JP3462247B2 - Carbohydroxymoylazole derivatives and insecticides - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a carbohydroxymoylazole derivative having a 5-membered heterocyclic ring and a condensed heterocyclic ring, and an insecticide containing the same as an active ingredient.

[0002]

2. Description of the Related Art Regarding carbohydroxymoylazole derivatives of alkanecarboxylic acids or cycloalkanecarboxylic acids, the bactericidal activity of pivalic acid derivatives is known in US Pat. No. 4,599,348.

[0003]

Problems to be Solved by the Invention US Pat. No. 4,599,934
Nothing is known about the insecticidal activity of the compounds described in the specification of Japanese Patent No. 8 publication. Further, a carbohydroxymoylazole derivative having a 5-membered heterocyclic ring or a condensed heterocyclic ring has not been known so far.

On the other hand, in recent years, the existing pesticides have also become less effective due to the generation of resistant pests due to long-term use. In particular,
Hemiptera pests such as planthoppers, leafhoppers, aphids and stink bugs cause great damage to agricultural crops such as rice, wheat and potato and trees. Also, many hemiptera pests show resistance to existing insecticides,
It is becoming a global problem. Therefore, there is a demand for the development of an insecticide that has high efficacy even at a low dose, is highly safe, and is useful for resistant pests.

[0005]

The inventor has found that various complex 5
A carbohydroxymoylazole derivative having a membered ring or a condensed heterocycle was synthesized and its physiological activity was investigated. As a result, it was found that the compound of the present invention has extremely excellent insecticidal activity against various harmful insects, especially susceptible and resistant planthoppers and leafhoppers, aphids and stink bugs, and other hemiptera pests. The invention has been completed.

That is, the present invention has the general formula [I]

[0007]

[Chemical 3] (Where A is the formula

[0008]

[Chemical 4] Represents a heterocycle represented by R is a C ₁ -C ₆ alkyl group, a C ₁ -C ₆ haloalkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₂ -C ₆ alkenyl group, a phenyl group, a benzyl group, A C ₁ -C ₆ acyl group, a naphthylcarbonyl group, a benzoyl group, a C ₁ -C ₆ alkoxycarbonyl group, a carbamoyl group, an N-C ₁ -C ₆ alkylcarbamoyl group,
C ₁ -C ₆ alkylsulfonyl group, phenylsulfonyl _group, C 1 -C ₆ alkoxy _C 1 -C ₆ alkyl group, _{C 1}
To C ₆ alkylthio C _{1 to} C ₆ alkyl group, furancarbonyl group, thiophenecarbonyl group, pyridylcarbonyl group, optionally substituted pyridyl group or pyrimidinyl group, R ¹ is hydrogen atom, C _{1 to} C ₆ alkyl group , Phenyl group or benzyl group, X is a hydrogen atom, C ₁
To C ₈ alkyl group, C _{3 to} C ₆ cycloalkyl group, C ₃
-C ₆ cycloalkyl _C 1 -C ₆ alkyl _group, C 3 -C
₆ cycloalkenyl group, C ₁ -C ₈ haloalkyl group, C
₁ -C ₈ alkoxy group, trimethylsilyl group, trimethylsilyl _C 1 -C ₆ alkyl group, a trimethylsilyl _{C 1}
To C ₆ alkoxy group, trimethylsilyl C _{2 to} C ₆ alkynyl group, C _{2 to} C ₈ alkenyl group, C _{2 to} C ₈ alkynyl group, phenyl group, benzyl group, optionally substituted phenoxy group, cyclohexenylidene C ₁ To C ₆ alkyl group, a halogen atom or an optionally substituted phenylthio group, W represents a nitrogen atom or a methine group, and n is 1
Indicates an integer of ˜3. ), And a pesticide containing the same as an active ingredient.

In the present invention, the halogen atom is
Examples thereof include chlorine atom, bromine atom, fluorine atom and iodine atom. As the C ₁ -C ₈ alkyl group, a linear or branched alkyl group, for example, a methyl group,
Ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n
-Pentyl group, i-pentyl group, s-pentyl group, n-
Hexyl group, i-hexyl group, s-hexyl group, group CH
_{2 CH (CH 3) C 2} H 5, neo- pentyl group, group C
H ₂ CH (CH ₃ ) C ₃ H ₇ , group C ₂ H ₄ CH (C
H ₃ ) C ₂ H ₅ , the group CH ₂ CH (CH ₃ ) CH (C
H ₃ ) ₂ , n-heptyl group, i-heptyl group, s-heptyl group, n-octyl group, i-octyl group, s-octyl group and the like.

