JP2009256263A - Amide compound and its use for plant disease control - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an amide compound having an excellent effectiveness of plant disease control. <P>SOLUTION: The plant disease controller comprises a compound represented by formula (1) as an active ingredient. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to an amide compound and its use for controlling plant diseases.

  Conventionally, many plant disease control agents have been developed and put into practical use. However, these plant disease control agents may not always show sufficient control efficacy.

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

〔式中、
Ｘ¹はフッ素原子又はメトキシ基を表し、
Ｘ²はメトキシ基、２−プロピニルオキシ基、アミノ基、モノメチルアミノ基又は２−プロピニルアミノ基を表し、
Ｚ¹は酸素原子又は硫黄原子を表し、
Ｅ¹はＡ¹−Ｃｙ¹で示される基又はＡ²−ＣＲ⁸Ｒ⁹Ｒ¹⁰で示される基を表し、
Ａ¹は単結合、ＣＨ₂基、ＣＨ（ＣＨ₃）基、Ｃ（ＣＨ₃）₂基、ＣＨ（ＣＨ₂ＣＨ₃）基、ＣＨ₂ＣＨ₂基、ＣＨ₂ＣＨ₂ＣＨ₂基又はＣ（ＣＨ₂ＣＨ₂）基、或いは、Ｃ１−Ｃ３ハロアルキル基、Ｃ２−Ｃ４アルケニル基及びＣ２−Ｃ４アルキニル基からなる群より選ばれる少なくとも１種の基で置換されたＣＨ₂基を表し、
Ａ²はＣＨ₂基、ＣＨ（ＣＨ₃）基、Ｃ（ＣＨ₃）₂基、ＣＨ（ＣＨ₂ＣＨ₃）基、或いは、Ｃ１−Ｃ３ハロアルキル基、Ｃ２−Ｃ４アルケニル基及びＣ２−Ｃ４アルキニル基からなる群より選ばれる少なくとも１種の基で置換されたＣＨ₂基を表し、
Ｃｙ¹は下記群［a-1］より選ばれる少なくとも１種の基で置換されていてもよいＣ３−Ｃ６シクロアルキル基、下記群［a-1］より選ばれる少なくとも１種の基で置換されていてもよいＣ３−Ｃ６シクロアルケニル基、下記群［a-1］より選ばれる少なくとも１種の基で置換されていてもよく、かつ環を形成するメチレンの１つがカルボニル基に置換されたＣ３−Ｃ６シクロアルキル基又は下記群［a-1］より選ばれる少なくとも１種の基で置換されていてもよいＣ３−Ｃ６ヒドロキシイミノシクロアルキル基を表し、
Ｒ⁸及びＲ⁹は独立してＣ１−Ｃ４アルキル基を表し、
Ｒ¹⁰は水素原子、Ｃ１−Ｃ４アルキル基、Ｃ２−Ｃ４アルケニル基、Ｃ２−Ｃ４アルキニル基、ハロゲン原子、ヒドロキシル基、Ｃ１−Ｃ６アルコキシ基、Ｃ３−Ｃ６アルケニルオキシ基、Ｃ１−Ｃ６ハロアルキル基、Ｃ２−Ｃ６ハロアルコキシ基、Ｃ１−Ｃ３アルキルチオ基、ヒドロキシＣ１−Ｃ６アルキル基、Ｃ２−Ｃ４アルキルカルボニルオキシ基、（Ｃ１−Ｃ３アルキルアミノ）Ｃ１−Ｃ６アルキル基、（ジ（Ｃ１−Ｃ３アルキル）アミノ）Ｃ１−Ｃ６アルキル基、メルカプト基、Ｃ１−Ｃ３アルキルスルホニル基又はＮＲ¹¹Ｒ¹²基〔式中、Ｒ¹¹及びＲ¹²は独立して水素原子又はＣ１−Ｃ４アルキル基を表す。〕を表す。
群［a-1］：
ハロゲン原子、Ｃ１−Ｃ４アルキル基、Ｃ２−Ｃ４アルケニル基、Ｃ２−Ｃ４アルキニル基、ヒドロキシル基、Ｃ１−Ｃ６アルコキシ基、Ｃ３−Ｃ６アルケニルオキシ基、Ｃ１−Ｃ６ハロアルキル基、Ｃ１−Ｃ６ハロアルコキシ基、Ｃ１−Ｃ３アルキルチオ基、環を形成する同一炭素原子との２重結合を形成するＣ１−Ｃ３アルキリデン基、ヒドロキシＣ１−Ｃ６アルキル基、Ｃ２−Ｃ４アルキルカルボニルオキシ基、（Ｃ１−Ｃ３アルキルアミノ）Ｃ１−Ｃ６アルキル基、（ジ（Ｃ１−Ｃ３アルキル）アミノ）Ｃ１−Ｃ６アルキル基、メルカプト基、ホルミル基、Ｃ１−Ｃ３アルキルスルホニル基又はＮＲ¹³Ｒ¹⁴基〔式中、Ｒ¹³及びＲ¹⁴は独立して水素原子又はＣ１−Ｃ４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場合もある。）を含有する植物病害防除剤（以下、本発明防除剤と記す場合もある。）、本発明化合物の有効量を植物又は土壌に施用することを特徴とする植物病害の防除方法を提供する。 As a result of studies to find a compound having an excellent plant disease control effect, the present inventors have found that an amide compound represented by the following formula (1) has an excellent plant disease control effect, leading to the present invention. It was.
That is, the present invention provides the formula (1)

[Where,
X ¹ represents a fluorine atom or a methoxy group,
X ² represents a methoxy group, 2-propynyloxy group, amino group, monomethylamino group or 2-propynylamino group,
Z ¹ represents an oxygen atom or a sulfur atom,
E ¹ represents a group represented by A ¹ -Cy ¹ or a group represented by A ² -CR ⁸ R ⁹ R ¹⁰ ;
A ¹ is a single bond, CH ₂ group, CH (CH ₃ ) group, C (CH ₃ ) ₂ group, CH (CH ₂ CH ₃ ) group, CH ₂ CH ₂ group, CH ₂ CH ₂ CH ₂ group or C ( A CH ₂ CH ₂ ) group, or a CH ₂ group substituted with at least one group selected from the group consisting of a C1-C3 haloalkyl group, a C2-C4 alkenyl group and a C2-C4 alkynyl group,
A ² is a CH ₂ group, a CH (CH ₃ ) group, a C (CH ₃ ) ₂ group, a CH (CH ₂ CH ₃ ) group, or a C1-C3 haloalkyl group, a C2-C4 alkenyl group, and a C2-C4 alkynyl group. Represents a CH ₂ group substituted with at least one group selected from the group consisting of:
Cy ¹ is substituted with at least one group selected from the following group [a-1], a C3-C6 cycloalkyl group optionally substituted with at least one group selected from the following group [a-1]. A C3-C6 cycloalkenyl group which may be substituted, C3 which may be substituted with at least one group selected from the following group [a-1], and one of the methylenes forming the ring is substituted with a carbonyl group A -C6 cycloalkyl group or a C3-C6 hydroxyiminocycloalkyl group optionally substituted with at least one group selected from the following group [a-1],
R ⁸ and R ⁹ independently represent a C1-C4 alkyl group,
R ¹⁰ is a hydrogen atom, C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4 alkynyl group, halogen atom, hydroxyl group, C1-C6 alkoxy group, C3-C6 alkenyloxy group, C1-C6 haloalkyl group, C2 -C6 haloalkoxy group, C1-C3 alkylthio group, hydroxy C1-C6 alkyl group, C2-C4 alkylcarbonyloxy group, (C1-C3 alkylamino) C1-C6 alkyl group, (di (C1-C3 alkyl) amino) C1-C6 alkyl group, mercapto group, C1-C3 alkylsulfonyl group or NR ¹¹ R ¹² group [wherein R ¹¹ and R ¹² independently represent a hydrogen atom or a C1-C4 alkyl group. ] Is represented.
Group [a-1]:
Halogen atom, C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4 alkynyl group, hydroxyl group, C1-C6 alkoxy group, C3-C6 alkenyloxy group, C1-C6 haloalkyl group, C1-C6 haloalkoxy group, C1-C3 alkylthio group, C1-C3 alkylidene group forming a double bond with the same carbon atom forming the ring, hydroxy C1-C6 alkyl group, C2-C4 alkylcarbonyloxy group, (C1-C3 alkylamino) C1 -C6 alkyl group, (di (C1-C3 alkyl) amino) C1-C6 alkyl group, mercapto group, formyl group, C1-C3 alkylsulfonyl group or NR ¹³ R ¹⁴ group [wherein R ¹³ and R ¹⁴ are independently Represents a hydrogen atom or a C1-C4 alkyl group. ]]
A plant disease control agent (hereinafter sometimes referred to as the present invention control agent) containing an amide compound represented by formula (hereinafter also referred to as the present invention compound), and an effective amount of the present compound as plant or soil The present invention provides a method for controlling plant diseases, which is characterized by applying to the plant.

  According to the present invention, plant diseases can be controlled.

In the present invention,
C1-C3 haloalkyl group represented by A ^1, in the CH ₂ group substituted with at least one group selected from the group consisting of C2-C4 alkenyl and C2-C4 alkynyl group,
C1-C3 haloalkyl group includes a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, a trichloromethyl group, a dichlorofluoromethyl group, a chlorodifluoromethyl group, 1,1-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-fluoroethyl group, 3-fluoropropyl group, 1-chloroethyl group, etc.
Examples of the C2-C4 alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, and 3-butenyl group.
Examples of the C2-C4 alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group and 3-butynyl group,

C1-C3 haloalkyl group represented by A ^2, the CH ₂ groups substituted with at least one group selected from the group consisting of C2-C4 alkenyl and C2-C4 alkynyl group,
The C1-C3 haloalkyl group includes a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, a trichloromethyl group, a dichlorofluoromethyl group, a chlorodifluoromethyl group, 1 , 1-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-fluoroethyl group, 3-fluoropropyl group, 1-chloroethyl group, etc.
Examples of the C2-C4 alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, and 3-butenyl group.
Examples of the C2-C4 alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group and 3-butynyl group,

Examples of the C1-C4 alkyl group represented by R ⁸ include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.
Examples of the C1-C4 alkyl group represented by R ⁹ include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.
Examples of the C1-C4 alkyl group represented by R ¹⁰ include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.
Examples of the C2-C4 alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, and 3-butenyl group.
Examples of the C2-C4 alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group and 3-butynyl group,
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
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, a tert-butoxy group, a pentyloxy group, an isopentyloxy group, and a hexyloxy group. Are mentioned,
As C3-C6 alkenyloxy group, 2-propenyloxy group, 1-methyl-2-propenyloxy group, 2-methyl-2-propenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 2-hexenyloxy group And 5-hexenyloxy group, etc.
As C1-C6 haloalkyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, trichloromethyl group, chlorofluoromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2 , 2,2-trifluoroethyl group and 6,6,6-trifluorohexyl group, etc.
The C2-C6 haloalkoxy group includes trifluoromethoxy group, difluoromethoxy group, bromodifluoromethoxy group, chlorodifluoromethoxy group, fluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2 -Tetrafluoroethoxy group, 5-chloropentyloxy group, 4-fluoroisopentyloxy group, 2,2-dichlorohexyloxy group, etc.
Examples of the C1-C3 alkylthio group include a methylthio group, an ethylthio group, a 1-methylethylthio group, and a propylthio 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 2-hydroxypropyl group. As the C2-C4 alkylcarbonyloxy group, Acetoxy group, ethylcarbonyloxy group, 1-methylethylcarbonyloxy group, propylcarbonyloxy group and the like,
(C1-C3 alkylamino) As C1-C6 alkyl group, N-methylaminomethyl group, N-ethylaminomethyl group, 1- (N-methylamino) ethyl group, 2- (N-methylamino) ethyl group And 1- (N-ethylamino) ethyl group, etc.
(Di (C1-C3 alkyl) amino) C1-C6 alkyl group includes N, N-dimethylaminomethyl group, 1- (N, N-dimethylamino) ethyl group, 2- (N, N-dimethylamino). And an ethyl group and an N, N-diethylaminomethyl group, etc.
Examples of the C1-C3 alkylsulfonyl group include a methanesulfonyl group and an ethanesulfonyl group.
Examples of the C1-C4 alkyl group represented by R ¹¹ include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.
Examples of the C1-C4 alkyl group represented by R ¹² include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.

Represented by group [a-1],
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the C1-C4 alkyl group include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.
Examples of the C2-C4 alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, and 3-butenyl group.
Examples of the C2-C4 alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group and 3-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, a tert-butoxy group, a pentyloxy group, an isopentyloxy group, and a hexyloxy group. Are mentioned,
As C3-C6 alkenyloxy group, 2-propenyloxy group, 1-methyl-2-propenyloxy group, 2-methyl-2-propenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 2-hexenyloxy group And 5-hexenyloxy group, etc.
As C1-C6 haloalkyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, trichloromethyl group, chlorofluoromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2,2-difluoroethyl group, 2 , 2,2-trifluoroethyl group and 6,6,6-trifluorohexyl group, etc.
Examples of the C1-C6 haloalkoxy group include trifluoromethoxy group, difluoromethoxy group, bromodifluoromethoxy group, chlorodifluoromethoxy group, fluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2 -Tetrafluoroethoxy group, 5-chloropentyloxy group, 4-fluoroisopentyloxy group, 2,2-dichlorohexyloxy group, etc.
Examples of the C1-C3 alkylthio group include a methylthio group, an ethylthio group, a 1-methylethylthio group, and a propylthio group.
The C1-C3 alkylidene group that forms a double bond with the same carbon atom that forms a ring includes a methylene group that forms a double bond with the same carbon atom that forms a ring, and the same carbon atom that forms a ring. And an ethylidene group that forms a double bond, an isopropylidene group that forms a double bond with the same carbon atom that forms a ring, and a propylidene group that forms a double bond with the same carbon atom that forms a ring,
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 2-hydroxypropyl group.
Examples of the C2-C4 alkylcarbonyloxy group include an acetoxy group, an ethylcarbonyloxy group, a 1-methylethylcarbonyloxy group, and a propylcarbonyloxy group.
(C1-C3 alkylamino) As C1-C6 alkyl group, N-methylaminomethyl group, N-ethylaminomethyl group, 1- (N-methylamino) ethyl group, 2- (N-methylamino) ethyl group And 1- (N-ethylamino) ethyl group, etc.
(Di (C1-C3 alkyl) amino) C1-C6 alkyl group includes N, N-dimethylaminomethyl group, 1- (N, N-dimethylamino) ethyl group, 2- (N, N-dimethylamino). And an ethyl group and an N, N-diethylaminomethyl group, etc.
Examples of the C1-C3 alkylsulfonyl group include a methanesulfonyl group and an ethanesulfonyl group.

