JPH11130607A - Granular wettable dust for agriculture - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an agricultural preparation having excellent disintegration and dispersion in water. SOLUTION: This granular wettable dust comprises (A) a compound of formula I [Q is a (substituted) heterocyclic ring group or a (substituted) hydrocarbon group, W is O or S; R<1> and R<2> are each an alkyl group, an alkoxy group or a halogen atom, Z is CH or N] or its salt, (B) a polycarboxylic acid surfactant or a formaldehyde condensate with an aromatic sulfonic acid derivative or its salt and (C) a ligninsulfonate salt.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a water dispersible agricultural granule having good disintegration in water and high dispersion stability.

[0002]

2. Description of the Related Art Water dispersible granules are granules that are completely and easily dispersed in water, and are easier to handle, easier to measure, prevent dust, and easier to apply than conventional wettable powders. It is an excellent pesticide formulation in terms of. However, if the preparation is granulated as it is using the conventional wettable powder formulation, there are various problems that it does not easily disintegrate in water and a stable dispersion cannot be obtained. JP-A-1-38091 describes a sulfonylurea compound having excellent selective herbicidal activity. Japanese Patent Publication No. 6-99245 discloses a pesticide active ingredient,
And a copolymer of acrylic acid and itaconic acid having a molecular weight of 5,000 to 20,000, a copolymer of methacrylic acid and itaconic acid, a copolymer of maleic acid and styrene, a copolymer of maleic acid and diisobutylene, and alkalis thereof. A particulate hydratable pesticide composition containing one or more polycarboxylic acid surfactants selected from salts with metals, ammonia or amines is described. Also, JP-A-6-12
No. 8102 describes a particulate wettable powder containing an agricultural chemical active ingredient, a surfactant and diatomaceous earth.

[0003]

The sulfonylurea compounds are not easily disintegrated in water with conventional water dispersible granules.
It has the disadvantage that a stable dispersion cannot be obtained. Therefore, in order to more efficiently exhibit the excellent herbicidal ability of the sulfonylurea compound, development of a water dispersible granule having good disintegration in water and dispersibility in water has been desired.

[0004]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, the formula [I]

Embedded image [In the formula, Q represents an optionally substituted heterocyclic group or an optionally substituted hydrocarbon group, W represents an oxygen atom or a sulfur atom, and R ¹ and R ² represent an alkyl group, an alkoxy group or a halogen, respectively. An atom, Z represents CH or N. By adding a polycarboxylic acid surfactant or a formalin condensate of an aromatic sulfonic acid derivative or a salt thereof, and a lignin sulfonate to a wettable powder containing a sulfonylurea compound or a salt thereof represented by Unexpectedly, it succeeded in imparting good disintegration and dispersibility in water. The present inventors have further studied based on this finding, and as a result, have completed the present invention.

That is, the present invention relates to [1] Formula [I]

Embedded image [In the formula, Q represents an optionally substituted heterocyclic group or an optionally substituted hydrocarbon group, W represents an oxygen atom or a sulfur atom, and R ¹ and R ² represent an alkyl group, an alkoxy group or a halogen, respectively. An atom, Z represents CH or N. (Hereinafter sometimes simply referred to as compound (I)) or a salt thereof, (2) a formalin condensate of a polycarboxylic acid surfactant or an aromatic sulfonic acid derivative or a salt thereof, and (3) A water dispersible granule containing a lignin sulfonate, [2] the compound represented by the formula [I] is N- (2-chloroimidazo [1,2-
a] Pyridin-3-ylsulfonyl) -N '-(4,6
-Dimethoxy-2-pyrimidinyl) urea; [3] the compound represented by the formula [I], wherein the compound represented by the formula [I] is N- (2-ethylsulfonylimidazo [1,
2-a] pyridin-3-ylsulfonyl) -N ′-(4,
6-dimethoxy-2-pyrimidinyl) urea; the water dispersible granule according to the above-mentioned [1]; 70 to 95% by weight of the water dispersible granule according to the above [1], [5] the compound represented by the formula [I] or a salt thereof, and other agrochemical active ingredients.
[4] above, wherein the water dispersible granule according to [4] above, [6] a polycarboxylic acid surfactant or a formalin condensate of an aromatic sulfonic acid derivative or a salt thereof is contained in an amount of 1 to 15% by weight. The water dispersible granule according to the above [7], which contains 1 to 15% by weight of ligninsulfonate, and the water wettable granule according to the above [4], wherein the average particle diameter is 0.1 to 5 mm. 1] The water dispersible granule according to the above item,

[9] (1) a compound represented by the formula [I] or a salt thereof, (2) a formalin condensate of a polycarboxylic acid surfactant or an aromatic sulfonic acid derivative or a salt thereof, and (2) a lignin sulfonic acid salt Is mixed and granulated.
The method for producing a water-dispersible granule according to the above-mentioned [1], wherein the method for producing a water-dispersible granule according to the above-mentioned [1], which is sprayed on a paddy field, a field, an orchard, a turf or a non-agricultural land, And [1
1) The use according to the above item [10], wherein the water dispersible granule according to the above item [1] is diluted 100 to 20,000 times with water before spraying.

In the above formula [I], Q represents an optionally substituted heterocyclic group or an optionally substituted hydrocarbon group. As the optionally substituted heterocyclic group,
For example, a 3- to 8-membered heterocyclic group containing 1 to 4 heteroatoms such as a nitrogen atom (which may be oxidized), an oxygen atom, a sulfur atom (which may be mono- or dioxidized) (preferably 5 to 6-membered heterocyclic group) or 3 to 3 containing 1 to 4 heteroatoms such as a nitrogen atom (which may be oxidized), an oxygen atom, and a sulfur atom (which may be mono- or dioxide-oxidized). An 8-membered heterocyclic group (preferably a 5- to 6-membered heterocyclic group) and a benzene ring or a nitrogen atom (which may be oxidized), an oxygen atom, a sulfur atom (which may be mono- or dioxidized), etc. A group formed by condensing a 3- to 8-membered heterocyclic group containing 1 to 4 heteroatoms (preferably a 5- to 6-membered heterocyclic group), preferably a 5- to 6-membered heterocyclic group and a nitrogen atom (oxide May be used) Oxygen atom, a sulfur atom (mono- or dioxides of are also may optionally) 1 hetero atom such as to four which may contain 5-6 membered ring include groups formed by condensation.

Specifically, aziridinyl (eg, 1- or 2-aziridinyl), aziridinyl (eg, 1- or 2
-Azilinyl), azetyl (eg, 2-, 3- or 4-
Azetyl), azetidinyl (eg, 1-, 2- or 3-
Azetidinyl), perhydroazepinyl (eg, 1-, 2
-, 3- or 4-perhydroazepinyl), perhydroazosinyl (eg, 1-, 2-, 3-, 4- or 5-
Perhydroazosinyl), pyrrolyl (eg, 1-, 2- or 3-pyrrolyl), pyrazolyl (eg, 1-, 3-, 4)
-Or 5-pyrazolyl), imidazolyl (eg, 1-,
2-, 4- or 5-imidazolyl), triazolyl (eg, 1,2,3-triazole-1-, 4- or-
5-yl, 1,2,4-triazol-1-, 3-, 4
-Or 5-yl), tetrazolyl (eg, tetrazol-1-, 2- or 5-yl), furyl (eg, 2- or 3-furyl), thienyl (eg, 2- or 3-thienyl), sulfur atom Is oxidized (eg, 2- or 3-thienyl-1,1-dioxide), oxazolyl (eg, 2-, 4- or 5-oxazolyl), isoxazolyl (eg, 3-, 4- or 5-isoxazolyl) ),
Oxdiazolyl (eg, 1,2,3-oxadiazol-4- or 5-yl, 1,2,4-oxadiazol-3- or 5-yl, 1,2,5-oxadiazole-3- Yl, 1,3,4-oxadiazol-2-yl), thiazolyl (eg, 2-, 4- or 5-thiazolyl), isothiazolyl (eg, 3-, 4- or 5-isothiazolyl), thiadiazolyl (example) 1,2,3-thiadiazol-4- or 5-yl, 1,2,4-thiadiazol-3- or 5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-thiadiazole -2-
Yl), pyrrolidinyl (eg, 1-, 2- or 3-pyrrolidinyl), pyridyl (eg, 2-, 3- or 4-pyridyl), pyridyl having a nitrogen atom oxidized (eg, 2-, 3)
-Or 4-pyridyl-N-oxide), pyridazinyl (eg, 3- or 4-pyridazinyl), pyridazinyl in which one or both of the nitrogen atoms are oxidized (eg, 3-, 4
-, 5- or 6-pyridazinyl-N-oxide), pyrimidinyl (eg, 2-, 4- or 5-pyrimidinyl), pyrimidinyl in which one or both of the nitrogen atoms are oxidized (eg, 2-, 4-, 5) -Or 6-pyrimidinyl-
N-oxide), pyrazinyl, piperidinyl (eg, 1
-, 2-, 3- or 4-piperidinyl), piperazinyl (eg, 1- or 2-piperazinyl), indolyl (eg, 3H-indole-2-, 3-, 4-, 5-, 6)
-Or 7-yl), pyranyl (eg, 2-, 3- or 4-pyranyl), thiopyranyl (eg, 2-, 3- or 4-thiopyranyl), thiopyranyl having a sulfur atom oxidized (eg, 2-, 3- or 4-thiopyranyl) 3- or 4-thiopyranyl-1,1-
Dioxide), morpholinyl (eg, 2-, 3- or 4
-Morpholinyl), thiomorpholinyl, quinolyl (eg,
2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl), isoquinolyl, pyrido [2,3-d] pyrimidinyl (eg, pyrido [2,3-d] pyrimidin-2-yl ), 1,5-, 1,6-, 1,7-, 1,8-, 2
Naphthyridinyl such as 6- or 2,7-naphthyridinyl (eg, 1,5-naphthyridin-2- or 3-yl), thieno [2,3-d] pyridyl (eg, thieno [2,3-d] pyridine- 3-yl), pyrazinoquinolyl (eg, pyrazino [2,3-d] quinolin-2-yl), chromenyl (eg, 2H-chromen-2- or 3)
-Yl), imidazo [1,2-a] pyridyl, imidazo [2,1-b] thiazolyl, imidazo [1,2-a] pyrimidinyl, imidazo [1,2-b] pyridazinyl, imidazo [1,2- c] pyrimidinyl, imidazo [1, 2
-A] imidazolyl, imidazo [2,1-b] (1,
3,4) thiadiazolyl, 2,3-dihydroimidazo [2,1-b] thiazolyl (or its monooxide or dioxide), pyrazolo [1,5-a] pyrimidinyl,
Pyrazolo [5,1-b] thiazolyl, pyrazolo [1,5
-A] pyridyl, pyrrolo [1,2-a] pyridyl, imidazo [1,5-a] pyridyl, imidazo [1,2-b]
(1,2,4) triazolyl, (1,2,4) triazolo [3,4-b] thiazolyl and the like are used. In addition,
The above imidazo [1,2-a] pyridyl, imidazo [2,
1-b] thiazolyl, imidazo [1,2-a] pyrimidinyl, imidazo [1,2-b] pyridazinyl, imidazo [1,2-c] pyrimidinyl, imidazo [1,2-a]
Imidazolyl, imidazo [2,1-b] (1,3,4)
Thiadiazolyl, 2,3-dihydroimidazo [2,1-
b] thiazolyl (or its monooxide or dioxide), pyrazolo [1,5-a] pyrimidinyl, pyrazolo [5,1-b] thiazolyl, pyrazolo [1,5-a] pyridyl, pyrrolo [1,2-a] Pyridyl, imidazo [1,5-a] pyridyl, imidazo [1,2-b]
(1,2,4) triazolyl and (1,2,4) triazolo [3,4-b] thiazolyl are

