WO2006043654A1

WO2006043654A1 - Acetonitrile derivative, pest control agent, and method of using the same

Info

Publication number: WO2006043654A1
Application number: PCT/JP2005/019375
Authority: WO
Inventors: Nobuharu Andoh; Osamu Sanpei; Kazuyuki Sakata
Original assignee: Nihon Nohyaku Co., Ltd.
Priority date: 2004-10-22
Filing date: 2005-10-21
Publication date: 2006-04-27

Abstract

An acetonitrile derivative represented by the general formula (I): (I) (wherein A represents (VV) or (WW) B represents (XX) (YY) or (ZZ) and R represents hydrogen, C1-6 alkyl, etc. (Q1, Q2, Ar1, and Ar2 each represents phenyl, substituted phenyl, etc.; R1, R2, R3, R4, R6, R7, and R8 each represents hydrogen, C1-6 alkyl, etc.; R5 represents C1-6 alkyl, etc.; G represents NR10, etc.; W represents O, S, NR9, etc.; R9 and R10 each represents hydrogen, etc.; and n is an integer of 0-4)). The acetonitrile derivative is remarkably active in controlling pests even when used in a small dose. It is useful as an agricultural or horticultural bactericide or an animal parasite control agent.

Description

Specification

Acetonitrile derivatives, pest control agents and methods of use

[0001] The present invention relates to a acetonitrile derivative, a pest control agent containing the compound as an active ingredient, and a method of using the same.

Background art

[0002] Conventionally, it is known that certain types of acetonitrile derivatives are useful as pest control agents such as agricultural and horticultural insecticides and animal parasite control agents (see, for example, Patent Documents 1 to 5; ). However, any literature discloses acetonitrile derivative represented by the general formula (I) of the present application and its biological activity as a pest control agent.

Patent Document 1: Japanese Patent Laid-Open No. 2000-26392

Patent Document 2: Pamphlet of International Publication No. 02Z049641

Patent Document 3: Pamphlet of International Publication No. 02Z060257

Patent Document 4: International Publication No. 02Z102155 Pamphlet

Patent Document 5: International Publication No. 03Z042184 Pamphlet

Disclosure of the invention

Problems to be solved by the invention

[0003] Damage to pests, particularly pests and livestock in the field of agriculture and horticulture, and parasites in the field of pets, is due to factors such as the occurrence of pests or parasites resistant to large existing drugs. It is desired to develop a pest control agent having In addition, pesticides to be developed in the future are required to have the performance of being effective even at low doses, because they are highly safe for human livestock, and are easily decomposed in the environment and have a low environmental impact. Means for solving the problem

[0004] As a result of intensive research aimed at developing a novel pesticide that solves the above problems, the inventors of the present invention have developed a new acetonitrile derivative represented by the general formula (I) that is not described in any literature. The present invention was completed by finding that it is a compound and has a remarkable pest control effect. That is, the present invention relates to the general formula (I)

Formula (I)

{Where A is

Wherein Q ¹ is a (C—C) alkyl group, a halo (CC) alkyl group, (CC) cycloal

1 6 1 6 3 6

Kill group, halo (c -c) cycloalkyl group, phenol group, same or different

3 6

Logen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C) alkyl group, (

1 6 1 6

C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyl group, halo (

1 6 1 6 2 6

C C) alkyl group, (C C) alkyl group, (C C) cycloalkyl group, (C

2 6 2 6 3 6 2

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkyl group

6 2 6 1 6 thio group, halo (C—C) alkylthio group, (C—C) alkylsulfo-loxy group, ha

1 6 1 6

Mouth (C—C) alkyl sulfo-loxy group, (C—C) alkyl sulfier group, halo (

1 6 1 6

C—C) alkylsulfier group, (C—C) alkylsulfonyl group, halo (C—C) Alkylsulfol group, (C—C) alkylthio group, halo (C—C) alkenyl group

2 6 2 6

O group, (C—C) alkenylsulfuryl group, halo (C—C) alkulsulfyl group

2 6 2 6

Group, (C—C) alkenyl sulfonyl group, halo (C—C) alkenyl sulfonyl group,

2 6 2 6

(C—C) alkylamino group, same or different di (C—C) alkylamino group

1 6 1 6

Group, (C—C) alkylsulfonylamino, halo (C—C) alkylsulfonylamino

1 6 1 6

Group, (C C) alkylcarbonyl group, halo (C C) alkylcarbonyl group, (C

1 6 1 6 1

C) an alkyloxycarbonyl group, a phenyl group, a halogen atom which may be the same or different

6

Child, cyano group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C—C)

1 6 1 6 1 6

) Alkoxy group, halo (c—C) alkoxy group, (C—C) alkylthio group, halo (C

1 6 1 6 1

C) alkylthio, (C—C) alkylsulfinyl, halo (C—C) alkyls

6 1 6 1 6

Rufinyl group, (c—C 1) alkylsulfonyl group or halo (C—C 1) alkylsulfone

1 6 1 6 Group Basics Substitued phenyl group, phenoxy group, halogen atom, cyan group, nitro group, (C—C) alkyl group, which may be the same or different, having 1 to 5 substituents selected

1 6

, Halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group,

1 6 1 6 1 6

(C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo group

1 6 1 6 1 6

Finyl group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl

1 6 1 6

Having 1 to 5 substituents selected from a group or a halo (C C) alkylsulfonyl group

1 6

Substituted phenyl groups with 1 to 5 substituents selected, phenyl (C—C) alkyl groups, halogen atoms that may be the same or different, nitro groups, cyan groups

1 6

Group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo

1 6 1 6 1 6

(C C) alkoxy group, (C C) alkenyl group, halo (C C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

2 6 1 6 1 6 Kirthio group, (C—C) alkylsulfonyloxy group, halo (C—C) alkylsulfo group

1 6 1 6 Nyloxy group, (C—C) alkylsulfinyl group, halo (C—C) alkylsulfinyl group

1 6 1 6 Nyl group, (C—C) alkylsulfonyl group, halo (C—C) alkylsulfonyl group, (

1 6 1 6

C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C) alkenyl group

2 6 2 6 2 6

Rusulfinyl group, halo (C—C) alkenylsulfinyl group, (C—C) alkenyl

2 6 2 6 Sulfol group, halo (c-c) alkylsulfol group, mono (C—C) alkylamino

2 6 1 6

A di (C—C) alkylamino group, (C—C) alkylsulfide, which may be the same or different

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkyl carbo group, (C C) alkyloxy carbo-

1 6 1 6

Group, phenyl group, halogen atom which may be the same or different, cyan group, nitro group, (C —C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

6 1 6 1 6 1 to 5 selected from a kill sulfo group or a halo (C C) alkyl sulfo group

1 6

A substituted phenyl group, a phenoxy group, or the same or different, a halogen atom, a cyano group, a nitro group, a (C—C) alkyl group, a halo (C—C) alkyl group

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

1 6 1 6 1 6 Alkyl sulfier group, (C—C) alkyl sulfonyl group or halo (C—C) alkyl

1 6 1 6 Rusulfonyl group selected Substitued phenoxy group having 1 to 5 substituents selected Selected phenyl (CC) alkyl group having 1 to 5 substituents on the ring, phenoxy

1 6

(C—C) alkyl group, halogen atom, nitro group, and cyano group which may be the same or different

1 6

, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (

1 6 1 6 1 6

C—C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C) alkylene group

2 6 2 6 2 6 Rusulfinyl group, halo (C—C) alkenylsulfinyl group, (C—C) alkenyl

2 6 2 6

Sulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino

2 6 1 6

A di (C—C) alkylamino group, (C—C) alkylsulfide, which may be the same or different Honylamino group, halo (C 1 -c) alkylsulfonylamino group, (C—C) alkyl carbonyl

1 6 1 6

Ball group, halo (C C) alkylcarbol group, (C—C) alkyloxycarboxyl

1 6 1 6

Group, phenyl group, halogen atom which may be the same or different, cyan group, nitro group, (C —C) alkyl group, halo (C—C) alkyl group, (CC) alkoxy group, halo (C —C

6 1 6 1 6 1

) Alkoxy group, (c—C 1) alkylthio group, halo (C—C 1) alkylthio group, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (Cc) alkylsulfier group, (c-c) al

6 1 6 1 6 1-5 selected from a killylsulfonyl group or a halo (C 1 -C 6) alkylsulfonyl group

1 6

A substituted phenyl group, a phenoxy group, or the same or different, a halogen atom, a cyano group, a nitro group, a (c 1 -c) alkyl group, a halo (c 1 -c 3) alkyl group

1 6 1 6

, (C—C) alkoxy group, halo (c-c) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C C)

1 6 1 6 1 6 Alkylsulfinyl group, (c-c) alkylsulfonyl group or halo (C—C) alkyl

Selected from 1 6 1 6 norsulfonyl group

A substituted phenoxy group having 1 to 5 substituents, a substituted phenoxy (C—C) alkyl group having 1 to 5 substituents on the ring, a phenylamino group, the same or different

1 6

Halogen atom, nitro group, cyan group, (C—C

1 6) alkyl group, halo (C—C) a

1 6 alkyl, (C—C) alkoxy, halo (C—C) alkoxy, (C—C) alkenyl

1 6 1 6 2 6 group, halo (C—C) alkenyl group, (C—C) alkynyl group, (C—C) cycloalkenyl

2 6 2 6 3 6 group, (C—C) alkenyloxy group, halo (C—C) alkoxy group, (C—C

2 6 2 6 1 6

) Alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo-luo

1 6 1 6

Xyl group, halo (C—C) alkylsulfonyloxy group, (C—C) alkylsulfinyl

1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl group,

1 6 1 6

(C—C) alkylsulfonyl group, (C—C) alkylthio group, halo (C—C) a

1 6 2 6 2 6 Lucyruthio group, (C—C) alkenylsulfier group, halo (C—C) alkenyls

2 6 2 6

Rufinyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfo group

2 6 2 6 Nyl group, mono (C—C) alkylamino group, di (C—C) alkyl which may be the same or different

1 6 1 6 Killamino group, (C—C) alkylsulfonylamino group, halo (C—C) alkylsulfo group

1 6 1 6 Nylamino group, (C—C) alkylcarbonyl group, halo (CC) alkylcarbonyl group Group, (c -c) alkyloxycarbol group, phenol group, the same or different

1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

1 6 1 6 Rusulfol group selected Substitued fur group, phenoxy group, halogen atom, cyan group, nitro group which may be the same or different, having 1 to 5 substituents, (C— C)

16 alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C)

1 6 1 6 1 6 Lucoxy group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C)

1 6 1 6 1 6 Alkylsulfinyl group, halo (C—C) alkylsulfinyl group, (C—C) alkyl

1 to 6 selected from 1 6 1 6 rusulfonyl group or halo (C C) alkylsulfonyl group

1 6

A substituted phenylamino group having 1 to 5 substituents selected from a substituted phenoxy group having a substituent on the ring, an aromatic 6-membered heterocyclic group having 1 to 2 nitrogen atoms, or the same or different Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (

1 6

C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C −

1 6 1 6 1 6 2

C) alkenyloxy group, halo (c-c) alkenyloxy group, (C—C) alkylthio group

6 2 6 1 6

Group, halo (c -c) alkylthio group, (c -c) alkylsulfinyl group, halo (C

1 6 1 6 1

-C) alkylsulfinyl group, (C-C) alkenylthio group, halo (c-c) alkke

6 2 6 2 6 Diruthio, (C—C) alkenylsulfinyl, halo (c -c) alkenylsulfur

2 6 2 6

Ynyl group, (c -c) alkylsulfonyl group, halo (c -c) alkylsulfonyl group, (

1 6 1 6

c -c) alkenylsulfonyl group, halo (c -c) alkenylsulfonyl group, mono (C

2 6 2 6 1

— C) alkylamino group or di (C—C) alkylamino which may be the same or different

6 1 6

A substituted aromatic 6-membered heterocyclic group having 1 to 2 nitrogen atoms having one or more selected substituents.

R ¹ is a hydrogen atom, (CC) alkyl group, halo (CC) alkyl group, (CC) al

1 6 1 6 1 6 Coxy (c -c) alkyl group, (c -c) alkenyl group, halo (C—C) alkal group

1 6 2 6 2 6

, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkylcarbo

2 6 2 6 1 6

-Lole group, halo (C—C) alkylcarbol group, phenolecarol group, the same or different Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (CC

1 6 1

) Alkyl group, (C C) alkoxy group or halo (C C) alkoxy group

6 1 6 1 6

Substituted full-carbon group having 1 to 5 substituents, (C C) alkoxycal

1 6

A ball group or a halo (C C) alkoxycarbol group is shown. )

1 6

Or

(In the formula, Ar ¹ is a phenyl group, which may be the same or different, a nitro group, a cyan group, a (C—C) alkyl group, a halo (C—C) alkyl group, (C—C)) Alkoxy group, halo

1 6 1 6 1 6

(C—C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

— C) alkyl group, (C C) cycloalkyl group, (C—C) alkoxy group,

6 3 6 2 6

Halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C—C) al

2 6 1 6 1 6 Kirthio group, (C—C) alkyl sulfo-loxy group, halo (C—C) alkyl sulfo group

1 6 1 6

-Luoxy group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi group

1 6 1 6

Group, (C—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (

1 6 1 6

C—C) alkthio group, halo (C—C) alkthio group, (C—C) alkyl group

2 6 2 6 2 6

Rusulfyl group, halo (C—C) alkulsulfyl group, (C—C) alkenyl

2 6 2 6

Sulfol group, halo (C—C) alkaryl sulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C C) alkylsulfo-lamino group, (C—C) alkyl carbonyl

1 6 1 6

Ball group, halo (C C) alkylcarbol group, (C C) alkyloxycarboxyl

1 6 1 6

Group, phenyl group, halogen atom which may be the same or different, cyan group, nitro group, (C —C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C ) Alkoxy group, (c C) alkylthio group, halo (CC) alkylthio group, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (c-c) alkylsulfier group, (C—C) al

6 1 6 1 6 One or more selected from a kill sulfo group or a halo (C C) alkyl sulfo group

1 6

A substituted phenyl group having a substituent, a phenoxy group, or a halogen atom, cyan group, nitro group, (c -c) alkyl group, halo (c -c) alkyl group, which may be the same or different, (C

1 6 1 6

-c) alkoxy group, halo (c-c) alkoxy group, (c-c) alkylthio group, halo

1 6 1 6 1 6

(c -c) alkylthio group, (C—C) alkylsulfier group, halo (c -c) al

1 6 1 6 1 6 Killsulfier group, (C—C) alkylsulfol group or halo (c -c) alkyls

1 6 1 6

A substituted phenyl group having one or more substituents selected, a substituted phenyl group having one or more substituents selected, an aromatic 6-membered bicyclic group having 1 to 2 nitrogen atoms, or the same or Different halogen atoms, cyan groups, nitro groups, (C 1 -C 6) alkyl groups, halo (C 1 -C 6) alkyl groups, (C—C 1) alkoxy groups, halo (C—C 1)

6 1 6 1 6 1 6 Lucoxy group, (c -C) alkoxy group, halo (C—C) alkoxy group, (C

2 6 2 6

—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfi group

1 6 1 6 1 6

-Lu group, halo (C—C) alkylsulfier group, (C—C) alkylthio group, halo (

1 6 2 6

C—C) alkylthio group, (C—C) alkenylsulfier group, halo (C—C)

2 6 2 6 2 6 Lukesulfyl group, (C—C) alkylsulfol group, halo (C—C) alkyl

1 6 1 6 Sulfoyl group, (C—C) alkaryl sulpho group, halo (C—C) alkal sulpho group

2 6 2 6

-Group, mono (C—C) alkylamino group or di (C—C) which may be the same or different

1 6 1 6

) Alkylamino group power A substituted aromatic 6-membered heterocyclic group having 1 to 2 nitrogen atoms having one or more selected substituents.

G is NR ^1G (where R ^1G is a hydrogen atom, (C—C) alkyl group, halo (C—C) alkyl)

1 6 1 6

Group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkyl group

2 6 2 6 2 6

, Halo (C—C) alkyl group, (C—C) alkylthio group, halo (CI—C6) alkyl

2 6 1 6

Thio group, (C—C) alkyl carbo group, halo (C—C) alkyl carbo group, (

1 6 1 6

C—C) alkoxycarbonyl group or halo (C—C) alkoxycarbonyl group.

1 6 1 6

), A sulfur atom or a single bond.

R ² represents a hydrogen atom, a (C—C) alkyl group, a halo (C—C) alkyl group, a cyano (C—C

1 6 1 6 1 6 ) Alkyl group, (CC) alkyl group, halo (CC) alkenyl group, (CC)

2 10 2 10 2 10 Alkynyl group, halo (C C) alkynyl group, (C C) alkoxycarbonyl (C

2 10 1 6 1

— C) alkyl group, phenyl (C—C) alkyl group, halogens which may be the same or different

6 1 6

Atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C

1 6 1 6 1

— C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkoxyloxy group,

6 1 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

2 6 1 6 1 6 Kirthio group, (C—C) alkylsulfinyl group, halo (C—C) alkylsulfie group

1 6 1 6

Group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C)

2 6 2 6 2 6 Lucenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (C—C) al

2 6 1 6 Killsulfonyl group, /, (C C) alkylsulfoyl group, (C C) alkenylsulfur

1 6 2 6

Phonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino group

1 to 5 selected from 2 6 1 6 or the same or different di (C C) alkylamino groups

1 6

Substituted phenyl (C C) alkyl groups having 1 substituent on the ring, nitrogen atoms 1 to 2

1 6

Aromatic 6-membered heterocycle (C C) alkyl group or same or different

1 6

, Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) alkyl

1 6 1 6 group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyloxy

1 6 1 6 2 6

Si group, halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C

2 6 1 6 1 6

) Alkylthio group, (C—C) alkylsulfier group, halo (C—C) alkylsnole

1 6 1 6

Finyl group, (C—C) alkenylthio group, halo (C C) alkenylthio group, (C

2 6 2 6 2

C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (C—C)

6 2 6 1 6 Alkylsulfonyl group, halo (C—C) alkylsulfonyl group, (C—C) alkenyl

1 6 2 6

Sulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 or more selected from di (C—C) alkylamino groups which may be the same or different

1 6

A substituted aromatic 6-membered heterocyclic (C—C) alkyl group having 1 to 2 nitrogen atoms having the above substituent on the ring. ).

6

B is

(Wherein R ³ and R ⁴ may be the same or different hydrogen atoms, (C—C) alkyl groups,

1 6

Mouth (c -c) alkyl group, (c -c) cycloalkyl group or halo (c -c) cycloal

1 6 3 6 3 6

R ³ and R ⁴ together can form a (C—C) alkylene group.

2 6

wear.

R ⁵ is a (C 1 -C 6) alkyl group, a halo (C 1 -C 6) alkyl group, (C—C 1) cycloalkyl

1 6 1 6 3 6

Group, halo (c -C) cycloalkyl group, (C—C) alkenyl group, halo (C—C) al

3 6 2 10 2 10 Kale group, (C C) alkyl group, halo (C—C) alkyl group, (C C) alkyl

2 10 2 10 1 6 Xyl (C—C) alkyl group, (C—C) alkylthio (C—C) alkyl group, (C—C

1 6 1 6 1 6 1 6

) Alkylsulfiel (C—C) alkyl group, (C—C) alkylsulfol (C

1 6 1 6 1

C) alkyl group, (C—C) alkoxycarbole (C—C) alkyl group, phenol (C

6 1 6 1 6

—C) alkyl group, halogen atom, cyan group, nitro group, which may be the same or different, (

1 6

C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C

1 6 1 6 1 6 1

— C) alkoxy group, (C—C) alkenyloxy group, halo (C—C) alkenyloxy

6 2 6 2 6

Si group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyl

1 6 1 6 1 6 Rusulfinyl, halo (C—C) alkylsulfinyl, (C—C) alkenyl

1 6 2 6

Group, halo (C—C) alkenyl dithio group, (C—C) alkenylsulfinyl group, halo (

2 6 2 6

C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C—C)

2 6 1 6 1

) Alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkke

6 2 6 2 6 Nylsulfonyl group, mono (C—C) alkylamino group, or the same or different

1 6

Di (C—C) alkylamino group A substituted group having 1 to 5 selected substituents on the ring.

1 6 A carboxylic group (c -c), a carboxylic group (C-C), an alkyl group, the same or different

1 6 1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) a

1 6 1 6 alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyl group

1 6 1 6 2 6 Roxy group, halo (C—C) alkoxy group, (C—C) alkylthio group, halo (

2 6 1 6

C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) alkyl

1 6 1 6 1 6 Rusulfyl group, (C—C) alkylthio group, halo (C—C) alkylthio group,

2 6 2 6

(C—C) alksulfyl group, halo (C—C) alkulsulfyl group, (C

2 6 2 6 1

—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (C—C) al

6 1 6 2 6 Kalksulfol group, halo (C—C) alkylsulfol group, mono (C—C) alkyl

2 6 1 6 Lamino groups or di (C—C) alkylamino groups which may be the same or different

1 6

Substituted phenyl (C C) alkynyl groups having 1 to 5 substituents on the ring,

1 6

Ci (C—C) alkyl group, halogen atom, cyan group or nitro group which may be the same or different

1 6

, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (

1 6 1 6 1 6

C—C) alkoxy, (C—C) alkenyloxy, halo (C—C) alkenyl

1 6 2 6 2 6

Xyl, (C—C) alkylthio, halo (C—C) alkylthio, (C—C) al

1 6 1 6 1 6 Kill sulfinyl group, halo (C—C) alkylsulfinyl group, (C—C) alkenyl

1 6 2 6

Thio, halo (C—C) alkenylthio, (C—C) alkenylsulfinyl,

2 6 2 6

(C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C

2 6 1 6 1

—C) alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C—C) a

6 2 6 2 6 Lucenylsulfonyl group, mono (c—C) alkylamino group, or the same or different

1 6

Good di (C—C) alkylamino group with 1-5 substituents on the ring selected

1 6

Substituted phenoxy (c—C) alkyl group, phenylthio (C—C) alkyl group, identical or

1 6 1 6

Different halogen atoms, cyan groups, nitro groups, (C—C) alkyl groups, halo (C

1 6 1

— C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C)

6 1 6 1 6 2 6 Alkenyloxy group, halo (c—C) alkenyloxy group, (C—C) alkylthio group

2 6 1 6

Group, halo (C C) alkylthio group, (C C) alkylsulfinyl group, halo (C

1 6 1 6 1

C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C) alkenyl group

6 2 6 2 6 Ruthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group

2 6 2 6 -L group, (c -c) alkylsulfol group, halo (c -c) alkylsulfol group, (

1 6 1 6

c -c) alkenyl sulfol group, halo (C—C) alkenyl sulfol group, mono (C

2 6 2 6 1

6 1 6

Substituted phenylthio (C—C) alkyl having 1 to 5 selected substituents on the ring

1 6 Kill group, phenylsulfinyl (C—C) alkyl group, halo which may be the same or different

1 6

Gen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C

1 6 1 6

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyloxy group,

1 6 1 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

2 6 1 6 1 6 Kirthio group, (C—C) alkylsulfinyl group, halo (C—C) alkylsulfinyl group

1 6 1 6

Group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C)

2 6 2 6 2 6 Lucenyl sulfinyl group, halo (c—C) alkenyl sulfinyl group, (C—C) al

2 6 1 6 Killsulfonyl group, halo (C—C) alkylsulfonyl group, (C—C) alkenylsulfur group

1 6 2 6

Phonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino group

2 6 1 6 or di (C—C) alkylamino groups which may be the same or different 1 to 5 selected

1 6

Substituted phenylsulfinyl (C C) alkyl groups having one substituent on the ring, phenyl

1 6

Rusulfonyl (C—C) alkyl group, halogen atom which may be the same or different, cyan

1 6

Group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy

1 6 1 6 1 6 Si group, halo (C—C) alkoxy group, (C—C) alkenyloxy group, halo (C—C) group

1 6 2 6 2 6 Lucenyloxy group, (c—C) alkylthio group, halo (C—C) alkylthio group, (C

1 6 1 6 1

—C) alkylsulfinyl group, halo (C—C) alkylsulfinyl group, (C—C)

6 1 6 2 6 Alkenylthio group, halo (c—C) alkenyl thio group, (C—C) alkenylsulfide

2 6 2 6

Nyl group, halo (C C) alkenylsulfinyl group, (C C) alkylsulfonyl group

2 6 1 6

, Halo (C—C) alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C

1 6 2 6

—C) alkenylsulfonyl group, mono (C—C) alkylamino group, or the same or

2 6 1 6

Di (C—C) alkylamino group may be different 1 to 5 selected substituents on the ring

1 6

Substituted phenylsulfonyl (C C) alkyl group, phenylamino (C C)

1 6 1 6 alkyl group, halogen atom which may be the same or different, cyan group, nitro group, (C—C)

1 6 alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (C C) alkyl

1 6 1 6 1 6 Xy group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C

2 6 2 6 1

C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo-

6 1 6 1 6

Group, halo (C—C) alkylsulfier group, (C—C) alkenylthio group, halo (C

1 6 2 6

— C) alkylthio group, (C—C) alksulfyl group, halo (C

2 6 2 6 2

—C) alkylsulfyl group, (C—C) alkylsulfol group, halo (C—C)

6 1 6 1 6 Alkylsulfol group, (C—C) alkylsulfol group, halo (C—C) alkenyl group

2 6 2 6 rusulfol group, mono (C—C) alkylamino group

1 6

(C—C) alkylamino group substituted phenyl having 1 to 5 selected substituents on the ring

1 6

Nilamino (C C) alkyl group, phenylaminocarbonyl group or the same or different

1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C)

1 6 1 6 alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkke

1 6 1 6 2 6 Nyloxy group, halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo

2 6 1 6

(C—C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) al

1 6 1 6 1 6 Killsulfinyl group, (C C) alkenylthio group, halo (C C) alkenylthio group

2 6 2 6

, (C—C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (

2 6 2 6

C—C) alkylsulfonyl group, halo (C—C) alkylsulfonyl group, (C—C)

1 6 1 6 2 6 Lucenylsulfonyl, halo (C—C) alkenylsulfonyl, mono (C—C) al

2 6 1 6 selected from a killamino group or a di (C—C) alkylamino group which may be the same or different

1 6

And a substituted phenaminocarbo group having 1 to 5 substituents on the ring.

