WO2020050297A1

WO2020050297A1 - Plant disease control agent

Info

Publication number: WO2020050297A1
Application number: PCT/JP2019/034715
Authority: WO
Inventors: 憲太朗山本; 聡畠山; 賢司梅村; 大貴永田; 友紀子瀧口
Original assignee: ＭｅｉｊｉＳｅｉｋａファルマ株式会社
Priority date: 2018-09-06
Filing date: 2019-09-04
Publication date: 2020-03-12
Also published as: TW202017906A

Abstract

Provided are a plant disease control agent and a plant disease control method, the plant disease control agent containing a compound represented by formula (1) as an active ingredient. (In the formula, X¹ and X⁴ each independently represent a fluorine atom or the like, X² and X³ each independently represent a hydrogen atom or a fluorine atom, Xa is a group represented by formula (2), (3), (4), (5) or (6), J represents an oxygen atom or the like, Q represents an oxygen atom or the like, A represents a phenyl group or the like which may have a substituent, Aa represents a piperidin-1-yl group or the like, Qb represents an oxygen atom or the like, Ab represents a hydrogen atom or the like, Z represents a hydrogen atom or the like, m represents an integer of 1-3, Ja and Jb each independently represent an oxygen atom or the like, G represents a phenyl group or the like, and Ad represents an alkyl group, an alkyloxy group, 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 control agent that protects plants from diseases caused by oomycetes and soil diseases.
The present application is filed in Japan with Japanese Patent Application No. 2018-166473 filed on Sep. 6, 2018, Japanese Patent Application No. 2018-171046 filed on Sep. 13, 2018, and on July 29, 2019. Priority is claimed based on Japanese Patent Application No. 2019-139210, 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 cuticle layer made of wax or the like, or a cell wall, and serves as a barrier for the entrance 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).

Inducing plant resistance in this way to protect plants from infection by phytopathogenic bacteria or phytopathogenic bacteria is very useful in growing healthy plants and securing food.
However, diseases caused by oomycetes, Fusarium spp., Pycium spp., Or Rhizoctonia spp. That occur in the soil cause withering and root rot symptoms of standing plants, yellowing and withering of the aerial parts of plants. No resistance inducer has been developed that has a sufficient disease control effect on soil diseases showing symptoms.

Diseases caused by oomycetes are one of the important diseases of crops, and control methods using fungicides are common. However, the fungicide is a disease that is difficult to control because it has a large environmental load and the presence of drug-resistant bacteria is known, so that the usable drug and the number of times that it can be used are limited.
In addition, soil diseases are generally controlled by soil disinfection, but pesticides used in these methods have a large environmental load. Furthermore, this control method requires a large amount of labor and involves dangerous work, so it is a disease that is difficult to control.
Therefore, if a resistance inducer for these diseases that can be used in spraying treatment or irrigation treatment is put to practical use, its usefulness as a simple and safe method is high.

It has been disclosed that isonicotinic acid derivatives have a plant controlling effect (Patent Documents 1 to 9). Among them, Patent Documents 1, 2, 7, 8, and 9 show effects on oomycetes, but it is known that plant disease control effect is sometimes weak. In addition, it is known that an isonicotinic acid compound has an effect of killing a plant (Patent Document 10), and it is known that phytotoxicity occurs in controlling plant diseases. On the other hand, in these documents, there is no specific description about the effect on soil disease.

JP-A-63-93766 JP-A-1-283270 JP-A-9-165374 JP-A-10-95772 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.

The present inventor has studied the fluorine-substituted pyridine compound in detail, and has found a compound that exhibits a high control effect on plant diseases by exhibiting resistance-inducing activity without directly exhibiting antibacterial activity against pathogenic bacteria. Completed the invention.

The present invention includes the following aspects.
(1) A plant disease controlling agent comprising a compound represented by the following formula (1) 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 any ^one of X ¹ and X ⁴ Represents a fluorine atom or a trifluoromethyl group, and 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, provided that X ¹ , X ² and When any one of X ⁴ represents a fluorine atom, any one of the other two does not represent a hydrogen atom;
X ^a is ^{a group} represented by the following formula (2), (3), (4), (5) or (6);

In the formula (2), J represents an oxygen atom or a sulfur atom,
A is
Carbon number which may be substituted by 1 to 3 groups selected from the group consisting of the following group C, thiol group, methoxycarbonyl group, ethoxycarbonyl group, methoxy group, and N-tert-butoxycarbonylamino group An alkyl group of 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 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,
Naphthyl group,
A heterocyclic group which may be substituted with 1 to 4 groups selected from the group D below, or a group represented by the following formula (2A):

In the formula (2A), X ¹ , X ² , X ³ and X ⁴ are the same as defined in the formula (1),
When A is a group represented by the formula (2A), Q is a divalent group represented by the formula: —O— (CH ₂ ) n—O—, and a formula: —NH— (CH ₂ ) n— A divalent group represented by O—, a divalent group represented by the formula: —NH— (CH ₂ ) _n —NH—, represented by a formula: —O—CH ₂ —CH ＝ CH—CH ₂ —O— A divalent group represented by the formula: —NH—CH ₂ —CH ＝ CH—CH ₂ —O—, a divalent group represented by the formula: —NH—CH ₂ —CH ＝ CH—CH ₂ —NH— Divalent group, cyclohexane-1,4-diyldioxy group, cyclohexane-1,4-diyldiamino group, divalent group represented by the formula: —NH— (cyclohexane-1,4-diyl) —O—, 1 , 3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, formula: -NH- (1 4-phenylene) divalent group represented by -O-, or a divalent group represented by the following formula (2B), n represents an integer of 2-8,

In the formula (2B), Gb is an oxygen atom, a sulfur atom, or a divalent group represented by the formula: —SO ₂ —,
When A is not a group represented by the formula (2A), Q represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH—, or a formula: —N (CH ₃ ) — A divalent group,
In the formula (3), Aa represents a piperidin-1-yl group, a 1-methyl-1-H-pyrrol-2-yl group, a morpholin-4-yl group, an indoline-1-yl group, a benzoisothiazole-3 (2H) -one-1,1-dioxide-2-yl group, piperazin-1-yl group, azetidin-1-yl group, 2,5-dioxopyrrolidin-1-yl group, 3-oxoisothiazole- 2 (3H) -yl group, benzo [d] isothiazol-2 (3H) -yl group, 1,1-dioxo-3-oxobenzo [d] isothiazol-2 (3H) -yl group, 5,6- A dihydro-4H-1,3-oxazin-2-yl group, a 1H-pyrrol-2-yl group or an isoindoline-2-yl group;
In the formula (4), Qb 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 hydrogen atom,
An alkyl group having 1 to 10 carbon atoms which may be substituted by 1 to 3 groups selected from the group consisting of the following group C, a methoxycarbonyl group and an 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,
A phenylcarbonyl group or a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D below;
In the formula (5), m represents an integer of 1 to 3, Z represents a hydrogen atom, a halogen atom or a methyl group,
In the formula (6), Ja and Jb may be the same or different and each 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;
Ad 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,
A naphthyl group or a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D below;
The heterocyclic group is a group selected from the following group E,
Group C includes a halogen atom, a hydroxyl group, an amino group, a cyano group, a 5-methyl-1,3-dioxol-2-one-4-yl group, an isothiazol-5-yl group, a phenylcarbonyl group; A pyridyl group optionally substituted with 1 to 3 groups selected from groups, and a phenyl group optionally 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 dimethylamino group, an acetylamino group, a methylthio group, a methylsulfonyl group, an alkyl group having 1 to 6 carbon atoms which may be substituted by 1 to 3 halogen atoms, An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, A group consisting of a nitro group 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, benzoisothiazol-3 (2H) -one-1,1-dioxydyl group, dibenzofuranyl group, isothiazolyl group, and triazolyl group It is a group consisting of
(2) The plant disease control agent according to (1), wherein in the formula (1), X ¹ , X ² , X ³ and X ⁴ are a hydrogen atom or a fluorine atom.
(3) The plant disease controlling agent according to (2), wherein in the formula (1), X ¹ and X ^{4 each} represent a fluorine atom, and X ² or X ³ is a hydrogen atom.
(4) The plant disease control agent according to (2), wherein in the formula (1), X ¹ and X ^{4 each} represent a fluorine atom, and X ² and X ³ are hydrogen atoms.
(5) In the formula (1), ^Xa is a group represented by the formula (2), and in the formula (2), J is an oxygen atom. The plant disease controlling agent according to any one of the above.
(6) In the formula (1), X ^a is a group represented by the formula (2), and in the formula (2), Q is a divalent group represented by the formula: —NH—. The plant disease control agent according to any one of (1) to (5), which is characterized by the following.
(7) In the above formula (1), ^Xa is a group represented by the above formula (2), and in the above formula (2), Q is an oxygen atom, wherein (1) to (5) The plant disease controlling agent according to any one of the above.
(8) In the above formula (1), ^Xa is a group represented by the above formula (2), and in the above formula (2), A is substituted by 1 to 3 groups selected from the group C group. An alkylcarbonyl group having 1 to 8 carbon atoms, which may be
An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the group C,
A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the group D, a benzyl group, a phenyl group and a phenoxy group;
A phenylsulfonyl group optionally substituted with 1 to 4 groups selected from the group D group, or 1 to 5 groups selected from the group consisting of the group D group, phenoxy group and benzyl group The plant disease controlling agent according to any one of (1) to (7), which is a phenyl group which may be substituted.
(9) In the formula (1), ^{X a} is a group represented by the formula (6), wherein the formula (6), Ja and Jb is an oxygen atom, (1) - The plant disease controlling agent according to any one of (4).
(10) A method for controlling plant diseases, which comprises contacting the plant disease controlling agent according to any one of (1) to (9) with a plant or a seed, or containing the agent in a cultivation bed.

According to the present invention, a plant disease controlling agent and a plant disease controlling method can be provided. The plant disease controlling agent of the present invention has excellent resistance-inducing activity, and is useful for controlling plant diseases (preferably, diseases caused by oomycetes or soil diseases).

In one embodiment, the present invention provides a plant disease controlling agent comprising a compound represented by the following formula (1) as an active ingredient. More preferably, the present invention provides a soil disease controlling agent containing a compound represented by the following formula (1) as an active ingredient. In one embodiment, the present invention provides 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 any ^one of X ¹ and X ⁴ Represents a fluorine 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. However, in formula (1), when any one of X ¹ , X ² and X ⁴ represents a fluorine atom, any one of the other two does not represent a hydrogen atom.

