JP2002020209A - Mosquito controlling agent containing ester compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an excellent mosquito controlling agent containing an ester compound, especially a controlling agent against Culex pipiens pallens and provide the ester compound. SOLUTION: The mosquito controlling agent contains an ester compound of general formula (I) (R1 is H, a (halogen-substituted)1-10C alkyl or the like) as an active component.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a mosquito controlling agent containing an ester compound and the ester compound.

[0002]

An object of the present invention is to provide an excellent mosquito control agent.

[0003]

Means for Solving the Problems The present inventors have conducted intensive studies in order to find an excellent mosquito control agent, and as a result, have found that an ester compound represented by the following general formula (I) is contained as an active ingredient. The present inventors have found that a characteristic mosquito controlling agent has excellent efficacy, and reached the present invention. That is, the present invention provides a compound represented by the general formula (I):

Embedded image (Wherein, R ¹ represents a hydrogen atom, a C1-C10 alkyl group optionally substituted with a halogen atom, a C3-C10 alkenyl group optionally substituted with a halogen atom, a C3 optionally substituted with a halogen atom. -C10 alkynyl group, C4-C10 optionally substituted with a halogen atom
C3-C8 cycloalkyl group optionally substituted by cycloalkyl group, halogen atom or C1-C3 alkyl group C1-C3 alkyl group, halogen atom or C
A phenyl group optionally substituted with a 1-C3 alkyl group, a phenyl (C1-C3) alkyl group optionally substituted with a halogen atom or a C1-C3 alkyl group,
A furanyl (C1-C3) alkyl group optionally substituted with a halogen atom or a C1-C3 alkyl group, a thienyl (C1-C3) alkyl group optionally substituted with a halogen atom or a C1-C3 alkyl group, a halogen atom C1-C5 alkoxy C1 optionally substituted with
-Represents a C1-C5 alkyl group or a C1-C5 alkylthio C1-C5 alkyl group which may be substituted with a halogen atom. The present invention provides a mosquito controlling agent characterized by containing an ester compound represented by the formula (1) as an active ingredient (hereinafter referred to as the controlling agent of the present invention). Further, the present invention also provides an ester compound as the active ingredient.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION First, an ester compound represented by the general formula (I) which is an active ingredient of the controlling agent of the present invention will be described.

In the present invention, examples of the C1-C10 alkyl group which may be substituted with a halogen atom represented by R ¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, an isobutyl group, 2,
2-dimethylpropyl group, decyl group and 2,2,2-
A trifluoroethyl group is mentioned, and as the C3-C10 alkenyl group optionally substituted with a halogen atom,
Examples include an allyl group and a 3-chloro-2-propenyl group, and C3 which may be substituted with a halogen atom.
Examples of the -C10 alkynyl group include a propargyl group and the like, and C10 which may be substituted with a halogen atom.
Examples of the 4-C10 cycloalkyl group include a cyclobutyl group and the like, and a halogen atom or C1-C3
Examples of the C3-C8 cycloalkyl C1-C3 alkyl group which may be substituted with an alkyl group include a cyclobutylmethyl group, a (1-methylcyclopropyl) methyl group and a (2,2-dichlorocyclopropyl) methyl group. Examples of the phenyl group which may be substituted with a halogen atom or a C1-C3 alkyl group include a phenyl group.
Phenyl optionally substituted with an alkyl group (C1-C
3) Examples of the alkyl group include a benzyl group, a 4-chlorobenzyl group, and a phenethyl group. Examples of the furanyl (C1-C3) alkyl group optionally substituted with a halogen atom or a C1-C3 alkyl group include: Examples thereof include a 2-furanylmethyl group. Examples of a thienyl (C1-C3) alkyl group which may be substituted with a halogen atom or a C1-C3 alkyl group include, for example, 2-
Thienylmethyl may be mentioned, and the (C1-C5 alkoxy) C1-C5 alkyl group optionally substituted with a halogen atom may be, for example, a 2-methoxyethyl group,
Examples of the (C1-C5 alkylthio) C1-C5 alkyl group optionally substituted with a halogen atom include a methylthiomethyl group.

The ester compound represented by the general formula (I) includes an optical isomer (R, S) based on an asymmetric carbon, a geometric isomer (E, Z) based on a C = N double bond, and a cyclopropane ring. Geometric isomers (cis, trans) exist,
The ester compound represented by the general formula (I) includes all of these optical isomers, geometric isomers, and mixtures thereof.

The compound represented by the general formula (I) can be prepared by, for example, the following (Production method 1), (Production method 2) or (Production method 3)
Can be produced by the method shown in FIG.

(Production method 1) General formula (II)

Embedded image (Wherein R ¹ has the same meaning as described above), and a compound represented by the formula (III):

Embedded image A method of producing by reacting with an alcohol compound represented by the formula:

The reaction is carried out in the presence of a condensing agent, usually in a solvent.
If necessary, the reaction can be performed in the presence of a base. Examples of the condensing agent used in the reaction include dicyclohexylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, and reagents prepared from diethylazodicarboxylate and triphenylphosphine. . In this reaction, a solvent inert to the reaction can be used. Specific examples include hydrocarbons such as toluene and hexane, ethers such as diethyl ether and tetrahydrofuran, and halogens such as dichloromethane and 1,2-dichloroethane. Hydrocarbons, and mixed solvents thereof. As the base used in this reaction, for example, triethylamine, pyridine,
Organic bases such as N, N-diethylaniline, 4-dimethylaminopyridine, diisopropylethylamine and the like can be mentioned. The range of the reaction time is usually from instant to 72 hours.
The range of the reaction temperature is from -20 ° C to 100 ° C (when the boiling point of the solvent is 100 ° C or lower, the boiling point of the solvent used in the reaction). The alcohol compound represented by the formula (III) used in the reaction can achieve its purpose at 1 mol with respect to 1 mol of the carboxylic acid represented by the general formula (II).
It can vary from 0.5 to 1.5 moles. When this reaction is carried out in the presence of a condensing agent, the amount of the condensing agent used in the reaction is usually 1 mol per 1 mol of the carboxylic acid represented by the general formula (II), but may vary depending on the situation of the reaction. Can change. Further, the amount of the base used in the present reaction can be an arbitrary amount according to the situation of the reaction. After the reaction, the ester compound represented by the general formula (I) can be obtained, for example, by the following method. (1) A post-treatment such as concentration of the reaction mixture after extraction with an organic solvent is performed, and if necessary, chromatography,
A method of performing a purification operation such as distillation. (2) A method in which the reaction solution is directly concentrated and, if necessary, further subjected to purification operations such as chromatography and distillation.

(Production Method 2) A method of reacting an acid chloride of a carboxylic acid represented by the general formula (II) with an alcohol compound represented by the formula (III) The reaction is usually carried out in a solvent in the presence of a base in a solvent. It is done in.
Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N, N-diethylaniline, 4-dimethylaminopyridine, and diisopropylethylamine. In this reaction, a solvent inert to the reaction can be used. Specific examples include hydrocarbons such as toluene and hexane, ethers such as diethyl ether and tetrahydrofuran, and halogens such as dichloromethane and 1,2-dichloroethane. Hydrocarbons and mixed solvents thereof can be used. The range of the reaction time is usually from instant to 72 hours. The reaction temperature range is usually -20.
The range is from 100 ° C to 100 ° C (when the boiling point of the solvent is 100 ° C or lower, the boiling point of the solvent used in the reaction). The alcohol compound represented by the formula (III) used in the reaction can achieve its purpose with 1 mol per 1 mol of the carboxylic acid represented by the general formula (II), but is usually 0.5 to 1.5.
It can vary in the molar range. The base used in the reaction can achieve the purpose of 1 mol per 1 mol of the reactive derivative of the carboxylic acid represented by the general formula (II), but can be changed according to the reaction situation.
After the reaction, a general post-treatment operation such as pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the mixture, and if necessary, further performing a purification operation such as chromatography and distillation to obtain the compound represented by the general formula (I) ) Can be obtained.

(Production Method A-3) A carboxylic acid compound represented by the general formula (II) and a compound represented by the formula (I)
A method of reacting a sulfonic acid ester of an alcohol compound represented by II). The reaction is usually performed in the presence of a base and usually in a solvent.
As the base used in the reaction, for example, sodium-
Examples thereof include alkali metal alkoxides such as t-butoxide, and inorganic bases such as potassium hydroxide and sodium hydride. In this reaction, a solvent inert to the reaction can be used, and specific examples include an organic sulfur compound such as dimethyl sulfoxide, an organic phosphorus compound such as hexamethylphosphorotriamide, water, and a mixture thereof. Can be The range of the reaction time is usually from instant to 24 hours. The range of the reaction temperature is from -20 ° C to 100 ° C (when the boiling point of the solvent is 100 ° C or lower, the boiling point of the solvent used in the reaction). The sulfonic acid ester of the alcohol compound represented by the formula (III) used for the reaction is represented by the general formula (I)
The purpose can be achieved with 1 mol per 1 mol of the carboxylic acid compound represented by I), but it can usually be changed in the range of 0.5 to 1.5 mol. After the reaction, a general post-treatment operation such as pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the mixture, and if necessary, further performing a purification operation such as chromatography and distillation to obtain the compound represented by the general formula (I) ) Can be obtained.

The starting compounds used in (Production methods 1) to (Production method 3) can be produced by the following methods. (1) A carboxylic acid compound represented by the general formula (III) or a reactive derivative thereof is prepared by the method described in J. Chem. Soc.
2470 (1970), JP-A-54-160343 or JP-A-56-120661. (2) The alcohol compound represented by the formula (III) and its sulfonic acid ester are described in, for example, Pest. Sc
i. 11, 202 (1980) or JP-A-53-3
It can be produced according to the method described in Japanese Patent No. 4756.

Next, the control agent of the present invention will be described. The control agent of the present invention is intended to kill mosquitoes and repel mosquitoes. As the control agent of the present invention, the ester compound represented by the general formula (I) may be used as it is, but usually, the ester compound represented by the general formula (I) is formulated and used. Examples of the preparations include oils, emulsions, wettable powders, flowables (water suspensions, emulsions in water, etc.), granules, powders, aerosols, heat evaporation agents (mosquito repellents, mosquito repellent mats, liquid absorbent cores). Heated transpiration insecticide, etc.), Heated smoker (Self-burning type smoker, Chemical reaction type smoker, Perforated ceramic plate smoker, etc.), Non-heated transpiration agent (Resin transpiration, Impregnated paper transpiration, etc.) , Aerosols (such as foking), ULV agents and baits. Examples of the method of formulation include the following methods. (1) A method in which an ester compound represented by the general formula (I) is mixed with a solid carrier, a liquid carrier, a gaseous carrier, a bait, and the like, and if necessary, a surfactant and other formulation auxiliary agents are added and processed ( 2) A method of impregnating an ester compound represented by the general formula (I) into a base material such as a mosquito coil or an electric mosquito coil which does not contain an active ingredient. (3) An ester compound represented by the general formula (I) and a mosquito coil or an electric stick. A method of forming and processing after mixing with a base material such as a mosquito collecting mat. In these preparations, the ester compound represented by the general formula (I) is usually added in a weight ratio of 0.001 depending on the form of the preparation.
It contains 1-95%.

