WO1998042683A1 - Triazole compounds, process for the preparation thereof, and insecticides and miticides - Google Patents

Abstract

Compounds of general formula (I); a process for the preparation thereof; and insecticides and miticides: wherein A is C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C8 cycloalkyl, optionally substituted phenyl or the like; B is optionally substituted phenyl or an optionally substituted heterocyclic group; R1 is C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl or the like; and R2 is hydrogen, C¿1?-C6 alkyl, COR?6¿ or the like.

Description

 Meitriazole compounds, their production methods and insecticides and acaricides Technical fields:

 The present invention relates to a triazole compound, a method for producing the same, and an insecticide and acaricide. Background art:

 Conventionally, many insecticides and acaricides have been used, but their efficacy is inadequate and their use is limited due to drug resistance problems. There is a need for drug development.

 Compounds having a structure similar to the compound of the present invention are disclosed in JP-A-53-92769, JP-A-5151493, and EP189690. The following thiazole compounds are described in gazettes, WO96 / 33995, and the like.

(In the formula, r, and r ₂ each represent a hydrogen atom, a halogen atom, C,- _(; represents an alkyl group or the like, and r ₃ represents an aromatic hydrocarbon group, a pyrazolyl group, or the like.)

In addition, WO97 / 4099 published after the earliest priority filing date of the present invention describes a compound represented by the following formula.

(In the formula, Q and A represent various heterocycles, etc., E represents CN etc., B represents H and others.) However, a compound which is 1,2,4-triazole having a strong Q is 1,2,4-Triazole-3-3-yl compound is unsubstituted at the 1-position, only 2,4 triazole-1yl compound is synthesized (Table 19, V31) Compounds are listed in Table 10 It is only shown. Disclosure of the invention:

 The present invention provides a compound represented by the general formula (I):

[In the formula, A, C _i-6 alkyl groups, C _{2 6} alkenyl groups, C _{2 6} alkynyl groups, C ₃ - ₈ cycloalkyl group, (halogen atom, a nitro group, Shiano group, alkyl Le groups, C ! — ₆ haloalkyl group, ₆ alkoxy group, (; optionally substituted with haloalkoxy group) phenyl group, formula

(Wherein, the R ^3, R ^'1 represents a hydrogen atom or an alkyl group, R ⁵ is identical or different halogen atoms, two collected by filtration group, Shiano group, C, - ₆ alkyl group, C, - ₆ Nono b benzyl group, or, (halogen atom, _alkyl group, C ₆ haloalkyl group, ₆ alkoxy group, C, represented by the a alkyl group, n represents an integer of 0 or from 1 to 5)!. - _(It may be substituted by ₆ alkylthio groups.) Represents a heterocyclic group, and the heterocyclic group represents a pyridyl group, a pyrazolyl group, a furyl group, a phenyl group, a benzoyl group, a benzofuranyl group or a benzochenyl group.

B is (a halogen atom, a nitro group, Shiano group, an alkyl group, Ji, - ₆ /, lower alkyl group, ₆ alkoxy group, C i alkylthio group, may be substituted by flicking ₆ haloalkoxy group) Fuweniru group , (Halogen atom, nitro group, cyano group

, C, alkyl group, — (; haloalkyl group, C i — alkoxy group, C i — (i al Represents a heterocyclic group, which may be substituted with a quinthio group. The heterocyclic group is a pyridyl group, a pyrazolyl group, a furyl group, a phenyl group, a thienyl group, a thiazolyl group, or a 1,2,3-thiadiazolyl group. Represent.

R ¹ is C, - ₆ alkyl group, a haloalkyl group, C ₆ alkoxy ₆ 7 alkyl group, Hue sulfonyl Ji s alkyl group, C ₃ - ₈ cycloalkyl group, C ₃ - ₈ cycloalkyl ₆ alkyl group, C ₂ - alkenyl groups, C ₂ - ₆ alkynyl groups, C ₂ - _beta haloalkenyl groups, C ₂ - ₆ haloalkynyl groups, C, - (; alkylcarbonyl groups, C alkoxycarbonyl C _fi alkyl group, Application Benefits Arukirushi Li C _(alkyl Represents a group.

R ² represents a hydrogen atom, _G an alkyl group, COR ⁶ C Arukirusurufu Oniru group or Fuwenirusurufo two group, the R ^e (: _beta alkyl group, Fuweniru group, Hue alkenyl, - ₆ alkyl group, Fuwenokishi C _i-6 An alkyl group, a C _{3 -B} cycloalkyl group, an alkoxy group, a pyridyl group, a furyl group or a phenyl group which may be substituted with a halogen atom.] An insecticide and acaricide containing a compound.

 In the triazole compound represented by the above formula (I) of the present invention,

Examples of the C n alkyl group in the definition of A include straight-chain and branched alkyl such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isoptyl, t-butyl, neopentyl, and hexyl. And the C ₂ -e alkenyl group includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl and the like, and as the C _{2 -r>} alkynyl group, is Echiniru, propargyl, and the like, C ₃ - is the ₈ cycloalkyl group, Shikuropuro pills, sik Robuchiru, cyclopentyl, cyclohexyl and the like cyclohexane, and substituent of Fuweniru group which may be substituted Halogen atoms such as fluorine, chlorine and bromine, nitro group, cyano group, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, C <alkyl groups having straight-chain and branched chains such as isopropyl, t-butyl, neopentyl, hexyl, etc., chloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, 22, 2 — trifluoroethyl, fluorochloromethyl, C, ₁₆ haloalkyl groups such as difluoromethylchloromethyl, penfluorofluorethyl, etc., methoxy, Ci-s alkoxy group such as ethoxy, propoxy, isopropoxy, butoxy, t-butoxy, trifluoromethoxy, 1,1,2,2—tetrafluoroethoxy, trichloromethoxy, difluorome C, such as butoxy, include over ₆ haloalkoxy group and a phenylpropyl group. Examples of the _6- alkyl group of R ³ and R "of the benzyl group include methyl, ethyl, propyl, isopropyl, butyl, isoptyl, t-butyl and the like, and the substituent R ⁵ , Fluorine, chlorine, bromine and other halogen atoms, nitro, cyano, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isopropyl, t-butyl, neopentyl, hexyl equal linear and 〇 having a branched, _-6 alkyl group, click Rorome chill, Jifuruorome chill, Application Benefits click Rorome Chi le, Bok Li Funoreorome chill, 2, 2, 2 - Application Benefits Funoreoroechiru, Furuoro click Rollo methylation, Jifuruoroku C-haloalkyl groups such as lorometyl and pennofluorethyl, etc. Examples of the heterocyclic substituent include halogen atoms such as fluorine, chlorine, and bromine. , Methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isoptyl, t-butyl, neopentyl, hexyl, etc.C! -6 alkyl groups having a straight or branched chain, chloromethyl, difluoromethyl, etc. , Trichlorometyl, trifluorometyl, 2,2,2 — C, ₁ such as trifluorometyl, fluorochlorometyl, difluorochlorometyl, pennofluoremetyl _; haloalkyl group, methoxy, ethoxyquin , Propoxy, isopropoxy, butoxy, t-butoxy, etc., C 1-0 alkoxy groups, methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, isobutylthio, t-butylthio, etc. include C _i-6 alkylthio group having a branched. as a heterocyclic ring , 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 3-virazolyl group, 4-virazolyl group, 2-furyl group, 3-furyl group, 2- Chenyl group, 3 —Chenyl group, 2 —Thiazolyl group, 4 —Thiazolyl group, 5 —Thiazolyl group, 2 —Benzofuryl group, 3 —Benzofuryl group, 2 —Benzochenyl group, 3 — Benzothenyl groups are mentioned.

Examples of the substituent of the phenyl group and the heterocyclic group in the definition of B include a halogen atom such as fluorine, chlorine, and bromine, nitro, cyano, methyl, ethyl, propyl, and isopropyl. Pill, butyl, sec —butyl, isoptyl, t —butyl, neopentyl, hexyl, etc., straight-chain and branched C,-6 alkyl groups, chloromethyl, difluoro Haloalkyl groups such as rometyl, trichloromethyl, triphenylenomethyl, 2,2,2—trifluoroethyl, fluorochloromethyl, difluorochloromethyl, pennofluorethyl, methoxy, ethoxy, Purobokishi, Lee Sopuropoki shea, butoxy, t - butoxy, etc. C, - ₆ alkoxy groups, main Chiruchio, Echiruchio, pro Piruchio, Lee Sopuro Piruchio, Puchiruchio, sec - Puchiruchio, Lee Su Wu Chiruchio, t one Puchiruchio like linear And haloalkoxy groups such as branched C alkylthio groups, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, trichloromethoxy, difluoromethoxy and the like. Heterocycles include 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-virazolyl, 4-pyrazolyl, 2-furyl, and 3-furyl Group, 2—Chenyl group, 3-Cthenyl group, 2—Thiazolyl group, 4-Thiazolyl group, 5—Thiazolyl group, 1,2,3—Thiadiazolyl4_yl, 1,2,3 —Thiadiazole— 5 —yl.

