KR20020059648A - Novel compounds having cyano and insecticides and miticides - Google Patents

Abstract

Compounds represented by the general formula (1), methods for preparing the same, and insecticides and acaricides containing the compounds or salts thereof as active ingredients:

[Formula 1]

Wherein A represents one selected from the groups represented by A1 to A12; B represents a phenyl substituted by W or a heterocyclic group substituted by W; R is hydrogen, C _1-6 alkyl, COR ₁ , CSR ₁ , SO ₂ R ₂ , C _1-6 alkylcarbonyloxy (C _1-6 alkyl), C _3-6 cycloalkylcarbonyloxy (C _1-6 alkyl) or optionally substituted phenylcarbonyloxy ( C _1-6 alkyl).

Description

Novel compounds and cysticides having cyano groups {NOVEL COMPOUNDS HAVING CYANO AND INSECTICIDES AND MITICIDES}

To date, various insecticides and acaricides have been used for plant protection for controlling harmful insects and mites in agricultural crop production. However, due to the degradation of plant protection chemicals in their activities and the emergence of lines of insects and mites that are resistant to these insecticides and acaricides, their use for plant protection has been limited. In addition, many insecticides and acaricides tend to cause phytotoxicity to crops or are toxic to humans and animals. As a result, although many insecticides and acaricides for plant protection use have been developed and used, most of them are not satisfactory in view of the above-mentioned defects. Therefore, there is still a strong demand for the provision of pesticides and acaricides for the purpose of plant protection, which can solve the above-mentioned deficiencies and can be used in a safe manner.

Acrylonitrile compounds similar to the compounds according to the invention are disclosed, for example, in EP 189960, WO 97/40009, WO 98/42683, WO 98/35935, and WO 99/44993.

In addition, in Table I-d of WO 98/35935, a compound represented by the following formula is disclosed. However, in these disclosures, there is no description that any of the disclosed compounds had either pesticidal activity or acaricide activity.

The present invention relates to a novel compound, to a method for producing the compound, and to an insecticide and acaricide containing the compound.

It is an object of the present invention to be a major component of insecticides and acaricides for plant protection, to be advantageously synthesized on an industrial scale, to be used with definite pesticide and acaricide activity, and to be safe for humans, animals and crops. It is to provide a novel compound that can be.

1. According to a first aspect of the invention, there is provided a novel compound represented by the following formula (1):

Wherein A is selected from the group consisting of the groups represented by the following A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11 and A12:

Wherein X ₁ , X ₂ , X ₃ and X ₄ each independently represent hydrogen, halogen, C _1-6 alkyl or C _1-6 haloalkyl;

X ₅ represents hydrogen, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 haloalkenyl or optionally substituted phenyl C _1-6 alkyl;

X ₆ and X ₇ each independently represent C _1-6 alkyl, or X ₆ and X ₇ together may form a 5-8 membered ring;

Y is a cyano, C _1-6 alkyl, C _3-6 cycloalkyl, phenyl which benzene ring may be substituted with C _1-6 alkyl, G _1, G ₁ as optionally substituted optionally substituted with phenyl phenoxy, G ₁ when, with a benzene ring optionally substituted by phenoxy C _1-6 alkyl, G _1, which may be substituted by G ₁ phenylthio, G ₁ with an optionally substituted phenylthio C _1-6 alkyl, phenyl optionally substituted with G ₁ sulfinyl, benzene ring is phenyl, which is optionally substituted phenylsulfonyl, benzene ring, phenyl- sulfinyl C _1-6 alkyl, G _1, which may be substituted by G ₁ may be substituted with G _1-sulfonyl C _1-6 alkyl , optionally substituted with G ₁ is not Reno, a benzene ring which is optionally substituted by a thienyl, thiophene ring in Reno C _1-6 alkyl, G ₁ is not optionally substituted by G ₁ may be substituted with G _1-thienyl C _1-6 alkyl, pyridyl optionally substituted with G ₁ , and pyridyl C _1-6 alkyl wherein the pyridine ring may be substituted with G ₁ Represents one group;

Z represents oxygen, sulfur, or nitrogen substituted with hydrogen or C _1-6 alkyl;

G ₁ is nitro, cyano, halogen, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-8 cycloalkyl, C _1-6 haloalkyl, C _2-6 haloal Kenyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _2-6 alkenyloxy, C _2-6 haloalkenyloxy, C _2-6 alkynyloxy, C _1-6 alkylthio, C _{1- 6} alkylsulfinyl, C _1-6 alkylsulfonyl, C _1-6 alkylamino, di - (C _1-6 alkyl) amino, tri - (C _1-6 alkyl) silyl, C _1-6 alkoxy C _{1- 6} alkyl, C _1-6 alkylthio C _1-6 alkyl, C _1-6 alkylsulfinyl C _1-6 alkyl, C _1-6 alkylsulfonyl C _1-6 alkyl, C _1-6 alkylcarbonyl, C _1-6 alkoxycarbonyl, benzene ring is phenyl C _1-6 alkoxy group, a thiophene ring is phenyl C _1-6 alkyl, a benzene ring which may be optionally substituted with G ₂ is substituted by G ₂ are optionally substituted with G ₃ thienyl, the pyridine ring is optionally substituted pyridyloxy, optionally substituted phenyl, or G ₄ represents an optionally substituted phenoxy with a G ₄ to the pyridyl, G _2, which may be substituted with G ₂ which may;

G ₂ represents C _1-6 alkyl, halogen, C _1-6 haloalkyl or C _1-6 haloalkoxy;

G ₃ represents C _1-6 alkyl or halogen;

G ₄ is nitro, cyano, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _1-6 alkylthio, C _1-6 alkylsulfinyl , C _1-6 alkylsulfonyl, C _1-6 alkylamino, di- (C _1-6 alkyl) amino, C _1-6 alkylcarbonyl or C _1-6 alkoxycarbonyl);

B represents phenyl substituted with W or heterocyclic group substituted with W

Where W is nitro, cyano, halogen, C _1-6 alkyl, C _3-8 cycloalkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _1-6 alkyl alkylthio, C _1-6 alkylsulfinyl, C _1-6 alkylsulfonyl, C _1-6 alkylamino, di - (C _1-6 alkyl) amino, C _1-6 alkylcarbonyl, C _1-6 alkoxycarbonyl carbonyl, optionally represent an optionally substituted phenoxy or a phenyl substituted by G ₅ G _5,

Wherein G ₅ is nitro, cyano, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _1-6 alkylthio, C _1-6 alkyl Sulfinyl, C _1-6 alkylsulfonyl, C _1-6 alkylamino, di- (C _1-6 alkyl) amino, C _1-6 alkylcarbonyl or C _1-6 alkoxycarbonyl;

Heterocyclic groups substituted with W are triazolyl, thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyrazolyl, imidazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, thienyl, furyl, pyrrolyl , Any one group selected from the group consisting of pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl;

R is hydrogen, C _1-6 alkyl, a group represented by formula COR ₁ , a group represented by formula CSR ₁ , a group represented by formula SO ₂ R ₂ , C _1-6 alkylcarbonyloxy C _1-6 alkyl, C _3-6 cycloalkylcarbonyloxy C _1-6 alkyl or optionally substituted phenylcarbonyloxy C _1-6 alkyl

Wherein R ₁ is C _1-12 alkyl, C _3-6 cycloalkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 alkylthio, C _1-6 alkylamino, di- (C _1-6 alkyl) amino, optionally substituted phenyl C _1-6 alkyl, optionally substituted phenyl C _1-6 alkoxy or optionally substituted phenyl, R ₂ represents C _1-12 alkyl or optionally substituted phenyl) );

However, B is either phenyl substituted with W or pyridyl substituted with W, R is hydrogen, C _1-6 alkyl, a group represented by formula COR ₁ , a group represented by formula CSR ₁ or a formula SO ₂ R _When any of the groups represented by ₂ are not benzyl substituted with G ₁ }.

