DE102008059357A1 - Agrochemical composition for the control or prophylaxis of plant diseases caused by plant pathogenic microbes - Google Patents

Abstract

Agricultural composition (A) for controlling plant disease caused by phytopathogenic microbes, with exception of Aspergilluscomprises a cyclic compounds (I) or their salts or hydrates. Agricultural composition for controlling plant disease caused by phytopathogenic microbes, with exception of Aspergilluscomprises a cyclic compound of formula (I) or their salts or hydrates. A : 6-quinoleyl, benzothiazol-6-yl or [1.5]naphthalidine-2-yl (all optionally carrying 1-3 substituents of a1 and a2); X : -NH-C(=Y 1>)-CH 2- or -C(=Y 1>)-NH-CH 2-; Y 1> : O, S or NR1y; R1y : 1-6C alkoxy or CN; E : furyl, thienyl, pyrrolyl, tetrazolyl, thiazolyl, pyrazolyl, or phenyl (all optionally carrying 1 or 2 substitutents of a1 and a2); a1 : halo, OH, mercapto, CN, carboxyl, 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 3-8C cycloalkyl, 6-10C aryl, 5-10 membered heterocyclic , 3-8C cycloalkyl-1-6C alkyl, 3-8C cycloalkylidene-1-6C alkyl, 6-10C aryl-1-6C alkyl, 5-10 membered heterocyclic-1-6C alkyl, 1-6C alkoxy, 2-6C alkenyloxy, 2-6C alkynyloxy, 3-8C cycloalkoxy, 6-10C aryloxy, 3-8C cycloalkyl-1-6C alkoxy, 6-10C aryl-1-6C alkoxy,5-10 membered heterocyclic-1-6C alkoxy, 1-6C alkylthio, 2-6C alkenylthio, 2-6C alkynylthio, 3-8C cycloalkylthio, 6-10C arylthio, 3-8C cycloalkyl-1-6C alkylthio, 6-10C aryl-1-6C alkylthio, 5-10 membered heterocyclic-1-6C alkylthio, 1-6C monoalkylamino, 2-6C monoalkenylamino, 2-6C monoalkynylamino, 3-8C monocycloalkylamino, 6-10C monoarylamino, 3-8C cycloalkyl-1-6C monoalkylamino, 6-10C aryl-1-6C monoalkylamino, 5-10 membered hetericyclic-1-6C monoalkylamino, 1-6C dialkylamino, 2-6C N-alkenyl-1-6C-N-alkylamino, 2-6C N-alkynyl-1-6C-N-alkylamino, 3-8C cycloalkyl-1-6C-N-alkylamino, 6-10C N-aryl-1-6C-N-alkylamino, 3-8C N-cycloalkyl-1-6C alkyl-1-6C-N-alkylamino, 6-10C N-aryl-1-6C alkyl-1-6C-N-alkylamino, 5-10 membered hetericyclic-1-6C alkyl-1-6C-N-alkylamino, 1-6C alkylcarbonyl, 1-6C alkoxycarbonyl, 1-6C alkylsulfonyl, 6-10C aryloxy-1-6C alkyl, 5-10 membered heterocylic-1-6C oxyalkyl or -C(=N-Rx1)Rx2; Rx1 : OH or 1-6C alkoxy; Rx1 : H or 1-6C alkyl; a2 : 1-6C alkyl, 2-6C alkenyl, 2-6C alkynyl, 3-8C cycloalkyl, 6-10C aryl, 5-10 membered heterocyclic , 3-8C cycloalkyl-1-6C alkyl, 6-10C aryl-1-6C alkyl, 5-10 membered heterocyclic-1-6C alkyl, 1-6C alkoxy, 2-6C alkenyloxy, 2-6C alkynyloxy, 3-8C cycloalkoxy, 6-10C aryloxy, 3-8C cycloalkyl-1-6C alkoxy, 6-10C aryl-1-6C alkoxy, 5-10 membered heterocyclic-1-6C alkoxy, 1-6C alkylthio, 2-6C alkenylthio, 2-6C alkynylthio, 3-8C cycloalkylthio, 6-10C arylthio, 3-8C cycloalkyl-1-6C alkylthio, 6-10C aryl-1-6C alkylthio, 5-10 membered heterocyclic-1-6C alkylthio, 1-6C monoalkylamino, 2-6C monoalkenylamino, 2-6C monoalkynylamino, 3-8C monocycloalkylamino, 6-10C monoarylamino, 3-8C cycloalkyl-1-6C monoalkylamino, 6-10C aryl-1-6C monoalkylamino, 5-10 membered hetericyclic-1-6C monoalkylamino, 1-6C dialkylamino, 2-6C N-alkenyl-1-6C-N-alkylamino, 2-6C N-alkynyl-1-6C-N-alkylamino, 3-8C N-cycloalkyl-1-6C-N-alkylamino, 6-10C N-aryl-1-6C-N-alkylamino, 3-8C N-cycloalkyl-1-6C alkyl-1-6C-N-alkylamino, 6-10C N-aryl-1-6C alkyl-1-6C-N-alkylamino, 5-10 membered hetericyclic-1-6C alkyl-1-6C-N-alkylamino, 6-10C aryloxy-1-6C alkyl or 5-10 membered heterocylic-1-6C oxyalkyl (where all groups in substituents a2 carrying 1-3 substituents of b1); and b1 : halo, OH, mercapto, CN, carboxyl, amino, carbamoyl, NO 2, 1-6C alkyl, 3-8C cycloalkyl, 6-10C aryl, 5-10 membered heterocyclic, 1-6C alkoxy, 6-10C aryloxy, 5-10 membered heterocyclyloxy, 1-6C alkoxycarbonyl, 1-6C alkylsulfonyl, trifluoromethyl, trifluoromethoxy, 1-6C monoalkylamino, 1-6C dialkylamino, 1-6C monoarylamino comprising amino or aminosulfonyl, or 6-10C N-aryl-1-6C alkyl-1-6C-N-alkylamino comprising amino. An independent claim is included for process for controlling or preventing plant diseases caused by pytopathogenic microbes, with the exception of Aspergillus, comprising applying (A) to useful cultures. [Image] ACTIVITY : Fungicide. MECHANISM OF ACTION : None given.

Description

The The present invention relates to an agrochemical composition for the control or prevention of plant diseases, which are caused by plant pathogenic microbes, comprising an amide compound, a salt thereof or a hydrate thereof, and a method of controlling or prevention of plant diseases caused by phytopathogenic Microbes are effected, comprising applying an effective amount the above agrochemical composition to be useful Crops.

A Compound of formula (I), as shown below, is known and the production method thereof is also known (cf. Patent Document 1, for example). However, the ability is This compound completely phytopathogenic microbes except to fight or prevent Aspergillus unknown.

wobei A eine 6-Chinolylgruppe, eine Benzothiazol-6-ylgruppe oder eine [1.5]Naphthyridin-2-ylgruppe dargestellt; X einen Rest der Formel -NH-C(=Y)-CH₂- oder einen Rest der Formel -C(=Y)-NH-CH₂- darstellt; Y ein Sauerstoffatom, ein Schwefelatom oder NR^Y darstellt, wobei R^Y einen C1-6-Alkoxyrest oder eine Cyanogruppe darstellt; und E eine Furylgruppe, eine Thienylgruppe, eine Pyrrolylgruppe, eine Tetrazolylgruppe, eine Thiazolylgruppe, eine Pyrazolylgruppe oder eine Phenylgruppe darstellt; wobei A gegebenenfalls einen bis drei Substituenten aufweisen kann, ausgewählt aus der folgenden Substituentengruppe a-1 und Substituentengruppe a-2, und E gegebenenfalls einen oder zwei Substituenten aufweisen kann, ausgewählt aus der folgenden Substituentengruppe a-1 und Substituentengruppe a-2:
[Substituentengruppe a-1]
Halogenatom, Hydroxylgruppe, Mercaptogruppe, Cyanogruppe, Carboxylgruppe, C1-6-Alkylrest, C2-6-Alkenylrest, C2-6-Alkinylrest, C3-8-Cycloalkylrest, C6-10-Arylrest, 5- bis 10-gliedriger heterocyclischer Rest, C3-8-Cycloalkyl-C1-6-alkylrest, C3-8-Cycloalkyliden-C1-6-alkylrest, C6-10-Aryl-C1-6-alkylrest, C6-10-Aryl-C2-6-alkenylrest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkylrest, C1-6-Alkoxyrest, C2-6-Alkenyloxyrest, C2-6-Alkinyloxyrest, C3-8-Cycloalkoxyrest, C6-10-Aryloxyrest, C-3-8-Cycloalkyl-C1-6-alkoxyrest, C6-10-Aryl-C1-6-alkoxyrest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkoxyrest, C1-6-Alkylthiorest, C2-6-Alkenylthiorest, C2-6-Alkinylthiorest, C3-8-Cycloalkylthiorest, C6-10-Arylthiorest, C3-8-Cycloalkyl-C1-6-alkylthiorest, C6-10-Aryl-C1-6-alkylthiorest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkylthiorest, Mono-C1-6-alkylaminorest, Mono-C2-6-alkenylaminorest, Mono-C2-6-alkinylaminorest, Mono-C3-8-cycloalkylaminorest, Mono-C6-10-arylaminorest, Mono-C3-8-cycloalkyl-C1-6-alkylaminorest, Mono-C6-10-aryl-C1-6-alkylaminorest, Mono-5- bis 10-gliedriger heterocyclischer C1-6-alkylaminorest, Di-C1-6-alkylaminorest, N-C2-6-Alkenyl-N-C1-6-alkylaminorest, N-C2-6-Alkinyl-N-C1-6-alkylaminorest, N-C3-8-Cycloalkyl-N-C1-6-alkylaminorest, N-C6-10-Aryl-N-C1-6-alkylaminorest, N-C3-8-Cycloalkyl-C1-6-alkyl-N-C1-6-alkylaminorest, N-C6-10-Aryl-C1-6-alkyl-N-C1-6-alkylaminorest, N-5- bis 10-gliedriger heterocyclischer C1-6-Alkyl-N-C1-6-alkylaminorest, C1-6-Alkylcarbonylrest, C1-6-Alkoxycarbonylrest, C1-6-Alkylsulfonylrest, ein Rest der Formel -C(=N-R^a1)R^a2 (wobei R^a1 eine Hydroxylgruppe oder einen C1-6-Alkoxyrest darstellt; und R^a2 ein Wasserstoffatom oder einen C1-6-Alkylrest darstellt), C6-10-Aryloxy-C1-6-alkylrest und 5- bis 10-gliedriger heterocyclischer Oxy-C1-6-alkylrest; und
[Substituentengruppe a-2]
C1-6-Alkylrest, C2-6-Alkenylrest, C2-6-Alkinylrest, C3-8-Cycloalkylrest, C6-10-Arylrest, 5- bis 10-gliedriger heterocyclischer Rest, C3-8-Cycloalkyl-C1-6-alkylrest, C6-10-Aryl-C1-6-alkylrest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkylrest, C1-6-Alkoxyrest, C2-6-Alkenyloxyrest, C2-6-Alkinyloxyrest, C3-8-Cycloalkoxyrest, C-6-10-Aryloxyrest, C-3-8-Cycloalkyl-C1-6-alkoxyrest, C6-10-Aryl-C1-6-alkoxyrest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkoxyrest, C1-6-Alkylthiorest, C2-6-Alkenylthiorest, C2-6-Alkinylthiorest, C3-8-Cycloalkylthiorest, C6-10-Arylthiorest, C3-8-Cycloalkyl-C1-6-alkylthiorest, C6-10-Aryl-C1-6-alkylthiorest, 5- bis 10-gliedriger heterocyclischer C1-6- Alkylthiorest, Mono-C1-6-alkylaminorest, Mono-C2-6-alkenylaminorest, Mono-C2-6-alkinylaminorest, Mono-C3-8-cycloalkylaminorest, Mono-C6-10-arylaminorest, Mono-C3-8-cycloalkyl-C1-6-alkylaminorest, Mono-C6-10-aryl-C1-6-alkylaminorest, Mono-5- bis 10-gliedriger heterocyclischer C1-6-alkylaminorest, Di-C1-6-alkylaminorest, N-C2-6-Alkenyl-N-C1-6-alkylaminorest, N-C2-6-Alkinyl-N-C1-6-alkylaminorest, N-C3-8-Cycloalkyl-N-C1-6-alkylaminorest, N-C6-10-Aryl-N-C1-6-alkylaminorest, N-C3-8-Cycloalkyl-C1-6-alkyl-N-C1-6-alkylaminorest, N-C6-10-Aryl-C1-6-alkyl-N-C1-6-alkylaminorest, N-5- bis 10-gliedriger heterocyclischer C1-6-Alkyl-N-C1-6-alkylaminorest, C6-10-Aryloxy-C1-6-alkylrest und 5- bis 10-gliedriger heterocyclischer Oxy-C1-6-alkylrest; wobei jeder Rest, der in der Substituentengruppe a-2 beschrieben ist, einen bis drei Substituenten aufweist, ausgewählt aus der folgenden Substituentengruppe b:
[Substituentengruppe b]
Halogenatom, Hydroxylgruppe, Mercaptogruppe, Cyanogruppe, Carboxylgruppe, Aminogruppe, Carbamoylgruppe, Nitrogruppe, C1-6-Alkylrest, C3-8-Cycloalkylrest, C6-10-Arylrest, 5- bis 10-gliedriger heterocyclischer Rest, C1-6-Alkoxyrest, C6-10-Aryloxyrest, 5- bis 10-gliedriger heterocyclischer Oxyrest, C1-6-Alkoxycarbonylrest, C1-6-Alkylsulfonylrest, Trifluormethylgruppe, Trifluormethoxygruppe, Mono-C1-6-alkylaminorest, Di-C1-6-alkylaminorest, Mono-C6-10-Arylaminorest, der gegebenenfalls eine Aminogruppe oder eine Aminosulfonylgruppe aufweist, und N-C6-10-Aryl-C1-6-alkyl-N-C1-6-alkylaminorest, der gegebenenfalls eine Aminogruppe aufweist.

• [Patentdruckschrift 1] Internationale Patentanmeldung Offenlegungsschrift WO2005/033079

A compound of the following formula (I), a salt thereof or a hydrate thereof: Formula I

wherein A represents a 6-quinolyl group, a benzothiazol-6-yl group or a [1.5] naphthyridin-2-yl group; X is a radical of the formula -NH-C (= Y) -CH ₂ - or a radical of the formula -C (= Y) -NH-CH ₂ -; Y represents an oxygen atom, a sulfur atom or NR ^Y , wherein R ^{Y represents} a C 1-6 alkoxy group or a cyano group; and E represents a furyl group, a thienyl group, a pyrrolyl group, a tetrazolyl group, a thiazolyl group, a pyrazolyl group or a phenyl group; wherein A may optionally have one to three substituents selected from the following substituent group a-1 and substituent group a-2, and E may optionally have one or two substituents selected from the following substituent group a-1 and substituent group a-2:
[Substituent group a-1]
Halogen, hydroxyl, mercapto, cyano, carboxyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 member heterocyclic, C3 -8-cycloalkyl-C1-6-alkyl, C3-8-cycloalkylidene-C1-6-alkyl, C6-10-aryl-C1-6-alkyl, C6-10-aryl-C2-6-alkenyl, 5- to 10-membered heterocyclic C1-6-alkyl radical, C1-6-alkoxy radical, C2-6-alkenyloxy radical, C2-6-alkynyloxy radical, C3-8-cycloalkoxy radical, C6-10-aryloxy radical, C-3-8-cycloalkyl-C1- 6-alkoxy, C6-10-aryl-C1-6-alkoxy, 5-10 membered heterocyclic C1-6-alkoxy, C1-6-alkylthio, C2-6-alkenylthio, C2-6-alkynylthio, C3-8 Cycloalkylthio, C6-10-arylthio, C3-8-cycloalkyl-C1-6-alkylthio, C6-10-aryl-C1-6-alkylthio, 5-10-membered heterocyclic C1-6-alkylthio, mono-C1- 6-alkylamino, mono-C2-6-alkenylamino, mono-C2-6-alkynylamino, mono-C3-8-cycloalkylamino, mono-C6-10-arylamino, mono-C3-8-cycloalkyl-C1-6 -alkylamino, mono-C6-10-aryl-C1-6-alkylamino, mono-5-10-membered heterocyclic C1-6-alkylamino, di-C1-6-alkylamino, N-C2-6-alkenyl-N- C1-6-alkylamino, N-C2-6-alkynyl-N-C1-6-alkylamino, N-C3-8-cycloalkyl-N-C1-6-alkylamino, N-C6-10-aryl-N-C1- 6-alkylamino, N-C3-8-cycloalkyl-C1-6-alkyl-N-C1-6-alkylamino, N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino, N- 5- to 10-membered heterocyclic C1-6-alkyl-N-C1-6-alkylamino, C1-6-alkylcarbonyl, C1-6-alkoxycarbonyl, C1-6-alkylsulfonyl, a radical of the formula -C (= ^NRa1 ) R ^a2 (wherein R ^{a1 represents} a hydroxyl group or a C 1-6 alkoxy group; and R ^{a2 represents} a hydrogen atom or a C 1-6 alkyl group), C 6-10 aryloxy C 1-6 alkyl group and 5-10 membered heterocyclic oxy C 1-6 alkyl group; and
[Substituent group a-2]
C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 membered heterocyclic, C3-8 cycloalkyl, C1-6 alkyl , C 6-10 -aryl-C 1-6 -alkyl, 5- to 10-membered heterocyclic C 1-6 -alkyl, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy, C 3-8 -cycloalkoxy, C 6-10 aryloxy, C 3-8 cycloalkyl C 1-6 alkoxy, C 6-10 aryl C 1-6 alkoxy, 5-10 member heterocyclic C 1-6 alkoxy, C 1-6 Alkylthio, C2-6 alkenylthio, C2-6 alkynylthio, C3-8 cycloalkylthio, C6-10 arylthio, C3-8 cycloalkyl C1-6 alkylthio, C6-10 aryl C1-6 alkylthio , 5- to 10-membered heterocyclic C1-6-alkylthio radical, mono-C1-6-alkylamino radical, mono-C2-6-alkenylamino radical, mono-C2-6-alkynylamino radical, mono-C3-8-cycloalkylamino radical, mono-C6- 10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono-C6-10-aryl-C1-6-alkylamino, mono-5- to 10-membered heterocyclic C1-6-alkylamino, di-C1-6-alkylamino, N-C2-6-alkenyl-N-C1-6-alkylamino, N-C2-6-alkynyl-N-C1-6-alkylamino, N-C3- 8-cycloalkyl-N-C 1-6 -alkylamino, N-C 6-10 -aryl-N-C 1-6 -alkylamino, N-C 3-8 -cycloalkyl-C 1-6 -alkyl-N-C 1-6 -alkylamino, N-C6-10 aryl-C1-6-alkyl-N-C1-6-alkylamino, N-5 to 10-membered heterocyclic C1-6-alkyl-N-C1-6-alkylamino, C6-10-aryloxy -C 1-6 -alkyl and 5- to 10-membered heterocyclic oxy-C 1-6 -alkyl; wherein each group described in the substituent group a-2 has one to three substituents selected from the following substituent group b:
[Substituent group b]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C 1-6 alkyl group, C 3-8 cycloalkyl group, C 6-10 aryl group, 5-10 membered heterocyclic group, C 1-6 alkoxy group, C 6 -10-aryloxy, 5- to 10-membered heterocyclic oxy, C1-6-alkoxycarbonyl, C1-6-alkylsulfonyl, trifluoromethyl, trifluoromethoxy, mono-C1-6-alkylamino, di-C1-6-alkylamino, mono-C6- 10-arylamino radical optionally having an amino group or an aminosulfonyl group, and N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino radical optionally having an amino group.

