WO2002088099A1 - Thiazolylcinnamonitrile compound and pest control agent - Google Patents

Abstract

A compound represented by the formula [1]: [1] (wherein R represents hydrogen, C1-6 alkyl, a group represented by COR1 or CSR1, etc.; X represents halogeno, C1-6 alkyl, C3-6 cycloalkyl, C1-6 haloalkyl, etc.; Y represents nitro, cyano, halogeno, C1-6 alkyl, etc.; Z represents carbon or nitrogen; m is an integer of 0 to 7; and n is an integer of 0 to 5); and a pest control agent containing the compound or a salt thereof as the active ingredient.

Description

 Specification

 Thiazolyl cinnamate nitrile compounds and pesticides

The present invention is related to novel Chiazorirukei cinnamic acid nitrile compounds and pesticides _c

Background technology:

 Conventionally, many insecticides and acaricides have been used, but their efficacy is insufficient, their use is limited due to drug resistance problems, and phytotoxicity and contamination of plants are caused. Or, because of its high toxicity to humans, fish, and the like, it is not always a satisfactory control agent. Therefore, there is a need for the development of a drug that can be used safely with few such disadvantages.

 Acrylonitrile compounds similar to the compounds of the present invention are described in EP. 189960, WO 97/40009, WO 98/42683, WO 98/35935 and WO 99/44993.

 WO 01/21618 describes a compound represented by the following formula o

(Q represents a thiazolyl or the like substituted with a specific group, and A represents a phenyl group or the like which may be substituted.)

 However, the compound having a thiazolyl having a substituent of the present invention is not described. DISCLOSURE OF THE INVENTION:

An object of the present invention is to provide a novel compound which can be industrially advantageously synthesized, and which can be used as a pesticidal agent which has a certain effect and can be used safely. The present invention has the formula (1)

 [1]

[Wherein R is a hydrogen atom, a C i- ₆ alkyl group, a group represented by the formula COR i, a group represented by the formula CSR i, a group represented by S 0 ₂ R ₂ , a C ₆ alkoxy C alkyl group,

C 1-6 alkylcarbonyl O alkoxy C - ₆ alkyl group, C ₃ _ ₆ consequent opening alkyl carbonylation Ruokishi C _i-6 alkyl group, C ₆ alkoxycarbonyl O alkoxy C _i-6 alkyl group, substituted which may phenylalanine carbonyl O carboxymethyl C alkyl groups, C _i-6 alkyl Chio C _i-6 alkyl groups, C WINCH ₆ alkyl carbonylation thio C alkyl groups, C ₃ - ₆ cyclo alkyl carbonylation thio C _i-6 alkyl Group, a C- ₆ alkoxycarbonylthio C i- ₆ alkyl group, a phenylcarbonylthio C alkyl group which may have a substituent, a phenyl C ^ 6 alkyl group which may have a substituent,

It is C ₂ alkyl group, C ₃ - ₆ cycloalkyl group, - 6 haloalkyl group, d

— ₆ alkoxy group, C ₆ alkylthio group, Cs s alkylamino group, _δ- alkylamino group, optionally substituted phenyl 0 i-6 alkyl group, may have a substituent A phenyl group ₆ alkoxy group, a phenyl group which may have a substituent,

R ₂ represents a C i-u alkyl group or a phenyl group which may have a substituent,

It is Shiano group, a nitro group, a halogen atom, C ^ - to Table ₆ haloalkyl group, C _i-6 alkoxy group, a C i-6 haloalkoxy group - ₆ alkyl group, C ₃ - ₆ a cycloalkyl group, C ^ ,

Y is a nitro group, Shiano group, a halogen atom, - 6 alkyl group, _d-6 Haroaruki Le group, C 1-6 alkoxy groups, C _1-6 haloalkoxy group, C 1-6 alkylthio group, one ₆ alkylsulfinyl represents groups, C i-6 alkylsulfonyl group, C u alkylamino group, di-C _i-6 alkylamino group, C i-6 alkyl Cal Poni group, a C _i-6 alkoxycarbonyl group,

 Z represents a carbon atom or a nitrogen atom,

 m represents 0 or an integer from 1 to 7,

 n represents 0 or an integer of 1 to 5. ]

And a pesticidal composition comprising the compound or a salt thereof as an active ingredient. Embodiment of the invention:

 In the above formula [1],

 R is a hydrogen atom,

 Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl and its isomers, hexyl and its isomers

C! _ ₆ alkyl group,

Group of the formula COR!, A group represented by the formula CS Ri, a group represented by S 0 ₂ R _2, main Tokishimechiru, main Tokishechiru, Etokishechiru, ethoxymethyl, propoxy methyl, C alkoxy, such as Puchirokishimechiru C i — ₆ alkyl group,

