Title of Invention

BENZOYLPYRAZOLE COMPOUNDS AND HERBICIDES CONTAINING THEM

Abstract A benzoylpyrazole compound represented by the formula (I) or its salt: wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom or alkyl, R3 is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl which may be substituted by R8, R4 is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R5 is a hydrogen atom; alkyl; alkenyl; alkynyl; halogen; cyano; cyanoalkyl; cyanoalkeny; haloalkyl; alkoxyalkyl; haloalkoxyalkyl; amino (thiocarbonyl) alkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl (thiocarbonyl)alkyl, -C(O)OR7 and -C(O)SR7; thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy; haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy; alkoxyhaloalkoxy; haloalkoxyhaloalkoxy; alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio; haloalkoxyalkylthio; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio; alkylthioalkylthio; haloalkylthioalkylthio; alkylthiohaloalkylthio; haloalkylthiohaloalkylthio; alkylthioalkoxy; alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl; alkoxycarbonylalkoxy; heterocyclylalkyl; heterocyclyloxy; heterocyclylalkoxy; heterocyclylalkoxyalkyl; heterocyclyloxyalkyl; cycloalkyloxy; -OC(O)SR7; -OC(O)OR7; -C(O)OR7; -C(O)SR7; -C(S)OR7; -C(S)SR7; aminoalkyl which may be substituted by at least one substituent selected from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, -C(O)OR7 and -C(O)SR7; or 4,5-dihydroisoxazol-3-yl which may be substituted by R9, R6 is haloalkyl; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R7 is alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl which may be substituted by R10, and each of R8, R9 and R10 which are independent of one another, is halogen; alkyl; or alkoxy.
Full Text DESCRIPTION
BENZOYLPYRAZOLE COMPOUNDS AND HERBICIDES CONTAINING THEM
TECHNICAL FIELD
The present invention relates to novel
benzoylpyrazole compounds useful as an active ingredient
of herbicides.
BACKGROUND ART
WO96/26206, JP-A-50-126830, JP-A-2-288866 and JP-A-
2-173 disclose benzoylpyrazole compounds. However, they
differ from benzoylpyrazole compounds represented by the
following formula (I) in the chemical structure.
DISCLOSURE OF THE INVENTION
OBJECT TO BE ACCOMPLISHED BY THE INVENTION
Heretofore, herbicides which have excellent
herbicidal activity against weeds and which are safe for
crop plants, have been desired for labor saving in the
operation of controlling weeds and for improvement of
productivity of agricultural and horticultural plants.
However, search for novel compounds suitable for such an
object depends on trial and error.
MEANS TO ACCOMPLISH THE OBJECT
The present inventors have conducted extensive

studies on benzoylpyrazole compounds in order to find
more excellent herbicides which accomplish the above
object and as a result, accomplished the present
invention.
Namely, the present invention relates to a
benzoylpyrazole compound represented by the formula (I)
or its salt:

wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom
or alkyl, R3 is alkyl; cycloalkyl; haloalkyl;
alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl
which may be substituted by R8, R4 is alkyl; haloalkyl;
alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl;
or alkylsulfonyl, R5 is a hydrogen atom; alkyl; alkenyl;
alkynyl; halogen; cyano; cyanoalkyl; cyanoalkenyl;
haloalkyl; alkoxyalkyl; haloalkoxyalkyl;
amino (thiocarbonyl)alkyl which may be substituted by at
least one substituent selected from alkyl, cyano,
cyanoalkyl, (alkylthio)carbonylalkyl,
alkyl (thiocarbonyl)alkyl, -C(O)OR7 and -C(O)SR7;
thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy;

haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy;
alkoxyhaloalkoxy; haloalkoxyhaloalkoxy;
alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio;
haloalkoxyalkylthio; alkoxyhaloalkylthio;
haloalkoxyhaloalkylthio; alkylthioalkylthio;
haloalkylthioalkylthio; alkylthiohaloalkylthio;
haloalkylthiohaloalkylthio; alkylthioalkoxy;
alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl;
alkoxycarbonylalkoxy; heterocyclylalkyl; heterocyclyloxy;
heterocyclylalkoxy; heterocyclylalkoxyalkyl;
heterocyclyloxyalkyl; cycloalkyloxy; -OC(O)SR7;
-OC(O)OR7; -C(0)0R7; -C(0)SR7; -C(S)OR7; -C(S)SR7;
aminoalkyl which may be substituted by at least one
substituent selected from alkyl, cyano, cyanoalkyl,
(alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl,
-C(O)OR7 and -C(O)SR7; or 4,5-dihydroisoxazol-3-yl which
may be substituted by R9, R6 is haloalkyl; halogen;
nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl,
R7 is alkyl; haloalkyl; alkoxyalkyl; alkenyl;
haloalkenyl; alkynyl; or arylalkyl which may be
substituted by R10, and each of R8, R9 and R10 which are
independent of one another, is halogen; alkyl; or alkoxy,
a process for producing it, a herbicide containing it as
an active ingredient, and a method for controlling
undesired plants or inhibiting their growth, which
comprises applying a herbicidally effective amount of it
to the undesired plants or to a place where they grow.

The compounds represented by the formula (I) have
excellent herbicidal effects.
BEST MODE FOR CARRYING OUT THE INVENTION
The alkyl or alkyl moiety in each of R1, R2, R3, R4,
R5, R6, R7, R8, R9 and R10 may be linear or branched, and
specific examples thereof include C1-9 alkyl such as
methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl,
sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl,
tert-pentyl, n-hexyl, iso-hexyl, n-heptyl, n-octyl and n-
nonyl.
Examples of the cycloalkyl or cycloalkyl moiety in
each of R1, R3 and R5 include C3-6 cycloalkyl such as
cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
The alkenyl or alkenyl moiety in each of R3, R5 and
R7 may be linear or branched, and specific examples
thereof include C2-9 alkenyl such as vinyl, 1-propenyl, 2-
propenyl, iso-propenyl, allyl, 1-butenyl, 2-butenyl, 3-
butenyl, 1,3-butadienyl, 2-pentenyl, 4-pentenyl, 2-
hexenyl, 4-hexenyl, 2-heptenyl, 4-heptenyl, 2-octenyl, 6-
octenyl and 2-nonenyl.
The alkynyl or alkynyl moiety in each of R5 and R7
may be linear or branched, and specific examples thereof
include C2-9 alkynyl such as ethynyl, propargyl, 1-
propynyl, 1-pentynyl, 3-pentynyl, 1-heptynyl and 1-
nonynyl.
Examples of halogen or halogen as the substituent in

each of R3, R4, R5, R6, R7, R8, R9 and R10 include atoms of
fluorine, chlorine, bromine and iodine.
The number of halogens as substituents in each of R3,
R4, R5, R6 and R7 may be 1 or more, and if more, they may
be the same or different. Further, the positions for
substitution of such halogens may be any positions.
The number of alkoxy or alkoxy moieties as
substituents in each of R3, R5 and R7 may be 1 or more,
and if more, they may be the same or different. Further,
the positions for substitution may be any positions.
Examples of the aryl or aryl moiety as the
substituent in each of R3 and R7 include phenyl and
naphthyl. The number of aryl or aryl moieties as
substituents may be 1 or more, and if more, they may be
the same or different. Further, the positions for
substitution may be any positions.
The number of R8 as substituents which substitute the
arylalkyl in R3 may be 1 or more, and if more, they may
be the same or different. Further, the positions for
substitution of such substituents may be any positions.
The number of R10 as substituents which substitute
the arylalkyl in R7 may be 1 or more, and if more, they
may be the same or different. Further, the positions for
substitution of such substituents may be any positions.
The number of R9 as substituents which substitute the
4,5-dihydroisoxazol-3-yl in R5 may be 1 or more, and if
more, they may be the same or different. Further, the

positions for substitution of such substituents may be
any positions.
The alkoxyalkoxy in R5 is meant for an alkoxy group
having the same or different alkoxy moiety bonded thereto.
The position for substitution of the alkoxy moiety which
substitutes the alkoxy group may be any position. The
same applies to haloalkoxyalkoxy, alkoxyhaloalkoxy,
alkoxyalkoxyalkyl, alkylthioalkylthio, alkylsulfonylalkyl,
alkoxycarbonylalkyl, etc.
The heterocyclyl moiety in R5 may, for example, be a
saturated or unsaturated 5-membered or 6-membered ring
containing 1 to 4 one or more types of hetero atoms
optionally selected from O, S and N, and specific
examples thereof include oxolanyl, 1,3-dioxolanyl,
tetrahydrofuranyl and tetrahydro-2H-pyranyl. Further,
the number of heterocyclyl moieties as substituents may
be 1 or more, and if more, they may be the same or
different. The positions for substitution of the
heterocyclyl moieties may be any positions.
The salt of the benzoylpyrazole compound represented
by the above formula (I) includes all kinds of salts so
long as they are agriculturally acceptable. Examples
thereof include alkali metal salts such as a sodium salt
and a potassium salt; alkaline earth metal salts such as
a magnesium salt and a calcium salt; amine salts such as
a dimethylatnine salt and a triethylamine salt; inorganic
acid salts such as a hydrochloride, a perchlorate, a

sulfate and a nitrate; and organic acid salts such as an
acetate and a methanesulfonate.
The benzoylpyrazole compound represented by the
above formula (I) or its salt (hereinafter referred to
simply as the compound of the present invention) can be
produced by the following reactions [A] to [AG] and in
accordance with a usual method for producing a salt.
The compound of the present invention represented by
the above formula (I) can be produced in accordance with
the following reaction [A].

wherein R1, R2, R3, R4, R5 and R6 are as defined above, and
Z is a leaving group such as halogen.
Namely, the compound of the present invention
represented by the above formula (I) can be produced by
reacting a compound represented by the formula (II) with
a compound represented by the formula (III) .
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and

trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either inorganic base or organic base. Examples of
the inorganic base include alkali metal hydrides such as
sodium hydride and potassium hydride; alkali metal
hydroxides such as sodium hydroxide and potassium
hydroxide; alkali metal carbonates such as sodium
carbonate and potassium carbonate; alkali metal
hydrogencarbonates such as sodium hydrogencarbonate and
potassium hydrogencarbonate; alkaline earth metal
hydroxides such as calcium hydroxide; and alkaline earth
metal carbonates such as calcium carbonate. Examples of
the organic base include tertiary amines such as
triethylamine and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. As the base,
one or more types may suitably be selected and mixed.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The above reaction may also be carried out in the

two-phase system in water and a solvent insoluble in
water among the above solvents in the presence of a phase
transfer catalyst such as a quaternary ammonium salt.
As mentioned above, compounds represented by the
above formula (II) are useful as an intermediate for
preparation of the compounds represented by the formula
(I) . Further, some of the compounds represented by the
formula (II) are novel, which are exemplified below.
Benzoylpyrazole compounds represented by the formula
(II-x) or their salts:

wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom
or alkyl, R4 is alkyl; haloalkyl; alkoxy; halogen; nitro;
cyano; alkylthio; alkylsulfinyl, or alkylsulf onyl, R5-X is
alkyl substituted by at least 2 alkoxy; alkyl substituted
by at least 2 haloalkoxy; amino(thiocarbonyl)alkyl which
may be substituted by at least one substituent selected
from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl,
alkyl (thiocarbonyl) alkyl, -C(O)OR7 and -C(O)SR7;
thiocyanatoalkyl; alkoxy substituted by at least 2 alkoxy,
alkoxy substituted by at least 2 haloalkoxy;
alkoxyhaloalkoxy; haloalkoxyhaloalkoxy; alkoxyalkyl
substituted by at least 2 alkoxy; alkylthio substituted

by at least 2 alkoxy; alkylthio substituted by at least 2
haloalkoxy; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio;
alkylthioalkylthio; haloalkylthioalkylthio;
alkylthiohaloalkylthio; haloalkylthiohaloalkylthio;
alkylthioalkoxy; alkyl substituted by at least 2
alkylsulfonyl; alkyl substituted by at least 2
alkoxycarbonyl; alkoxy substituted by at least 2
alkoxycarbonyl; alkyl substituted by at least 2
heterocyclyl; alkoxy substituted by at least 2
heterocyclyl; alkyl substituted by at least 2
heterocyclylalkoxy; -OC(O)SR7; or aminoalkyl which may be
substituted by at least one substituent selected from
cyano, cyanoalkyl, (alkylthio)carbonylalkyl,
alkyl (thiocarbonyl) alkyl, -C(O)OR7 and -C(O)SR7, R6 is
haloalkyl; halogen; nitro; cyano; alkylthio;
alkylsulfinyl; or alkylsulfonyl, R7 is alkyl; haloalkyl;
alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl
which may be substituted by R10, and R10 is halogen;
alkyl; or alkoxy.
In addition, among the compounds of the present
invention represented by the above formula (I), a
compound wherein R3 is R3-a can be produced in accordance
with the following reaction [B-l].


wherein R1, R2, R4, R5 and R6 are as defined above, R3-a is
alkyl; cycloalkyl; haloalkyl; alkoxyalkyl;
alkoxycarbonylalkyl; alkenyl; or arylalkyl which may be
substituted by R8.
Namely, the compound of the present invention
represented by the above formula (I-a) can be produced by
reacting a compound represented by the formula (IV-a) or
the formula (V-a) with a compound represented by the
formula (VI-a), or by reacting a mixture of a compound
represented by the formula (IV-a) and a compound
represented by the formula (V-a) with a compound
represented by the formula (VI-a).
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl

ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either inorganic base or organic base. Examples of
the inorganic base include alkali metal hydrides such as
sodium hydride and potassium hydride; alkali metal
hydroxides such as sodium hydroxide and potassium
hydroxide; alkali metal carbonates such as sodium
carbonate and potassium carbonate; alkali metal
hydrogencarbonates such as sodium hydrogencarbonate and
potassium hydrogencarbonate; alkaline earth metal
hydroxides such as calcium hydroxide; and alkaline earth
metal carbonates such as calcium carbonate. Examples of
the organic base include tertiary amines such as
triethylamine and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. As the base,
one or more types may suitably be selected and mixed.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds of the present invention
represented by the above formula (I), a compound wherein
R3 is R3-b can be produced in accordance with the
following reaction [B-2].


wherein R1, R2, R4, R5 and R6 are as defined above, and
R3-b is alkenyl.
Namely, the compound of the present invention
represented by the above formula (I-b) can be produced by
reacting a compound represented by the formula (IV-b) or
the formula (V-b) with a compound represented by the
formula (VI-b), or by reacting a mixture of a compound
represented by the formula (IV-b) and a compound
represented by the formula (V-b) with a compound
represented by the formula (VI-b).
The above reaction can be carried out in the
presence of a solvent, as the case requires. Examples of
the solvent include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.

