WO2015119099A1

WO2015119099A1 - Pyridine compound and application therefor

Info

Publication number: WO2015119099A1
Application number: PCT/JP2015/052938
Authority: WO
Inventors: 岩田　淳; 藤井　聡; 陽平宗井; 朝巳小林; 伸哉幸堀; 元亮佐藤; 英樹加藤; 博生井上; 陽子大沢; 茂樹西野
Original assignee: 日本曹達株式会社
Priority date: 2014-02-05
Filing date: 2015-02-03
Publication date: 2015-08-13
Also published as: JPWO2015119099A1; JP6221189B2

Abstract

The present invention obtains a compound indicated by formula (I) or a salt thereof. The present invention also obtains an agricultural and horticultural fungicide, a pest control agent, or a pesticide or miticide, that contains as the effective component thereof at least one selected from a group comprising said compound and a salt thereof. In the formula (I), R¹ indicates a hydrogen atom, R² and R³ each independently indicate an alkyl group, etc., R⁴ indicates a hydrogen atom, etc., and Q indicates one of the organic groups indicated by formulas (II-IV). In the formulas (II-IV), Ar¹ and Ar² indicate an aryl group, etc., R^a indicates a hydrogen atom, etc., A indicates an alkylene group, etc., B^a indicates an alkylene group, etc., T¹ indicates an unsubstituted or a G2-substituted arylalkoxyimino-alkyl group, and * indicates the bonding position for the organic group indicated by the formulas (II-IV).

Description

Pyridine compounds and uses thereof

The present invention relates to pyridine compounds and uses such as agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides. This application is Japanese Patent Application No. 2014-020833 filed in Japan on February 5, 2014. Claim the priority based on, the contents of which are incorporated herein.

In the cultivation of agricultural and horticultural crops, many control agents are used against crop diseases, but their use is limited and their use is limited by the emergence of drug-resistant pathogens. In many cases, it is difficult to say that it is a sufficiently satisfactory control agent because it causes phytotoxicity and pollution to the plant body, or is highly toxic to human and livestock and has a great impact on the environment. Therefore, there is a strong demand for the emergence of drugs that can be safely used with few such drawbacks.

Incidentally, Patent Document 1 discloses a pyridine compound represented by the formula (A) or the formula (B). According to Patent Document 1, this pyridine compound seems to be useful as a complex II inhibitor of an electron transport system.

WO2003 / 103667

An object of the present invention is to provide a novel pyridine compound, an agricultural and horticultural fungicide, a pest control agent, and an insecticide or acaricide.

As a result of studies to solve the above problems, the present invention including the following aspects has been completed.
[1] A compound represented by the formula (I) or a salt thereof.

In formula (I),
R ¹ represents a hydrogen atom, an unsubstituted or C 1-6 alkyl group substituted with G ¹ , or a halogeno group.
R ² and R ³ are each independently an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 3-8 cycloalkyl group, an unsubstituted or G ² A C6-10 aryl group substituted with or a halogeno group.
R ⁴ is a hydrogen atom, an unsubstituted or C1 ~ 6 alkyl group substituted with G ^1, unsubstituted or C2 ~ 6 alkenyl group substituted with G ^1, which is substituted by unsubstituted or G ¹ C2 substituted 1-6 alkynyl group, an unsubstituted or C3 ~ 8 cycloalkyl group substituted with G ^1, unsubstituted or C6 ~ 10 aryl C1 to 6 alkyl group substituted with G ^2, unsubstituted or with G ² 3- to 10-membered heterocyclyl group C1-6 alkyl group, formyl group, C1-6 alkylcarbonyl group which is unsubstituted or substituted with G ¹ , C6-10 arylcarbonyl group which is unsubstituted or substituted with G ² , unsubstituted or C1 ~ 6 alkoxycarbonyl group substituted with G ^1, unsubstituted or C2 ~ 6 alkenyloxycarbonyl group substituted with G ^1, unsubstituted or G ^A C1-6 alkylsulfonyl group substituted with ¹ , a C1-6 alkylaminocarbonyl group unsubstituted or substituted with G ¹ , a (C1-6 alkylthio) carbonyl group unsubstituted or substituted with G ¹ , or A C1-6 alkylamino (thiocarbonyl) group which is unsubstituted or substituted with G ¹ or a group represented by the formula (V) is shown.

In formula (V),
G ^a independently represents a hydrogen atom, an unsubstituted or C1 ~ 6 alkyl group substituted with G ^1, unsubstituted or C2 ~ 6 alkenyl group substituted with G ^1, unsubstituted or with G ¹ substituted C2 ~ 6 alkynyl group, a unsubstituted or C3 ~ 8 cycloalkyl group substituted by G ¹ or unsubstituted or C6 ~ 10 aryl group substituted by G ^2,.
G ^b represents a hydrogen atom, an unsubstituted or C1 ~ 6 alkyl group substituted with G ^1, unsubstituted or C2 ~ 6 alkenyl group substituted with G ^1, which is substituted by unsubstituted or G ¹ C2 2-6 alkynyl group, an unsubstituted or C3 ~ 8 cycloalkyl group substituted with G ^1, unsubstituted or C6 ~ 10 aryl group substituted by G ² 3 or substituted with unsubstituted or G ^2, Represents a 10-membered heterocyclyl group;
T is an oxygen atom, oxycarbonyl group, carbonyloxy group, oxycarbonyloxy group, sulfur atom, (thio) carbonyl group, carbonyl (thio) group, (thio) carbonyloxy group, oxycarbonyl (thio) group, or- A divalent group represented by O—C (═O) —N (G ^b ) — is shown.
* Indicates the bonding position of the group represented by the formula (V).

G ¹ is a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, a C1-6 alkoxycarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy A group, a cyano group, or a halogeno group.
G ² is a C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkyl group, tri C1-6 alkyl Silyl C1-6 alkyl group, Tri C1-6 alkylsilyl C2-6 alkynyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group , C1-6 haloalkoxy group, C2-6 alkenyloxy group, C2-6 alkynyloxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyloxy group C1-6 alkoxycarbonyloxy group, C1-6 alkoxycarbonylamino group, The or C6 ~ 10 aryl group substituted by G ^21, unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkyl group substituted with G ^21, unsubstituted or C6 ~ 10 aryloxy group which is substituted by G ²¹ , unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxy group substituted by G ^21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^21, 3 substituted with unsubstituted or G ²¹ ~ 10-membered heterocyclyl C1-6 alkyl group, 3-10 membered heterocyclyloxy group, unsubstituted or substituted with G ²¹ , C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 Haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, cyano group, nitro group, halogeno group , C1-6 alkylene group, C1-6 alkylenedioxy group, or C1-6 haloalkylenedioxy group.
G ²¹ represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a cyano group, a nitro group, or a halogeno group.
Q represents any one of the organic groups represented by the formulas (II) to (IV).

In formulas (II) to (IV),
Ar ¹ represents an unsubstituted or C6 ~ 10 aryl group substituted by G ² or unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^2,.
Ar ² is unsubstituted or C6 ~ 10 aryl group substituted by G ^2, unsubstituted or C6 ~ 10 aryloxy group which is substituted by G ^2, C6 ~ 10 substituted with unsubstituted or G ² aryl C1 ~ 6 alkoxy group, an unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^2, unsubstituted or 3-10 membered heterocyclyloxy group substituted with G ² or unsubstituted or G ^2, A substituted 3- to 10-membered heterocyclylthio group is shown.
R ^a represents a hydrogen atom, an amino group, an unsubstituted or substituted C 1-6 alkyl group with G ¹ , or an unsubstituted or substituted C 2-10 aryl group with G ² .
A is unsubstituted or C1 ~ C6 alkylene group substituted with G ^3, unsubstituted or C2 ~ C6 alkenylene group substituted with G ^3, unsubstituted or C2 ~ C6 alkynylene group substituted with G ³ shows the unsubstituted or C1 ~ C6 alkylene group which is substituted by G ^3, unsubstituted or is oxy C1 ~ C6 alkylene group substituted with G ^3, unsubstituted C3 ~ C6 cycloalkylene group or a carbonyl group, .
Here, G ³ is a C1-6 alkyl group, a C1-6 alkoxy group, a formyl group, a C1-6 alkylcarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a halogeno group, a C1-6 alkylene group, Or represents an oxo group.
B ^a is unsubstituted or C1 ~ C6 alkylene group substituted with G ^4, unsubstituted or C2 ~ C6 alkenylene group substituted with G ^4, unsubstituted or C2 ~ C6 alkynylene substituted with G ⁴ group, an unsubstituted or C3 ~ C6 cycloalkylene group substituted by G ^4, unsubstituted or C4 ~ C6 cycloalkenylene group substituted with G ⁴ 3 ~ 6 or of unsubstituted or substituted by G ^4, The group represented by a membered heterocyclylene group is shown.
Here, G ⁴ is a C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1— 6 alkoxy group, C1 ~ 6 haloalkoxy group, C2 ~ 6 alkenyloxy group, an unsubstituted or C6 ~ 10 aryl group substituted by G ^21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ²¹ , a cyano group, a halogeno group, C1 ~ 6 alkylene group, C1 ~ 6 alkylenedioxy group, an oxo group, C3 ~ 8 cycloalkyl C1 ~ 6 alkyl group, unsubstituted or substituted with G ²¹ C6 ~ 10 aryl C1 1-6 alkyl group, an unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxy group substituted by G ^21, 3 substituted with unsubstituted or G ²¹ - 0-membered heterocyclyl C1 ~ 6 alkyl group, substituted with C3 ~ 8 cycloalkyloxy C1 ~ 6 alkyl group, unsubstituted or C6 ~ 10 aryloxy C1 ~ 6 alkyl group substituted with G ^21, unsubstituted or G ²¹ is 3- to 10-membered heterocyclyloxy C1 ~ 6 alkyl group, C1 ~ 6 alkoxyimino group, an unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxyimino group substituted by G ²¹ or C1 ~ 6 alkyl hydrazino group, Indicates.
In addition, ^a part of the substituent G ⁴ on Ba may bond to a carbon atom on Ar ² to form a 5- to 6-membered ring.
T ¹ represents (unsubstituted or G ² -substituted C 6-10 aryl C 1-6 alkoxyimino) -C 1-6 alkyl group or ferrocenyl-C 1-6 alkyl group.
* Indicates the bonding position of the organic group represented by formula (II) to formula (IV).

[2] An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the group consisting of the compound according to [1] and a salt thereof.
[3] A pest control agent containing at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient.
[4] An insecticide or acaricide containing at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient.

The pyridine compound according to the present invention is a novel compound that has effects such as pest control, bactericidal, acaricidal, insecticidal, etc., does not cause phytotoxicity to plants, and has little toxicity to human fish and environmental impact. . In particular, it exhibits an excellent control effect against wheat diseases. The pyridine compound according to the present invention is useful as an active ingredient of agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.

The pyridine compound according to the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) and a salt thereof.

[R ¹ ]
R ¹ represents a hydrogen atom, an unsubstituted or C 1-6 alkyl group substituted with G ¹ , or a halogeno group.
The C1-6 alkyl group may be linear or branched if it has 3 or more carbon atoms. Examples of the C1-6 alkyl group include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n -Hexyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.
Examples of the halogeno group include a fluoro group, a chloro group, a bromo group, and an iodo group.

The substituent G ¹ is a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, a C1-6 alkoxycarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group. , A cyano group, or a halogeno group.

C1-6 alkoxy groups include methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, i-propoxy, i-butoxy, s-butoxy , T-butoxy group, i-hexyloxy group and the like.
Examples of the C1-6 alkoxy group include a methoxymethoxy group and a methoxyethoxy group.
Examples of the C1-6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
Examples of the C1-6 alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, and a butyryloxy group.
Examples of the C1-6 alkoxycarbonyloxy group include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, and a t-butoxycarbonyloxy group. be able to.
The halogeno group in the substituent G ¹ is as described above.

In the present invention, R ¹ is preferably an unsubstituted or substituted C 1-6 alkyl group substituted with G ¹ , or a halogeno group, more preferably an unsubstituted C 1-6 alkyl group or halogeno group.

[R ² and R ³ ]
R ² and R ³ are each independently an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 3-8 cycloalkyl group, an unsubstituted or G ² A C6-10 aryl group substituted with or a halogeno group.
The C1-6 alkyl group, halogeno group, and substituent G ¹ in R ² and R ³ are as described above.
Examples of the C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a 2-adamantyl group.
Examples of the C6-10 aryl group include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group.

Substituent G ² is a C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkyl group, tri C1-6 6 alkylsilyl C1-6 alkyl group, tri C1-6 alkylsilyl C2-6 alkynyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 Alkoxy group, C1-6 haloalkoxy group, C2-6 alkenyloxy group, C2-6 alkynyloxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyl Oxy group, C1-6 alkoxycarbonyloxy group, C1-6 alkoxycarbonylamino group Unsubstituted or C6 ~ 10 aryl group substituted by G ^21, unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkyl group substituted with G ^21, unsubstituted or C6 ~ 10 aryl which is substituted by G ²¹ oxy group, an unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxy group substituted by G ^21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^21, which is substituted by unsubstituted or G ²¹ 3- to 10-membered heterocyclyl C1-6 alkyl group, unsubstituted or G ^21- substituted 3- to 10-membered heterocyclyloxy group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1 -6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, cyano group, nitro group, halo A geno group, a C1-6 alkylene group, a C1-6 alkylenedioxy group, or a C1-6 haloalkylenedioxy group;

In the substituent G ² , C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1-6 alkylcarbonyloxy group, C1-6 alkoxycarbonyl group, The C1-6 alkoxycarbonyloxy group, C6-10 aryl group, and halogeno group are as described above.