The C ₂ -C ₈ alkenyl group is a straight chain or branched alkenyl group, for example, an ethenyl group, a 2-propenyl group, a 1-methylethenyl group, a 1-butenyl group, a 2-butenyl group, 3- Butenyl group, 1-pentenyl group, 3,3-dimethyl-1-butenyl group, 1-hexenyl group, 1-heptenyl group, 1-octenyl group, 2
An octenyl group and the like. The alkynyl groups of C ₂ -C _8, linear or branched alkynyl group, e.g., 3,3-dimethyl-1-butynyl group,
1-octynyl group etc. can be mentioned.

Examples of the C ₁ -C ₈ haloalkyl group include chloromethyl group, chloroethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluoroisopentyl group, 4,4,4- Examples thereof include trifluoro-3,3-bis (trifluoromethyl) butyl group, 1-chloropropenyl group and 3-fluorooctyl group. As the C ₃ -C ₆ cycloalkyl group, for example,
Examples thereof include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and the like. Examples of the C _{1 to} C ₆ acyl group include an acetyl group, a propionyl group, a butyryl group, and a valeryl group.

The C ₁ -C ₈ alkoxy group is a linear or branched alkoxy group such as methoxy group, ethoxy group, propoxy group, isopropoxy group, isobutoxy group, s-butoxy group, t-butoxy group, i-
Pentyloxy group, neopentyloxy group, 1-methylbutoxy group, 2-methylbutoxy group, 1,2-dimethylpropoxy group, 2-ethylbutoxy group, 2,2-dimethylbutoxy group, 3,3-dimethylbutoxy group , 2, 3,
Examples thereof include a 3-trimethylpropoxy group, a heptyloxy group, an octyloxy group and the like.

A-1 is a 2-furyl group or a 3-furyl group, A-2 is a 2-thienyl group or a 3-thienyl group, and A-3 is a 2-pyrrolyl group or a 3-pyrrolyl group. , A-4 is 4-pyrazolyl group, A-5 is 2-benzofuranyl group, A-6 is 2-benzothiophenyl group, A-7 is 2-indolyl group,
Mention may be made of 6-indolyl groups.

Preferred compounds in the present invention are:
A represents a 2-furyl group, a 3-furyl group or a 2-thienyl group, X represents a halogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, and R represents an ethyl group, an i-propyl group or Examples thereof include a compound that represents an s-butyl group, W represents a nitrogen atom, and n represents an integer of 1 or 2.

The carbohydroxymoylazole derivative represented by the general formula [I] has two kinds of stereo isomers, a syn isomer and an anti isomer, but the present invention includes these isomers and any of these isomers. It also includes a mixture of ratios.

The compounds of the present invention represented by the general formula [I] are shown in Tables 1 to 34. Ph described in the table represents a phenyl group. The compound numbers will be referred to in the following description.

[0017]

[Table 1]

[0018]

[Table 2]

[0019]

[Table 3]

[0020]

[Table 4]

[0021]

[Table 5]

[0022]

[Table 6]

[0023]

[Table 7]

[0024]

[Table 8]

[0025]

[Table 9]

[0026]

[Table 10]

[0027]

[Table 11]

[0028]

[Table 12]

[0029]

[Table 13]

[0030]

[Table 14]

[0031]

[Table 15]

[0032]

[Table 16]

[0033]

[Table 17]

[0034]

[Table 18]

[0035]

[Table 19]

[0036]

[Table 20]

[0037]

[Table 21]

[0038]

[Table 22]

[0039]

[Table 23]

[0040]

[Table 24]

[0041]

[Table 25]

[0042]

[Table 26]

[0043]

[Table 27]

[0044]

[Table 28]

[0045]

[Table 29]

[0046]

[Table 30]

[0047]

[Table 31]

[0048]

[Table 32]

[0049]

[Table 33]

[0050]

[Table 34] The compound of the present invention can be produced by the following production methods A to C, but is not limited to these methods. Manufacturing method A

[0051]

