JP2000290279A - Acrylonitrile compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new acrylonitrille compound capable of exhibiting an excellent pest control activity and useful as a new insecticide or a new germicide. SOLUTION: This acrylonitrile compound is represented by formula I (A is a 1-6C alkyl, a 2-6C alkenyl or the like; R1 is H, a 1-12C alkyl, a 2-12C alkenyl or the like; R2 is H, a 1-4C alkyl, a 2-4C alkoxyalkyl or the like; R3 is a 1-4C alkyl, a 2-4C alkenyl, a 1-4C haloalkyl or the like; R4 and R5 are each H, OH, SH, NH2, a halogen, a 1-4C alkyl or the like), e.g. 3-(1,4- dimethylpyrazol-5-yl)-3-hydroxy-2-(1-methyl-3-phenyl-1,2,4-triazol-5-y l)-acrylonitrile. The compound represented by formula I can be obtained by reacting a cyanomethyltriazole derivative represented by formula II with a carboxylic acid derivative represented by formula III (L1 is a leaving group) in the presence of a base and further reacting the resultant compound with a compound represented by formula IV (L2 is a leaving group).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel acrylonitrile compound and an agricultural chemical containing the compound as an active ingredient. The pesticides in the present invention are insecticides, acaricides, nematicides, herbicides, fungicides, and the like, and are particularly insecticides, acaricides, and nematicides in the fields of agriculture, horticulture, livestock, and sanitation. .

[0002]

2. Description of the Related Art Acrylonitrile derivatives as pesticides are described in WO97 / 40009 and WO98 / 42683.

[0003]

With the long-term use of insecticides and fungicides, pests have recently acquired resistance,
Control with conventional insecticides and fungicides has become difficult.
Therefore, an object of the present invention is to provide a novel insecticide or fungicide exhibiting excellent pest control activity.

[0004]

Means for Solving the Problems The present inventors have continued their studies to solve the above-mentioned problems, and as a result, have found that the following compounds exhibit excellent pest control activity, and have completed the present invention.

That is, the present invention relates to the compounds described in the following [1] to [5] (hereinafter, referred to as the compounds of the present invention) and the agrochemicals containing the compound described in the following [6] as an active ingredient. is there.

[1] Equation (1):

[0007]

Embedded image

[Wherein A is C₁~ C₆Alkyl, C_Two~ C₆Al
Kenil, C₁~ C₆Haloalkyl, C₁~ C_FourSubstituted with alkyl
May be C_Three~ C₇Cycloalkyl, substituted with X
Phenyl, naphthyl or pyridinyl
R¹Is H, C₁~ C₁₂Alkyl, C_Two~ C₁₂Alkenyl, C₁
~ C₁₂Haloalkyl, C₁~ C_FourSubstituted with alkyl
Good C_Three~ C₇Cycloalkyl, C_Two~ C₁₂Alkylsulf
Phenylalkyl, C_Two~ C₁₂Alkylsulfinylalkyl
, C_Two~ C₁₂Alkylsulfonylalkyl, C_Two~ C₁₂A
Lucoxyalkyl, C substituted with phenyl₁~ C _ThreeArchi
Phenyl optionally substituted with X, COORa, CONHR
b, CONRaRb, CORa or CO (N-piperidinyl), R^Two
Is H, C₁~ C_FourAlkyl, C_Two~ C_FourAlkoxyalkyl, CH_Two
SCH_Three, CH_TwoOC_TwoH_FourOCH_Three, C substituted with Rc or Rd₁~ C_Four
Alkyl, tetrahydropyranyl, trimethylsilyl,
SO_TwoRe, SO_TwoNHRb, SO_TwoNRaRb, C (S) NHRb, C (S) NRaRb, CH_Two
CO_TwoRa, C (O) Rf, P (O) RgRh, P (S) RgRh, alkali metal,
An alkaline earth metal or NHRiRjRk,

X is halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁
-C ₄ haloalkoxy, C ₁ -C ₄ alkoxyalkyl, C ₁ ~
C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ ~
C ₄ haloalkylsulfonyl, 1 to 3 substituents arbitrarily selected from NO ₂ , CN, phenyl and phenoxy, wherein R ⁴ and R ⁵ are each independently H, OH, SH, NH ₂ ,
Halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄
Haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkoxyalkyl, C ₁ -C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfenyl, C ₁ ~
C ₄ haloalkylsulfinyl, C ₁ -C ₄ haloalkyl sulfonyl, an NO ₂ or CN, R ³ is C ₁ -C ₄ alkyl, C
₂ -C ₄ alkenyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxyalkyl,

Ra is C ₁ -C ₆ alkyl, Rb is H, C ₁ -C
₆ be substituted with alkyl or T ¹ is also phenyl, Rc is halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ ~ C ₄ haloalkoxy, C ₁ -C ₄ alkoxyalkyl is a phenyl optionally substituted with one or more selected from among, Rd is halogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkoxy which may be benzoyl substituted with at least one selected arbitrarily from among alkyl , Re is phenyl optionally substituted by C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₁ -C ₄ haloalkyl or T ^1,

Rf is C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl,
C ₁ -C ₆ haloalkyl, C ₂ -C ₄ alkoxyalkyl, C ₃ ~
C ₆ halocycloalkyl alkyl, C substituted with Rc ₁ -C ₄ alkyl, C ₁ -C optionally substituted by _alkyl C ₃ -C ₇ cycloalkyl, substituted with Rc and C ₁ -C ₄ alkyl cyclopropyl, Rc and C ₃ -C ₄ cycloalkyl substituted with halogen, T ² and C ₁ -C ₄ alkyl substituted cyclopropyl, C ₂ -C ₄ alkenyl substituted with Rc, C ₁ ~ C ₆ alkoxy, C ₁ -C ₄ haloalkoxy, C ₂ -C ₅ alkenyloxy, C ₁ -C ₄ alkyl optionally substituted C ₃ even though -C ₆ cycloalkoxy, benzyloxy, COORa, -NU ¹ U ^2, T ³
In phenyl optionally substituted, naphthyl, pyridinyl, or phenyl C ₁ -C ₆ alkyl optionally substituted with T ^1, Rg and Rh are each independently, OH, C ₁ -C ₆ alkyl,
C ₁ -C ₆ alkoxy or C ₁ -C ₄ alkylsulfenyl,

[0012] Ri, the Rj and Rk are each independently, H, phenyl and C ₁ -C ₆ alkyl, C ₁ -C ₄ alkenyl, C ₁ -C ₄ alkenyloxy, substituted by C ₁ -C ₃ alkyl Good C ₃
-C ₆ or cycloalkyl or benzyl, or
Two of Ri, Rj and Rk may form a 5- to 8-membered ring group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is attached,
T ¹ is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl or C ₁ -C ₄ alkoxy, T ² is a good C ₂ -C ₄ alkenyl optionally substituted by halogen,

T ³ is halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄
Haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkyl scan phenyl, C ₁ -C ₄ alkyl Sufi alkylsulfonyl, C ₁ -C ₄ alkyl scan sulfonyl Le, C ₁ -C ₄ haloalkyl scan phenyl, C ₁ -C ₄ haloalkylsulfonyl Sufi alkylsulfonyl, C ₁ -C ₄ haloalkyl _{sulfonyl, nO 2, CN, CHO,} -NU 1 U 2, to 1 are arbitrarily selected from among phenyl and phenoxy 5
U ¹ and U ² are each independently H, C ₁
A 5- to 8-membered ring group which represents -C ₆ alkyl, COORa, phenyl or benzyl, or may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which U ¹ and U ² are bonded May be formed. An acrylonitrile compound represented by the formula:

[2] A is phenyl and R ¹ is C ₁ -C ₆
Alkyl, R ² is H or C (O) R f, and R ³ is C ₁ -C
₆ alkyl, R ⁴ is H, halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy, R ⁵ is H or C ₁ -C ₆ alkyl, R f is C ₁ -C ₆ alkyl The acrylonitrile compound according to the above [1], which is:

[3] R ¹ is methyl or normal hexyl, R ³ is methyl, R ⁴ is H, chlorine atom, methyl or methoxy, R ⁵ is H, methyl or ethyl, and Rf is The acrylonitrile compound according to the above [2], which is tertiary butyl.