Examples of the solid carrier used in the formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fusami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (cellulose). Fine powder or granular materials such as cite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc., and chemical fertilizers (ammonium sulfate, phosphorous ammonium, nitrate, urea, salt ammonium, etc.). For example, water, alcohols (such as methanol and ethanol), ketones (such as acetone and methyl ethyl ketone), aromatic hydrocarbons (such as benzene, toluene, xylene, ethylbenzene, and methylnaphthalene), and aliphatic hydrocarbons (such as hexane and cyclohexane) , Kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile Isobutyronitrile), 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 oils such as cottonseed oil and the like. Examples of the gaseous carrier, that is, propellant, for example, Freon gas, Butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas, and the like. As the surfactant, for example, an alkyl sulfate salt,
Examples thereof include alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. Other pharmaceutical auxiliaries include, for example, casein, gelatin, polysaccharides (starch, gum arabic,
Cellulose derivatives, alginic acid, etc.), lignin derivatives,
Bentonite, sugar, synthetic water-soluble polymer (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acid, etc.), PAP (acidic isopropyl phosphate), BHT
(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, Fatty acids or esters thereof are exemplified. As the base material of the mosquito coil, for example, wood powder, vegetable powder such as flour and tub powder, starch,
A mixture with a binder such as glutein can be mentioned. Examples of the base material of the electric mosquito collecting mat include those obtained by solidifying cotton linter in a plate shape, those obtained by solidifying fibrils of a mixture of cotton linter and pulp in a plate shape, and the like. Examples of the base material of the self-combustion type smoke agent include combustion exothermic agents such as nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethylcellulose, and wood flour; alkali metal salts; alkaline earth metal salts; Examples include chromate, a pyrolysis stimulant such as chromate, an oxygen supply agent such as potassium nitrate, a flame retardant such as melamine and wheat starch, a bulking agent such as diatomaceous earth, and a binder such as a synthetic paste. Examples of the base material of the chemical reaction type smoke agent include exothermic agents such as sulfides, polysulfides, hydrosulfides, hydrated salts and calcium oxide of alkali metals, catalysts such as carbonaceous substances, iron carbide, and activated clay. Agents, azodicarbonamide, benzenesulfonyl hydrazide, dinitrosopentamethylenetetramine, organic foaming agents such as polystyrene and polyurethane, and fillers such as natural fiber pieces and synthetic fiber pieces. Examples of the base material of the non-heated evaporant include thermoplastic resins (polyester, polyamide, ethylene-vinyl chloride copolymer, ethylene-vinyl acetate copolymer, ethylene-methyl methacrylate copolymer, etc.), paper (filter paper). , Japanese paper, high-quality paper, note paper, dust paper, cardboard, etc.), and cloth (nonwoven fabric, etc.). Examples of bait baits include, for example, cereal flour, vegetable oil, sugar, bait components such as crystalline cellulose, dibutylhydroxytoluene, antioxidants such as nordihydroguaseletic acid, preservatives such as dehydroacetic acid, and pepper powder. Examples include an anti-feeding agent for children and pets, and a pest-inducing flavor such as cheese flavor, onion flavor, and peanut oil.

The method of using the preparation of the control agent of the present invention includes:
For example, the following methods are mentioned, and the method can be appropriately selected according to the dosage form of the preparation, the place of use, and the like. (1) A method in which the preparation is treated as it is in the place where the pests live. (2) A method of diluting a preparation with a solvent such as water and then treating the preparation at a habitat of a pest. (3) A method in which the preparation is heated in a place where the pests live.

The pesticidal composition of the present invention is effective against mosquitoes (for example, Culex pipiens such as Culex pipiens), Aedes such as Aedes aegypti and Aedes albopictus, Anopheles such as Aedes aegypti and midges, but not limited to mosquitoes and other pests. Also has effect. Among the other pests against which the pesticidal agent of the present invention exerts a controlling effect, examples of pests (harmful insects and harmful mites) include the following. Hemiptera: Insects such as planthoppers (brown planthoppers, brown planthoppers, brown planthoppers, etc.), leafhoppers (etc.), aphids, stink bugs, whiteflies, beetles, grubworms, psyllids, etc. (Spodoptera, Scutellaria, Noctuidae, etc.), armyworms (Spodoptera litura, Armyworm, armyworm, etc.), white butterflies (Mont. White butterfly, etc.), squid moths (Kokakumonamamaki, etc.), Singing moths, Lepidoptera, Squid worms, Auricularis Agrotis spp.) (Kabayaaga, Tamanayaga etc.), Helicoverpa spp., Heliothis pest (Heliothis spp.), Konaga, Ichimon dissely, Iga, Koiga, etc. Diptera: Pteratoids, sarcophaga, flies (Seed D, little house fly, onion maggot, etc.), fruit flies,
Drosophila, Drosophila, Flies, Blackflies,
Flies, flies, etc.

Coleopteran pests: corn rootworms (Western corn rootworm, Southern corn rootworm, etc.), scarab beetles (Duchenne buoy, etc.), weevil (Koku weevil, rice weevil, etc.)
(Epilachna spp., Epilach sp.) Bark beetles, long beetles, longhorn beetles,
Blue-winged beetle, etc. Lepidopteran insects: German cockroaches, black cockroaches, brown cockroaches, flying cockroaches, cockroach cockroaches, etc. Kind,
Orthoptera (Hymenoptera), etc. Orthoptera: Pests, Grasshoppers, etc. Orthoptera: Pests such as human flea, cat flea Lice: Pests such as human lice, lice, etc. Isoptera: Termites, house termites, etc.

