JP2010285351A - Amide compound and use thereof - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound having an excellent control potency against plant diseases. <P>SOLUTION: There is provided the amide compound represented by formula (1) [wherein, R<SP>1</SP>is H, F, 1C-3C alkyl or (1C-3C alkoxy) 1C-3C alkyl; R<SP>2</SP>is H, halogen atom, 1C-3C alkyl, 1C-3C alkoxy, trifluoromethyl or trifluoromethoxy]. The amide compound has an excellent control potency against plant diseases. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

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

が知られている（例えば、特許文献１参照。）。 Many compounds have been developed and put into practical use as active ingredients of plant disease control agents. However, these compounds may not always show sufficient control efficacy.
On the other hand, N- (3-phenoxyphenyl) methyl-2-amino-nicotinic acid amide (a compound represented by the following formula (A)).

Is known (for example, see Patent Document 1).

International Publication No. 2005/033079 Pamphlet

  The present invention provides a compound having an excellent control effect against plant diseases.

〔式中、
Ｒ¹は水素原子、フッ素原子、Ｃ１−Ｃ３アルキル基又は（Ｃ１−Ｃ３アルコキシ）Ｃ１−Ｃ３アルキル基を表し、
Ｒ²は水素原子、ハロゲン原子、Ｃ１−Ｃ３アルキル基、Ｃ１−Ｃ３アルコキシ基、トリフルオロメチル基又はトリフルオロメトキシ基を表す。〕
で示されるアミド化合物。
〔２〕 Ｒ²が３位に結合したトリフルオロメチル基、４位に結合したトリフルオロメチル基、３位に結合したトリフルオロメトキシ基又は４位に結合したトリフルオロメトキシ基である〔１〕に記載のアミド化合物。
〔３〕 〔１〕又は〔２〕に記載のアミド化合物と担体とを含有する植物病害防除剤。
〔４〕 〔１〕又は〔２〕に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する植物病害の防除方法。
〔５〕 植物病害を防除するための〔１〕又は〔２〕に記載のアミド化合物の使用。 As a result of studies to find a compound having an excellent control effect against plant diseases, the present inventors have found that the amide compound represented by the following formula (1) has an excellent control effect against plant diseases. The present invention has been reached.
That is, the present invention includes the following [1] to [5].
[1] Formula (1)

[Where,
R ¹ represents a hydrogen atom, a fluorine atom, a C1-C3 alkyl group or a (C1-C3 alkoxy) C1-C3 alkyl group,
R ² represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group, a trifluoromethyl group or a trifluoromethoxy group. ]
An amide compound represented by
[2] R ² is a trifluoromethyl group bonded to the 3-position, a trifluoromethyl group bonded to the 4-position, a trifluoromethoxy group bonded to the 3-position, or a trifluoromethoxy group bonded to the 4-position [1] The amide compound described in 1.
[3] A plant disease control agent comprising the amide compound according to [1] or [2] and a carrier.
[4] A method for controlling plant diseases comprising a step of treating an effective amount of the amide compound according to [1] or [2] to a plant or soil.
[5] Use of the amide compound according to [1] or [2] for controlling plant diseases.

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

In the compound of the present invention,
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the C1-C3 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
Examples of the C1-C3 alkoxy group include a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group.
Examples of (C1-C3 alkoxy) C1-C3 alkyl groups include methoxymethyl group, ethoxymethyl group, 1-methoxyethyl group, 1-ethoxyethyl group, 1-propoxyethyl group, 1-isopropoxyethyl group, 2 -Methoxypropyl group, 2-ethoxypropyl group, 2-propoxypropyl group and 2-isopropoxypropyl group are mentioned.

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 (1);
An amide compound in which R ¹ is a fluorine atom in formula (1);
An amide compound in which R ¹ is a C1-C3 alkyl group in formula (1);
An amide compound represented by formula (1), wherein R ¹ is a (C1-C3 alkoxy) C1-C3 alkyl group;

An amide compound in which R ² is a halogen atom, a trifluoromethyl group or a trifluoromethoxy group in formula (1);

An amide compound in which R ² is a halogen atom, a trifluoromethyl group or a trifluoromethoxy group in the formula (1), and the bonding position of R ² is the 3-position or the 4-position;
An amide compound in which R ² is a trifluoromethyl group or a trifluoromethoxy group and the bonding position of R ² is the 3-position or the 4-position in Formula (1);

An amide compound in which R ¹ is a hydrogen atom and R ² is a halogen atom, a trifluoromethyl group or a trifluoromethoxy group in formula (1);
An amide compound in which R ¹ is a fluorine atom and R ² is a halogen atom, a trifluoromethyl group or a trifluoromethoxy group in formula (1);
An amide compound in which R ¹ is a C1-C3 alkyl group and R ² is a halogen atom, a trifluoromethyl group or a trifluoromethoxy group in formula (1);
An amide compound in which R ¹ is a (C1-C3 alkoxy) C1-C3 alkyl group and R ² is a halogen atom, a trifluoromethyl group or a trifluoromethoxy group in the formula (1);

In Formula (1), R ¹ is a hydrogen atom, R ² is a halogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group, a trifluoromethyl group, or a trifluoromethoxy group, and the bonding position of R ² is An amide compound in the 3rd or 4th position;
In Formula (1), R ¹ is a fluorine atom, R ² is a halogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group, a trifluoromethyl group, or a trifluoromethoxy group, and the bonding position of R ² is An amide compound in the 3rd or 4th position;
In the formula (1), R ¹ is C1-C3 alkyl group, R ² is a halogen atom, C1-C3 alkyl group, C1-C3 alkoxy group, a trifluoromethyl group or a trifluoromethoxy group, a R ² An amide compound in which the bonding position is the 3-position or the 4-position;
In the formula (1), R ¹ is a (C1-C3 alkoxy) C1-C3 alkyl group, and R ² is a halogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group, a trifluoromethyl group or a trifluoromethoxy group. An amide compound in which R ² is bonded at the 3-position or the 4-position;

In formula (1), an amide compound in which R ² is bonded at the 3-position or the 4-position, and R ² is a halogen atom, a trifluoromethyl group or a trifluoromethoxy group;

An amide compound in which R ¹ is a hydrogen atom in formula (1), the bonding position of R ² is the 3- or 4-position, and R ² is a halogen atom;
An amide compound represented by formula (1), wherein R ¹ is a fluorine atom, the bonding position of R ² is the 3- or 4-position, and R ² is a halogen atom;
In formula (1), R ¹ is a C1-C3 alkyl group, the bonding position of R ² is the 3-position or 4-position, and R ² is a halogen atom, and in formula (1), R ¹ is (C1-C3 alkoxy) Amide compound which is a C1-C3 alkyl group, the bonding position of R ² is the 3-position or the 4-position, and R ² is a halogen atom.

  The compound of the present invention can be produced, for example, by the following production method.

〔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と記す場合がある。）、エチレングリコールジメチルエーテル及びターシャリー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、、トルエン及びキシレン等の芳香族炭化水素、クロロベンゼン等のハロゲン化炭化水素、酢酸ブチル及び酢酸エチル等のエステル、アセトニトリル等のニトリル、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、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、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。）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、（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。）等のホスホニウム塩が挙げられる。
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−２０〜１００℃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、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 1)
The compound of the present invention can be produced by reacting compound (2) with compound (3) or a salt thereof (for example, hydrochloride) in the presence of a dehydration condensing agent.

[Wherein, R ¹ and R ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter sometimes referred to as THF), ethylene glycol dimethyl ether and tertiary butyl methyl ether (hereinafter sometimes referred to as MTBE), toluene, and the like. And aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and N, N-dimethylformamide (hereinafter sometimes referred to as DMF). Examples thereof include sulfoxides such as acid amides and dimethyl sulfoxide (hereinafter sometimes referred to as DMSO), nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine, 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, (benzo And phosphonium salts such as triazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (hereinafter referred to as BOP reagent).
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 −20 to 100 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as filtration of the reaction mixture, extraction of the filtrate with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

〔式中、Ｒ¹及びＲ²は前記と同じ意味を表す。〕
（工程２−１）
化合物（４）又はその塩（例えば、塩酸塩が挙げられる。）は、化合物（２）と塩素化剤とを反応させることにより製造することができる。
該反応は、通常溶媒の存在下又は非存在下で行われる。
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及びこれらの混合物が挙げられる。
塩素化剤としては、塩化チオニル、オキシ塩化リン、塩化オキザリル又はホスゲン等が挙げられる。
化合物（２）１モルに対して、塩素化剤が通常1モル〜過剰量の割合で用いられる。
該反応の反応温度は通常室温から１１０℃の範囲であり、反応時間は通常瞬時〜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（４）又はその塩（例えば、塩酸塩が挙げられる。）を単離することができる。
（工程２−２）
本発明化合物は、化合物（４）又はその塩（例えば、塩酸塩が挙げられる。）と、化合物（３）又はその塩（例えば、塩酸塩が挙げられる。）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。
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及びＭＴＢＥ等のエーテル、ヘキサン、へプタン及びオクタンの脂肪族炭化水素、トルエン及びキシレン等の芳香族炭化水素、クロロベンゼン等のハロゲン化炭化水素、酢酸ブチル及び酢酸エチル等のエステル、アセトニトリル等のニトリル、ＤＭＦ等の酸アミド、ＤＭＳＯ等のスルホキシド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、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（４）１モルに対して、化合物（３）が通常１〜３モルの割合、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、濾液に水を加えて有機溶媒で抽出し、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、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 2)
The compound of the present invention can also be produced by the following scheme.

