JP2000044516A - Pyrethroid compound and pest-controlling agent by using the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a pyrethroid compound which is a specific stereoisomer of a compound having insecticidal activities, capable of manifesting excellent pest-controlling activities and safety to a mammal, and useful as an active ingredient for a pest-controlling agent. SOLUTION: This pyrethroid compound is (S)-2-methyl-4-oxo-3-(2-propynyl)- cyclopent-2-enyl (1R)-trans-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate compound. The compound is obtained, for example, by reacting (S)-2-methyl-4-oxo-3-(2-propynyl)-cyclopent-2-enylalcohol of formula II with (1R)-trans-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylic acid of formula III or a reactive derivative thereof. When the compound of formula I is used as an active ingredient for a pest-controlling agent, the pest-controlling agent contains preferably 0.001-95 wt.% compound of formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a pyrethroid compound and a pesticidal composition containing the same as an active ingredient.

[0002]

BACKGROUND OF THE INVENTION Conventionally, 2-methyl-4-oxo-3- (2-propynyl)
It is known that 3-dihalovinyl-2,2-dimethylcyclopropanecarboxylic acid esters of -cyclopent-2-enyl alcohol have insecticidal activity (see JP-B-61-57820). However, depending on the use scene, such a pest control agent is not only forced to restrict its use not only in terms of its control effect but also in terms of safety. ,
Usually, since it is mainly used in a limited space in a living environment, it is required to have required insecticidal activity and repellent activity, as well as high safety for mammals such as humans, livestock, and pets. .

[0003]

Under these circumstances, the present inventors have conducted intensive studies and as a result, have found that 2-methyl-4-oxo-3- (2-propynyl) -cyclopent-2-enyl 3- Specific stereoisomers of (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate are excellent in pest control effect and safety to mammals (acute toxicity, sensitization, irritation, etc.) The present invention was found to be a compound of the present invention. That is, the present invention provides

Embedded image (S) -2-methyl-4-oxo-3- (2
-Propynyl) -cyclopent-2-enyl (1R)
-Trans-3- (2,2-dichlorovinyl) -2,2
-Dimethylcyclopropanecarboxylate (hereinafter, referred to as the compound of the present invention); and a pest control agent containing the compound of the present invention as an active ingredient.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION The compound of the present invention is, for example,

Embedded image (S) -2-methyl-4-oxo-3- (2
-Propynyl) -cyclopent-2-enyl alcohol (hereinafter referred to as an alcohol compound) and Formula 4

Embedded image (1R) -trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylic acid (hereinafter referred to as carboxylic acid compound) or a reactive derivative of carboxylic acid compound (for example, (An acid halide, an acid anhydride, etc.).

The reaction is usually carried out in a solvent in the presence of a condensing agent or a base. Examples of the condensing agent include dicyclohexylcarbodiimide (DCC) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (WSC). As the base, for example, triethylamine, pyridine, N,
N-diethylaniline, 4-dimethylaminopyridine,
Organic bases such as diisopropylethylamine are exemplified.

Examples of the solvent include hydrocarbons such as benzene, toluene and hexane, ethers such as diethyl ether and tetrahydrofuran, dichloromethane and 1,1.
And halogenated hydrocarbons such as 2-dichloroethane.

[0007] The reaction time is usually in the range of 5 minutes to 72 hours. The reaction temperature is usually -20 ° C to 100 ° C (however, when the boiling point of the solvent is less than 100 ° C,
(Boiling point of the solvent), preferably -5 ° C to 100 ° C.
° C (however, when the boiling point of the solvent is less than 100 ° C,
C. to the boiling point of the solvent). An alcohol compound;
The molar ratio of use with the carboxylic acid compound or the reactive derivative of the carboxylic acid compound can be arbitrarily set, but it is preferable to use an equimolar ratio or a ratio close thereto. The amount of the condensing agent or base with respect to the alcohol compound can be used in any ratio, and it is preferable to use an equimolar to 5 mol of the condensing agent or base per 1 mol of the alcohol compound.

After completion of the reaction, the compound of the present invention can be obtained by subjecting the reaction mixture to ordinary post-treatment operations such as extraction with an organic solvent and concentration. The compound of the present invention can be further purified by a usual operation such as chromatography, distillation and recrystallization, if necessary.