 The phenyl group, benzyl group and heterocyclic group in A and B may have a plurality of substituents, and those substituents may be the same or different.

Examples of the C alkyl group in the definition of R ¹ include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, pentyl, neopentyl, hexyl, and the like, and a haloalkyl group. Chloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, etc., and the alkoxy Ci alkyl group is methoxymethyl. Phenyl, methoxyethyl, ethoxymethyl, ethoxyethyl, methoxypropyl, ethoxypropyl, etc., and the phenyl-alkyl group is benzyl, phenyl, phenylpropyl, α-methylbenzyl. etc. can be mentioned, C ₃ - is the a cycloalkyl group, sik Ropuro pills, sik Ropenchiru, consequent Roeki Le, and the like, c ₃ - is a ₈ a cycloalkyl C alkyl group, consequent Ropuro Pirume chill, sik Ropuro Piruechiru, sik Ropenchirume chill, Kishirue chill and the like to the consequent B, C ₂ - and ₆ alkenyl group and is, Bulle, 1 - propenyl, 2 - propenyl, 1 - butenyl, 2 - butenyl, 3 - butenyl, blanking evening Jeniru and the like, C ₂ - is a ₆ alkynyl group, Echiniru , Propargyl, etc. And C 2-6 haloalkenyl groups include 3—chloro-one 1-propenyl, 2—chloro-one—1-propyl, 3—chloro-2—propenyl, and 2— Loro 2-propenyl, 1-chloro 2-propidyl and the like. Examples of the C _{2 -G} haloalkynyl group include

, Chloroethynyl, 11-chloropropargyl, etc., and the 6-alkylcarbonyl group includes acetyl, ethylcarbonyl, propylcarbonyl, isopropyl propylcarbonyl, butylcarbonyl, sec-butyl Carbonyl, t-butylcarbonyl, neopentylcarbonyl, hexylcarbonyl and the like. Examples of the _16- alkoxycarbonyl C n alkyl group include methoxycarbonylmethyl, methoxycarbonylethyl, and ethoxycarbonylmethyl. , et DOO Kin carbonyl Echiru, main butoxycarbonyl propyl, et butoxycarbonyl propyl, etc. can be mentioned, et al is, in the Application Benefits ₆ Arukirushi Li Le alkyl group, Bok Li main Chirushi Li Rume chill, Application Benefits Echirushi Li Rume chill , Trimethylsilyl retyl, triethylsilyl Rutile and the like.

Examples of the alkyl group in the definition of R ² include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, neopentyl, and hexyl, and a C i -e alkylsulfonyl group. the was, main Chirusuruhoniru, E Ji Rusuruhoniru, pro Pirusuruhoniru, Lee Sopuro Pirusuruhoniru, Buchirusuruhoni Le and the like, C in R ^B of Ashiru group, - is a 6 alkyl group, methylation, Ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, neopentyl, hexyl, etc., and the phenyl, ^ alkyl groups include benzyl, phenyl, etc. is a full We Bruno carboxymethyl d group, off We Roh Kishime chill, full et Bruno Kishechiru, full et Nokishipuro pills and the like, C ₃ - ₈ Examples of the cycloalkyl group include cyclopropyl, cyclopentyl, and cyclohexyl, and examples of the alkoxy group include methoxy, ethoxy, propoxy, isopropoxy, butoxy, and t-butoxy. Examples of the phenylalkyl group include benzyl, phenethyl, phenylpropyl, α-methylbenzyl and the like, and examples of the pyridyl group include chlorine, bromine, fluorine and the like. Examples include 2-pyridyl, 3-pyridyl or 4-pyridyl which may be mono-, di- or tri-substituted by a halogen atom. The compound of the present invention has two kinds of isomers, E-form and Z-form, both of which are included in the present invention. Further, in the compound of the present invention, when R ² is a hydrogen atom, the following tautomers may exist. Although it is thought that it mainly exists in the enol form (I), the present invention includes all of these tautomers and mixtures thereof.

 (I) Representative examples of the compound of the present invention are shown in Table 1.

The abbreviations in the table have the following meanings. (The same applies to Table 2 and below)

: οε6: 626

 : SS6

: SS6:

 : 61.6: 81-6: 6 ngu, Jd! Jdu 13

0 O O 0OH

: 9L6: 6

 : 0Ι6: 66

 6: εβ: S6:

S0n0 / 86df / XDd £ 89h / 86 O / W

: Re

: 9m: em

S0 i0 / 86df / X3d £ 89h / 86 O

* When R., is hydrogen, a tautomer exists, and in other cases, there exists an E-form and a Z-form. For convenience, the eno-form Z-form is shown. Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

W

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

A B R, R.,

P h 2.6-F.,-Ph n H e x H

2— F-P h 2, 6-F-P h n H e x H

3— F— P h 2, 6— F-P h n H e x H

 2, 6-F.,-P h n H e x H

2— c 1— p h 2. 6— F., — P h n H e x H

3— C 1— P h 2, 6— F.,-P h n H x H

A — C 1 one P h 2, 6— F.,-P hn H ex H _ or _r _ pu 2, 6-F,-P hn H ex H

3— β _r — ph 2, 6— F., — P hn H ex H

 2. 6-F,-P hn He x H — I— ph 2, 6— F., — P hn H e x H

3— I— p h 2, 6— F, — P h n H e x H

4— I— p h 2, 6-F,-P h n H e x H

2, 3— F, — p h 2.6-F-P h n H x H

2, 4-F.,-Ph 2, 6-F,-P h n H ex H

2, 5-F,-P h 2, 6— F., — Ph n H ex H

2, 6-F,-P h 2. 6-F.,-P h n H ex H

3, 4-1 F-1 P h 2, 6-F,-P h n H ex H

3, 5— F., — P h 2, 6— F., — P h n H ex H

2. 3-C 1,-P h 2, 6— F ·, — P h n H ex H

2,4-C1, 1, Ph2, 6-F. One Ph n H e x H

2, 5-C 1 one P h 2, 6— F .'— P h n H x H

2, 6-C 1 „-P h 2, 6-F,-P h n H e x H

3, 4-C 1,-P h 2, 6— F., — P h n H ex H

3, 5-C and one P h 2, 6— F .'— P h n H x H

2-C 1 -3-F-Ph 2, 6-F.,-P h n H ex H

2 -C 1 -4-F-Ph 2, 6-F.,-P h n H ex H

2— C 1-δ-F-Ph 2, 6-F,-P h n H ex H

3— C I 1 2— F— Ph 2, 6-F P h n H ex H

4−1 C I−1 2— F— Ph 2, 6-F „-P h n H ex H

5— C 1 -2-F-Ph 2. 6-F,-P hn H ex H Table 1 (continued) Dimensions

 A B R,

 2 -C 1 -6-F-Ph 2 6— F — P h n H e x H

 2, 6— F — P h n H e x H

2, 6— F — P h n H x H d — then 1 o r ~ r n 2, 6-F-P H n H e x H

2, 6— F ~ P hn H 6 x H _,, 4— r _{: ί} — rn 2, 6— p — phn H x H, 6, ο— r _{; i} — r η 2, 6— F — P h H 6 X

2 o, b— r _{: i} — rn 2, — _f) — phn H ex

Z, 4 o— r _{; i} — rn 2, 6— F — P h Π H Θ X

, 4, b — h _{; i} — rn 2 β — p — ph Π H 6 X, 4 b— r _{: i} — rn 2 6— F., — P hn H ex PI — C 1 — Δ, o — r — Rn 2 6— F ".> — P h Π HGXH

4— then 1— b— to., 1 de l n H e x

S 1 — i 4— r ~ r Π 2 — p, _} — phn H β x s tdo — rr Π 2 _t 6— F — Ph Π H 6 XH — s 1 — 0 b— r ^ ^— rn 9 6— F.> — P hn H β x H 1 ° t, ― Γ ― Π 2, G— F "— P h Π HGXH — C \ — A — P — p H 2 ₍ 6— F — P hn H β x H

 2, 6-F ~ P h n H e x H ·, 6— F — P h n H 6 x H

2, 3, 6-C 1 _{; 1} -P h 2, 6-F,-P hn H ex H

2, 4, 5—Cl: Ph 2, 6—F. One P h n H e x H

2, 4, 6-C 1 _{: i} -P h 2, 6-F ■> ~ P hn M ex H

3, 4, 5— C i Ph 2, 6-F,-P h n H e x H

2, 3, 4, 5— F ₄ -Ph 2, 6— F., — P hn H ex H

2 3, 4, 6— F- “Ph 26-F, -Ph n H x H

2, 3, 5, 6 ~ F ₄ -P h 2, 6-F,-P hn H ex H

2, 3, 4, 5 6-F-P h 2, 6— F — P h n H e x H

2. 3, 4, 5, 6— C ₁₅ — Ph 2, 6-F,-P hn H ex H

2— F— P h 2— C F: “P h n H e K H

3-F-Ph 2— CF: “P hn H ex H Table 1 (continued)