In the formula (1), X ¹ , X ² , X ³ and X ⁴ are preferably a hydrogen atom or a fluorine atom. Further, X ¹ and X ⁴ are preferably a fluorine atom. Further, it is preferable that X ² and X ³ is a hydrogen atom or a fluorine atom, it is preferable that at least one of X ² and X ³ are hydrogen atoms, more that X ² and X ³ are both hydrogen atoms preferable.

Ｘ In the formula (1), Xa is a group represented by the following formula (2), (3), (4), (5) or (6).

中 In the formula (2), J represents an oxygen atom or a sulfur atom, preferably an oxygen atom.

In the formula (2), A represents 1 to 3 groups selected from the group consisting of the following group C, thiol group, methoxycarbonyl group, ethoxycarbonyl group, methoxy group, and N-tert-butoxycarbonylamino group An alkyl group having 1 to 12 carbon atoms which may be substituted with; an alkenyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following group C; An alkynyl group having 2 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from groups; 1 carbon atom which may be substituted by 1 to 3 groups selected from the following group C To 8 alkylcarbonyl groups; 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; 1 to 3 alkyloxy groups selected from the following group C groups Alkyls having 1 to 8 carbon atoms which may be substituted by A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the following group D, a benzyl group, a phenyl group and a phenoxy group; A phenylsulfonyl group optionally substituted with 4 groups; a phenyl group optionally substituted with 1 to 5 groups selected from the group consisting of the following group D, phenoxy and benzyl; 6,7,8-tetrahydronaphthyl group; naphthyl group; a heterocyclic group which may be substituted with 1 to 4 groups selected from the following group D (where the heterocyclic group is selected from the following group E) Or a group represented by the following formula (2A) (in the formula (2A), X ¹ , X ² , X ³ and X ⁴ are the same as defined in the formula (1)). is there.

Among these, A is an alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C; 1 to 3 carbons selected from the following group C An alkyloxy group having 1 to 4 carbon atoms which may be substituted by a group represented by the following: an alkylsulfonyl group having 1 to 8 carbon atoms which may be substituted by 1 to 3 groups selected from the following group C: A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the following group D, a benzyl group, a phenyl group and a phenoxy group; 1 to 4 phenylcarbonyl groups selected from the following group D A phenylsulfonyl group optionally substituted with a group; a phenyl group optionally substituted with 1 to 5 groups selected from the group consisting of the following group D, phenoxy and benzyl; , 8-tetrahydronaphthyl group; naphthyl In formula ^{^{((2A), X 1, X}} 2, X 3 and ^{X 4} are the same as defined in the formula (1).) Or the following formula (2A) it is preferred that it is a group represented by .

In the above formula (2), when A is a group represented by the formula (2A), Q is a divalent group represented by the formula: —O— (CH ₂ ) n—O—, and the formula: —NH— A divalent group represented by (CH ₂ ) n—O—, a divalent group represented by the formula: —NH— (CH ₂ ) n—NH—, a formula: —O—CH ₂ —CH ＝ CH—CH Divalent group represented by ₂ -O-, divalent group represented by formula: -NH-CH ₂ -CH = CH-CH ₂ -O-, formula: -NH-CH ₂ -CH = CH-CH divalent groups represented by ₂ -NH-, cyclohexane-1,4-Jiirujiokishi group, cyclohexane-1,4-Jiirujiamino group of the formula: -NH- represented by (cyclohexane-1,4-diyl) -O- Divalent group, 1,3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, formula:- During H- (1,4-phenylene) -O- divalent group represented, or the following formula (2B) (the formula (2B), Gb represents an oxygen atom, a sulfur atom or the formula: -SO ₂ - at the indicated (Wherein n is an integer of 2 to 8), preferably a formula: —NH— (CH ₂ ) n—O— A divalent group represented by the formula: -NH- (CH ₂ ) n-NH-, a divalent group represented by the formula: -O-CH ₂ -CH = CH-CH ₂ -O- A valence group, or a 1,3-phenylenediamino group or a 1,4-phenylenediamino group, and n represents an integer of 2 to 4.

In the formula (2), when A is not a group represented by the formula (2A), Q is an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH—, or a formula: —N (CH ₃ ) A divalent group represented by-, preferably, an oxygen atom or a divalent group represented by the formula: -NH-.

In the formula (3), Aa represents a piperidin-1-yl group, a 1-methyl-1-H-pyrrol-2-yl group, a morpholin-4-yl group, an indoline-1-yl group, a benzoisothiazole-3 (2H) -one-1,1-dioxide-2-yl group, piperazin-1-yl group, azetidin-1-yl group, 2,5-dioxopyrrolidin-1-yl group, 3-oxoisothiazole- 2 (3H) -yl group, benzo [d] isothiazol-2 (3H) -yl group, 1,1-dioxo-3-oxobenzo [d] isothiazol-2 (3H) -yl group, 5,6- It represents a dihydro-4H-1,3-oxazin-2-yl group, a 1H-pyrrol-2-yl group or an isoindoline-2-yl group. Among these, Aa is a piperidin-1-yl group, a 1-methyl-1-1H-pyrrol-2-yl group, a morpholin-4-yl group, an indoline-1-yl group, or a benzoisothiazole-3 It is preferably a (2H) -one-1,1-dioxide-2-yl group.

In the formula (4), Qb 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 ) —, preferably oxygen Indicates an atom.
In the formula (4), Ab is a hydrogen atom; a carbon atom which may be substituted with 1 to 3 groups selected from the group consisting of the following group C, a methoxycarbonyl group and an N-tert-butoxycarbonylamino group. An alkyl group having the following formulas 1 to 10; an alkenyl group having 2 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the following group C groups; and 1 to 3 alkenyl groups selected from the following group C groups 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 which may be substituted by 1 to 3 groups selected from the following group C; A carbonyl group; or 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): Preferably a hydrogen atom or an alkyl carbonyl having 1 to 6 carbon atoms A group.

In the formula (5), m represents an integer of 1 to 3, preferably 1 or 2, and more preferably 1.
Z represents a hydrogen atom, a halogen atom or a methyl group, preferably a hydrogen atom.

中 In the formula (6), Ja and Jb may be the same or different and represent an oxygen atom or a sulfur atom.

In the formula (6), G represents a carbon atom which may be substituted by 1 to 3 groups selected from the group consisting of a group C shown below, a thiol group, a methoxycarbonyl group and an N-tert-butoxycarbonylamino group. An alkyl group of the following 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 groups; and 1 to 3 alkenyl groups selected from the following group C groups An alkynyl group having 2 to 8 carbon atoms which may be substituted with a group represented by the following: an alkylcarbonyl group having 1 to 8 carbon atoms which may be 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 which may be substituted with 1 to 4 groups selected from the group consisting of phenyl group and phenoxy group; which may be substituted with 1 to 4 groups selected from groups in the following group D Phenylsulfonyl group; phenyl group optionally substituted with 1 to 5 groups selected from the group consisting of group D below, phenoxy group and benzyl group; 5,6,7,8-tetrahydronaphthyl group; naphthyl Or 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).

In the formula (6), Ad represents a carbon atom which may be substituted with 1 to 3 groups selected from the group consisting of the following group C groups, thiol groups, methoxycarbonyl groups and N-tert-butoxycarbonylamino groups. An alkyl group of the following 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 groups; and 1 to 3 alkenyl groups selected from the following group C groups 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 which may be substituted with 1 to 5 groups selected from the group consisting of group D, phenoxy and benzyl; 5,6,7,8-tetrahydronaphthyl; naphthyl; Substituted with 1 to 4 groups selected from the group Which may be a Hajime Tamaki (wherein the heterocyclic group is a group selected from the following group E.) Shows a.

Group C includes a halogen atom, a hydroxyl group, an amino group, a cyano group, a 5-methyl-1,3-dioxol-2-one-4-yl group, an isothiazol-5-yl group, a phenylcarbonyl group; A pyridyl group optionally substituted with 1 to 3 groups selected from groups, and a phenyl group optionally substituted with 1 to 4 groups selected from the following group D, Preferably, it is substituted with 1 to 3 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. 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 dimethylamino group, an acetylamino group, a methylthio group, a methylsulfonyl group, an alkyl group having 1 to 6 carbon atoms which may be substituted by 1 to 3 halogen atoms, An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, A group consisting of a nitro group and a cyano group, preferably 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 by 1 to 3 halogen atoms, An alkyloxy group having 1 to 4 carbon atoms which may be substituted by up to 3 halogen atoms, an alkyl carb group having 1 to 4 carbon atoms Group, a methoxycarbonyl group, an ethoxycarbonyl group, benzylamino group, a group consisting of acetoxy group, a nitro group 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, benzoisothiazol-3 (2H) -one-1,1-dioxydyl group, dibenzofuranyl group, isothiazolyl group, and triazolyl group It is a group consisting of

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 methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-hexyl, n-hexyl, -Octyl group, n-dodecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc., preferably, methyl group, ethyl group, n-propyl group, isopropyl group, isobutyl group, tert-butyl group , Cyclopropyl, cyclohexyl, n-hexyl, n-octyl, n-dodecyl and the like.

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.

The divalent group represented by the formula: -NH- (cyclohexane-1,4-diyl) -O- is a group represented by the formula: -NH- and an oxygen atom at the 1- and 4-positions of the cyclohexane ring, respectively. It is a linked divalent group.

The divalent group represented by the formula: -NH- (1,4-phenylene) -O- means that a group represented by the formula: -NH- and an oxygen atom are bonded to the 1- and 4-positions of a benzene ring, respectively. It is a divalent group.

In the present specification, unless otherwise specified, a symbol "-" for bonding an atom and / or a group in a structural formula indicates a single bond, and "=" indicates a double bond. For example, in the formula (1), all symbols "-" indicate a single bond, and all symbols "=" indicate a double bond. For example, in the formula (2), Q is a divalent group represented by the formula: —O— (CH ₂ ) n—O—, and divalent represented by the formula: —NH— (CH ₂ ) n—O— A divalent group represented by the formula: —NH— (CH ₂ ) _n —NH—; a divalent group represented by the formula: —O—CH ₂ —CH ＝ CH—CH ₂ —O—; : A divalent group represented by —NH—CH ₂ —CH ＝ CH—CH ₂ —O—, a divalent group represented by the formula: —NH—CH ₂ —CH ＝ CH—CH ₂ —NH—, cyclohexane -1,4-diyldioxy group, cyclohexane-1,4-diyldiamino group, divalent group represented by the formula: —NH— (cyclohexane-1,4-diyl) —O—, 1,3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, formula: -NH- (1,4-phenylene ) In the case of a divalent group represented by -O- or a divalent group represented by the formula (2B), the symbol "-" in these groups indicates a single bond, and the symbol "=" indicates all divalent groups. Indicates a heavy bond.

