Title of Invention	SUBSTITUTED PYRAZOLECARBOXYLIC ACID ANILIDE DERIVATIVE OR SALT THEREOF, INTERMEDIATE THEREOF, AGENT FOR AGRICULTURAL AND HORTICULTURAL USE, AND USE THEREOF
Abstract	Disclosed is a substituted pyrazolecarboxylic acid anilide derivative represented by the general formula (I) below or a salt thereof, which has excellent effects as a pesticide or acaricide for agricultural and horticultural use. (I) (In the formula, R1 represents H, an alkyl, an alkylcarbonyl, an alkenylcarbonyl, a cycloalkyl, a phenylalkyl, a phenylcarbonyl or the like; R2 represents H, a halogen, an alkyl, CN, OH, an alkoxy, a phenoxy, a phenylthio, a phenylsulfonyl or the like; G represents an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a C3-C10 cycloalkenyl or the like; Z represents O or S; X represents H, a halogen, CN, NO2, an alkyl or the like; Y1 represents H, an alkyl, an alkenyl, a phenyl, an alkoxyalkyl or the like; Y2 represen...

Title of Invention

SUBSTITUTED PYRAZOLECARBOXYLIC ACID ANILIDE DERIVATIVE OR SALT THEREOF, INTERMEDIATE THEREOF, AGENT FOR AGRICULTURAL AND HORTICULTURAL USE, AND USE THEREOF

Abstract

Disclosed is a substituted pyrazolecarboxylic acid anilide derivative represented by the general formula (I) below or a salt thereof, which has excellent effects as a pesticide or acaricide for agricultural and horticultural use. (I) (In the formula, R1 represents H, an alkyl, an alkylcarbonyl, an alkenylcarbonyl, a cycloalkyl, a phenylalkyl, a phenylcarbonyl or the like; R2 represents H, a halogen, an alkyl, CN, OH, an alkoxy, a phenoxy, a phenylthio, a phenylsulfonyl or the like; G represents an alkyl, an alkenyl, an alkynyl, a cycloalkyl, a C3-C10 cycloalkenyl or the like; Z represents O or S; X represents H, a halogen, CN, NO2, an alkyl or the like; Y1 represents H, an alkyl, an alkenyl, a phenyl, an alkoxyalkyl or the like; Y2 represen...