Examples of the C1-C4 alkyl group represented by R ¹³ include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.
Examples of the C1-C4 alkyl group represented by R ¹⁴ include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.

Indicated by Cy ¹ ,
The C3-C6 cycloalkyl group in the C3-C6 cycloalkyl group optionally substituted with at least one group selected from the group [a-1] includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Xyl group,
The C3-C6 cycloalkenyl group in the C3-C6 cycloalkenyl group optionally substituted with at least one group selected from the group [a-1] includes a 2-cyclopropenyl group, a 1-cyclobutenyl group, 2 -Cyclobutenyl group, 1-cyclopentenyl group, 2-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 2-cyclohexenyl group and 3-cyclohexenyl group,
The C3-C6 cycloalkyl group which may be substituted with at least one group selected from the group [a-1] and in which one of the methylenes forming the ring is substituted with a carbonyl group includes 2-oxocyclo Propyl group, 2-oxocyclobutyl group, 3-oxocyclobutyl group, 2-oxocyclopentyl group, 3-oxocyclopentyl group, 2-oxocyclohexyl group, 3-oxocyclohexyl group, 4-oxocyclohexyl group, etc. ,
The C3-C6 hydroxyiminocycloalkyl group in the C3-C6 hydroxyiminocycloalkyl group optionally substituted with at least one group selected from the group [a-1] is a 2-hydroxyiminocyclopropyl group, 2-hydroxyiminocyclobutyl group, 3-hydroxyiminocyclobutyl group, 2-hydroxyiminocyclopentyl group, 3-hydroxyiminocyclopentyl group, 2-hydroxyiminocyclohexyl group, 3-hydroxyiminocyclohexyl group and 4-hydroxyiminocyclohexyl group Etc.

Specific examples of the group represented by A ¹ -Cy ¹ include, for example,
A cyclopropyl group, a 2,2,3,3-tetramethylcyclopropyl group;
A cyclobutyl group;
Cyclopentyl group, 2-methylcyclopentyl group, 2-hydroxycyclopentyl group, 2-chlorocyclopentyl group, 2-bromocyclopentyl group, 2,2-dimethylcyclopentyl group, 2-fluoro-2-methylcyclopentyl group, 2-chloro-2 -Methylcyclopentyl group, 2-hydroxy-2-methylcyclopentyl group, 2,2-difluorocyclopentyl group, 3-methylcyclopentyl group;
Cyclohexyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2-trifluoromethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 2-fluoro-2-methyl Cyclohexyl group, 2-chloro-2-methylcyclohexyl group, 2-hydroxy-2-methylcyclohexyl group, 2,2-difluorocyclohexyl group, 2,3-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 2-ethyl A cyclohexyl group, 2-chlorocyclohexyl group, 2-fluorocyclohexyl group, 2-bromocyclohexyl group, 2-iodocyclohexyl group, 2-hydroxycyclohexyl group;

Cyclopropylmethyl group, (1-methylcyclopropyl) methyl group, (2-methylcyclopropyl) methyl group, (1-hydroxycyclopropyl) methyl group, (2-hydroxycyclopropyl) methyl group, (2,2, 3,3-tetramethylcyclopropyl) methyl group, (1-fluorocyclopropyl) methyl group, (1-chlorocyclopropyl) methyl group;
Cyclobutylmethyl, (1-methylcyclobutyl) methyl, (2-methylcyclobutyl) methyl, (3-methylcyclobutyl) methyl, (1-hydroxycyclobutyl) methyl, (2-hydroxycyclo) (Butyl) methyl group, (3-hydroxycyclobutyl) methyl group, (1-fluorocyclobutyl) methyl group, (1-chlorocyclobutyl) methyl group;
Cyclopentylmethyl group, (1-methylcyclopentyl) methyl group, (2-methylcyclopentyl) methyl group, (3-methylcyclopentyl) methyl group, (1-hydroxycyclopentyl) methyl group, (2-hydroxycyclopentyl) methyl group, 3-hydroxycyclopentyl) methyl group, (1-fluorocyclopentyl) methyl group, (1-chlorocyclopentyl) methyl group;
Cyclohexylmethyl group, (1-methylcyclohexyl) methyl group, (2-methylcyclohexyl) methyl group, (3-methylcyclohexyl) methyl group, (4-methylcyclohexyl) methyl group, (2,3-dimethylcyclohexyl) methyl group , (1-hydroxycyclohexyl) methyl group, (2-hydroxycyclohexyl) methyl group, (3-hydroxycyclohexyl) methyl group, (4-hydroxycyclohexyl) methyl group, (1-fluorocyclohexyl) methyl group, (1-chloro (Cyclohexyl) methyl group, (1-ethynylcyclohexyl) methyl group, (2-fluorocyclohexyl) methyl group, (2-chlorocyclohexyl) methyl group;

1- (cyclopropyl) ethyl group, 1- (1-methylcyclopropyl) ethyl group, 1- (2-methylcyclopropyl) ethyl group, 1- (1-hydroxycyclopropyl) ethyl group, 1- (2- Hydroxycyclopropyl) ethyl group, 1- (2,2,3,3-tetramethylcyclopropyl) ethyl group, 1- (1-fluorocyclopropyl) ethyl group, 1- (1-chlorocyclopropyl) ethyl group;
1- (cyclobutyl) ethyl group, 1- (1-methylcyclobutyl) ethyl group, 1- (2-methylcyclobutyl) ethyl group, 1- (3-methylcyclobutyl) ethyl group, 1- (1-hydroxy Cyclobutyl) ethyl group, 1- (2-hydroxycyclobutyl) ethyl group, 1- (3-hydroxycyclobutyl) ethyl group, 1- (1-fluorocyclobutyl) ethyl group, 1- (1-chlorocyclobutyl) ) Ethyl group;
1- (cyclopentyl) ethyl group, 1- (1-methylcyclopentyl) ethyl group, 1- (2-methylcyclopentyl) ethyl group, 1- (3-methylcyclopentyl) ethyl group, 1- (1-hydroxycyclopentyl) ethyl A group, 1- (2-hydroxycyclopentyl) ethyl group, 1- (3-hydroxycyclopentyl) ethyl group, 1- (1-fluorocyclopentyl) ethyl group, 1- (1-chlorocyclopentyl) ethyl group;
1- (cyclohexyl) ethyl group, 1- (1-methylcyclohexyl) ethyl group, 1- (2-methylcyclohexyl) ethyl group, 1- (3-methylcyclohexyl) ethyl group, 1- (4-methylcyclohexyl) ethyl Group, 1- (2,3-dimethylcyclohexyl) ethyl group, 1- (1-hydroxycyclohexyl) ethyl group, 1- (2-hydroxycyclohexyl) ethyl group, 1- (3-hydroxycyclohexyl) ethyl group, 1- (4-hydroxycyclohexyl) ethyl group, 1- (1-fluorocyclohexyl) ethyl group, 1- (1-chlorocyclohexyl) ethyl group, 1- (1-ethynylcyclohexyl) ethyl group, 1- (2-fluorocyclohexyl) An ethyl group, 1- (2-chlorocyclohexyl) ethyl group;

1-methyl-1-cyclopropylethyl group, 1-methyl-1-cyclobutylethyl group, 1-methyl-1- (1-hydroxycyclobutyl) ethyl group, 1-methyl-1- (1-fluorocyclobutyl ) Ethyl group, 1-methyl-1-cyclopentylethyl group, 1-methyl-1- (1-hydroxycyclopentyl) ethyl group, 1-methyl-1- (1-fluorocyclopentyl) ethyl group, 1-methyl-1- A cyclohexylethyl group, a 1-methyl-1- (1-hydroxycyclohexyl) ethyl group, a 1-methyl-1- (1-fluorocyclohexyl) ethyl group,
(1-hydroxymethylcyclopropyl) methyl group, (1-hydroxymethylcyclobutyl) methyl group, (1-hydroxymethylcyclopentyl) methyl group, (1-hydroxymethylcyclohexyl) methyl group, (1-cyclohexenyl) methyl group , (2-cyclohexenyl) methyl group, (3-cyclohexenyl) methyl group, (1-cyclopentenyl) methyl group, (2-cyclopentenyl) methyl group, (1-dimethylaminocyclopropyl) methyl group, (1 -Dimethylaminocyclobutyl) methyl group, (1-dimethylaminocyclopentyl) methyl group, (1-dimethylaminocyclohexyl) methyl group,
(1-acetoxycyclopropyl) methyl group, (1-acetoxycyclobutyl) methyl group, (1-acetoxycyclopentyl) methyl group, (1-acetoxycyclohexyl) methyl group,
(2-acetoxycyclohexyl) methyl group, 2-cyclohexenyl group, 3-cyclohexenyl group, 2-methoxycyclopropyl group, 2-methoxycyclobutyl group, 2-methoxycyclopentyl group, 2-methoxycyclohexyl group, 3-methoxy Cyclohexyl group, 4-methoxycyclohexyl group, (1-methoxycyclohexyl) methyl group, (2-methoxycyclohexyl) methyl group, 2-acetoxycyclobutyl group, 2-acetoxycyclopentyl group, 2-acetoxycyclohexyl group, 2-methylthiocyclo Butyl, 2-methylthiocyclopentyl, 2-methylthiocyclohexyl, 2-aminocyclobutyl, 2-aminocyclopentyl, 2-aminocyclohexyl, 2-dimethylaminocyclobutyl, 2-dimethyla Nocyclopentyl group, 2-dimethylaminocyclohexyl group, 2-trifluoromethylcyclobutyl group, 2-trifluoromethylcyclopentyl group, 2-trifluoromethylcyclohexyl group, 2-hydroxymethylcyclobutyl group, 2-hydroxymethylcyclopentyl group 2-hydroxymethylcyclohexyl group, 2-methylenecyclohexyl group, 3-methylenecyclohexyl group, 4-methylenecyclohexyl group, 2-methylenecyclopentyl group, 3-methylenecyclopentyl group, 2-oxocyclohexyl group, 3-oxocyclohexyl group, Examples include 4-oxocyclohexyl group, 2-oxocyclopentyl group, 3-oxocyclopentyl group, 2-hydroxyiminocyclohexyl group and 2-hydroxyiminocyclopentyl group.

Specific examples of the group represented by A ² —CR ⁸ R ⁹ R ¹⁰ include 2-methylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1,2,2- Trimethylpropyl group, 1,1,2,2-tetramethylpropyl group, 2-methyl-2-hydroxypropyl group, 1,2-dimethyl-2-hydroxypropyl group, 2-chloro-1,2-dimethylpropyl group 2-chloro-2-methylpropyl group, 1,2-dimethylbutyl group, 2,2-dimethyl-3-hydroxypropyl group, 3-hydroxy-1,2,2-trimethylpropyl group and the like.

As an aspect of this invention compound, the following are mentioned, for example.
An amide compound in which Z ¹ is an oxygen atom in formula (1);
An amide compound in which X ¹ is a fluorine atom in formula (1);
An amide compound in which X ¹ is a methoxy group in formula (1);
An amide compound in which X ² is a methoxy group or a 2-propynyl group in formula (1);
An amide compound in which X ² is an amino group, a monomethylamino group or a 2-propynylamino group in formula (1);
An amide compound in which X ² is a methoxy group in formula (1);
An amide compound in which X ² is a 2-propynyloxy group in formula (1);
An amide compound in which X ² is an amino group in formula (1);
An amide compound in which X ² is a monomethylamino group in formula (1);
An amide compound represented by formula (1), wherein X ² is a 2-propynylamino group;

An amide compound in which X ¹ is a fluorine atom and X ² is a methoxy group or a 2-propynyl group in formula (1);
An amide compound in which X ¹ is a fluorine atom and X ² is an amino group, a monomethylamino group or a 2-propynylamino group in the formula (1);
An amide compound in which X ¹ is a fluorine atom and X ² is a methoxy group in formula (1);
An amide compound in which X ¹ is a fluorine atom and X ² is a 2-propynyloxy group in formula (1);
An amide compound in which X ¹ is a fluorine atom and X ² is an amino group in formula (1);
An amide compound in which X ¹ is a fluorine atom and X ² is a monomethylamino group in formula (1);
An amide compound in which X ¹ is a fluorine atom and X ² is a 2-propynylamino group in formula (1);

An amide compound in which X ¹ is a methoxy group and X ² is a methoxy group or a 2-propynyloxy group in formula (1);
An amide compound in which X ¹ is a methoxy group and X ² is an amino group, a monomethylamino group or a 2-propynylamino group in the formula (1);
An amide compound in which X ¹ is a methoxy group and X ² is a methoxy group in formula (1);
An amide compound in which X ¹ is a methoxy group and X ² is a 2-propynyloxy group in formula (1);
An amide compound in which X ¹ is a methoxy group and X ² is an amino group in formula (1);
An amide compound in which X ¹ is a methoxy group and X ² is a monomethylamino group in formula (1);
An amide compound in which X ¹ is a methoxy group and X ² is a 2-propynylamino group in formula (1);