A B R R.,

4-F-P h 2-CF _{; f} -P hn H ex H

2 -C 1-P h 2-C F (-P h n H x H

3-C 1Ph 2-CF _;! -P hn H ex H

4 1 C 1 1 P h 2-CF _{: i} -P hn H ex H

2.3-F,-P h 2-CF _{; (} -P hn H ex H

2, 4-FP h 2-CF _{: i} -P hn H ex H

2, 5 - F, - P h 2- CF: -! P hn H ex H

2. 6-F,-P h 2-CF _{: i} -P hn H ex H

3, 4 一 F „— Ph 2-C F-P h n H e x H

3, 5-F,-P h 2-C F,-P h n H e x H

2-C 1 -6-F-Ph 2-CF _{: f} -P hn H ex H

P h h 1 n H e x H

2 -F-Ph h 1 n H e x H

3-F-Ph h 1 n H e x H

4-F-Ph h 1 n H e x H

2— C 1 Ph h 1 n H ex H

3-C 1 Ph h 1 n H e x H

4 1 C 1 1 Ph h 1 n H e x H

2— B r— P h h 1 n H ex H

3— B r— P h h 1 n H ex H

4-B r-P h h 1 n H e x H

2-I-P h h 1 n H e x H

3—I-Phh1nHexH

4 1 I 1 P h h 1 n H e x H

2, 3-F., — P h h 1 n H ex H

2, 4-1 F.,-P h h 1 n H e x H

2, 5-F ·,-P h h 1 n H e x H

2. 6-F ·, — P h h 1 n H ex H

3.4-1 F., — P h h 1 n H ex H

3.5-F ,,-P h h 1 n H e x H

2. 3—C 1., one P hh 1 1 n H ex H Table 1 (continued)

讓 s 讓 讓 s es ΐ ΐ

 X X X X X X X X X X X X X X X X X X X X X X X X X X X X

X X X X X X X X X X X X X X X X X

a.

 a-

IX u

<

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

BR, R ,, 6-F,-P h 2, 4, 6— F _{: i} — Ph M e H — CI-1 6— F— Ph 2.4, 6— F _{: i} — Ph M e H — F — P h 2, 3-F, -6-CF _{: i} -Ph Me HF-Ph 2, 3-F, -6-CF _{: 1} -Ph Me HF-Ph 2, 3— F ₂ — 6— CF _: ,-Ph Me H, 6-F.,-P h 2.3-F ₂ — 6— CF _{: i} -Ph e H -C 1 6-F— Ph 2, 3-F, -6 _{-CF:! -Ph Me H - F-} P hh 2 Me HF-Ph h 2 M e HF-Ph h 2 Me H, 6 - F, - P hh 2 e HC 1 -6-F-Ph h 2 M e H-F-P hh 3 M e HF-Ph h 3 Me HF-Ph h 3 Me H, 6-F.,-P hh 3 Me H — CI-6-F-Ph h 3 M e H -F -Ph h 4 Me H -F-Ph h4 Me H -F-Ph h 4 Me H, 6— F.,-P hh 4 Me H — CI-6-F— Ph h 4 Me H -F- Ph h 5 M e H -F-Ph 5 Me H -F-Ph h 5 Me H, 6-F.,-P hh 5 M e H -C 1 -6-F-Ph h 5 M e H -F -Ph h 6 M e H -F-Ph h 6 M e H -F-Ph h 6 M e H. 6-F.,-P hh 6 M e H — CI-6 — F— Ph h 6 Me H Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

B

 -R, R., — CI 1 6-F— P hh 19 Me HFP hh 20 Me HF-Ph h 20 Me e HF-Ph h 20 Me H. 6-F-P hh 20 Me HC 1- 6 -F- P hh 20 Me HF-Ph h 2 1 Me HF-Ph h 2 1 Me HF-Ph h 2 1 Me H. 6— F., — P hh 2 1 Me H-CI 1 6-F — P hh 21 Me HFP hh 22 Me HF-Ph h 22 Me HF-Ph h 22 Me H, 6— F.,-P hh 22 Me H — CI one 6— F— Ph h 22 M e HF-Ph h 23 Me HFP hh 23 Me HF-Ph h 23 Me H. 6-F ,,-P hh 23 Me H — CI 1 6 — F— P hh 23 Me HF-Ph h 24 Me HF-Ph h 24 Me HFP hh 24 Me H, 6-F ·, — P hh 24 Me H — C 1 6—F— P hh 24 Me H -FP hh 25 Me H -FP hh 25 Me H -FP hh 25 Me H. 6-F.,-P hh 25 M e H -C 1 -6 -FP hh 25 M e H

2, 6-F.,-P hi P r H ΐ 赃

X X X X X X X X X x a: X X X X

a-. Q CQ CQ CQ CQ CQ CQ CQ CQ

., a. a. a.

a. CL a. a. a.

 a

<

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

A B R, R.,

4-F- P h h 1 g 5 H

2, 6-F,-Ρ h h 1 g 5 H

2— C I 1 6— F— P h h 1 g 5 H

 2, 6-F P h g 6 H

3 _ p _ p ^ 2, 6-F-P h g 6 H

4 p _ p ^ 2, 6—F. One P h g 6 H

2, 6— F — P h 2. 6-F,-P h g 6 H

 2, 6— F., — Ph g 6 H

2— F— P h h 1 g 6 H

3— p— p h h 1 g 6 H

4— p— p h h 1 g 6 H

2, 6— F., — P h h 1 g 6 H

2— C 1 1 6— F-P h h 1 g 6 H

2 -F-P h 2.6-F-P h g 7 H

3 -F-P h 2, 6-F P h g 7 H

4-F-Ph 2, 6-F,-P h B 7 H

2.6-F.,-P h g 7 H

2— C 1 1 6— F— P h 2, 6-F,-P h g 7 H

2 -F-P h h 1 g 7 H

3— F— P h h 1 g 7 H

4-F- P h h 1 g 7 H

2, 6-F,-P h h 1 g 7 H

2 -C 1 1 6— F— Ph h 1 g 7 H

 2, 6-F,-P h g 8 H

3— F— P h 2, 6— F ·, — P h g 8 H

 2. 6— F., — P h g 8 H

2, 6-F,-P h 2. 6 _ F.,-P h g 8 H

2— C 1 1 6— F— P h 2, 6-F,-P h g 8 H

2- F- P h h 1 g 8 H

3-F-Ph h 1 g 8 H

4- F-P h h 1 g 8 H

2, 6— F., — P hh 1 g 8 H Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

BR, R, I F— P hh 1 Me g 18, 6-F,-Ρ hh 1 Me g 18 — C 1 6— F-Ph h 1 Me g 18-F-Ph 2. 6— F, — PhMeg19-F-Ph2.6-F.,-PhMeg19-F-Ph2.6-F.,-PhMeg19, 6-F.,-Ph2 , 6— F., — P h Me g 19 — C 1-6-F-P h 2.6-F,-P heg 19-F-Ph h 1 Me g 19-F-Ph h 1 Me g 19 -F-Ph h 1 Me 19.6-F.,-P hh 1 Me g 19-C 1 -6-F-Ph h 1 Me g 19-F-Ph 2, 6— F, — P h Me g 20-F-Ph 2, 6-FP h Me g 20-F-P h 2, 6-F,-P h Me g 20.6-FP h 2, 6-F,-P heg 20-C l- 6-F-Ph 2, 6-F.,-P h M eg 20-F-Ph h 1 Me g 20 h 1 Me g 20-F- P hh 1 Me g 20. 6— F., — P hh 1 M eg 20 -C 1 -6-F-Ph h 1 M eg 20

2. 6-F,-P h Me g 21 -F-Ph 2. 6-F,-P h Me g 1 — F— P h 2, 6— F., — Ph Me g21, 6-F., Ph 2.6-F ·,-P h M e g21 -C 1 1-6-F-Ph 2.6-F,-P h M e g21 -F-Ph h 1 Me g 21 -F-Ph h 1 Me g21-F-P hh 1 M e g21, 6— F — P hh 1 M eg 21 Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

0 / ma ar

 CiD bo bo bo D bo bO t30 bo bO bD bO a.a., a.a, a..a.a.a.a.0-, 0-, a, a, a.a.a.a.Cu a,

 a

<

Table 1 (continued)

Table 1 (continued)

C 9

 () Halla 1¾

S0Zl0 / 86 <If / X3 <I € 89h / 86 ΟΑ \ 9

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

to Table 1 (continued)

A B R, R en

h 7 h 1 Me H

 〇

h 13 h 1 M e H h 14 h 1 M e H h 15 h 1 e H h 16 h 1 M e H h 17 h 1 M e H h 19 h 1 M e H h 20 h 1 M e H h 23 h 1 e H h 24 h 1 M e H h 26 h 1 M e H h 27 h 1 M e H

2-e-P h 2-C 1-P h e H

4 tBu—Ph2 -C1 -PhMe H

2-CF _;! -P h 2 -C 1-P h Me H

4-CF _{: i} -P h 2-C 1— Ph Me H

2 -OM e-P h 2 -C 1-P h M e H

4-O t Bu-Ph 2— C 1Ph M e H

4 One OCF _{: i} — Ph 2— C 1 One P h M e H

4— F— 2— OMe— Ph 2-C 1 Ph M e H

2 -C 1 -P h Me H h 12 -C 1 Ph M e H h 7 2-C 1 P H Me e H h 13 2-C 1 P H H 152 C 1 P h M e H h 16 2-C 1 one P h Me H h 17 2-C 1 one P h M e H h 19 2-C 1 one P h Me H h 202-C 1 one P h Me H h 23 2-C 1-P h Me H h 24 2-C 1 one P h M e H Table 1 (continued)

The compounds of the present invention shown in Table 1 can be produced as follows. Manufacturing method (i)

(I I) (I I I) (I-1)

(In the formula, A, B, and R ¹ have the same meanings as described above, and R represents a phenylsulfonyl group, a phenylsulfonyl group which may have a substituent such as a tosyl group, or a methylsulfonyl group. Represents a C! -S alkylsulfonyl group.)

