JP6685600B2 - Heating transpiration agent for mosquito control - Google Patents

Description

The present invention relates to a use of a pyrethroid compound having a heat transpiration property as a mosquito control agent.

Currently, pyrethroid insecticides such as allethrin and prarethrin are used as active ingredients of mosquito coil (see Non-Patent Document 1). However, the control efficacy against these mosquitoes is not always satisfactory. Patent Document 1 describes a fluorobenzyl ester, a method for producing the same, and an insecticide composition containing the same as an active ingredient. However, Patent Document 1 does not make sufficient evaluation of insecticidal activity against mosquitoes.

JP-A-64-66146

"Continued Drug Development Vol. 18 Pesticide Development III", Hirokawa Shoten, 1993, p. 493

An object of the present invention is to provide a mosquito control heating transpiration agent using a novel pyrethroid mosquito control component having heat transpiration property, and a mosquito control method using the same.

As a result of intensive studies, the present inventors have found that an ester compound represented by the following general formula [Chemical formula 1] has an excellent controlling effect against mosquitoes based on heat transpiration, and completed the present invention. It was

That is, the present invention relates to the following inventions.
(1) General formula [Chemical formula 1]
[In the formula, R represents a methyl group. ] A heat-transpiration agent for mosquito control, which comprises an ester compound represented by
(2) A mosquito control method using the heated transpiration agent for mosquito control according to (1) .
(3) General formula [Chemical formula 1]
[In the formula, R represents a methyl group. ] A mosquito coil which contains the ester compound shown by these as an active ingredient.
(4) A method for controlling mosquitoes using the mosquito coil according to (3) .

INDUSTRIAL APPLICABILITY Since the compound of the present invention has heat transpiration property and further has excellent control effect against mosquitoes, it is useful as an active ingredient of a heat transpiration agent for mosquito control.

The compounds of the present invention include optical isomers derived from the two asymmetric carbon atoms present at the 1-position and 3-position on the cyclopropane ring, and the 1'-position present on the substituent at the 3-position of the cyclopropane ring. Although there are isomers derived from the double bond, the present invention includes each isomer having pest control activity and a mixture of isomers in any ratio.

The forms of the compound of the present invention include the following.
General formula [Chemical formula 2]
In the compound of the present invention represented by
A compound whose absolute configuration at the 1-position of the cyclopropane ring is R configuration;
A compound in which the relative configuration of the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is the trans configuration.
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is the cis configuration;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration, and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is the trans configuration;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is the trans configuration;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is the trans configuration is 80% or more. ;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the R configuration and the relative configuration between the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is the trans configuration is 90% or more. .

Next, a method for producing the compound of the present invention will be described.
The compound of the present invention is not particularly limited as long as it is a method for producing an ordinary ester compound, but can be produced, for example, by the method shown below.
(Production method 1)
Formula [Formula 3]
An alcohol compound represented by
Formula [Formula 4]
[In the formula, R represents a methyl group or a chlorine atom. ] The compound of the present invention is obtained by reacting with a carboxylic acid compound represented by or a reactive derivative thereof.

Examples of the reactive derivative include an acid halide of a carboxylic acid compound represented by [Chemical Formula 4], an acid anhydride of the carboxylic acid compound, and an ester of the carboxylic acid compound. Examples of the acid halide include acid chloride compounds, and examples of the ester include methyl ester and ethyl ester.
The reaction is usually performed in a solvent in the presence of a condensing agent or a base.
Examples of the condensing agent include dicyclohexylcarbodiimide and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, and
Examples of the base include organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine and diisopropylethylamine.
Examples of the solvent include hydrocarbons such as toluene and hexane, ethers such as tetrahydrofuran, esters such as ethyl acetate, halogenated hydrocarbons such as chlorobenzene, and mixed solvents thereof.

