JP2017210463A - Heat evaporation agent for mosquito control - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a heat evaporation agent for mosquito control using a novel pyrethroid based mosquito control component exhibiting evaporation by heating, and a mosquito control method using the same.SOLUTION FOR THE PROBLEM: The present invention provides: a heat evaporation agent for mosquito control containing an ester compound represented by the general formula in the figure, where R represents a methyl group or chlorine atom, as an active ingredient; and a mosquito control method using the heat evaporation agent for mosquito control.SELECTED DRAWING: None

Description

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

Currently, pyrethroid insecticides such as allethrin and praretrin are used as active ingredients of mosquito coils (see Non-Patent Document 1). However, the control effect 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 sufficiently evaluate insecticidal activity against mosquitoes.

JP-A 64-66146

“Continued Drug Development Volume 18: Development of Pesticides III”, Yodogawa Shoten, 1993, p. 493

An object of the present invention is to provide a heat transpiration agent for controlling mosquitoes using a novel pyrethroid-based mosquito control component having heat transpiration and a mosquito control method using the same.

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

That is, the present invention relates to the following inventions.
(1) General formula [Formula 1]
[Wherein, R represents a methyl group or a chlorine atom. ] The heat transpiration agent for mosquito control which contains the ester compound shown by this as an active ingredient.
(2) A heat transpiration agent for controlling mosquitoes containing, as an active ingredient, an ester compound in which R is a methyl group in (1).
(3) A heat transpiration agent for controlling mosquitoes containing, as an active ingredient, an ester compound in which R is a chlorine atom in (1).
(4) A mosquito control method using a heat transpiration agent for controlling mosquitoes contained as an active ingredient of the ester compound according to (1) to (3).
(5) A mosquito coil that contains the ester compound according to any one of (1) to (3) as an active ingredient.
(6) A mosquito control method using a mosquito coil that contains the ester compound according to (1) to (3) as an active ingredient.

The compound of the present invention is useful as an active ingredient of a heat transpiration agent for controlling mosquitoes because it has a heat transpiration property and has an excellent control effect against mosquitoes.

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

Examples of the form of the compound of the present invention include the following.
[Formula 2]
In the compound of the present invention represented by
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is the 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 a 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 of the substituent at the 1-position of the cyclopropane ring and the substituent at the 3-position of the cyclopropane ring is a 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 a trans configuration;
A compound rich in that 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 a 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 80% or more ;
A compound in which the absolute configuration at the 1-position of the cyclopropane ring is 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 90% or more .

Next, the manufacturing method of this invention compound is demonstrated.
Although this invention compound will not be specifically limited if it is a method of manufacturing a normal ester compound, For example, it can manufacture by the method shown below.
(Production method 1)
Formula [Chemical Formula 3]
An alcohol compound represented by
Formula [Formula 4]
[Wherein, 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 the formula:

Examples of the reactive derivative include an acid halide of the 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, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride,
Examples of the base include organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, 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 set arbitrarily, but preferably equimolar Or a ratio close to that.
The condensing agent or base can be used in an arbitrary ratio from 0.25 mol to an excess amount with respect to 1 mol of the alcohol compound represented by the formula [Chemical Formula 3], preferably 0.5 mol. ~ 2 moles. These condensing agents or bases are appropriately selected depending on the type of the carboxylic acid compound represented by the formula [Chemical Formula 4] or a reactive derivative thereof.
The reaction mixture after completion of the reaction is filtered to concentrate the filtrate, or poured into water and then subjected to usual post-treatment operations such as organic solvent extraction and concentration, whereby the compound of the present invention is obtained. Can be obtained. 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 No. 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 a reactive derivative thereof is a known compound, and a commercial product can be purchased and used.

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

Examples of the formulation method include the following methods.
(1) A method in which the compound of the present invention is mixed with a solid carrier, liquid carrier or the like, and a surfactant or other formulation adjuvant is added and processed as necessary.
(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 preparations usually contain 0.001 to 98% by weight of the compound of the present invention, depending on the form of preparation.

