WO2019059161A1

WO2019059161A1 - Pyridone compound and agricultural and horticultural germicide having same as active ingredient

Info

Publication number: WO2019059161A1
Application number: PCT/JP2018/034395
Authority: WO
Inventors: 豪毅梅谷; 駿岡谷
Original assignee: 三井化学アグロ株式会社
Priority date: 2017-09-20
Filing date: 2018-09-18
Publication date: 2019-03-28
Also published as: JP7111731B2; JPWO2019059161A1

Abstract

Provided is a novel compound for controlling plant disease damage. A pyridone compound according to the present invention is a novel compound, and can control plant disease damage.

Description

Pyridone compounds and agricultural and horticultural fungicides comprising the same as an active ingredient

The present invention relates to a pyridone compound and a pesticide containing the compound as an active ingredient.

Controlling diseases of agricultural and horticultural crops plays an important role in securing stable agricultural production. Therefore, although various bactericidal agents are used, since the use of bactericidal agents for many years causes the emergence of drug-resistant bacteria, novel bactericidal agents effective against not only drug-sensitive bacteria but also drug-resistant bacteria are in great need It is done.

By the way, prior examples of 1,3,5,6-substituted 2-pyridone compounds are known. For example, 1,3,5,6-substituted 2-pyridone compounds having an aryl group or a heteroaryl group at the 3-position as a GABA alpha-2 / 3 ligand are disclosed (for example, WO 98/55480) reference). As therapeutic agents for bacterial infections, 1,3,5,6-substituted 2-pyridone compounds having a carboxyl group at the 3-position are disclosed (see, for example, European Patent No. 0308020). Furthermore, as an anti-HIV agent, a 1,3,5,6-substituted -2-pyridone compound in which 4,4-dimethylpentanoic acid is introduced at 1 position is disclosed (for example, WO 2016/012913 reference).

WO 98/55480 European Patent No. 0308020 International Publication No. 2016/12913

However, all of the uses of the compounds described in WO 98/55480, European Patent No. 0308020 and WO 2016/12913 relate to medicine, and the sterilization according to the present invention for agricultural and horticultural purposes It differs from the technical field to which the agent belongs.

An object of the present invention is to provide a novel pyridone compound which is effective as an agricultural and horticultural fungicide.

The present inventors diligently studied 1, 3, 5, 6-substituted 2-pyridone compounds and 1, 5, 6-substituted 2-pyridone compounds in order to solve the above-mentioned problems. As a result, it has been found that a novel compound group in which an alkyl group substituted with an aryl group or a heteroaryl group is introduced at the 5-position in the 2-pyridone skeleton exhibits excellent control activity against plant diseases. The present invention has been completed.

That is, the present invention is as follows.

[1]
Formula (1)

[Wherein, R 1 is
Hydroxyl group,
Cyano group,
A C1 to C6 alkyl group optionally substituted with a substituent A,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent A,
A C2-C6 alkenyl group which may be optionally substituted by a substituent A,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent A,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent A,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent A,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent A,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent A,
A C3-C6 haloalkynyloxy group,
Or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 And R.sup.A and R.sup.b, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl or azocanyl group. Represent;
R2 is
Hydrogen atom,
Nitro group,
Halogen atom,
A C1 to C6 alkyl group optionally substituted with a substituent A,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent A,
A C2-C6 alkenyl group which may be optionally substituted by a substituent A,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent A,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent A,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent A,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent A,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent A,
A C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO2),
Or RdC (= O) — (wherein, Rd represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent B). Represents
X represents an oxygen atom or a sulfur atom;
Y is
An aryl group which may be optionally substituted 0 to 7 as R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently),
Or a heteroaryl group which may be optionally substituted 0 to 4 with R 3 (provided that R 3 s each having 2 or more substituents are each independently);
R3 is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent C,
A C2-C6 alkenyl group which may be optionally substituted by a substituent C,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent C,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent C,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
RaR b N-(wherein, R a and R b are as defined above),
Rc-L- (wherein Rc and L are as defined above),
Rx1C (= O)-(wherein, Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy A group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above),
Or Rx1C (= O) O— (wherein, Rx1 is as defined above);
Z is
An aryl group which may be optionally substituted 0 to 7 as R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
Or a heterocyclic group which may be optionally substituted 0 to 6 with R 4 (provided that each is independently R 2 in the case of 2 or more substituents R 4);
R4 is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent C,
A C2-C6 alkenyl group which may be optionally substituted by a substituent C,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent C,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent C,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
An aryl group which may be optionally substituted by a substituent D,
A heteroaryl group which may be optionally substituted by a substituent D,
An aryloxy group which may be optionally substituted by a substituent D,
A heteroaryloxy group which may be optionally substituted by a substituent D,
An aralkyloxy group which may be optionally substituted by a substituent D,
RaR b N-(wherein, R a and R b are as defined above),
Rc-L- (wherein Rc and L are as defined above),
Rx1C (= O)-(where Rx1 is the same as the above),
Rx1C (= O) O- (wherein, Rx1 is as defined above),
Or Rx2C (= O) N (Rx3)-(wherein, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cyclo An alkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is A hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.
W is
A C1 to C6 alkylene group which may be optionally substituted 0 to 2 with R 5 (wherein each of R 5 s is independently substituted);
R5 is
Hydroxyl group,
Cyano group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent C,
A C2-C6 alkenyl group which may be optionally substituted by a substituent C,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent C,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent C,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc and L are as defined above),
Or Rx1C (= O) O— (wherein, Rx1 is as defined above);
And, the substituent A is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, RaRbN- (where, Ra And Rb is as defined above) and Rc-L- (wherein Rc and L are as defined above) and at least one selected from the group consisting of
The substituent B is at least one selected from the group consisting of a cyano group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group and a C3 to C8 cycloalkoxy group;
The substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN -(Wherein, Ra and Rb are as defined above), Rc-L- (wherein, Rc and L are as defined above), Rx1C (= O)-(wherein, Rx1 At least one selected from the group consisting of the groups having the same meanings as described above) and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D includes a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, C1 to C6. It is at least one selected from the group consisting of a C6 alkoxy group, a C1 to C6 haloalkoxy group, and a C3 to C8 cycloalkoxy group. Or a salt thereof.

[2]
Y is
A phenyl group which may be optionally substituted 0 to 5 as R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently),
A pyridyl group which may be optionally substituted 0 to 4 with R 3 (provided that R 3 s each having 2 or more substituents are independent of each other),
A pyridazinyl group, a pyrimidinyl group or a pyrazinyl group which may be optionally substituted 0 to 3 by R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently),
A triazinyl group which may be optionally substituted 0 to 2 as R 3 (however, in the case of disubstituted R 3, each is independent of each other),
Or a tetrazinyl group which may be optionally substituted by R 3;
Z is
A phenyl group which may be optionally substituted 0 to 5 with R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
A naphthyl group which may be optionally substituted 0 to 7 with R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
A pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group (however, in the case of R4 having two or more substituents, they are each independently.
Thienyl group which may be optionally substituted by 0 to 4 R 4, thiazolyl group, isothiazolyl group, thiadiazolyl group, or thiatriazolyl group (However, in the case of R 4 having two or more substituents, they are each independently.),
A pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, or a pentazolyl group (however, in the case of R4 having two or more substituents, they are each independently independent of each other)
Furyl, oxazolyl, isoxazolyl, oxadiazolyl or oxatriazolyl (which may be independently substituted in the case of R4 having 2 or more substituents) which may be optionally substituted by 0 to 3 R 4;
Indolyl, isoindolyl, indazolyl, benzimidazolyl, or benzotriazolyl groups which may be optionally substituted 0 to 6 by R 4 (however, in the case of R 4 having 2 or more substituents, they are each independently),
Benzofuryl group, isobenzofuryl group, benzoxazolyl group, benzoisoxazolyl group, or benzooxadiazolyl group (however, in the case of R4 having two or more substituents, each of which may be optionally substituted 0 to 5 with R 4 be independent.),
A benzothienyl group, a benzothiazolyl group, a benzoisothiazolyl group, or a benzothiadiazolyl group (however, in the case of R4 having 2 or more substituents, they are each independently independent) which may be optionally substituted 0 to 5 with R 4;
Indolizinyl group which may be optionally substituted 0 to 6 by R 4, imidazopyridyl group, pyrazolo pyridyl group, or triazolo pyridyl group (However, in the case of R 4 having 2 or more substituents, they are each independently.),
A pyrrolopyrimidinyl group which may be optionally substituted by 0 to 4 R 4, imidazopyrimidinyl group, pyrazolopyrimidinyl group, triazolopyrimidinyl group, pyrrolopyrazinyl group, imidazopyrazinyl group, pyrazolopyrazinyl group, or triazolopyrazinyl group Group (but in the case of R 4 with 2 or more substituents, each is independent),
A quinolyl group, an isoquinolyl group, a cinolyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, or a naphthyridinyl group which may be optionally substituted 0 to 6 with R 4 (however, in the case of R4 having 2 or more substituents, they are each independently). ,
Or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms,
The compound or its salt as described in [1].

[3]
R1 is
A C1 to C6 alkyl group optionally substituted with a substituent A,
C1 to C6 haloalkyl group,
A C2-C6 alkenyl group which may be optionally substituted by a substituent A,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent A,
Or C2 to C6 haloalkynyl group;
R2 is
Hydrogen atom,
Halogen atom,
A C1 to C6 alkyl group optionally substituted with a substituent A,
C1 to C6 haloalkyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent A,
A C1 to C6 haloalkoxy group,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO2),
Or RdC (= O) — (wherein, Rd represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent B). Represents
Y is
A phenyl group which may be optionally substituted 0 to 5 as R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently),
Or a pyridyl group which may be optionally substituted 0 to 4 with R 3 (provided that R 3 s each having 2 or more substituents are independently of each other);
R3 is
Hydroxyl group,
Cyano group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
Or Rx1C (= O) O— (wherein, Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1-C6 Or an alkoxy group of C1 to C6, a haloalkoxy group of C1 to C6, a cycloalkoxy group of C3 to C8, or RaRbN- (wherein Ra and Rb are each independently, and optionally substituted by a hydrogen atom or a substituent B Represents a good C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which it is attached is an aziridinyl group, azetidinyl group, pyrrolidinyl group A group, piperidinyl group, homopiperidinyl group, or those forming an azocanyl group).
Z is
A phenyl group which may be optionally substituted 0 to 5 with R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
A pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group (however, in the case of R4 having two or more substituents, they are each independently.
Thienyl group which may be optionally substituted by 0 to 4 R 4, thiazolyl group, isothiazolyl group, thiadiazolyl group, or thiatriazolyl group (However, in the case of R 4 having two or more substituents, they are each independently.),
A pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, or a pentazolyl group which may be optionally substituted 0 to 4 by R 4 (however, in the case of R 4 having two or more substituents, they are each independently).
Or R4 represents a furyl group which may be optionally substituted by 0 to 3, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, or an oxatriazolyl group (provided that they are each independently in the case of R4 having 2 or more substituents). ;
R4 is
Hydroxyl group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C2-C6 alkenyl group which may be optionally substituted by a substituent C,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent C,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc and L are as defined above),
Rx1C (= O)-(where Rx1 is the same as the above),
Or Rx1C (= O) O— (wherein, Rx1 is as defined above);
R5 is
Hydroxyl group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
Or Rx1C (= O) O— (wherein, Rx1 is as defined above),
The compound or its salt as described in [2].

[4]
R1 is
A C1 to C6 alkyl group optionally substituted with a substituent A,
Or a C1 to C6 haloalkyl group;
R2 is
Hydrogen atom,
Halogen atom,
A C1 to C6 alkyl group optionally substituted with a substituent A,
Or a C1-C6 alkoxy group optionally substituted by a substituent A;
Y is
Represents a phenyl group which may be optionally substituted 0 to 5 with R 3 (provided that R 3 is 2 or more, each of which is independently of each other);
R3 is
Hydroxyl group,
Cyano group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
Or Rx1C (= O) O— (wherein, Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1-C6 Or an alkoxy group of C1 to C6, a haloalkoxy group of C1 to C6, a cycloalkoxy group of C3 to C8, or RaRbN- (wherein Ra and Rb are each independently, and optionally substituted by a hydrogen atom or a substituent B Represents a good C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which it is attached is an aziridinyl group, azetidinyl group, pyrrolidinyl group A group, piperidinyl group, homopiperidinyl group, or those forming an azocanyl group).
Z is
A phenyl group which may be optionally substituted 0 to 5 with R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
A pyrazolyl group, an imidazolyl group, or a triazolyl group which may be optionally substituted 0 to 4 with R 4 (however, in the case of R 4 having 2 or more substituents, they are each independently).
Or an oxazolyl group which may be optionally substituted 0 to 3 with R 4, or an isoxazolyl group (provided that R 4 s each having 2 or more substituents each are independently of each other);
R4 is
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
Or a C1 to C6 alkoxy group optionally substituted by a substituent C;
W is
A methylene group which may be optionally substituted by 0 to 2 as R 5, or an ethylene group (provided that they are each independently in the case of R 5 as di-substituted);
R5 is
Hydroxyl group,
Halogen atom,
Or a C1 to C6 alkoxy group optionally substituted by a substituent C,
The compound as described in [3], or a salt thereof.

[5]
An agricultural and horticultural pest control agent comprising the compound according to [1] or a salt thereof as an active ingredient.

[6]
An agricultural and horticultural fungicide containing the compound according to [1] or a salt thereof as an active ingredient.

[7]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent described in [5] to plants, plant seeds, or soil where plants are grown.

[8]
A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicides described in [6] to plants, plant seeds, or soil where plants are grown.

According to the present invention, a novel compound which is effective as an agricultural and horticultural fungicide can be provided.

Hereinafter, the best mode for carrying out the present invention will be described in detail.

Unless otherwise stated, each term used in the claims and the specification is according to the definition generally used in the relevant technical field.

Abbreviations used herein are described below.
DMF: N, N- dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Ph: phenyl group, c: cyclo, i: iso, sec: secondary, t: tertiary, = : A double bond, ≡: represents a triple bond. In the columns of the table, for Pr, when there is no prefix, it means normal.

The definitions of the terms used in the present specification are described below.
The description Cx to Cy represents having x to y carbon atoms.

The term "optionally substituted" means substituted or unsubstituted. When this term is used, when the number of substituents is not specified, the number of substituents is 1.

The C1 to C6 alkyl group may be linear or branched and may be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl Group, 1-methylbutyl group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl group, 1,2-dimethylpropyl group, hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3- Dimethylbutyl, 2-ethylbutyl, 1-isopropylpropyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, etc. And the like.

The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.
The C1 to C6 haloalkyl group means one in which a hydrogen atom in the above C1 to C6 alkyl group is optionally substituted by one or two or more halogen atoms. When substituted by two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution thereof is not particularly limited as long as it can be present as a substituent. As specific examples of C1 to C6 haloalkyl groups, monofluoromethyl group, difluoromethyl group, trifluoromethyl group, monochloromethyl group, monobromomethyl group, monoiodomethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, 1 -Fluoroethyl group, 2-fluoroethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group , Pentafluoroethyl group, 2,2,2-trichloroethyl group, 3,3-difluoropropyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 2,2,2 -Trifluoro-1- (trifluoromethyl) ethyl group, nonafluorobutyl group, nonafluoro sec- butyl group, 3,3,4,4,5,5,5-heptafluoro-pentyl group, undecyl decafluoropentyl, tridecafluorohexyl group, and the like.

Examples of the C3 to C8 cycloalkyl group include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group.

The C2-C6 alkenyl group represents an unsaturated hydrocarbon group which has one or more double bonds and is linear or branched. In addition, when there is a geometric isomer, it is particularly limited as long as it is a range of the designated carbon number only in either one of E form or Z form or a mixture of any ratio of E form and Z form. There is nothing to do. Specific examples of C2-C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-1-propenyl, 1-pentenyl , 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 2-methyl-1-butenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 And -hexenyl group, 5-hexenyl group, 4-methyl-3-pentenyl group, 3-methyl-2-pentenyl group and the like.

The C2 to C6 haloalkenyl group means one in which a hydrogen atom in the above C2 to C6 alkenyl group is optionally substituted by one or two or more halogen atoms. When substituted by two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution thereof is not particularly limited as long as it can be present as a substituent. Specific examples of C2 to C6 haloalkenyl groups include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 3, Examples thereof include 3-dichloroallyl group, 4,4-difluoro-3-butenyl group, 5,5-difluoro-4-pentenyl group, 6,6-difluoro-5-hexenyl group and the like.

The C2-C6 alkynyl group means an unsaturated hydrocarbon group which has one or more triple bonds and is linear or branched. Specific examples of the C2-C6 alkynyl group include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group , 4-pentynyl group, 1,1-dimethyl-2-propynyl group, 1-hexynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group and the like.

The C2 to C6 haloalkynyl group means one in which a hydrogen atom in the above C2 to C6 alkynyl group is optionally substituted by one or two or more halogen atoms. When substituted by two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution thereof is not particularly limited as long as it can be present as a substituent. Specific examples of C2 to C6 haloalkynyl groups are 2-fluoroethynyl group, 2-chloroethynyl group, 2-bromoethynyl group, 2-iodoethynyl group, 3,3-difluoro-1-propynyl group, 3-chloro -3,3-Difluoro-1-propynyl group, 3-bromo-3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1-propynyl group, 4,4-difluoro-1-butynyl group Group, 4,4-difluoro-2-butynyl group, 4-chloro-4,4-difluoro-1-butynyl group, 4-chloro-4,4-difluoro-2-butynyl group, 4-bromo-4,4 -Difluoro-1-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, 4,4,4-trifluoro-2-butynyl group , 5 5-difluoro-3-pentynyl group, 5-chloro-5,5-difluoro-3-pentynyl group, 5-bromo-5,5-difluoro-3-pentynyl group, 5,5,5-trifluoro-3- Pentynyl group, 6,6-difluoro-4-hexynyl group, 6-chloro-6,6-difluoro-4-hexynyl group, 6-bromo-6,6-difluoro-4-hexynyl group, 6,6,6- The trifluoro-4-hexynyl group etc. are mentioned.

The C1 to C6 alkoxy group represents one in which the above C1 to C6 alkyl group is bonded via an oxygen atom. Specific examples of the C1 to C6 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a t-butoxy group, a pentyloxy group and an isopentyloxy group. Group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropyloxy group, hexyloxy group, 4-methylpentyloxy group, 3-methylpentyloxy group, 2-methylpentyloxy group, 1-methylpentyloxy group , 3,3-dimethylbutoxy, 2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,3-dimethylbutoxy, 2-ethyl butoxy and the like.

The C1 to C6 haloalkoxy group means one in which a hydrogen atom in the above C1 to C6 alkoxy group is optionally substituted by one or two or more halogen atoms. When substituted by two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution thereof is not particularly limited as long as it can be present as a substituent. Specific examples of C1 to C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2 -Trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,2-trichloroethoxy group, 3,3-difluoropropyloxy group, 3,3,3-tributyl group Fluoropropyloxy group, heptafluoropropyloxy group, heptafluoroisopropyloxy group, 2,2,2-trifluoro-1- (trifluoromethyl) -ethoxy group, nonafluorobutoxy group, nonafluoro-sec-butoxy group, 3 3,4,4,5,5,5-heptafluoropentyloxy group Undecafluoro pentyloxy group, tridecafluorohexyl group, and the like.

The C3 to C8 cycloalkoxy group means that the above C3 to C8 cycloalkyl group is bonded via an oxygen atom. Specific examples of the C3 to C8 cycloalkoxy group include cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group and the like.

The C 2 -C 6 alkenyloxy group represents one in which the above C 2 -C 6 alkenyl group is bonded via an oxygen atom. In addition, when there is a geometric isomer, it is particularly limited as long as it is a range of the designated carbon number, and it is a mixture of only one of either the E form or the Z form or an arbitrary ratio of the E form and the Z form. There is nothing to do. Specific examples of the C 2 -C 6 alkenyloxy group include vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 2-methyl-1-propenyloxy group, 1 -Pentenyl oxy group, 2-pentenyl oxy group, 3-pentenyl oxy group, 4-pentenyl oxy group, 2-methyl-1-butenyloxy group, 3-methyl-2- butenyloxy group, 1-hexenyl oxy group, 2-hexenyl Examples thereof include an oxy group, a 3-hexenyl oxy group, a 4-hexenyl oxy group, a 5-hexenyl oxy group, a 4-methyl-3-pentenyl oxy group, and a 3-methyl-2-pentenyl oxy group.

The C2 to C6 haloalkenyloxy group means one in which a hydrogen atom in the above C2 to C6 alkenyloxy group is optionally substituted by one or two or more halogen atoms. When substituted by two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution thereof is not particularly limited as long as it can be present as a substituent. Specific examples of C2 to C6 haloalkenyloxy groups include 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 2,2-dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoro Allyloxy, 3,3-dichloroallyloxy, 4,4-difluoro-3-butenyloxy, 5,5-difluoro-4-pentenyloxy, 6,6-difluoro-5-hexenyloxy and the like Be

The C 3 -C 6 alkynyloxy group represents one of the C 2 -C 6 alkynyl groups described above in which a C 3 -C 6 alkynyl group is bonded via an oxygen atom. Specific examples of the C3-C6 alkynyloxy group include propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1, 1 And -dimethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group and the like.

The C3 to C6 haloalkynyloxy group means one in which a hydrogen atom in the C3 to C6 alkynyloxy group is optionally substituted by one or two or more halogen atoms. When substituted by two or more halogen atoms, those halogen atoms may be the same or different, and the number of substitution thereof is not particularly limited as long as it can be present as a substituent. Specific examples of the C3 to C6 haloalkynyloxy group include a 1,1-difluoro-2-propynyloxy group, a 4,4-difluoro-2-butynyloxy group, and a 4-chloro-4,4-difluoro-2-butynyloxy group. , 4-bromo-4,4-difluoro-2-butynyloxy group, 4,4,4-trifluoro-2-butynyloxy group, 5,5-difluoro-3-pentynyloxy group, 5-chloro-5,5 -Difluoro-3-pentynyloxy group, 5-bromo-5,5-difluoro-3-pentynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 6,6-difluoro-4 -Hexynyloxy group, 6-chloro-6,6-difluoro-4-hexynyloxy group, 6-bromo-6,6-difluoro-4-hexynyloxy group, 6,6,6- Trifluoroacetic 4- hexynyloxy group.

The aryl group represents a cyclic aromatic substituent composed of a hydrogen atom and a carbon atom. A phenyl group, a naphthyl group, etc. are mentioned as a specific example of an aryl group.

The heteroaryl group is a cyclic aromatic substituent selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom and containing at least one hetero atom as a constituent atom of the ring. Specific examples of the heteroaryl group are pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, Triazolyl group, tetrazolyl group, pentazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, oxatriazolyl group, indolyl group, isoindolyl group, indazolyl group, benzoimidazolyl group, benzotriazolyl group, benzofuryl group, isobenzo Furyl group, benzoxazolyl group, benzoisoxazolyl group, benzooxadiazolyl group, benzothienyl group, benzothiazolyl group, benzoisothiazolyl group, benzothiadiazolyl group, Anddriazolyl group, imidazo pyridyl group, pyrazolo pyridyl group, triazolo pyridyl group, pyrrolo pyrimidinyl group, imidazo pyrimidinyl group, pyrazolo pyrimidinyl group, triazolo pyrimidinyl group, pyrrolo pyrazinyl group, imidazo pyrazinyl group, pyrazolo pyrazinyl group And triazolopyrazinyl group, quinolyl group, isoquinolyl group, cinolyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, naphthyridinyl group and the like.

The heterocyclic group is a cyclic aromatic substituent or a cyclic aliphatic substituent selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom and containing at least one hetero atom as a constituent atom of the ring. Specific examples of the cyclic aromatic substituent are the same as those exemplified for the above-mentioned heteroaryl group. Specific examples of the cyclic aliphatic substituent include 1,2-epoxyethanyl group, oxetanyl group, oxoranyl group, oxanyl group, 1,3-dioxolanyl group, 1,3-dioxanyl group, 1,4-dioxanyl group , Thiiranyl group, thietanyl group, thioranyl group, thianyl group, aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, azocanyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, 1,3-oxathianyl group, 1,4 -Oxatianil group etc. are mentioned.

The aryloxy group means that the above-mentioned aryl group is bonded via an oxygen atom. A phenoxy group, a naphthyloxy group, etc. are mentioned as a specific example of an aryloxy group.

The heteroaryloxy group means that the above-mentioned heteroaryl group is bonded via an oxygen atom. Specific examples of the heteroaryloxy group include pyridyloxy group, pyridazinyloxy group, pyrimidinyloxy group, pyrazinyloxy group, triazinyloxy group, tetradinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy Group, thiadiazolyloxy group, thiatriazolyloxy group, pyrrolyloxy group, pyrazolyloxy group, imidazolyloxy group, triazolyloxy group, tetrazolyloxy group, pentazolyloxy group, furyloxy group, oxazolyl Oxy group, isoxazolyloxy group, oxadiazolyloxy group, oxa triazolyloxy group, indolyloxy group, isoindolyloxy group, indazolyloxy group, benzoimidazolyloxy group, benzotriazolyloxy group , Benzofuryloxy group, iso Nzofulyloxy group, benzoxazolyloxy group, benzoisoxazolyloxy group, benzooxadiazolyloxy group, benzothienyloxy group, benzothiazolyloxy group, benzoisothiazolyloxy group, benzothiadiazolyloxy group , Indolizinyloxy group, imidazopyridyloxy group, pyrazolo pyridyloxy group, triazolo pyridyloxy group, pyrrolopyrimidinyloxy group, imidazopyrimidinyloxy group, pyrazolopyrimidinyloxy group, triazolopyrimidinyloxy group, pyrrolopyrazinyl group Oxy group, imidazopyrazinyloxy group, pyrazolopyrazinyloxy group, triazolopyrazinyloxy group, quinolyloxy group, isoquinolyloxy group, sinoryloxy group, phthalazinyloxy group, quinoxalinyloxy group , Kina Riniruokishi group, naphthyridone isoxazolidinyl group, and the like.

The C1 to C6 aralkyl group represents one in which a hydrogen atom in a C1 to C6 alkyl group is substituted by the above-mentioned aryl group. Specific examples of the C1 to C6 aralkyl group include benzyl, phenethyl, phenylpropyl, phenylbutyl, phenylpentyl, phenylhexyl, naphthalenylmethyl, naphthalenylethyl and naphthalenylpropyl groups. , Naphthalenylbutyl group, naphthalenylpentyl group, naphthalenylhexyl group and the like.