In Group D, the alkyl group having 1 to 6 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, n-hexyl 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 may be substituted with a halogen atom, a hydroxyl group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, or one or two halogen atoms. A good pyridyl group, a phenyl group optionally having 1 to 2 substituents (preferably, the substituent is a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, One or two substituents selected from the group consisting of a methoxycarbonyl group and an acetoxy group), a cyano group, a thiol group, a methoxycarbonyl group, an ethoxycarbonyl group, a methoxy group, and an N-tert-butoxycarbonylamino group. An alkyl group having 1 to 12 carbon atoms which may have a group; an alkenyl having 2 to 6 carbon atoms which may be substituted with a halogen atom or a phenyl group with 1 to 2 groups; A alkynyl group having 2 to 6 carbon atoms; an alkyloxy group having 1 to 4 carbon atoms; and a halogen atom and an alkyl group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms. Phenylcarbonyl group optionally having 1 to 2 substituents selected; phenylsulfonyl group; halogen atom, hydroxyl group, amino group, dimethylamino group, acetylamino group, methylthio group, methylsulfonyl group, 1-3 Alkyl groups having 1 to 4 carbon atoms which may be substituted by one halogen atom, alkyloxy groups having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, An alkylcarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, a nitro group, a cyano group, a phenoxy group, and a substituent selected from the group consisting of a benzyl group; 5,6,7,8-tetrahydronaphthyl group; naphthyl group; an alkyl group having 1 to 4 carbon atoms, an alkyloxy group having 1 to 4 carbon atoms, a methoxycarbonyl group, And a heterocyclic group optionally having one or two substituents selected from the group consisting of a cyano group (preferably a pyridyl group, a thiazolyl group, a pyrazinyl group, a pyridazinyl group, an isoxazolyl group, a pyrimidinyl group, a benzimidazolyl group) A group selected from the group consisting of a group, a thienyl group, a 2,3-dihydrobenzo [b] [1,4] dioxin-6-yl group, a dihydrothiazolyl group, a benzothiazolyl group, a dibenzofuranyl group, and a triazolyl group Or represented by the formula (2A) (in the formula (2A), X ¹ , X ² , X ³ and X ⁴ are the same as defined in the formula (1)). And is preferably selected from the group consisting of an alkyloxy group having 1 to 4 carbon atoms; a halogen atom and an alkyl group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms. A phenylcarbonyl group optionally having 1 to 2 substituents; a phenylsulfonyl group; a halogen atom, a hydroxyl group, an amino group, a dimethylamino group, an acetylamino group, a methylthio group, a methylsulfonyl group, and 1 to 3 halongens An alkyl group having 1 to 4 carbon atoms which may be substituted by an atom, an alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, an alkylcarbonyl group having 1 to 4 carbon atoms 1 to 5 substituents selected from the group consisting of ethoxycarbonyl, benzylaminocarbonyl, nitro, cyano, phenoxy and benzyl And phenyl groups optionally; 5,6,7,8-tetrahydronaphthyl group; a naphthyl group; in the following formula (2A) (the formula ^{^{(2A), X 1, X}} 2, X 3 and ^{X 4} are the This is the same as the definition in Expression (1). Or a phenylcarbonyl group; or a halogen atom, a hydroxyl group, a dimethylamino group, an alkyl group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, It may have 1 to 2 substituents selected from the group consisting of an alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 halogen atoms, a nitro group, and a cyano group. More preferably, it is a phenyl group, or a phenyl group optionally having one substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms and an alkyloxy group having 1 to 4 carbon atoms. Is more preferable, or a phenyl group substituted with a dimethylamino group is even more preferable.

Alternatively, A is an alkylcarbonyl group having 1 to 8 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the group C; and 1 to 3 groups selected from the groups of the group C An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 4 groups selected from the group consisting of the group D, the benzyl group, the phenyl group and the phenoxy group A phenylcarbonyl group; a phenylsulfonyl group which may be substituted with 1 to 4 groups selected from the group D; or 1 to 4 selected from the group consisting of the group D, phenoxy and benzyl It is preferably a phenyl group which may be substituted with 5 groups, more preferably a phenyl group which may be substituted with 1 to 3 groups selected from groups in group D, and a halogen atom , Hydroxyl group, amino group A dimethylamino group, an acetylamino group, a methylthio group, a methylsulfonyl group, an alkyl group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, and 1 to 3 halogen atoms Selected from the group consisting of alkyloxy groups having 1 to 4 carbon atoms, alkylcarbonyl groups having 1 to 4 carbon atoms, ethoxycarbonyl groups, benzylaminocarbonyl groups, nitro groups, cyano groups, phenoxy groups, and benzyl groups. Even more preferably, it is a phenyl group optionally having 1 to 3 substituents.

In the formula (6), a more preferred embodiment of Ad 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; An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from groups in group C; and may be substituted with 1 to 3 groups selected from groups in group D A phenyl group; or a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D groups, and an even more preferred embodiment is an alkyl group having 1 to 4 carbon atoms; An alkyloxy group; or an isothiazolyl group optionally substituted with one or two halogen atoms. .

In the formula (6), 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 having 1 to 4 carbon atoms, or a phenyl group substituted with a cyano group; more preferably, a phenyl group or a phenyl group substituted with an alkyl group having 1 to 4 carbon atoms; Group.

において In the formula (6), a more preferred embodiment of Ja and Jb 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 this embodiment is produced, for example, according to the following methods A to O, but the production method of the compound of this 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 A is the same as defined in formula (2), Q ′ is an oxygen atom, a sulfur atom, and the formula: —NH A divalent group represented by-or a divalent group represented by the formula: -N (CH ₃ )-) in the presence or absence of a base in the presence of a condensing agent. Is done.

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. Compounds represented by the formula (51) are described, for example, in JP-A-63-93766 and JP-A-1-283270, R. E. Banks, et al., Heterocyclic polyfluoro-compounds. Part XII. Synthesis and some Reactions of 2,3,5,6-tetrafluoro-4-iodopyridine, can be synthesized by a method described in J. Chem. Soc. (C), 2091-2095 (1967), and the like.

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). The amount of the compound of the formula (52) to be used is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (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.

Method B

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) ) Is the same as the definition in formula (53), via the compound of formula (53) (in formula (53), X ¹ , X ² , X ³ and X ⁴ are the same as in definition in formula (1)). It can also be manufactured by the following method.

First, in the first step, the compound of the formula (53) is produced by chlorinating the compound of the formula (51).

溶媒 As the solvent used in the reaction, for example, tetrahydrofuran, toluene, ethyl acetate, dichloromethane, chloroform, acetonitrile and the like can be mentioned, but the reaction can 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., preferably in the range of 10 ° C. to 80 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 2 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 (52) in the presence of a base.

溶媒 Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and a mixed solvent thereof.

塩基 The base used for the reaction includes 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 carboxylic acid chloride (53).

使用 The amount of the compound represented by the formula (52) is in the range of 1 to 2 equivalents based on the carboxylic acid chloride (53). The reaction temperature is, for example, in the range of −20 to 100 ° C., preferably in the range of 10 to 50 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

Further, the compound represented by the formula (2 ′) can be obtained by adding a compound represented by the formula (51) to a solvent, a chlorinating agent, a compound represented by the formula (52) in the same container without isolating the compound represented by the formula (53). Can be also produced by adding and reacting a compound represented by the formula (1) and a base.

C method

Among the compounds represented by the formula (1), the compound represented by the formula (55) 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 (1) And a compound of the formula (54) (in the formula (54), A is the same as the definition in the formula (2) and X ⁵ represents a halogen atom) in the presence of a base. It can be produced by reacting.

溶媒 The solvent used for the reaction includes, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.

塩基 Examples of the base used in the reaction include sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide and the like. The amount of the base used is in the range of 1.0 to 1.5 equivalents based on the carboxylic acid (51).

使用 The amount of the compound represented by the formula (54) is in the range of 1 to 2 equivalents based on the carboxylic acid (51). The reaction temperature is, for example, in the range of −20 to 120 ° C., and preferably in the range of 10 to 80 ° C. The reaction time ranges from 10 minutes to 8 hours, preferably from 30 minutes to 6 hours.

D method

Among the compounds represented by the formula (1), the compound represented by the formula (55) 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 ( By reacting a compound represented by the formula (56) (where A is the same as defined in the formula (2)) in the presence of an acid. Can also be manufactured.

Examples of the solvent used in the reaction include tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and the like, but the reaction can also be performed without a solvent. .

The amount of the compound represented by the formula (56) is in the range of 1 to 10 equivalents based on the carboxylic acid (51).
The acid used in the reaction includes sulfuric acid, hydrogen chloride and the like, and the amount of the acid used is in the range of 0.01 to 3 equivalents based on the carboxylic acid (51).
The reaction temperature is, for example, in the range of −20 to 120 ° C., preferably in the range of 10 to 90 ° C. The reaction time ranges from 10 minutes to 8 hours, preferably from 30 minutes to 6 hours.

Method E

Among the compounds represented by the formula (1), the compound represented by the formula (71) 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 ( And the compound represented by the formula (57) (in the formula (57), Q ′ is 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 ) —, and E is a divalent group represented by the formula: — (CH ₂ ) n— (where n is an integer of 2 to 4) And a divalent group represented by the formula: —CH ₂ —CH ＝ CH—CH ₂ —, a cyclohexane-1,4-diyl group, a 1,4-phenylene group, or a formula (2B ′) shown below. (In the formula (2B ′), Gb represents an oxygen atom, a sulfur atom or a divalent group represented by the formula: —SO ₂ —)) in the presence or absence of a base. It can be produced by reacting in the presence of a condensing agent.

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). The amount of the compound represented by the formula (57) is in the range of 0.5 to 0.6 equivalent based on the carboxylic acid (51). The reaction temperature is, for example, in the range of 0 to 60 ° C, preferably in the range of 10 to 40 ° C. Reaction times range from 10 minutes to 24 hours, preferably from 30 minutes to 18 hours.