• [Patent Document 1] International Patent Application Laid-Open Publication WO2005 / 033079

A Object of the present invention is a new use of Compound of formula (I) and the like. To provide.

When The result of extensive investigations, the inventors of the present Application found that the compound of formula (I) excellent Action to combat or prevent plant diseases which are caused by plant pathogenic microbes, wherein they completed the present invention.

• (1) Eine agrochemische Zusammensetzung zur Bekämpfung und Vorbeugung von Pflanzenkrankheiten, die durch pflanzenpathogene Mikroben außer Aspergillus bewirkt werden (nachstehend manchmal als die erfindungsgemäße agrochemische Zusammensetzung bezeichnet), umfassend eine Verbindung der Formel (I), ein Salz davon oder ein Hydrat davon (nachstehend manchmal als die vorliegende Verbindung bezeichnet): Formel (I)
  
  wobei A eine 6-Chinolylgruppe, eine Benzothiazol-6-ylgruppe oder eine [1.5]Naphthyridin-2-ylgruppe darstellt; X einen Rest der Formel -NH-C(=Y)-CH₂- oder einen Rest der Formel -C(=Y)-NH-CH₂- darstellt; Y ein Sauerstoffatom, ein Schwefelatom oder NR^Y darstellt, wobei R^Y einen C1-6-Alkoxyrest oder eine Cyanogruppe darstellt; und E eine Furylgruppe, eine Thienylgruppe, eine Pyrrolylgruppe, eine Tetrazolylgruppe, eine Thiazolylgruppe, eine Pyrazolylgruppe oder eine Phenylgruppe darstellt; wobei A gegebenenfalls einen bis drei Substituenten aufweisen kann, ausgewählt aus der folgenden Substituentengruppe a-1 und Substituentengruppe a-2, und E gegebenenfalls einen oder zwei Substituenten aufweisen kann, ausgewählt aus der folgenden Substituentengruppe a-1 und Substituentengruppe a-2: [Substituentengruppe a-1] Halogenatom, Hydroxylgruppe, Mercaptogruppe, Cyanogruppe, Carboxylgruppe, C1-6-Alkylrest, C2-6-Alkenylrest, C2-6-Alkinylrest, C3-8-Cycloalkylrest, C6-10-Arylrest, 5- bis 10-gliedriger heterocyclischer Rest, C3-8-Cycloalkyl-C1-6-alkylrest, C3-8-Cycloalkyliden-C1-6-alkylrest, C6-10-Aryl-C1-6-alkylrest, C6-10-Aryl-C2-6-alkenylrest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkylrest, C1-6-Alkoxyrest, C2-6-Alkenyloxyrest, C2-6-Alkinyloxyrest, C3-8-Cycloalkoxyrest, C6-10-Aryloxyrest, C-3-8-Cycloalkyl-C1-6-alkoxyrest, C6-10-Aryl-C1-6-alkoxyrest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkoxyrest, C1-6-Alkylthiorest, C2-6-Alkenylthiorest, C2-6-Alkinylthiorest, C3-8-Cycloalkylthiorest, C6-10-Arylthiorest, C3-8-Cycloalkyl-C1-6-alkylthiorest, C6-10-Aryl-C1-6-alkylthiorest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkylthiorest, Mono-C1-6-alkylaminorest, Mono-C2-6-alkenylaminorest, Mono-C2-6-alkinylaminorest, Mono-C3-8-cycloalkylaminorest, Mono-C6-10-arylaminorest, Mono-C3-8-cycloalkyl-C1-6-alkylaminorest, Mono-C6-10-aryl-C1-6-alkylaminorest, Mono-5- bis 10-gliedriger heterocyclischer C1-6-Alkylaminorest, Di-C1-6-alkylaminorest, N-C2-6-Alkenyl-N-C1-6-alkylaminorest, N-C2-6-Alkinyl-N-C1-6-alkylaminorest, N-C3-8-Cycloalkyl-N-C1-6-alkylaminorest, N-C6-10-Aryl-N-C1-6-alkylaminorest, N-C3-8-Cycloalkyl-C1-6-alkyl-N-C1-6-alkylaminorest, N-C6-10-Aryl-C1-6-alkyl-N-C1-6-alkylaminorest, N-5- bis 10-gliedriger heterocyclischer C1-6-Alkyl-N-C1-6-alkylaminorest, C1-6-Alkylcarbonylrest, C1-6-Alkoxycarbonylrest, C1-6-Alkylsulfonylrest, ein Rest der Formel -C(=N-R^a1)R^a2 (wobei R^a1 eine Hydroxylgruppe oder einen C1-6-Alkoxyrest darstellt; und R^a2 ein Wasserstoffatom oder einen C1-6-Alkylrest darstellt), C6-10-Aryloxy-C1-6-alkylrest und 5- bis 10-gliedriger heterocyclischer Oxy-C1-6-alkylrest; und [Substituentengruppe a-2] C1-6-Alkylrest, C2-6-Alkenylrest, C2-6-Alkinylrest, C3-8-Cycloalkylrest, C6-10-Arylrest, 5- bis 10-gliedriger heterocyclischer Rest, C3-8-Cycloalkyl-C1-6-alkylrest, C6-10-Aryl-C1-6-alkylrest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkylrest, C1-6-Alkoxyrest, C2-6-Alkenyloxyrest, C2-6-Alkinyloxyrest, C3-8-Cycloalkoxyrest, C-6-10-Aryloxyrest, C-3-8-Cycloalkyl-C1-6-alkoxyrest, C6-10-Aryl-C1-6-alkoxyrest, 5- bis 10-gliedriger heterocyclischer C1-6-Alkoxyrest, C1-6-Alkylthiorest, C2-6-Alkenylthiorest, C2-6-Alkinylthiorest, C3-8-Cycloalkylthiorest, C6-10-Arylthiorest, C3-8-Cycloalkyl-C1-6-alkylthiorest, C6-10-Aryl-C1-6-alkylthiorest, 5- bis 10-gliedriger heterocyclischer C1-6-alkylthiorest, Mono-C1-6-alkylaminorest, Mono-C2-6-alkenylaminorest, Mono-C2-6-alkinylaminorest, Mono-C3-8-cycloalkylaminorest, Mono-C6-10-arylaminorest, Mono-C3-8-cycloalkyl-C1-6-alkylaminorest, Mono-C6-10-aryl-C1-6-alkylaminorest, Mono-5- bis 10-gliedriger heterocyclischer C1-6-alkylaminorest, Di-C1-6-alkylaminorest, N-C2-6-Alkenyl-N-C1-6-alkylaminorest, N-C2-6-Alkinyl-N-C1-6-alkylaminorest, N-C3-8-Cycloalkyl-N-C1-6-alkylaminorest, N-C6-10-Aryl-N-C1-6-alkylaminorest, N-C3-8-Cycloalkyl-C1-6-alkyl-N-C1-6-alkylaminorest, N-C6-10-Aryl-C1-6-alkyl-N-C1-6-alkylaminorest, N-5- bis 10-gliedriger heterocyclischer C1-6-Alkyl-N-C1-6-alkylaminorest, C6-10-Aryloxy-C1-6-alkylrest und 5- bis 10-gliedriger heterocyclischer Oxy-C1-6-alkylrest; wobei jeder Rest, der in der Substituentengruppe a-2 beschrieben ist, einen bis drei Substituenten aufweist, ausgewählt aus der folgenden Substituentengruppe b: [Substituentengruppe b] Halogenatom, Hydroxylgruppe, Mercaptogruppe, Cyanogruppe, Carboxylgruppe, Aminogruppe, Carbamoylgruppe, Nitrogruppe, C1-6-Alkylrest, C3-8-Cycloalkylrest, C6-10-Arylrest, 5- bis 10-gliedriger heterocyclischer Rest, C1-6-Alkoxyrest, C6-10-Aryloxyrest, 5- bis 10-gliedriger heterocyclischer Oxyrest, C1-6-Alkoxycarbonylrest, C1-6-Alkylsulfonylrest, Trifluormethylgruppe, Trifluormethoxygruppe, Mono-C1-6-alkylaminorest, Di-C1-6-alkylaminorest, Mono-C6-10-Arylaminorest, der gegebenenfalls eine Aminogruppe oder eine Aminosulfonylgruppe aufweist, und N-C6-10-Aryl-C1-6-alkyl-N-C1-6-alkylaminorest, der gegebenenfalls eine Aminogruppe aufweist.
• (2) Ein Verfahren zur Bekämpfung oder Vorbeugung von Pflanzenkrankheiten, die durch pflanzenpathogene Mikroben außer Aspergillus hervorgerufen werden, umfassend Aufbringen einer wirksamen Menge der erfindungsgemäßen agrochemischen Zusammensetzung auf nützliche Feldfrüchte.
• (3) Verwendung der Verbindung der Formel (I), eines Salzes davon oder eines Hydrats davon der vorliegenden Erfindung zur Herstellung einer agrochemischen Zusammensetzung.

More specifically, the present invention provides the following (1) to (3).

• (1) An agrochemical composition for controlling and preventing plant diseases caused by plant pathogenic microbes other than Aspergillus (hereinafter sometimes referred to as the agrochemical composition of the present invention) comprising a compound of the formula (I), a salt thereof or a hydrate thereof (hereinafter sometimes referred to as the present compound): Formula (I)
  
  wherein A represents a 6-quinolyl group, a benzothiazol-6-yl group or a [1.5] naphthyridin-2-yl group; X is a radical of the formula -NH-C (= Y) -CH ₂ - or a radical of the formula -C (= Y) -NH-CH ₂ -; Y represents an oxygen atom, a sulfur atom or NR ^Y , wherein R ^{Y represents} a C 1-6 alkoxy group or a cyano group; and E represents a furyl group, a thienyl group, a pyrrolyl group, a tetrazolyl group, a thiazolyl group, a pyrazolyl group or a phenyl group; wherein A may optionally have one to three substituents selected from the following substituent group a-1 and substituent group a-2, and E may optionally have one or two substituents selected from the following substituent group a-1 and substituent group a-2: [Substituent group a-1] halogen, hydroxyl, mercapto, cyano, carboxyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-8 cycloalkyl, C 6-10 aryl, 5-10-membered heterocyclic group, C 3-8 cycloalkyl-C 1-6 alkyl group, C 3-8 cycloalkylidene C 1-6 alkyl group, C 6-10 aryl C 1-6 alkyl group, C 6-10 aryl C 2-6 alkenyl group , 5- to 10-membered heterocyclic C1-6-alkyl group, C1-6-alkoxy group, C2-6-alkenyloxy group, C2-6-alkynyloxy group, C3-8-cycloalkoxy group, C6-10-aryloxy group, C-3-8- Cycloalkyl-C 1-6 -alkoxy, C 6-10 -aryl-C 1-6 -alkoxy, 5-10-membered C 1-6 -cyclocyclic alkoxy, C 1-6 -alkylthio, C 2-6 alkenylthio, C 2-6 -alkynylthio , C3-8-Cy cloalkylthio, C6-10-arylthio, C3-8 -cycloalkyl-C1-6-alkylthio, C6-10-aryl-C1-6-alkylthio, 5-10-membered heterocyclic C1-6-alkylthio, mono-C1-6 -alkylamino, mono-C2-6-alkenylamino, mono-C2-6-alkynylamino, mono-C3-8-cycloalkylamino, mono-C6-10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono -C6-10-aryl-C1-6-alkylamino, mono-5- to 10-membered heterocyclic C1-6-alkylamino, di-C1-6-alkylamino, N-C2-6-alkenyl-N-C1-6- alkylamino, N-C2-6-alkynyl-N-C1-6-alkylamino, N-C3-8-cycloalkyl-N-C1-6-alkylamino, N-C6-10-aryl-N-C1-6-alkylamino, N-C3-8-cycloalkyl-C1-6-alkyl-N-C1- 6-alkylamino, N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino, N-5 to 10-membered heterocyclic C1-6-alkyl-N-C1-6-alkylamino, C1 -6-alkylcarbonyl, C 1-6 -alkoxycarbonyl, C 1-6 -alkylsulfonyl, a radical of formula -C (= NR ^a1 ) R ^a2 (wherein R ^{a1 represents} a hydroxyl group or a C 1-6 alkoxy radical, and R ^{a2 represents} a hydrogen atom or a C1-6 alkyl group), C6-10 aryloxy C1-6 alkyl group and 5-10 membered heterocyclic oxy C1-6 alkyl group; and [Substituent Group a-2] C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 3-8 -cycloalkyl, C 6-10 -aryl, 5-10-membered heterocyclic, C 3-8 -alkyl Cycloalkyl-C 1-6 -alkyl, C 6-10 -aryl-C 1-6 -alkyl, 5-10-membered C 1-6 -heterocyclic, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy , C 3-8 -cycloalkoxy, C 6-10 -aryloxy, C 3-8 -cycloalkyl-C 1-6 -alkoxy, C 6-10 -aryl-C 1-6 -alkoxy, 5-10-membered heterocyclic C 1-6 6-alkoxy, C1-6-alkylthio, C2-6-alkenylthio, C2-6-alkynylthio, C3-8 -cycloalkylthio, C6-10-arylthio, C3-8-cycloalkyl-C1-6-alkylthio, C6-10- Aryl-C 1-6 -alkylthio, 5- to 10-membered heterocyclic C 1-6 -alkylthio, mono-C 1-6 -alkylamino, mono-C 2-6 -alkenylamino, mono-C 2-6 -alkynylamino, mono C 3-8 -cycloalkylamino, mono-C6-10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono-C6-10-aryl-C1-6-alkylamino, mono-5- to 10-membered heterocyclic C1- 6-alkyla minor, di-C1-6-alkylamino, N-C2-6-alkenyl-N-C1-6-alkylamino, N-C2-6-alkynyl-N-C1-6-alkylamino, N-C3-8-cycloalkyl N-C 1-6 -alkylamino, N-C 6-10 -aryl-N-C 1-6 -alkylamino, N-C 3-8 -cycloalkyl-C 1-6 -alkyl-N-C 1-6 -alkylamino, N-C 6 10-aryl-C 1-6 -alkyl-N-C 1-6 -alkylamino, N-5-10-membered heterocyclic C 1-6 -alkyl-N-C 1-6 -alkylamino, C 6-10 -aryloxy-C 1-6 alkyl and 5- to 10-membered heterocyclic oxy-C1-6-alkyl; wherein each group described in the substituent group a-2 has one to three substituents selected from the following substituent group b: [Substituent group b] halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 Alkyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 member heterocyclic, C1-6 alkoxy, C6-10 aryloxy, 5-10 member heterocyclic oxy, C1-6 alkoxycarbonyl , C1-6-alkylsulfonyl, trifluoromethyl, trifluoromethoxy, mono-C1-6-alkylamino, di-C1-6-alkylamino, mono-C6-10-arylamino, optionally having an amino group or an aminosulfonyl group, and N-C6-10 -Aryl-C1-6-alkyl-N-C1-6-alkylamino radical, which optionally has an amino group.
• (2) A method for controlling or preventing plant diseases caused by plant pathogenic microbes other than Aspergillus, comprising applying an effective amount of the agrochemical composition of the present invention to useful crops.
• (3) Use of the compound of the formula (I), a salt thereof or a hydrate thereof of the present invention for the preparation of an agrochemical composition.

According to the Present invention can provide plant diseases which caused by plant pathogenic microbes except Aspergillus become, be fought or prevented.

A in the formula (I) representing the present compound gives a 6-quinolyl group optionally having one to three substituents selected from the following substituent group a-1 and substituent group a-2, a benzothiazol-6-yl group optionally having one to three substituents selected from the following substituent group a-1 and substituent group a-2, or a [1.5] naphthyridin-2-yl group optionally having one to three substituents selected from the following substituent group a-1 and Substituent group a-2:
[Substituent group a-1]
Halogen, hydroxyl, mercapto, cyano, carboxyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 member heterocyclic, C3 -8-cycloalkyl-C1-6-alkyl, C3-8-cycloalkylidene-C1-6-alkyl, C6-10-aryl-C1-6-alkyl, C6-10-aryl-C2-6-alkenyl, 5- to 10-membered heterocyclic C1-6-alkyl radical, C1-6-alkoxy radical, C2-6-alkenyloxy radical, C2-6-alkynyloxy radical, C3-8-cycloalkoxy radical, C6-10-aryloxy radical, C-3-8-cycloalkyl-C1- 6-alkoxy, C6-10-aryl-C1-6-alkoxy, 5-10 membered heterocyclic C1-6-alkoxy, C1-6-alkylthio, C2-6-alkenylthio, C2-6-alkynylthio, C3-8 Cycloalkylthio, C6-10-arylthio, C3-8-cycloalkyl-C1-6-alkylthio, C6-10-aryl-C1-6-alkylthio, 5-10-membered heterocyclic C1-6-alkylthio, mono-C1- 6-alkylamino, mono-C2-6-alkenylamino, mono-C2-6-alkynylamino, mono-C3-8-cycloalkylamino, mono-C6-10-arylamino, mono-C3 -8-cycloalkyl-C1 -6-alkylamino, mono-C6-10-aryl-C1-6-alkylamino, mono-5- to 10-membered heterocyclic C1-6-alkylamino, di-C1-6-alkylamino, N-C2-6-alkenyl N-C 1-6 -alkylamino, N-C 2-6 -alkynyl-N-C 1-6 -alkylamino, N-C 3-8 -cycloalkyl-N-C 1-6 -alkylamino, N-C 6 -10-aryl-N- C1-6-alkylamino, N-C3-8-cycloalkyl-C1-6-alkyl-N-C1-6-alkylamino, N-C6-10 aryl-C1-6-alkyl-N-C1-6-alkylamino, N-5 to 10-membered heterocyclic C1-6-alkyl-N-C1-6-alkylamino, C1-6-alkylcarbonyl , C1-6-alkoxycarbonyl, C1-6-alkylsulfonyl, a radical of the formula -C (= NR ^a1 ) R ^a2 (wherein R ^{a1 represents} a hydroxyl group or a C 1-6 -alkoxy radical, and R ^{a2 represents} a hydrogen atom or a C1- 6-alkyl), C6-10-aryloxy-C1-6-alkyl and 5-10-membered heterocyclic oxy-C1-6-alkyl; and
[Substituent group a-2]
C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 membered heterocyclic, C3-8 cycloalkyl, C1-6 alkyl , C 6-10 -aryl-C 1-6 -alkyl, 5- to 10-membered heterocyclic C 1-6 -alkyl, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy, C 3-8 -cycloalkoxy, C 6-10 aryloxy, C 3-8 cycloalkyl C 1-6 alkoxy, C 6-10 aryl C 1-6 alkoxy, 5-10 member heterocyclic C 1-6 alkoxy, C 1-6 Alkylthio, C2-6 alkenylthio, C2-6 alkynylthio, C3-8 cycloalkylthio, C6-10 arylthio, C3-8 cycloalkyl C1-6 alkylthio, C6-10 aryl C1-6 alkylthio , 5- to 10-membered heterocyclic C1-6-alkylthio, mono-C1-6-alkylamino, mono-C2-6-alkenylamino, mono-C2-6-alkynylamino, mono-C3-8-cycloalkylamino, mono-C6- 10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono-C6-10-aryl-C1-6-alkylamino, mono-5-10-membered heterocyclic C1-6-alkylamino, Di-C1 -6-alkylaminore st, N-C2-6-alkenyl-N-C1-6-alkylamino, N-C2-6-alkynyl-N-C1-6-alkylamino, N-C3-8-cycloalkyl-N-C1-6-alkylamino, N-C6-10 aryl-N-C1-6-alkylamino, N-C3-8-cycloalkyl-C1-6-alkyl-N-C1-6-alkylamino, N-C6-10-aryl-C1-6- Alkyl-N-C 1-6 -alkylamino, N-5-10-membered heterocyclic C 1-6 -alkyl-N-C 1-6 -alkylamino, C 6-10 aryloxy-C 1-6 -alkyl and 5-10 hetero-cyclic heterocyclic oxy-C1-6-alkyl radical; wherein each group described in the substituent group a-2 has one to three substituents selected from the following substituent group b:
[Substituent group b]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C 1-6 alkyl group, C 3-8 cycloalkyl group, C 6-10 aryl group, 5-10 membered heterocyclic group, C 1-6 alkoxy group, C 6 -10-aryloxy, 5- to 10-membered heterocyclic oxy, C1-6-alkoxycarbonyl, C1-6-alkylsulfonyl, trifluoromethyl, trifluoromethoxy, mono-C1-6-alkylamino, di-C1-6-alkylamino, mono-C6- 10-arylamino radical optionally having an amino group or an aminosulfonyl group, and N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino radical optionally having an amino group.