[Wherein, R ¹ and R ² represent the same meaning as described above. ]
(Step 2-1)
Compound (4) or a salt thereof (for example, hydrochloride can be mentioned) can be produced by reacting compound (2) with a chlorinating agent.
The reaction is usually performed in the presence or absence 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 mixtures thereof.
Examples of the chlorinating agent include thionyl chloride, phosphorus oxychloride, oxalyl chloride or phosgene.
The chlorinating agent is usually used in a proportion of 1 mol to excess with respect to 1 mol of the compound (2).
The reaction temperature of the reaction is usually in the range of room temperature to 110 ° C., and the reaction time is usually in the range of instantaneous to 24 hours.
After completion of the reaction, the compound (4) or a salt thereof (for example, hydrochloride) can be isolated by performing a post-treatment operation such as concentrating the reaction mixture.
(Process 2-2)
The compound of the present invention is obtained by reacting compound (4) or a salt thereof (for example, hydrochloride) with compound (3) or a salt thereof (for example, hydrochloride) in the presence of a base. Can be manufactured.
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 halogenated carbonization such as chlorobenzene. Examples include hydrogen, 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. Can be mentioned.
The compound (3) is usually used in a proportion of 1 to 3 mol and the base is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (4).
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 1 to 24 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as filtering the reaction mixture, adding water to the filtrate and extracting with an organic solvent, and drying and concentrating the organic layer. it can. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

Specific examples of the compound of the present invention include the following compounds.
N- (3-phenyloxyphenyl) methyl-nicotinic acid amide,
N- (3-phenyloxyphenyl) methyl-6-fluoronicotinic acid amide,
N- (3-phenyloxyphenyl) methyl-6-methylnicotinic acid amide,
N- (3-phenyloxyphenyl) methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-fluorophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-nicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-propylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-methoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-isopropoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-isopropoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-nicotinic acid amide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-nicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-nicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-Isopropoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6-fluoronicotinic acid amide,
N- [3- (2-fluorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6-methylnicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-isopropylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6-methylnicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-Isopropoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6-ethylnicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6-propylnicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-isopropylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-Isopropoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6-propylnicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-Isopropoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6-isopropylnicotinamide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6-isopropylnicotinamide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6-isopropylnicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-isopropylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-isopropoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6-methoxymethylnicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinamide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinamide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinamide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinamide,
N- [3- (3-isopropylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinamide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinamide,
N- [3- (2-Isopropoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-methoxyethyl) nicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (3-isopropylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (4-Ethoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (2-isopropoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinamide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-ethoxyethyl) nicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-isopropylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (2-Isopropoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-propoxyethyl) nicotinamide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (2-Isopropoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinic acid amide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6- (1-isopropoxyethyl) nicotinamide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (2-isopropoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (3-isopropoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinamide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-methoxypropyl) nicotinic acid amide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-Ethoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-isopropoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinic acid amide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-ethoxypropyl) nicotinamide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-ethoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-isopropoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,
N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-propoxypropyl) nicotinamide,

N- [3- (2-fluorophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-fluorophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (4-fluorophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (2-chlorophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (3-chlorophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (4-chlorophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (2-bromophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (3-bromophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (4-bromophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (2-iodophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-iodophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (4-iodophenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,

N- [3- (2-methylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (3-methylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (4-methylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (2-ethylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (3-ethylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (4-ethylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (2-propylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-propylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (4-propylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (2-isopropylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-Isopropylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (4-Isopropylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,

N- [3- (2-methoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (3-methoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (4-methoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (2-ethoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-ethoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (4-Ethoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (2-propoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-propoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinic acid amide,
N- [3- (4-propoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (2-isopropoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-Isopropoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (4-Isopropoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,

N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (2-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide,
N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6- (2-isopropoxypropyl) nicotinamide and N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6 -(2-Isopropoxypropyl) nicotinamide.

  The present control agent may consist only of the present compound, but usually the present compound is mixed with a solid carrier, liquid carrier, gas carrier, surfactant, etc., and if necessary, a fixing agent, a dispersion Additives for preparations such as powders and stabilizers, wettable powders, granular wettable powders, flowables, granules, dry flowables, emulsions, aqueous liquids, oils, smokes, aerosols, microcapsules It is used in the form of a preparation. These preparations usually contain 0.1 to 99%, preferably 0.2 to 90% by weight of the compound of the present invention.

  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, cyclohexanone, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, , Acetonitrile, isobutylnitrile), ethers (eg , Dioxane, diisopropyl ether), acid amides (e.g., dimethylformamide, 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.

  The method of applying the control agent of the present invention is not particularly limited as long as the control agent of the present invention can be applied substantially, but for example, treatment to plant bodies such as foliage spraying, plant such as soil treatment, etc. And the like, and the treatment of seeds such as seed disinfection.

〔式中、Ｘ¹は水素原子、またはハロゲン原子を表し、Ｘ²はメチル基、ジフルオロメチル基、又はトリフルオロメチル基を表し、Ｑは下記のいずれかの基

を表す。〕
で示されるピラゾールカルボキサミド化合物；

式（１２）

〔式中、Ｘ³はメチル基、ジフルオロメチル基、またはエチル基を表し、Ｘ⁴はメトキシ基、またはメチルアミノ基を表し、Ｘ⁵はフェニル基、２−メチルフェニル基、または２，５−ジメチルフェニル基を表す。〕
で示されるα−アルコキシフェニル酢酸化合物；
式（１３）

〔式中、Ｘ⁶はメトキシ基、エトキシ基、プロポキシ基、２−プロペニルオキシ基、２−プロピニルオキシ基、３−ブテニルオキシ基、３−ブチニルオキシ基、メチルチオ基、エチルチオ基、または２−プロペニルチオ基を表し、Ｘ⁷は１−メチルエチル基、または１−メチルプロピル基を表し、Ｘ⁸は２−メチルフェニル基、または２，６−ジクロロフェニル基を表す。〕
で示されるピラゾリノン化合物、
等があげられる。
かかる他の殺菌剤としては、例えば、プロピコナゾール、プロチオコナゾール、トリアジメノール、プロクロラズ、ペンコナゾール、テブコナゾール、フルシラゾール、ジニコナゾール、ブロムコナゾール、エポキシコナゾール、ジフェノコナゾール、シプロコナゾール、メトコナゾール、トリフルミゾール、テトラコナゾール、マイクロブタニル、フェンブコナゾール、ヘキサコナゾール、フルキンコナゾール、トリティコナゾール、ビテルタノール、イマザリル、フルトリアホール、シメコナゾール、イプコナゾール等のアゾール系殺菌化合物；フェンプロピモルフ、トリデモルフ、フェンプロピジン等の環状アミン系殺菌化合物；カルベンダジム、ベノミル、チアベンダゾール、チオファネートメチル等のベンズイミダゾール系殺菌化合物；プロシミドン；シプロディニル；ピリメタニル；ジエトフェンカルブ；チウラム；フルアジナム；マンコゼブ；イプロジオン；ビンクロゾリン；クロロタロニル；キャプタン；メパニピリム；フェンピクロニル；フルジオキソニル；ジクロフルアニド；フォルペット；クレソキシムメチル；アゾキシストロビン；トリフロキシストロビン；フルオキサストロビン；ピコキシストロビン；ピラクロストロビン；ジモキシストロビン；ピリベンカルブ；メトミノストロビン；エネストロビン；スピロキサミン；キノキシフェン；フェンヘキサミド；ファモキサドン；フェナミドン；ゾキサミド；エタボキサム；アミスルブロム；イプロヴァリカルブ；ベンチアバリカルブ；シアゾファミド；マンジプロパミド；ボスカリド；ペンチオピラド；メトラフェノン；フルオピラン；ビキサフェン；シフルフェナミド；プロキナジド；オリザストロビン；フラメトピル；チフルザミド；メプロニル；フルトラニル；フルスルファミド；フルオピコリド；メタラキシルＭ；キララキシル；フォセチル；シモキサニル；ペンシクロン；トルクロホスメチル；カルプロパミド；ジクロシメット；フェノキサニル；トリシクラゾール；ピロキロン；プロベナゾール；イソチアニル；チアジニル；テブフロキン；ジクロメジン；カスガマイシン；フェリムゾン；フサライド；バリダマイシン；ヒドロキシイソキサゾール；イミノクタジン酢酸塩；イソプロチオラン；オキソリニック酸；オキシテトラサイクリン；ストレプトマイシン；塩基性塩化銅；水酸化第二銅；塩基性硫酸銅；有機銅；硫黄などが挙げられる。 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,
(1) Azole fungicides propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, zebolazole, tebuconazole, tebuconazole diconazole, bromuconazole, epoxyconazole, difenoconazole, cyproconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole. Laconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, triticonazole, triticonazole, triticonazole, triticonazole, triticonazole Flutriafol, simeconazole, ipconazole, etc .;
(2) Amine fungicides fenpropimorph, tridemorph, fenpropidin, spiroxamine, etc .;
(3) benzimidazole fungicides carbendazim, benomyl, thiabendazole, thiophanate-methyl and the like;
(4) Dicarboximide fungicides procymidone, iprodione, vinclozolin and the like;
(5) Anilinopyrimidine fungicides cyprodinil, pyrimethanil, mepanipyrim and the like;
(6) Phenylpyrrole fungicide fenpiclonil, fludioxonil and the like;
(7) The strobilurin fungicide cresoxim-methyl, azoxystrobin, trifloxystrobin, floxastrobin, picoxystrobin (picoxystrobin) pyraclostrobin, dimoxystrobin, pyribencarb, methinostrobin, oryzatrobin, enestrobin, etc .;
(8) Phenylamide fungicide metalaxyl, metalaxyl M or mefenoxam (metalaxyl-M or mefenoxam), benalaxyl, benalaxyl M or kiralaxyl-ra
(9) Carboxylic acid amide fungicides dimethomorph, iprovalicalb, benchavaricarb-isopropyl, mandipropamide, varifenal
(10) Carboxamide fungicides carboxin, mepronil, flutolanil, tifluzamide, furamethpyr, boscalid, pentiopyrofylpentofyfluopent bifafen),
(11) Other fungicides dietophanecarb; thiuram; fluazinam; mancozeb; chlorothalonil; captan; diclofluranide; folpette; quinoxyphene; Flupicolide; fluorpicolide; focetyl; simoxanyl; pencyclon; tolcrofosmethyl; carpropamide; diclocimet; phenoxanyl; tricyclazole; pyroxilone; probenazole; Isoproti Run; oxolinic acid; oxytetracycline; streptomycin; basic copper chloride; cupric hydroxide; basic copper sulfate; organic copper; sulfur and the like;

Formula (11)

[Wherein, X ¹ represents a hydrogen atom or a halogen atom, X ² represents a methyl group, a difluoromethyl group, or a trifluoromethyl group, and Q represents any of the following groups:

Represents. ]
A pyrazole carboxamide compound represented by:

Formula (12)

[Wherein X ³ represents a methyl group, a difluoromethyl group or an ethyl group, X ⁴ represents a methoxy group or a methylamino group, X ⁵ represents a phenyl group, a 2-methylphenyl group, or 2,5- Represents a dimethylphenyl group. ]
An α-alkoxyphenylacetic acid compound represented by:
Formula (13)

[Wherein, X ⁶ is a methoxy group, an ethoxy group, a propoxy group, a 2-propenyloxy group, a 2-propynyloxy group, a 3-butenyloxy group, a 3-butynyloxy group, a methylthio group, an ethylthio group, or a 2-propenylthio group. X ⁷ represents a 1-methylethyl group or a 1-methylpropyl group, and X ⁸ represents a 2-methylphenyl group or a 2,6-dichlorophenyl group. ]
A pyrazolinone compound represented by:
Etc.
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; quinoxyphene; fenhexamide; famoxadone; Avaricarb; Siazofamide; Mandipropamide; Boscalid; Penthiopyrad Metrafenone; fluopyran; bixafen; cyflufenamide; proquinazide; orizastrobin; furametopyr; tifluzamide; mepronil; flutolanil; flusulfamide; Probenazole; Isothianyl; Thiazinyl; Tebufloquine; Diclomedin; Kasugamycin; Ferimzone; Fusaride; Validamycin; Hydroxyisoxazole; Iminoctazine acetate; Isoprothiolane; Oxolinic acid; 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, 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 application amount of the present control agent varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc., but per 10 ares in terms of the amount of the present compound in the present control agent, Usually 1 to 500 g, preferably 2 to 200 g. 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 seed treatment, 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 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. Examples of “crop” to which tolerance has been imparted by genetic engineering techniques include glyphosate and glufosinate-resistant corn varieties such as RoundupReady (registered trademark), RoundupReady2 (registered trademark), and LibertyLink (registered trademark). Already sold by name.