The above reaction can be carried out in the
presence of a base, as the case requires. The base may-
be either inorganic base or organic base. Examples of
the inorganic base include alkali metal hydrides such as
sodium hydride and potassium hydride; alkali metal
hydroxides such as sodium hydroxide and potassium
hydroxide; alkali metal carbonates such as sodium
carbonate and potassium carbonate; alkali metal
hydrogencarbonates such as sodium hydrogencarbonate and
potassium hydrogencarbonate; alkaline earth metal
hydroxides such as calcium hydroxide; and alkaline earth
metal carbonates such as calcium carbonate. Examples of
the organic base include tertiary amines such as
triethylamine and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. As the base,
one or more types may suitably be selected and mixed.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The above compound represented by the formula (IV-a)
or the formula (V-a) or a mixture thereof can be produced
in accordance with the following reaction [C-l].


wherein R1, R2, R4, R5 and R6 are as defined above.
Namely, the compound represented by the formula (IV-
a) or the formula (V-a) or a mixture thereof can be
produced by reacting a compound represented by the
formula (II) with phosgene (COC12) .
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either inorganic base or organic base. Examples of
the inorganic base include alkali metal hydrides such as
sodium hydride and potassium hydride; alkali metal
hydroxides such as sodium hydroxide and potassium
hydroxide; alkali metal carbonates such as sodium
carbonate and potassium carbonate; alkali metal
hydrogencarbonates such as sodium hydrogencarbonate and
potassium hydrogencarbonate; alkaline earth metal

hydroxides such as calcium hydroxide; and alkaline earth
metal carbonates such as calcium carbonate. Examples of
the organic base include tertiary amines such as
triethylamine and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. As the base,
one or more types may suitably be selected and mixed.
The above reaction can be carried out at a reaction
temperature of usually from -10°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The above compound represented by the formula (IV-b)
or the formula (V-b) or a mixture thereof can be produced
in accordance with the following reaction [C-2].

wherein R1, R2, R4, R5 and R6 are as defined above.
Namely, the compound represented by the formula (IV-
b) or the formula (V-b) or a mixture thereof can be
produced by reacting a compound represented by the
formula (II) with thiocarbonyl chloride (CSC12) .
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and

trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either inorganic base or organic base. Examples of
the inorganic base include alkali metal hydrides such as
sodium hydride and potassium hydride; alkali metal
hydroxides such as sodium hydroxide and potassium
hydroxide; alkali metal carbonates such as sodium
carbonate and potassium carbonate; alkali metal
hydrogencarbonates such as sodium hydrogencarbonate and
potassium hydrogencarbonate; alkaline earth metal
hydroxides such as calcium hydroxide; and alkaline earth
metal carbonates such as calcium carbonate. Examples of
the organic base include tertiary amines such as
triethylamine and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. As the base,
one or more types may suitably be selected and mixed.
The above reaction can be carried out at a reaction
temperature of usually from -10°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds represented by the above formula

(II), some compounds are known compounds, such as a
compound wherein R4 is alkyl, R5 is alkoxyalkyl,
alkoxycarbonyl, alkoxyalkoxycarbonyl or
haloalkoxycarbonyl, and R6 is alkylsulfonyl, as disclosed
in European Patent Publication No. 0282944, at pages 36
to 41, a compound wherein R4 is halogen, R5 is
alkoxyalkoxy or heterocyclylalkoxy, and R6 is
alkylsulfonyl, as disclosed in European Patent
Publication No. 0352543, at pages 16 to 20, a compound
wherein R4 is halogen, R5 is alkoxyalkoxyalkyl or alkoxy,
and R6 is alkylsulfonyl, as disclosed in European Patent
Publication No. 0344775, at pages 25 o 27, and a compound
wherein R4 is halogen, R5 is 4,5-dihydroisoxazol-3-yl,
and R6 is halogen or alkylsulfonyl, as disclosed in
WO98/31681, at pages 121 to 127, and they can be produced
in accordance with a method disclosed in each publication
or a method similar thereto.
wherein R1, R2, R4, R5 and R6 are as defined above.
The compound represented by the above formula (II)
can be produced in accordance with the following reaction
[D] .


Namely, the compound represented by the formula (II)
can be produced by subjecting a compound represented by
the formula (VII) to rearrangement reaction.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either organic base or inorganic base. Examples of
the organic base include tertiary amines such as
triethylamine and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. Examples of
the inorganic base include alkali metal carbonates such
as sodium carbonate and potassium carbonate, alkali metal
hydroxides such as sodium hydroxide and potassium
hydroxide; and alkali metal cyanides such as sodium
cyanide and potassium cyanide. As the base, one or more
types may suitably be selected and mixed in an amount of

from 0.01 to 100 equivalent amounts based on the compound
of the formula (VII).
Further, for the above reaction, a catalyst may be
added as the case requires. As the catalyst, acetone
cyanohydrin can be used in an amount of from 0.01 to 10
equivalent amounts based on the compound of the formula
(VII).
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula (VII)
can be produced in accordance with the following reaction
[E] .

wherein R1, R2, R4, R5 and R6 are as defined above.
Namely, the compound represented by the formula
(VII) can be produced by reacting a compound represented
by the formula (VIII) or its salt, such as a
hydrochloride, a sulfate or a nitrate, with a compound
represented by the formula (IX).
The above reaction can be carried out in the

presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either inorganic base or organic base. Examples of
the organic base include tertiary amines such as

triethylamine and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. Examples of
the inorganic base include alkali metal carbonates such
as sodium carbonate and potassium carbonate; alkaline
earth metal carbonates such as calcium carbonate and
magnesium carbonate; alkali metal hydrogencarbonates such
as sodium hydrogencarbonate and potassium
hydrogencarbonate; and alkali metal hydroxides such as
sodium hydroxide and potassium hydroxide. As the base,
one or more types may suitably be selected and mixed in
an amount of from 1 to 10 0 equivalent amounts based on
the compound of the formula (IX) .

The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula (IX)
can be produced in accordance with the following reaction
[F] .

wherein R4, R5 and R6 are as defined above.
Namely, the compound represented by the formula (IX)
can be produced by reacting a compound represented by the
formula (X) with a halogenating agent. This reaction is
a method disclosed in literature (Organic Syntheses,
Collective Volume 4, page 715, Collective Volume 9, page
516, etc.) .
In the above reaction, a halogenating agent such as
thionyl chloride or oxalyl chloride is reacted in an
amount of from 1 to 100 equivalent amounts based on the
compound represented by the formula (X).
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and

trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
For the above reaction, a catalyst can be used, as
the case requires. The catalyst may, for example, be DMF.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
In addition to the above processes, the compound
represented by the formula (VII) can be produced in
accordance with the following reaction [G].

wherein R1, R2, R4, R5 and R6 are as defined above.
Namely, the compound represented by the formula
(VII) can be produced by reacting a compound represented
by the formula (VIII) or its salt, such as a
hydrochloride, a sulfate or a nitrate, with a compound

represented by the formula (X) by means of a dehydrating
agent.
The dehydrating agent to be used for the above
reaction may, for example, be DCC
(dicyclohexylcarbodiimide) or l-ethyl-3- (3 -
dimethylaminopropyl)-carbodiimide hydrochloride.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. Examples of
the base include tertiary amines such as triethylamine
and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2 , 6-lutidine. As the base,
one or more types may suitably be selected and mixed in
an amount of from 1 to 100 equivalent amounts based on
the compound represented by the formula (X).
The above reaction can be carried out at a reaction

temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds represented by the formula (X),
compounds wherein R4 is alkyl, R5 is haloalkoxy, and R6 is
alkylthio or alkylsulfonyl, are known compounds disclosed
in WO96/14285, pages 31 and 32, etc. They can be
produced in accordance with a method disclosed in the
publication, etc. or a method similar thereto.
The compound represented by the above formula (X)
can be produced in accordance with the following reaction
[H] .

wherein R4, R5 and R6 are as defined above, and L is a
protective group such as alkyl.
The compound represented by the formula (X) can be
produced by subjecting a compound represented by the
formula (XI) to hydrolysis.
The above reaction can be carried out in the
presence of a solvent, as the case requires. Examples
include aromatic hydrocarbons such as benzene, toluene
and xylene; aprotic polar solvents such as acetonitrile,
N,N-dimethylformamide, dimethylsulfoxide, sulfolane and

dimethoxyethane; ethers such as diethyl ether, dioxane
and tetrahydrofuran; alcohols such as methanol and
ethanol; and water. As the solvent, one or more types
may suitably be selected.
The above reaction can be carried out in the
presence of a base or an acid, as the case requires. The
base may be either inorganic base or organic base.
Examples of the inorganic base include alkali metal
hydroxides such as lithium hydroxide and sodium
hydroxide; alkali metal carbonates such as potassium
carbonate and sodium carbonate; and alkaline earth metal
carbonates such as calcium carbonate and barium carbonate.
Examples of the organic base include tertiary amines such
as triethylamine and diisopropylethylamine. Examples of
the acid include hydrochloric acid, sulfuric acid and
perchloric acid. As the base or acid, one or more types
may suitably be selected and mixed in an amount of from 1
to 10 0 equivalent amounts based on the compound
represented by the formula (XI).
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds represented by the above formula
(XI), a compound represented by the formula (XI-a-1)
wherein R5 is R5-a-1 can be produced in accordance with the
following reaction [I].


wherein R4, R6 and L are as defined above, R5-a-1 is alkoxy,
haloalkoxy, alkoxyalkoxy, haloalkoxyalkoxy,
alkoxyhaloalkoxy, haloalkoxyhaloalkoxy, heterocyclyloxy,
heterocyclylalkoxy, cycloalkyloxy, -OC(O)SR7, -OC(O)OR7,
alkylthioalkoxy, alkoxycarbonylalkoxy, alkenyloxy or
alkynyloxy and R is alkyl, haloalkyl, alkoxyalkyl,
haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl,
heterocyclyl, heterocyclylalkyl, cycloalkyl, -C(O)SR7,
-C(O)OR7, alkylthioalkyl, alkoxycarbonylalkyl, alkenyl or
alkynyl.
Namely, the compound represented by the formula (XI-
a-1) can be produced by reacting a compound represented
by the formula (XII) with a compound represented by the
formula (XIII) by means of a dehydrating agent.
The dehydrating agent to be used in the above
reaction may, for example, be DCC
(dicyclohexylcarbodiimide), l-ethyl-3-(3-
dimethylaminopropyl)-carbodiimide hydrochloride or
diethylazodicarboxylate.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.

Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. Examples of
the base include tertiary amines such as triethylamine
and diisopropylethylamine; pyridine, 4-
(dimethylamino)pyridine and 2 , 6-lutidine. As the base,
one or more types may suitably be selected and mixed in
an amount of from 1 to 10 0 equivalent amounts based on
the compound represented by the formula (XII).
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds represented by the above formula
(XII), compounds wherein R4 is alkyl, and R6 is alkylthio
or alkylsulfonyl, are known compounds disclosed in
WO97/35851, at pages 54 to 55, etc. They can be produced
in accordance with a method disclosed in the publication,
etc. or a method similar thereto.
In addition to the above processes, the compound

represented by the formula (XI-a-1) can also be produced
in accordance with the following reaction [J].

wherein R4, R5-a-1, R6, R and L are as defined above, and
X is a leaving group such as halogen or a
methanesulfonyloxy group.
Namely, the compound represented by the formula (XI-
a-1) can be produced by reacting a compound represented
by the formula (XII) with a compound represented by the
formula (XIV) in the presence of a base.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.