An amide compound in which E ¹ is a group represented by A ¹ -Cy ¹ in formula (1);
An amide compound represented by formula (1), wherein E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond, a CH ₂ group or a CH (CH ₃ ) group;
An amide compound in which E ¹ is a group represented by A ¹ -Cy ¹ and A ¹ is a single bond in formula (1);
An amide compound in which E ¹ is a group represented by A ¹ -Cy ¹ and A ¹ is a CH ₂ group in formula (1);
An amide compound represented by formula (1), wherein E ¹ is a group represented by A ¹ -Cy ¹ and A ¹ is a CH (CH ₃ ) group;
In the formula (1), E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ may be substituted with at least one group selected from the group [a-1]. An amide compound as a group;
In Formula (1), E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a hydroxyl group, C1- C3 optionally substituted by at least one group selected from the group consisting of a C6 alkoxy group, a C1-C3 alkylidene group forming a double bond with the same carbon atom forming the ring, and a hydroxy C1-C6 alkyl group An amide compound being a C6 cycloalkyl group;
In Formula (1), E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is substituted with at least one group selected from the group consisting of a halogen atom, a C1-C4 alkyl group and a hydroxyl group. An amide compound which may be a C3-C6 cycloalkyl group;
In the formula (1), E ¹ is 2-methylcyclopentyl group, 2-fluorocyclopentyl group, 2-chlorocyclopentyl group, 2-hydroxycyclopentyl group, 2-methylcyclohexyl group, 2-fluorocyclohexyl group, 2-chlorocyclohexyl. Group, 2-hydroxycyclohexyl group, cyclobutylmethyl group, cyclopentylmethyl group, cyclohexylmethyl group, (1-hydroxycyclobutyl) methyl group, (1-hydroxycyclopentyl) methyl group, (1-hydroxycyclohexyl) methyl group, 1 -Cyclobutylethyl group, 1-cyclopentylethyl group, 1-cyclohexylethyl group, 1- (1-hydroxycyclobutyl) ethyl group, 1- (1-hydroxycyclopentyl) ethyl group or 1- (1-hydroxycyclohexyl) Amide compound is a methyl group;
In formula (1), E ¹ is a 2-methylcyclopentyl group, 2-fluorocyclopentyl group, 2-chlorocyclopentyl group, 2-hydroxycyclopentyl group, 2-methylcyclohexyl group, 2-fluorocyclohexyl group, 2-chlorocyclohexyl group. Or an amide compound which is a 2-hydroxycyclohexyl group;
In the formula (1), E ¹ is a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a (1-hydroxycyclobutyl) methyl group, a (1-hydroxycyclopentyl) methyl group, a (1-hydroxycyclohexyl) methyl group, 1-cyclobutylethyl group, 1-cyclopentylethyl group, 1-cyclohexylethyl group, 1- (1-hydroxycyclobutyl) ethyl group, 1- (1-hydroxycyclopentyl) ethyl group or 1- (1-hydroxycyclohexyl) An amide compound which is an ethyl group;

An amide compound represented by formula (1), wherein E ¹ is a 2-methylcyclohexyl group;
An amide compound represented by formula (1), wherein E ¹ is a 2-chlorocyclohexyl group;
An amide compound represented by formula (1), wherein E ¹ is a cyclohexylmethyl group;
An amide compound represented by formula (1), wherein E ¹ is a 1-cyclohexylethyl group;
An amide compound represented by formula (1), wherein E ¹ is a (1-hydroxycyclohexyl) methyl group;
An amide compound represented by formula (1), wherein E ¹ is a 1- (1-hydroxycyclohexyl) ethyl group;
An amide compound represented by formula (1), wherein E ¹ is a cyclobutylmethyl group;
An amide compound in which E ¹ is a 1-cyclobutylethyl group in formula (1);
An amide compound represented by formula (1), wherein E ¹ is a (1-hydroxycyclobutyl) methyl group;
An amide compound represented by formula (1), wherein E ¹ is a 1- (1-hydroxycyclobutyl) ethyl group;

An amide compound in which E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ in formula (1);
In formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or a C (CH ₃ ) ₂ group. ;
An amide compound in which E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ and A ² is a CH ₂ group in formula (1);
An amide compound in which E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ and A ² is a CH (CH ₃ ) group in formula (1);
An amide compound in which E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ and A ² is a C (CH ₃ ) ₂ group in formula (1);
An amide compound in which E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ in formula (1), R ⁸ is a methyl group, and R ⁹ is a methyl group;
In Formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, a CH (CH ₃ ) group or a C (CH ₃ ) ₂ group, and R ^An amide compound in which ⁸ is a methyl group and R ⁹ is a methyl group;
In formula (1), an amide in which E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, R ⁸ is a methyl group, and R ⁹ is a methyl group Compound;
In the formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, R ⁸ is a methyl group, and R ⁹ is a methyl group. An amide compound;
In formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, R ⁸ is a methyl group, and R ⁹ is methyl. An amide compound as a group;

In Formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, a hydroxyl group, a C1-C6 alkoxy group, C1 -C3 alkylthio group, hydroxy C1-C6 alkyl group, (C1-C3 alkylamino) C1-C6 alkyl group, (di (C1-C3 alkyl) amino) C1-C6 alkyl group, mercapto group, C1-C3 alkylsulfonyl group or NR ¹¹ R ¹² group wherein, R ¹¹ and R ¹² represents a hydrogen atom or a C1-C4 alkyl group independently. An amide compound;
An amide compound in which E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ in formula (1), and R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In the formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, a hydroxyl group Group, C1-C6 alkoxy group, C1-C3 alkylthio group, hydroxy C1-C6 alkyl group, (C1-C3 alkylamino) C1-C6 alkyl group, (di (C1-C3 alkyl) amino) C1-C6 alkyl group, Mercapto group, C1-C3 alkylsulfonyl group or NR ¹¹ R ¹² group [wherein R ¹¹ and R ¹² independently represent a hydrogen atom or a C1-C4 alkyl group. An amide compound;
In the formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, a hydroxyl group An amide compound as a group;
In formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom Atom, hydroxyl group, C1-C6 alkoxy group, C1-C3 alkylthio group, hydroxy C1-C6 alkyl group, (C1-C3 alkylamino) C1-C6 alkyl group, (di (C1-C3 alkyl) amino) C1-C6 An alkyl group, a mercapto group, a C1-C3 alkylsulfonyl group or an NR ¹¹ R ¹² group [wherein R ¹¹ and R ¹² independently represent a hydrogen atom or a C1-C4 alkyl group; An amide compound;
In formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom An amide compound that is an atom or a hydroxyl group;
In Formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, Halogen atom, hydroxyl group, C1-C6 alkoxy group, C1-C3 alkylthio group, hydroxy C1-C6 alkyl group, (C1-C3 alkylamino) C1-C6 alkyl group, (di (C1-C3 alkyl) amino) C1- C6 alkyl group, mercapto group, C1-C3 alkylsulfonyl group or NR ¹¹ R ¹² group [wherein R ¹¹ and R ¹² independently represent a hydrogen atom or a C1-C4 alkyl group. An amide compound;
In Formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, An amide compound which is a halogen atom or a hydroxyl group;
In the formula (1), E ¹ is a 2-methylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, a 1,2,2-trimethylpropyl group, a 2-methyl-2-hydroxypropyl group. Or an amide compound which is a 1,2-dimethyl-2-hydroxypropyl group;

An amide compound in which Z ¹ is an oxygen atom and E ¹ is a group represented by A ¹ -Cy ¹ in formula (1);
An amide compound represented by formula (1), wherein Z ¹ is an oxygen atom, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond, a CH ₂ group or a CH (CH ₃ ) group;
An amide compound in which Z ¹ is an oxygen atom in formula (1), E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond;
An amide compound represented by formula (1), wherein Z ¹ is an oxygen atom, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH ₂ group;
An amide compound represented by formula (1), wherein Z ¹ is an oxygen atom, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH (CH ₃ ) group;
In Formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is substituted with at least one group selected from the group [a-1]. An amide compound which may be a C3-C6 cycloalkyl group;
In Formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is at least selected from the group consisting of a halogen atom, a C1-C4 alkyl group and a hydroxyl group. An amide compound which is a C3-C6 cycloalkyl group optionally substituted by one group;
In the formula (1), Z ¹ is an oxygen atom, and E ¹ is a 2-methylcyclopentyl group, 2-fluorocyclopentyl group, 2-chlorocyclopentyl group, 2-hydroxycyclopentyl group, 2-methylcyclohexyl group, 2-fluoro An amide compound which is a cyclohexyl group, a 2-chlorocyclohexyl group or a 2-hydroxycyclohexyl group;
In formula (1), Z ¹ is an oxygen atom, E ¹ is a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a (1-hydroxycyclobutyl) methyl group, a (1-hydroxycyclopentyl) methyl group, ( 1-hydroxycyclohexyl) methyl group, 1-cyclobutylethyl group, 1-cyclopentylethyl group, 1-cyclohexylethyl group, 1- (1-hydroxycyclobutyl) ethyl group, 1- (1-hydroxycyclopentyl) ethyl group or An amide compound which is a 1- (1-hydroxycyclohexyl) ethyl group;

An amide compound in which Z ¹ is an oxygen atom and E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ in formula (1);
In the formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or C (CH ₃ ) Amide compound which is _two groups;
An amide compound in which Z ¹ is an oxygen atom in formula (1), E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group;
An amide compound in which, in formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH (CH ₃ ) group;
An amide compound represented by formula (1), wherein Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ⁸ is a methyl group, and R ⁹ is a methyl group;
In the formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or C (CH ₃ ) an amide compound having _two groups, R ⁸ is a methyl group, and R ⁹ is a methyl group;
In Formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, R ⁸ is a methyl group, An amide compound in which R ⁹ is a methyl group;
In the formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, and R ⁸ is a methyl group. An amide compound wherein R ⁹ is a methyl group;
In the formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, and R ⁸ is methyl. An amide compound wherein R ⁹ is a methyl group;
In the formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, a hydroxyl group An amide compound;
In formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, R ¹⁰ is a hydrogen atom, C 1- An amide compound which is a C4 alkyl group, a halogen atom, or a hydroxyl group;
In Formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, and R ¹⁰ is a hydrogen atom. An amide compound which is a C1-C4 alkyl group, a halogen atom or a hydroxyl group;
In the formula (1), Z ¹ is an oxygen atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, and R ¹⁰ is hydrogen. An amide compound which is an atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In the formula (1), Z ¹ is an oxygen atom, and E ¹ is a 2-methylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1,2,2-trimethylpropyl group, 2 An amide compound which is a methyl-2-hydroxypropyl group or a 1,2-dimethyl-2-hydroxypropyl group;

An amide compound in which X ¹ is a fluorine atom and E ¹ is a group represented by A ¹ -Cy ¹ in formula (1);
An amide compound represented by formula (1), wherein X ¹ is a fluorine atom, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond, a CH ₂ group or a CH (CH ₃ ) group;
An amide compound in which, in formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond;
An amide compound represented by formula (1), wherein X ¹ is a fluorine atom, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH ₂ group;
An amide compound represented by formula (1), wherein X ¹ is a fluorine atom, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH (CH ₃ ) group;
In Formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is substituted with at least one group selected from the group [a-1]. An amide compound which may be a C3-C6 cycloalkyl group;
In Formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is at least selected from the group consisting of a halogen atom, a C1-C4 alkyl group and a hydroxyl group. An amide compound which is a C3-C6 cycloalkyl group optionally substituted by one group;
In the formula (1), X ¹ is a fluorine atom, and E ¹ is a 2-methylcyclopentyl group, 2-fluorocyclopentyl group, 2-chlorocyclopentyl group, 2-hydroxycyclopentyl group, 2-methylcyclohexyl group, 2-fluoro An amide compound which is a cyclohexyl group, a 2-chlorocyclohexyl group or a 2-hydroxycyclohexyl group;
In the formula (1), X ¹ is a fluorine atom, E ¹ is a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a (1-hydroxycyclobutyl) methyl group, a (1-hydroxycyclopentyl) methyl group, 1-hydroxycyclohexyl) methyl group, 1-cyclobutylethyl group, 1-cyclopentylethyl group, 1-cyclohexylethyl group, 1- (1-hydroxycyclobutyl) ethyl group, 1- (1-hydroxycyclopentyl) ethyl group or An amide compound which is a 1- (1-hydroxycyclohexyl) ethyl group;

An amide compound in which X ¹ is a fluorine atom and E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ in formula (1);
In Formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or C (CH ₃ ) Amide compound which is _two groups;
An amide compound represented by formula (1), wherein X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group;
An amide compound in which X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH (CH ₃ ) group in formula (1);
In formula (1), an amide compound in which X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ⁸ is a methyl group, and R ⁹ is a methyl group ;
In the formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or C (CH ₃ ) an amide compound having _two groups, R ⁸ is a methyl group, and R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, R ⁸ is a methyl group, An amide compound in which R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, and R ⁸ is a methyl group. An amide compound wherein R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, and R ⁸ is methyl. An amide compound wherein R ⁹ is a methyl group;
In the formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, a hydroxyl group An amide compound;
In the formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, R ¹⁰ is a hydrogen atom, C 1− An amide compound which is a C4 alkyl group, a halogen atom, or a hydroxyl group;
In the formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, and R ¹⁰ is a hydrogen atom. An amide compound which is a C1-C4 alkyl group, a halogen atom or a hydroxyl group;
In the formula (1), X ¹ is a fluorine atom, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, and R ¹⁰ is hydrogen. An amide compound which is an atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In the formula (1), X ¹ is a fluorine atom, and E ¹ is a 2-methylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1,2,2-trimethylpropyl group, 2 An amide compound which is a methyl-2-hydroxypropyl group or a 1,2-dimethyl-2-hydroxypropyl group;

An amide compound in which X ² is a 2-propynyloxy group and E ¹ is a group represented by A ¹ -Cy ¹ in formula (1);
In Formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond, a CH ₂ group or a CH (CH ₃ ) group. An amide compound;
An amide compound in which, in formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond;
An amide compound represented by the formula (1), wherein X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH2 group;
An amide compound in which, in formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH (CH ₃ ) group;
In Formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is at least one group selected from the group [a-1]. An amide compound which is an optionally substituted C3-C6 cycloalkyl group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is a group consisting of a halogen atom, a C1-C4 alkyl group and a hydroxyl group. An amide compound which is a C3-C6 cycloalkyl group optionally substituted with at least one selected group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a 2-methylcyclopentyl group, a 2-fluorocyclopentyl group, a 2-chlorocyclopentyl group, a 2-hydroxycyclopentyl group, a 2-methylcyclohexyl group, An amide compound which is a 2-fluorocyclohexyl group, a 2-chlorocyclohexyl group or a 2-hydroxycyclohexyl group;
In the formula (1), X ² is a 2-propynyloxy group, and E ¹ is a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a (1-hydroxycyclobutyl) methyl group, or (1-hydroxycyclopentyl) methyl. Group, (1-hydroxycyclohexyl) methyl group, 1-cyclobutylethyl group, 1-cyclopentylethyl group, 1-cyclohexylethyl group, 1- (1-hydroxycyclobutyl) ethyl group, 1- (1-hydroxycyclopentyl) An amide compound which is an ethyl group or a 1- (1-hydroxycyclohexyl) ethyl group;

