JPS63270662A - Benzoylurea derivative, its production and insecticidal miticide containing said compound as active component - Google Patents

Abstract

NEW MATERIAL:The benzoylurea derivative of formula I (X1 is H or Cl; X2 is H or F). EXAMPLE:N-2,6-difluorobenzoyl-N-[2-fluoro-4-[2-(3-chloro-5-trifluorome thyl)pyri dyloxy]]phenylurea. USE:An insecticidal and miticidal agent. It has excellent insecticidal activity especially against larva of vermin and high miticidal activity against spider mite. It can be produced at a relatively low cost. PREPARATION:The objective benzoylurea derivative of formula I can be pro duced by reacting a benzoylisocyanate compound of formula II with an aniline compound of formula III.

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 and acaricide 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).
Publication No. 1987-58786, Japanese Patent Publication No. 1987-5878-
89069, JP-A-57-126460, etc.), and some are already commercially available.

<Problems to be solved by the invention> However, these compounds are insufficiently effective or! l! ! However, it is difficult to say that this method is necessarily satisfactory, as it has problems with manufacturing costs.

<Means for Solving the Problems> In view of the above circumstances, the present inventors conducted intensive studies to develop a benzoyl urea compound having superior insecticidal activity, and as a result, the present inventors developed a compound represented by general formula (2). It has been discovered that benzoyl urea derivatives have excellent insecticidal activity, particularly extremely high insecticidal activity against pest larvae, and also have high acaricidal activity against spider mites, and can be produced at relatively low cost, This led to the present invention.

That is, the present invention provides general formula (1) [wherein, Xl represents a hydrogen atom or a chlorine atom, x,
represents a hydrogen atom or a fluorine atom, and t] represents an insecticide or acaricide containing a benzoyl urea derivative (hereinafter referred to as the compound of the present invention) as an active ingredient.

Specific pest insects for which the compounds of the present invention are particularly effective include, for example, Lepidoptera larvae such as the diamondback moth, Japanese mealybug, brown borer moth, and armyworm; Diptera larvae such as Culex mosquito and house fly; Reciptera nymphs such as the German cockroach; and Coleoptera larvae. In addition to insects such as , spider mites such as two-spotted spider mite, false red spider mite, Kanzawa spider mite, citrus spider mite, and apple spider mite, etc.

Next, the manufacturing method will be explained in detail.

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

[Manufacturing method A]

A benzoyl isocyanate compound represented by a monofunctional formula (
4) In formula c, XX and X represent the same meanings as above. ] A method of reacting with an aniline compound represented by

[Manufacturing method B]

A method of reacting a penzamide compound represented by the formula I with an isocyanate compound represented by the general formula 1 [wherein Xl and X2 represent the same meanings as above].

In the above production methods A and B, 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, halogenated hydrocarbons such as chlorobenzene, carbon tetrachloride, chloroform, methylene chloride, and 1,2-dichloroethane, diethyl ether, tetrahydrofuran,
Examples include ethers such as dioxane, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, dimethyl sulfoxide, dimethyl formamide, nitromethane, and mixed solvents thereof.

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, there is no problem even if one of the raw material compounds is used in an excess amount.

In production methods A and B, the reaction temperature is not particularly limited, but in production method A, it is generally 0 to 80
℃, usually in the range of room temperature to 60℃, and in production method B, generally room temperature to 160℃, usually 80 to iao
The range is between ℃.

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

The benzoyl isocyanate compound represented by general formula (9) and the penzamide compound represented by general formula (5) used in this production method are known compounds. Further, the aniline compound represented by the general formula (3) is, for example,
It can be manufactured by a known method described in JP 6-40667 or the like or a method similar thereto.

Further, the isocyanate compounds represented by the general formulas can be easily produced by reacting the aniline compound represented by the general formula (2) with phosgane according to a conventional method.

When the compound of the present invention is used as an active ingredient of an insecticide or acaricide, it may be used as it is without adding any other ingredients, but it is usually a solid carrier, a liquid carrier, a gaseous carrier, or a surfactant. , other formulation auxiliaries, baits, etc., and used in formulations such as emulsions, wettable powders, powders, granules, oils, aerosols, and poison baits.

In these preparations, the content of the compound of the present invention as an active ingredient is 0.01% to 96% by weight.

Examples of solid carriers include fine powders such as kaolin clay, abtapulgite clay, bentonite, acid clay, beef illite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Alternatively, granular materials can be mentioned, and examples of liquid carriers include aliphatic hydrocarbons such as kerosene and kerosene,
Aromatic hydrocarbons such as benzene, toluene, xylene, and methylnaphthalene; halocarbons such as dichloroethane, trichloroethylene, and carbon tetrachloride; alcohols such as ethylene glycol and cellosolve; ketones such as acetone, methyl ethyl ketone, cyclohexanone, and isophorone; and diethyl ether. , ethers such as dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles 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, wet layer, etc. include alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts,
Anionic surfactants such as polyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxybrobylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan Examples include nonionic surfactants such as fatty acid esters. Examples of formulation aids such as fixing agents and dispersants include lignin sulfonate and algin f!
IItX, polyvinyl alcohol, gum arabic, VN
Honey, casein, gelatin, CMC (carboxymethyl cellulose), pine oil, agar, etc. are listed, and as stabilizers, for example, PAP (isopropyl acid phosphate), TC
Alkyl phosphates such as P (phosphoric acid, tricrezyl), vegetable oil, epoxidized moieties, the above-mentioned surfactants, antioxidants such as BIT and BHA, fatty acid salts such as sodium oleate and calcium stearate, oleic acid Examples include aliphatic esters such as methyl 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 conditioners, etc.