The alcohol compound is disclosed in, for example,
No. 1151, etc., and the carboxylic acid compound can be produced according to the method described in, for example, JP-A-4-23491.

Examples of pests against which the compound of the present invention can exert a controlling effect include the following. The compounds of the present invention are useful as an active ingredient of a controlling agent for these pests, and are particularly excellent in safety. Therefore, it is particularly useful as an active ingredient of a pest control agent for epidemic control requiring high safety for mammals. Lepidopteran pests: Japanese bats such as Japanese scabbard moth, Kobnomameiga and Noshimekokuga, Spodoptera such as Spodoptera litura, Armyworm, Spodoptera litura, White butterflies such as Monstroca biloba, Crested moths such as Kokakumamonamaki, Singing moths, Scutellaria, Scotch moths Agrotis spp., Helicoverpa spp., Heliotis pests (Helovertis spp.)
iothis spp.), Convolvulus, Scutellaria spp., Iga, Koiga, Noshimekokuga etc. Dipteran pests: Culex mosquitoes such as Culex pipiens, Aedes albopictus, Aedes albopictus, Aedes albopictus such as Aedes albopictus, Anopheles japonicus, Musca domestica House flies such as house flies, blowflies, flies, flies, flies, onions, etc., fruit flies, drosophila, flies, flies, flies, flies, flies, etc. Reticulate pests: German cockroaches, German cockroaches, Water cockroaches, brown cockroaches, German cockroaches, etc. Hymenoptera pests: ants, wasps, wasps,
Pteridophytes such as wasps, etc. Laminariae pests: dog flea, cat flea, human flea, etc. Lice pests: human lice, lice, head lice,
Body lice, etc. Isoptera insects: Yamato termites, house termites, etc. Mites: Dermatophagoides such as Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides farinae such as Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides farinae such as red mite, Scaropteridae and others. Tick mites such as dust mite, maricite mite, house mite, spider mite, Kanzawa spider mite, mandarin spider mite, apple spider mite, etc .; Hemiptera: insects such as brown planthoppers, brown planthoppers and brown planthoppers, leafhoppers such as leafhoppers and leafhoppers, leafhoppers such as aphids, stinkbugs, whiteflies, scale insects, and insects,
Coleoptera, etc .: Coleopteran insects: Corn rootworms, such as brown beetle, brown beetle, western corn rootworm, southern corn rootworm, beetles such as beetle buoy, turf beetle, weevil, rice weevil, weevil, etc. (Epilac) such as Tenebrion beetles (e.g., beetles, beetles, beetles, and beetles), beetles (e.g., beetles, beetles, beetles, and beetles);
hna spp.), Leaf beetle, Long-spotted beetle, Longhorn beetle, Long-tailed beetle, etc. Orthoptera: Thrips palmi, Thrips palmi, Thrips etc. Orthoptera: Kera, Grasshopper

In the present invention, the pesticidal agent is intended particularly for insecticide, miticide and repellent of pests. When the compound of the present invention is used as an active ingredient of a pesticidal agent, usually, a solid carrier, a liquid carrier, a gaseous carrier, a bait bait, a base of a mosquito coil and a compound of the present invention and a solution thereof are mixed, and if necessary, an interface is prepared. Oils, emulsions, wettable powders, suspensions in water, by adding active agents and other pharmaceutical auxiliaries, or by impregnating a base such as mosquito coils and mats with the compound of the present invention or a solution thereof. Flourable agents such as water-in-water emulsions; Granules; Powders; Aerosols; Heat-evaporating agents such as mosquito coils, electric mosquito-cat mats, liquid-absorbent core-type heat-evaporating liquids; Heated smokers such as reactive smokers and perforated ceramic plate smokers; non-heated vaporizers such as resin vaporizers and impregnated paper vaporizers; fogging agents such as fogging; ULV
Agent: Used as a poison bait or the like. These formulations include:
The compound of the present invention as an active ingredient is usually added in a weight ratio of 0.0
It is contained from 01 to 95%.

