WO2018190325A1

WO2018190325A1 - Wood preservative containing pyridone compound as active component, and use method thereof

Info

Publication number: WO2018190325A1
Application number: PCT/JP2018/015010
Authority: WO
Inventors: 豪毅梅谷; 英明生島; 良平内藤; 河野　敏之; 章大西田; 聖真川口; 英則大同; あゆみ川瀬
Original assignee: 三井化学アグロ株式会社
Priority date: 2017-04-10
Filing date: 2018-04-10
Publication date: 2018-10-18
Also published as: JPWO2018190325A1; JP7071963B2

Abstract

A compound represented by formula (1), or a salt thereof, is provided that is effective as a wood preservative. In the formula, R1 represents an optionally substituted C1-C6 alkyl group, a C1-C6 haloalkyl group, etc., R2 represents a halogen atom, an optionally substituted C1-C6 alkyl group, an optionally substituted C1-C6 alkoxy group, etc., R3 represents a hydrogen atom, a halogen atom, an optionally substituted C1-C6 alkyl group, etc., n represents an integer 0-5, X represents an oxygen atom or a sulfur atom, Y represents a phenyl group having a substituent in an ortho position, a pyridyl group and the bond that includes the dashed line represents a double bond or a single bond.

Description

Wood preservative containing pyridone compound as active ingredient and method of using the same

The present invention relates to a wood preservative containing a pyridone compound as an active ingredient, a wood preservative, an antiseptic / antifungal agent for wood preservation, and a method of using the same.

Woody material is a useful material used in various fields, but it is a disadvantage that the material is destroyed, decomposed or contaminated by organisms such as wood decaying fungi or wood discoloring fungi, and its strength performance and appearance are reduced. have. Various inorganic and organic antiseptic and antifungal agents have been used to prevent biodegradation caused by such wood-rotting fungi. However, it has been pointed out as a problem that such a drug has a large impact on the human body and a large burden on the environment due to the use of a high concentration, and there is a need for a drug that is more effective, economical, and has a low burden on the environment. ing.

With respect to 1,3,5,6-substituted-2-pyridone compounds, for example, 1,3,5,6-substituted-2-pyridone having an aryl group or heteroaryl group at the 3-position as a GABA alpha-2 / 3 ligand Compounds have been disclosed (see eg WO 98/55480). In addition, 1,3,5,6-substituted-2-pyridone compounds having a carboxyl group at the 3-position have been disclosed as therapeutic agents for bacterial infections (see, for example, European Patent No. 0308020).

International Publication No. 98/55480 EP 0308020 specification

However, WO 98/55480 and European Patent No. 0308020 disclose compounds in which the substituent at the 3-position is completely different from the substituent of the compound according to the present invention and has a different chemical structure. There are only. Moreover, all the uses of the compound described in the said patent document are related with a pharmaceutical, and differ from the technical field to which the wood preservative which concerns on this invention belongs.
An object of the present invention is to provide a novel wood preservative having excellent control activity against wood decaying fungi or wood discoloring fungi, a wood preserving fungicide, and a wood preserving antiseptic / antifungal agent. .

In order to solve the above problems, the present inventors have conducted extensive studies on the 1,3,5,6-substituted-2-pyridone compound group and the 1,5,6-substituted-2-pyridone compound group. With respect to the 6-position in the 2-pyridone skeleton, a compound group in which an aryl group or heteroaryl group having a substituent at the ortho position is introduced exhibits excellent control activity against wood-rotting fungi, wood-discoloring fungi, and the like, It has been found useful as a wood preserving agent, a wood preserving fungicide, and a wood preserving antiseptic and antifungal agent, and has completed the present invention.

That is, the present invention is as follows.
[1]
Formula (1)

[Wherein R1 is a hydroxyl group,
A cyano group,
A C1-C6 alkyl group optionally substituted with substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with the substituent A,
A C2-C6 alkenyl group optionally substituted with the substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with substituent A,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with the substituent A,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with the substituent A,
A C2-C6 alkenyloxy group optionally substituted with the substituent A,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with the substituent A,
A C3-C6 haloalkynyloxy group,
Or R10R11N— (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group);
R2 is a halogen atom,
Hydroxyl group,
A cyano group,
Nitro group,
A C1-C6 alkyl group optionally substituted with the substituent B,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with the substituent B,
A C2-C6 alkenyl group optionally substituted with the substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with substituent B,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with the substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with the substituent B,
A C2-C6 alkenyloxy group optionally substituted with the substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with the substituent B,
A C3-C6 haloalkynyloxy group,
R20C (═O) — (wherein R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, a C1-C6 Represents a haloalkyl group, or a C3-C8 cycloalkyl group, or R21 and R22, together with the nitrogen atom to which they are attached, represents an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group. Represents what is to be formed.)
R20C (═O) O— (wherein R20 has the same meaning as above),
A 3- to 6-membered group containing 1 to 2 oxygen atoms,
R23-L2- (wherein, R23 represents a C1 alkyl group ~ C6 or C1 ~ C6 haloalkyl group,, L2 represents S, SO, or SO _2.),
R21R22N- (wherein R21 and R22 are as defined above),
Or R24C (═O) N (R25) — (wherein R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or R21R22N— (wherein R21 and R22 have the same meanings as described above), and R25 is optionally substituted with a hydrogen atom or substituent B1. Represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, which may be
R3 is a hydrogen atom,
Halogen atoms,
Nitro group,
A C1-C6 alkyl group optionally substituted with substituent C,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with substituent C,
A C1-C6 alkoxy group that may be optionally substituted with a substituent C;
A C1-C6 haloalkoxy group,
A C2-C6 alkenyl group optionally substituted with substituent C,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with substituent C,
A C2-C6 haloalkynyl group,
R30-L3- (wherein R30 has the same meaning as R23 above, and L3 has the same meaning as L2 above),
R31R32N- (wherein R31 and R32 have the same meanings as R21 and R22 above),
Or R33C (═O) — (wherein R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group);
n represents an integer of 0 to 5 (provided that when n is 2 or more, R 2 of 2 or more represents an independent substituent);
X represents an oxygen atom or a sulfur atom;
Y represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group;
In the phenyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 4 appropriately,
In the pyridyl group, the pyrazinyl group, the pyrimidinyl group, the pyridazinyl group, the triazinyl group, or the tetrazinyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently selected from 0 to 3 Replace
In the thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 2 appropriately;
A bond including a broken line part represents a double bond or a single bond,
And the substituent A is
Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, R12R13N- (wherein R12 and R13 are each independently Each represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R12 and R13 together with the nitrogen atom to which they are attached, is an aziridinyl group , An azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group), and R14-L1- (wherein R14 is a C1-C6 alkyl group or a C1-C6 haloalkyl group) represents a group, is selected L1 is, S, SO, or from the group consisting of.) representing the SO _2, At least one selected from;
Substituent B is
Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, C2-C6 alkoxyalkoxy group, R21R22N- R21 and R22 are as defined above), R23-L2- (where R23 and L2 are as defined above), R26R27R28Si— (wherein R26, R27 and R28 are each independently And represents an alkyl group of C1 to C6), R26R27R28Si— (CH ₂ ) s—O— (wherein s represents an integer of 1 to 3, and R26, R27 and R28 are as defined above) ), R20C (═O) — (wherein R20 is as defined above), and a group of 3 to 6 membered ring containing 1 to 2 oxygen atoms. That is at least one selected from the group;
Substituent B1 is
At least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group;
Substituent C is
Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, R31R32N- (wherein R31 and R32 are the same as R21 And R22), and R30-L3- (wherein R30 has the same meaning as R14 and L3 has the same meaning as L1), and at least one selected from the group consisting of Seeds;
Substituent D is
At least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group;
Substituent D1 is
Hydroxyl group, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, and C3-C8 cycloalkoxy group Is at least one selected from the group consisting of Or a salt thereof as an active ingredient,

[2]
R1 is a cyano group,
A C1-C6 alkyl group optionally substituted with substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with the substituent A,
A C2-C6 alkenyl group optionally substituted with the substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with substituent A,
Or R10R11N— (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group);
R2 is a halogen atom,
Hydroxyl group,
A cyano group,
A C1-C6 alkyl group optionally substituted with the substituent B,
A C1-C6 haloalkyl group,
A C1-C6 alkoxy group optionally substituted with the substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with the substituent B,
A C2-C6 alkenyloxy group optionally substituted with the substituent B,
A C3-C6 alkynyloxy group optionally substituted with the substituent B,
R20C (═O) O— (wherein R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group) , C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, C1-C6 Or a cycloalkyl group of C3 to C8, or R21 and R22 together with the nitrogen atom to which they are bonded, an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group ),
Or R23-L2- (wherein, R23 represents an alkyl group or a C1 ~ C6 haloalkyl group, a C1 ~ C6, L2 is S, SO, or an SO _2.) Represents;
R3 is a hydrogen atom,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with substituent C,
A C3-C8 cycloalkyl group optionally substituted with substituent C,
A C1-C6 alkoxy group that may be optionally substituted with a substituent C;
A C2-C6 alkynyl group optionally substituted with substituent C,
Or R30-L3- (wherein R30 has the same meaning as R23 above, and L3 has the same meaning as L2 above);
Y represents a phenyl group or a pyridyl group;
In the phenyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 4 appropriately,
In the pyridyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 3 appropriately.
A wood preservative containing the compound according to [1] or a salt thereof as an active ingredient,

[3]
R1 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group optionally substituted with the substituent A;
R2 represents a halogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, or a C1-C6 alkoxy group optionally substituted with the substituent B;
R3 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent C.
A wood preservative containing the compound according to [2] or a salt thereof as an active ingredient,

[4]
A wood preserving method characterized in that the wood preservative according to [1] is processed into a woody material.
[5]
Use of the compound according to [1] as a wood preservative.

According to the present invention, a novel wood preservative having excellent control activity against wood decaying fungi and wood discoloring fungi, a wood preserving fungicide, a wood preserving antiseptic / antifungal agent, and a method of using them Can be provided.

Hereinafter, embodiments for carrying out the present invention will be described in detail.
It should be noted that each term used in the claims and the specification is defined according to a definition generally used in the technical field unless otherwise specified.
In the present specification, abbreviations used are described below.
DMF: N, N-dimethylformamide, THF: tetrahydrofuran, Me: methyl group, Et: ethyl group, Pr: propyl group, Bu: butyl group, Pentyl: pentyl group, Hexyl: hexyl group, Ac: acetyl group, Ph: Phenyl group, Py: pyridyl group, i: iso, sec: secondary, t: tertiary, c: cyclo, =: double bond, ≡: triple bond. In the table columns, a single “-” means no substitution, and Pr, Bu, Pentyl, and Hexyl means normal when there is no prefix.

The definitions of terms used in the present specification are explained below.
The description Cx-Cy has x to y carbon atoms.
The term “optionally substituted” means substituted or unsubstituted. When this term is used, the number of substituents is 1 when the number of substituents is not specified.
The C1-C6 alkyl group may be linear or branched, and is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, t-butyl, pentyl, isopentyl. Group, 2-methylbutyl group, neopentyl group, 1-ethylpropyl 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 group, 2-ethylbutyl group and the like.

The halogen atom is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.

The C1-C6 haloalkyl group represents a group in which the hydrogen in the C1-C6 alkyl group is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent. Specific examples of the C1-C6 haloalkyl group include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a monochloromethyl group, a monobromomethyl group, a monoiodomethyl group, a chlorodifluoromethyl group, a 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.

The C3-C8 cycloalkyl group includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.

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, only one of E-form and Z-form, or a mixture of E-form and Z-form in an arbitrary ratio, it is particularly limited as long as it is in the range of the designated carbon number. Never happen. Specific examples of C2 to C6 alkenyl groups include vinyl, 1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, and 3-pentenyl. Group, 4-pentenyl group, 3-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 4-methyl-3-pentenyl group, And 3-methyl-2-pentenyl group.

The C2-C6 haloalkenyl group represents a group in which the hydrogen atom in the C2-C6 alkenyl group is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent. Specific examples of the C2-C6 haloalkenyl group include 2-fluorovinyl group, 2,2-difluorovinyl group, 2,2-dichlorovinyl group, 3-fluoroallyl group, 3,3-difluoroallyl group, 3, Examples 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 represents an unsaturated hydrocarbon group having one or more triple bonds and being 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, 1-pentynyl group, 2-pentynyl group, and 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-C6 haloalkynyl group represents a group in which the hydrogen atom in the C2-C6 alkynyl group is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent. Specific examples of the C2-C6 haloalkynyl group include 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, 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- And a trifluoro-4-hexynyl group.

The C1-C6 alkoxy group represents a group in which the C1-C6 alkyl group is bonded via an oxygen atom. Specific examples of the C1-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 Group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3-dimethylbutoxy group, 2,3-dimethylbutoxy group, And 2-ethylbutoxy group.

The C1-C6 haloalkoxy group represents a group in which the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent. Specific examples of the C1-C6 haloalkoxy group include difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, 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-tri 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-C8 cycloalkoxy group represents a group in which the C3-C8 cycloalkyl group is bonded via an oxygen atom. Specific examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group.

The C2-C6 alkenyloxy group is a group in which the C2-C6 alkenyl group is bonded through an oxygen atom. In addition, when there is a geometric isomer, only one of E-form and Z-form, or a mixture of E-form and Z-form in an arbitrary ratio, is not particularly limited as long as it is within the specified carbon number range. Never happen. Specific examples of the C2-C6 alkenyloxy group include vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyloxy group 3-pentenyloxy group, 4-pentenyloxy group, 3-methyl-2-butenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group Group, 4-methyl-3-pentenyloxy group, 3-methyl-2-pentenyloxy group and the like.

The C2-C6 haloalkenyloxy group represents a group in which the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent. Specific examples of the C2-C6 haloalkenyloxy group include 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 2,2-dichlorovinyloxy group, 3-fluoroallyloxy group, 3,3-difluoro. Allyloxy group, 3,3-dichloroallyloxy group, 4,4-difluoro-3-butenyloxy group, 5,5-difluoro-4-pentenyloxy group, 6,6-difluoro-5-hexenyloxy group, etc. It is done.

The C3-C6 alkynyloxy group represents a group in which the C3-C6 alkynyl group is bonded via an oxygen atom among the C2-C6 alkynyl groups. 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 -Dimethyl-2-propynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group, 5-hexynyloxy group and the like.

The C3-C6 haloalkynyloxy group represents a group in which the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted with one or more halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different, and the number of substitutions is not particularly limited as long as it can be present as a substituent. Specific examples of the C3-C6 haloalkynyloxy group include 1,1-difluoro-2-propynyloxy group, 4,4-difluoro-2-butynyloxy group, 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 C2-C6 alkoxyalkoxy group is a group in which the hydrogen atom in the C1-C5 alkoxy group in the C1-C6 alkoxy group is optionally substituted with one or more C1-C5 alkoxy groups Represents. There is no particular limitation as long as the total number of carbon atoms is within the specified carbon number range. Specific examples of C2-C6 alkoxyalkoxy groups include methoxymethoxy, ethoxymethoxy, propyloxymethoxy, isopropyloxymethoxy, methoxyethoxy, ethoxyethoxy, propyloxyethoxy, isopropyloxyethoxy, methoxypropyl Examples thereof include an oxy group, an ethoxypropyloxy group, a propyloxypropyloxy group, and an isopropyloxypropyloxy group.

Specific examples of the 3- to 6-membered ring group containing 1 to 2 oxygen atoms include 1,2-epoxyethanyl group, oxetanyl group, oxolanyl group, oxanyl group, 1,3-dioxolanyl group, 1,3- Examples thereof include a dioxanyl group and a 1,4-dioxanyl group.

The pyridone compound according to the present invention includes a compound represented by the following formula (1) and a salt thereof (hereinafter simply referred to as a compound represented by the formula (1) or the present compound).