Examples of solid carriers used in the formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramic, and other inorganic minerals (sericite, activated carbon, carbonic acid). Fine powders and granules such as calcium, silica, etc., solid substances 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 (eg, polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; ethylene-vinyl ester copolymer such as ethylene-vinyl acetate copolymer) Polymer; 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 and ethylene-ethyl acrylate copolymer; Ethylene-vinyl carboxylic acid such as ethylene-acrylic acid copolymer Copolymers; Polypropylene resins such as polypropylene and propylene-ethylene copolymers; poly-4-methylpentene-1, polybutene-1, polybutadiene, polystyrene; acrylonitrile-styrene resins; acrylonitrile-butadiene-styrene resins, styrene-conjugates Styrene elastomers such as diene block copolymers and hydrogenated styrene-conjugated diene block copolymers; fluororesins; acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6 and nylon 66; Polyester resins such as rate, polyethylene naphthalate, polybutylene terephthalate; polycarbonate, polyacetal, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, polyurethane, Felt, fiber, cloth, knitted fabric, sheet, paper, thread, foam, porous body composed of one or more of foamed polyurethane, foamed polypropylene, foamed ethylene, etc.), 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) ), Sulfoxides (dimethylsulfoxide, 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.

Surfactants include, for example, alkyl sulfate esters, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, polyarylethylenes of alkyl aryl ethers, polyethylene glycol ethers, polyhydric alcohol esters and sugars. Examples include alcohol derivatives.

Other formulation adjuvants include fixing agents, dispersants and stabilizers, such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone), polyacrylic acid, etc., BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (2-tert-butyl-4-methoxyphenol) 3-tert-butyl-4-methoxyphenol). Furthermore, a coloring agent, a fragrance | flavor, etc. may be mix | blended suitably as needed.

Examples of the base material of the mosquito coil include a mixture of a vegetable powder such as wood powder and pesticide extracted chrysanthemum powder and a binder such as tab powder, starch, carboxymethylcellulose, and gluten.
Examples of the base material of the mosquito trap include those obtained by solidifying a cotton linter into a plate shape and those obtained by solidifying a fillet of a mixture of cotton linter and pulp into a plate shape.
Examples of the base material of the self-burning smoke agent include nitrate, nitrite, guanidine salt, potassium chlorate, nitrocellulose, ethyl cellulose, wood powder and other combustion exothermic agents, alkali metal salts, alkaline earth metal salt heat Examples include decomposition stimulants, oxygen supply agents such as potassium nitrate, flame retardants such as melamine and wheat starch, bulking agents such as diatomaceous earth, and binders such as synthetic pastes.

Examples of the base material for the chemical reaction type smoke agent include exothermic agents such as alkali metal sulfides, polysulfides, hydrosulfides, and calcium oxide, catalyst agents such as iron carbide and 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 for the substrate such as a resin transpiration agent include polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; and ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymer. Polymer; ethylene-methacrylic acid ester copolymer such as ethylene-methyl methacrylate copolymer, 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 resin such as polypropylene and propylene-ethylene copolymer; poly-4-methylpentene-1, Polybutene-1, polybutadiene, polystyrene, acrylonitrile Styrene resin; Styrenic elastomer such as acrylonitrile-butadiene-styrene resin, styrene-conjugated diene block copolymer, hydrogenated styrene-conjugated diene block copolymer; Fluororesin; Acrylic resin such as polymethyl methacrylate; Nylon 6, polyamide resins such as 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, polyurethane and the like. These substrates may be used alone or as a mixture of two or more. 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 it 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 through steps such as molding and cutting if necessary. These resin preparations are processed, for example, as a non-heated transpiration agent, an animal collar, an animal ear tag, a sheet preparation, an attracting tape, an attracting string, and a garden support.