The C1-C6 heteroaralkyl group means one in which a hydrogen atom in the C1-C6 alkyl group is substituted with the above-mentioned heteroaryl group. As specific examples of C1 to C6 heteroaralkyl groups, pyridylmethyl group, pyridylethyl group, pyridylpropyl group, pyridylbutyl group, pyridylpentyl group, pyridylhexyl group, pyridazinylmethyl group, pyridazinylethyl group, Pyridazinylpropyl, pyridazinylbutyl, pyridazinylpentyl, pyridazinylhexyl, pyrimidinylmethyl, pyrimidinylethyl, pyrimidinylpropyl, pyrimidinylbutyl, pyrimidinylpentyl, pyrimidinylhexyl Pyrazinylmethyl group, pyrazinylethyl group, pyrazinylpropyl group, pyrazinylbutyl group, pyrazinylpentyl group, pyrazinylhexyl group, triazinylmethyl group, triazinylethyl group, triazinylpropyl group, triazinylbutyl group , Triazinilpe Tyl, triazinylhexyl, tetrazinylmethyl, tetrazinylethyl, tetrazinylpropyl, tetrazinylbutyl, tetrazinylpentyl, tetrazinylhexyl, thienylmethyl, thienylethyl , Thienylpropyl, thienylbutyl, thienylpentyl, thienylhexyl, thiazolylmethyl, thiazolylethyl, thiazolylpropyl, thiazolylbutyl, thiazolylpentyl, thiazolylhexyl, isothiazolylmethyl, isothiol Azolylethyl group, isothiazolylpropyl group, isothiazolylbutyl group, isothiazolylpentyl group, isothiazolylhexyl group, thiadiazolylmethyl group, thiadiazolylethyl group, thiadiazolylpropyl group, thiadiazolyl group Butyl group, thiadi Zoryl pentyl group, thiadiazolyl hexyl group, thia triazolyl methyl group, thia triazolyl ethyl group, thia triazolyl propyl group, thia triazolyl butyl group, thia triazolyl pentyl group, thia triazolyl hexyl group, Pyrrolyl methyl group, pyrrolyl ethyl group, pyrrolyl propyl group, pyrrolyl butyl group, pyrrolyl pentyl group, pyrrolyl hexyl group, pyrazolyl methyl group, pyrazolyl ethyl group, pyrazolyl propyl group, pyrazolyl butyl group, pyrazolyl pentyl group, pyrazolyl hexyl group, imidazolyl methyl group , Imidazolyl ethyl group, imidazolyl propyl group, imidazolyl butyl group, imidazolyl pentyl group, imidazolyl hexyl group, triazolyl methyl group, triazolyl ethyl group, triazolyl propyl group, triazolyl aryl group Group, triazolylpentyl group, triazolylhexyl group, tetrazolylmethyl group, tetrazolylethyl group, tetrazolylpropyl group, tetrazolylbutyl group, tetrazolylpentyl group, tetrazolylhexyl group, penta Zorylmethyl, pentazolylethyl, pentazolylpropyl, pentazolylbutyl, pentazolylpentyl, pentazolylhexyl, furylmethyl, furylethyl, furylpropyl, furylbutyl, furyl Pentyl, furylhexyl, oxazolylmethyl, oxazolylethyl, oxazolylpropyl, oxazolylbutyl, oxazolylpentyl, oxazolylhexyl, isoxazolylmethyl, iso Xazolylethyl group, isoxazolylpropyl group, isoxazolylbutyl , Isoxazolyl pentyl group, isoxazolyl hexyl group, oxadiazolyl methyl group, oxadiazolyl ethyl group, oxadiazolyl propyl group, oxadiazolyl butyl group, oxadiazolyl pentyl group, oxadiazolyl hexyl group, Oxatriazolyl methyl group, Oxa triazolyl ethyl group, Oxa triazolyl propyl group, Oxa triazolyl butyl group, Oxa triazolyl pentyl group, Oxa triazolyl hexyl group, Indolyl methyl group, Indolyl ethyl group , Indolylpropyl, indolylbutyl, indolylpentyl, indolylhexyl, isoindolylmethyl, isoindolylethyl, isoindolylpropyl, isoindolylbutyl, isoindolylpentyl, Isoindolylhexyl group Indazolyl methyl group, indazolyl ethyl group, indazolyl propyl group, indazolyl butyl group, indazolyl pentyl group, indazolyl pentyl group, benzoimidazolyl methyl group, benzimidazolyl ethyl group, benzimidazolyl propyl group, benzimidazolyl butyl group , Benzoimidazolyl pentyl group, benzoimidazolyl hexyl group, benzotriazolyl methyl group, benzotriazolyl ethyl group, benzotriazolyl propyl group, benzotriazolyl butyl group, benzotriazolyl pentyl group, benzotriazolyl hexyl group, Benzofurylmethyl group, benzofurylethyl group, benzofurylpropyl group, benzofurylbutyl group, benzofurylpentyl group, benzofurylhexyl group, isobenzofurylmethyl group, isobenzofuryl Ethyl group, isobenzofurylpropyl group, isobenzofurylbutyl group, isobenzofurylpentyl group, isobenzofurylhexyl group, benzoxazolylmethyl group, benzoxazolylethyl group, benzoxazolylpropyl group, benzooxa Zorylbutyl, benzoxazolylpentyl, benzoxazolylhexyl, benzoisoxazolylmethyl, benzoisoxazolylethyl, benzoisoxazolylpropyl, benzoisoxazolyl butyl, Benzoisoxazolyl pentyl group, Benzoisoxazolyl hexyl group, Benzo oxadiazolyl methyl group, Benzo oxadiazolyl ethyl group, Benzo oxadiazolyl propyl group, Benzo oxadiazolyl butyl group, Benzo oxadiazolyl pentyl group, Benzo Oki Diazolylhexyl group, benzothienylmethyl group, benzothienylethyl group, benzothienylpropyl group, benzothienylbutyl group, benzothienylpentyl group, benzothienylhexyl group, benzothiazolylmethyl group, benzothiazolylethyl group, benzo Thiazolylpropyl group, benzothiazolylbutyl group, benzothiazolylpentyl group, benzothiazolylhexyl group, benzoisothiazolyl methyl group, benzoisothiazolyl ethyl group, benzoisothiazolyl propyl group, benzoisothiazole group Rylbutyl, benzoisothiazolylpentyl, benzoisothiazolylhexyl, benzothiadiazolylmethyl, benzothiadiazolylethyl, benzothiadiazolylpropyl, benzothiadiazolylbutyl, benzothiadiazolyl Rupe Ethyl, benzothiadiazolylhexyl, indolizinylmethyl, indolizinylethyl, indolizinylpropyl, indolizinylbutyl, indolizinylpentyl, indolizinylhexyl, imidazopyridylmethyl, Imidazo pyridylethyl group, imidazo pyridylpropyl group, imidazo pyridyl butyl group, imidazo pyridyl pentyl group, imidazo pyridyl hexyl group, pyrazolo pyridyl methyl group, pyrazolo pyridyl ethyl group, pyrazolo pyridyl propyl group, pyrazolo pyridyl butyl group, pyrazolo pyridyl butyl group Zoro pyridyl pentyl group, pyrazolo pyridyl hexyl group, triazolo pyridyl methyl group, triazolo pyridyl ethyl group, triazolo pyridyl propyl group, triazolo pyridyl butyl group, triazolo pyridyl pentyl group, triazo Ropyridylhexyl, pyrrolopyrimidinylmethyl, pyrrolopyrimidinylethyl, pyrrolopyrimidinylpropyl, pyrrolopyrimidinylbutyl, pyrrolopyrimidinylpentyl, pyrrolopyrimidinylhexyl, imidazopyrimidinylmethyl, imidazopyrimidinylethyl, imidazopyrimidinyl, Imidazopyrimidinyl butyl group, imidazo pyrimidinyl pentyl group, imidazo pyrimidinyl hexyl group, pyrazolo pyrimidinyl methyl group, pyrazolo pyrimidinyl ethyl group, pyrazolo pyrimidinyl propyl group, pyrazolo pyrimidinyl butyl group, pyrazolo pyrimidinyl pentyl group, pyrazolo pyrimidinyl hexyl group , Triazolopyrimidinylmethyl group, triazolopyrimidinylethyl group, triazolopyrimidinylpropyl group, Triazolopyrimidinylbutyl group, triazolopyrimidinylpentyl group, triazolopyrimidinylhexyl group, pyrrolopyrazinylmethyl group, pyrrolopyrazinylethyl group, pyrrolopyrazinylpropyl group, pyrrolopyrazinylbutyl group, pyrrolopyrazinyl group Pentyl, pyrrolopyrazinylhexyl, imidazopyrazinylmethyl, imidazopyrazinylethyl, imidazopyrazinylpropyl, imidazopyrazinylbutyl, imidazopyrazinylpentyl, imidazopyrazinyl, Pyrazolo pyrazinyl methyl group, pyrazolo pyrazinyl ethyl group, pyrazolo pyrazinyl propyl group, pyrazolo pyrazinyl butyl group, pyrazolo pyrazinyl pentyl group, pyrazolo pyrazinyl hexyl group, triazolopy Ladinylmethyl group, triazolopyrazinylethyl , Triazolopyrazinylpropyl group, triazolopyrazinylbutyl group, triazolopyrazinylpentyl group, triazolopyrazinylhexyl group, quinolylmethyl group, quinolylethyl group, quinolylpropyl group, quinolylbutyl group, quinolylpentyl group , Quinolylhexyl group, isoquinolylmethyl group, isoquinolylethyl group, isoquinolylpropyl group, isoquinolylbutyl group, isoquinolylpentyl group, isoquinolylhexyl group, sinolylmethyl group, sinolylethyl group, sinolyl A propyl group, a cinolyl butyl group, a cinolyl pentyl group, a cinolyl hexyl group, a phthalazinyl methyl group, a phthalazinyl ethyl group, a phthalazinyl propyl group, a phthalazinyl butyl group, a phthalazinyl pentyl group, a phthalazinyl hexyl group, quinoxa Rylmethyl group, quinoxalyl Ethyl group, quinoxalyl propyl group, quinoxalyl butyl group, quinoxalyl pentyl group, quinoxalyl hexyl group, quinazolinyl methyl group, quinazolinyl ethyl group, quinazolinyl propyl group, quinazolinyl butyl group , Quinazolinylpentyl, quinazolinylhexyl, naphthyridinylmethyl, naphthyridinylethyl, naphthyridinylpropyl, naphthyridinylbutyl, naphthyridinylpentyl, naphthyridinylhexyl and the like Be

The aralkyloxy group means that the above-mentioned aralkyl group is bonded via an oxygen atom. Specific examples of the aralkyloxy group include benzyloxy group, phenethyloxy group, phenylpropyloxy group, phenylbutoxy group, phenylpentyloxy group, phenylhexyloxy group, naphthalenyl methoxy group, naphthalenyl ethoxy group, naphthalenyl A propoxy group, naphthalenyl butoxy group, naphthalenyl pentyloxy group, naphthalenyl hexyl oxy group etc. are mentioned.

The C1 to C6 alkylene group is linear and includes methylene, ethylene, propylene, butylene, pentylene and hexylene groups.

Specific examples of the 3- to 6-membered ring group containing 1 to 2 oxygen atoms include a 1,2-epoxyethanyl group, an oxetanyl group, an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, and a 1,3-dioxolanyl group. Dioxanyl group, 1,4-dioxanyl group and the like can be mentioned.

The C2 to C6 alkoxyalkoxy group is a group in which a hydrogen atom in a C1 to C5 alkoxy group among the above C1 to C6 alkoxy groups is optionally substituted by one or more C1 to C5 alkoxy groups Represents The total number of carbons is not particularly limited as long as it is within the specified number of carbons. Specific examples of the C 2 -C 6 alkoxyalkoxy group include methoxymethoxy, ethoxymethoxy, propyloxymethoxy, isopropyloxymethoxy, methoxyethoxy, ethoxyethoxy, propyloxyethoxy, isopropyloxyethoxy, methoxypropyl Examples include oxy, ethoxypropyloxy, propyloxypropyloxy, isopropyloxypropyloxy and the like.

The pyridone compound of the present invention includes a compound represented by the following formula (1) and a salt thereof.

Hereinafter, Formula (1) is demonstrated.

R 1 in the formula (1) is a hydroxyl group, a cyano group, a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, C3 optionally substituted with substituent A C8 cycloalkyl group, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 haloalkenyl group, C2 to C6 alkynyl group optionally substituted with substituent A, C2 to C6 C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group optionally substituted with substituent A, substitution A C2 to C6 alkenyloxy group which may be optionally substituted by a group A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be optionally substituted by a substituent A, C3 C6 haloalkynyloxy group, or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl Or a C3-C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which they are attached form aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl or azocanyl Represents the

Among them, R 1 is a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a C2 to C6 alkenyl group optionally substituted with a substituent A, C2 to C6 halo Alkenyl group, C2-C6 alkynyl group which may be optionally substituted with substituent A, or C2-C6 haloalkynyl group is preferable,
In particular, R 1 is preferably a C 1 to C 6 alkyl group which may be optionally substituted by a substituent A, or a C 1 to C 6 haloalkyl group.

R 1 in the formula (1) includes a hydroxyl group and a cyano group.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with substituent A" in R1 of Formula (1) has the same definition as that described above, preferably a methyl group or an ethyl group A propyl group, an isopropyl group, a butyl group or an isobutyl group, and more preferably a methyl group or an ethyl group. When having a substituent A, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

The “C1-C6 haloalkyl group” in R 1 of the formula (1) is as defined above, preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group or a 2,2,2-trifluoro group. Ethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably 2-fluoroethyl group, 2,2-difluoroethyl group, or 2,2,2- It is a trifluoroethyl group.

The C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent A" in R1 of Formula (1) has the same definition as that described above, and preferably a cyclopropyl group A cyclobutyl group, a cyclopentyl group or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group. When having a substituent A, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent A.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with substituent A" in R1 of Formula (1) has the same definition as that described above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group. When having a substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent A.

The “C2 to C6 haloalkenyl group” in R 1 of the formula (1) is as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or It is a 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

The C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with substituent A” in R 1 of Formula (1) has the same definition as described above, preferably a propargyl group, 2- It is a butynyl group or a 3-butynyl group, and more preferably a propargyl group. When having a substituent A, the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent A.

The “C2-C6 haloalkynyl group” in R 1 of the formula (1) is as defined above, preferably a 4, 4-difluoro-2-butynyl group, 4-chloro-4, 4-difluoro- 2-butynyl group, 4-bromo-4,4-difluoro-2-butynyl group, or 4,4,4-trifluoro-2-butynyl group, more preferably 4,4-difluoro-2-butynyl group Or 4,4,4-trifluoro-2-butynyl group.

The C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with substituent A” in R 1 of Formula (1) has the same definition as that described above, preferably a methoxy group or an ethoxy group A propyloxy group, an isopropyloxy group, a butoxy group or an isobutoxy group, more preferably a methoxy group or an ethoxy group. When having a substituent A, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent A.

The “C1 to C6 haloalkoxy group” in R 1 of the formula (1) is as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group A group or a 2,2,2-trifluoroethoxy group.

The C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group which may be optionally substituted with substituent A" in R1 of the formula (1) has the same definition as that described above, preferably, cyclopropyloxy A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When having a substituent A, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent A.

The C2-C6 alkenyloxy group of the "C2-C6 alkenyloxy group optionally substituted with substituent A" in R1 of Formula (1) has the same definition as that described above, and preferably a vinyloxy group, It is a 1-propenyloxy group or an allyloxy group, and more preferably a vinyloxy group. When having a substituent A, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent A.

The “C2 to C6 haloalkenyloxy group” in R 1 of the formula (1) has the same definition as that described above, and preferably a 2-fluorovinyloxy group, a 2, 2-difluorovinyloxy group, a 3-fluoro It is an allyloxy group or a 3,3-difluoroallyloxy group, and more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

The C3 to C6 alkynyloxy group of the “C3 to C6 alkynyloxy group optionally substituted with substituent A” in R 1 of Formula (1) has the same definition as described above, and preferably a propargyloxy group A 2-butynyloxy group or a 3-butynyloxy group, more preferably a propargyloxy group. When having a substituent A, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.

The “C3-C6 haloalkynyloxy group” in R 1 of the formula (1) has the same meaning as the above-mentioned definition, preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4, 4- It is a difluoro-2-butynyloxy group, a 4-bromo-4,4-difluoro-2-butynyloxy group, or a 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2 Butynyloxy or a 4,4,4-trifluoro-2-butynyloxy group.

“RaRbN—” in R 1 of Formula (1) (where Ra and Rb are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 Represents a haloalkyl group, or a C3 to C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which it is attached is an aziridinyl group, azetidinyl group, pyrrolidinyl group, piperidinyl group, homopiperidinyl group, or azocanyl group The definitions of each of the terms) to be formed are as defined above. In the case of “a C1-C6 alkyl group optionally substituted with a substituent B”, when having a substituent B, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by a substituent B . As "RaRbN-", preferably, amino group, methylamino group, ethylamino group, (methoxymethyl) amino group, (2-methoxyethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, Dimethylamino, ethylmethylamino, diethylamino, (methoxymethyl) methylamino, (2-methoxyethyl) methylamino, (cyanomethyl) methylamino, (2-cyanoethyl) methylamino, 2, 2- Difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group, and piperidinyl group can be mentioned, and more preferably amino group, dimethylamino group , Ethylmethylamino and diethylamino groups It is.

R 2 in the formula (1) is suitably substituted by a hydrogen atom, a nitro group, a halogen atom, a C 1 to C 6 alkyl group optionally substituted by a substituent A, a C 1 to C 6 haloalkyl group, a substituent A C3 to C8 cycloalkyl group, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 haloalkenyl group, C2 to C6 alkynyl optionally substituted with substituent A Group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group optionally substituted with a substituent A, a C1-C6 haloalkoxy group, a C3-C8 cyclo optionally substituted with a substituent A Alkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent A, C2-C6 haloalkenyloxy group, C3-C6 alkynyl optionally substituted with substituent A An oxy group, a C3-C6 haloalkynyl oxy group, Rc-L- (wherein Rc represents a C1-C6 alkyl group, or a C1-C6 haloalkyl group, and L represents S, SO, or SO2; Or RdC (= O) — (wherein, R d is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group Represents the

Among them, R2 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent A, a C1-C6 haloalkyl group, a C1-C6 alkoxy group optionally substituted with substituent A , C1-C6 haloalkoxy group, Rc-L- (wherein Rc and L are as defined above), or RdC (= O)-(wherein Rd is as defined above). Is preferred,
In particular, R2 is preferably a hydrogen atom, a halogen atom, a C1 to C6 alkyl group which may be optionally substituted with substituent A, or a C1 to C6 alkoxy group which may be optionally substituted with substituent A.

R2 in the formula (1) includes a hydrogen atom and a nitro group.

The halogen atom in R 2 of the formula (1) is as defined above, preferably a fluorine, chlorine atom, bromine atom or iodine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with substituent A" in R2 of the formula (1) has the same meaning as defined above, preferably a methyl group or an ethyl group A propyl group, an isopropyl group, a butyl group or an isobutyl group, and more preferably a methyl group or an ethyl group. When having a substituent A, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

The “C1 to C6 haloalkyl group” in R 2 of the formula (1) is as defined above, preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or 2,2,2 -Trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.

The C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent A" in R2 of the formula (1) has the same definition as described above, and preferably a cyclopropyl group A cyclobutyl group, a cyclopentyl group or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group. When having a substituent A, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent A.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with substituent A" in R2 of the formula (1) has the same meaning as defined above, preferably a vinyl group, 1- Propenyl group, allyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. When having a substituent A, a hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent A.

The “C2 to C6 haloalkenyl group” in R 2 of the formula (1) is as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group or a 2,2-dichlorovinyl group And 3-fluoroallyl, 3,3-difluoroallyl or 3,3-dichloroallyl, more preferably 2-fluorovinyl or 2,2-difluorovinyl.

The C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with substituent A” in R 2 of the formula (1) has the same definition as described above, preferably an ethynyl group, 1- Propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group is preferable, and ethynyl group, 1-propynyl group or propargyl group is more preferable. When having a substituent A, the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent A.

The “C2-C6 haloalkynyl group” in R 2 of the formula (1) is as defined above, preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- 2-butynyl group, more preferably 3,3-difluoro-1-propynyl group or 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with substituent A" in R2 of Formula (1) has the same definition as that described above, preferably a methoxy group or an ethoxy group A propyloxy group, an isopropyloxy group, a butoxy group or an isobutoxy group, and more preferably a methoxy group, an ethoxy group, a propyloxy group or an isopropyloxy group. When having a substituent A, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent A.

The “C1 to C6 haloalkoxy group” in R 2 of the formula (1) is as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group A group or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group of the "C3-C8 cycloalkoxy group which may be optionally substituted with substituent A" in R2 of the formula (1) has the same definition as described above, preferably, cyclopropyloxy A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When having a substituent A, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent A.

The C2-C6 alkenyloxy group of the "C2-C6 alkenyloxy group optionally substituted with substituent A" in R2 of Formula (1) has the same definition as that described above, and preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group, or allyloxy group. When having a substituent A, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent A.

The “C2 to C6 haloalkenyloxy group” in R 2 of the formula (1) is as defined above, and is a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2-dichlorovinyloxy group Group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group, or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group or 2,2-difluorovinyloxy group It is.

The C3 to C6 alkynyloxy group of the “C3 to C6 alkynyloxy group optionally substituted with substituent A” in R 2 of Formula (1) has the same definition as that described above, and preferably a propargyloxy group A 2-butynyloxy group or a 3-butynyloxy group, more preferably a propargyloxy group. When having a substituent A, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.

The “C3-C6 haloalkynyloxy group” in R 2 of the formula (1) is as defined above, preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- It is a butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

“Rc-L-” (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO, or SO 2) in R 2 of Formula (1) Each term is as defined above. Preferred as "Rc-L-" is a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.

“RdC (= O) —” in R 2 of Formula (1) (wherein R d is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or C3-C8 And each term of the cycloalkyl group represented by is as defined above. In the case of “a C1-C6 alkyl group optionally substituted with a substituent B”, when having a substituent B, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by a substituent B . As "RdC (= O)-", preferred is an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, or a cyclopropane carbonyl group, and more preferably an acetyl group. Methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group.

X of Formula (1) represents an oxygen atom or a sulfur atom. Preferred X is an oxygen atom.
Y in the formula (1) is an aryl group which may be optionally substituted 0 to 7 with R 3 (provided that R 3 is 2 or more, each of which is independent of each other) or 0 to 4 as appropriate substituted with R 3 And each represents a heteroaryl group (in the case of R3 having 2 or more substituents, each of which is independent of one another). Among them, Y is a phenyl group which may be optionally substituted 0 to 5 with R 3 (provided that they are each independently in the case of R 3 having 2 or more substituents) and a pyridyl group which may be optionally substituted 0 to 4 with R 3 ( However, in the case of R 3 of 2 or more substitution, they are each independently), pyridazinyl group optionally substituted by 0 to 3 with R 3, pyrimidinyl group, or pyrazinyl group (in the case of R 3 of 2 or more substitution, respectively) And triazinyl groups which may be optionally substituted 0 to 2 with R 3 (provided that they are each independently in the case of R 3 being disubstituted) or tetrazinyl group which may be optionally substituted with R 3 Preferably
Furthermore, Y is a phenyl group which may be optionally substituted 0 to 5 with R 3 (provided that they are each independently in the case of R 3 having 2 or more substituents), or a pyridyl group which may be optionally substituted 0 to 4 with R 3 (However, in the case of R3 with 2 or more substituents, they are each independently.) Is preferable,
In particular, Y is preferably a phenyl group which may be optionally substituted 0 to 5 with R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently).

The “phenyl group which may be optionally substituted by 0 to 5 with R 3” in Y of the formula (1) (wherein each R 3 having two or more substituents is independent of each other) is represented by the formula (a) It represents the partial structure shown below.

In formula (a), ma represents an integer of 0 to 5, and when ma is 2 or more, R 3 s of 2 or more substitutions represent independent substituents, which may be the same or different and may be selected arbitrarily it can.

The “pyridyl group which may be optionally substituted by 0 to 4 with R 3” in Y of the formula (1) (wherein each R 3 having two or more substituents is independent of each other) has a formula (b-1), a formula The partial structure shown below with (b-2) and Formula (b-3) is represented.

In formulas (b-1), (b-2) and (b-3), mb represents an integer of 0 to 4, and in the case where mb is 2 or more, two or more substituted R3's are independent substituents. And may be the same or different and can be arbitrarily selected.

The “pyridazinyl group which may be optionally substituted 0 to 3 with R 3” in Y of the formula (1) (provided that R 3 s each having 2 or more substituents are independent of each other) has a formula (c-1), a formula The partial structure shown below with (c-2) and Formula (c-3) is represented.

In formulas (c-1), (c-2) and (c-3), mc represents an integer of 0 to 3, and when mc is 2 or more, two or more substituted R3's are independent substituents. And may be the same or different and can be arbitrarily selected.

The “pyrimidinyl group which may be optionally substituted 0 to 3 with R 3” in Y of the formula (1) (but each of R 3 s having 2 or more substituents is independent of each other) has a formula (d-1), a formula The partial structure shown below with (d-2) and Formula (d-3) is represented.

In formulas (d-1), (d-2) and (d-3), md represents an integer of 0 to 3, and when md is 2 or more, two or more substituted R3's are independent substituents. And may be the same or different and can be arbitrarily selected.

The “pyrazinyl group optionally substituted by 0 to 3 with R 3 (wherein each R 3 is 2 or more substituents, each independently)” in Y of Formula (1) is represented by Formula (e) It represents the partial structure shown below.

In formula (e), me represents an integer of 0 to 3, and when me is 2 or more, two or more substituted R 3 s independently represent an independent substituent, which may be the same or different and may be selected arbitrarily it can.

The “triazinyl group optionally substituted with 0 to 2 R 3 as appropriate” in Y of the formula (1) (but in the case of disubstituted R 3, each of which is independent of each other) has a formula (f-1) or a formula The partial structure shown below represented by f-2), Formula (f-3), Formula (f-4), and Formula (f-5) is represented.

In formulas (f-1), (f-2), (f-3), (f-4) and (f-5), mf represents an integer of 0 to 2, and mf is 2 In the case, each disubstituted R 3 represents an independent substituent, which may be the same or different, and can be optionally selected.

The “tetradinyl group which may be optionally substituted with R 3” in Y of the formula (1) is a moiety represented by the following formulas (g-1), (g-2) and (g-3) Represents a structure.

In formulas (g-1), (g-2) and (g-3), mg represents an integer of 0 to 1.

R3 in the formula (1) is optionally substituted with a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a substituent C C3-C8 cycloalkyl group which may be substituted, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent C C 2 -C 6 haloalkynyl group, C 1 -C 6 alkoxy group optionally substituted with substituent C, C 1-C 6 haloalkoxy group, C 3 -C 8 optionally substituted with substituent C Of C2 to C6 alkenyloxy group optionally substituted with substituent C, C2 to C6 haloalkenyloxy group, C3 to C6 optionally substituted with substituent C A luminyloxy group, a C3-C6 haloalkynyl oxy group, RaRbN- (wherein Ra and Rb are as defined above), Rc-L- (where Rc and L are as defined above). ) Rx1C (= O)-(wherein, Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1-C6 Or an alkoxy group of C1 to C6, a haloalkoxy group of C1 to C6, a cycloalkoxy group of C3 to C8, or RaRbN- (wherein, Ra and Rb are as defined above), or Rx1C (OO) O. -(Here, Rx1 is the same as the above).

Among them, R 3 is a hydroxyl group, a cyano group, a halogen atom, a C 1 to C 6 alkyl group optionally substituted with substituent C, a C 1 to C 6 haloalkyl group, C 1 to C 6 optionally substituted with substituent C Alkoxy group, C1-C6 haloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 optionally substituted with substituent C A C6 alkynyloxy group, a C3 to C6 haloalkynyloxy group, or Rx1C (= O) O— (wherein Rx1 is as defined above) is preferable,
Particularly, R3 is a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent C, a C1 to C6 alkoxy group optionally substituted with substituent C, a substituent C C2-C6 alkenyloxy group which may be optionally substituted, C3-C6 alkynyloxy group which may be optionally substituted with substituent C, or Rx1C (= O) O- (wherein Rx1 is as defined above) Is preferred.

R 3 in the formula (1) includes a hydroxyl group, a cyano group and a nitro group.

The halogen atom in R 3 of the formula (1) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with substituent C" in R3 of the formula (1) has the same meaning as defined above, preferably a methyl group or an ethyl group A propyl group, an isopropyl group, a butyl group or an isobutyl group, and more preferably a methyl group, an ethyl group, a propyl group or an isopropyl group. When having a substituent C, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent C.

The “C1 to C6 haloalkyl group” in R 3 of the formula (1) is as defined above, preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, 2,2,2 -Trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.

The C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent C" in R3 of Formula (1) has the same definition as that described above, and preferably a cyclopropyl group A cyclobutyl group, a cyclopentyl group or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group. When having a substituent C, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent C.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group which may be optionally substituted with substituent C" in R3 of Formula (1) has the same meaning as defined above, preferably a vinyl group, 1- Propenyl group, allyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. When having a substituent C, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.

The “C2 to C6 haloalkenyl group” in R 3 of the formula (1) is as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group or a 2,2-dichlorovinyl group And 3-fluoroallyl, 3,3-difluoroallyl or 3,3-dichloroallyl, more preferably 2-fluorovinyl or 2,2-difluorovinyl.

The C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with substituent C” in R 3 of the formula (1) has the same definition as described above, preferably an ethynyl group, 1— Propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group is preferable, and ethynyl group, 1-propynyl group or propargyl group is more preferable. When having a substituent C, the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent C.

The “C2-C6 haloalkynyl group” in R 3 of the formula (1) is as defined above, preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- 2-butynyl group, more preferably 3,3-difluoro-1-propynyl group or 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with substituent C" in R3 of Formula (1) has the same definition as that described above, preferably a methoxy group or an ethoxy group A propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group or a pentyloxy group, and more preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group or a butoxy group. When having a substituent C, a hydrogen atom in the C1 to C6 alkoxy group is optionally substituted by the substituent C.

The “C1 to C6 haloalkoxy group” in R 3 of the formula (1) is as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group A group or a 2,2,2-trifluoroethoxy group.

The C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group optionally substituted with substituent C" in R3 of the formula (1) has the same definition as that described above, preferably, cyclopropyloxy A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When having a substituent C, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent C.

The C2-C6 alkenyloxy group of the "C2-C6 alkenyloxy group which may be optionally substituted with substituent C" in R3 of Formula (1) has the same definition as described above, and preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group, or allyloxy group. When having a substituent C, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent C.

The “C2 to C6 haloalkenyloxy group” in R 3 of the formula (1) is as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, or 2,2- Dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group, or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group, or 2,2-difluoro It is a vinyloxy group.

The C3-C6 alkynyloxy group of the "C3-C6 alkynyloxy group optionally substituted with substituent C" in R3 of the formula (1) has the same definition as that described above, and preferably a propargyloxy group A 2-butynyloxy group or a 3-butynyloxy group, more preferably a propargyloxy group. When having a substituent C, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent C.

The “C3-C6 haloalkynyloxy group” in R 3 of the formula (1) is as defined above, preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- It is a butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

Ra and Rb of "RaRbN-" in R3 of Formula (1) are as defined above. As "RaRbN-", preferably, amino, methylamino, ethylamino, propylamino, isopropylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) amino, (2-cyanoethyl) amino group, dimethylamino group, ethyl (methyl) amino group, methyl (propyl) amino group, isopropyl (methyl) amino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group (Cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, diethylamino group, ethyl (propyl) amino group, ethyl (isopropyl) amino group, ethyl (methoxymethyl) amino group, ethyl (2-methoxyethyl) amino Group, (cyanomethyl) ethylamino group, (2- Annoethyl) ethylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group, or piperidinyl group, and Preferably, it is a dimethylamino group, an ethyl (methyl) amino group, an isopropyl (methyl) amino group, a diethylamino group, or an ethyl (isopropyl) amino group.

Rc and L of "Rc-L-" in R3 of Formula (1) are as defined above. Preferred as "Rc-L-" is a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.

“Rx1C (= O) —” in R3 of Formula (1) (wherein Rx1 is a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 A cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (wherein, Ra and Rb are as defined above). The definition of each term is as defined above. In the case of “a C1-C6 alkyl group optionally substituted with a substituent B”, when having a substituent B, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by a substituent B . As “Rx 1 C (= O) —”, preferably, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, 2 , 2-Difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoethyl) aminocarbonyl group, dimethylaminocarbonyl group, ethyl (meth ) Aminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl) methylaminocarbonyl group, (2-methoxyethyl) methylaminocarbonyl group, (cyanomethyl) methylaminocarbonyl group, (2-cyanoethyl) methylaminocarbonyl group, 2,2 -Difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, cyclopropyl (methyl) aminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, More preferably, they are acetyl, methoxyacetyl, cyanoacetyl, difluoroacetyl, trifluoroacetyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, dimethylaminocarboyl. Group, ethyl (methyl) aminocarbonyl groups or diethylamino group.

