JP2010077117A - Amide compound and application thereof for plant disease control - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound exhibiting excellent control effects on plant diseases. <P>SOLUTION: The amide compound represented by formula (I) [wherein R<SP>1</SP>is a hydrogen atom or a fluorine atom; and R<SP>2</SP>is a 1-6C linear alkyl group or a linear (1-2C alkoxy)-(2-5C) alkyl group] exhibits excellent control effects on plant diseases. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

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

  Drugs for controlling plant diseases have been developed, and many compounds having a plant disease control effect have been found, but the effect may not be sufficient, and a search for new compound groups has been conducted eagerly. Yes.

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

〔式中、Ｒ¹は水素原子又はフッ素原子を表し、Ｒ²はＣ１−Ｃ６直鎖アルキル基又は直鎖式の（Ｃ１−Ｃ２アルコキシ）Ｃ２−Ｃ５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。）。
〔２〕 Ｒ¹がフッ素原子であり、Ｒ²がＣ１−Ｃ６直鎖アルキル基である〔１〕記載のアミド化合物。
〔３〕 Ｒ¹がフッ素原子であり、Ｒ²がメチル基又はエチル基である〔１〕記載のアミド化合物。
〔４〕 Ｒ¹が水素原子であり、Ｒ²がＣ１−Ｃ６直鎖アルキル基である〔１〕記載のアミド化合物。
〔５〕 Ｒ¹が水素原子であり、Ｒ²がメチル基、エチル基又はブチル基である〔１〕記載のアミド化合物。
〔６〕 Ｒ²が直鎖式の（Ｃ１−Ｃ２アルコキシ）Ｃ２−Ｃ５アルキル基である〔１〕記載のアミド化合物。
〔７〕 Ｒ¹が水素原子である〔６〕記載のアミド化合物。
〔８〕 Ｒ¹がフッ素原子である〔６〕記載のアミド化合物。
〔９〕 Ｒ²が直鎖式の（Ｃ１−Ｃ２アルコキシ）Ｃ３−Ｃ４アルキル基である〔６〕〜〔８〕いずれか一項記載のアミド化合物。
〔１０〕 〔１〕〜〔９〕いずれか一項記載のアミド化合物を有効成分として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。）。
〔１１〕 〔１〕〜〔９〕いずれか一項記載のアミド化合物の有効量を植物又は土壌に処理する工程を有してなる植物病害の防除方法（以下、本発明防除方法と記す場合もある。）。
〔１２〕 植物又は土壌に処理することにより、植物病害を防除するための〔１〕〜〔９〕いずれか一項記載のアミド化合物の使用。
〔１３〕 式（ＩＩ）

〔式中、Ｒ¹は水素原子又はフッ素原子を表す。〕
で示されるアミド化合物（以下、本アミド化合物と記す場合もある。）。 As a result of studying to find a compound having an excellent control effect against plant diseases, the present inventor has found that the amide compound represented by the following formula (I) has an excellent control effect against plant diseases. The present invention has been reached.
That is, the present invention is as follows [1] to [13].
[1] Formula (I)

[Wherein, R ¹ represents a hydrogen atom or a fluorine atom, and R ² represents a C1-C6 linear alkyl group or a linear (C1-C2 alkoxy) C2-C5 alkyl group. ]
An amide compound represented by the formula (hereinafter sometimes referred to as the present compound).
[2] The amide compound according to [1], wherein R ¹ is a fluorine atom and R ² is a C1-C6 straight chain alkyl group.
[3] The amide compound according to [1], wherein R ¹ is a fluorine atom and R ² is a methyl group or an ethyl group.
[4] The amide compound according to [1], wherein R ¹ is a hydrogen atom, and R ² is a C1-C6 linear alkyl group.
[5] The amide compound according to [1], wherein R ¹ is a hydrogen atom and R ² is a methyl group, an ethyl group or a butyl group.
[6] The amide compound according to [1], wherein R ² is a linear (C1-C2 alkoxy) C2-C5 alkyl group.
[7] The amide compound according to [6], wherein R ¹ is a hydrogen atom.
[8] The amide compound according to [6], wherein R ¹ is a fluorine atom.
[9] The amide compound according to any one of [6] to [8], wherein R ² is a linear (C1-C2 alkoxy) C3-C4 alkyl group.
[10] A plant disease control agent comprising the amide compound according to any one of [1] to [9] as an active ingredient (hereinafter sometimes referred to as the present invention control agent).
[11] A method for controlling plant diseases comprising a step of treating the plant or soil with an effective amount of the amide compound according to any one of [1] to [9] (hereinafter also referred to as the present invention control method). is there.).
[12] Use of the amide compound according to any one of [1] to [9] for controlling plant diseases by treating the plant or soil.
[13] Formula (II)

[Wherein, R ¹ represents a hydrogen atom or a fluorine atom. ]
An amide compound represented by (hereinafter sometimes referred to as the present amide compound).

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

In the present invention, the “straight chain (C1-C2 alkoxy) C2-C5 alkyl group” represented by R ² represents a (C1-C2 alkoxy) C2-C5 alkyl group in which the carbon chain is not branched.

In the present invention, examples of the C1-C6 linear alkyl group represented by R ² include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
(C1-C2 alkoxy) As C2-C5 alkyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 4-methoxybutyl group, 4-ethoxybutyl group, Examples include 5-methoxypentyl group and 5-ethoxypentyl group.

As an aspect of this invention compound, the following are mentioned, for example.
An amide compound in which R ¹ is a hydrogen atom in formula (I);
An amide compound in which R ¹ is a fluorine atom in formula (I);
An amide compound represented by formula (I), wherein R ² is a C1-C6 linear alkyl group;
An amide compound in which R ² is a methyl group, an ethyl group or a butyl group in formula (I);
An amide compound in which R ² is a methyl group or an ethyl group in formula (I);
An amide compound in which R ² is a straight-chain (C1-C2 alkoxy) C2-C5 alkyl group in formula (I);
An amide compound represented by formula (I), wherein R ² is a linear methoxy C2-C5 alkyl group;
An amide compound represented by formula (I), wherein R ² is a linear ethoxy C2-C5 alkyl group;
An amide compound represented by formula (I), wherein R ¹ is a hydrogen atom and R ² is a C1-C6 linear alkyl group;
An amide compound represented by formula (I), wherein R ¹ is a fluorine atom and R ² is a C1-C6 linear alkyl group;
An amide compound in which R ¹ is a hydrogen atom and R ² is a methyl group, an ethyl group or a butyl group in formula (I);
An amide compound in which R ¹ is a fluorine atom and R ² is a methyl group or an ethyl group in formula (I);
An amide compound represented by formula (I), wherein R ¹ is a hydrogen atom, and R ² is a linear (C1-C2 alkoxy) C2-C5 alkyl group;
An amide compound in which R ¹ is a fluorine atom and R ² is a linear (C1-C2 alkoxy) C2-C5 alkyl group in formula (I);
An amide compound in which R ¹ is a hydrogen atom and R ² is a linear methoxy C2-C3 alkyl group in formula (I);
An amide compound represented by formula (I), wherein R ¹ is a fluorine atom and R ² is a linear methoxy C2-C3 alkyl group;
An amide compound represented by formula (I), wherein R ¹ is a hydrogen atom and R ² is a linear ethoxy C2-C3 alkyl group;
An amide compound represented by the formula (I), wherein R ¹ is a fluorine atom and R ² is a linear ethoxy C2-C3 alkyl group.

The manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by the following (Production Method 1) to (Production Method 3).

〔式中、Ｒ¹及びＲ²は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
該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。）、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。）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。）等の酸アミド類、ジメチルスルホキシド（以下、ＤＭＳＯと記す。）等のスルホキシド類、ピリジン等の含窒素芳香族化合物類等及びこれらの混合物が挙げられる。
該反応に用いられる脱水縮合剤としては、例えば１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩（以下、ＷＳＣと記す。）、１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、及び（ベンゾトリアゾール−１−イルオキシ）トリス（ジメチルアミノ）ホスホニウムヘキサフルオロホスフェート（以下、ＢＯＰ試薬と記す。）が挙げられる。
該反応では化合物（ＩＩＩ）１モルに対して化合物（ＩＶ）が通常０．５〜３モルの割合、化合物（ＩＩＩ）１モルに対して脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常−２０℃〜１４０℃の範囲である。該反応の反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加えた際、固体が析出した場合は、濾過することにより本発明化合物を単離することができる。反応混合物に水を加えた際に固体が析出しない場合は、反応混合物と水との混合物を有機溶媒で抽出し、有機層を乾燥、濃縮することにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 1)
The compound of the present invention is produced by reacting compound (III) or a salt thereof (for example, hydrochloride and hydrobromide) with compound (IV) in the presence of a dehydration condensing agent. Can do.