§ Se Tokishimechiru, Viva Roy Ruo carboxymethyl, hepta Noi Ruo carboxymethyl, Aseto Kishechiru, C alkyl carbonylation Ruokishi 0 Bok ₆ Al kill groups hexyl, etc., to Asetokishi,

Cyclopropylcarbonyl O carboxymethyl, cyclopentylcarbonyl O carboxymethyl, cyclohexyl carbonyl O carboxymethyl cyclohexane, cyclopropylcarbonyl O key shell chill, C ₃ of cyclohexane and the like cyclopropylcarboxy two Ruokishi - ₆ consequent opening alkylcarbonyl O alkoxy C i — ₆ alkyl groups,

Methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, methoxycarbonyloxyl, ethoxycarbonyloxyl, n-propoxykaleponyloxymethyl, isopropoxycarbonyloxymethyl, n-butoxycarbonyloxymethyl, t C i- s alkoxycarboxy 2 ^^ ₆ alkyl group such as 1-butoxycarbonyloxymethyl

Phenylcarbonyloxy C — ₆ alkyl group such as benzoyloxymethyl, 2- (benzoyloxy) ethyl which may have a substituent on the benzene ring,

To methylthiomethyl, methylthioethyl, ethylthioethyl, ethylthiomethyl, ethyl propylthiomethyl, butylthiomethyl, etc. C i _ ₆ alkyl carbonylthio C ι _ ₆ alkyl group such as xyl,

Cyclopropylcarboxy two Ruchiomechiru, cyclopentyl carbonylation Ruchiomechiru, cyclo to Kishirukarubo two Ruchiomechiru, cyclopropylcarboxy two Ruchioechiru, C ₃ of cyclohexane and the like cyclopropylcarboxy two thio - ₆ cycloalkyl carbonylation thio C _ ₆ alkyl group,

Methoxycarbonylthiomethyl, ethoxycarbonylthiomethyl, methoxycarbonylthioethyl, ethoxycarbonylthioethyl, n-propoxycarbonylthiomethyl Chill, isopropoxycarbonyl carbonylation Ruchiomechiru, n- butoxycarbonyl two Ruchiomechiru, I- butoxycarbonyl two Ruchiomechiru such C - ₆ alkoxycarbonyl two thio C i _ ₆ § alkyl group

 A phenylcarbonylthio C-6 alkyl group such as benzoylthiomethyl and 2_ (benzoylthio) ethyl which may have a substituent on the benzene ring;

Benzyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, 2-cyclobenzyl, 4-methylbenzyl, 3-nitrobenzyl, 4-methoxybenzyl, 3,5-difluorobenzyl , 2- (4-black port phenyl) Echiru, 2- (4-Mechirufuweniru) Echiru, 2- (3, 4 one jib port Mofuweniru) E may Fuweniru may have a substituent chill like Ji _i-6 alkyl Represents a group.

1 ^ in the above formula is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl and its isomer, n-hexyl and its isomer, n- heptyl and its isomers, n- nonyl and its isomers, n- C i ₂ alkyl groups dodecyl,

Cyclopropyl, cyclobutyl, C ₃ _ ₆ cyclo alkyl group cyclohexyl, etc. cyclopentyl, cyclohexylene,

 Ci-6 haloa such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tripromomethyl, trichloroethyl, trifluoromethyl, pentafluoroethyl, etc. Ruquil group,

Main butoxy, ethoxy, Purobokishi, Isopurobokishi, butoxy, sec one butoxy, isobutoxy, t one-butoxy, etc. - ₆ alkoxy group,

Methylthio, Echiruchio, n- propylthio, isopropylthio, n- Puchiruchio, Isopuchiruchio, sec- Puchiruchio, C _1-6 alkylthio groups such as t- Puchiruchio, Mechiruamino, Echiruamino, n- Puropiruamino, isopropyl § amino, n- Bed Chiruamino, C alkylamino groups such as isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino, n-pentylamino,

 Di-C 1-6 alkylamino groups such as dimethylamino, dimethylamino, dipropylamino, dibutylamino, ethylisopropylamino, methylpropylamino, methylbutylamino, etc.

 A phenyl C 1-6 alkyl group which may have a substituent,

A phenyl 0 i- ₆ alkoxy group which may have a substituent, or

 Represents a phenyl group which may have a substituent.

Further, the substituted Ji also good Fuweniru - ₆ alkyl group Fuweniru C _1-6 § Examples of the alkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenyl-1-methylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl and the like. The phenyl which may have the substituent may be mentioned. Examples of C ₆ -alkoxy groups include benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenyl-1-methylethoxy, 1-phenylpropoxy, 2-phenylpropoxy, and 3-phenyl. And propoxy.