In the reaction, the molar ratio of the alcohol compound represented by the formula [Chemical formula 3] and the carboxylic acid compound represented by the formula [Chemical formula 4] or a reactive derivative thereof can be arbitrarily set, but is preferably equimolar. Or a ratio close to it.
The condensing agent or base can be usually used in an arbitrary ratio from 0.25 mol to an excess amount, preferably 0.5 mol, per 1 mol of the alcohol compound represented by the formula [Chemical Formula 3]. ~ 2 moles. These condensing agents or bases are appropriately selected depending on the kind of the carboxylic acid compound represented by the formula [Chemical Formula 4] or its reactive derivative.
After completion of the reaction, the reaction mixture may be filtered to concentrate the filtrate, or may be subjected to a conventional post-treatment operation such as extraction with an organic solvent and concentration after pouring it into water to give the compound of the present invention. Obtainable. The obtained compound of the present invention can be purified by operations such as chromatography and distillation.

The alcohol compound represented by the formula [Chemical Formula 3] is a known compound described in JP-A-64-66146 , and can be produced by the method described in the document.
On the other hand, the carboxylic acid compound represented by the general formula [Chemical Formula 4] or its reactive derivative is a known compound, and a commercially available product can be purchased and used.

Examples of the heat-transpiration agent for controlling mosquitoes of the present invention include heat-transpiration agents such as mosquito coil, mosquito mat, mosquito liquid and smoke agent.

Examples of the formulation method include the following methods.
(1) A method of mixing the compound of the present invention with a solid carrier, a liquid carrier or the like, and optionally adding and processing a surfactant or other auxiliary agent for formulation.
(2) A method of impregnating a base material containing no active ingredient with the compound of the present invention.
(3) A method of molding after mixing the compound of the present invention and the substrate.
These formulations usually contain 0.001 to 98% by weight of the compound of the present invention, depending on the formulation form.

Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fubasami clay, acid clay, etc.), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (serisite, activated carbon, carbonic acid). Fine powder and granules such as calcium, silica, etc., substances that are solid at room temperature (2,4,6-triisopropyl-1,3,5-trioxane, naphthalene, p-dichlorobenzene, camphor, adamantane, etc.), and Wool, silk, cotton, hemp, pulp, synthetic resin (for example, polyethylene resin such as low density polyethylene, linear low density polyethylene, high density polyethylene; ethylene-vinyl ester copolymer such as ethylene-vinyl acetate copolymer) Ethylene such as ethylene-methyl methacrylate copolymer, ethylene-ethyl methacrylate copolymer -Methacrylic acid ester copolymer; ethylene-acrylic acid ester copolymer such as ethylene-methyl acrylate copolymer, ethylene-ethyl acrylate copolymer; ethylene-vinyl carboxylic acid such as ethylene-acrylic acid copolymer Copolymers; polypropylene-based resins such as polypropylene and propylene-ethylene copolymers; poly-4-methylpentene-1, polybutene-1, polybutadiene, polystyrene; acrylonitrile-styrene resin; acrylonitrile-butadiene-styrene resin, styrene-conjugated Styrene-based elastomers such as diene block copolymers and styrene-conjugated diene block copolymers hydrogenated products; fluororesins; acrylic resins such as polymethylmethacrylate; polyamide resins such as nylon 6 and nylon 66; polyethylene terephthalate Polyester resins such as rate, polyethylene naphthalate and polybutylene terephthalate; polycarbonate, polyacetal, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, polyurethane, Porous resin such as polyurethane foam, polypropylene polypropylene, and ethylene foam), felt, fiber, cloth, knitted fabric, sheet, paper, thread, foam, porous body made of one or more of glass, metal, ceramic, etc. And multifilaments.

Examples of the liquid carrier include aromatic or aliphatic hydrocarbons (xylene, alkylnaphthalene, phenylxylylethane, kerosene, light oil, hexane, cyclohexane, etc.), alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl). Alcohol, ethylene glycol, etc.), ethers (diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, tetrahydrofuran, etc.), esters (ethyl acetate, butyl acetate, etc.), ketones (acetone) , Methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), nitriles (acetonitrile, isobutyronitrile) Etc.), sulfoxides (dimethyl sulfoxide etc.), acid amides (N, N-dimethylformamide, N-methyl-pyrrolidone etc.), alkylidene carbonates (propylene carbonate etc.), vegetable oils (soybean oil, cottonseed oil etc.), plant essential oils (Orange oil, hyssop oil, lemon oil, etc.), and water.