[Wherein, R ¹ and R ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether (hereinafter referred to as MTBE), hexane, heptane, octane and the like. Aliphatic hydrocarbons, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, N, N-dimethylformamide (hereinafter, And acid amides such as dimethyl sulfoxide (hereinafter referred to as DMSO), nitrogen-containing aromatic compounds such as pyridine, and the like, and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC), 1,3-dicyclohexylcarbodiimide, and ( Benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (hereinafter referred to as BOP reagent).
In this reaction, compound (IV) is usually used in a proportion of 0.5 to 3 mol per 1 mol of compound (III), and a dehydrating condensing agent is usually used in a proportion of 1 to 5 mol per 1 mol of compound (III). .
The reaction temperature of the reaction is usually in the range of -20 ° C to 140 ° C. The reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, when water is added to the reaction mixture, if a solid is precipitated, the compound of the present invention can be isolated by filtration. When solid does not precipitate when water is added to the reaction mixture, the compound of the present invention can be isolated by extracting the mixture of the reaction mixture and water with an organic solvent, and drying and concentrating the organic layer. . The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

〔式中、Ｒ¹及びＲ²は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
該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及びこれらの混合物が挙げられる。
該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が挙げられる。
該反応では化合物（Ｖ）１モルに対して化合物（ＩＩＩ）が通常０．５〜３モルの割合、化合物（Ｖ）１モルに対して塩基が通常１〜５モルの割合で用いられる。
該反応の反応温度は通常−２０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加えた際に固体が析出した場合は、濾過することにより本発明化合物を単離することができる。反応混合物に固体が析出しない場合は、反応混合物と水との混合物を有機溶媒で抽出し、有機層を乾燥、濃縮することにより、本発明化合物を単離することができる。単離された本発明化合物を、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 2)
The compound of the present invention can be produced by reacting compound (III) or a salt thereof (for example, hydrochloride and hydrobromide) with compound (V) in the presence of a base. .

[Wherein, R ¹ and R ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and chlorobenzene. Examples thereof include halogenated hydrocarbons, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, 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. Can be mentioned.
In the reaction, compound (III) is usually used in a proportion of 0.5 to 3 mol per mol of compound (V), and base is usually used in a proportion of 1 to 5 mol per mol of compound (V).
The reaction temperature is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, when a solid is precipitated when water is added to the reaction mixture, the compound of the present invention can be isolated by filtration. When a solid does not precipitate in the reaction mixture, the compound of the present invention can be isolated by extracting the mixture of the reaction mixture and water with an organic solvent, drying and concentrating the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

〔式中、Ｒ¹及びＲ²は前記と同じ意味を表し、Ｌは塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基又はｐ−トルエンスルホニルオキシ基を表す。〕
該反応は、通常溶媒の存在下で行われる。
該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、クロロベンゼン等のハロゲン化炭化水素類、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、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、水及びこれらの混合物が挙げられる。
該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、水酸化ナトリウム等のアルカリ金属水酸化物類及び水素化ナトリウム等のアルカリ金属水素化物類が挙げられる。
該反応では化合物（ＩＩ）１モルに対して化合物（ＶＩ）が通常１〜１０モルの割合、化合物（ＩＩ）１モルに対して塩基が通常１〜５モルの割合で用いられる。
該反応の反応温度は通常−２０〜１００℃の範囲である。該反応の反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加えた際に、固体が析出した場合は、濾過することにより本発明化合物を単離することができる。反応混合物に水を加えた際に固体が析出しない場合は、反応混合物と水との混合物を有機溶媒で抽出し、有機層を乾燥、濃縮することにより、本発明化合物を単離することができる。単離された本発明化合物を、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 3)
The compound of the present invention can be produced by reacting the present amide compound and compound (VI) in the presence of a base.

[Wherein R ¹ and R ² represent the same meaning as described above, and L represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, or a p-toluenesulfonyloxy group. ]
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, nitriles such as acetonitrile, DMF, and the like. Acid amides, sulfoxides such as DMSO, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydroxides such as sodium hydroxide, and alkali metal hydrides such as sodium hydride. .
In the reaction, compound (VI) is usually used in a proportion of 1 to 10 mol per mol of compound (II), and base is usually used in a proportion of 1 to 5 mol per mol of compound (II).
The reaction temperature is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, when a solid is precipitated when water is added to the reaction mixture, the compound of the present invention can be isolated by filtration. When solid does not precipitate when water is added to the reaction mixture, the compound of the present invention can be isolated by extracting the mixture of the reaction mixture and water with an organic solvent, and drying and concentrating the organic layer. . The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

  Next, the production of the present amide compound is shown in the synthesis examples.

〔式中、Ｒ¹は前記と同じ意味を表し、Ｚはｔｅｒｔ−ブチルジメチルシリル基、メチル基、メトキシメチル基、ベンジル基、アセチル基等の保護基を表す。〕
Ｚがｔｅｒｔ−ブチルジメチルシリル基の場合、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、クロロベンゼン等のハロゲン化炭化水素類、アセトニトリル等のニトリル類、ＤＭＦ等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、水及びこれらの混合物が挙げられる。
脱保護反応に用いられる塩基やフッ化物としては、水酸化リチウム、水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物類、フッ化ナトリウム、フッ化テトラブチルアンモニウム、フッ化水素酸等のフッ素化合物が挙げられる。
化合物（ＶＩＩ）１モルに対して、塩基やフッ化物が通常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、反応混合物に水を加え、これをＭＴＢＥ、ヘキサン等の有機溶媒で洗浄することにより得られる水層に、塩酸、酢酸等の酸を加えて酸性とした後、有機溶媒抽出、濃縮等の後処理を行うことにより、本アミド化合物を単離することができる。単離された本アミド化合物はクロマトグラフィー、再結晶等によりさらに精製することもできる。 (Synthesis example)
This amide compound can be manufactured by deprotecting the protecting group of compound (VII).

[Wherein, R ¹ represents the same meaning as described above, and Z represents a protecting group such as a tert-butyldimethylsilyl group, a methyl group, a methoxymethyl group, a benzyl group, or an acetyl group. ]
When Z is a tert-butyldimethylsilyl group, 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, nitriles such as acetonitrile, and DMF. Examples thereof include acid amides, sulfoxides such as dimethyl sulfoxide, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, water, and mixtures thereof.
Examples of bases and fluorides used in the deprotection reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, fluorine such as sodium fluoride, tetrabutylammonium fluoride and hydrofluoric acid. Compounds.
The base or fluoride is usually used at a ratio of 1 to 10 moles with respect to 1 mole of the compound (VII).
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, water is added to the reaction mixture, and the resulting aqueous layer is washed with an organic solvent such as MTBE and hexane, acidified with an acid such as hydrochloric acid and acetic acid, extracted with an organic solvent, The amide compound can be isolated by post-treatment such as concentration. The isolated present amide compound can be further purified by chromatography, recrystallization and the like.

Specific examples of the compound of the present invention include N-benzothiazol-6-yl-2- (2-fluoro-3-methoxyphenyl) acetamide, N-benzothiazol-6-yl-2- (3-ethoxy- 2-Fluorophenyl) acetamide, N-benzothiazol-6-yl-2- (2-fluoro-3-propoxyphenyl) acetamide, N-benzothiazol-6-yl-2- (3-butoxy-2-fluorophenyl) ) Acetamide, N-benzothiazol-6-yl-2- (2-fluoro-3-pentyloxyphenyl) acetamide, N-benzothiazol-6-yl-2- (2-fluoro-3-hexyloxyphenyl) acetamide ,
N-benzothiazol-6-yl-2- (3-methoxyphenyl) acetamide, N-benzothiazol-6-yl-2- (3-ethoxyphenyl) acetamide, N-benzothiazol-6-yl-2- ( 3-propoxyphenyl) acetamide, N-benzothiazol-6-yl-2- (3-butoxyphenyl) acetamide, N-benzothiazol-6-yl-2- (3-pentyloxyphenyl) acetamide, N-benzothiazole -6-yl-2- (3-hexyloxyphenyl) acetamide,
N-benzothiazol-6-yl-2- (3- (2-methoxyethoxy) phenyl) acetamide, N-benzothiazol-6-yl-2- (3- (2-ethoxyethoxy) phenyl) acetamide, N- Benzothiazol-6-yl-2- (3- (3-methoxypropoxy) phenyl) acetamide, N-benzothiazol-6-yl-2- (3- (3-ethoxypropoxy) phenyl) acetamide, N-benzothiazole -6-yl-2- (3- (4-methoxybutoxy) phenyl) acetamide, N-benzothiazol-6-yl-2- (3- (4-ethoxybutoxy) phenyl) acetamide, N-benzothiazole-6 -Yl-2- (3- (5-methoxypentyloxy) phenyl) acetamide, N-benzothiazole-6- Ru-2- (3- (5-ethoxypentyloxy) phenyl) acetamide, N-benzothiazol-6-yl-2- (2-fluoro-3- (2-methoxyethoxy) phenyl) acetamide, N-benzothiazole -6-yl-2- (3- (2-ethoxyethoxy) -2-fluorophenyl) acetamide, N-benzothiazol-6-yl-2- (2-fluoro-3- (3-methoxypropoxy) phenyl) Acetamide, N-benzothiazol-6-yl-2- (3- (3-ethoxypropoxy) -2-fluorophenyl) acetamide, N-benzothiazol-6-yl-2- (2-fluoro-3- (4 -Methoxybutoxy) phenyl) acetamide, N-benzothiazol-6-yl-2- (3- (4-ethoxybutoxy) -2- Fluorophenyl) acetamide, N-benzothiazol-6-yl-2- (2-fluoro-3- (5-methoxypentyloxy) phenyl) acetamide and N-benzothiazol-6-yl-2- (3- (5- And ethoxypentyloxy) -2-fluorophenyl) acetamide.

  The control agent of the present invention contains the compound of the present invention and an inert carrier. Examples of the inert carrier include a solid carrier, a liquid carrier, and a gas carrier. The control agent of the present invention is usually further added with auxiliary agents for formulation such as surfactant, fixing agent, dispersant, stabilizer, etc., and wettable powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion. It is formulated into aqueous liquids, oils, smokes, aerosols, microcapsules and the like. The present control agent contains the present compound in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.

  Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like. Hydrogens (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexane, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, , Acetonitrile, isobutylnitrile), ethers (eg Dioxane, diisopropyl ether), acid amides (e.g., DMF, dimethylacetamide), halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, and carbon tetrachloride), and the like.

  Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.

  Other formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.

  Examples of the method of using the control agent of the present invention for controlling plant diseases include treatment of plant bodies such as foliage spraying, treatment of plant cultivation sites such as soil treatment, and treatment of seeds such as seed disinfection. It is done.

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, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole , Diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole , Microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, i Azole fungicides such as imazalil, flutriafol, simeconazole, ipconazole; cyclic amines such as fenpropimorph, tridemorph, fenpropidin Bactericidal compounds; benzimidazole bactericidal compounds such as carbendazim, benomyl, thiabendazole, thiophanate-methyl; procymidone; cyprodinil; pyrimethanil; dietofencarb (Diethofencarb); thiuram; fluazinam; mancozeb; iprodione (mancozeb); vinclozolin; chlorothalonil; captan; mepa Nipipromim; fenpiclonil; fludioxonil; diclofluranid; folpet; kresoxim-methyl; azoxystrobin; trifloxystrobin Fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; metminostrobin; enestroburin; spiroxamine (Spiroxamine); quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; etaboxam; amisulbrom; Benproviacarb; Benthiavalicarb; Cyazofamid; Mandipropamid; Boscalid; Penthiopyrad; Metrafenone; fluopyram; fluopyramix; Cyflufenamid (cyflufenamid); proquinazid (proquinazid); oryzastrobin (orysastrobin); furametpyr; furametpyr; thifluzamide; mepronil; flutolanil; flusulfamide (flusulfamide); metalaxyl M); kiralaxyl; fosetyl; cymoxanil; pencycuron; tolclofos-methyl; carpropamid Dicoxymet; phenoxanil; tricyclazole; pyroquilon; probenazole; isotianil; tiadinil; tebufroquin; tebufroquin; Ferimzone; fthalide; validamycin; hydroxyisoxazole; iminoctadin-acetate; isoprothiolane; oxolinic acid; oxytetracycline; Streptomycin, sedaxane; isopyrazam; BYF-14182; flutianil; basic copper chloride; cupric hydroxide (c upric hydroxide); basic copper sulfate; organic copper; sulfur.

Examples of such other insecticides include (1) organophosphorus compounds such as acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos. (Ch1orfenvinphos), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl, cyanophos (CYAP), diazinon (diazinon), DCIP (dichlorodiisopropyl ether), dichlorfenthion (ECP), dichlorvos (DDVP), dimethophos (Dimethoate), dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion (MPP), fenitrothion (MEP), phosti Azate (fosthiazate), formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion (DMTP), monocrotophos (monocrotophos) , Naled (BRP), oxydeprofos (ESP), parathion, parathion, phosalone, phosmet (PMP), pyrimiphos-methy1, pyridafenthion, quinalphos , Phenthoate (PAP), profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temepho s), tetrach1orvinphos, terbufos, thiometon, trichlorphon (DEP), bamidomion, phorate, cadusafos, etc .;
(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbfuran, carbosulfan, cloethocarb, ethiofencarb ), Fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb (MIPC), metolcarb, metomyl, methiocarb, NAC, oxamyl (amyl) ), Pirimicarb, propoxur (PHC), XMC, thiodicarb, xylylcarb, aldicarb, etc .;
(3) Synthetic pyrethroid compounds acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin (cyfluthrin) cyhalothrin), cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenthrinate Prox (flufenoprox), flumethrin, fluvalinate, halfenprox (halfenprox), imiprothrin, permethrin, praretrin (pi) Threin (pyrethrins), resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, othrin , Cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, furamethrin, tau-fluvalinate, 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- Tylbenzyl (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, bensult (bensu1tap), thiocyclam, monosultap, bisultap, etc .;
(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamiprid), thiamethoxam (thiamethoxam), thiacloprid, dinotefuran, clothianidin, etc .;
(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoc Flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron, etc .;
(7) Phenylpyrazole compounds Acetoprole, ethiprole, 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, methoxyfenozide, tebufenozide and the like;
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, etc .;
(11) Natural insecticide machine oil, nicotine-sulfate;
(12) Other insecticides avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyromazine, DD (1,3-Dichloropropene), emamectin benzoate ( emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, metoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine , Pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, subpimectin Arsenic acid, Benclothiaz, Calcium cyanamide, Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flonicamid (Flurimfen), formetanate, metam-ammonium, metam-sodium, methyl bromide, nidinotefuran, potassium oleate, prototri Fenbute, spiromesifen, sulfur, metaflumizone, spirotetramat, pyrifluquinazone, spinetram, chlorantraniliprole, cyan Traniliprol cyantraniliprole)
And the like.
Examples of such other acaricides (acaricidal active ingredients) include, for example, acequinocyl, amitraz, benzoximate, bifenaate, phenisobromolate, quinomethionat , Chlorobenzilate, CPCBS (chlorfenson), clofentezine, cyflumetofen, kelofol, etoxazole, fenbutatin oxide, fenothiocarb, fenpyroxycarb (Fenpyroximate), fluacrypyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactins, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cyenopyrafen, etc. It is done.
Examples of such other nematicides (nematicidal active ingredients) include, for example, DCIP, fosthiazate, levamisol hydrochloride, methamiisothiocyanate, morantel tartarate, imicyafos Etc.

The control method of the present invention includes a step of treating an effective amount of the compound of the present invention with a plant or soil. This invention control method is normally performed by processing this invention control agent to a plant or soil.
The amount of the present control agent used in the present control method varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc. The amount of the invention compound is usually 1 to 500 g, preferably ^{2 to} 200 g per 1000 m ² . Emulsions, wettable powders, suspensions and the like are usually diluted with water and applied. 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 1. The powder, granules and the like are usually applied as they are without dilution. In the treatment of seeds, the amount of the compound of the present invention in the control agent of the present invention is usually 0.001 to 100 g, preferably 0.01 to 50 g, per 1 kg of seed.

  The control agent of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards. The control agent of the present invention can control diseases of the farmland in the farmland 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.,
Bridegroom,
Foliage plant,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, umes, 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 '' is resistant 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 a “crop” to which resistance has been imparted by a classic breeding method, imidazolinone herbicide-resistant Clearfield (registered trademark) canola, such as imazetapil, and sulfonylurea-based ALS-inhibiting herbicide resistance such as thifensulfuron methyl There are STS soybeans. In addition, examples of “crop” to which tolerance has been imparted by genetic engineering techniques include glyphosate and glufosinate-resistant corn varieties that have already been sold under trade names such as RoundupReady (registered trademark) and LibertyLink (registered trademark). Yes.

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

Moreover, as toxins expressed in such genetically modified crops, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, δ-endotoxin proteins such as Cry3Bb1 or Cry9C, and insecticidal protein hybrids such as 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 technology. 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 expressing Cry1Ab toxin), YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1 Corn varieties that express toxins), Herculex I® (corn varieties that express phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties expressing), Bollgard I (registered trademark) (cotton varieties expressing Cry1Ac toxin), Bollgard II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxin), VIPCOT (registered trademark) (VIP toxin) Cotton varieties), NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin), NatureGard (registered trademark) Agrisure (registered trademark) GT Advant Examples include age (GA21 glyphosate resistance trait), Agrisure (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 and calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.) are known. 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 No. 03/000906)) and other anti-pathogenic substances produced by microorganisms.

Examples of plant diseases that can be controlled by the present invention include filamentous fungi and the like, and more specifically, the following diseases can be mentioned, but are not limited thereto.
Usually, this invention control method is performed by using this invention control agent by the method of applying this invention control agent mentioned above.

  Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat powdery mildew ( Erysiphe graminis), red mold (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronectriella nivalis), Bare Scab (Ustilago tritici, U. nuda), Tilletia caries, Eye spot disease (Pseudocercosporella herpotrichoides), Cloud disease (Rhynchosporium secalis), Leaf blight (Septoria tritici), Blight (Leptosphaeria nodorum), net blotch (Pyrenophora teres Drechsler), blight (Gaeumannomyces graminis), maculopathy (Pyrenophora tritici-repentis); citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot Disease (Penicillium digitatum, P. italicum); apple Monilinia mali, rot (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf (Alternaria alternata apple pathotype), black star (Venturia inaequalis), anthrax Disease (Glomerella cingulata); pear black spot disease (Venturia nashicola, V. pirina), black spot disease (Alternaria alternata Japanese pear pathotype), red star disease (Gymnosporangium haraeanum); peach blight (Monilinia fructicola), black star disease ( Cladosporium carpophilum), Phomopsis sp .; Grapes black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black lot disease ( Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kaki), defoliation (Cercospora kaki, Mycosphaerella nawae); cucurbit anthracnose (Colletotrichum lagen) arium), powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.), seedling blight (Pythium sp. ); Tomato ring-rot (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans); eggplant brown rot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); Disease (Alternaria japonica), white spot disease (Cercosporella brassicae), root-knot disease (Plasmodiophora parasitica), downy mildew (Peronospora parasitica); leek rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae), rust (Phakopsora pachyrhizi), bean anthracnose (Colletotrichum lindemthianum) groundnut black rot (Cercospora personata), brown spot (Cercospora ara) chidicola), white silkworm (Sclerotium rolfsii); pea powdery mildew (Erysiphe pisi); potato summer plague (Alternaria solani), plague (Phytophthora infestans), half body wilt (Verticillium albo-atrum, V. dahliae, V nigrescens); Strawberry powdery mildew (Sphaerotheca humuli); Cha net wilt (Exobasidium reticulatum); White spot disease (Elsinoe leucospila), Ring spot disease (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis) tobacco Red Star Disease (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae); brown spot of sugar beet (Cercospora beticola), leaf rot Disease (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces sochlioides); rose black spot disease (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); chrysanthemum leaf spot (Septoria chrys) anthemi-indici), white rust (Puccinia horiana); onion white spot blight (Botrytis cinerea, B. byssoidea, B. squamosa), gray rot (Botrytis alli); bacterium rot (Botrytis squamosa) Various crops of gray mold disease (Botrytis cinerea), sclerotia disease (Sclerotinia sclerotiorum); radish black spot disease (Alternaria brassicicola); buckwheat dollar spot disease (Sclerotinia homeocarpa), buckwheat brown patch disease and large patch disease ( Rhizoctonia solani); and banana Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).