In addition, examples of such a group A may include a 6-quinolyl group optionally having one to three substituents selected from the following substituent group c-1 and substituent group c-2, a benzothiazol-6-yl group optionally having one to three substituents from the following substituent group c-1 and substituent group c-2, and a [1.5] naphthyridin-2-yl group optionally having one to three substituents selected from the following substituent group c-1 and substituent group c-2:
[Substituent group c-1]
Halogen, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 member heterocyclic, C3-8 cycloalkyl C1-6 alkyl, C6-10 aryl C1-6 alkyl, C6-10 aryl C2-6 alkenyl, 5-10 membered heterocyclic C1-6 alkyl, C1-6 alkoxy, C2-6 Alkenyloxy, C2-6 alkynyloxy, C3-8 cycloalkyl C1-6 alkoxy, C6-10 aryl C1-6 alkoxy, 5-10 membered heterocyclic C1-6 alkoxy, mono C2-6 alkylamino, mono C 3-8 alkenylamino, mono C 6-10 alkynylamino, mono C 3-8 cycloalkylamino, mono C 1-6 arylamino, mono C 6-10 cycloalkyl C 1-6 alkylamino, mono -C 1-6 -aryl-C 1-6 -alkylamino, mono 5- to 10-membered heterocyclic C 1-6 -alkylamino, C 2-6 -alkylcarbonyl and a radical of the formula -C (= N-OH) R a ² (wherein R ^{a2 has} the meanings given above); and
[Substituent group c-2]
C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 membered heterocyclic, C3-8 cycloalkyl, C1-6 alkyl , C 6-10 -aryl-C 1-6 -alkyl, 5- to 10-membered heterocyclic C 1-6 -alkyl, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy, C 3-8 -cycloalkyl C1-6 alkoxy, C6-10 aryl C1-6 alkoxy, 5-10 member heterocyclic C1-6 alkoxy, mono C1-6 alkylamino, mono C2-6 alkenylamino, mono C2 -6-alkynylamino, mono-C3-8-cycloalkylamino, mono-C6-10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono-C6-10-aryl-C1-6-alkylamino and mono -5- to 10-membered heterocyclic C1-6-alkylamino radical (wherein each radical described in the substituent group c-2 has one to three substituents selected from the following substituent group d):
[Substituent group d]
Halogen atom, hydroxyl group, carboxyl group, amino group, carbamoyl group, C 1-6 alkoxy group, mono C 1-6 alkylamino group, di C 1-6 alkylamino group, mono C 6-10 arylamino group which may have an amino group or an aminosulfonyl group, N -C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino radical, which gave optionally having an amino group, cyano group, C6-10 aryl group, 5-10 membered heterocyclic group and C1-6 alkoxycarbonyl group.

Furthermore Examples of such a group A may preferably be one 6-quinolyl group, a benzothiazol-6-yl group and a [1.5] naphthyridin-2-yl group lock in.

X in the formula (I) representing the present compound indicates a group of the formula -NH-C (= Y) -CH ₂ - and a group of the formula -C (= Y) -NH-CH ₂ -. The above-mentioned Y represents an oxygen atom, a sulfur atom or NR ^Y (wherein R ^{Y represents} a C 1-6 alkoxy group or a cyano group). X is preferably a group of the formula -NH-C (= Y) -CH ₂ - and Y is preferably an oxygen atom.

E in the formula (I) which is the above compound gives a furyl group optionally having one or two substituents selected from the following substituent group a-1 and substituent group a-2, a thienyl group optionally having one or two substituents selected from the following substituent group a-1 and substituent group a-2, a pyrrolyl group optionally having one or two substituents selected from the following substituent group a-1 and substituent group a-2, or a phenyl group optionally having one or two Substituents selected from the following substituent group a-1 and substituent group a-2:
[Substituent group a-1]
Halogen, hydroxyl, mercapto, cyano, carboxyl, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 member heterocyclic, C3 -8-cycloalkyl-C1-6-alkyl, C3-8-cycloalkylidene-C1-6-alkyl, C6-10-aryl-C1-6-alkyl, C6-10-aryl-C2-6-alkenyl, 5- to 10-membered heterocyclic C1-6-alkyl radical, C1-6-alkoxy radical, C2-6-alkenyloxy radical, C2-6-alkynyloxy radical, C3-8-cycloalkoxy radical, C6-10-aryloxy radical, C-3-8-cycloalkyl-C1- 6-alkoxy, C6-10-aryl-C1-6-alkoxy, 5-10 membered heterocyclic C1-6-alkoxy, C1-6-alkylthio, C2-6-alkenylthio, C2-6-alkynylthio, C3 -8 Cycloalkylthio, C6-10-arylthio, C3-8-cycloalkyl-C1-6-alkylthio, C6-10-aryl-C1-6-alkylthio, 5-10-membered heterocyclic C1-6-alkylthio, mono-C1- 6-alkylamino, mono-C2-6-alkenylamino, mono-C2-6-alkynylamino, mono-C3-8-cycloalkylamino, mono-C6-10-arylamino, mono-C3-8-cycloalkyl-C1- 6-alkylamino, mono-C6-10-aryl-C1-6-alkylamino, mono-5-10-membered heterocyclic C1-6-alkylamino, di-C1-6-alkylamino, N-C2-6-alkenyl-N -C 1-6 -alkylamino, N-C 2-6 -alkynyl-N-C 1-6 -alkylamino, N-C 3-8 -cycloalkyl-N-C 1-6 -alkylamino, N-C 6-10 -aryl-N-C 1 -6-alkylamino, N-C3-8-cycloalkyl-C1-6-alkyl-N-C1-6-alkylamino, N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino, N -5- to 10-membered heterocyclic C1-6-alkyl-N-C1-6-alkylamino, C1-6-alkylcarbonyl, C1-6-alkoxycarbonyl, C1-6-alkylsulfonyl, a radical of the formula -C (= NR ^a1 R ^a2 (wherein R ^{a1 represents} a hydroxyl group or a C 1-6 alkoxy group; and R ^{a2 represents} a hydrogen atom or a C 1-6 alkyl group), C 6-10 aryloxy C 1-6 alkyl group and 5-10 membered heterocyclic oxy C 1-6 alkyl group; and
[Substituent group a-2]
C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 membered heterocyclic, C3-8 cycloalkyl, C1-6 alkyl , C 6-10 -aryl-C 1-6 -alkyl, 5- to 10-membered heterocyclic C 1-6 -alkyl, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy, C 3-8 -cycloalkoxy, C 6-10 aryloxy, C 3-3 cycloalkyl C 1-6 alkoxy, C 6-10 aryl C 1-6 alkoxy, 5-10 member heterocyclic C 1-6 alkoxy, C 1-6 Alkylthio, C2-6 alkenylthio, C2-6 alkynylthio, C3-8 cycloalkylthio, C6-10 arylthio, C3-8 cycloalkyl C1-6 alkylthio, C6-10 aryl C1-6 alkylthio , 5- to 10-membered heterocyclic C1-6-alkylthio radical, mono-C1-6-alkylamino radical, mono-C2-6-alkenylamino radical, mono-C2-6-alkynylamino radical, mono-C3-8-cycloalkylamino radical, mono-C6- 10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono-C6-10-aryl-C1-6-alkylamino, mono-5- to 10- membered heterocyclic C1-6-alkylamino, di-C1 -6-alkylamino N-C2-6-alkenyl-N-C1-6-alkylamino, N-C2-6-alkynyl-N-C1-6-alkylamino, N-C3-8-cycloalkyl-N-C1-6-alkylamino, N-C6-10 aryl-N-C1-6-alkylamino, N-C3-8-cycloalkyl-C1-6-alkyl-N-C1-6-alkylamino, N-C6-10-aryl-C1-6- Alkyl-N-C 1-6 -alkylamino, N-5-10-membered heterocyclic C 1-6 -alkyl-N-C 1-6 -alkylamino, C 6-10 aryloxy-C 1-6 -alkyl and 5-10 hetero-cyclic heterocyclic oxy-C1-6-alkyl radical; wherein each group described in substituent group a-2 has one to three substituents selected from the following substituent group b:
[Substituent group b]
Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C 1-6 alkyl group, C 3-8 cycloalkyl group, C 6-10 aryl group, 5-10 membered heterocyclic group, C 1-6 alkoxy group, C 6 -10-aryloxy, 5- to 10-membered heterocyclic oxy, C1-6-alkoxycarbonyl, C1-6-alkylsulfonyl, trifluoromethyl, trifluoromethoxy, mono-C1-6-alkylamino, di-C1-6-alkylamino, mono-C6- 10-arylamino radical optionally having an amino group or an aminosulfonyl group, and N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino radical optionally containing an amino group has.

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

More preferably, such radicals may be E radicals in which one or two hydrogen atoms of any of a 2-furyl group, a 2-thienyl group, a pyrrolyl group and a phenyl group are substituted by [a fluorine atom, a chlorine atom, a C 1-6 alkyl radical (optionally substituted with one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a C 2-6 -alkenyl radical (optionally substituted by one to three halogen atoms , C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a C 2-6 -alkynyl radical (optionally substituted by one to three halogen atoms, C 3-5 -alkyl) Cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a phenyl group (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy C3-5-cycloalkyl-C1-6-alkyl radical (optionally substituted by one to three halogen atoms or C1-6-alkyl radicals), a C3-5-cycloalkylidene-C1-6-alkyl radical ( optionally substituted with one to three halogen atoms or C 1-6 alkyl radicals), a phenyl C 1-6 alkyl radical (optionally substituted with one to three halogen atoms, C 3-5 cycloalkyl radicals, C 1-6 alkoxy radicals, phenoxy groups, 5- or 6 heterocyclic or C1-6 alkyl radicals), a phenyl-C 2-6 alkenyl radical (optionally substituted with one to three halogen atoms, C 3-5 cycloalkyl radicals, C 1-6 alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic Oxy radicals or C 1-6 -alkyl radicals), a 5- or 6-membered heterocyclic C 1-6 -alkyl radical (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6- heterocyclic oxo radicals or C1-6-alkyl radicals), a C1-6-alkoxy radical ( optionally substituted with one to three halogen atoms or C 1-6 alkyl radicals), a C 3-6 alkenyloxy radical (optionally substituted with one to three halogen atoms or C 1-6 alkyl radicals), a C 3-6 alkynyloxy radical (optionally substituted with one to three Halogen atoms or C 1-6 -alkyl radicals), a phenoxy group (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a C 3-6 -cycloalkyl-C 1-6 -alkoxy radical optionally substituted by one to three halogen atoms, a phenyl-C 1-6 -alkoxy radical (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, Phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a 5- or 6-membered heterocyclic C 1-6 -alkoxy radical (optionally substituted with one to three halo toms, C3-5 cycloalkyl radicals, C1-6 alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C1-6 alkyl radicals), a C6-10 aryloxy C1-6 alkyl radical (optionally substituted with a bis three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups or 5- or 6-membered heterocyclic oxy radicals) or a 5- or 6-membered heterocyclic oxy-C 1-6 -alkyl radical (optionally substituted by one to three halogen atoms , C3-5-cycloalkyl radicals or C1-6-alkoxy radicals)] may be replaced.

Most preferably, such radicals E may be radicals in which one or two hydrogen atoms of any of a 2-furyl group, a 2-thienyl group and a phenyl group are represented by [a fluorine atom, a chlorine atom, a C 1-6 alkyl radical (optionally substituted with one to three Halogen atoms, C3-5 cycloalkyl radicals, C1-6 alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy groups or C1-6-alkyl radicals), a C2-6 alkenyl radical (optionally substituted by one to three halogen atoms, C3-5 Cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a C 2-6 -alkenyl radical (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1 - 6-alkoxy, phenoxy, 5- or 6-membered heterocyclic oxy or C 1-6 -alkyl), a C 2-6 alkynyl (optionally substituted with one to three halogens, C 3-5 cycloalkyl, C 1-6 alkoxy, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a phenyl group (optionally substituted with one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals or C 1-6 -alkyl radicals), a C 3 -5-cycloalkyl-C 1-6 -alkyl (optionally substituted with one to three halogens or C 1-6 -alkyl), a C 3-5 -cycloalkylidene-C 1-6 -alkyl (optionally substituted with one to three halogen atoms or C 1-6 Alkyl radicals), a phenyl-C 1-6 -alkyl radical (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals) a phenyl-C 2-6 -alkenyl radical (optionally substituted with one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a 5 or 6-membered heterocyclic C 1-6 -alkyl radical (optionally subs substituted with one to three halogen atoms, C3-5 cycloalkyl radicals, C1-6 alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C1-6 alkyl radicals), a C1-6 alkoxy radical (optionally substituted with one to three Halogen atoms or C 1-6 -alkyl radicals), a C 3-6 -alkenyloxy radical (optionally substituted by one to three halogen atoms or C 1-6 -alkyl radicals), a C 3-6 -alkynyloxy radical (optionally substituted by one to three halogen atoms or C 1-6 -alkyl radicals) Alkyl radicals), a phenoxy group (optionally substituted with one to three halogen atoms, C3-5 cycloalkyl radicals, C1-6 alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C1-6 alkyl radicals), a C3-6 cycloalkyl C 1-6 alkoxy optionally substituted with one to three halogen atoms, a phenyl C 1-6 alkoxy (optionally substituted with one to three halogens, C 3-5 cycloalkyl, C 1-6 alkoxy, phenoxy, 5- or 6) -membered heterocyclic R5 or R6-) alkyl radicals, a 5- or 6-membered heterocyclic C1-6-alkoxy radical (optionally substituted by one to three halogen atoms, C3-5-cycloalkyl radicals, C1-6-alkoxy radicals, phenoxy groups, 5- or 6 heterocyclic or C1-6 alkyl groups), a C6-10 aryloxy C1-6 alkyl group (optionally substituted with one to three halogen atoms, C3-5 cycloalkyl groups, C1-6 alkoxy groups, phenoxy groups, or 5- or 6-membered heterocyclic oxo groups) and a 5- or 6-membered heterocyclic oxy-C 1-6 -alkyl group (optionally substituted with one to three halogen atoms, C 3-5 -cycloalkyl groups or C 1-6 -alkoxy groups)]; or a 3-pyrrolyl group whose N (nitrogen atom) is substituted with [a C 1-6 alkyl group (optionally substituted with one to three halogen atoms, C 3-5 cycloalkyl groups, C 1-6 alkoxy groups, phenoxy groups, 5- or 6-membered heterocyclic oxy groups or C1-6-alkyl radicals), a C2-6-alkenyl radical (optionally substituted by one to three halogen atoms, C3-5-cycloalkyl radicals, C1-6-alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxyreste or C1- 6-alkyl radicals), a C 2-6 -alkynyl radical (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a phenyl group (optionally substituted with one to three halogen atoms, C3-5 cycloalkyl groups, C1-6 alkoxy groups or C1-6 alkyl groups), a C3-5 cycloalkyl-C1-6 alkyl group (optionally substituted with one to three halogen atoms or C1-6 alkyl radicals), a C3 -5-cycloalkylidene-C 1-6 -alkyl (optionally substituted with one to three halogens or C 1-6 -alkyl), a phenyl-C 1-6 -alkyl (optionally substituted with one to three halogens, C 3-5 -cycloalkyl, C 1 -6-alkoxy, phenoxy, 5- or 6-membered heterocyclic oxy or C1-6-alkyl), a 5- or 6-membered heterocyclic C1-6-alkyl (optionally substituted with one to three halogen, C3-5-cycloalkyl , C 1-6 -alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a C 1-6 -alkoxy radical (optionally substituted by one to three halogen atoms or C 1-6 -alkyl radicals), a C 3 - 6-alkenyloxy (optionally substituted with one to three halogens or C1-6 alkyl), a C3-6 alkynyloxy (optionally substituted with one to three halogen atoms or C1-6 alkyl res thene), a phenoxy group (optionally substituted with one to three halogen atoms, C3-5 cycloalkyl radicals, C1-6 alkoxy radicals, phenoxy groups, 5- or 6-membered heterocyclic oxy radicals or C1-6 alkyl radicals), a C3-6 cycloalkyl C 1-6 alkoxy optionally substituted with one to three halogen atoms, a phenyl C 1-6 alkoxy (optionally substituted with one to three halogens, C 3-5 cycloalkyl, C 1-6 alkoxy, phenoxy, 5- or 6) heterocyclic oxy radicals or C 1-6 -alkyl radicals), a 5- or 6-membered heterocyclic C 1-6 -alkoxy radical (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals, C 1-6 -alkoxy radicals, phenoxy groups, or 6-membered heterocyclic oxy radicals or C 1-6 -alkyl radicals), a C 6-10 aryloxyC 1-6 alkyl radical (optionally substituted by one to three halogen atoms, C 3-5 cycloalkyl radicals, C 1-6 alkoxy radicals, phenoxy groups or 5 or 6-membered heterocyclic oxyres thene) or a 5- or 6-membered heterocyclic oxy-C 1-6 -alkyl radical (optionally substituted by one to three halogen atoms, C 3-5 -cycloalkyl radicals or C 1-6 -alkoxy radicals)].