W is an oxygen atom, sulfur atom, SO—, —SO— or — NR ⁹ — (where R ⁹ is a hydrogen atom

2

Child, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkylcarbohydrate

1 6 1 6 1 6

Group, halo (C—C) alkylcarbonyl group, (C—C) alkoxy (C—C) alkyl

1 6 1 6 1 6 group or (C—C) alkoxycarbonyl group. R ⁹ is oxygenated with R ⁵

1 6

It can also form 5- to 8-membered rings which can be interrupted by atoms, sulfur atoms or nitrogen atoms. ). ),

(In the formula, Q ² represents (CC) alkyl group, halo (C alkyl group, phenyl group, same or

1 6 1 -C)

6

May be different from halogen atom, nitro group, cyano group, (C 1 -C 6) alkyl group, halo (

1 6 C

-C) alkyl group, (c -c) alkoxy group, halo (c 1 -c) alkoxy group, (

1 6 1 6 6 c 2 -c 6

) Alkenyl group, halo (c -c) alkenyl group, (group, (

2 6 c 2 -c) alkynyl

6 c 3 -c)

6 chloroalkyl group, (c -c) alkenyloxy group, halo (

2 6 c 2 -c) alkenyloxy group

6

, (C -c) alkylthio group, halo (c -c) alkylthio group, (c -c) alkyls

1 6 1 6 1 6

Sulfonyloxy group, halo (c -c) alkylsulfonyloxy group, (c alkyl

1 6 1 -c)

6 Sulfinyl group, halo (c-)

1 C) alkylsulfinyl group, (e 6 C 1—C alkylsulfinyl group)

6

Nyl group, halo (c-c) alkylsulfonyl group, (c-c) alkenylthio group, halo (

1 6 2 6

c -c) alkenyl dithio group, (c -c) alkenyl sulfinyl group, halo (c -c) a

2 6 2 6 2 6 Lucenylsulfiel group, (c -c) alkenylsulfonyl group, halo (c

2 6 2 -c)

6 Nylsulfonyl group, mono (C

1—C) alkylamino group, identical or

6 (C 1

-C) alkylamino group, (c-c) alkylsulfonylamino group, halo (c-c) al

6 1 6 1 6 Killsulphonylamino group, (C Bonyl group, Halo (

1—C) alkylcal

6 c 1 -c) alkyl

6 Carbonyl group, (C C) alkyloxycarbonyl group, phenyl group, the same or different

1 6

Any halogen atom, cyano group, nitro group, (C 1) alkyl group, halo (

1—c6 c 1 -c 6) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkyl

1 6 1 6 1 6 Ruthio group, halo (c -c) alkylthio group, (C—C) alkylsulfier group, halo

1 6 1 6

(C 1 -c) alkylsulfiel group, (C—C 1) alkylsulfol group or halo (C

1 6 1 6 1

C) an alkylsulfonyl group, a substituted phenyl group having 1 to 5 substituents selected A phenoxy group or the same or different, a halogen atom, a cyano group, a nitro group, a (c-c) alkyl group, a halo (c-c) alkyl group, a (c-c) alkoxy group, a halo (C

1 6 1 6 1 6 1

-C) alkoxy group, (c -c) alkylthio group, halo (c -c) alkylthio group, (C

6 1 6 1 6

-C) alkylsulfinyl group, halo (c-c) alkylsulfinyl group, (C—C)

1 6 1 6 1 6 selected from an alkylsulfonyl group or a halo (c-c) alkylsulfonyl group 1 to

1 6

Selected from substituted phenoxy groups having 5 substituents:! To a substituted phenyl group having 5 substituents, an aromatic 6-membered heterocyclic group having 1 to 2 nitrogen atoms, or the same or different Good halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C

1 6 1

-C) alkyl group, (c -c) alkoxy group, halo (c -c) alkoxy group, (C 1 C)

2 6 1 6

Group, halo (c -c) alkylthio group, (c -c) alkylsulfinyl group, halo (C 1

1 6 1 6 1 c) Alkylsulfier group, (c -c) alkenylthio group, halo (c -c) alkenyl group

6 2 6 2 6 Ruthio group, (c -c) alkenylsulfinyl group, halo (c -c) alkenylsulfinyl group

2 6 2 6

Nyl group, (c -c) alkylsulfonyl group, halo (c -c) alkylsulfonyl group, (

1 6 1 6

c -c) alkenylsulfonyl, halo (C -C) alkenylsulfonyl, mono (C

2 6 2 6 1

6 1 6

R ⁶ is a hydrogen atom, (C 1 C) alkyl group, (C 1 -C 6) cycloalkyl group, phenyl (C

1 6 3 6 1

-C) alkyl group, halogen atom which may be the same or different, cyan group, nitro group, (C

6 1

-C) alkyl group, halo (c -c) alkyl group, (c -c) alkoxy group, halo (c -c

6 1 6 1 6 1

) Alkoxy group, (C—C) alkenyloxy group, halo (C—C) alkenyloxy group

6 2 6 2 6

, (C 1 c) alkylthio group, halo (c -c) alkylthio group, (c -c) alkyls

1 6 1 6 1 6

Rufinyl group, halo (c -c) alkylsulfier group, (c -c) alkenylthio group

1 6 2 6

, Halo (c -c) alkenylthio group, (c -c) alkenylsulfinyl group, halo (C

2 6 2 6 2

-C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C—C)

6 1 6 1 6 Alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (c -c) alkenyl group

2 6 2 6 rusulfonyl group, mono (C—C) alkylamino group, or the same or different di- (C 1 -C 6) alkylamino group substituted phenyl having 1 to 5 selected substituents on the ring

1 6

-Lu (c -c) alkyl group, pyridyl (c -c) alkyl group or the same or different

1 6 1 6

Good halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) al

1 6 1 6 Kill group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyl

1 6 1 6 2 6 oxy group, halo (c -c) alkenyloxy group, (

2 6 c 1 -c) alkylthio group, halo (

6 C 1

-C) alkylthio group, (C—C) alkylsulfinyl group, halo (c -c) alkyl

6 1 6 1 6 Sulfinyl group, (c -C) alkenylthio group, halo (c -c) alkenylthio group, (

2 6 2 6 C

-C) alkenylsulfinyl group, halo (c-c) alkenylsulfinyl group, (

2 6 2 6 C 1

C) alkylsulfonyl group, halo (c-c) alkylsulfonyl group, (C—C) alkke

6 1 6 2 6 Nylsulfonyl group, halo (C C) alkenylsulfonyl group, mono (C C) alkyl

2 6 1 6 Amino group or di (C C) alkylamino group which may be the same or different

1 6

And a substituted pyridyl (C 1 -C 6) alkyl group having 1 to 4 substituents on the ring. )

1 6

Or

(Wherein R ³ , R ⁴ and W are the same as above, and R ⁷ and R ⁸ may be the same or different, a hydrogen atom, a (C—C 1) alkyl group, a halo (C 1 -C 6) alkyl group, (C—C) cycloalkyl

1 6 1 6 3 6

A group or a halo (c 3 -c) cycloalkyl group;

6

Ar ² is a phenyl group, halogen atom which may be the same or different, nitro group, cyan group, (C

-C) alkyl group, halo (c -c) alkyl group, (c -c) alkoxy group, halo (C

1 6 1 6 1 6 1

C) alkoxy group, (C C) alkenyl group, halo (C C) alkenyl group, (C C)

6 2 6 2 6 2 6 Alkyl group, (C—C) cycloalkyl group, (C—C) alkoxy group, halo (C -c) alkenyloxy, (C—C) alkylthio, halo (c-c) alkylthio

2 6 1 6 1 6

Group, (C—C) alkylsulfo-loxy group, halo (C—C) alkylsulfo-luo group

1 6 1 6

A xy group, a (C 1 c) alkylsulfyl group, a halo (c-c) alkylsulfiel group,

1 6 1 6

(C 1 C) alkylsulfonyl group, halo (C 1 C) alkylsulfonyl group, (C 1 C)

1 6 1 6 2 6 Alkenylthio group, halo (C—C) alkenylthio group, (C—C) alkenylsulfi

2 6 2 6

-Luyl group, halo (C—C) alkulsulfyl group, (C—C) alkenylsulfonyl

2 6 2 6

Group, halo (C 1 C) alkarylsulfol group, mono (C—C) alkylamino group, identical

2 6 1 6

Or a di (C—C) alkylamino group, which may be different, (C—C) alkylsulfuryl

1 6 1 6

Mino group, halo (C—C) alkylsulfonylamino group, (C—C) alkyl carbonyl group

1 6 1 6

, Halo (C—C) alkylcarbonyl group, (C—C) alkyloxycarbonyl group,

1 6 1 6

Phenyl group, same or different, halogen atom, cyano group, nitro group, (C 1 C) a

1 6 alkyl, halo (C—C) alkyl, (C—C) alkoxy, halo (C—C) alkyl

1 6 1 6 1 6 Xyl group, (C 1 C) alkylthio group, halo (C—C) alkylthio group, (C—C) al

1 6 1 6 1 6 Kill sulfier group, halo (C—C) alkyl sulfinyl group, (C—C) alkyl group

1 6 1 6

One or more substituents selected from a sulfonyl group or a halo (C 1 C) alkylsulfonyl group

1 6

Substituted phenyl group, phenoxy group or halogen atom, cyan group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C—C), which may be the same or different

1 6 1 6 1 6

) Alkoxy, halo (C—C) alkoxy, (C—C) alkylthio, halo (C 1

1 6 1 6 1

C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) alkyl group

6 1 6 1 6

Rufinyl group, (C—C) alkylsulfonyl group, or halo (C—C) alkylsulfoni

1 6 1 6 group selected substituted phenoxy group having one or more substituents selected substituted phenyl group having one or more substituents selected, aromatic 6-membered heterocycle having 1 to 2 nitrogen atoms A halogen atom, cyano group, nitro group, (C—C) a which may be the same or different

1 6 alkyl, halo (C—C) alkyl, (C—C) alkoxy, halo (C—C) alkyl

1 6 1 6 1 6 xy group, (C 1 C) alkenyloxy group, halo (C—C) alkenyloxy group, (C 1

2 6 2 6 1

C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfini

6 1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C

1 6 2 6

—C) alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) al

2 6 2 6 2 6 Kenylsulfuryl group, (C—C) alkylsulfol group, halo (c -c) alkyls

1 6 1 6

Ruphorol group, (C—C) alkarylsulfol group, halo (C—C) alkylsulfol group

2 6 2 6

Group, mono (C—C) alkylamino group or di (C—C) which may be the same or different

1 6 1 6 Alkylamino group power A substituted aromatic 6-membered heterocyclic group having 1 or 2 nitrogen atoms having one or more selected substituents. n represents 0 or an integer of 1 to 4. ).

R is a hydrogen atom, (C C) alkyl group, halo (C C) alkyl group, (C C) cyclo

1 6 1 6 3 6 Alkyl group, halo (C—C) cycloalkyl group, (C—C) alkenyl group, halo (C

3 6 2 10 2

C) alkyl group, (C—C) alkyl group, halo (C—C) alkyl group, (C

10 2 10 2 10 1

C) alkoxycarbol (C—C) alkyl group, phenol (C—C) alkyl group or

6 1 6 1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl, which may be the same or different

1 6 groups, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group

1 6 1 6 1 6

, (C—C) alkenyloxy group, halo (C—C) alkenyloxy group, (C—C)

2 6 2 6 1 6 alkylthio group, halo (C C) alkylthio group, (C C) alkylsulfinyl group,

1 6 1 6

Halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C

1 6 2 6 2 6

) Alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyl group

2 6 2 6 Rusulfinyl group, (C—C) alkylsulfonyl group, halo (C—C) alkylsulfo group

1 6 1 6

Nyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group

2 6 2 6

A mono (C—C) alkylamino group or the same or different di (C—C) al

1 6 1 6 Kiramino group Substitued phenyl (C C) having 1 to 5 substituents on the ring selected

1 6 represents an alkyl group. } For the acetonitrile derivative

For further details, refer to the general formula (I 1)

{Wherein Q ¹ is a (C—C) alkyl group, halo (C—C group, (CC Kill group, halo (c -c) cycloalkyl group, phenol group, same or different

3 6

1 6 1 6

C—C) alkoxy, halo (C—C) alkoxy, (C—C) alkenyl, halo (

1 6 1 6 2 6

C C) alkyl group, (C C) alkyl group, (C C) cycloalkyl group, (C

2 6 2 6 3 6 2

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkyl group

1 6 1 6

Mouth (C—C) alkyl sulfo-loxy group, (C—C) alkyl sulfier group, halo (

1 6 1 6

C—C) alkylsulfier group, (C—C) alkylsulfonyl group, halo (C—C)

1 6 1 6 1 6 Alkylsulfonyl group, (C—C) alkylthio group, halo (C—C) alkyl group

2 6 2 6

O group, (C—C) alkenylsulfuryl group, halo (C—C) alkulsulfyl group

2 6 2 6

Group, (C—C) alkenyl sulfonyl group, halo (C—C) alkenyl sulfonyl group,

2 6 2 6

(C—C) alkylamino group, same or different di (C—C) alkylamino group

1 6 1 6

Group, (C—C) alkylsulfonylamino, halo (C—C) alkylsulfonylamino

1 6 1 6

Group, (C C) alkylcarbonyl group, halo (C C) alkylcarbonyl group, (C

1 6 1 6 1

6

1 6 1 6 1 6

) Alkoxy group, halo (c—C) alkoxy group, (C—C) alkylthio group, halo (C

1 6 1 6 1

C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) alkyls

6 1 6 1 6

Rufinyl group, (c—C 1) alkylsulfonyl group or halo (C—C 1) alkylsulfone

1 6

, Halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group,

1 6 1 6 1 6

(C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo group

1 6 1 6 1 6

Finyl group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl

1 6 1 6

1 6

Group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo

1 6 1 6 1 6 (C 1 C) alkoxy group, (C 1 C) alkenyl group, halo (C 1 C) alkenyl group, (C

1 6 2 6 2 6 2

— C)) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

2 6 1 6 1 6 Kirthio group, (C 1 C) alkylsulfonyloxy group, halo (C 1 C) alkylsulfo group

1 6 1 6

-Luoxy group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi group

1 6 1 6

Group, (C—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (

1 6 1 6

C—C) alkenylthio group, halo (C—C) alkthio group, (C—C) alkenyl group

2 6 2 6 2 6

Rusulfier group, halo (C—C) alkenylsulfier group, (C—C) alkenyl

2 6 2 6

Sulfonyl group, halo (C—C) alkylenosulfonyl group, mono (C—C) alkylamino

2 6 1 6

A di (C 1 C) alkylamino group, which may be the same or different, (C—C) alkyl

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkyl carbonyl

1 6 1 6

Ball group, halo (C—C) alkylcarbonyl group, (C—C) alkyloxycarboxyl

1 6 1 6

Group, phenyl group, halogen atom which may be the same or different, cyan group, nitro group, (C —C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C One C

6 1 6 1 6 1

) Alkoxy, (C—C) alkylthio, halo (C—C) alkylthio, (C 1

6 1 6 1 6 1

C) alkylsulfinyl group, halo (C—C) alkylsulfinyl group, (C—C) al

6 1 6 1 6 1-5 selected from a killylsulfonyl group or a halo (C—C) alkylsulfonyl group

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio, (C 1 C) alkylsulfinyl, halo (C—C)

1 6 1 6 1 6 Alkylsulfinyl group, (C—C) alkylsulfonyl group or halo (C—C) alkyl

1 6 1 6 Rusulfonyl group selected Substitued phenoxy group having 1 to 5 substituents selected Substitued phenyl (C—C) alkyl group having 1 to 5 substituents on the ring, phenoxy

1 6

Ci (C-C) alkyl group, halogen atom, nitro group, and cyano group which may be the same or different

1 6

, (C -c) alkyl group, halo (c -c) alkyl group, (c -c) alkoxy group, halo (

1 6 1 6 1 6

c -c) alkoxy group, (c -c) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

-C) alkyl group, (c-c) cycloalkyl group, (c-c) alkenyloxy group,

6 3 6 2 6 Halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

-Luoxy group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi group

1 6 1 6

Group, (C—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (

1 6 1 6

C—C) alkthio group, halo (C—C) alkthio group, (C—C) alkyl group

2 6 2 6 2 6

Rusulfyl group, halo (C—C) alkulsulfyl group, (C—C) alkell

2 6 2 6

Sulfol group, halo (C—C) alkaryl sulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkyl carbo group, (C C) alkyloxy carbo-

1 6 1 6

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

Selected from 1 6 1 6 rusulfonyl group

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C) a

1 6 1 6 2 6 group, halo (C C) alkenyl group, (C C) alkynyl group, (C C) cycloalkyl

2 6 2 6 3 6 group, (C—C) alkenyloxy group, halo (C—C) alkenyloxy group, (C—C

2 6 2 6 1 6

) Alkylthio, halo (C—C) alkylthio, (C—C) alkylsulfonyl

1 6 1 6 Xyl group, halo (c—C) alkylsulfuroxy group, (C—C) alkylsulfi-

1 6 1 6

Group, halo (c -C) alkylsulfiel group, (C—C) alkylsulfol group,

1 6 1 6

(C—C) alkylsulfol group, (C—C) alkylthio group, halo (C—C) a

1 6 2 6 2 6 Lucenyl thio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyls

2 6 2 6

Rufinyl group, (C—C) alkenylsulfonyl group, halo (c -c) alkenylsulfo

2 6 2 6

-Lu group, mono (C—C) alkylamino group, di (C—C) alkyl which may be the same or different

1 6 1 6 Killamino group, (C—C) alkylsulfo-lumino group, halo (C—C) alkylsulfo group

1 6 1 6

-Luamino group, (C—C) alkylcarbonyl group, halo (C—C) alkylcarbonyl

1 6 1 6

Group, (C 1 C) alkyloxycarbol group, phenol group, which may be the same or different,

1 6

Halogen atom, cyano group, nitro group, (c -c) alkyl group, halo (C—C) alkyl group

1 6 1 6

(C—C) alkoxy group, halo (c-c) alkoxy group, (C-C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C-C) alkylsulfier group, halo (C—C)

1 6 1 6 A substituted phenyl group having 1 to 5 substituents selected from a rusulfonyl group, a phenoxy group, or a halogen atom, a cyan group, a nitro group, which may be the same or different, (C 1-C 6 ) Alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) a

1 6 1 6 1 6 Lucoxy group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) group

1 to 6 selected from 1 6 1 6 rusulfonyl group or halo (C—C 1) alkylsulfonyl group

1 6

A substituted phenamino group having 1 to 5 substituents selected from a substituted phenoxy group having a substituent on the ring, an aromatic 6-membered heterocyclic group having 1 to 2 nitrogen atoms, or the same or the same Different halogen atoms, cyano groups, nitro groups, (C 1-C) alkyl groups, halo (

6

C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C −

1 6 1 6 1 6 2

C) alkyloxy group, halo (c-c) alkoxy group, (C—C) alkylthio

6 2 6 1 6

Group, halo (c

1 -c) alkylthio group, (C—C) alkylsulfier group, halo (C 6 1 6 1

—C) alkylsulfinyl group, (C 1 C) alkylthio group, halo (C—C) alkke

6 2 6 2 6 Diruthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenylsulfur group

2 6 2 6

Ynyl group, (C—C) alkylsulfoyl group, halo (C—C) alkylsulfonyl group, (

1 6 1 6 c-c) alkaryl sulfonyl group, halo (C—C) alkaryl sulfonyl group, mono (C

2 6 2 6 1

6 1 6

R is a hydrogen atom, (C C) alkyl group, halo (C C) alkyl group, (C C) cyclo

3 6 2 10 2

C) alkyl group, (C—C) alkyl group, halo (C—C) alkyl group, (C

10 2 10 2 10 1

C) alkoxycarbol (C—C) alkyl group, phenol (C—C) alkyl group or

6 1 6 1 6

1 6 1 6 1 6

, (C—C) alkenyloxy, halo (C—C) alkenyloxy, (C—C)

1 6 1 6

Halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C

1 6 2 6 2 6

) Alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyl group

2 6 2 6

Rusulfinyl group, (C—C) alkylsulfonyl group, halo (C—C) alkylsulfo group

1 6 1 6

Nyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group

2 6 2 6

A mono (C—C) alkylamino group or the same or different di (C—C) al

1 6 represents an alkyl group.

R ¹ is a hydrogen atom, (CC) alkyl group, halo (CC) alkyl group, (CC) al

1 6 1 6 1 6 Coxy (C—C) alkyl group, (C—C) alkenyl group, halo (C—C) alkenyl group

1 6 2 6 2 6

, (C—C) alkynyl group, halo (C—C) alkynyl group, (C—C) alkylcarbo

2 6 2 6 1 6

Nyl group, halo (C C) alkylcarbonyl group, phenylcarbonyl group, the same or different

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C)

1 6 1

) Alkyl group, (C C) alkoxy group or halo (C C) alkoxy group

6 1 6 1 6

A substituted phenylcarbonyl group having 1 to 5 substituents, (C C) alkoxycal

1 6

A bonyl group or a halo (C C) alkoxycarbonyl group is shown.

1 6

R ³ and R ⁴ may be the same or different hydrogen atom, (C—C) alkyl group, halo (C

1 6 1 -c) alkyl group, (c-c) cycloalkyl group or halo (c-c) cycloalkyl group

6 3 6 3 6

R ³ and R ⁴ may be joined together to form a (C—C) alkylene group.

2 6

R ⁵ is (C 1 -C 6) alkyl group, halo (C 1 -C 6) alkyl group, (C 1 -C 6) cycloalkyl

1 6 1 6 3 6

Group, halo (C C) cycloalkyl group, (C C) alkenyl group, halo (C C) al

3 6 2 10 2 10 Kenyl group, (c -c) alkynyl group, halo (c -c) alkynyl group, (c -c) alkyl

2 10 2 10 1 6 Xyl (C C) alkyl group, (C C) alkylthio (C C) alkyl group, (C C

1 6 1 6 1 6 1 6

) Alkylsulfinyl (c -c) alkyl group, (C 1 -C) alkylsulfonyl (

1 6 6 C 1 c) alkyl group, (c -c) alkoxycarbonyl (c -c) alkyl group, phenyl (

6 1 6 1 6 C

-c) alkyl group, halogen atom, cyano group, nitro group, which may be the same or different, (

1 6

C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C

1 6 1 6 1 6 1

— C) alkoxy group, (C—C) alkenyloxy group, halo (C—C) alkenyloxy

6 2 6 2 6

Si group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyl

1 6 1 6 1 6 Rusulfinyl, halo (C—C) alkylsulfinyl, (C—C) alkenyl

1 6 2 6

Group, halo (C—C) alkenyl dithio group, (C—C) alkenylsulfinyl group, halo (

2 6 2 6

C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C—C)

2 6 1 6 1

) Alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkke

1 6

Phenyl (C—C) alkenyl group, phenyl (C—C) alkynyl group, the same or different

1 6 1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) a

1 6 1 6 alkyl, (C—C) alkoxy, halo (C—C) alkoxy, (C—C) alkenyl

1 6 1 6 2 6 Roxy group, halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (

2 6 1 6

C—C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) alkyl

1 6 1 6 1 6 Rusulfinyl group, (C C) alkenylthio group, halo (C C) alkenylthio group,

2 6 2 6

(C—C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (C

2 6 2 6 1 C) alkylsulfonyl group, halo (C C) alkylsulfonyl group, (C C) al

6 1 6 2 6 Kenylsulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkyl

1 6 Substituted phenol (CC) alkyl group having 1 to 5 substituents on the ring, phenoxy

1 6

, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (

1 6 1 6 1 6

C—C) alkoxy, (C—C) alkenyloxy, halo (C—C) alkenyl

1 6 2 6 2 6

Xyl, (C—C) alkylthio, halo (C—C) alkylthio, (C—C) al

1 6 2 6

Thio, halo (C—C) alkenylthio, (C—C) alkenylsulfinyl,

2 6 2 6

(C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C

2 6 1 6 1

—C) alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C—C) a

1 6

Good di (C—C) alkylamino group with 1-5 substituents on the ring selected

1 6

1 6 1 6

1 6 1

— C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C)

2 6 1 6

Group, halo (C C) alkylthio group, (C C) alkylsulfinyl group, halo (C

1 6 1 6 1

C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C) alkenyl group

2 6 2 6

Nyl group, (C—C 1) alkylsulfonyl group, halo (C—C 1) alkylsulfonyl group, (

1 6 1 6

C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C

2 6 2 6 1

6 1 6

1 6

1 6 1 6

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyloxy group,

1 6 1 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

Group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C) Luke-Lulsulfininole group, halo (c—C) alkenolinole norefier group, (C—C) anole

2 6 1 6 Killsulfol group, halo (C—C) alkylsulfonyl group, (C—C) alkylsulfur group

1 6 2 6

Hole group, halo (c -c) alkaryl sulfol group, mono (C—C) alkylamino group

2 6 1 6 or di (C—C) alkylamino group which may be the same or different 1 to 5 selected

1 6

Substituted phenylsulfinyl (C 1 C) alkyl groups having two substituents on the ring, phenyl

1 6

1 6 2 6 2 6 Luke-Loxy group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C

1 6 1 6 1 1 C) alkylsulfinyl group, halo (C 1 C) alkylsulfinyl group, (C 1 C)

2 6 2 6

Nyl group, halo (C—C) alkenolinolesulfier group, (c -c) alkylsulfonyl group

2 6 1 6

, Halo (C 1 C) alkylsulfonyl group, (C 1 C) alkenylsulfonyl group, halo (C

1 6 2 6

—C) alkenylsulfonyl group, mono (C—C) alkylamino group, or the same or

2 6 1 6

Di (C 1 C) alkylamino groups that may be different Select 1-5 substituents on the ring

1 6

Substituted phenylsulfonyl (C—C) alkyl group, phenylamino (C—C)

1 6 alkyl, halo (C—C) alkyl, (C—C) alkoxy, halo (C—C) alkyl

1 6 1 6 1 6 Xoxy group, (C—C) alkenyloxy group, halo (C—C) alkoxy group, (C—

2 6 2 6 1

C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfini

6 1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C 1 C) alkenylthio group, halo (C

1 6 2 6

—C) alkenyl thio group, (C—C) alkenyl sulfinyl group, halo (C

2 6 2 6 2 1 C) alkenylsulfinyl group, (C 1 C) alkylsulfonyl group, halo (C 1 C)

6 1 6 1 6 Alkylsulfonyl group, (C 1 C) alkenylolsulfonyl group, halo (C—C) alkenyl group

2 6 2 6 rusulfonyl group, mono (C—C) alkylamino group, or the same or different di-

1 6

(C 1 C) alkylamino group Substituent phenyl having 1 to 5 selected substituents on the ring

1 6

Nilamino (C 1 C) alkyl group, phenylaminocarbonyl group, or the same or different

1 6

A halogen atom, cyano group, nitro group, (C 1, halo (

1 C) alkyl group

6 C 1— C 6) Alkyl group, (c -c) alkoxy group, halo (c -c) alkoxy group, (c -c) alkke

1 6 1 6 2 6

-Luoxy group, halo (c -c) alkoxy-oxy group, (C—C) alkylthio group, halo

2 6 1 6

(C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) al

1 6 1 6 1 6 Killsulfier group, (C C) alkylthio group, halo (C C) alkylthio group

2 6 2 6

, (C—C) alkulsulfyl group, halo (C—C) alkulsulfyl group, (

2 6 2 6

C—C) alkylsulfol group, halo (C—C) alkylsulfonyl group, (C—C)

1 6 1 6 2 6 Alkylsulfol group, halo (C—C) alkenylsulfol group, mono (C—C) al

1 6

And a substituted phenaminocarbo group having 1 to 5 substituents on the ring.

2

Child, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkylcarbohydrate

1 6 1 6 1 6

Group, halo (C—C) alkylcarbonyl group, (C—C) alkoxy (C—C) alkyl

1 6

It can also form 5- to 8-membered rings which can be interrupted by atoms, sulfur atoms or nitrogen atoms. ). } Acetonitrile derivative represented by

Formula (I 2)

{Wherein Q ¹ is a (C—C) alkyl group, a halo (C—C) alkyl group, (C—C) cycloal

1 6 1 6 3 6

Kill group, halo (C—C) cycloalkyl group, phenol group, the same or different

3 6

1 6 1 6

C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyl group, halo (

1 6 1 6 2 6

CC) alkyl group, (CC) alkyl group, (CC) cycloalkyl group, (C -c) alkyloxy group, halo (C—C) alkoxy group, (C—C) alkyl

1 6 1 6

Mouth (C—C) alkyl sulfo-loxy group, (C—C) alkyl sulfier group, halo (

1 6 1 6

C—C) alkylsulfier group, (C—C) alkylsulfonyl group, halo (C—C)

2 6 2 6

O group, (C—C) alkenylsulfuryl group, halo (C—C) alkulsulfyl group

2 6 2 6

Group, (C—C) alkenyl sulfonyl group, halo (C—C) alkenyl sulfonyl group,

2 6 2 6

(C—C) alkylamino group, same or different di (C—C) alkylamino group

1 6 1 6

Group, (C—C) alkylsulfonylamino, halo (C—C) alkylsulfonylamino

1 6 1 6

Group, (C C) alkylcarbonyl group, halo (C C) alkylcarbonyl group, (C

1 6 1 6 1

6

1 6 1 6 1 6

) Alkoxy group, halo (c—C) alkoxy group, (C—C) alkylthio group, halo (C

1 6 1 6 1

C) alkylthio, (C—C) alkylsulfinyl, halo (C—C) alkyls

6 1 6 1 6

Rufinyl group, (c—C 1) alkylsulfonyl group or halo (C—C 1) alkylsulfone

1 6

, Halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group,

1 6 1 6 1 6

(C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo group

1 6 1 6 1 6

Finyl group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl

1 6 1 6

1 6

Group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo

1 6 1 6 1 6

(C C) alkoxy group, (C C) alkenyl group, halo (C C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6 -Luoxy group, (c-c) alkylsulfier group, halo (c -c) alkylsulfi group

1 6 1 6

-L group, (c -c) alkylsulfol group, halo (c -c) alkylsulfol group, (

1 6 1 6

c -c) alkthio group, halo (C—C) alkthio group, (C—C) alkoxy group

2 6 2 6 2 6 Rusulfyl group, halo (C—C) alkulsulfyl group, (C—C) alkenyl

2 6 2 6

Sulfol group, halo (C—C) alkaryl sulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkylcarbol group, (C C) alkyloxycarboxyl

1 6 1 6

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

1 6

, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (

1 6 1 6 1 6

C—C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6 c -c) alkthio group, halo (C—C) alkthio group, (C—C) alkoxy group

2 6 2 6 2 6

Rusulfyl group, halo (C—C) alkulsulfyl group, (C—C) alkenyl

2 6 2 6

Sulfol group, halo (C—C) alkaryl sulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkylcarbol group, (C C) alkyloxycarboxyl

1 6 1 6

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

1 6 1 6 1 6 Alkylsulfier group, (C—C) alkylsulfol group or halo (C—C) alkyl

Selected from 1 6 1 6 rusulfonyl group

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C) a

1 6 1 6 alkyl, (C—C) alkoxy, halo (C—C) alkoxy, (C—C) alkenyl

2 6 2 6 1 6

) Alkylthio, halo (C—C) alkylthio, (C—C) alkylsulfonyl

1 6 1 6

Xyl group, halo (C—C) alkylsulfonyloxy group, (C—C) alkylsulfinyl

1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl group,

1 6 1 6

(C—C) alkylsulfonyl group, (C—C) alkylthio group, halo (C—C) a

1 6 2 6 2 6 alkenylsulfinyl group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyls

2 6 2 6 Rufyl group, (c—C) alkaryl sulfol group, halo (C—C) alkulsulfol

2 6 2 6

-L group, mono (C—C) alkylamino group, di (C—C) al which may be the same or different

1 6 1 6

-Lumino group, (C C) alkyl carbo group, halo (C C) alkyl carbo group

1 6 1 6

Group, (C—C) alkyloxycarbonyl group, phenol group, the same or different

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

16 alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C)

1 to 6 selected from 1 6 1 6 rusulfonyl group or halo (C C) alkylsulfonyl group

1 6

C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C −

1 6 1 6 1 6 2

C) alkenyloxy group, halo (c-c) alkenyloxy group, (C—C) alkylthio group

6 2 6 1 6

Group, halo (c -c) alkylthio group, (c -c) alkylsulfinyl group, halo (C

1 6 1 6 1

-C) alkylsulfinyl group, (C-C) alkenylthio group, halo (c-c) alkke

6 2 6 2 6 Diruthio, (C—C) alkenylsulfinyl, halo (c -c) alkenylsulfur

2 6 2 6

Ynyl group, (c -c) alkylsulfonyl group, halo (c -c) alkylsulfonyl group, (

1 6 1 6

c -c) alkenylsulfonyl group, halo (c -c) alkenylsulfonyl group, mono (C

2 6 2 6 1

6 1 6

A substituted aromatic 6-membered heterocyclic group having 1 to 2 nitrogen atoms having one or more selected substituents. Q ² is a (C-C) alkyl group, a halo (C-C) alkyl group, a phenyl group, the same or different.