An amide compound in which X ² is a 2-propynyloxy group and E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ in formula (1);
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or An amide compound which is a C (CH ₃ ) ₂ group;
An amide compound represented by formula (1), wherein X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group;
An amide compound represented by formula (1), wherein X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH (CH ₃ ) group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ⁸ is a methyl group, and R ⁹ is a methyl group. An amide compound;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or An amide compound which is a C (CH ₃ ) ₂ group, R ⁸ is a methyl group, and R ⁹ is a methyl group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, and R ⁸ is a methyl group. An amide compound wherein R ⁹ is a methyl group;
In Formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, and R ⁸ An amide compound wherein is a methyl group and R ⁹ is a methyl group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, R ^An amide compound wherein ⁸ is a methyl group and R ⁹ is a methyl group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom An amide compound which is a hydroxyl group;
In Formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, and R ¹⁰ is a hydrogen atom. An amide compound which is a C1-C4 alkyl group, a halogen atom or a hydroxyl group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, R ¹⁰ An amide compound in which is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, R ^An amide compound in which ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In the formula (1), X ² is a 2-propynyloxy group, E ¹ is a 2-methylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, a 1,2,2-trimethylpropyl group An amide compound which is a group, 2-methyl-2-hydroxypropyl group or 1,2-dimethyl-2-hydroxypropyl group;

An amide compound in which X ² is an amino group and E ¹ is a group represented by A ¹ -Cy ¹ in formula (1);
An amide compound represented by formula (1), wherein X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond, a CH ₂ group or a CH (CH ₃ ) group;
An amide compound represented by formula (1), wherein X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond;
An amide compound represented by formula (1), wherein X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH ₂ group;
An amide compound represented by formula (1), wherein X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH (CH ₃ ) group;
In the formula (1), X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is substituted with at least one group selected from the group [a-1]. An amide compound which may be a C3-C6 cycloalkyl group;
In Formula (1), X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is at least one selected from the group consisting of a halogen atom, a C1-C4 alkyl group and a hydroxyl group. An amide compound which is a C3-C6 cycloalkyl group optionally substituted with a species group;
In the formula (1), X ² is an amino group, and E ¹ is a 2-methylcyclopentyl group, 2-fluorocyclopentyl group, 2-chlorocyclopentyl group, 2-hydroxycyclopentyl group, 2-methylcyclohexyl group, 2-fluoro An amide compound which is a cyclohexyl group, a 2-chlorocyclohexyl group or a 2-hydroxycyclohexyl group;
In formula (1), X ² is an amino group, E ¹ is a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a (1-hydroxycyclobutyl) methyl group, a (1-hydroxycyclopentyl) methyl group, ( 1-hydroxycyclohexyl) methyl group, 1-cyclobutylethyl group, 1-cyclopentylethyl group, 1-cyclohexylethyl group, 1- (1-hydroxycyclobutyl) ethyl group, 1- (1-hydroxycyclopentyl) ethyl group or An amide compound which is a 1- (1-hydroxycyclohexyl) ethyl group;
An amide compound in which X ² is an amino group and E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ in formula (1);
In the formula (1), X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or C (CH ₃ ) Amide compound which is _two groups;
An amide compound represented by formula (1), wherein X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group;
An amide compound in which X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH (CH ₃ ) group in formula (1);
In formula (1), an amide compound in which X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ⁸ is a methyl group, and R ⁹ is a methyl group ;
In the formula (1), X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group, a CH (CH ₃ ) group or C (CH ₃ ) an amide compound having _two groups, R ⁸ is a methyl group, and R ⁹ is a methyl group;
In Formula (1), X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, R ⁸ is a methyl group, An amide compound in which R ⁹ is a methyl group;
In the formula (1), X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, and R ⁸ is a methyl group. An amide compound wherein R ⁹ is a methyl group;
In the formula (1), X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, and R ⁸ is methyl. An amide compound wherein R ⁹ is a methyl group;
In the formula (1), X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, a hydroxyl group An amide compound;
In the formula (1), an X ² is an amino group, a group E ¹ is represented by ^{A 2 -CR 8 R 9 R 10} , A 2 is CH ₂ group, R ¹⁰ is a hydrogen atom, C1- An amide compound which is a C4 alkyl group, a halogen atom, or a hydroxyl group;
In Formula (1), X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH (CH ₃ ) group, and R ¹⁰ is a hydrogen atom. An amide compound which is a C1-C4 alkyl group, a halogen atom or a hydroxyl group;
In Formula (1), X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a C (CH ₃ ) ₂ group, and R ¹⁰ is hydrogen. An amide compound which is an atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In the formula (1), X ² is an amino group, and E ¹ is a 2-methylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1,2,2-trimethylpropyl group, 2 An amide compound which is a methyl-2-hydroxypropyl group or a 1,2-dimethyl-2-hydroxypropyl group;

An amide compound in which in formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, and E ¹ is a group represented by A ¹ -Cy ¹ ;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , A ¹ is a single bond, CH ₂ group or An amide compound which is a CH (CH ₃ ) group;
An amide compound in which, in formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond;
In formula (1), an amide compound in which X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH ₂ group. ;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH (CH ₃ ) group. An amide compound;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is from group [a-1]. An amide compound which is a C3-C6 cycloalkyl group optionally substituted with at least one selected group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ¹ -Cy ¹ , Cy ¹ is a halogen atom, C1-C4 alkyl An amide compound which is a C3-C6 cycloalkyl group optionally substituted with at least one group selected from the group consisting of a group and a hydroxyl group;
In the formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a 2-methylcyclopentyl group, 2-fluorocyclopentyl group, 2-chlorocyclopentyl group, 2-hydroxycyclopentyl. An amide compound which is a group, 2-methylcyclohexyl group, 2-fluorocyclohexyl group, 2-chlorocyclohexyl group or 2-hydroxycyclohexyl group;
In the formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, or a (1-hydroxycyclobutyl) methyl group. , (1-hydroxycyclopentyl) methyl group, (1-hydroxycyclohexyl) methyl group, 1-cyclobutylethyl group, 1-cyclopentylethyl group, 1-cyclohexylethyl group, 1- (1-hydroxycyclobutyl) ethyl group, An amide compound which is a 1- (1-hydroxycyclopentyl) ethyl group or a 1- (1-hydroxycyclohexyl) ethyl group;

An amide compound represented by formula (1), wherein X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, and E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ ;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group. An amide compound which is a CH (CH ₃ ) group or a C (CH ₃ ) ₂ group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group. An amide compound;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is CH (CH ₃ ) an amide compound as a group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and R ⁸ is a methyl group. An amide compound wherein R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group. An amide compound having a CH (CH ₃ ) group or a C (CH ₃ ) ₂ group, R ⁸ is a methyl group, and R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group. An amide compound wherein R ⁸ is a methyl group and R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is CH (CH ₃ ) an amide compound wherein R ⁸ is a methyl group and R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is C (CH ₃ ) an amide compound having _two groups, R ⁸ is a methyl group, and R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ¹⁰ is a hydrogen atom, An amide compound which is a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group. An amide compound in which R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is CH (CH ₃ ) an amide compound in which R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is C (CH ₃ ) Amide compound which is ₂ groups and R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, a hydroxyl group;
In the formula (1), X ¹ is a fluorine atom, X ² is a 2-propynyloxy group, E ¹ is a 2-methylpropyl group, a 1,2-dimethylpropyl group, a 2,2-dimethylpropyl group, An amide compound which is a 1,2,2-trimethylpropyl group, a 2-methyl-2-hydroxypropyl group or a 1,2-dimethyl-2-hydroxypropyl group;
An amide compound in which X ¹ is a fluorine atom, X ² is an amino group, and E ¹ is a group represented by A ¹ -Cy ¹ in formula (1);
In the formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond, a CH ₂ group or CH (CH ₃ ) an amide compound as a group;
An amide compound in which, in formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a single bond;
An amide compound represented by formula (1), wherein X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH ₂ group;
In formula (1), an amide compound wherein X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and A ¹ is a CH (CH ₃ ) group ;

In Formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , and Cy ¹ is at least selected from the group [a-1]. An amide compound which is a C3-C6 cycloalkyl group optionally substituted by one group;
In the formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ¹ -Cy ¹ , Cy ¹ is a halogen atom, a C1-C4 alkyl group and a hydroxyl group An amide compound which is a C3-C6 cycloalkyl group optionally substituted with at least one group selected from the group consisting of groups;
In formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a 2-methylcyclopentyl group, a 2-fluorocyclopentyl group, a 2-chlorocyclopentyl group, a 2-hydroxycyclopentyl group, 2 An amide compound which is a methylcyclohexyl group, a 2-fluorocyclohexyl group, a 2-chlorocyclohexyl group or a 2-hydroxycyclohexyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a (1-hydroxycyclobutyl) methyl group, (1 -Hydroxycyclopentyl) methyl group, (1-hydroxycyclohexyl) methyl group, 1-cyclobutylethyl group, 1-cyclopentylethyl group, 1-cyclohexylethyl group, 1- (1-hydroxycyclobutyl) ethyl group, 1- ( An amide compound which is a 1-hydroxycyclopentyl) ethyl group or a 1- (1-hydroxycyclohexyl) ethyl group;
An amide compound in which X ¹ is a fluorine atom, X ² is an amino group, and E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ in formula (1);
In Formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, CH ( CH ₃₎ amide compound is a group or a C (CH _{3) 2} groups;
In formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH ₂ group. Compound;
In the formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A 2 is a CH (CH ₃ ) group. An amide compound;
In the formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ⁸ is a methyl group, R ^An amide compound wherein ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, CH ( An amide compound which is a CH ₃ ) group or a C (CH ₃ ) ₂ group, R ⁸ is a methyl group, and R ⁹ is a methyl group;
In the formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, An amide compound in which R ⁸ is a methyl group and R ⁹ is a methyl group;
In formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH (CH ₃ ) group. An amide compound wherein R ⁸ is a methyl group and R ⁹ is a methyl group;
In the formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is C (CH ₃ ) _2. An amide compound wherein R ⁸ is a methyl group and R ⁹ is a methyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , R ¹⁰ is a hydrogen atom, C1-C4 An amide compound which is an alkyl group, a halogen atom or a hydroxyl group;
In the formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , A ² is a CH ₂ group, An amide compound in which R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is a CH (CH ₃ ) group. An amide compound in which R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In the formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a group represented by A ² —CR ⁸ R ⁹ R ¹⁰ , and A ² is C (CH ₃ ) _2. An amide compound in which R ¹⁰ is a hydrogen atom, a C1-C4 alkyl group, a halogen atom, or a hydroxyl group;
In Formula (1), X ¹ is a fluorine atom, X ² is an amino group, E ¹ is a 2-methylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1,2 An amide compound which is a 2-methylpropyl group, a 2-methyl-2-hydroxypropyl group, or a 1,2-dimethyl-2-hydroxypropyl group;

  In the present specification, the structural formula of a compound may represent a certain isomer for convenience, but in the present invention, all active geometric isomers, optical isomers, stereoisomers, It includes isomers such as mutants and isomer mixtures, and is not limited to the description of the formula for convenience, and may be either one isomer or a mixture. Accordingly, there may be an optically active substance and a racemate having an asymmetric carbon atom in the molecule. However, the present invention is not particularly limited and includes any case.

  The compound of the present invention can be produced, for example, by the following (Production Method 1) to (Production Method 6).

〔式中、Ｅ¹、Ｘ¹及びＸ²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（以下、ＭＴＢＥと記す場合がある。）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（以下、ＤＭＳＯと記す場合がある）等のスルホキシド類及びこれらの混合物が挙げられる。
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。）及び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挙げられる。
化合物（２）１モルに対して、化合物（３）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、濾液を有機溶媒で抽出し、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、化合物（４）を単離することができる。単離された化合物（４）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)
Among the compounds of the present invention, the compound (4) in which Z ¹ is an oxygen atom can be produced by reacting the compound (2) and the compound (3) in the presence of a dehydration condensing agent.

[Wherein, E ¹ , X ¹ and X 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 tetrahydrofuran (hereinafter sometimes referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether (hereinafter sometimes referred to as MTBE), hexane, and the like. Aliphatic hydrocarbons such as pentane 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 -Acid amides such as dimethylformamide (hereinafter sometimes referred to as DMF), sulfoxides such as dimethylsulfoxide (hereinafter sometimes referred to as DMSO), and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC) and carbodiimides such as 1,3-dicyclohexylcarbodiimide.
The compound (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 (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 (4) 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 (4) can be further purified by chromatography, recrystallization and the like.

〔式中、Ｅ¹、Ｘ¹及びＸ²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ＴＨＦ、エチレングリコールジメチルエーテル、ＭＴＢＥ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、ＤＭＦ等の酸アミド類、ＤＭＳＯ等のスルホキシド類及びこれらの混合物が挙げられる。
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挙げられる。
化合物（２）１モルに対して、化合物（５）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で抽出し、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、化合物（４）を単離することができる。単離された化合物（４）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)
Among the compounds of the present invention, the compound (4) in which Z ¹ is an oxygen atom can be produced by reacting the compound (2) with the compound (5) or a hydrochloride thereof in the presence of a base.

[Wherein, E ¹ , X ¹ and X 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 THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogens such as chlorobenzene. Hydrocarbons, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as DMF, sulfoxides such as DMSO, 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 (5) 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 (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 (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 (4) can be further purified by chromatography, recrystallization and the like.

〔式中、Ｅ¹、Ｘ¹及びＸ²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ＴＨＦ、エチレングリコールジメチルエーテル、ＭＴＢＥ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、アセトニトリル、ブチロニトリル等の有機ニトリル類、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挙げられる。
化合物（４）１モルに対して、ローソン試薬が通常１〜２モルの割合で用いられる。
該反応の反応温度は通常２５〜１５０℃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で抽出し、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、化合物（６）を単離することができる。単離された化合物（６）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)
Among the compounds of the present invention, the compound (6) wherein Z ¹ is a sulfur atom is the compound (4) of the compounds of the present invention wherein Z ¹ is an oxygen atom and 2,4-bis (4-methoxyphenyl) -1,3. -It can be produced by reacting with dithia-2,4-diphosphetane-2,4-disulfide (hereinafter referred to as Lawson reagent).

[Wherein, E ¹ , X ¹ and X 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 THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogens such as chlorobenzene. Hydrocarbons, organic nitriles such as acetonitrile and butyronitrile, sulfoxides such as dimethyl sulfoxide, and mixtures thereof.
The Lawesson's reagent is usually used at a ratio of 1 to 2 moles relative to 1 mole of the compound (4).
The reaction temperature of the reaction is usually in the range of 25 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 (6) 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 (6) can be further purified by chromatography, recrystallization and the like.

