JPH0625177A - Pyrazole derivative and herbicide - Google Patents

Abstract

PURPOSE:To obtain a new compound excellent in herbicidal activity against seriously damaging weeds in paddy field, farmland, etc., with a small amount of chemical and useful as an agricultural and horticultural germicide. CONSTITUTION:A compound of formula I {R<1> is H, (substituted)1-6C alkyl, (substituted) 3-8C cycloalkyl, (substituted)2-7C alkenyl, etc.; R<2> and R<3> are H, (substituted)1-6C alkyl, (substituted)2-7C alkenyl, (substituted)2-7C alkynyl, etc.; R<4> is (substituted)1-6C alkyl, (substituted)alkenyl, (substituted)aryl, etc.; X is S(O)n, OS(O)n or NR<7>S(O)n [(n) is 0-2; R<7> is H, 1-6C alkyl, etc.]}, e.g. methyl 3-(2,6-dichlorophenylsulfamoyl)-1-(4,6-dimethylpyrimidin-2-yl)-pyrazol e-4- carboxylate. Furthermore, this compound of formula I is obtained by reacting, e.g. a compound of formula II (R<8> is H or trimethylsilyl) with a compound of formula III in the presence of a base such as triethylamine in a solvent such as methylene chloride.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel pyrazole derivative and a herbicide containing the derivative as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, a wide variety of chemicals have been put into practical use through many years of research and development of herbicides, and these herbicides have contributed to labor saving of weed control work and improvement of productivity of agricultural and horticultural crops. It was Even today, there is a demand for the development of a new drug having more excellent herbicidal properties, and as a herbicide for agriculture and horticulture, it is possible to control only target weeds selectively and at a low dose without affecting the cultivated crops. However, existing agents do not always have suitable herbicidal properties.

On the other hand, it is known that a specific compound such as a triazole sulfonamide compound has herbicidal activity, and is described, for example, in JP-A-63-22083. Further, it is known that certain compounds such as N-carbamoyltriazole compounds have herbicidal activity. For example, West German Patent No. 2132618,
U.S. Pat. No. 4,280,831, JP-A-59-39880
And Japanese Patent Laid-Open No. 2-1481.
Further, a sulfonylaminopyrazole compound is disclosed in JP-A-1-
It is described in the claims of Japanese Patent No. 268685.

[0004]

The present invention provides the formula (1):

[0005]

[Chemical 2]

[Wherein R¹Is a hydrogen atom, replaced by a
May be done C_1-6Alkyl group (a is a halogen atom, C
_1-6Alkoxy group, C_2-6Alkoxycarbonyl group, C
_2-6Alkylcarbonyloxy group, C_2-6Alkylcal
Bonylamino group, same or different C_1-6Alkyl group
An amino group substituted by 1 to 2 by C, C_2-6Archi
1 or more from a carbonyl group, a cyano group and a nitro group
Represents a substituent selected above. ), Even if replaced by a
Good C_3-8A cycloalkyl group, even if substituted by a
Good C_2-7Alkenyl group, may be substituted by a
C_2-7Alkynyl group, C optionally substituted by a
_1-6An alkylsulfonyl group, substituted by di (a
Good C_1-6Alkyl) aminocarbonyl group, di (a
Thus may be replaced by C_1-6Alkyl) aminosulfo
Nyl group, phenyl group which may be substituted by b (where b is
C_1-6Alkyl group, C_1-6Halogenoalkyl group, C_2-6
Alkenyl group, C_2-6Halogenoalkenyl group, C_2-6A
Lucinyl group, phenyl group, halogen atom, C_1-6Arco
Xy group, C_1-6Halogenoalkoxy group, C_2-6Archeni
Luoxy group, C_2-6Alkynyloxy group, phenoxy
Base, C_1-6Alkylthio group, C_1-6Halogenoalkylchi
O group, C_1-6Alkylsulfonyl group, C_1-6Halo noah
Rukylsulphonyl group, C_2-8Alkoxyalkyl group, C
_2-6Alkoxycarbonyl group, C_2-6Alkyl Carboni
Luoxy group, C_2-6Alkylcarbonylamino group, same
Or different C_1-61 to 2 depending on the alkyl group
A substituted amino group, C_2-6Alkylcarbonyl group, Ben
1 or 2 or more selected from zoyl group, cyano group and nitro group
Represents a substituent. ), B which may be replaced by b
Aromatic heterocyclic group (Aromatic heterocyclic group is thienyl group, furyl
Group, pyrazolyl group, imidazolyl group, 1,2,4-tri
Azolyl group, thiazolyl group, isothiazolyl group, 1,
3,4-thiadiazolyl group, oxazolyl group, isooxy
Sazolyl group, 1,3,4-oxadiazolyl group, pyridi
Group, pyrimidyl group, pyridazyl group, pyrazyl group, S-
It represents a triazyl group or a 1,2,4-triazyl group. )
Or an aralkyl in which the phenyl group may be substituted by b
Group (aralkyl group is C substituted by phenyl group)
_1-6Represents an alkyl group. ), R²And R³Is it
Each independently a hydrogen atom, C optionally substituted by a
_{1- 6}Alkyl group, C optionally substituted by a_2-7A
Lucenyl group, C optionally substituted by a_2-7Archi
Nyl group, C optionally substituted by a_1-6Alkylchi
O group, C optionally substituted by a_1-6Alkylsul
Finyl group, C optionally substituted by a_1-6Archi
Sulfonyl group, optionally substituted aminocarbonyl group
(Substituent is C_1-6Alkoxy group, C_2-6Alkoxycar
Bonyl group, C _2-6Alkylcarbonyloxy group, C_2-6
Alkylcarbonylamino group, same or different C
_1-6Amino substituted by 1 to 2 with an alkyl group
Base, C_2-6Selected from alkylcarbonyl and cyano groups
C) optionally substituted by a_1-6Alkyla
Minocarbonyl group, C optionally substituted by di (a
_1-6An alkyl) aminocarbonyl group, substituted by a
May be C_1-6Alkylaminosulfonyl group, di (a
C which may be replaced by_1-6Alkyl) aminosul
May be substituted by a phenyl group, a halogen atom, a
C_1-6Alkoxy group, C optionally substituted by a
_2-6An alkoxycarbonyl group, even if substituted by a
Good C_2-6Alkylcarbonyloxy group, depending on a
C that may be exchanged _2-6Alkylcarbonylamino group,
One or different C_1-61 to 2 depending on the alkyl group
A substituted amino group, C optionally substituted by a
_2-6Alkylcarbonyl group, -CR^Five= NO-R⁶Basis
(R^FiveAnd R⁶Are each independently C_{1- 6}Alkyl groups
It is C_1-6Represents an alkoxy group. ), A benzoyl group,
Cyano group, hydroxyl group, mercapto group, nitro group,
Phenyl group optionally substituted by b, substituted by b
An optionally substituted phenoxy group, optionally substituted by b
Aromatic heterocyclic group (the aromatic heterocyclic group is a thienyl group, a free
Group, pyrazolyl group, imidazolyl group, 1,2,4-tol
Lyazolyl group, thiazolyl group, isothiazolyl group, 1,
3,4-thiadiazolyl group, oxazolyl group, isooxy
Sazolyl group, 1,3,4-oxadiazolyl group, pyridi
Group, pyrimidyl group, pyridazyl group, pyrazyl group, S-
It represents a triazyl group or a 1,2,4-triazyl group. )
Or an aralkyl in which the phenyl group may be substituted by b
Group (aralkyl group is C substituted by phenyl group)
_1-6Represents an alkyl group. ), R^FourIs set by a
C that may be exchanged_1-6Alkyl group, substituted by a
May be C_2-7An alkenyl group, even if substituted by a
Good C_2-7Alkynyl group, optionally substituted by b
Aryl group (an aryl group is a phenyl group or a naphthyl group
Represent ), An aromatic heterocyclic group optionally substituted by b
(Aromatic heterocyclic groups are thienyl, furyl, pyrazolyl
Group, imidazolyl group, 1,2,4-triazolyl group, thia
Azolyl group, isothiazolyl group, 1,3,4-thiadia
Zolyl group, oxazolyl group, isoxazolyl group, oxy
Sadiazolyl group, pyridyl group, pyrimidyl group, pyridazi
Group, pyrazyl group, S-triazyl group or 1,2,4-
Represents a triazyl group. ) Or b is a phenyl group
Aralkyl groups which may be replaced (aralkyl groups are phenyl
C substituted by a group_1-6Represents an alkyl group. ) Table
X is S (O)_n, OS (O)_nOr NR⁷S (O)
_n(N represents an integer of 0 to 2 and R⁷Is a hydrogen atom, C
_1-6Alkyl group, C_2-7Alkenyl group, C_2-7Alkini
Lu group, C_1-6Alkylsulfonyl group, C_1-6Alkyla
Minocarbonyl group, C optionally substituted by di (a
_1-6An alkyl) aminocarbonyl group, substituted by a
May be C_1-6Alkylaminosulfonyl group, di (a
C which may be replaced by_1-6Alkyl) aminosul
Honyl group, C_2-6Alkoxycarbonyl group, C_2-6Al
A phenyl group is replaced by a carbonyl group or b
Aralkyl groups which may be
Replaced by C_1-6Represents an alkyl group. )]
Pyrazole derivative or a salt thereof (hereinafter referred to as the compound of the present invention
And containing one or more of them.
The present invention relates to a characteristic herbicide.