Embedded image 1 hydrogen atom bonded to a constituent carbon atom other than the bridgehead atom
It is a group formed by removing individual pieces. In particular, pyrazolyl,
Imidazo [1,2-a] pyridyl, imidazo [2,1-
b] Thiazolyl and imidazo [1,2-b] pyridazinyl are preferred.

The heterocyclic group is selected from the group consisting of, for example, a hydroxy group, an amino group, a cyano group, a sulfamoyl group, a sulfamoyloxy group, a mercapto group, a nitro group, a halogen atom, an organic residue and a sulfo group. It may be substituted with the same or different 1 to 3 substituents. Of the above substituents, preferred are a cyano group, a nitro group, a halogen atom or an organic residue. Particularly preferred are a halogen atom and an organic residue. Here, examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like. Examples of the organic residue include a hydrocarbon group, a heterocyclic group, an acyl group, a formula -TR ³ [wherein R ³ is a hydrocarbon group, a heterocyclic group or an acyl group, and T is O,

Embedded image Or SS, and k represents 0, 1 or 2], a group represented by the formula:

Embedded image Wherein R ⁴ represents a hydrogen atom, a hydrocarbon group or an acyl group, R ⁵ represents a hydrocarbon group or an acyl group, or R ⁴ and R ⁵ may form a ring together with an adjacent nitrogen atom . Group and formula

Embedded image Wherein the symbols in the formula are as defined above, a carbamoyl group which may be substituted, a carbamoyloxy group which may be substituted, a ureido group which may be substituted, which may be thiocarbamoyl group, wherein, R ⁵ is as defined above] carboxyl group, or a group of the formula -O-SO ₂ -R ⁵ such as a group represented by the like.

The hydrocarbon group, heterocyclic group, acyl group, hydrocarbon group represented by R ³ , heterocyclic group, acyl group, and hydrocarbon group represented by R ⁴ or R ⁵ , acyl group The groups are described in detail below. The above-mentioned carbamoyl group, carbamoyloxy group, or thiocarbamoyl group may be substituted with one or two identical or different hydrocarbon groups, heterocyclic groups or acyl groups described in detail below. The above ureido group may be substituted with 1 to 3 identical or different hydrocarbon groups, heterocyclic groups or acyl groups which will be described in detail below. The heterocyclic group as the organic residue and the heterocyclic group for R ³ may be substituted with 1 to 3 hydrocarbon groups, acyl groups, and halogen atoms described in detail below.

Examples of the hydrocarbon group include an aliphatic hydrocarbon group which can have a linear, branched or cyclic double bond or triple bond, an aryl group or an aralkyl group. Specifically, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group and the like are used, and among them, a C _1-19 hydrocarbon group and the like are preferable. The alkyl group preferably includes a linear or branched alkyl group having 1 to 6 carbon atoms or a cyclic alkyl group having 3 to 14 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n -Butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, isohexyl, cyclohexyl and other C _1-6 alkyl groups and C _3-14 cycloalkyl groups Are used. The alkenyl group preferably includes a linear or branched alkenyl group having 2 to 6 carbon atoms or a cyclic alkenyl group having 3 to 14 carbon atoms, such as allyl, isopropenyl, isobutenyl, 2-pentenyl, C _2-6 alkenyl groups such as 2-hexenyl and 2-cyclohexenyl, and C _3-14 alkenyl groups are used. The alkynyl group is preferably an alkynyl group having 2 to 6 carbon atoms, for example, a C _2-6 alkynyl group such as propargyl, 2-butynyl, 3-butynyl, 3-pentynyl, 3-hexynyl and the like are used. . The aryl group is preferably an aryl group having 6 to 14 carbon atoms, such as phenyl, naphthyl, and anthryl.
The aralkyl group preferably has 7 to 19 carbon atoms.
And phenyl-C _1-4 alkyl such as benzyl, phenethyl and phenylpropyl, benzhydryl, trityl and the like.

When the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, 1 to 3 alkylthio groups (eg, C _1-4 alkylthio such as methylthio, ethylthio, n-propylthio, isopropylthio, etc.);
Halogen (eg, fluorine, chlorine, bromine, iodine), alkoxy group (eg, methoxy, ethoxy, n-propoxy, ter)
C _1-6 alkoxy such as t-butoxy and n-hexyloxy, etc., nitro group, alkoxy-carbonyl group (eg, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxy) Carbonyl, sec-butoxycarbonyl, C _1-6 alkoxy-carbonyl such as tert-butoxycarbonyl, etc.), alkylamino group (eg,
Methylamino, ethylamino, n-propylamino, n-
Mono- or di- such as butylamino, tert-butylamino, n-pentylamino, n-hexylamino, dimethylamino, diethylamino, methylethylamino, di- (n-propyl) amino, di- (n-butyl) amino −
C _1-6, etc. alkylamino), alkoxyimino groups (e.g., methoxyimino, ethoxyimino, n- propoxyimino, tert- Butokishiimino, n- hexyloxy - a C _1-6 alkoxyimino imino) or hydroxyimino May be substituted. When the hydrocarbon group is an aryl group or an aralkyl group, 1 to 5
(Preferably 1 to 3) alkyl groups (eg, methyl,
Ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, se
C _1-6 alkyl such as c-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, C _3-6 cycloalkyl such as cyclohexyl, etc., alkenyl group (eg, allyl, isopropenyl, isobutenyl, 1-methylallyl, 2 -C such as pentenyl, 2-hexenyl
_2-6 such alkenyl), alkynyl group (e.g., propargyl, 2-butynyl, 3-butynyl, 3-pentynyl, 3
-Hexynyl and other C _2-6 alkynyl, etc.), alkoxy groups (eg, methoxy, ethoxy, n-propoxy, tert.
-Butoxy, C _1-6 alkoxy such as n-hexyloxy, etc.), acyl group [eg, C _1-7 alkanoyl such as formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl, heptanoyl, etc .; benzoyl, naphthalenecarbonyl, etc. C _6-14 aryl-
Carbonyl; methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, se
C _1-6 alkoxy-carbonyl such as c-butoxycarbonyl, tert-butoxycarbonyl; C _6-14 aryloxy-carbonyl such as phenoxycarbonyl; phenyl-C _1-4 alkylcarbonyl (eg, benzylcarbonyl, phenethylcarbonyl, phenylpropyl C _7-19 aralkyl such as ylcarbonyl etc.) - carbonyl; phenyl -C _1-4 alkyloxycarbonyl (e.g., benzyloxycarbonyl), such as C _7-19 aralkyloxycarbonyl such as, nitro, amino, hydroxy, cyano , Sulfamoyl, mercapto, halogen (eg, fluorine, chlorine, bromine, iodine), or an alkylthio group (C _1-4 alkylthio such as methylthio, ethylthio, n-propylthio, isobutylthio, etc.).