Full Text	DESCRIPTION SUBSTITUTED PYRAZOLECARBOXYLIC ACID ANILIDE DERIVATIVE OR SALT THEREOF, INTERMEDIATE THEREOF, AGENT FOR AGRICULTURAL AND HORTICULTURAL USE, AND USE THEREOF Technical Field The present invention relates to substituted pyrazolecarboxanilide derivatives or salts thereof, intermediates thereof, and agrohorticultural agents, particularly insecticides or acaricides, containing said compounds as an active ingredient and method for use thereof. Background Art Conventionally, substituted pyrazolecarboxamide derivatives similar to the present invention are known to be useful as agrohorticultural insecticides, fungicides or acaricides (e.g., JP-A-2003-48878, JP-A-2004-189738 and JP-A- 2004-269515). In JP-A-2003-48878, the substituted pyrazolecarboxanilide derivatives are disclosed. However, the substituents in the aniline moiety are mostly limited to the 2-position substituents, the 3-position substituent is methyl group alone, and the compound described in the present invention, wherein alkyl group having 2 or more carbon atoms is introduced into the 3-position is not included even in its compound list. Moreover, the 3-position methyl form concretely disclosed therein does not show an acaricide activity. In JP- A-2004-189738, substituted pyrazolecarboxanilide derivatives are disclosed. However, the substituents in the aniline moiety are limited to alkoxy group, alkylthio group and alkylamino group, and the compound described in the present invention, wherein alkyl group having 2 or more carbon atoms is directly introduced into the 3-position is not included even in its compound list. In JP-A-2004-269515, substituted pyrazolecarboxamide derivatives are disclosed. However, only an amide compound with heterocyclyl amine is disclosed, and the substituted pyrazolecarboxanilide derivatives of the present invention are not disclosed. Disclosure of the Invention In crop manufacturing in agricultural and horticultural fields, damages caused by insect pests are still serious, and development of novel agrohorticultural agents, particularly 1 development of insecticides and acaricides is desired due to generation of insect pests resistant to known agents, and the like. Since various labor saving farm works are required due to increasing numbers of the aged farm working population, creation of agrohorticultural agents with properties suitable for such labor saving farm works, particularly insecticides and acaricides, is also demanded. The present inventors have continued extensive studies on development of novel agrohorticultural agents, particularly insecticides and acaricides and have found, as the result, that among broad range of compounds described in the aforementioned prior document, a substituted pyrazolecarboxanilide derivative represented by the formula (I), in which a pyrazole ring is selected as the heterocyclic carboxylic acid moiety and a specific substituent is introduced into the aniline moiety at 3-position, showed excellent control effect as acaricides, not predicted at all from the content described in the aforementioned prior art references. Further, the inventors have found that an intermediate of said compound, i.e. a substituted aniline derivatives represented by the formula (II), and 1,3-dimethyl- 5-trifluoromethylpyrazole-4-carboxylic acid or salt thereof were novel compounds unknown in prior references, and were useful as intermediates for manufacturing various derivatives having physiological activities such as pharmaceuticals, pesticides and the like, and thus completed the present invention. wherein R1 is la) a hydrogen atom, 2a) a Ci-C8 alkyl group, 3a) a halo 2 Accordingly, the present invention relates to substituted pyrazolecarboxanilide derivatives represented by the formula (I): Ci-C6 alkyl group, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo Ci-C6 alkylcarbonyl group, 6a) a C2-C6 alkenylcarbonyl group, 7a) a halo C2-C6 alkenylcarbonyl group, 8a) a Ci-C6 alkylcarbonyl Ci-C6 alkyl group, 9a) a C3-C6 cycloalkyl group, 10a) a halo C3-C6 cycloalkyl group, 11a) a C3-C6 cycloalkyl Ci-C6 alkyl group, 12a) a halo C3-Cs cycloalkyl Ci-C6 alkyl group, 13a) a C2-C6 alkenyl group, 14a) a halo C2-C5 alkenyl group, 15a) a C2-C6 alkynyl group, 16a) a halo C2-C6 alkynyl group, 17a) a Ci-Cio alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy Ci-C6 alkyl group, 20a) a C1-C6 alkoxy Ci-Cs alkoxy C1-C6 alkyl group, 21a) a Ci-C6 alkylthio Ci-C6 alkyl group, 22a) a halo Ci-C6 alkylthio Ci-C6 alkyl group, 23a) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 24a) a halo Ci-C6 alkylsulf inyl C1-C6 alkyl group, 25a) a Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 26a) a halo Ci-C6 alkylsulfonyl C1-C6 alkyl group, 27a) a mono C1-C6 alkylamino C1-C6 alkyl group, 28a) a di Ci-C6 alkylamino Ci-C6 alkyl group wherein the alkyl groups are the same or different, 29a) a phenyl Ci-C6 alkoxy Ci-C6 alkyl group, 30a) a substituted phenyl Ci-C6 alkoxy Ci-Cs alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulf inyl group, k) a halo Ci-Cs alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6 alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group, 34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6 alkylthiocarbonyl group, 3 6a) a mono Ci-C6 alkylaminocarbonyl group, 37a) a di Ci-C6 alkylaminocarbonyl group wherein the alkyl groups are the same or different, 38a) a Ci-C6 alkoxycarbonyl Ci-C6 alkyl group, 39a) a Ci-C6 alkylsulfonyl group, 40a) a halo Ci-C6 alkylsulfonyl group, 41a) a cyano Ci-C6 alkyl group, 42a) a phenyl Ci-C6 alkyl group, 43a) a substituted phenyl Ci-C6 alkyl group having, on the ring, one 3 or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a substituted phenylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a) a substituted heterocyclylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci~ C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl 4 group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 50a) a phenoxy C1-C6 alkylcarbonyl group, 51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C5 alkoxycarbonyl group, 54a) a di Ci-C6 alkylphosphono group wherein the alkyl groups are the same or different, 55a) a di Ci-C6 alkylphosphonothio group wherein the alkyl groups are the same or different, 56a) a N-Ci-C6 alkyl-N-Ci-C6 alkoxycarbonylaminothio group, 57a) a N-Ci-C6 alkyl-W-Ci-C6 alkoxycarbonyl Ci-C6 alkylaminothio group, 58a) a di Ci-C6 alkylaminothio group wherein the alkyl groups are the same or different, 59a) a C3-C6 cycloalkylcarbonyl group, 60a) a halo C3-C6 cycloalkylcarbonyl group, 61a) a C1-C6 alkyl C3-C6 cycloalkylcarbonyl group, 62a) a halo Ci-C6 alkyl C3-C6 cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano 5 group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 67a) a C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl group, 69a) a halo C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group, 70a) a phenoxy Ci-C6 alkoxycarbonyl group, 71a) a substituted phenoxy C1-C6 alkoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 72a) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl group, 73a) a Ci-C6 alkylcarbonyl Ci-Ce alkylcarbonyl group, or 74a) a Ci-C6 alkoxycarbonyl C1-C6 alkylcarbonyl group; R2 is lb) a hydrogen atom, 2b) a halogen atom, 3b) a Ci-C6 alkyl group, 4b) a halo Ci-C6 alkyl group, 5b) a cyano group, 6b) a hydroxy group, 7b) a Ci-C6 alkoxy group, 8b) a halo Ci-C6 alkoxy 6 group, 9b) a Ci-C6 alkoxy C1-C3 alkoxy group, 10b) a halo Ci-C6 alkoxy C1-C3 alkoxy group, lib) a Ci-C6 alkylthio C1-C3 alkoxy group, 12b) a halo Ci-C6 alkylthio C1-C3 alkoxy group, 13b) a Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 14b) a halo Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 15b) a Ci-C6 alkylsulfonyl d- C3 alkoxy group, 16b) a halo C1-C6 alkylsulfonyl C1-C3 alkoxy group, 17b) a mono Ci-C6 alkylamino C1-C3 alkoxy group, 18b) a di C1-C6 alkylamino C1-C3 alkoxy group wherein the alkyl groups are the same or different, 19b) a Ci-C6 alkylthio group, 20b) a halo Ci-C6 alkylthio group, 21b) a C1-C6 alkylsulfinyl group, 22b) a halo Ci-C6 alkylsulfinyl group, 23b) a Ci-C6 alkylsulfonyl group, 24b) a halo Ci-C6 alkylsulfonyl group, 25b) an amino group, 2 6b) a mono Ci-C6 alkylamino group, 27b) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, 28b) a phenoxy group, 29b) a substituted phenoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Cx-C6 alkoxycarbonyl group, 30b) a phenylthio group, 31b) a substituted phenylthio group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 32b) a phenylsulfinyl group, 33b) a substituted phenylsulfinyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 7 alkyl group, e) a halo C1-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 34b) a phenylsulfonyl group, 35b) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 36b) a phenyl C1-C6 alkoxy group, or 37b) a substituted phenyl Ci-C6 alkoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci- C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group; G is lc) a C2-Cio alkyl group, 2c) a halo C2-Cio alkyl group, 3c) a C3-C10 alkenyl group, 4c) a halo C3-C10 alkenyl group, 5c) a C3-C10 alkynyl group, 6c) a halo C3-C10 alkynyl group, 7c) a C3- C10 cycloalkyl group, 8c) a substituted C3-C10 cycloalkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a Ci-C6 alkyl group, and c) a halo Ci-C6 alkyl group, 9c) a C3-C10 cycloalkenyl group, 10c) a substituted C3-C10 cycloalkenyl group having, on the ring, one or more, the same or different 8 substituents selected from a) a halogen atom, b) a Ci-C6 alkyl group, and c) a halo Ci-C6 alkyl group, lie) a C3-C8 cycloalkyl Ci-C6 alkyl group, or 12c) a halo C3-C8 cycloalkyl Ci-C6 alkyl group; Z is an oxygen atom or a sulfur atom; X may be the same or different and is Id) a hydrogen atom, 2d) a halogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a Ci- C6 alkyl group, or 6d) a halo C1-C6 alkyl group; Y1 is le) a hydrogen atom, 2e) a Ci-C6 alkyl group, 3e) a halo Ci-C6 alkyl group, 4e) a C2-C6 alkenyl group, 5e) a halo C2-C6 alkenyl group, 6e) a C2-C6 alkynyl group, 7e) a halo C2-Cs alkynyl group, 8e) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group, 9e) a hydroxy Ci-C6 alkyl group, lOe) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl group, lie) a C3-C6 cycloalkyl group, 12e) a halo C3-C5 cycloalkyl group, 13e) a C3-C6 cycloalkyl Ci-C6 alkyl group, 14e) a halo C3-C6 cycloalkyl Ci-C6 alkyl group, 15e) a Ci-C6 alkylsulfonyl group, 16e) a halo C1-C6 alkylsulfonyl group, 17e) a Ci-C6 alkylthio Ci-C6 alkyl group, 18e) a halo C1-C6 alkylthio Ci-C6 alkyl group, 19e) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 20e) a halo C1-C6 alkylsulf inyl Ci-C6 alkyl group, 21e) a Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 22e) a halo Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 23e) a mono Ci-C6 alkylamino Ci-C6 alkyl group, 24e) a di Ci-C6 alkylamino Ci-C6 alkyl group wherein the alkyl groups are the same or different, 25e) a phenyl group, 2 6e) a substituted phenyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulf inyl group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group; Y2 may be the same or different and is If) a hydrogen atom, 2f) a halogen atom, 3f) a cyano group, 4f) a nitro group, 5f) a hydroxyl group, 6f) a mercapto group, 7f) an amino group, 8f) a carboxyl group, 9f) a Ci-C6 alkyl group, lOf) a halo Ci-C6 9 alkyl group, llf) a C2-C6 alkenyl group, 12f) a halo C2-C6 alkenyl group, 13f) a C2-C6 alkynyl group, 14f) a halo C2-Cs alkynyl group, 15f) a tri C1-C6 alkylsilyl C2-C6 alkynyl group wherein the alkyl groups are the same or different, 16f) a phenyl C2-C6 alkynyl group, 17f) a Ci-C6 alkoxy Ci-C6 alkoxy Ci- C6 alkyl group, 18f) a hydroxy Ci-C6 alkyl group, 19f) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl group, 20f) a C3-C6 cycloalkyl group, 21f) a halo C3-C6 cycloalkyl group, 22f) a C3-C6 cycloalkyl Ci-C6 alkyl group, 23f) a halo C3-C6 cycloalkyl Ci-C6 alkyl group, 24f) a Ci-C6 alkoxy group, 25f) a halo C1-C6 alkoxy group, 26f) a Ci-C6 alkoxy Ci-C6 alkoxy group, 27f) a halo Ci-C6 alkoxy Ci-C6 alkoxy group, 28f) a phenyl Ci-C6 alkoxy group, 29f) a Ci-Cs alkoxy Ci-C6 alkyl group, 30f) a halo Ci-C6 alkoxy Ci-Cg alkyl group, 31f) a Ci-C6 alkylthio group, 32f) a halo Ci~ C6 alkylthio group, 33f) a Ci-C6 alkylsulfinyl group, 34f) a halo Ci-C6 alkylsulfinyl group, 35f) a Ci-C6 alkylsulfonyl group, 36f) a halo Ci-C6 alkylsulfonyl group, 37f) a Ci-C6 alkylthio Ci-C6 alkyl group, 38f) a halo Ci-C6 alkylthio Ci-C6 alkyl group, 39f) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 40f) a halo Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 41f) a Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 42f) a halo Ci-C6 alkylsulfonyl C1-C6 alkyl group, 43f) a mono Ci-C6 alkylamino group, 44f) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, 45f) a phenylamino group, 4 6f) a mono Ci-C6 alkylamino Ci-C6 alkyl group, 47f) a di C1-C6 alkylamino Ci-C6 alkyl group wherein the alkyl groups are the same or different, 48f) a phenyl group, 49f) a substituted phenyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci~C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 50f) a phenoxy group, 51f) a substituted phenoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a 10 cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-Cs alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 52f) a heterocyclic group, or 53f) a substituted heterocyclic group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group; m is 1 or 2; and n is an integer of 1-3, salts thereof and agrohorticultural agents containing the compound as an active ingredient, and methods of use thereof. In addition, the present invention also relates to substituted aniline derivatives represented by the formula (II), which are intermediates therefor: wherein R1 is la) a hydrogen atom, 2a) a Ci-C8 alkyl group, 3a) a halo C1-C6 alkyl group, 4a) a C1-C6 alkylcarbonyl group, 5a) a halo Ci-C6 alkylcarbonyl group, 6a) a C2-C6 alkenylcarbonyl group, 7a) a halo C2-C6 alkenylcarbonyl group, 8a) a Ci-C6 alkylcarbonyl Ci-C6 alkyl group, 9a) a C3-C6 cycloalkyl group, 10a) a halo C3-C6 cycloalkyl group, 11a) a C3-C6 cycloalkyl C1-C6 11 alkyl group, 12a) a halo C3-C6 cycloalkyl Ci-C6 alkyl group, 13a) a C2-C6 alkenyl group, 14a) a halo C2-C6 alkenyl group, 15a) a C2-C6 alkynyl group, 16a) a halo C2-C6 alkynyl group, 17a) a C1-C10 alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy Ci-C6 alkyl group, 20a) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-Cs alkyl group, 21a) a Ci-C6 alkylthio Ci-C6 alkyl group, 22a) a halo Ci-C6 alkylthio Ci-C6 alkyl group, 23a) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 24a) a halo Ci-C6 alkylsulf inyl Ci-C6 alkyl group, 25a) a C1-C6 alkylsulfonyl Ci-C6 alkyl group, 2 6a) a halo Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 27a) a mono Ci-C6 alkylamino Ci-C6 alkyl group, 28a) a di Ci-C6 alkylamino Ci-C6 alkyl group wherein the alkyl groups are the same or different, 29a) a phenyl Ci-C6 alkoxy Ci-C6 alkyl group, 30a) a substituted phenyl Ci-C6 alkoxy Ci-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 31a) a C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6 alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group, 34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6 alkylthiocarbonyl group, 3 6a) a mono Ci-C6 alkylaminocarbonyl group, 37a) a di Ci-C6 alkylaminocarbonyl group wherein the alkyl groups are the same or different, 38a) a Ci-C6 alkoxycarbonyl Ci-C6 alkyl group, 39a) a Ci-C6 alkylsulfonyl group, 40a) a halo C1-C6 alkylsulfonyl group, 41a) a cyano Ci-C6 alkyl group, 42a) a phenyl C1-C6 alkyl group, 43a) a substituted phenyl Ci-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, 12 k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a substituted phenylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a) a substituted heterocyclylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci- C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C5 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 50a) a phenoxy Ci-C6 alkylcarbonyl group, 51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on 13 the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci~C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 54a) a di Ci-C6 alkylphosphono group wherein the alkyl groups are the same or different, 55a) a di Ci-C6 alkylphosphonothio group wherein the alkyl groups are the same or different, 56a) a N-Ci-C6 alkyl-N-Ci-C6 alkoxycarbonylaminothio group, 57a) a N-C1-C6 alkyl-N-Ci-C6 alkoxycarbonyl Ci-C6 alkylaminothio group, 58a) a di Ci-C6 alkylaminothio group wherein the alkyl groups are the same or different, 59a) a C3-Cs cycloalkylcarbonyl group, 60a) a halo C3-C6 cycloalkylcarbonyl group, 61a) a Ci-C6 alkyl C3-C6 cycloalkylcarbonyl group, 62a) a halo Ci-C6 alkyl C3-C6 cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo 14 Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 67a) a C3-C6 cycloalkyl C1-C6 alkylcarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl group, 69a) a halo C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group, 70a) a phenoxy Ci-C6 alkoxycarbonyl group, 71a) a substituted phenoxy Ci-C6 alkoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 72a) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl group, 73a) a Ci-C6 alkylcarbonyl C1-C6 alkylcarbonyl group, or 74a) a Ci-C6 alkoxycarbonyl Ci-C6 alkylcarbonyl group; R2 is lb) a hydrogen atom, 2b) a halogen atom, 3b) a Ci-C6 alkyl group, 4b) a halo Ci-C6 alkyl group, 5b) a cyano group, 6b) a hydroxy group, 7b) a Ci-C6 alkoxy group, 8b) a halo Ci-C6 alkoxy group, 9b) a Ci-C6 alkoxy C1-C3 alkoxy group, 10b) a halo C1-C6 alkoxy C1-C3 alkoxy group, lib) a C1-C6 alkylthio C1-C3 alkoxy group, 12b) a halo Ci-C6 alkylthio C1-C3 alkoxy group, 13b) a Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 14b) a halo Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 15b) a Ci-C6 alkylsulfonyl Ci- 15 C3 alkoxy group, 16b) a halo Ci-C6 alkylsulfonyl C1-C3 alkoxy group, 17b) a mono Ci-C6 alkylamino C1-C3 alkoxy group, 18b) a di Ci-C6 alkylamino C1-C3 alkoxy group wherein the alkyl groups are the same or different, 19b) a Ci-C6 alkylthio group, 20b) a halo Ci-C6 alkylthio group, 21b) a Ci-C6 alkylsulfinyl group, 22b) a halo Ci-C6 alkylsulfinyl group, 23b) a Ci-C6 alkylsulfonyl group, 24b) a halo Ci-C6 alkylsulfonyl group, 25b) an amino group, 2 6b) a mono C1-C6 alkylamino group, 27b) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, 28b) a phenoxy group, 29b) a substituted phenoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-Cs alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 30b) a phenylthio group, 31b) a substituted phenylthio group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 32b) a phenylsulfinyl group, 33b) a substituted phenylsulfinyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 16 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 34b) a phenylsulfonyl group, 35b) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulf onyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 36b) a phenyl Ci-C6 alkoxy group, or 37b) a substituted phenyl Ci-C6 alkoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci- C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group; G is lc) a C2-Cio alkyl group, 2c) a halo C2-Ci0 alkyl group, 3c) a C3-C10 alkenyl group, 4c) a halo C3-C10 alkenyl group, 5c) a C3-C10 alkynyl group, 6c) a halo C3-C10 alkynyl group, 7c) a C3- C10 cycloalkyl group, 8c) a substituted C3-C10 cycloalkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a Ci-C6 alkyl group, and c) a halo Ci-C6 alkyl group, 9c) a C3-C10 cycloalkenyl group, 10c) a substituted C3-C10 cycloalkenyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a Ci-C6 alkyl group, and c) a halo C1-C6 alkyl group, lie) a C3-C8 cycloalkyl Ci-C6 alkyl group, or 12c) a halo C3-Ce cycloalkyl Ci-C6 alkyl group; X may be the same or different and is Id) a hydrogen atom, 2d) 17 a halogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a Ci- C6 alkyl group, or 6d) a halo C1-C6 alkyl group; n is an integer of 1-3, salts thereof and 1,3-dimethyl-5-trifluoromethylpyrazole-4- carboxylic acid and a salt thereof. Best Mode for Embodying the Invention In the definitions of a substituted pyrazolecarboxanilide derivative of the formula (I) and a substituted aniline derivative of the formula (II) of the present invention, "halo", "Ci-C6 alkyl", "Ci-C6 alkoxyl", "C2-C6 alkenyl", "C2-C6 alkynyl" or "a heterocyclic group", and the like in each of substituents has the following meaning. The "halo" or "halogen atom" means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom. The "Ci-C6 alkyl" is linear or branched chain alkyl having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, 2-methylbutyl, 1-ethylpropyl, n-hexyl, 2-ethylbutyl and the like. The "Ci-C8 alkyl" is linear or branched chain alkyl having 1 to 8 carbon atoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, 2-methylbutyl, 1-ethylpropyl, n-hexyl, 2-ethylbutyl, n-heptyl, n-octyl, 2-ethylhexyl and the like. The "C2-C10 alkyl" is linear or branched chain alkyl having 2 to 10 carbon atoms, such as ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, 2-methylbutyl, n-hexyl, 2-ethylbutyl, 1- ethylpropyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl and the like. The "C3-C6 cycloalkyl" is cyclic alkyl having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. The "C3-Ce cycloalkyl" is cyclic alkyl having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like. The "C3-C10 cycloalkyl" is cyclic alkyl having 3 to 10 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, 18 cyclohexyl, cyclooctyl, cyclodecyl and the like. The "C3-C10 cycloalkenyl" is cyclic alkenyl having 3 to 10 carbon atoms, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclooctenyl, cyclodecenyl and the like. The "C1-C3 alkoxy" is alkoxy wherein its alkyl moiety is linear or branched chain alkyl having 1 to 3 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy and the like. The "Ci-C6 alkoxy" is alkoxy wherein its alkyl moiety is the above-mentioned "Ci-C6 alkyl", such as methoxy, ethoxy, n- propoxy, i-propoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, 2- methylbutoxy, 1-ethylpropoxy, hexyloxy, 2-ethylbutoxy and the like. The "C1-C10 alkoxy" is alkoxy wherein its alkyl moiety is linear or branched chain alkyl having 1 to 10 carbon atoms, such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, 2-methylbutoxy, 1-ethylpropoxy, hexyloxy, 2-ethylbutoxy, n-heptyloxy, n-octyloxy, 2- ethylhexyloxy, n-nonyloxy, n-decyloxy and the like. The "C1-C16 alkoxy" is alkoxy wherein its alkyl moiety is linear or branched chain alkyl having 1 to 16 carbon atoms, such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, 2-methylbutoxy, 1-ethylpropoxy, hexyloxy, 2-ethylbutoxy, n-heptyloxy, n-octyloxy, 2- ethylhexyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n- dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy and the like. The "C2-C6 alkenyl" is linear or branched chain alkenyl having 2 to 6 carbon atoms, which has at least one double bond, such as vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3- butenyl, 2-pentenyl, 2-methyl-1-propenyl, 2,4-pentadienyl, 3- hexenyl and the like. The "C3-C10 alkenyl" is linear or branched chain alkenyl having 3 to 10 carbon atoms, which has at least one double bond, such as 1-butenyl, 2-butenyl, 3-butenyl, 2-pentenyl, 2,4-pentadienyl, 3-hexenyl, 3-heptenyl, 3-octenyl, 3-nonenyl, 19 3-decenyl and the like. The "C2-C6 alkynyl" is linear or branched chain alkynyl having 2 to 6 carbon atoms, which has at least one triple bond, such as ethynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 2-pentynyl, 3-hexynyl and the like. The "C3-C10 alkynyl" is linear or branched chain alkynyl having 3 to 10 carbon atoms, which has at least one triple bond, such as 1-butynyl, 2-butynyl, 3-butynyl, 2-pentynyl, 3- hexynyl, 3-heptynyl, 3-octynyl, 3-nonynyl, 3-decynyl and the like. The numbers in "C2-C6", "C3-C10" and the like shows the range of carbon atom numbers such as 2 to 6 carbon atoms and 3 to 10 carbon atoms. Moreover, the above-mentioned definitions can apply to groups wherein the above-mentioned substituents are connected. For example, "halo C1-C6 alkyl" means linear or branched chain alkyl group having 1 to 6 carbon atoms, which is substituted by the same or different one or more halogen atoms, such as chloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 3- chloropropyl, 2-chloro-l,1-dimethylethyl, 1-bromo-l- methylethyl, difluoromethyl, trifluoromethyl, 2,2,2- trifluoroethyl, perfluorohexyl and the like. "A heterocyclic group" and "A heterocyclyl" are 5- or 6- membered heterocyclic groups having one or more hetero atoms selected from an oxygen atom, a sulfur atom and a nitrogen atom including, for example, pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydrofuryl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, triazolyl group and pyrazolyl group. A salt of a substituted pyrazolecarboxanilide derivative represented by the formula (I) of the present invention includes a salt of an alkali metal (lithium, sodium, potassium, etc.); a salt of an alkaline earth metal (calcium, magnesium, etc.); an ammonium salt; and a salt of an organic amine (methylamine, triethylamine, diethanolamine, piperidine, pyridine, etc.), or an acid addition salt. The acid addition 20 salt includes, for example, a carboxylate such as acetate, propionate, oxalate, trifluoroacetate, benzoate and the like; a sulfonate such as methanesulfonate, trifluoromethanesulfonate, p-toluenesulfonate and the like; an inorganic acid salt such as a hydrochloride, a sulfate, a nitrate, a carbonate and the like. In the substituted pyrazolecarboxanilide derivatives represented by the formula (I) of the present invention, R1 is preferably la) a hydrogen atom, 2a) a Ci-C6 alkyl group, 3a) a halo C1-C6 alkyl group, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo Ci-C6 alkylcarbonyl group, 6a) a C2-C6 alkenylcarbonyl group, 13a) a C2-C6 alkenyl group, 17a) a C1-C10 alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 19a) a C2~C6 alkenyloxy C1-C6 alkyl group, 20a) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group, 29a) a phenyl Ci-C6 alkoxy Ci-C6 alkyl group, 30a) a substituted phenyl C1-C6 alkoxy C1-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6 alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group, 34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6 alkylthiocarbonyl group, 42a) a phenyl Ci-C6 alkyl group, 43a) a substituted phenyl Ci-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the 21 same or different, and p) a Ci-C6 alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a substituted phenylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a) a substituted heterocyclylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, 0) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 50a) a phenoxy Ci-C6 alkylcarbonyl group, 51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 22 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-Cs alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 58a) a di Ci-C6 alkylaminothio group wherein the alkyl groups are the same or different, 59a) a C3-C6 cycloalkylcarbonyl group, 61a) a Ci-C6 alkyl C3-C6 cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci~C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-Cs alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a phenyl C3~C6 cycloalkylcarbonyl group, 66a) a substituted phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-Cs alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl 23 group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl group, 73a) a Ci-C6 alkylcarbonyl Ci-Cs alkylcarbonyl group, or 74a) a Ci-C6 alkoxycarbonyl Ci-C6 alkylcarbonyl group, and more preferably la) a hydrogen atom, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo Ci-C6 alkylcarbonyl group, 17a) a Ci-Cio alkoxy Ci-C6 3alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, ^Oa) a C1-C16 alkoxycarbonyl group,, ^?a) a halo Ci-C6 alkoxycarbonyl group or 6 R2 is preferably lb) a hydrogen atom, 2b) a halogen atom, 6b) a hydroxy group, 7b) a Ci-C6 alkoxy group or 8b) a halo Ci- C6 alkoxy group, and more preferably lb) a hydrogen atom or 7b) a Ci-C6 alkoxy group. G is preferably lc) a C2-Ci0 alkyl group, 3c) a C3-C10 alkenyl group, or lie) a C3-C8 cycloalkyl Ci-C6 alkyl group, and more preferably lc) a C2-Cio alkyl group. X is preferably Id) a hydrogen atom, 2d) a halogen atom, or 5d) a Ci-C6 alkyl group, and more preferably Id) a hydrogen atom. Z is preferably an oxygen atom. Y1 is preferably 2e) a Ci-C6 alkyl group, 3e) a halo Ci-C6 alkyl group, or 4e) a C2-C6 alkenyl group, and more preferably 2e) a Ci-C6 alkyl group. Y2 is preferably If) a hydrogen atom, 2f) a halogen atom, 9f) a Ci-C6 alkyl group, lOf) a halo Ci-C6 alkyl group, or 31f) a Ci-C6 alkylthio group, and more preferably If) a hydrogen atom, 2f) a halogen atom, 9f) a Ci-C6 alkyl group, or lOf) a halo Ci-C6 alkyl group. m is preferably 2. In addition, a salt of a substituted aniline derivative represented by the formula (II) is preferably an acid addition salt including, for example, a carboxylate such as acetate, propionate, oxalate, trifluoroacetate, benzoate and the like; a sulfonate such as methanesulfonate, trifluoromethanesulfonate, p-toluenesulfonate and the like; an inorganic acid salt such as a hydrochloride, a sulfate, a nitrate, a carbonate and the like. 24 A salt of 1,3-dimethyl-5-trifluoromethylpyrazole-4- carboxylic acid of the present invention includes a salt of an alkali metal (lithium, sodium, potassium, etc.); a salt of an alkaline earth metal (calcium, magnesium, etc.); an ammonium salt; and a salt of an organic amine (methylamine, triethylamine, diethanolamine, piperidine, pyridine, etc.). A substituted pyrazolecarboxanilide derivative represented by the formula (I) or an intermediate thereof, i.e. a substituted aniline derivative represented by the formula (II), of the present invention may contain one or plural numbers of asymmetric centers in the structural formula, and further two or more optical isomers and diastereomers may be present. Consequently, the present invention entirely encompasses each optical isomer and the mixtures with any ratio thereof. In addition, a substituted pyrazolecarboxanilide derivative represented by the formula (I) of the present invention may have two types of geometric isomers derived from a C-C double bond in the structural formula. The present invention encompasses all of geometric isomers and the mixtures containing them in any ratio. Moreover, the present invention encompasses hydrates thereof. Representative production methods for a substituted pyrazolecarboxanilide derivative represented by the formula (I) and a substituted aniline derivative represented by the formula (II), as an intermediate thereof are illustrated hereinbelow, but the present invention should not be construed as limiting thereto. 25 (wherein G, R1, X, n, Y1, Y2 and m are as defined above; and R3 is a hydrogen atom, a Ci-C6 alkyl group, a halo Ci-C6 alkyl group, a phenyl group, a substituted phenyl group or a phenyl C1-C4 alkyl group; W is -0-, -S- or -N(R4)-, wherein R4 is a hydrogen atom, a C1-C6 alkyl group, a halo Ci-C6 alkyl group, a phenyl group, a substituted phenyl group or a phenyl C1-C4 alkyl group; and Q is a halogen atom or a Ci-C6 alkoxyl group) . Among a substituted pyrazolecarboxanilide derivative represented by the formula (I), a substituted pyrazolecarboxanilide derivative (1-1) wherein Z is O, and R2 is a hydrogen atom, a fluorine atom or WR3 wherein W and R3 are as defined above can be produced by reacting an aniline derivative represented by the formulas (II-l) to (II-3) with a pyrazolecarboxylic halide or a pyrazolecarboxylate ester represented by the formula (III) in the presence or absence of a base in an inert solvent, or by reacting an aniline derivative represented by the formulas (II-l) to (II-3) with a pyrazolecarboxylic acid represented by the formula (IV) in the presence of a condensing agent, in the presence or absence of a base, in an inert solvent, and any usual production methods for amides may be applicable. An aniline derivative represented by the formula (II-2) can be produced by reducing an aniline derivative represented by the formula (II-l) in the presence of a reducing agent, in an inert solvent. An aniline derivative represented by the formula (II-3) 26 can be produced by reacting an aniline derivative represented by the formula (II-l) with an alcohol derivative, a thiol derivative or an amine derivative represented by the formula (V), in the presence or absence of a base in an inert solvent. The formula (II-l) -> the formula (II-2) An example of a reducing agent to be used in the present reaction includes metal hydrides such as lithium aluminum hydride, lithium borohydride, sodium borohydride, diisobutyl aluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride and the like, metal such as lithium and the like or metal salts, and the like. The amount of the reducing agent to be used may be selected, as appropriate, in the range from equivalent to excess amount relative to an aniline derivative represented by the formula (II-l). An example of an inert solvent to be used in the present reaction, which may be any one as long as it does not significantly inhibit progress of the present reaction, includes aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and the like; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and the like; straight chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and the like, or dimethylsulfoxide and the like and these inert solvents can be used alone or in combination of two or more kinds. Reaction temperature may be in the range from room temperature to boiling temperature of an inert solvent to be used and reaction time may be in the range from several minutes to 50 hours, while depending on reaction scale and reaction temperature. After completion of the reaction, desired compound may be isolated from the reaction mixture by a conventional method and the desired compound can be produced by purification using recrystallization or column chromatography, etc, if necessary. The desired compound may also be subjected to subsequent reaction step without isolation from the reaction mixture. 27 The formula (II-l) -> the formula (II-3) An example of a base to be used in the present reaction includes metal hydrides such as lithium hydride, sodium hydride, potassium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert- butoxide and the like; and alkyl metals such as n-butyl lithium, sec-butyl lithium, tert-butyl lithium and the like. The amount of the base to be used may be selected, as appropriate, in the range from equivalent to excess amount relative to an aniline derivative represented by the formula (II-D • As an example of an inert solvent to be used in the present reaction, which may be any one as long as it does not significantly inhibit progress of the present reaction, includes aromatic hydrocarbons such as benzene, toluene, xylene and the like; alcohols such as methanol, ethanol and the like; straight chain or cyclic ethers such as diethyl ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran and the like, and the like and these inert solvents can be used alone or in combination of two or more kinds. Reaction temperature may be in the range from -70°C to boiling temperature of an inert solvent to be used and reaction time may be in the range from several minutes to 50 hours, while depending on reaction scale and reaction temperature. After completion of the reaction, desired compound may be isolated from the reaction mixture by a conventional method and the desired compound can be produced by purification using recrystallization or column chromatography, etc, if necessary. The desired compound may also be subjected to subsequent reaction step without isolation from the reaction mixture. The formula (II-l), (II-2) or (II-3) -> the formula (1-1) An example of a condensing agent to be used in the present reaction includes diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), chloroformates, 2-chloro-l-methylpyridinium iodide and the like. As a base to be used in the present reaction, an inorganic base or an organic base is included and an example 28 of an inorganic base includes alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; alkali metal hydrides such as sodium hydride, potassium hydride and the like; alkali metal salts of alcohol such as sodium ethoxide, potassium tert-butoxide and the like; carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and the like; and an example of organic bases includes triethylamine, pyridine, DBU and the like. The amount of the base to be used may be selected in the range from equivalent to excess amount relative to a pyrazolecarboxylic acid derivative represented by the formula (III) or (IV) . An example of an inert solvent to be used in the present reaction, which may be any one as long as it does not significantly inhibit progress of the present reaction, includes aromatic hydrocarbons such as benzene, toluene, xylene and the like; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and the like; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and the like; straight chain or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran and the like; esters such as ethyl acetate and the like; amides such as dimethylformamide, dimethylacetamide and the like; dimethylsulfoxide; 1,3-dimethyl-2-imidazolidinone; acetone, methyl ethyl ketone and the like. These inert solvents can be used alone or in combination of two or more kinds. As the present reaction is an equimolar reaction, each reactant may be used in equal mole, however, any of the reactants may also be used in excess. Reaction temperature may be in the range from room temperature to boiling temperature of an inert solvent to be used and reaction time may be in the range from several minutes to 48 hours, while depending on reaction scale and reaction temperature. After completion of the reaction, desired compound may be isolated from the reaction mixture by a conventional method and the desired compound can be produced by purification using recrystallization or column chromatography, etc, if necessary. An aniline derivative represented by the formula (II-l), as a raw material of the present reaction, can be produced in accordance with a production method disclosed in JP-A-11- 29 302233, JP-A-2001-122836 or JP-A-2006-8675. A pyrazolecarboxylic acid derivative represented by the formulas (III) or (IV) can be produced in accordance with several methods described in known literatures (for example, Aust. J. Chem., 1983, 36, 135-147, Synthesis, 1986, 753-755, JP-A-52-87168, JP-A-63-45264, JP-A-1-106866 and the like). (wherein G, R1, R2, X, n, Y1, Y2 and m are as defined above) . Among substituted pyrazolecarboxanilide derivatives represented by the formula (I), a substituted pyrazolecarboxanilide derivative (1-2) wherein Z is S can be produced by reacting an anilide derivative represented by (I- 1) with Lawesson's Reagent in accordance with a known method (Tetrahedron Lett., 21 (42), 4061 (1980)). (wherein G, R2, X, n, Y1, Y2, m and Q are as defined above and R1' is as defined above except a hydrogen atom). Among substituted pyrazolecarboxanilide derivatives represented by the formula (I), a substituted pyrazolecarboxanilide derivative (1-4) wherein R1 is other than a hydrogen atom can be produced by reacting an amide derivative represented by the formula (1-3) with a halide derivative or an ester derivative represented by the formula (VI) , in the presence or absence of a base, in an inert 30 solvent. As an example of a base to be used in the present reaction includes metal hydroxides such as sodium hydroxide, potassium hydroxide and the like; carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and the like; metal hydrides such as lithium hydride, sodium hydride, potassium hydride and the like; metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tert- butoxide and the like; alkyl metals such as n-butyl lithium, sec-butyl lithium, tert-butyl lithium and the like. The amount of the base to be used may be selected, as appropriate, in the range from equivalent to excess amount relative to an amide derivative represented by the formula (1-3). An example of an inert solvent to be used in the present reaction, which may be any one as long as it does not significantly inhibit progress of the present reaction, includes aromatic hydrocarbons such as benzene, toluene, xylene and the like; alcohols such as methanol, ethanol and the like; straight chain or cyclic ethers such as diethyl ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran and the like; amides such as dimethylformamide, dimethylacetamide and the like; dimethylsulfoxide; 1,3-dimethyl-2-imidazolidinone and the like. These inert solvents can be used alone or in combination of two or more kinds. Reaction temperature may be in the range from -70°C to boiling temperature of an inert solvent to be used and reaction time may be in the range from several minutes to 50 hours, while depending on reaction scale and reaction temperature. After completion of the reaction, desired compound may be isolated from the reaction mixture by a conventional method and the desired compound can be produced by purification using recrystallization or column chromatography, etc, if necessary. 31 (wherein G, R1, R3, X, n, Y1, Y2 and m are as defined above, and q is 1 or 2). A substituted pyrazolecarboxanilide derivatives represented by the formula (1-6) can be produced by reacting a sulfide derivative represented by the formula (1-5) which can be produced in Production method 1 with an oxidizing agent in the presence of an inert solvent An example of an inert solvent to be used in the present reaction includes halogenated hydrocarbons such as methylene chloride, chloroform and the like; aromatic hydrocarbons such as toluene, xylene and the like; halogenated aromatic hydrocarbons such as fluorobenzene, chlorobenzene, dichlorobenzene and the like; acids such as acetic acid and the like; alcohols such as methanol, ethanol, propanol and the like. An example of an oxidizing agent includes m- peroxychlorobenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulphate (Oxone), hydrogen peroxide and the like. The amount of the oxidizing agent to be used may be selected, as appropriate, in the range of 0.5 to 3 equivalents relative to a sulfide derivative represented by the formula (1-5). Reaction temperature may be in the range from -50°C to boiling temperature of an inert solvent to be used and reaction time may be in the range from several minutes to 24 hours, while depending on reaction scale and reaction temperature. After completion of the reaction, desired compound may be isolated from the reaction mixture by a conventional method and the desired compound can be produced by purification using recrystallization or column chromatography, etc, if necessary. 32 Typical compounds of substituted pyrazolecarboxanilide derivatives represented by the formula (I) are exemplified in Table 1 and Table 2, and typical compounds of substituted aniline derivatives represented by the formula (II) are exemplified in Table 3, and an substituted pyrazolecarboxylic acid derivative represented by the formula (IV) is exemplified in Table 4, however, the present invention should not be construed as limiting to these. In "property" column of Table 1 and Table 2, melting point (°C) or refractive index (nD(°C)) is shown and for compounds described as amorphous or paste, """H-NMR data thereof were shown in Table 5. In the Tables, "n-" is normal, and "i-" is iso, "t-" is tertiary, "c-" is cyclo, "Me" is a methyl group, "Et" is an ethyl group, "Pr" is a propyl group, "Bu" is a butyl group, "Pen" is a pentyl group, "Hex" is a hexyl group, "Ph" is a phenyl group, "Bn" is a benzyl group, "Ac" is an acetyl group and "Pyr" is a pyrazinyl group. 33 Table 1 (Xn=H) No. G Y1 Y2 1 m R1 R2 Property 1-1 Et Me 3, 5-Me2 H H 72-75 1-2 Et Me 3, 5-Me2 Ac H 1-3 Et Me 3, 5-Me2 H OMe 129-131 1-4 Et Me 3, 5-Me2 Ac OMe 1.5028(25.4) 1-5 Et Me 3; 5-Me2 COEt OMe 1-6 Et Me 3, 5-Me2 CO-c-Pr OMe 118.8-121.6 1-7 Et Me 3, 5-Me2 CH2OMe OMe 1-8 Et Me 3, 5-Me2 CH2OEt OMe 1.4889(24.2) 1-9 Et Me 3, 5-Me2 COOMe OMe 1-10 Et Me 3 5-Me2 COOEt OMe 77.2-79.2 1-11 Et Me 3, 5-Me2 COO-n-Pr OMe 1-12 Et Me 3 5-Me2 COO-i-Bu OMe 1.4895(25.4) 1-13 Et Me 3 5-Me2 H OEt 110-113 1-14 Et Me 3 5-Me2 Ac OEt 1-15 Et Me 3 , 5-Me2 COEt OEt 90-91 1-16 Et Me 3 , 5-Me2 CO-c-Pr OEt 119-120 1-17 Et Me 3 , 5-Me2 CH2OMe OEt 1-18 Et Me 3 , 5-Me2 CH2OEt OEt 1-19 Et Me 3 , 5-Me2 COOMe OEt 1-20 Et Me 3 , 5-Me2 COOEt OEt 1-21 Et Me 3 , 5-Me2 COO-n-Pr OEt 1-22 Et Me 3 , 5-Me2 COO-i-Bu OEt 1-23 Et Me 3- ZF3-5-Me H H 1.4768(21.8) 34 Table 1 (continued) No. G Y1 Y2 R1 R2 Property 1-24 Et Me 3-CF3-5-Me Ac H 132-134 1-25 Et Me 3-CF3-5-Me H OMe 57-60 1-26 Et Me 3-CF3-5-Me Ac OMe 1.4736(24.6) 1-27 Et Me 3-CF3-5-Me COEt OMe 134-135 1-28 Et Me 3-CF3-5-Me CO-c-Pr OMe 1.4830(26.2) 1-29 Et Me 3-CF3-5-Me CH2OMe OMe 1-30 Et Me 3-CF3-5-Me CH2OEt OMe 1-31 Et Me 3-CF3-5-Me COOMe OMe 128-130 1-32 Et Me 3-CF3-5-Me COOEt OMe 1.4697(25.9) 1-33 Et Me 3-CF3-5-Me COO-n-Pr OMe 1-34 Et Me 3-CF3-5-Me COO-i-Bu OMe 1.4681(26.2) 1-35 Et Me 3-CF3-5-Me H OEt 142-145 1-36 Et Me 3-CF3-5-Me Ac OEt 1.4720(24.5) 1-37 Et Me 3-CF3-5-Me COEt OEt 1.4710(26.9) 1-38 Et Me 3-CF3-5-Me CO-c-Pr OEt 1-39 Et Me 3-CF3-5-Me CH2OMe OEt 1-40 Et Me 3-CF3-5-Me CH2OEt OEt 1-41 Et Me 3-CF3-5-Me COOMe OEt 1-42 Et Me 3-CF3-5-Me COOEt OEt 1-43 Et Me 3-CF3-5-Me COO-n-Pr OEt 1-44 Et Me 3-CF3-5-Me COO-i-Bu OEt 1-45 n-Pr Me 3, 5-Me2 H H 167-168 1-46 n-Pr Me 3, 5-Me2 Ac H 1-47 n-Pr Me 3, 5-Me2 H OMe 184-185 1-48 n-Pr Me 3, 5-Me2 Ac OMe 1.4953(25.0) 1-49 n-Pr Me 3, 5-Me2 COEt OMe 1.4982 (34.2) 1-50 n-Pr Me 3, 5-Me2 CO-c-Pr OMe 1-51 n-Pr Me 3, 5-Me2 CH2OMe OMe 1.4979(22.1) 1-52 n-Pr Me 3, 5-Me2 CH2OEt OMe 1.4942 (22.7) 35 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-53 n-Pr Me 3, 5-Me2 COOMe OMe 1.4980(22.7) 1-54 n-Pr Me 3, 5-Me2 COOEt OMe 1.4952(23.0) 1-55 n-Pr Me 3, 5-Me2 COO-n-Pr OMe 1-56 n-Pr Me 3, 5-Me2 COO-i-Bu OMe 1.4933(23.2) 1-57 n-Pr Me 3, 5-Me2 H OEt 178-179 1-58 n-Pr Me 3, 5-Me2 Ac OEt 1-59 n-Pr Me 3, 5-Me2 COEt OEt 1.4980(22.7) 1-60 n-Pr Me 3, 5-Me2 CO-c-Pr OEt 1-61 n-Pr Me 3, 5-Me2 CH2OMe OEt 1-62 n-Pr Me 3, 5-Me2 CH2OEt OEt 1-63 n-Pr Me 3, 5-Me2 COOMe OEt 1-64 n-Pr Me 3, 5-Me2 COOEt OEt 1-65 n-Pr Me 3, 5-Me2 COO-n-Pr OEt 1-66 n-Pr Me 3, 5-Me2 COO-i-Bu OEt 1-67 n-Pr Me 3-CF3-5-Me H H 131-133 1-68 n-Pr Me 3-CF3-5-Me Ac H 1-69 n-Pr Me 3-CF3-5-Me H OMe 124 1-70 n-Pr Me 3-CF3-5-Me Ac OMe 1.4711(25.6) 1-71 n-Pr Me 3-CF3-5-Me COEt OMe 1.4700(26.8) 1-72 n-Pr Me 3-CF3-5-Me CO-c-Pr OMe 1.4795(25.5) 1-73 n-Pr Me 3-CF3-5-Me CH2OMe OMe 1-74 n-Pr Me 3-CF3-5-Me CH2OEt OMe 1.4658(26.9) 1-75 n-Pr Me 3-CF3-5-Me COOMe OMe 126-128 1-76 n-Pr Me 3-CF3-5-Me COOEt OMe 1.4671 (26.9) 1-77 n-Pr Me 3-CF3-5-Me COO-n-Pr OMe 1-78 n-Pr Me 3-CF3-5-Me COO-i-Bu OMe 1.4645(26.9) 1-79 n-Pr Me 3-CF3-5-Me H OEt 1-80 n-Pr Me 3-CF3-5-Me Ac OEt 1-81 n-Pr Me 3-CF3-5-Me COEt OEt 36 Table 1 (continued) No. G Y1 Y2 J- m R1 R2 Property 1-82 n-Pr Me 3-CF3-5-Me CO-c-Pr OEt 1-83 n-Pr Me 3-CF3-5-Me CH20Me OEt 1-84 n-Pr Me 3-CF3-5-Me CH20Et OEt 1-85 n-Pr Me 3-CF3-5-Me COOMe OEt 1-86 n-Pr Me 3-CF3-5-Me COOEt OEt 1-87 n-Pr Me 3-CF3-5-Me COO-n-Pr OEt 1-88 n-Pr Me 3-CF3-5-Me COO-i-Bu OEt 1-89 n-Bu Me 3, 5-Me2 H H 150-151.5 1-90 n-Bu Me 3, 5-Me2 Ac H 1-91 n-Bu Me 3, 5-Me2 H OMe 196-197 1-92 n-Bu Me 3, 5-Me2 Ac OMe 1-93 n-Bu Me 3, 5-Me2 H OEt 1-94 n-Bu Me 3, 5-Me2 Ac OEt 1-95 n-Bu Me 3-CF3-5-Me H H 83-85 1-96 n-Bu Me 3-CF3-5-Me Ac H 1-97 n-Bu Me 3-CF3-5-Me H OMe 1-98 n-Bu Me 3-CF3-5-Me Ac OMe 1-99 n-Bu Me 3-CF3-5-Me H OEt 1-100 n-Bu Me 3-CF3-5-Me Ac OEt 1-101 i-Bu Me 3-Me H H 141-144 1-102 i-Bu Me 3-Me Et OMe 1.4916(23.7) 1-103 i-Bu Me 3-Me Ac OMe 1.4961(26.4) 1-104 i-Bu Me 3-Me COEt OMe 1.4973(26.2) 1-105 i-Bu Me 3-Me CO-c-Pr OMe 1.5014(25.5) 1-106 i-Bu Me 3-Me C0(4-Me-Ph) OMe amorphous 1-107 i-Bu Me 3-Me CO(4-N02-Ph) OMe amorphous 1-108 i-Bu Me 3-Me COOMe OMe 95.5-97.8 1-109 i-Bu Me 3-Me COOEt OMe 84.6-86.2 1-110 i-Bu Me 3-Me COO-n-Pr OMe 86.7-88.4 37 Table 1 (continued) No. G Y1 Y2 J- m R1 R2 Property 1-111 i-Bu Me 3-Me COO-i-Bu OMe 91.8-94.0 1-112 i-Bu Me 3-Me CH2OMe OMe 1.4919(24.0) 1-113 i-Bu Me 3-Me CH2OEt OMe 1.4920(24.4) 1-114 i-Bu Me 3-CF3 H H 172-174 1-115 i-Bu Me 3-CF3 Ac H 1-116 i-Bu Me 3-CF3 H OMe amorphous 1-117 i-Bu Me 3-CF3 Ac OMe 1-118 i-Bu Me 3-CF3 H OEt 1-119 i-Bu Me 3-CF3 Ac OEt 1-120 i-Bu Et 3-CF3 H H 175-176 1-121 i-Bu Me 5-CF3 H H 155-156 1-122 i-Bu Me 5-SMe H H 107-110 1-123 i-Bu Me 3, 5-Me2 H H 148-151 1-124 i-Bu Me 3, 5-Me2 S02(4-F-Ph) H amorphous 1-125 i-Bu Me 3, 5-Me2 Ac H 1.5021(22.5) 1-126 i-Bu Me 3, 5-Me2 COEt H 143.1-148.8 1-127 i-Bu Me 3, 5-Me2 COPh H 51.3-65.3 1-128 i-Bu Me 3, 5-Me2 COCH2CMe3 H 1.4859(22.0) 1-129 i-Bu Me 3, 5-Me2 CH2OEt H 1.4882(23.8) 1-130 i-Bu Me 3, 5-Me2 CH20(CH2)7Me H 1.4854(22.0) 1-131 i-Bu Me 3, 5-Me2 CH20(CH2)2OMe H 1.4889(21.9) 1-132 i-Bu Me 3, 5-Me2 CH2OBn H 1.5212 (21.9) 1-133 i-Bu Me 3, 5-Me2 COOCH2Cl H 121.1-124.8 1-134 i-Bu Me 3, 5-Me2 COOCH2CCl3 H 143.1-145.6 1-135 i-Bu Me 3, 5-Me2 COO(CH2)2CH2Cl H 117.1-121.4 1-136 i-Bu Me 3, 5-Me2 COO-i-Bu H 122.2-138.0 1-137 i-Bu Me 3, 5-Me2 COO-t-Bu H 39.2 1-138 i-Bu Me 3, 5-Me2 COO(CH2)2OMe H 1.4750(23.5) 1-139 i-Bu Me 3, 5-Me2 COO(CH2)15Me H 90.5-92.1 38 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-140 i-Bu Me 3, 5-Me2 Ac OMe 1.5016(23.3) 1-141 i-Bu Me 3/ 5-Me2 COEt OMe 1.4981(23.5) 1-142 i-Bu Me 3, 5-Me2 CO-i-Pr OMe 82.5-83 1-143 i-Bu Me 3, 5-Me2 COPh OMe 1.5219(23.7) 1-144 i-Bu Me 3, 5-Me2 CH2OMe OMe 1.4944(23.1) 1-145 i-Bu Me 3, 5-Me2 CH2OEt OMe 1.4892(22.2) 1-146 i-Bu Me 3/ 5-Me2 CH20(CH2)2OMe OMe 1.4885(25.1) 1-147 i-Bu Me 3, 5-Me2 COOMe OMe 1.4926(23.2) 1-148 i-Bu Me 3, 5-Me2 COOEt OMe 1.4894(23.2) 1-149 i-Bu Me 3, 5-Me2 COOCH2Cl OMe 1.4941(21.5) 1-150 i-Bu Me 3/ 5-Me2 COO-n-Pr OMe 1.4928(22.2) 1-151 i-Bu Me 3, 5-Me2 COO-i-Pr OMe 1.4884(23.0) 1-152 i-Bu Me 3, 5-Me2 COO-i-Bu OMe 1.4829(22.3) 1-153 i-Bu Me 3/ 5-Me2 COOCH2CMe3 OMe 1.4864(23.0) 1-154 i-Bu Me 3, 5-Me2 COO(CH2)2OMe OMe 1.4959(23.0) 1-155 i-Bu Me 3 5-Me2 H OMe 189-190 1-156 i-Bu Me 3 , 5-Me2 Et OMe amorphous 1-157 i-Bu Me 3 , 5-Me2 CH2CC13 OMe 1.4939(22.2) 1-158 i-Bu Me 3 , 5-Me2 Ac OEt 1.4940(26.4) 1-159 i-Bu Me 3 , 5-Me2 COEt OEt 1.4921 (26.5) 1-160 i-Bu Me 3 , 5-Me2 CO-i-Pr OEt paste 1-161 i-Bu Me 3 , 5-Me2 COPh OEt 1-162 i-Bu Me 3 , 5-Me2 CH2OMe OEt 1-163 i-Bu Me 3 , 5-Me2 CH2OEt OEt 1-164 i-Bu Me 3 , 5-Me2 CH20(CH2)2OMe OEt 1-165 i-Bu Me 3 , 5-Me2 COOMe OEt 1-166 i-Bu Me 3 , 5-Me2 COOEt OEt 1-167 i-Bu Me 3 , 5-Me2 COOCH2Cl OEt 1-168 i-Bu Me 3 , 5-Me2 COO-n-Pr OEt 39 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-169 i-Bu Me 3, 5-Me2 COO-i-Pr OEt 1-170 i-Bu Me 3, 5-Me2 COO-i-Bu OEt 1-171 i-Bu Me 3, 5-Me2 COOCH2CMe3 OEt 1-172 i-Bu Me 3, 5-Me2 COO(CH2)2OMe OEt 1-173 i-Bu Me 3, 5-Me2 H OEt 165-166 1-174 i-Bu Me 3, 5-Me2 Et OEt 1-175 i-Bu Me 3, 5-Me2 CH2CC13 OEt 1-176 i-Bu Et 3, 5-Me2 H H 127-128 1-177 i-Bu Me 3, 5-Me2 H F 136.5-137.5 1-178 i-Bu Me 3, 5-Me2 Et H 1.4904(25.7) 1-179 i-Bu Me 3-Me-5-F H H 169.5-171 1-180 i-Bu Me 3-Me-5-F H OMe 135-137 1-181 i-Bu Me 3-Me-5-F Et OMe 1.4825(26.0) 1-182 i-Bu Me 3-Me-5-F Ac OMe 86.4 1-183 i-Bu Me 3-Me-5-F COPh OMe 124.1-130.8 1-184 i-Bu Me 3-Me-5-F COOMe OMe 64.5-80.5 1-185 i-Bu Me 3-Me-5-F COO-i-Bu OMe 1.4789(23.7) 1-186 i-Bu Me 3-Me-5-F COO(CH2)2OMe OMe 1.4857 (22.3) 1-187 i-Bu Me 3-Me-5-F CH2OEt OMe 1.4804 (23.8) 1-188 i-Bu Me 3-Me-5-Cl H H 160-161 1-189 i-Bu Me 3-Me-5-Cl H OMe 144-146 1-190 i-Bu Me 3-Me-5-Cl Me OMe 1.4919(25.6) 1-191 i-Bu Me 3-Me-5-Cl Et OMe 1.4938(26.0) 1-192 i-Bu Me 3-Me-5-Cl CH2OMe OMe 1.4961(26.0) 1-193 i-Bu Me 3-Me-5-Cl CH2OEt OMe 1.4932(25.6) 1-194 i-Bu Me 3-Me-5-Cl COOMe OMe 1.4883(25.6) 1-195 i-Bu Me 3-Me-5-Cl COOEt OMe 1.4915(26.0) 1-196 i-Bu Me 3-Me-5-Cl COO-i-Bu OMe 1.4850(25.6) 1-197 i-Bu Me 3-Me-5-Cl COO(CH2)2OMe OMe 1.4946(26.0) 40 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-198 i-Bu Me 3-Me-5-Cl Ac OMe 102.6-102.8 1-199 i-Bu Me 3-Me-5-Cl COEt OMe 101.8-104.2 1-200 i-Bu Me 3-Me-5-Cl COPh OMe 1.5210(26.0) 1-201 i-Bu Et 3-Me-5-Cl H H 104.5-106 1-202 i-Bu Me 3-Me-5-I H H 152-153 1-203 i-Bu Me 3-Me-5-CF3 H OMe 88-89 1-204 i-Bu Me 3-Me-5-CF3 Ac OMe 1.4710(25.7) 1-205 i-Bu Me 3-Me-5-CF3 COOMe OMe 1.4672(25.7) 1-206 i-Bu Me 3-Me-5-CF3 CH2OEt OMe 1.4652(25.7) 1-207 i-Bu Me 3-CF3-5-Me H H 1.4869(23.4) 1-208 i-Bu Me 3-CF3-5-Me Ac H 152-152.5 1-209 i-Bu Me 3-CF3-5-Me COOMe H 148.5-150 1-210 i-Bu Me 3-CF3-5-Me CH2OEt H 1.4623(22.8) 1-211 i-Bu Me 3-CF3-5-Me H OMe 138-139 1-212 i-Bu Me 3-CF3-5-Me COOMe OMe 1.4729(20.7) 1-213 i-Bu Me 3-CF3-5-Me COOEt OMe 1.4695(20.7) 1-214 i-Bu Me 3-CF3-5-Me COOCH2CH=CH2 OMe 1.4742(24.5) 1-215 i-Bu Me 3-CF3-5-Me COO(CH2)2Me OMe 1.4685(20.7) 1-216 i-Bu Me 3-CF3-5-Me COO(CH2)3Me OMe 1.4689(24.5) 1-217 i-Bu Me 3-CF3-5-Me COO-i-Bu OMe 1.4669(22.6) 1-218 i-Bu Me 3-CF3-5-Me COOPh OMe 50-55 1-219 i-Bu Me 3-CF3-5-Me COO(CH2)2OMe OMe 1.4691(22.3) 1-220 i-Bu Me 3-CF3-5-Me COSMe OMe 1.4870(24.9) 1-221 i-Bu Me 3-CF3-5-Me COSEt OMe 1.4862(24.9) 1-222 i-Bu Me 3-CF3-5-Me CH2OMe OMe 1.4669(22.4) 1-223 i-Bu Me 3-CF3-5-Me CH2OEt OMe 108-110 1-224 i-Bu Me 3-CF3-5-Me Ac OMe 1.4720(20.6) 1-225 i-Bu Me 3-CF3-5-Me CO-c-Pr OMe 1.4735(24.8) 1-226 i-Bu Me 3-CF3-5-Me H OEt 41 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-227 i-Bu Me 3-CF3-5-Me Ac OEt 1-228 i-Bu Me 3-CF3-5-Cl H H 136-137 1-229 i-Bu Me 3-CF3-5-Cl Ac H 1-230 i-Bu Me 3-CF3-5-Cl H OMe 130-132 1-231 i-Bu Me 3-CF3-5-C1 Ac OMe 1-232 i-Bu Me 3-CF3-5-Cl H OEt 1-233 i-Bu Me 3-CF3-5-Cl Ac OEt 1-234 (CH2)4Me Me 3, 5-Me2 H H 128-130 1-235 (CH2)4Me Me 3, 5-Me2 Ac H 1-236 (CH2)4Me Me 3, 5-Me2 H OMe 1-237 (CH2)4Me Me 3, 5-Me2 Ac OMe 1-238 (CH2)4Me Me 3, 5-Me2 H OEt 1-239 (CH2)4Me Me 3, 5-Me2 Ac OEt 1-240 (CH2)4Me Me 3-CF3-5-Me H H 1-241 (CH2)4Me Me 3-CF3-5-Me Ac H 1-242 (CH2)4Me Me 3-CF3-5-Me H OMe 1-243 (CH2)4Me Me 3-CF3-5-Me Ac OMe 1-244 (CH2)4Me Me 3-CF3-5-Me H OEt 1-245 (CH2)4Me Me 3-CF3-5-Me Ac OEt 1-246 CH2CMe3 Me 3, 5-Me2 H H 174-176 1-247 CH2CMe3 Me 3, 5-Me2 Ac H 1-248 CH2CMe3 Me 3, 5-Me2 H OMe 1-249 CH2CMe3 Me 3, 5-Me2 Ac OMe 1-250 CH2CMe3 Me 3, 5-Me2 H OEt 1-251 CH2CMe3 Me 3, 5-Me2 Ac OEt 1-252 CH2CMe3 Me 3-CF3-5-Me H H 1-253 CH2CMe3 Me 3-CF3-5-Me Ac H 1-254 CH2CMe3 Me 3-CF3-5-Me H OMe 1-255 CH2CMe3 Me 3-CF3-5-Me Ac OMe 42 Table 1 (continued) No. G Y1 Y2 R1 R2 Property 1-256 CH2CMe3 Me 3-CF3-5-Me H OEt 1-257 CH2CMe3 Me 3-CF3-5-Me Ac OEt 1-258 CH2CH(Me)Et Me 3, 5-Me2 H H 67-70 1-259 CH2CH(Me)Et Me 3, 5-Me2 Ac H 1-260 CH2CH(Me)Et Me 3, 5-Me2 H OMe 158-160 1-261 CH2CH(Me)Et Me 3, 5-Me2 Ac OMe 1-262 CH2CH(Me)Et Me 3, 5-Me2 H OEt 1-263 CH2CH(Me)Et Me 3, 5-Me2 Ac OEt 1-264 CH2CH(Me)Et Me 3-CF3-5-Me H H 1-265 CH2CH(Me)Et Me 3-CF3-5-Me Ac H 1-266 CH2CH(Me)Et Me 3-CF3-5-Me H OMe 143-144 1-267 CH2CH(Me)Et Me 3-CF3-5-Me Ac OMe 1-268 CH2CH(Me)Et Me 3-CF3-5-Me H OEt 1-269 CH2CH(Me)Et Me 3-CF3-5-Me Ac OEt 1-270 CH2CHEt2 Me 3, 5-Me2 H H 67-70 1-271 CH2CHEt2 Me 3, 5-Me2 Ac H 1-272 CH2CHEt2 Me 3, 5-Me2 H OMe 1-273 CH2CHEt2 Me 3, 5-Me2 Ac OMe 1-274 CH2CHEt2 Me 3, 5-Me2 H OEt 1-275 CH2CHEt2 Me 3, 5-Me2 Ac OEt 1-276 CH2CHEt2 Me 3-CF3-5-Me H H 1-277 CH2CHEt2 Me 3-CF3-5-Me Ac H 1-278 CH2CHEt2 Me 3-CF3-5-Me H OMe 1-279 CH2CHEt2 Me 3-CF3-5-Me Ac OMe 1-280 CH2CHEt2 Me 3-CF3-5-Me H OEt 1-281 CH2CHEt2 Me 3-CF3-5-Me Ac OEt 1-282 (CH2)2CHMe2 Me 3, 5-Me2 H H 152-153 1-283 (CH2)2CHMe2 Me 3, 5-Me2 Ac H 1-284 (CH2)2CHMe2 Me 3, 5-Me2 H OMe 166-167 43 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-285 (CH2)2CHMe2 Me 3, 5-Me2 Ac OMe 1.4925(21.8) 1-286 (CH2)2CHMe2 Me 3, 5-Me2 H OEt 1-287 (CH2)2CHMe2 Me 3, 5-Me2 Ac OEt 1-288 (CH2)2CHMe2 Me 3-CF3-5-Me H H 1-289 (CH2)2CHMe2 Me 3-CF3-5-Me Ac H 1-290 (CH2)2CHMe2 Me 3-CF3-5-Me H OMe 138-140 1-291 (CH2)2CHMe2 Me 3-CF3-5-Me Ac OMe 1-292 (CH2)2CHMe2 Me 3-CF3-5-Me H OEt 1-293 (CH2)2CHMe2 Me 3-CF3-5-Me Ac OEt 1-294 (CH2)7Me Me 3, 5-Me2 H H 1.5052 (23.3) 1-295 (CH2)7Me Me 3, 5-Me2 Ac H 1-296 (CH2)7Me Me 3, 5-Me2 H OMe 1-297 (CH2)7Me Me 3, 5-Me2 Ac OMe 1-298 (CH2)7Me Me 3, 5-Me2 H OEt 1-299 (CH2)7Me Me 3, 5-Me2 Ac OEt 1-300 (CH2)7Me Me 3-CF3-5-Me H H 1-301 (CH2)7Me Me 3-CF3-5-Me Ac H 1-302 (CH2)7Me Me 3-CF3-5-Me H OMe 1-303 (CH2)7Me Me 3-CF3-5-Me Ac OMe 1-304 (CH2)7Me Me 3-CF3-5-Me H OEt 1-305 (CH2)7Me Me 3-CF3-5-Me Ac OEt 1-306 n-Pr Me 3-Me-5-CF3 H H 141-143 1-307 n-Pr Me 3-Me-5-CF3 H OMe 152-153 1-308 n-Pr Me 3-Me-5-CF3 Ac OMe 1.4688(25.6) 1-309 n-Pr Me 3-Me-5-CF3 Ac H 112-113 1-310 i-Bu Me 3-CF3-5-Me CH2OMe H 1.4690(25.9) 44 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-311 i-Bu Me 3-Me-5-F COOCH2CH2Cl OMe 1.4966(24.7) 1-312 i-Bu Me 3, 5-Me2 COOCH2CH2Cl OMe 1.5039(24.8) 1-313 i-Bu Me 3, 5-Me2 COCH2CMe3 OMe 1.4914(24.8) 1-314 i-Bu Me 3, 5-Me2 CO-c-Pr OMe 1.5061(24.9) 1-315 i-Bu Me 3-CF3-5-Me COEt H 171-173 1-316 i-Bu CI CH2CH2 3, 5-Me2 H OMe 170-171 1-317 i-Bu CI CH2CH2 3, 5-Me2 AC OMe 1.4955(24.8) 1-318 i-Bu Me 3, 5-Me2 CO-n-Pr OMe 1.4943(24.8) 1-319 i-Bu Me 3, 5-Me2 CO-t-Bu OMe 113-115 1-320 i-Bu Me 3, 5-Me2 CO(4-MeO-Ph) OMe 1.5198(25.3) 1-321 i-Bu Me 3, 5-Me2 CO(4-Me-Ph) OMe 1.5139(25.0) 1-322 i-Bu Me 3, 5-Me2 CO(4-Cl-Ph) OMe 51-64 1-323 n-Pr Me 3-Me-5-CF3 COEt OMe 1.4705(26.8) 1-324 i-Bu Me 3, 5-Me2 CO(3-Cl-Ph) OMe 1.5266(25.4) 1-325 i-Bu Me 3, 5-Me2 CO(3-Me-Ph) OMe 1.5182(25.5) 1-326 i-Bu Me 3, 5-Me2 CO(3-MeO-Ph) OMe 1.5165(26.5) 1-327 i-Bu Me 3, 5-Me2 CO(2-Me-Ph) OMe 88-128 1-328 i-Bu Me 3, 5-Me2 CO(2-Cl-Ph) OMe 121-122 1-329 i-Bu Me 3, 5-Me2 CO(2-MeO-Ph) OMe 57-83 1-330 i-Bu Me 3, 5-Me2 COCH=CH2 OMe 1.5088(24.5) 1-331 i-Bu Me 3, 5-Mez COCHClMe OMe amorphous 1-332 i-Bu Me 3, 5-Me2 CO(3-Me-2-Pyr) OMe 52-64 1-333 i-Bu Me 3, 5-Me2 SNEt2 OMe 1-334 i-Bu Me 3-CF3-5-Me CO-i-Pr H 161-163 1-335 Et Me 3-CF3-5-Me CO-i-Pr OMe 1.4680(26.4) 1-336 i-Bu Me 3, 5-Me2 CO-t-Pen OMe 95-96 45 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-337 i-Bu Me 3, 5-Me2 COCH2OMe OMe 1.4939(26.5) 1-338 i-Bu Me 3, 5-Me2 CO(4-CF3-Ph) OMe 54 1-339 i-Bu Me 3, 5-Me2 COCH2Ph OMe 1-340 i-Bu Me 3, 5-Me2 COCH=CMe2 OMe 1.5091(26.5) 1-341 i-Bu Me 3, 5-Me2 COCH=CHMe OMe 1.5082(26.5) 1-342 i-Bu Me 3, 5-Me2 COCH2CH2COOEt OMe 100-101 1-343 n-Pr Me 3-CF3-5-Me COOCH2CH=CH2 OMe 1.4728(27.0) 1-344 n-Pr Me 3-CF3-5-Me CO-t-Bu OMe 1.4715(26.9) 1-345 n-Pr Me 3-CF3-5-Me CO-n-Pr OMe 1.4660(26.8) 1-346 Et Me 3-CF3-5-Me COOCH2CH2OMe OMe 1.4695(26.2) 1-347 Et Me 3-CF3-5-Me CO-t-Bu OMe 1.4730(26.2) 1-348 i-Bu Me 3, 5-Me2 COCMe2CH2Cl OMe 1.5062(26.7) 1-349 i-Bu Me 3, 5-Me2 CO-c-Pen OMe 1.5019(26.8) 1-350 i-Bu CH=CH2 3, 5-Me2 H OMe 124-130 1-351 i-Bu CH=CH2 3, 5-Me2 CO-i-Pr OMe 1.5044(25.8) 1-352 i-Bu Me 3, 5-Me2 CO(2,4-Cl2-Ph) OMe 1.5220(26.1) 1-353 i-Bu Me 3, 5-Me2 CO(3,4-Cl2-Ph) OMe 53 1-354 n-Pr Me 3, 5-Me2 CO-i-Pr OMe 1.5075(25.1) 1-355 n-Pr Me 3-CF3-5-Me CO-i-Pr OMe 1.4741(25.8) 1-356 Et Me 3-CF3-5-Me COOCH2CH=CH2 OMe 1.4781 (25.9) 1-357 n-Pr Me 3, 5-Me2 CO-t-Bu OMe 1.4888(26.0) 1-358 n-Pr Me 3, 5-Me2 CO(4-Cl-Ph) OMe 41 1-359 Et Me 3, 5-Me2 n-Pen OMe 1.4897 (25.0) 1-360 Et Me 3, 5-Me2 CH2(4-F-Ph) OMe 107.9 1-361 Et Me 3, 5-Me2 CO-c-Bu OMe 1.4939(32.1) 1-362 Et Me 3, 5-Me2 CO-i-Pr OMe 100.3-103.4 1-363 Et Me 3, 5-Me2 CO-s-Bu OMe 1.5031(22.9) 46 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-364 Et Me 3, 5-Me2 CO-t-Bu OMe 108 1-365 Et Me 3, 5-Me2 COCMe2Et OMe 1.4983(20.5) 1-366 Et Me 3, 5-Me2 COCH2OMe OMe 1.4958(21.6) 1-367 Et Me 3, 5-Me2 COCHEt2 OMe 1.4991(21.8) 1-368 Et Me 3, 5-Me2 CO-c-Pen OMe 1.4977(30.5) 1-369 Et Me 3, 5-Me2 CO-c-Hex OMe 1.4934(25.2) 1-370 Et Me 3, 5-Me2 COCH2OPh OMe amorphous 1-371 Et Me 3, 5-Me2 COCH2-t-Bu OMe 1.4962(32.1) 1-372 Et Me 3, 5-Me2 CO(4-CF3-Ph) OMe 1.5023(32.2) 1-373 Et Me 3, 5-Me2 corph OMe 1.4211(32.0) 1-374 Et Me 3, 5-Me2 CH2OCH2CH2OMe OMe 1.4892(31.0) 1-375 Et Me 3, 5-Me2 CH20-i-Pr OMe 1.4855(30.2) 1-376 Et Me 3, 5-Me2 CH20-i-Bu OMe 1.4849(33.2) 1-377 Et Me 3, 5-Me2 CH20-n-Pr OMe 1.4982(23.1) 1-378 Et Me 3, 5-Me2 CH20-n-Bu OMe 1.4940(23.2) 1-379 Et Me 3, 5-Me2 C00CH2CC13 OMe 145.2-145.8 1-380 Et Me 3, 5-Me2 COO-n-Pen OMe 1.4960(20.2) 1-381 Et Me 3-CF3-5-Me COEt H 127-128 1-382 Et Me 3-CF3-5-Me CO-c-Bu OMe 1.4818(19.1) 1-383 Et Me 3-CF3-5-Me CO-s-Bu OMe 1.4701(24.4) 1-384 Et Me 3-CF3-5-Me COCHEt2 OMe 1.4724(24.3) 1-385 Et Me 3-CF3-5-Me CH20-n-Bu OMe 1.4670(23.7) 1-386 Et Me 3-CF3-5-Me CH20-i-Bu OMe 1.4659(21.8) 1-387 Et Me 3-CF3-5-Me CH20-n-Pr OMe 1.4672(21.8) 1-388 Et Me 3-Me-5-Cl H OMe 127.3-128.5 1-389 Et Me 3-Me-5-Cl CO-i-Pr OMe 134.1-135.4 47 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-390 Et Me 3-Me-5-Cl CO-c-Bu OMe 136.1-137.2 1-391 Et Me 3-Me-5-Cl CO-t-Bu OMe 108.6-110.4 1-392 Et Me 3-Me-5-Cl COO-i-Bu OMe 1.4931(32.1) 1-393 Et Me 3-Me-5-Cl CH20-i-Pr OMe 1.4884 (30.5) 1-394 Et Me 3-Me-5-Cl CH20-n-Bu OMe 1.4875(29.1) 1-395 Et Me 3-Me H OMe 183.8-185.4 1-396 Et Me 3-Me CO-i-Pr OMe 114.4-114.9 1-397 Et Me 3-Me CO-c-Pen OMe 1.4975(31.0) 1-398 Et Me 3-Me CH20-i-Pr OMe 1.4902(23.4) 1-399 Et Me 3, 5-Me2 CO-n-Pr OEt 1.4932 (23.0) 1-400 Et Me 3, 5-Me2 CO-i-Pr OEt 80-81 1-401 n-Pr Me 3, 5-Me2 COOCH2CH=CH2 OMe 1.4841 (23.7) 1-402 n-Pr Me 3, 5-Me2 COOCH2CHEt-n-Bu OMe 1.4894 (23.8) 1-403 n-Pr Me 3, 5-Me2 COCH2OMe OMe paste 1-404 n-Pr Me 3, 5-Me2 Me OMe 1.4983(22.0) 1-405 n-Pr Me 3, 5-Me2 Et OMe 1.4970(20.0) 1-406 n-Pr Me 3, 5-Me2 CH2CH=CH2 OMe 1.5019(23.2) 1-407 n-Pr Me 3, 5-Me2 (CH2)7 Me OMe 1.4880(23.5) 1-408 n-Pr Me 3-CF3-5-Me COOMe H 140-145 1-409 n-Pr Me 3-CF3-5-Me COOEt H 129-130 1-410 n-Pr Me 3-CF3-5-Me COEt H 140-145 1-411 n-Pr Me 3-CF3-5-Me CO-i-Pr H 135-137 1-412 n-Pr Me 3-CF3-5-Me CH20-n-Pr OMe 1.4673(21.8) 1-413 n-Pr Me 3-CF3-5-Me CH20-t-Bu OMe 1.4669(21.7) 1-414 i-Bu Me 3, 5-Me2 Me OMe paste 1-415 i-Bu Me 3, 5-Me2 n-Pr OMe paste 48 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-416 i-Bu Me 3/ 5-Me2 CH2CH=CH2 OMe 70-71 1-417 i-Bu Me 3/ 5-Me 2 CH2(4-N02-Ph) OMe paste 1-418 i-Bu Me 3/ 5-Me2 CH2Ph OMe 90-97 1-419 i-Bu Me 3/ 5-Me2 CH2(4-Me-Ph) OMe paste 1-420 i-Bu Me 3/ 5-Me2 CH20-n-Pr OMe 59-65 1-421 i-Bu Me 3, 5-Me2 CH20-n-Bu OMe paste 1-422 i-Bu Me 3/ 5-Me2 CH20-i-Pr OMe paste 1-423 i-Bu Me 3; 5-Me2 CH20-i-Bu OMe 80-82 1-424 i-Bu Me 3; 5-Me2 CH20-t-Bu OMe paste 1-425 i-Bu Me 3/ 5-Me2 CH20-s-Bu OMe paste 1-426 i-Bu Me 3, 5-Me2 CH2OCH2CF3 OMe paste 1-427 i-Bu Me 3 5-Me2 CH2OCH2CH=CH2 OMe paste 1-428 i-Bu Me 3 , 5-Me2 CH20(CH2)7Me OMe paste 1-429 i-Bu Me 3 , 5-Me2 CO-c-Bu OMe paste 1-430 i-Bu Me 3 , 5-Me2 CO-s-Bu OMe 106.1-107.8 1-431 i-Bu Me 3 5-Me2 COCHEt2 OMe 97.2-101.8 1-432 i-Bu Me 3 , 5-Me2 COCMe2Br OMe 93-106 1-433 i-Bu Me 3 , 5-Me2 CO-c-Hex OMe 1.5035(24.7) 1-434 i-Bu Me 3 , 5-Me2 CH2(2, 4, 6- Cl3-Ph) OMe 64.2-66.7 1-435 i-Bu Me 3 , 5-Me2 ccT^ OMe 1.4991 (20.5) 1-436 i-Bu Me 3 , 5-Me2 COCHMeOMe OMe 1.4977(20.6) 1-437 i-Bu Me 3 , 5-Me2 COCMe2OMe OMe 1.4906(23.6) 1-438 i-Bu Me 3 , 5-Me2 COOPh OMe 135.3-136.1 1-439 i-Bu Me 3-] Vte-5-CF3 COO-i-Bu OMe 1.4733(21.2) 1-440 i-Bu Me 3-] ^e-5-CF3 CO-t-Bu OMe 1.4745(21.2) 1-441 i-Bu Me 3-] ^e-5-CF3 CO-i-Pr OMe 1.4722(32.1) 49 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-442 i-Bu Me 3-Me-5-CF3 CO-c-Pr OMe 1.4780 (32.0) 1-443 i-Bu Me 3-CF3-5-Me COEt OMe 1.4727 (24.1) 1-444 i-Bu Me 3-CF3-5-Me CO-i-Pr OMe 1.4720(24.2) 1-445 i-Bu Me 3-CF3-5-Me CH20-n-Pr OMe 1.4658 (22.7) 1-446 i-Bu Me 3-CF3-5-Me CH20-n-Bu OMe 1.4670(22.5) 1-447 i-Bu Me 3-CF3-5-Me CH20-i-Bu OMe 1.4625(21.9) 1-448 i-Bu Me 3-Me-5-F CO-t-Bu OMe amorphous 1-449 i-Bu Me 3-Me-5-Cl CO-i-Pr OMe 124-124.4 1-450 i-Bu Me 3-Me-5-Cl CO-t-Bu OMe 1.4860(31.4) 1-451 i-Bu Me 3-Me-5-Cl CO-c-Bu OMe 114-115.3 1-452 i-Bu Me 3-Me-5-Cl COCH2OMe OMe amorphous 1-453 i-Bu Me 3-Me-5-Cl CO-c-Pen OMe 136.2-137 1-454 i-Bu Me 3-Me-5-Cl CH20-n-Pr OMe 1.4887(31.6) 1-455 i-Bu Me 3-Me-5-Cl CH20-i-Bu OMe 60.7-64.7 1-456 i-Bu Me 3-Me CO-i-Pr OMe 67.3-68.2 1-457 i-Bu Me 3-Me CO-t-Bu OMe 124.1-125.5 1-458 i-Bu Me 3-Me CO-s-Bu OMe 1.4914(32.0) 1-459 i-Bu Me 3-Me CO-c-Bu OMe 83-88.6 1-460 i-Bu Me 3-Me CO-c-Pen OMe 1.4990(31.7) 1-461 i-Bu Me 3-Me COCHEt2 OMe 1.4905(28.5) 1-462 i-Bu Me 3-Me CH20-i-Pr OMe 1.4817 (31.7) 1-463 i-Bu H 3, 5-Me2 H OMe 82.8-90.5 1-464 i-Bu Et 3, 5-Me2 H OMe 162-163 1-465 i-Bu CH2CF3 3, 5-Me2 H OMe 176-177 1-466 i-Bu Me 3, 5-Me2 CO-i-Pr F 1.4860(22.7) 1-467 CH2CHMeEt Me 3, 5-Me2 COEt OMe 1.4929(20.1) 1-468 CH2CHMeEt Me 3, 5-Me2 CO-i-Pr OMe 1.4910(20.0) 50 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-469 n-Bu Me 3, 5-Me2 COEt OMe 1.4895(20.6) 1-470 n-Bu Me 3, 5-Me2 CO-i-Pr OMe 1.4835(18.9) 1-471 CH2CH-c-Pen Me 3-CF3-5-Me H H 200-201 1-472 CH2CH2CHMe2 Me 3, 5-Me2 COEt OMe 1.4960(20.5) 1-473 CH2CH2CHMe2 Me 3, 5-Me2 CO-i-Pr OMe 1.4950(21.6) 1-474 Et i-Pr 3, 5-Me2 H OEt 173-174 1-475 Et i-Pr 3, 5-Me2 Ac OEt 88-89 1-476 Et Me 3, 5-Me2 H O-n-Pr 104-105 1-477 Et Me 3, 5-Me2 CO-n-Pr O-n-Pr 1.4833(33.0) 1-478 Et Me 3, 5-Me2 CO-i-Pr O-n-Pr 1.4919(33.0) 1-479 Et Me 3, 5-Me2 CO-t-Bu O-n-Pr 1.4848(32.0) 1-480 Et Me 3, 5-Me2 CH2OEt O-n-Pr 1.4729(23.5) 1-481 Et Me 3-I-5-Me H H 134-135 1-482 Et Me 3, 5-Me2 COCHMeCOEt OEt 1-483 n-Pr Me 3, 5-Me2 CO-n-Pr OMe 1.4959(31.2) 1-484 n-Pr Me 3, 5-Me2 CO-s-Bu OMe 1.4960(32.3) 1-485 n-Pr Me 3, 5-Me2 CO-c-Pen OMe 1.4880(29.0) 1-486 n-Pr Me 3, 5-Me2 CH20-n-Pr OMe 1.4869(28.0) 1-487 n-Pr Me 3, 5-Me2 CH20-i-Pr OMe 1.4819(29.3) 1-488 n-Pr Me 3-Me-5-Cl H OMe 135.4-139.0 1-489 n-Pr Me 3-Me-5-Cl CO-i-Pr OMe 128.1-128.2 1-490 n-Pr Me 3-Me-5-Cl CO-s-Bu OMe 99.2-99.7 1-491 n-Pr Me 3-Me-5-Cl CO-c-Pr OMe 123.0-123.9 1-492 n-Pr Me 3-Me 5-C1 CO-c-Pen OMe 141.7-142.1 1-493 n-Pr Me 3-Me-5-Cl CH2OEt OMe 1.4954(20.7) 1-494 n-Pr Me 3-I-5-Me H H 183-185 1-495 n-Pr Me 3-Me H OMe 146.8-147.0 51 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-496 n-Pr Me 3-Me CO-i-Pr OMe 61.6-62.9 1-497 n-Pr Me 3-Me CO-s-Bu OMe 1.4960(22.2) 1-498 n-Pr Me 3-Me CO-c-Pen OMe 1.4991(22.1) 1-499 n-Pr Me 3-Me CH20-n-Pr OMe 1.4864(22.8) 1-500 n-Pr Me 3-Me CH20-i-Pr OMe 1.4863(22.4) 1-501 n-Pr Me 3, 5-Me2 CO-n-Pr OEt 1.4892(22.7) 1-502 n-Pr Me 3, 5-Me2 CO-i-Pr OEt 1.4910(22.8) 1-503 n-Pr Me 3, 5-Me2 H O-n-Pr 158-159.5 1-504 n-Pr Me 3, 5-Me2 COEt O-n-Pr 1.4975(20.5) 1-505 n-Pr Me 3, 5-Me2 CO-n-Pr O-n-Pr 1.4940(20.5) 1-506 n-Pr Me 3, 5-Me2 CO-i-Pr O-n-Pr 1.4960(20.6) 1-507 i-Bu CH2CF3 3, 5-Me2 COEt OMe 137-138 1-508 i-Bu CH2CF3 3, 5-Me2 CO-i-Pr OMe 1-509 i-Bu i-Pr 3, 5-Me2 H OMe 166-167 1-510 i-Bu i-Pr 3, 5-Me2 CO-i-Pr OMe 107-108 1-511 i-Bu Me 3-Me-5-Cl H F 143.2-144.7 1-512 i-Bu Me 3-Me-5-Cl CO-i-Pr F 1.4888(23.0) 1-513 i-Bu Me 3-Cl-5-Me H OMe 153-161 1-514 i-Bu Me 3-Cl-5-Me CO-i-Pr OMe paste 1-515 i-Bu Me 3-Cl-5-Me CH20-i-Pr OMe paste 1-516 i-Bu Me 3-Cl-5-Me COOMe OMe amorphous 1-517 i-Bu Me 3-Br-5-Me H OMe 172-174 1-518 i-Bu Me 3-Br-5-Me CO-i-Pr OMe paste 1-519 i-Bu Me 3-Br-5-Me CH20-i-Pr OMe paste 1-520 i-Bu Me 3-I-5-Me H H 178-183 1-521 i-Bu Me 3-Br-5-Me COOMe OMe paste 1-522 i-Bu Me 3-I-5-Me H OMe amorphous 52 Table 1 (continued) No. G Y1 Y2 R1 R2 Property 1-523 i-Bu Me 3-I-5-Me COOMe OMe paste 1-524 i-Bu Me 3-I-5-Me CO-i-Pr OMe paste 1-525 i-Bu Me 3-I-5-Me CH2OEt OMe 100-103 1-526 i-Bu Me 3-I-5-Me CH20-i-Pr OMe 100-102 1-527 i-Bu Me 3, 5-Me2 CH2CH=CMe2 OMe 81-83 1-528 CH=CMe2 Me 3, 5-Me2 H OMe 1-529 i-Bu Me 5-CF3 H OMe 170 1-530 i-Bu Me 5-CF3 CO-i-Pr OMe 1.4680(22.8) 1-531 i-Bu Et 3, 5-Me2 CO-i-Pr OMe 1.4913(23.0) 1-532 CH=CMe2 Me 3, 5-Me2 CO-i-Pr OMe 1-533 i-Bu Me 3, 5-Me2 CO-n-Pr OEt 1.4870(22.5) 1-534 i-Bu Me 3, 5-Me2 H O-n-Pr 138-139 1-535 i-Bu Me 3-1 H OMe 210-218 1-536 i-Bu Me 3-Br H OMe 203 1-537 i-Bu Me 3-C1 H OMe 174-182 1-538 i-Bu Me 3, 5-CI2 H OMe 132 1-539 i-Bu Me 3-1 CO-i-Pr OMe paste 1-540 i-Bu Me 3-Br CO-i-Pr OMe paste 1-541 i-Bu Me 3-C1 CO-i-Pr OMe paste 1-542 i-Bu Me 3-CF3 CO-i-Pr OMe paste 1-543 i-Bu Me 3, 5-CI2 CO-i-Pr OMe 113-114 1-544 i-Bu Me 3, 5-Me2 Me Me F amorphous 1-545 i-Bu Me 3, 5-Me2 Mex> OC s F amorphous 53 Table 1 (continued) No. G Y1 Y2 1 m R1 R2 Property 1-546 i-Bu Me 3, 5-Me2 Me\^N J>-Me OC s OMe 150.4-151.2 1-547 i-Bu Me 3, 5-Me2 CH20Ac OMe 94-95 1-548 i-Bu Me 3, 5-Me2 CH2OC(=0)Et OMe 99 1-549 i-Bu Me 3, 5-Me2 CH20C(=0)-i-Pr OMe 112 1-550 i-Bu Me 3, 5-Me2 COSMe OMe 1-551 i-Bu Me 3, 5-Me2 COSEt OMe 54 Table 2 (Y^Me) No. G Xn Y2 1 m R1 R2 Property 2-1 Et 6-Me 3, 5-Me2 H H 2-2 Et 6-Me 3, 5-Me2 Ac H 2-3 Et 6-Me 3, 5-Me2 H OMe 2-4 Et 6-Me 3, 5-Me2 Ac OMe 2-5 Et 6-Me 3, 5-Me2 H OEt 2-6 Et 6-Me 3, 5-Me2 Ac OEt 2-7 Et 6-Me 3-CF3-5-Me H H 2-8 Et 6-Me 3-CF3-5-Me Ac H 2-9 Et 6-Me 3-CF3-5-Me H OMe 2-10 Et 6-Me 3-CF3-5-Me Ac OMe 2-11 Et 6-Me 3-CF3-5-Me H OEt 2-12 Et 6-Me 3-CF3-5-Me Ac OEt 2-13 n-Pr 6-Me 3, 5-Me2 H H 128-131 2-14 n-Pr 6-Me 3, 5-Me2 Ac H 2-15 n-Pr 6-Me 3, 5-Me2 H OMe 132-134 2-16 n-Pr 6-Me 3, 5-Me2 Ac OMe 1.4905(25.9) 2-17 n-Pr 6-Me 3, 5-Me2 H OEt 154-155 2-18 n-Pr 6-Me 3, 5-Me2 Ac OEt 2-19 n-Pr 6-Me 3-CF3-5-Me H H 2-20 n-Pr 6-Me 3-CF3-5-Me Ac H 2-21 n-Pr 6-Me 3-CF3-5-Me H OMe 104-106 55 Table 2 (continued) No. G Xn Y2 1 m R1 R2 Property 2-22 n-Pr 6-Me 3-CF3-5-Me Ac OMe 1.4751(26.7) 2-23 n-Pr 6-Me 3-CF3-5-Me H OEt 152-153 2-24 n-Pr 6-Me 3-CF3-5-Me Ac OEt 2-25 n-Pr 6-Me 3-Me-5-Cl H OMe 127-128.5 2-26 n-Pr 6-Me 3-CF3-5-Me COEt OMe 151-152 2-27 i-Bu 6-C1 3, 5-Me2 H OMe 106-109 2-28 i-Bu 6-C1 3, 5-Me2 Ac OMe amorphous 2-29 Et 6-Me 3, 5-Me2 CO-c-Pr OMe 138-140 2-30 Et 6-Me 3, 5-Me2 COEt OMe 132-134 2-31 Et 6-Me 3-CF3-5-Me CO-n-Pr OMe 1.4960(26.6) 2-32 n-Pr 6-Me 3-CF3-5-Me COOMe OMe 165-166 2-33 i-Bu 6-Me 3, 5-Me2 H OMe 126-127 2-34 n-Pr 6-Me 3, 5-Me2 CO-i-Pr OMe 1.4955(33.5) 2-35 n-Pr 6-Me 3, 5-Me2 CO-t-Bu OMe 128.5-130.2 2-36 n-Pr 6-Me 3, 5-Me2 COCHEt2 OMe 1.4918(32.6) 2-37 n-Pr 6-Me 3, 5-Me2 COO-i-Bu OMe 1.4870(30.1) 2-38 i-Bu 6-Me 3, 5-Me2 COEt OMe amorphous 2-39 Et 6-Me 3, 5-Me2 CO-i-Pr OMe 1.4952(32.0) 2-40 n-Pr 6-Me 3-Me H OMe amorphous 2-41 n-Pr 6-Me 3-Me CO-i-Pr OMe paste 2-42 n-Pr 6-Me 3, 5-Me2 CO-i-Pr OEt 111-112 2-43 i-Bu 6-Me 3, 5-Me2 CO-i-Pr OMe 38-42 2-44 n-Pr 6-Me 3-CF3-5-Me CO-i-Pr OMe 155 2-45 i-Bu 6-Me 3-CF3-5-Me H OMe 68-70 2-46 n-Pr 6-Me 3, 5-Me2 H OH 192-195 56 Table 3 (R1=H) No G Xn R2 ^-NMRtCDCla/TMS, 5 value (ppm) ] 7.09(s, 1H), 6.54(s, 1H) , 3.76(bs, 3-1 n-Pr 6-Me F 2H) , 2.63(m, 2H) , 2.13 (s, 3H) , 1.58(111, 2H) , 0.96(t, 3H) 7.18(s, 1H), 6.54(s, 1H) , 4.45- 3-2 n-Pr 6-Me H 4.20(br, 2H), 4.27 (m, 1H), 2.50(dd, 2H) , 2.14(s, 3H) , 1.57(111, 2H) , 0.98(t, 3H) 7.10(s, 1H), 6.66(s, 1H), 3.72(bs, 3-3 n-Pr 6-Me OMe 2H), 3.42(s, 3H), 2.84(m, 2H), 2.14(s, 3H), 1.61(m, 2H), 1.00 (t, 3H) 7.09(s, 1H), 6.56(s, 1H), 3.78(bs, 3-4 Et 6-Me F 2H) , 2.71(m, 2H), 2.14 (s, 3H), 1.19(td, 3H) 7.10(s, 1H), 6.68(s, 1H), 3.75(bs, 3-5 Et 6-Me OMe 2H), 3.41 (s, 3H), 2.91(dd, 2H), 2.15(s, 3H), 1.22(t, 3H) 7.22(d, 1H), 6.67(d, 1H), 6.52(dd, 3-6 Et H O-n-Pr 1H), 3.80(br, 2H), 3.46(t, 2H), 2.92(dd, 2H) , 1.69(dd, 2H) , 1.21(t, 3H), 0.94(t, 3H) 7.22(d, 1H), 6.66(d, 1H), 6.51(dd, 3-7 n-Pr H O-n-Pr 1H), 3.78(br, 2H), 3.47 (t, 2H), 2.85(m, 2H), 1.70(dd, 2H) , 1.60(m, 2H), 1.00 (t, 3H), 0.94(t, 3H) 7.24(d, 1H), 6.70(d, 1H), 6.53(dd, 3-8 i-Bu H O-n-Pr 1H), 3.79(bs, 2H), 3.47(t, 2H), 2.81(d, 2H), 2.10(m, 1H) , 1.70(m, 2H), 0.95(t, 3H), 0.91(d, 6H) 57 Table 4 No Y1 Y2m melting point (°C) 4-1 Me 3-Me-5-CF3 124-125.5 58 Table 5 No. ^-NMRtCDCWTMS, 5 value (ppm) ] 7.61(d, 2H) , 7.52(d, 1H), 7.17(m, 4H), 7.11(m, 1H), 1-106 3.69(s, 3H) , 3.47(s, 3H), 2.86(d, 2H), 2.39(s, 3H), 2.37(s, 3H), 1.96(m, 1H), 0.73(d, 6H) 8.27(d, 2H), 7.83(d, 2H), 7.59(d, 1H), 7.22(d, 1H), 1-107 7.17(m, 1H), 6.97(s, 1H), 3.66(s, 3H), 3.51(s, 3H), 2.91(d, 2H) , 2.36(s, 3H), 1.97 (in, 1H) , 0.77 (d, 6H) 8.04(s, 1H), 7.73(br r 1H) , 7.72(d, 1H), 7.50(d, 1H), 1-116 7.43(dc i, 1H) , 4.01(s r 3H) , 3.47(s, 3H), 2.93(d, 2H), 2.21(m, 1H), 0.94(d, 6H) 7.80 (dc i, 2H) , 7.49(d r 1H) , 7.13(dd, 2H), 7.02(dd, 1H), 1-124 6.89(d, 1H), 4.40-4.. 