 In the reaction, 1 mol of the compound represented by the formula (II) and 0.5 to 2 mol of the compound represented by the formula (III) are mixed with 0.5 to 2 mol of aluminum chloride in an inert solvent. The reaction is carried out in the presence of a Lewis acid such as chromium, stannic chloride or zinc chloride. Examples of the solvent used for the reaction include chlorobenzene, o-dichlorobenzene, and the like. The reaction temperature is preferably from 100 ° C. to the boiling point of the solvent used. The compound represented by the formula (II) as a starting material can be obtained as follows.

Base

RNH title ₂ + AC0C1 AC0NHNHR

 (VII) (VIII) (IX)

R ¹ X

 AC0NHN (R ') R AC (C1) = NN (R') R

 Base

 (X) (II)

(In the formula, A, R ¹ and R represent the same meaning as described above.)

That is, 1 mol of hydrazine (VII) protected with a tosyl group and 0.5 to 2 mol of acid chloride (VIII) represented by ACOC1 are combined with 0.5 to 2 mol of acid chloride (VIII). The compound represented by the formula (IX) is obtained by reacting in an inert solvent in the presence of a base to obtain a compound represented by the formula (IX), and alkylating the compound with an alkyl halide represented by R ¹ X. After obtaining the compound, the compound represented by the formula (II) can be obtained by further reacting with a chlorinating agent.

 Examples of the base that can be used in this reaction include alkali metal hydroxides such as sodium hydroxide and hydroxylating water, and carbonates such as sodium carbonate and potassium carbonate. Metal alkoxides such as sodium methoxide, sodium methoxide, sodium ethoxide, and potassium t-butoxide; and organic bases such as triethylamine, diisopropylethylamine, and pyridine. Can be exemplified.

 Examples of the solvent include halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride, aromatic hydrocarbons such as benzene and toluene, getyl ether, tetrahydrofuran (THF), and the like. Ethers, acetonitril and the like can be mentioned. In addition, the reaction can be carried out in a two-layer system such as water and toluene or black-mouthed form. The reaction temperature is preferably from 0 ° C to room temperature.

The reaction with the alkyl halide represented by R ¹ X is carried out by the reaction of alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate and carbonated lithium. N, N-dimethylformamide (DMF), dimethylsulfoxide (DMS0) in the presence of a base such as an organic base such as carbonate, triethylamine, diisopropylethylamine, and pyridine. The reaction is carried out in a solvent such as THF, acetonitril, hexamethylphosphoric acid triamide (HMPA), benzene or toluene. The reaction is preferably carried out uniformly, and proceeds smoothly from 0 to 100 ° C.

Examples of the alkyl halide represented by R ¹ X include methyl iodide, butyl iodide, propyl iodide, isopropyl iodide, butyl bromide, benzyl bumid, 2,2,2-tritrifluoroethyl — P — Toluenesulfonate and the like can be exemplified.

The imidoyl chloride represented by the following formula (II) is obtained by adding 0.5 to 10 mol of thionyl chloride, oxychlorine, phosphorus trichloride, etc. to 1 mol of the compound represented by the formula (X). Can be obtained by reacting with a chlorinating agent. The reaction is carried out without solvent or in a solvent such as benzene, toluene, chloroform, carbon tetrachloride, etc., from room temperature. It is carried out in the temperature range up to the boiling point of the medium (the boiling point of the chlorinating agent).

 The compound represented by the formula (III) can be obtained as follows.

BC0X * + NCCH ₂ CN BC (0H) = (CN) (XI) (XII)

(Wherein, B is as defined above, X 'is a hydroxyl group, a halogen atom, 1 unique Mi Dazori Le group, 0 C 0 r ¹ or OS 0 ₂ represents an r ^2. R ^1, r ² is Each represents a lower alkyl group or a phenyl group which may be substituted.)

 That is, by reacting the compound represented by the formula (XI) with the malononitrile represented by the formula (XII) in an inert solvent in the presence of a base, the compound represented by the formula (1II) is obtained. The compounds represented can be obtained.

 The reaction is carried out by alkali metal hydroxides such as sodium hydroxide and hydroxylating hydroxide, carbonates such as sodium carbonate and potassium carbonate, triethylamine, diisopropyrethy. N, N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), THF, acetonitride in the presence of bases such as organic bases such as luminin, pyridine and imidazole. The reaction is carried out in a solvent such as lilyl, hexamyltrilinic acid triamide (HMPA), benzene, toluene, dichloromethane, or chloroform. Manufacturing method (ii)

N— N N— N OH

 base

 + BCOX "

 , N

 CN CN

 (IV) (V) (1 1 1)

(Wherein, A, B, R ¹ represents the same meaning as the X "is a hydroxyl group, a halogen atom, 1 -. Represents Lee Mi Dazori group, the 0 C_〇 r ³ or 0 S 0 ₂ r ^4. r ³ and r ⁴ are Each represents a lower alkyl group or an optionally substituted fu- nyl group. )

 That is, by reacting a compound represented by the formula (IV) with a compound represented by BC OX "in an inert solvent in the presence of a base, the compound represented by the formula (I) can be obtained. it can.

 The reaction is carried out by reacting 1 mol of the compound represented by the formula (IV) with 0.5 to 2 mol of the compound represented by BC〇X ”in the presence of a base in a solvent. The reaction is carried out using sodium hydroxide, alkali metal hydroxides such as hydroxylating hydroxide, sodium carbonate, carbonates such as calcium carbonate, triethylamine, diisopropyle. N, N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), THF, acetonitrile, hexamene in the presence of bases such as organic bases such as tilamine and pyridine. The reaction is carried out in a solvent such as trimethyl thiocyanate (HMPA), benzene, toluene, dimethyamine, and chloroform.

 The compound represented by the formula (IV), which is a raw material, is obtained by dissolving 1 mol of imidoyl chloride represented by the formula (II) and 0.5 to 2 mol of aluminum chloride such as aluminum chloride in a solvent. It can be obtained by reacting with 0.5 to 2 moles of malononitrile in the presence of sulfonic acid.

 (XII) (IV)

(In the formula, A, R ¹ and R represent the same meaning as described above.)

Solvents that can be used in the reaction include benzene benzene and 0-dichlorobenzene, and the reaction temperature is preferably from 100 ° C. to the boiling point of the solvent used. Manufacturing method (iii)

 1) (I)

(Wherein, A, B, and R ¹ have the same meanings as described above, and R ² represents a C i -s alkyl group, C,-

6 alkylcarbonyl group, C ₃ - S cycloalkyl group, ₆ an alkoxy carbonyl group, an alkylsulfonyl group, a substituted base may Nzoi group or an optionally substituted off We sulfonyl sulfonyl group, L Represents a halogen atom or the like. )

That is, by reacting 1 mol of the compound represented by the formula (I-11) with 0.5 to 2 mol of the compound represented by R ² L in an inert solvent in the presence of a base, The compound represented by (I) can be obtained.

 Examples of the base used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium carbonate such as sodium carbonate, carbonate carbonate, and the like. Organic bases such as lyethylamine, diisopropylpropylamine, pyridine and the like can be mentioned. Examples of the solvent include N, N dimethylformamide (DMF), dimethylsulfoxide (DMS〇), THF, acetonitrile, and hexamethylyltriamide (HMPA). , Benzene, toluene and the like can be used.

Examples of the alkylating agent or the acylating agent represented by R ² L include methyl iodide, thiolated iodide, propyl iodide, isopropyl iodide, butyl bromide, acetyl chloride, and benzoyl chloride. , P-toluenesulfonyl chloride, chloroformate ester and the like.

The compound (I) of the present invention may have a stereoisomer and a tautomer in some cases. All such forms are included in the scope of the present invention. In 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.

 (Insecticide · Acaricide)

 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 insecticidal, nymphalidic, larvicidal, and ovicidal action. The following are typical examples.