[4] A is phenyl, and R ¹ is C ₁ -C ₆
Alkyl, R ² is H or C (O) R f, and R ³ is C ₁ -C
₆ alkyl, R ⁴ is H, halogen or C ₁ -C ₆ alkyl, R ⁵ is H or C ₁ -C ₆ alkyl, Rf is C ₁
~C is a ₆ alkyl above [1] acrylonitrile compounds described.

[5] R ¹ is methyl or normal hexyl, R ³ is methyl, R ⁴ is H, chlorine atom or methyl, R ⁵ is H or methyl, Rf is tertiary butyl A certain acrylonitrile compound according to the above [4].

[6] An agricultural chemical comprising at least one of the acrylonitrile compounds according to [1] to [5] as an active ingredient.

[0019]

BEST MODE FOR CARRYING OUT THE INVENTION -C (C
The N) = C (OR ² ) — moiety has two isomers, E and Z, when R ² is other than a hydrogen atom, both of which are included in the present invention. When R ² is a hydrogen atom, there are tautomers, which are also included in the present invention.

Next, A, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Ra, Rb,
Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, T 1, T 2, T 3, U 1
And preferred ranges of U ² will be described.

Preferred ranges of A are the following groups.
That, AI: C ₁ ~C ₆ alkyl, optionally substituted with X phenyl, naphthyl or pyridinyl. AII: C ₁ ~C ₆ alkyl, phenyl optionally substituted by X.

Preferred ranges of R ¹ are the following groups.
R ¹ I: H, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkylsulfenylalkyl, C ₂ -C ₁₂ alkoxyalkyl, C ₁ -C ₃ alkyl substituted with phenyl. R ¹ II: H, C ₁ -C ₁₂ alkyl.

Preferred ranges of R ² are the following groups.
R ² I: H, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkoxyalkyl,
CH ₂ OC ₂ H ₄ OCH ₃ , SO ₂ Re, SO ₂ NHRb, SO ₂ NRaRb, C (S) NHRb,
C (S) NRaRb, CH ₂ CO ₂ Ra, C (O) Rf, alkali metal, alkaline earth metal, NHRiRjRk. R ² II: H, C ₁ -C ₄ alkyl, C ₂
-C _{4 alkoxyalkyl, SO 2 Re, C (O} ) Rf, alkali metals, alkaline earth metals, NHRiRjRk. _{^{R 2 III: H, C 1}} ~C 4 alkyl, C ₂ -C _{4 alkoxyalkyl, SO 2 Re, C (O} ) Rf.

Preferred ranges of R ³ are the following groups.
R ³ I: C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxyalkyl. R ³ I
I: C ₁ ~C ₄ alkyl.

Preferred ranges of R ⁴ are the following groups.
^{R 4 I: H, OH,} SH, NH 2, halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkoxyalkyl. R ⁴ II: H, OH, halogen, C ₁ -C ₄ alkyl.

Preferred ranges of R ⁵ are the following groups.
^{R 5 I: H, OH,} SH, NH 2, halogen, C ₁ -C ₄ alkyl, C ₁
-C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkoxyalkyl. R ⁵ II: H, OH, halogen, C ₁ -C ₄ alkyl.

Preferred ranges of X are the following groups.
That is, XI: one to three substituents arbitrarily selected from halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and phenyl. XII: halogen, C ₁ ~C ₄
One or two substituents arbitrarily selected from alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy and phenyl.

Preferred ranges of Ra are the following groups.
That, RaI: C ₁ ~C ₄ alkyl.

Preferred ranges of Rb are the following groups.
That, RbI: C ₁ ~C ₆ alkyl, optionally substituted by T ¹ phenyl.

The preferred range of Rc is the following group.
That is, RcI: phenyl which may be substituted with halogen, C ₁ -C ₄ alkyl, or C ₁ -C ₄ alkoxy.

Preferred ranges of Rd are the following groups. That, RDI: halogen, optionally substituted by C ₁ -C ₄ alkyl benzoyl.

The preferred range of Re is the following group.
That, ReI: C ₁ ~C ₄ alkyl, optionally substituted by T ¹ phenyl.

Preferred ranges of Rf are the following groups.
That is, RfI: C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₁ -C _6
6 haloalkyl, C ₂ -C ₄ alkoxyalkyl, C ₁ -C optionally substituted with ₃ alkyl C ₃ -C ₆ cycloalkyl,
C ₁ -C ₆ alkoxy, C ₃ -C ₆ cycloalkoxy, phenyl optionally substituted with T ³ . RfII: C ₁ ~C ₆ alkyl, C ₁
-C ₃ optionally substituted by alkyl C ₃ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, phenyl optionally substituted with T ^3.

The preferred range of Rg is the following group.
_{That, RgI: OH, C 1 ~C} 6 alkoxy or C ₁ -C ₄ alkylsulfenyl.

The preferred ranges of Rh are the following groups.
That, RhI: C ₁ ~C ₆ alkoxy, C ₁ -C ₄ alkylsulfenyl.

The preferred ranges of Ri are the following groups.
That is, RiI: H, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or Ri and Rj represent an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which each is bonded. A 5- or 6-membered ring group which may be contained may be formed.

Preferred ranges of Rj are the following groups.
That is, RjI is H, C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl or benzyl, or Ri and Rj are each an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which they are bonded. A 5- or 6-membered ring group which may be contained may be formed.

Preferred ranges of Rk are the following groups.
_{That, RkI: H, C 1 ~C} 6 alkyl.

Preferred ranges of U ¹ are the following groups.
^{That, U 1 I: H, C} 1 ~C 6 alkyl, COORa, phenyl or benzyl.

Preferred ranges of U ² are the following groups.
^{That, U 2 I: H, C} 1 ~C 6 alkyl, COORa, phenyl or benzyl.

[0041] Preferred T ¹ range is the following group.
That is, T ¹ I: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl.

The preferred T ³ range is the following group.
That is, T ³ I: halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁
-C ₄ alkylsulfenyl, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, 1 to 3 substituents selected arbitrarily from among -NU ¹ U ^2. T ³ II: halogen,
C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, one to three substituents selected arbitrarily from among the C ₁ -C ₄ alkoxy.

Each group within the above-mentioned preferred substituents can be arbitrarily combined.

Next, A, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Ra, Rb,
Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, T 1, T 2, T 3, U 1
And shows an example of the atoms and groups in the definition of U ^2.

The halogen atom in the definition of R ⁴ , R ⁵ , X, Rc, Rd, T ¹ , T ² and T ³ includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom , A chlorine atom and a bromine atom.

A, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Ra, Rb, Rc,
Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, T 1, T 3, the alkyl in the definition of U ¹ and U ^2, linear or branched methyl as alkyl, ethyl, n- propyl, Isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, pentyl-1, pentyl-2, pentyl-3, 2-methylbutyl-1, 2-methylbutyl-2, 2-methylbutyl-3, 3-methylbutyl- 1,2,2-dimethylpropyl-1, hexyl-1, hexyl-2, hexyl-3, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,
2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-
Ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl and the like can be mentioned, and each is selected within the range of the specified number of carbon atoms.

