JPS6117569A - Benzimidazole derivative, its preparation and insecticidal and miticidal agent containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The benzimidazole derivative of formula I (R1 is H or alkyl; R2 and R3 are H, halogen, nitro, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, etc.; R2 and R3 may together form a 5-6-membered ring containing 0-2 O or S atoms in the ring; X is O, S, methylene, sulfonyl, sulfinyl or imino). EXAMPLE:2-Methyl-1-[4=(3-tolyloxyl)benzyl]benzimidazole. USE:Insecticidal and miticidal agent. PREPARATION:The objective benzimidazole derivative of formula I can be prepared by reacting the benzimidazole compound of formula II with the substituted benzyl compound of formula III (Y is halogen, tosyloxy or mesyloxy) in the presence of an acid acceptor.

Description

Detailed Description of the Invention The present invention relates to compounds of the general formula CI) [wherein R1 represents a hydrogen atom or a lower alkyl group, R2 and Rg are the same or different, and represent a hydrogen atom, a halogen atom, a nitro group, a cyano group or an optionally substituted lower alkyl group, lower alkenyl group, lower alkynyl group, lower cycloalkyl group, lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower cycloalkoxy group, lower alkylthio group, It represents a lower alkenylthio group, a lower alkynylthio group, a lower cycloalkylthio group, a lower dialkylamino group, a lower alkylsulfonyl group, or a lower alkylsulfinyl group, and by bonding R2 and R8 at the terminal, an oxygen atom or a sulfur atom An optionally substituted, saturated or unsaturated 5- or 6-membered ring containing 0 to 2 of the above can be formed. X is an oxygen atom,
Represents a sulfur atom, methylene group, sulfonyl group, sulfinyl group or imino group. ] The present invention relates to a benzimidazole derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, and an insecticide and acaricide containing the same as an active ingredient.

Certain benzimidazole derivatives, such as 1-(
Agric reports that 8,7-dimethyloct2,6-genyl)benziεdazole has insecticidal efficacy against house flies and the like.

Biol, Chem, 46(6) 1715(
1982). However, these compounds cannot necessarily be said to be sufficient as active ingredients for insecticides.

The compounds of the present invention have excellent insecticidal efficacy against Diptera pests such as Culex Culex and Culex Culex. In addition, it has excellent acaricidal efficacy against spider mites such as false red spider mite and citrus spider mite, and is also highly effective against spider mites that have developed resistance to existing acaricides.
It can be used as an active ingredient in acaricides, epidemic prevention insecticides, etc.

In the compound of the present invention represented by general formula (I), R2 and R8 are described in more detail as follows. That is, R2 and R8 include a hydrogen atom, a halogen atom, a 77L/*lejf5 having 1 to 8 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a fulkynyl group having 2 to 6 carbon atoms, and a fluorine group having 2 to 6 carbon atoms. Synoloalkyl group having 8 to 6 carbon atoms, noalkoxy group having 1 to 6 carbon atoms, alkoxy group having 2 to 6 carbon atoms 71/2 * cy group, carbon atom! Alkynyloxy group having 2 to 6 carbon atoms, cycloalkyloxy group having 8 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, alkenylthio group having 2 to 6 carbon atoms, alkynylthio group having 2 to 6 carbon atoms Group, carbon atom! Cycloalkylthio group having 8 to 6 carbon atoms, dialkylamino group in which each alkyl group has 1 to 6 carbon atoms, alkylsulfonyl group having 1 to 6 carbon atoms, alkylsulfonyl group having 1 to 6 carbon atoms, carbon atom Haloalkyl group having 1 to 6 carbon atoms, haloalkenyl group having 2 to 6 carbon atoms, haloalkynyl group having 2 to 6 carbon atoms, haloalkoxy group having 1 to 6 carbon atoms, haloalkenyl having 2 to 6 carbon atoms Oxy group, haloalkynyloxy group having 2 to 6 carbon atoms, haloalkylthio group having 1 to 6 carbon atoms, haloalkenylthio group having 2 to 6 carbon atoms, haloalkynylthio group having 2 to 6 carbon atoms, Haloalkylsulfonyl group having 1 to 6 carbon atoms, carbon atom B1 to
6 haloalkylsulfinyl group, alkoxyalkyl group having 2 to 6 carbon atoms, 1 haloalkoxyalkyl group having 2 to 6 carbon atoms, alkylthioalkyl group having 2 to 6 carbon atoms, haloalkylthio having 2 to 6 carbon atoms Alkyl group, alkoxyalkoxy group having 2 to 6 carbon atoms, haloalkoxyalkoxy group having 2 to 6 carbon atoms, alkenyloxyalkyl group having 8 to 6 carbon atoms, 8 carbon atoms
~6 alkynyloxyalkyl group, 8 to 6 carbon atoms
alkenyloxydialkoxy group, 3 to 6 carbon atoms
Alkynyloxydialkoxy group, carbon atom -f-92~
6 alkoxyalkylthio group, alkylthioalkylthio group having 2 to 6 carbon atoms, or alkylthioalkoxy group having 2 to 6 carbon atoms, 8.4-methylenedioxy group, 8゜4-difluoromethylenedioxy group, 8.4 Examples include -trifluoroethylenedioxy group, 8.4-)limethylene group, and 3.4-tetramethylene group.