Hereinafter, Formula (1) is demonstrated.
R1 in the formula (1) is a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-C8 optionally substituted with a substituent A. A C2-C6 alkenyl group optionally substituted with a substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, C2-C6 Haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, substituent C2-C6 alkenyloxy group optionally substituted with A, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent A, C3-C6 Halo alkynyloxy group, or R10R11N- (wherein, R10, and R11 are each independent represent. A hydrogen atom or an alkyl group C1 ~ C6,) represents a.

Among them, R1 is a cyano group, a C1-C6 alkyl group optionally substituted with the substituent A, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with the substituent A, a substituted group. A C2-C6 alkenyl group optionally substituted with a group A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent A, or R10R11N- (where R10 and R11 is as defined above.)
In particular, a C1-C6 alkyl group or a C1-C6 haloalkyl group which may be optionally substituted with the substituent A is preferable.

The “substituent A” in the formula (1) 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, R12R13N. -(Wherein R12 and R13 are each independently a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R12 and R13 are , Together with the nitrogen atom to which it is attached, represents an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group), and R14-L1- (where R14 is represents a C1 alkyl group ~ C6 or C1 ~ C6 haloalkyl group,, L1 is, S, SO, or SO ₂ Represents 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 R14-L1- (wherein R14 and L1 are as defined above),
In particular, a cyano group or a C1-C6 alkoxy group is preferable.

Preferred specific examples of the substituent A include a hydroxyl group; a cyano group;
As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
A methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group as the C1-C6 alkoxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
As a C3-C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
R12R13N— (wherein R12 and R13 have the same meanings as described above), an amino group, a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
And R14-L1- (wherein R14 and L1 are as defined above), a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group Can be mentioned.

As more preferred specific examples of the substituent A, a hydroxyl group; a cyano group;
A cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group;
A cyclopropyloxy group and a cyclobutoxy group as a C3-C8 cycloalkoxy group;
R12R13N- (wherein R12 and R13 have the same meanings as described above), dimethylamino group, ethylmethylamino group, and diethylamino group;
And R14-L1- (wherein R14 and L1 are as defined above) include a methylthio group, a methanesulfinyl group, and a methanesulfonyl group.

R1 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 the substituent A” in R1 of the formula (1) has the same definition as above, preferably a methyl group, 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. In the case of having the substituent A, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent A.

The “C1-C6 haloalkyl group” in R1 of the formula (1) has the same definition as described above, preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoro group. An ethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, and more preferably a 2-fluoroethyl group, a 2,2-difluoroethyl group, or a 2,2,2- A trifluoroethyl group.

The C3-C8 cycloalkyl group in the “C3-C8 cycloalkyl group optionally substituted with the substituent A” in R1 of the formula (1) has the same definition as above, preferably a cyclopropyl group , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. In the case of having the 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 the substituent A” in R1 of the formula (1) has the same definition as above, preferably a vinyl group, 1- It is a propenyl group or an allyl group, more preferably a vinyl group or an allyl group. In the case of having the substituent A, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent A.

The “C2-C6 haloalkenyl group” in R1 of the formula (1) has the same definition as above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 3-fluoroallyl group, or A 3,3-difluoroallyl group, more preferably a 2-fluorovinyl group or a 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with the substituent A” in R1 of the formula (1) has the same meaning as defined above, preferably a propargyl group, 2- It is a butynyl group or a 3-butynyl group, more preferably a propargyl group. In the case of having the substituent A, the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent A.

The “C2-C6 haloalkynyl group” in R1 of the formula (1) has the same definition as above, and is 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 Or a 4,4,4-trifluoro-2-butynyl group.

The C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with the substituent A” in R1 of the formula (1) has the same definition as above, preferably a methoxy group, an ethoxy group , A propyloxy group, an isopropyloxy group, a butoxy group, or an isobutoxy group, and more preferably a methoxy group or an ethoxy group. In the case of having the substituent A, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent A.

The “C1-C6 haloalkoxy group” in R1 of the formula (1) has the same definition as 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 Or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group in the “C3-C8 cycloalkoxy group optionally substituted with the substituent A” in R1 of the formula (1) has the same definition as described above, preferably cyclopropyloxy Group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group. In the case of having the substituent A, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted with the substituent A.

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

The “C2-C6 haloalkenyloxy group” in R1 of the formula (1) has the same definition as above, preferably 2-fluorovinyloxy group, 2,2-difluorovinyloxy group, 3-fluoro An allyloxy group or a 3,3-difluoroallyloxy group, more preferably a 2-fluorovinyloxy group or a 2,2-difluorovinyloxy group.

The C3-C6 alkynyloxy group of “C3-C6 alkynyloxy group optionally substituted with substituent A” in R1 of formula (1) has the same definition as above, preferably a propargyloxy group , 2-butynyloxy group, or 3-butynyloxy group, and more preferably a propargyloxy group. In the case of having the substituent A, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent A.

The “C3-C6 haloalkynyloxy group” in R1 of the formula (1) has the same definition as described above, and is preferably a 4,4-difluoro-2-butynyloxy group, 4-chloro-4,4- 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 group or 4,4,4-trifluoro-2-butynyloxy group.

The C1-C6 alkyl group of “R10R11N—” in R1 of the formula (1) (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group) Synonymous with definition. “R10R11N—” is preferably an amino group, a dimethylamino group, an ethylmethylamino group, and a diethylamino group, more preferably an amino group and a dimethylamino group.

R2 is a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C6 alkyl group that may be optionally substituted with a substituent B, a C1-C6 haloalkyl group, and a C3-optionally substituted C3- A C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with substituent B, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent B, C2- C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent B, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent B, substituted C2-C6 alkenyloxy group optionally substituted with group B, C2-C6 haloalkenyloxy group, C3-C6 alkynyloxy group optionally substituted with substituent B A C3 to C6 haloalkynyloxy group, R20C (═O) — (wherein R20 is a C1 to C6 alkyl group, a C1 to C6 haloalkyl group, a C3 to C8 cycloalkyl group, a C1 to C6 cycloalkyl group, An alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R21R22N— (wherein R21 and R22 are each independently substituted with a hydrogen atom or a substituent B1). Represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R21 and R22 together with the nitrogen atom to which they are bonded, an aziridinyl group, an azetidinyl group, a pyrrolidinyl group , Represents a piperidinyl group, a homopiperidinyl group, or an azocanyl group.), R 0C (═O) O— (where R20 is as defined above), a 3- to 6-membered ring group containing 1 to 2 oxygen atoms, R23-L2- (where R23 is Represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, L2 represents S, SO, or SO ₂ ), R21R22N— (wherein R21 and R22 are as defined above). Or R24C (═O) N (R25) — (wherein R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group) , A C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R21R22N— (wherein R21 and R22 have the same meanings as described above), and R25 is a hydrogen atom or a substituent B1. Place Which may be C1 ~ C6 alkyl group, a cycloalkyl group of haloalkyl group having C1 ~ C6 or C3 ~ C8,. ).

Among them, R2 is a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group optionally substituted with a substituent B, a C1-C6 haloalkyl group, or a C1-C6 optionally substituted with a substituent B. An alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group optionally substituted with the substituent B, a C2-C6 alkenyloxy group optionally substituted with the substituent B, a substituent B Or an optionally substituted C3-C6 alkynyloxy group, R20C (═O) O— (wherein R20 is as defined above), or R23-L2- (wherein R23 and L2 are , As defined above) is preferred,
In particular, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with the substituent B, or a C1-C6 alkoxy group that may be optionally substituted with the substituent B is preferable.

“Substituent B” in formula (1) 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 To C6 alkoxyalkoxy groups, R21R22N- (wherein R21 and R22 are as defined above), R23-L2- (wherein R23 and L2 are as defined above), R26R27R28Si- ( Here, R26, R27, and R28 are each independently a C1-C6 alkyl group.), R26R27R28Si— (CH ₂ ) s—O— (wherein s is an integer of 1 to 3) R26, R27, and R28 are as defined above, R20C (═O) — (wherein R20 is as defined above for R20), and ~ Represents at least one member selected from the group consisting of groups 3 to 6-membered ring containing two oxygen atoms.

Among them, the substituent B is a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C2-C6 alkoxyalkoxy group, R23-L2- (wherein R23 and L2 are as defined above). ), R26R27R28Si— (wherein R26, R27, and R28 are as defined above), R26R27R28Si— (CH ₂ ) s—O— (wherein s, R26, R27, and R28 are R20C (═O) — (wherein R20 is as defined above), or a 3- to 6-membered ring group containing 1 to 2 oxygen atoms is preferred,
In particular, a cyano group or a C1-C6 alkoxy group is preferable.

Preferred specific examples of the substituent B include a hydroxyl group; a cyano group;
As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
A C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
As a C3-C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
Methoxymethoxy, ethoxymethoxy, methoxyethoxy, ethoxyethoxy, and methoxypropyloxy groups as C2-C6 alkoxyalkoxy groups;
R21R22N— (wherein R21 and R22 have the same meanings as described above), and include amino group, dimethylamino group, ethylmethylamino group, diethylamino group, pyrrolidinyl group, and piperidinyl group;
R23-L2- (wherein R23 and L2 have the same meanings as described above), methylthio group, methanesulfinyl group, methanesulfonyl group, trifluoromethylthio group, trifluoromethanesulfinyl group, and trifluoromethanesulfonyl group;
R26R27R28Si- (wherein R26, R27, and R28 are as defined above), a trimethylsilyl group, and a triethylsilyl group;
R26R27R28Si— (CH ₂ ) s—O— (wherein s, R26, R27, and R28 have the same meanings as described above), 2- (trimethylsilyl) ethoxy group, and 2- (triethylsilyl) ethoxy group ;
R20C (═O) — (wherein R20 has the same meaning as above), acetyl group, propionyl group, difluoroacetyl group, trifluoroacetyl group, cyclopropanecarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 3,3,3-trifluoropropyloxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, pyrrolidinyl A carbonyl group and a piperidinylcarbonyl group;
In addition, examples of the 3- to 6-membered ring group containing 1 to 2 oxygen atoms include an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group, and a 1,3-dioxanyl group.

As more preferred specific examples of the substituent B, a hydroxyl group; a cyano group;
A cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group;
A cyclopropyloxy group and a cyclobutoxy group as a C3-C8 cycloalkoxy group;
A methoxymethoxy group, an ethoxymethoxy group, a methoxyethoxy group, and an ethoxyethoxy group as the C2-C6 alkoxyalkoxy group;
R21R22N— (wherein R21 and R22 have the same meanings as described above), a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
R23-L2- (wherein R23 and L2 are as defined above), a methylthio group, a methanesulfinyl group, and a methanesulfonyl group;
R26R27R28Si- (wherein R26, R27, and R28 are as defined above), a trimethylsilyl group;
2- (trimethylsilyl) ethoxy group as R26R27R28Si— (CH ₂ ) s—O— (wherein s, R26, R27 and R28 are as defined above);
R20C (═O) — (wherein R20 has the same meaning as described above), and includes an acetyl group, a difluoroacetyl group, a trifluoroacetyl group, a methoxycarbonyl group, an ethoxycarbonyl group, an aminocarbonyl group, and a dimethylaminocarbonyl group. , Ethylmethylaminocarbonyl group, and diethylaminocarbonyl group;
Examples of the 3- to 6-membered ring group containing 1 to 2 oxygen atoms include a 1,3-dioxolanyl group and a 1,3-dioxanyl group.

The “substituent B1” in the formula (1) is at least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group. To express. Among these, the substituent B1 is preferably a cyano group or a C1-C6 alkoxy group.

Preferred specific examples of the substituent B1 include a cyano group;
A C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
In addition, examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

As a more preferred specific example of the substituent B1, a cyano group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group;
As the C3-C8 cycloalkoxy group, a cyclopropyloxy group and a cyclobutoxy group can be mentioned.

The halogen atom in R2 of the formula (1) has the same definition as described above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
R2 in the formula (1) includes a hydroxyl group, a cyano group, and a nitro group.

The C1-C6 alkyl group in the “C1-C6 alkyl group optionally substituted with the substituent B” in R2 of the formula (1) has the same definition as above, preferably a methyl group, 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. In the case of having the substituent B, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent B.

The “C1-C6 haloalkyl group” in R2 of the formula (1) has the same definition as above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, 2,2,2 A trifluoroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.

The C3-C8 cycloalkyl group in the “C3-C8 cycloalkyl group optionally substituted with the substituent B” in R2 of the formula (1) is as defined above, and preferably a cyclopropyl group , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. In the case of having the substituent B, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent B.

The C2-C6 alkenyl group of “C2-C6 alkenyl group optionally substituted with substituent B” in R2 of formula (1) has the same definition as above, preferably a vinyl group, 1- A propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, or an allyl group. In the case of having the substituent B, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent B.

The “C2-C6 haloalkenyl group” in R2 of the formula (1) has the same definition as above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group, or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with the substituent B” in R2 of the formula (1) has the same definition as above, preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group. In the case of having the substituent B, the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent B.

The “C2-C6 haloalkynyl group” in R2 of the formula (1) has the same definition as above, preferably 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- A 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.

The C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with the substituent B” in R2 of the formula (1) is as defined above, preferably a methoxy group, an ethoxy group Propyloxy group, isopropyloxy group, butoxy group, isobutoxy group or pentyloxy group, more preferably methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butoxy group or pentyloxy group. In the case of having the substituent B, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted by the substituent B.

The “C1-C6 haloalkoxy group” in R2 of the formula (1) has the same definition as above, and is 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 Or a 2,2,2-trifluoroethoxy group.

The C3-C8 cycloalkoxy group of the “C3-C8 cycloalkoxy group optionally substituted with the substituent B” in R2 of the formula (1) has the same definition as described above, preferably cyclopropyloxy Group, a cyclobutoxy group, a cyclopentyloxy group, or a cyclohexyloxy group, and more preferably a cyclopropyloxy group or a cyclobutoxy group. In the case of having the substituent B, the hydrogen atom in the C3-C8 cycloalkoxy group is optionally substituted by the substituent B.

The C2-C6 alkenyloxy group of the “C2-C6 alkenyloxy group optionally substituted with the substituent B” in R2 of the formula (1) has the same definition as above, preferably a vinyloxy group, A 1-propenyloxy group, an allyloxy group, a 1-butenyloxy group, a 2-butenyloxy group, or a 3-butenyloxy group, and more preferably a vinyloxy group, a 1-propenyloxy group, or an allyloxy group. In the case of having the substituent B, the hydrogen atom in the C2-C6 alkenyloxy group is optionally substituted by the substituent B.

The “C2-C6 haloalkenyloxy group” in R2 of the formula (1) has the same definition as above, and preferably a 2-fluorovinyloxy group, a 2,2-difluorovinyloxy group, a 2,2- A dichlorovinyloxy group, a 3-fluoroallyloxy group, a 3,3-difluoroallyloxy group, or a 3,3-dichloroallyloxy group, more preferably a 2-fluorovinyloxy group or 2,2-difluoro It is a vinyloxy group.

The C3-C6 alkynyloxy group of “C3-C6 alkynyloxy group optionally substituted with substituent B” in R2 of formula (1) is as defined above, preferably a propargyloxy group , 2-butynyloxy group, or 3-butynyloxy group, and more preferably a propargyloxy group. In the case of having the substituent B, the hydrogen atom in the C3-C6 alkynyloxy group is optionally substituted by the substituent B.

The “C3-C6 haloalkynyloxy group” in R2 of the formula (1) has the same definition as above, and is preferably a 4,4-difluoro-2-butynyloxy group, a 4-chloro-4,4-difluoro group. -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- A butynyloxy group or a 4,4,4-trifluoro-2-butynyloxy group.

