JPH09316035A - Ester compound and noxious like controlling agent containing the compound as active component - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound expressed by a specific formula, exhibiting excellent noxious life controlling effect and useful as a controlling agent. SOLUTION: This compound is expressed by formula I (R is a 1-5C alkyl, a 2-5C alkenyl or a 52-5C alkynyl), e.g. (E)-(RS)-4-methyl-4-octen-1-yn-3-yl (Z)-(1 RS)-cis-2,2-dimenthyl-3-(2-chloro-2-trifluoromethyl)cyclopropanecarbox ylate. The compound can be produced e.g. by reacting a carboxylic acid compound of formula II or its reactive derivative with an alcohol compound of formula III in the presence of a dehydration agent such as dicyclohexylcarbodiimide in an organic solvent such as chloroform at 0-30 deg.C.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to an ester compound and a pest control agent containing the same as an active ingredient.

BACKGROUND OF THE INVENTION Conventionally, for example, Japanese Patent Publication No. 55-42045 discloses that some ester compounds are used as active ingredients such as insecticides. However, it cannot be said that the compound is always always sufficient as an active ingredient such as an insecticide in terms of insecticidal efficacy.

Under the circumstances, the present inventors have conducted diligent studies to find a compound having an excellent pest control effect, and as a result, the ester compound represented by the following general formula The present invention was completed by finding out that it has an excellent pest control effect. That is, the present invention has the general formula

Embedded image [In the formula, R represents a C _{1 to} C ₅ alkyl group (eg, methyl group, ethyl group, isopropyl group, etc.), C _{2 to} C ₅ alkenyl group (eg, allyl group, 3-butenyl group, etc.) or C
_{2 ~C 5} alkynyl group (for example propargyl group ,, 3
Butynyl group). ] The ester compound (Hereinafter, it is described as this invention compound.) Shown by these, and the pest controlling agent which uses it as an active ingredient are provided.

[0002]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention includes stereoisomers (R / S) and geometrical isomers (E / Z), but all stereoisomers having pest control activity are included in the present invention. ,
Geometric isomers and mixtures thereof are included. The compound of the present invention can be produced, for example, by the following method. Formula 3

Embedded image A carboxylic acid compound represented by

Embedded image [Wherein, R represents the same meaning as described above. A method of reacting with an alcohol compound represented by the formula: Examples of the reactive derivative of the carboxylic acid compound of formula 3 include acid halides, preferably acid chlorides.
The amount ratio of the raw materials used is 1 mol of the carboxylic acid compound represented by Formula 3 or its reactive derivative,
The alcohol compound represented by Chemical formula 4 is usually 0.5 to 2 mol. When the carboxylic acid compound itself represented by the formula (3) is reacted with the alcohol compound represented by the general formula (4), the reaction is usually dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethylaminopropyl). It is usually carried out in the presence of a dehydrating agent such as carbodiimide hydrochloride (WSC) in an organic solvent such as chloroform, dichloromethane, tetrahydrofuran (THF), benzene and toluene. The amount of the dehydrating agent used is usually 1 to 5 mol per 1 mol of the carboxylic acid compound represented by Formula 3 or its reactive derivative. An organic base such as pyridine, triethylamine, 4-dimethylaminopyridine or diisopropylethylamine can be coexistent in the reaction. The reaction temperature is usually in the range of -10 ° C to + 100 ° C or the boiling point of the organic solvent used, preferably 0 ° C to 30 ° C. The reaction of the carboxylic acid compound of the carboxylic acid compound represented by the formula (3) with the alcohol compound represented by the general formula (4) is usually carried out with dichloromethane, tetrahydrofuran (T
In an organic solvent such as HF), benzene or toluene,
It is carried out in the presence of a base such as pyridine, triethylamine and 4-dimethylaminopyridine. The amount of base used is represented by formula 3
A carboxylic acid compound represented by or its reactive derivative 1
The amount is usually 1 to 5 mol per mol. The reaction temperature is usually in the range of -10 ° C to + 100 ° C or the boiling point of the organic solvent used, preferably 0 ° C to + 30 ° C. The reaction solution after completion of the reaction can be subjected to usual post-treatments such as extraction with an organic solvent, washing and concentration to isolate the desired compound of the present invention. If necessary, it may be further purified by a usual operation such as chromatography.

