JPS59155344A - Ether compound, its preparation and insecticidal and miticidal agent containing said compound as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R1 is H, F, Cl, Br or methyl; R2 is H or F; R3 is 2-4C alkyl or 2,2,2-trifluoroethyl). EXAMPLE:3-Anilino-4-fluorobenzyl 2,2-dimethyl-2-(4-ethoxyphenyl)ethyl ether. USE:An insecticidal and miticidal agent. Especially effective to Hemiptera such as planthopper, leafhopper, aphid, etc., Lepidoptera such as diamond back moth, cabbage armyworm, etc., Coleoptera such as rice weevil, Japanese beetle, etc., Diptera such as house mosquito, housefly, etc., Orthoptera such as short-winged rice grass hopper, and Dictyoptera such as German cockroach, etc. PREPARATION:The compound of formula I can be prepared by reacting the benzyl halide of formula II (Z is halogen) with an alkali metal salt of the alcohol of formula III.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (r) [wherein R1 is a hydrogen atom]... a nitrogen atom, a chlorine atom,
It represents a bromine atom or a methyl group, R2 represents a hydrogen atom or a hydrogen atom, and R8 represents an alkyl group having 2 to 4 carbon atoms or a 2,2.2-trifluoroethyl group. ] The present invention relates to an ether compound represented by the following, a method for producing the same, and an insecticide and acaricide containing the same as an active ingredient.

As a result of intensive studies to develop excellent insecticidal and acaricidal agents, the present inventors discovered that the ether compound represented by the general formula (I) has high insecticidal and acaricidal effects, The present invention has now been completed.

Specific pest insects for which the compound of the present invention is particularly effective include Hemiptera such as planthoppers, leafhoppers, aphids, and stink bugs; Lepidoptera such as mealybugs and armyworms; Coleoptera such as weevils and bean beetles; Culex pipiens; Examples include Diptera such as the house fly, Orthoptera such as Kobaneipugo, and Orthoptera such as the German cat roach.

The compound of the present invention has the general formula (II) p [wherein R1 and R2 have the same meanings as above, and Z represents a halogen atom. ] Benzyl halide and general formula +111) [In the formula, glaze has the same meaning as above. ] is obtained by reacting the alcohol with an alkali metal salt,
More specifically, for example, the alcohol represented by the general formula It can be produced by reacting benzyl halide represented by Jl) at 0°C to 50°C for 1 to 12 hours.

Examples of the alcohol represented by the general formula On) include the following.

2.2-dimethyl-2-(4-ethoxyphenyl)ethanol2.2-dimethyl-2-(4-n-propyloxyphenyl)ethanol2.2-dimethyl-2(41so-propyloxyphenyl)ethanol2. 2-dimethyl-2-(4-n-butyloxyphenyl)ethanol 2.2-dimethyl-2-(4-(2,2,2-trifluoroethoxy)phenyl)ethanol-1 also has the general formula (II ) Examples of the benzyl halide represented by the formula include the following.

8-Anilinobenzylbromide 8-(4-fluoroanilino)penzyl chloride 8-(4-chloroanilino)benzylbromide 8-(4-bromoanilino)benzylbromide 8-(4-methylanilino)benzylbromide (8 -anilino-4-fluoro)benzylbromide 4-fluoro-8-(4-fluoroanilino)benzyl chloride 4-fluoro-8-(4-chloroanilino)benzyl chloride 4-fluoro-8-(4-bromoanilino)benzyl Bromide 4-Fluoro-8-(4-methylanilino)benzyl bromide Next, an example of the production of the compound of the present invention will be shown.

Production example Synthesis of compound (2) Sodium hydride (60% oil suspension) 11
A solution of 4q (2.86 mmol) and 20 mol of dimethylform 7amide was added dropwise, and the internal temperature was maintained at 5o to 80°C until hydrogen generation was completed.