R ₂ is methyl, ethyl, n-propyl, isopropyl, n-butyl, isoptyl, sec-butyl, t-butyl, n-pentyl and its isomer, n-hexyl and its isomer, n-heptyl and It represents an isomer thereof, n-nonyl and its isomer, a Ci- ₁₂ alkyl group such as n-dodecyl, or a phenyl group which may have a substituent.

The substituent of the Fuweniru group which may have a substituent in the RR _2, full Tsu-containing, chlorine, bromine, halogen atom such as iodine, methyl, Echiru, n- propyl, iso-propyl, n- butyl, sec one heptyl, Isopuchiru, C! _ ₆ Al kill group such t- heptyl, chloromethyl, Furuoromechiru, bromomethyl, dichloromethyl, Jifuruo Romechiru, dibromomethyl, trichloromethyl, triflumizole Ruo Russia methyl, Toripuromome chill, trichloromethyl E chill, C 1-6 haloalkyl groups such as trifluoroethyl and pentafluoroethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy, etc. — ₆ alkoxy groups and the like.

 Is a cyano group, a nitro group,

 Halogen atoms such as fluorine, chlorine, bromine and iodine,

(^ _ ' ₆ alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and its isomers, n-hexyl and its isomers Group,

Cyclopropyl, Shikuropuchiru, cyclopentyl, cyclohexyl, C ₃ etc. - ₆ cyclo alkyl group,

Chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tripromethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, pentafluoro D- ₆ haloalkyl groups such as ethyl,

Ci- ₆ alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy,

C _1-6 haloalkoxy groups such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, etc. Represents

 γ is a dinitro group, a cyano group,

 Halogen atoms such as fluorine, chlorine, bromine and iodine,

 Methyl, ethyl, η-propyl, isopropyl, η-butyl, sec-butyl, isoptyl,! ; Alkyl groups such as -butyl,

Chloromethyl, Furuoromechiru, Promo methyl, dichloromethyl, Jifuruoromechi Le, dibromomethyl, trichloromethyl, triflumizole Ruo Russia methyl, tri promo, trichloromethyl E chill, torr full O Roe chill, C i _ ₆ such as penta full O Roe Chill Haloalkyl groups,

_6- alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, t-butoxy,

Ci-6 haloalkoxy groups such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, methylthio, ethylthioethyl, n-propylthio, isopropylthio, n-butylthio Ci- ₆ alkylthio groups such as, isobutylthio, sec-butylthio, t-butylthio, etc.

D- ₆ alkylsulfinyl groups such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, and butylsulfinyl;

C- ₆ alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, and butylsulfonyl;

Mechiruamino, Echiruamino, n- Puropiruamino, isopropyl § amino, n- Bed Chiruamino, Isopuchiruamino, sec - Puchiruamino, t-Puchiruamino, 1 over main Chirubuchiruamino, n- C WINCH ₆ alkylamino group such Penchiruamino,

Jimechiruamino, Jechiruamino, dipropylamino, Jibuchiruamino, Echirui isopropyl amino, methyl propyl § amino, di Ji _i-6 Al Kiruamino group such as a methyl Petit Rua Mino,

Ci- ₆ alkylcarbonyl groups such as methylcarbonyl, ethylcarbonyl, propylcarbonyl, and butylcarbonyl, or

 Represents a C 1-6 alkoxycarbonyl group such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl and t-butoxycarbonyl.

 Z represents a carbon atom or a nitrogen atom.

n represents 0 or an integer of 1 to 5; m represents 0 or an integer of 1 to 7; The compound of the present invention can be produced, for example, by the following method.

 (a) Method for producing compound (2) in which R is a hydrogen atom

(Expressed in the formula, X, Y, Z, m and η as defined above, 1 ^ is a halogen atom, - ₆ alkoxy group, Fuwenokishi group, 1-imidazolyl group, 1 one pyrazolyl group, p- Torr Ensuruhoniru A leaving group such as a methoxy group, a methanesulfonyloxy group or a trifluoromethanesulfonyl group.)

 That is, the compound represented by the formula (2) can be obtained by reacting the compound represented by the formula (3) with the compound represented by the formula (4) in the presence of a base.

 Bases used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and lithium carbonate, sodium methoxide, potassium t-butoxide, and magnesium. Metal alkoxides such as ethoxide, organic metals such as n-butyllithium and lithium diisopropylamide (LDA), metal hydrides such as sodium hydride and potassium hydride, organic bases such as triethylamine, diisopropylamine, pyridine, etc. Is mentioned. Solvents that can be used include N, N-dimethylformamide (DMF), dimethylsulfoxide (DMSO :), tetrahydrofuran (THF), acetonitrile, hexamethylphosphate amide (HMPA), benzene, Toluene, dichloromethane, chloroform, carbon tetrachloride and the like can be used. The reaction temperature is preferably in the temperature range from -78 ° C to the boiling point of the solvent used.