The base to be used in the above reaction may be
either inorganic base or organic base. Examples of the
organic base include triethylamine, diisopropylethylamine,
pyridine, 4 -(dimethylamino)pyridine and 2,6-lutidine.
Examples of the inorganic base include alkali metal
carbonates such as sodium carbonate and potassium
carbonate; alkali metal hydroxides such as sodium
hydroxide and potassium hydroxide; and alkali metal
hydrides such as sodium hydride and potassium hydride.
As the base, one or more may suitably be selected and
mixed in an amount of from 0.5 to 100 equivalent amounts
based on the compound of the formula (XII).
The above reaction can be carried out in the
presence of a catalyst, as the case requires. The
catalyst may, for example, be potassium iodide or tetra-
n-butylammonium iodide.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 4 8 hours.
The compound represented by the above formula (XII)
can be produced in accordance with the following reaction
[K] .


wherein R4, R6 and L are as defined above.
Namely, the compound represented by the formula
(XII) can be produced by reacting a compound represented
by the formula (XV) with a Lewis acid such as BBr3.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, and esters such as methyl acetate,
ethyl acetate and propyl acetate. As the solvent, one or
more types may suitably be selected.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
wherein R4, R6 and L are as defined above.
Namely, the compound represented by the formula (XV)
The compound represented by the above formula (XV)
can be produced in accordance with the following reaction
[L] .


can be produced by a reaction of introducing a protective
group L into a compound represented by the formula (XVI).
The above reaction can be carried out in the
presence of a solvent, as the case requires. Examples of
the solvent include alcohols such as methanol and
ethanol; aromatic hydrocarbons such as benzene, toluene
and xylene; esters such as methyl acetate, ethyl acetate
and propyl acetate; halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; and aprotic polar solvents such as
acetonitrile, N,N-dimethylformamide; dimethylsulfoxide,
sulfolane and dimethoxyethane. As the solvent, one or
more may suitably be selected.
The above reaction can be carried out in the
presence of an acid, as the case requires. Examples of
the acid to be used for the above reaction include
hydrochloric acid and sulfuric acid.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula (XVI)
can be produced in accordance with a known method. For
example, among the compounds represented by the formula
(XVI), a compound wherein R4 is alkyl, and R6 is
alkylsulfonyl, as disclosed in WO93/13 060, at page 4, and
a compound wherein R4 is halogen, and R6 is alkylsulfonyl,
as disclosed in JP-A-2-45448, at page 6, are known

compounds, and they can be produced in accordance with a
method disclosed in each publication or a method similar
thereto.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-2 can be produced in
accordance with the following reaction [M].

wherein R4, R6 and L are as defined above, and R5-a-2 is
alkylthiocarbonyl.
Namely, the compound represented by the formula (XI-
a-2) can be produced by reacting a compound represented
by the formula (XVIII) with alkylthiol.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reactior
Examples thereof include ethers such as diethyl ether,
dioxane and tetrahydrofuran; aromatic hydrocarbons such
as benzene, toluene and xylene; esters such as methyl
acetate, ethyl acetate and propyl acetate; and
halogenated hydrocarbons such as methylene chloride,
chloroform, dichloroethane and trichloroethane. As the
solvent, one or more types may suitably be selected.
The above reaction can be carried out in the

presence of a base, as the case requires. The base may-
be either inorganic base or organic base. Examples of
the organic base include triethylamine,
diisopropylethylamine, pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. Examples of
the inorganic base include alkali metal carbonates such
as potassium carbonate and sodium carbonate; alkali metal
hydroxides such as sodium hydroxide and potassium
hydroxide; and alkali metal hydrides such as sodium
hydride and potassium hydride. As the base, one or more
types may suitably be selected and mixed.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula
(XVIII) can be produced in accordance with the following
reaction [N].

wherein R4, R6 and L are as defined above.
Namely, the compound represented by the formula
(XVIII) can be produced by reacting a compound
represented by the formula (XIX) with a halogenating
agent. This reaction can be carried out in the same

manner as the above-described reaction [F]
The compound represented by the above formula (XIX)
can be produced in accordance with the following reaction
[o] .

wherein R4, R6 and L are as defined above.
Namely, the compound represented by the formula
(XIX) can be produced by oxidizing a compound represented
by the formula (XX).
The oxidizing agent in the above reaction may, for
example, be potassium permanganate or chromium trioxide.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include ketones such as acetone and
methyl ethyl ketone; esters such as methyl acetate, ethyl
acetate and propyl acetate; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula (XX)

can be produced in accordance with the following reaction
[P] .

wherein R4, R6 and L are as defined above.
Namely, the compound represented by the formula (XX)
can be produced by reacting a compound represented by the
formula (XXI) with an oxidizing agent in the presence of
a solvent.
The oxidizing agent to be used for the above
reaction may, for example, be N-methylmorpholine oxide.
The solvent to be used for the above reaction may be
any solvent so long as it is inert to the reaction.
Examples thereof include aprotic polar solvents such as
acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compounds represented by the above formula (XX)
and the formula (XXI) can be produced by known methods.

For example, among the compounds represented by the
formulae (XX) and (XXI), a compound wherein R4 is alkyl,
and R6 is alkylsulfonyl, as disclosed in JP-A-11-240872,
at page 9, and a compound wherein R4 is halogen, and R6
is alkylsulfonyl, as disclosed in WO98/29392, at page 264,
are known compounds, and they can be produced in
accordance with a method disclosed in each publication or
a method similar thereto.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-3 can be produced in
accordance with the following reaction [Q].

wherein R4, R6 and L are as defined above, and R5-a-3 is
alkylsulfonylalkyl.
Namely, the compound represented by the formula (XI-
a-3) can be produced by reacting a compound represented
by the formula (XXII) with an oxidizing agent in the
presence of a solvent.
The oxidizing agent to be used for the above
reaction may, for example, be hydrogen peroxide,
peracetic acid or m-chloroperbenzoic acid.
The solvent to be used for the above reaction may be
any solvent so long as it is inert to the reaction.

Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; ketones such as acetone and dimethyl
ethyl ketone; ethers such as diethyl ether, dioxane and
tetrahydrofuran; and acetic acid. As the solvent, one or
more types may suitably be selected.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula (XXII)
can be produced in accordance with the following reaction
[R]

wherein R4, R6 and L are as defined above.
Namely, the compound represented by the above
formula (XXII) can be produced by reacting a compound
represented by the formula (XXIII) with an alkylthiol in
the presence of a solvent.
The solvent to be used for the above reaction may be
any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; ketones such as acetone and dimethyl

ethyl ketone; ethers such as diethyl ether, dioxane and
tetrahydrofuran; acetic acid; water; and N,N-
dimethylformamide, dimethylsulfoxide, sulfolane and
dimethoxyethane. As the solvent, one or more types may
suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either inorganic base or organic base. Examples of
the organic base include triethylamine,
diisopropylethylamine, pyridine, 4-
(dimethylamino)pyridine and 2,6-lutidine. Examples of
the inorganic base include alkali metal carbonates such
as sodium carbonate and potassium carbonate; alkali metal
hydrogencarbonates such as sodium hydrogencarbonate and
potassium hydrogencarbonate; alkaline earth metal
carbonates such as calcium carbonate and magnesium
carbonate; alkali metal hydroxides such as sodium
hydroxide; and alkali metal hydrides such as sodium
hydride and potassium hydride. As the base, one or more
types may suitably be selected and mixed.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 4 8 hours.
The compound represented by the above formula
(XXIII) can be produced by a known method. For example,
a compound wherein R4 is alkyl and R6 is alkylsulfonyl,
as disclosed in JP-A-11-240872, at page 9, and a compound

wherein R4 is halogen and R6 is alkylsulfonyl, as
disclosed in WO98/29392, at page 264, are known compounds,
and they can be produced in accordance with a method
disclosed in each publication or a method similar thereto.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-4 can be produced in
accordance with the following reaction [S].

wherein R4, R6 and L are as defined above, and R5-a-4 is
cyano.
Namely, the compound represented by the formula (XI-
a-4) can be produced by reacting a compound represented
by the formula (XXIV) with an acid anhydride such as
acetic anhydride or sulfonyl chloride such as
methanesulfonyl chloride.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; ketones such as' acetone and dimethyl
ethyl ketone; ethers such as diethyl ether, dioxane and

tetrahydrofuran; and pyridine. As the solvent, one or
more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. Examples of
the base include triethylamine, N,N-dimethylaminopyridine
and diisopropylaminopyridine. As the base, one or more
types may suitably be selected and mixed.
The above reaction can be carried out at a reaction
temperature of usually from 0 to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula (XXIV)
can be produced in accordance with the following reaction
[T] .

wherein R4, R6 and L are as defined above.
Namely, the compound represented by the formula
(XXIV) can be produced by reacting a compound represented
by the formula (XX) with hydroxyamine or hydroxyamine
hydrochloride in the presence of a solvent.
The solvent to be used for the above reaction may be
any solvent so long as it is inert to the reaction.
Examples thereof include alcohols such as methanol and

ethanol; halogenated hydrocarbons such as methylene
chloride, chloroform, dichloroethane and trichloroethane;
ketones such as acetone and dimethyl ethyl ketone; and
ethers such as diethyl ether, dioxane and tetrahydrofuran.
As the solvent, one or more types may suitably be
selected.
The above reaction can be carried out in the
presence of an acid or a base, as the case requires.
Examples of the acid include p-toluenesulfonic acid.
Examples of the base include sodium acetate.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-5 can be produced in
accordance with the following reaction [U].

wherein R4, R6 and L are as defined above, and R5-a-5 is
cyanoalkyl.
Namely, the compound represented by the formula (XI-
a-5) can be produced by reacting a compound represented
by the formula (XXV) with an acid anhydride such as
acetic anhydride or sulfonyl chloride such as

methanesulfonyl chloride. This reaction can be carried
out in the same manner as the above-described reaction
[S] .
The compound represented by the above formula (XXV)
can be produced in accordance with the following reaction
[V] .

wherein R4, R6 and L are as defined above.
Namely, the compound represented by the formula
(XXV) can be produced by reacting a compound represented
by the formula (XXVI) with hydroxyamine or hydroxyamine
hydrochloride in the presence of a solvent. This
reaction can be carried out in the same manner as the
above-described reaction [T].
The compound represented by the above formula (XXVI)
can be produced in accordance with the following reaction
[W] .


wherein R4, R6 and L are as defined above, and A is alkyl.
Namely, the compound represented by the formula
(XXVI) can be produced by reacting a compound of the
formula (XXVII) with an acid such as hydrochloric acid.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction.
Examples thereof include water; alcohols such a methanol
and ethanol; and ethers such as diethyl ether, dioxane
and tetrahydrofuran. As the solvent, one or more types
may suitably be selected.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 4 8 hours.
The compound represented by the above formula
(XXVII) can be produced in accordance with the following
reaction [X].

wherein R4, R6, L and A are as defined above.
Namely, the compound represented by the formula
(XXVII) can be produced by reacting a compound
represented by the formula (XXVIII) with an alcohol in

the presence of an acid.
The alcohol to be used for the above reaction may,
for example, be methanol or ethanol. Further, the acid
may, for example, be hydrochloric acid or toluenesulfonic
acid.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 15 0°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula
(XXVIII) can be produced in accordance with the following
reaction [Y].

wherein R4, R6 and L are as defined above, T is halogen,
Ph is phenyl, and Me is methyl.
Namely, the compound represented by the formula
(XXVIII) can be produced by subjecting a compound
represented by the formula (XX) to Wittig reaction in the
presence of a solvent.
The solvent to be used for the above reaction may be
any solvent so long as it is inert to the reaction.
Examples thereof include ethers such as diethyl ether,
dioxane and tetrahydrofuran; aromatic hydrocarbons such

as benzene, toluene and xylene; and aprotic polar
solvents such as acetonitrile, N,N-dimethylformamide,
dimethylsulfoxide, sulfolane and dimethoxyethane.
The above reaction can be carried out in the
presence of a base, as the case requires. Examples of
the base include sodium hydride (NaH); alkali lithium
agents such as n-butyllithium; and metal amides such as
sodium amide (NaNH2) .
The above reaction can be carried out at a reaction
temperature of usually from -80°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-6 can be produced in
accordance with the following reaction [Z] .

wherein R4, R6 and L are as defined above, and R5-a-6 is
alkoxyalkoxyalkyl.
Namely, the compound represented by the formula (XI-
a-6) can be produced by reacting a compound represented
by the formula (XXIII) with an alkoxyalcohol.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction,

and examples thereof include alcohols such as methanol
and ethanol; esters such as methyl acetate, ethyl acetate
and propyl acetate; ethers such as diethyl ether, dioxane
and tetrahydrofuran; and aprotic polar solvents such as
acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane. As the solvent, one or
more may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. Examples of
the base include alkali metal hydrides such as sodium
hydride and potassium hydride.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula
(XXIII) can be produced by a known method. For example,
a compound wherein R4 is alkyl and R6 is alkylsulfonyl,
as disclosed in JP-A-11-240872, at page 9, and a compound
wherein R4 is halogen and R6 is alkylsulf onyl, as
disclosed in WO98/29392, at page 264, are known compounds,
and they can be produced in accordance with a method
disclosed in each publication or a method similar thereto.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-7 can be prepared in
accordance with the following reaction [AA].


wherein R4, R6 and L are as defined above, and R5-a-7 is
alkylthio, alkoxyalkylthio, haloalkoxyalkylthio,
alkoxyhaloalkylthio, haloalkoxyhaloalkylthio,
alkylthioalkylthio, haloalkylthioalkylthio,
alkylthiohaloalkylthio or haloalkylthiohaloalkylthio.
Namely, the compound represented by the formula (XI-
a-7) can be produced by reacting a thiol corresponding to
R5-a-7 with a compound represented by the formula (XXIX) .
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction,
and examples thereof include alcohols such as methanol
and ethanol,- ethers such as diethyl ether, dioxane and
tetrahydrofuran; aprotic polar solvents such as
acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and water. As the solvent,
one or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. Examples of
the base include alkali metal hydrides such as sodium
hydride and potassium hydride; alkali metal hydroxides
such as sodium hydroxide and potassium hydroxide; and

alkaline earth metal hydroxides such as calcium hydroxide.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 250°C for a reaction
time of usually from 1 minute to 48 hours.
The compound represented by the above formula (XXIX)
can be produced by a known method. For example, a
compound wherein R4 is halogen and R6 is alkylsulfonyl,
as disclosed in European Patent Publication No. 0195247,
at page 8, and a compound wherein R4 is alkyl and R6 is
alkylsulfonyl, as disclosed in Pest Management Science
(2002), 58(12), 1175 to 1186, are known compounds, and
they can be produced in accordance with a method
disclosed in the publication or a method similar thereto.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-8 can be prepared in
accordance with following reaction [AB].

wherein R4, R6 and L are as defined above, and R5-a-8 is a
heterocyclylalkyl containing two oxygen atoms.
Namely, the compound represented by the formula (XI-
a-8) can be produced by reacting an alkylene glycol with
a compound represented by the formula (XXVI) in the

presence of a solvent and an acid catalyst.
The solvent to be used for the above reaction may be
any solvent so long as it is inert to the reaction.
Examples thereof include halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene, esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The acid catalyst to be used for the above reaction
may, for example, be p-toluenesulfonic acid or pyridium
p-toluenesulfonate.
In the above reaction, it is preferred to remove
moisture generated by the reaction by azeotropy with the
solvent or by using a drying agent.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds represented by the above formula
(II), a compound wherein R5 is R5-a-9 can be prepared in
accordance with the following reaction [AC] .


wherein R1, R2, R4 and R6 are as defined above, and R5-a-9
is thiocyanatoalkyl.
Namely, the compound represented by the formula (II-
a-9) can be produced by reacting NaSCN with a compound
represented by the formula (II-a-10).
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
to be used for the above reaction may be any solvent so
long as it is inert to the reaction. Examples thereof
include halogenated hydrocarbons such as methylene
chloride, chloroform, dichloroethane and trichloroethane;
aromatic hydrocarbons such as benzene, toluene and xylene,
esters such as methyl acetate, ethyl acetate and propyl
acetate; aprotic polar solvents such as acetonitrile,
N,N-dimethylformamide, dimethylsulfoxide, sulfolane and
dimethoxyethane; ethers such as diethyl ether, dioxane
and tetrahydrofuran; and alcohols such as methanol,
ethanol and propanol. As the solvent, one or more types
may suitably be selected.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction

time of usually from 1 minute to 48 hours.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-10 can be prepared in
accordance with the following reaction [AD].