31 (m, 1H), 3.57(s, 3H), 2.42(d, 2H), 2.28(s, 3H) , 2.22(s, 3H) , 1.70-1.59(m, 1H), 0.78(d, 6H) 7.41(d, 1H), 7.01(dd r 1H) , 6.96(d, 1H), 3.98(dd, 2H), 1-156 3.56 (s, 3H), 3.44(s, 3H) , 2.79(d, 2H), 2.06(s, 3H), 2.00(s, 3H) , 1.86(m, 1H), 1.25(dd, 3H), 0.74(d, 6H) 7.47(d, 1H) , 7.16-7. D5(m, 2H), 3.67(s, 3H) , 3.60(dd, 1-160 2H), 3 04 (m, 1H) , 2. 38 (d, 2H) , 2.37(s, 3H) , 2.25(s, 3H) , 1.97(111, 1H), 1.31(t, 3H) , 1.26(d, 6H), 0.77(d, 6H) 7.48(d, 1H), 7.10(d, 1H), 7.08(s, 1H), 5.11(q, 1H), 1-331 3.64 (s, 2.31(s; 3H) 3H) 3.45(s, 2.24(s, 3H) , 3H) , 2.96(dd, 1H), 2.74(dd, 1H), 1.92(m, 1H), 1.77(d, 3H), 0.84(d, 3H) 0.65(d, 3H) 7.41(d, 1H) 7.28(m, 2H) , 7.08(d, 1H), 6.98(m, 2H), 1-370 6.84(m, 2H) 4.98(s, 2H) , 3.63(s, 3H), 3.40(s, 3H), 2.96(q# 2H) 2.18(s, 3H) , 2.14(s, 3H), 1.26(t, 3H) 7.43(d, 1H) r 7.14(d, 1H), 7.18(m, 1H) , 4.32(s, 2H) , 1-403 3.66(s, 3H) , 3.43(s, 3H) , 3.39(s, 3H) , 2.92(m, 2H) , 2.31 (s, 3H) , 2.23(s, 3H) , 1.51(m, 2H), 0.94(t, 3H) 7.41(d, 1H) , 7.01(m, 2H) , 3.58(s, 3H), 3.48(s, 3H), 1-414 3.44(s, 3H) , 2.79(d, 2H) , 2.06(s, 3H), 2.00(s, 3H), 1.85(111, 1H) , 0.76{d, 6H) 7.39(d 1H) , 7.00(dd / 1H) , 6.97(d, 1H), 3.88 (m, 2H), 1-415 3. 56 (s 2.00(s 0.75(d r 3H) r 3H) 6H) , 3.44(s, , 1.84 (m, 3H), 1H), 2.78(d, 2H), 2.05(s, 3H), 1.66(m, 2H), 0.95(t, 3H), 8.18(d , 2H) , 7.50(d, 2H), 7.38(d, 1H), 6.95(dd, 1H) , 1-417 6.88(d 2.73(d r 1H) , 2H) , 5.22(s, , 2.08(s, 2H), 3H), 3.58(s, 3H), 3.41(s, 3H), 1.99(s, 3H), 1.73(m, 1H), 0.70(d r 6H) 7.33(d r 1H) , 7.23(d, 2H), 6.93(dd, 1H), 6.89(d, 1H) , 1-419 6.83(d 3.40(s , 2H) , 3H) , 5.06(s, , 2.73(d, 2H), 2H), 3.79(s, 3H), 3.56(s, 3H), 2.05(s, 3H), 2.01(s, 3H), 1.74 (m , 1H) , 0.70(d, 6H) 59 Table 5 (continued) No. ^-NMRCCDCla/TMS, 6 value ppm) ] 7.40(d, 1H), 7.16(m, 2H), 5.30(s, 2H), 3.61(t, 2H), 1-421 3.59(s, 2.04(s, 3H) , 3H) , 3.43(s, 1.87(m, 3H) , 1H), 2.80(d, 2H), 1.59(m, 2H), 2.09(s, 1.37(m, 3H), 2H), 0.91(t, 3H) , 0.76(d, 6H) 7.39(d, 1H), 7.18(m, 2H) , 5.31(s, 2H), 3.91(m, 1H), 1-422 3.59(3, 3H) , 3.43(s, 3H) , 2.80(d, 2H), 2.08(s, 3H), 2.04(3, 3H), 1.87(m, 1H), 1.22(d, 6H), 0.77(d, 6H) 7.39(d, 1H), 7.23(m, 2H) , 5.23(s, 2H), 3.58(s, 3H), 1-424 3.43(s, 3H) , 2.80(d/ 2H) , 2.07(s, 6H), 1.89(m, 1H), 1.26(s; 9H) , 0.78(d, 6H) 7.39(d; 1H), 7.17 (m, 2H) , 5.43(d, 1H), 5.22(d, 1H), 1-425 3.68 (m, 2.08(3, 1H), 3H) , 3.59(s, 2.04(s, 3H) , 3H) , 3.43(s, 3H), 1.87(m, 1H), 2.80(d, 1.46-1. 2H), 63(m, 2H), 1.20(d, 3H) , 0.89(t, 3H) , 0.77(dd, 6H) 7.42(d, 1H), 7.10(m, 2H) , 5.43(s, H), 4.14(q, 2H), 1-426 3.58 (s, 3H) , 3.44(s, 3H) , 2.80(d, 2H), 2.05(s, 3H), 2.01(s, 3H) , 1.85(111, 1H), 0.76(d, 6H) 7.40(d 1H) , 7.17(dd / 1H , 7.13(d, 1H) , 5.87-5 .98(m, 1-427 1H), 5 2H) , 3 .32(3, .59(s, 2H), 5. 3H), 3. 29 (dc 44 (s 1, 1H) , 5.20 (dd, 1H) , 3H), 2.80(d, 2H), 2. 4.16(d, 09(s, 3H), 2.04(s 3H) , 1.87(m, 1H) , 0.76(d, 6H) 7.39(d 1H), 7.15(m, 2H) , 5.30(s, 2H) , 3.60(t, 2H), 1-428 3.59(s 2.04(s 3H) , 3H) 3.43(s, 1.88(m, 3H) 1H) , 2.80(d, 2H), , 1.60 (m, 2H), 2.09(s, 1.27(m, 3H), 10H), 0.88(t r 3H) 0.77(d, 6H) 7.49(d , 1H) 7.12(d, 1H) , 7.08(dd, 1H) , 3.68(s , 3H), 1-429 3.46(m , 1H) , 3.46(s, 3H) , 2.88(d, 2H), 2.40(m, 2H), 2.35(s r 3H) 2.25(s, 3H) , 1.84-2.11(m, 5H), 0. 80 (d, 6H) 7.49(d , 1H) , 7.06(d/ 1H) , 6.98(m, 1H), 3.64(s, 3H), 1-448 3.47 (s , 3H) r 2.86(d, 2H) , 2.39(s, 3H), 1.95 (m, 1H), 1.38(s r 9H) , 0.76(d, 6H) 7.49(d , 1H) , 7.18(d, 1H) , 7.13(m, 1H), 4.31(s, 2H), 1-452 3.71(s r 3H) r 3.46(s, 3H) , 3.42(s, 3H), 2.88(d, 2H), 2.32 (s , 3H) , 2.03(m, 1H) , 0.79(d, 6H) 7.53 (d r 1H) r 7.27(d, 1H) , 7.16(dd, 1H) , 3.72(s , 3H), 1-514 3.48(s , 3H) f 2.92(d, 2H) , 2.88(m, 1H) , 2.43(s, 3H), 2.07 (m , 1H) , 1.21(d, 6H) , 0.84(d, 6H) 7.41 (d , 1H) , 7.21(s, 1H) , 7.19(d, 1H), 5.28(s, 2H), 1-515 3.92 (m , 1H) , 3.63(s, 3H) , 3.44(s, 3H), 2.82(d, 2H), 2.19(s r 3H) , 1.94(m, 1H) , 1.21(d, 6H), 0.79(d, 6H) 7.55(d , 1H) , 7.32(d, 1H) , 7.16(dd, 1H) , 3.79(s , 3H), 1-516 3.76(s , 3H) , 3.49(s, 3H) , 2.94(d, 2H), 2.47(s, 3H), 2.14 (m , 1H) , 0.92(d, 6H) 60 Table 5 (continued) No. 1H-NMR[CDC13/TMS, 5 value (ppm) ] 7.53(d, 1H) , 7.28(d/ 1H), 7.18(dd, 1H), 3.74(s, 3H), 1-518 3.47(s, 3H) , 2.92 (m, 1H), 2.91(d/ 2H), 2.42(s, 3H) , 2.07 (m, 1H), 1.23(d, 6H), 0.84(d, 6H) 7.42(d, 1H), 7.22(d, 1H), 7.21(s, 1H), 5.28(s# 2H) , 1-519 3.94(m, 1H), 3.63(s, 3H), 3.44(s, 3H), 2.82(d, 2H) , 2.14(s, 3H), 1.95(m, 1H), 1.21(d, 6H), 0.79(d, 6H) 7.56(d, 1H), 7.35(d, 1H), 7.19(dd, 1H) , 3.81(s, 3H), 1-521 3.76 (s, 3H), 3.50(s, 3H), 2.94(d, 2H), 2.47(s, 3H) , 2.14(m, 1H) , 0.92(d, 6H) 8.17 (br, 1H) , 7.78(d, 1H) , 7.47-7.53(m, 2H), 3.84(s, 1-522 3H) , 3 0.95(d, 47(s, 6H) 3H) , 2 93 (d, 2H), 2.62 (s, 3H), 2.24(m, 1H) , 7.57(d, 1H) , 7.39(d, 1H), 7.22(dd, 1H), 3.84(s, 3H) , 1-523 3.76(s, 3H) , 3.50(s, 3H) , 2.95(d, 2H), 2.46(s, 3H) , 2.15(m, 1H) , 0.92(d, 6H) 7.51(d, 1H), 7.27(d, 1H), 7.20(dd, 1H), 3.74(s, 3H) , 1-524 3.46(s, 3H) , 2.99(m, 1H), 2.90(d, 2H), 2.37(s, 3H) , 2.07(m, 1H), 1.26(d\| 6H), 0.82(d, 6H) 7.55(d, 1H), 7.16(di 1H)# 7.11(dd, 1H), 6.87(s, 1H), 1-539 3.73(s, 3H) , 3.48(s, 3H), 3.31(m, 1H), 2.89(d, 2H), 2.04(m, 1H), 1.27 (d, 6H), 0.79(d, 6H) 7.55(d 1H); 7.20(d, 1H), 7.12(dd, 1H), 7.05 (s, 1H) , 1-540 3.72(s 3H) 3.49(s, 3H), 3.22(m, 1H), 2.90(d, 2H) , 2.05 (m 1H) 1.26(d, 6H), 0.81(d, 6H) 7.56(d 1H) 7.21 (d, 1H), 7.15(s, 1H), 7.12(dd, 1H), 1-541 3.72(s 3H) 3.49(3, 3H), 3.17(m, 1H), 2.91(d, 2H) , 2.05(m 1H) , 1.25(d, 6H), 0.82(d, 6H) 7.57(d 1H) , 7.17(d 1H) 7.09(dd, 1H) , 7.06(s, 1H) , 1-542 3.78(s , 3H) , 3.49(s r 3H) , 3.26(m, 1H), 2.90(d, 2H) , 2.03 (m , 1H) , 1.24(d r 6H) , 0.78(d, 6H) 7.51 (d r 1H) , 7.16(m r 1H) , 6.97(d, 1H), 3.82(s, 3H) , 1-544 3.65 (s r 3H) , 2.63(t r 2H) , 2.27(s, 3H), 2.24(3, 3H) , 2.10(s r 3H) , 2.00(s r 3H) , 1.67(m, 1H), 0.81(d, 6H) 7.47 (d , 1H) , 7.34(d , 1H) , 7.11(m, 1H), 6.94(d, 1H) , 1-545 6.86(d r 1H) , 3.67(s r 3H) , 2.60(t, 2H), 2.51(s, 3H), 2.38 (s , 3H) , 2.28(s r 3H) , 1.73(m, 1H), 0.75(d, 6H) 7.62(s , 1H) , 7.25(s , 1H) , 3.71(s, 3H), 3.50(s, 3H), 2-28 2.88(d , 2H) , 2.38(s , 3H) , 2.32(s, 3H) , 2.24(s, 3H) , 2.02 (m , 1H) , 0.85(d , 6H) 61 Table 5 (continued) No. ^-NMRtCDCls/TMS, 5 value (ppm) ] 2-38 7.41(s, 1H), 7.12(s, 1H), 3.12(s, 3H) , 3.48(s, 3H), 2.88(d, 2H) , 2.38(s, 3H), 2.30(s, 3H), 2.24(s, 3H) , 2.40-2.30(m, 2H) , 2.04(m, 1H), 1.14(t, 3H), 0.85(d, 6H) 2-40 8.26(s, 1H), 7.82(s, 1H) , 7.27(br, 2H) , 3.90(s, 3H) , 3.45(s, 3H) , 2.95(m, 2H), 2.57(s, 3H), 2.32(s, 3H) , 1.71(m, 2H) , 1.02(t, 3H) 2-41 7.37(s, 1H), 7.10(s, 1H), 6.30(s, 1H), 3.59(s, 3H), 3.47(s, 3H) , 3.43(m, 1H) , 2.92(br, 2H) , 2.48(s, 3H) , 2.17(s, 3H) , 1.55(br, 2H) , 1.28(d, 6H) , 0.94(t, 3H) The agrohorticultural agent, in particular, agrohorticultural insecticides or acaricides, containing a substituted pyrazolecarboxanilide derivative represented by the formula (I) or salt of the present invention as an active ingredient, are suitable for controlling various insect pests such as agrohorticultural insect pests, stored grain insect pests, sanitary insect pests, nematodes, etc., which are injurious to paddy rice, fruit trees, vegetables, other crops, flowers and ornamental plants, etc. They have a marked insecticidal effect, for example, on LEPIDOPTERA including summer fruit tortrix (Adoxophes orana fasciata), smaller tea tortrix (Adoxophyes sp.), Manchurian fruit moth (Grapholita inopinata), oriental fruit moth (Grapholita molesta), soybean pod borer (Leguminivora glycinivorella) , mulberry leafroller (Olethreutes mori), tea leafroller (Caloptilia thevivora), Caloptilia sp. (Caloptilia zachrysa), apple leafminer (Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota), common white (Piers rapae crucivora), tobacco budworm (Heliothis sp.), codling moth (Laspey resia pomonella), diamondback moth (Plutella xylostella), apple fruit moth (Argyresthia conjugella), peach fruit moth (Carposina niponensis), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), tobacco moth (Ephestia elutella), mulberry pyralid (Glyphodes pyloalis), yellow rice borer (Scirpophaga incertulas), rice skipper (Parnara guttata), rice armyworm (Pseudaletia separata), pink borer (Sesamia inferens), common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), etc.; 62 HEMIPTERA including aster leafhopper (Macrosteles fascifrons), green rice leafhopper (Nephotettix cincticepts), brown rice planthopper (Nilaparvata lugens), whitebacked rice planthopper (Sogatella furcifera), citrus psylla (Diaphorina citri), grape whitefly (Aleurolibus taonabae), sweetpotato whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodes vaporariorum), turnup aphid (Lipaphis erysimi), green peach aphid (Myzus persicae), Indian wax scale (Ceroplastes ceriferus), cottony citrus scale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex), san Jose scale (Cornstockaspis perniciosa), arrowhead scale (Unaspis yanonensis), etc.; TYLENCHIDA including soybean beetle (Anomala rufocuprea), Japanese beetle (Popillia japonica), tobacco beetle (Lasioderma serricorne), powderpost beetle (Lyctus brunneus), twenty-eight-spotted ladybird (Epilachna vigintiotopunctata), azuki bean weevil (Callosobruchus chinensis), vegetable weevil (Listroderes costirostris), maize weevil (Sitophilus zeamais), boll weevil (Anthonomus grandis grandis), rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora femoralis), rice leaf beetle (Oulema oryzae), striped flea beetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda), Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis), corn rootworm (Diabrotica sp.), etc.; DIPTERA including melon fly (Dacus(Zeugodacus) cucurbitae), oriental fruit fly (Dacus(Bactrocera) dorsalis), rice leafminer (Agnomyza oryzae), onion maggot (Delia antiqua), seedcorn maggot (Delia platura), soybean pod gall midge (Asphondylia sp.), etc.; TYLENCHIDA including root-lesion nematode (Pratylenchus sp.), potato cyst nematode (Globodera rostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode (Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchus avenae), chrysanthemum foliar (Aphelenchoides ritzemabosi), etc.; and ACARINA including citrus red mite (Panonychus citri), fruit tree red spider mite (Panonychus ulmi), carmine spider mite (Tetranychus cinnabarinus), Kanzawa spider mite (Tetranychus Kanzawai Kishida), two-spotted spider mite (Tetranychus urticae Koch), pink tea rust mite (Acaphylla theae), pink citrus rust mite (Aculops pelekassi), purple tea 63 mice (Calacarus carinatus), pear rust mite (Epitrimerus pyri), etc. A substituted pyrazolecarboxanilide derivative represented by the formula (I) or salts thereof of the present invention is used preferably as agrohorticultural insecticides or acaricides. However, the compound exhibits excellent control effect against various insect pests such as insect pests for forest and wood, insect pests for livestock farming, sanitary insect pests, etc. and can be used as pest control agents in various wide fields. Examples of insect pests include: Tabanidae such as Tabanus rufidens Bigot; Muscidae such as housefly (Musca domestica uicina MACQUART); Gasterophilidae such as horse bot fly (Gasterophilus intestinalis); Hypodermatidae such as cattle grub (Hypoderma bov fS bouis L.); Phoridae such as Megaselia spiracularis; Culicidae such as pale house mosquito (Culex pipiens pallens), Anopheles sinensis, one-striped mosquito (Aedes albopictus), and Aedes japonicus; Pulicidae such as cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), human flea (Pulex irritans); Ixodidae such as Ixodes ovatus Neumann; Lymantriidae such as Euproctis similes; Rhynchophoridae such as rice weevil (Sitophilus zeamais); Vespidae such as Vespa simillima xanthoptera Cameron; Blattellidae such as German cockroach (Blattela germanica); Blattidae such as American cockroach (Periplaneta americana) and Periplaneta japonica; Pthiridae such as public-louse (Phthirus pubis); Termitidae such as Japanese termite (Reticulitermes speratus) and house termite (Coptotermes formosanus); and Ixodidae such as Ixodes persulcatus; and Macronyssidae such as tropical rat mite (Ornithonyssus bacoti). The agrohorticultural agent, in particular, agrohorticultural insecticides or acaricides, containing a substituted pyrazolecarboxanilide derivative represented by the formula (I) or salt thereof of the present invention as an active ingredient has a marked controlling effect on the above-exemplified insect pests, which are injurious to paddy field crops, upland crops, fruit trees, vegetables and other crops, flowers and ornament plants, and the like. Therefore, the desired effect of the agrohorticultural insecticides of 64 the present invention can be exhibited by applying the agents to paddy field, field, fruit trees, vegetables, other crops, seeds of flowers and ornament plants, paddy field water, stalks and leaves, or soil at a season at which the insect pests are expected to appear, before their appearance or at the time when their appearance is confirmed. Plants, for which an agrohorticultural agent of the present invention can be used, are not specifically limited and include, for example, plants shown hereinbelow: Cereals (e.g. rice (Oryza sativa), barley (Hordeum vulgare), wheat (Triticum aestivum L.), rye (Secale cereale), oat (Avena), maize (Zea mays L.), kaoliang, etc.); legume (soybean, adzuki bean, fava bean, bean, peanut, etc.); fruit trees and fruits (apple, citrus fruits, pear, grapes, peach, plum, cherry, walnut, almond, banana, strawberry, etc.); vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, welsh onion, green pepper, etc.); root vegetables (carrot, potato, sweet potato, radish, lotus root, turnip, etc.); crop for processing (cotton, flax (Linum usitatissimum), paper mulberry (Broussonetia kasinoki SIEB), paperbush (Edgeworthia papyrifera), rape (Brassica napus L.), beet (Beta vulgaris), hop, sugar cane (Saccbar-a-tum of f icinarum) , sugar beet (Beta vulgaris var. saccharifera), olive, rubber, coffee, tobacco, tea, etc.); gourd (pumpkin, cucumber, watermelon, melon, etc.); grass (orchard grass, sorghum, timothy, clover, alfalfa, etc.); grass (Korean lawn grass, bent grass, etc.); crop for spicery (lavender (Lavandula officinalis CHAIX), rosemary, thyme, parsley, pepper, ginger, etc.); and flowers (chrysanthemum, rose, orchid, etc.). Recently, gene recombinant crop (herbicide resistant crop, insect pest resistant crop incorporated with insecticidal toxin generating gene, disease resistant crop incorporated with disease resistance inducer producing gene, taste improved crop, preservability improved crop, yield improved crop, etc.), insect sex pheromone (pheromone disrupting chemicals for leaf roller moths, cabbage armyworm, etc.), IPM (integrated pest management) technology using natural enemy insect have been progressed, and pesticide compositions of the present invention can be used in combination with or by 65 systematization with such technologies. The agrohorticultural agent of the present invention is generally prepared into conveniently usable forms according to an ordinary manner for formulation of agrochemicals. That is, the substituted pyrazolecarboxanilide derivative represented by the formula (I) or salt of the present invention and, optionally, an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable formulation form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, water dispersible granule, granules, dust, tablets, pack or the like through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking. The inert carrier usable in the present invention may be either solid or liquid. As a material usable as the solid carrier, there can be exemplified soybean flour, cereal flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residue of vegetables, resins such as powdered synthetic polymers and the like, clays (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talc and pyrophyllite), silica powders or flakes (e.g. diatomaceous earth, silica sand, mica and white carbon [synthetic, high-dispersion silicic acid, also called finely divided hydrated silica or hydrated silicic acid, some of commercially available products contain calcium silicate as the major component]), inorganic or mineral powders such as activated carbon, powdered sulfur, pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate, calcium phosphate and the like, plastic carriers such as polyethylene, polypropylene, poly(vinylidene chloride) and the like, chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium chloride), and compost. These carriers may be used alone or as a mixture of two or more kinds thereof. A material usable as the liquid carrier is selected from materials that have solubility in themselves or which, even without such solubility, are capable of dispersing an active ingredient with the aid of an adjuvant. The following are typical examples of the liquid carrier and can be used alone 66 or as a mixture of two or more kinds thereof: water, alcohols (e.g. methanol, ethanol, isopropanol, butanol and ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone), ethers (e.g. ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydrofuran), aliphatic hydrocarbons (e.g. kerosene and mineral oils), aromatic hydrocarbons (e.g. benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes), halogenated hydrocarbons (e.g. dichloroethane, chloroform, carbon tetrachloride and chlorobenzene), esters (e.g. ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate), amides (e.g. dimethylformamide, diethylformamide and dimethylacetamide), nitriles (e.g. acetonitrile), and dimethyl sulfoxide. The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination of two or more kinds, or in some cases, need not be used at all. To emulsify, disperse, dissolve and/or wet a compound as active ingredient, a surfactant is used. As the surfactant, there can be exemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resonates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalene sulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters. Further, to stabilize the dispersion of a compound as active ingredient, tackify it and/or bind it, the adjuvants exemplified below may also be used, namely, there may also be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum arabic, poly(vinyl alcohol)s, turpentine, bran oil, bentonite and ligninsulfonates. To improve the flowability of a solid product, the following adjuvants may also be used, namely, there may be used adjuvants such as waxes, stearates, alkyl phosphates, etc. Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptizer for dispersible products 67 Adjuvants such as silicone oils may also be used as a defoaming agent. Adjuvants such as 1,2-benzisothiazoline-3-one, p-chloro- m-xylenol, butyl p-hydroxybenzoate may also be added as a preservative. Further, if necessary, functional spreading agents, active enhancers such as metabolic decomposition inhibitor like piperonyl butoxide, anti-freezing agents such as propylene glycol, antioxidants such as BHT, ultraviolet absorbers, and the other additives may also be added. The content of the compound as active ingredient may be varied as required, and the compound as active ingredient may be used in a proportion properly chosen in the range of 0.01 to 90 parts by weight per 100 parts of the agrohorticultural agents. For example, in dusts or granules, the suitable content of the compound as active ingredient is from 0.01 to 50 % by weight. In emulsifiable concentrate or wettable powders, it is also from 0.01 to 50 % by weight. The agrohorticultural agent of the present invention is used to control a variety of insect pests in the following manner: it is applied to a crop on which the insect pests are expected to appear, or a site where appearance or growth of the insect pests is undesirable, as it is or after being properly diluted with or suspended in water or the like, in an amount effective for control of the insect pests. The applying dosage of the agrohorticultural agent of the present invention is varied depending upon various factors such as a purpose, insect pests to be controlled, a growth state of a plant, tendency of insect pests appearance, weather, environmental conditions, a formulation form, an application method, an application site and application time. It may be properly chosen in the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, (in terms of the compound as active ingredient) per 10 ares depending upon purposes. The agrohorticultural agent of the present invention may be used in admixture with other agrohorticultural insecticides, acaricides, nematocides, fungicides, biotic pesticides or the like in order to expand both spectrum of controllable insect pest species and the period of time when effective application 68 are possible or to reduce the dosage. Furthermore, the agrohorticultural insecticide of the present invention may be used in admixture with herbicides, plant growth regulators, fertilizers or the like, depending upon application situations. As the other agrohorticultural insecticides, acaricides and nematocides, which are used for the above purpose, there can be exemplified agrohorticultural insecticides, acaricides and nematocides, such as Ethion, Trichlorfon, Metamidophos, Acephate, Dichlorvos, Mevinphos, Monocrotophos, Malathion, Dimethoate, Formothion, Mecarbam, Vamidothion, Thiometon, Disulfoton, Oxydeprofos, Naled, Methylparathion, Fenitrothion, Cyanophos, Propaphos, Fenthion, Prothiofos, Profenofos, Isofenphos, Temephos, Phenthoate, Dimethylvinphos, Chlorfenvinphos, Tetrachlorvinphos, Phoxim, Isoxathion, Pyraclofos, Methidathion, Chlorpyrifos, Chlorpyrifos-methyl, Pyridaphenthion, Diazinon, Pirimiphosmethyl, Phosalone, Phosmet, Dioxabenzophos, Quinalphos, Terbuphos, Ethoprophos, Cadusafos, Mesulfenfos, Spirodiclofen, Metaflumizone, Flubendiamide, DPS (NK-0795), Phosphocarb, Fenamiphos, Isoamidophos, Fosthiazate, Isazophos, Ethoprophos, Fenthion, Fostietane, Dichlofenthion, Thionazin, Sulprofos, Fensulfothion, Diamidafos, Pyrethrin, Allethrin, Prallethrin, Resmethrin, Permethrin, Tefluthrin, Bifenthrin, Fenpropathrin, Cypermethrin, a-Cypermethrin, Cyhalothrin, X-Cyhalothrin, Deltamethrin, Acrinathrin, Fenvalerate, Esfenvalerate, Cycloprothrin, Ethofenprox, Halfenprox, Silafluofen, Flucythrinate, Fluvalinate, Methomyl, Oxamyl, Thiodicarb, Aldicarb, Alanycarb, Cartap, Metolcarb, Xylylcarb, Propoxur, Phenoxycarb, Fenobucarb, Ethiophencarb, Fenothiocarb, Bifenazate, BPMC, Carbaryl, Pirimicarb, Carbofuran, Carbosulfan, Furathiocarb, Benfuracarb, Aldoxycarb, Diafenthiuron, Diflubenzuron, Teflubenzuron, Hexaflumuron, Novaluron, Lufenuron, Flufenoxuron, Chlorfluazuron, Fenbutatin oxide, Tricyclohexyltin hydroxide, Sodium oleate, Potassium oleate, Methoprene, Hydroprene, Binapacryl, Amitraz, Dicofol, Kersen, Chlorobenzilate, Bromopropylate, Tetradifon, Bensultap, Benzoximate, Tebufenozide, Methoxyfenozide, Pyridalyl, Chromafenozide, Propargite, Acequinosyl, Endosulfan, Diofenolan, Chlorfenapyl, Fenpyroximate, Tolfenpyrad, Fipronil, 69 Tebufenpyrad, Triazamate, Etoxazole, Hexythiazox, Nicotine sulfate, Nitenpyram, Acetamiprid, Thiacloprid, Imidacloprid, Thiamethoxam, Clothianidin, Dinotefuran, Fluazinam, Pyriproxyfen, Hydramethylnon, Pyrimidifen, Pyridaben, Cyromazine, TPIC (tripropyl isocyanurate), Pymetrozin, Clofentezin, Buprofedin, Thiocyclam, Fenazaquin, Chinomethionate, Indoxacarb, Polynactin complexes, Milbemectin, Abamectin, Emamectin-benzoate, Spinosad, BT (Bacillus thuringiensis), Azadirachtin, Rotenone, Hydroxypropyl starch, Levamisole hydrochloride, Metam-sodium, Morantel tartrate, Dazomet, Trichlamide, Pasteuria penetrans, Monacrosporium- phymatophaguiti, etc. As the agrohorticultural fungicides used for the same purpose as above, there can be exemplified agrohorticultural fungicides such as Sulfur, Lime sulfur, Copper sulfate basic, Iprobenfos, Edifenfos, Tolclofos-methyl, Thiram, Polycarbamate, Zineb, Maneb, Mancozeb, Propineb, Thiophanate, Thiophanate methyl, Benomyl, Iminoctadin acetate, Iminocutadin albecylate, Mepronil, Flutolanil, Pencycuron, Furametpyl, Thifluzamide, Metalaxyl, Oxadixyl, Carpropamid, Dichlofluanid, Flusulfamide, Chlorothalonil, Kresoxim-methyl, Fenoxanil, Himexazol, Etridiazol, Fluoroimide, Procymidone, Vinclozolin, Iprodione, Triadimefon, Bitertanol, Triflumizole, Ipconazole, Fluconazole, Propiconazole, Diphenoconazole, Myclobutanil, Tetraconazole, Hexaconazole, Tebuconazole, Thiadinil, Imibenconazole, Prochloraz, Pefurazoate, Cyproconazole, Isoprothiolane, Fenarimol, Pyrimetanil, Mepanipyrim, Pyrifenox, Fluazinam, Triforine, Diclomezine, Azoxystrobin, Thiadiazin, Captan, Probenazole, Acibenzolar-S-methyl, Fthalide, Tricyclazole, Pyroquilon, Chinomethionat, Oxolinic acid, Dithianon, Kasugamycin, Validamycin, Polyoxin, Blasticidin, Streptomycin, etc. Similarly, as the herbicides, there can be exemplified herbicides such as Glyphosate, Sulfosate, Glyfosinate, Bialaphos, Butamifos, Esprocarb, Prosulcarb, Benthiocarb, Pyributycarb, Asulam, Linuron, Dymron, Isouron, Bensulfuron methyl, Cyclosulfamuron, Cinosulfuron, Pyrazosulfuron ethyl, Azimsulfuron, Imazosulfuron, Tenylchlor, Alachlor, Pretilachlor, Clomeprop, Etobenzanid, Mefenacet, Pendimethalin, 70 Bifenox, Acifluorfen, Lactfen, Cyhalofop-butyl, Ioxynil, Bromobutide, Alloxydim, Setoxydim, Napropamide, Indanofan, Pyrazolate, Benzofenap, Pyraflufen-ethyl, Imazapyl, Sulfentrazone, Cafenstrole, Bentoxazon, Oxadiazon, Paraquat, Diquat, Pyriminobac, Simazine, Atrazine, Dimethametryn, Triazyflam, Benflesate, Flutiacet-methyl, Quizalofop-ethyl, Bentazon, Calcium peroxide, etc. As to the biotic pesticides, the same effect as above can be expected by using the agrohorticultural agent of the present invention in admixture with, for example, viral formulations obtained from nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), entomopox virus (EPV), etc.; microbial pesticides utilized as insecticides or nematicides, such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, etc.; microbial pesticides utilized as fungicides, such as Trichoderma lignorum, Agrobacterium radiobactor, nonpathogenic Erwinia carotovora, Bacillus subtilis, etc.; and biotic pesticides utilized as herbicides, such as Xanthomonas campestris, etc. In addition, the agrohorticultural agent of the present invention can be used in combination with biotic pesticides including natural enemies such as Parasitic wasp (Encarsia formosa), Parasitic wasp (Aphidius colemani), Gall-mildge (Aphidoletes aphidimyza), Parasitic wasp (Diglyphus isaea), Parasitic mite (Dacnusa sibirica), Predatory mite (Phytoseiulus persimilis), Predatory mite (Amblyseius cucumeris), Predatory bug (Orius sauteri), etc.; microbial pesticides such as Beauveria brongniartii, etc.; and pheromones such as (Z)-10-tetradecenyl acetate, (E,Z)-4,10- tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-ll- tetradecenyl acetate, (Z)-13-icosen-10-one, -f&}—8-dodoconyl acetate,—(Z)-ll-tetradecenyl acetate,—(Z)-13-icosen-lfl-one, 14-methyl-l-octadecene, etc. Examples The substituted pyrazolecarboxanilide derivatives represented by the formula (I), and substituted aniline derivative represented by the formula (II) and substituted pyrazolecarboxic acid represented by the formula (IV), which 71 are intermediates therefore, of the present invention, are explained in the following by referring to Examples, which are not to be construed as limitative. Example 1 Production of 1,3-dimethyl-5- trifluoromethylpyrazole-4-carboxylic acid (compound No. 4-1) 4-Iodo-l,3-dimethyl-5-trifluoromethylpyrazole (8.7 g, 30 mmol) was dissolved in tetrahydrofuran (87 ml), and a solution (1.6 M, 28 ml) of n-butyl lithium in hexane was slowly added under an argon atmosphere with cooling with dryice-acetone (not higher than -60°C) . After stirring at -70°C for 30 min, the mixture was gradually warmed to room temperature while blowing in carbon dioxide. The reaction mixture was poured into water, the organic layer was removed, and the aqueous layer was acidified with hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained crude crystals were washed with hexane to give the desired compound (4.67 g) as crystals, yield 74% Property: melting point 124 - 125.5°C Example 2 Production of N-{3-isobutyl-4-[l-methoxy-2,2,2- trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3- trifluorornethylpyrazole-4-carboxamide (compound No. 1-211) 1,5-Dimethyl-3-trifluoromethylpyrazole-4-carboxylic acid (2.09 g, 10 mmol) was dissolved in thionyl chloride, and the mixture was heated under reflux for 3 hr. The mixture was concentrated under reduced pressure to give 1,5-dimethyl-3- trifluoromethylpyrazole-4-carbonyl chloride. This was added to a solution of 3-isobutyl-4-[l-methoxy-2,2,2-trifluoro-1- (trifluoromethyl)ethyl]aniline (3.29 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in tetrahydrofuran (30 ml), and the mixture was heated under reflux for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over magnesium sulfate. After concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=l:l) to give the desired compound (3.64 g) as crystals, yield 70% 72 Property: melting point 138-139°C Example 3 Production of N-methoxymethyl-N-{3-isobutyl-4-ti- me thoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5- dimethyl-3-trifluoromethylpyrazole-4-carboxamide (compound No. 1-222) Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-ti- me thoxy-2, 2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-l,5- dimethyl-3-trifluoromethylpyrazole-4-carboxamide (250 mg, 0.48 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of chloromethyl methyl ether (64 mg, 0.8 mmol) in tetrahydrofuran (2 ml) was added and the mixture was stirred for 5 hr. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:l) to give the desired compound (238 mg). yield: 88% Property: nD1.4669 (22.4°C) Example 4 Production of 2-methyl-5-n-propyl-4-[1,2,2,2- tetrafluoro-1-(trifluoromethyl)ethyl]aniline (compound No. 3- 1) 5-n-Propyl-2-methylaniline (14.9 g, 0.1 mol) was diluted in a mixed solvent (300 ml) of tert-butyl methyl ether-water (1:1), and heptafluoroisopropyl iodide (29.6 g, 0.1 mol), tetrabutylammonium hydrogen sulfate (3.4 g, 0.01 mol), sodium hydrogen carbonate (8.4 g, 0.1 mol) and sodium dithionite (17 g, 0.1 mol) were successively added. The mixture was stirred overnight at room temperature. The reaction mixture was diluted in hexane, washed twice with 3N hydrochloric acid, and washed with aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate 5:1) to give the desired compound (28.5 g). yield:90% Property: ^-NMRfCDCWTMS, 5 value (ppm) ] 7.09(s, 1H) , 6.54(s, 73 1H) , 3.76(bs, 2H) , 2.63(111, 2H) , 2.13(s, 3H) , 1.58(m, 2H) , 0.96(t, 3H) Example 5 Production of 4-[l-methoxy-2,2,2-trifluoro-l- (trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline (compound No. 3-3) 2-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-l- (trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) was dissolved in a 28% solution (9.6 g) of sodium methoxide in methanol, and the mixture was heated under reflux for 3 hr. After allowing to cool, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:l) to give the desired compound (1.31 g). yield: 79% Property: ^-NMRtCDCla/TMS, 5 value (ppm) ] 7.10 (s, 1H) , 6.66 (s, 1H), 3.72(bs, 2H) , 3.42(s, 3H) , 2.84(m, 2H) , 2.14(s, 3H) , 1.61(m, 2H), 1.00(t, 3H) Example 6 Production of 2-methyl-5-n-propyl-4-[2,2,2- trifluoro-1-(trifluoromethyl)ethyl]aniline (compound No. 3-2) 2-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) was dissolved in dimethyl sulfoxide (20 ml), sodium borohydride (378 mg, 10 mmol) was added by small portions, and the mixture was stirred at 60°C for 5 hr. Ice was added to the reaction mixture by small portions, and then acetic acid was added dropwise. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed 4 times with water, dried over magnesium sulfate and concentrated under reduced pressure to give the desired compound (1.47 g) . yield:99% Property: ^-NMRfCDCla/TMS, 5 value (ppm)] 7.18(s, 1H) , 6.54(s, 1H), 4.45-4.20(br, 2H), 4.27(m, 1H), 2.50(dd, 2H), 2.14(s, 3H), 1.57(m, 2H), 0.98(t, 3H) Example 7 Production of N-{4-[l-methoxy-2,2,2-trifluoro-l- (trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5- trimethylpyrazole-4-carboxamide (compound No. 2-15) 1,3,5-Trimethylpyrazole-4-carbonyl chloride (172 mg, 1 74 mmol), 4-[l-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]- 2-methyl-5-n-propylaniline (329 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) were dissolved in tetrahydrofuran (10 ml), and the mixture was heated under reflux for 3 hr. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=l:2) to give the desired compound (3 60 mg). yield: 77% Property: melting point 132-134°C Example 8 Production of N-acetyl-N-{4-[l-methoxy-2,2,2- trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n- propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 2-16) Sodium hydride (32 mg, 60%,0.8 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{4-[1-methoxy- 2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n- propylphenyl}-l,3,5-trimethylpyrazole-4-carboxamide (250 mg, 0.53 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of acetic anhydride (80 mg, 0.78 mmol) in tetrahydrofuran (2 ml) was added, and the mixture was stirred for one day. The reaction mixture was poured into diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=l:3) to give the desired compound (139 mg). yield: 52% Property: nD1.4905 (25.9°C) Example 9 Production of N-{2-methyl-5-n-propyl-4-[2,2,2- trifluoro-l- (trifluoromethyl)ethyl]phenyl-2-methyl-5-n- propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound No. 2-13) In the same manner as in Example 7 except that 2-methyl- 5-n-propyl-4-[2,2,2-trifluoro-l-(trifluoromethyl)ethyl]aniline was used instead of 4-[l-methoxy-2,2,2-trifluoro-1- (trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline, the 75 reaction is carried out for 3 hr to give the desired compound, yield: 66% Property: melting point 128-131°C Example 10 Production of N-{3-isobutyl-4-[l-methoxy-2,2,2- trifluoro-1-(trifluoromethyl)ethyl]phenyl}-l,3,5- trimethylpyrazole-4-carboxamide (compound No. 1-155) 1,3,5-trimethylpyrazole-4-carbonyl chloride (3.93 g, 22.8 mmol), 3-isobutyl-4-[l-methoxy-2, 2, 2-trifluoro-1- (trifluoromethyl)ethyl]aniline (5.0 g, 15.2 mmol), and triethylamine (3.07 g, 30.4 mmol) were dissolved in tetrahydrofuran (100 ml), and the mixture was heated under reflux for 5 hr. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crude crystals were washed with ether to give the desired compound (5.62 g). yield: 80% Property: melting point 189-190°C Example 11 Production of N-ethoxymethyl-N-{3-isobutyl-4-ti- me thoxy-2 ,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}- l,3,5-trimethylpyrazole-4-carboxamide (compound No. 1-145) Sodium hydride (29 mg, 60%,0.73 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-ti- me thoxy-2, 2,2-trifluoro-l- (trifluoromethyl)ethyl]phenyl}- 1,3,5-trimethylpyrazole-4-carboxamide (260 mg, 0.48 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of chloromethyl ethyl ether (70 mg, 0.73 mmol) in tetrahydrofuran (2 ml) was added, and the mixture was stirred for one day. The reaction mixture was poured into diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=l:3) to give the desired compound (200 mg). yield: 69% Property: nD1.4892 (22.4°C) Example 12 Production of N-isobutyloxycarbonyl-N-{3-isobutyl- 4-[l-methoxy-2,2,2-trifluoro-l-(trifluoromethyl)ethyl]phenyl}- 76 l,3,5-trimethylpyrazole-4-carboxainide (compound No. 1-152) Sodium hydride(29 mg, 60%,0.73 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-ti- me thoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}- 1,3,5-trimethylpyrazole-4-carboxamide (260 mg, 0.48 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of isobutyl chlorocarbonate (100 mg, 0.73 mmol) in tetrahydrofuran (2 ml) was added, and the mixture was stirred for one day. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=l:l) to give the desired compound (280 mg). yield: 91% Property: nD1.4829 (22.3°C) Example 13 Production of N-{3-isobutyl-4-[2,2,2-trifluoro-l- (trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4- carboxamide (compound No. 1-123) 1,3,5-Trimethylpyrazole-4-carbonyl chloride (2.09 g, 10.0 mmol), 3-isobutyl-4-[2,2,2-trifluoro-1- (trifluoromethyl)ethyl]aniline (2.0 g, 6.69 mmol), and triethylamine (1.35 g, 13.4 mmol) were dissolved in tetrahydrofuran (60 ml), and the mixture was heated under reflux for 5 hr. The reaction mixture was diluted with ethyl acetate, and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=l:3) to give the desired compound (2.41 g). yield: 77% Property: melting point 148-151°C Example 14 Production of N-acetyl-N-{3-isobutyl-4-[2,2,2- trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5- trimethylpyrazole-4-carboxamide (compound No. 1-125) Sodium hydride (38 mg, 60%, 0.96 mmol) was suspended in tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4- [2,2,2-trifluoro-l- (trifluoromethyl)ethyl]phenyl}-l,3,5- 77 trimethylpyrazole-4-carboxamide (300 mg, 0.64 mmol) in tetrahydrofuran (5 ml) was added dropwise. After stirring at room temperature for 30 min, a solution of acetyl chloride (75 mg, 0.96 mmol) in tetrahydrofuran (2 ml) was added, and the mixture was stirred for one day. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=l:3) to give the desired compound (90 mg). yield: 28% Property: nD1.5021 (22.5°C) Reference Example Production of 1 4-iodo-l,3-dimethyl-5- trifluoromethylpyrazole Iodine (30 g) was dissolved in 60% sulfuric acid (fuming, 80 g) , and 1,3-dimethyl-5-trifluoromethylpyrazole (13.12 g, 80 mmol) was slowly added under ice-cooling. The mixture was stirred at 0°C for 2 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained crude crystals were washed with hexane to give the desired compound (20 g) as crystals, yield 86% Property: ^-NMRtCDCls/TMS, 5 value (ppm) ] 3.98(s, 3H) , 2.26(s, 3H) Typical formulation examples and test example of the present invention are described below but they should not be construed as limiting the scope of the invention. As used in the examples, the terms "part" and "parts" are by weight. Formulation Example 1 Each compound listed in Table 1 or Table 2 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl 10 parts ether and calcium alkylbenzenesulfonate An emulsifiable concentrate was prepared by mixing 78 uniformly the above ingredients to effect dissolution. Formulation Example 2 Each compound listed in Table 1 or Table 2 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts A dust was prepared by mixing uniformly and grinding the above ingredients. Formulation Example 3 Each compound listed in Table 1 or Table 2 5 parts Mixed powder of bentonite and clay 90 parts Calcium ligninsulfonate 5 parts Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying. Formulation Example 4 Each compound listed in Table 1 or Table 2 20 parts Mixture of kaolin and synthetic high-dispersion silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts A wettable powder was prepared by mixing uniformly and grinding the above ingredients. Test Example 1: Acaricidal action on two-spotted spider mite (Tetranychus urticae) Kidney bean leaf disk with a diameter of 2 cm was placed on the wetted filter paper. Ten adult females of two-spotted spider mite were inoculated on each leaf disk, and were sprayed with 50 ml of test solution, prepared by diluting a formulation containing each compound listed in Table 1 or Table 2 as an active ingredient to adjust each of the concentrations to 500 ppm, 50 ppm and 5 ppm. . Two days after the treatment, the survived mites were counted. The corrected mortality was calculated by the following equation and the acaricidal activity was judged according to the criterion shown below. The experiment was carried out with two replicates under the condition at 25°C. 79 Corrected mortality = (%) Number of survived mites in — untreated group Number of survived mites in treated group x 100 Number of survived mites in untreated group Criterion: A Corrected mortality 100% B Corrected mortality 99%-90% C Corrected mortality 89%-80% D Corrected mortality 79%-50% As comparative compounds, compound Nos. 1-163 and 1-164 disclosed in JP-A-2003-48878 were used. ( 1-163 ) ( 1-164 ) As a result of the above-mentioned test, the compound Nos. 1-1, 1-3, 1-4, 1-6, 1-8, 1-10, 1-12, 1-13, 1-15, 1-16, 1-25 to 1-28, 1-31, 1-34 to 1-37, 1-45, 1-47 to 1-49, 1-51 to 54, 1-56, 1-57, 1-59, 1-67, 1-69 to 1-72, 1-74 to 1-76, 1-89, 1-101 to 1-114, 1-120 to 1-160, 1-176 to 1-225, 1-228, 1-234, 1-246, 1- 258, 1-260, 1-266, 1-270, 1-282, 1-285, 1-294, 1-306 to 1-325, 1-327 to 1-332, 1-335 to 1-337, 1-339 to 1-342, 1-344 to 1-358, 1-361 to 1-373, 1-375 to 1-380, 1-382 to 1-384, 1-386 to 1-389, 1-391 to 1-394, 1-396, 1-399 to 1-406, 1-412 to 416, 1-420 to 1-423, 1-425 to 1-427, 1-429 to 1-433, 1-435 to 1-439, 1-441 to 1-445, 1-448, 1-450 to 1-452, 1-454 to 1-463, 1-467 to 1- 470, 1-473, 1-477, 1-478, 1-482 to 1-487, 1-489 to 1-493, 1- 496 to 1-502, 1-510, 1-514, 1-515, 1-518, 1-519, 1-523 to 1- 527, 1-531, 1-539 to 1-541, 1-546 to 1-549, 2-13, 2-15 to 2-17, 2-21 to 2-23, 2-25, 2-34, 2-36 to 39, 2-41 to 43 and 2-45 of 80 the present invention showed A activity at any concentration of 500 ppm, 50 ppm and 5 ppm, and the compound Nos. 1-23, 1-32, 1-78, 1-173, 1-284, 1-326, 1-334, 1-338, 1-343, 1-385, 1-397 to 1-398, 1-408, 1-410, 1-417, 1-440, 1-447, 1-449, 1-464, 1- 472, 1-475, 1-476, 1-479, 1-480, 1-504 to 1-506, 1-509, 1-521, 1-529, 1-530, 1-533, 1-542, 2-26 to 2-33, 2-40 and 2-46 showed A activity at any concentration of 500 ppm and 50 ppm. In contrast, the both control compounds did not show an acaricide activity even at the concentration of 500 ppm. Industrial Applicability According to the present invention, agrohorticultural agents, particularly insecticides and acaricides, having superior properties as compared to conventional techniques can be provided. This application is based on patent application Nos. 234405/2005, 322531/2005 and 114937/2006 filed in Japan, the contents of which are hereby incorporated by reference. While this invention has been shown and described with references to preferred embodiments thereof, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the scope of the invention encompassed by the appended claims. All patents, patent publications and other publications identified or referenced herein are incorporated by reference in their entirety. 81 Claims 1. A substituted pyrazolecarboxanilide derivative represented by the formula (I): Y2m T\|LT (i) CF3 wherein R1 is la) a hydrogen atom, 2a) a Ci-C8 alkyl group, 3a) a halo Ci-C6 alkyl group, 4a) a C1-C6 alkylcarbonyl group, 5a) a halo Ci-C6 alkylcarbonyl group, 6a) a C2-C6 alkenylcarbonyl group, 7a) a halo C2-C6 alkenylcarbonyl group, 8a) a Ci-C6 alkylcarbonyl Ci-C6 alkyl group, 9a) a C3-C6 cycloalkyl group, 10a) a halo C3-C6 cycloalkyl group, 11a) a C3-C6 cycloalkyl Ci-C6 alkyl group, 12a) a halo C3-C6 cycloalkyl Ci-C6 alkyl group, 13a) a C2-C6 alkenyl group, 14a) a halo C2-C6 alkenyl group, 15a) a C2-C6 alkynyl group, 16a) a halo C2-C6 alkynyl group, 17a) a C1-C10 alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy Ci-C6 alkyl group, 20a) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group, 21a) a Ci-C6 alkylthio Ci-C6 alkyl group, 22a) a halo Ci-C6 alkylthio Ci-C6 alkyl group, 23a) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 24a) a halo Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 25a) a C1-C6 alkylsulfonyl Ci-C6 alkyl group, 2 6a) a halo Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 27a) a mono Ci-C6 alkylamino Ci-C6 alkyl group, 28a) a di C1-C6 alkylamino C1-C6 alkyl group wherein the alkyl groups are the same or different, 29a) a phenyl Ci-C6 alkoxy C1-C6 alkyl group, 30a) a substituted phenyl C1-C6 alkoxy Ci-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo 82 Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6 alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group, 34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6 alkylthiocarbonyl group, 3 6a) a mono Ci-C6 alkylaminocarbonyl group, 37a) a di Ci-Ce alkylaminocarbonyl group wherein the alkyl groups are the same or different, 38a) a C1-C6 alkoxycarbonyl Ci-C6 alkyl group, 39a) a Ci-C6 alkylsulfonyl group, 40a) a halo C1-C6 alkylsulfonyl group, 41a) a cyano C1-C6 alkyl group, 42a) a phenyl Ci-C6 alkyl group, 43a) a substituted phenyl Ci-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a substituted phenylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-Cs alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a) a substituted heterocyclylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci- Ca alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, 83 i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulf inyl group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 50a) a phenoxy Ci-C6 alkylcarbonyl group, 51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-Ce alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulf inyl group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 54a) a di Ci-C6 alkylphosphono group 84 wherein the alkyl groups are the same or different, 55a) a di Ci-C6 alkylphosphonothio group wherein the alkyl groups are the same or different, 56a) a W-Ci-C6 alkyl-2\J-Ci-C6 alkoxycarbonylaminothio group, 57a) a N-Ci-C6 alkyl-A/-Ci-C6 alkoxycarbonyl Ci-C6 alkylaminothio group, 58a) a di Ci-C6 alkylaminothio group wherein the alkyl groups are the same or different, 59a) a C3-C6 cycloalkylcarbonyl group, 60a) a halo C3-C6 cycloalkylcarbonyl group, 61a) a Ci-C6 alkyl C3-C6 cycloalkylcarbonyl group, 62a) a halo Ci-C6 alkyl C3-C6 cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-Cs alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-Cs alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 67a) a C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl group, 69a) a halo C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group, 70a) a phenoxy Ci-C6 alkoxycarbonyl group, 71a) a substituted phenoxy C1-C6 alkoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 85 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulf onyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 72a) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl group, 73a) a Ci-C6 alkylcarbonyl Ci-C6 alkylcarbonyl group, or 74a) a Ci-Cs alkoxycarbonyl Ci-C6 alkylcarbonyl group; R2 is lb) a hydrogen atom, 2b) a halogen atom, 3b) a Ci-C6 alkyl group, 4b) a halo Ci-C6 alkyl group, 5b) a cyano group, 6b) a hydroxy group, 7b) a Ci-C6 alkoxy group, 8b) a halo Ci-C6 alkoxy group, 9b) a Ci-C6 alkoxy C1-C3 alkoxy group, 10b) a halo Ci-C6 alkoxy C1-C3 alkoxy group, lib) a Ci-C6 alkylthio C1-C3 alkoxy group, 12b) a halo Ci-C6 alkylthio C1-C3 alkoxy group, 13b) a Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 14b) a halo Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 15b) a Ci-C6 alkylsulfonyl Ci~ C3 alkoxy group, 16b) a halo Ci-C6 alkylsulfonyl C1-C3 alkoxy group, 17b) a mono Ci-C6 alkylamino C1-C3 alkoxy group, 18b) a di C1-C6 alkylamino C1-C3 alkoxy group wherein the alkyl groups are the same or different, 19b) a Ci-C6 alkylthio group, 20b) a halo Ci-C6 alkylthio group, 21b) a Ci-C6 alkylsulfinyl group, 22b) a halo Ci-C6 alkylsulfinyl group, 23b) a Ci-C6 alkylsulfonyl group, 24b) a halo Ci-C6 alkylsulfonyl group, 25b) an amino group, 2 6b) a mono Ci-C6 alkylamino group, 27b) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, 28b) a phenoxy group, 29b) a substituted phenoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 30b) a phenylthio group, 31b) a substituted phenylthio group having, 86 on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 32b) a phenylsulfinyl group, 33b) a substituted phenylsulfinyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 34b) a phenylsulfonyl group, 35b) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 36b) a phenyl C1-C6 alkoxy group, or 37b) a substituted phenyl C1-C6 alkoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci- C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl 87 group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group; G is 1c) a C2-Cio alkyl group, 2c) a halo C2-Ci0 alkyl group, 3c) a C3-C10 alkenyl group, 4c) a halo C3-C10 alkenyl group, 5c) a C3-C10 alkynyl group, 6c) a halo C3-C10 alkynyl group, 7c) a C3- C10 cycloalkyl group, 8c) a substituted C3-C10 cycloalkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a Ci-C6 alkyl group, and c) a halo Ci-C6 alkyl group, 9c) a C3-C10 cycloalkenyl group, 10c) a substituted C3-C10 cycloalkenyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a Ci-C6 alkyl group, and c) a halo Ci-C6 alkyl group, lie) a C3-C8 cycloalkyl Ci-C6 alkyl group, or 12c) a halo C3-C8 cycloalkyl C1-C6 alkyl group; Z is an oxygen atom or a sulfur atom; X may be the same or different and is Id) a hydrogen atom, 2d) a halogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a Ci~ C6 alkyl group, or 6d) a halo Ci-C6 alkyl group; Y1 is le) a hydrogen atom, 2e) a Ci-C6 alkyl group, 3e) a halo Ci-C6 alkyl group, 4e) a C2-C6 alkenyl group, 5e) a halo C2-Ce alkenyl group, 6e) a C2-C6 alkynyl group, 7e) a halo C2-C6 alkynyl group, 8e) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group, 9e) a hydroxy Ci-C6 alkyl group, lOe) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl group, lie) a C3-C6 cycloalkyl group, 12e) a halo C3-C6 cycloalkyl group, 13e) a C3-C6 cycloalkyl Ci-C6 alkyl group, 14e) a halo C3-C6 cycloalkyl Ci-C6 alkyl group, 15e) a Ci-C6 alkylsulfonyl group, 16e) a halo Ci-C6 alkylsulfonyl group, 17e) a Ci-C6 alkylthio Ci-C6 alkyl group, 18e) a halo C1-C6 alkylthio Ci-C6 alkyl group, 19e) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 20e) a halo Ci-C6 alkylsulf inyl Ci-C6 alkyl group, 21e) a Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 22e) a halo Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 23e) a mono Ci-C6 alkylamino Ci-C6 alkyl group, 24e) a di Ci-C6 alkylamino Ci-C6 alkyl group wherein the alkyl groups are the same or different, 25e) a phenyl group, .2 6e) a substituted phenyl group having, on the ring, one or more, the same or different substituents selected 88 from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group; Y2 may be the same or different and is If) a hydrogen atom, 2f) a halogen atom, 3f) a cyano group, 4f) a nitro group, 5f) a hydroxyl group, 6f) a mercapto group, If) an amino group, 8f) a carboxyl group, 9f) a Ci-C6 alkyl group, lOf) a halo Ci-C6 alkyl group, llf) a C2-C6 alkenyl group, 12f) a halo C2-C6 alkenyl group, 13f) a C2-C6 alkynyl group, 14f) a halo C2-C6 alkynyl group, 15f) a tri Ci-C6 alkylsilyl C2-C6 alkynyl group wherein the alkyl groups are the same or different, 16f) a phenyl C2-C6 alkynyl group, 17f) a Ci-C6 alkoxy Ci-C6 alkoxy Ci- C6 alkyl group, 18f) a hydroxy Ci-C6 alkyl group, 19f) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl group, 20f) a C3-C6 cycloalkyl group, 21f) a halo C3-C6 cycloalkyl group, 22f) a C3-C6 cycloalkyl Ci-Cs alkyl group, 23f) a halo C3-C6 cycloalkyl Ci-C6 alkyl group, 24f) a Ci-C6 alkoxy group, 25f) a halo Ci-C6 alkoxy group, 2 6f) a Ci-C6 alkoxy Ci-C6 alkoxy group, 27f) a halo Ci-C6 alkoxy Ci-C6 alkoxy group, 28f) a phenyl Ci-C6 alkoxy group, 29f) a Ci-C6 alkoxy Ci-C6 alkyl group, 30f) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 31f) a C1-C6 alkylthio group, 32f) a halo Ci- C6 alkylthio group, 33f) a Ci-C6 alkylsulfinyl group, 34f) a halo Ci-C6 alkylsulfinyl group, 35f) a Ci-C6 alkylsulfonyl group, 36f) a halo C1-C6 alkylsulfonyl group, 37f) a Ci-C6 alkylthio Ci-C6 alkyl group, 38f) a halo Ci-C6 alkylthio Ci-C6 alkyl group, 39f) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 40f) a halo Ci-C6 alkylsulfinyl C1-C6 alkyl group, 41f) a C1-C6 alkylsulfonyl C1-C6 alkyl group, 42f) a halo Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 43f) a mono Ci-C6 alkylamino group, 44f) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, 45f) a phenylamino group, 4 6f) a mono Ci-C6 alkylamino Ci-C6 alkyl group, 47f) a di Ci-C6 alkylamino Ci-C5 alkyl group wherein the alkyl groups are the same or different, 48f) a phenyl group, 89 49f) a substituted phenyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 50f) a phenoxy group, 51f) a substituted phenoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Cj.-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 52f) a heterocyclic group, or 53f) a substituted heterocyclic group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-Ce alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group; m is 1 or 2; and n is an integer of 1-3, or a salt thereof. 2. The substituted pyrazolecarboxanilide derivative of claim 1, wherein R1 is la) a hydrogen atom, 2a) a Ci-C6 alkyl group, 3a) a halo Ci-C6 alkyl group, 4a) a Ci-Cs alkylcarbonyl group, 5a) a 90 halo Ci-C5 alkylcarbonyl group, 6a) a C2~C6 alkenylcarbonyl group, 13a) a C2-C6 alkenyl group, 17a) a Ci-Cio alkoxy C1-C6 alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy Ci-C6 alkyl group, 20a) a C1-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group, 29a) a phenyl Ci-C6 alkoxy Ci-C6 alkyl group, 30a) a substituted phenyl Ci-C6 alkoxy Ci-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a Ci-Ci6 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6 alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group, 34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6 alkylthiocarbonyl group, 42a) a phenyl Ci-C6 alkyl group, 43a) a substituted phenyl Ci-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci~C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a substituted phenylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 91 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 4 6a) a heterocyclylcarbonyl group, 47a) a substituted heterocyclylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci~C6 alkylamino group, 0) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C5 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 50a) a phenoxy Ci-C6 alkylcarbonyl group, 51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl 92 group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 58a) a di C1-C6 alkylaminothio group wherein the alkyl groups are the same or different, 59a) a C3-C6 cycloalkylcarbonyl group, 61a) a C1-C6 alkyl C3-C6 cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-Ce alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 68a) a C1-C6 alkoxy C1-C6 alkylcarbonyl group, 73a) a Ci-C6 alkylcarbonyl Ci-C6 alkylcarbonyl group, or 74a) a Ci-C6 alkoxycarbonyl Ci-C6 alkylcarbonyl group, or a salt thereof. 3. The substituted pyrazolecarboxanilide derivative of claim 1 or claim 2, wherein R2 is lb) a hydrogen atom, 2b) a halogen 93 atom, 6b) a hydroxy group, 7b) a Ci-C6 alkoxy group, or 8b) a halo Ci-C6 alkoxy group, or a salt thereof. 4. The substituted pyrazolecarboxanilide derivative of any one of claims 1 to 3, wherein G is lc) a C2-C10 alkyl group, 3c) a C3-C10 alkenyl group, or lie) a C3-C8 cycloalkyl C1-C6 alkyl group, or a salt thereof. 5. The substituted pyrazolecarboxanilide derivative of any one of claims 1 to 4, wherein X is Id) a hydrogen atom, 2d) a halogen atom, or 5d) a Ci-C6 alkyl group, or a salt thereof. 6. The substituted pyrazolecarboxanilide derivative of any one of claims 1 to 5, wherein Z is an oxygen atom; Y1 is 2e) a Ci-C6 alkyl group, 3e) a halo Ci-C6 alkyl group, or 4e) a C2-C6 alkenyl group; and Y2 is If) a hydrogen atom, 2f) a halogen atom, 9f) a Ci-C6 alkyl group, lOf) a halo Ci-C6 alkyl group, or 31f) a Ci-C6 alkylthio group, or a salt thereof. 7. The substituted pyrazolecarboxanilide derivative of claim 1, wherein R1 is la) a hydrogen atom, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo Ci-C6 alkylcarbonyl group, 17a) a C1-C10 alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy C1-C6 alkyl group, *6a) a Ci-Ci6 alkoxycarbonyl group, 3^a) a halo Ci-C6 alkoxycarbonyl group, or 6 group; R2 is lb) a hydrogen atom, or 7b) a C1-C6 alkoxy group; G is lc) a C2-Cij0alkyl group; Z is an oxygen atom; X is Id) a hydrogen atom; Y1 is 2e) a Ci-C6 alkyl group; and Y2 may be the same or different and is If) a hydrogen atom, 2f) a halogen atom, 9f) a Ci-Cs alkyl group, or lOf) a halo C1-C6 alkyl group, 94 or a salt thereof. 8. An agrohorticultural agent comprising a substituted pyrazolecarboxanilide derivative of any one of claims 1 to 7 or a salt thereof as an active ingredient. 9. The agrohorticultural agent of claim 8, which is an agrohorticultural insecticide or acaricide. 10. A method of using an agrohorticultural agent, which comprises treating a target plant or soil with an effective amount of an agrohorticultural agent of claim 8 or 9 so as to control noxious organisms from useful plants. 11. A substituted aniline derivative represented by the formula (II): wherein R1 is la) a hydrogen atom, 2a) a Ci-C8 alkyl group, 3a) a halo C1-C6 alkyl group, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo Ci-C6 alkylcarbonyl group, 6a) a C2~C6 alkenylcarbonyl group, 7a) a halo C2-C6 alkenylcarbonyl group, 8a) a Ci-C6 alkylcarbonyl Ci-C6 alkyl group, 9a) a C3~C6 cycloalkyl group, 10a) a halo C3-C6 cycloalkyl group, 11a) a C3-C6 cycloalkyl Ci-C6 alkyl group, 12a) a halo C3-C6 cycloalkyl C1-C6 alkyl group, 13a) a C2_C6 alkenyl group, 14a) a halo C2-C6 alkenyl group, 15a) a C2-C6 alkynyl group, 16a) a halo C2-C6 alkynyl group, 17a) a Ci-Cio alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy C1-C6 alkyl group, 20a) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group, 21a) a C1-C6 alkylthio C1-C6 alkyl group, 22a) a halo Ci-C6 alkylthio C1-C6 alkyl group, 23a) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 24a) a halo Ci-C6 alkylsulf inyl Ci-C6 alkyl group, 25a) a Ci-C6 alkylsulfonyl Ci-C5 alkyl group, 2 6a) a halo Ci-Cs alkylsulfonyl 95 Ci-C6 alkyl group, 27a) a mono C1-C6 alkylamino Ci-C6 alkyl group, 28a) a di C1-C6 alkylamino Ci-C6 alkyl group wherein the alkyl groups are the same or different, 29a) a phenyl Ci-C6 alkoxy C1-C6 alkyl group, 30a) a substituted phenyl Ci-C6 alkoxy Ci-C5 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-Ce alkyl group, f) a C1-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6 alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group, 34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6 alkylthiocarbonyl group, 36a) a mono Ci-C6 alkylaminocarbonyl group, 37a) a di C1-C6 alkylaminocarbonyl group wherein the alkyl groups are the same or different, 38a) a Ci-C6 alkoxycarbonyl Ci-C6 alkyl group, 39a) a Ci-C6 alkylsulfonyl group, 40a) a halo Ci-C6 alkylsulfonyl group, 41a) a cyano C1-C6 alkyl group, 42a) a phenyl Ci-C6 alkyl group, 43a) a substituted phenyl C1-C6 alkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a substituted phenylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-Cs alkoxy group, h) a C1-C6 alkylthio group, 96 i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a) a substituted heterocyclylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci- C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 50a) a phenoxy Ci-C6 alkylcarbonyl group, 51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a 97 substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 54a) a di Ci-C6 alkylphosphono group wherein the alkyl groups are the same or different, 55a) a di C1-C6 alkylphosphonothio group wherein the alkyl groups are the same or different, 56a) a A/-Ci-C6 alkyl-N-Ci-C6 alkoxycarbonylaminothio group, 57a) a i\7-Ci-C6 alkyl-N-Ci-C6 alkoxycarbonyl Ci-C6 alkylaminothio group, 58a) a di C1-C6 alkylaminothio group wherein the alkyl groups are the same or different, 59a) a C3-C6 cycloalkylcarbonyl group, 60a) a halo C3-C6 cycloalkylcarbonyl group, 61a) a Ci-C6 alkyl C3-C6 cycloalkylcarbonyl group, 62a) a halo Ci-C6 alkyl C3-C6 cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, 98 k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 67a) a C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl group, 69a) a halo C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group, 70a) a phenoxy Ci-C6 alkoxycarbonyl group, 71a) a substituted phenoxy Ci-C6 alkoxycarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci~C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 72a) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl group, 73a) a Ci-C6 alkylcarbonyl Ci-C6 alkylcarbonyl group, or 74a) a Ci-C6 alkoxycarbonyl Ci-C6 alkylcarbonyl group; R2 is lb) a hydrogen atom, 2b) a halogen atom, 3b) a Ci-C6 alkyl group, 4b) a halo Ci-C6 alkyl group, 5b) a cyano group, 6b) a hydroxy group, 7b) a C1-C6 alkoxy group, 8b) a halo C1-C6 alkoxy group, 9b) a Ci-C6 alkoxy C1-C3 alkoxy group, 10b) a halo Ci-C6 alkoxy C1-C3 alkoxy group, lib) a Ci-C6 alkylthio C1-C3 alkoxy group, 12b) a halo Ci-C6 alkylthio C1-C3 alkoxy group, 13b) a Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 14b) a halo Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 15b) a Ci-C6 alkylsulfonyl Ci- C3 alkoxy group, 16b) a halo Ci-C6 alkylsulfonyl C1-C3 alkoxy group, 17b) a mono Ci-C6 alkylamino C1-C3 alkoxy group, 18b) a di Ci-C6 alkylamino C1-C3 alkoxy group wherein the alkyl groups are the same or different, 19b) a Ci-C6 alkylthio group, 20b) a halo Ci-C6 alkylthio group, 21b) a Ci-C6 alkylsulfinyl group, 22b) a halo Ci-C6 alkylsulfinyl group, 23b) a Ci-C6 alkylsulfonyl group, 24b) a halo Ci-C6 alkylsulfonyl group, 25b) an amino group, 2 6b) a mono C1-C6 alkylamino group, 27b) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, 28b) a phenoxy group, 29b) a substituted phenoxy 99 group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group, 30b) a phenylthio group, 31b) a substituted phenylthio group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-Cs alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 32b) a phenylsulfinyl group, 33b) a substituted phenylsulfinyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 34b) a phenylsulfonyl group, 35b) a substituted phenylsulfonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl 100 group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group, 36b) a phenyl Ci-C6 alkoxy group, or 37b) a substituted phenyl Ci-C6 alkoxy group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci- Ce alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di C1-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a Ci-C6 alkoxycarbonyl group; G is lc) a C2-Cio alkyl group, 2c) a halo C2-Cio alkyl group, 3c) a C3-C10 alkenyl group, 4c) a halo C3-C10 alkenyl group, 5c) a C3-C10 alkynyl group, 6c) a halo C3-C10 alkynyl group, 7c) a C3- C10 cycloalkyl group, 8c) a substituted C3-C10 cycloalkyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a Ci-C6 alkyl group, and c) a halo Ci-C6 alkyl group, 9c) a C3-C10 cycloalkenyl group, 10c) a substituted C3-C10 cycloalkenyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a Ci-C6 alkyl group, and c) a halo Ci-C6 alkyl group, lie) a C3-C9 cycloalkyl Ci-C6 alkyl group, or 12c) a halo C3-C8 cycloalkyl Ci-C6 alkyl group; X may be the same or different and is Id) a hydrogen atom, 2d) a halogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a Ci- Ce alkyl group, or 6d) a halo Ci-C6 alkyl group; and n is an integer of 1-3, or a salt thereof. 12. The substituted aniline derivative of claim 11, wherein R1 is la) a hydrogen atom, 2a) a Ci-C6 alkyl group, 3a) a halo Ci- C6 alkyl group, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo Ci~ C6 alkylcarbonyl group, 17a) a Ci-C6 alkoxy Ci-C6 alkyl group, 31 18a) a halo C1-C6 alkoxy Ci-Cs alkyl group, 36 a) a Ci-C(6 101 33 alkoxycarbonyl group, 3£a) a halo Ci-C6 alkoxycarbonyl group, ¥i 45 4 phenylcarbonyl group having, on the ring, one or more, the same or different substituents selected from a) a halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci- C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group wherein the alkyl groups are the same or different, and p) a C1-C6 alkoxycarbonyl group; R2 is lb) a hydrogen atom, 2b) a halogen atom, 6b) a hydroxy group, 7b) a Ci-C6 alkoxy group, or 8b) a halo C1-C6 alkoxy group; G is lc) a C2-Cio alkyl group; and X is Id) a hydrogen atom, or 5d) a Ci-C6 alkyl group, or a salt thereof. 102 13. 1, 3-Dimethyl-5-trifluoromethylpyrazole-4-carboxylic acid or a salt thereof. The substituted pyrazolecarboxanilide derivatives represented by of the formula (I) wherein R1 is H, alkyl, alkylcarbonyl, alkenylcarbonyl, cycloalkyl, phenylalkyl, phenylcarbonyl and the like; R2 is H, halogen, alkyl, CN, OH, alkoxy, phenoxy, phenylthio, phenylsulfonyl and the like; G is alkyl, alkenyl, alkynyl, cycloalkyl, C3-C10 cycloalkenyl and the like; Z is 0 or S; X is H, halogen, CN, NO2, alkyl and the like; Y1 is H, alkyl, alkenyl, phenyl, alkoxyalkyl and the like; Y2 is H, halogen, CN, NO2, OH, mercapto, amino, carboxyl, C1-C6 alkyl, phenyl, phenoxy, heterocycle and the like, m is 1 or 2; and n is 1-3, and salts thereof exhibit a superior effect as agrohorticultural insecticides or acaricides.