The carboxylic acid compound represented by the formula (3), which is one of the intermediates in the production of the compound of the present invention, is prepared according to the method described in Bull. Chem. Soc. Jpn 4385-4394 (1987). Can be manufactured. The other intermediate in the production of the compound of the present invention is represented by the general formula:
The alcohol compound shown by can be produced, for example, by the method shown in the following scheme.

Embedded image Next, steps (i) to (iii) will be described. (i) The step (i) of obtaining an aldehyde compound represented by the formula [I] from 2-methyl-1,3-butadiene is
Giancarlo Eletti-Bianchi, J. Org. Chem, 1648 (1976)
It can be manufactured according to the method described in. (ii) a compound of formula [I]
The step (ii) of obtaining the compound represented by I] will be described. Usually, ethynyl magnesium bromide and an aldehyde compound of formula [I] are reacted in an ether solvent such as tetrahydrofuran. The molar ratio of the raw materials to be subjected to the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar ratio or a ratio close thereto. Reaction temperature is usually −
It can range from 78 ° C. to room temperature. After completion of the reaction, the reaction solution is subjected to usual treatments such as organic solvent extraction and concentration,
The compound of interest can be isolated. If necessary, it can be further purified by an operation such as chromatography. (iii) The step (iii) of obtaining the compound represented by the general formula 4 from the compound represented by the formula [II] will be described. A compound represented by the formula [II] and RMgX [wherein R represents the same meaning as described above, and X represents a chlorine atom, a bromine atom or an iodine atom. ] The Grignard reactant represented by the above formula is usually reacted in an ether solvent such as tetrahydrofuran. The Grignard reagent used in the reaction has the formula [I
It is preferable to use 2 equivalents or more based on the compound represented by the formula [I]. Further, a catalyst such as cuprous chloride may be added in a ratio of, for example, 0.01 to 10 mol with respect to 1 mol of the Grignard reactant. The reaction temperature can usually range from -78 ° C to room temperature. After completion of the reaction, the reaction solution can be subjected to usual treatments such as extraction with an organic solvent and concentration to isolate the desired compound. If necessary, it can be further purified by an operation such as chromatography.

Examples of pests for which the compound of the present invention exerts a controlling effect include the following. Hemiptera Pests Planthoppers such as the brown leafhopper, the brown planthopper, and the white-backed planthopper, leafhoppers such as leafhoppers, green leafhoppers, leafhoppers, leafhoppers, stink bugs, whitefly bugs, insect insects, scale bugs ), Koga noimaiga, Nogameka moth, etc., Japanese common moth, Spodoptera litura, Spodoptera litura, Spodoptera litura, etc.
Hamoguriga acids, tussock acids, Uwaba acids, Kaburayaga, Agurotisu genus such as black cutworm (Agrothis spp.), Heliothis spp (Heliothis spp.), Plutella xylostella, clothes moth, webbing clothes moth, etc. SoShome pest mosquito, Culex such as Culex, Aedes aegypti, Aedes mosquitoes such as Aedes albopictus, Anopheles mosquitoes such as Aedes albopictus, Chironomid species, house flies, house flies, house flies such as house flies, blow flies, flesh flies, seed flies, onion flies, fruit flies, fruit flies, fruit flies, fruit flies and fruit flies Coleoptera pests such as western flies, gnats, flies, corn rootworms such as western corn rootworms and southern corn rootworms, scarab beetles such as staghorn buoy buoys, scarab beetles, weevils such as weevil and rice weevil, white rice worms Shidamashi, mealworm such as red flour beetle, Kisujinomihamushi, Chrysomelidae such as corn rootworm, beetles such, Epilachna genera such as the beetle, Epilachna vigintioctopunctata (Epilachna sp
p.), flat beetle, long-tailed beetle, long-horned beetle, long-horned beetle, blue-footed stag beetle, etc.

Pests of the Lepidoptera, German cockroaches, Black cockroaches, American cockroaches, Black cockroaches, Cockroaches, etc. Orthoptera pests Kera, grasshoppers, etc. Conyptera pests Human fleas, etc. Liceidae pests Human lice, lice, etc. House dust mites, house dust mites, harmful mites such as mites, dust mites, tick mites, and house dust mites