1 6 1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C)

1 6 1 6 alkyl group, (c -c) alkoxy group, halo (c -c) alkoxy group, (c -c) alkke

1 6 1 6 2 6

-Luyl group, halo (C-C) alkenyl group, (C-C) alkynyl group, (C-C) cycloa

2 6 2 6 3 6 alkyl group, (c) alkenyloxy group, halo (C—C) al

2 -c kenyloxy group, (C 6 2 6 1

—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo group

6 1 6 1 6

Luoxy group, halo (C—C) alkylsulfonyloxy group, (C—C) alkylsulfur group

1 6 1 6

Ynyl, halo (C—C) alkylsulfinyl, (C—C) alkylsulfonyl

1 6 1 6

, Halo (C-C) alkylsulfonyl group, (C-C) alkenylthio group, halo (C-C

1 6 2 6 2 6

) Alkenylthio group, (C—C) alkenylsulfier group, halo (C—C) alkenyl group

2 6 2 6 Rusulfiel group, (C—C) alkenylsulfonyl group, halo (C—C) alkenyls

2 6 2 6

Sulfonyl group, mono (C—C) alkylamino group, di (C—C) which may be the same or different

1 6 1 6 Alkylamino, (C—C) alkylsulfonylamino, halo (C—C) alkyls

1 6 1 6

Ruphonylamino group, (C—C) alkylcarbonyl group, halo (C—C) alkylcarbo group

1 6 1 6

Nyl group, (C 1 C) alkyloxycarbonyl group, phenyl group, the same or different

1 6

1 6 1 6 kill group, (C 1 C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkyl group

1 6 1 6 1 6o group, halo (C—C) alkylthio group, (C—C) alkylsulfinyl group, halo (C

1 6 1 6 1

—C 1) alkylsulfinyl group, (C 1 C) alkylsulfonyl group or halo (C—C 1)

6 1 6 1 6 Alkylsulfoyl group is selected from:! To 5 substituted phenyl groups, phenoxy groups, or halogen atoms, cyan groups, nitro groups, which may be the same or different. , (C —C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C

6 1 6 1 6 1

) Alkoxy, (C—C) alkylthio, halo (C—C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfinyl group, halo (C-C) alkylsulfinyl group, (C—C) al

1 6

A substituted phenoxy group having one or more substituents, a selected substituted phenyl group having 1 to 5 substituents, an aromatic 6-membered heterocyclic group having 1 to 2 nitrogen atoms, or a halogen which may be the same or different Atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C)

1 6 1 6 2 6

-Luoxy group, halo (c -c) alkoxy-oxy group, (C—C) alkylthio group, halo

2 6 1 6

(C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) al

2 6 2 6

, (C—C) alkulsulfyl group, halo (C—C) alkulsulfyl group, (

2 6 2 6

C—C) alkylsulfol group, halo (C—C) alkylsulfonyl group, (C—C)

1 6

And a substituted aromatic 6-membered heterocyclic group having 1 or 2 nitrogen atoms having one or more substituents.

R is a hydrogen atom, (C C) alkyl group, halo (C C) alkyl group, (C C) cyclo

3 6 2 10 2

C) alkyl group, (C—C) alkyl group, halo (C—C) alkyl group, (C

10 2 10 2 10 1

C) alkoxycarbol (C—C) alkyl group, phenol (C—C) alkyl group or

6 1 6 1 6

1 6 1 6 1 6

, (C—C) alkenyloxy group, halo (C—C) alkenyloxy group, (C—C)

1 6 1 6

Halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C

1 6 2 6 2 6

) Alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyl group

1 6 1 6

Nyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group

2 6 2 6

A mono (C—C) alkylamino group or the same or different di (C—C) al

1 6 represents an alkyl group.

R ¹ is a hydrogen atom, (CC) alkyl group, halo (CC) alkyl group, (CC) al

1 6 2 6 2 6

, (C—C) alkynyl group, halo (C—C) alkynyl group, (C—C) alkylcarbo

2 6 2 6 1 6 -Lole group, halo (c -c) alkylcarbol group, phenolecarol group, the same or different

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C)

1 6 1

) Alkyl group, (C C) alkoxy group or halo (C C) alkoxy group

6 1 6 1 6

Substituted full-carbon group having 1 to 5 substituents, (C C) alkoxycal

1 6

A ball group or a halo (C C) alkoxycarbol group is shown.

1 6

R ⁶ is a hydrogen atom, (C—C) alkyl group, (C—C) cycloalkyl group, phenol (C

1 6 3 6 1

—C) alkyl group, halogen atom which may be the same or different, cyan group, nitro group, (C

6 1 C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (C C

6 1 6 1 6 1

) Alkoxy group, (c—C) alkenyloxy group, halo (C—C) alkenyloxy group

6 2 6 2 6

, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyl group

1 6 1 6 1 6

Rufinyl group, halo (C C) alkylsulfinyl group, (C C) alkenylthio group

1 6 2 6

, Halo (C—C) alkenylsulfonyl group, (C—C) alkenylsulfinyl group, halo (C

2 6 2 6 2

—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C—C)

6 1 6 1 6 Alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenyl group

2 6 2 6 rusulfonyl group, mono (C—C 1) alkylamino group, or the same or different di groups

1 6

-L (C—C) alkyl group, pyridyl (C—C) alkyl group or the same or different

1 6 1 6

1 6 1 6 2 6 oxy group, halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C

2 6 1 6 1

—C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) alkyl

6 1 6 1 6 Sulfinyl group, (c—C) alkenyl thio group, halo (C—C) alkenyl thio group, (C

2 6 2 6

—C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (C

2 6 2 6 1

C) alkylsulfonyl group, halo (C—C) alkylsulfonyl group, (C—C) alkke

6 1 6 2 6 Nylsulfonyl group, halo (C C) alkenylsulfonyl group, mono (C C) alkyl

1 6

A substituted pyridyl (C—C) alkyl group having 1 to 4 substituents on the ring.

1 6

R and R ⁶ together — X ¹ — X ² — (where X ¹ and X ² may be the same or different. , A carbonyl group, a (CC) alkylene group or a halogen which may be the same or different

1 6

Atom, cyano group, nitro group, (C—C) alkoxy group, halo (C—C) alkoxy group, phenol

1 6 1 6

-Group, halogen atom, cyan group, nitro group, (c -c) al which may be the same or different

1 6 Kill group, halo (c -c) alkyl group, (c -c) alkoxy group or halo (c -c) al

1 6 1 6 1 6 Coxyl group power A substituted phenol group having 1 to 5 substituents, a pyridyl group, or a halogen atom, cyan group, nitro group, which may be the same or different, (C—C Alkyl)

16 groups, halo (C—C) alkyl groups, (C—C) alkoxy groups or halo (C—C) alkoxy groups

1 6 1 6 1 6 represents a substituted (C—C 1) alkylene group having one or more substituents selected from substituted pyridyl groups having 1 to 4 substituents selected from Si groups. 5-8 membered ring represented by

1 6

I'll do it for you. }

Acetonitrile derivative represented by:

General formula (I 3)

{In the formula, Ar ¹ is a phenyl group, which may be the same or different, a halogen atom, a nitro group, a cyan group, a (C—C) alkyl group, a halo (C—C) alkyl group, (C—C) Alkoxy group, halo

1 6 1 6 1 6

(C—C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

— C) alkyl group, (C C) cycloalkyl group, (C—C) alkoxy group,

6 3 6 2 6

Halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

-Luoxy group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi group

1 6 1 6

Group, (C—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (

1 6 1 6

C—C) alkthio group, halo (C—C) alkthio group, (C—C) alkyl group

2 6 2 6 2 6

Rusulfyl group, halo (C—C) alkulsulfyl group, (C—C) alkell

2 6 2 6

Sulfol group, halo (C—C) alkaryl sulfonyl group, mono (C—C) alkylamino Group, di (c C) alkylamino group, (C—C) alkylsulfide, which may be the same or different

1 6 1 6

Holamino group, halo (c -c) alkylsulfonylamino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkyl carbo group, (C C) alkyloxy carbo-

1 6 1 6

Group, phenol group, halogen atom which may be the same or different, cyan group, nitro group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (C C

6 1 6 1 6 1

) Alkoxy group, (c -C) alkylthio group, halo (c -c) alkylthio group, (C

6 1 6 1 6 1

C) alkylsulfinyl group, halo (C—C) alkylsulfinyl group, (C—C) al

6 1 6 1 6 One or more selected from a killylsulfonyl group or a halo (C—C) alkylsulfonyl group

1 6

A substituted phenyl group having a substituent, a phenoxy group, or a halogen atom, cyan group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, which may be the same or different, (C

1 6 1 6

— C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group, halo

1 6 1 6 1 6

(C —C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) al

1 6 1 6 1 6 Killsulfier group, (C—C) alkylsulfonyl group or halo (C—C) alkyls

1 6 1 6

A substituted phenyl group having one or more substituents selected, a substituted phenyl group having one or more substituents selected, an aromatic 6-membered bicyclic group having 1 to 2 nitrogen atoms, or the same or Different halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (CC) alkyl group, (CC) alkoxy group, halo (CC) a

6 1 6 1 6 1 6 Lucoxy group, (C—C) alkenyloxy group, halo (c -c) alkoxy group, (C

2 6 2 6

— C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfi group

1 6 1 6 1 6

Nyl group, halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (

1 6 2 6

C—C) alkenyl dithio group, (C—C) alkenylsulfinyl group, halo (C—C) a

2 6 2 6 2 6 Lucenylsulfinyl group, (C C) alkylsulfonyl group, halo (C C) alkyl

1 6 1 6 sulfonyl group, (c—C) alkenylsulfonyl group, halo (C—C) alkenylsulfo group

2 6 2 6 Nyl, mono (C—C) alkylamino or di (C—C) which may be the same or different

1 6 1 6

Ar ² is a phenyl group, a halogen atom which may be the same or different, a nitro group, a cyano group, a (C —C) alkyl group, a halo (C—C) alkyl group, a (C—C) alkoxy group, a halo (C

1 6 1 6 1 6 1 C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C—C)

6 2 6 2 6 2 6 Alkyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group, halo (C

3 6 2 6

—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) alkylthio group

2 6 1 6 1 6

Group, (C—C) alkylsulfonyloxy group, halo (C—C) alkylsulfonyl group

1 6 1 6

A xyl group, a (C—C) alkylsulfinyl group, a halo (C—C) alkylsulfiel group,

1 6 1 6

(C—C) alkynolesulfonyl group, halo (C—C) alkynolesulfonyl group, (C—C)

1 6 1 6 2 6 Alkenylthio group, halo (C—C) alkenylthio group, (C—C) alkenylsulfide

2 6 2 6

Nyl group, halo (C—C) alkenylsulfinyl group, (C—C) alkenylsulfonyl

2 6 2 6

Group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino group, identical

2 6 1 6

Or a di (C—C) alkylamino group which may be different, (C—C) alkylsulfonyl

1 6 1 6

Mino group, halo (C—C) alkylsulfonylamino group, (C—C) alkylcarbonyl group

1 6 1 6

Halo (C 1 C) alkylcarbonyl group, (C 1 C) alkyloxycarbonyl group,

1 6 1 6

Phenyl group, halogen atom which may be the same or different, cyan group, nitro group, (C—C

1 6) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkyl group

1 6 1 6

1 6

1 6 1 6 1 6

) Alkoxy, halo (C—C) alkoxy, (C—C) alkylthio, halo (C 1

1 6 1 6 1

C) alkylthio, (C—C) alkylsulfier, halo (C—C) alkyls

6 1 6 1 6

Rufyl group, (C—C) alkyl sulfo group or halo (C—C) alkyl sulfo group

A substituted phenyl group having one or more substituents selected from a substituted phenoxy group having one or more substituents selected from 1 6 1 6 group, an aromatic 6-membered heterocyclic group having 1 to 2 nitrogen atoms Or the same or different, halogen atom, cyan group, nitro group, (C—C)

16 alkyl, halo (C—C) alkyl, (C—C) alkoxy, halo (C—C) alkyl

2 6 2 6 1

C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfini

6 1 6 1 6 Group, halo (c -c) alkylsulfier group, (C—C) alkenylthio group, halo (C

1 6 2 6

— C) alkenylthio group, (C—C) alkenylsulfier group, halo (C—C) al

2 6 2 6 2 6 Kenylsulfuryl group, (C—C) alkylsulfol group, halo (C—C) alkyls

1 6 1 6

Ruphorol group, (C—C) alkenylsulfol group, halo (C—C) alkylsulfol group

2 6 2 6

1 6 1 6 Alkylamino group power A substituted aromatic 6-membered heterocyclic group having 1 or 2 nitrogen atoms having one or more selected substituents.

1 6 1 6 group, (C C) alkyl group, halo (C C) alkenyl group, (C C) alkyl group

2 6 2 6 2 6

, Halo (C—C) alkyl group, (C—C) alkylthio group, halo (CI—C6) alkyl

2 6 1 6

Thio group, (C—C) alkyl carbo group, halo (C—C) alkyl carbo group, (

1 6 1 6

C—C) alkoxycarbonyl group or halo (C—C) alkoxycarbonyl group.

1 6 1 6

), A sulfur atom or a single bond.

R is a hydrogen atom, (C C) alkyl group, halo (C C) alkyl group, (C C) cyclo

3 6 2 10 2

C) alkyl group, (C—C) alkyl group, halo (C—C) alkyl group, (C

10 2 10 2 10 1

C) alkoxycarbol (C—C) alkyl group, phenol (C—C) alkyl group or

6 1 6 1 6

1 6 1 6 1 6

, (C—C) alkenyloxy, halo (C—C) alkenyloxy, (C—C)

1 6 1 6

Halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C

1 6 2 6 2 6

) Alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyl group

1 6 1 6

Nyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group

2 6 2 6

A mono (C—C) alkylamino group or the same or different di (C—C) al

1 6 represents an alkyl group. R ² represents a hydrogen atom, a (C—C) alkyl group, a halo (C—C) alkyl group, a cyano (C—C

1 6 1 6 1 6

) Alkyl group, (C—C) alkyl group, halo (C—C) alkenyl group, (C—C)

2 10 2 10 2 10 Alkyl group, halo (C—C) alkynyl group, (C—C) alkoxycarbol (C

2 10 1 6 1

—C) alkyl group, phenyl (C—C) alkyl group, halogen which may be the same or different

6 1 6

Atom, cyano group, nitro group, (C 1 -C 6) alkyl group, halo (C 1 C) alkyl group, (C

1 6 1 6 1

-C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkoxyloxy group,

6 1 6 2 6

Halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C—C) al

2 6 1 6 1 6 Kirthio group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi-

1 6 1 6

Group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C)

2 6 2 6 2 6 Lucenyl sulfier group, halo (C—C) alkenyl sulfier group, (C—C) al

2 6 1 6 Killsulfonyl group, halo (C—C) alkylsulfonyl group, (C—C) alkenylsulfonyl group

1 6 2 6

Phonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino group

1 6

Substituted phenyl (C 1 C) alkyl groups having 1 substituent on the ring, nitrogen atoms 1 to 2

1 6

Aromatic 6-membered heterocyclic (C 1 C) alkyl group or same or different

1 6

1 6 1 6 2 6

Si group, halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C

2 6 1 6 1 6

) Alkylthio, (C—C) alkylsulfinyl, halo (C—C) alkylsulf

1 6 1 6

Finyl group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C 1

2 6 2 6 2

C) alkeninoresulphinyl group, halo (C—C) alkenylsulfinyl group, (C—C)

1 6 2 6

Sulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino

2 6 1 6

Group or di (c-c) alkylamino groups which may be the same or different

1 6

A substituted aromatic 6-membered heterocyclic (C 1 C) alkyl group having 1 to 2 nitrogen atoms having the above substituent on the ring is shown.

6

R ³ , R ⁴ , R ⁷ and R ⁸ may be the same or different, a hydrogen atom, a (C—C) alkyl group,

1 6

A halo (C—C) alkyl group, a (C—C) cycloalkyl group or a halo (C—C) cycloa

1 6 3 6 3 6 Represents an alkyl group, and R ³ and R ⁴ are joined together to form a C alkylene group.

1—C) Al

6

it can.

2

Child, (c -c) alkyl group, halo (c -c) alkyl group, (c -c) alkylcarbohydrate

1 6 1 6 1 6

Halo group, halo (c 1 -c) alkylcarbonyl group, (

6 c 1 -c) alkoxy (

6 c 1 -c)

6 group or a (C C) alkoxycarbonyl group. N is 0 or an integer from 1 to 4

1 6

Indicates a number. } Acetonitrile derivative represented by:

Furthermore, the present invention relates to a pest control agent, particularly an agricultural and horticultural insecticide and animal parasite control agent, characterized by containing the compound as an active ingredient, and a method of using them.

The invention's effect

[0009] The acetonitrile derivative of the present invention exhibits a remarkable pest control activity even at a low dose, and is useful as an agricultural or horticultural insecticide or animal parasite control agent.

BEST MODE FOR CARRYING OUT THE INVENTION

In the definition of the acetonitrile derivative represented by the general formula (I) of the present invention, “halogen atom” means a chlorine atom, bromine atom, iodine atom or fluorine atom, and “(c group)”

1 C) Alky

6

Is, for example, linear or branched such as methyl group, ethyl group, n propyl group, i propyl group, n butyl group, i butyl group, s butyl group, t butyl group, n-pentyl group, n-hexyl group, etc. Represents a chain-like alkyl group of 1 to 6 carbon atoms and represents “halo (C

1 C) Al

“6 groups” means a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, and “(C alkyl group”).

3C) Cycloa

6

Is a cyclic alkyl group having 3 to 6 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and may be interrupted by an oxygen atom, a sulfur atom, or a nitrogen atom. Specific examples of `` 8-membered ring '' include pyrrolidine ring, pyrrole ring, pyrrolidine ring, pyrazoline ring, pyrazole ring, imidazolidine ring, imidazoline ring, imidazole ring, triazoline ring, triazole ring, tetrazole ring, thiazoline ring, oxazoline ring , Isoxazoline ring, isothiazoline ring, piperazine ring, piperidine ring, monoreforin ring, thiomorpholine ring, oxazine ring, thiazine ring, etc., and `` has 1 or 2 nitrogen atoms Specific examples of the “aromatic 6-membered heterocyclic group” include a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyradyl group, and the like.

Among the acetonitrile derivatives represented by the general formula (I) of the present invention, particularly preferred are compounds represented by the general formula (I 1), (I 2) or (I 3), which are suitable for the following: Examples of substituents are shown below.

Q ¹ is preferably the same or different halogen atom, (C—C) alkyl

1 6

Group, halo (C—C) alkyl group, (C—C) alkyloxy group or halo (C—C) alkyl

1 6 1 6 1 6 A substituted phenyl group having a alkoxy group as a substituent, or a halo (C C) alkyl group which may be the same or different, or a substituted phenyl having a halogen atom on the ring as a substituent (C

1 6 1

—C) an alkyl group, specifically, a 2-chlorophenyl group, a 3-methylphenol group,

6

4 Chloroform group, 2, 3 dichlorophenol group, 2, 4 dichlorophenol group, 4 bromophenol group, 4 trifluoromethylphenol group, 4 trifluoromethoxyphenol group 4 chlorobenzyl group, 4 trifluoromethylbenzyl group, and the like.

Q ² is preferably a phenyl group or a substituted phenyl group, particularly preferably a halo (CC) alkyl group or a halogen atom which may be the same or different, as a substituent.

1 6

A substituted phenol group. Specific examples include 2-clonal ring groups, 3-clonal ring groups, 4-clonal ring groups, 2,3-dichlorophenol groups, 2,4-dichlorophenol groups, and 4-bromophenol groups. Group, 3-trifluoromethylphenol group, 4-trifluoromethylphenol group and the like.

Ar ¹ is preferably a halo (C—C) alkyl group or a halogen atom as a substituent.

1 6

Specific examples of the substituted phenyl group include, but are not limited to, a 2-chlorophage group, a 3-chlorophage group, a 4-chlorophage group, a 2,3-dichlorophenol group, and a 2,4-dichlorophenol. -L group, 4-bromophenyl group, 4-trifluoromethylphenol group and the like.

Ar ² is preferably a phenyl group or a substituted phenyl group, and particularly preferably a halo (C—C) alkyl group or a substituted phenyl group having a halogen atom as a substituent.

1 6

Specifically, 2-chloro-phenol group, 3-chloro-phenol group, 4-chloro-phenol group, 2,3-dicyclo-phenol group, 2,4-dichloro-phenol group, 4-bromo phenol -L group, 4-trifluoromethylphenol group and the like. G is preferably NH or a single bond.

R is preferably a (C—C) alkyl group.

1 6

R ¹ is preferably a hydrogen atom or a (C 1 -C 6) alkyl group, particularly preferably water.

1 6

It is an elementary atom.

R ² is preferably a hydrogen atom, a (C—C) alkyl group, or a cyano (C—C) alkyl group.

1 6 1 6

, (C—C) alkyl group, (C—C) alkyl group, (C—C) alkoxycarbo group

2 6 2 6 1 6

Ru (C—C) alkyl group, fur (C—C) alkyl group, substituted fur (C—C)

1 6 1 6 1 6 An alkyl group, a pyridyl (C—C) alkyl group or a substituted pyridyl (C—C) alkyl group.

1 6 1 6

The (C—C) alkyl group, cyano (C—C) alkyl, phenol (C—C) alkyl group

1 6 1 6 1 6

And the substituted carbon (C C) alkyl group preferably has 1 to 3 carbon atoms in the alkyl group.

1 6

Good. Preferred substituents for substituted phenol (C—C) alkyl groups include (C—C)

1 6 1 6 alkyl group or halogen atom, for example, 2 chlorobenzene, 3 benzene, 4 benzene, 2, 3 dichlorobenzene, 2, 4 dichlorobenzene Examples thereof include a benzyl group, a 2- (4-chlorophenyl) ethyl group, a 2-methylbenzyl group, a 3-ethylbenzyl group, and a mono (4-methylphenyl) ethyl group.

R ³ , R ⁴ , R ⁷ and R ⁸ are preferably hydrogen atoms.

R ⁵ is preferably a (C—C) alkyl group, (C—C) alkoxy (C—C) alkyl.

1 6 1 6 1 6 group, a substituted phenoxy (C—C) alkyl group.

1 6

R ⁶ is preferably a hydrogen atom or a (C—C 6) alkyl group. R ⁶ and R together

1 6

Among these, it is particularly preferable to form a ring, and a 5-membered ring or a 6-membered ring is particularly preferable.

W is preferably NR ⁹ — which forms a 5- to 8-membered ring which may be interrupted by an oxygen atom, sulfur atom or nitrogen atom together with an oxygen atom or R ^5, and is preferred as the 5- to 8-membered ring. Is a pyrrole ring, pyrazoline ring, pyrazole ring, imidazole ring, triazole ring, tetrazole ring, piperazine ring, piperidine ring, morpholine ring or thiomorpholine ring, particularly preferably a piperazine ring, piperidine ring, A morpholine ring or a thiomorpholine ring. n is preferably 0 or 1, particularly preferably 0.

The substituted aromatic 6-membered heterocyclic group having 1 or 2 nitrogen atoms is preferably a pyridyl group. [0012] The acetonitrile derivative represented by the general formula (I) of the present invention includes two or more optical isomers and diastereomers derived from one or more asymmetric centers in the structural formula. In some cases, the present invention encompasses all mixtures containing each optical isomer and diastereomer in any proportion. The acetonitrile derivative represented by the general formula (I) of the present invention may have a geometric isomer derived from a carbon-carbon double bond or a carbon-nitrogen double bond in its structural formula. The invention encompasses all geometric isomers and mixtures containing them in any proportion. Further, the present invention encompasses all tautomers that can be considered as the general formula (I).

The typical production methods of the present invention are schematically shown below, but the present invention is not limited to these.

[0013] Manufacturing method 1

(VI) (La) (1-1)

(Where

R ³ , R ⁴ and R ⁵ are the same as above, hal represents a halogen atom, and M represents a metal atom such as a sodium atom or a potassium atom. )

A haloketone represented by the general formula (II) and a compound represented by the general formula (III) are reacted in the presence of a base in the presence or absence of an inert solvent and represented by the general formula (IV). The ketones are isolated from or represented by the general formula (V) in the presence or absence of an ammonium salt and in the presence or absence of an inert solvent. Reaction with a metal cyanide to form an amino-tolyl compound represented by the general formula (VI), and the amino-tolyl compound is isolated or not isolated in the presence of a base, in the presence of an inert solvent or inactive. Reacting with an acid halide represented by the general formula (VII) in the presence to produce the compound of the present invention represented by the general formula (Ila) Can do. Further, the compound represented by the general formula (I 1) is reacted with a compound or a compound represented by the general formula (VIII) in the presence of a base, in the presence or absence of an inert solvent. Invention compounds can be produced.

1-1. General formula (Π) → —General formula (IV)

Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride and sodium hydride, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, Examples thereof include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, organic bases such as pyridine and triethylamine, and two or more kinds of bases can also be used. The amount of the base used may be appropriately selected within the range of 0.8 mole to 2 moles relative to the haloketones represented by the general formula (II). The solvent that can be used in this reaction is not particularly limited as long as it does not inhibit this reaction. , Esters such as methyl acetate and ethyl acetate, ethers such as ethyl ether, tetrahydrofuran and dioxane, ketones such as acetone and methyl ethyl ketone, acetonitrile, Ν, ジメチル dimethylformamide, Ν-methylpyrrolidone, dimethyl sulfoxide, water, Examples thereof include polar solvents such as pyridine, and these may be used as a mixture of two or more.

Since this reaction is an equimolar reaction, the haloketones represented by the general formula (Π) and the compound represented by the general formula (III) may be reacted in an equimolar amount. You can also.

The reaction temperature may be appropriately selected from the range of 0 ° C to the boiling point of the reaction solvent. The reaction time is not constant depending on the reaction scale and reaction temperature, but may be appropriately selected within the range of 1 to 48 hours.

After the reaction, the target ketone represented by the general formula (IV) can be isolated by a conventional method. For example, when a solvent that dissolves in water is used, the solvent is distilled off under reduced pressure, After adding water, extract with a poorly water-soluble solvent such as benzene, toluene and xylene, aromatic hydrocarbons such as chloroform and dichloromethane, esters such as ethyl acetate, and saturated saline. After washing with anhydrous sodium sulfate, anhydrous magnesium sulfate, etc. What is necessary is just to dry with a desiccant and to distill off a solvent under reduced pressure. The residue obtained after distilling off the solvent can be purified by recrystallization, suspension washing, column chromatography or the like, if necessary. It can also be used in the next reaction without isolation.

1-2. General formula (IV) → —General formula (VI)

Examples of the metal cyanide that can be used in this reaction include the ability to use alkali metal cyanide such as sodium cyanide and potassium cyanide. As the cyan source, trimethylsilyl cyanide, acetone cyanohydrin, etc. Other organic cyanides can also be used. The amount of cyanide used is a force that can be used in the range of 0.5 to 10 times the moles of the ketone represented by the general formula (IV), preferably in the range of equimolar to 3 times the mole. It is. As the ammonium salt, ammonia salts such as ammonium chloride, ammonium sulfate, ammonium formate, and ammonium acetate can be used. The force that can be used in the range of 0.5 to 10 moles relative to the genus cyanide is preferably in the range of equimolar to 5 moles.

The solvent that can be used in this reaction is not particularly limited as long as it does not inhibit this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, alcohols such as methanol, ethanol, isopropyl alcohol, Halogenated hydrocarbons such as chlorohonolem and dichloromethane, esters such as methyl acetate and ethyl acetate, ethers such as jetyl ether, tetrahydrofuran and dioxane, acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide And polar solvents such as water and pyridine.

After the reaction, the desired amino-tolyl represented by the general formula (VI) can be isolated by the same conventional method as 1-1. It can also be used in the next reaction without isolation. This reaction is a method known as a Strecker reaction, and conforms to known literature (eg, Formation of C—C Bonds, Vol. 1, Georg Thieme Publishers, 1973, Organic Synthesis, Coll. Vol. 3, 88, etc.) The reaction operation may be performed. 1-3. General formula (VI) → —General formula (I la)

This reaction may be carried out according to 1 1.

1 -4. General formula (I la) → —General formula (I)

This reaction may be carried out according to 1 1.

[0016] Manufacturing method 2

(Ι Ι '(IV)

(VI) (Ha) (I)

(In the formula, QW, R, R \ R ³ , R ⁴ , R ⁵ and hal are the same as above.)