Substituents R ¹ and R of the formula (1) of the compound of the present invention
Examples of ² , R ³ , R ⁴ and X include the following. However, the compound of the present invention is not limited to this. R ¹ : hydrogen atom; methyl, ethyl, n-propyl, i-
Propyl, n-butyl, i-butyl, s-butyl, t-
Butyl, n-amyl, s-amyl, t-amyl, n-hexyl and other alkyl groups; cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and other cycloalkyl groups; vinyl, allyl, 2-butenyl, 3-butenyl, 4- Alkenyl groups such as butenyl and isopropenyl; alkynyl groups such as propargyl; alkylcarbonyl groups such as acetyl, propionyl, n-propylcarbonyl, i-propylcarbonyl, t-butylcarbonyl; methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, t-
Alkoxycarbonyl groups such as butoxycarbonyl; dimethylaminocarbonyl, diethylaminocarbonyl,
Dialkylaminocarbonyl groups such as di-n-propylaminocarbonyl and di-i-propylaminocarbonyl; alkylsulfonyl groups such as methanesulfonyl and ethanesulfonyl; aryl groups such as phenyl, 1-naphthyl, 2-naphthyl; 2-pyridyl , 3-pyridyl, 4
-Pyridyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 3-pyrazolyl, 4-pyrazolyl, 5
-Pyrazolyl, 2-imidazolyl, 4-imidazolyl,
5-imidazolyl, 3- (1,2,4-triazolyl), 5
-(1,2,4-triazolyl), 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 3-pyridazyl, 4-pyridazyl, 2-pyrazyl, s-triazyl, 3- (1,2,4
-Triazyl), 5- (1,2,4-triazyl), 6-
(1,2,4-triazyl), 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2- (1,3,4-thiadiazolyl), 3- (1 , 2,4-thiadiazolyl), 5-
(1,2,4-thiadiazolyl), 5- (1,2,3-thiadiazolyl), 2-oxazolyl, 4-oxazolyl, 5-
Oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2- (1,3,4-oxadiazolyl), 3- (1,2,4-oxadiazolyl), 5
Heterocyclic groups such as-(1,2,4-oxadiazolyl) and 5- (1,2,3-oxadiazolyl); benzyl, α-methylbenzyl, α-ethylbenzyl, α-n-propylbenzyl, α-isopropyl Aralkyl groups such as benzyl, α-n-butylbenzyl, cumyl, α, α-diethylbenzyl;

Substituents for aryl group, heterocyclic group and aralkyl group: halogen atom such as fluorine, chlorine, bromine, iodine; methoxy, ethoxy, n-propoxy, i-
Propoxy, t-butoxy and other alkoxy groups; cyano group; methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, t-
Alkoxycarbonyl group such as butoxycarbonyl; Dialkylamino group such as dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino; Nitro group; methyl, ethyl, n-propyl, i-propyl, n-butyl , Alkyl groups such as i-butyl, s-butyl, t-butyl; halogenated alkyl groups such as trifluoromethyl and trichloromethyl; halogenated alkyloxy groups such as trifluoromethoxy and difluoromethoxy; trifluoromethylthio, di Haloalkylthio group such as fluoromethylthio; Halogenated alkylsulfonyl group such as trifluoromethylsulfonyl; Alkylthio group such as methylmercapto, ethylmercapto, n-propylmercapto; Methanesulfonyl, ethanesulfonyl, etc. alkyl Ruhoniru group; methoxymethyl, alkoxyalkyl groups such as ethoxymethyl; allyl, 2
-Alkenyl groups such as butenyl, 3-butenyl, 4-butenyl and isopropenyl; alkynyl groups such as propargyl.

R ² : methyl, ethyl, n-propyl, i
-Propyl, n-butyl, i-butyl, s-butyl, t
-Butyl, n-amyl, i-amyl, s-amyl, t-
Alkyl groups such as amyl and n-hexyl; allyl, 2-
Alkenyl groups such as butenyl, 3-butenyl, 4-butenyl; alkynyl groups such as propargyl; alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy; hydrogen atoms; fluorine, chlorine, bromine, etc.
Halogen atom such as iodine; cyano group; amino group; hydroxyl group; alkylcarbonyloxy group such as acetyloxy and propionyloxy; alkylcarbonylamino group such as acetylamino and propionylamino; dialkylamino group such as dimethylamino and diethylamino; methyl Alkylthio groups such as mercapto, ethylmercapto, and n-propylmercapto; alkylsulfonyl groups such as methanesulfonyl and ethanesulfonyl; aryl groups such as phenyl group; heterocyclic groups such as 2-pyridyl and 2-pyrimidyl.

