WO1999015491A1

WO1999015491A1 - Ester compounds and pest-controlling agents containing the same as the active ingredient

Info

Publication number: WO1999015491A1
Application number: PCT/JP1997/003400
Authority: WO
Inventors: Tomonori Iwasaki; Kazunori Tsushima; Mikako Nakamachi
Original assignee: Sumitomo Chemical Company, Limited
Priority date: 1996-03-28
Filing date: 1997-09-25
Publication date: 1999-04-01
Also published as: JP3826480B2; ZA979098B; JPH09316035A

Abstract

Ester compounds of general formula (I) which have an excellent pest-controlling effect and therefore are useful as the active ingredient for pest-controlling agents. In said formula R is C1-C5 alkyl, C2-C5 alkenyl or C2-C5 alkynyl.

Description

Description Ester compounds and pesticides containing them as active ingredients

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

Background art

Conventionally, for example, Japanese Patent Publication No. 55-425-45 discloses that certain ester compounds are used as active ingredients such as insecticides. However, these compounds are not always always sufficient as active ingredients such as insecticides in terms of insecticidal efficacy.

Disclosure of the invention

Under these circumstances, the present inventors have conducted intensive studies to find a compound having an excellent pest control effect, and as a result, the ester compound represented by the following general formula 1 has an excellent pest control effect. Thus, the present invention has been completed.

That is, the present invention provides a compound represented by the following general formula 1:

[Wherein, R represents a C i Cs alkyl group (eg, a methyl group, an ethyl group, an isopropyl group, etc.), a C ₂ -C ₅ alkenyl group (eg, an aryl group, 3-butenyl) A C ₂ -C ₅ alkynyl group (eg, propargyl group, 3-butynyl group, etc.). ]

And a pesticidal composition comprising the same as an active ingredient.

Embodiment of the Invention

The compounds of the present invention include stereoisomers (R / S) and geometric isomers (E / Z), but the present invention includes all stereoisomers having pest control activity, And mixtures thereof.

Among HC of the compound of the present invention represented by the general formula 1, a compound in which R is an ethyl group, an aryl group or a propyl group is particularly preferable.

The compound of the present invention can be produced, for example, by the following method. Equation 2:

And a reactive derivative thereof represented by the general formula 3

R _{/ C} H ₃ H CH-OH

C

[Wherein, R represents the same meaning as described above. ]

Method _c for reacting with an alcohol compound represented by Examples of the reactive derivative of the carboxylic acid compound of the formula 2 include an acid halide, and preferably an acid chloride. The amount ratio of the raw materials used is usually 0.5 to 2 mol of the alcohol compound represented by the general formula 3 with respect to 1 mol of the sulfonic acid compound represented by the formula 2 or its reactive derivative.

When a carboxylic acid compound represented by the formula 2 itself is reacted with an alcohol compound represented by the general formula 3, the reaction is usually carried out by dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethyl). In the presence of a dehydrating agent such as (aminopropyl) carbodiimide hydrochloride (WSC), the reaction is usually carried out in an organic solvent such as chloroform, dichloromethane, tetrahydrofuran (THF), benzene or toluene. The amount of the dehydrating agent to be used is generally 1 to 5 mol per 1 mol of the carboxylic acid compound represented by the formula 2 or a reactive derivative thereof. The reaction may be carried out in the presence of an organic base such as pyridine, triethylamine, 4-dimethylaminopyridine or diisopropylethylamine. The reaction temperature is usually in the range of from 10 ^DC to + 100 ° C or the boiling point of the organic solvent used, preferably in the range of from 0 ° C to 30 ° C.