Examples of the heterocyclic group include a heterocyclic group containing 1 to 4 heteroatoms such as a nitrogen atom (which may be oxidized), an oxygen atom, and a sulfur atom (which may be mono- or dioxidized). Or a heterocyclic group such as a nitrogen atom (which may be oxidized), an oxygen atom, or a sulfur atom (which may be mono- or dioxidized). A 3- to 8-membered heterocyclic group containing 1 to 4 atoms (preferably a 5- to 6-membered heterocyclic group) and a benzene ring or a nitrogen atom (which may be oxidized), an oxygen atom, a sulfur atom (mono or dioxide) And a 3- to 8-membered heterocyclic group containing 1 to 4 heteroatoms (preferably a 5- to 6-membered heterocyclic group). Membered heterocyclic group and nitrogen atom Formed by condensing with a 5- to 6-membered ring which may contain 1 to 4 heteroatoms such as an oxidized group, an oxygen atom and a sulfur atom (which may be mono- or di-oxidized). Group.
Specifically, aziridinyl (eg, 1- or 2-aziridinyl), azilinyl (eg, 1- or 2-azilinyl), azetyl (eg, 2-, 3- or 4-azetyl), azetidinyl (eg, 1- , 2- or 3-azetidinyl), perhydroazepinyl (eg, 1-, 2-, 3
-Or 4-perhydroazepinyl), perhydroazosinyl (eg, 1-, 2-, 3-, 4- or 5-perhydroazosinyl), pyrrolyl (eg, 1-, 2- or 3
-Pyrrolyl), pyrazolyl (eg, 1-, 3-, 4- or 5-pyrazolyl), imidazolyl (eg, 1-, 2-,
4- or 5-imidazolyl), triazolyl (eg,
1,2,3-triazol-1-, 4- or -5-yl, 1,2,4-triazol-1-, 3-, 4- or 5-yl), tetrazolyl (eg, tetrazol-1)
-, 2- or 5-yl), frills (eg, 2- or 3
-Furyl), thienyl (eg, 2- or 3-thienyl), thienyl having a sulfur atom oxidized (eg, 2- or 3-thienyl-1,1-dioxide), oxazolyl (eg, 2-, 4- or 5-oxazolyl), isoxazolyl (eg, 3-, 4- or 5-isoxazolyl),
Oxdiazolyl (eg, 1,2,3-oxadiazol-4- or 5-yl, 1,2,4-oxadiazol-3- or 5-yl, 1,2,5-oxadiazole-3- Yl, 1,3,4-oxadiazol-2-yl), thiazolyl (eg, 2-, 4- or 5-thiazolyl), isothiazolyl (eg, 3-, 4- or 5-isothiazolyl), thiadiazolyl (example) 1,2,3-thiadiazol-4- or 5-yl, 1,2,4-thiadiazol-3- or 5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-thiadiazole -2-
Yl), pyrrolidinyl (eg, 1-, 2- or 3-pyrrolidinyl), pyridyl (eg, 2-, 3- or 4-pyridyl), pyridyl having a nitrogen atom oxidized (eg, 2-, 3)
-Or 4-pyridyl-N-oxide), pyridazinyl (eg, 3- or 4-pyridazinyl), pyridazinyl in which one or both of the nitrogen atoms are oxidized (eg, 3-, 4
-, 5- or 6-pyridazinyl-N-oxide), pyrimidinyl (eg, 2-, 4- or 5-pyrimidinyl), pyrimidinyl in which one or both of the nitrogen atoms are oxidized (eg, 2-, 4-, 5) -Or 6-pyrimidinyl-
N-oxide), pyrazinyl, piperidinyl (eg, 1
-, 2-, 3- or 4-piperidinyl), piperazinyl (eg, 1- or 2-piperazinyl), indolyl (eg, 3H-indole-2-, 3-, 4-, 5-, 6)
-Or 7-yl), pyranyl (eg, 2-, 3- or 4-pyranyl), thiopyranyl (eg, 2-, 3- or 4-thiopyranyl), thiopyranyl having a sulfur atom oxidized (eg, 2-, 3- or 4-thiopyranyl) 3- or 4-thiopyranyl-1,1-
Dioxide), morpholinyl (eg, 2-, 3- or 4
-Morpholinyl), thiomorpholinyl, quinolyl (eg,
2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl), isoquinolyl, pyrido [2,3-d] pyrimidinyl (eg, pyrido [2,3-d] pyrimidin-2-yl ), 1,5-, 1,6-, 1,7-, 1,8-, 2
Naphthyridinyl such as 6- or 2,7-naphthyridinyl (eg, 1,5-naphthyridin-2- or 3-yl), thieno [2,3-d] pyridyl (eg, thieno [2,3-d] pyridine- 3-yl), pyrazinoquinolyl (eg, pyrazino [2,3-d] quinolin-2-yl), chromenyl (eg, 2H-chromen-2- or 3)
-Yl) is used.

Examples of the acyl group include an acyl group having 1 to 20 carbon atoms derived from an organic carboxylic acid.
For example, an alkanoyl group, preferably an alkanoyl group having 1 to 7 carbon atoms (eg, formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl, heptanoyl, etc.), an arylcarbonyl group, preferably an aryl- group having 6 to 14 carbon atoms Carbonyl group,
(Eg, benzoyl, naphthalenecarbonyl, etc.), an alkoxycarbonyl group, preferably an alkoxycarbonyl group having 1 to 6 carbon atoms (eg, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec- Butoxycarbonyl, tert-butoxycarbonyl, etc.), an aryloxycarbonyl group, preferably an aryloxy-carbonyl group having 6 to 14 carbon atoms (eg,
Phenoxycarbonyl group), aralkylcarbonyl group,
Preferably an aralkyl-carbonyl group having 7 to 19 carbon atoms (eg, benzylcarbonyl, phenethylcarbonyl,
Phenyl-C _1-4 alkylcarbonyl such as phenylpropylcarbonyl, naphthyl-C _1-4 alkylcarbonyl such as benzhydrylcarbonyl and naphthylethylcarbonyl), an aralkyloxycarbonyl group, preferably an aralkyloxy group having 7 to 19 carbon atoms. -Carbonyl group (eg, phenyl-C such as benzyloxycarbonyl)
_1-4 -alkyloxycarbonyl, etc.) 5- or 6-membered heterocyclic carbonyl group or a condensed heterocyclic carbonyl group (eg, pyrrolylcarbonyl such as 2- or 3-pyrrolylcarbonyl; 3-, 4- or 5- Pyrazolylcarbonyl such as pyrazolylcarbonyl; imidazolylcarbonyl such as 2-, 4- or 5-imidazolylcarbonyl; tria such as 1,2,3-triazol-4-ylcarbonyl, 1,2,4-triazol-3-ylcarbonyl Zolylcarbonyl; tetrazolylcarbonyl such as 1H- or 2H-tetrazol-5-ylcarbonyl; furylcarbonyl such as 2- or 3-furylcarbonyl; thienylcarbonyl such as 2- or 3-thienylcarbonyl; -Or 5-oxazolylcarbonyl No doubt Lil carbonyl; 3-, 4
-Or isoxazolylcarbonyl such as 5-isoxazolylcarbonyl; 1,2,3-oxadiazole-4
-Or 5-ylcarbonyl, 1,2,4-oxadiazol-3- or 5-ylcarbonyl, 1,2,5-
Oxadiazol-3- or 4-ylcarbonyl,
Oxadiazolylcarbonyl such as 1,3,4-oxadiazol-2-ylcarbonyl; 2-, 4- or 5
Thiazolylcarbonyl, such as thiazolylcarbonyl;
Isothiazolylcarbonyl such as 3-, 4- or 5-isothiazolylcarbonyl; 1,2,3-thiadiazole-4- or 5-ylcarbonyl, 1,2,4-thiadiazole-3- or 5-ylcarbonyl , 1,2,
5-thiadiazole-3- or 4-ylcarbonyl,
Thiadiazolylcarbonyl such as 1,3,4-thiadiazol-2-ylcarbonyl; pyrrolidinylcarbonyl such as 2- or 3-pyrrolidinylcarbonyl;
Pyridylcarbonyl such as 3- or 4-pyridylcarbonyl; pyridylcarbonyl in which a nitrogen atom is oxidized such as 2-, 3- or 4-pyridyl-N-oxidecarbonyl; pyridylcarbonyl such as 3- or 4-pyridazinylcarbonyl Pyridazinyl in which one or both nitrogen atoms have been oxidized, such as dazinylcarbonyl; 3-, 4-, 5- or 6-pyridazinyl-N-oxidecarbonyl; 2-, 4-
Or a pyrimidinylcarbonyl such as 5-pyrimidinylcarbonyl; pyrimidinylcarbonyl having one or both nitrogen atoms oxidized, such as 2-, 4-, 5- or 6-pyrimidinyl-N-oxidecarbonyl; pyrazinylcarbonyl; Piperidinylcarbonyl, such as, 3- or 4-piperidinylcarbonyl; piperazinylcarbonyl; indolylcarbonyl, such as 3H-indole-2- or 3-ylcarbonyl; 2-, 3- or 4
Pyranylcarbonyl, such as -pyranylcarbonyl; 2
Thiopyranylcarbonyl such as-, 3- or 4-thiopyranylcarbonyl; quinolylcarbonyl such as 3-, 4-, 5-, 6-, 7- or 8-quinolylcarbonyl; isoquinolylcarbonyl; pyrido [2,3-d] pyrimidinylcarbonyl (eg, pyrido [2,3-d] pyrimidin-2-ylcarbonyl); 1,5-, 1,6-,
Naphthyridinylcarbonyl such as 1,7-, 1,8-, 2,6- or 2,7-naphthyridinylcarbonyl (eg, 1,5-naphthyridin-2- or 3-ylcarbonyl); thieno [2 , 3-d] pyridylcarbonyl (eg, thieno [2,3-d] pyridin-3-ylcarbonyl); pyrazinoquinolylcarbonyl (eg, pyrazino [2,3-b] quinolin-2-ylcarbonyl); Chromenylcarbonyl (eg, 2H-chromen-2- or 3
A 5- or 6-membered complex containing 1 to 4 heteroatoms such as a nitrogen atom (which may be oxidized), such as -ylcarbonyl, etc., an oxygen atom, and a sulfur atom (which may be mono- or dioxide-oxidized). Ring-carbonyl group), 5- or 6-membered heterocyclic-acetyl group (eg, nitrogen atom (optionally oxidized) such as 2-pyrrolylacetyl, 3-imidazolylacetyl, 5-isoxazolylacetyl); A 5- or 6-membered heterocyclic-acetyl group containing 1 to 4 heteroatoms such as an oxygen atom and a sulfur atom (which may be mono- or dioxidized) is used.

