WO2020054531A1 - Plant disease control agent - Google Patents

Abstract

The present invention provides a plant disease control agent which contains a compound represented by formula (1). (In the formula, each of X¹ and X⁴ represents a fluorine atom, a chlorine atom or the like; each of X² and X³ represents a hydrogen atom or the like; X^a represents a group expressed by formula (2) or (3); each of Ja and Jb represents an oxygen atom or the like; G represents an optionally substituted phenyl group or the like; Aa represents an optionally substituted alkyl group, a phenyl group or the like; Q represents an oxygen atom or the like; and Ab represents a heterocyclic group which may be substituted by a halogen atom or the like.)

Description

Plant disease control agent

The present invention relates to a plant disease controlling agent. More specifically, the present invention relates to a plant disease controlling agent, a novel compound and a plant disease controlling method.
Priority is claimed on Japanese Patent Application No. 2018-173443 filed on September 14, 2018, the content of which is incorporated herein by reference.

Plants have acquired physical and chemical resistance mechanisms during the course of evolution against attacks by external pathogens. The physical resistance mechanism is, for example, a coating material such as a wax layer or a cuticle layer, or a cell wall, which serves as a barrier for the entry of pathogenic bacteria. On the other hand, the chemical resistance mechanism is a system that inhibits the growth of pathogenic bacteria, and includes, for example, resistance factors accumulated innately in plants and resistance factors inducibly biosynthesized and accumulated. Can be

In recent years, in order to protect plants from disease stress, attempts have been made to activate chemical resistance mechanisms by externally administering drugs to improve plant resistance. Such an agent can be called a resistance inducer, and various inducers have been studied so far. For example, it has been clarified that treatment of tobacco with salicylic acid or acetylsalicylic acid induces resistance to tobacco mosaic virus (TMV) (see Non-Patent Document 1).

誘導 Inducing plant resistance and protecting plants from infection with plant pathogens in this way is very useful in growing healthy plants and securing food.

It is disclosed that chlorine-substituted pyridine compounds have a plant disease control effect (Patent Documents 1 to 7). However, it is known that the above compounds may cause phytotoxicity and may have a weak plant disease control effect. As for the fluorine-substituted pyridine compound, similar plant disease controlling agents are disclosed (Patent Documents 8 to 12), but there is no specific description about the plant disease controlling agent of the present invention.

JP-A-62-277361 JP-A-63-93766 JP-A-1-283270 JP-A-9-165374 JP-A-10-95772 JP-A-11-171864 International Publication No. 2005-68430 WO 2008/098928 International Publication No. 96-03047 JP-A-1-272569 International Publication No. 2009-11305 International Publication No. 2014-124988

An object of the present invention is to provide a plant disease controlling agent, a novel compound and a plant disease controlling method with reduced phytotoxicity.

The present invention includes the following aspects.
[1] A compound represented by the following formula (1).

In the formula (1), X ¹ and X ⁴ may be the same or different and represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, and ^one of X ¹ and X ⁴ is Represents a fluorine atom, a chlorine atom or a trifluoromethyl group, X ² and X ³ may be the same or different, and are a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group,
X ^a is ^{a group} represented by the following formula (2) or (3);

In the formula (2), Ja and Jb may be the same or different and represent an oxygen atom or a sulfur atom;
G is
An alkyl group having 1 to 12 carbon atoms which may be substituted with 1 to 3 groups selected from the group consisting of the following group C group, thiol group, methoxycarbonyl group and N-tert-butoxycarbonylamino group;
An alkenyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
An alkynyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C,
An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
An alkylsulfonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of group C,
A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of group D below, a benzyl group, a phenyl group and a phenoxy group;
A phenylsulfonyl group optionally substituted with 1 to 4 groups selected from the following group D groups:
A phenyl group which may be substituted with 1 to 5 groups selected from the group consisting of the following group D, a phenoxy group and a benzyl group;
5,6,7,8-tetrahydronaphthyl group,
A naphthyl group or a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D below;
Wherein X ¹ and X ⁴ are both chlorine atoms, X ² and X ³ are both hydrogen atoms, and Aa is 1 to 5 members selected from the group consisting of the following group D, phenoxy and benzyl G may be a hydrogen atom when it is a phenyl group which may be substituted with a group or a heterocyclic group which may be substituted with 1 to 4 groups selected from groups in the following group D;
Aa is
An alkyl group having 1 to 12 carbon atoms which may be substituted with 1 to 3 groups selected from the group consisting of the following group C group, thiol group, methoxycarbonyl group and N-tert-butoxycarbonylamino group;
An alkenyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
An alkynyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
A phenyl group which may be substituted with 1 to 5 groups selected from the group consisting of the following group D, a phenoxy group and a benzyl group;
5,6,7,8-tetrahydronaphthyl group,
Naphthyl group,
An alkenyloxy group having 2 to 4 carbon atoms,
A phenyloxy group, or
A heterocyclic group which may be substituted with 1 to 4 groups selected from the following group D;
Provided that Aa is an alkyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C, or a group consisting of the following group D, phenoxy group and benzyl group When a phenyl group which may be substituted with 1 to 4 groups selected from the following is selected, G is not a methyl group,
When X ¹ is a chlorine atom, X ² , X ³ and X ⁴ are hydrogen atoms, Ja and Jb are simultaneously oxygen atoms, and G is an alkyl group having 1 to 4 carbon atoms, Aa is as follows: Not an alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 groups selected from the group C group,
In the formula (3), Q represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH— or a divalent group represented by the formula: —N (CH ₃ ) —,
Ab is
A phenyl group optionally substituted with 1 to 4 groups selected from the following group D groups, or a heterocyclic group optionally substituted with 1 to 4 groups selected from the following group D groups: Shows,
When X ¹ and X ⁴ are chlorine atoms, X ² and X ³ are hydrogen atoms, and Q is an oxygen atom, Ab represents an amino group, a trifluoromethyl group, a trifluoromethoxy group, an acetoxy group, a nitro group. A phenyl group substituted by only one group selected from the group consisting of a group and a cyano group; a phenyl group substituted by only one or two halogen atoms; a 2-thienyl group; a 3-furanyl group; Does not represent a 4-yl group; a 2-methylpyridin-3-yl group; or a 2-cyanopyridin-3-yl group;
The heterocyclic group represents a group selected from the following group E,
The group C includes one to three groups selected from a halogen atom, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, and a group of the following group D. A pyridyl group which may be substituted with a phenyl group which may be substituted with 1 to 4 groups selected from the following group D;
Group D includes a halogen atom, a hydroxyl group, an amino group, a methylthio group, an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, and 1 to 3 halogen atoms. Alkyloxy group having 1 to 4 carbon atoms, alkylcarbonyl group having 1 to 4 carbon atoms, methoxycarbonyl group, ethoxycarbonyl group, benzylaminocarbonyl group, acetoxy group, nitro group, cyano group, phenyl group, phenylcarbonyl Group and dimethylamino group,
Group E includes pyridyl, thiazolyl, pyrazinyl, pyridazinyl, isoxazolyl, pyrimidinyl, benzimidazolyl, thienyl, furanyl, benzoxanyl, 2,3-dihydrobenzo [b] [1,4]. A dioxin-6-yl group, a dihydrothiazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a (1,1-dioxobenzo [d] isothiazol-3-yl) oxy group, a dibenzofuranyl group, an isothiazolyl group, and A group consisting of triazolyl groups.
[2] The compound according to [1], wherein in the formula (1), X ¹ , X ² , X ³ and X ⁴ are a hydrogen atom, a fluorine atom or a chlorine atom.
[3] The compound according to [1], wherein in the formula (1), X ¹ and X ⁴ are the same and each represent a fluorine atom or a chlorine atom, and X ² and X ³ are hydrogen atoms.
[4] In the formula (1), ^{X a} is a group represented by the formula (2), according to any one of in the formula (2), Ja is an oxygen atom [1] to [3] Compound.
[5] In any of [1] to [3], in the formula (1), ^Xa is a group represented by the formula (3), and in the formula (3), Q is an oxygen atom. A compound as described.
[6] The compound according to [5], wherein in the formula (3), Ab is a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D group.
[7] A plant disease controlling agent comprising as an active ingredient at least one of the compounds according to any of [1] to [6].
[8] The compound according to any one of [1] to [6] or the plant disease controlling agent according to [7], a foliar part of a plant, soil, paddy water for growing rice, a carrier for growing a plant, A method for controlling plant diseases by treating hydroponic water (which may contain nutrients), plant roots, rhizomes, tubers, bulbs, germinated plants or seeds.

According to the present invention, it is possible to provide a novel compound with reduced phytotoxicity, a plant disease controlling agent containing the compound as an active ingredient, and a plant disease controlling method using the same. The plant disease controlling agent and the novel compound of the present invention have excellent resistance-inducing activity and are useful for controlling plant diseases.