The reaction of the carboxylic acid compound represented by the formula 2 or its reactive derivative with the alcohol compound represented by the general formula 3 is usually carried out in an organic solvent such as dichloromethane, tetrahydrofuran (THF), benzene, and toluene. The reaction is performed in the presence of a base such as gin, triethylamine and 4-dimethylaminopyridine. The amount of the base to be used is generally 1 to 5 mol, per 1 mol of the carboxylic acid compound represented by the formula 2 or the reactive derivative thereof. The reaction temperature is usually in the range of from 10 ° C to + 100 ° C or the boiling point of the organic solvent used, preferably from 0 ° C to + 30 ° C. After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent, washing, and concentration to isolate the target compound of the present invention. If necessary, it may be further purified by a usual operation such as chromatography.

The sulfonic acid compound represented by the formula 2 which is one of the intermediates for producing the compound of the present invention can be prepared, for example, according to the method described in Bull. Chem. Soc. Jpn, 4385-4394 (1987). Can be manufactured.

The alcohol compound represented by the general formula 3, which is another intermediate in producing the compound of the present invention, can be produced, for example, according to the description in U.S. Pat.No. 4,263,463. .

Examples of pests against which the compound of the present invention exerts control effects include the following harmful insects and mites.

Hemiptera:

Black-billed beetle power, brown beetle power, mosquitoes such as staghorn planthoppers, Tsumaguroyo-ki, Inazuma-kobayashi, Japanese white-headed tuna, etc., aphids, stink bugs, whiteflies, scale insects, hornworms, etc.

Lepidopteran pests:

Ponds such as Nikameiga (Polygonidae), Kobunomeiga and Noshimekokuga, Spodoptera such as Spodoptera litura, Acapoto, Spodoptera, etc .; Agrotis spp., Heliothis spp., Konaga, Iga, Koiga etc.

Psocoptera pests:

House powers such as acaie power, kogatakae power, netaishima power, and hitos Butterflies such as Zishima, etc., Anopheles such as Shinahamadara, Usurika, Houseflies such as house fly, oye fly, Himee fly, etc. Drosophila, tabby, bu, flies, etc.

Coleoptera pests:

コーン Corn roots such as estancon worms, Southern corn worms, etc., Scarabaeidae such as Dupanebuoyi, Himekogane etc. , Beetles such as leaf beetles, beetles, beetles, Epilachna spp, such as tentacled beetles, beetles beetles, beetles beetles, beetles beetles, beetles beetle, etc.

Reptile pests:

Chinese cockroaches, black cockroaches, red cockroaches, flying cockroaches, spring cockroaches, etc.

Pterodactyl pests:

Southern yellow thistle, yellowtail thistle, etc.

Hymenoptera pests:

Oribats, wasps, wasps and wasps such as wasps Orthoptera:

Kera, grasshopper, etc.

Pteratoid pests:

Human flea, etc.

Lice pests:

Human lice, lice, etc. Isoptera pests:

Yamato termite, house termite, etc.

Harmful insects such as

Two kinds:

Nisenamihadani, Namihadani, Kanzahadani, Citrus spider mite, Apple Hadani etc.

Ticks:

Red tick

House dust mites:

Acarid mites, house dust mites, red mite, house mite, etc.

Harmful mites such as

When the compound of the present invention is used as an active ingredient of a pesticidal agent, it is usually necessary to mix it with a solid carrier, liquid carrier, gaseous carrier, or bait, or impregnate it into a base material such as mosquito coil or mat. If necessary, add surfactants and other pharmaceutical auxiliaries to add oils, emulsions, wettable powders, suspensions in water, emulsions in water, etc., granules, powders, aerosols, etc. Mosquito coils, electric mosquito coils, no mats (liquid electric mosquito coils: liquid-absorbent wicking device for insecticide), etc., self-burning type smokers, chemical reaction type smokers, porous ceramics It is formulated into non-heated fumigants, such as heated fumigation agents such as plate fumigation agents, resin evaporants and impregnated paper evaporants, fogging agents such as fogging, ULV agents, and poison baits.

These preparations usually contain the compound of the present invention as an active ingredient in an amount of 0.001 to 95% by weight.