When the acyl group is an alkanoyl group or an alkoxy-carbonyl group, the acyl group has 1 to 3 alkylthio groups (eg, methylthio, ethylthio, n-
C _1-4 alkylthio such as propylthio, isopropylthio, etc.), halogen (eg, fluorine, chlorine, bromine, iodine), alkoxy group (eg, methoxy, ethoxy, n-propoxy, tert-butoxy, n-hexyloxy, etc.) C
_1-6 alkoxy, etc.), nitro group, alkoxy-carbonyl group (eg, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl C _1-6 alkoxy etc. - carbonyl, etc.), alkylamino group (e.g., methylamino, ethylamino, n- propylamino, n- butylamino, tert- butylamino, n- pentylamino, n- hexylamino, dimethylamino Amino, diethylamino, methylethylamino, di-
Mono- or di-C _1-6 alkylamino such as (n-propyl) amino, di- (n-butyl) amino and the like, alkoxyimino group (eg, methoxyimino, ethoxyimino, n-propoxyimino, tert- Butoxyimino, n-
Hexyloxy - a C _1-6 alkoxyimino imino) or hydroxyimino with may be substituted.
Further, the acyl group is an aryl-carbonyl group, an aryloxy-carbonyl group, an aralkyl-carbonyl group,
In the case of an aralkyloxycarbonyl group, a 5- or 6-membered heterocyclic-carbonyl group or a 5- or 6-membered heterocyclic-acetyl group, 1 to 5 (preferably 1 to 3) alkyl groups (eg, methyl, ethyl, n -C _1-6 alkyl such as propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, and C _3- such as cyclohexyl ₆ cycloalkyl, etc.), alkenyl group (eg, allyl, isopropenyl, isobutenyl, 1-methylallyl, 2-pentenyl, 2-
C _2-6 alkenyl such as hexenyl), alkynyl group (eg, propargyl, 2-butynyl, 3-butynyl,
C _2-6 alkynyl such as 3-pentynyl and 3-hexynyl, etc.), alkoxy group (eg, methoxy, ethoxy, n
-C _1-6 alkoxy such as propoxy, tert-butoxy, n-hexyloxy, etc.), acyl group [eg, C _1-7 alkanoyl such as formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl, heptanoyl; benzoyl And C _6-14 aryl-carbonyl such as naphthalenecarbonyl; methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-
C _1-6 alkoxy-carbonyl such as butoxycarbonyl; C _6-14 aryloxy-carbonyl such as phenoxycarbonyl; C such as phenyl-C _1-4 alkylcarbonyl (eg, benzylcarbonyl, phenethylcarbonyl, phenylpropylcarbonyl, etc.) _7-19 aralkyl-carbonyl; C such as phenyl-C _1-4 alkyloxycarbonyl (eg, benzyloxycarbonyl, etc.)
_7-19 aralkyloxycarbonyl, etc.], nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, halogen (eg, fluorine, chlorine, bromine, iodine), or alkylthio group (methylthio, ethylthio, n-propylthio, isobutylthio, etc.) C _1-4 alkylthio).

The group represented by the formula -TR ³ is specifically, for example, an alkyloxy group, an alkenyloxy group, an aryloxy group, an aralkyloxy group, a heterocyclic-oxy group, an acyloxy group, an alkylthio group, Alkenylthio, arylthio, aralkylthio, heterocyclic thio, acylthio, alkyldithio, aryldithio, aralkyldithio, alkylsulfinyl, alkenylsulfinyl, arylsulfinyl, aralkylsulfinyl, heterocycle- A sulfinyl group, an alkylsulfonyl group, an alkenylsulfonyl group, an arylsulfonyl group, an aralkylsulfonyl group, and a heterocyclic-sulfonyl group. The alkyloxy group preferably includes a linear, branched or cyclic alkyloxy group having 1 to 6 carbon atoms, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec. -Butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, isopentyloxy, neopentyloxy, cyclopentyloxy, n-
A C _1-6 alkoxy group such as hexyloxy, isohexyloxy, cyclohexyloxy or a C _3-6 cycloalkyloxy group is used. The alkenyloxy group is preferably a straight-chain, branched or cyclic alkenyloxy group having 2 to 6 carbon atoms, for example, allyloxy, isopropenyloxy, 1-butenyloxy, 2
C _2-6 such as pentenyloxy, 2-hexenyloxy and the like
An alkenyloxy group or a C _3-6 cycloalkenyloxy group is used. The aryloxy group is preferably an aryloxy group having 6 to 14 carbon atoms, for example, phenoxy, naphthyloxy and the like. The aralkyloxy group is preferably an aralkyloxy group having 7 to 19 carbon atoms. For example, phenyl-C _1-4 alkyloxy such as benzyloxy, phenethyloxy and phenylpropyloxy is used.

The heterocyclic-oxy group is represented by the formula T'-
A group represented by O- (T ′ has the same meaning as the above-mentioned heterocyclic group for R ³ ), and specifically, pyrrolyloxy such as 2- or 3-pyrrolyloxy;
Or pyrazolyloxy such as 5-pyrazolyloxy;
Imidazolyloxy such as 2-, 4- or 5-imidazolyloxy; triazolyloxy such as 1,2,3-triazol-4-yloxy, 1,2,4-triazol-3-yloxy; 1H- or 2H- Tetrazolyloxy such as tetrazol-5-yloxy; furyloxy such as 2- or 3-furyloxy; thienyloxy such as 2- or 3-thienyloxy; 2- or 3-thienyloxy-1,1-dioxide and the like Thienyloxy in which the sulfur atom of is oxidized; 2-, 4- or 5-
Oxazolyloxy such as oxazolyloxy is used. The acyloxy group includes a compound of the formula T ″ —O—
(T ″ has the same meaning as the above-mentioned acyl group for R ³ ), specifically, acetoxy,
C _1-6 alkyl-carbonyloxy such as propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy; C _7-19 aralkyl of phenyl-C _1-4 alkylcarbonyloxy (eg, benzylcarbonyloxy, phenethylcarbonyloxy, etc.) Carbonyloxy; C _6-14 such as benzoyloxy and naphthoyloxy
Arylcarbonyloxy; heterocyclic carbonyloxy such as thienylcarbonyloxy, benzothienylcarbonyloxy and the like are used. The alkylthio group is preferably a straight-chain, branched or cyclic alkylthio group having 1 to 6 carbon atoms, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio. Butylthio, tert-butylthio, n-pentylthio, sec-pentylthio, isopentylthio, neopentylthio, cyclopentylthio, n-hexylthio, isohexylthio,
A C _1-6 alkylthio group such as cyclohexylthio or a C _3-6 cycloalkylthio group is used. The alkenylthio group is preferably a straight-chain, branched or cyclic alkenylthio group having 2 to 6 carbon atoms, for example, allylthio, isopropenylthio, 1-butenylthio, 2-pentenylthio, 2-hexenyl Thio,
A C _2-6 alkenylthio group such as cyclohexenylthio or a C _3-6 cycloalkenylthio group is used.

The arylthio group is preferably an arylthio group having 6 to 14 carbon atoms, such as phenylthio and naphthylthio. The aralkylthio group is preferably an aralkylthio group having 7 to 19 carbon atoms, for example, phenyl-C such as benzylthio, phenethylthio and phenylpropylthio.
_1-4 alkylthio and the like are used. The heterocyclic thio groups include a group represented by the formula T'-S- (T 'is as defined heterocyclic group in R ³ mentioned above), specifically, 2- or 3 Pyrrolylthio such as -pyrrolylthio; pyrazolylthio such as 3-, 4- or 5-pyrazolylthio; imidazolylthio such as 2-, 4- or 5-imidazolylthio; 1,2,3-triazole-4-
Triazolylthio such as ylthio, 1,2,4-triazol-5-ylthio; tetrazolylthio such as 1H- or 2H-tetrazol-5-ylthio; furylthio such as 2- or 3-furylthio; thienylthio such as 2- or 3-thienylthio. Thienylthio in which the sulfur atom of a thienyl group such as 2- or 3-thienylthio-1,1-dioxide is oxidized; oxazolylthio such as 2-, 4- or 5-oxazolylthio;
Examples of the acylthio group include groups represented by the formula T ″ —S— (T ″ represents the acyl group described above), and specifically, acetylthio, propionylthio, butyrylthio,
C _1-6 alkylcarbonylthio such as pentanoylthio and hexanoylthio; phenyl-C _1-4 alkylthio such as benzylcarbonylthio and phenethylcarbonylthio; C _6-14 arylcarbonylthio such as benzoylthio and naphthoylthio; thienylcarbonyl Heterocyclic carbonylthio such as thio, benzothienylcarbonylthio and the like are used. The alkyldithio group is preferably a straight-chain, branched or cyclic alkyldithio group having 1 to 6 carbon atoms, for example, C _1-6 alkyldithio such as methyldithio, ethyldithio, n-propyldithio and cyclopentyldithio. Alternatively, C _3-6 cycloalkyldithio or the like is used. The aryldithio group preferably includes an aryldithio group having 6 to 14 carbon atoms,
For example, C _6-14 aryldithio such as phenyldithio and naphthyldithio is used.