A, R ¹ , R ³ , R ⁴ , R ⁵ , X, Rc, Rd, Re, Rf,
As the haloalkyl in the definition of T ¹ and T ³ , fluoromethyl, chloromethyl, bromomethyl, fluoroethyl, chloroethyl, bromoethyl, fluoro-n-propyl, chloro-n-propyl, difluoromethyl, Chlorodifluoromethyl,
Trifluoromethyl, dichloromethyl, trichloromethyl, difluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluorochloroethyl, hexafluoro-n
-Propyl, chlorobutyl, fluorobutyl and the like, and each is selected from the specified carbon number range.

Cycloalkyl in the definition of A, R ¹ , Rf, Ri, Rj and Rk includes cyclopropyl, 1-methylcyclopropyl, 2,2,3,3-tetramethylcyclopropyl,
Cyclobutyl, 1-ethylcyclobutyl, 1-n-butylcyclobutyl, cyclopentyl, 1-methylcyclopentyl,
Cyclohexyl, 1-methylcyclohexyl, 4-methylcyclohexyl, cycloheptyl and the like can be mentioned.

The C ₁ -C ₄ alkyl substituted with Rc in the definition of Rf includes benzyl, 2-chlorobenzyl, 3-bromobenzyl, 4-chlorobenzyl, 4-methylbenzyl,
tert-butylbenzyl, 2-methylbenzyl, 2-methoxybenzyl, 1-phenylethyl, 1- (3-chlorophenyl) ethyl, 2-phenylethyl, 1-methyl-1-phenylethyl, 1- (4-chlorophenyl) 1-methylethyl, 1- (3-chlorophenyl) -1-methylethyl, 1-phenylpropyl, 2-
Phenylpropyl, 3-phenylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-methyl-1-phenylpropyl, 1-methyl-2-
Phenylpropyl, 1-methyl-3-phenylpropyl, 2-
Methyl-2-phenylpropyl, 2- (4-chlorophenyl) -2-
Methyl-propyl and 2-methyl-2- (3-methylphenyl)-
Propyl and the like.

The phenyl which may be substituted by T ¹ in the definition of Rb and Re includes phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl ,
2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 4-iodophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-fluoro-4 -Chlorophenyl, 2,3,4,5,6
-Pentafluorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,5-dimethylphenyl, 4-methyl-2,3,5,6-tetrafluorophenyl, 2-methoxyphenyl, 3-methoxyphenyl Methoxyphenyl, 4-methoxyphenyl, 2,6-methoxyphenyl, 3,4-dimethoxyphenyl and 3,4,5-trimethoxyphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoro Methylphenyl and the like can be mentioned.

R ⁴ , R ⁵ , X, Rc, Rd, Rf, Rg, Rh, T ¹ and T
^As the alkoxy in the definition of ³ , methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, se
c-butoxy, tert-butoxy, n-pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy, 3-methylbutyloxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl Propoxy, 1-ethylpropyloxy, n-hexyloxy, 1-methylpentyloxy,
2-methylpentyloxy, 3-methylpentyloxy, 4-
Methylpentyloxy, 1,1-dimethylbutyloxy, 1,
2-dimethylbutyloxy, 1,3-dimethylbutyloxy,
2,2-dimethylbutyloxy group, 2,3-dimethylbutyloxy group, 3,3-dimethylbutyloxy, 1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy, 2,2-trimethylpropyloxy, 1-ethyl-1
-Methylpropyloxy, 1-ethyl-2-methylpropyloxy and the like, and each is selected from the specified carbon number range.

-NU ¹ U ² in the definition of Rf and T ³ includes methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino,
sec-butylamino, tert-butylamino, n-pentylamino, 1-methylbutylamino, 2-methylbutylamino,
3-methylbutylamino, 1,1-dimethylpropylamino,
1,2-dimethylpropylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1-
Methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-
Dimethylbutylamino, 2,2-dimethylbutylamino, 2,
3-dimethylbutylamino, 3,3-dimethylbutylamino,
1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-
Trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino, dimethylamino, diethylamino, di-n-propylamino, diisopropylamino, di-n-butylamino, di-sec- Butylamino, diisobutylamino, di-n-pentylamino,
Di-n-hexylamino, methylethylamino, methylpropylamino, methylisopropylamino, methylbutylamino, methyl-sec-butylamino, methylisobutylamino, methyl-tert-butylamino, methylpentylamino, methylhexylamino, ethyl Propylamino, ethylisopropylamino, ethylbutylamino,
Ethyl-sec-butylamino, ethylisobutylamino,
Ethylpentylamino, ethylhexylamino, phenylamino, benzylamino, N-methylacetamide, N-
Ethyl acetamide and N-phenylacetamide N-acetylacetamide and the like can be mentioned, and each is selected within the range of the specified number of carbon atoms.

Examples of haloalkoxy in the definition of R ⁴ , R ⁵ , X, Rc, Rd, Rf and T ³ include straight-chain or branched-chain haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoro Methoxy, chlorodifluoromethoxy, bromodifluoromethoxy, dichlorofluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, bromomethoxy, fluoroethoxy, chloroethoxy, bromoethoxy, difluoroethoxy, trifluoroethoxy, tetrafluoroethoxy, pentafluoroethoxy, Trichloroethoxy, trifluorochloroethoxy, fluoropropoxy, chloropropoxy, bromopropoxy, fluorobutoxy,
Chlorobutoxy, fluoro-iso-propoxy and chloro-
iso-propoxy and the like.

The alkylsulfenyl in the definition of R ¹ , R ⁴ , R ⁵ , X, Rg, Rh and T ³ includes methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec -Butylthio and tert-butylthio.

The alkylsulfinyl in the definition of R ¹ , R ⁴ , R ⁵ , X and T ³ includes methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, iso-butylsulfinyl, sec-butylsulfinyl and tert-butylsulfinyl and the like.

The alkylsulfonyl in the definition of R ¹ , R ⁴ , R ⁵ , X and T ³ includes methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, iso-propylsulfonyl, n-butylsulfonyl, iso-butylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl and the like.

The alkoxyalkyl in the definition of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , X, Rc, Rd and Rf includes methoxymethylmethyl, ethoxymethyl, n-propoxymethyl, is-propoxymethyl
o-propoxymethyl, n-butoxymethyl, iso-butoxymethyl, sec-butoxymethyl, tert-butoxymethyl, n
-Pentyloxymethyl, methoxyethyl, ethoxymethyl, methoxypropyl and the like, each being selected from the specified carbon number range.

In the definition of A and Rf, naphthyl is 1
-Naphthyl and 2-naphthyl.

[0059] R The pyridinyl substituted by T ¹ in the ^second definition, may be substituted by T ¹ 2-pyridyl, with or 3-pyridyl and T ¹ which may be substituted by T ¹ substituted or 4-pyridyl can be mentioned also, preferably which may be optionally 2-pyridyl substituted with are optionally may pyridyl and T ¹ is also substituted by T ^1, more preferably substituted by T ¹ 3-pyridyl which may have been used.

As the haloalkylsulfenyl in the definition of R ⁴ , R ⁵ , X and T ³ , a straight-chain or branched-chain haloalkylthio is fluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, trifluoromethylthio, trichloromethylthio. , 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, fluoroethylthio, pentafluoroethylthio, and fluoro-iso-propylthio groups.

As the haloalkylsulfinyl in the definition of R ⁴ , R ⁵ , X and T ³ , a straight-chain or branched-chain haloalkylsulfinyl is fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl, trifluoromethylsulfinyl , Trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 1,1,2,2-tetrafluoroethylsulfinyl, fluoroethylsulfinyl, pentafluoroethylsulfinyl, fluoro-iso-propylsulfinyl and the like.

