Title of Invention

PHTHALAMIDE DERIVATIVES AND AGROHORTICULTURAL INSECTICIDE CONTAINING THE SAME

Abstract ABSTRACT T126/M AS/99 "Phthaiamide derivatives and agrohorticullural insecticide containing the same" The present invention provides a phthaiamide derivative of the formula (I): [wherein A' is (substituted) C1-C8 alkylene, (substituted) C3-C6 alkenylene, (substituted) C3-C8 alkynylene, etc, R' is H, (halo) C3-C4 cycloalkyl, (substituted) phenyl, (substi¬tuted) heterocycle, -A2-R6, etc., R2 and R1 are H, C3C6 cycloalkyl, -A2-R4, etc., A2 is -c(=0)-, -C(=S)- or -C(=NR')-, R4 is H, alkyl, (substituted) phenyl, (substi¬tuted) heterocycle, etc., X and y are halogen, cyano, nitro, (halo) C1-C6 alkyl, (halo) C1-C6 alkoxy, etc., 1 is 0-4, m is 0-5, n is 0-2]; and an agrohorticultural insecticide containing said compound as active ingredient and exhibiting an excellent insecticidal effect.
Full Text

BACKGROUND OF THE INVENTION
FIELD OF THE INVENTION
The present invention relates to a phthalamide derivative or salt thereof, an agrohorticultural insecti¬cide containing said compound as an active ingredient thereof, and a method for using the agrohorticultural agent.
RELATED ART
JP-A-61-180753 discloses some of the phthalamide derivatives of the present invention. However, in that patent application specification, there is neither disclosed nor suggested about usefulness of said deriva¬tives as an agrohorticultural insecticide. Further, although similar compounds are disclosed in JP-Ar5_9-163353. and J. c. s. Perlcin I, 1338-1350 (1978), etc., there is made no mention nor suggestion in these publications about usefulness of those compounds as an agrohorticultural insecticide.
SUMMARY OF THE INVENTION
The present inventors have conducted extensive studies with the aim of developing a novel agrohorti¬cultural agent. As a result, it has been found that the phthalamide derivatives of the present invention represented by general formula (I), which are novel

compounds not found in literature, can be put to a novel use as an agrohorticultural insecticide comprising not only these novel compounds but also some known compounds disclosed in prior art. Based on this finding, the present invention has been accomplished.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to phthalamide derivatives represented by the following general formula (I) or salt thereof, an agrohorticultural insecticide containing, as active ingredients thereof, the phthalamide derivative represented by the general formula {1} or salt thereof and some known compounds, and a method for using the same:

wherein A^ represents C^-Cg alkylene group, substituted C^-C^ alkylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo Ci-C^ alkyl group, Cj-Cg alkoxy group, halo C1-C5 alkoxy group, Cj-Cj alkylthio group, halo Cj-Cj alkylthio group, Cj-Cg alkylsulfinyl group, halo Ci-C(i alkylsulfinyl group, Ci-Cj alkylsulfonyl group, halo

Ci-Cg alkylsulfonyl group, hydroxy C^-C^ alkyl group, Ci-Cg alkoxy C^-C^ alkyl group, Cj-C^ alkylthio Ci-C^ alkyl group, Ci-Cd alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-Ce alkyl group, halo Ci-C^ alkyl group, C^-Cj alkoxy group, halo C^-Cg alkoxy group, Cj-Cj alkylthio group, halo C-^-Cs alkylthio group, Cj-Cg alkylsulfinyl group, halo C-^-Cf alkylsulfinyl group, Ci-C^ alkylsulfonyl group, halo C^-C^ alkylsulfonyl group, mono Cj-Ce alkylamino group, di Ci-C^ alkylamino group in which Cj-C^ alkyl groups may be same or different, and C^-Cs alkoxycarbonyl group, C3-C8 alkenylene group, substituted C^-Cs alkenylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo Ci-C^ alkyl group, Ci-C^ alkoxy group, halo C^-Cj alkoxy group, Ci-Cg alkylthio group, halo Ci-C^ alkylthio group, Cj-Ce alkyl¬sulfinyl group, halo C-^-C^ alkylsulfinyl group, Cj-Cg alkyl¬sulfonyl group, halo Cj-Cj alkylsulfonyl group, Ci-C^ alkylthio Cj-Cg alkyl group, Cj-Cj alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo Cj-C^ alkyl group, Cj-Ct; alkoxy group, halo Ci-C^ alkoxy group, Cj-Cj alkylthio group, halo Ci-C^ alkyl¬thio group, Ci-Cg alkylsulfinyl group, halo Ci-Cg alkyl¬sulfinyl group, Ci-C( alkylsulfonyl group, halo Cj-Cj alkyl-

sulfonyl group, mono Cj-Cj alkylamino group, di Ci-C^ alkyl-amino group in which c^-c^, alkyl groups may be same or different, and C^-C(, alkoxycarbonyl group, Cj-Cg alkynylene group, or substituted Cj-Cg alkynylene group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, halo C,-C6 alkyl group, C^-Cj alkoxy group, halo C^-C^ alkoxy group, Ci-C^ alkylthio group, halo C^-C^ alkylthio group, C^-Cfi alkylsulfinyl group, halo Ci-Cg alkylsulfinyl group, Cj-Cg alkylsulfonyl group, halo C^-Cg alkylsulfonyl group, C^-Cj alkylthio C^-Cg alkyl group, Cj-Cg alkoxycarbonyl group, phenyl group and substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-C^ alkyl group, halo C^-C^ alkyl group, C^-C^ alkoxy group, halo Cj-Cg alkoxy group, Ci-Ct; alkylthio group, halo Cj-Cg alkyl¬thio group, Ci-Cg alkylsulfinyl group, halo C,-Cg alkyl¬sulfinyl group, Cj-Cg alkylsulfonyl group, halo Cj-Cg alkyl¬sulfonyl group, mono C^-Cg alkylamino group, di Cj-Cg alkylamino group in which Ci-Cg alkyl groups may be same or different, and Ci-Cg alkoxycarbonyl group,
further, an arbitrary saturated carbon atom in said Ci-Cg alkylene group, substituted C^-Ca alkylene group, Cj-Cj alkenylene group, substituted Cj-Cj alkenylene group, Cj-Cj alkynylene group and substituted Cj-Cg alkynylene group may be substituted with a Cj-Cj alkylene group to form a Cj-C^ cycloalkane ring, and arbitrary two carbon atoms in said C,-CB alkylene group, substituted Cj^-Cg alkylene group.

Cj-Cg alkenylene group and substituted Cj-Cj alkenylene group may be taken conjointly with an alkylene group or an alkenylene group to form a Cj-C^ cycloalkane ring or Cg'^'S cy°^°" alkene ring;
R^ represents hydrogen atom, mercapto group, Cj-Cj alkylthio group, halo Ci-Cj alkylthio group, Cj-C^ cycloalkyl group, halo C^-Cj cycloalkyl group, phenyl group, substi¬tuted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cg alkyl group, halo Ci-C^ alkyl group, Ci-Cj alkoxy group, halo Ci-Cj alkoxy group, Ci-Cj alkylthio group, halo C^-C^ alkylthio group, C^-Cj alkylsulfinyl gi^oup, halo C^-Ca alkylsulfinyl group, Ci-Cg alkylsulfonyl group, halo Cj^-C^ alkylsulfonyl group, mono Ci-Cj alkylamino group, di Ci-C^ alkylamino group in which Cj-Cs alkyl groups may be same or different, and Cj-Cg alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cj alkyl group, halo Cj-C^ alkyl group, C^-C^ alkoxy group, halo C1-C4 alkoxy group, Ci-Cg alkylthio group, halo C^-Cg alkylthio group, Ci-Cj alkylsulfinyl group, halo Ci-Cj alkylsulfinyl group, Cj-Cj alkylsulfonyl group, halo Ci-Ce alkylsulfonyl group, mono Ci-Cfi alkylamino group, di Ci-C( alkylamino group in which Cj-Cj alkyl groups may be same or different, and Ci-C^ alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different

substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-Cg alkyl group, halo C,-Cj alkyl group, C^-Cs alkoxy group, halo Ci-Cj alkoxy group, Ci-Cj alkylthio group, halo Cj-Cg alkylthio group, Cj-C, alkylsulfinyl group, halo Ci-Cg alkylsulfinyl group, Cj-Cg alkylsulfonyl group, halo Cj-Cg alkylsulfonyl group, mono Cj-Cj alkylamino group, di C^-Cg alkylamino group in which Ci-Cg alkyl groups may be same or different, and Cj-Cg alkoxycarbonyl group, or -A^-R* [wherein A^ represents -C(=0)-, -ct=S)- » -C(=NR^)- (in which R* represents hydrogen atom, Ci-Cg alkyl group, Cj-Cg alkoxy group, mono Cj-Cg alkylamino group, di C^-Cg alkylamino group in which Ci-Cg alkyl groups may be same or different, Cj-Cg alkoxy¬carbonyl group, phenyl group or substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-Cg alkyl group, halo C^-Cg alkyl group, Cj-Cg alkoxy group, halo C^-Cg alkoxy group, C^-Cg alkylthio group, halo C^-Cj alkylthio group, Cj-Cg alkyl¬sulfinyl group, halo Ci-Cg alkylsulfinyl group, Ci-Cg alkylsulfonyl group, halo Cj-Cg alkylsulfonyl group, mono Cj-Cg alkylamino group, di C^-Cg alkylamino group in which Ci-Cg alkyl groups may be same or different, and Cj-Cg alkoxycarbonyl group),
CJ-CB alkylene group, halo C,-CB alkylene group, Cj-Cg alkenylene group, halo Cj-Cg alkenylene group, Cj-Cg alkynylene group or halo Cj-Cg alkynylene group; and
(1) in cases where A^ represents -C(=0)-, -C(=S)-