2. According to a second aspect of the present invention, there is provided a method for preparing a compound represented by the following formula (2), wherein the compound is prepared by reacting the compound of formula (3) with the compound of formula (4) in the presence of a base. A manufacturing method is provided:

(Wherein A and B are as defined in 1 above),

(Wherein A is as defined above),

(Wherein B is as defined above and L is a leaving group).

3. In the third aspect of the present invention, the method for preparing a compound represented by Chemical Formula 2 described above, wherein the compound is prepared by reacting the compound represented by the following Chemical Formula 5 with the compound represented by the following Chemical Formula 6. A manufacturing method is provided, in which:

(Wherein B is as defined above),

A-L '

(Wherein A is as defined in 2 above and L 'is a leaving group).

4. In a fourth aspect of the present invention, there is provided an insecticide / caricide which contains a compound represented by the formula (1) or a salt thereof as an active ingredient.

[Embodiment for Carrying Out the Invention]

In Chemical Formula 1 described above,

A is any one group represented by the formulas A1 to A12 described above;

Wherein X ₁ , X ₂ , X ₃ and X ₄ are each independently hydrogen,

Halogens such as fluorine, chlorine, bromine and iodine,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof, or

C _1-6 haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, Trifluoroethyl and pentafluoroethyl;

X ₅ is hydrogen,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

C _2-6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2 -Propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hex Senyl, 3-hexenyl, 4-hexenyl and 5-hexenyl,

C _2-6 haloalkenyl, such as 3-chloro-2-propenyl, 4-chloro-2-butenyl, 4,4-dichloro-3-butenyl, 4,4-difluoro-3-butenyl And 3,3-dichloro-2-propenyl, or

Optionally substituted phenyl C _1-6 alkyl such as phenylmethyl, 1-phenylethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, (2-chlorophenyl) methyl, (4-methylphenyl) methyl, 3 -Nitrophenylmethyl, (4-methoxyphenyl) methyl, (3,5-difluorophenyl) methyl, 2- (4-chlorophenyl) ethyl, 2- (4-methylphenyl) ethyl and 2- (3, 4-dibromophenyl) ethyl;

X ₆ and X ₇ are each independently C _1-6 alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl and isomers thereof, and hexyl and Represent an isomer thereof, or

X ₆ and X ₇ may together form a 5-8 membered ring, such as optionally substituted cyclopentyl, optionally substituted cyclohexyl, optionally substituted cycloheptyl and optionally substituted cyclooctyl;

Y is cyano,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

C _3-8 cycloalkyl such as cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1-methylcyclohexyl And 4-methylcyclohexyl, or

The G ₁ optionally substituted phenyl C _1-6 alkyl, with G ₁ optionally substituted phenyl, optionally substituted in any city substituted phenoxy, optionally substituted phenoxy during the G ₁ C _1-6 alkyl, G ₁ to G ₁ phenylthio, G ₁ with an optionally substituted phenylthio C _1-6 alkyl, G ₁ by a phenyl optionally substituted alkylsulfinyl, optionally substituted phenyl C _1-6 alkyl sulfinyl, optionally substituted phenylsulfonyl with G ₁ to G ₁ sulfonyl, G ₁ with an optionally substituted phenylsulfonyl C _1-6 alkyl, G ₁ as an optionally substituted anilino, optionally substituted anilino by G ₁ C _1-6 alkyl, an optionally substituted 2-thienyl with G ₁ , G ₁ with an optionally substituted 3-thienyl, optionally substituted by G ₁ a thienyl C _1-6 alkyl, an optionally substituted 2-pyridyl, 3-pyridyl optionally substituted by G ₁ to G _1, G ₁ 4-pyridyl optionally substituted with pyridyl C _1-6 alkyl optionally substituted with G ₁ ,

Where G ₁ is nitro, cyano,

Halogens such as fluorine, chlorine, bromine and iodine,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

C _2-6 alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2 -Propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hex Senyl, 3-hexenyl, 4-hexenyl and 5-hexenyl,

C _2-6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3 -Butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl and 1,1 Dimethyl-2-butynyl,

Optionally substituted C _3-8 cycloalkyl such as cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl, cyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 1- Methylcyclohexyl and 4-methylcyclohexyl,

C _1-6 haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, Trifluoroethyl and pentafluoroethyl,

C _2-6 haloalkenyl, such as 3-chloro-2-propenyl, 4-chloro-2-butenyl, 4,4-dichloro-3-butenyl, 4,4-difluoro-3-butenyl And 3,3-dichloro-2-propenyl,

C _1-6 alkoxy such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy,

C _1-6 haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, 2,2,2-trifluoro Roethoxy and pentafluoroethoxy,

C _2-6 alkenyloxy such as allyloxy, 2-propenyloxy, 2-butenyloxy and 2-methyl-3-propenyloxy,

C _2-6 haloalkenyloxy, such as 3-chloro-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 4-chloro-2-butenyloxy, 4,4-dichloro-3- Butenyloxy and 4,4-difluoro-3-butenyloxy,

C _2-6 alkynyloxy, such as 2-propynyloxy, 2-butynyloxy and 1-methyl-2-propynyloxy,

C _1-6 alkylthios such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and t-butylthio,

C _1-6 alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl and butylsulfinyl,

C _1-6 alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl and butylsulfonyl,

C _1-6 alkylamino such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino and n- Pentylamino,

Di- (Ci_ ₆ alkyl) amino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino and methylpropylamino,

_Tri- (Ci_ ₆ alkyl) silyl such as trimethylsilyl,

C _1-6 alkoxy C _1-6 alkyl such as methoxymethyl, methoxyethyl, ethoxymethyl, propoxymethyl and butoxymethyl,

C _1-6 alkylthio C _1-6 alkyl such as methylthiomethyl, methylthioethyl, ethylthioethyl, ethylthiomethyl, propylthiomethyl and butylthiomethyl,

C _1-6 alkylsulfinyl C _1-6 alkyl such as methylsulfinylmethyl, methylsulfinylethyl, ethylsulfinylethyl, ethylsulfinylmethyl, propylsulfinylmethyl and butylsulfinylmethyl,

C _1-6 alkylsulfonyl C _1-6 alkyl, such as methylsulfonylmethyl, methylsulfonylethyl, ethylsulfonylethyl, ethylsulfonylmethyl, propylsulfonylmethyl and butylsulfonylmethyl,

C _1-6 alkylcarbonyl such as methylcarbonyl, ethylcarbonyl, propylcarbonyl and butylcarbonyl,

C _1-6 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl and t-butoxycarbonyl,

Optionally substituted phenyl C _1-6 alkyl, optionally substituted phenyl C _1-6 alkoxy, optionally substituted thienyl, optionally substituted pyridyl G ₂ to G ₃ to G ₂ to G _2, optionally substituted with G ₂ pyridyloxy, a phenyl or G ₄ is optionally substituted by G ₄ represents a city optionally substituted phenoxy;

Wherein G ₂ represents:

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

Halogens such as fluorine, chlorine, bromine and iodine,

C _1-6 haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, Trifluoroethyl and pentafluoroethyl, or

C _1-6 haloalkoxy such as chloromethoxy, fluoromethoxy, bromomethoxy, dichloromethoxy, difluoromethoxy, dibromomethoxy, trichloromethoxy, trifluoromethoxy, tribromomethoxy, 2, 2,2-trichloroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy and perfluoropropoxy;

G ₃ represents:

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof, or

Halogen such as fluorine, chlorine, bromine and iodine;

G ₄ represents:

Halogens such as fluorine, chlorine, bromine and iodine,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof, or

C _1-6 haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, 2,2, 2-trichloroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl,

C _1-6 alkoxy such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy,

C _1-6 haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy and 1,1-difluoroethoxy,

C _1-6 alkylthios such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and t-butylthio,

C _1-6 alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl and n-butylsulfinyl,

C _1-6 alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl and n-butylsulfonyl,

C _1-6 alkylamino such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino and n- Pentylamino,

Di- (Ci_ ₆ alkyl) amino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino and methylpropylamino,

C _1-6 alkylcarbonyl, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl and n-butylcarbonyl, or

C _1-6 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl and t-butoxycarbonyl;