Desirable compounds among the compounds of the present invention represented by general formula (I) are those in which R1 represents a hydrogen atom or a methyl group, and R1 represents a hydrogen atom or a methyl group;
2 and R8 are the same or different, hydrogen atom, halogen atom, number of carbon atoms 1 to 8 (7) 7 JL/ Ki3
1/ group, an alkoxy group having 1 to 6 carbon atoms, or an alkylthio group having 1 to 6 carbon atoms, and X is a compound representing an oxygen atom, a sulfur atom, a methylene group or a sulfonyl group.

The compound of the present invention has the general formula (II) [wherein R1 represents the same meaning as the above-mentioned -]. A benzimidazole compound represented by the general formula (m) [wherein R2, RB and X have the same meanings as above, and Y represents a halogen atom, tosyloxy group or mesyloxy group. ] It can be produced by reacting the substituted benzyl compound shown in the following in the presence of an acid binding agent.

In this method, the acid binder includes, for example, alkali metals such as lithium, sodium, and potassium, alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal amides such as sodium amide, sodium hydroxide, and potassium hydroxide. Examples include alkali metal hydroxides such as, alkali metal carbonates such as sodium carbonate and potassium carbonate, and organic bases such as triethylamine and N,N-diethylaniline.

This reaction can be carried out in the presence or absence of a solvent, but is usually carried out in the presence of a solvent at a temperature ranging from -80°C to the boiling point of the reaction mixture, generally from 0°C to 110°C. . The reaction is generally complete in 0.5 to 50 hours.

Examples of solvents include water, hydrocarbons such as benzene, toluene, and xylene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and dimethoxyethane;
Examples include ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone, acid amides such as dimethyl formamide, diethyl formamide, and dimethyl acetamide, dimethyl sulfoxide, and mixtures thereof.

In addition, in this reaction, a phase transfer catalyst such as benzyltriethylammonium chloride and tetrabutylammonium bromide can also be used.

In this reaction, the molar ratio of the benzimidazole compound represented by the general formula (If) and the substituted benzyl compound represented by the general formula (m) is 1:0.1 to 10,
Usually the ratio is 1:0.8 to 1.0. Moreover, the molar ratio of benzimidazole and acid binder is suitably 1:0.9 to 1.1.

After the reaction is completed, usual post-treatments are carried out, and if necessary, purification is carried out by chromatography, distillation, recrystallization, etc.

The compounds of the present invention also include inorganic acid salts such as hydrochloric acid and sulfuric acid, and organic acid salts such as trifluoroacetic acid of the benzimidazole derivative of general formula (1).

Examples of the benzimidazole compound represented by the general formula (I[) include benzimidazole, 2-methylbenzimidazole, and 2-ethylbenzimidazole.

Further, the substituted benzyl compound represented by the general formula (m) is known or can be easily produced by a method similar to a known method.

Specific examples thereof are shown below, but the invention is not limited to the examples.