[Chemical 5] (In the formula, D represents a halogen atom, a paratoluenesulfonyloxy group or a methanesulfonyloxy group, and A,
R and W have the same meanings as described above. ) That is, the compound of the present invention represented by the general formula [I] is
It can be produced by reacting the carbohydroxymoylazole compound represented by I] with the halogen compound or sulfonate compound represented by the formula [III] in the presence of a base. In this reaction, the halogen compound or the sulfonate compound can be used in an equivalent amount or more. Further, as a base that can be used, sodium hydride, alkali metal hydrides such as potassium hydride, sodium hydroxide, alkali metal hydroxides such as potassium hydroxide, sodium carbonate,
Inorganic bases such as alkali metal carbonates such as potassium carbonate, sodium hydrogen carbonate, alkali metal bicarbonates such as potassium hydrogen carbonate, or triethylamine, N, N
Examples include organic bases such as dimethylaniline, pyridine, and 1,8-diazabicyclo [5.4.0] unde-7-cene.

The reaction can be carried out in the presence of a suitable diluent if necessary. Diluents that can be used include water or inert organic solvents, for example, ketones such as acetone and butanone, aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene that may be halogenated, petroleum ether, ligroin, etc. Aliphatic hydrocarbons, ethers such as diethyl ether, tetrahydrofuran and dioxane, nitriles such as acetonitrile and propionitrile, and amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone Etc.

The reaction temperature is in the range of 0 ° C to the reflux temperature in the reaction system, preferably 40 ° C to 100 ° C.
Although the reaction time varies depending on the compound, the purpose can be reached in 1 to 6 hours.

The carbohydroxymoylazole compound represented by the general formula [II] can be produced by the method represented by the following reaction formula.

[0055]

[Chemical 6] (In the formula, E represents a halogen atom, and A and W have the same meanings as described above.) The carbohydroxymoylazole compound represented by the general formula [II] is the carbohydroxymoyl halide compound represented by the formula [IV]. Can be produced by reacting the imidazole or triazole represented by the formula [V] in the presence of a base. In this reaction, imidazole or triazole may serve as a base or a solvent and may be used in an equivalent amount or more. Further, as the base, the same base as described above can be used.

The reaction can be carried out in the presence of a suitable diluent if necessary. Examples of the diluent include the same diluents as described above. The reaction temperature is any temperature from room temperature to the reflux temperature in the reaction system, preferably 80
~ 130 ° C. The reaction time depends on the compound,
It may be allowed to react for 2 to 5 hours.

The carbohydroxymoyl halide compound represented by the general formula [IV] is obtained by reacting a corresponding aldoxime compound by a known method in the presence of N, N-dimethylformamide and a halogenating agent consisting of N-chlorosuccinimide. It can be produced by reacting. Manufacturing method B

[0058]

[Chemical 7] (In the formula, E represents a halogen atom, and A, R, and W have the same meanings as described above.) That is, the compound of the present invention represented by the general formula [I] is represented by the formula [V
It can be produced by reacting the carbohydroxymoyl halide compound represented by I] with the imidazole or triazole represented by the formula [V] in the presence of a base. In this reaction, imidazole or triazole may serve as a base or a solvent and may be used in an equivalent amount or more. Moreover, as the base, the same bases as described in the production method A can be used.

The reaction can be carried out in the presence of a suitable diluent if necessary. As the diluent, the same one as described in the production method A can be used.

The reaction temperature is in the range of room temperature to the reflux temperature in the reaction system, preferably 80 to 160 ° C. The reaction time varies depending on the compound, but the purpose can be reached in 2 to 15 hours.

The carbohydroxymoyl halide compound represented by the general formula [VI] can be produced by the method represented by the following reaction formula.

[0062]

[Chemical 8] (In the formula, A, E and R have the same meanings as described above.) The hydroxamic acid compound represented by the general formula [VII] is
React with a halogenating agent such as phosphorus pentachloride or thionyl chloride in the presence of an inert solvent such as aromatic hydrocarbons such as benzene and toluene or halogenated hydrocarbons such as chloroform and carbon tetrachloride, or acetonitrile. React with a halogenating agent consisting of triphenylphosphine and carbon tetrachloride or carbon tetrabromide in the presence of an inert solvent such as nitriles such as propionitrile or aromatic hydrocarbons such as benzene and chlorobenzene. It can be manufactured. In this case, carbon tetrachloride and carbon tetrabromide can also serve as a solvent. The reaction temperature is in the range of 0 ° C to the reflux temperature in the reaction system, preferably 50 to 80 ° C. The reaction time varies depending on the compound, but the reaction may be performed for 1 to 6 hours.