Examples of solid carriers used in the formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, fubasami clay, acid clay, etc.), talcs, ceramics, and other inorganic minerals (cericite). The stone Fine powders or granular materials such as British, sulfur, activated carbon, calcium carbonate, hydrated silica, etc., and chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, salt ammonium, etc.). Examples of the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons

(Benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, gas oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile) Ryl, isopyronitrile, 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, cottonseed oil and other plant oils. Examples of the gaseous carrier, that is, propellant, include chlorofluorocarbon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenates, polyethylene glycol ethers, and polyhydric alcohol esters. And sugar alcohol derivatives.

Examples of pharmaceutical adjuvants such as fixatives and dispersants include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginate sugar), lignin derivatives, bentonite, sugars, and synthetic water-soluble polymers. (Polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.). Examples of stabilizers include PAP (isopropyl acid phosphate) and BHT (2,6-di-tert-butyl-14-methylphenol). ), BHA (2-tert-butyl-4-methoxyphenol and 3-tert-butyl-14-methacrylate) A mixture with xyphenol), vegetable oils, mineral oils, 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 cake flour with a binder such as tub flour, starch, glutin and the like.

Examples of the base material of the electric mosquito collection include a plate-like solidified fibril of a cotton linter or a mixture of a cotton linter and pulp.

The base components of the self-burning type smoke agent include, for example, combustion heating agents such as nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethylcellulose, and wood flour; alkali metal salts; alkaline earths Thermal decomposition stimulants such as metal salts, dichromates and chromates; oxygen supply agents such as potassium nitrate; flame retardants such as melamine and wheat starch; extenders such as diatomaceous earth; binders such as synthetic paste Are listed.

The base components of the chemical reaction type smoke agent include, for example, exothermic agents such as sulfides of alkali metals, polysulfides, hydrosulfides, hydrated salts, calcium oxide, carbonaceous materials, iron carbide, activated clay, etc. Examples include catalyst agents, organic blowing agents such as azodicarbonamide, benzenesulfonylhydrazide, 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 thermoplastic resin, filter paper, Japanese paper, and the like.

The base components of poison bait include, for example, bait components such as cereal flour, vegetable oil, sugar, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; and pepper. Powders, etc., and preventive agents such as cheese flavor, onion flavor, peanut oil, etc. Can be

Formulations of flowables (water suspensions or emulsions) generally contain 1 to 75% of the compound in 0.5 to 15% of a dispersant, 0.1 to 10% of a suspension aid (eg, protected colloids). (A compound that imparts thixotropy), 0 to 10% of suitable auxiliary agents (for example, antifoaming agent, antibacterial agent, stabilizer, spreading agent, penetration aid, antifreezing agent, antibacterial agent, antibacterial agent) It can be obtained by finely dispersing in water containing a fungicide. Instead of water, it is also possible to use an oil in which the compound hardly dissolves as an oil suspension. 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 preparation thus obtained is used as it is or diluted with water or the like. Also mixed with or without other pesticides, acaricides, nematicides, soil pesticides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners Can be used simultaneously.

Other insecticides and acaricides used include, for example, Huunitrothion

[0,0—Dimethyl 0— (3-Methyl-1-4-nitrophenyl) phosphorothioate], Fenthion [0,0—Dimethyl 0— (3-Methyl-4-1

(Methylthio) phenyl) phosphorothioate], diazinon [0,0-Jetyl-1 0-2-isopropyl-1 6-methylpyrimidine-1 4-ylphosphorothioate], chlorpyrifos [0,0-Jetyl-0 0-3,5,6] —Organic phosphorus compounds such as trichloromethyl 2-pyridyl phosphorothioate] and DDVP [2,2-dichlorovinyldimethyl phosphate];

BPMC [2-sec-butylmethylcarbamate Ί, Propoxy Carbamate compounds such as sulf [2-isopropoxyphenyl N-methylcarbamate];