R ³ : methyl, ethyl, n-propyl, i
-Propyl, n-butyl, i-butyl, s-butyl, t
-Butyl, n-amyl, s-amyl, t-amyl, n-
Alkyl groups such as hexyl; alkenyl groups such as vinyl, allyl, 2-butenyl, 3-butenyl, 4-butenyl and isopropenyl; alkynyl groups such as propargyl; hydrogen atoms; halogen atoms such as fluorine, chlorine, bromine and iodine; Cyano group; nitro group; amino group; acetylamino,
Alkylcarbonylamino groups such as propionylamino; Dialkylamino groups such as dimethylamino and diethylamino; methylmercapto, ethylmercapto, n-
Alkylthio groups such as propylmercapto; alkylsulfonyl groups such as methanesulfonyl, ethanesulfonyl; methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, t-
Alkoxycarbonyl groups such as butoxycarbonyl; acetyl, propionyl, n-propylcarbonyl, i-
Alkylcarbonyl groups such as propylcarbonyl and t-butylcarbonyl; 2-methoxyiminoethyl groups, 2-
Alkoxyiminoalkyl groups such as ethoxyiminoethyl group; aryl groups such as phenyl, 1-naphthyl, 2-naphthyl; 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furyl, 3 -Furyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3- (1,2,4-triazolyl), 5- (1,2,4
-Triazolyl), 2-pyrimidyl, 4-pyrimidyl,
5-pyrimidyl, 3-pyridazyl, 4-pyridazyl, 2
-Pyrazyl, s-triazyl, 3- (1,2,4-triazyl), 5- (1,2,4-triazyl), 6- (1,2,4-triazyl), 2-thiazolyl, 4-thiazolyl , 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl,
5-isothiazolyl, 2- (1,3,4-thiadiazolyl), 3- (1,2,4-thiadiazolyl), 5- (1,2,4
-Thiadiazolyl), 5- (1,2,3-thiadiazolyl), 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2- (1,3,4-oxadiazolyl) ), 3- (1,2,4-oxadiazolyl), 5-
Heterocyclic groups such as (1,2,4-oxadiazolyl) and 5- (1,2,3-oxadiazolyl); benzyl, α-methylbenzyl, α-ethylbenzyl, α-n-propylbenzyl, α-isopropylbenzyl , Aralkyl groups such as α-n-butylbenzyl, cumyl, α, α-diethylbenzyl;

Substituents for aryl group, heterocyclic group and aralkyl group: halogen atom such as fluorine, chlorine, bromine and iodine; methoxy, ethoxy, n-propoxy, i-
Alkoxy groups such as propoxy and t-butoxy; cyano groups; alkenyloxy groups such as allyloxy, 2-butenyloxy, 3-butenyloxy and 4-butenyloxy; alkynyloxy groups such as propargyloxy; methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl , Alkoxycarbonyl groups such as i-propoxycarbonyl and t-butoxycarbonyl; alkylcarbonyloxy groups such as acetyloxy and propionyloxy; alkylcarbonylamino groups such as acetylamino and propionylamino; dimethylamino, diethylamino, di-n-propyl Dialkylamino groups such as amino and di-i-propylamino; acetyl, propionyl, n-propylcarbonyl, i-propylcarbonyl, t-butylcarbonyl Alkylcarbonyl groups such as; nitro groups; alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl; halogens such as trifluoromethyl, trichloromethyl, etc. Alkyl groups; halogenated alkyloxy groups such as trifluoromethoxy and difluoromethoxy; halogenated alkylthio groups such as trifluoromethylthio and difluoromethylthio; halogenated alkylsulfonyl groups such as trifluoromethylsulfonyl; methylmercapto, ethylmercapto , Alkylthio groups such as n-propylmercapto; alkylsulfonyl groups such as methanesulfonyl and ethanesulfonyl; alkoxyalkyl groups such as methoxymethyl and ethoxymethyl; allyl, 2
-Alkenyl groups such as butenyl, 3-butenyl, 4-butenyl and isopropenyl; alkynyl groups such as propargyl; 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3, Halogenated alkenyl group such as 3-trichloroallyl; alkynyl group such as propargyl; benzoyl group; phenyl group; phenoxy group.

R ⁴ : methyl, ethyl, n-propyl, i
-Propyl, n-butyl, i-butyl, s-butyl, t
-Butyl, n-amyl, s-amyl, t-amyl, n-
Alkyl groups such as hexyl; vinyl, allyl, 2-butenyl, 3-butenyl, 4-butenyl, isopropenyl,
Alkenyl groups such as geranyl and citronellyl; alkynyl groups such as propargyl; phenyl, 1-naphthyl, 2-
Aryl groups such as naphthyl; 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-
Furyl, 3-furyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3- (1,2,4-triazolyl), 5- (1,2,4 -Triazolyl), 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 3-pyridazyl, 4-pyridazyl, 2-pyrazyl, s-triazyl,
3- (1,2,4-triazyl), 5- (1,2,4-triazyl), 6- (1,2,4-triazyl), 2-thiazolyl,
4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-
(1,3,4-thiadiazolyl), 3- (1,2,4-thiadiazolyl), 5- (1,2,4-thiadiazolyl), 5- (1,
2,3-thiadiazolyl), 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl,
4-isoxazolyl, 5-isoxazolyl, 2-
(1,3,4-oxadiazolyl), 3- (1,2,4-oxadiazolyl), 5- (1,2,4-oxadiazolyl), 5
Heterocyclic groups such as-(1,2,3-oxadiazolyl); benzyl, α-methylbenzyl, α-ethylbenzyl, α-
n-propylbenzyl, α-isopropylbenzyl, α
An aralkyl group such as -n-butylbenzyl, cumyl, α, α-diethylbenzyl;

Substituents for alkyl, alkenyl and alkynyl groups: halogen atoms such as fluorine, chlorine, bromine and iodine; methoxy, ethoxy, n-propoxy, i
-Alkoxy groups such as propoxy and t-butoxy; cyano groups; methoxycarbonyl, ethoxycarbonyl, n-
Propoxycarbonyl, i-propoxycarbonyl, t
An alkoxycarbonyl group such as butoxycarbonyl;
Alkylcarbonyloxy groups such as acetyloxy and propionyloxy; alkylcarbonylamino groups such as acetylamino and propionylamino; dimethylamino, diethylamino, di-n-propylamino, di-i
-Dialkylamino group such as propylamino; alkylcarbonyl group such as acetyl, propionyl, n-propylcarbonyl, i-propylcarbonyl, t-butylcarbonyl; nitro group;

Substituents for aryl group, heterocyclic group and aralkyl group: halogen atom such as fluorine, chlorine, bromine, iodine; methoxy, ethoxy, n-propoxy, i-
Alkoxy groups such as propoxy and t-butoxy; cyano groups; alkenyloxy groups such as allyloxy, 2-butenyloxy, 3-butenyloxy and 4-butenyloxy; alkynyloxy groups such as propargyloxy; methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl , Alkoxycarbonyl groups such as i-propoxycarbonyl and t-butoxycarbonyl; alkylcarbonyloxy groups such as acetyloxy and propionyloxy; alkylcarbonylamino groups such as acetylamino and propionylamino; dimethylamino, diethylamino, di-n-propyl Dialkylamino groups such as amino and di-i-propylamino; acetyl, propionyl, n-propylcarbonyl, i-propylcarbonyl, t-butylcarbonyl Alkylcarbonyl groups such as; nitro groups; alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl; halogens such as trifluoromethyl, trichloromethyl, etc. Alkyl groups; halogenated alkyloxy groups such as trifluoromethoxy and difluoromethoxy; halogenated alkylthio groups such as trifluoromethylthio and difluoromethylthio; halogenated alkylsulfonyl groups such as trifluoromethylsulfonyl; methylmercapto, ethylmercapto , Alkylthio groups such as n-propylmercapto; alkylsulfonyl groups such as methanesulfonyl and ethanesulfonyl; alkoxyalkyl groups such as methoxymethyl and ethoxymethyl; allyl, 2
-Alkenyl groups such as butenyl, 3-butenyl, 4-butenyl and isopropenyl; alkynyl groups such as propargyl; 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3, Halogenated alkenyl group such as 3-trichloroallyl; alkynyl group such as propargyl; benzoyl group; phenyl group; phenoxy group.