When the compound of the present invention is used as an active ingredient of a pest control agent, it is usually mixed with a solid carrier, a liquid carrier, a gaseous carrier, a bait, or impregnated with a substrate such as mosquito coil or mat. If necessary, add surfactants and other auxiliaries for formulation to prepare oils, emulsions, wettable powders, flowable agents such as water suspensions / emulsions, granules, powders, aerosols, mosquito repellents. Heating and vaporizing agents such as incense sticks, electric mosquito mats, and no mats (liquid electric mosquito coils: liquid-wicking heating transpiration device for insecticide)
Self-combustion type smoke agent / chemical reaction type smoke agent, heated smoke agent such as porous ceramic plate smoke agent, non-heat agent such as resin vaporizer / impregnated paper vaporizer, fuming agent such as fogging agent, ULV agent ,
It is used by formulating it in poison baits. In these formulations, the compound of the present invention is usually added as an active ingredient in a weight ratio of 0.001 to 95.
%contains. Examples of solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (sericite, quartz, Fine powder or granules of sulfur, activated carbon, calcium carbonate, hydrated silica, etc., chemical fertilizers (ammonium sulphate, ammonium phosphide, ammonium nitrate, urea, ammonium salt, etc.) and the like, and examples of liquid carriers include water and alcohol. Kinds (methanol,
Ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methyl naphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (Ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.),
Acid amides (N, N-dimethylformamide, N, N-
Dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, soybean oil, vegetable oil such as cottonseed oil, and the like, and examples of the gaseous carrier, that is, propellant include freon gas and butane gas. , LPG (liquefied petroleum gas),
Examples include dimethyl ether and carbon dioxide. Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives and the like. can give.

Examples of auxiliary agents for preparations such as sticking agents and dispersants are casein, gelatin, polysaccharides (starch powder, gum arabic, cellulose derivatives, alginate sugars), lignin derivatives, bentonites, sugars, synthetic water-soluble polymers. (Polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), and examples of stabilizers include PAP (isopropyl acid phosphate) and BH.
T (2,6-di-tert-butyl-4-methylphenol), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil , Surfactants, fatty acids or esters thereof, and the like. The base material of the mosquito coil includes, for example, a mixture of a raw plant powder such as wood flour and lees flour and a binder such as tub flour, starch and glutein. Examples of the base material of the electric mosquito collecting mat include those obtained by hardening fibrils of cotton linter or a mixture of cotton linter and pulp in a plate shape. Examples of the base component of the self-burning smoke agent include a combustion exothermic agent such as nitrate, nitrite, guanidine salt, potassium chlorate, nitrocellulose, ethyl cellulose, wood powder, alkali metal salt, alkaline earth metal salt, heavy Chromates, pyrolysis stimulants such as chromates, oxygen supplying agents such as potassium nitrate, combustion-supporting agents such as melamine and wheat starch, extenders such as diatomaceous earth, and binders such as synthetic sizing agents. As the base component of the chemical reaction type smoke agent, for example, an alkali metal sulfide, polysulfide, hydrosulfide, hydrous salt, heat generating agent such as calcium oxide, carbonaceous material, iron carbide, catalyst such as activated clay Agents, organic foaming agents such as azodicarbonamide, benzenesulfonyl hydrazide, dinitrosopentamethylenetetramine, polystyrene, polyurethane, natural fiber pieces,
And fillers such as synthetic fiber pieces. Examples of the base material of the non-heated transpiration agent include thermoplastic resin, filter paper, Japanese paper and the like. Examples of base components of poison baits include bait components such as cereal flour, vegetable oil, sugar, crystalline cellulose, antioxidants such as dibutylhydroxytoluene, nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and pepper powder. Examples include ingesting agents, cheese flavors, onion flavors, and peanut oil attractants. Formulations of flowable agents (suspension in water or emulsion in water) generally range from 1 to
75% compound 0.5 to 15% dispersant, 0.1 to 10%
Suspension aid (eg, protective colloid or compound imparting thixotropy), 0 to 10% of suitable auxiliary agent (eg, defoaming agent, rust preventive, stabilizer, spreading agent, penetration aid) , Antifreeze agents, antibacterial agents, antifungal agents, etc.) and finely dispersed in water. It is also possible to use an oil in which the compound hardly dissolves in place of water and use it as a suspension in oil. As the protective colloid, for example, gelatin, casein, gums, cellulose ester, polyvinyl alcohol and the like are used. Examples of the compound imparting thixotropic properties include bentonite, aluminum magnesium silicate, xanthan gum, polyacrylic acid and the like.