Examples of the surfactant include alkyl sulfate ester salts, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyoxyethylene compounds of alkyl aryl ethers, polyethylene glycol ethers, polyhydric alcohol esters and sugars. Examples include alcohol derivatives.

Other auxiliaries for formulations include fixing agents, dispersants, stabilizers, and the like, specifically, casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, With synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone), polyacrylic acid, BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (2-tert-butyl-4-methoxyphenol) A mixture with 3-tert-butyl-4-methoxyphenol). Further, a coloring agent, a fragrance, or the like may be appropriately blended if necessary.

Examples of the base material of the mosquito coil include a mixture of vegetable powder such as wood powder and pyrethrum extracted lees and a binder such as tab powder, starch, carboxymethyl cellulose and gluten.
Examples of the base material of the mosquito repellent mat include those obtained by hardening cotton linter into a plate shape, and those obtained by hardening a filible of a mixture of cotton linter and pulp into a plate shape.
Examples of base materials for self-burning smoke agents include heat-generating agents such as nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethyl cellulose, wood flour, and other heat-generating agents, alkali metal salts, and alkaline earth metal salts. Examples thereof include a decomposition stimulant, an oxygen supply agent such as potassium nitrate, a combustion support agent such as melamine and wheat starch, an extender agent such as diatomaceous earth, and a binder such as a synthetic paste.

Examples of the base material of the chemical reaction type smoke agent include alkali metal sulfides, polysulfides, hydrosulfides, exothermic agents such as calcium oxide, iron carbide, catalyst agents such as activated clay, azodicarbonamide, and benzene. Examples thereof include organic foaming agents such as sulfonyl hydrazide, dinitropentamethylenetetramine, polystyrene and polyurethane, and fillers such as natural fiber pieces and synthetic fiber pieces.

Examples of the resin used as the base material for the resin vaporizing agent include polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymer. Polymer; ethylene-methacrylic acid copolymer, ethylene-methacrylic acid ester copolymer such as ethylene-ethyl methacrylate copolymer; ethylene-methyl acrylate copolymer, ethylene-ethyl acrylate copolymer, etc. Ethylene-acrylic acid ester copolymer; ethylene-vinyl carboxylic acid copolymer such as ethylene-acrylic acid copolymer; polypropylene-based resin such as polypropylene and propylene-ethylene copolymer; poly-4-methylpentene-1, Polybutene-1, polybutadiene, polystyrene, acrylonitrile Styrene resin; Acrylonitrile-butadiene-styrene resin, styrene-conjugated diene block copolymer, styrene-conjugated diene block copolymer Styrene elastomer such as hydrogenated product; Fluorine resin; Acrylic acid resin such as polymethylmethacrylate; Nylon Polyamide resins such as 6, nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene phthalate; polycarbonate, polyacetal, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, poly Examples thereof include vinyl chloride, polyvinylidene chloride, and polyurethane. These base materials may be used alone or as a mixture of two or more kinds. Phthalates necessary to (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, plasticizers such as stearic acid may be added. The resin transpiration agent can be obtained by kneading the compound of the present invention in the above-mentioned base material, and then molding by injection molding, extrusion molding, press molding or the like. The obtained resin preparation can be further processed into a plate shape, a film shape, a tape shape, a net shape, a string shape or the like by further undergoing steps such as molding and cutting. These resin preparations are processed, for example, as non-heated transpiration agents, animal collars, animal ear tags, sheet preparations, attracting tapes, attracting strings, and horticultural supports.

The compound of the present invention can also be used in combination or in combination with other insecticides, acaricides, fungicides, herbicides, repellents, synergists, fertilizers and soil conditioners.

