JP2010095522A - Agricultural composition for controlling or preventing plant diseases caused by plant pathogenic bacteria - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an agricultural composition for controlling or preventing plant diseases caused by plant pathogenic bacteria. <P>SOLUTION: The agricultural composition containing an ether compound represented by formula (1), [wherein A represents A<SP>1</SP>, A<SP>2</SP>, or A<SP>3</SP>, n is any one of integers 1 to 4, E represents an optionally substituted furyl, thienyl, pyrrolyl, tetrazolyl, thiazolyl, pyrazolyl or phenyl group], its salts or their hydrates controls or prevents plant diseases caused by pathogenic bacteria. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention provides an agricultural composition containing an ether compound or a salt thereof or a hydrate thereof for controlling or preventing plant diseases caused by plant pathogens, and an effective amount of the agricultural composition is applied to useful crops. The present invention relates to a method for controlling or preventing plant diseases caused by plant pathogens.

  Conventionally, agricultural compositions for controlling or preventing plant diseases caused by plant pathogens have been developed and put into practical use. Certain ether compounds are also known. (For example, refer to Patent Documents 1 and 2 and Non-Patent Document 1.)

International Patent Application WO2005 / 033079 Pamphlet International Patent Application WO2007 / 088978 Pamphlet

Shibuya Narumi, Kawamata Hiroshi, Kawamata Mariko, Shimazaki Isao, “SHIBUYA INDEX” -2005- (10th Edition), published by SHIBUYA INDEX Study Group

  This invention makes it a subject to provide the agricultural composition for controlling or preventing the plant disease by a plant pathogen which has the outstanding efficacy.

〔式中、
Ａは、下記のＡ¹、Ａ²またはＡ³

（式中
ｐは、０から６までの整数のいずれかを表し、
ｑは、０から５までの整数のいずれかを表し、
ｒは、０から４までの整数のいずれかを表し、
Ｒ¹は、ハロゲン原子、Ｃ１−Ｃ４アルキル基又はシアノ基を表し、
Ｒ²は、ハロゲン原子、Ｃ１−Ｃ４アルキル基、Ｃ１−Ｃ４アルコキシ基又はシアノ基を表し、
Ｒ³は、ハロゲン原子、Ｃ１−Ｃ４アルキル基、Ｃ１−Ｃ４アルコキシ基又はシアノ基を表す。
ただし、ｐが２から６までの整数である場合、各々のＲ¹は互いに同一又は相異なり、ｑが２から５までの整数である場合、各々のＲ²は互いに同一又は相異なり、ｒが２から４までの整数である場合、各々のＲ³は互いに同一又は相異なる。）を表し、
ｎは、１〜４までの整数のいずれかを表し、
Ｅは、フリル基、チエニル基、ピロリル基、テトラゾリル基、チアゾリル基、ピラゾリル
基またはフェニル基を表し、
Ｅで示される基はいずれも、以下の置換基群ａ−１および置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよい；
［置換基群ａ−１］
ハロゲン原子、アミノ基、水酸基、メルカプト基、シアノ基、ホルミル基、カルボキシル基、Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ３−８シクロアルキル基、Ｃ６−１０アリール基、５−１０員ヘテロ環式基、Ｃ３−８シクロアルキルＣ１−６アルキル基、Ｃ３−８シクロアルキリデンＣ１−６アルキル基、Ｃ６−１０アリールＣ１−６アルキル基、Ｃ６−１０アリールＣ２−６アルケニル基、５−１０員ヘテロ環Ｃ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ３−８シクロアルコキシ基、Ｃ６−１０アリールオキシ基、５−１０員ヘテロ環オキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、Ｃ６−１０アリールＣ１−６アルコキシ基、５−１０員ヘテロ環Ｃ１−６アルコキシ基、Ｃ１−８アルキルチオ基、Ｃ２−８アルケニルチオ基、Ｃ２−８アルキニルチオ基、Ｃ３−８シクロアルキルチオ基、Ｃ６−１０アリールチオ基、Ｃ３−８シクロアルキルＣ１−６アルキルチオ基 、Ｃ６−１０アリールＣ１−６アルキルチオ基、５−１０員ヘテロ環Ｃ１−６アルキルチオ基、モノ−Ｃ１−６アルキルアミノ基、モノ−Ｃ２−６アルケニルアミノ基、モノ−Ｃ２−６アルキニルアミノ基、モノ−Ｃ３−８シクロアルキルアミノ基、モノ−Ｃ６−１０アリールアミノ基、モノ−Ｃ３−８シクロアルキルＣ１−６アルキルアミノ基、モノ−Ｃ６−１０アリールＣ１−６アルキルアミノ基、モノ−５−１０ 員ヘテロ環Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルケニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルキニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリール−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキルＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリールＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−５−１０員ヘテロ環Ｃ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｃ１−６アルキルカルボニル基、Ｃ６−１０アリールカルボニル基、Ｃ１−６アルコキシカルボニル基、Ｃ１−６アルキルスルホニル基、Ｃ１−６アルキルスルフィニル基、式−Ｃ（＝Ｎ−Ｒ^a1）Ｒ^a2で表される基（式中、Ｒ^a1は、水酸基またはＣ１−６アルコキシ基を意味する；Ｒ^a2は、水素原子またはＣ１−６アルキル基を意味する。）、Ｃ６−１０アリールオキシＣ１−６アルキル基、５−１０員ヘテロ環オキシＣ１−６アルキル基およびＣ１−３トリアルキルシリルＣ２−８アルキニル基；
［置換基群ａ−２］
Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ３−８シクロアルキル基、Ｃ６−１０アリール基、５−１０員ヘテロ環式基、Ｃ３−８シクロアルキルＣ１−６アルキル基、Ｃ６−１０アリールＣ１−６アルキル基、５−１０員ヘテロ環Ｃ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ３−８シクロアルコキシ基、Ｃ６−１０アリールオキシ基、５−１０員ヘテロ環オキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、Ｃ６−１０アリールＣ１−６アルコキシ基、５−１０員ヘテロ環Ｃ１−６アルコキシ基、Ｃ１−８アルキルチオ基、Ｃ２−８アルケニルチオ基、Ｃ２−８アルキニルチオ基、Ｃ３−８シクロアルキルチオ基、Ｃ６−１０アリールチオ基、Ｃ３−８シクロアルキルＣ１−６アルキルチオ基 、Ｃ６−１０アリールＣ１−６アルキルチオ基、５−１０員ヘテロ環Ｃ１−６アルキルチオ基、モノ−Ｃ１−６アルキルアミノ基、モノ−Ｃ２−６アルケニルアミノ基、モノ−Ｃ２−６アルキニルアミノ基、モノ−Ｃ３−８シクロアルキルアミノ基、モノ−Ｃ６−１０アリールアミノ基、モノ−Ｃ３−８シクロアルキルＣ１−６アルキルアミノ基、モノ−Ｃ６−１０アリールＣ１−６アルキルアミノ基、モノ−５−１０員ヘテロ環Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルケニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルキニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリール−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキルＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリールＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−５−１０員ヘテロ環Ｃ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｃ６−１０アリールオキシＣ１−６アルキル基および５−１０員ヘテロ環オキシＣ１−６アルキル基；
ただし、前記の置換基群ａ−２に記載の各基は、以下の置換基群ｂ−１から選ばれる置換基を１ないし３個有する；
［置換基群ｂ−１］
ハロゲン原子、水酸基、メルカプト基、シアノ基、カルボキシル基、アミノ基、カルバモイル基、ニトロ基、Ｃ１−６アルキル基、Ｃ３−８シクロアルキル基、Ｃ６−１０アリール基、５−１０員ヘテロ環式基、Ｃ１−６アルコキシ基、Ｃ６−１０アリールオキシ基、５−１０員ヘテロ環オキシ基、Ｃ１−６アルコキシカルボニル基、Ｃ１−８アルキルチオ基、Ｃ１−６アルキルスルホニル基、トリフルオロメチル基、トリフルオロメトキシ基、モノ−Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、アミノ基またはアミノスルホニル基を1個有していてもよいモノ−Ｃ６−１０アリールアミノ基およびアミノ基を1個有していてもよいＮ−Ｃ６−１０アリールＣ１−６ アルキル−Ｎ−Ｃ１−６アルキルアミノ基〕
で表される化合物もしくはその塩またはそれらの水和物（以下、本化合物と記す場合もある。）を含有する農業用組成物（以下、本発明農業用組成物と記す場合もある。）、
（２）本発明農業用組成物の有効量を有用作物に施用する、植物病原菌による植物病害を防除又は予防する方法、
（３）本発明農業用組成物を製造するための、本化合物もしくはその塩またはそれらの水和物の使用等を提供するものである。
より詳しくは、本発明は以下の１．〜１８．の通りである。
１． 植物病原菌（但し、アスペルギルス（Ａｓｐｅｒｇｉｌｌｕｓ）を除く。）による植物病害を防除するための、
式（１）

〔式中、
Ａは、下記のＡ¹、Ａ²またはＡ³

（式中
ｐは、０から６までの整数のいずれかを表し、
ｑは、０から５までの整数のいずれかを表し、
ｒは、０から４までの整数のいずれかを表し、
Ｒ¹は、ハロゲン原子、Ｃ１−Ｃ４アルキル基又はシアノ基を表し、
Ｒ²は、ハロゲン原子、Ｃ１−Ｃ４アルキル基、Ｃ１−Ｃ４アルコキシ基又はシアノ基を表し、
Ｒ³は、ハロゲン原子、Ｃ１−Ｃ４アルキル基、Ｃ１−Ｃ４アルコキシ基又はシアノ基を表す。
ただし、ｐが２から６までの整数である場合、各々のＲ¹は互いに同一又は相異なり、ｑが２から５までの整数である場合、各々のＲ²は互いに同一又は相異なり、ｒが２から４までの整数である場合、各々のＲ³は互いに同一又は相異なる。）を表し、
ｎは、１〜４までの整数のいずれかを表し、
Ｅは、フリル基、チエニル基、ピロリル基、テトラゾリル基、チアゾリル基、ピラゾリル
基またはフェニル基を表し、
Ｅで示される基はいずれも、以下の置換基群ａ−１および置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよい；
［置換基群ａ−１］
ハロゲン原子、アミノ基、水酸基、メルカプト基、シアノ基、ホルミル基、カルボキシル基、Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ３−８シクロアルキル基、Ｃ６−１０アリール基、５−１０員ヘテロ環式基、Ｃ３−８シクロアルキルＣ１−６アルキル基、Ｃ３−８シクロアルキリデンＣ１−６アルキル基、Ｃ６−１０アリールＣ１−６アルキル基、Ｃ６−１０アリールＣ２−６アルケニル基、５−１０員ヘテロ環Ｃ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ３−８シクロアルコキシ基、Ｃ６−１０アリールオキシ基、５−１０員環オキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、Ｃ６−１０アリールＣ１−６アルコキシ基、５−１０員ヘテロ環Ｃ１−６アルコキシ基、Ｃ１−８アルキルチオ基、Ｃ２−８アルケニルチオ基、Ｃ２−８アルキニルチオ基、Ｃ３−８シクロアルキルチオ基、Ｃ６−１０アリールチオ基、Ｃ３−８シクロアルキルＣ１−６アルキルチオ基 、Ｃ６−１０アリールＣ１−６アルキルチオ基、５−１０員ヘテロ環Ｃ１−６アルキルチオ基、モノ−Ｃ１−６アルキルアミノ基、モノ−Ｃ２−６アルケニルアミノ基、モノ−Ｃ２−６アルキニルアミノ基、モノ−Ｃ３−８シクロアルキルアミノ基、モノ−Ｃ６−１０アリールアミノ基、モノ−Ｃ３−８シクロアルキルＣ１−６アルキルアミノ基、モノ−Ｃ６−１０アリールＣ１−６アルキルアミノ基、モノ−５−１０員ヘテロ環Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルケニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルキニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリール−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキルＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリールＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−５−１０員ヘテロ環Ｃ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｃ１−６アルキルカルボニル基、Ｃ６−１０アリールカルボニル基、Ｃ１−６アルコキシカルボニル基、Ｃ１−６アルキルスルホニル基、Ｃ１−６アルキルスルフィニル基、式−Ｃ（＝Ｎ−Ｒ^a1）Ｒ^a2で表される基（式中、Ｒ^a1は、水酸基またはＣ１−６アルコキシ基を意味する；Ｒ^a2は、水素原子またはＣ１−６アルキル基を意味する。）、Ｃ６−１０アリールオキシＣ１−６アルキル基、５−１０員ヘテロ環オキシＣ１−６アルキル基およびＣ１−Ｃ３トリアルキルシリルＣ２−８アルキニル基；
［置換基群ａ−２］
Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ３−８シクロアルキル基、Ｃ６−１０アリール基、５−１０員ヘテロ環式基、Ｃ３−８シクロアルキルＣ１−６アルキル基、Ｃ６−１０アリールＣ１−６アルキル基、５−１０員ヘテロ環Ｃ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ３−８シクロアルコキシ基、Ｃ６−１０アリールオキシ基、５−１０員へテロ環オキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、Ｃ６−１０アリールＣ１−６アルコキシ基、５−１０員ヘテロ環Ｃ１−６アルコキシ基、Ｃ１−８アルキルチオ基、Ｃ２−８アルケニルチオ基、Ｃ２−８アルキニルチオ基、Ｃ３−８シクロアルキルチオ基、Ｃ６−１０アリールチオ基、Ｃ３−８シクロアルキルＣ１−６アルキルチオ基 、Ｃ６−１０アリールＣ１−６アルキルチオ基、５−１０員ヘテロ環Ｃ１−６アルキルチオ基、モノ−Ｃ１−６アルキルアミノ基、モノ−Ｃ２−６アルケニルアミノ基、モノ−Ｃ２−６アルキニルアミノ基、モノ−Ｃ３−８シクロアルキルアミノ基、モノ−Ｃ６−１０アリールアミノ基、モノ−Ｃ３−８シクロアルキルＣ１−６アルキルアミノ基、モノ−Ｃ６−１０アリールＣ１−６アルキルアミノ基、モノ−５−１０員ヘテロ環Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルケニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルキニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリール−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキルＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリールＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−５−１０員ヘテロ環Ｃ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｃ６−１０アリールオキシＣ１−６アルキル基および５−１０員ヘテロ環オキシＣ１−６アルキル基；
ただし、前記の置換基群ａ−２に記載の各基は、以下の置換基群ｂ−１から選ばれる置換基を１ないし３個有する；
［置換基群ｂ−１］
ハロゲン原子、水酸基、メルカプト基、シアノ基、カルボキシル基、アミノ基、カルバモイル基、ニトロ基、Ｃ１−６アルキル基、Ｃ３−８シクロアルキル基、Ｃ６−１０アリール基、５−１０員ヘテロ環式基、Ｃ１−６アルコキシ基、Ｃ６−１０アリールオキシ基、５−１０員ヘテロ環オキシ基、Ｃ１−６アルコキシカルボニル基、Ｃ１−８アルキルチオ基、Ｃ１−６アルキルスルホニル基、トリフルオロメチル基、トリフルオロメトキシ基、モノ−Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、アミノ基またはアミノスルホニル基を1個有していてもよいモノ−Ｃ６−１０アリールアミノ基およびアミノ基を1個有していてもよいＮ−Ｃ６−１０アリールＣ１−６ アルキル−Ｎ−Ｃ１−６アルキルアミノ基〕
で表されるエーテル化合物もしくはその塩またはそれらの水和物を含有する農業用組成物。

２． 式（１）において、Ｅが、置換基群ａ−１および置換基群ａ−２から選ばれる少なくとも１種の基で置換されたフリル基、置換基群ａ−１および置換基群ａ−２から選ばれる少なくとも１種の基で置換されたチエニル基、置換基群ａ−１および置換基群ａ−２から選ばれる少なくとも１種の基で置換されたピロリル基または置換基群ａ−１および置換基群ａ−２から選ばれる少なくとも１種の基で置換されたフェニル基である１．記載の農業用組成物。

３． 式（１）において、Ｅが、以下の置換基群ａ−３および置換基群ａ−４から選ばれる少なくとも１種の基で置換されたフリル基、以下の置換基群ａ−３および置換基群ａ−４から選ばれる少なくとも１種の基で置換されたチエニル基、以下のａ−３および置換基群ａ−４から選ばれる少なくとも１種の基で置換されたピロリル基または以下の置換基群ａ−３および置換基群ａ−４から選ばれる少なくとも１種の基で置換されたフェニル基である１．記載の農業用組成物。
［置換基群ａ−３］
ハロゲン原子、水酸基、メルカプト基、シアノ基、カルボキシル基、Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ３−８シクロアルキル基、Ｃ６−１０アリール基、５−１０員ヘテロ環式基、Ｃ３−８シクロアルキルＣ１−６アルキル基、Ｃ３−８シクロアルキリデンＣ１−６アルキル基、Ｃ６−１０アリールＣ１−６アルキル基、５−１０員ヘテロ環Ｃ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ３−８シクロアルコキシ基、Ｃ６−１０アリールオキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、５−１０員ヘテロ環Ｃ１−６アルコキシ基、Ｃ１−８アルキルチオ基、Ｃ２−８アルケニルチオ基、Ｃ２−８アルキニルチオ基、Ｃ３−８シクロアルキルチオ基、Ｃ６−１０アリールチオ基、Ｃ３−８シクロアルキルＣ１−６アルキルチオ基 、Ｃ６−１０アリールＣ１−６アルキルチオ基、５−１０員ヘテロ環Ｃ１−６アルキルチオ基、モノ−Ｃ１−６アルキルアミノ基、モノ−Ｃ２−６アルケニルアミノ基、モノ−Ｃ２−６アルキニルアミノ基、モノ−Ｃ３−８シクロアルキルアミノ基、モノ−Ｃ６−１０アリールアミノ基、モノ−Ｃ３−８シクロアルキルＣ１−６アルキルアミノ基、モノ−Ｃ６−１０アリールＣ１−６アルキルアミノ基、モノ−５−１０ 員ヘテロ環Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルケニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルキニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリール−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキルＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリールＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−５−１０員ヘテロ環Ｃ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｃ１−６アルキルカルボニル基、Ｃ１−６アルコキシカルボニル基、Ｃ１−６アルキルスルホニル基、式−Ｃ（＝Ｎ−Ｒ^a1）Ｒ^a2で表される基（式中、Ｒ^a1は、水酸基またはＣ１−６アルコキシ基を意味する；Ｒ^a2は、水素原子またはＣ１−６アルキル基を意味する。）、Ｃ６−１０アリールオキシＣ１−６アルキル基および５−１０員ヘテロ環オキシＣ１−６アルキル基；
［置換基群ａ−４］
Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ３−８シクロアルキル基、Ｃ６−１０アリール基、５−１０員ヘテロ環式基、Ｃ３−８シクロアルキルＣ１−６アルキル基、Ｃ６−１０アリールＣ１−６アルキル基、５−１０員ヘテロ環Ｃ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ３−８シクロアルコキシ基、Ｃ６−１０アリールオキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、Ｃ６−１０アリールＣ１−６アルコキシ基、５−１０員ヘテロ環Ｃ１−６アルコキシ基、Ｃ１−８アルキルチオ基、Ｃ２−８アルケニルチオ基、Ｃ２−８アルキニルチオ基、Ｃ３−８シクロアルキルチオ基、Ｃ６−１０アリールチオ基、Ｃ３−８シクロアルキルＣ１−６アルキルチオ基 、Ｃ６−１０アリールＣ１−６アルキルチオ基、５−１０員ヘテロ環Ｃ１−６アルキルチオ基、モノ−Ｃ１−６アルキルアミノ基、モノ−Ｃ２−６アルケニルアミノ基、モノ−Ｃ２−６アルキニルアミノ基、モノ−Ｃ３−８シクロアルキルアミノ基、モノ−Ｃ６−１０アリールアミノ基、モノ−Ｃ３−８シクロアルキルＣ１−６アルキルアミノ基、モノ−Ｃ６−１０アリールＣ１−６アルキルアミノ基、モノ−５−１０員ヘテロ環Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルケニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ２−６アルキニル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリール−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ３−８シクロアルキルＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリールＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−５−１０員ヘテロ環Ｃ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｃ６−１０アリールオキシＣ１−６アルキル基および５−１０員ヘテロ環オキシＣ１−６アルキル基；
ただし、前記の置換基群ａ−４に記載の各基は、以下の置換基群ｂ−２から選ばれる置換基を１ないし３個有する；
［置換基群ｂ−２］
水酸基、メルカプト基、シアノ基、カルボキシル基、アミノ基、カルバモイル基、ニトロ基、Ｃ１−６アルキル基、Ｃ３−８シクロアルキル基、５−１０員ヘテロ環式基、Ｃ１−６アルコキシ基、Ｃ６−１０アリールオキシ基、５−１０員ヘテロ環オキシ基、Ｃ１−６アルコキシカルボニル基、Ｃ１−６アルキルスルホニル基、トリフルオロメチル基、トリフルオロメトキシ基、モノ−Ｃ１−６アルキルアミノ基、ジ−Ｃ１−６アルキルアミノ基、アミノ基またはアミノスルホニル基を1個有していてもよいモノ−Ｃ６−１０アリールアミノ基およびアミノ基を1個有していてもよいＮ−Ｃ６−１０アリールＣ１−６ アルキル−Ｎ−Ｃ１−６アルキルアミノ基〕

４． 式（１）において、Ｅが、以下の置換基群ｅ−１および置換基群ｅ−２から選ばれる置換基を１または２個有してもよいフリル基、以下の置換基群ｅ−１および置換基群ｅ−２から選ばれる置換基を１または２個有してもよいチエニル基、以下の置換基群ｅ−１および置換基群ｅ−２から選ばれる置換基を１または２個有してもよいピロリル基または以下の置換基群ｅ−１および置換基群ｅ−２から選ばれる置換基を１または２個有してもよいフェニル基である１．記載の農業用組成物。
〔［置換基群ｅ−１］
ハロゲン原子、Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ６−１０アリール基、Ｃ３−８シクロアルキルＣ１−６アルキル基、Ｃ３−８シクロアルキリデンＣ１−６アルキル基、Ｃ６−１０アリールＣ１−６アルキル基、Ｃ６−１０アリールＣ２−６アルケニル基、５−１０員ヘテロ環Ｃ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ６−１０アリールオキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、Ｃ６−１０アリールＣ１−６アルコキシ基、５−１０員ヘテロ環Ｃ１−６アルコキシ基、Ｃ６−１０アリールチオ基、Ｃ６−１０アリールＣ１−６アルキルチオ基、モノ−Ｃ６−１０アリールアミノ基、モノ−Ｃ６−１０アリールＣ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリール−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリールＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｃ６−１０アリールオキシＣ１−６アルキル基および５−１０員ヘテロ環オキシＣ１−６アルキル基；
［置換基群ｅ−２］
Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ６−１０アリール基、Ｃ３−８シクロアルキルＣ１−６アルキル基、Ｃ６−１０アリールＣ１−６アルキル基、５−１０員ヘテロ環Ｃ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ６−１０アリールオキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、Ｃ６−１０アリールＣ１−６アルコキシ基、５−１０員ヘテロ環Ｃ１−６アルコキシ基、Ｃ６−１０アリールチオ基、Ｃ６−１０アリ−ルＣ１−６アルキルチオ基、モノ−Ｃ６−１０アリールアミノ基、モノ−Ｃ６−１０アリールＣ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリール−Ｎ−Ｃ１−６アルキルアミノ基、Ｎ−Ｃ６−１０アリールＣ１−６アルキル−Ｎ−Ｃ１−６アルキルアミノ基、Ｃ６−１０アリールオキシＣ１−６アルキル基および５−１０員ヘテロ環オキシＣ１−６アルキル基；
ただし、前記の置換基群ｅ−２に記載の各基は、以下の置換基群ｆから選ばれる置換基を１ないし３個有する；
［置換基群ｆ］
ハロゲン原子、水酸基、シアノ基、アミノ基、ニトロ基、Ｃ３−８シクロアルキル基、Ｃ１−６アルコキシ基、Ｃ１−６アルキルチオ基、Ｃ６−１０アリールオキシ基、５−１０員ヘテロ環オキシ基、Ｃ１−６アルコキシカルボニル基、Ｃ１−６アルキルスルホニル基、モノ−Ｃ６−１０アリールアミノ基、トリフルオロメチル基、トリフルオロメトキシ基およびＣ１−６アルキル基〕

５． 式（１）において、Ｅが、以下の置換基群ｇ−１および置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフリル基、以下の置換基群ｇ−１および置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいチエニル基、以下の置換基群ｇ−１および置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいピロリル基または以下の置換基群ｇ−１および置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフェニル基である１．記載の農業用組成物。
〔［置換基群ｇ−１］
Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ３−８シクロアルキルＣ１−６アルキル基、フェニルＣ１−６アルキル基、フリルＣ１−６アルキル基、チエニルＣ１−６アルキル基、ベンゾフリルＣ１−６アルキル基、ベンゾチエニルＣ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、フェノキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、フェニルＣ１−６アルコキシ基、フリルＣ１−６アルコキシ基、チエニルＣ１−６アルコキシ基、ピリジルＣ１−６アルコキシ基、フェノキシＣ１−６アルキル基およびピリジルオキシＣ１−６アルキル基；
［置換基群ｇ−２］
Ｃ１−８アルキル基、Ｃ２−８アルケニル基、Ｃ２−８アルキニル基、Ｃ３−８シクロアルキルＣ１−６アルキル基、フェニルＣ１−６アルキル基、フリルＣ１−６アルキル基、チエニルＣ１−６アルキル基、ベンゾフリルＣ１−６アルキル基、ベンゾチエニルＣ１−６アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、フェノキシ基、Ｃ３−８シクロアルキルＣ１−６アルコキシ基、フェニルＣ１−６アルコキシ基、フリルＣ１−６アルコキシ基、チエニルＣ１−６アルコキシ基、ピリジルＣ１−６アルコキシ基、フェノキシＣ１−６アルキル基およびピリジルオキシＣ１−６アルキル基；
ただし、前記の置換基群ｇ−２に記載の各基は、以下の置換基群ｈから選ばれる置換基を１ないし３個有する；
［置換基群ｈ］
ハロゲン原子、水酸基、シアノ基、トリフルオロメチル基、Ｃ１−６アルキル基、Ｃ１−６アルコキシ基およびＣ１−６アルキルチオ基〕

６． 式（１）において、Ｅが、置換基群ｇ−１および置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフェニル基である５．記載の農業用組成物。

７． 式（１）において、Ｅが、以下の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されたフリル基、以下の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されたチエニル基、以下の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されたピロリル基または以下の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されたフェニル基である１．記載の農業用組成物。
〔［置換基群ｉ−１］
ハロゲン原子、Ｃ１−８アルキル基、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、Ｃ６−１０アリールオキシ基、Ｃ６−１０アリールＣ１−６アルコキシ基、（Ｃ１−Ｃ２アルコキシ）Ｃ２−Ｃ５アルコキシ基〕

８． 式（１）において、Ｅが、置換基群ｉ−１から選ばれる少なくとも１種の基で置換されたフェニル基である７．記載の農業用組成物。

９． 式（１）において、Ｅが、以下の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されたフリル基、以下の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されたチエニル基、以下の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されたピロリル基または以下の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されたフェニル基である１．に記載の農業用組成物。
〔［置換基群ｊ−１］
ハロゲン原子、Ｃ１−８アルコキシ基、Ｃ３−８アルケニルオキシ基、Ｃ３−８アルキニルオキシ基、（Ｃ１−Ｃ２アルコキシ）Ｃ２−Ｃ５アルコキシ基〕

１０． 式（１）において、Ｅが、置換基群ｊ−１から選ばれる少なくとも１種の基で置換されたフェニル基である９．記載の農業用組成物。

１１． 式（１）において、ＡがＡ¹である１．〜１０．のいずれか１項記載の農業用組成物。

１２． 式（１）において、ＡがＡ³である１．〜１０．のいずれか１項記載の農業用組成物。

１３． 式（１）において、ＡがＡ¹であり、ｐが０である１．〜１０．のいずれか１項記載の農業用組成物。

１４． 式（１）において、ＡがＡ³であり、ｒが０である１．〜１０．のいずれか１項記載の農業用組成物。

１５． 式（１）において、ｎが１または２である１．〜１４．のいずれか１項記載の農業用組成物。

１６． 植物病原菌が植物病原性糸状菌である１．〜１５．のいずれか１項記載の農業用組成物。

１７． １．〜１５．のいずれか１項記載の農業用組成物の有効量を有用作物に施用する、植物病原菌による病害を防除又は予防する方法。

１８． 施用方法が、茎葉散布、土壌処理または種子消毒である１７．記載の方法。   As a result of intensive studies, the present inventor has found that the ether compound represented by the formula (1) has excellent efficacy for controlling or preventing plant diseases caused by phytopathogenic fungi, and has reached the present invention.
  That is, the present invention
(1) To control or prevent plant diseases caused by plant pathogens,
Formula (1)

[Where,
A is the following A¹, A²Or A^Three

(In the formula
p represents any integer from 0 to 6;
q represents any integer from 0 to 5,
r represents any integer from 0 to 4;
R¹Represents a halogen atom, a C1-C4 alkyl group or a cyano group,
R²Represents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group or a cyano group,
R^ThreeRepresents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group or a cyano group.
However, if p is an integer from 2 to 6, each R¹Are the same as or different from each other, and when q is an integer from 2 to 5,²Are the same or different from each other, and when r is an integer from 2 to 4, each R^ThreeAre the same or different from each other. )
n represents any integer from 1 to 4,
E represents furyl, thienyl, pyrrolyl, tetrazolyl, thiazolyl, pyrazolyl
Group or phenyl group,
Any group represented by E may be substituted with at least one group selected from the following substituent group a-1 and substituent group a-2;
[Substituent group a-1]
Halogen atom, amino group, hydroxyl group, mercapto group, cyano group, formyl group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group , 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, C6-10 aryl C2-6 alkenyl Group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5- 10-membered heterocyclic oxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio group, C3-8 cyclo Alkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenylamino group, mono-C2 -6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 aryl C1-6 alkylamino Group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N- C2-6 alkenyl-N-C1-6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6 -10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 Alkylamino group, N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, C1-6 alkylcarbonyl group, C6-10 arylcarbonyl group, C1-6 alkoxycarbonyl group, C1-6 An alkylsulfonyl group, a C1-6 alkylsulfinyl group, a formula —C (═N—R;^a1) R^a2A group represented by the formula:^a1Means a hydroxyl group or a C1-6 alkoxy group; R^a2Means a hydrogen atom or a C1-6 alkyl group. ), A C6-10 aryloxy C1-6 alkyl group, a 5-10 membered heterocyclic oxy C1-6 alkyl group and a C1-3 trialkylsilyl C2-8 alkynyl group;
[Substituent group a-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1 -8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio Group, C3-8 cycloalkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenyl Amino group, mono-C2-6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 Aryl C1-6 alkylamino group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1-6 alkylamino group, N- C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6 10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkyl An amino group, an N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxyC1-6 alkyl group;
However, each group described in the substituent group a-2 has 1 to 3 substituents selected from the following substituent group b-1;
[Substituent group b-1]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group , C1-6 alkoxy group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-8 alkylthio group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoro One mono-C6-10 arylamino group and one amino group which may have one methoxy group, mono-C1-6 alkylamino group, di-C1-6 alkylamino group, amino group or aminosulfonyl group N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group which may have]
Or a salt thereof or a hydrate thereof (hereinafter also referred to as the present compound), an agricultural composition (hereinafter also referred to as the agricultural composition of the present invention),
(2) A method for controlling or preventing plant diseases caused by phytopathogenic fungi, wherein an effective amount of the agricultural composition of the present invention is applied to useful crops;
(3) Use of the present compound or a salt thereof or a hydrate thereof for producing the agricultural composition of the present invention is provided.
  More specifically, the present invention relates to the following 1. -18. It is as follows.
1. To control plant diseases caused by plant pathogens (excluding Aspergillus),
Formula (1)

[Where,
A is the following A¹, A²Or A^Three

(In the formula
p represents any integer from 0 to 6;
q represents any integer from 0 to 5,
r represents any integer from 0 to 4;
R¹Represents a halogen atom, a C1-C4 alkyl group or a cyano group,
R²Represents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group or a cyano group,
R^ThreeRepresents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group or a cyano group.
However, if p is an integer from 2 to 6, each R¹Are the same as or different from each other, and when q is an integer from 2 to 5,²Are the same or different from each other, and when r is an integer from 2 to 4, each R^ThreeAre the same or different from each other. )
n represents any integer from 1 to 4,
E represents furyl, thienyl, pyrrolyl, tetrazolyl, thiazolyl, pyrazolyl
Group or phenyl group,
Any group represented by E may be substituted with at least one group selected from the following substituent group a-1 and substituent group a-2;
[Substituent group a-1]
Halogen atom, amino group, hydroxyl group, mercapto group, cyano group, formyl group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group , 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, C6-10 aryl C2-6 alkenyl Group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5- 10-membered ring oxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5 10-membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl C1- 6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenylamino group, mono-C2-6 alkynyl Amino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 aryl C1-6 alkylamino group, mono -5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2- Alkenyl-N-C1-6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6-10 aryl -N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, C1-6 alkylcarbonyl group, C6-10 arylcarbonyl group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group , C1-6 alkylsulfinyl group, formula -C (= NR^a1) R^a2A group represented by the formula:^a1Means a hydroxyl group or a C1-6 alkoxy group; R^a2Means a hydrogen atom or a C1-6 alkyl group. ), A C6-10 aryloxy C1-6 alkyl group, a 5-10 membered heterocyclic oxy C1-6 alkyl group and a C1-C3 trialkylsilyl C2-8 alkynyl group;
[Substituent group a-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio Group, C3-8 cycloalkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenyl Amino group, mono-C2-6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 Aryl C1-6 alkylamino group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1-6 alkylamino group, N- C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6 10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkyl An amino group, an N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxyC1-6 alkyl group;
However, each group described in the substituent group a-2 has 1 to 3 substituents selected from the following substituent group b-1;
[Substituent group b-1]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group , C1-6 alkoxy group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-8 alkylthio group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoro One mono-C6-10 arylamino group and one amino group which may have one methoxy group, mono-C1-6 alkylamino group, di-C1-6 alkylamino group, amino group or aminosulfonyl group N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group which may have]
The agricultural composition containing the ether compound represented by these, its salt, or those hydrates.