In the present specification, examples of a halogen atom may include a fluorine atom, a chlorine atom and a bromine atom. Examples of a C1-6 alkyl group may include a methyl, ethyl, n-propyl, n-butyl, iso-butyl, n-pentyl, iso-pentyl, n-hexyl, 4-methylpentyl and 3-methylpentyl group. Examples of a C2-6 alkenyl group may include vinyl, allyl, 2-butenyl, 3-butenyl, 2-pentenyl, 3-pentenyl, prenyl, 3-methyl-3-butenyl, 2-hexenyl , 3-hexenyl, 4-hexenyl, 4-methyl-4-pentenyl and 4-methyl-3-pentenyl groups. Examples of a C 2-6 -alkynyl radical can be ethynyl, propargyl, 2-butynyl, 3-butynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl and 5-hexynyl group. Examples of a C3-8 cycloalkyl group may include a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl group. Examples of a C6-10 aryl group may include a phenyl, indenyl and naphthyl group. Examples of a 5- to 10-membered heterocyclic group may include a furyl, thienyl, pyridyl, benzofuranyl, benzothienyl, chromenyl, isocromenyl, thiocromenyl and isothiocromenyl group. Examples of a C 3-8 -cycloalkyl-C 1-6 -alkyl radical may include a cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclopropylbutyl, cyclopropylpentyl, cyclopropylhexyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclobutylbutyl, cyclobutylpentyl, cyclopentylethyl Cyclopentylpropyl, cyclopentylbutyl, cyclohexylethyl and cyclohexylpropyl groups. Examples of a C 3-8 cycloalkylidene-C 1-6 -alkyl radical may include a cyclopropylidenemethyl, cyclopropylidenethyl, cyclopropylidenepropyl, cyclopropylidenebutyl, cyclopropylidenepentyl, cyclopropylidenehexyl, cyclobutylidenemethyl, cyclobutylideneethyl, cyclobutylidenepropyl, cyclobutylidenebutyl, cyclobutylidenepentyl, cyclopentylideneethyl , Cyclopentylidenepropyl, cyclopentylidene-butyl, cyclohexylidene-ethyl and cyclohexylidene-propyl groups. Examples of a C6-10 aryl C1-6 alkyl group may include benzyl, phenethyl, phenylpropyl, phenylbutyl, phenylpentyl, 2-methyl-4-phenylbutyl, 2-methyl-5-phenylpentyl, 3 Methyl 5-phenylpentyl and (2-naphthyl) ethyl group. Examples of a 5 to 10 membered heterocyclic C 1-6 alkyl group may be a furylmethyl, furylethyl, furylpropyl, furylbutyl, furylpentyl, furylhexyl, thienylethyl, thienylmethyl, thienylpropyl, thienylbutyl, thienylpentyl and thienylhexyl group lock in. Examples of a C1-6 alkoxy group can be a methoxy, ethoxy, n-propyloxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, n-pentyloxy, iso-pentyloxy, sec-pentyloxy, n-hexyloxy, iso-hexyloxy, sec-hexyloxy and 2,3-dimethylbutoxy groups. Examples of a C 2-6 alkenyloxy group may include vinyloxy, allyloxy, 1-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 2-pentenyloxy, 3-pentenyloxy, prenyloxy, 3-methyl 3-butenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 4-methyl-4-pentenyloxy and 4-methyl-3-pentenyloxy. Examples of a C 2-6 alkynyloxy group may include propargyloxy, 2-butynyloxy, 3-butynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy and 5-hexynyloxy group. Examples of a C 3-8 cycloalkoxy group may include a cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy and cyclooctyloxy group. Examples of a C6-10 aryloxy group may include a phenoxy and naphthoxy group. Examples of a C 3-8 cycloalkyl-C 1-6 alkoxy group may be cyclopropylmethoxy, cyclopropylethoxy, cyclopropylpropoxy, cyclopropylbutoxy, cyclopropylpentyloxy, cyclopropylhexyloxy, cyclobutylmethoxy, cyclobutylethoxy, cyclobutylpropoxy, cyclobutylbutoxy, cyclobutylpentyloxy, cyclopentylethoxy , Cyclopentylpropoxy, cyclopentylbutoxy, cyclohexylethoxy and cyclohexylpropoxy groups. Examples of a C6-10 aryl-C1-6 alkoxy group may be benzyloxy, phenethyloxy, phenylpropyloxy, phenylbutyloxy, phenylpentyloxy, 2-methyl-4-phenylbutyloxy, 2-methyl-5-phenylpentyloxy, 3 Methyl 5-phenylpentyloxy and (2-naphthyl) ethyloxy groups. Examples of a 5 to 10 membered heterocyclic C 1-6 alkoxy group may include a furylmethoxy, furylethoxy, furylpropyloxy, furylbutyloxy, furylpentyloxy, furylhexyloxy, thienylmethoxy, thienylethoxy, thienylpropyloxy, thienylbutyloxy, thienylpentyloxy and thienylhexyloxy group lock in. Examples of a C1-6 alkylthio group may include a methylthio, ethylthio, n-propylthio, n-butylthio, iso-butylthio, n-pentylthio, iso-pentylthio, n-hexylthio, 4-methylpentylthio and 3-methylpentylthio group. Examples of a C 2-6 alkenylthio group may include a vinylthio, allylthio, 1-methyl-2-propenylthio, 2-butenylthio, 3-butenylthio, 2-pentenylthio, 3-pentenylthio, prenylthio, 3-Me thyl-3-butenylthio, 2-hexenylthio, 3-hexenylthio, 4-hexenylthio, 4-methyl-4-pentenylthio and 4-methyl-3-pentenylthio. Examples of a C 2-6 alkynylthio group may include propargylthio, 2-butynylthio, 3-butynylthio, 2-pentynylthio, 3-pentynylthio, 4-pentynylthio, 2-hexynylthio, 3-hexynylthio, 4-hexynylthio and 5-hexynylthio group. Examples of a C 3-8 cycloalkylthio group may include a cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cycloheptylthio and cyclooctylthio group. Examples of a C6-10 arylthio group may include a phenylthio and naphthylthio group. Examples of a C 3-8 -cycloalkyl-C 1-6 -alkylthio may include a cyclopropylmethylthio, cyclopropylethylthio, cyclopropylpropylthio, cyclopropylbutylthio, cyclopropylpentylthio, cyclopropylhexylthio, cyclobutylmethylthio, cyclobutylethylthio, cyclobutylpropylthio, cyclobutylbutylthio, cyclobutylpentylthio, cyclopentylethylthio , Cyclopentylpropylthio, cyclopentylbutylthio, cyclohexylethylthio and cyclohexylpropylthio groups. Examples of a C6-10 aryl C1-6 alkylthio group may include a benzylthio, phenethylthio, phenylpropylthio, phenylbutylthio, phenylpentylthio, 2-methyl-4-phenylbutylthio, 2-methyl-5-phenylpentylthio and 3-benzylthio. Methyl 5-phenylpentylthio group. Examples of a 5- to 10-membered C1-6-alkylthioalkyl heterocyclic group may include a furylmethylthio, furylethylthio, furylpropylthio, furylbutylthio, furylpentylthio, furylhexylthio, thienylethylthio, thienylmethylthio, thienylpropylthio, thienylbutylthio, thienylpentylthio and thienylhexylthio group lock in. Examples of a mono-C 1-6 -alkylamino group may include a methylamino, ethylamino, n-propylamino, n-butylamino, iso-butylamino, n-pentylamino, iso-pentylamino, n-hexylamino, 4-methylpentylamino and 3-methylpentylamino group. Examples of a mono-C 2-6 alkenylamino radical may be an allylamino, 2-butenylamino, 3-butenylamino, 2-pentenylamino, 3-pentenylamino, prenylamino, 3-methyl-3-butenylamino, 2-hexenylamino, , 3-hexenylamino, 4-hexenylamino, 4-methyl-4-pentenylamino and 4-methyl-3-pentenylamino groups. Examples of a mono-C 2-6 alkynylamino group may include propargylamino, 2-butynylamino, 3-butynylamino, 2-pentynylamino, 3-pentynylamino, 4-pentynylamino, 2-hexynylamino, 3-hexynylamino, 4 Hexynylamino and 5-hexynylamino group. Examples of a mono C 3-8 cycloalkylamino group may include a cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino and cyclooctylamino group. Examples of a mono-C6-10 arylamino group may include an alanyl group and a naphthylamino group. Examples of a mono-C 3-8 -cycloalkyl-C 1-6 -alkylamino radical may be a cyclopropylmethylamino, cyclopropylethylamino, cyclopropylpropylamino, cyclopropylbutylamino, cyclopropylpentylamino, cyclopropylhexylamino, cyclobutylmethylamino, cyclobutylethylamino, cyclobutylpropylamino, cyclobutylbutylamino, cyclobutylpentylamino, Cyclopentylethylamino, cyclopentylpropylamino, cyclopentylbutylamino, cyclohexylethylamino and cyclohexylpropylamino groups. Examples of a mono C6-10 aryl C1-6 alkylamino radical may include a benzylamino, phenethylamino, phenylpropylamino, phenylbutylamino, phenylpentylamino, 2-methyl-4-phenylbutylamino, 2-methyl-5-phenylpentylamino, 3-methyl-5-phenylpentylamino and (2-naphthyl) ethylamino group. Examples of a mono-5- to 10-membered heterocyclic C1-6-alkylamino group may be a furylmethylamino, furylethylamino, furylpropylamino, furylbutylamino, furylpentylamino, furylhexylamide, thienylethylamino, thienylmethylamino, thienylpropylamino, thienylbutylamino, thienylpentylamino, and thienylhexylamino group. Examples of a di-C 1-6 alkylamino group may include a dimethylamino, methylethylamino, diethylamino, methylpropylamino and methylbutylamino group. Examples of an N-C2-6 alkenyl-N-C1-6 alkylamino group may include N-allyl-N-methylamino, N- (2-butynyl) -N-methylamino and N- (3-butenyl) -N -methylamino group. Examples of an N-C2-6-alkynyl-N-C1-6-alkylamino group may include N-methyl-N-propargylamino, N- (2-butenyl) -N-methylamino and N- (3-butynyl) -N -methylamino group. Examples of an N-C3-8 cycloalkyl-N-C1-6 alkylamino group may include an N-cyclopropyl-N-methylamino, N-cyclobutyl-N-methylamino and N-cyclopentyl-N-methylamino group. An example of an N-C6-10 aryl-N-C1-6 alkylamino radical is an N-methylanilino group. Examples of an N-C3-8 cycloalkyl-C1-6-alkyl-N-C1-6 alkylamino group may include N-cyclopropylmethyl-N-methylamino, N-cyclopropylethyl-N-methylamino, N-cyclopropylpropyl-N-methylamino , N-cyclobutylmethyl-N-methylamino, N-cyclobutylethyl-N-methylamino and N-cyclobutylpropyl-N-methylamino group. Examples of an N-C6-10 aryl-C1-6-alkyl-N-C1-6-alkylamino group may include N-benzyl-N-methylamino, N-phenethyl-N-methylamino, N-phenylpropyl-N-methylamino , N-phenylbutyl-N-methylamino and N-phenylpentyl-N-methylamino group. Examples of an N-5 to 10-membered heterocyclic C 1-6 -alkyl-N-C 1-6 -alkylamino radical, C 1-6 -alkylcarbonyl radicals may be an N-furylmethyl-N-methylamino, N-furylethyl-N-methylamino, N-furylpropyl-N-methylamino, N-furylbutyl-N-methylamino, N-furylpentyl-N-methylamino, N-thienyl-N-methylamino, N-thienylethyl-N-methylamino, N-thienylpropyl-N -methylamino, N-thienylbutyl-N-methylamino and N-thienylpentyl-N-methylamino group. Examples of a C1-6 alkoxycarbonyl radical may include a methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxycarbonyl, sec-butoxycarbonyl, n-pentyloxycarbonyl, iso-pentyloxycarbonyl, sec-pentyloxycarbonyl, n-hexyloxycarbonyl, isohexyloxycarbonyl and sec-hexyloxycarbonyl groups. Examples of a C1-6 alkylsulfonyl group may include a methanesulfonyl, ethanesulfonyl, propanesulfonyl, butanesulfonyl, pentanesulfonyl and hexanesulfonyl group. Examples of a remainder of the formula -C (= NR ^a1 ) R ^a2 may include a hydroxyimonomethyl, hydroxyimonoethyl, methoxyiminomethyl, ethoxyiminomethyl and methoxyiminoethyl group. Examples of a C6-10 aryloxy C1-6 alkyl group may include a benzyloxymethyl, benzyloxyethyl, benzyloxypropyl, benzyloxybutyl, benzyloxypentyl and (2-naphthyl) oxymethyl group. Examples of a 5- to 10-membered heterocyclic oxy-C1-6-alkyl group may be a furyloxymethyl, furyloxyethyl, furyloxypropyl, furyloxybutyl, furyloxypentyl, thienyloxymethyl, thienyloxyethyl, thienyloxypropyl, thienyloxybutyl, thienyloxypentyl, pyridyloxymethyl , Pyridyloxyethyl, benzofuranyloxymethyl and benzothienyloxymethyl groups. Examples of a C6-10 aryl C2-6 alkenyl group may include a styryl group and a phenylpropenyl group.

more accurate Examples of such a radical E can be a phenyl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 5-phenyl-furan-2-yl, 5-phenoxy-furan-2-yl, 5- (4-fluorophenoxy) furan-2-yl, 5- (3-fluorophenoxy) furan-2-yl, 5- (4-methylphenoxy) furan-2-yl, 5- (4-chlorophenoxy) furan-2-yl, 5- (3-chlorophenoxy) furan-2-yl, 5- (3-methylphenoxy) furan-2-yl, 5- (4-methoxyphenoxy) furan-2-yl, 5- (3-methoxyphenoxy) furan-2-yl, 5-benzyl-furan-2-yl, 5- (4-fluorophenyl) -methyl-furan-2-yl, 5- (3-fluorophenyl) methyl-furan-2-yl, 5- (4-methylphenyl) methyl-furan-2-yl, 5- (4-chlorophenyl) methyl-furan-2-yl, 5- (3-chlorophenyl) methyl-furan-2-yl, 5- (3-methyl-phenyl) -methyl-furan-2-yl, 5- (4-methoxyphenyl) methyl-furan-2-yl, 5- (3-methoxyphenyl) methylfuran-2-yl, 5-phenoxythiophene-2-yl, 5- (4-fluorophenoxy) thiophene-2-yl, 5- (3-fluorophenoxy) thiophen-2-yl, 5- (2-fluorophenoxy) thiophen-2-yl, 5- (4-methylphenoxy) thiophen-2-yl, 5- (4-chlorophenoxy) thiophen-2-yl, 5- (3-chlorophenoxy) thiophen-2-yl, 5- (3-methylphenoxy) thiophen-2-yl, 5- (4-methoxyphenoxy) thiophen-2-yl, 5- (3-methoxyphenoxy) thiophen-2-yl, 5- (3-cyanophenoxy) thiophen-2-yl, 5-benzyloxythiophene-2-yl, 5-benzylthiophene-2-yl, 5- (4-fluorophenyl) methylthiophene-2-yl, 5- (3-fluorophenyl) methylthiophene-2-yl, 5- (4-methylphenyl) methylthiophene-2-yl, 5- (4-chlorophenyl) methylthiophene-2-yl, 5- (3-chlorophenyl) methylthiophene-2-yl, 5- (3-methylphenyl) methylthiophene-2-yl, 5- (3-methoxyphenyl) methylthiophene-2-yl, 5- (3-methoxyphenyl) methylthiophene-2-yl, 5- (2-thienyl) methylthiophene-2-yl, 5- (2-pyridyl) methylthiophene-2-yl, 5- (2-Benzofuranyl) methylthiophene-2-yl, 5-phenoxythiophene-3-yl, 5- (4-fluorophenoxy) thiophen-3-yl, 5- (3-fluorophenoxy) thiophen-3-yl, 5- (4-methylphenoxy) thiophen-3-yl, 5- (4-chlorophenoxy) thiophen-3-yl, 5- (3-chlorophenoxy) thiophen-3-yl, 5- (4-methylphenoxy) thiophen-3-yl, 5- (4-methoxyphenoxy) thiophen-3-yl, 5- (3-methoxyphenoxy) thiophen-3-yl, 3-isobutylphenyl, 3- (2-isobutenyl) phenyl, 3-isoprenyloxyphenyl, 3-cyclopentylmethylidenephenyl, 3-biphenyl, 3-benzylphenyl, 3-phenylaminophenyl, 3-phenylthiophenyl, 3-phenoxyphenyl, 3- (3-fluorophenoxy) phenyl, 3- (4-fluorophenoxy) phenyl, 3- (3-cyanophenoxy) phenyl, 3- (3-methoxyphenoxy) phenyl, 3- (3-fluorophenoxy) phenyl, 3-benzylaminophenyl, 3- (N -benzyl-N-methylamino) phenyl, 3-benzyloxyphenyl, 3- (3-methylbutoxy) phenyl, 3-cyclopropylmethoxyphenyl, 4-benzylphenyl, 4-phenoxyphenyl, 4-phenylthiophenyl, 4-benzyloxyphenyl, 4- (3-fluorobenzyloxy) phenyl, 4- (3-chlorobenzyloxy) phenyl, 4- (3-methylbenzyloxy) phenyl, 4- (3-methoxybenzyloxy) phenyl, 4- (2-pyridylmethyloxy) phenyl, 4- (2-furylmethoxy) phenyl, 4- (3-furylmethoxy) phenyl, 4- (2-thienylmethoxy) phenyl, 4- (3-thienylmethoxy) phenyl, 4- (5-benzo [1,3] dioxolylmethoxy) phenyl, 4- (6-fluoropyridin-2-yloxy) methylphenyl, 4-phenoxymethylphenyl, 4-phenethylphenyl, 4-benzylaminophenyl, 4- (N-benzyl-N-methylamino) phenyl, 4-phenylaminomethylphenyl, (Z) -4-styrylphenyl, 1-Benzylpyrrol-3-yl, 1-phenethylpyrrol-3-yl and 1- (5-benzo [1,3] dioxolyl) pyrrol-3-yl groups lock in.

A preferred example of the present compound is a compound wherein in formula (I) X represents a group of the formula [-C (= O) -NH-CH ₂ -], A represents a 6-quinolyl group, a [1.5] naphthyridine Represents 2-yl group or a benzothiazol-6-yl group; and E represents a 2-furyl, 2-thienyl, 3-pyrrolyl or phenyl group (wherein E may optionally have one or two substituents selected from the substituent group g-1 or Substituent group g-2).