The aralkyldithio group is preferably an aralkyldithio group having 7 to 19 carbon atoms.
For example, phenyl-C _1-4 alkyldithio (eg, benzyldithio, phenethyldithio, etc.) and the like are used. The alkylsulfinyl group is preferably a straight-chain, branched or cyclic alkylsulfinyl group having 1 to 6 carbon atoms, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-hexylsulfinyl. And C _1-6 alkylsulfinyl such as cyclohexylsulfinyl and C _3-6 cycloalkylsulfinyl. The alkenylsulfinyl group is preferably a straight-chain, branched or cyclic alkenylsulfinyl group having 2 to 6 carbon atoms, for example, allylsulfinyl and the like. The arylsulfinyl group is preferably an arylsulfinyl group having 6 to 14 carbon atoms, such as phenylsulfinyl. The aralkylsulfinyl group is preferably an aralkylsulfinyl group having 7 to 19 carbon atoms, for example, phenyl-C _1-4 alkylsulfinyl (eg, benzylsulfinyl) and the like. Heterocyclic - sulfinyl group, a group represented by the formula T'-SO- (T 'is as defined heterocyclic group in R ³ described above) include groups represented by, specifically, 2- or Pyrrolylsulfinyl such as 3-pyrrolylsulfinyl and 3-, 4
Pyrazolylsulfinyl such as-or 5-pyrazolylsulfinyl and the like are used. The alkylsulfonyl group is preferably a linear, branched or cyclic alkylsulfonyl group having 1 to 6 carbon atoms, such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, and cyclohexylsulfonyl. C _1-6 alkylsulfonyl or C _3-6 cycloalkylsulfonyl is used. The alkenylsulfonyl group is preferably a straight-chain having 2 to 6 carbon atoms,
Examples thereof include a branched or cyclic alkenylsulfonyl group, for example, allylsulfonyl and the like. The arylsulfonyl group preferably has 6 to 14 carbon atoms.
And, for example, phenylsulfonyl, naphthylsulfonyl and the like are used. The aralkylsulfonyl group is preferably an aralkylsulfonyl group having 7 to 19 carbon atoms, for example, phenyl-C _1-4 alkylsulfonyl (eg, benzylsulfonyl, phenethylsulfonyl, phenylpropylsulfonyl group, etc.) and the like are used. . Examples of the heterocyclic-sulfonyl group include groups represented by the formula T′—SO ₂ — (T ′ has the same meaning as the heterocyclic group for R ³ described above),
Specific examples include pyrrolylsulfonyl such as 2- or 3-pyrrolylsulfonyl, and pyrazolylsulfonyl such as 3-, 4- or 5-pyrazolylsulfonyl.

Formula

Embedded image The group represented by is specifically an alkylamino group, preferably a mono- or di- (alkyl having 1 to 6 carbons) amino group (for example, methylamino, ethylamino,
n-propylamino, n-butylamino, tert-butylamino, n-pentylamino, n-hexylamino, dimethylamino, diethylamino, methylethylamino, di-
(N-propyl) amino, di- (n-butyl) amino and the like, a cycloalkylamino group, preferably a mono- or di (cycloalkyl having 3 to 6 carbon atoms) amino group (for example, cyclopropylamino, cyclopentylamino, Cyclohexylamino, dicyclohexylamino, etc.),
An arylamino group, preferably an arylamino group having 6 to 14 carbon atoms (for example, N-C _1-6 alkyl- _{NC 6-14} arylamino such as anilino and N-methylanilino), an aralkylamino group, preferably An aralkylamino group having 7 to 19 carbon atoms (for example, benzylamino,
Phenyl-C _1-4 alkylamino such as 1-phenylethylamino, benzhydrylamino, tritylamino, etc.), and acylamino groups, ie, of the formula T ″
T ″ ′ N— (T ″ is the above-mentioned acyl group, T ″ ″ is the same as the hydrogen atom, the above-mentioned hydrocarbon group or the acyl group for R ³ , and T ″ and T ′ ″ May form a ring together with the nitrogen atom), specifically, acetamido, propionamido, butyrylamino, pentanoylamino, hexanoylamino, succinimide, benzylcarbonylamino, phenethylcarbonylamino,
Benzoylamino, naphthoylamino, phthalimide,
C _1-6 alkylcarbonylamino groups such as thienylcarbonylamino and benzothienylcarbonylamino, C _6-14
An arylcarbonylamino group or a heterocyclic-carbonylamino group (here, alkyl, aryl, and heterocyclic groups are preferably the same as those exemplified for the substituent of the heterocyclic group for Q above) and the like are used. Where R ⁴ and R
⁵ may form a ring with adjacent nitrogen atoms,
Preferably, a 3- to 7-membered ring (for example, pyrrolidino, piperidino, morpholino, thiomorpholino, 1-piperazinyl, aziridino, azetidino, etc.) may be formed.

Formula

Embedded image The group represented by is specifically a mono- or di-alkylsulfamoyl group, preferably a mono- or di- (alkyl having 1 to 6 carbons) sulfamoyl group (for example, methylsulfamoyl, ethylsulfamoyl, n -Propylsulfamoyl, n-hexylsulfamoyl, dimethylsulfamoyl, diethylsulfamoyl, methylethylsulfamoyl, di- (n-butyl) sulfamoyl, etc.), cycloalkylsulfamoyl group, preferably carbon A cycloalkylsulfamoyl group having the number 3 to 6 (eg, cyclopropylsulfamoyl, cyclohexylsulfamoyl, etc.), an arylsulfamoyl group, preferably an arylsulfamoyl group having 6 to 14 carbon atoms (eg, phenyl) Sulfamoyl, etc.), aralkyl sulfamoyl group, Ku is from 7 carbon atoms 19
Aralkylsulfamoyl group (for example, phenyl-C _1-4 alkylsulfamoyl such as benzylsulfamoyl, benzhydrylsulfamoyl, tritylsulfamoyl and the like), acylsulfamoyl group,
Groups represented by the formula T ″ T ′ ″ NSO ₂ — (each symbol has the same meaning as described above) (for example, C _1-6 alkylcarbonylsulfamoyl group such as acetylsulfamoyl, benzylcarbonylsulfone Phenyl-C _1-4 such as famoyl
And a heterocyclic-carbonylsulfamoyl group such as an alkylcarbonylsulfamoyl group and a thienylcarbonylsulfamoyl group. Here, R ⁴ and R ⁵ may form a ring (for example, pyrrolidino, morpholino, thiomorpholino, 1-piperidinyl, aziridino, azetidino, etc.) together with an adjacent nitrogen atom.

The group represented by the formula R ⁵ —SO ₂ —O— is specifically an alkylsulfonyloxy group, preferably an alkylsulfonyloxy group having 1 to 6 carbon atoms (for example, methanesulfonyloxy, ethanesulfonyl) Oxy), an arylsulfonyloxy group, preferably an arylsulfonyloxy group having 6 to 14 carbon atoms (for example,
Benzenesulfonyloxy group, etc.), aralkylsulfonyloxy group, preferably an aralkylsulfonyloxy group having 7 to 19 carbon atoms (for example, phenyl-C such as benzylsulfonyloxy, phenethylsulfonyloxy, etc.)
_1-4 alkylsulfonyloxy group, etc.), acyl sulfonyloxy group (e.g., acetyl sulfonyloxy, such as C _1-6 alkylcarbonyl sulfonyloxy group such as butyryl sulfonyloxy) is used. As the substituent of the heterocyclic group for Q, a halogen atom, an alkyl group, an alkoxycarbonyl group, and an alkylsulfonyl group are preferable. The number of such substituents is 1-3, preferably 1-2. Examples of the hydrocarbon group represented by Q and its substituents include the same hydrocarbon groups and substituents as those exemplified for the above-mentioned organic residue. Among these hydrocarbon groups, an aralkyl group is particularly preferred. As the substituent of the aralkyl group, an alkanoyl group is particularly preferable. The number of the substituents is 1 to 3, preferably 1 to 2.

The alkyl group represented by R ¹ and R ² is preferably a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms, for example, methyl, ethyl, n-propyl,
Isopropyl, n-butyl, isobutyl, sec-butyl,
Tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, cyclopentyl, n-hexyl, isohexyl, cyclohexyl, etc. are used, and the alkoxy group is preferably a linear or branched alkoxy group having 1 to 6 carbon atoms. Means, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, n-hexyloxy, etc. are used, and the halogen atom is fluorine, chlorine , Bromine, iodine and the like are used. R ¹ and R ² are more preferably each a lower alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, n-butyl, te)
An alkyl group having 1 to 4 carbon atoms such as rt-butyl) or a lower alkoxy group (eg, an alkoxy group having 1 to 4 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy) Or a halogen atom (eg, fluorine, chlorine, bromine, iodine). More preferably, R ¹ and R ² are each a methyl group, a methoxy group or chlorine. Most preferably 1 to 1 carbon atoms such as methoxy
4 is an alkoxy group. W is preferably O. Z
Is preferably CH. As the compound (I), especially N
-(2-chloroimidazo [1,2-a] pyridine-3-
Ylsulfonyl) -N ′-(4,6-dimethoxy-2-
Pyrimidinyl) urea (imazosulfuron), N- (2-
Ethylsulfonylimidazo [1,2-a] pyridine-3
-Ylsulfonyl) -N '-(4,6-dimethoxy-2-
Pyrimidinyl) urea (sulfosulfuron), methyl = α
-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl) -O-toluate (bensulfuronmethyl), ethyl = 5- (4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl) -1- Methylpyrazole-4-carboxylate (pyrazosulfuronethyl) is preferred. The compound represented by the formula (I) or a salt thereof may be used alone, or two or more kinds may be used in combination.