F method

Among the compounds represented by the formula (1), the compound represented by the formula (71) is a compound represented by the formula (53) (in the formula (53), X ¹ , X ² , X ³ and X ⁴ are represented by the formula ( Reaction of the compound of the formula (57) (wherein Q ′ and E are the same as the definition of the formula (57) in the above-mentioned Method E) in the presence of a base. It can also be manufactured by doing.

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

塩基 The base used for the reaction includes, for example, 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 carboxylic acid chloride (53).

使用 The amount of use represented by the formula (57) is in the range of 0.5 to 0.6 equivalent based on the carboxylic acid chloride (53). The reaction temperature is, for example, in the range of −20 to 100 ° C., preferably in the range of 10 to 50 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 4 hours.

G method

Among the compounds represented by the formula (1), the compound represented by the formula (59) 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 ( And the compound represented by the formula (58) (in the formula (58), X ⁵ represents a halogen atom, and E is the same as the definition of the formula (57) in the above-mentioned Method E). ) In the presence of a base.

塩基 Examples of the base used in the reaction include sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide and the like. The amount of the base used is in the range of 1.0 to 1.1 equivalent based on the carboxylic acid (51).

(4) The amount of the compound represented by the formula (58) is in the range of 0.5 to 0.6 equivalent based on the carboxylic acid (51). The reaction temperature ranges from -20 to 120 ° C, preferably from 10 to 80 ° C. The reaction time ranges from 10 minutes to 8 hours, preferably from 30 minutes to 6 hours.

H method

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 A compound represented by the formula (60) and a compound represented by the formula (60) (wherein Aa is the same as defined in the formula (3)) in the presence or absence of a base. It can be produced by reacting in the presence of a condensing agent.

溶媒 The solvent used for the reaction includes, for example, dichloromethane, chloroform, acetonitrile, ethyl acetate, toluene, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and the like.

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). The amount of the compound represented by the formula (60) is in the range of 1.0 to 1.2 equivalents based on the carboxylic acid (51). The reaction temperature ranges from 0 to 60 ° C, preferably from 10 to 40 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

I method

Among the compounds represented by the formula (1), the compound represented by the formula (3 ′) is a compound represented by the formula (53) (in the formula (53), X ¹ , X ² , X ³ and X ⁴ are represented by the formula The same as defined in (1)) and a compound represented by the formula (60) (wherein Aa is the same as defined in the formula (3)) in the presence of a base. Can also be manufactured.

溶媒 Solvents used for the reaction include, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and a mixed solvent thereof.

使用 The amount of the compound represented by the formula (60) is in the range of 1 to 2 equivalents based on the carboxylic acid chloride (53). The reaction temperature ranges from -20 to 100 ° C, preferably from 10 to 50 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 4 hours.

J method

Among the compounds represented by the formula (1), the compound represented by the formula (4 ′) 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) can be 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 80 ° C, preferably in the range of 0 to 40 ° 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 represented by the formula (61) and the compound represented by the formula (54) (in the formula (54), Ab is the same as defined in the formula (4), and X ⁵ is halogen) (Indicating an atom) in the presence of a base to produce a compound represented by the formula (4 ′).

溶媒 The solvent used for the reaction includes, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and mixtures thereof.

塩基 The base used for the reaction includes 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 represented by the formula (61).

使用 The amount of the compound represented by the formula (54) is in the range of 1 to 2 equivalents based on the compound represented by the formula (61). The reaction temperature is in the range of −20 to 100 ° C., preferably in the range of 10 to 60 ° C. Reaction times range from 10 minutes to 6 hours, preferably from 30 minutes to 3 hours.

K method

Among the compounds represented by the formula (1), the compound represented by the formula (5 ′) is a compound represented by the formula (53) (in the formula (53), X ¹ , X ² , X ³ and X ⁴ are represented by the formula (Same as the definition in (1)) and a compound represented by the formula (62) (in the formula (62), X ⁵ represents a halogen atom, L represents a hydrogen atom or a methyl group, and n represents 1 to Is represented by an integer of 3) in the presence of a base.

溶媒 The solvent used for the reaction includes, for example, tetrahydrofuran, toluene, ethyl acetate, acetonitrile, dichloromethane, chloroform, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and a mixed solvent thereof.

使用 The amount of the formula (62) is in the range of 1 to 2 equivalents based on the carboxylic acid chloride (53). The reaction temperature ranges from -20 to 100 ° C, preferably from 10 to 90 ° C. The reaction time ranges from 10 minutes to 10 hours, preferably from 30 minutes to 8 hours.

L method

Among the compounds represented by the formula (1), the compound represented by the formula (3 ′) is a compound represented by the formula (53) (in the formula (53), X ¹ , X ² , X ³ and X ⁴ are A compound represented by formula (1)) and a compound represented by formula (60) (in formula (60), Aa is the same as defined in formula (3)) in the presence or absence of an acid. It can also be produced by reacting in the presence.

The solvent used for the reaction includes, for example, toluene, dichloromethane, chloroform, dichloroethane, N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, nitromethane, nitrobenzene, and a mixed solvent thereof. it can.

Examples of the acid used in the reaction include aluminum trichloride, aluminum tribromide, lanthanoid triflate, zeolite, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, hydrochloric acid, paratoluenesulfonic acid, iron trichloride, zinc dichloride, and polyphosphoric acid. Acids, titanium tetrachloride, titanium tetrabromide, tin chloride, zinc trifluoromethanesulfonate, and the like. The amount of the acid used is in the range of 0.01 to 10 equivalents based on the carboxylic acid chloride (53).

使用 The amount of the compound represented by the formula (60) is in the range of 0.5 to 2 equivalents based on the carboxylic acid chloride (53). The reaction temperature is in the range of -20 to 250 ° C, preferably in the range of 10 to 100 ° C. Reaction times range from 10 minutes to 48 hours, preferably from 30 minutes to 16 hours.

M method

Among the compounds represented by the formula (1), the compound represented by the formula (6 ′) 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 the formula (63) (wherein G is the same as in the definition of the formula (6)). 65) (in formula (65), Ad is the same as defined in formula (6), and Jb represents an oxygen atom or a sulfur atom).

First, in the first step, the compound of the formula (64) is produced by reacting the compound of the formula (51) with the compound of the formula (63) in the presence or absence of a base in the presence of a condensing agent.

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 (63) is in the range of 1 to 5 equivalents based on the compound represented by the formula (51).

Next, in the second step, the compound of the formula (6 ') can be produced by reacting the compound of the formula (64) with the compound of the formula (65) 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 (64).

使用 The amount of the compound represented by the formula (65) is in the range of 1 to 5 equivalents based on the compound represented by the formula (64).

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.

N law

Among the compounds represented by the formula (1), the compound represented by the formula (6 ′) is a compound represented by the formula (64) and a compound represented by the formula (66) (In the formula (66), Ad is the definition in the formula (6)) And Jb represents an oxygen atom or a sulfur atom.).

That is, the compound represented by the formula (6 ') can be produced by reacting the compound of the formula (64) with the compound of the formula (66) in the presence of a base.

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 (64).

使用 The amount of the compound represented by the formula (66) is in the range of 1 to 5 equivalents based on the compound represented by the formula (64).

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.

O method

Among the compounds represented by the formula (1), the compound represented by the formula (6 ′) is a compound represented by the formula (53) (in the formula (53), X ¹ , X ² , X ³ and X ⁴ are represented by the formula (1) )) And a compound of the formula (67) (in the formula (67), G and Ad have the same definitions as in the formula (6), and Jb represents an oxygen atom or a sulfur atom.) Is also produced by reacting

That is, the compound represented by the formula (6 ') can be produced by reacting the compound of the formula (53) with the compound of the formula (67) in the presence of a base.

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 (67).

使用 The amount of the compound represented by the formula (67) is in the range of 1 to 5 equivalents based on the compound represented by the formula (53).

Specific Compound Represented by Formula (2 ″) Among the compounds represented by Formula (1), specific embodiments of the compound represented by the following Formula (2 ″) are shown in the following table.
As specific compounds represented by the formula (2 ″), X ¹ , X ² , X ³ and X ⁴ are combinations of the substituents shown in Table 1 below, and Q and A are represented by Tables 2 to 9 And a compound which is a combination of substituents represented by J represents an oxygen atom or a sulfur atom.

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

Among the compounds represented by the formula (2 ″), examples of the compound in which A is a group represented by the formula (2A) include X ¹ , X ² , X ^3, and X ^{4 each} having a substituent represented by the following Table 10. Q is a divalent group represented by the formula: —O— (CH ₂ ) n—O—, a divalent group represented by the formula: —NH— (CH ₂ ) n—O—, : A divalent group represented by —NH— (CH ₂ ) _n —NH—, a divalent group represented by the formula: —O—CH ₂ —CH ＝ CH—CH ₂ —O—, a formula: —NH— A divalent group represented by CH ₂ —CH ＝ CH—CH ₂ —O—, a divalent group represented by the formula: —NH—CH ₂ —CH ＝ CH—CH ₂ —NH—, cyclohexane-1,4 -Diyldioxy group, cyclohexane-1,4-diyldiamino group, 2 represented by the formula: -NH- (cyclohexane-1,4-diyl) -O- Divalent group, 1,3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, divalent group represented by the formula: -NH- (1,4-phenylene) -O- And a compound which is a divalent group represented by the formula (2B).

Specific compound represented by formula (3 ') Table 11 below shows specific embodiments of the compound represented by formula (3') among the compounds represented by formula (1).

As a specific compound represented by the formula (3 ′), X ¹ , X ² , X ³ and X ⁴ are a combination of substituents shown in Table 11 below, and Aa is a piperidin-1-yl group, 1-methyl-1-1H-pyrrol-2-yl group, morpholin-4-yl group, indoline-1-yl, benzoisothiazol-3 (2H) -one-1,1-dioxide-2-yl, piperazine -1-yl group, azetidin-1-yl group, 2,5-dioxopyrrolidin-1-yl group, 3-oxoisothiazol-2 (3H) -yl group, benzo [d] isothiazol-2 (3H ) -Yl group, 1,1-dioxo-3-oxobenzo [d] isothiazol-2 (3H) -yl group, 5,6-dihydro-4H-1,3-oxazin-2-yl group, 1H-pyrrole -2-yl group or isoindori And n-2-yl groups.

Specific compounds represented by the formula (5 ″) Specific embodiments of the compounds represented by the formula (5 ″) among the compounds represented by the formula (1) are shown in Tables 12 and 13 below.