As the haloalkylsulfonyl in the definition of R ⁴ , R ⁵ , X and T ³ , linear or branched haloalkylsulfonyl is fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, trifluoromethylsulfonyl , Trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, fluoroethylsulfonyl, pentafluoroethylsulfonyl and fluoro-iso-propylsulfonyl.

Alkenyloxy in the definition of Rf, Ri, Rj and Rk includes allyloxy, 2-propenyloxy, 2-butenyloxy and 2-methyl-2-propenyl as C ₂ -C ₄ linear or branched alkenyloxy. Oxy and the like.

Alkenyl in the definition of A, R ¹ , X, R ³ , R ⁴ , R ⁵ , Ri, Rj and Rk includes allyl, 2-propenyl, 2-butenyl, 2-methyl-2-propenyl, -Methyl-3-
Pentenyl, 2-hexenyl and the like can be mentioned, each of which is selected by the designated number of carbon atoms.

The alkali metal in the definition of R ² includes lithium, sodium and potassium.

The alkaline earth metal in the definition of R ² includes magnesium, calcium, strontium or barium, preferably magnesium, calcium or barium.

The ammonium group represented by NHRiRjRk in the definition of R ² includes ammonium, monomethylammonium, dimethylammonium, trimethylammonium, diethylammonium, triethylammonium, diisopropylammonium, diisopropylethylammonium, hexyl A methylammonium group, a cyclopropylmethylammonium group, a cyclohexylmethylammonium group, an allylmethylammonium group, a benzylmethylammonium group or a 4-methylcyclohexylethylammonium group, or two of Ri, Rj and Rk are each A heterocyclic 5-, 6-, 7- or 8-membered ammonium group which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which it is bonded Is raised.

Ri, Rj and Rk in the definition of Ri, Rj and Rk
Heterocyclic 5- to 8-membered ammonium groups which may contain an oxygen atom, a nitrogen atom or a sulfur atom together with the nitrogen atom to which two of them are bonded, include pyrrolidine, pyrazolidine, imidazolidine, Oxazolidine, isoxazolidine, thiazolidine, piperidine, piperazine, morpholine, thiamorpholine, hexamethyleneimine, heptamethyleneimine.

[0069] U ¹ and U ¹ in the definition of U ² and U ² and the oxygen atom with the nitrogen atom to which they are attached as a 8-membered ring to 5 no good heterocyclic also contain a nitrogen atom or a sulfur atom , Pyrrolidine, pyrazolidine, imidazolidine,
Oxazolidine, isoxazolidine, thiazolidine,
Examples thereof include piperidine, piperazine, morpholine, thiamorpholine, hexamethyleneimine, and heptamethyleneimine.

C ₃ -C ₆ halocycloalkyl in the definition of Rf includes fluorocyclopropyl, difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl, 1-methyl-2,2-dichlorocyclopropyl, chlorocyclobutyl, Examples include dichlorocyclobutyl, chlorocyclopentyl, dichlorocyclopentyl, chlorocyclohexyl, dichlorocyclohexyl, tetrafluorocyclobutyl and the like.

The cyclopropyl substituted with T ² and C ₁ -C ₄ alkyl in the definition of Rf includes 2,2-dimethyl-3-
(2,2-dimethylethenyl) -cyclopropyl, 3- (2,2-dibromoethenyl) -2,2-dimethylcyclopropyl, 3- (2,2-
Dichloroethenyl) -2,2-dimethylcyclopropyl, 3-
(2,2-chlorotrifluoroethenyl) -2,2-dimethylcyclopropyl and the like.

The C ₃ -C ₆ cycloalkoxy group which may be substituted with C ₁ -C ₄ alkyl in the definition of Rf includes cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy, 1-cyclohexyloxy, And a methylcyclopropoxy group.

In the definition of Rf, R _{3 and} C ₃ -C ₄ cycloalkyl substituted by a halogen atom include 2,2-dichloro
-1-phenylcyclopropyl, 2,2-dichloro-1- (3-chlorophenyl) -cyclopropyl, 2,2-dichloro-1- (4-methoxyphenyl) -cyclopropyl, 2,2-dichloro-1- (4-ethoxyphenyl) -cyclopropyl, 2,2-dichloro-1- (4-
iso-propyloxyphenyl) -cyclopropyl, 2,2-dichloro-1- (4-t-butylphenyl) -cyclopropyl,
2,2-Dichloro-1- (4-methoxyphenyl) -3-phenylcyclopropyl, 1- (4-ethoxyphenyl) -2,2,3,3-tetrafluorobutyl and the like can be mentioned.

Examples of the cyclopropyl group substituted with Rc and an alkyl group having 1 to 4 carbon atoms in the definition of Rf include 2,2-dimethyl-1-phenylcyclopropyl group, 1- (4-chlorophenyl) -2, 2-dimethylcyclopropyl group, 2,2-dimethyl-3
-Phenylcyclopropyl group, 3- (3-chlorophenyl) -2,
2-dimethylcyclopropyl group, (4-chlorophenyl) -2,2
-Dimethyl-3-phenylcyclopropyl group, (4-bromophenyl) -2,2-dimethyl-3-phenylcyclopropyl group,
Examples thereof include a 2,2-dimethyl-3- (4-methylphenyl) -cyclopropyl group and a (4-tert-butylphenyl) -2,2-dimethyl-3-phenylcyclopropyl group.

The C ₃ -C ₆ cycloalkyl substituted by Rc in the definition of Rf includes 1-phenylcyclopropyl, 1-phenyl
(3-chlorophenyl) -cyclopropyl, 1- (4-chlorophenyl) -cyclopropyl, 1- (4-bromophenyl) -cyclopropyl, 1- (4-fluorophenyl) -cyclopropyl, 1
-(4-ethylphenyl) -cyclopropyl, 1- (4-propylphenyl) -cyclopropyl, 2-phenylcyclopropyl, 1-phenylcyclobutyl, 2-phenylcyclobutyl, 1-phenylcyclopentyl, 1- (4 -Chlorophenyl)
-Cyclopentyl, 2-phenylcyclopentyl, 3-phenylcyclopentyl, 1-phenylcyclohexyl, 1- (3
-Fluorophenyl) -cyclohexyl, 1- (4-chlorophenyl) -cyclohexyl 1- (4-tert-butylphenyl) -cyclohexyl, 2-phenylcyclohexyl, 3-phenylcyclohexyl, 4-phenylcyclohexyl and the like.

The compound of the present invention is useful for so-called agricultural pests that infest agricultural and horticultural crops and trees, so-called livestock pests that infest livestock and poultry, so-called sanitary pests that have various adverse effects on human living environments such as houses, and warehouses. So-called stored pests that injure stored grains and the like, and any pests such as mites, nematodes, molluscs, and crustaceans that occur and injure in similar situations can be effectively controlled at low concentrations.

Insects which can be controlled using the compound of the present invention;
Specific examples of mites, nematodes, molluscs, and crustaceans include, but are not limited to, the following.