Ethopenprox [2- (4-Ethoxyphenyl) -12-methylpyrroyl-3-phenoxybenzyl ether], phanvalerate [(RS) — 1-Thano-3-phenoxybenzyl (RS) -2 -(4-chlorophenyl) -1-methylbutyrate], esfenvalerate [(S) -a-cyano-3-phenyloxybenzyl (S) —2— (4-cyclophenyl) 1-3 —Methylbutyrate], phenylpropatrin [(RS) —Hycyan-1-3-phenyloxybenzyl 2,2,3,3-tetramethylcyclopropane lipoxylate], cypermethrin [(RS) — 1-cyano 13-phenoxybenzyl (1RS-cis, trans) 13- (2,2-dichlorovinyl) 1,2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1RS —Cis, trance) I3 (2, 2-dichloro-vinyl) one 2, 2-dimethyl-cyclopropanecarboxylate rate, Derutame tri emissions [(S) - Fei one Shiano 3- phenoxyethanol benzyl

(1R-cis) 1-3- (2,2-dibromovinyl) 1,2,2-dimethylcyclopropanecarboxylate], 2-methyl-2- (4-bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) Ether, tralomethrin [(1R-cis) 3 [(l'RS) (Γ, 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-phenotrine [3-phenoxybenzyl (1R-cis, trans) -chrysanthemate], siphenotriene [(RS) —α-cyano-3-phenoxybenzyl (1 R—cis, 9/15 1

Trans) -Chrysanthemate], d-resmethrin [5-benzyl-13-furylmethyl (1R-cis, trans) -chrysanthemate], acrinasulin [(S) -α-cyano-3] Phenoxybenzyl (1 R—cis (Ζ)) — (2,2-dimethyl-13- {3-oxo-13- (1,1,1,3,3,3-hexafluoropropylo) Xy) propenyl} cyclopropane carboxylate], cyflutrine [(RS) -Hycianol 4-fluoro-3, -phenoxybenzyl 3- (2,2-dichlorovinyl) 1,2,2-dimethylcyclo Propane carboquinate], lambda halotrin [(RS)-1-cyano 3-phenoxybenzyl (1RS-cis (Ζ))-3-(2-1,3,3-trifluoroprobu 1-enyl) _2,

2-dimethylcyclopropanecarboxylate], tefluthrine [2,3,5,6-tetrafluoro-4-methylbenzyl (1RS-cis (Ζ))-

3-(2-Chloro-3,3,3-trifluoroprop-1-enyl) -1,2,2-dimethylcyclopropanecarboxylate], transfluthrin

[2,3,5,6-tetrafluorobenzyl (1R-trans) -13- (2,2-dichlorovinyl) -1,2,2-dimethylcyclopropanecarboxylate], brareslin [(S) -2 Methyl-4_oxo-1 3- (2-Provinyl) -1-2-Cyclopentene-1-yl (1R-cis, trans) -Chrisantemate, d-Areslin [2-Methyl-4-oxo-1 3-

(2-Propenyl) -12-cyclopentene-11-yl (1R-cis, trans) 1-closanthemate, d-tetramethrin [3,4,5,6-tetratetraphthalimidmethyl (1R- Pyrethroid compounds such as cis, trans) monochrysanthemate,

Ditromidazolidine, such as imidacloprid [1- (6-chloro-3-pyridylmethyl) -N-nitroimidazolidin-1-2-iridenamine] Derivative, chlorfluazurone [1- (3,5-dichloro-1-4- (3-chloro-1-5-trifluoromethylpyridine-12-yloxy) phenyl) -13- (2,6-difluor Lobenzoyl) ゥ rea], tefluvenzuron [1- (3,5-dichloro-1,2,4-difluorophenyl) 13- (2,6-difluorobenzoyl) ゥ rea], flufenoxuron 1— (4— (2-chloro-1-4-trifluoromethylphenoxy) -1-fluorophenyl] —3 -— (2,6-difluorobenzoyl) ゥ rea], difluvenzuron [1— ( Benzoyl phenyl urea compounds such as 4-chlorophenyl) 1-3- (2,6-difluorobenzoyl) urea], phenyl virazole compounds, methoxadiazone [5-methoxy] 3- (2-Methoxyphenyl) -1,3,4-oxadiazole-1 2 (3H) When the compound of the present invention is used as an active ingredient of an agricultural pesticide, the application rate is generally 0.1 to 500 g per 10 ares, and an emulsion, a wettable powder, a flowable and the like are usually used in water. When diluted, the application concentration is 0.1 to 1 000 ppm, and the granules, dusts, etc. are applied as is, without any dilution. Emulsions, wettable powders, flowables, etc. are diluted with water to 0.1-10000 ppm when used as an active ingredient for oils, aerosols, fumigants, smokers, transpirants, aerosols, ULV, etc. Etc. are applied as they are.

