JPH03223257A - Pyrazoleoxime derivative and insecticide, acaricide and germicide - Google Patents

Abstract

NEW MATERIAL:A pyrazole oxime derivative expressed by formula I (R1 is H, halogen or 1-5C alkyl; R2 is H or 1-5C alkyl; R3 is 1-8C alkyl, 3-5C alkenyl, 3-5C alkynyl or aralkyl which may be substituted; R4 is H or 1-5C alkyl; (n) is 1-3; A is 1-5C alkylene; X is O or S). EXAMPLE:[1,3-Dimethyl-5-phenoxypyrazole-4-formaldoxime 0-2-[4-(2- methoxyethyl)phenoxy]ethyl ether. USE:Useful as an insecticide, acaricide and germicide. PREPARATION:A compound expressed by formula II is subjected to a reaction with a compound expressed by formula III (Y is eliminable group) in a solvent in the presence of a base or a compound expressed by formula II and a compound expressed by formula III are heated and dissolved to provide the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel pyrazole oxime derivative and an insecticidal, acaricidal, and bactericidal agent containing the same as an active ingredient.

[Conventional technology]

As pyrazole oxime derivatives, for example, JP-A-6
3-183564, the following formula [wherein Rs represents an alkyl group; R6 represents a hydrogen atom or an alkyl group; R7 represents a hydrogen atom; Rs represents an alkylene group; a hydrogen atom, a halogen atom, A group represented by an alkyl group or an alkyl group (wherein R11 and RI3 are the same or different and represent an alkyl group, or R11 and R+3 together represent an alkylene group; R+t represents an alkyl group; B is Represents an oxygen atom or a sulfur atom.

); n represents an integer from 1 to 5; when n represents an integer from 2 to 5, Z may be the same or different]; iR+o represents a hydrogen atom, an alkyl group, or a halogen atom; represent. ] Although it has been disclosed that the compounds represented by the following have insecticidal, acaricidal, and bactericidal activities, it is difficult to say that these compounds have sufficient efficacy.

[Problem that the invention seeks to solve]

An object of the present invention is to provide a novel pyrazole oxime derivative and an insecticidal, acaricidal, and bactericidal agent containing the same as an active ingredient.

[Means for solving problems]

As a result of intensive research to solve the above-mentioned problems, the present inventors discovered that a new pyrazole oxime derivative has strong insecticidal, acaricidal, and bactericidal activities, and completed the present invention.

That is, the present invention provides (1) the following formula: (wherein R1 is a hydrogen atom, a halogen atom, a carbon atom number of 1
~5 alkyl group; R2 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, R3 represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, a carbon atom number 3 to 5 alkynyl group or optionally substituted aralkyl group; R4 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; n represents an integer of 1 to 3; A is the number of carbon atoms It represents an alkylene group of 1 to 5; X represents an oxygen atom or a sulfur atom. ) Compound (2) An insecticide containing the compound of (1) above as an active ingredient
This relates to acaricides and fungicides.

The present invention will be explained in detail below.

In the novel pyrazole oxime derivative (1) which is the target compound, the alkyl group having 1 to 5 carbon atoms is a linear or branched alkyl group (for example, methyl, ethyl, propyl, isopropyl, butyl). , isobutyl, 5ec-butyl, t-butyl, pentyl, isopentyl, neopentyl, etc.).

As the alkyl group having 1 to 8 carbon atoms, linear or branched alkyl groups (in addition to the alkyl groups exemplified above,
Examples include hexyl, 3-methylhexyl, 2-ethylhexyl, heptyl, octyl, etc.).

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

The halo-lower alkyl group includes an alkyl group having 1 to 2 carbon atoms substituted with 1 to 3 halogen atoms (for example,
Chloromethyl, fluoromethyl, trifluoromethyl,
1-chloroethyl, 2-chloroethyl, 1-fluoroethyl, 2-fluoroethyl, etc.).

Examples of alkenyl groups having 3 to 5 carbon atoms include linear or branched alkenyl groups (for example, allyl, 1-propenyl, 1-butenyl, 2-7'tenyl, 1-methylallyl, 2-methylallyl, 2-methylallyl, -pentenyl, isoprenyl, etc.).