Rx1 of “Rx1C (= O) O—” in R3 of Formula (1) has the same meaning as described above. As "Rx1C (= O) O-", preferably, acetyloxy, methoxyacetyloxy, cyanoacetyloxy, propionyloxy, difluoroacetyloxy, trifluoroacetyloxy, cyclopropanecarbonyloxy, methoxy Carbonyloxy, ethoxycarbonyloxy, 2,2-difluoroethoxycarbonyloxy, 2,2,2-trifluoroethoxycarbonyloxy, 3,3,3-trifluoropropyloxycarbonyloxy, cyclopropyloxycarbonyl Oxy group, amino carbonyloxy group, methylamino carbonyloxy group, ethyl amino carbonyloxy group, (methoxymethyl) amino carbonyloxy group, (2-methoxyethyl) amino carbonyloxy group, (sia (Methyl) aminocarbonyloxy group, (2-cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethyl (methyl) aminocarbonyloxy group, diethylamino carbonyloxy group, (methoxymethyl) methylamino carbonyloxy group, (2- (Methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl) methylaminocarbonyloxy group, (2-cyanoethyl) methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylamino A carbonyloxy group, a cyclopropylamino carbonyloxy group, a cyclopropyl (methyl) amino carbonyloxy group, a pyrrolidinyl carbonyloxy group, or a piperidinyl carbonyloxy group; More preferably, acetyloxy, methoxyacetyloxy, cyanoacetyloxy, difluoroacetyloxy, trifluoroacetyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, aminocarbonyloxy, dimethylaminocarbonyloxy, It is an ethyl (methyl) amino carbonyloxy group or a diethyl amino carbonyloxy group.

Z in the formula (1) is an aryl group which may be optionally substituted 0 to 7 with R 4 (wherein each R 4 having 2 or more substituents is independent of each other) or 0 to 6 as appropriate substituted with R 4 And optionally represents a heterocyclic group which may be independent of each other in the case of R 4 having 2 or more substituents.

Among them, Z is a phenyl group which may be optionally substituted 0 to 5 with R 4 (wherein each R 4 is independently substituted in the case of R 4), and a naphthyl group which may be optionally substituted 0 to 7 with R 4 ( However, in the case of R 4 having 2 or more substituents, they are each independently pyridyl), pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl or tetrazinyl which may be optionally substituted 0 to 4 with R 4 (wherein, In the case of R 4 of two or more substituents, they are each independently), thienyl group which may be optionally substituted 0 to 3 with R 4, thiazolyl group, isothiazolyl group, thiadiazolyl group, or thiatriazolyl group (with the proviso that R4 is disubstituted or more) Pyrrolyl group, pyrazolyl group, imidazolyl group, triazo group which may be optionally substituted by 0 to 4 as appropriate. Group, tetrazolyl group, or pentazolyl group (provided that they are each independently in the case of R4 having 2 or more substituents), furyl group optionally substituted by 0 to 3 with R4, oxazolyl group, isoxazolyl group, oxadiazolyl group Or an oxatriazolyl group (provided that each R4 is independently substituted in the case of 2 or more R4), an indolyl group optionally substituted by 0 to 6 with R4, an isoindolyl group, an indazolyl group, a benzoimidazolyl group, or A benzotriazolyl group (provided that they are each independently in the case of R4 having 2 or more substituents), and a benzofuryl group, an isobenzofuryl group, a benzoxazolyl group, a benzo group which may be optionally substituted by 0 to 5 with R4 Isoxazolyl group, or benzoxadiazolyl group (in the case of R 4 having 2 or more substituents, respectively) And R 4 each optionally be substituted by 0 to 5 benzothienyl group, benzothiazolyl group, benzoisothiazolyl group, or benzothiadiazolyl group (in the case of R 4 having two or more substituents, each of which is independent of each other) And R 4 optionally have 0 to 6 substitution with an indolizinyl group, an imidazo pyridyl group, a pyrazolo pyridyl group, or a triazolo pyridyl group (in the case of R 4 having two or more substituents, each of which is independent of each other) And pyrrolopyrimidinyl group optionally substituted by 0 to 5 with R 4, imidazopyrimidinyl group, pyrazolopyrimidinyl group, or triazolopyrimidinyl group (in the case of two or more substituted R 4, they are each independently.) , Pyrrolopyrazinyl group optionally substituted 0 to 5 with R 4, imidazopyrazinyl group, pyrazolopyrazinyl group A group or a triazolopyrazinyl group (provided that R4 is disubstituted or more, each of which is independent of each other). And quinolinyl group optionally substituted with 0 to 6 by R 4, isoquinolyl group, cinolyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, or naphthyridinyl group (in the case of R 4 having two or more substituents, each of which is independent of each other) Or a 3 to 6 membered ring group containing 1 or 2 oxygen atoms,
Further, Z is a phenyl group which may be optionally substituted 0 to 5 with R 4 (provided that they are each independently in the case of R 4 having 2 or more substituents), and a pyridyl group which may be optionally substituted 0 to 4 with R 4, A pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group (provided that they are each independently in the case of R4 having 2 or more substituents), a thienyl group optionally having 0 to 3 substitution with R4, a thiazolyl group , Isothiazolyl group, thiadiazolyl group, or thiatriazolyl group (provided that they are each independently in the case of R4 having 2 or more substituents), pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group which may be optionally substituted by 0 to 4 as appropriate. Group, a tetrazolyl group, or a pentazolyl group (with the proviso that in the case of R4 having 2 or more substituents, each is independent And furyl group optionally substituted by 0 to 3 with R 4, oxazolyl group, isoxazolyl group, oxadiazolyl group, or oxatriazolyl group (provided that they are each independently in the case of R 4 having two or more substituents). Preferably
Particularly, Z is a phenyl group which may be optionally substituted 0 to 5 with R 4 (provided that each is independently in the case of R 4 having 2 or more substituents), a pyrazolyl group which may be optionally substituted 0 to 4 with R 4, An imidazolyl group, a triazolyl group (provided that they are each independently in the case of R4 having 2 or more substituents), an oxazolyl group optionally substituted by 0 to 3 with R4, or an isoxazolyl group (note that R4 having 2 or more substituents) In each case, they are preferably independent of each other).

The “phenyl group which may be optionally substituted by 0 to 5 with R 4” in Z of Formula (1) (wherein each R 4 having two or more substituents is independent of each other) is represented by Formula (h) It represents the partial structure shown below.

Na in the formula (h) represents an integer of 0 to 5.

When na in the formula (h) is 2 or more, two or more substituents R4 each independently represent a substituent, which may be the same or different and can be arbitrarily selected.

The “a naphthyl group which may be optionally substituted with 0 to 7 R 4 in Z of Formula (1)” (wherein each R 4 having two or more substituents is independent of each other) is represented by Formula (i) It represents the partial structure shown below.

In the formula (i), nb represents an integer of 0 to 7.

When nb in the formula (i) is 2 or more, R4s each having 2 or more substituents represent independent substituents, which may be the same or different, and can be arbitrarily selected.

“In the case of R 4 having two or more substituents, each of pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl or tetrazinyl” in Z of Formula (1) (wherein each of R 4 may be optionally substituted 0 to 4 optionally with 0 to 4 substitution) (Independent) represents the partial structure shown below with formula (j).

G1, G2, G3, G4 and G5 in Formula (j) are each independently a carbon atom or a nitrogen atom. However, at least one of G1, G2, G3, G4, and G5 is a nitrogen atom. In preferred G1, G2, G3, G4 and G5, any one of G1, G2, G3, G4 and G5 is a nitrogen atom. That is, it is a pyridyl group.

In the formula (j), nc represents an integer of 0 to 4.

When nc in the formula (j) is 2 or more, two or more substituents R4 each independently represent a substituent, which may be the same or different, and can be arbitrarily selected.

The specific example of the partial structure of Formula (j) is shown below.

In Z of Formula (1), “a thienyl group which may be optionally substituted by R 4, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, or a thiatriazolyl group” (in the case of two or more substituted R 4, each independently Are the following partial structures represented by the formula (k-1) and the formula (k-2).

G6, G7 and G8 in Formula (k-1) and Formula (k-2) are each independently represent a carbon atom or a nitrogen atom.

In the formulas (k-1) and (k-2), nd represents an integer of 0 to 3.

When nd in the formula (k-1) and the formula (k-2) is 2 or more, two or more substituted R4's each independently represent a substituent, which may be the same or different and may be optionally selected it can.

Specific examples of the partial structure of formula (k-1) are shown below.

Specific examples of the partial structure of formula (k-2) are shown below

“In the case of R 4 having two or more substituents, each of“ a pyrrolyl group optionally substituted with 0 to 4 R 4 optionally having 0 to 4 substitution with R 4, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group or a pentazolyl group ”in Z of Formula (1) Independently)) represents a partial structure shown below which is represented by formula (1-1), formula (1-2), and formula (1-3).

G9, G10, G11 and G12 in Formula (1-1), Formula (1-2) and Formula (1-3) are each independently a carbon atom or a nitrogen atom.

In the formulas (I-1), (I-2) and (I-3), ne represents an integer of 0 to 4.

When ne in the formula (I-1), the formula (I-2) and the formula (I-3) is 2 or more, two or more substituted R 4 s independently represent an independent substituent and may be the same or different. , Can be selected arbitrarily.

Specific examples of the partial structure of formula (I-1) are shown below.

Specific examples of the partial structure of formula (I-2) are shown below.

Specific examples of the partial structure of Formula (l-3) are shown below.

“In the case of R 4 having two or more substituents, each of“ a furyl group optionally substituted with 0 to 4 R 4 optionally having 0 to 3 substitution with R 4, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group or an oxatriazolyl group ”in Z of Formula (1) (Independent) represents a partial structure shown by the formula (m-1) and the formula (m-2) shown below.

G13, G14 and G15 in Formula (m-1) and Formula (m-2) are each independently represent a carbon atom or a nitrogen atom.

Nf in the formulas (m-1) and (m-2) represents an integer of 0 to 3.

When nf in the formula (m-1) and the formula (m-2) is 2 or more, two or more substituted R4's each independently represent a substituent, which may be the same or different and may be optionally selected it can.

Specific examples of the partial structure of Formula (m-1) are shown below.

Specific examples of the partial structure of Formula (m-2) are shown below.

“Indolyl group optionally substituted with 0 to 6 optionally with R 4, isoindolyl group, indazolyl group, benzoimidazolyl group or benzotriazolyl group” in Z of Formula (1) (however, in the case of R 4 having two or more substituents, each of them Independently)) represents a partial structure shown by Formula (n-1) and Formula (n-2) below.

G16 and G17 in Formula (n-1) and Formula (n-2) are each independently represent a carbon atom or a nitrogen atom.

In the formulas (n-1) and (n-2), ng represents an integer of 0 to 6.

When ng in the formula (n-1) and the formula (n-2) is 2 or more, two or more substituted R4's each independently represent a substituent, which may be the same or different and may be optionally selected it can.

Specific examples of the partial structure of the formula (n-1) are shown below.

Specific examples of the partial structure of Formula (n-2) are shown below.

“A benzofuryl group which may be optionally substituted by 0 to 4, an isobenzofuryl group, a benzoxazolyl group, a benzoisoxazolyl group or a benzooxadiazolyl group” in Z of the formula (1) (wherein, In the case of R 4 having 2 or more substituents, they are each independently.) Represents a partial structure shown below as represented by Formula (о-1) and Formula (о-2).

G18 and G19 in Formula (о-1) and Formula (о-2) are each independently represent a carbon atom or a nitrogen atom.

Nh in the formulas (о-1) and (о-2) represents an integer of 0 to 5.

When nh in the formula (о-1) and the formula (о-2) is 2 or more, two or more substituted R 4 s independently represent an independent substituent, which may be the same or different and may be optionally selected it can.

Specific examples of the partial structure of Formula (о-1) are shown below.

Specific examples of the partial structure of Formula (о-2) are shown below.

“In the case of R 4 having two or more substituents,“ a benzothienyl group which may be optionally substituted with 0 to 4 R 4, a benzothiazolyl group, a benzoisothiazolyl group, or a benzothiadiazolyl group ”in Z of Formula (1) And each independently represents a partial structure shown by the formula (p-1) and the formula (p-2) shown below.

G20 and G21 in Formula (p-1) and Formula (p-2) are each independently a carbon atom or a nitrogen atom.

In the formulas (p-1) and (p-2), ni represents an integer of 0 to 5.

When ni in the formula (p-1) and the formula (p-2) is 2 or more, two or more substituted R4's each independently represent a substituent, which may be the same or different and may be optionally selected it can.

Specific examples of the partial structure of Formula (p-1) are shown below.

Specific examples of the partial structure of Formula (p-2) are shown below.

“Indolizinyl group optionally substituted with 0 to 6 R 4 optionally substituted with R 4, imidazo pyridyl group, pyrazolo pyridyl group, or triazolo pyridyl group” in Z of Formula (1) (however, in the case of R 4 having two or more substituents, each independently ) Represents a partial structure shown by the following formula (q).

G22, G23 and G24 in Formula (q) are each independently a carbon atom or a nitrogen atom.

N j in the formula (q) represents an integer of 0 to 6.

When n j in the formula (q) is 2 or more, two or more substituents R 4 each represent an independent substituent, which may be the same or different, and can be selected arbitrarily.

The specific example of the partial structure of Formula (q) is shown below.

The pyrrolopyrimidinyl group optionally substituted with 0 to 5 substituents for R 4 in formula (1), imidazo pyrimidinyl group, pyrazolo pyrimidinyl group, triazolo pyrimidinyl group, pyrrolo pyrazinyl group, imidazo pyrazinyl group, pyrazolo pyrazinyl Group or a triazolopyrazinyl group (in the case of R4 having 2 or more substituents, each of which is independent of each other) is a group represented by the formula (r-1), the formula (r-2), and the formula (r-3) It represents the partial structure shown below).

G25, G26 and G27 in formulas (r-1), (r-2) and formula (r-3) are each independently a carbon atom or a nitrogen atom.

In the formulas (r-1), (r-2) and the formula (r-3), nk represents an integer of 0 to 5.

When nk in the formulas (r-1), (r-2) and the formula (r-3) is 2 or more, two or more substituted R4's each independently represent a substituent, which may be the same or different, It can be selected arbitrarily.

Specific examples of the partial structure of Formula (r-1) are shown below.

Specific examples of the partial structure of Formula (r-2) are shown below.

Specific examples of the partial structure of Formula (r-3) are shown below.

“In the case of R 4 having two or more substituents, each of“ a quinolyl group optionally substituted with 0 to 4 R 4 may be optionally substituted with R 4, isoquinolyl group, cinolyl group, phthalazinyl group, quinoxalinyl group or quinazolinyl group ”in Z of Formula (1) (Independent) represents a partial structure shown by the formula (s-1) and the formula (s-2) shown below.

G28, G29, G30, and G31 in Formula (s-1) and Formula (s-2) are each independently a carbon atom or a nitrogen atom. However, at least one of G28, G29, G30, and G31 is a nitrogen atom. In formula (s-1), as preferred G26, G27, G28 and G29, one of G26, G27, G28 and G29 is a nitrogen atom. That is, it is a quinolyl group.

In the formulas (s-1) and (s-2), nl represents an integer of 0 to 6.

When n1 in the formula (s-1) and the formula (s-2) is 2 or more, two or more R.sup.4 each represents an independent substituent, which may be the same or different and may be selected arbitrarily it can.

Specific examples of the partial structure of Formula (s-1) are shown below.

Specific examples of the partial structure of Formula (s-2) are shown below.

The “3 to 6-membered ring group containing one or two oxygen atoms” in the formula (1) is as defined above, preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, Or a 1,3-dioxanyl group, more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

R 4 in the formula (1) is optionally substituted with a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a substituent C C3-C8 cycloalkyl group which may be substituted, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent C C 2 -C 6 haloalkynyl group, C 1 -C 6 alkoxy group optionally substituted with substituent C, C 1-C 6 haloalkoxy group, C 3 -C 8 optionally substituted with substituent C Of C2 to C6 alkenyloxy group optionally substituted with substituent C, C2 to C6 haloalkenyloxy group, C3 to C6 optionally substituted with substituent C The lucinyloxy group, the C3-C6 haloalkynyl oxy group, the aryl group which may be suitably substituted with the substituent D, the heteroaryl group which may be suitably substituted with the substituent D, the aryl which may be suitably substituted with the substituent D Oxy group, heteroaryloxy group which may be optionally substituted with substituent D, aralkyloxy group which may be optionally substituted with substituent D, RaRbN- (wherein, Ra and Rb are as defined above) , Rc-L- (wherein Rc and L are as defined above), Rx1C (= O)-(wherein Rx1 is as defined above), Rx1C (= O) O- (Here, Rx1 is the same as the above.), Or Rx2C (NO) N (Rx3)-(where Rx2 is a hydrogen atom, C1 to C6 optionally substituted with a substituent B. Alkyl group, C1 to 6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above) And Rx 3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group. Represents

Among them, R 4 is a hydroxyl group, a halogen atom, a C 1 to C 6 alkyl group optionally substituted with a substituent C, a C 1 to C 6 haloalkyl group, a C 2 to C 6 alkenyl group optionally substituted with a substituent C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyl optionally substituted with substituent C Oxy group, C3-C6 haloalkynyl oxy group, Rc-L- (wherein Rc and L are as defined above), Rx1C (= O)-(wherein Rx1 is The same meanings as defined above.), Or Rx1C (= O) O- (wherein, Rx1 has the same meaning as defined above.) Is preferred,
In particular, R 4 is preferably a halogen atom, a C 1 to C 6 alkyl group which may be optionally substituted with a substituent C, or a C 1 to C 6 alkoxy group which may be optionally substituted with a substituent C.

R 4 in the formula (1) includes a hydroxyl group, a cyano group and a nitro group.

The halogen atom in R 4 of the formula (1) is as defined above, and is preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The C1-C6 alkyl group of the “C1-C6 alkyl group optionally substituted with substituent C” in R 4 of Formula (1) has the same definition as described above, and preferably a methyl group or an ethyl group A propyl group, an isopropyl group, a butyl group or an isobutyl group, and more preferably a methyl group, an ethyl group, a propyl group or an isopropyl group. When having a substituent C, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent C.

The “C1 to C6 haloalkyl group” in R 4 of the formula (1) is as defined above, preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, 2,2,2 -Trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.

The C3 to C8 cycloalkyl group of the "C3 to C8 cycloalkyl group optionally substituted with substituent C" in R4 of the formula (1) has the same meaning as described above, preferably a cyclopropyl group A cyclobutyl group, a cyclopentyl group or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group. When having a substituent C, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent C.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group optionally substituted with substituent C" in R4 of the formula (1) has the same definition as described above, and preferably a vinyl group, 1- Propenyl group, allyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. When having a substituent C, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.

The “C2 to C6 haloalkenyl group” in R 4 of the formula (1) is as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group or a 2,2-dichlorovinyl group And 3-fluoroallyl, 3,3-difluoroallyl or 3,3-dichloroallyl, more preferably 2-fluorovinyl or 2,2-difluorovinyl.

The C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with substituent C” in R 4 of the formula (1) has the same definition as described above, preferably an ethynyl group, 1- Propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group is preferable, and ethynyl group, 1-propynyl group or propargyl group is more preferable. When having a substituent C, the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent C.

The “C2-C6 haloalkynyl group” in R 4 of the formula (1) is as defined above, preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- 2-butynyl group, more preferably 3,3-difluoro-1-propynyl group or 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the "C1-C6 alkoxy group optionally substituted with substituent C" in R4 of the formula (1) has the same definition as described above, preferably a methoxy group or an ethoxy group A propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group or a pentyloxy group, and more preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group or a butoxy group. When having a substituent C, a hydrogen atom in the C1 to C6 alkoxy group is optionally substituted by the substituent C.

The “C1 to C6 haloalkoxy group” in R 4 of the formula (1) is as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group A group or a 2,2,2-trifluoroethoxy group.

The C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group which may be optionally substituted with substituent C" in R4 of the formula (1) has the same definition as that described above, preferably, cyclopropyloxy A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When having a substituent C, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent C.

The C2-C6 alkenyloxy group of the "C2-C6 alkenyloxy group optionally substituted with substituent C" in R4 of the formula (1) has the same definition as described above, preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group, or allyloxy group. When having a substituent C, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent C.

The “C2 to C6 haloalkenyloxy group” in R 4 of the formula (1) is as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, or 2,2- Dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group, or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group, or 2,2-difluoro It is a vinyloxy group.

The C3 to C6 alkynyloxy group of the “C3 to C6 alkynyloxy group optionally substituted with substituent C” in R 4 of Formula (1) has the same definition as that described above, and preferably a propargyloxy group A 2-butynyloxy group or a 3-butynyloxy group, more preferably a propargyloxy group. When having a substituent C, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent C.

The “C3-C6 haloalkynyloxy group” in R 4 of the formula (1) is as defined above, preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- It is a butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

The aryl group of the “aryl group which may be optionally substituted with the substituent D” in R 4 of the formula (1) has the same definition as the above. Preferably, it is a phenyl group or a naphthyl group, more preferably a phenyl group. When having a substituent D, the hydrogen atom in the aryl group is optionally substituted by the substituent D.

The heteroaryl group of the “heteroaryl group which may be optionally substituted with the substituent D” in R 4 of the formula (1) has the same definition as the above. Preferably, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, thiatriazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group. , Pentazolyl group, furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group or oxatriazolyl group, more preferably pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thienyl group, thiazolyl group, isothiazolyl group, Thiadiazolyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, furyl group, oxazolyl group, isoxazolyl group, or oxadiazolyl group. When having a substituent D, the hydrogen atom in the heteroaryl group is optionally substituted by the substituent D.

The aryloxy group of "an aryloxy group which may be optionally substituted with a substituent D" in R 4 of the formula (1) has the same definition as the above. Preferably, it is a phenoxy group or a naphthyloxy group, more preferably a phenoxy group. When having a substituent D, the hydrogen atom in the aryloxy group is optionally substituted by the substituent D.

The heteroaryloxy group of “the heteroaryloxy group which may be optionally substituted with the substituent D” in R 4 of the formula (1) is as defined above. Preferably, pyridyloxy group, pyridazinyloxy group, pyrimidinyloxy group, pyrazinyloxy group, triazinyloxy group, tetradinyloxy group, thienyloxy group, thiazolyloxy group, isothiazolyloxy group, thiadiazolyloxy group Group, thiatriazolyloxy group, pyrrolyloxy group, pyrazolyloxy group, imidazolyloxy group, triazolyloxy group, tetrazolyloxy group, pentazolyloxy group, furyloxy group, oxazolyloxy group, isoxazolyl And more preferably a pyridyloxy group, a pyridazinyloxy group, a pyrimidinyloxy group, a pyrazinyloxy group, a thienyloxy group, a thiazolyloxy group, or an isothioxy group. Azolyloxy group, Asian benzotriazolyl group, pyrrolyloxy group, a pyrazolyloxy group, imidazolyloxy group, triazolyl group, furyl group, benzoxazolyl group, benzisoxazolyl group or oxadiazolyl group. When having a substituent D, the hydrogen atom in the heteroaryloxy group is optionally substituted by the substituent D.

The aralkyloxy group of the “aralkyloxy group which may be optionally substituted with the substituent D” in R 4 of the formula (1) has the same definition as the above. Preferably, it is a benzyloxy group, a phenethyloxy group, or a naphthylmethyloxy group, and more preferably a benzyloxy group or a phenethyloxy group. When having a substituent D, the hydrogen atom in the aralkyloxy group is optionally substituted by the substituent D.

Ra and Rb of "RaRbN-" in R4 of Formula (1) are as defined above. As "RaRbN-", preferably, amino, methylamino, ethylamino, propylamino, isopropylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) amino, (2-cyanoethyl) amino group, dimethylamino group, ethyl (methyl) amino group, methyl (propyl) amino group, isopropyl (methyl) amino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group (Cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, diethylamino group, ethyl (propyl) amino group, ethyl (isopropyl) amino group, ethyl (methoxymethyl) amino group, ethyl (2-methoxyethyl) amino Group, (cyanomethyl) ethylamino group, (2- Annoethyl) ethylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group, or piperidinyl group, and Preferably, it is a dimethylamino group, an ethyl (methyl) amino group, an isopropyl (methyl) amino group, a diethylamino group, or an ethyl (isopropyl) amino group.

Rc and L of "Rc-L-" in R4 of Formula (1) are as defined above. Preferred as "Rc-L-" is a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.

Rx1 of "Rx1C (= O)-" in R4 of Formula (1) is as defined above. As “Rx 1 C (= O) —”, preferably, acetyl group, methoxyacetyl group, cyanoacetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, 2 , 2-Difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, methylaminocarbonyl group, ethylamino Carbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoethyl) aminocarbonyl group, dimethylaminocarbonyl group, ethyl (meth ) Aminocarbonyl group, diethylaminocarbonyl group, (methoxymethyl) methylaminocarbonyl group, (2-methoxyethyl) methylaminocarbonyl group, (cyanomethyl) methylaminocarbonyl group, (2-cyanoethyl) methylaminocarbonyl group, 2,2 -Difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, cyclopropyl (methyl) aminocarbonyl group, pyrrolidinylcarbonyl group, or piperidinylcarbonyl group, More preferably, they are acetyl, methoxyacetyl, cyanoacetyl, difluoroacetyl, trifluoroacetyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, dimethylaminocarboyl. Group, ethyl (methyl) aminocarbonyl groups or diethylamino group.

Rx1 of “Rx1C (= O) O—” in R4 of Formula (1) has the same meaning as described above. As "Rx1C (= O) O-", preferably, acetyloxy, methoxyacetyloxy, cyanoacetyloxy, propionyloxy, difluoroacetyloxy, trifluoroacetyloxy, cyclopropanecarbonyloxy, methoxy Carbonyloxy, ethoxycarbonyloxy, 2,2-difluoroethoxycarbonyloxy, 2,2,2-trifluoroethoxycarbonyloxy, 3,3,3-trifluoropropyloxycarbonyloxy, cyclopropyloxycarbonyl Oxy group, amino carbonyloxy group, methylamino carbonyloxy group, ethyl amino carbonyloxy group, (methoxymethyl) amino carbonyloxy group, (2-methoxyethyl) amino carbonyloxy group, (sia (Methyl) aminocarbonyloxy group, (2-cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethyl (methyl) aminocarbonyloxy group, diethylamino carbonyloxy group, (methoxymethyl) methylamino carbonyloxy group, (2- (Methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl) methylaminocarbonyloxy group, (2-cyanoethyl) methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylamino A carbonyloxy group, a cyclopropylamino carbonyloxy group, a cyclopropyl (methyl) amino carbonyloxy group, a pyrrolidinyl carbonyloxy group, or a piperidinyl carbonyloxy group; More preferably, acetyloxy, methoxyacetyloxy, cyanoacetyloxy, difluoroacetyloxy, trifluoroacetyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, aminocarbonyloxy, dimethylaminocarbonyloxy, It is an ethyl (methyl) amino carbonyloxy group or a diethyl amino carbonyloxy group.

“Rx2C (= O) N (Rx3) —” in R4 of the formula (1) (wherein Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, C1-C6 A haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above) Rx3 represents a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group. The definition of terms is as defined above. In the case of “a C1-C6 alkyl group optionally substituted with a substituent B”, when having a substituent B, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by a substituent B . As Rx2, preferably, a hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, ethoxy group, 2, 2-difluoroethoxy, 2,2-trifluoroethoxy, cyclopropyloxy, amino, methylamino, ethylamino, (methoxymethyl) amino, (2-methoxyethyl) amino, (cyanomethyl) amino, (2- Cyanoethyl) amino group, dimethylamino group, ethylmethylamino group, diethylamino group, (methoxymethyl) methylamino group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group , 2,2-difluoroethylamino group, 2,2,2-to Fluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl group or piperidinyl group, more preferably a hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, difluoromethyl group, trifluoro It is a methyl group, a methoxy group, an ethoxy group, an amino group, a dimethylamino group, an ethylmethylamino group or a diethylamino group. As Rx 3, preferably, a hydrogen atom, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-cyanoethyl group, a propyl group, 2-difluoroethyl group, 2,2,2-trifluoroethyl group, or cyclopropyl group, more preferably hydrogen atom, methyl group, methoxymethyl group, cyanomethyl group, ethyl group, 2-methoxyethyl group, It is a 2,2-difluoroethyl group or a 2,2,2-trifluoroethyl group.

W in the formula (1) represents a C1 to C6 alkylene group which may be optionally substituted 0 to 2 with R 5.

Among them, W is preferably a methylene group which may be optionally substituted 0 to 2 with R 5, or an ethylene group,
In particular, W is preferably a methylene group which may be optionally substituted 0 to 2 with R 5.

The alkylene group of “a C1 to C6 alkylene group optionally substituted by 0 to 2 R 5 optionally for W in the formula (1)” has the same meaning as defined above, preferably a methylene group or an ethylene group And more preferably a methylene group. When having a substituent R5, the hydrogen atom in the C1-C6 alkylene group is optionally substituted by the substituent R5.

R5 in the formula (1) may be optionally substituted with a hydroxyl group, a cyano group, a halogen atom, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a substituent C A good C3 to C8 cycloalkyl group, a C2 to C6 alkenyl group optionally substituted with a substituent C, a C2 to C6 haloalkenyl group, a C2 to C6 alkynyl group optionally substituted with a substituent C , A C2 to C6 haloalkynyl group, a C1 to C6 alkoxy group optionally substituted with a substituent C, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy optionally substituted with a substituent C Group, C2-C6 alkenyloxy group which may be optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyl which may be optionally substituted with substituent C Xy group, a C3-C6 haloalkynyl oxy group, Rc-L- (wherein Rc and L are as defined above), or Rx1C (= O)-(wherein Rx1 is as defined above) Represents the

Among them, R5 is a hydroxyl group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent C, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group optionally substituted with a substituent C, C1-C6 haloalkoxy group, C2-C6 alkenyloxy group optionally substituted with substituent C, C2-C6 haloalkenyloxy group, C3-C6 alkynyl optionally substituted with substituent C An oxy group, a C3-C6 haloalkynyloxy group, or Rx1C (= O)-(wherein Rx1 is as defined above) is preferable,
In particular, R5 is preferably a hydroxyl group, a halogen atom, or a C1 to C6 alkoxy group which may be optionally substituted by a substituent C.

R 5 in the formula (1) includes a hydroxyl group and a cyano group.

The halogen atom in R5 of the formula (1) is as defined above, preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The C1-C6 alkyl group of the "C1-C6 alkyl group optionally substituted with substituent C" in R5 of Formula (1) has the same definition as described above, and preferably a methyl group or an ethyl group A propyl group, an isopropyl group, a butyl group or an isobutyl group, and more preferably a methyl group, an ethyl group, a propyl group or an isopropyl group. When having a substituent C, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent C.

The “C1 to C6 haloalkyl group” in R 5 of the formula (1) is as defined above, preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, 2,2,2 -Trifluoroethyl group, 3,3-difluoropropyl group, or 3,3,3-trifluoropropyl group, more preferably difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.