Thereafter, the mixture was cooled to room temperature, and a solution of 3-anilino-4-fluorobenzyl chloride 61211P (2.60 mmol) in 8 rnL of dimethylformamide was added dropwise, and the mixture was stirred overnight at room temperature. Next, add the reaction mixture solution to 50ml of water.
1, extracted twice with 20ml of ether, dried the ether layer over anhydrous magnesium sulfate, distilled off the ether, and separated by column chromatography packed with silica gel to obtain 83g of 8-Archia. Obtained as a pale orange liquid.

Table 1 summarizes some of the compounds of the present invention that can be produced in the same manner as in the above production examples.

Table 1 OR, pl (Note) Substitution of the ether compound represented by the above general formula, R11, and contents of the auxiliary When the compound of the present invention is used as an active ingredient of an insecticide or acaricide, it is usually prepared using a solid carrier or a liquid. carriers, gaseous carriers or other formulation auxiliaries (e.g. surfactants, dispersants,
Wetting agents, stabilizers, etc.) can be mixed with various preparations such as emulsions, wettable powders, powders, granules, oils, aerosols, heating fumigants (mosquito coils, electric mosquito repellents, etc.), fogging lights, etc. Use as a fog, non-heated fumigant, poison bait, etc.

The active ingredient content in these formulations is between 0.1% and 95%.

Solid carriers include fine powders or powders such as clays (e.g. kaolin, bentonite, acid clay, pyrophyllite, sericite), talcs, and other inorganic minerals (e.g. hydrated silicon dioxide, pumice, diatomaceous earth, sulfur powder, activated carbon). Examples include things like this.

Liquid carriers include alcohols (e.g. methyl alcohol), ketones (e.g. acetone, methyl ethyl ketone), ethers (e.g. ethyl ether, dioxane, cellosolve, tetrahydrofuran), aromatic hydrocarbons (e.g. benzene, toluene, xylene, methyl naphthalene), aliphatic hydrocarbons (e.g. kerosene, kerosene), esters, nitriles, acid amides (e.g. dimethylform 7e, dimethylacedeamide), halogenated hydrocarbons (e.g. dichloroethane, trichloroethylene, carbon tetrachloride) ) etc.

In addition, as surfactants, alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates,
Examples include polyethylene glycol ethers and polyhydric alcohol esters.

In addition, casein, fixing agents and dispersants that can be used include
Gelatin, starch powder, CMC, gum arabic, alginic acid, lignin sulfonate, bentonite, precision,
Examples of stabilizers include polyvinyl alcohol, pine oil, agar, and stabilizers such as PAP (isopropyl phosphate) and 1'
Examples include CP (tricresyl phosphate), tall oil, epoxidized oil, various surfactants, and various fatty acids or esters thereof.

Examples of formulations are shown below.

Formulation Example 1 Dissolve 0.5 part of each of the compounds (1) to (8) of the present invention in white kerosene to make a total of 100 parts to obtain each oil solution.

Formulation Example 2 10 parts each of the compounds (1) to (8) of the present invention, 10 parts of an emulsifier (Tsurpol 8005X (registered trademark of Toho Chemical)), and 70 parts of Kijirol are added to each of them, and these are stirred and mixed well. Obtain the emulsion of

Formulation Example 8 Compound of the present invention (1) 0.2 parts, tetramethrin 0.8
1 part, 5 parts of Kijiroll, and 44.5 parts of deodorized kerosene are mixed and dissolved, filled into an aerosol container, a valve part is attached, and 50 parts of propellant (liquefied petroleum gas) is pressurized and filled through the valve part to form an aerosol. get.

Formulation Example 4 0.2 parts of the compound of the present invention (2), 0.3 parts of the d-trans acid form of allethrin, 8.5 parts of deodorized kerosene, and 1 part of emulsifier (Atmos 300 (registered trademark of Atlask Cal Inc.)) A water-based aerosol is obtained by mixing the mixture with 60 parts of pure water to emulsify it, and then filling it into an aerosol container with 80 parts of a 321 mixture of deodorized butane and deodorized propane.