 Lepidopteran pests, for example, Spodoptera litura, Aedes aegypti, Tamanayaga, Aomushi, Yumanaginaba, Konaga, Cyanokoka Kummonamaki, Chiyamahamaki, Momomoinkiga, Pear Himeshinkyi, Mikanhamogoya Hosoga, Kinmonhosoga, Myimaga, Chadokuga, Nikkameiga, Kobunomeiga, Yoseki Biancon Borra-, Americana White Hitori, Sujimadara Meiga, Heliotis, Helicobelpa, Aggroti Genus, squirrels, squirrels, dolphins, insects, etc.

 Hemiptera pests, for example, peach aphid, mosquito aphid, Nisedai koa aphid, wheat bilea aphid, scorpion bug, beetle mosquito, yano enemy mosquito, kukonakaya maggot, onshikonajiramiko, tapa'ko Mi, pear lice, pear beetles, tobi-iron, hime-to-bin, sage-roonka, black-tailed tuna, etc.

 Coleoptera pests, for example, Leaf beetle, Leaf beetle, Korora beetle, Rice mud beetle, Black beetle, Azuki beetle, Bean beetle, Japanese beetle, Japrotica, Tobacco beetle, Japanese pine beetle Scarlet beetle, Sesame beetle, Agriotis spp.

 Diptera pests, for example, house flies, oak fly, sentinella flies, perfume flies, mikanko mipa'e, seeds', rice flies, key frogs, frog flies, and frogs , Net Thai Shima power, Shinahamadara power, etc.

 Hymenoptera pests, for example, southern blue thistle, Jerusalem artichoke, etc., Hymenoptera pests, for example, house mosquitoes, yellow hornets, power wasps, etc., straight-winged pests, for example, japonicus Panic cockroaches, red cockroaches, black cockroaches, horseshoe etc.

Isopteran pests, for example, house worms, mountain termites, etc. Lepidopteran insects, for example, human flea, lice, etc. Pests, for example, human lice, etc., mites, for example, Namihadani, Kanzahadani, Mandarin spider mite, Lingo spider mite

, Mikansavidanii, Lingosavidinii, Cyanofokolidani, Brevipalpas, G. tranicas, Robin's mite, Dermatophagoides farinae, Dermatophagoides farinae, O. tick ticks, Scarlet ticks, etc.

 Plant-parasitic nematodes, for example, sweet potato nematode, negusaresenchu, soybean cistocentrifuge, rice singarecentyu, matsunosaisenchu and the like.

 In addition, in recent years, many insect pests such as Japanese moth, pinworm, leafhopper, aphid, etc. have developed resistance to organic phosphorus agents, carbamates, and acaricides, causing a problem of insufficient efficacy of these agents. There is a need for agents that are effective against pests and mites of the strain. The compound of the present invention has excellent insecticidal and acaricidal activity against not only susceptible strains but also pests of organic phosphorus, carbamate or pyrethide resistant strains and mites of acaricide resistant strains. It is.

 In addition, the compound of the present invention is a highly safe drug with low phytotoxicity, low toxicity to fish poisons and warm-blooded animals.

 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.

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, that is, a wettable powder, a granule It can also be used in the form of powders, emulsions, aqueous solvents, suspensions, flowables and the like. When solid additives are used as additives and carriers, soybean grains, plant powders such as flour, diatomaceous earth, limestone, gypsum, talc, bentonite, pyrophyllite, clay And organic and inorganic compounds such as sodium benzoate, urea, and sodium sulfate. For liquid dosage forms, petroleum fractions such as kerosene, xylene, and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetate, triton Use chlorethylene, methyl isoptil ketone, mineral oil, vegetable oil, water, etc. as solvents. In order to obtain a uniform and stable form in these preparations, a surfactant should be used if necessary. It can also be added. The amount of the active ingredient is preferably 5 to 70% '. The wettable powder, emulsion and flowable thus obtained are diluted with water to a predetermined concentration to prepare a suspension or emulsion, and the powder and granules are used by spraying as it is . It goes without saying that the compound of the present invention alone is sufficiently effective, but it can also be used in combination with one or more of various fungicides, insecticides and acaricides, 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 :

Captan, Forpet, Thiuram, Ziram, Zineb, Maneb, Mancozeb, Provineb, Polycarbamate, Chlorotalonil, Kindzen, Capyahol, Iplodione, Procymidone, Vinclozori , Fluoroymid, Cymoxanil, Mepronil, Flutolanil, Pencyclone, Oxycarboxin, Josetylaluminium, Propamocarb, Triazimehon, Triazimenol, Propiconazole, Diclobutol Lazol, Vitelnor, Hexaconazole, Microcyl, Flusilazole, Ethaconazole, Fluotrimazole, Furtriaphen, Benconazole, Diniconazole, Cyproconazole, Cyproconazole Enari Mall, Tri Funoremizo , Prochloraz, imazalil, perfrazolate, tridemorph, fenpropimorph, trifoline, pthiobate, pyriphenox, anilazine, polyoxin, metalaxyl, oxazixil , Flalaxil, isoprothiolane, probenazole, pyrrolnitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate, benomyl, carbendazim , Thiophanemethyl, Himexazol, Basic Copper Chloride, Basic Copper Sulfate, Pentine Acetate, Triphenyltin Hydroxide, Jetfin Carp, Metasulfocarb, Quinomethioner , Pinapril, lecithin, baking soda, dithianon, zinocap, fenaminosulfur , Diclomethine, guazatine, dozine, IBP, edifamphos, mepanipirim, pharmazon, trichloramide, methasulfocarb, fluazinam, ethoxyquin, dimethomorph, pilokirone, tech Lof Yu Lam, Husalid, Penazin Oxide, Thiabendazol, Ulu Licyclazol, vinculozolin, simoxanil, cyclobynil, guazatine, propamocalp hydrochloride, oxolinic acid.

Insecticide · Acaricide:

Organophosphorus and carbamate pesticides:

 Phenthion, phenytrothion, diazinone, chlorpyrifos, ESP dothion, pentoto, dimethoate, formotion, marathon, trichlorfon, thiomethone, phosmet, dichlorvos, Acetate, EPBP, methyl parathion, oxydimethonmethyl, ethione, salicion, cyanophos, isoxathion, pyridaffunion, hosalon, methidathion, sulprophos, chlorphenvinphos, Trachlorbinfos, dimylbinphos, pro ,. Phos, isofenphos, ethylthiomethone, profenophos, pyraclophos, monochlorotophos, azinphosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, carbosulfan, benfracarb, flavocarpu Kisul, BPMCMTMCMIPC, Kyvallar, Pirimicarb, Etiofenkalp, Phenoxycarb, etc.

 Pyrethroid insecticides:

 Permethrin, Silmethrin, Delta Meslin, Fannolelet, Fenproha. Trin, pyrethrin, arrestrin, tetramethrin, resmetrine, dimethrin, propasrin, phenothrin, protoline, full ball line, Cyflutrin, cyhalothrin, full citrinate, ethoproprin, cycloprotrin, torametrin, silaflurin, profenprox, acrinatrin, etc. .

 Benzoyl Rare Other Insecticides:

Difluvenzuron, Chlorfluazuron, Hexaflumuron, Triflumuron, Tetrabenzuron, Funolefenoxuron, Funorescycloxuron, Buprofezin, Pyriproxyphen, Methyprene, Methoprene, Benzoeppine , Jafenthiuron, cecetamiprid, imidacloprid, nitenviram, fipronil, cartap, thiocyclam, bensultap, nicotine sulfate, rotenone, metaaldehyde, machine oil, machine oil, Microbial pesticides such as BT and insect pathogenic virus. Nematicide:

 Phenamiphos, phosthiazate, etc.

Acaricide:

 Chlorobenzylate, phenylisobromolate, dicophor, amitraz, BPPS, benzometholate, hexithiaxox, phenoxide oxide, polyactin, quinomethionate, CPCBS, tetra Radiofon, avermectin, milbemectin, clofenentine, sihexatin, pyrigben, phenpyroximate, tebufenvirad, pyrimidifin, fenochiocalp, Dienochlor and others.

Plant growth regulator:

Jibere Li emissions (such Jibere Li down A _3, Jibere re down A, Jibere Li down A ₇₎ IAA, NAA. BEST MODE FOR CARRYING OUT THE INVENTION:

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

Example 1

 a-[Hydroxy (2, 6-difluorophenyl) methylene] _ 1 -methyl-3-phenyl 2,4-triazoyl 5 -acetonitrile (Compound No. 2 Production of 1)

(a) 1 — Ciano — 2 ', 6' — Gifolo — 2 — Hydroxycin 2,6—Difluorobenzoic acid (2 g, 12.7 mmol) in 20 ml of THF was added to carbonitrile midiazole (CDI), 2.05 g (12.7 mm01) Was added under ice cooling, and the temperature was returned to room temperature, followed by stirring for 30 minutes. Again, cool on ice and add 0.83 g (12.7 mmo 1) of malonitol and 1.41 g (12.7 mm 01) of triethylamine successively and bring to room temperature. Returned and left overnight. The mixture obtained by concentrating the reaction solution under reduced pressure was diluted with an appropriate amount of ethyl benzenemonoacetate (1: 1), and washed with 5% aqueous hydrochloric acid (appropriate amount, 5 times) and water in that order. The organic layer was dried over magnesium sulfate and concentrated to obtain 1.71 g of a crystalline target compound.