or -C(=NR^)- wherein R^ is as defined above, R* represents hydrogen atom, C^-C^ alkyl group, halo Cj-Cj alkyl group, Cj-Cfi cycloalkyl group, halo C^-Cg cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consist¬ing of halogen atom, cyano group, nitro group, C^-Cs alkyl group, halo c^-d alkyl group, Cj-C^ alkoxy group, halo C^-Cj alkoxy group, Cj-Cg alkylthio group, halo Cj-Cg alkylthio group, Ci-Cg alkylsulfinyl group, halo C^-Cg alkylsulfinyl group, Ci-Cg alkylsulfonyl group, halo C^-C^ alkylsulfonyl group, mono Ci-C^ alkylamino group, di Cj-Cg alkylamino group in which C^-Cg alkyl groups may be same or different, and C^-Cj alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-Cg alkyl group, halo Cj-Cg alkyl group, C^-Cg alkoxy group, halo C^-Cg alkoxy group, Ci-Cg alkylthio group, halo Ci-Cg alkylthio group, C^-Cg alkylsulfinyl group, halo C^-C^ alkylsulfinyl group, C^-Cf alkylsulfonyl group, halo Cj-Cg alkylsulfonyl group, mono Ci-Cg alkylamino group, di Cj-Cg alkylamino group in which Cj-Cg alkyl groups may be same or different, and Ci-Cj alkoxycarbonyl group, or -Z^-R* wherein z' represents -0-, -S- or -N(R')- (wherein R' represents hydrogen atom, Cj-Cg alkyl group, C,-Cg alkylcarbonyl group, halo Cj-Cg alkyl-carbonyl group or C^-Cg alkoxycarbonyl group), and R* represents hydrogen atom, Cj^-Cg alkyl group, halo Cj-C^ alkyl group, Cj-Cg alkenyl group, halo Cj-Cg alkenyl group, Cj-Cg

alkynyl group, halo C^-c^ alkynyl group, Cj-Cg cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo C^-C^ alkyl group, C^-Cs alkoxy group, halo Ci-Cj alkoxy group, Ci-Cs alkylthio group, halo C^-C^ alkylthio group, C^-Cg alkylsulfinyl group, halo Ci-C^ alkylsulfinyl group, Cj-C^ alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono Ci-C^ alkylamino group, di C1-C5 alkylamino group in which Cj-Cg alkyl groups may be same or different, and Cj-C^ alkoxycarbonyl group, phenyl C^-C, alkyl group, substituted phenyl C^-C, alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-C^ alkyl group, halo Ci-C^ alkyl group, Ci-Cg alkoxy group, halo Cj-Cg alkoxy group, Ci-Cg alkylthio group, halo Cj-Cc alkylthio group, C^-Cj alkyl-sulfinyl group, halo C^-C^ alkylsulfinyl group, C^-Cj alkylsulfonyl group, halo Cj-Cg alkylsulfonyl group, mono Ci-Cg alkylamino group, di Cj-C^ alkylamino group in which Ci-C|s alkyl groups may be same or different, and Ci-C^ alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cg alkyl group, halo Cj-Cg alkyl group, Cj-Cg alkoxy group, halo Ci-Cg alkoxy group, Ci-Cj alkylthio group, halo Ci-C^ alkylthio group, Cj-Ce alkylsulfinyl group, halo C^-Cg alkylsulfinyl group, Ci-Cg

alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono C^-Cs alkylamino group, di C^-Cs alkylamino group in which Ci^-Cj alkyl groups may be same or different, and Ci-Cj alkoxycarbonyl group, and
(2) in cases where A' represents C^-Cg alkylene group, halo Ci-Cg alkylene group, Cj-C^ alkenylene group, halo Cj-C^ alkenylene group, Cj-Cj alkynylene group or halo C3-C5 alkynylene group, R' represents hydrogen atom, halogen atom, cyano group, nitro group, Cj-C^ cycloalkyl group, halo Cj-Cj cycloalkyl group, Ci-Cs alkoxycarbonyl group, mono Cj-Cj alkylaminocarbonyl group, di Ci-C^ alkylaminocarbonyl group in which C^~c^ alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consist¬ing of halogen atom, cyano group, nitro group, C,-Cg alkyl group, halo Ci-C^ alkyl group, Ci-C^ alkoxy group, halo Ci-Cj alkoxy group, Ci-Cj alkylthio group, halo C^-Cj alkylthio group, Ci-C^ alkylsulfinyl group, halo Cj-Cg alkylsulfinyl group, C^-C^ alkylsulfonyl group, halo C^-Cg alkylsulfonyl group, mono Ci-Cj alkylamino group, di C^~C^ alkylamino group in which C^-Cj alkyl groups may be same or different, and Ci-Cj alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-Ce alkyl group, halo Cj-Cg alkyl group, C1-C5 alkoxy group, halo Ci-Cj alkoxy group, Ci-Cg alkylthio group, halo c^-c^ alkylthio group, C^-Cj alkylsulfinyl group, halo Ci-Cg alkylsulfinyl group, Ci-Cg

alkylsulfonyl group, halo Cj-Ce alkylsulfonyl group, mono Cj-Cj alkylamino group, di C^-C^ alkylamino group in which Cj-C^ alkyl groups may be same or different, and C^-Cs alkoxycarbonyl group, or -Z^-R* wherein Z' represents -0-, -S-, -SO-, -SOj-, -N(R')- (wherein R' represents hyd:i:ogen atom, Ci-Cj alkyl group, Cj-C^ alkylcarbonyl group, halo C^-Cg alkylcarbonyl group, Ci-C^ alkoxycarbonyl group, phenyl-carbonyl group, or substituted phenylcarbonyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cg alkyl group, halo C^-Cj alkyl group, Cj-Cs alkoxy group, halo C^-Cf, alkoxy group, Cj-C^ alkylthio group, halo Ci-Cg alkylthio group, C^-C^ alkylsulfinyl group, halo Ci-C^ alkylsulfinyl group, C^-C^ alkylsulfonyl group and halo C^-C^ alkylsulfonyl group), -C(=0)- or -C(=N0R")- {wherein R'" represents hydrogen atom, Cj-Cj alkyl group, halo C^-C^ alkyl group, Cj-Cg alkenyl group, halo Cj-C^ alkenyl group, C^-C^ alkynyl group, halo C^-C^ alkynyl group, C3-C5 cycloalkyl group, phenyl Cj-C, alkyl group or substituted phenyl Ci-C, alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consist¬ing of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo C^-C^ alkyl group, Ci-Cg alkoxy group, halo C^-C^ alkoxy group, Ci-Cg alkylthio group, halo Ci-C^ alkylthio group, Ci-Cj alkylsulfinyl group, halo C^-C^ alkylsulfinyl group, Ci-Cg alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono C^-Cg alkylamino group, di C^-Cj alkylamino group in which C^-Ce alkyl groups may be same or different, and

Ci-Cj alkoxycarbonyl group) and R^ represents hydrogen atom, Ci-Cj alkyl group, halo Ci-C^ alkyl group, C^-c^ alkenyl group, halo Cj-C^ alkenyl group, C^-Cg alkynyl group, halo Cj-Cj alkynyl group, C-^-C^ cycloalkyl group, Cj-Ce alkyl-carbonyl group, halo Ci-Cg alkylcarbonyl group, C^-Cj alkoxycarbonyl group, mono Ci-Cj alkyiaminocarbonyl group, di Ci-Cg alkyiaminocarbonyl group in which Cj-Cg alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano .group, nitro group, Cj-C^ alkyl group, halo Cj-Ce alkyl group, Cj^-C^ alkoxy group, halo C^-Cg alkoxy group, C,-Cg alkylthio group, halo Ci-C^ alkylthio group, Cj-Cg alkyl-sulfinyl group, halo C^-C^ alkylsulfinyl group, C^-C^ alkylsulfonyl group, halo C^-C^ alkylsulfonyl group, mono C^'C^ alkylamino group, di C^-Cis alkylamino group in which Ci-Cj alkyl groups may be same or different, and Cj-Cg alkoxycarbonyl group, phenyl Cj-C^ alkyl group, substituted phenyl C^-C^ alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C,-Cj alkyl group, halo Ci-Cc alkyl group, Ci-C^ alkoxy group, halo Ci-Cj alkoxy group, c^-c^ alkylthio group, halo Ci-C^ alkylthio group, Cj-Cj alkylsulf inyl group, halo Ci-C^ alkylsulfinyl group, C^-C^ alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono Cj-Cg alkylamino group, di C-^-C^ alkylamino group in which Cj-Cg alkyl groups may be same or different, and C^-Cs alkoxycarbonyl group, heterocyclic

group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo Cj-Cg alkyl group, Ci-C^ alkoxy group, halo Ci-Cg alkoxy group, C^-C^ alkylthio group, halo Cj-Cg alkyl-thio group, C^-C^ alkylsulfinyl group, halo Ci-C^ alkyl-sulfinyl group, C^-Cj alkylsulfonyl group, halo Cj-Cj alkylsulfonyl group, mono Ci-C^ alkylamino group, di Ci-C^ alkylamino group in which Cj-Ct; alkyl groups may be same or different, and C^-C^ alkoxycarbonyl group], or
alternatively, R^ may be combined with A^ to form a 5- to 8-membered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms;
R^ and R' which may be same or different, represent hydrogen atom, Cj-C^ cycloalkyl group or -A^-R' wherein A' and R' are as defined above; or
alternatively, R' may be combined with A' or R^ to form a 5- to 7-meml3ered ring which may be intercepted by 1 or 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms;
X which may be same or different, represents halogen atom, cyano group, nitro group, C^-C^ cycloalkyl group, halo C^-C^ cycloalkyl group, C^-Cg alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-Cg alkyl group, halo C^-C^ alkyl group, Cj-C^ alkoxy group.