Pests of the order Isopoda: Pterodactyla japonica, Echinacea purpurea, P. occidentalis etc. Pests of the order Polypoda: Plumbaceae etc.
p.) etc.

Mites: Dermatophagoides (Dermatophagoides farinae, Dermatophagoides farinae, etc.), Dermatophagoids (Dermatophagoides farinae, Scarabidae, etc.), Ticks mite (Tirinicus mites, House dust mites, Sanitary mites, etc.), Tick mites (Lepidoptera mites, etc.), , House spider mites, spider mites (Nerd spider mite, Kanzawa spider mite, mandarin spider mite, apple spider mite, etc.), and ticks (Phaseopid spider mite, etc.). The control agent of the present invention is also effective for pests having resistance to existing insecticides and acaricides.

The insecticide of the present invention includes other insecticides, acaricides, nematicides, soil insecticides, fungicides, herbicides, plant growth regulators, repellents, synergists, fertilizers, soil conditioners. Can be mixed or used together.

Examples of such insecticides, nematicides, acaricides, and soil pest control agents include, for example, fenitrothion [O,
O-dimethyl O- (3-methyl-4-nitrophenyl)
Phosphorothioate], phenthione [O, O-dimethyl O- (3-methyl-4- (methylthio) phenyl) phosphorothioate], diazinone [O, O-diethyl-O-2-isopropyl-6-methylpyrimidine-4-
Yl phosphorothioate], chlorpyrifos [O, O-
Diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate], acephate [O, S-dimethylacetylphosphoramidothioate], methidathion [S-2,3-dihydro-5-methoxy-2-oxo-
1,3,4-thiadiazol-3-ylmethyl O, O-
Dimethyl phosphorodithioate], disulfoton [O,
O-diethyl S-2-ethylthioethyl phosphorodithioate], dichlorophos [2,2-dichlorovinyl dimethyl phosphate], sulphophos [O-ethyl O-4]
-(Methylthio) phenyl S-propyl phosphorodithioate], cyanophos [O-4-cyanophenyl O, O
-Dimethyl phosphorothioate], dimethoate [O,
O-dimethyl-S-methylcarbamoylmethyl phosphorodithioate], fentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate],
Malathion [diethyl (dimethoxyphosphinothioylthio) succinate], trichlorfon [dimethyl 2,
2,2-trichloro-1-hydroxyethylphosphonate], azinphosmethyl [S-3,4-dihydro-4-
Oxo-1,2,3-benzotriazin-3-ylmethyl O, O-dimethylphosphorodithioate], monocrotophos [dimethyl-{(E) -1-methyl-2- (methylcarbamoyl) vinyl) phosphate], Organic phosphorus compounds such as ethion [O, O, O ', O'-tetraethyl-S, S'-methylenebis (phosphorodithioate)],

BPMC (2-sec-butylphenylmethylcarbamate), benfracarb [ethyl N-
{2,3-dihydro-2,2-dimethylbenzofuran-
7-yloxycarbonyl (methyl) aminothio} -N
-Isopropyl-β-alaninate], propoxur [2-isopropoxyphenyl methyl carbamate], carbosulfan [2,3-dihydro-2,2-
Dimethyl-7-benzo [b] furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1
-Naphthyl-N-methyl carbamate], methomil [S
-Methyl-N- (methylcarbamoyloxy) thioacetimidate], ethiophenecarb [2- (ethylthiomethyl) phenylmethylcarbamate], aldicarb [2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyloxime], Carbamate compounds such as oxamil [N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide] and phenothiocarb [S-4-phenoxybutyl-N, N-dimethylthiocarbamate];

Etofenprox [2- (4-ethoxyphenyl) -2-methyl-1- (3-phenoxybenzyl) oxypropane], 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 [(R
S) -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 (1RS, 3
Z) -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-valinate], bifenthrin [2-methyl-3-
Phenylbenzyl (1RS, 3Z) -cis-3- (2
-Chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate], halfenprox [2- (4-bromodifluoromethoxyphenyl) -2-methyl-1- ( 3-phenoxybenzyl) oxypropane], tralomethrin [(S) -α-cyano-3-phenoxybenzyl (1
R) -cis-3- (1,2,2,2-tetrabromoethyl) -2,2-dimethylcyclopropanecarboxylate], silafluofen [(4-ethoxyphenyl)-
{3- (4-fluoro-3-phenoxyphenyl) propyl} dimethylsilane], d-phenothrin [3-phenoxybenzyl (1R) -cis, trans-2,2-
Dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate], cyphenothrin [(R
S) -α-Cyano-3-phenoxybenzyl (1R)
-Cis, trans-2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate], d-resmethrin [5-benzyl-3-furylmethyl (1R) -cis, trans-2, 2-dimethyl-
3- (2-methyl-1-propenyl) cyclopropanecarboxylate], acrinasulin [(S) -α-cyano-3-phenoxybenzyl (1R, 3Z) -cis-
(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, 3Z) -cis-3-
(2-chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate], transfluthrin [2,3,5,6-tetrafluorobenzyl (1R) -trans -3- (2,2
-Dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], tetramethrin [3,4,5,6
-Tetrahydrophthalimidomethyl (1RS) -cis, trans-2,2-dimethyl-3- (2-methyl-
1-propenyl) cyclopropanecarboxylate],
Allethrin [(1RS) -cis, trans-2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylic acid (RS) -2-methyl-4-oxo-3- (2-propenyl) -2-cyclopentene-1
-Yl], empentrin [(RS) -1-ethynyl-
2-methyl-2-pentenyl (1R) -cis, trans-2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate], imiprothrine [2,5-dioxo-3- (2-propynyl) imidazolidin-1-ylmethyl (1R) -cis, trans-2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate], d-framethrin [5- (2-propynyl) furfuryl (1R)-
Cis, trans-2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate], 5- (2-propynyl) furfuryl 2,2
Pyrethroid compounds such as 3,3-tetramethylcyclopropane carboxylate,