X: S, SO, SO ₂ , OSO ₂ , NHS
O ₂ .

The compound of the present invention has excellent selectivity for crops such as rice, corn, soybean, wheat, barley, sorghum and cotton, and has a low dose and is excellent for highly damaging weeds in paddy fields and fields. Shows herbicidal activity. The compound of the present invention can be easily produced by the following synthetic method.

[0017]

[Chemical 3]

[0018]

[Chemical 4]

[Wherein R¹, R², R³, R^Four, R⁷,
X and n have the same meanings as described above, and R ⁸Is a hydrogen atom or
Represents a trimethylsilyl group, R⁹Is R¹Similar meaning to
Represents However, R⁹Excludes hydrogen atoms. Hal is a halogen
Represents a hydrogen atom, Y is a halogen atom, a methanesulfonyl group
Or a benzylsulfonyl group, Z is a methyl group or a methyl group.
2-pyridyl, 4-pi, which may be substituted with a toxy group
Lysyl, 2-pyrimidyl, 4-pyrimidyl or s-tri
Represents an azyl group. ]

The reactions represented by (A) and (F) are usually carried out in a solvent in the presence of a base in an amount of 0.9 to 2.0 times that of the formula (3). The solvent may be inert to the reaction, and halogenated hydrocarbons such as chloroform, methylene chloride, carbon tetrachloride, dichloroethane and trichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, diethyl ether. , Ethers such as tetrahydrofuran, acetone, ketones such as methyl ethyl ketone, pyridine, triethylamine, organic bases such as N, N-dimethylaniline, ethyl acetate, esters such as methyl acetate, acetonitrile, N, N- Examples thereof include dimethylformamide and dimethylsulfoxide.

Examples of the base include inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate and sodium hydride, pyridine, triethylamine, N, N-dimethylaniline, N, Examples thereof include organic salts such as N-diethylaniline and 4-N, N-dimethylpyridine. The reaction temperature may be from -50 ° C to 200 ° C, but is preferably from the freezing point to the boiling point of the solvent in operation.

Although the reaction time depends on the reaction conditions, it is usually completed in 5 minutes to 100 hours. The reaction represented by (B) is usually performed in a solvent in the presence of a 1.0 to 2.0-fold molar amount of a base with respect to the formula (4). The solvent may be inert to the reaction, and halogenated hydrocarbons such as chloroform, methylene chloride, carbon tetrachloride, dichloroethane and trichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, diethyl ether. , Ethers such as tetrahydrofuran, acetone, ketones such as methyl ethyl ketone, pyridine, triethylamine, organic bases such as N, N-dimethylaniline, ethyl acetate, esters such as methyl acetate, acetonitrile, N, N- Examples thereof include dimethylformamide and dimethylsulfoxide.

As the base, inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydride, pyridine, triethylamine, N, N-dimethylaniline, N, Examples thereof include organic salts such as N-diethylaniline and 4-N, N-dimethylpyridine. The reaction temperature may be from -50 ° C to 200 ° C, but is preferably from the freezing point to the boiling point of the solvent in operation.

The reaction time depends on the reaction conditions, but is usually completed in 5 minutes to 100 hours. The reactions represented by (C), (G), and (H) are usually performed in a solvent at 0.9 with respect to the formula (7).
It is carried out in the presence of ˜2.0-fold molar base. Any solvent may be used as long as it is inert to the reaction, and halogenated hydrocarbons such as chloroform, methylene chloride, carbon tetrachloride, dichloroethane and trichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene. , Ethers such as diethyl ether, tetrahydrofuran, acetone, ketones such as methyl ethyl ketone, pyridine, triethylamine, N, N-
Examples thereof include organic bases such as dimethylaniline, ethyl acetate, esters such as methyl acetate, acetonitrile, N, N-dimethylformamide, dimethyl sulfoxide and the like.

As the base, inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, pyridine, triethylamine, N, N-dimethylaniline, N, Examples thereof include organic salts such as N-diethylaniline and 4-N, N-dimethylpyridine. The reaction temperature may be from -50 ° C to 200 ° C, but is preferably from the freezing point to the boiling point of the solvent in operation.

The reaction time depends on the reaction conditions, but is usually completed in 5 minutes to 100 hours. The reaction represented by (D) is usually carried out in a solvent in the presence of a base in an amount of 2.0 to 4.0 times that of the formula (3). Solvents that may be used may be inert to the reaction, halogenated hydrocarbons such as chloroform, methylene chloride, carbon tetrachloride, dichloroethane, trichloroethane, aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, Diethyl ether, ethers such as tetrahydrofuran, acetone, ketones such as methyl ethyl ketone, pyridine,
Organic bases such as triethylamine, N, N-dimethylaniline, esters such as ethyl acetate and methyl acetate,
Acetonitrile, N, N-dimethylformamide, dimethylsulfoxide and the like can be mentioned.

As the base, inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, pyridine, triethylamine, N, N-dimethylaniline, N, Examples thereof include organic salts such as N-diethylaniline and 4-N, N-dimethylpyridine. The reaction temperature may be from -50 ° C to 200 ° C, but is preferably from the freezing point to the boiling point of the solvent in operation.

The reaction time depends on the reaction conditions, but is usually completed in 5 minutes to 100 hours. The hydrolysis reactions represented by (E), (G) and (H) are usually carried out in a solvent in the formula (1).
0), equations (13) and (16) for 1.0-4.
It is carried out in the presence of 0-fold molar base. The solvent that can be used is water or a mixture of water and an organic solvent, and as the organic solvent, methanol, alcohols such as ethanol, acetone, ketones such as methyl ethyl ketone,
Pyridine, triethylamine, organic bases such as N, N-dimethylaniline, acetonitrile, N, N-dimethylformamide, dimethylsulfoxide and the like can be mentioned.

As the base, inorganic salts such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydride, pyridine, triethylamine, N, N-dimethylaniline, N, Examples thereof include organic salts such as N-diethylaniline and 4-N, N-dimethylpyridine. The reaction temperature may be from -50 ° C to 200 ° C, but is preferably from the freezing point to the boiling point of the solvent in operation.

Although the reaction time depends on the reaction conditions, it is usually completed in 5 minutes to 100 hours. After the completion of the reaction, a usual post-treatment is carried out, and if necessary, it can be purified by recrystallization, column chromatography or the like. Examples of the pyrazole sulfonyl chloride-based compound represented by the formula (3) and the compound represented by the formula (16) include Acta. Chemica Scandinavian (Acta. Chem. Scand.), 24 ,
p. 1191 (1970), Hemitsche Berichte (C
hem. Ber. ), 95, 2861 (1962) or the method described in JP-A-61-112072.

The pyrazole compound represented by the formula (7) is, for example, Alkyv for Chemi (Arkiv).
for Kemi), 8 , 52, p. 523 (195
5) or Acta Hemica Scandinavian (Acta.
Chem. Scand. ), 16 , p. 2395 (19
It can be synthesized by the method described in 62).