〔式中、Ｅ¹、Ｘ¹及びＸ²は前記と同じ意味を表し、Ｌ¹はフッ素原子、塩素原子又は臭素原子を表す。〕
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ＴＨＦ、エチレングリコールジメチルエーテル、ＭＴＢＥ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、アセトン、イソブチルメチルケトン等のケトン類、アセトニトリル等のニトリル類、ＤＭＦ等の酸アミド類、ＤＭＳＯ等のスルホキシド類、水及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、水素化ナトリウム等のアルカリ金属水素化物、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級アミン類及びカリウム１，１−ジメチルエトキシド等のアルカリ金属アルコキシド類等が挙げられる。
化合物（７）１モルに対して、化合物（８）が通常１モル〜過剰量の割合、塩基が通常１〜１０モルの割合で用いられる。
反応終了後は、反応混合物を有機溶剤で抽出し、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、化合物（４）を単離することができる。単離された化合物（４）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)
Among the compounds of the present invention, the compound (4) in which Z ¹ is an oxygen atom can be produced by reacting the compound (7) and the compound (8) in the presence of a base.

[Wherein, E ¹ , X ¹ and X ² represent the same meaning as described above, and L ¹ represents a fluorine atom, a chlorine atom or a bromine atom. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogens such as chlorobenzene. Hydrocarbons, ketones such as acetone and isobutyl methyl ketone, nitriles such as acetonitrile, acid amides such as DMF, sulfoxides such as DMSO, water, and mixtures thereof.
Bases used for the reaction include alkali metal hydrides such as sodium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and potassium 1,1-dimethylethoxide. And alkali metal alkoxides.
The compound (8) is usually used in a proportion of 1 mol to excess and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the compound (7).
After completion of the reaction, the compound (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 (4) can be further purified by chromatography, recrystallization and the like.

〔式中、Ｅ¹、Ｘ¹及びＬ¹は前記と同じ意味を表し、Ｌ²は塩素原子、臭素原子、ヨウ素原子又はメタンスルホニルオキシ基を表し、Ｘ^2-1はメチル基又は２−プロピニル基を表し、Ｐｈはフェニル基を表す。〕
工程（Ｖ−１）
製造法４記載の方法に準じて、化合物（１０）は、化合物（７）とベンジルアルコールとを、塩基の存在下に反応させることにより製造することができる。
工程（Ｖ−２）
化合物（１１）は、化合物（１０）をパラジウム炭素存在下、水素と反応させることにより製造することができる。
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、メタノール、エタノール等のアルコール類、酢酸エチル等のエステル類、ＴＨＦ、ＭＴＢＥ等のエーテル類、水及びこれらの混合物が挙げられる。
化合物（１０）１モルに対して、パラジウム炭素が０．０１〜０．１モルの割合、水素が通常１〜２モルの割合で用いられる。
該反応の反応温度は通常０〜５０℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
該反応で使用する水素の圧力は、常圧〜１０気圧の範囲である。
反応終了後は、反応混合物を濾過し、濃縮する等の後処理操作を行うことにより、化合物（１１）を単離することができる。単離された化合物（１１）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。
また、化合物（１１）は、化合物（７）と水酸化ナトリウム等のアルカリ金属水酸化物とを反応させることにより、化合物（１０）を経由することなく製造することもできる。
工程（Ｖ−３）
化合物（１３）は、化合物（１１）と化合物（１２）とを、塩基の存在下で反応させることにより製造することができる。
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、トルエン、ヘキサン等の炭化水素類、アセトン、メチルイソブチルケトン等のケトン類、ＤＭＦ等の酸アミド類及びＤＭＳＯ等のスルホキシド類が挙げられる。
反応に用いられる塩基としては、例えば炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩類、水素化ナトリウム等のアルカリ金属水素化物等が挙げられる。
化合物（１１）１モルに対して、化合物（１２）が通常１〜３モルの割合、塩基が通常１〜３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０．５〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、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、化合物（１３）を単離することができる。単離された化合物（１３）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 5)
Among the compounds of the present invention, the compound represented by the formula (13) can be produced by the method shown in the following scheme.

[Wherein E ¹ , X ¹ and L ¹ represent the same meaning as described above, L ² represents a chlorine atom, a bromine atom, an iodine atom or a methanesulfonyloxy group, and X ^2-1 represents a methyl group or 2-propynyl. Represents a group, and Ph represents a phenyl group. ]
Step (V-1)
In accordance with the method described in Production Method 4, compound (10) can be produced by reacting compound (7) with benzyl alcohol in the presence of a base.
Process (V-2)
Compound (11) can be produced by reacting compound (10) with hydrogen in the presence of palladium on carbon.
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, alcohols such as methanol and ethanol, esters such as ethyl acetate, THF, and the like. , Ethers such as MTBE, water, and mixtures thereof.
Palladium carbon is used in a proportion of 0.01 to 0.1 mol and hydrogen is usually used in a proportion of 1 to 2 mol with respect to 1 mol of compound (10).
The reaction temperature of the reaction is usually in the range of 0 to 50 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
The pressure of hydrogen used in the reaction is in the range of normal pressure to 10 atm.
After completion of the reaction, the compound (11) can be isolated by performing post-treatment operations such as filtration and concentration of the reaction mixture. The isolated compound (11) can be further purified by chromatography, recrystallization and the like.
Moreover, a compound (11) can also be manufactured without going through a compound (10) by making a compound (7) and alkali metal hydroxides, such as sodium hydroxide, react.
Process (V-3)
Compound (13) can be produced by reacting compound (11) with compound (12) 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 hydrocarbons such as toluene and hexane, ketones such as acetone and methyl isobutyl ketone, acid amides such as DMF, and sulfoxides such as DMSO.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, and alkali metal hydrides such as sodium hydride.
The compound (12) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 3 mol with respect to 1 mol of the compound (11).
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 0.5 to 24 hours.
After completion of the reaction, the compound (13) 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 (13) can be further purified by chromatography, recrystallization and the like.

〔式中、Ｘ¹及びＸ²は前記と同じ意味を表し、Ｒ¹⁵はフッ素原子、塩素原子、臭素原子、ヨウ素原子、Ｃ１−Ｃ３アルキルチオ基又はＣ１−Ｃ６アルコキシ基を表す。〕
工程（VI−１）
製造法２記載の方法に準じて、化合物（１４）は、化合物（５）と７−アザビシクロ[４．１．０]ヘプタンとを、塩基の存在下に反応させることにより製造することができる。
工程（VI−２）
化合物（１５）は、化合物（１４）と下記に挙げられる試薬とを反応させることにより製造することができる。
該反応に用いられる試薬としては、化合物（１５）におけるＲ¹⁵がフッ素原子である場合には、フッ化カリウム、フッ化リチウム等のアルカリ金属フッ化物、フッ化カルシウム等のアルカリ土類金属フッ化物、テトラブチルアンモニウムフロリド等の４級アンモニウムフロリド類及びフッ化水素等のフッ素化剤が挙げられ、
化合物（１５）におけるＲ¹⁵が塩素原子である場合には、塩化ナトリウム、塩化リチウム等のアルカリ金属塩化物、塩化マグネシウム等のアルカリ土類金属塩化物、塩化アルミニウム、塩化亜鉛（ＩＩ）等の金属塩化物、テトラブチルアンモニウムクロリド等の４級アンモニウムクロリド、トリメチルシリルクロリド等の有機ケイ素塩化物、塩化チオニル等の硫黄化合物、オキシ塩化リン、三塩化リン、五塩化リン等のリン化合物及び塩化水素等の塩素化剤が挙げられ、
化合物（１５）におけるＲ¹⁵が臭素原子である場合には、臭化ナトリウム等のアルカリ金属臭化物、臭化マグネシウム等のアルカリ土類金属臭化物、臭化亜鉛（ＩＩ）等の金属臭化物、テトラブチルアンモニウムブロミド等の４級アンモニウムブロミド、トリメチルシリルブロミド等の有機ケイ素臭化物、三臭化リン等のリン化合物及び臭化水素等の臭素化剤が挙げられ、
化合物（１５）におけるＲ¹⁵がヨウ素原子である場合には、ヨウ化カリウム等のアルカリ金属ヨウ化物、ヨウ化マグネシウム等のアルカリ土類金属ヨウ化物、ヨウ化亜鉛（ＩＩ）等の金属ヨウ化物、テトラブチルアンモニウムヨージド等の４級アンモニウムヨージド、トリメチルシリルヨージド等の有機ケイ素化合物及びヨウ化水素等のヨウ素化剤が挙げられ、
化合物（１５）におけるＲ¹⁵がＣ１−Ｃ３アルキルチオ基である場合には、Ｃ１−Ｃ３アルキルメルカプタンが挙げられ、
化合物（１５）におけるＲ¹⁵がＣ１−Ｃ６アルコキシ基である場合には、Ｃ１−Ｃ６アルコールが挙げられる。
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ＴＨＦ、エチレングリコールジメチルエーテル、ＭＴＢＥ等のエーテル類、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、クロロホルム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、ＤＭＦ等の酸アミド類、水及びこれらの混合物が挙げられる。
化合物（１４）１モルに対して、上記の試薬が通常１〜５モルの割合で用いられる。
該反応の反応温度は通常−２０〜１５０℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
該反応は、必要に応じて添加剤の存在下で行うこともできる。かかる添加剤としては、例えばトリブチルフォスフィン等のリン化合物が挙げられる。
上記記載のＣ１−Ｃ３アルキルメルカプタン及びＣ１−Ｃ６アルコールは、水素化ナトリウム等のアルカリ金属水素化物等と反応させることによりアルカリ金属塩に調製した後、該反応に用いることもできる。
反応終了後は、反応混合物を有機溶媒で抽出し、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、化合物（１５）を単離することができる。単離された化合物（１５）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。
化合物（１５）のうち、Ｒ¹⁵が塩素原子であるアミド化合物は、化合物（４）と７−アザビシクロ[４．１．０]ヘプタンとを反応させた後、そのまま、前記の塩素化剤と反応することにより合成することもできる。 (Production method 6)
Among the compounds of the present invention, the compound represented by the formula (15) can be produced by the method shown in the following scheme.

[Wherein, X ¹ and X ² represent the same meaning as described above, and R ¹⁵ represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C1-C3 alkylthio group or a C1-C6 alkoxy group. ]
Process (VI-1)
In accordance with the method described in Production Method 2, compound (14) can be produced by reacting compound (5) with 7-azabicyclo [4.1.0] heptane in the presence of a base.
Process (VI-2)
Compound (15) can be produced by reacting compound (14) with the reagents listed below.
As a reagent used in the reaction, when R ¹⁵ in the compound (15) is a fluorine atom, an alkali metal fluoride such as potassium fluoride or lithium fluoride, or an alkaline earth metal fluoride such as calcium fluoride Quaternary ammonium fluorides such as tetrabutylammonium fluoride and fluorinating agents such as hydrogen fluoride,
When R ¹⁵ in the compound (15) is a chlorine atom, an alkali metal chloride such as sodium chloride or lithium chloride, an alkaline earth metal chloride such as magnesium chloride, a metal such as aluminum chloride or zinc chloride (II) Chlorides, quaternary ammonium chlorides such as tetrabutylammonium chloride, organosilicon chlorides such as trimethylsilyl chloride, sulfur compounds such as thionyl chloride, phosphorus compounds such as phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, and hydrogen chloride Chlorinating agents,
When R ¹⁵ in the compound (15) is a bromine atom, an alkali metal bromide such as sodium bromide, an alkaline earth metal bromide such as magnesium bromide, a metal bromide such as zinc (II) bromide, tetrabutylammonium Examples include quaternary ammonium bromides such as bromide, organosilicon bromides such as trimethylsilyl bromide, phosphorus compounds such as phosphorus tribromide and brominating agents such as hydrogen bromide.
When R ¹⁵ in the compound (15) is an iodine atom, an alkali metal iodide such as potassium iodide, an alkaline earth metal iodide such as magnesium iodide, a metal iodide such as zinc (II) iodide, Quaternary ammonium iodides such as tetrabutylammonium iodide, organosilicon compounds such as trimethylsilyl iodide and iodinating agents such as hydrogen iodide,
In the case where R ¹⁵ in the compound (15) is a C1-C3 alkylthio group, a C1-C3 alkyl mercaptan may be mentioned,
When R ¹⁵ in the compound (15) is a C1-C6 alkoxy group, a C1-C6 alcohol is exemplified.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene and chloroform, butyl acetate, and ethyl acetate. Examples thereof include esters, nitriles such as acetonitrile, acid amides such as DMF, water, and mixtures thereof.
The above-mentioned reagent is usually used at a ratio of 1 to 5 moles relative to 1 mole of the compound (14).
The reaction temperature of the reaction 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.
This reaction can also be performed in presence of an additive as needed. Examples of such additives include phosphorus compounds such as tributylphosphine.
The C1-C3 alkyl mercaptan and C1-C6 alcohol described above can also be used in the reaction after preparing an alkali metal salt by reacting with an alkali metal hydride such as sodium hydride.
After completion of the reaction, the compound (15) 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 (15) can be further purified by chromatography, recrystallization and the like.
Among the compounds (15), an amide compound in which R ¹⁵ is a chlorine atom reacts with the chlorinating agent as it is after reacting the compound (4) with 7-azabicyclo [4.1.0] heptane. Can also be synthesized.

〔式中、Ｘ¹及びＸ²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、アセトニトリル等のニトリル類、クロロベンゼン等のハロゲン化炭化水素類、ＤＭＦ等の酸アミド類及びこれらの混合物が挙げられる。
化合物（３）１モルに対して、塩化チオニルが通常１〜５モルの割合で用いられる。
該反応の反応温度は通常２０〜１５０℃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、反応混合物を濃縮する等の後処理操作を行うことにより、化合物（５）を単離することができる。単離された化合物（５）は、再結晶等によりさらに精製することもできる。 Some of the intermediate compounds used for the synthesis of the compound of the present invention are commercially available or disclosed in known literature. Moreover, an intermediate compound can be manufactured by the following method, for example.
(Intermediate production method 1)
Compound (5) or a hydrochloride thereof can be produced by reacting compound (3) with thionyl chloride.