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

As an active ingredient of such insecticides and acaricides, for example,
[1] Pyrethroid compounds pyrethrins, allethrin, praretrin, furamethrin, resmethrin, tetramethrin, imiprothrin, imiprothrin transfluthrin, methfluthrin, profluthrin, phenothrin, cyphenothrin, permethrin, cypermethrin, cypermethrin, cypermethrin. hrin), beta-cyfluthrin, fenpropathrin, bifenthrin, cycloprotorin, deltamethrin, flumethrin (flumethrin), flumethrin (flumethrin) Cyhalothrin, lambda-cyhalothrin, tefluthrin, fenvalerate, fulvalinate, etofenprox, silaflufens afluofen), Mont fluoro Trinh (momfluorothrin), dimefluthrin (dimefluthrin) or the like;
[2] Organophosphorus compounds Acephate, butathiofos, diazinon, dichlorvos (DDVP), dimethoate, fenthion (MPP), fenitrothion (MEP) malathion), pyridafenthion, propaphos, trichlorphone (DEP) and the like;
[3] Carbamate compounds carbaryl (carbary1), carbofuran, fenobucarb, isoprocarb (MIPC), mesomyl, NAC, propoxur (PHC), etc .;
[4] Nereistoxin compounds Cartap, bensultap, etc .;
[5] Neonicotinoid type compounds Imidacloprid (imidac1oprid), Nitenpyram (nitrenpyram), Acetamiprid (acetamipride), thiamethoxam (thiacloprid) (thiacloprid), dinotefur (din)
[6] Benzoylurea compounds Chlorfluazuron, bistrifluron, diflubenzuron, flufenoxuron, hexafluuron, fluflutriuron, fluflutriuron etc;
[7] Phenylpyrazole compounds fipronil, pyriprole, pyrafluprole, etc .;
[8] Hydrazine-based compounds Chromafenozide, halofenozide, methoxyphenozide and the like;
[9] Natural insecticide machine oil, nicotine sulfate (nicotine-sulfate);
[10] Other insecticides avermectin (vermectin-B), buprofezin, chlorphenapyr, hydroprene, metoprene, toxacarbine, toxacarbine milbemycin-A), pyridalyl, pyriproxyfen, spinosad, sulfuramid, tolfenpyrad, flubendiamide bromide, flubendiamide Examples include chill (Methyl bromide), potassium oleate (Potassium oleate), and the like.

The active ingredient of the repellent includes, for example, 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.

As an active ingredient of a synergist, for example, 5- [2- (2-butoxyethoxy) ethoxymethyl] -6-propyl-1,3-benzodioxole, 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 for which the heat transpiration agent of the present invention is effective include squids such as Culex mosquitoes and Culex pipiens mosquitoes, aedes such as Aedes aegypti and Aedes albopictus, anopheles such as Aedes albopictus and chironomids.

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 for applying the mosquito control agent of the present invention include a method of volatilizing an 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, 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, the 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 plane. ˜100 mg / m ² . Mosquito coils, mosquito coils, etc. are applied by volatilizing the active ingredient by heating 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 can also be applied in open outdoor spaces.

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

First, the manufacture example of this invention compound is 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 acid To a chloroform solution (5 mL) of acid (124 mg, 0.74 mmol), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (141 mg, 0.74 mmol) and 4-dimethylaminopyridine (5 mg) were added. . After stirring at room temperature for an hour, water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 5]

4-ethynyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate represented by formula (hereinafter referred to as the present invention) 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
To a tetrahydrofuran solution (2 mL) of 4-ethynyl-2,3,5,6-tetrafluorobenzyl alcohol (55 mg, 0.27 mmol), pyridine (106 mg, 1.35 mmol), (1R) -trans-3- (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 poured into the reaction solution, which was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the following formula [Chem. 6]

4-ethynyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2,2-dichloro-1-ethenyl) -2,2-dimethylcyclopropanecarboxylate (hereinafter, This is referred to as the present 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
The present compound A and B 0.3 g and BHT 0.5 g were uniformly stirred and mixed with 99.2 g of a base material for mosquito coils (mixed with insecticide chrysanthemum extract powder, wood powder, tab powder, and starch) 100 mL of water containing malachite green is added as a colorant, and the resulting mixture is molded and dried to obtain a mosquito coil.

Formulation Example 2
Deodorized kerosene is added to and dissolved in 0.8 g of each of the compounds A and B of the present invention, 0.4 g of piperonyl butoxide, and the dye to make a total of 10 mL. 0.5 ml of this solution is impregnated uniformly into a substrate for mosquito mats with a thickness of 22 mm x 35 mm and a thickness of 2.8 mm (a mixture of cotton linter and pulp mixed in a plate shape) Get.