[0012] Examples of the solid carrier used in the formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasamikure, acid clay, etc.), talcs, ceramics, sericite, quartz. ,
Examples include inorganic carrier such as calcium carbonate, synthetic resin such as polyethylene and polypropylene, fine powder or granular material of plant-derived carrier such as wood flour and activated carbon. Examples of the liquid carrier include water, alcohols (methanol, ethanol, higher alcohols and the like), 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,
Vegetable oils such as dioxane, acid amides (N, N-dimethylformamide, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide, soybean oil, cottonseed oil, etc. And the like. As the liquefied gas carrier, for example, fluorocarbon, fluorohydrocarbon,
LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide and the like.

The surfactant includes, for example, alkyl sulfates, alkyl sulfonates, alkyl allysates.
Sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers
Examples thereof include ters, polyhydric alcohol esters, and sugar alcohol derivatives. Examples of pharmaceutical auxiliaries such as fixatives and dispersants include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers (Polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.). Examples of the stabilizer include BHT (2,6-di-tert-butyl-).
4-methylphenol), BHA (2-tert-butyl-4-methoxyphenol and 3-tert-butyl-
Phenol-based antioxidants such as mixtures with 4-methoxyphenol), amine-based antioxidants such as diphenylamine, organic sulfur-based antioxidants such as 2-mercaptobenzimidazole, PAP (isopropyl isopropyl phosphate), vegetable oil , Mineral oil, surfactants, fatty acids or esters thereof, and the like.

The base material of the mosquito coil includes, for example, wood flour,
Mixtures of a raw plant powder such as cake powder and a binder such as tub powder, starch, glutein and the like can be mentioned. Examples of the base material of the electric mosquito collecting mat include a plate obtained by hardening fibrils of cotton linter or a mixture of cotton linter and pulp. As the base material of the self-burning type smoke agent, for example, nitrate, nitrite, guanidine salt, potassium chlorate, nitrocellulose, ethylcellulose,
Combustion exothermic agents such as wood flour; thermal decomposition stimulants such as alkali metal salts, alkaline earth metal salts, dichromates and chromates; oxygen supply agents such as potassium nitrate; flame retardants such as melamine and wheat starch; Examples include bulking agents such as algae soil, and binders such as synthetic paste.

Examples of the base material of the chemical reaction type smoke agent include exothermic agents such as alkali metal sulfides, polysulfides, hydrosulfides, hydrated salts, calcium oxide, carbonaceous materials, iron carbide, and the like.
Examples include catalysts such as activated clay, organic blowing agents such as azodicarbonamide, benzenesulfonyl hydrazide, dinitrosopentamethylenetetramine, polystyrene, and polyurethane, and fillers such as natural fiber fragments and synthetic fiber fragments. Examples of the base material of the non-heated evaporant include a thermoplastic resin, filter paper, Japanese paper, and the like.

Examples of the bait bait include bait ingredients such as cereal flour, vegetable oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaseletic acid; and preservatives such as dehydroacetic acid. And edible powders such as pepper powder, cheese flavor, onion flavor, peanut oil and the like.

Flowable agents (suspension in water or emulsion in water) are usually compounds of the present invention, dispersants, suspension aids (eg, protective colloids and compounds that impart thixotropy), and suitable auxiliaries. (For example, an antifoaming agent, a rust inhibitor, a stabilizer, a spreading agent, a penetration aid, an antifreezing agent, an antibacterial agent, a fungicide, etc.) and water. Examples of protective colloids include gelatin, casein, gums, cellulose ether, polyvinyl alcohol, and the like. Examples of compounds that impart thixotropic properties include, for example, bentonite and aluminum magnesium silicate. , Xanthan gum, polyacrylic acid and the like.
Also, an oil in which the compound of the present invention hardly dissolves can be used as a suspension in oil instead of water. The preparation obtained in this way, as it is, according to its purpose,
Alternatively, it is used after being diluted with water or the like.

