JP2006169117A - Amide compound and use thereof - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new compound having efficacy in controlling plant disease injuries. <P>SOLUTION: The amide compound is represented by formula (1) (wherein, R<SP>1</SP>denotes a hydrogen atom, a halogen atom or the like; R<SP>2</SP>denotes a hydrogen atom, a halogen atom, a 1-6C alkyl group, a 1-6C haloalkyl group, a 2-6C alkenyl group, a 2-6C alkynyl group, a cyano group or a nitro group or R<SP>1</SP>and R<SP>2</SP>together denote a 3-6C alkylene group or the like; R<SP>3</SP>denotes a 1-4C alkyl group, a 1-4C haloalkyl group, a 3-4C alkenyl group, 3-6C alkynyl group or a 2-4C cyanoalkyl group; R<SP>4</SP>denotes a halogen atom, a 1-4C alkyl group, a 1-4C alkoxy group, a 1-4C haloalkoxy group, a 3-4C alkenyloxy group or a 3-4C alkynyloxy group; and R<SP>5</SP>denotes a hydrogen atom, a fluorine atom or a 1-3C alkyl group). <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to an amide compound and use thereof.

Hitherto, drugs for controlling plant diseases have been developed, and many compounds having an activity for controlling plant diseases have been found, but their efficacy may not always be sufficient.
N-benzyl-2-phenoxyacetamide is also known. (For example, compounds described in Patent Document 1 and Patent Document 2)
JP 63-162280 A British Patent Specification GB117485

  An object of the present invention is to provide a compound having an excellent plant disease control effect.

〔式中、
Ｒ¹は水素原子、ハロゲン原子、Ｃ１−Ｃ６アルキル基、Ｃ３−Ｃ６シクロアルキル基、Ｃ１−Ｃ６ハロアルキル基、Ｃ２−Ｃ６アルケニル基、Ｃ２−Ｃ６ハロアルケニル基、Ｃ２−Ｃ６アルキニル基、Ｃ２−Ｃ６ハロアルキニル基、Ｃ１−Ｃ６アルコキシ基、Ｃ３−Ｃ６アルケニルオキシ基、Ｃ３−Ｃ６アルキニルオキシ基、Ｃ１−Ｃ６ハロアルコキシ基、（Ｃ１−Ｃ６アルコキシ）Ｃ１−Ｃ６アルキル基、フェノキシＣ１−Ｃ６アルキル基、ヒドロキシＣ１−Ｃ６アルキル基、Ｃ１−Ｃ６アルキルチオ基、Ｃ１−Ｃ６ハロアルキルチオ基、Ｃ１−Ｃ６アルキルアミノ基、ジ（Ｃ１−Ｃ６アルキル）アミノ基、ホルミル基、（Ｃ１−Ｃ６アルキル）カルボニル基、（Ｃ１−Ｃ６アルコキシ）カルボニル基、（Ｃ１−Ｃ６アルコキシ）イミノＣ１−Ｃ６アルキル基、ベンジルオキシイミノＣ１−Ｃ６アルキル基、フェニル基、フェノキシ基、シアノ基、アミノ基若しくはニトロ基（但し、フェノキシＣ１−Ｃ６アルキル基、フェニル基及びフェノキシ基におけるベンゼン環は、ハロゲン原子、Ｃ１−Ｃ３アルキル基及びＣ１−Ｃ３アルコキシ基から選ばれる基で置換されていてもよい）を表し、
Ｒ²は水素原子、ハロゲン原子、Ｃ１−Ｃ６アルキル基、Ｃ１−Ｃ６ハロアルキル基、Ｃ２−Ｃ６アルケニル基、Ｃ２−Ｃ６アルキニル基、シアノ基若しくはニトロ基を表すか、
あるいはＲ¹とＲ²とが一緒になって、Ｃ３−Ｃ６アルキレン基若しくは−ＣＲ⁵⁰＝ＣＲ⁵¹−ＣＲ⁵²＝ＣＲ⁵³−基（Ｒ⁵⁰、Ｒ⁵¹、Ｒ⁵²及びＲ⁵³は独立して、水素原子、ハロゲン原子、Ｃ１−Ｃ３アルキル基、Ｃ１−Ｃ３アルコキシ基又はＣ１−Ｃ３ハロアルキル基を表す）を表し、
Ｒ³はＣ１−Ｃ４アルキル基、Ｃ１−Ｃ４ハロアルキル基、Ｃ３−Ｃ４アルケニル基、Ｃ３−Ｃ６アルキニル基またはＣ２−Ｃ４シアノアルキル基を表し、
Ｒ⁴はハロゲン原子、Ｃ１−Ｃ４アルキル基、Ｃ１−Ｃ４アルコキシ基、Ｃ１−Ｃ４ハロアルコキシ基、Ｃ３−Ｃ４アルケニルオキシ基又はＣ３−Ｃ４アルキニルオキシ基を表し、
Ｒ⁵は水素原子、フッ素原子又はＣ１−Ｃ３アルキル基を表す。〕
で示されるアミド化合物（以下、本発明化合物と記す。）、本発明化合物を有効成分として含有することを特徴とする植物病害防除剤及び本発明化合物の有効量を植物又は土壌に処理することを特徴とする植物病害防除方法を提供する。 As a result of intensive studies to find a compound having an excellent plant disease control effect, the present inventors have found that the amide compound represented by the following formula (1) has an excellent plant disease control and completed the present invention. .
That is, the present invention provides the formula (1)

[Where,
R ¹ is a hydrogen atom, halogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C1-C6 haloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 Haloalkynyl group, C1-C6 alkoxy group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C1-C6 haloalkoxy group, (C1-C6 alkoxy) C1-C6 alkyl group, phenoxy C1-C6 alkyl group, Hydroxy C1-C6 alkyl group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylamino group, di (C1-C6 alkyl) amino group, formyl group, (C1-C6 alkyl) carbonyl group, C1-C6 alkoxy) carbonyl group, (C1-C6 alkoxy) imino 1-C6 alkyl group, benzyloxyimino C1-C6 alkyl group, phenyl group, phenoxy group, cyano group, amino group or nitro group (however, the benzene ring in the phenoxy C1-C6 alkyl group, phenyl group and phenoxy group is halogenated) And optionally substituted with a group selected from an atom, a C1-C3 alkyl group and a C1-C3 alkoxy group),
R ² represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyano group or a nitro group,
Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or a —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group (R ⁵⁰ , R ⁵¹ , R ⁵² and R ⁵³ are independently Represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group or a C1-C3 haloalkyl group),
R ³ represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group, a C3-C6 alkynyl group or a C2-C4 cyanoalkyl group,
R ⁴ represents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C3-C4 alkenyloxy group or a C3-C4 alkynyloxy group,
R ⁵ represents a hydrogen atom, a fluorine atom or a C1-C3 alkyl group. ]
A plant disease control agent characterized by containing the compound of the present invention as an active ingredient, and treating the plant or soil with an effective amount of the compound of the present invention. Provided is a method for controlling plant diseases.

  Since the compound of the present invention has an excellent plant disease control effect, it is useful as an active ingredient of a plant disease control agent.

In the present invention,
Examples of the halogen atom represented by R ¹ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
C1-C6 alkyl group includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group C1-C4 alkyl group; pentyl group, 2-methylpentyl group A C5-C6 alkyl group such as 3-methylpentyl group, 4-methylpentyl group, hexyl,
Examples of the C3-C6 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
Examples of the C1-C6 haloalkyl group include C1-C4 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, and a trifluoromethyl group.
Examples of the C2-C6 alkenyl group include a vinyl group, 1-methylvinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, and 2-butenyl group. C2-C4 alkenyl groups such as 3-butenyl group; C5-C6 alkenyl groups such as 1-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, and the like.
Examples of the C2-C6 haloalkenyl group include a 2-fluorovinyl group, a 2-chlorovinyl group, a 2-bromovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group, and a 2,2-dibromovinyl group. 1-methyl-2,2-dichlorovinyl group, 1-methyl-2,2-dibrovinyl group,
Examples of the C2-C6 alkynyl group include C2-C4 such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1-butynyl group, 2-butynyl group, and 3-butynyl group. Alkynyl group; C5-C6 alkenyl group such as 3,3-dimethyl-1-butynyl group, 1-pentynyl group, 4-pentynyl group, 1-hexynyl group, 5-hexynyl group, etc.
Examples of the C2-C6 haloalkynyl group include a chloroethynyl group, a bromoethynyl group, an iodoethynyl group, a 2-propynyl group, and a 2-butynyl group.
Examples of the C1-C6 alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, and a C1-C4 alkoxy group of a tert-butoxy group; a pentyloxy group, a hexyloxy group C5-C6 alkoxy groups such as groups,
Examples of the C3-C6 alkenyloxy group include 2-propenyloxy group, 1-methyl-2-propenyloxy group, 2-methyl-2-propenyloxy group, 2-butenyloxy group, 3-butenyloxy group, and 4-pentenyloxy. Group, 5-hexenyloxy group,
Examples of the C3-C6 alkynyloxy group include 2-propynyloxy group, 1-methyl-2-propynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, A 5-hexynyloxy group,
Examples of the C1-C6 haloalkoxy group include a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chloromethyl group, a dichloromethyl group, a trichloromethyl group, a 2,2,2-trifluoroethoxy group, 1,1,2, C1-C4 haloalkoxy groups such as 2-tetrafluoroethoxy group and 2-fluoroethoxy group are mentioned,
(C1-C6 alkoxy) As C1-C6 alkyl group, methoxymethyl group, ethoxymethyl group, propyloxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 2-methoxypropyl group, 2-methoxyisopropyl group Are mentioned,