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: 3.80 (2H, d, J = 1.4 Hz), 3.91 (3H, s), 6.93-6.98 (2H, m), 7.09-7.14 (1H, m), 7.23-7.27 (1H, m), 7.47 (1H, br s), 8.00 (1H, d, J = 8.7 Hz), 8.50 (1H, d, J = 2.2 Hz), 8.91 (1H, s). Production Example 1
0.18 g of 6-aminobenzothiazole, 0.20 g of 2-fluoro-3-methoxyphenylacetic acid, 0.20 g of 1-hydroxybenzotriazole, 0.30 g of WSC and 0.30 g of pyridine were added to 2 ml of DMF, and 140 ° C. for 5 minutes. Stir at room temperature for 8 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give N-benzothiazol-6-yl-2- (2-fluoro-3-methoxyphenyl) acetamide (hereinafter referred to as the present compound (1)). 27 g was obtained.
Compound (1) of the present invention

¹ H-NMR (CDCl ₃ ) δ: 3.80 (2H, d, J = 1.4 Hz), 3.91 (3H, s), 6.93-6.98 (2H, m), 7.09-7.14 (1H, m), 7.23-7.27 (1H, m), 7.47 (1H, br s), 8.00 (1H, d, J = 8.7 Hz), 8.50 (1H, d, J = 2.2 Hz), 8.91 (1H, s).

¹H-NMR (DMSO-D₆)δ: 1.34 (3H, t, J = 7.0 Hz), 3.76 (2H, s), 4.09 (2H, q, J = 7.0 Hz), 6.91-6.95 (1H, m), 7.05-7.07 (2H, m), 7.61 (1H, dd, J = 8.9, 2.1 Hz), 8.02 (1H, d, J = 8.8 Hz), 8.52 (1H, d, J = 2.0 Hz), 9.26 (1H, s), 10.49 (1H, s). Production Example 2
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide, 0.18 g of iodoethane and 7 ml of DMF, 0.34 g of cesium carbonate was added and stirred at room temperature for 4 hours. . Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to give N-benzothiazol-6-yl-2- (2-fluoro-3-ethoxyphenyl) acetamide (hereinafter referred to as the present compound ( 2). 0.16 g was obtained.
Compound (2) of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 1.34 (3H, t, J = 7.0 Hz), 3.76 (2H, s), 4.09 (2H, q, J = 7.0 Hz), 6.91-6.95 (1H, m ), 7.05-7.07 (2H, m), 7.61 (1H, dd, J = 8.9, 2.1 Hz), 8.02 (1H, d, J = 8.8 Hz), 8.52 (1H, d, J = 2.0 Hz), 9.26 (1H, s), 10.49 (1H, s).

¹H-NMR (DMSO-D₆) δ: 0.98 (3H, t, J = 7.4 Hz), 1.70-1.79 (2H, m), 3.76 (2H, s), 3.99 (2H, t, J = 6.5 Hz), 6.90-6.96 (1H, m), 7.04-7.09 (2H, m), 7.60 (1H, dd, J = 8.8, 2.0 Hz), 8.02 (1H, d, J = 8.8 Hz), 8.52 (1H, d, J = 2.2 Hz), 9.26 (1H, s), 10.49 (1H, s). Production Example 3
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide, 0.15 g of iodopropane and 5 ml of DMF, 0.26 g of cesium carbonate was added and stirred at room temperature for 4 hours. did. Ice water was added to the reaction mixture, and the precipitated solid was collected by filtration, and N-benzothiazol-6-yl-2- (2-fluoro-3-propoxyphenyl) acetamide (hereinafter referred to as the present compound (3)). 0.18 g was obtained.
Compound (3) of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 0.98 (3H, t, J = 7.4 Hz), 1.70-1.79 (2H, m), 3.76 (2H, s), 3.99 (2H, t, J = 6.5 Hz ), 6.90-6.96 (1H, m), 7.04-7.09 (2H, m), 7.60 (1H, dd, J = 8.8, 2.0 Hz), 8.02 (1H, d, J = 8.8 Hz), 8.52 (1H, d, J = 2.2 Hz), 9.26 (1H, s), 10.49 (1H, s).

¹H-NMR (DMSO-D₆) δ: 0.93 (3H, t, J = 7.5 Hz), 1.39-1.49 (2H, m), 1.67-1.74 (2H, m), 3.76 (2H, s), 4.03 (2H, t, J = 6.3 Hz), 6.90-6.95 (1H, m), 7.03-7.09 (2H, m), 7.60 (1H, dd, J = 9.2, 1.7 Hz), 8.02 (1H, d, J = 8.7 Hz), 8.52 (1H, d, J = 1.7 Hz), 9.26 (1H, s), 10.48 (1H, s). Production Example 4
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide, 0.22 g of iodobutane and 7 ml of DMF, 0.37 g of cesium carbonate was added and stirred at room temperature for 4 hours. . Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with hexane, and 0.15 g of N-benzothiazol-6-yl-2- (2-fluoro-3-butoxyphenyl) acetamide (hereinafter referred to as the present compound (4)) was obtained. Obtained.
The present compound (4)

¹ H-NMR (DMSO-D ₆ ) δ: 0.93 (3H, t, J = 7.5 Hz), 1.39-1.49 (2H, m), 1.67-1.74 (2H, m), 3.76 (2H, s), 4.03 (2H, t, J = 6.3 Hz), 6.90-6.95 (1H, m), 7.03-7.09 (2H, m), 7.60 (1H, dd, J = 9.2, 1.7 Hz), 8.02 (1H, d, J = 8.7 Hz), 8.52 (1H, d, J = 1.7 Hz), 9.26 (1H, s), 10.48 (1H, s).

¹H-NMR (DMSO-D₆) δ: 0.89 (3H, t, J = 6.8 Hz), 1.30-1.45 (4H, m), 1.69-1.77 (2H, m), 3.76 (2H, s), 4.03 (2H, t, J = 6.4 Hz), 6.90-6.97 (1H, m), 7.04-7.10 (2H, m), 7.61 (1H, d, J = 8.7 Hz), 8.02 (1H, d, J = 8.9 Hz), 8.53 (1H, s), 9.26 (1H, s), 10.48 (1H, s). Production Example 5
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide, 0.17 g of iodopentane and 5 ml of DMF, 0.26 g of cesium carbonate was added and stirred at room temperature for 4 hours. did. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with hexane, and 0.15 g of N-benzothiazol-6-yl-2- (2-fluoro-3-pentyloxyphenyl) acetamide (hereinafter referred to as the present compound (5)). Got.
Compound (5) of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 0.89 (3H, t, J = 6.8 Hz), 1.30-1.45 (4H, m), 1.69-1.77 (2H, m), 3.76 (2H, s), 4.03 (2H, t, J = 6.4 Hz), 6.90-6.97 (1H, m), 7.04-7.10 (2H, m), 7.61 (1H, d, J = 8.7 Hz), 8.02 (1H, d, J = 8.9 Hz), 8.53 (1H, s), 9.26 (1H, s), 10.48 (1H, s).

¹H-NMR (DMSO-D₆)δ: 0.87 (3H, t, J = 7.0 Hz), 1.26-1.34 (4H, m), 1.37-1.46 (2H, m), 1.67-1.76 (2H, m), 3.76 (2H, s), 4.02 (2H, t, J = 6.5 Hz), 6.89-6.96 (1H, m), 7.03-7.09 (2H, m), 7.60 (1H, dd, J = 8.8, 2.1 Hz), 8.02 (1H, d, J = 8.7 Hz), 8.52 (1H, d, J = 2.2 Hz), 9.26 (1H, s), 10.48 (1H, s). Production Example 6
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide, 0.22 g of 1-bromohexane and 5 ml of DMF, 0.43 g of cesium carbonate was added, and 4 Stir for hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with hexane, and 0.14 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hexyloxyphenyl) acetamide (hereinafter referred to as the present compound (6)). Got.
The present compound (6)

¹ H-NMR (DMSO-D ₆ ) δ: 0.87 (3H, t, J = 7.0 Hz), 1.26-1.34 (4H, m), 1.37-1.46 (2H, m), 1.67-1.76 (2H, m) , 3.76 (2H, s), 4.02 (2H, t, J = 6.5 Hz), 6.89-6.96 (1H, m), 7.03-7.09 (2H, m), 7.60 (1H, dd, J = 8.8, 2.1 Hz ), 8.02 (1H, d, J = 8.7 Hz), 8.52 (1H, d, J = 2.2 Hz), 9.26 (1H, s), 10.48 (1H, s).