“R20C (═O) —” in R2 of the formula (1) (wherein R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group) , A C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, or R21R22N— (wherein R21 and R22 are each independently a hydrogen atom or a C1-C6 group optionally substituted with a substituent B1). Represents a C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R21 and R22, together with the nitrogen atom to which they are attached, are aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl Each of which represents a group, a homopiperidinyl group, or an azocanyl group). Righteousness and are synonymous. “R20C (═O) —” is preferably an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, a cyclopropanecarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a 2,2-difluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, cyclopropyloxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylaminocarbonyl group, diethylaminocarbonyl group, pyrrolidinylcarbonyl group, and piperidinylcarbonyl group More preferably, acetyl group, difluoroacetyl group, trifluoroacetyl group, methoxycarbonyl group, ethoxycarbonyl group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethyl group Bruno carbonyl group, and a diethylamino group.

R20 of “R20C (═O) O—” in R2 of the formula (1) has the same meaning as described above. “R20C (═O) O—” is preferably an acetyloxy group, a propionyloxy group, a difluoroacetyloxy group, a trifluoroacetyloxy group, a cyclopropanecarbonyloxy group, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, 2 , 2-difluoroethoxycarbonyloxy group, 2,2,2-trifluoroethoxycarbonyloxy group, cyclopropyloxycarbonyloxy group, aminocarbonyloxy group, dimethylaminocarbonyloxy group, ethylmethylaminocarbonyloxy group, diethylaminocarbonyloxy group Group, pyrrolidinylcarbonyloxy group, and piperidinylcarbonyloxy group, more preferably acetyloxy group, difluoroacetyloxy group, trifluoroacetyloxy group. Shi group, methoxycarbonyloxy group, ethoxycarbonyloxy group, aminocarbonyl group, dimethylaminocarbonyl group, ethylmethylamino carbonyloxy groups, and diethylamino carbonyl group.

The “3- to 6-membered ring group containing 1 to 2 oxygen atoms” in R2 of the formula (1) has the same definition as above, and preferably an oxolanyl group, an oxanyl group, a 1,3-dioxolanyl group Or a 1,3-dioxanyl group, and more preferably a 1,3-dioxolanyl group or a 1,3-dioxanyl group.

“R23-L2-” in R2 of Formula (1) (wherein R23 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L2 represents S, SO, or SO ₂ ). ) Are as defined above. “R23-L2-” is preferably a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, a trifluoromethanesulfonyl group, a (chloromethyl) thio group, or a (chloromethane) sulfinyl group. And (chloromethane) sulfonyl group, more preferably, methylthio group, methanesulfinyl group, methanesulfonyl group, (chloromethyl) thio group, (chloromethane) sulfinyl group, and (chloromethane) sulfonyl group. It is done.

R21 and R22 of “R21R22N-” in R2 of the formula (1) have the same meanings as described above. “R21R22N—” preferably includes an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, and a piperidinyl group, and more preferably a dimethylamino group, an ethylmethylamino group, and a diethylamino group. Is mentioned.

“R24C (═O) N (R25) —” in R2 of the formula (1) (wherein R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group) , C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are as defined above), and R25 represents hydrogen. And each term of C1-C6 alkyl group, C1-C6 haloalkyl group, or C3-C8 cycloalkyl group optionally substituted with substituent B1 is as defined above. . R24 is preferably a hydrogen atom, methyl group, ethyl group, difluoromethyl group, trifluoromethyl group, cyclopropyl group, methoxy group, ethoxy group, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy. Group, cyclopropyloxy group, amino group, dimethylamino group, ethylmethylamino group, diethylamino group, pyrrolidinyl group, and piperidinyl group, and more preferably a hydrogen atom, a methyl group, a difluoromethyl group, a trifluoromethyl group. Methoxy group, ethoxy group, amino group, dimethylamino group, ethylmethylamino group, and diethylamino group. R25 is preferably a hydrogen atom, methyl group, ethyl group, propyl group, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, cyanomethyl group, 2-cyanoethyl group, 2,2-difluoroethyl. Group, 2,2,2-trifluoroethyl group, and cyclopropyl group, more preferably hydrogen atom, methyl group, ethyl group, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, A cyanomethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group can be mentioned.

N in the formula (1) is an integer of 0 to 5. However, when n is 2 or more, two or more R2s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.

R3 in formula (1) may be optionally substituted with a hydrogen atom, a halogen atom, a nitro group, a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, or a substituent C. Good C3-C8 cycloalkyl group, C1-C6 alkoxy group optionally substituted with substituent C, C1-C6 haloalkoxy group, C2-C6 alkenyl group optionally substituted with substituent C C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, C2-C6 haloalkynyl group, R30-L3- (wherein R30 has the same meaning as R23 above) L3 is as defined above for L2, and R31R32N— (wherein R31 and R32 are as defined above for R21 and R22), or R33C (═O) — ( In this, R33 represents represents.) An alkyl group of C1 ~ C6, haloalkyl group of C1 ~ C6, or C3 ~ C8 cycloalkyl group,.

Among them, R3 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group that may be optionally substituted with a substituent C, a C3-C8 cycloalkyl group that may be optionally substituted with a substituent C, or a substituent C as appropriate. An optionally substituted C1-C6 alkoxy group, a C2-C6 alkynyl group optionally substituted with a substituent C, or R30-L3- (wherein R30 and L3 are as defined above). Is preferred,
In particular, a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent C is preferable.

The “substituent C” in formula (1) 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, R31R32N. -(Wherein R31 and R32 are as defined above for R21 and R22), and R30-L3- (wherein R30 is as defined above for R14, and L3 is as defined above for L1). Represents at least one selected from the group consisting of: Among them, the substituent C is preferably a cyano group, a C1-C6 alkoxy group, or R30-L3- (wherein R30 and L3 are as defined above),
In particular, a cyano group or a C1-C6 alkoxy group is preferable.

Preferred specific examples of the substituent C include a hydroxyl group; a cyano group;
As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
A C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and an isobutoxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
As a C3-C8 cycloalkoxy group, a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group;
R31R32N— (wherein R31 and R32 have the same meanings as R21 and R22 above), an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, and a piperidinyl group;
And R30-L3- (wherein R30 has the same meaning as R14, and L3 has the same meaning as L1), a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, Examples thereof include a trifluoromethanesulfinyl group and a trifluoromethanesulfonyl group.

As more preferred specific examples of the substituent C, a hydroxyl group; a cyano group;
A cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group;
A methoxy group and an ethoxy group as the C1-C6 alkoxy group;
A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group;
A cyclopropyloxy group and a cyclobutoxy group as a C3-C8 cycloalkoxy group;
R31R32N— (wherein R31 and R32 have the same meanings as described above), a dimethylamino group, an ethylmethylamino group, and a diethylamino group;
And R30-L3- (wherein R30 and L3 are as defined above) include a methylthio group, a methanesulfinyl group, and a methanesulfonyl group.

R3 in the formula (1) includes a hydrogen atom and a nitro group.
The “halogen atom” in R3 of the formula (1) has the same definition as described above, and is preferably a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

The C1-C6 alkyl group in the “C1-C6 alkyl group optionally substituted with substituent C” in R3 of the formula (1) has the same definition as described above, preferably a methyl group, 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, or a propyl group. In the case of having the substituent C, the hydrogen atom in the C1-C6 alkyl group is optionally substituted by the substituent C.

The “C1-C6 haloalkyl group” in R3 of the formula (1) has the same meaning as defined above, and is preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, 2,2,2 A trifluoroethyl group, a 3,3-difluoropropyl group, or a 3,3,3-trifluoropropyl group, more preferably a difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, or 2,2,2-trifluoroethyl group.

The C3-C8 cycloalkyl group in the “C3-C8 cycloalkyl group optionally substituted with the substituent C” in R3 of the formula (1) has the same definition as above, preferably a cyclopropyl group , A cyclobutyl group, a cyclopentyl group, or a cyclohexyl group, and more preferably a cyclopropyl group or a cyclobutyl group. In the case of having the substituent C, the hydrogen atom in the C3-C8 cycloalkyl group is optionally substituted by the substituent C.

The C1-C6 alkoxy group of the “C1-C6 alkoxy group optionally substituted with the substituent C” in R3 of the formula (1) has the same definition as above, preferably a methoxy group, 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. In the case of having the substituent C, the hydrogen atom in the C1-C6 alkoxy group is optionally substituted with the substituent C.

The “C1-C6 haloalkoxy group” in R3 of the formula (1) has the same definition as 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 Or a 2,2,2-trifluoroethoxy group.

The C2-C6 alkenyl group of “C2-C6 alkenyl group optionally substituted with substituent C” in R3 of formula (1) is as defined above, preferably a vinyl group, 1- A propenyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, or a 3-butenyl group, more preferably a vinyl group, a 1-propenyl group, or an allyl group. In the case of having the substituent C, the hydrogen atom in the C2-C6 alkenyl group is optionally substituted by the substituent C.

The “C2-C6 haloalkenyl group” in R3 of the formula (1) has the same definition as above, preferably a 2-fluorovinyl group, a 2,2-difluorovinyl group, a 2,2-dichlorovinyl group. , 3-fluoroallyl group, 3,3-difluoroallyl group, or 3,3-dichloroallyl group, more preferably 2-fluorovinyl group or 2,2-difluorovinyl group.

The C2-C6 alkynyl group of the “C2-C6 alkynyl group optionally substituted with the substituent C” in R3 of the formula (1) has the same definition as defined above, preferably an ethynyl group, 1- A propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group, or a 3-butynyl group, and more preferably an ethynyl group, a 1-propynyl group, or a propargyl group. In the case of having the substituent C, the hydrogen atom in the C2-C6 alkynyl group is optionally substituted by the substituent C.

The “C2-C6 haloalkynyl group” in R3 of the formula (1) has the same definition as described above, and is 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- A 2-butynyl group, more preferably a 3,3-difluoro-1-propynyl group, or a 3,3,3-trifluoro-1-propynyl group.

In “R30-L3-” in R3 of the formula (1), R30 has the same meaning as R23, and L3 has the same meaning as L2. “R30-L3-” preferably includes a methylthio group, a methanesulfinyl group, a methanesulfonyl group, a trifluoromethylthio group, a trifluoromethanesulfinyl group, and a trifluoromethanesulfonyl group, and more preferably a methylthio group, a methanesulfinyl group. Groups, and methanesulfonyl groups.

“R31R32N—” in R3 of the formula (1) has the same meaning as R21 and R22, and is preferably an amino group, a dimethylamino group, an ethylmethylamino group, a diethylamino group, a pyrrolidinyl group, or A piperidinyl group, more preferably a dimethylamino group, an ethylmethylamino group, or a diethylamino group.

Each of “R33C (═O) —” (wherein R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group) in R3 of the formula (1). Terminology is as defined above. “R33C (═O) —” preferably includes an acetyl group, a propionyl group, a difluoroacetyl group, a trifluoroacetyl group, and a cyclopropanecarbonyl group, and more preferably an acetyl group, a difluoroacetyl group, and a triphenyl group. A fluoroacetyl group is mentioned.

X in the formula (1) represents an oxygen atom or a sulfur atom. Preferred X is an oxygen atom.

Y in Formula (1) represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group.
In the phenyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 4 appropriately.
In the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group, or the tetrazinyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently selected from 0 to 3 Replace.
In the thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0-2.

“Substituent D” in formula (1) is selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group Represents at least one kind.
Among them, the substituent D is preferably a halogen atom or a C1-C6 alkyl group,
In particular, a halogen atom is preferable.

As a preferable specific example of the substituent D,
As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;
A methyl group, an ethyl group, and a propyl group as the C1-C6 alkyl group;
A difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group as the C1-C6 haloalkyl group;
A C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
And C1-C6 haloalkoxy groups include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 3,3-difluoropropyloxy group, and 3, A 3,3-trifluoropropyloxy group may be mentioned.

As a more preferred specific example of the substituent D,
A halogen atom, a fluorine atom, a chlorine atom, and a bromine atom;
A methyl group and an ethyl group as the C1-C6 alkyl group;
A methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group as the C1-C6 alkoxy group;
In addition, examples of the C1-C6 haloalkoxy group include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group.

The “substituent D1” in formula (1) is a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 And at least one selected from the group consisting of C3-C8 cycloalkoxy groups.
Among them, the substituent D1 is preferably a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C6 haloalkyl group,
More preferably, a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group is preferable.

As a preferable specific example of the substituent D1, a hydroxyl group;
As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;
A methyl group, an ethyl group, and a propyl group as the C1-C6 alkyl group;
A difluoromethyl group, a trifluoromethyl group, a 2,2-difluoroethyl group, and a 2,2,2-trifluoroethyl group as the C1-C6 haloalkyl group;
As a C3-C8 cycloalkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group;
A C1-C6 alkoxy group as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, and a t-butoxy group;
C1-C6 haloalkoxy groups include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 3,3-difluoropropyloxy, and 3,3 , 3-trifluoropropyloxy group;
In addition, examples of the C3-C8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutoxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

As a more preferred specific example of the substituent D1, a hydroxyl group;
A halogen atom, a fluorine atom, a chlorine atom, and a bromine atom;
A methyl group and an ethyl group as the C1-C6 alkyl group;
A difluoromethyl group and a trifluoromethyl group as a C1-C6 haloalkyl group;
A cyclopropyl group and a cyclobutyl group as the C3-C8 cycloalkyl group;
A methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group as the C1-C6 alkoxy group;
A difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, and a 2,2,2-trifluoroethoxy group as the C1-C6 haloalkoxy group;
As the C3-C8 cycloalkoxy group, a cyclopropyloxy group and a cyclobutoxy group can be mentioned.

Hereinafter, a specific example of Y in formula (1) will be described in detail.
A) When Y is a phenyl group, Y is represented by the formula (a)

(Wherein D and D1 are as defined above, and ma represents an integer of 0 to 4).

In the formula (a), ma represents an integer of 0 to 4.
When ma in the formula (a) is 2 or more, 2 or more D1s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.
In the present specification, when Y is a phenyl group, the ortho position means the position of the phenyl group having the substituent D as shown in the formula (a).
The phenyl group in which the substituent D is located in the ortho position is a feature of the present invention.

A preferred combination of the formula (a) is a 2-D-6-D1-phenyl group, a 2-D-4-D1-phenyl group, or a 2-D-4-D1-6-D1-phenyl group. Here, for example, “2-D-6-D1-phenyl group” means a disubstituted phenyl group having a substituent D at the 2-position and a substituent D1 at the 6-position, and the following description is also the same.

B) When Y is a pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, or tetrazinyl group, Y is a group represented by the formula (b)

(Wherein D and D1 are as defined above, and mb represents an integer of 0 to 3).

G1, G2, G3 and G4 in the formula (b) are each independently a carbon atom or a nitrogen atom. However, at least one of G1, G2, G3 and G4 is a nitrogen atom. Preferred G1, G2, G3 and G4 are any one of G1, G2, G3 and G4 being a nitrogen atom. That is, it is a pyridyl group.
In the formula (b), mb represents an integer of 0 to 3.
When mb in the formula (b) is 2 or more, 2 or more D1s each represent an independent substituent, may be the same or different, and can be arbitrarily selected.

In the present specification, when Y is a pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, or tetrazinyl group, the ortho position means a 6-membered ring having a substituent D as shown in the formula (b). Means the position of
Specific examples of the partial structure of the formula (b) are shown below.

A pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, or tetrazinyl group in which the substituent D is located in the ortho position is a feature of the present invention.

Preferred combinations of formula (b) are 3-D-2-pyridyl group, 3-D-5-D1-2-pyridyl group, 2-D-3-pyridyl group, 2-D-4-D1-3- Pyridyl group, 2-D-6-D1-3-pyridyl group, 2-D-4-D1-6-D1-3-pyridyl group, 4-D-3-pyridyl group, 4-D-2-D1- 3-pyridyl group, 4-D-6-D1-3-pyridyl group, 4-D-2-D1-6-D1-3-pyridyl group, 3-D-4-pyridyl group, or 3-D-5 -D1-4-pyridyl group.