Z represents nitrogen substituted with oxygen, sulfur, or hydrogen or C _1-6 alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and t-butyl;

B represents phenyl substituted with W or heterocyclic group substituted with W,

Where W is nitro, cyano,

Halogens such as fluorine, chlorine, bromine and iodine,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl and isomers thereof, and n-hexyl and isomers thereof,

C _3-6 cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl,

C _1-6 haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, 2,2, 2-trichloroethyl, 2,2,2-trifluoroethyl and pentafluoroethyl,

C _1-6 alkoxy such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy,

C _1-6 haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy and 1,1-difluoroethoxy,

C _1-6 alkylthios such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and t-butylthio,

C _1-6 alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl and butylsulfinyl,

C _1-6 alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl and n-butylsulfonyl,

C _1-6 alkylamino such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino and n- Pentylamino,

Di- (Ci_ ₆ alkyl) amino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino and methylpropylamino,

C _1-6 alkylcarbonyl, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl and n-butylcarbonyl, or

C _1-6 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl and t-butoxycarbonyl,

As a phenyl or optionally substituted with G ₅ G ₅ represents an optionally substituted phenoxy City,

Where G ₅ is nitro, cyano,

Halogens such as fluorine, chlorine, bromine and iodine,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or t-butyl,

C _1-6 haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, Trifluoroethyl and pentafluoroethyl,

C _1-6 alkoxy such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy,

C _1-6 haloalkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy and 1,1-difluoroethoxy,

C _1-6 alkylthios such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and t-butylthio,

C _1-6 alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, n-propylsulfinyl and butylsulfinyl,

C _1-6 alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl and butylsulfonyl,

C _1-6 alkylamino such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino and n- Pentylamino,

Di- (Ci_ ₆ alkyl) amino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino, methylpropylamino and methylbutylamino,

C _1-6 alkylcarbonyl, such as methylcarbonyl, ethylcarbonyl, propylcarbonyl and butylcarbonyl, or

C _1-6 alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl and t-butoxycarbonyl;

Heterocyclic groups substituted with W are preferably 5 or 6 membered heterocycles containing 1 to 4 atoms in nitrogen, oxygen or sulfur such as 2-furyl, 3-furyl, 2-thienyl, 3-thier Nil, pyrrole-2-yl, pyrrole-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isox Sazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl , Pyrazol-3-yl, pyrazol-4-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, 1,2,4-triazol-3-yl, 1 , 2,3-triazol-4-yl, tetrazole, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,3,4-oxa Diazol-2-yl, 1,3,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1 , 3,4-thiadiazol-3-yl, 1,3,4-thiadiazol-5-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 5-pyridyl, 3-pyri Dazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl And 2-pyrazinyl;

R is hydrogen,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, pentyl and isomers thereof, and hexyl and isomers thereof, represented by the formula COR ₁ Groups, groups represented by the formula CSR ₁ , groups represented by the formula SO ₂ R ₂ ,

C _1-6 alkylcarbonyloxy C _1-6 alkyl such as acetoxymethyl, pivaloyloxymethyl, heptanoyloxymethyl, acetoxyethyl and acetoxyhexyl,

C _3-6 cycloalkylcarbonyloxy C _1-6 alkyl such as cyclopropylcarbonyloxymethyl, cyclopentylcarbonyloxymethyl, cyclohexylcarbonyloxymethyl, cyclopropylcarbonyloxyethyl and cyclopropylcarbonyloxyhexane , or

Phenylcarbonyloxy C _1-6 alkyl such as benzoyloxymethyl and 2- (benzoyloxy) ethyl,

Wherein R ₁ is C _1-12 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl and isomers thereof, n-hexyl and its Isomers, n-heptyl and isomers thereof, n-nonyl and isomers thereof, and n-dodecyl and isomers thereof,

C _3-6 cycloalkyl, such as cyclopropyl, cyclobutyl and cyclopentyl,

C _1-6 haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, Trifluoroethyl and pentafluoroethyl,

C _1-6 alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and t-butoxy,

C _1-6 alkylthios such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio and t-butylthio,

C _1-6 alkylamino such as methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, t-butylamino, 1-methylbutylamino and n- Pentylamino,

Di- (Ci_ ₆ alkyl) amino, such as dimethylamino, diethylamino, dipropylamino, dibutylamino, ethylisopropylamino, methylpropylamino and methylbutylamino,

Optionally substituted phenyl C _1-6 alkyl,

Optionally substituted phenyl C _1-6 alkoxy, or

Optionally substituted phenyl; And

R ₂ is C _1-12 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and its isomers, n-nonyl and its isomers, and n-dodecyl and its isomers, or optionally substituted phenyl.

Examples of optionally substituted phenyl represented by R ₁ and R ₂ include:

Halogens such as fluorine, chlorine, bromine and iodine,

C _1-6 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or t-butyl,

C _1-6 haloalkyl, such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, Trifluoroethyl and pentafluoroethyl, and

C _1-6 alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy and t-butoxy.

Examples of phenyl C _1-6 alkyl in the above-exemplified C _1-6 alkyl is optionally substituted phenyl, benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenyl-1-methylethyl, 1-phenylpropyl, 2- Phenylpropyl, 3-phenylpropyl, and the like. Examples of phenyl C _1-6 alkoxy group exemplified above optionally substituted phenyl C _1-6 alkoxy is benzyloxy, 1-phenyl-ethoxy, 2-phenyl ethoxy, 1-phenyl-1-methylethoxy, 1-phenyl Propoxy, 2-phenylpropoxy, 3-phenylpropoxy and the like.

Compounds of the invention are prepared, for example, according to the process as described below.

(a) Process 1 for the preparation of a compound represented by formula (2) wherein R is hydrogen.

Wherein A and B are as defined above and L is a leaving group such as halogen, C _1-6 alkoxy, phenoxy, 1-imidazolyl, 1-pyrazolyl, p-toluenesulfonyloxy, (p -Methylphenylsulfonyloxy), methanesulfonyloxy (methylsulfonyloxy), and trifluoromethanesulfonyloxy (trifluoromethylsulfonyloxy).

In other words, the compound represented by the formula (2) is obtained by reacting the compound represented by the formula (3) with the compound represented by the formula (4) in the presence of a base.

Examples of bases to be used in the reaction include metal hydroxides such as sodium and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, organic metals such as n-butyl lithium and lithium diisopropylamide (LDA), metal hydrides, Such as sodium hydride and potassium hydride, and organic bases such as triethylamine, diisopropylethylamine and pyridine.

Examples of solvents usable in the reaction include N, N-dimethylformamide (DMF), N, N-dimethylacetamide, dimethylsulfoxide (DMSO), tetrahydrofuran (THF), acetonitrile, hexamethylphosphate amide ( HMPT), benzene, toluene, dichloromethane, chloroform and carbon tetrachloride. The reaction temperature for the reaction is preferably in the range of -78 ° C to the boiling point of the solvent used.

(b) Process 2: for the preparation of a compound represented by formula (2) wherein R is hydrogen

Wherein A and B are as defined above and L 'is a leaving group such as halogen, C _1-6 alkoxy, phenoxy, 1-imidazolyl, 1-pyrazolyl, p-toluenesulfonyloxy, methane Sulfonyloxy, trifluoromethanesulfonyl, phthalimide, and succinimide).

In other words, the compound represented by the formula (2) is a cyanoacetyl compound represented by the formula (5) in the presence or absence of a base, and any one of substituted alkyl halides, substituted benzyl halides, and substituted phenethyl halides (these All of which are readily represented by the formula (6).

Examples of bases used in the reaction include metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, organic metals such as n-butyl lithium and lithium diisopropylamide (LDA), metal hydrides Such as sodium hydride and potassium hydride, and organic bases such as triethylamine, diisopropylethylamine and pyridine.

Examples of solvents that can be used in the reaction include DMF, N, N-dimethylacetamide, DMSO, THF, acetonitrile, HMPT, benzene, toluene, dichloromethane, chloroform and carbon tetrachloride. The reaction temperature for the reaction is preferably in the range of -78 ° C to the boiling point of the solvent used.