2. In formula (1), E is a furyl group substituted with at least one group selected from substituent group a-1 and substituent group a-2, substituent group a-1 and substituent group a-2. A thienyl group substituted with at least one group selected from: a pyrrolyl group substituted with at least one group selected from substituent group a-1 and substituent group a-2; or substituent group a-1. 1. A phenyl group substituted with at least one group selected from substituent group a-2. The agricultural composition as described.

3. In the formula (1), E is a furyl group substituted with at least one group selected from the following substituent group a-3 and substituent group a-4, the following substituent group a-3 and substituent Thienyl group substituted with at least one group selected from group a-4, pyrrolyl group substituted with at least one group selected from the following a-3 and substituent group a-4, or the following substituents 1. a phenyl group substituted by at least one group selected from group a-3 and substituent group a-4; The agricultural composition as described.
[Substituent group a-3]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered hetero Cyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1- 8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, 5-10 membered heterocyclic ring C1 -6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 Loalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino Group, mono-C2-6 alkenylamino group, mono-C2-6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkyl Amino group, mono-C6-10 aryl C1-6 alkylamino group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1 -6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl -N-C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6 -10 aryl C1-6 alkyl-N-C1-6 alkylamino group, N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, C1-6 alkylcarbonyl group, C1-6 alkoxy A carbonyl group, a C1-6 alkylsulfonyl group, a formula -C (= NR^a1) R^a2A group represented by the formula:^a1Means a hydroxyl group or a C1-6 alkoxy group; R^a2Means a hydrogen atom or a C1-6 alkyl group. ), A C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxy C1-6 alkyl group;
[Substituent group a-4]
C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C6-10 aryl C1 -6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 Alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl C1-6 alkylthio C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenylamino group, mono-C2-6 alkynylamino group, Mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 aryl C1-6 alkylamino group, mono-5- 10-membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1-6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino Group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group, N-5-10 membered heterocycle C1-6 An alkyl-N-C1-6 alkylamino group, a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxyC1-6 alkyl group;
However, each group described in the substituent group a-4 has 1 to 3 substituents selected from the following substituent group b-2;
[Substituent group b-2]
Hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, 5-10 membered heterocyclic group, C1-6 alkoxy group, C6- 10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoromethoxy group, mono-C1-6 alkylamino group, di-C1 -6 mono-C6-10 arylamino group which may have one alkylamino group, amino group or aminosulfonyl group and N-C6-10 aryl C1-6 which may have one amino group Alkyl-N-C1-6 alkylamino group]

4). In the formula (1), E represents a furyl group that may have one or two substituents selected from the following substituent group e-1 and substituent group e-2, and the following substituent group e-1 And a thienyl group which may have one or two substituents selected from the substituent group e-2, one or two substituents selected from the following substituent group e-1 and substituent group e-2 1. a pyrrolyl group which may have, or a phenyl group which may have one or two substituents selected from the following substituent group e-1 and substituent group e-2. The agricultural composition as described.
[[Substituent group e-1]
Halogen atom, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C6-10 aryl group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6 -10 aryl C1-6 alkyl group, C6-10 aryl C2-6 alkenyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C6-10 arylthio group, C6-10 Aryl C1-6 alkylthio group, mono-C6-10 arylamino group, mono-C6-10 aryl C1- Alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group, C6-10 aryloxy C1-6 alkyl group And a 5-10 membered heterocyclic oxy C1-6 alkyl group;
[Substituent group e-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C6-10 aryl group, C3-8 cycloalkyl C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, 5-10 membered hetero Ring C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1 -6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C6-10 arylthio group, C6-10 aryl C1-6 alkylthio group, mono-C6-10 arylamino group, mono-C6-10 aryl C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C6-10 aryl C1 6 alkyl -N-C1-6 alkylamino group, C6-10 aryloxy C1-6 alkyl group and 5-10 membered heterocyclic oxy C1-6 alkyl group;
However, each group described in the substituent group e-2 has 1 to 3 substituents selected from the following substituent group f;
[Substituent group f]
Halogen atom, hydroxyl group, cyano group, amino group, nitro group, C3-8 cycloalkyl group, C1-6 alkoxy group, C1-6 alkylthio group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1 -6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, mono-C6-10 arylamino group, trifluoromethyl group, trifluoromethoxy group and C1-6 alkyl group]

5. In the formula (1), E represents a furyl group optionally having 1 or 2 substituents selected from the following substituent group g-1 and substituent group g-2, and the following substituent group g- 1 or a thienyl group optionally having 1 or 2 substituents selected from substituent group g-2, 1 or a substituent selected from substituent group g-1 and substituent group g-2 below. 1. a pyrrolyl group which may have two or a phenyl group which may have one or two substituents selected from the following substituent group g-1 and substituent group g-2. The agricultural composition as described.
[[Substituent group g-1]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl C1-6 alkyl group, phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, Benzofuryl C1-6 alkyl group, benzothienyl C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, phenoxy group, C3-8 cycloalkyl C1-6 alkoxy group, phenyl A C1-6 alkoxy group, a furyl C1-6 alkoxy group, a thienyl C1-6 alkoxy group, a pyridyl C1-6 alkoxy group, a phenoxy C1-6 alkyl group and a pyridyloxy C1-6 alkyl group;
[Substituent group g-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl C1-6 alkyl group, phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, Benzofuryl C1-6 alkyl group, benzothienyl C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, phenoxy group, C3-8 cycloalkyl C1-6 alkoxy group, phenyl A C1-6 alkoxy group, a furyl C1-6 alkoxy group, a thienyl C1-6 alkoxy group, a pyridyl C1-6 alkoxy group, a phenoxy C1-6 alkyl group and a pyridyloxy C1-6 alkyl group;
However, each group described in the substituent group g-2 has 1 to 3 substituents selected from the following substituent group h;
[Substituent group h]
Halogen atom, hydroxyl group, cyano group, trifluoromethyl group, C1-6 alkyl group, C1-6 alkoxy group, and C1-6 alkylthio group]

6). In formula (1), E is a phenyl group which may have one or two substituents selected from substituent group g-1 and substituent group g-2. The agricultural composition as described.

7). In the formula (1), E is substituted with at least one group selected from the following substituent group i-1 and a furyl group substituted with at least one group selected from the following substituent group i-1. A thienyl group, a pyrrolyl group substituted with at least one group selected from the following substituent group i-1, or a phenyl group substituted with at least one group selected from the following substituent group i-1 1. The agricultural composition as described.
[[Substituent group i-1]
A halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C3-8 alkenyloxy group, a C3-8 alkynyloxy group, a C6-10 aryloxy group, a C6-10 aryl C1-6 alkoxy group, (C1-C2 Alkoxy) C2-C5 alkoxy group]

8). In formula (1), E is a phenyl group substituted with at least one group selected from substituent group i-1. The agricultural composition as described.

9. In the formula (1), E is substituted with at least one group selected from the following substituent group j-1 and a furyl group substituted with at least one group selected from the following substituent group j-1. A thienyl group, a pyrrolyl group substituted with at least one group selected from the following substituent group j-1, or a phenyl group substituted with at least one group selected from the following substituent group j-1 1. Agricultural composition according to 1.
[[Substituent group j-1]
Halogen atom, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, (C1-C2 alkoxy) C2-C5 alkoxy group]

10. 8. In formula (1), E is a phenyl group substituted with at least one group selected from substituent group j-1. The agricultural composition as described.

11. In Formula (1), A is A¹1. -10. The agricultural composition according to any one of the above.

12 In Formula (1), A is A^Three1. -10. The agricultural composition according to any one of the above.

13. In Formula (1), A is A¹And p is 0. -10. The agricultural composition according to any one of the above.

14 In Formula (1), A is A^ThreeAnd r is 0. -10. The agricultural composition according to any one of the above.

15. In formula (1), n is 1 or 2 -14. The agricultural composition according to any one of the above.

16. 1. Plant pathogenic fungi are phytopathogenic fungi -15. The agricultural composition according to any one of the above.

17. 1. -15. A method for controlling or preventing diseases caused by phytopathogenic fungi, wherein an effective amount of the agricultural composition according to any one of the above is applied to useful crops.

18. 16. Application method is foliage application, soil treatment or seed disinfection. The method described.

  According to the present invention, plant diseases caused by plant pathogens can be controlled or prevented.

p is an integer from 0 to 6, and the case where p is 0 is preferable.
q is an integer from 0 to 5, and a case where q is 0 is preferable.
r is an integer from 0 to 4, and a case where r is 0 is preferable.

n is an integer from 1 to 4, and the case where n is 1 or 2 is preferable.

Examples of the halogen atom represented by R ¹ , R ² and R ³ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom,
Examples of the C1-C4 alkyl group include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.
Examples of the C1-C4 alkoxy group represented by R ² and R ³ include a methoxy group, an ethoxy group, a 1-methylethoxy group, a 1,1-dimethylethoxy group, a propoxy group, a 1-methylpropoxy group, and a 2-methylpropoxy group. And butoxy groups, etc.
Preferred examples of the group represented by R ¹ , R ² and R ³ include a fluorine atom.

E in the formula (1) representing this compound is a furyl group optionally substituted with at least one group selected from the following substituent group a-1 and substituent group a-2, and the following substituents A thienyl group optionally substituted with at least one group selected from group a-1 and substituent group a-2, at least one selected from the following substituent group a-1 and substituent group a-2 A pyrrolyl group which may be substituted with the following groups or a tetrazolyl group which may be substituted with at least one group selected from the following substituent group a-1 and substituent group a-2, and the following substituent group a thiazolyl group optionally substituted with at least one group selected from a-1 and substituent group a-2, at least one selected from the following substituent group a-1 and substituent group a-2 A pyrazolyl group optionally substituted by a group, Is at least one phenyl group optionally substituted with a group selected from the substituent group a-1 and substituent group a-2 below.
[Substituent group a-1]
Halogen atom, amino group, hydroxyl group, mercapto group, cyano group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5- 10-membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 al Nylthio group, C2-8 alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic ring C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenylamino group, mono-C2-6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino Group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 aryl C1-6 alkylamino group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkyl Amino group, N—C 2-6 alkenyl-N—C 1-6 alkylamino group, N—C 2-6 alkynyl-N—C -6 alkylamino group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl -N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group, N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino A group, a C1-6 alkylcarbonyl group, a C1-6 alkoxycarbonyl group, a C1-6 alkylsulfonyl group, a group represented by the formula —C (═N—R ^a1 ) R ^a2 (wherein R ^a1 is a hydroxyl group or means a C1-6 alkoxy group;. R ^a2 is to mean a hydrogen atom or a C1-6 alkyl group), C6-10 aryloxy C1-6 alkyl group and 5-10 membered heterocyclic oxy 1-6 alkyl group;
[Substituent group a-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenyl Thio group, C2-8 alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl 1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenylamino group, mono-C2- 6-alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 aryl C1-6 alkylamino group Mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1-6 alkylamino group, N-C2-6 alkynyl-N- C1-6 alkylamino group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 Alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group, N-5-10 member A heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxy C1-6 alkyl group;
However, each group described in the substituent group a-2 has 1 to 3 substituents selected from the following substituent group b-1;
[Substituent group b-1]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group , C1-6 alkoxy group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoromethoxy group, mono-C1 It may have one -6 alkylamino group, di-C1-6 alkylamino group, one amino group or one aminosulfonyl group, and one mono-C6-10 arylamino group and one amino group. N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group]

Preferably, E is a furyl group substituted with at least one group selected from the substituent group a-1 and the substituent group a-2, the substituent group a-1 and the substituent group a-1. A thienyl group substituted with at least one group selected from substituent group a-2, substituted with at least one group selected from substituent group a-1 and substituent group a-2; Examples thereof include a pyrrolyl group or a phenyl group substituted with at least one group selected from the substituent group a-1 and the substituent group a-2.

Preferably, as E, any group of 2-furyl group, 2-thienyl group, pyrrolyl group, and phenyl group,
[1 to 3 selected from the group consisting of fluorine atom, chlorine atom, (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group and C1-6 alkyl group C1-8 alkyl group (optionally substituted with 1 group), (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group and C1-6 alkyl) A C2-8 alkenyl group (which may be substituted with 1 to 3 groups selected from the group consisting of groups), (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 A C2-8 alkynyl group (optionally substituted with 1 to 3 groups selected from the group consisting of a membered heterocyclic oxy group and a C1-6 alkyl group), (halogen atom, C3 A phenyl group (which may be substituted with 1 to 3 groups selected from the group consisting of a 5 cycloalkyl group, a C1-6 alkoxy group and a C1-6 alkyl group), a halogen atom and a C1-6 alkyl group; A C3-5 cycloalkyl C1-6 alkyl group (which may be substituted with 1 to 3 groups selected from the group), 1 to 3 groups selected from the group consisting of a halogen atom and a C1-6 alkyl group; A C3-5 cycloalkylidene C1-6 alkyl group, which may be substituted with a halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1- A phenyl C1-6 alkyl group (optionally substituted with 1 to 3 groups selected from the group consisting of 6 alkyl groups), (halogen atom, C3-5 cyclo) (Optionally substituted with 1 to 3 groups selected from the group consisting of an alkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group, and a C1-6 alkyl group) phenyl C2-6 An alkenyl group (1 to 3 groups selected from the group consisting of a halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group) Optionally substituted) 5-6 membered heterocyclic C1-6 alkyl group (optionally substituted with 1 to 3 groups selected from the group consisting of halogen atoms and C1-6 alkyl groups) C1- 8 alkoxy groups, C 3-8 alkenyloxy groups (which may be substituted with 1 to 3 groups selected from the group consisting of halogen atoms and C 1-6 alkyl groups), (halogen atoms) And a C3-8 alkynyloxy group (which may be substituted with 1 to 3 groups selected from the group consisting of C1-6 alkyl groups), (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, A phenoxy group, which may be substituted with 1 to 3 groups selected from the group consisting of a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group) A good C3-6 cycloalkyl C1-6 alkoxy group (from the group consisting of a halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group) A phenyl C1-6 alkoxy group (which may be substituted with 1 to 3 groups selected), (halogen atom, C3-5 cycloalkyl group, C1-6 alcohol) (Optionally substituted with 1 to 3 groups selected from the group consisting of a cis group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group) 5-6 membered heterocyclic C1-6 alkoxy A group (which may be substituted with 1 to 3 groups selected from the group consisting of a halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, a phenoxy group and a 5-6-membered heterocyclic oxy group) A phenoxy C1-6 alkyl group, and a 5-6 membered hetero (optionally substituted with 1 to 3 groups selected from the group consisting of a halogen atom, a C3-5 cycloalkyl group and a C1-6 alkoxy group) A group optionally substituted with 1 or 2 groups selected from the group consisting of a ring oxy C1-6 alkyl group] (preferably a group optionally substituted). .

Particularly preferably, E is a group selected from a 2-furyl group, a 2-thienyl group, and a phenyl group [a fluorine atom, a chlorine atom, a (halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, A C1-8 alkyl group (which may be substituted with 1 to 3 groups selected from the group consisting of a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group), (halogen atom, C3-5) (Optionally substituted with 1 to 3 groups selected from the group consisting of a cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group) C2-8 1 selected from the group consisting of an alkenyl group, a (halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group, and a C1-6 alkyl group 1 to 3 selected from the group consisting of a C2-8 alkynyl group (optionally substituted with 3 groups), a halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, and a C1-6 alkyl group A phenyl group (which may be substituted with 1 group), a C3-5 cycloalkyl C1- (which may be substituted with 1 to 3 groups selected from the group consisting of a halogen atom and a C1-6 alkyl group). A 6 alkyl group (which may be substituted with 1 to 3 groups selected from the group consisting of a halogen atom and a C1-6 alkyl group), a C3-5 cycloalkylidene C1-6 alkyl group, (a halogen atom, C3- 1 to 3 groups selected from the group consisting of a 5-cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group. A group consisting of a phenyl C1-6 alkyl group (which may be substituted), a halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group. Phenyl C2-6 alkenyl group (which may be substituted with 1 to 3 groups selected from the above), (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocycle) A 5-6 membered heterocyclic C1-6 alkyl group (which may be substituted with 1 to 3 groups selected from the group consisting of an oxy group and a C1-6 alkyl group) (from a halogen atom and a C1-6 alkyl group) A C1-8 alkoxy group which may be substituted with 1 to 3 groups selected from the group consisting of: 1 selected from the group consisting of a halogen atom and a C1-6 alkyl group C3-8 alkenyloxy group (which may be substituted with up to 3 groups), C3 (which may be substituted with 1 to 3 groups selected from the group consisting of halogen atoms and C1-6 alkyl groups) -8 alkynyloxy group, 1 to 3 selected from the group consisting of a halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group, and a C1-6 alkyl group A phenoxy group which may be substituted with a group, a C3-6 cycloalkyl C1-6 alkoxy group which may be substituted with 1 to 3 halogen atoms, (a halogen atom, a C3-5 cycloalkyl group, C1-6 alkoxy) Optionally substituted with 1 to 3 groups selected from the group consisting of a group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group) 1-6 alkoxy groups, 1 to 3 selected from the group consisting of a halogen atom, a C3-5 cycloalkyl group, a C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group 5-6-membered heterocyclic C1-6 alkoxy group, which may be substituted with a group of (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, and 5-6-membered heterocyclic oxy group Selected from the group consisting of a phenoxy C1-6 alkyl group (which may be substituted with 1 to 3 groups selected from the group consisting of) and (a halogen atom, a C3-5 cycloalkyl group and a C1-6 alkoxy group). And optionally substituted with 1 or 2 groups selected from the group consisting of 5-6 membered heterocyclic oxy C1-6 alkyl groups. (Among them preferably, group which may optionally be monosubstituted) which may group optionally or,
N (nitrogen atom) may be substituted with 1 to 3 by [(halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group, C1-6 alkyl group]. ) C1-6 alkyl group, (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group, C1-6 alkyl group may be substituted 1 to 3) ) C2-8 alkenyl group (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group, C1-6 alkyl group may be substituted 1 to 3) ) C2-8 alkynyl group, (optionally substituted by 1 to 3 with a halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, C1-6 alkyl group) phenyl group (halogen atom) C1-6 alkyl group may be substituted by 1 to 3) C3-5 cycloalkyl C1-6 alkyl group (halogen atom, C1-6 alkyl group may be substituted by 1 to 3) C3-5 cyclo Alkylidene C1-6 alkyl group, (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group, C1-6 alkyl group may be substituted by 1 to 3) ) Phenyl C1-6 alkyl group, (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group, C1-6 alkyl group may be substituted by 1 to 3) Good) 5-6 membered heterocyclic C1-6 alkyl group, (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group, 1 A phenoxy C1-6 alkyl group (which may be substituted by 1 to 3) or a 5-6 membered heterocyclic oxy C1- (which may be substituted 1 to 3 by a halogen atom, a C3-5 cycloalkyl group or a C1-6 alkoxy group) 6-alkyl group] may be substituted 3-pyrrolyl group.

Preferably, E is a furyl group substituted with at least one group selected from the following substituent group a-3 and substituent group a-4, the following substituent group a-3 and substituent group a Thienyl group substituted with at least one group selected from -4, pyrrolyl group substituted with at least one group selected from the following a-3 and substituent group a-4, or the following substituent group a -3 and a phenyl group substituted with at least one group selected from substituent group a-4.
[Substituent group a-3]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered hetero Cyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1- 8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, 5-10 membered heterocyclic ring C1 -6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 Loalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino Group, mono-C2-6 alkenylamino group, mono-C2-6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkyl Amino group, mono-C6-10 aryl C1-6 alkylamino group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1 -6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl -N-C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6 -10 aryl C1-6 alkyl-N-C1-6 alkylamino group, N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, C1-6 alkylcarbonyl group, C1-6 alkoxy A carbonyl group, a C1-6 alkylsulfonyl group, a group represented by the formula —C (═N—R ^a1 ) R ^a2 (wherein R ^a1 represents a hydroxyl group or a C1-6 alkoxy group; R ^a2 represents A hydrogen atom or a C1-6 alkyl group), a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxy C1-6 alkyl group;
[Substituent group a-4]
C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C6-10 aryl C1 -6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 Alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl C1-6 alkylthio C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenylamino group, mono-C2-6 alkynylamino group, Mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 aryl C1-6 alkylamino group, mono-5- 10-membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1-6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino Group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group, N-5-10 membered heterocycle C1-6 An alkyl-N-C1-6 alkylamino group, a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxy C1-6 alkyl group;
However, each group described in the substituent group a-4 has 1 to 3 substituents selected from the following substituent group b-2;
[Substituent group b-2]
Hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, 5-10 membered heterocyclic group, C1-6 alkoxy group, C6- 10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoromethoxy group, mono-C1-6 alkylamino group, di-C1 -6 mono-C6-10 arylamino group which may have one alkylamino group, amino group or aminosulfonyl group and N-C6-10 aryl C1-6 which may have one amino group Alkyl-N-C1-6 alkylamino group]

Preferably, E is a furyl group which may have one or two substituents selected from the following substituent group e-1 and substituent group e-2, the following substituent group e-1 and substituents A thienyl group optionally having 1 or 2 substituents selected from the group e-2, 1 or 2 substituents selected from the following substituent group e-1 and substituent group e-2 And a phenyl group which may have one or two substituents selected from the following pyrrolyl group or the following substituent group e-1 and substituent group e-2.
[[Substituent group e-1]
Halogen atom, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C6-10 aryl group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6 -10 aryl C1-6 alkyl group, C6-10 aryl C2-6 alkenyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C6-10 arylthio group, C6-10 Aryl C1-6 alkylthio group, mono-C6-10 arylamino group, mono-C6-10 aryl C1- Alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group, C6-10 aryloxy C1-6 alkyl group And a 5-10 membered heterocyclic oxy C1-6 alkyl group;
[Substituent group e-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C6-10 aryl group, C3-8 cycloalkyl C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, 5-10 membered hetero Ring C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1 -6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C6-10 arylthio group, C6-10 aryl C1-6 alkylthio group, mono-C6-10 arylamino group, mono-C6-10 aryl C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C6-10 aryl C1 6 alkyl -N-C1-6 alkylamino group, C6-10 aryloxy C1-6 alkyl group and 5-10 membered heterocyclic oxy C1-6 alkyl group;
However, each group described in the substituent group e-2 has 1 to 3 substituents selected from the following substituent group f;
[Substituent group f]
Halogen atom, hydroxyl group, cyano group, amino group, nitro group, C3-8 cycloalkyl group, C1-6 alkoxy group, C1-6 alkylthio group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1 -6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, mono-C6-10 arylamino group, trifluoromethyl group, trifluoromethoxy group and C1-6 alkyl group]

Preferably, as E, a furyl group optionally having 1 or 2 substituents selected from the following substituent group g-1 and substituent group g-2, the following substituent group g-1 and Thienyl group optionally having 1 or 2 substituents selected from substituent group g-2, 1 or 2 substituents selected from substituent group g-1 and substituent group g-2 below Examples thereof include a pyrrolyl group which may have, or a phenyl group which may have one or two substituents selected from the following substituent group g-1 and substituent group g-2.
[[Substituent group g-1]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl C1-6 alkyl group, phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, Benzofuryl C1-6 alkyl group, benzothienyl C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, phenoxy group, C3-8 cycloalkyl C1-6 alkoxy group, phenyl A C1-6 alkoxy group, a furyl C1-6 alkoxy group, a thienyl C1-6 alkoxy group, a pyridyl C1-6 alkoxy group, a phenoxy C1-6 alkyl group and a pyridyloxy C1-6 alkyl group;
[Substituent group g-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl C1-6 alkyl group, phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, Benzofuryl C1-6 alkyl group, benzothienyl C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, phenoxy group, C3-8 cycloalkyl C1-6 alkoxy group, phenyl A C1-6 alkoxy group, a furyl C1-6 alkoxy group, a thienyl C1-6 alkoxy group, a pyridyl C1-6 alkoxy group, a phenoxy C1-6 alkyl group and a pyridyloxy C1-6 alkyl group;
However, each group described in the substituent group g-2 has 1 to 3 substituents selected from the following substituent group h;
[Substituent group h]
Halogen atom, hydroxyl group, cyano group, trifluoromethyl group, C1-6 alkyl group, C1-6 alkoxy group and C1-6 alkylthio group]

More preferably, E is a furyl group substituted with at least one group selected from the following substituent group i-1 and substituted with at least one group selected from the following substituent group i-1. A thienyl group, a pyrrolyl group substituted with at least one group selected from the following substituent group i-1, or a phenyl group substituted with at least one group selected from the following i-1. it can.
[Substituent group i-1]
A halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C3-8 alkenyloxy group, a C3-8 alkynyloxy group, a C6-10 aryloxy group, a C6-10 aryl C1-6 alkoxy group, (C1-C2 Alkoxy) C2-C5 alkoxy group

Particularly preferably, E is a furyl group substituted with at least one group selected from the following substituent group j-1, and is substituted with at least one group selected from the following substituent group j-1. A thienyl group, a pyrrolyl group substituted with at least one group selected from the following substituent group j-1 or a phenyl group substituted with at least one group selected from j-1 below. it can.
[Substituent group j-1]
Halogen atom, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, (C1-C2 alkoxy) C2-C5 alkoxy group