Nikameiga, Kobunomeiga, Futaobikoyaga, Ichimonjiseri, Konaga, Yotoga, Monshiro butterfly, Kaburayaga, Hasmonyoto, Shiroichimonjito, Chinokokakumonhamaki, Chahamaki, Momomosinui, Nishihimemeshinkui, Apple tortoise , European corn borer, fall army worm, codling moth, and Lepidopteran pests such as white-winged starling, black leafhopper, brown planthopper, peach peach aphid, cotton aphid, onsic whitefly, tobacco whitefly, pear white lice, tsutsujimushibayashi, swordfish, and more Hemiptera pests such as the stink bug, the stink bug and the bedbug, niju Yahoshitentou, cupreous chafer, rice water weevil, sweet potato weevil, cucurbit leaf beetle, Kisujinomihamushi, Colorado potato beetle, Gomadarakamikiri, Monochamus alternatus, corn rootworm, Kokokuzou, grana Lee weevil and coleopteran pests such as red flour beetle,

Diptera and mosquitoes of the mosquitoes, such as the mosquitoes, the mosquitoes, the mosquitoes, the mosquitoes, and the mosquitoes such as the mosquitoes, the mosquitoes and the mosquitoes, Eye pests,
Thrips pests such as Thrips palmi, Thrips palmi, Citrus thrips, Thrips palmi and Thrips palmi, Thrips pests such as black cockroaches, Yamato cockroaches and German cockroaches; , Termite pests such as house termites, yamato termites and taiwan termites, isoptera pests such as cat fleas, human fleas and keops muskleaf, hazel lice pests such as chick and white lice, and lice and lice lice such as lice and lice Eye pests, mandarin spider mites, apple spider mites, spider mites, spider mites such as spider mites,

[0099] Fucus mites, such as Citrus mite, Poisonous mite, Tulip rust mite, and Rhipicephalus sanguineus, Dermatophagoid mites, such as Dermatophagoids and Cyclamen mites, Dermatophagoides, such as Dermatophagoides farinae and Robin's mite, Dermatophagoides farinae, such as honey bee mites Nematodes such as narcissus mite, sarcophagidae such as sarcoptic mite, sweet potato nematode, kitaneko nematode, kitanegususarenetto, walnut nematode, nematodes such as potato cyst nematode and pine wood nematode; And molluscs, crustaceans such as locust beetles, and the like.

That is, the compounds of the present invention can effectively control pests and plant diseases of the order Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites and Mite and Lice at low concentrations. it can. On the other hand, the compounds of the present invention include extremely useful compounds having almost no adverse effects on mammals, fish, crustaceans and beneficial insects.

The compound (1) of the present invention can be synthesized by the method described in Scheme 1. That is, the present compound (1)
Can synthesize a part of the compound of the present invention by reacting a cyanomethyltriazole derivative represented by the general formula (2) with a carboxylic acid derivative represented by the general formula (3) in the presence of a base. And further reacting this with the compound represented by the general formula (4) to obtain the compound of the present invention. Specific examples of the compound represented by the general formula (4) include acyl halides, benzoyl halides, alkyl halides, benzyl halides, alkoxyalkyl halides, alkoxyalkoxyalkyl halides, phenoxyalkyl halides, and benzyloxy. Alkyl halides, alkyl sulfonates, benzene sulfonates, toluene sulfonates,
α-haloketones and α-haloesters. [Scheme 1]

[0083]

Embedded image

[A, R ¹ , R ² , R ³ , R ⁴ and R in Scheme 1
⁵ represents the same meaning as described above, L ¹ and L ² are good leaving groups,
For example, chlorine atom, bromine atom, iodine atom, C ₁ -C ₄ alkylsulfonyloxy, benzene sulfonyloxy,
Toluenesulfonyloxy, 1-imidazolyl and 1
-Pyrazolyl and the like. ].

In some cases, it is preferable to use a base in the methods described above. Examples of the base used include alkali metal alkoxides such as sodium ethoxide, sodium methoxide and potassium tert-butoxide, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. And organic bases such as triethylamine, pyridine and DBU, organic lithium compounds such as butyllithium, lithium amides such as lithium diisopropylamide and lithium bistrimethylsilylamide, and sodium hydride.

The above-mentioned reaction can be carried out in a solvent inert to the reaction. Examples of the solvent include lower alcohols such as methanol and ethanol, aromatic hydrocarbons such as benzene and toluene, diethyl ether and tetrahydrofuran. , 1,4-dioxane, 1,2-dimethoxyethane and 1,
Ethers such as 2-diethoxyethane, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, halogenated hydrocarbons such as methylene chloride, chloroform and 1,2-dichloroethane, dimethylformamide,
Examples thereof include amides such as dimethylacetamide and 1,3-dimethylimidazolidinone, nitriles such as acetonitrile, dimethylsulfoxide, and a mixed solvent thereof. In some cases, a mixed solvent of these solvents and water can also be used, and good results may be obtained by adding a quaternary ammonium salt such as tetra-n-butylammonium bromide as a catalyst. Reaction temperature is -70 ° C
Can be set to any temperature from 200 ° C to
0 ° C to 150 ° C or -70 ° C when using a solvent
To the boiling point of the solvent. The base ranges from 0.05 to 10 equivalents, preferably 0.05 to 3 equivalents, of the reaction substrate.

The compound of the present invention can be obtained from the reaction solution by a conventional method. However, if it becomes necessary to purify the compound of the present invention, it can be separated and purified by any purification method such as recrystallization, column chromatography and the like. Can be.

In the compounds included in the present invention, compounds having an asymmetric carbon include optically active compounds (+) and (-).

Examples of the compounds included in the present invention are shown in Table 1. The abbreviations in the table have the following meanings.

Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pen: pentyl group, Hex: hexyl group, Hep: heptyl group, Oct: octyl group, Non: nonyl group, Dec: Decyl group, Ph: phenyl group, n: normal,
i: iso, s: secondary, t: tertiary, c: cyclo.

[Table 1]

[0092]

Embedded image

[0093]

[Table 1]

[0094]

[Table 2]

[0095]

[Table 3]

[0096]

[Table 4]

When the compound of the present invention is applied as a pesticidal agent, it is usually mixed with a suitable solid carrier or liquid carrier, and if necessary, a surfactant, a penetrant, a spreading agent, a thickener, a deicing agent, Binders, anti-caking agents, disintegrants and decomposition inhibitors are added, and liquids, emulsions, wettable powders, aqueous solvents,
It can be practically used in any form of formulation such as water dispersible granules, aqueous solvents for granules, suspensions, emulsions, suspoemulsions, microemulsions, powders, granules and gels. Further, from the viewpoint of labor saving and improvement of safety, the above-mentioned preparation of any dosage form can be provided by being enclosed in a water-soluble package.

Examples of the solid carrier include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite and diatomaceous earth, calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride. And the like, synthetic silicic acid and synthetic silicate.

Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone;
Esters such as γ-butyrolactone; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil; and water.

These solid and liquid carriers may be used alone or in combination of two or more.

Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, and polyoxyethylene polyoxypropylene block copolymer. Nonionic surfactants such as oxyethylene sorbitan fatty acid esters, alkyl sulfates, alkyl benzene sulfonates,
Lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonic acid, salt of alkyl naphthalene sulfonic acid formalin condensate,
Anionic surfactants such as polyoxyethylene alkyl aryl ether sulfates and phosphates, polyoxyethylene styryl phenyl ether sulfates and phosphates, polycarboxylates and polystyrene sulfonates, alkylamine salts and alkyl quaternary ammonium salts; Examples include cationic surfactants and amphoteric surfactants such as amino acid type and betaine type.

The content of these surfactants is not particularly limited, but is preferably in the range of usually 0.05 to 20 parts by weight per 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.

When the compound of the present invention is used as a pesticide, other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators may be used as needed when formulating or spraying. It may be applied in combination with an agent, a synergist, a fertilizer, a soil conditioner and the like.

In particular, by applying a mixture with other pesticides or plant hormones, it is possible to expect a reduction in cost due to a decrease in the amount of applied medicine, an increase in the insecticidal spectrum due to the synergistic action of the mixture, and a higher pest control effect. On this occasion,
A combination with a plurality of known pesticides is also possible at the same time. Examples of the kind of pesticide to be used in combination with the compound of the present invention include, for example, Farm Chemicals Handbook (Farm
Chemicals Handbook), 1994, and the like. Specific examples of the common names are as follows, but are not necessarily limited thereto.

