JP3101038B2 - Benzohydroxymoylazole derivatives and insecticides - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a benzohydroxymoylazole derivative and an insecticide containing the same as an active ingredient.

[0002]

2. Description of the Related Art The present inventors have already disclosed in Japanese Patent Application Laid-Open No. 1-30882.
In the specification of Japanese Patent Publication No. 60, it was clarified that a benzohydroxymoylazole derivative has an excellent insecticidal activity.

[0003]

However, the insecticidal activity of the compounds specifically described in the specification tends to be still insufficient. In recent years, some of the existing commercially available insecticides generate resistant pests due to long-term use, and some of them have reduced efficacy. In particular, Hemiptera pests such as planthoppers and leafhoppers, aphids, scale insects, whiteflies and stink bugs, cereals such as rice, wheat and potato, fruit trees such as apples and citrus, vegetables such as cucumber, radish and the like. Causes devastating damage to a wide variety of crops and trees. In addition, many Hemiptera pests have shown resistance to existing commercial drugs and have become a problem worldwide. Therefore, it has high efficacy even at low doses,
It is desired to develop an insecticide which is excellent in safety and is useful for resistant pests.

[0004]

Means for Solving the Problems The present inventors have synthesized various benzohydroxymoylazole derivatives and have repeatedly studied their physiological activities. As a result, the compound of the present invention can be used against various pests, especially planthoppers and hemiptera pests such as leafhoppers, aphids, scale insects, whiteflies and stink bugs, as disclosed in JP-A-1-308260.
It has been found that the compound has an extremely excellent insecticidal activity as compared with the compounds specifically described in the specification of Japanese Patent Application Laid-Open No. H10-209,086. In addition, the compound of the present invention has excellent insecticidal activity against harmful insects that are resistant to existing commercial drugs, and has completed the present invention. That is, the present invention provides a compound represented by the general formula [I]:

[0005]

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(Wherein X ₁ represents a hydrogen atom or a halogen atom, X represents a branched alkyl group having 3 or more carbon atoms, a branched alkoxy group having 3 or more carbon atoms, a fluorine-substituted alkyl group having 2 or more carbon atoms, or A halogen-substituted alkoxy group having 3 or more carbon atoms, Y represents an alkyl group, Z represents a nitrogen atom or a methine group), and a insecticide containing the derivative as an active ingredient. It relates to the agent.

[0007] In general formula [I] of the present invention, the halogen atom of X _1, can be mentioned chlorine, bromine, fluorine and iodine atoms. Examples of the branched alkyl group having 3 or more carbon atoms of X include isopropyl, isobutyl, s-butyl, t-butyl, isopentyl, 1-methylbutyl, 2-methylbutyl, neopentyl, isohexyl, 1-methylpentyl, and 2-methylpentyl , 3-
Methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 5-methylhexyl, 3,3-dimethylpentyl, 4,4-dimethylpentyl, 1,3,3-trimethyl Butyl, 2,3,3
-Trimethylbutyl, 3,3-dimethylhexyl, 1,
1,3,3-tetramethylbutyl and the like can be mentioned. Examples of the branched alkoxy group having 3 or more carbon atoms of X include, for example, isopropoxy, isobutoxy, s-butoxy,
t-butoxy, 1-pentyloxy, neopentyloxy, 1-methylbutoxy, 2-methylbutoxy, 1,2
-Dimethylpropoxy, 2-ethylbutoxy, 2,2-
Dimethylbutoxy, 3,3-dimethylbutoxy, 2,
3,3-trimethylpropoxy, 2,2-dimethylpentyloxy, 1,3,3-trimethylbutoxy, 1-ethyl-2,2-dimethylpropoxy, 1-isopropoxy-2-methylpropoxy and the like can be mentioned. . X
As the fluorine-substituted alkyl group having 2 or more carbon atoms,
For example, perfluoroethyl, perfluoropropyl,
Perfluoroisopropyl, perfluorobutyl, perfluoroisopentyl, 4,4,4-trifluoro-
3,3-bis (trifluoromethyl) butyl and the like can be mentioned. Examples of the halogen-substituted alkoxy group having 3 or more carbon atoms of X include, for example, 4,4,4-trifluorobutoxy, 3-chloro-2,2-dimethylpropoxy, 1,1,2,3,3,3 -Hexafluoropropoxy, 2,2-bis (trifluoromethyl) propoxy,
3,3,3-trifluoro-2,2-bis (trifluoromethyl) propoxy, 2,2,3,3,4,4,4-
Heptafluoro-1-methylbutoxy and the like.
As the alkyl group for Y, a linear or branched alkyl group having 1 to 5 carbon atoms, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-
Butyl and t-butyl.