Full Text

DESCRIPTION
SUBSTITUTED PYRAZOLECARBOXYLIC ACID ANILIDE DERIVATIVE OR SALT
THEREOF, INTERMEDIATE THEREOF, AGENT FOR AGRICULTURAL AND
HORTICULTURAL USE, AND USE THEREOF
Technical Field
The present invention relates to substituted
pyrazolecarboxanilide derivatives or salts thereof,
intermediates thereof, and agrohorticultural agents,
particularly insecticides or acaricides, containing said
compounds as an active ingredient and method for use thereof.
Background Art
Conventionally, substituted pyrazolecarboxamide
derivatives similar to the present invention are known to be
useful as agrohorticultural insecticides, fungicides or
acaricides (e.g., JP-A-2003-48878, JP-A-2004-189738 and JP-A-
2004-269515). In JP-A-2003-48878, the substituted
pyrazolecarboxanilide derivatives are disclosed. However, the
substituents in the aniline moiety are mostly limited to the
2-position substituents, the 3-position substituent is methyl
group alone, and the compound described in the present
invention, wherein alkyl group having 2 or more carbon atoms
is introduced into the 3-position is not included even in its
compound list. Moreover, the 3-position methyl form concretely
disclosed therein does not show an acaricide activity. In JP-
A-2004-189738, substituted pyrazolecarboxanilide derivatives
are disclosed. However, the substituents in the aniline moiety
are limited to alkoxy group, alkylthio group and alkylamino
group, and the compound described in the present invention,
wherein alkyl group having 2 or more carbon atoms is directly
introduced into the 3-position is not included even in its
compound list. In JP-A-2004-269515, substituted
pyrazolecarboxamide derivatives are disclosed. However, only
an amide compound with heterocyclyl amine is disclosed, and
the substituted pyrazolecarboxanilide derivatives of the
present invention are not disclosed.
Disclosure of the Invention
In crop manufacturing in agricultural and horticultural
fields, damages caused by insect pests are still serious, and
development of novel agrohorticultural agents, particularly
1

development of insecticides and acaricides is desired due to
generation of insect pests resistant to known agents, and the
like. Since various labor saving farm works are required due
to increasing numbers of the aged farm working population,
creation of agrohorticultural agents with properties suitable
for such labor saving farm works, particularly insecticides
and acaricides, is also demanded.
The present inventors have continued extensive studies on
development of novel agrohorticultural agents, particularly
insecticides and acaricides and have found, as the result,
that among broad range of compounds described in the
aforementioned prior document, a substituted
pyrazolecarboxanilide derivative represented by the formula
(I), in which a pyrazole ring is selected as the heterocyclic
carboxylic acid moiety and a specific substituent is
introduced into the aniline moiety at 3-position, showed
excellent control effect as acaricides, not predicted at all
from the content described in the aforementioned prior art
references. Further, the inventors have found that an
intermediate of said compound, i.e. a substituted aniline
derivatives represented by the formula (II), and 1,3-dimethyl-
5-trifluoromethylpyrazole-4-carboxylic acid or salt thereof
were novel compounds unknown in prior references, and were
useful as intermediates for manufacturing various derivatives
having physiological activities such as pharmaceuticals,
pesticides and the like, and thus completed the present
invention.

wherein
R1 is la) a hydrogen atom, 2a) a Ci-C8 alkyl group, 3a) a halo
2
Accordingly, the present invention relates to
substituted pyrazolecarboxanilide derivatives represented by
the formula (I):

Ci-C6 alkyl group, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo
Ci-C6 alkylcarbonyl group, 6a) a C2-C6 alkenylcarbonyl group,
7a) a halo C2-C6 alkenylcarbonyl group, 8a) a Ci-C6
alkylcarbonyl Ci-C6 alkyl group, 9a) a C3-C6 cycloalkyl group,
10a) a halo C3-C6 cycloalkyl group, 11a) a C3-C6 cycloalkyl Ci-C6
alkyl group, 12a) a halo C3-Cs cycloalkyl Ci-C6 alkyl group,
13a) a C2-C6 alkenyl group, 14a) a halo C2-C5 alkenyl group,
15a) a C2-C6 alkynyl group, 16a) a halo C2-C6 alkynyl group,
17a) a Ci-Cio alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy
Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy Ci-C6 alkyl group,
20a) a C1-C6 alkoxy Ci-Cs alkoxy C1-C6 alkyl group, 21a) a Ci-C6
alkylthio Ci-C6 alkyl group, 22a) a halo Ci-C6 alkylthio Ci-C6
alkyl group, 23a) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 24a)
a halo Ci-C6 alkylsulf inyl C1-C6 alkyl group, 25a) a Ci-C6
alkylsulfonyl Ci-C6 alkyl group, 26a) a halo Ci-C6 alkylsulfonyl
C1-C6 alkyl group, 27a) a mono C1-C6 alkylamino C1-C6 alkyl
group, 28a) a di Ci-C6 alkylamino Ci-C6 alkyl group wherein the
alkyl groups are the same or different, 29a) a phenyl Ci-C6
alkoxy Ci-C6 alkyl group, 30a) a substituted phenyl Ci-C6 alkoxy
Ci-Cs alkyl group having, on the ring, one or more, the same or
different substituents selected from a) a halogen atom, b) a
cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6
alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a Ci-C6 alkylsulf inyl group, k) a halo Ci-Cs
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di C1-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a
C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6
alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group,
34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6
alkylthiocarbonyl group, 3 6a) a mono Ci-C6 alkylaminocarbonyl
group, 37a) a di Ci-C6 alkylaminocarbonyl group wherein the
alkyl groups are the same or different, 38a) a Ci-C6
alkoxycarbonyl Ci-C6 alkyl group, 39a) a Ci-C6 alkylsulfonyl
group, 40a) a halo Ci-C6 alkylsulfonyl group, 41a) a cyano Ci-C6
alkyl group, 42a) a phenyl Ci-C6 alkyl group, 43a) a
substituted phenyl Ci-C6 alkyl group having, on the ring, one
3

or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a
substituted phenylcarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a)
a substituted heterocyclylcarbonyl group having, on the ring,
one or more, the same or different substituents selected from
a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci~
C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a
substituted phenoxycarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
4

group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 50a) a phenoxy C1-C6 alkylcarbonyl group,
51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on
the ring, one or more, the same or different substituents
selected from a) a halogen atom, b) a cyano group, c) a nitro
group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a
Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6
alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6
alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a
Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group,
n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a
substituted phenylsulfonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C5
alkoxycarbonyl group, 54a) a di Ci-C6 alkylphosphono group
wherein the alkyl groups are the same or different, 55a) a di
Ci-C6 alkylphosphonothio group wherein the alkyl groups are the
same or different, 56a) a N-Ci-C6 alkyl-N-Ci-C6
alkoxycarbonylaminothio group, 57a) a N-Ci-C6 alkyl-W-Ci-C6
alkoxycarbonyl Ci-C6 alkylaminothio group, 58a) a di Ci-C6
alkylaminothio group wherein the alkyl groups are the same or
different, 59a) a C3-C6 cycloalkylcarbonyl group, 60a) a halo
C3-C6 cycloalkylcarbonyl group, 61a) a C1-C6 alkyl C3-C6
cycloalkylcarbonyl group, 62a) a halo Ci-C6 alkyl C3-C6
cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl
group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano
5

group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6
alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy
group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio
group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a
phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted
phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 67a) a C3-C6 cycloalkyl Ci-C6
alkylcarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl
group, 69a) a halo C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group,
70a) a phenoxy Ci-C6 alkoxycarbonyl group, 71a) a substituted
phenoxy C1-C6 alkoxycarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 72a) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl
group, 73a) a Ci-C6 alkylcarbonyl Ci-Ce alkylcarbonyl group, or
74a) a Ci-C6 alkoxycarbonyl C1-C6 alkylcarbonyl group;
R2 is lb) a hydrogen atom, 2b) a halogen atom, 3b) a Ci-C6 alkyl
group, 4b) a halo Ci-C6 alkyl group, 5b) a cyano group, 6b) a
hydroxy group, 7b) a Ci-C6 alkoxy group, 8b) a halo Ci-C6 alkoxy
6

group, 9b) a Ci-C6 alkoxy C1-C3 alkoxy group, 10b) a halo Ci-C6
alkoxy C1-C3 alkoxy group, lib) a Ci-C6 alkylthio C1-C3 alkoxy
group, 12b) a halo Ci-C6 alkylthio C1-C3 alkoxy group, 13b) a
Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 14b) a halo Ci-C6
alkylsulfinyl C1-C3 alkoxy group, 15b) a Ci-C6 alkylsulfonyl d-
C3 alkoxy group, 16b) a halo C1-C6 alkylsulfonyl C1-C3 alkoxy
group, 17b) a mono Ci-C6 alkylamino C1-C3 alkoxy group, 18b) a
di C1-C6 alkylamino C1-C3 alkoxy group wherein the alkyl groups
are the same or different, 19b) a Ci-C6 alkylthio group, 20b) a
halo Ci-C6 alkylthio group, 21b) a C1-C6 alkylsulfinyl group,
22b) a halo Ci-C6 alkylsulfinyl group, 23b) a Ci-C6
alkylsulfonyl group, 24b) a halo Ci-C6 alkylsulfonyl group,
25b) an amino group, 2 6b) a mono Ci-C6 alkylamino group, 27b) a
di C1-C6 alkylamino group wherein the alkyl groups are the same
or different, 28b) a phenoxy group, 29b) a substituted phenoxy
group having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Cx-C6 alkoxycarbonyl group, 30b) a
phenylthio group, 31b) a substituted phenylthio group having,
on the ring, one or more, the same or different substituents
selected from a) a halogen atom, b) a cyano group, c) a nitro
group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a
Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6
alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6
alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a
Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group,
n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group, 32b) a phenylsulfinyl group, 33b) a
substituted phenylsulfinyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
7

alkyl group, e) a halo C1-C6 alkyl group, f) a C1-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 34b) a phenylsulfonyl group, 35b) a
substituted phenylsulfonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group, 36b) a phenyl C1-C6 alkoxy group, or 37b)
a substituted phenyl Ci-C6 alkoxy group having, on the ring,
one or more, the same or different substituents selected from
a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-
C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group;
G is lc) a C2-Cio alkyl group, 2c) a halo C2-Cio alkyl group, 3c)
a C3-C10 alkenyl group, 4c) a halo C3-C10 alkenyl group, 5c) a
C3-C10 alkynyl group, 6c) a halo C3-C10 alkynyl group, 7c) a C3-
C10 cycloalkyl group, 8c) a substituted C3-C10 cycloalkyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a Ci-C6 alkyl
group, and c) a halo Ci-C6 alkyl group, 9c) a C3-C10
cycloalkenyl group, 10c) a substituted C3-C10 cycloalkenyl group
having, on the ring, one or more, the same or different
8

substituents selected from a) a halogen atom, b) a Ci-C6 alkyl
group, and c) a halo Ci-C6 alkyl group, lie) a C3-C8 cycloalkyl
Ci-C6 alkyl group, or 12c) a halo C3-C8 cycloalkyl Ci-C6 alkyl
group;
Z is an oxygen atom or a sulfur atom;
X may be the same or different and is Id) a hydrogen atom, 2d)
a halogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a Ci-
C6 alkyl group, or 6d) a halo C1-C6 alkyl group;
Y1 is le) a hydrogen atom, 2e) a Ci-C6 alkyl group, 3e) a halo
Ci-C6 alkyl group, 4e) a C2-C6 alkenyl group, 5e) a halo C2-C6
alkenyl group, 6e) a C2-C6 alkynyl group, 7e) a halo C2-Cs
alkynyl group, 8e) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group,
9e) a hydroxy Ci-C6 alkyl group, lOe) a Ci-C6 alkylcarbonyloxy
Ci-C6 alkyl group, lie) a C3-C6 cycloalkyl group, 12e) a halo
C3-C5 cycloalkyl group, 13e) a C3-C6 cycloalkyl Ci-C6 alkyl group,
14e) a halo C3-C6 cycloalkyl Ci-C6 alkyl group, 15e) a Ci-C6
alkylsulfonyl group, 16e) a halo C1-C6 alkylsulfonyl group,
17e) a Ci-C6 alkylthio Ci-C6 alkyl group, 18e) a halo C1-C6
alkylthio Ci-C6 alkyl group, 19e) a Ci-C6 alkylsulfinyl Ci-C6
alkyl group, 20e) a halo C1-C6 alkylsulf inyl Ci-C6 alkyl group,
21e) a Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 22e) a halo Ci-C6
alkylsulfonyl Ci-C6 alkyl group, 23e) a mono Ci-C6 alkylamino
Ci-C6 alkyl group, 24e) a di Ci-C6 alkylamino Ci-C6 alkyl group
wherein the alkyl groups are the same or different, 25e) a
phenyl group, 2 6e) a substituted phenyl group having, on the
ring, one or more, the same or different substituents selected
from a) a halogen atom, b) a cyano group, c) a nitro group, d)
a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6
alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio
group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulf inyl
group, k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6
alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a
mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group;
Y2 may be the same or different and is If) a hydrogen atom, 2f)
a halogen atom, 3f) a cyano group, 4f) a nitro group, 5f) a
hydroxyl group, 6f) a mercapto group, 7f) an amino group, 8f)
a carboxyl group, 9f) a Ci-C6 alkyl group, lOf) a halo Ci-C6
9

alkyl group, llf) a C2-C6 alkenyl group, 12f) a halo C2-C6
alkenyl group, 13f) a C2-C6 alkynyl group, 14f) a halo C2-Cs
alkynyl group, 15f) a tri C1-C6 alkylsilyl C2-C6 alkynyl group
wherein the alkyl groups are the same or different, 16f) a
phenyl C2-C6 alkynyl group, 17f) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-
C6 alkyl group, 18f) a hydroxy Ci-C6 alkyl group, 19f) a Ci-C6
alkylcarbonyloxy Ci-C6 alkyl group, 20f) a C3-C6 cycloalkyl
group, 21f) a halo C3-C6 cycloalkyl group, 22f) a C3-C6
cycloalkyl Ci-C6 alkyl group, 23f) a halo C3-C6 cycloalkyl Ci-C6
alkyl group, 24f) a Ci-C6 alkoxy group, 25f) a halo C1-C6 alkoxy
group, 26f) a Ci-C6 alkoxy Ci-C6 alkoxy group, 27f) a halo Ci-C6
alkoxy Ci-C6 alkoxy group, 28f) a phenyl Ci-C6 alkoxy group,
29f) a Ci-Cs alkoxy Ci-C6 alkyl group, 30f) a halo Ci-C6 alkoxy
Ci-Cg alkyl group, 31f) a Ci-C6 alkylthio group, 32f) a halo Ci~
C6 alkylthio group, 33f) a Ci-C6 alkylsulfinyl group, 34f) a
halo Ci-C6 alkylsulfinyl group, 35f) a Ci-C6 alkylsulfonyl group,
36f) a halo Ci-C6 alkylsulfonyl group, 37f) a Ci-C6 alkylthio
Ci-C6 alkyl group, 38f) a halo Ci-C6 alkylthio Ci-C6 alkyl group,
39f) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 40f) a halo Ci-C6
alkylsulfinyl Ci-C6 alkyl group, 41f) a Ci-C6 alkylsulfonyl Ci-C6
alkyl group, 42f) a halo Ci-C6 alkylsulfonyl C1-C6 alkyl group,
43f) a mono Ci-C6 alkylamino group, 44f) a di Ci-C6 alkylamino
group wherein the alkyl groups are the same or different, 45f)
a phenylamino group, 4 6f) a mono Ci-C6 alkylamino Ci-C6 alkyl
group, 47f) a di C1-C6 alkylamino Ci-C6 alkyl group wherein the
alkyl groups are the same or different, 48f) a phenyl group,
49f) a substituted phenyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci~C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group, 50f) a phenoxy group, 51f) a substituted
phenoxy group having, on the ring, one or more, the same or
different substituents selected from a) a halogen atom, b) a
10

cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo C1-C6 alkyl group, f) a Ci-Cs alkoxy group, g) a halo Ci-C6
alkoxy group, h) a C1-C6 alkylthio group, i) a halo C1-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 52f) a
heterocyclic group, or 53f) a substituted heterocyclic group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group;
m is 1 or 2; and
n is an integer of 1-3,
salts thereof and agrohorticultural agents containing the
compound as an active ingredient, and methods of use thereof.
In addition, the present invention also relates to
substituted aniline derivatives represented by the formula
(II), which are intermediates therefor:

wherein
R1 is la) a hydrogen atom, 2a) a Ci-C8 alkyl group, 3a) a halo
C1-C6 alkyl group, 4a) a C1-C6 alkylcarbonyl group, 5a) a halo
Ci-C6 alkylcarbonyl group, 6a) a C2-C6 alkenylcarbonyl group,
7a) a halo C2-C6 alkenylcarbonyl group, 8a) a Ci-C6
alkylcarbonyl Ci-C6 alkyl group, 9a) a C3-C6 cycloalkyl group,
10a) a halo C3-C6 cycloalkyl group, 11a) a C3-C6 cycloalkyl C1-C6
11

alkyl group, 12a) a halo C3-C6 cycloalkyl Ci-C6 alkyl group,
13a) a C2-C6 alkenyl group, 14a) a halo C2-C6 alkenyl group,
15a) a C2-C6 alkynyl group, 16a) a halo C2-C6 alkynyl group,
17a) a C1-C10 alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy
Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy Ci-C6 alkyl group,
20a) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-Cs alkyl group, 21a) a Ci-C6
alkylthio Ci-C6 alkyl group, 22a) a halo Ci-C6 alkylthio Ci-C6
alkyl group, 23a) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 24a)
a halo Ci-C6 alkylsulf inyl Ci-C6 alkyl group, 25a) a C1-C6
alkylsulfonyl Ci-C6 alkyl group, 2 6a) a halo Ci-C6 alkylsulfonyl
Ci-C6 alkyl group, 27a) a mono Ci-C6 alkylamino Ci-C6 alkyl
group, 28a) a di Ci-C6 alkylamino Ci-C6 alkyl group wherein the
alkyl groups are the same or different, 29a) a phenyl Ci-C6
alkoxy Ci-C6 alkyl group, 30a) a substituted phenyl Ci-C6 alkoxy
Ci-C6 alkyl group having, on the ring, one or more, the same or
different substituents selected from a) a halogen atom, b) a
cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6
alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a C1-C6 alkoxycarbonyl group, 31a) a
C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6
alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group,
34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6
alkylthiocarbonyl group, 3 6a) a mono Ci-C6 alkylaminocarbonyl
group, 37a) a di Ci-C6 alkylaminocarbonyl group wherein the
alkyl groups are the same or different, 38a) a Ci-C6
alkoxycarbonyl Ci-C6 alkyl group, 39a) a Ci-C6 alkylsulfonyl
group, 40a) a halo C1-C6 alkylsulfonyl group, 41a) a cyano Ci-C6
alkyl group, 42a) a phenyl C1-C6 alkyl group, 43a) a
substituted phenyl Ci-C6 alkyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
12

k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a
substituted phenylcarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a)
a substituted heterocyclylcarbonyl group having, on the ring,
one or more, the same or different substituents selected from
a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-
C6 alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a
substituted phenoxycarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6
alkyl group, e) a halo Ci-C5 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 50a) a phenoxy Ci-C6 alkylcarbonyl group,
51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on
13

the ring, one or more, the same or different substituents
selected from a) a halogen atom, b) a cyano group, c) a nitro
group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a
C1-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6
alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6
alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a
Ci-C6 alkylsulfonyl group, m) a halo Ci~C6 alkylsulfonyl group,
n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a
substituted phenylsulfonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 54a) a di Ci-C6 alkylphosphono group
wherein the alkyl groups are the same or different, 55a) a di
Ci-C6 alkylphosphonothio group wherein the alkyl groups are the
same or different, 56a) a N-Ci-C6 alkyl-N-Ci-C6
alkoxycarbonylaminothio group, 57a) a N-C1-C6 alkyl-N-Ci-C6
alkoxycarbonyl Ci-C6 alkylaminothio group, 58a) a di Ci-C6
alkylaminothio group wherein the alkyl groups are the same or
different, 59a) a C3-Cs cycloalkylcarbonyl group, 60a) a halo
C3-C6 cycloalkylcarbonyl group, 61a) a Ci-C6 alkyl C3-C6
cycloalkylcarbonyl group, 62a) a halo Ci-C6 alkyl C3-C6
cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl
group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano
group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6
alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy
group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio
group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
14

Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a
phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted
phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 67a) a C3-C6 cycloalkyl C1-C6
alkylcarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl
group, 69a) a halo C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group,
70a) a phenoxy Ci-C6 alkoxycarbonyl group, 71a) a substituted
phenoxy Ci-C6 alkoxycarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 72a) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl
group, 73a) a Ci-C6 alkylcarbonyl C1-C6 alkylcarbonyl group, or
74a) a Ci-C6 alkoxycarbonyl Ci-C6 alkylcarbonyl group;
R2 is lb) a hydrogen atom, 2b) a halogen atom, 3b) a Ci-C6 alkyl
group, 4b) a halo Ci-C6 alkyl group, 5b) a cyano group, 6b) a
hydroxy group, 7b) a Ci-C6 alkoxy group, 8b) a halo Ci-C6 alkoxy
group, 9b) a Ci-C6 alkoxy C1-C3 alkoxy group, 10b) a halo C1-C6
alkoxy C1-C3 alkoxy group, lib) a C1-C6 alkylthio C1-C3 alkoxy
group, 12b) a halo Ci-C6 alkylthio C1-C3 alkoxy group, 13b) a
Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 14b) a halo Ci-C6
alkylsulfinyl C1-C3 alkoxy group, 15b) a Ci-C6 alkylsulfonyl Ci-
15

C3 alkoxy group, 16b) a halo Ci-C6 alkylsulfonyl C1-C3 alkoxy
group, 17b) a mono Ci-C6 alkylamino C1-C3 alkoxy group, 18b) a
di Ci-C6 alkylamino C1-C3 alkoxy group wherein the alkyl groups
are the same or different, 19b) a Ci-C6 alkylthio group, 20b) a
halo Ci-C6 alkylthio group, 21b) a Ci-C6 alkylsulfinyl group,
22b) a halo Ci-C6 alkylsulfinyl group, 23b) a Ci-C6
alkylsulfonyl group, 24b) a halo Ci-C6 alkylsulfonyl group,
25b) an amino group, 2 6b) a mono C1-C6 alkylamino group, 27b) a
di C1-C6 alkylamino group wherein the alkyl groups are the same
or different, 28b) a phenoxy group, 29b) a substituted phenoxy
group having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-Cs alkylamino group, o) a di C1-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 30b) a
phenylthio group, 31b) a substituted phenylthio group having,
on the ring, one or more, the same or different substituents
selected from a) a halogen atom, b) a cyano group, c) a nitro
group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a
Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h) a Ci-C6
alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6
alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a
Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group,
n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group, 32b) a phenylsulfinyl group, 33b) a
substituted phenylsulfinyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
16

alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 34b) a phenylsulfonyl group, 35b) a
substituted phenylsulfonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulf onyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 36b) a phenyl Ci-C6 alkoxy group, or 37b)
a substituted phenyl Ci-C6 alkoxy group having, on the ring,
one or more, the same or different substituents selected from
a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-
C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group;
G is lc) a C2-Cio alkyl group, 2c) a halo C2-Ci0 alkyl group, 3c)
a C3-C10 alkenyl group, 4c) a halo C3-C10 alkenyl group, 5c) a
C3-C10 alkynyl group, 6c) a halo C3-C10 alkynyl group, 7c) a C3-
C10 cycloalkyl group, 8c) a substituted C3-C10 cycloalkyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a Ci-C6 alkyl
group, and c) a halo Ci-C6 alkyl group, 9c) a C3-C10
cycloalkenyl group, 10c) a substituted C3-C10 cycloalkenyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a Ci-C6 alkyl
group, and c) a halo C1-C6 alkyl group, lie) a C3-C8 cycloalkyl
Ci-C6 alkyl group, or 12c) a halo C3-Ce cycloalkyl Ci-C6 alkyl
group;
X may be the same or different and is Id) a hydrogen atom, 2d)
17

a halogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a Ci-
C6 alkyl group, or 6d) a halo C1-C6 alkyl group;
n is an integer of 1-3,
salts thereof and 1,3-dimethyl-5-trifluoromethylpyrazole-4-
carboxylic acid and a salt thereof.
Best Mode for Embodying the Invention
In the definitions of a substituted pyrazolecarboxanilide
derivative of the formula (I) and a substituted aniline
derivative of the formula (II) of the present invention,
"halo", "Ci-C6 alkyl", "Ci-C6 alkoxyl", "C2-C6 alkenyl", "C2-C6
alkynyl" or "a heterocyclic group", and the like in each of
substituents has the following meaning.
The "halo" or "halogen atom" means a chlorine atom, a
bromine atom, an iodine atom or a fluorine atom.
The "Ci-C6 alkyl" is linear or branched chain alkyl
having 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl,
i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl,
isopentyl, neopentyl, t-pentyl, 2-methylbutyl, 1-ethylpropyl,
n-hexyl, 2-ethylbutyl and the like.
The "Ci-C8 alkyl" is linear or branched chain alkyl
having 1 to 8 carbon atoms, such as methyl, ethyl, n-propyl,
i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl,
isopentyl, neopentyl, t-pentyl, 2-methylbutyl, 1-ethylpropyl,
n-hexyl, 2-ethylbutyl, n-heptyl, n-octyl, 2-ethylhexyl and the
like.
The "C2-C10 alkyl" is linear or branched chain alkyl
having 2 to 10 carbon atoms, such as ethyl, n-propyl, i-propyl,
n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, isopentyl,
neopentyl, t-pentyl, 2-methylbutyl, n-hexyl, 2-ethylbutyl, 1-
ethylpropyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl
and the like.
The "C3-C6 cycloalkyl" is cyclic alkyl having 3 to 6
carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl and the like.
The "C3-Ce cycloalkyl" is cyclic alkyl having 3 to 8
carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl, cyclooctyl and the like.
The "C3-C10 cycloalkyl" is cyclic alkyl having 3 to 10
carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl,
18

cyclohexyl, cyclooctyl, cyclodecyl and the like.
The "C3-C10 cycloalkenyl" is cyclic alkenyl having 3 to 10
carbon atoms, such as cyclopropenyl, cyclobutenyl,
cyclopentenyl, cyclohexenyl, cyclooctenyl, cyclodecenyl and
the like.
The "C1-C3 alkoxy" is alkoxy wherein its alkyl moiety is
linear or branched chain alkyl having 1 to 3 carbon atoms,
such as methoxy, ethoxy, propoxy, isopropoxy and the like.
The "Ci-C6 alkoxy" is alkoxy wherein its alkyl moiety is
the above-mentioned "Ci-C6 alkyl", such as methoxy, ethoxy, n-
propoxy, i-propoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy,
n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, 2-
methylbutoxy, 1-ethylpropoxy, hexyloxy, 2-ethylbutoxy and the
like.
The "C1-C10 alkoxy" is alkoxy wherein its alkyl moiety is
linear or branched chain alkyl having 1 to 10 carbon atoms,
such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy,
isobutoxy, s-butoxy, t-butoxy, n-pentyloxy, isopentyloxy,
neopentyloxy, t-pentyloxy, 2-methylbutoxy, 1-ethylpropoxy,
hexyloxy, 2-ethylbutoxy, n-heptyloxy, n-octyloxy, 2-
ethylhexyloxy, n-nonyloxy, n-decyloxy and the like.
The "C1-C16 alkoxy" is alkoxy wherein its alkyl moiety is
linear or branched chain alkyl having 1 to 16 carbon atoms,
such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy,
isobutoxy, s-butoxy, t-butoxy, n-pentyloxy, isopentyloxy,
neopentyloxy, t-pentyloxy, 2-methylbutoxy, 1-ethylpropoxy,
hexyloxy, 2-ethylbutoxy, n-heptyloxy, n-octyloxy, 2-
ethylhexyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n-
dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy,
n-hexadecyloxy and the like.
The "C2-C6 alkenyl" is linear or branched chain alkenyl
having 2 to 6 carbon atoms, which has at least one double bond,
such as vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-
butenyl, 2-pentenyl, 2-methyl-1-propenyl, 2,4-pentadienyl, 3-
hexenyl and the like.
The "C3-C10 alkenyl" is linear or branched chain alkenyl
having 3 to 10 carbon atoms, which has at least one double
bond, such as 1-butenyl, 2-butenyl, 3-butenyl, 2-pentenyl,
2,4-pentadienyl, 3-hexenyl, 3-heptenyl, 3-octenyl, 3-nonenyl,
19

3-decenyl and the like.
The "C2-C6 alkynyl" is linear or branched chain alkynyl
having 2 to 6 carbon atoms, which has at least one triple bond,
such as ethynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl,
2-pentynyl, 3-hexynyl and the like.
The "C3-C10 alkynyl" is linear or branched chain alkynyl
having 3 to 10 carbon atoms, which has at least one triple
bond, such as 1-butynyl, 2-butynyl, 3-butynyl, 2-pentynyl, 3-
hexynyl, 3-heptynyl, 3-octynyl, 3-nonynyl, 3-decynyl and the
like.
The numbers in "C2-C6", "C3-C10" and the like shows the
range of carbon atom numbers such as 2 to 6 carbon atoms and 3
to 10 carbon atoms.
Moreover, the above-mentioned definitions can apply to
groups wherein the above-mentioned substituents are connected.
For example, "halo C1-C6 alkyl" means linear or branched chain
alkyl group having 1 to 6 carbon atoms, which is substituted
by the same or different one or more halogen atoms, such as
chloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 3-
chloropropyl, 2-chloro-l,1-dimethylethyl, 1-bromo-l-
methylethyl, difluoromethyl, trifluoromethyl, 2,2,2-
trifluoroethyl, perfluorohexyl and the like.
"A heterocyclic group" and "A heterocyclyl" are 5- or 6-
membered heterocyclic groups having one or more hetero atoms
selected from an oxygen atom, a sulfur atom and a nitrogen
atom including, for example, pyridyl group, pyridine-N-oxide
group, pyrimidinyl group, furyl group, tetrahydrofuryl group,
thienyl group, tetrahydrothienyl group, tetrahydropyranyl
group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl
group, oxadiazolyl group, thiazolyl group, isothiazolyl group,
thiadiazolyl group, imidazolyl group, triazolyl group and
pyrazolyl group.
A salt of a substituted pyrazolecarboxanilide derivative
represented by the formula (I) of the present invention
includes a salt of an alkali metal (lithium, sodium, potassium,
etc.); a salt of an alkaline earth metal (calcium, magnesium,
etc.); an ammonium salt; and a salt of an organic amine
(methylamine, triethylamine, diethanolamine, piperidine,
pyridine, etc.), or an acid addition salt. The acid addition
20

salt includes, for example, a carboxylate such as acetate,
propionate, oxalate, trifluoroacetate, benzoate and the like;
a sulfonate such as methanesulfonate,
trifluoromethanesulfonate, p-toluenesulfonate and the like; an
inorganic acid salt such as a hydrochloride, a sulfate, a
nitrate, a carbonate and the like.
In the substituted pyrazolecarboxanilide derivatives
represented by the formula (I) of the present invention, R1 is
preferably la) a hydrogen atom, 2a) a Ci-C6 alkyl group, 3a) a
halo C1-C6 alkyl group, 4a) a Ci-C6 alkylcarbonyl group, 5a) a
halo Ci-C6 alkylcarbonyl group, 6a) a C2-C6 alkenylcarbonyl
group, 13a) a C2-C6 alkenyl group, 17a) a C1-C10 alkoxy Ci-C6
alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 19a) a
C2~C6 alkenyloxy C1-C6 alkyl group, 20a) a Ci-C6 alkoxy Ci-C6
alkoxy Ci-C6 alkyl group, 29a) a phenyl Ci-C6 alkoxy Ci-C6 alkyl
group, 30a) a substituted phenyl C1-C6 alkoxy C1-C6 alkyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a C1-C16
alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6 alkoxycarbonyl
group, 33a) a halo Ci-C6 alkoxycarbonyl group, 34a) a C2-C6
alkenyloxycarbonyl group, 35a) a Ci-C6 alkylthiocarbonyl group,
42a) a phenyl Ci-C6 alkyl group, 43a) a substituted phenyl Ci-C6
alkyl group having, on the ring, one or more, the same or
different substituents selected from a) a halogen atom, b) a
cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a
halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6
alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6
alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
21

same or different, and p) a Ci-C6 alkoxycarbonyl group, 44a) a
phenylcarbonyl group, 45a) a substituted phenylcarbonyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 46a) a
heterocyclylcarbonyl group, 47a) a substituted
heterocyclylcarbonyl group having, on the ring, one or more,
the same or different substituents selected from a) a halogen
atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl
group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g)
a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo
Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo
Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a
halo C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group,
0) a di C1-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 48a) a
phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl
group having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 50a) a phenoxy
Ci-C6 alkylcarbonyl group, 51a) a substituted phenoxy Ci-C6
alkylcarbonyl group having, on the ring, one or more, the same
or different substituents selected from a) a halogen atom, b)
a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6
22

alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 52a) a
phenylsulfonyl group, 53a) a substituted phenylsulfonyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a C1-C6 alkyl group, e) a halo C1-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl
group, n) a mono Ci-Cs alkylamino group, o) a di C1-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 58a) a di Ci-C6
alkylaminothio group wherein the alkyl groups are the same or
different, 59a) a C3-C6 cycloalkylcarbonyl group, 61a) a Ci-C6
alkyl C3-C6 cycloalkylcarbonyl group, 63a) a phenyl Ci-C6
alkylcarbonyl group, 64a) a substituted phenyl Ci-C6
alkylcarbonyl group having, on the ring, one or more, the same
or different substituents selected from a) a halogen atom, b)
a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo Ci-C6 alkyl group, f) a Ci~C6 alkoxy group, g) a halo Ci-C6
alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-Cs
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a
phenyl C3~C6 cycloalkylcarbonyl group, 66a) a substituted
phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-Cs alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
23

group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl
group, 73a) a Ci-C6 alkylcarbonyl Ci-Cs alkylcarbonyl group, or
74a) a Ci-C6 alkoxycarbonyl Ci-C6 alkylcarbonyl group, and more
preferably la) a hydrogen atom, 4a) a Ci-C6 alkylcarbonyl group,
5a) a halo Ci-C6 alkylcarbonyl group, 17a) a Ci-Cio alkoxy Ci-C6
3alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, ^Oa) a
C1-C16 alkoxycarbonyl group,, ^?a) a halo Ci-C6 alkoxycarbonyl
group or 6 R2 is preferably lb) a hydrogen atom, 2b) a halogen atom,
6b) a hydroxy group, 7b) a Ci-C6 alkoxy group or 8b) a halo Ci-
C6 alkoxy group, and more preferably lb) a hydrogen atom or 7b)
a Ci-C6 alkoxy group.
G is preferably lc) a C2-Ci0 alkyl group, 3c) a C3-C10
alkenyl group, or lie) a C3-C8 cycloalkyl Ci-C6 alkyl group, and
more preferably lc) a C2-Cio alkyl group.
X is preferably Id) a hydrogen atom, 2d) a halogen atom,
or 5d) a Ci-C6 alkyl group, and more preferably Id) a hydrogen
atom.
Z is preferably an oxygen atom.
Y1 is preferably 2e) a Ci-C6 alkyl group, 3e) a halo Ci-C6
alkyl group, or 4e) a C2-C6 alkenyl group, and more preferably
2e) a Ci-C6 alkyl group.
Y2 is preferably If) a hydrogen atom, 2f) a halogen atom,
9f) a Ci-C6 alkyl group, lOf) a halo Ci-C6 alkyl group, or 31f)
a Ci-C6 alkylthio group, and more preferably If) a hydrogen
atom, 2f) a halogen atom, 9f) a Ci-C6 alkyl group, or lOf) a
halo Ci-C6 alkyl group.
m is preferably 2.
In addition, a salt of a substituted aniline derivative
represented by the formula (II) is preferably an acid addition
salt including, for example, a carboxylate such as acetate,
propionate, oxalate, trifluoroacetate, benzoate and the like;
a sulfonate such as methanesulfonate,
trifluoromethanesulfonate, p-toluenesulfonate and the like; an
inorganic acid salt such as a hydrochloride, a sulfate, a
nitrate, a carbonate and the like.
24

A salt of 1,3-dimethyl-5-trifluoromethylpyrazole-4-
carboxylic acid of the present invention includes a salt of an
alkali metal (lithium, sodium, potassium, etc.); a salt of an
alkaline earth metal (calcium, magnesium, etc.); an ammonium
salt; and a salt of an organic amine (methylamine,
triethylamine, diethanolamine, piperidine, pyridine, etc.).
A substituted pyrazolecarboxanilide derivative
represented by the formula (I) or an intermediate thereof, i.e.
a substituted aniline derivative represented by the formula
(II), of the present invention may contain one or plural
numbers of asymmetric centers in the structural formula, and
further two or more optical isomers and diastereomers may be
present. Consequently, the present invention entirely
encompasses each optical isomer and the mixtures with any
ratio thereof. In addition, a substituted
pyrazolecarboxanilide derivative represented by the formula
(I) of the present invention may have two types of geometric
isomers derived from a C-C double bond in the structural
formula. The present invention encompasses all of geometric
isomers and the mixtures containing them in any ratio.
Moreover, the present invention encompasses hydrates thereof.
Representative production methods for a substituted
pyrazolecarboxanilide derivative represented by the formula
(I) and a substituted aniline derivative represented by the
formula (II), as an intermediate thereof are illustrated
hereinbelow, but the present invention should not be construed
as limiting thereto.
25

(wherein G, R1, X, n, Y1, Y2 and m are as defined above; and R3
is a hydrogen atom, a Ci-C6 alkyl group, a halo Ci-C6 alkyl
group, a phenyl group, a substituted phenyl group or a phenyl
C1-C4 alkyl group; W is -0-, -S- or -N(R4)-, wherein R4 is a
hydrogen atom, a C1-C6 alkyl group, a halo Ci-C6 alkyl group, a
phenyl group, a substituted phenyl group or a phenyl C1-C4
alkyl group; and Q is a halogen atom or a Ci-C6 alkoxyl group) .
Among a substituted pyrazolecarboxanilide derivative
represented by the formula (I), a substituted
pyrazolecarboxanilide derivative (1-1) wherein Z is O, and R2
is a hydrogen atom, a fluorine atom or WR3 wherein W and R3 are
as defined above can be produced by reacting an aniline
derivative represented by the formulas (II-l) to (II-3) with a
pyrazolecarboxylic halide or a pyrazolecarboxylate ester
represented by the formula (III) in the presence or absence of
a base in an inert solvent, or by reacting an aniline
derivative represented by the formulas (II-l) to (II-3) with a
pyrazolecarboxylic acid represented by the formula (IV) in the
presence of a condensing agent, in the presence or absence of
a base, in an inert solvent, and any usual production methods
for amides may be applicable.
An aniline derivative represented by the formula (II-2)
can be produced by reducing an aniline derivative represented
by the formula (II-l) in the presence of a reducing agent, in
an inert solvent.
An aniline derivative represented by the formula (II-3)
26

can be produced by reacting an aniline derivative represented
by the formula (II-l) with an alcohol derivative, a thiol
derivative or an amine derivative represented by the formula
(V), in the presence or absence of a base in an inert solvent.
The formula (II-l) -> the formula (II-2)
An example of a reducing agent to be used in the present
reaction includes metal hydrides such as lithium aluminum
hydride, lithium borohydride, sodium borohydride, diisobutyl
aluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride
and the like, metal such as lithium and the like or metal
salts, and the like. The amount of the reducing agent to be
used may be selected, as appropriate, in the range from
equivalent to excess amount relative to an aniline derivative
represented by the formula (II-l).
An example of an inert solvent to be used in the present
reaction, which may be any one as long as it does not
significantly inhibit progress of the present reaction,
includes aromatic hydrocarbons such as benzene, toluene,
xylene and the like; halogenated hydrocarbons such as
methylene chloride, chloroform, carbon tetrachloride and the
like; halogenated aromatic hydrocarbons such as chlorobenzene,
dichlorobenzene and the like; straight chain or cyclic ethers
such as diethyl ether, dioxane, tetrahydrofuran and the like,
or dimethylsulfoxide and the like and these inert solvents can
be used alone or in combination of two or more kinds.
Reaction temperature may be in the range from room
temperature to boiling temperature of an inert solvent to be
used and reaction time may be in the range from several
minutes to 50 hours, while depending on reaction scale and
reaction temperature.
After completion of the reaction, desired compound may be
isolated from the reaction mixture by a conventional method
and the desired compound can be produced by purification using
recrystallization or column chromatography, etc, if necessary.
The desired compound may also be subjected to subsequent
reaction step without isolation from the reaction mixture.
27

The formula (II-l) -> the formula (II-3)
An example of a base to be used in the present reaction
includes metal hydrides such as lithium hydride, sodium
hydride, potassium hydride and the like; metal alcoholates
such as sodium methoxide, sodium ethoxide, potassium tert-
butoxide and the like; and alkyl metals such as n-butyl
lithium, sec-butyl lithium, tert-butyl lithium and the like.
The amount of the base to be used may be selected, as
appropriate, in the range from equivalent to excess amount
relative to an aniline derivative represented by the formula
(II-D •
As an example of an inert solvent to be used in the
present reaction, which may be any one as long as it does not
significantly inhibit progress of the present reaction,
includes aromatic hydrocarbons such as benzene, toluene,
xylene and the like; alcohols such as methanol, ethanol and
the like; straight chain or cyclic ethers such as diethyl
ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran and the
like, and the like and these inert solvents can be used alone
or in combination of two or more kinds.
Reaction temperature may be in the range from -70°C to
boiling temperature of an inert solvent to be used and
reaction time may be in the range from several minutes to 50
hours, while depending on reaction scale and reaction
temperature.
After completion of the reaction, desired compound may be
isolated from the reaction mixture by a conventional method
and the desired compound can be produced by purification using
recrystallization or column chromatography, etc, if necessary.
The desired compound may also be subjected to subsequent
reaction step without isolation from the reaction mixture.
The formula (II-l), (II-2) or (II-3) -> the formula (1-1)
An example of a condensing agent to be used in the
present reaction includes diethyl cyanophosphate (DEPC),
carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC),
chloroformates, 2-chloro-l-methylpyridinium iodide and the
like.
As a base to be used in the present reaction, an
inorganic base or an organic base is included and an example
28

of an inorganic base includes alkali metal hydroxides such as
sodium hydroxide, potassium hydroxide and the like; alkali
metal hydrides such as sodium hydride, potassium hydride and
the like; alkali metal salts of alcohol such as sodium
ethoxide, potassium tert-butoxide and the like; carbonates
such as sodium carbonate, potassium carbonate, sodium hydrogen
carbonate and the like; and an example of organic bases
includes triethylamine, pyridine, DBU and the like. The amount
of the base to be used may be selected in the range from
equivalent to excess amount relative to a pyrazolecarboxylic
acid derivative represented by the formula (III) or (IV) .
An example of an inert solvent to be used in the present
reaction, which may be any one as long as it does not
significantly inhibit progress of the present reaction,
includes aromatic hydrocarbons such as benzene, toluene,
xylene and the like; halogenated hydrocarbons such as
methylene chloride, chloroform, carbon tetrachloride and the
like; halogenated aromatic hydrocarbons such as chlorobenzene,
dichlorobenzene and the like; straight chain or cyclic ethers
such as diethyl ether, dioxane, tetrahydrofuran and the like;
esters such as ethyl acetate and the like; amides such as
dimethylformamide, dimethylacetamide and the like;
dimethylsulfoxide; 1,3-dimethyl-2-imidazolidinone; acetone,
methyl ethyl ketone and the like. These inert solvents can be
used alone or in combination of two or more kinds.
As the present reaction is an equimolar reaction, each
reactant may be used in equal mole, however, any of the
reactants may also be used in excess. Reaction temperature may
be in the range from room temperature to boiling temperature
of an inert solvent to be used and reaction time may be in the
range from several minutes to 48 hours, while depending on
reaction scale and reaction temperature.
After completion of the reaction, desired compound may be
isolated from the reaction mixture by a conventional method
and the desired compound can be produced by purification using
recrystallization or column chromatography, etc, if necessary.
An aniline derivative represented by the formula (II-l),
as a raw material of the present reaction, can be produced in
accordance with a production method disclosed in JP-A-11-
29

302233, JP-A-2001-122836 or JP-A-2006-8675.
A pyrazolecarboxylic acid derivative represented by the
formulas (III) or (IV) can be produced in accordance with
several methods described in known literatures (for example,
Aust. J. Chem., 1983, 36, 135-147, Synthesis, 1986, 753-755,
JP-A-52-87168, JP-A-63-45264, JP-A-1-106866 and the like).

(wherein G, R1, R2, X, n, Y1, Y2 and m are as defined above) .
Among substituted pyrazolecarboxanilide derivatives
represented by the formula (I), a substituted
pyrazolecarboxanilide derivative (1-2) wherein Z is S can be
produced by reacting an anilide derivative represented by (I-
1) with Lawesson's Reagent in accordance with a known method
(Tetrahedron Lett., 21 (42), 4061 (1980)).

(wherein G, R2, X, n, Y1, Y2, m and Q are as defined above and
R1' is as defined above except a hydrogen atom).
Among substituted pyrazolecarboxanilide derivatives
represented by the formula (I), a substituted
pyrazolecarboxanilide derivative (1-4) wherein R1 is other than
a hydrogen atom can be produced by reacting an amide
derivative represented by the formula (1-3) with a halide
derivative or an ester derivative represented by the formula
(VI) , in the presence or absence of a base, in an inert
30

solvent.
As an example of a base to be used in the present
reaction includes metal hydroxides such as sodium hydroxide,
potassium hydroxide and the like; carbonates such as sodium
carbonate, potassium carbonate, sodium hydrogen carbonate and
the like; metal hydrides such as lithium hydride, sodium
hydride, potassium hydride and the like; metal alcoholates
such as sodium methoxide, sodium ethoxide, potassium tert-
butoxide and the like; alkyl metals such as n-butyl lithium,
sec-butyl lithium, tert-butyl lithium and the like. The amount
of the base to be used may be selected, as appropriate, in the
range from equivalent to excess amount relative to an amide
derivative represented by the formula (1-3).
An example of an inert solvent to be used in the present
reaction, which may be any one as long as it does not
significantly inhibit progress of the present reaction,
includes aromatic hydrocarbons such as benzene, toluene,
xylene and the like; alcohols such as methanol, ethanol and
the like; straight chain or cyclic ethers such as diethyl
ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran and the
like; amides such as dimethylformamide, dimethylacetamide and
the like; dimethylsulfoxide; 1,3-dimethyl-2-imidazolidinone
and the like. These inert solvents can be used alone or in
combination of two or more kinds.
Reaction temperature may be in the range from -70°C to
boiling temperature of an inert solvent to be used and
reaction time may be in the range from several minutes to 50
hours, while depending on reaction scale and reaction
temperature.
After completion of the reaction, desired compound may be
isolated from the reaction mixture by a conventional method
and the desired compound can be produced by purification using
recrystallization or column chromatography, etc, if necessary.
31

(wherein G, R1, R3, X, n, Y1, Y2 and m are as defined above, and
q is 1 or 2).
A substituted pyrazolecarboxanilide derivatives
represented by the formula (1-6) can be produced by reacting a
sulfide derivative represented by the formula (1-5) which can
be produced in Production method 1 with an oxidizing agent in
the presence of an inert solvent
An example of an inert solvent to be used in the present
reaction includes halogenated hydrocarbons such as methylene
chloride, chloroform and the like; aromatic hydrocarbons such
as toluene, xylene and the like; halogenated aromatic
hydrocarbons such as fluorobenzene, chlorobenzene,
dichlorobenzene and the like; acids such as acetic acid and
the like; alcohols such as methanol, ethanol, propanol and the
like.
An example of an oxidizing agent includes m-
peroxychlorobenzoic acid, peracetic acid, potassium
metaperiodate, potassium hydrogen persulphate (Oxone),
hydrogen peroxide and the like. The amount of the oxidizing
agent to be used may be selected, as appropriate, in the range
of 0.5 to 3 equivalents relative to a sulfide derivative
represented by the formula (1-5).
Reaction temperature may be in the range from -50°C to
boiling temperature of an inert solvent to be used and
reaction time may be in the range from several minutes to 24
hours, while depending on reaction scale and reaction
temperature.
After completion of the reaction, desired compound may be
isolated from the reaction mixture by a conventional method
and the desired compound can be produced by purification using
recrystallization or column chromatography, etc, if necessary.
32

Typical compounds of substituted pyrazolecarboxanilide
derivatives represented by the formula (I) are exemplified in
Table 1 and Table 2, and typical compounds of substituted
aniline derivatives represented by the formula (II) are
exemplified in Table 3, and an substituted pyrazolecarboxylic
acid derivative represented by the formula (IV) is exemplified
in Table 4, however, the present invention should not be
construed as limiting to these.
In "property" column of Table 1 and Table 2, melting
point (°C) or refractive index (nD(°C)) is shown and for
compounds described as amorphous or paste, """H-NMR data thereof
were shown in Table 5. In the Tables, "n-" is normal, and "i-"
is iso, "t-" is tertiary, "c-" is cyclo, "Me" is a methyl
group, "Et" is an ethyl group, "Pr" is a propyl group, "Bu" is
a butyl group, "Pen" is a pentyl group, "Hex" is a hexyl group,
"Ph" is a phenyl group, "Bn" is a benzyl group, "Ac" is an
acetyl group and "Pyr" is a pyrazinyl group.
33

Table 1 (Xn=H)
No. G Y1 Y2
1 m R1 R2 Property
1-1 Et Me 3, 5-Me2 H H 72-75
1-2 Et Me 3, 5-Me2 Ac H
1-3 Et Me 3, 5-Me2 H OMe 129-131
1-4 Et Me 3, 5-Me2 Ac OMe 1.5028(25.4)
1-5 Et Me 3; 5-Me2 COEt OMe
1-6 Et Me 3, 5-Me2 CO-c-Pr OMe 118.8-121.6
1-7 Et Me 3, 5-Me2 CH2OMe OMe
1-8 Et Me 3, 5-Me2 CH2OEt OMe 1.4889(24.2)
1-9 Et Me 3, 5-Me2 COOMe OMe
1-10 Et Me 3 5-Me2 COOEt OMe 77.2-79.2
1-11 Et Me 3, 5-Me2 COO-n-Pr OMe
1-12 Et Me 3 5-Me2 COO-i-Bu OMe 1.4895(25.4)
1-13 Et Me 3 5-Me2 H OEt 110-113
1-14 Et Me 3 5-Me2 Ac OEt
1-15 Et Me 3 , 5-Me2 COEt OEt 90-91
1-16 Et Me 3 , 5-Me2 CO-c-Pr OEt 119-120
1-17 Et Me 3 , 5-Me2 CH2OMe OEt
1-18 Et Me 3 , 5-Me2 CH2OEt OEt
1-19 Et Me 3 , 5-Me2 COOMe OEt
1-20 Et Me 3 , 5-Me2 COOEt OEt
1-21 Et Me 3 , 5-Me2 COO-n-Pr OEt
1-22 Et Me 3 , 5-Me2 COO-i-Bu OEt
1-23 Et Me 3- ZF3-5-Me H H 1.4768(21.8)
34

Table 1 (continued)

No. G Y1 Y2 R1 R2 Property
1-24 Et Me 3-CF3-5-Me Ac H 132-134
1-25 Et Me 3-CF3-5-Me H OMe 57-60
1-26 Et Me 3-CF3-5-Me Ac OMe 1.4736(24.6)
1-27 Et Me 3-CF3-5-Me COEt OMe 134-135
1-28 Et Me 3-CF3-5-Me CO-c-Pr OMe 1.4830(26.2)
1-29 Et Me 3-CF3-5-Me CH2OMe OMe
1-30 Et Me 3-CF3-5-Me CH2OEt OMe
1-31 Et Me 3-CF3-5-Me COOMe OMe 128-130
1-32 Et Me 3-CF3-5-Me COOEt OMe 1.4697(25.9)
1-33 Et Me 3-CF3-5-Me COO-n-Pr OMe
1-34 Et Me 3-CF3-5-Me COO-i-Bu OMe 1.4681(26.2)
1-35 Et Me 3-CF3-5-Me H OEt 142-145
1-36 Et Me 3-CF3-5-Me Ac OEt 1.4720(24.5)
1-37 Et Me 3-CF3-5-Me COEt OEt 1.4710(26.9)
1-38 Et Me 3-CF3-5-Me CO-c-Pr OEt
1-39 Et Me 3-CF3-5-Me CH2OMe OEt
1-40 Et Me 3-CF3-5-Me CH2OEt OEt
1-41 Et Me 3-CF3-5-Me COOMe OEt
1-42 Et Me 3-CF3-5-Me COOEt OEt
1-43 Et Me 3-CF3-5-Me COO-n-Pr OEt
1-44 Et Me 3-CF3-5-Me COO-i-Bu OEt
1-45 n-Pr Me 3, 5-Me2 H H 167-168
1-46 n-Pr Me 3, 5-Me2 Ac H
1-47 n-Pr Me 3, 5-Me2 H OMe 184-185
1-48 n-Pr Me 3, 5-Me2 Ac OMe 1.4953(25.0)
1-49 n-Pr Me 3, 5-Me2 COEt OMe 1.4982 (34.2)
1-50 n-Pr Me 3, 5-Me2 CO-c-Pr OMe
1-51 n-Pr Me 3, 5-Me2 CH2OMe OMe 1.4979(22.1)
1-52 n-Pr Me 3, 5-Me2 CH2OEt OMe 1.4942 (22.7)
35

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-53 n-Pr Me 3, 5-Me2 COOMe OMe 1.4980(22.7)
1-54 n-Pr Me 3, 5-Me2 COOEt OMe 1.4952(23.0)
1-55 n-Pr Me 3, 5-Me2 COO-n-Pr OMe
1-56 n-Pr Me 3, 5-Me2 COO-i-Bu OMe 1.4933(23.2)
1-57 n-Pr Me 3, 5-Me2 H OEt 178-179
1-58 n-Pr Me 3, 5-Me2 Ac OEt
1-59 n-Pr Me 3, 5-Me2 COEt OEt 1.4980(22.7)
1-60 n-Pr Me 3, 5-Me2 CO-c-Pr OEt
1-61 n-Pr Me 3, 5-Me2 CH2OMe OEt
1-62 n-Pr Me 3, 5-Me2 CH2OEt OEt
1-63 n-Pr Me 3, 5-Me2 COOMe OEt
1-64 n-Pr Me 3, 5-Me2 COOEt OEt
1-65 n-Pr Me 3, 5-Me2 COO-n-Pr OEt
1-66 n-Pr Me 3, 5-Me2 COO-i-Bu OEt
1-67 n-Pr Me 3-CF3-5-Me H H 131-133
1-68 n-Pr Me 3-CF3-5-Me Ac H
1-69 n-Pr Me 3-CF3-5-Me H OMe 124
1-70 n-Pr Me 3-CF3-5-Me Ac OMe 1.4711(25.6)
1-71 n-Pr Me 3-CF3-5-Me COEt OMe 1.4700(26.8)
1-72 n-Pr Me 3-CF3-5-Me CO-c-Pr OMe 1.4795(25.5)
1-73 n-Pr Me 3-CF3-5-Me CH2OMe OMe
1-74 n-Pr Me 3-CF3-5-Me CH2OEt OMe 1.4658(26.9)
1-75 n-Pr Me 3-CF3-5-Me COOMe OMe 126-128
1-76 n-Pr Me 3-CF3-5-Me COOEt OMe 1.4671 (26.9)
1-77 n-Pr Me 3-CF3-5-Me COO-n-Pr OMe
1-78 n-Pr Me 3-CF3-5-Me COO-i-Bu OMe 1.4645(26.9)
1-79 n-Pr Me 3-CF3-5-Me H OEt
1-80 n-Pr Me 3-CF3-5-Me Ac OEt
1-81 n-Pr Me 3-CF3-5-Me COEt OEt
36

Table 1 (continued)
No. G Y1 Y2
J- m R1 R2 Property
1-82 n-Pr Me 3-CF3-5-Me CO-c-Pr OEt
1-83 n-Pr Me 3-CF3-5-Me CH20Me OEt
1-84 n-Pr Me 3-CF3-5-Me CH20Et OEt
1-85 n-Pr Me 3-CF3-5-Me COOMe OEt
1-86 n-Pr Me 3-CF3-5-Me COOEt OEt
1-87 n-Pr Me 3-CF3-5-Me COO-n-Pr OEt
1-88 n-Pr Me 3-CF3-5-Me COO-i-Bu OEt
1-89 n-Bu Me 3, 5-Me2 H H 150-151.5
1-90 n-Bu Me 3, 5-Me2 Ac H
1-91 n-Bu Me 3, 5-Me2 H OMe 196-197
1-92 n-Bu Me 3, 5-Me2 Ac OMe
1-93 n-Bu Me 3, 5-Me2 H OEt
1-94 n-Bu Me 3, 5-Me2 Ac OEt
1-95 n-Bu Me 3-CF3-5-Me H H 83-85
1-96 n-Bu Me 3-CF3-5-Me Ac H
1-97 n-Bu Me 3-CF3-5-Me H OMe
1-98 n-Bu Me 3-CF3-5-Me Ac OMe
1-99 n-Bu Me 3-CF3-5-Me H OEt
1-100 n-Bu Me 3-CF3-5-Me Ac OEt
1-101 i-Bu Me 3-Me H H 141-144
1-102 i-Bu Me 3-Me Et OMe 1.4916(23.7)
1-103 i-Bu Me 3-Me Ac OMe 1.4961(26.4)
1-104 i-Bu Me 3-Me COEt OMe 1.4973(26.2)
1-105 i-Bu Me 3-Me CO-c-Pr OMe 1.5014(25.5)
1-106 i-Bu Me 3-Me C0(4-Me-Ph) OMe amorphous
1-107 i-Bu Me 3-Me CO(4-N02-Ph) OMe amorphous
1-108 i-Bu Me 3-Me COOMe OMe 95.5-97.8
1-109 i-Bu Me 3-Me COOEt OMe 84.6-86.2
1-110 i-Bu Me 3-Me COO-n-Pr OMe 86.7-88.4
37

Table 1 (continued)
No. G Y1 Y2
J- m R1 R2 Property
1-111 i-Bu Me 3-Me COO-i-Bu OMe 91.8-94.0
1-112 i-Bu Me 3-Me CH2OMe OMe 1.4919(24.0)
1-113 i-Bu Me 3-Me CH2OEt OMe 1.4920(24.4)
1-114 i-Bu Me 3-CF3 H H 172-174
1-115 i-Bu Me 3-CF3 Ac H
1-116 i-Bu Me 3-CF3 H OMe amorphous
1-117 i-Bu Me 3-CF3 Ac OMe
1-118 i-Bu Me 3-CF3 H OEt
1-119 i-Bu Me 3-CF3 Ac OEt
1-120 i-Bu Et 3-CF3 H H 175-176
1-121 i-Bu Me 5-CF3 H H 155-156
1-122 i-Bu Me 5-SMe H H 107-110
1-123 i-Bu Me 3, 5-Me2 H H 148-151
1-124 i-Bu Me 3, 5-Me2 S02(4-F-Ph) H amorphous
1-125 i-Bu Me 3, 5-Me2 Ac H 1.5021(22.5)
1-126 i-Bu Me 3, 5-Me2 COEt H 143.1-148.8
1-127 i-Bu Me 3, 5-Me2 COPh H 51.3-65.3
1-128 i-Bu Me 3, 5-Me2 COCH2CMe3 H 1.4859(22.0)
1-129 i-Bu Me 3, 5-Me2 CH2OEt H 1.4882(23.8)
1-130 i-Bu Me 3, 5-Me2 CH20(CH2)7Me H 1.4854(22.0)
1-131 i-Bu Me 3, 5-Me2 CH20(CH2)2OMe H 1.4889(21.9)
1-132 i-Bu Me 3, 5-Me2 CH2OBn H 1.5212 (21.9)
1-133 i-Bu Me 3, 5-Me2 COOCH2Cl H 121.1-124.8
1-134 i-Bu Me 3, 5-Me2 COOCH2CCl3 H 143.1-145.6
1-135 i-Bu Me 3, 5-Me2 COO(CH2)2CH2Cl H 117.1-121.4
1-136 i-Bu Me 3, 5-Me2 COO-i-Bu H 122.2-138.0
1-137 i-Bu Me 3, 5-Me2 COO-t-Bu H 39.2
1-138 i-Bu Me 3, 5-Me2 COO(CH2)2OMe H 1.4750(23.5)
1-139 i-Bu Me 3, 5-Me2 COO(CH2)15Me H 90.5-92.1
38