C2-6 alkenyl groups include vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, -Methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
Examples of the C2-6 alkynyl group include ethynyl group, 1-propynyl group (propargyl group), 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group 1,1-dimethyl-2-butynyl group and the like.

The C1-6 alkoxy C1-6 alkyl group is the above-described C1-6 alkoxy group substituted for the C1-6 alkyl group already described. C1-6 alkoxy C1-6 alkyl group includes methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i -Propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group and the like can be mentioned.

The tri C1-6 alkylsilyl group is a C1-6 alkyl group in which a triC1-6 alkylsilyl group is substituted for the C1-6 alkyl group already described. Examples of the tri C1-6 alkylsilyl C1-6 alkyl group include 2- (trimethylsilyl) ethyl group.
The tri C1-6 alkylsilyl C2-6 alkynyl group is obtained by substituting the C2-6 alkynyl group already described with a tri C1-6 alkylsilyl group. Examples of the tri-C1-6 alkylsilyl C1-6 alkynyl group include 2- (trimethylsilyl) ethynyl group.

The C2-6 alkenyloxy group is a hydroxyl group substituted with a C2-6 alkenyl group. Examples of the C2-6 alkenyloxy group include a vinyloxy group, a 1-propenyloxy group, and a 2-propenyloxy group (allyloxy group).
The C2-6 alkynyloxy group is a hydroxyl group substituted with a C2-6 alkynyl group. Examples of the C2-6 alkynyloxy group include an ethynyloxy group and a 1-propynyloxy group (propargyloxy group).

The C1-6 alkylcarbonyl group is a group in which the above C1-6 alkyl group is bonded to a carbonyl group. Examples of the C1-6 alkylcarbonyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, and a pivaloyl group.

The C1-6 alkoxycarbonylamino group is a group in which the above-described C1-6 alkoxycarbonyl group is substituted on the amino group. Examples of the C1-6 alkoxycarbonylamino group include a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, an i-propoxycarbonylamino group, an n-butoxycarbonylamino group, and a t-butoxycarbonylamino group. be able to.

The C6-10 aryl C1-6 alkyl group is a C1-6 alkyl group substituted with a C6-10 aryl group. Examples of the C6-10 aryl C1-6 alkyl group include a benzyl group and a phenethyl group.
The C6-10 aryloxy group is a group in which the above-described C6-10 aryl group is substituted on the hydroxyl group. Examples of the C6-10 aryloxy group include a phenoxy group and a naphthoxy group.
The C6-10 aryl C1-6 alkoxy group is a group in which the above-described C6-10 aryl C1-6 alkyl group is substituted on the hydroxyl group. Examples of the C6-10 aryl C1-6 alkoxy group include a benzyloxy group and a phenethyloxy group.

The 3- to 10-membered heterocyclyl group is a cyclic group containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is heterocyclyl, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the 3- to 10-membered heterocyclyl group include a 3- to 10-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.

As a 3 to 10-membered saturated heterocyclyl group,
A 3-membered saturated heterocyclyl group such as an aziridinyl group or an oxiranyl group;
A 4-membered saturated heterocyclyl group such as an azetidinyl group or an oxetanyl group;
5-membered saturated heterocyclyl group such as pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, imidazolidinyl group, pyrazolidinyl group, dioxolanyl group;
6-membered saturated heterocyclyl groups such as piperidyl group, piperazinyl group, morpholinyl group, tetrahydropyranyl group, dioxolanyl group, dioxanyl group;
Etc.

As a 5- to 10-membered heteroaryl group,
5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl;
6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridanidyl group, triazinyl group;
9-membered heteroaryl groups such as indolyl group, isoindolyl group, benzofuranyl group, indazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, benzisothiazolyl group;
10-membered heteroaryl groups such as quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxanyl group;
Etc.

As a 5-6 membered partially unsaturated heterocyclyl group,
5-membered partially unsaturated heterocyclyl group such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group;
6-membered partially unsaturated heterocyclyl group such as isoxazolinyl group and dihydropyranyl group;
Etc.

The 3- to 10-membered heterocyclyl group for G ² is preferably a 5- to 6-membered saturated heterocyclyl group or a 5- to 6-membered heteroaryl group.

The 3- to 10-membered heterocyclyl C1-6 alkyl group is a C1-6 alkyl group substituted with a 3- to 10-membered heterocyclyl group. The 3- to 10-membered heterocyclyl C1-6 alkyl group is preferably a 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as tetrahydrofuranylmethyl group, tetrahydropyranylmethyl group, dioxolanylmethyl group, dioxanylmethyl group, etc. Groups; 5- to 6-membered heteroaryl C1-6 alkyl groups such as a pyrazolylmethyl group and a pyridylmethyl group.
The 3- to 10-membered heterocyclyloxy group is a hydroxyl group substituted with a 3- to 10-membered heterocyclyl group. Examples of the 3- to 10-membered heterocyclyloxy group include a pyrazolyloxy group and a pyridyloxy group. The 3- to 10-membered heterocyclyloxy group is preferably a 5- to 6-membered saturated heterocyclyloxy group or a 5- to 6-membered heteroaryloxy group.
The C1-6 alkylthio group is obtained by substituting a C1-6 alkyl group for an SH group. Examples of the C1-6 alkylthio group include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, i-butylthio group and the like.
The C1-6 alkylsulfinyl group is a C1-6 alkyl group bonded to a sulfinyl group. Examples of the C1-6 alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.
The C1-6 alkylsulfonyl group is a sulfonyl group having a C1-6 alkyl group bonded thereto. Examples of the C1-6 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

The C1-6 alkylene group is a divalent group formed by removing two hydrogen atoms from the C1-6 alkane. Examples of the C1-6 alkylene group include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, and a propane-1,2-diyl group (that is, a propylene group).
The C1-6 alkylenedioxy group is a divalent group formed by replacing two hydrogen atoms in a C1-6 alkane with an oxy group. Examples of the C1-6 alkylenedioxy group include a methylenedioxy group (—OCH ₂ O—), an ethylenedioxy group (—OCH ₂ CH ₂ O—), and a trimethylenedioxy group. Examples of the C6-10 aryl group substituted with a C1-6 alkylenedioxy group as G ² include a 2,3-dihydro-benzo [1,4] dioxyl group, a benzo [1,3] dioxolyl group, and the like. Can do.

C1-6 haloalkyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, C1-6 haloalkoxy group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, and C1 The -6 haloalkylenedioxy group includes the already described C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C1-6 alkoxy group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, A halogeno group is substituted on the C1-6 alkylsulfonyl group and the C1-6 alkylenedioxy group.
C1-6 haloalkyl groups include fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2, Examples include 2,2-trifluoro-1-trifluoromethylethyl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group and the like.

Examples of the C2-6 haloalkenyl group include a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group.
Examples of the C2-6 haloalkynyl group include a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group.
C1-6 haloalkoxy groups include chloromethoxy, dichloromethoxy, difluoromethoxy, trichloromethoxy, trifluoromethoxy, 1-fluoroethoxy, 1,1-difluoroethoxy, 2,2,2- Examples thereof include a trifluoroethoxy group, a pentafluoroethoxy group, and a 2,2,3,4,4,4-hexafluoro-butoxy group.
C1-6 haloalkylthio group, trifluoromethylthio group, 2,2,2-trifluoroethylthio group and the like can be mentioned.
Examples of the C1-6 haloalkylsulfinyl group include a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.
Examples of the C1-6 haloalkylsulfonyl group include a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.
Examples of the C1-6 haloalkylenedioxy group include a difluoromethylenedioxy group (—OCF ₂ O—) and a tetrafluoroethylenedioxy group (—OCF ₂ CF ₂ O—). Examples of the C6-10 aryl group substituted by the C1-6 haloalkylenedioxy group as G ² include a 2,2,3,3-tetrafluoro-2,3-dihydro-benzo [1,4] dioxyl group, A 2,2-difluoro-benzo [1,3] dioxolyl group and the like can be mentioned.

The substituent G ²¹ represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a cyano group, a nitro group, or a halogeno group. These are as already described.

All have in the present invention, the R ^2, preferably C1 ~ 6 alkyl group substituted with unsubstituted or G ^1, unsubstituted C1 ~ 6 alkyl group is more preferable.
In the present invention, R ³ is an unsubstituted or C 1-6 alkyl group substituted with G ¹ (preferably a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, or a halogeno group). An unsubstituted C3-8 cycloalkyl group (preferably a C3-4 cycloalkyl group), an unsubstituted C6-10 aryl group (preferably a phenyl group), or a halogeno group, preferably unsubstituted or substituted with G ¹ More preferred is a C1-6 alkyl group or a halogeno group.

[R ⁴ ]
R ⁴ is a hydrogen atom, an unsubstituted or C1 ~ 6 alkyl group substituted with G ^1, unsubstituted or C2 ~ 6 alkenyl group substituted with G ^1, which is substituted by unsubstituted or G ¹ C2 substituted 1-6 alkynyl group, an unsubstituted or C3 ~ 8 cycloalkyl group substituted with G ^1, unsubstituted or C6 ~ 10 aryl C1 to 6 alkyl group substituted with G ^2, unsubstituted or with G ² 3 to 10-membered heterocyclyl C1-6 alkyl group, formyl group, C1-6 alkylcarbonyl group which is unsubstituted or substituted with G ¹ , C6-10 arylcarbonyl group which is unsubstituted or substituted with G ² , unsubstituted or C1 ~ 6 alkoxycarbonyl group substituted with G ^1, unsubstituted or C2 ~ 6 alkenyloxycarbonyl group substituted with G ^1, unsubstituted or G ¹ Substituted C1 ~ 6 alkylsulfonyl group, an unsubstituted or C1 ~ 6 alkylaminocarbonyl group substituted with G ^1, unsubstituted or substituted with G ¹ (C1 ~ 6 alkylthio) carbonyl group or unsubstituted, Or a C1-6 alkylamino (thiocarbonyl) group substituted with G ¹ or a group represented by the formula (V).

In R ⁴ , a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3-8 cycloalkyl group, a C1-6 alkylcarbonyl group, a C1-6 alkoxycarbonyl group, a C1-6 alkylsulfonyl group, The substituent G ¹ and the substituent G ² are as described above.

The C6-10 aryl C1-6 alkyl group is a C1-6 alkyl group substituted with a C6-10 aryl group. Examples of the C6-10 aryl C1-6 alkyl group include a benzyl group and a phenethyl group.
The 3- to 10-membered heterocyclyl C1-6 alkyl group is a C1-6 alkyl group substituted with a 3- to 10-membered heterocyclyl group. The 3- to 10-membered heterocyclyl C1-6 alkyl group is preferably a 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as tetrahydrofuranylmethyl group, tetrahydropyranylmethyl group, dioxolanylmethyl group, dioxanylmethyl group, etc. Groups; 5- to 6-membered heteroaryl C1-6 alkyl groups such as a pyrazolylmethyl group and a pyridylmethyl group.
The C6-10 arylcarbonyl group is a group in which a C6-10 aryl group is bonded to a carbonyl group. Examples of the C6-10 arylcarbonyl group include a benzoyl group.

Examples of the C2-6 alkenyloxycarbonyl group include a vinyloxycarbonyl group, a 1-propenyloxycarbonyl group, and a 2-propenyloxycarbonyl group (allyloxycarbonyl group).
Examples of the C1-6 alkylaminocarbonyl group include a methylaminocarbonyl group and a dimethylaminocarbonyl group.
Examples of the (C1-6 alkylthio) carbonyl group include (methylthio) carbonyl group and (ethylthio) carbonyl group.
Examples of the C1-6 alkylamino (thiocarbonyl) group include a methylamino (thiocarbonyl) group and a dimethylamino (thiocarbonyl) group.

C 1-6 alkyl group, C 2-6 alkenyl group, C 2-6 alkynyl group, C 3-8 cycloalkyl group, C 6-10 aryl group, 3-10 membered heterocyclyl group in G ^a and G ^b in formula (V) , Substituent G ¹ , and substituent G ² are as described above.
The 3- to 10-membered heterocyclyl group for G ^b is preferably a 5- to 6-membered saturated heterocyclyl group or a 5- to 6-membered heteroaryl group.

Examples of the group represented by the formula (V) include the following.

In the present invention, R ⁴ represents a hydrogen atom, a C 1-6 alkyl group which is unsubstituted or substituted with G ¹ (preferably a C 1-6 alkoxycarbonyl group, C 1-6 alkoxycarbonyloxy group), A C2-6 alkenyl group substituted or substituted with G ¹ , an unsubstituted or C6-10 aryl C1-6 substituted with G ² (preferably a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group) alkyl group, an unsubstituted or C1 ~ 6 alkyl group substituted with G ¹ (more preferably unsubstituted), unsubstituted or G ¹ (preferably C1 ~ 6 alkoxy group, a halogeno group) substituted with C1 -6 alkoxycarbonyl group, C2-6 alkenyloxycarbonyl group unsubstituted or substituted with G ¹ (more preferably unsubstituted), unsubstituted Or a C1-6 alkylsulfonyl group substituted by G ¹ (more preferably unsubstituted), an unsubstituted or C1-6 alkylaminocarbonyl group substituted by G ¹ (more preferably unsubstituted), unsubstituted Or a (C1-6 alkylthio) carbonyl group substituted with G ¹ (more preferably unsubstituted), or a C1-6 alkylamino (thiocarbonyl) group unsubstituted or substituted with G ¹ (more preferably unsubstituted) ) is preferably a hydrogen atom, an unsubstituted or C1 ~ 6 alkyl group substituted by G ¹ or unsubstituted or C1 ~ 6 alkoxycarbonyl group substituted with G ^1, is more preferable.