As a specific compound represented by the formula (5 ″), X ¹ , X ² , X ³ and X ⁴ are a combination of substituents shown in Table 12 below, a substituent of Z and its substitution position, Compounds wherein m is a combination shown in Table 13 below.

Specific Compounds Represented by Formula (6 ″) Specific embodiments of the compounds represented by Formula (6 ″) among the compounds represented by Formula (1) are shown in Tables 14 to 19 below.

As a specific compound represented by the formula (6 ″), X ¹ , X ² , X ³ , X ⁴ , Ja and Jb are combinations of the substituents shown in Tables 14 and 15 below, and Ad is Compounds in which Tables 16 to 17 and G are combinations of the substituents shown in Tables 18 to 19 are included.

Plant pathogen The plant pathogen to be controlled by the plant disease controlling agent of the present embodiment is not particularly limited, and includes, for example, fungi, bacteria, actinomycetes, viruses, and the like, particularly in oomycetes and soil. Fungi that inhabit the sea.

Examples of the phytopathogenic fungi include, for example, Pythium 枯 ultimum, vegetable wilt fungus (Rhizoctonia solani), Chinese cabbage rot fungus (Rhizoctonia solani), cucumber vine rot fungus (Fusarium umyos) Fusarium oxysporum, lettuce root rot fungus (Fusarium oxysporum), cucurbit homopsis root rot fungus (Phomopsis scleroticoides), cruciferous vegetable root rot fungus (Plasmodiosapora spore spore spore spore spore spore spore spore fungus) Purple crested wilt fungus (Helicobasidum @ mompa), fruit tree white crested feather Fungus (Rosellinia necatrix), soybean wilt fungus (Sclerotium rollsii), tomato brown root rot (Pyrenochaeta lycopersici), wheat streak (Cephalosporium ｒｅｙｍｉｎｙｐｈａｔｐｈａｔａｔｐｈ) , Soybean black root rot fungus (Cylindrocladium @ crotalariae), snow rot brown small-grain rot fungus (Typhula @ incarnata), snow rot black rot bacillus (Typhula @ ishikariensis), sugar beet root-knot fungus (Aphanoecoichoma tobacco) sis @ basicola, wheat wilt fungus (Gaeumanonomyces @ graminis), pear black spot fungus (Alternaria @ alternata), pear black spot fungus (Alternaria @ kikutiana), gray mold fungus (Botrytis stomach) Anthrax fungus (Colletotrichum amentarium), cucumber gray plague fungus (Phytophthora capsici), cucumber anthrax bacillus (Colletotrichum lagenarium), tomato wilt fungus (Fusarium oxysporium germophilus gypsifi. berella @ fujikuroi, grape downy mildew (Plasmopara @ viticola), grape late-rot fungus (Glomerella @ singulata), rice blast fungus (Pyricularia @ oryzae), rice seedling wilt (Pythium stomach germ) Potato half-blight wilt fungus (Verticillium albo-atrum), wheat rust (Puccinia recondita), barley powdery mildew (Erysiphe graminis), potato blight (Phytophthora ｆキュべｆｆｆｆＰ) Uri powdery mildew (Sphaerotheca @ fuliginea), watermelon plague (Phytophthora @ cryptogea), tomato ring spot fungus (Alternaria @ solani), radish white rust fungus (Alburo @ macrospora), vegetable rot fungus, spore fungus of spores of spores inaequalis), peach ash star fungus (Monilinia fructicola), strawberry anthracnose fungus (Colletotrichum gloeosporioides), soybean purpura fungus (Cercospora kikuchii), sugar beet brown spot fungus (Cercospora beticola), wheat glume blotch fungus (Leptosphaeria nodorum), wheat powdery mildew (Blumeria graminis), cabbage seedling blight (Pythium zingiberis), onion downy mildew (Peronospora destructor), corn leaf spot (Physoderma maydis), and the like.

Particularly preferred examples of the phytopathogenic fungi include potato blight fungus (Phytophthora infestans), cucumber downy mildew (Pseudoperonospora cubensis), grape downy mildew (Plasmopara viticola), cucumber gray blight fungus (Phycium phytoa phyto phytoa phytoa phyto phyto phyto phyto phyto phyto phyto phyto phytophyto) and a phytophytic phytophyte phytophyte phytophyte phytophytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte phytophyte fungus). Disease germs (Pythium graminicola), cabbage seedling wilt (Pythium zingiberis), onion downy mildew (Peronospora destructor), Japanese radish white rust (Alburo thyromatophyte, Vegetable phytophyr phytophyr, phytophyr phyrophyra, phytophyr phytophyr) ultimum), corn spot disease (P hydosterma maydis) and soybean stem blight (Phytophthora sojae).
Alternatively, other preferable examples of the phytopathogenic fungi include, for example, Pythium ultimum, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, and Curcuma wilt fungus (Rhizoctonia solani). Fusarium oxysporum, vegetable wilt fungus (Fusarium oxysporum), lettuce root rot fungus (Fusarium oxysporum), cucurbit homopsis root rot fungus (Phomopsis scleroticoides, Brassicaceae scabrios spellicae spores) (Spongospora subterranea), orchard purple root rot fungus (Helicobasidum momba), orchard White rot fungus (Rosellinia necatrix), soybean white silk rot (Sclerotium rolfsii), tomato brown root rot (Pyrenochaeta lycopersici), wheat streak rot (Cephalosporium graminea germ) Cylindrocladium crotalariae, snow rot brown sclerotium bacillus (Typhula incarnata), snow rot black sclerotium bacillus (Typhula ishikariensis), sugar beet seedling wilt (Aphanomyces cochlioides bacillus) (Gaeumanon omyces graminis).

Examples of phytopathogenic bacteria include, for example, Pseudomonas, Erwinia, Pectobacterium, Xanthomonas, Burkholderia, Streptomyces, Ralstonia, Clavibacter, Cirbacter, Chibibacil, Cirobacterium, and Genus Rhizomonas , Acidovorax, Arthrobacter, and Rhodococcus. Preferred examples of the phytopathogenic bacteria include the genus Pseudomonas, the genus Agrobacterium, the genus Ralstonia, and the genus Erwinia.

The phytopathogenic actinomycetes include Streptomyces genus.

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 (Pautrovirus) 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 the compound represented by the formula (1) as an active ingredient" means that the compound represented by the formula (1) is contained in such an amount that a plant disease controlling effect can be obtained. The content of the compound represented by formula (1) is not particularly limited as long as it contains the compound represented by the formula (1) in the form of a free form, a hydrate, an optional solvate, a salt or the like as an active ingredient.

When the plant disease controlling agent of the present embodiment is used as an active ingredient of an agricultural and horticultural plant disease controlling agent, the above-mentioned compound may be used as it is, or may be used in accordance with a conventional method of agricultural and horticultural disease controlling agent. Horticulturally acceptable carriers, for example, solid carriers, liquid carriers, gaseous carriers, surfactants, mixed with dispersants, emulsions, solutions, suspensions, wettable powders, powders, granules, tablets, It may be used in the form of a composition (formulation) for controlling plant diseases in any dosage form such as oils, aerosols, flowables 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.) And 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, auxiliaries for improving the properties of the preparation include, for example, carboxymethylcellulose, gum arabic, polyethylene glycol, calcium stearate and the like.

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 a plant disease can be used together with other pest controlling agents.For example, a resistance inducer and another pest controlling agent 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 17th edition, "British Crop Protection" issued by Shibuya INDEX, 17th edition, 2014, SHIBYA INDEX RESEARCH issued by 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, niliprole, cyenopyraphen, spirotetramat, lepimectin, metaflumizone, pyrafluno, pyraprome, pyraprome, pyraprome, pyraprome, pyraprome (Hydramethylnon), triazamate, aphidopyopen, flupyrimin and the like.

Examples of the fungicide include azoxystrobin, kresoxim-methyl, trifloxystrobin, orysastrobin, picoxystrobin, and fluoxastrobin. ), Etc .; ananilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil, etc .; triadimefon, bitertanol, flitumisol, triflumethanol, triflumethanol, triflumethanol, triflumitolol nazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole, tecoconazole, tecoconazole, tebuconazole, tebuconazole, tebuconazole, tebuconazole Azole compounds such as (simeconazole); quinoxaline compounds such as quinomethionate; maneb, zineb, mancozeb, polycarbamate, robinebep Dithiocarbamate compounds; phenylcarbamate compounds such as dietofencarb; organic chlorinated compounds such as chlorothalonil, quintozene; benomyl, thiophanate-m-benzyl-m-benzyl, thiophanate-m-benzyl, thiophanate-m-benzyl, thiophanate-m-benzyme-m-benzyl-m-thiophenate, and thiophanate-m-benzyme-m-benzyl-m-benzamide Phenylamides such as metalaxyl, oxadixyl, offurase, benalaxyl, furalaxyl, and chloroamides such as chloroamide (cyprofuran) such as metalaxyl, oxadixyl, offurase, benalaxyl, furalaxyl, and cyprofuran (cyprofuram); S Rufenic acid compounds; copper compounds such as cupric hydroxide and copper oxyquinoline; isoxazole compounds such as hydroxyisoxazole; fosetyl aluminum (fosethyl-aluminium); Organophosphorus-based compounds such as tolclofos-methyl; N-halogenothioalkyl-based compounds such as captan, captafol, and folpet; procymidone, iprodion, iprodione Dicarboximide compounds such as vinclozolin; flutolani ), Benzanilide compounds such as mepronil; morpholine compounds such as fenpropimorph, dimethomorph; triphenyltin hydroxide, fentin acetate, etc. Organotin compounds; cyanopyrrole compounds such as fludioxonil and fenpiclonil; others, fthalide, probenazole, acibenzolar S-methyl (cibenzollar-S-methyl), thiadinyl, thiadinil. (Isotianil), carpropamide (ca propamid, diclocymet, phenoxanil, tricyclazole, pyroquilon, ferimzone, fluozinam, fluoxinam, pyroxinam, fluoxinam, fluoxinam, fluoxinam, fluoxinam, fluoxinam, fimozin, fyoxinam, simoxin, fymozin, ymoxin, fimonizin Fenarimol, fenpropidin, pencycuron, cyazofamide, cyflufenamide, cyscarfenamide, boscarid, penthiopyrad uinazid), quinoxyfen (quinoxyfen), famoxadone, fenamidone (fenamidone), iprovalicarb (iprovalicarb de), bentiavaricarb depib (bentiavalipibol, fluentalpib, futivalpib) (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, 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-based compounds such as pyriminobac-methyl Compounds: Amino acid compounds such as glyphosate, bialaphos, glufosinate-ammonium 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, magnesia perphosphoric acid, 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 may be used in the form of the plant disease controlling composition described above.