In the present specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and the like, and examples of the C1-8 alkyl group include a methyl group, an ethyl group, an n-propyl group, and an iso-propyl group. , N-butyl group, iso-butyl group, n-pentyl group, iso-pentyl group, n-hexyl group, 4-methylpentyl group, 3-methylpentyl group and the like. Is vinyl group, allyl group, 2-butenyl group, 3-butenyl group, 2-pentenyl group, 3-pentenyl group, prenyl group, 3-methyl-3-butenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 4-methyl-4-pentenyl group, 4-methyl-3-pentenyl group and the like can be mentioned. Examples of C2-8 alkynyl group include ethynyl group, propyl group, and the like. Pargyl group, 2-butynyl group, 3-butynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, etc. Examples of the C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. A C6-10 aryl group includes a phenyl group. , Indenyl group, naphthyl group and the like, and examples of the 5-10 membered heterocyclic group include furyl group, thienyl group, thiazolyl group, pyrazolyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, benzofuranyl group , Benzothienyl group, benzothiazolyl group, chromenyl group, isochromenyl , A thiochromenyl group, an isothiochromenyl group, and the like. Examples of the C3-8 cycloalkyl C1-6 alkyl group include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclopropylpropyl group, a cyclopropylbutyl group, and a cyclopropyl group. Pentyl group, cyclopropylhexyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclobutylpropyl group, cyclobutylbutyl group, cyclobutylpentyl group, cyclopentylethyl group, cyclopentylpropyl group, cyclopentylbutyl group, cyclohexylethyl group, cyclohexyl A propyl group etc. can be mentioned, As a C3-8 cycloalkylidene C1-6 alkyl group, a cyclopropylidenemethyl group, a cyclopropylideneethyl group, a cyclopropylidenepropyl group, cyclo Propylidenebutyl group, cyclopropylidenepentyl group, cyclopropylidenehexyl group, cyclobutylidenemethyl group, cyclobutylideneethyl group, cyclobutylidenepropyl group, cyclobutylidenebutyl group, cyclobutylidenepentyl group, cyclopentylidene Examples thereof include an ethyl group, a cyclopentylidenepropyl group, a cyclopentylidenebutyl group, a cyclohexylideneethyl group, a cyclohexylidenepropyl group, and the C6-10 aryl C1-6 alkyl group includes a benzyl group and a phenethyl group. , Phenylpropyl group, phenylbutyl group, phenylpentyl group, 2-methyl-4-phenylbutyl group, 2-methyl-5-phenylpentyl group, 3-methyl-5-phenylpentyl group, (2-naphthyl) ethyl group C6- Examples of the 10 aryl C2-6 alkenyl group include a styryl group and a phenylpropenyl group. Examples of the 5-10 membered heterocyclic C1-6 alkyl group include a furylmethyl group, a furylethyl group, a furylpropyl group, Examples include a furylbutyl group, a furylpentyl group, a furylhexyl group, a thienylmethyl group, a thienylethyl group, a thienylpropyl group, a thienylbutyl group, a thienylpentyl group, and a thienylhexyl group. Group, ethoxy group, n-propyloxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, n-pentyloxy group, iso-pentyloxy group, sec-pentyloxy group, n -Hexyloxy group, iso-hexyloxy group, sec-hexyl An oxy group, a 2,3-dimethylbutoxy group, and the like can be mentioned. As the C3-8 alkenyloxy group, an allyloxy group, a 1-methyl-2-propenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, prenyloxy group, 3-methyl-3-butenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 4-methyl-4-pentenyl An oxy group, a 4-methyl-3-pentenyloxy group, and the like can be given. Examples of the C3-8 alkynyloxy group include a propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, 3 -Pentynyloxy group, 4-pentynyloxy group, 2-hexynyloxy group, 3-hexynyl An oxy group, a 4-hexynyloxy group, a 5-hexynyloxy group, and the like can be mentioned. Examples of the C3-8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and a cycloheptyloxy group. , A cyclooctyloxy group and the like, examples of the C6-10 aryloxy group include a phenoxy group and a naphthoxy group, and examples of the C3-8 cycloalkyl C1-6 alkoxy group include a cyclopropylmethoxy group. , Cyclopropylethoxy group, cyclopropylpropoxy group, cyclopropylbutoxy group, cyclopropylpentyloxy group, cyclopropylhexyloxy group, cyclobutylmethoxy group, cyclobutylethoxy group, cyclobutylpropoxy group, cyclobuty Examples include rubutoxy group, cyclobutylpentyloxy group, cyclopentylethoxy group, cyclopentylpropoxy group, cyclopentylbutoxy group, cyclohexylethoxy group, cyclohexylpropoxy group and the like. As C6-10 aryl C1-6 alkoxy group, benzyloxy group Phenethyloxy group, phenylpropyloxy group, phenylbutyloxy group, phenylpentyloxy group, 2-methyl-4-phenylbutyloxy group, 2-methyl-5-phenylpentyloxy group, 3-methyl-5-phenylpentyl An oxy group, a (2-naphthyl) ethyloxy group, and the like can be mentioned. Examples of the 5-10 membered heterocyclic C1-6 alkoxy group include a furylmethoxy group, a furylethoxy group, a furylpropyloxy group, a furylbutyloxy group, Examples thereof include rylpentyloxy group, furylhexyloxy group, thienylmethoxy group, thienylethoxy group, thienylpropyloxy group, thienylbutyloxy group, thienylpentyloxy group, thienylhexyloxy group, etc. Is a methylthio group, ethylthio group, n-propylthio group, iso-propylthio group, n-butylthio group, iso-butylthio group, n-pentylthio group, iso-pentylthio group, n-hexylthio group, 4-methylpentylthio group, 3-methylpentylthio group etc. can be mentioned, As C2-8 alkenylthio group, allylthio group, 1-methyl-2-propenylthio group, 2-butenylthio group, 3-butenylthio group, 2-pentenylthio group Group, 3-pentenylthio group, prenylthio group , 3-methyl-3-butenylthio group, 2-hexenylthio group, 3-hexenylthio group, 4-hexenylthio group, 4-methyl-4-pentenylthio group, 4-methyl-3-pentenylthio group, etc. Examples of the C2-8 alkynylthio group include propargylthio group, 2-butynylthio group, 3-butynylthio group, 2-pentynylthio group, 3-pentynylthio group, 4-pentynylthio group, 2-hexynylthio group, and 3-hexynylthio group. Group, 4-hexynylthio group, 5-hexynylthio group and the like, and as C3-8 cycloalkylthio group, cyclopropylthio group, cyclobutylthio group, cyclopentylthio group, cyclohexylthio group, cycloheptylthio group, A cyclooctylthio group, and the like. C6-10 arylthio Examples thereof include a phenylthio group, a naphthylthio group, and the like, and examples of the C3-8 cycloalkyl C1-6 alkylthio group include a cyclopropylmethylthio group, a cyclopropylethylthio group, a cyclopropylpropylthio group, and a cyclopropylbutylthio group. , Cyclopropylpentylthio group, cyclopropylhexylthio group, cyclobutylmethylthio group, cyclobutylethylthio group, cyclobutylpropylthio group, cyclobutylbutylthio group, cyclobutylpentylthio group, cyclopentylethylthio group, cyclopentylpropylthio Group, cyclopentylbutylthio group, cyclohexylethylthio group, cyclohexylpropylthio group, and the like. Examples of the C6-10 aryl C1-6 alkylthio group include benzylthio group, phenethyl group, and the like. O group, phenylpropylthio group, phenylbutylthio group, phenylpentylthio group, 2-methyl-4-phenylbutylthio group, 2-methyl-5-phenylpentylthio group, 3-methyl-5-phenylpentylthio group, etc. Examples of the 5- to 10-membered heterocyclic C1-6 alkylthio group include a furylmethylthio group, a furylethylthio group, a furylpropylthio group, a furylbutylthio group, a furylpentylthio group, a furylhexylthio group, and a thienyl. Examples thereof include an ethylthio group, a thienylmethylthio group, a thienylpropylthio group, a thienylbutylthio group, a thienylpentylthio group, a thienylhexylthio group, and the mono-C1-6 alkylamino group includes a methylamino group, ethyl Amino group, n-propylamino group, iso-propylamino group N-butylamino group, iso-butylamino group, n-pentylamino group, iso-pentylamino group, n-hexylamino group, 4-methylpentylamino group, 3-methylpentylamino group, and the like. As mono-C2-6 alkenylamino group, allylamino group, 2-butenylamino group, 3-butenylamino group, 2-pentenylamino group, 3-pentenylamino group, prenylamino group, 3-methyl-3-butenylamino group, Examples include 2-hexenylamino group, 3-hexenylamino group, 4-hexenylamino group, 4-methyl-4-pentenylamino group, 4-methyl-3-pentenylamino group, and mono-C2-6 alkynyl. As the amino group, propargylamino group, 2-butynylamino group, 3-butynyl group amino, -Pentynylamino group, 3-pentynylamino group, 4-pentynylamino group, 2-hexynylamino group, 3-hexynylamino group, 4-hexynylamino group, 5-hexynylamino group and the like. Examples of the 8 cycloalkylamino group include a cyclopropylamino group, a cyclobutylamino group, a cyclopentylamino group, a cyclohexylamino group, a cycloheptylamino group, a cyclooctylamino group, and the like. Mono-C6-10 arylamino Examples of the group include a phenylamino group and a naphthylamino group, and examples of the mono-C3-8 cycloalkyl C1-6 alkylamino group include a cyclopropylmethylamino group, a cyclopropylethylamino group, and a cyclopropylpropylamino group. Group, cyclopropyl buty Amino group, cyclopropylpentylamino group, cyclopropylhexylamino group, cyclobutylmethylamino group, cyclobutylethylamino group, cyclobutylpropylamino group, cyclobutylbutylamino group, cyclobutylpentylamino group, cyclopentylethylamino group, Examples thereof include a cyclopentylpropylamino group, a cyclopentylbutylamino group, a cyclohexylethylamino group, a cyclohexylpropylamino group, and the like. Examples of the mono-C6-10 aryl C1-6 alkylamino group include a benzylamino group and a phenethylamino group. Phenylpropylamino group, phenylbutylamino group, phenylpentylamino group, 2-methyl-4-phenylbutylamino group, 2-methyl-5-phenylpentylamino group, 3-methyl-5-phenyl Examples thereof include a nylpentylamino group and a (2-naphthyl) ethylamino group. Examples of the mono-5-10 membered heterocyclic C1-6 alkylamino group include a furylmethylamino group, a furylethylamino group, and a furylpropylamino group. Groups, furylbutylamino groups, furylpentylamino groups, furylhexylamide groups, thienylethylamino groups, thienylmethylamino groups, thienylpropylamino groups, thienylbutylamino groups, thienylpentylamino groups, thienylhexylamino groups, etc. Examples of the di-C1-6 alkylamino group include a dimethylamino group, a methylethylamino group, a diethylamino group, a methylpropylamino group, a methylbutylamino group, and the like. N-C2-6 alkenyl-N -C1-6 alkylamino group includes N And allyl-N-methylamino group, N- (2-butenyl) -N-methylamino group, N- (3-butenyl) -N-methylamino group, and the like. N-C2-6 alkynyl-N Examples of the —C 1-6 alkylamino group include an N-methyl-N-propargylamino group, an N- (2-butynyl) -N-methylamino group, and an N- (3-butynyl) -N-methylamino group. N-C3-8 cycloalkyl-N-C1-6 alkylamino group includes N-cyclopropyl-N-methylamino group, N-cyclobutyl-N-methylamino group, N-cyclopentyl-N- A methylamino group and the like, and N-C6-10 aryl-N-C1-6 alkylamino group includes an N-methylanilino group and the like. Examples of the kill C1-6 alkyl-N-C1-6 alkylamino group include N-cyclopropylmethyl-N-methylamino group, N-cyclopropylethyl-N-methylamino group, N-cyclopropylpropyl-N-methyl. An amino group, N-cyclobutylmethyl-N-methylamino group, N-cyclobutylethyl-N-methylamino group, N-cyclobutylpropyl-N-methylamino group and the like can be mentioned. N-C6-10 As aryl C1-6 alkyl-N-C1-6 alkylamino group, N-benzyl-N-methylamino group, N-phenethyl-N-methylamino group, N-phenylpropyl-N-methylamino group, N-phenylbutyl-N-methylamino group, N-phenylpentyl-N-methylamino group and the like can be mentioned. As the ring C1-6 alkyl-N-C1-6 alkylamino group, an N-furylmethyl-N-methylamino group, an N-furylethyl-N-methylamino group, an N-furylpropyl-N-methylamino group, N-furylbutyl-N-methylamino group, N-furylpentyl-N-methylamino group, N-thienyl-N-methylamino group, N-thienylethyl-N-methylamino group, N-thienylpropyl-N-methyl Examples thereof include an amino group, N-thienylbutyl-N-methylamino group, N-thienylpentyl-N-methylamino group, and the C1-6 alkylcarbonyl group includes an acetyl group, an ethylcarbonyl group, and n-propyl. Carbonyl group, iso-propylcarbonyl group, n-butylcarbonyl group, iso-butylcarbonyl group, sec-butylcarbonyl Examples thereof include a bonyl group, an n-pentylcarbonyl group, an iso-pentylcarbonyl group, a sec-pentylcarbonyl group, an n-hexylcarbonyl group, an iso-hexylcarbonyl group, a sec-hexylcarbonyl group, and the like. Examples of the group include methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, iso-propoxycarbonyl group, n-butoxycarbonyl group, iso-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentyloxycarbonyl group, an iso-pentyloxycarbonyl group, a sec-pentyloxycarbonyl group, an n-hexyloxycarbonyl group, an iso-hexyloxycarbonyl group, a sec-hexyloxycarbonyl group, and the like. 1-6 alkylsulfonyl group, methanesulfonyl group, ethanesulfonyl group, propanesulfonyl group, butanesulfonyl group, pentane sulfonyl group, and a hexanesulfonyl group or the like, the formula ^{-C (= N-R a1)} R ^Examples of the group represented by ^a2 include a hydroxyiminomethyl group, a hydroxyiminoethyl group, a methoxyiminomethyl group, an ethoxyiminomethyl group, a methoxyiminoethyl group, and the like. C6-10 aryloxy C1-6 alkyl Examples of the group include benzyloxymethyl group, benzyloxyethyl group, benzyloxypropyl group, benzyloxybutyl group, benzyloxypentyl group, (2-naphthyl) oxymethyl group and the like, and a 5-10 membered heterocyclic ring. As an oxy C1-6 alkyl group, furyloxy Tyl group, furyloxyethyl group, furyloxypropyl group, furyloxybutyl group, furyloxypentyl group, thienyloxymethyl group, thienyloxyethyl group, thienyloxypropyl group, thienyloxybutyl group, thienyloxypentyl group, pyridyloxy Examples thereof include a methyl group, a pyridyloxyethyl group, a benzofuranyloxymethyl group, a benzothienyloxymethyl group, and the C6-10 aryl C2-6 alkenyl group includes a styryl group and a phenylpropenyl group. Examples of the 5-10 membered heterocyclic oxy group include a furyloxy group, a thienyloxy group, a pyridyloxy group, a benzofuranyloxy group, and the like, and examples of the C6-10 arylcarbonyl group include phenylcarbonyl. Group, (2-naphthyl) carbo As the C1-6 alkylsulfinyl group, a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an iso-propylsulfinyl group, an n-butylsulfinyl group, an iso-butylsulfinyl group, An n-pentylsulfinyl group, an iso-pentylsulfinyl group, an n-hexylsulfinyl group, a 4-methylpentylsulfinyl group, a 3-methylpentylsulfinyl group, and the like can be mentioned. As the C1-3 trialkylsilyl C2-8 alkynyl group Include 2-trimethylsilyl-1-ethynyl group, 3-trimethylsilyl-2-propynyl group, 4-trimethylsilyl-3-butynyl group, 5-trimethylsilyl-4-pentynyl group, 6-trimethylsilyl-5-hexynyl group and the like. Can do.