The cyanoacetyl compound represented by the formula (5) used as starting material in the above reaction can be easily prepared according to the method described below, for example.

Wherein B is as defined above and L ″ represents halogen.

(c) Process 3: for the preparation of the compound represented by the formula (2) wherein R is hydrogen

Wherein A, B, L and L 'are as defined above and L' represents a leaving group such as halogen, p-toluenesulfonyloxy, methanesulfonyloxy, and trifluoromethanesulfonyloxy, R ₃ represents C _1-6 alkyl).

First, the compound represented by the formula (8) is prepared by applying the cyanoacetic acid ester represented by the formula (7) to the reaction with the compound represented by the formula (6) in the presence of a base.

There are two processes for carrying out the reaction. One process is carried out in a solvent such as DMF, DMSO, THF, acetonitrile or HMPT and in the presence of a base such as sodium hydride, potassium hydride or sodium carbonate. Other processes are in a two-layer solvent system consisting of water and any one selected from the group consisting of benzene, toluene, dichloromethane, chloroform and carbon tetrachloride, and the presence of a phase transfer catalyst such as quaternary amine, and a base such as sodium or potassium hydroxide The reaction is carried out at a reaction temperature under -78 ° C to the boiling point of the solvent used.

The compound represented by the formula (9) is prepared by reacting the obtained compound represented by the formula (8) with the compound represented by the formula (4) in the presence of a base.

The above mentioned reaction is carried out in a solvent such as DMF, DMSO, THF, acetonitrile, HMPT, benzene, toluene, dichloromethane, chloroform or carbon tetrachloride at a reaction temperature within the boiling range of the solvent used from -78 ° C and a base such as hydroxide It is carried out in the presence of sodium, potassium hydroxide, sodium carbonate, potassium carbonate, n-butyl lithium, lithium diisopropylamide (LDA), sodium hydride, potassium hydride, triethylamine, diisopropylethylamine or pyridine.

Thereafter, the obtained compound represented by the formula (9) is subjected to dealkoxycarbonylation to prepare a compound represented by the formula (2).

The reaction just mentioned above is carried out in a solvent such as water, methanol, ethanol, dimethoxyethane, dioxane, DMF, DMSO, benzene or toluene at a reaction temperature within the boiling point range of -78 ° C. to the solvent used, and an acid such as Sulfuric acid, hydrochloric acid, acetic acid or p-toluene sulfonic acid, and bases such as sodium hydroxide, sodium methoxide or triethylamine, and metal halides such as lithium chloride or calcium chloride.

It is noted that the compound represented by the formula (2) will be prepared in two forms of tautomers, ie, keto form and enol form, all of which are included in the compound defined in the second aspect of the present invention.

(d) a process for the preparation of compounds represented by formula (2) wherein R is a group other than hydrogen:

Wherein A, B and R are as defined above and L "is a leaving group such as halogen, C _1-6 alkoxy, phenoxy, 1-imidazolyl, 1-pyrazolyl, p-toluenesulfonyloxy Methanesulfonyloxy and trifluoromethanesulfonyloxy).

The compound represented by the formula (1) may be prepared by reacting the compound represented by the formula (10) with the compound represented by the formula (2) in the presence of a base.

Examples of bases used in the reaction include metal hydroxides such as sodium and potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, organometallic compounds such as N-butyl lithium and LDA, metal hydrides such as sodium hydride and hydrogenation Potassium and organic bases such as triethylamine, diisopropylethylamine or pyridine.

In addition, examples of the solvent used in the reaction include DMF, DMSO, THF, acetonitrile, HMPT, benzene, toluene, dichloromethane, chloroform and carbon tetrachloride. The reaction temperature for the reaction is preferably in the range of -78 ° C to the boiling point of the solvent used.

The target compound of the present invention represented by the formula (1) is prepared with its stereoisomer represented by the formula (1 ') shown below. Depending on the reaction conditions and the purification process, one of these isomers may optionally be obtained. Likewise, depending on the reaction conditions and the purification process, a mixture of these isomers can be obtained. All of these isomers are included in the compounds defined in the present invention.

After completing the reaction given above, the target compound can be obtained by subjecting the reaction product to a conventional post reaction procedure. The chemical structure of the obtained compound can be determined using IR, NMR, MS and the like.

Representative compounds for the compounds according to the invention, prepared as described above, are listed in Tables 1-3. Note that the abbreviated symbols in the table indicate the following meanings.

Me: methyl, Et: ethyl, Pr: propyl, Bu: butyl, Ph: phenyl, Hex: hexyl, n: normal, i: iso, t: tert (tertiary), c: cyclo

Combinations of B, R and Xn in all the compounds represented by the above formulas 1-1 to 1-96 are illustrated in the table below.

The combination of B and R in all the compounds represented by the said Formulas 2-1-2-58 is illustrated in the following table.

[Hazardous biocontrol agents]

The compounds according to the invention are useful for acting as active ingredients of biologically active agents, and are insecticides, acaricides, nematicides for plant protection, insecticides for hygienic purposes, and antifouling agents for aquatic organisms. Especially useful as Most preferably, the composition containing the compound of this invention is used as a pesticide and acaricide.

When applying the compounds of the present invention in a practical manner, the compounds may be applied in their form without addition of other ingredients. When the compounds of the present invention are applied for plant protection purposes, the compounds are prepared in conventional forms of formulations for plant protection applications such as wettable powders, granules, powders, emulsifiable concentrates, water soluble powders, suspension concentrates, flowable liquids and the like. Can be.

When preparing the compounds of the present invention in solid formulations, suitable additives and carriers may be incorporated with the compounds. Examples of additives and carriers include vegetable powders such as soy flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay, and organic and inorganic compounds such as sodium benzoate, urea and Forget-me-not. When preparing the compounds of the present invention in liquid formulations, suitable solvents are used to dissolve or disperse the compounds in liquid formulations. Examples of solvents used for liquid formulations include petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohols, acetone, methyl isobutyl ketone, mineral oils, Vegetable oils and water.

It is also possible to add surfactants to each formulation, if necessary, to impart uniformity and stability to the compounds in the formulations prepared. There are no limitations to the surfactants, and examples of the surfactants that may be added to the aforementioned formulations include nonionic surfactants such as polyoxyethylene added alkyl ethers, polyoxyethylene added higher fatty acid esters, polyoxyethylene added sorbitan higher Fatty acid esters and formaldehyde condensates of polyoxyethylene added tristyryl phenyl ethers, sulfate esters of polyoxyethylene added alkyl phenyl ethers, alkyl benzene sulfonates, polycarbonates, lignin sulfonates, alkyl naphthalene sulfonates, and Copolymers of isobutylene and maleic anhydride are included.

Typically, the content of active ingredient in each of the formulations listed above is preferably in the range of 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, relative to the weight of the formulation. Each of the prepared formulations, such as wettable powders, emulsifiable concentrates, suspension concentrates and flowable solutions, is diluted with water, prepared and controlled in suspension or emulsion to the desired concentration and applied to the crop. In formulations such as granule and powder formulations, the formulation itself is applied directly to the target crop or soil.

Of course, although the compounds according to the invention alone have sufficient pesticidal and acaricide activity, they may be used in combination with one or more of various forms of other plant protection chemicals, for example fungicides, pesticides, acaricides and synergists. have.