Buprofezin [2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-
Thiadiazine derivatives such as thiadiazin-4-one], nitroimidazolidine derivatives, cartap [S, S'-
(2-dimethylaminotrimethylene) bis (thiocarbamate)], thiocyclam [N, N-dimethyl-1,
Nereistoxin derivatives such as 2,3-trithian-5-ylamine] and bensultap [S, S'-2-dimethylaminotrimethylene di (benzenethiosulfonate)], N-cyano-N'-methyl-N N-cyanoamidine derivatives such as'-(6-chloro-3-pyridylmethyl) acetamidine; endosulfan [6,7,8,9,
10,10-hexachloro-1,5,5a, 6,9,9
a-Hexahydro-6,9-methano-2,4,3-benzodioxathiepin-3-oxide], γ-BHC
[1,2,3,4,5,6-hexachlorocyclohexane], dicophor [1,1-bis (4-chlorophenyl)]
Chlorinated hydrocarbon compounds such as -2,2,2-trichloroethanol] and chlorofluazuron [1- {3,5-dichloro-4- (3-chloro-5-trifluoromethylpyridine-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] and the like.

Amitraz [N-methyl-bis (2,4-
Xyliminomethyl) amine], thiourea derivatives such as diafenthiuron [N- (2,6-diisopropyl-4-phenoxyphenyl) -N′-t-butylthiourea], N-phenylpyrazole Compound, 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], propargite [2- (4-tert-butylphenoxy) cyclohexylprop-2-ylsulfite], fenbuta Tin oxide [bis [tris (2-
Methyl-2-phenylpropyl) tin peroxide],
Hexythiazox [(4RS, 5RS) -5- (4-chlorophenyl) -N-cyclohexyl-4-methyl-2
-Oxo-1,3-thiazolidine-3-carboxamide], clofentezine [3,6-bis (2-chlorophenyl) -1,2,4,5-tetrazine], pyridaben [2-tert-butyl-5- (4-tert-butylbenzylthio) -4-chloropyridazine-3 (2H)-
On], fenpyroximate [tert-butyl]
(E) -4-[(1,3-Dimethyl-5-phenoxypyrazol-4-yl) methyleneamino-oxymethyl]
Benzoate], tebufenpyrad [N-4-tert]
-Butylbenzyl) -4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide], polynactin complex [tetranactin, dinactin, trinactin], pyrimidifen [5-chloro-N- [2-
{4- (2-ethoxyethyl) -2,3-dimethylphenoxy} ethyl] -6-ethylpyrimidin-4-amine], milbemectin, abamectin, ivermectin, azadirachtin [AZAD], and the like.

As the repellent, for example, 3,4-caranediol, N, N-diethyl-m-toluamide, 2- (2
-Hydroxyethyl) -1-piperidinecarboxylic acid 1-
Plant essential oils such as methylpropyl, p-menthane-3,8-diol, hyssop oil and the like;

As the synergist, for example, bis- (2,
3,3,3-tetrachloropropyl) ether, N-
(2-ethylhexyl) bicyclo [2,2,1] hept-5-ene-2,3-dicarboximide, α- [2-
(2-butoxyethoxy) ethoxy] (piperonyl butoxide) and the like.

[0028]

EXAMPLES Hereinafter, Production Examples, Preparation Examples and Test Examples will be given,
The present invention will be described in more detail, but the present invention is not limited to only these examples.

First, a production example of the ester compound represented by the general formula (I) will be described. In addition, the numbers of the ester compounds represented by the general formula (I) are those described in the following (Table 1) to (Table 8).

Production Example 1 (1R) -cis-3-((E) -methoxyimino)-
2,2-dimethylcyclopropanecarboxylic acid and (1R)
0.50 g of a 1: 1 mixture with -cis-3-((Z) -methoxyimino) -2,2-dimethylcyclopropanecarboxylic acid, (S) -4-hydroxy-3-methyl-2
-(2-propenyl) -2-cyclopenten-1-one 0.50 g, 4-dimethylaminopyridine 0.06 g,
The mixture of 12 ml of tetrahydrofuran was stirred under ice cooling, and 1-ethyl-3- (3-dimethylaminopropyl) was stirred.
0.90 g of carbodiimide hydrochloride was added. One day later, water was poured into the reaction solution, and the mixture was extracted with tert-butyl methyl ether. The organic layer is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then concentrated under reduced pressure. The obtained residue is subjected to silica gel column chromatography (developing solvent: hexane / ethyl acetate = 4/1). , (1R) -cis-3-((E) -methoxyimino)
-2,2-dimethylcyclopropanecarboxylic acid (S)-
2-methyl-4-oxo-3- (2-propenyl) -2
-Cyclopenten-1-yl (Compound No. 42) and (1
R) -cis-3-((Z) -methoxyimino) -2,2
0.75 g (84%) of a 1: 1 mixture of -dimethylcyclopropanecarboxylic acid (S) -2-methyl-4-oxo-3- (2-propenyl) -2-cyclopenten-1-yl (Compound No. 62) I got

According to the method described in Production Example 1, a 1: 1 mixture of the compounds of the present invention 10, 30, 83 and 103 was obtained.