Preferably, in the general formula [I], X ₁
Represents a chlorine atom or a fluorine atom, and X is a branched alkyl group having 3 to 8 carbon atoms, a branched alkoxy group having 3 to 7 carbon atoms, or a part or all of a branched alkoxy group having 3 to 7 carbon atoms is a halogen atom. It is a compound showing a substituted halogen-substituted alkoxy group, Y showing an ethyl group, propyl group, isopropyl group or s-butyl group, and Z showing a nitrogen atom.

The benzohydroxymoylazole derivative represented by the general formula [I] has two stereoisomers, a syn-form and an anti-form, and the present invention relates to these isomers and any of these isomers. Mixtures of ratios are also included. next,
The compounds of the present invention are described in Tables 1A-F. The compound numbers will be referred to in the following description.

[0010]

[Table 1A]

[0011]

[Table 1B]

[0012]

[Table 1C]

[0013]

[Table 1D]

[0014]

[Table 1E]

[0015]

[Table 1F]

The compound of the present invention can be produced by the following methods A to D. Manufacturing method <A>

[0017]

[Reaction formula 1]

(Wherein A represents a halogen atom, X ₁ ,
X, Y and Z have the same meaning as described above. )

That is, the compound of the present invention represented by the general formula [I] is produced by reacting a benzohydroxymoylazole compound represented by the formula [II] with a halogen compound represented by the formula [III] in the presence of a base. can do.
In this reaction, the halogen compound can be used in an equivalent amount or more. Further, as the base that can be used, sodium hydroxide, alkali metal hydroxides such as potassium hydroxide, sodium carbonate, alkali metal carbonates such as potassium carbonate, sodium hydrogen carbonate,
Inorganic bases such as alkali metal bicarbonates such as potassium bicarbonate or triethylamine, N, N-dimethylaniline, pyridine, 1,8-diazabicyclo [5.
4.0] unde-7-cene and the like.

The reaction can be carried out, if necessary, in the presence of a suitable diluent. Examples of the diluent that can be used include water or an inert organic solvent such as ketones such as acetone and butanone, aromatic hydrocarbons which may be halogenated such as benzene, toluene, xylene and chlorobenzene, petroleum ether and ligroin. 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 Is mentioned. The reaction temperature is an arbitrary temperature from 0 ° C. to the reflux temperature in the reaction system, preferably from 40 ° C. to 10 ° C.
0 ° C. The reaction time depends on the compound,
The reaction may be performed for a time. Manufacturing method <B>

[0021]

[Reaction formula 2]

(Wherein B represents a halogen atom, X ₁ ,
X, Y, and Z have the same meaning as described above. )

That is, the compound of the present invention represented by the general formula [I] is reacted with a benzohydroxymoyl halide compound represented by the formula [IV] and an azole or triazole compound represented by the formula [V] in the presence of a base. Can be manufactured. In this reaction, the azole or triazole compound may be used in an equivalent amount or more as well as a base or a solvent. As the base, the same base as that used in Method A can be used.

The reaction can be carried out if necessary in the presence of a suitable diluent. Examples of the diluent that can be used include the same diluents as those used in Method A. The reaction temperature is any temperature from room temperature to the reflux temperature in the reaction system, and is preferably from 80 to 130 ° C. The reaction time varies depending on the compound, but if the reaction is carried out for 2 to 5 hours, the desired product can be produced in good yield. Manufacturing method <C>

[0025]

[Reaction formula 3]

(Wherein, R represents an alkyl group or a halogen-substituted alkyl group, X ₁ represents hydrogen, an alkyl group or a halogen atom, and A ′ represents a halogen atom or an alkyl group.
Sulfonyloxy group, benzenes which may be substituted
Represents a rufonyloxy group, and Y and Z have the same meanings as described above. )

That is, the compound of the present invention represented by the general formula [VIII] comprises a compound having a hydroxyl group on a benzene ring represented by the formula [VI] and a halogen compound or a sulfonic acid ester compound represented by the formula [VII]. It can be produced by reacting in the presence of a base. In this reaction, the halogen compound or the sulfonic acid ester compound can be used in an equivalent amount or more. As the base, A
The same bases as those used in the method can be used.