The C3 to C8 cycloalkyl group of the “C3 to C8 cycloalkyl group optionally substituted with substituent C” in R 5 of Formula (1) has the same definition as described above, and preferably a cyclopropyl group A cyclobutyl group, a cyclopentyl group or a cyclohexyl group, more preferably a cyclopropyl group or a cyclobutyl group. When having a substituent C, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent C.

The C2-C6 alkenyl group of the "C2-C6 alkenyl group which may be optionally substituted with substituent C" in R5 of the formula (1) has the same meaning as defined above, preferably a vinyl group, 1- Propenyl group, allyl group, 1-butenyl group, 2-butenyl group, or 3-butenyl group, more preferably vinyl group, 1-propenyl group or allyl group. When having a substituent C, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.

The “C2 to C6 haloalkenyl group” in R 5 of the formula (1) is as defined above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group or a 2,2-dichlorovinyl group And 3-fluoroallyl, 3,3-difluoroallyl or 3,3-dichloroallyl, more preferably 2-fluorovinyl or 2,2-difluorovinyl.

The C2 to C6 alkynyl group of the “C2 to C6 alkynyl group optionally substituted with substituent C” in R 5 of the formula (1) has the same definition as described above, preferably an ethynyl group, 1- Propynyl group, propargyl group, 1-butynyl group, 2-butynyl group or 3-butynyl group is preferable, and ethynyl group, 1-propynyl group or propargyl group is more preferable. When having a substituent C, the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent C.

The “C2-C6 haloalkynyl group” in R 5 of the formula (1) is as defined above, preferably a 3,3-difluoro-1-propynyl group, 3,3,3-trifluoro-1 -Propynyl group, 4,4-difluoro-1-butynyl group, 4,4-difluoro-2-butynyl group, 4,4,4-trifluoro-1-butynyl group, or 4,4,4-trifluoro- 2-butynyl group, more preferably 3,3-difluoro-1-propynyl group or 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with substituent C” in R 5 of Formula (1) has the same definition as that described above, preferably a methoxy group or an ethoxy group A propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group or a pentyloxy group, and more preferably a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group or a butoxy group. When having a substituent C, a hydrogen atom in the C1 to C6 alkoxy group is optionally substituted by the substituent C.

The “C1 to C6 haloalkoxy group” in R 5 of the formula (1) is as defined above, preferably a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, 2,2, 2-trifluoroethoxy group, 3,3-difluoropropyloxy group, or 3,3,3-trifluoropropyloxy group, more preferably difluoromethoxy group, trifluoromethoxy group, 2,2-difluoroethoxy group A group or a 2,2,2-trifluoroethoxy group.

The C3 to C8 cycloalkoxy group of the "C3 to C8 cycloalkoxy group which may be optionally substituted with substituent C" in R 5 of the formula (1) has the same definition as that described above, preferably, cyclopropyloxy A cyclobutoxy group, a cyclopentyloxy group or a cyclohexyloxy group, more preferably a cyclopropyloxy group or a cyclobutoxy group. When having a substituent C, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent C.

The C2-C6 alkenyloxy group of the "C2-C6 alkenyloxy group optionally substituted with substituent C" in R5 of Formula (1) has the same definition as described above, and preferably a vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, or 3-butenyloxy group, more preferably vinyloxy group, 1-propenyloxy group, or allyloxy group. When having a substituent C, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent C.

The “C2 to C6 haloalkenyloxy group” in R 5 of the formula (1) is as defined above, preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, or 2,2- Dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoroallyloxy group, or 3,3-dichloroallyloxy group, more preferably 2-fluorovinyloxy group, or 2,2-difluoro It is a vinyloxy group.

The C3 to C6 alkynyloxy group of the “C3 to C6 alkynyloxy group optionally substituted with substituent C” in R 5 of the formula (1) has the same definition as that described above, preferably a propargyloxy group A 2-butynyloxy group or a 3-butynyloxy group, more preferably a propargyloxy group. When having a substituent C, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent C.

The “C3-C6 haloalkynyloxy group” in R 5 of the formula (1) is as defined above, preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4-difluoro -2-butynyloxy group, 4-bromo-4,4-difluoro-2-butynyloxy group, or 4,4,4-trifluoro-2-butynyloxy group, more preferably 4,4-difluoro-2- It is a butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

Rc and L of “Rc-L-” in R 5 of Formula (1) are as defined above. Preferred as "Rc-L-" is a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, or a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group Or a methanesulfonyl group.

Rx1 of “Rx1C (= O) O—” in R5 of Formula (1) has the same meaning as described above. As "Rx1C (= O) O-", preferably, acetyloxy, methoxyacetyloxy, cyanoacetyloxy, propionyloxy, difluoroacetyloxy, trifluoroacetyloxy, cyclopropanecarbonyloxy, methoxy Carbonyloxy, ethoxycarbonyloxy, 2,2-difluoroethoxycarbonyloxy, 2,2,2-trifluoroethoxycarbonyloxy, 3,3,3-trifluoropropyloxycarbonyloxy, cyclopropyloxycarbonyl Oxy group, amino carbonyloxy group, methylamino carbonyloxy group, ethyl amino carbonyloxy group, (methoxymethyl) amino carbonyloxy group, (2-methoxyethyl) amino carbonyloxy group, (sia (Methyl) aminocarbonyloxy group, (2-cyanoethyl) aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethyl (methyl) aminocarbonyloxy group, diethylamino carbonyloxy group, (methoxymethyl) methylamino carbonyloxy group, (2- (Methoxyethyl) methylaminocarbonyloxy group, (cyanomethyl) methylaminocarbonyloxy group, (2-cyanoethyl) methylaminocarbonyloxy group, 2,2-difluoroethylaminocarbonyloxy group, 2,2,2-trifluoroethylamino A carbonyloxy group, a cyclopropylamino carbonyloxy group, a cyclopropyl (methyl) amino carbonyloxy group, a pyrrolidinyl carbonyloxy group, or a piperidinyl carbonyloxy group; More preferably, acetyloxy, methoxyacetyloxy, cyanoacetyloxy, difluoroacetyloxy, trifluoroacetyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, aminocarbonyloxy, dimethylaminocarbonyloxy, It is an ethyl (methyl) amino carbonyloxy group or a diethyl amino carbonyloxy group.

Substituent group A is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, RaRbN- (wherein Ra and Rb And Rc are as defined above), and Rc-L- (wherein Rc and L are as defined above), and at least one selected from the group consisting of

Among them, the substituent A is preferably a cyano group, a C1-C6 alkoxy group or Rc-L- (wherein Rc and L are as defined above).
In particular, a cyano group or a C1-C6 alkoxy group is preferable.

Each term of the substituent A is as defined above.

With respect to the preferred specific examples of the substituent A, hydroxyl group; cyano group;
A cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group as a C3-C8 cycloalkyl group;
As a C1 to C6 alkoxy group, a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
As a C1-C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and 3,3 as a C1-C6 haloalkoxy group. , 3-trifluoropropyloxy group;
A cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group as a C3-C8 cycloalkoxy group;
As RaRbN- (wherein Ra and Rb are as defined above), amino, methylamino, ethylamino, propylamino, isopropylamino, (methoxymethyl) amino, (2-methoxy) Ethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethyl (methyl) amino group, methyl (propyl) amino group, isopropyl (methyl) amino group, (methoxymethyl) methyl amino Group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, diethylamino group, ethyl (propyl) amino group, ethyl (isopropyl) amino group, ethyl (methoxymethyl) group Amino group, ethyl (2-methoxyethyl) amino group, Methyl) ethylamino group, (2-cyanoethyl) ethylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl And piperidinyl groups;
And Rc-L- (wherein Rc and L are as defined above) includes a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group It can be mentioned.

With respect to further preferred specific examples of the substituent A, a hydroxyl group; a cyano group;
A cyclopropyl group and a cyclobutyl group as a C3-C8 cycloalkyl group;
A methoxy group and an ethoxy group as a C1 to C6 alkoxy group;
As a C1-C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
A cyclopropyloxy group and a cyclobutoxy group as a C3 to C8 cycloalkoxy group;
A dimethylamino group, an ethyl (methyl) amino group, and a diethylamino group as RaRbN- (wherein Ra and Rb are as defined above);
And Rc-L- (wherein Rc and L are as defined above) include a methylthio group, a methanesulfinyl group, and a methanesulfonyl group.

The substituent B represents at least one selected from the group consisting of a cyano group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, and a C3 to C8 cycloalkoxy group.

Among them, the substituent B is preferably a cyano group or a C1-C6 alkoxy group.

Each term of substituent B is as defined above.

With respect to preferred examples of substituent B, a cyano group;
As a C1 to C6 alkoxy group, a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
As a C1-C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and 3,3 as a C1-C6 haloalkoxy group. , 3-trifluoropropyloxy group;
And a C3-C8 cycloalkoxy group includes cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group, and cyclohexyloxy group.

With respect to further preferred embodiments of the substituent B, a cyano group;
A methoxy group and an ethoxy group as a C1 to C6 alkoxy group;
As a C1-C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
And C3-C8 cycloalkoxy groups include cyclopropyloxy and cyclobutoxy.

The substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN -(Wherein, Ra and Rb are as defined above), Rc-L- (wherein, Rc and L are as defined above), Rx1C (= O)-(wherein, Rx1 And at least one member selected from the group consisting of groups having 3 to 6 members each containing 1 to 2 oxygen atoms.

Among them, the substituent C is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, Rc-L- (wherein Rc and L are as defined above, or Rx1C ((O) — (wherein, Rx1 is as defined above) is preferable,
In particular, a hydroxyl group or a C1 to C6 alkoxy group is preferable.

Each term of substituent C is as defined above.

With respect to the preferred specific examples of the substituent C, a hydroxyl group; a cyano group;
A cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group as a C3-C8 cycloalkyl group;
As a C1 to C6 alkoxy group, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
As a C1-C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and 3,3 as a C1-C6 haloalkoxy group. , 3-trifluoropropyloxy group;
A cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group as a C3-C8 cycloalkoxy group;
As a C2 to C6 alkoxyalkoxy group, a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, an ethoxyethoxy group, and a methoxypropyloxy group;
As a C2 to C6 alkoxyalkoxy group, a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, an ethoxyethoxy group, and a methoxypropyloxy group;
As RaRbN- (wherein Ra and Rb are as defined above), amino, methylamino, ethylamino, propylamino, isopropylamino, (methoxymethyl) amino, (2-methoxy) Ethyl) amino group, (cyanomethyl) amino group, (2-cyanoethyl) amino group, dimethylamino group, ethyl (methyl) amino group, methyl (propyl) amino group, isopropyl (methyl) amino group, (methoxymethyl) methyl amino Group, (2-methoxyethyl) methylamino group, (cyanomethyl) methylamino group, (2-cyanoethyl) methylamino group, diethylamino group, ethyl (propyl) amino group, ethyl (isopropyl) amino group, ethyl (methoxymethyl) group Amino group, ethyl (2-methoxyethyl) amino group, Methyl) ethylamino group, (2-cyanoethyl) ethylamino group, 2,2-difluoroethylamino group, 2,2,2-trifluoroethylamino group, cyclopropylamino group, (cyclopropyl) methylamino group, pyrrolidinyl And piperidinyl groups;
Rc-L- (wherein Rc and L are as defined above) includes methylthio, methanesulfinyl, methanesulfonyl, trifluoromethylthio, trifluoromethanesulfinyl, and trifluoromethanesulfonyl;
As Rx1C (= O) — (wherein Rx1 has the same meaning as the above), an acetyl group, a methoxyacetyl group, a cyanoacetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropane carbonyl group, Methoxycarbonyl group, ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl Group, methylaminocarbonyl group, ethylaminocarbonyl group, (methoxymethyl) aminocarbonyl group, (2-methoxyethyl) aminocarbonyl group, (cyanomethyl) aminocarbonyl group, (2-cyanoethyl) aminocarbonyl group, dimethylaminoca Bonyl, ethyl (methyl) aminocarbonyl, diethylaminocarbonyl, (methoxymethyl) methylaminocarbonyl, (2-methoxyethyl) methylaminocarbonyl, (cyanomethyl) methylaminocarbonyl, (2-cyanoethyl) methylamino A carbonyl group, 2,2-difluoroethylaminocarbonyl group, 2,2,2-trifluoroethylaminocarbonyl group, cyclopropylaminocarbonyl group, (cyclopropyl) methylaminocarbonyl group, pyrrolidinyl carbonyl group, and piperidine A nyl carbonyl group;
And 3- to 6-membered ring groups containing 1 to 2 oxygen atoms include oxolanyl group, oxanyl group, 1,3-dioxolanyl group, and 1,3-dioxanyl group.

With respect to further preferred specific examples of the substituent C, a hydroxyl group; a cyano group;
A cyclopropyl group and a cyclobutyl group as a C3-C8 cycloalkyl group;
A methoxy group and an ethoxy group as a C1 to C6 alkoxy group;
As a C1-C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
A cyclopropyloxy group, a cyclobutoxy group as a C3-C8 cycloalkoxy group;
As a C2 to C6 alkoxyalkoxy group, a methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, and an ethoxyethoxy group;
A dimethylamino group, an ethyl (methyl) amino group, and a diethylamino group as RaRbN- (wherein Ra and Rb are as defined above);
Methylthio group, methanesulfinyl group, and methanesulfonyl group as Rc-L- (wherein Rc and L are as defined above);
As Rx1C (= O) — (wherein, Rx1 has the same meaning as the above.), An acetyl group, a methoxyacetyl group, a cyanoacetyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxycarbonyl group, Aminocarbonyl group, dimethylaminocarbonyl group, ethyl (methyl) aminocarbonyl group, and diethylaminocarbonyl group;
And, as a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, 1,3-dioxolanyl and 1,3-dioxanyl may be mentioned.

Substituent D includes a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, C1 to C6. It represents at least one selected from the group consisting of a C6 alkoxy group, a C1 to C6 haloalkoxy group, and a C3 to C8 cycloalkoxy group.

Among them, the substituent D is a hydroxyl group, a cyano group, a halogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, and a C1 to C6 halo. An alkoxy group is preferred,
In particular, a halogen atom, a C1-C6 alkyl group which may be optionally substituted with a substituent B, and a C1-C6 alkoxy group are preferable.

Each term of substituent D is as defined above. In the case of “a C1-C6 alkyl group optionally substituted with a substituent B”, when having a substituent B, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by a substituent B .

With regard to the preferred specific examples of the substituent D, hydroxyl group; cyano group; nitro group;
As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom;
As a C1 to C6 alkyl group which may be optionally substituted by substituent B, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, 2-cyanoethyl group , Propyl, isopropyl, butyl and isobutyl;
As a C 1 to C 6 haloalkyl group, difluoromethyl group, trifluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 3,3-difluoropropyl group, and 3,3,3 -Trifluoropropyl group;
A cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group as a C3-C8 cycloalkyl group;
As a C1 to C6 alkoxy group, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
As a C1-C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and 3,3 as a C1-C6 haloalkoxy group. , 3-trifluoropropyloxy group;
And a C3-C8 cycloalkoxy group includes cyclopropyloxy group, cyclobutoxy group, cyclopentyloxy group, and cyclohexyloxy group.

With respect to further preferred specific examples of the substituent D, a hydroxyl group; a cyano group; a nitro group;
As a halogen atom, a fluorine atom, a chlorine atom and a bromine atom;
As a C1 to C6 alkyl group which may be optionally substituted by substituent B, a methyl group, a methoxymethyl group, an ethoxymethyl group, a cyanomethyl group, an ethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, and 2- Cyanoethyl group;
As a C1 to C6 haloalkyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group;
A cyclopropyl group and a cyclobutyl group as a C3-C8 cycloalkyl group;
As a C1 to C6 alkoxy group, a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group;
As a C1-C6 haloalkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group;
And C3 to C8 cycloalkoxy groups include cyclopropyloxy and cyclobutoxy.

The compound represented by Formula (1) may have axial asymmetry. The isomer ratio in this case is a single or arbitrary mixing ratio, and is not particularly limited.

The compound represented by formula (1) may contain an asymmetric atom. The isomer ratio in this case is a single or arbitrary mixing ratio, and is not particularly limited.

The compounds represented by formula (1) may contain geometric isomers. The isomer ratio in this case is a single or arbitrary mixing ratio, and is not particularly limited.

The compound represented by Formula (1) may be able to form a salt. Examples include acid salts such as hydrochloric acid, sulfuric acid, acetic acid, fumaric acid and maleic acid, metal salts such as sodium, potassium and calcium, etc., but they are particularly limited as long as they can be used as agricultural and horticultural fungicides There is no.

Next, specific compounds of the present invention are structural formulas shown in Table 1 (P-1 to P-28: provided that X in the structural formula is oxygen or sulfur), Y shown in Table 2 It is represented by a combination of Y-1 to Y-86), W (W-1 to W-48) shown in Table 3 and Z (Z-001 to Z-1710) shown in Table 4.

These compounds are for illustration and the present invention is not limited thereto.

In Table 3, the partial structure represented by Wa is represented by the formula (Wa) shown below.

In Table 3, the partial structure represented by Wb is represented by the formula (Wb) shown below.

The partial structure represented by Wb in Table 3 is represented by the formula (Wc) shown below

Hereinafter, a method for producing the compound represented by the formula (1) of the present invention is shown. The method for producing the compound of the present invention is not limited to production methods A to Q.

[Manufacturing method A]

In the formula, U 1 represents a C 1 to C 6 alkyl group, a C 1 to C 6 aralkyl group, or a C 1 to C 6 heteroaralkyl group, R 8 represents a hydrogen atom or a C 1 to C 6 alkyl group, R 2, X and Y represent , And the same as the above.

Production method A is a method for producing a compound represented by the formula (4) which is a production intermediate of the compound of the present invention, and when it is represented by the formula (2), a compound represented by the formula (3) And a reaction in the presence of a base in a solvent.

The compound represented by Formula (2) used for this reaction can be obtained as a commercial item, or can be manufactured using a reference example or a well-known method.

The compound represented by Formula (3) used for this reaction can be obtained as a commercial item, or can be manufactured by a well-known method.

The amount of the compound represented by the formula (3) used in the present reaction is particularly limited as long as the target reaction proceeds, provided that the amount is 1 equivalent or more with respect to the compound represented by the formula (2) Although it is not, it is usually 1 equivalent or more and 3 equivalents or less.

Bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and tripotassium phosphate, and metal alkoxides such as sodium methoxide, sodium ethoxide, sodium t-butoxide and potassium t-butoxide Etc.

The base used for this reaction is not particularly limited as long as the target reaction proceeds, but is usually 0.01 equivalent or more and 3 equivalents or less with respect to the compound represented by Formula (2) .

Solvents used for this reaction include ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc. Ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl Urea solvents such as -2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, sulfur solvents such as dimethylsulfoxide and sulfolane, acetone, methyl ethyl ketone, methyl Ketone solvents such as Sobuchiruketon like. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by Formula (2). is there.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually −50 ° C. or more and 150 ° C. or less or the boiling point or less of the solvent.

For post-treatment of the reaction, it is possible to carry out a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and may be carried out depending on the desired purity and yield. The reaction mixture containing the compound represented by the formula (4) obtained above is sodium sulfate and Although water can be removed by a desiccant such as magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (4) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (4) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method B]

In the formula, R 8 a represents a C 1 to C 6 alkyl group, and R 2, X, Y and U 1 are as defined above.

Production method B is a method for obtaining a production intermediate represented by formula (4b) among the compounds represented by formula (4), wherein the compound represented by formula (4a) is subjected to acidic conditions or base conditions It is a manufacturing method including reacting in a solvent under sexual conditions.

First, the reaction under acidic conditions will be described.

Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid and phosphoric acid, and organic acids such as acetic acid, methanesulfonic acid, p-toluenesulfonic acid and trifluoroacetic acid. There is no particular limitation as long as the target reaction proceeds.

The amount of the acid used in this reaction may be a catalytic amount, and is not particularly limited as long as the target reaction proceeds, but generally 0.01 relative to the compound represented by formula (4a) It is more than equivalent. Moreover, it is also possible to use as a solvent regarding liquid acid.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is not limited to an aqueous solvent, an acidic solvent such as acetic acid or methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t- Ether solvents such as butyl ether, dimethoxyethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ethyl acetate, isopropyl acetate, acetic acid Ester solvents such as butyl, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone and the like C A solvent, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by Formula (4a). is there.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually 0 ° C. or more and 180 ° C. or less or the boiling point or less of the solvent.

Next, the reaction under basic conditions will be described.

Examples of the base used in this reaction include inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide, but there is no particular limitation as long as the target reaction proceeds.

The base used in this reaction is not particularly limited as long as the target reaction proceeds, provided that it has 1 equivalent or more relative to the compound represented by Formula (4a), but usually 1 equivalent or more. It is less than equivalent weight.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but water solvents, diethyl ether, diisopropyl ether, methyl-t-butyl ether, ethers such as dimethoxyethane, tetrahydrofuran, dioxane, etc. Solvents, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitriles such as acetonitrile Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloromethane Down, chloroform, and halogen solvents such as carbon tetrachloride. These solvents may be used alone or in combination of two or more in any proportion.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually −20 ° C. or more and 180 ° C. or less or the boiling point or less of the solvent.

Post-treatment of the reaction can be carried out in a common manner between the reaction under acidic conditions and the reaction under basic conditions. A liquid separation operation can be performed by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield.

Although the reaction mixture containing the compound represented by Formula (4b) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (4b) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (4b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

The compound represented by the formula (4b) is a compound represented by the formula (4b ′)

(Wherein R 2, X, Y and U 1 are as defined above)
It also includes the isomer represented by

The compound represented by the formula (4b ′) can be handled in the same manner as the compound represented by the formula (4b), and can be applied to, for example, the production method C. In addition, although the compound represented by the formula (4b ') contains an asymmetric carbon, the isomer mixing ratio may be a single one or a mixture of any ratio. Furthermore, it may be a mixture of the compound represented by the formula (4b) and the compound represented by the formula (4b ′), and the isomer mixing ratio may be a single or a mixture of any ratio.

[Manufacturing method C]

In the formula, R 9 represents a hydrogen atom, a hydroxyl group, a cyano group, a C 1 to C 6 alkyl group optionally substituted with substituent A, a C 1 to C 6 haloalkyl group, C 3 optionally substituted with substituent A C8 cycloalkyl group, C2 to C6 alkenyl group optionally substituted with substituent A, C2 to C6 haloalkenyl group, C2 to C6 alkynyl group optionally substituted with substituent A, C2 to C6 C6 haloalkynyl group, C1 to C6 alkoxy group optionally substituted with substituent A, C1 to C6 haloalkoxy group, C3 to C8 cycloalkoxy group optionally substituted with substituent A, substitution A C2 to C6 alkenyloxy group which may be optionally substituted by a group A, a C2 to C6 haloalkenyloxy group, a C3 to C6 alkynyloxy group which may be optionally substituted by a substituent A, 3 ~ haloalkynyloxy group C6, or RaRbN- (wherein, Ra and Rb have the same meanings as defined above.) Represent, R2, R8, X, Y and U1 are as defined above.

Manufacturing method C, the present invention is a production intermediate of the compound A method of obtaining a compound represented by the formula (5), a compound R1NH ₂ of the formula (4), the reaction in the presence of an acid Manufacturing method including the step of

R9NH ₂ used in this reaction can be produced by obtaining or known manner as a commercially available product. R9NH ₂ are hydrochloric, may be those forming a salt with an acidic compound such as acetic acid, it is not particularly limited as long as the reaction proceeds to the desired.

R9NH ₂ used in this reaction may be at least 1 equivalent with respect to the compound represented by Formula (4), and is not particularly limited as long as the target reaction proceeds, but usually 1 equivalent More than 200 equivalents.

Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, methanesulfonic acid and p-toluenesulfonic acid, and there is no particular limitation as long as the target reaction proceeds. None but is preferably acetic acid. Further, when using salts of R9NH ₂ and the acidic compound, the use of acid is not essential.

The amount of the acid used in this reaction may be 1 equivalent or more with respect to R 9 NH ₂ , and is not particularly limited as long as the target reaction proceeds, but is usually 1 equivalent or more and 200 equivalents or less . When the acid used is a liquid, it can also be used as a solvent.

Although a solvent can be used for this reaction, it is not necessarily essential.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as acetic acid and methanesulfonic acid, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxymethane Ether solvents such as ethane, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ethyl acetate, isopropyl acetate and butyl acetate Ester solvents, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, and urea solvents such as 1,3-dimethyl-2-imidazolidinone Melting , Dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents may be used alone or in combination of two or more in any proportion. As a solvent, Preferably, an acidic solvent is mentioned, More preferably, an acetic acid is mentioned.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by Formula (4). is there.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually 50 ° C. or more and 180 ° C. or less or the boiling point or less of the solvent.

For post-treatment of the reaction, it is possible to carry out a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield.

Although the reaction mixture containing the compound represented by Formula (5) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (5) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (5) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method D]

In the formula, Lv represents a leaving group such as methanesulfonyl group, trifluoromethanesulfonyl group, p-toluenesulfonyl group, halogen atom and the like, and R 1, R 2, X, Y and U 1 are as defined above.

Production method D is a method for obtaining a compound represented by the formula (5b), which is a production intermediate of the compound of the present invention, and the compound represented by the formula (5a) and R1-Lv in the presence of a base It is a manufacturing method including reacting in a solvent.

The compound represented by the formula (5a), which is a raw material of the present invention, can be produced by the production method C or Journal of Heterocyclic Chemistry (Journal of OH Chemistry), Vol. 20, pp. 65-67 (1983). Non-patent documents such as J. et al.

R1-Lv used for this reaction can be obtained as a commercial item or can be produced by a known method.

Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride and the like, but are particularly limited as long as the target reaction proceeds. It will not be done.

The amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (5a), and is not particularly limited as long as the target reaction proceeds, but usually 1 It is equal to or more than 10 equivalents.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. Alcohol solvents such as methanol, ethanol and isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, Amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane, Chloroform, halogenated solvents such as carbon tetrachloride, dimethyl sulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by Formula (5a). is there.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually 0 ° C. or more and 150 ° C. or less or the boiling point or less of the solvent.

Although the reaction mixture containing the compound represented by Formula (5b) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (5b) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (5b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method E]

In the formula, SR represents a sulfurizing agent, and R 1, R 2, Y and U 1 are as defined above.

Production method E is a method for obtaining the compound represented by the formula (5b-2) among the compounds represented by the formula (5b), wherein the compound represented by the formula (5b-1) and the sulfurizing agent It is a manufacturing method including making (SR) react in a solvent.

Examples of the sulfurizing agent used in the present reaction include Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide).

The amount of the sulfurizing agent used in this reaction may be 0.5 equivalents or more with respect to the compound represented by the formula (5b-1), and is particularly limited as long as the target reaction proceeds Although it is not, it is usually 1 equivalent or more and 10 equivalents or less.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. Benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene and the like can be mentioned. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 times by weight or more and 200 times by weight the compound represented by the formula (5b-1) It is below.

For post-treatment of the reaction, it is possible to carry out a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield. In addition, liquid separation operation is not essential in this reaction.

Although the reaction mixture containing the compound represented by the formula (5b-2) obtained above can be freed of moisture with a desiccant such as sodium sulfate or magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (5b-2) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (5b-2) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method F]

In the formula, R 2a is a C 1 to C 6 alkyl group which may be optionally substituted with a substituent A, a C 1 to C 6 haloalkyl group, a C 3 to C 8 cycloalkyl group which may be optionally substituted with a substituent A, a substituent C2-C6 alkenyl group optionally substituted with A, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent A, C2-C6 haloalkynyl group, or RdC (= O)-(wherein, Rd is as defined above), and R 1, X, Y, U 1 and Lv are as defined above.

In the compound represented by the formula (5b), the production method F is suitably substituted with a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, and a substituent A of R2a. C3-C8 cycloalkyl group which may be substituted, C2-C6 alkenyl group which may be optionally substituted by substituent A, C2-C6 haloalkenyl group, C2-C6 which may be optionally substituted by substituent A A method of obtaining a compound represented by the formula (5b-4) which is an alkynyl group, a C2 to C6 haloalkynyl group, or RdC (CO) — (wherein Rd is as defined above). And the reaction of reacting the compound represented by the formula (5b-3) with R2a-Lv in a solvent in the presence of a base.

R2a-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.

The amount of R2a-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by Formula (5b-3), and is not particularly limited as long as the target reaction proceeds. Usually, it is 1 equivalent or more and 1.8 equivalents or less.

As a base used for this reaction, metal hydrides such as sodium hydride, organolithiums such as methyllithium, butyllithium, sec-butyllithium, t-butyllithium, hexyllithium, lithium diisopropylamide, hexamethyldisilazane Metal amides such as lithium, hexamethyldisilazane sodium and hexamethyldisilazane potassium are exemplified.

The amount of the base used in this reaction may be 1 equivalent or more to the compound represented by the formula (5b-3), and is not particularly limited as long as the target reaction proceeds, 1 equivalent or more and 10 equivalents or less.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. Examples thereof include benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 times by weight or more and 200 times by weight the compound represented by the formula (5b-3) It is below.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually −80 ° C. or more and 100 ° C. or less or the boiling point or less of the solvent.

For post-treatment of the reaction, it is possible to carry out a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Adding a solvent which is not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane and chloroform, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield.

Although the reaction mixture containing the compound represented by the formula (5b-4) obtained above can be freed of water with a desiccant such as sodium sulfate or magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (5b-4) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (5b-4) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method G]

In the formula, Ox represents an oxidizing agent, and R 1, R 2, X, Y and U 1 are as defined above.

Production method G is a method for obtaining a compound represented by the formula (6) which is a production intermediate of the compound of the present invention, which comprises the compound represented by the formula (5b) and an oxidizing agent (Ox) in a solvent Manufacturing method comprising reacting at.

As an oxidizing agent used in this reaction, metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, azobisisobutyronitrile, benzoyl peroxide and the like Radical initiators of N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3- A combination of a halogenating agent such as diiodo-5,5-dimethylhydantoin can be used.

Hereinafter, a method in which the oxidizing agent is a metal oxide will be described.