More specific examples of the present compound are as shown in Table-1. No. A X e 1 6-quinolyl -C (= O) NHCH2- phenyl 2 6-quinolyl -C (= O) NHCH2- 4-benzyloxyphenyl 3 6-quinolyl -C (= O) NHCH2- 4-phenoxyphenyl 4 6-quinolyl -C (= O) NHCH2- 3-biphenyl 5 6-quinolyl -C (= O) NHCH2- 3-phenoxyphenyl 6 6-quinolyl -C (= O) NHCH2- 3-benzyloxyphenyl 7 6-quinolyl -C (= O) NHCH2- 3-hydroxyphenyl 8th 6-quinolyl -C (= O) NHCH2- 4-hydroxyphenyl 9 6-quinolyl -C (= O) NHCH2- 4-benzyloxy-2-fluorophenyl 10 6-quinolyl -C (= O) NHCH2- 4- (3-fluorobenzyloxy) phenyl 11 6-quinolyl -C (= O) NHCH2- 3- (4-fluorophenyl) oxyphenyl 12 6-quinolyl -C (= O) NHCH2- 3- (3-fluorophenyl) oxyphenyl 13 6-quinolyl -C (= O) NHCH2- 4- (1,3-dioxolidin-2-yl) phenyl 14 6-quinolyl -C (= O) NHCH2- 4- (2-phenyl) ethyl) phenyl 15 6-benzothiazolyl -NHC (= O) CH2- phenyl 16 6-quinolyl -C (= O) NHCH2- Three-cyclopropylmethoxyphenyl 17 6-quinolyl -C (= O) NHCH2- 4- (2-pyridyl) methoxyphenyl 18 6-quinolyl -C (= O) NHCH2- 3- (3-methylbutyloxy) phenyl 19 6-quinolyl -C (= O) NHCH2- 3-anilinophenyl 20 6-quinolyl -C (= O) NHCH2- 3-bromophenyl 21 6-quinolyl -C (= O) NHCH2- 4-benzylphenyl 22 6-quinolyl -C (= O) NHCH2- 3-benzylphenyl 23 6-quinolyl -C (= O) NHCH2- 3- (2-methyl-1-propenyl) phenyl 24 6-quinolyl -C (= O) NHCH2- 3- (2-methylpropyl) phenyl 25 6-quinolyl -NHC (= O) CH2- 4-phenoxyphenyl 26 6-quinolyl -NHC (= O) CH2- 3-methoxyphenyl 27 6-quinolyl -C (= O) NHCH2- 2-phenoxythiazol-5-yl 28 6-quinolyl -NHC (= O) CH2- 3-phenoxyphenyl 29 6-quinolyl -C (= O) NHCH2- 2- (5-phenoxy) thienyl 30 6-quinolyl -C (= O) NHCH2- 2- (5-phenoxy) thienyl 31 6-benzothiazolyl -C (= O) NHCH2- 4-benzyloxyphenyl 32 6-benzothiazolyl -C (= O) NHCH2- 3-phenoxyphenyl 33 6-benzothiazolyl -C (= O) NHCH2- phenyl 34 6-benzothiazolyl -C (= O) NHCH2- 4- (3-fluorobenzyloxy) phenyl 35 6-benzothiazolyl -C (= O) NHCH2- 2- [5- (3-fluorophenoxy)] thienyl 36 6-benzothiazolyl -C (= O) NHCH2- 2- (5-phenoxy) thienyl 37 6-benzothiazolyl -NHC (= O) CH2- 3-phenoxyphenyl 38 [1.5] naphthyridin-2yl -C (= O) NHCH2- 3-phenoxyphenyl 39 [1.5] naphthyridin-2yl -C (= O) NHCH2- 4-benzyloxyphenyl 40 6-quinolyl -C (= O) NHCH2- 4-methoxy-3-methylphenyl 41 6-quinolyl -C (= O) NHCH2- 3-chlorophenyl 42 6-quinolyl -C (= O) NHCH2- 2-thienyl 43 6-quinolyl -C (= O) NHCH2- 2-furyl 44 6-quinolyl -NHC (= O) CH2- 4-benzyloxyphenyl 45 6-quinolyl -NHC (= O) CH2- phenyl 46 6-quinolyl -C (= O) NHCH2- 3-thienyl 47 6-quinolyl -C (= O) NHCH2- 3-fluorophenyl 48 6-quinolyl -C (= O) NHCH2- 4-fluorophenyl 49 6-quinolyl -C (= O) NHCH2- 3-trifluoromethylphenyl 50 6-quinolyl -C (= O) NHCH2- 2- (5-phenoxy) thienyl 51 6-quinolyl -C (= O) NHCH2- 2,3-dimethoxyphenyl 52 6-quinolyl -NHC (= O) CH2- 2-fluorophenyl 53 6-quinolyl -C (= O) NHCH2- 2-methylphenyl 54 [1.5] naphthyridin-2yl -C (= O) NHCH2- 2- (5-phenoxy) thienyl 55 6-quinolyl -C (= O) NHCH2- 3-trifluoromethoxyphenyl 56 6-quinolyl -C (= O) NHCH2- 4-difluoromethoxyphenyl 57 6-quinolyl -C (= O) NHCH2- 4-ethoxyphenyl 59 6-quinolyl -C (= O) NHCH2- 2,4-difluorophenyl 60 6-quinolyl -C (= O) NHCH2- 2,5-difluorophenyl 61 6-quinolyl -C (= O) NHCH2- 3,5-difluorophenyl 62 6-quinolyl -C (= O) NHCH2- 2,6-difluorophenyl 63 6-quinolyl -C (= O) NHCH2- 3-methoxymethyl-phenyl 64 [1.5] naphthyridin-2yl -C (= O) NHCH2- 2-fluoro-3-cyclopropylmethoxyphenyl 65 6-quinolyl -C (= O) NHCH2- 2,3-difluorophenyl 66 6-quinolyl -C (= O) NHCH2- 5- (2-benzyloxy) thiazolyl 67 6-quinolyl -C (= O) NHCH2- 4- (2,4,6-trifluoro-benzyloxy) phenyl 68 6-quinolyl -C (= O) NHCH2- 3-benzyloxy-2-fluorophenyl 69 6-quinolyl -C (= O) NHCH2- 4- (2,4-difluoro-benzyloxy) phenyl 70 6-quinolyl -C (= O) NHCH2- 4-methoxymethylphenyl 71 6-quinolyl -C (= O) NHCH2- 3-ethoxymethylphenyl 72 6-quinolyl -C (= O) NHCH2- 4- (phenoxymethyl) phenyl 73 6-quinolyl -C (= O) NHCH2- 4-iso-propylphenyl 74 6-quinolyl -C (= O) NHCH2- 3-difluoromethoxyphenyl 75 6-quinolyl -C (= O) NHCH2- 4-methylthiophenyl 76 6-benzothiazolyl -C (= O) NHCH2- 3- (3-methyl-2-butenyloxy) phenyl 77 6-quinolyl -C (= O) NHCH2- 3-fluoro-4-phenoxyphenyl 78 6-quinolyl -C (= O) NHCH2- phenyl 3- (2-fluorophenoxy) 79 6-quinolyl -C (= O) NHCH2- phenyl 4- (3-fluorophenoxy) 80 6-quinolyl -C (= O) NHCH2- 2-fluoro-4-phenoxyphenyl 81 6-quinolyl -C (= O) NHCH2- 2- [5- (3-fluorobenzyl)] furyl 82 6-quinolyl -C (= O) NHCH2- 3- (2-phenylethyl) phenyl 83 7-fluoro-6-quinolyl -C (= O) NHCH2- phenyl 84 7-fluoro-6-quinolyl -C (= O) NHCH2- 2-fluorophenyl 85 7-fluoro-6-quinolyl -C (= O) NHCH2- 3-phenoxyphenyl 86 7-fluoro-6-quinolyl -C (= O) NHCH2- 4-benzyloxyphenyl 87 6-quinolyl -C (= O) NHCH2- 5- (1-butyl) -tetrazolyl 88 6-quinolyl -C (= O) NHCH2- 3- (4-methoxyphenoxy) phenyl 89 6-quinolyl -C (= O) NHCH2- 4- (2,4-difluorophenoxymethyl) phenyl 90 6-quinolyl -C (= O) NHCH2- 3- (3-methyl-2-butenyloxy) phenyl 91 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (2-methyl-2-butenyloxy) phenyl 92 2-methyl-6-quinolyl -C (= O) NHCH2- 3-phenoxyphenyl 93 8-fluoro-6-quinolyl -C (= O) NHCH2- phenyl 94 8-fluoro-6-quinolyl -C (= O) NHCH2- 2-fluorophenyl 95 8-fluoro-6-quinolyl -C (= O) NHCH2- 3-phenoxyphenyl 96 6-quinolyl -C (= O) NHCH2- 4- (3,4-difluoro-benzyloxy) phenyl 97 6-quinolyl -C (= O) NHCH2- 3- (2-fluorobenzyloxy) phenyl 98 6-quinolyl -C (= O) NHCH2- 3- (4-fluorobenzyloxy) phenyl 99 6-quinolyl -C (= O) NHCH2- 3- (3-phenylpropyloxy) phenyl 100 6-quinolyl -C (= O) NHCH2- 4- (4-pyridylmethoxy) phenyl 101 6-quinolyl -C (= O) NHCH2- 5-benzyloxy-2-fluorophenyl 102 6-quinolyl -C (= O) NHCH2- 3-methoxyethylphenyl 103 6-quinolyl -C (= O) NHCH2- 4- (2-phenylethoxy) phenyl 104 6-quinolyl -C (= O) NHCH2- 2-fluoro-5-methoxyphenyl 105 6-quinolyl -C (= O) NHCH2- 2-fluoro-4-methylphenyl 106 6-quinolyl -C (= O) NHCH2- 3-fluoro-4-methylphenyl 107 6-quinolyl -C (= O) NHCH2- 3-methyl-4-methoxyphenyl 108 6-quinolyl -C (= O) NHCH2- 3-methylthiophenyl 109 6-quinolyl -C (= O) NHCH2- 3-iso-propyloxyphenyl 110 6-quinolyl -C (= O) NHCH2- 3- (2-methylpropyloxy) phenyl 111 6-quinolyl -C (= O) NHCH2- 4-n-propyloxyphenyl 112 6-quinolyl -C (= O) NHCH2- 4-n-butyloxyphenyl 113 6-quinolyl -C (= O) NHCH2- 4-n-pentyloxyphenyl 114 6-quinolyl -C (= O) NHCH2- 4-n-hexyloxyphenyl 115 6-quinolyl -C (= O) NHCH2- 2-fluoro-4-phenoxymethylphenyl 116 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (3-methylbutyloxy) phenyl 117 6-quinolyl -C (= O) NHCH2- 3-bromo-2-fluorophenyl 118 6-quinolyl -C (= O) NHCH2- 3-cyclopropyl-phenyl 119 6-quinolyl -C (= O) NHCH2- 4-chloro-2-fluorophenyl 120 6-quinolyl -C (= O) NHCH2- 2-fluoro-4-pentyloxyphenyl 121 [1.5] naphthyridin-2yl -C (= O) NHCH2- 3-benzylphenyl 122 6-quinolyl -C (= O) NHCH2- 3- (3-ethoxycarbonylpropyloxy) phenyl 123 6-quinolyl -C (= O) NHCH2- 3-cyclobutylmethoxyphenyl 124 6-quinolyl -C (= O) NHCH2- 5-ethoxy-2-fluorophenyl 125 6-quinolyl -C (= O) NHCH2- 2-fluoro-5-n-propyloxyphenyl 126 6-quinolyl -C (= O) NHCH2- 5-n-butyloxy-2-fluorophenyl 127 6-quinolyl -C (= O) NHCH2- 2-fluoro-5-n-hexyloxyphenyl 128 6-quinolyl -C (= O) NHCH2- 2-fluoro-5-phenoxyphenyl 129 6-quinolyl -C (= O) NHCH2- 2-fluoro-3-phenoxyphenyl 130 6-quinolyl -C (= O) NHCH2- 3- (4-methylpentyloxy) phenyl 131 6-quinolyl -C (= O) NHCH2- 2-fluoro-3-hydroxyphenyl 132 [1.5] naphthyridin-2yl -C (= O) NHCH2- 4-benzylphenyl 133 [1.5] naphthyridin-2yl -C (= O) NHCH2- 4- (2-phenylethyl) phenyl 134 [1.5] naphthyridin-2yl -C (= O) NHCH2- 3-fluorophenyl 135 6-quinolyl -C (= O) NHCH2- 2-fluoro-3-cyclopropylmethoxyphenyl 136 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (3-phenylpropyloxy) phenyl 137 6-quinolyl -C (= O) NHCH2- 4- (4-fluorobenzyloxy) -2-fluorophenyl 138 [1.5] naphthyridin-2yl -C (= O) NHCH2- 4-fluorophenyl 139 6-quinolyl -C (= O) NHCH2- 4- (4-methylphenoxy) phenyl 140 6-quinolyl -C (= O) NHCH2- 3- (4-methylphenoxy) phenyl 141 6-quinolyl -C (= O) NHCH2- 3- (4-phenylbutyloxy) phenyl 142 6-quinolyl -C (= O) NHCH2- 4-fluoro-3-methoxyphenyl 143 6-quinolyl -C (= O) NHCH2- 2-chloro-5-thienyl 144 6-quinolyl -C (= O) NHCH2- 3- (3-chloro-2-propenyloxy) phenyl 145 6-quinolyl -C (= O) NHCH2- 5-methyl-2-thienyl 146 6-quinolyl -C (= O) NHCH2- 3- (3,3-dichloro-2-propenyloxy) phenyl 147 6-quinolyl -C (= O) NHCH2- 3- (2-chloro-2-propenyloxy) phenyl 148 6-quinolyl -C (= O) NHCH2- 5-methoxy-2-thienyl 149 6-quinolyl -C (= O) NHCH2- 3- (2-tetrahydrofuryl) methoxyphenyl 150 6-quinolyl -C (= O) NHCH2- 3- (3-cyanopropyloxy) phenyl 151 6-quinolyl -C (= O) NHCH2- 3,5-dimethoxyphenyl 152 [1.5] naphthyridin-2yl -C (= O) NHCH2- 2,5-difluorophenyl 153 6-benzothiazolyl -C (= O) NHCH2- 2-fluorophenyl 154 6-quinolyl -C (= O) NHCH2- 2-benzyl-5-tetrazolyl 155 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (2-methylpropyloxy) phenyl 156 6-quinolyl -C (= O) NHCH2- 3-iodophenyl 157 6-quinolyl -C (= O) NHCH2- 2-n-butyloxy-5-thiazolyl 158 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (4-phenylbutoxy) phenyl 159 6-quinolyl -C (= O) NHCH2- 3-ethynylphenyl 160 6-quinolyl -C (= O) NHCH2- 2-fluoro-3-methylphenyl 161 6-quinolyl -C (= O) NHCH2- 3- [2- (2-methoxyethoxy) ethoxy] phenyl 162 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- [2- (2-methoxyethoxy) ethoxy] phenyl 163 6-quinolyl -C (= O) NHCH2- 3-ethynyl-2-fluorophenyl 164 6-quinolyl -C (= O) NHCH2- 3- (3-methoxyphenoxy) phenyl 165 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (6-methoxyhexyloxy) phenyl 166 6-quinolyl -C (= S) NHCH2- 2-fluoro-3-methoxyphenyl 167 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (3,3-dichloro-2-propenyloxy) phenyl 168 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (3-chloro-2-propenyloxy) phenyl 169 6-quinolyl -C (= O) NHCH2- 2-fluoro-3- (2-chloro-2-propenyloxy) phenyl 170 6-quinolyl -C (= O) NHCH2- 4-methoxyphenyl 171 6-quinolyl -C (= O) NHCH2- 1- (3-fluorobenzyl) -3-pyrolyl 172 6-quinolyl -C (= O) NHCH2- phenyl 4- (4-fluorophenoxy) 173 6-quinolyl -C (= O) NHCH2- 4-fluoro-3-phenoxyphenyl 174 6-quinolyl -C (= O) NHCH2- 4- (4-fluorobenzyloxy) phenyl 175 6-benzothiazolyl -C (= O) NHCH2- 2-fluorophenyl 176 2-methyl-6-benzothiazolyl -C (= O) NHCH2- phenyl 177 2-methyl-6-benzothiazolyl -C (= O) NHCH2- 2-fluorophenyl 178 6-benzothiazolyl -C (= O) NHCH2- phenyl 3- (2-fluorophenoxy) 179 6-benzothiazolyl -C (= O) NHCH2- phenyl 3- (3-fluorophenoxy) 180 6-benzothiazolyl -C (= O) NHCH2- phenyl 3- (4-fluorophenoxy) 181 6-benzothiazolyl -C (= O) NHCH2- 3-n-pentylphenyl 182 6-benzothiazolyl -C (= O) NHCH2- 4-n-pentylphenyl 183 6-benzothiazolyl -C (= O) NHCH2- 4-fluoro-3-phenoxyphenyl 184 6-benzothiazolyl -C (= O) NHCH2- 2- [5- (3-cyanophenoxy)] thienyl 185 6-benzothiazolyl -C (= O) NHCH2- 3-methoxyphenyl 186 6-benzothiazolyl -C (= O) NHCH2- 2- [5- (3-fluorbenyl)] furyl 187 6-benzothiazolyl -C (= O) NHCH2- 2-methylphenyl 188 6-benzothiazolyl -C (= O) NHCH2- 3-methylphenyl 189 6-benzothiazolyl -C (= O) NHCH2- 4-methylphenyl 190 6-benzothiazolyl -C (= O) NHCH2- 3-hydroxyphenyl 191 6-benzothiazolyl -C (= O) NHCH2- 3-ethoxylphenyl 192 6-benzothiazolyl -C (= O) NHCH2- N-3-propyloxyphenyl 193 6-benzothiazolyl -C (= O) NHCH2- 3-n-butyloxyphenyl 194 6-benzothiazolyl -C (= O) NHCH2- 3-n-pentyloxyphenyl 195 6-benzothiazolyl -C (= O) NHCH2- 3-n-hexyloxyphenyl 196 6-benzothiazolyl -C (= O) NHCH2- 3-n-heptyloxyphenyl 197 6-benzothiazolyl -C (= O) NHCH2- 3-fluorophenyl 198 6-benzothiazolyl -C (= O) NHCH2- 4-fluorophenyl 199 6-benzothiazolyl -NHC (= O) CH2- 4-phenoxyphenyl 200 6-quinolyl -C (= O) NHCH2- 3- (ethoxyiminomethyl) phenyl 201 6-benzothiazolyl -NHC (= O) CH2- 3-benzyloxyphenyl 202 6-quinolyl -C (= S) NHCH2- 2-fluoro-3- (3-pent-4-ynyloxy) phenyl 203 6-benzothiazolyl -C (= O) NHCH2- 2- [5- (3-chlorophenoxy)] thienyl 204 6-quinolyl -C (= S) NHCH2- 4-benzyloxyphenyl 205 [1.5] naphthyridin-2yl -C (= S) NHCH2- 2-fluoro-3- (3-pent-4-ynyloxy) phenyl 206 6-benzothiazolyl -NHC (= O) CH2- 2-fluoro-3-methoxyphenyl 207 [1.5] naphthyridin-2yl -C (= O) NHCH2- phenyl 208 6-benzothiazolyl -C (= O) NHCH2- 3- (2-methylpropyl) phenyl 209 [1.5] naphthyridin-2yl -C (= O) NHCH2- 4-phenoxyphenyl 210 6-benzothiazolyl -C (= O) NHCH2- 3- (2-methylphenoxy) phenyl 211 6-benzothiazolyl -C (= O) NHCH2- 2-fluoro-3-hydroxyphenyl 212 6-benzothiazolyl -C (= O) NHCH2- 3- (3-methylphenoxy) phenyl 213 6-benzothiazolyl -C (= O) NHCH2- 3- (4-methylphenoxy) phenyl 214 6-benzothiazolyl -C (= O) NHCH2- 2-fluoro-3- (3-methylbutoxy) phenyl 215 6-benzothiazolyl -C (= O) NHCH2- 2-fluoro-3-n-propylphenyl 216 6-benzothiazolyl -C (= O) NHCH2- 2-fluoro-3-n-butylphenyl 217 6-benzothiazolyl -C (= O) NHCH2- 2-fluoro-3-n-pentylphenyl 218 6-benzothiazolyl -C (= O) NHCH2- 2-fluoro-3-n-hexylphenyl 219 6-benzothiazolyl -C (= O) NHCH2- 3- (3-methylbutyloxy) phenyl 220 6-benzothiazolyl -C (= O) NHCH2- 2-fluoro-3- (3-methyl-2-butenyloxy) phenyl 221 6-benzothiazolyl -C (= O) NHCH2- 2-fluoro-3- (2-methyl-1-propyloxy) phenyl 222 6-benzothiazolyl -NHC (= O) CH2- 4-methoxyphenyl 223 6-benzothiazolyl -NHC (= O) CH2- 3-methylphenyl 224 6-benzothiazolyl -NHC (= O) CH2- 4-methylphenyl 225 6-benzothiazolyl -NHC (= O) CH2- 2-fluorophenyl 226 6-benzothiazolyl -NHC (= O) CH2- 3-fluorophenyl 227 6-benzothiazolyl -NHC (= O) CH2- 4-fluorophenyl 228 [1.5] naphthyridin-2yl -C (= S) NHCH2- 2-fluoro-3-methoxyphenyl 229 6-benzothiazolyl -NHC (= O) CH2- 3- (3-methyl-2-butenyloxy) phenyl 230 6-benzothiazolyl -NHC (= O) CH2- 3- (3-methylbutyloxy) phenyl 231 6-quinolyl -NHC (= S) CH2 3-phenoxyphenyl