All of these application rates and concentrations vary depending on the type of preparation, application time, application place, application method, type of pest, degree of damage, etc., and can be increased or decreased without being affected by the above range. Or can be. Example

Hereinafter, the present invention will be described in more detail with reference to Production Examples, Formulation Examples, Test Examples, and the like, but the present invention is not limited to only these examples. First, Production Examples of the compound of the present invention will be described.

Production Example 1

(E)-(RS) — 3-Hydroxy-1-4-methyl-4-octene-1,7-diyne 300 mg, 2,6-di-tert-butyl-4-methylphenol 5 mg, pyridine 226 mg, 4-dimethylamino (Z)-(1RS, cis) -1,2,2-dimethyl-3- (2-chloro-1,3,3,3-trifluoroprobe) was added to a mixed solution of 5 mg of pyridine and 1 Om1 of toluene under ice-cooling. 525) 525 mg of cyclopropenecarboxylic acid chloride was added dropwise, and the reaction was continued at room temperature for 6 hours. Thereafter, the reaction solution was poured into ice-cooled 5% citric acid, extracted three times with ethyl ether, the ether layers were combined, washed successively with saturated saline, 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-14-octane-1,7 —Diyne-3-yl (Z) — (1RS, cis) -1,2,2-dimethyl-13- (2-chloro-1,3,3,3-trifluoropropenyl) cyclopropyl pancarboxylate (the present invention) Compound (7)) was obtained in a yield of 41%. no ²¹ 1.4748

Production Example 2

(E)-(RS) 1-3-Hydroxy-14-methyl-4,8-nonagene-1-in 300 mg, 2,6-ditert-butyl-4-methylphenol 5 mg, pyridine 202 mg, 4-dimethyl (Z) _ (1RS, cis) 1-2,2-dimethyl-3- (2-chloro-1,3-, 3-trifluoropropyl) in a mixed solution of 5 mg of aminopyridine and 10 ml of toluene under ice-cooling Penil) Cyclopropanecarboxylic acid chloride 47 Omg was added dropwise, and the reaction was continued at room temperature for 6 hours. Thereafter, the reaction solution was poured into ice-cooled 5% aqueous citric acid, Extracted three times with ethyl ether. The ether layers were combined, washed sequentially with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent: ethyl hexanoacetate mixture (30: 1)) to give (E) — (RS) —4-methyl-1,3,8-octagen-1-in-3-y (Z) — (1RS, cis) -1,2,2-dimethyl-13- (2-chloro-3,3,3-trifluoropropynyl) cyclopropanecarboxylate (Compound (3) of the present invention) in a yield of 88 %. η. ²³ 1.4685