¹H-NMR (CDCl₃) δ: 3.77 (2H, s), 3.84 (3H, s), 6.88-6.96 (3H, m), 7.19 (1H, dd, J = 8.9, 2.1 Hz), 7.27-7.38 (2H, m), 7.99 (1H, d, J = 8.9 Hz), 8.49 (1H, d, J = 2.1 Hz), 8.90 (1H, s). Production Example 7
0.15 g of 6-aminobenzothiazole, 0.20 g of 3-methoxyphenylacetic acid, 0.15 g of 1-hydroxybenzotriazole, 0.25 g of WSC and 0.35 g of pyridine are added to 2 ml of DMF, and the mixture is at 140 ° C. for 5 minutes and at room temperature for 8 hours. Stir. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with water, aqueous sodium hydrogen carbonate solution, MTBE and hexane to give N- (benzothiazol-6-yl) -2- (3-methoxyphenyl) acetamide (hereinafter referred to as the present compound (7)). 0.25 g was obtained.
Compound (7) of the present invention

¹ H-NMR (CDCl ₃ ) δ: 3.77 (2H, s), 3.84 (3H, s), 6.88-6.96 (3H, m), 7.19 (1H, dd, J = 8.9, 2.1 Hz), 7.27-7.38 (2H, m), 7.99 (1H, d, J = 8.9 Hz), 8.49 (1H, d, J = 2.1 Hz), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 1.43 (3H, t, J = 7.0 Hz), 3.75 (2H, s), 4.05 (2H, q, J = 7.0 Hz), 6.88-6.93 (3H, m), 7.18 (1H, dd, J = 8.8, 2.1 Hz), 7.23 (1H, s), 7.33 (1H, dd, J = 8.9, 7.5 Hz), 7.98 (1H, d, J = 8.7 Hz), 8.50 (1H, d, J = 2.2 Hz), 8.90 (1H, s). Production Example 8
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.14 g of 1-iodoethane and 5 ml of DMF, 0.28 g of cesium carbonate was added and stirred at room temperature for 2.5 hours. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed in turn with an aqueous sodium hydroxide solution, water and hexane, and then washed with N-benzothiazol-6-yl-2- (3-ethoxyphenyl) -acetamide (hereinafter referred to as the following). This is referred to as the present compound (8).) 0.17 g was obtained.
Compound (8) of the present invention

¹ H-NMR (CDCl ₃ ) δ: 1.43 (3H, t, J = 7.0 Hz), 3.75 (2H, s), 4.05 (2H, q, J = 7.0 Hz), 6.88-6.93 (3H, m), 7.18 (1H, dd, J = 8.8, 2.1 Hz), 7.23 (1H, s), 7.33 (1H, dd, J = 8.9, 7.5 Hz), 7.98 (1H, d, J = 8.7 Hz), 8.50 (1H , d, J = 2.2 Hz), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 1.05 (3H, t, J = 7.5 Hz), 1.78-1.87 (2H, m), 3.76 (2H, s), 3.94 (2H, t, J = 6.5 Hz), 6.89-6.93 (3H, m), 7.18 (1H, dd, J = 8.8, 2.1 Hz), 7.28 (1H, s), 7.31-7.35 (1H, m), 7.99 (1H, d, J = 8.9 Hz), 8.49 (1H, d, J = 2.2 Hz), 8.90 (1H, s). Production Example 9
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.11 g of 1-bromopropane and 5 ml of DMF, 0.28 g of cesium carbonate was added and stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed successively with an aqueous sodium hydroxide solution, water and hexane, and then washed with N-benzothiazol-6-yl-2- (3-propoxyphenyl) -acetamide (hereinafter referred to as the following). This is referred to as the present compound (9).) 0.13 g was obtained.
Compound (9) of the present invention

¹ H-NMR (CDCl ₃ ) δ: 1.05 (3H, t, J = 7.5 Hz), 1.78-1.87 (2H, m), 3.76 (2H, s), 3.94 (2H, t, J = 6.5 Hz), 6.89-6.93 (3H, m), 7.18 (1H, dd, J = 8.8, 2.1 Hz), 7.28 (1H, s), 7.31-7.35 (1H, m), 7.99 (1H, d, J = 8.9 Hz) , 8.49 (1H, d, J = 2.2 Hz), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 0.98 (3H, t, J = 7.3 Hz), 1.45-1.55 (2H, m), 1.74-1.81 (2H, m), 3.76 (2H, s), 3.98 (2H, t, J = 6.5 Hz), 6.88-6.93 (3H, m), 7.18 (1H, dd, J = 8.8, 2.2 Hz), 7.23 (1H, s), 7.33 (1H, dd, J = 9.0, 7.6 Hz), 7.99 (1H, d, J = 8.8 Hz), 8.50 (1H, d, J = 2.0 Hz), 8.90 (1H, s). Production Example 10
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.13 g of 1-bromobutane and 5 ml of DMF, 0.28 g of cesium carbonate was added and stirred at room temperature for 5 hours. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed successively with an aqueous sodium hydroxide solution, water and hexane, and then washed with N-benzothiazol-6-yl-2- (3-butoxyphenyl) -acetamide (hereinafter referred to as the following). This is referred to as the present compound (10).) 0.15 g was obtained.
Compound (10) of the present invention

¹ H-NMR (CDCl ₃ ) δ: 0.98 (3H, t, J = 7.3 Hz), 1.45-1.55 (2H, m), 1.74-1.81 (2H, m), 3.76 (2H, s), 3.98 (2H , t, J = 6.5 Hz), 6.88-6.93 (3H, m), 7.18 (1H, dd, J = 8.8, 2.2 Hz), 7.23 (1H, s), 7.33 (1H, dd, J = 9.0, 7.6 Hz), 7.99 (1H, d, J = 8.8 Hz), 8.50 (1H, d, J = 2.0 Hz), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 0.93 (3H, t, J = 7.0 Hz), 1.34-1.48 (4H, m), 1.76-1.83 (2H, m), 3.75 (2H, s), 3.97 (2H, t, J = 6.6 Hz), 6.88-6.92 (3H, m), 7.17-7.20 (1H, m), 7.23 (1H, s), 7.31-7.35 (1H, m), 7.98 (1H, d, J = 8.7 Hz), 8.50 (1H, s), 8.90 (1H, s). Production Example 11
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.18 g of 1-iodopentane and 5 ml of DMF, 0.28 g of cesium carbonate was added and stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed in turn with an aqueous sodium hydroxide solution, water and hexane, and then washed with N-benzothiazol-6-yl-2- (3-pentyloxyphenyl) -acetamide (hereinafter referred to as “the acetamide”). This is referred to as the present compound (11).) 0.18 g was obtained.
Compound (11) of the present invention

¹ H-NMR (CDCl ₃ ) δ: 0.93 (3H, t, J = 7.0 Hz), 1.34-1.48 (4H, m), 1.76-1.83 (2H, m), 3.75 (2H, s), 3.97 (2H , t, J = 6.6 Hz), 6.88-6.92 (3H, m), 7.17-7.20 (1H, m), 7.23 (1H, s), 7.31-7.35 (1H, m), 7.98 (1H, d, J = 8.7 Hz), 8.50 (1H, s), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 0.89-0.92 (3H, m), 1.32-1.36 (4H, m), 1.43-1.50 (2H, m), 1.75-1.82 (2H, m), 3.76 (2H, s), 3.97 (2H, t, J = 6.6 Hz), 6.88-6.93 (3H, m), 7.18 (1H, dd, J = 8.8, 2.1 Hz), 7.29 (1H, s), 7.33 (1H, dd, J = 8.9, 7.5 Hz), 7.99 (1H, d, J = 8.7 Hz), 8.49 (1H, d, J = 1.9 Hz), 8.90 (1H, s). Production Example 12
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.15 g of 1-bromohexane and 5 ml of DMF, 0.28 g of cesium carbonate was added and stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed in turn with an aqueous sodium hydroxide solution, water and hexane, and then washed with N-benzothiazol-6-yl-2- (3-hexyloxyphenyl) -acetamide (hereinafter referred to as “the reaction mixture”). This is referred to as the present compound (12).) 0.17 g was obtained.
The present compound (12)

¹ H-NMR (CDCl ₃ ) δ: 0.89-0.92 (3H, m), 1.32-1.36 (4H, m), 1.43-1.50 (2H, m), 1.75-1.82 (2H, m), 3.76 (2H, s), 3.97 (2H, t, J = 6.6 Hz), 6.88-6.93 (3H, m), 7.18 (1H, dd, J = 8.8, 2.1 Hz), 7.29 (1H, s), 7.33 (1H, dd , J = 8.9, 7.5 Hz), 7.99 (1H, d, J = 8.7 Hz), 8.49 (1H, d, J = 1.9 Hz), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 2.03-2.09 (2H, m), 3.35 (3H, s), 3.56 (2H, t, J = 6.1 Hz), 3.75 (2H, s), 4.08 (2H, t, J = 6.3 Hz), 6.89-6.94 (3H, m), 7.19 (1H, dd, J = 8.8, 2.2 Hz), 7.29 (1H, s), 7.33 (1H, dd, J = 9.0, 7.6 Hz), 7.99 (1H, d, J = 8.5 Hz), 8.49 (1H, d, J = 2.0 Hz), 8.90 (1H, s). Production Example 13
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.14 g of 1-bromo-3-methoxypropane and 5 ml of DMF, 0.28 g of cesium carbonate was added, and the mixture was stirred at room temperature. Stir for half an hour. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed successively with aqueous sodium hydroxide solution, water and hexane to give N-benzothiazol-6-yl-2- (3- (3-methoxypropoxy) phenyl). 0.17 g of acetamide (hereinafter referred to as the present compound (13)) was obtained.
Compound (13) of the present invention