In the presence of a base, a ketone represented by the general formula (II ′) and a halide represented by the general formula (VIII ′) are reacted in the presence or absence of an inert solvent to react with the general formula (IV In the same manner as in Production Method 1, the compound of the present invention represented by general formula (Ila) or general formula (I) can be produced.

2- 1. General formula (Π ') → —General formula (IV)

This reaction may be carried out according to 1 1.

[0017] Manufacturing method 3.

(XI I) (I-2a)

(1-2)

(Where

R ⁶ and hal are the same as described above, and L represents a leaving group such as a halogen atom, a methanesulfur group, a p-toluenesulfol group, or a p-bromobenzenesulfol group. )

Amines represented by the general formula (IX) and acid halides represented by the general formula (VII) are reacted in the presence of a base in the presence or absence of an inert solvent to give a general formula (X) Then, the amides may be isolated or reacted with the halides represented by the general formula (VIII) in the presence or absence of an inert solvent. An amide represented by the general formula (XII) is isolated or is not isolated and is represented by the general formula (XI) in the presence of a base, in the presence or absence of an inert solvent. To the thioamide represented by the general formula (I 2a), which is a compound of the present invention, and is isolated or not isolated in the presence of a base. The compound of the present invention represented by the general formula (I 2) is produced by reacting with a halide represented by the general formula (XIII) in the presence or absence of an inert solvent. The It can be done.

When R ¹ is a hydrogen atom, it is represented by the general formula (X) in the presence or absence of an inert solvent through the amide represented by the general formula (XII). The thiamides which are the compounds of the present invention represented by the general formula (I 2a) can be produced by reacting the amides represented by the general formula (XI) with the isothiocyanates represented by the general formula (XI).

[0019] 3- 1. General formula (IX) → General formula (X)

Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride and sodium hydride, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, Examples thereof include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, organic bases such as pyridine and triethylamine, and two or more kinds of bases can also be used. The amount of the base used may be appropriately selected within the range of 0.8 mole to 2 moles relative to the amine represented by the general formula (IX).

The solvent that can be used in this reaction is not particularly limited as long as it does not inhibit this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as chloroform, dichloromethane, and the like. , Esters such as methyl acetate and ethyl acetate, ethers such as ethyl ether, tetrahydrofuran and dioxane, polar solvents such as acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, water and pyridine These can be used as a mixture of two or more. Since this reaction is an equimolar reaction, the amine represented by the general formula (IX) may be reacted with the acid halide represented by the general formula (VII) in an equimolar amount. Use the amount.

[0020] The reaction temperature may be appropriately selected within the range of room temperature to the boiling point of the reaction solvent. Although the reaction time is not constant depending on the reaction scale and reaction temperature, it may be appropriately selected within the range of 1 to 48 hours.

After the reaction, in order to isolate the target amide represented by the general formula (X), when a solvent that dissolves in water is used, the solvent is distilled off under reduced pressure and water is added. Extracted with aromatic hydrocarbons such as benzene, toluene and xylene insoluble in water, halogenated hydrocarbons such as chloroform and dichloromethane, esters such as ethyl acetate, etc., washed with saturated saline, It may be dried with a desiccant such as anhydrous sodium sulfate or anhydrous magnesium sulfate, and the solvent may be distilled off under reduced pressure. The residue obtained after distilling off the solvent can be purified by recrystallization, suspension washing, column chromatography or the like, if necessary. It can also be used in the next reaction without isolation.

[0021] 3- 2. General formula (X) → —General formula (ΧΠ)

This reaction can be performed according to 3-1.

3- 3. General formula (X) or General formula (XII) → General formula (I 2a)

As the base that can be used in this reaction, strong bases are preferred, for example, alkali metal hydrides such as lithium hydride and sodium hydride, metal amides such as sodium amide, lithium diisopropylamide and lithium hexamethyldisilazide, Examples include alkyl metals such as n-butyllithium, sec butyllithium, and tertbutyllithium, and alkoxides such as tertbutoxysodium and tert-butoxypotassium. Two or more bases can also be used. it can. The amount of the base used may be appropriately selected within the range of 0.8 mole to 2 moles relative to the amide represented by the general formula (XII). In addition, when R ¹ is a hydrogen atom, the amount of base to be used may be appropriately selected within the range of 1.8 times to 4 times the amount of the amide represented by the general formula (X). .

The solvent that can be used in this reaction is not particularly limited as long as it does not inhibit this reaction. Examples thereof include aromatic hydrocarbons such as benzene, toluene, and xylene, ethers such as jetyl ether, tetrahydrofuran, and dioxane. Can be mentioned.

[0022] Since this reaction is an equimolar reaction, the amide represented by the general formula (X) or (XII) and the general formula

The isothiocyanate represented by (XI) may be reacted in an equimolar amount, but either one can be used in excess.

The reaction temperature may be appropriately selected from the range of 100 ° C to the boiling point of the reaction solvent, but is preferably in the range of -78 ° C to room temperature. The reaction time is not constant depending on the reaction scale and reaction temperature, but may be appropriately selected within the range of 1 to 48 hours. After the reaction, the amides represented by the general formula (I-2a), which is the target product, can be isolated in the same manner as in 3-1, but can also be used in the next reaction without isolation. it can.

Isothiocyanates represented by the general formula (XI) are known literatures (for example, Organic Synth esis, Coll. Vol. 1, 844, Organic Synthesis, Coll. Vol. 2, 323, etc.) and can also be purchased as a commercial product.

3-4. General formula (I 2a) → —General formula (I 2)

This reaction can be performed according to 3-1.

[0023] Manufacturing method 4.

(XI I-1) (I-2b)

(I-2c)

(Where

X ¹ , X ² , hal and L are the same as above. )

[0024] The amine represented by the general formula (IX-1) and the acid halide represented by the general formula (VII) are reacted in the presence or absence of an inert solvent in the presence of a base group. In the presence or absence of a base, in the presence or absence of an inert solvent, the amides represented by the general formula (X-1) are not isolated or isolated. It reacts with the halide represented by (VIII) to give an amide represented by the general formula (XII-1), and the amide is not isolated or isolated, and in the presence of a base, an inert solvent is used. In the presence or absence of isotope represented by general formula (XI) By reacting with cyanates, thioamides represented by the general formula (I 2b), which are the compounds of the present invention, can be produced. Furthermore, the thiamides represented by the general formula (I 2b) are isolated or not reacted with the compound represented by the general formula (XIV) in the presence of a base, in the presence or absence of an inert solvent. Thus, the compound of the present invention represented by the general formula (I 2c) can be produced.

In addition, when R ¹ is a hydrogen atom, the compound represented by the general formula (X—) can be used in the presence of a base, in the presence or absence of an inert solvent without passing through the amide represented by the general formula (ΧΠ—1). The amide represented by the general formula (I-2b) as the compound of the present invention is produced by reacting the amide represented by 1) with the isothiocyanate represented by the general formula (XI). be able to.

[0025] 4- 1. General formula (IX— 1) → General formula (X— 1)

This reaction can be performed according to 3-1.

4- 2. General formula (X-1) → General formula (XII-1)

This reaction may be performed according to 3-2.

4- 3. General formula (X-1) or (XII-1) → General formula (I 2b)

This reaction can be performed according to 3-3!

4-4. General formula (I 2b) → —General formula (I 2c)

This reaction may be carried out according to 3-4.

[0026] Manufacturing method 5.

MCN Ammonium salt

(V)

Ar! NCS Ar'NCO

(XI-1) (XI-2)

(XVII)

'_L base

(XVIII)

R 'ial -Ar ²

(I-3b) (I-3c) (where ΑΛ Ar ² , R, R ³ , R ⁴ , R ⁷ , R ⁸ , W, M, L, n and hal are the same as above, R ² , Is a (C—C 1) alkyl group, a halo (C 1 -C 4) alkyl group, a cyano (C 1 -C 4) alkyl group,

1 6 1 6 1 6

C -C) alkenyl group, halo (C -C) alkenyl group, (c -c) alkynyl group,

2 10 2 10 2 10

Halo (c -c) alkynyl group, (c -c) alkoxycarbol (C—C) alkyl

2 10 1 6 1 6

Group, phenyl (C—C) alkyl group, halogen atom, cyan group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, which may be the same or different, (C 1 C ) Alkoki

1 6 1 6 1 6 Si group, halo (c—C) alkoxy group, (C—C) alkoxy group, halo (C—C) a

1 6 1 6 1

—C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C)

6 1 6 2 6 alkarylthio group, halo (C—C) alkarylthio group, (C—C) alkulsulfyl group

2 6 2 6

-Luyl group, halo (C—C) alkylsulfyl group, (C—C) alkylsulfol group

2 6 1 6

, Halo (C—C) alkyl sulfonyl group, (C—C) alkyl sulfonyl group, halo (C

1 6 2 6

— C) alkylsulfol group, mono (C—C) alkylamino group or the same or

2 6 1 6

1 6

Substituted phenyl (C C) alkyl group, aromatic having 1 or 2 nitrogen atoms 6

1 6

A membered heterocyclic (C C) alkyl group or a halogen atom which may be the same or different;

1 6

Ano group, nitro group, (C C) alkyl group, halo (C C) alkyl group, (C C) al

1 6 1 6 1 6 Coxi group, halo (C—C) alkoxy group, (C—C) alkenyloxy group, halo (C—C

1 6 2 6 2

) Alkenyloxy group, (c—C) alkylthio group, halo (C—C) alkylthio group,

6 1 6 1 6

(C—C) alkylsulfinyl group, halo (C—C) alkylsulfinyl group, (C—C

1 6 1 6 2

) Alkenylthio, halo (c—C) alkenylthio, (C—C) alkenylsulfur

6 2 6 2 6

Ynyl group, halo (C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl

2 6 1 6

Group, halo (C—C) alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo

1 6 2 6

(C—C) alkenylsulfonyl group, mono (C—C) alkylamino group or the same

2 6 1 6

The di (C—C) alkylamino group, which may be different, is also selected.

1 6

Substituted aromatic 6-membered heterocyclic (C C) alkyl having 1 or 2 nitrogen atoms above

1 represents 6 groups. )

A ketone represented by the general formula (XV) is reacted with a metal cyanide represented by the general formula (V) in the presence of an ammonia salt, in the presence or absence of an inert solvent. After the aminoacetonitriles represented by (XVI), the aminoacetonitriles are isolated or not isolated and represented by the general formula (XI-1) in the presence or absence of an inert solvent. The thiourea represented by the general formula (I 3a), which is the compound of the present invention, can be produced by reacting with the isothiocyanate. Subsequently, the thioureas are isolated or unisolated and reacted with the compound represented by the general formula (xvm) in the presence of a base, in the presence or absence of an inert solvent. The isothiourea represented by the general formula (I 3b), which is the compound of the present invention, is isolated, and the isothiourea is isolated or not isolated, in the presence of a base, in the presence or absence of an inert solvent. The compound of the present invention represented by the general formula (I 3c) can be produced by reacting with a halide represented by the general formula (VIII) below.

The thiourea represented by the general formula (I-3a) is represented by the aminoacetonitrile represented by the general formula (XVI) and the general formula (XI-2) in the presence or absence of an inert solvent. To the ureas represented by the general formula (XVII), and the ureas are isolated with or without isolation in the presence or absence of a base. It can be produced by reacting with a Lawson reagent in the presence or absence.

[0029] 5- 1. General formula (XV) → General formula (XVI)

Examples of the metal cyanide that can be used in this reaction include the ability to use alkali metal cyanide such as sodium cyanide and potassium cyanide. As the cyan source, trimethylsilyl cyanide, acetone cyanohydrin, etc. Other organic cyanides can also be used. The amount of the cyanide used is a force that can be used in the range of 0.5 to 10 times moles relative to the ketones represented by the general formula (XV), preferably in the range of equimolar to 3 times moles. The As the ammonium salt, ammonium salts such as ammonium chloride, ammonium sulfate, ammonium formate, and ammonium acetate can be used. Power that can be used in the range of 0.5 to 10 times the mole of cyanide, preferably in the range of equimolar to 5 times the mole.

The solvent that can be used in this reaction is not particularly limited as long as it does not inhibit this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, alcohols such as methanol, ethanol, and isopropyl alcohol, Halogenated hydrocarbons such as chlorophorem and dichloromethane, esters such as methyl acetate and ethyl acetate, ethers such as jetyl ether, tetrahydrofuran and dioxane, acetonitrile, N, N dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, Examples thereof include polar solvents such as water and pyridine.

[0030] The reaction temperature may be appropriately selected within the range of room temperature to the boiling point of the reaction solvent. The reaction time is not constant depending on the reaction scale and reaction temperature, but is appropriately selected within the range of 1 to 48 hours. Just do it.

After the reaction, in order to isolate the target aminoacetonitrile represented by the general formula (XVI), if a solvent that dissolves in water is used, the solvent is distilled off under reduced pressure and water is added. Extracted with aromatic hydrocarbons such as benzene, toluene and xylene insoluble in water, halogenated hydrocarbons such as chloroform and dichloromethane, esters such as ethyl acetate, etc., washed with saturated saline, What is necessary is just to dry with desiccants, such as anhydrous sodium sulfate and anhydrous magnesium sulfate, and to distill off a solvent under pressure reduction. The residue obtained after distilling off the solvent can be purified by recrystallization, suspension washing, column chromatography or the like, if necessary. It can also be used in the next reaction without isolation.

This reaction is a method known as a Strecker reaction, and conforms to known literature (eg, Formation of C—C Bonds, Vol. 1, Georg Thieme Publishers, 1973, Organic Synthesis, Coll. Vol. 3, 88, etc.) The reaction operation may be performed. In addition, the ketones represented by the general formula (XV) can be produced according to a known method, for example, a production method disclosed in JP-A-2000-26392.

5-2. General formula (XVI) → —General formula (I 3a)

Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride and sodium hydride, alkali metal hydrides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, Examples thereof include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, and organic bases such as pyridine and triethylamine. What is necessary is just to select the usage-amount of a base suitably in the range of 0.8 times-2 times mole with respect to aminoacetonitrile represented by general formula (XVI). It is also possible to carry out the reaction without using a base.

The solvent that can be used in this reaction is not particularly limited as long as it does not inhibit this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, alcohols such as methanol, ethanol, and isopropyl alcohol, Ketones such as acetone and methyl ethyl ketone, halogenated hydrocarbons such as chloroform and dichloromethane, esters such as methyl acetate and ethyl acetate, ethers such as jetyl ether, tetrahydrofuran and dioxane, and acetonitrile , N, N dimethylformamide, N-methylpyrrolidone, dimethyls Examples thereof include polar solvents such as sulfoxide, water, and pyridine.

[0032] Since this reaction is an equimolar reaction, if an aminoacetonitrile represented by the general formula (XVI) and an isothiocyanate represented by the general formula (XI-1) are reacted in an equimolar amount, Good, but either can be used in excess.

The reaction temperature may be appropriately selected within the range of room temperature to the boiling point of the reaction solvent. Although the reaction time is not constant depending on the reaction scale and reaction temperature, it may be appropriately selected within the range of 1 to 48 hours. After the reaction, the aminoacetonitrile represented by the general formula (XVI), which is the target product, can be isolated in the same manner as in 5-1, but it can also be used in the next reaction without isolation. Isothiocyanates represented by general formula (XI-1) can be produced according to known literature (eg, Organic Synthesis, Coll. Vol. 1, 844, Organic Synthesis, Coll. Vol. 2, 323, etc.). Also, it can be purchased as a commercial product.

[0033] 5- 3. General formula (I 3a) → General formula (I 3b)

Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride and sodium hydride, alkali metal hydrides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, Examples thereof include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, and organic bases such as pyridine and triethylamine. The amount of the base used may be appropriately selected within the range of 0.8 to 2 moles compared to the thioreas represented by the general formula (I 3a), but it is preferable to use an excess amount.

Since this reaction is an equimolar reaction, the thiourea represented by the general formula (I 3a) and the compound represented by the general formula (XVIII) may be reacted in an equimolar amount, but either one is used in excess. You can also. The solvent, reaction temperature, reaction time, and isolation method that can be used in this reaction are the same as 5-2.

[0034] 5-4. General formula (I 3b) → —General formula (I 3c)

This reaction should be the same as 5-3.

5- 5. General formula (XVI) → General formula (XVII)

This reaction should be the same as 5-2.

5-6. General formula (XVII) → —General formula (I 3a)

This reaction is a method described in known literature (for example, Tetrahedoron, No. 41, 5061 (1985)). According to

Manufacturing method 6.

Ar ^ Ohal

a- (XVI I I)

3d) (I-3e)

(Where ΑΛ Ar ² , R, R ² ′, R ³ , R ⁴ , R ⁷ , R ⁸ , W, L, hal and n are the same as above.)

[0036] An aminoacetonitrile represented by the general formula (XVI) and an acid halide represented by the general formula (XIX) are reacted in the presence of a base in the presence or absence of an inert solvent. An amide represented by the formula (XX) is isolated or not isolated and reacted with a Lawson reagent in the presence or absence of a base, in the presence or absence of an inert solvent. A thioamide that is a compound of the present invention represented by the general formula (I 3d) is used, and the thioamide is not isolated or isolated, but in the presence of a base and in the presence or absence of an inert solvent. The compound of the present invention represented by the general formula (I 3e) can be produced by reacting with a compound represented by XVIII).

6- 1. General formula (XVI) → —General formula (XX)

This reaction may be performed according to 5-2.

6- 2. General formula (XX) → —General formula (I 3d)

This reaction may be carried out according to production method 5-5.

6- 3. General formula (I 3d) → —General formula (I 3e)

This reaction can be performed according to 5-3!

[0037] Production method 7. Production method when G is a sulfur atom

(I-3f) (I-3g)

(Where ΑΛ Ar ² , R, R ² ′, R ³ , R ⁴ , R ⁷ , R ⁸ , M, W, L, hal and n are the same as above.) [0038] In general formula (XVI) In the presence of a base, the aminoacetonitrile represented is reacted with a disulfuric acid carbon represented by the formula (XXI) to form a dithiolate and reacted with a compound represented by the general formula (XVIII) without isolation. The compound represented by the general formula (XXII) is isolated, or is isolated and reacted with the mercabtan metal salt represented by the general formula (XXIII) to represent the compound represented by the general formula (I 3g). The compound of the present invention can be produced. In addition, when an arylolide represented by the general formula (XXIV) having high reactivity is used, dithiolate is reacted with the aminoacetonitrile represented by the general formula (XVI) in the presence of a base. The compound of the present invention represented by the general formula (I 3g) can be produced via the dithiocarbamate represented by the general formula (I 3f) or a salt thereof by introducing substituents step by step. it can.

[0039] 7- 1. General formula (XVI) → —General formula (ΧΧΠ)

Examples of the base that can be used in this reaction include alkali metal hydrides such as lithium hydride and sodium hydride, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, sodium hydrogen carbonate, Examples thereof include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, and organic bases such as pyridine and triethylamine. The amount of the base used may be appropriately selected within the range of 2 to 5 times the molar amount of the aminoacetonitrile represented by the general formula (XVI)! The solvent that can be used in this reaction is not particularly limited as long as it does not inhibit this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, alcohols such as methanol, ethanol, and isopropyl alcohol, Ketones such as acetone and methyl ethyl ketone, halogenated hydrocarbons such as chloroform, dichloromethane, ethers such as jetyl ether, tetrahydrofuran and dioxane, acetonitrile, N, N dimethylformamide, N-methylpyrrolidone, Examples thereof include polar solvents such as dimethyl sulfoxide, water, and pyridine.

In this reaction, with respect to the aminoacetonitrile represented by the general formula (XVI), the carbon disulfide is in the range of equimolar to 2-fold mole, and the compound represented by the general formula (XVIII) is 2-fold mole. It can be used by appropriately selecting in the range of ~ 4 times mole.

The reaction temperature may be appropriately selected within the range of room temperature to the boiling point of the reaction solvent. Although the reaction time is not constant depending on the reaction scale and reaction temperature, it may be appropriately selected within the range of 1 to 48 hours.

After the reaction is complete, use 5-1 to isolate the desired product.

7- 2. General formula (ΧΧΠ) → —General formula (I 3g)

The solvent that can be used in this reaction is not particularly limited as long as it does not inhibit this reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, alcohols such as methanol, ethanol, and isopropyl alcohol, Ketones such as acetone and methylethylketone, halogenated hydrocarbons such as chloroform, dichloromethane, ethers such as jetyl ether, tetrahydrofuran and dioxane, acetonitrile, N, N dimethylformamide, N-methylpyrrolidone, Examples include polar solvents such as dimethyl sulfoxide, water, pyridine, etc., but solvents having high solubility in mercabtan metal salts, such as methanol, ethanol, acetonitrile, dioxane, N, N dimethylformamide, N-methylpyrrolidone , Dimethylsulfoxy De is preferred.

Since this reaction is an equimolar reaction, it suffices to carry out an equimolar reaction between the compound represented by the general formula (XXII) and the mercabtan metal salt represented by the general formula (XXIII). Use it.

The reaction temperature may be appropriately selected within the range of room temperature to the boiling point of the reaction solvent. Reaction time Is not constant depending on the reaction scale and reaction temperature, but may be appropriately selected within the range of 1 to 48 hours.

After the reaction is complete, use 5-1 to isolate the desired product.

[0041] 7- 3. General Formula (XVI) → General Formula (I 3f)

In this reaction, 7-1 except that the compound represented by the general formula (XVIII) is used in the range of 0.8-fold to 1.2-fold mole relative to the aminoacetonitrile represented by the general formula (XVI). Same as above.

7-4. General formula (I 3f) → —General formula (I 3g)

As the aryl halide represented by the general formula (XXIV) that can be used in this reaction, a highly reactive substance, that is, an electron-withdrawing substituent is present on the ring, and a fluorine atom or a chlorine atom is used as the halide. Those having the following are preferred. The base, solvent, reaction temperature, reaction time, and isolation method may be the same as in 7-1.

Representative compounds of the acetonitrile derivative represented by the general formula (I) of the present invention that can be produced by the production method are exemplified in Tables 1 and 2, but the present invention is not limited thereto. In Table 1, “Me” represents a methyl group, ¾ represents an ethyl group, “Pr” represents a propyl group, “Bu” represents a butyl group, “Pen” represents a pentyl group, and “Hex” represents Hexyl group, “Oct” is octyl group, “CN” is cyan group, “Ph” is phenol group, “Bn” is benzyl group, “Py” is pyridyl group, “n— "" Means normal, "i-" means iso, "s-" means secondary, "t-" means tertiary, "c-" means cyclo, and "one" means single bond.

[0042] General formula (I 1)

1- 1)

[table 1] Table 1 (R = R = H)

Compound Q ¹ WR ¹ RR ⁵ Melting point (° C) or

No. Refractive index _n D (° C)

1-1 4-CI-Bn S H Me n-Oct

1-2 2-CI-Bn S H Me n-Oct Paste

1-3 4-CI-Bn S H Me t-Bu 112-113 o

1-4 2-CI-Bn S H Me t-Bu 143-144

1-5 2-CI-Bn S H Me i-Bu 103-105

1-6 4-CI-Bn S H Me i-Bu 108-110

1-7 4-CI-Bn 0 H Me 71-74

1-8 4-CF ₃ -Bn 0 H Me 90-91

1-9 4-CF ₃ -Ph 0 H Me n-Bu 130-132

1-10 3,5-Me ₂ -Ph 0 H Me n-Bu Paste

1-11 4-GF ₃ -Bn 0 H Me n-Oct 80-81

1-12 4-GF ₃ -Ph 0 H Me n-Oct 103-105

1-13 4-CF ₃ -Ph 0 H Me n-Hex 115-116

1-14 4-CF ₃ -Bn 0 H Me n-Hex 60-63

1-15 4-CI-Bn 0 H Me n-Hex 82-83

1-16 4-CF ₃ -Bn 0 H Me cinnamyl Paste

1-17 4-CI-Bn 0 H Me cinnamyl Paste

1-18 4-CF ₃ -Bn 0 H Me 2-propynyl

1-19 0 H Me 2-propynyl 107-109

3- (4-CI-Ph)-

1-20 4-GF ₃ -Ph 0 H Me 108-110

2-propynyl

3- (4- C 卜 Ph)-

1-21 4-CF ₃ -Bn 0 H Me Paste

2-propynyl

3- (4- C 卜 Ph)-

1-22 4-CI-Bn 0 H Me Paste

2-propynyl

1-23 4-GF ₃ -Ph 0 H Me PhOCH ₂ CH ₂ 116-118

1-24 4-CF, -Bn 0 H Me PhOCH H, 82-84 2]

[] [0044

Table 1 (continued)

Compound Q ¹ WR ¹ RR ⁵ Melting point (° C) or

No. Refractive index nD (° C)

1-59 4-CI-Bn 0 H Me 4-CI-PhNHCO 158-159

1-60 4-CI-Bn 0 Me Me 4-CI-PhOCH ₂ CH ₂

1-61 4-CF ₃ 0-Bn 0 Me Me PhOCH ₂ CH ₂

〇 ϋ

1-62 3-C OF ₃ 0-Bn O Me Me 4-CI-PhOCH ₂ CH ₂

1-63 2-CF ₃ 0- CLBn 0 Me Me 2-CI-PhOCH ₂ CH ₂

1-64 4-CF ₃ 0-Bn O Me Me 3-CI-PhOCH ₂ CH ₂

1-65 3-CF ₃ 0-Bn 0 Me Me 4-CF ₃ -PhOCH ₂ CH ₂

1-66 4-CF ₃ -Bn 0 Me Me 4-CF ₃ -PhOCH ₂ CH ₂

1-67 4-CF ₃ -Bn O Me Me 4-CF ₃ 0-PhOCH ₂ CH ₂

1-68 O Me Me 3-CF ₃ 0-PhOCH ₂ CH ₂

1-69 2-CF ₃ 0-Bn 0 Me Me 2-CF ₃ 0-PhOCH ₂ CH ₂

1-70 4-CN-Bn 0 Me Et i-BuOCH ₂ CH ₂

1-71 4-CN-Bn 0 Me Et cinnamyl

1-72 4-CF ₃ -Ph O Me Et cinnamyl

1-73 O Me Et 4 G G cinnamyl

1-74 O Me Et 4-CI-cinnamyl

m

1-75 4-CF ₃ 0-Ph OH Et 4— Me-cinnamyl

1-76 3-CF ₃ 0-Ph OH Et 4 C

1-78 4-CN-Ph 0 H n-Pr n-Oct

1-80 2-CN-Ph OH i-Pr EtSCH ₂ CH ₂

1-81 4-CF ₃ -Ph 0 H i-Pr MeSOCH ₂ CH ₂

1-82 4-CF ₃ -Ph 0 Et i-Pr c-HexOCH ₂ CH ₂

1-83 4-CF ₃ -Ph 0 Et i-Pr c-PenOCH ₂ CH ₂

1-84 4-CF ₃ -Ph 0 Et c-Pr i-PrOCH ₂ CH ₂

1-85 4-CI-Ph 0 Et c-Pr i-PrOCH ₂ CH ₂

1-86 4-CI-Ph 0 Et c-Pr

1-87 4-Me-Ph 0 Et c_P 「n-Bu

1-88 3-Me-Ph 0 i-Pr i-Bu

1-89 3-Me-Ph 0 i-Pr i-Bu 3- (4-Me-Ph)-2-propynyl

1-90 2-Me-Ph 0 i-Pr i-Bu 3- (3-C to Ph)-2- propynyl

1-91 2-Me-Ph 0 i-Pr i-Bu 3- (2-C to Ph) _2-propynyl Table 4] Table 1 (continued)

Compound Q ¹ WR ¹ RR ⁵ Melting point (° C) or

No. Refractive index nD (° C)

1-92 4-t-Bu-Ph 0 n-Bu c-Pen PhSCH ₂ CH ₂

1-93 3-t-Bu-Ph 0 c-Pen 4 -CF ₃ -PhOCH ₂ CH ₂

1-94 3-Py 0 n-Bu c-Pen 4 -CF ₃ -PhOCH ₂ CH ₂

1-95 4-Py 0 c-Pen 4- CF ₃ 0-PhOCH ₂ CH ₂

1-96 2-Py 0 MeOCH ₂ c-Pen PhSOCH ₂ CH ₂

1-97 5-C 2-Py 0 MeOCH ₂ Me PhS0 ₂ CH ₂ CH ₂

1-98 5-G G 2-Py 0 MeOCH ₂ Et 4- CF ₃ 0-PhOCH ₂ CH ₂

1-99 4-t-Bu-Bn 0 MeOCH ₂ c_P 3- CF ₃ 0-PhOCH ₂ CH ₂

1-100 4-t-Bu-Bn 0 MeOCH, i-Pr 2- CF ₃ 0-PhOCH ₂ CH ₂

m

[0046] General formula (I 1) W 1 R ⁵ (ii)

[0047] [Table 5]

ccho np—l C 4TronI

≠≠ (^ n

Table 3

1 6 2 Melting point (° c)

No. QR ¹ RRQ or nD bar. C)

3-1 Ph H Me Me Ph

3-2 Ph H -CH2CH2- 4-Cl-Ph 135

3-3 3-I-Ph H Me Me 4-CF ₃ -Ph

3-4 4-GF ₃ _Ph H Et Me 2-Cl-Ph

3-5 3-Cl-Ph H -CH2CH2- 4-Cl-Ph 144-145

3-6 4-Cl-Ph H H H 4-Cl-Ph

3-7 4-Cl-Ph H Me Me 4-Cl-Ph Paste

3-8 4-Cl-Ph H Cri2CH _2-4 -Cl-Ph 172-175

3-9 4-Cl-Ph H jig C i: r 4-Cl-Ph 175-178

3-10 2-CF ₃ -Ph H -CH ₂ CH ₂ -4-Cl-Ph Paste

3-11 2,4-Cls-Ph H Me Me 4-CF ₃ -Ph

3-12 4-Cl-Ph HH 6-Cl-3-PyCH ₂ Me Paste

3-13 4-Cl-Ph H CH2— CHCH ₂ Me 4-Cl-Ph

3-14 4-Cl-Ph H CH≡CCH ₂ Me 4-Cl-Ph

3-15 4-Cl-Ph H PhCH ₂ Me 4-Cl-Ph

3-16 4-Cl-Ph H 2-Cl-PhCH ₂ Me 4-Cl-Ph

3-17 4-Cl-Ph H 3-Cl-PhCH ₂ Me 4-Cl-Ph 7]

[¾] s0

t

[]

4PhCl--

General formula (I 3)

(1-3)

1 2 2 Melting point (° c)

No. Ar G R R Ar

(Or nD ° C)

4-1 Ph NH Me Me Ph

4-2 2-F-Ph 丽 Me Me 4-Cl-Ph

4-3 3-I-Ph NH Me Me 4-CF ₃ -Ph

4-4 4-CF ₃ -Ph NH Et Me 2-Cl-Ph

4-5 2-Cl-Ph NH Me Me 3-Br-Ph

4-6 3-Cl-Ph NH Me Me 4-CF ₃ -Ph

4-7 4-Cl-Ph NH H Me 4-Cl-Ph 104-105

4-8 4-Cl-Ph NH Et Me 4-F-Ph

4-9 4-Cl-Ph NH Me Me 4-Cl-Ph 127-128

4-10 4-Br-Ph NH Me Et 3-CF ₃ -Ph

4-11 2,4-Cl ₂ -Ph NH Me Me 4-CF ₃ -Ph

4-12 4-Cl-Ph NH i-Pr Me 4-Cl-Ph 145-146

4-13 4-Cl-Ph NH

Me 4-Cl-Ph 73

4-14 4-Cl-Ph NH CH≡CCH ₂ Me 4-Cl-Ph 90-92

4-15 4-Cl-Ph NH PhCH ₂ Me 4-Cl-Ph 108-109

4-16 4-Cl-Ph NH 2-Cl-PhCH ₂ Me 4-Cl-Ph 115-117

4-17 4-Cl-Ph NH 3-Cl-PhCH ₂ Me 4-Cl-Ph 109-110 10]

§

»» Knowledge () ^ 4 Table 4 (continued)

Melting point (° c)

No. Ar G R E Ar

(Or nD ° C)

4-39 4-Cl-Ph ― 2-Cl-PhCH ₂ Et 4-Cl-Ph

4-40 4-Cl-Ph ― 3-Cl-PhCH ₂ i-Pr 2-CF ₃ -Ph

4-41 4-Cl-Ph-4-C-res PhCH ₂ Me 2,4-Cl ₂ -Ph

4-42 2-F-Ph ― Me Et 4-Ph-Ph

4-43 4-Cl-Ph S Me Et 4-Cl-Ph

4-44 4-Cl-Ph s Me i-Pr 4-CFg-Ph

4-45 4-Cl-Ph s Et Me 4-Cl-Ph

4-46 2-F-Ph s Me Et 4-Cl-Ph

4-47 3-Cl-Ph s Me i-Pr 4-CFg-Ph

4-48 4-OCF ₃ -Ph s Et Me 4-Cl-Ph

4-49 3-Cl-Ph s Me i-Pr 4-OPh-Ph

4-50 4-OCF ₃ -Ph s Et Me 3-Cl-2- (2,4-Cl ₂ -PhO) Ph

4-51 4-Cl-Ph NH CNCH ₂ Me 4-Cl-Ph 135-140

(Me) ₃ CC Three C

4-52 4-Cl-Ph NH Me 4-Cl-Ph 82-83

-CH = CHCH ₂ Tables 1 to 4 show the ¹ H-NMR data of the compounds indicated as pasty.