More specifically, as E, phenyl group, 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 5-phenylfuran-2-yl group, 5-phenoxyfuran-2-yl group , 5- (4-fluorophenoxy) furan-2-yl group, 5- (3-fluorophenoxy) furan-2-yl group, 5- (4-methylphenoxy) furan-2-yl group, 5- (4 -Chlorophenoxy) furan-2-yl group, 5- (3-chlorophenoxy) furan-2-yl group, 5- (3-methylphenoxy) furan-2-yl group, 5- (4-methoxyphenoxy) furan 2-yl group, 5- (3-methoxyphenoxy) furan-2-yl group, 5-benzylfuran-2-yl group, 5- (4-fluorophenyl) methylfuran-2-yl group, 5- ( 3-fluorophenyl Methylfuran-2-yl group, 5- (4-methylphenyl) methylfuran-2-yl group, 5- (4-chlorophenyl) methylfuran-2-yl group, 5- (3-chlorophenyl) methylfuran-2 -Yl group, 5- (3-methylphenyl) methylfuran-2-yl group, 5- (4-methoxyphenyl) methylfuran-2-yl group, 5- (3-methoxyphenyl) methylfuran-2-yl Group,
5-phenoxythiophen-2-yl group, 5- (4-fluorophenoxy) thiophen-2-yl group, 5- (3-fluorophenoxy) thiophen-2-yl group, 5- (2-fluorophenoxy) thiophene- 2-yl group, 5- (4-methylphenoxy) thiophen-2-yl group, 5- (4-chlorophenoxy) thiophen-2-yl group, 5- (3-chlorophenoxy) thiophen-2-yl group, 5- (3-methylphenoxy) thiophen-2-yl group, 5- (4-methoxyphenoxy) thiophen-2-yl group, 5- (3-methoxyphenoxy) thiophen-2-yl group, 5- (3- Cyanophenoxy) thiophen-2-yl group, 5-benzyloxythiophen-2-yl group, 5-benzylthiophen-2-yl group, 5- (4-fluorophenyl) Nyl) methylthiophen-2-yl group, 5- (3-fluorophenyl) methylthiophen-2-yl group, 5- (4-methylphenyl) methylthiophen-2-yl group, 5- (4-chlorophenyl) methyl Thiophen-2-yl group, 5- (3-chlorophenyl) methylthiophen-2-yl group, 5- (3-methylphenyl) methylthiophen-2-yl group, 5- (4-methoxyphenyl) methylthiophene-2 -Yl group, 5- (3-methoxyphenyl) methylthiophen-2-yl group, 5- (2-thienyl) methylthiophen-2-yl group, 5- (2-pyridyl) methylthiophen-2-yl group, 5- (2-benzofuranyl) methylthiophen-2-yl group, 5-phenoxythiophen-3-yl group, 5- (4-fluorophenoxy) thiol N-3-yl group, 5- (3-fluorophenoxy) thiophen-3-yl group, 5- (4-methylphenoxy) thiophen-3-yl group, 5- (4-chlorophenoxy) thiophen-3-yl Group, 5- (3-chlorophenoxy) thiophen-3-yl group, 5- (3-methylphenoxy) thiophen-3-yl group, 5- (4-methoxyphenoxy) thiophen-3-yl group, 5- ( 3-methoxyphenoxy) thiophen-3-yl group,
3-methylphenyl group, 3-ethylphenyl group, 3-propylphenyl group, 3-butylphenyl group, 3-pentylphenyl group, 3-hexylphenyl group, 3-heptylphenyl group, 3-isobutylphenyl group, 3- (2-isobutenyl) phenyl group, 3-cyclopentylmethylidenephenyl group, 3-biphenylyl group, 3-benzylphenyl group, 3-phenylaminophenyl group, 3- (N-phenyl-N-methylamino) phenyl group, 3 -Phenylthiophenyl group, 3-phenoxyphenyl group, 3- (2-fluorophenoxy) phenyl group, 3- (3-fluorophenoxy) phenyl group, 3- (4-fluorophenoxy) phenyl group, 3- (3 5-difluorophenoxy) phenyl group, 3- (2-chlorophenoxy) phenyl group, 3- (3-chlorophenoxy) ) Phenyl group, 3- (4-chlorophenoxy) phenyl group, 3- (2-methylphenoxy) phenyl group, 3- (3-methylphenoxy) phenyl group, 3- (4-methylphenoxy) phenyl group, 3- (2-methoxyphenoxy) phenyl group, 3- (3-methoxyphenoxy) phenyl group, 3- (4-methoxyphenoxy) phenyl group, 3- (2-cyanophenoxy) phenyl group, 3- (3-cyanophenoxy) A phenyl group, a 3- (4-cyanophenoxy) phenyl group,
3-benzyloxyphenyl group, 3- (2-fluorophenylmethoxy) phenyl group, 3- (3-fluorophenylmethoxy) phenyl group, 3- (4-fluorophenylmethoxy) phenyl group, 3- (3,5- Difluorophenylmethoxy) phenyl group, 3- (2-chlorophenylmethoxy) phenyl group, 3- (3-chlorophenylmethoxy) phenyl group, 3- (4-chlorophenylmethoxy) phenyl group, 3- (2-methylphenylmethoxy) phenyl Group, 3- (3-methylphenylmethoxy) phenyl group, 3- (4-methylphenylmethoxy) phenyl group, 3- (2-methoxyphenylmethoxy) phenyl group, 3- (3-methoxyphenylmethoxy) phenyl group, 3- (4-methoxyphenylmethoxy) phenyl group, 3- (2-cyanophenylmethoxy) phenyl group, 3- (3- Anophenylmethoxy) phenyl group, 3- (4-cyanophenylmethoxy) phenyl group, 3-benzylaminophenyl group, 3- (N-benzyl-N-methylamino) phenyl group, 3- (2-furylmethoxy) phenyl Group, 3- (3-furylmethoxy) phenyl group, 3- (2-thienylmethoxy) phenyl group, 3- (3-thienylmethoxy) phenyl group, 3- (2-pyridylmethoxy) phenyl group, 3- (3 -Pyridylmethoxy) phenyl group, 3- (4-pyridylmethoxy) phenyl group, 3- (2-pyridyloxy) phenyl group, 3- (3-pyridyloxy) phenyl group, 3- (4-pyridyloxy) phenyl group 3- (6-trifluoromethylpyridin-2-yloxy) phenyl group, 3- (5-trifluoromethylpyridin-2-yloxy) Phenyl group, 3- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenyl group, 3- (2-pyrazinyloxy) phenyl group, 3- (6-chloropyridazin-3-yloxy) phenyl group,
3-methoxyphenyl group, 3-ethoxyphenyl group, 3-propoxyphenyl group, 3- (2-methylethoxy) phenyl group, 3-butoxyphenyl group, 3- (2-methylbutoxy) phenyl group, 3- (3 -Methylbutoxy) phenyl group, 3-pentyloxyphenyl group, 3-hexyloxyphenyl group, 3-heptyloxyphenyl group, 3-isoprenyloxyphenyl group, 3- (2-fluoroethoxy) phenyl group, 3- ( 3-fluoropropoxy) phenyl group, 3- (4-fluorobutoxy) phenyl group, 3- (5-fluoropentyloxy) phenyl group, 3- (6-fluorohexyloxy) phenyl group, 3- (7-fluoroheptyl) Oxy) phenyl group, 3- (2-chloroethoxy) phenyl group, 3- (3-chloropropoxy) phene Group, 3- (4-chlorobutoxy) phenyl group, 3- (5-chloropentyloxy) phenyl group, 3- (6-chlorohexyloxy) phenyl group, 3- (7-chloroheptyloxy) phenyl group, 3- (2-propenyloxy) phenyl group, 3- (2-butenyloxy) phenyl group, 3- (3-butenyloxy) phenyl group, 3- (2-pentenyloxy) phenyl group, 3- (3-pentenyloxy) Phenyl group, 3- (4-pentenyloxy) phenyl group, 3- (2-hexenyloxy) phenyl group, 3- (3-hexenyloxy) phenyl group, 3- (4-hexenyloxy) phenyl group, 3- ( 5-hexenyloxy) phenyl group, 3- (2-heptenyloxy) phenyl group, 3- (3-heptenyloxy) phenyl group, 3- (4-hex Tenenyloxy) phenyl group, 3- (5-heptenyloxy) phenyl group, 3- (6-heptenyloxy) phenyl group, 3- (3-chloro-2-propenyloxy) phenyl group, 3- (3,3-dichloro-2 -Propenyloxy) phenyl group, 3- (2-methyl-2-butenyloxy) phenyl group, 3- (3-methyl-2-butenyloxy) phenyl group, 3- (2-propynyloxy) phenyl group, 3- (2 -Butynyloxy) phenyl group, 3- (3-butynyloxy) phenyl group, 3- (2-pentynyloxy) phenyl group, 3- (3-pentynyloxy) phenyl group, 3- (4-pentynyloxy) phenyl Group, 3- (2-hexynyloxy) phenyl group, 3- (3-hexynyloxy) phenyl group, 3- (4-hexynyloxy) pheny Group, 3- (5-hexynyloxy) phenyl group, 3- (2-heptynyloxy) phenyl group, 3- (3-heptynyloxy) phenyl group, 3- (4-heptynyloxy) phenyl group, 3- (5-heptynyloxy) A phenyl group, a 3- (6-heptynyloxy) phenyl group,
3- (2-methoxyethoxy) phenyl group, 3- (3-methoxypropoxy) phenyl group, 3- (4-methoxybutoxy) phenyl group, 3- (5-methoxypentyloxy) phenyl group, 3- (6- Methoxyhexyloxy) phenyl group, 3- (7-methoxyheptyloxy) phenyl group, 3- (2-ethoxyethoxy) phenyl group, 3- (3-ethoxypropoxy) phenyl group, 3- (4-ethoxybutoxy) phenyl Group, 3- (5-ethoxypentyloxy) phenyl group, 3- (6-ethoxyhexyloxy) phenyl group, 3- (7-ethoxyheptyloxy) phenyl group,
3-cyclopropylmethoxyphenyl group, 3- (2-cyclopropylethoxy) phenyl group, 3- (3-cyclopropylpropoxy) phenyl group, 3- (4-cyclopropylbutoxy) phenyl group, 3- (5-cyclo Propylpentyloxy) phenyl group, 3- (6-cyclopropylhexyloxy) phenyl group, 3- (7-cyclopropylheptyloxy) phenyl group, 3-phenoxymethylphenyl group, 3- (2-phenylethyl) phenyl group 3- (3-phenylpropyl) phenyl group, 3- (4-phenylbutyl) phenyl group, 3- (5-phenylpentyl) phenyl group, 3- (2-phenylethoxy) phenyl group, 3- (3- Phenylpropoxy) phenyl group, 3- (4-phenylbutoxy) phenyl group, 3- (5-phenylpen Aryloxy) phenyl group, (Z)-3-styrylphenyl group,
2-fluoro-3-methylphenyl group, 2-fluoro-3-ethylphenyl group, 2-fluoro-3-propylphenyl group, 2-fluoro-3-butylphenyl group, 2-fluoro-3-pentylphenyl group, 2-fluoro-3-hexylphenyl group, 2-fluoro-3-heptylphenyl group, 2-fluoro-3-isobutylphenyl group, 2-fluoro-3- (2-isobutenyl) phenyl group, 2-fluoro-3- Cyclopentylmethylidenephenyl group, 2-fluoro-3-biphenylyl group, 2-fluoro-3-benzylphenyl group, 2-fluoro-3-phenylaminophenyl group, 2-fluoro-3- (N-phenyl-N-methyl) Amino) phenyl group, 2-fluoro-3-phenylthiophenyl group, 2-fluoro-3-phenoxyphenyl group, -Fluoro-3- (2-fluorophenoxy) phenyl group, 2-fluoro-3- (3-fluorophenoxy) phenyl group, 2-fluoro-3- (4-fluorophenoxy) phenyl group, 2-fluoro-3- (3,5-difluorophenoxy) phenyl group, 2-fluoro-3- (2-chlorophenoxy) phenyl group, 2-fluoro-3- (3-chlorophenoxy) phenyl group, 2-fluoro-3- (4- Chlorophenoxy) phenyl group, 2-fluoro-3- (2-methylphenoxy) phenyl group, 2-fluoro-3- (3-methylphenoxy) phenyl group, 2-fluoro-3- (4-methylphenoxy) phenyl group 2-fluoro-3- (2-methoxyphenoxy) phenyl group, 2-fluoro-3- (3-methoxyphenoxy) phenyl group, 2-fluoro-3- (4-methoxyphenyl) Phenoxy) phenyl group, 2-fluoro-3- (2-cyanophenoxy) phenyl group, 2-fluoro-3- (3-cyanophenoxy) phenyl group, 2-fluoro-3- (4-cyanophenoxy) phenyl group,
3-benzyloxyphenyl group, 2-fluoro-3- (2-fluorophenylmethoxy) phenyl group, 2-fluoro-3- (3-fluorophenylmethoxy) phenyl group, 2-fluoro-3- (4-fluorophenyl) Methoxy) phenyl group, 2-fluoro-3- (3,5-difluorophenylmethoxy) phenyl group, 2-fluoro-3- (2-chlorophenylmethoxy) phenyl group, 2-fluoro-3- (3-chlorophenylmethoxy) Phenyl group, 2-fluoro-3- (4-chlorophenylmethoxy) phenyl group, 2-fluoro-3- (2-methylphenylmethoxy) phenyl group, 2-fluoro-3- (3-methylphenylmethoxy) phenyl group, 2-fluoro-3- (4-methylphenylmethoxy) phenyl group, 2-fluoro-3- (2-methoxyphenylmethoxy) phenyl Phenyl group, 2-fluoro-3- (3-methoxyphenylmethoxy) phenyl group, 2-fluoro-3- (4-methoxyphenylmethoxy) phenyl group, 2-fluoro-3- (2-cyanophenylmethoxy) phenyl group 2-fluoro-3- (3-cyanophenylmethoxy) phenyl group, 2-fluoro-3- (4-cyanophenylmethoxy) phenyl group, 2-fluoro-3-benzylaminophenyl group, 2-fluoro-3- (N-benzyl-N-methylamino) phenyl group, 2-fluoro-3- (2-furylmethoxy) phenyl group, 2-fluoro-3- (3-furylmethoxy) phenyl group, 2-fluoro-3- ( 2-thienylmethoxy) phenyl group, 2-fluoro-3- (3-thienylmethoxy) phenyl group, 2-fluoro-3- (2-pyridylmethoxy) phene Nyl group, 2-fluoro-3- (3-pyridylmethoxy) phenyl group, 2-fluoro-3- (4-pyridylmethoxy) phenyl group, 2-fluoro-3- (2-pyridyloxy) phenyl group, 2- Fluoro-3- (3-pyridyloxy) phenyl group, 2-fluoro-3- (4-pyridyloxy) phenyl group, 2-fluoro-3- (6-trifluoromethylpyridin-2-yloxy) phenyl group, 2 -Fluoro-3- (5-trifluoromethylpyridin-2-yloxy) phenyl group, 2-fluoro-3- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenyl group, 2-fluoro-3 -(2-pyrazinyloxy) phenyl group, 2-fluoro-3- (6-chloropyridazin-3-yloxy) phenyl group,
2-fluoro-3-methoxyphenyl group, 2-fluoro-3-ethoxyphenyl group, 2-fluoro-3-propoxyphenyl group, 2-fluoro-3- (2-methylethoxy) phenyl group, 2-fluoro-3 -Butoxyphenyl group, 2-fluoro-3- (2-methylbutoxy) phenyl group, 2-fluoro-3- (3-methylbutoxy) phenyl group, 2-fluoro-3-pentyloxyphenyl group, 2-fluoro- 3-hexyloxyphenyl group, 2-fluoro-3-heptyloxyphenyl group, 2-fluoro-3-isoprenyloxyphenyl group, 2-fluoro-3- (2-fluoroethoxy) phenyl group, 2-fluoro-3 -(3-fluoropropoxy) phenyl group, 2-fluoro-3- (4-fluorobutoxy) phenyl group, 2-fluoro 3- (5-fluoropentyloxy) phenyl group, 2-fluoro-3- (6-fluorohexyloxy) phenyl group, 2-fluoro-3- (7-fluoroheptyloxy) phenyl group, 2-fluoro-3- (2-chloroethoxy) phenyl group, 2-fluoro-3- (3-chloropropoxy) phenyl group, 2-fluoro-3- (4-chlorobutoxy) phenyl group, 2-fluoro-3- (5-chloropentyl) Oxy) phenyl group, 2-fluoro-3- (6-chlorohexyloxy) phenyl group, 2-fluoro-3- (7-chloroheptyloxy) phenyl group, 2-fluoro-3- (2-propenyloxy) phenyl Group, 2-fluoro-3- (2-butenyloxy) phenyl group, 2-fluoro-3- (3-butenyloxy) phenyl group, 2-fur Rho-3- (2-pentenyloxy) phenyl group, 2-fluoro-3- (3-pentenyloxy) phenyl group, 2-fluoro-3- (4-pentenyloxy) phenyl group, 2-fluoro-3- ( 2-hexenyloxy) phenyl group, 2-fluoro-3- (3-hexenyloxy) phenyl group, 2-fluoro-3- (4-hexenyloxy) phenyl group, 2-fluoro-3- (5-hexenyloxy) Phenyl group, 2-fluoro-3- (2-heptenyloxy) phenyl group, 2-fluoro-3- (3-heptenyloxy) phenyl group, 2-fluoro-3- (4-heptenyloxy) phenyl group, 2-fluoro-3 -(5-heptenyloxy) phenyl group, 2-fluoro-3- (6-heptenyloxy) phenyl group, 2-fluoro-3- (3-chloro (Ro-2-propenyloxy) phenyl group, 2-fluoro-3- (3,3-dichloro-2-propenyloxy) phenyl group, 2-fluoro-3- (2-methyl-2-butenyloxy) phenyl group, 2 -Fluoro-3- (3-methyl-2-butenyloxy) phenyl group, 2-fluoro-3- (2-propynyloxy) phenyl group, 2-fluoro-3- (2-butynyloxy) phenyl group, 2-fluoro- 3- (3-butynyloxy) phenyl group, 2-fluoro-3- (2-pentynyloxy) phenyl group, 2-fluoro-3- (3-pentynyloxy) phenyl group, 2-fluoro-3- (4 -Pentynyloxy) phenyl group, 2-fluoro-3- (2-hexynyloxy) phenyl group, 2-fluoro-3- (3-hexynyloxy) phenyl group, -Fluoro-3- (4-hexynyloxy) phenyl group, 2-fluoro-3- (5-hexynyloxy) phenyl group, 2-fluoro-3- (2-heptynyloxy) phenyl group, 2-fluoro-3- (3- Heptynyloxy) phenyl group, 2-fluoro-3- (4-heptynyloxy) phenyl group, 2-fluoro-3- (5-heptynyloxy) phenyl group, 2-fluoro-3- (6-heptynyloxy) phenyl group,
3- (2-methoxyethoxy) phenyl group, 2-fluoro-3- (3-methoxypropoxy) phenyl group, 2-fluoro-3- (4-methoxybutoxy) phenyl group, 2-fluoro-3- (5- Methoxypentyloxy) phenyl group, 2-fluoro-3- (6-methoxyhexyloxy) phenyl group, 2-fluoro-3- (7-methoxyheptyloxy) phenyl group, 2-fluoro-3- (2-ethoxyethoxy) ) Phenyl group, 2-fluoro-3- (3-ethoxypropoxy) phenyl group, 2-fluoro-3- (4-ethoxybutoxy) phenyl group, 2-fluoro-3- (5-ethoxypentyloxy) phenyl group, 2-fluoro-3- (6-ethoxyhexyloxy) phenyl group, 2-fluoro-3- (7-ethoxyheptyloxy) phenyl Group,
2-fluoro-3-cyclopropylmethoxyphenyl group, 2-fluoro-3- (2-cyclopropylethoxy) phenyl group, 2-fluoro-3- (3-cyclopropylpropoxy) phenyl group, 2-fluoro-3- (4-cyclopropylbutoxy) phenyl group, 2-fluoro-3- (5-cyclopropylpentyloxy) phenyl group, 2-fluoro-3- (6-cyclopropylhexyloxy) phenyl group, 2-fluoro-3- (7-cyclopropylheptyloxy) phenyl group, 2-fluoro-3-phenoxymethylphenyl group, 2-fluoro-3- (2-phenylethyl) phenyl group, 2-fluoro-3- (3-phenylpropyl) phenyl Group, 2-fluoro-3- (4-phenylbutyl) phenyl group, 2-fluoro-3- (5-phenyl) Pentyl) phenyl group, 2-fluoro-3- (2-phenylethoxy) phenyl group, 2-fluoro-3- (3-phenylpropoxy) phenyl group, 2-fluoro-3- (4-phenylbutoxy) phenyl group, 2-fluoro-3- (5-phenylpentyloxy) phenyl group, (Z) -2-fluoro-3-styrylphenyl group,
4-methylphenyl group, 4-ethylphenyl group, 4-propylphenyl group, 4-butylphenyl group, 4-pentylphenyl group, 4-hexylphenyl group, 4-heptylphenyl group, 4-isobutylphenyl group, 4- (2-isobutenyl) phenyl group, 4-cyclopentylmethylidenephenyl group, 4-biphenylyl group, 4-benzylphenyl group, 4-phenylaminophenyl group, 4- (N-phenyl-N-methylamino) phenyl group, 4 -Phenylthiophenyl group, 4-phenoxyphenyl group, 4- (2-fluorophenoxy) phenyl group, 4- (3-fluorophenoxy) phenyl group, 4- (4-fluorophenoxy) phenyl group, 4- (3 5-difluorophenoxy) phenyl group, 4- (2-chlorophenoxy) phenyl group, 4- (3-chlorophenoxy) ) Phenyl group, 4- (4-chlorophenoxy) phenyl group, 4- (2-methylphenoxy) phenyl group, 4- (3-methylphenoxy) phenyl group, 4- (4-methylphenoxy) phenyl group, 4- (2-methoxyphenoxy) phenyl group, 4- (3-methoxyphenoxy) phenyl group, 4- (4-methoxyphenoxy) phenyl group, 4- (2-cyanophenoxy) phenyl group, 4- (3-cyanophenoxy) Phenyl group, 4- (4-cyanophenoxy) phenyl group,
4-benzyloxyphenyl group, 4- (2-fluorophenylmethoxy) phenyl group, 4- (3-fluorophenylmethoxy) phenyl group, 4- (4-fluorophenylmethoxy) phenyl group, 4- (3,5- Difluorophenylmethoxy) phenyl group, 4- (2-chlorophenylmethoxy) phenyl group, 4- (3-chlorophenylmethoxy) phenyl group, 4- (4-chlorophenylmethoxy) phenyl group, 4- (2-methylphenylmethoxy) phenyl Group, 4- (3-methylphenylmethoxy) phenyl group, 4- (4-methylphenylmethoxy) phenyl group, 4- (2-methoxyphenylmethoxy) phenyl group, 4- (3-methoxyphenylmethoxy) phenyl group, 4- (4-methoxyphenylmethoxy) phenyl group, 4- (2-cyanophenylmethoxy) phenyl group, 4- (3- Ananophenylmethoxy) phenyl group, 4- (4-cyanophenylmethoxy) phenyl group, 4-benzylaminophenyl group, 4- (N-benzyl-N-methylamino) phenyl group, 4- (2-furylmethoxy) phenyl Group, 4- (3-furylmethoxy) phenyl group, 4- (2-thienylmethoxy) phenyl group, 4- (3-thienylmethoxy) phenyl group, 4- (2-pyridylmethoxy) phenyl group, 4- (3 -Pyridylmethoxy) phenyl group, 4- (4-pyridylmethoxy) phenyl group, 4- (2-pyridyloxy) phenyl group, 4- (3-pyridyloxy) phenyl group, 4- (4-pyridyloxy) phenyl group 4- (6-trifluoromethylpyridin-2-yloxy) phenyl group, 4- (5-trifluoromethylpyridin-2-yloxy) Phenyl group, 4- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenyl group, 4- (2-pyrazinyloxy) phenyl group, 4- (6-chloropyridazin-3-yloxy) phenyl group,
4-methoxyphenyl group, 4-ethoxyphenyl group, 4-propoxyphenyl group, 4- (2-methylethoxy) phenyl group, 4-butoxyphenyl group, 4- (2-methylbutoxy) phenyl group, 4- (3 -Methylbutoxy) phenyl group, 4-pentyloxyphenyl group, 4-hexyloxyphenyl group, 4-heptyloxyphenyl group, 4-isoprenyloxyphenyl group, 4- (2-fluoroethoxy) phenyl group, 4- ( 3-fluoropropoxy) phenyl group, 4- (4-fluorobutoxy) phenyl group, 4- (5-fluoropentyloxy) phenyl group, 4- (6-fluorohexyloxy) phenyl group, 4- (7-fluoroheptyl) Oxy) phenyl group, 4- (2-chloroethoxy) phenyl group, 4- (3-chloropropoxy) phene Group, 4- (4-chlorobutoxy) phenyl group, 4- (5-chloropentyloxy) phenyl group, 4- (6-chlorohexyloxy) phenyl group, 4- (7-chloroheptyloxy) phenyl group, 4- (2-propenyloxy) phenyl group, 4- (2-butenyloxy) phenyl group, 4- (3-butenyloxy) phenyl group, 4- (2-pentenyloxy) phenyl group, 4- (3-pentenyloxy) Phenyl group, 4- (4-pentenyloxy) phenyl group, 4- (2-hexenyloxy) phenyl group, 4- (3-hexenyloxy) phenyl group, 4- (4-hexenyloxy) phenyl group, 4- ( 5-hexenyloxy) phenyl group, 4- (2-heptenyloxy) phenyl group, 4- (3-heptenyloxy) phenyl group, 4- (4-hex Tenenyloxy) phenyl group, 4- (5-heptenyloxy) phenyl group, 4- (6-heptenyloxy) phenyl group, 4- (3-chloro-2-propenyloxy) phenyl group, 4- (3,3-dichloro-2 -Propenyloxy) phenyl group, 4- (2-methyl-2-butenyloxy) phenyl group, 4- (3-methyl-2-butenyloxy) phenyl group, 4- (2-propynyloxy) phenyl group, 4- (2 -Butynyloxy) phenyl group, 4- (3-butynyloxy) phenyl group, 4- (2-pentynyloxy) phenyl group, 4- (3-pentynyloxy) phenyl group, 4- (4-pentynyloxy) phenyl Group, 4- (2-hexynyloxy) phenyl group, 4- (3-hexynyloxy) phenyl group, 4- (4-hexynyloxy) pheny Group, 4- (5-hexynyloxy) phenyl group, 4- (2-heptynyloxy) phenyl group, 4- (3-heptynyloxy) phenyl group, 4- (4-heptynyloxy) phenyl group, 4- (5-heptynyloxy) A phenyl group, 4- (6-heptynyloxy) phenyl group,
4- (2-methoxyethoxy) phenyl group, 4- (3-methoxypropoxy) phenyl group, 4- (4-methoxybutoxy) phenyl group, 4- (5-methoxypentyloxy) phenyl group, 4- (6- Methoxyhexyloxy) phenyl group, 4- (7-methoxyheptyloxy) phenyl group, 4- (2-ethoxyethoxy) phenyl group, 4- (3-ethoxypropoxy) phenyl group, 4- (4-ethoxybutoxy) phenyl Group, 4- (5-ethoxypentyloxy) phenyl group, 4- (6-ethoxyhexyloxy) phenyl group, 4- (7-ethoxyheptyloxy) phenyl group,
4-cyclopropylmethoxyphenyl group, 4- (2-cyclopropylethoxy) phenyl group, 4- (3-cyclopropylpropoxy) phenyl group, 4- (4-cyclopropylbutoxy) phenyl group, 4- (5-cyclo Propylpentyloxy) phenyl group, 4- (6-cyclopropylhexyloxy) phenyl group, 4- (7-cyclopropylheptyloxy) phenyl group, 4-phenoxymethylphenyl group, 4- (2-phenylethyl) phenyl group 4- (3-phenylpropyl) phenyl group, 4- (4-phenylbutyl) phenyl group, 4- (5-phenylpentyl) phenyl group, 4- (2-phenylethoxy) phenyl group, 4- (3- Phenylpropoxy) phenyl group, 4- (4-phenylbutoxy) phenyl group, 4- (5-phenylpene) Aryloxy) phenyl group,
(Z) -4-styrylphenyl group,
2-fluoro-4-methylphenyl group, 2-fluoro-4-ethylphenyl group, 2-fluoro-4-propylphenyl group, 2-fluoro-4-butylphenyl group, 2-fluoro-4-pentylphenyl group, 2-fluoro-4-hexylphenyl group, 2-fluoro-4-heptylphenyl group, 2-fluoro-4-isobutylphenyl group, 2-fluoro-4- (2-isobutenyl) phenyl group, 2-fluoro-4- Cyclopentylmethylidenephenyl group, 2-fluoro-4-phenylphenyl group, 2-fluoro-4-benzylphenyl group, 2-fluoro-4-phenylaminophenyl group, 2-fluoro-4- (N-phenyl-N- Methylamino) phenyl group, 2-fluoro-4-phenylthiophenyl group, 2-fluoro-4-phenoxyphenyl 2-fluoro-4- (2-fluorophenoxy) phenyl group, 2-fluoro-4- (3-fluorophenoxy) phenyl group, 2-fluoro-4- (4-fluorophenoxy) phenyl group, 2-fluoro- 4- (3,5-difluorophenoxy) phenyl group, 2-fluoro-4- (2-chlorophenoxy) phenyl group, 2-fluoro-4- (3-chlorophenoxy) phenyl group, 2-fluoro-4- ( 4-chlorophenoxy) phenyl group, 2-fluoro-4- (2-methylphenoxy) phenyl group, 2-fluoro-4- (3-methylphenoxy) phenyl group, 2-fluoro-4- (4-methylphenoxy) Phenyl group, 2-fluoro-4- (2-methoxyphenoxy) phenyl group, 2-fluoro-4- (3-methoxyphenoxy) phenyl group, 2-fluoro-4- (4-methoxy) Phenoxy) phenyl group, 2-fluoro-4- (2-cyanophenoxy) phenyl group, 2-fluoro-4- (3-cyanophenoxy) phenyl group, 2-fluoro-4- (4-cyanophenoxy) phenyl group,
4-benzyloxyphenyl group, 2-fluoro-4- (2-fluorophenylmethoxy) phenyl group, 2-fluoro-4- (3-fluorophenylmethoxy) phenyl group, 2-fluoro-4- (4-fluorophenyl) Methoxy) phenyl group, 2-fluoro-4- (3,5-difluorophenylmethoxy) phenyl group, 2-fluoro-4- (2-chlorophenylmethoxy) phenyl group, 2-fluoro-4- (3-chlorophenylmethoxy) Phenyl group, 2-fluoro-4- (4-chlorophenylmethoxy) phenyl group, 2-fluoro-4- (2-methylphenylmethoxy) phenyl group, 2-fluoro-4- (3-methylphenylmethoxy) phenyl group, 2-fluoro-4- (4-methylphenylmethoxy) phenyl group, 2-fluoro-4- (2-methoxyphenylmethoxy) phenyl Phenyl group, 2-fluoro-4- (3-methoxyphenylmethoxy) phenyl group, 2-fluoro-4- (4-methoxyphenylmethoxy) phenyl group, 2-fluoro-4- (2-cyanophenylmethoxy) phenyl group 2-fluoro-4- (3-cyanophenylmethoxy) phenyl group, 2-fluoro-4- (4-cyanophenylmethoxy) phenyl group, 2-fluoro-4-benzylaminophenyl group, 2-fluoro-4- (N-benzyl-N-methylamino) phenyl group, 2-fluoro-4- (2-furylmethoxy) phenyl group, 2-fluoro-4- (3-furylmethoxy) phenyl group, 2-fluoro-4- ( 2-thienylmethoxy) phenyl group, 2-fluoro-4- (3-thienylmethoxy) phenyl group, 2-fluoro-4- (2-pyridylmethoxy) phene Nyl group, 2-fluoro-4- (3-pyridylmethoxy) phenyl group, 2-fluoro-4- (4-pyridylmethoxy) phenyl group, 2-fluoro-4- (2-pyridyloxy) phenyl group, 2- Fluoro-4- (3-pyridyloxy) phenyl group, 2-fluoro-4- (4-pyridyloxy) phenyl group, 2-fluoro-4- (6-trifluoromethylpyridin-2-yloxy) phenyl group, 2 -Fluoro-4- (5-trifluoromethylpyridin-2-yloxy) phenyl group, 2-fluoro-4- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenyl group, 2-fluoro-4 -(2-pyrazinyloxy) phenyl group, 2-fluoro-4- (6-chloropyridazin-3-yloxy) phenyl group,
2-fluoro-4-methoxyphenyl group, 2-fluoro-4-ethoxyphenyl group, 2-fluoro-4-propoxyphenyl group, 2-fluoro-4- (2-methylethoxy) phenyl group, 2-fluoro-4 -Butoxyphenyl group, 2-fluoro-4- (2-methylbutoxy) phenyl group, 2-fluoro-4- (3-methylbutoxy) phenyl group, 2-fluoro-4-pentyloxyphenyl group, 2-fluoro- 4-hexyloxyphenyl group, 2-fluoro-4-heptyloxyphenyl group, 2-fluoro-4-isoprenyloxyphenyl group, 2-fluoro-4- (2-fluoroethoxy) phenyl group, 2-fluoro-4 -(3-fluoropropoxy) phenyl group, 2-fluoro-4- (4-fluorobutoxy) phenyl group, 2-fluoro 4- (5-fluoropentyloxy) phenyl group, 2-fluoro-4- (6-fluorohexyloxy) phenyl group, 2-fluoro-4- (7-fluoroheptyloxy) phenyl group, 2-fluoro-4- (2-chloroethoxy) phenyl group, 2-fluoro-4- (3-chloropropoxy) phenyl group, 2-fluoro-4- (4-chlorobutoxy) phenyl group, 2-fluoro-4- (5-chloropentyl) Oxy) phenyl group, 2-fluoro-4- (6-chlorohexyloxy) phenyl group, 2-fluoro-4- (7-chloroheptyloxy) phenyl group, 2-fluoro-4- (2-propenyloxy) phenyl Group, 2-fluoro-4- (2-butenyloxy) phenyl group, 2-fluoro-4- (3-butenyloxy) phenyl group, 2-fur B-4- (2-pentenyloxy) phenyl group, 2-fluoro-4- (3-pentenyloxy) phenyl group, 2-fluoro-4- (4-pentenyloxy) phenyl group, 2-fluoro-4- ( 2-hexenyloxy) phenyl group, 2-fluoro-4- (3-hexenyloxy) phenyl group, 2-fluoro-4- (4-hexenyloxy) phenyl group, 2-fluoro-4- (5-hexenyloxy) Phenyl group, 2-fluoro-4- (2-heptenyloxy) phenyl group, 2-fluoro-4- (3-heptenyloxy) phenyl group, 2-fluoro-4- (4-heptenyloxy) phenyl group, 2-fluoro-4 -(5-heptenyloxy) phenyl group, 2-fluoro-4- (6-heptenyloxy) phenyl group, 2-fluoro-4- (3-chloro (Ro-2-propenyloxy) phenyl group, 2-fluoro-4- (3,3-dichloro-2-propenyloxy) phenyl group, 2-fluoro-4- (2-methyl-2-butenyloxy) phenyl group, 2 -Fluoro-4- (3-methyl-2-butenyloxy) phenyl group, 2-fluoro-4- (2-propynyloxy) phenyl group, 2-fluoro-4- (2-butynyloxy) phenyl group, 2-fluoro- 4- (3-butynyloxy) phenyl group, 2-fluoro-4- (2-pentynyloxy) phenyl group, 2-fluoro-4- (3-pentynyloxy) phenyl group, 2-fluoro-4- (4 -Pentynyloxy) phenyl group, 2-fluoro-4- (2-hexynyloxy) phenyl group, 2-fluoro-4- (3-hexynyloxy) phenyl group, -Fluoro-4- (4-hexynyloxy) phenyl group, 2-fluoro-4- (5-hexynyloxy) phenyl group, 2-fluoro-4- (2-heptynyloxy) phenyl group, 2-fluoro-4- (3- Heptynyloxy) phenyl group, 2-fluoro-4- (4-heptynyloxy) phenyl group, 2-fluoro-4- (5-heptynyloxy) phenyl group, 2-fluoro-4- (6-heptynyloxy) phenyl group,
4- (2-methoxyethoxy) phenyl group, 2-fluoro-4- (3-methoxypropoxy) phenyl group, 2-fluoro-4- (4-methoxybutoxy) phenyl group, 2-fluoro-4- (5- Methoxypentyloxy) phenyl group, 2-fluoro-4- (6-methoxyhexyloxy) phenyl group, 2-fluoro-4- (7-methoxyheptyloxy) phenyl group, 2-fluoro-4- (2-ethoxyethoxy) ) Phenyl group, 2-fluoro-4- (3-ethoxypropoxy) phenyl group, 2-fluoro-4- (4-ethoxybutoxy) phenyl group, 2-fluoro-4- (5-ethoxypentyloxy) phenyl group, 2-fluoro-4- (6-ethoxyhexyloxy) phenyl group, 2-fluoro-4- (7-ethoxyheptyloxy) phene Group,
2-fluoro-4-cyclopropylmethoxyphenyl group, 2-fluoro-4- (2-cyclopropylethoxy) phenyl group, 2-fluoro-4- (3-cyclopropylpropoxy) phenyl group, 2-fluoro-4- (4-cyclopropylbutoxy) phenyl group, 2-fluoro-4- (5-cyclopropylpentyloxy) phenyl group, 2-fluoro-4- (6-cyclopropylhexyloxy) phenyl group, 2-fluoro-4- (7-cyclopropylheptyloxy) phenyl group, 2-fluoro-4-phenoxymethylphenyl group, 2-fluoro-4- (2-phenylethyl) phenyl group, 2-fluoro-4- (3-phenylpropyl) phenyl Group, 2-fluoro-4- (4-phenylbutyl) phenyl group, 2-fluoro-4- (5-phenyl) Pentyl) phenyl group, 2-fluoro-4- (2-phenylethoxy) phenyl group, 2-fluoro-4- (3-phenylpropoxy) phenyl group, 2-fluoro-4- (4-phenylbutoxy) phenyl group, 2-fluoro-4- (5-phenylpentyloxy) phenyl group, (Z) -2-fluoro-4-styrylphenyl group,
1-benzylpyrrol-3-yl group, 1- (2-fluorophenylmethyl) pyrrol-3-yl group, 1- (3-fluorophenylmethyl) pyrrol-3-yl group, 1- (4-fluorophenyl) Methyl) pyrrol-3-yl group, 1- (2-phenylethyl) pyrrol-3-yl group, 1-benzylpyrazol-4-yl group, 1-phenylpyrazol-4-yl group, 2-methoxythiazol-5 -Yl group, 2-ethoxythiazol-5-yl group, 2-propoxythiazol-5-yl group, 2-butoxythiazol-5-yl group, 2-pentyloxythiazol-5-yl group, 2-benzyloxythiazole -5-yl group, 2-phenoxythiazol-5-yl group, 2-methylthiazol-5-yl group, 2-butylthiazol-5-yl group, Ruchiazoru 5-yl group, and 2-benzyl-5-yl group.

As an aspect of this compound, the following are mentioned, for example.
An ether compound in which the group represented by E in formula (1) may be substituted with at least one group selected from the following substituent group m-1;
[Substituent Group m-1]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl C1-6 alkyl group, phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, Benzofuryl C1-6 alkyl group, benzothienyl C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, phenoxy group, C3-8 cycloalkyl C1-6 alkoxy group, phenyl C1-6 alkoxy group, furyl C1-6 alkoxy group, thienyl C1-6 alkoxy group, pyridyl C1-6 alkoxy group, phenoxy C1-6 alkyl group, pyridyloxy C1-6 alkyl group, C1-8 haloalkyl group, C1- 6 alkoxy C1-8 alkyl group, C1-6 alkylthio C1-8 al Group, C2-8 haloalkenyl group, C1-6 alkoxy C2-8 alkenyl group, C1-6 alkylthio C2-8 alkenyl group, C2-8 haloalkynyl group, C1-6 alkoxy C2-8 alkynyl group, C1-6 Alkylthio C2-8 alkynyl group, C1-8 haloalkoxy group, C1-6 alkoxy C1-8 alkoxy group, C1-6 alkylthio C1-8 alkoxy group, C2-8 haloalkenyloxy group, C1-6 alkoxy C2-8 alkenyl An oxy group, a C1-6 alkylthio C2-8 alkenyloxy group, a C2-8 haloalkynyloxy group, a C1-6 alkoxy C2-8 alkynyloxy group, and
A C1-6 alkylthio C2-8 alkynyloxy group;
And;
A C3-8 cycloalkyl C1-6 alkyl group substituted with a group selected from the group consisting of a halogen atom, a C1-6 alkoxy group and a C1-6 alkylthio group;
A phenyl C1-6 alkyl group substituted with a group selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A furyl C1-6 alkyl group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A thienyl C1-6 alkyl group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A benzofuryl C1-6 alkyl group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A benzothienyl C1-6 alkyl group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A phenoxy group substituted with a group selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A C3-8 cycloalkyl C1-6 alkoxy group substituted with a group selected from the group consisting of a halogen atom, a C1-6 alkoxy group and a C1-6 alkylthio group;
A phenyl C1-6 alkoxy group substituted with a group selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A furyl C1-6 alkoxy group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A thienyl C1-6 alkoxy group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A pyridyl C1-6 alkoxy group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
A phenoxy C1-6 alkyl group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;
and;
A pyridyloxy C1-6 alkyl group substituted with a group selected from the group consisting of a halogen atom, a cyano group, a trifluoromethyl group, a C1-6 alkyl group, a C1-6 alkoxy group and a C1-6 alkylthio group;

An ether compound in which the group represented by E in formula (1) may be substituted with at least one group selected from the following substituent group i-1;
[Substituent group i-1]
Halogen atoms, C1-8 alkyl groups, C1-8 alkoxy groups, C3-8 alkenyloxy groups, C3-8 alkynyloxy groups, C6-10 aryloxy groups, C6-10 aryl C1-6 alkoxy groups and (C1-C2 Alkoxy) a C2-C5 alkoxy group;
An ether compound in which the group represented by E in formula (1) may be substituted with at least one group selected from the following substituent group j-1;
[Substituent group j-1]
A halogen atom, a C1-8 alkoxy group, a C3-8 alkenyloxy group, a C3-8 alkynyloxy group and a (C1-C2 alkoxy) C2-C5 alkoxy group;

An ether compound in which A is A ¹ in formula (1);
An ether compound in which A is A ² in formula (1);
An ether compound in which A is A ³ in formula (1);
An ether compound in which A is A ¹ , A ² or A ³ and p, q or r is 0 in formula (1);
An ether compound in which A is A ¹ and p is 0 in formula (1);
An ether compound in which A is A ² and q is 0 in formula (1);
An ether compound in which A is A ³ and r is 0 in formula (1);
An ether compound in which n is 1 in formula (1);
An ether compound in which n is 1 or 2 in formula (1);

An ether compound in which n is 2 in formula (1);
An ether compound in which n is 3 in formula (1);
An ether compound in which A is A ¹ and n is 1 in formula (1);
An ether compound in which A is A ² and n is 1 in formula (1);
An ether compound in which A is A ³ and n is 1 in formula (1);
An ether compound in which A is A ¹ and n is 2 in formula (1);
An ether compound in which A is A ² and n is 2 in formula (1);
An ether compound in which A is A ³ and n is 2 in formula (1);

An ether compound in which A is A ¹ , p is 1 or 2, and R ¹ is a halogen atom in formula (1);
An ether compound in which A is A ² , q is 1 or 2, and R ² is a halogen atom in formula (1);
An ether compound in which A is A ³ , r is 1 or 2, and R ³ is a halogen atom in formula (1);
An ether compound in which A is A ¹ , p is 1 or 2, and R ¹ is a fluorine atom in formula (1);
An ether compound in which A is A ² , q is 1 or 2, and R ² is a fluorine atom in formula (1);
An ether compound in which A is A ³ , r is 1 or 2, and R ³ is a fluorine atom in formula (1);

An ether compound in which in formula (1), E is a phenyl group optionally having 1 or 2 substituents selected from the substituent group m-1;
An ether compound in which E is a thienyl group optionally having one or two substituents selected from the substituent group m-1 in the formula (1);

An ether compound in which, in the formula (1), E is a phenyl group substituted with at least one group selected from the substituent group i-1;
An ether compound in which E is a thienyl group substituted with at least one group selected from the substituent group i-1 in formula (1);

An ether compound in which, in formula (1), E is a phenyl group substituted with at least one group selected from the substituent group j-1;
An ether compound in which E is a thienyl group substituted with at least one group selected from the substituent group j-1 in formula (1);

〔式中、Ｅは前記と同じ意味を表す。〕で示されるエーテル化合物；
式（２）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（２）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（２）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（２）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（２）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されたフェニル基であるエーテル化合物；
式（２）において、Ｅが前記の置換基群ａ−３および前記の置換基群ａ−４から選ばれる少なくとも１種の基で置換されたフェニル基であるエーテル化合物；
式（２）において、Ｅが前記の置換基群ｅ−１および前記の置換基群ｅ−２から選ばれる置換基を１または２個有してもよいフェニル基であるエーテル化合物；
式（２）において、Ｅが、前記の置換基群ｇ−１および前記の置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフェニル基であるエーテル化合物；
式（２）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（２）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（２）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されたエーテル化合物；
式（２）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されたフェニル基であるエーテル化合物；
式（２）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されたエーテル化合物；
式（２）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されたフェニル基であるエーテル化合物；
式（２）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（２）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（２）において、Ｅが（Ｃ１−２アルコキシ）Ｃ２−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（２）において、ＥがＣ３−Ｃ８アルケニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（２）において、ＥがＣ３−Ｃ８アルキニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（２）において、ＥがＣ１−Ｃ６アルキル基で置換されたフェニル基であるエーテル化合物；
式（２）において、ＥがＣ６−１０アリールオキシ基で置換されたフェニル基であるエーテル化合物；
式（２）において、Ｅがハロゲン原子で置換されたフェニル基であるエーテル化合物； An ether compound in which A is A ¹ , p is 0 and n is 1 in formula (1), that is, formula (2)

[Wherein E represents the same meaning as described above. An ether compound represented by the formula:
In the formula (2), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group m-1. An ether compound which may be used;
In the formula (2), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group i-1. An ether compound which may be used;
In the formula (2), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group j-1. An ether compound which may be used;
An ether compound in which in formula (2), E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2;
An ether compound in which in formula (2), E is a phenyl group substituted with at least one group selected from the substituent group a-1 and the substituent group a-2;
An ether compound in which in formula (2), E is a phenyl group substituted with at least one group selected from the substituent group a-3 and the substituent group a-4;
An ether compound in which E is a phenyl group which may have one or two substituents selected from the substituent group e-1 and the substituent group e-2 in the formula (2);
An ether compound in which in formula (2), E is a phenyl group which may have one or two substituents selected from the substituent group g-1 and the substituent group g-2;
An ether compound in which E in formula (2) may be substituted with at least one group selected from the substituent group m-1;
An ether compound in which in formula (2), E is a phenyl group optionally substituted with at least one group selected from the substituent group m-1;
An ether compound in which E is substituted with at least one group selected from the substituent group i-1 in the formula (2);
An ether compound in which E is a phenyl group substituted with at least one group selected from the substituent group i-1 in formula (2);
An ether compound in which E is substituted with at least one group selected from the substituent group j-1 in the formula (2);
An ether compound in which E is a phenyl group substituted with at least one group selected from the above-mentioned substituent group j-1 in formula (2);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (2);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (2);
An ether compound in which E is a phenyl group substituted with a (C1-2 alkoxy) C2-C6 alkoxy group in formula (2);
An ether compound in which E is a phenyl group substituted by a C3-C8 alkenyloxy group in formula (2);
An ether compound in which E is a phenyl group substituted by a C3-C8 alkynyloxy group in formula (2);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkyl group in formula (2);
An ether compound in which E is a phenyl group substituted with a C6-10 aryloxy group in formula (2);
An ether compound in which E is a phenyl group substituted with a halogen atom in formula (2);