The amount of the oxidizing agent used in this reaction is not particularly limited as long as the target reaction proceeds, provided that the amount is 1 equivalent or more with respect to the compound represented by Formula (5b). It is equal to or more than 200 equivalents.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but benzene, toluene, xylene, mesitylene, benzene, such as chlorobenzene, dichlorobenzene, dichloromethane, dichloroethane, chloroform, Halogen solvents such as carbon tetrachloride and the like can be mentioned. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 times by weight or more and 200 times by weight or less with respect to the compound represented by Formula (5b) is there.

As post-treatment of the reaction, it is possible to remove undissolved metals by filtration. Furthermore, it is possible to carry out a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield. In addition, separation operation is not essential in this reaction.

Although the reaction mixture containing the compound represented by Formula (6) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (6) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (6) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like using an appropriate solvent. It may be appropriately set according to the target purity.

Hereinafter, the method in which the oxidizing agent is benzoquinones will be described.
The amount of the oxidizing agent used in this reaction is not particularly limited as long as the target reaction proceeds, provided that the amount is 1 equivalent or more with respect to the compound represented by formula (5b). It is equal to or more than 20 equivalents.

For post-treatment of the reaction, it is possible to carry out a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield. In addition, separation operation is not essential in this reaction.

Hereinafter, a method in which the oxidizing agent is a combination of a radical initiator and a halogenating agent will be described.

If the amount of the radical initiator and the halogenating agent used in this reaction is 0.01 equivalent or more and 1.0 equivalent or more, respectively, to the compound represented by the formula (5b), the target reaction proceeds There is no particular limitation as far as it is. Usually, the radical initiator is 0.01 equivalent or more and 1 equivalent or less, and the halogenating agent is 1 equivalent or more and 3 equivalents or less.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but halogenated benzene solvents such as chlorobenzene and dichlorobenzene, and esters such as ethyl acetate, isopropyl acetate and butyl acetate Examples thereof include solvents, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents may be used alone or in combination of two or more in any proportion.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually 20 ° C. or more and 150 ° C. or less or the boiling point or less of the solvent.

[Manufacturing method H]

In the formula, R 2 b represents a halogen atom, Hal R represents a halogenating agent, and R 1, X, Y and U 1 are as defined above.

Production method H is a method for obtaining a compound represented by the formula (6b) in which R 2 b represents a halogen atom, and the compound represented by the formula (6a) is reacted with a halogenating agent (HalR) in a solvent Manufacturing method including the step of

As a halogenating agent used for this reaction, selectrofluor (N-fluoro-N'-triethylenediamine bis (tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1 2,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin, 1,3-diiodo-5,5-dimethylhydantoin, bromine, iodine and the like.

The amount of the halogenating agent used in this reaction is not particularly limited as long as the target reaction proceeds, provided that the amount is at least 1 equivalent with respect to the compound represented by formula (6a). 1 to 10 equivalents. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the target reaction proceeds as long as the amount of the halogenating agent containing the hydantoin is 0.5 equivalents or more.

When the halogenating agent used in this reaction is an iodizing agent, add an acid such as an inorganic acid such as hydrochloric acid or sulfuric acid, or an organic acid such as acetic acid, trifluoroacetic acid, methanesulfonic acid, or trifluoromethanesulfonic acid Can.

When the amount of the acid used when the halogenating agent used in this reaction is an iodination agent is 0.01 equivalent or more to the compound represented by the formula (6a), the target reaction proceeds Although there is no particular limitation in the limitation, it is usually 0.1 equivalent or more and 3 equivalents or less.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but acidic solvents such as sulfuric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, etc., diethyl ether Ether solvents such as diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. Alcohol solvents such as methanol, ethanol, isopropanol etc. Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene etc Ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, and N, N-dimethylacetamide 1,3-dimethyl-2-urea-based solvent-imidazolidinone, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by formula (6a) is there.

Although the reaction mixture containing the compound represented by Formula (6b) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (6b) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (6b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Production method I]

In the formula, J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, R2c is a C1 to C6 alkyl group optionally substituted with a substituent A, a C1 to C6 haloalkyl group, a substituent A C3-C8 cycloalkyl group which may be optionally substituted, C2-C6 alkenyl group which may be optionally substituted by substituent A, C2-C6 haloalkenyl group, C2 which may be optionally substituted by substituent A R 2 c represents a C 1 to C 6 alkynyl group, a C 2 to C 6 haloalkynyl group, and when J is a sulfur atom, R 2 c represents a C 1 to C 6 alkyl group or a C 1 to C 6 haloalkyl group, and Q represents a hydrogen atom or a metal R1, R2b, X, Y and U1 are as defined above.

In the production method I, J represents an oxygen atom or a sulfur atom, and when J is an oxygen atom, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, a substituent A C3-C8 cycloalkyl group optionally substituted by A, a C2-C6 alkenyl group optionally substituted by a substituent A, a C2-C6 haloalkenyl group, optionally substituted by a substituent A Represents a good C2 to C6 alkynyl group or a C2 to C6 haloalkynyl group, and when J is a sulfur atom, R2c is a group represented by the formula (6c) representing a C1 to C6 alkyl group or a C1 to C6 haloalkyl group A method for obtaining a compound, which comprises obtaining a compound represented by the formula (6b) and R2c-J-Q by a coupling reaction in which they are reacted in the presence of transition metals.

In the compound represented by the formula (6b), preferable R2b is a chlorine atom, a bromine atom or an iodine atom.

R2c-J-Q used for this reaction can be obtained as a commercially available product or can be produced by a known method. Preferred Q is a hydrogen atom or an alkali metal such as sodium or potassium.

The amount of R2c-J-Q used in this reaction is not particularly limited as long as the target reaction proceeds, provided that it is at least one equivalent with respect to the compound represented by formula (6b). When Q is a hydrogen atom, it can also be used as a solvent.

The transition metal used in this reaction may have a ligand, and palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( And triphenyl phosphine) palladium, palladium such as bis (triphenyl phosphine) palladium dichloride, and the like.

The amount of transition metals used in this reaction is usually 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by formula (6b), but is particularly limited as long as the target reaction proceeds It will not be done.

In order to allow the reaction to proceed efficiently, triphenylphosphine, 1,1′-bis (diphenylphosphino) ferrocene, 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl, 2-di-t Phosphine ligands such as -butylphosphino-2'4'6'-triisopropylbiphenyl can be added.

The amount of the phosphine ligand used in this reaction is generally 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (6b), but in particular as long as the target reaction proceeds There is no limitation.

Bases used in this reaction are inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate, and organic bases such as triethylamine, tributylamine and diisopropylethylamine.

The amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds, provided that it is at least 1 equivalent with respect to the compound represented by formula (6b), but usually 1 equivalent It is more than 50 equivalents.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but R2c-JH (wherein, R2c is as defined above, and J is an oxygen atom). Ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane etc., benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene etc. Can be mentioned. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by formula (6b) is there.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually 30 ° C. or more and 200 ° C. or less or the boiling point or less of the solvent.

For post-treatment of the reaction, it is possible to carry out a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by carrying out a filtration operation.

Although the reaction mixture containing the compound represented by Formula (6c) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (6c) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (6c) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method J]

In the formula, R 2 d is a C 1 to C 6 alkyl group which may be optionally substituted with a substituent A, a C 1 to C 6 haloalkyl group, a C 3 to C 8 cycloalkyl group which may be optionally substituted with a substituent A, a substituent A And a C2 to C6 alkenyl group which may be optionally substituted or a C2 to C6 haloalkenyl group, R 2 d-B represents an organoboronic acid, and R 1, R 2 b, X, Y and U 1 are as defined above .

Production method J includes a C1 to C6 alkyl group optionally substituted with substituent A, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group optionally substituted with substituent A, and a substituent A method for obtaining a compound represented by the formula (6d) which is a C2 to C6 alkenyl group which may be optionally substituted by a group A, or a C2 to C6 haloalkenyl group, which is represented by the formula (6b) It is a production method including obtaining by Suzuki-Miyaura coupling in which a compound and an organic boronic acid (R2d-B) are reacted in the presence of a transition metal and a base.

In formula (6b), preferable R2b is a chlorine atom, a bromine atom or an iodine atom.

R2d-B used in this reaction represents an organic boronic acid such as an organic boronic acid or an organic boronic acid ester, and can be obtained as a commercially available product or manufactured by a known method.

The amount of R2d-B used in this reaction is not particularly limited as long as the target reaction proceeds, provided that it is at least 1 equivalent with respect to the compound represented by formula (6b). 1 equivalent or more and 10 equivalents or less.

Transition metals used in this reaction are palladium, nickel, ruthenium and the like, and may have a ligand. Preferably, palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride and the like Palladiums are mentioned.

In order to allow the present reaction to proceed efficiently, phosphine ligands such as triphenylphosphine and tricyclohexylphosphine can be added.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but water solvents, diethyl ether, diisopropyl ether, methyl-t-butyl ether, ethers such as dimethoxyethane, tetrahydrofuran, dioxane, etc. Examples of the solvent include benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents may be used alone or in combination of two or more in any proportion.

Although the reaction mixture containing the compound represented by Formula (6d) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (6d) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (6d) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method K]

In the formula, R 2 e represents a C 2 to C 6 alkynyl group which may be optionally substituted with a substituent A, or a C 2 to C 6 haloalkynyl group, and R 1, R 2 b, X, Y and U 1 are as defined above.

Production method K is a method for obtaining a compound represented by the formula (6e) in which R2e is a C2 to C6 alkynyl group optionally substituted with a substituent A, or a C2 to C6 haloalkynyl group, It is a manufacturing method including obtaining by the Sonogashira coupling in which the compound represented by (6b) and a terminal alkyne compound are reacted in the presence of a transition metal and a base.

The terminal alkyne compound used for this reaction can be obtained as a commercially available product or can be produced by a known method. Also, trimethylsilylacetylene can be used as a terminal alkyne compound. In this case, it is necessary to carry out desilylation after introducing a trimethylsilylethynyl group into the compound represented by the formula (6b). For desilylation, Journal of the American Chemical Society, Volume 131, No. 2, pages 634-643 (2009). And Journal of Organometallic Chemistry, Vol. 696, No. 25, pp. 4039-4045 (2011). Etc. can be referred to.

The amount of the terminal alkyne compound to be used in this reaction is not particularly limited as long as the target reaction proceeds, provided that it is at least 1 equivalent with respect to the compound represented by formula (6b). 1 to 10 equivalents.

The transition metal used in this reaction may have a ligand, and palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( And triphenyl phosphine) palladium, palladium such as bis (triphenyl phosphine) palladium dichloride, and the like. In addition, coppers such as copper chloride, copper bromide and copper iodide are also used at the same time.

The amount of transition metals used in this reaction is usually 0.001 equivalents or more with respect to the compound represented by the formula (6b) with each of palladium and the like, and the target reaction is There is no particular limitation as far as it progresses. The preferred amounts are both 0.001 to 1 equivalent.

Examples of the base used in this reaction include organic amines such as triethylamine, tributylamine, isopropylamine, diethylamine, diisopropylamine and diisopropylethylamine, and inorganic bases such as sodium carbonate, potassium carbonate and cesium carbonate.

The amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds, provided that it is at least 1 equivalent with respect to the compound represented by formula (6b), but usually 1 equivalent It is more than 50 equivalents. In addition, as to the organic base in liquid form, it can be used as a solvent.

In order to allow the reaction to proceed efficiently, phosphine ligands such as tri-t-butylphosphine and 2-dicyclohexylphosphino-2'4'6'-triisopropylbiphenyl can be added, but it is not essential. .

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, nitrile solvents such as acetonitrile, N-methylpyrrolidone, N, N-dimethylformamide Amide solvents such as N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, triethylamine, Butylamine, isopropylamine, diethylamine, diisopropylamine, organic amine solvents such as diisopropylethylamine. These solvents may be used alone or in combination of two or more in any proportion.

For post-treatment of the reaction, it is possible to carry out a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. These solvents may be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield. It is also possible, but not essential, to remove insolubles by carrying out a filtration operation.

Although the reaction mixture containing the compound represented by Formula (6e) obtained above can remove moisture with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (6e) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (6e) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method L]

In the formula, U2 represents a halogen atom, and HalR, R1, R2, X and Y are as defined above.

Production method L is a method for obtaining a compound represented by the formula (6f) in which U 2 is a halogen atom, and represented by the formula (6-1) using a radical initiator and a halogenating agent (HalR) A method of production comprising reacting a compound.

In formula (6f), preferred U2 is a chlorine atom, a bromine atom or an iodine atom.

Examples of the radical initiator used in this reaction include azobisisobutyronitrile, benzoyl peroxide and the like.

The amount of the radical initiator used for this reaction is not particularly limited as long as the target reaction proceeds, but generally 0.01 equivalent to the compound represented by the formula (6-1) More than 1.0 equivalent.

The halogenating agent used in this reaction is N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin And 1,3-diiodo-5,5-dimethylhydantoin.

The amount of the halogenating agent used in this reaction is not particularly limited as long as the target reaction proceeds, provided that the amount is 2 equivalents or more with respect to the compound represented by formula (6-1). Usually, it is 2 equivalents or more and 2.8 equivalents or less.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 times by weight or more and 200 times by weight the compound represented by the formula (6-1) It is below.

Although the reaction mixture containing the compound represented by Formula (6f) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (6f) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (6f) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method M]

In the formula, R 1, R 2, X, Y and U 2 are as defined above.

Production method M is a method for obtaining a compound represented by the formula (6 g) which is a production intermediate of the compound of the present invention, which comprises hydrolyzing a compound represented by the formula (6 f) in the presence of water It is a manufacturing method.

Water is essential for this reaction. In addition, silver nitrate can be used to facilitate the present reaction.

The amount of water used in this reaction is not limited as long as the target reaction proceeds, as long as it is at least 1 equivalent to the compound represented by formula (6f). Water can also be used as a solvent.

The amount of silver nitrate used in this reaction is not limited as long as the target reaction proceeds, provided that the amount is 2 equivalents or more with respect to the compound represented by formula (6f), and usually 2 equivalents or more. It is less than equivalent weight.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but water solvents, diethyl ether, diisopropyl ether, methyl-t-butyl ether, ethers such as dimethoxyethane, tetrahydrofuran, dioxane, etc. A system solvent, nitrile system solvents, such as acetonitrile, etc. are mentioned. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by formula (6f) is there.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually −10 ° C. or more and 100 ° C. or less or the boiling point or less of the solvent.

As post-treatment of the reaction, it is possible to remove undissolved metals by filtration. Furthermore, it is possible to carry out a liquid separation operation by adding water or an appropriate aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. In addition, these solvents can be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield.

Although the reaction mixture containing the compound represented by Formula (6g) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (6 g) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (6 g) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method N]

In the formulae, R 1, R 2, X, Y and Z are as defined above.

Production method N is a method of obtaining the compound represented by formula (1a) among the compounds represented by formula (1), which comprises a compound represented by formula (6 g) and an organometallic reagent in a solvent It is a manufacturing method including making it react in the inside.

As an organic metal reagent used for this reaction, an organomagnesium halide (Z-Mg-Hal: where Hal represents a halogen atom and Z is as defined above), an organolithium reagent (Z-Li: Here, Z is as defined above), organomagnesium halide-zinc (II) ate complex reagent ([(Z) ₃ -Zn] ^- [Mg-Hal] ⁺ [Mg- (Hal) ₂ ] ₂ : Here, Z and Hal are as defined above, and the like. These organometallic reagents can be obtained as commercially available products or can be produced by known methods.

The amount of the organic metal reagent to be used in this reaction may be 1 equivalent or more with respect to the formula (6 g), and is not particularly limited as long as the target reaction proceeds. Usually, it is 1 equivalent or more and 10 equivalents or less.

The solvent used for the reaction is not particularly limited as long as the target reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc., hexane And hydrocarbon solvents such as heptane, cyclohexane and methylcyclohexane. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by the formula (6 g) is there.

Although the reaction mixture containing the compound represented by Formula (1a) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (1a) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (1a) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method O]

In the formula, R 1, R 2, R 8 a, X, Y and Z are as defined above.

Production method O is a method for obtaining a compound represented by formula (1b) among compounds represented by formula (1), wherein the compound represented by formula (1a) and an ortho ester are A method of production comprising reacting in the presence of a solvent.

The orthoesters used in this reaction are preferably orthoformates, and can be obtained as commercially available products or can be produced by known methods.

The amount of ortho esters used in this reaction may be at least 1 equivalent with respect to the compound represented by formula (1a), and is not particularly limited as long as the target reaction proceeds, 1 equivalent or more and 10 equivalents or less.

In order to allow the reaction to proceed smoothly, the alcohol represented by R8aOH (R8a is as defined above) can be added, and can also be used as a solvent.

The amount of alcohol used represented by R8aOH (R8a is as defined above) used in this reaction is not particularly limited as long as the target reaction proceeds, but in general, it is represented by the formula (1a) It is 50 or less equivalent with respect to the compound represented, and is not essential.

Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as trifluoroacetic acid, methanesulfonic acid, p-toluenesulfonic acid and trifluoromethanesulfonic acid.

The amount of the acid used in this reaction is not particularly limited as long as the target reaction proceeds, provided that it is 0.01 equivalent or more with respect to the compound represented by formula (1a). 0.01 equivalent or more and 20 equivalents or less.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but the alcohol solvents represented by R8aOH (R8a has the same meaning as described above), such as nitromethane and nitrobenzene Examples thereof include nitro solvents, halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents may be used alone or in combination of two or more in any proportion.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by Formula (1a). is there.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually −30 ° C. or more and 100 ° C. or less or the boiling point or less of the solvent.

For post-treatment of the reaction, it is possible to carry out a liquid separation operation by adding water or a suitable aqueous solution to the reaction mixture. When using an aqueous solution, an acidic aqueous solution in which hydrochloric acid, sulfuric acid, ammonium chloride or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, sodium hydrogencarbonate or the like is dissolved, thiosulfuric acid An aqueous solution or a saline solution in which a salt containing a sulfur atom such as sodium or sodium sulfite is dissolved can be optionally used. At the time of liquid separation operation, benzene solvents such as toluene, xylene, benzene, chlorobenzene and dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate and butyl acetate, diethyl ether, diisopropyl ether, methyl Ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride etc., solvents not compatible with water such as hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane It is possible to add. These solvents may be used alone or in combination of two or more in any proportion. The number of times of liquid separation is not particularly limited, and the separation can be carried out according to the desired purity and yield.

Although the reaction mixture containing the compound represented by Formula (1b) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (1b) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (1b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method P]

In the formulae, R 1, R 2, X, Y and Z are as defined above.

Production method P is a method for obtaining the compound represented by formula (1c) among the compounds represented by formula (1), and the compound represented by formula (1a) and the fluorinating agent (FR) Is reacted in a solvent.

(Diethylamino) sulfur trifluoride, bis (2-methoxyethyl) aminosulfur trifluoride, N, N-diethyl-1,1,2,3,3,3-hexafluoropropyl as a fluorinating agent used in this reaction Amines, 2,2-difluoro-1,3-dimethylimidazolidine and the like can be mentioned.

The amount of the fluorinating agent used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1a), and is not particularly limited as long as the target reaction proceeds, 1 equivalent or more and 10 equivalents or less.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, nitrile solvents such as acetonitrile, halogen solvents such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, hexane, heptane, cyclohexane, methylcyclohexane etc Hydrocarbon solvents and the like can be mentioned. These solvents may be used alone or in combination of two or more in any proportion.

Although the reaction mixture containing the compound represented by Formula (1c) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (1c) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (1c) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method Q]

In the formulae, R 1, R 2, X, Y and Z are as defined above.

The production method Q is a method for obtaining the compound represented by the formula (1 d) among the compounds represented by the formula (1), wherein the compound represented by the formula (1 a) and the reducing agent Below, it is a manufacturing method including making it react in a solvent.

As a reducing agent used for this reaction, triethylsilane, sodium borohydride and the like can be mentioned.

The amount of the reducing agent used in this reaction is not particularly limited as long as the target reaction proceeds, as long as the amount of the reducing agent used is 1 equivalent or more with respect to the compound represented by formula (1a). More than 20 equivalents or less.

Examples of the acid used in this reaction include trifluoroacetic acid, boron trifluoride diethyl ether complex, trifluoromethanesulfonic acid, trimethylsilyl trifluoromethanesulfonate, aluminum chloride and the like.

The amount of the acid used in this reaction may be at least 1 equivalent with respect to the compound represented by formula (1a), and is not particularly limited as long as the target reaction proceeds, but usually 1 It is equal to or more than 50 equivalents. When the acid is a solution, it can be used as a solvent.

The solvent used for this reaction is not particularly limited as long as the target reaction proceeds, but an acidic solvent such as trifluoroacetic acid, a halogen based solvent such as dichloromethane, dichloroethane, chloroform, carbon tetrachloride, etc. Ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane and the like can be mentioned. These solvents may be used alone or in combination of two or more in any proportion.

The temperature at which this reaction is carried out is not particularly limited as long as the target reaction proceeds, but it is usually −10 ° C. or more and 150 ° C. or less or the boiling point or less of the solvent.

Although the reaction mixture containing the compound represented by Formula (1d) obtained above can remove water with desiccants, such as sodium sulfate and magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (1d) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (1d) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

[Manufacturing method R]

In the formula, Hal R, R 1, R 2, X, Y and U 2 are as defined above.

Production method L is a method for obtaining a compound represented by the formula (6h) in which U2 is a halogen atom, and represented by the formula (6-1) using a radical initiator and a halogenating agent (HalR) A method of production comprising reacting a compound.

In formula (6h), preferred U2 is a chlorine atom, a bromine atom or an iodine atom.

The amount of the halogenating agent used in this reaction is not particularly limited as long as the target reaction proceeds, provided that the amount is 1 equivalent or more with respect to the compound represented by formula (6-1). Usually, it is 1 equivalent or more and 1.5 equivalents or less.

Production method R can be carried out according to production method L by changing the amount of the halogenating agent in production method L as described above.

[Manufacturing method S]

In the formula, G32, G33, G34, and G35 are each independently a carbon atom or a nitrogen atom, nm is an integer of 0 to 4 (in the case where nm is 2 or more, R4 of 2 or more substitution is each R 1 represents an independent substituent, which may be the same or different and may be optionally selected), and R 1, R 2, R 4, X, Y and U 2 are as defined above.

Production method S is a method of obtaining a compound represented by the formula (1e), which comprises the compound represented by the formula (6h) and the compound represented by the formula (7) in a solvent in the presence of a base It is a manufacturing method including making it react.

The compound represented by Formula (7) used for this reaction can be obtained as a commercial item, or can be manufactured by a well-known method.

When the compound represented by the formula (7) used in the present reaction forms a salt with an acidic substance such as hydrochloric acid or sulfuric acid, the amine may be used after desalting by a known method it can. In addition, the amine salt can be used as it is in the present reaction by adding one or more equivalents of a base to the acidic substance forming a salt.

The amount of the compound represented by the formula (7) used in this reaction may be at least 1 equivalent or more with respect to the compound represented by the formula (6h), and is particularly limited as long as the target reaction proceeds. Although it does not happen, it is usually 1 equivalent or more and 10 equivalents or less.

Inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate and sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, lutidine etc. as the base used in this reaction Although the class is illustrated, it is not particularly limited as long as the target reaction proceeds.

The amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by the formula (6h), and is not particularly limited as long as the target reaction proceeds, but usually 1 It is equal to or more than 20 equivalents. Moreover, when using the compound represented by Formula (7) which formed the salt with an acidic substance, preferable amount is 2 to 20 equivalent normally.

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but generally, it is 3 to 200 times by weight the amount of the compound represented by formula (6h) is there.

Although the reaction mixture containing the compound represented by Formula (1e) obtained above can remove water with a desiccant such as sodium sulfate or magnesium sulfate, it is not essential.

The reaction mixture containing the compound represented by the formula (1e) obtained above can be distilled off under reduced pressure as long as the compound does not decompose.

The reaction mixture containing the compound represented by the formula (1e) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography and the like using an appropriate solvent. It may be appropriately set according to the target purity.

The compounds represented by the formula (1) can be produced by arbitrarily combining the production methods A to S shown above. Alternatively, the compound represented by the formula (1) can be produced by any combination of known methods and production methods A to S.

The compounds of the present invention can be used as pesticides because they can control organisms harmful to plants. Specifically, fungicides, insecticides, herbicides, plant growth regulators and the like can be mentioned. Preferably, it is a microbicide.

The compounds of the present invention can be used as agricultural and horticultural fungicides in upland fields, paddy fields, tea gardens, orchards, meadows, lawns, forests, gardens, street trees, etc. for controlling plant diseases.

The plant diseases referred to in the present invention refer to plants with crops such as flowers, flowers, trees and trees, withered, withered, yellowed, atrophied, and general abnormal pathological symptoms such as acupuncture, or spots, withered leaves, mosaics Partial pathological symptoms such as cigars, dead leaves, root rot, root bumps and bumps are caused. That is to say, plants become ill. Pathogens that cause plant diseases mainly include fungi, bacteria, spiroplasmas, phytoplasmas, viruses, viroids, parasitic higher plants, nematodes and the like. The compounds of the present invention are effective against fungi but are not limited thereto.

The diseases caused by fungi are mainly fungal diseases. Fungi (fungi) which cause fungal diseases include Neisseria gonorrhoeae, oomycetes, zygomycetes, ascomycetes, basidiomycetes and imperfect fungi. For example, root-knot fungus, root-knot disease powdery mildew fungus, sugar beet root-knot disease fungus, as egg fungus, downy mildew fungus, Pythium spp., Aphanomyces spp., Rhizopus spp. Phytophthora infestans, corn leaf blight fungus, rice blast fungus, powdery mildew, powdery mildew, anthracnose fungus, scab fungus, scab fungus, scab fungus, scab fungus, rust basidiomycetes as basidiomycetes, scab fungus, purple crest Examples include downy mildew, blast fungus, sheath blight fungus, gray mold fungus as incomplete fungus, Alternaria sp., Alternaria sp., Fusarium sp., Penicillium sp., Rhizoctonia sp.

The compounds of the present invention are effective against various plant diseases. Below, the specific example of a disease name and its pathogen name is shown.