Examples of the alkynyl group having 3 to 5 carbon atoms include linear or branched alkynyl groups (e.g., 1-provinyl, 2-provinyl,
-propynyl, 2-butynyl, etc.).

Examples of the aralkyl group include benzyl, 2phenethyl, 4-chlorobenzyl, 4-fluorobenzyl, 4-
Methylbenzyl, 3,4-dichlorobenzyl, 2,4-
Examples include difluorobenzyl.

Examples of alkylene groups having 1 to 5 carbon atoms include linear or branched alkylene groups (e.g., methylene, ethylene,
trimethylene, l-methylethylene, 2-methylethylene, tetramethylene, dimethylmethylene, pentamethylene, etc.).

R1 is a hydrogen atom, a halogen atom, a carbon atom number of 1
-5 alkyl groups, alkoxy groups having 1 to 5 carbon atoms, haloalkyl groups having 1 to 5 carbon atoms, etc., but preferably hydrogen atoms, halogen atoms, and alkyl groups having 1 to 5 carbon atoms. Good base. More preferably, the halogen atom is a fluorine atom or a chlorine atom, and the alkyl group having 1 to 5 carbon atoms is a methyl group.

Examples of R2 include a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and a halogen atom, but preferably a hydrogen atom and an alkyl group having 1 to 5 carbon atoms.
More preferably, the alkyl group having 1 to 5 carbon atoms is a methyl group.

Examples of R3 include an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an optionally substituted aralkyl group, etc. Preferably, an alkyl group having 1 to 4 carbon atoms (for example, methyl, ethyl, propyl, isopropyl, etc.), an alkenyl group having 3 carbon atoms (for example, allyl), an alkynyl group having 3 carbon atoms (for example, 2
-propynyl, etc.), and optionally substituted aralkyl groups (eg, benzyl group, etc.).

Examples of R4 include a hydrogen atom and an alkyl group having 1 to 5 carbon atoms. And the number of carbon atoms is 1~
The alkyl group in 5 is preferably a methyl group or an ethyl group.

Examples of A include alkylene groups having 1 to 5 carbon atoms, preferably alkylene groups having 1 to 2 carbon atoms (eg, methylene, ethylene, etc.).

Examples of X include an oxygen atom and a sulfur atom.

n represents an integer of 1 to 3 when R2 is an alkyl group having 1 to 5 carbon atoms, preferably 1 or 2.

The novel pyrazole oxime derivative (1), which is the target compound, has eight forms (syn form) and two forms (anti form).
, a mixture of 8 bodies and 2 bodies, and furthermore,
Mention may also be made of optical isomers based on asymmetric carbon atoms.

That is, the most preferable target compound (1) of the present invention is CHs R (wherein R1 represents a hydrogen atom, a fluorine atom, a chlorine atom, or a methyl group + R2 represents a hydrogen atom or a methyl group; R1 is a carbon atom Represents an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 carbon atoms, an alkynyl group having 3 carbon atoms, or an optionally substituted aralkyl group; R4 represents a hydrogen atom, a methyl group, or an ethyl group; A represents Represents an alkylene group having 1 to 2 carbon atoms; X represents an oxygen atom or a sulfur atom; n is 1.2
represents. ) can be mentioned.

The object compound (1) of the present invention can be produced, for example, by the following formula (three examples of production methods are shown below).

(Hereafter, blank space) (Manufacturing method 1) (n) (II[) (wherein, Rh , Rz , Rs , R4, n, A and X
has the same meaning as above, and Y represents a leaving group. ) The leaving group Y of the starting compound (m) is not particularly limited, and includes, for example, a halogen atom (chlorine, bromine, iodine, etc.)
, alkylthio groups (methylthio, ethylthio, propylthio, butylthio, etc.), alkanesulfonyloxy groups optionally substituted with halogen (methanesulfonyloxy, ethanesulfonyloxy, trifluoromethanesulfonyloxy, etc.), arylsulfonyloxy groups (
benzenesulfonyloxy, p-toluenesulfonyloxy, etc.), hydroxyl group, etc., but preferably a halogen atom.