〔式中、Ｅは前記と同じ意味を表す。〕で示されるエーテル化合物；
式（３）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（３）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（３）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（３）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（３）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（３）において、Ｅが前記の置換基群ａ−３および前記の置換基群ａ−４から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（３）において、Ｅが前記の置換基群ｅ−１および前記の置換基群ｅ−２から選ばれる置換基を１または２個有してもよいフェニル基であるエーテル化合物；
式（３）において、Ｅが、前記の置換基群ｇ−１および前記の置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフェニル基であるエーテル化合物；
式（３）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（３）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（３）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（３）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（３）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（３）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；式（３）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（３）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（３）において、Ｅが（Ｃ１−２アルコキシ）Ｃ２−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（３）において、ＥがＣ３−Ｃ８アルケニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（３）において、ＥがＣ３−Ｃ８アルキニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（３）において、ＥがＣ１−Ｃ６アルキル基で置換されたフェニル基であるエーテル化合物；
式（３）において、ＥがＣ６−１０アリールオキシ基で置換されたフェニル基であるエーテル化合物；
式（３）において、Ｅがハロゲン原子で置換されたフェニル基であるエーテル化合物；
式（３）において、ＥがＣ６−１０アリールＣ１−６アルコキシ基で置換されたフェニル基であるエーテル化合物； An ether compound in which A is A ¹ , p is 0, and n is 2 in formula (1), that is, formula (3)

[Wherein E represents the same meaning as described above. An ether compound represented by the formula:
In Formula (3), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and each group represented by E is substituted with at least one group selected from the substituent group m-1. An ether compound which may be used;
In the formula (3), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group i-1. An ether compound which may be used;
In the formula (3), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group j-1. An ether compound which may be used;
An ether compound in which in formula (3), E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2;
An ether compound in which in formula (3), E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2;
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from the substituent group a-3 and the substituent group a-4 in formula (3);
An ether compound in which in formula (3), E is a phenyl group which may have one or two substituents selected from the substituent group e-1 and the substituent group e-2;
An ether compound in which in formula (3), E is a phenyl group optionally having one or two substituents selected from the substituent group g-1 and the substituent group g-2;
In formula (3), E may be an ether compound which may be substituted with at least one group selected from the substituent group m-1.
In formula (3), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the aforementioned substituent group m-1;
In formula (3), E may be an ether compound which may be substituted with at least one group selected from the substituent group i-1;
In formula (3), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the substituent group i-1;
In formula (3), E may be an ether compound optionally substituted with at least one group selected from the above substituent group j-1;
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from the above-mentioned substituent group j-1 in formula (3); in formula (3), E is a C1-C6 alkoxy An ether compound which is a phenyl group substituted by a group;
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (3);
An ether compound in which E is a phenyl group substituted by a (C1-2 alkoxy) C2-C6 alkoxy group in formula (3);
An ether compound in which E is a phenyl group substituted by a C3-C8 alkenyloxy group in formula (3);
An ether compound in which E is a phenyl group substituted with a C3-C8 alkynyloxy group in formula (3);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkyl group in formula (3);
An ether compound in which E is a phenyl group substituted with a C6-10 aryloxy group in formula (3);
An ether compound in which E is a phenyl group substituted by a halogen atom in formula (3);
An ether compound in which E is a phenyl group substituted with a C6-10 aryl C1-6 alkoxy group in formula (3);

〔式中、Ｅは前記と同じ意味を表す。〕で示されるエーテル化合物；
式（４）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（４）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（４）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（４）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（４）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（４）において、Ｅが前記の置換基群ａ−３および前記の置換基群ａ−４から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（４）において、Ｅが前記の置換基群ｅ−１および前記の置換基群ｅ−２から選ばれる置換基を１または２個有してもよいフェニル基であるエーテル化合物；
式（４）において、Ｅが前記の置換基群ｇ−１および前記の置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフェニル基であるエーテル化合物；
式（４）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（４）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（４）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（４）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（４）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（４）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；

式（４）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（４）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（４）において、Ｅが（Ｃ１−２アルコキシ）Ｃ２−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（４）において、ＥがＣ３−Ｃ８アルケニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（４）において、ＥがＣ３−Ｃ８アルキニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（４）において、ＥがＣ１−Ｃ６アルキル基で置換されたフェニル基であるエーテル化合物；
式（４）において、ＥがＣ６−１０アリールオキシ基で置換されたフェニル基であるエーテル化合物；
式（４）において、Ｅがハロゲン原子で置換されたフェニル基であるエーテル化合物；
式（４）において、ＥがＣ６−１０アリールＣ１−６アルコキシ基で置換されたフェニル基であるエーテル化合物； In the formula (1), an ether compound in which A is A ³ , r is 0, and n is 1, that is, the formula (4)

[Wherein E represents the same meaning as described above. An ether compound represented by the formula:
In the formula (4), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and each group represented by E is substituted with at least one group selected from the substituent group m-1. Ether compounds which may have been prepared;
In the formula (4), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and all the groups represented by E are substituted with at least one group selected from the substituent group i-1. Ether compounds which may have been prepared;
In the formula (4), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group j-1. Ether compounds which may have been prepared;
An ether compound in which in formula (4), E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2;
An ether compound in which in formula (4), E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2;
In formula (4), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from substituent group a-3 and substituent group a-4;
An ether compound in which in formula (4), E is a phenyl group which may have one or two substituents selected from the substituent group e-1 and the substituent group e-2;
An ether compound in which in formula (4), E is a phenyl group optionally having one or two substituents selected from the substituent group g-1 and the substituent group g-2;
In formula (4), E may be an ether compound optionally substituted with at least one group selected from the substituent group m-1;
In formula (4), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the above substituent group m-1;
In formula (4), E is an ether compound optionally substituted with at least one group selected from the substituent group i-1.
An ether compound in which in formula (4), E is a phenyl group optionally substituted with at least one group selected from the substituent group i-1;
In formula (4), E is an ether compound optionally substituted with at least one group selected from the substituent group j-1;
In formula (4), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the above substituent group j-1;

An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (4);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (4);
An ether compound in which E is a phenyl group substituted with a (C1-2 alkoxy) C2-C6 alkoxy group in formula (4);
An ether compound in which E is a phenyl group substituted with a C3-C8 alkenyloxy group in formula (4);
An ether compound in which E is a phenyl group substituted with a C3-C8 alkynyloxy group in formula (4);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkyl group in formula (4);
An ether compound in which E is a phenyl group substituted with a C6-10 aryloxy group in formula (4);
An ether compound in which E is a phenyl group substituted with a halogen atom in formula (4);
An ether compound in which E is a phenyl group substituted with a C6-10 aryl C1-6 alkoxy group in formula (4);

〔式中、Ｅは前記と同じ意味を表す。〕で示されるエーテル化合物；
式（５）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（５）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（５）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（５）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（５）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（５）において、Ｅが前記の置換基群ａ−３および前記の置換基群ａ−４から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（５）において、Ｅが前記の置換基群ｅ−１および前記の置換基群ｅ−２から選ばれる置換基を１または２個有してもよいフェニル基であるエーテル化合物；
式（５）において、Ｅが、前記の置換基群ｇ−１および前記の置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフェニル基であるエーテル化合物；
式（５）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（５）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（５）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（５）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（５）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（５）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（５）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（５）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（５）において、Ｅが（Ｃ１−２アルコキシ）Ｃ２−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（５）において、ＥがＣ３−Ｃ８アルケニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（５）において、ＥがＣ３−Ｃ８アルキニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（５）において、ＥがＣ１−Ｃ６アルキル基で置換されたフェニル基であるエーテル化合物；
式（５）において、ＥがＣ６−１０アリールオキシ基で置換されたフェニル基であるエーテル化合物；
式（５）において、Ｅがハロゲン原子で置換されたフェニル基であるエーテル化合物；
式（５）において、ＥがＣ６−１０アリールＣ１−６アルコキシ基で置換されたフェニル基であるエーテル化合物；
In the formula (1), an ether compound in which A is A ³ , r is 0, and n is 2, that is, the formula (5)

[Wherein E represents the same meaning as described above. An ether compound represented by the formula:
In Formula (5), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group m-1. An ether compound which may be used;
In the formula (5), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group i-1. An ether compound which may be used;
In the formula (5), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group j-1. An ether compound which may be used;
An ether compound in which in formula (5), E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2;
An ether compound in which in formula (5), E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2;
In formula (5), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the above substituent group a-3 and the above substituent group a-4;
An ether compound in which in formula (5), E is a phenyl group which may have one or two substituents selected from the substituent group e-1 and the substituent group e-2;
An ether compound in which in formula (5), E is a phenyl group optionally having one or two substituents selected from the substituent group g-1 and the substituent group g-2;
An ether compound in which E is optionally substituted with at least one group selected from the substituent group m-1 in formula (5);
In formula (5), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the aforementioned substituent group m-1;
In formula (5), E may be an ether compound optionally substituted with at least one group selected from the substituent group i-1;
In formula (5), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the above substituent group i-1;
In formula (5), E may be an ether compound which may be substituted with at least one group selected from the above substituent group j-1;
In formula (5), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the above substituent group j-1;
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (5);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (5);
An ether compound in which E is a phenyl group substituted by a (C1-2 alkoxy) C2-C6 alkoxy group in formula (5);
An ether compound in which E is a phenyl group substituted with a C3-C8 alkenyloxy group in formula (5);
An ether compound in which E is a phenyl group substituted by a C3-C8 alkynyloxy group in formula (5);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkyl group in formula (5);
An ether compound in which E is a phenyl group substituted with a C6-10 aryloxy group in formula (5);
An ether compound in which E is a phenyl group substituted with a halogen atom in formula (5);
An ether compound in which E is a phenyl group substituted with a C6-10 aryl C1-6 alkoxy group in formula (5);

〔式中、Ｅは前記と同じ意味を表す。〕で示されるエーテル化合物；
式（６）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（６）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（６）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（６）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（６）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（６）において、Ｅが前記の置換基群ａ−３および前記の置換基群ａ−４から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（６）において、Ｅが前記の置換基群ｅ−１および前記の置換基群ｅ−２から選ばれる置換基を１または２個有してもよいフェニル基であるエーテル化合物；
式（６）において、Ｅが、前記の置換基群ｇ−１および前記の置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフェニル基であるエーテル化合物；
式（６）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（６）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（６）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（６）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（６）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（６）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；式（６）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（６）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（６）において、Ｅが（Ｃ１−２アルコキシ）Ｃ２−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（６）において、ＥがＣ３−Ｃ８アルケニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（６）において、ＥがＣ３−Ｃ８アルキニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（６）において、ＥがＣ１−Ｃ６アルキル基で置換されたフェニル基であるエーテル化合物；
式（６）において、ＥがＣ６−１０アリールオキシ基で置換されたフェニル基であるエーテル化合物；
式（６）において、Ｅがハロゲン原子で置換されたフェニル基であるエーテル化合物；
式（６）において、ＥがＣ６−１０アリールＣ１−６アルコキシ基で置換されたフェニル基であるエーテル化合物； An ether compound in which A is A ² , q is 0 and n is 1 in formula (1), that is, formula (6)

[Wherein E represents the same meaning as described above. An ether compound represented by the formula:
In Formula (6), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group m-1. An ether compound which may be used;
In the formula (6), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group i-1. An ether compound which may be used;
In Formula (6), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group j-1 described above. An ether compound which may be used;
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from substituent group a-1 and substituent group a-2 in formula (6);
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from substituent group a-1 and substituent group a-2 in formula (6);
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from the substituent group a-3 and the substituent group a-4 in formula (6);
An ether compound in which in formula (6), E is a phenyl group which may have one or two substituents selected from the substituent group e-1 and the substituent group e-2;
An ether compound in which, in formula (6), E is a phenyl group optionally having one or two substituents selected from the substituent group g-1 and the substituent group g-2;
In formula (6), E may be an ether compound optionally substituted with at least one group selected from the substituent group m-1.
In formula (6), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the aforementioned substituent group m-1;
In formula (6), an ether compound in which E is optionally substituted with at least one group selected from the aforementioned substituent group i-1;
In formula (6), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the above substituent group i-1;
An ether compound in which E in formula (6) may be substituted with at least one group selected from the substituent group j-1;
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from the substituent group j-1 in formula (6); in formula (6), E is a C1-C6 alkoxy; An ether compound which is a phenyl group substituted by a group;
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (6);
An ether compound in which E is a phenyl group substituted by a (C1-2 alkoxy) C2-C6 alkoxy group in formula (6);
An ether compound in which E is a phenyl group substituted with a C3-C8 alkenyloxy group in formula (6);
An ether compound in which E is a phenyl group substituted with a C3-C8 alkynyloxy group in formula (6);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkyl group in formula (6);
An ether compound in which E is a phenyl group substituted with a C6-10 aryloxy group in formula (6);
An ether compound in which E is a phenyl group substituted with a halogen atom in formula (6);
An ether compound in which E is a phenyl group substituted with a C6-10 aryl C1-6 alkoxy group in formula (6);

〔式中、Ｅは前記と同じ意味を表す。〕で示されるエーテル化合物；
式（７）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（７）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（７）において、Ｅが、フリル基、チエニル基、ピロリル基、フェニル基であり、Ｅで示される基はいずれも、前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（７）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（７）において、Ｅが前記の置換基群ａ−１および前記の置換基群ａ−２から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（７）において、Ｅが前記の置換基群ａ−３および前記の置換基群ａ−４から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（７）において、Ｅが前記の置換基群ｅ−１および前記の置換基群ｅ−２から選ばれる置換基を１または２個有してもよいフェニル基であるエーテル化合物；
式（７）において、Ｅが、前記の置換基群ｇ−１および前記の置換基群ｇ−２から選ばれる置換基を１または２個有していてもよいフェニル基であるエーテル化合物；
式（７）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（７）において、Ｅが前記の置換基群ｍ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（７）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（７）において、Ｅが前記の置換基群ｉ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（７）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいエーテル化合物；
式（７）において、Ｅが前記の置換基群ｊ−１から選ばれる少なくとも１種の基で置換されていてもよいフェニル基であるエーテル化合物；
式（７）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（７）において、ＥがＣ１−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（７）において、Ｅが（Ｃ１−２アルコキシ）Ｃ２−Ｃ６アルコキシ基で置換されたフェニル基であるエーテル化合物；
式（７）において、ＥがＣ３−Ｃ８アルケニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（７）において、ＥがＣ３−Ｃ８アルキニルオキシ基で置換されたフェニル基であるエーテル化合物；
式（５）において、ＥがＣ１−Ｃ６アルキル基で置換されたフェニル基であるエーテル化合物；
式（７）において、ＥがＣ６−１０アリールオキシ基で置換されたフェニル基であるエーテル化合物；
式（７）において、Ｅがハロゲン原子で置換されたフェニル基であるエーテル化合物；
式（７）において、ＥがＣ６−１０アリールＣ１−６アルコキシ基で置換されたフェニル基であるエーテル化合物。 An ether compound in which A is A ² , q is 0 and n is 2 in formula (1), that is, formula (7)

[Wherein E represents the same meaning as described above. An ether compound represented by the formula:
In Formula (7), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group m-1. An ether compound which may be used;
In the formula (7), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group i-1. An ether compound which may be used;
In Formula (7), E is a furyl group, a thienyl group, a pyrrolyl group, or a phenyl group, and any group represented by E is substituted with at least one group selected from the substituent group j-1. An ether compound which may be used;
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2 in formula (7);
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from the substituent group a-1 and the substituent group a-2 in formula (7);
An ether compound in which E is a phenyl group optionally substituted with at least one group selected from substituent group a-3 and substituent group a-4 in formula (7);
An ether compound in which E is a phenyl group optionally having one or two substituents selected from substituent group e-1 and substituent group e-2 in formula (7);
An ether compound in which E is a phenyl group optionally having one or two substituents selected from the substituent group g-1 and the substituent group g-2 in the formula (7);
In formula (7), an ether compound in which E may be substituted with at least one group selected from the substituent group m-1;
In formula (7), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the aforementioned substituent group m-1;
An ether compound in which E in formula (7) may be substituted with at least one group selected from the substituent group i-1;
In formula (7), an ether compound in which E is a phenyl group optionally substituted with at least one group selected from the aforementioned substituent group i-1;
An ether compound in which E in formula (7) may be substituted with at least one group selected from the substituent group j-1;
An ether compound in which in formula (7), E is a phenyl group optionally substituted with at least one group selected from the substituent group j-1;
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (7);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkoxy group in formula (7);
An ether compound in which E is a phenyl group substituted by a (C1-2 alkoxy) C2-C6 alkoxy group in formula (7);
An ether compound in which E is a phenyl group substituted by a C3-C8 alkenyloxy group in formula (7);
An ether compound in which E is a phenyl group substituted with a C3-C8 alkynyloxy group in formula (7);
An ether compound in which E is a phenyl group substituted with a C1-C6 alkyl group in formula (5);
An ether compound in which E is a phenyl group substituted with a C6-10 aryloxy group in formula (7);
An ether compound in which E is a phenyl group substituted with a halogen atom in formula (7);
An ether compound in which E is a phenyl group substituted with a C 6-10 aryl C 1-6 alkoxy group in formula (7).

The present compound can be produced by the production method described in the international patent application WO2005 / 033079 pamphlet (Patent Document 1) or the production examples described later.
Moreover, this compound can also be manufactured by the following (manufacturing method 1)-(manufacturing method 3), for example.

〔式中、Ａ、Ｅ及びｎは前記と同じ意味を表し、Ｌは塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基又はｐ−トルエンスルホニルオキシ基を表す。〕
該反応は、通常溶媒の存在下で行われる。
該反応に用いられる溶媒としては、例えばテトラヒドロフラン（以下、ＴＨＦと記す場合がある。）、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル（以下、ＭＴＢＥと記す場合がある。）等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド（以下、ＤＭＦと記す場合がある。）等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、水及びこれらの混合物が挙げられる。
該反応に用いられる塩基としては、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩類、水酸化ナトリウム等のアルカリ金属水酸化物類、水素化ナトリウム等のアルカリ金属水素化物類等が挙げられる。
化合物（８）１モルに対して、化合物（９）が通常１〜１０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０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加えた後、固体が析出した場合は、濾過することにより本化合物を単離することができ、また、固体が析出しない場合は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本化合物を単離することができる。単離された本化合物は、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)
This compound can be produced by reacting compound (8) with compound (9) in the presence of a base.

[Wherein, A, E and n represent the same meaning as described above, and L represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group or a p-toluenesulfonyloxy group. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter sometimes referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether (hereinafter sometimes referred to as MTBE), toluene, Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide (hereinafter sometimes referred to as DMF), dimethyl sulfoxide, etc. Sulfoxides, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydroxides such as sodium hydroxide, alkali metal hydrides such as sodium hydride, and the like. .
The compound (9) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (8).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, after adding water to the reaction mixture, if a solid precipitates, the compound can be isolated by filtration. If the solid does not precipitate, the reaction mixture is washed with an organic solvent. The compound can be isolated by performing post-treatment operations such as extraction, drying and concentration of the organic layer. The isolated present compound can be further purified by chromatography, recrystallization and the like.

〔式中、Ａ、Ｅ及びｎ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、トルエン、ヘキサン等の炭化水素類、ＴＨＦ、ＭＴＢＥ等のエーテル類、クロロベンゼン等のハロゲン化炭化水素類、ＤＭＦ等の酸アミド類等及びこれらの混合物が挙げられる。
縮合剤としては、アゾジカルボン酸ジエチル（以下、ＤＥＡＤと記す場合がある。）及びトリフェニルホスフィンからなる試剤が挙げられる。
化合物（１０）1モルに対して、化合物（８）は、通常0.5モル〜過剰量の割合、好ましくは1モル〜1.5モルの割合であり、縮合剤がＤＥＡＤ及びトリフェニルホスフィンからなる試剤の場合、化合物（１０）1モルに対して、ＤＥＡＤは通常0.8〜2モルの割合、好ましくは1モル〜2モルの割合、トリフェニルホスフィンは通常0.8〜2モルの割合、好ましくは1モル〜2モルの割合で用いられる。
該反応の反応温度は通常−２０℃から反応に使用する溶媒の沸点または１００℃までの範囲であり、反応時間は通常５分間〜２４時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本化合物を単離することができる。単離された本化合物は、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)
This compound can be produced by reacting the compound (8) and the alcohol compound represented by the compound (10) in the presence of a condensing agent.

[Wherein, A, E and n 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 hydrocarbons such as toluene and hexane, ethers such as THF and MTBE, halogenated hydrocarbons such as chlorobenzene, acid amides such as DMF, and the like, and mixtures thereof.
Examples of the condensing agent include a reagent comprising diethyl azodicarboxylate (hereinafter sometimes referred to as DEAD) and triphenylphosphine.
Compound (8) is usually in a proportion of 0.5 mol to excess, preferably 1 mol to 1.5 mol, and the condensing agent is a reagent consisting of DEAD and triphenylphosphine with respect to 1 mol of compound (10). , DEAD is usually 0.8 to 2 mol, preferably 1 to 2 mol, and triphenylphosphine is usually 0.8 to 2 mol, preferably 1 to 2 mol, per 1 mol of compound (10). It is used in the ratio.
The reaction temperature of the reaction is usually in the range from −20 ° C. to the boiling point of the solvent used in the reaction or 100 ° C., and the reaction time is usually in the range of 5 minutes to 24 hours.
After completion of the reaction, this compound can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated present compound can be further purified by chromatography, recrystallization and the like.

〔式中、Ａ、Ｌ及びｎは前記と同じ意味を表し、Ｒ⁴はＣ１−８アルキル基、Ｃ３−８アルケニル基、Ｃ３−８アルキニル基、Ｃ６−１０アリールＣ１−６アルキル基、Ｃ１−６アルコキシＣ１−８アルキル基、Ｃ３−８シクロアルキルＣ１−６アルキル基、フェニルＣ１−６アルキル基、フリルＣ１−６アルキル基、チエニルＣ１−６アルキル基、ピリジルＣ１−６アルキル基、フェノキシＣ１−６アルキル基、ピリジルオキシＣ１−６アルキル基、Ｃ１−８ハロアルコキシ基、Ｃ１−６アルキルチオＣ１−８アルキル基、Ｃ２−８ハロアルケニル基、Ｃ１−６アルコキシＣ２−８アルケニル基、Ｃ１−６アルキルチオＣ２−８アルケニル基、Ｃ２−８ハロアルキニル基、Ｃ１−６アルコキシＣ２−８アルキニル基またはＣ１−６アルキルチオＣ２−８アルキニル基を表す。〕
該反応は、通常溶媒の存在下で行われる。
該反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ＭＴＢＥ等のエーテル類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、アセトニトリル等のニトリル類、ＤＭＦ等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、水及びこれらの混合物が挙げられる。
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、炭酸セシウム等のアルカリ金属炭酸塩類、水酸化ナトリウム等のアルカリ金属水酸化物類、水素化ナトリウム等のアルカリ金属水素化物類等が挙げられる。
化合物（１１）１モルに対して、化合物（１２）が通常１〜１０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０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加えた後、固体が析出した場合は、濾過することにより化合物（ＩＩ）を単離することができ、また、固体が析出しない場合は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物（ＩＩ）を単離することができる。単離された化合物（ＩＩ）は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 3)
Among these compounds, compound (II) can be produced by reacting compound (11) in which E is a phenyl group substituted with a hydroxyl group with compound (12) in the presence of a base.

[Wherein, A, L and n represent the same meaning as described above, and R ⁴ represents a C 1-8 alkyl group, a C 3-8 alkenyl group, a C 3-8 alkynyl group, a C 6-10 aryl C 1-6 alkyl group, a C 1- 6 alkoxy C1-8 alkyl group, C3-8 cycloalkyl C1-6 alkyl group, phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, pyridyl C1-6 alkyl group, phenoxy C1- 6 alkyl group, pyridyloxy C1-6 alkyl group, C1-8 haloalkoxy group, C1-6 alkylthio C1-8 alkyl group, C2-8 haloalkenyl group, C1-6 alkoxy C2-8 alkenyl group, C1-6 alkylthio C2-8 alkenyl group, C2-8 haloalkynyl group, C1-6 alkoxy C2-8 alkynyl group or C1-6 alkyl Representing your C2-8 alkynyl group. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, nitriles such as acetonitrile, DMF, and the like. Acid amides, sulfoxides such as dimethyl sulfoxide, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, water, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydroxides such as sodium hydroxide, alkali metal hydrides such as sodium hydride, and the like. .
The compound (12) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (11).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, after adding water to the reaction mixture, if a solid is precipitated, the compound (II) can be isolated by filtration. If no solid is precipitated, the reaction mixture is organically mixed. Compound (II) can be isolated by performing post-treatment operations such as extraction with a solvent and drying and concentration of an organic layer. The isolated compound (II) can be further purified by chromatography, recrystallization and the like.

  In the agricultural composition of the present invention, this compound is usually mixed with a liquid carrier, solid carrier, gas carrier, surfactant and the like, and if necessary, an auxiliary for formulation such as a binder and a thickener is added, It is formulated into wettable powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule and the like. These preparations usually contain the present compound in a weight ratio of 0.1 to 99%, preferably 0.2 to 90%.

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

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

  Surfactants are usually used as emulsifiers, dispersants, spreaders, penetrants, wetting agents and the like used in the formulation. Examples of surfactants include anions such as alkyl sulfate ester salts, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate esters, lignin sulfonates, and naphthalene sulfonate formaldehyde polycondensates. Nonionic surfactants such as surfactants and polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters and the like can be mentioned. Two or more kinds of these surfactants can be used. The surfactant is usually used in a proportion of 0.1 to 50% by weight, preferably about 0.1 to 25% by weight, based on the whole preparation.

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

  In addition, the agricultural composition of the present invention may be mixed with or without mixing with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers or soil conditioners. It can also be used.

  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; pyramethostrobin; pyroxystrobin; spiroxamine; quinoxifene; fenhexamide; famoxadone; fenamidone: zoxamide; Amisulbrom; iprovaricarb; bench avaricarb; cyazofamide; Dipropamide; Boscalid; Penthiopyrad; Metrafenone; Fluopyran; Bixafen; Ciflufenamide; Proquinazide; Orizastrobin; Framethopil; Tifluzamide; Mepronil; Phenoxanyl; tricyclazole; pyroxilone; probenazole; isothianyl; thiazinyl; tebufloquine; diclomedin; kasugamycin; ferrimzone; Cupric chloride; basic copper sulfate; organic copper; sulfur; amethoctrazine; penflufen, sedaxane, isopyrazam; varifenalate and the like.

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

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

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

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

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

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

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

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

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

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

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

  The method of applying the agricultural composition of the present invention is not particularly limited as long as the agricultural composition of the present invention can be applied substantially. For example, to a plant of a useful plant crop such as foliage spraying. , Treatment of cultivated land such as planted or planted soil of useful crop plants, treatment of seeds such as seed disinfection, and the like.

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

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

Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplant, tomato, pepper, pepper, potato Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae (burdock, Shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, red pepper, etc.), red crustacean vegetables (spinach, chard, etc.) (Perilla, mint, basil ), Strawberry, sweet potato, yam, taro, etc.,
Flower buds;
Foliage plant;
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, 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.
Others: Biofuel plants (Jatropha curcas, safflower, Amanas, switchgrass, Miss Kansas, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.)

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

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

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

In addition, as toxins expressed in such genetically modified crops, hybrids of insecticidal proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, and the like, δ-endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A Toxins, partially defective toxins, modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant 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 that expresses Cry1Ab toxin), YieldGuard Rootworm® (a corn variety that expresses Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1) Corn varieties expressing toxin), Herculex I® (corn varieties expressing phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties that express), Bollgard I (registered trademark) (cotton varieties that express Cry1Ac toxin), Bollgard II (registered trademark) (Cry1Ac and cotton varieties expressing ry2Ab toxin), VIPCOT® (cotton varieties expressing VIP toxin), NewLeaf® (potato varieties expressing Cry3A toxin), NatureGard® Agriure® Examples include GT Advantage (GA21 glyphosate resistant trait), Agurisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), Protecta (registered trademark), and the like.

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

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

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

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

¹H-NMR (CDCl₃) δ: 5.26 (2H, s), 7.12-7.19 (3H, m), 7.36 (2H, dd, J = 8.3, 4.4 Hz), 7.45 (1H, dd, J = 9.1, 2.8 Hz), 7.56 (1H, t, J = 7.7 Hz), 8.04 (2H, t, J = 9.9 Hz), 8.78 (1H, dd, J = 4.3, 1.6 Hz). Production Example 1
To a mixed solution of 0.096 g of 55% sodium hydride (oily) and 3 ml of N, N-dimethylformamide (hereinafter sometimes referred to as DMF), 0.29 g of quinolin-6-ol was added under ice cooling, Then, a mixed solution of 0.28 g of 2-fluorobenzyl chloride and 2 ml of DMF was added. Water was added to the reaction mixture stirred overnight at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.40 g of [(2-fluorophenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 1).
Compound 1

¹ H-NMR (CDCl ₃ ) δ: 5.26 (2H, s), 7.12-7.19 (3H, m), 7.36 (2H, dd, J = 8.3, 4.4 Hz), 7.45 (1H, dd, J = 9.1, 2.8 Hz), 7.56 (1H, t, J = 7.7 Hz), 8.04 (2H, t, J = 9.9 Hz), 8.78 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 2.42 (3H, s), 5.16 (2H, s), 7.19 (1H, d, J = 2.7 Hz), 7.22-7.31 (3H, m), 7.36 (1H, dd, J = 8.3, 4.1 Hz), 7.43-7.46 (2H, m), 8.02 (1H, d, J = 9.3 Hz), 8.06 (1H, dd, J = 8.4, 1.6 Hz), 8.78 (1H, dd, J = 4.1, 1.5 Hz). Production Example 2
To a mixed solution of 0.096 g of 55% sodium hydride (oil) and 3 ml of DMF, 0.29 g of quinolin-6-ol was added under ice cooling, and then a mixed solution of 0.37 g of 2-methylbenzyl bromide and 2 ml of DMF was added. . Water was added to the reaction mixture stirred at room temperature for 3 hours, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.33 g of [(2-methylphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 2).
Compound 2

¹ H-NMR (CDCl ₃ ) δ: 2.42 (3H, s), 5.16 (2H, s), 7.19 (1H, d, J = 2.7 Hz), 7.22-7.31 (3H, m), 7.36 (1H, dd , J = 8.3, 4.1 Hz), 7.43-7.46 (2H, m), 8.02 (1H, d, J = 9.3 Hz), 8.06 (1H, dd, J = 8.4, 1.6 Hz), 8.78 (1H, dd, J = 4.1, 1.5 Hz).