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.

In addition, 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.

In addition, the above-mentioned “crop” is a line to which two or more traits related to herbicide resistance, pest resistance, disease resistance, etc., as described above, are imparted using classical breeding technology or genetic recombination technology, Also included are strains to which two or more properties of the parent strain are imparted by crossing genetically modified plants having similar or different properties.

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), red snow rot (Micronectriella nivale), snow mold Nuclear disease (Typhula sp.), Bare-headed blight (Ustilago tritici), Namahusa smut (Tilletia caries), Eye-printed disease (Pseudocercosporella herpotrichoides), Leaf blight (Mycosphaerella graminicola), Blight (Stagonospora nodorum), Yellow spot (Pyrenophora tritici-repentis), barley powdery mildew (Erysiphe graminis), red mold (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei) ),naked Blackhead disease (Ustilago nuda), cloud disease (Rhynchosporium secalis), reticular disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy leaf disease (Pyrenophora graminea), Rhizoctonia genus Rhizoctonia solani; 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 Scarlet (Ustilago tritici, U. nuda), Namahusa scab (Tilletia caries), Eye spot (Pseudocercosporella herpotrichoides), Cloud disease (Rhynchosporium secalis), Leaf blight ( Septoria tritici), dry blight (Leptosphaeria nodorum), net blotch (Pyrenophora teres Drechsler), blight (Gaeumannomyces graminis), yellow spot (Pyrenophora tritici-repentis); citrus black spot (Diaporthe citri), scab (Elsinoe fawcet ti), fruit rot (Penicillium digitatum, P. italicum); apple monilia (Monilinia mali), rot (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf (Alternaria alternata apple pathotype), black star Disease (Venturia inaequalis), anthracnose (Glomerella cingulata); pear black spot disease (Venturia nashicola, V. pirina), black spot disease (Alternaria alternata Japanese pear pathotype), red star disease (Gymnosporangium haraeanum); (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp. (Phomopsis sp.); Grape black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust ( Phakopsora ampelopsidis), Blacklot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kaki), deciduous disease (Cercospora kaki, Mycosphaerella nawae); Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella melonis), vine split (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.) Blight (Pythium sp.); Tomato ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans); eggplant brown rot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); Brassicaceae vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora parasitica), downy mildew (Peronospora parasitica); green onion rust (Puccinia allii), soybean purple spot (Cercospora) kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), bean anthracnose (Colletotrichum lindemthianum), groundnut black rot (Cercospora pers) onata), brown spot disease (Cercospora arachidicola), white silk disease (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 blast (Exobasidium reticulatum); White scab (Elsinoe leucospila), Ring spot disease (Pestalotiopsis sp.), Anthrax Disease (Colletotrichum theae-sinensis) Tobacco Alternaria longipes, powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae); Disease (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces sochlioides); rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa) Chrysanthemum brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana); onion white spot (Botrytis cinerea, B. byssoidea, B. squamosa), gray rot (Botrytis alli); Botrytis squamosa, various crops of gray mold (Botrytis cinerea), mycorrhizal disease (Sclerotinia sclerotiorum); radish black spot (Alternaria brassicicola); buckwheat dollar spot disease (Sclerotinia homeocarpa); Patch disease and large patch disease (Rhizoctonia solani); and banana sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).

  Next, the present invention will be described more specifically with reference to Examples such as Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited to these examples.

¹H-NMR (CDCl₃)δ: 2.61 (3H, s), 3.81 (3H, s), 4.61 (2H, d, J = 5.6 Hz), 6.37 (1H, br s), 6.84-7.06 (7H, m), 7.23-7.31 (2H, m), 8.00 (1H, dd, J = 8.2, 2.3 Hz), 8.84-8.87 (1H, m). Production Example 1
To a mixture of 0.14 g of 6-methylnicotinic acid, 0.23 g of 3- (4-methoxyphenyloxy) benzylamine and 2 ml of dimethylformamide, 0.51 g of BOP reagent and 0.12 g of triethylamine were sequentially added, followed by stirring at room temperature for 20 hours. did. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.26 g of N- [3- (4-methoxyphenyloxy) methyl] -6-methylnicotinic acid amide (hereinafter referred to as the present compound 1). It was.
Compound 1 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 2.61 (3H, s), 3.81 (3H, s), 4.61 (2H, d, J = 5.6 Hz), 6.37 (1H, br s), 6.84-7.06 (7H, m), 7.23-7.31 (2H, m), 8.00 (1H, dd, J = 8.2, 2.3 Hz), 8.84-8.87 (1H, m).

¹H-NMR (DMSO-D₆) δ: 2.49 (3H, s), 4.43 (2H, d, J = 6.0 Hz), 6.80 (1H, d, J = 8.2 Hz), 6.90 (1H, s), 7.05 (1H, d, J = 7.2 Hz), 7.11-7.23 (3H, m), 7.27-7.38 (3H, m), 8.05 (1H, dd, J = 8.1, 1.6 Hz), 8.86 (1H, d, J = 2.2 Hz), 9.12 (1H, t, J = 5.7 Hz). Production Example 2
To a mixture of 0.20 g of 6-methylnicotinic acid, 0.37 g of 3- (2-fluorophenyloxy) benzylamine hydrochloride and 5 ml of DMF, 0.44 g of triethylamine is added, and then 0.71 g of BOP reagent is added. Stir for hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.27 g of N- [3- (2-fluorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide (hereinafter referred to as the present compound 2). Got.
Compound 2 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.49 (3H, s), 4.43 (2H, d, J = 6.0 Hz), 6.80 (1H, d, J = 8.2 Hz), 6.90 (1H, s), 7.05 (1H, d, J = 7.2 Hz), 7.11-7.23 (3H, m), 7.27-7.38 (3H, m), 8.05 (1H, dd, J = 8.1, 1.6 Hz), 8.86 (1H, d, J = 2.2 Hz), 9.12 (1H, t, J = 5.7 Hz).

¹H-NMR (DMSO-D₆) δ: 2.51 (3H, s), 4.47 (2H, d, J = 5.8 Hz), 6.79-6.86 (2H, m), 6.92-6.98 (2H, m), 7.02 (1H, s), 7.14 (1H, d, J = 8.0 Hz), 7.33-7.42 (3H, m), 8.08 (1H, dd, J = 8.1, 2.1 Hz), 8.89 (1H, d, J = 2.4 Hz), 9.15 (1H, t, J = 5.9 Hz). Production Example 3
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.37 g of 3- (3-fluorophenyloxy) benzylamine hydrochloride and 5 ml of DMF, 0.44 g of triethylamine is added, and then 0.71 g of BOP reagent is added. Stir for hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.19 g of N- [3- (3-fluorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide (hereinafter referred to as the present compound 3). Got.
Compound 3 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.51 (3H, s), 4.47 (2H, d, J = 5.8 Hz), 6.79-6.86 (2H, m), 6.92-6.98 (2H, m), 7.02 (1H, s), 7.14 (1H, d, J = 8.0 Hz), 7.33-7.42 (3H, m), 8.08 (1H, dd, J = 8.1, 2.1 Hz), 8.89 (1H, d, J = 2.4 Hz), 9.15 (1H, t, J = 5.9 Hz).

¹H-NMR (DMSO-D₆) δ: 2.49 (3H, s), 4.43 (2H, d, J = 5.9 Hz), 6.82 (1H, d, J = 7.8 Hz), 6.91 (1H, s), 7.01-7.06 (3H, m), 7.16-7.22 (2H, m), 7.28-7.35 (2H, m), 8.06 (1H, dd, J = 8.0, 2.0 Hz), 8.87 (1H, s), 9.12 (1H, t, J = 5.6 Hz). Production Example 4
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.37 g of 3- (4-fluorophenyloxy) benzylamine hydrochloride and 5 ml of DMF, 0.44 g of triethylamine is added, and then 0.71 g of BOP reagent is added. Stir for hours. Water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous solution of sodium bicarbonate, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (4-fluorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide. (Hereinafter referred to as the present compound 4) 0.39 g was obtained.
Compound 4 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.49 (3H, s), 4.43 (2H, d, J = 5.9 Hz), 6.82 (1H, d, J = 7.8 Hz), 6.91 (1H, s), 7.01-7.06 (3H, m), 7.16-7.22 (2H, m), 7.28-7.35 (2H, m), 8.06 (1H, dd, J = 8.0, 2.0 Hz), 8.87 (1H, s), 9.12 ( (1H, t, J = 5.6 Hz).