In addition, a phase transfer catalyst such as a quaternary amine and a base such as sodium hydroxide and hydroxylated diatom in a two-phase solvent of benzene, toluene, dichloromethane, chloroform, carbon tetrachloride, etc. and water. The compound represented by the formula (2) can be obtained by performing the reaction in a temperature range from −78 ° C. to the boiling point of the solvent used. The compound represented by the formula (2) exists as a keto-type or enol-type tautomer as shown in the following figure. In the compound of the present invention, the structure is mainly determined as an enol type in keto-type and enol-type tautomerism, but all of these two isomers are included in the scope of the present invention.

In addition, among the 2-cyanomethylthiazole compounds represented by the formula (3), the compound in which the 4-position is a naphthyl group having a substituent is a novel compound not described in the literature.

(b) A method for producing a compound in which R is a group other than a hydrogen atom

(Wherein, R, Rj, X, Y, Z, m, and n represent the same meaning as described above, and L ₂ represents a halogen atom, a P-toluenesulfonyloxy group, a methanesulfonyloxy group, or a trifluoromethanesulfonyl group. Represents a leaving group such as a xy group.

 By reacting the compound represented by the formula (2) with the compound represented by the formula (5) or (5 ′) in the presence of a base, the compound represented by the formula (1) or (Γ) is obtained. Can be

Bases used in this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and carbonated lime, sodium methoxide, potassium t-butoxide, and magnesium. Metal alkoxides such as ethoxide, n- Organic metals such as butyllithium and LDA; metal hydrides such as sodium hydride and potassium hydride; and organic bases such as triethylamine, diisopropylamine, and pyridine. In addition, as a solvent that can be used, DMF, DMSO, THF, lycetonitrile, HMPA, benzene, toluene, dichloromethane, chloroform, carbon tetrachloride, and the like can be used. The reaction temperature is preferably in the range from 178 ° C to the boiling point of the solvent used.

 In addition, a phase transfer catalyst such as a quaternary amine salt and a base such as sodium hydroxide or a hydroxylating bead are used in a two-phase solvent of benzene, toluene, dichloromethane, chloroform, carbon tetrachloride, etc. and water. The reaction can be performed in a temperature range from 8 ° C to the boiling point of the solvent used to obtain a compound represented by the formula (1) or (Γ).

 The compound of the present invention represented by the formula (1) has a stereoisomer as shown below, and depending on the reaction conditions and the purification method, any one of the two isomers may be used. In some cases, only the isomer is obtained, or as a mixture of two isomers. All of these isomers are included in the scope of the present invention.

After completion of the reaction, the desired product can be obtained by performing ordinary post-treatment. The structure of the compound of the present invention was determined from IR, NMR, MS and the like. Table 1 shows typical examples of the compounds of the present invention that can be produced as described above. The abbreviations in the table have the following meanings.

Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, P: phenyl, Hex: hexyl, Hep: heptyl, Oct: octyl, n: normal, i: iso, t : Tertiary, c: Shik π οτ

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Table 1 (continued)

91

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890 Od / d :) d 660 880 / ZO OAV

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890 Od / d :) d 660 880 / ZO OAV Table 1 (continued)

The following table illustrates all combinations of X n, Y and R represented by the above formulas 1 to 1 1 1 1 4,

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890l70 / Z0df / X3 <I 660880 / ZO OAV

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(^ ^) Halla I 喾

890 O Odf / ェ :) d 660 880 / ZO O / A o

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Table 1 (continued)

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Table 1 (continued)

Xn Y R

 2-F H R65

 2-C1 H R65

 2-Br H R65

 2 -Me H R65

2-CF ₃ H E65

2,6-F ₂ H R65

-C1-6-F H R65

 2-F H R66

 2-C1 H R66

 2-Br H R66

 2 -Me H R66

2-CF ₃ H R66

2,6-F ₂ H R66

-C1-6-F H R66

 2-F H R67

 2-C1 H R67

 2-Br H R67

 2 -Me H R67

2-CF ₃ H R67

2,6-F ₂ H R67

-C1-6-F H R67

 2-F H R68

 2-C1 H R68

 2-Br H R68

 2 -Me H R68

2-CF ₃ H R68

2,6-F ₂ H side

-C1-6-FH R68 (Pest control agent)

 The compound of the present invention is useful as an active ingredient of a pesticide, and particularly useful as an insecticide, an acaricide, a nematicide, a sanitary pest control agent, and a biofouling agent attached to water.