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-140 i-Bu Me 3, 5-Me2 Ac OMe 1.5016(23.3)
1-141 i-Bu Me 3/ 5-Me2 COEt OMe 1.4981(23.5)
1-142 i-Bu Me 3, 5-Me2 CO-i-Pr OMe 82.5-83
1-143 i-Bu Me 3, 5-Me2 COPh OMe 1.5219(23.7)
1-144 i-Bu Me 3, 5-Me2 CH2OMe OMe 1.4944(23.1)
1-145 i-Bu Me 3, 5-Me2 CH2OEt OMe 1.4892(22.2)
1-146 i-Bu Me 3/ 5-Me2 CH20(CH2)2OMe OMe 1.4885(25.1)
1-147 i-Bu Me 3, 5-Me2 COOMe OMe 1.4926(23.2)
1-148 i-Bu Me 3, 5-Me2 COOEt OMe 1.4894(23.2)
1-149 i-Bu Me 3, 5-Me2 COOCH2Cl OMe 1.4941(21.5)
1-150 i-Bu Me 3/ 5-Me2 COO-n-Pr OMe 1.4928(22.2)
1-151 i-Bu Me 3, 5-Me2 COO-i-Pr OMe 1.4884(23.0)
1-152 i-Bu Me 3, 5-Me2 COO-i-Bu OMe 1.4829(22.3)
1-153 i-Bu Me 3/ 5-Me2 COOCH2CMe3 OMe 1.4864(23.0)
1-154 i-Bu Me 3, 5-Me2 COO(CH2)2OMe OMe 1.4959(23.0)
1-155 i-Bu Me 3 5-Me2 H OMe 189-190
1-156 i-Bu Me 3 , 5-Me2 Et OMe amorphous
1-157 i-Bu Me 3 , 5-Me2 CH2CC13 OMe 1.4939(22.2)
1-158 i-Bu Me 3 , 5-Me2 Ac OEt 1.4940(26.4)
1-159 i-Bu Me 3 , 5-Me2 COEt OEt 1.4921 (26.5)
1-160 i-Bu Me 3 , 5-Me2 CO-i-Pr OEt paste
1-161 i-Bu Me 3 , 5-Me2 COPh OEt
1-162 i-Bu Me 3 , 5-Me2 CH2OMe OEt
1-163 i-Bu Me 3 , 5-Me2 CH2OEt OEt
1-164 i-Bu Me 3 , 5-Me2 CH20(CH2)2OMe OEt
1-165 i-Bu Me 3 , 5-Me2 COOMe OEt
1-166 i-Bu Me 3 , 5-Me2 COOEt OEt
1-167 i-Bu Me 3 , 5-Me2 COOCH2Cl OEt
1-168 i-Bu Me 3 , 5-Me2 COO-n-Pr OEt
39

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-169 i-Bu Me 3, 5-Me2 COO-i-Pr OEt
1-170 i-Bu Me 3, 5-Me2 COO-i-Bu OEt
1-171 i-Bu Me 3, 5-Me2 COOCH2CMe3 OEt
1-172 i-Bu Me 3, 5-Me2 COO(CH2)2OMe OEt
1-173 i-Bu Me 3, 5-Me2 H OEt 165-166
1-174 i-Bu Me 3, 5-Me2 Et OEt
1-175 i-Bu Me 3, 5-Me2 CH2CC13 OEt
1-176 i-Bu Et 3, 5-Me2 H H 127-128
1-177 i-Bu Me 3, 5-Me2 H F 136.5-137.5
1-178 i-Bu Me 3, 5-Me2 Et H 1.4904(25.7)
1-179 i-Bu Me 3-Me-5-F H H 169.5-171
1-180 i-Bu Me 3-Me-5-F H OMe 135-137
1-181 i-Bu Me 3-Me-5-F Et OMe 1.4825(26.0)
1-182 i-Bu Me 3-Me-5-F Ac OMe 86.4
1-183 i-Bu Me 3-Me-5-F COPh OMe 124.1-130.8
1-184 i-Bu Me 3-Me-5-F COOMe OMe 64.5-80.5
1-185 i-Bu Me 3-Me-5-F COO-i-Bu OMe 1.4789(23.7)
1-186 i-Bu Me 3-Me-5-F COO(CH2)2OMe OMe 1.4857 (22.3)
1-187 i-Bu Me 3-Me-5-F CH2OEt OMe 1.4804 (23.8)
1-188 i-Bu Me 3-Me-5-Cl H H 160-161
1-189 i-Bu Me 3-Me-5-Cl H OMe 144-146
1-190 i-Bu Me 3-Me-5-Cl Me OMe 1.4919(25.6)
1-191 i-Bu Me 3-Me-5-Cl Et OMe 1.4938(26.0)
1-192 i-Bu Me 3-Me-5-Cl CH2OMe OMe 1.4961(26.0)
1-193 i-Bu Me 3-Me-5-Cl CH2OEt OMe 1.4932(25.6)
1-194 i-Bu Me 3-Me-5-Cl COOMe OMe 1.4883(25.6)
1-195 i-Bu Me 3-Me-5-Cl COOEt OMe 1.4915(26.0)
1-196 i-Bu Me 3-Me-5-Cl COO-i-Bu OMe 1.4850(25.6)
1-197 i-Bu Me 3-Me-5-Cl COO(CH2)2OMe OMe 1.4946(26.0)
40

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-198 i-Bu Me 3-Me-5-Cl Ac OMe 102.6-102.8
1-199 i-Bu Me 3-Me-5-Cl COEt OMe 101.8-104.2
1-200 i-Bu Me 3-Me-5-Cl COPh OMe 1.5210(26.0)
1-201 i-Bu Et 3-Me-5-Cl H H 104.5-106
1-202 i-Bu Me 3-Me-5-I H H 152-153
1-203 i-Bu Me 3-Me-5-CF3 H OMe 88-89
1-204 i-Bu Me 3-Me-5-CF3 Ac OMe 1.4710(25.7)
1-205 i-Bu Me 3-Me-5-CF3 COOMe OMe 1.4672(25.7)
1-206 i-Bu Me 3-Me-5-CF3 CH2OEt OMe 1.4652(25.7)
1-207 i-Bu Me 3-CF3-5-Me H H 1.4869(23.4)
1-208 i-Bu Me 3-CF3-5-Me Ac H 152-152.5
1-209 i-Bu Me 3-CF3-5-Me COOMe H 148.5-150
1-210 i-Bu Me 3-CF3-5-Me CH2OEt H 1.4623(22.8)
1-211 i-Bu Me 3-CF3-5-Me H OMe 138-139
1-212 i-Bu Me 3-CF3-5-Me COOMe OMe 1.4729(20.7)
1-213 i-Bu Me 3-CF3-5-Me COOEt OMe 1.4695(20.7)
1-214 i-Bu Me 3-CF3-5-Me COOCH2CH=CH2 OMe 1.4742(24.5)
1-215 i-Bu Me 3-CF3-5-Me COO(CH2)2Me OMe 1.4685(20.7)
1-216 i-Bu Me 3-CF3-5-Me COO(CH2)3Me OMe 1.4689(24.5)
1-217 i-Bu Me 3-CF3-5-Me COO-i-Bu OMe 1.4669(22.6)
1-218 i-Bu Me 3-CF3-5-Me COOPh OMe 50-55
1-219 i-Bu Me 3-CF3-5-Me COO(CH2)2OMe OMe 1.4691(22.3)
1-220 i-Bu Me 3-CF3-5-Me COSMe OMe 1.4870(24.9)
1-221 i-Bu Me 3-CF3-5-Me COSEt OMe 1.4862(24.9)
1-222 i-Bu Me 3-CF3-5-Me CH2OMe OMe 1.4669(22.4)
1-223 i-Bu Me 3-CF3-5-Me CH2OEt OMe 108-110
1-224 i-Bu Me 3-CF3-5-Me Ac OMe 1.4720(20.6)
1-225 i-Bu Me 3-CF3-5-Me CO-c-Pr OMe 1.4735(24.8)
1-226 i-Bu Me 3-CF3-5-Me H OEt
41

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-227 i-Bu Me 3-CF3-5-Me Ac OEt
1-228 i-Bu Me 3-CF3-5-Cl H H 136-137
1-229 i-Bu Me 3-CF3-5-Cl Ac H
1-230 i-Bu Me 3-CF3-5-Cl H OMe 130-132
1-231 i-Bu Me 3-CF3-5-C1 Ac OMe
1-232 i-Bu Me 3-CF3-5-Cl H OEt
1-233 i-Bu Me 3-CF3-5-Cl Ac OEt
1-234 (CH2)4Me Me 3, 5-Me2 H H 128-130
1-235 (CH2)4Me Me 3, 5-Me2 Ac H
1-236 (CH2)4Me Me 3, 5-Me2 H OMe
1-237 (CH2)4Me Me 3, 5-Me2 Ac OMe
1-238 (CH2)4Me Me 3, 5-Me2 H OEt
1-239 (CH2)4Me Me 3, 5-Me2 Ac OEt
1-240 (CH2)4Me Me 3-CF3-5-Me H H
1-241 (CH2)4Me Me 3-CF3-5-Me Ac H
1-242 (CH2)4Me Me 3-CF3-5-Me H OMe
1-243 (CH2)4Me Me 3-CF3-5-Me Ac OMe
1-244 (CH2)4Me Me 3-CF3-5-Me H OEt
1-245 (CH2)4Me Me 3-CF3-5-Me Ac OEt
1-246 CH2CMe3 Me 3, 5-Me2 H H 174-176
1-247 CH2CMe3 Me 3, 5-Me2 Ac H
1-248 CH2CMe3 Me 3, 5-Me2 H OMe
1-249 CH2CMe3 Me 3, 5-Me2 Ac OMe
1-250 CH2CMe3 Me 3, 5-Me2 H OEt
1-251 CH2CMe3 Me 3, 5-Me2 Ac OEt
1-252 CH2CMe3 Me 3-CF3-5-Me H H
1-253 CH2CMe3 Me 3-CF3-5-Me Ac H
1-254 CH2CMe3 Me 3-CF3-5-Me H OMe
1-255 CH2CMe3 Me 3-CF3-5-Me Ac OMe
42

Table 1 (continued)

No. G Y1 Y2 R1 R2 Property
1-256 CH2CMe3 Me 3-CF3-5-Me H OEt
1-257 CH2CMe3 Me 3-CF3-5-Me Ac OEt
1-258 CH2CH(Me)Et Me 3, 5-Me2 H H 67-70
1-259 CH2CH(Me)Et Me 3, 5-Me2 Ac H
1-260 CH2CH(Me)Et Me 3, 5-Me2 H OMe 158-160
1-261 CH2CH(Me)Et Me 3, 5-Me2 Ac OMe
1-262 CH2CH(Me)Et Me 3, 5-Me2 H OEt
1-263 CH2CH(Me)Et Me 3, 5-Me2 Ac OEt
1-264 CH2CH(Me)Et Me 3-CF3-5-Me H H
1-265 CH2CH(Me)Et Me 3-CF3-5-Me Ac H
1-266 CH2CH(Me)Et Me 3-CF3-5-Me H OMe 143-144
1-267 CH2CH(Me)Et Me 3-CF3-5-Me Ac OMe
1-268 CH2CH(Me)Et Me 3-CF3-5-Me H OEt
1-269 CH2CH(Me)Et Me 3-CF3-5-Me Ac OEt
1-270 CH2CHEt2 Me 3, 5-Me2 H H 67-70
1-271 CH2CHEt2 Me 3, 5-Me2 Ac H
1-272 CH2CHEt2 Me 3, 5-Me2 H OMe
1-273 CH2CHEt2 Me 3, 5-Me2 Ac OMe
1-274 CH2CHEt2 Me 3, 5-Me2 H OEt
1-275 CH2CHEt2 Me 3, 5-Me2 Ac OEt
1-276 CH2CHEt2 Me 3-CF3-5-Me H H
1-277 CH2CHEt2 Me 3-CF3-5-Me Ac H
1-278 CH2CHEt2 Me 3-CF3-5-Me H OMe
1-279 CH2CHEt2 Me 3-CF3-5-Me Ac OMe
1-280 CH2CHEt2 Me 3-CF3-5-Me H OEt
1-281 CH2CHEt2 Me 3-CF3-5-Me Ac OEt
1-282 (CH2)2CHMe2 Me 3, 5-Me2 H H 152-153
1-283 (CH2)2CHMe2 Me 3, 5-Me2 Ac H
1-284 (CH2)2CHMe2 Me 3, 5-Me2 H OMe 166-167
43

Table 1 (continued)

No. G Y1 Y2
1 m R1 R2 Property
1-285 (CH2)2CHMe2 Me 3, 5-Me2 Ac OMe 1.4925(21.8)
1-286 (CH2)2CHMe2 Me 3, 5-Me2 H OEt
1-287 (CH2)2CHMe2 Me 3, 5-Me2 Ac OEt
1-288 (CH2)2CHMe2 Me 3-CF3-5-Me H H
1-289 (CH2)2CHMe2 Me 3-CF3-5-Me Ac H
1-290 (CH2)2CHMe2 Me 3-CF3-5-Me H OMe 138-140
1-291 (CH2)2CHMe2 Me 3-CF3-5-Me Ac OMe
1-292 (CH2)2CHMe2 Me 3-CF3-5-Me H OEt
1-293 (CH2)2CHMe2 Me 3-CF3-5-Me Ac OEt
1-294 (CH2)7Me Me 3, 5-Me2 H H 1.5052 (23.3)
1-295 (CH2)7Me Me 3, 5-Me2 Ac H
1-296 (CH2)7Me Me 3, 5-Me2 H OMe
1-297 (CH2)7Me Me 3, 5-Me2 Ac OMe
1-298 (CH2)7Me Me 3, 5-Me2 H OEt
1-299 (CH2)7Me Me 3, 5-Me2 Ac OEt
1-300 (CH2)7Me Me 3-CF3-5-Me H H
1-301 (CH2)7Me Me 3-CF3-5-Me Ac H
1-302 (CH2)7Me Me 3-CF3-5-Me H OMe
1-303 (CH2)7Me Me 3-CF3-5-Me Ac OMe
1-304 (CH2)7Me Me 3-CF3-5-Me H OEt
1-305 (CH2)7Me Me 3-CF3-5-Me Ac OEt
1-306 n-Pr Me 3-Me-5-CF3 H H 141-143
1-307 n-Pr Me 3-Me-5-CF3 H OMe 152-153
1-308 n-Pr Me 3-Me-5-CF3 Ac OMe 1.4688(25.6)
1-309 n-Pr Me 3-Me-5-CF3 Ac H 112-113
1-310 i-Bu Me 3-CF3-5-Me CH2OMe H 1.4690(25.9)
44

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-311 i-Bu Me 3-Me-5-F COOCH2CH2Cl OMe 1.4966(24.7)
1-312 i-Bu Me 3, 5-Me2 COOCH2CH2Cl OMe 1.5039(24.8)
1-313 i-Bu Me 3, 5-Me2 COCH2CMe3 OMe 1.4914(24.8)
1-314 i-Bu Me 3, 5-Me2 CO-c-Pr OMe 1.5061(24.9)
1-315 i-Bu Me 3-CF3-5-Me COEt H 171-173
1-316 i-Bu CI CH2CH2 3, 5-Me2 H OMe 170-171
1-317 i-Bu CI CH2CH2 3, 5-Me2 AC OMe 1.4955(24.8)
1-318 i-Bu Me 3, 5-Me2 CO-n-Pr OMe 1.4943(24.8)
1-319 i-Bu Me 3, 5-Me2 CO-t-Bu OMe 113-115
1-320 i-Bu Me 3, 5-Me2 CO(4-MeO-Ph) OMe 1.5198(25.3)
1-321 i-Bu Me 3, 5-Me2 CO(4-Me-Ph) OMe 1.5139(25.0)
1-322 i-Bu Me 3, 5-Me2 CO(4-Cl-Ph) OMe 51-64
1-323 n-Pr Me 3-Me-5-CF3 COEt OMe 1.4705(26.8)
1-324 i-Bu Me 3, 5-Me2 CO(3-Cl-Ph) OMe 1.5266(25.4)
1-325 i-Bu Me 3, 5-Me2 CO(3-Me-Ph) OMe 1.5182(25.5)
1-326 i-Bu Me 3, 5-Me2 CO(3-MeO-Ph) OMe 1.5165(26.5)
1-327 i-Bu Me 3, 5-Me2 CO(2-Me-Ph) OMe 88-128
1-328 i-Bu Me 3, 5-Me2 CO(2-Cl-Ph) OMe 121-122
1-329 i-Bu Me 3, 5-Me2 CO(2-MeO-Ph) OMe 57-83
1-330 i-Bu Me 3, 5-Me2 COCH=CH2 OMe 1.5088(24.5)
1-331 i-Bu Me 3, 5-Mez COCHClMe OMe amorphous
1-332 i-Bu Me 3, 5-Me2 CO(3-Me-2-Pyr) OMe 52-64
1-333 i-Bu Me 3, 5-Me2 SNEt2 OMe
1-334 i-Bu Me 3-CF3-5-Me CO-i-Pr H 161-163
1-335 Et Me 3-CF3-5-Me CO-i-Pr OMe 1.4680(26.4)
1-336 i-Bu Me 3, 5-Me2 CO-t-Pen OMe 95-96
45

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-337 i-Bu Me 3, 5-Me2 COCH2OMe OMe 1.4939(26.5)
1-338 i-Bu Me 3, 5-Me2 CO(4-CF3-Ph) OMe 54
1-339 i-Bu Me 3, 5-Me2 COCH2Ph OMe
1-340 i-Bu Me 3, 5-Me2 COCH=CMe2 OMe 1.5091(26.5)
1-341 i-Bu Me 3, 5-Me2 COCH=CHMe OMe 1.5082(26.5)
1-342 i-Bu Me 3, 5-Me2 COCH2CH2COOEt OMe 100-101
1-343 n-Pr Me 3-CF3-5-Me COOCH2CH=CH2 OMe 1.4728(27.0)
1-344 n-Pr Me 3-CF3-5-Me CO-t-Bu OMe 1.4715(26.9)
1-345 n-Pr Me 3-CF3-5-Me CO-n-Pr OMe 1.4660(26.8)
1-346 Et Me 3-CF3-5-Me COOCH2CH2OMe OMe 1.4695(26.2)
1-347 Et Me 3-CF3-5-Me CO-t-Bu OMe 1.4730(26.2)
1-348 i-Bu Me 3, 5-Me2 COCMe2CH2Cl OMe 1.5062(26.7)
1-349 i-Bu Me 3, 5-Me2 CO-c-Pen OMe 1.5019(26.8)
1-350 i-Bu CH=CH2 3, 5-Me2 H OMe 124-130
1-351 i-Bu CH=CH2 3, 5-Me2 CO-i-Pr OMe 1.5044(25.8)
1-352 i-Bu Me 3, 5-Me2 CO(2,4-Cl2-Ph) OMe 1.5220(26.1)
1-353 i-Bu Me 3, 5-Me2 CO(3,4-Cl2-Ph) OMe 53
1-354 n-Pr Me 3, 5-Me2 CO-i-Pr OMe 1.5075(25.1)
1-355 n-Pr Me 3-CF3-5-Me CO-i-Pr OMe 1.4741(25.8)
1-356 Et Me 3-CF3-5-Me COOCH2CH=CH2 OMe 1.4781 (25.9)
1-357 n-Pr Me 3, 5-Me2 CO-t-Bu OMe 1.4888(26.0)
1-358 n-Pr Me 3, 5-Me2 CO(4-Cl-Ph) OMe 41
1-359 Et Me 3, 5-Me2 n-Pen OMe 1.4897 (25.0)
1-360 Et Me 3, 5-Me2 CH2(4-F-Ph) OMe 107.9
1-361 Et Me 3, 5-Me2 CO-c-Bu OMe 1.4939(32.1)
1-362 Et Me 3, 5-Me2 CO-i-Pr OMe 100.3-103.4
1-363 Et Me 3, 5-Me2 CO-s-Bu OMe 1.5031(22.9)
46

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-364 Et Me 3, 5-Me2 CO-t-Bu OMe 108
1-365 Et Me 3, 5-Me2 COCMe2Et OMe 1.4983(20.5)
1-366 Et Me 3, 5-Me2 COCH2OMe OMe 1.4958(21.6)
1-367 Et Me 3, 5-Me2 COCHEt2 OMe 1.4991(21.8)
1-368 Et Me 3, 5-Me2 CO-c-Pen OMe 1.4977(30.5)
1-369 Et Me 3, 5-Me2 CO-c-Hex OMe 1.4934(25.2)
1-370 Et Me 3, 5-Me2 COCH2OPh OMe amorphous
1-371 Et Me 3, 5-Me2 COCH2-t-Bu OMe 1.4962(32.1)
1-372 Et Me 3, 5-Me2 CO(4-CF3-Ph) OMe 1.5023(32.2)
1-373 Et Me 3, 5-Me2 corph OMe 1.4211(32.0)
1-374 Et Me 3, 5-Me2 CH2OCH2CH2OMe OMe 1.4892(31.0)
1-375 Et Me 3, 5-Me2 CH20-i-Pr OMe 1.4855(30.2)
1-376 Et Me 3, 5-Me2 CH20-i-Bu OMe 1.4849(33.2)
1-377 Et Me 3, 5-Me2 CH20-n-Pr OMe 1.4982(23.1)
1-378 Et Me 3, 5-Me2 CH20-n-Bu OMe 1.4940(23.2)
1-379 Et Me 3, 5-Me2 C00CH2CC13 OMe 145.2-145.8
1-380 Et Me 3, 5-Me2 COO-n-Pen OMe 1.4960(20.2)
1-381 Et Me 3-CF3-5-Me COEt H 127-128
1-382 Et Me 3-CF3-5-Me CO-c-Bu OMe 1.4818(19.1)
1-383 Et Me 3-CF3-5-Me CO-s-Bu OMe 1.4701(24.4)
1-384 Et Me 3-CF3-5-Me COCHEt2 OMe 1.4724(24.3)
1-385 Et Me 3-CF3-5-Me CH20-n-Bu OMe 1.4670(23.7)
1-386 Et Me 3-CF3-5-Me CH20-i-Bu OMe 1.4659(21.8)
1-387 Et Me 3-CF3-5-Me CH20-n-Pr OMe 1.4672(21.8)
1-388 Et Me 3-Me-5-Cl H OMe 127.3-128.5
1-389 Et Me 3-Me-5-Cl CO-i-Pr OMe 134.1-135.4
47

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-390 Et Me 3-Me-5-Cl CO-c-Bu OMe 136.1-137.2
1-391 Et Me 3-Me-5-Cl CO-t-Bu OMe 108.6-110.4
1-392 Et Me 3-Me-5-Cl COO-i-Bu OMe 1.4931(32.1)
1-393 Et Me 3-Me-5-Cl CH20-i-Pr OMe 1.4884 (30.5)
1-394 Et Me 3-Me-5-Cl CH20-n-Bu OMe 1.4875(29.1)
1-395 Et Me 3-Me H OMe 183.8-185.4
1-396 Et Me 3-Me CO-i-Pr OMe 114.4-114.9
1-397 Et Me 3-Me CO-c-Pen OMe 1.4975(31.0)
1-398 Et Me 3-Me CH20-i-Pr OMe 1.4902(23.4)
1-399 Et Me 3, 5-Me2 CO-n-Pr OEt 1.4932 (23.0)
1-400 Et Me 3, 5-Me2 CO-i-Pr OEt 80-81
1-401 n-Pr Me 3, 5-Me2 COOCH2CH=CH2 OMe 1.4841 (23.7)
1-402 n-Pr Me 3, 5-Me2 COOCH2CHEt-n-Bu OMe 1.4894 (23.8)
1-403 n-Pr Me 3, 5-Me2 COCH2OMe OMe paste
1-404 n-Pr Me 3, 5-Me2 Me OMe 1.4983(22.0)
1-405 n-Pr Me 3, 5-Me2 Et OMe 1.4970(20.0)
1-406 n-Pr Me 3, 5-Me2 CH2CH=CH2 OMe 1.5019(23.2)
1-407 n-Pr Me 3, 5-Me2 (CH2)7 Me OMe 1.4880(23.5)
1-408 n-Pr Me 3-CF3-5-Me COOMe H 140-145
1-409 n-Pr Me 3-CF3-5-Me COOEt H 129-130
1-410 n-Pr Me 3-CF3-5-Me COEt H 140-145
1-411 n-Pr Me 3-CF3-5-Me CO-i-Pr H 135-137
1-412 n-Pr Me 3-CF3-5-Me CH20-n-Pr OMe 1.4673(21.8)
1-413 n-Pr Me 3-CF3-5-Me CH20-t-Bu OMe 1.4669(21.7)
1-414 i-Bu Me 3, 5-Me2 Me OMe paste
1-415 i-Bu Me 3, 5-Me2 n-Pr OMe paste
48

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-416 i-Bu Me 3/ 5-Me2 CH2CH=CH2 OMe 70-71
1-417 i-Bu Me 3/ 5-Me 2 CH2(4-N02-Ph) OMe paste
1-418 i-Bu Me 3/ 5-Me2 CH2Ph OMe 90-97
1-419 i-Bu Me 3/ 5-Me2 CH2(4-Me-Ph) OMe paste
1-420 i-Bu Me 3/ 5-Me2 CH20-n-Pr OMe 59-65
1-421 i-Bu Me 3, 5-Me2 CH20-n-Bu OMe paste
1-422 i-Bu Me 3/ 5-Me2 CH20-i-Pr OMe paste
1-423 i-Bu Me 3; 5-Me2 CH20-i-Bu OMe 80-82
1-424 i-Bu Me 3; 5-Me2 CH20-t-Bu OMe paste
1-425 i-Bu Me 3/ 5-Me2 CH20-s-Bu OMe paste
1-426 i-Bu Me 3, 5-Me2 CH2OCH2CF3 OMe paste
1-427 i-Bu Me 3 5-Me2 CH2OCH2CH=CH2 OMe paste
1-428 i-Bu Me 3 , 5-Me2 CH20(CH2)7Me OMe paste
1-429 i-Bu Me 3 , 5-Me2 CO-c-Bu OMe paste
1-430 i-Bu Me 3 , 5-Me2 CO-s-Bu OMe 106.1-107.8
1-431 i-Bu Me 3 5-Me2 COCHEt2 OMe 97.2-101.8
1-432 i-Bu Me 3 , 5-Me2 COCMe2Br OMe 93-106
1-433 i-Bu Me 3 , 5-Me2 CO-c-Hex OMe 1.5035(24.7)
1-434 i-Bu Me 3 , 5-Me2 CH2(2, 4, 6-
Cl3-Ph) OMe 64.2-66.7
1-435 i-Bu Me 3 , 5-Me2 ccT^ OMe 1.4991 (20.5)
1-436 i-Bu Me 3 , 5-Me2 COCHMeOMe OMe 1.4977(20.6)
1-437 i-Bu Me 3 , 5-Me2 COCMe2OMe OMe 1.4906(23.6)
1-438 i-Bu Me 3 , 5-Me2 COOPh OMe 135.3-136.1
1-439 i-Bu Me 3-] Vte-5-CF3 COO-i-Bu OMe 1.4733(21.2)
1-440 i-Bu Me 3-] ^e-5-CF3 CO-t-Bu OMe 1.4745(21.2)
1-441 i-Bu Me 3-] ^e-5-CF3 CO-i-Pr OMe 1.4722(32.1)
49

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-442 i-Bu Me 3-Me-5-CF3 CO-c-Pr OMe 1.4780 (32.0)
1-443 i-Bu Me 3-CF3-5-Me COEt OMe 1.4727 (24.1)
1-444 i-Bu Me 3-CF3-5-Me CO-i-Pr OMe 1.4720(24.2)
1-445 i-Bu Me 3-CF3-5-Me CH20-n-Pr OMe 1.4658 (22.7)
1-446 i-Bu Me 3-CF3-5-Me CH20-n-Bu OMe 1.4670(22.5)
1-447 i-Bu Me 3-CF3-5-Me CH20-i-Bu OMe 1.4625(21.9)
1-448 i-Bu Me 3-Me-5-F CO-t-Bu OMe amorphous
1-449 i-Bu Me 3-Me-5-Cl CO-i-Pr OMe 124-124.4
1-450 i-Bu Me 3-Me-5-Cl CO-t-Bu OMe 1.4860(31.4)
1-451 i-Bu Me 3-Me-5-Cl CO-c-Bu OMe 114-115.3
1-452 i-Bu Me 3-Me-5-Cl COCH2OMe OMe amorphous
1-453 i-Bu Me 3-Me-5-Cl CO-c-Pen OMe 136.2-137
1-454 i-Bu Me 3-Me-5-Cl CH20-n-Pr OMe 1.4887(31.6)
1-455 i-Bu Me 3-Me-5-Cl CH20-i-Bu OMe 60.7-64.7
1-456 i-Bu Me 3-Me CO-i-Pr OMe 67.3-68.2
1-457 i-Bu Me 3-Me CO-t-Bu OMe 124.1-125.5
1-458 i-Bu Me 3-Me CO-s-Bu OMe 1.4914(32.0)
1-459 i-Bu Me 3-Me CO-c-Bu OMe 83-88.6
1-460 i-Bu Me 3-Me CO-c-Pen OMe 1.4990(31.7)
1-461 i-Bu Me 3-Me COCHEt2 OMe 1.4905(28.5)
1-462 i-Bu Me 3-Me CH20-i-Pr OMe 1.4817 (31.7)
1-463 i-Bu H 3, 5-Me2 H OMe 82.8-90.5
1-464 i-Bu Et 3, 5-Me2 H OMe 162-163
1-465 i-Bu CH2CF3 3, 5-Me2 H OMe 176-177
1-466 i-Bu Me 3, 5-Me2 CO-i-Pr F 1.4860(22.7)
1-467 CH2CHMeEt Me 3, 5-Me2 COEt OMe 1.4929(20.1)
1-468 CH2CHMeEt Me 3, 5-Me2 CO-i-Pr OMe 1.4910(20.0)
50

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-469 n-Bu Me 3, 5-Me2 COEt OMe 1.4895(20.6)
1-470 n-Bu Me 3, 5-Me2 CO-i-Pr OMe 1.4835(18.9)
1-471 CH2CH-c-Pen Me 3-CF3-5-Me H H 200-201
1-472 CH2CH2CHMe2 Me 3, 5-Me2 COEt OMe 1.4960(20.5)
1-473 CH2CH2CHMe2 Me 3, 5-Me2 CO-i-Pr OMe 1.4950(21.6)
1-474 Et i-Pr 3, 5-Me2 H OEt 173-174
1-475 Et i-Pr 3, 5-Me2 Ac OEt 88-89
1-476 Et Me 3, 5-Me2 H O-n-Pr 104-105
1-477 Et Me 3, 5-Me2 CO-n-Pr O-n-Pr 1.4833(33.0)
1-478 Et Me 3, 5-Me2 CO-i-Pr O-n-Pr 1.4919(33.0)
1-479 Et Me 3, 5-Me2 CO-t-Bu O-n-Pr 1.4848(32.0)
1-480 Et Me 3, 5-Me2 CH2OEt O-n-Pr 1.4729(23.5)
1-481 Et Me 3-I-5-Me H H 134-135
1-482 Et Me 3, 5-Me2 COCHMeCOEt OEt
1-483 n-Pr Me 3, 5-Me2 CO-n-Pr OMe 1.4959(31.2)
1-484 n-Pr Me 3, 5-Me2 CO-s-Bu OMe 1.4960(32.3)
1-485 n-Pr Me 3, 5-Me2 CO-c-Pen OMe 1.4880(29.0)
1-486 n-Pr Me 3, 5-Me2 CH20-n-Pr OMe 1.4869(28.0)
1-487 n-Pr Me 3, 5-Me2 CH20-i-Pr OMe 1.4819(29.3)
1-488 n-Pr Me 3-Me-5-Cl H OMe 135.4-139.0
1-489 n-Pr Me 3-Me-5-Cl CO-i-Pr OMe 128.1-128.2
1-490 n-Pr Me 3-Me-5-Cl CO-s-Bu OMe 99.2-99.7
1-491 n-Pr Me 3-Me-5-Cl CO-c-Pr OMe 123.0-123.9
1-492 n-Pr Me 3-Me 5-C1 CO-c-Pen OMe 141.7-142.1
1-493 n-Pr Me 3-Me-5-Cl CH2OEt OMe 1.4954(20.7)
1-494 n-Pr Me 3-I-5-Me H H 183-185
1-495 n-Pr Me 3-Me H OMe 146.8-147.0
51

Table 1 (continued)

No. G Y1 Y2
1 m R1 R2 Property
1-496 n-Pr Me 3-Me CO-i-Pr OMe 61.6-62.9
1-497 n-Pr Me 3-Me CO-s-Bu OMe 1.4960(22.2)
1-498 n-Pr Me 3-Me CO-c-Pen OMe 1.4991(22.1)
1-499 n-Pr Me 3-Me CH20-n-Pr OMe 1.4864(22.8)
1-500 n-Pr Me 3-Me CH20-i-Pr OMe 1.4863(22.4)
1-501 n-Pr Me 3, 5-Me2 CO-n-Pr OEt 1.4892(22.7)
1-502 n-Pr Me 3, 5-Me2 CO-i-Pr OEt 1.4910(22.8)
1-503 n-Pr Me 3, 5-Me2 H O-n-Pr 158-159.5
1-504 n-Pr Me 3, 5-Me2 COEt O-n-Pr 1.4975(20.5)
1-505 n-Pr Me 3, 5-Me2 CO-n-Pr O-n-Pr 1.4940(20.5)
1-506 n-Pr Me 3, 5-Me2 CO-i-Pr O-n-Pr 1.4960(20.6)
1-507 i-Bu CH2CF3 3, 5-Me2 COEt OMe 137-138
1-508 i-Bu CH2CF3 3, 5-Me2 CO-i-Pr OMe
1-509 i-Bu i-Pr 3, 5-Me2 H OMe 166-167
1-510 i-Bu i-Pr 3, 5-Me2 CO-i-Pr OMe 107-108
1-511 i-Bu Me 3-Me-5-Cl H F 143.2-144.7
1-512 i-Bu Me 3-Me-5-Cl CO-i-Pr F 1.4888(23.0)
1-513 i-Bu Me 3-Cl-5-Me H OMe 153-161
1-514 i-Bu Me 3-Cl-5-Me CO-i-Pr OMe paste
1-515 i-Bu Me 3-Cl-5-Me CH20-i-Pr OMe paste
1-516 i-Bu Me 3-Cl-5-Me COOMe OMe amorphous
1-517 i-Bu Me 3-Br-5-Me H OMe 172-174
1-518 i-Bu Me 3-Br-5-Me CO-i-Pr OMe paste
1-519 i-Bu Me 3-Br-5-Me CH20-i-Pr OMe paste
1-520 i-Bu Me 3-I-5-Me H H 178-183
1-521 i-Bu Me 3-Br-5-Me COOMe OMe paste
1-522 i-Bu Me 3-I-5-Me H OMe amorphous
52

Table 1 (continued)
No. G Y1 Y2 R1 R2 Property
1-523 i-Bu Me 3-I-5-Me COOMe OMe paste
1-524 i-Bu Me 3-I-5-Me CO-i-Pr OMe paste
1-525 i-Bu Me 3-I-5-Me CH2OEt OMe 100-103
1-526 i-Bu Me 3-I-5-Me CH20-i-Pr OMe 100-102
1-527 i-Bu Me 3, 5-Me2 CH2CH=CMe2 OMe 81-83
1-528 CH=CMe2 Me 3, 5-Me2 H OMe
1-529 i-Bu Me 5-CF3 H OMe 170
1-530 i-Bu Me 5-CF3 CO-i-Pr OMe 1.4680(22.8)
1-531 i-Bu Et 3, 5-Me2 CO-i-Pr OMe 1.4913(23.0)
1-532 CH=CMe2 Me 3, 5-Me2 CO-i-Pr OMe
1-533 i-Bu Me 3, 5-Me2 CO-n-Pr OEt 1.4870(22.5)
1-534 i-Bu Me 3, 5-Me2 H O-n-Pr 138-139
1-535 i-Bu Me 3-1 H OMe 210-218
1-536 i-Bu Me 3-Br H OMe 203
1-537 i-Bu Me 3-C1 H OMe 174-182
1-538 i-Bu Me 3, 5-CI2 H OMe 132
1-539 i-Bu Me 3-1 CO-i-Pr OMe paste
1-540 i-Bu Me 3-Br CO-i-Pr OMe paste
1-541 i-Bu Me 3-C1 CO-i-Pr OMe paste
1-542 i-Bu Me 3-CF3 CO-i-Pr OMe paste
1-543 i-Bu Me 3, 5-CI2 CO-i-Pr OMe 113-114
1-544 i-Bu Me 3, 5-Me2 Me
Me F amorphous
1-545 i-Bu Me 3, 5-Me2 Mex>
OC s F amorphous
53

Table 1 (continued)
No. G Y1 Y2
1 m R1 R2 Property
1-546 i-Bu Me 3, 5-Me2 Me\^N
J>-Me
OC s OMe 150.4-151.2
1-547 i-Bu Me 3, 5-Me2 CH20Ac OMe 94-95
1-548 i-Bu Me 3, 5-Me2 CH2OC(=0)Et OMe 99
1-549 i-Bu Me 3, 5-Me2 CH20C(=0)-i-Pr OMe 112
1-550 i-Bu Me 3, 5-Me2 COSMe OMe
1-551 i-Bu Me 3, 5-Me2 COSEt OMe
54

Table 2 (Y^Me)
No. G Xn Y2
1 m R1 R2 Property
2-1 Et 6-Me 3, 5-Me2 H H
2-2 Et 6-Me 3, 5-Me2 Ac H
2-3 Et 6-Me 3, 5-Me2 H OMe
2-4 Et 6-Me 3, 5-Me2 Ac OMe
2-5 Et 6-Me 3, 5-Me2 H OEt
2-6 Et 6-Me 3, 5-Me2 Ac OEt
2-7 Et 6-Me 3-CF3-5-Me H H
2-8 Et 6-Me 3-CF3-5-Me Ac H
2-9 Et 6-Me 3-CF3-5-Me H OMe
2-10 Et 6-Me 3-CF3-5-Me Ac OMe
2-11 Et 6-Me 3-CF3-5-Me H OEt
2-12 Et 6-Me 3-CF3-5-Me Ac OEt
2-13 n-Pr 6-Me 3, 5-Me2 H H 128-131
2-14 n-Pr 6-Me 3, 5-Me2 Ac H
2-15 n-Pr 6-Me 3, 5-Me2 H OMe 132-134
2-16 n-Pr 6-Me 3, 5-Me2 Ac OMe 1.4905(25.9)
2-17 n-Pr 6-Me 3, 5-Me2 H OEt 154-155
2-18 n-Pr 6-Me 3, 5-Me2 Ac OEt
2-19 n-Pr 6-Me 3-CF3-5-Me H H
2-20 n-Pr 6-Me 3-CF3-5-Me Ac H
2-21 n-Pr 6-Me 3-CF3-5-Me H OMe 104-106
55

Table 2 (continued)

No. G Xn Y2
1 m R1 R2 Property
2-22 n-Pr 6-Me 3-CF3-5-Me Ac OMe 1.4751(26.7)
2-23 n-Pr 6-Me 3-CF3-5-Me H OEt 152-153
2-24 n-Pr 6-Me 3-CF3-5-Me Ac OEt
2-25 n-Pr 6-Me 3-Me-5-Cl H OMe 127-128.5
2-26 n-Pr 6-Me 3-CF3-5-Me COEt OMe 151-152
2-27 i-Bu 6-C1 3, 5-Me2 H OMe 106-109
2-28 i-Bu 6-C1 3, 5-Me2 Ac OMe amorphous
2-29 Et 6-Me 3, 5-Me2 CO-c-Pr OMe 138-140
2-30 Et 6-Me 3, 5-Me2 COEt OMe 132-134
2-31 Et 6-Me 3-CF3-5-Me CO-n-Pr OMe 1.4960(26.6)
2-32 n-Pr 6-Me 3-CF3-5-Me COOMe OMe 165-166
2-33 i-Bu 6-Me 3, 5-Me2 H OMe 126-127
2-34 n-Pr 6-Me 3, 5-Me2 CO-i-Pr OMe 1.4955(33.5)
2-35 n-Pr 6-Me 3, 5-Me2 CO-t-Bu OMe 128.5-130.2
2-36 n-Pr 6-Me 3, 5-Me2 COCHEt2 OMe 1.4918(32.6)
2-37 n-Pr 6-Me 3, 5-Me2 COO-i-Bu OMe 1.4870(30.1)
2-38 i-Bu 6-Me 3, 5-Me2 COEt OMe amorphous
2-39 Et 6-Me 3, 5-Me2 CO-i-Pr OMe 1.4952(32.0)
2-40 n-Pr 6-Me 3-Me H OMe amorphous
2-41 n-Pr 6-Me 3-Me CO-i-Pr OMe paste
2-42 n-Pr 6-Me 3, 5-Me2 CO-i-Pr OEt 111-112
2-43 i-Bu 6-Me 3, 5-Me2 CO-i-Pr OMe 38-42
2-44 n-Pr 6-Me 3-CF3-5-Me CO-i-Pr OMe 155
2-45 i-Bu 6-Me 3-CF3-5-Me H OMe 68-70
2-46 n-Pr 6-Me 3, 5-Me2 H OH 192-195
56

Table 3 (R1=H)
No G Xn R2 ^-NMRtCDCla/TMS, 5 value (ppm) ]
7.09(s, 1H), 6.54(s, 1H) , 3.76(bs,
3-1 n-Pr 6-Me F 2H) , 2.63(m, 2H) , 2.13 (s, 3H) , 1.58(111,
2H) , 0.96(t, 3H)
7.18(s, 1H), 6.54(s, 1H) , 4.45-
3-2 n-Pr 6-Me H 4.20(br, 2H), 4.27 (m, 1H), 2.50(dd,
2H) , 2.14(s, 3H) , 1.57(111, 2H) , 0.98(t,
3H)
7.10(s, 1H), 6.66(s, 1H), 3.72(bs,
3-3 n-Pr 6-Me OMe 2H), 3.42(s, 3H), 2.84(m, 2H), 2.14(s,
3H), 1.61(m, 2H), 1.00 (t, 3H)
7.09(s, 1H), 6.56(s, 1H), 3.78(bs,
3-4 Et 6-Me F 2H) , 2.71(m, 2H), 2.14 (s, 3H),
1.19(td, 3H)
7.10(s, 1H), 6.68(s, 1H), 3.75(bs,
3-5 Et 6-Me OMe 2H), 3.41 (s, 3H), 2.91(dd, 2H),
2.15(s, 3H), 1.22(t, 3H)
7.22(d, 1H), 6.67(d, 1H), 6.52(dd,
3-6 Et H O-n-Pr 1H), 3.80(br, 2H), 3.46(t, 2H),
2.92(dd, 2H) , 1.69(dd, 2H) , 1.21(t,
3H), 0.94(t, 3H)
7.22(d, 1H), 6.66(d, 1H), 6.51(dd,
3-7 n-Pr H O-n-Pr 1H), 3.78(br, 2H), 3.47 (t, 2H),
2.85(m, 2H), 1.70(dd, 2H) , 1.60(m,
2H), 1.00 (t, 3H), 0.94(t, 3H)
7.24(d, 1H), 6.70(d, 1H), 6.53(dd,
3-8 i-Bu H O-n-Pr 1H), 3.79(bs, 2H), 3.47(t, 2H),
2.81(d, 2H), 2.10(m, 1H) , 1.70(m, 2H),
0.95(t, 3H), 0.91(d, 6H)
57

Table 4
No Y1 Y2m melting point (°C)
4-1 Me 3-Me-5-CF3 124-125.5
58

Table 5
No. ^-NMRtCDCWTMS, 5 value (ppm) ]
7.61(d, 2H) , 7.52(d, 1H), 7.17(m, 4H), 7.11(m, 1H),
1-106 3.69(s, 3H) , 3.47(s, 3H), 2.86(d, 2H), 2.39(s, 3H),
2.37(s, 3H), 1.96(m, 1H), 0.73(d, 6H)
8.27(d, 2H), 7.83(d, 2H), 7.59(d, 1H), 7.22(d, 1H),
1-107 7.17(m, 1H), 6.97(s, 1H), 3.66(s, 3H), 3.51(s, 3H),
2.91(d, 2H) , 2.36(s, 3H), 1.97 (in, 1H) , 0.77 (d, 6H)
8.04(s, 1H), 7.73(br r 1H) , 7.72(d, 1H), 7.50(d, 1H),
1-116 7.43(dc i, 1H) , 4.01(s r 3H) , 3.47(s, 3H), 2.93(d, 2H),
2.21(m, 1H), 0.94(d, 6H)
7.80 (dc i, 2H) , 7.49(d r 1H) , 7.13(dd, 2H), 7.02(dd, 1H),
1-124 6.89(d, 1H), 4.40-4.. 31 (m, 1H), 3.57(s, 3H), 2.42(d, 2H),
2.28(s, 3H) , 2.22(s, 3H) , 1.70-1.59(m, 1H), 0.78(d, 6H)
7.41(d, 1H), 7.01(dd r 1H) , 6.96(d, 1H), 3.98(dd, 2H),
1-156 3.56 (s, 3H), 3.44(s, 3H) , 2.79(d, 2H), 2.06(s, 3H),
2.00(s, 3H) , 1.86(m, 1H), 1.25(dd, 3H), 0.74(d, 6H)
7.47(d, 1H) , 7.16-7. D5(m, 2H), 3.67(s, 3H) , 3.60(dd,
1-160 2H), 3 04 (m, 1H) , 2. 38 (d, 2H) , 2.37(s, 3H) , 2.25(s, 3H) ,
1.97(111, 1H), 1.31(t, 3H) , 1.26(d, 6H), 0.77(d, 6H)
7.48(d, 1H), 7.10(d, 1H), 7.08(s, 1H), 5.11(q, 1H),
1-331 3.64 (s,
2.31(s; 3H)
3H) 3.45(s,
2.24(s, 3H) ,
3H) , 2.96(dd, 1H), 2.74(dd, 1H),
1.92(m, 1H), 1.77(d, 3H),
0.84(d, 3H) 0.65(d, 3H)
7.41(d, 1H) 7.28(m, 2H) , 7.08(d, 1H), 6.98(m, 2H),
1-370 6.84(m, 2H) 4.98(s, 2H) , 3.63(s, 3H), 3.40(s, 3H),
2.96(q# 2H) 2.18(s, 3H) , 2.14(s, 3H), 1.26(t, 3H)
7.43(d, 1H) r 7.14(d, 1H), 7.18(m, 1H) , 4.32(s, 2H) ,
1-403 3.66(s, 3H) , 3.43(s, 3H) , 3.39(s, 3H) , 2.92(m, 2H) ,
2.31 (s, 3H) , 2.23(s, 3H) , 1.51(m, 2H), 0.94(t, 3H)
7.41(d, 1H) , 7.01(m, 2H) , 3.58(s, 3H), 3.48(s, 3H),
1-414 3.44(s, 3H) , 2.79(d, 2H) , 2.06(s, 3H), 2.00(s, 3H),
1.85(111, 1H) , 0.76{d, 6H)
7.39(d 1H) , 7.00(dd / 1H) , 6.97(d, 1H), 3.88 (m, 2H),
1-415 3. 56 (s
2.00(s
0.75(d r 3H)
r 3H)
6H) , 3.44(s,
, 1.84 (m, 3H),
1H), 2.78(d, 2H), 2.05(s, 3H),
1.66(m, 2H), 0.95(t, 3H),
8.18(d , 2H) , 7.50(d, 2H), 7.38(d, 1H), 6.95(dd, 1H) ,
1-417 6.88(d
2.73(d r 1H)
, 2H) , 5.22(s,
, 2.08(s, 2H),
3H), 3.58(s, 3H), 3.41(s, 3H),
1.99(s, 3H), 1.73(m, 1H),
0.70(d r 6H)
7.33(d r 1H) , 7.23(d, 2H), 6.93(dd, 1H), 6.89(d, 1H) ,
1-419 6.83(d
3.40(s , 2H)
, 3H) , 5.06(s,
, 2.73(d, 2H),
2H), 3.79(s, 3H), 3.56(s, 3H),
2.05(s, 3H), 2.01(s, 3H),
1.74 (m , 1H) , 0.70(d, 6H)
59