させる When the above-mentioned plant disease controlling agent 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 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 of contacting the above-mentioned plant disease controlling agent with a plant body or a seed, or the method of containing it in a cultivation bed is not particularly limited as long as it is an application method generally applied in agriculture and horticulture. However, for example, foliage application, water surface application, soil treatment, seedling box application, seed treatment, immersion treatment, fertilizer mixing, irrigation water mixing, and the like can be mentioned.

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, wettable powder or flowable agent is used. In the form of powder, about 1 to 10 kg of the preparation can be used per 10 ares.

用 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 IR: Infrared absorption spectrum n: Normal tert: Tertiary

Example 1
2,3,6-Trifluoroisonicotinic acid (1.76 g) was dissolved in N, N-dimethylformamide (10 mL), and bromoethane (1.08 g) and potassium carbonate (1.38 g) were added to the solution. In addition, the mixture was stirred at 80 ° C. for 2 hours. Next, the reaction mixture was returned to room temperature, ethyl acetate was added, and the mixture was extracted with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain the compound of Example 1-117 (yield 1.44 g).

Example 2
2,3,6-Trifluoroisonicotinic acid (5.28 g) was dissolved in thionyl chloride (30 mL) and heated under reflux for 1 hour. After concentrating this reaction product, it was dissolved in acetonitrile (30 mL), 3-chloro-4-methylaniline (5.64 g) and pyridine (3.20 g) were added, and the mixture was heated under reflux for 1 hour. Next, the reaction mixture was returned to room temperature, ethyl acetate was added, and the mixture was washed with 1N hydrochloric acid and 1N sodium hydroxide in that order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to give the compound of Example 1-30 (yield 7.70 g).

Example 3
Dissolve 2,3,6-trifluoro-4-pyridinemethanol (106 mg) in dichloromethane (8 mL), add acetyl chloride (65 mg) to the solution, cool to 0 ° C., and add N, N-diisopropyl Ethylamine (130 mg) was added, and the mixture was stirred at room temperature overnight. Next, after the solvent was distilled off, the residue was dissolved in diethyl ether, washed sequentially with saturated sodium carbonate, 2% hydrochloric acid and saturated saline, and the organic layer was dried over anhydrous magnesium sulfate. After evaporating the solvent with an evaporator, the residue was purified by silica gel chromatography to obtain the compound of Example 3-1 (yield 63.2 mg).

Example 4
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) were added to the solution. ) And 4-dimethylaminopyridine (catalytic amount) were 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 and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to give the compound of Example 1-143 (yield 66.3 mg).

Example 5
2,3,6-Trifluoroisonicotinic acid (30 mg) was dissolved in chloroform (3.1 mL), and ethylenediamine (6.0 μL) and 1-ethyl-3- (3-dimethylaminopropyl) were added to the solution. Carbodiimide hydrochloride (38 mg), 1-hydroxybenzotriazole (27 mg), and triethylamine (30 μL) were added, and the mixture was stirred at room temperature overnight. Again, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (38 mg) and 1-hydroxybenzotriazole (27 mg) were 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 and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to obtain the compound of Example 1-150 (yield: 20.1 mg).

Example 6
2,3,6-Trifluoroisonicotinic acid (100 mg) was dissolved in N, N-dimethylformamide (5.6 mL), and 2-chloroethylamine hydrochloride (79 mg) and 1-ethyl-3- (3-dimethyl (Aminopropyl) carbodiimide hydrochloride (128 mg), 1-hydroxybenzotriazole (92 mg), and triethylamine (101 μL) were 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 and saturated sodium hydrogen carbonate. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by silica gel chromatography to obtain N- (2-chloroethyl) -2,3,6-trifluoroisonicotinamide (yield). 100 mg).

The N- (2-chloroethyl) -2,3,6-trifluoroisonicotinamide (20 mg) obtained above was dissolved in tetrahydrofuran (8.4 mL), and 55% sodium hydride (3. 8 mg) and stirred for 3 hours. Next, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography to give the compound of Example 4-2 (yield 16 mg).

Example 7
2,6-Difluoroisonicotinic acid (80 mg) is dissolved in acetonitrile (1 mL), and cyclohexyl alcohol (50 mg) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (96 mg) are dissolved in the solution. And 4-dimethylaminopyridine (61 mg) were added, and the mixture was stirred at room temperature for 24 hours. Next, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was purified by Preparative TLC to give the compound of Example 1-205 (yield 42 mg).

Example 8
2,3,6-Trifluoroisonicotinic acid (177 mg, 1.0 mmol) was dissolved in dichloroethane, thionyl chloride (1 mL) was added to the solution, and the mixture was heated under reflux and stirred for 2 hours. After evaporating the solvent of the reaction product with an evaporator, nitromethane (3 mL), 1-methylpyrrole (54 mg, 0.67 mmol), and zinc (II) trifluoromethanesulfonate (24 mg, 0.066 mmol) were added, and the mixture was added at room temperature. Stirred overnight. After sodium hydrogen carbonate was added to the reaction mixture, water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off by an evaporator, and the residue was purified by silica gel chromatography (mobile phase: hexane / ethyl acetate = 1/1 (volume ratio)), and washed with hexane. Compound 2-2 was obtained (yield 44 mg).

[Example 9]
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) to give 2,6-difluoro 66.3 mg of isonicotine anilide were obtained.

２， 2,6-Difluoroisonicotinanilide (50 mg) obtained above 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) to obtain the compound of Example 5-5. (Yield 27 mg).

化合物 According to the methods of Examples 1 to 9, the compounds of Examples 1-1 to 1-260 represented by the formula (2 ″) shown in Tables 20 to 45 below were produced. Further, the compounds of Examples 2-1 to 2-5 represented by the formula (3 ′) shown in Table 46 below were produced. Further, the compounds of Example 3-1 and Example 3-2 represented by the formula (4 ″) shown in Table 47 below were produced. Further, the compounds of Examples 4-1 to 4-4 represented by the formula (5 ″) shown in Table 48 below were produced. In addition, compounds of Example 5-1 to Example 5-9 represented by the formula (6 ″) shown in Table 49 below were produced.

MS and IR of each compound represented by the formulas (2 ″), (3 ′), (4 ″), (5 ″) and (6 ″) together with the compounds obtained in Examples 1 to 9. , ¹ H-NMR data are shown in Tables 20 to 49. As a solvent for measurement of ¹ H-NMR (400 MHz, 500 MHz or 600 MHz), the compound of Example 1-8, Example 1-69, Example 1-175, Example 1-176 and Example 4-2 has a heavy solvent. Acetone, deuterated chloroform: deuterated methanol = 1: 1 was used for the compounds of Examples 1-93, and deuterated chloroform was used for the other Examples. MS was measured by the ESI-MS method. IR was measured by the KBr method.

Compounds of Examples 1-1 to 1-260 represented by the formula (2 '') are shown in Tables 20 to 45.

Table 46 shows the compounds of Examples 2-1 to 2-5 represented by the formula (3 ').

Table 47 shows the compounds of Example 3-1 and Example 3-2 represented by the formula (4 '').

Table 48 shows compounds of Examples 4-1 to 4-4 represented by the formula (5 '').

Table 49 shows compounds of Examples 5-1 to 5-9 represented by the formula (6 '').

Example 9
<Activity against cucumber downy mildew>
Acetone solution of the following example compound prepared to be 0.4 mg / mL was diluted 10-fold with water and used for the test. To the root of the cucumber (variety: four leaves) at the first leaf stage cultivated in the pot, 5 mL of the diluted solution per pot was drenched in soil. Seven days after the treatment, a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis: oomycetes) adjusted to 5 × 10 ⁴ cells / mL was sprayed and inoculated, and the humid chamber (temperature 25 ° C., humidity 100%) was sprayed for 24 hours. It was left still. Then, it was cultivated in a greenhouse, and 7 days after inoculation, the lesion area ratio of the second leaf was examined according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-5)
0: No lesion 1: Lesion area rate less than 5% 2: Lesion area rate 5% or more, less than 25% 3: Lesion area rate 25% or more, less than 50% 4: Lesion area rate 50% or more, Less than 80% 5: Lesion area rate 80% or more Severity = ((5 × number of individuals with index 5) + (4 × number of individuals with index 4) + (3 × number of individuals with index 3) + (2 × index 2) + (1 × number of individuals with index 1)) / number of surveyed individuals / 5 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The following example compounds exhibited a control value of 70 or more, and the control effect against cucumber downy mildew was confirmed.
1-117, 1-134, 1-135, 1-143, 1-218, 4-2

Example 10
<Activity against cucumber downy mildew>
An acetone solution of the following example compound prepared so as to have a concentration of 1 mg / mL was diluted 10-fold with water and subjected to a test. 1 mL of the diluent per pot was sprayed on each cucumber (variety: four leaves) at the first leaf stage cultivated in the pot. Seven days after spraying, a spore suspension of cucumber downy mildew (Pseudoperonospora cubensis: oomycetes) adjusted to 5 × 10 ⁴ cells / mL was sprayed and inoculated, and the humid chamber (temperature 25 ° C., humidity 100%) was sprayed for 24 hours. It was left still. Then, it was cultivated in a greenhouse, and 7 days after inoculation, the lesion area ratio of two leaves was examined according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-5)
0: No lesion 1: Lesion area rate less than 5% 2: Lesion area rate 5% or more, less than 25% 3: Lesion area rate 25% or more, less than 50% 4: Lesion area rate 50% or more, Less than 80% 5: Lesion area rate 80% or more Severity = ((5 × number of individuals with index 5) + (4 × number of individuals with index 4) + (3 × number of individuals with index 3) + (2 × index 2) + (1 × number of individuals with index 1)) / number of surveyed individuals / 5 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The following example compounds exhibited a control value of 70 or more, and the control effect against cucumber downy mildew was confirmed.
1-143, 1-218