Further, it can be mixed or used in combination with other insecticides, acaricides, repellents, synergists and the like. Examples of such insecticides and acaricides include fenitrothion [O, O-dimethyl O- (3-methyl-4-nitrophenyl) phosphorothioate] and fenthion [O, O
-Dimethyl O- (3-methyl-4- (methylthio) phenyl) phosphorothioate], diazinon [O, O
-Diethyl-O-2-isopropyl-6-methylpyrimidin-4-yl phosphorothioate], chloropyrifos [O, O-diethyl-O-3,5,6-trichloro-2]
-Pyridyl phosphorothioate], acephate [O,
S-dimethylacetyl phosphoramidothioate], methidathion [S-2,3-dihydro-5-methoxy-2-
Oxo-1,3,4-thiadiazol-3-ylmethyl O, O-dimethylphosphorodithioate], disulfotone [O, O-diethyl S-2-ethylthioethylphosphorodithioate], DDVP [2,2-dichlorovinyldimethylphosphate], sulphophos [O-ethyl O-4- (methylthio) phenyl S-propyl phosphorodithioate], cyanophos [O-4-cyanophenyl O, O -Dimethyl phosphorothioate], dioxabenzophos [2-methoxy-4H-1,3,2-benzodioxaphosphorin-2-sulfide], dimethoate [O, O-dimethyl-S- ( N-methylcarbamoylmethyl) dithiophosphate], phentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate], malachi Emissions [diethyl (dimethoxy phosphino Chi oil thio) Sakushine - DOO], trichlorfon [dimethyl 2,2,2-trichloro-1-hydroxyethyl phosphate bone - DOO], azinphos-methyl [S-
3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O, O-dimethylphosphorodithioate], monocrotophos [dimethyl (E) -1
Organic phosphorus compounds such as -methyl-2- (methylcarbamoyl) vinyl phosphate], ethion [O, O, O ', O'-tetraethyl S, S'-methylenebis (phosphorodithioate)], and BPMC (2- sec-butylphenylmethylcarbamate], benfracarb [ethyl
N- [2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl (methyl) aminothio]
-N-isopropyl-β-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-2,2
-Dimethyl-7-benzo [b] furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl-N-methylcarbamate], mesomil [S-methyl-N-[( Methylcarbamoyl) oxy]
Thioacetimidate), ethiophenecarb [2-
(Ethylthiomethyl) phenylmethylcarbamate],
Aldicarb [2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyloxime],
Oxamyl [N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide], phenothiocarb [S-4-phenoxybutyl) -N, N
Carbamate compounds such as dimethylthiocarbamate;

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 (1RS) -cis, trans-3- (2,2-
Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], cyhalothrin [(RS) -α-cyano-3-phenoxybenzyl (Z)-(1RS) -cis-3- (2-chloro-3, 3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S) -α-cyano-3-phenoxybenzyl (1R) -cis-3 (2,
2-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate], cycloprothrin [(RS)-
α-cyano-3-phenoxybenzyl (RS) -2,2
-Dichloro-1- (4-ethoxyphenyl) cyclopropanecarboxylate], fluvalinate (α-cyano-3-phenoxybenzyl N- (2-chloro-α, α,
α-trifluoro-p-tolyl) -D-barynate),
Bifenthrin (2-methylbiphenyl-3-ylmethyl) (Z)-(1RS) -cis-3- (2-chloro-
3,3,3-trifluoroprop-1-enyl) -2,
2-dimethylcyclopropanecarboxylate, 2-methyl-2- (4-bromodifluoromethoxyphenyl)
Propyl (3-phenoxybenzyl) ether, tralomethrin [(1R-cis) 3} (1RS) (1,2,2
2,2-tetrabromoethyl) {-2,2-dimethylcyclopropanecarboxylic acid (S) -α-cyano-3-phenoxybenzyl ester], silafluofen [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], 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], tetramethrin [3,4,5,6-tetrahydro Phthalimidomethyl (1RS) -cis, trans-chrysanthemate],
Allethrin [(RS) -3-allyl-2-methyl-4-
Oxocyclopent-2-enyl (1RS) -cis, trans-chrysanthemate], prarethrin [(S)-
2-methyl-4-oxo-3- (2-propynyl) cyclopent-2-enyl (1R) -cis, trans-chrysanthemate], empentrin [(RS) -1-ethynyl-2-methyl-2-pentenyl (1R) -cis,
Trans-chrysanthemate], imiprothrine [2,
5-dioxo-3- (prop-2-ynyl) imidazolidin-1-ylmethyl (1R) -cis, trans-2,
2-dimethyl-3- (2-methylprop-1-enyl)
Cyclopropane carboxylate], d-framethrin [5- (2-propynyl) furfuryl (1R) -cis,
Trans-chrysanthemate], pyrethroid compounds such as 5- (2-propynyl) furfuryl 2,2,3,3-tetramethylcyclopropanecarboxylate,