[Wherein, X ¹ and X 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 aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, nitriles such as acetonitrile, halogenated hydrocarbons such as chlorobenzene, DMF, and the like. And acid amides and mixtures thereof.
Thionyl chloride is usually used at a ratio of 1 to 5 moles relative to 1 mole of the compound (3).
The reaction temperature of the reaction 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 (5) can be isolated by post-treatment such as concentration of the reaction mixture. The isolated compound (5) can be further purified by recrystallization or the like.

  The control agent of the present invention is usually prepared by mixing the compound of the present invention with a liquid carrier, solid carrier, gas carrier, surfactant, etc., and if necessary, adding an auxiliary for formulation such as a binder and a thickener. It is formulated into a powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule and the like. In these preparations, the compound of the present invention is usually contained in an amount of 0.1 to 99%, preferably 0.2 to 90% by weight.

  Examples of the liquid carrier used for formulation include water, alcohols (eg, methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, etc.), ketones (eg, acetone, methyl ethyl ketone, etc.), Ethers (eg, dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether), aliphatic hydrocarbons (eg, hexane, octane, cyclohexane, kerosene, fuel oil, machine oil, etc.), aroma Group hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides (eg, Methylformamide, dimethylacetamide, N- methylpyrrolidone), esters (e.g., ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), nitriles (e.g., acetonitrile, and propionitrile, etc.) and the like. Two or more of these liquid carriers can be mixed and used in an appropriate ratio.

  Solid carriers used for formulation include vegetable powders (for example, soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powders (for example, kaolin, bentonite, acid clay, clays such as clay) Talc such as talc powder and wax stone powder, silica such as diatomaceous earth and mica powder), alumina, sulfur powder, activated carbon, saccharides (eg lactose, glucose etc.), inorganic salts (eg calcium carbonate, sodium bicarbonate) Etc.), glass hollow bodies (natural glassy materials fired and encapsulated with bubbles), and the like. Two or more kinds of these solid carriers can be mixed and used at an appropriate ratio. The liquid carrier or solid carrier is usually used in an amount of 1 to 99% by weight, preferably about 10 to 99% by weight, based on the whole preparation.

  A surfactant is usually used as an emulsifier, a dispersant, a spreading agent, a penetrating agent, a wetting agent and the like used for formulation. Surfactants include, for example, anions such as alkyl sulfate esters, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates, etc. Nonionic surfactants such as surfactants and polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters and the like can be mentioned. Two or more of these surfactants can be used. The surfactant is usually used in a proportion of 0.1 to 50% by weight, preferably about 0.1 to 25% by weight, based on the whole preparation.

  Examples of the binder or thickener include dextrin, sodium salt of carboxymethyl cellulose, polycarboxylic acid polymer compound, polyvinyl pyrrolidone, polyvinyl alcohol, sodium lignin sulfonate, calcium lignin sulfonate, sodium polyacrylate, gum arabic Sodium alginate, mannitol, sorbitol, bentonite minerals, polyacrylic acid and its derivatives, sodium salt of carboxymethyl cellulose, white carbon, natural sugar derivatives (for example, xanthan gum, guar gum, etc.), and the like.

  In addition, the present control agent may be used simultaneously with or without mixing with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers or soil conditioners. You can also.

  Such other fungicides include, for example, propiconazole, prothioconazole, triazimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumi Azole fungicides such as sol, tetraconazole, microbutanyl, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, viteltanol, imazalil, flutriahol, cimeconazole, ipconazole; fenpropimorph, tridemorph, Cyclic amine fungicides such as phenpropidin; benzimidazole fungicides such as carbendazim, benomyl, thiabendazole and thiophanate methyl Cyprodinil; Pyrimethanil; Diethofencarb; Thiuram; Fluazinam; Mancozeb; Iprodione; Vinclozoline; Chlorotalonyl; Captan; Mepanipyrim; Oxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; metminostrobin; enestrobine; spiroxamine; quinoxifen; fenhexamide; famoxadone; fenamidone; zoxamide; ethaboxam; amisulbrom; Avaricarb; Ciazofamide; Mandipropamide; Boscalid; Penthiopyrad Metrafenone; fluopyran; bixafen; cyflufenamide; proquinazide; orizastrobin; furametopyr; tifluzamide; mepronil; flutolanil; flusulfamide; Provenazole; Isothianyl; Thiazinyl; Tebufloquine; Diclomedin; Kasugamycin; Ferimzone; Fusaride; Validamycin; Hydroxyisoxazole; Iminoctazine acetate; Isoprothiolane; Oxolinic acid; Oxytetracycline; Streptomycin; Copper sulfate, organic copper, sulfur, etc. Can be mentioned.

Examples of such other insecticides include (1) organophosphorus compounds such as acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyphos, chlorfenbinphos. (Ch1orfenvinphos), chlorpyrifos (chlorpyrifos-methyl), cyanophos (CYAP), diazinon (diazoention), chlorpyrifos dithione rvos: DDVP), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprofos, etrimfos, fenthion, phenthion MP MEP), fothiazate, formothione, hydrogen phosphide, isofenphos, isoxathion, malathion, methulfenfos (mesulfenthios) Dathion: DMTP), Monocrotophos, Nared: BRP, Oxydeprofos: ESP, Parathion, Phosalone, Phosmet: PMP, Pirimiphosmethyl-1 , Pyridafenthion, quinalphos, phentoate (PAP), profenofos, propopafos, prothiofos (prothiofos), pyrachlorfosul os), tebupyrimfos (tebupirimfos), temephos (temephos), tetrachlorbinphos (tetrachphos), terbufos (terbufos), thiometon (trimethorphon: DEP), bamidthione (v) cadusafos) and the like;

(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, BPMC, carbaryl (carbary), carbofuran, carbothofen, carbotophene ), Fenobucarb, phenothiocarb, phenoxycarb, furathiocarb, isoprocarb (MIPC), metocarbyl, metolcarb thiocarb), NAC, oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), aldicarb (aldicarb) or the like;

(3) Synthetic pyrethroid compounds Acrinathrin, Allethrin, Benfluthrin, Beta-Cyfluthrin, Bifenthrin, Cycloprothrin, Cycloprothrin (Cycloprothrin) cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropratrin, fenvalerate, fenvalate (Flucythrinate), flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, praletrin. (Resmethrin), sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin (tetraflutrin), tetramethrin (etrmethrin) methrin), phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda cithalthrin (lambda-thalmethrin) (Tau-flavinate), 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1- Enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl -3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- ( 2-methyl-1-propenyl) cyclopropanecarboxylate and the like;

(4) Nereistoxin compounds Cartap, bensultap, thiocyclam, monosultap, bisultap, etc .;

(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamipride), thiamethoxam (thiacloprid) (thiacloprid), dinotefur (din)

(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxron, flucycloxuron Flufluxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuuron, triflumuuron, etc.

(7) Phenylpyrazole compounds Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, etc .;
(8) Bt toxin insecticide, live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, tebufenozide and the like;
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor and the like;
(11) Natural insecticide machine oil, nicotine sulfate (nicotine-sulfate);

(12) Other insecticides avermectin (avermectin-B), bromopropyrate, buprofezin, chlorphenapyr, cyromazine, benzo (p), benzo (p) emamectin-benzoate, phenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiamine etrozine, pyridalyl, pyriproxyfen, spinosad, sulfuramide, tolfenpyrad, triazemate i, flubenamide i, flubendiamide f Arsenic acid, Benclothiaz, lime nitrogen (Calcium polysulfide), chlordane, DDT, DSP, flufenemide, flufenerimide Flurimfen, formatenate, metham-ammonium, metham-sodium, methyl bromide, ninototefuran, potassium oleate, oleate Trifenbute, spiromesifen, sulfur, metaflumizone, spirotetramat, pyrifluquinone, pitraquinone, pitraquinone aniliprole)
And the like.

  Examples of such other acaricides (acaricidal active ingredients) include, for example, acequinocyl, amitraz, benzoximate, biphenate, phenisobromolate, quinomethionate, and quinomethionate. , Chlorbenzilate, CPCBS (chlorfenson), clofentezine, cyflumetofen, quercene (dicofol), ethoxazole, thiobutofin tin , Fenpyroximate, fluacrylpyrim, fluproxyfen, hextiazox, propargite, BP, and polynactin complex. ), Tetradiphon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cienopyrafen (cyeno) yrafen), and the like.

  Examples of such other nematicides (nematicidal active ingredients) include, for example, DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartarate, iciafos Etc.

The weight ratio of the active ingredient to the fungicide mixed or used in combination with the present control agent is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
The weight ratio of the active ingredient to the insecticide to be mixed or used in combination with the present control agent is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
The weight ratio of the active ingredient to the acaricide used together with or in combination with the control agent of the present invention is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
The weight ratio of the active ingredient to the nematicide used in combination with or in combination with the control agent of the present invention is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
The weight ratio of the active ingredient to the herbicide used in combination with or in combination with the control agent of the present invention is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
The weight ratio of the active ingredient to the plant growth regulator used in combination with or in combination with the control agent of the present invention is usually in the range of 1: 0.00001 to 1: 100, preferably 1: 0.0001 to 1: 1.
The ratio of the fertilizer or soil improver used in combination with or in combination with the control agent of the present invention is usually in the range of 1: 0.1 to 1: 1000, preferably 1: 1 to 1: 200.

  The method for applying the control agent of the present invention is not particularly limited as long as the compound of the present invention can be applied substantially. For example, treatment of useful plant crops such as spraying of foliage to plants, useful crops, etc. Examples include treatment of planted or planted soil such as planted soil, treatment of seeds such as seed disinfection, and the like.

  The application amount of the control agent of the present invention varies depending on weather conditions, formulation form, application time, application method, application place, target disease, target crop, etc., but per 10 are by weight of the present compound in the control agent of the present invention Usually, 1 to 500 g, preferably 2 to 200 g. Emulsions, wettable powders, suspensions and the like are usually diluted with water before use. In this case, the concentration of the compound of the present invention after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to It is 1% by weight, and powders, granules and the like are usually applied as they are without dilution. In the treatment for seeds, it is usually applied in the range of 0.001 to 100 g, preferably 0.01 to 50 g in terms of the weight of the compound of the present invention in the control agent of the present invention per 1 kg of seeds.

  The control agent of the present invention can be used as a control agent for plant diseases caused by phytopathogenic fungi in agricultural fields such as fields, paddy fields, lawns, orchards. The control agent of the present invention can control plant diseases caused by phytopathogenic fungi in the cultivated land in cultivated lands where the following “crop” and the like are cultivated.

Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplant, tomato, pepper, pepper, potato) Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae (burdock, Shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, red pepper, etc.), red crustacean vegetables (spinach, chard, etc.) (Perilla, mint, basil ), Strawberry, sweet potato, yam, taro, etc.,
Flower buds;
Foliage plant;
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.

  The above “crop” has resistance to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, herbicides such as bromoxynil, This includes crops granted by classical breeding methods or genetic engineering techniques.

  As an example of “crop” to which resistance is imparted by a classic breeding method, imidazolinone herbicide-resistant Clearfield (registered trademark) canola, such as imazetapil, and sulfonylurea-type ALS-inhibiting herbicide-resistant herbicides such as thifensulfuron methyl There are STS soybeans. Examples of “crop” to which tolerance has been imparted by genetic recombination technology include glyphosate and glufosinate-resistant corn varieties, which are already sold under trade names such as RoundupReady (registered trademark) and LibertyLink (registered trademark). Has been.

The “crop” includes, for example, a crop that can synthesize selective toxins known in the genus Bacillus by using genetic recombination technology.
Examples of toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popirie; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 and Cry9C derived from Bacillus thuringiensis Insecticidal proteins such as δ-endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plants Lectin; agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc. Ribosome inactivating protein (RIP); steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-COA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitors; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase;

In addition, as toxins expressed in such genetically modified crops, hybrids of insecticidal proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, and the like, δ-endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A Toxins, partially defective toxins, modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073, and the like.
The toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.

  Also, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known and some are commercially available. Examples of these transgenic plants include YieldGard® (a corn variety that expresses Cry1Ab toxin), YieldGuard Rootworm® (a corn variety that expresses Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1) Corn varieties expressing toxin), Herculex I® (corn varieties expressing phosphinotricin N-astilyl transferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties that express), Bollgard I (registered trademark) (cotton varieties that express Cry1Ac toxin), Bollgard II (registered trademark) (Cry1Ac and cotton varieties expressing ry2Ab toxin), VIPCOT® (cotton varieties expressing VIP toxin), NewLeaf® (potato varieties expressing Cry3A toxin), NatureGard® Agriure® Examples include GT Advantage (GA21 glyphosate resistant trait), Agurisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), Protecta (registered trademark), and the like.

The above “crop” includes those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
PR proteins and the like are known as examples of anti-pathogenic substances (PRPs, EP-A-0 392 225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191 and the like.
Examples of anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.). Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; PR protein; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes, WO 03/000906)) and the like, and the like, and the like, which are produced by microorganisms.

  Examples of plant diseases that can be controlled by the present invention include plant diseases caused by phytopathogenic filamentous fungi, and more specifically, the following diseases can be mentioned, but are not limited thereto. .

  Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiotic seedling (Gibberella fujikuroi) or yellow rot Erysiphe graminis), Fusarium graminearum, F. avenacerum, F. culmorum, Microchiumium varieties, Rust (Puccinia striformis, P. graminis, P. graminis, P. graminis, P. Micronetriella niva is), Bare Scab (Ustilago tritici, U. nuda), Tuna Thornia caries, Pyodercosporella herpotrichoides, Cloudy disease (Rhynchosporiat disease) Leptopharia nodorum, Pyrenophora teres Drechsler, Blight (Gaeumanomyces graminis), Pyrenophora tritici-repentis; Black spot of citrus (Penicil Ium digitatum, P. italicum); Moniliaia mali, rot (Valsa ceratosperma), powdery mildew (Podosphaera leukotria), leaf spot (Alternaria paparia) The disease (Glomerella cingula); Pear black spot disease (Venturia nashicola, V. pirina); Black spot disease (Alternaria alternata Japan pathotype); Red star disease (Gymnosporum) uticola, black scab (Cladosporium carpophilum), phomopsis spoilage (Phomopsis sp.); grape black rot (Elsinoe ampelina), late rot (Glomerella cinulata), powdery mildew (Uncul) ), Blacklot's disease (Plasmopara viticola); Oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella charcoal); Disease (Sp aerotheca fuliginea), vine blight (Mycosphaerella melonis), Fusarium disease (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora sp. ), Seedling blight (Pythium sp.); Tomato ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans); eggplant brown rot (Phomopsis vexans) Erysiphe cichoracerum); Black spot disease of cruciferous vegetables (Alternaria japonica), white spot disease (Cercosporella brassicae), root-knot disease (Plasmodiophora brassicae), downy mildew (Peronosorposis) Purpura (Cercospora kikuchii), black scab (Elsi) oe glycines, black spot disease (Diaporthe phaseolum var. sojae), rust disease (Pharkopsora pachyrhizi), black anthracnose (Colletotrichum lindemthianum) Disease (Sclerotium rolfsiii); Pea powdery mildew (Erysiphe pisii); Potato summer infestation, Phytophthora infestans, Verticillium vulgaris. Powdery mildew (Sphaerotheca humuli); Chamodium wilt (Exobasidium reticulatum); White scab (Elsinoe leucospila); Ring spot disease (Pestalolithis sp.); longipes), powdery mildew (Erysiphe cichoacearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacuma), plague (Phytophthora nicotiana et al., leaf blight) ris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces sochlioides); rose scab (Diplocarpon rosae); powdery mildew (Sphaerotheca pannosa); (Puccinia horiana); onion white leaf blight (Botrytis cinerea, B. et al.). Byssoidea, B. squamosa), gray rot (Botrytis alli); Botrytis squamosa, various crops of gray rot (Botrytis cinerea), sclerotia sclerotia; Alternaria brassicicola); Sclerotinia homeocarpa, Brown patch disease and Rhizotonia solanii; and Banana's Mycosphaerellas filipinos.

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.

¹H-NMR (CDCl₃) δ: 2.52 (1H, t, J = 2.4 Hz), 2.54 (1H, t, J = 2.4 Hz), 4.93 (2H, d, J = 2.4 Hz), 5.13 (2H, d, J = 2.4 Hz), 7.95 (1H, dd, J = 10.0, 1.8 Hz), 8.66 (1H, d, J = 1.8 Hz).
５−フルオロ−６−（２−プロピニルオキシ）ニコチン酸（２−プロピニル）０．２０ｇ及び１５％水酸化ナトリウム水溶液１ｍｌをＴＨＦ４ｍｌに加え、２時間加熱還流した。室温付近まで放冷した反応混合物を１０％クエン酸水溶液に加え、酢酸エチルで３回抽出した。有機層を硫酸マグネシウムで乾燥し、減圧下濃縮して、５−フルオロ−６−（２−プロピニルオキシ）ニコチン酸を得た。
５−フルオロ−６−（２−プロピニルオキシ）ニコチン酸及び塩化チオニル０．２０ｇをトルエン５ｍｌに加えた後、ＤＭＦを１滴加えて、２時間加熱還流した。室温付近まで放冷した反応混合物を減圧下濃縮した。得られた残渣とシクロヘキシルメチルアミン０．２０ｇとをＴＨＦ５ｍｌに加えた後、トリエチルアミン０．２０ｇを滴下した。室温で１日間攪拌した。反応混合物を減圧下濃縮し、残渣をシリカゲルカラムクロマトグラフィーに付し、Ｎ−（シクロヘキシルメチル）−５−フルオロ−６−（２−プロピニルオキシ）ニコチン酸アミド（以下、本発明化合物１と記す。）７２ｍｇを得た。
本発明化合物１

¹H-NMR (CDCl₃) δ: 0.94-1.30 (5H, m), 1.52-1.84 (6H, m), 2.50-2.52 (1H, m), 3.30 (2H, t, J = 6.5 Hz), 5.10 (2H, d, J = 2.4 Hz), 6.10 (1H, br s), 7.82 (1H, dd, J = 10.2, 2.0 Hz), 8.32 (1H, d, J = 2.0 Hz). Production Example 1
2,6-dichloro-5-fluoronicotinic acid (5.0 g) and 15% sodium hydroxide (4.0 g) were added to water (40 ml), and the mixture was heated to reflux for 3 hours. The reaction mixture was allowed to cool to near room temperature and acidified by adding hydrochloric acid, and the resulting solid was collected by filtration and dried to give 2-chloro-5-fluoro-6-hydroxynicotinic acid.
2-Chloro-5-fluoro-6-hydroxynicotinic acid and 300% of 10% palladium carbon were added to 70 ml of methanol, and reacted for 5 hours in a hydrogen atmosphere. The reaction mixture was made alkaline with an aqueous sodium hydroxide solution, filtered through Celite (registered trademark), and concentrated under reduced pressure. Hydrochloric acid was added to the residue to make it acidic, and the resulting solid was collected by filtration and dried to obtain 3.0 g of 5-fluoro-6-hydroxynicotinic acid.
3.0 g of 5-fluoro-6-hydroxynicotinic acid, 2.7 g of propargyl alcohol and 12.5 g of triphenylphosphine were added to 30 ml of THF, and 22 ml of diethyltoluene azodicarboxylate solution (2.2 M) was added at room temperature. For 1 day. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to give 0.20 g of 5-fluoro-6- (2-propynyloxy) nicotinic acid (2-propynyl), 5-fluoro-6-oxo-1 3.6 g of-(2-propynyl) -1,6-dihydronicotinic acid (2-propynyl) was obtained.
5-Fluoro-6- (2-propynyloxy) nicotinic acid (2-propynyl)

¹ H-NMR (CDCl ₃ ) δ: 2.52 (1H, t, J = 2.4 Hz), 2.54 (1H, t, J = 2.4 Hz), 4.93 (2H, d, J = 2.4 Hz), 5.13 (2H, d, J = 2.4 Hz), 7.95 (1H, dd, J = 10.0, 1.8 Hz), 8.66 (1H, d, J = 1.8 Hz).
0.20 g of 5-fluoro-6- (2-propynyloxy) nicotinic acid (2-propynyl) and 1 ml of 15% aqueous sodium hydroxide solution were added to 4 ml of THF, and the mixture was heated to reflux for 2 hours. The reaction mixture was allowed to cool to near room temperature, added to a 10% aqueous citric acid solution, and extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 5-fluoro-6- (2-propynyloxy) nicotinic acid.
5-Fluoro-6- (2-propynyloxy) nicotinic acid and 0.20 g of thionyl chloride were added to 5 ml of toluene, 1 drop of DMF was added, and the mixture was heated to reflux for 2 hours. The reaction mixture allowed to cool to around room temperature was concentrated under reduced pressure. The obtained residue and 0.20 g of cyclohexylmethylamine were added to 5 ml of THF, and then 0.20 g of triethylamine was added dropwise. Stir at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography, and N- (cyclohexylmethyl) -5-fluoro-6- (2-propynyloxy) nicotinamide (hereinafter referred to as the present compound 1). ) 72 mg was obtained.
Compound 1 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 0.94-1.30 (5H, m), 1.52-1.84 (6H, m), 2.50-2.52 (1H, m), 3.30 (2H, t, J = 6.5 Hz), 5.10 (2H, d, J = 2.4 Hz), 6.10 (1H, br s), 7.82 (1H, dd, J = 10.2, 2.0 Hz), 8.32 (1H, d, J = 2.0 Hz).

¹H-NMR (CDCl₃) δ: 8.11 (1H, dd, J = 7.9, 1.8 Hz), 8.92 (1H, d, J = 1.8 Hz).
６−クロロ−５−フルオロニコチン酸１．５ｇ、２−メチルシクロヘキシルアミン１．１ｇ、１−ヒドロキシベンゾトリアゾール１．５ｇ及びＷＳＣ２．１ｇをＤＭＦ１５ｍｌに加え、１３０℃で１０分間、次いで室温で１日間攪拌した。反応混合物に飽和炭酸水素ナトリウム水溶液を加え、酢酸エチルで抽出した。有機層を水及び飽和食塩水で順次洗浄後、硫酸マグネシウムで乾燥し、減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、Ｎ−（２−メチルシクロヘキシル）−６−クロロ−５−フルオロニコチン酸アミド１．６ｇを得た。
Ｎ−（２−メチルシクロヘキシル）−６−クロロ−５−フルオロニコチン酸アミド

¹H-NMR (CDCl₃) δ: 0.94 (0.9H, d, J = 6.8 Hz), 0.98 (2.1H, d, J = 6.3 Hz), 1.10-1.84 (8.0H, m), 1.97-2.08 (1.0H, m), 3.66-3.76 (0.7H, m), 4.24-4.30 (0.3H, m), 5.81-5.89 (0.7H, br m), 6.04-6.10 (0.3H, br m), 7.90-7.94 (1.0H, m), 8.51-8.53 (1.0H, m).
Ｎ−（２−メチルシクロヘキシル）−６−クロロ−５−フルオロニコチン酸アミド０．４０ｇ、プロパルギルアルコール０．２５ｇ及び水素化ナトリウム７１ｍｇをＤＭＦ１０ｍｌに加え、室温で８時間攪拌した。反応混合物にクエン酸水溶液を加え、酢酸エチルで抽出した。有機層を水及び飽和食塩水で順次洗浄し、硫酸マグネシウムで乾燥した後、減圧下濃縮した。残渣をシリカゲルカラムクロマトグラフィーに付し、Ｎ−（２−メチルシクロヘキシル）−５−フルオロ−６−（２−プロピニルオキシ）ニコチン酸アミド（以下、本発明化合物２と記す。）０．２７ｇを得た。
本発明化合物２

¹H-NMR (CDCl₃) δ: 0.93 (0.9H, d, J = 7.1 Hz), 0.98 (2.1H, d, J = 6.3 Hz), 1.09-1.82 (8.0H, m), 1.92-2.08 (1.0H, m), 2.50-2.52 (1.0H, m), 3.64-3.73 (0.7H, m), 4.22-4.28 (0.3H, m), 5.09-5.10 (2.0H, m), 5.75-5.81 (0.7H, br m), 6.00-6.05 (0.3H, br m), 7.80-7.84 (1.0H, m), 8.31 (0.7H, d, J = 2.0 Hz), 8.32 (0.3H, d, J = 2.0 Hz). Production Example 2
2.9 g of 5-fluoro-6-hydroxynicotinic acid was added to 20 ml of phosphorus oxychloride and heated to reflux for 2 hours. The reaction mixture allowed to cool to near room temperature was added to water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to obtain 1.7 g of 6-chloro-5-fluoronicotinic acid.
6-chloro-5-fluoronicotinic acid

¹ H-NMR (CDCl ₃ ) δ: 8.11 (1H, dd, J = 7.9, 1.8 Hz), 8.92 (1H, d, J = 1.8 Hz).
Add 1.5 g of 6-chloro-5-fluoronicotinic acid, 1.1 g of 2-methylcyclohexylamine, 1.5 g of 1-hydroxybenzotriazole and 2.1 g of WSC to 15 ml of DMF, 10 minutes at 130 ° C., then 1 day at room temperature Stir. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.6 g of N- (2-methylcyclohexyl) -6-chloro-5-fluoronicotinic acid amide.
N- (2-Methylcyclohexyl) -6-chloro-5-fluoronicotinic acid amide

¹ H-NMR (CDCl ₃ ) δ: 0.94 (0.9H, d, J = 6.8 Hz), 0.98 (2.1H, d, J = 6.3 Hz), 1.10-1.84 (8.0H, m), 1.97-2.08 ( 1.0H, m), 3.66-3.76 (0.7H, m), 4.24-4.30 (0.3H, m), 5.81-5.89 (0.7H, br m), 6.04-6.10 (0.3H, br m), 7.90- 7.94 (1.0H, m), 8.51-8.53 (1.0H, m).
0.40 g of N- (2-methylcyclohexyl) -6-chloro-5-fluoronicotinic acid amide, 0.25 g of propargyl alcohol and 71 mg of sodium hydride were added to 10 ml of DMF and stirred at room temperature for 8 hours. To the reaction mixture was added aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.27 g of N- (2-methylcyclohexyl) -5-fluoro-6- (2-propynyloxy) nicotinic acid amide (hereinafter referred to as the present compound 2). It was.
Compound 2 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 0.93 (0.9H, d, J = 7.1 Hz), 0.98 (2.1H, d, J = 6.3 Hz), 1.09-1.82 (8.0H, m), 1.92-2.08 ( 1.0H, m), 2.50-2.52 (1.0H, m), 3.64-3.73 (0.7H, m), 4.22-4.28 (0.3H, m), 5.09-5.10 (2.0H, m), 5.75-5.81 ( 0.7H, br m), 6.00-6.05 (0.3H, br m), 7.80-7.84 (1.0H, m), 8.31 (0.7H, d, J = 2.0 Hz), 8.32 (0.3H, d, J = 2.0 Hz).

¹H-NMR (CDCl₃) δ: 0.93 (0.9H, d, J = 6.8 Hz), 0.98 (2.1H, d, J = 6.6 Hz), 1.10-1.82 (8.0H, m), 1.90-2.09 (1.0H, m), 3.64-3.74 (0.7H, m), 4.07 (2.1H, s), 4.07 (0.9H, s), 4.22-4.29 (0.3H, m), 5.73-5.80 (0.7H, br m), 5.99-6.04 (0.3H, br m), 7.77 (1.0H, dd, J = 10.5, 2.0 Hz), 8.30 (0.7H, d, J = 2.0 Hz), 8.31 (0.3H, d, J = 2.0 Hz). Production Example 3
0.30 g of N- (2-methylcyclohexyl) -6-chloro-5-fluoronicotinic acid amide and 0.64 g of 28% sodium methoxide methanol solution were added to 4 ml of methanol, and the mixture was stirred at room temperature for 8 hours. The reaction mixture is concentrated under reduced pressure, water is added to the residue, and the resulting solid is collected by filtration, dried and dried to give N- (2-methylcyclohexyl) -5-fluoro-6-methoxynicotinic acid amide (hereinafter referred to as the present invention). This is referred to as compound 3.) 0.21 g was obtained.
Compound 3 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 0.93 (0.9H, d, J = 6.8 Hz), 0.98 (2.1H, d, J = 6.6 Hz), 1.10-1.82 (8.0H, m), 1.90-2.09 ( 1.0H, m), 3.64-3.74 (0.7H, m), 4.07 (2.1H, s), 4.07 (0.9H, s), 4.22-4.29 (0.3H, m), 5.73-5.80 (0.7H, br m), 5.99-6.04 (0.3H, br m), 7.77 (1.0H, dd, J = 10.5, 2.0 Hz), 8.30 (0.7H, d, J = 2.0 Hz), 8.31 (0.3H, d, J = 2.0 Hz).