As the active ingredient of such insecticides and acaricides, for example,
[1] Pyrethroids Pyrethrins, Allethrins, Prallethrins, Furamethrins, Resmethrins, Tetramethrins, Tetramethrins, Imiprothrins, Imiprothrins, Imiprotrins, and Imiprotrins transfluthrin, metofluthrin, profluthrin, phenothrin, cyphenothrin, permethrin, cypermethrin, cypermethrin. hrin), beta-cyfluthrin, fenpropathrin, bifenthrin, cycloprothrin, deltamethrin, deltamethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin, flumethrin. , Cyhalothrin, lambda cyhalothrin, lamda-cyhalothrin, tefluthrin, fenvalerate, fluvalinate, etofenprox, silafluofi. afluofen), Mont fluoro Trinh (momfluorothrin), dimefluthrin (dimefluthrin) or the like;
[2] Organophosphorus compound acephate, butathiophos, diazinon, dichlorvos (DDVP), dimethoate (dimethoate), fenthion (phenthion: MPP), fenitrothion (feition). malathion), pyridafenthion, propaphos, trichlorfon (DEP) and the like;
[3] Carbamate compounds Carbaryl (carbary1), carbofuran (carbofuran), fenobucarb, isoprocarb (isoprocarb: MIPC), mesomil (methoyl), NAC, propoxur (propoxur: PHC) and the like;
[4] Nereistoxin-based compound cartap, bensultap, etc .;
[5] Neonicotinoid compounds Imidacloprid (imidac1oprid), nitenpyram, acetamiprid, thiamethoxin, thiacloprid, clothifuran, dinotefuran (dinotefuran), dinotefuran (dinothefuran)
[6] Benzoylurea Compound Chlorfluazuron, Bistrifluron, Diflubenzuron, Flufenoxuron, Hexaflumulon, Teflubenzuron, Teflubenzuron, Teflubenzuron, Teflubenzuron etc;
[7] Phenylpyrazole-based compound fipronil (fiproni1), pyriprole, pyrafluprole, etc .;
[8] Hydrazine compound Chromafenozide, halofenozide, methoxyphenozide, etc .;
[9] Natural insecticide machine oil (machine oil), nicotine sulfate (nicotine-sulfate);
[10] Other insecticides avermectin-B, buprofezin, chlorphenapyr, hydroprene, methoprene, methoprene, indoxacardia, indoxacardia, metoprene, metoprene. milbemycin-A), pyridalyl (pyridalyl), pyriproxyfen (pyriproxyfen), spinosad (spinosad), Surufuramido (sulfluramid), tolfenpyrad (tolfenpyrad), flubendiamide (flubendiamide), cyflumetofen (cyflumetofen), Nioikame Examples include chill (Methyl bromide) and potassium oleate (Potassium oleate).

Examples of the active ingredient of the repellent include N, N-diethyl-m-toluamide, limonene, linalool, citronellal, menthol, menthone, hinokitiol, geraniol, p-menthane-3,8-diol, eucalyptol, caran-3. , 4-diol, IR-3535, MGK-R-326, MGK-R-874, KBR-3023 and the like.

Examples of the active ingredient of the synergist include 5- [2- (2-butoxyethoxy) ethoxymethyl] -6-propyl-1,3-benzodioxole and N- (2-ethylhexyl) bicyclo [2.2]. .1] Hept-5-ene-2,3-dicarboximide, octachlorodipropyl ether, isobornyl thiocyanoacetate, N- (2-ethylhexyl) -1-isopropyl-4-methylbicyclo [2.2. 2] Oct-5-ene-2,3-dicarboximide and the like.

Examples of mosquitoes to which the heat-transpiration agent of the present invention is effective include mosquitoes such as Culex pipiens and Culex pipiens, mosquitoes such as Aedes aegypti and Aedes albopictus, anopheles such as Aedes albopictus, and midges.

The mosquito control method of the present invention is carried out by applying an effective amount of the compound of the present invention to a mosquito or a mosquito habitat, usually in the form of the pest control agent of the present invention.
Examples of the method of applying the mosquito control agent of the present invention include a method of volatilizing the active ingredient by heating in a mosquito habitat.
In this case, both the application amount and the application concentration of the compound of the present invention can be appropriately determined according to the form of the mosquito control agent of the present invention, the application time, the application place, the application method, the type of mosquito, the damage situation and the like.