C) When Y is a thienyl group, thiazolyl group, isothiazolyl group, or thiadiazolyl group, Y is a group represented by the formula (c-1)

Formula (c-2)

Or the formula (c-3)

(Wherein D and D1 are as defined above, and mc represents an integer of 0 to 2).

G5 and G6 in formula (c-1), formula (c-2) and formula (c-3) are each independently a carbon atom or a nitrogen atom.
In the formula (c-1), the formula (c-2) and the formula (c-3), mc represents an integer of 0 to 2.
When mc in formula (c-1), formula (c-2), and formula (c-3) is 2, D1 in 2 represents an independent substituent, and may be the same or different and arbitrarily selected can do.

In the present specification, when Y is a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group, the ortho position is represented by the formula (c-1), the formula (c-2), and the formula (c-3). Means the position of the 5-membered ring having the substituent D.
Specific examples of the partial structure of the formula (c-1) are shown below.

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

Specific examples of the substituent of the partial structure of the formula (c-3) are shown below.

The thienyl group, thiazolyl group, isothiazolyl group, or thiadiazolyl group in which the substituent D is located in the ortho position is a feature of the present invention.

The bond including the broken line in Equation (1) is

This represents the location represented by.
The bond including the broken line part in Formula (1) represents a double bond or a single bond.

When the bond including the broken line in formula (1) is a double bond, formula (1a)

(Wherein R1, R2, R3, X, Y and n are as defined in formula (1)), or a salt thereof.

When the bond including the broken line in Formula (1) is a single bond, Formula (1b)

When R3 in the formula (1b) is a substituent other than hydrogen, only one of the R-form and S-form, or a mixture of the R-form and the S-form in an arbitrary ratio.

The compound represented by formula (1) may have one or two axial asymmetry. In this case, the isomer ratio is a single or an arbitrary mixing ratio, and is not particularly limited.
The compound represented by Formula (1) may contain an asymmetric atom. In this case, the isomer ratio is a single or an arbitrary mixing ratio, and is not particularly limited.
The compound represented by Formula (1) may contain geometric isomers. In this case, the isomer ratio is a single or an arbitrary mixing ratio, and is not particularly limited.

The compound represented by the 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, and metal salts such as sodium, potassium, and calcium, but wood preservatives, wood preservatives, and wood preservatives -There is no particular limitation as long as it can be used as an antifungal agent.

Next, the specific compound of the present invention is represented by a combination of the structural formula shown in Table 1, (R2) n shown in Table 2, and X which is an oxygen atom or a sulfur atom. These compounds are for illustrative purposes, and the present invention is not limited thereto.

Hereinafter, for example, the description “2-F—” in Table 2 means that a fluorine atom is bonded to the 2-position of the phenyl group to which (R2) n is bonded, and “2-F-3” The description “—HO—” means that a fluorine atom is bonded to the 2-position and a hydroxyl group is bonded to the 3-position. The description of “2,3-di-F” means that the 2-position and 3 This means that a fluorine atom is bonded to the position, and other descriptions are the same.

Below, the manufacturing method of the compound represented by Formula (1) is illustrated.
[Production Method A]

In the formula, R4 is a hydrogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group that may be optionally substituted with a substituent A, a C1-C6 haloalkyl group, or a C3-optionally substituted C3- A C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with substituent A, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with substituent A, C2- C6 haloalkynyl group, C1-C6 alkoxy group optionally substituted with substituent A, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group optionally substituted with substituent A, substituted A C2-C6 alkenyloxy group optionally substituted with the group A, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group optionally substituted with the substituent A, Represents a 3-C6 haloalkynyloxy group, or R10R11N- (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group), R5 represents a hydrogen atom, Alternatively, it represents a C1-C6 alkyl group, and n, R2, R3, X and Y are as defined above.

Production method A is a method for obtaining a compound represented by the formula (1b-a) containing the compound of the present invention and a production intermediate of the compound of the present invention, wherein the compound represented by formula (3) and R4NH ₂ are obtained. , A production method comprising reacting in the presence of an acid.

R4NH ₂ used in this reaction can be produced by obtaining or known manner as a commercially available product. R4NH 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.

R4NH ₂ used in this reaction may if 1 equivalent or more relative to the compound represented by formula (3), but are not particularly limited as long as the reaction proceeds to the desired, preferably, 1 Equivalent to 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 are particularly limited as long as the target reaction proceeds. Although not preferred, acetic acid is preferred. Further, when using salts with R4NH ₂ and the acidic compound, the use of acid is not essential.

The amount of the acid used in this reaction may if 1 equivalent or more relative to the R4NH _2, is not limited in particular as long as the reaction proceeds to the desired, preferably, one or more equivalents 200 equivalent or less is there. Moreover, when the acid to be 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, dimethoxy Ether solvents such as ethane, tetrahydrofuran, dioxane, alcohol solvents such as methanol, ethanol, isopropanol, benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ethyl acetate, isopropyl acetate, butyl acetate, etc. Ester solvents, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea systems such as 1,3-dimethyl-2-imidazolidinone solvent Dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more. The solvent is preferably an acidic solvent, more preferably acetic acid.

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

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

As a post-treatment of the reaction, it is possible to perform 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 or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used. Can be used for During the 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 Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.

The reaction mixture containing the compound represented by the formula (1b-a) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

The reaction mixture containing the compound represented by the formula (1b-a) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1b-a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

According to production method A, the compound represented by formula (2), which can be produced when R4 represents a hydrogen atom in the compound represented by formula (1b-a), It can be a useful production intermediate for obtaining the compound represented by 1b).

A specific example of the production intermediate represented by the formula (2) is represented by a combination of the structural formula shown in Table 3, (R2) n shown in Table 2, and X which is an oxygen atom or a sulfur atom. These compounds are for illustrative purposes, and the present invention is not limited thereto.

A method for obtaining the formula (1b) of the present invention using the compound represented by the formula (2) as a production intermediate will be described.

[Production method B]

In the formula, Lv represents a methanesulfonyl group, a trifluoromethanesulfonyl group, a p-toluenesulfonyl group, a leaving group such as a halogen atom, and R1, R2, R3, X, Y, and n are as defined above.

Production method B is a method for obtaining a compound represented by formula (1b), which comprises reacting the production intermediate represented by formula (2) with R1Lv in a solvent in the presence of a base. It is a manufacturing method.

R1Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.

The amount of R1Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2), and is not particularly limited as long as the target reaction proceeds. 1 equivalent or more and 10 equivalents or less.

Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, and sodium hydride, but are particularly limited as long as the intended reaction proceeds. It will never be done.

The amount of the base used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (2), and is not particularly limited as long as the target reaction proceeds. 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, 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 can be used alone or in admixture of two or more.

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to 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 intended reaction proceeds, but is usually 0 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.

As a post-treatment of the reaction, it is possible to perform 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 or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used. During the 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 Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.

The reaction mixture containing the compound represented by the formula (1b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but 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 is not decomposed.
The reaction mixture containing the compound represented by the formula (1b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production Method C]

In the formula, SR represents a sulfurizing agent, and R1, R2, R3, Y, and n are as defined above.

Production method C is a production method for obtaining a compound represented by formula (1b-c) among the compounds represented by formula (1b), wherein the compound represented by formula (1b-b) is sulfurated. It is a manufacturing method including making an agent (SR) react in a solvent.

Examples of the sulfurizing agent used in this 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 equivalent or more with respect to the compound represented by the formula (1b-b), and is not particularly limited as long as the target reaction proceeds. However, it is preferably 1 equivalent or more and 10 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Examples thereof include benzene-based solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or in admixture of two or more.

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1b-b). It is as follows.

As a post-treatment of the reaction, it is possible to perform 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 or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used. Can be used for During the 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 Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield. In this reaction, a liquid separation operation is not essential.

The reaction mixture containing the compound represented by the formula (1b-c) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.

The reaction mixture containing the compound represented by the formula (1b-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1b-c) obtained after the solvent is distilled off can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production Method D]

In the formula, R3a is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C2-C6 alkenyl group optionally substituted with C, C2-C6 haloalkenyl group, C2-C6 alkynyl group optionally substituted with substituent C, or C2-C6 haloalkynyl group , Lv, R1, R2, X, Y, and n are as defined above.

In the production method D, in the compound represented by the formula (1b), R3a is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent C, which may be optionally substituted with a substituent C. C3-C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent C A method for synthesizing a compound represented by the formula (1b-e), which is an alkynyl group or a C2-C6 haloalkynyl group, comprising the step of synthesizing a compound represented by the formula (1b-d) with R3aLv in the presence of a base It is a manufacturing method including making it react in a solvent below.

R3aLv used in this reaction can be obtained as a commercial product or can be produced by a known method.
The amount of R3aLv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1b-d), and is not particularly limited as long as the target reaction proceeds, but is preferably Is 1 equivalent or more and 1.8 equivalent or less.

Bases used in this reaction include metal hydrides such as sodium hydride, organic lithiums such as methyl lithium, butyl lithium, sec-butyl lithium, t-butyl lithium, hexyl lithium, lithium diisopropylamide, hexamethyldisilazane Examples thereof include metal amides such as lithium, sodium hexamethyldisilazane, and potassium hexamethyldisilazane.

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

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1b-d). It is as follows.

The temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually from −80 ° C. to 100 ° C. or the boiling point of the solvent.

As a post-treatment of the reaction, it is possible to perform 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 or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, sodium thiosulfate, sulfurous acid An aqueous solution or a salt solution in which a salt containing sulfur such as sodium is dissolved can be arbitrarily used. During the 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 It is possible to add a solvent that is not compatible with water, such as an ether solvent such as t-butyl ether, a halogen solvent such as dichloromethane, dichloroethane, or chloroform, or a hydrocarbon solvent such as hexane, heptane, cyclohexane, or methylcyclohexane. Is possible. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.

The reaction mixture containing the compound represented by the formula (1b-e) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

The reaction mixture containing the compound represented by the formula (1b-e) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1b-e) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production Method E]

In the formula, Ox represents an oxidizing agent, and R1, R2, R3, X, Y, and n are as defined above.

Production method E is a method for obtaining a compound represented by formula (1a), which comprises reacting a compound represented by formula (1b) with an oxidizing agent (Ox) in a solvent. is there.

Examples of the oxidizing agent used in this reaction include metal oxides such as manganese dioxide, benzoquinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, azobisisobutyronitrile, and benzoyl peroxide. 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 with 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 as long as it is 1 equivalent or more with respect to the compound represented by the formula (1b). Equivalent to 200 equivalents.

The solvent used in this reaction is not particularly limited as long as the intended reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, dichloromethane, dichloroethane, chloroform, And halogen-based solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.

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

As a post-treatment of the reaction, it is possible to remove undissolved metals by filtering. Furthermore, 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 or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used. Can be used for During the 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 Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield. In this reaction, a liquid separation operation is not essential.

The reaction mixture containing the compound represented by the formula (1a) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but 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 is not decomposed.
The reaction mixture containing the compound represented by the formula (1a) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

Hereinafter, a method in which the oxidizing agent is a benzoquinone will be described.
The amount of the oxidizing agent used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1b). Equivalent to 20 equivalents.

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 with respect to the compound represented by the formula (1b), the target reaction proceeds. As long as it does, it will not specifically limit. Preferably, the radical initiator is 0.01 equivalent to 1 equivalent and the halogenating agent is 1 equivalent to 3 equivalent.

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

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

[Production Method F]

In the formula, R3b represents a halogen atom, HalR represents a halogenating agent, and R1, R2, X, Y, and n are as defined above.

Production method F is a production method for obtaining a compound represented by formula (1a-b) in which R3b represents a halogen atom among the compounds represented by formula (1a), which is represented by formula (1a-a). And a halogenating agent (HalR) in a solvent.

As the halogenating agent used in this reaction, selectfluoro (N-fluoro-N′-triethylenediamine bis (tetrafluoroborate)), N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, 1 1,3-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 as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-a). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the target reaction proceeds as long as it is 0.5 equivalent or more, and preferably 1 equivalent or more and 5 equivalents or less.

When the halogenating agent used in this reaction is an iodinating 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 do.
When the halogenating agent used in this reaction is an iodinating agent, the amount of acid used is 0.01 equivalent or more with respect to the compound represented by formula (1a-a), Although it does not restrict | limit especially as long as it advances, Preferably it is 0.1 equivalent or more and 3 equivalent or less.

The solvent used in 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 and trifluoromethanesulfonic acid, diethyl ether , Ether solvents such as diisopropyl ether, methyl-t-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 Ester solvents such as ethyl acetate, isopropyl acetate, butyl acetate, nitrile solvents such as acetonitrile, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide 1,3-dimethyl-2-urea-based solvent-imidazolidinone, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1a-a). It is as follows.

The reaction mixture containing the compound represented by the formula (1a-b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

The reaction mixture containing the compound represented by the formula (1a-b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1a-b) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production method G]

In the formula, R3c is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C A C2-C6 alkenyl group optionally substituted with C2, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group optionally substituted with a substituent C, or a C2-C6 haloalkynyl group, J represents an oxygen atom or a sulfur atom, Q represents a hydrogen atom or a metal, and R1, R2, R3b, X, Y, and n have the same meanings as described above.

In the production method G, in the compound represented by the formula (1a), R3c is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent C, which may be optionally substituted with a substituent C. C3-C8 cycloalkyl group, C2-C6 alkenyl group optionally substituted with substituent C, C2-C6 haloalkenyl group, C2-C6 optionally substituted with substituent C Or a haloalkynyl group of C2 to C6, wherein J is an oxygen atom or a sulfur atom, and is a method of synthesizing a compound represented by the formula (1a-b) A compound obtained by a coupling reaction in which R3c-JQ is reacted in the presence of a transition metal.

In the compound represented by the formula (1a-b), preferred R 3b is a chlorine atom, a bromine atom, or an iodine atom.

R3c-JQ used in this reaction is obtained as a commercial 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 R3c-JQ used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). . 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, such as palladium acetate, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, tris (dibenzylideneacetone) dipalladium, tetrakis ( Palladiums such as triphenylphosphine) palladium and bis (triphenylphosphine) palladium dichloride.

The amount of the transition metal used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (1a-b), but is particularly limited as long as the target reaction proceeds. Never happen.

In order to make this reaction proceed efficiently, triphenylphosphine, 1,1′-bis (diphenylphosphino) ferrocene, 2-dicyclohexylphosphino-2′4′6′-triisopropylbiphenyl, 2-di-t -A phosphine ligand such as butylphosphino-2'4'6'-triisopropylbiphenyl can be added.

The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (1a-b), but is particularly limited as long as the target reaction proceeds. It will never be done.

The base used in this reaction is an inorganic base such as sodium carbonate, potassium carbonate or cesium carbonate, or an organic base such as triethylamine, tributylamine or diisopropylethylamine.

The amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). 1 equivalent or more and 50 equivalents or less.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but R3c-JH (wherein R3c has the same meaning as described above and J is an oxygen atom). An alcohol solvent represented by the formula: Can be mentioned. These solvents can be used alone or in admixture of two or more.

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1a-b). It is as follows.

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

As a post-treatment of the reaction, it is possible to perform 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 or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used. Can be used for During the 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 Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield. Further, it is possible to remove insoluble matters by performing a filtration operation, but this is not essential.

The reaction mixture containing the compound represented by the formula (1a-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1a-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production Method H]

In the formula, R3d is a C1-C6 alkyl group optionally substituted with a substituent C, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group optionally substituted with a substituent C, a substituent C Represents an optionally substituted C2-C6 alkenyl group or C2-C6 haloalkenyl group, R3d-B represents an organic boronic acid, and R1, R2, R3b, X, Y and n are as defined above. It is.

In the production method H, R3d in the compound represented by the formula (1a) is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent C, which may be optionally substituted with a substituent C. A compound represented by the formula (1a-d), which may be a C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent C, or a C2-C6 haloalkenyl group. A method of synthesis comprising obtaining a compound of formula (1a-b) and an organoboronic acid (R3d-B) by a Suzuki-Miyaura coupling in the presence of a transition metal and a base Is the method.