Examples of the phenoxy C1-C6 alkyl group in which the benzene ring may be substituted with a group selected from a halogen atom, a C1-C3 alkyl group and a C1-C3 alkoxy group include a phenoxymethyl group, a 4-chlorophenoxymethyl group, 4- Methylphenoxymethyl group, 4-methoxyphenoxymethyl group, 1-phenoxyethyl group, 2-phenoxyethyl group, 1-phenoxypropyl group, 3-phenoxypropyl group, 4-phenoxybutyl group,
Examples of the hydroxy C1-C6 alkyl group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, and a 1-hydroxybutyl group.
Examples of the C1-C6 alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, a pentylthio group, and a hexylthio group.
Examples of the C1-C6 haloalkylthio group include a fluoromethylthio group, a difluoromethylthio group, and a trifluoromethylthio group.
Examples of the C1-C6 alkylamino group include a C1-C4 alkylamino group such as a methylamino group, an ethylamino group, a propylamino group, and an isopropylamino group; and a C5-C6 alkylamino group such as a pentylamino group and a hexylamino group. Named,
Examples of the di (C1-C6 alkyl) amino group include C1-C4 dialkylamino groups such as dimethylamino group, diethylamino group and dipropylamino group; C5-C6 dialkylamino groups such as dipentylamino group and dihexylamino group. And
Examples of the (C1-C6 alkyl) carbonyl group include a methylcarbonyl group, an ethylcarbonyl group, a propylcarbonyl group, and an isopropylcarbonyl group.
Examples of the (C1-C6 alkoxy) carbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, and an isopropoxycarbonyl group.
(C1-C6 alkoxy) imino C1-C6 alkyl group includes methoxyiminomethyl group, 1- (methoxyimino) ethyl group, 1- (methoxyimino) propyl group, 1- (methoxyimino) butyl group, ethoxyiminomethyl Group, 1- (ethoxyimino) ethyl group, propoxyiminomethyl group, 1- (isopropoxyimino) ethyl group, butoxyiminomethyl group, pentyloxyiminomethyl group, 1- (hexyloxyimino) ethyl group,
Examples of the benzyloxyimino C1-C6 alkyl group include a benzyloxyiminomethyl group, 1- (benzyloxyimino) ethyl group, 2- (benzyloxyimino) ethyl group, 1- (benzyloxyimino) propyl group, 1- ( Benzyloxyimino) butyl group,
Examples of the phenyl group in which the benzene ring portion may be substituted with a halogen atom, a C1-C3 alkyl group and a C1-C3 alkoxy group include a phenyl group, a 4-chlorophenyl group, a 4-methylphenyl group, 4- A methoxyphenyl group,
Examples of the phenoxy group in which the benzene ring portion may be substituted with a group selected from a halogen atom, a C1-C3 alkyl group and a C1-C3 alkoxy group include a phenoxy group, a 4-chlorophenoxy group, a 4-methylphenoxy group, 4 -A methoxyphenoxy group is mentioned.

Examples of the halogen atom represented by R ² include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of the C1-C6 alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group C1-C4 alkyl group; pentyl group, 2-methylpentyl group C5-C6 alkyl groups such as a group, 3-methylpentyl group, 4-methylpentyl group, and hexyl group,
Examples of the C1-C6 haloalkyl group include a fluoromethyl group, a difluoromethyl group, and a trifluoromethyl group.
Examples of the C2-C6 alkenyl group include a vinyl group, 1-methylvinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, and 2-butenyl group. C2-C4 alkenyl groups such as 3-butenyl group; C5-C6 alkyl groups such as 1-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, and the like.
Examples of the C2-C6 alkynyl group include C2-C4 such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1-butynyl group, 2-butynyl group, and 3-butynyl group. Alkynyl groups; C5-C6 alkynyl groups such as 1-pentynyl group, 4-pentynyl group, 1-hexynyl group, 5-hexynyl group;
Examples of the C3-C6 alkylene group in which R ¹ and R ² are combined include, for example, trimethylene group, tetraethylene group, 2-methylpropane-1,3-diyl group, pentamethylene group, 2-methylbutane-1,4. -C3-C5 alkylene groups such as diyl groups and hexamethylene groups.
Examples of the halogen atom represented by R ⁵⁰ , R ⁵¹ , R ⁵² and R ⁵³ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and examples of the C1-C3 alkyl group include a methyl group, an ethyl group and a propyl group. , An isopropyl group, examples of the C1-C3 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group, and examples of the C1-C3 haloalkyl group include a trifluoromethyl group.
As —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group in which R ¹ and R ² are combined, —CH═CH—CH═CH— group, —CH═CCl—CH═CH— group, -CH = CCl-CCl = CH- _{group, -CH = C (CH 3)} -CH = CH- _{group, -CH = C (CH 3)} -C (CH 3) = CH- group, -CH = C ( OCH ₃ ) —CH═CH— group, —CH═C (CF ₃ ) —CH═CH— group.

Examples of the C1-C4 alkyl group represented by R ³ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
Examples of the C1-C4 haloalkyl group include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, and 2-fluoroethyl. Groups,
Examples of the C3-C4 alkenyl group include a 2-propenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 2-butenyl group, and a 3-butenyl group.
Examples of the C3-C6 alkynyl group include 2-propynyl group, 1-methyl-2-propynyl group, 2-butynyl group, C3-C4 alkynyl group of 3-butynyl group; 1,1-dimethyl-2-propynyl group, 1-methyl-2-butynyl group, 2-pentynyl group, 1-methyl-2-pentynyl group, 4-methyl-2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 2-hexynyl group, 3-hexynyl C5-C6 alkynyl group such as a group,
Examples of the C2-C4 cyanoalkyl group include a cyanomethyl group, a cyanoethyl group, a cyanopropyl group, a 1-methylcyanomethyl group, and a 1,1-dimethylcyanomethyl group.

Examples of the halogen atom represented by R ⁴ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of the C1-C4 alkyl group include a C1-C2 alkyl group of a methyl group or an ethyl group; a C3-C4 alkyl group of a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group. ,
Examples of the C1-C4 alkoxy group include a C1-C2 alkoxy group of a methoxy group and an ethoxy group; a C3-C4 alkoxy group of a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, and a tert-butoxy group. And
Examples of the C1-C4 haloalkoxy group include a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, and a 2-fluoro group. An ethoxy group,
Examples of the C3-C4 alkenyloxy group include a 2-propenyloxy group, a 1-methyl-2-propenyloxy group, a 2-methyl-2-propenyloxy group, a 2-butenyloxy group, and a 3-butenyloxy group.
Examples of the C3-C4 alkynyloxy group include a 2-propynyloxy group, a 1-methyl-2-propynyloxy group, a 2-butynyloxy group, and a 3-butynyloxy group.
The C1-C3 alkyl group represented by R ⁵ is a methyl group, an ethyl group, a propyl group, or an isopropyl group.

As an aspect of this invention, the following compounds are mention | raise | lifted, for example.
An amide compound in which R ⁵ is a hydrogen atom in formula (1);
An amide compound represented by formula (1), wherein R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group;
An amide compound in which R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ⁴ is a chlorine atom, a methyl group or a methoxy group in formula (1);
An amide compound in which R ⁴ is a chlorine atom, a methyl group or a methoxy group and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ⁴ is a C1-C4 alkoxy group in formula (1);
An amide compound in which R ⁴ is a C1-C4 alkoxy group and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ⁴ is a methoxy group in formula (1);
An amide compound in which R ⁴ is a methoxy group and R ⁵ is a hydrogen atom in formula (1);
An amide compound represented by formula (1), wherein R ³ is a C3-C6 alkynyl group;
An amide compound in which R ³ is a C3-C6 alkynyl group and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ³ is a C3-C6 alkynyl group and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group in the formula (1);
An amide compound in which R ³ is a C3-C6 alkynyl group in formula (1), R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ³ is a C3-C6 alkynyl group and R ⁴ is a chlorine atom, a methyl group or a methoxy group in formula (1);
An amide compound in which R ³ is a C3-C6 alkynyl group in formula (1), R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ³ is a C3-C6 alkynyl group and R ⁴ is a C1-C4 alkoxy group in formula (1);
An amide compound in which R ³ is a C3-C6 alkynyl group, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ³ is a C3-C6 alkynyl group and R ⁴ is a methoxy group in formula (1);
An amide compound in which R ³ is a C3-C6 alkynyl group, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ³ is a 2-propynyl group in formula (1);
An amide compound in which R ³ is a 2-propynyl group and R ⁵ is a hydrogen atom in formula (1);

An amide compound in which R ³ is a 2-propynyl group and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group in formula (1);
An amide compound in which R ³ is a 2-propynyl group in formula (1), R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ³ is a 2-propynyl group and R ⁴ is a chlorine atom, a methyl group or a methoxy group in formula (1);
An amide compound in which R ³ is a 2-propynyl group in formula (1), R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ³ is a 2-propynyl group and R ⁴ is a C1-C4 alkoxy group in formula (1);
An amide compound represented by formula (1), wherein R ³ is a 2-propynyl group, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ³ is a 2-propynyl group and R ⁴ is a methoxy group in formula (1);
An amide compound in which R ³ is a 2-propynyl group, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom in formula (1);
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. Amido compounds wherein CR ⁵² = CR ⁵³ -group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ — and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ — and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² = CR ⁵³ -and R ⁴ is a chlorine atom, a methyl group or a methoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;

In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ — and R ⁴ is a C1-C4 alkoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ — and R ⁴ is a methoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² = CR ⁵³ -and R ³ is a C3-C6 alkynyl group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a C3-C6 alkynyl group, and R ⁵ is a hydrogen atom;

In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a C3-C6 alkynyl group, and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. CR ⁵² = CR ⁵³ - a group, R ³ is C3-C6 alkynyl group, R ⁴ is a halogen atom, a C1-C4 alkyl group or C1-C4 alkoxy group, R ² is a hydrogen atom, a halogen atom or A C1-C6 alkyl group, or R ¹ and R ^{2 taken} together are a C3-C6 alkylene group or a —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁵ is a hydrogen atom. An amide compound;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a C3-C6 alkynyl group, and R ⁴ is a chlorine atom, a methyl group or a methoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a C3-C6 alkynyl group, R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a C3-C6 alkynyl group, and R ⁴ is a C1-C4 alkoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a C3-C6 alkynyl group, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a C3-C6 alkynyl group, and R ⁴ is a methoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a C3-C6 alkynyl group, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ — and R ³ is a 2-propynyl group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a 2-propynyl group, and R ⁵ is a hydrogen atom;