The hydroxamic acid compound represented by the general formula [VII] is prepared by converting the corresponding carboxylic acid by a known method.
It can be produced by preparing an acid halide or 1-acylimidazole and reacting it with an alkoxyamine. Manufacturing method C

[0064]

[Chemical 9] (In the formula, R ² represents an alkyl group, a trimethylsilyl group or a trimethylsilyl C ₁ -C ₄ alkyl group, and R,
A, E and W have the same meanings as described above. That is, the compound of the present invention represented by the general formula [I-1] is a carbohydroxymoylazo-compound represented by the formula [VIII].
In the presence of bis (triphenylphosphine) palladium (II) chloride as a catalyst and cuprous iodide as a catalyst, and a 1-alkyne of the formula [IX] in an amine such as diethylamine or triethylamine. Alternatively, it can be produced by reacting them in a mixed solvent of tetrahydrofuran and these.

The reaction temperature is in the range of 0 ° C. to the reflux temperature in the reaction system, preferably 20 to 100 ° C. The reaction time is 4 to 48 hours, and the purpose can be achieved.

[0066]

EXAMPLES Next, the production method of the compound of the present invention will be specifically explained with reference to examples. Production Example 1 1- (O-isopropyl-5-bromo-2-thiophenecarbohydroxymoyl) imidazole (Compound No. 2
86) Preparation of 1- (5-bromo-2-thiophenecarbohydroxymoyl) imidazole 1.8 g (6.6 mmol) was added to N,
It was dissolved in 50 ml of N-dimethylacetamide, 1.2 g (7.0 mmol) of potassium carbonate and 1.0 g (7.0 mmol) of 2-iodopropane were added, and the mixture was reacted at 70 ° C. for 3 hours. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous magnesium sulfate, the solvent is removed under reduced pressure, the residue is purified by column chromatography, and the melting point is 90.0-9.
1.2 g (yield 58%) of the target product at 2.0 ° C. was obtained. NMR data (60 MHz, CDCl ₃ solvent, σ value) 1.32 (d, 6H) 4.42 (quintet, 1H) 6.65 (q, 2H) 7.10 (d, 2H) 7.82 (s, 1H)

Production Example 2 Production of 1- (O-isopropyl-5-hexyl-3-furancarbohydroxymoyl) -1H-1,2,4-triazole (Compound No. 194) O-isopropyl-5-hexyl-3 -Furancarbohydroxymoyl chloride 0.8 g (3.0 mmol),
0.4 g of 1H-1,2,4-triazole (6.0 mm
ol) and 0.8 g (6.0 mmol) of potassium carbonate were added to 50 ml of N, N-dimethylacetamide to give 130
The mixture was heated and stirred at ~ 150 ° C for 8 hours. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, the residue was purified by column chromatography, and 0.7 g of the target product having a refractive index of 1.5122 at 20 ° C. (yield 78 %) Was obtained. NMR data (60 MHz, CDCl ₃ solvent, σ value) 0.67 to 0.95 (m, 3H) 1.00 to 1.90 (m, 8H) 1.24 (d, 6H) 2.34-2. 70 (m, 2H) 4.43 (quintet, 1H) 6.23 (s, 1H) 7.72 (s, 1H) 7.94 (s, 1H) 8.90 (s, 1H)

Production Example 3 1- (O-isopropyl-5- (3,3-dimethyl-1)
-Butynyl) -4-furancarbohydroxymoyl)-
1H-1,2,4-triazole (Compound No. 173)
Preparation of 1- (O-isopropyl-2-bromo-4-furancarbohydroxymoyl) -1H-1,2,4-triazole 1.7 g (6 mmol), 3,3-dimethyl-1-butyne 0.9 g ( 11 mmol), bis (triphenylphosphine) palladium (II) chloride (50 mg) and cuprous iodide (50 mg) were added to triethylamine (30 ml), and the mixture was stirred under reflux for 8 hours. The reaction mixture was filtered, the filtrate was concentrated, and the residue was extracted with ethyl acetate. The organic layer is dried over anhydrous magnesium sulfate, the solvent is removed under reduced pressure,
The residue is purified by column chromatography, melting point 53
1.4 g (yield: 82%) of the desired product having a temperature of ˜58 ° C. NMR data (60 MHz, CDCl ₃ solvent, σ value) 1.30 (s, 9H) 1.32 (d, 6H) 4.45 (quintet, 1H) 6.77 (s, 1H) 7.82 (s, 1H) 7.93 (s, 1H) 8.97 (s, 1H)