In the formula (1a-b), preferred R 3b is a chlorine atom, a bromine atom, or an iodine atom.

R3d-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 commercial product or produced by a known method.
The amount of R3d-B used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). Preferably, it is 1 equivalent or more and 10 equivalents or less.

The transition metals used in this reaction are palladium, nickel, ruthenium, etc., 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, etc. Palladium is mentioned.

In order to advance this reaction efficiently, phosphine ligands such as triphenylphosphine and tricyclohexylphosphine can be added.
The amount of the phosphine ligand used in this reaction is 0.001 equivalent or more and 1 equivalent or less with respect to the compound represented by the formula (1a-b), but is particularly limited as long as the target reaction proceeds. It will never be done.

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

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an ether such as an aqueous solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, etc. And benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene and dichlorobenzene. These solvents can be used alone or in admixture of two or more.

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

The reaction mixture containing the compound represented by formula (1a-d) obtained after evaporation of the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production Method I]

In the formula, R3e represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C, and R1, R2, R3b, X, Y and n are as defined above. .

In the production method I, in the compound represented by the formula (1a), R3e is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group optionally substituted with a substituent C (1a- A method for synthesizing the compound represented by e), comprising obtaining the compound represented by (1a-b) and the terminal alkyne compound by Sonogashira coupling in the presence of a transition metal and a base. It is a manufacturing method.

The terminal alkyne compound used in this reaction can be obtained as a commercial product or produced by a known method. Trimethylsilylacetylene can also be used as the terminal alkyne compound. In this case, it is necessary to perform desilylation after introducing a trimethylsilylethynyl group into the compound represented by the formula (1a-b). For the desilylation, Journal of the American Chemical Society, Vol. 131, No. 2, pp. 634-643 (2009), Journal of the American Chemical Society. And Journal of Organometallic Chemistry (Vol. 696, No. 25, pages 4039-4045 (2011)), Journal of Organometallic Chemistry (Journal of Organometallic Chemistry). It can carry out with reference to nonpatent literatures, such as.

The amount of the terminal alkyne compound used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). Preferably, it is 1 equivalent or more and 10 equivalents or less.

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

The amount of the transition metal used in this reaction may be 0.001 equivalent or more with respect to the compound represented by the formula (1a-b) for palladium and the like, respectively, and the target reaction proceeds. There is no particular limitation as long as it does. A preferable amount is 0.001 equivalent or more and 1 equivalent or less for both.

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 as long as it is 1 equivalent or more with respect to the compound represented by the formula (1a-b). 1 equivalent or more and 50 equivalents or less. In addition, when the organic base is liquid, it can be used as a solvent.

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

The solvent used in this reaction is not particularly limited as long as the desired reaction proceeds, but ether solvents such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, Benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, ester solvents such as ethyl acetate, isopropyl acetate, 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, carbon tetrachloride, triethylamine, Butylamine, isopropylamine, diethylamine, diisopropylamine, organic amine solvents such as diisopropylethylamine. These solvents can be used alone or in admixture of two or more.

As a post-treatment of the reaction, it is possible to perform 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 or the like is dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate or the like is dissolved, or an arbitrary aqueous solution is used. Can be used for During the 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 Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more of them can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield. Further, it is possible to remove insoluble matters by performing a filtration operation, but this is not essential.

The reaction mixture containing the compound represented by the formula (1a-e) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1a-e) obtained after the solvent is distilled off can be purified with an appropriate solvent by washing, reprecipitation, recrystallization, column chromatography or the like. What is necessary is just to set suitably according to the target purity.

[Production Method J]

In the formula, R2a represents a C1 to C6 alkoxy group, nb represents an integer of 0 to 4 (provided that when nb is 2 or more, each of R2 and 2 represents an independent substituent), R1 , R2, R3, X, Y and the broken line part have the same meanings as described above.

Production method J is a method for synthesizing a compound represented by formula (1-b) having a hydroxyl group among the compounds represented by formula (1), wherein R2a is a C1-C6 alkoxy group ( This is a production method comprising obtaining the compound represented by 1-a) by reacting with an acid.

The acid used for this reaction includes boron halides such as boron trichloride and boron tribromide.

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

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but benzene solvents such as benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, and nitrile solvents such as acetonitrile. And halogen solvents such as dichloromethane, dichloroethane, chloroform and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane and methylcyclohexane. These solvents can be used alone or in admixture of two or more.

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1-a). It is as follows.

The reaction mixture containing the compound represented by the formula (1-b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

The reaction mixture containing the compound represented by the formula (1-b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1-b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production Method K]

In the formula, R2b—O— is a C1-C6 alkoxy group optionally substituted with the substituent B, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy optionally substituted with the substituent B. Group, C2 to C6 alkenyloxy group optionally substituted with substituent B, C2 to C6 haloalkenyloxy group, C3 to C6 alkynyloxy group optionally substituted with substituent B, C3 to C6 A haloalkynyloxy group or an R20C (═O) O— group, and Lv, R1, R2, R3, R20, X, Y, nb and the broken line are as defined above.

In the production method K, in the compound represented by the formula (1), R2b—O— may be optionally substituted with a substituent B, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a substituent C3-C8 cycloalkoxy group optionally substituted with B, C2-C6 alkenyloxy group optionally substituted with substituent B, C2-C6 haloalkenyloxy group, optionally substituted with substituent B A C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, or an R20C (═O) O— group (wherein R20 is as defined above). A process for synthesizing a compound represented by formula (1-b) comprising reacting a compound represented by formula (1-b) with R2b-Lv in a solvent in the presence of a base.

R2b-Lv used in this reaction can be obtained as a commercial product or can be produced by a known method.
R2b-Lv used in this reaction may be 1 equivalent or more with respect to the compound represented by formula (1-b), and is not particularly limited as long as the target reaction proceeds, but preferably Is 1 equivalent or more and 10 equivalents or less.

Bases used in this reaction include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, sodium hydride, and organic bases such as triethylamine, tributylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, collidine, and lutidine. However, there is no particular limitation as long as the target reaction proceeds.

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

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1-b). It is as follows.

The temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually −20 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.

The reaction mixture containing the compound represented by the formula (1-c) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.

The reaction mixture containing the compound represented by the formula (1-c) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1-c) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production method L]

In the formula, R2c represents a halogen atom, and R2d is a C1-C6 alkyl group optionally substituted with the substituent B, a C1-C6 haloalkyl group, a C3-C8 optionally substituted with the substituent B A cycloalkyl group, a C2-C6 alkenyl group optionally substituted with a substituent B, or a C2-C6 haloalkenyl group, R2d-B represents an organic boronic acid, R1, R2, R3, nb, X, Y, and the broken line are as defined above.

In the production method L, among the compounds represented by the formula (1), R2d is optionally substituted with a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a substituent B which may be optionally substituted with a substituent B. Of the compound represented by the formula (1-e), which may be a C3-C8 cycloalkyl group, a C2-C6 alkenyl group optionally substituted with the substituent B, or a C2-C6 haloalkenyl group. A synthesis method comprising obtaining by a Suzuki-Miyaura coupling in which a compound represented by the formula (1-d) and an organic boronic acid (R2d-B) are reacted.

In the formula (1-d), R2c is preferably a chlorine atom, a bromine atom, or an iodine atom.

By using the compound represented by formula (1a-b) and R3d-B in production method H instead of the compound represented by formula (1-d) and R2d-B, respectively, production method H The production method L can be carried out according to the above.

[Production method M]

In the formula, R2e represents a C2-C6 alkynyl group or a C2-C6 haloalkynyl group which may be optionally substituted with the substituent B, and R1, R2, R2c, R3, nb, X, Y and the broken line part It is synonymous with the above.

In the production method M, among the compounds represented by the formula (1), R2e is a C2-C6 alkynyl group or a C2-C6 haloalkynyl group which may be optionally substituted with a substituent B (1- A method for synthesizing the compound represented by f), which comprises obtaining the compound represented by the formula (1-d) by Sonogashira coupling with a terminal alkyne compound.

In the compound represented by the formula (1-d), preferable R2c is a chlorine atom, a bromine atom, or an iodine atom.

By using the compound represented by the formula (1a-b) in the production method I instead of the compound represented by the formula (1-d), the production method M can be carried out according to the production method I. .

[Production Method N]

In the formula, Da represents a halogen atom, D1a represents a halogen atom, D1b represents a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or a C3-C8 cycloalkoxy group, and E represents a halogen atom. Represents a carbon atom or a nitrogen atom, and R 1, R 2, R 3, n, X, Q, and a broken line part are as defined above.

In the production method N, among the compounds represented by the formula (1), D1b is a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, or a C3-C8 cycloalkoxy group, and E is a halogen atom. A method for synthesizing a compound represented by formula (1-h), which is a substituted carbon atom or nitrogen atom, comprising reacting a compound represented by formula (1-g) with D1b-Q in a solvent. Manufacturing method.

D1b-Q used in this reaction can be obtained as a commercial 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 D1b-Q used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1-g). Preferably, it is 1 equivalent or more and 30 equivalent or less. Moreover, when Q represents a hydrogen atom, it can be used as a solvent.

The base used in this reaction is preferably an inorganic base such as sodium carbonate, potassium carbonate, cesium carbonate or sodium hydride. Further, when Q is an alkali metal, the use of a base is not essential.

The amount of the base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1-g). 1 equivalent or more and 30 equivalent or less.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but alcohol solvents represented by D1b-H, diethyl ether, diisopropyl ether, methyl-t-butyl ether, dimethoxy Ether solvents such as ethane, tetrahydrofuran and dioxane, 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, carbon tetrachloride etc Halogenated solvents, dimethylsulfoxide, sulfur-based solvents such as sulfolane, acetone, methyl ethyl ketone, ketone solvents such as methyl isobutyl ketone. These solvents can be used alone or in admixture of two or more.

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to the compound represented by the formula (1-g). It is as follows.

The reaction mixture containing the compound represented by the formula (1-h) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but it is not essential.

The reaction mixture containing the compound represented by the formula (1-h) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1-h) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production method O]

In the formula, R2e represents a C1-C6 alkoxy group that may be optionally substituted with the substituent B, R2f represents a C1-C6 alkoxy group that may be optionally substituted with the substituent B, and R2g represents a halogen atom. In the formula, HalR, R1, R3, X, Y and the broken line part are as defined above.

In the production method O, among the compounds represented by the formula (1), R2e is a C1-C6 alkoxy group which may be appropriately substituted with the substituent B, and R2f may be appropriately substituted with the substituent B. A production method for obtaining a compound represented by the formula (1-j), which is a C1-C6 alkoxy group and R2g is a halogen atom, comprising a compound represented by the formula (1-i) and a halogenating agent ( HalR) in a solvent.

The amount of the halogenating agent used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (1-i). Preferably, it is 1 equivalent or more and 10 equivalents or less. However, the amount of the halogenating agent containing hydantoin is not particularly limited as long as the target reaction proceeds as long as it is 0.5 equivalent or more, and preferably 1 equivalent or more and 5 equivalents or less.

When the halogenating agent used in this reaction is an iodinating 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 do.
When the halogenating agent used in this reaction is an iodinating agent, the amount of acid used is 0.01 equivalent or more with respect to the compound represented by formula (1-i), and the target reaction Although it does not restrict | limit especially as long as it advances, Preferably it is 0.1 equivalent or more and 3 equivalent or less.

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but usually 3 to 200 times by weight with respect to the compound represented by the formula (1-i). It is as follows.

The reaction mixture containing the compound represented by the formula (1-j) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

The reaction mixture containing the compound represented by the formula (1-j) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (1-j) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production method P]

In the formula, La represents S, Lb represents SO or SO ₂ , and Ox ′ represents an oxidizing agent.

Production method P during the compound represented by formula (1), a process for the preparation of a compound represented by R1, Lb contained in R2 and R3 is SO or SO ₂ wherein (Lb), the formula ( In 1), it is a production method comprising reacting a compound represented by the formula (La) in which La contained in R1, R2 or R3 is S with an oxidizing agent (Ox ′) in a solvent.

Examples of the oxidizing agent used in this reaction include peroxides such as hydrogen peroxide and meta-chloroperbenzoic acid. In addition, transition metals such as sodium tungstate can be added.

The amount of the oxidizing agent used in this reaction is usually 1.0 equivalent or more and 1.2 equivalent or less with respect to the compound represented by the formula (La) when producing SO, and produces SO ₂ . When doing, it is usually 2 equivalents or more and 10 equivalents or less. Moreover, when adding transition metals, it is 0.001 equivalent or more and 1 equivalent or less normally.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an aqueous solvent, an acidic solvent such as acetic acid, benzene, toluene, xylene, mesitylene, chlorobenzene, dichlorobenzene, etc. Examples thereof include benzene solvents, nitrile solvents such as acetonitrile, and halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride. These solvents can be used alone or in admixture of two or more.

The amount of the solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 times the weight of the compound represented by the formula (1) having the formula (La). More than 200 weight times.

The temperature at which this reaction is carried out is not particularly limited as long as the intended reaction proceeds, but is usually −10 ° C. or higher and 120 ° C. or lower or the boiling point of the solvent or lower.

The reaction mixture containing the compound represented by the formula (Lb) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

The reaction mixture containing the compound represented by the formula (Lb) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (Lb) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

Next, a method for synthesizing the compound represented by Formula (3) described in Production Method A will be described.
[Production method Q]

In the formula, R2, R3, R5, n, X and Y have the same meanings as described above.

Production method Q is a production method of a production intermediate represented by formula (3), in which a compound represented by formula (4) and a compound represented by formula (5) are mixed in a solvent in the presence of a base. It is a manufacturing method including making it react with.

The compound represented by the formula (4) used in this reaction is, for example, Green Chemistry, Vol. 41, pages 580-585, The Journal of Organic Chemistry, No. 65, No. 20, pages 6458-6461 (2000). Etc. can be synthesized by reference.

The compound represented by Formula (5) used for this reaction can be obtained as a commercial product or can be produced by a known method.
The amount of the compound represented by the formula (5) used in this reaction is particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by the formula (4). However, it is preferably 1 equivalent or more and 3 equivalents or less.

The base used in this reaction can be carried out in a catalytic amount, and is not particularly limited as long as the target reaction proceeds, but preferably the compound represented by formula (4) is used. On the other hand, it is 0.01 equivalent or more and 3 equivalent or less.

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

The amount of solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but it is usually 3 to 200 times by weight with respect to 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 intended reaction proceeds, but is usually −50 ° C. or higher and 150 ° C. or lower or the boiling point of the solvent or lower.

The reaction mixture containing the compound represented by the formula (3) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

The reaction mixture containing the compound represented by the formula (3) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by the formula (3) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography or the like with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

[Production method R]

In the formula, R5a represents a C1 to C6 alkyl group, and R2, R3, n, X, and Y are as defined above.

Production method R is a production method of a production intermediate represented by formula (3b) among the compounds represented by formula (3), wherein the compound represented by formula (3a) is subjected to acidic conditions or a base. It is a manufacturing method including making it react in a solvent on 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. Preferably, the amount of the acid is 0. 0 with respect to the compound represented by the formula (3a). 01 equivalents or more. Further, liquid acids can be used as solvents.

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but 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 and 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, etc. No A solvent, dichloromethane, dichloroethane, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.

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

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

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 are not particularly limited as long as the target reaction proceeds.

The base used in this reaction is not particularly limited as long as the target reaction proceeds as long as it is 1 equivalent or more with respect to the compound represented by formula (3a), but preferably 1 equivalent or more. 30 equivalents or less,

The solvent used in this reaction is not particularly limited as long as the target reaction proceeds, but an ether such as an aqueous solvent, diethyl ether, diisopropyl ether, methyl-t-butyl ether, 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 Solvents, amide solvents such as N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, urea solvents such as 1,3-dimethyl-2-imidazolidinone, dichloromethane, dichloroethane Down, chloroform, and halogen solvents such as carbon tetrachloride. These solvents can be used alone or in admixture of two or more.