Yield 65%

(b) a- [Hydroxy (2,6—difluorophenyl) methylene] 1-1-methyl-3—vinyl 2,4—triazo mono-5—acetonitrile (Compound No. 2-1)

 1 — cyano — 2 ', 6' — difluoro-1 2 — hydroxycinnamic ditriol 1.50 g (7.28 mm 0 1) and N—methyl p—toluenesulfonylbenzohydrazonoiruku mouth To a solution of 2.35 g (7.28 mm 0 1) of o-dichlorobenzene in 15 ml of dichlorobenzene, add 1.07 g (8.00 mm 0 1) of aluminum chloride, and then add 140 ° C. Heated at C for 30 minutes. After returning to room temperature, ice chips and black hole form were added, and the organic layer was separated. Subsequently, a 5% aqueous sodium hydroxide solution was added thereto, and the aqueous layer was separated. The crystals obtained by neutralizing the aqueous layer with concentrated hydrochloric acid were filtered to obtain 0.56 g of the desired compound. mp.194-196 ° C yield 23% Example 2

3 — Hydroxy-1 3 — (5 — Krollo 1 — Methiru 3 — Trifluorometylpyrazol 4 — yl) — 2 — (1 Methyl — 3 — Phenyl triazolo 5 — Y Preparation of 2- (2-propene) trile (Compound No. 4-11)

5 — Cyanomethyl-1 1-methyl-1 3 —Phenyltriazole 0.67 g (3.38 mm01) is dissolved in benzene 7 m1 and triethylamine is dissolved under ice-cooling. 0.5 2 ml (3.73 mm 0 1), 4 — dimethylaminoaminopyridin 0.1 g, and 5 -chloro 1 -methyl 3-trifluorometyl pyrazole 4 -carbonyl 0.92 g (3.72 mm 01) of lid was sequentially added, and the mixture was heated at 50 ° C. After washing the reaction solution with water, a 10% aqueous sodium hydroxide solution was added, the separated aqueous layer was acidified with concentrated hydrochloric acid, and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to obtain 0.67 of the desired compound. 11.189-191 ° C

Yield 49% Example 3.

α— [Methoxy (2,6—difluorophenyl) methylene] —1—Methyl-3—Phenyl—1,2,4-triazole—5—Acetonitrile (compound Production of number 3 —)

a-[Hydroxy (2, 6-difluorophenyl) methylene] 1 1-Methyl 3-Phenyl 1, 2, 4-Triazole 5-Acetonitrile 0.5 g (1.47 mm 0 1) in 5 ml of methylene chloride in trimethyloloxonium tetrachloride 0.24 g (l. 62 mmo1) of chloroform was added, and the mixture was stirred at room temperature for 3 days. A 10% aqueous sodium carbonate solution was added to the reaction solution, and the organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated to obtain 0.40 g of a crystalline target compound. . mp. 19 1-19 4 ° C Yield 7 7% Example 4

 a-[Acetoxy (2, 6-difluorophenyl) methylene] 1-1 -methyl-3-phenyl-1, 2, 4-Triazo-1-5-acetonitrile (Compound No. 3-1 2) Manufacturing

a-[Hydroxy (2, 6-difluorophenyl) methylene] 1-1 -methyl-3-phenyl-1, 2, 4-1 triazo-5-acetonitrile 0.2 1 g (0.62 mm 01) in 3 ml of methylene chloride in 0.1 ml of triethylamine (0.72 mm 01) and 0.05 ml of acetyl chloride (0.70 mm) mm ol) were added sequentially at −20 ° C. The reaction solution was returned to room temperature, water was added, the organic layer was separated, dried over magnesium sulfate, and concentrated. The obtained mixture was purified by silica gel column chromatography (developing solution 1: 2 ethyl acetate-n-hexane) to obtain 0.102 of the desired compound. 11113.1 5 8-1 60 0 Yield 4 3% Reference Example 1

 5 — Cyano methyl 1-1 methyl 3-Manufacture of vinyl triazole

(a) Preparation of 5-bromomethyl-1-methyl-3- 3-phenyl triaryl

 N—Methyl-p—Toluenesulfonylbenzohydrazonoyl lip mouth 14.7 g (45.5 mmol) and promorecetonitrile 6.45 g (53.8 mmo1) o — 14.5 g (54.2 mm 01) of aluminum bromide was added to a solution of 5 O ml of benzene with dichloro mouth, and the mixture was heated at 140 for 30 minutes. After returning to room temperature, ice chips and black hole form were added, and the organic layer was separated and dried over magnesium sulfate. The solution obtained by filtering magnesium sulfate was purified by silica gel column chromatography (developing solution 1: 2 ethyl acetate-hexane) to obtain 6.04 g of the desired compound. Yield 5 3%

(b) 5—Production of cyanomethyl 1-methyl-3_phenyltriazole

 5—Bromethyl-1—Methyl-3—Phenyltriazole A solution of 6 g (23.8 mmo 1) of dimethyl sulfoxide in 60 ml of 1.7 ml of potassium hydrocyanate was added. 4 mm 01) was added and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction solution, extracted with ethyl acetate, the organic layer was washed with water (three times), dried over magnesium sulfate, and concentrated under reduced pressure. The obtained mixture was purified by silica gel column chromatography (developing solution 1: 1 ethyl acetate-n-hexane) to obtain 2 g of the desired compound. Yield 4 2% Reference Example 2

 5 — Sharp methyl 1 — Meltyl 3 — (2-Fluorophenyl) triazole

(a) 3 — Cyanomethyl 5 — (2 — Fluorophenyl) triazole

60 ml of methanol in which 1.33 g (33. 3 mmol) was dissolved was cooled with ice, and ethyl 2-fluorobenzimidetrate hydrochloride 6.75 g (33.2) mol) and And 3.39 g (34.2 mmo 1) of cyanoacet hydrazide were sequentially added at room temperature, followed by heating under reflux for 2 hours. After returning the reaction solution to room temperature, it was concentrated under reduced pressure. Ethyl acetate and water were added to the obtained mixture, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crystalline compound was washed with chloroform to give 2.94 g of the desired compound.

 Yield 43.9%

 (b) Production of 5-cyanomethyl 1-methyl 3- (2-fluorophenyl) triazole

3 — cyanomethyl 5 — (2 — fluorophenyl) triazole 5 g (24.8 mm 01) is dissolved in N, N — dimethylformamide 50 ml and 60% 0.99 g (24.8 mm 01) of sodium hydride (oil-based) and 4.22 g (29.7 mm 01) of methyl iodide are added sequentially under ice-cooling. Return to room temperature. Ice water and ethyl acetate were added to the reaction solution, the organic layer was separated, dried over magnesium sulfate and concentrated. The obtained crystalline compound was washed with ether and chloroform to give 1.3 g of the desired compound. Yield 21% Tables 2 to 7 show the structural formulas and physical properties of the compounds of the present invention including the above Examples.

Compound number A Yn R, physical constant *

 2 1 1 P h 2, 6-F, Me [194-196]

2-2 P h 2, 6-F, E t [150-153]

2-3 P h 2, 6-F, n Pr [139-142]

2-4 P h 2, 6-F, i Pr [190-195]

2-D P h 2, 6-F, n He x [107- 1 10]

2-6 P h 2, 6-F, P h [197-199]

2-7 P h 2, 6-F, g 3 [164-166]

2-8 2 -C 1-P h 2, 6-F., Me [226-228]

2-9 3 -C 1 -P h 2. 6-F, Me [169-170]

2- 10 4-C 1 -Ph 2, 6-F, Me [248-249. 5]

2- 1 1 2-F-Ph 2, 6-F, Me [245-246]

2- 12 3-F-Ph 2, 6— F, Me [140- 142]

2- 13 4-F-Ph 2, 6-F., Me [88-90]

2- 14 2— C 1 1 6— F— Ph 2, 6-F, Me [174-175]

2- 15 4-C F,-P h 2. 6-F, Me [95-971

2- 16 4 One OCF: Ph 2, 6-F, Me [153-1 55]

2- 1 7 4-P h-P h 2, 6-F, Me [248-250]

2- 18 P h 2— C 1 Me [184-186]

2- 19 2— M e— P h 2-C 1 Me [171-173]

2-20 P h 3-C 1 Me [178-182]

2-2 1 P h 4— C 1 Me [190-191]

2-22 P h 3, 4-C 1, Me [207-210]

2-23 Ph 2-F Me [83-90]

2-24 P h 2— C 1 1 6— F Me [170-172]

: Melting point, or n _D : refractive index. same as below Table 2 (continued) Compound number A Yn R> Physical constant *