Compound (I) is an acidic group in the molecule

Embedded image And an inorganic base salt or an organic base salt with an acidic group such as a sulfo group or a carboxyl group in a substituent, and a basic group such as a basic nitrogen atom in a molecule and an amino group in a substituent. Groups can form inorganic acid addition salts and organic acid addition salts. Examples of the inorganic base salt of compound (I) include salts with alkali metals (eg, sodium, potassium, etc.), alkaline earth metals (eg, calcium, etc.), ammonia, etc. Examples of the organic base salts of compound (I) include: Salts with dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2-phenylethylbenzylamine, benzylamine, ethanolamine and the like are used. Examples of the inorganic acid addition salt of compound (I) include salts with hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like, and examples of the organic acid addition salt of compound (I) include p-toluenesulfonic acid and methane Salts with sulfonic acid, formic acid, trifluoroacetic acid and the like are used. Compound (I) or a salt thereof is disclosed in JP-A-1-38091, JP-A-57-1.
It can be produced by the method described in JP-A-12379 or JP-A-59-219281 or a method analogous thereto.

The agricultural chemical preparation of the present invention may contain either a polycarboxylic acid surfactant or a formalin condensate of an aromatic sulfonic acid derivative or a salt thereof.
Polycarboxylic acid surfactants are particularly preferably used. The polycarboxylic acid-based surfactant is a polymer having a molecular weight of about 1,000 to 50,000 having a carboxylic acid as a structural unit, (1) an ethylenically unsaturated monocarboxylic acid polymer, and (2) an ethylenically unsaturated monocarboxylic acid. And a copolymer of ethylenically unsaturated dicarboxylic acid or its anhydride,
(3) Ethylene unsaturated monocarboxylic acid or copolymer of ethylene unsaturated dicarboxylic acid or anhydride and C _2-6 alkene, (4) Ethylene unsaturated monocarboxylic acid or ethylenically unsaturated dicarboxylic acid Or a copolymer of an anhydride thereof with an aromatic vinyl compound, and a salt thereof with an alkali metal (eg, sodium, potassium, etc.), an alkaline earth metal (eg, calcium, etc.), ammonia or an amine. . Examples of the ethylenically unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, crotonic acid and the like. Examples of the ethylenically unsaturated dicarboxylic acid include maleic acid, fumaric acid, and itaconic acid. Examples of the C _2-6 alkene include ethylene, propene, butylene, isobutylene, diisobutylene and the like. Examples of the aromatic vinyl compound include styrene, α-methylstyrene, vinyltoluene, and p-methylstyrene. Specifically, for example, polyacrylic acid, a copolymer of acrylic acid and maleic acid, a copolymer of isobutylene and maleic anhydride, a copolymer of acrylic acid and itaconic acid, a copolymer of methacrylic acid and itaconic acid , A copolymer of maleic acid and styrene, a copolymer of maleic acid and diisobutylene, and the like, and alkali metals (eg, sodium, potassium, etc.), alkaline earth metals (eg, calcium, etc.), ammonia or amine Salts. More specifically, Isoban 600SF35 (salt of isobutylene and maleic anhydride copolymer; Kuraray Co., Ltd.), Toxanone GR31A (Sanyo Chemical Co., Ltd.),
BOYS 530 (polyacrylate), BOYS 532A
(Ammonium polyacrylate) and BOISE 520 or 521 (copolymer salt of acrylic acid and maleic acid)
(Kao Corporation), New Cargen WG-5 (copolymer of maleic acid and alkene (molecular weight: 7000 to 8000; Takemoto Oil & Fats Co., Ltd.)) and the like. A copolymer of a saturated dicarboxylic acid or its anhydride and a C _2-6 alkene is preferred.

Examples of the formalin condensate of an aromatic sulfonic acid derivative or a salt thereof include phenyl, aryl-substituted phenyl, phenol, aryl-substituted phenol,
Examples include formalin condensates of sulfonic acid derivatives (eg, sulfonates) such as naphthalene, alkyl-substituted naphthalene, aralkyl-substituted naphthalene, anthracene, and alkyl-substituted anthracene or salts thereof. The aryl of the aryl-substituted phenyl or aryl-substituted phenol includes C _6-14 aryl such as phenyl and naphthyl. The number of substitutions is 1-3. Examples of the alkyl of the alkyl-substituted naphthalene include methyl, ethyl, n-propyl,
Isopropyl, n-butyl, isobutyl, sec-butyl, te
C _1-6 alkyl such as rt-butyl. The number of substitutions is one to seven. The aralkyl of the aralkyl-substituted naphthalene includes phenyl-C _1-4 alkyl such as benzyl, phenethyl and phenylpropyl, benzhydryl, trityl and the like. The number of substituents is 1-3. Examples of the alkyl of the alkyl-substituted anthracene include methyl, ethyl, n-propyl, isopropyl, n-butyl,
C _1-6 alkyl such as isobutyl, sec-butyl, tert-butyl and the like can be mentioned. The number of substituents is 1 to 9. The degree of condensation of such an aromatic sulfonic acid derivative with formalin is from 1.2 to 30, preferably from 1.2 to 10. Among the above, a formalin condensate of a naphthalene sulfonate is preferred. Examples of the salt include an alkali metal such as sodium, calcium, and ammonium, an alkaline earth metal, an ammonium salt, and the like. As a formalin condensate of an aromatic sulfonic acid derivative or a salt thereof, preferably, Neucalgen 9131 (formalin condensate of phenylphenol sulfonic acid; Takemoto Yushi Co., Ltd.), Labelin FM-L (formalin condensate of β-naphthalene sulfonic acid sodium) Products; Daiichi Kogyo Co., Ltd.), New Calgen WG
-2 (formalin condensate of β-naphthalenesulfonic acid sodium; Takemoto Yushi Co., Ltd.), Demol N (formalin condensate of β-naphthalenesulfonic acid sodium; Kao Corporation),
Demol C (formalin condensate of special aromatic sodium sulfonate; Kao Corporation) and the like are used. As the lignin sulfonate, sodium lignin sulfonate (eg,
Sun Extract P252 (Sanyo Kokusaku Pulp Co., Ltd.), New Calgen WG-4 (Takemoto Oil & Fats Co., Ltd.), calcium ligninsulfonate [eg, Sun Extract P201 (Sanyo Kokusaku Pulp Co., Ltd.), etc.], Lignin sulfone Alkali metal salts, alkaline earth metal salts, ammonium salts and the like of ligninsulfonic acid such as ammonium acid. Particularly, sodium ligninsulfonate is preferred.

The water-dispersible granules of the present invention may further contain one or more other pesticidal active ingredients in addition to the compound (I) or a salt thereof. For example, herbicides, insecticides, fungicides, acaricides, plant growth regulators, nematicides, attractants, repellents and the like are used. Above all, herbicides, insecticides, and fungicides are preferably used. One or more such pesticidal active ingredients can be used as a mixture with the compound (I) or a salt thereof. Herbicides, insecticides and fungicides may also include acaricides (eg, chlorbenzilate),
Plant growth regulators (eg, paclobutrazol), nematicides (eg, benomyl), synergists (eg, piperonyl butoxide), attractants (eg, eugenol),
Repellents (eg, creosote, etc.), pigments (eg, Food Blue No. 1, etc.), fertilizers (eg, urea, etc.) may be appropriately mixed.

Examples of the herbicides include the following (i) to
(xiv) and the like are used. (i) phenoxy herbicides such as 2,4-D, MCP
A, MCPCA, MCPB, chlomepro
p), naproanilide, etc. (ii) diphenyl ether herbicides such as chlornitrofen, chloromethoxynil (chlome
thoxynil), bifenox, cyhalofop-butyl, etc. (iii) Carbamate herbicides, such as swep (swe
p), thiobencarb, esprocarb (es
procarb), molinate, dimepiperate (dim
epiperate), pyributicarb, etc. (iv) acid amide herbicides, for example, propanil (propani
l), butachlor, pretilachlor (pret
(ilachlor), bromobutide (bromobutide), mefenacet (mefenacet), etobenzanide (etobenzanid), tenylchlor (thenylchlor), etc. (cinosulfuron), azimsulfuron,
Cyclosulfamuron, ethoxysulfuron, etc. (vii) Triazine herbicides, for example, simethrin (sime
tryn), prometryn (prometryn), dimethamethrin (dim
(viii) diazine herbicides such as bentazone (ben
(ix) diazole herbicide such as oxadiazone
(oxadiazon), pyrazolate (pyrazolate), pyrazoxyfen (pyrazoxyfen), benzofenap (benzofenap)
(X) dinitroaniline herbicides, such as trifluralin (xi) fatty acid herbicides, such as dalapon (xii) organophosphorus herbicides, such as piperophos (pipero
phos), etc. (xiii) nitrile herbicides such as chlorthiamide (c
hlorthiamid) (xiv) Other herbicides such as dithiopyr
r), cafenstrole, etc.