¹H-NMR (DMSO-D₆) δ: 2.51 (3H, s), 4.45 (2H, d, J = 5.8 Hz), 6.79 (1H, d, J = 8.0 Hz), 6.91 (1H, s), 7.06-7.10 (2H, m), 7.20-7.21 (1H, m), 7.30-7.38 (3H, m), 7.58 (1H, dd, J = 8.0, 1.4 Hz), 8.07 (1H, d, J = 8.9 Hz), 8.88 (1H, s), 9.14 (1H, t, J = 5.4 Hz). Production Example 5
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.34 g of 3- (2-chlorophenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine was added, and then 0.71 g of BOP reagent was added, followed by stirring at room temperature for 3 hours. . Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 0.32 g of N- [3- (2-chlorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide (hereinafter referred to as the present compound 5). Obtained.
Compound 5 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.51 (3H, s), 4.45 (2H, d, J = 5.8 Hz), 6.79 (1H, d, J = 8.0 Hz), 6.91 (1H, s), 7.06-7.10 (2H, m), 7.20-7.21 (1H, m), 7.30-7.38 (3H, m), 7.58 (1H, dd, J = 8.0, 1.4 Hz), 8.07 (1H, d, J = 8.9 Hz), 8.88 (1H, s), 9.14 (1H, t, J = 5.4 Hz).

¹H-NMR (DMSO-D₆) δ: 2.51 (3H, s), 4.47 (2H, d, J = 5.8 Hz), 6.93-6.96 (2H, m), 7.00-7.03 (2H, m), 7.13-7.19 (2H, m), 7.33-7.41 (3H, m), 8.08 (1H, d, J = 8.0 Hz), 8.89 (1H, s), 9.15 (1H, t, J = 5.6 Hz). Production Example 6
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.34 g of 3- (3-chlorophenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine was added, and then 0.71 g of BOP reagent was added, followed by stirring at room temperature for 3 hours. . Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. Ethyl acetate and MTBE were added to the resulting residue, and the resulting solid was collected by filtration to give N- [3- (3-chlorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide (hereinafter referred to as the present compound 6). .) 0.13 g was obtained.
Compound 6 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.51 (3H, s), 4.47 (2H, d, J = 5.8 Hz), 6.93-6.96 (2H, m), 7.00-7.03 (2H, m), 7.13 -7.19 (2H, m), 7.33-7.41 (3H, m), 8.08 (1H, d, J = 8.0 Hz), 8.89 (1H, s), 9.15 (1H, t, J = 5.6 Hz).

¹H-NMR (DMSO-D₆) δ: 2.49 (3H, s), 4.45 (2H, d, J = 6.0 Hz), 6.88 (1H, d, J = 8.0 Hz), 6.95-7.01 (3H, m), 7.10 (1H, d, J = 7.7 Hz), 7.31-7.40 (4H, m), 8.06 (1H, dd, J = 8.0, 2.2 Hz), 8.88 (1H, s), 9.13 (1H, t, J = 5.9 Hz). Production Example 7
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.34 g of 3- (4-chlorophenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine was added, and then 0.71 g of BOP reagent was added, followed by stirring at room temperature for 3 hours. . Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous solution of sodium hydrogen carbonate, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (4-chlorophenyloxy) phenyl] methyl-6-methylnicotinic acid amide ( Hereinafter referred to as the present compound 7.) 0.39 g was obtained.
Compound 7 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.49 (3H, s), 4.45 (2H, d, J = 6.0 Hz), 6.88 (1H, d, J = 8.0 Hz), 6.95-7.01 (3H, m ), 7.10 (1H, d, J = 7.7 Hz), 7.31-7.40 (4H, m), 8.06 (1H, dd, J = 8.0, 2.2 Hz), 8.88 (1H, s), 9.13 (1H, t, J = 5.9 Hz).

¹H-NMR (DMSO-D₆) δ: 2.14 (3H, s), 2.51 (3H, s), 4.43 (2H, d, J = 6.1 Hz), 6.72 (1H, dd, J = 8.3, 1.7 Hz), 6.83-6.89 (2H, m), 7.02 (1H, d, J = 7.8 Hz), 7.08 (1H, dd, J = 7.4, 6.2 Hz), 7.16-7.21 (1H, m), 7.26-7.31 (2H, m), 7.35 (1H, d, J = 8.0 Hz), 8.06 (1H, dd, J = 8.0, 2.4 Hz), 8.87 (1H, d, J = 1.7 Hz), 9.12 (1H, t, J = 6.0 Hz). Production Example 8
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.31 g of 3- (2-methylphenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine was added, and then 0.71 g of BOP reagent was added, followed by stirring at room temperature for 3 hours. did. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.28 g of N- [3- (2-methylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide (hereinafter referred to as the present compound 8). Got.
Compound 8 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.14 (3H, s), 2.51 (3H, s), 4.43 (2H, d, J = 6.1 Hz), 6.72 (1H, dd, J = 8.3, 1.7 Hz ), 6.83-6.89 (2H, m), 7.02 (1H, d, J = 7.8 Hz), 7.08 (1H, dd, J = 7.4, 6.2 Hz), 7.16-7.21 (1H, m), 7.26-7.31 ( 2H, m), 7.35 (1H, d, J = 8.0 Hz), 8.06 (1H, dd, J = 8.0, 2.4 Hz), 8.87 (1H, d, J = 1.7 Hz), 9.12 (1H, t, J = 6.0 Hz).

¹H-NMR (DMSO-D₆) δ: 2.23 (3H, s), 2.49 (3H, s), 4.44 (2H, d, J = 5.9 Hz), 6.76 (1H, d, J = 8.3 Hz), 6.79 (1H, s), 6.83 (1H, d, J = 7.8 Hz), 6.90-6.94 (2H, m), 7.06 (1H, d, J = 7.3 Hz), 7.22 (1H, t, J = 7.8 Hz), 7.28-7.37 (2H, m), 8.06 (1H, dd, J = 8.0, 2.0 Hz), 8.87 (1H, s), 9.12 (1H, t, J = 5.6 Hz). Production Example 9
Add 0.44 g of triethylamine to a mixture of 0.20 g of 6-methylnicotinic acid, 0.31 g of 3- (3-methylphenyloxy) benzylamine and 5 ml of DMF, then add 0.71 g of BOP reagent, and stir at room temperature for 3 hours. did. Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous sodium hydrogen carbonate solution, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (3-methylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide. (Hereinafter referred to as the present compound 9) 0.35 g was obtained.
Compound 9 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.23 (3H, s), 2.49 (3H, s), 4.44 (2H, d, J = 5.9 Hz), 6.76 (1H, d, J = 8.3 Hz), 6.79 (1H, s), 6.83 (1H, d, J = 7.8 Hz), 6.90-6.94 (2H, m), 7.06 (1H, d, J = 7.3 Hz), 7.22 (1H, t, J = 7.8 Hz ), 7.28-7.37 (2H, m), 8.06 (1H, dd, J = 8.0, 2.0 Hz), 8.87 (1H, s), 9.12 (1H, t, J = 5.6 Hz).

¹H-NMR (DMSO-D₆) δ: 2.25 (3H, s), 2.49 (3H, s), 4.42 (2H, d, J = 6.1 Hz), 6.80 (1H, dd, J = 8.0, 2.2 Hz), 6.86-6.89 (3H, m), 7.03 (1H, d, J = 7.6 Hz), 7.13-7.16 (2H, m), 7.26-7.30 (1H, m), 7.33 (1H, d, J = 8.0 Hz), 8.05 (1H, dd, J = 8.0, 2.2 Hz), 8.86 (1H, d, J = 2.0 Hz), 9.11 (1H, t, J = 5.9 Hz). Production Example 10
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.31 g of 3- (4-methylphenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine was added, and then 0.71 g of BOP reagent was added, followed by stirring at room temperature for 3 hours. did. Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous solution of sodium bicarbonate, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (4-methylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide. (Hereafter, it describes as this invention compound 10.) 0.38g was obtained.
Compound 10 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.25 (3H, s), 2.49 (3H, s), 4.42 (2H, d, J = 6.1 Hz), 6.80 (1H, dd, J = 8.0, 2.2 Hz ), 6.86-6.89 (3H, m), 7.03 (1H, d, J = 7.6 Hz), 7.13-7.16 (2H, m), 7.26-7.30 (1H, m), 7.33 (1H, d, J = 8.0 Hz), 8.05 (1H, dd, J = 8.0, 2.2 Hz), 8.86 (1H, d, J = 2.0 Hz), 9.11 (1H, t, J = 5.9 Hz).

¹H-NMR (DMSO-D₆) δ: 2.52 (3H, s), 4.50 (2H, d, J = 6.0 Hz), 6.92 (1H, dd, J = 8.0, 2.4 Hz), 7.01-7.05 (2H, m), 7.17 (1H, d, J = 7.7 Hz), 7.29-7.41 (3H, m), 7.62-7.67 (1H, m), 7.78 (1H, d, J = 7.0 Hz), 8.09 (1H, dd, J = 8.1, 2.3 Hz), 8.91 (1H, d, J = 2.2 Hz), 9.17 (1H, t, J = 5.9 Hz). Production Example 11
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.39 g of 3- (2-trifluoromethylphenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine is added, and then 0.71 g of BOP reagent is added. Stir for hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and N- [3- (2-trifluoromethylphenyloxy) phenyl] methyl-6-methylnicotinic acid amide (hereinafter referred to as the present compound 11) 0 .35 g was obtained.
Compound 11 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.52 (3H, s), 4.50 (2H, d, J = 6.0 Hz), 6.92 (1H, dd, J = 8.0, 2.4 Hz), 7.01-7.05 (2H , m), 7.17 (1H, d, J = 7.7 Hz), 7.29-7.41 (3H, m), 7.62-7.67 (1H, m), 7.78 (1H, d, J = 7.0 Hz), 8.09 (1H, dd, J = 8.1, 2.3 Hz), 8.91 (1H, d, J = 2.2 Hz), 9.17 (1H, t, J = 5.9 Hz).

¹H-NMR (DMSO-D₆) δ: 2.52 (3H, s), 4.49 (2H, d, J = 5.9 Hz), 6.98 (1H, d, J = 8.0 Hz), 7.05 (1H, s), 7.18 (1H, d, J = 7.6 Hz), 7.27-7.31 (2H, m), 7.35 (1H, d, J = 8.3 Hz), 7.38-7.43 (1H, m), 7.48 (1H, d, J = 7.8 Hz), 7.59-7.64 (1H, m), 8.09 (1H, dd, J = 8.0, 2.4 Hz), 8.90 (1H, d, J = 2.0 Hz), 9.16 (1H, t, J = 5.7 Hz). Production Example 12
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.39 g of 3- (3-trifluoromethylphenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine is added, and then 0.71 g of BOP reagent is added. Stir for hours. Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous solution of sodium bicarbonate, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (3-trifluoromethylphenyloxy) phenyl] methyl-6-methylnicotine. 0.43 g of acid amide (hereinafter referred to as the present compound 12) was obtained.
Compound 12 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.52 (3H, s), 4.49 (2H, d, J = 5.9 Hz), 6.98 (1H, d, J = 8.0 Hz), 7.05 (1H, s), 7.18 (1H, d, J = 7.6 Hz), 7.27-7.31 (2H, m), 7.35 (1H, d, J = 8.3 Hz), 7.38-7.43 (1H, m), 7.48 (1H, d, J = 7.8 Hz), 7.59-7.64 (1H, m), 8.09 (1H, dd, J = 8.0, 2.4 Hz), 8.90 (1H, d, J = 2.0 Hz), 9.16 (1H, t, J = 5.7 Hz) .