halo Ci-Cj alkoxy group, C^-c^ alkylthio group, halo C^-C^ alkylthio group, Ci-C^ alkylsulfinyl group, halo C^-Cj alkylsulfinyl group, Cj-C^ alkylsulfonyl group, halo Cj-C^ alkylsulfonyl group, mono Cj-Cj alkylamino group, di C^-Cg alkylamino group in which Cj-Cj alkyl groups may be same or different, and Ci-C^ alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo Cj-Ce alkyl group, Cj-Cj alkoxy group, halo C^-Cj alkoxy group, Ci-C^ alkylthio group, halo Ci-Cs alkyl¬thio group, Ci-Cj alkylsulfinyl group, halo Ci-C^ alkyl¬sulfinyl group, C^-Cs alkylsulfonyl group, halo Cj-Cg alkylsulfonyl group, mono Cj-Cj alkylamino group, di C^-C^ alkylamino group in which C^-C^ alkyl groups may be same or different, and Ci-C^; alkoxycarbonyl group, or -A^-R*^^ [wherein A' represents -0-, -S-, -SO-, -so^-, -C(=0)-, -C(=NOR")- (in which R'-^ represents hydrogen atom, Cj-C^ alkyl group, halo Ci-Cj alkyl group, c^-c^ alkenyl group, halo Cj-C^ alkenyl group, Cj-Cg alkynyl group, Cj-C^ cycloalkyl group, phenyl C1-C4 alkyl group or substituted phenyl C^-C^ alkyl group having, on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cg alkyl group, halo Ci-C^ alkyl group, C^-Cj alkoxy group, halo Ci-C^ alkoxy group, 0,-0^ alkylthio group, halo Cj-Cg alkylthio group, Ci-Cg alkylsulfinyl group, halo Ci-Cg alkylsulfinyl group, Ci-Cj alkylsulfonyl group, halo Cj-Cj alkylsulfonyl

group, mono Ci-C^ alkylamino group, di C^-C^ alkylamino group in which Ci-Cg alkyl groups may be same or different, and Ci-Cj alkoxycarbonyl group), C^-Cf alkylene group, halo C^-C^ alkylene group, Cj-Cg alkenylene group, halo Cj-C^ alkenylene group, Cj-Cj alkynylene group or halo Cj-C^ alkynylene group; and
(1) in cases where A^ represents -0-, -S-, -SO- or -SO,-, R^^ represents halo Cj-C^ cycloalkyl group, halo Cj-C^ cycloalkenyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-Cf, alkyl group, halo C1-C5 alkyl group, Ci-Cg alkoxy group, halo C^-Cj alkoxy group, Ci-Cg alkylthio group, halo C^-C^ alkylthio group, Cj-Cg alkyl-sulfinyl group, halo C^-Cs alkylsulfinyl group, C1-C5 alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono Ci-Cj alkylamino group, di C^-Cs alkylamino group in which Ci-Cj alkyl groups may be same or different, and C^-C^ alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-Cj alkyl group, halo Ci-Cg alkyl group, Cj-C^ alkoxy group, halo C^-C^ alkoxy group, Ci-Cd alkylthio group, halo Ci-Cg alkylthio group, Ci-C^ alkylsulfinyl group, halo Cj-Cg alkylsulfinyl group, Cj-Cg alkylsulfonyl group, halo Ci-Cc alkylsulfonyl group, mono Ci-Cj alkylamino group, di Ci-C^ alkylamino group in which Ci-Cg alkyl groups may be same or different, and Ci-Cj

alkoxycarbonyl group, or -A*-R^^ (wherein A* represents Cj-Ct, alkylene group, halo Cj-C^ alkylene group, Cj-C, alkenylene group, halo Cj-Cg alkenylene group, Cj-Cg alkynylene group or halo Cj-Cj alkynylene group, and R'^ represents hydrogen atom, halogen atom, C^-Cg cycloalkyl group, halo Cj-C^ cycloalkyl group, C^-C^ alkoxycarbonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-C^ alkyl group, halo C^-C^ alkyl group, Ci-Cg alkoxy group, halo Cj-C^ alKoxy group, Cj-Cg alkylthio group, halo C^-C^ alkylthio group, Ci-C^ alkylsulfinyl group, halo Ci-Cj alkylsulfinyl group, C,-Cg alkylsulfonyl group, halo Ci-Cg alkylsulfonyl group, mono Cj-C^ alkylamino group, di C^-Cj alkylamino group in which Ci-C^ alkyl groups may be same or different, and Ci-Cj alkoxycarbonyl group, or -A^-R^* (wherein A^ represents -0-, -S-, -SO-, -SO2- or -C(=0)-, and R" represents Cj-Cj alkyl group, halo Ci-C^ alkyl group, Cj-Cg alkenyl group, halo Cj-Cg alkenyl group, C^-Cg alkynyl group, halo Cj-C^ alkynyl group, C^-Cg cycloalkyl group, halo C^-C^ cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-Cg alkyl group, halo C^-Ce alkyl group, C^-C^ alkoxy group, halo C^-Cg alkoxy group, C^-C^ alkylthio group, halo Cj-Cg alkylthio group, Ci-C^ alkylsulfinyl group, halo Cj-Cg alkyl¬sulfinyl group, Ci-Cg alkylsulfonyl group, halo Cj-C^ alkyl¬sulfonyl group, mono C^-C^ alkylamino group, di Cj-Cg

alkylamino group in which Cj-C^ alkyl groups may be same or different, and Ci-Cj alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo Cj-C^ alkyl group, Cj-Cg alkoxy group, halo C1-C5 alkoxy group, Cj-Cg alkylthio group, halo Ci-C^ alkyl-thio group, Ci-Cj alkylsulfinyl group, halo C^-C^ alkyl-sulfinyl group, Cj-Cj alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono C^-C^ alkylamino group, di Cj-Cj alkylamino group in which Cj-Cj alkyl groups may be same or different, and Cj-C^ alk.oxycarbonyl group)), and
(2) in cases where A' represents -C{=0)- or -C(=NOR^^)- wherein R^^ is as defined above, R" represents hydrogen atom, Cj-Cj alkyl group, halo C^-Cj alkyl group, Cj-Cg alkenyl group, halo Cj-Cg alkenyl group, Cj-C^ cyclo-alkyl group, halo Cj-Cg cycloalkyl group, Ci-C^ alkoxy group, Cj-Cj alkylthio group, mono C^-Cj alkylamino group, di Cj-C^ alkylamino group in which Ci-C^ alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-C^ alkyl group, halo Ci-C^ alkyl group, C^-Cg alkoxy group, halo Ci-Cj alkoxy group, Cj-Cti alkylthio group, halo C^-Cg alkylthio group, C^-C^ alkylsulfinyl group, halo Cj-Cj alkylsulfinyl group, Cj-Cg alkylsulfonyl group, halo Ci-Cg alkylsulfonyl group, mono C^~C^ alkylamino group, di Cj-Cg alkylamino group in which C^-C^ alkyl groups may be same or

different, and C^-Cg alkoxycarbonyl group, phenylamino group, substituted phenylamino group having on the ring thereof, at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-C^ alkyl group, halo Cj-C^ alkyl group, Cj-Cs alkoxy group, halo Cj-C^ alkoxy group, C^-Cs alkylthio group, halo Cj-Cj alkylthio group, Cj-Cg alkyl-sulfinyl group, halo Ci-C^ alkylsulfinyl group, C^-C^ alkylsulfonyl group, halo C^-Cj alkylsulfonyl group, mono Cj-Cj alkylamino group, di Ci-Cj alkylamino group in which C1-C5 alkyl groups may be same or different, and C^-Cg alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-C^ alkyl group, halo Ci-C^ alkyl group, Cj-Cg alkoxy group, halo Ci-Cg alkoxy group, Ci-Cg alkylthio group, halo C^-Cg alkylthio group, Ci-Cg alkylsulfinyl group, halo Cj-Cg alkylsulfinyl group, Cj-Cg alkylsulfonyl group, halo C,-Cg alkylsulfonyl group, mono Ci-Cg alkylamino group, di C^-C^ alkylamino group in which Ci-Cg alkyl groups may be same or different, and C^-C^ alkoxycarbonyl group, and
(3) in cases where A^ represents Cj-Cg alkylene group, halo Ci-Cg alkylene group, Cj-Cg alkenylene group, halo Cj-Cg alkenylene group, Cj-Cg alkynylene group or halo C^-Cg alkynylene group, R^^ represents hydrogen atom, hydroxy group, halogen atom, Cj-Cg cycloalkyl group, halo C3-C5 cycloalkyl group, Ci-Cj alkoxycarbonyl group, phenyl group.

substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-C^ alkyl group, halo Ci-Cg alkyl group, C^-Cj alkoxy group, halo Cj-C^ alkoxy group, Ci-Cj alkylthio group, halo Ci-C^ alkylthio group, Ci-Cg alkylsulfinyl group, halo C^-C^ alkylsulfinyl group, Ci-Cs alkylsulfonyl group, halo C^-Cj alkylsulfonyl group, mono Ci-C^ alkylamino group, di Ci-C^ alkylamino group in which Ci-C^ alkyl groups may be same or different, and Cj-Cj alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cj alkyl group, halo C^-Cg alkyl group, Cj-Cg alkoxy group, halo Cj-C^ alkoxy group, C^~C^ alkylthio group, halo Cj-Cg alkylthio group, Cj-Cg alkylsulfinyl group, halo Ci-Ce alkylsulfinyl group, Cj-Cg alkylsulfonyl group, halo C^-Cg alkylsulfonyl group, mono Ci-Cg alkylamino group, di Ci-C^ alkylamino group in which Ci-Cg alkyl groups may be same or different, and Ci-C^ alkoxycarbonyl group, or -A*-R'^ (wherein A* represents -0-, -S-, -SO- or -SOj-, and R^^ represents Cj-Cg cycloalkyl group, halo Cj-Cg cycloalkyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-Cg alkyl group, halo Cj-Cg alkyl group, Cj-Cg alkoxy group, halo Cj-Cg alkoxy group, Ci-Cg alkylthio group, halo C^-C^ alkylthio group, Ci-C^ alkylsulfinyl group, halo Ci-C^ alkylsulfinyl group, Ci-Cg

alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono C^-Cs alkylamino group, di C^-Cj alkylamino group in which Ci-Cj alkyl groups may be same or different, and C1-C5 alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo C-^-Cf, alkyl group, Ci-C^ alkoxy group, halo Ci-C^ alkoxy group, Ci-Cg alkylthio group, halo Ci-C^ alkylthio group, c^-c^, alkylsulfinyl group, halo Ci-C^ alkylsulfinyl group, Ci-C^ alkylsulfonyl group, halo C1-C5 alkylsulfonyl group, mono C^-Cg alkylamino group, di Ci-C^ alkylamino group in which Ci-Cj alkyl groups may be same or different, and Cj-C^ alkoxycarbonyl group, or -A^-R'* {wherein A' represents Cj-C^ alkylene group, halo Ci-C^ alkylene group, Cj-C^ alkenylene group, halo Cj-Cj alkenylene group, C^-Cg alkynylene group or halo Cj-Cg alkynylene group, and R" represents hydrogen atom, halogen atom, Cj-Cj cycloalkyl group, halo Cj-Cg cycloalkyl group, Ci-C^ alkoxy group, halo C^-Cj alkoxy group, C^-Cj alkylthio group, halo Cj-Cg alkylthio group, Ci-Cg alkylsulfinyl group, halo C^-C^ alkylsulfinyl group, Cj-Cj alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cg alkyl group, halo Cj-Cg alkyl group, Cj-Cj alkoxy group, halo Cj-Cg alkoxy group, C^-Cg alkylthio group, halo Cj-Cg alkyl¬thio group, Ci-Cj alkylsulfinyl group, halo Cj-Cj alkyl-

sulfinyl group, C^-Ce alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono C^-Cj alkylamino group, di Ci-Cj alkylamino group in which Ci-C^ alkyl groups may be same or different, and C^-Cf, alkoxycarbonyl group, phenoxy group, substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-C^ alkyl group, halo c^-c^ alkyl group, Cj-Cg alkoxy group, halo C^-C^ alkoxy group, Cj-Cg alkylthio group, halo C^-C^ alkylthio group, Ci-Cg alkylsulfinyl group, halo Ci-Cj alkylsulfinyl group, Ci-Cg alkylsulfonyl group, halo C^-Cg alkylsulfonyl group, mono Ci-Cg alkylamino group, di Ci-C^ alkylamino group in which Cj-Cg alkyl groups may be same or different, and C1-C5 alkoxycarbonyl group, phenylthio group, substituted phenylthio group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-Cg alkyl group, halo Ci-C^ alkyl group, Cj-Cg alkoxy group, halo C^-Cg alkoxy group, Cj-Ce alkylthio group, halo C^-Cg alkylthio group, Cj-Cg alkylsulfinyl group, halo Cj-Cg alkylsulfinyl group, Cj-Cg alkylsulfonyl group, halo C^-Cg alkylsulfonyl group, mono Ci-Cg alkylamino group, di Cj-Cg alkylamino group in which Ci-Cg alkyl groups may be same or different, and Cj-Cg alkoxycarbonyl group, heterocyclic group, or substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-Cg alkyl group, halo C^-Cg alkyl group, Ci-C^ alkoxy group, halo Ci-Cg alkoxy group.

Ci-Cj alkylthio group, halo C^-C^ alkylthio group, C^-C^ alkylsulfinyl group, halo Ci-Cg alkylsulfinyl group, Cj-Cj alkylsulfonyl group, halo C^~c^ alkylsulfonyl group, mono Ci-Cj alkylamino group, di Cj-Cj alkylamino group in which Cj-Cg alkyl groups may be same or different, and Cj-Ce alkoxycarbonyl group))]; and 1 represents an integer of 0 to 4; and
alternatively, X may be taken conjointly with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo Cj-C^ alkyl group, Cj-Cg alkoxy group, halo Ci-C^ alkoxy group, Ci-Cg alkylthio group, halo Cj-C^ alkylthio group, Ci-Cj alkylsulfinyl group, halo C^-Cj alkylsulfinyl group, Ci-Cg alkylsulfonyl group, halo Cj-Cj alkylsulfonyl group, mono C^-C^ alkylamino group, di Cj-C^ alkylamino group in which C^-Cg alkyl groups may be same or different, and C^-Ct; alkoxycarbonyl group; and
Y may be same or different and represents halogen atom, cyano group, nitro group, halo Cj-Cg cycloalkyl group, tri Ci-Cj alkylsilyl group in which Ci-Cc alkyl groups may be same or different, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Ci-C^ alkyl group, halo C^-Cg alkyl group, Ci-Ce alkoxy group, halo Cj-Cj alkoxy group, C^-Cg alkylthio group, halo C^-C^ alkylthio group, Cj^-C^ alkyl-

sulfinyl group, halo Cj-Cd alkylsulfinyl group, C^-C^ alkylsulfonyl group, halo C^-C^ alkylsulfonyl group, mono Cj-Cg alkylamino group, di Cj-Cg alkylamino group in which C^-C^ alkyl groups may be same or different, and C^-Cf, alkoxycarbonyl group, heterocyclic group, substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cg alkyl group, halo C^-c^ alkyl group, Cj-Cg alkoxy group, halo C^-C^ alkoxy group, Cj-Cg alkylthio group, halo Ci-C^ alkylthio group, Ci-Cg alkylsulfinyl group, halo C^-C^ alkylsulfinyl group, Cj-C^ alkylsulfonyl group, halo C^-Cg alkylsulfonyl group, mono Ci-Cg alkylamino group, di Cj^-C^ alkylamino group in which Ci-Cj alkyl groups may be same or different, and C^-C^ alkoxycarbonyl group, or -A^-R" wherein A' and R" are as defined above; and m represents an integer of 0 to 5; and
Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom, Ci^-Ce alkyl group, halo Ci-C^ alkyl group, C^-C^ alkoxy group, halo C^-Cg alkoxy group, Ci-Cu alkylthio group, halo Ci-C^ alkylthio group, Cj-Cg alkylsulfinyl group, halo Ci-Cg alkylsulfinyl group, C^-Cg alkylsulfonyl group, halo C^-Cg alkylsulfonyl group, phenyl group, substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, Cj-Cg alkyl group, halo Ci-C^ alkyl

group, Ci-C(; alkoxy group, halo C^-Cf alkoxy group, C^-Cj alkylthio group, halo C^-c^ alkylthio group, Cj-C^ alkyl-sulfinyl group, halo Cj-C^ alkylsulfinyl group, C^-Cj alkylsulfonyl group, halo Cj-Cd alkylsulfonyl group, mono Ci-Cj alkylamino group, di C^-C^ alkylamino group in which Ci-Cd alkyl groups may be same or different, and C^-C^ alkoxycarbonyl group, heterocyclic group, and substituted heterocyclic group having at least one, same or different substituents selected from the group consisting of halogen atom, cyano group, nitro group, C^-Ce alkyl group, halo Cj-Cg alkyl group, Cj-Cc alkoxy group, halo C^-Cg alkoxy group, Cj-Cj alkylthio group, halo Ci-C^ alkylthio group, Ci-C^ alkylsulfinyl group, halo Cj-Cg alkylsulfinyl group, Cj-Cg alkylsulfonyl group, halo Ci-C^ alkylsulfonyl group, mono Cj-Cg alkylamino group, di C^-C^ alkylamino group in which Cj-Cg alkyl groups may be same or different, and Cj-C^ alkoxycarbonyl group; and
n represents an integer of 0 to 2;
provided that when X, R^ and R^ simultaneously represent hydrogen atom, m represents an integer of 2, Y of the 2-position represents fluorine atom and Y of the 3-position represents chlorine atom, then A' is not propylene group, R^ is not methyl group and n is not an integer of 0.
In the definition of the general formula (I) representing the phthalamide derivative of the present invention, the term "halogen atom" means chlorine atom, bromine atom, iodine atom or fluorine atom; the term "Ci-Cj alkyl" means a straight or branched chain alkyl group

having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl and the like; the term "halo Cj-Cg alkyl" means a straight or branched chain alkyl group having 1 to 6 carbon atoms which may be substituted with at least one, same or different halogen atoms; the term "Ci-Cg alkylene" means a straight or branched chain alkylene group having 1 to 8 carbon atoms such as methylene, ethylene, propylene, trimethylene, dimethylmethylene, tetramethylene, isobutylene, dimethylethylene, octamethylene and the like; the term "a 5- to 8- or 5- to 7-membered ring which may be intercepted by 1 to 2, same or different oxygen atoms, sulfur atoms or nitrogen atoms formed by R^ with A^ or R^ with A^ or R^" means, for example, perhydrothiazine ring, thiazolidine ring, thiazetidine ring, dihydrothiazine ring, thiazoline ring, perhydroxathiazine ring, dihydroxathiazine ring, dithiazine ring, perhydrodithiazine ring, and the like.
The term "heterocyclic group" means 5- to 6-membered heterocyclic group having one or more same or different hetero atoms selected from oxygen atoms, sulfur atoms or nitrogen atoms such as pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group, tetrahydro-furyl group, thienyl group, tetrahydrothienyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, imidazolyl group, trithiazolyl group, pyrazolyl group, and