 2-25 P h 4 1 C I 1 2— NO., Me [225 (decomposition) 1

2— 26 P h 4 OMe Me [216-2 18]

2-27 P h 4 1 OP h Me [173-1 74]

2-28 P h 2— CF _{: i} Me [198-200]

2-29 P h 2-C F E t [189-191]

2-30 P h 2-CF _{: in} Pr [89-92]

_{2- 31 P h 2 - CF:} ! I P r [1 1 1 - 1 13]

2-32 P h 2-CF _{: i} n H ex [78-81]

2-33 P h 2-CF _{: i} g 3 [159-162]

2-34 4-C 1-P h 2-CF _{: f} Me [184. 5-186]

2-35 4-P h-P h 2— C F M e [230-232]

2-36 P h 2-CF _{; i} Me [157-159]

2-37 P h 4 -M e Me [154-157]

2-38 P h 2 - F - 6 - CF:, M e [209 - 21 1]

2-39 t B u Me [153-154]

2-40 t B u 2, 6-F, Me [141-143]

2-41 t B u 4 1 C 1 Me [1 16- 1 18]

2-42 c Pen 2.6-F, Me [153-155]

2-43 g 1 2, 6-F, Me [188-191]

Table 3

 * 1: E or Z body

* 2: EZ mixture

* NMR: NMR data is shown in Table 7. same as below Table 4 (continued)

Table 4 (continued)

 * 3: EZ mixture

* 4: E or Z body

Table 5

Compound physics te number

 5 1 1 Me C F, C 1 r l Q a Q

5-2 Me Br C 1 Me amo rphous * ^NMR

5-3 Me C 1 H Me [220-22 1]

5 -4 M e H C 1 Me (2 1 0- 2 1 1.5)

5-5 Me C 1 C 1 Me [1 83-1 8 5]

5-6 Me CF _{: f} H Me [204-206]

_{5 - 7 Me CF:! HE} t [1 82 - 1 83]

5-8 Me CP :, H n Pr [1 58-1 59]

5-9 Me C F, Hi Pr [1 65-1 66]

5-10 Me CF _{; i} H n H ex amo rphous * ^NMK

5-1 1 Me H CF, Me [1 7 1-1 73]

5-1 2 Me CF _{: 1} F Me [1 99. 5-202]

5-1 3 2-F n Pr CF _{: f} F Me [1 2 8-1 29]

5-1 4 Me SMe H Me [234-236]

Table 6

Table 7 NMR data Compound number ^ -NM (C D C 1, .δ p pm)

 4—1 4 3.97 C3H, s), 4.20 (3Η, s), 7.05—7.12 (4Ηm), 7.20 (1Η,

 J = 7 Η ζ, t 7.41 (2 Η, J = 7 Η ζ, t), 7.88 (2 Η, J = 7 Η ,, d)

4—1 7 1.60 (3Η, J = 7Η, t) .4.47 (3Η, s), 4-6 1 (2Η, J ^ = 7Η, ¾)

 7.50-7.70 (3 Η, m), 7.89-7.97 C2 H, m)

 4-2 6 0 9 0 (Η Τ — 7 Η 7 t) 1 2 'ϊ-1 8 0 ((6 Η m) 1 9 0— 0 5 (2 Η

 1.54 (2 HJ = 7 Hz, t), 7.25-7.35 C2 H, m), 7.50-- 7.60 C1H, m), 8.02- 8.1 0 (1 H, m)

 4-4 3 0.88 (3 H, J = 7 Hz, t). 1.25-1.50 (6 H, m), 1.90-2.05

 (2 H m), 4.56 (2 H, J = 7 H z, t), 7.08-7.16 (2 H, m), 7.46-111

 4 — 5 0 1.80 (6H.ms), 3.91 (3Hs), 4.12 (3H, s), 7.28—7.42

 (5 H, m)

 4-6 1 1 .07 a n d 1.17 (t o t a l 3 H, J = 7 H z, 2 t), 1.5 3-1.63 (2 H, m),

 V1 ώ d n a. Ov ΐ on, T ——i ι z, n, 0. 0 1 d ii u. U 1

 (total 3 H, 2 s), 4, 3 2— 4.49 (2 H, m), 7.15-7.25 (2 H, m), 9 7 4 C 1 H m) 7 7 c; — 7 R and 7 QR— R Ω 4 ft 0 ta

 (1 H, 2 m)

 4-6 2 1.06 and 1.38 (total 9 H, 2 s), 1.5 1 — 1.64 (3 H m), 3.82 and 4 09 (tntn \? Σ ) 4 3 2— 4 4 5 (2 H m) 7 1 5— 7 2 5

(2 H, m), 7, 35-7.42 (1 H, m), 7.75-7.85 a nd 8.00-8.008

(t o t l 1 H, 2m)

 1.08 an cl 1.39 (total 9 H, 2 s), 3.85 and 4.00 (total 3 H, 2 s), 4.09 (3 H. s), 6. 9 1 — 7.04 (2 H. m), 7.32-7.43 (1 H, m)

4-6 5 0.9.5-1.23 (4 H, m), 1.62-1.93 (1 H, m), 3.8 4 3.98, 4.08 and 4.09 (total 3 H., 4 s), 6.90-7.05 (2 H, m), 7.29-7.42 (1 H m)

 4-6 7 1.09, 1, 20, 1-5 a n d 1.37 (t o t a l 18 H, 4 s), 3.92 (3 H, s),

 4.00 (3 H, s)

 4-7 0 1.11 (9 H, s), 1.26-1.29 (10 H, m) .3.93 (3 H, s), 4.00

(3 H, s) L 8

 (^ Course) one ^ "awN

S0Zl0 / 86df / 13J £ 89h / 86 OM (Insecticide and acaricide)

 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, but can be changed in a wide range. Parts in Formulation Examples are parts by weight.

Example 5 wettable powder

 Compound of the present invention 40 parts

 Diatomaceous earth 5 3 parts

 Higher alcohol sulfate 4 parts

 Alkyl naphthalene sulfonate 3 parts

 If the above are uniformly mixed and finely pulverized, a wettable powder with an active ingredient of 40% is obtained. Example 6 Emulsion

 Compound of the present invention 30 parts

 Xylene 3 3 parts

 Dim Chilholm Amid 30

 Polyoxyethylene alkyl ether 7 parts

 By mixing and dissolving the above, an emulsion containing 30% of the active ingredient is obtained.

 Example 7 Dust

 Compound of the present invention 10 parts

 Talc 8 9 parts

 Polyoxyethylene alkyl ether 1 part

 If the above are uniformly mixed and finely pulverized, a powder containing 10% of the active ingredient is obtained. Example 8 granules

 5 parts of the compound of the present invention

 Cray 7 3 copies

 Vento Night 20

 Dioctyl sulfosac cine sodium 1 part

 1 part of sodium phosphate

The above is pulverized and mixed well, water is added and kneaded well, and the mixture is granulated and dried to obtain granules of 5% of active ingredient. Example 9

 Compound of the present invention 10 parts

 Sodium ligninsulfonate 4 parts

 1 part of sodium dodecylbenzenesulfonate

 Kisanta Ngam 0.2 parts

 Water 84.8 parts

 The above ingredients are mixed and wet-pulverized until the particle size becomes 1 micron or less, whereby a suspension containing 10% of the active ingredient is obtained.

【The invention's effect】

 The effect of the compound of the present invention was confirmed by the following test. The following compounds were used as control compounds in addition to the known insecticides.

A: B:

A is a compound of No. V-31 in Table 19 of WO97Z40009, and B is a compound exemplified in Table 10 of WO97 / 40009. Test Example 1 Efficacy against aphalt

 According to the formulation of the wettable powder described in Example 5 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 and air-dried. The leaves were put into a petri dish containing five second instar larvae. They were covered with a glass lid and placed in a thermostatic chamber at a temperature of 25 ° C and a humidity of 65%. Two iterations. As a result, the compounds with the following numbers showed an insecticidal rate of 100%. Although chlordimeform used as a control was 40%, A and B did not show any insecticidal activity.

2-1, 2-2, 2 3, 2-4, 2-5, 4-1 8, 4-1, 9, 4-2 8, 4-3 4, 5-1 3 Test example 2

 A 10-day-old germinated cucumber seeded in a three-dimensional bowl was inoculated with an adult Aphid aphid. One day later, the adults were removed, and the larvae parasitic on the nymphs were diluted with water to a compound concentration of 125 ppm according to the emulsion formulation described in Example 6 of the above-mentioned drug. The chemical was sprayed. They were placed in a thermostatic chamber at a temperature of 25 and a humidity of 65%, and the insecticidal rate was examined after 6 days. The test is in duplicate. As a result, the compounds with the following numbers showed an insecticidal rate of 100%. In addition, chlordimeform used as a control showed an insecticidal rate of 55% and A shows an insecticide rate of 83%, but B did not show any insecticidal activity.