The thus obtained preparation is used as it is or diluted with water or the like. Also other pesticides,
It can be used simultaneously with or without mixing with acaricide, nematicide, soil pest control agent, fungicide, herbicide, plant growth regulator, synergist, fertilizer and soil conditioner. Other insecticides and acaricides used include, for example, fenitrothion [O, O-dimethyl O- (3-methyl-4-
Nitrophenyl) phosphorothioate], fenthion [O, O-dimethyl O- (3-methyl-4- (methylthio) phenyl) phosphorothioate], diazinone [O, O-diethyl-O-2-isopropyl-6-methylpyrimidine-4. -Ylphosphorothioate], chlorpyrifos [O, O-diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate], DDVP [2,2
-Dichlorovinyl dimethyl phosphate] and other organic phosphorus compounds, BPMC [2-sec-butylphenylmethylcarbamate], propoxur [2-isopropoxyphenyl N-methylcarbamate] and other carbamate compounds,

Etofenprox [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS) -α-
Cyano-3-phenoxybenzyl (RS) -2- (4-
Chlorophenyl) -3-methylbutyrate], esfenvalerate [(S) -α-cyano-3-phenoxybenzyl (S) -2- (4-chlorophenyl) -3-methylbutyrate], fenpropatrin [( RS) -α-
Cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], cypermethrin [(RS) -α-cyano-3-phenoxybenzyl
(1RS-cis, trans) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1R
S-cis, trans) -3- (2,2-dichlorovinyl)
-2,2-dimethylcyclopropanecarboxylate],
Deltamethrin [(S) -α-cyano-3-phenoxybenzyl (1R-cis) -3- (2,2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate], 2-methyl-2- (4 -Bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) ether, tralomethrin [(1R-cis) 3 [(1'RS)
(1 ', 2', 2 ', 2'-Tetrabromoethyl)]-2,2-dimethylcyclopropanecarboxylic acid (S) -α-cyano-
3-phenoxybenzyl ester], silafluofene [4-ethoxyphenyl {3- (4-fluoro-3-phenoxyphenyl) propyl} dimethylsilane], d-
Phenothrin [3-phenoxybenzyl (1R-cis, trans) -chrysanthemate], cyphenothrin [(RS) -α-cyano-3-phenoxybenzyl
(1R-cis, trans) -chrysanthemate], d-
Resmethrin [5-benzyl-3-furylmethyl (1R
-Cis, trans) -chrysanthemate], acrinasulin [(S) -α-cyano-3-phenoxybenzyl
(1R-cis (Z))-(2,2-dimethyl-3- {3-
Oxo-3- (1,1,1,3,3,3-hexafluoropropyloxy) propenyl} cyclopropanecarboxylate], cyfluthrin [(RS) -α-cyano-4-fluoro-3-phenoxybenzyl 3- (2,2-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], lambdahalothrin [(RS) -α-cyano-3]
-Phenoxybenzyl (1RS-cis (Z))-3-
(2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], tefluthrin [2,3,5,6-tetrafluoro-4-]
Methylbenzyl (1RS-cis (Z))-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,
2-dimethylcyclopropanecarboxylate], transfluthrin [2,3,5,6-tetrafluorobenzyl (1R-trans) -3- (2,2-dichlorovinyl)-
2,2-Dimethylcyclopropanecarboxylate], Praresulin [(S) -2-methyl-4-oxo-3-]
(2-propynyl) -2-cyclopenten-1-yl
(1R-cis, trans) -Chrysanthemate, d-allethrin [2-methyl-4-oxo-3- (2-propenyl) -2-cyclopenten-1-yl (1R-cis, trans) -closanthemate , D-tetramethrin [3,4,5,6-tetraphthalimidomethyl (1R-cis, trans) -chrysanthemate and other pyrethroid compounds,

Imidacloprid [1- (6-chloro-3
-Pyridylmethyl) -N-nitroimidazolidine-2-
Nitro imidazolidine derivatives such as ylidene amine], chlorfluazuron [1- (3,5-dichloro-4- (3-
Chloro-5-trifluoromethylpyridin-2-yloxy) phenyl) -3- (2,6-difluorobenzoyl) urea], teflubenzuron [1- (3,5-dichloro-2,4-difluorophenyl) -3- (2,6-Difluorobenzoyl) urea], Flufenoxuron [1-
(4- (2-chloro-4-trifluoromethylphenoxy) -2-fluorophenyl] -3- (2,6-difluorobenzoyl) urea], diflubenzuron [1- (4
-Chlorophenyl) -3- (2,6-difluorobenzoyl) urea] and the like, benzoylphenylurea-based compounds, phenylpyrazole-based compounds, methoxadiazone [5-methoxy-3- (2-methoxyphenyl) -1,
3,4-oxadiazol-2 (3H) -one] and the like.