Production Example 4 Production of 1- (O-isopropyl-2-benzo [b] furancarbohydroxymoyl) -1H-1,2,4-triazole (Compound No. 654) O-isopropyl-2-benzo [b] ] Furancarbohydroxymoyl chloride 5.0 g (21 mmol), 1H
-1,2,4-triazole 7.0 g (0.1 mol)
And 4.0 g (0.1 mol) of sodium hydride in N,
Add to 100 ml of N-dimethylacetamide and add 150 ° C.
The mixture was heated and stirred for 8 hours. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with toluene. After washing the organic layer with water,
The extract was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, the residue was purified by column chromatography, and 1.1 g of the desired product having a melting point of 110.0 to 112.0 ° C (yield 1
9.4%).

Production Example 5 1- (O-isopropyl-3-chloro-2-benzo [b] thiophenecarbohydroxymoyl) -1H-
Preparation of 1,2,4-triazole (Compound No. 663) O-isopropyl-3-chloro-2-benzo [b] thiophenecarbohydroxymoyl chloride 13.8 g (4
7.9 mmol), 1H-1,2,4-triazole 7.0 g (0.1 mol) and sodium hydride 4.0.
g (0.1 mol) of N, N-dimethylacetamide 1
In addition to 00 ml, the mixture was heated with stirring at 150 ° C. for 5 hours. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with toluene. The organic layer was washed with water, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, the residue was purified by column chromatography, and 4.5 g of the desired product having a melting point of 122.0-124.0 ° C (yield 29.2%).

Production Example 6 Production of 1- (O-isopropyl-3-thiophenecarbohydroxymoyl) -1H-1,2,4-triazole (Compound No. 361) O-isopropyl-3-thiophenecarbohydroxymoyl chloride 15. 6 g (76.6 mmol), 1H-
7.0 g (0.1 mol) of 1,2,4-triazole and 4.0 g (0.1 mol) of potassium carbonate were added to 100 ml of N, N-dimethylacetamide, and 1
The mixture was heated and stirred for 5 hours. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with toluene. The organic layer is washed with water and dried over anhydrous magnesium sulfate, the solvent is removed under reduced pressure,
The residue is purified by column chromatography, melting point 4
5.7 g (yield 31.5) of the desired product at 3.5-44.5 ° C
%) Was obtained.

Production Example 7 1- [O-isopropyl-2- (1-methylpyrrole)
Preparation of Carbohydroxymoyl] -1H-1,2,4-triazole (Compound No. 393) O-isopropyl-2- (1-methylpyrrole) carbohydroxymoyl chloride 1.2 g (6.0 mmo)
l) 0.8 g of 1H-1,2,4-triazole (12
mmol) and potassium carbonate 1.7 g (12 mmol)
Was added to 50 ml of N, N-dimethylacetamide to give 13
The mixture was heated and stirred at 0 to 150 ° C for 8 hours. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, the residue was purified by column chromatography, and 1.0 g of the desired product having a refractive index of 1.5519 at 20 ° C. (yield 71 .4%) was obtained.

Production Example 8 1- (O-isopropyl-5-chloro-1-methyl-4)
-Pyrazolecarbohydroxymoyl) -1H-1,
Preparation of 2,4-triazole (Compound No. 651) O-isopropyl-5-chloro-1-methyl-4-pyrazolecarbohydroxymoyl chloride 3.5 g (15
mmol), 1H-1,2,4-triazole 1.1 g
(18 mmol) and 3.1 g of potassium carbonate (23 mm
ol) was added to 50 ml of N, N-dimethylacetamide, and the mixture was heated with stirring at 130 ° C. for 8 hours. The reaction solution was naturally cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer is washed with water, dried over anhydrous magnesium sulfate, the solvent is removed under reduced pressure, the residue is purified by column chromatography, and 1.9 g of the desired product having a melting point of 77.0 to 80.0 ° C.
(Yield 47.5%) was obtained.