 2-1, 2-2, 2-9, 2-1, 1, 2-1, 2, 2-13, 2, 2-18, 4, 2-2, 3-2, 3-3, 3- 3-4, 3-5, 3-6, 3-7, 3-8, 3-1 9, 3-1 0, 4-1 1, 4-1 3, 4-1 4, 4-1 6, 4-10, 4-1 7, 4 1 7, 4 1 8, 4 1 2 1, 4-2 2, 4 1 2 3, 4 1 2 5, 4 1 2 5, 4-2 7, 4-2 9, 4 1 3 2, 4 1 3 4, 4 1 3 5, 4 1 3 8, 4 1 4 4, 4 1 5 6, 4 1 6 0, 4 1 6 1, 4 1 6 2, 4 1 6 3, 4 1 6 4, 4 1 6 5, 4 1 6 6, 4 7 0, 5-2, 5-4, 5-5, 5-6, 5-1, 2-5-1 3

 Test Example 3 Efficacy against Namihadaji

 Seventeen adult females of Nami-nadani, resistant to organophosphates, were inoculated on the first true leaf seven to ten days after the germination of the kidney seeds sown in two-inch pots. According to the formulation of the hydrating agent shown in Example 5, a chemical solution diluted with water was sprayed so that the compound concentration became 125 ppm. After being placed in a constant temperature room at a temperature of 25 and a humidity of 65%, the adults were removed 3 days after spraying, and eggs that were laid during these 3 days were checked on day 1 to see if they could develop into adults. The mite killing effectiveness was determined. The acaricidal effectiveness was determined by the following equation. Untreated larvae count-treated larvae count

 Acaricidal effectiveness (%)-l o o

 As a result, the compounds with the following numbers exhibited acaricidal activity of 100%. Chlordiformol used as a control was 55%, A was 98%, and B was 29%.

 4-1 1, 4-1 2, 4-1 3, 4-1 4, 4-1 5, 4-1 6, 4-1 7, 4-1 8, 4-1 9

, 4-1 10, 4-1 1, 4-1 3, 4-1 7, 4 1 1 8, 4 1 1 9, 4 1 2 0, 4-1 2 1, 4-1 2 2, 4-1 2 3, 4—2 4, 4-1 2 5, 4 1 2 6, 4 1 2 8, 4 1 3 0, 4 1 3 1, 4 1 3 9, 4-1 40, 4-1 41, 4-1 42, 4-1 43, 414, 415, 416, 414, 417, 418, 419, 4 1 5 1, 4-5 2, 4-5 3, 4 1 5 6, 4 1 5 7, 4 1 5 8, 4 — 5 9, 4 1 6 0, 4 1 6 1, 4 1 6 2, 4 1 6 3, 4 1 6 4, 4 1 6 5, 4 1 6 7, 4 — 6 8, 4 1 6 9, 4 1 7 0, 4-7 1, 5-2, 5-5, 5- 6, 5-1 2, 5-1, 3, 6-1, 6-1 6

 Test example 3 Efficacy against red mites

 Eight female adults of the drug-sensitive spider mites were inoculated into the leaves of the mites placed in the dish. According to the wettable powder formulation shown in Example 5, a fixed amount of a chemical solution diluted with water was sprayed by a rotary spray tower so that the compound concentration became 125 ppm. Placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65%, the adults were removed 3 days after spraying, and the larvae that hatched from the eggs laid during these 3 days were examined on the 7th day for viability and killed. Mite effectiveness was determined. The acaricidal effectiveness was determined by the following equation.

Untreated larvae count-treated larvae count

 Acaricidal activity (%) = ~ ~~ "~ X 100 Number of untreated larvae As a result, the compounds with the following numbers showed an acaricidal efficacy of 100%. Tetradiphone was 58%, A was 78%, and B was 3%.

 2-3 0, 4-1 1, 4-1 2, 4-1 3, 4-1 4, 4-1 5, 4-1 6, 4-1 7, 4 — 8, 4-1 9, 4-1 1 0, 4-1 1 1 , 4-1 3, 4 -1 7, 4 -1 8, 4-19, 4 1 2 0, 4 1 2 1, 4 1 2 2, 4 1 2 3, 4 1 2 4, 4 1 2 5 , 4-26, 4-128, 4-130, 4-131, 4-139, 4-140, 4-141, 4-142, 4-143, 4-144 , 4-145, 4-146, 4-147, 4-148, 4-149, 4-51, 4-52, 4-153, 4-56, 4-57 , 4-158, 4-159, 4-1600, 4-16-1, 4-2, 4-163, 4-164, 4-165, 4-167, 4-168 , 4-169, 4-1700, 4-71, 5-2, 5-3, 5-12, 5-13, 6-1, 6-5, 6-6

Claims

1. General formula (I)

Ν

Special

[In the formula, A, ₆ alkyl group, C ₂ - ₆ alkenyl group, C ₂ - ₆ alkynyl group, C 3 -8 cycloalkyl group, (halogen atom, a nitro group, Shiano group, C ie Al kill group, ., - _beta haloalkyl group, _e alkoxy group, may be substituted by _haloalkoxy group) Fuweniru group, wherein

 ί car

R ³ (R ⁵ ) n

(In the formula, R ³ and R ⁴ are a hydrogen atom or an alkyl group, R ⁵ is the same or different and is a halogen atom, a nitro group, a cyano group, a ア ル キ ル alkyl group, a d-fihaloalkyl group, and n is 0 or 1 represents an integer of 5) with a benzyl group represented, or, (halogen atom, _alkyl group, -. ₆ haloalkyl group, ₆ alkoxy group, C, - be substituted by _e alkylthio group Good) represents a heterocyclic group, and the heterocyclic group represents a pyridyl group, a pyrazolyl group, a furyl group, a phenyl group, a benzoyl group or a benzofuranyl group.

The B (halogen atom, a nitro group, Shiano group, C _i-6 alkyl group, d one Haroa alkyl group, C _i-6 alkoxy group, an alkylthio group, C -! May be substituted with _e haloalkoxy group ) Fuweniru group, (halogen atom, a nitro group, Shiano group, C, - ₆ alkyl group, C, - _e haloalkyl group, ₆ alkoxy group, C -! may be substituted with Al Kiruchio group) the heterocyclic group And a heterocyclic group is a pyridyl group, a pyrazolyl group, a furyl group, a chenyl group, a thiazolyl group, or 1,2,3-thia Represents a diazolyl group.

R ¹ is _alkyl group, d - ₆ haloalkyl group, ₆ alkoxy C i-6 Ryo alkyl group, phenyl group, C ₃ - ₈ cycloalkyl group, C ₃ - ₈ cycloalkyl ₆ alkyl group, C ₂ - ₆ alkenyl groups, C ₂ - (i alkynyl, C ₂ - ₆ haloalkenyl group, C ₂ -! 6 haloalkynyl group, C _l-6 alkyl group, C -6 alkoxycarbonyl alkylsulfonyl Ji Bok B alkyl group, Application Benefits C i — β alkylsilyl represents a C 1-6 alkyl group.

R ² represents a hydrogen atom, d- _β alkyl group, COR ^G , C, -c alkylsulfonyl group or phenylsulfonyl group, and R ⁶ represents a C! -6 alkyl group, phenyl group, phenyl group ^ alkyl group, Fuwenokishi d -6 alkyl group, C ₃ - _beta a cycloalkyl group, an _C6 alkoxy group, may be substituted with a halogen atom pyridyl group, full drill group or Choi two Le group. ] The compound represented by these.

 2. General formula (II)

A-C (C 1) = NN (R ^] ) R (II)

(Wherein, A and R ¹ have the same meanings as in claim 1 and R represents a phenylsulfonyl group or a C, -6 alkylsulfonyl group which may have a substituent.) Compound and general formula (III)

B— C (OH) = C (CN) ₂ (III)

 (Wherein, B has the same meaning as in claim 1). A compound represented by the general formula (I-11)

N

(Wherein, A, B, and R ¹ have the same meanings as in claim 1).

3. General formula (IV)

N

(Wherein, A and R ¹ have the same meanings as in claim 1).

(V)

 B-C〇 C 1 (V)

 (Wherein B has the same meaning as in claim 1). The general formula (I-11)

N

(Wherein, A, B, and R ¹ have the same meanings as in claim 1).

 4. General formula (I-1)

(Wherein A, B, and R ¹ have the same meanings as in claim 1), and a compound represented by the general formula (VI):

R ² -L (VI)

(Wherein, R ² is an alkyl group, C, - ₆ alkyl group, C ₃ - ₆ cycloalkyl group, C _i-6 alkoxycarbonyl group, ₆ alkylsulfonyl L represents a phenyl group, a benzoyl group which may be substituted or a phenylsulfonyl group which may be substituted, and L represents a halogen atom. Wherein the compound represented by the general formula (I) is reacted with

(Wherein, A, B, R ¹ , and R ² have the same meanings as in claim 1).

5. General formula (I)

(Wherein, A, B, R ¹ and R ² have the same meanings as in claim 1.) An insecticide characterized by containing one or more of the compounds represented by the formula (1) as an active ingredient. Acaricide