When the compound of the present invention is used as an active ingredient of an agricultural pest control agent, its application amount is usually 0.1 to 500 g per 10 ares, and an emulsion, a wettable powder, a flowable agent, etc. are diluted with water. When applied, the application concentration is 0.1-
It is 1000ppm, and granules, powders, etc. are applied as it is without any dilution. When it is used as an active ingredient of a pest control agent for household and epidemic prevention, emulsions, wettable powders, flowable agents, etc. are diluted with water to 0.1 to 10,000 ppm and applied, and oil, aerosol, fumigant, and smoke are applied. For agents, evaporants, fumes, ULV, poison baits, etc., apply as they are.
These application rates and application concentrations differ depending on the type of preparation, application time, application place, application method, type of pest, degree of damage, etc., and may be increased or decreased without being affected by the above range. can do.

[0012]

EXAMPLES The present invention will be described in more detail with reference to production examples, formulation examples, test examples, etc., 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 (E)-(RS) -3-hydroxy-4-methyl-4-
Octene-1,7-diyne 300 mg, 2,6-di-tert
-Butyl-4-methylphenol 5 mg, pyridine 226
mg, 4-dimethylaminopyridine 5 mg and toluene 1
To a mixed solution of 0 ml, under ice cooling, (Z)-(1RS) -cis-2,2-dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropenecarboxylic acid chloride 525
mg was added dropwise and the reaction was continued at room temperature for 6 hours. Then, the reaction solution was poured into ice-cooled 5% citric acid, extracted three times with diethyl ether, the ether layers were combined, washed successively with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. Distilled off. The residue was subjected to silica gel column chromatography (developing solvent: n-hexane / ethyl acetate mixture (30:
1)), and (E)-(RS) -4-methyl-4-octen-1,7-diin-3-yl (Z)-(1R
S) -cis-2,2-dimethyl-3- (2-chloro-2
-Trifluoromethyl) cyclopropanecarboxylate (the present compound (7)) (yield 41%) was obtained.
n _D ²¹ 1.4748 Production Example 2 (E) - (RS) -3- hydroxy-4-methyl-3,
8-Octadiene-1-yne 300 mg, 2,6-di-te
rt-Butyl-4-methylphenol 5 mg, pyridine 20
(Z)-(1RS) -cis-2,2-dimethyl-3- (2-chloro-2-trifluoromethyl) cyclohexyl was added to a mixed solution of 2 mg, 4-dimethylaminopyridine 5 mg and toluene 10 ml under ice cooling. Propanecarboxylic acid chloride 47
0 mg was added dropwise and the reaction was continued at room temperature for 6 hours. Then, the reaction solution was poured into ice-cooled 5% citric acid water and extracted three times with diethyl ether. The ether layers were combined, washed successively with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent: hexane / ethyl acetate mixture (3
0: 1)) and (E)-(RS) -4-methyl-
3,8-Octadien-1-in-3-yl (Z)-
(1RS) -cis-2,2-dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylate (the present compound (3)) (88% yield) was obtained. n _D ²³ 1.4685 Production Example 3 (E) - (RS) -3- hydroxy-4-methyl-4-
Hepten-1-yne 1500 mg, 2,6-di-tert-butyl-4-methylphenol 10 mg, pyridine 202 mg, 4
-Dimethylaminopyridine 10 mg and toluene 50 ml
(Z)-(1RS) -cis-
3090 mg of 2,2-dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylic acid chloride was added dropwise, and the reaction was continued at room temperature for 6 hours. Then, the reaction solution was poured into ice-cooled 5% citric acid water and extracted three times with diethyl ether. The ether layers were combined, washed successively with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent: hexane / ethyl acetate mixture (30:
1)), (E)-(RS) -4-methyl-4-hepten-1-yn-3-yl (Z)-(1RS) -cis-2,2-dimethyl-3- (2 3280 mg (yield 78%) of -chloro-2-trifluoromethyl) cyclopropanecarboxylate (the present compound (5)) was obtained.
n _D ²⁵ 1.4609