¹ H-NMR (CDCl ₃ ) δ: 2.03-2.09 (2H, m), 3.35 (3H, s), 3.56 (2H, t, J = 6.1 Hz), 3.75 (2H, s), 4.08 (2H, t , J = 6.3 Hz), 6.89-6.94 (3H, m), 7.19 (1H, dd, J = 8.8, 2.2 Hz), 7.29 (1H, s), 7.33 (1H, dd, J = 9.0, 7.6 Hz) , 7.99 (1H, d, J = 8.5 Hz), 8.49 (1H, d, J = 2.0 Hz), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 1.73-1.79 (2H, m), 1.84-1.91 (2H, m), 3.35 (3H, s), 3.45 (2H, t, J = 6.3 Hz), 3.75 (2H, s), 4.01 (2H, t, J = 6.2 Hz), 6.88-6.93 (3H, m), 7.19 (1H, dd, J = 8.8, 2.0 Hz), 7.28 (1H, s), 7.31-7.35 (1H, m), 7.99 (1H, d, J = 8.8 Hz), 8.49 (1H, d, J = 1.5 Hz), 8.90 (1H, s). Production Example 14
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.17 g of 4-methoxybutylmethanesulfonate and 5 ml of DMF, 0.28 g of cesium carbonate was added, and the mixture was stirred at room temperature for 7 hours and a half. Stir. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed successively with aqueous sodium hydroxide solution, water and hexane to give N-benzothiazol-6-yl-2- (3- (4-methoxybutoxy) phenyl). 0.091 g of acetamide (hereinafter referred to as the present compound (14)) was obtained.
The present compound (14)

¹ H-NMR (CDCl ₃ ) δ: 1.73-1.79 (2H, m), 1.84-1.91 (2H, m), 3.35 (3H, s), 3.45 (2H, t, J = 6.3 Hz), 3.75 (2H , s), 4.01 (2H, t, J = 6.2 Hz), 6.88-6.93 (3H, m), 7.19 (1H, dd, J = 8.8, 2.0 Hz), 7.28 (1H, s), 7.31-7.35 ( 1H, m), 7.99 (1H, d, J = 8.8 Hz), 8.49 (1H, d, J = 1.5 Hz), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J = 7.0 Hz), 2.03-2.09 (2H, m), 3.50 (2H, q, J = 7.0 Hz), 3.60 (2H, t, J = 6.1 Hz), 3.75 (2H, s), 4.09 (2H, t, J = 6.2 Hz), 6.90-6.93 (3H, m), 7.18 (1H, d, J = 9.0 Hz), 7.27 (1H, s), 7.33 (1H, t, J = 8.0 Hz), 7.99 (1H, d, J = 8.5 Hz), 8.49 (1H, s), 8.90 (1H, s). Production Example 15
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.17 g of 3-ethoxypropanemethanesulfonate and 5 ml of DMF, 0.28 g of cesium carbonate was added, and the mixture was stirred at room temperature for 7 and a half hours. Stir. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed successively with aqueous sodium hydroxide solution, water and hexane to give N-benzothiazol-6-yl-2- (3- (3-ethoxypropoxy) phenyl). 0.087 g of acetamide (hereinafter referred to as the present compound (15)) was obtained.
The present compound (15)

¹ H-NMR (CDCl ₃ ) δ: 1.20 (3H, t, J = 7.0 Hz), 2.03-2.09 (2H, m), 3.50 (2H, q, J = 7.0 Hz), 3.60 (2H, t, J = 6.1 Hz), 3.75 (2H, s), 4.09 (2H, t, J = 6.2 Hz), 6.90-6.93 (3H, m), 7.18 (1H, d, J = 9.0 Hz), 7.27 (1H, s ), 7.33 (1H, t, J = 8.0 Hz), 7.99 (1H, d, J = 8.5 Hz), 8.49 (1H, s), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J = 7.0 Hz), 1.73-1.80 (2H, m), 1.85-1.91 (2H, m), 3.46-3.51 (4H, m), 3.76 (2H, s), 4.01 (2H, t, J = 6.4 Hz), 6.88-6.93 (3H, m), 7.18 (1H, dd, J = 8.9, 2.2 Hz), 7.27 (1H, s), 7.33 (1H, dd, J = 9.1, 7.6 Hz), 7.99 (1H, d, J = 8.9 Hz), 8.49 (1H, d, J = 1.9 Hz), 8.90 (1H, s). Production Example 16
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.25 g of 4-ethoxybutyl paratoluenesulfonate and 5 ml of DMF, 0.28 g of cesium carbonate was added, and the mixture was stirred at room temperature for 4 hours. Stir. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed successively with aqueous sodium hydroxide solution, water and hexane to give N-benzothiazol-6-yl-2- (3- (4-ethoxybutoxy) phenyl). 0.080 g of acetamide (hereinafter referred to as the present compound (16)) was obtained.
Compound (16) of the present invention

¹ H-NMR (CDCl ₃ ) δ: 1.20 (3H, t, J = 7.0 Hz), 1.73-1.80 (2H, m), 1.85-1.91 (2H, m), 3.46-3.51 (4H, m), 3.76 (2H, s), 4.01 (2H, t, J = 6.4 Hz), 6.88-6.93 (3H, m), 7.18 (1H, dd, J = 8.9, 2.2 Hz), 7.27 (1H, s), 7.33 ( 1H, dd, J = 9.1, 7.6 Hz), 7.99 (1H, d, J = 8.9 Hz), 8.49 (1H, d, J = 1.9 Hz), 8.90 (1H, s).

¹H-NMR (DMSO-D₆) δ: 1.92-1.99 (2H, m), 3.25 (3H, s), 3.47 (2H, t, J = 6.3 Hz), 3.76 (2H, s), 4.08 (2H, t, J = 6.3 Hz), 6.91-6.97 (1H, m), 7.04-7.10 (2H, m), 7.61 (1H, dd, J = 8.8, 2.1 Hz), 8.02 (1H, d, J = 8.9 Hz), 8.53 (1H, d, J = 1.9 Hz), 9.26 (1H, s), 10.49 (1H, s). Production Example 17
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide, 0.20 g of 1-bromo-3-methoxypropane and 5 ml of DMF, 0.43 g of cesium carbonate was added. And stirred at room temperature for 4 hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give N-benzothiazol-6-yl-2- (2-fluoro-3- (3-methoxypropoxy) phenyl) acetamide (hereinafter referred to as the present compound (17)). 0.10 g was obtained.
The present compound (17)

¹ H-NMR (DMSO-D ₆ ) δ: 1.92-1.99 (2H, m), 3.25 (3H, s), 3.47 (2H, t, J = 6.3 Hz), 3.76 (2H, s), 4.08 (2H , t, J = 6.3 Hz), 6.91-6.97 (1H, m), 7.04-7.10 (2H, m), 7.61 (1H, dd, J = 8.8, 2.1 Hz), 8.02 (1H, d, J = 8.9 Hz), 8.53 (1H, d, J = 1.9 Hz), 9.26 (1H, s), 10.49 (1H, s).

¹H-NMR (DMSO-D₆) δ: 1.10 (3H, t, J = 6.5 Hz), 1.91-1.99 (2H, m), 3.42 (2H, q, J = 7.0 Hz), 3.51 (2H, t, J = 6.3 Hz), 3.76 (2H, s), 4.09 (2H, t, J = 6.2 Hz), 6.91-6.96 (1H, m), 7.04-7.10 (2H, m), 7.60 (1H, d, J = 8.9 Hz), 8.02 (1H, d, J = 8.7 Hz), 8.53 (1H, s), 9.26 (1H, s), 10.48 (1H, s). Production Example 18
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide, 0.22 g of 3-ethoxypropanemethanesulfonate and 7 ml of DMF, 0.37 g of cesium carbonate was added, and For 4 hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography and concentrated. The obtained residue was washed with MTBE, and N-benzothiazol-6-yl-2- (2-fluoro-3- (3-ethoxypropoxy) 0.09 g of phenyl) acetamide (hereinafter referred to as the present compound (18)) was obtained.
Compound (18) of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 1.10 (3H, t, J = 6.5 Hz), 1.91-1.99 (2H, m), 3.42 (2H, q, J = 7.0 Hz), 3.51 (2H, t , J = 6.3 Hz), 3.76 (2H, s), 4.09 (2H, t, J = 6.2 Hz), 6.91-6.96 (1H, m), 7.04-7.10 (2H, m), 7.60 (1H, d, J = 8.9 Hz), 8.02 (1H, d, J = 8.7 Hz), 8.53 (1H, s), 9.26 (1H, s), 10.48 (1H, s).

1H-NMR (DMSO-D₆) δ: 1.60-1.70 (2H, m), 1.72-1.80 (2H, m), 3.23 (3H, s), 3.37 (2H, t, J = 6.3 Hz), 3.76 (2H, s), 4.04 (2H, t, J = 6.3 Hz), 6.90-6.97 (1H, m), 7.04-7.10 (2H, m), 7.60 (1H, dd, J = 8.7, 1.9 Hz), 8.02 (1H, d, J = 8.9 Hz), 8.53 (1H, s), 9.26 (1H, s), 10.47 (1H, s). Production Example 19
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide, 0.22 g of 4-methoxybutylmethanesulfonate and 7 ml of DMF, 0.37 g of cesium carbonate was added, and For 4 hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with hexane, and N-benzothiazol-6-yl-2- (2-fluoro-3- (4-methoxybutoxy) phenyl) acetamide (hereinafter referred to as the present compound (19)). 0.16 g was obtained.
Compound (19) of the present invention

1H-NMR (DMSO-D ₆ ) δ: 1.60-1.70 (2H, m), 1.72-1.80 (2H, m), 3.23 (3H, s), 3.37 (2H, t, J = 6.3 Hz), 3.76 ( 2H, s), 4.04 (2H, t, J = 6.3 Hz), 6.90-6.97 (1H, m), 7.04-7.10 (2H, m), 7.60 (1H, dd, J = 8.7, 1.9 Hz), 8.02 (1H, d, J = 8.9 Hz), 8.53 (1H, s), 9.26 (1H, s), 10.47 (1H, s).