the like. As the "fused ring", there can be exemplified naphthalene, tetrahydronaphthalene, indene, indane, quinoline, quinazoline, indole, indoline, coumarone, isocoumarone, benzodioxane, benzodioxole, benzofuran, dihydrobenzofuran, benzothiophene, dihydrobenzothiophene, benzoxazole, benzothiazole, benzimidazole, indazole, and the like.
As a salt of a phthalamide derivative represented by the general formula (!) of the present invention, there can be exemplified inorganic acid salt such as hydro-chlorate, sulfate, nitrate, phosphate and the likej organic acid salt such as acetate, fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and the like; and salt of metallic ion such as sodium ion, potassium ion, calcium ion and the like.
Some of the phthalamide derivatives represented by the general formula (I) of the present invention contain an asymmetric carbon atom or an asymmetric center in the structural formula thereof, and in some cases there can exist two optical isomers. The present invention includes all these optical isomers and all the mixtures consisting of arbitrary proportions of these optical isomers.
Preferable examples of each substituent of the phthalamide derivative of general formula (I) or salt thereof of the present invention are A^ is a straight or branched Ci-Cg alkylene group; R^ is C^-C^ alkyl group or halo Cj-Cj; alkyl group; each of R^ and R^ is hydrogen atom or Ci-C^ alkyl group; X is halogen atom, nitro group, C^~C^ alkyl


wherein R^, R% A', X, Y, 1, m and n are as defined above. A phthalic anhydride derivative of the general formula (V) is reacted with an aniline of the general formula {IV) in the presence of an inert solvent to obtain a phthalimide derivative of the general formula (III). The phthalimide derivative (III) is reacted with an amine of

the general formula (II) after or without being isolated, whereby a phthalamide derivative of the general formula (I-l) can be produced. (1) General formula (V) -> general formula (III)
As the inert solvent used in this reaction, any solvent may be used so long as it does not mar)cedly inhibit the progress of the reaction. There can be exemplified aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., chlorinated aromatic hydrocarbons such as chlorobenzene, dichloro-benzene, etc.; acyclic or cyclic ethers such as diethyl ether, dioxane, tetrahydrofuran, etc., esters such as ethyl acetate, etc.; amides such as dimethylformamide, dimethyl-acetamide, etc.; acids such as acetic acid, etc.; dimethyl sulfoxide; and 1,3-dimethyl-2-imidazolidinone. These inert solvents may be used alone or as a mixture thereof.
Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though either of them may be used in excess. If necessary, the reaction may be carried out under dehydrat¬ing conditions.
As to the reaction temperature, the reaction can be carried out in a temperature range of room temperature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 4 8 hours.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromato¬graphy, etc., whereby the desired compound can be produced. The desired compound can be subjected to the subsequent reaction without isolation from the reaction solution.
The phthalic anhydride derivative of the general formula (V) can be produced by the process described in J. Org. Chem., 52, 129 {1987), J. Am. Chem. Soc, ^, 1865 (1929), J. Am. Chem. Soc, 61, 1542 (1941), etc. The aniline of the general formula (IV) can be produced by the process described in J. Org. Chem., 19., 1 (1964), Angew. Chem, int. Ed. Engl., 21^ 871 (1985), Synthesis, HM' ^67, Bulletin of the Chemical Society of Japan, 1973. 2351, DE-2606982, JP-A-1-90163, etc. (2) General formula (III) -* general formula (I-l)
In this reaction, there can be used the inert solvents exemplified above as the inert solvent used in the reaction (1).
Since the reaction is an equimolar reaction, it is sufficient that the reactants are used in equimolar amounts, though the amine of the general formula (IJ) may be used in excess.
As to the reaction temperature, the reaction can be carried out in a temperature range of room tempeirature to the reflux temperature of the inert solvent used. Although the reaction time is varied depending on the scale

of reaction, the reaction temperature, etc., it may be properly chosen in a range of several minutes to 48 hours.
After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromato¬graphy, etc., whereby the desired compound can be produced. Production process 2
a')i 0 an o

II \ li .
'I II
0 0
m
cni-n ciii)
CO)n
A^-ts^ CO)n


CIII) ^O^^C
II 0

-NH-^gj^

CI-1)
wherein R^ R% A', X, Y, 1, m and n are as defined above, X' is a halogen atom or a nitro group, provided that X is other than a hydrogen atom or a nitro group.
A phthalimide derivative of the general formula (III-l) is reacted with a reactant corresponding to X in the presence of an inert solvent to obtain a phthalimide

derivative of the general formula (III). The phthalimide derivative (III) is reacted with an amine of the general formula (II) after or without being isolated, whereby a phthalamide derivative of the general formula (I-l) can be produced.
(1) General formula (III-l) -^ general formula (III)
This reaction can be carried out according to the methods described in J. Org. Chem., 42, 3415 (1977), Tetrahedron, 25, 5921 (1969), Synthesis, 1984, 667, Chem. Lett., 1973. 471, J. Org. Chem., 11, 3318 (1974), J. Org. Chem., 19, 3327 (1974), etc.
(2) General formula (III) -* general formula (I-l)
This reaction can be carried out according to production process l-(2).

Production process 3


I + 1
a)m
Hg^
CO)n t S-
2
HN-R (ID

CX)1

/

HN(R CIV)





CX)1
CY)Bi
cni-4)
CR^-E)
Condensing. agent
(1)1
CY)m
CTI)
CO)n
1 ^ 1 0 A^-S-R^
H I «
C-N-R'^
C-OH
II
0
Condensing agent
(Y)B
HNCR^ CIV)
(0)n
1 ^ I

CY)


an
0

II
C-OH
C-HOC
II 0
Condensing ,,., (.>
agent uii-s;
CO)n
f S-
2
1 + 1
(R^-H)
HN-R
on
Condensing
agent



BN(R^)
CIV)

(Y)D

CX)1

CO)n 0 A^-S-R^
C-N-R'
C-NCR'
II
0
0)

g)B

(0)n 1^ 1
' 2 CIO

wherein R^, R% R% A\ X, Y, 1, m and n are as defined above.
A phthalic anhydride derivative of the general formula (V) is reacted with an amine of the general formula
i (II) in the presence of an inert solvent to obtain a phthalamic acid of the general formula (III-4). The phthalamic acid (III-4) is treated as follows after or without isolation, when R^ of the phthalamic acid (III-4) is a hydrogen atom, the phthalamic acid (III-4) is
I condensed into a compound of the general formula (VI) in the presence of a condensing agent, and the compound (VI) is reacted with an aniline of the general formula {IV') in the presence of an inert solvent after or without being isolated. When R^ of the phthalamic acid (III-4) is other than a hydrogen atom, the phthalamic acid (III-4) is condensed with an aniline of the general formula {IV) in the presence of a condensing agent. Thus, a phthalamide derivative of the general formula (I) can be produced.
Alternatively, a phthalic anhydride derivative of the general formula (V) is reacted with an aniline of the general formula (IV) in the presence of an inert solvent to obtain a phthalamic acid of the general formula (111-5). The phthalamic acid (III-5) is treated as follows after or without isolation. When R^ of the phthalamic acid {III-5) is a hydrogen atom, the phthalamic acid (111-5) is condensed into a compound of the general formula (VI-1) in the presence of a condensing agent, and the compound (VI-1) is reacted with an amine of the general formula (II) in the

presence of an inert solvent after or without being isolated, when R^ of the phthalamic acid (III-5) is other than a hydrogen atom, the phthalamic acid (Ill-S) is condensed with an amine of the general formula (II) in the presence of a condensing agent. Thus, a phthalamide derivative of the general formula (I) can be produced.
(1) General formula (V) or general formula (Vl-1) -»
general formula (III-4) or general formula (I),
respectively
The desired compound can be produced by this reaction in the same manner as in production process l-{2).
(2) General formula {III-4) or general formula (III-5) ->
general formula (VI) or general formula (VI-1),
respectively
The desired compound can be produced by this reaction according to the method described in J. Med. Chem., la, 982 (1967).
(3) General formula (VI) or general formula (V) -^
general formula (I) or general formula {III-5),
respectively
The desired compound can be produced by this reaction in the same manner as in production process l-{2).
(4) General formula {III-4) or general formula (III-5) -^
general formula (l)
The desired compound can be produced by reacting the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5) with the aniline of the general formula (IV) or the amine of the general

formula (II), respectively, in the presence of a condensing agent and an inert solvent. If necessary, the reaction can be carried out in the presence of a base.
The inert solvent used in the reaction includes, for example, tetrahydrofuran, diethyl ether, dioxane, chloroform and dichloromethane. As the condensing agent used in the reaction, any condensing agent may be used so long as it is used in usual amide synthesis. The condens¬ing agent includes, for example, Mukaiyama reagent (e.g. 2-chloro-N-methylpyridinium iodide), 1,3-dicyclohexyl-carbodiimide (DCC), carbonyldiimidazole (CDI) and diethyl phosphorocyanidate (DEPC). The amount of the condensing agent used may be properly chosen in a range of 1 mole to excess moles per mole of the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5).
As the base usable in the reaction, there can be exemplified organic bases such as triethylamine, pyridine, etc. and inorganic bases such as potassium carbonate, etc. The amount of the base used may be properly chosen in a range of 1 mole to excess moles per mole of the phthalamic acid derivative of the general formula (III-4) or the general formula (III-5).
As to the reaction temperature, the reaction can be carried out in a temperature range of 0°C to the boiling point of the inert solvent used. Although the reaction time is varied depending on the scale of reaction, the reaction temperature, etc., it ranges from several minutes to 48 hours.