 When the compound of the present invention is actually applied, it can be used in a pure form without adding other components, and can be in the form of a general pesticide for use as a pesticide, for example, wettable powder, granule, It can be used in the form of powders, emulsions, aqueous solvents, suspensions, wettable powders and the like. When solid additives are used as additives and carriers, mineral powder such as soybean grains, vegetable powders such as flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, etc., and benzoin Organic and inorganic compounds such as acid soda, urea and sodium sulfate are used. For liquid dosage forms, kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, methylisobutyl ketone, mineral oil , Vegetable oil, water, etc. can be used as the solvent.

 In order to obtain a uniform and stable form in these preparations, a surfactant may be added if necessary. Although there is no particular limitation on the surfactant, for example, alkyl ether to which polyoxyethylene is added, higher fatty acid ester to which polyoxyethylene is added, sorbitan higher fatty acid ester to which polyoxyethylene is added, and polyoxyethylene are added Non-ionic surfactants such as tristyryl ethers, etc., sulfates of alkyl phenyl ethers to which polyoxyethylene is added, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfones And a formaldehyde condensate of alkyl naphthalene sulfonate, a copolymer of isobutylene-maleic anhydride, and the like.

 The amount of the active ingredient in the preparation is preferably from 0.01 to 90% by weight, particularly preferably from 0.05 to 85% by weight. The wettable powders, emulsions, suspensions, aqueous solvents, granular wettable powders and the like thus obtained are diluted to a predetermined concentration with water to obtain solutions, suspensions or emulsions, and powders and granules. Is applied directly to plants or soil.

It goes without saying that the compound of the present invention is effective alone, but it can also be used in combination with one or more of various fungicides, pesticides or synergists.

 Representative examples of fungicides, insecticides, acaricides, and plant growth regulators that can be used by mixing with the compound of the present invention are shown below.

 Fungicide:

Kyabtan, Forpet, Thiuram, Ziram, Zineb, Maneb, Mancozeb, Propineb, Polycarbamate, Chlorotatin, Kinto Isen, Kyaptahor, Prodione, Procymidone, Vinclozolin, Fluoroymid, Thymoxanil, Mepronil, Flutolanil, Pencyclon, Oxycarboxin, Josetyl aluminum, Propamocarb, Triadimefon, Triadimenol, Propiconazole, Diclobutrazol, Vitertanol, Hexaconazole, microbutanil, flusilazole, etaconazole, fluotrimazole, flutriafene, penconazole, diniconazole, cyproconazoles, finarimol, triflumizol, puclochloraz, imazalil, difurazoate, tridemorph, fen Propimorph, Trifolin, Petiobate, Pyrifinox, Anilazine, Polyoxin, Metalaxyl, Oxazixyl, Laxyl, isoprothiolane, probenazole, pyronitrile, blasticidin s, kasugamycin, noridamycin, dihydrostreptomycin sulfate, benomyl, carbendazim, thiophanate methyl, himexazole, basic copper chloride, basic sulfate Copper, Funtin acetate,

 Triphenyltin hydroxide, diethophane carb, metasulfo carb, quinomethionate, pinapacryl, lecithin, baking soda, dithianon, dinocap, phenaminosulf, dichromemidine, guazatine, dozine, IBP, edifenphos, mepanipyrim, fulemido, triclamidone Metasulfocarp, fluazinam, etoquinolak, dimethozolef, pyroquilon, tectophthalam, fusaride, phenazine oxide, thia bendazol, tricyclazol, vinclozolin, simoxanil, cyclobutanil, guazatine, propamocarplic acid hydrochloride, oxo

 Pest control agent:

Organophosphorus and carbamate pesticides:

 Fenthion, phenitrothion, diazinon, chlorpyrifos, ESP, bamidothion, pentoate, dimethate, formothione, marathon, trichlorfon, thiomethone, phosmet, dichlorvos, acephate, EPBP, methylthione, methylthiophene, thiophene, methylthiophene Cyanophos, isoxathion, pyridafenthion, hosalon, methidathion, sulprophos, chlorfenbinphos, tetrachlorovinphos, dimethylvinphos, propaphos, isophanphos, ethylthiomethone, profinophos, pyraclophos, monocrotophomethol, azidinfomethyl, carbodicarbometyl , Carbosulfan, Benfracarb, Fraciocal , Proboxil, BPMC, MTMC, MICPC, Kyvalyl, Pirimicarb, Etiophankalp, Phanoxycarp, etc.