In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a 2-propynyl group, and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² = CR ⁵³ -group, R ³ is a 2-propynyl group, R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom; ;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a 2-propynyl group, and R ⁴ is a chlorine atom, a methyl group or a methoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a 2-propynyl group, R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a 2-propynyl group, and R ⁴ is a C1-C4 alkoxy group;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. CR ⁵² = CR ⁵³ -group, R ³ is a 2-propynyl group, R ⁴ is a C1-C4 alkoxy group, R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or An amide compound in which R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁵ is a hydrogen atom;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is 2-propynyl, and R ⁴ is methoxy;
In the formula (1), R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —. An amide compound in which CR ⁵² ═CR ⁵³ —, R ³ is a 2-propynyl group, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ² is a hydrogen atom in formula (1);

An amide compound in which R ² is a hydrogen atom and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ² is a hydrogen atom and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group in formula (1);
An amide compound in which R ² is a hydrogen atom in formula (1), R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ² is a hydrogen atom and R ⁴ is a chlorine atom, a methyl group or a methoxy group in formula (1);
An amide compound in which R ² is a hydrogen atom in formula (1), R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ² is a hydrogen atom and R ⁴ is a C1-C4 alkoxy group in formula (1);
An amide compound in which R ² is a hydrogen atom in formula (1), R ⁴ is a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ² is a hydrogen atom and R ⁴ is a methoxy group in formula (1);
An amide compound in which R ² is a hydrogen atom, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ² is a hydrogen atom and R ³ is a C3-C6 alkynyl group in formula (1);
An amide compound in which R ² is a hydrogen atom, R ³ is a C3-C6 alkynyl group, and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ² is a hydrogen atom, R ³ is a C3-C6 alkynyl group, and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group in formula (1);
In Formula (1), R ² is a hydrogen atom, R ³ is a C3-C6 alkynyl group, R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom. An amide compound;
An amide compound in which R ² is a hydrogen atom, R ³ is a C3-C6 alkynyl group, and R ⁴ is a chlorine atom, a methyl group or a methoxy group in formula (1);
An amide compound in which R ² is a hydrogen atom in formula (1), R ³ is a C3-C6 alkynyl group, R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
An amide compound represented by formula (1), wherein R ² is a hydrogen atom, R ³ is a C3-C6 alkynyl group, and R ⁴ is a C1-C4 alkoxy group;
An amide compound in which R ² is a hydrogen atom in formula (1), R ³ is a C3-C6 alkynyl group, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ² is a hydrogen atom in formula (1), R ³ is a C3-C6 alkynyl group, and R ⁴ is a methoxy group;
An amide compound in which R ² is a hydrogen atom, R ³ is a C3-C6 alkynyl group, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ² is a hydrogen atom and R ³ is a 2-propynyl group in formula (1);
An amide compound in which R ² is a hydrogen atom, R ³ is a 2-propynyl group, and R ⁵ is a hydrogen atom in formula (1);

An amide compound in which R ² is a hydrogen atom, R ³ is a 2-propynyl group, and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group in formula (1);
In Formula (1), R ² is a hydrogen atom, R ³ is a 2-propynyl group, R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom. An amide compound;
An amide compound in which R ² is a hydrogen atom, R ³ is a 2-propynyl group, and R ⁴ is a chlorine atom, a methyl group or a methoxy group in formula (1);
An amide compound in which R ² is a hydrogen atom, R ³ is a 2-propynyl group, R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ² is a hydrogen atom, R ³ is a 2-propynyl group, and R ⁴ is a C1-C4 alkoxy group in formula (1);
An amide compound in which R ² is a hydrogen atom, R ³ is a 2-propynyl group, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ² is a hydrogen atom, R ³ is a 2-propynyl group, and R ⁴ is a methoxy group in formula (1);
An amide compound in which R ² is a hydrogen atom, R ³ is a 2-propynyl group, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom in formula (1);
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1);
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), and R ⁵ is a hydrogen atom;

In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group. An amide compound;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group. An amide compound in which R ⁵ is a hydrogen atom;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), and R ⁴ is a chlorine atom, a methyl group or a methoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is hydrogen An amide compound that is an atom;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group and R ⁴ is a C1-C4 alkoxy group in formula (1);
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom. An amide compound;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), and R ⁴ is a methoxy group;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), and R ³ is a C3-C6 alkynyl group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, and R ⁵ is a hydrogen atom. An amide compound;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, R ⁴ is a halogen atom, C1 An amide compound which is a C4 alkyl group or a C1-C4 alkoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, R ⁴ is a halogen atom, C1 -C4 alkyl or C1-C4 alkoxy groups, amide compounds wherein R ⁵ is hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, R ⁴ is a chlorine atom, methyl An amide compound which is a group or a methoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, R ⁴ is a chlorine atom, methyl An amide compound which is a group or a methoxy group and R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, and R ⁴ is a C1-C4 alkoxy group. An amide compound as a group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, and R ⁴ is a C1-C4 alkoxy group. An amide compound wherein R ⁵ is a hydrogen atom;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, and R ⁴ is a methoxy group. An amide compound;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a C3-C6 alkynyl group, and R ⁴ is a methoxy group An amide compound in which R ⁵ is a hydrogen atom;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), and R ³ is a 2-propynyl group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, and R ⁵ is a hydrogen atom Compound;

In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, R ⁴ is a halogen atom, C1- An amide compound which is a C4 alkyl group or a C1-C4 alkoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, R ⁴ is a halogen atom, C1- An amide compound which is a C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, R ⁴ is a chlorine atom, a methyl group Or an amide compound which is a methoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, R ⁴ is a chlorine atom, a methyl group Or an amide compound which is a methoxy group and R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, and R ⁴ is a C1-C4 alkoxy group. An amide compound;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, and R ⁴ is a C1-C4 alkoxy group. An amide compound in which R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, and R ⁴ is a methoxy group Compound;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ³ is a 2-propynyl group, R ⁴ is a methoxy group, An amide compound in which R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Or an amide compound in which R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Or an amide compound in which R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁵ is a hydrogen atom;

In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁴ is a halogen atom, a C1-C4 alkyl group or C1- An amide compound which is a C4 alkoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁴ is a halogen atom, a C1-C4 alkyl group or C1- An amide compound which is a C4 alkoxy group and R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁴ is a chlorine atom, a methyl group or a methoxy group. Compound;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Or R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ⁴ is a chlorine atom, a methyl group or a methoxy group; An amide compound in which R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, an amide compound in which R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁴ is a C1-C4 alkoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is An amide compound which is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Or an amide compound in which R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁴ is a methoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are combined to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ⁴ is a methoxy group, and R ⁵ is a hydrogen atom. An amide compound;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, an amide compound in which R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ³ is a C3-C6 alkynyl group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁵ is An amide compound which is a hydrogen atom;

In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁴ is An amide compound which is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁴ is A halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² are taken together to form a C3- An amide compound having a C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁴ is An amide compound which is a chlorine atom, a methyl group or a methoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁴ is An amide compound which is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁴ is An amide compound which is a C1-C4 alkoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁴ is An amide compound which is a C1-C4 alkoxy group and R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁴ is An amide compound which is a methoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a C3-C6 alkynyl group, and R ⁴ is An amide compound which is a methoxy group and R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Or an amide compound in which R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, and R ³ is a 2-propynyl group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁵ is hydrogen. An amide compound that is an atom;

In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁴ is a halogen atom. An amide compound which is an atom, a C1-C4 alkyl group or a C1-C4 alkoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁴ is a halogen atom. An amide compound which is an atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁴ is chlorine. An amide compound which is an atom, a methyl group or a methoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁴ is chlorine. An amide compound which is an atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁴ is C1. An amide compound which is a C4 alkoxy group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁴ is C1. -C4 alkoxy group, R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² together, C3-C6 alkylene or -CR ⁵⁰ = CR ⁵¹ An amide compound in which —CR ⁵² ═CR ⁵³ — and R ⁵ is a hydrogen atom;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁴ is methoxy. An amide compound as a group;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, and R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group, R ³ is a 2-propynyl group, and R ⁴ is methoxy. An amide compound wherein R ⁵ is a hydrogen atom;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), and R ² is a hydrogen atom;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), R ² is a hydrogen atom, and R ⁵ is a hydrogen atom;

In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ⁴ is a halogen atom, C1-C4 alkyl An amide compound which is a group or a C1-C4 alkoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ⁴ is a halogen atom, C1-C4 alkyl An amide compound which is a group or a C1-C4 alkoxy group and R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ⁴ is a chlorine atom, a methyl group or a methoxy group An amide compound as a group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ⁴ is a chlorine atom, a methyl group or a methoxy group An amide compound wherein R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ⁴ is a C1-C4 alkoxy group. An amide compound;
In Formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ⁴ is a C1-C4 alkoxy group. An amide compound in which R ⁵ is a hydrogen atom;
An amide compound in which R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group in formula (1), R ² is a hydrogen atom, and R ⁴ is a methoxy group;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ⁴ is a methoxy group, R ⁵ An amide compound in which is a hydrogen atom;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound in which R ⁵ is a hydrogen atom;

In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound wherein R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound wherein R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound wherein R ⁴ is a chlorine atom, a methyl group or a methoxy group;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound wherein R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound wherein R ⁴ is a C1-C4 alkoxy group;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound wherein R ⁴ is a C1-C4 alkoxy group and R ⁵ is a hydrogen atom;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound in which R ⁴ is a methoxy group;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a C3-C6 alkynyl group. An amide compound wherein R ⁴ is a methoxy group and R ⁵ is a hydrogen atom;
In formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, and R ³ is a 2-propynyl group Compound;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁵ is a hydrogen atom;

In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁴ is a halogen atom, a C1-C4 alkyl group or a C1-C4 alkoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁴ is a chlorine atom, a methyl group or a methoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁴ is a chlorine atom, a methyl group or a methoxy group, and R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁴ is a C1-C4 alkoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁴ is a C1-C4 alkoxy group and R ⁵ is a hydrogen atom;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁴ is a methoxy group;
In the formula (1), R ¹ is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group or a C1-C4 alkoxy group, R ² is a hydrogen atom, R ³ is a 2-propynyl group, An amide compound in which R ⁴ is a methoxy group and R ⁵ is a hydrogen atom;

Next, the manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by the following (Production Method 1) to (Production Method 4).