In one embodiment, the present invention provides a compound represented by the following formula (1). In one embodiment, the present invention provides a plant disease controlling agent containing the compound as an active ingredient.

In the formula (1), X ¹ and X ⁴ may be the same or different and represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, and ^one of X ¹ and X ⁴ is X ² and X ³ may be the same or different and represent a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group.

In the formula (1), X ¹ , X ² , X ³ and X ⁴ are preferably a hydrogen atom, a fluorine atom or a chlorine atom.
In the formula (1), X ¹ and X ⁴ are preferably a fluorine atom or a chlorine atom, and X ² and X ³ are preferably a hydrogen atom.
In the formula (1), X ¹ and X ⁴ are the same and are preferably a fluorine atom or a chlorine atom, and X ² and X ³ are preferably a hydrogen atom.

In the formula (1), ^Xa is ^{a group} represented by the following formula (2) or (3).

中 In the formula (2), Ja and Jb may be the same or different and represent an oxygen atom or a sulfur atom.

In the formula (2), G represents a carbon atom which may be substituted with 1 to 3 groups selected from the group consisting of the following group C group, thiol group, methoxycarbonyl group and N-tert-butoxycarbonylamino group. An alkyl group of the formulas 1 to 12, an alkenyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following group C, and 1 to 3 selected from the following group C An alkynyl group having 2 to 8 carbon atoms which may be substituted by a group represented by the following: an alkylcarbonyl group having 1 to 8 carbon atoms optionally substituted by 1 to 3 groups selected from the following group C: An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the group C group, and which may be substituted with 1 to 3 groups selected from the following group C groups Good alkylsulfonyl group having 1 to 8 carbon atoms, group D shown below, benzyl A phenylcarbonyl group optionally substituted with 1 to 4 groups selected from the group consisting of phenyl group and phenoxy group, and a phenylcarbonyl group optionally substituted with 1 to 4 groups selected from the following group D Phenylsulfonyl group, phenyl group optionally substituted with 1 to 5 groups selected from the group consisting of the following group D, phenoxy group and benzyl group, 5,6,7,8-tetrahydronaphthyl group, naphthyl Or a group represented by a heterocyclic group which may be substituted with 1 to 4 groups selected from the following group D (where the heterocyclic group is a group selected from the following group E): It is. Among these, G is preferably a phenyl group which may be substituted with 1 to 5 groups selected from the following group D groups.

In the formula (2), Aa is a carbon atom which may be substituted with 1 to 3 groups selected from the group consisting of the following group C group, thiol group, methoxycarbonyl group and N-tert-butoxycarbonylamino group. An alkyl group of the formulas 1 to 12, an alkenyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following group C, and 1 to 3 selected from the following group C An alkynyl group having 2 to 8 carbon atoms which may be substituted by a group represented by the following: an alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 groups selected from the following group C; A phenyl group, a 5,6,7,8-tetrahydronaphthyl group, a naphthyl group, a carbon number of 2 which may be substituted with 1 to 5 groups selected from the group consisting of group D, phenoxy group and benzyl group; ~ 4 alkenyloxy and phenyloxy groups Or a group represented by a heterocyclic group which may be substituted with 1 to 4 groups selected from the following group D (here, the heterocyclic group is a group selected from the following group E). . Provided that Aa is an alkyl group having 1 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following group C, or a group consisting of the following group D, phenoxy group and benzyl group When G represents a phenyl group which may be substituted with one to four groups selected from G, G is not a methyl group. When X ¹ is a chlorine atom, X ² , X ³ and X ⁴ are hydrogen atoms, Ja and Jb are simultaneously oxygen atoms, and G is an alkyl group having 1 to 4 carbon atoms, Aa is And an alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C groups. X ¹ and X ⁴ are both chlorine atoms; X ² and X ³ are both hydrogen atoms; and Aa is 1 to 5 selected from the group consisting of group D below, phenoxy group and benzyl group. Phenyl group which may be substituted with 1 to 4 groups, or heterocyclic group which may be substituted with 1 to 4 groups selected from the following group D (where the heterocyclic group is G) may be a hydrogen atom.
Among these, Aa is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, and 1 to 5 groups selected from the following group D groups. It is preferably a phenyl group which may be substituted, or a heterocyclic group which may be substituted by 1 to 4 groups selected from the following group D, and an alkyl group having 1 to 12 carbon atoms, An alkenyl group having 2 to 8 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, a phenyl group which may be substituted with 1 to 5 groups selected from the following group D, or 1 selected from the following group D More preferably, it is a heterocyclic group which may be substituted with up to 4 groups.

In the formula (3), Q represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH—, or a divalent group represented by the formula: —N (CH ₃ ) —. Among these, Q is preferably an oxygen atom.

In the formula (3), Ab represents a phenyl group which may be substituted with 1 to 4 groups selected from the following group D (provided that X ¹ and X ⁴ are chlorine atoms, X ² and X ^{2 When 3} is a hydrogen atom and Q is an oxygen atom, Ab is one selected from the group consisting of "amino group, trifluoromethyl group, trifluoromethoxy group, acetoxy group, nitro group and cyano group" Does not represent a phenyl group substituted only with a group or a phenyl group substituted only with 1 to 2 halogen atoms.) Or 1 to 4 groups selected from the group D below. Wherein the heterocyclic group is a group selected from the following group E, provided that X ¹ and X ⁴ are chlorine atoms, X ² and X ³ are hydrogen atoms, and Q When is an oxygen atom, Ab is a 2-thienyl group, 3-furanyl Shows a pyridin-4-yl group, shows no 2-methyl-pyridin-3-yl group or a 2-cyano-3-yl group.).
Among these, Ab is preferably a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D groups, and may be substituted with 1 to 2 halogen atoms. More preferably, it is a heterocyclic group (preferably a pyridyl group or an isothiazolyl group).

Group C is one to three groups selected from a halogen atom, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, and a group of the following Group D. The group includes a pyridyl group which may be substituted, and a phenyl group which may be substituted with 1 to 4 groups selected from the following group D groups.

Group D includes a halogen atom, a hydroxyl group, an amino group, a methylthio group, an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, and 1 to 3 halogen atoms. C1-4 alkyloxy group, C1-4 alkylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, benzylaminocarbonyl group, acetoxy group, nitro group, cyano group, phenyl group, phenylcarbonyl group And dimethylamino groups. Among these, group D includes a halogen atom, a hydroxyl group, an amino group, an alkyl group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, an alkyloxy group having 1 to 4 carbon atoms, nitro group, It is preferably a group consisting of a group, a cyano group, and a dimethylamino group, and more preferably a group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms, and a cyano group.

Group E includes pyridyl, thiazolyl, pyrazinyl, pyridazinyl, isoxazolyl, pyrimidinyl, benzimidazolyl, thienyl, furanyl, benzoxanyl, 2,3-dihydrobenzo [b] [1,4] dioxin -6-yl group, dihydrothiazolyl group, benzothiazolyl group, benzoisothiazolyl group, (1,1-dioxobenzo [d] isothiazol-3-yl) oxy group, dibenzofuranyl group, isothiazolyl group, and triazolyl It is a group consisting of groups. Among these, the group E is preferably a group consisting of a pyridyl group and an isothiazolyl group.

に お い て In this embodiment, the alkyl group having 1 to 12 carbon atoms means a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-octyl group, and a cycloalkyl group. A propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc., preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a cyclohexyl group, a n-propyl group; An octyl group;

ア ル ケ ニ The alkenyl group having 2 to 8 carbon atoms means a linear, branched or cyclic alkenyl group having one or more double bonds at any position of the alkyl group having 2 to 8 carbon atoms. Examples of the alkenyl group having 2 to 8 carbon atoms include ethenyl, 1-propenyl, 2-propenyl, 2-butenyl, isopropenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, Examples thereof include a 1-cyclohexenyl group, and a 2-propenyl group is preferable.

ア ル The alkynyl group having 2 to 8 carbon atoms means a linear, branched or cyclic alkynyl group having one or more triple bonds at any position of the alkyl group having 2 to 8 carbon atoms. Examples of the alkynyl group having 2 to 8 carbon atoms include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 3-butynyl group, a cyclopropylethynyl group, and a 2-propynyl group is preferable.

ア ル キ ル The alkyloxy group having 1 to 4 carbon atoms means a group consisting of an oxygen atom substituted with a linear, branched or cyclic alkyl group having 1 to 4 carbon atoms. Examples of the alkyloxy group having 1 to 4 carbon atoms include methoxy, ethoxy, n-propoxy, isopropyloxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, and cyclopropyloxy. Group, cyclobutyloxy group and the like, and preferably a methoxy group.