wherein R4, R5-a-5, R6 and L are as defined above, and R5-a-
10 is amino(thiocarbonyl)alkyl which may be substituted
by at least one substituent selected from alkyl, cyano,
cyanoalkyl, (alkylthio) carbonylalkyl,
alkyl(thiocarbonyl)alkyl, -C(O)OR7 and -C(O)SR7.
Namely, the compound represented by the formula (XI-
a-10) can be produced by reacting P2S5 with a compound
represented by the formula (XI-a-5) in the presence of a
solvent.
The solvent to be used for the above reaction may be
any solvent so long as it is inert to the reaction, and
examples thereof include alcohols such as methanol,
ethanol and propanol; halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and
trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene; esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,

sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 250°C for a reaction
time of usually from 1 minute to 48 hours.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-11 can be prepared in
accordance with the following reaction [AE].

wherein R4, R6 and L are as defined above, and R5-a-11 is
aminoalkyl which may be substituted by at least one
substituent selected from alkyl, cyano, cyanoalkyl,
(alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl,
-C(O)OR7 and -C(O)SR7.
Namely, the compound represented by the formula (XI-
a-11) can be produced by reacting ammonia or an amine
which may be substituted by at least one substituent
selected from alkyl, cyano, cyanoalkyl,
(alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl,
-C(O)OR7 and -C(O)SR7, with a compound represented by the
formula (XXIII).
The above reaction can be carried out in the

presence of a solvent, as the case requires. The solvent
to be used for the above reaction may be any solvent so
long as it is inert to the reaction. Examples thereof
include halogenated hydrocarbons such as methylene
chloride, chloroform, dichloroethane and trichloroethane;
aromatic hydrocarbons such as benzene, toluene and xylene,
esters such as methyl acetate, ethyl acetate and propyl
acetate; aprotic polar solvents such as acetonitrile,
N,N-dimethylformamide, dimethylsulfoxide, sulfolane and
dimethoxyethane; and ethers such as diethyl ether,
dioxane and tetrahydrofuran. As the solvent, one or more
types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either inorganic base or organic base. Examples of
the inorganic base include alkali metal carbonates such
as sodium carbonate and potassium carbonate; alkali metal
hydrogencarbonates such as sodium hydrogencarbonate and
potassium hydrogencarbonate; alkaline earth metal
carbonates such as calcium carbonate and magnesium
carbonate; sodium hydride (NaH); alkali lithium reagents
such as n-butyllithium; and metal amides such as sodium
amide (NaNH2) . Examples of the organic base include
amines such as triethylamine, N,N-dimethylaminopyridine,
diisopropylaminopyridine and DBU (diazabicycloundecene).
The above reaction can be carried out in the
presence of a catalyst, as the case requires. The

catalyst may, for example, be TBAI (tert-butylammonium
iodide).
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 4 8 hours.
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-12 can be prepared in
accordance with the following reaction [AF-1].

wherein R4, R6, R5-a-11 and L are as defined above, and R5-a-
12 is one having the amino moiety of R5-a-11 substituted by
alkyl or cyanoalkyl.
Namely, the compound represented by the formula (XI-
a-12) can be produced by reacting a compound represented
by the formula (XI-a-11) with an alkyl halide or a
cyanoalkyl halide.
The above reaction can be carried out in the
presence of a solvent, as the case requires. The solvent
may be any solvent so long as it is inert to the reaction,
and examples thereof include alcohols such as methanol,
ethanol and propanol; halogenated hydrocarbons such as
methylene chloride, chloroform, dichloroethane and

trichloroethane; aromatic hydrocarbons such as benzene,
toluene and xylene; esters such as methyl acetate, ethyl
acetate and propyl acetate; aprotic polar solvents such
as acetonitrile, N,N-dimethylformamide, dimethylsulfoxide,
sulfolane and dimethoxyethane; and ethers such as diethyl
ether, dioxane and tetrahydrofuran. As the solvent, one
or more types may suitably be selected.
The above reaction can be carried out in the
presence of a base, as the case requires. The base may
be either inorganic base or organic base. Examples of
the inorganic base include alkali metal carbonates such
as sodium carbonate and potassium carbonate; alkali metal
hydrogencarbonates such as sodium hydrogencarbonate and
potassium hydrogencarbonate; and alkaline earth metal
carbonates such as calcium carbonate and magnesium
carbonate. Examples of the organic base include amines
such as triethylamine, N,N-dimethylaminopyridine,
diisopropylaminopyridine and DBU (diazabicycloundecene).
The above reaction can be carried out at a reaction
temperature of usually from 0°C to 150°C for a reaction
time of usually from 1 minute to 4 8 hours.
Among the compounds represented by the above formula
(I), a compound wherein R5 is R5-a-13 can be prepared in
accordance with the following reaction [AF-2].


wherein R1, R2, R4, R6, R5-a-11 and Z are as defined above,
and R5-a-13 is one having the amino moiety of R5-a-11
substituted by (alkylthio)carbonyl.
Namely, the compound represented by the formula (I-
a-13) can be produced by reacting a compound represented
by the formula (II-a-11) with a compound represented by
the formula (Ill-a). This reaction can be carried out in
the same manner as the above-described reaction [A].
Among the compounds represented by the above formula
(XI) , a compound wherein R5 is R5-a-14 can be prepared in
accordance with the following reaction [AG] .

wherein R4, R6, L, T and Ph are as defined above, and R5-a-
14 is cyanoalkenyl.
Namely, the compound represented by the formula (XI-
a-15) can be produced by subjecting a compound
represented by the formula (XX) to Wittig reaction in the

presence of a solvent. This reaction can be carried out
in the same manner as the above-described reaction [Y].
The compounds of the present invention have
excellent herbicidal effects when used as an active
ingredient of herbicides. The application range extends
to agricultural fields such as paddy fields, crop plant
fields, orchards and mulberry fields and non-agricultural
fields such as forest land, farm roads, play grounds and
factory sites. The application method may suitably be
selected from soil application, foliar application, water
application, etc.
The compounds of the present invention are capable
of controlling a wide range of undesired plants such as
grasses (or gramineae) such as barnyardgrass (Echinochloa
crus-galli L.), early watergrass (Echinochloa oryzicola
vasing), crabgrass (Digitaria sanguinalis L.),
greenfoxtail (Setaria viridis L.), giant foxtail (Setaria
faberi Herrm.), goosegrass (Eleusine indica L.), wild oat
(Avena fatua L.) , johnsongrass (Sorghum halepense L.),
quackgrass (Agropyron repens L.), alexandergrass
(Brachiaria plantaginea), paragrass (Panicum
purpurascens) , sprangletop (Leptochloa chinensis), red
sprangletop (Leptochloa panicea), annual bluegrass (Poa
annua L.) , black grass (Alopecurus tnyosuroides Huds. ) and
cholorado bluestem (Agropyron tsukushiense (Honda) Ohwi),
sedges (or Cyperaceae) such as rice flatsedge (Cyperus
iria L.), purple nutsedge (Cyperus rotundus L.), yellow

nutsedge (Cyperus esculentus L.), Japanese bulrush
(Scirpus juncoides), flatsedge (Cyperus serotinus),
small-flower umbrellaplant (Cyperus difformis), slender
spikerush (Eleocharis acicularis) and water chestnut
(Eleocharis kuroguwai), alismataceae such as Japanese
ribbon waparo (Sagittaria pygmaea), arrow-head
(Sagittaria trifolia) and narrowleaf waterplantain
(Alisma canaliculatum), pontederiaceae such as monochoria
(Monochoria Vaginalis) and monochoria species (Monochoria
korsakowii), scrophulariaceae such as false pimpernel
(Lindernia pyxidaria) and abunome (Dopatrium junceum),
lythraceae such as toothcup (Rotala india) and red stem
(Ammannia multiflora), and other broad leaves such as
velvetleaf (Abutilon theophrasti MEDIC), tall
morningglory (Ipomoea purpurea L.), common lambsquarters
(Chenopodium album L.), prickly sida (Sida spinosa L.),
common purslane (Portulaca oleracea L.), slender amaranth
(Amaranthus viridis L.), redroot pigweed (Amaranthus
retroflexus L.), sicklepod (Cassia obtusifolia L.), black
nightshade (Solanum nigrum L.), pale smartweed (Polygonum
lapathifolium L. ) , common chickweed (Stellaria media L.),
long stem waterwort (Elatine triandra SCHK.), common
cocklebur (Xanthium strumarium L.), flexuous bittercress
(Cardamine flexuosa WITH.), henbit (Lamium amplexicaule
L.), common ragweed (Ambrosia elatior L.), catchweed
(Galium spurium L.), field bindweed (Calystegia arvensis
L. ), jimsonweed (Datura stramonium), thistle (Breea

setosa (BIEB.)KITAM.) and threeseeded copperleaf
(Acalypha australis L.). Therefore, they can be
effectively used for selectively controlling noxious
weeds or nonselectively controlling noxious weeds in
cultivation of useful crops such as corn (Zea mays L.),
soybean (Glycine max Merr.), cotton (Gossypium spp.),
wheat (Triticum spp.), rice (Oryza sativa L.), barley
(Hordeum vulgare L.), oat (Avena sativa L.), sorgo
(Sorghum bicolor Moench), rape (Brassica napus L.),
sunflower (Helianthus annuus L.), sugar beet (Beta
vulgaris L.), sugar cane (Saccharum officinarum L.),
Japanese lawngrass (Zoysia japonica stend), peanut
(Arachis hypogaea L.), flax (Linum usitatissimum L.),
tobacco (Nicotiana tabacum L.), and coffee (Coffea spp.).
Particularly, the compounds of the present invention are
effectively used for selectively controlling noxious
weeds in cultivation of corn, soybean, cotton, wheat,
rice, rape, sunflower, sugar beet, sugar cane, Japanese
lawngrass, peanut, flax, tobacco, coffee, and the like,
and among these, especially corn, soybean, wheat, rice
and the like.
The compound of the present invention may be mixed
with various agricultural additives and applied in the
form of various formulations such as dusts, granules,
water dispersible granules, wettable powders, tablets,
pills, capsules (including a formulation packaged by a
water soluble film), water-based suspensions, oil-based

suspensions, microemulsions, suspoemulsions, water
soluble powders, emulsifiable concentrates, soluble
concentrates or pastes. It may be formed into any
formulation which is commonly used in this field, so long
as the object of the present invention is thereby met.
The additives to be used for the formulation include,
for example, a solid carrier such as diatomaceous earth,
slaked lime, calcium carbonate, talc, white carbon,
kaoline, bentonite, a mixture of kaolinite and sericite,
clay, sodium carbonate, sodium bicarbonate, mirabilite,
zeolite or starch; a solvent such as water, toluene,
xylene, solvent naphtha, dioxane, acetone, isophorone,
methyl isobutyl ketone, chlorobenzene, cyclohexane,
dimethyl sulfoxide, N,N-dimethylformamide,
dimethylacetamide, N-methyl-2-pyrrolidone or an alcohol;
an anionic surfactant such as a salt of fatty acid, a
benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate,
a polycarboxylate, a salt of alkylsulfuric acid ester, an
alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol
ether sulfate, a salt of alcohol sulfuric acid ester, an
alkyl sulfonate, an alkylaryl sulfonate, an aryl
sulfonate, a lignin sulfonate, an alkyldiphenyl ether
disulfonate, a polystyrene sulfonate, a salt of
alkylphosphoric acid ester, an alkylaryl phosphate, a
styrylaryl phosphate, a salt of polyoxyethylene alkyl
ether sulfuric acid ester, a polyoxyethylene alkylaryl
ether sulfate, a salt of polyoxyethylene alkylaryl ether

sulfuric acid ester, a polyoxyethylene alkyl ether
phosphate, a salt of polyoxyethylene alkylaryl phosphoric
acid ester, a salt of polyoxyethylene aryl ether
phosphoric acid ester, a naphthalene sulfonate condensed
with formaldehyde or an alkylnaphthalene sulfonate
condensed with formaldehyde; a nonionic surfactant such
as a sorbitan fatty acid ester, a glycerin fatty acid
ester, a fatty acid polyglyceride, a fatty acid alcohol
polyglycol ether, acetylene glycol, acetylene alcohol, an
oxyalkylene block polymer, a polyoxyethylene alkyl ether,
a polyoxyethylene alkylaryl ether, a polyoxyethylene
styrylaryl ether, a polyoxyethylene glycol alkyl ether,
polyethylene glycol, a polyoxyethylene fatty acid ester,
a polyoxyethylene sorbitan fatty acid ester, a
polyoxyethylene glycerin fatty acid ester, a
polyoxyethylene hydrogenated castor oil or a
polyoxypropylene fatty acid ester; and a vegetable oil or
mineral oil such as olive oil, kapok oil, castor oil,
palm oil, camellia oil, coconut oil, sesame oil, corn oil,
rice bran oil, peanut oil, cottonseed oil, soybean oil,
rapeseed oil, linseed oil, tung oil or liquid paraffins.
These additives may suitably be selected for use alone or
in combination as a mixture of two or more of them, so
long as the object of the present invention is met.
Further, additives other than the above-mentioned may be
suitably selected for use among those known in this field.
For example, various additives commonly used, such as a

filler, a thickener, an anti-settling agent, an anti-
freezing agent, a dispersion stabilizer, a safener, an
anti-mold agent, a bubble agent, a disintegrator and a
binder, may be used. The mix ratio by weight of the
compound of the present invention to such various
additives may be from 0.1:99.9 to 95:5, preferably from
0.2 :99.8 to 85:15.
The dose of the herbicide containing the compound of
the present invention can not generally be defined, as it
varies depending upon the weather conditions, the soil
conditions, the type of the formulation, the type of the
weeds to be controlled, the application season, etc.
However, it is usually applied in an amount of the
compound of the present invention of from 0.5 to 5,000 g,
preferably from 1 to 1,000 g, more preferably from 10 to
500 g, per hectare. The present invention includes such
a method for controlling undesired weeds, by such
applications of the herbicide.
Further, the herbicide containing compound of the
present invention may be mixed with or may be used in
combination with other agricultural chemicals,
fertilizers or phytotoxicity-reducing agents, whereby
synergistic effects or activities may sometimes be
obtained. Such other agricultural chemicals include, for
example, a herbicide, a fungicide, an antibiotic, a plant
hormone and an insecticide. Especially, with a mixed
herbicidal composition having a compound of the present