[Q]
Q represents any one of the organic groups represented by the formulas (II) to (IV). Note that * indicates the bonding position of the organic group represented by the formulas (II) to (IV).

<R ^a >
R ^a is a hydrogen atom, an amino group, a C1-6 alkyl group which is unsubstituted or substituted with G ¹ , or a C6-10 aryl which is unsubstituted or substituted with G ² (preferably a C1-6 haloalkyl group) Indicates a group. The C1-6 alkyl group, the C6-10 aryl group, the substituent G ¹ and the substituent G ² in R ^a are as described above.
Among these, R ^a is preferably ^a hydrogen atom or an unsubstituted or C 1-6 alkyl group substituted with G ¹ .
Further, the C1-6 alkyl group in R ^a is preferably unsubstituted.

<A>
A is unsubstituted or C1 ~ C6 alkylene group substituted with G ^3, unsubstituted or C2 ~ C6 alkenylene group substituted with G ^3, unsubstituted or C2 ~ C6 alkynylene group substituted with G ³ shows the unsubstituted or C1 ~ C6 alkylene group which is substituted by G ^3, unsubstituted or is oxy C1 ~ C6 alkylene group substituted with G ^3, unsubstituted C3 ~ C6 cycloalkylene group or a carbonyl group, . The C1-C6 alkylene group for A is as described above.

The C2-C6 alkenylene group is a divalent group formed by removing two hydrogen atoms from the C2-C6 alkene. Examples of the C2 to C6 alkenylene group include an ethenylene group, a propenylene group, and a butenylene group.
The C2-C6 alkynylene group is a divalent group formed by removing two hydrogen atoms from the C2-C6 alkyne. Examples of the C2 to C6 alkynylene group include an ethynylene group, a propynylene group, a butynylene group, and the like.
Examples of the C1-C6 alkyleneoxy group include a methyleneoxy group (—CH ₂ O—) and an ethyleneoxy group (—CH ₂ CH ₂ O—).
Examples of the oxy C1-C6 alkylene group include an oxymethylene group (—OCH ₂ —) and an oxyethylene group (—OCH ₂ CH ₂ —).

The C3-C6 cycloalkylene group is a divalent group formed by removing two hydrogen atoms from a C3-C6 cycloalkane. The C3-C6 cycloalkylene group includes a cyclopropylene group (1,2-cyclopropylene group), a cyclobutylene group (1,2-cyclobutylene group, or 1,3-cyclobutylene group), a cyclopentylene group (1 , 2-cyclopentylene group, or 1,3-cyclopentylene group), cyclohexylene group (1,2-cyclohexylene group, 1,3-cyclohexylene group, or 1,4-cyclohexylene group), etc. Preferably, it is a cyclopropylene group.

G ³ is a C1-6 alkyl group, C1-6 alkoxy group, formyl group, C1-6 alkylcarbonyl group, formyloxy group, C1-6 alkylcarbonyloxy group, halogeno group, C1-6 alkylene group, or oxo group Indicates. In G ³ , the C1-6 alkyl group, C1-6 alkoxy group, C1-6 alkylcarbonyl group, C1-6 alkylcarbonyloxy group, halogeno group, and C1-6 alkylene group are as described above.

Among these, A is been C1 ~ C6 alkylene group (more preferably an unsubstituted) substituted with unsubstituted or G ^3, unsubstituted or C2 ~ C6 alkenylene group substituted with G ³ (more preferably nothingness Substituted), unsubstituted or substituted C1-C6 alkyleneoxy groups with G ³ (more preferably unsubstituted), or unsubstituted C3-C6 cycloalkylene groups (more preferably unsubstituted). Alternatively, it is more preferably a C1-C6 alkylene group (more preferably unsubstituted) substituted with G ³ .

<Ar ¹ >
Ar ¹ represents an unsubstituted or C6 ~ 10 aryl group substituted by G ² or unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^2,. The C6-10 aryl group, 3- to 10-membered heterocyclyl group, and substituent G ² in Ar ¹ are as described above.
Preferred examples of the 3- to 10-membered heterocyclyl group for Ar ¹ include 5- to 10-membered heteroaryl groups such as a pyrazolyl group, a pyridyl group, a pyrimidinyl group, and a quinolinyl group.
Among them, Ar ¹ is preferably an unsubstituted or C6 ~ 10 aryl group substituted by G ² or unsubstituted or 5-6 membered heteroaryl group substituted with G ^2, unsubstituted or more preferably a pyridyl group substituted with phenyl group or an unsubstituted or G ² substituted with G ^2.
G ² in Ar ¹ is more preferably a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, a C6-10 aryl group (preferably a phenyl group), and / or a halogeno group.

<Ar ² >
Ar ² is unsubstituted or C6 ~ 10 aryl group substituted by G ^2, unsubstituted or C6 ~ 10 aryloxy group which is substituted by G ^2, C6 ~ 10 substituted with unsubstituted or G ² aryl C1 ~ 6 alkoxy group, an unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^2, unsubstituted or 3-10 membered heterocyclyloxy group substituted with G ² or unsubstituted or G ^2, A substituted 3- to 10-membered heterocyclylthio group is shown.

The C6-10 aryl group in Ar ² is as described above, and is preferably a phenyl group.
The C6-10 aryloxy group in Ar ² is as described above, and is preferably a phenoxy group.
The 3- to 10-membered heterocyclyl group in Ar ² is as described above, preferably a 5- to 6-membered heteroaryl group, more preferably a thienyl group, a pyrazolyl group, a pyridyl group, or a pyrazinyl group. .
The 3- to 10-membered heterocyclyloxy group in Ar ² is as described above, preferably a 5- to 6-membered heteroaryloxy group, more preferably a pyrazolyloxy group, a pyridyloxy group, a pyrazinyloxy group, a pyrimidinyloxy group. More preferably a pyridyloxy group, a pyrazinyloxy group, or a pyrimidinyloxy group.
The C6-10 aryl C1-6 alkoxy group in Ar ² is as described above, and is preferably a phenyl C1-6 alkoxy group.

The 3- to 10-membered heterocyclylthio group in Ar ² is obtained by substituting a 3- to 10-membered heterocyclyl group for the SH group. The 3- to 10-membered heterocyclylthio group is preferably a 5- to 6-membered heteroarylthio group such as a pyrazolylthio group or a pyridylthio group, and more preferably a pyridylthio group.

Substituent G ² is as described above, and preferably C 1-6 haloalkyl group, C 1-6 alkoxy group, C 1-6 alkoxy C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 2-6 alkynyl. group, tri C1 ~ 6 alkyl silyl C2 ~ 6 alkynyl, unsubstituted or C6 ~ 10 aryl group substituted by G ^21, unsubstituted or C6 ~ 10 aryloxy group which is substituted by G ^21, unsubstituted or 5 to 6-membered heterocyclyl group which is substituted by G ^21, unsubstituted or 5-6 membered heterocyclyloxy group which is substituted by G ^21, shows a halogeno group or a C1 ~ 6 alkylenedioxy group, more preferably, C1-6 haloalkyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1-6 haloalkoxy group, C2-6 a Kiniru group, tri C1 ~ 6 alkyl silyl ethynyl group, an unsubstituted or phenyl substituted with G ^21, unsubstituted or phenoxy group substituted with G ^21, unsubstituted or substituted pyrazolyl group G ²¹ Represents an unsubstituted or G ²¹ -substituted pyridyloxy group, a halogeno group, or a C1-2 alkylenedioxy group.
The substituent G ²¹ is as described above, and preferably represents a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group.

Among them, Ar ² is preferably unsubstituted or C6 ~ 10 aryl group substituted by G ^2, unsubstituted or C6 ~ 10 aryloxy group which is substituted by G ^2, unsubstituted or G ² (preferably halogeno group) C6 ~ 10 aryl C1 ~ 6 alkoxy group substituted by, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^2, 3-10 substituted with unsubstituted or G ² A membered heterocyclyloxy group, or a 3 to 10 membered heterocyclylthio group (preferably a 5 to 6 membered heteroarylthio group) which is unsubstituted or substituted with G ² (preferably a halogeno group and / or a C1-6 haloalkyl group) , More preferably a pyridylthio group).

<B ^a >
B ^a is unsubstituted or C1 ~ C6 alkylene group substituted with G ^4, unsubstituted or C2 ~ C6 alkenylene group substituted with G ^4, unsubstituted or C2 ~ C6 alkynylene substituted with G ⁴ group, an unsubstituted or C3 ~ C6 cycloalkylene group substituted by G ^4, unsubstituted or C4 ~ C6 cycloalkenylene group substituted with G ⁴ 3 ~ 6 or of unsubstituted or substituted by G ^4, The group represented by a membered heterocyclylene group is shown.
In B ^a, C1 ~ C6 alkylene group, C2 ~ C6 alkenylene group, and C2 ~ C6 alkynylene radicals are those as already mentioned.

The C3-C6 cycloalkylene group is a divalent group formed by removing two hydrogen atoms from a C3-C6 cycloalkane. The C3-C6 cycloalkylene group includes a cyclopropylene group (1,2-cyclopropylene group), a cyclobutylene group (1,2-cyclobutylene group, or 1,3-cyclobutylene group), a cyclopentylene group (1 , 2-cyclopentylene group, or 1,3-cyclopentylene group), cyclohexylene group (1,2-cyclohexylene group, 1,3-cyclohexylene group, or 1,4-cyclohexylene group), etc. Preferably, it is a cyclopentylene group or a cyclohexylene group.

The C4-C6 cycloalkenylene group is a divalent group formed by removing two hydrogen atoms from a C3-C6 cycloalkene. The C4 to C6 cycloalkenylene group includes a cyclobutenylene group (1,2-cyclobutenylene group, 1,3-cyclobutenylene group, 1,3-cyclobutenylene group, or 3,4-cyclobutenylene group), cyclopentenylene group (1, 2-cyclopentenylene group, 1,3-cyclopentenylene group, 1,4-cyclopentenylene group or 1,5-cyclopentenylene group), cyclohexenylene group (1,2-cyclohexenylene group) A selenylene group, a 1,3-cyclohexenylene group, a 1,4-cyclohexenylene group, and the like. Among these, a cyclopentenylene group or a cyclohexenylene group is preferable.

A 3- to 6-membered heterocyclylene group is a divalent group formed by removing two hydrogen atoms from a heteroalicyclic compound. The heteroalicyclic compound is a non-aromatic compound containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as constituent atoms of the ring.
Examples of the 3- to 6-membered heterocyclylene group include a 3- to 6-membered saturated heterocyclylene group or a 5- to 6-membered partially unsaturated heterocyclylene group.
Examples of the 3- to 6-membered heterocyclylene group include dioxolanylene group, dihydrofuranylene group, tetrahydrofuranylene group, pyrrolylene group, pyrrolidinylene group, pyrazolylene group, pyrazolidinylene group, imidazolylene group, imidazolidinylene group, oxazolidylene group, oxazolidinylene group Group, thiazolinylene group, thiazolidinylene group, isoxazolidinylene group, isothiazolidinylene group, dihydropyranylene group, tetrahydropyranylene group, piperidinylene group, piperazinylene group, morpholinylene group and the like.
Among these, as the 3- to 6-membered heterocyclylene group, a 5- to 6-membered saturated heterocyclylene group is preferable, and a dioxolanylene group, a tetrahydrofuranylene group, and a piperidinylene group are more preferable.
In certain embodiments, the 3-6 membered heterocyclylene group (preferably a 5-6 membered saturated heterocyclylene group, more preferably a piperidinylene group) may be a C1-6 alkylene group and may be bridged.

Of these, B ^a is preferably unsubstituted or C1 ~ C6 alkylene group substituted with G ^4, unsubstituted or C2 ~ C6 alkenylene group substituted with G ^4, unsubstituted or with G ⁴ substituted C3 ~ C6 cycloalkylene group, a unsubstituted or C4 ~ C6 cycloalkenylene group substituted with G ⁴ or unsubstituted or 3-6 membered heterocyclylene group substituted by G ^4,, more preferably, unsubstituted or C1 ~ C6 alkylene group substituted by G ^4, or shows a unsubstituted or C3 ~ C6 cycloalkylene group substituted with G ^4.

G ⁴ is a C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group , C1 ~ 6 haloalkoxy group, C2 ~ 6 alkenyloxy group, an unsubstituted or C6 ~ 10 aryl group substituted by G ^21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^21, a cyano group , Halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C3-8 cycloalkyl C1-6 alkyl group, unsubstituted or substituted with G ²¹ C6-10 aryl C1-6 alkyl group, an unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxy group substituted by G ^21, 3 ~ 10 membered f substituted with unsubstituted or G ²¹ Roshikuriru C1 ~ 6 alkyl group, C3 ~ 8 cycloalkyloxy C1 ~ 6 alkyl group, unsubstituted or C6 ~ 10 aryloxy C1 ~ 6 alkyl group substituted with G ^21, which is substituted by unsubstituted or G ²¹ 3-10 membered heterocyclyloxy C1 ~ 6 alkyl group, a C1 ~ 6 alkoxyimino group, an unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxyimino group substituted by G ²¹ or C1 ~ 6 alkyl hydrazino group, . Among these, G ⁴ is C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1 1-6 haloalkoxy group, C2 ~ 6 alkenyloxy group, an unsubstituted or C6 ~ 10 aryl group substituted by G ^21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^21, unsubstituted or 3-10 membered heterocyclyl C1 ~ 6 alkyl group substituted with G ^21, C3 ~ 8 cycloalkyloxy C1 ~ 6 alkyl group, unsubstituted or C6 ~ 10 aryloxy C1 ~ 6 alkyl group substituted with G ^21, Or an unsubstituted or G ²¹ -substituted 3- to 10-membered heterocyclyloxy C 1-6 alkyl group.