ア ル キ ル The alkyl group having 1 to 8 carbon atoms means a carbonyl group substituted with a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms. Examples of the alkylcarbonyl group having 1 to 8 carbon atoms include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, an isopropylcarbonyl group, an n-butylcarbonyl group, a sec-butylcarbonyl group, an isobutylcarbonyl group, a tert- Examples include a butylcarbonyl group, an n-octylcarbonyl group, a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, a cyclohexylcarbonyl group, and the like.

ア ル キ ル The alkylsulfonyl group having 1 to 8 carbon atoms means a sulfonyl group substituted with a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms. Examples of the alkylsulfonyl group having 1 to 8 carbon atoms include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, isobutylsulfonyl, tert- Examples include a butylsulfonyl group, an n-octylsulfonyl group, a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group, and a cyclohexylsulfonyl group.

Examples of the 5,6,7,8-tetrahydronaphthyl group include a 5,6,7,8-tetrahydronaphthalen-1-yl group and a 5,6,7,8-tetrahydronaphthalen-2-yl group. .

A halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

ア ル ケ ニ An alkenyloxy group having 2 to 4 carbon atoms means a group consisting of an oxygen atom substituted with an alkenyl group having 2 to 4 carbon atoms. Examples of the alkenyloxy group having 2 to 4 carbon atoms include a vinyloxy group, a 1-propenyloxy group, a 2-propenyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, and a 3-butenyloxy group. , A vinyloxy group.

に お い て In the present specification, unless otherwise specified, the symbol “-” for bonding atoms and / or groups in the structural formula represents a single bond, and “=” represents a double bond. For example, in the formula (2), all symbols “−” indicate a single bond, and all symbols “=” indicate a double bond.

In Group D, the alkyl group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms includes, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec- -Butyl group, isobutyl group, tert-butyl group, trifluoromethyl group, chloromethyl group and the like.

In Group D, the alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy Group, sec-butyloxy group, isobutyloxy group, tert-butyloxy group, trifluoromethyloxy group, chloromethyloxy group and the like.

In the formula (2), a more preferred embodiment of Aa is an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the group C group; An alkenyl group having 2 to 3 carbon atoms which may be substituted by 1 to 3 groups; an alkynyl group having 2 to 3 carbon atoms which may be substituted by 1 to 3 groups selected from groups in Group C; A phenyl group which may be substituted with 1 to 3 groups selected from a group D group and a phenoxy group; a heterocyclic group which may be substituted with 1 to 4 groups selected from a group D group; An alkyloxy group having 1 to 4 carbon atoms, which may be substituted with 1 to 3 groups selected from the group C group; an alkenyloxy group having 2 to 4 carbon atoms; or a phenyloxy group.

In the formula (2), an even more preferred embodiment of Aa is an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 3 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, a phenyl group, or a halogen atom. A phenyl group, a phenyl group substituted by an alkyl group having 1 to 4 carbon atoms which may be substituted by a halogen atom, a phenyl group substituted by an alkyloxy group having 1 to 4 carbon atoms, and a phenyl substituted by a hydroxyl group Group, phenyl group substituted by amino group, phenyl group substituted by nitro group, phenyl group substituted by halogen atom and nitro group, phenyl group substituted by dimethylamino group, alkenyloxy having 2 to 4 carbon atoms A phenyloxy group or a heterocyclic group (preferably a pyridyl group or an isothiazolyl group) which may be substituted with a halogen atom. Still more preferred embodiments include an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 3 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, a phenyl group, a phenyl group substituted by a halogen atom, and a halogen atom. A group represented by a substituted phenyl group substituted by a substituted alkyl group having 1 to 4 carbon atoms or a heterocyclic group (preferably a pyridyl group or an isothiazolyl group) optionally substituted by a halogen atom.

In the formula (2), G is more preferably a phenyl group, a phenyl group substituted with a halogen atom, a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom, A phenyl group substituted with an alkyloxy group of the formulas 1 to 4, a phenyl group substituted with a cyano group, or a hydrogen atom (provided that when G is a hydrogen atom, X ¹ and X ⁴ are both chlorine atoms; X ² and X ³ are both hydrogen atoms, Ja and Jb are both oxygen atoms, and Aa is a phenyl group or an alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom. A substituted phenyl group, a phenyl group substituted with an alkyloxy group having 1 to 4 carbon atoms, a phenyl group substituted with a halogen atom, a phenyl group substituted with a hydroxyl group, and a phenyl group substituted with an amino group. A phenyl group substituted with a nitro group, a phenyl group substituted with a halogen atom and a nitro group, a phenyl group substituted with a dimethylamino group, or a heterocyclic group optionally substituted with a halogen atom (more preferably Is a pyridyl group or an isothiazolyl group), and still more preferred embodiments include a phenyl group, a phenyl group substituted with a halogen atom, a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms, and a cyano group. Or a hydrogen atom (provided that when G is a hydrogen atom, X ¹ and X ⁴ are both chlorine atoms, X ² and X ³ are both hydrogen atoms, and Ja and Jb is an oxygen atom, and Aa is a phenyl group, a phenyl group substituted with a halogen atom, or a heterocyclic group optionally substituted with a halogen atom ( And more preferably a pyridyl group or an isothiazolyl group).

に お い て In the formula (2), a more preferred embodiment of Ja is an oxygen atom.

化合物 The compound represented by the formula (1) may exist as a hydrate or any solvate, and these hydrates or solvates are also included in the present embodiment. Further, the compound represented by the formula (1) may have an asymmetric carbon, but the asymmetric carbon may have an arbitrary configuration. Pure stereoisomers such as optical isomers or diastereoisomers based on these asymmetric carbons, mixtures of arbitrary stereoisomers, and racemates are all included in the present embodiment. Further, the compound represented by the formula (1) may have one or more double bonds, and may also have a geometric isomer derived from a double bond or a ring structure. It goes without saying that any geometric isomer or a mixture of any geometric isomers in pure form is also encompassed in this embodiment.

Next, a method for producing the compound of the present embodiment will be described. The compound of the present embodiment is produced, for example, according to the following methods A to G, but the production method of the compound of the present embodiment is not limited thereto.

[Method A]

Among the compounds represented by the formula (1), the compound represented by the formula (2 ′) is a compound of the formula (51) (in the formula (51), X ¹ , X ² , X ³ and X ⁴ are represented by the formula (1) )) And a compound of formula (52) (wherein, G is the same as defined in formula (2)) of formula (52) (compound of formula (52) In 53), X ¹ , X ² , X ³ and X ⁴ are the same as defined in formula (1).) And a compound of formula (54) (in formula (54), Aa is represented by formula (2) And Jb represents an oxygen atom or a sulfur atom.).

First, in the first step, a compound of the formula (53) is produced by reacting a compound of the formula (51) with a compound of the formula (52) in the presence or absence of a base in the presence of a condensing agent.

化合物 As the starting material, the compound represented by the formula (51), a commercially available reagent may be used, or a synthesized compound may be used. The compound represented by the formula (51) is described, for example, in JP-A-63-93766, JP-A-1-283270, R.A. E. FIG. Banks, et al. Heterocyclic @ polyfluoro-compounds. Part XII. Synthesis and some reactions and of 2,3,5,6-tetrafluoro-4-iodopyridine, J. Mol. Chem. Soc. (C), 2091-2095 (1967).

溶媒 Solvents used in the reaction include, for example, dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.

縮合 Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.

塩 基 Examples of the base used in the reaction include 4-dimethylaminopyridine. The amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).

使用 The amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).

使用 The amount of the compound represented by the formula (52) is in the range of 1 to 5 equivalents based on the compound represented by the formula (51).

The reaction temperature is selected, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C. The reaction time ranges, for example, from 10 minutes to 24 hours, preferably from 30 minutes to 4 hours.

Next, in the second step, the compound represented by the formula (2 ') can be produced by reacting the compound of the formula (53) with the compound of the formula (54) in the presence of a base.

Examples of the solvent used in the reaction include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.

塩 基 The base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base to be used is in the range of 1 to 10 equivalents based on the compound of the formula (53).

使用 The amount of the compound represented by the formula (54) is in the range of 1 to 5 equivalents based on the compound represented by the formula (53).

The reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of 10 to 80 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

[Method B]

Among the compounds represented by the formula (1), the compound represented by the formula (2 ′) is a compound represented by the formula (53) and a compound represented by the formula (55) (wherein Aa is the definition in the formula (2) And Jb represents an oxygen atom or a sulfur atom.).

That is, the compound represented by the formula (2 ') can be produced by reacting the compound of the formula (53) with the compound of the formula (55) in the presence of a base.

Examples of the solvent used in the reaction include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.

塩 基 The base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base to be used is in the range of 0.01 to 10 equivalents based on the compound of the formula (53).