Rice blast disease (Magnaporthe grisea), sheath blight (Thanatophorus cucumeris), brown blight (Ceratobasidium setariae), brown blight blight (Wateea circinata), brown blight (Thanatephorus cucumeris), scab mildew Sclerotium hydrophilum, red blight (Wairea circinata), black rot (Entyloma dactylidis), micrococcal disease (Magnaporthe salvinii), gray blight (Ceratobasidium cornigerum), sesame leaf blight (Cochliobolus miyabeanus), leaf leaf Blight disease (Sphaerulina oryzina , Scabies (Gibberella fujikuroi), seedling blight (Pythium spp., Fusarium spp., Trichoderma spp., Rhizopus spp., Rhizoctonia solani, Mucor sp., Phoma sp.), Seedling rot (Pythium spp., (Achlya spp., Dictyuchus spp.), Rice scab (Claviceps virens), black scion (Tilletia barclayana), brown rice (Curvularia spp., Alternaria spp.), Yellow dwarf disease (Sclerophthora macrospora), white leaf blight ( Xanthomonas oryzae pv. Oryzae), brown stripe disease (Acidovora) avenae subsp. avenae), internal blanching disease (Erwinia ananas), seedling blight (Burkholderia plantarii), leaf blight (Burkholderia glumae), leaf sheath browning disease (Pseudomonas fuscovaginae), blight blight (Pseudomonas syringae pv. oryzae), stock rot (Erwinia chrysanthemi), yellow dwarf (Phytoplasma oryzae), rice leaf blight (Rice stripe tenuivirus), dwarf (Rice dwarf reovirus);
Powdery mildew of wheat (Blumeria graminis f. Sp. Hordei; f. Sp. Tritici), rust (Puccinia striiformis, Puccinia graminis, Puccinia recondita, Puccinia hordei), macular disease (Pyrenophora graminea), web spot disease Pyrenophora teres), Fusarium head blight (Gibberella zeae, Fusarium culmorum, Fusarium avenaceum, Monographella nivalis), snow blight (Typhula incarnata, Typhula ishikariensis, Monographella nivalis), naked scab (Ustilag) nuda), scallop (Tilletia caries, Tilletia controversa), scab (Pseudocercosporella herpotrichoides), stock rot (Ceratobasidium gramineum), leaf blight (Rhynchosporium secalis), leaf blight (Septoria tritici), Phaeosphaeria nodorum), seedling blight (Fusarium spp., Pythium spp., Rhizoctonia spp., Septoria spp., Pyrenophora spp.), blight (Gaeumannomyces graminis), anthracnose (Colletotrichum graminicola), Ergot disease (Claviceps purpurea), spotted disease (Cochliobolus sativus), black node disease (Pseudomonas syringae pv. Syringae);
Scab of mildew of corn (Gibberella zeae etc.), seedling blight (Fusarium avenaceum, Penicillium spp., Pythium spp., Rhizoctonia spp.), Rust (Puccinia sorghi), leaf blight of sesame (Cochliobolus heterostrophus), scab (Ustilago maydis), anthracnose (Colletotrichum graminicola), northern spot disease (Cochliobolus carbonum), brown streak disease (Acidovorax avenae subsp. Avenae), streak fungus disease (Burkholderia andropogonis), lodging bacterial disease (Erwinia chrysanthemi pv. Zea Bacteriostatic blight (Erwinia stewartii); grape downy mildew (Plasmoparaviticola), rust (Physopella ampelopsidis), powdery mildew (Uncinula necator), black rot (Elsinoe ampelina), late rot (Glomerella cingulata) , Colletotrichum acutatum), black rot (Guignardia bidwellii), spiny mildew (Phomopsis viticola), soot blight (Zygophiala jamaicensis), gray mold (Botrytis cinerea), blast blight (Diaporthe medusaea), purple root rot ( Helicobasidium mompa), white crest Disease (Rosellinia necatrix), root-head cancer disease (Agrobacterium vitis); apple powdery mildew (Podosphaera leucotricha), scab disease (Venturia inaequalis), spotted leaf disease (Alternaria mali), scab disease (Gymnosporangium yamadae), Monilia Disease (Monilinia mali), rot disease (Valsa ceratosperma), ring disease (Botryosphaeria berengeriana), anthracnose (Colletotrichum acutatum, Glomerella cingulata), soot blight disease (Zygophiala jamaicensis), scab disease (Gloeodes pomi) ena), Mycosphaerella pomi, Helicobasidium mompa, White scab (Rosellinia necatrix), Blight blight (Phomopsis mali, Diaporthe tanakae), brown blight (Diplocarpon mali), apple fire Disease (Erwinia amylovora), root head cancer disease (Agrobacterium tumefaciens), hair root disease (Agrobacterium rhizogenes);
Black spot of pear (Alternaria kikuchiana), star blight (Venturia nashicola), red star (Gymnosporangium asiaticum), ring blight (Botryosphaeria berengeriana f. Sp. Piricola), blight blight (Phomopsis fukushii), blight of blight Erwinia sp.), Root-head cancer disease (Agrobacterium tumefaciens), rust blight (Erwinia chrysanthemi pv. Chrysanthemi), flower rot bacteriobacteria (Pseudomonas syringae pv. Syringae); s ringae), blight of blight (Erwinia sp.); peach scab (Cladosporium carpophilum), homoposis rot (Phomopsis sp.), plague (Phytophthora sp.), anthracnose (Colletotrichum gloeosporioides), leaf rot (Taphrina) Deforans), Perforating Bacterial Disease (Xhanthomonas campestris pv. pruni), Root Head Onset Disease (Agrobacterium tumefaciens); Sweet Potato Anthracnose (Glomerella cingulata), Fungal Fungus Nervosa (Monilinia kusanoi), Grizzly Disease (Monilinia fructicola ), Root-head cancer disease (Agrobacter um tumefaciens), resinous bacterial disease (Pseudomonas syringae pv. syringae); Anthrax (Glomerella cingulata) of oyster (Geromerella cingulata), deciduous disease (Cercospora kaki; Mycosphaerella nawae), powdery mildew (Phyllactinia kakikora), Nematode cancer disease (Agrobacterium Tumefaciens); Citrus black spot (Diaporthe citri), green mold (Penicillium digitatum), blue mold (Penicillium italicum), scab (Elsinoe fawcettii), brown rot (Phytophthora citrophthora), scab (Xhanth) omonas campestris pv. citri), Pseudomonas syringae pv. syringae, greening disease (Liberibactor asiaticus), rhizo oncosis (Agrobacterium tumefaciens);
Tomato, cucumber, beans, strawberry, potato, cabbage, eggplant, lettuce etc. Botrytis cinerea; tomato, cucumber, beans, strawberry, potato, rapeseed, cabbage, eggplant, lettuce, etc. sclerotinia sclerotiorum ); Seedling blight of various vegetables such as tomato, cucumber, beans, radish, watermelon, eggplant, rapeseed, pepper, spinach, sugar beet etc. (Rhizoctonia spp., Pythium spp., Fusarium spp., Phythophthora spp., Sclerotinia sclerotirum etc.) Blight of solanaceous plant (Ralstonia solanacearum); downy mildew (Pseudoperonospora cubens) s), powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotrichum orbiculare), vine blight (Didymella bryoniae), scab (Fusarium oxysporum), blight (Phytophthora parasitica, Phytophthora melonitis, Phitichitithithelium Etc.), brown spot bacterial disease (Xhanthomonas campestris pv. Cucurbitae), soft rot (Erwinia carotovora subsp. Carotovora), spotted bacterial disease (Pseudomonas syri) ... Gae pv lachrymans), edges bacterial grain rot (Pseudomonas marginalis pv marginalis), temple petitioner disease (Streptomyces sp), root disease (Agrobacterium rhizogenes), cucumber mosaic virus (Cucumber mosaic virus);
Ring blight (Alternaria solani), leaf blight (Fulvia fulva), plague (Phytophthora infestans), wilt (Fusarium oxysporum), root rot (Pythium myriotylum, Pythium dissotocum), anthracnose (Colletotrichum gloeoporiodes) Disease (Clavibacter michiganensis), stem blight disease (Pseudomonas corrugata), black spot bacterial disease (Pseudomonas viridiflava), soft rot (Erwinia carotovora subsp. Carotovora), leaf blight (Crynebacterium sp.), Yellow wilt (P ytoplasma asteris), yellow leaf atrophy (Tobacco leaf curl subgroup III geminivirus); powdery mildew of eggplant (Sphaerotheca fuliginea etc.), slime blight (Mycovellosiella nattrassii), plague (Phytophthora infestans), brown rot (Phytophthora capsici) Brown spot bacterial disease (Pseudomonas cichorii), stem blight bacterial disease (Pseudomonas corrugata), stem rot bacterial disease (Erwinia chrysanthemi), soft rot (Erwinia carotovora subsp. Carotovora), spotted bacterial disease (Pseudomonas sp.); Black spot (Alternaria brassicae), black rot (Xhanthomonas campestris pv. Campestris), black spot blight (Pseudomonas syringae pv. Maculicola), soft rot (Erwinia carotovora); black spot of Brassicaceae (Alternaria brassicae) Etc.), white spot (Cercosporella brassicae), root blight (Phoma lingam), root scab (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), black rot (Xhanthomonas campestris pv. Campestris), black spot bacterial disease Pseudomonas sy ringae pv. maculicola), soft rot (Erwinia carotovora subsp. carotovora);
Strains of rot of cabbage (Thanatephorus cucumeris), yellow rot (Fusarium oxysporum), black scab (Alternaria brassisicola); Chinese cabbage end rot (Rhizoctonia solani), yellow rot (Verticillium dahliae); Allium rust (Puccinia allii) ), Black rot (Alternaria porri), white scab (Sclerotium rolfsii), white rot (Phytophthora porri), black rot fungus (Sclerotium cepivorum); onion scab (Curtobacterium flaccumfaciens), soft rot (Erwinia carotovora subsp) . Carot vora), spotted bacterial disease (Pseudomonas syringae pv. syringae), rot (Erwinia rhapontici), scaly rot (Burkholderia gladioli), yellow rot (Phytoplasma asteris); soft rot (Erwinia carotovora subsp. carotovora) of garlic Disease (Pseudomonas marginalis pv. Marginalis); purpura of soybean (Cercospora kikuchii), mildew (Elsinoe glycines), black spot (Diaporthe phaseolorum), rhizoctonia root rot (Rhizoctonia solani), stem blight (Phytophthora soj) e) downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi), anthracnose (Colletotrichum truncatum etc.), leaf blight (Xhanthomonas campestris pv. glycines), spotted blight (Pseudomonas syringae pv. glycinea); Anthracnose (Colletotrichum lindemuthianum), bacterial blight (Ralstonia solanacearum), scab (Pseudomonas syringae pv. Phaseolicola), brown leaf blight (Pseudomonas viridiflava), leaf blight (Xhanthomonas campestris p . phaseoli);
Groundnut (Mycosphaerella berkeleyi), brown spot (Mycosphaerella arachidis), blight (Ralstonia solanacearum); powdery mildew (Erysiphe pisi) of pea, downy mildew (Peronospora pisi), vine blight (Pseudomonas) syringae pv. pisi), scab disease (Xhanthomonas campestris pv. pisi; downy mildew (Peronospora viciae), plague (Phytophthora nicotianae); Plague (Phyt phthora infestans), silver blight (Helminthosporium solani), dry rot (Fusarium oxysporum, Fusarium solani), powdery mildew (Spongospora subterranea), blight (Ralstonia solanacearum), scab (Erwinia carotovora subsp. atticeptica) ), Scab disease (Streptomyces scabies, Streptomyces acidiscabies), soft rot (Erwinia carotovora subsp. Carotovora), viscous rot (Crostridium spp.), Ring rot (Clavobacter michiganensis sub) sp. sepedonicus); sweet potato blight (Streptomyces ipomoeae); sugar beet (Cercospora beticola), downy mildew (Peronospora schachtii), black root disease (Aphanomyces cochioides), snake eye disease (Phoma betae), rooted head Cancer disease (Agrobacterium tumefaciens), scab disease (Streptomyces scabies), spotted bacterial disease (Pseudomonas syringae pv. Aptata);
Black leaf blight of carrot (Alternaria dauci), gall disease (Rhizobacter dauci), rhizocarp disease (Agrobacterium tumefaciens), Streptomyces scabies (Streptomyces spp.), Soft rot (Erwinia carotovora subsp. Carotovora); Powdery mildew of strawberries (Sphaerotheca aphanis var. Aphanis), plague (Phytophthora nicotianae etc.), anthracnose (Glomerella cingulata etc.), fruit rot (Pythium ultimum), blight (Ralstonia solanacearum), horny mildew (Xhanthomonas) campestris), Bacterial mildew (Pseudomonas marginalis pv. Marginalis); Tea scab (Exobasidium reticulatum), white scab (Elsinoe leucospila), anthracnose (Colletotrichum theae-sinensis), rot blotch (Pestalotiopsis longiseta), fire blight (Pseudomonas) Theae), scab (Xhanthomonas campestris pv. theicola), scabies (Pseudomonas sp.); tobacco scab (Alternaria alternata), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotritri) hum gloeosporioides), plague (Phytophthora nicotianae), wild blight (Pseudomonas syringae pv. tabaci), yellow blight (Pseudomonas syringae pv. mellea), cavity disease (Erwinia carotovora subsp. carotovora), dead blight (Ral , Tobacco mosaic virus (Tobacco mosaic virus);
Coffee rust (Hemileia vastatrix); Banana black shigatogas (Mycosphaerella fijiensis), Panama disease (Fusarium oxysporum f. Sp cubense); Cotton blight (Fusarium oxysporum), mildew (Ramularia areola); Sclerotinia sclerotiorum, scab disease (Xhanthomonas campestris pv. Malvacearum), cavity disease (Erwinia carotovora subsp. Carotovora), spotted blight disease (Pseudomonas syringae pv. Helianthi); Mildew (Sphaerotheca pannosa etc.), plague (Phytophthora megasperma), downy mildew (Peronospora sparsa), rhizo oncosis (Agrobacterium tumefaciens); brown spot of chrysanthemum (Septoria obesa), white rust (Puccinia horiana) ), Plague (Phytophthora cactorum), spotted bacterial disease (Pseudomonas cichorii), soft rot (Erwinia carotovora subsp. Carotovora), root head cancer disease (Agrobacterium tumefaciens), hair root disease (Agrobacterium rhizogenes), green disease (auPhythma histoplasma) ifolia); brown patch disease (Rhizoctonia solani), duller spot disease (Sclerotinia homoeocarpa), carbularia leaf blight (Curvularia sp.), rust (Puccinia zoysiae), hermintosporium leaf blight (Cochliobolus sp.) , Cloud disease (Rhynchosporium secalis), Damping disease (Gaeumannomyces graminis), Anthracnose (Colletotrichum sp.), Snow rot brown powdery mildew (Typhula incarnata), Snow rot black powdery mildew (Typhula ishikariensis), snow rot Large-scale fungal sclerotis disease (Myriosclerotinia borealis), fairy ring disease Marasmius Oreades etc.), Pythium disease (Pythium aphanidermatum, etc.), blast (Pyricularia grisea), and the like.

The compound of the present invention may be used alone, but preferably it is mixed with a solid carrier, liquid carrier, gas carrier, surfactant, fixing agent, dispersing agent, stabilizer, etc., dusting agent, wettable agent The composition can be used as a composition such as water dispersible granules, water solvents, granules water solvents, granules, emulsions, solutions, microemulsions, aqueous suspensions, aqueous emulsions, suspoemulsions and the like. There is no limitation to those compositions as long as the effect is exhibited.

Specific formulation examples are shown below, but are not limited thereto.

[Formulation example 1 flowable]
The compound of the present invention (10 parts by mass), sodium salt of formaldehyde condensate of naphthalenesulfonic acid (5 parts by mass), polyoxyethylene arylphenyl ether (1 parts by mass), propylene glycol (5 parts by mass), silicone antifoam ( 0.1 parts by mass), xanthan gum (0.2 parts by mass), and ion-exchanged water (78.7 parts by mass) to form a slurry, and further wet grinding using glass beads having a diameter of 1.0 mm with Dinomill KDL Obtain a flowable agent.

Formulation Example 2 Emulsion
The compound of the present invention (5 parts by mass) is dissolved in a mixed solution of xylene (40 parts by mass) and cyclohexane (35 parts by mass), and Tween 20 (20 parts by mass) is added to and mixed with this solution to obtain an emulsion.

[Formulation Example 3 Wettable powder]
The compound of the present invention (10 parts by mass), white carbon (10 parts by mass), polyvinyl alcohol (2 parts by mass), dioctyl sulfosuccinate sodium salt (0.5 parts by mass), alkylbenzenesulfonic acid sodium salt (5 parts by mass), calcined Diatomaceous earth (10 parts by mass) and kaolinite clay (62.5 parts by mass) are thoroughly mixed and ground in an air mill to obtain a wettable powder.

Hereinafter, application of the composition of the present invention (pest control agent for agriculture and horticulture, fungicide for agriculture and horticulture) will be described.

As a method of applying the composition containing the compound of the present invention, a method of contacting with a plant or a seed, or a method of including it in cultivation soil and contacting with a root or a rhizome of a plant can be mentioned. As a specific example, foliage spraying treatment to individual plants, injection treatment, seedling box treatment, cell tray treatment, spraying treatment to plant seeds, spraying treatment to plant seeds, immersion treatment to plant seeds, immersion treatment to plant seeds, plant seeds Dressing treatment, spraying treatment on soil surface, mixing with soil after spraying treatment on soil surface, pouring treatment into soil, pouring treatment in soil, soil blending after injection treatment, soil irrigation treatment, soil irrigation treatment Soil mixing etc. are mentioned. In general, any application method as used by those skilled in the art exerts sufficient efficacy.

The term "plant" as used in the present invention refers to those that live without exercise by performing photosynthesis. As a specific example, rice, wheat, barley, corn, coffee, banana, grape, apple, pear, peach, sweet potato, oyster, citrus, soybean, green bean, cotton, strawberry, potato, cabbage, lettuce, tomato, cucumber, eggplant, Watermelon, sugar beet, spinach, green peas, pumpkin, sugar cane, tobacco, pepper, sweet potato, sweet potato, taro, konjac, cotton, sunflower, rose, tulip, chrysanthemum and the like, and F1 varieties thereof, and the like. In addition, it also includes genetically modified crops that are produced by artificially manipulating genes etc. and are not naturally present in the natural world, and examples include herbicide resistant soybean, corn, cotton, etc. rice adapted to cold areas And tobacco, agricultural and horticultural crops such as corn and cotton to which an insecticidal substance producing ability has been imparted. Furthermore, trees such as pine, ash, ginkgo, maple, oak, poplar, zelkova, etc. may be mentioned. The term "plant" as used in the present invention is a generic term for all parts constituting the individual plant, and includes, for example, stems, leaves, roots, seeds, flowers, fruits and the like.

The term "seed" as used in the present invention refers to one which stores nutrients for sprouting young plants and is used for agricultural propagation. Specific examples include corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, spiny pea, squash, sugar cane, tobacco, green pepper, Brassica napus seeds, F1 varieties thereof, etc. Examples thereof include seeds, seeds such as taro, potato, sweet potato, konjac, edible lilies, bulbs such as tulip, seeds such as raccoon, and seeds and tubers of genetically modified crops.

The application rate and application concentration of the composition containing the compound of the present invention vary depending on the target crop, target disease, degree of disease occurrence, dosage form of the compound, application method and various environmental conditions, etc. The amount of active ingredient is suitably from 0.1 to 10,000 g per hectare, preferably from 10 to 1,000 g per hectare. In the case of seed treatment, the amount used is from 0.0001 to 1000 g, preferably from 0.001 to 100 g, per kg of seed as the amount of the active ingredient. When the composition containing the compound of the present invention is used as foliage application to individual plants, application to soil surface, injection into soil, or soil irrigation, it is diluted to an appropriate concentration in an appropriate carrier. You may process afterward. When the composition containing the compound of the present invention is brought into contact with plant seeds, the plant seeds may be used after being diluted to an appropriate concentration and then subjected to dipping, dressing, spraying or smearing. The amount of the composition used for immersion, dusting, spraying or smearing treatment is usually about 0.05 to 50% of the weight of the dry plant seed, preferably 0.1 to 30%, as the amount of the active ingredient. Although it is suitable, it may be suitably set according to the form of the composition and the kind of the plant seed to be treated, and it is not limited to these ranges.

The compound of the present invention may be, if necessary, other pesticides, for example, pesticides such as fungicides, insecticides (including acaricides and nematocides), herbicides, microbial materials, plant growth regulators and the like, nucleic acids It can be used by mixing it with a disease control agent (WO 2014/062775) as an active ingredient, a soil conditioner or a fertilizer. As a method of mixing and using the compound of the present invention and other agricultural chemicals, a method of using the compound of the present invention and other agricultural chemicals formulated into one dosage form, both formulated into separate dosage forms A method of mixing and using before use, a method of simultaneously using both formulated in separate dosage forms, or using either one of both formulated in separate dosage forms And then use the other method.

Specific components contained in the microbicide which can be used in combination with the compound of the present invention are exemplified in the following group b and include salts, isomers and N-oxides thereof. However, known microbicides are not limited to these.

Group b:
b-1: Phenylamide-based fungicide [b-1.1]: Benalaxyl (benalaxyl), [b-1.2] Benaraxyl M or quaraxyl (benalaxyl-M or kiralaxyl) as a phenylamide-based microbicide, [b -1.3] furanaxyl (furalaxyl), [b-1.4] metalaxyl (metalaxyl), [b-1.5] metalaxyl M or mefenoxam (metalaxyl-M or mefenoxam), [b-1.6] oxadixyl oxadixyl), [b-1.7] ofurace, and the like.

b-2: Mitotic and cell division inhibitors [b-2.1] Benomyl, [b-2.2] carbendazim, [b- as a mitotic and cell division inhibitors 2.3] Fuberidazole (fuberidazole), [b-2.4] thiabendazole (thiabendazole), [b-2.5] thiophanate (thiophanate), [b-2.6] thiophanate methyl (thiophanate-methyl), [b- 2.7] Dietophencarb (dithofencarb), [b-2, 8] Zoxamide (zoxamide), [b-2.9] Etaboxam (ethaboxam), [b-2. 10] Pencicuron (pencycuron), [b-2. 11] Fluopico Examples thereof include fluopicolide, [b-2.12] phenamacril and the like.

b-3: Succinic acid dehydrogenase inhibitor (SDHI agent)
[B-3.1] Benodanil (benodanil), [b-3.2] benzobindiflupyr (benzavindiflupyr), [b-3.3] bixafen (bixafen) as a succinate dehydrogenase inhibitor (SDHI agent) ), [B-3.4] boscalid, [b-3.5] carboxin, [b-3.6] fenfuram, [b-3.7] fluopyram [B-3.8] flutolanil, [b-3.9] fluxapyroxad, [b-3. 10] frametpyr, [b-3. 11] isofetamide ), [B-3.12] isopyrazam (isop) razam), [b-3.13] mepronil (mepronil), [b-3. 14] oxycarboxin, [b-3. 15] penthiopyrad, [b-3. 16] penflufen ( penflufen), [b-3.17] pydiflumetofen, [b-3. 18] sedaxane, [b-3. 19] thifluzamide, [b-3. 20] pyradiflumid (Pyraziflumid) and the like.

b-4: external quinone inhibitor (QoI agent)
As a quinone external inhibitor (QoI agent), [b-4.1] azoxystrobin (azoxystrobin), [b-4.2] coxoxystrobin (coumoxystrobin), [b-4.3] dimoxyst Robin (dimoxystrobin), [b-4.4] enoxastrobin (enoxastrobin), [b-4.5] famoxadone (famoxadone), [b-4.6] fenamidone (fenamidone), [b-4.7] ] Phenaminst robin (fenaminstrobin), [b-4.8] fluphenoxystrobin (flufenoxystrobin), [b-4.9] fluoxastrobin (fluoxastrobin), [b-4. 10] kresoxim-methyl (kresoxim-me hyl), [b-4.11] mandestrobin, [b-4. 12] metominostrobin, [b-4. 13] orysastrobin, [b-4. 14] Picoxystrobin, [b-4.15] pyraclostrobin, [b-4. 16] pyrametostrobin, [b-4. 17] pyraoxystrobin [B-4.18] pyribencarb, [b-4. 19] triclopyricarb, [b-4. 20] trifloxystrobin (trifloxyst) obin), and the like.

b-5: internal quinone inhibitor (QiI agent)
Examples of the quinone internal inhibitor (QiI agent) include [b-5.1] cyazofamide (cyazofamid), [b-5.2] amisulbrom and the like.

b-6: Oxidative phosphorylation uncoupling inhibitor As an oxidative phosphorylation uncoupling inhibitor, [b-6.1] binapacryl (binapacryl), [b-6.2] meptyldinocap, [b-6.2] b-6.3] dinocap (dinocap), [b-6.4] fluazinam, and the like.

b-7: quinone external stigmaterine binding subsite inhibitor (QoSI agent)
Examples of quinone external stigmaterine binding subsite inhibitors (QoSI agents) include [b-7.1] ametoctradin and the like.

b-8: Amino acid biosynthesis inhibitor [b-8.1] Cyprodinil as an amino acid biosynthesis inhibitor, [b-8.2] mepanipyrim (mepanipyrim), [b- 8.3] pyrimethanil (pyrimethanil) Etc.).

b-9: Protein biosynthesis inhibitor [b-9.1] streptomycin as a protein biosynthesis inhibitor, [b-9.2] Blasticidin S (blasticidin-S), [b-9. 3] Kasugamycin (kasugamycin), [b-9.4] oxytetracycline (oxytetracycline) and the like.

b-10: Signal transduction inhibitor [b-10.1] fenpiclonil, [b-10.2] fludioxonil, [b-10.3] quinoxyfen, as a signal transduction inhibitor [B-10.4] proquinazid, [b-10.5] clozolinate (chlozolinate), [b-10.6] dimethaclone (dimethachlone), [b-10.7] iprodione (iprodione), [b-10.4] -10.8] procymidone, [b-10.9] vinclozolin, and the like.

b-11: Lipid and cell membrane biosynthesis inhibitors [b-11.1] Edifenphos (edifenphos), [b-11.2] iprobenphos (iprobenfos), [b-11. Pyrazophos, [b-11.4] isoprothiolane, [b-11.5] biphenyl, [b-11.6] chloroneb, [b-11.7] dichlorane (Dicloran), [b-11.8] quintozene, [b-11.9] tecnazene, [b-11.10] tolclofos-methyl (tolclofos-methyl), [b-11.11] Etridiazole (ec hlomezol or etridiazole), [b-11.12] iodocarb, [b-11. 13] propamocarb, [b-11. 14] prothiocarb, and the like.

b-12: Demethylation inhibitor (DMI agent)
As a demethylation inhibitor (DMI agent), [b-12.1] azaconazole (azaconazole), [b-12.2] bitertanol, [b-12. 3] bromuconazole, [b-12. b-12.4] cyproconazole (cyproconazole), [b-12.5] difenoconazole (difenoconazole), [b-12.6] diniconazole, [b-12.7] diniconazole M (diniconazole-M ), [B-12. 8] epoxiconazole (epoxiconazole), [b-12. 9] etaconazole (etaconazole), [b-12. 10] phenarimol (fenarimol), [b-12. Fenbuconazole (fenbuconazole), [b-12.12] fluquinconazole (fluquinconazole), [b-12. 13] quinconazole (quinconazole), [b-12. 14] flusilazole (flusilazole), [b-12 .15] Flutriaphor (flutriafol), [b-12.16] hexaconazole (hexaconazole), [b-12.17] imazalil (imazalil), [b-12.18] imibenconazole (imibenconazole), [B-12.19] ipconazole (ipconazole), [b-12. 20] metconazole (metconazole), [b-12. 21] microbutanil (myclobutanil [B-12.22] nuarimol (nuarimol), [b-12. 23] oxpoconazole (oxpoconazole), [b-12. 24] oxpoconazole fumarate (oxpoconazole fumarate), [b- 12.25] Pefurazoate, [b-12.26] penconazole, [b-12. 27] prochloraz, [b-12. 28] propiconazole, [b- 12.29] prothioconazole (prothioconazole), [b-12.30] pyriphenox, [b-12. 31] pyrisoxazole, [b-12. 32] Simeconazole (simeconazole), [b-12. 33] tebuconazole (tebuconazole), [b-12. 34] tetraconazole (tetraconazole), [b-12. 35] triadimefon (triadimefon), [b-12. 36] Triadimenol (triadimenol), [b-12. 37] triflumizole (triflumizole), [b-12. 38] triphorine (triforine), [b-12. 39] triticonazole (triticonazole) [b-12 .40] Mefentrifluconazole (mefentrifluconazole), [b-12.41] Ipfentrifluconazole, and the like.

b-13: Aminic fungicide [b-13.1] Aldimorph, [b-13. 2] dodemorph, [b-13. 3] fenpropimorph (fenpropimorph) as an amine bactericidal agent ), [B-13.4] tridemorph (tridemorph), [b-13.5] fenpropidin, [b-13.6] piperaline (piperalin), [b-13.7] spiroxamine (spiroxamine) Etc.).

b-14: 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis [b-14.1] fenhexamid as 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis (Fenhexamid), [b-14.2] fenpyrazamine, and the like.

b-15: squalene epoxidase inhibitor of sterol biosynthesis As a squalene epoxidase inhibitor of sterol biosynthesis, [b-15.1] pyributicarb, [b-15. 2] naftifine, [bftifine] -15.3] Terbinafine (terbinafine) etc. are mentioned.

b-16: Cell wall biosynthesis inhibitor [b-16.1] Polyoxins (polyoxins), [b-16.2] dimethomorph, [b-16.3] flumorph as cell wall biosynthesis inhibitor flumorph), [b-16.4] pyrimorph, [b-16.5] benthiavalicarb, [b-16.6] bentivalaricarb isopropyl, [b-16.6] -16.7] Iprovalicarb (iprovalicarb), [b-16.8] mandipropamide (mandipropamid), [b-17.9] valifenalate (valifenalate), and the like.

b-17: Melanin biosynthesis inhibitor [b-17.1] Phthalide or phthalide, [b-17. 2] Pyroquilone, [b-17. 3] Tricyclazole as a melanin biosynthesis inhibitor (Tricyclazole), [b-17.4] carpropamide, [b-17.5] diclocymet, [b-17.6] phenoxanil, [b-17.7] tolprocarb (tolprocarb) Etc.).

b-18: Host plant resistance inducer [b-18.1] Acibenzolar-S-methyl (acibenzolar-S-methyl), [b-18.2] probenazole (probenazole), [b-18. 1] as a host plant resistance inducer -18.3] Thiazinyl, [b-18.4] Isotianil, [b-18.5] laminarin, and the like.

b-19: dithiocarbamate fungicide [b-19.1] Mancozeb or manzeb as a dithiocarbamate fungicide, [b-19. 2] maneb, [b-19. 3] ] Metilam (metiram), [b-19.4] propineb (propineb), [b-19.5] thiuram (thiram), [b-19.6] zineb (zineb), [b-19.7] ziram (Ziram), [b-19.8] ferbam, and the like.

b-20: Phthalimide fungicide [b-20.1] captan, [b-20.2] captafol, [b-20.3] holpet (folpet) as a phthalimide fungicide And [b-20.4] fluorophorpet and the like.

b-21: guanidine fungicide [b-21.1] guazatine as a guanidine fungicide, [b-21.2] iminoctadine (iminoctadine), [b-21.3] iminoctadine albesylate salt (Iminoctadine albesilate), [b-21.4] iminoctadine triacetate, and the like.

b-22: Multi-functional point contact active germicide [b-22.1] Basic copper chloride, [b-22.2] cupric hydroxide as a multi-functional contact germicidal agent (Copper (II) hydroxide), [b-22.3] basic copper sulfate (copper hydroxide sulfate), [b-22.4] organo copper compound (organocopper compound), [b-22.5] dodecyl benzene sulfone Bisethylenediamine copper complex salt [II] (dodecylbenzene acid sulfonic acid bisethylenediamine copper [II] salt, DBEDC), [b-22.6] sulfur (sulphur), [b-22.7] fluorimide (fluoroim) de), [b-22.8] chlorothalonil, [b-22.9] dichlofluanid (dichlofluanid), [b-22. 10] tolylfluanid (tolylfluanid), [b-22.11] Anilazine (anilazine), [b-22.12] dithianon (dithianon), [b-22. 13] quinomethionate or quinomethionate, [b-22. Can be mentioned.

b-23: Other bactericidal agents [b-23. 1] dichlobentiazox, [b-23.2] fenpicoxamide, [b-23.3] as other bactericidal agents ] Dipimethitron (dipymetitrone), [b-23.4] bupirimate, [b-23.5] dimethyrimol (dimethirimol), [b-23.6] ethylymol (ethirimol), [b-23.7] acetic acid Triphenyltin (fentin acetate), [b-23.8] triphenyltin chloride (fentin chloride), [b-23.9] triphenyltin hydroxide (fentin hydroxide), [b-23.10] oxolinic acid (Oxo linic acid), [b-23.11] hymexazol, [b-23.12] octilinone, [b-23. 13] fosetyl, [b-23. 14] phosphite (Phosphorous acid), [b-23.15] sodium salt of phosphorous acid, [b-23. 16] ammonium salt of phosphorous acid, ammonium phosphate, [b-23. 17] phosphorous Acid potassium salt (potassium phosphate), [b-23.18] tecloftalam, [b-23. 19] triazoloxide, [b-23. 20] flusulfamide (flusulfamide) [B-23.21] diclomezine, [b-23. 22] silthiofam (silthiofam), [b-23. 23] diflumetrim, [b-23. 24] methasulfocarb, [B-23.25] cyflufenamide (cyflufenamid), [b-23.26] metrafenone (metrafenone), [b-23. 27] pyriofenone, [b-23.28] dodine, [b -23.29] flutianil (flutianil), [b-23.30] ferrimzone (ferimzone), [b-23.31] oxathiapiprolin (oxathiapiprolin), [b-23. 32] tebufloquin (tebufloquin), [b-23.33] picalbutrazox (picarbutrazox), [b-23.34] validamycins (validamycins), [b-23.35] shimoxanyl (cymoxanil), [b- 23.36] quinofumelin,

[B-23.37] Formula (s1)

A compound represented by (see WO 98/046607),

[B-23.38] Formula (s2)

A compound represented by (see WO 08/148570),

[B-23.39] Formula (s3)

A compound represented by (see WO 92/012970),

[B-23.40] Formula (s4)

