JPS63270656A - Benzoylurea derivative, production thereof and insecticide containing said derivative as active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (X is F or H). EXAMPLE:N-2,4,6-Trifluorobenzoyl-N'-(2,5-difluoro-4-trifluoromethoxyph enyl)urea. USE:An insecticide exhibiting excellent insecticidal effect to insect pests such as larve of Lepidoptera, e.g. diamondback moth, rice stem borer or calbage armyworms, larve of Diptera, e.g. common gnat or housefly, young insect of Dictyoptera, e.g. German cockroach, especially larve thereof and producible at a relatively low cost. PREPARATION:A benzoylisocyanate compound expressed by formula II is reacted with an aniline compound expressed by formula III in a solvent such as toluene at room temperature - 60 deg.C to provide the aimed compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel benzoyl urea derivative, a method for producing the same, and an insecticide containing the same as an active ingredient.

<Prior art> It has been known that certain benzoyl urea compounds have insecticidal activity (Japanese Patent Publication No. 52-18255).
JP-A-52-89646, JP-A-57-
126460), and some are already commercially available.

<Problems to be Solved by the Invention> However, these compounds are not necessarily satisfactory, as they are insufficiently effective and have problems in terms of production cost.

<Means for Solving the Problems> In view of the above circumstances, the present inventors conducted extensive studies to develop a benzoyl urea compound having superior insecticidal activity, and as a result, the following general formula (I) was developed. The inventors have discovered that the shown benzoyl urea derivative has excellent insecticidal efficacy, particularly extremely high insecticidal activity against pest larvae, and can be produced at a relatively low cost, leading to the present invention.

That is, in the present invention, in the general formula (I) 1, X represents a fluorine atom or a hydrogen atom. ] The present invention provides a benzoyl urea derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, and an insecticide containing the same as an active ingredient.

Specific pest insects for which the compounds of the present invention are particularly effective include, for example, V4+1 giant larvae such as the diamondback moth, Japanese borer moth, brown borer moth, and armyworms; Diplotera larvae such as Culex mosquito and house fly; Reciptera nymphs such as the German cockroach; and Coleoptera nymphs such as the German cockroach. Examples include larvae.

The compound of the present invention represented by general formula (1) can be produced by the following method.

(Production method A) A benzoyl isocyanate compound represented by the formula (II) and the general formula (
2) In formula 1, X represents the same meaning as above. ] A method of reacting with the aniline compound shown in

(Production method B) A method of reacting a penzamide compound represented by the formula (1) with an isocyanate compound represented by the general formula (■) λ 1, in which X has the same meaning as above.

In the above production methods A and B1, the reaction is usually carried out in the presence of an inert solvent. Examples of solvents that can be used include aromatic hydrocarbons such as benzene, toluene, and xylene, chlorobenzene, carbon tetrachloride, chloroform,
Halogenated hydrocarbons such as methylene chloride, l,2-dichloroethane, ethers such as diethyl ether, tetrahydrofuran, dioxane, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethyl sulfoxide, dimethyl formamide, nitromethane, etc. Examples include mixed solvents.

In production methods A and B, the reaction can generally be carried out under normal pressure, and the objective can usually be achieved in 1 to 60 hours. Further, although the amounts of the raw material compounds used may generally be equimolar ratios, it is also possible to use an excess amount of one of the raw material compounds.

In production methods A and B, the reaction temperature is not particularly limited, but in production method A, it is generally 0 to 80
"01 Usually in the range of room temperature to 60"C, and in production method B, generally room temperature to 160"01 Usually in the range of 80 to 60"C
The range is between 180"C.

The metal product of the present invention thus obtained can be purified by means such as column chromatography, recrystallization, etc., if necessary.

In addition, in this manufacturing method, the aniline compound represented by the general formula @) can be prepared using a known method (Tetra he
drone Lett,, 225B (197B);
2,5-difluorophenol and m
-Fluorophenol or 2,6-diph Atolor4
It can be produced from -ditrophenol, 8-fluoro-4-ditrophenol, and the like. Further, the aniline compound can be converted into an isocyanate compound by reacting it with phosgene according to a conventional method.

When using the compound of the present invention as an active ingredient of an insecticide,
You can use it as is without adding any other ingredients, but
It is usually mixed with solid carriers, liquid carriers, gaseous carriers, surfactants, other formulation auxiliaries, baits, etc., and formulated into emulsions, wettable powders, powders, granules, oils, aerosols, poison baits, etc. used.

In these preparations, the content of the compound of the present invention as an active ingredient is 0.01% to 96% in terms of ff1ffi ratio.

Examples of solid carriers include fine powders or granules such as kaolin clay, attabulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Examples of liquid carriers include aliphatic hydrocarbons such as kerosene and kerosene;
Aromatic hydrocarbons such as benzene, toluene, xylene and methylnaphthalene, halogenated hydrocarbons such as dichloroethane, trichloroethylene and carbon tetrachloride, alcohols such as ethylene glycol and cellosolve, ketones such as acetone, methyl ethyl ketone, cyclohexanone and isophorone, diethyl ether , ethers such as dioxane and tetrahydrofuran, esters such as ethyl acetate, nitrites such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, dimethyl sulfoxide, vegetable oils such as soybean oil and cottonseed oil, and the like. Examples of gaseous carriers include chlorofluorocarbon gas and LPG.
(liquefied petroleum gas), dimethyl ether, etc.