In G ⁴ , C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, C1-6 haloalkyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1-6 alkylenedioxy group, C6-10 aryl group, C6-10 aryl C1-6 alkoxy group, 3-10 membered heterocyclyl group, halogeno group, C1-6 alkylene group, substituent G ² , And the substituent G ²¹ is as described above.
Among these, the C6-10 aryl group in G ⁴ is preferably a phenyl group.
The 3- to 10-membered heterocyclyl group in G ⁴ is preferably a 5- to 6-membered heterocyclyl group, more preferably a tetrahydropyranyl group or a pyridyl group.
The substituent G ²¹ in G ⁴ preferably represents a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a halogeno group.

The C2-6 alkenyloxy group is a hydroxyl group substituted with a C2-6 alkenyl group. Examples of the C2-6 alkenyloxy group include a vinyloxy group, a 1-propenyloxy group, and a 2-propenyloxy group (allyloxy group).
Examples of the C3-8 cycloalkyl C1-6 alkyl group include a cyclopropylmethyl group and a cyclopentylmethyl group, and a cyclopropyl C1-6 alkyl group and a cyclopentyl C1-6 alkyl group are preferable.
Examples of the C6-10 aryl C1-6 alkyl group include a benzyl group and a phenethyl group.

The 3- to 10-membered heterocyclyl C1-6 alkyl group is preferably a 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as tetrahydrofuranylmethyl group, tetrahydropyranylmethyl group, dioxolanylmethyl group, dioxanylmethyl group, etc. Groups; 5- to 6-membered heteroaryl C1-6 alkyl groups such as a pyrazolylmethyl group and a pyridylmethyl group. A pyridyl C1-6 alkyl group, a tetrahydropyranyl C1-6 alkyl group, and a pyrazolyl C1-6 alkyl group are preferable.
Examples of the C3-8 cycloalkyloxy C1-6 alkyl group include a cyclopropyloxymethyl group and a cyclohexyloxymethyl group. Preferred are a cyclopropyloxy C1-6 alkyl group and a cyclohexyloxy C1-6 alkyl group.

Examples of the C6-10 aryloxy C1-6 alkyl group include a phenoxymethyl group and a naphthyloxymethyl group, and a phenoxy C1-6 alkyl group is preferable.

The 3- to 10-membered heterocyclyloxy C1-6 alkyl group is preferably a 5- to 6-membered heteroarylmethyl group such as a pyrazolyloxymethyl group and a pyridyloxymethyl group. A pyridyloxy C1-6 alkyl group and a pyrazolyloxy C1-6 alkyl group are preferable.
Examples of the C1-6 alkoxyimino group include a methoxyimino group (MeO-N =) and an ethoxyimino group (EtO-N =).
Examples of the C6-10 aryl C1-6 alkoxyimino group include a benzyloxyimino group (BnO-N =).
Examples of the C1-6 alkyl hydrazino group include a methyl hydrazino group (MeNH-N =) and an ethyl hydrazino group (EtNH-N =).

A part of the substituent G ⁴ on B ^a may be bonded to a carbon atom on Ar ² to form an unsubstituted or G ⁴ -substituted 5- to 6-membered ring. Examples of the 5- to 6-membered ring include a cyclopentene ring, a cyclohexene ring, a tetrahydrofuran ring, a 1,3-dioxolane ring, a tetrahydropyran ring, and the like, preferably a cyclopentene ring, a tetrahydrofuran ring, and a tetrahydropyran ring.

<T ¹ >
T ¹ represents an unsubstituted or G ² -substituted C 6-10 aryl C 1-6 alkoxyimino-C 1-6 alkyl group, or a ferrocenyl-C 1-6 alkyl group.
An unsubstituted or G ² substituted C6-10 aryl C1-6 alkoxyimino-C1-6 alkyl group is a C1-6 alkyl group that is unsubstituted or substituted with G ² C6-10 aryl C1— A 6-alkoxyimino group is substituted.
The C6-10 aryl C1-6 alkoxyimino group is as described above.
C6-10 aryl C1-6 alkoxyimino-C1-6 alkyl group includes benzyloxyimino-methyl group, 1- (benzyloxyimino) -ethyl group, 2- (benzyloxyimino) -1-methylpropyl group, And 2-phenyl-1-methylpropoxyimino) -1-methylpropyl group.
The substituent G ² in T ¹ is as described above, and is preferably a C1-6 haloalkyl group or a C1-6 haloalkoxy group.
Examples of the ferrocenyl-C1-6 alkyl group include a ferrocenylmethyl group.

In the present invention, Q is preferably an organic group represented by formula (II) or formula (III).

B ^a in the organic group represented by the formula (III). Examples of the compound which is unsubstituted or C3 ~ C6 cycloalkylene group substituted by G ^4, compounds of the formula (VI) are preferred.

In formula (VI),
R ¹ , R ² , R ³ , R ⁴ , A, R ^a , G ⁴ , and Ar ² have the same meaning as in formula (I). n represents an integer of 0 to 1.
Among these, R ¹ in the formula (VI) is preferably an unsubstituted C1-6 alkyl group.
R ² in the formula (VI) is preferably an unsubstituted C1-6 alkyl group.

R ³ in formula (VI) preferably represents an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted C 3-8 cycloalkyl group, or an unsubstituted C 6-10 aryl group.
G ¹ in R ³ of the formula (VI) is as described above, and preferably represents a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, or a halogeno group.

R ⁴ in formula (VI) is a hydrogen atom, a C1-6 alkyl group substituted with G ¹ , an unsubstituted C1-6 alkylcarbonyl group, a C6-10 aryl C1-6 alkyl group substituted with G ² , Or it is preferably an unsubstituted C1-6 alkoxycarbonyl group.
G ¹ in R ⁴ of the formula (VI) is as described above, and preferably represents a C1-6 alkoxycarbonyl group, and G ² represents a C1-6 alkoxy group.

R ^a in formula (VI) is preferably ^a hydrogen atom.
G ⁴ in the formula (VI) is preferably a C1-6 alkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, or a C2-6 alkenyloxy group.

Ar ² in formula (VI) is preferably a substituted or substituted C 6-10 aryl group substituted with G ² (more preferably a phenyl group), an unsubstituted or substituted C 2-10 aryloxy group substituted with G ² (More preferably a phenoxy group), an unsubstituted or G ² -substituted 3- to 10-membered heterocyclyl group (more preferably a 5- to 6-membered heteroaryl group, even more preferably a pyridyl group or a pyrazolyl group), or A 3- to 10-membered heterocyclyloxy group (more preferably a 5- to 6-membered heteroaryloxy group, still more preferably a pyridyloxy group) which is unsubstituted or substituted with G ² .
G ² in Ar ² of formula (VI) is as defined above, preferably, C1 ~ 6 haloalkyl group, a tri C1 ~ 6 alkyl silyl ethynyl group, C1 ~ 6 alkoxy group, C1 ~ 6 alkoxy C1 ~ 6 An alkoxy group, a C1-6 haloalkoxy group, or a halogeno group;

The pyridine compound according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the pyridine compound according to the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds and the like, mixtures thereof, and tautomeric organisms.

[Tautomers]
When R ⁴ is a hydrogen atom, the pyridine compound of the present invention gives the following tautomeric pyridine-4-one compound. In the formula, R ¹ , R ² , R ³ , and Q have the same meaning as defined in the formula (I). In the present invention, the tautomeric pyridine-4-one compound is also included in the present invention.

[Stereoisomer]
In the present invention, compounds represented by the same structural formula, but compounds having different spatial arrangements of atoms or substituents in the structure, for example, optical isomers, diastereoisomers, geometric isomers, etc. These stereoisomers are also included in the present invention. The stereoisomer may be a single substance or a mixture.

〔salt〕
The salt of the compound (I) according to the present invention is not particularly limited as long as it is an agro-horticulturally acceptable salt. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron and copper And salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like. The salt of compound (I) can be obtained from compound (I) by a known method.

〔Production method〕
The pyridine compound according to the present invention is not particularly limited by its production method. The pyridine compound according to the present invention can be synthesized by combining known reaction steps. For example, it can be obtained by a production method including the following reaction steps.

First, a compound represented by formula (a) (hereinafter sometimes referred to as “compound (a)”) and a compound represented by formula (b) (hereinafter sometimes referred to as “compound (b)”). ) Is synthesized to synthesize a compound represented by the formula (c) (hereinafter sometimes referred to as “compound (c)”) as a raw material for the next step. Here, in the above formula, R ¹ to R ³ have the same meaning as in formula (I), and R ⁷ and R ⁸ each independently represents an alkyl group or the like.
The amount of compound (b) to be used is generally 0.5 to 2 mol, preferably 0.7 to 1.5 mol, per 1 mol of compound (a).
The synthesis reaction of compound (c) may be performed without a solvent or in a solvent. The solvent used in this reaction is not particularly limited as long as it is inert to the reaction. For example, ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran; aromatic hydrocarbon solvents such as toluene, benzene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent; Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane; Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; Examples thereof include nitrile solvents such as acetonitrile and benzonitrile; alcohol solvents such as methanol, ethanol and n-propanol; and mixed solvents composed of two or more of these.
The reaction temperature is a temperature range from room temperature to the boiling point of the solvent used. The reaction time is usually several minutes to several tens of hours depending on the reaction scale.

Next, the compound (c) and the compound represented by the formula (d) (hereinafter sometimes referred to as “compound (d)”) or the compound represented by the formula (d ′) (hereinafter referred to as “compound ( d ′) ”may be reacted to produce a compound represented by the formula (e) (hereinafter also referred to as“ compound (e) ”). In the above formula, R ¹ to R ³ and R ⁷ have the same meaning as described above. R ⁴ has the same meaning as in formula (I), and L represents a leaving group such as a halogen atom. R ^a and A have the same meaning as in formula (II), (III) or (IV).
The amount of compound (d) or compound (d ′) to be used is generally 0.5 to 2 mol, preferably 0.7 to 1.5 mol, per 1 mol of compound (c).
This reaction can be carried out in a solvent. The solvent is not particularly limited as long as it is inert to the reaction. For example, ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran; aromatic hydrocarbon solvents such as toluene, benzene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent; Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane; Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; Examples thereof include nitrile solvents such as acetonitrile and benzonitrile; alcohol solvents such as methanol, ethanol and n-propanol; and mixed solvents composed of two or more of these.
The amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (c).

Although this reaction can be performed in the absence of a catalyst, it is preferably performed in the presence of a base catalyst.
Base catalysts include triethylamine, diisopropylethylamine, pyridine, 1,2-diazabicyclo [2,2,2] octane (DABCO), 4-dimethylaminopyridine (DMAP), 1,2-diazabiniclo [5,4,0]. Organic bases such as unde-7-ene (DBU) can be used.
The amount of the base catalyst to be used is generally 0.1 to 10 mol per 1 mol of compound (c).
The reaction temperature is a temperature range from room temperature to the boiling point of the solvent used. The reaction time is usually several minutes to several tens of hours depending on the reaction scale.

Next, the compound (e) is reduced to obtain a compound represented by the formula (f) (hereinafter sometimes referred to as “compound (f)”).
As the reducing agent, lithium aluminum hydride, sodium borohydride, diisobutylaluminum hydride and the like can be used.
This reduction reaction can be carried out in a solvent. The solvent is not particularly limited as long as it is inert to the reaction. For example, ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran; aromatic hydrocarbon solvents such as toluene, benzene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent; Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane; Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; Examples thereof include nitrile solvents such as acetonitrile and benzonitrile; alcohol solvents such as methanol, ethanol and n-propanol; and mixed solvents composed of two or more of these.
The amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (e).
The temperature of the reduction reaction is in the temperature range from −78 ° C. to the boiling point of the solvent used. The reaction time is usually several minutes to several tens of hours depending on the reaction scale.

Next, the compound (f) is oxidized to obtain a compound represented by the formula (g) (hereinafter sometimes referred to as “compound (g)”).
As the oxidizing agent, chromium oxide, dichromic acid, chromate ester, pyridinium chlorochromate, manganese dioxide, or the like can be used.
This oxidation reaction can be carried out in a solvent. The solvent is not particularly limited as long as it is inert to the reaction. For example, ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran; aromatic hydrocarbon solvents such as toluene, benzene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent; Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane; Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; Examples thereof include nitrile solvents such as acetonitrile and benzonitrile; and mixed solvents composed of two or more of these.
The amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (f).
The temperature of the oxidation reaction is a temperature range from room temperature to the boiling point of the solvent used. The reaction time is usually several minutes to several tens of hours depending on the reaction scale.

Next, the compound (g) is subjected to various carbon addition reactions to obtain a compound represented by the formula (2) (hereinafter sometimes referred to as “compound (2)”).
The compound represented by the formula (2) is useful as a production intermediate for producing the compound represented by the formula (I) and its N-oxide or a salt thereof.
Carbon increase reactions include (methoxymethyl) triphenylphosphonium chloride, (methoxymethyl) triphenylphosphonium bromide, O, O-diethyl (cyanomethyl) phosphonate, O, O-diethylphosphonoacetic acid methyl ester, (2,2-dimethoxy) Ethyl) -phosphoric acid diethyl ester, diethyl phosphonoacetic acid ethyl ester, diethyl (2,2-diethoxyethyl) phosphonate, (1,3-dioxolan-2-ylmethyl) -phosphoric acid diethyl ester, diethoxy methoxymethyl phosphonate, etc. And Wittig reaction and Horner-Emmons reaction.
This carbon increase reaction can be performed in a solvent. The solvent is not particularly limited as long as it is inert to the reaction. For example, ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran; aromatic hydrocarbon solvents such as toluene, benzene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvents; Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; and mixed solvents composed of two or more of these solvents.
The amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (g).