Table 5 (continued)

No. ^-NMRCCDCla/TMS, 6 value ppm) ]
7.40(d, 1H), 7.16(m, 2H), 5.30(s, 2H), 3.61(t, 2H),
1-421 3.59(s,
2.04(s, 3H) ,
3H) , 3.43(s,
1.87(m, 3H) ,
1H), 2.80(d, 2H),
1.59(m, 2H), 2.09(s,
1.37(m, 3H),
2H),
0.91(t, 3H) , 0.76(d, 6H)
7.39(d, 1H), 7.18(m, 2H) , 5.31(s, 2H), 3.91(m, 1H),
1-422 3.59(3, 3H) , 3.43(s, 3H) , 2.80(d, 2H), 2.08(s, 3H),
2.04(3, 3H), 1.87(m, 1H), 1.22(d, 6H), 0.77(d, 6H)
7.39(d, 1H), 7.23(m, 2H) , 5.23(s, 2H), 3.58(s, 3H),
1-424 3.43(s, 3H) , 2.80(d/ 2H) , 2.07(s, 6H), 1.89(m, 1H),
1.26(s; 9H) , 0.78(d, 6H)
7.39(d; 1H), 7.17 (m, 2H) , 5.43(d, 1H), 5.22(d, 1H),
1-425 3.68 (m,
2.08(3, 1H),
3H) , 3.59(s,
2.04(s, 3H) ,
3H) , 3.43(s, 3H),
1.87(m, 1H), 2.80(d,
1.46-1. 2H),
63(m, 2H),
1.20(d, 3H) , 0.89(t, 3H) , 0.77(dd, 6H)
7.42(d, 1H), 7.10(m, 2H) , 5.43(s, H), 4.14(q, 2H),
1-426 3.58 (s, 3H) , 3.44(s, 3H) , 2.80(d, 2H), 2.05(s, 3H),
2.01(s, 3H) , 1.85(111, 1H), 0.76(d, 6H)
7.40(d 1H) , 7.17(dd / 1H , 7.13(d, 1H) , 5.87-5 .98(m,
1-427 1H), 5
2H) , 3 .32(3,
.59(s, 2H), 5.
3H), 3. 29 (dc
44 (s 1, 1H) , 5.20 (dd, 1H) ,
3H), 2.80(d, 2H), 2. 4.16(d,
09(s, 3H),
2.04(s 3H) , 1.87(m, 1H) , 0.76(d, 6H)
7.39(d 1H), 7.15(m, 2H) , 5.30(s, 2H) , 3.60(t, 2H),
1-428 3.59(s
2.04(s 3H) ,
3H) 3.43(s,
1.88(m, 3H)
1H) , 2.80(d, 2H),
, 1.60 (m, 2H), 2.09(s,
1.27(m, 3H),
10H),
0.88(t r 3H) 0.77(d, 6H)
7.49(d , 1H) 7.12(d, 1H) , 7.08(dd, 1H) , 3.68(s , 3H),
1-429 3.46(m , 1H) , 3.46(s, 3H) , 2.88(d, 2H), 2.40(m, 2H),
2.35(s r 3H) 2.25(s, 3H) , 1.84-2.11(m, 5H), 0. 80 (d, 6H)
7.49(d , 1H) , 7.06(d/ 1H) , 6.98(m, 1H), 3.64(s, 3H),
1-448 3.47 (s , 3H) r 2.86(d, 2H) , 2.39(s, 3H), 1.95 (m, 1H),
1.38(s r 9H) , 0.76(d, 6H)
7.49(d , 1H) , 7.18(d, 1H) , 7.13(m, 1H), 4.31(s, 2H),
1-452 3.71(s r 3H) r 3.46(s, 3H) , 3.42(s, 3H), 2.88(d, 2H),
2.32 (s , 3H) , 2.03(m, 1H) , 0.79(d, 6H)
7.53 (d r 1H) r 7.27(d, 1H) , 7.16(dd, 1H) , 3.72(s , 3H),
1-514 3.48(s , 3H) f 2.92(d, 2H) , 2.88(m, 1H) , 2.43(s, 3H),
2.07 (m , 1H) , 1.21(d, 6H) , 0.84(d, 6H)
7.41 (d , 1H) , 7.21(s, 1H) , 7.19(d, 1H), 5.28(s, 2H),
1-515 3.92 (m , 1H) , 3.63(s, 3H) , 3.44(s, 3H), 2.82(d, 2H),
2.19(s r 3H) , 1.94(m, 1H) , 1.21(d, 6H), 0.79(d, 6H)
7.55(d , 1H) , 7.32(d, 1H) , 7.16(dd, 1H) , 3.79(s , 3H),
1-516 3.76(s , 3H) , 3.49(s, 3H) , 2.94(d, 2H), 2.47(s, 3H),
2.14 (m , 1H) , 0.92(d, 6H)
60

Table 5 (continued)
No. 1H-NMR[CDC13/TMS, 5 value (ppm) ]
7.53(d, 1H) , 7.28(d/ 1H), 7.18(dd, 1H), 3.74(s, 3H),
1-518 3.47(s, 3H) , 2.92 (m, 1H), 2.91(d/ 2H), 2.42(s, 3H) ,
2.07 (m, 1H), 1.23(d, 6H), 0.84(d, 6H)
7.42(d, 1H), 7.22(d, 1H), 7.21(s, 1H), 5.28(s# 2H) ,
1-519 3.94(m, 1H), 3.63(s, 3H), 3.44(s, 3H), 2.82(d, 2H) ,
2.14(s, 3H), 1.95(m, 1H), 1.21(d, 6H), 0.79(d, 6H)
7.56(d, 1H), 7.35(d, 1H), 7.19(dd, 1H) , 3.81(s, 3H),
1-521 3.76 (s, 3H), 3.50(s, 3H), 2.94(d, 2H), 2.47(s, 3H) ,
2.14(m, 1H) , 0.92(d, 6H)
8.17 (br, 1H) , 7.78(d, 1H) , 7.47-7.53(m, 2H), 3.84(s,
1-522 3H) , 3
0.95(d, 47(s,
6H) 3H) , 2 93 (d, 2H), 2.62 (s, 3H), 2.24(m, 1H) ,
7.57(d, 1H) , 7.39(d, 1H), 7.22(dd, 1H), 3.84(s, 3H) ,
1-523 3.76(s, 3H) , 3.50(s, 3H) , 2.95(d, 2H), 2.46(s, 3H) ,
2.15(m, 1H) , 0.92(d, 6H)
7.51(d, 1H), 7.27(d, 1H), 7.20(dd, 1H), 3.74(s, 3H) ,
1-524 3.46(s, 3H) , 2.99(m, 1H), 2.90(d, 2H), 2.37(s, 3H) ,
2.07(m, 1H), 1.26(d| 6H), 0.82(d, 6H)
7.55(d, 1H), 7.16(di 1H)# 7.11(dd, 1H), 6.87(s, 1H),
1-539 3.73(s, 3H) , 3.48(s, 3H), 3.31(m, 1H), 2.89(d, 2H),
2.04(m, 1H), 1.27 (d, 6H), 0.79(d, 6H)
7.55(d 1H); 7.20(d, 1H), 7.12(dd, 1H), 7.05 (s, 1H) ,
1-540 3.72(s 3H) 3.49(s, 3H), 3.22(m, 1H), 2.90(d, 2H) ,
2.05 (m 1H) 1.26(d, 6H), 0.81(d, 6H)
7.56(d 1H) 7.21 (d, 1H), 7.15(s, 1H), 7.12(dd, 1H),
1-541 3.72(s 3H) 3.49(3, 3H), 3.17(m, 1H), 2.91(d, 2H) ,
2.05(m 1H) , 1.25(d, 6H), 0.82(d, 6H)
7.57(d 1H) , 7.17(d 1H) 7.09(dd, 1H) , 7.06(s, 1H) ,
1-542 3.78(s , 3H) , 3.49(s r 3H) , 3.26(m, 1H), 2.90(d, 2H) ,
2.03 (m , 1H) , 1.24(d r 6H) , 0.78(d, 6H)
7.51 (d r 1H) , 7.16(m r 1H) , 6.97(d, 1H), 3.82(s, 3H) ,
1-544 3.65 (s r 3H) , 2.63(t r 2H) , 2.27(s, 3H), 2.24(3, 3H) ,
2.10(s r 3H) , 2.00(s r 3H) , 1.67(m, 1H), 0.81(d, 6H)
7.47 (d , 1H) , 7.34(d , 1H) , 7.11(m, 1H), 6.94(d, 1H) ,
1-545 6.86(d r 1H) , 3.67(s r 3H) , 2.60(t, 2H), 2.51(s, 3H),
2.38 (s , 3H) , 2.28(s r 3H) , 1.73(m, 1H), 0.75(d, 6H)
7.62(s , 1H) , 7.25(s , 1H) , 3.71(s, 3H), 3.50(s, 3H),
2-28 2.88(d , 2H) , 2.38(s , 3H) , 2.32(s, 3H) , 2.24(s, 3H) ,
2.02 (m , 1H) , 0.85(d , 6H)
61

Table 5 (continued)
No. ^-NMRtCDCls/TMS, 5 value (ppm) ]
2-38 7.41(s, 1H), 7.12(s, 1H), 3.12(s, 3H) , 3.48(s, 3H),
2.88(d, 2H) , 2.38(s, 3H), 2.30(s, 3H), 2.24(s, 3H) ,
2.40-2.30(m, 2H) , 2.04(m, 1H), 1.14(t, 3H), 0.85(d, 6H)
2-40 8.26(s, 1H), 7.82(s, 1H) , 7.27(br, 2H) , 3.90(s, 3H) ,
3.45(s, 3H) , 2.95(m, 2H), 2.57(s, 3H), 2.32(s, 3H) ,
1.71(m, 2H) , 1.02(t, 3H)
2-41 7.37(s, 1H), 7.10(s, 1H), 6.30(s, 1H), 3.59(s, 3H),
3.47(s, 3H) , 3.43(m, 1H) , 2.92(br, 2H) , 2.48(s, 3H) ,
2.17(s, 3H) , 1.55(br, 2H) , 1.28(d, 6H) , 0.94(t, 3H)
The agrohorticultural agent, in particular,
agrohorticultural insecticides or acaricides, containing a
substituted pyrazolecarboxanilide derivative represented by
the formula (I) or salt of the present invention as an active
ingredient, are suitable for controlling various insect pests
such as agrohorticultural insect pests, stored grain insect
pests, sanitary insect pests, nematodes, etc., which are
injurious to paddy rice, fruit trees, vegetables, other crops,
flowers and ornamental plants, etc. They have a marked
insecticidal effect, for example, on LEPIDOPTERA including
summer fruit tortrix (Adoxophes orana fasciata), smaller tea
tortrix (Adoxophyes sp.), Manchurian fruit moth (Grapholita
inopinata), oriental fruit moth (Grapholita molesta), soybean
pod borer (Leguminivora glycinivorella) , mulberry leafroller
(Olethreutes mori), tea leafroller (Caloptilia thevivora),
Caloptilia sp. (Caloptilia zachrysa), apple leafminer
(Phyllonorycter ringoniella), pear barkminer (Spulerrina
astaurota), common white (Piers rapae crucivora), tobacco
budworm (Heliothis sp.), codling moth (Laspey resia pomonella),
diamondback moth (Plutella xylostella), apple fruit moth
(Argyresthia conjugella), peach fruit moth (Carposina
niponensis), rice stem borer (Chilo suppressalis), rice
leafroller (Cnaphalocrocis medinalis), tobacco moth (Ephestia
elutella), mulberry pyralid (Glyphodes pyloalis), yellow rice
borer (Scirpophaga incertulas), rice skipper (Parnara guttata),
rice armyworm (Pseudaletia separata), pink borer (Sesamia
inferens), common cutworm (Spodoptera litura), beet armyworm
(Spodoptera exigua), etc.;
62

HEMIPTERA including aster leafhopper (Macrosteles fascifrons),
green rice leafhopper (Nephotettix cincticepts), brown rice
planthopper (Nilaparvata lugens), whitebacked rice planthopper
(Sogatella furcifera), citrus psylla (Diaphorina citri), grape
whitefly (Aleurolibus taonabae), sweetpotato whitefly (Bemisia
tabaci), greenhouse whitefly (Trialeurodes vaporariorum),
turnup aphid (Lipaphis erysimi), green peach aphid (Myzus
persicae), Indian wax scale (Ceroplastes ceriferus), cottony
citrus scale (Pulvinaria aurantii), camphor scale
(Pseudaonidia duplex), san Jose scale (Cornstockaspis
perniciosa), arrowhead scale (Unaspis yanonensis), etc.;
TYLENCHIDA including soybean beetle (Anomala rufocuprea),
Japanese beetle (Popillia japonica), tobacco beetle
(Lasioderma serricorne), powderpost beetle (Lyctus brunneus),
twenty-eight-spotted ladybird (Epilachna vigintiotopunctata),
azuki bean weevil (Callosobruchus chinensis), vegetable weevil
(Listroderes costirostris), maize weevil (Sitophilus zeamais),
boll weevil (Anthonomus grandis grandis), rice water weevil
(Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora
femoralis), rice leaf beetle (Oulema oryzae), striped flea
beetle (Phyllotreta striolata), pine shoot beetle (Tomicus
piniperda), Colorado potato beetle (Leptinotarsa decemlineata),
Mexican bean beetle (Epilachna varivestis), corn rootworm
(Diabrotica sp.), etc.;
DIPTERA including melon fly (Dacus(Zeugodacus) cucurbitae),
oriental fruit fly (Dacus(Bactrocera) dorsalis), rice
leafminer (Agnomyza oryzae), onion maggot (Delia antiqua),
seedcorn maggot (Delia platura), soybean pod gall midge
(Asphondylia sp.), etc.; TYLENCHIDA including root-lesion
nematode (Pratylenchus sp.), potato cyst nematode (Globodera
rostochiensis), root-knot nematode (Meloidogyne sp.), citrus
nematode (Tylenchulus semipenetrans), Aphelenchus sp.
(Aphelenchus avenae), chrysanthemum foliar (Aphelenchoides
ritzemabosi), etc.; and ACARINA including citrus red mite
(Panonychus citri), fruit tree red spider mite (Panonychus
ulmi), carmine spider mite (Tetranychus cinnabarinus), Kanzawa
spider mite (Tetranychus Kanzawai Kishida), two-spotted spider
mite (Tetranychus urticae Koch), pink tea rust mite (Acaphylla
theae), pink citrus rust mite (Aculops pelekassi), purple tea
63

mice (Calacarus carinatus), pear rust mite (Epitrimerus pyri),
etc.
A substituted pyrazolecarboxanilide derivative
represented by the formula (I) or salts thereof of the present
invention is used preferably as agrohorticultural insecticides
or acaricides. However, the compound exhibits excellent
control effect against various insect pests such as insect
pests for forest and wood, insect pests for livestock farming,
sanitary insect pests, etc. and can be used as pest control
agents in various wide fields. Examples of insect pests
include: Tabanidae such as Tabanus rufidens Bigot; Muscidae
such as housefly (Musca domestica uicina MACQUART);
Gasterophilidae such as horse bot fly (Gasterophilus
intestinalis); Hypodermatidae such as cattle grub (Hypoderma
bov fS
bouis L.); Phoridae such as Megaselia spiracularis; Culicidae
such as pale house mosquito (Culex pipiens pallens), Anopheles
sinensis, one-striped mosquito (Aedes albopictus), and Aedes
japonicus; Pulicidae such as cat flea (Ctenocephalides felis),
dog flea (Ctenocephalides canis), human flea (Pulex irritans);
Ixodidae such as Ixodes ovatus Neumann; Lymantriidae such as
Euproctis similes; Rhynchophoridae such as rice weevil
(Sitophilus zeamais); Vespidae such as Vespa simillima
xanthoptera Cameron; Blattellidae such as German cockroach
(Blattela germanica); Blattidae such as American cockroach
(Periplaneta americana) and Periplaneta japonica; Pthiridae
such as public-louse (Phthirus pubis); Termitidae such as
Japanese termite (Reticulitermes speratus) and house termite
(Coptotermes formosanus); and Ixodidae such as Ixodes
persulcatus; and Macronyssidae such as tropical rat mite
(Ornithonyssus bacoti).
The agrohorticultural agent, in particular,
agrohorticultural insecticides or acaricides, containing a
substituted pyrazolecarboxanilide derivative represented by
the formula (I) or salt thereof of the present invention as an
active ingredient has a marked controlling effect on the
above-exemplified insect pests, which are injurious to paddy
field crops, upland crops, fruit trees, vegetables and other
crops, flowers and ornament plants, and the like. Therefore,
the desired effect of the agrohorticultural insecticides of
64

the present invention can be exhibited by applying the agents
to paddy field, field, fruit trees, vegetables, other crops,
seeds of flowers and ornament plants, paddy field water,
stalks and leaves, or soil at a season at which the insect
pests are expected to appear, before their appearance or at
the time when their appearance is confirmed.
Plants, for which an agrohorticultural agent of the
present invention can be used, are not specifically limited
and include, for example, plants shown hereinbelow:
Cereals (e.g. rice (Oryza sativa), barley (Hordeum
vulgare), wheat (Triticum aestivum L.), rye (Secale cereale),
oat (Avena), maize (Zea mays L.), kaoliang, etc.); legume
(soybean, adzuki bean, fava bean, bean, peanut, etc.); fruit
trees and fruits (apple, citrus fruits, pear, grapes, peach,
plum, cherry, walnut, almond, banana, strawberry, etc.);
vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion,
welsh onion, green pepper, etc.); root vegetables (carrot,
potato, sweet potato, radish, lotus root, turnip, etc.); crop
for processing (cotton, flax (Linum usitatissimum), paper
mulberry (Broussonetia kasinoki SIEB), paperbush (Edgeworthia
papyrifera), rape (Brassica napus L.), beet (Beta vulgaris),
hop, sugar cane (Saccbar-a-tum of f icinarum) , sugar beet (Beta
vulgaris var. saccharifera), olive, rubber, coffee, tobacco,
tea, etc.); gourd (pumpkin, cucumber, watermelon, melon,
etc.); grass (orchard grass, sorghum, timothy, clover, alfalfa,
etc.); grass (Korean lawn grass, bent grass, etc.); crop for
spicery (lavender (Lavandula officinalis CHAIX), rosemary,
thyme, parsley, pepper, ginger, etc.); and flowers
(chrysanthemum, rose, orchid, etc.).
Recently, gene recombinant crop (herbicide resistant crop,
insect pest resistant crop incorporated with insecticidal
toxin generating gene, disease resistant crop incorporated
with disease resistance inducer producing gene, taste improved
crop, preservability improved crop, yield improved crop, etc.),
insect sex pheromone (pheromone disrupting chemicals for leaf
roller moths, cabbage armyworm, etc.), IPM (integrated pest
management) technology using natural enemy insect have been
progressed, and pesticide compositions of the present
invention can be used in combination with or by
65

systematization with such technologies.
The agrohorticultural agent of the present invention is
generally prepared into conveniently usable forms according to
an ordinary manner for formulation of agrochemicals.
That is, the substituted pyrazolecarboxanilide derivative
represented by the formula (I) or salt of the present
invention and, optionally, an adjuvant are blended with a
suitable inert carrier in a proper proportion and prepared
into a suitable formulation form such as a suspension,
emulsifiable concentrate, soluble concentrate, wettable powder,
water dispersible granule, granules, dust, tablets, pack or
the like through dissolution, dispersion, suspension, mixing,
impregnation, adsorption or sticking.
The inert carrier usable in the present invention may be
either solid or liquid. As a material usable as the solid
carrier, there can be exemplified soybean flour, cereal flour,
wood flour, bark flour, saw dust, powdered tobacco stalks,
powdered walnut shells, bran, powdered cellulose, extraction
residue of vegetables, resins such as powdered synthetic
polymers and the like, clays (e.g. kaolin, bentonite, and acid
clay), talcs (e.g. talc and pyrophyllite), silica powders or
flakes (e.g. diatomaceous earth, silica sand, mica and white
carbon [synthetic, high-dispersion silicic acid, also called
finely divided hydrated silica or hydrated silicic acid, some
of commercially available products contain calcium silicate as
the major component]), inorganic or mineral powders such as
activated carbon, powdered sulfur, pumice, calcined
diatomaceous earth, ground brick, fly ash, sand, calcium
carbonate, calcium phosphate and the like, plastic carriers
such as polyethylene, polypropylene, poly(vinylidene chloride)
and the like, chemical fertilizers (e.g. ammonium sulfate,
ammonium phosphate, ammonium nitrate, urea and ammonium
chloride), and compost. These carriers may be used alone or as
a mixture of two or more kinds thereof.
A material usable as the liquid carrier is selected from
materials that have solubility in themselves or which, even
without such solubility, are capable of dispersing an active
ingredient with the aid of an adjuvant. The following are
typical examples of the liquid carrier and can be used alone
66

or as a mixture of two or more kinds thereof: water, alcohols
(e.g. methanol, ethanol, isopropanol, butanol and ethylene
glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl
isobutyl ketone, diisobutyl ketone and cyclohexanone), ethers
(e.g. ethyl ether, dioxane, Cellosolve, dipropyl ether and
tetrahydrofuran), aliphatic hydrocarbons (e.g. kerosene and
mineral oils), aromatic hydrocarbons (e.g. benzene, toluene,
xylene, solvent naphtha and alkylnaphthalenes), halogenated
hydrocarbons (e.g. dichloroethane, chloroform, carbon
tetrachloride and chlorobenzene), esters (e.g. ethyl acetate,
diisopropyl phthalate, dibutyl phthalate and dioctyl
phthalate), amides (e.g. dimethylformamide, diethylformamide
and dimethylacetamide), nitriles (e.g. acetonitrile), and
dimethyl sulfoxide.
The following are typical examples of the adjuvant, which
are used depending upon purposes and used alone or in
combination of two or more kinds, or in some cases, need not
be used at all.
To emulsify, disperse, dissolve and/or wet a compound as
active ingredient, a surfactant is used. As the surfactant,
there can be exemplified polyoxyethylene alkyl ethers,
polyoxyethylene alkylaryl ethers, polyoxyethylene higher fatty
acid esters, polyoxyethylene resonates, polyoxyethylene
sorbitan monolaurate, polyoxyethylene sorbitan monooleate,
alkylarylsulfonates, naphthalene sulfonic acid condensation
products, ligninsulfonates and higher alcohol sulfate esters.
Further, to stabilize the dispersion of a compound as
active ingredient, tackify it and/or bind it, the adjuvants
exemplified below may also be used, namely, there may also be
used adjuvants such as casein, gelatin, starch, methyl
cellulose, carboxymethyl cellulose, gum arabic, poly(vinyl
alcohol)s, turpentine, bran oil, bentonite and
ligninsulfonates.
To improve the flowability of a solid product, the
following adjuvants may also be used, namely, there may be
used adjuvants such as waxes, stearates, alkyl phosphates, etc.
Adjuvants such as naphthalenesulfonic acid condensation
products and polycondensates of phosphates may be used as a
peptizer for dispersible products
67

Adjuvants such as silicone oils may also be used as a
defoaming agent.
Adjuvants such as 1,2-benzisothiazoline-3-one, p-chloro-
m-xylenol, butyl p-hydroxybenzoate may also be added as a
preservative.
Further, if necessary, functional spreading agents,
active enhancers such as metabolic decomposition inhibitor
like piperonyl butoxide, anti-freezing agents such as
propylene glycol, antioxidants such as BHT, ultraviolet
absorbers, and the other additives may also be added.
The content of the compound as active ingredient may be
varied as required, and the compound as active ingredient may
be used in a proportion properly chosen in the range of 0.01
to 90 parts by weight per 100 parts of the agrohorticultural
agents. For example, in dusts or granules, the suitable
content of the compound as active ingredient is from 0.01 to
50 % by weight. In emulsifiable concentrate or wettable
powders, it is also from 0.01 to 50 % by weight.
The agrohorticultural agent of the present invention is
used to control a variety of insect pests in the following
manner: it is applied to a crop on which the insect pests are
expected to appear, or a site where appearance or growth of
the insect pests is undesirable, as it is or after being
properly diluted with or suspended in water or the like, in an
amount effective for control of the insect pests.
The applying dosage of the agrohorticultural agent of the
present invention is varied depending upon various factors
such as a purpose, insect pests to be controlled, a growth
state of a plant, tendency of insect pests appearance, weather,
environmental conditions, a formulation form, an application
method, an application site and application time. It may be
properly chosen in the range of 0.001 g to 10 kg, preferably
0.01 g to 1 kg, (in terms of the compound as active
ingredient) per 10 ares depending upon purposes.
The agrohorticultural agent of the present invention may
be used in admixture with other agrohorticultural insecticides,
acaricides, nematocides, fungicides, biotic pesticides or the
like in order to expand both spectrum of controllable insect
pest species and the period of time when effective application
68

are possible or to reduce the dosage. Furthermore, the
agrohorticultural insecticide of the present invention may be
used in admixture with herbicides, plant growth regulators,
fertilizers or the like, depending upon application situations.
As the other agrohorticultural insecticides, acaricides
and nematocides, which are used for the above purpose, there
can be exemplified agrohorticultural insecticides, acaricides
and nematocides, such as Ethion, Trichlorfon, Metamidophos,
Acephate, Dichlorvos, Mevinphos, Monocrotophos, Malathion,
Dimethoate, Formothion, Mecarbam, Vamidothion, Thiometon,
Disulfoton, Oxydeprofos, Naled, Methylparathion, Fenitrothion,
Cyanophos, Propaphos, Fenthion, Prothiofos, Profenofos,
Isofenphos, Temephos, Phenthoate, Dimethylvinphos,
Chlorfenvinphos, Tetrachlorvinphos, Phoxim, Isoxathion,
Pyraclofos, Methidathion, Chlorpyrifos, Chlorpyrifos-methyl,
Pyridaphenthion, Diazinon, Pirimiphosmethyl, Phosalone,
Phosmet, Dioxabenzophos, Quinalphos, Terbuphos, Ethoprophos,
Cadusafos, Mesulfenfos, Spirodiclofen, Metaflumizone,
Flubendiamide, DPS (NK-0795), Phosphocarb, Fenamiphos,
Isoamidophos, Fosthiazate, Isazophos, Ethoprophos, Fenthion,
Fostietane, Dichlofenthion, Thionazin, Sulprofos,
Fensulfothion, Diamidafos, Pyrethrin, Allethrin, Prallethrin,
Resmethrin, Permethrin, Tefluthrin, Bifenthrin, Fenpropathrin,
Cypermethrin, a-Cypermethrin, Cyhalothrin, X-Cyhalothrin,
Deltamethrin, Acrinathrin, Fenvalerate, Esfenvalerate,
Cycloprothrin, Ethofenprox, Halfenprox, Silafluofen,
Flucythrinate, Fluvalinate, Methomyl, Oxamyl, Thiodicarb,
Aldicarb, Alanycarb, Cartap, Metolcarb, Xylylcarb, Propoxur,
Phenoxycarb, Fenobucarb, Ethiophencarb, Fenothiocarb,
Bifenazate, BPMC, Carbaryl, Pirimicarb, Carbofuran,
Carbosulfan, Furathiocarb, Benfuracarb, Aldoxycarb,
Diafenthiuron, Diflubenzuron, Teflubenzuron, Hexaflumuron,
Novaluron, Lufenuron, Flufenoxuron, Chlorfluazuron, Fenbutatin
oxide, Tricyclohexyltin hydroxide, Sodium oleate, Potassium
oleate, Methoprene, Hydroprene, Binapacryl, Amitraz, Dicofol,
Kersen, Chlorobenzilate, Bromopropylate, Tetradifon, Bensultap,
Benzoximate, Tebufenozide, Methoxyfenozide, Pyridalyl,
Chromafenozide, Propargite, Acequinosyl, Endosulfan,
Diofenolan, Chlorfenapyl, Fenpyroximate, Tolfenpyrad, Fipronil,
69

Tebufenpyrad, Triazamate, Etoxazole, Hexythiazox, Nicotine
sulfate, Nitenpyram, Acetamiprid, Thiacloprid, Imidacloprid,
Thiamethoxam, Clothianidin, Dinotefuran, Fluazinam,
Pyriproxyfen, Hydramethylnon, Pyrimidifen, Pyridaben,
Cyromazine, TPIC (tripropyl isocyanurate), Pymetrozin,
Clofentezin, Buprofedin, Thiocyclam, Fenazaquin,
Chinomethionate, Indoxacarb, Polynactin complexes, Milbemectin,
Abamectin, Emamectin-benzoate, Spinosad, BT (Bacillus
thuringiensis), Azadirachtin, Rotenone, Hydroxypropyl starch,
Levamisole hydrochloride, Metam-sodium, Morantel tartrate,
Dazomet, Trichlamide, Pasteuria penetrans, Monacrosporium-
phymatophaguiti, etc.
As the agrohorticultural fungicides used for the same
purpose as above, there can be exemplified agrohorticultural
fungicides such as Sulfur, Lime sulfur, Copper sulfate basic,
Iprobenfos, Edifenfos, Tolclofos-methyl, Thiram, Polycarbamate,
Zineb, Maneb, Mancozeb, Propineb, Thiophanate, Thiophanate
methyl, Benomyl, Iminoctadin acetate, Iminocutadin albecylate,
Mepronil, Flutolanil, Pencycuron, Furametpyl, Thifluzamide,
Metalaxyl, Oxadixyl, Carpropamid, Dichlofluanid, Flusulfamide,
Chlorothalonil, Kresoxim-methyl, Fenoxanil, Himexazol,
Etridiazol, Fluoroimide, Procymidone, Vinclozolin, Iprodione,
Triadimefon, Bitertanol, Triflumizole, Ipconazole, Fluconazole,
Propiconazole, Diphenoconazole, Myclobutanil, Tetraconazole,
Hexaconazole, Tebuconazole, Thiadinil, Imibenconazole,
Prochloraz, Pefurazoate, Cyproconazole, Isoprothiolane,
Fenarimol, Pyrimetanil, Mepanipyrim, Pyrifenox, Fluazinam,
Triforine, Diclomezine, Azoxystrobin, Thiadiazin, Captan,
Probenazole, Acibenzolar-S-methyl, Fthalide, Tricyclazole,
Pyroquilon, Chinomethionat, Oxolinic acid, Dithianon,
Kasugamycin, Validamycin, Polyoxin, Blasticidin, Streptomycin,
etc.
Similarly, as the herbicides, there can be exemplified
herbicides such as Glyphosate, Sulfosate, Glyfosinate,
Bialaphos, Butamifos, Esprocarb, Prosulcarb, Benthiocarb,
Pyributycarb, Asulam, Linuron, Dymron, Isouron, Bensulfuron
methyl, Cyclosulfamuron, Cinosulfuron, Pyrazosulfuron ethyl,
Azimsulfuron, Imazosulfuron, Tenylchlor, Alachlor,
Pretilachlor, Clomeprop, Etobenzanid, Mefenacet, Pendimethalin,
70

Bifenox, Acifluorfen, Lactfen, Cyhalofop-butyl, Ioxynil,
Bromobutide, Alloxydim, Setoxydim, Napropamide, Indanofan,
Pyrazolate, Benzofenap, Pyraflufen-ethyl, Imazapyl,
Sulfentrazone, Cafenstrole, Bentoxazon, Oxadiazon, Paraquat,
Diquat, Pyriminobac, Simazine, Atrazine, Dimethametryn,
Triazyflam, Benflesate, Flutiacet-methyl, Quizalofop-ethyl,
Bentazon, Calcium peroxide, etc.
As to the biotic pesticides, the same effect as above can
be expected by using the agrohorticultural agent of the
present invention in admixture with, for example, viral
formulations obtained from nuclear polyhedrosis virus (NPV),
granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV),
entomopox virus (EPV), etc.; microbial pesticides utilized as
insecticides or nematicides, such as Monacrosporium
phymatophagum, Steinernema carpocapsae, Steinernema kushidai,
Pasteuria penetrans, etc.; microbial pesticides utilized as
fungicides, such as Trichoderma lignorum, Agrobacterium
radiobactor, nonpathogenic Erwinia carotovora, Bacillus
subtilis, etc.; and biotic pesticides utilized as herbicides,
such as Xanthomonas campestris, etc.
In addition, the agrohorticultural agent of the present
invention can be used in combination with biotic pesticides
including natural enemies such as Parasitic wasp (Encarsia
formosa), Parasitic wasp (Aphidius colemani), Gall-mildge
(Aphidoletes aphidimyza), Parasitic wasp (Diglyphus isaea),
Parasitic mite (Dacnusa sibirica), Predatory mite
(Phytoseiulus persimilis), Predatory mite (Amblyseius
cucumeris), Predatory bug (Orius sauteri), etc.; microbial
pesticides such as Beauveria brongniartii, etc.; and
pheromones such as (Z)-10-tetradecenyl acetate, (E,Z)-4,10-
tetradecadienyl acetate, (Z)-8-dodecenyl acetate, (Z)-ll-
tetradecenyl acetate, (Z)-13-icosen-10-one, -f&}—8-dodoconyl
acetate,—(Z)-ll-tetradecenyl acetate,—(Z)-13-icosen-lfl-one,
14-methyl-l-octadecene, etc.
Examples
The substituted pyrazolecarboxanilide derivatives
represented by the formula (I), and substituted aniline
derivative represented by the formula (II) and substituted
pyrazolecarboxic acid represented by the formula (IV), which
71

are intermediates therefore, of the present invention, are
explained in the following by referring to Examples, which
are not to be construed as limitative.
Example 1 Production of 1,3-dimethyl-5-
trifluoromethylpyrazole-4-carboxylic acid (compound No. 4-1)
4-Iodo-l,3-dimethyl-5-trifluoromethylpyrazole (8.7 g, 30
mmol) was dissolved in tetrahydrofuran (87 ml), and a solution
(1.6 M, 28 ml) of n-butyl lithium in hexane was slowly added
under an argon atmosphere with cooling with dryice-acetone
(not higher than -60°C) . After stirring at -70°C for 30 min,
the mixture was gradually warmed to room temperature while
blowing in carbon dioxide. The reaction mixture was poured
into water, the organic layer was removed, and the aqueous
layer was acidified with hydrochloric acid. The aqueous layer
was extracted with ethyl acetate. The organic layer was washed
with water, dried over magnesium sulfate and concentrated
under reduced pressure. The obtained crude crystals were
washed with hexane to give the desired compound (4.67 g) as
crystals,
yield 74%
Property: melting point 124 - 125.5°C
Example 2 Production of N-{3-isobutyl-4-[l-methoxy-2,2,2-
trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-
trifluorornethylpyrazole-4-carboxamide (compound No. 1-211)
1,5-Dimethyl-3-trifluoromethylpyrazole-4-carboxylic acid
(2.09 g, 10 mmol) was dissolved in thionyl chloride, and the
mixture was heated under reflux for 3 hr. The mixture was
concentrated under reduced pressure to give 1,5-dimethyl-3-
trifluoromethylpyrazole-4-carbonyl chloride. This was added to
a solution of 3-isobutyl-4-[l-methoxy-2,2,2-trifluoro-1-
(trifluoromethyl)ethyl]aniline (3.29 g, 10 mmol) and
triethylamine (3.03 g, 30 mmol) in tetrahydrofuran (30 ml),
and the mixture was heated under reflux for 2 hr. The reaction
mixture was diluted with ethyl acetate, washed with water, and
dried over magnesium sulfate. After concentration under
reduced pressure, the obtained residue was purified by silica
gel column chromatography (hexane:ethyl acetate=l:l) to give
the desired compound (3.64 g) as crystals,
yield 70%
72

Property: melting point 138-139°C
Example 3 Production of N-methoxymethyl-N-{3-isobutyl-4-ti-
me thoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5-
dimethyl-3-trifluoromethylpyrazole-4-carboxamide (compound No.
1-222)
Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in
tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-ti-
me thoxy-2, 2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-l,5-
dimethyl-3-trifluoromethylpyrazole-4-carboxamide (250 mg, 0.48
mmol) in tetrahydrofuran (5 ml) was added dropwise. After
stirring at room temperature for 30 min, a solution of
chloromethyl methyl ether (64 mg, 0.8 mmol) in tetrahydrofuran
(2 ml) was added and the mixture was stirred for 5 hr. The
reaction mixture was poured into diluted hydrochloric acid and
extracted with ethyl acetate. The organic layer was washed
with water, dried over magnesium sulfate, and concentrated
under reduced pressure, and the obtained residue was purified
by silica gel column chromatography (hexane:ethyl acetate=2:l)
to give the desired compound (238 mg).
yield: 88%
Property: nD1.4669 (22.4°C)
Example 4 Production of 2-methyl-5-n-propyl-4-[1,2,2,2-
tetrafluoro-1-(trifluoromethyl)ethyl]aniline (compound No. 3-
1)
5-n-Propyl-2-methylaniline (14.9 g, 0.1 mol) was diluted
in a mixed solvent (300 ml) of tert-butyl methyl ether-water
(1:1), and heptafluoroisopropyl iodide (29.6 g, 0.1 mol),
tetrabutylammonium hydrogen sulfate (3.4 g, 0.01 mol), sodium
hydrogen carbonate (8.4 g, 0.1 mol) and sodium dithionite (17
g, 0.1 mol) were successively added. The mixture was stirred
overnight at room temperature. The reaction mixture was
diluted in hexane, washed twice with 3N hydrochloric acid, and
washed with aqueous sodium hydrogen carbonate and saturated
brine. The organic layer was dried over magnesium sulfate, and
concentrated under reduced pressure. The residue was purified
by silica gel chromatography (hexane:ethyl acetate 5:1) to
give the desired compound (28.5 g).
yield:90%
Property: ^-NMRfCDCWTMS, 5 value (ppm) ] 7.09(s, 1H) , 6.54(s,
73

1H) , 3.76(bs, 2H) , 2.63(111, 2H) , 2.13(s, 3H) , 1.58(m, 2H) ,
0.96(t, 3H)
Example 5 Production of 4-[l-methoxy-2,2,2-trifluoro-l-
(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline (compound
No. 3-3)
2-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-l-
(trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) was dissolved
in a 28% solution (9.6 g) of sodium methoxide in methanol, and
the mixture was heated under reflux for 3 hr. After allowing
to cool, the reaction mixture was poured into ice water and
extracted with ethyl acetate. The organic layer was washed
with water, dried over magnesium sulfate and concentrated
under reduced pressure. The obtained residue was purified by
silica gel column chromatography (hexane:ethyl acetate=5:l) to
give the desired compound (1.31 g).
yield: 79%
Property: ^-NMRtCDCla/TMS, 5 value (ppm) ] 7.10 (s, 1H) , 6.66 (s,
1H), 3.72(bs, 2H) , 3.42(s, 3H) , 2.84(m, 2H) , 2.14(s, 3H) ,
1.61(m, 2H), 1.00(t, 3H)
Example 6 Production of 2-methyl-5-n-propyl-4-[2,2,2-
trifluoro-1-(trifluoromethyl)ethyl]aniline (compound No. 3-2)
2-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-1-
(trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) was dissolved
in dimethyl sulfoxide (20 ml), sodium borohydride (378 mg, 10
mmol) was added by small portions, and the mixture was stirred
at 60°C for 5 hr. Ice was added to the reaction mixture by
small portions, and then acetic acid was added dropwise. The
reaction mixture was diluted with ethyl acetate, and the
organic layer was washed 4 times with water, dried over
magnesium sulfate and concentrated under reduced pressure to
give the desired compound (1.47 g) .
yield:99%
Property: ^-NMRfCDCla/TMS, 5 value (ppm)] 7.18(s, 1H) , 6.54(s,
1H), 4.45-4.20(br, 2H), 4.27(m, 1H), 2.50(dd, 2H), 2.14(s, 3H),
1.57(m, 2H), 0.98(t, 3H)
Example 7 Production of N-{4-[l-methoxy-2,2,2-trifluoro-l-
(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-
trimethylpyrazole-4-carboxamide (compound No. 2-15)
1,3,5-Trimethylpyrazole-4-carbonyl chloride (172 mg, 1
74

mmol), 4-[l-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-
2-methyl-5-n-propylaniline (329 mg, 1 mmol) and triethylamine
(303 mg, 3 mmol) were dissolved in tetrahydrofuran (10 ml),
and the mixture was heated under reflux for 3 hr. The reaction
mixture was diluted with ethyl acetate, and washed with water.
The organic layer was dried over anhydrous magnesium sulfate
and concentrated under reduced pressure. The obtained residue
was purified by silica gel column chromatography (hexane:ethyl
acetate=l:2) to give the desired compound (3 60 mg).
yield: 77%
Property: melting point 132-134°C
Example 8 Production of N-acetyl-N-{4-[l-methoxy-2,2,2-
trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-
propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound
No. 2-16)
Sodium hydride (32 mg, 60%,0.8 mmol) was suspended in
tetrahydrofuran (10 ml), and a solution of N-{4-[1-methoxy-
2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-
propylphenyl}-l,3,5-trimethylpyrazole-4-carboxamide (250 mg,
0.53 mmol) in tetrahydrofuran (5 ml) was added dropwise. After
stirring at room temperature for 30 min, a solution of acetic
anhydride (80 mg, 0.78 mmol) in tetrahydrofuran (2 ml) was
added, and the mixture was stirred for one day. The reaction
mixture was poured into diluted hydrochloric acid, and the
mixture was extracted with ethyl acetate. The organic layer
was washed with water, dried over magnesium sulfate and
concentrated under reduced pressure, and the obtained residue
was purified by silica gel column chromatography (hexane:ethyl
acetate=l:3) to give the desired compound (139 mg).
yield: 52%
Property: nD1.4905 (25.9°C)
Example 9 Production of N-{2-methyl-5-n-propyl-4-[2,2,2-
trifluoro-l- (trifluoromethyl)ethyl]phenyl-2-methyl-5-n-
propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide (compound
No. 2-13)
In the same manner as in Example 7 except that 2-methyl-
5-n-propyl-4-[2,2,2-trifluoro-l-(trifluoromethyl)ethyl]aniline
was used instead of 4-[l-methoxy-2,2,2-trifluoro-1-
(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline, the
75

reaction is carried out for 3 hr to give the desired compound,
yield: 66%
Property: melting point 128-131°C
Example 10 Production of N-{3-isobutyl-4-[l-methoxy-2,2,2-
trifluoro-1-(trifluoromethyl)ethyl]phenyl}-l,3,5-
trimethylpyrazole-4-carboxamide (compound No. 1-155)
1,3,5-trimethylpyrazole-4-carbonyl chloride (3.93 g, 22.8
mmol), 3-isobutyl-4-[l-methoxy-2, 2, 2-trifluoro-1-
(trifluoromethyl)ethyl]aniline (5.0 g, 15.2 mmol), and
triethylamine (3.07 g, 30.4 mmol) were dissolved in
tetrahydrofuran (100 ml), and the mixture was heated under
reflux for 5 hr. The reaction mixture was diluted with ethyl
acetate, and washed with water. The organic layer was dried
over anhydrous magnesium sulfate and concentrated under
reduced pressure. The obtained crude crystals were washed with
ether to give the desired compound (5.62 g).
yield: 80%
Property: melting point 189-190°C
Example 11 Production of N-ethoxymethyl-N-{3-isobutyl-4-ti-
me thoxy-2 ,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-
l,3,5-trimethylpyrazole-4-carboxamide (compound No. 1-145)
Sodium hydride (29 mg, 60%,0.73 mmol) was suspended in
tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-ti-
me thoxy-2, 2,2-trifluoro-l- (trifluoromethyl)ethyl]phenyl}-
1,3,5-trimethylpyrazole-4-carboxamide (260 mg, 0.48 mmol) in
tetrahydrofuran (5 ml) was added dropwise. After stirring at
room temperature for 30 min, a solution of chloromethyl ethyl
ether (70 mg, 0.73 mmol) in tetrahydrofuran (2 ml) was added,
and the mixture was stirred for one day. The reaction mixture
was poured into diluted hydrochloric acid, and the mixture was
extracted with ethyl acetate. The organic layer was washed
with water, dried over magnesium sulfate and concentrated
under reduced pressure, and the obtained residue was purified
by silica gel column chromatography (hexane:ethyl acetate=l:3)
to give the desired compound (200 mg).
yield: 69%
Property: nD1.4892 (22.4°C)
Example 12 Production of N-isobutyloxycarbonyl-N-{3-isobutyl-
4-[l-methoxy-2,2,2-trifluoro-l-(trifluoromethyl)ethyl]phenyl}-
76

l,3,5-trimethylpyrazole-4-carboxainide (compound No. 1-152)
Sodium hydride(29 mg, 60%,0.73 mmol) was suspended in
tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-ti-
me thoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-
1,3,5-trimethylpyrazole-4-carboxamide (260 mg, 0.48 mmol) in
tetrahydrofuran (5 ml) was added dropwise. After stirring at
room temperature for 30 min, a solution of isobutyl
chlorocarbonate (100 mg, 0.73 mmol) in tetrahydrofuran (2 ml)
was added, and the mixture was stirred for one day. The
reaction mixture was poured into diluted hydrochloric acid and
extracted with ethyl acetate. The organic layer was washed
with water, dried over magnesium sulfate and concentrated
under reduced pressure, and the obtained residue was purified
by silica gel column chromatography (hexane:ethyl acetate=l:l)
to give the desired compound (280 mg).
yield: 91%
Property: nD1.4829 (22.3°C)
Example 13 Production of N-{3-isobutyl-4-[2,2,2-trifluoro-l-
(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-
carboxamide (compound No. 1-123)
1,3,5-Trimethylpyrazole-4-carbonyl chloride (2.09 g, 10.0
mmol), 3-isobutyl-4-[2,2,2-trifluoro-1-
(trifluoromethyl)ethyl]aniline (2.0 g, 6.69 mmol), and
triethylamine (1.35 g, 13.4 mmol) were dissolved in
tetrahydrofuran (60 ml), and the mixture was heated under
reflux for 5 hr. The reaction mixture was diluted with ethyl
acetate, and washed with water. The organic layer was dried
over anhydrous magnesium sulfate and concentrated under
reduced pressure, and the obtained residue was purified by
silica gel column chromatography (hexane:ethyl acetate=l:3) to
give the desired compound (2.41 g).
yield: 77%
Property: melting point 148-151°C
Example 14 Production of N-acetyl-N-{3-isobutyl-4-[2,2,2-
trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-
trimethylpyrazole-4-carboxamide (compound No. 1-125)
Sodium hydride (38 mg, 60%, 0.96 mmol) was suspended in
tetrahydrofuran (10 ml), and a solution of N-{3-isobutyl-4-
[2,2,2-trifluoro-l- (trifluoromethyl)ethyl]phenyl}-l,3,5-
77

trimethylpyrazole-4-carboxamide (300 mg, 0.64 mmol) in
tetrahydrofuran (5 ml) was added dropwise. After stirring at
room temperature for 30 min, a solution of acetyl chloride (75
mg, 0.96 mmol) in tetrahydrofuran (2 ml) was added, and the
mixture was stirred for one day. The reaction mixture was
poured into diluted hydrochloric acid and extracted with ethyl
acetate. The organic layer was washed with water, dried over
magnesium sulfate and concentrated under reduced pressure, and
the obtained residue was purified by silica gel column
chromatography (hexane:ethyl acetate=l:3) to give the desired
compound (90 mg).
yield: 28%
Property: nD1.5021 (22.5°C)
Reference Example Production of 1 4-iodo-l,3-dimethyl-5-
trifluoromethylpyrazole
Iodine (30 g) was dissolved in 60% sulfuric acid (fuming,
80 g) , and 1,3-dimethyl-5-trifluoromethylpyrazole (13.12 g, 80
mmol) was slowly added under ice-cooling. The mixture was
stirred at 0°C for 2 hr. The reaction mixture was poured into
ice water and extracted with ethyl acetate. The organic layer
was washed with aqueous sodium thiosulfate and saturated brine,
dried over magnesium sulfate and concentrated under reduced
pressure. The obtained crude crystals were washed with hexane
to give the desired compound (20 g) as crystals,
yield 86%
Property: ^-NMRtCDCls/TMS, 5 value (ppm) ] 3.98(s, 3H) , 2.26(s,
3H)
Typical formulation examples and test example of the
present invention are described below but they should not be
construed as limiting the scope of the invention.
As used in the examples, the terms "part" and "parts" are
by weight.
Formulation Example 1
Each compound listed in Table 1 or Table 2 10 parts
Xylene 70 parts
N-methylpyrrolidone 10 parts
Mixture of polyoxyethylene nonylphenyl 10 parts
ether and calcium alkylbenzenesulfonate
An emulsifiable concentrate was prepared by mixing
78

uniformly the above ingredients to effect dissolution.
Formulation Example 2
Each compound listed in Table 1 or Table 2 3 parts
Clay powder 82 parts
Diatomaceous earth powder 15 parts
A dust was prepared by mixing uniformly and grinding the
above ingredients.
Formulation Example 3
Each compound listed in Table 1 or Table 2 5 parts
Mixed powder of bentonite and clay 90 parts
Calcium ligninsulfonate 5 parts
Granules were prepared by mixing the above ingredients
uniformly, and kneading the resulting mixture together with a
suitable amount of water, followed by granulation and drying.
Formulation Example 4
Each compound listed in Table 1 or Table 2 20 parts
Mixture of kaolin and synthetic
high-dispersion silicic acid 75 parts
Mixture of polyoxyethylene nonylphenyl
ether and calcium alkylbenzenesulfonate 5 parts
A wettable powder was prepared by mixing uniformly and
grinding the above ingredients.
Test Example 1: Acaricidal action on two-spotted spider mite
(Tetranychus urticae)
Kidney bean leaf disk with a diameter of 2 cm was placed
on the wetted filter paper. Ten adult females of two-spotted
spider mite were inoculated on each leaf disk, and were
sprayed with 50 ml of test solution, prepared by diluting a
formulation containing each compound listed in Table 1 or
Table 2 as an active ingredient to adjust each of the
concentrations to 500 ppm, 50 ppm and 5 ppm. . Two days after
the treatment, the survived mites were counted. The corrected
mortality was calculated by the following equation and the
acaricidal activity was judged according to the criterion
shown below. The experiment was carried out with two
replicates under the condition at 25°C.
79

Corrected
mortality =
(%) Number of
survived
mites in —
untreated
group Number
of
survived
mites in
treated
group x 100

Number of
survived mites
in untreated
group
Criterion:
A Corrected mortality 100%
B Corrected mortality 99%-90%
C Corrected mortality 89%-80%
D Corrected mortality 79%-50%
As comparative compounds, compound Nos. 1-163 and 1-164
disclosed in JP-A-2003-48878 were used.