Hereinafter, representative examples of fungicides, insecticides, acaricides and plant growth regulators which can be used in combination with the compounds according to the present invention will be listed below.

disinfectant:

Captan, Folpet, Thiuram, Ziram, Zineb, Maneb, Mancozeb, Propineb, Polycarbamate Chlorothalonil, Quintozene, Quintozene, Captafol, Iprodione, Procymidone, Procymidone, Vinclozolin, Fluorimide, Cymoxanyl (Cymoxanil), Mepronil, Flutonil, Flutonil, Pencycuron, Oxycarboxine, Fosetyl aluminum, Propamocarb, Triadimefon Triadimefon, Triadimenol, Propicazole, Diclobutrazol, Bittertanol, Hexaconazol, Microbutanil, Flubutrazol Flusilazole, Etaconazole, Fluotrimazole, Flutrifen, Penconazole, Diconazole, Cyproconazole, Fenarimol, Triflumizole, Prochloraz, Imazalyl, Pepurazoate, Tree Tridmorph, Fenpropimorph, Triforine, Buthiobate, Pyrifenox, Anilazine, Polyoxins, Polyoxins, Metallaxyl (Metalaxyl), Oxadixyl, Furalaxyl, Isoprothiolane, Probenazole, Pyrrolenitrine, Blastocidin-S, Carca Sugamycin, Balidamycin, Dihydrostreptomycin Sulfate, Benomyl, Carbendazim, Thiophanate Methyl, Hymexazol, Basic Copper Chloride, Basic Copper Sulfate, Fentin Acetate, Triphenyltin Hydroxide, diethofencarb, metasulfocarb, quinomethionate, vinapacryl, lecithin, sodium bicarbonate, dithionone, dinocap ( Dinocap, Fenaminosulf, Diclomezine, GuazatineDodine, IBP, Edifenphos, Mepanipyrim, Ferimzone, Tree Trimidamide, Metasulfocarb, Fluazinam, Ethoquinolac, Dimetomorph, Pyroquilon, Tecloftalam , Phthalide, phenazine oxide, thiabazole, tricyclazole, vinclozolin, cymoxanil, cyclobutanil , Guaztine, propamocarb hydrochloride, oxolinic acid.

Pesticides and Fungicides:

Organophosphorus and carbamate insecticides: Penthion, Fenitrothion, Diazinon, Chlorpyrifos, ESP, Vamidothion, Fenthoate, Dimethoate, Formothion, Malathion, Trichlorfon, Thiometon, Phosmet, Dichlorvos, Acephate ), EPBP, methyl parathion, oxadimethone methyl, ethion, salition, cyanophos, isoxation, pyridafenthion, phosalone, methidion ( Methidathion, Sulprofos, Chlorfevinphos, Tetrachlorbinfos, Dimethylbinfos, Propaphos, Isofenfoss, Ethyl Thiomethone, Propenophos, Pyraclofos, Monocrotophos, Azinphos Methyl, Aldicarb ), Methomyl, Dithiocarb, Carbofuran, Carbosulfan, Benfuracarb, Furathiocarb, Propoxur ( Propoxur, BPMC, MTMC, MIPC, Carbaryl, Pyrimicarb, Ethiofencarb, Fenoxycarb, cartap, thiocyclam ), Bensultap and the like.

Pyrethroid insecticides: Permethrin, Cypermethrin. Deltamethrin, Fenvalerate, Fenpropathrin, Pyrethrin, Allethrin, Tetramethrin, Resmethrin, Dimethrin, Propartrin Fenothrin, Prothrin, Fluvalinate, Cyfluthrin, Cyhalothrin, Flucythrinate, Ethofenprox, Cyclopro Cycloprothrin, Tralomethrin, Silafluofen, Brofenprox, Acrinathrin and the like.

Benzoyl urea and other pesticides: Diflubenzuron, Chlorfluazuron, Hexaflumuron, Triplelumuron, Tetrabenzuron, Fulfenoxuron, Flucycloxuron ), Buprofezin, Pyriproxyfen, Methoprene, Benzoepin, Diafenthiuron, Imidacloprid, Fipronyl, Nicotine Microbial insecticides such as sulphate, rotenone, metaldehyde, machine oil, BT and insect pathogenic viruses.

Nematodes: Fenamiphos, Fosthiazate and the like.

Acaricides:

Chlorbenzilate, Penisobromolate, Dicopol, Amitraz, BPPS, Benzomate, Hexythiazox, Fenbutatin ) Oxide, Polynactin, Quinomethionate, CPCBS, Teteradifon, Avermectin, Milbemectin, Clofentezin, Sai Hexatin, Pyridaben, Penpyroxymate, Tebufenpyrad, Pyrimidifen, Fenothiocarb, Dienochlor, etc. .

Plant growth regulators: Gibberellins (eg, Gibberellin A3, Gibberellin A4, Gibberellin A7), IAA, NAA and the like.

The compounds according to the invention can be used for the control of harmful insects and mites that are prevalent in agricultural crops, hygienically problematic insects and mites, garment pests, and house pests. With respect to these harmful insects, the compounds of the present invention have insecticidal insects, larvae insecticides, insecticides and sallan activity. Representative examples of insects and mites in question are exemplified below.

Examples of insects of the tree species: buckthorn moth, cabbage chestnut moth, rounded moth, grass white butterfly, sugar beet leaf moth (Beet semi-looper), Chinese cabbage moth, Adoxophyes sp., Oriental tea tortrix ), Peach Core Moth, Peach Pure Moth, Tangerine Moth, Tea Leafroller, Apple Moth, Moth, Moth, Moth, Rice Leaf Moth, Rice Leaf Moth, Light Moth, American White Moth Allied moth, Heliothis sp., Helicobpa sp., Agrotis sp., Moth, Codling moth, Thyme moth.

Examples of banyan tree insects: peach aphids, cotton aphids, turnip aphids, millet rim aphids, sawtail antler, grass stink bugs, arrowworms, powdery beetles, greenhouse dusts, sweet potato powdery, pear tree pears, pear shields, and rice worms , Locusts, white locusts, cicadas etc.

Examples of vegetation insects: flea leaf beetle, gourd leaf beetle, Colorado potato leaf beetle, rice weevil, young rice weevil, red bean weevil, beetle, beetle, diabrotica (Diabrotica sp.) Sky Cow, Alligator, Agliotes sp., 28 Spotted Ladybug, Rice Thief, Cottonseed Weevil, etc.

Examples of double-flying insects: housefly, large blackfly (Calliphora lata), dungfly (Boettcherisca peregrina), melon fruit fly, tangerine fruit fly, Ursiaceae, rice leafminer, yellow fruit fly (Yellow drosophila) Flies (Stomoxys calcitrans), Encephalitis (Culex tritaeniarhynchus), Aedes aegypti, Anopheles hycanus, etc.

Examples of all-time insects include: Thrips palmi, Staphylococcus beetle, etc.

Examples of maximal insects: monomorium pharaonis, yellow harnet, cabbage sawfly, and the like.

Examples of direct-infestation insects: Asian locust, German wheels, foreign wheels, Japanese wheels, etc.

Examples of isotropic insects: ground termites in Taiwan, termites (Reticulitermes spetatus), etc.

Examples of silverback insects: human fleas, etc.

Examples of the two-headed insects: Lee et al.

Mites: spotted mites, spotted mites, mandarin and mites, tangerine mites, apple mites, tangerine mites, apple green mites, dust mites, Brevipalpus sp., Eotetranychus sp. Root mites, dust mites, desmatophagoides farinae, boophilus microplus, haemaphysallis bispinosa, and the like.

Examples of plant parasitic nematodes: sweet potato rootworm nematode, rootworm nematode, soybean cyst nematode, rice ear nematode, pine nematode, etc.

Among the harmful insects and mites exemplified above, the compounds of the present invention are preferably applied to control insects of the order of the tree, insects of the semi-entertainment, insects of the first order, insects of the whole order, and mites. In particular, the compounds of the present invention are most preferably applied to the control of insects, semi-historic insects and mites.

On the other hand, in recent years, many kinds of insects and mites such as Chinese cabbage moth, cicada larvae, locusts, aphids and mites have developed resistance to insecticides, carbamate insecticides and acaricides which are organic. In such a case, the insecticidal and acaricide activity of these insecticides and acaricides is lowered due to the occurrence of resistance problems. Thus, there is an increasing demand for new insecticides and acaricides that can act even on such resistant strains of insects and mites. The compound of the present invention is not only a line of insects and mites that can act against conventional insecticides and acaricides, but also the above-mentioned organic phosphorus insecticides, carbamate insecticides, pyrethroid insecticides, which have developed resistance to insects and mites in question And attention should be paid to the compounds of the present invention that they appear to have an excellent effect on the resistant strains of insects and mites that have developed resistance to many acaricides.