[Table 12]

/ v: / O / 6sS00ifcl £ 90sAV ZL

εΐooss

s (dd) 'uijSI¾L / IOOaH) aNH-T ₁ When used as an agricultural and horticultural insecticide, it is suitable for controlling various pests such as paddy rice, fruit trees, vegetables, other crops, turf, trees and flowers, horticultural, horticultural, stored pests, sanitary pests, nematodes, etc. , For example, Adoxophyes orana fasciata, Adoxophyes sp., Archips fuscocupreanus, Grapholita inopinata, Graphisita molpon, Monis ), Mannkui J (Leguminivora glycinivorella), Kuhaku Hamaki (Olethreutes mori), Chiyanohosoga (Caloptilia thevivora), Apple Hosoga (Calop tina zachrysa), Nymphoso sword (Phyllonorycter nngoniella), nanhoso a rap crucivora), Otano-ku (Heliothis sp.), Kodlinga (Laspeyresia pomonella), Kona (Plutella xylostella), Arg yresthia conjugella, Futari Meif J (and hilo suppressalis), Knotomeif J (Empestia elutella), Glyphodes pyloalisaga (Glyphodes pyloalisaga) incertulas), Parnara guttata, Pseudaletia separata, Sesamia inferens, Hellulla undal is, Papilio xuthus, Olicarema neust (Malacosoma neust) Lohitri (Hyphantria cunea), Shino-ttoga (Parapediasia teterrella), Scots selenaria (A scotis selenaria), Grapeberi moss (Endopiza viteana), Lymone moth molyssa Agro tis segetum), Autographa nignsigna, Mames tra brassic ae), leopard, Spodoptera litura, Lepidoptera (Spodoptera exigua), etc.,

Macrosteles fascifrons, Nephotettix cincticeps, Tobirounka (Nilaparvata lugens), White-footed plant (Sogatella forcifera), Citrus whales (Diaphorina citri), Grae-bola taiko White-tailed lice (Trialeurodes vaporariorum), Black-tailed pea aphid (Lipaphis erysimi), Momomo Zofumun (Myzus persicae), Green-headed weevil (Eropiastes ceriferus li, Citrus stag beetle (Pulvinaria aurantu li) , Japanese stock beetle (Comstockaspis perniciosa), Yanonekai 7 Hemiptera such as Unaspis yanonensis, Pratylenchus sp., Anomala rufocuprea, Popilla japonica, Tobacco la sioderma serncorne, Neuftus b , Ninjahon Anto (E pilachna vigintiotopunctata, "7 zu ³ r Caliosobruchus chinensis) ), Urino, Mun (A ulacophora femoralis), Oulema oryzae, = Phyllotre ta striolata, Pinus periwinkle (Tomicus piniperda), Colorado potato beetle (Leptinota rsa decemlineata) Coleopterous pests such as beetroot (Epilachna varivestis) and corn nolate worms (Diabrotica sp.),

[0058] Uri Noe (Dacus (Zeugodacus) cucurbitae), Force Nko Noe (Dacus (Bactrocera) dorsal is), Ine no Mogi (Agromyza oryzae), Onioneginoe (Delia antiqua), Tanenoe (D alia) platura), Taisasatamanokue (Asphondylis sp.), Yenokue (Musca domestica), Diptera pests such as Culex pipiens pipiens, Pratyl enchus coffeae, Potato cyst centipede ( Insects such as Glabodera rostchiensis, Meloidogyne sp., Tylenchulus semipenetrans, Aphelenchus avenae, and Aphelenchoides ritzemab ◦si It has an insecticidal effect and is particularly active against lepidopteran pests.

[0059] In use, it is common to formulate and use in a convenient shape according to a conventional method for agricultural chemical formulations. That is, the acetonitrile derivative represented by the general formula (I) is dissolved, pulverized, separated, suspended, mixed in an appropriate inert carrier, or if necessary, together with an auxiliary agent. Emulsification, mixing, impregnation, adsorption, inclusion, encapsulation or adhesion, appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable powders, granules, powders, tablets, pastes, These can be used in the form of a bait agent, smoke agent, etc. These can be used in the form of being packaged in an appropriate material such as a water-soluble polymer, such as a knock agent or jumbo agent.

[0060] The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can be used as a body carrier include soy flour, cereal flour, wood flour, husk flour, saw flour, octopus stalk flour, tarmi husk flour, bran, fiber powder, residue after extraction of plant extracts, and pulverization Synthetic polymers such as synthetic resins, clays (eg kaolin, bentonite, acid clay), talcs (eg talc, pyrophyllite, etc.), silicas (eg diatomaceous earth, silica sand, mica, white carbon (hydrous fine silicon, Synthetic, highly dispersed silicic acid, also called hydrous silicic acid, may contain calcium silicate as the main component depending on the product.)}, Activated carbon, powder, pumice, calcined diatomaceous earth, brick ground, fly ash, sand, potassium salt , Inorganic mineral powders such as calcium carbonate and calcium phosphate, plastic carriers such as polyethylene, polypropylene, and polysalt / vinylidene, ammonium sulfate, ammonium phosphate, ammonium nitrate, urine , Fertilizer salts depreciation etc., can be exemplified compost or the like, these are used alone or in the form of a mixture of two or more.

[0061] As materials that can be used as a liquid carrier, in addition to those that have solvent ability themselves, those that do not have solvent ability but can disperse the active ingredient compound with the aid of an auxiliary agent are selected. For example, the following carriers can be exemplified as typical examples, but these are used alone or in the form of a mixture of two or more thereof, such as water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc. ), Ketones (eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.), fat Aromatic hydrocarbons (eg kerosene, mineral oil), aromatic hydrocarbons (eg benzene, Ruene, xylene, solvent naphtha, alkylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloroethane, chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, di) Octyl phthalate, etc.), amides (eg, dimethylformamide, jetylformamide, dimethylacetamide, etc.), nitriles (eg, acetonitrile, etc.), dimethyl sulfoxides, and the like.

[0062] As other adjuvants, typical adjuvants exemplified below can be mentioned, and these adjuvants are used depending on the purpose, and in some cases, two or more kinds of adjuvants are used. It can be used in combination, or in some cases, no adjuvants can be used at all. Surfactants are used for emulsification, dispersion, solubilization and Z or wetting purposes of active ingredient compounds, for example polyoxy Siethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene succinate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate Further, surfactants such as naphthalene sulfonic acid condensate, lignosulfonate, and higher alcohol sulfate can be exemplified. Further, for the purpose of stabilizing the dispersion of the active ingredient compound, sticking and Z or bonding, the following auxiliary agents can be used, such as casein, gelatin, starch, methylcellulose, carboxymethylcellulose, gum arabic, Adjuvants such as polybulal alcohol, pine oil, coconut oil, bentonite and ligne sulfonate can also be used.

[0063] In order to improve the fluidity of the solid product, the following adjuvants may be used, and for example, adjuvants such as waxes, stearates and alkyl phosphates may be used. As a peptizer for the suspension product, for example, auxiliary agents such as naphthalene sulfonic acid condensate and condensed phosphate can be used. As the antifoaming agent, for example, an auxiliary agent such as silicone oil can be used. The blending ratio of the active ingredient-compound can be adjusted as necessary.For example, 0.01 to 50% by weight when it is used as a powder or granule, and 0. 01 to 50% by weight is suitable.

[0064] In order to control various pests, the pest control agent of the present invention formulated as described above is used in an amount effective for pest control as it is, or appropriately diluted with water or suspended. It can be used by applying to crops where the occurrence of pests is expected or where the occurrence is undesirable. Cell trays, seedling boxes, paddy fields, fields, fruit pods, vegetables, other crops, paddy field water such as flower baskets, soil, etc. before the occurrence of pests or when they are confirmed The plant pest cultivation carrier, seeds, stems, leaves, flowers, etc., or the traps treated with passages, attractants, pigments, etc. that are assumed to be visited by pests, are used for the pests of the present invention. The desired effect of the control agent is exhibited. The plant to be applied may be a conventional plant or a plant to which normal breeding such as crossing is added, and genetically modified plants (for example, herbicide resistance genes, pest resistance genes, insecticidal peptide genes) Plants that have been introduced with genes that increase the yield of specific components such as oil and fat components, etc.), improved taste crops, protoplast fusion, etc. A plant in which multiple varieties are fused (for example, a plant in which pomato tomato and potato are fused), a plant that has been subjected to disease resistance treatment by inoculation with an attenuated strain or gene, and the like may be used. Depending on these properties, a synergistic effect with the compound of the present invention can be expected. The amount of the harmful organism control agent of the present invention depends on various factors such as the purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. Although it fluctuates, it may be appropriately selected depending on the purpose from the range of 0.1 lg to 10 kg per 10 are as an active ingredient compound. The pest control agent of the present invention can be further used in combination with other agricultural and horticultural pest control agents for the purpose of controlling the pests to be controlled, the appropriate control period, or for reducing the dose.

[0065] When used as an animal parasite control agent, animals such as cattle, horses, sheep, etc., pets such as dogs, cats, etc., as well as rodents such as mice, rats, rats, musters, squirrels, etc. Can be used against animals, maggots, carnivorous animals such as ferrets, birds such as ducks, birds and pigeons, and animal parasites ii, f rows? J cat fleas (tenocephalides felis), yinuno ^ (tenocephalides cams, fleas such as Xenopsylla cheopis); Parasitic parasites such as lice infestations such as ematopinus eurysternus) and damselfly (Damalinia ovis) can be shown in column f.

[0066] In order to efficiently use the animal parasite control agent comprising the acetonitrile derivative represented by (I) of the present invention as an active ingredient, a suitable solid carrier is generally used according to a commonly used pharmaceutical formulation. And z or a liquid carrier, etc., and if necessary, admixed in an appropriate ratio together with an auxiliary agent, etc., dissolved, suspended, mixed, impregnated, adsorbed or adhered, and used in an appropriate dosage form according to the purpose of use, such as a liquid agent, Prepare and use emulsions, creams, ointments, suspensions, and aerosols.

As the solid carrier or the liquid carrier used in the present invention, it is preferable to use a liquid carrier because it is easy to process the target animal if a carrier usually used for animal drugs is used. Examples thereof include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol, and benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, and water. Of the present invention As the control agent, an auxiliary agent can be used as necessary, and a surfactant, an antioxidant, an emulsifier, etc. can be used as the auxiliary agent, for example, polyoxyethylene alkyl aryl ether, polyoxyethylene sorbitan. Monolaurate, alkylaryl sorbitan monolaurate, alkylbenzene sulfonate, alkyl naphthalene sulfonic acid, lignin sulfonate higher alcohol sulfate ester, glycol monoalkyl ether, glycols and other surfactants, mono oleic acid Examples include sorbitans such as sorbitan, sorbitan monolaurate, monopreric acid monophosphate, monomonoglyceride monopurine, isostearic acid monoglyceride, propylene glycol monopolypropylate, and acid-detergents such as BHA and BHT. it can. The control agent of the present invention can be blended in an amount of 0.01 to 80. 0 parts by weight as an active ingredient in 100 parts by weight of the control agent.

The animal parasite control agent of the present invention formulated as described above is usually a spot-on treatment for controlling parasitic pests by dripping a liquid drug onto the skin of the back of the shoulder of the subject animal. By treating the liquid drug along the back line of the target animal body and diffusing the treated drug on the body surface, it can be used by local treatment methods such as pour-on treatment to control parasitic pests. In addition to this, there are a treatment method in which a medicine is carried on a collar and the medicine is released, a treatment method in which a liquid or ointment medicine is directly applied to the body surface, a method in which a liquid aerosol medicine is treated by spraying, etc. . The applied dose may be appropriately selected from the range of usually about 0.1 to 500 mg as an active ingredient compound and usually about 0.01 to 20 ml as the control agent of the present invention per 1 kg body weight of the subject animal. It is also possible to control parasites in the animal body by administering a diet. Furthermore, the animal parasite control agent of the present invention can be used in combination with other active ingredients as necessary. For example, permethrin, phenothrin, allethrin, pyrethrin, praretrin, siphenothrin, sifenoretrin, fenvalerate, phenpropatoline. Pyrethroid compounds such as transfluthrin, dichlorvos, tetrachlorophine binphos, organophosphorus compounds such as fenthion, chlorpyrifos, and diazinon, N-phenol birazole compounds such as fiprole, proboxil, force valil, methoxadiazone, and funocarp Examples thereof include carbamate compounds, neonicotinoid compounds, and the like.

Example [0068] Representative examples, formulation examples and test examples of the present invention are shown below, but the present invention is not limited thereto. In the preparation examples, “parts” means “parts by weight”.

Example 1. Production of N- (1-cyanol 1-methyl-2-octylthioethyl) -4 chlorophenylacetamide (Compound No. 1-1)

Dissolve 0.92 g (9.95 mmol) of 1-octanethiol and 1.46 g (9.98 mmol) of 1-octanethiol in 20 ml of tetrahydrofuran, add 1.10 g (10.9 mmol) of triethylamine at room temperature, Stir for 1 hour. After completion of the reaction, insoluble matters were filtered out, the solvent was distilled off, and octylthioacetone was obtained quantitatively. The obtained compound was used for the next reaction without purification. 4.04 g (20.0 millimonoles) of acetone was dissolved in 20 ml of methanol and 1.00 g of sodium cyanide (20.4 mmol), salt Anammoum 1.60 g (29.9 mmol), an excess amount of 28% aqueous ammonia was added, and the mixture was stirred overnight at room temperature. Methanol was distilled off, followed by extraction with ethyl acetate to obtain 4.06 g (yield 94%) of 2-amino-2-methyl-3-octylthiopropane-tolyl.

2-Amino 2-methyl-3-octylthiopronon- 卜 ryl 0.46 g (2.00 mmol), 4-cholephenol acetate chloride 0.38 g (2.01 mmol) were dissolved in 10 ml of tetrahydrofuran. Then, 0.22 g (2.18 mmol) of triethylamine was added dropwise under ice cooling. After stirring at room temperature for 3 hours, water was added to the reaction solution, extracted with ethyl acetate, and purified by silica gel column chromatography (ethyl acetate-hexane) to obtain 0.48 g of the objective compound.

Yield: 70%

Physical property: Melting point 85 ~ 86 ° C

Example 2. Production of N— (l cyano-1-methyl-2-octyloxychetyl) -4 trifluoromethylphenylacetamide (Compound Nos. 1-11)

Hydrogenadicum (purity 60%) 1. 20 g (30.0 midimonore) was suspended in 200 ml of dimethinorenolememia and 2.28 g (30.0 mmol) of 1,2 propanediol was added. 7.20 g (30.0 mmol) of octyl iodide was added and stirred at 100 ° C. for 7 hours. The reaction solution was cooled to room temperature, poured into ice water, neutralized with concentrated hydrochloric acid, and extracted with ethyl acetate. The resulting crude product was purified by silica gel column chromatography (ethyl acetate-hexane). 1-methyl 2-octyloxyethanol 2.48 g (44% yield) was obtained.

2.84 g (20.0 mmol) g of phosphoric acid pentalin and 2.34 g (30.0 mmol) of dimethyl sulfoxide are dissolved in 20 ml of dimethylformamide and stirred at room temperature with 1-methyl-2-octyloxyethanol 1 88 g (10.0 mmol) was added dropwise. After stirring for 3 hours, 5.05 g (50.0 mmol) of triethylamine was added dropwise, and the mixture was further stirred for 30 minutes. The reaction solution was poured into ice water, extracted with ethyl acetate, and purified by silica gel column chromatography (ethyl acetate-hexane) to obtain 1.26 g (yield 68%) of octyloxyacetone.

Octyloxyacetone 0.93g (5.00 mmol) is dissolved in methanol 10ml, cyanogen 0.25ml (5.10mm mono), salt monmonum 0.40g (7.48mm monole), Overload [J amount of 28% ammonia water was added and stirred overnight. Methanol was distilled off and extracted with ethyl acetate to obtain 0.93 g (yield 88%) of 2-amino-2-methyl-3-octyloxypropane-tolyl.

The obtained 2-amino-2-methyl-3-octyloxypropane-tolyl 0.42 g (l. 98 mmol), 4-trifluoromethylphenol acetic acid chloride 0.44 g (l. 98 mmol) It was dissolved in 10 ml of tetrahydrofuran, and 0.22 g (2.18 mmol) of triethylamine was added dropwise under ice cooling. After stirring at room temperature for 3 hours, water was added to the reaction solution, extracted with ethyl acetate, and purified by silica gel column chromatography (ethyl acetate-hexane) to obtain 0.46 g of the objective compound.

Yield: 58%

Physical property: Melting point 80 ~ 81 ° C

Example 3. Production of N— {2— [3— (4 black-mouthed phenol) 2 propyloxy] 1 cyano-1-methylethyl} -4 trifluoromethylbenzamide (Compound No. 1-20)

Hydrogenate Dicum (Purity 60%) 1. Suspend 20 g (30.0 Midimonore) in 200 ml Dimethinolehonolememia, 2. 28 g (30.0 mmol) 1,2 propanediol, I made a mess of sodium bromide. Prono Noregino Lebromide 3. 57 g (30.0 Midi Monole), 100. Heated at C for 7 hours. After completion of the reaction, the reaction solution was returned to room temperature, poured into ice water, neutralized with concentrated hydrochloric acid, and extracted with ethyl acetate. The obtained crude product was subjected to silica gel column chromatography (acetic acid 1-methyl-2 propargyloxyethanol 1.43 g (yield 42%) was obtained.

1-methyl-2 propargyloxyethanol 1.14 g (10.0 mmol), 4 chloroiodobenzene 2.38 g (10.0 mmol), dichlorobis (triphenylphosphine) no << radium 0.05 g ( 0.071 millimonoles) and 0.025 g (0.13 millimonoles) of Yowi cupron were suspended in 10 ml of triethylamine and stirred overnight at room temperature. After completion of the reaction, insoluble matter was filtered off and the solvent was distilled off. The resulting crude product was purified by silica gel column chromatography (ethyl acetate-hexane) to give 1-methyl 2- [3- (4-cyclohexane) -2-propylvinyl] ethanol 1.67 g (Yield 74%) was obtained.

Dissolve 1.42 g (10.0 mmol) of pentalin phosphonate and 1.17 g (15.0 mmol) of dimethylsulfoxide in 20 ml of dimethylformamide and stir at room temperature. 1-Methyl-2- [3— (4 1) 2-propyloxy] ethanol (1.12 g, 4.99 mmol) was added dropwise. After stirring for 3 hours, 2.03 g (2.01 mmol) of triethylamine was added dropwise, and the mixture was further stirred for 30 minutes. The reaction mixture was poured into ice water, extracted with ethyl acetate, and then purified with silica gel column chromatography (ethyl acetate-hexane) [3- (4-chlorophenyl) 2-propyloxy] acetone 0.93 g (yield). 84%).

[3— (4 black-mouthed phenol) -2 propylene] 0.56 g (2.52 mmol) of acetone was dissolved in 10 ml of methanol, 0.125 g (2.55 mmol) of sodium cyanide, -UM 0.20 g (3.74 mmol), excess 28% aqueous ammonia was added and stirred overnight. Methanol was distilled off, extracted with ethyl acetate, 2-amino-3- [3- (4-chlorophenol) -2-propyloxy] -2-methylpropane-tolyl 0.59 g (93% yield) ) 2 Amino 3- [3— (4-Florophenyl) 2 Propoxy] —2-Methylproton-tolyl 0.50 g (2.00 mmol), 4 Trifluoromethylbenzoic acid chloride 0.42 g (2.01 millimoles) of terahydrofuran (10 ml) was dissolved, 0.28 g (2.18 mmol) of rietinoleamine was added, and the mixture was stirred for 3 hours. Insoluble matter was filtered off, the solvent was distilled off, and the residue was purified by silica gel chromatography (ethyl acetate-hexane) to obtain 0.58 g of the objective compound.

Yield: 69%

Physical properties: melting point 108 ~ 110 ° C Example 4 N- [2- (4-Chromium 1-cyanol 1-methylethyl)]-4-trifluoromethylbenzamide (Compound No. 1-57) Production: Hydroxyacetone 0.74 g (10.0 mmol), 4-chlorophenol isocyanate 1.54 g (10.0 mmol) was dissolved in 20 ml of tetrahydrofuran, and 1 drop of triethylamine was added and stirred at room temperature overnight. Then, the solvent was distilled off to obtain 2.10 g (yield: 92%) of 4-black-mouthed phenaminocarbo-loxyacetone.

4. Add 20.0 g (9.23 mmol) of black-mouthed phenolaminooxyacetone to 20 ml of methanol and add cyanide !; um 0.50 g (10.2 midimonore), salty ammonium salt 0.80 g (15.0 mmol) and 28% aqueous ammonia (10 ml) were added, and the mixture was stirred for 2 days. The solvent was distilled off, and the mixture was extracted with ethyl acetate to obtain 1.62 g (yield: 64%) of 2-amino-3- (4-chloro-phenylaminocarboxy) -2-methylpropane-tolyl.

The resulting 2-amino-3- (4-cyclohexane-amino-carboxyloxy) 2-methylpronino nitrinole 0.52 g (2.05 millimonole) was dissolved in 10 ml of tetrahydrofuran, and water-cooled to give 4-trifluoromethylbenzoate. 0.42 g (2.01 mmol) of acid chloride and 0.30 g of triethylamine were successively added dropwise. After completion of the dropwise addition, the mixture was stirred overnight at room temperature, water was added to the reaction mixture, the solvent was distilled off under reduced pressure, and the mixture was extracted with ethyl acetate. Purification by silica gel column chromatography (ethyl acetate-hexane) gave 0.66 g of the target compound.

Yield: 70%

Physical property: 160-162 ° C

[0073] Example 5. N— [1-Cyanol 2- (2, 6 dimethylmorpholino) 1-methylethyl]

-Manufacture of 2, 6 diclonal pyridine-4 carboxamide (Compound No. 2-4)

Acetone 13.9 g (150 mmol) and Yowi potassium 0.3 g (l.8 mmol) were placed in 20 ml of acetone and left overnight. Acetone solution of 1,5 g (99.8 millimonole) of 2,6 dimethylenomonomonophorin and 3.5 g (25.4 mmol) of anhydrous potassium carbonate was heated to reflux, and 1/4 of the chloroacetone solution was added dropwise thereto. Anhydrous potassium carbonate (3.5 g, 25.4 mmol) was added again, and a 1/4 acetone solution was added dropwise. Similarly, this operation was repeated twice more, and then the mixture was heated to reflux for 6 hours. After cooling the reaction solution, the inorganic material was filtered off and the filtrate was concentrated. Decolorization was performed by adsorption on silica gel to obtain 15.2 g (yield 89%) of 2,6 dimethylmorpholinoacetone. Dissolve 8.55 g (50.0 mmol) of 2,6-dimethylmorpholinoacetone, 2.50 g (51.0 millimonoles) of cyanogen sodium, 4.00 g (74.8 millimonoles) of salt and ammonium salt in 50 ml of methanol. Then, an excess amount of 28% ammonia water was added and stirred for a whole day and night. Evaporation of the solvent and extraction with ethyl acetate gave 8.37 g of 2-amino-3- (2,6 dimethylmorpholino) -2-methylpropane-tolyl (yield 85%) o

2,6dichloropyridine-4-carboxylic acid 0.39 g (2.03 mmol), 2-amino 3- (2,6 dimethylmorpholino) -2-methylpronon-tolyl 0.40 g (2.03 mmol), iodine (2) Black mouth 1-methinorepyridinum 0.57 g (2.23 millimonole) and triethinoleamine 0.23 g (2.28 mmol) were dissolved in 10 ml of acetonitrile and heated to reflux for 3 hours. Water was added to the reaction solution and the mixture was extracted with ethyl acetate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain 0.40 g of the objective compound.

Yield: 53%

Physical properties: ¹ H—NMR (CDC1 ZTMS, δ value ppm)

Three

7. 83 (1H, br), 7. 56 (2H, s), 3. 78—3.55 (2H, m),

3.14 (1H, d), 2.99 (1H, d), 2.70 (1H, d),

2. 69 (1H, d), 2. 24 (1H, t), 2. 07 (1H, t),

1. 83 (3H, s), 1. 18 (6H, m)

Example 6. Production of N— [2— (4-Chromium Fue-Noremino) 1-Ciano 1-Methylenole 2-Methylthioethyl] -4 Chromium Benzamide (Compound No. 3-7)

2 Aminopropio-tolyl (7.21 g, 103 mmol) was suspended in pyridine (100 ml), 4-chlorobenzoic acid chloride (15.0 g, 85.7 mmol) was added, and the mixture was stirred at 70-80 ° C for 3 hours. The reaction mixture was concentrated, ethyl acetate was added, and the mixture was washed with saturated aqueous potassium carbonate. The ethyl acetate layer was washed with water and concentrated, and the resulting solid was washed with a mixed solvent of hexane-jetyl ether, and N- (1-cyanoethyl) -4 black benzoic acid amide (9. lg, 51% yield) ) Diisopropylamine 1.94 g (19.2 mmol) and n-butyllithium hexane solution (1.6 M) 10 ml (16 mmol) The prepared lithium diisopropylamide solution was cooled with dry ice / acetone and 10 ml of tetrahydrofuran was added. After preparation, N— (1-Cyanoethyl) 4 -cyclobenzoic acid amide prepared by the above method 1.04 g (4.98 mmol), isothiocyan A solution obtained by dissolving 0.84 g (4.96 mmol) of acid 4 black-mouthed solution in 10 ml of tetrahydrofuran was added dropwise. After stirring for 1 hour under cooling, a solution of 0.71 g (5.0 mmol) of methyl iodide dissolved in 10 ml of tetrahydrofuran was added dropwise, and the mixture was warmed to room temperature and stirred for 3 hours. Saturated ammonium water was added to the reaction solution, followed by extraction with ethyl acetate, washing with water, and concentration. The obtained solid was washed with a mixed solvent of ethyl acetate-jetyl ether, and insolubles were filtered off. The mouth liquor was concentrated and purified by silica gel column chromatography (ethyl acetate-hexane mixed solvent) to obtain 1.18 g of the objective compound.