When the compound of the present invention is used for controlling mosquitoes, its application amount is usually 0.001 to 100 mg / m ³ as the amount of the compound of the present invention when applied to a space, and 0.001 when applied to a flat surface. ~ 100 mg / m ² . For mosquito coil and mosquito mat, the active ingredient is volatilized by heating and applied according to the formulation form.
Examples of the space to which the mosquito control agent of the present invention is applied for mosquito control include a living room, a dining room, a bedroom, a Japanese bath, and the like, and it can also be applied in an open outdoor space.

Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, effect test examples, and the like, but the present invention is not limited to these examples.

First, production examples of the compound of the present invention will be shown.
Production example 1
4-ethynyl-2,3,5,6-tetrafluorobenzyl alcohol (100 mg, 0.49 mmol) and (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (141 mg, 0.74 mmol) and 4-dimethylaminopyridine (5 mg) were added to a chloroform solution (5 mL) of an acid (124 mg, 0.74 mmol). . After stirring at room temperature for an hour, water was added to the reaction solution, and this was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to give the compound represented by the following formula [Chemical formula 5].

4-ethynyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate represented by This is referred to as compound A.) 134 mg was obtained.

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.13 (s, 3H), 1.27 (s, 3H), 1.38 (d, 1H), 1.69 (s). , 3H), 1.70 (s, 3H), 2.07 (m, 1H), 3.66 (s, 1H), 4.87 (d, 1H), 5.22 (m, 2H).

Production example 2
4-Ethynyl-2,3,5,6-tetrafluorobenzyl alcohol (55 mg, 0.27 mmol) in a tetrahydrofuran solution (2 mL) was pyridine (106 mg, 1.35 mmol), (1R) -trans-3- (2,2). 2-Dichloro-1-ethenyl) -2,2-dimethylcyclopropanecarboxylic acid chloride (215 mg, 0.36 mmol) and 4-dimethylaminopyridine (4 mg) were sequentially added. After stirring at room temperature for 18 hours, water was added to the reaction solution, and this was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to give the compound represented by the following formula [Chemical formula 6].

4-ethynyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2,2-dichloro-1-ethenyl) -2,2-dimethylcyclopropanecarboxylate represented by Inventive compound B) 64 mg was obtained.

Colorless liquid: ¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.19 (s, 3H), 1.31 (s, 3H), 1.62 (d, 1H), 2.25 (m , 1H), 3.67 (s, 1H), 5.23 (m, 2H), 5.59 (d, 1H).

Next, formulation examples are shown. In addition, a part shows a mass part.

Formulation example 1
After 0.3 g of the compounds A and B of the present invention and 0.5 g of BHT were uniformly stirred and mixed with 99.2 g of a base material for mosquito coil (mixture of pyrethrum extracted lees powder, wood powder, tab powder, and starch), 100 mL of water containing malachite green as a colorant is added, and a sufficiently kneaded product is molded and dried to obtain a mosquito coil.

Formulation example 2
0.8 g of each of the compounds A and B of the present invention, 0.4 g of piperonyl butoxide, and deodorized kerosene were added to the dye and dissolved to make a total volume of 10 mL. 0.5 mL of this solution is uniformly impregnated into a mosquito repellent mat base material (cotton linter / pulp mixture filible hardened into a plate) having a thickness of 22 mm × 35 mm and a thickness of 2.8 mm, to form a mosquito repellent mat agent. To get

Formulation example 3
A liquid agent obtained by dissolving 0.7 parts of each of the compounds A and B of the present invention and 0.3 part of BHT in 50 parts of a surfactant (diethylene glycol monobutyl ether) and 49 parts of purified water was placed in a polyester container, and the upper part was placed. An aqueous mosquito repellent liquid agent used in a heating evaporation device is obtained by inserting a liquid absorbent core (which is obtained by firing an inorganic powder) that can be heated by a heater.

Formulation example 4
100 mg of each of the compounds A and B of the present invention is dissolved in an appropriate amount of acetone and impregnated into a porous ceramic plate having a size of 4 cm × 4 cm and a thickness of 1.2 cm to obtain a heated smoking agent.