¹H-NMR (CDCl₃) δ: 3.89 (3H, s), 5.24 (2H, s), 6.94 (1H, d, J = 8.3 Hz), 7.00 (1H, t, J = 7.4 Hz), 7.19 (1H, d, J = 2.7 Hz), 7.30-7.35 (2H, m), 7.47 (1H, dd, J = 9.3, 2.9 Hz), 7.50 (1H, dt, J = 7.6, 0.9 Hz), 8.00-8.04 (2H, m), 8.76 (1H, dd, J = 4.3, 1.6 Hz). Production Example 3
To a mixed solution of 55% sodium hydride (oil-based) 0.096 g and DMF 3 ml, add 0.29 g of quinolin-6-ol under ice-cooling, and then add a mixed solution of 2-methoxybenzylchlorad 0.31 g and DMF 2 ml. It was. Water was added to the reaction mixture stirred at room temperature for 5 hours, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.44 g of [(2-methoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 3).
Compound 3

¹ H-NMR (CDCl ₃ ) δ: 3.89 (3H, s), 5.24 (2H, s), 6.94 (1H, d, J = 8.3 Hz), 7.00 (1H, t, J = 7.4 Hz), 7.19 ( 1H, d, J = 2.7 Hz), 7.30-7.35 (2H, m), 7.47 (1H, dd, J = 9.3, 2.9 Hz), 7.50 (1H, dt, J = 7.6, 0.9 Hz), 8.00-8.04 (2H, m), 8.76 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 5.19 (2H, s), 7.04 (1H, td, J = 8.4, 2.4 Hz), 7.13 (1H, d, J = 2.7 Hz), 7.21 (1H, dd, J = 9.4, 1.8 Hz), 7.24-7.26 (1H, m), 7.34-7.40 (2H, m), 7.46 (1H, dd, J = 9.0, 2.9 Hz), 8.03 (2H, d, J = 8.5 Hz), 8.79 (1H, dd, J = 4.1, 1.7 Hz). Production Example 4
To a mixed solution of 0.096 g of 55% sodium hydride (oil) and 3 ml of DMF, 0.29 g of quinolin-6-ol was added under ice cooling, and then a mixed solution of 0.37 g of 3-fluorobenzyl bromide and 2 ml of DMF was added. . Water was added to the reaction mixture stirred at room temperature for 5 hours, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.40 g of [(3-fluorophenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 4).
Compound 4

¹ H-NMR (CDCl ₃ ) δ: 5.19 (2H, s), 7.04 (1H, td, J = 8.4, 2.4 Hz), 7.13 (1H, d, J = 2.7 Hz), 7.21 (1H, dd, J = 9.4, 1.8 Hz), 7.24-7.26 (1H, m), 7.34-7.40 (2H, m), 7.46 (1H, dd, J = 9.0, 2.9 Hz), 8.03 (2H, d, J = 8.5 Hz) , 8.79 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 2.39 (3H, s), 5.15 (2H, s), 7.15-7.18 (2H, m), 7.26-7.36 (4H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.4, 1.5 Hz). Production Example 5
To a mixed solution of 0.096 g of 55% sodium hydride (oil) and 3 ml of DMF, 0.29 g of quinolin-6-ol was added under ice cooling, and then a mixed solution of 0.28 g of 3-methylbenzyl chloride and 2 ml of DMF was added. . Water was added to the reaction mixture stirred at room temperature for 5 hours, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.34 g of [(3-methylphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 5).
Compound 5

¹ H-NMR (CDCl ₃ ) δ: 2.39 (3H, s), 5.15 (2H, s), 7.15-7.18 (2H, m), 7.26-7.36 (4H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.4, 1.5 Hz).

¹H-NMR (CDCl₃) δ: 3.83 (3H, s) , 5.17 (2H, s) , 6.88 (1H, dd, J = 8.3, 2.2 Hz), 7.04-7.07 (2H, m), 7.15 (1H, d, J = 2.9 Hz), 7.31-7.36 (2H, m), 7.45-7.48 (1H, m), 8.01-8.05 (2H, m), 8.77-8.78 (1H, m). Production Example 6
To a mixture of 0.29 g of quinolin-6-ol, 0.31 g of 3-methoxybenzyl chloride and 5 ml of DMF was added 0.09 g of 55% sodium hydride (oil) under ice cooling under a nitrogen atmosphere, and the mixture was stirred at room temperature for 4 hours. Stir. Ice and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine (3 times), dried, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.44 g of [(3-methoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 6).
Compound 6

¹ H-NMR (CDCl ₃ ) δ: 3.83 (3H, s), 5.17 (2H, s), 6.88 (1H, dd, J = 8.3, 2.2 Hz), 7.04-7.07 (2H, m), 7.15 (1H , d, J = 2.9 Hz), 7.31-7.36 (2H, m), 7.45-7.48 (1H, m), 8.01-8.05 (2H, m), 8.77-8.78 (1H, m).

¹H-NMR (CDCl₃) δ: 3.92 (3H, s), 5.28 (2H, d, J = 1.2 Hz), 6.95-7.00 (1H, m), 7.09-7.15 (2H, m), 7.19 (1H, d, J = 2.7 Hz), 7.36 (1H, dd, J = 8.3, 4.1 Hz), 7.45 (1H, dd, J = 9.1, 2.8 Hz), 8.02 (1H, d, J = 9.3 Hz), 8.06 (1H, dd, J = 8.4, 1.1 Hz), 8.78 (1H, dd, J = 4.3, 1.6 Hz). Production Example 7
To a mixed solution of 0.14 g of quinolin-6-ol, 0.20 g of (2-fluoro-3-methoxyphenyl) methyl-methanesulfonate and 3 ml of DMF, 0.33 g of cesium carbonate was added. Water was added to the reaction mixture stirred at room temperature for 5 hours, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.40 g of [(2-fluoro-3-methoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 7). .
Compound 7

¹ H-NMR (CDCl ₃ ) δ: 3.92 (3H, s), 5.28 (2H, d, J = 1.2 Hz), 6.95-7.00 (1H, m), 7.09-7.15 (2H, m), 7.19 (1H , d, J = 2.7 Hz), 7.36 (1H, dd, J = 8.3, 4.1 Hz), 7.45 (1H, dd, J = 9.1, 2.8 Hz), 8.02 (1H, d, J = 9.3 Hz), 8.06 (1H, dd, J = 8.4, 1.1 Hz), 8.78 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 1.42 (3H, t, J = 7.1 Hz), 4.05 (2H, q, J = 7.0 Hz), 5.16 (2H, s), 6.86-6.89 (1H, m), 7.03-7.05 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.28-7.36 (2H, m), 7.45 (1H, dd, J = 9.4, 2.8 Hz), 8.02 (1H, dd, J = 8.3, 1.5 Hz), 8.02 (1H, d, J = 9.0 Hz), 8.77 (1H, dd, J = 4.4, 1.7 Hz). Production Example 8
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.17 g of iodoethane and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature for 3 hours. 4% sodium hydroxide was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.24 g of [(3-ethoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 8).
Compound 8

¹ H-NMR (CDCl ₃ ) δ: 1.42 (3H, t, J = 7.1 Hz), 4.05 (2H, q, J = 7.0 Hz), 5.16 (2H, s), 6.86-6.89 (1H, m), 7.03-7.05 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.28-7.36 (2H, m), 7.45 (1H, dd, J = 9.4, 2.8 Hz), 8.02 (1H, dd, J = 8.3, 1.5 Hz), 8.02 (1H, d, J = 9.0 Hz), 8.77 (1H, dd, J = 4.4, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 1.04 (3H, t, J = 7.4 Hz), 1.77-1.86 (2H, m), 3.94 (2H, t, J = 6.6 Hz), 5.16 (2H, s), 6.89 (1H, d, J = 8.3 Hz), 7.03-7.05 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.26-7.36 (2H, m), 7.46 (1H, dd, J = 9.1, 2.8 Hz), 8.01-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz). Production Example 9
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.20 g of 1-iodopropane and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature for 4 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.23 g of [(3-propoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 9).
Compound 9

¹ H-NMR (CDCl ₃ ) δ: 1.04 (3H, t, J = 7.4 Hz), 1.77-1.86 (2H, m), 3.94 (2H, t, J = 6.6 Hz), 5.16 (2H, s), 6.89 (1H, d, J = 8.3 Hz), 7.03-7.05 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.26-7.36 (2H, m), 7.46 (1H, dd, J = 9.1, 2.8 Hz), 8.01-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 0.97 (3H, t, J = 7.4 Hz), 1.45-1.54 (2H, m), 1.73-1.83 (2H, m), 3.98 (2H, t, J = 6.6 Hz), 5.15 (2H, s), 6.86-6.89 (1H, m), 7.02-7.05 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.28-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.04 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz). Production Example 10
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.16 g of 1-bromobutane and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature for 5 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.23 g of [(3-butoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 10).
Compound 10

¹ H-NMR (CDCl ₃ ) δ: 0.97 (3H, t, J = 7.4 Hz), 1.45-1.54 (2H, m), 1.73-1.83 (2H, m), 3.98 (2H, t, J = 6.6 Hz ), 5.15 (2H, s), 6.86-6.89 (1H, m), 7.02-7.05 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.28-7.36 (2H, m), 7.46 ( 1H, dd, J = 9.3, 2.7 Hz), 8.00-8.04 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 0.90-0.95 (3H, m), 1.36-1.48 (4H, m), 1.76-1.83 (2H, m), 3.98 (2H, t, J = 6.6 Hz), 5.16 (2H, s), 6.88 (1H, dd, J = 7.2, 2.1 Hz), 7.01-7.05 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.26-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.05 (2H, m), 8.78 (1H, dd, J = 4.1, 1.7 Hz). Production Example 11
To a mixed solution of 0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.21 g of 1-iodopentane and 3 ml of DMF, 0.39 g of cesium carbonate was added and stirred at room temperature for 5 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.24 g of [(3-pentynyloxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 11).
Compound 11

¹ H-NMR (CDCl ₃ ) δ: 0.90-0.95 (3H, m), 1.36-1.48 (4H, m), 1.76-1.83 (2H, m), 3.98 (2H, t, J = 6.6 Hz), 5.16 (2H, s), 6.88 (1H, dd, J = 7.2, 2.1 Hz), 7.01-7.05 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.26-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.05 (2H, m), 8.78 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 2.50 (1H, t, J = 2.4 Hz), 4.72 (2H, d, J = 2.4 Hz), 5.18 (2H, s), 6.96 (1H, dd, J = 8.2, 2.6 Hz), 7.10-7.12 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.33-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.02 (1H, d, J = 9.0 Hz), 8.03 (1H, d, J = 6.6 Hz), 8.77 (1H, dd, J = 4.3, 1.6 Hz). Production Example 12
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.14 g of propargyl bromide and 0.39 g of cesium carbonate were added to 3 ml of DMF and stirred overnight at room temperature. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.24 g of {[3- (2-propynyloxyphenyl)] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 12). It was.
Compound 12

¹ H-NMR (CDCl ₃ ) δ: 2.50 (1H, t, J = 2.4 Hz), 4.72 (2H, d, J = 2.4 Hz), 5.18 (2H, s), 6.96 (1H, dd, J = 8.2 , 2.6 Hz), 7.10-7.12 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.33-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.02 (1H, d, J = 9.0 Hz), 8.03 (1H, d, J = 6.6 Hz), 8.77 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 1.97 (1H, t, J = 2.6 Hz), 2.02 (2H, q, J = 6.6 Hz), 2.42 (2H, td, J = 7.0, 2.7 Hz), 4.09 (2H, t, J = 6.0 Hz), 5.16 (2H, s), 6.87-6.91 (1H, m), 7.04-7.07 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.30-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz). Production Example 13
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.12 g of 5-chloro-1-pentyne and 0.39 g of cesium carbonate are added to 3 ml of DMF, stirred overnight at room temperature, and then at 80 ° C. for 7 hours. Stir. A 4% aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.31 g of {[3- (4-pentynyloxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 13) was added. Obtained.
Compound 13

¹ H-NMR (CDCl ₃ ) δ: 1.97 (1H, t, J = 2.6 Hz), 2.02 (2H, q, J = 6.6 Hz), 2.42 (2H, td, J = 7.0, 2.7 Hz), 4.09 ( 2H, t, J = 6.0 Hz), 5.16 (2H, s), 6.87-6.91 (1H, m), 7.04-7.07 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.30-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 1.74 (2H, dd, J = 14.8, 7.4 Hz), 1.88-1.98 (3H, m), 2.28 (2H, td, J = 7.0, 2.6 Hz), 4.01 (2H, t, J = 6.2 Hz), 5.16 (2H, s), 6.88 (1H, d, J = 8.3 Hz), 7.05 (2H, d, J = 8.3 Hz), 7.14 (1H, d, J = 2.4 Hz), 7.29-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.01-8.04 (2H, m), 8.78 (1H, s). Production Example 14
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.14 g of 6-chloro-1-hexyne and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at 80 ° C. for 8 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.32 g of {[3- (5-hexynyloxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 14). .
Compound 14

¹ H-NMR (CDCl ₃ ) δ: 1.74 (2H, dd, J = 14.8, 7.4 Hz), 1.88-1.98 (3H, m), 2.28 (2H, td, J = 7.0, 2.6 Hz), 4.01 (2H , t, J = 6.2 Hz), 5.16 (2H, s), 6.88 (1H, d, J = 8.3 Hz), 7.05 (2H, d, J = 8.3 Hz), 7.14 (1H, d, J = 2.4 Hz ), 7.29-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.01-8.04 (2H, m), 8.78 (1H, s).

¹H-NMR (CDCl₃) δ: 1.84 (3H, t, J = 2.3 Hz), 4.67 (2H, q, J = 2.2 Hz), 5.17 (2H, s), 6.95 (1H, dd, J = 7.6, 2.0 Hz), 7.08-7.10 (2H, m), 7.14 (1H, d, J = 2.9 Hz), 7.31-7.36 (2H, m), 7.45 (1H, dd, J = 9.3, 2.7 Hz), 8.02 (1H, d, J = 9.0 Hz), 8.03 (1H, d, J = 6.8 Hz), 8.77 (1H, dd, J = 4.1, 1.7 Hz). Production Example 15
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.16 g of 4-bromo-2-butyne and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature for 4 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.26 g of {[3- (2-butynyloxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 15). .
Compound 15

¹ H-NMR (CDCl ₃ ) δ: 1.84 (3H, t, J = 2.3 Hz), 4.67 (2H, q, J = 2.2 Hz), 5.17 (2H, s), 6.95 (1H, dd, J = 7.6 , 2.0 Hz), 7.08-7.10 (2H, m), 7.14 (1H, d, J = 2.9 Hz), 7.31-7.36 (2H, m), 7.45 (1H, dd, J = 9.3, 2.7 Hz), 8.02 (1H, d, J = 9.0 Hz), 8.03 (1H, d, J = 6.8 Hz), 8.77 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 1.12 (3H, t, J = 7.4 Hz), 2.18-2.25 (2H, m), 4.69 (2H, t, J = 2.2 Hz), 5.17 (2H, s), 6.95 (1H, dd, J = 8.2, 2.3 Hz), 7.07-7.11 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.31-7.36 (2H, m), 7.45 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.04 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz). Production Example 16
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.17 g of 1-bromo-2-pentyne and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature for 5 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.25 g of {[3- (2-pentynyloxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 16) was obtained. Obtained.
Compound 16

¹ H-NMR (CDCl ₃ ) δ: 1.12 (3H, t, J = 7.4 Hz), 2.18-2.25 (2H, m), 4.69 (2H, t, J = 2.2 Hz), 5.17 (2H, s), 6.95 (1H, dd, J = 8.2, 2.3 Hz), 7.07-7.11 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.31-7.36 (2H, m), 7.45 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.04 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 4.55-4.57 (2H, m), 5.16 (2H, s), 5.27-5.30 (1H, m), 5.39-5.44 (1H, m), 6.01-6.11 (1H, m), 6.90 (1H, dd, J = 7.8, 2.0 Hz), 7.05-7.07 (2H, m), 7.14 (1H, d, J = 2.9 Hz), 7.29-7.36 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.02 (1H, d, J = 9.3 Hz), 8.03 (1H, dd, J = 8.0, 1.5 Hz), 8.77 (1H, dd, J = 4.3, 1.6 Hz). Production Example 17
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.14 g of 3-bromo-1-propene and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature for 4 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.24 g of {[3- (2-propenyloxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 17). It was.
Compound 17

¹ H-NMR (CDCl ₃ ) δ: 4.55-4.57 (2H, m), 5.16 (2H, s), 5.27-5.30 (1H, m), 5.39-5.44 (1H, m), 6.01-6.11 (1H, m), 6.90 (1H, dd, J = 7.8, 2.0 Hz), 7.05-7.07 (2H, m), 7.14 (1H, d, J = 2.9 Hz), 7.29-7.36 (2H, m), 7.46 (1H , dd, J = 9.3, 2.7 Hz), 8.02 (1H, d, J = 9.3 Hz), 8.03 (1H, dd, J = 8.0, 1.5 Hz), 8.77 (1H, dd, J = 4.3, 1.6 Hz) .

¹H-NMR (CDCl₃) δ: 1.86-1.92 (2H, m), 2.21-2.28 (2H, m), 3.99 (2H, t, J = 6.5 Hz), 4.98-5.02 (1H, m), 5.04-5.09 (1H, m), 5.16 (2H, s), 5.80-5.90 (1H, m), 6.86-6.89 (1H, m), 7.03-7.06 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.46 (1H, dd, J = 9.1, 2.8 Hz), 8.02 (1H, d, J = 9.3 Hz), 8.03 (1H, dd, J = 7.8, 1.7 Hz), 8.77 (1H, dd, J = 4.4, 1.7 Hz). Production Example 18
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.17 g of 5-bromo-1-pentene and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature for 10 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.28 g of {[3- (4-pentenyloxy) phenyl] methyl} quinolin-6-yl) ether (hereinafter referred to as the present compound 18). .
Compound 18

¹ H-NMR (CDCl ₃ ) δ: 1.86-1.92 (2H, m), 2.21-2.28 (2H, m), 3.99 (2H, t, J = 6.5 Hz), 4.98-5.02 (1H, m), 5.04 -5.09 (1H, m), 5.16 (2H, s), 5.80-5.90 (1H, m), 6.86-6.89 (1H, m), 7.03-7.06 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.46 (1H, dd, J = 9.1, 2.8 Hz), 8.02 (1H, d, J = 9.3 Hz), 8.03 (1H, dd, J = 7.8, 1.7 Hz), 8.77 (1H, dd, J = 4.4, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 1.54-1.62 (2H, m), 1.77-1.84 (2H, m), 2.10-2.16 (2H, m), 3.98 (2H, t, J = 6.5 Hz), 4.95-4.99 (1H, m), 5.01-5.06 (1H, m), 5.16 (2H, s), 5.78-5.88 (1H, m), 6.86-6.90 (1H, m), 7.02-7.06 (2H, m), 7.14-7.16 (1H, m), 7.26-7.37 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz). Production Example 19
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.19 g of 6-bromo-1-hexene and 0.39 g of cesium carbonate were added to 3 ml of DMF and stirred overnight at room temperature. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.32 g of {[3- (5-hexenyloxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 19). It was.
Compound 19

¹ H-NMR (CDCl ₃ ) δ: 1.54-1.62 (2H, m), 1.77-1.84 (2H, m), 2.10-2.16 (2H, m), 3.98 (2H, t, J = 6.5 Hz), 4.95 -4.99 (1H, m), 5.01-5.06 (1H, m), 5.16 (2H, s), 5.78-5.88 (1H, m), 6.86-6.90 (1H, m), 7.02-7.06 (2H, m) , 7.14-7.16 (1H, m), 7.26-7.37 (2H, m), 7.46 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 1.75 (3H, dd, J = 6.2, 1.3 Hz), 4.48 (2H, d, J = 6.1 Hz), 5.16 (2H, s), 5.68-5.78 (1H, m), 5.80-5.95 (1H, m), 6.88-6.90 (1H, m), 7.04-7.06 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.45 (1H, dd, J = 9.3, 2.7 Hz), 8.02 (1H, d, J = 9.0 Hz), 8.03 (1H, d, J = 8.3 Hz), 8.77 (1H, dd, J = 4.1, 1.7 Hz). Production Example 20
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.16 g of 4-bromo-2-butene and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature overnight. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.14 g of {[3- (2-butenyloxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 20). .
Compound 20

¹ H-NMR (CDCl ₃ ) δ: 1.75 (3H, dd, J = 6.2, 1.3 Hz), 4.48 (2H, d, J = 6.1 Hz), 5.16 (2H, s), 5.68-5.78 (1H, m ), 5.80-5.95 (1H, m), 6.88-6.90 (1H, m), 7.04-7.06 (2H, m), 7.14 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.45 (1H, dd, J = 9.3, 2.7 Hz), 8.02 (1H, d, J = 9.0 Hz), 8.03 (1H, d, J = 8.3 Hz), 8.77 (1H, dd, J = 4.1, 1.7 Hz) ).

¹H-NMR (CDCl₃) δ: 0.98-1.04 (3.0H, m), 2.04-2.19 (2.0H, m), 4.49 (1.2H, d, J = 5.9 Hz), 4.60 (0.8H, d, J = 5.1 Hz), 5.14-5.17 (2.0H, m), 5.62-5.73 (1.2H, m), 5.79-5.93 (0.8H, m), 6.89 (1.0H, dd, J = 8.2, 2.3 Hz), 7.03-7.07 (2.0H, m), 7.14 (1.0H, d, J = 2.4 Hz), 7.28-7.36 (2.0H, m), 7.45 (1.0H, dd, J = 9.3, 2.9 Hz), 8.00-8.05 (2.0H, m), 8.77 (1.0H, dd, J = 4.3, 1.6 Hz). Production Example 21
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.17 g of 1-bromo-3-pentene and 0.39 g of cesium carbonate were added to 3 ml of DMF and stirred at room temperature overnight. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.14 g of {[3- (2-pentenyloxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 21). It was.
Compound 21

¹ H-NMR (CDCl ₃ ) δ: 0.98-1.04 (3.0H, m), 2.04-2.19 (2.0H, m), 4.49 (1.2H, d, J = 5.9 Hz), 4.60 (0.8H, d, J = 5.1 Hz), 5.14-5.17 (2.0H, m), 5.62-5.73 (1.2H, m), 5.79-5.93 (0.8H, m), 6.89 (1.0H, dd, J = 8.2, 2.3 Hz) , 7.03-7.07 (2.0H, m), 7.14 (1.0H, d, J = 2.4 Hz), 7.28-7.36 (2.0H, m), 7.45 (1.0H, dd, J = 9.3, 2.9 Hz), 8.00 -8.05 (2.0H, m), 8.77 (1.0H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 3.45 (3H, s), 3.75-3.77 (2H, m), 4.14 (2H, t, J = 4.8 Hz), 5.16 (2H, s), 6.90-6.92 (1H, m), 7.05-7.07 (2H, m), 7.13 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.45 (1H, dd, J = 9.4, 2.8 Hz), 8.02 (1H, d, J = 9.3 Hz), 8.77 (1H, dd, J = 4.3, 1.6 Hz), 8.03 (1H, d, J = 8.5 Hz). Production Example 22
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.16 g of 1-bromo-2-methoxyethane and 0.39 g of cesium carbonate are added to 3 ml of DMF, stirred at room temperature for 2 hours and then at 80 ° C. Stir for 3 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.17 g of {[3- (2-methoxyethoxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 22). It was.
Compound 22

¹ H-NMR (CDCl ₃ ) δ: 3.45 (3H, s), 3.75-3.77 (2H, m), 4.14 (2H, t, J = 4.8 Hz), 5.16 (2H, s), 6.90-6.92 (1H , m), 7.05-7.07 (2H, m), 7.13 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.45 (1H, dd, J = 9.4, 2.8 Hz), 8.02 ( 1H, d, J = 9.3 Hz), 8.77 (1H, dd, J = 4.3, 1.6 Hz), 8.03 (1H, d, J = 8.5 Hz).

¹H-NMR (CDCl₃) δ: 2.02-2.09 (2H, m), 3.35 (3H, s), 3.56 (2H, t, J = 6.1 Hz), 4.08 (2H, t, J = 6.2 Hz), 5.16 (2H, s), 6.89 (1H, dd, J = 7.9, 2.1 Hz), 7.04-7.06 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.46 (1H, dd, J = 9.4, 2.8 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz). Production Example 23
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.18 g of 1-bromo-3-methoxypropane and 0.39 g of cesium carbonate were added to 3 ml of DMF and stirred overnight at room temperature. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.075 g of {[3- (3-methoxypropoxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 23). It was.
Compound 23

¹ H-NMR (CDCl ₃ ) δ: 2.02-2.09 (2H, m), 3.35 (3H, s), 3.56 (2H, t, J = 6.1 Hz), 4.08 (2H, t, J = 6.2 Hz), 5.16 (2H, s), 6.89 (1H, dd, J = 7.9, 2.1 Hz), 7.04-7.06 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m) , 7.46 (1H, dd, J = 9.4, 2.8 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 1.71-1.79 (2H, m), 1.83-1.90 (2H, m), 3.34 (3H, s), 3.44 (2H, t, J = 6.3 Hz), 4.01 (2H, t, J = 6.2 Hz), 5.16 (2H, s), 6.88 (1H, dd, J = 8.0, 2.0 Hz), 7.02-7.06 (2H, m), 7.15 (1H, d, J = 2.7 Hz), 7.28-7.36 (2H, m), 7.46 (1H, dd, J = 9.4, 2.8 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz). Production Example 24
Add 0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.18 g of 4-methoxybutyl methanesulfonate and 0.39 g of cesium carbonate to 3 ml of DMF, stir at room temperature overnight, and then stir at 80 ° C. for 4 hours. did. A 4% aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.21 g of {[3- (4-methoxybutoxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 24). It was.
Compound 24

¹ H-NMR (CDCl ₃ ) δ: 1.71-1.79 (2H, m), 1.83-1.90 (2H, m), 3.34 (3H, s), 3.44 (2H, t, J = 6.3 Hz), 4.01 (2H , t, J = 6.2 Hz), 5.16 (2H, s), 6.88 (1H, dd, J = 8.0, 2.0 Hz), 7.02-7.06 (2H, m), 7.15 (1H, d, J = 2.7 Hz) , 7.28-7.36 (2H, m), 7.46 (1H, dd, J = 9.4, 2.8 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 1.24 (3H, t, J = 7.1 Hz), 3.60 (2H, q, J = 7.0 Hz), 3.78-3.81 (2H, m), 4.14 (2H, t, J = 4.9 Hz), 5.16 (2H, s), 6.91 (1H, dd, J = 8.3, 2.4 Hz), 7.04-7.08 (2H, m), 7.13 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.45 (1H, dd, J = 9.3, 2.9 Hz), 8.00-8.04 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz). Production Example 25
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.18 g of 1-bromo-2-ethoxyethane and 0.39 g of cesium carbonate are added to 3 ml of DMF and stirred at room temperature overnight, then at 80 ° C. for 2 hours. Stir for hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.10 g of {[3- (2-ethoxyethoxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 25). It was.
Compound 25

¹ H-NMR (CDCl ₃ ) δ: 1.24 (3H, t, J = 7.1 Hz), 3.60 (2H, q, J = 7.0 Hz), 3.78-3.81 (2H, m), 4.14 (2H, t, J = 4.9 Hz), 5.16 (2H, s), 6.91 (1H, dd, J = 8.3, 2.4 Hz), 7.04-7.08 (2H, m), 7.13 (1H, d, J = 2.7 Hz), 7.29-7.36 (2H, m), 7.45 (1H, dd, J = 9.3, 2.9 Hz), 8.00-8.04 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 1.20 (3H, t, J = 7.0 Hz), 2.03-2.09 (2H, m), 3.47-3.53 (2H, m), 3.60 (2H, t, J = 6.2 Hz), 4.09 (2H, t, J = 6.2 Hz), 5.16 (2H, s), 6.89 (1H, dd, J = 8.2, 2.3 Hz), 7.04-7.05 (2H, m), 7.15 (1H, d, J = 2.4 Hz), 7.29-7.36 (2H, m), 7.46 (1H, dd, J = 9.1, 2.8 Hz), 8.01-8.05 (2H, m), 8.77 (1H, dd, J = 4.1, 1.5 Hz). Production Example 26
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.21 g of 3-ethoxypropyl methanesulfonate and 0.39 g of cesium carbonate are added to 3 ml of DMF, stirred at room temperature for 2 hours, and then at 80 ° C. for 2 hours. Stir. A 4% aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.17 g of {[3- (3-ethoxypropoxy) phenyl] methyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 26). It was.
Compound 26

¹ H-NMR (CDCl ₃ ) δ: 1.20 (3H, t, J = 7.0 Hz), 2.03-2.09 (2H, m), 3.47-3.53 (2H, m), 3.60 (2H, t, J = 6.2 Hz ), 4.09 (2H, t, J = 6.2 Hz), 5.16 (2H, s), 6.89 (1H, dd, J = 8.2, 2.3 Hz), 7.04-7.05 (2H, m), 7.15 (1H, d, J = 2.4 Hz), 7.29-7.36 (2H, m), 7.46 (1H, dd, J = 9.1, 2.8 Hz), 8.01-8.05 (2H, m), 8.77 (1H, dd, J = 4.1, 1.5 Hz ).

¹H-NMR (CDCl₃) δ: 5.08 (2H, s), 5.16 (2H, s), 6.96 (1H, dd, J = 8.2, 2.6 Hz), 7.07 (1H, d, J = 7.6 Hz), 7.11-7.14 (2H, m), 7.29-7.39 (5H, m), 7.42-7.46 (3H, m), 8.01-8.03 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz). Production Example 27
0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.20 g of benzyl bromide and 0.39 g of cesium carbonate were added to 3 ml of DMF, and the mixture was stirred at room temperature for 2 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.29 g of [(3-benzyloxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 27).
Compound 27

¹ H-NMR (CDCl ₃ ) δ: 5.08 (2H, s), 5.16 (2H, s), 6.96 (1H, dd, J = 8.2, 2.6 Hz), 7.07 (1H, d, J = 7.6 Hz), 7.11-7.14 (2H, m), 7.29-7.39 (5H, m), 7.42-7.46 (3H, m), 8.01-8.03 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 5.17 (2H, s) , 6.97-7.03 (3H), 7.10-7.14 (3H), 7.22 (1H, d, J = 7.6 Hz), 7.31-7.39 (4H), 7.43 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.04 (2H), 8.77-8.79 (1H, m). Production Example 28
To a mixture of 0.29 g of quinolin-6-ol, 0.44 g of 3-phenoxybenzyl chloride and 5 ml of DMF, 0.09 g of sodium hydride (55% oil dispersion) was added while cooling with ice in a nitrogen atmosphere, and at room temperature. Stir for 4 hours. Ice and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine (3 times), dried, and concentrated under reduced pressure. 0.73 g of the obtained residue was subjected to silica gel column chromatography to obtain 0.56 g of [(3-phenoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 28).
Compound 28

¹ H-NMR (CDCl ₃ ) δ: 5.17 (2H, s), 6.97-7.03 (3H), 7.10-7.14 (3H), 7.22 (1H, d, J = 7.6 Hz), 7.31-7.39 (4H), 7.43 (1H, dd, J = 9.3, 2.7 Hz), 8.00-8.04 (2H), 8.77-8.79 (1H, m).