Yield: 61%

Physical properties: ¹ H—NMR (CDC1 ZTMS, δ value ppm)

Three

7. 75 (2H, d), 7. 43 (2H, d), 7. 35 (2H, d),

6. 70 (2H, d), 2. 17 (3H, s), 2.04 (3H, s)

Example 7. Preparation of N— [2- (4 Kuroguchi Fe-Ruimino) 3 Cyantetrahydrothiophene 3-yl] -4 Chloro Benzamide (Compound No. 3-8)

10.8 g (103 mmol) of aminoacetonitrile sulfate was suspended in 100 ml of pyridine, 15.0 g (85.7 mmol) of 4-chlorobenzoic acid chloride was added, and the mixture was stirred at 70 to 80 ° C. for 3 hours. The reaction mixture was concentrated, ethyl acetate was added, and the mixture was washed with saturated aqueous potassium carbonate. The ethyl acetate layer was washed with water and concentrated, and the resulting solid was washed with a mixed solvent of hexane-jetyl ether to obtain N-cyanmethyl-4-chlorobenzoic acid amide (9.6 g, yield 58%). It was.

Diisopropylamine 1.94 g (19.2 mmol) and n-butyllithium hexane solution (1.6 M) 10 ml (16 mmol) The prepared lithium diisopropylamide solution was cooled with dry ice / acetone and 10 ml of tetrahydrofuran was added. After preparation, 0.97 g (4.98 mmol) of N-cyanomethyl-4-chlorobenzoic acid amide prepared by the above method and 0.84 g (4.96 mmol) of isothiocyanic acid 4 chloroform were added to 10 ml of tetrahydrofuran. The dissolved solution was dropped. After stirring for 1 hour under cooling, a solution prepared by dissolving 0.94 g (5.0 mmol) of dibromoethane in 10 ml of tetrahydrofuran was added dropwise, and the mixture was warmed to room temperature and stirred for 3 hours. Saturated ammonium chloride water was added to the reaction solution, followed by extraction with ethyl acetate, washing with water, and concentration. The obtained solid was washed with an ethyl acetate-jetyl ether mixed solvent, and insoluble matters were filtered off. Concentrate the mouth liquor and purify it with silica gel column chromatography (ethyl acetate-hexane mixed solvent). 0.68 g of compound was obtained.

Yield: 23%

Physical property: Melting point 172 ~ 175 ° C

Example 8. 1— [2— (4-Chlorophenoxy) 1-cyanol 1-methylethyl] —3— (4-cylinder phenol) thiorea (Compound No. 4-7) Manufacturing

2-amino 4- (4-chlorophenoxy) 2-methylpropane-tolyl 2.0 g (9.5 mmol), isothiocyanic acid 4-chlorophenol 1.6 g (9.5 mmol) in 10 ml of acetonitrile In addition, the mixture was stirred overnight at room temperature. The reaction solution was concentrated, and the resulting solid was washed with jetyl ether to obtain 2.7 g of the target compound.

Yield: 74%

Physical property: Melting point 104 ~ 105 ° C

[0077] Example 9. 1— [2— (4-Chlorophenoxy) 1-ciano 1-methylethyl] —3— (4-clogous phenol) 2-methylisothiourea (compound) Production of No. 4-9)

1— [2— (4 Chlorophenoxy) 1 Siano 1—Methinoreethinole] 3— (4 Black-Fuel) Thiourea 0.50 g (l. 3 mmol), iodomethyl 0.22 g (l. 6 mmol) ), 0.18 g (l. 3 mmol) of anhydrous potassium carbonate was added to 10 ml of dimethylformamide, and the mixture was stirred at room temperature for 8 hours. The reaction solution was added to water, extracted with ethyl acetate, the solvent was distilled off, and the resulting solid was washed with jetyl ether to obtain 0.27 g of the objective compound.

Yield: 52%

Physical properties: melting point 127-128 ° C

Example 10. N— [2— (4 trifluoromethylphenoxy) 1-ciano 1-methylethyl] -2, 4 Diclonal Benzothioamide (Compound No. 4-31) Manufacturing of

N— [2— (4-Trifluoromethylphenoxy) 1-ciano 1-methylethyl] -2,4 dichlorobenzamide 0.84 g (2.0 mmol), Lawesson's reagent 0.50 g (l. 2 mmol) ) Was dissolved in 20 ml of dioxane and stirred at room temperature overnight. After completion of the reaction, the solvent was distilled off, followed by extraction with ethyl acetate and purification by silica gel column chromatography (ethyl acetate-hexane) to obtain 0.36 g of the objective compound.

Yield: 41% Physical properties: H-NMR (CDC1 ZTMS, δ ppm)

Three

7.63 (1H, d), 7.50 (2H, d), 7.49 (1H, s),

7.35 (1H, d), 6.91 (2H, d), 4.95 (1H, d),

4.22 (1H, d), 1.68 (3H, s)

Example 11. Preparation of 3— (4 chlorophenoxy) 2— (4 black α-methinoretiobenzylidene) amino-2 methylpropane-tolyl (Compound No. 4-32)

N— [2— (4 Chlorophenoxy) 1-ciano 1-methylethyl] -4 Chlorobenzoic acid amide 0.73 g (2.0 millimonoles) was dissolved in 20 ml of N, N-dimethylenolehonolemamide, and then carbonic acid. 0.28 g (2.0 midimonore) of potassium and 0.30 g (2.1 midimonore) yoi methinole were calorie-free and stirred overnight at room temperature. After completion of the reaction, water was added, extracted with ethyl acetate, and purified by silica gel column chromatography (ethyl acetate-hexane) to obtain 0.32 g of the objective compound. Yield: 43%

Physical properties: ¹ H—NMR (CDC1 ZTMS, δ value ppm)

Three

8.23 (2H, d), 7.45 (2H, d), 7.20 (2H, d),

6.79 (2H, d), 4.15 (1H, d), 4.10 (1H, d),

2.71 (3H, s), 1.54 (3H, s)

Formulation example 1.

Compound of the present invention 10 parts

70 parts of xylene

N-Methylolpyrrolidone 10 parts

With polyoxyethylene nonyl phenyl ether

Mixture with calcium alkylbenzenesulfonate 10 parts

The above is mixed and dissolved uniformly to obtain an emulsion.

Formulation example 2.

Compound of the present invention 3 parts

82 parts of clay powder

Diatomaceous earth powder 15 parts

The above is uniformly mixed and pulverized to obtain a powder. Formulation example 3.

Compound of the present invention 5 parts

90 parts of mixed powder of bentonite and clay

5 parts calcium sulfonate sulfonate

The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to obtain granules.

Formulation example 4.

20 parts of the present compound

Kaolin and synthetic highly dispersed silicic acid 75 parts

With polyoxyethylene nonyl phenyl ether

5 parts mixture with calcium alkylbenzenesulfonate

The above is uniformly mixed and ground to obtain a wettable powder.

Test example 1. Insecticidal test against Plutella xylostella.

After 2 days of release, the adult moths and seedlings were spawned and laid eggs. After 2 days of release, the seedlings and cypress seedlings were added to a drug solution diluted with lOOOppm of a drug containing the compound of the present invention as an active ingredient. It was soaked for 30 seconds, air-dried and then left in a constant temperature room at 25 ° C. The number of hatching insects was investigated 6 days after immersion in the chemical solution, the death rate was calculated by the following formula, and the determination was made according to the following criteria. 1 ward, 10 heads, 3 trains. Number of hatching insects in non-treated area Number of hatching insects in treated area

100 Number of hatching insects in the untreated area Criteria. Α ··· Death rate 100%

'·' Death rate 99% ~ 90%

C-'Death rate 89% -80%

D- · 'Death rate 79% to 50% Compound No. 1— 1 to 1 59 , 2-1-2-6, 3-2, 3-5-3-10, 3-12, 3-26, 3-30-3-32, 4-7, 4-9, 4-12-4 — 20, 4-22, 4-23, 4-30 to 4-32, 4-51, 4-52.

Test Example 2. Insecticidal test against Spodoptera litura.

Cabbage leaf pieces (variety: four seasons) were immersed for about 30 seconds in a chemical solution diluted with lOOOppm of the drug containing the compound of the present invention as an active ingredient. After that, it was covered and placed in a constant temperature room at 25 ° C. After 8 days of inoculation, the number of live and dead insects was examined, and the death rate was calculated according to the following formula. 1 ward, 10 heads, 3 trains. Number of surviving insects in the untreated area Number of surviving insects in the treated area

Death rate (%) =

The number of living insects in the untreated group As a result of the above test, the compounds that showed an insecticidal activity of B or higher were compound Nos. 1-1-1 59, 2-1-2-6, 3-2, 3-5-5 3—10, 3—12, 3—26, 3—30 to 3—32, 4—7, 4 —9, 4—12 to 4—20, 4—22, 4—23, 4—30 to 4— 32, 4-51 and 4-52.

[0083] Test Example 3. Insecticidal test against Adoxophyes sp.

After immersing chia leaves in a chemical solution diluted with lOOOppm of a drug containing the compound of the present invention for about 30 seconds, air-dried, placed in a plastic petri dish with a diameter of 9 cm, and inoculated with chinook larvae, 25 ° C, humidity 70 Left in a constant temperature room. The number of live and dead insects was examined 8 days after the inoculation, and the determination was made in the same manner as in Test Example 2. 1 ward, 10 heads, 3 trains.

As a result of the above test, the compounds that showed an insecticidal activity of B or higher were compound Nos. 1-1-1 59, 21-2-6, 3-2, 3-5-3-10, 3— 12, 3—26, 3—30 to 3—32, 4—7, 4—9, 4—12 to 4—20, 4—22, 4—23, 4—30 to 4—32, 4—51, 4-52. Industrial applicability

[0084] The pesticide containing the acetonitrile derivative represented by the general formula (I) of the present invention as an active ingredient is useful as an agricultural or horticultural insecticide or an animal parasite control agent.

Claims

The scope of the claims

[1]-General formula (I)

{Where A is

Wherein Q ¹ is a (C—C) alkyl group, a halo (C—C) alkyl group, (C—C) cycloal

1 6 1 6 3 6

Kill group, halo (c -c) cycloalkyl group, phenol group, same or different

3 6

1 6 1 6

C—C) alkoxy, halo (C—C) alkoxy, (C—C) alkenyl, halo (

1 6 1 6 2 6

C C) alkyl group, (C C) alkyl group, (C C) cycloalkyl group, (C

2 6 2 6 3 6 2

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkyl group

1 6 1 6

Mouth (C—C) alkyl sulfo-loxy group, (C—C) alkyl sulfier group, halo (

1 6 1 6

2 6 2 6

O group, (C—C) alkenylsulfuryl group, halo (C—C) alkulsulfyl group

2 6 2 6

Group, (C—C) alkenyl sulfonyl group, halo (C—C) alkenyl sulfonyl group,

2 6 2 6

(C—C) alkylamino group, same or different di (C—C) alkylamino group

1 6 1 6

Group, (C—C) alkylsulfonylamino, halo (C—C) alkylsulfonylamino

1 6 1 6

Group, (C C) alkylcarbonyl group, halo (C C) alkylcarbonyl group, (C

1 6 1 6 1

6

1 6 1 6 1 6

) Alkoxy group, halo (c—C) alkoxy group, (C—C) alkylthio group, halo (C

1 6 1 6 1

C) alkylthio, (C—C) alkylsulfinyl, halo (C—C) alkyls

6 1 6 1 6

Rufinyl group, (c—C 1) alkylsulfonyl group or halo (C—C 1) alkylsulfone

1 6

, Halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group,

1 6 1 6 1 6

(C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo group

1 6 1 6 1 6

Finyl group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl

1 6 1 6

1 6

Group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo

1 6 1 6 1 6

(C C) alkoxy group, (C C) alkenyl group, halo (C C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C) alkenyl group

2 6 2 6 2 6

Rusulfinyl group, halo (C—C) alkenylsulfinyl group, (C—C) alkenyl

2 6 2 6 Sulfol group, halo (c-c) alkylsulfol group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkyl carbo group, (C C) alkyloxy carbo-

1 6 1 6

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

1 6

, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (

1 6 1 6 1 6

C—C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

2 6 2 6

Sulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6 Honylamino group, halo (C 1 -c) alkylsulfonylamino group, (C—C) alkyl carbonyl

1 6 1 6

Ball group, halo (C C) alkylcarbol group, (C—C) alkyloxycarboxyl

1 6 1 6

6 1 6 1 6 1

) Alkoxy group, (c—C 1) alkylthio group, halo (C—C 1) alkylthio group, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (Cc) alkylsulfier group, (c-c) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (c-c) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C C)

Selected from 1 6 1 6 norsulfonyl group

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C) a

1 6 1 6 alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyl

2 6 2 6 3 6 group, (C—C) alkenyloxy group, halo (C—C) alkoxy group, (C—C

2 6 2 6 1 6

) Alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo-luo

1 6 1 6

Xyl group, halo (C—C) alkylsulfonyloxy group, (C—C) alkylsulfinyl

1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl group,

1 6 1 6

(C—C) alkylsulfonyl group, (C—C) alkylthio group, halo (C—C) a

2 6 2 6

Rufinyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfo group

1 6 1 6 Nylamino group, (C—C) alkylcarbonyl group, halo (C C) alkylcarbonyl

1 6 1 6 Group, (c -c) alkyloxycarbol group, phenol group, the same or different

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

16 alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C)

1 to 6 selected from 1 6 1 6 rusulfonyl group or halo (C C) alkylsulfonyl group

1 6

C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C −

1 6 1 6 1 6 2

C) alkenyloxy group, halo (c-c) alkenyloxy group, (C—C) alkylthio group

6 2 6 1 6

Group, halo (c -c) alkylthio group, (c -c) alkylsulfinyl group, halo (C

1 6 1 6 1

-C) alkylsulfinyl group, (C-C) alkenylthio group, halo (c-c) alkke

6 2 6 2 6 Diruthio, (C—C) alkenylsulfinyl, halo (c -c) alkenylsulfur

2 6 2 6

Ynyl group, (c -c) alkylsulfonyl group, halo (c -c) alkylsulfonyl group, (

1 6 1 6

c -c) alkenylsulfonyl group, halo (c -c) alkenylsulfonyl group, mono (C

2 6 2 6 1

6 1 6

R ¹ is a hydrogen atom, (CC) alkyl group, halo (CC) alkyl group, (CC) al

1 6 2 6 2 6

, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkylcarbo

2 6 2 6 1 6

-Lole group, halo (C—C) alkylcarbol group, phenolecarol group, the same or different

1 6 Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (CC

1 6 1

) Alkyl group, (C C) alkoxy group or halo (C C) alkoxy group

6 1 6 1 6

Substituted full-carbon group having 1 to 5 substituents, (C C) alkoxycal

1 6

A ball group or a halo (C C) alkoxycarbol group is shown. )

1 6

Or

1 6 1 6 1 6

(C—C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

— C) alkyl group, (C C) cycloalkyl group, (C—C) alkoxy group,

6 3 6 2 6

Halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

-Luoxy group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi group

1 6 1 6

Group, (C—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (

1 6 1 6

C—C) alkthio group, halo (C—C) alkthio group, (C—C) alkyl group

2 6 2 6 2 6

Rusulfyl group, halo (C—C) alkulsulfyl group, (C—C) alkenyl

2 6 2 6

Sulfol group, halo (C—C) alkaryl sulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C C) alkylsulfo-lamino group, (C—C) alkyl carbonyl

1 6 1 6

Ball group, halo (C C) alkylcarbol group, (C C) alkyloxycarboxyl

1 6 1 6

6 1 6 1 6 1

C) alkylsulfier group, halo (c-c) alkylsulfier group, (C—C) al

1 6

1 6 1 6

-c) alkoxy group, halo (c-c) alkoxy group, (c-c) alkylthio group, halo

1 6 1 6 1 6

(c -c) alkylthio group, (C—C) alkylsulfier group, halo (c -c) al

1 6 1 6 1 6 Killsulfier group, (C—C) alkylsulfol group or halo (c -c) alkyls

1 6 1 6

6 1 6 1 6 1 6 Lucoxy group, (c -C) alkoxy group, halo (C—C) alkoxy group, (C

2 6 2 6

—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfi group

1 6 1 6 1 6

-Lu group, halo (C—C) alkylsulfier group, (C—C) alkylthio group, halo (

1 6 2 6

C—C) alkylthio group, (C—C) alkenylsulfier group, halo (C—C)

2 6 2 6 2 6 Lukesulfyl group, (C—C) alkylsulfol group, halo (C—C) alkyl

2 6 2 6

1 6 1 6

Group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkyl group

2 6 2 6 2 6

, Halo (C—C) alkyl group, (C—C) alkylthio group, halo (CI—C6) alkyl

2 6 1 6

Thio group, (C—C) alkyl carbo group, halo (C—C) alkyl carbo group, (

1 6 1 6

C—C) alkoxycarbonyl group or halo (C—C) alkoxycarbonyl group.

1 6 1 6

), A sulfur atom or a single bond.

1 6 1 6 1 6 ) Alkyl group, (CC) alkyl group, halo (CC) alkenyl group, (CC)

2 10 2 10 2 10 Alkynyl group, halo (C C) alkynyl group, (C C) alkoxycarbonyl (C

2 10 1 6 1

6 1 6

1 6 1 6 1

— C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkoxyloxy group,

6 1 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

Group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C)

2 6 1 6 Killsulfonyl group, /, (C C) alkylsulfoyl group, (C C) alkenylsulfur

1 6 2 6

Phonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino group

1 6

Aromatic 6-membered heterocycle (C C) alkyl group or same or different

1 6

1 6 1 6 2 6

Si group, halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C

2 6 1 6 1 6

) Alkylthio group, (C—C) alkylsulfier group, halo (C—C) alkylsnole

1 6 1 6

Finyl group, (C—C) alkenylthio group, halo (C C) alkenylthio group, (C

2 6 2 6 2

C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (C—C)

1 6 2 6

Sulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6

6

B is

1 6

Mouth (c -c) alkyl group, (c -c) cycloalkyl group or halo (c -c) cycloal

1 6 3 6 3 6

R ³ and R ⁴ together can form a (C—C) alkylene group.

2 6

wear.

1 6 1 6 3 6

Group, halo (c-C) cycloalkyl group, (C-C) alkenyl group, halo (C-C) al

1 6 1 6 1 6 1 6

) Alkylsulfiel (C—C) alkyl group, (C—C) alkylsulfol (C

1 6 1 6 1

C) alkyl group, (C—C) alkoxycarbole (C—C) alkyl group, phenol (C

6 1 6 1 6

1 6

C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C

1 6 1 6 1 6 1

— C) alkoxy group, (C—C) alkenyloxy group, halo (C—C) alkenyloxy

6 2 6 2 6

Si group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyl

1 6 1 6 1 6 Rusulfinyl, halo (C—C) alkylsulfinyl, (C—C) alkenyl

1 6 2 6

Group, halo (C—C) alkenyl dithio group, (C—C) alkenylsulfinyl group, halo (

2 6 2 6

C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C—C)

2 6 1 6 1

) Alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkke

1 6

1 6 1 6 Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) a

1 6 1 6 alkyl group, (c -c) alkoxy group, halo (c 1 -c) alkoxy group, (

6 c 2 -c)

1 6 6 oxy group, halo (C 1 c) alkenyloxy group, (c -c) alkylthio group, halo (

2 6 1 6

c -c) alkylthio group, (c -c) alkylsulfier group, halo (c -c) alkyl

1 6 1 6 1 6 Rusulfinyl group, (c-c) alkenylthio group, halo (c-c) alkenylthio group,

2 6 2 6

(c -c) alkenolinolesulfiel group, halo (c -c) alkenylsulfier group, (

2 6 2 6 C 1 1 C) alkylsulfoel group, halo (C 1 C) alkylsulfonyl group, (C 1 C) al

2 6 1 6 Luamino group or di (c -c) alkylamino group which may be the same or different

1 6

Substituted phenyl (C 1 C) alkynyl groups having 1 to 5 substituents on the ring,

1 6

Ci (C-C) alkyl group, halogen atom which may be the same or different, cyan group, nitro group

1 6

, (C 1 C) alkyl group, halo (C 1 C) alkyl group, (C 1 C) alkoxy group, halo (

1 6 1 6 1 6

C—C) alkoxy group, (C—C) alkenyloxy group, halo (C—C) alkenylo

1 6 2 6 2 6

Xyl group, (C—C) alkylthio group, halo (c -c) alkylthio group, (C—C) al

1 6 1 6 1 6 Kill sulfinyl group, halo (c -c) alkylsulfinyl group, (C—C) alkenyl

1 6 2 6

Thio group, halo (c -c) alkenylthio group, (c -c) alkenylsulfinyl group,

2 6 2 6

(C -c) alkenylsulfinyl group, (c -c) alkylsulfonyl group, halo (

2 6 1 6 C 1

-C) alkylsulfoyl group, (C—C) alkylenolsulfonyl group, halo (C—C) a

6 2 6 2 6 Lucenylsulfonyl group, mono (c -c) alkylamino group or the same or different

1 6

Good di (C—C) alkylamino group with 1-5 substituents on the ring selected

1 6

Substituted phenoxy (c 1 -C 6) alkyl group, phenylthio (c 1 -c 6) alkyl group, identical or

1 6 1 6

1 6 1

-C) alkyl group, (c-c) alkoxy group, halo (c-c) alkoxy group, (c-c)

6 1 6 1 6 2 6 Alkenyloxy group, halo (C 1 c) alkenyloxy group, (c -c) alkylthio

2 6 1 6

Group, halo (c -c) alkylthio group, (c -c) alkylsulfinyl group, halo (C 1

1 6 1 6 1

C) alkylsulfinyl group, (C—C) alkenylthio group, halo (c-c) alkenyl group

2 6 2 6

Nyl group, (C -c) alkylsulfonyl group, halo (C—C) alkylsulfonyl group, (

1 6 1 6 C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C

2 6 2 6 1

6 1 6

1 6

1 6 1 6

-C) alkoxy group, halo (c-c) alkoxy group, (c-c) alkenyloxy group,

1 6 1 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

Group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C)

2 6 1 6 Killsulfonyl group, halo (C C) alkylsulfonyl group, (C—C) alkenylsulfur group

1 6 2 6

Phonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino group

1 6

Substituted phenyl sulfier (C C) alkyl groups having two substituents on the ring, phenyl

1 6

1 6 2 6 2 6 Lucenyloxy group, (C C) alkylthio group, halo (C C) alkylthio group, (C

1 6 1 6 1

—C) alkylsulfinyl group, halo (C—C) alkylsulfinyl group, (C—C)

2 6 2 6

Nyl group, halo (C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group

2 6 1 6

, Halo (C—C) alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C

1 6 2 6

—C) alkenylsulfonyl group, mono (C—C) alkylamino group, or the same or

2 6 1 6

Di (C C) alkylamino groups that may be different Select 1-5 substituents on the ring

1 6

Substituted phenylsulfonyl (C—C) alkyl group, phenylamino (C C)

1 6 alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (C C) alkyl

1 6 1 6 1 6 xy group, (C—C) alkenyloxy group, halo (C—C) alkoxy group, (C

2 6 2 6 1 C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo-

6 1 6 1 6

Group, halo (c -c) alkylsulfier group, (C—C) alkenylthio group, halo (C

1 6 2 6

— C) alkylthio group, (C—C) alksulfyl group, halo (C

2 6 2 6 2

—C) alkylsulfyl group, (C—C) alkylsulfonyl group, halo (C—C)

2 6 2 6 rusulfol group, mono (C—C) alkylamino group

1 6

Nilamino (C C) alkyl group, phenylaminocarbonyl group or the same or different

1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C)

2 6 1 6

(C—C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) al

2 6 2 6

, (C—C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (

2 6 2 6

C—C) alkylsulfonyl group, halo (C—C) alkylsulfonyl group, (C—C)

1 6 1 6 2 6 Lucenylsulfonyl, halo (C—C) alkenylsulfonyl, mono (C—C) al

1 6

And a substituted phenaminocarbo group having 1 to 5 substituents on the ring.

2

Child, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkylcarbohydrate

1 6 1 6 1 6

Group, halo (C—C) alkylcarbonyl group, (C—C) alkoxy (C—C) alkyl

1 6

(In the formula, GH or (c 1 c) alkyl group, halo (c -c) alkyl group, phenyl group,

1 6 1 6

May be different from halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C

1 6

— C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C)

1 6 1 6 1 6 2 6

) Alkenyl, halo (C—C) alkenyl, (C—C) alkynyl, (C—C)

2 6 2 6 3 6 Chloalkyl group, (C—C) alkenyloxy group, halo (c -c) alkenyloxy group

2 6 2 6

, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyl group

1 6 1 6 1 6

Sulfonyloxy group, halo (C—C) alkylsulfonyloxy group, (C—C) alkyl

1 6 1 6 Sulfinyl group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfo

1 6 1 6

Nyl group, halo (C—C) alkylsulfonyl group, (C—C) alkenylthio group, halo (

1 6 2 6

C—C) alkenyl dithio group, (C—C) alkenylsulfier group, halo (C—C) a

2 6 2 6 2 6 Lucenyl sulfier group, (C—C) alkenylsulfonyl group, halo (C—C) alkene

2 6 2 6 Nylsulfonyl, mono (C—C) alkylamino, di (C

1 6 1

—C) alkylamino group, (C—C) alkylsulfonylamino group, halo (C—C) al

6 1 6 1 6 Killsulfonylamino group, (C—C) alkylcarbonyl group, halo (C—C) alkyl

1 6 1 6 Carbonyl group, (C 1 C) alkyloxycarbonyl group, phenyl group, the same or different

1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C)

1 6 1 6 alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkyl

1 6 1 6 1 6 Ruthio group, halo (C—C) alkylthio group, (C—C) alkylsulfinyl group, halo

1 6 1 6

(C—C 1) alkylsulfinyl group, (C—C 1) alkylsulfonyl group or halo (C 1

1 6 1 6 1

C) Alkylsulfonyl group power A substituted phenol group having 1 to 5 substituents selected

6 A phenoxy group or the same or different, a halogen atom, a cyano group, a nitro group, a (c-c) alkyl group, a halo (c-c) alkyl group, a (c-c) alkoxy group, a halo (C

1 6 1 6 1 6 1

-C) alkoxy group, (c -c) alkylthio group, halo (c -c) alkylthio group, (C

6 1 6 1 6

-C) alkylsulfinyl group, halo (c-c) alkylsulfinyl group, (C—C)

1 6

1 6 1

-C) alkyl group, (c -c) alkoxy group, halo (c -c) alkoxy group, (C 1 C)

2 6 1 6

Group, halo (c -c) alkylthio group, (c -c) alkylsulfinyl group, halo (C 1

2 6 2 6

Nyl group, (c -c) alkylsulfonyl group, halo (c -c) alkylsulfonyl group, (

1 6 1 6

c -c) alkenylsulfonyl, halo (C -C) alkenylsulfonyl, mono (C

2 6 2 6 1

6 1 6

1 6 3 6 1

6 1

-C) alkyl group, halo (c -c) alkyl group, (c -c) alkoxy group, halo (c -c

6 1 6 1 6 1

) Alkoxy group, (C—C) alkenyloxy group, halo (C—C) alkenyloxy group

6 2 6 2 6

, (C 1 c) alkylthio group, halo (c -c) alkylthio group, (c -c) alkyls

1 6 1 6 1 6

Rufinyl group, halo (c -c) alkylsulfier group, (c -c) alkenylthio group

1 6 2 6

, Halo (c -c) alkenylthio group, (c -c) alkenylsulfinyl group, halo (C

2 6 2 6 2

-C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C—C)

1 6 (C 1 -C 6) alkylamino group substituted phenyl having 1 to 5 selected substituents on the ring

1 6

-Lu (c -c) alkyl group, pyridyl (c -c) alkyl group or the same or different

1 6 1 6

1 6 1 6 2 6 oxy group, halo (c -c) alkenyloxy group, (c -c) alkylthio group, halo (

2 6 1 6 C 1

-C) alkylthio group, (C—C) alkylsulfinyl group, halo (c -c) alkyl

2 6 2 6 C

-C) alkenylsulfinyl group, halo (

6 c 2 -c) alkenylsulfinyl group, (

2 6 C 1

C) alkylsulfonyl group, halo (c-c) alkylsulfonyl group, (C—C) alkke

6 1 6 2 6 Nylsulfonyl group, halo (C C) alkenylsulfonyl group, mono (C C) alkyl

2 6 16 Amino group or di (C—C) alkylamino group which may be the same or different A substituted pyridyl (C C) alkyl group having 1 to 4 selected substituents on the ring. Or

(Wherein R ³ , R ⁴ and W are the same as above, and R ⁷ and R ° may be the same or different, a hydrogen atom, a (C—C 1) alkyl group, a halo (C 1 -C 6) alkyl group, (C—C) cycloalkyl

1 6 1 6 3 6

A group or a halo (c 1 -c 3) cycloalkyl group.