Production Example 2 (1R) -trans-3-((E) -methoxyimino)
-2,2-dimethylcyclopropanecarboxylic acid and (1
R) -trans-3-((Z) -methoxyimino)-
1: 1 with 2,2-dimethylcyclopropanecarboxylic acid
0.34 g of (±) -4-hydroxy-3-methyl-2- (2-propenyl) -2-cyclopentene-
0.40 g of 1-one, 0.58 of triphenylphosphine
g of a mixture of 30 ml of tetrahydrofuran was stirred under ice cooling, and 1.2 ml of diisopropyl azodicarboxylate (40% toluene solution) was added. One day later, the residue obtained by concentration under reduced pressure was subjected to silica gel column chromatography (eluent: hexane / ethyl acetate = 4/1) to give (1R) -trans-3-((E) -methoxy). (Imino) -2,2-dimethylcyclopropanecarboxylic acid (RS) -2-methyl-4-oxo-3- (2-propenyl) -2-cyclopenten-1-yl (Compound No. 8)
2) 0.12 g (20% yield) and (1R) -trans-
3-((Z) -methoxyimino) -2,2-dimethylcyclopropanecarboxylic acid (RS) -2-methyl-4-oxo-3- (2-propenyl) -2-cyclopentene-
0.12 g of 1-yl (Compound No. 102) (Yield 20
%).

Examples of the ester compound represented by the general formula (I) are shown in Tables 1 and 2 together with the compound numbers. In Tables 1 to 8, the configuration of the alcohol moiety means the absolute configuration at the 1-position of the 2-cyclopentenone ring in the ester compound represented by the general formula (I),
The steric configuration of the acid moiety is defined as the absolute configuration at the 1-position of the cyclopropane ring and the relative configuration of the substituent at the 3-position of the cyclopropane ring with respect to the substituent at the 1-position of the cyclopropane ring in the ester compound represented by the general formula (I). And the relative configuration of the geometric isomers derived from the C = N double bond.

[0034]

Embedded image (I)

[0035]

[Table 1]

[0036]

[Table 2]

[0037]

[Table 3]

[0038]

[Table 4]

[0039]

[Table 5]

[0040]

[Table 6]

[0041]

[Table 7]

[0042]

[Table 8]

Next, the physical properties of the compound represented by formula (I) are shown below. Compound 10 ¹ H-NMR (C
DCL ₃ , TMS standard, unit: δ is ppm, J is Hz)
δ1.23 (3H, s), 1.29 (3H, s),
1.92 (1H, d, J = 5.5), 2.05 (3H,
s), 2.19 to 2.26 (2H, m), 2.98 (1
H, dd, J = 18.7, 6.3), 3.01 (2H,
d, J = 6.3), 4.54 (2H, d, J = 5.
7), 5.00 (1H, brs), 5.04 (1H,
dd, J = 7.0, 1.3), 5.22 (1H, dd,
J = 10.6, 1.0), 5.29 (1H, dd, J =
15.8, 1.0), 5.66-5.82 (2H,
m), 5.98 (1H, ddt, J = 15.98, 1
0.6, 6.3), 7.28 (1H, d, J = 7.6)

Compound 30 ¹ H-NMR (CDCl ₃ , T
MS standard, unit: δ is ppm, J is Hz) δ1.25
(3H, s), 1.31 (3H, s), 1.79 (1
H, d, J = 5.5), 2.05 (3H, s), 2.2
4 (1H, dd, J = 18.8, 1.7), 2.73
(1H, dd, J = 7.6, 5.5), 2.89 (1
H, dd, J = 18.8, 6.3), 2.99 (2H,
d, J = 6.2), 4.60 (2H, d, J = 5.
6), 5.00 (1H, brs), 5.04 (1H,
dd, J = 6.3, 1.7), 5.20 (1H, dd,
J = 10.3, 1.3), 5.33 (1H, dd, J =
17.0, 1.3), 5.69-5.84 (2H,
m), 6.00 (1H, ddt, J = 17.0, 10.
3,6.2), 6.39 (1H, d, J = 7.6)

1: 1 mixture of compound 42 and compound 62
¹ H-NMR (CDCl ₃ , TMS standard, unit: δ is pp
m and J are Hz) δ 1.26 (1.5 H, s), 1.2
7 (1.5H, s), 1.33 (3H, s), 1.88
(0.5H, d, J = 8.6), 1.93 (0.5H,
d, J = 8.6), 2.02 (3H, s), 2.03
(0.5H, dd, J = 8.9, 8.6), 2.26
(1H, br d, J = 18.6), 2.50 (0.5
H, dd, J = 8.6, 7.7), 2.88 (1H, d
d, J = 18.6, 6.3), 2.99 (2H, d, J)
= 6.3), 3.85 (1.5H, s), 3.91
(1.5H, s), 5.00 (1H, brs), 5.
05 (1H, m), 5.65 to 5.85 (2H, m),
7.00 (0.5H, d, J = 7.7), 7.70
(0.5H, d, J = 8.6)

Compound 82 ¹ H-NMR (CDCl ₃ , T
MS standard, unit: δ is ppm, J is Hz) δ1.23
(3H, s), 1.29 (1.5H, s), 1.32
(1.5H, s), 1.91 (1H, d, J = 5.
5), 2.01 (1.5H, s), 2.05 (1.5
H, s), 2.20 to 2.29 (2H, m), 2.86.
(0.5H, dd, J = 18.7, 6.4), 2.89
(0.5H, dd, J = 18.7, 6.4), 2.99
(2H, d, J = 6.2), 3.84 (3H, s),
4.99-5.06 (2H, m), 5.66-5.84
(2H, m), 7.22 (1H, d, J = 7.0)