Example 11
<Activity against tomato blight>
Acetone solutions prepared at 1 mg / mL for Example Compounds 1-135 and 1-168 were diluted 10-fold with water and used for the test. To the tomatoes (variety: Tiny Tim) in the first inflorescence formation stage cultivated in pots, 5 mL of the diluted solution per pot was sprayed. Seven days after spraying, a spore suspension of Phytophthora infestans (Oomycetes) adjusted to 1 × 10 ⁴ cells / mL was sprayed and inoculated, and allowed to stand overnight in a moist chamber (temperature 21 ° C., humidity 100%). did. Thereafter, the cells were cultivated in a greenhouse, and after 4 days from the inoculation, after spraying, the lesion area ratio of the developed leaves was examined according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-5)
0: No lesion 1: Lesion area rate less than 5% 2: Lesion area rate 5% or more, less than 25% 3: Lesion area rate 25% or more, less than 50% 4: Lesion area rate 50% or more, Less than 80% 5: Lesion area rate 80% or more Disease severity = ((5 × index 5 leaves) + (4 × index 4 leaves) + (3 × index 3 leaves) + (2 × index 2 leaves) + (1 × index 1 leaves)) / number of survey leaves / 5 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The following example compounds showed a control value of 50 or more, and the control effect against tomato late blight was confirmed.
1-135, 1-168

Example 12
<Activity against grape downy mildew>
For each of Example Compounds 1-135 and 1-168, a wettable powder was prepared according to Formulation Example 1, and then diluted 1000-fold with water to prepare a spray liquid. The test was performed in a field where grape downy mildew occurs naturally. The prepared spray liquid was sprayed twice at the flowering stage grape (variety: Koshu) at a liquid volume of 1 L / tree. At the third time, the prepared spray liquid was sprayed at a rate of 2 L / tree. Ten days after the third application, leaf lesions were examined according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-10)
0: No lesion 1: Lesion area rate less than 10% 2: Lesion area rate 10% or more, less than 20% 3: Lesion area rate 20% or more, less than 30% 4: Lesion area rate 30% or more, Less than 40% 5: Lesion area rate 40% or more, less than 50% 6: Lesion area rate 50% or more, less than 60% 7: Lesion area rate 60% or more, less than 70% 8: Lesion area rate 70% Above, less than 80% 9: Lesion area rate 80% or more, less than 90% 10: Lesion area rate 90% or more Severity = ((10 × index 10 leaves) + (9 × index 9 leaves) + (8 × index 8 leaves) + (7 × index 7 leaves) + (6 × index 6 leaves) + (5 × index 5 leaves) + (4 × index 4 leaves) + (3 × index 3 leaves) + (2 × index 2 leaves) + (1 × index 1 leaves)) / investigation leaves / 10 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

Example compounds 1-135 and 1-168 exhibited a control value of 65 or more, and the control effect against downy mildew was confirmed.

Example 13
<Activity against Makwauri vine disease>
An acetone solution of the following example compound prepared to be 0.5 mg / mL was diluted 10-fold with water and used for the test. 3 mL per pot of soil was drenched at the root of the cotyledon-stage makuwauri (cultivar: golden mallow) cultivated in the pot. The day after the treatment, a suspension of yeast-like cells (bud cell) of Fusarium oxysporum f. Sp melonis adjusted to 5 × 10 ⁷ cells / mL was instilled and inoculated. Then, it was cultivated in a greenhouse, and examined 28 days after inoculation according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-2)
0: No lesion 1: Yellowing of true leaves or stem 2: Death Severity = ((2 × number of individuals with index 2) + (1 × number of individuals with index 1)) / number of individuals surveyed / 2 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The following example compounds showed a control value of 60 or more, and the control effect against the scab disease of Makwauri was confirmed.
1-30, 1-41, 1-98, 1-126, 1-134, 1-135, 1-139, 1-143, 1-218, 3-1, 3-2, 4-2, 4- 4

Example 14
<Activity against Makwauri vine disease>
An acetone solution of the following example compound prepared to be 0.25 mg / mL was diluted 10-fold with water and used for the test. 3 mL per pot of soil was drenched at the base of the 1-leaf stage makuwauri (cultivar: golden mushroom) cultivated in the pot. Seven days after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a culture of Fusarium oxysporum f.sp melonis and a cultivated soil. Thereafter, the plants were cultivated in a greenhouse, and examined 28 days after planting according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-2)
0: No lesion 1: Yellowing of true leaves or stem 2: Death Severity = ((2 × number of individuals with index 2) + (1 × number of individuals with index 1)) / number of individuals surveyed / 2 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The following example compounds showed a control value of 60 or more, and the control effect against the scab disease of Makwauri was confirmed.
1-131, 1-134, 1-135, 1-136, 1-137, 1-138, 1-143, 1-144, 1-154, 1-161, 1-162, 1-163, 1- 168, 1-170, 1-173, 1-174, 1-175, 1-176, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-191, 1-198, 1-199, 1-200, 1-201, 1-203, 1-204, 1-205, 1-206, 1-207, 1-208, 1- 209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-216, 1-218, 1-219, 1-220, 1-221, 1-223, 1-224, 5-1, 5-2, 5-3, 5-4, 5-6, 5-7, 5-9

Example 15
<Activity against Makwauri vine disease>
An acetone solution of the following example compound prepared so as to have a concentration of 0.15 mg / mL was diluted 10-fold with water and subjected to a test. 0.5 mL was sprayed on the first true leaf of the 1-leaf stage makuwauri (cultivar: Golden Makowari) cultivated in a pot. Seven days after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a culture of Fusarium oxysporum f.sp melonis and a cultivated soil. Thereafter, the plants were cultivated in a greenhouse, and examined 28 days after planting according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-2)
0: No lesion 1: Yellowing of true leaves or stems 2: Withering Degree of disease = ((2 × number of individuals with index 2) + (1 × number of individuals with index 1)) / number of individuals surveyed / 2 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The following example compounds showed a control value of 60 or more, and the control effect against the scab disease of Makwauri was confirmed.
1-134, 1-218, 4-2

Example 16
<Activity against cucumber seedling blight>
An acetone solution of the following example compound prepared to be 0.5 mg / mL was diluted 10-fold with water and used for the test. At the root of the cucumber (variety: four leaves) at the cotyledon stage cultivated in the pot, 3 mL per pot was subjected to soil irrigation. One day after the treatment, the plants were planted in a mixed soil (mass ratio 1: 9) of a culture of a cucumber seedling blight fungus (Pythium ultimum var. Ultimum) and a culture medium. After that, the plants were cultivated in a greenhouse, and 15 days after planting, they were examined according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-6)
0: No disease 1: Root pot formation 80% or more 2: Root pot formation less than 80% to 50%
3: Root pot formation less than 50% to 25%
4: Root mortar formation less than 25% 5: No root mortar formation 6: Withering Degree of disease = ((6 × index 6 individuals) + (5 × index 5 individuals) + (4 × index 4 individuals) + (3 × index 3 individuals) + (2 × index 2 individuals) + (1 × index 1 individuals) / investigation individuals / 6 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The following example compounds exhibited a control value of 50 or more, and the control effect on cucumber seedling blight was confirmed.
1-189, 1-209

Example 17
<Activity against Chinese cabbage butt rot>
An acetone solution of the following example compound prepared to be 0.5 mg / mL was diluted 10-fold with water and used for the test. 3 mL per pot of the Chinese cabbage (cultivar: Muso) was irrigated with soil at the base of the three-leaf Chinese cabbage cultivated in the pot. Seven days after the treatment, the plants were planted in a mixed soil (a mass ratio of 1: 9) of a culture of a Chinese cabbage rot fungus (Rhizoctonia solani) and a culture soil. After that, the plants were cultivated in a greenhouse, and 15 days after planting, they were examined according to the following index. The disease severity was calculated based on this index, and the control value was calculated from the obtained disease severity by the following formula.
Exponent (0-6)
0: No disease 1: Root pot formation 80% or more 2: Root pot formation less than 80% to 50%
3: Root pot formation less than 50% to 25%
4: Root mortar formation less than 25% 5: No root mortar formation 6: Withering Degree of disease = ((6 × index 6 individuals) + (5 × index 5 individuals) + (4 × index 4 individuals) + (3 × index 3 individuals) + (2 × index 2 individuals) + (1 × index 1 individuals) / investigation individuals / 6 × 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

The following example compounds exhibited a control value of 50 or more, and the control effect on Chinese cabbage bottom rot was confirmed.
1-30, 1-41, 1-117, 1-189, 1-193, 1-197

Example 18
<Activity against lettuce root rot>
A wettable powder of Example Compound 1-199 was prepared according to Formulation Example 1. This wettable powder was diluted 5,000-fold with water, and 2 L of the lettuce (cultivar: Raptor) 20 days after sowing cultivated in a 220-well paper pot was irrigated and planted in a field where lettuce root rot was naturally occurring the next day. 44 days after planting, the plant was examined according to the following index to calculate the disease severity. The control value was calculated from the obtained degree of disease by the following formula.
Exponent (0-3)
0: No browning 1: Partial vascular browning 2: Browning extends around crown 3: Heavy browning or cavitation of crown, or dead (due to death of entire strain).
Disease incidence = ((3 x number of individuals with index 3) + (2 x number of individuals with index 2) + (1 x number of individuals with index 1)) / number of individuals surveyed / 3 x 100
Control value = ((degree of disease in untreated area-degree of disease in treated area) / degree of disease in untreated area) x 100

Example compound 1-199 showed a control value of 50 or more, and its control effect on lettuce root rot was confirmed.

Example 19
<Activity against cucumber homopsis root rot>
The potato sucrose liquid medium was inoculated with Phomopsis sclerotioides and cultured at 25 ° C. for 4 weeks. The obtained bacterial flora was ground by Hiscotron (Nichion Medical Science Instrument Co., Ltd.) to obtain a ground liquid. The obtained trituration liquid was mixed with soil, and this was used as homopsis-contaminated soil. An acetone solution of Example Compound 1-199 was prepared to be 1 mg / mL. This was diluted 10-fold with water, and 1/5000 volume of neoesterin was added to obtain a spray solution. A cucumber (variety: four leaves) at the cotyledon stage one week after sowing cultivated in a pot was sprayed with 0.3 mL of a spray liquid. One day after spraying, the cucumber was transplanted to homopsis-contaminated soil, cultivated in a greenhouse for 4 weeks, and then measured for plant height. When the plant height of the cucumber cultivated without transplanting to the homopsis-contaminated soil was 100, the plant height of the untreated cucumber was 66. On the other hand, the plant height of the cucumber treated with the example compound 1-199 was 97, indicating that the control effect of the example compound 1-199 against cucumber homopsis root rot was confirmed.