It can also be noted that the compounds of the present invention are highly safe, impart less phytotoxicity to crops, and are less toxic to fish and warm-blooded animals.

In addition, the compounds of the present invention can be used as antifouling agents for protecting marine and aquatic structures, such as the bottoms and fishing nets of ships, from aquatic organisms.

The present invention will now be described in detail by way of examples described below.

Example 1:

Preparation of γ-phenyl-α- (2-trifluoromethylbenzoyl) butyronitrile (Compound No. 10-1)

To 15 ml of a THF suspension containing 1.44 g of ethyl 2-trifluoromethylbenzoate and 1.39 g of potassium hydride (oil: 35%), 0.8 g of γ-phenylbutyronitrile was added dropwise and the solution was allowed to stand at room temperature for 1 hour. Was stirred. The reaction mixture was poured into aqueous saturated ammonium chloride and extracted with diethyl ether, which was washed with water and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent, ethyl acetate / n-hexane = 1/3) to give 1.74 g of the target compound. Yield: 99%.

Example 2:

Preparation of α- (2-phenylethyl) -β-pivaloyloxy-β- (2-trifluoromethylphenyl) acrylonitrile (Compound No. 4-1)

1.00 g of γ-phenyl-α- (2-trifluoromethylbenzoyl) butyronitrile is dissolved in 10 ml of THF, and 0.38 g of triethylamine and 0.46 g of pivaloyl chloride are continuously added to the solution in an ice bath. It was. Thereafter, the obtained mixture was stirred for 2 hours. The precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent, ethyl acetate / n-hexane = 1/5) to give 0.90 g of the target compound. Yield: 71%, Melting point: 82 ° C.

Example 3:

Preparation of α- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) carbonyl-γ- (4-chlorophenyl) butyronitrile (Compound No. 10-2)

1) Preparation of tert-Butyl-γ- (4-chlorophenyl) -α-cyanobutyrate:

3.00 g of 4-chlorophenethyl alcohol were dissolved in 45 mL of diethyl ether, and 0.51 g of 2,6-lutidine, 6.28 g of triphenylphosphine and 7.62 g of carbon tetrabromide were continuously added to the solution. The mixture was stirred overnight. The precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was suspended with n-hexane, filtered and concentrated under reduced pressure. The residue was taken up with hexane, which was washed with 5% aqueous hydrochloric acid and concentrated under reduced pressure to give 5.84 g of crude 4-chlorophenethylbromide.

5.84 g of crude 4-chlorophenethylbromide was dissolved in 20 ml of acetonitrile, and 1.62 g of cyanoacetic acid tert-butyl ester and 1.59 g of potassium carbonate were continuously added to the solution. The mixture was heated at reflux overnight. The precipitate was filtered off and the filtrate was concentrated under reduced pressure to give a residue, which was purified by chromatography on silica gel (developing solvent: eluent, ethyl acetate / n-hexane = 1/15) to give 1.70 g of the target compound. Yield: 63% (step 2).

2) Preparation of tert-butyl-α- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) carbonyl-γ- (4-chlorophenyl) -α-cyanobutyrate:

1.70 g of tert-butyl-γ- (4-chlorophenyl) -α-cyanobutyrate was dissolved in 30 mL of toluene, and 0.68 g of triethylamine, 0.20 g of 4-dimethylaminopyridine, and 5-chloro- were added to the solution. After 5 ml of a toluene solution of 1.80 g of 1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid chloride was continuously added in an ice bath, the mixture was refluxed for 2 hours. The precipitate was filtered off and the filtrate was concentrated under reduced pressure to give a residue, which was purified by chromatography on silica gel (eluent, ethyl acetate / n-hexane = 1/4) to give 2.23 g of the target compound. Yield 75%.

3) Preparation of α- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) carbonyl-γ- (4-chlorophenyl) butyronitrile

1.10 g of α-tert-butoxycarbonyl-α- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) carbonyl-γ- (4-chlorophenyl) butyronitrile It was dissolved in 10 ml of toluene, 0.10 g of p-toluenesulfonic acid monohydrate was added to the solution, and the mixture was heated under reflux for 2 hours. The mixture was concentrated under reduced pressure to give a residue, which was purified by chromatography on silica gel (eluent, ethyl acetate / n-hexane = 1/2) to give 0.69 g of the target compound.

Yield: 80%, Melting point: 75 to 76 ° C.

Example 4:

β- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -α- [2- (4-chlorophenyl) ethyl] -β-pivaloyloxyacrylonitrile (compound Preparation of numbers 4-2, 4-3)

9.28 g of α- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) carbonyl-γ- (4-chlorophenyl) butyronitrile is dissolved in 100 ml of THF, and the solution To this were added 3.19 g of triethylamine and 3.82 g of pivaloyl chloride successively, and the mixture was stirred at room temperature for 2 hours. The precipitate was filtered off and the filtrate was concentrated under reduced pressure to give a residue, which was purified by chromatography on silica gel (eluent, ethyl acetate / n-hexane = 1/4) to give the target compound (numbers 4-2 and 4). -3) was obtained 7.76 g and 0.05 g, respectively.

No. 4-2: yield, 69%, melting point, 85-87 degreeC.

No. 4-3: yield 0.4%, melting point, 101-102 degreeC.

Example 5:

of β- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -β-hydroxy-α- (2-phenylethenyl) acrylonitrile (Compound No. 5-54) Produce

0.8 g of 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid is dissolved in 10 ml of N, N-dimethylformamide, and 0.57 g of carbonyl bisimidazole is added to the solution. It was. After the mixture was stirred at room temperature for 1 hour, 0.5 g of cinnamil cyanide and then 0.14 g of sodium hydride (oily, 60%) were added to the mixture in an ice bath. After the mixture was further stirred at room temperature for 3 hours, the solution was poured into ice water and diluted hydrochloric acid was added to prepare an acidic solution. The solution was extracted with ethyl acetate and the organic layer was concentrated under reduced pressure to give a residue, which was purified by chromatography on silica gel (eluent, ethyl acetate / n-hexane = 1/2) to give 0.91 g of the target compound. Yield 74%.

Example 6:

β- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -α- (2-phenylethenyl) -β-pivaloyloxyacrylonitrile (Compound No. 5-1 Manufacturing

0.91 g of β- (5-chloro-1-methyl-3-trifluoromethylpyrazol-4-yl) -hydroxy-α- (2-phenylethenyl) acrylonitrile is dissolved in 10 ml of THF, Triethylamine and 0.40 g of pivaloyl chloride were continuously added to the solution in an ice bath. The mixture was stirred at rt for 2 h, then the precipitate was filtered off and the filtrate was concentrated under reduced pressure to give a residue. The residue was then purified by chromatography on silica gel (eluent, ethyl acetate / n-hexane = 1/4) to give 0.46 g of the target compound. Yield: 80%, Melting point: 80 to 82 캜.

Example 7:

Preparation of 1-methyl-3-trifluoromethyl-4- [4- (4-fluorophenyl) -4-oxo-2-cyanobutylyl] -5-chloropyrazole:

To 10 ml of a solution of 1.0 g of 1-methyl-3-trifluoromethyl-4-cyanoacetyl-5-chloropyrazole and 1.0 g of diisopropylethylamine in 10 ml of methylene chloride, 4-70 having a purity of 70% 1.3 g of (1-oxo-2-bromoethyl) fluorobenzene was added at 0 ° C. The mixture was stirred at room temperature for 18 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The obtained residue was purified by chromatography on silica gel (eluent, n-hexane / ethyl acetate = 1/1) to give 1-methyl-3-trifluoromethyl-4- [4- (4-fluorophenyl ) 1.0 g of oxo-2-cyanobutylyl] -5-chloropyrazole was obtained. Melting point: 179-181 degreeC.