本化合物２９
¹H-NMR (CDCl₃) δ: 5.15 (2H, s), 7.07-7.13 (2H, m), 7.14 (1H, d, J = 2.9 Hz), 7.36 (1H, dd, J = 8.3, 4.1 Hz), 7.43-7.48 (3H, m), 8.01-8.05 (2H, m), 8.78 (1H, dd, J = 4.1, 1.7 Hz). Production Example 29
To a mixed solution of 0.096 g of 55% sodium hydride (oil) and 3 ml of DMF, a mixed solution of 0.29 g of quinolin-6-ol, 0.28 g of 4-fluorobenzyl chlorad and 2 ml of DMF was added under ice cooling. Water was added to the reaction mixture stirred overnight at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.40 g of [(4-fluorophenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 29).

Compound 29
¹ H-NMR (CDCl ₃ ) δ: 5.15 (2H, s), 7.07-7.13 (2H, m), 7.14 (1H, d, J = 2.9 Hz), 7.36 (1H, dd, J = 8.3, 4.1 Hz ), 7.43-7.48 (3H, m), 8.01-8.05 (2H, m), 8.78 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 2.38 (3H, s), 5.15 (2H, s), 7.15 (1H, d, J = 2.7 Hz), 7.22 (2H, d, J = 7.8 Hz), 7.33-7.39 (3H, m), 7.44 (1H, dd, J = 9.0, 2.7 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz). Production Example 30
To a mixed solution of 0.096 g of 55% sodium hydride (oil) and 3 ml of DMF, a mixed solution of 0.29 g of quinolin-6-ol, 0.37 g of 4-methylbenzyl bromide and 2 ml of DMF was added under ice cooling. Water was added to the reaction mixture stirred overnight at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.34 g of [(4-methylphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 30).
Compound 30

¹ H-NMR (CDCl ₃ ) δ: 2.38 (3H, s), 5.15 (2H, s), 7.15 (1H, d, J = 2.7 Hz), 7.22 (2H, d, J = 7.8 Hz), 7.33- 7.39 (3H, m), 7.44 (1H, dd, J = 9.0, 2.7 Hz), 8.00-8.05 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 3.83 (3H, s) , 5.12 (2H, s) , 6.95 (2H, d, J = 8.4 Hz), 7.16 (1H, d, J = 2.7 Hz), 7.34-7.37 (1H, m), 7.42 (2H, d, J = 8.4 Hz), 7.44 (1H, m), 8.00-8.05 (2H), 8.77 (1H, d, J = 4.1 Hz). Production Example 31
To a mixture of 0.29 g of quinolin-6-ol, 0.31 g of 4-methoxybenzyl chloride and 5 ml of DMF, 0.09 g of sodium hydride (55% oil dispersion) was added while cooling with ice in a nitrogen atmosphere, and at room temperature. Stir for 4 hours. Ice and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine (3 times), dried, and concentrated under reduced pressure. 0.62 g of the obtained residue was subjected to silica gel column chromatography to obtain 0.49 g of [(4-methoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 6).
Compound 31

¹ H-NMR (CDCl ₃ ) δ: 3.83 (3H, s), 5.12 (2H, s), 6.95 (2H, d, J = 8.4 Hz), 7.16 (1H, d, J = 2.7 Hz), 7.34- 7.37 (1H, m), 7.42 (2H, d, J = 8.4 Hz), 7.44 (1H, m), 8.00-8.05 (2H), 8.77 (1H, d, J = 4.1 Hz).

¹H-NMR (CDCl₃) δ: 5.15 (2H, s), 7.03-7.06 (4H, m), 7.12 (1H, t, J = 7.4 Hz), 7.17 (1H, d, J = 2.9 Hz), 7.33-7.38 (3H, m), 7.44-7.46 (3H, m), 8.01-8.06 (2H, m), 8.78 (1H, dd, J = 4.3, 1.6 Hz). Production Example 32
To a mixed solution of 55% sodium hydride (oil) 0.096 g and 3 ml of DMF, a mixed solution of 0.29 g of quinolin-6-ol, 0.55 g of (4-phenoxyphenyl) methyl-methanesulfonate and 2 ml of DMF was added under ice cooling. added. Water was added to the reaction mixture stirred at room temperature for 6 hours, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.38 g of [(4-phenoxyphenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 32).
Compound 32

¹ H-NMR (CDCl ₃ ) δ: 5.15 (2H, s), 7.03-7.06 (4H, m), 7.12 (1H, t, J = 7.4 Hz), 7.17 (1H, d, J = 2.9 Hz), 7.33-7.38 (3H, m), 7.44-7.46 (3H, m), 8.01-8.06 (2H, m), 8.78 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 5.25 (2H, s), 6.94-7.00 (2H, m), 7.26 (1H, d, J = 2.7 Hz), 7.32-7.42 (3H, m), 8.01 (1H, d, J = 9.3 Hz), 8.08 (1H, dd, J = 8.4, 1.1 Hz), 8.79 (1H, dd, J = 4.4, 1.7 Hz). Production Example 33
To a mixed solution of 0.096 g of 55% sodium hydride (oil) and 3 ml of DMF, a mixed solution of 0.29 g of quinolin-6-ol, 0.41 g of 2,6-difluorobenzyl bromide and 2 ml of DMF was added under ice cooling. Water was added to the reaction mixture stirred at room temperature for 2 hours, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.40 g of [(2,6-difluorophenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 33).
Compound 33

¹ H-NMR (CDCl ₃ ) δ: 5.25 (2H, s), 6.94-7.00 (2H, m), 7.26 (1H, d, J = 2.7 Hz), 7.32-7.42 (3H, m), 8.01 (1H , d, J = 9.3 Hz), 8.08 (1H, dd, J = 8.4, 1.1 Hz), 8.79 (1H, dd, J = 4.4, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 5.21 (2H, s), 6.86-6.96 (2H, m), 7.17 (1H, d, J = 2.7 Hz), 7.37 (1H, dd, J = 8.3, 4.1 Hz), 7.43 (1H, dd, J = 9.1, 2.8 Hz), 7.53 (1H, td, J = 8.4, 6.4 Hz), 8.03 (1H, d, J = 9.3 Hz), 8.06 (1H, dd, J = 8.5, 1.5 Hz), 8.79 (1H, dd, J = 4.3, 1.6 Hz). Production Example 34
To a mixed solution of 0.096 g of 55% sodium hydride (oil) and 3 ml of DMF, a mixed solution of 0.29 g of quinolin-6-ol, 0.41 g of 2,4-difluorobenzyl bromide and 2 ml of DMF was added under ice cooling. Water was added to the reaction mixture stirred overnight at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.44 g of [(2,4-difluorophenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 34).
Compound 34

¹ H-NMR (CDCl ₃ ) δ: 5.21 (2H, s), 6.86-6.96 (2H, m), 7.17 (1H, d, J = 2.7 Hz), 7.37 (1H, dd, J = 8.3, 4.1 Hz ), 7.43 (1H, dd, J = 9.1, 2.8 Hz), 7.53 (1H, td, J = 8.4, 6.4 Hz), 8.03 (1H, d, J = 9.3 Hz), 8.06 (1H, dd, J = 8.5, 1.5 Hz), 8.79 (1H, dd, J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 5.24 (2H, s), 6.98-7.04 (1H, m), 7.08 (1H, td, J = 9.0, 4.4 Hz), 7.17 (1H, d, J = 2.9 Hz), 7.27-7.32 (1H, m), 7.37 (1H, dd, J = 8.3, 4.2 Hz), 7.46 (1H, dd, J = 9.3, 2.8 Hz), 8.03-8.07 (2H, m), 8.80 (1H, dd, J = 4.3, 1.7 Hz). Production Example 35
Into a mixed solution of 0.096 g of 55% sodium hydride (oil) and 3 ml of DMF, a mixed solution of 0.29 g of quinolin-6-ol, 0.44 g of (2,5-difluorophenyl) methyl-methanesulfonate and 2 ml of DMF was ice-cooled. Added below. Water was added to the reaction mixture stirred at room temperature for 3 hours, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.39 g of [(2,5-difluorophenyl) methyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 35).
Compound 35

¹ H-NMR (CDCl ₃ ) δ: 5.24 (2H, s), 6.98-7.04 (1H, m), 7.08 (1H, td, J = 9.0, 4.4 Hz), 7.17 (1H, d, J = 2.9 Hz ), 7.27-7.32 (1H, m), 7.37 (1H, dd, J = 8.3, 4.2 Hz), 7.46 (1H, dd, J = 9.3, 2.8 Hz), 8.03-8.07 (2H, m), 8.80 ( (1H, dd, J = 4.3, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 3.18 (2H, t, J = 7.1 Hz), 4.29 (2H, t, J = 7.1 Hz), 7.05 (1H, d, J = 2.9 Hz), 7.23-7.35 (6H, m), 7.37 (1H, dd, J = 9.3, 2.7 Hz), 7.99 (1H, d, J = 9.0 Hz), 8.00 (1H, dd, J = 7.9, 1.6 Hz), 8.76 (1H, dd, J = 4.3, 1.6 Hz). Production Example 36
To a mixed solution of 0.29 g of quinolin-6-ol, 0.24 g of phenethyl alcohol, 0.62 g of triphenylphosphine, and 5 ml of tetrahydrofuran (hereinafter sometimes referred to as THF), diethyl azodicarboxylate (hereinafter referred to as DEAD). In some cases, 1.1 ml of (40% toluene solution) was added under ice cooling, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with 4% aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.29 g of (2-phenylethyl) (quinolin-6-yl) ether (hereinafter referred to as the present compound 36).
Compound 36

¹ H-NMR (CDCl ₃ ) δ: 3.18 (2H, t, J = 7.1 Hz), 4.29 (2H, t, J = 7.1 Hz), 7.05 (1H, d, J = 2.9 Hz), 7.23-7.35 ( 6H, m), 7.37 (1H, dd, J = 9.3, 2.7 Hz), 7.99 (1H, d, J = 9.0 Hz), 8.00 (1H, dd, J = 7.9, 1.6 Hz), 8.76 (1H, dd , J = 4.3, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 3.16 (2H, t, J = 7.1 Hz), 3.82 (3H, s), 4.29 (2H, t, J = 7.1 Hz), 6.81 (1H, dd, J = 8.2, 2.7 Hz), 6.87-6.92 (2H, m), 7.06 (1H, d, J = 2.7 Hz), 7.24-7.28 (1H, m), 7.34 (1H, dd, J = 8.3, 4.2 Hz), 7.38 (1H, dd, J = 9.3, 2.8 Hz), 7.98-8.02 (2H, m), 8.76 (1H, dd, J = 4.1, 1.7 Hz). Production Example 37
To a mixed solution of 0.29 g of quinolin-6-ol, 0.30 g of 2- (3-methoxyphenyl) ethanol, 0.62 g of triphenylphosphine and 5 ml of THF, 1.1 ml of DEAD (40% toluene solution) was cooled with ice. The mixture was further stirred at room temperature for 2 hours. A 4% aqueous sodium hydroxide solution was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with 4% aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.48 g of [2- (3-methoxyphenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 37).
Compound 37

¹ H-NMR (CDCl ₃ ) δ: 3.16 (2H, t, J = 7.1 Hz), 3.82 (3H, s), 4.29 (2H, t, J = 7.1 Hz), 6.81 (1H, dd, J = 8.2 , 2.7 Hz), 6.87-6.92 (2H, m), 7.06 (1H, d, J = 2.7 Hz), 7.24-7.28 (1H, m), 7.34 (1H, dd, J = 8.3, 4.2 Hz), 7.38 (1H, dd, J = 9.3, 2.8 Hz), 7.98-8.02 (2H, m), 8.76 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 3.15 (2H, t, J = 6.9 Hz), 4.29 (2H, t, J = 6.9 Hz), 6.90 (1H, dd, J = 8.0, 1.9 Hz), 6.99-7.13 (6H, m), 7.23-7.36 (5H, m), 7.97-8.02 (2H, m), 8.77 (1H, dd, J = 4.2, 1.3 Hz). Production Example 38
To a mixed solution of 0.21 g of quinolin-6-ol, 0.32 g of 2- (3-phenoxyphenyl) ethanol, 0.47 g of triphenylphosphine and 5 ml of THF, 0.45 g of 1,1 ′-(azodicarbonyl) dipiperidine is added. The mixture was added under ice cooling and stirred at room temperature overnight. A 4% aqueous sodium hydroxide solution was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with 4% aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.22 g of [2- (3-phenoxyphenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 38).
Compound 38

¹ H-NMR (CDCl ₃ ) δ: 3.15 (2H, t, J = 6.9 Hz), 4.29 (2H, t, J = 6.9 Hz), 6.90 (1H, dd, J = 8.0, 1.9 Hz), 6.99- 7.13 (6H, m), 7.23-7.36 (5H, m), 7.97-8.02 (2H, m), 8.77 (1H, dd, J = 4.2, 1.3 Hz).

¹H-NMR (CDCl₃) δ: 3.16 (2H, t, J = 7.0 Hz), 4.29 (2H, t, J = 7.0 Hz), 6.97-7.02 (4H, m), 7.06-7.12 (2H, m), 7.27-7.40 (6H, m), 7.98-8.03 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz). Production Example 39
To a mixed solution of 0.21 g of quinolin-6-ol, 0.32 g of 2- (4-phenoxyphenyl) ethanol, 0.47 g of triphenylphosphine and 5 ml of THF, 0.45 g of 1,1 ′-(azodicarbonyl) dipiperidine is added. The mixture was added under ice cooling and stirred at room temperature overnight. A 4% aqueous sodium hydroxide solution was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with 4% aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.11 g of [2- (4-phenoxyphenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 39).
Compound 39

¹ H-NMR (CDCl ₃ ) δ: 3.16 (2H, t, J = 7.0 Hz), 4.29 (2H, t, J = 7.0 Hz), 6.97-7.02 (4H, m), 7.06-7.12 (2H, m ), 7.27-7.40 (6H, m), 7.98-8.03 (2H, m), 8.77 (1H, dd, J = 4.1, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 3.12 (2H, t, J = 7.0 Hz), 4.26 (2H, t, J = 7.0 Hz), 5.06 (2H, s), 6.94-6.97 (2H, m), 7.06 (1H, d, J = 2.9 Hz), 7.23-7.26 (3H, m), 7.31-7.45 (6H, m), 7.98-8.03 (2H, m), 8.76 (1H, dd, J = 4.2, 1.3 Hz). Production Example 40
To a mixed solution of 0.26 g of 4- [2- (quinolin-6-yloxy) ethyl] phenol, 0.17 g of benzyl bromide and 3 ml of DMF, 0.39 g of cesium carbonate was added and stirred overnight at room temperature. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed successively with 15% aqueous sodium hydroxide, water and hexane, dried and [2- (4-benzyloxyphenyl) ethyl] (quinoline-6- Yl) ether (hereinafter referred to as the present compound 40) 0.18 g was obtained.
Compound 40

¹ H-NMR (CDCl ₃ ) δ: 3.12 (2H, t, J = 7.0 Hz), 4.26 (2H, t, J = 7.0 Hz), 5.06 (2H, s), 6.94-6.97 (2H, m), 7.06 (1H, d, J = 2.9 Hz), 7.23-7.26 (3H, m), 7.31-7.45 (6H, m), 7.98-8.03 (2H, m), 8.76 (1H, dd, J = 4.2, 1.3 Hz).

1H-NMR (CDCl3) δ: 2.37 (3H, s), 3.14 (2H, t, J = 7.2 Hz), 4.20 (2H, t, J = 7.2 Hz), 6.98 (1H, d, J = 2.7 Hz), 7.15-7.18 (3H, m), 7.22-7.27 (2H, m), 7.34 (1H, dd, J = 9.3, 2.8 Hz), 7.92 (1H, d, J = 7.0 Hz), 7.99 (1H, d, J = 9.2 Hz), 8.71 (1H, dd, J = 4.3, 1.7 Hz). Production Example 42
To a mixed solution of 0.29 g of quinolin-6-ol, 0.27 g of 2- (2-methylphenyl) ethanol, 0.62 g of triphenylphosphine and 5 ml of THF, 1.1 ml of DEAD (40% toluene solution) was cooled under ice cooling. The mixture was further stirred at room temperature for 3 hours. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.19 g of [2- (2-methylphenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 42).
Compound 42

1H-NMR (CDCl3) δ: 2.37 (3H, s), 3.14 (2H, t, J = 7.2 Hz), 4.20 (2H, t, J = 7.2 Hz), 6.98 (1H, d, J = 2.7 Hz) , 7.15-7.18 (3H, m), 7.22-7.27 (2H, m), 7.34 (1H, dd, J = 9.3, 2.8 Hz), 7.92 (1H, d, J = 7.0 Hz), 7.99 (1H, d , J = 9.2 Hz), 8.71 (1H, dd, J = 4.3, 1.7 Hz).

1H-NMR (CDCl3) δ: 3.20 (2H, t, J = 7.0 Hz), 4.27 (2H, t, J = 7.0 Hz), 7.02-7.12 (3H, m), 7.19-7.25 (1H, m), 7.27-7.36 (3H, m), 7.97-8.00 (2H, m), 8.74 (1H, d, J = 3.4 Hz). Production Example 43
To a mixed solution of 0.29 g of quinolin-6-ol, 0.28 g of 2- (2-fluorophenyl) ethanol, 0.62 g of triphenylphosphine and 5 ml of THF, 1.1 ml of DEAD (40% toluene solution) was cooled with ice. The mixture was further stirred at room temperature for 3 hours. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.16 g of [2- (2-fluorophenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 43).
Compound 43

1H-NMR (CDCl3) δ: 3.20 (2H, t, J = 7.0 Hz), 4.27 (2H, t, J = 7.0 Hz), 7.02-7.12 (3H, m), 7.19-7.25 (1H, m), 7.27-7.36 (3H, m), 7.97-8.00 (2H, m), 8.74 (1H, d, J = 3.4 Hz).

1H-NMR (CDCl3) δ: 3.18 (2H, t, J = 7.3 Hz), 3.83 (3H, s), 4.25 (2H, t, J = 7.3 Hz), 6.85-6.93 (2H, m), 7.06 (1H, d, J = 2.4 Hz), 7.21-7.30 (3H, m), 7.33-7.39 (1H, m), 7.94-7.99 (2H, m), 8.72 (1H, dd, J = 4.0, 1.6 Hz). Production Example 44
To a mixed solution of 0.29 g of quinolin-6-ol, 0.30 g of 2- (2-methoxyphenyl) ethanol, 0.62 g of triphenylphosphine and 5 ml of THF, 1.1 ml of DEAD (40% toluene solution) was cooled with ice. The mixture was further stirred at room temperature for 3 hours. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.15 g of [2- (2-methoxyphenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 44).
Compound 44

1H-NMR (CDCl3) δ: 3.18 (2H, t, J = 7.3 Hz), 3.83 (3H, s), 4.25 (2H, t, J = 7.3 Hz), 6.85-6.93 (2H, m), 7.06 ( 1H, d, J = 2.4 Hz), 7.21-7.30 (3H, m), 7.33-7.39 (1H, m), 7.94-7.99 (2H, m), 8.72 (1H, dd, J = 4.0, 1.6 Hz) .

1H-NMR (CDCl3) δ: 2.36 (3H, s), 3.14 (2H, t, J = 7.2 Hz), 4.28 (2H, t, J = 7.2 Hz), 7.06-7.13 (4H, m), 7.21-7.25 (1H, m), 7.32-7.40 (2H, m), 7.98-8.03 (2H, m), 8.76 (1H, dd, J = 4.4, 1.7 Hz). Production Example 45
To a mixed solution of 0.29 g of quinolin-6-ol, 0.28 g of 2- (3-methylphenyl) ethanol, 0.62 g of triphenylphosphine and 5 ml of THF, 1.1 ml of DEAD (40% toluene solution) was cooled with ice. The mixture was further stirred at room temperature for 3 hours. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.37 g of [2- (3-methylphenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 45).
Compound 45

1H-NMR (CDCl3) δ: 2.36 (3H, s), 3.14 (2H, t, J = 7.2 Hz), 4.28 (2H, t, J = 7.2 Hz), 7.06-7.13 (4H, m), 7.21- 7.25 (1H, m), 7.32-7.40 (2H, m), 7.98-8.03 (2H, m), 8.76 (1H, dd, J = 4.4, 1.7 Hz).

1H-NMR (CDCl3) δ: 3.13 (2H, t, J = 6.8 Hz), 4.25 (2H, t, J = 6.8 Hz), 6.90-6.96 (1H, m), 7.00-7.04 (2H, m), 7.07 (1H, d, J = 7.6 Hz), 7.24-7.36 (3H, m), 7.96-8.01 (2H, m), 8.74 (1H, dd, J = 4.3, 1.6 Hz). Production Example 46
To a mixed solution of 0.29 g of quinolin-6-ol, 0.27 g of 2- (3-fluorophenyl) ethanol, 0.62 g of triphenylphosphine and 5 ml of THF, 1.1 ml of DEAD (40% toluene solution) was cooled under ice cooling. The mixture was further stirred at room temperature for 3 hours. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.12 g of [2- (3-fluorophenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 46).
Compound 46

1H-NMR (CDCl3) δ: 3.13 (2H, t, J = 6.8 Hz), 4.25 (2H, t, J = 6.8 Hz), 6.90-6.96 (1H, m), 7.00-7.04 (2H, m), 7.07 (1H, d, J = 7.6 Hz), 7.24-7.36 (3H, m), 7.96-8.01 (2H, m), 8.74 (1H, dd, J = 4.3, 1.6 Hz).

1H-NMR (CDCl3) δ: 2.29 (3H, s), 3.06 (2H, t, J = 7.1 Hz), 4.16 (2H, t, J = 7.2 Hz), 6.94 (1H, d, J = 2.7 Hz), 7.10 (2H, d, J = 7.8 Hz), 7.16 (2H, d, J = 8.0 Hz), 7.19-7.23 (1H, m), 7.32 (1H, dd, J = 9.1, 2.8 Hz), 7.88 (1H, d, J = 7.1 Hz), 7.98 (1H, d, J = 9.3 Hz), 8.69 (1H, dd, J = 4.4, 1.7 Hz). Production Example 47
To a mixed solution of 0.29 g of quinolin-6-ol, 0.27 g of 2- (4-methylphenyl) ethanol, 0.62 g of triphenylphosphine and 5 ml of THF, 1.1 ml of DEAD (40% toluene solution) was cooled with ice. The mixture was further stirred at room temperature for 3 hours. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.29 g of [2- (4-methylphenyl) ethyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 47).
Compound 47

1H-NMR (CDCl3) δ: 2.29 (3H, s), 3.06 (2H, t, J = 7.1 Hz), 4.16 (2H, t, J = 7.2 Hz), 6.94 (1H, d, J = 2.7 Hz) , 7.10 (2H, d, J = 7.8 Hz), 7.16 (2H, d, J = 8.0 Hz), 7.19-7.23 (1H, m), 7.32 (1H, dd, J = 9.1, 2.8 Hz), 7.88 ( 1H, d, J = 7.1 Hz), 7.98 (1H, d, J = 9.3 Hz), 8.69 (1H, dd, J = 4.4, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 3.12 (2H, t, J = 6.9 Hz), 4.23 (2H, t, J = 6.9 Hz), 6.95-7.02 (4H, m), 7.07-7.13 (2H, m), 7.25-7.27 (2H, m), 7.30-7.35 (2H, m), 7.38 (1H, d, J = 2.4 Hz), 7.97-8.01 (1H, m), 8.80 (1H, s). Production Example 48
In a mixed solution of benzothiazol-6-ol 0.15 g, 2- (4-phenoxyphenyl) ethanol 0.21 g, triphenylphosphine 0.31 g and THF 5 ml, DEAD (40% toluene solution) 0.54 ml was cooled with ice. And stirred at room temperature for 3 hours. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.15 g of [2- (4-phenoxyphenyl) ethyl] (benzothiazol-6-yl) ether (hereinafter referred to as the present compound 48).
Compound 48

¹ H-NMR (CDCl ₃ ) δ: 3.12 (2H, t, J = 6.9 Hz), 4.23 (2H, t, J = 6.9 Hz), 6.95-7.02 (4H, m), 7.07-7.13 (2H, m ), 7.25-7.27 (2H, m), 7.30-7.35 (2H, m), 7.38 (1H, d, J = 2.4 Hz), 7.97-8.01 (1H, m), 8.80 (1H, s).

¹H-NMR (CDCl₃) δ: 3.12 (2H, t, J = 7.0 Hz), 3.80 (3H, s), 4.25 (2H, t, J = 7.0 Hz), 6.88 (2H, dd, J = 6.6, 2.1 Hz), 7.05 (1H, d, J = 2.9 Hz), 7.23-7.26 (2H, m), 7.34-7.37 (2H, m), 7.99-8.01 (2H, m), 8.75 (1H, dd, J = 4.2, 1.6 Hz). Production Example 49
To a mixed solution of 0.27 g of 4- [2- (quinolin-6-yloxy) ethyl] phenol, 0.16 g of methyl iodide and 3 ml of DMF, 0.39 g of cesium carbonate was added and stirred overnight at room temperature. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed successively with 15% aqueous sodium hydroxide solution, water and hexane, dried and [2- (4-methoxyphenyl) ethyl] (quinolin-6-yl). ) 0.20 g of ether (hereinafter referred to as the present compound 49) was obtained.
Compound 49

¹ H-NMR (CDCl ₃ ) δ: 3.12 (2H, t, J = 7.0 Hz), 3.80 (3H, s), 4.25 (2H, t, J = 7.0 Hz), 6.88 (2H, dd, J = 6.6 , 2.1 Hz), 7.05 (1H, d, J = 2.9 Hz), 7.23-7.26 (2H, m), 7.34-7.37 (2H, m), 7.99-8.01 (2H, m), 8.75 (1H, dd, J = 4.2, 1.6 Hz).

¹H-NMR (CDCl₃) δ: 2.17-2.19 (2H, m), 2.85 (2H, t, J = 7.6 Hz), 4.09 (2H, t, J = 6.3 Hz), 6.94-7.10 (6H, m), 7.19 (2H, dd, J = 6.6, 2.1 Hz), 7.30-7.41 (4H, m), 8.00-8.03 (2H, m), 8.76 (1H, dd, J = 4.3, 1.7 Hz). Production Example 50
To a mixed solution of [3- (3-phenoxyphenyl)] propanol 0.23 g, methanesulfonyl chloride 0.1 ml, and THF 5 ml, 0.20 ml of triethylamine was added dropwise under ice-cooling, and the mixture was stirred for 3 minutes. The reaction mixture was concentrated under reduced pressure to obtain [3- (3-phenoxyphenyl)] propanol methanesulfonate.
A mixture of [3- (3-phenoxyphenyl)] propanolmethanesulfonate, 0.15 g of quinolin-6-ol, 0.40 g of cesium carbonate and 5 ml of DMF obtained by the above operation was stirred overnight at room temperature. Water was added to the reaction mixture under ice cooling, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, so as to obtain 0.40 g of [3- (3-phenoxyphenyl) propyl] (quinolin-6-yl) ether (hereinafter referred to as the present compound 50).
Compound 50

¹ H-NMR (CDCl ₃ ) δ: 2.17-2.19 (2H, m), 2.85 (2H, t, J = 7.6 Hz), 4.09 (2H, t, J = 6.3 Hz), 6.94-7.10 (6H, m ), 7.19 (2H, dd, J = 6.6, 2.1 Hz), 7.30-7.41 (4H, m), 8.00-8.03 (2H, m), 8.76 (1H, dd, J = 4.3, 1.7 Hz).

¹H-NMR (CDCl₃) δ: 3.15 (2H, t, J = 6.9 Hz), 4.29 (2H, t, J = 7.0 Hz), 6.94 (2H, d, J = 8.5 Hz), 6.97-7.05 (4H, m), 7.07 (1H, d, J = 2.9 Hz), 7.28 (2H, d, J = 8.7 Hz), 7.35-7.40 (2H, m), 8.01-8.05 (2H, m), 8.78 (1H, dd, J = 4.2, 1.3 Hz). Production Example 51
3- [2- (Quinolin-6-yloxy) ethyl] phenol 0.30 g, 4-fluorophenylboronic acid 0.31 g, copper (II) acetate 0.21 g, triethylamine 0.79 ml, dried molecular sieve 4A 0.30 g And 5 ml of methylene chloride was stirred at room temperature for 24 hours. Ethyl acetate was added to the reaction mixture, followed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.12 g of {2- [3- (4-fluorophenoxy) phenyl] ethyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 51) 0.11 g. Got.
Compound 51

¹ H-NMR (CDCl ₃ ) δ: 3.15 (2H, t, J = 6.9 Hz), 4.29 (2H, t, J = 7.0 Hz), 6.94 (2H, d, J = 8.5 Hz), 6.97-7.05 ( 4H, m), 7.07 (1H, d, J = 2.9 Hz), 7.28 (2H, d, J = 8.7 Hz), 7.35-7.40 (2H, m), 8.01-8.05 (2H, m), 8.78 (1H , dd, J = 4.2, 1.3 Hz).

¹H-NMR (CDCl₃) δ: 3.18 (2H, t, J = 6.9 Hz), 4.31 (2H, t, J = 7.0 Hz), 6.57-6.81 (4H, m), 7.01 (2H, d, J = 8.5 Hz), 7.09 (1H, d, J = 2.9 Hz), 7.32 (2H, d, J = 8.2 Hz), 7.36-7.41 (2H, m), 8.02 (1H, d, J = 9.2 Hz), 8.04-8.07 (1H, m), 8.77 (1H, dd, J = 4.1, 1.4 Hz). Production Example 52
0.30 g of 3- [2- (quinolin-6-yloxy) ethyl] phenol, 0.31 g of 3-fluorophenylboronic acid, 0.21 g of copper (II) acetate, 1.6 ml of triethylamine, 0.30 g of dried molecular sieves 0.30 g And 5 ml of methylene chloride was stirred at room temperature for 3 days. Water and ethyl acetate were added to the reaction mixture, followed by filtration, and the filtrate was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 0.02-96 g of {2- [3- (3-fluorophenoxy) phenyl] ethyl} (quinolin-6-yl) ether (hereinafter referred to as the present compound 52). Got.
Compound 52

¹ H-NMR (CDCl ₃ ) δ: 3.18 (2H, t, J = 6.9 Hz), 4.31 (2H, t, J = 7.0 Hz), 6.57-6.81 (4H, m), 7.01 (2H, d, J = 8.5 Hz), 7.09 (1H, d, J = 2.9 Hz), 7.32 (2H, d, J = 8.2 Hz), 7.36-7.41 (2H, m), 8.02 (1H, d, J = 9.2 Hz), 8.04-8.07 (1H, m), 8.77 (1H, dd, J = 4.1, 1.4 Hz).