That is, 4-phenoxybenzyl bromide, 4-(3
-Tolyloxy)benzyl chloride, 4-(4-n-pentylphenoxy)benzyl chloride, 4-(4-ethoxyphenoxy)benzyl chloride, 4-(8-ethoxyphenoxy)benzyl chloride, 4-(4-methylthiophenoxy)benzyl Chloride, 4-benzoylbenzylbromide, 4-(4-vinyloxyphenoxy)benzyl chloride, 4-(8-chlorophenoxy)benzyl chloride, 4-(2-fluorophenoxy)benzyl p-toluenesulfonate, 4-(8 -fluorophenoxy)benzylbromide, 4-(8-isopropylphenoxy)benzyl chloride, 4-(4,-ethynylphenoxy)benzyl chloride, 4-(8-n-propylthiophenoxy)benzyl chloride, 4-(4- Methanesulfonylphenoxy)benzyl chloride, 4-(8-
trifluoromethylphenoxy)benzyl bromide, 4
-(4-cyclopropylphenoxy)benzyl chloride, 4-(2,chlorophenylthio)benzyl bromide,
4-(8-bromophenoxy)benzylbromide, 4-
(4-ethylphenoxy)benzyl chloride, 4-(8
-ethylphenoxy)benzyl chloride, 4-(8-N
.