使用 The amount of the compound represented by the formula (55) is in the range of 1 to 5 equivalents based on the compound represented by the formula (53).

The reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of -10 to 80 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

[Method C]

Among the compounds represented by the formula (1), the compound represented by the formula (2 ′) is a compound of the formula (51) (in the formula (51), X ¹ , X ² , X ³ and X ⁴ are represented by the formula (1) )) To the compound of formula (56) (wherein X ¹ , X ² , X ³ and X ⁴ are the same as defined in formula (1)). It can also be manufactured by the following method.

First, in the first step, the compound of the formula (56) is produced by chlorinating the compound of the formula (51).

溶媒 As the solvent used for the reaction, for example, tetrahydrofuran, toluene, ethyl acetate, dichloromethane, chloroform, acetonitrile and the like can be mentioned, but the reaction can also be carried out without a solvent.

塩 素 Examples of the chlorinating agent used in the reaction include thionyl chloride, oxalyl chloride and the like. The amount of the chlorinating agent to be used is in the range of 1 to 5 equivalents based on the compound of the formula (51).

The reaction temperature is, for example, in the range of −20 to 100 ° C., and preferably in the range of 10 to 80 ° C. Reaction times range from 10 minutes to 24 hours, preferably from 30 minutes to 4 hours.

Next, in the second step, the compound of the formula (56) and the compound of the formula (57) (in the formula (57), Aa and G are the same as defined in the formula (2), and Jb is an oxygen atom or a sulfur atom. (Indicating an atom)) in the presence of a base to produce a compound represented by the formula (2 ′).

Examples of the solvent used in the reaction include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.

塩 基 The base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base used is in the range of 1 to 10 equivalents based on the compound of the formula (57).

使用 The amount of the compound represented by the formula (57) is in the range of 1 to 5 equivalents based on the compound represented by the formula (56).

The reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of 10 to 80 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

[Method D]

Among the compounds represented by the formula (1), the compound represented by the formula (2 ′) is a compound of the formula (51) (in the formula (51), X ¹ , X ² , X ³ and X ⁴ are represented by the formula (1) )), Can also be produced by the following method via the compound of the formula (59).

First, in the first step, the compound of the formula (51) and the compound of the formula (58) (in the formula (58), Aa has the same definition as in the formula (2), and Jb represents an oxygen atom or a sulfur atom. Is reacted in the presence or absence of a base in the presence of a condensing agent to produce a compound of the formula (59).

溶媒 Solvents used in the reaction include, for example, dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.

縮合 Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.

塩 基 Examples of the base used in the reaction include 4-dimethylaminopyridine. The amount of the base used is in the range of 0.01 to 1.2 equivalents based on the carboxylic acid (51).

使用 The amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51).

使用 The amount of the compound represented by the formula (58) is in the range of 1 to 5 equivalents based on the compound represented by the formula (51).

The reaction temperature is selected, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C. The reaction time ranges, for example, from 10 minutes to 24 hours, preferably from 30 minutes to 4 hours.

Next, in the second step, the compound of the formula (59) and the compound of the formula (60) (in the formula (60), G is the same as the definition in the formula (2), Z is an iodine atom, a bromine atom, A leaving group such as a chlorine atom, a p-toluenesulfonyl group, a methanesulfonyl group, etc.) in the presence of a base to produce a compound represented by the formula (2 ′).

Examples of the solvent used in the reaction include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.

塩 基 The base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base to be used is in the range of 1 to 10 equivalents based on the compound of the formula (59).

使用 The amount of the compound represented by the formula (60) is in the range of 1 to 5 equivalents based on the compound represented by the formula (59).

The reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of 10 to 80 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

[Method E]

Among the compounds represented by the formula (1), the compound represented by the formula (2 ′) is a compound represented by the formula (56) (in the formula (56), X ¹ , X ² , X ³ and X ⁴ are represented by the formula (1) )), Can also be produced by the following method via the compound of the formula (59).

First, in the first step, the compound of the formula (59) is produced by reacting the compound of the formula (56) with the compound of the formula (58) in the presence of a base.

Examples of the solvent used in the reaction include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.

塩 基 The base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base to be used is in the range of 1 to 10 equivalents based on the compound of the formula (56).

使用 The amount of the compound represented by the formula (58) is in the range of 1 to 5 equivalents based on the compound represented by the formula (56).

The reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of 10 to 80 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

Next, in the second step, the compound of the formula (2 ′) can be produced by reacting the compound of the formula (59) with the compound of the formula (60) in the same manner as in the above-mentioned Method D.

[Method F]

Among the compounds represented by the formula (1), the compound represented by the formula (3 ′) is a compound represented by the formula (51) (in the formula (51), X ¹ , X ² , X ³ and X ⁴ are represented by the formula From the definition in (1), the compound represented by the formula (61) (in the formula (61), X ¹ , X ² , X ³ and X ⁴ have the same definition as in the formula (1)). ) Can be produced by the following method.

First, in the first step, the compound represented by the formula (61) is produced by reducing the compound represented by the formula (51).

溶媒 The solvent used for the reaction includes, for example, tetrahydrofuran, dimethoxyethane, 1,4-dioxane, dichloromethane, chloroform, toluene and the like.

還 元 Examples of the reducing agent used in the reaction include a borane-tetrahydrofuran complex and a borane-dimethylsulfide complex. The amount of the reducing agent to be used is in the range of 3 to 6 equivalents based on the compound represented by the formula (51).

The reaction temperature is in the range of −20 to 100 ° C., preferably 20 to 80 ° C. The reaction time ranges from 10 minutes to 8 hours, preferably from 30 minutes to 6 hours.

Next, in the second step, the compound of the formula (61) and the compound of the formula (62) (in the formula (62), Ab is the same as the definition in the formula (3)) are present in the presence or absence of a base. The compound of the formula (3 ') is produced by reacting in the presence of a condensing agent.

溶媒 Solvents used in the reaction include, for example, dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.

縮合 Examples of the condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 1,3-dicyclohexylcarbodiimide and the like.

塩 基 Examples of the base used in the reaction include 4-dimethylaminopyridine. The amount of the base to be used is in the range of 0.01 to 1.2 equivalents based on the compound represented by the formula (61).

使用 The amount of the condensing agent used is in the range of 1.0 to 1.2 equivalents based on the compound represented by the formula (61).

使用 The amount of the compound represented by the formula (62) is in the range of 1 to 5 equivalents based on the compound represented by the formula (61).

The reaction temperature is selected, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C. The reaction time ranges, for example, from 10 minutes to 24 hours, preferably from 30 minutes to 4 hours.

[Method G]

Among the compounds represented by the formula (1), the compound represented by the formula (3 ′) is a compound represented by the formula (61) (in the formula (61), X ¹ , X ² , X ³ and X ⁴ are represented by the formula It is also produced by reacting the same as defined in (1)) with a compound of the formula (63) (where Ab is the same as defined in the formula (3)). You.

That is, the compound of the formula (3 ') is produced by reacting the compound of the formula (61) with the compound of the formula (63) in the presence of a base.

Examples of the solvent used in the reaction include tetrahydrofuran, 1,4-dioxane, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, 1,2-dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like. Of mixed solvents.

塩 基 The base used for the reaction includes sodium hydride, n-butyllithium, triethylamine, N, N-diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium carbonate, potassium carbonate and the like. The amount of the base to be used is in the range of 1 to 10 equivalents based on the compound of the formula (61).

使用 The amount of the compound represented by the formula (63) is in the range of 1 to 5 equivalents based on the compound represented by the formula (61).

The reaction temperature is, for example, in the range of -78 to 190 ° C, preferably in the range of 10 to 80 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

Specific embodiments of the compound represented by the formula (2 ″) among the compounds represented by the formula (1) are shown in Tables 1 to 6 below. As a specific compound represented by the formula (2 ″), X ¹ , X ² , X ³ , X ⁴ , Ja and Jb are combinations of the substituents shown in the following Tables 1 and 2, and Aa is Compounds in which Tables 3 to 4 and G are combinations of the substituents shown in Tables 5 and 6 are mentioned.

Hereinafter, the following abbreviations may be used in this specification.
n: Normal sec: Secondary tert: Tertiary

の う ち Specific embodiments of the compound represented by the formula (3 ′) among the compounds represented by the formula (1) are shown in Tables 7 and 8 below.