N-cyanoamidine derivatives such as nitroimidazolidine derivatives, acetamiprid [N-cyano-N'-methyl-N '-(6-chloro-3-pyridylmethyl) acetamidine], and endosulfan [6,7,8,
9,10,10-hexachloro-1,5,5a, 6
9,9a-Hexahydro-6,9-methano-2,4,3
-Benzodioxathiepine oxide], γ-BHC
(1,2,3,4,5,6-hexachlorocyclohexane), 1,1-bis (chlorophenyl) -2,2,2-
Chlorinated hydrocarbon compounds such as trichloroethanol, chlorofluazurone [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-
Benzoylphenylurea-based compounds such as difluorobenzoyl) urea] and diafenthiuron [N- (2,6
-Diisopropyl-4-phenoxyphenyl) -N'-
thiourea derivatives such as tert-butylcarbodiimide], phenylpyrazole compounds, methoxadiazone [5-methoxy-3- (2-methoxyphenyl) -1,
3,4-oxadiazol-2- (3H) -one], bromopropylate [isopropyl 4,4'-dibromobenzylate], tetradiphone [4-chlorophenyl]
2,4,5-trichlorophenylsulfone], quinomethionate [S, S-6-methylquinoxaline-2,3-
Diyldithiocarbonate), pyridaben [2-ter
t-butyl-5- (4-tert-butylbenzylthio) -4-chloropyridazin-3 (2H) -one], fenpyroximate [tert-butyl (E) -4-
[(1,3-dimethyl-5-phenoxypyrazole-4)
-Yl) methyleneaminooxymethyl] benzoe-
G), debufenpyrad [N-4-tert-butylbenzyl) -4-chloro-3-ethyl-1-methyl-5-
Pyrazole-carboxamide), polynactin complex (tetranactin, dinactin, trinactin),
Pyrimidifen [5-chloro-N- [2- {4- (2-
(Ethoxyethyl) -2,3-dimethylphenoxydiethyl] -6-ethylpyrimidin-4-amine, milbemectin, abamectin, iva-mectin, azadirachtin [AZAD] and the like.
3,4-caranediol, N, N-diethyl-m-toluamide, 1-methylpropyl 2- (2-hydroxyethyl) -1-piperidinecarboxylate, p-menthane-3,8-diol, hyssop oil and the like Vegetable essential oils and the like, and as a synergist, for example, bis- (2,3,
3,3-tetrachloropropyl) ether (S-42
1), N- (2-ethylhexyl) bicyclo [2.2.
1] Hept-5-ene-2,3-dicarboximide (MGK-264), α- [2- (2-butoxyethoxy) ethoxy] -4,5-methylenedioxy-2-propyltoluene (piperonyl butoxide) And the like.

When the compound of the present invention is used as an active ingredient of an insect-controlling agent for household epidemics or animals, an emulsion, a wettable powder,
Formulations such as flowables are usually diluted with water to a concentration of 0.1 to 10000 ppm as the compound of the present invention and applied. Oils, aerosols, fumigants, fumigants, vaporizers, aerosols, U
Formulations such as LV agent, poison bait, and resin formulation are applied as they are. All of these application rates and application concentrations are based on the type of preparation, application time, application place, application method, type of pest,
It can be determined appropriately depending on the situation such as the degree of damage.

[0022]

EXAMPLES The present invention will be described in more detail with reference to Production Examples, Formulation Examples and Test Examples, 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 (S) -2-methyl-4-oxo-3- (2-propynyl) -cyclopent-2-enyl alcohol 5.0 g,
(1R) -trans-3- (2,2-dichlorovinyl)
3.4 g of pyridine was added to a mixed solution of 8.0 g of -2,2-dimethylcyclopropanecarboxylic acid chloride and 50 ml of toluene under ice cooling, and the reaction was continued at room temperature for 12 hours. Thereafter, about 5 aqueous saturated ammonium chloride was added to the reaction mixture.
0 ml, and the mixture was added with 50 ml of diethyl ether.
Extracted times. The diethyl ether layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography, and then recrystallized with a mixed solvent of hexane and ethyl acetate, and ( S) -2-Methyl-4-oxo-3- (2-
Propynyl) -cyclopent-2-enyl (1R)-
Trans-3- (2,2-dichlorovinyl) -2,2-
8.9 g of dimethylcyclopropanecarboxylate were obtained (78% yield). This compound was not sensitizing or irritating to the skin. ¹ H-NMR (CDCl ₃ , TMS internal standard) δ value (pp
m): 1.21 (s, 3H), 1.29 (s, 3H), 1.64
(d, 1H), 2.00 (t, 1H), 2.18 (bs, 3
H), 2.2-2.3 (m, 2H), 2.92 (dd,
1H), 3.16 (d, 2H), 5.64 (d, 1
H), 5.71 (bd, 1H)