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴及びＲ⁵は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン（以下、ＴＨＦと記す場合がある。）、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル等のエーテル類、ヘキサン、へプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸ブチル、酢酸エチル等のエステル類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド（以下、ＤＭＦと記す場合がある。）等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物があげられる。
反応に用いられる脱水縮合剤としては、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩（以下、ＷＳＣと記す。）、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類があげられる。
式（２）で示される化合物１モルに対して、式（３）で示される化合物が通常１〜３モルの割合、脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常０〜１４０℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物を濾過した後、濾液を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 1)
The compound of the present invention can be produced by reacting the compound represented by the formula (2) with the compound represented by the formula (3) in the presence of a dehydration condensing agent.

[Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include tetrahydrofuran (hereinafter sometimes referred to as THF), ethers such as ethylene glycol dimethyl ether and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane and octane, Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, N, N-dimethylformamide (hereinafter sometimes referred to as DMF) And acid amides, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC) and 1,3-dicyclohexylcarbodiimide.
The compound represented by the formula (3) is usually used in a proportion of 1 to 3 mol and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol per 1 mol of the compound represented by the formula (2).
The reaction temperature of the reaction is usually in the range of 0 to 140 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as filtration of the reaction mixture, extraction of the filtrate with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴及びＲ⁵は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル等のエーテル類、ヘキサン、へプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸ブチル、酢酸エチル等のエステル類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、ジメチルスルホキシド等のスルホキシド類及びこれらの混合物があげられる。
反応に用いられる塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等があげられる。
式（２）で示される化合物１モルに対して、式（４）で示される化合物が通常１〜３モルの割合、塩基が通常１〜１０モルの割合で用いられる。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 2)
The compound of the present invention can be produced by reacting the compound represented by the formula (2) with the compound represented by the formula (4) in the presence of a base.

[Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, And halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and mixtures thereof. .
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. It is done.
The compound represented by the formula (4) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the compound represented by the formula (2).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴及びＲ⁵は前記と同じ意味を表し、Ｌ¹は塩素原子、臭素原子を表す。〕
該反応は、通常溶媒の存在下で行われる。該反応は塩基の存在下に反応を行ってもよい。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル等のエーテル類、ヘキサン、へプタン、オクタン等の脂肪族炭化水素類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸ブチル、酢酸エチル等のエステル類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド、Ｎ−メチルピロリドン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、水及びこれらの混合物があげられる。
反応に用いられる塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩、炭酸水素ナトリウム等のアルカリ金属炭酸水素塩及び水素化ナトリウム等のアルカリ金属水素化物類等があげられる。
式（５）で示される化合物１モルに対して、式（６）で示される化合物が通常１〜２モルの割合であり、塩基が通常１〜２モルの割合で用いられる。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 3)
The compound of the present invention can be produced by reacting the compound represented by the formula (5) with the compound represented by the formula (6).

[Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above, and L ¹ represents a chlorine atom or a bromine atom. ]
The reaction is usually performed in the presence of a solvent. The reaction may be performed in the presence of a base.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. , Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone, etc. Examples thereof include acid amides, sulfoxides such as dimethyl sulfoxide, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydrogen carbonates such as sodium hydrogen carbonate, and alkali metal hydrides such as sodium hydride.
The compound represented by the formula (6) is usually used in a proportion of 1 to 2 mol and the base is usually used in a proportion of 1 to 2 mol with respect to 1 mol of the compound represented by the formula (5).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

〔式中、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴及びＲ⁵は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル等のエーテル類、ヘキサン、へプタン、オクタン等の脂肪族炭化水素類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸ブチル、酢酸エチル等のエステル類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、水及びこれらの混合物があげられる。
反応に用いられる塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩、炭酸水素ナトリウム等のアルカリ金属炭酸水素塩及び水素化ナトリウム等のアルカリ金属水素化物類等があげられる。
式（７）で示される化合物１モルに対して、式（１０）で示される化合物が通常１〜２モルの割合、塩基が通常１〜２モルの割合で用いられる。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production Method 4)
The compound of the present invention includes a compound represented by formula (7) and formula (10)
R ³ -L ² (10)
[Wherein R ³ represents the same meaning as described above, and L ² represents a chlorine atom, a bromine atom, an iodine atom or a methanesulfonyloxy group. ]
It can manufacture by making the compound shown by react.

[Wherein, R ¹ , R ² , R ³ , R ⁴ and R ⁵ represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. , Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, dimethyl Examples thereof include sulfoxides such as sulfoxide, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydrogen carbonates such as sodium hydrogen carbonate, and alkali metal hydrides such as sodium hydride.
The compound represented by the formula (10) is usually used in a proportion of 1 to 2 mol and the base is usually used in a proportion of 1 to 2 mol with respect to 1 mol of the compound represented by the formula (7).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

〔式中、Ｒ³、Ｒ⁴及びＲ⁵は前記と同じ意味を表し、Ｌ⁴は塩素原子、臭素原子を表す。〕 Some of the intermediates used in the production of the compound of the present invention are commercially available or disclosed in known literatures. The intermediate of the present invention can be produced, for example, by the following method.
(Intermediate production method 1)
The compound represented by the formula (3) and the compound represented by the formula (4) can be produced by the method represented by the following formula.

[Wherein R ³ , R ⁴ and R ⁵ represent the same meaning as described above, and L ⁴ represents a chlorine atom or a bromine atom. ]

(Process 1)
In accordance with the method described in J. Org. It can be produced by reacting in the presence of sodium bromide.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used for the reaction include alcohols such as methanol and ethanol.
Sodium thiocyanate is usually used in a proportion of 1 to 5 mol, bromine is usually used in a proportion of 1 to 2 mol, and sodium bromide is usually used in a proportion of 1 to 2 mol relative to 1 mol of the compound represented by the formula (M1). .
The reaction temperature of the reaction is usually in the range of -20 to 30 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (M2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound represented by the formula (M2) can be further purified by chromatography, recrystallization and the like.

(Process 2)
The compound represented by the formula (M3) can be produced by reacting the compound represented by the formula (M2) with lithium aluminum hydride.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and mixtures thereof.
Lithium aluminum hydride is usually used at a ratio of 0.5 to 2 mol with respect to 1 mol of the compound represented by the formula (M2).
The reaction temperature is usually in the range of −20 to 50 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (M3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound represented by the formula (M3) can be further purified by chromatography, recrystallization and the like.

(Process 3)
The compound represented by the formula (M4) can be produced by reacting the compound represented by the formula (M3) and the compound represented by the formula (M3-1) in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. , Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, dimethyl Examples thereof include sulfoxides such as sulfoxide, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
The compound represented by the formula (M3-1) is usually used at a ratio of 1 to 2 mol and the base is usually used at a ratio of 1 to 2 mol with respect to 1 mol of the compound represented by the formula (M3).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (M4) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound represented by the formula (M4) can be further purified by chromatography, recrystallization and the like.

(Process 4)
The compound represented by the formula (M5) includes the compound represented by the formula (M4) and the formula (M4-1).
R ³ -L ² (M4-1)
[Wherein R ³ and L ² represent the same meaning as described above. ]
It can manufacture by making it react with the compound shown by presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. , Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, dimethyl Examples thereof include sulfoxides such as sulfoxide, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
The compound represented by the formula (M4-1) is usually used in a proportion of 1 to 2 mol and the base is usually used in a proportion of 1 to 2 mol with respect to 1 mol of the compound represented by the formula (M4).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (M5) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound represented by the formula (M5) can be further purified by chromatography, recrystallization and the like.

(Process 5)
The compound represented by the formula (3) can be produced by reacting the compound represented by the formula (M5) with water in the presence of a base.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, alcohols such as methanol and ethanol, and mixtures thereof.
Examples of the base used in the reaction include alkali metal hydroxides such as lithium hydroxide, potassium hydroxide and sodium hydroxide.
Water is usually used in a proportion of 1 mol to a large excess and a base is usually used in a proportion of 1 to 2 mol with respect to 1 mol of the compound represented by formula (M5).
The reaction temperature of the reaction is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound represented by the formula (3) can be further purified by chromatography, recrystallization and the like.

(Step 6)
The compound represented by the formula (4) can be produced by reacting the compound represented by the formula (3) with thionyl chloride.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, and mixtures thereof.
Thionyl chloride is usually used in a ratio of 1 mol to 10 mol with respect to 1 mol of the compound represented by the formula (3).
The reaction temperature is usually in the range of 20 to 150 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (4) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer. The isolated compound represented by the formula (4) can be further purified by chromatography, recrystallization and the like.

〔式中、Ｌ¹、Ｒ¹、Ｒ²、Ｒ⁴及びＲ⁵は前記と同じ意味を表す。〕 (Intermediate production method 2)

[Wherein, L ¹ , R ¹ , R ² , R ⁴ and R ⁵ represent the same meaning as described above. ]

(Process 1)
The compound represented by the formula (5) can be produced by further reacting the compound represented by the formula (M8) with the reaction product of the compound represented by the formula (M9) and the carbodiimide compound.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, and the like. These mixtures can be mentioned.
Examples of the carbodiimide compound used for the reaction include WSC.
The compound represented by the formula (M8) is usually used in a proportion of 0.5 to 1 mol and the carbodiimide compound is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound represented by the formula (M9).
The reaction temperature of the reaction is usually in the range of -20 to 80 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound represented by the formula (5) can be isolated by performing post-treatment operations such as filtering the reaction mixture, extracting the filtrate with an organic solvent, and drying and concentrating the organic layer. it can. The isolated compound represented by the formula (5) can be further purified by chromatography, recrystallization and the like.