invention mixed with or used in combination with one or
more active compounds of other herbicides, the range of
weeds to be controlled, the time of application of the
composition, the herbicidal activities, etc. may be
improved to preferred directions. The compound of the
present invention and the active compounds of other
herbicides may separately be formulated so that they may
be mixed for use at the time of application, or they may
be formulated together. The present invention includes
such a mixed herbicidal composition.
The mixing ratio of the compound of the present
invention to the active compounds of other herbicides can
not generally be defined, since it varies depending upon
the weather conditions, the soil conditions, the types of
formulations, the application time, the application
method, etc., but the other herbicides are mixed in an
amount of from 0.001 to 10,000 parts by weight,
preferably from 0.01 to 1,000 parts by weight per one
type of the active compound, based on 1 part by weight of
the compound of the present invention. Further, the dose
for the application is such that the total amount of the
active compounds is from 0.1 to 10,000 g, preferably from
0.2 to 5,000 g, more preferably from 10 to 3,000 g, per
hectare. The present invention includes a method for
controlling undesired weeds by application of such a
mixed herbicidal composition.
Another herbicidally active compound includes, for

example, the following compounds (common names including
ones under application for approval by ISO). Even when
not specifically mentioned here, in a case where such
compounds have salts, alkyl esters, etc., they are, of
course, all included.
(1) Those which are believed to exhibit herbicidal
effects by disturbing hormone activities of plants, such
as a phenoxy type such as 2,4-D, 2,4-DB, 2,4-DP, MCPA,
MCPB, MCPP, naproanilide or clomeprop, an aromatic
carboxylic acid type such as 2,3,6-TBA, dicamba,
dichlobenil, picloram, triclopyr, clopyralid or
aminopyralid, and others such as naptalam, benazolin,
quinclorac, quinmerac, diflufenzopyr and thiazopyr.
(2) Those which are believed to exhibit herbicidal
effects by inhibiting photosynthesis of plants, such as a
urea type such as chlorotoluron, diuron, fluometuron,
linuron, isoproturon, metobenzuron or tebuthiuron, a
triazine type such as simazine, atrazine, atratone,
simetryn, prometryn, dimethametryn, hexazinone,
metribuzin, terbuthylazine, cyanazine, ametryn,
cybutryne, triaziflam or propazine, a uracil type such as
bromacil, lenacil or terbacil, an anilide type such as
propanil or cypromid, a carbamate type such as swep,
desmedipham or phenmedipham, a hydroxybenzonitrile type
such as bromoxynil, bromoxynil-octanoate or ioxynil, and
others such as pyridate, bentazone, amicarbazone and
methazole.

(3) Quaternary ammonium salt type such as paraquat
or diquat, which is believed to be converted to free
radicals by itself to form active oxygen in the plant
body.
(4) Those which are believed to exhibit herbicidal
effects by inhibiting chlorophyll biosynthesis of plants
and abnormally accumulating a photosensitizing peroxide
substance in the plant body, such as a diphenylether type
such as nitrofen, chlomethoxyfen, bifenox, acifluorfen-
sodium, fomesafen, oxyfluorfen, lactofen or ethoxyfen-
ethyl, a cyclic imide type such as chlorphthalim,
flumioxazin, flumiclorac-pentyl or fluthiacet-methyl, and
others such as oxadiargyl, oxadiazon, sulfentrazone,
carfentrazone-ethyl, thidiazimin, pentoxazone,
azafenidin, isopropazole, pyraflufen-ethyl,
benzfendizone, butafenacil, metobenzuron, cinidon-ethyl,
flupoxam, fluazolate, profluazol, pyrachlonil, flufenpyr-
ethyl and bencarbazone.
(5) Those which are believed to exhibit herbicidal
effects characterized by bleaching activities by
inhibiting chromogenesis of plants such as carotenoids,
such as a pyridazinone type such as norflurazon,
chloridazon or metflurazon, a pyrazole type such as
pyrazolate, pyrazoxyfen, benzofenap, topraraezone (BAS-
670H) or pyrasulfotole, and others such as amitrol,
fluridone, flurtamone, diflufenican, methoxyphenone,
clomazone, sulcotrione, mesotrione, tembotrione,

tefuryltrione (AVH-3 01), isoxaflutole, difenzoquat,
isoxachlortole, benzobicyclon, picolinafen and
beflubutamid.
(6) Those which exhibit strong herbicidal effects
specifically to gramineous plants, such as an
aryloxyphenoxypropionic acid type such as diclofop-
methyl, flamprop-M-methyl, pyriphenop-sodium, fluazifop-
butyl , haloxyfop-methyl, quizalofop-ethyl, cyhalofop-
butyl , fenoxaprop-ethyl or metamifop-propyl, and a
cyclohexanedione type such as alloxydim-sodium,
clethodim, sethoxydim, tralkoxydim, butroxydim,
tepraloxydim, caloxydim, clefoxydim or profoxydim.
(7) Those which are believed to exhibit herbicidal
effects by inhibiting an amino acid biosynthesis of
plants, such as a sulfonylurea type such as chlorimuron-
ethyl, sulfometuron-methyl, primisulfuron-methyl,
bensulfuron-methyl, chlorsulfuron, metsulfuron-methyl,
cinosulfuron, pyrazosulfuron-ethyl, azimsulfuron,
flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron,
cyclosulfamuron, prosulfuron, flupyrsulfuron,
triflusulfuron-methyl, halosulfuron-methyl,
thifensulfuron-methyl, ethoxysulfuron, oxasulfuron,
ethametsulfuron, iodosulfuron, sulfosulfuron,
triasulfuron, tribenuron-methyl, tritosulfuron,
foramsulfuron, trifloxysulfuron, mesosulfuron-methyl,
orthosulfamuron, flucetosulfuron, amidosulfuron, TH-547,
a compound disclosed in WO2005092104, a

triazolopyrimidinesulfonamide type such as flumetsulam,
metosulam, diclosulam, cloransulam-methyl, florasulam,
metosulfam or penoxsulam, an imidazolinone type such as
imazapyr, imazethapyr, imazaquin, imazamox, imazameth,
imazamethabenz or imazapic, a pyrimidinylsalicylic acid
type such as pyrithiobac-sodium, bispyribac-sodium,
pyriminobac-methyl, pyribenzoxim, pyriftalid or
pyrimisulfan (KUH-021), a
sulfonylaminocarbonyltriazolinone type such as
flucarbazone or procarbazone-sodium, and others such as
glyphosate, glyphosate-sodium, glyphosate-potassium,
glyphosate-ammonium, glyphosate-isopropylamine,
sulfosate, glufosinate, glufosinate-ammonium and
bilanafos.
(8) Those which are believed to exhibit herbicidal
effects by inhibiting cell mitoses of plants, such as a
dinitroaniline type such as trifluralin, oryzalin,
nitralin, pendimethalin, ethalfluralin, benfluralin or
prodiamine, an amide type such as bensulide, napronamide
or pronamide, an organic phosphorus type such as
amiprofos-methyl, butamifos, anilofos or piperophos, a
phenylcarbamate type such as propham, chlorpropham or
barban, a cumylamine type such as daimuron, cumyluron or
bromobutide, and others such as asulam, dithiopyr and
thiazopyr.
(9) Those which are believed to exhibit herbicidal
effects by inhibiting protein biosynthesis or lipid

biosynthesis of plants, such as a chloroacetamide type
such as alachlor, metazachlor, butachlor, pretilachlor,
metolachlor, S-metolachlor, thenylchlor, pethoxamid,
acetochlor, propachlor or propisochlor, a carbamate type
such as molinate, dimepiperate or pyributicarb, and
others such as etobenzanid, mefenacet, flufenacet,
tridiphane, cafenstrole, fentrazamide, oxaziclomefone,
indanofan, dimethenamid, benfuresate and pyroxasulfone
(KIH-485).
(10) A thiocarbamate type such as EPTC, butylate,
vernolate, pebulate, cycloate, prosulfocarb, esprocarb,
thiobencarb, diallate or triallate, and others such as
MSMA, DSMA, endothall, ethofumesate, sodium chlorate,
pelargonic acid, fosamine, pinoxaden and HOK-201.
(11) Those which are believed to exhibit herbicidal
effects by being parasitic on plants, such as Xanthomonas
campestris, Epicoccosurus nematosurus, Exserohilum
monoseras and Drechsrela monoceras.
Examples of preferred embodiments of the present
invention are shown below, but the present invention is
by no means restricted thereto.
(1) A benzoylpyrazole compound of the above formula (I),
wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom
or alkyl, R3 is alkyl; cycloalkyl; haloalkyl;
alkoxyalkyl; alkenyl; or arylalkyl which may be
substituted by R8, R4 is alkyl; haloalkyl; alkoxy;
halogen; nitro; cyano; alkylthio; alkylsulfinyl; or

alkylsulfonyl, R5 is a hydrogen atom; alkyl; halogen;
cyano; cyanoalkyl; haloalkyl; alkoxyalkyl;
haloalkoxyalkyl; alkoxy; haloalkoxy; alkoxyalkoxy;
haloalkoxyalkoxy; alkoxyhaloalkoxy; alkoxyalkoxyalkyl;
alkylthio; alkoxyalkylthio; haloalkoxyalkylthio;
alkylthioalkylthio; haloalkylthioalkylthio;
alkylthioalkoxy; alkylsulfonyl; alkylsulfonylalkyl;
alkoxycarbonylalkyl; alkoxycarbonylalkoxy;
heterocyclyloxy; heterocyclylalkoxy;
heterocyclylalkoxyalkyl; -OC(O)SR7; -OC(O)OR7; -C(O)OR7;
-C(O)SR7; or 4,5-dihydroisoxazol-3-yl which may be
substituted by R9, R6 is haloalkyl; halogen; nitro;
cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R7 is
alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl;
alkynyl; or arylalkyl which may be substituted by R10,
and each of R8, R9 and R10 which are independent of one
another, is halogen; alkyl; or alkoxy, or its salt, a
process for producing it, a herbicide containing it as an
active ingredient, and a method for controlling undesired
plants or inhibiting their growth, which comprises
applying a herbicidally effective amount of it to the
undesired plants or to a place where they grow.
(2) A benzoylpyrazole compound of the above formula (I) ,
wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom
or alkyl, R3 is alkyl; cycloalkyl; haloalkyl;
alkoxyalkyl; or arylalkyl which may be substituted by R8,
R4 is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano;

alkylthio; alkylsulfinyl; or alkylsulfony, R5 is alkyl;
haloalkyl; alkoxyalkyl; haloalkoxyalkyl; alkoxy;
haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy;
heterocyclyloxy; heterocyclylalkoxy;
heterocyclylalkoxyalkyl; -OC(O)SR7; -0C(0)OR7; -C(O)OR7;
-C(O)SR7; or 4,5-dihydroisoxazol-3-yl which may be
substituted by R9, R6 is haloalkyl; halogen; nitro;
cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R7 is
alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl;
alkynyl; or arylalkyl which may be substituted by R10,
and each of R8, R9 and R10 which are independent of one
another, is halogen; alkyl; or alkoxy, or its salt, a
process for producing it, a herbicide containing it as an
active ingredient, and a method for controlling undesired
plants or inhibiting their growth, which comprises
applying a herbicidally effective amount of it to the
undesired plants or to a place where they grow.
(3) A benzoylpyrazole compound of the above formula (I)
wherein R1 is alkyl, R2 is a hydrogen atom, R3 is alkyl,
R4 is alkyl, R5 is alkoxy; haloalkoxy; -C(O)OR7; or 4,5-
dihydroisoxazol-3-yl, and R6 is alkylsulfonyl, or its
salt, a process for producing it, a herbicide containing
it as an active ingredient, and a method for controlling
undesired plants or inhibiting their growth, which
comprises applying a herbicidally effective amount of it
to the undesired plants or to a place where they grow.
(4) A mixed herbicidal composition containing the

benzoylpyrazole compound of the above formula (I) or its
salt, and one or more types of active compounds of other
herbicides, and a method for controlling undesired plants
or inhibiting their growth, which comprises applying a
herbicidally effective amount of such a composition to
the undesired plants or to a place where they grow.
Now, the present invention will be described in
detail with reference to Examples. However, it should be
understood that the present invention is by no means
restricted to such specific Examples.
Preparation Examples for compounds of the present
invention are described below.
PREPARATION EXAMPLE 1
Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-
4-yl 3-(methoxycarbonyl)-2-methyl-4-
(methylsulfonyl)phenyl ketone (Compound No. 1 as
described hereinafter)
5-Hydroxy-l-methylpyrazol-4-yl 3-(methoxycarbonyl) -
2-methyl-4-(methylsulfonyl)phenyl ketone (2 90 mg, 0.82
mmol) was dissolved in dry tetrahydrofuran (15 mL), and
triethylamine (166 mg, 1.64 mmol) was added thereto. A
solution (4 mL) of 96% S-ethyl chlorothiolformate (107
mg) dissolved in dry tetrahydrofuran was added thereto
little by little under cooling with ice water. The
reaction mixture was stirred for 90 minutes while the
reaction temperature was allowed to warm to room
temperature. The reaction solution was poured into ice

water, followed by extraction with ethyl acetate. The
extract was dried over anhydrous sodium sulfate, and the
solvent was distilled off under reduced pressure. The
residue was purified by silica gel column chromatography
(n-hexane:ethyl acetate=6:4) to obtain the desired
product as an amorphous solid (202 mg, 0.46 mmol) (yield:
56%) .
PREPARATION EXAMPLE 2
Preparation of l-ethyl-5-(ethylthio)carbonyloxypyrazol-4-
yl 3 -(methoxycarbonyl)-2-methyl-4 -(methylsulfonyl)phenyl
ketone (Compound No. 2 as described hereinafter)
5-Hydroxy-l-ethylpyrazol-4-yl 3-(methoxycarbonyl)-2-
methyl-4-(methylsulfonyl)phenyl ketone (510 mg, 1.3 9
mmol) was dissolved in dry tetrahydrofuran (20 mL), and
triethylamine (281 mg, 2.78 mmol) was added thereto. A
solution (4 mL) of 96% S-ethyl chlorothiolformate (217
mg) dissolved in dry tetrahydrofuran was added thereto
little by little under cooling with ice water. The
reaction mixture was stirred for 90 minutes while the
reaction temperature was allowed to warm to room
temperature. The reaction mixture was poured into ice
water, followed by extraction with ethyl acetate. The
organic layer was dried over anhydrous sodium sulfate,
and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column
chromatography (n-hexane:ethyl acetate=6:4) to obtain the
desired product as an oil (417 mg, 0.92 mmol) (yield:

66%) .
PREPARATION EXAMPLE 3
Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-
4-yl 3-(methoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone
(Compound No. 35 as described hereinafter)
(1) To a stirred mixture of 3-methoxy-2-methyl-4 -
(methylsulfonyl)benzoic acid (340 mg, 1.39 mmol) and 5-
hydroxy-1-methylpyrazole hydrochloride (230 mg) in
anhydrous methylene chloride (10 mL) were added DCC
(dicyclohexylcarbodiimide) (315 mg) and triethylamine
(260 mg) at room temperature, followed by stirring for 2
hours. The reaction mixture was subjected to filtration
through Celite, the filtrate was concentrated, and the
obtained residue was dissolved in 10 mL of anhydrous
acetonitrile. Triethylamine (260 mg) and acetone
cyanohydrin in a catalytic amount were added thereto, and
the reaction solution was stirred overnight at room
temperature. 15 0 mL of ethyl acetate was added, and the
solution was washed once with a IN hydrochloric acid
aqueous solution and washed once with a saturated brine.
The organic layer was dried over anhydrous sodium sulfate,
and then the solvent was distilled off under reduced
pressure. The obtained residue was purified by silica
gel column chromatography (ethyl acetate:methanol=9:1) to
obtain 5-hydroxy-l-methylpyrazol-4-yl 3-methoxy-2-methyl-
4-(methylsulfonyl)phenyl ketone (115 mg).
1H-NMR(400MHz CDC13 ppm) :2.31(s, 3H) , 3.20 (s, 3H) ,

3.66(s, 3H) , 3.92(s, 3H) , 7.1(brs, 1H) , 7.29(d, 1H,
J=7.6Hz), 7.30(s, 1H), 7.85(d, 1H, J=7.6Hz).
(2) To a solution of 5-hydroxy-l-methylpyrazol-4-yl 3-
methoxy-2-methyl-4-(methylsulfonyl)phenyl ketone (100 mg,
0.3 mmol) in dry tetrahydrofuran (5 mL) were added
triethylamine (61 mg) and 96% S-ethyl chlorothiolformate
(50 mg) at room temperature. After the reaction solution
was stirred for 1 hour, 150 mL of ethyl acetate was added.
The mixture was washed twice with a saturated brine, the
organic layer was dried over anhydrous sodium sulfate,
and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column
chromatography (n-hexane:ethyl acetate=2:l) to obtain the
desired product as an oil.
PREPARATION EXAMPLE 4
Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-
4-yl 2-methyl-4-(methylsulfonyl)-3-(4,5-dihydroisoxazol-
3-yl)phenyl ketone (Compound No. 3 9 as described
hereinafter)
To a solution of 5-hydroxy-l-methylpyrazol-4-yl 3-
(4,5-dihydroisoxazol-3-yl)-2-methyl-4-
(methylsulfonyl)phenyl ketone (100 mg, 2.75x10-4 mol) in
anhydrous tetrahydrofuran (5 mL) were added triethylamine
(55 mg) and 96% S-ethyl chlorothiolformate (45 mg) at
room temperature. After the reaction solution was
stirred for 1 hour, 150 mL of ethyl acetate was added,
and the solution was washed twice with a saturated brine.

The organic layer was dried over anhydrous sodium sulfate,
and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column
chromatography (n-hexane:ethyl acetate=6:4) to obtain the
desired product (82 mg) as an oil.
PREPARATION EXAMPLE 5
Preparation of 5-(ethylthio)carbonyloxy-l-methylpyrazol-
4-yl 3-(difluoromethoxy)-2-methyl-4-
(methylsulfonyl)phenyl ketone (Compound No. 3 8 as
described hereinafter)
(1) To a stirred mixture of 3 -(difluoromethoxy)-2-
methyl-4-(methylsulfonyl)benzoic acid (500 mg, 1.78 mmol)
and 5-hydroxy-l-methylpyrazole hydrochloride (2 88 mg) in
anhydrous acetonitrile (10 mL) were added l-ethyl-3-(3-
dimethylaminopropyl)carbodiimide hydrochloride (443 mg),
triethylamine (360 mg) and dimethylaminopyridine (217 mg)
at room temperature. After being stirred for 12 hours,
the reaction mixture was concentrated under reduced
pressure, and the residue was dissolved in 100 mL of
methylene chloride. This solution was washed with 100 mL
of water, and the organic layer was dried over anhydrous
sodium sulfate, and the solvent was distilled off under
reduced pressure. The residue was dissolved in 10 mL of
anhydrous acetonitrile, and triethylamine (260 mg) and
acetone cyanohydrin in a catalytic amount were added,
followed by stirring overnight at room temperature. 150
mL of methylene chloride was added, followed by

extraction with a IN potassium carbonate aqueous solution,
and the aqueous layer was acidified by 2N hydrochloric
acid. The obtained acidic aqueous solution was extracted
twice with methylene chloride (100 mL), the combined
organic layer was dried over anhydrous sodium sulfate,
and the solvent was distilled off under reduced pressure.
The obtained crude product was purified by silica gel
column chromatography (ethyl acetate:hexane=l:1 to 9:1)
to obtain 5-hydroxy-l-methylpyrazol-4-yl 3-
(difluoromethoxy)-2-methyl-4-(methylsulfonyl)phenyl
ketone as an oil.
1H-NMR(400MHz acetone-d6 ppm) : 2.37(s, 3H), 3.28(s,
3H), 3.61(s, 3H), 6.90(d, 1H, J=75.2Hz), 7.27(s, 1H),
7.59(d, 1H, J=8.4Hz), 7.96(d, 1H, J=8.4Hz).
(2) To a solution of 5-hydroxy-l-methylpyrazol-4-yl 3-
(difluoromethoxy)-2-methyl-4-(methylsulfonyl)phenyl
ketone (89 mg) in dry tetrahydrofuran (5 mL) were added
triethylamine (50 mg) and 96% S-ethyl chlorothiolformate
(4 0 mg) at room temperature. After the reaction solution
was stirred for 1 hour, 150 mL of ethyl acetate was added.
The mixture was washed twice with a saturated brine, the
organic layer was dried over anhydrous sodium sulfate,
and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column
chromatography (n-hexane:ethyl acetate=2:l) to obtain the
desired product as an oil.
PREPARATION EXAMPLE 6

Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-
4-yl 3 -(2-methoxyethoxy)-2-methyl-4-
(methylsulfonyl)phenyl ketone (Compound No. 55 as
described hereinafter)
(1) To a stirred suspension of sodium hydride (60%, 220
mg, 5.32 mmol) in anhydrous N,N-dimethyIformamide (10 mL)
was added methyl 3-hydroxy-2-methyl-4-
(methylsulfonyl)benzoate (1 g, 4.09 mmol) under nitrogen
atmosphere at room temperature. After stirring for 30
minutes, 2-bromoethyl methyl ether (1.13 g, 8.18 mmol)
and potassium iodide in a catalytic amount were added
thereto, and the reaction solution was stirred at 60°C
for 12 hours. 200 mL of ethyl acetate was added to the
reaction solution, and the solution was washed twice with
a saturate brine. The organic layer was dried over
anhydrous sodium sulfate and concentrated under reduced
pressure. The residue was purified by silica gel column
chromatography (n-hexane:ethyl acetate=l:2) to obtain
methyl 3-(2-methoxyethoxy)-2-methyl-4-
(methylsulfonyl)benzoate as an oil (680 mg).
1H-NMR 4 00MHz (CDC13 ppm) 2.53 (s, 3H) , 3.26(s, 3H) ,
3.46(s, 3H), 3.78(m, 2H), 3.91(s, 3H), 4.19(m, 2H),
7.71(d, 1H, J=8.4Hz), 7.84(d, 1H, J=8.4Hz).
(2) Methyl 3-(2-methoxyethoxy)-2-methyl-4-
(methylsulfonyl)benzoate (680 mg, 2.25 mmol) was
dissolved in methanol (10 mL), and an aqueous sodium
hydroxide solution (2 mL) at a concentration of 20% was

added thereto at room temperature. After stirring for 30
minutes, the solvent was removed under reduced pressure.
100 mL of IN hydrochloric acid was added to the residue,
followed by extraction with ethyl acetate (200 mL). The
organic layer was washed twice with a saturated brine and
dried over anhydrous sodium sulfate. The solvent was
distilled off under reduced pressure to obtain 3-(2-
methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid
(570 mg) as a white solid.
1H-NMR 400MHz(acetone-d6 ppm); 2.56 (s, 3H) ,
3.31(s, 3H) , 3.41(s, 3H) , 3.80(m, 2H) , 4.21(m, 2H) ,
7.81(s, 2H).
(3) To a solution of 3-(2-methoxyethoxy)-2-methyl-4-
(methylsulfonyl)benzoic acid (195 mg, 6.76 mmol) in
chloroform (15 mL) were added oxalyl chloride (0.5 mL)
and DMF in a catalytic amount. The reaction mixture was
stirred for 3 0 minutes at room temperature, and the
solvent was distilled off under reduced pressure. The
residue was dissolved in anhydrous THF (20 mL), and 5-
hydroxy-1-methylpyrazole hydrochloride (136 mg, 1.01
mmol), triethylamine (13 6 mg) and N,N-
dimethylaminopyridine (250 mg) were added, followed by
reflux with heating for 1 hour. The reaction mixture was
allowed to cool to room temperature, and diluted with
ethyl acetate (200 mL). The mixture was washed twice
with a saturated brine. The organic layer was dried over
anhydrous sodium sulfate, and the solvent was distilled

off under reduced pressure. The residue was dissolved in
anhydrous acetonitrile (10 mL), and triethylamine (136
mg) and acetone cyanohydrin in a catalytic amount were
added. The mixture was stirred for 12 hours at room
temperature. The solvent was distilled off under reduced
pressure to obtain crude 5-hydroxy-l-methylpyrazol-4-yl
3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl
ketone.
1H-NMR (400MHz CDC13 ppm); 2.39(s, 3H), 3.29(s,
3H) , 3.46(s, 3H) , 3.71(s, 3H) , 3.81(m, 2H) , 4.24(m, 2H) ,
7.34(s, 1H), 7.35(d, 1H, J=7.6Hz), 7.92(d, 1H, J=7.6Hz).
(4) The crude 5-hydroxy-l-methylpyrazol-4-yl 3-(2-
methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone
obtained in the above step (3) was dissolved in anhydrous
THF (10 mL), and triethylamine (190 mg) and 96% S-ethyl
chlorothiolformate (151 mg) were added, followed by
stirring for 1 hour at room temperature. Ethyl acetate
(200 mL) was added to the reaction mixture, and the
mixture was washed twice with a saturated brine. The
organic layer was dried over anhydrous sodium sulfate,
and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column
chromatography (n-hexane:ethyl acetate=l:l) to obtain the
desired product (2 50 mg).
PREPARATION EXAMPLE 7
Preparation of 5-(ethylthio)carbonyloxy-l-ethylpyrazol-4-
yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl

ketone (Compound No. 16 as described hereinafter)
(1) To a solution of 3-(2-methoxyethoxy)-2-methyl-4-
(methylsulfonyl)benzoic acid (200 mg, 6.90xl0-4 mol) in
chloroform (15 mL) were added oxalyl chloride (0.5 mL)
and DMF in a catalytic amount. The reaction mixture was
stirred at room temperature for 3 0 minutes, and the
solvent was distilled off under reduced pressure. The
residue was dissolved in anhydrous THF (20 mL), and 5-
hydroxy-1-ethylpyrazole hydrochloride (134 mg, 9.01xl0~4
mol), triethylamine (13 9 mg) and N,N-
dimethylaminopyridine (170 mg) were added. The mixture
was heated at refluxed temperature for 1 hour. The
reaction mixture was allowed to cool to room temperature,
and then ethyl acetate (2 00 mL) was added. The mixture
was washed twice with a saturated brine, and the organic
layer was dried over anhydrous sodium sulfate. The
solvent was distilled off under reduced pressure. The
residue was dissolved in anhydrous acetonitrile (10 mL),
and triethylamine (13 9 mg) and acetone cyanohydrin in a
catalytic amount were added, followed by stirring for 12
hours at room temperature. The solvent was distilled off
under reduced pressure to obtain crude 5-hydroxy-l-
ethylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-
(methylsulfonyl)phenyl ketone.
1H-NMR (400MHz CDC13 ppm) ; 1.40 (t, 3H, J=7.0Hz),
2.39(s, 3H) , 3.25(s, 3H) , 3.42(s, 3H) , 3.76(m, 2H) ,
4.02(q, 2H, J=7.0Hz), 4.20(m, 2H) , 7.28(s, 1H) , 7.31(d,