1H-NMR (CDCl3) δ: 1.23 (3H, t, J = 6.9 Hz), 3.60 (2H, q, J = 7.0 Hz), 3.71 (2H, s), 3.79 (2H, t, J = 4.8 Hz), 4.11 (2H, t, J = 4.8 Hz), 6.86-6.92 (3H, m), 7.23 (1H, dd, J = 8.7, 1.9 Hz), 7.26-7.31 (1H, m), 7.73 (1H, s), 7.96 (1H, d, J = 8.7 Hz), 8.47 (1H, d, J = 2.2 Hz), 8.88 (1H, s). Production Example 20
To a mixture of 0.20 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide, 0.25 g of 1-bromo-2-ethoxyethane and 5 ml of DMF, 0.52 g of cesium carbonate was added, and the mixture was heated at 60 ° C. Stir for 2 hours. The reaction mixture was allowed to cool to near room temperature, ice water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.12 g of N-benzothiazol-6-yl-2- (2-ethoxyethoxyphenyl) acetamide (hereinafter referred to as the present compound (20)). It was.
Compound (20) of the present invention

1H-NMR (CDCl3) δ: 1.23 (3H, t, J = 6.9 Hz), 3.60 (2H, q, J = 7.0 Hz), 3.71 (2H, s), 3.79 (2H, t, J = 4.8 Hz) , 4.11 (2H, t, J = 4.8 Hz), 6.86-6.92 (3H, m), 7.23 (1H, dd, J = 8.7, 1.9 Hz), 7.26-7.31 (1H, m), 7.73 (1H, s ), 7.96 (1H, d, J = 8.7 Hz), 8.47 (1H, d, J = 2.2 Hz), 8.88 (1H, s).

  Next, the production of the present amide compound is shown in the synthesis examples.

¹H-NMR (DMSO-D₆) δ: 3.73 (2H, s), 6.75-6.95 (3H, m), 7.61 (1H, dd, J = 8.8, 1.6 Hz), 8.02 (1H, d, J = 8.7 Hz), 8.53 (1H, d, J = 1.9 Hz), 9.26 (1H, s), 9.75 (1H, s), 10.46 (1H, s). Synthesis example 1
A mixture of 5.8 g of N-benzothiazol-6-yl-2- (2-fluoro-3- (tert-butyldimethylsilyloxy) phenyl) acetamide, 1.8 g of lithium hydroxide monohydrate and 60 ml of DMF at room temperature. Stir for 5 hours. Ice water was added to the reaction mixture and washed with MTBE. 2N hydrochloric acid was added to the aqueous layer to adjust the pH to around 2, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with hexane to obtain 3.4 g of N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide.
N-benzothiazol-6-yl-2- (2-fluoro-3-hydroxyphenyl) acetamide

¹ H-NMR (DMSO-D ₆ ) δ: 3.73 (2H, s), 6.75-6.95 (3H, m), 7.61 (1H, dd, J = 8.8, 1.6 Hz), 8.02 (1H, d, J = 8.7 Hz), 8.53 (1H, d, J = 1.9 Hz), 9.26 (1H, s), 9.75 (1H, s), 10.46 (1H, s).

¹H-NMR (DMSO-D₆) δ: 3.58 (2H, s), 6.63-6.65 (1H, m), 6.75-6.77 (2H, m), 7.11 (1H, t, J = 7.9 Hz), 7.59-7.61 (1H, m), 8.01 (1H, d, J = 8.8 Hz), 8.54 (1H, s), 9.25 (1H, s), 9.34 (1H, s), 10.41 (1H, s). Synthesis example 2
A mixture of 7.8 g of 3-tert-butyldimethylsilyloxyphenylacetic acid, 4.0 g of 6-aminobenzothiazole, 7.4 ml of triethylamine, 14 g of BOP reagent and 150 ml of DMF was stirred at room temperature for 3 hours. 3% hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with 3% hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Subsequently, a mixture of the obtained residue, 3.4 g of lithium hydroxide monohydrate and 100 ml of DMF was stirred at room temperature for 5 hours. Water was added to the reaction mixture and washed with MTBE. The aqueous layer was adjusted to pH = 2 by adding 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with hexane to obtain 6.8 g of N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide.
N-benzothiazol-6-yl-2- (3-hydroxyphenyl) acetamide

¹ H-NMR (DMSO-D ₆ ) δ: 3.58 (2H, s), 6.63-6.65 (1H, m), 6.75-6.77 (2H, m), 7.11 (1H, t, J = 7.9 Hz), 7.59 -7.61 (1H, m), 8.01 (1H, d, J = 8.8 Hz), 8.54 (1H, s), 9.25 (1H, s), 9.34 (1H, s), 10.41 (1H, s).

  Next, reference production examples are shown for the production of the production intermediate of the compound of the present invention.

¹H-NMR (CDCl₃) δ: 3.89 (3H, s), 4.76 (2H, s), 6.92 (1H, td, J = 8.1, 1.6 Hz), 6.97-7.01 (1H, m), 7.08 (1H, td, J = 7.9, 1.4 Hz). Reference production example 1
A mixture of 20 g of 2-fluoro-3-methoxybenzaldehyde, 2.4 g of sodium borohydride and 200 ml of methanol was stirred at room temperature for 30 minutes. Water and 5% hydrochloric acid were sequentially added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 20 g of (2-fluoro-3-methoxyphenyl) methanol.
(2-Fluoro-3-methoxyphenyl) methanol

¹ H-NMR (CDCl ₃ ) δ: 3.89 (3H, s), 4.76 (2H, s), 6.92 (1H, td, J = 8.1, 1.6 Hz), 6.97-7.01 (1H, m), 7.08 (1H , td, J = 7.9, 1.4 Hz).

¹H-NMR (CDCl₃) δ: 3.77 (2H, s), 3.90 (3H, s), 6.94-7.03 (2H, m), 7.11 (1H, td, J = 8.0, 1.5 Hz). Reference production example 2
A mixture of 20 g of (2-fluoro-3-methoxyphenyl) methanol, 16 g of methanesulfonyl chloride and 200 ml of THF was mixed with 22 ml of triethylamine at 0 ° C. and stirred at 0 ° C. for 30 minutes. Water and 5% hydrochloric acid were sequentially added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was mixed with 200 ml of DMF, 50 ml of water and 8.3 g of sodium cyanide, and heated to reflux for 8 hours. Water was added to the reaction mixture allowed to cool to around room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with water, successively with 5% hydrochloric acid and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 12 g of (2-fluoro-3-methoxyphenyl) acetonitrile.
(2-Fluoro-3-methoxyphenyl) acetonitrile

¹ H-NMR (CDCl ₃ ) δ: 3.77 (2H, s), 3.90 (3H, s), 6.94-7.03 (2H, m), 7.11 (1H, td, J = 8.0, 1.5 Hz).

¹H-NMR (DMSO-D₆) δ: 3.56 (2H, s), 6.68-6.72 (1H, m), 6.82-6.92 (2H, m), 9.73 (1H, s), 12.40 (1H, s). Reference production example 3
100% of 48% hydrobromic acid was added to 10 g of (2-fluoro-3-methoxyphenyl) acetonitrile, and the mixture was heated to reflux for 4 hours. Next, 20 ml of 48% hydrobromic acid was added to the reaction mixture, and the mixture was heated to reflux for 4 hours. The reaction mixture allowed to cool to near room temperature was concentrated under reduced pressure, ethyl acetate and hexane were added, and the mixture was filtered. The filtrate was concentrated under reduced pressure to obtain 9.3 g of 2-fluoro-3-hydroxyphenylacetic acid.
2-Fluoro-3-hydroxyphenylacetic acid

¹ H-NMR (DMSO-D ₆ ) δ: 3.56 (2H, s), 6.68-6.72 (1H, m), 6.82-6.92 (2H, m), 9.73 (1H, s), 12.40 (1H, s) .

¹H-NMR (CDCl₃) δ: 0.21 (6H, s), 1.01 (9H, s), 3.78 (2H, d, J = 1.5 Hz), 6.89-6.97 (2H, m), 7.01-7.05 (1H, m), 7.22 (1H, dd, J = 8.8, 2.2 Hz), 7.42 (1H, s), 8.00 (1H, d, J = 8.8 Hz), 8.51 (1H, d, J = 2.0 Hz), 8.90 (1H, s). Reference production example 4
9.2 g of 2-fluoro-3-hydroxyphenylacetic acid, 19 g of tert-butyldimethylsilyl chloride, 11 g of imidazole and 150 ml of DMF were mixed and stirred at room temperature for 8 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography. Next, 8.8 g of the obtained residue, 6.0 g of 6-aminobenzothiazole, 13 ml of triethylamine, 18 g of BOP reagent and 100 ml of DMF were mixed and stirred at room temperature for 8 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 5.8 g of N-benzothiazol-6-yl-2- (2-fluoro-3- (tert-butyldimethylsilyloxy) phenyl) acetamide.
N-benzothiazol-6-yl-2- (2-fluoro-3- (tert-butyldimethylsilyloxy) phenyl) acetamide

¹ H-NMR (CDCl ₃ ) δ: 0.21 (6H, s), 1.01 (9H, s), 3.78 (2H, d, J = 1.5 Hz), 6.89-6.97 (2H, m), 7.01-7.05 (1H , m), 7.22 (1H, dd, J = 8.8, 2.2 Hz), 7.42 (1H, s), 8.00 (1H, d, J = 8.8 Hz), 8.51 (1H, d, J = 2.0 Hz), 8.90 (1H, s).