¹H-NMR (DMSO-D₆) δ: 2.52 (3H, s), 4.50 (2H, d, J = 5.9 Hz), 7.02 (1H, d, J = 8.0 Hz), 7.08 (1H, s), 7.13 (2H, d, J = 8.8 Hz), 7.21 (1H, d, J = 7.6 Hz), 7.36 (1H, d, J = 8.0 Hz), 7.40-7.44 (1H, m), 7.73 (2H, d, J = 8.8 Hz), 8.10 (1H, dd, J = 8.0, 2.2 Hz), 8.91 (1H, d, J = 2.2 Hz), 9.17 (1H, t, J = 5.9 Hz). Production Example 13
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.39 g of 3- (4-trifluoromethylphenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine is added, and then 0.71 g of BOP reagent is added. Stir for hours. Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous sodium hydrogen carbonate solution, water and a mixed solvent of MTBE and hexane, and dried to give N- [3- (4-trifluoromethylphenyloxy) phenyl] methyl-6-methylnicotine. 0.47 g of acid amide (hereinafter referred to as the present compound 13) was obtained.
Compound 13 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.52 (3H, s), 4.50 (2H, d, J = 5.9 Hz), 7.02 (1H, d, J = 8.0 Hz), 7.08 (1H, s), 7.13 (2H, d, J = 8.8 Hz), 7.21 (1H, d, J = 7.6 Hz), 7.36 (1H, d, J = 8.0 Hz), 7.40-7.44 (1H, m), 7.73 (2H, d , J = 8.8 Hz), 8.10 (1H, dd, J = 8.0, 2.2 Hz), 8.91 (1H, d, J = 2.2 Hz), 9.17 (1H, t, J = 5.9 Hz).

¹H-NMR (DMSO-D₆) δ: 2.52 (3H, s), 3.70 (3H, s), 4.43 (2H, d, J = 5.8 Hz), 6.66 (1H, dd, J = 8.2, 2.4 Hz), 6.81 (1H, s), 6.93-7.03 (3H, m), 7.14-7.27 (3H, m), 7.36 (1H, d, J = 8.0 Hz), 8.07 (1H, dd, J = 8.0, 2.2 Hz), 8.89 (1H, d, J = 2.2 Hz), 9.13 (1H, t, J = 5.9 Hz). Production Example 14
Add 0.44 g of triethylamine to a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.34 g of 3- (2-methoxyphenyloxy) benzylamine and 5 ml of DMF, then add 0.71 g of BOP reagent, and stir at room temperature for 3 hours. did. Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous solution of sodium bicarbonate, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (2-methoxyphenyloxy) phenyl] methyl-6-methylnicotinic acid amide. (Hereinafter referred to as the present compound 14) 0.45 g was obtained.
Compound 14 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.52 (3H, s), 3.70 (3H, s), 4.43 (2H, d, J = 5.8 Hz), 6.66 (1H, dd, J = 8.2, 2.4 Hz ), 6.81 (1H, s), 6.93-7.03 (3H, m), 7.14-7.27 (3H, m), 7.36 (1H, d, J = 8.0 Hz), 8.07 (1H, dd, J = 8.0, 2.2 Hz), 8.89 (1H, d, J = 2.2 Hz), 9.13 (1H, t, J = 5.9 Hz).

¹H-NMR (DMSO-D₆) δ: 2.52 (3H, s), 3.71 (3H, s), 4.47 (2H, d, J = 6.0 Hz), 6.52-6.57 (2H, m), 6.71 (1H, dd, J = 8.2, 2.2 Hz), 6.90 (1H, d, J = 8.0 Hz), 6.98 (1H, s), 7.10 (1H, d, J = 7.7 Hz), 7.24-7.29 (1H, m), 7.32-7.37 (2H, m), 8.09 (1H, dd, J = 8.0, 2.2 Hz), 8.90 (1H, d, J = 2.2 Hz), 9.16 (1H, t, J = 5.7 Hz). Production Example 15
Add 0.44 g of triethylamine to a mixture of 0.20 g of 6-methylnicotinic acid, 0.34 g of 3- (3-methoxyphenyloxy) benzylamine and 5 ml of DMF, then add 0.71 g of BOP reagent, and stir at room temperature for 3 hours. did. Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous solution of sodium bicarbonate, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (3-methoxyphenyloxy) phenyl] methyl-6-methylnicotinic acid amide. (Hereinafter referred to as the present compound 15) 0.28 g was obtained.
Compound 15 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.52 (3H, s), 3.71 (3H, s), 4.47 (2H, d, J = 6.0 Hz), 6.52-6.57 (2H, m), 6.71 (1H , dd, J = 8.2, 2.2 Hz), 6.90 (1H, d, J = 8.0 Hz), 6.98 (1H, s), 7.10 (1H, d, J = 7.7 Hz), 7.24-7.29 (1H, m) , 7.32-7.37 (2H, m), 8.09 (1H, dd, J = 8.0, 2.2 Hz), 8.90 (1H, d, J = 2.2 Hz), 9.16 (1H, t, J = 5.7 Hz).

¹H-NMR (DMSO-D₆) δ: 2.52 (3H, s), 4.50 (2H, d, J = 5.8 Hz), 6.95-7.02 (3H, m), 7.05 (1H, s), 7.12 (1H, d, J = 8.0 Hz), 7.18 (1H, d, J = 7.7 Hz), 7.35-7.42 (2H, m), 7.50 (1H, t, J = 8.3 Hz), 8.10 (1H, dd, J = 8.0, 2.1 Hz), 8.91 (1H, d, J = 2.1 Hz), 9.16 (1H, t, J = 5.3 Hz). Production Example 16
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.41 g of 3- (3-trifluoromethoxyphenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine is added, and then 0.71 g of BOP reagent is added. Stir for hours. Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed sequentially with a saturated aqueous solution of sodium bicarbonate, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (3-trifluoromethoxyphenyloxy) phenyl] methyl-6-methylnicotine. 0.40 g of acid amide (hereinafter referred to as the present compound 16) was obtained.
Compound 16 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.52 (3H, s), 4.50 (2H, d, J = 5.8 Hz), 6.95-7.02 (3H, m), 7.05 (1H, s), 7.12 (1H , d, J = 8.0 Hz), 7.18 (1H, d, J = 7.7 Hz), 7.35-7.42 (2H, m), 7.50 (1H, t, J = 8.3 Hz), 8.10 (1H, dd, J = 8.0, 2.1 Hz), 8.91 (1H, d, J = 2.1 Hz), 9.16 (1H, t, J = 5.3 Hz).

¹H-NMR (DMSO-D₆) δ: 2.52 (3H, s), 4.49 (2H, d, J = 5.8 Hz), 6.94 (1H, d, J = 8.0 Hz), 7.02 (1H, s), 7.10 (2H, d, J = 8.9 Hz), 7.15 (1H, d, J = 7.7 Hz), 7.35-7.40 (4H, m), 8.10 (1H, dd, J = 8.0, 1.7 Hz), 8.91 (1H, s), 9.16 (1H, t, J = 5.7 Hz). Production Example 17
To a mixed solution of 0.20 g of 6-methylnicotinic acid, 0.41 g of 3- (4-trifluoromethoxyphenyloxy) benzylamine and 5 ml of DMF, 0.44 g of triethylamine is added, and then 0.71 g of BOP reagent is added. Stir for hours. Ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous solution of sodium bicarbonate, water and a mixed solvent of MTBE and hexane, and then dried to give N- [3- (4-trifluoromethoxyphenyloxy) phenyl] methyl-6-methylnicotine. 0.37 g of acid amide (hereinafter referred to as the present compound 17) was obtained.
Compound 17 of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.52 (3H, s), 4.49 (2H, d, J = 5.8 Hz), 6.94 (1H, d, J = 8.0 Hz), 7.02 (1H, s), 7.10 (2H, d, J = 8.9 Hz), 7.15 (1H, d, J = 7.7 Hz), 7.35-7.40 (4H, m), 8.10 (1H, dd, J = 8.0, 1.7 Hz), 8.91 (1H , s), 9.16 (1H, t, J = 5.7 Hz).

¹H-NMR (CDCl₃) δ: 4.63 (2H, d, J = 5.8 Hz), 6.68 (1H, br s), 6.91-6.95 (1H, m), 7.00-7.01 (3H, m), 7.08-7.14 (2H, m), 7.29-7.43 (4H, m), 8.14 (1H, dt, J = 8.0, 1.8 Hz), 8.71 (1H, dd, J = 4.8, 1.4 Hz), 8.97 (1H, d, J = 2.2 Hz). Production Example 18
1.0 g of triethylamine was added to a mixture of 0.25 g of nicotinic acid chloride hydrochloride, 0.30 g of 3-phenoxybenzylamine hydrochloride and 4 ml of THF, and the mixture was stirred at room temperature for 3 hours. Thereafter, ice water was added to the reaction mixture, and the resulting solid was collected by filtration. The obtained solid was washed successively with a saturated aqueous solution of sodium hydrogen carbonate, water and a mixed solvent of MTBE and hexane, dried, and then N- (3-phenoxyphenyl) methyl-nicotinic acid amide (hereinafter referred to as the present compound 18). .) 0.54 g was obtained.
Compound 18 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 4.63 (2H, d, J = 5.8 Hz), 6.68 (1H, br s), 6.91-6.95 (1H, m), 7.00-7.01 (3H, m), 7.08- 7.14 (2H, m), 7.29-7.43 (4H, m), 8.14 (1H, dt, J = 8.0, 1.8 Hz), 8.71 (1H, dd, J = 4.8, 1.4 Hz), 8.97 (1H, d, J = 2.2 Hz).