Starting compound (II) is, for example, C1A, 1970.7
Formyl compound (I) synthesized by the method described in 3.3844-
V) to J,Org,Ches+,,14,783(
1949), J, A+w, Chea+, Soc, +6
According to the method described in 9.1803 (1947), it can be easily synthesized as follows.

(Hereinafter, blank spaces) (IV) (V) (II) (In the formula, R and R4 have the same meanings as above.) The raw material compound (III) is, for example, Organic 5yntheses, Co11ec
tive Volume 1 +435 (19
According to the method described in 41), it can be easily produced by performing the following formula.

(Hereinafter, blank space) (Vl) (In the formula, Rz, Rs, A, ) in a solvent in the presence of a base, but it can also be produced by reacting the starting compound (n) and (I[ ) can also be obtained by heating and dissolving and reacting.

The solvent is not particularly limited as long as it is not directly involved in this reaction, and examples include benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform, and dichloroethane. chlorinated or non-chlorinated aromatic, aliphatic, cycloaliphatic hydrocarbons such as , trichlorethylene, cyclohexane; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.; acetone, methyl ethyl ketone, etc. Ketones; alcohols such as methanol, ethanol, ethylene glycol, etc. or their hydrates, N, N
- amides such as dimethylformamide, N,N-dimethylacetamide, etc.; organic bases such as pyridine, N,N-diethylaniline, etc.; 1,3-dimethyl-2
-imidazolidinone; dimethyl sulfoxide; mixtures of the above solvents, and the like.

When the reaction is carried out using a two-phase mixed solvent, it is preferable to use a phase transfer catalyst such as triethylbenzylammonium chloride, triethylbenzylammonium bromide, tetrabutylammonium chloride, tetrabutylammonium bromide, trioctylmethylammonium chloride, or the like.

Examples of the base include triethylamine, pyridine,
Organic bases such as N,N-diethylaniline, etc.; Alkali metal alkoxides such as sodium methoxide, sodium ethoxide, etc.; sodium amide, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, sodium hydride, etc. Examples include inorganic bases.

The method for producing target compound (I) requires a reaction concentration of 5 to 100%.
It can be done with

In the production method, the raw material compound (II) and (■) are used at a ratio of 0.5 to 1.5 mol per 1 mol of the raw material compound (■). However, it is preferably 0.5 to 1.0 mol.

The reaction temperature is not particularly limited as long as it is carried out below the boiling point of the solvent used, but it can usually be carried out above room temperature.
It is preferable to shorten the reaction time by heating.

The reaction time varies depending on the concentration and temperature mentioned above, but it can usually be carried out for 2 to 10 hours.

The target compound (1) can be appropriately purified by known means such as recrystallization and various types of chromatography. The acid addition salt thereof can be easily obtained, for example, by introducing an acid into the reaction solution after the reaction is completed, and then removing the solvent.

(Manufacturing method 2) (V) (■) CH.

1 (IJ (wherein Rr, Rz, R3, R4, n, A and X have the same meanings as above) The raw material compound (■) is, for example,
rOrganischen Che+wie(Hobe
n weyl)BandX/1stickstoffv
erbindungen Tel I, p. 11
According to the method described in No. 92, it can be easily manufactured by performing the following formula.

(III) (■) (In the formula, R,,R,,A,
It can be obtained by reacting in the same manner as in the production method using (V) in place of II) and (■) in place of the starting compound (DI).

(Production method 3) (In the formula, R1, R2, R3, R4, and Y have the same meanings as above.) 1 1 n and the target compound (1) are the starting material compound (
Using (VI[I) instead of II), starting compound (I
It can be obtained by reacting in the same manner as in Production Method 1 using (IX) instead of [I].