N-dimethylaminophenoxy)benzyl bromide, 4
-(8-n-propokylephenoxy)benzyl chloride, 4-(8-n-butoxyphenoxy)benzyl chloride, j-(8-n-pentyloxyphenoxy)benzyl chloride, 4-'(4-isopropy, minor thiol phenoxy)benzyl chloride, 4-(4-(2,2-dichlorovinyl)phenoxyfubenzyl chloride, 4-(8-n
-propylphenoxy)benzyl chloride IJ, 4-(
4-isopropylphenoxy)benzyl chloride, 4-
Benzylbenzyl methanesulfonate, 4-CB-ethylthiophenoxy)benzyl chloride, 4-(4-methoxymethylphenoxy)benzyl chloride, 4-(4
-n-butylthiophenoxy)benzylchlor IJF, 4
-(4-difluoromethoxyphenoxy)benzyl chloride, 4-(4-n-propylphenoxy)benzyl chloride, 4-(4-n-butylphenoxy)benzyl chloride, 4-(8-vinylphenoxy)benzyl chloride, 4- (4-allylphenoxy)benzyl chloride,
4-(4-n-propoxyphenoxy)benzyl chloride, 4-(4-sec-butylphenoxy)benzyl chloride, 4-(2,5-dimethylphenoxy)benzyl chloride, 4-(2,8-dimethylphenoxy)benzyl Chloride, 4-(8,5-difluorophenoxy)7
dDry dibenzyl chloride, 4-(4-n-butoxybenzyl chloride, 4-(4-n-pentylthiophenoxy)benzyl chloride, 4-(8゜4-methylenedioxyphenoxy)benzyl chloride, 4-( 4-allylthiophenoxy)benzyl chloride, 4-(8-allyloxyphenoxy)benzyl chloride, 4-(4-propargyloxyphenoxy)benzyl chloride, 4-(4-n-
hexylphenoxy)benzyl chloride, 4-(4-(
2-butenyl) phenoxyfubenzyl chloride, 4-(
4-(1-methylallyl)phenoxybenzyl chloride, 4-(8-n-hexyloxyphenoxy)benzyl chloride, 4-(8-isopropoxyphenoxy)
Benzyl chloride, 4-(4-(1-methylcycloprobyl)phenoxybenzyl chloride, 4-(8-ethynyloxyphenokyle)benzyl chloride, 4-(4-
Allylthiophenoxy)benzyl chloride, 4-(4-
(2,2-dichlorovinyloxy)phenoxyfubenzyl chloride, 4-(4-(2-chloroallyl)phenoxyfubenzyl chloride, 4-(4-(1,1,2,2-
Tetrafluoroethoxy)phenoxifbenzyl chloride, 4-(8-chloro-4-methylphenoxy)benzyl chloride, 4-(8,4-difluoromethylenedioxyphenoxy)benzyl chloride, 4-(4-56(
-pentylphenoxy)benzyl chloride, 4-(4-
(2-methylallyl)phenoxydibenzyl chloride,
4-(4-(2-chloroethynyl)phenoxydibenzyl chloride, 4-(4-methoxymethylthiophenoxy)benzyl chloride, 4-(4-(2°2.2-trifluoroethoxy)phenoxydibenzyl chloride, 4 −
(4-ethoxymethylphenoxy)benzyl chloride,
4-(8-trifluoromethylthiophenoxy)benzyl chloride, 4-(8-methoxy-4-methylphenoxy)benzyl chloride, 4-(4-propargylphenoxy)benzyl chloride, 4-(4-ethyl-2-methylphenoxy) ) benzyl chloride, 4-(2-methyl-
4-n-propylphenoxy)benzyl chloride, 4-
(4-n-phthyl-2-methylphenoxy)benzyl chloride, 4-(4-(1-methyl-2-butenyl)phenoxy)pensyl chloride, 4-(8-methoxyphenoxy)benzyl chloride, 4-(4- Isopropoxyphenoxy)benzyl chloride, 4 (4-5ec
-butoxyphenoxy)benzyl chloride, 4-(4-
n-pentyloxyphenoxy)benzyl chloride, 4
-(4-(1-ethoxyethyl)phenoxydibenzyl chloride, 4-(8-allylthiophenoxy)benzyl chloride, 4-(4-cyclopropylthiophenoxy)
Benzyl chloride, 4-(8-allyloxymethylphenoxy)benzyl chloride, 4-(4-ethoxyphenylthio)benzyl chloride, 4-(8-ethynyloxymethylphenoxy)benzyl chloride, 4-(4-methylthiomethylthiophenoxy) Benzyl chloride, 4-
(4-isobutylthiophenoxy)benzyl chloride,
4-(4-(2-methylallyloxy)phenoxydibenzyl chloride, 4-(8-ethanesulfonylphenoxy)benzyl chloride, 4-C4-(1゜1-dichloro-2,2-difluoroethoxy)phenoxydibenzyl Chloride, 4-(2-methyl-4-n-propoxyphenoxy)benzyl chloride, 4-(2-chloro-4-ethoxyphenoxy)benzyl chloride, 4-(4-(2
-butenyloxy)phenoxydibenzyl chloride, 4
-C4-(1-methylallyloxy)phenylthio]benzyl chloride, 4-(8-ethoxyanilino)benzyl chloride, 4-(5,6,7,8-tetrahydro-2
-naphthyloxy)benzyl chloride, 4-(4-)o
Mog-ri CI 0 Phenoxy)benzyl chloride, 4-(4-trifluoromethylphenoxy)benzyl chloride, 4-benzenesulfinylbenzylbromide, 4-(8-nitrophenoxy)benzyl chloride, 4-(4-n- Propoxyphenoxy)benzyl chloride, 4-(4-methoxyphenoxy)benzyl chloride, 4-(4-ethylthiophenoxy)benzyl chloride, 4-(4-n-propylthiophenoxy)benzyl chloride, 4-(a-methylthiophenoxy) ) benzyl chloride, 4-(8-n-butylthiophenoxy)benzyl chloride, 4-(4-n-propoxyphenylthio)benzyl chloride, 4-(4-ethylbenzoyl)benzyl chloride, 4-(2,8- dihydrobenzofuran-5-yloxy)benzyl chloride, 4-(2,8-
dihydro-2,2-dimethylbenzofuran-5-yloxy)benzyl chloride, 4-(indan-5-yloxy)benzyl chloride, 4-(4-(2,2,8-trifluoroethoxy)phenoxydibenzyl chloride,
Examples include 4-(4-(2-bromo-1,1,2,2-tetrafluoroethoxy)phenoxy)pencil stop θ.

The following is an example of one-layer construction.

Production Example 1 10 mg of anhydrous dimethylformamide and sodium hydride (62% oil suspension) 0.149 (8,6
0.48F (8.6 mmole) of 2-methylbenzimidazole was added to the mixture with 0.48 mmole (mmole) of 2-methylbenzimidazole.