After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method, and if necessary, purified by recrystallization, column chromato¬graphy, etc., whereby the desired compound can be produced. production Process 4






the description of J. Org. Chem. 32, 3069 (1967), etc.
(2) General formula (ViII-1) or general formula (viii-2)
-> general formula (I)
The desired compound can be produced by convert¬ing a benzamide of the general formula (VlII-1) or {Vlll-2) into an ortho-lithio compound according to the description of J. org. Chem. 21, 853 (1964) and then reacted with an isocyanate of the general formula (lx-1) or (lx-2) at a temperature of -80°C to room temperature, whereby the desired compound can be produced.
(3) General formula (Vlll-1) or general formula (VllI-2)
-> general formula {III-4') or general formula
(III-5'), respectively
The desired compound can be produced by the same :onversion into an ortho-lithio compound as in (2), iollowed by introduction of carbon dioxide at a temperature if -80°C to room temperature.
After completion of the reaction, the desired ompound is isolated from the reaction solution by the onventional method and, if necessary, purified by ecrystallization, column chromatography, etc., whereby the esired compound can be produced.
4) General formula (III-4') or general formula (III-5') -> general formula (I)
The desired compound can be produced by the same rocedure as in production process 3-(l) to (4).


wherein R', R% R% h\ X, Y, 1, m and n are as defined above, provided that n cannot be an integer of 0,
A phthalamide derivative of the general formula (1-2) is reacted with an oxidant in the presence of an inert solvent, whereby a phthalamide derivative of the general formula (1-3) can be produced.
As the inert solvent used in this reaction, there can be exemplified halogenated hydrocarbons such as dichloromethane, chloroform, etc, aromatic hydrocarbon such as toluene, xylene, etc., acids such as acetic acid, etc., and alcohols such as methanol, ethanol, propanol, etc.
As the oxidant, there can be exemplified m-chloroperbenzoic acid, peracetic acid, potassium metaperiodate, potassium hydrogen persulfate (Oxen), hydrogen peroxide, etc. The amount of the oxidant may be properly selected in the range of 0.5 to 3 equivalents per equivalent of the phthalic acid diamide derivative of the general formula (1-2).
AS to the reaction temperature, the reaction can

be carried out in a temperature range of -50°C to the boiling temperature zone of the inert solvent used. Though the reaction time is varied depending on the reaction temperature and scale of the reaction, it is in the range i of several minutes to 24 hours.
After completion of the reaction, the desired compound is isolated from the reaction solution containing the desired compound by a conventional method and, if necessary, purified by recrystallization, column chromato¬graphy, etc., whereby the desired compound can be produced.
Next, typical phthalamide derivatives of the general formula (I) are exemplified in Tables 1, 2 and 3. The present invention is by no means limited by these examples. General formula (I)




































































The agrohorticultural insecticides containing the phthalamide derivative of the general formula (I) or salt thereof of the present invention as an active ingredient are suitable for controlling various insect pests such as agricultural insect pests, forest insect pests, horti¬cultural 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 fAdoxophyes orana fasciata), smaller tea tortrix fAdoxophyes sp.), Manchurian fruit moth fGrapholita inopinatal. oriental fruit moth fGrapholita molestal, soybean pod border (Leauminivora qlycinivorella), mulberry leafroller (Olethreutes mori), tea leafroller fCaloptilia thevivora). Caloptilia sp. fcalopilia zachrysal. apple leafminer f Phyllonorycter rinaoniellal, pear barkminer fSpulerrina astaurota^. common white fPiers rapae crucivora), tabacco budworm (Heliothis sp.) codling moth fLaspey resia pomonellal, diamondback moth fPlutella xylostella). apple fruit moth (Argyresthia coniuqellal, peach fruit moth (Carposina niponensis). rice stem borer (Chilo suppressalis), rice leafroller fCnaphalocrocis medinalis), tabacco moth fEphestia elutella), mulberry pyralid (Gj.yptiodQS pyloalis), yellow rice borer fScj-rpophaqa incertulas 1, rice skipper f Parnara guttata), rice armyworm f Pseudaletia separa-^a). pink borer (Sesamia infgrens), common cutworm (Spodop^era litura), beet armyworm fSpodoptera exiqua), etc; HEMIPTERA including aster leafhopper fMacrosteles fasqifrons), green rice leafhopper fWephotettix cincticeps), brown rice planthopper (Nilaparvata lugensi, whitebacked rice planthopper fSogatella fu£Cifera), citrus psylla fPiaphgrina citril. grape whitefly (Aleurolobus taonabae), sweetpotato whitefly fBemisia tabaci), greenhouse whitefly fTrialeurodes vaporarlorum^. turnip aphid (Lipaphis erysimi). green peach

aphid (Myzus persicaei, Indian wax scale (Ceroplastes ceriferus), cottony citrus scale (Pulvinaria aurantii), camphor scale (Pseudaonidia duplex). san Jose scale f Comstockaspis pernicicsa), arrowhead scale (Unaspis yanonensis\. etc.; TYLENCHIDA including root-lesion namatode fPratylenchus sp.), soybean beetle fAnomala rufocuprea), Japanese beetle fPopillia japonical. tabacco beetle ILasioderma serricorne'i. powderpost beetle (Lyctus brunneus). twenty-eight-spotted ladybird (Epilachna viaintiotopunctata1. azuki bean weevile (Callosobruchus chinensis), vegetable weevile (Listroderes costirostrisl. maize weevile (Sitophilus zeamaisl. boll weevile fAuthonomus gradis aradisl, rice water weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle (Aulacophora femoralis1. rice leaf beetle fOulema oryzael. striped flea beetle fPhyllotreta striolatal, pine shoot beetle fTomicus piniperdal. Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle (Epilachna varivestis), corn rootworm fPiabrotica sp.1, etc.; DIPTERA including melon fly fpacus(Zeugodacus) cugurbitae), oriental fruit fly {Pacus(Bactrocera) dorsalis\. rice leafminer (Agnomyza oryzae), onion maggot (Delia antigua), seedcorn maggot (Delia platura). soybean pod gall midge fAsphondylia sp.w muscid fly (Musea domestical. house mosquito (Culex pipiens pipiens1, etc.; and TYLENCHIDA including coffer root-lesion nematode (Pratylenchus coffeael, potato cyst nematode (Glotaodera rostocfaiensis1, root-knot nematode fMeloidogyne sp.), citrus nematode

fTvlenchulus semipenetrans1. Aphelenchus sp. (Aphelenchus avenae). chrysanthemum foliar fAphelenchoides ritzemabosi). etc.
The agricultural and horticultural insecticide containing the phthalamide derivative of the general formula (I) or salt thereof of the present invention as an active ingredient has a marked insecticidal effect on the above-exemplified insect pests, sanitary insect pests, and/or nematodes, which are injurious to paddy field crops, upland crops, fruit trees, vegetables, other crops, flowers and ornament plants, and the like. Therefore, the desired effect of the agricultural and horticultural insecticide of the present invention can be obtained by applying the insecticide to paddy field; upland field; crops such as fruits, vegetables, ornament plants and the like; seeds, flowers, stalks, leaves, etc. of plants itself; environ¬ments of plant growth such as paddy field water, soil, etc, at a season at which the insect pests, sanitary pests or nematodes are expected to appear, before their appearance or at the time when their appearance is confirmed.
In general, the agricultural and horticultural insecticide of the present invention is used after being prepared into conveniently usable forms according to an ordinary manner for preparation of agrochemicals.
That is, the phthalamide derivative of the general formula (I) or salt thereof and, optionally, an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable preparation

form such as a suspension, emulsifiable concentrate, soluble concentrate, wettable powder, granules, dust or tablets through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.
The inert carrier used in this invention may be either solid or liquid. 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 residues of vegetables, powdered synthetic polymers or resins, 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, i.e. 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), activated carbon, powdered sulfur, powdered pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic or mineral powders, 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 thereof.
The liquid carrier is that which itself has solubility or which is without such solubility but is 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 or as a mixture thereof, water; alcohols such as methanol, ethanol, isopropanol, butanol and ethylene glycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone and cyclohexanone; ethers such as ethyl ether, dioxane, Cellosolve, dipropyl ether and tetrahydro-furan; aliphatic hydrocarbons such as kerosene and mineral oils; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes; halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride and chlorobenzene; esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate; amides such as dimethylformamide, diethylformamide and dimethylacetamide; nitriles such as acetonitrile; and dimethyl sulfoxide.
The following are typical examples of the adjuvant, which are used depending upon purposes and used alone or in combination in some cases, or need not to be used at all.
To emulsify, disperse, dissolve and/or wet an 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 resinates, polyoxyethylene sorbitan mono-laurate, polyoxyethylene sorbitan monooleate, alkylarylsulfonates, naphthalene-sulfonic acid condensation products, ligninsulfonates and higher alcohol sulfate esters.

Further, to stabilize the dispersion of an active ingredient, tackify it and/or bind it, there may be used adjuvants such as casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose, gum^ arabic, polyvinyl alcohols, turpentine, bran oil, bentonite and ligninsulfo-nates.
To improve the flowabililty of a solid product, there may be used adjuvants such as waxes, stearates and alkyl phosphates.
Adjuvants such as naphthalenesulfonic acid condensation products and polycondensates of phosphates may be used as a peptiEer for dispersible products.
Adjuvants such as silicon oils may also be used as a defoaming agent.
The content of the active ingredient may be varied as required and may be chosen in a range of 0.01 to 80% by weight as an active ingredient. In dusts or granules, the suitable content thereof is from 0.01 to 50% by weight. In emulsifiable concentrates or flowable wettable powders, it is also from 0.01 to 50% by weight.
The agricultural and horticultural insecticide of the present invention is used to control a variety of insect pests in the following manner. That is, it is applied to a crop on which the insect pests are expected to appear or a site where the appearance of the insect pests is undesirable, as it is or after being properly diluted with or suspended inwater or the like, in an amount effec¬tive for control of the insect pests.