Compounds (1) of the present invention are found to have a controlling effect on agricultural and horticultural pests [e.g., Hemiptera (planthoppers such as the brown planthopper, leafhoppers such as the black leafhopper, aphids, whiteflies, etc.); Lepidoptera; (e.g., fall armyworms, mealybugs, leaf beetles, caterpillars, cabbage moths, etc.); Acarinae (e.g., citrus spider mites, two-spotted spider mites, etc.); Coleoptera (e.g., cutworms, mealworms, potato beetles)], disease-causing bacteria (e.g., Cucumber mildew, cucumber gray mold, wheat rust, rice blast, barley powdery mildew), sanitary pests (e.g. flies, flies, cockroaches, etc.), nematodes in the soil (e.g. sweet potato nematode, etc.), Examples include pine tree nematode and nematode.

The insecticide/bactericide of the present invention contains one or more compounds (1) as an active ingredient.

Compound (1) can be used alone, but it is usually mixed with carriers, surfactants, dispersants, adjuvants, etc. (for example, powders, emulsions, fine granules, granules, hydrated It is preferable to prepare a composition such as a drug, an oily suspension, an aerosol, etc.).

Examples of carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea; hydrocarbons (kerosene, mineral oil, etc.), aromatic hydrocarbons (
benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene glycol acetate, etc.) , dibutyl maleate, etc.), alcohols (methanol, n-
hexanol, ethylene glycol), polar solvents (
dimethylformamide, dimethyl sulfoxide, etc.),
Examples include liquid carriers such as water; gas carriers such as air, nitrogen, carbon dioxide, and freon (in this case, they can be mixed and injected).

Examples of surfactants and dispersants that can be used to improve properties such as adhesion to animals and plants, absorption, dispersion, emulsification, and spreading of drugs include alcohol sulfate esters, alkyl sulfonates, lignin sulfonate,
Examples include polyoxyethylene glycol ether.

In order to improve the properties of the preparation, carboxymethyl cellulose, polyethylene glycol, gum arabic, etc. can be used as adjuvants.

In the standard production, the carrier, surfactant, dispersant, and auxiliary agent described above may be used alone or in appropriate combinations depending on the purpose.

When the compound (1) of the present invention is formulated, the concentration of the active ingredient is usually 1 to 50% by weight in an emulsion, and usually 0.3% in a powder.
-25% by weight, usually 1-90% by weight for wettable powders, usually 0.5-5% by weight for granules, usually 0.5-5% by weight for oils, and usually 71-5% by weight for aerosols.

These preparations can be diluted to an appropriate concentration and sprayed on plant foliage, soil, or the water surface of paddy fields, depending on the purpose.
Alternatively, it can be applied directly for various purposes.

〔Example〕

The present invention will now be illustrated by examples. Note that these Examples do not limit the scope of the present invention.

Example 1 [l,3-dimethyl-5-phenoxypyrazole-4-
Formaldoxime 0-2- (Synthesis of 4-(2-methoxyethyl)phenoxyethyl ether) 1,3-dimethyl-5phenoxypyrazole-4-formaldoxime (1,1 g,
5.0 mmof) and the starting compound (I[I) 2-(
4-(2-methoxyethyl)phenoxyphethyl bromide (1.3 g, 5.0 m m .

Dissolve rito in dimethyl sulfoxide (30ml),
Potassium hydroxide (0.4 g) was added while stirring at room temperature, and the mixture was further stirred at room temperature for 5 hours.

After the reaction was completed, water was added and the oily substance separated was extracted with ethyl acetate. This was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.

The obtained oil was subjected to silica gel column chromatography (Wakogel C-200, hexane:ethyl acetate-5:
1 elution) to obtain 1.5 g of target compound (I) (compound number 1) as a colorless oil.

Example 2 [1,3-dimethyl-5-(4-fluorophenoxy)
Pyrazole-4-formaldoxime 0-2- (4-
1,3-dimethyl-5(4-
Fluorophenoxy) pyrazole-4-formaldoxime (1.2 g, 5.1 mmof) and starting compound (II
I) 2-[4-(2-ethoxyethyl)phenoxy]ethyl bromide (1.4 g, 5.1 mmof) was dissolved in dimethylformamide (30 mj2), and potassium hydroxide (0, 4g) was added thereto, and the mixture was further stirred at room temperature to 40°C for 4 hours.

After the reaction was completed, water was added and the oily substance separated was extracted with ethyl acetate. This was washed with water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.