Examples of the compounds of the present invention are shown below together with the compound numbers. (1) (E)-(RS) -4-methyl-4-octene-1
-In-3-yl (Z)-(1RS) -cis-2,2
-Dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylate (2) (E)-(RS) -4,6-dimethyl-4-hepten-1-yn-3-yl (Z )-(1RS) -cis-
2,2-Dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylate (3) (E)-(RS) -4-methyl-3,8-octadiene-1-yne-3- Il (Z)-(1RS) -cis-2,2-dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylate
(N _D ²³ 1.4685) (4) (E)-(RS) -4-methyl-4-nonene-1,
8-diin-3-yl (Z)-(1RS) -cis-2,
2-Dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylate (5) (E)-(RS) -4-methyl-4-heptene-1
-In-3-yl (Z)-(1RS) -cis-2,2
-Dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylate
(N _D ²⁵ 1.4609) (6) (E)-(RS) -4-methyl-3,7-heptadien-1-yn-3-yl (Z)-(1RS) -cis-2,2-dimethyl- 3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylate
(N _D ²⁴ 1.4651) (7) (E)-(RS) -4-methyl-4-octene-
1,7-diin-3-yl (Z)-(1RS) -cis-
2,2-Dimethyl-3- (2-chloro-2-trifluoromethyl) cyclopropanecarboxylate
(N _D ²¹ 1.4748)

Next, formulation examples are shown. The parts are parts by weight, and the compounds of the present invention are represented by the above compound numbers. Formulation Example 1 Emulsion 20 parts of each of Compounds (1) to (7) was dissolved in 65 parts of xylene, 15 parts of emulsifier Sorpol 3005X (registered trademark of Toho Kagaku) was added, and the mixture was thoroughly mixed with stirring to prepare a 20% emulsion of each. To get Formulation Example 2 Wettable powder 40 parts of each of the compounds (1) to (7) and Solpol 3005X
Add 5 parts (above), mix well, and use Carplex #
32 parts of 80 (Shionogi registered trademark, synthetic silicon oxide hydroxide fine powder) and 23 parts of 300 mesh diatomaceous earth are added and mixed by stirring with a juice mixer to obtain each 40% wettable powder. Formulation Example 3 Granules 1.5 parts each of Compounds (1) to (7) and AGSORBLVM-MS
24/48 (fired montmorillonite manufactured by OIL DRI,
98.5 parts of granular carrier having a particle size of 24 to 48 mesh) and well mixed to obtain each 1.5% granule. Formulation Example 4 Microcapsules After mixing 10 parts of each of the compounds (1) to (7), 10 parts of phenylxylylethane and 0.5 part of Sumidule L-75 (tolylene diisocyanate manufactured by Sumitomo Bayer Urethane Co.), Add to 20 parts of 10% aqueous solution of gum arabic and stir with a homomixer to obtain an emulsion having an average particle size of 20 μm. Next, 2 parts of ethylene glycol was added thereto, and the mixture was further reacted in a warm bath at 60 ° C. for 24 hours to obtain a microcapsule chiller. On the other hand, Zangsangam 0.
2 parts and 1.0 part of Veegum R (aluminum magnesium silicate manufactured by Sanyo Kasei) are dispersed in 56.3 parts of ion-exchanged water to obtain a thickener solution. 42.5 parts of the above microcapsule chiller and 57.5 parts of thickener solution are mixed to obtain each 10% microcapsule. Formulation Example 5 Flowable Agent After mixing 10 parts of each of the compounds (1) to (7) and 10 parts of phenylxylylethane, the mixture was added to 20 parts of a 10% aqueous solution of polyethylene glycol and stirred with a homomixer to give average particles. An emulsion with a diameter of 3 μm is obtained. On the other hand, 0.2 parts of zansan gum and 1.0 part of veegum R (aluminum magnesium silicate manufactured by Sanyo Kasei) were added to 58.8 of deionized water.
To obtain a thickener solution. Emulsion 4 above
0 parts and 60 parts thickener solution are mixed to obtain 10% of each
Get a flowable agent. Formulation Example 6 Powder 5 parts of each of Compounds (1) to (7) was added to Carplex # 8.
3 parts of 0 (the above), PAP of 0.3 and 91.7 parts of 300-mesh talc are added and mixed by stirring with a juice mixer to obtain each 5% powder.