( 1-163 ) ( 1-164 )
As a result of the above-mentioned test, the compound Nos.
1-1, 1-3, 1-4, 1-6, 1-8, 1-10, 1-12, 1-13, 1-15, 1-16, 1-25 to
1-28, 1-31, 1-34 to 1-37, 1-45, 1-47 to 1-49, 1-51 to 54, 1-56,
1-57, 1-59, 1-67, 1-69 to 1-72, 1-74 to 1-76, 1-89, 1-101 to
1-114, 1-120 to 1-160, 1-176 to 1-225, 1-228, 1-234, 1-246, 1-
258, 1-260, 1-266, 1-270, 1-282, 1-285, 1-294, 1-306 to 1-325,
1-327 to 1-332, 1-335 to 1-337, 1-339 to 1-342, 1-344 to 1-358,
1-361 to 1-373, 1-375 to 1-380, 1-382 to 1-384, 1-386 to 1-389,
1-391 to 1-394, 1-396, 1-399 to 1-406, 1-412 to 416, 1-420 to
1-423, 1-425 to 1-427, 1-429 to 1-433, 1-435 to 1-439, 1-441
to 1-445, 1-448, 1-450 to 1-452, 1-454 to 1-463, 1-467 to 1-
470, 1-473, 1-477, 1-478, 1-482 to 1-487, 1-489 to 1-493, 1-
496 to 1-502, 1-510, 1-514, 1-515, 1-518, 1-519, 1-523 to 1-
527, 1-531, 1-539 to 1-541, 1-546 to 1-549, 2-13, 2-15 to 2-17,
2-21 to 2-23, 2-25, 2-34, 2-36 to 39, 2-41 to 43 and 2-45 of
80

the present invention showed A activity at any concentration
of 500 ppm, 50 ppm and 5 ppm, and the compound Nos. 1-23, 1-32,
1-78, 1-173, 1-284, 1-326, 1-334, 1-338, 1-343, 1-385, 1-397
to 1-398, 1-408, 1-410, 1-417, 1-440, 1-447, 1-449, 1-464, 1-
472, 1-475, 1-476, 1-479, 1-480, 1-504 to 1-506, 1-509, 1-521,
1-529, 1-530, 1-533, 1-542, 2-26 to 2-33, 2-40 and 2-46 showed
A activity at any concentration of 500 ppm and 50 ppm. In
contrast, the both control compounds did not show an acaricide
activity even at the concentration of 500 ppm.
Industrial Applicability
According to the present invention, agrohorticultural
agents, particularly insecticides and acaricides, having
superior properties as compared to conventional techniques can
be provided.
This application is based on patent application Nos.
234405/2005, 322531/2005 and 114937/2006 filed in Japan, the
contents of which are hereby incorporated by reference.
While this invention has been shown and described with
references to preferred embodiments thereof, it will be
understood by those skilled in the art that various changes in
form and details may be made therein without departing from
the scope of the invention encompassed by the appended claims.
All patents, patent publications and other publications
identified or referenced herein are incorporated by reference
in their entirety.
81

Claims
1. A substituted pyrazolecarboxanilide derivative represented
by the formula (I):
Y2m
T|LT (i)
CF3
wherein
R1 is la) a hydrogen atom, 2a) a Ci-C8 alkyl group, 3a) a halo
Ci-C6 alkyl group, 4a) a C1-C6 alkylcarbonyl group, 5a) a halo
Ci-C6 alkylcarbonyl group, 6a) a C2-C6 alkenylcarbonyl group,
7a) a halo C2-C6 alkenylcarbonyl group, 8a) a Ci-C6
alkylcarbonyl Ci-C6 alkyl group, 9a) a C3-C6 cycloalkyl group,
10a) a halo C3-C6 cycloalkyl group, 11a) a C3-C6 cycloalkyl Ci-C6
alkyl group, 12a) a halo C3-C6 cycloalkyl Ci-C6 alkyl group,
13a) a C2-C6 alkenyl group, 14a) a halo C2-C6 alkenyl group,
15a) a C2-C6 alkynyl group, 16a) a halo C2-C6 alkynyl group,
17a) a C1-C10 alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy
Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy Ci-C6 alkyl group,
20a) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group, 21a) a Ci-C6
alkylthio Ci-C6 alkyl group, 22a) a halo Ci-C6 alkylthio Ci-C6
alkyl group, 23a) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 24a)
a halo Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 25a) a C1-C6
alkylsulfonyl Ci-C6 alkyl group, 2 6a) a halo Ci-C6 alkylsulfonyl
Ci-C6 alkyl group, 27a) a mono Ci-C6 alkylamino Ci-C6 alkyl
group, 28a) a di C1-C6 alkylamino C1-C6 alkyl group wherein the
alkyl groups are the same or different, 29a) a phenyl Ci-C6
alkoxy C1-C6 alkyl group, 30a) a substituted phenyl C1-C6 alkoxy
Ci-C6 alkyl group having, on the ring, one or more, the same or
different substituents selected from a) a halogen atom, b) a
cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo C1-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6
alkoxy group, h) a C1-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl group, m) a halo
82

Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a
C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6
alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group,
34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6
alkylthiocarbonyl group, 3 6a) a mono Ci-C6 alkylaminocarbonyl
group, 37a) a di Ci-Ce alkylaminocarbonyl group wherein the
alkyl groups are the same or different, 38a) a C1-C6
alkoxycarbonyl Ci-C6 alkyl group, 39a) a Ci-C6 alkylsulfonyl
group, 40a) a halo C1-C6 alkylsulfonyl group, 41a) a cyano C1-C6
alkyl group, 42a) a phenyl Ci-C6 alkyl group, 43a) a
substituted phenyl Ci-C6 alkyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a
substituted phenylcarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-Cs alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a)
a substituted heterocyclylcarbonyl group having, on the ring,
one or more, the same or different substituents selected from
a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-
Ca alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
83

i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a
substituted phenoxycarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulf inyl group,
k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 50a) a phenoxy Ci-C6 alkylcarbonyl group,
51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on
the ring, one or more, the same or different substituents
selected from a) a halogen atom, b) a cyano group, c) a nitro
group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a
Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6
alkylthio group, i) a halo Ci-Ce alkylthio group, j) a Ci-C6
alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a
Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group,
n) a mono Ci-C6 alkylamino group, o) a di C1-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
C1-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a
substituted phenylsulfonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulf inyl group,
k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group, 54a) a di Ci-C6 alkylphosphono group
84

wherein the alkyl groups are the same or different, 55a) a di
Ci-C6 alkylphosphonothio group wherein the alkyl groups are the
same or different, 56a) a W-Ci-C6 alkyl-2\J-Ci-C6
alkoxycarbonylaminothio group, 57a) a N-Ci-C6 alkyl-A/-Ci-C6
alkoxycarbonyl Ci-C6 alkylaminothio group, 58a) a di Ci-C6
alkylaminothio group wherein the alkyl groups are the same or
different, 59a) a C3-C6 cycloalkylcarbonyl group, 60a) a halo
C3-C6 cycloalkylcarbonyl group, 61a) a Ci-C6 alkyl C3-C6
cycloalkylcarbonyl group, 62a) a halo Ci-C6 alkyl C3-C6
cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl
group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano
group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6
alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy
group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio
group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a
phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted
phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-Cs
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-Cs alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 67a) a C3-C6 cycloalkyl Ci-C6
alkylcarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl
group, 69a) a halo C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group,
70a) a phenoxy Ci-C6 alkoxycarbonyl group, 71a) a substituted
phenoxy C1-C6 alkoxycarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
85

alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a C1-C6 alkylthio group,
i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulf inyl group, 1) a Ci-C6 alkylsulf onyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 72a) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl
group, 73a) a Ci-C6 alkylcarbonyl Ci-C6 alkylcarbonyl group, or
74a) a Ci-Cs alkoxycarbonyl Ci-C6 alkylcarbonyl group;
R2 is lb) a hydrogen atom, 2b) a halogen atom, 3b) a Ci-C6 alkyl
group, 4b) a halo Ci-C6 alkyl group, 5b) a cyano group, 6b) a
hydroxy group, 7b) a Ci-C6 alkoxy group, 8b) a halo Ci-C6 alkoxy
group, 9b) a Ci-C6 alkoxy C1-C3 alkoxy group, 10b) a halo Ci-C6
alkoxy C1-C3 alkoxy group, lib) a Ci-C6 alkylthio C1-C3 alkoxy
group, 12b) a halo Ci-C6 alkylthio C1-C3 alkoxy group, 13b) a
Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 14b) a halo Ci-C6
alkylsulfinyl C1-C3 alkoxy group, 15b) a Ci-C6 alkylsulfonyl Ci~
C3 alkoxy group, 16b) a halo Ci-C6 alkylsulfonyl C1-C3 alkoxy
group, 17b) a mono Ci-C6 alkylamino C1-C3 alkoxy group, 18b) a
di C1-C6 alkylamino C1-C3 alkoxy group wherein the alkyl groups
are the same or different, 19b) a Ci-C6 alkylthio group, 20b) a
halo Ci-C6 alkylthio group, 21b) a Ci-C6 alkylsulfinyl group,
22b) a halo Ci-C6 alkylsulfinyl group, 23b) a Ci-C6
alkylsulfonyl group, 24b) a halo Ci-C6 alkylsulfonyl group,
25b) an amino group, 2 6b) a mono Ci-C6 alkylamino group, 27b) a
di C1-C6 alkylamino group wherein the alkyl groups are the same
or different, 28b) a phenoxy group, 29b) a substituted phenoxy
group having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 30b) a
phenylthio group, 31b) a substituted phenylthio group having,
86

on the ring, one or more, the same or different substituents
selected from a) a halogen atom, b) a cyano group, c) a nitro
group, d) a C1-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a
Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6
alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6
alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a
Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl group,
n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group, 32b) a phenylsulfinyl group, 33b) a
substituted phenylsulfinyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group, 34b) a phenylsulfonyl group, 35b) a
substituted phenylsulfonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 36b) a phenyl C1-C6 alkoxy group, or 37b)
a substituted phenyl C1-C6 alkoxy group having, on the ring,
one or more, the same or different substituents selected from
a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-
C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
87

group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group;
G is 1c) a C2-Cio alkyl group, 2c) a halo C2-Ci0 alkyl group, 3c)
a C3-C10 alkenyl group, 4c) a halo C3-C10 alkenyl group, 5c) a
C3-C10 alkynyl group, 6c) a halo C3-C10 alkynyl group, 7c) a C3-
C10 cycloalkyl group, 8c) a substituted C3-C10 cycloalkyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a Ci-C6 alkyl
group, and c) a halo Ci-C6 alkyl group, 9c) a C3-C10
cycloalkenyl group, 10c) a substituted C3-C10 cycloalkenyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a Ci-C6 alkyl
group, and c) a halo Ci-C6 alkyl group, lie) a C3-C8 cycloalkyl
Ci-C6 alkyl group, or 12c) a halo C3-C8 cycloalkyl C1-C6 alkyl
group;
Z is an oxygen atom or a sulfur atom;
X may be the same or different and is Id) a hydrogen atom, 2d)
a halogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a Ci~
C6 alkyl group, or 6d) a halo Ci-C6 alkyl group;
Y1 is le) a hydrogen atom, 2e) a Ci-C6 alkyl group, 3e) a halo
Ci-C6 alkyl group, 4e) a C2-C6 alkenyl group, 5e) a halo C2-Ce
alkenyl group, 6e) a C2-C6 alkynyl group, 7e) a halo C2-C6
alkynyl group, 8e) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group,
9e) a hydroxy Ci-C6 alkyl group, lOe) a Ci-C6 alkylcarbonyloxy
Ci-C6 alkyl group, lie) a C3-C6 cycloalkyl group, 12e) a halo
C3-C6 cycloalkyl group, 13e) a C3-C6 cycloalkyl Ci-C6 alkyl group,
14e) a halo C3-C6 cycloalkyl Ci-C6 alkyl group, 15e) a Ci-C6
alkylsulfonyl group, 16e) a halo Ci-C6 alkylsulfonyl group,
17e) a Ci-C6 alkylthio Ci-C6 alkyl group, 18e) a halo C1-C6
alkylthio Ci-C6 alkyl group, 19e) a Ci-C6 alkylsulfinyl Ci-C6
alkyl group, 20e) a halo Ci-C6 alkylsulf inyl Ci-C6 alkyl group,
21e) a Ci-C6 alkylsulfonyl Ci-C6 alkyl group, 22e) a halo Ci-C6
alkylsulfonyl Ci-C6 alkyl group, 23e) a mono Ci-C6 alkylamino
Ci-C6 alkyl group, 24e) a di Ci-C6 alkylamino Ci-C6 alkyl group
wherein the alkyl groups are the same or different, 25e) a
phenyl group, .2 6e) a substituted phenyl group having, on the
ring, one or more, the same or different substituents selected
88

from a) a halogen atom, b) a cyano group, c) a nitro group, d)
a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a C1-C6
alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio
group, i) a halo C1-C6 alkylthio group, j) a C1-C6 alkylsulfinyl
group, k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6
alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group, n) a
mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group;
Y2 may be the same or different and is If) a hydrogen atom, 2f)
a halogen atom, 3f) a cyano group, 4f) a nitro group, 5f) a
hydroxyl group, 6f) a mercapto group, If) an amino group, 8f)
a carboxyl group, 9f) a Ci-C6 alkyl group, lOf) a halo Ci-C6
alkyl group, llf) a C2-C6 alkenyl group, 12f) a halo C2-C6
alkenyl group, 13f) a C2-C6 alkynyl group, 14f) a halo C2-C6
alkynyl group, 15f) a tri Ci-C6 alkylsilyl C2-C6 alkynyl group
wherein the alkyl groups are the same or different, 16f) a
phenyl C2-C6 alkynyl group, 17f) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-
C6 alkyl group, 18f) a hydroxy Ci-C6 alkyl group, 19f) a Ci-C6
alkylcarbonyloxy Ci-C6 alkyl group, 20f) a C3-C6 cycloalkyl
group, 21f) a halo C3-C6 cycloalkyl group, 22f) a C3-C6
cycloalkyl Ci-Cs alkyl group, 23f) a halo C3-C6 cycloalkyl Ci-C6
alkyl group, 24f) a Ci-C6 alkoxy group, 25f) a halo Ci-C6 alkoxy
group, 2 6f) a Ci-C6 alkoxy Ci-C6 alkoxy group, 27f) a halo Ci-C6
alkoxy Ci-C6 alkoxy group, 28f) a phenyl Ci-C6 alkoxy group,
29f) a Ci-C6 alkoxy Ci-C6 alkyl group, 30f) a halo Ci-C6 alkoxy
Ci-C6 alkyl group, 31f) a C1-C6 alkylthio group, 32f) a halo Ci-
C6 alkylthio group, 33f) a Ci-C6 alkylsulfinyl group, 34f) a
halo Ci-C6 alkylsulfinyl group, 35f) a Ci-C6 alkylsulfonyl group,
36f) a halo C1-C6 alkylsulfonyl group, 37f) a Ci-C6 alkylthio
Ci-C6 alkyl group, 38f) a halo Ci-C6 alkylthio Ci-C6 alkyl group,
39f) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 40f) a halo Ci-C6
alkylsulfinyl C1-C6 alkyl group, 41f) a C1-C6 alkylsulfonyl C1-C6
alkyl group, 42f) a halo Ci-C6 alkylsulfonyl Ci-C6 alkyl group,
43f) a mono Ci-C6 alkylamino group, 44f) a di C1-C6 alkylamino
group wherein the alkyl groups are the same or different, 45f)
a phenylamino group, 4 6f) a mono Ci-C6 alkylamino Ci-C6 alkyl
group, 47f) a di Ci-C6 alkylamino Ci-C5 alkyl group wherein the
alkyl groups are the same or different, 48f) a phenyl group,
89

49f) a substituted phenyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo C1-C6 alkyl group, f) a C1-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group, 50f) a phenoxy group, 51f) a substituted
phenoxy group having, on the ring, one or more, the same or
different substituents selected from a) a halogen atom, b) a
cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a
halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo C1-C6
alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Cj.-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o)
a di C1-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 52f) a
heterocyclic group, or 53f) a substituted heterocyclic group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-Ce alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group;
m is 1 or 2; and
n is an integer of 1-3,
or a salt thereof.
2. The substituted pyrazolecarboxanilide derivative of claim 1,
wherein R1 is la) a hydrogen atom, 2a) a Ci-C6 alkyl group, 3a)
a halo Ci-C6 alkyl group, 4a) a Ci-Cs alkylcarbonyl group, 5a) a
90

halo Ci-C5 alkylcarbonyl group, 6a) a C2~C6 alkenylcarbonyl
group, 13a) a C2-C6 alkenyl group, 17a) a Ci-Cio alkoxy C1-C6
alkyl group, 18a) a halo Ci-C6 alkoxy Ci-C6 alkyl group, 19a) a
C2-C6 alkenyloxy Ci-C6 alkyl group, 20a) a C1-C6 alkoxy Ci-C6
alkoxy Ci-C6 alkyl group, 29a) a phenyl Ci-C6 alkoxy Ci-C6 alkyl
group, 30a) a substituted phenyl Ci-C6 alkoxy Ci-C6 alkyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo C1-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a
C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a Ci-Ci6
alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6 alkoxycarbonyl
group, 33a) a halo Ci-C6 alkoxycarbonyl group, 34a) a C2-C6
alkenyloxycarbonyl group, 35a) a Ci-C6 alkylthiocarbonyl group,
42a) a phenyl Ci-C6 alkyl group, 43a) a substituted phenyl Ci-C6
alkyl group having, on the ring, one or more, the same or
different substituents selected from a) a halogen atom, b) a
cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6
alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
C1-C6 alkylsulfonyl group, n) a mono Ci~C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 44a) a
phenylcarbonyl group, 45a) a substituted phenylcarbonyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di C1-C6
91

alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 4 6a) a
heterocyclylcarbonyl group, 47a) a substituted
heterocyclylcarbonyl group having, on the ring, one or more,
the same or different substituents selected from a) a halogen
atom, b) a cyano group, c) a nitro group, d) a Ci-C6 alkyl
group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g)
a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo
Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo
Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a
halo Ci-C6 alkylsulfonyl group, n) a mono Ci~C6 alkylamino group,
0) a di C1-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 48a) a
phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl
group having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C5 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
C1-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 50a) a phenoxy
Ci-C6 alkylcarbonyl group, 51a) a substituted phenoxy Ci-C6
alkylcarbonyl group having, on the ring, one or more, the same
or different substituents selected from a) a halogen atom, b)
a cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6
alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 52a) a
phenylsulfonyl group, 53a) a substituted phenylsulfonyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
92

group, f) a Ci-C6 alkoxy group, g) a halo C1-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo C1-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a Ci-C6 alkylsulfonyl group, m) a halo C1-C6 alkylsulfonyl
group, n) a mono Ci-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a Ci-C6 alkoxycarbonyl group, 58a) a di C1-C6
alkylaminothio group wherein the alkyl groups are the same or
different, 59a) a C3-C6 cycloalkylcarbonyl group, 61a) a C1-C6
alkyl C3-C6 cycloalkylcarbonyl group, 63a) a phenyl Ci-C6
alkylcarbonyl group, 64a) a substituted phenyl Ci-C6
alkylcarbonyl group having, on the ring, one or more, the same
or different substituents selected from a) a halogen atom, b)
a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e) a
halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6
alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a
phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted
phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6
alkyl group, e) a halo C1-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a C1-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group,
k) a halo Ci-Ce alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 68a) a C1-C6 alkoxy C1-C6 alkylcarbonyl
group, 73a) a Ci-C6 alkylcarbonyl Ci-C6 alkylcarbonyl group, or
74a) a Ci-C6 alkoxycarbonyl Ci-C6 alkylcarbonyl group,
or a salt thereof.
3. The substituted pyrazolecarboxanilide derivative of claim 1
or claim 2, wherein R2 is lb) a hydrogen atom, 2b) a halogen
93

atom, 6b) a hydroxy group, 7b) a Ci-C6 alkoxy group, or 8b) a
halo Ci-C6 alkoxy group,
or a salt thereof.
4. The substituted pyrazolecarboxanilide derivative of any one
of claims 1 to 3, wherein G is lc) a C2-C10 alkyl group, 3c) a
C3-C10 alkenyl group, or lie) a C3-C8 cycloalkyl C1-C6 alkyl
group,
or a salt thereof.
5. The substituted pyrazolecarboxanilide derivative of any one
of claims 1 to 4, wherein X is Id) a hydrogen atom, 2d) a
halogen atom, or 5d) a Ci-C6 alkyl group,
or a salt thereof.
6. The substituted pyrazolecarboxanilide derivative of any one
of claims 1 to 5, wherein Z is an oxygen atom;
Y1 is 2e) a Ci-C6 alkyl group, 3e) a halo Ci-C6 alkyl group, or
4e) a C2-C6 alkenyl group; and
Y2 is If) a hydrogen atom, 2f) a halogen atom, 9f) a Ci-C6 alkyl
group, lOf) a halo Ci-C6 alkyl group, or 31f) a Ci-C6 alkylthio
group,
or a salt thereof.
7. The substituted pyrazolecarboxanilide derivative of claim
1, wherein R1 is la) a hydrogen atom, 4a) a Ci-C6 alkylcarbonyl
group, 5a) a halo Ci-C6 alkylcarbonyl group, 17a) a C1-C10
alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy C1-C6 alkyl
group, *6a) a Ci-Ci6 alkoxycarbonyl group, 3^a) a halo Ci-C6
alkoxycarbonyl group, or 6 group;
R2 is lb) a hydrogen atom, or 7b) a C1-C6 alkoxy group;
G is lc) a C2-Cij0alkyl group;
Z is an oxygen atom;
X is Id) a hydrogen atom;
Y1 is 2e) a Ci-C6 alkyl group; and
Y2 may be the same or different and is If) a hydrogen atom, 2f)
a halogen atom, 9f) a Ci-Cs alkyl group, or lOf) a halo C1-C6
alkyl group,
94

or a salt thereof.
8. An agrohorticultural agent comprising a substituted
pyrazolecarboxanilide derivative of any one of claims 1 to 7
or a salt thereof as an active ingredient.
9. The agrohorticultural agent of claim 8, which is an
agrohorticultural insecticide or acaricide.

10. A method of using an agrohorticultural agent, which
comprises treating a target plant or soil with an effective
amount of an agrohorticultural agent of claim 8 or 9 so as to
control noxious organisms from useful plants.
11. A substituted aniline derivative represented by the
formula (II):

wherein
R1 is la) a hydrogen atom, 2a) a Ci-C8 alkyl group, 3a) a halo
C1-C6 alkyl group, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo
Ci-C6 alkylcarbonyl group, 6a) a C2~C6 alkenylcarbonyl group,
7a) a halo C2-C6 alkenylcarbonyl group, 8a) a Ci-C6
alkylcarbonyl Ci-C6 alkyl group, 9a) a C3~C6 cycloalkyl group,
10a) a halo C3-C6 cycloalkyl group, 11a) a C3-C6 cycloalkyl Ci-C6
alkyl group, 12a) a halo C3-C6 cycloalkyl C1-C6 alkyl group,
13a) a C2_C6 alkenyl group, 14a) a halo C2-C6 alkenyl group,
15a) a C2-C6 alkynyl group, 16a) a halo C2-C6 alkynyl group,
17a) a Ci-Cio alkoxy Ci-C6 alkyl group, 18a) a halo Ci-C6 alkoxy
Ci-C6 alkyl group, 19a) a C2-C6 alkenyloxy C1-C6 alkyl group,
20a) a Ci-C6 alkoxy Ci-C6 alkoxy Ci-C6 alkyl group, 21a) a C1-C6
alkylthio C1-C6 alkyl group, 22a) a halo Ci-C6 alkylthio C1-C6
alkyl group, 23a) a Ci-C6 alkylsulfinyl Ci-C6 alkyl group, 24a)
a halo Ci-C6 alkylsulf inyl Ci-C6 alkyl group, 25a) a Ci-C6
alkylsulfonyl Ci-C5 alkyl group, 2 6a) a halo Ci-Cs alkylsulfonyl
95

Ci-C6 alkyl group, 27a) a mono C1-C6 alkylamino Ci-C6 alkyl
group, 28a) a di C1-C6 alkylamino Ci-C6 alkyl group wherein the
alkyl groups are the same or different, 29a) a phenyl Ci-C6
alkoxy C1-C6 alkyl group, 30a) a substituted phenyl Ci-C6 alkoxy
Ci-C5 alkyl group having, on the ring, one or more, the same or
different substituents selected from a) a halogen atom, b) a
cyano group, c) a nitro group, d) a Ci-C6 alkyl group, e) a
halo Ci-Ce alkyl group, f) a C1-C6 alkoxy group, g) a halo C1-C6
alkoxy group, h) a Ci-C6 alkylthio group, i) a halo C1-C6
alkylthio group, j) a Ci-C6 alkylsulfinyl group, k) a halo C1-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 31a) a
C1-C16 alkoxycarbonyl group, 32a) a Ci-C6 alkoxy Ci-C6
alkoxycarbonyl group, 33a) a halo Ci-C6 alkoxycarbonyl group,
34a) a C2-C6 alkenyloxycarbonyl group, 35a) a Ci-C6
alkylthiocarbonyl group, 36a) a mono Ci-C6 alkylaminocarbonyl
group, 37a) a di C1-C6 alkylaminocarbonyl group wherein the
alkyl groups are the same or different, 38a) a Ci-C6
alkoxycarbonyl Ci-C6 alkyl group, 39a) a Ci-C6 alkylsulfonyl
group, 40a) a halo Ci-C6 alkylsulfonyl group, 41a) a cyano C1-C6
alkyl group, 42a) a phenyl Ci-C6 alkyl group, 43a) a
substituted phenyl C1-C6 alkyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) a
substituted phenylcarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-Cs alkoxy group, h) a C1-C6 alkylthio group,
96

i) a halo Ci-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 46a) a heterocyclylcarbonyl group, 47a)
a substituted heterocyclylcarbonyl group having, on the ring,
one or more, the same or different substituents selected from
a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-
C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 48a) a phenoxycarbonyl group, 49a) a
substituted phenoxycarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 50a) a phenoxy Ci-C6 alkylcarbonyl group,
51a) a substituted phenoxy Ci-C6 alkylcarbonyl group having, on
the ring, one or more, the same or different substituents
selected from a) a halogen atom, b) a cyano group, c) a nitro
group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a
Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6
alkylthio group, i) a halo Ci-C6 alkylthio group, j) a C1-C6
alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group, 1) a
Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group,
n) a mono C1-C6 alkylamino group, o) a di Ci-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group, 52a) a phenylsulfonyl group, 53a) a
97

substituted phenylsulfonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo C1-C6 alkylthio group, j) a C1-C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a C1-C6
alkoxycarbonyl group, 54a) a di Ci-C6 alkylphosphono group
wherein the alkyl groups are the same or different, 55a) a di
C1-C6 alkylphosphonothio group wherein the alkyl groups are the
same or different, 56a) a A/-Ci-C6 alkyl-N-Ci-C6
alkoxycarbonylaminothio group, 57a) a i\7-Ci-C6 alkyl-N-Ci-C6
alkoxycarbonyl Ci-C6 alkylaminothio group, 58a) a di C1-C6
alkylaminothio group wherein the alkyl groups are the same or
different, 59a) a C3-C6 cycloalkylcarbonyl group, 60a) a halo
C3-C6 cycloalkylcarbonyl group, 61a) a Ci-C6 alkyl C3-C6
cycloalkylcarbonyl group, 62a) a halo Ci-C6 alkyl C3-C6
cycloalkylcarbonyl group, 63a) a phenyl Ci-C6 alkylcarbonyl
group, 64a) a substituted phenyl Ci-C6 alkylcarbonyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano
group, c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6
alkyl group, f) a C1-C6 alkoxy group, g) a halo C1-C6 alkoxy
group, h) a C1-C6 alkylthio group, i) a halo Ci-C6 alkylthio
group, j) a C1-C6 alkylsulfinyl group, k) a halo Ci-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
Ci-C6 alkylsulfonyl group, n) a mono Ci-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a Ci-C6 alkoxycarbonyl group, 65a) a
phenyl C3-C6 cycloalkylcarbonyl group, 66a) a substituted
phenyl C3-C6 cycloalkylcarbonyl group having, on the ring, one
or more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a C1-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a C1-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
98

k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 67a) a C3-C6 cycloalkyl Ci-C6
alkylcarbonyl group, 68a) a Ci-C6 alkoxy Ci-C6 alkylcarbonyl
group, 69a) a halo C3-C6 cycloalkyl Ci-C6 alkylcarbonyl group,
70a) a phenoxy Ci-C6 alkoxycarbonyl group, 71a) a substituted
phenoxy Ci-C6 alkoxycarbonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci~C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 72a) a Ci-C6 alkylcarbonyloxy Ci-C6 alkyl
group, 73a) a Ci-C6 alkylcarbonyl Ci-C6 alkylcarbonyl group, or
74a) a Ci-C6 alkoxycarbonyl Ci-C6 alkylcarbonyl group;
R2 is lb) a hydrogen atom, 2b) a halogen atom, 3b) a Ci-C6 alkyl
group, 4b) a halo Ci-C6 alkyl group, 5b) a cyano group, 6b) a
hydroxy group, 7b) a C1-C6 alkoxy group, 8b) a halo C1-C6 alkoxy
group, 9b) a Ci-C6 alkoxy C1-C3 alkoxy group, 10b) a halo Ci-C6
alkoxy C1-C3 alkoxy group, lib) a Ci-C6 alkylthio C1-C3 alkoxy
group, 12b) a halo Ci-C6 alkylthio C1-C3 alkoxy group, 13b) a
Ci-C6 alkylsulfinyl C1-C3 alkoxy group, 14b) a halo Ci-C6
alkylsulfinyl C1-C3 alkoxy group, 15b) a Ci-C6 alkylsulfonyl Ci-
C3 alkoxy group, 16b) a halo Ci-C6 alkylsulfonyl C1-C3 alkoxy
group, 17b) a mono Ci-C6 alkylamino C1-C3 alkoxy group, 18b) a
di Ci-C6 alkylamino C1-C3 alkoxy group wherein the alkyl groups
are the same or different, 19b) a Ci-C6 alkylthio group, 20b) a
halo Ci-C6 alkylthio group, 21b) a Ci-C6 alkylsulfinyl group,
22b) a halo Ci-C6 alkylsulfinyl group, 23b) a Ci-C6
alkylsulfonyl group, 24b) a halo Ci-C6 alkylsulfonyl group,
25b) an amino group, 2 6b) a mono C1-C6 alkylamino group, 27b) a
di Ci-C6 alkylamino group wherein the alkyl groups are the same
or different, 28b) a phenoxy group, 29b) a substituted phenoxy
99

group having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a cyano group,
c) a nitro group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl
group, f) a Ci-C6 alkoxy group, g) a halo Ci-C6 alkoxy group, h)
a Ci-C6 alkylthio group, i) a halo Ci-C6 alkylthio group, j) a
Ci-C6 alkylsulfinyl group, k) a halo Ci-C6 alkylsulfinyl group,
1) a C1-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl
group, n) a mono C1-C6 alkylamino group, o) a di Ci-C6
alkylamino group wherein the alkyl groups are the same or
different, and p) a C1-C6 alkoxycarbonyl group, 30b) a
phenylthio group, 31b) a substituted phenylthio group having,
on the ring, one or more, the same or different substituents
selected from a) a halogen atom, b) a cyano group, c) a nitro
group, d) a Ci-C6 alkyl group, e) a halo Ci-C6 alkyl group, f) a
Ci-Cs alkoxy group, g) a halo Ci-C6 alkoxy group, h) a C1-C6
alkylthio group, i) a halo Ci-C6 alkylthio group, j) a Ci-C6
alkylsulfinyl group, k) a halo C1-C6 alkylsulfinyl group, 1) a
Ci-C6 alkylsulfonyl group, m) a halo Ci-C6 alkylsulfonyl group,
n) a mono Ci-C6 alkylamino group, o) a di Ci-C6 alkylamino group
wherein the alkyl groups are the same or different, and p) a
Ci-C6 alkoxycarbonyl group, 32b) a phenylsulfinyl group, 33b) a
substituted phenylsulfinyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo C1-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo C1-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di Ci-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 34b) a phenylsulfonyl group, 35b) a
substituted phenylsulfonyl group having, on the ring, one or
more, the same or different substituents selected from a) a
halogen atom, b) a cyano group, c) a nitro group, d) a Ci-C6
alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo C1-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo C1-C6 alkylsulfinyl group, 1) a C1-C6 alkylsulfonyl
100

group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono Ci-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group, 36b) a phenyl Ci-C6 alkoxy group, or 37b)
a substituted phenyl Ci-C6 alkoxy group having, on the ring,
one or more, the same or different substituents selected from
a) a halogen atom, b) a cyano group, c) a nitro group, d) a Ci-
Ce alkyl group, e) a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy
group, g) a halo Ci-C6 alkoxy group, h) a Ci-C6 alkylthio group,
i) a halo Ci-C6 alkylthio group, j) a Ci-C6 alkylsulfinyl group,
k) a halo Ci-C6 alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl
group, m) a halo Ci-C6 alkylsulfonyl group, n) a mono C1-C6
alkylamino group, o) a di C1-C6 alkylamino group wherein the
alkyl groups are the same or different, and p) a Ci-C6
alkoxycarbonyl group;
G is lc) a C2-Cio alkyl group, 2c) a halo C2-Cio alkyl group, 3c)
a C3-C10 alkenyl group, 4c) a halo C3-C10 alkenyl group, 5c) a
C3-C10 alkynyl group, 6c) a halo C3-C10 alkynyl group, 7c) a C3-
C10 cycloalkyl group, 8c) a substituted C3-C10 cycloalkyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a Ci-C6 alkyl
group, and c) a halo Ci-C6 alkyl group, 9c) a C3-C10
cycloalkenyl group, 10c) a substituted C3-C10 cycloalkenyl group
having, on the ring, one or more, the same or different
substituents selected from a) a halogen atom, b) a Ci-C6 alkyl
group, and c) a halo Ci-C6 alkyl group, lie) a C3-C9 cycloalkyl
Ci-C6 alkyl group, or 12c) a halo C3-C8 cycloalkyl Ci-C6 alkyl
group;
X may be the same or different and is Id) a hydrogen atom, 2d)
a halogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a Ci-
Ce alkyl group, or 6d) a halo Ci-C6 alkyl group; and
n is an integer of 1-3,
or a salt thereof.
12. The substituted aniline derivative of claim 11, wherein R1
is la) a hydrogen atom, 2a) a Ci-C6 alkyl group, 3a) a halo Ci-
C6 alkyl group, 4a) a Ci-C6 alkylcarbonyl group, 5a) a halo Ci~
C6 alkylcarbonyl group, 17a) a Ci-C6 alkoxy Ci-C6 alkyl group,
31
18a) a halo C1-C6 alkoxy Ci-Cs alkyl group, 36 a) a Ci-C(6
101

33
alkoxycarbonyl group, 3£a) a halo Ci-C6 alkoxycarbonyl group,
¥i 45
4 phenylcarbonyl group having, on the ring, one or more, the
same or different substituents selected from a) a halogen atom,
b) a cyano group, c) a nitro group, d) a C1-C6 alkyl group, e)
a halo Ci-C6 alkyl group, f) a Ci-C6 alkoxy group, g) a halo Ci-
C6 alkoxy group, h) a Ci-C6 alkylthio group, i) a halo Ci-C6
alkylthio group, j) a C1-C6 alkylsulfinyl group, k) a halo C1-C6
alkylsulfinyl group, 1) a Ci-C6 alkylsulfonyl group, m) a halo
C1-C6 alkylsulfonyl group, n) a mono C1-C6 alkylamino group, o)
a di Ci-C6 alkylamino group wherein the alkyl groups are the
same or different, and p) a C1-C6 alkoxycarbonyl group;
R2 is lb) a hydrogen atom, 2b) a halogen atom, 6b) a hydroxy
group, 7b) a Ci-C6 alkoxy group, or 8b) a halo C1-C6 alkoxy
group;
G is lc) a C2-Cio alkyl group; and
X is Id) a hydrogen atom, or 5d) a Ci-C6 alkyl group,
or a salt thereof.
102
13. 1, 3-Dimethyl-5-trifluoromethylpyrazole-4-carboxylic acid
or a salt thereof.

The substituted pyrazolecarboxanilide derivatives
represented by of the formula (I)
wherein R1 is H, alkyl, alkylcarbonyl, alkenylcarbonyl,
cycloalkyl, phenylalkyl, phenylcarbonyl and the like; R2 is H,
halogen, alkyl, CN, OH, alkoxy, phenoxy, phenylthio,
phenylsulfonyl and the like; G is alkyl, alkenyl, alkynyl,
cycloalkyl, C3-C10 cycloalkenyl and the like; Z is 0 or S; X is
H, halogen, CN, NO2, alkyl and the like; Y1 is H, alkyl,
alkenyl, phenyl, alkoxyalkyl and the like; Y2 is H, halogen, CN,
NO2, OH, mercapto, amino, carboxyl, C1-C6 alkyl, phenyl, phenoxy,
heterocycle and the like, m is 1 or 2; and n is 1-3, and salts
thereof exhibit a superior effect as agrohorticultural
insecticides or acaricides.

Documents:

01030-kolnp-2008-abstract.pdf

01030-kolnp-2008-claims.pdf

01030-kolnp-2008-correspondence others.pdf

01030-kolnp-2008-description complete.pdf

01030-kolnp-2008-form 1.pdf

01030-kolnp-2008-form 2.pdf

01030-kolnp-2008-form 3.pdf

01030-kolnp-2008-form 5.pdf

01030-kolnp-2008-international publication.pdf

01030-kolnp-2008-international search report.pdf

01030-kolnp-2008-pct priority document notification.pdf

01030-kolnp-2008-pct request form.pdf

1030-KOLNP-2008-(03-04-2014)-ANNEXURE TO FORM 3.pdf

1030-KOLNP-2008-(03-04-2014)-CORRESPONDENCE.pdf

1030-KOLNP-2008-(05-11-2012)-CORRESPONDENCE.pdf

1030-KOLNP-2008-(06-01-2015)-CORRESPONDENCE.pdf

1030-KOLNP-2008-(26-09-2014)-CLAIMS.pdf

1030-KOLNP-2008-(26-09-2014)-CORRESPONDENCE.pdf

1030-KOLNP-2008-(26-09-2014)-FORM-13.pdf

1030-KOLNP-2008-(26-09-2014)-FORM-3.pdf

1030-KOLNP-2008-(26-09-2014)-FORM-5.pdf

1030-KOLNP-2008-(26-09-2014)-OTHERS 1.pdf

1030-KOLNP-2008-(26-09-2014)-OTHERS 2.pdf

1030-KOLNP-2008-(26-09-2014)-OTHERS 3.pdf

1030-KOLNP-2008-(26-09-2014)-OTHERS 4.pdf

1030-KOLNP-2008-(26-09-2014)-OTHERS 5.pdf

1030-KOLNP-2008-(26-09-2014)-OTHERS.pdf

1030-KOLNP-2008-(26-09-2014)-PETITION UNDER RULE 137.pdf

1030-KOLNP-2008-CORRESPONDENCE-1.1.pdf

1030-KOLNP-2008-CORRESPONDENCE-1.2.pdf

1030-kolnp-2008-Correspondence-240215.pdf

1030-kolnp-2008-form 18.pdf

1030-KOLNP-2008-FORM 26.pdf

1030-kolnp-2008-OTHERS-240215.pdf

1030-KOLNP-2008-OTHERS.pdf

« Previous Patent

Next Patent »

Patent Number

266059

Indian Patent Application Number

1030/KOLNP/2008

PG Journal Number

14/2015

Publication Date

03-Apr-2015

Grant Date

30-Mar-2015

Date of Filing

10-Mar-2008

Name of Patentee

NIHON NOHYAKU CO., LTD

Applicant Address

2-5, NIHONBASHI 1-CHOME, CHUO-KU, TOKYO

Inventors:

#	Inventor's Name	Inventor's Address
1	TAKASHI FURUYA	C/O NINON NOHYAKU CO., LTD. RESEARCH CENTER, 345 OYAMADA-CHO, KAWACHINAGANO-SHI, OSAKA 586-0094
2	KOZO MACHIYA	10-6, TAMAGAWAGAKUEN 7-CHOME, MACHIDA-SHI, TOKYO 194-0041 TOKYO
3	AKIYUKI SUWA	C/O NINON NOHYAKU CO., LTD. RESEARCH CENTER, 345 OYAMADA-CHO, KAWACHINAGANO-SHI, OSAKA 586-0094
4	NORIAKI YASOKAWA	C/O NINON NOHYAKU CO., LTD. RESEARCH CENTER, 345 OYAMADA-CHO, KAWACHINAGANO-SHI, OSAKA 586-0094
5	SHINSUKE FUJIOKA	C/O NINON NOHYAKU CO., LTD. RESEARCH CENTER, 345 OYAMADA-CHO, KAWACHINAGANO-SHI, OSAKA 586-0094
6	HIDEO KANNO	C/O NINON NOHYAKU CO., LTD. RESEARCH CENTER, 345 OYAMADA-CHO, KAWACHINAGANO-SHI, OSAKA 586-0094

PCT International Classification Number

C07D 231/14

PCT International Application Number

PCT/JP2006/316198

PCT International Filing date

2006-08-11

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	114937/2006	2006-04-18	Japan
2	234405/2005	2005-08-12	Japan
3	322531/2005	2005-11-07	Japan