Production Example 3

(Ε) — (RS) 1,3-hydroxy-14-methyl-4-heptene-11-in 1500 mg, 2,6-di-tert-butyl-4-methylphenol 1 Omg. Pyridine 202 mg, 4-dimethylaminopyridine (Z)-(1RS, cis) -1,2,2-dimethyl-3- (2-chloro-1,3,3,3-trifluoroprobe) was added to a mixed solution of 10 mg and toluene 5 Om1 under ice-cooling. G) 309 Omg of cyclopropanecarboxylic acid chloride was added dropwise, and the reaction was continued at room temperature for 6 hours. Thereafter, the reaction solution was poured into ice-cooled 5% aqueous solution of citric acid and extracted three times with getyl ether. The ether layers were combined, washed sequentially with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (developing solvent: hexane Z, ethyl acetate mixture (30: 1)) to give (E) — (RS) —4-methyl-4 — Yl (Z) — (1RS, cis) 1,2,2-dimethyl-13- (2-chloro-1,3,3,3-trifluoropropenyl) cyclopropanecarboxylate (Compound (5) of the present invention) 328 Omg (78% yield) was obtained. η. ²⁵ 1.4609

Next, specific examples of the compound of the present invention are shown together with the compound numbers. (1) (E)-(RS) — 4-Methyl-1-octene-1-in-3-yl (Z) — (1RS, cis) -1,2,2-Dimethyl-3- , 3,3-Trifluoropropenyl) cyclopropanecarboxylate

(2) (E)-(RS) —4,6-dimethyl-1-4-hepten-1-in —3-yl (Z)-(1RS, cis) 1,2,2-dimethyl-3- (2-k Loro 3,3,3-trifluoropropionyl) cyclopropanecarboxylate (3) (E) — (RS) — 4-Methyl-1,4,8-nonagene 1-in-3-yl (Z) — (1RS, cis) 1,2,2-Dimethyl-3- (2—chloro-1,3,3-trifluorotrifluoron) cyclopropanecarboxylate n _D ²³ 1.4685

(4) (E)-(RS) 1-4-Methyl-4-1-Nonene-1,8-Diin-1-3- (Z)-(1RS, cis)-1, 2, 2-dimethyl-1-(- 3,3,3-Trifluoropropenyl) cyclopropanecarboxylate

(5) (E)-(RS) -4-Methyl-4 -heptene-1-in-3-yl (Z)-(1RS, cis) -1,2,2-Dimethyl-3- (2-chloro-1,3- 3,3-trifluoropropenyl) cyclopropanecarboxylate η. ²⁵ 1.4609

(6) (Ε) ― (RS) —4-Methyl-1,3,7-butadiene 1-in-1 3-yl (—) — (1 RS, cis) 1,2,2-dimethyl-1 3— (2-chloro-1,3,3-trifluorotrifluoropropionyl) cyclopropanecarboxylate η. ²⁴ 1.4651

(7) (Ε) ― (RS) —4-Methyl-4-octene-1,7-diyne —3—yl (Ζ)-(1RS, cis) 1,2,2-dimethyl-3- (2-chloro) 1,3,3,3-trifluoropropionyl) cyclopropanecarboxylate n _D ²¹ 1.4748 15 1

(8) (E) 1 (S) -4 1-methyl-1 4-heptene 1- 1-in 1- 3-yl (Z)-(1RS, cis) 1-, 2-Dimethyl 3- (2- 3,3,3-Trifluoroprobenyl) cyclopropanecarboxylate

(9) (E)-(S) —4-Methyl-14-Heptene-11-In-3-yl (Z) — (1R, trans) -1,2,2-Dimethyl-1-3- (2-chloro口一 3,3,3-Trifluoropropenyl) cyclopropanecarboxylate

(10) (E) ― (S) 14-Methyl-14,7-Octadien-11-in-1-3-yl (Z) — (1RS, cis) 1,2,2-Dimethyl-1 3 -— (2 — 1,3,3—Trifluoroprobenyl) cyclopropanecarboxylate

(11) (E) ― (S) 14-Methyl-14-heptene-11-in-3-yl (Z) — (1R, cis) 1,2,2-dimethyl-3- (2-chloro-one 3, 3, 3-trifluorotrifluoropropionyl) cyclopropanecarboxylate

(12) (E) one (S) one 4-methyl-14-heptene-11-in-3-yl (Z) — (1RS—cis, trans) one, two, two-dimethyl one three— (two one) Chloro-3,3,3-trifluorotrifluoropropionyl cyclopropanecarboxylate