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

As for the post-treatment of the reaction, the reaction under acidic conditions and the reaction under basic conditions can be performed by a common method. 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, etc. are dissolved, an alkaline aqueous solution in which potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, etc. are dissolved, saline, etc. are optional. Can be used for During the 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 Solvents that are not compatible with water, such as ether solvents such as t-butyl ether, halogen solvents such as dichloromethane, dichloroethane, chloroform, and carbon tetrachloride, and hydrocarbon solvents such as hexane, heptane, cyclohexane, and methylcyclohexane. It is possible to add. Moreover, these solvents can be used alone, or two or more kinds can be mixed in an arbitrary ratio. The number of times of liquid separation is not particularly limited, and can be carried out according to the target purity and yield.

The reaction mixture containing the compound represented by the formula (3b) obtained above can remove moisture with a desiccant such as sodium sulfate or magnesium sulfate, but is not essential.

The reaction mixture containing the compound represented by the formula (3b) obtained above can be distilled off under reduced pressure as long as the compound is not decomposed.
The reaction mixture containing the compound represented by formula (3b) obtained after distilling off the solvent can be purified by washing, reprecipitation, recrystallization, column chromatography, etc. with an appropriate solvent. What is necessary is just to set suitably according to the target purity.

The compound represented by the formula (3b) is represented by the formula (3b ′)

(Wherein R2, R3, n, X and Y are as defined above.)

Is also included. The compound represented by the formula (3b ′) can be handled in the same manner as the compound represented by the formula (3b), and the production method A can be applied. Further, the compound represented by the formula (3b ′) contains an asymmetric carbon, but the isomer mixing ratio may be single or a mixture of any ratio. Further, it may be a mixture of the compound represented by the formula (3b) and the compound represented by the formula (3b ′), and the isomer mixing ratio may be a single compound or a mixture of any ratio.

The compound represented by the formula (1) can be produced by arbitrarily combining the production methods A to R shown above. Alternatively, the compound represented by the formula (1) can also be produced by arbitrarily combining known methods and production methods A to R.

The compound of the present invention can be used for various wood materials in order to prevent decay and discoloration of the wood materials. The term “decay” as used in the present invention means that wood components such as cellulose and lignin are decomposed by wood decay fungi, the structure of the wood collapses and disappears, and material deterioration such as strength reduction and softening is caused. In addition, the color change referred to in the present invention means that the wood material is discolored and contaminated by the wood color changing bacteria, and the appearance of the material is deteriorated.

The compound of the present invention is effective against various wood decay fungi. Wood decay fungi include, for example, Coniophora puteana (Coniophora puteana), Rangetes betulina (Lenzytes betulina), Trametes versientia pula, Lametes verstiola posicola, (Poria vaporaria), Poria viranti (Mawatagsarekin) (Poria vaillanti), Gloeophyllium sepialium (Gloeophyllium sepialium), Glooeophyllium agroatum (Gloeophyllium abietinum), Gloeophyllium trabeum (Grillophyllium trabeum), Gloeophyllium protactum (Kiamitake) Gloeophyllium proteactum, Lentina repiedius lenti・ Lentinus cyathiformes, Lentinas squarolosus (Kenagatake) (Lentinus squarolosus), Schizophyllum commune (Schizophyllum commune), Pakilas panouides Ginkgo biloba (Paxilus panuoides), Homotopsis pulse tris (Ozuratake) (Fomitopis a pastris), Homitopsis relanogi Gilva (Fomitopissis lilacino-gilva), Pleurotus ostrichus Serpula lacrimans (Serpula lacrymans), Serpuura himantoides (Serpula himantoides), Grenospora graphii, Perenoporica Perniporia tephropora), Antrodia xantha, Antrodia bailanti, Pynoporus cocineus, Pycnoporuscocrum Ketomium globussum (Chaetomium globsum), Ketomium alba arenarum (Chaetmium alba-arenulum), Petriella settifera (Trichuras spirialis) umicola grisera), and the like.

The compound of the present invention is also effective against various wood discoloring bacteria. Examples of wood-discoloring fungi include Aureobasidium pullulans, Sclerov pithiophila, Scopular phycomyces, and Aspergillus niger. Penicillium pinophilum, Trichoderma virens, Trichoderma viride, Trichoderma lignorum, Trichoderma rignumum · Fusarioidesu (Dactyleum fusarioides), Karatoshisutesu - seminar (Caratocystis minor), Rhizopus oryzae (Rhizopus oryzae), include Mucor Supinosasu (Mucor spinosus) and the like.

The compound of the present invention is an oil agent, emulsion, liquid agent, microemulsion agent, aqueous suspension preparation, for wood preservation, for sterilization for wood preservation, and for antiseptic and antifungal for wood preservation. It can be used as a dosage form such as an aqueous emulsion preparation, a suspoemulsion preparation, a microcapsule preparation, a wettable powder, a granular wettable powder, a water solvent, a granular water solvent, and a powder. As long as an effect is exhibited, it is not limited to those dosage forms.
The wood preservative, the wood preservative, and the wood preservative / antifungal agent of the present invention can be in the above-mentioned dosage forms.

Specific formulation examples are shown below, but are not limited thereto.
[Formulation Example 1 Emulsion]
An emulsion is obtained by uniformly stirring and mixing 10 parts of the pyridone compound according to the present invention, 6 parts of polyoxyethylene styryl phenyl ether and 84 parts of solvent naphtha.
[Formulation Example 2 Flowable Agent]
10 parts of pyridone compound according to the present invention, 5 parts of sodium salt of formaldehyde condensate of naphthalene sulfonic acid, 1 part of polyoxyethylene arylphenyl ether, 5 parts of propylene glycol, 0.1 part of silicon-based antifoaming agent, 0.2% of xanthan gum Part and 78.7 parts of ion-exchanged water are mixed to form a slurry, and further wet pulverized with Dynomill KDL using glass beads with a diameter of 1.0 mm to obtain a flowable agent.
[Formulation Example 3 wettable powder]
10 parts of pyridone compound according to the present invention, 10 parts of white carbon, 2 parts of polyvinyl alcohol, 0.5 part of sodium dioctylsulfosuccinate, 5 parts of sodium salt of alkylbenzene sulfonate, 10 parts of calcined diatomaceous earth and 62.5 parts of kaolinite clay Are thoroughly mixed and ground with an air mill to obtain a wettable powder.

As a method for treating the compound of the present invention for wood preservation, for sterilization for wood preservation, and for antiseptic / antifungal for wood preservation, a conventional wood preservation treatment method for woody materials is used. It can be applied in a similar manner. Surface treatment (application, spraying, dipping, etc.), deep infiltration treatment, pressure injection treatment, adhesive mixing treatment, etc. are usually performed at wooden buildings or their construction sites, wood material manufacturing factories, wood preservation processing factories, etc. It can be applied to any of these.

The “woody material” as used in the present invention is a material obtained by subjecting wood and wood to mechanical processing and adhesive molding processing. For example, logs, lumber, laminated wood, plywood, veneer laminate (LVL), orientation Examples include strand boards (OSB), particle boards, various fiber boards (insulation boards, medium density fiber plates (MDF), hard boards), and the like.

The treatment amount of the compound of the present invention varies depending on the target wood material, treatment method, and the like. However, when surface treatment for attaching a chemical solution to the surface of the material is performed, the amount of active ingredient per 1 m ² of the surface area of the wood material. 0.001 to 10 g is suitable, and preferably 0.01 to 1 g per 1 m ² . In addition, the amount of treatment in the case of deep infiltration treatment for infiltrating the chemical into the material, pressure injection treatment, adhesive mixing treatment, etc. is 0.01 to 1,000 g per 1 m ³ of wood material volume as the active ingredient amount. Yes, preferably 1 to 100 g per m ³ .

The wood preservative, the wood preservative of the present invention, and the wood preservative antiseptic / antifungal agent can be used as a wood preservative, pesticide, synergist as long as the effect is exhibited, if necessary. It may further contain one or more other antibiotic active compounds such as an agent.

As the fungicide, for example, F-69 (2- (2,4-difluorophenyl) -1- (1H-1,2,4-triazol-1-yl) -3- (trimethylsilyl) propan-2-ol ), Tebuconazole, propiconazole, cyproconazole, hexaconazole, epoxiconazole, ipconazole, metconazole, prochlorazole, azaconazole and other azole compounds, diiodomethyl-p-tolylsulfone, 3-iodo-2-propynylbutyl Carbamate, iodo compounds such as 4-chlorophenyl-3-iodopropargyl formal, 4-methoxyphenyl-3-iodopropargyl formal, triiodoallyl alcohol, mepronil, flutolanil, furamethpyr, boscalid, mycole, tifluzamide Benodanyl, fenflam, carboxin, oxycarboxyl, isotianil, teclophthalam, mevenyl, fluorophene, pyracarbollide, furcarbanil, metofloxam, penflufen, bixafen and other acid anilide compounds, cupric oxide, cupric hydroxide, copper sulfate, Compounds containing copper such as copper naphthenate and copper octylate, compounds containing zinc such as zinc naphthenate, zinc versatate and zinc octylate or didecyldimethylammonium chloride, didecyldimethylammonium bicarbonate / carbonate , Quaternary ammonium salt compounds such as didecyldimethylammonium propionate, benzalkonium chloride, benzimidazole series, isothiazoline series, 2- (4-thiocyanomethylthio) benzothiazole, methylene Wood preservatives fungicides such as Suchioshianeto and the like.

Insecticides include dd-T-cyphenothrin, acrinathrin, permethrin, phenothrin, d-phenothrin, allethrin, d-arethrin, dd-alleslin, pyrethrin, praretrin, ciphenothrin, cyfluthrin, beta-cyfluthrin, bifenthrin, cycloprotorin , Cyhalothrin, Lambda Cyhalothrin, Gamma Cyhalothrin, Cypermethrin, Sigma Cipermethrin, Alpha Cypermethrin, Zetacypermethrin, Dimefluthrin, Empentrin, Deltamethrin, Terrareslin, Tefluthrin, Fenvalerate, Esfenvalerate, Flucitrinate, Full Fenprox, flumethrin, fulvalinate, taufulvalinate, profluthrin, halfenprox, imiprotorin, benfurthuri Pyrethroid compounds such as phenmethrin, resmethrin, d-resmethrin, silafluophene, tralomethrin, tetramethrin, d-tetramethrin, framethrin, methfluthrin, phenpropatoline, transfluthrin, etofenprox, acephate, butathiophos, chlorethoxyphos, chlorfenbin Phos, Chlorpyrifos, Chlorpyrifosmethyl, Cyanophos, Diazinon, DCIP, Diclofenthion, Dichlorvos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Etoprophos, Etrimphos, Fentione, Fenitrothion, Phostiazeto, Formothione, Isofenphos, Isoxathione, Sulthiomethione, Sulthiomethione , Monocrotofos, Nared, Parathion, Salon, phosmet, pyrimiphosmethyl, pyridafenthion, quinalphos, phentoate, propenophos, propaphos, prothiophos, pyracrofos, salicione, sulprophos, temefos, terbufos, trichlorfone, phenylpyrazole compounds such as fipronil, pyriprole, propoxol, Alanicarb, Benfuracarb, BPMC, Carbaryl, Carbofuran, Carbosulfuran, Chloetocarb, Ethiophenecarb, Fenobucarb, Mesomil, Methiocarb, NAC, Oxamyl, Pirimicarb, XMC, Carbamate compounds such as Thiodicarb, Xilicarb, Aldicarb, Oxadiazol, etc. Compound, imidacloprid, clothianidin, thiameth Neonicotinoid compounds such as xham, dinotefuran, acetamiprid, nitenpyram, thiacloprid, pyriproxyfen, metoprene, hydroprene, phenoxycarb, etoxazole, chlorfluazuron, triazurone, novallon, hexaflumuron, diflubenzuron, cyromazine, flufenoc Insect growth regulators such as throne, teflubenzuron, triflumuron, lufenuron, macrolide compounds such as milbemycin, abamectin, ivermectin, chlorantraniliprole, cyantraniliprolol, cyclaniliprol, tetraniliprol, fulvendiamide, cyhalodiamide And diamide compounds such as brofuranilide and fluxamethamide.

Examples of synergists include piperonyl butoxide, O-propargyl-O-propylphenylphosphonate (NIA16388), isobornyl thiocyanoacetate (IBTA), N- (2-ethylhexyl) -bicyclo [2.2.1. ] -Hepta-5-ene-2,3-dicarboximide (MGK-264), 2,2 ′, 3,3,3,3 ′, 3 ′, 3′-octachlorodipropyl ether (S-421) ), Sinepiline 500, propyl isome, piperonylcyclone, sesamolin, sesamex, sesamin, sulfoxide, safroxan, benzyl benzoate and the like.

The mixing ratio of the other antibiotic active compound and the compound according to the present invention is usually 0.01: 1000 to 1000: 1, preferably 0.1: 100 to 500: 1, in mass ratio. In addition, the other antibiotic active compounds described above may be prepared separately from the compound of the present invention, and used in combination with the woody material.
The wood preservative, wood preservative, and wood preservative / antifungal agent of the present invention may contain conventional additives in addition to the compound of the present invention and the above-mentioned antibiotic compounds.

Hereinafter, the present invention will be described in more detail with reference to synthesis examples, reference examples, and test examples, but the present invention is not limited thereto.

[Synthesis Example 1]
Step 1: Synthesis of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -3,4-dihydropyridin-2 (1H) -one

10 ml of an acetic acid solution containing 1.47 g of 4- (2-chloro-5-methoxyphenyl) -5- (2,6-difluorophenyl) -5-oxopentanoic acid and 6.75 g of ammonium acetate was added at 130 ° C. Reacted for hours. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture for liquid separation. Water was added to the obtained organic layer, and potassium carbonate was further added until the firing was stopped, followed by liquid separation. Next, the organic layer was washed with saturated brine and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the precipitate was washed with diisopropyl ether. The resulting purple solid was the title compound, 0.98 g.
¹ H-NMR (CDCl ₃ ) δ: 7.25-7.21 (1H, m), 7.19 (1H, d, J = 8.8 Hz), 6.83-6.76 (3H, m ), 6.65 (1H, dd, J = 8.8, 3.4 Hz), 6.53 (1H, d, J = 3.4 Hz), 3.61 (3H, s), 2.91 -2.76 (4H, m).

Step 2: Synthesis of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethyl-3,4-dihydropyridin-2 (1H) -one (Compound No. 52)

5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -3,4-dihydropyridin-2 (1H) -one in 5 ml of DMF solution containing 0.50 g and 346 μl of ethyl iodide And 1.41 g of cesium carbonate were added and stirred at 60 ° C. for 2 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 0.54 g of a white solid.

[Synthesis Example 2]
Synthesis of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 53)

To 20 ml of a carbon tetrachloride solution containing 520 mg of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethyl-3,4-dihydropyridin-2 (1H) -one, N-bromosuccinimide (258 mg) and azobisisobutyronitrile (23 mg) were added, and the mixture was stirred at 80 ° C. for 90 minutes. After cooling to room temperature, water was added to the reaction mixture, and carbon tetrachloride was distilled off under reduced pressure. Ethyl acetate was added thereto for liquid separation, and the obtained organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 467 mg of a white solid.

[Synthesis Example 3]
Synthesis of 3-chloro-5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 54)

Add 43 mg of N-chlorosuccinimide to 2 ml of DMF solution containing 110 mg of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one , And stirred at 70 ° C. for 1 hour. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture for liquid separation. The obtained organic layer was washed with saturated brine, and then dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 114 mg of a white solid.

[Synthesis Example 4]
Synthesis of 5- (2-chloro-5-hydroxyphenyl) -6- (2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 234)

40 ml of a dichloromethane solution containing 4.0 g of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one was ice-cooled. 23.4 ml of a dichloromethane solution of 0 mol / l boron tribromide was added dropwise. After stirring for 30 minutes under ice cooling, water was added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with an aqueous sodium thiosulfate solution and a saturated aqueous sodium bicarbonate solution, and dried over sodium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was washed with hexane. The title compound was obtained as 3.9 g of a white solid.