The present compound can be prepared by a manufacturing method disclosed in International Patent Application Laid-Open Publication No. Hei. WO2005 / 033079 (Patent Document 1), production processes described in the production examples given below, etc. are prepared.

at the agrochemical composition according to the invention In general, the present compound is mixed with a liquid Carrier, a solid carrier, a gas carrier, a surfactant, etc. mixed. After that Formulation aids, such as a binder or a thickener, if necessary, added so that the mixture becomes a wettable Powder, a granulated wettable powder, a flowable Means, a granulate, a dry flowable Means, an emulsion, an aqueous liquid Agent, an oil agent, a fumigant, a Aerosol, a microcapsule, etc. can be formulated, and the formulations thus prepared can then be used. The present compound is in such formulation in a weight ratio of generally between 0.1% and 99%, and preferably between 0.2% and 90%.

Examples of a liquid carrier, in a formulation include water, alcohols (eg, methanol, Ethanol, 1-propanol, 2-propanol, ethylene glycol, etc.), ketones (e.g. Acetone, methyl ethyl ketone, etc.), ethers (e.g., dioxane, tetrahydrofuran, Ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether etc.), aliphatic hydrocarbons (eg hexane, octane, cyclohexane, Coal oil, fuel oil, machine oil, etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, Methylnaphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, Chloroform, carbon tetrachloride, etc.), acid amides (e.g. Dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc.), Esters (eg ethyl acetate, butyl acetate, fatty acid glycerol esters etc.) and nitriles (e.g., acetonitrile, propionitrile, etc.). Two or more types of such liquid carriers mixed in a suitable ratio and then used become.

Examples a solid carrier used in the formulation include plant powders (eg soybean powder, Tobacco powder, wheat flour, wood flour, etc.), mineral powder (eg clays, such as kaolin, bentonite, sour clay or clay; Talke, like talcum powder or pyrophyllite powder; Silicas, such as diatomaceous earth or mica powder, etc.), alumina, sulfur powder, activated carbon, sugar (e.g. Lactose, glucose, etc.), inorganic salts (eg calcium carbonate, Sodium bicarbonate, etc.) and a glass hollow body (made by subjecting a natural holohyalin a combustion process and then encapsulating air bubbles therein) one. Two or more types of such solid carriers can be mixed in a suitable ratio and can then used. Such a liquid carrier or solid carrier is in a ratio of generally between about 1% to 99% by weight, and preferably between about 10% and 99% by weight, based on the total weight of the formulation, used.

When an emulsifier, a dispersing agent, a spreading agent, a penetrating agent, a humectant or the like used in the formulation In general, a surfactant is generally used. Examples of such a surfactant include anionic surfactants, such as alkyl sulfate ester salts, Alkylarylsulfonates, dialkylsulfosuccinates, polyoxyethylene-alkylaryl ether phosphates, Lignosulfonates or naphthalenesulfonate-formaldehyde polycondensates; and nonionic surfactants, such as Polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, a polyoxyethylene alkyl-polyoxypropylene block copolymer or a sorbitan fatty acid ester. These interface active Means can also be used in combination of two or more Species can be used. Such a surfactant is in a ratio of generally between 0.1% and 50% by weight, and preferably between about 0.1% and 25% by weight, based on the total weight of a formulation used.

Examples of a binder or thickener Dextrin, sodium salts of carboxymethylcellulose, a polycarboxylic acid polymer, Polyvinylpyrrolidone, polyvinyl alcohol, sodium lignosulphonate, calcium lignosulphonate, Sodium polyacrylate, gum arabic, sodium alginate, mannitol, sorbitol, Bentonite mineral substance, polyacrylic acid and a derivative thereof, sodium salts of carboxymethyl cellulose, white carbon black and natural ones Sugar derivatives (eg, xanthan gum, cyamopose gum, etc.).

Furthermore may be the agrochemical composition of the invention with other types of fungicides, insecticides, acaricides, nematocides, Herbicides, plant growth regulators, fertilizers or soil improvers, and they can be used. Otherwise, the present agrochemical Composition together with the abovementioned agents without Mixing can be used.

Examples of such other fungicides include: azoles such as propiconazole, prothioconazole, triadimol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluchinconazole, triticonazole, Bitertanol, imazalil, flutriafol, simeconazole or ipconazole; cyclic amines such as fenpropimorph, tridemorph or fenpropidin; Benzimidazoles, such as carbendazim, benomyl, thiabendazole or thio Phanat-methyl; procymidone; cyprodinil; pyrimethanil; diethofencarb; thiuram; Fluazinam, mancozeb; iprodione; Vinclozolin, chlorthalonil; captan; mepanipyrim; fenpiclonil; fludioxonil; dichlofluanid; folpet; Kresoxim-methyl; azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; metominostrobin; Enestrobin; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; Etaboxam; amisulbrom; iprovalicarb; benthiavalicarb; cyazofamid; Mandiproamid; boscalid; penthiopyrad; metrafenone; fluopyram; bixafen; cyflufenamid; Prochinazid; orysastrobin; furametpyr; thifluzamide; mepronil; flutolanil; flusulfamide; fluopicolid; Metalaxyl M; Kiralaxyl; fosetyl; cymoxanil; pencycuron; Trichlofos-methyl; carpropamid; diclocymet; fenoxanil; tricyclazole; pyroquilon; probenazole; isotianil; tiadinil; Tebuflochin; Flubuchin; Fluthianil; diclomezine; kasugamycin; ferimzone; phthalide; validamycin; hydroxyisoxazole; Iminoctadine acetate; isoprothiolane; oxolinic; oxytetracycline; streptomycin; basic copper chloride; Copper (II) hydroxide; basic copper sulfate; organic copper; and sulfur.

Examples the other insecticides include the following compounds one:

(1) Organophosphorus compounds

• Acephate, aluminum phosphide, butathiofos, cadusafos, Chloroethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, Cyanophos: CYAP, diazinon, dichlorodiisopropyl ether, dichlorofenthione: ECP, dichlorvos: DDVP, dimethoate, dimethylvinphos, disulfone, EPN, Ethion, Ethoprophos, Etrimfos, Fenthion: MPP, Fenitrothion: MEP, Fosthiazate, Formothion, Phosphine, Isofenphos, Isoxathione, Malathion, Mesulfenfos, Methidathion: DMTP, Monocrotophos, Naled: BRP, Oxydeprofos: ESP, parathion, phosalone, phosmet: PMP, pyrimiphos-methyl, pyridafenthione, Chinalphos, Phenthoat: PAP, Profenofos, Propaphos, Prothiofos, Pyrachlorfos, Salithion, Sulprofos, Tebupirimfos, Temephos, Tetrachlorvinphos, Terbufos, thiometon, trichlorophone: DEP, vamidothion, phorate, cadusafos and the like;

(2) carbamate compounds

• Alanycarb, Bendiocarb, Benfuracarb, BPMC, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Ethiofencarb, Fenobucarb, Fenothiocarb, fenoxycarb, furathiocarb, isoprocarb: MIPC, metolcarb, Methomyl, Methiocarb, NAC, Oxamyl, Pirimicarb, Propoxur: PHC, XMC, Thiodicarb, xylylcarb, aldicarb and the like;

(3) Synthetic pyrethroid compounds

• Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, Bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, Deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, Flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, Permethrin, prallethrin, pyrethrin, resmethrin, sigma-cypermethrin, Silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, Phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, furamethrin, tau-fluvalinate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzil (EZ) - (1RS, 3RS, 1RS, 3SR) -2,2-dimethyl-3-prop -1-enylcyclopropancarboxylat, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ) - (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropancarboxylat, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzil (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-cyclopropanecarboxylate 3- (2-methyl-1-propenyl) and the like;

(4) Nereistoxin compounds

• Cartap, Bensultap, Thiocyclam, Monosultap, Bisultap and the like;

(5) Neonicotinoid compounds

• Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, Thiacloprid, dinotefuran, clothianidin and the like;

(6) benzoylurea compounds

• Chlorfluazuron, Bistrifluron, Diafenthiuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, Triazuron and the like;

(7) phenylpyrazole compounds

• Acetoprol, ethiprole, fipronil, vaniliprole, Pyriprole, pyrafluprol and the like;

(8) Bt toxin insecticides

• Fresh spores, derived from Bacillus thuringiensis, crystalline toxins produced therefrom and mixtures thereof;

(9) hydrazine compounds

• Chromafenozide, halofenozide, methoxyfenozide, Tebufenozide and the like;

(10) organochlorine compounds

• Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor and the like;

(11) Natural insecticides

• Machine oil, nicotine sulfate;

(12) Other types of insecticides

• Avermectin B, bromopropylate, buprofezin, chlorphenapyr, Cyromazine, D-D (1,3-dichloropropene), emamectin benzoate, fenazachine, Flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, Pymetrozine, Pyralidyl, Pyriproxyfen, Spinosad, Sulfluramid, Tolfenpyrad, Triazamate, flubendiamide, lepimectin, arsenic acid, benclothiazole, Calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, Flonicamid, Flurimfen, Formetanat, Metam-Ammonium, Metam-Sodium, Methyl bromide, nidinotefuran, potassium oleate, protrifenobut, spiromesifen, Sulfur, metaflumizone, spirotetramat, pyrifluchinazone, spinetoram, Chlorantraniliprole.

Examples of other types of acaricides (acaricidal agents) include
Acechinocyl, amitraz, benzoximate, bifenaat, bromopropylate, quinomethionate, chlorobenzilate, CPCBS (chlorfenesone), clofentezine, cyflumetofen, kelthane (dicofol), etoxazole, fenbutazine oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargit: BPPS, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cyenopyrafen and the like.

Examples of other types of nematocides (nematocidal agents) include DCIP, Fosthiazate, levamisole hydrochloride, methyl isothiocyanate; Morant tartrate and imicyafos.

The Weight ratio between the invention agrochemical composition and a fungicide which has been described above said agrochemical composition mixed or together generally used is between 1: 0.01 and 1: 100, and preferably between 1: 0.1 and 1:10, with respect to the active ingredient.

The Weight ratio between the invention agrochemical composition and an insecticide containing the above agrochemical composition mixed or used together is generally between 1: 0.01 and 1: 100, and preferably between 1: 0.1 and 1:10, with respect to on the active ingredient.

The Weight ratio between the invention agrochemical composition and an acaricide, with the above said agrochemical composition mixed or together generally used is between 1: 0.01 and 1: 100, and preferably between 1: 0.1 and 1:10, with respect to the active ingredient.

The Weight ratio between the invention agrochemical composition and a nematocide associated with the above agrochemical composition mixed or used together is generally between 1: 0.01 and 1: 100, and preferably between 1: 0.1 and 1:10, with respect to on the active ingredient.

The Weight ratio between the invention agrochemical composition and a herbicide containing the above said agrochemical composition mixed or together generally used is between 1: 0.01 and 1: 100, and preferably between 1: 0.1 and 1:10, with respect to the active ingredient.

The weight ratio between the agrochemical composition of the invention and A plant growth regulator mixed with or used together with the above-mentioned agrochemical composition is generally between 1: 0.00001 and 1: 100, and preferably between 1: 0.0001 and 1: 1, in terms of the active ingredient.

The Weight ratio between the invention agrochemical composition and a fertilizer or Soil improver containing the aforementioned agrochemical Composition mixed or used together is generally between 1: 0.1 and 1: 1000 and preferably between 1: 1 and 1: 200, in terms of the active ingredient.

The Agrochemical composition according to the invention can be used to fight or prevent disease caused by phytopathogenic microbes, except Aspergillus, on agricultural land, such as fields, rice fields, Lawns or orchards.

The Type of a method of applying the invention agrochemical composition is not particularly limited provided that the agrochemical composition according to the invention can be applied essentially with the method. Examples of such application method include: application the present agrochemical composition on the plant body useful plants, such as foliar application; application of the present agrochemical composition on a field, in planted or planted useful plants are like earth treatment; and application of the present agrochemical Composition on seeds, such as seed sterilization.

A effective amount of the agrochemical invention Composition based on useful crops is applied, differs depending on one climatic condition, a dosage form, an application period, an application method, an application site, a target disease, Target crops, etc. With respect to the present invention, those in the agrochemical composition according to the invention is included, the effective amount is generally between 1 and 500 g and preferably 2 to 200 g, per 10 ares. A Emulsion, a wettable powder, a suspension, etc. are in Generally diluted for application with water. In one In such case, the concentration of present compound after dilution between 0.0005% and 2% by weight, and preferably between 0.005% and 1% by weight. on the other hand For example, a powder, granules, etc. are applied directly without they are diluted. When the agrochemical Composition applied to seeds is the present Compound present in the agrochemical Composition is included, in a range of generally between 0.001 and 100 g and preferably between 0.01 and 50 g, per kg of seeds, applied.

The Agrochemical composition according to the invention can fight or prevent diseases by Plant pathogenic microbes on agrochemical surfaces for Cultivating the following useful crops caused.

Examples of such useful crops are as follows.
Field crops: maize, rice, wheat, barley, rye, oats, sorghum, cotton, soybean, peanut, buckwheat, beetroot, rapeseed, sunflower, sugarcane, tobacco, etc .;
Vegetables: Solanaceae vegetables (eggplant, tomato, allspice, pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, squash, zucchini, watermelon, melon, etc.), Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, daisy, artichoke, lettuce, etc.), Liliaceae vegetables (green onion, onion, garlic and asparagus), Ammiaceae vegetables (carrot, parsley, Celery, parsnip, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Laminaceae vegetables (Perilla frutescens, mint, basil, etc.), strawberry, sweet potato, Dioscorea japonica, colocasia, etc., flowers, foliage plants; Fruits: Pomaceae fruits (apple, pear, Japanese pear, Chinese quince, quince, etc.), stonefruit (peach, plum, nectarine, prunus mume, cherry fruit, apricot, plum, etc.), citrus fruit (citrus unshiu, orange, lemon, Lime, grapefruit, etc.), nuts (chestnut, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon fruit, olive , Japanese plum, banana, coffee, date palm, coconuts, other trees than fruit trees; Tea, mulberry, flowering plants, trees along roads (ash, birch, dogwood, eucalyptus, ginkgo biloba, lilac, maple, quercus, poplar, judas tree, linquidambar formosana, "plane" tree, zelkova, japanese tree of life, fir wood, hemlock, Juniper, Pine, Picea and Taxus cuspidate) etc.

The above-mentioned "useful crops" include crops having resistance to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr or thifensulfuron-methyl, EP SP synthetase inhibitors, glutamine synthetase inhibitors, and herbicides such as bromoxynil, by a classical breeding method or genetic recombination.

Examples of "useful crops", which are resistant was awarded by a classical breeding process, close Clearfield (registered trademark) -Canola, resistant to imidazolinone herbicides, such as imazethapyr, is, and STS soybean resistant to sulfonylurea ALS inhibitor herbicides, such as thifensulfuron methyl. additionally close examples of "useful crops", which conferred resistance by genetic recombination becomes, cereals that are resistant to glyphosate or glufosinate. Such cereals are already with product names, such as "RoundupReady (registered trademark)" and "LibertyLink (registered trademark) "on the market.

The above-mentioned "useful crops" include genetically recombinant crops that produced using such genetic recombination methods which are capable of synthesizing selective toxins, which are known in the genus Bacillus.

Examples of the toxins present in such genetically recombinant crops expressed: insecticidal proteins, derived from Bacillus cereus or Bacillus popilliae; δ-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9, derived from Bacillus thuringiensis; insecticidal proteins, like VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived of nematodes; Toxins produced by animals, such as scorpiontoxin, Spider toxin, bee toxin or insect specific neurotoxins; toxins of molds; Vegetable lecithin; agglutinin; Protease inhibitors, such as trypsin inhibitor, a serine protease inhibitor, patatin, cystatin or a papain inhibitor; Ribosome inactivating proteins (RIP), such as lycin, corn RIP, abrin, luffin, saporin or briodin; Steroid-metabolizing Enzymes such as 3-hydroxysteroid oxidase, ecdysteroid UDP-glucosyltransferase, or cholesterol oxidase; an ecdysone inhibitor; HMG-COA reductase; Ion channel inhibitors, such as sodium channel inhibitor or calcium channel inhibitor; Juvenile hormone esterase; a diuretic hormone receptor; stilbene; bibenzyl synthase; chitinase; and glucanase.