¹H-NMR (CDCl₃) δ: 2.61 (3H, s), 4.63 (2H, d, J = 5.6 Hz), 6.50 (1H, br s), 6.92 (1H, dd, J = 8.0, 2.2 Hz), 6.98-7.02 (3H, m), 7.08-7.13 (2H, m), 7.22-7.36 (4H, m), 8.01 (1H, dd, J = 8.0, 2.2 Hz), 8.86 (1H, d, J = 2.2 Hz). Production Example 19
To a mixture of 0.14 g of 6-methylnicotinic acid, 0.20 g of 3-phenoxybenzylamine and 2 ml of dimethylformamide, 0.51 g of BOP reagent and 0.12 g of triethylamine were sequentially added and stirred at room temperature for 20 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.16 g of N- (3-phenoxyphenyl) methyl-6-methyl-nicotinic acid amide (hereinafter referred to as the present compound 19).
Compound 19 of the present invention

¹ H-NMR (CDCl ₃ ) δ: 2.61 (3H, s), 4.63 (2H, d, J = 5.6 Hz), 6.50 (1H, br s), 6.92 (1H, dd, J = 8.0, 2.2 Hz) , 6.98-7.02 (3H, m), 7.08-7.13 (2H, m), 7.22-7.36 (4H, m), 8.01 (1H, dd, J = 8.0, 2.2 Hz), 8.86 (1H, d, J = 2.2 Hz).

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

¹H-NMR (DMSO-D₆) δ: 4.00 (2H, s), 6.97-7.05 (3H, m), 7.14-7.19 (1H, m), 7.22-7.25 (1H, m), 7.28-7.31 (1H, m), 7.38-7.44 (3H, m), 8.59 (3H, br s). Reference production example 1
A mixture of 35.0 g of 3-phenoxybenzaldehyde, 18.5 g of hydroxylamine hydrochloride, 200 ml of ethanol and 18.2 g of water was stirred at room temperature for 2 hours and then left overnight. To the reaction mixture were added 10 mol / L-hydrochloric acid (18 ml) and 10% palladium carbon (2.5 g), and the mixture was stirred for 6 hours under a normal pressure hydrogen atmosphere. The reaction mixture was filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. The obtained residue was washed with water to obtain 33.5 g of 3-phenoxybenzylamine hydrochloride.
3-phenoxybenzylamine hydrochloride

¹ H-NMR (DMSO-D ₆ ) δ: 4.00 (2H, s), 6.97-7.05 (3H, m), 7.14-7.19 (1H, m), 7.22-7.25 (1H, m), 7.28-7.31 ( 1H, m), 7.38-7.44 (3H, m), 8.59 (3H, br s).

¹H-NMR (CDCl₃) δ: 2.36 (3H, s), 6.81-6.86 (2H, m), 7.00-7.03 (1H, m), 7.18-7.49 (5H, m).
水素化リチウムアルミニウム１．８ｇ及びＴＨＦ５０ｍｌの混合溶液に、３−（３−メチルフェニルオキシ）ベンゾニトリル８．１ｇを０℃で滴下した後、室温で３時間攪拌した。反応混合物に水、１５％水酸化ナトリウム水溶液及び水を順次加え、室温で４時間攪拌した。反応混合物をセライト（登録商標）でろ過し、ろ液を減圧下濃縮した。得られた残渣にＭＴＢＥ及び炭酸カリウムを加え、セライト（登録商標）でろ過し、ろ液を減圧下濃縮し、３−（３−メチルフェニルオキシ）ベンジルアミン７．５ｇを得た。
３−（３−メチルフェニルオキシ）ベンジルアミン

¹H-NMR (CDCl₃) δ: 1.44 (2H, br s), 2.32 (3H, s), 3.84 (2H, s), 6.79-6.96 (5H, m), 7.01-7.06 (1H, m), 7.19-7.30 (2H, m). Reference production example 2
A mixture of 6.0 g of 3-fluorobenzonitrile, 6.0 g of 3-methylphenol, 17 g of cesium carbonate and 50 ml of DMF was heated to reflux for 2 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, 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 obtained residue was subjected to silica gel column chromatography to obtain 8.1 g of 3- (3-methylphenyloxy) benzonitrile.
3- (3-Methylphenyloxy) benzonitrile

¹ H-NMR (CDCl ₃ ) δ: 2.36 (3H, s), 6.81-6.86 (2H, m), 7.00-7.03 (1H, m), 7.18-7.49 (5H, m).
To a mixed solution of 1.8 g of lithium aluminum hydride and 50 ml of THF, 8.1 g of 3- (3-methylphenyloxy) benzonitrile was added dropwise at 0 ° C., followed by stirring at room temperature for 3 hours. Water, a 15% aqueous sodium hydroxide solution and water were sequentially added to the reaction mixture, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. MTBE and potassium carbonate were added to the resulting residue, filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure to obtain 7.5 g of 3- (3-methylphenyloxy) benzylamine.
3- (3-Methylphenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.44 (2H, br s), 2.32 (3H, s), 3.84 (2H, s), 6.79-6.96 (5H, m), 7.01-7.06 (1H, m), 7.19-7.30 (2H, m).

¹H-NMR (CDCl₃) δ: 1.40 (2H, br s), 2.24 (3H, s), 3.83 (2H, s), 6.76 (1H, dd, J = 8.1, 2.0 Hz), 6.87-6.93 (2H, m), 6.98-7.01 (1H, m), 7.05-7.10 (1H, m), 7.14-7.20 (1H, m), 7.24-7.28 (2H, m). Reference production example 3
0.61 g of 3-fluorobenzonitrile, 0.59 g of 2-methylphenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 20 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated by centrifugation under reduced pressure to give 0.87 g of 3- (2-methylphenyloxy) benzonitrile.
0.31 g of 3- (2-methylphenyloxy) benzonitrile was added to 1 ml of THF, 1 ml of a THF solution of lithium aluminum hydride (2.0 M) was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.31 g of 3- (2-methylphenyloxy) benzylamine.
3- (2-Methylphenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.40 (2H, br s), 2.24 (3H, s), 3.83 (2H, s), 6.76 (1H, dd, J = 8.1, 2.0 Hz), 6.87-6.93 ( 2H, m), 6.98-7.01 (1H, m), 7.05-7.10 (1H, m), 7.14-7.20 (1H, m), 7.24-7.28 (2H, m).

¹H-NMR (CDCl₃) δ: 1.43 (2H, br s), 3.85 (2H, s), 6.84 (1H, dd, J = 8.2, 2.1 Hz), 6.94-6.96 (1H, m), 7.03-7.21 (5H, m), 7.26-7.30 (1H, m). Reference production example 4
0.61 g of 3-fluorobenzonitrile, 0.62 g of 2-fluorophenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 20 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed sequentially with water and saturated brine, dried over magnesium sulfate, and then concentrated by centrifugation under reduced pressure to obtain 0.90 g of 3- (2-fluorophenyloxy) benzonitrile.
0.32 g of 3- (2-fluorophenyloxy) benzonitrile was added to 1 ml of THF, 1 ml of a lithium aluminum hydride solution (2.0 M) was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.32 g of 3- (2-fluorophenyloxy) benzylamine.
3- (2-Fluorophenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.43 (2H, br s), 3.85 (2H, s), 6.84 (1H, dd, J = 8.2, 2.1 Hz), 6.94-6.96 (1H, m), 7.03- 7.21 (5H, m), 7.26-7.30 (1H, m).

¹H-NMR (CDCl₃) δ: 1.45 (2H, br s), 3.86 (2H, s), 6.87 (1H, dd, J = 8.1, 2.0 Hz), 6.92-6.97 (3H, m), 7.06-7.09 (1H, m), 7.26-7.32 (3H, m). Reference production example 5
0.61 g of 3-fluorobenzonitrile, 0.70 g of 2-chlorophenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 20 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and then concentrated by centrifugation under reduced pressure to obtain 0.99 g of 3- (2-chlorophenyloxy) benzonitrile.
0.34 g of 3- (2-chlorophenyloxy) benzonitrile was added to 1 ml of THF, and 1 ml of a solution of lithium aluminum hydride in THF (2.0 M) was added dropwise at 0 ° C., followed by stirring at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.34 g of 3- (2-chlorophenyloxy) benzylamine.
3- (2-Chlorophenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.45 (2H, br s), 3.86 (2H, s), 6.87 (1H, dd, J = 8.1, 2.0 Hz), 6.92-6.97 (3H, m), 7.06- 7.09 (1H, m), 7.26-7.32 (3H, m).

¹H-NMR (CDCl₃) δ: 1.45 (2H, br s), 3.87 (2H, s), 6.87-6.92 (2H, m), 6.97-7.01 (2H, m), 7.05-7.12 (2H, m), 7.22-7.26 (1H, m), 7.30-7.34 (1H, m). Reference production example 6
0.61 g of 3-fluorobenzonitrile, 0.70 g of 3-chlorophenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 20 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated by centrifugation under reduced pressure to give 0.97 g of 3- (3-chlorophenyloxy) benzonitrile.
0.34 g of 3- (3-chlorophenyloxy) benzonitrile was added to 1 ml of THF, 1 ml of a lithium aluminum hydride solution (2.0 M) was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.34 g of 3- (3-chlorophenyloxy) benzylamine.
3- (3-Chlorophenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.45 (2H, br s), 3.87 (2H, s), 6.87-6.92 (2H, m), 6.97-7.01 (2H, m), 7.05-7.12 (2H, m ), 7.22-7.26 (1H, m), 7.30-7.34 (1H, m).

¹H-NMR (CDCl₃) δ: 1.43 (2H, br s), 3.88 (2H, s), 6.84-6.87 (1H, m), 6.89-6.97 (3H, m), 7.00-7.03 (1H, m), 7.10-7.14 (1H, m), 7.30-7.36 (2H, m). Reference production example 7
0.61 g of 3-fluorobenzonitrile, 0.98 g of 3-trifluoromethoxyphenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 20 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated by centrifugation under reduced pressure to give 1.10 g of 3- (3-trifluoromethoxyphenyloxy) benzonitrile.
0.42 g of 3- (3-trifluoromethoxyphenyloxy) benzonitrile was added to 1 ml of THF, and 1 ml of a lithium aluminum hydride solution (2.0 M) was added dropwise at 0 ° C., followed by stirring at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.40 g of 3- (3-trifluoromethoxyphenyloxy) benzylamine.
3- (3-Trifluoromethoxyphenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.43 (2H, br s), 3.88 (2H, s), 6.84-6.87 (1H, m), 6.89-6.97 (3H, m), 7.00-7.03 (1H, m ), 7.10-7.14 (1H, m), 7.30-7.36 (2H, m).