Example 20
The potato sucrose liquid medium was inoculated with Phomopsis sclerotioides and cultured at 25 ° C. for 4 weeks. The obtained bacterial flora was ground by Hiscotron (Nichion Medical Science Instrument Co., Ltd.) to obtain a ground liquid. The obtained trituration liquid was mixed with soil, and this was used as homopsis-contaminated soil. An acetone solution of Example Compound 1-199 was prepared to be 1 mg / mL. This was diluted 50-fold with water to obtain an irrigation solution. A cucumber (variety: four leaves) at the cotyledon stage one week after sowing cultivated in the pot was irrigated with 5 mL of an irrigation solution per pot into the soil. One day after the treatment, the cucumber was transplanted to homopsis contaminated soil, cultivated in a greenhouse for 4 weeks, and then measured for plant height. When the plant height of the cucumber cultivated without transplanting to the homopsis-contaminated soil was 100, the plant height of the untreated cucumber was 66. On the other hand, the plant height of the cucumber treated with Example Compound 1-199 was 94, thus confirming the controlling effect of Example Compound 1-199 on the root rot of cucumber homopsis.

Example 21
<Proliferation inhibitory activity against pathogenic fungi of soil disease>
The following example compounds were dissolved in DMSO to a concentration of 12.8 mg / mL. Cucumber seedling wilt fungus (Pythium ultimum), Chinese cabbage rot fungus (Rhizoctonia solani), Makwauri vine wilt fungus (Fusarium oxysporum), and homopsis root rot fungus (Phosmodios thrombosis sci.) (Kikki Seisakusho) and diluted 50 to 100 times with a potato sucrose medium to obtain a bacterial solution. 200 μL of the bacterial solution was added to 1 μL of the DMSO solution of the example compound, and the mixture was cultured at 25 ° C. for 3 days. Then, the presence or absence of inhibition of hyphal elongation was visually determined.

The following example compounds did not show inhibition of hyphal elongation.
1-198, 1-199

Example 22
The following example compounds were dissolved in DMSO to a concentration of 12.8 mg / mL. Cucumber seedling wilt fungus (Pythium ultimum) cultured in a potato sucrose liquid medium was ground with a Hiscotron (Nichion Medical Science Instruments) and diluted 50 to 100 times with a potato sucrose medium to obtain a bacterial solution. 200 μL of the bacterial solution was added to 1 μL of the DMSO solution of the example compound, and the mixture was cultured at 25 ° C. for 3 days. Then, the presence or absence of inhibition of hyphal elongation was visually determined.

The following example compounds did not show inhibition of hyphal elongation.
1-39, 1-53, 1-64, 4-2

Example 23
<Proliferation inhibitory activity against oomycetes>
The following example compounds were dissolved in DMSO to a concentration of 12.8 mg / mL. Cucumber gray blight (Phytophthora capsici) cultured in a potato sucrose liquid medium was ground with a Hiscotron (Nichion Medical Science Instrument Co., Ltd.) and diluted 50 to 100 times with a potato sucrose medium to obtain a bacterial solution. 200 μL of the bacterial solution was added to 1 μL of the DMSO solution of the example compound, and the mixture was cultured at 25 ° C. for 3 days. Then, the presence or absence of inhibition of hyphal elongation was visually determined.

The compounds of the following examples showed no inhibition of hyphal elongation.
1-39, 1-53, 1-64, 1-131, 1-134, 1-135, 1-137, 1-138, 1-139, 1-143, 1-168, 1-193, 1- 198, 1-199, 1-218, 1-220, 4-2, 4-4, 5-6

Formulation Example 1
10 parts by mass of the compound of the example, 2 parts by mass of lauryl sulfate, 2 parts by mass of polyoxyethylene alkyl ether, 3 parts by mass of ligninsulfonate, 4 parts by mass of white carbon, and 79 parts by mass of clay were mixed and pulverized to obtain a wettable powder. I got

According to the present invention, a method for controlling plant diseases can be provided. The plant disease controlling agent of the present invention has excellent resistance inducing activity and is useful for controlling plant diseases (especially diseases caused by oomycetes and soil diseases).

Claims

A plant disease controlling agent comprising a compound represented by the following formula (1) 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 any one of X 1 and X 4 Represents a fluorine atom or a trifluoromethyl group, and 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, provided that X 1 , X 2 and When any one of X 4 represents a fluorine atom, any one of the other two does not represent a hydrogen atom;
Xa is a group represented by the following formula (2), (3), (4), (5) or (6);

In the formula (2), J represents an oxygen atom or a sulfur atom,
A is
Carbon number which may be substituted by 1 to 3 groups selected from the group consisting of the following group C, thiol group, methoxycarbonyl group, ethoxycarbonyl group, methoxy group, and N-tert-butoxycarbonylamino group An alkyl group of 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 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,
Naphthyl group,
A heterocyclic group which may be substituted with 1 to 4 groups selected from the group D below, or a group represented by the following formula (2A):

In the formula (2A), X 1 , X 2 , X 3 and X 4 are the same as defined in the formula (1),
When A is a group represented by the formula (2A), Q is a divalent group represented by the formula: —O— (CH 2 ) n—O—, and a formula: —NH— (CH 2 ) n— A divalent group represented by O—, a divalent group represented by the formula: —NH— (CH 2 ) n—NH—, and a formula: —O—CH 2 —CHＣＨCH—CH 2 —O— A divalent group represented by the formula: —NH—CH 2 —CH ＝ CH—CH 2 —O—, a divalent group represented by the formula: —NH—CH 2 —CH ＝ CH—CH 2 —NH— Divalent group, cyclohexane-1,4-diyldioxy group, cyclohexane-1,4-diyldiamino group, divalent group represented by the formula: -NH- (cyclohexane-1,4-diyl) -O-, 1 , 3-phenylenediamino group, 1,4-phenylenediamino group, 1,4-phenylenedioxy group, formula: -NH- (1, - phenylene) a divalent group represented by -O-, or a divalent group represented by the following formula (2B), n represents an integer of 2-8,

In the formula (2B), Gb is an oxygen atom, a sulfur atom, or a divalent group represented by the formula: —SO 2 —,
When A is not a group represented by the formula (2A), Q represents an oxygen atom, a sulfur atom, a divalent group represented by the formula: —NH—, or a formula: —N (CH 3 ) — A divalent group,
In the formula (3), Aa represents a piperidin-1-yl group, a 1-methyl-1-H-pyrrol-2-yl group, a morpholin-4-yl group, an indoline-1-yl group, a benzoisothiazole-3 (2H) -one-1,1-dioxide-2-yl group, piperazin-1-yl group, azetidin-1-yl group, 2,5-dioxopyrrolidin-1-yl group, 3-oxoisothiazole- 2 (3H) -yl group, benzo [d] isothiazol-2 (3H) -yl group, 1,1-dioxo-3-oxobenzo [d] isothiazol-2 (3H) -yl group, 5,6- A dihydro-4H-1,3-oxazin-2-yl group, a 1H-pyrrol-2-yl group or an isoindoline-2-yl group;
In the formula (4), Qb 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
Hydrogen atom,
An alkyl group having 1 to 10 carbon atoms which may be substituted by 1 to 3 groups selected from the group consisting of the following group C, a methoxycarbonyl group and an 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,
A phenylcarbonyl group or a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D below;
In the formula (5), m represents an integer of 1 to 3, Z represents a hydrogen atom, a halogen atom or a methyl group,
In the formula (6), Ja and Jb may be the same or different and each 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;
Ad 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,
A naphthyl group or a heterocyclic group which may be substituted with 1 to 4 groups selected from the group D below;
The heterocyclic group is a group selected from the following group E,
Group C includes a halogen atom, a hydroxyl group, an amino group, a cyano group, a 5-methyl-1,3-dioxol-2-one-4-yl group, an isothiazol-5-yl group, a phenylcarbonyl group; A pyridyl group optionally substituted with 1 to 3 groups selected from groups, and a phenyl group optionally 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 dimethylamino group, an acetylamino group, a methylthio group, a methylsulfonyl group, an alkyl group having 1 to 6 carbon atoms which may be substituted by 1 to 3 halogen atoms, An alkyloxy group having 1 to 4 carbon atoms which may be substituted by 1 to 3 halogen atoms, an alkylcarbonyl group having 1 to 4 carbon atoms, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, A group consisting of a nitro group 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, benzoisothiazol-3 (2H) -one-1,1-dioxydyl group, dibenzofuranyl group, isothiazolyl group, and triazolyl group It is a group consisting of
In the formula (1), X 1, characterized in that X 2, X 3 and X 4 is a hydrogen atom or a fluorine atom, plant disease control agent according to claim 1.
3. The plant disease control agent according to claim 2, wherein in the formula (1), X 1 and X 4 represent a fluorine atom, and X 2 or X 3 is a hydrogen atom.
3. The plant disease control agent according to claim 2, wherein in the formula (1), X 1 and X 4 represent a fluorine atom, and X 2 and X 3 represent a hydrogen atom.
In the formula (1), Xa is a group represented by the formula (2), and in the formula (2), J is an oxygen atom. The plant disease controlling agent according to the above item.
In the formula (1), X a is a group represented by the formula (2), and in the formula (2), Q is a divalent group represented by the formula: —NH—. The plant disease controlling agent according to any one of claims 1 to 5.
In the formula (1), Xa is a group represented by the formula (2), and in the formula (2), Q is an oxygen atom. The plant disease controlling agent according to the above item.
In the above formula (1), Xa is a group represented by the above formula (2), and in the above formula (2), A is substituted with 1 to 3 groups selected from the group C group. An alkylcarbonyl group having 1 to 8 carbon atoms,
An alkyloxy group having 1 to 4 carbon atoms which may be substituted with 1 to 3 groups selected from the groups of the group C,
A phenylcarbonyl group which may be substituted with 1 to 4 groups selected from the group consisting of the group D, a benzyl group, a phenyl group and a phenoxy group;
A phenylsulfonyl group optionally substituted with 1 to 4 groups selected from the group D groups, or
The phenyl group which may be substituted with 1 to 5 groups selected from the group consisting of the group D, a phenoxy group and a benzyl group. The plant disease controlling agent according to the above.
In the formula (1), X a is a group represented by the formula (6), wherein the formula (6), Ja and Jb is an oxygen atom, any of claims 1 to 4, 9. The plant disease controlling agent according to claim 1.
(10) A method for controlling plant diseases, which comprises contacting the plant disease controlling agent according to any one of (1) to (9) with a plant or a seed, or containing the agent in a cultivation bed.