Furthermore include toxins that are in such genetically recombinant Also expressed as: hybrid toxins of δ-endotoxin proteins, such as Cry1Ab, Cry1Ac, Cry1FF, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9, and insecticidal proteins, such as VIP1, VIP2, VIP3 or VIP3A; partially destroyed toxins; and modified toxins. Such hybrid toxins will become a new one Combination of different domains of such proteins produced using a genetic recombination method. As a partially destroyed toxin, Cry1Ab was known a destruction of part of an amino acid sequence having. A modified toxin is obtained by substitution of one or more amino acids from natural toxins produced.

Examples of such toxins and recombinant plants that are capable of synthesizing such toxins are in EP-A-0 374 753 . WO 93/07278 . WO 95/34656 . EP-A-0 427 529 . EP-A-451 878 . WO 03/052073 etc. described.

toxins, which are contained in such recombinant plants are for lending capable of resistance to the plants, especially towards Insect pests belonging to Coleoptera, Diptera and Lepidoptera.

Furthermore were genetically recombinant plants containing one or more insecticides pest-resistant genes include and one or more Toxins express, already known, and some of them genetically recombinant plants were already on the market. Examples of such genetically recombinant plants include YieldGard (registered Trademark) (a corn species for expressing Cry1Ab toxin), YieldGard Rootworm (registered trademark) (a type of corn to express of Cry3Bb1 toxin), YieldGard Plus (registered trademark) (a maize species expressing Cry1Ab and Cry3Bb1 toxins), Herculex I (Registered Trade Mark) (a corn species used to express Phosphinotricin N-acetyltransferase (PAT), so resistance conferring toxin and gluphosinate on Cry1Fa2), NuCOTN33B (a Cotton species for expressing Cry1Ac toxin), Bollgard I (registered Trademark) (a cotton species for expressing Cry1Ac toxin), Bollgard II (Trademark) (a cotton species to express of Cry1Ac and Cry2Ab toxins), VIPCOT (registered trademark) (a cotton species for expressing VIP toxin), NewLeaf (registered Trademark) (a potato for expressing Cry3A toxin), NatureGard (registered trademark) Agrisure (registered Trademark) Gt Advantage (GA21 Glyphosate Resistant Property), Agrisure (Registered Trademark) CB Advantage (Bt11 European corn borer (CB) property) and Protecta (registered trademark).

The above-mentioned "useful crops" also include crops using a genetically recombinant process are produced, the have the ability to antipathogenic substances with selective To produce effect.

A PR protein and the like were as such anti-pathogenic substances (PRP, EP-A-0 392 225 ) known. Such anti-pathogenic substances and genetically recombinant crops they produce are in EP-A-0 392 225 . WO 95/33818 . EP-A-0 353 191 etc. described.

Examples of such antipathogenic substances expressed in genetically recombinant crops include: Ion channel inhibitors such as a sodium channel inhibitor or a calcium channel inhibitor (KP1, KP4 and KP6 toxins, etc., which are formed by viruses were known); stilbene; bibenzyl synthase; chitinase; glucanase; a PR protein; and antipathogenic substances formed by microorganisms, such as a peptide antibiotic, an antibiotic having a hetero ring, a protein factor associated with plant disease resistance (which is called a plant resistance resistance gene), and WO 03/000906 is described).

Preferred examples of the plant pathogenic microbes which can be controlled by the present invention are phytopathogenic filamentous fungi other than Aspergillus. More specific examples include the following phytopathogenic microbes, but examples are not limited thereto. The names of the plant diseases and names of the plant pathogenic microbes are illustrated below: fire (Magnaporte grisea), Helminthosporium leaf spot (Cochliobolus miyabeanus), potato rootworm disease (Rhizoctonia solani), rice plant spleen disease (Gibberella fujikuroi) and rice powdery mildew (Sclerophthora macrospora) ; Powdery mildew (Erysiphe graminis), Fusarium head blight (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei) , Snow brandy (Typhula sp., Micronectriella nivalis), oatmeal (Ustilago tritici, U. nuda), wheat stain (Tilletia caries), eyespot (Pseudocercosporella herpotrichoides), brown spot (Rhynchosporium secalis), brown spot disease (Septoria tritici), glume spot disease (Leptosphaeria nodorum), brown spot (Pyrenophora teres Drechsler), take-all (Gaeumannomyces graminis) and brown spot (Pyrenophora tritici-repentis) of barley, wheat, oats and rye; melanosis (Diaporthe citri), scab (Elsinoe fawcetti) and penicillium Rot (Penicillium digitatum, P. italicum) of citrus;
Upholstery mold (Monilinia mali), jet rot (Valsa ceratosperma), mildew (Podosphaera leucotricha), Alternaria brown spot disease (Alternaria alternata apple pathotype), scab (Venturia inaequalis) and anthracnose (Glomerella cingulata) of apple; Scab (Venturia nashicola, V. pirina), brown spot disease (Alternaria alternata Japanese pear pathotype) and rust (Gymnosporangium haraeanum) of pear;
Poster mold (Monilinia fruticola), scab (Cladosporium carpophilum) and Phomopsis spot disease (Phomopsis sp.) Of peach;
Anthracnose (Elsinoe ampelina), anthracnose (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black spot disease (Guignardia bidwellii) and powdery mildew (Plasmopara viticola) of grapes;
Anthracnose (Gloeosporium kaki) and leaf spot disease (Cercospora kaki, Mycosphaerella nawae) from Japanese persimmon;
Anthracnose (Colletrotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), melon spot disease (Mycosphaerella melonis), wilting disease (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), Phytophthora fungal pathogens (Phytophtora sp.), And bed rot (Pythium sp.) pumpkin family;
Blight disease (Alternaria solani), brown spot disease (Cladosporium fulvum) and brown rot (Phytophthora infestans) from tomato;
Brown spot disease (Phomopsis vexans) and powdery mildew (Erysiphe cichoracearum) of eggplant;
Alternaria blight disease (Alternaria japonica), white spot disease (Cercosporella brassicae), cabbage hernia (Plasmodiophora parasitica) and downy mildew (Peronospora parasitica) of Cruciferae vegetables:
Rust (Puccinia allii) of winter onion;
Brown spot disease (Cercospora kikuchii), sphaceloma "scad" (Elsinoe glycines), root and stipe brandy (Diaporthe phaseolorum var. Sojae) and rust (Phakopsora pachyrhizi) of soybean;
Anthracnose (Colletotrichum lindemthianum) of kidney bean;
Leaf spot disease (Cercospora personata), brown eye disease (Cercospora arachidicola) and cancer (Sclerotium rolfsii) of peanut;
powdery mildew (Erysiphe pisi) of garden pea;
Brown spot disease (Alternaria solani), brown rot (Phytophthora infestans) and Verticillium wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens) of potato;
powdery mildew (Sphaerotheca humuli) of strawberry;
Bladder disease (Exobasidium reticulatum), white scab (Elsinoe leucospila), gray mold (Pestalotiopsis sp.) And anthracnose (Colletotrichum theae-sinensis) of tea;
Brown spots (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina) and brown rot (Phytophthora nicotinanae) of tobacco;
Cercospora leaf spot disease (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris) and Aphanomyces root rot (Aphanomyces sochlioides) of sugar beet;
Black spot disease (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa) of rose;
Leaf rot (Septoria chrysanthemi-indici) and white rust (Puccinia horiana) of chrysanthemum;
Stipe rot (Botrytis cinerea, B. byssoidea, B. squamosa), gray mold (Botrytis alli) and sclerotina stipe rot (Botrytis squamosa) of onion;
Gray mold (Botrytis cinerea) and Sclerotinia rot (Sclerotinia sclerotiorum) from various crops);
Alternaria leaf spot disease (Alternaria brassicicola) from Japanese radish;
Spot disease (Sclerotinia homeocarpa), brown spot disease and root gangrene (Rhizoctonia solani) of turf; and
Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola) of banana.

Examples

When Next, the present invention will be described in detail the following examples, the preparation examples, Formulation Examples, Test Examples, and the like. However, these examples are not intended to be limiting of Scope of the present invention.

Production Example 1

0.34 g 1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter abbreviated as WSC) were added to a mixture of 0.26 g of 6-quinolinecarboxylic acid, 0.16 g of benzylamine and 5 ml of pyridine. The resulting mixture was stirred at room temperature for 1.5 hours. After that was Water was added to the reaction mixture, followed by extraction with Ethyl acetate. The organic layer was washed successively with water and saturated sodium chloride, and it became then dried over anhydrous sodium sulfate, followed of concentrating under reduced pressure. The residue was subjected to silica gel column chromatography, whereby 0.26 g of N-benzyl-6-quinolinecarboxamide (1) was thus obtained.

N-benzyl-6-quinolinecarboxamide

• 1H-NMR (CDCl3) δ: 4.72 (2H, d, J = 5.6 Hz), 6.57 (1H, br s), 7.30-7.42 (5H, m), 7.47 (1H, dd, J = 8.3, 4.1 Hz), 8.07 (1H, dd, J = 8.8, 2.0 Hz), 8.15 (1H, d, J = 8.8 Hz), 8.23 (1H, d, J = 8.3 Hz), 8.33 (1H, d, J = 2.0 Hz), 8.99 (1H, dd, J = 4.1, 1.7 Hz).

The Products shown in Table-2 were as in Preparation Example 1 described produced.

Table 2 (NMR data)

When Next, formulation examples are listed below. It should be noted that the term "part" "part by weight" indicates.

Formulation Example 1

50 Parts of the present compound (1), 3 parts of calcium lignosulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic hydrous Silica was completely crushed and mixed so that wettable powders were obtained. The same above methods were carried out with the exception that the present compound (1) by one of the present Compounds (2) to (231) has been replaced, wherein so different Types of wettable powders were obtained.

Formulation Example 2

20 Parts of the present compound (1) and 1.5 parts of sorbitan trioleate were mixed to 28.5 parts of an aqueous solution, containing 2 parts of polyvinyl alcohol and the mixed solution was then a fine grinding according to a wet grinding method subjected. Thereafter, 40 parts of an aqueous solution, the 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate was added to obtain, and 10 parts of propylene glycol were added further added. The resulting mixture was stirred mixed, leaving such a flowable formulation was obtained. The same above methods were used with the Exception performed that the present compound (1) replaced by any one of the present compounds (2) to (231) became, whereby so different kinds of flowable Formulations were obtained.

Formulation Example 3

2 Parts of the present compound (1), 88 parts of kaolin clay and 10 Parts of talc were completely crushed and mixed, whereby a powder product was obtained. The same above Procedures were carried out with the exception that the present compound (1) by any of the present compounds (2) to (231), whereby various types of powder products were obtained.

Formulation Example 4

5 Parts of the present compound (1), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene were complete mixed, whereby an emulsion was obtained. The same above Procedures were carried out with the exception that the present compound (1) by any of the present compounds (2) to (231) has been replaced, thus providing various types of emulsions were obtained.

Formulation Example 5

2 Parts of the present compound (1), 1 part synthetic hydrous Silica, 2 parts calcium lignosulfonate, 30 parts bentonite and 65 parts of kaolin clay were completely crushed and mixed. Thereafter, water was added to the mixture and it became completely mixed, followed by granulation and drying, whereby such granules were obtained. The same above Procedures were carried out with the exception that the present compound (1) by any of the present compounds (2) to (231) has been replaced, whereby so different types of granules were obtained.

Formulation Example 6

Ten parts of the present compound (1), 35 parts of white carbon black containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salts and 55 parts of water were mixed, and the resulting mixture was then subjected to fine milling according to a wet milling method to give a flowable formulation was holding. The same procedures as above were carried out except that the present compound (1) was replaced by any one of the present compounds (2) to (231), thus obtaining various kinds of flowable formulations.

When Next, test examples are listed to show that the present invention for controlling Plant diseases is suitable.

Test Example 1

Test for the effects of prevention an infection by gray mold of cucumbers (Botrytis cinerea)

One Plastic pot was filled with sandy soil and cucumber (Variety: Sagami-Hanjiro) was then spread. They left the Cucumber growing in a hothouse 12 days. The above flowable Formulations containing the compounds 1, 2, 9, 12, 16, 18, 23, 24, 25, 26, 29, 30, 32, 36, 38, 39, 42, 43, 46, 47, 54, 60, 62, 64, 76, 77, 81, 90, 91, 95, 103, 105, 110, 116, 117, 118, 121, 123, 129, 132, 134, 135, 137, 145, 147, 148, 152, 155, 159, 185, 163, 164, 166, 171, 202, 204, 207, 208, 211, 219 were published fixed concentrations (500 ppm) by dilution with Water set and they were for a leaf application used so that they are sufficient on the leaves of the sticking cucumber plants could adhere. After complete Leaf application, the plants were air-dried. After that was Botrytis cinerea spore-containing PDA medium on the surface of the cotyledon. After such inoculation, the plants became stand at 12 ° C at high humidity for 5 days, and the infected areas thereof were then examined. As a result, it was found that the infected areas of the plants treated with the compounds 1, 2, 9, 12, 16, 18, 23, 24, 25, 26, 29, 30, 32, 36, 38, 39, 42, 43, 46, 47, 54, 60, 62, 64, 76, 77, 81, 90, 91, 95, 103, 105, 110, 116, 117, 118, 121, 123, 129, 132, 134, 135, 137, 145, 147, 148, 152, 155, 159, 185, 163, 164, 166, 171, 202, 204, 207, 208, 211, 219, 10% or less of the infected areas of the untreated Had plants.

Test Example 2

Test for the effects of prevention an infection by cucumber sclerotinia (Sclerotinia sclerotiorum)

A plastic pot was filled with sandy soil and cucumber (variety: Sagami-hanjiro) was then sprinkled. The cucumber was grown in a greenhouse for 12 days. The above flowable formulations containing the compounds 1, 2, 3, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 21, 22, 23, 24, 25, 26, 27, 29, 30, 33, 34, 35, 36, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 57, 59, 60, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 143, 144, 145, 146, 147, 148, 149, 151, 152, 153, 155, 156, 157, 159, 160, 158, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 183, 185, 188, 190, 199, 200, 201, 202, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231 were fixed Ko concentrations (500 ppm) were adjusted by diluting with water and they were used for foliar application so that they could sufficiently adhere to the leaves of the above cucumber plants. After complete leaf application, the plants were air-dried. Thereafter, Sclerotinia sclerotiorum hypha-containing PDA medium was applied to the surface of the cucumber leaf. After such seeding, the plants were allowed to stand at 18 ° C at high humidity for 4 days, and the infected areas thereof were then examined. As a result, it was found that the infected areas of the plants treated with the compounds 1, 2, 3, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 21, 22, 23, 24, 25, 26, 27, 29, 30, 33, 34, 35, 36, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 50, 52, 53, 54, 55, 57, 59, 60, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 115, 116, 117, 118, 119, 120, 121, 123, 124, 125, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 155, 156, 157, 159, 160, 158, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 180, 181, 183, 185, 190, 199, 200, 201, 202, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231 had been treated , 10% or less of the infected areas of untreated plants. The infected areas of the plants treated with compounds 49, 51, 92, 114, 126 and 188 were 30% or less infected areas of untreated plants.

Test Example 3

Test for the effects of prevention an infection by brown rot of tomato (Phytophtora infestans)

One Plastic pot was filled with sandy soil and tomato (Variety: Patio) was then spread. They left the tomato Grow in a hothouse for 20 days. The above-mentioned flowable Formulations comprising compounds 176 and 177 were to fixed concentrations (500 ppm) by dilution set with water and then they were for a foliar application used so that they are sufficient on the leaves of the stick to the above rearing tomato plants. The plants were subjected to air drying to such an extent that the diluted solution will dry on the sheet could. Thereafter, a Phytophthora infestans spore containing Water suspension on the rearing tomato plants by spraying inoculated. After complete inoculation the plants became First left at 23 ° C at high humidity for 1 day and then they were allowed to grow in a greenhouse for 4 days. Thereafter, the infected areas thereof were examined. As a result, it was found that the infected areas of the plants treated with compounds 176 and 177 were 10% or less of the infected areas of the untreated Plants were.

Test Example 4

Test for the effects of prevention infection by Fusarium headache in wheat (Fusarium culmorum)

One Plastic pot was filled with sandy soil and wheat (Variety: Shirogane) was then spread. One left the Wheat growing in a hothouse for 10 days. The above flowable formulation containing the compound (4) was measured to a fixed concentration (500 ppm) Diluted with water and then she was for used a sheet application so that they are sufficient to the Leaves of the above wheat plants could adhere. After complete foliar application, the plants became subjected to air drying. After that became a Fusarium culmorum spore containing water suspension on the wheat plants by spraying inoculated. After complete inoculation the plants became first at 23 ° C in high humidity on a dark Left for 4 days and then they were under lighting 3 days left. After that, the infected areas were examined. As a result, it was found that the infected Areas of plants treated with compound (4) 30% or less of the infected areas of the untreated plants were.

Test Example 5

Test for the effects of prevention an infection caused by fire in rice (Magnaporthe grisea)

One Plastic pot was filled with Einbetterde and rice (variety: Nihonbare) was then spread. The rice plants were left Grow in a greenhouse for 12 days. The above flowable Formulations comprising compounds 56, 122 and 161 have been reported to fixed concentrations (500 ppm) by dilution set with water, and they were for a leaf application used so that it sufficiently on the leaves of the above rice plants could be attached. After complete application of leaves the plants were air-dried. Then you left Pots, the leaves infected with fire in rice contained to stand the rice plants. All rice plants were left only stand at high humidity during the night. Five days after inoculation were the infected areas examined. As a result, it was found that the infected Areas of plants containing the compounds 121 and 161 were treated, 10% or less of the infected areas the untreated plants were and the areas of the plants, which were treated with Compound 56, 30% or less of the infected areas of the untreated areas were.

Test Example 6

Test for the effects of prevention an infection by sclerotinic disease in cucumbers through soil treatment (Sprinkling) (Sclerotinia sclerotiorum)

A plastic pot was filled with sandy soil and cucumber (variety: Sagami-hanjiro) was then out scattered. The cucumber plants were grown in a greenhouse for 12 days. The above flowable formulations containing the compounds 1, 33, 42, 48, 52, 60, 62, 65, 70, 74, 83, 84, 94, 105, 117, 118, 145, 159, 163, 170, 175, 176, 177, 185 and 207 were diluted with water and 1 mg of such compound was applied to the above pot by a soil irrigation treatment. After complete treatment, the plants were allowed to grow in a greenhouse for 1 week. Thereafter, Sclerotinia sclerotiorum hypha-containing PDA medium was applied to the leaves of the cucumber plants. After such inoculation, the plants were allowed to stand at 18 ° C at high humidity for 4 days, and the infected areas thereof were then examined. As a result, it has been found that the infected areas of the plants treated with the compounds 1, 33, 42, 48, 52, 60, 62, 65, 70, 74, 83, 84, 94, 105, 117, 118, 145, 159, 163, 170, 175, 176, 177, 185 and 207 had 10% or less of the infected areas of the untreated plants.