After stirring at room temperature for 1 hour, it was cooled to 5-10°C and 1.00 f (8,6
mmole ) (D Anhydrous dimethylformamide solution 5- was added dropwise over 80 minutes. After the addition, it was stirred at room temperature overnight. After the reaction was completed, it was poured into 1005 g of water, and 8 g of toluene was added.
Extracted twice at 0d, washed with water, dried over anhydrous sodium sulfate, distilled off the toluene under reduced pressure, and subjected to silica gel column chromatography to obtain 2-methy71/-1- as a colorless liquid (27,0 nD 1.6112). ,(
0.841 of 4-(3-tolyloxy)benzylcobenzimidazole was obtained.

Production Example 2 Toluene 201IIg, 2-methylbenzimidazole o, 55f (4.2mmol), triethylamine 0.429 (4.2mmol) Oyohi, 4-
(4-ethoxyphenoxy)benzyl chloride 1.06
(1 (8.8 mmol) (D) The mixture was stirred under reflux for 5 hours.

After cooling to room temperature, it was washed with water, dried over anhydrous sodium sulfate, toluene was distilled off under reduced pressure, and subjected to silica gel column chromatography to form a colorless liquid (n: 1.5984).
1.20f of 1-(4-(4-ethoxyphenoxy)benzylco-2-methylbenzimidazole) was obtained.

Table 1 shows the compounds of the present invention that can be produced by such a production method.

Table 1 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. It is usually mixed with solid carriers, liquid carriers, gaseous carriers, surfactants, other formulation auxiliaries, baits, etc., or impregnated into base materials such as incense sticks and mats to form emulsions, hydrating powders, etc. Powders, granules, oils,
It is formulated into aerosols, heating fumigants such as mosquito coils and electric mosquito mats, fogging agents such as fogging, non-heating vaporizers, poison baits, etc.

These preparations contain 0.01% to 95% by weight of the compound of the present invention as an active ingredient. Solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, birofuum, and synthetic hydrous silicon oxide. Liquid carriers include kerosene, aliphatic hydrocarbons such as kerosene, and benzene. , toluene, xylene,
Aromatic hydrocarbons such as methylnaphthalene, halogenated hydrocarbons such as dichloroethane, trichloroethylene, carbon tetrachloride, alcohols such as methanol, ethanol, impropatol, ethylene glycol, cellosolve, ketones such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, etc. Ethers such as diethyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate,
Examples include nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, dimethyl sulfoxide, and vegetable oils such as soybean oil and cottonseed oil. Gaseous carriers include chlorofluorocarbon gas, LPG (liquefied petroleum gas), dimethyl ether, and the like. emulsification, dispersion,
Surfactants used for wet carbon include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfonate salts, polyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin, etc. There are anionic surfactants such as condensates, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester.Fixing agents and dispersants. Adjuvants for formulations such as lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, molasses, casein, gelatin, CMC (carboxymethylcellulose), pine oil, agar, etc., and stabilizers include PAP
(acidic isopropyl phosphate), alkyl phosphates such as TCP (tricresyl phosphate), vegetable oils, epoxy Kamiike, the above-mentioned surfactants, antioxidants such as BHT and BHA, fatty acid salts such as sodium oleate and calcium stearate. , methyl oleate, methyl stearate, and other fatty acid esters.

Examples of formulations are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts are parts by weight.

Formulation Example 1 0.2 part of the present compound (1) or (29), 2 parts of xylene, and 97.8 parts of white kerosene are mixed to obtain each oil solution.

Formulation Example 2 The compounds of the present invention are), <29) to (82), C8
6).

(87), (41)-(50), (52),
(54), (55).

10 parts each of (60) to (66), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 70 parts of xylene are thoroughly mixed to obtain each emulsion.

Formulation Example 8 20 parts of the present compound (7) or (66), 10 parts of fenitrothion, 8 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 65 parts of synthetic hydrated silicon oxide.
Thoroughly grind and mix the two parts to obtain each wettable powder.

Formulation Example 4 1 part of the compound (10) or (81) of the present invention, 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 5 5 parts of the compound (15) or (50) of the present invention, 1 part of synthetic hydrous 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 kneading the horse mackerel, the mixture is granulated and dried to obtain each granule.

These preparations are used as they are or diluted with water. In addition, other insecticides, acaricides, nematicides, fungicides,
It can also be used in combination with 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 5 to 500 f per 10 are; when applying an emulsion, wettable powder, etc. diluted with water, the application concentration is 1°ppm - 11,000pp, and powders, granules, oils, aerosols, etc. are applied as a preparation without any dilution.