3 6

-C) alkyl group, halo (c -c) alkyl group, (c -c) alkoxy group, halo (C

1 6 1 6 1 6 1

C) alkoxy group, (C C) alkenyl group, halo (C C) alkenyl group, (C C)

2 6 1 6 1 6

Group, (C—C) alkylsulfo-loxy group, halo (C—C) alkylsulfo-luo group

1 6 1 6

A xy group, a (C 1 c) alkylsulfyl group, a halo (c-c) alkylsulfiel group,

1 6 1 6

(C 1 C) alkylsulfonyl group, halo (C 1 C) alkylsulfonyl group, (C 1 C)

2 6 2 6

-Luyl group, halo (C—C) alkulsulfyl group, (C—C) alkenylsulfonyl

2 6 2 6

2 6 1 6

Or a di (C—C) alkylamino group, which may be different, (C—C) alkylsulfuryl

1 6 1 6

Mino group, halo (C—C) alkylsulfonylamino group, (C—C) alkyl carbonyl group

1 6 1 6

, Halo (C—C) alkylcarbonyl group, (C—C) alkyloxycarbonyl group,

1 6 1 6

1 6 alkyl, halo (C—C) alkyl, (C—C) alkoxy, halo (C—C) alkyl

1 6 1 6

1 6

1 6 1 6 1 6

) Alkoxy, halo (C—C) alkoxy, (C—C) alkylthio, halo (C 1

1 6 1 6 1

C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) alkyl group

6 1 6 1 6

Rufinyl group, (C—C) alkylsulfonyl group, or halo (C—C) alkylsulfoni

1 6 alkyl, halo (C—C) alkyl, (C—C) alkoxy, halo (C—C) alkyl

2 6 2 6 1

C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfini

6 1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C

1 6 2 6

—C) alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) al

2 6 2 6 2 6 Kenylsulfuryl group, (C—C) alkylsulfol group, halo (c-c) alkylsulfonyl group, (C—C) alkylsulfol group, halo (C—C) alkylsulfol-

2 6 2 6

R is a hydrogen atom, (C C) alkyl group, halo (C C) alkyl group, (C C) cyclo

1 1 6 3 6 Alkyl group, halo (C—C) cycloalkyl group, (C—C) alkenyl group, halo (C

3 6 2 10 2

C) alkyl group, (C—C) alkyl group, halo (C—C) alkyl group, (C

10 2 10 2 10 1

C) alkoxycarbol (C—C) alkyl group, phenol (C—C) alkyl group or

6 1 6 1 6

1 6 1 6 1 6

, (C—C) alkenyloxy group, halo (C—C) alkenyloxy group, (C—C)

1 6 1 6

Halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C

1 6 2 6 2 6

) Alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyl group

1 6 1 6

Nyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group

2 6 2 6

A mono (C—C) alkylamino group or the same or different di (C—C) al

1 6 represents an alkyl group. } Acetonitrile derivative represented by:

[2] General formula (I 1)

{Wherein Q ¹ is a (C—C) alkyl group, a halo (C—C) alkyl group, (C—C Kill group, halo (c -c) cycloalkyl group, phenol group, same or different

3 6

1 6 1 6

C—C) alkoxy, halo (C—C) alkoxy, (C—C) alkenyl, halo (

1 6 1 6 2 6

C C) alkyl group, (C C) alkyl group, (C C) cycloalkyl group, (C

2 6 2 6 3 6 2

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkyl group

1 6 1 6

Mouth (C—C) alkyl sulfo-loxy group, (C—C) alkyl sulfier group, halo (

1 6 1 6

C—C) alkylsulfier group, (C—C) alkylsulfonyl group, halo (C—C)

2 6 2 6

O group, (C—C) alkenylsulfuryl group, halo (C—C) alkulsulfyl group

2 6 2 6

Group, (C—C) alkenyl sulfonyl group, halo (C—C) alkenyl sulfonyl group,

2 6 2 6

(C—C) alkylamino group, same or different di (C—C) alkylamino group

1 6 1 6

Group, (C—C) alkylsulfonylamino, halo (C—C) alkylsulfonylamino

1 6 1 6

Group, (C C) alkylcarbonyl group, halo (C C) alkylcarbonyl group, (C

1 6 1 6 1

6

1 6 1 6 1 6

) Alkoxy group, halo (c—C) alkoxy group, (C—C) alkylthio group, halo (C

1 6 1 6 1

C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) alkyls

6 1 6 1 6

Rufinyl group, (c—C 1) alkylsulfonyl group or halo (C—C 1) alkylsulfone

1 6

, Halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group,

1 6 1 6 1 6

(C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo group

1 6 1 6 1 6

Finyl group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl

1 6 1 6

1 6

Group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo

1 6 2 6 2 6 2

— C)) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

-Luoxy group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi group

1 6 1 6

Group, (C—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (

1 6 1 6

C—C) alkenylthio group, halo (C—C) alkthio group, (C—C) alkenyl group

2 6 2 6 2 6

Rusulfier group, halo (C—C) alkenylsulfier group, (C—C) alkenyl

2 6 2 6

Sulfonyl group, halo (C—C) alkylenosulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkyl carbonyl

1 6 1 6

Ball group, halo (C—C) alkylcarbonyl group, (C—C) alkyloxycarboxyl

1 6 1 6

6 1 6 1 6 1

) Alkoxy, (C—C) alkylthio, halo (C—C) alkylthio, (C 1

6 1 6 1 6 1

C) alkylsulfinyl group, halo (C—C) alkylsulfinyl group, (C—C) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio, (C 1 C) alkylsulfinyl, halo (C—C)

1 6

, (C -c) alkyl group, halo (c -c) alkyl group, (c -c) alkoxy group, halo (

1 6 1 6 1 6

c -c) alkoxy group, (c -c) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

-C) alkyl group, (c-c) cycloalkyl group, (c-c) alkenyloxy group,

6 3 6 2 6 Halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

-Luoxy group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi group

1 6 1 6

Group, (C—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (

1 6 1 6

C—C) alkthio group, halo (C—C) alkthio group, (C—C) alkyl group

2 6 2 6 2 6

Rusulfyl group, halo (C—C) alkulsulfyl group, (C—C) alkell

2 6 2 6

Sulfol group, halo (C—C) alkaryl sulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkyl carbo group, (C C) alkyloxy carbo-

1 6 1 6

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

Selected from 1 6 1 6 rusulfonyl group

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C) a

2 6 2 6 1 6

) Alkylthio, halo (C—C) alkylthio, (C—C) alkylsulfonyl

1 6 1 6 Xyl group, halo (c—C) alkylsulfuroxy group, (C—C) alkylsulfi-

1 6 1 6

Group, halo (c -C) alkylsulfiel group, (C—C) alkylsulfol group,

1 6 1 6

(C—C) alkylsulfol group, (C—C) alkylthio group, halo (C—C) a

2 6 2 6

Rufinyl group, (C—C) alkenylsulfonyl group, halo (c -c) alkenylsulfo

2 6 2 6

1 6 1 6

-Luamino group, (C—C) alkylcarbonyl group, halo (C—C) alkylcarbonyl

1 6 1 6

1 6

1 6 1 6

(C—C) alkoxy group, halo (c-c) alkoxy group, (C-C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C-C) alkylsulfier group, halo (C—C)

1 6

6

C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C −

1 6 1 6 1 6 2

C) alkyloxy group, halo (c-c) alkoxy group, (C—C) alkylthio

6 2 6 1 6

Group, halo (c -c) alkylthio group, (C—C) alkylsulfier group, halo (C

1 6 1 6 1

—C) alkylsulfinyl group, (C 1 C) alkylthio group, halo (C—C) alkke

2 6 2 6

Ynyl group, (C—C) alkylsulfoyl group, halo (C—C) alkylsulfonyl group, (

2 6 2 6 1

6 1 6

R is a hydrogen atom, (C C) alkyl group, halo (C C) alkyl group, (C C) cyclo

3 6 2 10 2

C) alkyl group, (C—C) alkyl group, halo (C—C) alkyl group, (C

10 2 10 2 10 1

C) alkoxycarbol (C—C) alkyl group, phenol (C—C) alkyl group or

6 1 6 1 6

1 6 1 6 1 6

, (C—C) alkenyloxy, halo (C—C) alkenyloxy, (C—C)

1 6 1 6

Halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C

1 6 2 6 2 6

) Alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyl group

2 6 2 6

Rusulfinyl group, (C—C) alkylsulfonyl group, halo (C—C) alkylsulfo group

1 6 1 6

Nyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group

2 6 2 6

A mono (C—C) alkylamino group or the same or different di (C—C) al

1 6 represents an alkyl group.

R ¹ is a hydrogen atom, (CC) alkyl group, halo (CC) alkyl group, (CC) al

1 6 2 6 2 6

, (C—C) alkynyl group, halo (C—C) alkynyl group, (C—C) alkylcarbo

2 6 2 6 1 6

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C)

1 6 1

) Alkyl group, (C C) alkoxy group or halo (C C) alkoxy group

6 1 6 1 6

A substituted phenylcarbonyl group having 1 to 5 substituents, (C C) alkoxycal

1 6

A bonyl group or a halo (C C) alkoxycarbonyl group is shown.

1 6

1 6 1 -c) alkyl group, (c-c) cycloalkyl group or halo (c-c) cycloalkyl group

6 3 6 3 6

R ³ and R ⁴ may be joined together to form a (C—C) alkylene group.

2 6

1 6 1 6 3 6

Group, halo (C C) cycloalkyl group, (C C) alkenyl group, halo (C C) al

2 10 2 10 1 6 Xyl (C C) alkyl group, (C C) alkylthio (C C) alkyl group, (C C

1 6 1 6 1 6 1 6

) Alkylsulfinyl (c 1 -c) alkyl groups, (

6 C 1—C) alkylsulfonyl (

6 C 1 c) alkyl group, (c -c) alkoxycarbonyl (c -c) alkyl group, phenyl (

6 1 6 1 6 C

1 6

C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C

1 6 1 6 1 6 1

— C) alkoxy group, (C—C) alkenyloxy group, halo (C—C) alkenyloxy

6 2 6 2 6

Si group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyl

1 6 1 6 1 6 Rusulfinyl, halo (C—C) alkylsulfinyl, (C—C) alkenyl

1 6 2 6

Group, halo (C—C) alkenyl dithio group, (C—C) alkenylsulfinyl group, halo (

2 6 2 6

C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C—C)

2 6 1 6 1

) Alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkke

1 6

1 6 1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) a

1 6 1 6 alkyl, (C—C) alkoxy, halo (C—C) alkoxy, (C—C) alkenyl

2 6 1 6

C—C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) alkyl

2 6 2 6

(C—C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (C

2 6 2 6 1 C) alkylsulfonyl group, halo (C C) alkylsulfonyl group, (C C) al

1 6

, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (

1 6 1 6 1 6

C—C) alkoxy, (C—C) alkenyloxy, halo (C—C) alkenyl

1 6 2 6 2 6

Xyl, (C—C) alkylthio, halo (C—C) alkylthio, (C—C) al

1 6 2 6

Thio, halo (C—C) alkenylthio, (C—C) alkenylsulfinyl,

2 6 2 6

(C—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C

2 6 1 6 1

—C) alkylsulfonyl group, (C—C) alkenylsulfonyl group, halo (C—C) a

1 6

Good di (C—C) alkylamino group with 1-5 substituents on the ring selected

1 6

1 6 1 6

1 6 1

— C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C)

2 6 1 6

Group, halo (C C) alkylthio group, (C C) alkylsulfinyl group, halo (C

1 6 1 6 1

C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C) alkenyl group

2 6 2 6

Nyl group, (C—C 1) alkylsulfonyl group, halo (C—C 1) alkylsulfonyl group, (

1 6 1 6

C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C

2 6 2 6 1

6 1 6

1 6

1 6 1 6

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkenyloxy group,

1 6 1 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

Group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C)

2 6 2 6 2 6 Luke-Lulsulfininole group, halo (c—C) alkenolinole norefier group, (C—C) anole

1 6 2 6

Hole group, halo (c -c) alkaryl sulfol group, mono (C—C) alkylamino group

1 6

1 6 1 6 1 1 C) alkylsulfinyl group, halo (C 1 C) alkylsulfinyl group, (C 1 C)

2 6 2 6

Nyl group, halo (C—C) alkenolinolesulfier group, (c -c) alkylsulfonyl group

2 6 1 6

, Halo (C 1 C) alkylsulfonyl group, (C 1 C) alkenylsulfonyl group, halo (C

1 6 2 6

—C) alkenylsulfonyl group, mono (C—C) alkylamino group, or the same or

2 6 1 6

1 6

Substituted phenylsulfonyl (C—C) alkyl group, phenylamino (C—C)

1 6 alkyl, halo (C—C) alkyl, (C—C) alkoxy, halo (C—C) alkyl

2 6 2 6 1

C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfini

6 1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C 1 C) alkenylthio group, halo (C

1 6 2 6

—C) alkenyl thio group, (C—C) alkenyl sulfinyl group, halo (C

2 6 2 6 2 1 C) alkenylsulfinyl group, (C 1 C) alkylsulfonyl group, halo (C 1 C)

1 6

A halogen atom, cyano group, nitro group, (C 1, halo (

1 C) alkyl group

6 C 1— C 6) An alkyl group, a (c 1 -c) alkoxy group, a halo (c 1 -c) alkoxy group, (

1 6 6 c 2 -c)

6

-Luoxy group, halo (c -c) alkoxy-oxy group, (C—C) alkylthio group, halo

2 6 1 6

(C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) al

2 6 2 6

, (C—C) alkulsulfyl group, halo (C—C) alkulsulfyl group, (

2 6 2 6

C—C) alkylsulfol group, halo (C—C) alkylsulfonyl group, (C—C)

1 6

And a substituted phenaminocarbo group having 1 to 5 substituents on the ring.

2

Child, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkylcarbohydrate

1 6 1 6 1 6

Group, halo (C—C) alkylcarbonyl group, (C—C) alkoxy (C—C) alkyl

1 6

It can also form 5- to 8-membered rings which can be interrupted by atoms, sulfur atoms or nitrogen atoms. ). }

Acetonitrile derivative represented by:

[3] Q ¹ is (C—C) alkyl group, halo (C—C) alkyl group, (C—C) cycloalkyl

1 6 1 6 3 6 group, halo (C C) cycloalkyl group, phenol group, halogen which may be the same or different

3 6

Atoms, (C C) alkyl groups, halo (C C) alkyl groups, (C C) alkoxy groups,

1 6 1 6 1 6 halo (C C) alkoxy group, phenol group, halogen atom which may be the same or different,

1 6

Ciano group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C—C)

1 6 1 6 1 6 Lucoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C—C) group

1 6 1 6 1 6 Alkylthio group, (C—C) alkylsulfier group, halo (C—C) alkylsulfur group

1 6 1 6

A reel group, a (C—C) alkylsulfol group or a halo (C—C) alkylsulfol group

A substituted phenyl group having 1 to 5 substituents selected from 1 6 1 6 groups, a phenoxy group, or a halogen atom, a cyan group, a nitro group, a (C—C) alkyl group, which may be the same or different,

1 6

Halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (

1 6 1 6 1 6

C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo group

1 6 1 6 1 6 Fier group, halo (c -c) alkylsulfier group, (C—C) alkylsulfol

1 6 1 6

Group or halo (C C) alkylsulfol group with 1 to 5 substituents selected

1 6

Substituted phenyl groups with 1 to 5 substituents selected, phenyl (C—C) alkyl groups, halogen atoms which may be the same or different, (C—C) alkyl

1 6 1 6 group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy

1 6 1 6 1 6 group, phenol group, halogen atom, cyan group, nitro group, (C-C) alkyl group, halo (CC) alkyl group, (CC) alkoxy group, which may be the same or different, Halo (CC)

6 1 6 1 6 1 6 alkoxy group, (c -C) alkylthio group, halo (c -c) alkylthio group, (c -c

1 6 1 6 1 6

) Alkylsulfier group, halo (c -c) alkylsulfier group, (C—C) alkyl

1 to 6 selected from 1 6 1 6 rusulfol group or halo (C C) alkylsulfol group

1 6

1 6 1 6

-c) alkoxy group, halo (c-c) alkoxy group, (c-c) alkylthio group, halo

1 6 1 6 1 6

(c -c) alkylthio group, (C—C) alkylsulfier group, halo (c -c) al

1 6 1 6 1 6 Killsulfier group, (C—C) alkylsulfol group or halo (c -c) alkyls

1 6 1 6

Substituted phenoxy group having 1 to 5 substituents selected. Substituted phenyl (C C) alkyl group having 1 to 5 substituents on the ring, phenoxy (

1 6

C—C) alkyl group, halogen atom which may be the same or different, (C—C) alkyl

1 6 1 6

Group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group

1 6 1 6 1 6

, Phenol groups, halogen atoms which may be the same or different, cyan groups, nitro groups, (C—C

1 6

) Alkyl, halo (C—C) alkyl, (C—C) alkoxy, halo (C—C)

1 to 6 selected from 1 6 1 6 rusulfonyl group or halo (C C) alkylsulfonyl group

1 6

A substituted phenyl group having a substituent, a phenoxy group, or a halogen atom, cyan group, nitro group, (C—C 1) alkyl group, halo (C—C 1) alkyl group, which may be the same or different, (C

1 6 1 6

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group, halo

1 6 1 6 1 6

(C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) al

1 6 1 6 1 6 Killsulfier group, (C—C) alkylsulfol group or halo (c -c) alkyls

1 6 1 6

A substituted phenoxy group having 1 to 5 substituents selected a substituted phenoxy (C 1 -C 6) alkyl group having 1 to 5 substituents on the ring, phenyl

1 6

Mino group, halogen atom which may be the same or different, (c -c) alkyl group, halo (c -c

1 6 1

) Alkyl group, (c -c) alkoxy group, halo (c -c) alkoxy group, phenyl group,

6 1 6 1 6

One or different halogen atoms, cyan groups, nitro groups, (C—C) alkyl groups,

1 6

Mouth (c -c) alkyl group, (c -c) alkoxy group, halo (c -c) alkoxy group, (C

1 6 1 6 1 6 1

-C) alkylthio, halo (c-c) alkylthio, (C-C) alkylsulfi

6 1 6 1 6

Nyl group, halo (C C) alkylsulfinyl group, (C C) alkylsulfonyl group,

1 6 1 6

Is a group having 1 to 5 substituents selected from a halo (C C) alkylsulfonyl group

1 6

A substituted phenyl group, a phenoxy group, or a halogen atom, cyan group, nitro group, (c -c) alkyl group, halo (c -c) alkyl group, (C—C) alkoxy group which may be the same or different

1 6 1 6 1 6 Si group, halo (c -c) alkoxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6 1 6 Kirthio group, (C—C) alkyl sulfier group, halo (c -c) alkyl sulfi-

1 6 1 6

Group, (C C) alkylsulfol group or halo (C C) alkylsulfonyl group

1 6 1 6

A substituted phenoxy group having 1 to 5 substituents selected from the above, a substituted phenylamino group having 1 to 5 substituents selected on the ring, a pyridyl group, or a halogen atom which may be the same or different, Ciano group, nitro group, (C—C) alkyl group, halo (C—C) al

1 6 1 6 2 6oxy group, halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C

2 6 1 6 1

—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) alkyl

6 1 6 1 6 Sulfiel group, (C—C) alkthio group, halo (C—C) alkthio group, (C

2 6 2 6

—C) alkulsulfyl group, halo (C—C) alkulsulfyl group, (C

2 6 2 6 1

C) alkylsulfol group, halo (C—C) alkylsulfol group, (C—C) alkke

6 1 6 2 6 Nylsulfol group, halo (C—C) alkylsulfol group, mono (C—C) alkyl

1 6

A substituted pyridyl group having one or more substituents,

R is a hydrogen atom, (C C) alkyl group, halo (C C) alkyl group, (C C) cyclo

1 6 1 6 3 6 An alkyl group or a halo (C 1 -C 6) cycloalkyl group, R ¹ is a hydrogen atom, (C 1 -C 6)

3 6 1 6 represents an alkyl group, a (C 1 -C 6) alkyl carbonyl group or a phenol group, R ³

1 6

And R ⁴ may be the same or different and each represents a hydrogen atom or a (C—C) alkyl group,

1 6

R ⁵ is (C—C 1) alkyl group, halo (C—C 1) alkyl group, (C—C 1) cycloalkyl

1 6 1 6 3 6 group, halo (C C) cycloalkyl group, (C C) alkenyl group, halo (C C) al

3 6 2 10 2 10 Kenyl group, (C—C) alkynyl group, halo (C—C) alkynyl group, (C—C) alkoxy

2 10 2 10 1 6 Xyl (C C) alkyl group, (C C) alkylthio (C C) alkyl group, (C C

1 6 1 6 1 6 1 6

) Alkylsulfinyl (C—C) alkyl group, (C—C) alkylsulfonyl (C

1 6 1 6 1

C) alkyl group, (C—C) alkoxycarbonyl (C—C) alkyl group, phenyl (C

6 1 6 1 6

1 6

C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group or halo (

1 6 1 6 1 6

(C C) Substituted phenyl having 1 to 5 substituents selected from alkoxy groups on the ring

1 6

(C—C) alkenyl group, phenyl (C—C) alkynyl group, the same or different

1 6 1 6

1 6 1 6 group, (C—C) alkoxy group or halo (C—C) alkoxy group force 1 to 5 selected

1 6 1 6

Substituted phenyl (C C) alkynyl group, phenoxy (C C

1 6 1 6

) Alkyl group, halogen atom which may be the same or different, cyan group, nitro group, (C—C

1 6

) Alkyl, halo (C—C) alkyl, (C—C) alkoxy or halo (C—C)

1 6 1 6 1 6

) Alkoxy group substitution Substitution with 1 to 5 substituents on the ring selected:

C) an alkyl group, a phenaminocarbo group or a halo which may be the same or different

6

1 6 1 6

—C) alkoxy group or halo (C—C) alkoxy group power 1 to 5 substitutions selected

1 6 1 6

A substituted phenaminocarbo group having a group on the ring;

W is an oxygen atom, sulfur atom, or —NR ⁹ (wherein R ⁹ is a hydrogen atom, (C—C) alkyl)

6 or a (C—C) alkoxy (C—C) alkyl group, or together with

1 6 1 6

Thus, a 5- to 8-membered ring which may be interrupted by an oxygen atom, a sulfur atom or a nitrogen atom can be formed. 3. The acetonitrile derivative according to claim 2, wherein:

[4] Q ¹ is a (C—C) cycloalkyl group, a halo (C—C) cycloalkyl group, a phenol group, One or different halogen atom, (C—C) alkyl group, halo (C—C) alkyl

1 6 1 6 group, (C C) alkoxy group or halo (C C) alkoxy group selected 1-5

1 6 1 6

Substituted phenyl groups, phenyl (C C) alkyl groups, the same or different

1 6

Halogen atom, (C—C) alkyl group, halo (C—C) alkyl group, (C

1 6 1 6 1

C) alkoxy group or halo (C C) alkoxy group force 1-5 substituents selected

6 1 6

A substituted fur (C C) alkyl group, a phenoxy (C C) alkyl group on the ring,

1 6 1 6

Halogen atoms that may be the same or different, (C—C) alkyl groups, halo (C—C) al

1 6 1 6 Kill group, (C C) alkoxy group or halo (C C) alkoxy group selected 1 to

1 6 1 6

Substituted phenoxy (C C) alkyl group having 5 substituents, phenolamino group, identical

1 6

Or a halogen atom which may be different, (C—C) alkyl group, halo (C—C) alkyl

1 6 1 6 groups, (C C) alkoxy groups, halo (C C) alkoxy groups 1 to 5 selected

1 6 1 6

A substituted phenylamino group having a substituent on the ring, a pyridyl group, or a halogen atom which may be the same or different, a (C—C) alkyl group, a halo (C—C) alkyl group, a (C—C) a

1 6 1 6 1 6 having one or more substituents selected from a alkoxy group or a halo (C—C) alkoxy group

1 6

Represents a substituted pyridyl group,

R represents a hydrogen atom or a (C—C) alkyl group, R ¹ represents a hydrogen atom or a (C—C) alkyl group

1 6 1 6 represents a kill group, R ³ and R ⁴ represent a hydrogen atom, R ⁵ represents a (C—C) alkyl group, halo (C

1 6 1

C) alkyl group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C—C)

6 2 10 2 10 2 10

) Alkynyl group, halo (C C) alkynyl group, (C C) alkoxy (C C) al

2 10 1 6 1 6 Kill group, (C—C) alkylthio (C—C) alkyl group, (C—C) alkylsulfi

1 6 1 6 1 6

Nyl (C—C) alkyl group, (C—C) alkylsulfonyl (C—C) alkyl group,

1 6 1 6 1 6

A (C—C) alkenyl group, halogen atoms which may be the same or different, (C—C)

1 6 1 6 alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group or halo (C—C)

1 6 1 6 1 6 Substituted phenyl (C C C) having 1 to 5 substituents selected from alkoxy groups on the ring

1 6

) Alkenyl group, phenyl (C C) alkynyl group, halogen which may be the same or different

1 6

Atom, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group

1 6 1 6 1 6

Or a halo (C C) alkoxy group selected from those having 1 to 5 selected substituents on the ring

1 6

Substituted phenyl (C—C) alkynyl group, phenoxy (C—C) alkyl group, the same or different

1 6 1 6 Halogen atom, (CC) alkyl group, halo (CC) alkyl group, (C

1 6 1 6 1

C) alkoxy group or halo (C 1 -C 6) alkoxy group force 1-5 substituents selected

6 1 6

A substituted phenoxy (c-c) alkyl group, phenolaminocarbol group having on the ring, or

1 6

Halogen atom, (c -c) alkyl group, halo (C—C) a which may be the same or different

1 6 1 6 Alkyl group, (C—C) alkoxy group or halo (C—C) alkoxy group selected 1

1 6 1 6

Represents a substituted phenylaminocarbol group having ~ 5 substituents on the ring;

W is an oxygen atom, sulfur atom, or —NR ⁹ — (wherein R ⁹ is a (C—C) alkyl group or (C

1 6 1

— C) alkoxy (CC) alkyl group, and R ⁹ together with R ⁵ is pyrrole

6 1 6

Rings, pyrazoline rings, pyrazole rings, imidazole rings, triazole rings, tetrazole rings, piperazine rings, piperidine rings, morpholine rings, and thiomorpholine rings can also be formed. Acetonitrile derivative according to any one of claims 2 and 3, wherein:

Formula (I 2)

1 6 1 6 3 6

Kill group, halo (C C) cycloalkyl group, phenyl group, the same or different

3 6

1 6 1 6

C—C) alkoxy, halo (C—C) alkoxy, (C—C) alkenyl, halo (

1 6 1 6 2 6

C C) alkenyl group, (C C) alkynyl group, (C C) cycloalkyl group, (C

2 6 2 6 3 6 2

—C) alkenyloxy group, halo (C—C) alkenyloxy group, (C—C) alkynole

6 2 6 1 6 thio group, halo (C—C) alkylthio group, (C—C) alkylsulfonyloxy group,

1 6 1 6

(C—C) alkylsulfonyloxy group, (C—C) alkylsulfinyl group, halo (

1 6 1 6

CC) alkylsulfinyl group, (CC) alkylsulfonyl group, halo (C—C) Alkylsulfol group, (C—C) alkylthio group, halo (C—C) alkenyl group

2 6 2 6

O group, (C—C) alkenylsulfuryl group, halo (C—C) alkulsulfyl group

2 6 2 6

Group, (C—C) alkenyl sulfonyl group, halo (C—C) alkenyl sulfonyl group,

2 6 2 6

(C—C) alkylamino group, same or different di (C—C) alkylamino group

1 6 1 6

Group, (C—C) alkylsulfonylamino, halo (C—C) alkylsulfonylamino

1 6 1 6

Group, (C C) alkylcarbonyl group, halo (C C) alkylcarbonyl group, (C

1 6 1 6 1

6

1 6 1 6 1 6

) Alkoxy group, halo (c—C) alkoxy group, (C—C) alkylthio group, halo (C

1 6 1 6 1

C) alkylthio, (C—C) alkylsulfinyl, halo (C—C) alkyls

6 1 6 1 6

Rufinyl group, (c—C 1) alkylsulfonyl group or halo (C—C 1) alkylsulfone

1 6

, Halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group,

1 6 1 6 1 6

(C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo group

1 6 1 6 1 6

Finyl group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl

1 6 1 6

1 6

Group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo

1 6 1 6 1 6

(C C) alkoxy group, (C C) alkenyl group, halo (C C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C) alkenyl group