Formulation Example 7 Oil agent 0.1 parts of each of the compounds (1) to (7) was added to dichloromethane 5
Parts and mixed with 94.9 parts of deodorized kerosene to give each 0.1% oil. Formulation Example 8 Oily aerosol 1 part of each of the compounds (1) to (7), 5 parts of dichloromethane and 34 parts of deodorant kerosene are mixed and dissolved, filled into an aerosol container, and a valve part is attached, and then a propellant is passed through the valve part. 60 parts of (liquefied petroleum gas) is charged under pressure to obtain each oil-based aerosol. Formulation Example 9 Aqueous aerosol Compounds (1) to (7) of 0.6 parts each, 5 parts of xylene, 3.4 parts of deodorizing kerosene and 1 part of an emulsifier {Atmos 300 (registered trademark of Atlas Chemical Co.)} were mixed and dissolved. things and,
50 parts of pure water is filled in an aerosol container, a valve portion is attached, and 40 parts of a propellant (liquefied petroleum gas) is filled under pressure through the valve portion to obtain each aqueous aerosol. Formulation Example 10 Mosquito coil Incense 0.3 g of each of the compounds (1) to (7) was dissolved in 20 ml of acetone, and a carrier for mosquito coil (tub powder: lees powder: wood powder 4:
After mixing with 99.7 g of the mixture uniformly in a ratio of 3: 3), 120 ml of water was added, and the mixture was thoroughly kneaded and dried to obtain each mosquito coil. Formulation Example 11 Electric Mosquito Repellent Mat Acetone was added to 0.8 g of each of Compounds (1) to (7) and 0.4 g of piperonyl butoxide to dissolve them, and a total of 1
Make up to 0 ml. 0.5 ml of this solution is 2.5 cm × 1.5 cm, and the thickness is 0.5.
Each of the electric mosquito repellent mats is obtained by uniformly impregnating into a 3 cm base material for electric mat (a fibril of a mixture of cotton linter and pulp is hardened into a plate shape). Formulation Example 12 Liquid Electric Mosquito Repellent Liquid Absorbent core (inorganic powder) in which 3 parts of each of Compounds (1) to (7) was dissolved in 97 parts of deodorized kerosene, placed in a vinyl chloride container, and the upper part of which could be heated by a heater. Each of the liquid electric mosquito repellents is obtained by solidifying with a binder and sintering. Formulation Example 13 Heating Smoke Agent Compounds (1) to (7) (100 mg) are each dissolved in an appropriate amount of acetone and impregnated into a 4.0 cm × 4.0 cm, 1.2 cm thick porous ceramic plate, Get a heated smoker. Formulation Example 14 Room temperature volatilizer 100 μg of each of the compounds (1) to (7) is dissolved in an appropriate amount of acetone, and uniformly applied on a filter paper of 2 cm × 2 cm and a thickness of 0.3 mm, and then air-dried with acetone, respectively. To obtain a room temperature transpiration agent. Formulation Example 15 Mite-proof sheet Acetone solution of each of the compounds (1) to (7) was dissolved in 1 on filter paper.
Impregnation is performed so that the amount becomes 1 g per m ² , and acetone is air-dried to obtain each mite-proof sheet.

Next, it will be shown by test examples that the compound of the present invention is useful as an active ingredient of a pest controlling agent. The compounds of the present invention have the above-mentioned compound numbers, and the compounds used for comparison and control are shown by the compound symbols in Table 1.

[Table 1] Test Example 1 Insecticidal test by volatilization at room temperature against houseflies 0.007% of the test compound was placed on an aluminum dish with a diameter of 7 cm at the bottom.
0.64 ml of a 4% acetone diluted solution was added dropwise and the acetone was air dried. Polyethylene cup (diameter 9 cm, height 4.5
(10 cm) of 10 female adult house flies of the CSMA type were released in a cm), and a 16-mesh nylon net was placed on the upper part of the adult to prevent the insects from directly touching the drug-treated surface. The cup was turned upside down and placed on the above aluminum dish, and after 60 minutes at 25 ° C., Agony worms were counted and the Agony worm rate was calculated. As a result, each of the compounds (5), (6) and (7) of the present invention showed an agony rate of 100%. In contrast, the comparative compound (A) has an anguish rate of 10
%showed that.

Claims (2)

[Claims] 1. A general formula: ## STR1 ##[In the formula, R is C₁~ C_FiveAlkyl group, C_Two~ C_FiveAl
Kenyl group or C_Two~ C _FiveRepresents an alkynyl group. ]]
Ester compound. 2. A pest control agent comprising the ester compound according to claim 1 as an active ingredient.