(Process 2)
The compound represented by the formula (7) can be produced by reacting the compound represented by the formula (5) with the compound represented by the formula (M10).
The reaction is usually performed in the presence of a solvent. The reaction may be performed in the presence of a base.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone. , Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone, etc. Examples thereof include acid amides, sulfoxides such as dimethyl sulfoxide, water, and mixtures thereof.
Examples of the base that may be used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, and alkali metal hydrides such as sodium hydride.
The compound represented by the formula (M10) is usually used in a proportion of 1 to 5 mol and the base is usually used in a proportion of 1 to 2 mol with respect to 1 mol of the compound represented by the formula (5).
The reaction temperature of the reaction is usually in the range of 30 to 150 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (7) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound represented by the formula (7) can be further purified by chromatography, recrystallization and the like.

［式中、Ｒ¹及びＲ²は前記と同じ意味を表す。］
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えば１，４−ジオキサン、テトラヒドロフラン、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類及びこれらの混合物が挙げられる。
反応に用いられる還元剤としては、例えば水素化アルミニウムリチウム、ジイソブチルアルミニウムヒドリド等の金属水素化物が挙げられる。
式（Ｍ２０）で示される化合物１モルに対して、還元剤は通常０．５〜５モルの割合で用いられるが、還元剤の種類により適宜変更することができる。
反応終了後は、反応混合物を水に注加して有機溶媒抽出し、有機層を必要に応じて塩基性水（水酸化ナトリウム水溶液等）で洗浄してから、乾燥、濃縮する等の後処理操作を行うことにより、式（２）で示される化合物を単離することができる。単離された式（２）で示される化合物は、蒸留、クロマトグラフィー等の操作によりさらに精製することもできる。 (Intermediate production method 3)
The compound represented by the formula (2) can be produced, for example, by reacting the compound represented by the formula (M20) with a reducing agent.

[Wherein, R ¹ and R ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Group hydrocarbons and mixtures thereof.
Examples of the reducing agent used in the reaction include metal hydrides such as lithium aluminum hydride and diisobutylaluminum hydride.
The reducing agent is usually used in a proportion of 0.5 to 5 mol with respect to 1 mol of the compound represented by the formula (M20), but can be appropriately changed depending on the kind of the reducing agent.
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent, and the organic layer is washed with basic water (sodium hydroxide aqueous solution, etc.) as necessary, and then dried and concentrated. By performing the operation, the compound represented by the formula (2) can be isolated. The isolated compound represented by the formula (2) can be further purified by operations such as distillation and chromatography.

［式中、Ｒ¹、Ｒ²及びＬ¹は前記と同じ意味を表す。］ (Intermediate production method 4)
The compound represented by the formula (2) can be produced, for example, by the method represented by the following formula.

[Wherein R ¹ , R ² and L ¹ represent the same meaning as described above. ]

(Process 1)
The compound represented by the formula (M22) can be produced by reacting the compound represented by the formula (M21) with potassium phthalimide.
The reaction is usually performed in the presence of a solvent.
Solvents used for the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and butyronitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, Water and mixtures thereof are mentioned.
Potassium phthalimide is usually used at a ratio of 1 to 3 moles with respect to 1 mole of the compound represented by the formula (M21).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (M22) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated compound represented by the formula (M22) can be further purified by operations such as chromatography, recrystallization and the like.

(Process 2)
The compound represented by the formula (2) can be produced by reacting the compound represented by the formula (M22) with hydrazine.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol, ethanol and propanol, water, and mixtures thereof.
Hydrazine used in the reaction may be a hydrate. Hydrazine is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the compound represented by the formula (M22).
The reaction temperature is usually in the range of 0 to 150 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (2) is simply obtained by performing post-treatment operations such as filtering the reaction mixture, adding water to the filtrate, extracting with an organic solvent, and drying and concentrating the organic layer. Can be separated. The isolated compound represented by the formula (2) can be further purified by operations such as distillation and chromatography.

［式中、Ｒ¹及びＲ²は前記と同じ意味を表す。］
該反応は、溶媒の存在下に行ってもよく、該溶媒としては、例えば１，４−ジオキサン、テトラヒドロフラン、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル等のエーテル類、ヘキサン、ヘプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類及びこれらの混合物が挙げられる。
式（Ｍ２３）で示される化合物１モルに対して、ホルムアミドは通常１〜１５モルの割合、蟻酸は通常０．１〜２モルの割合で用いられる。
反応終了後は、反応混合物を水に注加して有機溶媒抽出し、有機層を必要に応じて塩基性水（水酸化ナトリウム水溶液等）で洗浄してから、乾燥、濃縮する等の後処理操作を行うことにより、式（２）で示される化合物を単離することができる。単離された式（２）で示される化合物は、蒸留、クロマトグラフィー等の操作によりさらに精製することもできる。 (Intermediate production method 5)
The compound represented by the formula (2) can be produced, for example, by reacting the compound represented by the formula (M23) with formamide in the presence of formic acid.

[Wherein, R ¹ and R ² represent the same meaning as described above. ]
The reaction may be performed in the presence of a solvent. Examples of the solvent include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, and fats such as hexane, heptane, and octane. Aromatic hydrocarbons such as aromatic hydrocarbons, toluene and xylene, and mixtures thereof.
Formamide is usually used in a proportion of 1 to 15 mol and formic acid is usually used in a proportion of 0.1 to 2 mol with respect to 1 mol of the compound represented by the formula (M23).
After completion of the reaction, the reaction mixture is poured into water and extracted with an organic solvent, and the organic layer is washed with basic water (sodium hydroxide aqueous solution, etc.) as necessary, and then dried and concentrated. By performing the operation, the compound represented by the formula (2) can be isolated. The isolated compound represented by the formula (2) can be further purified by operations such as distillation and chromatography.

［式中、Ｒ¹及びＲ²は前記と同じ意味を表す。］ (Intermediate production method 6)
The compound represented by the formula (2) can be produced, for example, by the method represented by the following formula.

[Wherein, R ¹ and R ² represent the same meaning as described above. ]

(Process 1)
The compound represented by the formula (M25) can be produced by reacting the compound represented by the formula (M24) with hydroxylamine.
The reaction is usually performed in the presence of a solvent.
Solvents used for the reaction include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene. Hydrocarbons, halogenated hydrocarbons such as chlorobenzene, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and butyronitrile, acid amides such as N, N-dimethylformamide, sulfoxides such as dimethyl sulfoxide, Examples thereof include alcohols such as methanol, ethanol, propanol and isopropanol, water, and mixtures thereof.
Hydroxylamine is usually used at a ratio of 1 to 5 moles with respect to 1 mole of the compound represented by the formula (M24).
The reaction temperature is usually in the range of 0 to 150 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (M25) can be isolated by performing post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated compound represented by the formula (M25) can be further purified by operations such as chromatography, recrystallization and the like.

(Process 2)
The compound represented by the formula (2) can be produced by reacting the compound represented by the formula (M25) with hydrogen in the presence of a hydrogenation catalyst.
The reaction is carried out under a hydrogen atmosphere, usually in the presence of a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol, ethanol and propanol, esters such as ethyl acetate and butyl acetate, ethers such as tetrahydrofuran and 1,4-dioxane, and mixtures thereof.
Examples of the hydrogenation catalyst used in the reaction include transition metal compounds such as palladium carbon, palladium hydroxide, Raney nickel, and platinum oxide.
Hydrogen is usually used in a proportion of 2 mol and the hydrogenation catalyst is usually used in a proportion of 0.001 to 0.5 mol with respect to 1 mol of the compound represented by the formula (M25).
The reaction is usually performed under a hydrogen atmosphere at 1 to 100 atm. An acid (hydrochloric acid etc.) can also be added as needed.
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound represented by the formula (2) is isolated by performing post-treatment operations such as filtering the reaction mixture, extracting the filtrate with an organic solvent, and drying and concentrating the obtained organic layer. be able to. The isolated compound represented by the formula (2) can be further purified by operations such as chromatography and recrystallization.

上記式（Ａ）において、Ｒ¹、Ｒ²、Ｒ³及びＲ⁴の各置換基は、（表１）〜（表１２）に記載された組み合わせである。 Next, specific examples of the compound of the present invention are shown below.
-Compound represented by formula (A)

In said formula (A), each substituent of R < ¹ >, R < ² >, R < ³ > and R < ⁴ > is the combination described in (Table 1)-(Table 12).

上記式（Ｂ）におけるＲ¹、Ｒ²、Ｒ³及びＲ⁴の各置換基は、上記の（表１）〜（表１２）に記載された組合わせである。 -Compound represented by formula (B)

Each substituent of R < ¹ >, R < ² >, R < ³ > and R < ⁴ > in the above formula (B) is a combination described in the above (Table 1) to (Table 12).

Examples of plant diseases that the compounds of the present invention have a controlling effect include plant diseases caused by algae, and specific examples include the following diseases.
Sugar beet, downy mildew (Peronospora brassicae), spinach downy mildew (Peronospora spinaciae), tobacco downy mildew (Peronospora tabacina), downy mildew downy mildew (Pseudoperonospora cubensis), grape downy mildew ( Plasmopara viticola), apple, strawberry, garlic (Phytophthora cactorum), tomato, cucumber gray plague (Photosphere capsici), pineapple plague (Phytophthora cinnamomi), potato, tomato plague (Phytophthora infestans), tobacco, broad bean , Leek plague (Phytophthora nicotianae var. Nicotianae), spinach blight (Pythium sp.), Cucumber seedling blight (Pythium aphanidermatum), wheat brown snow rot (Pythium sp.), Tobacco seedling blight ( Pythium debaryanum), soybean Pythium rot (Pythium aphanidermatum, P. debaryanum, P. irregulare, P. myriotylum, P. ultimum).