Next, preparation examples are shown. Parts represent parts by weight. Formulation Example 1 20 parts of the compound of the present invention are dissolved in 65 parts of xylene, and 15 parts of emulsifier Sorpol 3005X (trade name of Toho Chemical Co., Ltd.) are added and mixed well with stirring to obtain a 20% emulsion.

Formulation Example 2 40 parts of the compound of the present invention were added to sorbol 3005X (described above) 5
Parts, and mixed well. Carplex # 80 (trade name of Shionogi & Co., Ltd., synthetic hydrous silicon oxide fine powder) 32
And 23 parts of 300-mesh diatomaceous earth were added and stirred and mixed with a Juice mixer to obtain a 40% wettable powder.

Formulation Example 3 1.5 parts of the compound of the present invention and AGSORBLVM-MS
98.5 parts of 24/48 (baked product of montmorillonite manufactured by OILDRI, granular carrier having a particle size of 24 to 48 mesh) are added and mixed well to obtain 1.5% granules.

Formulation Example 4 10 parts of the compound of the present invention, 10 parts of phenylxylylethane and 0.5 part of Sumidur L-75 (Tolylene diisocyanate manufactured by Sumitomo Bayer Urethane Co., Ltd.) are mixed, and then gum arabic is added. It is added to 20 parts of a 10% aqueous solution and stirred with a homomixer to obtain an emulsion having an average particle size of 20 μm. Next, 2 parts of ethylene glycol is added thereto, and the mixture is further reacted in a hot bath at 60 ° C. for 24 hours to obtain a microcapsule slurry. On the other hand, 0.2 parts of Xanthan gum,
Gum R (Sanyo Chemical Aluminum Magnesium Silicone)
G) Disperse 1.0 part in 56.3 parts of ion-exchanged water to obtain a thickener solution. The above microcapsule thriller 42.5
And 57.5 parts of the thickener solution to give 10% microcapsules.

Formulation Example 5 After mixing 10 parts of the compound of the present invention and 10 parts of phenylxylylethane, a 10% aqueous solution of polyethylene glycol 2
0 parts and stirred with a homomixer to obtain an average particle size of 3 μm.
m of emulsion are obtained. On the other hand, Xanthan gum 0.2
1.0 part of Vegum R (aluminum magnesium silicate manufactured by Sanyo Chemical Co., Ltd.) is dispersed in 58.8 parts of ion-exchanged water to obtain a thickener solution. 40 parts of the above emulsion and 60 parts of the thickener solution are mixed to obtain a 10% flowable.

Formulation Example 6 5 parts of the compound of the present invention were mixed with 3 parts of Carplex # 80 (trade name of Shionogi & Co., Ltd., synthetic hydrous silicon oxide fine powder), PAP
Add 0.3 parts and 91.7 parts of 300 mesh talc,
Stir and mix with a juice mixer to obtain a 5% powder.

Formulation Example 7 0.1 part of the compound of the present invention is dissolved in 10 parts of dichloromethane and mixed with 89.9 parts of Isopar M (manufactured by Isoparaffin Exxon Chemical) to obtain a 0.1% oil solution.

Formulation Example 8 One part of the compound of the present invention, 0.01 part of BHT, 5 parts of dichloromethane and 33.99 parts of deodorized kerosene are mixed and dissolved, filled in an aerosol container, and a valve part is attached. 60 parts of a propellant (liquefied petroleum gas) is charged under pressure to obtain an oily aerosol.

Formulation Example 9 0.1 part of the compound of the present invention and 49.9 parts of deodorized kerosene are mixed and dissolved, filled in an aerosol container, a valve is attached, and a propellant (liquefied petroleum gas) is passed through the valve. /
50 parts of a 50/50 mixture of dimethyl ether) are charged under pressure to give an oily aerosol.