2 6 2 6 2 6

Rusulfinyl group, halo (C—C) alkenylsulfinyl group, (C—C) alkenyl

2 6 2 6 Sulfol group, halo (c-c) alkylsulfol group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkyl carbo group, (C C) alkyloxy carbo-

1 6 1 6

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

1 6

, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (

1 6 1 6 1 6

C—C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkynyl group, (C—C) cycloalkyl group, (C—C) alkenyloxy group,

6 3 6 2 6

Halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

2 6 2 6

Sulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Ball group, halo (C C) alkylcarbol group, (C—C) alkyloxycarboxyl

1 6 1 6

6 1 6 1 6 1

) Alkoxy group, (c—C 1) alkylthio group, halo (C—C 1) alkylthio group, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (Cc) alkylsulfier group, (c-c) al

1 6

1 6 1 6

, (C—C) alkoxy group, halo (c-c) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C C)

Selected from 1 6 1 6 norsulfonyl group

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C) a

2 6 2 6 3 6 group, (C—C) alkenyloxy group, halo (C—C) alkoxy group, (C—C

2 6 2 6 1 6

) Alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo-luo

1 6 1 6

Xyl group, halo (C—C) alkylsulfonyloxy group, (C—C) alkylsulfinyl

1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl group,

1 6 1 6

(C—C) alkylsulfonyl group, (C—C) alkylthio group, halo (C—C) a

2 6 2 6

Rufinyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfo group

1 6 1 6 Nylamino group, (C—C) alkylcarbonyl group, halo (C C) alkylcarbonyl

1 6 1 6 Group, (c -c) alkyloxycarbol group, phenol group, the same or different

1 6

Halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C C) alkyl group

1 6 1 6

, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group,

1 6 1 6 1 6

Halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C)

16 alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C)

1 to 6 selected from 1 6 1 6 rusulfonyl group or halo (C C) alkylsulfonyl group

1 6

C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C −

1 6 1 6 1 6 2

C) alkenyloxy group, halo (c-c) alkenyloxy group, (C—C) alkylthio group

6 2 6 1 6

Group, halo (c -c) alkylthio group, (c -c) alkylsulfinyl group, halo (C

1 6 1 6 1

-C) alkylsulfinyl group, (C-C) alkenylthio group, halo (c-c) alkke

6 2 6 2 6 Diruthio, (C—C) alkenylsulfinyl, halo (c -c) alkenylsulfur

2 6 2 6

Ynyl group, (c -c) alkylsulfonyl group, halo (c -c) alkylsulfonyl group, (

1 6 1 6

c -c) alkenylsulfonyl group, halo (c -c) alkenylsulfonyl group, mono (C

2 6 2 6 1

6 1 6

Q ² is a (C 1 -C 6) alkyl group, a halo (C 1 -C 6) alkyl group, a phenyl group, the same or different

1 6 1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C C)

1 6 1 6 2 6

-Luyl group, halo (C—C) alkyl group, (C—C) alkyl group, (C—C) cycloa

2 6 2 6 3 6 Alkyl group, (c—C) alkoxy group, halo (C—C) alkoxy group, (C

2 6 2 6 1

— C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfo-

6 1 6 1 6

Ruoxy group, halo (C—C) alkylsulfo-loxy group, (C—C) alkylsulfur group

1 6 1 6

Shield group, halo (C—C) alkylsulfier group, (C—C) alkylsulfol group

1 6 1 6

, Halo (C—C) alkylsulfol group, (C—C) alkylthio group, halo (C—C

1 6 2 6 2 6

) Alkthio group, (C—C) alksulfyl group, halo (C—C) alkenyl group

2 6 2 6 Rusulfyl group, (C—C) alkaryl sulfonyl group, halo (C—C) alkyl group

2 6 2 6

1 6 1 6 alkylamino group, (C—C) alkylsulfo-lumino group, halo (C—C) alkyls

1 6 1 6

Ruphoro-Lamino group, (C—C) alkylcarbole group, halo (C—C) alkylcarbo group

1 6 1 6

-Group, (C-C) alkyloxycarbol group, phenol group, the same or different

1 6

1 6 1 6 kill group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkyl group

1 6 1 6 1 6o group, halo (C—C) alkylthio group, (C—C) alkylsulfier group, halo (C

1 6 1 6 1

—C) alkylsulfier group, (C—C) alkylsulfonyl group or halo (C—C)

6 1 6 1 6 Alkylsulfol group selected Substitued furol group having 1 to 5 substituents, phenoxy group, halogen atom, cyan group, nitro group, which may be the same or different, ( C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy group, halo (C—C)

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

1 6

1 6 1 6 2 6

-Luoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group, halo

2 6 1 6

(C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) al

2 6 2 6 , (C—C) alkulsulfyl group, halo (C—C) alkulsulfyl group, (

2 6 2 6

C—C) alkylsulfol group, halo (C—C) alkylsulfonyl group, (C—C)

1 6

R is a hydrogen atom, (C C) alkyl group, halo (C C) alkyl group, (C C) cyclo

3 6 2 10 2

C) alkyl group, (C—C) alkyl group, halo (C—C) alkyl group, (C

10 2 10 2 10 1

C) alkoxycarbol (C—C) alkyl group, phenol (C—C) alkyl group or

6 1 6 1 6

1 6 1 6 1 6

, (C—C) alkenyloxy, halo (C—C) alkenyloxy, (C—C)

1 6 1 6

Halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C

1 6 2 6 2 6

) Alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) alkenyl group

1 6 1 6

Nyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group

2 6 2 6

A mono (C—C) alkylamino group or the same or different di (C—C) al

1 6 represents an alkyl group.

R ¹ is a hydrogen atom, (CC) alkyl group, halo (CC) alkyl group, (CC) al

1 6 2 6 2 6

, (C—C) alkynyl group, halo (C—C) alkynyl group, (C—C) alkylcarbo

2 6 2 6 1 6

1 6

Halogen atom, nitro group, cyano group, (C—C) alkyl group, halo (C—C)

1 6 1

) Alkyl group, (C C) alkoxy group or halo (C C) alkoxy group

6 1 6 1 6

A substituted phenylcarbonyl group having 1 to 5 substituents, (C C) alkoxycal

1 6 A ball group or a halo (cc) alkoxycarbo group is shown.

1 6

1 6 3 6 1

6 1 C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (C C

6 1 6 1 6 1

) Alkoxy group, (c—C) alkenyloxy group, halo (C—C) alkenyloxy group

6 2 6 2 6

, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyl group

1 6 1 6 1 6

Rufinyl group, halo (C C) alkylsulfinyl group, (C C) alkenylthio group

1 6 2 6

, Halo (C—C) alkenylsulfonyl group, (C—C) alkenylsulfinyl group, halo (C

2 6 2 6 2

—C) alkenylsulfinyl group, (C—C) alkylsulfonyl group, halo (C—C)

1 6

-L (C—C) alkyl group, pyridyl (C—C) alkyl group or the same or different

1 6 1 6

2 6 1 6 1

—C) alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) alkyl

6 1 6 1 6 Sulfinyl group, (c—C) alkenylthio group, halo (C—C) alkenylthio group, (C

2 6 2 6

—C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (C

2 6 2 6 1

C) alkylsulfonyl group, halo (C—C) alkylsulfonyl group, (C—C) alkke

6 1 6 2 6 Nylsulfonyl group, halo (C C) alkenylsulfonyl group, mono (C C) alkyl

1 6

R and R ⁶ may be combined together — X ¹ — X ² — (wherein X ¹ and X ² may be the same or different, and may be a carbonyl group, a (C—C) alkylene group, or the same or different. Halogen

1 6

1 6 1 6

-Group, halogen atom, cyan group, nitro group, (C—C) al, which may be the same or different

1 6 Kill group, halo (C—C) alkyl group, (C—C) alkoxy group or halo (C—C) al

1 6 1 6 1 6 Coxyl group power Substituted phenyl group having 1 to 5 substituents, pyridyl group or halogen atom, cyan group, nitro group, (C—C) alkyl, which may be the same or different

1 6

I'll do it for you. }

Acetonitrile derivative represented by:

[6] Q ¹ may be a phenyl group or a halogen atom, nitro group, cyano group, (CC) alkyl group, halo (CC) alkyl group, (CC) alkoxy group, which may be the same or different, or

1 6 1 6 1 6

Halo (C—C) alkoxy group power Substituted file with 1 to 5 substituents selected

1 6

A halogen atom, cyan group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy, wherein Q ² may be the same or different.

1 6 1 6 1 6

Group, halo (C—C) alkoxy group, (C—C) alkoxy-oxy group, halo (C—C) al

1 6 2 6 2 6 Keroxy group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C

1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

6 1 6 2 6 Kelthio group, halo (C—C) alkylthio group, (C—C) alkylsulfier

2 6 2 6

Group, halo (C—C) alkylsulfyl group, (C—C) alkylsulfol group,

2 6 1 6

Mouth (C—C) alkyl sulfonyl group, (C—C) alkyl sulfonyl group, halo (C

1 6 2 6 2

C) alkenylsulfol group, mono (C—C) alkylamino group, the same or different

6 1 6

Good di (C—C) alkylamino group, phenolic group, same or different halogen

1 6

1 6 1 6 1

C) alkoxy, halo (C—C) alkoxy, (C—C) alkylthio, halo (C

6 1 6 1 6 1

—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) alkyl

6 1 6 1 6 Sulfiel group, (C—C) alkylsulfo group or halo (C—C) alkylsulfo group

1 6 1 6

-Ru group power Substituted phenol group, phenoxy group or halogen atom, cyan group, nitro group, (C-C) alkyl, which may be the same or different, having 1 to 5 substituents selected

1 6 1 6 1 6

, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyl group

1 6 1 6 1 6 Rufyl group, halo (c -c) alkylsulfier group, (C—C) alkylsulfo-

1 6 1 6

Group or halo (C C) alkylsulfol group with 1 to 5 substituents selected

1 6

A substituted phenol group having 1 to 5 substituents selected from the substituted phenoxy group, wherein R is a hydrogen atom, a (C—C) alkyl group, a halo (C—C) alkyl group, Ciano (C—C

1 6 1 6 1

) Alkyl group, (C—C) alkyl group, halo (C—C) alkenyl group, (C—C)

6 2 10 2 10 2 10 Alkyl group, halo (C—C) alkyl group, (C—C) alkoxycarbole (C

2 10 1 6 1

—C 1) represents an alkyl group or (C—C 1) alkyl carbo yl group, and R ¹ represents a hydrogen atom or (

6 1 6

C—C) alkyl group, R ⁶ represents a hydrogen atom or (C—C) alkyl group, and R 6

1 6 1 3

And R ⁶ together form a 5- to 8-membered ring represented by 1 —X ² —, a carbo group or (CC) alkylene in which X ¹ and X ² may be the same or different. Claim 5 which is a group

1 6

Acetonitrile derivatives listed.

[7] Q ¹ may be the same or different and may be a halogen atom, a halo (C—C) alkyl group or a halo (C

1 6

— C) represents a substituted phenyl group having 1 to 5 substituents selected from alkoxy groups

1 6

, Q ² may be the same or different, halogen atom, halo (C—C) alkyl group, halo (C

1 6 1 C) alkoxy group, phenyl group, halogen atom which may be the same or different, cyan group

6

, Nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy

1 6 1 6 1 6

Or a substituted group having 1 to 5 substituents selected from a halo (C—C) alkoxy group.

1 6

An phenyl group, a phenoxy group, or a halogen atom, cyan group, nitrogen group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, which may be the same or different, or

1 6 1 6 1 6 is a halo (C—C) alkoxy group selected substituted phenoxy having 1 to 5 substituents

1 6

A substituted phenyl group having 1 to 5 substituents selected from the following groups, wherein R is a hydrogen atom, (C—C) alkyl group, (C—C) alkoxycarbole (C—C) An alkyl group or

1 6 1 6 1 6

(C—C) represents an alkyl carbo group, and R ¹ represents a hydrogen atom or a (C—C) alkyl group.

1 6 1 6

R ⁶ represents a hydrogen atom or a (C—C) alkyl group, and R and R ⁶ are

13

X ¹ — X ² — When forming a 5- to 8-membered ring, X ¹ and X ² may be the same or different, and are a carbo group or a (CC) alkylene group. Anyway, force 1

1 6

Acetonitrile derivative.

[8] General formula (I 3)

{In the formula, Ar ¹ represents a phenyl group, a halogen atom which may be the same or different, a nitro group, a cyan group, a (C—C) alkyl group, a halo (C—C) alkyl group, (C—C) Alkoxy group, halo

1 6 1 6 1 6

(C—C) alkoxy group, (C—C) alkenyl group, halo (C—C) alkenyl group, (C

1 6 2 6 2 6 2

—C) alkyl group, (C—C) cycloalkyl group, (C—C) alkoxy group,

6 3 6 2 6

Halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C—C) al

1 6 1 6

-Luoxy group, (C—C) alkyl sulfier group, halo (C—C) alkyl sulfi group

1 6 1 6

Group, (C—C) alkyl sulfonyl group, halo (C—C) alkyl sulfonyl group, (

1 6 1 6

C—C) alkthio group, halo (C—C) alkthio group, (C—C) alkyl group

2 6 2 6 2 6

Rusulfyl group, halo (C—C) alkulsulfyl group, (C—C) alkenyl

2 6 2 6

Sulfol group, halo (C—C) alkaryl sulfonyl group, mono (C—C) alkylamino

2 6 1 6

1 6 1 6

Holamino group, halo (C—C) alkylsulfo-lumino group, (C—C) alkylcal

1 6 1 6

Ball group, halo (C C) alkylcarbol group, (C C) alkyloxycarboxyl

1 6 1 6

6 1 6 1 6 1

) Alkoxy, (C C) alkylthio, halo (C C) alkylthio, (C

6 1 6 1 6 1

C) alkylsulfier group, halo (C—C) alkylsulfier group, (C—C) al

1 6

1 6 1 6

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group, halo

1 6 1 6 1 6

(C—C) alkylthio group, (C—C) alkylsulfier group, halo (C—C) al

1 6 1 6 1 6 Killsulfier group, (C—C) alkylsulfol group or halo (c -c) alkyls

1 6 1 6

A substituted phenyl group having one or more substituents selected from a substituted phenoxy group having one or more substituents selected from a sulfonyl group, an aromatic 6-membered heterocyclic group having 1 or 2 nitrogen atoms, or the same or Different halogen atoms, cyan groups, nitro groups, (C 1 -C 6) alkyl groups, halo (C—C) alkyl groups, (C—C) alkoxy groups, halo (C—C)

6 1 6 1 6 1 6 Lucoxy group, (C — C) alkoxy group, halo (C—C) alkoxy group, (C

2 6 2 6

—C) alkylthio group, halo (C—C) alkylthio group, (C 1 C) alkylsulfi

1 6 1 6 1 6

-Group, halo (C 1 C) alkylsulfinyl group, (C 1 C) alkenylthio group, halo (

1 6 2 6

C—C) alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) a

2 6 2 6 2 6 Lucenylsulfinyl group, (C—C) alkylsulfol group, halo (C—C) alkyl

1 6 1 6 Sulfol group, (C—C) alkanolsulfol group, halo (C—C) alkenyl sulfone

2 6 2 6

-Lu group, mono — C) alkylamino group or di (C—C) which may be the same or different

1 6 1 6

Ar ² represents a fuel group, a halogen atom which may be the same or different, a nitro group, a cyano group, a (C —C) alkyl group, a halo (C—C) alkyl group, a (C—C) alkoxy group, a halo (C one

1 6 1 6 1 6 1

C) alkoxy group, (C 1 C) alkyl group, halo (C 1 C) alkenyl group, (C 1 C)

6 2 6 2 6 2 6 Alkyl group, (C—C) cycloalkyl group, (C—C) alkoxy group, halo (C

3 6 2 6

—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C) alkylthio group

2 6 1 6 1 6

Group, (C 1 C) alkylsulfonyloxy group, halo (C—C) alkylsulfonyl group

1 6 1 6

A xy group, a (C—C) alkylsulfinyl group, a halo (C—C) alkynolesulphinyl group,

1 6 1 6

(C—C) alkylsulfonyl group, halo (C—C) alkylsulfonyl group, (C—C)

2 6 2 6

Nyl group, halo (C—C) alkenylsulfinyl group, (C—C) alkenylsulfonyl

2 6 2 6

2 6 1 6

Or a di (C—C) alkylamino group which may be different, or a (C—C) alkylsulfonyl group.

1 6 1 6

Mino group, halo (C—C) alkylsulfonylamino group, (C—C) alkylcarbonyl group

1 6 1 6

Halo (C 1 C) alkylcarbonyl group, (C 1 C) alkyloxycarbonyl group,

1 6 1 6 Enyl group, halogen atom which may be the same or different, cyan group, nitro group, (C—C) a

1 6 alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (C C) alkyl

1 6 1 6 1 6 Xyl group, (c -c) alkylthio group, halo (c -c) alkylthio group, (c -c) al

1 6 1 6 1 6 Kill sulfinyl group, halo (c -c) alkylsulfinyl group, (C—C) alkyls

1 6 1 6

One or more substituents selected from a sulfonyl group or a halo (C C) alkylsulfonyl group

1 6

Substituted fluorine group, phenoxy group or halogen atom, cyano group, nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C—C), which may be the same or different.

1 6 1 6 1 6

) Alkoxy group, halo (C—C) alkoxy group, (C—C) alkylthio group, halo (C

1 6 1 6 1

C) alkylthio, (C—C) alkylsulfier, halo (C—C) alkyls

6 1 6 1 6

Rufyl group, (C—C) alkyl sulfo group or halo (C—C) alkyl sulfo group

A substituted phenyl group having one or more substituents selected from a substituted phenoxy group having one or more substituents selected from 1 6 1 6 group, an aromatic 6-membered heterocyclic ring having 1 to 2 nitrogen atoms A halogen atom, cyano group, nitro group, (C—C) a which may be the same or different

1 6 alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (C C) alkyl

1 6 1 6 1 6 xy group, (C—C) alkenyloxy group, halo (C—C) alkenyloxy group, (C

2 6 2 6 1

C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfini

6 1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C

1 6 2 6

—C) alkenylthio group, (C—C) alkenylsulfinyl group, halo (C—C) al

2 6 2 6 2 6 Kenylsulfinyl, (C—C) alkylsulfonyl, halo (C—C) alkyls

1 6 1 6

Sulfonyl, (C—C) alkenylsulfonyl, halo (C—C) alkenylsulfonyl

2 6 2 6

1 6 1 6 group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkyl group

2 6 2 6 2 6

, Halo (C—C) alkyl group, (C—C) alkylthio group, halo (CI—C6) alkyl

2 6 1 6

Thio group, (C—C) alkyl carbo group, halo (C—C) alkyl carbo group, (

1 6 1 6

C—C) alkoxycarbonyl group or halo (C—C) alkoxycarbonyl group.

1 6 1 6 ), A sulfur atom or a single bond.

R is a hydrogen atom, (C 1 C) alkyl group, halo (C 1 C) alkyl group, (C 1 C) cyclo

1 6 1 6 3 6 alkyl group, halo (c 1 -C 6) cycloalkyl group, (C 1 C) alkenyl group, halo (C 1

3 6 2 10 2

C) alkyl group, (C—C) alkyl group, halo (C—C) alkyl group, (C 1

10 2 10 2 10 1

C) alkoxycarbonyl (C 1 C) alkyl group, phenyl (C 1 C) alkyl group or

6 1 6 1 6

1 6 1 6 1 6

, (C—C) alkenyloxy, halo (C—C) alkenyloxy, (C—C)

2 6 2 6 1 6 alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfinyl group,

1 6 1 6

Halo (C—C) alkylsulfinyl group, (C—C) alkenylthio group, halo (C—C

1 6 2 6 2 6

) Alkenylthio group, (c—C) alkenylsulfier group, halo (c—C) alkenyl group

2 6 2 6 Nolesnorefininore group, (C—C) anololechnorehoninore group, halo (C—C) anorequinolesnorejo

1 6 1 6

Nyl group, (C—C) alkenylsulfonyl group, halo (C—C) alkenylsulfonyl group

2 6 2 6

, Mono-C) alkylamino group or di (C-C) alkyl which may be the same or different

1 6 1 6 Kiramino group Substituted phenyl having 1 to 5 selected substituents on the ring (C 1 C)

1 6 represents an alkyl group.

R ² represents a hydrogen atom, a (C 1 C) alkyl group, a halo (C 1 C) alkyl group, a cyano (C—C

1 6 1 6 1 6

) Alkyl group, (C 1 C) alkenyl group, halo (C—C) alkenyl group, (C 1 C)

2 10 2 10 2 10 Alkynyl, halo (C 1 C) alkynyl, (C 1 C) alkoxycarbonyl (C

2 10 1 6 1

6 1 6

1 6 1 6 1

—C) alkoxy group, halo (C—C) alkoxy group, (C—C) alkoxyloxy group,

6 1 6 2 6

Halo (C—C) alkenyloxy, (C—C) alkylthio, halo (C—C) al

1 6 1 6

Group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C—C)

2 6 1 6 Killsulfonyl group, /, (C 1 C) alkylsulfol group, (C 1 C) alkenylsulfur group

1 6 2 6

Phonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino group

1 6

Aromatic 6-membered heterocycle (C C) alkyl group or same or different

1 6

1 6 1 6 2 6

Si group, halo (C—C) alkenyloxy group, (C—C) alkylthio group, halo (C—C

2 6 1 6 1 6

) Alkylthio, (C—C) alkylsulfinyl, halo (C—C) alkylsulf

1 6 1 6

Finyl group, (C—C) alkenylthio group, halo (C—C) alkenylthio group, (C

2 6 2 6 2

C) alkenylsulfinyl group, halo (C—C) alkenylsulfinyl group, (C—C)

1 6 2 6

Sulfonyl group, halo (C—C) alkenylsulfonyl group, mono (C—C) alkylamino

2 6 1 6

Group or di (C—C) alkylamino group which may be the same or different

1 6

A substituted aromatic 6-membered heterocyclic (C C) alkyl group having 1 to 2 nitrogen atoms having the above substituent on the ring is shown.

6

1 6

A halo (C—C) alkyl group, a (C—C) cycloalkyl group or a halo (C—C) cycloa

1 6 3 6 3 6 represents an alkyl group, and R ³ and R ⁴ together may form a (C—C) alkylene group.

1 6

it can.

2

Child, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkylcarbo-

1 6 1 6 1 6

Group, halo (C—C) alkylcarbole group, (C—C) alkoxy (C—C) alkyl

1 6 1 6 1 6 group or a (C C) alkoxycarbonyl group. N is 0 or an integer from 1 to 4

1 6

Indicates a number. }

Acetonitrile derivative represented by:

Ar ¹ may be a phenyl group or a halogen atom, nitro group, cyano group, (CC) alkyl group, halo (CC) alkyl group, (CC) alkoxy group, which may be the same or different, or

1 6 1 6 1 6

Halo (C—C) alkoxy group power A substituted phenyl group having one or more selected substituents

1 6

Ar ² is a phenyl group or a halogen atom, a cyan group, which may be the same or different, Nitro group, (CC) alkyl group, halo (CC) alkyl group, (CC) alkoxy group

1 6 1 6 1 6

, Halo (C—C) alkoxy group, (C—C) alkoxy group, halo (C—C) alkke

1 6 2 6 2 6

-Luoxy group, (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C

1 6 1 6 1 6

) Alkyl sulfier group, halo (C—C) alkyl sulfier group, (C—C) alkke

1 6 2 6

-Luthio group, halo (C—C) alkarylthio group, (C—C) alkulsulfyl group

2 6 2 6

, Halo (C—C) alkenylsulfyl group, (C—C) alkylsulfol group, halo (

2 6 1 6

C—C) alkylsulfol group, (C—C) alkylsulfonyl group, halo (C—C)

1 6 2 6 2 6 Alkylsulfol group, mono (C—C) alkylamino group, may be the same or different

1 6

A di (C—C) alkylamino group, a phenol group, a halogen atom which may be the same or different,

1 6

1 6 1 6 1 6 Alkylthio group, (C—C) alkylsulfinyl group, halo (C—C) alkylsulfur group

1 6 1 6

Ynyl, (C—C) alkylsulfonyl or halo (C—C) alkylsulfonyl

1 6 1 6

A substituted phenyl group having one or more substituents selected from the group, a phenoxy group, or a halogen atom, cyan group, nitro group, (C—C) alkyl group, halo, which may be the same or different.

1 6

(C—C) alkyl group, (C—C) alkoxy group, halo (C—C) alkoxy group, (C

1 6 1 6 1 6 1

C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkylsulfini

6 1 6 1 6

Group, halo (C—C) alkylsulfinyl group, (C—C) alkylsulfonyl group or

1 6 1 6

A substituted group having one or more substituents selected from a halo (C—C) alkylsulfonyl group;

6

10 represents a substituted phenyl group having one or more substituents selected from enoxy group, and G represents NR

(Wherein represents a hydrogen atom or (C C alkyl group), a sulfur atom or a single bond.

6

R represents a hydrogen atom or a (C—C) alkyl group, R represents a hydrogen atom, (C—C) a

1 3 1 6 alkyl group, halo (C C) alkyl group, cyano (C C) alkyl group, (C C) alkyl

1 6 1 6 2 10 Kenyl group, halo (C C) alkenyl group, (C C) alkynyl group, halo (C C)

2 10 2 10 2 10 Alkynyl group, (C—C) alkoxycarbonyl (C—C) alkyl group, phenyl (C

1 6 1 6 1

6 1 C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, halo (C C

6 1 6 1 6 1

) Alkoxy group, (c—C) alkenyloxy group, halo (C—C) alkenyloxy group , (C—C) alkylthio group, halo (C—C) alkylthio group, (C—C) alkyls

1 6 1 6 1 6 Rufyl group, halo (c -C) alkylsulfier group, (C—C) alkylthio group

1 6 2 6

, Halo (C—C) alkenylthio group, (C—C) alkenylsulfyl group, halo (C

2 6 2 6 2

—C) alkylsulfyl group, (C—C) alkylsulfol group, halo (C—C)

2 6 2 6 rusulfol group, mono (C C) alkylamino group

1 6

-L (C—C) alkyl group, pyridyl (C—C) alkyl group or the same or different

1 6 1 6

Represents a pyridyl (C—C) alkyl group having 1 to 2 halogen atoms on the ring,

1 6

R ³ and R ⁴ may be the same or different and each represents a hydrogen atom or a (C—C 6) alkyl group,

1 6

9. The acetonitrile derivative according to claim 8, wherein W represents an oxygen atom or a sulfur atom, and n is 0.

[10] Ar ¹ may be the same or different and may be a halogen atom, a halo (C—C) alkyl group or a halo (

1 6

C—C) represents a substituted phenyl group having one or more substituents selected from alkoxy groups

6

Ar ² may be the same or different, halogen atom, halo (C—C) alkyl group, halo (C

6

C) alkoxy group, phenyl group, halogen atom which may be the same or different, cyan group

6

, Nitro group, (C—C) alkyl group, halo (C—C) alkyl group, (C—C) alkoxy

1 6 1 6 1 6

A substituted phenyl having one or more substituents selected from a group or a halo (C—C) alkoxy group

1 6

-Lu group, phenoxy group, or halogen atom, cyan group, -ortho group, (C C) alkyl group, halo (C C) alkyl group, (C C) alkoxy group, which may be the same or different

1 6 1 6 1 6 is a halo (C—C) alkoxy group selected a substituted phenoxy having one or more substituents

1 6

A substituted phenol group having one or more substituents selected from the following groups: G represents NH or a single bond; R represents a (C—C) alkyl group; R ² represents a hydrogen atom; — C) alkyl group

1 3 1 6

, Halo (C—C) alkyl group, (C—C) alkenyl group, halo (C—C) alkenyl

1 6 2 10 2 10

Group, (C—C) alkynyl group, halo (C—C) alkynyl group, (C—C) alkoxy force

2 10 2 10 1 6 Rubonyl (C—C) alkyl group, phenyl (C—C) alkyl group, the same or different

1 6 1 6

Good halogen atom, (C—C) alkyl group, halo (C—C) alkyl group, (C—C)

1-6 1 6 1 6 1-5 substituents selected from an alkoxy group and a halo (CC) alkoxy group on the ring Substituted phenyl (C—C) alkyl group, pyridyl (C—C) alkyl group or the same

1 6 1 6

Alternatively, it may be different and pyridyl (C—C) a having 1 to 2 halogen atoms on the ring.

10. The acetonitrile derivative according to any one of claims 8 or 9, wherein R represents an alkyl group, R ³ and R ⁴ represent a hydrogen atom, W represents an oxygen atom, and n is 0.

[11] A pest control agent comprising the acetonitrile derivative according to any one of claims 1 to 10 as an active ingredient.

[12] Agricultural and horticultural insecticides comprising the acetonitrile derivative according to any one of claims 1 to 10 as an active ingredient.

[13] An animal parasite control agent comprising the acetonitrile derivative according to any one of claims 1 to 10 as an active ingredient.

[14] A method for using an agricultural and horticultural insecticide, which comprises treating an effective amount of the agricultural and horticultural insecticide according to claim 12 with soil, pests or useful plants.

[15] A method for using an animal parasite control agent, which comprises treating an effective amount of the parasite control agent according to claim 13 on the body surface of the animal.

[16] A method for using an animal parasite control agent, comprising administering an effective amount of the parasite control agent according to claim 13 to an animal.