The reaction can be carried out, if necessary, in the presence of a suitable diluent. Examples of the diluent that can be used include the same diluents as those used in Method A. The reaction temperature is any temperature from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 40 to 120 ° C. The reaction time varies depending on the compound, but the reaction may be carried out for 1 to 8 hours. Manufacturing method <D>

[0029]

[Reaction formula 4]

(In the formula, E represents an alkyl group or a fluorine atom-substituted alkyl group, and X ₁ , Y and Z have the same meanings as described above.)

That is, the compound of the present invention represented by the general formula [X] comprises a compound having a hydroxyl group on a benzene ring represented by the formula [VI] and an alcoholic compound represented by the formula [IX]. It can be produced by reacting in the presence of diethyl dicarboxylate or dimethyl azodicarboxylate. In this reaction, the alcoholic compound can be used in an equivalent amount or more.

The reaction can be carried out, if necessary, in the presence of a suitable diluent. Examples of the diluent that can be used include the same diluents as those used in Method A, and preferably include acetonitrile and tetrahydrofuran. The reaction temperature is any temperature from 0 ° C. to the reflux temperature in the reaction system, and is preferably 30 to
120 ° C. The reaction time varies depending on the compound, but it is 0.1.
The reaction may be performed for 5 to 72 hours.

The general formulas [II], [IV] and [V
The compound represented by I] can be produced by the following methods E, F and G. Manufacturing method <E>

[0034]

[Reaction formula 5]

(Wherein, X ₁ , X, Z, B and n have the same meanings as described above)

That is, the benzohydroxymoylazole compound represented by the general formula [II] can be prepared by converting the benzohydroxymoyl halide compound represented by the formula [XI] in a solvent such as acetonitrile in the presence of a base such as potassium carbonate. In the above, the compound can be produced by reacting with an azole or triazole compound represented by the formula [V]. The reaction temperature is any temperature from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 50 to 80 ° C. The reaction time is
The reaction may be performed for 1 to 6 hours, depending on the compound. Manufacturing method <F>

[0037]

[Reaction formula 6]

(Wherein, X ₁ , X, Y, B and n have the same meanings as described above)

That is, the benzohydroxymoyl halide compound represented by the general formula [IV] can be obtained by converting a benzamide compound represented by the formula [XII] to an aromatic hydrocarbon such as benzene or toluene, or a halogen such as chloroform or carbon tetrachloride. Reaction with a halogenating reagent such as phosphorus pentachloride or thionyl chloride in the presence or absence of an inert solvent such as fluorinated hydrocarbons, or nitriles such as acetonitrile and propionitrile, or aromatic compounds such as benzene and chlorobenzene. It can be produced by reacting with a halogenating agent consisting of triphenylphosphine and carbon tetrachloride or triphenylphosphine and carbon tetrabromide in the presence of an inert solvent such as an aromatic hydrocarbon. In this case, carbon tetrachloride and carbon tetrabromide can be used in combination as a solvent. The reaction temperature is any temperature from 0 ° C. to the reflux temperature in the reaction system, and is preferably from 50 to 80 ° C. The reaction time is
The reaction may be performed for 1 to 6 hours, depending on the compound. Manufacturing method <G>

[0040]

[Reaction formula 7]

(Wherein, X ₁ , Y, Z and m have the same meaning as described above)

That is, the compound represented by the general formula [VI] is prepared by converting the corresponding benzyloxy compound [XIII] into an inert solvent such as water, acetic acid, alcohols, acetates, N, N-dimethylacetamide, N, N-aprotic polar solvents such as dimethylformamide, or palladium-carbon to hydrogenolysis as a catalyst, corresponding benzyloxy compound [XIII], benzene, aromatic hydrocarbons or dichloromethane chlorobenzene,
It can be produced by reacting with boron tribromide or boron trichloride in an inert solvent such as halogenated hydrocarbons such as 1,2-dichloroethane and debenzylating. The reaction temperature is from -60C to 40C, preferably from -30C to room temperature. The reaction time is
The reaction may be performed for 1 to 8 hours, depending on the compound.