The applying dosage of the agricultural and horticultural insecticide 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 preparation form, an application method, an application site and an application time. It may be properly chosen in a range of 0.1 g to 10 kg (in terms of the active ingredient) per 10 ares depending upon purposes.
The agricultural and horticultural insecticide of the present invention may be used in admixture with other agricultural and horticultural disease or pest controllers, acaricides, nematicides, bioagrochemicals, etc.; and herbicides, plant growth regulators, manures, etc. depend¬ing upon scenes using the present agricultural and horti¬cultural insecticides, in order to expand both spectrum of controllable diseases and insect pest species and the period of time when effective applications are possible or to reduce the dosage.
The agrohorticultural insecticide of the present invention may be applied to the plant seeds or the cultiva¬tion mediums for seeding such as soil to be seeded, the mat for raising seedlings, water, etc. by the method of application to rice nursery box, seed powdering, etc. or by the method of seed disinfection. For controlling the pest insects generated on fruit trees, cereals, upland field for vegetables, etc., it is also possible to make a plant absorb the agrohorticultural agent of the present invention

by a seed treatment such as powder coating, dipping, etc., irrigation into seedling-raising carrier such as seedling-raising vessel, planting hole, etc. or by treatment of the culture solution for water culture.
EXAMPLES
Hext, typical examples of the present invention are presented below. The present invention is by no means limited by these examples.
Example 1
(1-1) Production of N-[4-(l,1,2,3,3,3-hexafluoropropoxy)-!-
methylphenyl]-3-nitrophthalimide
In 3 0 ml of acetic acid were dissolved 1.93 g of 3-nitrophthalic anhydride and 2.73 g of 4-(1,1,2,3,3,3-hexafLuoroprQpoxy)-l-methylaniline. A reaction was carried out for 3 hours with heating under reflux. After comple¬tion of the reaction, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane, whereby 4.4 g of the objective compound was obtained.
Property: m.p. 121°C; Yield: 98%
(1-2) Production of N^-[4-{ 1,1,2 ,3,3,3-hexafluoropropoxy)-l-methylphenyll-N^-(l-methyl-2-methylthioethyl)-3-nitrQ-phthalamide (Compound No. 223)
In 10 ml of dioxane was dissolved 0.54 g of N-[4-
{1,1,2,3,3,3-hexafluoropropoxy)-1-methylphenyl]-3-nitro-phthalimide. Then, 0.25 g of l-methyl-2-methylthioethyl-

amine and 0.01 g of acetic acid were added to the solution obtained above, and a reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by column chromato¬graphy using 1/1 mixture of hexane and ethyl acetate as an eluent. Thus, 0.45 g of the objective compound having an Rf value of 0,4 to 0.5 was obtained.
Property: m,p. 218°C; Yield: 68%
Example 2
(2-1) Production of 3-fluoro-N-(4-heptafluoroisopropyl-2-
methylphenyl)phthalimide
In 10 ml of acetic acid were dissolved 1.33 g of 3-fluorophthalic anhydride and 4-heptafluoroisopropyl-2-methylaniline. A reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane to obtain 3.1 g of the objective compound.
Property; m.p. 155-157°C; Yield: 97% (2-2) production of N-(heptafluoroisopropyl-2-methyl-phenyl)phthalimide
In 20 ml of dimethylformamide was dissolved 2.54 g of 3-fluoro-N-(4-heptafluoroisopropyl-2-methylphenyl)-phthalimide. After adding 2.8 g of a 15% aqueous solution of methylmercaptan to the solution obtained above, a reaction was carried out at room temperature for 3 hours

with stirring. After completion of the reaction, the reaction solution was poured into water, and the objective product was extracted with ethyl acetate. The extract solution was dried on anhydrous magnesium, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 2.2 g of the objective compound was obtained.
Property: m.p. 163-165°C; Yield: 81% (2-3) Production of N-(4-heptafluoroisopropyl-2-methyl-phenyl) -3-inethylsulf onylphthalimide
In 2 0 ml of dichloromethane was dissolved 0.63 g of N-{4-heptafluoroisopropyl-2-methylphenyl)-3-methylthio-phthalimide. While cooling the solution with ice, 0.58 g of m-chloroperbenzoic acid was added and reacted at room temperature. After completion of the reaction, the reaction solution was poured into water, and the objective product was extracted with chloroform. The organic layer was washed with an aqueous solution of sodium thiosulfate and an aqueous solution of potassium carbonate and dried on anhydrous magnesium, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 0.63 g of the objective compound was obtained.
Property: m.p. 185-187°C; Yield: 93% (2-4) Production of H^-(4-heptafluoroisopropyl-2-methyl-phenyl) -N=-(l-methyl-2-methylthioethyl)-3-methylsulfonyl-phthalamide (Compound No. 191) and N^-(4-heptafluoro-isopropyl-2-methylphenyl)-N'-(l-methyl-2-methylthioethyl)-6-

methylsulfonylphthalamide (Compound No. 192)
In 10 ml of dioxane was dissolved 0.63 g of N-(4-heptafluoroisopropyl-2-methylphenyl)-3-methylsulfonyl-phthalimide. After adding 0.25 g of l-methyl-2-metnylthioethylamine and 0.01 g of acetic acid to the solution obtained above, a reaction was carried out for 3 hours with heating under reflux. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography using 1/1 mixture of hexane and ethyl acetate as an eluent. Thus, 0.42 g of the first objective compound having an Rf value of 0.5 to 0.7 (Compound No. 191) and 0.18 g of the second objective compound having an Rf value of 0.2 to 0.3 (Compound No. 192) were obtained.
Compound No. 191: Property: m.p. 205-206°C;
Yield: 55%
Compound No. 192: Property: m.p. 210-212°C;
Yield: 24%
Example 3
(3-1) Production of 3-iodo-H-(l-methyl-3-methylthiopropyl)-
phthalamic acid
To a suspension of 2.74 g of 3-iodophthalic anhydride in 8 ml of acetonitrile cooled with ice was slowly added dropwise a solution of 1.19 g of l-methyl-3-methylthiopropylamine in 3 ml of acetonitrile. After completion of the dropping, a reaction was carried out at room temperature for 3 hours with stirring. After comple-

tion of the reaction, the deposited crystal was collected by filtration and washed with a small quantity of acetonitrile. Thus, 3.5 g of the objective compound was obtained.
Property: m.p. 148-150°C; Yield: 89% (3-2) Production of 6-iodo-N-(l-methyl-3-methylthiopropyl)-phthalisoimide
To a suspension of 0.79 g of 3-iodo-N-(1-methyl-3-methylthiopropyL)phthalamic acid in 10 ml of toluene was added 0.63 g of trifluoroacetic anhydride. A reaction was carried out at room temperature for 30 minutes with stirring. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 0.75 g of a crude objective product, which was used in the subsequent reaction without purification. (3-3) Production of 6-iodo-N'-(4-heptafluoroisopropyl-2-methylphenyl) -N^- (l-methyl-3-methylthiopropyl )phthalamide {Compound Ho, 162)
In 10 ml of acetonitrile was dissolved 0.75 g of 6-iodo-N-(l-methyl-3-methylthiopropyl)phthalisoimide. After adding 0.55 g of 4-heptafluoroisopropyl-2-methyl-aniline and 0.01 g of trifluoroacetic acid to the solution obtained above, a reaction was carried out for 3 hours with stirring. After completion of the reaction, the deposited crystal was collected by filtration and washed with a small quantity of cold acetonitrile. Thus, 1.17 g of the objec¬tive compound was obtained.
Property: m.p. 192-194°C; Yield: 90%

(3-4) Production of 3-iodo-N^-(4-heptafluoroisopropyl-2-methylphenyl) -N^- (l-methyl-3-methylsulf enylpropyl) -phthalamide (Compound No. 195)
In 10 ml of dichloromethane was dissolved 0.65 g of 6-iodo-N^- (4-heptafluoroisopropyl-2-methylphenyl) -N^-( 1-methyl-3-methylthiopropyl)phthalamide. After adding 0.18 g of m-chloroperbenzoic acid to the solution obtained above, a reaction was carried out at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into water, and the objective product was extracted with chloroform. The organic layer was washed with an aqueous solution of sodium thiosulfate and an aqueous solution of potassium carbonate and dried on anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 0.61 g of the objective compound was obtained.
property: m.p. 123-125°C; Yield: 92% (3-5) Production of 3-iodo-N'-(4-heptafluoroisopropyl-2-methylphenyl)-N^-{l-methyl-3-methylsulfonylpropyl)-
phthalamide (Compound Ho. 196)
3-Iodo-N^-( 4-heptaf luoroisopropyl-2-methylphenyl)-N=-(l-methyl-3-methylsulfenylpropyl)phthalamide (0.4 g) was treated in the same manner as in Example (3-4). Thus, 0.39 g of the objective compound was obtained.
Property: m.p. 128-130°C; Yield: 95%

Example 4
(4-1) Production of N-(4-heptafluoroisopropyl-2-methyl-phenyl)-3-trifluoromethoxybenzamide
In 50 ml of tetrahydrofuran was dissolved 2.24 g of 3-trifluoromethoxyben2oyl chloride, to which were slowly added dropwise 2.75 g of 4-heptafluoroisopropyl-2-methyl-aniline and 1.2 g of triethylamine. After completion of the dropping, a reaction was carried out at room tempera¬ture for 1 hour. After completion of the reaction, the reaction solution was poured into water, the objective product was extracted with ethyl acetate and dried on anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 4.6 g of the objective compound was obtained.
Property: Oily product; yield; 99% (4-2) Production of N-(4-heptafluoroisopropyl-2-methyl-phenyl)-3-trifluoromethoxyphthalamic acid
In 20 ml of tetrahydrofuran was dissolved 2.2 g of N-(4-heptafluoroisopropyl-2-methylphenyl)-3-trifluoro¬methoxybenzamide. At -70°C, 10 ml of s-butyllithium (0.96 M/L) was slowly added to the above solution and reacted at that temperature for 30 minutes. Then, the cooling bath was removed, and an excessive amount of carbon dioxide was introduced into the reaction, solution and reacted at room temperature for 3 0 minutes. After completion of the reaction, the reaction solution was poured into water and acidified with dilute hydrochloric acid, the objective

product was extracted with ethyl acetate and dried on anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was washed with a mixture of ether and hexane. Thus, 2.1 g of the objective compound was obtained.
Property: m.p. 168-172°C; Yield: 87% (4-3) Production of N-(4-heptafluoroisopropyl-2-methyl-phenyl)-3-trifluoromethoxyphthalisoimide
To a suspension of 0.46 g of N-(4-heptafluoro-isopropyl-2-methylphenyl)-3-trifluoromethoxyphthalamic acid in 10 ml of toluene was added 0.51 g of trifluoroacetic anhydride, and a reaction was carried out at room tempera¬ture for 30 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 0.49 g of a crude objective product. The product thus obtained was used in the subsequent reaction without purification.
(4-4) Production of N^-(4-heptafluoroisopropyl-2-methyl-phenyl )-B'-3-(l-methyl-2-methylthioethyl)-3-trifluoro-methoxyphthalamide (Compound No. 210)
In 10 ml of acetonitrile was dissolved 0.44 g of N-(4-heptafluoroisopropyl-2-methylphenyl)-3-trifluoro-methoxyphthalisoiOLide. Then, 0.10 g of l-methyl-2-raethyl-thioethylaniline and 0.01 g of trifluoroacetic acid were added to the solution obtained above, and reacted for 3 hours. After completion of the reaction, the reaction solution was cooled to 0°C, the deposited crystal was collected by filtration, and washed with hexane. Thus,