Compound 102 ¹ H-NMR (CDCl ₃ ,
TMS standard, unit: δ is ppm, J is Hz) δ1.2
4 (1.5H, s), 1.25 (1.5H, s), 1.
31 (1.5H, s), 1.32 (1.5H, s),
1.77 (0.5H, d.J = 5.5), 1.78
(0.5H, d.J = 5.5), 2.02 (1.5H,
s), 2.04 (1.5H, s), 2.24 (0.5
H, dd, J = 18.6, 2.0), 2.32 (0.5
H, dd, J = 18.6, 2.0), 2.70 (0.5
H, dd, J = 7.9, 5.5), 2.71 (0.5
H, dd, J = 7.9, 5.5), 2.82 to 2.93.
(1H, m), 2.99 (2H, d, J = 6.2),
3.90 (3H, s), 4.99-5.06 (2H,
m), 5.68-5.83 (2H, m), 6.34.
(0.5H, d, J = 7.9), 6.35 (0.5H,
d, J = 7.9)

Next, formulation examples are shown. Parts represent parts by weight, and the ester compounds represented by the general formula (I) are shown in Tables 1 to 8
Is shown by the compound number.

Formulation Example 1 Emulsion Ten parts of each of the ester compounds 1 to 160 represented by the general formula (I) are dissolved in 35 parts of xylene and 35 parts of dimethylformamide, and 14 parts of polyoxyethylenestyrylphenyl ether and 14 parts of dodecyl Add 6 parts of calcium benzenesulfonate and mix well with stirring.
A 0% emulsion is obtained. Formulation Example 2 Wettable powder 20 parts of each of the ester compounds 1 to 160 represented by the general formula (I) are mixed with 4 parts of sodium lauryl sulfate, 2 parts of calcium ligninsulfonate, and a fine powder of synthetic hydrous silicon oxide 20.
And 54 parts of silicon earth were mixed and stirred with a juice mixer to obtain a 20% wettable powder for each.

Formulation Example 3 Granules 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 30 parts of clay are added to 5 parts of each of the ester compounds 1 to 160 represented by the general formula (I). Add and mix well with stirring. Then, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain 5% granules of each. Formulation Example 4 Powder One part of each of the ester compounds 1 to 160 represented by the general formula (I) is dissolved in an appropriate amount of acetone, and 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 part of PAP and clay 9 are added thereto.
Add 3.7 parts, stir and mix with a juice mixer, evaporate off acetone to obtain 1% powder for each.

Formulation Example 5 Flowable agent White carbon 3 containing 10 parts of each of the ester compounds 1 to 160 represented by the general formula (I) and 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt.
5 parts and 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain each 10% flowable agent. Formulation Example 6 Oil solution 0.1 part of each of the ester compounds 1 to 160 represented by the general formula (I) is dissolved in 10 parts of dichloromethane, and this is mixed with 89.9 parts of deodorized kerosene to prepare a 0.1% oil solution of each. Get.

Formulation Example 7 Oily aerosol One part of each of the ester compounds 1 to 160 represented by the general formula (I), 5 parts of dichloromethane and 34 parts of deodorized kerosene are mixed and dissolved, and the mixture is filled in an aerosol container. After mounting, 60 parts of a propellant (liquefied petroleum gas) is filled under pressure through the valve to obtain each oily aerosol. Formulation Example 8 aqueous aerosol 0.6 part of each of the ester compounds 1 to 160 represented by the general formula (I), 5 parts of xylene, 3.4 parts of deodorized kerosene, and an emulsifier {Atmos 300 (trade name of Atlas Chemical Co.)} 1 And 50 parts of pure water are filled into an aerosol container, a valve part is attached to the container, and 40 parts of propellant (liquefied petroleum gas) is filled under pressure through the valve part to prepare each aqueous aerosol. Get.

Formulation Example 9 Incense Incense A 0.5 g acetone solution of each of the ester compounds 1 to 160 represented by the general formula (I) was added to an incense base material (tab powder: meal powder: wood powder in a ratio of 4: 3: 3). 120 g of water was added to 99.5 g of the incense carrier that had been mixed in a uniform ratio and uniformly mixed, and the mixture was thoroughly kneaded and molded and dried), and the substrate was air-dried to obtain an incense stick for killing insects and mites. . Formulation Example 10 Electric Mosquito-Carrying Mat Acetone is added to 0.8 g of each of the ester compounds 1 to 160 represented by the general formula (I) and 0.4 g of piperonyl butoxide to make a total of 10 ml. 0.5 ml of this solution is 2.5 cm × 1.5 cm, thickness 0.3 c
m of the electric mat (a fibril of a mixture of cotton linter and pulp solidified into a plate) is uniformly impregnated to obtain each electric mosquito-removing matting agent.

Formulation Example 11 Absorbent wick type heat transpiration insecticide 3 parts of each of the ester compounds 1 to 160 represented by the general formula (I) are dissolved in 97 parts of deodorized kerosene, put into a vinyl chloride container, and By inserting a liquid-absorbing core (inorganic powder solidified with a binder and sintered) which can be heated by a heater, each liquid-absorbing core type heat-penetrating insecticide is obtained. Formulation Example 12 Heat-smoking agent 100 mg of each of the ester compounds 1 to 160 represented by the general formula (I) is dissolved in an appropriate amount of acetone, and 4.0 cm ×
Each of the heated smokers is obtained by impregnating a 4.0 cm, 1.2 cm thick porous ceramic plate.

Formulation Example 13 Poison Bait 10 mg of each of the ester compounds 1 to 160 represented by the general formula (I) is dissolved in 0.5 ml of acetone, and the resulting solution is fed to a solid feed powder for animals (solid feed powder for breeding and breeding, CE-
2. Treat to 5g and mix uniformly. The acetone is then air-dried to obtain each 0.2% poison bait.