As the insecticides, for example, (i) to (i)
v) As the bactericide, for example, (v) to (xiii) are used. (i) organophosphorus insecticides such as fenthione
on), fenitrothion, pirimiphos-methyl, diazinon,
Quinalphos, isoxathione
n), pyridaphenthion, chlorpyrifos-methyl, vamidthione (v
amidothion), malathion, fentate
(phenthoate), dimethoate, disulfoton, monocrotophos, tetrachlorvinphos, chlorfenvinphos, propaphos
s), acephate, salithione
n), trichlorphon, EPN, pyraclofos, etc. (ii) Carbamate insecticides such as carbaryl
baryl), metolcarb, isoprocarb (is
oprocarb) (MIPC), BPMC, propoxur (prop)
oxur), xylylcarb, XMC, carbosulfan, benfuracar
(iii) synthetic pyrethroid insecticides such as cycloprothrin, ethofenprox (eth)
(iv) Other insecticides, for example, cartap,
Thiocyclam, bensultap
p), buprofezin, carbofuran (carbo
furan), furathiocarb (furathiocarb), cyanofenphos (cyanofenphos), nitenpyram (nitenpyram) and the like (v) polyhaloalkylthio fungicides, for example, captan (captan) such as Husaride
(fthalide), monguard, etc. (vii) Organophosphorus fungicides such as edifenphos (ed
ifenphos), IBP (iprobenfos), etc. (viii) Benzimidazole fungicides such as thiophanate-methyl, benomyl
(ix) Carboxamide fungicides such as mepronil
(mepronil), flutranil (flutolanil), tecloftalam (tecloftalam), pencyclone (pencycuron) and the like (x) acylalanine fungicides, for example, metalaxyl
(xi) N-heterocyclic ergosterol inhibitors, such as, for example, triflumizole, (xii) antibiotic fungicides, for example, kasugamycin (ka
sugamycin), validamycin A and the like. (xiii) Other fungicides such as probenazole (pro
benazole), isoprothiolane, tricyclazole, pyroquilon
n), oxolinic acid, ferimzone
(ferimzon), iprodione, etc.

The agrochemical preparation of the present invention may contain a carrier. Examples of such a carrier include an insoluble carrier and a water-soluble carrier which are solid at ordinary temperature. Examples of the insoluble carrier include, for example, vegetable powders (eg, soybean powder, tobacco powder, flour, wood powder, etc.), mineral powders (eg, clays such as kaolin, bentonite, acid clay, talc powder, lauric powder, etc.). Talc, diatomaceous earth, silica such as mica powder, etc.), alumina, sulfur powder, activated carbon, etc., among which diatomaceous earth is preferred. More specifically, as a dried product, for example, Radiolite SPF (trade name, manufactured by Showa Chemical Industry) or the like, and as a baked product, for example, Radiolite # 100, Radiolite # 200, Radiolite # 500, Radio Lite # 800, Radio Lite Fine Flow B (trade name, manufactured by Showa Kagaku Kogyo), and the like. 2000 (trade name, manufactured by Showa Chemical Industry Co., Ltd.) or the like is used. Above all, the specific surface area is 1-10
m ² / g of diatomaceous earth (e.g., the above fired product, a flux fired product, etc.) are preferable.

Examples of the water-soluble carrier include water-soluble neutral substances (eg, lactose, ammonium sulfate, urea, etc.),
A water-soluble weakly basic substance (for example, sodium bicarbonate, sodium thiosulfate, disodium hydrogen phosphate, sodium acetate, sodium carbonate, etc.) having a solubility in water at 20 ° C. of 0.05 g / ml or more and an aqueous solution at 25 ° C.
H is about 7 to 9, regardless of the presence of bound water)
And the like, and among them, lactose is preferred. Lactose can be used in any of the Japanese Pharmacopoeia, industrial use, food additives and the like. Further, those having an average particle diameter in the range of about 0.1 to 50 μm are preferable, and
Those having a size in a range of from 20 μm to 20 μm are preferable. If the particle size is larger than this range, fine particles may be mixed when formulated into a wettable powder, and it may be difficult to mold at the time of extrusion molding, so that means such as sieving after the formulation may be required. is there. If the particle size is smaller than this range, the mixing operation may be difficult. In the agricultural chemical preparation of the present invention, one or more of these carriers can be used.

In the pesticidal preparation of the present invention, in addition to the above-mentioned components, additives used in ordinary water dispersible granules can be used. For example, surfactants, binders, stabilizers, coloring agents, preservatives, and the like can be used freely, and these may be selected according to the type of the pesticidal active ingredient used. Examples of the surfactant include ordinary nonionic surfactants, cationic surfactants, and anionic surfactants, and one or more of these may be used. Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene alkyl ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and block copolymer of ethylene oxide and propylene oxide. Products, higher fatty acid alkanol amides and the like are used. Examples of the cationic surfactant include an alkylamine salt and a quaternary ammonium salt. Examples of the anionic surfactant include alkenyl sulfonates, alkylaryl sulfonates, polystyrene sulfonates, higher alkyl aryl ether sulfates, higher alcohol sulfates, higher alkyl ether sulfates, and dialkyl sulfo succinates. Acid salts and alkali metal salts of higher fatty acids are used.

As the surfactant used in the agricultural chemical preparation of the present invention, a nonionic surfactant or an anionic surfactant is preferable among the above-mentioned surfactants. As the binder, for example, a water-soluble binder is preferably used. Such water-soluble binders include, for example, dextrin, polyvinyl alcohol, gum arabic, sodium alginate, polyvinylpyrrolidone, glucose,
Sucrose, mannitol, sorbitol and the like are used. As the coloring agent, for example, cyanine green G, Erio green B400, or the like is used. As the preservative, for example, butyl paraben, potassium sorbate and the like are used.

The content of the compound (I) or a salt thereof in the pesticide preparation of the present invention is usually about 1 to the whole preparation.
%, Preferably about 3 to 85% by weight, more preferably about 5 to 80% by weight. When pesticidal active ingredients other than compound (I) or a salt thereof are mixed in the pesticide preparation of the present invention, the content thereof is usually about 70 to 95% by weight, preferably about 75 to 85% by weight, based on the whole preparation. % By weight. The content of the polycarboxylic acid-based surfactant or the formalin condensate of the aromatic sulfonic acid derivative or the salt thereof is usually in the range of about 1 to 15% by weight, preferably about 1 to 10% by weight based on the whole preparation. . The content of the lignin sulfonate is generally used in the range of about 1 to 15% by weight, preferably about 1 to 10% by weight based on the whole preparation. The content of the carrier, for example, lactose, ammonium sulfate, sodium bicarbonate or diatomaceous earth, is usually 0 to about 30% by weight, preferably about 5 to 25% by weight, but depends on the concentration of the active ingredient, surfactant and the like in the preparation. It can be changed accordingly.
The surfactant is usually used in an amount of about 0.1 to 1 based on the whole preparation.
It is used in an amount of 5% by weight, preferably 0.1 to 10% by weight. The binder is used usually in the range of 0 to 20% by weight, preferably 0 to 10% by weight, based on the whole preparation.
The coloring agent is usually 0 to 0.5% by weight based on the whole preparation,
Preferably, it is used in the range of 0 to 0.3% by weight. The preservative is used in an amount of usually 0.1 to 5% by weight, preferably 0.1 to 3% by weight, based on the whole preparation.

[0034]

BEST MODE FOR CARRYING OUT THE INVENTION The wettable powder of the present invention can be produced by mixing and granulating each component. The pesticidal active ingredient is preferably finely pulverized for dispersibility and suspension stability when diluted with water. Examples of the pulverization method of each component include dry pulverization and wet pulverization. For example, in the case of performing dry pulverization, (1) only agrochemical active ingredients are pulverized in advance with a pulverizer such as an impact pulverizer or a jet mizer, and then (a) formalin of a polycarboxylic acid-based surfactant or an aromatic sulfonic acid derivative. A condensate or a salt thereof, (b) a lignin sulfonate and, if desired, (c) a carrier or an additive are mixed in a predetermined amount, or (2) (a) a pesticidal active ingredient is mixed with
(b) a formalin condensate of a polycarboxylic acid-based surfactant or an aromatic sulfonic acid derivative or a salt thereof, (c) a lignin sulfonate and, if desired, (d) a predetermined amount of a carrier and additives are uniformly mixed, The mixture obtained by the above (1) or (2) may be pulverized by a pulverizer such as an impact type pulverizer or a jet miser, and an appropriate amount of water may be added to perform wet granulation. Granulation can be performed by an extrusion granulator, a rolling granulator, a fluidized bed granulator, etc., but it is preferable to granulate by an extrusion granulator from the viewpoint of simplicity of operation, productivity and the like. . For example, when performing wet pulverization, an appropriate amount of water (10
(30 parts to 800 parts by weight, based on 0 parts by weight of the solid content of the preparation), the (a) agrochemical active ingredient and (b) a formalin condensate of a polycarboxylic acid surfactant or an aromatic sulfonic acid derivative or a salt thereof. , (C) a predetermined amount of lignin sulfonate and optionally (d) carrier and other additives, ball mill,
Sand grinder, pulverize with a pulverizer such as a dyno mill, then add the appropriate amount of other carriers and additives as needed to the resulting aqueous suspension, mix and spray dry granulate with a spray dryer etc. Good. When it is desired to further increase the average particle size of the granules thus obtained, an appropriate amount of water may be further added and wet granulation similar to the above may be performed. The average particle diameter of the wettable powder of the present invention is preferably about 0.1 to 5 mm, particularly preferably about 0.3 to 2 mm. The bulk density of the thus obtained wettable powder of the present invention is usually preferably in the range of about 0.1 to 1.2 g / ml, particularly preferably about 0.5 to 1.0 g / ml. Is preferable. Since the pesticide formulation of the present invention uses safe ingredients, it is practically free of phytotoxicity to plants, and harmless to humans and animals during or after application, and is used as a safe formulation. be able to. In addition, the agricultural chemical formulation of the present invention has good disintegration in water and excellent water dispersibility.

Examples of the application object include rice and wheat (eg,
Wheat, barley), beetroot, corn, cotton, vegetables (eg, cabbage, Chinese cabbage, radish, cucumber, eggplant, potato), fruit trees (eg, tangerine, peach, none),
Paddy fields, fields, orchards, turf, non-agricultural lands, etc. where tea, tobacco, etc. are grown.