0.46 g of the objective compound was obtained. Property: m.p. 184-185°C; Yield: 77% Next, typical formulation examples of the present
invention and test examples are presented below. The
present invention is by no means limited by these examples. In the formulation examples, the term "parts"
means "parts by weight".
Formulation Example 1
Each compound listed in Table 1, 2 or 3 50 parts
Xylene 40 parts
Mixture of polyoxyethylene nonylphenyl 10 parts ether and calcium alkylbenzenesulfonate
An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolu¬tion.
Formulation Example 2
Each compound listed in Table 1, 2 or 3 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 Table 1, 2 or 3 5 parts
Mixed powder of bentonite and clay 90 parts
Calcium lignin sulfonate 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, 2 or 3 20 parts
Mixture of kaolin and synthetic 75 parts
high-dispersion silicic acid
Mixture of polyoxyethylene nonylphenyl 5 parts
ether and calcium alkylbenzenesulfonate
A wettable powder was prepared by mixing uniformly and grinding the above ingredients.
Test Example 1: Insecticidal effect on diamond back moth (Plutella xylostellal
Adult diamondback moths were released and allowed to oviposit on a Chinese cabbage seedling. Two days after the release, the seedling having the eggs deposited thereon was immersed for about 30 seconds in a liguid chemical prepared by diluting a preparation containing each compound listed in Table 1, 2 or 3 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, it was allowed to stand in a room thermostatted at 25°C* Six days after the immersion, the hatched insects were counted. The nortality was calculated according to the following sguation and the insecticidal effect was judged according to the criterion shown below. The test was carried out


A piece of cabbage leaf {cultivar; Shikidori) was immersed for about 30 seconds in a liquid chemical prepared oy diluting a preparation containing each compound listed Ln Table 1, 2 or 3 as an active ingredient to adjust the concentration to 50 ppm. After air-dryness, it was placed Ln a plastic Petri dish with a diameter of 9 cm and Inoculated with second-instar larvae of common cutworm, ifter which the dish was closed and then allowed to stand .n a room thermostatted at 25°C. Eight days after the .noculation, the dead and alive were counted. The mortality was calculated according to the following equation and the insecticidal effect was judged according

























h_^^ -^ I






















WE CLAIM :
1. A phthalamide derivative represented by the following general formula (!) or salt thereof.



alternatively, R may be combined with A' or R to form a 5- to 7-membered ring which may be intercepted by 1 or 2 same or different oxygen atoms, sulfur atoms or nitrogen atoms;

X which may be same or ditTerenl, represents
halogen atom; nitro group; C1-C6 alkyl group; halo C1-C6 alkyl group; C2-C6 alkenyl group; halo C1-C6 alkenyl group; C1-C6, alkynyl group; halo C2-C6 alkynyl group; C3-C5 cycloalkyl group: halo C3-C6 cycloalkyl group; C1-C6 alkoxy group; halo C1-C5 alkoxy group; C1-C6 alkylthio group; halo C1-C6 alkylthio group; C1-C6 atkylsulfmyl group; halo C1-C6 alkylsulfinyl group; Cp C(, alkylsulfonyl group: or halo C1-C6 alkylsulfonyl group; and



m represents an Integer of 1 to .5; and
Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one same or different substituents selected from the group consisting of halogen atom, C|-C6, alkyl

group, halo , alkoxy group, C\-Cf, alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthC1-C6io group, haloC1-C6 alkylthio group,C1-C6 alkylsulfinyl group; halo C1-C6 alkylsulfinyl group,C1-C6 alkylsulfonyl group and halo C1-C6, alkylsulfonyl group: and


I represents an integer of 1 to 2 and
alternatively, X may be taken conjoindy with the adjacent carbon atom on the phenyl ring to form a fused ring, and said fiised ring may have at least one, same or dC1-C6erent substituents selected from the group consisting of halogen atom, C1-C6ialkyl group, halo C1-C6alkyl group, C1-C6alkoxy group, halo C|-Ca alkoxy group; C1-C6 alkylthio group halo C1-C6 alkylthio group, C1-C6 alkylsulfmyl group, halo C1-C6 alkylsulfinyl group C1-C6alkylsulfonyl group and haloCi-C^alkylsulfonyl group.
Y may be same or different and represents
halogen atom; C1-C6 alkyl group; halo C1-C6 alkyl group; C1-C6, alkoxy halo C1-C6 alkyl group: C1-C6 alkoxy group; halo C1-C6 alkoxy group, halo C1-C6 alkoxy halo C1-C6 alkoxy group; C1-C6 alkylthio group; halo C1-C6, alkylthio group; C|1C6 alkylsulfmyl group; halC1-C6 alkylsulfinyl group: C1-C6, alkylsiilfony] group; halo €[-€,;, alkylsulfonyJ group; substituted phenyl group having at least one, same or different substituents selected from the group consisting of halogen atom C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group; halo C1-C6 alkoxy group; C1-C6alkylthio group, halo C1-C6 alkylthio group, haloC1-C6 alkylsulfmyl group and halo C1-C6 . alkylsulfonyl group: substituted phenoxy group having at least one, same or different substituents selected from the group consisting of halogen atom, C1-C6 alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6 alkylthio group, haloC1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group; or substituted pyridyloxy group having at least one, same or ditTerent substituents selected from the group consisting of halogen atom; C1-C6alkyl group, halo C1-C6 alkyl group, C1-C6 alkoxy group, halo C1-C6 alkoxy group, C1-C6alkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfinyl group and halo C1-C6 alkylsulfonyl group; and

m represents on integer 1 to 3 and
Y may be taken conjointly with an adjacent carbon atom on the phenyl ring to form a fused ring, and said fused ring may have at least one, same or different substituents selected from the group consisting of halogen atom C1-C6 alkyl group: halo C1-C6 alkyl group, C1-C6 alkoxy group; halo C1-C6 alkoxy group, aC1-C6lkylthio group, halo C1-C6 alkylthio group, halo C1-C6 alkylsulfmyl group and halo C1-C6alkylsulfonyl group; and
3

Documents:

1126-1999.rtf

1126-mas-1999 abstract duplicate.pdf

1126-mas-1999 abstract.pdf

1126-mas-1999 claims duplicate-1.pdf

1126-mas-1999 claims duplicate.pdf

1126-mas-1999 claims.pdf

1126-mas-1999 correspondence others.pdf

1126-mas-1999 correspondence po.pdf

1126-mas-1999 description (complete) duplicate-1.pdf

1126-mas-1999 description (complete) duplicate.pdf

1126-mas-1999 description (complete)-1.pdf

1126-mas-1999 description (complete).pdf

1126-mas-1999 form-1.pdf

1126-mas-1999 form-18.pdf

1126-mas-1999 form-26.pdf

1126-mas-1999 form-3.pdf

1126-mas-1999 form-5.pdf

1126-mas-1999 others-1.pdf

1126-mas-1999 others-2.pdf

1126-mas-1999 others-3.pdf

1126-mas-1999 others.pdf

1126-mas-1999 petition.pdf


Patent Number 225112
Indian Patent Application Number 1126/MAS/1999
PG Journal Number 52/2008
Publication Date 26-Dec-2008
Grant Date 30-Oct-2008
Date of Filing 17-Nov-1999
Name of Patentee NIHON NOHYAKU CO., LTD
Applicant Address 1-2-5, NOHONBASHI, CHUO-KU, TOKYO
Inventors:
# Inventor's Name Inventor's Address
1 SHINSUKE FUJIOKA 1-28, NISHINOYAMACHO, KAWACHINAGANO-SHI,
2 HIDEO KANNO 2-2-708, SHIRAKAWA-3-CHOME, IBARAKI-SHI,
3 MASANORI TOHNISHI 296-1-201, KITANODA, SAKAI-SHI
4 HAYAMI NAKAO 473-6-902, KIDOCHO, KAWACHINAGANO-SHI,
5 EIJI HOHNO 756-2, KONDA-7-CHOME, HABIKINO-SHI,
6 TATAKI NISHIDA 7-22-202, KODA-3-CHOME, TONDABAYASHI-SHI,
7 TAKASHI FURUYA 2821, NINENO, IZUMISANO-SHI,
8 TOSHIAKI SHIMIZU 974-90-303, KIDOCHO, KAWACHINAGANO-SHI,
9 AKIRA SEO 3-19, KIMIGAOKA-2-CHOME, HASHIMOTO-SHI,
10 KAZUYUKI SAKATA 5-6-301, HONDACHO, KAWACHINGANO-SHI,
PCT International Classification Number A01N 43/10
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 10-340379 1998-11-30 Japan
2 11-234329 1999-08-20 Japan