¹H-NMR (CDCl₃) δ: 1.50 (2H, br s), 3.87 (2H, s), 6.89 (1H, dd, J = 8.1, 1.8 Hz), 6.98-7.02 (3H, m), 7.08-7.11 (1H, m), 7.16-7.20 (2H, m), 7.30-7.34 (1H, m). Reference production example 8
0.61 g of 3-fluorobenzonitrile, 0.98 g of 4-trifluoromethoxyphenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 8 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and then concentrated by centrifugation under reduced pressure to give 1.13 g of 3- (4-trifluoromethoxyphenyloxy) benzonitrile.
0.42 g of 3- (4-trifluoromethoxyphenyloxy) benzonitrile was added to 1 ml of THF, 1 ml of a lithium aluminum hydride solution (2.0 M) was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.35 g of 3- (4-trifluoromethoxyphenyloxy) benzylamine.
3- (4-Trifluoromethoxyphenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.50 (2H, br s), 3.87 (2H, s), 6.89 (1H, dd, J = 8.1, 1.8 Hz), 6.98-7.02 (3H, m), 7.08- 7.11 (1H, m), 7.16-7.20 (2H, m), 7.30-7.34 (1H, m).

¹H-NMR (CDCl₃) δ: 7.09 (2H, d, J = 8.5 Hz), 7.33 (1H, ddd, J = 8.1, 2.5, 1.0 Hz), 7.53-7.71 (5H, m), 9.99 (1H, s).
３−（４−トリフルオロメチルフェニルオキシ）ベンズアルデヒド６．５ｇ、ヒドロキシルアミン塩酸塩２．５ｇ、エタノール５０ｍｌ及び水２．４ｇを混合して、室温で２時間攪拌した後、１晩放置した。反応混合物に１０モル／Ｌ塩酸２．５ｍｌ及び１０％パラジウム炭素３．０ｇを加え、常圧水素雰囲気下で１０時間攪拌した。反応混合物をセライト（登録商標）でろ過し、ろ液を減圧下濃縮した。残渣を水及びＭＴＢＥで洗浄し、３−（４−トリフルオロメチルフェニルオキシ）ベンジルアミン塩酸塩４．９ｇを得た。
３−（４−トリフルオロメチルフェニルオキシ）ベンジルアミン塩酸塩

¹H-NMR (CDCl₃) δ: 1.52 (3H, br s), 3.88 (2H, s), 6.93 (1H, dd, J = 8.0, 2.0 Hz), 7.02-7.06 (3H, m), 7.14 (1H, dd, J = 7.6, 0.5 Hz), 7.34 (1H, dd, J = 8.0, 7.6 Hz), 7.57 (2H, d, J = 8.5 Hz). Reference production example 9
A mixture of 27 g of 4-chlorobenzotrifluoride, 12 g of 3-hydroxybenzaldehyde, 12.3 g of potassium 1,1-dimethylethoxide, 4.3 g of copper (I) bromide and 150 ml of DMF was heated to reflux for 2 hours. Water and ethyl acetate were added to the reaction mixture which was allowed to cool to near room temperature, and then filtered through Celite (registered trademark) to separate the organic layer. The organic layer was washed successively with hydrochloric acid, water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 6.5 g of 3- (4-trifluoromethylphenyloxy) benzaldehyde.
3- (4-Trifluoromethylphenyloxy) benzaldehyde

¹ H-NMR (CDCl ₃ ) δ: 7.09 (2H, d, J = 8.5 Hz), 7.33 (1H, ddd, J = 8.1, 2.5, 1.0 Hz), 7.53-7.71 (5H, m), 9.99 (1H , s).
After mixing 6.5 g of 3- (4-trifluoromethylphenyloxy) benzaldehyde, 2.5 g of hydroxylamine hydrochloride, 50 ml of ethanol and 2.4 g of water, the mixture was stirred at room temperature for 2 hours and then left overnight. To the reaction mixture, 2.5 ml of 10 mol / L hydrochloric acid and 3.0 g of 10% palladium carbon were added, and the mixture was stirred for 10 hours under an atmospheric hydrogen atmosphere. The reaction mixture was filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. The residue was washed with water and MTBE to obtain 4.9 g of 3- (4-trifluoromethylphenyloxy) benzylamine hydrochloride.
3- (4-Trifluoromethylphenyloxy) benzylamine hydrochloride

¹ H-NMR (CDCl ₃ ) δ: 1.52 (3H, br s), 3.88 (2H, s), 6.93 (1H, dd, J = 8.0, 2.0 Hz), 7.02-7.06 (3H, m), 7.14 ( 1H, dd, J = 7.6, 0.5 Hz), 7.34 (1H, dd, J = 8.0, 7.6 Hz), 7.57 (2H, d, J = 8.5 Hz).

¹H-NMR (CDCl₃) δ: 2.37 (3H, s), 6.91-6.95 (2H, m), 7.16-7.22 (4H, m), 7.31-7.41 (2H, m).
水素化リチウムアルミニウム１．８ｇ及びＴＨＦ５０ｍｌの混合溶液に、３−（４−メチルフェニルオキシ）ベンゾニトリル８．０ｇをＴＨＦ５ｍｌに溶かした溶液を０℃で滴下した。室温で４時間攪拌した後、反応混合物に水、１５％水酸化ナトリウム水溶液及び水を順次加え、室温で１晩放置した。混合液をセライト（登録商標）でろ過し、ろ液を減圧下濃縮した。残渣にＭＴＢＥ及び炭酸カリウムを加え、セライト（登録商標）でろ過し、ろ液を減圧下濃縮し、３−（４−メチルフェニルオキシ）ベンジルアミン７．０ｇを得た。
３−（４−メチルフェニルオキシ）ベンジルアミン

¹H-NMR (CDCl₃) δ: 1.40 (2H, br s), 2.33 (3H, s), 3.82 (2H, s), 6.82-6.87 (1H, m), 6.89-6.95 (3H, m), 6.99-7.03 (1H, m), 7.11-7.15 (2H, m), 7.24-7.28 (1H, m). Reference production example 10
A mixture of 5.0 g of 3-fluorobenzonitrile, 5.3 g of 4-methylphenol, 17.5 g of cesium carbonate and 30 ml of DMF was heated to reflux for 4 hours. Water and ethyl acetate were added to the reaction mixture which was allowed to cool to near room temperature, followed by filtration through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 8.0 g of 3- (4-methylphenyloxy) benzonitrile.
3- (4-Methylphenyloxy) benzonitrile

¹ H-NMR (CDCl ₃ ) δ: 2.37 (3H, s), 6.91-6.95 (2H, m), 7.16-7.22 (4H, m), 7.31-7.41 (2H, m).
A solution prepared by dissolving 8.0 g of 3- (4-methylphenyloxy) benzonitrile in 5 ml of THF was added dropwise to a mixed solution of 1.8 g of lithium aluminum hydride and 50 ml of THF at 0 ° C. After stirring at room temperature for 4 hours, water, a 15% aqueous sodium hydroxide solution and water were sequentially added to the reaction mixture, and the mixture was allowed to stand overnight at room temperature. The mixture was filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. MTBE and potassium carbonate were added to the residue, filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure to obtain 7.0 g of 3- (4-methylphenyloxy) benzylamine.
3- (4-Methylphenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.40 (2H, br s), 2.33 (3H, s), 3.82 (2H, s), 6.82-6.87 (1H, m), 6.89-6.95 (3H, m), 6.99-7.03 (1H, m), 7.11-7.15 (2H, m), 7.24-7.28 (1H, m).

¹H-NMR (CDCl₃) δ: 1.43 (2H, br s), 3.86 (2H, s), 6.86-6.88 (1H, m), 6.92-6.96 (3H, m), 7.07 (1H, d, J = 7.6 Hz), 7.28-7.32 (3H, m). Reference production example 11
0.61 g of 3-fluorobenzonitrile, 0.70 g of 4-chlorophenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 20 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed successively with aqueous sodium hydroxide solution and saturated brine, dried over magnesium sulfate, and concentrated by centrifugation under reduced pressure to give 1.00 g of 3- (4-chlorophenyloxy) benzonitrile.
0.34 g of 3- (4-chlorophenyloxy) benzonitrile was added to 1 ml of THF, 1 ml of a THF solution of lithium aluminum hydride (2.0 M) was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.34 g of 3- (4-chlorophenyloxy) benzylamine.
3- (4-Chlorophenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.43 (2H, br s), 3.86 (2H, s), 6.86-6.88 (1H, m), 6.92-6.96 (3H, m), 7.07 (1H, d, J = 7.6 Hz), 7.28-7.32 (3H, m).

¹H-NMR (CDCl₃) δ: 1.78 (2H, br s), 3.88 (2H, s), 6.94-6.96 (2H, m), 7.03-7.08 (4H, m), 7.28-7.30 (2H, m). Reference production example 12
0.61 g of 3-fluorobenzonitrile, 0.89 g of 2-trifluoromethylphenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 20 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed successively with aqueous sodium hydroxide solution and saturated brine, dried over magnesium sulfate, and concentrated by centrifugation under reduced pressure to give 0.43 g of 3- (2-trifluoromethylphenyloxy) benzonitrile.
0.40 g of 3- (2-trifluoromethylphenyloxy) benzonitrile was added to 1 ml of THF, and 1 ml of a lithium aluminum hydride solution (2.0 M) was added dropwise at 0 ° C., followed by stirring at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The reaction mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.32 g of 3- (2-trifluoromethylphenyloxy) benzylamine.
3- (2-trifluoromethylphenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.78 (2H, br s), 3.88 (2H, s), 6.94-6.96 (2H, m), 7.03-7.08 (4H, m), 7.28-7.30 (2H, m ).