Fungicide: acibenzola
r), ampropylfos, anilazine (a
nilazine), azaconazole, azoxystrobin, benalaxil
xyl), benodanil, benomyl
l), benzamacril, binapacacryl (binapacryl), biphenyl (biphenyl), bitertanol (bitertanol), bethoxazine (bethoxazine),
Bordeaux mixture, blasticidin-
S (blasticidin-S), bromoconazol
e), bupirimate, butiobate (but
hiobate), calcium polysulfide (calcium polys)
ulfide), captafol, captan, copper oxychlo
ride), carpropamid, carbendazim, carbendin, carboxin, quinomethionate, clobenthiazon (chlobenthiazone), chlorfenazole
zol), chloroneb, chlorothalonil (ch
lorothalonil), chlozolinate, kufraneb,

Cymoxanil, cyproconazol, cyprodinil (cyprodini)
l), cyprofuram (cyprofuram), debacarb (debac
arb), dichlorophen, diclobutrazol, diclofuranide (diclhlo)
fluanid), diclomedine, dichloran, dietofencar
b), diclosymet, difenoconazole, diflumetorin
im), dimethirimol,

Dimethomorph, diniconazole, diniconazole-M (dinicon
azole-M), dinocap, diphenylamine, dipyrithione,
Ditalimphos (ditalimfos), dithianon (dithiano)
n), dodemorph, dodine, dorazoxolon, edefenophos (edifen)
phos), epoxyconazole (epoxiconazole), etaconazole (etaconazole), etirimol (ethirimo)
l), etridiazole, famoxadone, fenarimol, febuconazole, fenfuram
am),

Fenpiclonil, fenpropidin, fenpropimorph (f
enpropimorph), fentin, ferbam, ferimzone, fluazinam, fluazioxonil,
Fluorimide, fluquinconazole, flusilazol
e), Flusulfamide, Flutolanil, Flutriafol (flutriafo)
l), folpet, fosetyl-aluminum, fuberidazole
azole), furalaxyl, fenamidone, fenhexamid,

Guazatine, hexachlorobenzene, hexaconazole (h
exaconazole), hymexazol, imazalil, imibenconazole
le), iminoctadine, ipconazole, iprobenfos, iprodione, isoprothiolane (isoprot)
hiolane), iprovalicarb,

Kasugamycin, kresoxim-methyl, mankappa (m
ancopper), mancozeb (mancozeb), manneb (mane
b), mepanipyrim, mepronil (mepr
onil), metalaxyl, metconazole, metiram, metinominostrobin, microbutanyl (myclobu)
tanil), nabam, nickel bis (dimethyldithiocarba)
mate)), nitrothal-iso
propyl), nuarimol, octilinone (oc)
thilinone), ofurace, oxadixyl, oxycarboxin,
Oxpoconazole fumarat
e),

[0111] Pefurzoate, penconazole, pencuron (pencycuro)
n), phthalide, piperaline (piperali)
n), polyoxins (polyoxins), probenazole (pr
obenazole), prochloraz, procymidone, propamocarb hydrochloride
carb hydrochloride), propiconaz
ole), propineb, pyrazophos (pyrazop)
hos), pyrifenox, pyrimethanil, pyroquilon, quinoxyfen, quintozen
e),

Sulfur, spiroxamine (spirox)
amine), tebuconazole, tecnazene, tetraconazol
e), thiabendazole, thifluzamide, thiophanate-methyl (thioph
anate-methyl), thiram, tolclofos-methyl, tolylfluanide (tolylflu
anid), triadimefon, triadimenol, triazoxide
e), tricyclazole, tridemorph, triflumizol
e), triforine, triticonazole (tr
iticonazole, validamycin, vinclozolin, zineb and ziram.

Bactericide: Streptomycin (st
reptomycin, oxyterracycline
ine) and oxolinic acid.

Nematicides: aldoxycarb
b), fosthiazate, fosthietan, oxamyl, fenamiphos and the like.

Acaricides: amitraz, bromopropylate, chinomethionat, chlorobenzilate
late), clofentezine, cyhexatine, dicofol, dienochlor, etoxaz
ole), fenazaquin, fenbutatin oxide, fenpropathrin, fenproxim
ate), halfenprox, hexythiazox, milbemectin (milbe)
mectin), propargite, pyridaben, pyrimidifen and tebufenpyrad.

Insecticides: abamectin, acephate, acetamipir
id), azinphos-methyl, bendiocarb, benfurac
arb), bensultap, bifenthrin, buprofezin, butocarboxin, carbary
l), Carbofuran, Carbosulfan, Cartap, Cartap, Chlorfenapyr, Chlorpyrif
os), chlorfenvinphos (chlorfenvinphos), chlorfluazuron (chlorfluazuron), clothianidin (clothianidin), chromafenozide (chromafenozid)
e), chlorpyrifos-methyl,
Cyfluthrin, beta-cyfluthrin, cypermethrin
n), cyromazine,

Cyhalothrin, lambda
Cyhalothrin (lambda-cyhalothrin), deltamethrin (deltamethrin), diafenthiuron (diafenthiuro)
n), diazinon, diacloden (diacl)
oden), diflubenzuron, dimethylvinphos, diphenolane (dio)
fenolan), disulfoton, dimethoate, EPN, esfenvalerate (esf)
envalerate), ethiofencarb,
Ethiprole, etofenprox (e
tofenprox), etrimfos, fenitrothion, fenobucar
b), fenoxycarb, fenpropathrin, fenvalerate
rate), fipronil, flucythrinate, flufenoxulone
ron), flufenprox, tau-
Tau-fluvalinate, honophos (fonop)
hos), formetanate, formothion, furathiocar
b),

Halofenozide, hexaflumuron, hydramethylnon (hydr)
amethylnon), imidacloprid, isofenphos, indoxacarb (indo
xacarb), isoprocarb, isoxathion, lufenuron,
Malathion, metaldehyd
e), methamidophos, methidathion, methacrifos, metalcarb, metalcarb, methomyl, methoprene, methoxychlor
hlor), methoxyfenozide, monocrotophos, muscaule
lure), nitenpyram, omethoate, oxydemeton-methyl
methyl), oxamyl,

Parathion, parathion-
Methyl (parathion-methyl), permethrin (permethr)
in), phenthoate, phoxime (ph
oxim), phorate, phosalon
e), phosmet, phosphamidon (phosph
amidon), pirimicarb, pirimiphos-
Methyl (pirimiphos-methyl), profenophos (profe
nofos), pymetrozine, pyraclofos, pyriproxyfe
n), rotenone, sulprofo
s), silafluofen, spinosad, sulfotep, tebfenozide, teflubenzur
on), tefluthrin, terbufos (terb)
ufos), tetrachlorovinphos
s), thiodicarb, thiomethoxam (t
hiamethoxam), thiofanox, thiometon, tolfenpyra
d), tralomethrin, trichlorfon, triazuron, triflumuron, and vamidot
hion).

The applied amount of the compound of the present invention varies depending on the application scene, application time, application method, cultivated crops and the like, but is generally 0.000 per hectare (ha) as an active ingredient.
About 5 to 50 kg is appropriate.

Next, specific examples of the formulation of the preparation when the compound of the present invention is used will be shown. However, the composition examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight.

[Wettable powder] Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others, for example, anti-caking agent, anti-decomposition agent, etc. I can give you.

[Emulsion] Compound of the present invention 0.1 to 30 parts Liquid carrier 45 to 95 parts Surfactant 4.9 to 15 parts Others 0 to 10 parts Others include, for example, spreading agents and decomposition inhibitors. Can be

[Suspension] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, an antifreezing agent and a thickener. And the like.

[Water-Dispersible Granule] Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, a binder and a decomposition inhibitor. No.

[Solution] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Others include, for example, an antifreezing agent and a spreading agent.

[Granules] Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, a binder and a decomposition inhibitor.

[Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0 to 5 parts Others include, for example, a drift inhibitor and a decomposition inhibitor.