This carbon increase reaction is preferably performed in the presence of a base.
As the base, an alkali metal base such as sodium hydride, sodium methoxide, sodium ethoxide, potassium t-butoxide and the like can be used.
The amount of the base to be used is generally 1 to 10 mol per 1 mol of compound (g).
The reaction temperature is in the temperature range from −78 ° C. to the boiling point of the solvent used. The reaction time is usually several minutes to several tens of hours depending on the reaction scale.

Finally, the compound represented by the formula (1) (hereinafter referred to as “compound (h)”) is reacted with the compound represented by the formula (1) (hereinafter referred to as “compound (h)”). (Sometimes referred to as “compound (1)”). In the above formula, R ¹ to R ⁴ , R ^a and A have the same meaning as described above. R ⁶ has the same meaning as Ar ¹ , Ar ² -B ^a , or T ¹ in formula (II), (III), or (IV).
The amount of compound (h) to be used is generally 0.5 to 2 mol, preferably 0.7 to 1.5 mol, per 1 mol of compound (2).
The synthesis reaction of the compound (1) can be carried out in the absence of a catalyst, but is preferably carried out in the presence of an acid catalyst or a base catalyst, more preferably in the presence of an acid catalyst.
Examples of the acid catalyst include trifluoroacetic acid, benzenesulfonic acid, p-toluenesulfonic acid, p-toluenesulfonic acid monohydrate, methanesulfonic acid, pyridinium p-toluenesulfonate, hydrochloric acid, sulfuric acid, and the like.
Examples of the base catalyst include pyridine, triethylamine, potassium hydroxide and the like.
The amount of the catalyst to be used is generally 0.0001-1 mol per 1 mol of compound (2).
In addition, a dehydrating agent such as anhydrous sodium sulfate or molecular sieve may be added to the reaction system.

The synthesis reaction of the compound (1) can be performed in a solvent. The solvent is not particularly limited as long as it is inert to the reaction. For example, ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran; aromatic hydrocarbon solvents such as toluene, benzene and xylene; aliphatic hydrocarbons such as n-pentane, n-hexane and n-heptane Solvent; Halogenated hydrocarbon solvent such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane; Amide solvent such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone; Examples thereof include nitrile solvents such as acetonitrile and benzonitrile; alcohol solvents such as methanol, ethanol and n-propanol; and mixed solvents composed of two or more of these.
The amount of the solvent to be used is not particularly limited, but is usually 1 to 100 ml with respect to 1 g of compound (2).
The reaction temperature is a temperature range from room temperature to the boiling point of the solvent used. The reaction time is usually several minutes to several tens of hours depending on the reaction scale.

The salt of the compound (I) according to the present invention can be obtained from the compound represented by the formula (I) by a known method.

In any of the above reactions, the product can be purified after completion of the reaction. Examples of purification means include distillation, recrystallization, and column chromatography.
The structure of the target product can be identified and confirmed by ¹ H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis and the like.

Some intermediates produced in the production process of the compound of the present invention exhibit bactericidal activity.

Since the pyridine compound according to the present invention has effects such as pest control, sterilization, acaricide, and insecticide, it is useful as an agricultural and horticultural fungicide, a pest control agent, and an insecticide or acaricide active ingredient. It is a highly safe compound because it has little phytotoxicity and low toxicity to fish and warm-blooded animals.

[Agricultural and horticultural fungicides, pesticides, and insecticides or acaricides]
The agricultural and horticultural fungicide, pesticide, and insecticide or acaricide of the present invention are effective at least one selected from the compound (I) or a salt thereof (hereinafter sometimes referred to as “the present compound”). It is contained as a component.

The agricultural and horticultural fungicides of the present invention belong to a wide variety of filamentous fungi, for example, algae (Oomycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes Has excellent bactericidal power against bacteria.

Examples of plant diseases and pathogens to be controlled are shown below.
Sugar beet: brown spot (Cercospora beticola), black root (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc. Cucumber: powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), mycotic disease (Sclerotinia sclerotiorum), gray mold disease (Botrytiscine , Anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani Kuhn), spot bacterial disease (Pseudomonas syringae pv. Lecrymans) Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans), half body wilt (Verticillium albo-atrum), etc. Eggplant: Gray Mold disease (Botrytis cinerea), black blight disease (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), subtilis disease (Mycovellosiella nattrassii), mycorrhizal disease (Sclerotinia sclerotiorum), etc. Strawberry: Gray mold disease (Botrytis cinerea), Diseases (Sohaerotheca humuli), anthrax (Colletotrichum acutatum, Colletotrichum fragariae), plagues (Phytophthora cactorum), etc. , Downy mildew (Peronospora destructor), white plague (Phytophthora porri), etc. syringae pv. maculicala, Pseudomonas syringae pv. alisalensis), downy mildew (Peronospora parasitica), mycorrhizal disease (Sclerotinia sclerotiorum), etc. Kidney: Mycosis (Sc) lerotinia sclerotiorum), gray mold (Botrytis cinerea), etc.

Apples: powdery mildew (Podosphaera leucotricha), black spot disease (Venturia inaequalis), monilinia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), rot disease (Valsa mali), spotted leaf disease (Alternaria mali), red star disease (Gymnosporang) yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena), purple coat rot (Helicobasidium mompa), etc. Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), keratodeciduous leaf disease (Cercospora kaki), etc. Peach: Monilinia fructicola, black scab (Cladosporium carpophilum), homoposis Rot disease (Phomopsis sp.), Perforated bacterial disease (Xanthomonas campestris pv. Pruni), etc. Auto: Monilinia fructicola, anthracnose (Colletotrichum acutatum), etc. Grapes: Gray mold Diseases (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black Rot (Guignardia bidwellii), etc. Pear: Venturia nashicola, Red rot (Gymnosporangium asiaticum), Black spot (Alternaria kikuchiana), Ring rot (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali), Body blight (Phomopsis fukushii), brown spot disease (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Cha: ring spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis), etc. , Blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), sunspot (Diaporthe citri), scab (Xanthomonas campestris pv.Citri), etc.

Wheat: powdery mildew (Erysiphe graminis f.sp.Tritici), red mold (Gibberella zeae), red rust (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eyeprint Disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow rot microbe nuclei (Typhula incarnata), snow rot large bacilli (Myriosclerotinia borealis), blight (Gaeumanomyces graminis) Barley: Pyrenophora graminea, Pyrenophora teres, Cloudy disease (Rhynchosporium secalis), Bare smut (Ustilago tritici, U.nuda), etc. Rice: Rice blast (Pyricularia oryzae) Disease (Rhizoctonia solani), idiot seedling disease (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicolum), white leaf blight (Xanthomonas oryzae), seedling blight (Burkholderia plantarii), Brown stripe disease (Acidovorax avenae), bacterial blast blight (Burkholderia glumae), leaf blight (Cercospora oryzae), rice rot (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), black rice (Alternaria padwickii), red rice ( Epicoccam purpurascenns, etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), etc. Tulip: Gray mold, Botrytis cinerea, etc. ), Dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), Red fire (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola), etc. Orchardgrass: powdery mildew (Erysiphe graminis), etc. Soybean: Purple spot (Cercospora) kikuchii), downy mildew (Peronospora Manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyrhizi), mycorrhizal disease (Sc) lerotinia sclerotiorum, anthracnose (Colletotrichum truncatum), etc. Potato: Phytophthora infestans, etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola), etc. Decay disease (Phoma lingam), black spot disease (Alternaria brassicae), etc.

The insecticide or acaricide of the present invention is excellent in the effect of controlling various pests such as various agricultural pests and mites that affect plant growth. The insecticide or acaricide of the present invention is effective not only for susceptible strains but also for pests of strains that have developed resistance to conventional agents such as organophosphorus agents and carbamate agents. Representative examples of pests of resistant strains include goldfish, planthopper, leafhopper, aphid and the like.

The pest control agent of the present invention is effective for controlling pests other than agricultural pests and mites. Examples of pests include ectoparasites and sanitary pests.

Plants that can be targeted by the agricultural and horticultural fungicides, pesticides, and insecticides or acaricides of the present invention include cereals, vegetables, root vegetables, potatoes, trees, grasses, grasses, etc. Is mentioned.
The agricultural and horticultural fungicides, pesticides, and insecticides or acaricides of the present invention are plant parts such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprout, roots, tubers, It can be applied to tuberous roots, shoots and cuttings. In addition, improved varieties and varieties of these plants, cultivated varieties, and mutants, hybrids, and genetically modified organisms (GMO) can also be targeted.

The agricultural and horticultural fungicide of the present invention should be used for seed treatment, foliage application, soil application, water surface application, etc. for controlling various diseases occurring in agricultural and horticultural crops including flower buds, turf, and grass. Can do.

Agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides of the present invention are agricultural and horticultural fungicides that have other effects such as bactericidal, insecticidal / miticidal, nematicidal, soil-killing pests, etc. Agricultural and horticultural agents; plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. may be used in combination or in combination.
An example is shown below.
Fungicide:
(1) Nucleic acid biosynthesis inhibitors:
(A) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race;
(B) Adenosine deamylase inhibitor: bupilimate, dimethylylmol, ethylimol;
(C) DNA / RNA synthesis inhibitors: Himexazole, octirinone;
(D) DNA topoisomerase II inhibitor: oxophosphate;
(2) Mitotic fission inhibitor and cell division inhibitor:
(A) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; ethaboxam;
(B) Cell division inhibitor: Pencyclon;
(C) Delocalization inhibitor of spectrin-like protein: fluopicolide;
(3) Respiratory inhibitor:
(A) Complex INADH oxidoreductase inhibitor: Diflumetrim;
(B) Complex II succinate dehydrogenase: benodanyl, flutolanil, mepronil; isophetamide; fluopyram; fenfram, flumeciclos; carboxin, oxycarboxyl; tifluzamide; , Isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid;
(C) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin; pyraclostrobin, Piramethostrobin, triclopyricarb; Cresoxime-methyl, trifloxystrobin; Dimoxystrobin, Phenaminestrobin, Metominostrobin, Orisastrobin; Famoxadone; Fluoxastrobin; Fenamidon;
(D) Complex III ubiquinol reductase Qi inhibitor: cyazofamide; amisulbrom;
(E) Uncoupler of oxidative phosphorylation: binapacryl, meptyldinocup, dinocup; fluazinam; ferrimzone;
(F) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(G) ATP production inhibitor: silthiofam;
(H) Complex III: Cyclochrome bc1 (ubiquinone reductase) Qx (unknown) inhibitor: Amethoctrazine;

(4) Amino acid and protein synthesis inhibitors (a) Methionine biosynthesis inhibitors: Andprim, cyprodinil, mepanipyrim, pyrimethanil;
(B) Protein synthesis inhibitor: blasticidin-S; kasugamycin, kasugamycin hydrochloride; streptomycin; oxytetracycline;
(5) Signaling inhibitor:
(A) Signaling inhibitor: quinoxyphene, proquinazide;
(B) MAP / histidine kinase inhibitor in osmotic signaling: fenpiclonil, fludioxonil; clozolimate, iprodione, procymidone, vinclozolin;
(6) Lipid and cell membrane synthesis inhibitors:
(A) Phospholipid biosynthesis, methyltransferase inhibitor: Edifenphos, iprobenphos, pyrazophos; isoprothiolane;
(B) lipid peroxidants: biphenyl, chloroneb, dichlorane, kinden, technazen, tolcrofosmethyl; etridiazole;
(C) Agents that act on the cell membrane: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbfocetylate, prothiocarb;
(D) Microbial disturbance of the pathogen cell membrane: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis strain D747 strain;
(E) an agent that disrupts the cell membrane: an extract of Goseika Yupte (Tea Tree);

(7) Cell membrane sterol biosynthesis inhibitors:
(A) Demethylation inhibitor at the C14 position in sterol biosynthesis: Trifolin; Triflumizole, biniconazole;
Azaconazole, viteltanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriazole), fluconazole, fluconazole- Cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, quinconazole, cimeconazole, tebuconazole, tetraconazole, triadimethone, triadimenol, triticonazole; prothioconazole, voriconazole;
(B) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine;
(C) 3-keto reductase agent in C4-position demethylation of sterol biosynthesis system: phenhexamide; fenpyrazamine;
(D) Sterol biosynthetic squalene epoxidase inhibitors: Pyributicarb; Naftifen, Terbinafine;

(8) Cell wall synthesis inhibition (a) Trehalose and inositol biosynthesis agent: Validamycin;
(B) chitin synthase inhibitor: polyoxin, polyoxorim;
(C) Cellulose synthase inhibitor: dimethomorph, furmorph, pyrimorph; Bench Avaricarb, Iprovaricarb, Toluprocarb, Variphenate; Mandipropamide;
(9) Melanin biosynthesis inhibitor (a) Reductase inhibitor of melanin biosynthesis: Fusaride; Pyroxylone; Tricyclazole;
(B) Dehydrase inhibitor of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl;
(10) Host plant resistance inducer:
(A) Agents acting on the salicylic acid synthesis pathway: Acibenzoral-S-methyl;
(B) Others: Probenazole; thiazinyl; isotianil; laminarin;