The obtained oil was subjected to silica gel column chromatography (Wako, Gel C-200, hexane:ethyl acetate-5).
:1 elution) to obtain 1.6 g of the target compound (■) (Compound No. 2) as a colorless oil.

Examples 3 to 38 In Example 2, starting compound (II) (note that R and R4 have the same meanings as shown in Table 1) and starting compound (III) (note that R, , R, X, Y, A and n are synonymous with those shown in Table 1.) By carrying out the same procedure as in Example 2, the first
The target compound (I) shown in the table (the numbers of the obtained compounds are shown as numbers 3 to 3B corresponding to the examples. Also, as a comparative example for the compound of the present invention, JP-A No. 63-18
The compound described in Publication No. 3564 was also described. ) was obtained.

(Hereinafter, blank space) Example 39 [Preparation of granules] 5 parts by weight of compound No. 1 (compound of Example 1),
35 parts by weight of bentonite, 57 parts by weight of talc, 1 part by weight of Neoperex powder (trade name; manufactured by Kao Atlas Co., Ltd.) and 2 parts by weight of lignin sulfonic acid were mixed uniformly, and then a small amount of water was added and kneaded. The granules were dried to obtain granules.

Example 40 [Preparation of hydrating agent] 10 parts by weight of compound No. 4 (compound of Example 4), 70 parts by weight of kaolin, 18 parts by weight of white carbon,
Neoperex powder (product name; manufactured by Kao Atlas) 1
．． 5 parts by weight and Demol (product name; manufactured by Kao Atlas) 0
．． 5 parts by weight were uniformly mixed and then ground to obtain a wettable powder.

Example 41 [Preparation of emulsion] Add 20 parts by weight of Compound No. 4, 70 parts by weight of xylene, and 10 parts by weight of toxanone (trade name; manufactured by Sanyo Chemical Industries, Ltd.), mix uniformly, and dissolve to obtain an emulsion. Ta.

Example 42 [Preparation of powder] 5 parts by weight of Compound No. 6, 50 parts by weight of talc, and 45 parts by weight of kaolin were uniformly mixed to obtain a powder.

Example 43 [Efficacy test against diamondback moth] The target compound shown in Table 1 prepared according to Example 40 (
Each of the hydrating agents in 1) was diluted to 50 ppm with water containing a surfactant (0.01%), each cabbage leaf piece (5 cm x 5 cm) was immersed in each of these chemical solutions for 30 seconds, and after air drying, I put one in each plastic cup.

Then, 10 3rd instar diamondback moth larvae were placed in each cup, the cup was covered with a lid, and the cup was left in a thermostatic chamber at 25° C. for 2 days.The number of live and dead insects in each cup was counted to determine the mortality rate.

Evaluation of drug effects is divided into four stages (A) depending on the range of mortality rate.
: 100%, B: 99-80%, c-near 9-60%, D
:59% or less).

The results are shown in Table 2.

Table Example 44 [Efficacy test against black leafhopper] Each hydrating agent of the target compound (1) shown in Table 1 prepared according to Example 40 was added to 1100 pp of water containing a surfactant (0.01%).
Each rice seedling was immersed in each of these chemical solutions for 30 seconds, air-dried, and then inserted into each glass cylinder.

Then, 10 4th instar leafhopper larvae were released into each cylinder and the cylinders were sealed with porous plugs, and kept at 25°C for 4 days.
The number of live and dead insects in each cylinder was counted to determine the mortality rate.

The results are shown in Table 3 using the four-stage evaluation method described in Example 43.

Table 3 Example 45 [Efficacy test against adult two-spotted spider mites] Each hydrating agent of the target compound (1) shown in Table 1 prepared according to Example 40 was prepared using a surfactant (0.01%). Each green bean leaf piece (diameter 20 mm) infested with 10 female adult two-spotted spider mites diluted with water to 30 ppm and 10 ppm was soaked in each of the chemical solutions (30 ppm and 10 ppm) for 15 seconds.

Next, each of these leaf pieces was left in a constant temperature room at 25°C for 3
Days later, the number of live and dead insects on each leaf was counted to determine the acaricidal rate.