A compound represented by (see WO 12/084812),

[B-23.41] Formula (s5)

A compound represented by (gougerotin),

[B-23.42] Formula (s6)

A compound represented by (ningnanmycin),

[B-23.43] Formula (s7)

A compound represented by (see WO 10/136475),

[B-23.44] Formula (s8)

A compound represented by (see WO 14/010737),

[B-23.45] Formula (s9)

A compound represented by (see WO 11/0805084),

[B-23.46] Formula (s10)

A compound represented by (see WO 11/137002),

[B-23.47] Formula (s11)

A compound represented by (see WO13 / 162072),

[B-23.48] Formula (s12)

A compound represented by (see WO 08/110313),

[B-23.49] Formula (s13)

A compound represented by (see WO09 / 156098),

[B-23.50] Formula (s14)

A compound represented by (see WO 12/025557),

[B-23.51] Formula (s15)

A compound represented by (see WO 14/006945),

[B-23.52] Formula (s16)

[Wherein, A3 represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a cyano group, and A4 represents a hydrogen atom, a C1 to C6 alkyl group, or C1 to C6 It represents a haloalkyl group or a C3 to C8 cycloalkyl group. A compound represented by the formula] (see WO 14/105675),

[B-23.53] Formula (s17)

[Wherein, m1 represents an integer of 0 to 3, A5 and A6 are each independently a halogen atom, or a C1-C6 alkyl group, and A7 and A8 are each independently, A halogen atom or a C1 to C6 alkoxy group is represented, and when m1 is 2 or more, two or more of A7 represent independent substituents and may be the same or different. A compound represented by (see WO09 / 137538, WO09 / 137651),

[B-23.54] Formula (s18)

[Wherein, A9 and A10 are each independently a hydrogen atom or a halogen atom, A11 is a halogen atom, A12 is a halogen atom, or a C1-C6 alkyl group, and A13 is And a halogen atom, a cyano group, a C1-C6 alkyl group, or a C1-C6 alkoxy group. A compound represented by (see WO 12/031061),

[B-23.55] Formula (s19)

[Wherein, m2 represents an integer of 0 to 6, and A14 and A15 are each independently a halogen atom, a cyano group, or a C1-C6 alkyl group, and A16 is a hydrogen atom or a halogen atom Or a C1 to C6 alkoxy group, A17 represents a halogen atom or a C1 to C6 alkoxy group, and when m2 is 2 or more, two or more of A17 each represent an independent substituent, which are the same or It may be different. A compound represented by (see WO05 / 121104),

[B-23.56] Formula (s20)

[Wherein, A18 and A19 are each independently a halogen atom, a cyano group, or a C1-C6 alkyl group, and A20, A21 and A22 are each independently a hydrogen atom, a halogen atom, Or a C1 to C6 alkoxy group. A compound represented by (see WO07 / 066601),

[B-23.57] Formula (s21)

[Wherein, A23 and A24 each independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group, and X represents an oxygen atom or a sulfur atom. A compound represented by (see WO07 / 087906, WO09 / 016220, WO10 / 130767),

[B-23.58] Formula (s22)

[Wherein, m3 represents an integer of 0 to 5, and A25 represents a halogen atom, a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, Or a C3 to C8 cycloalkyl group, and when m3 is 2 or more, two or more A25's each independently represent a substituent and may be the same or different. A compound represented by the formula (see WO 13/092224),

[B-23.59] Formula (s23)

[Wherein, A26 represents a hydrogen atom or a halogen atom, and V1 and V2 are each independently an oxygen atom or a sulfur atom. A compound represented by the formula] (see WO 12/025450),

[B-23.60] Formula (s24) or Formula (s25)

[Wherein, m4 represents an integer of 0 to 5; A27 represents a C1 to C6 alkyl group; A28 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group] And when m4 is 2 or more, two or more of A28 each independently represent a substituent, which may be the same or different, and A29 is a C1-C6 alkyl group, a C2-C6 alkenyl group, or C3 Represents an alkynyl group of -C6. A compound represented by the formula (see WO 13/037717),

[B-23.61] Formula (s26) or Formula (s27)

[Wherein, m5 represents an integer of 0 to 5, A30 represents a C1 to C6 alkyl group, and A31 represents a halogen atom, a cyano group, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group] And when m5 is 2 or more, two or more of A31 each independently represent a substituent, which may be the same or different, and A32 is a C1 to C6 alkyl group, a C2 to C6 alkenyl group, or C3 Represents an alkynyl group of -C6. A compound represented by the formula (see WO 13/037717),

[B-23.62] Formula (s28)

[Wherein, A33, A34, A35, and A36 are each independently a hydrogen atom or a halogen atom, and A37 represents a hydrogen atom, an acetyl group, or a benzoyl group. A compound represented by (see WO06 / 031631 and WO10 / 069882),

[B-23.63] Formula (s29)

[Wherein, A38 represents a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group, and A39 and A40 each independently represent a hydrogen atom or a halogen atom. A compound represented by the formula (see WO 14/043376),

[B-23.64] Formula (s30)

[Wherein, A41 represents a hydrogen atom, a hydroxyl group (-SH), a thiocyanate group (-SCN), or a C1-C6 alkylthio group, and A42, A43, A44 and A45 are each independently , A hydrogen atom, or a halogen atom. A compound represented by the formula] (see WO09 / 077443),

[B-23.65] Formula (s31) or Formula (s32)

[Wherein, A46 represents a hydrogen atom or a halogen atom, A47 represents a C1-C6 alkyl group, and A48 represents a halogen atom. A compound represented by (see WO 11/070771),

[B-23.66] Formula (s33)

[Wherein, A49, A50 and A51 are each independently a hydrogen atom or a halogen atom. And the like (see WO 11/081174) and the like.

Specific components included in the insecticide which can be used in combination with the compound of the present invention are exemplified in the following group c and include salts, isomers and N-oxides thereof. However, known insecticides are not limited to these.

Group c:
c-1: Carbamate-based acetylcholine esterase (AChE) inhibitor [c-1.1] Phosphocarb (phosphocarb), [c-1.2] alanicarb (alycarb), [c -1.3] butocarboxim, [c-1.4] butoxycarboxim, [c-1.5] thiodicarb, [c- 1.6] thiophanox (thiofanox) ), [C-1.7] aldicarb (aldicarb), [c-1.8] bendiocarb, [c-1.9] benfuracarb (benfuracarb), [c-1.10] carbaryl (carbacarb) ryl), [c-1.11] carbofuran, [c-1.12] carbosulfan, [c-1.13] ethiophenecarb, [c-1.14] fenobucarb (c) fenobucarb), [c-1.15] formetanate, [c-1.16] furathiocarb, [c-1.17] isoprocarb, [c-1.18] methiocarb [C-1.19] mesomyl (methhomyl), [c-1. 20] oxamyl, [c-1. 21] pirimicarb (pirimicarb), [c-1. 22] propoxur, c-1.23] trimethacarb, [c-1. 24] XMC (3,5-xylyl methylcarbamate), [c-1. 25] allyxycarb, [c-1. 26] aldoxycarb (Aldoxycarb), [c-1.27] bufencarb, [c-1. 28] butacarb, [c-1. 29] carbanolate, [c-1. 30] metholcarb (metolcarb) ), [C-1.31] xylylcarb, [c-1. 32] phenothiocarb, [c-1. 33] xylylcarb, [c-1. 34] bendaceocarb bendiocarb), and the like.

c-2: Organophosphorus acetylcholine esterase (AChE) inhibitor [c-2.1] acephate, [c-2.2] azamethiphos (azamethiphos) as an organophosphorus acetylcholine esterase (AChE) inhibitor [C-2.3] Azinphos-methyl (azinphos-methyl), [c-2.4] Azinphos-ethyl (azinphos-ethyl), [c-2.5] Ethephon, [c-2.6] ] Cadusafos, [c-2.7] chlorethoxyphos (chlorethoxyfos), [c-2.8] chlorfenvinphos, [c-2.9] chlormephos, [c-] 2.10] Black Lupyrifos (chlorpyrifos), [c-2.11] chlorpyrifos-methyl (chlorpyrifos-methyl), [c-2.12] coumaphos (coumaphos), [c-2.13] cyanophos (cyanophos), [c-2. 14] Demeton-S-methyl (demeton-S-methyl), [c-2.15] diazinon, [c-2.16] diclofenthion, [c-2.17] dichlorvos (dichlorvos) [C-2.18] dicrotophos, [c-2.19] dimethoate, [c-2. 20] dimethylvinphos, [c-2.21] disulfo Ton (disulfoton), [c-2.22] O-ethyl O-4-nitrophenyl phenyl phosphonothioate, [c-2.23] ethion, [c-2 .22] c-2.24] ethoprophos (ethoprophos), [c-2.25] famhur (famphur), [c-2.26] fenamiphos (fenamiphos), [c-2.27] fenitrothion, [c- 2.28] fenthion, [c-2.29] phosthiazate, [c-2.30] heptenophos, heptenophos, [c-2.31] isofenphos-methyl isofenphos-methyl), [c-2.32] isocarbophos (Isocarbophos), [c-2.33] isoxathion, [c-2.34] malathion, [c-2.35] mecarbam (c) mecarbam), [c-2.36] methamidophos (methhamidophos), [c-2.37] methidathion, [c-2.38] mevinphos (mevinphos), [c-2.39] monocrotophos (monocrotophos) ), [C-2.40] naled (naled), [c-2.41] omethoate, [c-2.42] oxydemeton-methyl (oxydemeton-methyl), [c-2.4] Parathions, [c-2.44] parathion-methyl, [c-2.45] phenthoate, [c-2.46] phorate, [c-2] .47] Phosalone (phosalone), [c-2.48] phosmet (phosmet), [c-2.49] phosphamidon, [c-2.50] phoxim, [c-2.51] Pirimiphos-methyl, [c-2.52] profenofos, [c-2.53] propetanphos, [c-2.54] prothiophos, [c-2] .55] Pyraclofos, [c-2.56] pyridaphenthion, [c-2.57] quinalphos, [c-2.58] sulfotep, sulfotep, [c-2.59] tebupilimphos ( tebupirimfos), [c-2.60] temephos (temephos), [c-2.61] terbuphos (terbufos), [c-2.62] thiometon (thiometon), [c-2.63] triazophos (triazophos) [C-2.64] trichlorfon (tricholfon), [c-2.65] vamidothion, [c-2.66] chlorothion, [c-2.67] bromphene Nphoss (bromfenvinfos), [c-2.68] bromophos (bromophos), [c-2.69] bromophos-ethyl (bromophos-ethyl), [c-2.70] butathiophos (butathiofos), [c-2. 71] carbophenothion, [c-2.72] chlorphoxim, [c-2.73] sulprofos, [c-2.74] diamidafos, [c-2. 75] Tetrachlorvinphos (tetrachlorovinphos), [c-2.76] propaphos, [c-2.77] mesulfenphos, [c-2.78] dioxabenzo Dioxabenzofos, [c-2.79] etrimfos, [c-2.80] oxydeprofos, [c-2.81] formothione, [c-2.82] Fensulfothion (fensulfothion), [c-2.83] Isazophos (isazofos), [c-2.84] imicyafos (imicyafos), [c-2.85] Isamidophos (isamidofos), [c-2.86] Thionazine ( Thionazin), [c-2.87] fosthietan, etc. may be mentioned.

c-3: GABAergic Chloride Channel Blocker As a GABAergic Chloride Channel Blocker [c-3.1] chlordane (chlordane), [c-3.2] endosulfan (endosulfan), [c-3.3] Lindane, [c-3.4] dienochlor, [c- 3.5] ethiprole, [c-3.6] fipronil, [c-3.7] aceto There are aproe (acetoprole) and the like.

c-4: Sodium channel modulator [c-4.1] acrinathrin (acrinathrin), [c-4.2] allethrin [(1R) -isomer] (allethrin [(1R) -isomer]), as a sodium channel modulator [C-4.3] bifenthrin, [c-4.4] bioallethrin, [c-4.5] bioallethrin, S-cyclopentenyl isomer, [c- 4.6] bioresmethrin (bioresmethrin), [c-4.7] cycloprothrin, [c-4.8] cyfluthrin, [c-4. Beta-cyfluthrin (beta-cyfluthrin), [c-4. 10] cyhalothrin (cyhalothrin), [c-4. 11] gamma-cyhalothrin (gamma-cyhalothrin), [c-4. 12] lambda-cyhalothrin (lambda) -Cyhalothrin), [c-4.13] cypermethrin (cypermethrin), [c-4. 14] alpha-cypermethrin (alpha-cypermethrin), [c-4. 15] beta-cypermethrin (beta-cypermethrin) [C-4.16] theta-cypermethrin (theta-cypermethrin), [c-4. 17] zeda-cypermethrin (zeta-cypermethrin), [c-4. 18] cifeno Trin [(1R) -trans-isomer] (cyphenothrin [(1R) -trans-isomer]), [c-4.19] deltamethrin (deltamethrin), [c-4.20] enpentrin [(EZ)-(1R )-Isomer] (empenthrin [(EZ)-(1R)-isomer]), [c-4.21] esfenvalerate, [c-4.22] ethofenprox, [c- 4.23] fenpropathrin, [c-4.24] fenvalerate, [c-4. 25] flucythrinate, [c-4. 26] flumethrin (flumethrin) [C-4.27] Tau-fluvalinate (tau-fluvalinate), [c-4. 28] halfenprox (halfenprox), [c-4. 29] imiprothrin (imiprothrin), [c-4. 30] ] Methothrin (methothrin), [c-4.31] methofluthrin (metofluthrin), [c-4. 32] epsilon-methofluthrin (epsilon-metofluthrin), [c-4. 33] monfluorothrin (momfluorothrin), [c] -4.34] epsilon-monfluorothrin (epsilon-momfluorothrin), [c-4.35] permethrin, [c-4.36] phenothrin [(1R) -trans-a] [Somer] (phenothrin [(1R) -trans-isomer]), [c-4.37] prarethrin, [c-4. 38] resmethrin, [c-4. 39] kadethrin [C-4.40] silafluofen (silafluofen), [c-4. 41] tefluthrin (tefluthrin), [c-4. 42] tetramethrin (tetramethrin), [c-4. 43] tetramethrin [(1 R)- Isomers] (tetramethrin [(1R) -isomer]), [c-4.44] tralomethrin, [c-4. 45] transfluthrin, [c-4. 46] ZXI8 901 (3- (4-bromophenoxy) phenyl] -cyanomethyl 4- (difluoromethoxy) -α- (1-methylethyl) benzeneacetate), [c-4.47] biopermethrin (biopermethrin), [c-4.48] framethrin (Furamethrin), [c-4.49] profluthrin (profluthrin), [c-4. 50] flubrocythrinate, [c- 4.51] dimefluthrin, [c- 4.52] DDT (dichloro-diphenyl-trichloroethane), [c-4.53] methoxychloro, [c-4. 4] phenothrin (phenothrin), and the like [c-4.55] fluvalinate (fluvalinate).

c-5: Nicotinic acetylcholine receptor (nAChR) competitive modulator As a nicotinic acetylcholine receptor (nAChR) competitive modulator, [c-5.1] acetamiprid (acetamiprid), [c-5.2] clothianidin (clothianidin) ), [C-5.3] dinotefuran, [c-5.4] imidacloprid (imidacloprid), [c-5.5] nitenpyram (nitenpyram), [c-5.6] thiacloprid, [C-5.7] Thiamethoxam, [c-5.8] Nicotine (nicotine), [c-5.9] Nicotine Sulfate, [c-5. 10] Sul Kisafuroru (sulfoxaflor), [c-5.11] Furupirajifuron (flupyradifurone), and the like [c-5.12] triflupromazine meso pyridinium beam (triflumezopyrim).

c-6: Nicotinic acetylcholine receptor (nAChR) allosteric modulator As a nicotinic acetylcholine receptor (nAChR) allosteric modulator, [c-6.1] spinosad (spinosad), [c-6.2] spinetram (spinetram), etc. Can be mentioned.

c-7: Glutamatergic Chloride Channel (GluCl) Allosteric Modulator As a glutamatergic Chloride Channel (GluCl) allosteric modulator, [c-7.1] Abamectin (abamectin), [c-7.2] emamectin benzoate Salts (emamectin benzoate), [c-7.3] lepimectin (lepimectin), [c-7.4] milbemectin, etc. may be mentioned.

c-8: Juvenile hormone analogues As juvenile hormone analogues, [c-8.1] hydroprene (hydroprene), [c-8.2] quinoprene (kinoprene), [c-8.3] methoprene (methoprene) , [C-8.4] phenoxycarb, [c-8.5] pyriproxyfen, and the like.

c-9: Nonspecific (multisite) inhibitor [c-9.1] methyl bromide, [c-9.2] chlorpicrin as nonspecific (multisite) inhibitor [C-9.3] cryolite, [c-9.4] sulfuryl fluoride, [c-9.5] borax (borax), [c-9.6] borax Acid (boric acid), [c-9.7] octaborate disodium salt (disodium octaborate), [c-9.8] metaborate sodium salt (sodium metabolite) [c-9.9] emetic), [c-9.10] dazomet, [c-9.11] metam (m et al., [c-9.12] carbam sodium salt (metham sodium) and the like.

c-10: Chord Organ TRPV Channel Modulator [c-10.1] pymetrozine, [c-10.2] pyrifluquinazon, etc. may be mentioned as a chord organ TRPV channel modulator.

c-11: Acaride growth inhibitor As acaricide growth inhibitor, [c-11. 1] clofenthezine, [c-1 11. 2] diflovidazine, [c-11. 3] hexethiazox (Hexythiazox), [c-11.4] etoxazole, and the like.

c-12: Mitochondrial ATP synthetase inhibitor [c-12.1] diafenthiuron as a mitochondrial ATP synthetase inhibitor, [c-12. 2] azocyclotin (azocyclotin), [c-12. 3] Cyhexatin (cyhexatin), [c-12. 4] fenbutatin oxide, "c-12.5" propargite, "c-12.6" tetradifon, etc. .

c-13: Oxidative phosphorylation uncoupling agent perturbing a proton gradient [c-13.1] chlorfenapyr (chlorfenapyl), [c-13.2] DNOC as an oxidative phosphorylation uncoupling agent disrupting a proton gradient (Dintro-ortho-cresol), [c-13.3] binapacryl, [c-13.4] sulfluramid, and the like.

c-14: Nicotinic acetylcholine receptor (nAChR) channel blocker [c-14.1] bensultap (bensultap), [c-14.2] cartap hydrochloride (cartap) as a nicotinic acetylcholine receptor (nAChR) channel blocker and [c-14.3] thiocyclam (thiocyclam), [c-14.4] monosultap, and the like.

c-15: Chitin biosynthesis inhibitor type 0
As chitin biosynthesis inhibitor type 0, [c-15. 1] bistrifluron (bistrifluron), [c-15. 2] chlorfluazuron (chlorfluazuron), [c-15. 3] diflubenzuron (diflubenzuron), [C-15.4] flucycloxuron, [c-15.5] flufenoxuron, [c-15.6] hexaflumuron, [c-15.7] Lufenuron, [c-15.8] novarron, [c-15.9] noviflumuron, [c-15. 10] teflubenzuron, [c-15. 11] Rifurumuron (triflumuron), and the like.

c-16: Chitin biosynthesis inhibitor type 1
Examples of chitin biosynthesis inhibitor type 1 include [c-16. 1] buprofezin and the like.

c-17: Fly order insect molting inhibitor [c-17. 1] cyromazine etc. is mentioned as a fly order insect molting inhibitor.

c-18: molting hormone (ecdysone) receptor agonist As molting hormone (ecdysone) receptor agonist, [c-18.1] chromafenozide, [c-18. 2] halofenozide, [c-18 .3] methoxyfenozide, [c-18.4] tebufenozide, etc. may be mentioned.

c-19: Octopamine Receptor Agonist [c-19. 1] amitraz etc. may be mentioned as an octopamine receptor agonist.

c-20: mitochondrial electron transport complex III inhibitor [c-20.1] hydramethylnon (hydramethylnon), [c-20.2] acequinocyl as a mitochondrial electron transport complex III inhibitor [C-20.3] Fluacrypyrim, [c-20.4] bifenazate, etc. may be mentioned.

c-21: Mitochondrial electron transport complex I inhibitor (METI)
[C-21.1] fenazaquin, [c-21.2] fenpyroximate, [c-21.3] pyridaben, as mitochondrial electron transfer complex I inhibitor (METI), [C-21.4] pirimidifene (pylimdifen), [c-21.5] tebufenpyrad (tebufenpyrad), [c-21.6] tolfenpyrad (tolfenpyrad), [c-21.7] rotenone etc. Be

c-22: Voltage-gated sodium channel blocker Examples of voltage-gated sodium channel blockers include [c-22.1] indoxacarb, [c-22.2] metaflumizone, and the like.

c-23: Acetyl-CoA carboxylase inhibitor As an acetyl-CoA carboxylase inhibitor, [c-23. 1] spirodiclofen (spirodiclofen), [c-23. 2] spiromesifen, [c-23.3] ] Spirotetramat (spirotetramat) etc. are mentioned.

c-24: Mitochondrial electron transport complex IV inhibitor As a mitochondrial electron transport complex IV inhibitor, [c-24. 1] aluminum phosphide, [c-24.2] calcium phosphide calcium phosphide, [c-24.3] hydrogen phosphide, [c-24.4] zinc phosphide, [c-24.5] calcium cyanide, [c-24.5] -24.6] sodium cyanide (potassium cyanide), [c-24.7] potassium cyanide (sodium cyanide) and the like.

c-25: Mitochondrial electron transport complex II inhibitor As a mitochondrial electron transport complex II inhibitor, [c-25.1] cyenopyraphen (cyenopyrafen), [c-25.2] cyflumethofen (cyflumetofen), [c -25.3] pyflubumide etc. are mentioned.

c-26: Ryanodine receptor modulator [c-26.1] Chlorantraniliprole (chlororantrilipole) as a ryanodine receptor modulator, [c-26.2] cyantraniliriprole (cyantraniliprole), [c-26. 3) Flubendiamide etc. are mentioned.

c-27: Chord organelle modulator with non-specified target site As a chord organ organ modulator with non-specified target region, [c-27.1] flonicamide and the like can be mentioned.

c-28: Other insecticides As another insecticide, [c-28.1] azadirachtin (azadirachtin), [c-28.2] benzoximate, [c-28.3] phenisobromo (Phenisobromolate), [c-28.4] quinomethionate, [c-28.5] dicofol, [c-28.6] pyridalyl, [c-28.7] bromopropi Rate (bromopropylate), [c-28.8] triazamate, [c-28.9] dicyclanil, [c-28. 10] dinobuton, di [c-28.11] dinocup din ocap), [c-28.12] hydrogen cyanide, [c-28. 13] methyl iodide, [c-28. 14] karanjin, [c-28. 15] Mercury chloride (mercury chloride), [c-28.16] methyl isothiocyanate, [c-28.17] pentachlorophenol, [c-28.18] phosphine (phophine), [c] -28.19] Piperonyl butoxide, [c-28.20] polynactin complex (polynactins), [c-28.21] Sabadilla (sabadilla) [C-28.22] sulcofron salt (sulcofuron-sodium), [c-28.23] tribufos (tribufos), [c-28.24] aldrin, [c-28.25] Amidithione, [c-28.26] amidothioate, [c-28.27] aminocarb, [c-28.28] amitone, [c-28. 29] Aramite, [c-28.30] athidathion, [c-28.31] azotoate, [c-28.32] polysulfide barium, [c- 28.30] 8.33] benclothiaz, [c-28.34] 5- (1,3-benzodioxol-5-yl) -3-hexylcyclohex-2-enone (5- (1,3- (1,3-benzodioxol-5-yl)) benzodioxole-5-yl) -3-hexylcyclohexa-2-enone), [c-28.35] 1,1-bis (4-chlorophenyl) -2-ethoxyethanol (1,1-bis (4-chlorophenyl)-) 2-ethoxyethanol), [c-28.36] butonate, [c-28.37] butopyronoxyl, [c-28. 38] 2- (2-butoxyethoxy) ethyl thiocyanate (2- (c) 2-Butoxyethoxy) ethyl thiocyan ate, [c-28.39] camphechlor, [c-28.40] chlorbenside (chlorbenside), [c-28.41] chlordecone (chlordecone), [c-28.42] chlordimeform (chlordimeform) , [C-28.43] chlorphenethol (chlorfenethol), [c-28.44] chlorfenson (chlorfenson), [c-28.45] fluazuron, [c-28.46] methaldehyde (Metaldehyde), [c-28.47] bialaphos (bialaphos), [c-28.48] levamisole hydrochloride (levasol), [c-28.49] amidoflumet (amidofluto) [C-28.50] pyrafluprole, [c-28.51] pyriprole, [c-28.52] tralopyril, [c-28.53] flupyrazophos [C-28.54] diofenolan, [c-28.55] chlorobenzilate, [c-28.56] flufenzine, [c-28.57] benzomate [C-28.58] flufenerim, [c-28.59] albendazole, alcendazole, [c-28. 60] oxybendazole (oxibendazole) [C-28.61] fenbendazole (fenbendazole), [c-28.62] metam sodium (metam-sodium), [c-28. 63] 1,3-dichloropropene (1,3-dichloropropene ), [C-28.64] flomethoquin (flometoquin), [c-28.65] cyclaniliprol (cycliciliprole), [c-28.66] tetraniriprole (tetraniliprole), [c-28.67] Brofuranilide, [c-28.68] Dichloromezotiaz, [c-28.69] Ethylene dibromide, [c-28. 70] Acrylonitrile acrylonitrile, [c-28.71] bis (2-chloroethyl) ether, [c-28.72] 1-bromo-2-chloroethane [C-28.73] 3-bromo-1-chloroprop-1-ene, [c-28.74] bromocyclen, [c-28. 75] Carbon disulfide, [c-28.76] carbon tetrachloride (tetrachloromethane), [c-28.77] nemadectin, [c-28.78] simiazole (cymiazole) [c- 28.79] Calcium polysulfide (calcium polysulfide), [c-28.80] cytokinin (cytokinin), [c-28.81] 2- (octylthio) ethanol, [c-28.82] potassium oleate (potassium oleate), [c -28.83] sodium oleate, [c-28.84] machine oil, [c-28.85] tar oil, [c-28.86] anabacin (c anabasine), [c-28.87] morantel tartrate, [c-28.88] pyrethrum (pyrethrum), [c-28.89] rapeseed oil, [c- 28.90 ] Soy reticin (soybean lecithin), [c-28.91] starch (starch), [c-28.92] hydroxypropyl starch (hydroxypropyl starch), [c-28.93] fatty acid glyceride (decanoyloctanoylglycerol), [c-28] .94] Propylene glycol fatty acid ester, [c-28.95] diatomite, [c-28.96] afoxolaner, [c-28.97] fluaza Indolysine (fluazaindolizine), [c-28.98] afidopyropene, [c-28.99] Halodiamide (cyhalodiamide), [c-28.100] tioxazafen (tioxazafen), [c-28.101] fluhexafon, [c-28. 102] fluralaner, [c-28. 103] Fluxamethamide (fluxametamide), [c-28.104] tetrachlorantraniliprole, [c-28.105] saloraner, [c-28.106] rotiraner, [c-28] .107] cycloxaprid, [c-28.108] fluensulfone, [c-28.109] TPIC ( tripropyl isocyanurate), [c-28.110] D- (1,3-dichloropropene), [c-28.111] peroxocarbonate, [c-28.112] MB-599 (verbutin), [C-28.113] bis (2,3,3,3-tetrachloropropyl) ether (bis (2,3,3,3-tetrachloropropyl) ether), [c-28.114] DCIP (bis (2 -Chloro-1-methylethyl) ether, [c-28.115] ENT-8184 (N- (2-Ethylhexyl) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide), c-28.1 16] Bayer 22408 (O, O-diethyl O-naphthalimido phosphorothioate), [c-28.117] Bayer 32394 (tris (1-dodecyl-3-methyl-2-phenylbenzimidazolium) hexanoferrate,

[C-28.118] Formula (s34)

A compound represented by (see WO 10/051926),

[C-28.119] Formula (s35)

A compound represented by (see WO 13/115391),

[C-28.120] Formula (s36)

A compound represented by (see WO 12/029672),

[C-28.121] Formula (s37)

A compound represented by (see WO06 / 056108),

[C-28.122] Formula (s38)

A compound represented by (see WO 14/053450, WO 15/144683),

[C-28.123] Formula (s39)

A compound represented by (see WO 14/053450, WO 15/144683),

[C-28.124] Formula (s40)

A compound represented by (see WO 14/053450, WO 15/144683),

[C-28.125] Formula (s41)

[Wherein, m 6 represents an integer of 0 to 2]. A compound represented by the formula (see WO 10/129497),

[C-28.126] Formula (s42)

[Wherein, m7 represents an integer of 0 to 2]. A compound represented by the formula (see WO 11/152320),

[C-28.127] Formula (s43)

[Wherein, m8 represents an integer of 0 to 2]. A compound represented by the formula (refer to JP-A No. 27-160813),

[C-28.128] Formula (s44)

[Wherein, A 52 represents a hydrogen atom or a fluorine atom. A compound represented by (see WO 11/134964, WO 14/005982),

[C-28.129] Formula (s45)

[Wherein, m9 represents an integer of 0 to 2, and A53 represents a fluorine atom or a chlorine atom. A compound represented by the formula (see WO 15/02526),

[C-28.130] Formula (s46)

[Wherein, V 3 represents a nitrogen atom, a carbon atom or C—F, and V 4 and V 5 are each independently a nitrogen atom or a carbon atom. A compound represented by the formula (see WO 11/134964 and WO 14/005982),

[C-28.131] formula (s47)

[Wherein, A54 represents a hydrogen atom, a methyl group, a methoxy group, or an ethoxy group, A55 represents a chlorine atom or a methyl group, and A56 represents a methyl group or an ethyl group. A compound represented by (see WO09 / 049851),

[C-28.132] Formula (s48)

[Wherein, A57 represents a hydrogen atom, a fluorine atom or a chlorine atom, and A58 represents

Represents a partial structure selected from the group consisting of A compound represented by the formula (see WO 11/067272),

[C-28.133] Formula (s49)

[Wherein, A59 represents a hydrogen atom, a fluorine atom or a chlorine atom, and A60 represents

Represents a partial structure selected from the group consisting of A compound represented by the formula (see WO 10/090344),

[C-28.134] Formula (s50)

[Wherein, m10 represents an integer of 0 to 2, and A61 represents a trifluoromethyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and A62 represents a hydrogen atom or A trifluoromethyl group is represented, V6 is a nitrogen atom or a carbon atom, and V7 is an oxygen atom or an N-methyl group. A compound represented by the formula (see WO 14/104407),

[C-28.135] Formula (s51)

[Wherein, A63 represents a hydrogen atom or a fluorine atom, and an amido group is bonded to the 4- or 5-position, and A64 is

Represents a partial structure selected from the group consisting of A compound represented by the formula (see WO 15/038503, WO 16/144351, WO 16/144678),

[C-28.136] Formula (s52)

[Wherein, A65 represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group, A66 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group, and A67 and A68 represent And each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with cyano group, an alkyl group optionally substituted with methoxy group, an alkyl group optionally substituted with ethoxy group, Or a C3-C8 cycloalkyl group,
A69 represents a hydrogen atom, a cyano group, a C1 to C6 haloalkyl group optionally substituted with a cyano group, a C1 to C6 alkyl group, or a C3 to C8 cycloalkyl group. A compound represented by (see WO 12/143317 and WO 16/016369),

[C-28.137] Formula (s53) or Formula (s54)

[Wherein, A70 represents a methyl group, an ethyl group, an isopropyl group, a 2,2,2-trifluoroethyl group, or a phenyl group, and A71 represents

Represents a partial structure selected from the group consisting of

And V8 represents an oxygen atom, a sulfur atom, -CH _2- or -CH ₂ CH _2- . A compound represented by (see WO 14/167084, WO 16/055431),

[C-28.138] Formula (s55)

[Wherein, m11 represents an integer of 0 to 1, A73 represents a chlorine atom, a bromine atom, a methyl group or a trifluoromethyl group, and A74 represents a hydrogen atom, a chlorine atom, a bromine atom, a cyano group, Or A represents a hydrogen atom, a chlorine atom or a bromine atom, A 76 and A 77 each independently represent a C 1 to C 6 alkyl group or a C 3 to C 8 cycloalkyl group, A 78 represents a chlorine atom, a bromine atom, a cyano group, a nitro group, a difluoromethyl group or a trifluoromethyl group. A compound represented by the formula (see WO13 / 024009),

[C-28.139] Formula (s56)

[Wherein, A79, A80, A81 and A82 are each independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C3-C8 And a cycloalkoxy group of A compound represented by the formula (see WO 12/027521),

[C-28.140] formula (s57)

[Wherein, m12 represents an integer of 0 to 2, A83 represents a hydrogen atom or a fluorine atom, and A84 represents

Represents a partial structure selected from the group consisting of A compound represented by (see WO 13/162715),

[C-28.141] asinonapyr (acynonapyr),
[C-28.142] Formula (s59)

[A90 represents a halogen atom, a C1 to C6 alkyl group, or a C1 to C6 haloalkyl group, A91 represents a C1 to C6 haloalkyl group, and A92 and A93 are each independently a hydrogen atom, Represents a C1 to C6 alkyl group, an acetyl group, a propionoyl group, a methanesulfonylethyl group, a methoxycarbonyl group or an ethoxycarbonyl group, and A94 and A95 each independently represent a hydrogen atom or a C1 to C6 alkyl group, Or a C1 to C6 haloalkyl group. And the like (see WO 12/164698) and the like.