Pyrethroid insecticides:

Permethrin, cypermethrin, deltamethrin, humvalerate, fumpro /, ° trin, pyrethrin, allesulin, tetramethrin, resmethrin, dimethrin, Propasulin, phenotrin, protoline, fluvalinate, cyflutrin, cyhalotrin, flucitrinate, etofenprox, cycloprotrin, tralomethrin, silafluofen, aclinatrin.

Benzoylurea and other insecticides:

 Difluvenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyphen, methoprene, benzepin, diafentiuron, imidacloprid, two Tembiram, acetamiprid, cartap, thiocyclam, bensultap, chlorfenapyr, emamectin benzoate, tebufenozide, fipronil, nicotine sulfate, rotenone, metaaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic virus.

Nematicide:

 Fenamiphos, phosthiazetate, etc.

Acaricide:

 Kulubenzylate, phenisobromolate, dicophor, amitraz, BPPS, benzomate, hexthiazox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetradihon, avermectin, milbemectin, clofentezine, cihexatin, pyridaben , Piromoximate, tebufenpyrad, pyrimidif [iota] ne, pentochalp, dienochlor, ethoxazole, halfenprox, acequinosyl, bifenazate, etc.

Plant growth regulator:

 Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.

 The compound of the present invention can be used for controlling agricultural pests, sanitary pests, storage pests, clothing pests, house pests, and the like, and has an adulticidal, nymphalidal, larvicidal, and ovicidal action. The following are typical examples.

 Lepidopteran insect pests, for example, Hasmonyoto, Totoga, Tamanayaga, Aomushi, Yumanana Ginpiba, Konaga, Chiyanokokakumonhamaki, Chiyamahamaki, Momomoshinga, Pear Himeshingui, Mikanhamoguriga, Chinohogasiga, Nikkomoga Kobu nomeiga, Kokuchi Pian corn borer, Amerikashiro hen, Sujimadarameiga, Heliotis, Helicoverpa, Agrotis, Iga, Codlinga, Peta mimushi, etc.

Hemiptera pests, such as peach aphids, peter aphids, mosquito aphids, wheat leaf aphids, scorpion bugs, stag beetles, Aphids, stag beetles, onyx whiteflies, tobacco whiteflies, pear lice, slime beetles, squirrels, squirrels, stomachs, tsumaga, etc.

 Coleopteran pests, for example, Lepidoptera, beetles, beetles, colorado beetles, rice worms, beetles, beetles, azuki beetles, beetle beetles, lycopodium, diablotica, tobacco beetle, beetle, beetles Diptera insect pests, such as Kokunusuto, P. japonicus, etc. Power etc.

 Hymenoptera pests, for example, Thrips palmi Karny, Thrips palmi, etc., Hymenoptera, pests, for example, Diplomatidae, Rhododendron wasp, etc. , Black cockroaches, etc.

 Isoptera pests, for example, house termites, japonicus termites,

 Lepidopteran insects, for example, flea flea, louse pests, for example, human louse, etc. Mites, for example, Namihadani, Nisenamihadani, Kanzahadani, Citrus spider mite, Apple spider mite, Citrus amphitheater, Apple savidani, Chiyano mite, Breviparpas Epotetranicus spp., Robin's mite, Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides farinae, Dermatophagoides farinae, etc.

 Plant-parasitic nematodes, for example, sweet potatoes, soybean cysts, soybean cysts, rice singers, pine moss, etc.

 Pests that are preferably applied include lepidopteran, hemiptera, coleopteran, throat and pests, and particularly preferably lepidopteran, pests and hempoids. In addition, in recent years, many insect pests such as Japanese moth, pests, leafhoppers, aphids, and asters have developed resistance to organophosphates, carbamates, and acaricides, and the lack of efficacy of these drugs has been addressed. Therefore, there is a need for a drug that is effective against insects and mites that are resistant to strains. The compound of the present invention is an agent having an excellent insecticidal and acaricidal effect against insects that are resistant not only to susceptible strains but also to organic phosphorus, carbamate, and pyrethroid-resistant strains, and to miticide-resistant strains. .

 The compound of the present invention has low phytotoxicity, low toxicity to fish and warm-blooded animals, and is a highly safe drug.

Further, the compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to aquatic organisms such as ship bottoms and fish nets. 【Example】

 Next, the present invention will be described in more detail with reference to examples.