When the compound of the present invention is used as an insecticide or acaricide, the application rate is usually 0.5 to 500 f per 10 ares, and when applied after diluting an emulsion or wettable powder with water,
The application concentration is x ppm to 11,000 ppm, and powders, granules, oils, aerosols, etc. are applied as they are without any dilution.

<Examples> Hereinafter, the present invention will be explained in more detail with reference to production examples, formulation examples, and test examples, but the present invention is not limited thereto.

Production Example 2 - Fluoro-4-(2-(8-chloro-5-trifluoromethyl)pyridyloxycoaniline 0.09F was dissolved in 6 mj of toluene, and 2
．． 6-cyfluoropenzoyl isocyanate, -0.05
A solution of F in 4 ml of toluene was added dropwise. After the dropwise addition was completed, the reaction solution was stirred at room temperature overnight, and 6 m of n-hexane was added to it.
The crystals formed by adding J are collected by filtration and dried. )
, N-2,6-cyfluorobenzoyl-N-[2-fluoro-4-C2-CB-chloro-5-trifluoromethyl)pyridyloxy)]phenylurea 0.11 f was obtained as white crystals (compound (1)).

Yield: 77% m, p,: 164.9°C Compounds produced by the same method as above are shown in Table 1.

Examples of formulations are shown below. Parts are parts by weight.

The compounds of the present invention are indicated by compound numbers in Table 1.

Formulation Example 1 10 parts each of the compounds (1) to (8) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 85 parts of xylene and 85 parts of dimethylformamide were thoroughly mixed to form each compound. Obtain emulsion.

Formulation Example 2 20 parts each of the compounds (1) to (8) of the present invention, 10 parts of fenitrothion, 8 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 66 parts of synthetic hydrated silicon oxide.
Thoroughly grind and mix the two parts to obtain each wettable powder.

Formulation Example 8 1 part of each of the compounds (1) to (8) of the present invention, 2 parts of carbaryl, 87 parts of kaolin clay and 1 part of talc are thoroughly ground and mixed to obtain q powders.

Formulation Example 4 5 parts each of the compounds (1) to (8) of the present invention, 1 part of synthetic hydrated silicon oxide, 2 parts of calcium lignin sulfonate, 80 parts of bentonite and 62 parts of kaolin clay were thoroughly ground and mixed, and water was added. After thoroughly kneading, the mixture is granulated and dried to obtain each granule.

Next, a test example is shown. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.

Part 11 Table 2 Test Example 1 Each emulsion of the following invention compound obtained according to Formulation Example 1 was diluted with water to a concentration of 8.5 ppm. 100 mj of the diluted solution was put into a 180 mj polycup, and 20 entangled larvae of A. crucianum 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 3.

Test Example 2 A 20,000-fold dilution with water of each of the emulsions of the following inventive compounds and comparative control compounds obtained according to Formulation Example 1 (
2 mj (equivalent to 0.5 ppm) was impregnated into 18F artificial feed for Spodoptera japonica and placed in a polyethylene cup with a diameter of 11 cIR. There is one 4th instar larva in it.
0 insects were released, and 6 days later, the number of dead insects was investigated and the number of dead insects was determined (2 repetitions).

The results are shown in Table 4.

Table 4 Test Example 8 -
10 adult female spider mites per leaf, 2
It was stored in a constant temperature room at 5°C.

After 6 days, each emulsion of the compound of the present invention and the comparative compound obtained in the same manner as in Formulation Example 11 was mixed with water to a concentration of 50% of the active ingredient.
Dilute to 0 ppm and turn it to 1 on a turntable.
15 mj was sprayed per pot and 2 mj was irrigated into the soil at the same time. After 20 days, the degree of damage caused by spider mites to the 8th true leaves of common beans was investigated.

The degree of damage was divided into the following eight levels.

−; Damage is rarely observed.

+: Slight damage is observed.

++: The same damage as in the untreated area is observed.

The results are shown in Table 5.

<Effects of the Invention> The compound of the present invention can be applied to the diamondback moth, the Japanese dwarf moth, the kobno borer moth,
It is not only effective against various harmful insects such as Iptera larvae such as armyworms, Diptera larvae such as Culex mosquitoes and houseflies, and Ophthalmia nymphs such as the Chinese cockroach, but also particularly effective against the larvae of Naminoptera mites. It is also effective against 71 mites, such as the Japanese red spider mite, the Japanese red spider mite, the Japanese red spider mite, the red spider mite, and the apple spider mite, so it can be used for various purposes.

Claims (4)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X_1 represents a hydrogen atom or a chlorine atom,
_2 represents a hydrogen atom or a fluorine atom. ] A benzoyl urea derivative represented by (2) 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_1 represents a hydrogen atom or a chlorine atom,
_2 represents a hydrogen atom or a fluorine atom. [In the formula, X_1 and X_2 represent the same meanings as above. ] A method for producing a benzoyl urea derivative. (3) 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_1 represents a hydrogen atom or a chlorine atom,
_2 represents a hydrogen atom or a fluorine atom. [In the formula, X_1 and X_2 represent the same meanings as above. ] A method for producing a benzoyl urea derivative. (4) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X_1 represents a hydrogen atom or a chlorine atom,
_2 represents a hydrogen atom or a fluorine atom. ] An insecticide and acaricide characterized by containing a benzoyl urea derivative represented by the following as an active ingredient.