[0032]

EXAMPLES Next, the production of the compound of the present invention will be specifically described with reference to examples. Example 1 Methyl 3- (2,6-dichlorophenylsulfamoyl) -1- (4,6-dimethylpyrimidine-
Preparation of 2-yl) -pyrazole-4-carboxylate (Compound No. 1) 2,6-dichloroaniline (1.2 g) and 4-dimethylaminopyridine (0.
1 g) to a stirred solution of methyl 3-chlorosulfonyl-1-
2.6 g of (4,6-dimethylpyrimidin-2-yl) -pyrazole-4-carboxylate were added in small portions.
After 12 hours at 25 ° C, the reaction solution was heated to 70 ° C and stirring was continued for another 3 hours. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure, 100 ml of water was added, and then 200 ml of a saturated aqueous sodium carbonate solution and 200 ml of chloroform were added. The generated crystals and the aqueous layer were separated, acidified with concentrated hydrochloric acid, and the generated crystals were collected by filtration. The obtained crystals were washed with diethyl ether and dried to give the title object compound (2.2 g). Melting point 275-278 ° C

Example 2 Production of methyl 3- (2,6-dichlorophenylsulfamoyl) -1- (4,6-dimethoxypyrimidin-2-yl) -pyrazole-4-carboxylate (Compound No. 17) 5 g of the compound obtained in Example 1 was converted into ethyl alcohol 10
It was dissolved in 0 ml and 100 ml of water, 3 g of sodium hydroxide was added, and stirring was continued for 5 hours under reflux conditions. After completion of the reaction, most of the ethyl alcohol was distilled off from the reaction solution under reduced pressure, and water 1
After adding 00 ml, it was acidified with concentrated hydrochloric acid and the resulting crystals were collected by filtration. The obtained crystals were washed with diethyl ether and dried, then added to thionyl chloride (50 ml) and the mixture was stirred under reflux for 5 hours. After completion of the reaction, the solvent was completely distilled off under reduced pressure, dried methyl alcohol was added, and stirring was continued for 1 hour under reflux conditions. After completion of the reaction, most of the methyl alcohol was distilled off from the reaction solution under reduced pressure, and chloroform 3
00 ml and 100 ml of water were added. The chloroform layer was separated and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to remove methyl 3- (2,6-dichlorophenylsulfamoyl) -1-H-pyrazole-4-carboxylate.2.
6 g was obtained. Melting point 227-230 [deg.] C. 0.6 g of the obtained methyl 3- (2,6-dichlorophenylsulfamoyl) -1-H-pyrazole-4-carboxylate was dissolved in 20 ml of dry dimethylformamide and sodium hydride. 15 g was added at room temperature. After stirring at room temperature for 30 minutes, 0.38 g of 4,6-dimethoxy-2-methanesulfonylpyrimidine was added and the reaction solution was added to 7
Heat to 0 ° C. and continue stirring for an additional 3 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure to remove the solvent, and 200 ml of chloroform was added to the reaction solution. The solution was washed with dilute hydrochloric acid, the chloroform layer was removed, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The crystals formed by adding 10 ml of methyl alcohol were collected by filtration and dried to obtain 0.7 g of the title compound. Melting point 258-2
61 ° C

The compounds of the present invention obtained in the same manner as in Examples 1 and 2 are shown in Tables 1 to 5. [Table 1]

[0035]

[Chemical 5]

─────────────────────────── Compound R ² R ³ R ⁴ Melting point number (℃) ────── ───────────────────── 1 H CO ₂ Me 2,6-Cl ₂ -Ph 275-278 2 H CO ₂ Et 2,6-Cl ₂ -Ph 241-242 3 H CO ₂ i-Pr 2,6-Cl ₂ -Ph 241-244 4 H CN 2,6-Cl ₂ -Ph 250-252 5 H CN 2,6-F ₂ -Ph 269-271 6 H CONMe ₂ 2,6-Cl ₂ -Ph 252-255 7 H CONHMe 2,6-Cl ₂ -Ph 254-257 8 H CONH ₂ 2,6-Cl ₂ -Ph 279-280 9 H CONHNHCOMe 2,6- Cl ₂ -Ph 177-180 10 HQ ₁ 2,6-Cl ₂ -Ph 272-275 11 Me CO ₂ Et 2,6-Cl ₂ -Ph 227-230 12 Me COMe 2,6-Cl ₂ -Ph 235- 238 13 Me C (Me) = NOMe 2,6-Cl ₂ -Ph 220-223 14 HH 2,6-Cl ₂ -Ph 256-259 ────────────────── ─────────

[Table 2]

[0038]

[Chemical 6]

─────────────────────────── Compound R ² R ³ R ⁴ Melting point number (℃) ────── ───────────────────── 15 H CO ₂ Me 2,6-Cl ₂ -Ph 227-230 16 Me CO ₂ Et 2,6-Cl ₂ -Ph 218-221 ───────────────────────────

[Table 3]

[0041]

[Chemical 7]

─────────────────────────── Compound R ² R ³ R ⁴ Melting point number (℃) ────── ───────────────────── 17 H CO ₂ Me 2,6-Cl ₂ -Ph 258-261 18 Me CO ₂ Et 2,6-Cl ₂ -Ph 253-255 ───────────────────────────

[Table 4]

[0044]

[Chemical 8]

─────────────────────────── Compound R ² R ³ R ⁴ Melting point number (℃) ────── ───────────────────── 19 H CN 2,6-Cl ₂ -Ph 262-265 20 HH 2,6-Cl ₂ -Ph 277-280 ── ─────────────────────────

[Table 5]

[0047]

[Chemical 9]

──────────────────────────── Compound R ² R ³ X R ⁴ Melting point number (℃) ───── ────────────────────── 21 H CO ₂ Et CH ₂ S Ph 65-67 22 H CO ₂ Et CH ₂ SO ₂ Ph 77-80 23 HH CH ₂ S Ph oily 24 HH CH ₂ SO ₂ Ph oily ───────────────────────────

Next, the compounds synthesized according to the above Examples are shown in Table 6 including the above Examples. However, the present invention is not limited to these. [Table 6]

[0050]

[Chemical 10]

─────────────────────────── R ¹ R ² R ³ X R ⁴ ──────────── ──────────────── 4,6-Me ₂ -Q ₂ H CO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ H CO ₂ Et NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ H CO ₂ i-Pr NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ H COMe NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ H NO ₂ NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ H SO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ H CN NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ HH NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ HQ ₁ NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₂ H CO ₂ Me NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₂ H CO ₂ Et NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₂ H CO ₂ i-Pr NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₂ H COMe NHSO ₂ 2 , 6-F ₂ -Ph 4,6-Me ₂ -Q ₂ H NO ₂ NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₂ H SO ₂ Me NHSO ₂ 2,6-F ₂ -Ph ───────────────────────────