Next, it is shown as a test example that the compound of the present invention is effective as an active ingredient of a mosquito control agent.

Effect test example 1 (basic insecticidal activity test against Culex pipiens)
0.05 mL of 0.2% acetone solution containing 0.1 mg of the compound of the present invention [Chemical Formula 5] was dropped on a petri dish having a diameter of 28 mm, an inner height of 13 mm, and a bottom area of 6.15 cm ² so that the bottom surface became uniform. After spreading, remove the acetone with a double ball. Put three females of Culex pipiens into a petri dish holding each sample on the bottom, cover the upper side with perforated film, record the knockdown number every minute, and then record KT ₅₀ (50% knockdown time). And mortality after 24 hours was measured and recorded. For samples showing a predetermined value or more for the knockdown rate, acetone was further added to the 0.2% acetone solution to dilute it 10 times to make a 0.02% acetone solution, and each of the above instruments (dishes) was tested. The method was repeated sequentially.
Also, the following formula [Chem.
4-acetoxymethyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate represented by No. 64-66146, hereinafter referred to as comparative compound C.), the following formula [Chemical formula 8]
4-ethynyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2-fluoro-1-ethenyl) -2,2-dimethylcyclopropanecarboxylate (JP-A-64-66146) Compounds described in the publication, hereinafter referred to as comparative compound D) and allethrin: (RS) -2-methyl-3- (2-propenyl) -cyclopent-2-en-4-one-1-yl (1RS). The same test was performed using -trans, cis-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter referred to as comparative compound E).
The results are shown in Table 1.

As a result of the test, it was found that the compound A of the present invention and the compound B of the present invention exhibited higher knockdown effect and lethal effect on mosquitoes than the comparative compound C, the comparative compound D and the comparative compound E (allethrin). It was

Effect test example 2 (insecticidal activity test with mosquito coil)
About 100 Aedes aegypti adults were released in a 3 m cubic chamber, and 0.1 g of the mosquito coil of the present invention compound A and the present invention compound B obtained in Formulation Example 1 were ignited at both ends and placed in 1 The knockdown number was recorded every minute and the KT ₅₀ (time for 50% knockdown) was measured and recorded.
Further, the same test was performed using Comparative Compound C, Comparative Compound D and Comparative Compound E (allethrin) as comparative controls.
The results are shown in Table 2.

As a result of the test, the mosquito coil which contains the compound A of the present invention and the compound B of the present invention as an active ingredient has a higher knock than that of the comparative compound C, the comparative compound D and the comparative compound E (allethrin). It turned out to show a down effect.

Effect test example 3 (insecticidal activity test against German cockroach)
An oil agent (neothiozole) having a predetermined concentration (see Table 3) of the compound A of the present invention, the comparative compound C and the comparative compound D was prepared. Ten male German cockroaches were placed in a glass container, covered with a metal net, and placed on the bottom of a glass cylindrical container having a diameter of 40 cm and a height of 45 cm. 0.3 ml of the oil solution was sprayed with a spray gun (pressure 1.5 × 10 ⁶ Pa) through a small hole above the glass cylindrical container. The number of knockdowns over time up to 10 minutes later was recorded and the KT ₅₀ (time for 50% knockdown) was measured and recorded.
The results are shown in Table 3.

As a result of the test, the compound A of the present invention showed almost the same knockdown activity as the comparative compound C and the comparative compound D against the German cockroach.

Since the compound of the present invention has an excellent controlling effect against mosquitoes, it is useful as an active ingredient of a heat vaporizing agent for controlling mosquitoes.

Claims (4)

General formula [Chemical formula 1]
[In the formula, R represents a methyl group. ] A heat-transpiration agent for mosquito control, which comprises an ester compound represented by A mosquito control method using the heated transpiration agent according to claim 1 . General formula [Chemical formula 1]
[In the formula, R represents a methyl group. ] A mosquito coil which contains the ester compound shown by these as an active ingredient. A mosquito control method using the mosquito coil according to claim 3 .