[Preparation Examples] Next, specific preparation examples of the pesticidal composition containing the compound of the present invention as an active ingredient are shown, but the present invention is not limited thereto.

[0130] In the following formulation examples, "parts" means parts by weight.

[Formulation Example 1] Water-dispersible compound of the present compound No. 1 2 20 parts Pyrophyllite 76 parts Solpol 5039 2 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) Carplex # 80D 2 parts (synthetic hydrous silicic acid: Shiono The above is uniformly mixed and pulverized into a wettable powder.

[Formulation Example 2] Emulsion Compound of the present compound no. 25 parts Xylene 75 parts N-methylpyrrolidone 15 parts Solpol 2680 5 parts (mixture of nonionic surfactant and anionic surfactant: trade name of Toho Chemical Industry Co., Ltd.) And

[Formulation Example 3] Suspending agent (flowable agent) 2 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corp. trade name) Lunox 1000C 0.5 parts (Anionic surfactant: Toho Chemical Industry Corp. trade name) Xanthan gum 0.2 Part Water 64.3 parts After uniformly mixing the above, wet pulverization is performed to obtain a suspending agent.

[Compounding Example 4] Water dispersible granule (dry flowable) 2 75 parts Hytenol NE-15 5 parts (anionic surfactant: Daiichi Kogyo Seiyaku Co., Ltd.) Vanirex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd.) Carplex # 80D 10 parts (synthetic hydrous silicic acid: trade name of Shionogi & Co., Ltd.) After uniformly mixing and pulverizing the above, adding a small amount of water, stirring and mixing, granulating with an extrusion granulator, drying and granulating water. It should be a sum.

[Formulation Example 5] Granules Compound of the present invention 25 parts Bentonite 50 parts Talc 45 parts After uniformly mixing and pulverizing the above, a small amount of water is added and mixed with stirring, granulated by an extrusion granulator, and dried to obtain granules.

[Formulation Example 6] Powder Compound No. 2 3 parts Carplex # 80D 0.5 part (Synthetic hydrated silicic acid: Shionogi & Co., Ltd. brand name) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above components are uniformly mixed and pulverized to form a powder.

When used, the above-mentioned wettable powder, emulsion, flowable powder and water-dispersible granule are diluted 50 to 20,000-fold with water to obtain an active ingredient of 0.005 to 0.005 per hectare (ha).
Spray to 50kg.

[0138]

EXAMPLES The synthesis examples, preparation examples, and test examples of the compound of the present invention are specifically described below as examples, but the present invention is not limited to these examples.

[Synthesis Example 1] 3- (1,4-dimethylpyrazole-
5-yl) -3-hydroxy-2- (1-methyl-3-phenyl-1,2,4-
Triazol-5-yl) -acrylonitrile (Compound N
o. Synthesis of 1) 0.5 g of 5-cyanomethyl-1-methyl-3-phenyl-1,2,4-triazole and 0.48 g of 1,4-dimethylpyrazole-5-carbonyl chloride were dissolved in 50 ml of tetrahydrofuran, and cooled on ice. Then 0.71 g of potassium tert-butoxide was added. After stirring at room temperature overnight, the solvent was distilled off under reduced pressure, and the resulting oil was dissolved in 50 ml of water, washed with toluene, the aqueous layer was acidified with concentrated hydrochloric acid, extracted with ethyl acetate, washed with water, and dried. Dried over sodium sulfate. The solid obtained by evaporating the solvent under reduced pressure was washed with isopropyl ether,
0.46 g of the title compound was obtained. Melting point: 188-191 ℃

[Synthesis Example 2] 3- (1,4-dimethylpyrazole-
5-yl)-(1-methyl-3-phenyl-1,2,4-triazole-5-
Yl) -3-pivaloyloxyacrylonitrile (compound N
o. Synthesis of 2) 3- (1,4-dimethylpyrazol-5-yl) -3-hydroxy-2-
Dissolve 0.3 g of (1-methyl-3-phenyl-1,2,4-triazol-5-yl) -acrylonitrile in 50 ml of chloroform,
0.09 g of triethylamine was added and the mixture was ice-cooled, and 0.11 g of pivaloyl chloride was added dropwise. Stirred overnight at room temperature. The reaction mixture was washed with water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting crude product was subjected to silica gel chromatography (chloroform / ethyl acetate = 3/1).
0.21 g (3/2 of E-form and Z-form)
Mixture). Melting point: 130-133 ° C

Table 2 shows the structures and melting points of the compounds of the present invention synthesized according to the above scheme or the above synthesis examples.
Those not particularly described are mixtures of E-form and Z-form. The abbreviations in the table have the same meaning as described above.

[Table 2]

[0143]

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[0144]

[Table 5]

[Test Examples] The usefulness of the compound of the present invention as a pesticide will be specifically described in the following test examples. The following compounds were used as control compounds.
A and compound B were used. Compound A is WO 98/42683 No. 2
The compound is Compound No. 2-1 in the table, and the compound B is a derivative of the compound No. 4-1 in Table 4 of WO / 42683.

[0146]

Embedded image

[Test Example 1] Insecticidal test against spider mite larvae A kidney bean was cut into a circular shape having a diameter of 3.0 cm using a leaf punch and placed on a wet filter paper on a styrene cup having a diameter of 7 cm. In addition to this, 10 spider mite larvae per leaf
The head was inoculated. A 5% emulsion of the compound of the present invention and the control compound A described in the specification (25% wettable powder was used depending on the compound) was diluted with water containing a spreading agent to adjust the concentration to 100 ppm. Was sprayed at a rate of 2 ml per styrene cup using a rotary spray tower, housed in a thermostatic chamber at 25 ° C., and the mortality after 96 hours was obtained from the following formula. Note that the test was performed in a two-section system.

[0148]

[Formula 1] Mortality rate = {number of dead insects / (number of dead insects + number of surviving insects)} x 100

As a result, the following compounds showed a mortality of 80% or more. Compound No. : 2,4,5,6,9,10,13,1
4. On the other hand, compound A used as a control did not show any effect at a concentration of 100 ppm.

[Test Example 2] Insecticidal test on adult female spider mite, Tetranychus urticae The kidney bean was cut into a circle having a diameter of 3.0 cm using a leaf punch and placed on a wet filter paper on a styrene cup having a diameter of 7 cm. In addition to this, adult female spider mite, 1 per leaf
0 animals were inoculated. Compound No. 14 of the present invention and 5 of control compound B
% Emulsion was diluted with water containing a spreading agent to adjust the concentration to 1.6 to 50 ppm, and this solution was sprayed using a rotary spray tower at a rate of 2 ml per styrene cup, and stored in a thermostat at 25 ° C.
The mortality after the lapse of time was determined from the formula of Test Example 1.
Note that the test was performed in a two-section system. The results are shown in Table 3.