(11) Agents with unknown activity: Simoxanyl, fosetylaluminum, phosphoric acid (phosphate), teclophthalam, triazoxide, fursulfamide, dichromedin, metasulfocarb, cyflufenamide, metolaphenone, pyriophenone, dodin, dodin free base, fluthianyl;
(12) Agents with multiple action points: copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; farbum, mancozeb, maneb) , Mancopper, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; dicloflurane, tolylfluanid; Quinomethionate; fluorimide;
(13) Other agents: DBEDC, fluorophorpet, guazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofuram, Agrobacterium, betoxazine, diphenylamine, methylisothiocyanate (MITC) , Mildeomycin, Capsaicin, Carvone, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophene, Diphenzoquat, Diphenzoquat methylsulfonate, Flumetober, Focetyl calcium, Focetyl sodium, Irumamycin, Natamycin, Nitrotal Isopropyl, oxamocarb, sodium propamocin, pyrrolnitrin, tebufloquine, torniphanide, zaliramide, Algophase, amicalthiazole (Amicarthiazol) , Oxathiazolium pin proline (Oxathiapiprolin), metiram zinc, benches azole, trichlamide, uniconazole, mill Deo mycin, oxyphencyclimine Ji-in (Oxyfenthiin), Pical -but Ratho box (picarbutrazox);

Insecticides, acaricides, nematicides, soil insecticides:
(1) Acetylcholinesterase inhibitor:
(A) Carbamate series: alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxym, butoxycarboxym, carbaryl, carbofuran, carbosulfan, etiophencarb, fenobucarb, formethanate, furthiocarb, isoprocarb, methiocarb, mesomil, oxamyl, pirimicarb, propoxycarb Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb; phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb;
(B) Organophosphorus: Acephate, azamethiphos, azinephos-ethyl, azinephos-methyl, kazusafos, chlorethoxyphos, chlorfenvinphos, chlormefos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, dimethone-S-methyl, diazinon, Dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethione, etoprophos, famfur, phenamiphos, fenitrothion, fenthion, phostiazet, heptenophos, imisiaphos, isofenphos, isocarbophos, isoxathione, malathione, methalmethione, mecarbamethione Monocrotophos, nared, ometoate, oxydimethone-methyl, parathion, parathion-methyl, phentoe Folate, hosalon, phosmet, phosphamidone, phoxime, pyrimiphos-methyl, propenophos, propetamphos, prothiophos, pyracrofos, pyridafenthion, quinalphos, sulfotep, tebupyrine phos, temefos, terbufos, tetrachlorvinphos, thiomethone, triazophos, trichlorfos, bamidthione;・ Ethyl, BRP, carbophenothion, cyanophenphos, CYAP, dimeton-S-methylsulfone, diariphos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos, phonofos, formotethione, phosmethylan, isazophos, iodofenphos, methacliphos , Pyrimiphos-ethyl, phosphocarb, propaphos, protoate, sulfophos;

(2) GABA-agonist chloride channel antagonists: chlordane, endosulfan, etiprole, fipronil, pyrafluprole, pyriprole; camfechlor, heptachlor;
(3) Sodium channel modulators: Acrinatrin, d-cis-trans allethrin, d-transarethrin, bifenthrin, bioaresulin, bioareslin isomers, violesmethrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, ciphenothrin [(1R) -trans isomer], deltamethrin, enpentrin [(EZ)-( 1R) -isomer], esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, tau-fulvalinate, halfenprox, imipri Phosphorus, cadreslin, permethrin, phenothrin [(1R) -trans isomer], praretrin, pyrethram, resmethrin, silafluophene, tefluthrin, tetramethrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin; allethrin, pyrethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, fulbrocitrinate, flufenprox, methfluthrin, profolifenbut, pyrethmethrin, terraretrin;
(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxafurol, nicotine;
(5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad;
(6) Chloride channel activator: abamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime;

(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; geofenolan, epofenonane, triprene;
(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar;
(9) Homoptera selective feeding inhibitor: flonicamid, pymetrozine;
(10) Mite growth inhibitor: clofentezin, diflovidazine, hexythiazox, etoxazole;
(11) Microbial-derived insect midgut mesentery: Bacillus thuringiensis subsp. Isla elensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Aisawai, Bacillus thuringiensis subsp. Crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1;
(12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, phenbutasine oxide, propargite, tetradiphone;
(13) Oxidative phosphorylation uncoupler: chlorfenapyr, sulframide, DNOC; binapacryl, dinobutone, dinocup;
(14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride; nereistoxin; thiosultap sodium salt, thiocyclam;

(15) Chitin synthesis inhibitor: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, nobarulone, nobiflumuron, teflubenzuron, triflumuron, buprofezin;
(16) Diptera molting disruptors: cyromazine;
(17) Molting hormone receptor agonists: Chromafenozide, halofenozide, methoxyphenozide, tebufenozide;
(18) Octopamine receptor agonist: Amitraz;
(19) Mitochondrial electron transport system complex III inhibitor: acequinosyl, fluacrylpyrim, hydramethylnon;
(20) Mitochondrial electron transport system complex I inhibitor: phenazaquin, fenproxymate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone;
(21) Voltage-gated sodium channel blockers: indoxacarb, metaflumizone;
(22) Acetyl CoA carboxylase inhibitor: spirodiclofen, spiromesifen, spirotetramat;
(23) Mitochondrial electron transport system complex IV inhibitor: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
(24) Mitochondrial electron transport system complex II inhibitor: sienopyrafen, cyflumetofen;
(25) Ryanodine receptor modulators: chlorantraniliprole, cyantraniprole, fulvendiamide;
(26) Mixed function oxidase inhibitor compound: piperonyl butoxide;
(27) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;

(28) Other agents (the mechanism of action is unknown): azadirachtin, benzoximate, biphenazate, bromopropyrate, quinomethionate, cryolite, dicophor, pyridalyl, pyrifluquinazone; Propene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, fluphenazine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, tetrasulfur, trialacene Afidopyropen, piflubumide, furometokin, flufiprole, fluenesulfone, meperfluthuri , Tetramethylfluthrin, tralopyryl, dimefluthrin, methylneodecanamide; fluralaner, 5- [5- (3,5-dichlorophenyl) -5-trifluoro-4,5-dihydroisooxal-3-yl] -2 -(1H-1,2,4-triazol-1-yl) benzonitrile (CAS: 943137-49-3), 2'-bromo-2-fluoro-4 '-(heptafluoropropan-2-yl)- 3- (N-methylbenzamide) -6 ′-(trifluoromethyl) benzanilide (CAS: 1207727-04-5), other metadiamides;

[Prescription formulation]
The agricultural and horticultural fungicide, pest control agent, and insecticide or acaricide of the present invention are not particularly limited depending on the dosage form. Examples include dosage forms such as wettable powders, emulsions, aqueous solvents, granular wettable powders, powders, and tablets. The preparation method to a formulation is not specifically limited, A well-known preparation method can be employ | adopted according to a dosage form.
In the following, the pharmaceutical formulation is shown slightly, but the additives and addition ratios are not limited to these examples, and can be varied in a wide range. The part in a formulation prescription shows a mass part.

(Formulation 1: wettable powder)
Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts The above components were mixed uniformly and finely pulverized to obtain a wettable powder of 40% active ingredient.

(Formulation 2: Emulsion)
Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts The above components were mixed and dissolved to obtain an emulsion containing 30% active ingredient.

(Formulation 3: Granules)
Compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts The above ingredients are uniformly mixed and finely pulverized, then granulated into granules having a diameter of 0.5 to 1.0 mm, and the active ingredient is 5%. Get the granules.

(Formulation 4: Granules)
Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctylsulfosuccinate sodium salt 1 part Potassium phosphate 1 part The above components are pulverized and mixed well, water is added and kneaded, granulated and dried, and then 5% active ingredient. Get the granules.

(Formulation 5: Suspension)
Compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts A 10% component suspension is obtained.

Next, the present invention will be described more specifically by showing examples. However, the present invention is not limited by the following examples.

Example 1
Production of 1- (4-acetoxy-2,5,6-trimethylpyridin-3-yl) acetaldehyde-O- {2- (4-trifluoromethylphenyl) ethyl} oxime (Compound 2-105) (Step 1)
Synthesis of ethyl 4-hydroxy-2,5,6-trimethylnicotinate

45 g of ethyl 3-aminocrotonate and 50 g of ethyl 2-methylacetoacetate were dissolved in 100 ml of xylene, and the resulting mixed solution was heated to reflux overnight. Thereafter, the reaction solution was cooled to room temperature, and the precipitated crystals were filtered. The obtained crystals were washed with diethyl ether. Thereafter, it was dried to obtain 24.2 g of the objective compound. Yield 33%.
¹ H-NMR (CDCl ₃ , δppm) 1.21 (3H, t), 2.14 (3H, s), 2.46 (3H, s), 2.71 (3H, s), 4.45 (2H, q), 12.14 (3H, s ).

(Process 2)
Synthesis of ethyl 4-allyloxy-2,5,6-trimethylnicotinate

12.2 g of ethyl 4-hydroxy-2,5,6-trimethylnicotinate was dissolved in 120 ml of acetonitrile. To this solution, 16.1 g of potassium carbonate and then 14.1 g of allyl bromide were added, and the resulting mixed solution was heated to reflux for 8 hours. Thereafter, the reaction solution was cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated brine. Then, it dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 10.0 g of the target compound. Yield 77%.
¹ H-NMR (CDCl ₃ , δppm) 1.36 (3H, t), 2.15 (3H, s), 2.46 (6H, s), 4.35-4.40 (5H, m), 5.25-5.39 (2H, m), 5.92 -6.11 (1H, m).

(Process 3)
Synthesis of (4-allyloxy-2,5,6-trimethylpyridin-3-yl) -methanol

2.8 g of lithium aluminum hydride was added to 300 ml of tetrahydrofuran. To this suspension, 10.0 g of ethyl 4-allyloxy-2,5,6-trimethylnicotinate was added dropwise under ice cooling. After completion of dropping, the mixture was stirred at room temperature for 2 hours. Thereafter, the reaction solution was ice-cooled, water was added until unreacted lithium aluminum hydride was decomposed, and the mixture was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 7.9 g of the target compound. Yield 97%.
¹ H-NMR (CDCl ₃ , δppm) 2.18 (3H, s), 2.45 (3H, s), 2.56 (3H, s), 4.38 (2H, d), 4.70 (2H, s), 5.25-5.39 (2H , m), 5.92-6.11 (1H, m).

(Process 4)
Synthesis of 4-allyloxy-2,5,6-trimethylpyridine-3-carbaldehyde

7.9 g of (4-allyloxy-2,5,6-trimethylpyridin-3-yl) -methanol was dissolved in 90 ml of benzene. To this solution, 15.2 g of manganese dioxide was added and heated to reflux overnight. Thereafter, the reaction solution was cooled to room temperature and filtered through Celite (registered trademark). The obtained filtrate was concentrated under reduced pressure to obtain 5.98 g of the target compound. Yield 77%.
¹ H-NMR (CDCl ₃ , δppm) 2.20 (3H, s), 2.51 (3H, s), 2.73 (3H, s), 4.42 (2H, d), 5.25-5.39 (2H, m), 5.92-6.11 (1H, m), 10.48 (1H, s).

(Process 5)
Synthesis of 4-allyloxy-3-[(E) -2-methoxyvinyl] -2,5,6-trimethyl-pyridine

23.5 g of (methoxymethyl) triphenylphosphonium chloride was suspended in 200 ml of tetrahydrofuran (THF), and 75 ml of 1M potassium-t-butoxide THF solution was slowly added dropwise under ice-cooling. Stir. To this reaction solution, 10.3 g of 4-allyloxy-2,5,6-trimethylpyridine-3-carbaldehyde was added under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was then poured into ice water and extracted with ethyl acetate. Subsequently, the mixture was washed with saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 10.4 g of the objective compound. Yield 88%.
¹ H-NMR (CDCl ₃ , δppm) 2.14 (3H, s), 2.42 (3H, s), 2.47 (3H, s), 3.68 (3H, s), 4.26 (2H, d), 5.25-5.41 (2H , m), 5.66 (1H, d), 5.92-6.11 (1H, m), 7.02 (1H, d).

(Step 6)
Synthesis of 2- (4-allyloxy-2,5,6-trimethyl-3-pyridyl) acetaldehyde

4-Allyloxy-3-[(E) -2-methoxyvinyl] -2,5,6-trimethyl-pyridine (5.0 g) was dissolved in THF (100 ml). To this solution, 30 ml of 10% hydrochloric acid was added and stirred at 50 ° C. for 4 hours. Thereafter, the reaction solution was poured into ice water, neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. Subsequently, the mixture was washed with saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 4.6 g of the objective compound.
Yield 95%.
¹ H-NMR (CDCl ₃ , δppm) 2.17 (3H, s), 2.39 (3H, s), 2.46 (3H, s), 3.73 (2H, s), 4.25 (2H, d), 5.25-5.40 (2H , m), 5.97-6.10 (1H, m), 9.70 (1H, s).

(Step 7)
Synthesis of 2- (4-allyloxy-2,5,6-trimethyl-3-pyridyl) -N- [2- [4- (trifluoromethyl) phenyl] ethoxy] ethanamine

1.3 g of O- {2- (4-trifluoromethylphenyl) ethyl} hydroxylamine was dissolved in 20 ml of dichloromethane. To this solution were added 1.4 g of 2- (4-allyloxy-2,5,6-trimethyl-3-pyridyl) acetaldehyde and a few drops of trifluoroacetic acid, and the mixture was stirred overnight at room temperature. Thereafter, the reaction solution was poured into saturated aqueous sodium hydrogen carbonate and extracted with chloroform. Thereafter, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 1.8 g of the objective compound. Yield 68%.