The mixing ratio of the compound of the present invention to the pest control agent is not particularly limited as long as the effect is exhibited, but generally, the weight of the compound of the present invention is 0.001 to 1000 It is a ratio of 1000, preferably a ratio of 0.01 to 100.

Hereinafter, the present invention will be described in more detail by way of synthetic examples, reference examples and test examples, but the present invention is not limited thereto.

Synthesis Example 1
Synthesis of 3-chloro-1-ethyl-5- (hydroxy (phenyl) methyl) -6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 7)

Phenylmagnesium chloride in 3.3 ml of a THF solution containing 330 mg of 5-chloro-2- (2,4,6-trifluorophenyl) -1-ethyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde 575 μl of a THF solution (2.0 mol / L) was added dropwise under ice-cooling and stirred for 10 minutes. Saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture and the phases were separated, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 353 mg of white amorphous.

Synthesis Example 2
Synthesis of 3-chloro-1-ethyl-5- (methoxy (phenyl) methyl) -6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 8)

3-Chloro-1-ethyl-5- (hydroxy (phenyl) methyl) -6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one 52.3 mg, methanol 53.9 μl and orthoformate To 2 ml of a nitromethane solution containing 146 μl of trimethyl, 1.2 μl of trifluoromethanesulfonic acid was added under ice-cooling and stirred for 15 minutes. After adding saturated sodium hydrogencarbonate aqueous solution and ethyl acetate to the reaction mixture and liquid-separating, the obtained organic layer was wash | cleaned by the saturated salt solution, and it dried with sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 52.6 mg of white amorphous.

Synthesis Example 3
Synthesis of 3-chloro-1-ethyl-5- (fluoro (phenyl) methyl) -6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 9)

3-chloro-1-ethyl-5- (hydroxy (phenyl) methyl) -6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one in 2 ml of a dichloromethane solution containing 53 mg of (diethylamino) Sulfuric trifluoride 21.2 μl was added under ice-cooling and stirred for 10 minutes. After 1N hydrochloric acid and ethyl acetate were added to the reaction mixture and the phases were separated, the obtained organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 44.4 mg of white amorphous.

Synthesis Example 4
Synthesis of 5-benzyl-3-chloro-1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 10)

A dichloromethane solution containing 58.6 mg of 3-chloro-1-ethyl-5- (hydroxy (phenyl) methyl) -6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one and 119 μl of triethylsilane To 2 ml, 1 ml of trifluoroacetic acid was added and stirred at room temperature for 35 minutes. After adding saturated sodium hydrogencarbonate aqueous solution and ethyl acetate to the reaction mixture and liquid-separating, the obtained organic layer was wash | cleaned by the saturated salt solution, and it dried with sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 49.3 mg of a white solid.

[Reference Example 1]
Synthesis of N-phenyl-1- (2,4,6-trifluorophenyl) propane-1-imine

To 30 ml of a dichloromethane solution containing 3.64 ml of aniline and 7.41 ml of triethylamine, 15 ml of a dichloromethane solution containing 4.37 ml of titanium tetrachloride was dropped at 0 ° C. and stirred for 15 minutes. Then, 10 ml of a dichloromethane solution containing 5 g of 1- (2,4,6-trifluorophenyl) propan-1-one was added at 0 ° C., and the mixture was stirred at room temperature for 3.5 hours. To the resulting reaction mixture was added 1N hydrochloric acid and dichloromethane to separate it. The resulting organic layer was washed with water and dried over sodium sulfate. After evaporation under reduced pressure, 7.08 g of a yellow oil containing the title compound was obtained.

¹ H-NMR (CDCl 3) δ: 7.16-7.11 (2H, m), 6.96-6.92 (1H, m), 6.69-6.67 (2H, m), 6. 52-6.49 (2H, m), 2.73 (2H, q, J = 7.4 Hz), 1.25 (3 H, t, J = 7.4 Hz).

[Reference Example 2]
Synthesis of 5-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one

In 70 ml of 1,4-dioxane containing 7.08 g of N-phenyl-1- (2,4,6-trifluorophenyl) propane-1-imine obtained in Reference Example 1, 3.90 g of aluminum chloride and acrylamide 2 Add .08g and stir at 90 ° C for 5 hours. After cooling to room temperature, 1N hydrochloric acid and ethyl acetate were added to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 3.86 g of white solid.

¹ H-NMR (CDCl 3) δ: 6.76-6.72 (2H, m), 6.58 (1H, s), 2.60-2.57 (2H, m), 2.47-2. 45 (2H, m), 1.61 (3H, s).

[Reference Example 3]
Synthesis of 1-ethyl-5-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one

3.86 g of 5-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one, 5.12 ml of ethyl iodide and 20.85 g of cesium carbonate 40 ml of DMF The mixture was stirred at 60 ° C. for 10 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture to separate it. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained solid was washed with diisopropyl ether. The title compound was obtained as 4.01 g of white solid.

¹ H-NMR (CDCl 3) δ: 6.77-6.72 (2H, m), 3.32 (2H, q, J = 7.1 Hz), 2.59-2 .56 (2H, m) , 2.37-2.35 (2H, m), 0.92 (3H, t, J = 7.1 Hz).

[Reference Example 4]
Synthesis of 1-ethyl-5-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one

1-ethyl-5-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one 4.00 g, 2,3-dichloro-5,6-dicyano- 60 ml of a toluene solution containing 6.75 g of p-benzoquinone was stirred at 120 ° C. for 5 hours. Further, 1.69 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone was added to the reaction mixture, and the mixture was stirred at 120 ° C. for 2 hours. After cooling to room temperature, the resulting reaction mixture was filtered. After evaporating the solvent of the organic layer under reduced pressure, the obtained residue was purified by silica gel column chromatography, and then the solid was washed with diisopropyl ether. The title compound was obtained as 3.50 g of a white solid.

¹ H-NMR (CDCl 3) δ: 7.26 (1 H, d, J = 9.5 Hz), 6.88-6.84 (2 H, m), 6.64 (1 H, d, J = 9. 5 Hz), 3.82 (2 H, q, J = 7.1 Hz), 1.81 (3 H, s), 1. 10 (3 H, t, J = 7.1 Hz).

[Reference Example 5]
Synthesis of 3-chloro-1-ethyl-5-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one

3 ml of a DMF solution containing 97 mg of 1-ethyl-5-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one and 49 mg of N-chlorosuccinimide was stirred at 70 ° C. for 4 hours. Further, 32 mg of N-chlorosuccinimide was added to the reaction mixture, and the mixture was stirred at 70 ° C. for 1 hour. After cooling to room temperature, water and ethyl acetate were added to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 86 mg of a white solid.

¹ H-NMR (CDCl 3) δ: 7.50 (1H, s), 6.89-6.85 (2H, m), 3.87 (2H, q, J = 7.1 Hz), 1.82 (3H, s), 1.13 (3H, t, J = 7.1 Hz).

[Reference Example 6]
Synthesis of 3-chloro-5- (dibromomethyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2-one

3-chloro-1-ethyl-5-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one chlorobenzene solution containing 3.86 g of N-bromosuccinimide 4.78 g And 113.9 mg of azobisisobutyronitrile were added and stirred at 110 ° C. for 1 hour. After cooling to room temperature, water and dichloromethane were added to separate the layers. The obtained organic layer was washed successively with 1% aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 5.40 g of a brown oil.

¹ H-NMR (CDCl 3) δ: 8.13 (1H, s), 6.97-6.93 (2H, m), 5.96 (1H, s), 3.81 (2H, q, J = 7.1 Hz), 1.14 (3 H, t, J = 7.1 Hz).

[Reference Example 7]
Synthesis of 5-chloro-1-ethyl-6-oxo-2- (2,4,6-trifluorophenyl) -1,6-dihydropyridine-3-carbaldehyde

3-chloro-5- (dibromomethyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2-one 47 ml of an aqueous solution containing 5.99 g of silver nitrate in an acetonitrile solution containing 5.40 g Was added and stirred at room temperature for 1 hour. The reaction mixture was filtered through celite and washed with ethyl acetate. The obtained organic layer was washed successively with water, 1N hydrochloric acid and saturated brine, and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the obtained solid was washed with diisopropyl ether. The title compound was obtained as 3.56 g of white solid.

¹ H-NMR (CDCl 3) δ: 9.23 (1H, s), 8.12 (1H, s), 6.97-6.94 (2H, m), 3.94 (2H, q, J = 7.1 Hz), 1.20 (3 H, t, J = 7.1 Hz).

Although the compound synthesize | combined according to the above-mentioned Example in Table 5 is shown, it is not limited to these.

Structure A represents

Structure B represents the following.

Next, their ¹ H-NMR data are shown in Table 6 for the compounds listed in Table 5.

Next, the compounds of the present invention are specifically shown to be effective against plant diseases, but are not limited to these examples.

Test Example A Rice Blast Disease After sowing the seeds of the test plant (rice variety: Kouki), cultivation was carried out until the second leaf was developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plants (2.5 ml / pot). After the drug solution had been dried, the plants were spray-inoculated with a conidia suspension of 1-2 × 10 ⁵ plants / ml of Magnaporthe grisea. After inoculation, the cells were left in a wet room at a temperature of 20-23 ° C. for about 24 hours to promote the onset of disease. The degree of onset of the disease 6 to 10 days after inoculation was investigated to evaluate the effect of the drug solution.

[Experimental Example B] Tomato gray mold scab After sowing the seeds of the test plant (tomato variety: large-sized Fukuju), cultivation was continued until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plants (2.5 ml / pot). After the drug solution had been dried, the plants were spray-inoculated with a 4 to 8 × 10 ⁵ / ml conidia suspension of Botrytis cinerea. After inoculation, it was left in a wet room at a temperature of 20-23 ° C. for about 48 hours to promote the onset of the disease. The incidence of disease 2-3 days after inoculation was investigated to evaluate the effect of the drug solution.

[Experiment Example C] Cabbage black soot disease The seeds of the test plant (cabbage cultivar: four seasons harvest) were sowed, and cultivated until cotyledons were developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plants (2.5 ml / pot). After the drug solution had been dried, the plants were spray-inoculated with a 4 to 8 × 10 ⁵ / ml conidia suspension of cabbage black scab (Alternaria brassicicola). After inoculation, it was left in a wet room at a temperature of 20-23 ° C. for about 48 hours to promote the onset of the disease. The incidence of disease 2-3 days after inoculation was investigated to evaluate the effect of the drug solution.

[Test Example D] Barley powdery mildew The seeds of the test plant (barley cultivar: Akagami power) were sown and cultivated until the first leaves were developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plants (2.5 ml / pot). After the drug solution had dried, the conidia of the barley powdery mildew (Blumeria graminis f. Sp. Hordei) were knocked off and inoculated. The degree of onset 6 to 10 days after inoculation was investigated to evaluate its effect.

[Experiment Example E] Wheat leaf rust disease After sowing the seeds of the test plant (wheat cultivar: Norin 61), cultivation was carried out until the first leaf was developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plants (2.5 ml / pot). After the drug solution had been dried, the plants were spray inoculated with 1 to 2 × 10 ⁵ / ml of a summer spore suspension of wheat rust fungus (Puccinia recondita). After inoculation, the cells were left in a wet room at a temperature of 20-23 ° C. for about 24 hours to promote the onset of disease. The incidence of disease 7 to 10 days after inoculation was investigated to evaluate the effect of the drug solution.

[Test Example F] Tomato plague After seeding the seeds of the test plant (tomato variety: large-sized Fukuju), cultivation was carried out until 3 to 5 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plants (2.5 ml / pot). After the drug solution had been dried, the plants were spray-inoculated with 4-8 × 10 ³ / ml of a zoospore suspension of Phytophthora infestans. After inoculation, it was left in a wet room at a room temperature of 20 ° C. for about 24 hours to promote the onset. The degree of onset of disease 5-10 days after inoculation was investigated to evaluate the effect of the drug solution.

[Test Example G] Grape downy mildew Seeds of test plants (grape varieties: neomascat) were sown and cultivated until 3 or 4 true leaves developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plants (2.5 ml / pot). After the drug solution had been dried, the plants were spray-inoculated with a zoospore suspension of 1-2 × 10 ⁴ plants / ml Plasmoparabiticola. After inoculation, it was left in a wet room at a room temperature of 20 ° C. for about 24 hours to promote the onset. The incidence of disease 7 to 10 days after inoculation was investigated to evaluate the effect of the drug solution.

[Test Example H] Cucumber anthracnose After sowing the seeds of the test plant (cucumber variety: Sagami-hanhaku), cultivation was carried out until one true leaf was developed. In the test, the compound of the present invention was dissolved in a dimethylsulfoxide-methanol mixed solution (volume ratio: 9/1) and diluted with well water to a concentration of 250 ppm to obtain a drug solution. The obtained drug solution was sprayed on the test plants (2.5 ml / pot). After the drug solution had been dried, the plants were spray-inoculated with a 2 to 4 × 10 ⁵ / ml conidia suspension of a cucumber anthracnose fungus (Colletotrichum orbiculare). After inoculation, the cells were left in a wet room at a temperature of 20-23 ° C. for about 24 hours to promote the onset of disease. The degree of onset of the disease 6 to 10 days after inoculation was investigated to evaluate the effect of the drug solution.

Regarding the onset degree of the above-mentioned test example, the onset degree of a disease-free plant was 0, the onset degree of a plant in the non-drug treated area was 3, and the onset degree was evaluated every 0.05. In addition, the control value was calculated according to the following calculation formula from the degree of disease onset.
<Control value>
Control value = 100 {1-(n / 3)}
n = Table 7 summarizes the test results of the degree of onset of disease in each drug treatment area. In the table, H indicates that the control value is greater than 50%, and L indicates that the control value is 50% or less.

Since the pyridone compounds of the present invention are novel compounds and can control plant diseases, they are useful as agricultural chemicals, for example, pesticides for agricultural and horticultural plants, particularly as fungicides for agricultural and horticultural plants.

The disclosure of Japanese Patent Application 2017-180568 (filing date: September 20, 2017) is incorporated herein by reference in its entirety.

All documents, patent applications, and technical standards described herein are as specific and individually as individual documents, patent applications, and technical standards are incorporated by reference. Hereby incorporated by reference.

Claims

Formula (1)

[Wherein, R 1 is
Hydroxyl group,
Cyano group,
A C1 to C6 alkyl group optionally substituted with a substituent A,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent A,
A C2-C6 alkenyl group which may be optionally substituted by a substituent A,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent A,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent A,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent A,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent A,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent A,
A C3-C6 haloalkynyloxy group,
Or RaRbN- (wherein Ra and Rb are each independently a hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 And R.sup.A and R.sup.b, together with the nitrogen atom to which they are attached, represent an aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, homopiperidinyl or azocanyl group. Represent;
R2 is
Hydrogen atom,
Nitro group,
Halogen atom,
A C1 to C6 alkyl group optionally substituted with a substituent A,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent A,
A C2-C6 alkenyl group which may be optionally substituted by a substituent A,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent A,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent A,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent A,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent A,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent A,
A C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO2),
Or RdC (= O) — (wherein, Rd represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent B). Represents
X represents an oxygen atom or a sulfur atom;
Y is
An aryl group which may be optionally substituted 0 to 7 as R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently),
Or a heteroaryl group which may be optionally substituted 0 to 4 with R 3 (provided that R 3 s each having 2 or more substituents are each independently);
R3 is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent C,
A C2-C6 alkenyl group which may be optionally substituted by a substituent C,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent C,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent C,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
RaR b N-(wherein, R a and R b are as defined above),
Rc-L- (wherein Rc and L are as defined above),
Rx1C (= O)-(wherein, Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy A group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above),
Or Rx1C (= O) O— (wherein, Rx1 is as defined above);
Z is
An aryl group which may be optionally substituted 0 to 7 as R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
Or a heterocyclic group which may be optionally substituted 0 to 6 with R 4 (provided that each is independently R 2 in the case of 2 or more substituents R 4);
R4 is
Hydroxyl group,
Cyano group,
Nitro group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent C,
A C2-C6 alkenyl group which may be optionally substituted by a substituent C,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent C,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent C,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
An aryl group which may be optionally substituted by a substituent D,
A heteroaryl group which may be optionally substituted by a substituent D,
An aryloxy group which may be optionally substituted by a substituent D,
A heteroaryloxy group which may be optionally substituted by a substituent D,
An aralkyloxy group which may be optionally substituted by a substituent D,
RaR b N-(wherein, R a and R b are as defined above),
Rc-L- (wherein Rc and L are as defined above),
Rx1C (= O)-(where Rx1 is the same as the above),
Rx1C (= O) O- (wherein, Rx1 is as defined above),
Or Rx2C (= O) N (Rx3)-(wherein, Rx2 is a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cyclo An alkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, or RaRbN- (wherein Ra and Rb are as defined above), and Rx3 is A hydrogen atom, a C1 to C6 alkyl group optionally substituted with a substituent B, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group.
W is
A C1 to C6 alkylene group which may be optionally substituted 0 to 2 with R 5 (wherein each of R 5 s is independently substituted);
R5 is
Hydroxyl group,
Cyano group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C3-C8 cycloalkyl group which may be optionally substituted by a substituent C,
A C2-C6 alkenyl group which may be optionally substituted by a substituent C,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent C,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C3 to C8 cycloalkoxy group which may be optionally substituted by a substituent C,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc and L are as defined above),
Or Rx1C (= O) O— (wherein, Rx1 is as defined above);
And, the substituent A is a hydroxyl group, a cyano group, a C3 to C8 cycloalkyl group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group, a C3 to C8 cycloalkoxy group, RaRbN- (where, Ra And Rb is as defined above) and Rc-L- (wherein Rc and L are as defined above) and at least one selected from the group consisting of
The substituent B is at least one selected from the group consisting of a cyano group, a C1 to C6 alkoxy group, a C1 to C6 haloalkoxy group and a C3 to C8 cycloalkoxy group;
The substituent C is a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN -(Wherein, Ra and Rb are as defined above), Rc-L- (wherein, Rc and L are as defined above), Rx1C (= O)-(wherein, Rx1 At least one selected from the group consisting of the groups having the same meanings as described above) and a 3- to 6-membered ring group containing 1 to 2 oxygen atoms;
Substituent D includes a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1 to C6 alkyl group optionally substituted with substituent B, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, C1 to C6. It is at least one selected from the group consisting of a C6 alkoxy group, a C1 to C6 haloalkoxy group, and a C3 to C8 cycloalkoxy group. Or a salt thereof.
Y is
A phenyl group which may be optionally substituted 0 to 5 as R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently),
A pyridyl group which may be optionally substituted 0 to 4 with R 3 (provided that R 3 s each having 2 or more substituents are independent of each other),
A pyridazinyl group, a pyrimidinyl group or a pyrazinyl group which may be optionally substituted 0 to 3 by R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently),
A triazinyl group which may be optionally substituted 0 to 2 as R 3 (however, in the case of disubstituted R 3, each is independent of each other),
Or a tetrazinyl group which may be optionally substituted by R 3;
Z is
A phenyl group which may be optionally substituted 0 to 5 with R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
A naphthyl group which may be optionally substituted 0 to 7 with R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
A pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group (however, in the case of R4 having two or more substituents, they are each independently.
Thienyl group which may be optionally substituted by 0 to 4 R 4, thiazolyl group, isothiazolyl group, thiadiazolyl group, or thiatriazolyl group (However, in the case of R 4 having two or more substituents, they are each independently.),
A pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, or a pentazolyl group (however, in the case of R4 having two or more substituents, they are each independently independent of each other)
Furyl, oxazolyl, isoxazolyl, oxadiazolyl or oxatriazolyl (which may be independently substituted in the case of R4 having 2 or more substituents) which may be optionally substituted by 0 to 3 R 4;
Indolyl, isoindolyl, indazolyl, benzimidazolyl, or benzotriazolyl groups which may be optionally substituted 0 to 6 by R 4 (however, in the case of R 4 having 2 or more substituents, they are each independently),
Benzofuryl group, isobenzofuryl group, benzoxazolyl group, benzoisoxazolyl group, or benzooxadiazolyl group (however, in the case of R4 having two or more substituents, each of which may be optionally substituted 0 to 5 with R 4 be independent.),
A benzothienyl group, a benzothiazolyl group, a benzoisothiazolyl group, or a benzothiadiazolyl group (however, in the case of R4 having 2 or more substituents, they are each independently independent) which may be optionally substituted 0 to 5 with R 4;
Indolizinyl group which may be optionally substituted 0 to 6 by R 4, imidazopyridyl group, pyrazolo pyridyl group, or triazolo pyridyl group (However, in the case of R 4 having 2 or more substituents, they are each independently.),
A pyrrolopyrimidinyl group which may be optionally substituted by 0 to 4 R 4, imidazopyrimidinyl group, pyrazolopyrimidinyl group, triazolopyrimidinyl group, pyrrolopyrazinyl group, imidazopyrazinyl group, pyrazolopyrazinyl group, or triazolopyrazinyl group Group (but in the case of R 4 with 2 or more substituents, each is independent),
A quinolyl group, an isoquinolyl group, a cinolyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, or a naphthyridinyl group which may be optionally substituted 0 to 6 with R 4 (however, in the case of R4 having 2 or more substituents, they are each independently). ,
Or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms,
The compound according to claim 1 or a salt thereof.
R1 is
A C1 to C6 alkyl group optionally substituted with a substituent A,
C1 to C6 haloalkyl group,
A C2-C6 alkenyl group which may be optionally substituted by a substituent A,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent A,
Or C2 to C6 haloalkynyl group;
R2 is
Hydrogen atom,
Halogen atom,
A C1 to C6 alkyl group optionally substituted with a substituent A,
C1 to C6 haloalkyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent A,
A C1 to C6 haloalkoxy group,
Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO2),
Or RdC (= O) — (wherein, Rd represents a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group which may be optionally substituted with a substituent B). Represents
Y is
A phenyl group which may be optionally substituted 0 to 5 as R 3 (however, in the case of R 3 having 2 or more substituents, they are each independently),
Or a pyridyl group which may be optionally substituted 0 to 4 with R 3 (provided that R 3 s each having 2 or more substituents are independently of each other);
R3 is
Hydroxyl group,
Cyano group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
Or Rx1C (= O) O— (wherein, Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1-C6 Or an alkoxy group of C1 to C6, a haloalkoxy group of C1 to C6, a cycloalkoxy group of C3 to C8, or RaRbN- (wherein Ra and Rb are each independently, and optionally substituted by a hydrogen atom or a substituent B Represents a good C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which it is attached is an aziridinyl group, azetidinyl group, pyrrolidinyl group A group, piperidinyl group, homopiperidinyl group, or those forming an azocanyl group).
Z is
A phenyl group which may be optionally substituted 0 to 5 with R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
A pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group (however, in the case of R4 having two or more substituents, they are each independently.
Thienyl group which may be optionally substituted by 0 to 4 R 4, thiazolyl group, isothiazolyl group, thiadiazolyl group, or thiatriazolyl group (However, in the case of R 4 having two or more substituents, they are each independently.),
A pyrrolyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, or a pentazolyl group which may be optionally substituted 0 to 4 by R 4 (however, in the case of R 4 having two or more substituents, they are each independently).
Or R4 represents a furyl group which may be optionally substituted by 0 to 3, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, or an oxatriazolyl group (provided that they are each independently in the case of R4 having 2 or more substituents). ;
R4 is
Hydroxyl group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C2-C6 alkenyl group which may be optionally substituted by a substituent C,
A C 2 -C 6 haloalkenyl group,
A C2 to C6 alkynyl group which may be optionally substituted by a substituent C,
A C2 to C6 haloalkynyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
Rc-L- (wherein Rc and L are as defined above),
Rx1C (= O)-(where Rx1 is the same as the above),
Or Rx1C (= O) O— (wherein, Rx1 is as defined above);
R5 is
Hydroxyl group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
C1 to C6 haloalkyl group,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C1 to C6 haloalkoxy group,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
A C3-C6 haloalkynyloxy group,
Or Rx1C (= O) O— (wherein, Rx1 is as defined above),
A compound according to claim 2 or a salt thereof.
R1 is
A C1 to C6 alkyl group optionally substituted with a substituent A,
Or a C1 to C6 haloalkyl group;
R2 is
Hydrogen atom,
Halogen atom,
A C1 to C6 alkyl group optionally substituted with a substituent A,
Or a C1-C6 alkoxy group optionally substituted by a substituent A;
Y is
Represents a phenyl group which may be optionally substituted 0 to 5 with R 3 (provided that R 3 is 2 or more, each of which is independently of each other);
R3 is
Hydroxyl group,
Cyano group,
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
A C1 to C6 alkoxy group which may be optionally substituted by a substituent C,
A C2-C6 alkenyloxy group which may be optionally substituted by a substituent C,
A C3-C6 alkynyloxy group which may be optionally substituted by a substituent C,
Or Rx1C (= O) O— (wherein, Rx1 is a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, C1-C6 Or an alkoxy group of C1 to C6, a haloalkoxy group of C1 to C6, a cycloalkoxy group of C3 to C8, or RaRbN- (wherein Ra and Rb are each independently, and optionally substituted by a hydrogen atom or a substituent B Represents a good C1 to C6 alkyl group, a C1 to C6 haloalkyl group, or a C3 to C8 cycloalkyl group, or Ra and Rb together with the nitrogen atom to which it is attached is an aziridinyl group, azetidinyl group, pyrrolidinyl group A group, piperidinyl group, homopiperidinyl group, or those forming an azocanyl group).
Z is
A phenyl group which may be optionally substituted 0 to 5 with R 4 (provided that R 4 has 2 or more substituents, each of which is independently of each other),
A pyrazolyl group, an imidazolyl group, or a triazolyl group which may be optionally substituted 0 to 4 with R 4 (however, in the case of R 4 having 2 or more substituents, they are each independently).
Or an oxazolyl group which may be optionally substituted 0 to 3 with R 4, or an isoxazolyl group (provided that R 4 s each having 2 or more substituents each are independently of each other);
R4 is
Halogen atom,
A C1 to C6 alkyl group which may be optionally substituted by a substituent C,
Or a C1 to C6 alkoxy group optionally substituted by a substituent C;
W is
A methylene group which may be optionally substituted by 0 to 2 as R 5, or an ethylene group (provided that they are each independently in the case of R 5 as di-substituted);
R5 is
Hydroxyl group,
Halogen atom,
Or a C1 to C6 alkoxy group optionally substituted by a substituent C,
A compound according to claim 3 or a salt thereof.
An agricultural and horticultural pest control agent containing the compound according to claim 1 or a salt thereof as an active ingredient.
An agricultural and horticultural fungicide comprising the compound according to claim 1 or a salt thereof as an active ingredient.
A method for controlling plant diseases, which comprises applying the agricultural and horticultural pest control agent according to claim 5 to plants, plant seeds or soil on which plants are grown.
A method for controlling plant diseases, which comprises applying the agricultural and horticultural fungicides according to claim 6 to plants, plant seeds, or soil on which plants are grown.