Production Example 9 1- [O-isopropyl-5- (1-hexynyl) -2
-Thiophenecarbohydroxymoyl] -1H-1,
Preparation of 2,4-triazole (Compound No. 306) 1- (O-isopropyl-5-bromo-2-thiophenecarbohydroxymoyl) -1H-1,2,4-triazole 1.0 g (3 mmol), 1-hexyne 0.8 g
(10 mmol), bis (triphenylphosphine) palladium (II) chloride 50 mg and cuprous iodide 50
Add 30 mg of triethylamine to 30 ml under reflux and
Stir for hours. The reaction mixture was filtered, the filtrate was concentrated, and the residue was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, the residue was purified by column chromatography, and 0.7 g of the target product having a refractive index of 1.5840 at 20 ° C (yield 77.8%) was obtained. ) Got.

The insecticide of the present invention comprises a carbohydroxymoylazole derivative represented by the general formula [I] as an active ingredient.

In order to use the compound of the present invention as an insecticide, the compound of the present invention may be used by itself, but it may be mixed with a carrier, a surfactant, a dispersant or an auxiliary agent generally used for formulation. It can also be used by formulating into a powder, a wettable powder, an emulsion, a fine granule or a granule. As a carrier used in the formulation, solid carrier such as Sieglite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea, isopropyl alcohol, xylene, cyclohexane, methylnaphthalene, etc. Examples include liquid carriers. Surfactants and dispersants include alkylbenzene sulfonic acid metal salts, dinaphthylmethane disulfonic acid metal salts, alcohol sulfate ester salts, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryls. Examples thereof include ether and polyoxyethylene sorbitan monoalkylate. Examples of the auxiliary agent include carboxymethyl cellulose, polyethylene glycol, gum arabic and the like. Before use, dilute to an appropriate concentration and spray or apply directly.

The insecticide of the present invention can be used by foliage application, soil application, nursery box application, water surface application, or the like. The blending ratio of the active ingredient is appropriately selected as necessary, but in the case of powder or granules, it is 0.05 to 20.
% (Weight), preferably 0.1% to 10% (weight) is appropriately selected. When used as an emulsion or wettable powder, 0.5 to 80% (by weight) is suitable. Preferably 1
It is preferable to appropriately select from the range of 60% (weight).

The application rate of the insecticide of the present invention varies depending on the kind of compound used, target pest, development tendency, degree of damage, environmental conditions, dosage form used, etc. If you do, 10 as the active ingredient
0.05 g to 5 kg per are, preferably 0.1 g to
It is preferable to appropriately select from the range of 1 kg. When it is used in a liquid state such as an emulsion and a wettable powder, it is 0.1 to 5,000.
It may be appropriately selected from the range of 0 ppm, preferably 1 to 1,000 ppm.

The insecticide of the present invention includes other insecticides, fungicides,
Fertilizers and plant growth regulators can also be mixed and used.

Next, the formulation method will be specifically described with reference to typical formulation examples. The types and compounding ratios of the compounds and additives are not limited to these, and can be changed in a wide range. In the following description,% indicates weight percentage.

Formulation Example 1 Emulsion compound (5) 30%, cyclohexanone 20%, polyoxyethylene alkylaryl ether 11%, calcium alkylbenzene sulfonate 4% and methylnaphthalene 35% were uniformly dissolved to obtain an emulsion.

Formulation Example 2 Wettable powder compound (173) 40%, diatomaceous earth 15%, clay 15
%, White carbon 25%, sodium dinaphthylmethanedisulfonate 2% and sodium ligninsulfonate 3% were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 3 2% of powder compound (47), 5% of diatomaceous earth and 93% of clay were uniformly mixed and ground to give a powder.

Formulation Example 4 Granule compound (317) 5%, lauryl alcohol sulfate sodium salt 2%, sodium ligninsulfonate 5%, carboxymethylcellulose 2% and clay 86
% Uniformly mix and grind. 20 parts by weight of water was added to 100 parts by weight of this mixture, and the mixture was kneaded.
After being processed into particles of ˜32 mesh, it was dried to obtain granules.

[0085]

INDUSTRIAL APPLICABILITY The carbohydroxymoylazole derivative of the present invention is used for planthoppers such as brown planthopper, sedge loach, and brown planthopper, leafhoppers such as leafhopper leafhoppers, green leafhoppers, aphids such as cotton aphid, green peach aphid, and radish aphid, whitefly whitefly. And other whiteflies, larvae and other scale insects and stink bugs and other stink bugs, hemiptera pests, diamondback moth, Pleurotus spp., Etc., lepidopteran pests such as Hasmonyototo, etc. It is effective for the control of Coleoptera pests such as Adzuki bean weevils and urchin beetles, and Orthoptera pests such as American cockroaches and German cockroaches. Particularly, it exhibits an extremely excellent control effect on susceptible and resistant planthoppers and pest insects such as leafhoppers, aphids, whiteflies, scale insects and stink bugs.