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.

Table 2 Compound Makoto No. Structural formula Name L: All Test Example 1 An emulsion of the compound of the present invention below obtained according to Formulation Example 2 was diluted with water to a concentration of 3.5 ppm. Diluted liquid 100-
into a 180-poly cup and add 20
The head was released. The survival and death of the animals was investigated on the day after release.

After that, food was added to each plot, and when all of the untreated plots had emerged, the inhibition rate of emergence was investigated.

In addition, the insect mortality rate and the emergence inhibition rate were each divided into the following three stages and displayed.

(Dead rate) A: 90% or more B = less than 90% ~ 1
0% C: less than 10% (inhibition rate of emergence) A: 90% or more B: less than 90% to 80% C2 less than 80% Table 8 Test Example 2 For potted green beans (first leaf stage) 7 days after sowing ,−
10 adult female spider mites per leaf, 2
It was stored in a constant temperature room at 5°C. After 6 days, an emulsion of the compound of the present invention and a control compound below prepared according to Formulation Example 2 was diluted with water so that the active ingredients were 500 ppm, and the emulsion was sprayed on a turntable for 10 m per pot, and at the same time 2- The soil was irrigated.

Eight days later, the degree of damage caused by spider mites to each plant was investigated.

The effectiveness criteria were divided into the following three levels.

In case of -2, there is almost no damage observed.

+: Slight damage is observed.

+: Damage similar to that in the untreated area is observed.

Table 4 Procedural amendment (voluntary) November ls, 1982

Claims (3)

[Claims] (1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. or an optionally substituted lower alkyl group, lower alkenyl group, lower alkynyl group, lower cycloalkyl group, lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower cycloalkoxy group, lower alkylthio group, It represents a lower alkenylthio group, a lower alkynylthio group, a lower cycloalkylthio group, a lower dialkylamino group, a lower alkylsulfonyl group, or a lower alkylsulfinyl group, and by bonding R_2 and R_3 at the terminal, an oxygen atom or a sulfur atom can form an optionally substituted saturated or unsaturated 5- or 6-membered ring containing 0 to 2 of
Represents a sulfur atom, methylene group, sulfonyl group, sulfinyl group or imino group. ] A benzimidazole derivative represented by (2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_1 represents a hydrogen atom or a lower alkyl group. ] Benzimidazole compounds represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. lower alkyl group, lower alkenyl group, lower alkynyl group, lower cycloalkyl group, lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower cycloalkoxy group, lower alkylthio group, lower alkenylthio group, which may be Represents a lower alkynylthio group, lower cycloalkylthio group, lower dialkylamino group, lower alkylsulfonyl group or lower alkylsulfinyl group, and also has 0 to 2 oxygen atoms or sulfur atoms by bonding R_2 and R_3 at the terminals. An optionally substituted saturated or unsaturated 5- or 6-membered ring can be formed within the ring. X represents an oxygen atom, a sulfur atom, a methylene group, a sulfonyl group, a sulfinyl group or an imino group. ] A general formula characterized by reacting a substituted benzyl compound represented by the above in the presence of an acid binder ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R_1, R_2 and R_3 have the same meanings as above. represents. ] A method for producing a benzimidazole derivative represented by (3) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. or an optionally substituted lower alkyl group, lower alkenyl group, lower alkynyl group, lower cycloalkyl group, lower alkoxy group, lower alkenyloxy group, lower alkynyloxy group, lower cycloalkoxy group, lower alkylthio group It represents an alkenylthio group, a lower alkynylthio group, a lower cycloalkylthio group, a lower dialkylamino group, a lower alkylsulfonyl group, or a lower alkylsulfinyl group, and by bonding R_2 and R_3 at the terminal, an oxygen atom or a sulfur atom is removed. ~2 A saturated or unsaturated 5- or 6-membered ring which may be optionally substituted can be formed within the ring. X represents an oxygen atom, a sulfur atom, a methylene group, a sulfonyl group, a sulfinyl group or an imino group. ] An insecticide and acaricide characterized by containing a benzimidazole derivative represented by the following as an active ingredient.