As a specific compound represented by the formula (3 ′), X ¹ , X ² , X ³ , X ⁴ and Q are combinations of the substituents shown in the following Tables 7 to 8, and Ab is a pyridyl group Thiazolyl group, pyrazinyl group, pyridazinyl group, isoxazolyl group, pyrimidinyl group, benzimidazolyl group, thienyl group, furanyl group, benzoxanyl group, 2,3-dihydrobenzo [b] [1,4] dioxin-6-yl group, Dihydrothiazolyl, benzothiazolyl, benzoisothiazolyl, (1,1-dioxobenzo [d] isothiazol-3-yl) oxy, dibenzofuranyl, isothiazolyl, triazolyl, 2,6-dichloro A compound consisting of a -4-pyridyl group, a 2,6-difluoro-4-pyridyl group or a 3,4-dichloro-5-isothiazolyl group And the like.

[Plant pathogen]
The plant pathogen to be controlled by the plant disease controlling agent of the present embodiment is not particularly limited, but includes fungi, bacteria, viruses, and the like.

Examples of phytopathogenic fungi include Pythium ultimum, vegetable wilt fungus (Rhizoctonia solani), cucurbit ripening fungus (Fusarium oxysporum), vegetable wilt fungus (Fusarium xorum) Homopsis root rot fungus (Phomopsis sclerotioides), cruciferous vegetable root club fungus (Plasmodiophora brassicae), potato powdery scab (Spongospora suberanea sclera) , Soybean white rot fungus (Sclerotium @ rolfsiii), tomato brown Rot rot fungus (Pyrenochaeta lycopersici), wheat streak disease (Cephalosporium gramineum), soybean rot fungus (Phialophora gregata), soybean scab fungus (Phytophthora seroic rot) Typhula incarnata, snow rot black sclerotium sclerotium (Typhula ischariensis), sugar beet seedling wilt fungus (Aphanomyces cochlioides), tobacco black rot fungus (Thielaviopsis basicola), wheat germinaceae germinaceae sclerotiomycium spores ternaria @ alternata, pear black spot fungus (Alternaria @ kikutiana), gray mold fungus (Botrytis @ cinerea), rice sesame leaf blight fungus (Cochliobolus @ miyabeanus), and potato anthracnose fungus (Cololium glaucoma) Disease pathogens (Colletotrichum lagenarium), tomato wilt fungus (Fusarium ｙoxysporum f. Sp. Ｃｏlycopersici), rice blight seedlings (Gibberella fujikuroi), grape downy mildew (Plasvia spelling grape spores and grape sprouts) lomerella ingulata, rice blast fungus (Pyricularia oryzae), rice seedling wilt (Pythium graminicola), tomato sclerotium bacillus (Sclerotinia ｏｒ minor), potato half-blight wilt fungus (Verticillium bacillus pedicatila bacillus) ), Barley powdery mildew (Erysiphe @ graminis), potato late blight (Phytophthora infestans), cucumber downy mildew (Pseudoperonospora @ cubensis), cucumber powdery mildew (Sphaepheaphy serophythae) togea), tomato ring spot fungus (Alternaria solani), radish white rust fungus (Alburo macrospora), vegetable sclerotium fungus (Sclerotinia sclerotiorum), apple scab fungus (Venturia inaequalis), Mochia stomach stomach and corn trophy Desert fungus (Colletotrichuum gloeosporioides), soybean purpura (Cercospora kikuchiii), sugar beet brown spot (Cercospora beticola), wheat wilt (Leptosphaeria ｕｍ ｕｍ ｄ ｕｍ ｏｒ ｏｒ ｕｍ) ingiberis), onion downy mildew (Peronospora destructor), corn spot fungus (Physoderma maydis), and the like.

Examples of phytopathogenic bacteria include, for example, Pseudomonas, Erwinia, Pectobacterium, Xanthomonas, Burkholderia, Streptomyces, Ralstonia, Clavibacter, Cirbacter, Chibibacillus, Chibibacir, Chibibacillum, Rhizomonas, and Rhizomonas , Acidovorax, Arthrobacter, and Rhodococcus. Preferred examples of the plant pathogenic bacteria include Xanthomonas genus, and among the Xanthomonas genus, Xanthomonas oryzae @ pv. @ Orizae is preferable.

Further, as the plant pathogenic virus, wheat-dwarf virus (Soil-born @ heat @ mosaic @ virus), soybean mosaic virus (Soybean @ mosaic @ virus), alfalfa mosaic virus (Alfalfa @ mosaic @ virus), potato leaf curl virus (Paurus virus) Mosaic virus (Cumber mosaic virus), tobacco mosaic virus (Tobacco mosaic virus), and the like.

植物 The plant disease control agent of this embodiment contains the compound represented by the formula (1) as an active ingredient. In the present specification, "containing at least one compound represented by the formula (1) as an active ingredient" means that at least one compound represented by the formula (1) is obtained in an amount such that a plant disease controlling effect can be obtained. If the compound represented by the formula (1) is contained as an active ingredient in the form of a free form, a hydrate, an optional solvate, a salt, or the like, the content is particularly preferable. Not limited.

When the plant disease controlling agent of the present embodiment is used as an active ingredient of an agricultural and horticultural disease controlling agent, the above-described compound may be used as it is, or in accordance with a conventional method of an agricultural and horticultural disease controlling agent. Pharmaceutically acceptable carriers such as solid carriers, liquid carriers, gaseous carriers, surfactants, and dispersants to form emulsions, solutions, suspensions, wettable powders, powders, granules, tablets, and oils. It may be used in the form of a composition (formulation) for controlling plant diseases in any dosage form such as aerosol, flowable and the like. The composition for controlling plant diseases may further contain other pharmaceutical auxiliaries.

担 体 Usable carriers include liquid carriers, solid carriers, gaseous carriers, surfactants, dispersants and the like. In addition, examples of the auxiliary agent for formulation include those usually used in a composition for controlling plant diseases.

Examples of the solid carrier include clays (carion clay, diatomaceous earth, bentonite, acid clay, etc.), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (selinite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.) ) And synthetic polymers such as starch, lactose, vinyl chloride polymers, and polyurethane.

Examples of the liquid carrier include alcohols (methanol, ethanol, isopropanol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, glycerin, etc.), ketones (acetone, methyl ethyl ketone, etc.), and aromatic hydrocarbons (benzyl, etc.). Alcohols, benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (paraffin, n-hexane, cyclohexane, kerosene, kerosene, etc.), ethers (diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diisopropyl ether, Diethyl ether, dioxane, tetrahydrofuran, etc.), esters (propylene carbonate, ethyl acetate, butyl acetate, benzyl benzoate, Isopropyl listinate, fatty acid esters of propylene glycol, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), amides (dimethylformamide, dimethylacetamide, N-methylpyrrolidone, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, etc.) Animal and vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, silicone oil, higher fatty acids, glycerol formal, water and the like.

As the gaseous carrier, LPG, air, nitrogen, carbon dioxide, dimethyl ether and the like can be mentioned.

Examples of surfactants and dispersants for emulsification, dispersion, spreading, and the like include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, and lignin. Sulfonates and the like are used. Further, as an auxiliary agent for improving the properties of the preparation, for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like are used.

The above carriers, surfactants, dispersants, and auxiliaries can be used alone or in combination as necessary.

The content of the plant disease controlling agent (the compound represented by the formula (1)) in the plant disease controlling composition is not particularly limited. 1 to 50% by mass, usually 1 to 50% by mass for wettable powders, usually 0.1 to 30% by mass for powders, usually 0.1 to 15% by mass for granules, and usually 0.1 to 10% by mass for oils For aerosols, the content is usually 0.1 to 10% by mass.

植物 The plant disease controlling agent or the plant disease controlling composition of the present embodiment may be used as it is, or may be used after being diluted as necessary.

The plant disease controlling agent or the composition for controlling plant diseases can be used together with other pesticides, for example, a resistance inducer and other pesticides may be mixed and sprayed, or separately. May be sprayed at different times or simultaneously.

Other pesticides include, for example, insecticides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers, and the like. Specifically, for example, the Pesticide Manual Thirteenth edition, issued by The British Crop Protection, Inc., and Shibuya Index (SHIBUYA INDEX, 13th edition, published in 2008, SHIBUYA INDEX RESEARCH, GROUP).