  The plant disease control agent of the present invention may be the compound of the present invention itself, but usually mixed with a solid carrier, a liquid carrier, a surfactant or other formulation adjuvants to give an emulsion, a wettable powder, a granular wettable powder. It is formulated into flowables, powders, granules and the like. These preparations usually contain 0.1 to 90% by weight of the compound of the present invention.

  Examples of solid carriers used in the formulation include kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob flour, walnut shell powder, etc. Natural organic materials, synthetic organic materials such as urea, salts such as calcium carbonate and ammonium sulfate, fine powders or granular materials made of synthetic inorganic materials such as synthetic hydrous hydroxide, etc., and liquid carriers include, for example, xylene, alkylbenzene, methyl Aromatic hydrocarbons such as naphthalene, alcohols such as 2-propanol, ethylene glycol, propylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, and petroleum aliphatic hydrocarbons , Esters, dimethyls Sulfoxide, acetonitrile, water and the like.

  Examples of surfactants include anionic interfaces such as alkyl sulfate esters, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates, and the like. Nonionic surfactants such as activators and polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters and the like.

  Examples of other adjuvants for preparation include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethylcellulose) and xanthan gum, aluminum magnesium silicate, alumina sol And stabilizers such as inorganic substances such as preservatives, colorants, PAP (isopropyl acid phosphate) and BHT.

  The plant disease control agent of the present invention is used to protect the plant from plant diseases, for example, by treating the plant body, and also protects plants growing in the soil from plant diseases by treating the soil. Used for.

When the plant disease control agent of the present invention is used by treating the plant body with foliage treatment or by treating it with soil, the treatment amount depends on the type of crop, the type of disease to be controlled, and the control type. Although it can be changed depending on the degree of occurrence of the target disease, preparation form, treatment time, weather conditions, etc., it is usually 1 to 5000 g, preferably 5 to 1000 g as the compound of the present invention per 10,000 m ² .

  Emulsions, wettable powders, flowables and the like are usually treated by diluting with water and spraying. In this case, the concentration of the compound of the present invention is usually 0.0001 to 3% by weight, preferably 0.0005 to 1% by weight. Powders, granules, etc. are usually processed without dilution.

  Moreover, the plant disease control agent of this invention can also be used by processing methods, such as seed disinfection. As the method, for example, a method of immersing a plant seed in the plant disease control agent of the present invention prepared so that the concentration of the compound of the present invention is 1-1000 ppm, the concentration of the compound of the present invention is 1-1000 ppm in the plant seed. And the method of spraying or smearing the plant disease control agent of the present invention and the method of dressing the plant disease control agent of the present invention on plant seeds.

  In the plant disease control method of the present invention, the effective amount of the plant disease control agent of the present invention is usually treated to the plant where the occurrence of the disease is predicted or the soil where the plant grows, and / or the occurrence of the disease is confirmed. It is carried out by treating the plant or the soil where the plant grows.

The plant disease control agent of the present invention is usually used as a plant disease control agent for agricultural and horticultural use, that is, a plant disease control agent for controlling plant diseases such as upland, paddy fields, orchards, tea gardens, pastures, and lawns.
The plant disease control agent of the present invention can be used together with other plant disease control agents, insecticides, acaricides, nematicides, herbicides, plant growth regulators and / or fertilizers.

  Examples of active ingredients of such plant disease control agents include, Ziram, dineb, propineb, etc.), inorganic or organic copper derivatives (basic copper sulfate, basic copper chloride, copper hydroxide, oxine copper, etc.), acylalanine derivatives (metalaxyl, furaxyl, off race, cyprofuran, benalaxyl, oxadixyl) ), Strobilurin compounds (cresoxime methyl, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, etc.), anilinopyrimidine derivatives (cyprodinil, pyrimethanil, mepa) Pyrim, etc.), phenylpyrrole derivatives (phenpiclonyl, fludioxonil, etc.), imide derivatives (procymidone, iprodione, vinclozoline, etc.), benzimidazole derivatives (carbendazim, benomyl, thiabendazole, thiophanatemethyl, etc.), amine derivatives (fenpropimorph, tridemorph, phen) Propidine, spiroxamine, etc.), azole derivatives (propiconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraco Nazole, Microbutanyl, Fenbuconazole, Hexaconazole, Fluquinconazole, Tritico Sol, viteltanol, imazalyl, flutriahol, etc.), simoxanil, dimethomorph, famoxadone, fenamidone, iprovaricarb, benchavaricarb, cyazofamide, zoxamide, ethaboxam, boscalid, fenhexamide, quinoxyphene, dietofencarb, fluopicolide, and fluopicolide Lar S-methyl.