[Continued Table 6] ─────────────────────────── R ¹ R ² R ³ X R ⁴ ───── ────────────────────── 4,6-Me ₂ -Q ₂ H CN NHSO ₂ 2,6-F ₂ -Ph 4,6-Me _2- Q ₂ HH NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₂ HQ ₁ NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₂ H CO ₂ Me NHSO ₂ 2 , 6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₂ H CO ₂ Et NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₂ H CO ₂ i-Pr NHSO ₂ 2,6 -Cl ₂ -Ph 4,6-OMe ₂ -Q ₂ H COMe NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₂ H NO ₂ NHSO ₂ 2,6-Cl ₂ -Ph 4, 6-OMe ₂ -Q ₂ H SO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₂ H CN NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₂ HH NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₂ HQ ₁ NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₂ H CO ₂ Me NHSO ₂ 2, 6-F ₂ -Ph 4,6-OMe ₂ -Q ₂ H CO ₂ Et NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₂ H CO ₂ i-Pr NHSO ₂ 2,6- F ₂ -Ph 4,6-OMe ₂ -Q ₂ H COMe NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₂ H NO ₂ NHSO ₂ 2,6-F ₂ -Ph 4,6 -OMe ₂ -Q ₂ H SO ₂ Me NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe _2- Q ₂ H CN NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₂ HH NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₂ HQ ₁ NHSO ₂ 2,6 -F ₂ -Ph 4-OMe-6-Me-Q ₂ H CO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₂ H CO ₂ Et NHSO ₂ 2,6-Cl ₂ -Ph ───────────────────────────

[Continued Table 6] ─────────────────────────── R ¹ R ² R ³ X R ⁴ ───── ────────────────────── 4-OMe-6-Me-Q ₂ H CO ₂ i-Pr NHSO ₂ 2,6-Cl ₂ -Ph 4- OMe-6-Me-Q ₂ H COMe NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₂ H NO ₂ NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me -Q ₂ H SO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₂ H CN NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₂ HH NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₂ HQ ₁ NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₂ H CO ₂ Me NHSO ₂ 2, 6-F ₂ -Ph 4-OMe-6-Me-Q ₂ H CO ₂ Et NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₂ H CO ₂ i-Pr NHSO ₂ 2, 6-F ₂ -Ph 4-OMe-6-Me-Q ₂ H COMe NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₂ H NO ₂ NHSO ₂ 2,6-F _2- Ph 4-OMe-6-Me-Q ₂ H SO ₂ Me NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₂ H CN NHSO ₂ 2,6-F ₂ -Ph 4-OMe -6-Me-Q ₂ HH NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₂ HQ ₁ NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₃ H CO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₃ H CO ₂ Et NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me _2- Q ₃ H CO ₂ i-Pr NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₃ H COMe NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₃ H NO ₂ NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₃ H SO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₃ H CN NHSO ₂ 2,6 -Cl ₂ -Ph ────────────────────────────

[Continued Table 6] ─────────────────────────── R ¹ R ² R ³ X R ⁴ ───── ────────────────────── 4,6-Me ₂ -Q ₃ HH NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₃ HQ ₁ NHSO ₂ 2,6-Cl ₂ -Ph 4,6-Me ₂ -Q ₃ H CO ₂ Me NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₃ H CO ₂ Et NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₃ H CO ₂ i-Pr NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₃ H COMe NHSO ₂ 2,6 -F ₂ -Ph 4,6-Me ₂ -Q ₃ H NO ₂ NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₃ H SO ₂ Me NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₃ H CN NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₃ HH NHSO ₂ 2,6-F ₂ -Ph 4,6-Me ₂ -Q ₃ HQ ₁ NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₃ H CO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₃ H CO ₂ Et NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₃ H CO ₂ i-Pr NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₃ H COMe NHSO ₂ 2,6- Cl ₂ -Ph 4,6-OMe ₂ -Q ₃ H NO ₂ NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₃ H SO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4 , 6-OMe ₂ -Q ₃ H CN NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₃ HH N HSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₃ HQ ₁ NHSO ₂ 2,6-Cl ₂ -Ph 4,6-OMe ₂ -Q ₃ H CO ₂ Me NHSO ₂ 2,6- F ₂ -Ph 4,6-OMe ₂ -Q ₃ H CO ₂ Et NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₃ H CO ₂ i-Pr NHSO ₂ 2,6-F ₂ -Ph ───────────────────────────

[Continued Table 6] ─────────────────────────── R ¹ R ² R ³ X R ⁴ ───── ────────────────────── 4,6-OMe ₂ -Q ₃ H COMe NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe _2- Q ₃ H NO ₂ NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₃ H SO ₂ Me NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₃ H CN NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₃ HH NHSO ₂ 2,6-F ₂ -Ph 4,6-OMe ₂ -Q ₃ HQ ₁ NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₃ H CO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₃ H CO ₂ Et NHSO ₂ 2,6-Cl ₂ -Ph 4- OMe-6-Me-Q ₃ H CO ₂ i-Pr NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₃ H COMe NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe- 6-Me-Q ₃ H NO ₂ NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₃ H SO ₂ Me NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me -Q ₃ H CN NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₃ HH NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₃ HQ ₁ NHSO ₂ 2,6-Cl ₂ -Ph 4-OMe-6-Me-Q ₃ H CO ₂ Me NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₃ H CO ₂ Et NHSO ₂ 2, 6-F ₂ -Ph 4-OMe-6-Me-Q ₃ H CO ₂ i-Pr NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6- Me-Q ₃ H COMe NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₃ H NO ₂ NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₃ H SO ₂ Me NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₃ H CN NHSO ₂ 2,6-F ₂ -Ph 4-OMe-6-Me-Q ₃ HH NHSO ₂ 2, 6-F ₂ -Ph ────────────────────────────

[Continued Table 6] ─────────────────────────── R ¹ R ² R ³ X R ⁴ ───── ────────────────────── 4-OMe-6-Me-Q ₃ HQ ₁ NHSO ₂ 2,6-F ₂ -Ph CONEt ₂ H CO ₂ Me SO ₂ 2,6-Me ₂ -Ph CONEt ₂ H CO ₂ Et SO ₂ 2,6-Me ₂ -Ph CONEt ₂ H COMe SO ₂ 2,6-Me ₂ -Ph CONEt ₂ H NO ₂ SO ₂ 2,6 -Me ₂ -Ph CONEt ₂ H CN SO ₂ 2,6-Me ₂ -Ph CONEt ₂ H SO ₂ Me SO ₂ 2,6-Me ₂ -Ph CONEt ₂ H CO ₂ Me OSO ₂ 2,6-Me _2- Ph CONEt ₂ H CO ₂ Et OSO ₂ 2,6-Me ₂ -Ph CONEt ₂ H COMe OSO ₂ 2,6-Me ₂ -Ph CONEt ₂ H NO ₂ OSO ₂ 2,6-Me ₂ -Ph CONEt ₂ H CN OSO ₂ 2,6-Me ₂ -Ph CONEt ₂ H SO ₂ Me OSO ₂ 2,6-Me ₂ -Ph CONEt ₂ H CO ₂ Me SO ₂ CH ₂ Ph CONEt ₂ H CO ₂ Et SO ₂ CH ₂ Ph CONEt ₂ H COMe SO ₂ CH ₂ Ph CONEt ₂ H NO ₂ SO ₂ CH ₂ Ph CONEt ₂ H CN SO ₂ CH ₂ Ph CONEt ₂ H SO ₂ Me SO ₂ CH ₂ Ph CONEt ₂ H CO ₂ Me SO ₂ 2,4,6 -Me ₃ -Ph CONEt ₂ H CO ₂ Et SO ₂ 2,4,6-Me ₃ -Ph CONEt ₂ H COMe SO ₂ 2,4,6-Me ₃ -Ph CONEt ₂ H NO ₂ SO ₂ 2,4, 6- Me ₃ -Ph ───────────────────────────