¹H-NMR (DMSO-d₆) δ： 5.52 (2H, s), 7.08 (7H, m), 7.31 (3H, m), 7.55 (1H, dd, J = 8.6, 4.2 Hz), 8.12 (1H, d, J = 9.2 Hz), 8.23 (1H, d, J = 8.9 Hz), 8.79 (1H, dd, J = 4.1, 1.7 Hz). Production Example 53
0.07 g of 55% sodium hydride (oil) was added to a mixture of 0.16 g of 1,5-naphthyridin-2 (1H) -one and 3 ml of DMF under ice cooling, and the mixture was stirred for 30 minutes under ice cooling. To the reaction mixture, 0.42 g of 3-phenoxybenzyl chloride was added under ice cooling, and the mixture was stirred for 20 minutes under ice cooling. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.04 g of [(3-phenoxyphenyl) methyl] (1,5-naphthyridin-2-yl) ether (hereinafter referred to as the present compound 53). .
Compound 53

¹ H-NMR (DMSO-d ₆ ) δ: 5.52 (2H, s), 7.08 (7H, m), 7.31 (3H, m), 7.55 (1H, dd, J = 8.6, 4.2 Hz), 8.12 (1H , d, J = 9.2 Hz), 8.23 (1H, d, J = 8.9 Hz), 8.79 (1H, dd, J = 4.1, 1.7 Hz).

本化合物５５

The compound 54 and the compound 55 can be produced according to the method described in Production Example 1.
Compound 54

Compound 55

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

¹H-NMR (CDCl₃) δ: 3.49 (3H, s), 5.17 (2H, s), 5.20 (2H, s), 7.03 (1H, dd, J = 8.2, 1.7 Hz), 7.12-7.18 (3H, m), 7.31-7.37 (2H, m), 7.44-7.48 (1H, m), 8.01-8.06 (2H, m), 8.78 (1H, dd, J = 4.3, 1.7 Hz). Reference production example 1
To a mixed solution of 10.1 g of quinolin-6-ol, 11.7 g of (3-methoxymethoxy) benzyl alcohol, 22.0 g of triphenylphosphine and 200 ml of THF, 38.0 ml of DEAD (40% toluene solution) was added dropwise under ice cooling. And stirred for 1 hour. After further stirring at room temperature for 2 hours, water was added to the reaction mixture which was concentrated under reduced pressure until the total volume was reduced to about half, and extracted with ethyl acetate. The obtained organic layer was washed successively with aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 12.0 g of {[3- (3-methoxymethoxy) phenyl] methyl} (quinolin-6-yl) ether.
{[3- (3-Methoxymethoxy) phenyl] methyl} (quinolin-6-yl) ether

¹ H-NMR (CDCl ₃ ) δ: 3.49 (3H, s), 5.17 (2H, s), 5.20 (2H, s), 7.03 (1H, dd, J = 8.2, 1.7 Hz), 7.12-7.18 (3H , m), 7.31-7.37 (2H, m), 7.44-7.48 (1H, m), 8.01-8.06 (2H, m), 8.78 (1H, dd, J = 4.3, 1.7 Hz).

¹H-NMR (DMSO-D₆) δ: 5.15 (2H, s), 6.72 (1H, d, J = 7.7 Hz), 6.87-6.91 (2H, m), 7.18 (1H, t, J = 7.6 Hz), 7.43-7.48 (3H, m), 7.92 (1H, d, J = 8.9 Hz), 8.22 (1H, d, J = 8.5 Hz), 8.72-8.74 (1H, m), 9.60 (1H, br s). Reference production example 2
To a mixed solution of 12.0 g of {[3- (3-methoxymethoxy) phenyl] methyl} (quinolin-6-yl) ether and 100 ml of ethanol was added 10 ml of concentrated hydrochloric acid, and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to the concentrated reaction mixture, and the precipitated solid was collected by filtration, washed successively with water and hexane, dried and crude 3- (quinolin-6-yloxymethyl) phenol 3- (quinoline- 7.0 g of 6-yloxymethyl) phenol was obtained.
Crude 3- (quinolin-6-yloxymethyl) phenol

¹ H-NMR (DMSO-D ₆ ) δ: 5.15 (2H, s), 6.72 (1H, d, J = 7.7 Hz), 6.87-6.91 (2H, m), 7.18 (1H, t, J = 7.6 Hz ), 7.43-7.48 (3H, m), 7.92 (1H, d, J = 8.9 Hz), 8.22 (1H, d, J = 8.5 Hz), 8.72-8.74 (1H, m), 9.60 (1H, br s ).

¹H-NMR (CDCl₃) δ: 3.12 (2H, t, J = 7.0 Hz), 3.48 (3H, s), 4.26 (2H, t, J = 7.1 Hz), 5.17 (2H, s), 7.00-7.06 (3H, m), 7.24 (2H, d, J = 8.5 Hz), 7.32-7.39 (2H, m), 7.98-8.03 (2H, m), 8.75 (1H, dd, J = 4.2, 1.6 Hz). Reference production example 3
To a mixed solution of 10.1 g of quinolin-6-ol, 12.7 g of 2- (4-methoxymethoxyphenyl) ethanol, 22.0 g of triphenylphosphine and 200 ml of THF, 38.0 ml of DEAD (40% toluene solution) was cooled with ice. Was added dropwise and stirred for 1 hour. After further stirring at room temperature for 2 hours, water was added to the reaction mixture which was concentrated under reduced pressure until the total volume was reduced to about half, and extracted with ethyl acetate. The obtained organic layer was washed successively with aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 16.9 g of [2- (4-methoxymethoxyphenyl) ethyl] (quinolin-6-yl) ether.
[2- (4-Methoxymethoxyphenyl) ethyl] (quinolin-6-yl) ether

¹ H-NMR (CDCl ₃ ) δ: 3.12 (2H, t, J = 7.0 Hz), 3.48 (3H, s), 4.26 (2H, t, J = 7.1 Hz), 5.17 (2H, s), 7.00- 7.06 (3H, m), 7.24 (2H, d, J = 8.5 Hz), 7.32-7.39 (2H, m), 7.98-8.03 (2H, m), 8.75 (1H, dd, J = 4.2, 1.6 Hz) .

¹H-NMR (DMSO-D₆) δ: 3.02 (2H, t, J = 7.0 Hz), 4.30 (2H, t, J = 7.0 Hz), 6.73 (2H, d, J = 8.2 Hz), 7.16 (2H, d, J = 8.5 Hz), 7.61-7.65 (2H, m), 7.81 (1H, dd, J = 8.5, 4.8 Hz), 8.16 (1H, d, J = 8.9 Hz), 8.70 (1H, d, J = 8.2 Hz), 8.95-8.99 (1H, m), 9.29 (1H, br s). Reference production example 4
To a mixed solution of 10.0 g of [2- (4-methoxymethoxyphenyl) ethyl] (quinolin-6-yl) ether and 100 ml of ethanol was added 10 ml of concentrated hydrochloric acid, and the mixture was stirred overnight at room temperature. Further, 10 ml of concentrated hydrochloric acid was added and stirred at 50 ° C. for 3 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the concentrated reaction mixture, and the precipitated solid was collected by filtration, washed successively with water and hexane, dried, and 7.0 g of 4- [2- (quinolin-6-yloxy) ethyl] phenol. Got.
4- [2- (Quinolin-6-yloxy) ethyl] phenol

¹ H-NMR (DMSO-D ₆ ) δ: 3.02 (2H, t, J = 7.0 Hz), 4.30 (2H, t, J = 7.0 Hz), 6.73 (2H, d, J = 8.2 Hz), 7.16 ( 2H, d, J = 8.5 Hz), 7.61-7.65 (2H, m), 7.81 (1H, dd, J = 8.5, 4.8 Hz), 8.16 (1H, d, J = 8.9 Hz), 8.70 (1H, d , J = 8.2 Hz), 8.95-8.99 (1H, m), 9.29 (1H, br s).

¹H-NMR (CDCl₃) δ: 1.33 (3H, t, J = 7.1 Hz), 4.25 (2H, q, J = 7.2 Hz), 6.38 (1H, d, J = 15.9 Hz), 6.99-7.04 (3H, m), 7.12-7.16 (2H, m), 7.25-7.29 (1H, m), 7.32-7.39 (3H, m), 7.62 (1H, d, J = 15.9 Hz).
３−（３−フェノキシフェニル）アクリル酸エチルエステル６．３ｇ、１０％パラジウム炭素０．３ｇ及びエタノール１００ｍｌの混合物を水素雰囲気下攪拌した。水素ガスの吸収が停止した後、反応混合物をセライト（登録商標）濾過し、濾液を減圧下で濃縮した。
得られた残渣と２０％水酸化ナトリウム水溶液９．３ｇ及びエタノールを還流下で３時間攪拌した。室温まで放冷した反応混合物に水を加え、減圧下濃縮した。次いで該濃縮物に５％塩酸を加えてｐＨを２付近に調節した後に濾過した。得られた固体を水で洗浄後、減圧下乾燥して３−（３−フェノキシフェニル）プロピオン酸４．３ｇを得た。
３−（３−フェノキシフェニル）プロピオン酸

¹H-NMR (DMSO-D₆) δ: 2.51-2.55 (2H, m), 2.81 (2H, t, J = 7.5 Hz), 6.80 (1H, dd, J = 7.7, 2.2 Hz), 6.91 (1H, t, J = 1.9 Hz), 6.97-7.02 (3H, m), 7.13 (1H, td, J = 7.4, 2.7 Hz), 7.29 (1H, t, J = 7.8 Hz), 7.36-7.41 (2H, m).
３−（３−フェノキシフェニル）プロピオン酸１．３ｇとＴＨＦ２０ｍｌとの混合物に、氷冷下でボラン（１Ｍ、ＴＨＦ溶液）を８ｍｌ加えた。氷冷下で1時間攪拌後、反応混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和炭酸水素ナトリウム水溶液及び飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾燥し、減圧下濃縮して［３−（３−フェノキシフェニル）］プロパノール１．２ｇを得た。
［３−（３−フェノキシフェニル）］プロパノール

¹H-NMR (CDCl₃) δ: 1.86-1.90 (2H, m), 2.68-2.70 (2H, m), 3.67 (2H, q, J = 6.0 Hz), 6.82-7.35 (10H, m). Reference production example 5
Under a nitrogen atmosphere, 1.3 g of sodium hydride (55% oil dispersion) and 100 ml of THF were mixed, and 6.8 g of ethyl ethyl diethylphosphonoacetate was added under ice cooling, followed by stirring for 30 minutes under ice cooling. To the mixture, 5.0 g of 3-phenoxybenzyl alcohol was added and stirred at room temperature for 1 hour. To the reaction mixture was added 5% hydrochloric acid, concentrated under reduced pressure, and extracted with ethyl acetate. The obtained organic layer was washed successively with 5% hydrochloric acid, 3% aqueous sodium hydroxide solution, saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 3- (3-phenoxyphenyl). ) 7.3 g of acrylic acid ethyl ester was obtained.
3- (3-Phenoxyphenyl) acrylic acid ethyl ester

¹ H-NMR (CDCl ₃ ) δ: 1.33 (3H, t, J = 7.1 Hz), 4.25 (2H, q, J = 7.2 Hz), 6.38 (1H, d, J = 15.9 Hz), 6.99-7.04 ( 3H, m), 7.12-7.16 (2H, m), 7.25-7.29 (1H, m), 7.32-7.39 (3H, m), 7.62 (1H, d, J = 15.9 Hz).
A mixture of 6.3 g of 3- (3-phenoxyphenyl) acrylic acid ethyl ester, 0.3 g of 10% palladium carbon and 100 ml of ethanol was stirred in a hydrogen atmosphere. After absorption of hydrogen gas stopped, the reaction mixture was filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure.
The obtained residue, 9.3 g of 20% aqueous sodium hydroxide solution and ethanol were stirred under reflux for 3 hours. Water was added to the reaction mixture allowed to cool to room temperature, and the mixture was concentrated under reduced pressure. Next, 5% hydrochloric acid was added to the concentrate to adjust the pH to around 2 and then filtered. The obtained solid was washed with water and then dried under reduced pressure to obtain 4.3 g of 3- (3-phenoxyphenyl) propionic acid.
3- (3-phenoxyphenyl) propionic acid

¹ H-NMR (DMSO-D ₆ ) δ: 2.51-2.55 (2H, m), 2.81 (2H, t, J = 7.5 Hz), 6.80 (1H, dd, J = 7.7, 2.2 Hz), 6.91 (1H , t, J = 1.9 Hz), 6.97-7.02 (3H, m), 7.13 (1H, td, J = 7.4, 2.7 Hz), 7.29 (1H, t, J = 7.8 Hz), 7.36-7.41 (2H, m).
To a mixture of 1.3 g of 3- (3-phenoxyphenyl) propionic acid and 20 ml of THF, 8 ml of borane (1M, THF solution) was added under ice cooling. After stirring for 1 hour under ice cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained 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 to obtain 1.2 g of [3- (3-phenoxyphenyl)] propanol.
[3- (3-phenoxyphenyl)] propanol

¹ H-NMR (CDCl ₃ ) δ: 1.86-1.90 (2H, m), 2.68-2.70 (2H, m), 3.67 (2H, q, J = 6.0 Hz), 6.82-7.35 (10H, m).

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

Formulation Example 1
50 parts of each of the present compounds 1 to 55, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide are thoroughly ground and mixed to obtain each wettable powder.

Formulation Example 2
20 parts of each of the present compounds 1 to 55 and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and finely pulverized by a wet pulverization method. 40 parts of an aqueous solution containing 0.05 part and 0.1 part of aluminum magnesium silicate are added, and further 10 parts of propylene glycol are added and stirred and mixed to obtain each flowable preparation.

Formulation Example 3
2 parts of each of the present compounds 1 to 55, 88 parts of kaolin clay and 10 parts of talc are thoroughly pulverized and mixed to obtain each powder.

Formulation Example 4
Each emulsion is obtained by thoroughly mixing 5 parts of each of the present compounds 1 to 55, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.

Formulation Example 5
2 parts of each of the present compounds 1 to 55, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly pulverized and mixed, and then well kneaded and granulated and dried. Thus, each granule is obtained.

Formulation Example 6
10 parts of each of the present compounds 1 to 55; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain each flowable preparation. .

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.

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. Then, after making this compound 13-16, 25, 31, 33 and 34 into a flowable formulation according to Formulation Example 6, it is diluted with water to a predetermined concentration (500 ppm) so that it sufficiently adheres to the leaf surface of the cucumber. The foliage was sprayed. 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 which processed this compound 13-16, 25, 31, 33 and 34 was 30% or less of the lesion area in an 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 1, 3, 6, 8, 13-16, 18, 20, 28, 40 and 52 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 so as to adhere well to the leaf surface. 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 treated with the present compounds 1, 3, 6, 8, 13-16, 18, 20, 28, 40 and 52 was 30% or less of the lesion area in the untreated plant. It was.

Test example 3
Cucumber gray mold prevention effect test (Botrytis cinerea)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The present compounds 32, 40, 41 and 52 were made into flowable formulations 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 leaves. After spraying, the plants were air-dried, and a PDA medium containing spores of cucumber gray mold was placed on the cucumber leaf surface. After inoculation for 4 days at 12 ° C. and high humidity, the lesion area was examined. As a result, the lesion area on the plant treated with the present compounds 32, 40, 41 and 52 was 30% or less of the lesion area on the untreated plant.

Test example 4
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 present compounds 1, 3, 6-8, 11, 13-22, 24-28, 30-33, 40, 41, 54 and 55 were made into flowable preparations according to Preparation Example 6 and then diluted with water to a predetermined concentration. (500 ppm) and sprayed on the foliage so that it adheres 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 which processed 1, 3, 6-8, 11, 13-22, 24-28, 30-33, 40, 41, 54 and 55 is the lesion area in an untreated plant. 30% or less.

Test Example 5
Radish black spot disease prevention effect test (Alternaria brassicicola)
A plastic pot was filled with sand loam, seeded with Japanese radish (variety; early 40 days), and grown in a greenhouse for 5 days. The compounds 1, 6, 29 and 55 were made into flowable formulations 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 radish leaves. After spraying, the plants were air-dried and spray-inoculated with an aqueous suspension of radish black spot fungus spores. After inoculation, it was first placed at 24 ° C. under high humidity for 1 day and then placed in a greenhouse for 3 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 1, 6, 29 and 55 was 30% or less of the lesion area in the untreated plant.

Test Example 6
Rice blast prevention effect test (Magnaporthe grisea)
A plastic pot was filled with soil, rice (cultivar; Nihonbare) was sown and grown in a greenhouse for 12 days. After making this compound 1, 2, 4-22, 25-27, 29, 30, 32-41 and 48-55 into a flowable preparation according to Preparation Example 6, it was diluted with water to a predetermined concentration (500 ppm), The foliage was sprayed so as to adhere well to the leaf surface of rice. After spraying, the plants were air-dried, and a pot having rice blast diseased leaves was left around the sprayed plants. All the rice plants were placed under high humidity only at night, and the lesion area was examined 5 days after the inoculation. As a result, the lesion area in the plant which processed this compound 1, 2, 4-22, 25-27, 29, 30, 32-41 and 48-55 is 30% or less of the lesion area in an untreated plant. Met.

Test Example 7
Tomato plague prevention effect test (Phytophthora infestans)
A plastic pot was filled with sand loam, seeded with tomato (variety: patio), and grown in a greenhouse for 20 days. Each of the present compounds 6 and 28 was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to adhere well to the leaf surface of the tomato seedling. After air-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 plant treated with the present compounds 6 and 28 was 30% or less of the lesion area in the untreated plant.

Test Example 8
Tomato wilt soil treatment test (irrigation)
A plastic pot is filled with tomato wilt (Fusarium oxysporum) -contaminated soil, seeded with tomato (variety: patio), made into a flowable formulation according to Formulation Example 6, and diluted with water. A soil irrigation treatment is carried out with an amount of the water-diluted solution of 10 mg of the present compound. After cultivating in a greenhouse for 1 month, investigate the growth of plants. As a result, the plants cultivated in the soil (treated area) treated with soil irrigation of this compound are compared with the plants cultivated in the same manner as the treated area in soil (untreated area) where this compound is not irrigated with soil. It can be confirmed that the symptoms of tomato wilt are reduced.

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 the compound is made into a flowable formulation according to Formulation Example 6 and then water. Then, 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, the plants cultivated in the soil (treated area) treated with soil irrigation of this compound are compared with the plants cultivated in the same manner as the treated area in soil (untreated area) where this compound is not irrigated with soil. It can be confirmed that the symptoms of potato half body wilt are reduced.

Test Example 10
Rice Dirt Seed Seed Treatment Test This compound is made into a flowable formulation according to Formulation Example 6 and then diluted to 2000 ppm with water, and seed treated with Gibberella fujikuroi contaminated pods by the dipping method. Thereafter, the seedling box filled with soil is sown with the contaminated rice seeds and cultivated in a greenhouse for one month, and then the growth state of the plant is investigated. As a result, plants cultivated with seed treatment of this compound (treated area) have less symptoms of rice idiot disease compared to plants cultivated in the same manner as the treated area without seed treatment (untreated area). It can be confirmed.

Test Example 11
Wheat Standing Disease Seed Treatment Test This compound is made into a flowable formulation according to Formulation Example 6, and then seeded with the above flowable formulation in an amount of 200 g of this compound per 100 kg seed in seeds contaminated with wheat seedling fungus (Gaeumanomyces graminis). Treat the seeds by the smearing method. 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 after seed treatment with this compound (treated area) are less susceptible to wheat wilt than those grown without treatment (treated area). It can be confirmed.

  According to the present invention, it is possible to control or prevent plant diseases caused by plant pathogens (excluding Aspergillus).

Claims (18)

To control plant diseases caused by plant pathogens (excluding Aspergillus),
Formula (1)

[Where,
A is the following A ¹ , A ² or A ³

(Wherein p represents any integer from 0 to 6,
q represents any integer from 0 to 5,
r represents any integer from 0 to 4;
R ¹ represents a halogen atom, a C1-C4 alkyl group or a cyano group,
R ² represents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group or a cyano group,
R ³ represents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group or a cyano group.
However, when p is an integer from 2 to 6, each R ¹ is the same or different, and when q is an integer from 2 to 5, each R ² is the same or different and r is When R is an integer from 2 to 4, each R ³ is the same or different from each other. )
n represents any integer from 1 to 4,
E represents a furyl group, a thienyl group, a pyrrolyl group, a tetrazolyl group, a thiazolyl group, a pyrazolyl group or a phenyl group;
Any group represented by E may be substituted with at least one group selected from the following substituent group a-1 and substituent group a-2;
[Substituent group a-1]
Halogen atom, amino group, hydroxyl group, mercapto group, cyano group, formyl group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group , 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, C6-10 aryl C2-6 alkenyl Group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5- 10-membered heterocyclic oxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio group, C3-8 cyclo Alkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenylamino group, mono-C2 -6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 aryl C1-6 alkylamino Group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N- 2-6 alkenyl-N-C1-6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6 -10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 Alkylamino group, N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, C1-6 alkylcarbonyl group, C6-10 arylcarbonyl group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, C1-6 alkylsulfinyl group, group (wherein the formula ^{-C (= N-R a1)} R a2, R a1 represents a hydroxyl group or C1-6 alkoxy It refers to the group; R ^a2 represents hydrogen or C1-6 alkyl group. ), A C6-10 aryloxy C1-6 alkyl group, a 5-10 membered heterocyclic oxy C1-6 alkyl group and a C1-C3 trialkylsilyl C2-8 alkynyl group;
[Substituent group a-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio Group, C3-8 cycloalkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenyl Amino group, mono-C2-6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 Aryl C1-6 alkylamino group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1-6 alkylamino group, N- C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6 10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkyl An amino group, an N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxyC1-6 alkyl group;
However, each group described in the substituent group a-2 has 1 to 3 substituents selected from the following substituent group b-1;
[Substituent group b-1]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group , C1-6 alkoxy group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-8 alkylthio group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoro One mono-C6-10 arylamino group and one amino group which may have one methoxy group, mono-C1-6 alkylamino group, di-C1-6 alkylamino group, amino group or aminosulfonyl group N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group which may have]
The agricultural composition containing the ether compound represented by these, its salt, or those hydrates.   In formula (1), E is a furyl group substituted with at least one group selected from substituent group a-1 and substituent group a-2, substituent group a-1 and substituent group a-2. A thienyl group substituted with at least one group selected from: a pyrrolyl group substituted with at least one group selected from substituent group a-1 and substituent group a-2; or substituent group a-1. The agricultural composition according to claim 1, which is a phenyl group substituted with at least one group selected from substituent group a-2. In the formula (1), E is a furyl group substituted with at least one group selected from the following substituent group a-3 and substituent group a-4, the following substituent group a-3 and substituent group Thienyl group substituted with at least one group selected from group a-4, pyrrolyl group substituted with at least one group selected from the following a-3 and substituent group a-4, or the following substituents The agricultural composition according to claim 1, which is a phenyl group substituted with at least one group selected from group a-3 and substituent group a-4.
[Substituent group a-3]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered hetero Cyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1- 8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, 5-10 membered heterocyclic ring C1 -6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 alkynylthio group, C3-8 Loalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl C1-6 alkylthio group, C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino Group, mono-C2-6 alkenylamino group, mono-C2-6 alkynylamino group, mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkyl Amino group, mono-C6-10 aryl C1-6 alkylamino group, mono-5-10 membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1 -6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl -N-C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6 -10 aryl C1-6 alkyl-N-C1-6 alkylamino group, N-5-10 membered heterocyclic C1-6 alkyl-N-C1-6 alkylamino group, C1-6 alkylcarbonyl group, C1-6 alkoxy A carbonyl group, a C1-6 alkylsulfonyl group, a group represented by the formula —C (═N—R ^a1 ) R ^a2 (wherein R ^a1 represents a hydroxyl group or a C1-6 alkoxy group; R ^a2 represents A hydrogen atom or a C1-6 alkyl group), a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxy C1-6 alkyl group;
[Substituent group a-4]
C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C6-10 aryl C1 -6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2-8 Alkynylthio group, C3-8 cycloalkylthio group, C6-10 arylthio group, C3-8 cycloalkyl C1-6 alkylthio C6-10 aryl C1-6 alkylthio group, 5-10 membered heterocyclic C1-6 alkylthio group, mono-C1-6 alkylamino group, mono-C2-6 alkenylamino group, mono-C2-6 alkynylamino group, Mono-C3-8 cycloalkylamino group, mono-C6-10 arylamino group, mono-C3-8 cycloalkyl C1-6 alkylamino group, mono-C6-10 aryl C1-6 alkylamino group, mono-5- 10-membered heterocyclic C1-6 alkylamino group, di-C1-6 alkylamino group, N-C2-6 alkenyl-N-C1-6 alkylamino group, N-C2-6 alkynyl-N-C1-6 alkylamino Group, N-C3-8 cycloalkyl-N-C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N C3-8 cycloalkyl C1-6 alkyl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group, N-5-10 membered heterocycle C1-6 An alkyl-N-C1-6 alkylamino group, a C6-10 aryloxy C1-6 alkyl group and a 5-10 membered heterocyclic oxy C1-6 alkyl group;
However, each group described in the substituent group a-4 has 1 to 3 substituents selected from the following substituent group b-2;
[Substituent group b-2]
Hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, 5-10 membered heterocyclic group, C1-6 alkoxy group, C6- 10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoromethoxy group, mono-C1-6 alkylamino group, di-C1 -6 mono-C6-10 arylamino group which may have one alkylamino group, amino group or aminosulfonyl group and N-C6-10 aryl C1-6 which may have one amino group Alkyl-N-C1-6 alkylamino group] In the formula (1), E represents a furyl group which may have one or two substituents selected from the following substituent group e-1 and substituent group e-2, and the following substituent group e-1 And a thienyl group which may have one or two substituents selected from the substituent group e-2, one or two substituents selected from the following substituent group e-1 and substituent group e-2 The agricultural composition according to claim 1, which is a pyrrolyl group which may have or a phenyl group which may have one or two substituents selected from the following substituent group e-1 and substituent group e-2. object.
[[Substituent group e-1]
Halogen atom, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C6-10 aryl group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6 -10 aryl C1-6 alkyl group, C6-10 aryl C2-6 alkenyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C6-10 arylthio group, C6-10 Aryl C1-6 alkylthio group, mono-C6-10 arylamino group, mono-C6-10 aryl C1- Alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group, C6-10 aryloxy C1-6 alkyl group And a 5-10 membered heterocyclic oxy C1-6 alkyl group;
[Substituent group e-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C6-10 aryl group, C3-8 cycloalkyl C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, 5-10 membered hetero Ring C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1 -6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C6-10 arylthio group, C6-10 aryl C1-6 alkylthio group, mono-C6-10 arylamino group, mono-C6-10 aryl C1-6 alkylamino group, N-C6-10 aryl-N-C1-6 alkylamino group, N-C6-10 aryl C1 6 alkyl -N-C1-6 alkylamino group, C6-10 aryloxy C1-6 alkyl group and 5-10 membered heterocyclic oxy C1-6 alkyl group;
However, each group described in the substituent group e-2 has 1 to 3 substituents selected from the following substituent group f;
[Substituent group f]
Halogen atom, hydroxyl group, cyano group, amino group, nitro group, C3-8 cycloalkyl group, C1-6 alkoxy group, C1-6 alkylthio group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1 -6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, mono-C6-10 arylamino group, trifluoromethyl group, trifluoromethoxy group and C1-6 alkyl group] In the formula (1), E represents a furyl group optionally having 1 or 2 substituents selected from the following substituent group g-1 and substituent group g-2, and the following substituent group g- 1 or a thienyl group optionally having 1 or 2 substituents selected from substituent group g-2, 1 or a substituent selected from substituent group g-1 and substituent group g-2 below. 2. A pyrrolyl group which may have two or a phenyl group which may have one or two substituents selected from the following substituent group g-1 and substituent group g-2. Agricultural composition.
[[Substituent group g-1]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl C1-6 alkyl group, phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, Benzofuryl C1-6 alkyl group, benzothienyl C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, phenoxy group, C3-8 cycloalkyl C1-6 alkoxy group, phenyl A C1-6 alkoxy group, a furyl C1-6 alkoxy group, a thienyl C1-6 alkoxy group, a pyridyl C1-6 alkoxy group, a phenoxy C1-6 alkyl group and a pyridyloxy C1-6 alkyl group;
[Substituent group g-2]
C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl C1-6 alkyl group, phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, Benzofuryl C1-6 alkyl group, benzothienyl C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, phenoxy group, C3-8 cycloalkyl C1-6 alkoxy group, phenyl A C1-6 alkoxy group, a furyl C1-6 alkoxy group, a thienyl C1-6 alkoxy group, a pyridyl C1-6 alkoxy group, a phenoxy C1-6 alkyl group and a pyridyloxy C1-6 alkyl group;
However, each group described in the substituent group g-2 has 1 to 3 substituents selected from the following substituent group h;
[Substituent group h]
Halogen atom, hydroxyl group, cyano group, trifluoromethyl group, C1-6 alkyl group, C1-6 alkoxy group and C1-6 alkylthio group]   The agricultural composition according to claim 5, wherein in formula (1), E is a phenyl group which may have one or two substituents selected from substituent group g-1 and substituent group g-2. object. In the formula (1), E is substituted with at least one group selected from the following substituent group i-1 and a furyl group substituted with at least one group selected from the following substituent group i-1. A thienyl group, a pyrrolyl group substituted with at least one group selected from the following substituent group i-1, or a phenyl group substituted with at least one group selected from the following substituent group i-1 The agricultural composition according to claim 1.
[[Substituent group i-1]
A halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C3-8 alkenyloxy group, a C3-8 alkynyloxy group, a C6-10 aryloxy group, a C6-10 aryl C1-6 alkoxy group, (C1-C2 Alkoxy) C2-C5 alkoxy group]   The agricultural composition according to claim 7, wherein in formula (1), E is a phenyl group substituted with at least one group selected from substituent group i-1. In the formula (1), E is substituted with at least one group selected from the following substituent group j-1 and a furyl group substituted with at least one group selected from the following substituent group j-1. A thienyl group, a pyrrolyl group substituted with at least one group selected from the following substituent group j-1, or a phenyl group substituted with at least one group selected from the following substituent group j-1 The agricultural composition according to claim 1.
[[Substituent group j-1]
Halogen atom, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, (C1-C2 alkoxy) C2-C5 alkoxy group] The agricultural composition according to claim 9, wherein in formula (1), E is a phenyl group substituted with at least one group selected from substituent group j-1. In the formula (1), A is agricultural composition of any one of claims 1 to 10 is A ^1. In the formula (1), A is agricultural composition of any one of claims 1 to 10 is A ^3. In the formula (1), A is A ^1, agricultural composition of any one of claims 1 to 10 p is 0. In the formula (1), A is A ^3, agricultural composition of any one of claims 1 to 10 r is 0.   In Formula (1), n is 1 or 2, The agricultural composition of any one of Claims 1-14.   The agricultural composition according to any one of claims 1 to 15, wherein the phytopathogenic fungus is a phytopathogenic filamentous fungus.   A method for controlling or preventing diseases caused by plant pathogens, wherein an effective amount of the agricultural composition according to any one of claims 1 to 15 is applied to useful crops.   The method according to claim 17, wherein the application method is foliage spraying, soil treatment or seed disinfection.