¹H-NMR (CDCl₃) δ: 0.93 (0.9H, d, J = 6.8 Hz), 0.97 (2.1H, d, J = 6.6 Hz), 1.09-1.82 (8.0H, m), 1.91-2.07 (1.0H, m), 3.64-3.73 (0.7H, m), 4.21-4.27 (0.3H, m), 4.91 (2.0H, br s), 5.64-5.71 (0.7H, br m), 5.92-5.98 (0.3H, br m), 7.66-7.71 (1.0H, m), 8.21-8.24 (1.0H, m). Production Example 4
0.30 g of N- (2-methylcyclohexyl) -6-chloro-5-fluoronicotinic acid amide and 0.5 ml of 1,4-dioxane were added to 3 ml of 28% aqueous ammonia, and a microwave reactor (product name: Discover, CEM) was used for 10 minutes under conditions of 18 kgf / cm ² (internal temperature: about 100 ° C.). The reaction mixture was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography, and N- (2-methylcyclohexyl) -6-amino-5-fluoronicotinic acid amide (hereinafter referred to as the present compound 4). 29 g was obtained.
Compound 4 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 0.93 (0.9H, d, J = 6.8 Hz), 0.97 (2.1H, d, J = 6.6 Hz), 1.09-1.82 (8.0H, m), 1.91-2.07 ( 1.0H, m), 3.64-3.73 (0.7H, m), 4.21-4.27 (0.3H, m), 4.91 (2.0H, br s), 5.64-5.71 (0.7H, br m), 5.92-5.98 ( 0.3H, br m), 7.66-7.71 (1.0H, m), 8.21-8.24 (1.0H, m).

¹H-NMR (CDCl₃) δ: 0.94-1.31 (5H, m), 1.54-1.79 (6H, m), 3.31 (2H, dd, J = 6.5, 6.4 Hz), 6.38 (1H, br s), 7.93 (1H, dd, J = 8.0, 2.0 Hz), 8.55 (1H, d, J = 2.0 Hz).
Ｎ−（シクロヘキシルメチル）−６−クロロ−５−フルオロニコチン酸アミド０．３０ｇと２８％ナトリウムメトキシドメタノール溶液１．０ｇとを混合し、室温で８時間攪拌した。反応混合物を減圧下濃縮し、残渣に水を加えて生成した固体をろ集し、乾燥して、Ｎ−（シクロヘキシルメチル）−５−フルオロ−６−メトキシニコチン酸アミド（以下、本発明化合物５と記す。）０．２５ｇを得た。
本発明化合物５

¹H-NMR (CDCl₃) δ: 0.94-1.31 (5H, m), 1.54-1.78 (6H, m), 3.28-3.32 (2H, m), 4.07 (3H, s), 6.09 (1H, br s), 7.77 (1H, dd, J = 10.5, 2.0 Hz), 8.30 (1H, d, J = 2.0 Hz). Production Example 5
1.0 g of 6-chloro-5-fluoronicotinic acid, 0.77 g of cyclohexylmethylamine, 1.0 g of 1-hydroxybenzotriazole and 1.4 g of WSC were added to 4 ml of DMF and stirred at 130 ° C. for 10 minutes and then at room temperature for 1 day. . Saturated aqueous sodium hydrogen carbonate solution 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 residue was subjected to silica gel column chromatography to obtain 1.1 g of N- (cyclohexylmethyl) -6-chloro-5-fluoronicotinic acid amide.
N- (Cyclohexylmethyl) -6-chloro-5-fluoronicotinic acid amide

¹ H-NMR (CDCl ₃ ) δ: 0.94-1.31 (5H, m), 1.54-1.79 (6H, m), 3.31 (2H, dd, J = 6.5, 6.4 Hz), 6.38 (1H, br s), 7.93 (1H, dd, J = 8.0, 2.0 Hz), 8.55 (1H, d, J = 2.0 Hz).
0.30 g of N- (cyclohexylmethyl) -6-chloro-5-fluoronicotinic acid amide and 1.0 g of 28% sodium methoxide methanol solution were mixed and stirred at room temperature for 8 hours. The reaction mixture is concentrated under reduced pressure, water is added to the residue, and the resulting solid is collected by filtration, dried, and dried to give N- (cyclohexylmethyl) -5-fluoro-6-methoxynicotinic acid amide (hereinafter referred to as Compound 5 of the present invention). 0.25 g was obtained.
Compound 5 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 0.94-1.31 (5H, m), 1.54-1.78 (6H, m), 3.28-3.32 (2H, m), 4.07 (3H, s), 6.09 (1H, br s ), 7.77 (1H, dd, J = 10.5, 2.0 Hz), 8.30 (1H, d, J = 2.0 Hz).

¹H-NMR (CDCl₃) δ: 0.94-1.31 (5H, m), 1.53-1.78 (6H, m), 3.26-3.30 (2H, m), 4.93 (2H, br s), 6.02 (1H, br s), 7.69 (1H, dd, J = 11.2, 1.7 Hz), 8.23 (1H, s). Production Example 6
N- (cyclohexylmethyl) -6-chloro-5-fluoronicotinic acid amide (0.30 g) and 1,4-dioxane (0.5 ml) were added to 28% aqueous ammonia (3 ml), and a microwave reactor (product name: Discover, CEM) And subjected to conditions of 18 kgf / cm ² (internal temperature: about 100 ° C.) for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 78 mg of N- (cyclohexylmethyl) -6-amino-5-fluoronicotinic acid amide (hereinafter referred to as the present compound 6). .
Compound 6 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 0.94-1.31 (5H, m), 1.53-1.78 (6H, m), 3.26-3.30 (2H, m), 4.93 (2H, br s), 6.02 (1H, br s), 7.69 (1H, dd, J = 11.2, 1.7 Hz), 8.23 (1H, s).

Next, formulation examples are shown. In addition, a part represents a weight part.
Formulation Example 1
A wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of the compound 1 of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide. Each wettable powder is obtained in the same manner as described above except that the present compound 1 is replaced with any one of the present compound 2 to the present compound 6.

Formulation Example 2
20 parts of the present compound 1 and 1.5 parts of sorbitan trioleate are 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 and 0.1 part of aluminum magnesium silicate are added, and 10 parts of propylene glycol is further added and stirred to obtain a flowable preparation. Each flowable is obtained in the same manner as described above except that the compound 1 of the present invention is replaced with any one of the compound 2 of the present invention to the compound 6 of the present invention.

Formulation Example 3
By thoroughly pulverizing and mixing 2 parts of the compound 1 of the present invention, 88 parts of kaolin clay and 10 parts of talc, a powder is obtained. Each powder is obtained in the same manner as described above except that the compound 1 of the present invention is replaced with any one of the compound 2 of the present invention to the compound 6 of the present invention.

Formulation Example 4
An emulsion is obtained by thoroughly mixing 5 parts of the compound 1 of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene. Each emulsion is obtained in the same manner as described above except that the compound 1 of the present invention is replaced with any one of the compounds 2 to 6 of the present invention.

Formulation Example 5
By thoroughly pulverizing and mixing 2 parts of the compound 1 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, kneaded well with water and granulated and dried. , Get the granules. Each granule is obtained in the same manner as described above except that the present compound 1 is replaced with any one of the present compound 2 to the present compound 6.

Formulation Example 6
This invention compound 1 10 parts, polyoxyethylene alkyl ether sulfate ammonium salt 35 parts white carbon 35 parts and water 55 parts are mixed, and a flowable formulation is obtained by carrying out the fine grinding | pulverization by the wet grinding method. Each flowable is obtained in the same manner as described above except that the compound 1 of the present invention is replaced with any one of the compound 2 of the present invention to the compound 6 of the present invention.

Next, test examples show that the compound of the present invention is 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;
Cucumber gray mold prevention effect test (Botrytis cinerea)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. Each of the compounds 1 to 6 of the present invention was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a PDA medium containing spores of cucumber gray mold was placed on the cucumber leaf surface. After inoculation, the lesion area was investigated after 5 days in a humid environment at 12 ° C. As a result, the lesion area in the plant treated with the compounds 2 and 4 of the present invention was 30% or less of the lesion area in the untreated plant.

Test Example 2;
Tomato plague prevention effect test (Phytophthora infestans)
A plastic pot was filled with sand loam, seeded with tomato (variety: patio), and grown in a greenhouse for 20 days. Each of the present compounds 1 to 6 was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to adhere well to the leaf surface of the tomato seedling. After air-drying the diluted solution on the leaf surface to dryness, a water suspension of tomato blight fungus spores was spray-inoculated. After inoculation, it was first placed at 23 ° C. under high humidity for 1 day and further cultivated in a greenhouse for 4 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compounds 2, 4 and 5 of the present invention was 30% or less of the lesion area in the untreated plant.

Test Example 3;
Cucumber nuclear disease prevention effect test (Sclerotinia sclerotiorum)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. Each of the compounds 1 to 6 of the present invention was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium containing mycorrhizal fungi was placed on the cucumber leaf surface. After the inoculation, the lesion area was examined after being placed at 18 ° C. under high humidity for 4 days. As a result, the lesion area in the plant treated with the present compounds 1, 2, and 4 was 30% or less of the lesion area in the untreated plant.

Test Example 4;
Wheat leaf blight prevention effect test (Septoria tritici)
A plastic pot was filled with sandy loam, wheat (cultivar: Apogee) was sown and grown in a greenhouse for 10 days. Each of the compounds 1 to 6 of the present invention was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to adhere well to the leaf surface of the wheat. After spraying, the plants were air-dried, and after 2 days, sprayed with a water suspension of wheat leaf blight fungus spores. After the inoculation, the area was first placed under a high humidity of 18 ° C. for 3 days and further under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 2, 3 and 4 was 30% or less of the lesion area in the untreated plant.

Test Example 5
Radish black spot disease prevention effect test (Alternaria brassicicola)
A plastic pot was filled with sand loam, seeded with Japanese radish (variety; early 40 days), and grown in a greenhouse for 5 days. Each of the compounds 1 to 6 of the present invention was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to adhere well to the radish leaves. After spraying, the plants were air-dried and spray-inoculated with a water suspension of radish black spot fungus spores. After inoculation, it was first placed at 24 ° C. under high humidity for 1 day and then placed in a greenhouse for 3 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compound 6 of the present invention was 30% or less of the lesion area in the untreated plant.

Claims (6)

Formula (1)

[Where,
X ¹ represents a fluorine atom or a methoxy group,
X ² represents a methoxy group, 2-propynyloxy group, amino group, monomethylamino group or 2-propynylamino group,
Z ¹ represents an oxygen atom or a sulfur atom,
E ¹ represents a group represented by A ¹ -Cy ¹ or a group represented by A ² -CR ⁸ R ⁹ R ¹⁰ ;
A ¹ is a single bond, CH ₂ group, CH (CH ₃ ) group, C (CH ₃ ) ₂ group, CH (CH ₂ CH ₃ ) group, CH ₂ CH ₂ group, CH ₂ CH ₂ CH ₂ group or C ( A CH ₂ CH ₂ ) group, or a CH ₂ group substituted with at least one group selected from the group consisting of a C1-C3 haloalkyl group, a C2-C4 alkenyl group and a C2-C4 alkynyl group,
A ² is a CH ₂ group, a CH (CH ₃ ) group, a C (CH ₃ ) ₂ group, a CH (CH ₂ CH ₃ ) group, or a C1-C3 haloalkyl group, a C2-C4 alkenyl group, and a C2-C4 alkynyl group. Represents a CH ₂ group substituted with at least one group selected from the group consisting of:
Cy ¹ is substituted with at least one group selected from the following group [a-1], a C3-C6 cycloalkyl group optionally substituted with at least one group selected from the following group [a-1]. A C3-C6 cycloalkenyl group which may be substituted, C3 which may be substituted with at least one group selected from the following group [a-1], and one of the methylenes forming the ring is substituted with a carbonyl group A -C6 cycloalkyl group or a C3-C6 hydroxyiminocycloalkyl group optionally substituted with at least one group selected from the following group [a-1],
R ⁸ and R ⁹ independently represent a C1-C4 alkyl group,
R ¹⁰ is a hydrogen atom, C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4 alkynyl group, halogen atom, hydroxyl group, C1-C6 alkoxy group, C3-C6 alkenyloxy group, C1-C6 haloalkyl group, C2 -C6 haloalkoxy group, C1-C3 alkylthio group, hydroxy C1-C6 alkyl group, C2-C4 alkylcarbonyloxy group, (C1-C3 alkylamino) C1-C6 alkyl group, (di (C1-C3 alkyl) amino) C1-C6 alkyl group, mercapto group, C1-C3 alkylsulfonyl group or NR ¹¹ R ¹² group [wherein R ¹¹ and R ¹² independently represent a hydrogen atom or a C1-C4 alkyl group. ] Is represented.
Group [a-1]:
Halogen atom, C1-C4 alkyl group, C2-C4 alkenyl group, C2-C4 alkynyl group, hydroxyl group, C1-C6 alkoxy group, C3-C6 alkenyloxy group, C1-C6 haloalkyl group, C1-C6 haloalkoxy group, C1-C3 alkylthio group, C1-C3 alkylidene group forming a double bond with the same carbon atom forming the ring, hydroxy C1-C6 alkyl group, C2-C4 alkylcarbonyloxy group, (C1-C3 alkylamino) C1 -C6 alkyl group, (di (C1-C3 alkyl) amino) C1-C6 alkyl group, mercapto group, formyl group, C1-C3 alkylsulfonyl group or NR ¹³ R ¹⁴ group [wherein R ¹³ and R ¹⁴ are independently Represents a hydrogen atom or a C1-C4 alkyl group. ]]
An amide compound represented by The amide compound according to claim 1, wherein X ¹ is a fluorine atom. The amide compound according to claim 1 or 2, wherein E ¹ is a group represented by A ¹ -Cy ¹ . The amide compound according to claim 1 or 2, wherein E ¹ is a group represented by A ² -CR ⁸ R ⁹ R ¹⁰ .   A plant disease control agent comprising the amide compound according to any one of claims 1 to 4.   A method for controlling plant diseases, which comprises applying an effective amount of the amide compound according to any one of claims 1 to 4 to a plant or soil.