Formulation Example 10 0.6 part of the compound of the present invention, 0.01 part of BHT, 5 parts of xylene
Parts, deodorized kerosene 3.39 parts and emulsifier @ Atmos 300
(Registered trade name of Atlas Chemical Co., Ltd.) # 1 An aerosol container was charged with a mixture of 1 part and 50 parts of pure water, and a valve was attached. Through the valve, 40 parts of a propellant (liquefied petroleum gas) were passed. Under pressure to obtain an aqueous azole.

Formulation Example 11 0.1 g of the compound of the present invention is dissolved in 20 ml of acetone, and uniformly mixed with 99.9 g of a carrier for mosquito coil (mixed in a ratio of 4: 3: 3 of tub flour: lees flour: wood flour). After stirring and mixing, water 120
Then, the resulting mixture is molded and dried to obtain a mosquito coil.

Formulation Example 12 Acetone is added to 0.2 g of the compound of the present invention, 0.1 g of BHT, and 0.4 g of piperonyl butoxide to make 10 ml with total. 0.5 ml of this solution is 2.5 cm x
A 1.5 cm-thick and 0.3 cm-thick electric mat substrate (a fibril of a mixture of cotton linter and pulp solidified into a plate) is uniformly impregnated to obtain an electric mosquito repellent.

Formulation Example 13 0.2 parts of the compound of the present invention and 0.1 part of BHT were mixed with deodorized kerosene 9
9.7 parts of the solution was obtained by dissolving it in a vinyl chloride container, and the upper part was heated with a heater to absorb the liquid (inorganic powder was solidified with a binder and sintered). ) Is inserted to obtain a part used for the liquid-absorbing core type heat evaporation device.

Formulation Example 14 100 mg of the compound of the present invention was dissolved in an appropriate amount of acetone.
A 4.0 cm × 4.0 cm, 1.2 cm thick porous ceramic plate is impregnated to obtain a heated smoker.

Formulation Example 15 A filter paper is impregnated with an acetone solution of the compound of the present invention at a concentration of 1 g per 1 m ^{2 of the} compound of the present invention, and the acetone is air-dried to obtain an anti-mite sheet.

Test Example 1 (Mosquito incense test against Culex pipiens) After mixing an acetone solution of the compound of the present invention with a mixed incense base (meal flour: wood flour, 4: 3: 3) so as to have a predetermined dose, , And water was added thereto, and a sufficiently kneaded product was obtained by molding and drying), and the substrate was air-dried to obtain a mosquito coil. Culex pipiens pallens female adult 1
0 mice were released into a cubic glass chamber (volume 0.34 m ³ ) of 70 cm on a side. 0.3 g of the mosquito coil containing the compound of the present invention prepared in accordance with the above was placed in the incense stand on the center of the chamber floor, ignited from one end, and taken out of the chamber after burning for 30 seconds. Fifteen minutes after the installation of the incense stick, the state of knockdown of Culex pipiens was observed. Also, (S) -2-methyl-4-oxo-3- (2-propynyl) -cyclopent-2-enyl (1RS) -cis-3- (2,2-dichlorovinyl) -2,2-dimethylcyclo The same test was conducted for propane carboxylate (hereinafter, referred to as control compound A). Table 1 shows the results
Shown in The knockdown activity in the table is shown based on the following criteria. ◎: All insects were knocked down (total of 2 repetitions) ○: 1 to 3 insects that were not knocked down (the same) Δ: 4 to 6 insects that were not knocked down (the same) ×: Knocked down 7 or more insects

[Table 1]

Test Example 2 Spraying Test of Oil Agent on Culex pipiens Culex pipiens pallens 10 adult female cubs (Culex pipiens pallens) were cubic glass chambers with a side length of 70 cm (volume 0.34).
m ³ ) released within. 0.7 ml of the oil solution containing the compound of the present invention having a predetermined concentration (described in the table) prepared according to Formulation Example 7 was sprayed into the chamber from the small window on the side of the chamber with a spray gun. Two minutes after spraying, the state of knockdown of Culex pipiens was observed. Also, (S) -2-methyl-4-oxo-3- (2-propynyl) -cyclopent-2-enyl (1RS) -cis-3- (2,2-dichlorovinyl) -2,2-dimethylcyclo The same test was conducted for propane carboxylate (hereinafter, referred to as control compound A). Table 1 shows the results. The knockdown activity in the table is shown based on the following criteria. ：: 3 or less insects not knocked down (total of 2 repetitions) △: 4 to 6 insects not knocked down (same) ×: 7 or more insects not knocked down (same)