[Continued Table 6] ─────────────────────────── R ¹ R ² R ³ X R ⁴ ───── ────────────────────── CONEt ₂ H CN SO ₂ 2,4,6-Me ₃ -Ph CONEt ₂ H SO ₂ Me SO ₂ 2,4, 6-Me ₃ -Ph CONEt ₂ H CO ₂ Me OSO ₂ 2,4,6-Me ₃ -Ph CONEt ₂ H CO ₂ Et OSO ₂ 2,4,6-Me ₃ -Ph CONEt ₂ H COMe OSO ₂ 2, 4,6-Me ₃ -Ph CONEt ₂ H NO ₂ OSO ₂ 2,4,6-Me ₃ -Ph CONEt ₂ H CN OSO ₂ 2,4,6-Me ₃ -Ph CONEt ₂ H SO ₂ Me OSO ₂ 2 , 4,6-Me ₃ -Ph ───────────────────────────

When the compound of the present invention is used as a herbicide for agricultural and horticultural use, it is generally a suitable carrier, for example, solid carrier such as clay, talc, bentonite, diatomaceous earth or water, alcohols (methanol, ethanol, etc.), aromatic. Hydrocarbons (benzene, toluene, xylene, etc.),
It can be applied by mixing with a liquid carrier such as chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetate etc.), acid amides (dimethylformamide etc.), and if desired, an emulsifier, a dispersant, a suspension Add turbidity agents, penetrants, spreading agents, stabilizers, etc. to prepare liquids, emulsions, wettable powders, powders, granules,
It can be put to practical use in any dosage form such as a flowable agent. Further, if necessary, it may be mixed and applied with other types of herbicides, various insecticides, fungicides, plant growth regulators, synergists and the like at the time of formulation or spraying. The types of herbicides to be mixed include, for example, Farm Chemicals Handbook (Fa
RM Chemicals Handbook) 1990 compounds. To name a few, atrazine, cyanadine, alachlor metolachlor,
Examples include EPTC, 2,4-D, butyrate, dicamba, bromoxynil and tridifane. The amount of application varies depending on the application scene, application time, application method, cultivated crops, etc., but in general, an appropriate amount of the active ingredient is about 0.001 to 10 kg per hectare.

Next, formulation examples of the herbicide containing the compound of the present invention as an active ingredient will be shown, but the invention is not limited thereto. In the following formulation examples, "part" means part by weight. [Formulation Example 1] Wettable powder Compound No. 1 of the present invention 1 ──────── 60 parts Diklite PFP ────────────── 33 parts (Kaolin-based clay: product name of Sikhlite Industry Co., Ltd.) ) Solpol 5039 ─────────── 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex (anti-caking agent) ───── 2 parts (White carbon: Shionogi Pharmaceutical Co., Ltd. trade name) The above is uniformly mixed and pulverized to obtain a wettable powder.

[Formulation Example 2] Emulsion Compound No. 1 of the present invention 1 ──────── 1.5 parts Xylene ────────────── 78.5 parts N, N-Dimethylformamide ───── 15 parts Solball 2680 ─────────── 5 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Mix uniformly to make an emulsion.

[Formulation Example 3] Flowable agent Compound No. 1 of the present invention 1 ──────── 40 parts Agrisol B-710 ───────── 10 parts (Nonionic surfactant: Kao Corporation) Product name: Lunox 1000C ─────────── 0.5 part (Anionic surfactant: Toho Chemical Industry Co., Ltd. product name) 1% Rhodopol water ─────────── 20 parts (thickener: Trade name of Lorne Boulan) Water ───────────────── 29.5 parts The above ingredients are mixed uniformly to make a flowable agent.

[Formulation Example 4] Granule Compound No. 1 of the present invention 1 ────── 1 part Bentonite ────── 55 parts Tark ────── 44 parts The above components are uniformly mixed and ground. After that, a small amount of water is added, and the mixture is kneaded with stirring, granulated by an extrusion type granulator, and dried to obtain granules.

The compounds of the present invention can be used for controlling various weeds in non-agricultural fields such as athletic fields, open spaces and route ends, as well as agricultural and horticultural fields such as upland fields, paddy fields and orchards. Although there are differences depending on the application scene, application time, target grass species, etc., generally 0.001 to 5 per hectare
It is suitable to sprinkle it to about kg. Next, the herbicidal effect of the compound of the present invention will be specifically described with reference to test examples.

[Test Example-1] Herbicidal effect test by soil treatment: A sterilized diluvial soil was put in a plastic box having a length of 15 cm, a width of 22 cm, and a depth of 6 cm.
Pepper, rice, corn, wheat, soybean, and cotton were mixed and sown, and after covering the soil for about 1.5 cm, the active ingredient amount was uniformly sprayed on the soil surface. The chemical solution for spraying was prepared by diluting a wettable powder appropriately adjusted according to the above formulation example with water and spraying it with a small spray. Chemical spray 3
After a week, the herbicidal effect on crops and various weeds was visually observed and investigated according to the following criteria. The results are shown in Table 7. Criteria 5: Herbicide rate 90% or more (almost complete death) 4: Herbicide rate 70-90% 3: Herbicide rate 40-70% 2: Herbicide rate 20-40% 1: Herbicide rate 5-20% 0: Herbicide rate 5% or less (almost ineffective)

[Test Example 2] Herbicidal effect test by foliar treatment: A sterilized diluvial soil was placed in a plastic box having a length of 15 cm, a width of 22 cm, and a depth of 6 cm, and then the periwinkle, the oyster bark,
Seeds of dog pepper, rice, corn, wheat, soybean, cotton, and beet were sowed in spots, respectively.
5 cm of soil was covered. When various plants reached the 2-3 leaf stage, the active ingredients were sprayed evenly on the foliage so that the amount of the active ingredient became a predetermined ratio. The chemical solution for spraying was appropriately adjusted according to the above-mentioned formulation example and the like, and the wettable powder was diluted with water and sprayed on the entire foliage of various plants with a small spray. Three weeks after spraying the chemical solution, the herbicidal effect on crops and various weeds was visually observed and investigated according to the criteria of Test Example 1. The results are shown in Table 8.

The symbols in the table represent the following. A: Acacia catechu, B: Barnacles, C: Pepper, a: Rice,
b: corn, c: wheat, d: soybean, e: cotton, f: beet

[Table 7] Herbicidal effect test by soil treatment ────────────────────────── Compound Amount A B C a b c d No. e (kg / ha) ────────────────────────── 1 0.63 5 5 5 0 0 0 0 0 0 2 0.63 5 5 5 5 0 0 0 0 0 4 2.5 5 5 5 5 0 0 0 0 0 0 14 0.63 5 5 5 1 1 0 0 0 0 0 17 0.63 5 5 5 5 0 0 0 0 0 0 ──────────────── ──────────

[Table 8] Herbicidal effect test by foliar treatment ──────────────────────────── Compound Amount A B C a b cdef number (kg / ha) ──────────────────────────── 1 0.63 5 5 5 0 0 0 0 4 4 4 2 0.63 5 5 3 0 0 0 3 3 0 1 4 2.5 5 5 5 5 0 0 0 0 0 0 4 6 2.5 5 5 5 5 0 0 0 4 3 3 1 14 0.63 4 4 5 0 0 0 0 1 1 0 0 17 2.5 5 5 5 5 0 0 0 3 13 ─────────────────────────────