(13) (E) 1 (S) —4-Methyl-4-octene 1-in-3-yl (Z) — (1R, trans) -1,2,2-dimethyl-1 3— (2-chloro- 3, 3, 3—trifluoropropionyl) cyclopropanecarboxylate

(14) (E) ― (S) —4-Methyl-1,4,7-octacene-1-in-3-yl (Z) — (1R, trans) 1,2,2-Dimethyl-1 3 -— (2 — Chloro-3,3,3-trifluoropropenyl) cyclopropane carboxylate

Next, Formulation Examples of the compound of the present invention are shown. Note that “parts” represents parts by weight, and The compounds are indicated by the above compound numbers.

Formulation Example 1 Emulsion

20 parts of each of the compounds (1) to (14) are dissolved in 65 parts of xylene, and 15 parts of an emulsifier, Solpol 3005X (trade name of Toho Chemical Co., Ltd.), are added and mixed well to obtain a 20% emulsion of each.

Formulation Example 2 wettable powder

To 40 parts of each of Compounds (1) to (14), add 5 parts of Solpol 3005X (described above), mix well, and mix well. Carplex # 80 (registered trademark of Shionogi Pharmaceutical Co., Ltd., synthetic hydrous hydrated gay fine powder) 32 parts , 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

Add 1.5 parts of each of Compounds (1) to (14) and 98.5 parts of AGS0RBLVM-MS24 / 48 (fired product of Montmorillonite manufactured by OIL DRI, granular carrier having a particle size of 24 to 48 mesh), and mix well. 1.5% granules.

Formulation Example 4 Microcapsules

After mixing 10 parts of each of the compounds (1) to (14), 10 parts of fuirylxylylethane and 0.5 part of Sumidur L-75 (Tolylene disocyanate manufactured by Sumitomo Bayer Perethane Co., Ltd.), 20 parts of a 10% aqueous solution of gum arabic In addition, the mixture is stirred with a homomixer to obtain an emulsion having an average particle size of 20 zm. Next, 2 parts of ethylene glycol are added thereto, and the mixture is further reacted in a warm bath at 60 ° C for 24 hours to obtain a microcapsule slurry.

— On the other hand, disperse 0.2 part of Xanthan gum and 1.0 part of Vegum R (aluminum magnesium silicate manufactured by Sanyo Chemical) 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 the viscous solution 9

Mix to obtain each 10% microcapsule.

Formulation Example 5 Flowable

After mixing 10 parts of each of compounds (1) to (14) with 10 parts of phenyloxylylethane, the mixture is added to 20 parts of a 10% aqueous solution of polyethylene glycol, and stirred with a homomixer to obtain an emulsion having an average particle size of 3 μm. Get.

On the other hand, 0.2 part of Xanthan gum and 1.0 part of Vegum R (aluminum magnesium silicate manufactured by Sanyo Chemical) are 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 viscous agent solution are mixed to obtain each 10% flowable agent.

Formulation Example 6 Dust

Add 5 parts of each of compounds (1) to (14) to 3 parts of Carplex # 80 (above), 0.3 parts of PAP and 91.7 parts of 300 mesh talc, and stir and mix with a juice mixer to obtain each 5% powder.

Formulation Example 7 Oil

0.1 part of each of the compounds (1) to (14) is dissolved in 5 parts of dichloromethane, and this is mixed with 94.9 parts of deodorized kerosene to obtain each 0.1% oil solution.

Formulation Example 8 Oily aerosol

Mix and dissolve 1 part of each of compounds (1) to (14), 5 parts of dichloromethane and 34 parts of deodorized kerosene, fill an aerosol container, attach a valve part, and then use a propellant (liquefied petroleum gas) through the valve part. ) Fill 60 parts with pressure to obtain each oily aerosol.