Formulation Example 5 10 parts of the compound (2) of the present invention and an emulsifier (Sorbo'-
5029-0 (registered trademark of Toho Chemical Co., Ltd.)), add 800 mesh silicon i±85 parts, and stir and mix thoroughly to obtain a wettable powder.

Formulation Example 6 Dissolve 0.5 parts of each of the compounds (1) to (8) of the present invention in an appropriate amount of acetone, add 99.5 parts of 800 Messstarc, stir thoroughly, and then remove the acetone by evaporation. Obtain each powder.

The compounds of the present invention can be widely used as insecticides and acaricides for agricultural and horticultural purposes such as paddy fields, fields, orchards, tea gardens, mulberry gardens, lawns, pastures, forests, etc., and can also be used as insecticides and acaricides for epidemic prevention.

Next, test examples will be given to demonstrate that the compounds of the present invention are useful as active ingredients for insecticides and acaricides.

The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used as comparative controls are indicated by the following compound symbols.

Heating Compound Structural Formula Remarks Test Example 1 R paper of the same size was placed on the bottom of a polyethylene cup with a diameter of 5.5 cm. 7 ml of a 200-fold water dilution (equivalent to 500 ppm) of the emulsion obtained in Formulation Example 2 was dropped onto R paper. 80 sv of sucrose was placed on the paper as bait. Ten female adult house flies were released into the container, the lid was closed, and 48 hours later, their survival and death were investigated to determine the adult rate (2 repetitions).

Test Example 2 2 ml of a 200-fold water dilution (equivalent to 500 PPm) of the emulsion of the compound of the present invention obtained in Formulation Example 2 was impregnated into 1511 artificial feed for armyworm and placed in a polyethylene cup with a diameter of 11 ctn. Ten 8-year-old young and middle-aged Spodoptera were released into the cage, and 24 hours later, they were examined to see if they were alive or dead, and the mortality rate was calculated. (2 repetitions) Test Example 8 A 200-fold water dilution (equivalent to 500 ppm) of an emulsion of 10 female adult spider mites per leaf was applied to 4 leaves of potted green beans 5 days after sowing on a turntable. Ten spider mites were sprayed per pot. Six days later, female adult spider mites on the plants were counted.

The criteria for determining effectiveness is 0 to 9 female adults per 1,000 leaves + 10 to 80.
- It is assumed that 31 or more adult female insects are infested on one leaf. The results are shown below.

141 items displayed in the Showa era
3. Relationship between the person making the amendment and the case Patent applicant address: 5-15-5 Kitahama, Higashi-ku, Osaka, invention of the specification subject to the amendment Detailed explanation column 6, Contents of amendment (]) On page 9, line 8 of the specification, r' 788 J is changed to ['18.8 J and dJ pressure.

(2) Correct the table on page 9 as shown in F.

" ” that's all

Claims (3)

[Claims] (1) General formula (1) [In the formula, R1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or a methyl group, and the auxiliary represents a hydrogen atom or a fluorine atom. Substitute represents an alkyl group having 2 to 4 carbon atoms or a 2.2.2-)lifluoroethyl group. ] An ether compound represented by (2) General formula α1) 'CH2-Z [In the formula, R1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom or a methyl group, and R2 represents a hydrogen atom or]
・Z represents a halogen atom. ] Benzyl halide, denoted by ! : -ff expression O1])
In formula C, Kg is an alkyl group having 2 to 4 carbon atoms, and 2,2
．． Represents a 2-trifluoroethyl group. ] In general formula (I) 1, which is characterized by reacting with an alkali metal salt of an alcohol represented by the above, R1, R2 and R3 have the same meanings as above. ] A method for producing an ether compound shown in the following. (3) General formula (I) R8 In the formula, R1 represents a hydrogen atom, a hydrogen atom, a chlorine atom, a bromine atom, or a methyl group, and R2 represents a hydrogen atom or a hydrogen atom. R8 represents an alkyl group having 2 to 4 carbon atoms or a 2,2,2-trifluoroethyl group. ] An insecticide and acaricide characterized by containing an ether compound as an active ingredient.