The compound represented by the general formula [XI] is prepared by reacting a corresponding benzaldehyde compound with hydroxyamine hydrochloride by a known method to give a corresponding benzaldoxime, which is then reacted with N-bromosuccinimide and N-chlorosuccinic acid. It can be produced by reacting an imide and a halogenating agent such as chlorine. The compound represented by the general formula [XII] can be produced by converting a benzoic acid derivative into benzoic acid halide or imidazole benzoate by a known method, and reacting the compound with an alkoxyamine. In addition, the benzyloxy compound represented by the general formula [XIII] is obtained by benzylating a hydroxybenzoic acid derivative, converting it into a benzoic acid halide by a known method, reacting the benzoic acid halide with an alkoxyamine, and then halogenating the compound according to Method E. After the conversion, it can be produced according to Method B.

[0044]

EXAMPLES Next, the method for producing the compound of the present invention will be described with reference to Examples.
The formulation method and use will be specifically described. Example 1 1- [O-isopropyl-3- (3,3-dimethylbutoxy) benzohydroxymoyl] -1H-1,2,4-
Preparation of triazole (compound 19) 1- [3- (3,3-dimethylbutoxy) benzohydroxymoyl] -1H-1,2,4-triazole 1.6 g
(5.6 mmol) in N, N-dimethylformamide 100 m
Then, 0.16 g (6.7 mmol) of sodium hydride was added, and the mixture was heated and stirred at 80 ° C. for 20 minutes. Naturally cooled to about 50 ° C and further 1.1 g of 2-iodopropane (6.5 mmo
l) was added and reacted at the same temperature for 1 hour to complete the reaction.
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 the refractive index at 20 ° C. was 1.5.
Thus, 1.4 g (yield: 78%) of the target compound of 289 was obtained.

Example 2 Preparation of 1- (O-isopropyl-3-isopentylbenzohydroxymoyl) -1H-1,2,4-triazole (compound 9) O-isopropyl-3-isopentylbenzohydroxymoyl chloride 1 1.5 g (5.6 mmol), 0.8 g (11.6 mmol) of 1,2,4-triazole and 1.6 g (11.6 mmol) of potassium carbonate were added to 100 ml of N, N-dimethylacetamide, and the solution was added at 120 ° C. for 3 hours. The reaction was completed by heating and stirring for an hour. 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, and the residue was purified by column chromatography to obtain 1.4 g of the target compound having a refractive index of 1.5317 at 20 ° C (yield: 82). %)
I got

Example 3 Preparation of 1- (O-isopropyl-3-isobutoxybenzohydroxymoyl) -1H-1,2,4-triazole (Compound No. 3) 1- (O-isopropyl-3-hydroxybenzohydroxy) (Moyl) -1H-1,2,4-triazole 1.2 g
(4.9 mmol), 0.7 g (5.1 mm) of isobutyl bromide
ol) and 0.8 g (5.8 mmol) of potassium carbonate in N, N-
The mixture was added to 100 ml of dimethylformamide, and the reaction was completed at 80 ° C. for 1 hour with stirring. The reaction solution was cooled naturally, poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 1.1 g (yield 73%) of a target substance having a refractive index of 1.5341 at 20 ° C. .

Example 4 Preparation of 1- (O-isopropyl-3-neopentyloxybenzohydroxymoyl) -1H-1,2,4-triazole (compound 44) 1- (O-isopropyl-3-hydroxybenzohydroxy Moyl) -1H-1,2,4-triazole 2.5 g
(10.0 mmol), 0.9 g (10.0 mmol) of 2,2-dimethyl-1-propanol and 2.6 g (10.0 mmol) of triphenylphosphine are dissolved in 40 ml of THF and cooled to below 10 ° C. in a water bath. 1.7 g (10.0 mmol) of diethyl azodicarboxylate is slowly added dropwise to this solution within a temperature range in which the internal temperature does not exceed 20 ° C. After the dropwise addition, the reaction solution is stirred for 24 hours, and then heated to 60 ° C. The reaction solution was concentrated, and the residue was purified by column chromatography to obtain 0.8 g of the target compound having a refractive index of 1.5202 at 20 ° C.
(Yield 25%) was obtained.

Example 5 Preparation of 1- [3- (3,3-dimethylbutoxy) benzohydroxymoyl] -1H-1,2,4-triazole 3- (3,3-dimethylbutoxy) benzohydroxymoyl chloride 2.3 g (9.1 mmol), 1.9 g (27.5 mmol) of 1,2,4-triazole and 1.
5 g (10.9 mmol) of 1,2-dimethoxyethane 100
Then, the mixture was reacted at about 50 ° C. for 8 hours. After natural cooling, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 1.2 g of the desired product (yield: 46%).