(Process 8)
Synthesis of 4-hydroxy-2,5,6-trimethylpyridine-3-acetaldehyde-O- {2- (4-trifluoromethylphenyl) ethyl} oxime

1.35 g of 2- (4-allyloxy-2,5,6-trimethyl-3-pyridyl) -N- [2- [4- (trifluoromethyl) phenyl] ethoxy] ethanamine was dissolved in 15 ml of methanol. To this solution, 0.04 g of tetrakistriphenylphosphine palladium and 1.38 g of potassium carbonate were added and stirred at room temperature for 2 hours. Thereafter, the reaction solution was poured into ice water, extracted with chloroform, washed with saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with diethyl ether to obtain 1.0 g of the desired compound. Yield 82%.
¹ H-NMR (CDCl ₃ , δppm) 1.99-2.34 (9H, m), 2.93-3.02 (2H, m), 3.49-3.51 (2H, m), 4.12-4.28 (2H, m), 6.67,7.35 ( 1H, t), 7.25-7.50 (4H, m).

(Step 9)
Synthesis of 1- (4-acetoxy-2,5,6-trimethylpyridin-3-yl) acetaldehyde-O- {2- (4-trifluoromethylphenyl) ethyl} oxime

4-hydroxy-2,5,6-trimethylpyridine-3-acetaldehyde-0.7 g of O- {2- (4-trifluoromethylphenyl) ethyl} oxime was dissolved in 10 ml of chloroform. To this solution, 0.39 g of triethylamine was added. Thereafter, 0.30 g of acetyl chloride was added under ice cooling, and the mixture was stirred overnight at room temperature. Next, the reaction solution was poured into saturated aqueous sodium hydrogen carbonate and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.70 g of the target compound. Yield 90%.

(Example 2)
[3- [2- [2-[[3-Chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1-methyl-propoxy] iminoethyl] -2-ethyl-5,6-dimethyl-4 -Pyridyl] acetate (compound 6-80) production (step 1)
Synthesis of methyl 4-hydroxy-2-ethyl-5,6-dimethylnicotinate

13.6 g of methyl-3-aminopent-2-enoate and 20.0 g of 2,2,5,6-tetramethyl-4H-1,3-dioxin-4-one were mixed and stirred at 150 ° C. for 5 hours. did. After cooling to room temperature, the precipitated crystals were filtered, washed with diethyl ether, and then dried to obtain 13.7 g of the target compound. Yield 31%.
¹ H-NMR (CDCl ₃ , δppm) 1.21 (3H, t), 2.14 (3H, s), 2.46 (3H, s), 2.71 (2H, q), 3.89 (3H, s).

(Process 2)
Synthesis of methyl 4-allyloxy-2-ethyl-5,6-dimethylnicotinate

13.7 g of methyl 4-hydroxy-2-ethyl-5,6-dimethylnicotinate was dissolved in 150 ml of acetonitrile. To this reaction solution, 18.2 g of potassium carbonate and then 15.8 g of allyl bromide were added, and the mixture was heated to reflux for 8 hours. The reaction solution was cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 16.6 g of the target compound. Yield 100%.
¹ H-NMR (CDCl ₃ , δppm) 1.25 (3H, t), 2.16 (3H, s), 2.48 (3H, s), 2.69 (2H, q), 3.88 (3H, s), 4.39 (2H, d ), 5.23-5.39 (2H, m), 5.93-6.05 (1H, m).

(Process 3)
Synthesis of (4-allyloxy-2-ethyl-5,6-dimethylpyridin-3-yl) -methanol

2.8 g of lithium aluminum hydride was added to 300 ml of tetrahydrofuran. To this reaction liquid, 16.6 g of methyl 4-allyloxy-2-ethyl-5,6-dimethylnicotinate was added dropwise under ice cooling. After completion of the addition, the mixture was stirred at room temperature for 2 hours. Thereafter, the reaction solution was ice-cooled, water was added until unreacted lithium sodium hydride was decomposed, and the mixture was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 11.3 g of the target compound. Yield 77%.
¹ H-NMR (CDCl ₃ , δppm) 1.26 (3H, t), 2.16 (3H, s), 2.46 (3H, s), 2.84 (2H, q), 4.39 (2H, d), 4.70 (2H, d ), 5.29-5.45 (2H, m), 6.03-6.14 (1H, m).

(Process 4)
Synthesis of 4-allyloxy-2-ethyl-5,6-dimethylpyridine-3-carbaldehyde

11.3 g of (4-allyloxy-2-ethyl-5,6-dimethylpyridin-3-yl) -methanol is dissolved in 120 ml of dichloromethane, and 120 ml of saturated aqueous sodium hydrogen carbonate, 0.6 g of potassium bromide, 4 0.4 g of -oxo-TEMPO was added. To this reaction solution, 91 g of a 5% sodium hypochlorite solution was added dropwise over 30 minutes under ice cooling. After completion of dropping, the mixture was stirred at 0 ° C. for 30 minutes, and the reaction solution was poured into ice water. The mixture was extracted with dichloromethane, washed with an aqueous sodium thiosulfate solution and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 11.1 g of the objective compound. Yield 99%.
¹ H-NMR (CDCl ₃ , δppm) 1.25 (3H, t), 2.21 (3H, s), 2.52 (3H, s), 3.06 (2H, q), 4.42 (2H, d), 5.32-5.43 (2H , m), 6.01-6.11 (1H, m), 10.47 (1H, s).

(Process 5)
Synthesis of 4-allyloxy-3- (2-methoxyvinyl) -2-ethyl-5,6-dimethyl-pyridine

6.57 g of (methoxymethyl) triphenylphosphonium chloride was suspended in 40 ml of THF, and 19.2 ml of 1M potassium-t-butoxide THF solution was slowly added dropwise under ice cooling. After completion of the addition, the mixture was stirred for 1 hour under ice cooling. . To this reaction solution, 2.8 g of 4-allyloxy-2-ethyl-5,6-dimethylpyridine-3-carbaldehyde was added under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with ethyl acetate, washed with saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 1.0 g of the desired compound. Yield 32%.
¹ H-NMR (CDCl ₃ , δppm) 1.21 (3H, t), 2.14 (3H, s), 2.44 (3H, s), 2.70 (2H, q), 3.63 (3H, s), 4.32 (2H, d ), 5.25-5.42 (3H, m), 5.96-6.09 (1H, m), 6.14 (1H, d).

(Step 6)
Synthesis of 2- (4-allyloxy-2-ethyl-5,6-dimethyl-3-pyridyl) acetaldehyde

0.4 g of 4-allyloxy-3- (2-methoxyvinyl) -2-ethyl-5,6-dimethyl-pyridine was dissolved in 4 ml of THF. To this reaction solution, 1.6 ml of 10% hydrochloric acid was added and stirred at 60 ° C. for 4 hours. The reaction mixture was poured into ice water, neutralized with sodium bicarbonate, extracted with ethyl acetate, washed with saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.37 g of the objective compound. Yield 98%.
¹ H-NMR (CDCl ₃ , δppm) 1.19 (3H, t), 2.17 (3H, s), 2.47 (3H, s), 2.66 (2H, q), 3.72 (2H, s), 4.25 (2H, d ), 5.25-5.40 (2H, m), 5.95-6.08 (1H, m), 9.70 (1H, s).

(Step 7)
2- (4-Allyloxy-2-ethyl-5,6-dimethyl-3-pyridyl) -N- [2-[[3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1- Synthesis of methyl-propoxy] ethanimine

0.57 g of O- [2-[[3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1-methyl-propyl] hydroxylamine was dissolved in 5 ml of dichloromethane. To this solution were added 0.37 g of 2- (4-allyloxy-2-ethyl-5,6-dimethyl-3-pyridyl) acetaldehyde and a few drops of trifluoroacetic acid, and the mixture was stirred overnight at room temperature. The reaction solution was poured into saturated aqueous sodium hydrogen carbonate and extracted with chloroform, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.53 g of the objective compound. Yield 67%.
¹ H-NMR (CDCl ₃ , δppm) 1.17-1.43 (9H, m), 2.14-2.76 (8H, m), 2.95-3.04 (2H, m), 3.49-4.42 (5H, m), 5.21-6.09 ( 4H, m), 6.55-8.30 (3H, m).

(Process 8)
3- [2- [2-[[3-Chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1-methyl-propoxy] iminoethyl] -2-ethyl-5,6-dimethyl-pyridine- Synthesis of 4-ol (compound 6-30)

2- (4-Allyloxy-2-ethyl-5,6-dimethyl-3-pyridyl) -N- [2-[[3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1- 0.53 g of methyl-propoxy] ethanimine was dissolved in 10 ml of methanol. To this solution were added 0.012 g of tetrakistriphenylphosphine palladium and 0.44 g of potassium carbonate, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into ice water, extracted with chloroform, washed with saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with diethyl ether to obtain 0.50 g of the target compound. Yield 99%.

(Step 9)
[3- [2- [2-[[3-Chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1-methyl-propoxy] iminoethyl] -2-ethyl-5,6-dimethyl-4 -Pyridyl] acetate synthesis

3- [2- [2-[[3-Chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1-methyl-propoxy] iminoethyl] -2-ethyl-5,6-dimethyl-pyridine- 0.46 g of 4-ol was dissolved in 10 ml of chloroform. After adding 0.21 g of triethylamine to this solution, 0.16 g of acetyl chloride was added under ice cooling, followed by stirring at room temperature overnight. The reaction solution was poured into saturated aqueous sodium hydrogen carbonate and extracted with chloroform, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.25 g of the target compound. Yield 49%.

Compounds prepared by the same method as in the above examples are shown in Tables 1 to 8 and Table 10. In addition, the physical property data of the compounds are described in the “Physical Properties” column. As the physical property data, melting point (° C.), refractive index (nD), or properties thereof are described.
Table 1 shows compounds represented by formula (I) in which Q is an organic group represented by formula (II) (compound represented by formula (I-1) shown below). Disclose.
Here, the compounds described in Table 1 are compounds in which R ¹ , R ² , and R ³ are methyl groups.
“E” shown in “stereoconfiguration” indicates that the double bond of imine in the compound is E configuration. “Z” indicates a Z configuration. “EZ” indicates that the compound is a mixture of compounds in both configurations (the same meaning is given in the following tables).
In the table, Ph represents a phenyl group. Similarly, Me represents a methyl group, Et represents an ethyl group, and Ac represents an acetyl group (the same meaning is shown in the following tables).

Tables 2 to 8 are compounds represented by formula (I), wherein Q is an organic group represented by formula (III) (shown by formula (I-2) shown below) Compound).
The compounds listed in Table 2 are compounds in which R ¹ , R ² , and R ³ are methyl groups.
The carbon marked with * in the structural formula in “B ^a ” represents carbon bonded to oxygen of the oxime (the same meaning is shown in the following tables). Furthermore, the carbon marked with ** in the structural formula of “B ^a ” of the compound 2-186 and the compound 2-187 represents a carbon bonded to “Ar ² ”.
“Trans” shown in “stereoconfiguration” indicates that the 1,4-cyclohexylene group in the compound is in the trans configuration.
In the table, Py represents a pyridyl group, ⁿ Pr represents an n-propyl group, ⁱ Pr represents an isopropyl group, ^c Pr represents a cyclopropyl group, ^c Pen represents a cyclopentyl group, and ^c Hex represents a cyclohexyl group (hereinafter referred to as a cyclohexyl group). The same meaning is also shown in the table).

The compounds listed in Table 3 are compounds in which R ¹ , R ² , and R ³ are methyl groups. ^N Bu in the table represents an n-butyl group (the same meaning is given in the following tables).

The compounds listed in Table 4 are compounds in which R ¹ , R ² , and R ³ are methyl groups.
The oxygen marked with * in the structural formula in “A” indicates that it binds to the pyridine ring (the same meaning is shown in the following tables).
“E, EZ” shown in “stereoconfiguration” indicates that the compound is a mixture of a compound in which the ethynylene group in “A” is in the E configuration and the imine double bond is in the E configuration and a compound in the Z configuration. .

The carbons marked with ** in the structural formulas of “B ^a ” of Compound 5-19 and Compound 5-48 represent carbons bonded to “Ar ² ”.
“Trans” shown in “stereoconfiguration” indicates that the 1,3-cyclopentylene group, 1,3-cyclohexylene group or 1,4-cyclohexylene group in the compound is in the trans configuration. “Cis” indicates that a 1,3-cyclopentylene group, a 1,3-cyclohexylene group or a 1,4-cyclohexylene group is in a cis configuration (the same meaning is given in the following tables). .

“B ^a ” of Compound 6-7, Compound 6-8, Compound 6-9, Compound 6-10, Compound 6-55, Compound 6-56, Compound 6-57, Compound 6-58, and Compound 6-59 The carbon marked with ** in the structural formula represents a carbon that is bonded to “Ar ² ”.
In the table, ^t Bu represents a t-butyl group (the same meaning is given in the following tables).

* In the partial structural formulas shown below in Table 8, * indicates the bonding position with “A”.

The partial structural formulas corresponding to “* 1” to “* 17” in Table 8 are listed in Table 9 below.

Table 10 shows compounds represented by formula (I) in which Q is an organic group represented by formula (IV) (compound represented by formula (I-3) shown below). Disclose.
The compounds listed in Table 10 are compounds in which R ¹ , R ² , and R ³ are methyl groups.

In addition, the following compounds are in a stereoisomeric relationship.
2-15 and 2-16, 2-109 and 2-110, 3-21 and 3-22, 3-23 and 3-24, 3-42 and 3-43, 3-46 and 3-47, 3- 68 and 3-69, 3-88 and 3-89, 3-94 and 3-95, 3-126 and 3-127, 3-129 and 3-130, 3-131 and 3-132, 4-22 4-23, 4-34 and 4-35, 4-38 and 4-39, 4-40 and 4-41, 8-69 and 8-71, 8-70 and 8-72, 8-75 and 8- 76.