[Synthesis Example 5]
Synthesis of 5- (2-chloro-5- (methoxymethoxy) phenyl) -6- (2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 97)

Sodium hydride (approximately 60% by weight, dispersed in liquid paraffin) 0.08 g and 5- (2-chloro-5-hydroxyphenyl) -6- (2,6-difluorophenyl) -1-ethylpyridine-2 0.08 g of chloromethyl methyl ether was added to a THF solution containing 0.62 g of (1H) -one, and the mixture was stirred at room temperature for 3 hours. Water and ethyl acetate were added to the reaction mixture for liquid separation, and the obtained organic layer was dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 0.46 g of a white solid.

[Synthesis Example 6]
Synthesis of 3-chloro-5- (2-chloro-5- (methoxymethoxy) phenyl) -6- (2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 127)

3-ml DMF solution containing 219 mg 5- (2-chloro-5- (methoxymethoxy) phenyl) -6- (2,6-difluorophenyl) -1-ethylpyridin-2 (1H) -one and 79 mg N-chlorosuccinimide Was stirred at 70 ° C. for 1 hour. After cooling to room temperature, a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 203 mg of a yellow gum.

[Synthesis Example 7]
Synthesis of 5- (2-chloro-5-methoxyphenyl) -1- (2,2-difluoroethyl) -6- (2,6-difluorophenyl) -3,4-dihydropyridin-2 (1H) -one Compound No. 192)

5- (2-Chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -3,4-dihydropyridin-2 (1H) -one 0.50 g, 2,2-difluoro p-toluenesulfonic acid 10 ml of a DMF solution containing 0.68 g of ethyl and 1.40 g of cesium carbonate was stirred at 80 ° C. for 4 hours. Water and ethyl acetate were added to the reaction mixture for liquid separation, and the obtained organic layer was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 0.48 g of a white solid.

[Synthesis Example 8]
Synthesis of 5- (2-chloro-5-methoxyphenyl) -1- (2,2-difluoroethyl) -6- (2,6-difluorophenyl) pyridin-2 (1H) -one (Compound No. 194)

5- (2-Chloro-5-methoxyphenyl) -1- (2,2-difluoroethyl) -6- (2,6-difluorophenyl) -3,4-dihydropyridin-2 (1H) -one 0.42 g N-bromosuccinimide 190 mg and azobisisobutyronitrile 16 mg were added to a carbon tetrachloride solution containing 15 ml, and the mixture was stirred at 80 ° C. for 15 minutes. After cooling to room temperature, water was added to the reaction mixture, and carbon tetrachloride was distilled off under reduced pressure. Ethyl acetate was added thereto for liquid separation, and the obtained organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 0.38 g of a white solid.

[Synthesis Example 9]
Synthesis of 3-bromo-5- (2-chloro-5-methoxyphenyl) -1- (2,2-difluoroethyl) -6- (2,6-difluorophenyl) pyridin-2 (1H) -one (compound Number 198)

5- (2-chloro-5-methoxyphenyl) -1- (2,2-difluoroethyl) -6- (2,6-difluorophenyl) pyridin-2 (1H) -one (125 mg) and N-bromosuccinimide (65 mg) The DMF solution containing 5 ml was stirred at 70 ° C. for 2 hours. To this was added 27 mg of N-bromosuccinimide, and the mixture was further stirred at 70 ° C. for 2 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 109 mg off-white solid.

[Synthesis Example 10]
Synthesis of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethyl-3-methyl-3,4-dihydropyridin-2 (1H) -one

10 ml of a THF solution containing 500 mg of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethyl-3,4-dihydropyridin-2 (1H) -one at −78 ° C. Then, 1.33 ml of a THF solution of 1.09 mol / l lithium diisopropylamide was added dropwise and stirred at the same temperature for 30 minutes. Next, 2 ml of a THF solution containing 82 μl of methyl iodide was added dropwise thereto, followed by stirring at −78 ° C. for 2 hours, and then the temperature was raised to room temperature. After further stirring at room temperature for 2 hours, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 101 mg of a white solid. The obtained title compound was a stereoisomeric mixture.
¹ H-NMR (CDCl ₃ ) δ: 7.24-7.17 (1H, m: mixure), 7.15-7.13 (1H, m: mixure), 6.87-6.71 (2H, m: mixture), 6.57-6.49 (2H, m: mixture), 3.70-3.14 (2H, m: mixture), 3.65 (3H, s: major), 3.58 ( 3H, s: minor), 2.98-2.70 (2H, m: mixture), 2.46-2.37 (1H, m: mixture), 1.35 (3H, d, J = 6.7). Hz: minor), 1.33 (3H, d, J = 7.0 Hz: major), 1.00-0.96 (3H, m).
Stereoisomeric mixture ratio: about 57:43

[Synthesis Example 11]
Synthesis of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethyl-3-methylpyridin-2 (1H) -one (Compound No. 329)

4. 413 mg of 5- (2-chloro-5-methoxyphenyl) -6- (2,6-difluorophenyl) -1-ethyl-3-methyl-3,4-dihydropyridin-2 (1H) -one and manganese dioxide 10 ml of a dichloromethane solution containing 48 g was stirred for 11 hours under heating and reflux. Further, 1.83 g of manganese dioxide was added, and the mixture was stirred for 3 hours with heating under reflux. After cooling to room temperature, the reaction mixture was filtered through celite. After the solvent was distilled off from the filtrate under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 291 mg of a white solid.

[Synthesis Example 12]
Step 1: Synthesis of 5- (2-chloro-5-fluorophenyl) -6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one

25 ml of acetic acid solution containing 4.46 g of 4- (2-chloro-5-fluorophenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoic acid and 45.9 g of ammonium acetate at 130 ° C. Stir for 2 hours. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture for liquid separation. Water was added to the obtained organic layer, and potassium carbonate was further added until foaming stopped, followed by liquid separation. Next, the organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the precipitate was washed with diisopropyl ether. The resulting white solid was the title compound, 2.24 g. Further, the filtrate produced when the precipitate was washed was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The white solid obtained from the filtrate was also the title compound, 0.46 g.
¹ H-NMR (CDCl ₃ ) δ: 7.28-7.26 (1H, m), 7.18 (1H, br s), 6.86-6.83 (1H, m), 6.74- 6.72 (1H, m), 6.61-6.59 (2H, br m), 2.85-2.74 (4H, br m).

Step 2: Synthesis of 5- (2-chloro-5-fluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one (compound Number 320)

5- (2-chloro-5-fluorophenyl) -6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one 2.70 g, cesium carbonate 7.42 g and iodine 32 ml of DMF solution containing 3.55 g of ethyl chloride was stirred at 55 ° C. for 2 hours. After cooling to room temperature, ethyl acetate and water were added to the reaction mixture for liquid separation. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 2.47 g of a magenta gum.

[Synthesis Example 13]
Synthesis of 5- (2-chloro-5-fluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 321)

5- (2-chloro-5-fluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one 0.21 g and manganese dioxide 1 5 ml of a toluene solution containing .42 g was stirred at 90 ° C. for 5 hours. After cooling to room temperature, the reaction mixture was filtered through celite. After the solvent was distilled off from the filtrate under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 0.14 g of a white solid.

[Synthesis Example 14]
Synthesis of 3-bromo-5- (2-chloro-5-fluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 381)

5- (2-chloro-5-fluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (0.60 g) and N-bromosuccinimide (0.33 g) 30 ml of the DMF solution contained was stirred at 75 ° C. for 2.5 hours. Further, 0.10 g of N-bromosuccinimide was added and stirred at 75 ° C. for 1.5 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed with saturated brine, and then dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 0.64 g of a white solid.

[Synthesis Example 15]
Synthesis of 5- (2-chloro-5-fluorophenyl) -1-ethyl-3-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 461)

3-Bromo-5- (2-chloro-5-fluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one 250 mg, methylboronic acid 49 mg, palladium acetate (II) A mixed solution of 8 ml of toluene and 0.8 ml of water containing 6 mg, 403 mg of tripotassium phosphate and 15 mg of tricyclohexylphosphine was stirred at 100 ° C. for 7 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed with saturated brine, and then dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 116 mg of a white solid.

[Synthesis Example 16]
Synthesis of 3-bromo-5- (2-chloro-5-fluorophenyl) -6- (2,6-difluoro-4-methoxyphenyl) -1-ethylpyridin-2 (1H) -one (Compound No. 476)

3-Bromo-5- (2-chloro-5-fluorophenyl) -1-ethyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one 28 mg in 8 ml of 300 mg methanol solution 0.63 ml of a methanol solution of% sodium methoxide was added, and the mixture was stirred for 13 hours under heating and reflux. After cooling to room temperature, a saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 271 mg of a white solid.

[Synthesis Example 17]
Step 1: Synthesis of 5- (3,5-dimethoxyphenyl) -6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one

To the crude 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoic acid obtained in Reference Example 3, 14.18 g of ammonium acetate and 15 ml of acetic acid And stirred at 120 ° C. for 10 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, isopropyl ether was added to the obtained solid and washed. The title compound was obtained as a 0.99 g brown solid.
¹ H-NMR (CDCl ₃ ) δ: 6.68 (1H, s), 6.62 (2H, td, J = 8.7, 1.4 Hz), 6.26 (1H, t, J = 2) .1 Hz), 6.16 (2H, d, J = 2.1 Hz), 3.65 (6H, s), 2.87-2.86 (2H, m), 2.73-2.71 (2H, m).

Step 2: Synthesis of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one

5- (3,5-dimethoxyphenyl) -6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one 343 mg, methyl iodide 176 μl and cesium carbonate 1.85 g 6 ml of the DMF solution was stirred for 3 hours at room temperature. Water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with water, aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 346 mg of a white solid.
¹ H-NMR (CDCl ₃ ) δ: 6.62-6.60 (2H, m), 6.23 (1H, t, J = 2.1 Hz), 6.13 (2H, d, J = 2) .1 Hz), 3.65 (6H, s), 2.87 (3H, s), 2.76-2.74 (4H, m).

[Synthesis Example 18]
Synthesis of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 134)

Contains 320 mg of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) -3,4-dihydropyridin-2 (1H) -one and 4.42 g of manganese dioxide 12 ml of a dichloromethane solution was stirred for 5 hours under heating to reflux. After cooling to room temperature, the reaction mixture was filtered through celite. After the solvent was distilled off from the filtrate under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 263 mg of a white solid.

[Synthesis Example 19]
Synthesis of 5- (2-chloro-3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one (Compound No. 136)

6 ml of a DMF solution containing 163 mg of 5- (3,5-dimethoxyphenyl) -1-methyl-6- (2,4,6-trifluorophenyl) pyridin-2 (1H) -one and 64 mg of N-chlorosuccinimide, Stir at 80 ° C. for 5 hours. Further, 45 mg of N-chlorosuccinimide was added and stirred at 100 ° C. for 4 hours. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with aqueous sodium thiosulfate solution and saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 150 mg of a white solid.

<Reference Example 1>
Step 1: Synthesis of 2- (2-chloro-5-methoxyphenyl) -1- (2,6-difluorophenyl) ethanone

After cooling 30 ml of a THF solution containing 2.05 g of 2- (2-chloro-5-methoxyphenyl) acetic acid to −78 ° C., 17.21 ml of a THF solution of 1.9 mol / L hexamethyldisilazane sodium was added to −50 The solution was added dropwise at not more than 0 ° C. and stirred at −78 ° C. for 40 minutes. To this was added dropwise 10 ml of a THF solution containing 1.76 g of methyl 2,6-difluorobenzoate at −78 ° C., and then the mixture was warmed to room temperature and stirred for 1.5 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture and stirred, and then ethyl acetate was added to separate the layers. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the title compound as 2.58 g of a yellow oily substance.
¹ H-NMR (CDCl ₃ ) δ: 7.40-7.38 (1H, m), 7.28-7.27 (1H, m), 6.96-6.94 (2H, m), 6 .83 (1H, d, J = 3.1 Hz), 6.78 (1H, dd, J = 8.9, 3.1 Hz), 4.27 (2H, s), 3.79 (3H, s).

Step 2: Synthesis of ethyl 4- (2-chloro-5-methoxyphenyl) -5- (2,6-difluorophenyl) -5-oxopentanoate

2- (2-Chloro-5-methoxyphenyl) -1- (2,6-difluorophenyl) ethanone To 15 ml of a THF solution containing 1.30 g, 98 mg of potassium t-butoxide and 525 μl of ethyl acrylate were added, and the mixture was ice-cooled. Stirred overnight. 1N Hydrochloric acid and ethyl acetate were added to the reaction mixture for liquid separation, and the obtained organic layer was washed with saturated brine and dried over sodium sulfate. After evaporating the solvent under reduced pressure, the title compound was obtained as 1.69 g of a yellow oil. Used in the next reaction without further purification.
¹ H-NMR (CDCl ₃ ) δ: 7.36-7.25 (1H, m), 7.19 (1H, d, J = 8.9 Hz), 6.83 (2H, t, J = 8 .1 Hz), 6.74-6.71 (2H, m), 4.91 (1H, t, J = 7.2 Hz), 4.13 (2H, q, J = 7.1 Hz), 3.76 (3H, s), 2.57-2.53 (1H, m), 2.42-2.29 (2H, m), 2.16-2.07 (1H, m), 25 (3H, t, J = 7.1 Hz).

Step 3: Synthesis of 4- (2-chloro-5-methoxyphenyl) -5- (2,6-difluorophenyl) -5-oxopentanoic acid

4- (2-Chloro-5-methoxyphenyl) -5- (2,6-difluorophenyl) -5-oxopentanoic acid ethyl 1.69 g of THF mixed with 40 ml of THF and 10 ml of water were mixed with lithium hydroxide 1 The hydrate 0.74g was added and it stirred at 60 degreeC for 3 hours. After cooling to room temperature, the solvent of the reaction mixture was distilled off until the liquid volume became about half. Water and diethyl ether were added thereto for liquid separation, and the obtained aqueous layer was separated by adding concentrated hydrochloric acid and ethyl acetate. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. Then after distilling off the solvent under reduced pressure, the title compound was obtained as 1.47 g of a yellow gum. Used in the next reaction without further purification.
¹ H-NMR (CDCl ₃ ) δ: 7.28-7.27 (1H, m), 7.19 (1H, d, J = 8.6 Hz), 6.83 (2H, t, J = 8 .3 Hz), 6.75-6.74 (1H, m), 6.71 (1H, dd, J = 8.6, 3.1 Hz), 4.92 (1H, t, J = 7. 3 Hz), 3.75 (3H, s), 2.60-2.34 (3H, m), 2.15-2.12 (1H, m).

<Reference Example 2>
Step 1: Synthesis of N ′-(2-chloro-5-fluorobenzylidene) -4-methylbenzenesulfonyl hydrazide

250 ml of an ethanol solution containing 25.43 g of 2-chloro-5-fluorobenzaldehyde and 29.87 g of 4-methylbenzenesulfonyl hydrazide was stirred at room temperature for 4 hours. The reaction mixture was then stirred for 1 hour under ice cooling and the precipitate was filtered to give the title compound as 40.74 g of a white solid.
¹ H-NMR (CDCl ₃ ) δ: 8.27 (1H, s), 8.10 (1H, d, J = 1.8 Hz), 7.88 (2H, d, J = 8.2 Hz) 7.58 (1H, dd, J = 9.2, 3.1 Hz), 7.34 (2H, d, J = 8.2 Hz), 7.30-7.28 (1H, m), 7.02-6.99 (1H, m), 2.43 (3H, s).