Test Example 7

Test for treatment effects of powdery mildew on grapes (Plasmopara viticola)

One Plastic pot was filled with sandy soil and grape (Variety: Berry-A) was then spread. One left the grape plants grow 40 days in a hothouse. A water suspension of zoosporangium Plasmopara viticola was sprayed onto the projecting pot inoculated. Then the grape plants were left at 23 ° C stand at high humidity for 1 day, and then they were air-dried, so that with real mildew of grape infected rearing plants were obtained. The above-mentioned flowable Formulation comprising compound 189 has been established Concentration (500 ppm) adjusted by dilution with water, and it was then subjected to foliar application such that they sufficiently on the leaves of the above rearing plants of grapes could be attached. After complete Leaf application, the plants were subjected to air drying, and then they were at 23 ° C in a hothouse 5 days ditched. Thereafter, the plants continued at 23 ° C high humidity for 1 day. After that, the infected ones became Surfaces examined. As a result, it was found that the infected areas of the plants that connect with 189 were treated, 10% or less of the infected areas of the untreated plants were.

Test Example 8

Test for the effects of prevention infection by tomato wilt through soil treatment (irrigation)

One Plastic pot is filled with soil, with tomato wilt (Fusarium oxysporum) is contaminated, and tomato (variety: Patio) is then spread. The above flowable Formulations comprising compounds 1 to 231 are diluted with water, and 10 mg of such a compound are applied to the projecting pot by soil irrigation treatment. The tomato plants are then left in a greenhouse Grow 1 month. Thereafter, the plants obtained are untreated Compared plants. As a result, it is found that no Stains on the plants treated with compounds 1 to 231 and that the treated plants are preferred in grow to a degree that is equal to that of the plants that are not in contaminated soil grew.

Test Example 9

One Plastic pot is filled with soil containing Verticillium wilt (Verticillium alboatrum, V. dahliae, V. nigrescens) is, and potato (variety: Danshaku) is then planted. The above flowable formulations containing the compounds 1 to 231 are diluted with water, and 10 mg of such a compound are passed through to the above pot applied a soil irrigation treatment. One lets the potato plants then grow in a hothouse for 2 months. Thereafter, the obtained plants with untreated plants compared. As a result, it is found that no stains on the plants treated with the compounds 1 to 231 found and that the untreated plants are preferred in one degree grow equal to that of the plants that are not contaminated Earth grow.

Test Example 10

The above flowable formulations comprising compounds 1 to 231 are seeded on husked rice contaminated with fungal disease of rice plant (Gibberella fujikuroi) treatment applied at a level of 200 g of each compound to 100 kg of the seeds. Then the rice plants are grown in a greenhouse for 1 month. Thereafter, the plants obtained are compared with untreated plants. As a result, it is found that the plants treated with the compounds 1 to 231 preferably grow at a level equal to that of the plants grown from uncontaminated husked rice.

Test Example 11

The above flowable formulations, the Compounds 1 to 231 are used on maltseeds with Malzwelke ("malt damping off", Gaeumannomyces graminis) contaminated by a seeding treatment to a degree of 200 g of each compound applied to 100 kg of the seeds. Then you leave the malt plants in a hothouse grow 1 month. After that will be compared the obtained plants with untreated plants. When Result, it is found that with the compounds 1 to 231 treated plants preferably grow to a degree equal to that of plants growing from uncontaminated crops.

Industrial applicability

According to the Present invention can provide plant diseases which by plant pathogenic microbes except Aspergillus become, be fought or prevented.

QUOTES INCLUDE IN THE DESCRIPTION

This list The documents listed by the applicant have been automated generated and is solely for better information recorded by the reader. The list is not part of the German Patent or utility model application. The DPMA takes over no liability for any errors or omissions.

Cited patent literature

• WO 2005/033079 [0003, 0020]
• EP 0 374 753 A [0048]
• - WO 93/07278 [0048]
• WO 95/34656 [0048]
• EP 0427529 A [0048]
• - EP 451878 A [0048]
• WO 03/052073 [0048]
• - EP 0392225 A [0052, 0052]
• WO 95/33818 [0052]
• EP 0353191 A [0052]
• WO 03/000906 [0053]

Claims (12)

An agrochemical composition for controlling plant diseases caused by plant pathogenic microbes other than Aspergillus comprising a compound of the formula (I), a salt thereof or a hydrate thereof: Formula (I)

wherein A represents a benzothiazol-6-yl group; X is a radical of the formula -NH-C (= Y) -CH ₂ - or a radical of the formula -C (= Y) -NH-CH ₂ -; Y represents an oxygen atom, a sulfur atom or NR ^Y , wherein R ^{Y represents} a C 1-6 alkoxy group or a cyano group; and E represents a furyl group, a thienyl group, a pyrrolyl group, a tetrazolyl group, a thiazolyl group, a pyrazolyl group or a phenyl group; wherein A may optionally have one to three substituents selected from the following substituent group a-1 and substituent group a-2, and E may optionally have one or two substituents selected from the following substituent group a-1 and substituent group a-2: [Substituent group a-1] halogen, hydroxyl, mercapto, cyano, carboxyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-8 cycloalkyl, C 6-10 aryl, 5-10-membered heterocyclic group, C 3-8 cycloalkyl-C 1-6 alkyl group, C 3-8 cycloalkylidene C 1-6 alkyl group, C 6-10 aryl C 1-6 alkyl group, C 6-10 aryl C 2-6 alkenyl group , 5- to 10-membered heterocyclic C1-6-alkyl group, C1-6-alkoxy group, C2-6-alkenyloxy group, C2-6-alkynyloxy group, C3-8-cycloalkoxy group, C6-10-aryloxy group, C-3-8- Cycloalkyl-C 1-6 -alkoxy, C 6-10 -aryl-C 1-6 -alkoxy, 5-10-membered heterocyclic C 1-6 -alkoxy, C 1-6 -alkylthio, C 2-6 -alkenylthio, C 2-6 -alkynylthio , C3-8-C cycloalkylthio, C6-10-arylthio, C3-8 -cycloalkyl-C1-6-alkylthio, C6-10-aryl-C1-6-alkylthio, 5-10-membered heterocyclic C1-6-alkylthio, mono-C1-6 -alkylamino, mono-C2-6-alkenylamino, mono-C2-6-alkynylamino, mono-C3-8-cycloalkylamino, mono-C6-10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono -C6-10-aryl-C1-6-alkylamino, mono-5- to 10-membered heterocyclic C1-6-alkylamino, di-C1-6-alkylamino, N-C2-6-alkenyl-N-C1-6- alkylamino, N-C2-6-alkynyl-N-C1-6-alkylamino, N-C3-8-cycloalkyl-N-C1-6-alkylamino, N-C6-10-aryl-N-C1-6-alkylamino, N-C3-8 cycloalkyl-C1-6-alkyl-N-C1-6 alkylamino, N-C6-10 aryl-C1-6-alkyl-N-C1-6-alkylamino, N-5-10 heterocyclic C1-6-alkyl-N-C1-6-alkylamino, C1-6-alkylcarbonyl, C1-6-alkoxycarbonyl, C1-6-alkylsulfonyl, a radical of the formula -C (= NR ^a1 ) R ^a2 (where R ^{a1 represents} a hydroxyl group or a C 1-6 alkoxy group; and R ^{a2 represents} a hydrogen atom or a C 1-6 alkyl group), C 6-10 aryloxy C 1-6 alkyl group and 5-10 membered heterocyclic oxy C 1-6 alkyl group; and [Substituent Group a-2] C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 3-8 -cycloalkyl, C 6-10 -aryl, 5-10-membered heterocyclic, C 3-8 -alkyl Cycloalkyl-C 1-6 -alkyl, C 6-10 -aryl-C 1-6 -alkyl, 5-10-membered C 1-6 -heterocyclic, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy , C 3-8 -cycloalkoxy, C 6-10 -aryloxy, C 3-8 -cycloalkyl-C 1-6 -alkoxy, C 6-10 -aryl-C 1-6 -alkoxy, 5-10-membered heterocyclic C 1-6 6-alkoxy, C1-6-alkylthio, C2-6-alkenylthio, C2-6-alkynylthio, C3-8 -cycloalkylthio, C6-10-arylthio, C3-8-cycloalkyl-C1-6-alkylthio, C6-10- Aryl C 1-6 alkylthio, 5-10 membered heterocyclic C 1-6 alkylthio, mono C 1-6 alkylamino, mono C 2-6 alkenylamino, mono C 2-6 alkynylamino, mono C 3-8 -cycloalkylamino, mono-C6-10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono-C6-10-aryl-C1-6-alkylamino, mono-5- to 10-membered heterocyclic C1- 6-alkyla minor, di-C1-6-alkylamino, N-C2-6-alkenyl-N-C1-6-alkylamino, N-C2-6-alkynyl-N-C1-6-alkylamino, N-C3-8-cycloalkyl N-C 1-6 -alkylamino, N-C 6-10 -aryl-N-C 1-6 -alkylamino, N-C 3-8 -cycloalkyl-C 1-6 -alkyl-N-C 1-6 -alkylamino, N-C 6 10-aryl-C 1-6 -alkyl-N-C 1-6 -alkylamino, N-5-10-membered heterocyclic C 1-6 -alkyl-N-C 1-6 -alkylamino, C 6-10 aryloxy-C 1-6 alkyl and 5- to 10-membered heterocyclic oxy-C1-6-alkyl; wherein each group described in the substituent group a-2 has one to three substituents selected from the following substituent group b: [Substituent group b] halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 Alkyl, C3-8 cycloalkyl, C6-10 aryl, 5-10 membered heterocyclic C 1-6 alkoxy, C 6-10 aryloxy, 5-10 membered heterocyclic oxy, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfonyl, trifluoromethyl, trifluoromethoxy, mono C 1-6 alkylamino, Di-C 1 -6-alkylamino, mono-C6-10-arylamino, optionally having an amino group or an aminosulfonyl group, and N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino, optionally having an amino group , An agrochemical composition according to claim 1, wherein in the formula (I), A represents a benzothiazol-6-yl group (wherein A may optionally have one to three substituents selected from the following substituent group c-1 and substituent group c-2): [Substituent group c -1] halogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-8-cycloalkyl, C6-10-aryl, 5-10-membered heterocyclic, C3-8-cycloalkyl C 1-6 -alkyl, C 6-10 -aryl-C 1-6 -alkyl, C 6-10 -aryl-C 2-6 -alkenyl, C 5-10-membered heterocyclic C 1-6 -alkyl, C 1-6 -alkoxy, C 2-6 -6-alkenyloxy, C2-6-alkynyloxy, C3-8-cycloalkyl-C1-6-alkoxy, C6-10-aryl-C1-6-alkoxy, 5-10-membered heterocyclic C1-6-alkoxy, mono- C2-6-alkylamino, mono C3-8 alkenylamino, mono C6-10 alkynylamino, mono C3-8 cycloalkylamino, mono C1-6 arylamino, mono C6-10 cycloalkyl C1-6 alkylamino radical, mono-C 1-6 -aryl-C 1-6 -alkylamino radical, mono-5- to 10-membered he terocyclic C 1-6 -alkylamino radical, C 2-6 -alkylcarbonyl radical and a radical of the formula -C (= N-OH) R a ² (where R a ^{2 has} the meanings given above); and [Substituent group c-2] C 1-6 -alkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, C 3-8 -cycloalkyl, C 6-10 -aryl, 5-10-membered heterocyclic, C 3-8 -alkyl Cycloalkyl-C 1-6 -alkyl, C 6-10 -aryl-C 1-6 -alkyl, 5-10-membered C 1-6 -heterocyclic, C 1-6 -alkoxy, C 2-6 -alkenyloxy, C 2-6 -alkynyloxy , C 3-8 -cycloalkyl-C 1-6 -alkoxy, C 6-10 -aryl-C 1-6 -alkoxy, 5-10-membered heterocyclic C 1-6 -alkoxy, mono-C 1-6 -alkylamino, mono-C 2- 6-alkenylamino, mono-C2-6-alkynylamino, mono-C3-8-cycloalkylamino, mono-C6-10-arylamino, mono-C3-8-cycloalkyl-C1-6-alkylamino, mono-C6-10-aryl C 1-6 alkylamino and mono 5- to 10-membered heterocyclic C 1-6 alkylamino (wherein each of the groups described in C-2 has one to three substituents selected from the following substituent group d): [Substituent group d] The halogen atom , Hydroxyl group, carboxyl group, amino group, carbamoyl group, C 1-6 alkoxy mono-C 1-6 -alkylamino, di-C 1-6 -alkylamino, mono C 6-10 arylamino, optionally having an amino group or an aminosulfonyl group, N-C 6 -10 aryl-C 1-6 -alkyl-N -C1-6-alkylamino radical optionally having an amino group, cyano group, C6-10-aryl radical, 5-10-membered heterocyclic radical and C1-6-alkoxycarbonyl radical. An agrochemical composition according to claim 1 or 2, wherein in formula (I) X represents a radical of the formula [-C (= O) -NH-CH ₂ -]. Agrochemical composition according to one of the claims 1 to 3, wherein in the formula (I) E is a furyl group, thienyl group, Pyrrolyl group or phenyl group (where E is optionally one or two substituents selected from the substituent group a-1 and the substituent group a-2). An agrochemical composition according to any one of claims 1 to 3, wherein in the formula (I) E represents a furyl group, thienyl group, pyrrolyl group or phenyl group (wherein E may optionally have one or two substituents selected from the following substituent group e-1 and substituent group e- 2): [Substituent group e-1] halogen atom, C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C6-10 aryl group, C3-8 cycloalkyl-C1-6 alkyl group, C3-8 -Cycloalkylidene-C 1-6 -alkyl, C 6-10 -aryl-C 1-6 -alkyl, C 6-10 -aryl-C 2-6 -alkenyl, 5-10-membered heterocyclic C 1-6 -alkyl, C 1-6 -alkyl Alkoxy, C2-6 alkenyloxy, C2-6 alkynyloxy, C6-10 aryloxy, C3-8 cycloalkyl C1-6 alkoxy, C6-10 aryl C1-6 alkoxy, 5-10 membered heterocyclic C1-6 alkoxy, C6-10 arylthio, C6-10 aryl C1-6 alkylthio, mono C6-10 arylamino, mono C6-10 aryl C1-6 alkylamino, N-C6 -10-aryl-N-C1-6-alkylamino, N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino, C6 -10-aryloxy-C1-6-alkyl and 5- to 10-membered heterocyclic oxy-C1-6-alkyl; and [Substituent Group e-2] C 1-6 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 6-10 aryl group, C 3-8 cycloalkyl-C 1-6 alkyl group, C 6-10 aryl-C 1- -6-alkyl, 5- to 10-membered heterocyclic C1-6-alkyl, C1-6-alkoxy, C2-6-alkeny loxyl, C2-6 alkynyloxy, C6-10 aryloxy, C3-8 cycloalkyl C1-6 alkoxy, C6-10 aryl C1-6 alkoxy, 5-10 member heterocyclic C1-6 alkoxy C6-10 arylthio, C6-10 aryl C1-6 alkylthio, mono C6-10 arylamino, mono C6-10 aryl C1-6 alkylamino, N-C6-10 aryl N C1-6-alkylamino, N-C6-10-aryl-C1-6-alkyl-N-C1-6-alkylamino, C6-10-aryloxy-C1-6-alkyl and 5-10-membered heterocyclic oxyalkyl C 1-6 alkyl group wherein each group described in the substituent group e-2 has one to three substituents selected from the following substituent group f: [Substituent group f] halogen atom, hydroxyl group, cyano group, amino group, nitro group, C 3-8 cycloalkyl group, C 1 -6-alkoxy, C6-10-aryloxy, 5-10-membered heterocyclic oxy, C1-6-alkoxycarbonyl, C1-6-alkylsulfonyl, mono-C6-10-arylamino, trifluoromethyl, trifluoromethoxy and C1-6-alkyl. Agrochemical composition according to one of the claims 1 to 3, wherein in the formula (I) E is a furyl group, thienyl group, Pyrrolyl group or phenyl group (where E is optionally may have a substituent selected from following substituent group g-1 and substituent group g-2): [substituent g-1] C 3-8 -cycloalkyl-C 1-6 -alkyl, phenyl-C 1-6 -alkyl, Furyl C1-6 alkyl, thienyl C1-6 alkyl, benzofuryl C1-6 alkyl, Benzothienyl-C 1-6 -alkyl, C 1-6 -alkoxy, phenoxy, C 3-8 -cycloalkyl-C 1-6 -alkoxy, Phenyl-C 1-6 -alkoxy, furyl-C 1-6 -alkoxy, thienyl-C 1-6 -alkoxy, Pyridyl C 1-6 alkoxy, phenoxy C 1-6 alkyl, and pyridyloxy C 1-6 alkyl; and [Substituent group g-2] C 3-8 cycloalkyl-C 1-6 alkyl, Phenyl-C1-6-alkyl, furyl-C1-6-alkyl, thienyl-C1-6-alkyl, Benzofuryl-C 1-6 -alkyl, benzothienyl-C 1-6 -alkyl, C 1-6 -alkoxy, Phenoxy group, C 3-8 -cycloalkyl-C 1-6 -alkoxy, phenyl-C 1-6 -alkoxy, Furyl C 1-6 alkoxy, thienyl C 1-6 alkoxy, pyridyl C 1-6 alkoxy, phenoxy C 1-6 alkyl and pyridyloxy-C 1-6 alkyl group; wherein each in the substituent group g-2 group has one to three substituents selected from the following substituent group h: [substituent H] Halogen atom, hydroxyl group, cyano group and C 1-6 -alkyl radical. Agrochemical composition according to one of the claims 1 to 3, wherein in the formula (I) E is a 2-furyl group, 2-thienyl group, 3-pyrrolyl group or phenyl group (where E is optionally may have a substituent selected from Substituent group g-1 and substituent group g-2). An agrochemical composition according to claim 1, wherein in formula (I) X represents a radical of the formula [-C (= O) -NH-CH ₂ -] and E represents a 2-furyl group, 2-thienyl group, 3-pyrrolyl group or phenyl group (wherein E may optionally have a substituent selected from substituent group g-1 or substituent group g-2). Agrochemical composition according to one of the claims 1 to 8, wherein the phytopathogenic microbes are plant pathogens Filamentous fungi, except Aspergillus, are. Method of control or prevention of plant diseases caused by plant pathogenic microbes, except Aspergillus, comprising applying an effective Amount of agrochemical composition according to one of the claims 1 to 8 on useful crops. The method of claim 10, wherein the composition applied by foliar application, soil treatment or seed disinfection becomes. Use of the compound of the formula (I) or a Salt thereof or a hydrate thereof according to claim 1 for the preparation an agrochemical composition.