Example 6 Preparation of O-isopropyl-3-isopentylbenzohydroxymoyl chloride 5.4 g (23.5 mmol) of O-isopropyl-3-isopentylbenzohydroxamic acid and 9.9 g of triphenylphosphine (37. 8 mmol) and 11.6 g of carbon tetrachloride (7
(5.3 mmol) was added to 200 ml of acetonitrile, and the mixture was heated under reflux for 1 hour. After natural cooling, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 5.1 g of the desired product.
(88% yield).

Example 7 Preparation of 1- (O-isopropyl-3-hydroxybenzohydroxymoyl) -1H-1,2,4-triazole 1- (O-isopropyl-3-benzyloxybenzohydroxymoyl) -1H 5.0 g of -1,2,4-triazole (mp 62-67 ° C.) and 1 g of 10% Pd—C were added to 150 ml of ethyl acetate and subjected to hydrogenolysis at room temperature.
After 8 hours, Pd-C was separated by filtration. The filtrate is concentrated under reduced pressure,
The residue was purified by column chromatography, and 3.2 g of the desired white solid (mp 160-163 ° C) (yield 89)
%).

The insecticide of the present invention comprises a benzohydroxymoylazole derivative represented by the general formula [I] as an active ingredient. To use the compound of the present invention as an insecticide, the compound of the present invention may be used as it is, but a carrier, a surfactant, a dispersant or an auxiliary agent generally used for formulation, and a powder, It can also be formulated and used in wettable powders, emulsions, fine granules or granules. Carriers used in the formulation include zigrite, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon,
Examples include solid carriers such as vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexane, and methylnaphthalene.
Surfactants and dispersants include alkyl benzene sulfonic acid metal salts, dinaphthyl methane disulfonic acid metal salts,
Alcohol sulfates, alkylaryl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monoalkylates and the like. Examples of the auxiliary include carboxymethylcellulose, polyethylene glycol, gum arabic and the like. When used, they are diluted to an appropriate concentration and sprayed or applied directly.

The insecticide of the present invention can be used by foliage application, soil application, nursery box application or water surface application. The blending ratio of the active ingredient is appropriately selected as necessary, but when the powder or granule is used, 0.05 to 20
% (Weight), preferably in the range of 0.1% to 10% (weight). When it is used as an emulsion or a wettable powder, 0.5 to 80% (weight) is appropriate. Preferably 1
It is preferable to appropriately select from the range of ８０80% (weight). The application rate of the insecticide of the present invention varies depending on the type of the compound used, the target pest, the tendency of occurrence, the degree of damage, the environmental conditions, the dosage form used, and the like. 0.05g as active ingredient per 10 ares
-5 kg, preferably 0.1 g-1 kg. When used in the form of a liquid such as an emulsion and a wettable powder, it may be suitably selected from the range of 0.1 to 5,000 ppm, preferably 1 to 1,000 ppm.

The insecticide of the present invention can be used by mixing other insecticides and fungicides. Next, the preparation method will be specifically described with reference to typical preparation 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 30% of compound (9), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene were uniformly dissolved to form an emulsion.

Formulation Example 2 wettable powder 40% of compound (19), 15% of diatomaceous earth, 15% of clay,
25% white carbon, 2% sodium dinaphthylmethanedisulfonate and 3% sodium ligninsulfonate
% Was uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 3 Dust 2% of compound (26), 5% of diatomaceous earth and 93% of clay were uniformly mixed and pulverized to give a dust.

Formulation Example 4 Granules Compound (3) 5%, lauryl alcohol sulfate sodium salt 2%, lignin sulfonate sodium 5
%, Carboxymethylcellulose 2% and clay 86%
Is uniformly mixed and pulverized. 100 parts by weight of this mixture is mixed with water 2
0 parts by weight, kneaded, and extruded using an extrusion granulator.
After processing into a 32 mesh granule, it was dried to obtain a granule.

Formulation Example 5 Dust 6% of compound (46), β-cyclodextrin 12
% And 82% of water in a ball mill for 60 minutes, followed by air drying. 8% of air-dried product obtained, PAP (mixture of diisopropyl phosphate and monopropyl phosphate)
0.3%, 0.3% of soybean crude oil, 0.4% of Carplex # 80 (white carbon manufactured by Shionogi & Co., Ltd.) and 91% of clay were uniformly mixed and pulverized to obtain a powder.