The amount of the pesticide preparation of the present invention varies depending on the kind and content of the pesticidal active ingredient contained therein, the place of application, the kind of the target pest, and the like. , Potatoes, cotton, etc.), orchards, turf, etc. About 10-40 per 10 ares
0 g, preferably about 20-300 g. The amount of the compound (I) or a salt thereof, which is an active ingredient, is about 1 to 10 per are, such as the paddy field, the field, the orchard, and the turf.
150 g, preferably about 3-100 g. A known method generally used for spraying pesticides can be used. For example, the pesticide granule of the present invention is used as it is or diluted with water before spraying. For example, about 100 to 20000 times (about 1 g / 100 ml
(1 g / 20,000 ml). As the method of spraying, the same method as that for a normal wettable powder for granules can be used, and examples thereof include aerial spraying, soil spraying, foliage spraying, nursery box spraying, lateral streak application, and seed treatment. The pesticide preparation of the present invention is preferably stored in a moisture-proof container or the like to avoid moisture. As such containers, for example, plastic bottles, polyethylene bottles, polyethylene-laminated aluminum foil packaging, polyethylene bags, and the like are simple.

[0037]

EXAMPLES The present invention will be described below in detail with reference to examples, but the present invention is not limited to these examples.

[0038]

Example 1 80 parts of imazosulfuron previously ground to a mean particle size of 5 μm or less with a jet miser (PJM-100NP type from Nippon Pneumatic Industries, Ltd.) and lignin sulfonate [San Extract P252: Sanyo Kokusaku Pulp Co., Ltd.] 6 parts, polycarboxylate [Newcalgen WG
-5: Takemoto Yushi Co., Ltd.] 4 parts, and lactose [VALIO] 1
0 parts were uniformly mixed in a mortar, and 15 parts of water was added and kneaded. Then, the kneaded material is sieved with a granulator [Kikusui Seisakusho Co., Ltd.
RG-5M type] using a 0.5 mmφ screen, extrusion granulation, drying at 60 ° C. for 1 hour, and a grain length of about 1 to 3 mm
Granules were obtained.

[0039]

Example 2 Formalin condensate of 80 parts of imazosulfuron and sodium naphthalenesulfonate [New Cargen WG-2: Takemoto Yushi Co., Ltd.] 5 parts, lignin sulfonate [San Extract P252: Sanyo Kokusaku Pulp Co., Ltd.] 5
Parts and Radiolight # 200 (diatomaceous earth: Showa Chemical Industry Co., Ltd.) were uniformly mixed in a mortar, and kneaded by adding 15 parts of water. Thereafter, the kneaded product was extruded and granulated using a 0.5 mmφ screen with a granulator (RG-5M, manufactured by Kikusui Seisakusho Co., Ltd.), dried at 60 ° C. for 1 hour, and the grain length was about 1 to 3 mm. Granules were obtained.

[0040]

[Comparative Example 1] 80 parts of imazosulfuron previously ground to a mean particle size of 5 µm or less with a jet miser (PJM-100NP type, Nippon Pneumatic Industries, Ltd.) and lignin sulfonate [San Extract P252: Sanyo Kokusaku Pulp Co., Ltd. 4 parts, ammonium polyoxyethylene alkyl phenyl ether sulfate [Hytenol N-08: Daiichi Kogyo Seiyaku Co., Ltd.], and bentonite [Hodaka:
13 parts were uniformly mixed in a mortar and mixed with 15 parts of water.
And kneaded. Thereafter, the kneaded product was extruded and granulated using a 0.5 mmφ screen with a granulator (RG-5M type manufactured by Kikusui Seisakusho Co., Ltd.), and dried at 60 ° C. for 1 hour.
Granules having a length of about 1 to 3 mm were obtained.

[0041]

Comparative Example 2 Imazosulfuron (75 parts), which was previously ground to an average particle size of 5 μm or less with a jet miser (Nippon Pneumatic Industrial Co., Ltd., PJM-100NP type), and a polycarboxylate (Newcalgen WG-5: Takemoto Yushi Co., Ltd.) )] 7.
5 parts, 5 parts of alkyl phenyl ether ammonium sulfate [Newcalgen WG-7: Takemoto Yushi Co., Ltd.], 5 parts of ammonium sulfate [Ube Industries, Ltd.], and 7.5 parts of clay [Katsumitsuyama Mining] in a mortar. They were mixed and kneaded by adding 15 parts of water. Thereafter, the kneaded product was extruded and granulated using a 0.5 mmφ screen with a granulator (RG-5M, manufactured by Kikusui Seisakusho Co., Ltd.), dried at 60 ° C. for 1 hour, and the grain length was about 1 to 3 mm. Granules were obtained.

[0042]

Comparative Example 3 Formalin condensate of 75 parts of imazosulfuron and sodium naphthalenesulfonate (Newcargen WG-2: 7 parts of Takemoto Oil & Fat Co., Ltd., 3 parts of alkyl naphthalene sulfonate [New Cargen WG-1: Takemoto Oil & Fat Co., Ltd.], and 15 parts of clay [Katsumitsuyama Mining] are uniformly mixed in a mortar and 15 parts of water. And kneaded. Thereafter, the kneaded product was subjected to a granulator [RG-5M manufactured by Kikusui Seisakusho Co., Ltd.]
Extrusion granulation using a 0.5 mmφ screen with
After drying at 60 ° C. for 1 hour, granules having a particle length of about 1 to 3 mm were obtained.

[0043]

[Comparative Example 4] 80 parts of imazosulfuron, which was previously ground to a mean particle size of 5 µm or less with a jet mizer [PJM-100NP type, Nippon Pneumatic Industries, Ltd.], and an alkyl naphthalene sulfonate [New Calgen WG-1: Takemoto Yushi ( 2 parts) ammonium polyoxyethylene alkylphenyl ether sulfate [Newcalgen WG-7:
Takemoto Oil & Fat Co., Ltd.], tripolyphosphoric acid [Wako Pure Chemical Industries, Ltd.] 2 parts, sucrose [Wako Pure Chemical Industries, Ltd.] 3 parts, bentonite [Hotaka Ind. , And kneaded by adding 15 parts of water. Thereafter, the kneaded product was extruded and granulated with a granulator [RG-5M type manufactured by Kikusui Seisakusho Co., Ltd.] using a 0.5 mmφ screen,
C. for 1 hour to obtain granules having a grain length of about 1 to 3 mm.

[0044]

Test Example 1 Underwater Disintegration Test A 250 ml measuring cylinder was charged with 250 ml of 3rd degree hard water, and 0.1 g of a sample was charged. The disintegration and dispersibility of the sample were observed, and the dispersibility was evaluated according to the following three grades. ：: Most of the particles disintegrate and disperse before reaching the bottom of the measuring cylinder. Δ: While collapsing while pulling the yarn, particles with insufficient collapsing exist at the bottom of the measuring cylinder. ×: Reached the bottom of the measuring cylinder with almost no collapse.

[0045]

[Test Example 2] Dispersibility test in water 250 ml of 3rd hard water was put into a 250 ml measuring cylinder, 0.1 g of a sample was put into this cylinder, and after 15 seconds, the measuring cylinder was slowly turned over, and all the particles were completely disintegrated and completely disintegrated. The number of inversions until dispersing was expressed as dispersibility in water.
The results are shown in [Table 1].

[0036]

[Table 1]

[0037]

EFFECT OF THE INVENTION The water dispersible granule of the present invention can increase the content of the pesticidal active ingredient in the preparation, has good disintegration in water, and shows high dispersion stability.

Claims (11)

[Claims] (1) Formula (I): ## STR1 ## [In the formula, Q represents an optionally substituted heterocyclic group or an optionally substituted hydrocarbon group, W represents an oxygen atom or a sulfur atom, and R ¹ and R ² represent an alkyl group, an alkoxy group or a halogen, respectively. An atom, Z represents CH or N. Or a salt thereof; (2) a formalin condensate of a polycarboxylic acid surfactant or an aromatic sulfonic acid derivative or a salt thereof; and (3) a lignin sulfonic acid salt-containing water dispersible granule. 2. The compound represented by the formula [I] is N- (2-
The water dispersible granule according to claim 1, which is chloroimidazo [1,2-a] pyridin-3-ylsulfonyl) -N '-(4,6-dimethoxy-2-pyrimidinyl) urea. 3. The compound represented by the formula [I] is N- (2-
Ethylsulfonylimidazo [1,2-a] pyridine-3
-Ylsulfonyl) -N '-(4,6-dimethoxy-2-
2. The water dispersible granule according to claim 1, which is pyrimidinyl) urea. 4. The water dispersible granule according to claim 1, which further contains another pesticidal active ingredient in addition to the compound represented by the formula [I] or a salt thereof as the pesticidal active ingredient. 5. A compound represented by the formula [I] or a salt thereof, and 70 to 95% by weight of a total of other pesticidal active ingredients.
5. The water dispersible granule according to claim 4, which contains the powder. 6. A formalin condensate of a polycarboxylic acid-based surfactant or an aromatic sulfonic acid derivative or a salt thereof.
The water dispersible granule according to claim 4, which is contained in an amount of from 15 to 15% by weight. 7. The water dispersible granule according to claim 4, comprising 1 to 15% by weight of a lignin sulfonate. 8. The method according to claim 1, wherein the average particle size is 0.1 to 5 mm.
The water dispersible granules according to the above. 9. A compound represented by the formula [I] or a salt thereof, (2) a formalin condensate of a polycarboxylic acid surfactant or an aromatic sulfonic acid derivative or a salt thereof,
2. The method for producing a water-dispersible granule according to claim 1, wherein (3) lignin sulfonate is mixed and granulated. 10. The use of the wettable powder according to claim 1, which is applied to paddy fields, fields, orchards, turf or non-agricultural lands. 11. The method according to claim 10, wherein the water dispersible granule according to claim 1 is diluted 100 to 20,000 times with water before spraying.