Step 2: Synthesis of 2- (2-chloro-5-fluorophenyl) -1- (2,4,6-trifluorophenyl) ethanone

To 600 ml of an aqueous solution containing 4.0 g of sodium hydroxide, 32.7 g of N ′-(2-chloro-5-fluorobenzylidene) -4-methylbenzenesulfonylhydrazide and 8.0 g of 2,4,6-trifluorobenzaldehyde were added. And stirred at 80 ° C. for 1 hour. After cooling to room temperature, ethyl acetate and 15.0 g of ammonium chloride were added to the reaction mixture, and the mixture was stirred and separated. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 6.13 g of a pale yellow solid.
¹ H-NMR (CDCl ₃ ) δ: 7.36-7.34 (1H, m), 7.04-7.02 (1H, m), 6.98-6.96 (1H, m), 6 .76-6.72 (2H, m) 4.26 (2H, s).

Step 3: Synthesis of ethyl 4- (2-chloro-5-fluorophenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoate

75 ml of THF solution containing 6.13 g of 2- (2-chloro-5-fluorophenyl) -1- (2,4,6-trifluorophenyl) ethanone was ice-cooled, 0.45 g of potassium t-butoxide and acrylic acid Ethyl 2.23g was added and it stirred at room temperature for 8 hours. After 10% hydrochloric acid was added to the reaction mixture, water and ethyl acetate were added to separate the layers. The obtained organic layer was washed with saturated brine, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 4.97 g of a pale yellow oil. ¹ H-NMR (CDCl ₃ ) δ: 7.30 (1H, dd, J = 8.9, 5.2 Hz), 7.01-6.98 (1H, m), 6.92-6.90 (1H, m), 6.66-6.60 (2H, m), 4.89 (1H, t, J = 7.2 Hz), 4.13 (2H, q, J = 7.2 Hz) , 2.54-2.52 (1H, m), 2.35-2.31 (2H, m), 2.12-2.09 (1H, m), 1.25 (3H, t, J = 7.2 Hz).

Step 4: Synthesis of 4- (2-chloro-5-fluorophenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoic acid

4- (2-chloro-5-fluorophenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoate 4.97 g in THF solution 100 ml, water 25 ml and lithium hydroxide 1 2.59 g of hydrate was added and stirred at 60 ° C. for 2 hours. After cooling to room temperature, the reaction mixture was evaporated under reduced pressure. Water and diethyl ether were added thereto for liquid separation. Next, the obtained aqueous layer was acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the title compound was obtained as 4.46 g of a colorless transparent gum. Used in the next reaction without further purification.
¹ H-NMR (CDCl ₃ ) δ: 7.32-7.29 (1H, m), 7.00-6.97 (1H, m), 6.94-6.89 (1H, m), 6 .64-6.60 (2H, m), 4.89 (1H, t, J = 7.2 Hz), 2.58-2.06 (4H, m).

<Reference Example 3>
Step 1: Synthesis of N ′-(3,5-dimethoxybenzylidene) -4-methylbenzenesulfonyl hydrazide

100 ml of an ethanol solution containing 10.0 g of 3,5-dimethoxybenzaldehyde and 11.2 g of 4-methylbenzenesulfonyl hydrazide was stirred at room temperature for 5 hours. The resulting reaction mixture was evaporated under reduced pressure to give the title compound as 20.0 g of a yellow solid.
¹ H-NMR (CDCl ₃ ) δ: 8.13 (1H, s), 7.87 (2H, d, J = 7.8 Hz), 7.68 (1H, s), 7.30 (2H, d, J = 7.8 Hz), 6.72 (2H, d, J = 2.4 Hz), 6.46 (1H, t, J = 2.4 Hz), 3.79 (6H, s) , 2.40 (3H, s).

Step 2: Synthesis of 2- (3,5-dimethoxyphenyl) -1- (2,4,6-trifluorophenyl) ethanone

20 ml of an aqueous solution in which 0.80 g of sodium hydroxide is dissolved in 100 ml of an aqueous solution containing 6.68 g of N ′-(3,5-dimethoxybenzylidene) -4-methylbenzenesulfonylhydrazide and 2,4,6-trifluorobenzaldehyde 60 g was added and stirred at 80 ° C. for 90 minutes. After cooling to room temperature, ethyl acetate was added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with saturated aqueous ammonium chloride solution and saturated brine, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 1.85 g of a yellow oil.
¹ H-NMR (CDCl ₃ ) δ: 6.68-6.66 (2H, m), 6.35 (3H, s), 4.06 (2H, s), 3.75 (6H, s).

Step 3: Synthesis of ethyl 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoate

To 18 ml of THF solution containing 1.85 g of 2- (3,5-dimethoxyphenyl) -1- (2,4,6-trifluorophenyl) ethanone, 67 mg of potassium t-butoxide and 714 μl of ethyl acrylate were added, and iced. Stir overnight under cold. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture to separate the layers. The obtained organic layer was washed with saturated brine, and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography. The title compound was obtained as 1.51 g of a brown oil.
¹ H-NMR (CDCl ₃ ) δ: 6.61-6.57 (2H, m), 6.31-6.29 (3H, m), 4.19 (1H, t, J = 7.3 Hz ), 4.13 (2H, q, J = 7.1 Hz), 3.73 (6H, s), 2.49-2.47 (1H, m), 2.30 (2H, t, J = 7.5 Hz), 2.09-2.07 (1H, m), 1.25 (3H, t, J = 7.1 Hz)

Step 4: Synthesis of 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoic acid

15 ml of acetic acid solution containing 1.51 g of ethyl 4- (3,5-dimethoxyphenyl) -5-oxo-5- (2,4,6-trifluorophenyl) pentanoate and 3 ml of concentrated hydrochloric acid is stirred at 60 ° C. for 3 hours. did. After cooling to room temperature, water and ethyl acetate were added to the reaction mixture for liquid separation. The obtained organic layer was washed successively with water and saturated brine, and dried over sodium sulfate. The solvent was distilled off under reduced pressure to give the title compound. Used in the next step reaction without further purification.

Although the compound synthesize | combined according to the above-mentioned Example is shown in Table 4, this invention compound is not limited to these.
Structure A represents:

Structure B represents the following:

Structure C represents:

Structure D represents:

Next, for the compounds described in Table 4, their ¹ H-NMR data are shown in Table 5.

Next, the compound of the present invention is specifically shown to be effective against wood decay fungi, but is not limited to these examples.

[Test Example A] Kawaratake (Trametes versicolor)
The compound according to the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solvent (volume ratio: 1/9) to obtain a 0.05% w / v chemical solution. 10 ml of potato dextrose agar medium was poured into a petri dish having a diameter of 90 mm, and 10 μl of a chemical solution was added and stirred well, and then allowed to stand at room temperature. As a control, a potato dextrose agar medium containing only a solvent was prepared in the same manner. After the medium was solidified, the bacterial flora was inoculated at both ends of the test medium with a cork borer having a diameter of 4 mm from a colony of Trametes versicolor, a wood-rotting fungus previously cultured. The petri dish was cultured at 26 ° C., and the radius of the colony that spread from the inoculation source was measured on the 6th to 7th days to evaluate the effect of the compound according to the present invention.

[Test Example B] Japanese cypress (Fomitopsis palustris)
The compound according to the present invention was dissolved in a dimethyl sulfoxide-methanol mixed solvent (volume ratio: 1/9) to obtain a 0.05% w / v chemical solution. 10 ml of potato dextrose agar medium was poured into a petri dish having a diameter of 90 mm, and 10 μl of a chemical solution was added and stirred well, and then allowed to stand at room temperature. As a control, a potato dextrose agar medium containing only a solvent was prepared in the same manner. After the medium was solidified, the flora was excised from the colony of Fomitopsis palustris, a wood-rotting fungus previously cultured, with a 4 mm diameter cork borer and inoculated at both ends of the test medium. The petri dish was cultured at 26 ° C., and the radius of the colony that spread from the inoculation source was measured on the 6th to 7th days to evaluate the effect of the compound according to the present invention.

From the above test results, the growth inhibition rate of the fungus compared with the radius of the control colony was determined by the following formula and expressed as the degree of inhibition. The results of Test Example A and Test Example B are shown in Tables 6 and 7.
Growth inhibition rate (%) = {(radius of control colony−radius of colony in test area) / radius of control colony}
Degree of inhibition ◎: Growth inhibition rate 75% or more ○: Growth inhibition rate 50% or more and less than 75% △: Growth inhibition rate 25% or more and less than 50%

The pyridone compound according to the present invention is a novel compound, and can exert a controlling activity against wood decaying fungi or wood discoloring fungi to prevent biological deterioration of the woody material. , And useful as a preservative and fungicide for wood preservation.

Claims

Formula (1)

[Wherein R1 is a hydroxyl group,
A cyano group,
A C1-C6 alkyl group optionally substituted with substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with the substituent A,
A C2-C6 alkenyl group optionally substituted with the substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with substituent A,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with the substituent A,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with the substituent A,
A C2-C6 alkenyloxy group optionally substituted with the substituent A,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with the substituent A,
A C3-C6 haloalkynyloxy group,
Or R10R11N— (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group);
R2 is a halogen atom,
Hydroxyl group,
A cyano group,
Nitro group,
A C1-C6 alkyl group optionally substituted with the substituent B,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with the substituent B,
A C2-C6 alkenyl group optionally substituted with the substituent B,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with substituent B,
A C2-C6 haloalkynyl group,
A C1-C6 alkoxy group optionally substituted with the substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with the substituent B,
A C2-C6 alkenyloxy group optionally substituted with the substituent B,
A C2-C6 haloalkenyloxy group,
A C3-C6 alkynyloxy group optionally substituted with the substituent B,
A C3-C6 haloalkynyloxy group,
R20C (═O) — (wherein R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, A C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, a C1-C6 Represents a haloalkyl group, or a C3-C8 cycloalkyl group, or R21 and R22, together with the nitrogen atom to which they are attached, represents an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group. Represents what is to be formed.)
R20C (═O) O— (wherein R20 has the same meaning as above),
A 3- to 6-membered group containing 1 to 2 oxygen atoms,
R23-L2- (wherein, R23 represents a C1 alkyl group ~ C6 or C1 ~ C6 haloalkyl group,, L2 represents S, SO, or SO 2.),
R21R22N- (wherein R21 and R22 are as defined above),
Or R24C (═O) N (R25) — (wherein R24 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, or R21R22N— (wherein R21 and R22 have the same meanings as described above), and R25 is optionally substituted with a hydrogen atom or substituent B1. Represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, which may be
R3 is a hydrogen atom,
Halogen atoms,
Nitro group,
A C1-C6 alkyl group optionally substituted with substituent C,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with substituent C,
A C1-C6 alkoxy group that may be optionally substituted with a substituent C;
A C1-C6 haloalkoxy group,
A C2-C6 alkenyl group optionally substituted with substituent C,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with substituent C,
A C2-C6 haloalkynyl group,
R30-L3- (wherein R30 has the same meaning as R23 above, and L3 has the same meaning as L2 above),
R31R32N- (wherein R31 and R32 have the same meanings as R21 and R22 above),
Or R33C (═O) — (wherein R33 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group);
n represents an integer of 0 to 5 (provided that when n is 2 or more, R 2 of 2 or more represents an independent substituent);
X represents an oxygen atom or a sulfur atom;
Y represents a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, or a thiadiazolyl group;
In the phenyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 4 appropriately,
In the pyridyl group, the pyrazinyl group, the pyrimidinyl group, the pyridazinyl group, the triazinyl group, or the tetrazinyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently selected from 0 to 3 Replace
In the thienyl group, the thiazolyl group, the isothiazolyl group, or the thiadiazolyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 2 appropriately;
A bond including a broken line part represents a double bond or a single bond,
And the substituent A is
Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, R12R13N- (wherein R12 and R13 are each independently Each represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C3-C8 cycloalkyl group, or R12 and R13 together with the nitrogen atom to which they are attached, is an aziridinyl group , An azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group), and R14-L1- (wherein R14 is a C1-C6 alkyl group or a C1-C6 haloalkyl group) represents a group, is selected L1 is, S, SO, or from the group consisting of.) representing the SO 2, At least one selected from;
Substituent B is
Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, C2-C6 alkoxyalkoxy group, R21R22N- R21 and R22 are as defined above), R23-L2- (where R23 and L2 are as defined above), R26R27R28Si— (wherein R26, R27 and R28 are each independently And represents an alkyl group of C1 to C6), R26R27R28Si— (CH 2 ) s—O— (wherein s represents an integer of 1 to 3, and R26, R27 and R28 are as defined above) ), R20C (═O) — (wherein R20 is as defined above), and a group of 3 to 6 membered ring containing 1 to 2 oxygen atoms. That is at least one selected from the group;
Substituent B1 is
At least one selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, and a C3-C8 cycloalkoxy group;
Substituent C is
Hydroxyl group, cyano group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C8 cycloalkoxy group, R31R32N- (wherein R31 and R32 are the same as R21 And R22), and R30-L3- (wherein R30 has the same meaning as R14 and L3 has the same meaning as L1), and at least one selected from the group consisting of Seeds;
Substituent D is
At least one selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group;
Substituent D1 is
Hydroxyl group, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C8 cycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, and C3-C8 cycloalkoxy group Is at least one selected from the group consisting of ] The wood preservative which contains the compound or its salt represented by this as an active ingredient.
R1 is a cyano group,
A C1-C6 alkyl group optionally substituted with substituent A,
A C1-C6 haloalkyl group,
A C3-C8 cycloalkyl group optionally substituted with the substituent A,
A C2-C6 alkenyl group optionally substituted with the substituent A,
A C2-C6 haloalkenyl group,
A C2-C6 alkynyl group optionally substituted with substituent A,
Or R10R11N— (wherein R10 and R11 are each independently a hydrogen atom or a C1-C6 alkyl group);
R2 is a halogen atom,
Hydroxyl group,
A cyano group,
A C1-C6 alkyl group optionally substituted with the substituent B,
A C1-C6 haloalkyl group,
A C1-C6 alkoxy group optionally substituted with the substituent B,
A C1-C6 haloalkoxy group,
A C3-C8 cycloalkoxy group optionally substituted with the substituent B,
A C2-C6 alkenyloxy group optionally substituted with the substituent B,
A C3-C6 alkynyloxy group optionally substituted with the substituent B,
R20C (═O) O— (wherein R20 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group) , C3-C8 cycloalkoxy group, or R21R22N- (wherein R21 and R22 are each independently a hydrogen atom, a C1-C6 alkyl group optionally substituted with a substituent B1, C1-C6 Or a cycloalkyl group of C3 to C8, or R21 and R22 together with the nitrogen atom to which they are bonded, an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group, or an azocanyl group ),
Or R23-L2- (wherein, R23 represents an alkyl group or a C1 ~ C6 haloalkyl group, a C1 ~ C6, L2 is S, SO, or an SO 2.) Represents;
R3 is a hydrogen atom,
Halogen atoms,
A C1-C6 alkyl group optionally substituted with substituent C,
A C3-C8 cycloalkyl group optionally substituted with substituent C,
A C1-C6 alkoxy group that may be optionally substituted with a substituent C;
A C2-C6 alkynyl group optionally substituted with substituent C,
Or R30-L3- (wherein R30 has the same meaning as R23 above, and L3 has the same meaning as L2 above);
Y represents a phenyl group or a pyridyl group;
In the phenyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 4 appropriately,
In the pyridyl group, the substituent D is substituted at the ortho position, and the substituent D1 is independently independently substituted with 0 to 3 appropriately.
A wood preservative containing the compound according to claim 1 or a salt thereof as an active ingredient.
R1 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group optionally substituted with the substituent A;
R2 represents a halogen atom, a C1-C6 alkyl group optionally substituted with the substituent B, or a C1-C6 alkoxy group optionally substituted with the substituent B;
R3 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally substituted with a substituent C.
A wood preservative containing the compound according to claim 2 or a salt thereof as an active ingredient.
A wood preservation method comprising treating the wood preservative according to claim 1 into a woody material.
Use of the compound according to claim 1 as a wood preservative.