Front page continued (72) Inventor Namaki Tsutomu 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama Nissan Biochemical Research Institute, Inc. (72) Shigeomi Watanabe 1470 Shiraoka, Shiraoka-cho, Minami-Saitama-gun, Saitama 1470 Nissan Kagaku Industry Co., Ltd., Biological Science Research Institute (72) Inventor Kimihiro Ishikawa 1470 Shiraoka, Shiraoka-cho, Minamisaitama-gun, Saitama Nissan Chemical Industry Co., Ltd. Biological Science Research Institute

Claims (2)

[Claims] 1. Formula (1):[In the formula, R¹Is a hydrogen atom, which may be replaced by a
C_1-6Alkyl group (a is a halogen atom, C_1-6Arcoki
Shi group, C_2-6Alkoxycarbonyl group, C_2-6Alkyl
Carbonyloxy group, C_2-6Alkylcarbonylamino
Groups, same or different C_1-61 depending on the alkyl group
Ishi 2-disubstituted amino group, C_2-6Alkyl carbonyl
Group selected from the group consisting of cyano group and nitro group
Represents a substituent. ), C optionally substituted by a_3-8Shi
Chloroalkyl group, C optionally substituted by a_2-7A
Lucenyl group, C optionally substituted by a_2-7Archi
Nyl group, C optionally substituted by a_1-6Alkyls
Rufonyl group, C optionally substituted by di (a_1-6A
Alkyl) aminocarbonyl group, substituted by di (a
May be C_1-6Alkyl) aminosulfonyl group, by b
A phenyl group (b is C_1-6Alkyl
Base, C_1-6Halogenoalkyl group, C_2-6An alkenyl group,
C_2-6Halogenoalkenyl group, C_2-6Alkynyl group,
Phenyl group, halogen atom, C_1-6Alkoxy group, C_1-6
Halogenoalkoxy group, C_2-6Alkenyloxy group, C
_2-6Alkynyloxy group, phenoxy group, C_1-6Archi
Ruthio group, C_1-6Halogenoalkylthio group, C_1-6Al
Killsulfonyl group, C_1-6Halogenoalkylsulfonyl
Base, C_2-8Alkoxyalkyl group, C_2-6Alkoxyca
Rubonyl group, C_2-6Alkylcarbonyloxy group, C
_2-6Alkylcarbonylamino group, same or different
C_1-6Amino substituted by 1 to 2 with an alkyl group
Base, C_2-6Alkylcarbonyl group, benzoyl group, shear
The substituents selected from one or more groups selected from
You ), An aromatic heterocyclic group optionally substituted by b
(Aromatic heterocyclic groups are thienyl, furyl, pyrazolyl
Group, imidazolyl group, 1,2,4-triazolyl group, thia
Azolyl group, isothiazolyl group, 1,3,4-thiadia
Zolyl group, oxazolyl group, isoxazolyl group, 1,
3,4-oxadiazolyl group, pyridyl group, pyrimidyl
Group, pyridazyl group, pyrazyl group, S-triazyl group or
Represents a 1,2,4-triazyl group. ) Or b
An aralkyl group in which an phenyl group may be substituted (aralkyl
The group is C substituted by a phenyl group_1-6Alkyl group
Represent ), R²And R³Are each independently a hydrogen atom, a
C which may be substituted_{1- 6}Alkyl group, substituted by a
May be C_2-7Alkenyl group, substituted by a
Good C_2-7Alkynyl group, optionally substituted by a
I C_1-6Alkylthio group, optionally substituted by a
C_1-6An alkylsulfinyl group, substituted by a
Good C_1-6Alkylsulfonyl group, which may be substituted
Aminocarbonyl group (substituent is C_1-6Alkoxy group, C
_2-6Alkoxycarbonyl group, C _2-6Alkyl Carboni
Luoxy group, C_2-6Alkylcarbonylamino group, same
Or different C_1-61 to 2 depending on the alkyl group
A substituted amino group, C_2-6Alkylcarbonyl group and
C, which may be substituted by a)
_1-6Alkylaminocarbonyl group, substituted by di (a
May be done C_1-6Alkyl) aminocarbonyl group, a
C which may be replaced by_1-6Alkylaminosulfo
Nyl group, C optionally substituted by di (a_1-6Archi
A) aminosulfonyl group, halogen atom, a
C that may be exchanged_1-6Alkoxy group, substituted by a
May be C_2-6An alkoxycarbonyl group, by a
C which may be substituted_2-6An alkylcarbonyloxy group,
C optionally substituted by a _2-6Alkyl carbonyl
Amino group, same or different C_1-6By an alkyl group
1 to 2 substituted amino group, substituted by a
May be C_2-6Alkylcarbonyl group, -CR^Five= NO
-R⁶Group (R^FiveAnd R⁶Are each independently C_{1- 6}Al
Kill group or C_1-6Represents an alkoxy group. ), Benzo
Group, cyano group, hydroxyl group, mercapto group,
Toro group, a phenyl group optionally substituted by b, to b
A phenoxy group which may be substituted by
Optionally aromatic heterocyclic group (aromatic heterocyclic group is thienyl
Group, furyl group, pyrazolyl group, imidazolyl group, 1,
2,4-triazolyl group, thiazolyl group, isothiazolyl
Group, 1,3,4-thiadiazolyl group, oxazolyl
Group, isoxazolyl group, 1,3,4-oxadiazoli
Group, pyridyl group, pyrimidyl group, pyridazyl group, pyra
Zyl group, S-triazyl group or 1,2,4-triazyl
Represents a group. ) Or b even if the phenyl group is substituted
Good aralkyl groups (aralkyl groups are
The substituted C_1-6Represents an alkyl group. ), R^FourIs C optionally substituted by a_1-6An alkyl group,
C optionally substituted by a_2-7Alkenyl group, on a
Thus may be replaced by C_2-7Alkynyl group, depending on b
An aryl group which may be substituted by (an aryl group is phenyl
Represents a group or a naphthyl group. ), Even if replaced by b
Good aromatic heterocyclic group (the aromatic heterocyclic group is a thienyl group,
Ryl group, pyrazolyl group, imidazolyl group, 1,2,4-
Triazolyl group, thiazolyl group, isothiazolyl group,
1,3,4-thiadiazolyl group, oxazolyl group, iso
Oxazolyl group, oxadiazolyl group, pyridyl group, pi
Rimidyl group, pyridazyl group, pyrazyl group, S-triazi
Group or 1,2,4-triazyl group. ) Or b
Therefore, an aralkyl group (aralkyl group) which may be substituted on the phenyl group
Ralalkyl group is C substituted by phenyl group_1-6Al
Represents a kill group. ), X is S (O)_n, OS (O)_nOr NR⁷S (O)
_n(N represents an integer of 0 to 2 and R⁷Is a hydrogen atom, C
_1-6Alkyl group, C_2-7Alkenyl group, C_2-7Alkini
Lu group, C_1-6Alkylsulfonyl group, C_1-6Alkyla
Minocarbonyl group, C optionally substituted by di (a
_1-6An alkyl) aminocarbonyl group, substituted by a
May be C_1-6Alkylaminosulfonyl group, di (a
C which may be replaced by_1-6Alkyl) aminosul
Honyl group, C_2-6Alkoxycarbonyl group, C_2-6Al
A phenyl group is replaced by a carbonyl group or b
Aralkyl groups which may be
Replaced by C_1-6Represents an alkyl group. )]
A pyrazole derivative or a salt thereof. . 2. The pyrazole derivative according to claim 1 or 2
A herbicide containing the above as an active ingredient.