[Table 2]

Test Example 3 Insecticidal activity against cockroaches and toxicity to rats <Insecticidal activity against cockroaches> 1.0 μl of a diluted acetone solution of the compound of the present invention and control compound A was applied to the chest abdominal plate of female adult cockroaches, using a micro applicator. After feeding water and food, the number of surviving and dead insects after 72 hours was investigated, and the LD ₅₀ (mg / kg) was determined from the mortality rate.
The value was determined. <Toxicity to rat> Compound of the present invention and control compound A
Was diluted to a predetermined concentration with corn oil, the diluted solution was administered 10 ml / kg to male rats, given water and food, survival after 7 days, to investigate the number of deaths, LD ₅₀ (mg from the mortality /
kg). <Calculation of safety coefficient> The safety coefficient was calculated from the insecticidal activity against the cockroach and the toxicity to rats by the following formula. Table 3 shows the results. Safety factor = {toxicity (LD ₅₀ value) against rat} / {insecticidal activity (LD ₅₀ values) for the American cockroach}

[Table 3]

Test Example 4 Aerosol Test on Housefly A house fly (Musca domestica) of about 100 adults (male: female ≒ 1: 1) was placed on an imitation paper on the floor and a cubic test chamber (1.8 m per side) (5 m2) was prepared. .8 m ³ ), Formulation Example 9
An oily aerosol of the compound of the present invention prepared in accordance with
It was sprayed four times so as to become 5 g. After spraying 2,3,5
After 7, 10 and 15 minutes, the number of house flies that had been knocked down was counted, and the KT ₅₀ value (the time required for 50% of the test insects to be knocked down) was determined from the obtained data. Twenty minutes after spraying, the test insects were collected in a cup, sugar water was given thereto, and after 24 hours, the death or death was observed, and the mortality was determined. The test was performed in four replicates. As a result, the KT ₅₀ value was about 2 minutes, and the mortality was 100%.

Test Example 5 Liquid Mosquito Removal Test for Culex pipiens A glass tube (height: 12 cm, diameter: 4 cm, 20 cm in diameter) containing 20 adult Culex pipiens pallens females on the top of a metal cylinder having a height of 80 cm and a diameter of 20 cm (Closed with a nylon net). The glass tube was placed on a metal plate having a hole with a diameter of 4 cm at the top of the cylinder to allow airflow from below to escape. Parts used in a liquid-absorbing-wick-type heat evaporation apparatus of the present compound prepared according to Formulation Example 13 (concentration of the present compound in a liquid preparation of 0.2
%) Was set in a commercially available liquid-absorbing wick-type heating and evaporating apparatus (liquid mosquito collection) and installed at the bottom of the cylinder. The apparatus was energized, and after 7 minutes of energization, the state of knockdown of the test insects was observed. As a result, all the test insects were knocked down. In addition,
The test was performed in duplicate.

[0043]

INDUSTRIAL APPLICABILITY The compound of the present invention is excellent in pest control effect and safety for mammals, and is extremely useful as an active ingredient of a pest control agent, particularly, a pest control agent for epidemic control.

Claims (6)

[Claims] [Claim 1] Formula 1 (S) -2-methyl-4-oxo-3- (2
-Propynyl) -cyclopent-2-enyl (1R)
-Trans-3- (2,2-dichlorovinyl) -2,2
-Dimethylcyclopropane carboxylate compound. 2. A pesticidal composition comprising the compound according to claim 1. 3. The pest control agent according to claim 2, wherein the pest control agent is a pest control agent for epidemic control. 4. The pesticidal composition according to claim 2, wherein the pesticidal composition is an insecticide or acaricide. 5. The compound according to claim 1, wherein the amount of the compound is 0.001 to 9;
The pest control agent according to any one of claims 2 to 4, which contains 5% by weight. 6. A method for controlling insect pests, comprising using the compound according to claim 1.