Examples of the insecticide include acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, prophenofrosyl, prophenofrosyl, profenofosyl, profenofosyl, profenofosyl, and fenofosyl. (methyl), chlorfenvinphos, demethon, dethion, ethione, malathion, malathion, coumaphos, isoxathion, fenthion, thiodin, diazinon, diazinon (Thiodicarb), aldicarb, oxamyl, propoxur, carbaryl, fenobcarb, ethiofencarb, ethiofencarbicarb, fenothiocarbicarbocarbocarbocarbocarbocarb Sulfan (carbosulfan), furatiothiocarb (furathiocarb), hyquincarb, alanicarb, methomyl, methomyl, benfracarb, carfuram, thioclam, thioclam Bensultap, dicofol, tetradifon, acrinathrin, bifenthrin, cycloprothrin, cyfluthrin, cyfluthrin, difluthrin, difluthrin, difluthrin (Fenfluthrin), fenpropathrin (imiproprin), imiprothrin, metofluthrin (metofluthrin), permethrin (permethrin), phenothrin (phenothrin), resmethrin (resmethrin) fluthrin, tetramethrin, tralomethrin, transfluthrin, cypermethrin, deltamethrin (deltamethalin, evahalatelin, cyhalafalin, cyhalafalin) Protox (ethofenprox), flufenprox, halfenprox, halfafluofen, silafluofen, cyromazine, diflubenzuron, teflubenzuron benzuron), flucycloxuron (flucycloxuron), flufenoxuron (flufenoxuron), hexaflumuron (hexaflumuron), lufenuron (lufenuron), novaluron (novaluron), Penfururon (penfluron), triflumuron (triflumuron), chlorfluazuron ( chlorfluazuron, diafenthiuron, methoprene, phenoxycarb, pyriproxyfen, halofenozide, tebufenozide, tebufenozide, tebufenozide nozide), chromafenozide (chromafenozide), dicyclanil (dicyclanil), buprofezin (buprofezin), hexythiazox (hexythiazox), amitraz (amitraz), chlordimeform (chlordimeform), pyridaben (pyridaben), fenpyroximate (fenpyroxymate), flufenerim (flufenerim), pyrimidifen ( pyrimidifen, tebufenpyrad, tolfenpyrad, fluacrylyprim, acequinocyl, cyflumetofen, fluflumetofen Amide (flubendiamide), ethiprole (ethiprole), fipronil (Fipronil), etoxazole (ethoxazole), imidacloprid (imidacloprid), nitenpyram (nitenpyram), clothianidin (c1othianidin), acetamiprid (acetamiprid), dinotefuran (dinotefuran), thiacloprid (thiacloprid), Thiamethoxam, pymetrozine, bifenazate, spirodiclofen, spiromesifen, flonicamid, chlorifamide Napir (chlorfenapyr), pyriproxyfen, indoxacarb, indoxacarb, pyridalyl, spinosad (spinosad), avermectin (avermectin), milbemycin nicotinin, milbemycin nicotinin (Rotenone), BT agent, entomopathogenic virus agent, emamectin benzoate (emamectinbenzoate), spinetoram (spinetoram), pyrifluquinazone (pyrifluquinazone), chlorantraniliprolol, and chlorantraniliprolol niliprole, cyenopyraphen, spirotetramat, lepimectin, metaflumizone, pyrafluno, pyraprome, pyraprome, pyraprome, pyraprome, pyraprome (Hydrmethylnon), triazamate, aphidopyopen, flupyrimin and the like.

Examples of the fungicide include azoxystrobin, kresoxim-methyl, trifloxystrobin, orysastrobin, picoxystrobin, floxtrostrobin and floxatrostrobin. ); Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil, etc .; zole), propiconazole, penconazole, flusilazole, microbutanil, cyproconazole, tecoconazole, tebuconazole, tebuconazole, tebuconazole, tebuconazole, tebuconazol Azole compounds such as (simeconazole); quinoxaline compounds such as quinomethionate; maneb, zineb, mancozeb, polycarbamate, and robineb, such as polycarbamate. Thiocarbamate compounds; phenylcarbamate compounds such as dietofencarb; organic chlorinated compounds such as chlorothalonil, quintozene; chlorinated compounds such as benomyl, benomyl, and thiophanate-membydembyl, etc. Benzimidazole compounds; phenylamides such as metalaxyl, oxadixyl, offurase, benalaxyl, furalaxyl, and chloroamide sulphamides such as chloroanilides such as cyprofuran (cyprofuram); Copper-based compounds such as cupric hydroxide and copper oxyquinoline; isoxazole-based compounds such as hydroxyisoxazole; and fosetyl-aluminium. And organophosphorus compounds such as tolclofos-methyl; N-halogenothioalkyl compounds such as captan, captafol, and folpet; procymidone and iprodione And dicarboximide compounds such as vinclozolin; flutranil Benzanilide compounds such as mepronil; morpholine compounds such as fenpropimorph and dimethomorph; organic tins such as triphenyltin hydroxide and triphenyltin acetate. Cyanopyrrole-based compounds such as fludioxonil and fenpiclonil; and others, fthalide, probenazole, acibenzolar S-methyl (cibenzilar-S-methyl), thiadinil, thiadinil, and thiazinyl. ), Carpropamide (carp) opamid), diclocymet, fenoxanil, tricyclazole, pyroquilon, ferimzone, fluozinam, fluoxinam, fluoxinam, simoxinil, simoxinil, simoxinil Fenarimol, fenpropidin, pencycuron, cyazofamide, cyflufenamide, cyscarfenamide, boscarid, penthiopyrad nazid), quinoxyfen (quinoxyfen), famoxadone (famoxadone), fenamidone (fenamidone), iprovalicarb (iprovalicarb), benthiavalicarb-isopropyl (benthiavalicarb-isopropyl), fluopicolide (fluopicolide), pyribencarb (pyribencarb), Furuchianiru (flutianil), isopyrazam (Isopyrazam), fenpicoxamide, kasugamycin, validamycin and the like.

Examples of the acaricide include bromopropylate, tetradifon, propargite, amitraz, fenothiocarb, hexothiazoxen, hexithiazoxin, hexithiazoxin, hexithiazoxin, hexithiazoxin, and hexithiazoxin. Dienochlor, fenpyroximate, tebufenpyrad, pyridaben, pyrimidifene, clofentezine, oxalzazole enprox), milbemectin (milbemectin), acequinocyl (acequinocyl), bifenazate (bifenazate), fluacrypyrim (fluacrypyrim), spirodiclofen (spirodichlofen), spiromesifen (spiromesifen), chlorfenapyr (chlorfenapyr), avermectin (avermectin), Shienopirafen (cyenopyrafen ), Cyflumetofen and the like.

Examples of the herbicides include phenoxy acid-based compounds such as cyhalofop-butyl and 2,4-D (2,4-dichlorophenoxyacetic acid); esprocarb, and desmedifam. Carbamate compounds such as alachlor, metolachlor and the like; acid amide compounds such as diachlor and metolachlor; urea compounds such as diuron and tebuthiuron; halosulfuron-methyl, frazas Sulfonylurea-based compounds such as flurasulfuron; pyrimidyloxybenzoic acid such as pyriminobac-methyl; Compound; glyphosate (glyphosate), bialaphos (bialaphos), glufosinate (glufosinate-ammonium) amino compounds such as and the like.

Examples of the plant growth regulator include an ethylene agent such as ethephon; an auxin agent such as indolebutyric acid, ethiclozate; a cytokinin agent; a gibberellin agent; an auxin antagonist; a dwarfant; And the like.

Examples of the fertilizer include nitrogenous fertilizers such as urea, ammonium nitrate, ammonium nitrate, and ammonium chloride; phosphate fertilizers such as lime superphosphate, ammonium phosphate, magnesium perphosphate, and magnesium phosphate; Potassium fertilizers such as potassium chloride, potassium bicarbonate, potassium nitrate, potassium nitrate and potassium sodium nitrate; manganese fertilizers such as manganese sulfate and manganese nitrate; boronaceous fertilizers such as boric acid and borate; Can be

In one embodiment, the present invention provides a method for controlling a plant disease, which comprises bringing the above-mentioned plant disease controlling agent or the above-mentioned compound into contact with a plant or a seed or containing the compound in a cultivation bed. The plant disease controlling agent or the compound described above may be used in the form of the composition for controlling a plant disease described above.

さ せ る When the above-mentioned plant disease controlling agent or the above-mentioned compound is brought into contact with a plant, it may be brought into contact with the foliage, root, rhizome, tuber, bulb, germinated bud and the like of the plant. The above-mentioned plant disease controlling agent or the above-mentioned compound may be brought into contact with plant seeds. Examples of the cultivation floor include soil, paddy water for growing rice, carriers for growing plants, water for hydroponics, and the like. Hydroponic water may contain nutrients.

In the method of the present embodiment, the method for contacting the above-mentioned plant disease controlling agent or the above-mentioned compound with a plant or a seed, or the method for containing it in a cultivation bed, is an application method generally applied in agriculture and horticulture. There is no particular limitation as long as there is foliage application, water application, soil treatment, nursery box application, seed treatment, immersion treatment, fertilizer mixing, watering for irrigation, and the like.

The application rate of the plant disease controlling agent of the present embodiment, in addition to the application method, in consideration of the application mode such as aerial spraying and ultra-trace spraying, depending on the type and severity of the target disease, the type of the target crop and the target site. , Can be determined.