Examples of surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates,
Anionic surfactants such as polyoxyethylene alkylaryl ether ester phosphate salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxybrobylene block copolymers, sorbitan fat/fatty acid esters, polyoxy Examples include non-ionic and onic surfactants such as ethylene sorbitan fatty acid ester. (2) Formulation auxiliaries such as adhesives and dispersants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, molasses, casein, gelatin, MC (kachpoxymethyl cellulose), pine oil, etc. , agar, etc., and examples of stabilizers include PAP (isopropyl acid phosphate),
T(,: Alkyl phosphate such as P (tricresyl phosphate), vegetable oil, epoxidized moiety, the above-mentioned surfactant, B)i
T, B) Antioxidants such as LA, sodium oleishate,
Examples include fatty acid salts such as calcium stearate, and aliphatic esters such as methyl oleate and methyl stearate.

The preparation thus obtained can be used as is or diluted with water. It can also be used in combination with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, fertilizers, soil damage improvers, and the like.

When the compound of the present invention is used as an insecticide, the amount of air to be applied is usually 0.5y to boofI per 10 ares, and when applying an emulsion, wettable powder, etc. diluted with water,
Its application concentration is lIJI)Ill ~ 1000 ppm
Powders, granules, MiJ, aerosols, etc. are applied as they are without any dilution.

Examples> The compounds of the present invention will be explained in more detail below using production examples, formulation examples, and test examples, but the present invention is not limited thereto.

Production Example 1 In a reaction vessel, 0.26 g of 2,6-difluoro-4-trifluoromethoxyaniline was dissolved in 1helene 5-, and 2,4,6-difluorobenzoyl isocyanate was added to this while stirring under water cooling. 0.24F toluene 8W
A solution dissolved in lt was added dropwise. After the dropwise addition was completed, the reaction solution was stirred at room temperature overnight, and n-hexane 6- was added to the resulting crystals, which were separated from P and dried to give N-2,4,6-
Dolifluorobenzoyl-N'-(2,5-difluoro-4-trifluoromethoxyphenyl) urine X0.88F
was obtained as white crystals (compound (l)).

Yield: 66% m, p, : 168-l 69-0 Production Example 2 2.4.6-Dorifluorobenzamide 0,2 Of,
0.25 l of 2-fluoro-4-trifluoromethoxyphenyl isocyanate and 20 m/ml of xylene were charged into a reaction vessel and stirred under reflux for 24 hours. The reaction solution was then cooled and concentrated to obtain a crude product. This crude product was subjected to silica gel chromatography to obtain 0.821 of N-2,4,6-drifluorobenzoyl-N'-(2-fluoro-4-trifluoromethoxyphenyl)urea as white crystals ( Compound (2)).

Yield near 1% m, p: 151.8G Next, a formulation example is shown. The part is N. The compounds of the present invention are indicated by compound numbers in the production examples.

Formulation Example 1 10 parts of compound (1) or (2), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 85 parts of xylene and 85 parts of dimethylformamide are thoroughly mixed to obtain each emulsion.

Formulation Example 2 20 parts of compound (1) or (2), 1 part of fenitrothion
0 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 65 parts of synthetic hydrated silicon oxide are thoroughly ground and mixed to obtain each wettable powder.

Formulation Example 8 1 part of compound (1) or (2), 2 parts of carbaryl, 87 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain each powder.

Formulation Example 4 5 parts of compound (1) or (2), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 8 parts of bentonite
0 part and 62 parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, and then granulated and dried to obtain each granule.

The following test example is shown below. The compounds used for comparison are indicated by compound symbols in Table 1.

Table 1 Test Example 1 Emulsions of the following compounds of the present invention obtained according to Formulation Example 1 were diluted with water to a concentration of 8.5 ppm. A 100-ml diluted solution was placed in a 180-ml polycup, and 20 final instar larvae of the 7-strength Culex mosquito were released. The animals were fed and reared until emergence, and the inhibition rate of emergence was investigated (2 repetitions).

The results are shown in Table 2.

Table 2 Test Example 2 C? According to Formulation Example 1 A 1:10,000 diluted solution (equivalent to 0.5 ppm) of the emulsion of each of the following compounds of the present invention and comparative control compounds with water (2W4t) was soaked into an 18f artificial feed for Spodoptera japonica, and a diameter of 1lcr! I put it in a M polyethylene cup. Ten fourth-instar Spodoptera larvae were released into the larvae, and after 6 days, the survival rate was determined by examining whether they were alive or dead (2 repetitions).

The results are shown in Table 3.

Table 8 Test Example 3 67000-fold dilution H with water of each emulsion of the following inventive compound and comparative control compound obtained according to Formulation Example 1
(equivalent to 1.5 ppm) 1- in a polyethylene cup with a diameter of 5.50 mm
I let it soak inside. Among them, 1 10-day-old nymph
0 animals were released, and 8 days later, the mortality rate was calculated by examining whether they were alive or dead (2
repetition).

The results are shown in Table 4.

Table 4 <Effects of the Invention> The compounds of the present invention can be used to control diamondback moths, Japanese corn borer moths, kobno borer moths,
Since it is highly effective against various pests, such as Lepidoptera larvae such as armyworms, Diptera larvae such as Culex mosquito and house fly, and Reticulata nymphs such as the German cockroach, it can be used for various purposes.

Claims (4)

[Claims] (1) General formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X represents a fluorine atom or a hydrogen atom. ] A benzoyl urea derivative represented by (2) A benzoyl isocyanate compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X represents a fluorine atom or a hydrogen atom. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the aniline compound represented by ▼ [In the formula, X represents a fluorine atom or a hydrogen atom. ] A method for producing a benzoyl urea derivative. (3) A benzamide compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X represents a fluorine atom or a hydrogen atom. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the isocyanate compound represented by ▼ [In the formula, X represents a fluorine atom or a hydrogen atom. ] A method for producing a benzoyl urea derivative. (4) General formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X represents a fluorine atom or a hydrogen atom. ]