[0151]

[Table 6]

[0152]

The compounds of the present invention exhibit excellent pest control activity.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Toshiro Miyake 1470 Shirooka, Shirooka-cho, Shiraoka-cho, Minami-Saitama-gun, Saitama Nissan Chemical Industry Co., Ltd. Inside the Biological Sciences Laboratory, Chemical Industries Co., Ltd. BB09 DA02 DA15 DA16 DD03

Claims (6)

[Claims] (1) Formula (1):[Where A is C₁~ C₆Alkyl, C_Two~ C₆Alkenyl, C₁~ C
₆Haloalkyl, C₁~ C_FourMay be substituted with alkyl
C_Three~ C₇Cycloalkyl, a group optionally substituted with X
Phenyl, naphthyl or pyridinyl; R¹Is H, C₁~ C₁₂Alkyl, C_Two~ C₁₂Alkenyl, C₁~ C₁₂
Haloalkyl, C₁~ C_FourOptionally substituted with alkyl
C_Three~ C₇Cycloalkyl, C_Two~ C₁₂Alkylsulfenyl
Alkyl, C_Two~ C₁₂Alkylsulfinylalkyl, C_Two
~ C₁₂Alkylsulfonylalkyl, C_Two~ C₁₂Alkoki
C substituted with a cycloalkyl or phenyl₁~ C _ThreeAlkyl, X
Optionally substituted phenyl, COORa, CONHRb, CON
RaRb, CORa or CO (N-piperidinyl); R^TwoIs H, C₁~ C_FourAlkyl, C_Two~ C_FourAlkoxyalkyl, C
H_TwoSCH_Three, CH_TwoOC_TwoH_FourOCH_Three, C substituted with Rc or Rd₁~
C_FourAlkyl, tetrahydropyranyl, trimethylsilyl
, SO_TwoRe, SO_TwoNHRb, SO_TwoNRaRb, C (S) NHRb, C (S) NRaR
b, CH_TwoCO_TwoRa, C (O) Rf, P (O) RgRh, P (S) RgRh, alkali
Metal, alkaline earth metal or NHRiRjRk; X is halogen, C₁~ C_FourAlkyl, C_Two~ C_FourAlkenyl, C₁
~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloal
Coxy, C₁~ C_FourAlkoxyalkyl, C₁~ C_FourAlkyls
Luphenyl, C₁~ C_FourAlkylsulfinyl, C₁~ C_FourAl
Killsulfonyl, C₁~ C_FourHaloalkylsulfenyl,
C₁~ C_FourHaloalkylsulfinyl, C₁~ C_FourHaloalkyl
Sulfonyl, NO_Two, CN, phenyl and phenoxy
1 to 3 substituents arbitrarily selected from among^FourAnd R^FiveAre independently H, OH, SH, NH_Two, Halogen, C₁
~ C_FourAlkyl, C_Two~ C_FourAlkenyl, C₁~ C_FourHaloalk
, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C₁~ C_Four
Alkoxyalkyl, C₁~ C_FourAlkylsulfenyl, C₁
~ C_FourAlkylsulfinyl, C₁~ C_FourAlkylsulfoni
, C₁~ C_FourHaloalkylsulfenyl, C₁~ C_FourHaloal
Killsulfinyl, C₁~ C_FourHaloalkylsulfonyl,
NO_TwoOr CN and R^ThreeIs C₁~ C_FourAlkyl, C_Two~ C_FourAlkenyl, C₁~ C_FourHaloa
Lucil or C₁~ C_FourIs an alkoxyalkyl, and Ra is C₁~ C₆Alkyl, Rb is H, C₁~ C₆Alkyl or T¹May be replaced by
Rc is halogen, C₁~ C_FourAlkyl, C_Two~ C_FourAlkenyl, C₁
~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloal
Coxy, C₁~ C_FourArbitrarily selected from among alkoxyalkyl
Rd is halogen, C₁~ C_FourAlkyl, C_Two~ C_FourAlkenyl, C₁
~ C_FourHaloalkyl, C₁~ C_FourAlkoxy, C₁~ C_FourHaloal
Coxy, C₁~ C_FourArbitrarily selected from among alkoxyalkyl
Is benzoyl optionally substituted by one or more of₁~ C_FourAlkyl, C_Two~ C_FourAlkenyl, C₁~ C_FourHaloa
Lucil or T¹Is a phenyl optionally substituted
Rf is C₁~ C₆Alkyl, C_Two~ C₆Alkenyl, C₁~ C₆Haloa
Lucil, C_Two~ C_FourAlkoxyalkyl, C_Three~ C₆Halocyclo
Alkyl, C substituted with Rc₁~ C_FourAlkyl, C₁~ C_FourAl
C which may be replaced by kill_Three~ C₇Cycloalkyl, Rc
And C₁~ C_FourCyclopropyl substituted with alkyl, Rc
And C substituted with halogen_Three~ C_FourCycloalkyl, T^TwoYou
And C₁~ C_FourCyclopropyl substituted with alkyl, with Rc
C replaced_Two~ C_FourAlkenyl, C₁~ C₆Alkoxy, C₁~
C_FourHaloalkoxy, C_Two~ C_FiveAlkenyloxy, C₁~ C_FourA
C optionally substituted with alkyl_Three~ C₆Cycloalkoxy
Si, benzyloxy, COORa, -NU¹U^Two, T^ThreeReplaced by
Phenyl, naphthyl, T¹May be replaced by
Pyridinyl or phenyl C₁~ C₆Rg and Rh are each independently OH, C₁~ C₆Alkyl, C₁~ C₆A
Lucoxy or C₁~ C_FourR, Rj and Rk are each independently H, phenyl, C₁~ C₆Al
Kill, C₁~ C_FourAlkenyl, C₁~ C_FourAlkenyloxy, C₁
~ C_ThreeC optionally substituted with alkyl_Three~ C₆Cycloal
Killed or benzyl or of Ri, Rj and Rk
Two of them, together with the nitrogen atom to which each is attached
May contain oxygen, nitrogen or sulfur atoms
May form a 5- to 8-membered ring group,¹Is halogen, C₁~ C_FourAlkyl, C₁~ C_FourHaloalkyl
Or C₁~ C_FourAlkoxy, T^TwoIs optionally substituted with halogen C_Two~ C_FourAlkene
And T^ThreeIs halogen, C₁~ C_FourAlkyl, C₁~ C_FourHaloalk
, C₁~ C_FourAlkoxy, C₁~ C_FourHaloalkoxy, C₁~ C_Four
Alkylsphenyl, C₁~ C_FourAlkylsphinyl, C₁~
C_FourAlkylsulfonyl, C₁~ C_FourHaloalkyl spheni
, C₁~ C_FourHaloalkylsphinyl, C₁~ C_FourHaloalk
Rusulfonyl, NO_Two, CN, CHO, -NU¹U^Two, Phenyl and
1 to 5 substitutions arbitrarily selected from phenoxy
Group, U¹And U^TwoIs independently H, C₁~ C₆Alkyl, COOR
represents a, phenyl or benzyl, or U¹And U^Two
Oxygen atom and nitrogen atom together with nitrogen atom
Or a 5- to 8-membered ring group optionally containing a sulfur atom
May be formed. Acrylonitrile compound represented by the formula
object. 2. A is phenyl, R ¹ is C ₁ -C ₆ alkyl, R ² is H or C (O) R f, R ³ is C ₁ -C ₆ alkyl, R ⁴ is H, halogen, C ₁ -C ₆ alkyl or C ₁ -C ₆ alkoxy, R ⁵ is H or C ₁ -C ₆ alkyl, Rf is according to claim 1, wherein the C ₁ -C ₆ alkyl Acrylonitrile compound. R ¹ is methyl or normal hexyl; R ³ is methyl; R ⁴ is H, chlorine atom, methyl or methoxy; R ⁵ is H, methyl or ethyl; 3. The acrylonitrile compound according to claim 2, which is butyl. 4. A is phenyl, R ¹ is C ₁ -C ₆ alkyl, R ² is H or C (O) R f, R ³ is C ₁ -C ₆ alkyl, R ^{4 is} is H, halogen or C ₁ -C ₆ alkyl, R ⁵ is H or C ₁ -C ₆ alkyl, Rf is C ₁ -C ₆ alkyl as claimed in claim 1 acrylonitrile compound according. 5. R ¹ is methyl or normal hexyl, R ³ is methyl, R ⁴ is H, chlorine atom or methyl, R ⁵ is H or methyl, R f is tertiary butyl The acrylonitrile compound according to claim 4. 6. An agricultural chemical comprising at least one acrylonitrile compound according to claim 1 as an active ingredient.