The results are shown in Table 4 [The comparative drugs used were:
Compounds listed in the Comparative Examples column of Table 1
The compound described in Japanese Patent No. 183564) was prepared in the same manner. ].

Table 1 Example 46 [Efficacy test against adult female citrus spider mite] Each hydrating agent of the target compound (1) shown in Table 1 prepared according to Example 40 was added to water containing a surfactant (0.01%). at 10ppm
and 3 ppm, and 5 ml of these solutions (10 ppm and 3 ppm) were sprayed on each mulberry leaf piece (2 Q mm in diameter) infested with 10 female adult citrus spider mites.

Next, each of these leaf pieces was left in a constant temperature room at 25°C for 3
After a day, the number of live and dead insects on each mulberry leaf was counted to determine the acaricidal rate.

The results are shown in Table 5 (the comparative drugs used were:
The compounds listed in the Comparative Examples column of Table 1 were prepared in the same manner. ).

Table 5 Comparative agent 0 Example 47 [Control efficacy test (preventive effect) against rice blast] Ten rice plants (variety: Nipponbare) were grown per pot in plastic flower pots with a diameter of 6 cm, and rice plants (variety: Nipponbare) were grown at the 1.5 leaf stage. Each hydrating agent of the target compound (1) shown in Table 1 prepared according to Example 40 was diluted to 500 ppm with water containing a surfactant (0.01%) on a young plant. 20mf per pot
It was dispersed.

After spraying, the rice blast fungus (Pyricularia
oryzae) conidial suspension (7X10'spores/m
i,) was uniformly spray inoculated onto the plant leaves.

After inoculation, the plants were grown in a humid room at 28°C for 5 days, and the extent of rice blast lesions that appeared on the leaves was examined.

The drug effect was evaluated by comparing the degree of lesions in the untreated area.
6 stages (0: whole disease affected, 1: lesion area approximately 60%,
2: Lesion area is approximately 40%, 3: Lesion area is approximately 20%, 4: Lesion area is 10% or less, 5: No lesion).

The results are shown in Table 6 (the comparative drugs used were
The compounds listed in the Comparative Examples column of Table 1 were prepared in the same manner. ).

Table 1 Comparative drugs 0 No treatment 0 Example 48 [Control efficacy test (preventive effect) against barley powdery mildew] Ten barley plants (variety: black wheat) were grown per pot in plastic flower pots with a diameter of 6 cm, and Example 40 The target compound (I) shown in Table 1 was added to the seedlings at the 5-leaf stage.
Each hydrating agent prepared according to
) diluted to 500 ppm with water containing 20 per pot.
mj! It was dispersed.

After spraying, the barley powdery mildew fungus (Erysiphe) was cultivated in a glass greenhouse for 2 days, and then infected with barley powdery mildew (Erysiphe) prepared from diseased leaves.
A conidial suspension of C. graminis was evenly sprinkled onto the plant to inoculate it.

After inoculation, the plants were grown in a glass greenhouse for one week, and the extent of barley powdery mildew lesions that appeared on the first leaves was examined.

The results of the evaluation of the drug effect are shown in Table 7 using the same evaluation method as in Example 47 (the comparative drugs used are
The compounds described in the Comparative Examples column in the table were prepared in the same manner. ).

(Hereinafter, blank space) Table 1 Comparative No chemical treatment 0 [Effects of the Invention] The present invention can provide pyrazole oxime derivatives having excellent insecticidal, acaricidal, and bactericidal effects.

Claims (2)

[Claims] (1) The following formula: ▲ Numerical formulas, chemical formulas, tables, etc. Represents an alkyl group of number 1 to 5; R_3 has 1 carbon atom
-8 alkyl group, alkenyl group having 3 to 5 carbon atoms,
Represents an alkynyl group having 3 to 5 carbon atoms or an optionally substituted aralkyl group; R_4 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; n represents an integer of 1 to 3;
A represents an alkylene group having 1 to 5 carbon atoms; X represents an oxygen atom or a sulfur atom. ). (2) An insecticidal, acaricidal, and bactericidal agent containing the compound of formula (I) according to claim 1 as an active ingredient.