Example 8:

1-methyl-3-trifluoromethyl-4- [4- (4-fluorophenyl) -4-ethoxyimino-2-cyanobutylyl] -5-chloropyrazole (Compound No. 8-65) Manufacture of:

To 10 ml of a solution of 1.0 g of 1-methyl-3-trifluoromethyl-4-cyanoacetyl-5-chloropyrazole, 1.1 g of potassium carbonate and 0.6 g of sodium iodide in 10 ml of acetonitrile having a purity of 70% 1.5 g of 4- (1-ethoxyimino-2-bromoethyl) fluorobenzene was added at 0 ° C. The mixture was stirred at rt for 18 h. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The obtained residue was purified by chromatography on silica gel (eluent, n-hexane / ethyl acetate = 1/1) to give 1-methyl-3-trifluoromethyl-4- [4- (4-fluorophenyl 1.2 g of 4-ethoxyimino-2-cyanobutylyl] -5-chloropyrazole was obtained. Melting point: 73-75 degreeC.

Example 9:

1-methyl-3-trifluoromethyl-4- [4- (4-trifluorophenyl) -4-ethoxyimino-2-cyanobutylyl] -5-chloropyrazole (Compound No. 8-73 Manufacture of

In a solution of 7.5 g of 1-methyl-3-trifluoromethyl-4-cyanoacetyl-5-chloropyrazole, 8.2 g of potassium carbonate, and 5.4 g of sodium iodide in 225 ml of acetonitrile, 4-% having a purity of 86% 12.6 g of (1-ethoxyimino-2-bromoethyl) -α, α, α-trifluorotoluene were added at -5 ° C. The mixture was stirred at rt for 19 h. The reaction mixture was poured into iced water and washed with n-hexane. A concentrated sulfuric acid solution was added to the obtained aqueous layer to make the pH of the solution 1, which was extracted with ethyl acetate. The resulting extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give a residue. The residue is then washed with n-hexane to give 1-methyl-3-trifluoromethyl-4- [4- (4-trifluorophenyl) -4-ethoxyimino-2-cyanobutylyl ] 9.9 g of chloropyrazole was obtained. Melting point: 77-80 degreeC.

Example 10:

Preparation of 1-methyl-3-trifluoromethyl-4- [4- (4-trifluorophenyl) -4-oxo-2-cyanobutylyl] -5-chloropyrazole:

In a solution of 2 g of 1-methyl-3-trifluoromethyl-4-cyanoacetyl-5-chloropyrazole and 1.23 g of diisopropylethylamine in 40 ml of methylene chloride, 4- (1 having a purity of 91.6% 2.55 g of oxo-2-bromoethyl) -α, α, α-trifluorotoluene were added at 0 ° C. The mixture was stirred at rt for 18 h. The reaction mixture was then poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and the solvent was distilled off under reduced pressure to obtain a residue. The obtained residue was purified by chromatography on silica gel (eluent, n-hexane / ethyl acetate = 4/1) to give 1-methyl-3-trifluoromethyl-4- [4- (4-trifluoro Phenyl) -4-oxo-2-cyanobutylyl] -5-chloropyrazole was obtained.

Example 11:

Preparation of 1-methyl-3-trifluoromethyl-4- (2-bromo-2-cyanoacetyl) -5-chloropyrazole:

To a solution of 5.0 g of 1-methyl-3-trifluoromethyl-4-cyanoacetyl-5-chloropyrazole in 30 ml of chloroform, 7.0 g of bromine was added at room temperature. The mixture was stirred at room temperature for 3 hours, then washed with aqueous sodium hydrogen carbonate and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give a residue. The obtained residue was purified by chromatography on silica gel (eluent, n-hexane / ethyl acetate = 2/1) to give 1-methyl-3-trifluoromethyl-4- (2-bromo-2-cya 5.3 g of noacetyl) -5-chloropyrazole was obtained. Melting point: 76-77 degreeC.

Example 12:

Preparation of 1-methyl-3-trifluoromethyl-4- (2-chloro-2-cyanoacetyl) -5-chloropyrazole:

A mixture of 2.0 g of 1-methyl-3-trifluoromethyl-4-cyanoacetyl-5-chloropyrazole, 2.1 g of N-chlorosuccinic imide (abbreviated as NCS) and 20 ml of methylene chloride was added for 3 hours. Reflux for a while. After cooling, the reaction mixture was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give a residue. The obtained residue was purified by chromatography on silica gel (eluent, n-hexane / ethyl acetate = 2/1) to give 1-methyl-3-trifluoromethyl-4- (2-chloro-2-cyano 0.5 g of acetyl) -5-chloropyrazole was obtained.

Representative examples of the compound according to the present invention are shown in Tables 4 to 10. ¹ H-NMR data of the compound is shown in Table 11.

In the following, examples will be described for preparing formulations containing a compound of the invention. However, it should be noted that the type and incorporation rate of the additives are not limited to those described in the following examples, and may be changed over a wide range. Note that in the formulation examples described below the term "parts" refers to "parts by weight".

Example 13: Wettable Powder Formulations

40 parts of a compound of the present invention

Diatomite 53 parts

Higher Alcohol Sulfate Part 4

Alkyl naphthalenesulfonate 3 parts

By mixing the given ingredients and micronizing them into fine particles, we obtain a wettable powder formulation in which the compound of the present invention is 40% content based on the active ingredient.

Example 14: Emulsifiable Concentrate Formulations

30 parts of a compound of the present invention

Xylene Part 33

Dimethylformamide 30 parts

Polyoxyethylene alkyl allyl ether 7 part

By mixing the given ingredients and preparing them in solution, an emulsified concentrated formulation is obtained in which the compound of the present invention is 30% content based on the active ingredient.

Example 15 Powder Formulation

Compounds of the Invention 10 Part

Talc89

Polyoxyethylene alkyl allyl ether 1 part

By mixing the given ingredients and micronizing into fine particles, a powder formulation is obtained in which the compounds of the present invention are 10% content based on the active ingredient.

Example 16: Granule Formulation

5 parts of a compound of the present invention

73 parts of clay

Bentonite 20 Part

Dioctylsulfosuccinate sodium salt 1 part

Sodium phosphate 1 part

The above given ingredients are mixed, completely ground, water is added, then kneaded, granulated and further dried to obtain a granule formulation in which the compound of the invention is 5% content based on the active ingredient.

Example 17 Suspension Concentrate Formulations

Compounds of the Invention 10 Part

Sodium Ligninsulfonate Part 4

Sodium Dodecylbenzenesulfonate 1 part

Xanthan Rubber0.2

84.8 parts of water

By mixing the given ingredients and grinding by wet grinding to a particle size of less than 1 μm, a suspension concentrate is obtained in which the compounds of the present invention are in a 10% content based on the active ingredient.

Industrial use of the present invention

Now, how the compound according to the invention acts as a control agent for controlling harmful insects and mites will be described with reference to the test examples described below.

Test Example 1 Efficacy on Spotted Mites

Fifteen healthy adult female spotted mites that acquired resistance to organic phosphorus insecticides were planted in a jar about 10 cm deep and released on the first bony leaves of kidney beans 7-10 days after germination. The wettable powder formulations containing the compounds of the present invention prepared according to Example 13 were diluted with water to a concentration of 125 ppm based on the compounds of the present invention and the solution prepared was sprayed onto the mites. The mites on the plants were then placed in a room maintained at a temperature of 25 ° C. and a relative humidity of 65%. Three days later, the mortality rate of mites is examined. The test was performed repeatedly, and chlordimeform (conventional acaricide) was used as a reference standard. In this test, the mortality of mites with 125 ppm of standard acaricide was 13%.

As a result, the following compounds showed 100% mortality as efficacy after 3 days. Note that the following compound numbers correspond to those shown in Tables 4-9.

Compound number:

Test Example 2 Efficacy on Tangerine Mite:

Ten adult female tangerine mites were released on tangerine leaves placed in a Petri dish. The emulsifiable concentrate containing the compound of the present invention prepared according to Example 14 was diluted with water to a concentration of 125 ppm based on the compound of the present invention, and the solution was muffled on tangerine leaves using a rotary spraying mechanism. Sprayed on. The mites which received the spray were placed in a room maintained at a temperature of 25 ° C. and a relative humidity of 65%. Three days later, the mortality rate of mites is examined. The test was performed repeatedly and chlordimethform (conventional acaricide) was used as a reference standard. In this test, the mortality rate of the mites with 125 ppm of standard acaricide was 50%.