Formulation Example 14 Acaricide sheet Each of the ester compounds 1 to 160 represented by the general formula (I) was dissolved in an appropriate amount of acetone, and the solution was added to a nonwoven fabric at a rate of 1 / m ^2.
g, and then impregnated with acetone to obtain each mite-proof sheet. Formulation Example 15 Microcapsules 10 parts each of the ester compounds 1 to 160 represented by the general formula (I), 10 parts of phenylxylylethane, and 0.5 part of Sumidur L-75 (tolylene diisocyanate manufactured by Sumitomo Bayer Urethane Co., Ltd.) Is added to 20 parts of a 10% aqueous solution of gum arabic, followed by stirring 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 warm bath at 60 ° C. for 24 hours to obtain a microcapsule slurry. Separately, 0.2 part of Xanthan gum and 1.0 part of Vegum R (aluminum magnesium silicate manufactured by Sanyo Chemical) are dispersed in 56.3 parts of ion-exchanged water to obtain a thickener solution. 42.5 parts of the above microcapsule slurry and 57.5 parts of the thickener solution are mixed to obtain 10% microcapsules.

Next, test examples show that the control agent of the present invention is useful as a mosquito control agent. In addition, the ester compounds represented by the general formula (I) are represented by the compound numbers in Tables 1 and 2.

Test Example 1 According to Formulation Example 6, Compound Nos. 10, 30, (82 and 1
02 (1: 1 mixture) and (1: 1 mixture of 83 and 103) were adjusted to 0.025% (W / V). Ten female adults of Culex pipiens are released into a cubic glass chamber (volume 0.34 m ² ) of 70 cm on a side, and 0.7 ml of the above oil agent is sprayed through a small window on the side of the chamber with a spray gun at 8.8 × 10 ⁴ Pa. Sprayed in the chamber with pressure. Ten minutes after spraying, the number of knocked-down insects was counted. As a result, all of the tested compounds knocked down 90% or more of the insects (two repetitions).

[0059]

EFFECT OF THE INVENTION By using the controlling agent of the present invention, excellent mosquito controlling activity can be obtained.

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4H006 AA01 AB02 BJ10 BJ50 BM10 BM71 BM72 BP10 BR70 KA06 4H011 AC02 BA01 BA02 BC01 BC02 BC03 BC04 BC06 BC07 BC08 BC11 BC18 BC19 BC20 BC22 DA02 DA06 DA07 DA10 DA13 DA15 DA21 DC05 DB05 DC DC06 DC08 DD05 DE05 DE07 DE16 DH03 DH10 DH14

Claims (3)

[Claims] 1. A compound of the general formula (I) (Wherein, R ¹ represents a hydrogen atom, a C1-C10 alkyl group optionally substituted with a halogen atom, a C3-C10 alkenyl group optionally substituted with a halogen atom, a C3 optionally substituted with a halogen atom. -C10 alkynyl group, C4-C10 optionally substituted with a halogen atom
C3-C8 cycloalkyl C1-C3 alkyl group optionally substituted by cycloalkyl group, halogen atom or C1-C3 alkyl group, halogen atom or C1
A phenyl group optionally substituted with a -C3 alkyl group,
A phenyl (C1-C3) alkyl group optionally substituted with a halogen atom or a C1-C3 alkyl group, a furanyl (C1-C3) alkyl group optionally substituted with a halogen atom or a C1-C3 alkyl group, a halogen atom Or a thienyl (C1-C3) alkyl group optionally substituted with a C1-C3 alkyl group, a C1-C5 alkoxy C1-C optionally substituted with a halogen atom,
Represents a 5-alkyl group or a C1-C5 alkylthio C1-C5 alkyl group optionally substituted with a halogen atom. A mosquito control agent comprising an ester compound represented by the formula (1) as an active ingredient. 2. A pest control agent of Culex pipiens, characterized by containing an ester compound represented by the general formula (I) as an active ingredient. (3) (1R) -trans-3-((E) -methoxyiminomethyl) -2,2-dimethylcyclopropanecarboxylic acid (S) -3- (2-propenyl) -2-methyl-4- Oxo-2-cyclopentenyl, (1R) -trans-3-((Z) -methoxyiminomethyl) -2,
2-dimethylcyclopropanecarboxylic acid (S) -3-
(2-propenyl) -2-methyl-4-oxo-2-cyclopentenyl, (1R) -trans-3-((E)-
(Ethoxyiminomethyl) -2,2-dimethylcyclopropanecarboxylic acid (S) -3- (2-propenyl) -2-
Methyl-4-oxo-2-cyclopentenyl, (1R)
-Trans-3-((Z) -ethoxyiminomethyl)-
2,2-dimethylcyclopropanecarboxylic acid (S) -3
-(2-propenyl) -2-methyl-4-oxo-2-
Cyclopentenyl, (1R) -trans-3-((E)
-Allyloxyiminomethyl) -2,2-dimethylcyclopropanecarboxylic acid (S) -3- (2-propenyl)
-2-methyl-4-oxo-2-cyclopentenyl,
(1R) -trans-3-((Z) -allyloxyiminomethyl) -2,2-dimethylcyclopropanecarboxylic acid (S) -3- (2-propenyl) -2-methyl-4-
Oxo-2-cyclopentenyl, (1R) -cis-3-
((E) -methoxyiminomethyl) -2,2-dimethylcyclopropanecarboxylic acid (S) -3- (2-propenyl) -2-methyl-4-oxo-2-cyclopentenyl, (1R) -cis- 3-((Z) -methoxyiminomethyl) -2,2-dimethylcyclopropanecarboxylic acid selected from the group consisting of (S) -3- (2-propenyl) -2-methyl-4-oxo-2-cyclopentenyl Any compound.