 Example 1

 Preparation of 2'-chloro-3-hydroxy-1 2- [4- (1-naphthyl) thiazol-2-yl] nitrile monocinnamate (Compound No. 2-7)

Dissolve 0.8 g of 2-cyanomethyl-4- (1-naphthyl) thiazole in 15 mL of toluene, cool on ice, 0.65 g of tritylamine, 20 mg of 4-dimethylaminopyridine and 2-benzoyl chloride 1. After adding 3 g, the mixture was heated under reflux for 3 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate and saturated saline were added, and the organic layer was concentrated under reduced pressure to obtain an oil. The oil obtained here was dissolved in ethanol (19 mL), 10% aqueous sodium hydroxide solution (2.6 mL) was added under ice cooling, and the mixture was allowed to stand at room temperature overnight. The reaction solution was concentrated under reduced pressure, the obtained residue was dissolved in water, acidified by adding dilute hydrochloric acid, and then ethyl acetate was added. The residue obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography (developing solvent; 1: 4 ethyl acetate / n-hexane) to obtain 1.05 g of the desired compound as amorphous. Yield 84.1% Example 2

 Preparation of 2- [4- (1-naphthyl) thiazol-2-yl] bivaloyloxy-nitrile cinnamate (Compound No. 2-1)

2 '-Black mouth 3-Hydroxy 2-[4- (1-naphthyl) thiazolu-2-yl]-0.25 g of nitrile cinnamate dissolved in 10 ml of THF, cooled on ice, and triethyla Add 0.1 g of min and 0.1 g of bivaloyl chloride sequentially, bring to room temperature, and leave did. The precipitated salt was filtered, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (developing solvent; 1: 8 ethyl acetate, Zn hexane) to obtain 0.24 g of the desired compound as an amorphous solid. . Yield: 79.2% Table 2 shows the structural formula and physical constants of the compound of the present invention produced as described above.

Table 2

* [1: melting point ° C tf

890 OdfA d 660 880/10 OAV Next, some examples of the composition of the present invention will be described. However, the additives and the addition ratio are not limited to these examples, and can be changed in a wide range. The parts in the preparation examples are parts by weight. Formulation Example 1 wettable powder

 Compound of the present invention 40 parts

 Clay 4 8 parts

 Dioctyl sulfosuccinate sodium salt 4 parts

 Lignin sulfonic acid sodium salt 8 parts

If the above are uniformly mixed and finely pulverized, a wettable powder with an active ingredient of 40% is obtained. Formulation Example 2 Emulsion

 Compound of the present invention 10 parts

 Solbesso 2 0 0 5 3 parts

 Hexanone 2 6 parts

 Dodecylbenzenesulfonic acid calcium salt 1 part

 Polyoxyethylene alkylaryl ether 10 parts

 By mixing and dissolving the above, an emulsion containing 10% of the active ingredient is obtained. Formulation Example 3 Powder

 Compound of the present invention 10 parts

 Clay 90 parts

 If the above are uniformly mixed and finely pulverized, a powder containing 10% of the active ingredient is obtained. Formulation Example 4 Granules

 5 parts of the compound of the present invention

 Clay 7 3 parts

 Bentonite 20 parts

 Dioctyl sulfosuccinate sodium salt

 1 copy

 Potassium phosphate 1 part

The above is well pulverized and mixed, water is added and kneaded well, and the mixture is granulated and dried to obtain granules having an active ingredient of 5%. Formulation Example 5 Suspension

 Compound of the present invention 10 parts

 Polyoxyethylene alkylaryl ether 4 parts

 Sodium polycarboxylate 2 parts

 Glycerin 10 parts

 Xanthan gum 0.2 parts

 Water 73.8 parts

 The above ingredients are mixed and wet-pulverized to a particle size of 3 microns or less to obtain a 10% active ingredient suspension. Formulation Example 6 Granule wettable powder

 Compound of the present invention 40 parts

 Clay 36 parts

 Potassium chloride 10 parts

 Alkylbenzenesulfonic acid sodium salt 1 part

 Lignin sulfonic acid sodium salt 8 parts

 Alkylbenzenesulfonic acid sodium salt

 Mix at least 5 parts of formaldehyde condensate, pulverize finely, add an appropriate amount of water, and knead the mixture to form a clay. If granulated and dried, the active ingredient is 40%. To obtain a wettable powder. Industrial applicability:

 Examples in which the composition of the present invention obtained as described above is applied as a pesticide are shown below. Test Example 1 Efficacy against tabular beetle

 Germination seeds sown in three-size bowls, 10 days old, were inoculated with adult Aphid aphids. One day later, the adult was removed, and a drug solution diluted with water was sprayed on the cucumber parasitized by the born nymphs according to the formulation of the emulsion described in Formulation Example 2 of the drug so that the compound concentration became 125 ppm. did. They were placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65%, and after 5 days, they were examined for life and death, and the insecticidal rates were determined. The test is in duplicate. As a result, the following compounds showed an insecticidal rate of 100%. The compound numbers correspond to those in Table 2.