Formulation Example 6 Dust 1.6% of compound (79), 3.2% of activated carbon, 0.3% of PAP (mixture of diisopropyl phosphate and monopropyl phosphate), 0.3% of soybean crude oil, Carplex #
80 1.8% and calcium carbonate 92.8% were uniformly mixed and pulverized to obtain a powder.

[0060]

EFFECTS OF THE INVENTION The compounds of the present invention represented by the general formula [I] can be obtained from the compounds described in Japanese Patent Application Laid-Open No. 1-308260, such as planthoppers such as brown planthopper, brown planthopper and brown planthopper, black leafhopper and green leafhopper. Aphid pests such as leafhoppers, cotton aphids, peach aphids, radish aphids, whitefly such as whiteflies, whitefly such as whiteflies, and insects such as stink bugs such as spiderbugs such as spiders Has improved. In addition, it is also effective in controlling lepidoptera such as diamondback moths, common cutworm, houseflies, dipterans such as house mosquitoes, rice weevil, adzuki beetles, turtle beetles, etc., straight-winged pests such as German cockroaches, and spider mites such as spider mites and orange mites. It is. Furthermore, the compound of the present invention also has a bactericidal activity, and effectively inhibits rice blast, rice sheath blight, cucumber downy mildew, cucumber gray mold, cucumber powdery mildew, cucumber spot bacterial disease, and komatsuna black spot. Can be controlled.

Next, the effects of the compound of the present invention will be described with reference to Test Examples. Test Example 1 Blacktip leafhopper insecticidal test showing resistance to existing drugs (organophosphorus and carbamate insecticides) The wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 20 ppm, and rice stems and leaves were added to the solution. Dipped. After being air-dried, the tube is allowed to stand in a test tube, and contains therein a leafhopper leafhopper larva 10 resistant to existing drugs (organophosphorus and carbamate insecticides).
The head was released and plugged with absorbent cotton. Then, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was examined, and the mortality was calculated and shown in Tables 2A and 2B. The test was performed in duplicate, and as comparative drugs, compounds of the following Chemical Formulas 3 to 8 described in JP-A-1-308260 and BPMC, an existing commercial drug, were used.
(Carbamate insecticide) emulsion and malathion (organophosphorus insecticide) emulsion were used. For existing commercial drugs, tests were performed at a concentration of 1000 ppm.

[0062]

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[0063]

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[0064]

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[0065]

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[0066]

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[0067]

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[0068]

[Table 2A]

[0069]

[Table 2B]

Test Example 2 Insecticidal Test of Brown Planthopper Ingredients A wettable powder prepared according to Formulation Example 2 was diluted with water so as to have a predetermined concentration, and rice stems and leaves were immersed in the chemical solution. After air-drying, the tube was allowed to stand in a test tube, and 10 larvae of brown planthoppers were released into the tube and plugged with absorbent cotton. Then, it was placed in a constant temperature room at 25 ° C., and after 6 days, the number of dead insects was investigated, and the mortality was calculated.
To C. The same compound as in Test Example 1 was used as a comparative drug.

[0071]

[Table 3A]

[0072]

[Table 3B]

[0073]

[Table 3C]

Test Example 3 Cotton Aphid Insecticide Test A wettable powder prepared according to Formulation Example 2 was diluted with water to a concentration of 100 ppm. Cucumber seedlings were immersed in the solution, air-dried, and then placed in a 55 mm diameter polyethylene cup. Ten cotton aphid larvae were released on the leaves. Then 25 ° C
And the number of dead insects was examined three days later, and the mortality was calculated. The test was performed in duplicate and the results are shown in Tables 4A-B.

[0075]

[Table 4A]

[0076]

[Table 4B]

[0077]

────────────────────────────────────────────────── ─── Continued on the front page Examiner Megumi Saito (56) References JP-A-1-308260 (JP, A) JP-A-3-68559 (JP, A) (58) Fields investigated (Int. Cl. ⁷⁾ , DB name) C07D 233/00-233/61 C07D 249/00-249/08 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. A compound of the general formula (Wherein X ₁ represents a hydrogen atom or a halogen atom;
Represents a branched alkyl group having 3 or more carbon atoms, a branched alkoxy group having 3 or more carbon atoms, a fluorine-substituted alkyl group having 2 or more carbon atoms, or a halogen-substituted alkoxy group having 3 or more carbon atoms, Y represents an alkyl group, Z represents a nitrogen atom or a methine group. A benzohydroxymoylazole derivative represented by the formula: 2. An insecticide comprising the benzohydroxymoylazole derivative according to claim 1 as an active ingredient.