For example, when the plant disease controlling agent is sprayed on the foliage of a plant, a solution prepared by diluting 1 to 1000 g of the formulation with 50 to 1000 L of water per 10 ares in the form of an emulsion, a wettable powder or a flowable agent is used. In the form of powder, about 1 to 10 kg of the preparation can be used per 10 ares.

When the plant disease controlling agent is applied to soil, for example, in the form of granules, about 1 to 10 kg per 10 ares can be used.

Hereinafter, the present invention will be described more specifically with reference to Examples, but the scope of the present invention is not limited to these Examples.

Hereinafter, the following abbreviations may be used in the embodiments.
ESI: Electrospray ionization method MS: Mass spectrum NMR: Nuclear magnetic resonance spectrum

Preparation Example 1
2,6-Difluoroisonicotinic acid (50 mg) was dissolved in chloroform (3.1 mL), and aniline (29 μL) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (65 mg), 4-dimethyl Aminopyridine (catalytic amount) was added, and the mixture was stirred at room temperature for 3 hours. Next, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated ammonium chloride, saturated sodium bicarbonate, and brine. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography (mobile phase: hexane / ethyl acetate = 50/1 to 8/1 (volume ratio)). There was obtained 66.3 mg of white powder of 6,6-difluoroisonicotinanilide.

Preparation Example 2
2,6-Dichloroisonicotinic acid (192 mg) was dissolved in acetonitrile (10 mL), and aniline (91 μL) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (208 mg), 4-dimethylaminopyridine (Amount of catalyst) was added, and the mixture was stirred at room temperature for 30 minutes. Next, water was added to the reaction solution, the precipitate was collected by filtration, and the precipitate was washed twice with water to obtain 238 mg of 2,6-dichloroisonicotinanilide as a white powder.

Example 1-1
2,6-Dichloroisonicotinanilide (50 mg) prepared in Preparation Example 2 was dissolved in tetrahydrofuran (1.9 mL), 55% sodium hydride (16 mg) was added, and the mixture was stirred at room temperature for 15 minutes. Acetyl chloride (27 μL) was added to this mixed solution, followed by stirring at room temperature for 1 hour. After adding water to the reaction solution and extracting with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was subjected to silica gel chromatography (mobile phase: hexane / ethyl acetate = 25/1 (volume)). Ratio)) to obtain 17.8 mg of a white powder of the compound of Example 1-1.

Example 1-8
2,6-Difluoroisonicotinanilide (50 mg) obtained in Preparation Example 1 was dissolved in tetrahydrofuran (1.9 mL), 55% sodium hydride (16 mg) was added, and the mixture was stirred at room temperature for 15 minutes. After benzoyl chloride (44 μL) was added to the mixed solution and stirred at room temperature for 2 hours, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography (mobile phase: hexane / ethyl acetate = 25/1 (volume ratio)). 27 mg of a white powder was obtained.

Preparation Example 3
2,6-Dichloroisonicotinic acid (960 mg) was dissolved in tetrahydrofuran (20 mL) and heated under reflux. Dimethyl sulfide borane (1.4 mL) was added dropwise to the solution, and the mixture was heated under reflux for 2 hours. Next, the reaction solution was cooled under ice-cooling, saturated sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel chromatography (mobile phase: hexane / ethyl acetate = 2/1 (volume ratio)) to obtain 801 mg of a white powder of 2,6-dichloro-4-pyridinemethanol. Was.

Example 2-6
The 2,6-dichloro-4-pyridinemethanol (45 mg) obtained in Preparation Example 3 was dissolved in acetonitrile (2.5 mL), and 3,4-dichloro-5-isothiazolecarboxylic acid (59 mg) and 1-ethyl -3- (3-Dimethylaminopropyl) carbodiimide hydrochloride (57 mg) and 4-dimethylaminopyridine (37 mg) were added, and the mixture was stirred at room temperature for 1 hour. Next, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography (mobile phase: hexane / ethyl acetate = 4/1 (volume ratio)). 13.8 mg of a white powder of the compound was obtained.

Example 1-25
Benzamide (111 mg) was dissolved in tetrahydrofuran (2.5 mL) and cooled to 0 ° C. After adding 55% sodium hydride (26 mg) to the solution and stirring at 0 ° C. for 15 minutes, 2,6-dichloroisonicotinic acid chloride (53 mg) was added and the mixture was stirred at 0 ° C. for 2 hours. Then, ethyl acetate (10 mL) was added to the reaction mixture, and the mixture was washed twice with saturated ammonium chloride (2 mL). The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and acetonitrile was added to the residue, and then water was added for crystallization to obtain 21.8 mg of a white powder of Example 1-25.

Example 1-9
2,6-Difluoroisonicotinanilide (117 mg) obtained in Preparation Example 1 was dissolved in acetonitrile (2.5 mL), and di-tert-butyl dicarbonate (131 mg) and 4-dimethylaminopyridine (catalytic amount) were added. In addition, the mixture was stirred at room temperature for 8 hours. Subsequently, water was added to the reaction mixture for crystallization to obtain 115 mg of a white powder of Example 1-9.

Preparation Example 4
2,6-Dichloroisonicotinic acid (1.9 g) was dissolved in thionyl chloride (10 mL) and heated under reflux for 4 hours. After the reaction mixture was cooled to room temperature and thionyl chloride was distilled off, it was dissolved in acetonitrile (20 mL) and added dropwise to 38% aqueous ammonia (20 ml). The reaction mixture was stirred at room temperature for 2 hours and then filtered to obtain 1.67 g of 2,6-dichloroisonicotinamide as a white powder.

Example 1-16
2,6-Dichloroisonicotinamide (95 mg) obtained in Preparation Example 4 was dissolved in tetrahydrofuran (5 mL) and cooled to 0 ° C. To the reaction mixture was added 55% sodium hydride (26 mg), and the mixture was stirred at 0 ° C for 1 hour. Subsequently, the reaction mixture was cooled to -78 ° C, 3,4-dichloroisothiazole-5-carbonyl chloride (108 mg) was added, and the mixture was stirred overnight while warming to room temperature. Water was added to the reaction mixture, which was extracted twice with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography (mobile phase: hexane / ethyl acetate = 50/1 to 8/1 (volume ratio)). This gave 13.6 mg of a white powder of -16.

Example 1-66
Thiobenzamide (343 mg) was dissolved in tetrahydrofuran (5 mL) and cooled to 0 ° C. To the solution was added 55% sodium hydride (131 mg), and the mixture was stirred at 0 ° C. for 15 minutes. Then, 2,6-dichloroisonicotinic acid chloride (104 mg) was added, and the mixture was stirred at 0 ° C. for 2 hours. Then, ethyl acetate (10 mL) was added to the reaction mixture, and the mixture was washed twice with saturated ammonium chloride (2 mL). The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography (mobile phase: hexane / ethyl acetate = 25/1 (volume ratio)). 5.1 mg of a colored powder was obtained.

The compounds shown in the following table were produced according to the above Preparation Examples and Examples.
The MS and ¹ H-NMR data of the compounds of the examples represented by the formulas (2 ″) and (3 ′) are also shown in the following table. Note that heavy chloroform was used as a solvent for ¹ H-NMR (400 MHz, 500 MHz or 600 MHz) measurement. MS was measured by the ESI-MS method.

[Example 11]
<Activity against rice blast>
An acetone solution of the following example compound prepared so as to have a concentration of 0.1 mg / mL or 1 mg / mL was diluted 10-fold with water, and 1/1000 volume of neoesterin was added. . The test solution obtained was sprayed on the two-leaf or three-leaf rice cultivated in a pot, and one day after spraying, the rice blast fungus (Pyricularia oryzae) was adjusted to 1.5 × 10 ⁵ to 5 × 10 ⁵ cells / mL. ) Was spray-inoculated and allowed to stand in a humid chamber (temperature 25 ° C, humidity 100%) for 24 hours. Then, the rice blast was cultivated in a plant cultivation chamber and the number of rice blast lesions formed on the second or third leaf was counted. The control value was calculated by the following formula based on the obtained number of lesions.
Control value = ((number of lesions in untreated area−number of lesions in treated area) / number of lesions in untreated area) × 100

The compounds of the following examples exhibited a control value of 70 or more at a concentration of 10 μg / mL, and the control effect on rice blast was confirmed.
1-1, 1-2, 1-3, 1-8, 1-11, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1- 29, 1-33, 1-65, 1-66, 1-67, 1-68, 2-3, 2-4, 2-5, 2-6

The compounds of the following examples exhibited a control value of 90 or more at a concentration of 100 μg / mL, and the control effect on rice blast was confirmed.
1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10

[Example 12]
<Growth disorders for rice>
An acetone solution of the following Example compound prepared to be 3.2 mg / mL was diluted 10-fold with water, and the diluted solution was used for the test. 0.25 mL of diluent was infiltrated per mL of soil. The seeds of the germinated rice were sown and cultivated in a plant cultivation chamber. The height of the single-leaved rice plant cultivated in this manner was measured, and the plant height ratio when the untreated plant height was set to 100 (hereinafter, referred to as “untreated plant height ratio”) was calculated. The presence or absence of growth inhibition was determined from these values.
All of the following example compounds showed growth at an untreated plant height ratio of 60 or more.
1-5, 1-10, 1-11, 1-12, 1-28, 1-30, 1-32, 1-36, 1-43, 1-50, 1-53, 1-54, 1- 56, 1-59, 1-61, 1-62, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7

[Comparative Example 1]
<Growth disorders for rice>
An acetone solution of the following comparative compound prepared to be 3.2 mg / mL was diluted 10-fold with water, and the diluted solution was used for the test. 0.25 mL of diluent was infiltrated per mL of soil. The seeds of the germinated rice were sown and cultivated in a plant cultivation chamber. The height of the single-leaved rice plant cultivated in this manner was measured, and the untreated plant height ratio was calculated, and is shown in the following table.