Next, the effect of the compound of the present invention will be described with reference to test examples. The comparative drug a used was the compound described in the specification of US Pat. No. 4,599,348.
This comparative drug was formulated and used in the same manner as the test compound. Comparative drug a: 1- (O-methyl-t-butylhydroxymoyl) imidazole

Test Example 1 Black leafhopper insecticidal test A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm. Rice foliage was soaked in the drug solution, air-dried, and then allowed to stand in a test tube. Five larvae of the leafhopper leafhoppers were released therein and capped with absorbent cotton. Then, it was placed in a constant temperature room at 25 ° C., and two days later, the number of dead insects was investigated and the mortality rate was calculated. The determined mortality was evaluated according to the criteria in Table 35, and the results are shown in Table 36. In addition, the test was conducted in two consecutive systems.

[0088]

[Table 35]

[0089]

[Table 36]

Test Example 2 Testimony of insecticide for brown planthopper The wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 500 ppm. Rice foliage was soaked in the drug solution, air-dried, and then allowed to stand in a test tube. The brown planthopper larva 1 in it
Zero cows were released and capped with absorbent cotton. After that, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was investigated and the dead insect rate was calculated. The obtained mortality was evaluated according to the criteria of Table 35, and the results are shown in Table 37. In addition, the test was conducted in two consecutive systems.

[0091]

[Table 37]

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI C07D 405/06 C07D 405/06 409/06 409/06 C07F 7/10 C07F 7/10 A (72) Inventor Hiroshi Kurihara Shizuoka Prefecture 4-6, Aobadai, Kikugawa-cho, Ogasa-gun 4 (72) Inventor Tadami Hirano 2-9-3, Katsurugaoka, Kakegawa-shi, Shizuoka (56) Reference JP-A-3-68559 (JP, A) JP-A 1- 308260 (JP, A) (58) Fields investigated (Int.Cl. ⁷ , DB name) C07D 403/06 C07D 249/08 C07D 405/06 C07D 409/06 C07F 7/10 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. A general formula [Chemical 1] (Where A is the formula [Chemical 2] Represents a heterocycle represented by₁~ C₆Alkyl
Base, C₁~ C₆Haloalkyl group, C_Three~ C₆Cycloal
Kill group, C_Two~ C₆Alkenyl group, phenyl group, benzyl
Lu group, C₁~ C₆Acyl group, naphthylcarbonyl group,
Nzoyl group, C₁~ C₆Alkoxycarbonyl group, cal
Vamoyl group, N-C₁~ C₆An alkylcarbamoyl group,
C₁~ C₆Alkylsulfonyl group, phenylsulfonyl
Base, C₁~ C₆Alkoxy C₁~ C₆Alkyl group, C₁
~ C₆Alkylthio C₁~ C₆Alkyl group, francal
Bonyl group, thiophene carbonyl group, pyridyl carbonyl
Group, optionally substituted pyridyl group or pyrimidinyl
Group, R¹Is a hydrogen atom, C₁~ C₆Alkyl group
Represents a phenyl group or a benzyl group, X is a hydrogen atom, C₁
~ C₈Alkyl group, C_Three~ C₆Cycloalkyl group, C_Three
~ C₆Cycloalkyl C ₁~ C₆Alkyl group, C_Three~ C
₆Cycloalkenyl group, C₁~ C₈Haloalkyl group, C
₁~ C₈Alkoxy group, trimethylsilyl group, trimethyl
Lucilil C₁~ C₆Alkyl group, trimethylsilyl C₁
~ C₆Alkoxy group, trimethylsilyl C_Two~ C₆Al
Quinyl group, C_Two~ C₈Alkenyl group, C_Two~ C₈Archi
Nyl group, phenyl group, benzyl group, optionally substituted phenyl group
Noxy group, cyclohexenylidene C₁~ C₆Alkyl
Group, halogen atom or optionally substituted phenylthio
Group, W is a nitrogen atom or a methine group, and n is 1
Indicates an integer of ˜3. ) Carbohydroxymo
Iluazole derivative. 2. An insecticide containing the carbohydroxymoylazole derivative according to claim 1 as an active ingredient.