¹H-NMR (CDCl₃) δ: 3.89 (3H, s), 6.93-6.99 (1H, m), 7.04-7.10 (1H, m), 7.26-7.31 (1H, m), 7.53-7.55 (1H, m). Reference production example 5
To a mixture of 3.0 g of 2-fluoro-3-methoxybenzaldehyde and 150 ml of chloroform was added 9.7 g of carbon tetrabromide and a triphenylphosphine-chloroform solution (a solution comprising 15.3 g of triphenylphosphine and 150 ml of chloroform) at 0 ° C. The solution was added dropwise successively and stirred at room temperature for 1 day. The reaction mixture was filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 6.1 g of methyl (2-fluoro-3- (2,2-dibromoethenyl) phenyl) ether.
Methyl (2-fluoro-3- (2,2-dibromoethenyl) phenyl) ether

¹ H-NMR (CDCl ₃ ) δ: 3.89 (3H, s), 6.93-6.99 (1H, m), 7.04-7.10 (1H, m), 7.26-7.31 (1H, m), 7.53-7.55 (1H, m).

¹H-NMR (CDCl₃) δ: 1.41-1.62 (2H, m), 1.81-1.98 (2H, m), 3.37-3.59 (4H, m), 3.65-3.74 (2H, m), 3.88 (3H, s), 6.84-6.95 (2H, m), 6.99-7.05 (1H, m). Reference production example 6
Methyl (2-fluoro-3- (2,2-dibromoethenyl) phenyl) ether (6.1 g) and water (4 ml) were added to pyrrolidine (40 ml), and the mixture was stirred at room temperature for 1 day. The reaction mixture was concentrated under reduced pressure, diluted hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 4.5 g of N- (2- (2-fluoro-3-methoxyphenyl) acetyl) pyrrolidine. .
N- (2- (2-fluoro-3-methoxyphenyl) acetyl) pyrrolidine

¹ H-NMR (CDCl ₃ ) δ: 1.41-1.62 (2H, m), 1.81-1.98 (2H, m), 3.37-3.59 (4H, m), 3.65-3.74 (2H, m), 3.88 (3H, s), 6.84-6.95 (2H, m), 6.99-7.05 (1H, m).

¹H-NMR (CDCl₃) δ: 3.71 (2H, d, J = 1.7 Hz), 3.88 (3H, s), 6.81-6.85 (1H, m), 6.88-6.93 (1H, m), 7.01-7.06 (1H, m). Reference production example 7
4.5 g of N- (2- (2-fluoro-3-methoxyphenyl) acetyl) pyrrolidine, 3.0 g of 10N hydrochloric acid and 12 g of water were added to 15 ml of 1,4-dioxane, and the mixture was heated to reflux for 18 hours. The reaction mixture was allowed to cool to near room temperature and extracted with ethyl acetate, and the organic layer was extracted with aqueous sodium hydroxide. The resulting aqueous layer was acidified with hydrochloric acid and extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was washed with hexane to obtain 1.8 g of 2-fluoro-3-methoxyphenylacetic acid.
2-Fluoro-3-methoxyphenylacetic acid

¹ H-NMR (CDCl ₃ ) δ: 3.71 (2H, d, J = 1.7 Hz), 3.88 (3H, s), 6.81-6.85 (1H, m), 6.88-6.93 (1H, m), 7.01-7.06 (1H, m).

¹H-NMR (CDCl₃) δ: 0.19 (6H, s), 0.98 (9H, s), 3.57 (2H, s), 6.72-6.75 (1H, m), 6.79-6.80 (1H, m), 6.88 (1H, d, J = 7.6 Hz), 7.17 (1H, t, J = 7.9 Hz). Reference production example 8
A mixture of 10 g of 3-hydroxyphenylacetic acid, tert-butyldimethylsilyl chloride, 26 g, 27 g of potassium carbonate and 200 ml of DMF was stirred at room temperature for 2 hours and then at 80 ° C. for 4 hours. Water was added to the reaction mixture allowed to cool to around room temperature, and the mixture was washed with MTBE. Subsequently, 5% hydrochloric acid was added to the aqueous layer to adjust to pH = 3, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with hexane to obtain 15 g of 3-tert-butyldimethylsilyloxyphenylacetic acid.
3-tert-butyldimethylsilyloxyphenylacetic acid

¹ H-NMR (CDCl ₃ ) δ: 0.19 (6H, s), 0.98 (9H, s), 3.57 (2H, s), 6.72-6.75 (1H, m), 6.79-6.80 (1H, m), 6.88 (1H, d, J = 7.6 Hz), 7.17 (1H, t, J = 7.9 Hz).

  Next, formulation examples are shown. In addition, a part represents a weight part.

Formulation Example 1
The wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of the present compounds (1) to (20), 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide.

Formulation Example 2
After 20 parts of the present compounds (1) to (20) and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and pulverized by a wet pulverization method. Into this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and mixed by stirring to obtain a flowable preparation.

Formulation Example 3
By thoroughly pulverizing and mixing 2 parts of the compounds (1) to (20) of the present invention, 88 parts of kaolin clay and 10 parts of talc, a powder is obtained.

Formulation Example 4
By thoroughly mixing 5 parts of the compounds (1) to (20) of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene, an emulsion is obtained.

Formulation Example 5
2 parts of the present compounds (1) to (20), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, and then kneaded well with water, Granules are obtained by granulating and drying.

Formulation Example 6
This invention compound (1)-(20) 10 parts, polyoxyethylene alkyl ether sulfate ammonium salt 50 parts of white carbon 35 parts and water 55 parts are mixed, and a formulation is obtained by pulverizing by a wet grinding method. .

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

Test example 1
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The compounds (1) to (5), (7) to (13), (17), (18) and (19) of the present invention were formulated according to Formulation Example 6, and the concentration of the active ingredient was 500 ppm with water. Diluted to The foliage was sprayed so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of cucumber sclerotia bacterium 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 compounds (1) to (5), (7) to (13), (17), (18) and (19) of the present invention is the lesion spot in the untreated plant. It was 10% or less of the area.

Test example 2
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The compounds (14), (15) and (16) of the present invention were formulated according to Formulation Example 6 and then diluted with water so that the concentration of the active ingredient was 200 ppm. The foliage was sprayed so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of cucumber sclerotia bacterium 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 compounds (14), (15) and (16) of the present invention was 10% or less of the lesion area in the untreated plant.

Test example 3
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The compounds (1), (7), (10), (11) and (12) of the present invention were formulated according to Formulation Example 6 and then diluted with water so that the active ingredient concentration was 500 ppm. This diluted solution was sprayed on the foliage so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a spore-containing PDA medium of Botrytis cinerea was placed on the cucumber leaf surface. After inoculation, the lesion area was examined after 5 days in a humid environment at 12 ° C. As a result, the lesion area in the plant treated with the compounds (1), (7), (10), (11) and (12) of the present invention was 10% or less of the lesion area in the untreated plant. .

Test example 4
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The compounds (15) and (16) of the present invention were formulated according to Formulation Example 6 and then diluted with water so that the active ingredient concentration was 200 ppm. This diluted solution was sprayed on the foliage so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a spore-containing PDA medium of Botrytis cinerea 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 (15) and (16) of the present invention was 30% or less of the lesion area in the untreated plant.

Test Example 5
A plastic pot was filled with floor soil, rice (variety: Nipponbare) was sown, and grown in a greenhouse for 12 days. The compounds (2) and (7) of the present invention were formulated according to Formulation Example 6 and then diluted with water so that the active ingredient concentration was 500 ppm. This diluted solution was sprayed on the foliage so as to adhere sufficiently to the leaf surface of the rice. After spraying, the plants were air-dried, and a pot having rice blast (Magnaporthe grisea) diseased leaves was left around the sprayed plants. All the rice plants were placed under high humidity only at night, and the lesion area was examined 5 days after the inoculation. As a result, the lesion area in the plant treated with the compounds (2) and (7) of the present invention was 10% or less of the lesion area in the untreated plant.

Claims (13)

Formula (I)

[Wherein, R ¹ represents a hydrogen atom or a fluorine atom, and R ² represents a C1-C6 linear alkyl group or a linear (C1-C2 alkoxy) C2-C5 alkyl group. ]
An amide compound represented by The amide compound according to claim 1, wherein R ¹ is a fluorine atom and R ² is a C1-C6 linear alkyl group. The amide compound according to claim 1, wherein R ¹ is a fluorine atom, and R ² is a methyl group or an ethyl group. The amide compound according to claim ¹ , wherein R ¹ is a hydrogen atom, and R ² is a C1-C6 straight chain alkyl group. The amide compound according to claim ¹ , wherein R ¹ is a hydrogen atom and R ² is a methyl group, an ethyl group or a butyl group. The amide compound according to claim 1, wherein R ² is a linear (C1-C2 alkoxy) C2-C5 alkyl group. The amide compound according to claim 6, wherein R ¹ is a hydrogen atom. The amide compound according to claim 6, wherein R ¹ is a fluorine atom. The amide compound according to any one of claims 6 to 8, wherein R ² is a linear (C1-C2 alkoxy) C3-C4 alkyl group.   The plant disease control agent which contains the amide compound as described in any one of Claims 1-9 as an active ingredient.   A method for controlling plant diseases comprising a step of treating an effective amount of the amide compound according to any one of claims 1 to 9 to a plant or soil.   Use of the amide compound as described in any one of Claims 1-9 for controlling a plant disease by processing to a plant or soil. Formula (II)

[Wherein, R ¹ represents a hydrogen atom or a fluorine atom. ]
An amide compound represented by