¹H-NMR (CDCl₃) δ: 1.43 (2H, br s), 3.88 (2H, s), 6.90 (1H, dd, J = 8.1, 2.0 Hz), 7.01 (1H, s), 7.13-7.16 (2H, m), 7.24 (1H, s), 7.32-7.36 (2H, m), 7.43-7.45 (1H, m). Reference production example 13
0.61 g of 3-fluorobenzonitrile, 0.89 g of 2-trifluoromethylphenol and 1.95 g of cesium carbonate were added to 5 ml of DMF, and the mixture was heated to reflux for 20 hours. Dilute hydrochloric acid was added to the reaction mixture which was allowed to cool to near room temperature, and extracted with diethyl ether. The organic layer was washed successively with an aqueous sodium hydroxide solution and saturated brine, dried over magnesium sulfate, and concentrated by centrifugation under reduced pressure to give 1.10 g of 3- (3-trifluoromethylphenyloxy) benzonitrile.
0.40 g of 3- (3-trifluoromethylphenyloxy) benzonitrile was added to 1 ml of THF, 1 ml of a lithium aluminum hydride solution (2.0 M) was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture, 1 ml of ethanol, 1 ml of water and 1 ml of 15% sodium hydroxide aqueous solution were successively added dropwise at 0 ° C. The reaction mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure to obtain 0.32 g of 3- (3-trifluoromethylphenyloxy) benzylamine.
3- (3-Trifluoromethylphenyloxy) benzylamine

¹ H-NMR (CDCl ₃ ) δ: 1.43 (2H, br s), 3.88 (2H, s), 6.90 (1H, dd, J = 8.1, 2.0 Hz), 7.01 (1H, s), 7.13-7.16 ( 2H, m), 7.24 (1H, s), 7.32-7.36 (2H, m), 7.43-7.45 (1H, m).

  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 any one of the present compounds 1 to 19, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide.

Formulation Example 2
20 parts of any one of the compounds 1 to 19 of the present invention 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. 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 stirred to obtain a flowable preparation.

Formulation Example 3
A powder is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compounds 1 to 19 of the present invention, 88 parts of kaolin clay and 10 parts of talc.

Formulation Example 4
An emulsion is obtained by thoroughly mixing 5 parts of any one of the compounds 1 to 19 of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.

Formulation Example 5
After thoroughly mixing 2 parts of any one of the compounds 1 to 19 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, water is added and kneaded well. Granules are obtained by granulating and drying.

Formulation Example 6
Formulation by mixing 10 parts of any one of the present compounds 1 to 19; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; Get.

Next, test examples show that the present invention is useful for controlling plant diseases.
The control effect is to visually observe the area of the lesion on the test plant at the time of the survey, and to compare the area of the lesion on the plant treated with the present control agent and the area of the lesion on the untreated plant. It was evaluated by.

をあわせて試験に供試した As a control, N-[(3-phenoxy) phenyl] methyl-2-aminonicotinic acid amide (a compound represented by the following formula (A) described in Examples of WO 2005/033079 pamphlet. (Referred to as compound (A))

And used for the test

Test example 1
Cucumber powdery mildew prevention effect test (Sphaerotheca furiginea)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. Thereafter, the compound 17 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 on the foliage so as to adhere well to the leaf surface of the cucumber. After spraying, the plants were air-dried and sprinkled with spores of pathogenic bacteria. After inoculation, it was placed in a 23 ° C. greenhouse for 10 days, and then the lesion area was examined.
As a result, the lesion area in the plant treated with the compound 17 of the present invention was 30% or less of the lesion area in the untreated plant.

Test example 2
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. The present compounds 12, 13, 16, 17, 18, and 19 were made into flowable preparations according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and the foliage so as to adhere well to the leaves of the wheat. Scattered. After spraying, the plants were air-dried, and two days later, a water suspension of wheat leaf blight fungus spores was spray-inoculated. After the inoculation, it was 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 which processed this invention compound 12, 13, 16, 17, 18, and 19 was 30% or less of the lesion area in an untreated plant.
The lesion area in the plant treated with the comparative compound (A) was 75% or more 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. The compounds 1 and 19 of the present invention were made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed on the 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 and 19 was 30% or less of the lesion area in the untreated plant.

Test example 4
Test for prevention of kidney bean nuclear disease (Sclerotinia sclerotiorum)
A plastic pot was stuffed with sand loam, seeded with green beans (variety; long bean) and grown in a greenhouse for 8 days. After making this invention compound 4, 9, 12, 13, 15, 16, and 17 into a flowable preparation according to Preparation Example 6, it is diluted with water to a predetermined concentration (500 ppm) so that it adheres well to the kidney leaf surface. The foliage was sprayed. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of sclerotia sclerotium was placed on the kidney leaf surface. After the inoculation, all kidney beans were left 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 which processed this invention compound 4, 9, 12, 13, 15, 16, and 17 was 30% or less of the lesion area in an untreated plant.

Test Example 5
Cucumber downy mildew treatment effect test (Pseudoperonospora cubensis)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The pot was spray-inoculated with an aqueous suspension of cucumber downy mildew zoosporangium, placed at 23 ° C. under high humidity for 1 day, and then air-dried to obtain a cucumber downy mildew-infected seedling. The compounds 2, 4, 5, 6, 7, 13 and 17 of the present invention are made into flowable preparations according to Preparation Example 6, and then diluted with water to a predetermined concentration (500 ppm), which adheres well to the leaves of the cucumber seedlings. So that the foliage was sprayed. After spraying, the plants were air-dried, placed in a greenhouse at 23 ° C. for 5 days, and further placed at 23 ° C. and humid for 1 day, and then the lesion area was examined.
As a result, the lesion area in the plant which processed this invention compound 2, 4, 5, 6, 7, 13, and 17 was 30% or less of the lesion area in an untreated plant.

Test Example 6
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. The compounds 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 17, and 18 of the present invention were made into flowable preparations according to Preparation Example 6 and then diluted with water to give The concentration (500 ppm) was applied, and the foliage was sprayed so as to adhere well to the leaf surface of the tomato seedling. After air-dried to such an extent that the diluted solution on the leaf surface was dried, the suspension was spray-inoculated with an aqueous suspension of tomato plague fungus spores. After inoculation, it was 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 plants treated with the compounds 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 17 and 18 of the present invention is as follows. It was 30% or less of the lesion area.
The lesion area in the plant treated with the comparative compound (A) was 75% or more of the lesion area in the untreated plant.

Test Example 7
Rice blast prevention effect test (Magnaporthe grisea)
A plastic pot was filled with soil, rice (cultivar; Nipponbare) was sown and grown in a greenhouse for 12 days. The compounds 2, 3, 4, 5, 9, 14, 18 and 19 of the present invention were made into flowable preparations according to Preparation Example 6 and then diluted with water to a predetermined concentration (500 ppm). The foliage was sprayed like so. After spraying, the plants were air-dried, and a pot having rice blast diseased leaves was left around the sprayed plants. All rice was left under high humidity only at night, and the lesion area was examined 5 days after inoculation.
As a result, the lesion area in the plant which processed this invention compound 2, 3, 4, 5, 9, 14, 18 and 19 was 30% or less of the lesion area in an untreated plant.
The lesion area in the plant treated with the comparative compound (A) was 75% or more of the lesion area in the untreated plant.

Test Example 8
Tomato wilt soil treatment test (irrigation)
Tomato wilt (Fusarium oxysporum) contaminated soil is packed in a plastic pot, tomato (variety: patio) is seeded, and the present compounds 1 to 18 and 19 are made into flowable preparations according to Preparation Example 6, and then diluted with water. Soil irrigation treatment is carried out with an amount of the water dilution of 10 mg of the present compound per one pot of the plastic pot. After cultivating in a greenhouse for 1 month, investigate the growth of plants.
As a result, the plants cultivated in the soil (treated area) in which the present compounds 1 to 18 and 19 were subjected to soil irrigation treatment were treated in the same manner as the treated area in the soil not subjected to the soil irrigation treatment (non-treated area). It can be confirmed that the symptom of tomato wilt is reduced as compared with the cultivated plant.

Test Example 9
Potato half body wilt soil treatment test (irrigation)
A plastic pot is filled with soil contaminated with potato half body wilt (Verticillium albo-atrum, v. Dahliae, v. Nigrescens), potatoes (variety: baron) are planted, and compounds 1-18 and 19 of the present invention are formulated according to Formulation Example 6. The flowable preparation is diluted with water, and the water-diluted solution in an amount of 10 mg of the present compound per 1 pot of the plastic pot is subjected to soil irrigation treatment. After cultivating in a greenhouse for 2 months, investigate the growth of plants.
As a result, plants cultivated in soil (treated area) in which the present compounds 1 to 18 and 19 were subjected to soil irrigation treatment were treated in the same manner as the treated area in soil (non-treated area) in which the present compound was not subjected to soil irrigation treatment. Compared with the cultivated plant, it can be confirmed that the symptoms of potato half body wilt disease are reduced.

Test Example 10
Rice diabetic seed treatment test Compounds 1 to 18 and 19 of the present invention were made into flowable preparations according to Formulation Example 6 and then diluted to 2000 ppm with water to immerse rice diabetic fungi (Gibberella fujikuroi) -contaminated pods by the immersion method. Treat the seeds. Thereafter, the seedling box filled with soil is sown with the above-mentioned contaminated pods and cultivated in a greenhouse for one month, and then the growth state of the plant is investigated.
As a result, plants grown by seed treatment of the present compounds 1 to 18 and 19 (treated areas) were compared to plants grown without treatment (treated areas) in the same manner as the treated areas (rice-treated areas). It can be confirmed that the symptoms of the disease are reduced.

Test Example 11
Wheat root blight seed treatment test After the present compounds 1 to 18 and 19 were made into flowable preparations according to Formulation Example 6, the amount of the present compound was 200 g per 100 kg seeds on wheat blight fungus (Gaeumanomyces graminis) contaminated seeds. The flowable preparation is seed-treated by a smearing method using a seed dresser. Thereafter, the contaminated seeds treated with the seeds are sown in a plastic pot filled with sandy loam, cultivated in a greenhouse for one month, and then the growth state of the plants is investigated.
As a result, plants cultivated by treating seeds 1 to 18 and 19 of the present invention (treated area) withered wheat as compared to plants cultivated in the same manner as the treated area without seed treatment (untreated area). It can be confirmed that the symptoms of the disease are reduced.

Claims (5)

Formula (1)

[Where,
R ¹ represents a hydrogen atom, a fluorine atom, a C1-C3 alkyl group or a (C1-C3 alkoxy) C1-C3 alkyl group,
R ² represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group, a trifluoromethyl group or a trifluoromethoxy group. ]
An amide compound represented by Trifluoromethyl group R ² is bonded to the 3-position, 4-position trifluoromethyl group attached to, according to claim 1 is trifluoromethoxy groups attached to the trifluoromethoxy group or a 4-position bound to the 3-position Amide compounds.   A plant disease control agent comprising the amide compound according to claim 1 or 2 and a carrier.   A method for controlling plant diseases comprising a step of treating an effective amount of the amide compound according to claim 1 or 2 to a plant or soil.   Use of the amide compound according to claim 1 or 2 for controlling plant diseases.