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）： ２．１６（３Ｈ，ｓ）、２．３３（３Ｈ，ｓ）、２．５１（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、３．５９（２Ｈ，ｓ）、４．３９（２Ｈ，ｄ，Ｊ＝６．０Ｈｚ）、４．７０（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８５（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）、７．０１−７．１４（７Ｈ，ｍ） Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, a test example, etc., this invention is not limited only to these examples.
First, the manufacture example of this invention compound is shown.
Production Example 1
To 20 ml of acetonitrile, 0.30 g of 4-mercapto-2-methylphenol, 0.54 g of N- (4-methylbenzyl) -2-bromoacetamide and 0.70 g of cesium carbonate were added, and the mixture was stirred for 1 hour. To the mixture, 0.26 g of 2-bromopropyne and 0.70 g of cesium carbonate were added, and this was stirred at room temperature for 30 minutes and under reflux conditions for 1 hour. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and N- (4-methylbenzyl) -2- (3-methyl-4- (2-propynyloxy) phenylthio) acetamide (hereinafter referred to as the present compound 1). .) 0.25 g was obtained.
Compound 1 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.16 (3H, s), 2.33 (3H, s), 2.51 (1H, t, J = 2.4 Hz); 59 (2H, s), 4.39 (2H, d, J = 6.0 Hz), 4.70 (2H, d, J = 2.4 Hz), 6.85 (1H, d, J = 8.4 Hz) ), 7.01-7.14 (7H, m)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．５４（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、２．６３（２Ｈ，ｓ）、３．７７（３Ｈ，ｓ）、４．３９（２Ｈ，ｄ，Ｊ＝９．９Ｈｚ）、４．７５（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８０−６．８４（２Ｈ，ｍ）、６．９１−６．９５（１Ｈ，ｍ）、７．０２（２Ｈ，ｄ，Ｊ＝８．３Ｈｚ）、７．０８（１Ｈ，ｂｒ）、７．２２（２Ｈ，ｄ，Ｊ＝８．３Ｈｚ） Production Example 2
To 4 ml of DMF were added 2 ml of pyridine, 0.28 g of 4-chlorobenzylamine, 0.50 g of 2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetic acid and 0.49 g of WSC, and the mixture was heated at 80 ° C. for 30 minutes. Stir at room temperature for 6 hours. Dilute hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and N- (4-chlorobenzyl) -2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetamide (hereinafter referred to as the present compound 2). .) 0.34 g was obtained.
Compound 2 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.54 (1H, t, J = 2.4 Hz), 2.63 (2H, s), 3.77 (3H, s), 4. 39 (2H, d, J = 9.9 Hz), 4.75 (2H, d, J = 2.4 Hz), 6.80-6.84 (2H, m), 6.91-6.95 (1H M), 7.02 (2H, d, J = 8.3 Hz), 7.08 (1H, br), 7.22 (2H, d, J = 8.3 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．５２（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、３．６５（２Ｈ，ｓ）、３．７６（３Ｈ，ｓ）、４．４４（２Ｈ，ｄ，Ｊ＝６．０Ｈｚ）、４．７５（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８２−６．８７（２Ｈ，ｍ）、６．９３−６．９６（１Ｈ，ｍ）、７．０３（１Ｈ，ｂｒ）、７．１０−７．１３（２Ｈ，ｍ）、７．１８−７．３０（３Ｈ，ｍ） Production Example 3
To 2 ml of DMF were added 0.11 g of benzylamine, 0.20 g of 2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetic acid and 0.20 g of WSC, and the mixture was stirred at 30 ° C. for 5 hours and allowed to stand at room temperature overnight. I put it. 10 ml of water was added to the reaction mixture, and the mixture was extracted with 8 ml of ethyl acetate. The organic layer was washed with 11 ml of brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.07 g of N-benzyl-2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetamide (hereinafter referred to as the present compound 3). Got.
Compound 3 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.52 (1H, t, J = 2.4 Hz), 3.65 (2H, s), 3.76 (3H, s), 4. 44 (2H, d, J = 6.0 Hz), 4.75 (2H, d, J = 2.4 Hz), 6.82-6.87 (2H, m), 6.93-6.96 (1H M), 7.03 (1H, br), 7.10-7.13 (2H, m), 7.18-7.30 (3H, m)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．５４（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、３．６５（２Ｈ，ｓ）、３．７８（３Ｈ，ｓ）、４．３８（２Ｈ，ｄ，Ｊ＝６．０Ｈｚ）、４．７６（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８１−６．８４（２Ｈ，ｍ）、６．９６（２Ｈ，ｄ，Ｊ＝８．４Ｈｚ）、７．０４（１Ｈ，ｂｒ）、７．２６（１H，ｓ）、７．３８（２Ｈ，ｄ，Ｊ＝８．４Ｈｚ） Production Example 4
N- (4-Bromobenzyl) -2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetic acid was used in the same manner as in Production Example 3, except that 4-bromobenzylamine was used instead of benzylamine. 0.10 g of an amide (hereinafter referred to as the present compound 4) was obtained.
Compound 4 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.54 (1H, t, J = 2.4 Hz), 3.65 (2H, s), 3.78 (3H, s), 4. 38 (2H, d, J = 6.0 Hz), 4.76 (2H, d, J = 2.4 Hz), 6.81-6.84 (2H, m), 6.96 (2H, d, J = 8.4 Hz), 7.04 (1 H, br), 7.26 (1 H, s), 7.38 (2 H, d, J = 8.4 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．３２（３Ｈ，ｓ）、２．５１（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、３．６３（２Ｈ，ｓ）、３．７６（３Ｈ，ｓ）、４．３９（２Ｈ，ｄ，Ｊ＝４．０Ｈｚ）、４．７４（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８２−６．８７（２Ｈ，ｍ）、６．９３−６．９７（２Ｈ，ｍ）、７．０１（２Ｈ，ｄ，Ｊ＝８．４Ｈｚ）、７．０８（２Ｈ，ｄ，Ｊ＝８．４Ｈｚ） Production Example 5
N- (4-Methylbenzyl) -2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetic acid was used in the same manner as in Production Example 3, using 4-methylbenzylamine instead of benzylamine. 0.12 g of amide (hereinafter referred to as the present compound 5) was obtained.
Compound 5 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.32 (3H, s), 2.51 (1H, t, J = 2.4 Hz), 3.63 (2H, s), 3. 76 (3H, s), 4.39 (2H, d, J = 4.0 Hz), 4.74 (2H, d, J = 2.4 Hz), 6.82-6.87 (2H, m), 6.93-6.97 (2H, m), 7.01 (2H, d, J = 8.4 Hz), 7.08 (2H, d, J = 8.4 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．５２（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、３．６５（２Ｈ，ｓ）、３．８０（３Ｈ，ｓ）、４．３９（２Ｈ，ｄ，Ｊ＝６．０Ｈｚ）、４．７５（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８１−６．８４（２Ｈ，ｍ）、６．９０−６．９７（２Ｈ，ｍ）、７．１０（１H，ｂｒ）、７．２３（１Ｈ，ｄ，Ｊ＝２．０Ｈｚ）、７．３２（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ） Production Example 6
Instead of benzylamine, N- (3,4-dichlorobenzyl) -2- (3-methoxy-4- (2-propynyloxy) was used in the same manner as in Production Example 3, using 3,4-dichlorobenzylamine. 0.19 g of phenylthio) acetamide (hereinafter referred to as the present compound 6) was obtained.
Compound 6 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.52 (1H, t, J = 2.4 Hz), 3.65 (2H, s), 3.80 (3H, s), 4. 39 (2H, d, J = 6.0 Hz), 4.75 (2H, d, J = 2.4 Hz), 6.81-6.84 (2H, m), 6.90-6.97 (2H M), 7.10 (1H, br), 7.23 (1H, d, J = 2.0 Hz), 7.32 (1H, d, J = 8.4 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．０２−２．１０（２H，ｍ）、２．５１（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、２．８２−２．８９（４H，ｍ）、３．６３（２Ｈ，ｓ）、３．７６（３Ｈ，ｓ）、４．３９（２Ｈ，ｄ，Ｊ＝５．６Ｈｚ）、４．７４（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８２−７．００（６Ｈ，ｍ）、７．１２（１H，ｄ，J=７．６Hz） Production Example 7
To 2 ml of DMF is added 0.19 g of 5-indanylmethylamine hydrochloride, 0.20 g of 2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetic acid, 0.20 g of WSC and 0.3 ml of triethylamine, and the mixture is mixed with 30 ml. The mixture was stirred at 0 ° C. for 5 hours and allowed to stand overnight at room temperature. 10 ml of water was added to the reaction mixture, and the mixture was extracted with 8 ml of ethyl acetate. The organic layer was washed with 11 ml of brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and N- (5-indanylmethyl) -2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetamide (hereinafter referred to as the present compound 7). 0.09 g was obtained.
Compound 7 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.02-2.10 (2H, m), 2.51 (1H, t, J = 2.4 Hz), 2.82-2.89 (4H, m), 3.63 (2H, s), 3.76 (3H, s), 4.39 (2H, d, J = 5.6 Hz), 4.74 (2H, d, J = 2) .4 Hz), 6.82-7.00 (6 H, m), 7.12 (1 H, d, J = 7.6 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：１．７６−１．７９（４H，ｍ）、２．５１（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、２．６８−２．７３（４H，ｍ）、３．６３（２Ｈ，ｓ）、３．７６（３Ｈ，ｓ）、４．３６（２Ｈ，ｄ，Ｊ＝５．６Ｈｚ）、４．７４（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８２−６．８８（４Ｈ，ｍ）、６．９４−６．９９（３H，ｍ） Production Example 8
In place of benzylamine, N- (5,6,7,8-tetrahydro-2-methylamine was used in the same manner as in Production Example 3, using (5,6,7,8-tetrahydro-2-naphthyl) methylamine. 0.08 g of naphthyl) methyl-2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetamide (hereinafter referred to as the present compound 8) was obtained.
Compound 8 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.76-1.79 (4H, m), 2.51 (1H, t, J = 2.4 Hz), 2.68-2.73 (4H, m), 3.63 (2H, s), 3.76 (3H, s), 4.36 (2H, d, J = 5.6 Hz), 4.74 (2H, d, J = 2) .4 Hz), 6.82-6.88 (4H, m), 6.94-6.99 (3H, m)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．４９（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、３．６７（２Ｈ，ｓ）、３．６８（３Ｈ，ｓ）、４．６０（２Ｈ，ｄ，Ｊ＝６．０Ｈｚ）、４．６９（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８１−６．８９（３Ｈ，ｍ）、７．１３（１H，ｂｒ）、７．２２（１H，ｄｄ，Ｊ＝８．０Ｈｚ，２．０Ｈｚ）、７．４４−７．５０（２H，ｍ）、７．５７（１Ｈ，ｓ）、７．７０−７．８２（３Ｈ，ｍ） Production Example 9
N- (2-naphthylmethyl) -2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetic acid was used in the same manner as in Production Example 3, using 2-naphthylmethylamine instead of benzylamine. 0.07 g of amide (hereinafter referred to as the present compound 9) was obtained.
Compound 9 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.49 (1H, t, J = 2.4 Hz), 3.67 (2H, s), 3.68 (3H, s), 4. 60 (2H, d, J = 6.0 Hz), 4.69 (2H, d, J = 2.4 Hz), 6.81-6.89 (3H, m), 7.13 (1H, br), 7.22 (1H, dd, J = 8.0 Hz, 2.0 Hz), 7.44-7.50 (2H, m), 7.57 (1H, s), 7.70-7.82 (3H , M)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．５１（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、３．６７（２Ｈ，ｓ）、３．７７（３Ｈ，ｓ）、４．４９（２Ｈ，ｄ，Ｊ＝６．４Ｈｚ）、４．７５（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．８３−６．８６（２Ｈ，ｍ）、６．９５（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）、７．１２（１Ｈ，ｂｒ）、７．１９（２Ｈ，ｄ，Ｊ＝８．０Ｈｚ）、７．５２（２Ｈ，ｄ，Ｊ＝８．０Ｈｚ） Production Example 10
Instead of benzylamine, N- (4-trifluoromethylbenzyl) -2- (3-methoxy-4- (2-propynyloxy) was used in the same manner as in Production Example 3, using 4-trifluoromethylbenzylamine. ) Phenylthio) acetamide (hereinafter referred to as the present compound 10) 0.20 g was obtained.
Compound 10 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.51 (1H, t, J = 2.4 Hz), 3.67 (2H, s), 3.77 (3H, s), 4. 49 (2H, d, J = 6.4 Hz), 4.75 (2H, d, J = 2.4 Hz), 6.83-6.86 (2H, m), 6.95 (1H, d, J = 8.4 Hz), 7.12 (1H, br), 7.19 (2H, d, J = 8.0 Hz), 7.52 (2H, d, J = 8.0 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．５３（１Ｈ，ｔ，Ｊ＝２．４Ｈｚ）、３．６２（２Ｈ，ｓ）、３．７６（３Ｈ，ｓ）、３．８０（３Ｈ，ｓ）、４．３６（２Ｈ，ｄ，Ｊ＝５．６Ｈｚ）、４．７４（２Ｈ，ｄ，Ｊ＝２．４Ｈｚ）、６．７８−６．８５（４Ｈ，ｍ）、６．９３（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）、６．９６（１Ｈ，ｂｒ）、７．０４（２Ｈ，ｄ，Ｊ＝８．８Ｈｚ） Production Example 11
Using 4-methoxybenzylamine instead of benzylamine, N- (4-methoxybenzyl) -2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetic acid in the same manner as in Production Example 3. 0.14 g of amide (hereinafter referred to as the present compound 11) was obtained.
Compound 11 of the present invention

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.53 (1H, t, J = 2.4 Hz), 3.62 (2H, s), 3.76 (3H, s), 3. 80 (3H, s), 4.36 (2H, d, J = 5.6 Hz), 4.74 (2H, d, J = 2.4 Hz), 6.78-6.85 (4H, m), 6.93 (1H, d, J = 8.4 Hz), 6.96 (1H, br), 7.04 (2H, d, J = 8.8 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．２４（３Ｈ，ｓ）、５．６２（１Ｈ，ｂｒ）、６．７９（１Ｈ，ｄ，Ｊ＝８．３Ｈｚ）、７．２６（１Ｈ，ｄｄ，Ｊ＝２．４Ｈｚ，８．３Ｈｚ）、７．３３（１Ｈ，ｄ，Ｊ＝２．４Ｈｚ） Next, production examples of production intermediates of the compound of the present invention are shown.
Reference production example 1
10.8 g of o-cresol and 26 g of sodium thiocyanate were added to 70 ml of methanol, and a mixture of 5.3 ml of bromine, 10.3 g of sodium bromide and 120 ml of methanol was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 7 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 12 g of 2-methyl-4-thiocyanatophenol.