As a result, the following compounds showed 100% mortality as efficacy after 3 days. Note that the following compound numbers correspond to those shown in Tables 4 to 10.

Compound number:

Test Example 3 Efficacy on Cotton Aphid

Healthy adult cotton aphids were planted in a jar about 10 cm deep and released on cucumber leaves 10 days after germination. After one day, all of the released adult aphids were removed to obtain cucumber leaves with nymphs of aphids. An emulsifiable concentrated formulation containing a compound of the present invention prepared according to Example 14 was diluted with water to a 125 ppm concentration based on the compound of the present invention and the solution prepared was sprayed onto the aphid. The aphids on the plant were then placed in a room maintained at a temperature of 25 ° C. and a relative humidity of 65%. After 5 days, the mortality rate of aphids is examined. The test was performed repeatedly.

As a result, the following compounds showed 100% mortality as efficacy after 5 days. The following compound numbers correspond to those shown in Tables 5, 6 and 8, and note that PIRIMICARB (traditional pesticide) was used as a reference standard.

Compound number:

Claims (4)

Compound represented by the following formula (1): [Formula 1] [Wherein A represents selected from the group consisting of the following groups A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11 and A12: Wherein X ₁ , X ₂ , X ₃ and X ₄ each independently represent hydrogen, halogen, C _1-6 alkyl or C _1-6 haloalkyl; X ₅ represents hydrogen, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 haloalkenyl or optionally substituted phenyl C _1-6 alkyl; X ₆ and X ₇ each independently represent C _1-6 alkyl, or X ₆ and X ₇ together may form a 5-8 membered ring; Y is cyano, C _1-6 alkyl, C _3-6 cycloalkyl, phenyl which benzene ring may be substituted with C _1-6 alkyl, G _1, G ₁ as optionally substituted optionally substituted with phenyl phenoxy, G ₁ when, as a phenylthio C _1-6 alkyl, G ₁ a benzene ring which may be optionally substituted phenylthio, phenoxy benzene ring by C _1-6 alkyl, G _1, which may be substituted by G ₁ substituted with G ₁ a phenyl optionally substituted sulfinyl, the benzene ring is phenyl, which is optionally substituted phenylsulfonyl, benzene ring, phenyl- sulfinyl C _1-6 alkyl, G _1, which may be substituted by G ₁ may be substituted with G _1-sulfonyl C _1-6 alkyl, G ₁ as an optionally substituted anilino, a benzene ring is Reno C _1-6 alkyl, optionally substituted thienyl, thiophene ring with G ₁ is not optionally substituted with G ₁ is optionally substituted by G ₁ a thienyl C _1-6 alkyl, optionally substituted pyridyl, and a pyridine ring in G ₁ can be made to the pyridyl C _1-6 alkyl which may be substituted by G ₁ It represents a group selected from the group true; Z represents oxygen, sulfur, or nitrogen substituted with hydrogen or C _1-6 alkyl; G ₁ is nitro, cyano, halogen, C _1-6 alkyl, C _2-6 alkenyl, C _2-6 alkynyl, C _3-8 cycloalkyl, C _1-6 haloalkyl, C _2-6 haloal Kenyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _2-6 alkenyloxy, C _2-6 haloalkenyloxy, C _2-6 alkynyloxy, C _1-6 alkylthio, C _{1- 6} alkylsulfinyl, C _1-6 alkylsulfonyl, C _1-6 alkylamino, di - (C _1-6 alkyl) amino, tri - (C _1-6 alkyl) silyl, C _1-6 alkoxy C _{1- 6} alkyl, C _1-6 alkylthio C _1-6 alkyl, C _1-6 alkylsulfinyl C _1-6 alkyl, C _1-6 alkylsulfonyl C _1-6 alkyl, C _1-6 alkylcarbonyl, C _1-6 alkoxycarbonyl, the benzene ring is optionally substituted by phenyl C _1-6 alkoxy, G ₃ with a phenyl C _1-6 alkyl, a benzene ring which may be substituted with G ₂ may be substituted with G _2-thienyl, a G ₂ is optionally substituted pyridyl, optionally substituted pyridyloxy, optionally substituted phenyl, or G ₄ represents an optionally substituted phenoxy with a G ₄ to G _2; G ₂ represents C _1-6 alkyl, halogen, C _1-6 haloalkyl or C _1-6 haloalkoxy; G ₃ represents C _1-6 alkyl or halogen; G ₄ is nitro, cyano, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _1-6 alkylthio, C _1-6 alkylsulfinyl , C _1-6 alkylsulfonyl, C _1-6 alkylamino, di- (C _1-6 alkyl) amino, C _1-6 alkylcarbonyl or C _1-6 alkoxycarbonyl); B represents phenyl substituted with W or heterocyclic group substituted with W Wherein W is nitro, cyano, halogen, C _1-6 alkyl, C _3-8 cycloalkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _1-6 alkylthio , C _1-6 alkylsulfinyl, C _1-6 alkylsulfonyl, C _1-6 alkylamino, di - (C _1-6 alkyl) amino, C _1-6 alkylcarbonyl, C _1-6 alkoxycarbonyl , any denotes an optionally substituted phenoxy or a phenyl substituted by G ₅ G _5, Wherein G ₅ is nitro, cyano, halogen, C _1-6 alkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 haloalkoxy, C _1-6 alkylthio, C _1-6 alkyl Sulfinyl, C _1-6 alkylsulfonyl, C _1-6 alkylamino, di- (C _1-6 alkyl) amino, C _1-6 alkylcarbonyl or C _1-6 alkoxycarbonyl; Heterocyclic groups substituted with W are triazolyl, thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, pyrazolyl, imidazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, thienyl, furyl, pyrrolyl , Pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl are any one group selected from the group consisting of; R is hydrogen, C _1-6 alkyl, a group represented by formula COR ₁ , a group represented by formula CSR ₁ , a group represented by formula SO ₂ R ₂ , C _1-6 alkylcarbonyloxy C _1-6 alkyl, C _3-6 cycloalkylcarbonyloxy C _1-6 alkyl or optionally substituted phenylcarbonyloxy C _1-6 alkyl Wherein R ₁ is C _1-12 alkyl, C _3-6 cycloalkyl, C _1-6 haloalkyl, C _1-6 alkoxy, C _1-6 alkylthio, C _1-6 alkylamino, di- (C _1-6 alkyl) amino, optionally substituted phenyl C _1-6 alkyl, optionally substituted phenyl C _1-6 alkoxy or optionally substituted phenyl, R ₂ represents C _1-12 alkyl or optionally substituted phenyl) ; However, B is either phenyl substituted with W or pyridyl substituted with W, R is hydrogen, C _1-6 alkyl, a group represented by formula COR ₁ , a group represented by formula CSR ₁ or a formula SO ₂ R _When any of the groups represented by ₂ , A is not benzyl substituted with G ₁ ]. A method for preparing a compound represented by the following Chemical Formula 2, wherein the compound is prepared by reacting a compound represented by the following Chemical Formula 3 with a compound represented by the following Chemical Formula 4 in the presence of a base: [Formula 2] (Wherein A and B are as defined in claim 1), [Formula 3] (Wherein A is as defined above), [Formula 4] (Wherein B is as defined above and L is a leaving group). A method for preparing a compound represented by the following Chemical Formula 2, wherein the compound is prepared by reacting the compound represented by the following Chemical Formula 5 with the compound represented by the following Chemical Formula 6. [Formula 2] (Wherein A and B are as defined in claim 1), [Formula 5] (Wherein B is as defined above), [Formula 6] A-L (Wherein A and L are as defined in claim 2). Insecticides and acaricides containing a compound represented by the following formula (1) or a salt thereof as an active ingredient: [Formula 1] (Wherein A, B and R are as defined in claim 1).