From the above results, it was confirmed that the use of the example compound significantly reduced the growth inhibition as compared with the comparative example compounds 1-1 to 1-5.

Example 13
<Growth disorders for rice>
An acetone solution of the following example compound prepared to be 0.2 mg / mL was diluted 10-fold with water, and the diluted solution was used for the test. 0.25 mL of diluent was infiltrated per mL of soil. The seeds of the germinated rice were sown and cultivated in a plant cultivation chamber. The plant height of the rice cultivated in the single leaf stage was measured, and the untreated plant height ratio was calculated. The presence or absence of growth inhibition was determined from these values.
All of the following examples showed growth at an untreated plant height ratio of 80 or more.
1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1- 13, 1-15, 1-25, 1-65, 1-67

[Comparative Example 2]
<Growth disorders for rice>
Acetone solutions of the above-mentioned comparative compounds 1-1, 1-2, 1-3, 1-4 and 1-5 each prepared to be 0.2 mg / mL were diluted 10-fold with water. The liquid was subjected to the test. 0.25 mL of diluent was infiltrated per mL of soil. The seeds of the germinated rice were sown and cultivated in a plant cultivation chamber. The following table shows the results of measuring the plant height of the single leaf stage rice cultivated in this way and calculating the untreated plant height ratio.

From the above results, it was confirmed that the use of the example compound significantly reduced the growth inhibition as compared with the comparative example compounds 1-1 to 1-5.

According to the present invention, it is possible to provide a plant disease controlling agent, a novel compound and a plant disease controlling method with reduced phytotoxicity. The plant disease controlling agent and the novel compound of the present invention have excellent resistance-inducing activity and are useful for controlling plant diseases.

Claims (8)

1. A compound represented by the following formula (1).
   

   

   In the formula (1), X ¹ and X ⁴ may be the same or different and represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, and ^one of X ¹ and X ⁴ is Represents a fluorine atom, a chlorine atom or a trifluoromethyl group, X ² and X ³ may be the same or different, and are a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group,
   X ^a is ^{a group} represented by the following formula (2) or (3);
   

   

   In the formula (2), Ja and Jb may be the same or different and represent an oxygen atom or a sulfur atom;
   G is
   An alkyl group having 1 to 12 carbon atoms which may be substituted with 1 to 3 groups selected from the group consisting of the following group C group, thiol group, methoxycarbonyl group and N-tert-butoxycarbonylamino group;
   An alkenyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
   An alkynyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
   An alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C,
   An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
   An alkylsulfonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following groups of group C,
   A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of group D below, a benzyl group, a phenyl group and a phenoxy group;
   A phenylsulfonyl group optionally substituted with 1 to 4 groups selected from the following group D groups:
   A phenyl group which may be substituted with 1 to 5 groups selected from the group consisting of the following group D, a phenoxy group and a benzyl group;
   5,6,7,8-tetrahydronaphthyl group,
   A naphthyl group or a heterocyclic group which may be substituted with 1 to 4 groups selected from the following group D,
   Wherein X ¹ and X ⁴ are both chlorine atoms, X ² and X ³ are both hydrogen atoms, and Aa is 1 to 5 members selected from the group consisting of group D below, phenoxy group and benzyl group G is a hydrogen atom when it is a phenyl group which may be substituted with a group or a heterocyclic group which may be substituted with 1 to 4 groups selected from the following group D.
   Aa is
   An alkyl group having 1 to 12 carbon atoms which may be substituted with 1 to 3 groups selected from the group consisting of the following group C group, thiol group, methoxycarbonyl group and N-tert-butoxycarbonylamino group;
   An alkenyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
   An alkynyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
   An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 groups selected from the following groups of group C,
   A phenyl group which may be substituted with 1 to 5 groups selected from the group consisting of the following group D, a phenoxy group and a benzyl group;
   5,6,7,8-tetrahydronaphthyl group,
   Naphthyl group,
   An alkenyloxy group having 2 to 4 carbon atoms,
   A phenyloxy group, or
   A heterocyclic group which may be substituted with 1 to 4 groups selected from the following group D,
   Aa is an alkyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C, or a group consisting of the following group D, phenoxy group and benzyl group When a phenyl group which may be substituted by 1 to 4 groups is shown, G is not a methyl group,
   When X ¹ is a chlorine atom, X ² , X ³ and X ⁴ are hydrogen atoms, Ja and Jb are simultaneously oxygen atoms, and G is an alkyl group having 1 to 4 carbon atoms, Aa is as follows: Not an alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 groups selected from the group C group,
   In the formula (3), Q represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH—, or a divalent group represented by the formula: —N (CH ₃ ) —,
   Ab is
   A phenyl group optionally substituted with 1 to 4 groups selected from the following group D groups, or a heterocyclic group optionally substituted with 1 to 4 groups selected from the following group D groups: Indicates that
   When X ¹ and X ⁴ are chlorine atoms, X ² and X ³ are hydrogen atoms, and Q is an oxygen atom, Ab represents an amino group, a trifluoromethyl group, a trifluoromethoxy group, an acetoxy group, a nitro group. A phenyl group substituted by only one group selected from the group consisting of a group and a cyano group; a phenyl group substituted by only one or two halogen atoms; a 2-thienyl group; a 3-furanyl group; Does not represent a 4-yl group; a 2-methylpyridin-3-yl group; or a 2-cyanopyridin-3-yl group;
   The heterocyclic group is a group selected from the following group E,
   The group C includes one to three groups selected from a halogen atom, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, and groups in the following group D. A pyridyl group which may be substituted with a phenyl group which may be substituted with 1 to 4 groups selected from the following group D;
   Group D includes a halogen atom, a hydroxyl group, an amino group, a methylthio group, an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, and 1 to 3 halogen atoms. Alkyloxy group having 1 to 4 carbon atoms, alkylcarbonyl group having 1 to 4 carbon atoms, methoxycarbonyl group, ethoxycarbonyl group, benzylaminocarbonyl group, acetoxy group, nitro group, cyano group, phenyl group, phenylcarbonyl Group and dimethylamino group,
   Group E includes pyridyl, thiazolyl, pyrazinyl, pyridazinyl, isoxazolyl, pyrimidinyl, benzimidazolyl, thienyl, furanyl, benzoxanyl, 2,3-dihydrobenzo [b] [1,4]. A dioxin-6-yl group, a dihydrothiazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a (1,1-dioxobenzo [d] isothiazol-3-yl) oxy group, a dibenzofuranyl group, an isothiazolyl group, and A group consisting of triazolyl groups.
2. The compound according to claim 1, wherein in the formula (1), X ¹ , X ² , X ³ and X ⁴ are a hydrogen atom, a fluorine atom or a chlorine atom.
3. The compound according to claim 1, wherein, in the formula (1), X ¹ and X ⁴ are the same and represent a fluorine atom or a chlorine atom, and X ² and X ³ are a hydrogen atom.
4. In the formula (1), X ^a is a group represented by the formula (2), in the formula (2), compound according to any one of claims 1 to 3 Ja is an oxygen atom.
5. The compound according to any one of claims 1 to 3, wherein in the formula (1), X ^a is a group represented by the formula (3), and in the formula (3), Q is an oxygen atom. .
6. The compound according to claim 5, wherein in the formula (3), Ab is a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D group.
7. 植物 A plant disease controlling agent comprising at least one of the compounds according to any one of claims 1 to 6 as an active ingredient.
8. The compound according to any one of claims 1 to 6, or the agent for controlling a plant disease according to claim 7, comprising foliage, soil, paddy water for growing rice, a carrier for growing plants, and nutrients. A method for controlling plant diseases by treating hydroponic water, plant roots, rhizomes, tubers, bulbs, germinated plants or seeds.