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.24 (3H, s), 5.62 (1H, br), 6.79 (1H, d, J = 8.3 Hz), 7. 26 (1H, dd, J = 2.4 Hz, 8.3 Hz), 7.33 (1H, d, J = 2.4 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．１９（３Ｈ，ｓ）、３．２４（１Ｈ，ｓ）、４．８７（１Ｈ，ｍ）、６．６５（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）、７．０３（１Ｈ，ｄｄ，Ｊ＝２．０Ｈｚ，８．０Ｈｚ）、７．１１（１Ｈ，ｄ，Ｊ＝２．０Ｈｚ） Lithium sodium hydride (1.4 g) was added to THF (200 ml), and a mixture of 2-methyl-4-thiocyanatophenol (6.0 g) and THF (100 ml) was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 3 hours. Water and dilute hydrochloric acid were sequentially added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 4.6 g of 4-mercapto-2-methylphenol.

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.19 (3H, s), 3.24 (1H, s), 4.87 (1H, m), 6.65 (1H, d, J = 8.4 Hz), 7.03 (1H, dd, J = 2.0 Hz, 8.0 Hz), 7.11 (1H, d, J = 2.0 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：３．９４（３Ｈ，ｓ）、５．８５（１Ｈ，ｓ）、６．９５（１Ｈ，ｄ，Ｊ＝８．４Ｈｚ）、７．０６（１Ｈ，ｄ，Ｊ＝１．６Ｈｚ）、７．１１（１Ｈ，ｄｄ，Ｊ＝１．６Ｈｚ，８．４Ｈｚ） Reference production example 2
To a solution obtained by adding 24 g of o-methoxyphenol and 47 g of sodium thiocyanate to 100 ml of methanol, a mixture of 9.9 ml of bromine, 20 g of sodium bromide and 300 ml of methanol was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained solid was washed with hexane to obtain 12 g of 2-methoxy-4-thiocyanatophenol.

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 3.94 (3H, s), 5.85 (1H, s), 6.95 (1H, d, J = 8.4 Hz), 7. 06 (1H, d, J = 1.6 Hz), 7.11 (1H, dd, J = 1.6 Hz, 8.4 Hz)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：３．４１（１Ｈ，ｓ）、３．８５（３Ｈ，ｓ）、５．５９（１Ｈ，ｓ）、６．７８−７．８９（３Ｈ，ｍ） To 300 ml of THF was added 6.0 g of lithium sodium hydride, and a mixture of 23 g of 2-methoxy-4-thiocyanatophenol and 200 ml of THF was added dropwise at -5 to 0 ° C., and the mixture was stirred at room temperature for 2 hours. Water and dilute hydrochloric acid were sequentially added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 18 g of 4-mercapto-2-methoxyphenol.

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 3.41 (1H, s), 3.85 (3H, s), 5.59 (1H, s), 6.78-7.89 ( 3H, m)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．５２（１Ｈ，ｔ，Ｊ＝２．０Ｈｚ）、３．５８（２Ｈ，ｓ）、３．７１（３Ｈ，ｓ）、３．８７（３Ｈ，ｓ）、４．７５（２Ｈ，ｄ，Ｊ＝２．０Ｈｚ）、６．９５−７．０５（３Ｈ，ｍ） To 100 ml of acetonitrile, 5.0 g of 4-mercapto-2-methoxyphenol, 4.9 g of methyl bromoacetate and 10.5 g of cesium carbonate were added, and the mixture was stirred under reflux conditions for 1.5 hours. To the reaction mixture, 3.8 g of propargyl bromide and 10.5 g of cesium carbonate were added, and the mixture was stirred for 2 hours under reflux conditions. Ethyl acetate was added to the reaction mixture, the mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 9.3 g of methyl 2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetate.

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.52 (1H, t, J = 2.0 Hz), 3.58 (2H, s), 3.71 (3H, s); 87 (3H, s), 4.75 (2H, d, J = 2.0 Hz), 6.95-7.05 (3H, m)

¹Ｈ−ＮＭＲ（ＣＤＣｌ₃，ＴＭＳ）δ（ｐｐｍ）：２．５２（１Ｈ，ｔ，Ｊ＝２．０Ｈｚ）、３．６０（２Ｈ，ｓ）、３．８６（３Ｈ，ｓ）、４．７５（２Ｈ，ｄ，Ｊ＝２．０Ｈｚ）、６．９６−７．０７（３Ｈ，ｍ） To a mixed solution of 100 ml of THF and 50 ml of water were added 9.3 g of methyl 2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetate and 3.0 g of lithium hydroxide monohydrate. Stir for 4 hours. Dilute hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained solid was washed successively with hexane and MTBE to obtain 7.6 g of 2- (3-methoxy-4- (2-propynyloxy) phenylthio) acetic acid.

¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 2.52 (1H, t, J = 2.0 Hz), 3.60 (2H, s), 3.86 (3H, s), 4. 75 (2H, d, J = 2.0 Hz), 6.96-7.07 (3H, m)

Next, formulation examples are shown. In addition, a part represents a weight part.
Formulation Example 1
Each wettable powder is obtained by thoroughly crushing and mixing 50 parts of each of the compounds 1 to 11 of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic silicon hydroxide.

Formulation Example 2
20 parts of each of the compounds 1 to 11 of the present invention and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and finely pulverized by a wet pulverization method. 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and stirred to obtain each flowable preparation.

Formulation Example 3
Each powder agent is obtained by thoroughly pulverizing and mixing 2 parts of each of the compounds 1 to 11 of the present invention, 88 parts of kaolin clay and 10 parts of talc.

Formulation Example 4
Each emulsion is obtained by thoroughly mixing 5 parts of each of the compounds 1 to 11 of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.

Formulation Example 5
2 parts of each of the compounds 1 to 11 of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, and then kneaded well with water, granulated and dried Thus, each granule is obtained.

Formulation Example 6
10 parts of each of the compounds 1 to 11 of the present invention; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; .

Next, test examples show that the compounds of the present invention are useful for controlling plant diseases.
The control effect is obtained by visually observing the area of the lesion on the test plant at the time of the survey, and comparing the area of the lesion on the plant treated with the compound of the present invention and the area of the lesion on the untreated plant. evaluated.

Test example 1
A plastic pot was filled with sandy loam, seeded with tomato (variety: Ponterosa), and grown in a greenhouse for 20 days. Each of the compounds 1 to 11 of the present invention was made into a flowable formulation according to Formulation Example 6, and then diluted with water so that the concentration of the compound of the present invention was 500 ppm to prepare a test drug solution. This test chemical solution was sprayed on the foliage so that it sufficiently adhered to the leaf surface of the tomato seedling. After spraying, the diluted solution on the leaf surface was air-dried to the extent that it was dried, and sprayed with a water suspension (about 10000 / ml) of tomato epidemic zoospores (a rate of about 2 ml per plant). After that, this tomato seedling was cultivated for 1 day under conditions of 23 ° C and relative humidity of 90% or more, and further transferred to a greenhouse at 24 ° C in the daytime and 20 ° C in the nighttime for 4 days. did. The lesion area on the plant which processed this invention compounds 1-11 was 10% or less of the lesion area of an unprocessed plant.

Test example 2
A plastic pot was filled with sand loam, sown with grapes (variety: Berry A), and grown in a greenhouse for 40 days. Each of the compounds 1 to 11 of the present invention was made into a flowable formulation according to Formulation Example 6, and then diluted with water to a concentration of 500 ppm to prepare a diluted solution. The diluted solution was sprayed on the foliage so as to adhere well to the grape leaf surface. After spraying, the diluted solution on the leaf surface was air-dried to the extent that it was dried, and sprayed with a water suspension (about 10000 / ml) of zoosporangium of grape mildew (approx. 2 ml per plant). . After that, the grape seedlings were cultivated for 1 day under conditions of 23 ° C. and relative humidity of 90% or more, further transferred to a greenhouse at 24 ° C. in the daytime and 20 ° C. at night, and cultivated for 6 days. . The lesion area of the plant which processed this invention compounds 1-11 was 10% or less of the lesion area of an unprocessed plant.

Claims (4)

Formula (1)

[Where,
R ¹ is a hydrogen atom, halogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, C1-C6 haloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 Haloalkynyl group, C1-C6 alkoxy group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C1-C6 haloalkoxy group, (C1-C6 alkoxy) C1-C6 alkyl group, phenoxy C1-C6 alkyl group, Hydroxy C1-C6 alkyl group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C1-C6 alkylamino group, di (C1-C6 alkyl) amino group, formyl group, (C1-C6 alkyl) carbonyl group, C1-C6 alkoxy) carbonyl group, (C1-C6 alkoxy) imino 1-C6 alkyl group, benzyloxyimino C1-C6 alkyl group, phenyl group, phenoxy group, cyano group, amino group or nitro group (provided that the benzene ring in the phenoxy C1-C6 alkyl group, phenyl group and phenoxy group is halogenated) And optionally substituted with a group selected from an atom, a C1-C3 alkyl group and a C1-C3 alkoxy group),
R ² represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a cyano group or a nitro group,
Alternatively, R ¹ and R ² are taken together to form a C3-C6 alkylene group or a —CR ⁵⁰ ═CR ⁵¹ —CR ⁵² ═CR ⁵³ — group (R ⁵⁰ , R ⁵¹ , R ⁵² and R ⁵³ are independently Represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group or a C1-C3 haloalkyl group),
R ³ represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C4 alkenyl group, a C3-C6 alkynyl group or a C2-C4 cyanoalkyl group,
R ⁴ represents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C3-C4 alkenyloxy group or a C3-C4 alkynyloxy group,
R ⁵ represents a hydrogen atom, a fluorine atom or a C1-C3 alkyl group. ]
An amide compound represented by R ¹ is a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group, R ² is a hydrogen atom, a halogen atom or a C1-C6 alkyl group, or R ¹ and R ² Together are a C3-C6 alkylene group or a —CH═CH—CH═CH— group, R ³ is a C3-C6 alkynyl group, R ⁴ is a C1-C4 alkoxy group, and R ⁵ is hydrogen. The amide compound according to claim 1, which is an atom.   A plant disease control agent comprising the amide compound according to claim 1 as an active ingredient.   A plant disease control method comprising treating an effective amount of the amide compound according to claim 1 or 2 to a plant or soil.