Formulation Example 3
A solution obtained by dissolving 0.7 parts of each of the present compounds A and B and 0.3 part of BHT in 50 parts of a surfactant (diethylene glycol monobutyl ether) and 49 parts of purified water is placed in a polyester container, and the upper part is By inserting a liquid absorbent core (calcined inorganic powder) that can be heated by a heater, an aqueous mosquito repellent liquid agent used in a heat transpiration apparatus is obtained.

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 4 cm × 4 cm, 1.2 cm thick porous ceramic plate to obtain a heated smoke.

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

Effect test example 1 (basic insecticidal activity test against Culex pipiens)
To a petri dish having a diameter of 28 mm, an inner height of 13 mm, and a bottom area of 6.15 cm ² , 0.05 mL of a 0.2% acetone solution containing 0.1 mg of the compound of the present invention [Chemical 5] is added dropwise so that the bottom surface becomes uniform. After spreading, acetone is removed with a double ball. Put 3 female squids in a petri dish with each sample held on the bottom, cover the upper side with a perforated film, record the number of knockdowns every minute, KT ₅₀ (time to knock down 50%) The mortality after 24 hours was measured and recorded. For samples showing a predetermined value or more with respect to the knockdown rate, acetone is further added to the 0.2% acetone solution to dilute it 10-fold to obtain a 0.02% acetone solution. The method was repeated sequentially.
Further, as a comparative control, the following formula [Chemical Formula 7]
4-acetoxymethyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylate 64-66146, hereinafter referred to as Comparative Compound C), and the following formula [Chemical Formula 8]
4-ethynyl-2,3,5,6-tetrafluorobenzyl (1R) -trans-3- (2-fluoro-1-ethenyl) -2,2-dimethylcyclopropanecarboxylate (Japanese Patent Laid-Open No. 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) Tests were similarly conducted 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 is found that the present compound A and the present compound B show a high knockdown effect and a lethal effect on mosquitoes as compared with the comparative compound C, the comparative compound D and the comparative compound E (alleslin). It was.

Effect test example 2 (insecticidal activity test with mosquito coils)
About 100 Aedes aegypti mosquitoes are released in a 3 m cubic small room, and ignited at both ends of 0.1 g of the mosquito coil of the compound A of the present invention and the compound B of the present invention obtained in Formulation Example 1 are placed. The number of knockdowns was recorded every minute and KT ₅₀ (time to knock down 50%) was measured and recorded.
Moreover, the test was similarly performed using the comparison compound C, the comparison compound D, and the comparison compound E (aresulin) as a comparison control.
The results are shown in Table 2.

As a result of the test, the mosquito coil that contains the present compound A and the present compound B as the active ingredient has a higher knock than the comparative compound C, the comparative compound D, and the comparative compound E (aresulin). It was found to show a down effect.

Effect test example 3 (insecticidal activity test against German cockroaches)
An oil agent (neothiozole) having a predetermined concentration (see Table 3) of the present compound A, comparative compound C and comparative compound D was prepared. Ten male German cockroaches were placed in a glass container, covered with a wire mesh, and placed on the bottom of a cylindrical glass container having a diameter of 40 cm and a height of 45 cm. 0.3 ml of the oil was sprayed from a small hole above the glass cylindrical container with a spray gun (pressure 1.5 × 10 ⁶ Pa). Record the number of knockdown over time of up to 10 minutes after was measured KT 50 _(50% knock time to down) 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 comparative compound D against German cockroaches.

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

Claims (6)

[Formula 1]
[Wherein, R represents a methyl group or a chlorine atom. ] The heat transpiration agent for mosquito control which contains the ester compound shown by this as an active ingredient. The heat transpiration agent for mosquito control which contains the ester compound in which R is a methyl group in Claim 1 as an active ingredient. The heat transpiration agent for mosquito control which contains the ester compound whose R is a chlorine atom in Claim 1 as an active ingredient. A mosquito control method using a heat transpiration agent for controlling mosquitoes contained as an active ingredient of the ester compound according to claim 1. A mosquito coil that contains the ester compound according to claim 1 as an active ingredient. The mosquito control method using the mosquito coil which contains the ester compound of Claim 1 thru | or 3 as an active ingredient.