Formulation Example 9 aqueous aerosol

0.6 parts of each of compounds (1) to (14), 5 parts of xylene, 3.4 parts of deodorized kerosene and emulsifier {ATMOS 300 (trade name of Atlas Chemical Co.)} 1 Parts and 50 parts of pure water are charged into an aerosol container, a vanoleb part is attached, and 40 parts of a propellant (liquefied petroleum gas) is filled under pressure through the valve part, and each aqueous aerosol is filled. Get.

Formulation Example 10 Mosquito coil

0.3 g of each of the compounds (1) to (14) was dissolved in 20 ml of acetone, and a carrier for mosquito coils (tab powder: kashiwa powder: wood powder mixed in a ratio of 4: 3: 3) was mixed with 99.7 g. After uniformly stirring and mixing, 12 Om 1 of water is added, and the well-kneaded one is molded and dried to obtain each mosquito coil.

Formulation example 11 Electric mosquito collection mat

Acetone is added to 0.8 g of each of compounds (1) to (14) and 0.4 g of piperonyl butoxide, and dissolved to make a total of 1 Om1. 0.5 ml of this solution was uniformly impregnated into a 2.5 cm x 1.5 cm, 0.3 cm thick electric mat substrate (solidified fibril of a mixture of cotton linter and pulp in a plate shape), and each electric Obtain mosquito repellent.

Formulation Example 12 Liquid Electric Mosquito Removal

3 parts of each of compounds (1) to (14) are dissolved in 97 parts of deodorized kerosene, put in a vinyl chloride container, and the upper part is made of a liquid-absorbing wick that can be heated with a heater. Sinter) to obtain each liquid electric mosquito.

Formulation Example 13 Heated smoker

10 Omg of each of the compounds (1) to (14) is dissolved in an appropriate amount of acetone and impregnated in a 4.0 cm x 4.0 cm, 1.2 cm thick porous ceramic plate to obtain each of the heated smokers.

Formulation Example 14 Room temperature volatile agent

Dissolve 100 g of each of compounds (1) to (14) in an appropriate amount of acetone, After evenly applying it to a filter paper of 2 cm x 2 cm and 0.3 mm thickness, air-dry acetone to obtain each room temperature evaporant.

Formulation Example 15 Anti-mite sheet

Compound (1) to each of the acetone dissolution dropwise impregnated such that lm ² per 1 g to filter paper (14), acetone and air dried to obtain each proof Danishito.

Next, Test Examples show that the compound of the present invention is useful as an active ingredient of a pesticidal agent. The compounds of the present invention have the above compound numbers, and the compounds used as comparative controls are shown by the compound symbols in Table 1.

Test Example 1 Insecticidal test of house flies by volatilization at room temperature

An aluminum dish with a diameter of 7 cm at the bottom was treated dropwise with 0.64 ml of a 0.004% diluted acetone solution of the test compound, and the acetone was air-dried. Release 10 CSMA housefly female adults into a polyethylene cap (diameter 9 cm, height 4.5 cm), and place a 16-mesh nylon net on the top to prevent the insects from directly touching the drug-treated surface. I covered it. Turn the cup upside down and After placing on a mini dish and elapse of 60 minutes at 25 ° C., the number of writhing insects was counted, and the percentage of writhing insects (percent moribund) was determined. As a result, the compounds (5), (6) and (7) of the present invention each showed a writhing insect rate of 100%. In contrast, the comparative compound (A) showed a writhing insect rate of 10%.

Claims

Scope of claim General formula 1:

[Where R is 〇! ~ (: ₅ alkyl group, a C ₂ -C ₅ alkenyl or C ₂ - C ₅ alkynyl group.

An ester compound represented by the formula:

2. The ester compound according to claim 1, wherein R is an ethyl group.

3. The ester compound according to claim 1, wherein R is an aryl group.

4. The ester compound according to claim 1, wherein R is a propyl group.

5. A pesticidal composition comprising the ester compound according to claim 1 as an active ingredient and a carrier.

6. A pest control method, which comprises applying an effective amount of the ester compound according to claim 1 to a pest or a habitat of the pest.