1H, J=7.6Hz), 7.87(d, 1H, J=7.6Hz).
(2) The crude 5-hydroxy-l-ethylpyrazol-4-yl 3-(2-
methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone
obtained in the above step (1) was dissolved in anhydrous
THF (10 mL), and triethylamine (139 mg) and 96% S-ethyl
chlorothiolformate (111 mg) were added, followed by
stirring for 1 hour at room temperature. Ethyl acetate
(200 mL) was added to the obtained reaction mixture, and
the mixture was washed twice with a saturated brine. The
organic layer was dried over anhydrous sodium sulfate,
and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column
chromatography (n-hexane:ethyl acetate=l:l) to obtain the
desired product (170 mg).
PREPARATION EXAMPLE 8
Preparation of 5-(ethylthio)carbonyloxy-1-methylpyrazol-
4-yl 3-(2,2-dimethoxyethoxy)-2-methyl-4-
(methylsulfonyl)phenyl ketone (Compound No. 209 as
described hereinafter)
(1) 3-Hydroxy-2-methyl-4-(methylsulfonyl)benzoic acid
(300 mg, 1.3 0 mmol) was dissolved in N,N-
dimethylformamide (10 mL) , and potassium carbonate (360
mg, 2.72 mmol) and bromoacetaldehyde dimethyl acetal (660
mg, 3.90 mmol) were added at room temperature. The
reaction mixture was heated at 80°C, followed by stirring
for 32 hours. The reaction mixture was allowed to cool
to room temperature, and 100 mL of water and a 0.5N

sodium hydroxide aqueous solution (10 mL) were added.
Then, extraction with ethyl acetate (200 mL) was carried
out, and the organic layer was dried over anhydrous
sodium sulfate. The solvent was distilled off under
reduced pressure to obtain 2,2-dimethoxyethyl 3-(2,2-
dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate as
an oil.
1H-NMR 400MHz (CDC13 ppm) : 2.54 (s, 3H) , 3.31 (s,
1H) , 3.39(s, 6H) , 3.44(s, 6H) , 4.06(d, 2H, J=5.4Hz),
4.31(d, 2H, J=5.4Hz), 4.73(t, 1H, J=5.4Hz), 4.87(t, 1H,
J=5.4Hz), 7.76(d, 1H, J=8.4Hz), 7.82(d, 1H, J=8.4Hz).
(2) The 2,2-dimethoxyethyl 3-(2,2-dimethoxyethoxy)-2-
methyl-4-(methylsulfonyl)benzoate obtained in the above
step (1) was dissolved in methanol (20 mL), and an
aqueous sodium hydroxide solution (2 mL) at a
concentration of 2 0% was added thereto at room
temperature. After stirring for 3 0 minutes, 10 0 mL of IN
hydrochloric acid was added to the reaction solution,
followed by extraction with ethyl acetate (200 mL). The
organic layer was washed twice with a saturated brine and
dried over anhydrous sodium sulfate. The solvent was
distilled off under reduced pressure to obtain 3-(2,2-
dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid
(390 mg) as a white solid.
1H-NMR 400MHz(acetone-d6 ppm) : 2.56 (s, 3H) ,
3.31(s, 3H), 3.44(s, 6H) , 4.06(d, 2H, J=5.2Hz), 4.88(t,
1H, J=5.2Hz), 7.82(br s, 2H) .

(3) 3-(2,2-Dimethoxyethoxy)-2-methyl-4-
(methylsulfonyl)benzoic acid (390 mg, 1.23 mmol) was
dissolved in chloroform (15 mL), and oxalyl chloride (0.5
mL) and DMF in a catalytic amount were added thereto.
The reaction mixture was stirred at room temperature for
30 minutes, and the solvent was distilled off under
reduced pressure. The residue was dissolved in anhydrous
THF (20 mL), and 5-hydroxy-l-methylpyrazole (132 mg, 1.35
mmol), triethylamine (250 mg) and N,N-
dimethylaminopyridine (3 00 mg) were added, followed by
reflux with heating for 1 hour. The reaction mixture was
allowed to cool to room temperature, and ethyl acetate
(200 mL) was added. The mixture was washed twice with a
saturated brine. The organic layer was dried over
anhydrous sodium sulfate, and the solvent was distilled
off under reduced pressure. The residue was dissolved in
anhydrous acetonitrile (10 mL), and triethylamine (250
mg) and acetone cyanohydrin in a catalytic amount were
added, followed by stirring for 12 hours at room
temperature. The solvent was distilled off under reduced
pressure to obtain crude 5-hydroxy-l-methylpyrazol-4-yl
3-(2,2-dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl
ketone.
1H-NMR (400MHz CDCl3 ppm) : 2.38(s, 3H) , 3.29 (s,
3H), 3.47(s, 6H), 3.70(s, 3H), 4.09(d, 2H, J=5.2Hz),
4.1(brs, 1H), 4.83(t, 1H, J=5.2Hz), 7.32(s, 1H), 7.35(d,
1H, J=8.4Hz), 7.9l(d, 1H, J=8.4Hz).

(4) The crude 5-hydroxy-l-methylpyrazol-4-yl 3-(2,2-
dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone
obtained in the above step (3) was dissolved in anhydrous
THF (10 mL), and triethylamine (250 mg) and 96% S-ethyl
chlorothiolformate (200 mg) were added, followed by
stirring for 1 hour at room temperature. Ethyl acetate
(2 00 mL) was added to the obtained reaction mixture, and
the mixture was washed twice with a saturated brine. The
organic layer was dried over anhydrous sodium sulfate,
and the solvent was distilled off under reduced pressure.
The residue was purified by silica gel column
chromatography (n-hexane:ethyl acetate=l:l) to obtain the
desired product (150 mg).
Now, typical examples of the compounds of the
present invention represented by the above formula (I)
are shown in Table 1, and their 1H-NMR spectrum data are
shown in Table 2. Further, typical examples of the
compounds represented by the formula (II) as
intermediates for preparation of the compounds of the
formula (I) are shown in Table 3, and their 1H-NMR
spectrum data are shown in Table 4. These compounds can
be prepared in accordance with the above Preparation
Examples or the above various processes for production of
the compounds of the present invention. In Tables 1 to 4,
No. represents the Compound No. In Tables 1 and 3, Me
represents a methyl group, Et an ethyl group, n-Pr a
normal-propyl group, i-Pr an isopropyl group, c-Pr a

cyclopropyl group, s-Bu a secondary butyl group, t-Bu a
tertiary butyl group, Ph a phenyl group, and Bn a benzyl
group, respectively.



























































































































































Now, Test Examples will be described.
TEST EXAMPLE 1
Upland field soil was put into a 1/170,000 hectare
pot, and seeds of various plants were sown. When the
respective plants reached predetermined leaf stage ((1)
barnyardgrass (Echinochloa crus-galli L.); 0.8 to 2.5
leaf stage, (2) crabgrass (Digitaria sanguinalis L.): 0.5
to 3.0 leaf stage, (3) greenfoxtail (Setaria viridis L.):
1.0 to 3.0 leaf stage, (4) redroot pigweed (Amaranthus
retroflexus L.): cotyledon stage to 2.0 leaf stage, (5)
prickly sida (Sida spinosa L.): cotyledon stage to 1.1
leaf stage, (6) velvetleaf (Abutilon theophrasti MEDIC.):

cotyledon stage to 1.5 leaf stage, (7) rice (Oryza sativa
L.): 1.0 to 2.5 leaf stage, (8) wheat (Triticum spp.):
1.7 to 3.4 leaf stage, (9) corn (Zea mays L.): 2.0 to 3.5
leaf stage, and (10) soybean (Glycine max Merr.): primary
leaf stage to 0.3 leaf stage), wettable powders or
emulsifiable concentrates of the compounds of the present
invention prepared in accordance with a conventional
preparation method, were weighed so that the active
ingredients became the prescribed amounts, and diluted
with water in an amount corresponding to 5 00 liter per 1
hectare. 0.1 vol% of an agricultural spreader was
further added to the respective diluted liquids, followed
by foliar treatment with a small sprayer.
On the 17th to 23rd day after application, the state
of growth of the respective plants was visually observed,
and the herbicidal effect was evaluated in accordance
with a growth inhibition rate (%) of 0 (equivalent to the
non-treated area) to 100% (complete kill). The results
are shown in Table 5.







TEST EXAMPLE 2
Upland field soil was put into a 1/170,000 hectare
pot, and seeds of various plants (barnyardgrass,
crabgrass, greenfoxtail, redroot pigweed, prickly sida,
velvetleaf, rice, wheat, corn and soybean) were sown. On
the day after sowing, wettable powders or emulsifiable
concentrates of the compounds of the present invention
prepared in accordance with a conventional preparation
method, were weighed so that the active ingredients
became the prescribed amounts, and diluted with water in
an amount corresponding to 500 liter per 1 hectare,
followed by soil application with a small sprayer.
On the 19th to 24th day after the application, the
state of growth of the respective plants was visually
observed, and the herbicidal effect was evaluated in
accordance with a growth inhibition rate (%) of from 0
(equivalent to the non-treated area) to 100% (complete
kill) . The results are shown in Table 6.







Now, Formulation Examples of the present invention
will be described.
FORMULATION EXAMPLE 1
(1) The compound of the present invention
75 parts by weight
(2) Geropon T-77 (tradename, manufactured by Rhone-
Poulenc) 14.5 parts by weight
3) NaCl 10 parts by weight
4) Dextrin 0.5 part by weight
The above components are placed in a high-speed
mixing granulator, admixed with 2 0 wt% of water,
granulated, and dried to obtain water-dispersible
granules.
FORMULATION EXAMPLE 2
(1) Kaolin 78 parts by weight
(2) Laveline FAN (tradename, manufactured by
DAI-ICHI KOGYO SEIYAKU CO., LTD.) 2 parts by weight
(3) Sorpol 5039 (tradename, manufactured by
TOHO Chemical Industry Co., Ltd.) 5 parts by weight
(4) Carplex (tradename, manufactured by
DSL. Japan Co., Ltd.) 15 parts by weight
The mixture of the above components (1) to (4) and
the compound of the present invention are mixed in a
weight ratio of 9:1 to obtain a wettable powder.
FORMULATION EXAMPLE 3
(1) Hi-Filler No. 10 (tradename, manufactured by
Matsumura Sangyo Co., Ltd.) 33 parts by weight

(2) Sorpol 5050 (tradename, manufactured by
TOHO Chemical Industry Co., Ltd.) 3 parts by weight
(3) Sorpol 5073 (tradename, manufactured by
TOHO Chemical Industry Co., Ltd.) 4 parts by weight
(4) The compound of the present invention
60 parts by weight
The above compounds (1) to (4) are mixed to obtain a
wettable powder.
FORMULATION EXAMPLE 4
(1) The compound of the present invention
4 parts by weight
(2) Bentonite 30 parts by weight
(3) Calcium carbonate 61.5 parts by weight
(4) Toxanon GR-31A (tradename, manufactured by
Sanyo Chemical Industries Co., Ltd.)
3 parts by weight
(5) Calcium lignin sulfonate 1.5 parts by weight
Pulverized component (1) and components (2) and (3)
are preliminarily mixed, and then components (4) and (5)
and water are mixed thereto. The mixture is extruded and
granulated, followed by drying and sieving to obtain
granules.
FORMULATION EXAMPLE 5
(1) The compound of the present invention
30 parts by weight
(2) Zieclite (tradename, manufactured by
Zieclite Co., Ltd.) 60 parts by weight

(3) New Kalgen WG-1 (tradename, manufactured by
TAKEMOTO OIL & FAT CO., LTD.) 5 parts by weight
(4) New Kalgen FS-7 (tradename, manufactured by
TAKEMOTO OIL & FAT CO., LTD.) 5 parts by weight
Components (1), (2) and (3) are mixed and passed
through a pulverizer, and then component (4) is added
thereto. The mixture is kneaded and then extruded and
granulated, followed by drying and sieving to obtain
water dispersible granules.
FORMULATION EXAMPLE 6
(1) The compound of the present invention
28 parts by weight
(2) Soprophor FL (tradename, manufactured by
Rhone-Poulenc) 2 parts by weight
(3) Sorpol 33 5 (tradename, manufactured by
TOHO Chemical Industry Co., Ltd.) 1 part by weight
(4) IP solvent 1620 (tradename, manufactured by
Idemitsu Petrochemical Co., Ltd.) 32 parts by weight
(5) Ethylene glycol 6 parts by weight
(6) Water 31 parts by weight
The above components (1) to (6) are mixed and
pulverized by a wet-grinding machine (Dyno-mill) to
obtain a water-based suspension concentrate.

CLAIMS:
1. A benzoylpyrazole compound represented by the
formula (I) or its salt:

wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom
or alkyl, R3 is alkyl; cycloalkyl; haloalkyl;
alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl
which may be substituted by R8, R4 is alkyl; haloalkyl;
alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl;
or alkylsulfonyl, R5 is a hydrogen atom; alkyl; alkenyl;
alkynyl; halogen; cyano; cyanoalkyl; cyanoalkenyl;
haloalkyl; alkoxyalkyl; haloalkoxyalkyl;
amino(thiocarbonyl)alkyl which may be substituted by at
least one substituent selected from alkyl, cyano,
cyanoalkyl, (alkylthio)carbonylalkyl,
alkyl(thiocarbonyl)alkyl, -C(O)OR7 and -C(O)SR7;
thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy;
haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy;
alkoxyhaloalkoxy; haloalkoxyhaloalkoxy;
alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio;
haloalkoxyalkylthio; alkoxyhaloalkylthio;

haloalkoxyhaloalkylthio; alkylthioalkylthio;
haloalkylthioalkylthio; alkylthiohaloalkylthio;
haloalkylthiohaloalkylthio; alkylthioalkoxy;
alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl;
alkoxycarbonylalkoxy; heterocyclylalkyl; heterocyclyloxy;
heterocyclylalkoxy; heterocyclylalkoxyalkyl;
heterocyclyloxyalkyl; cycloalkyloxy; -OC(O)SR7;
-OC(0)OR7; -C(O)OR7; -C(O)SR7; -C(S)OR7; -C(S)SR7;
aminoalkyl which may be substituted by at least one
substituent selected from alkyl, cyano, cyanoalkyl,
(alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl,
-C(O)OR7 and -C(O)SR7; or 4,5-dihydroisoxazol-3-yl which
may be substituted by R9, R6 is haloalkyl; halogen;
nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl,
R7 is alkyl; haloalkyl; alkoxyalkyl; alkenyl;
haloalkenyl; alkynyl; or arylalkyl which may be
substituted by R10, and each of R8, R9 and R10 which are
independent of one another, is halogen; alkyl; or alkoxy.
2. The benzoylpyrazole compound or its salt according
to Claim 1, wherein R1 is alkyl or cycloalkyl, R2 is a
hydrogen atom or alkyl, R3 is alkyl; cycloalkyl;
haloalkyl; alkoxyalkyl; alkenyl; or arylalkyl which may
be substituted by R8, R4 is alkyl; haloalkyl; alkoxy;
halogen; nitro; cyano; alkylthio; alkylsulfinyl; or
alkylsulfonyl, R5 is a hydrogen atom; alkyl; halogen;
cyano; cyanoalkyl; haloalkyl; alkoxyalkyl;