2—1, 2—2, 2-3, 2—13, 2—14, 2—15, 2—16, 2—17, 2-18, 2-19, 2-20, 2-21, 2 -23, 2-24, 2- 25, 2 -2 7, 2-28, 2 -29, 2 -31, 2-32, 2 -33, 2 -34, 2- 35, 2 -36, 2-37

 The insecticidal rate of Pirimicarb used as a control was 9%. Test example 2 Efficacy against aphalt

 According to the formulation of wettable powder shown in Formulation Example 1 of the above drug, the compound was diluted with water so that the compound concentration became 125 ppm. Corn leaves were immersed in the solution for 30 seconds, air-dried, placed in a petri dish covered with filter paper, and inoculated with 10 second instar larvae. They were covered with a glass lid and placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65%. The test is in duplicate.

As a result, the following compounds showed an insecticidal rate of 100%. The compound numbers correspond to those in Table 2.

 2-1, 1, 2, 2, 2-3, 2, 13, 2-14, 2-15, 2-16, 2, 17, 2-18, 2-19, 2, 22, 2-23, 2- 25, 2-27, 2-28, 2-29, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38

 The insecticidal rate of chlordimeform used as a control was 40%. Test Example 3 Efficacy against Conaga

 According to the formulation of the wettable powder described in Formulation Example 1 of the above drug, the compound was diluted with water so that the compound concentration became 125 ppm. Cabbage leaves were immersed in the solution for 30 seconds, air-dried, placed in a petri dish covered with filter paper, and inoculated with ten second instar larvae using a small brush. They were covered with a glass lid and placed in a thermostatic chamber at a temperature of 25 ° C and a humidity of 65%. After 5 days, the insecticidal rate was examined. The test is in duplicate.

As a result, the following compounds showed an insecticidal rate of 100%. The compound numbers correspond to those in Table 2.

 2-3, 2- 13, 2- 14, 2-15, 2-16, 2- 17, 2-30, 2-3 2, 2-33, 2-34, 2-35, 2-36

 The control rate of chlordimeform was 0%.

Claims

Claim formula (1)

 [1]

[Wherein, R is a hydrogen atom, a ₆ alkyl group, a group represented by the formula CORi, a group represented by the formula CSRi, or a group represented by S 0 ₂ R ₂ , a C- ₆ alkoxy C alkyl group, - ₆ alkylcarbonyl O alkoxy C alkyl group, C ₃ - ₆ cycloalkyl carbonylation Ruoki shea alkyl group, C -s alkoxycarbonyl two Ruokishi Ji ₆ alkyl group which may have a substituent Fuenirukarubo two Ruokishi Ji ₆ alkyl group , C alkylthio C _i-6 alkyl group, C alkyl carbonylation thio C _ ₆ alkyl group, C ₃ _ _s cycloalkyl carbonylation Lucio c ₆ alkyl group, C WINCH ₆ alkoxycarbonyl two thio C alkyl group, have a substituent A carbonylcarbonylthio C i- ₆ alkyl group which may be substituted, a phenyl C ^ 6 alkyl group which may have a substituent,

Is C i_ ₁₂ alkyl group, C ₃ _ ₆ cycloalkyl group, _d-6 haloalkyl group, d one

₆ alkoxy, Ci-s alkylthio group, C _i-6 alkylamino group, current affairs ₆ alkylamino group which may have a substituent Fuweniru C alkyl group, an optionally substituted phenyl C - ₆ Represents an alkoxy group, a phenyl group which may have a substituent,

R ₂ represents a C i _i ₂ alkyl group or an optionally substituted phenyl group;

Represents Shiano group, a nitro group, a halogen atom, Ci-s alkyl group, C ₃ _ ₆ a cycloalkyl group, C ₆ haloalkyl group, C i one ₆ alkoxy group, a C WINCH ₆ haloalkoxy group, Y is nitro Group, cyano group, halogen atom, Ci-e alkyl group, Ci-e; haloalkyl group, Ci- ₆ alkoxy group, Ci-6 haloalkoxy group, alkylthio group, —6alkylsulfinyl group, C alkylsulfonyl group, represents C alkylamino group, di-C i_ ₆ alkylamino group, C i_ ₆ alkylcarbonyl group, a C i_ ₆ alkoxycarbonyl group,

 z represents a carbon atom or a nitrogen atom,

 m represents an integer from 0 to 7,

n represents an integer of 0 to 5. ] The compound represented by these.

2. Equation [1]

 [1]

[Wherein, R, X, Y, Z, m and η have the same meanings as in claim 1.] ]

A pesticidal composition comprising, as an active ingredient, one or more compounds represented by the formula (I) or a salt thereof.