Table 11 shows ¹ H-NMR data for some of the compounds described in Tables 1 to 8 and 10 above.

[Biological test]
The following test examples show that the compounds of the present invention are useful as active ingredients of agricultural and horticultural fungicides.
(Test Example 1) Wheat powdery mildew control test First, 95 parts by mass of dimethylformamide containing 1.5% by mass of polyoxyethylene sorbitan monolaurate and 5 parts by mass of the compound of the present invention were mixed and dissolved to obtain an active ingredient. A 5% emulsion was prepared.
The above-mentioned emulsion was diluted with water containing 0.02% by mass of polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm to prepare a test drug solution. Subsequently, the test chemical solution was sprayed on wheat seedlings (variety “Chihoku”, 1.0-1.2 leaf stage) cultivated in an unglazed pot. After the leaves were air-dried, conidia of wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) were shaken off and inoculated in a greenhouse at 22 to 25 ° C. for 7 days (treatment). On the other hand, the seedlings of wheat powdery mildew fungus were shaken off and inoculated on the leaves of wheat seedlings (variety “Chihoku”, 1.0-1.2 leaf stage) grown in an unglazed pot without spraying the test chemical solution. It was kept in a greenhouse at -25 ° C for 7 days (no treatment). The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
As a result, the compounds shown in Table 12 below exhibited an excellent control value of 75% or more.

(Test Example 2) Wheat red rust control test The emulsion described in Test Example 1 was diluted with water containing 0.02% by mass of polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm, and the test was performed. A drug solution was prepared. Subsequently, the test chemical solution was sprayed on wheat seedlings (variety “Noribayashi No. 61”, 1.0 to 1.2 leaf stage) cultivated in an unglazed pot. After air-drying the leaves, summer spores of wheat red rust fungus (Puccinia recondita) were shaken off and inoculated in a greenhouse at 22-25 ° C. for 10 days. In the same manner as in Test Example 1, the lesion appearance state on the leaves was compared with no treatment to determine the control effect.
As a result, the compounds shown in Table 13 below exhibited an excellent control value of 75% or more.

Next, the following test examples show that the compounds of the present invention are useful as active ingredients of insecticides or acaricides.
(Test Example 3) Efficacy Confirmation Test for Lotus Spodoptera First, 5 parts by mass of the compound of the present invention, 93.6 parts by mass of dimethylformamide, and 1.4 parts by mass of polyoxyethylene alkylaryl ether were mixed and dissolved, and the active ingredient was 5%. An emulsion was prepared.
The emulsion was diluted with water to a compound concentration of 125 ppm. Cabbage leaves were dipped in the chemical solution for 30 seconds, air-dried, placed in a petri dish with filter paper, and 5 second-instar larvae of Spodoptera litura were inoculated. The glass lid was put on and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. After 5 days, the survival was examined and the insecticidal rate was determined. The test is duplicated. As a result, the compounds shown in Table 14 below showed an insecticidal rate of 100%.

(Test Example 4) Efficacy Confirmation Test for Cotton Aphid Adult cotton aphids were inoculated on the first true leaf of cucumber 10 days after germination seeded in a 3-inch pot. One day later, the adults were removed, and a chemical solution obtained by diluting the emulsion described in (Test Example 3) with water so that the compound concentration was 125 ppm was sprayed on the cucumber infested with the nymphs produced. It was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The test is duplicated. As a result, the compounds shown in Table 15 below showed an insecticidal rate of 100%.

(Test Example 5) Efficacy confirmation test against nymph mite Ten adult nymph mites were inoculated on the first true leaf of green beans that had been sown for 10 days after being sown in 3-inch pots. One day later, a chemical solution diluted with water was sprayed so that the emulsion compound concentration described in (Test Example 3) was 125 ppm. It was placed in a temperature-controlled room with a temperature of 25 ° C. and a humidity of 65%. The test is duplicated. As a result, the compounds shown in Table 16 below showed an insecticidal rate of 100%.

(Test Example 6) Efficacy test against Acacia toyo 0.2 ml of commercially available artificial feed (Insector LFS, manufactured by Nippon Nosan Kogyo Co., Ltd.) was packed in a plastic test tube (1.4 ml volume) to prepare test materials. The emulsion described in (Test Example 3) was diluted with water so that the compound concentration was 125 ppm, and the chemical solution was dropped onto the feed surface in an amount equivalent to 10 μg of the compound. Two instar larvae were inoculated per test tube and sealed with a plastic lid. The specimen was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. As a result, the compounds shown in Table 17 below showed an insecticidal rate of 100%.

(Test Example 7) Efficacy test against bean aphids Adult bean aphids were released on large square beans that had been sown in 3-inch pots and 10 days after germination. After 1 day, the 1st instar nymphs that were born were left and the adults were removed. The emulsion described in (Test Example 3) was diluted with water so that the compound concentration was 125 ppm, and the chemical solution was sprayed onto the large square beans. Thereafter, the large angle beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%, and the survival of the bean aphid was examined after 5 days to determine the insecticidal rate. As a result, the compounds shown in Table 18 below showed an insecticidal rate of 80% or more.

(Test Example 8) Efficacy test against Kanzawa spider mite Five adult female Kanzawa spider mites were released on the primary leaves 7 to 10 days after germination of mung beans seeded in a 3-inch pot. The emulsion described in Test Example 3 was diluted with water so that the compound concentration was 125 ppm, and the chemical solution was sprayed on the mung beans. Thereafter, the mung beans were placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. As a result, the compounds shown in Table 19 below showed an insecticidal rate of 80% or more.

The pyridine compound according to the present invention is a novel compound that has effects such as pest control, bactericidal, acaricidal, insecticidal and the like, does not cause phytotoxicity on plants, and has little toxicity to human fish and environmental impacts. . In particular, it exhibits an excellent control effect against wheat diseases. The pyridine compound according to the present invention is useful as an active ingredient of agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.

Claims

A compound represented by formula (I) or a salt thereof.

In formula (I),
R 1 represents a hydrogen atom, an unsubstituted or C 1-6 alkyl group substituted with G 1 , or a halogeno group.
R 2 and R 3 are each independently an unsubstituted or G 1 -substituted C 1-6 alkyl group, an unsubstituted or G 1 -substituted C 3-8 cycloalkyl group, an unsubstituted or G 2 A C6-10 aryl group substituted with or a halogeno group.
R 4 is a hydrogen atom, an unsubstituted or C1 ~ 6 alkyl group substituted with G 1, unsubstituted or C2 ~ 6 alkenyl group substituted with G 1, which is substituted by unsubstituted or G 1 C2 substituted 1-6 alkynyl group, an unsubstituted or C3 ~ 8 cycloalkyl group substituted with G 1, unsubstituted or C6 ~ 10 aryl C1 to 6 alkyl group substituted with G 2, unsubstituted or with G 2 3- to 10-membered heterocyclyl group C1-6 alkyl group, formyl group, C1-6 alkylcarbonyl group which is unsubstituted or substituted with G 1 , C6-10 arylcarbonyl group which is unsubstituted or substituted with G 2 , unsubstituted or C1 ~ 6 alkoxycarbonyl group substituted with G 1, unsubstituted or C2 ~ 6 alkenyloxycarbonyl group substituted with G 1, unsubstituted or G A C1-6 alkylsulfonyl group substituted with 1 , a C1-6 alkylaminocarbonyl group unsubstituted or substituted with G 1 , a (C1-6 alkylthio) carbonyl group unsubstituted or substituted with G 1 , or A C1-6 alkylamino (thiocarbonyl) group which is unsubstituted or substituted with G 1 or a group represented by the formula (V) is shown.

In formula (V),
G a independently represents a hydrogen atom, an unsubstituted or C1 ~ 6 alkyl group substituted with G 1, unsubstituted or C2 ~ 6 alkenyl group substituted with G 1, unsubstituted or with G 1 substituted C2 ~ 6 alkynyl group, a unsubstituted or C3 ~ 8 cycloalkyl group substituted by G 1 or unsubstituted or C6 ~ 10 aryl group substituted by G 2,.
G b represents a hydrogen atom, an unsubstituted or C1 ~ 6 alkyl group substituted with G 1, unsubstituted or C2 ~ 6 alkenyl group substituted with G 1, which is substituted by unsubstituted or G 1 C2 2-6 alkynyl group, an unsubstituted or C3 ~ 8 cycloalkyl group substituted with G 1, unsubstituted or C6 ~ 10 aryl group substituted by G 2 3 or substituted with unsubstituted or G 2, Represents a 10-membered heterocyclyl group;
T is an oxygen atom, oxycarbonyl group, carbonyloxy group, oxycarbonyloxy group, sulfur atom, (thio) carbonyl group, carbonyl (thio) group, (thio) carbonyloxy group, oxycarbonyl (thio) group, or- A divalent group represented by O—C (═O) —N (G b ) — is shown.
* Indicates the bonding position of the group represented by the formula (V).
G 1 is a hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyloxy group, C1-6 alkoxycarbonyloxy group, cyano A group or a halogeno group.
G 2 is a C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C1-6 haloalkyl group, C1-6 alkoxy C1-6 alkyl group, tri C1-6 alkyl Silyl C1-6 alkyl group, Tri C1-6 alkylsilyl C2-6 alkynyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group , C1-6 haloalkoxy group, C2-6 alkenyloxy group, C2-6 alkynyloxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyloxy group C1-6 alkoxycarbonyloxy group, C1-6 alkoxycarbonylamino group, The or C6 ~ 10 aryl group substituted by G 21, unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkyl group substituted with G 21, unsubstituted or C6 ~ 10 aryloxy group which is substituted by G 21 , unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxy group substituted by G 21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 21, 3 substituted with unsubstituted or G 21 ~ 10-membered heterocyclyl C1-6 alkyl group, 3-10 membered heterocyclyloxy group, unsubstituted or substituted with G 21 , C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 Haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, cyano group, nitro group, halogeno group , C1-6 alkylene group, C1-6 alkylenedioxy group, or C1-6 haloalkylenedioxy group.
G 21 represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a cyano group, a nitro group, or a halogeno group.
Q represents any one of the organic groups represented by the formulas (II) to (IV).

In formulas (II) to (IV),
Ar 1 represents an unsubstituted or C6 ~ 10 aryl group substituted by G 2 or unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 2,.
Ar 2 is unsubstituted or C6 ~ 10 aryl group substituted by G 2, unsubstituted or C6 ~ 10 aryloxy group which is substituted by G 2, C6 ~ 10 substituted with unsubstituted or G 2 aryl C1 ~ 6 alkoxy group, an unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 2, unsubstituted or 3-10 membered heterocyclyloxy group substituted with G 2 or unsubstituted or G 2, A substituted 3- to 10-membered heterocyclylthio group is shown.
R a represents a hydrogen atom, an amino group, an unsubstituted or substituted C 1-6 alkyl group with G 1 , or an unsubstituted or substituted C 2-10 aryl group with G 2 .
A is unsubstituted or C1 ~ C6 alkylene group substituted with G 3, unsubstituted or C2 ~ C6 alkenylene group substituted with G 3, unsubstituted or C2 ~ C6 alkynylene group substituted with G 3 shows the unsubstituted or C1 ~ C6 alkylene group which is substituted by G 3, unsubstituted or is oxy C1 ~ C6 alkylene group substituted with G 3, unsubstituted C3 ~ C6 cycloalkylene group or a carbonyl group, .
G 3 is a C1-6 alkyl group, C1-6 alkoxy group, formyl group, C1-6 alkylcarbonyl group, formyloxy group, C1-6 alkylcarbonyloxy group, halogeno group, C1-6 alkylene group, or oxo group Indicates.
B a is unsubstituted or C1 ~ C6 alkylene group substituted with G 4, unsubstituted or C2 ~ C6 alkenylene group substituted with G 4, unsubstituted or C2 ~ C6 alkynylene substituted with G 4 group, an unsubstituted or C3 ~ C6 cycloalkylene group substituted by G 4, unsubstituted or C4 ~ C6 cycloalkenylene group substituted with G 4 3 ~ 6 or of unsubstituted or substituted by G 4, The group represented by a membered heterocyclylene group is shown.
G 4 is a C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group , C1 ~ 6 haloalkoxy group, C2 ~ 6 alkenyloxy group, an unsubstituted or C6 ~ 10 aryl group substituted by G 21, unsubstituted or 3-10 membered heterocyclyl group which is substituted by G 21, a cyano group , Halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C3-8 cycloalkyl C1-6 alkyl group, unsubstituted or substituted with G 21 C6-10 aryl C1-6 alkyl group, an unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxy group substituted by G 21, 3 ~ 10 membered f substituted with unsubstituted or G 21 Roshikuriru C1 ~ 6 alkyl group, C3 ~ 8 cycloalkyloxy C1 ~ 6 alkyl group, unsubstituted or C6 ~ 10 aryloxy C1 ~ 6 alkyl group substituted with G 21, which is substituted by unsubstituted or G 21 3-10 membered heterocyclyloxy C1 ~ 6 alkyl group, a C1 ~ 6 alkoxyimino group, an unsubstituted or C6 ~ 10 aryl C1 ~ 6 alkoxyimino group substituted by G 21 or C1 ~ 6 alkyl hydrazino group, .
Part of a substituent G 4 on B a may form a 5- or 6-membered ring with the carbon atom on Ar 2.
T 1 represents an unsubstituted or G 2 -substituted C 6-10 aryl C 1-6 alkoxyimino-C 1-6 alkyl group, or a ferrocenyl-C 1-6 alkyl group.
* Indicates the bonding position of the organic group represented by formula (II) to formula (IV).
An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.
A pest control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.
An insecticide or acaricide containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.