haloalkoxyalkyl; alkoxy; haloalkoxy; alkoxyalkoxy;
haloalkoxyalkoxy; alkoxyhaloalkoxy; alkoxyalkoxyalkyl;
alkylthio; alkoxyalkylthio; haloalkoxyalkylthio;
alkylthioalkylthio; haloalkylthioalkylthio;
alkylthioalkoxy; alkylsulf onyl; alkylsulfonylalkyl;
alkoxycarbonylalkyl; alkoxycarbonylalkoxy;
heterocyclyloxy; heterocyclylalkoxy;
heterocyclylalkoxyalkyl; -OC(O)SR7; -OC(O)OR7; -C(O)OR7;
-C(O)SR7; or 4,5-dihydroisoxazol-3-yl which may be
substituted by R9, R6 is haloalkyl; halogen; nitro;
cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R7 is
alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl;
alkynyl; or arylalkyl which may be substituted by R10,
and each of R8, R9 and R10 which are independent of one
another, is halogen; alkyl; or alkoxy.
3. The benzoylpyrazole compound or its salt according
to Claim 2, wherein R1 is alkyl or cycloalkyl, R2 is a
hydrogen atom or alkyl, R3 is alkyl; cycloalkyl;
haloalkyl; alkoxyalkyl; or arylalkyl which may be
substituted by R8, R4 is alkyl; haloalkyl; alkoxy;
halogen; nitro; cyano; alkylthio; alkylsulfinyl; or
alkylsulfonyl, R5 is alkyl; haloalkyl; alkoxyalkyl;
haloalkoxyalkyl; alkoxy; haloalkoxy; alkoxyalkoxy;
haloalkoxyalkoxy; heterocyclyloxy; heterocyclylalkoxy;
heterocyclylalkoxyalkyl; -0C(O)SR7; -OC(O)OR7; -C(O)OR7;
-C(O)SR7; or 4,5-dihydroisoxazol-3-yl which may be

substituted by R9, R6 is haloalkyl; halogen; nitro;
cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R7 is
alkyl; haloalkyl; alkoxyalkyl; alkenyl; haloalkenyl;
alkynyl; or arylalkyl which may be substituted by R10,
and each of R8, R9 and R10 which are independent of one
another, is halogen; alkyl; or alkoxy.
4. The benzoylpyrazole compound or its salt according
to Claim 3, wherein R1 is alkyl, R2 is a hydrogen atom, R3
is alkyl, R4 is alkyl, R5 is alkoxy; haloalkoxy; -C(O)OR7;
or 4,5-dihydroisoxazol-3-yl, and R6 is alkylsulfonyl.
5. A benzoylpyrazole compound represented by the
formula (II-x) or its salt:

wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom
or alkyl, R4 is alkyl; haloalkyl; alkoxy; halogen; nitro;
cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R5-x is
alkyl substituted by at least 2 alkoxy; alkyl substituted
by at least 2 haloalkoxy; amino(thiocarbonyl)alkyl which
may be substituted by at least one substituent selected
from alkyl, cyano, cyanoalkyl, (alkylthio)carbonylalkyl,
alkyl(thiocarbonyl)alkyl, -C(O)OR7 and -C(O)SR7;
thiocyanatoalkyl; alkoxy substituted by at least 2
alkoxy; alkoxy substituted by at least 2 haloalkoxy;

alkoxyhaloalkoxy; haloalkoxyhaloalkoxy; alkoxyalkyl
substituted by at least 2 alkoxy; alkylthio substituted
by at least 2 alkoxy; alkylthio substituted by at least 2
haloalkoxy; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio;
alkylthioalkylthio; haloalkylthioalkylthio;
alkylthiohaloalkylthio; haloalkylthiohaloalkylthio;
alkylthioalkoxy; alkyl substituted by at least 2
alkylsulfonyl; alkyl substituted by at least 2
alkoxycarbonyl; alkoxy substituted by at least 2
alkoxycarbonyl; alkyl substituted by at least 2
heterocyclyl; alkoxy substituted by at least 2
heterocyclyl; alkyl substituted by at least 2
heterocyclylalkoxy; -OC(O)SR7; or aminoalkyl which may be
substituted by at least one substituent selected from
cyano, cyanoalkyl, (alkylthio)carbonylalkyl,
alkyl (thiocarbonyl) alkyl, -C(O)OR7 and -C(O)SR7, R6 is
haloalkyl; halogen; nitro; cyano; alkylthio;
alkylsulfinyl; or alkylsulfonyl, R7 is alkyl; haloalkyl;
alkoxyalkyl; alkenyl; haloalkenyl; alkynyl; or arylalkyl
which may-be substituted by R10, and R10 is halogen;
alkyl; or alkoxy.
6. A process for producing a benzoylpyrazole compound
represented by the formula (I) or its salt:


wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom
or alkyl, R3 is alkyl; cycloalkyl; haloalkyl;
alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl
which may be substituted by R8, R4 is alkyl; haloalkyl;
alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl;
or alkylsulfonyl, R5 is a hydrogen atom; alkyl; alkenyl;
alkynyl; halogen; cyano; cyanoalkyl; cyanoalkenyl;
haloalkyl; alkoxyalkyl; haloalkoxyalkyl;
amino(thiocarbonyl)alkyl which may be substituted by at
least one substituent selected from alkyl, cyano,
cyanoalkyl, (alkylthio)carbonylalkyl,.
alkyl(thiocarbonyl)alkyl, -C(O)OR7 and -C(O)SR7;
thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy;
haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy;
alkoxyhaloalkoxy; haloalkoxyhaloalkoxy;
alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio;
haloalkoxyalkylthio; alkoxyhaloalkylthio;
haloalkoxyhaloalkylthio; alkylthioalkylthio;
haloalkylthioalkylthio; alkylthiohaloalkylthio;
haloalkylthiohaloalkylthio; alkylthioalkoxy;

alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl;
alkoxycarbonylalkoxy; heterocyclylalkyl; heterocyclyloxy;
heterocyclylalkoxy; heterocyclylalkoxyalkyl;
heterocyclyloxyalkyl; cycloalkyloxy; -OC(O)SR7;
-OC(O)OR7; -C(O)OR7; -C(O)SR7; -C(S)OR7; -C(S)SR7;
aminoalkyl which may be substituted by at least one
substituent selected from alkyl, cyano, cyanoalkyl,
(alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl,
-C(O)OR7 and -C(O)SR7; or 4,5-dihydroisoxazol-3-yl which
may be substituted by R9, R6 is haloalkyl; halogen;
nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl,
R7 is alkyl; haloalkyl; alkoxyalkyl; alkenyl;
haloalkenyl; alkynyl; or arylalkyl which may be
substituted by R10, and each of R8, R9 and R10 which are
independent of one another, is halogen; alkyl; or alkoxy,
which comprises (1) reacting a compound represented by
the formula (II):

wherein R1, R2, R4, R5 and R6 are as defined above, with a
compound represented by the formula (III):


wherein R3 is as defined above, and Z is a leaving group,
(2) reacting a compound represented by the formula (IV-a)
and/or the formula (V-a):

wherein R , R , R4, R5 and R are as defined above, with a
compound represented by the formula (VI-a):
HS-R3-a (Vl-a)

wherein R1, R2, R4, R5 and R6 are as defined above, with a
wherein R3-a is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl;
alkoxycarbonylalkyl; alkenyl; or arylalkyl which may be
substituted by R8, or (3) reacting a compound represented
by the formula (IV-b) and/or the formula (V-b):

compound represented by the formula (VI-b):
HO-R3-b (vi-b)
wherein R3-b is alkenyl.
7. A herbicide containing the benzoylpyrazole compound
or its salt as defined in Claim 1 as an active ingredient.
8. A method for controlling undesired plants or
inhibiting their growth, which comprises applying a
herbicidally effective amount of the benzoylpyrazole
compound or its salt as defined in Claim 1 to the
undesired plants or to a place where they grow.

A benzoylpyrazole compound represented by the
formula (I) or its salt:

wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom
or alkyl, R3 is alkyl; cycloalkyl; haloalkyl;
alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl
which may be substituted by R8, R4 is alkyl; haloalkyl;
alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl;
or alkylsulfonyl, R5 is a hydrogen atom; alkyl; alkenyl;
alkynyl; halogen; cyano; cyanoalkyl; cyanoalkeny;
haloalkyl; alkoxyalkyl; haloalkoxyalkyl;
amino (thiocarbonyl) alkyl which may be substituted by at
least one substituent selected from alkyl, cyano,
cyanoalkyl, (alkylthio)carbonylalkyl,
alkyl (thiocarbonyl)alkyl, -C(O)OR7 and -C(O)SR7;
thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy;
haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy;
alkoxyhaloalkoxy; haloalkoxyhaloalkoxy;
alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio;
haloalkoxyalkylthio; alkoxyhaloalkylthio;

haloalkoxyhaloalkylthio; alkylthioalkylthio;
haloalkylthioalkylthio; alkylthiohaloalkylthio;
haloalkylthiohaloalkylthio; alkylthioalkoxy;
alkylsulfonyl; alkylsulfonylalkyl; alkoxycarbonylalkyl;
alkoxycarbonylalkoxy; heterocyclylalkyl; heterocyclyloxy;
heterocyclylalkoxy; heterocyclylalkoxyalkyl;
heterocyclyloxyalkyl; cycloalkyloxy; -OC(O)SR7;
-OC(O)OR7; -C(O)OR7; -C(O)SR7; -C(S)OR7; -C(S)SR7;
aminoalkyl which may be substituted by at least one
substituent selected from alkyl, cyano, cyanoalkyl,
(alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl,
-C(O)OR7 and -C(O)SR7; or 4,5-dihydroisoxazol-3-yl which
may be substituted by R9, R6 is haloalkyl; halogen;
nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl,
R7 is alkyl; haloalkyl; alkoxyalkyl; alkenyl;
haloalkenyl; alkynyl; or arylalkyl which may be
substituted by R10, and each of R8, R9 and R10 which are
independent of one another, is halogen; alkyl; or alkoxy.

Documents:

02128-kolnp-2008-abstract.pdf

02128-kolnp-2008-claims.pdf

02128-kolnp-2008-correspondence others.pdf

02128-kolnp-2008-description complete.pdf

02128-kolnp-2008-form 1.pdf

02128-kolnp-2008-form 3.pdf

02128-kolnp-2008-form 5.pdf

02128-kolnp-2008-gpa.pdf

02128-kolnp-2008-international publication.pdf

02128-kolnp-2008-international search report.pdf

02128-kolnp-2008-pct priority document notification.pdf

02128-kolnp-2008-pct request form.pdf

2128-KOLNP-2008-(24-07-2013)-ABSTRACT.pdf

2128-KOLNP-2008-(24-07-2013)-CLAIMS.pdf

2128-KOLNP-2008-(24-07-2013)-CORRESPONDENCE.pdf

2128-KOLNP-2008-(24-07-2013)-FORM-13.pdf

2128-KOLNP-2008-(24-07-2013)-FORM-2.pdf

2128-KOLNP-2008-(24-07-2013)-OTHERS.pdf

2128-KOLNP-2008-(24-07-2013)-PETITION UNER RULE 137.pdf

2128-KOLNP-2008-ASSIGNMENT.pdf

2128-KOLNP-2008-CORRESPONDENCE 1.1.pdf

2128-KOLNP-2008-FORM 18.pdf

2128-KOLNP-2008-FORM 3.1.pdf

abstrcat-2128-kolnp-2008.jpg


Patent Number 265495
Indian Patent Application Number 2128/KOLNP/2008
PG Journal Number 09/2015
Publication Date 27-Feb-2015
Grant Date 25-Feb-2015
Date of Filing 27-May-2008
Name of Patentee ISHIHARA SANGYO KAISHA, LTD.
Applicant Address 3-15 EDOBORI 1-CHOME NISHI-KU, OSAKA-SHI, OSAKA
Inventors:
# Inventor's Name Inventor's Address
1 SHIMOHARADA HIROSHI C/O ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO, 3-1, NISHI-SHIBUKAWA 2-CHOME,, KUSATSU-SHI,SHIGA, 5250025
2 IKEGUCHI MASAHIKO C/O ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO, 3-1, NISHI-SHIBUKAWA 2-CHOME,, KUSATSU-SHI,SHIGA, 5250025
3 KIKUGAWA HIROSHI C/O ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO, 3-1, NISHI-SHIBUKAWA 2-CHOME,, KUSATSU-SHI,SHIGA, 5250025`
4 SANO MAKIKO C/O ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO, 3-1, NISHI-SHIBUKAWA 2-CHOME,, KUSATSU-SHI,SHIGA, 5250025
5 KITAHARA YOSHINORI C/O ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO, 3-1, NISHI-SHIBUKAWA 2-CHOME,, KUSATSU-SHI,SHIGA, 5250025
6 KOMINAMI HIDEMASA C/O ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO, 3-1, NISHI-SHIBUKAWA 2-CHOME,, KUSATSU-SHI,SHIGA, 5250025
7 OKITA TATSUYA C/O ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO, 3-1, NISHI-SHIBUKAWA 2-CHOME,, KUSATSU-SHI,SHIGA, 5250025
8 TSUKAMOTO MASAMITSU C/O ISHIHARA SANGYO KAISHA, LTD., CHUO KENKYUSHO, 3-1, NISHI-SHIBUKAWA 2-CHOME,, KUSATSU-SHI,SHIGA, 5250025
PCT International Classification Number C07D 231/20
PCT International Application Number PCT/JP2006/325311
PCT International Filing date 2006-12-13
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2006-236954 2006-08-31 Japan
2 2005-362226 2005-12-15 Japan
3 2006-118304 2006-04-21 Japan