JPWO2015199065A1 - Pyridine compounds and uses thereof - Google Patents

Abstract

In the present invention, R 1, R 2, R 3, and R 4 each independently represent a hydrogen atom, a C 1-6 alkyl group, etc. R 1 and R 2 are taken together to form R 1 and R 2 You may form a 5-6 membered ring with the carbon atom to which Q couple | bonds. Q is a formula (II) (In formula, Ar1 shows a C6-10 aryl group etc. Ra is a hydrogen atom, C1-6 alkyl. * Represents a bonding position of the organic group represented by the formula (II))) or a salt thereof, and the compound and the compound Provided is an agricultural and horticultural fungicide, pesticide or insecticide or acaricide containing at least one selected from the group consisting of salts as an active ingredient. [Chemical 1] [Chemical 2]

Description

  The present invention relates to pyridine compounds and uses such as agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.

  In the cultivation of agricultural and horticultural crops, many control agents have been proposed for crop diseases, but their use is limited or 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.

  By the way, 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.

WO 2003/103667 A

  An object of the present invention is to provide a novel pyridine compound, and 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 is hydrogen atom, an unsubstituted or C1~6 alkyl group substituted with G ^1, unsubstituted or C1~6 alkoxy group substituted with G ^1, which is substituted by unsubstituted or G ² C6 10 aryl group, an unsubstituted or 3-6 membered heterocyclyl group which is substituted by G ^2, a cyano group or a halogeno group.
R ² and R ³ are each independently a hydrogen atom, an unsubstituted or C1~6 alkyl group substituted with G ^1, unsubstituted or C3~8 cycloalkyl group substituted by G ^1, the unsubstituted or Cl to 6 alkoxy group substituted with G ^1, a formyl group, a formyloxy group, an unsubstituted or Cl to 6 alkyl group substituted with G ^1, which is substituted by unsubstituted or G ¹ Cl to 6 alkylcarbonyloxy group, an unsubstituted or C6~10 aryl groups substituted with G ^2, (unsubstituted or substituted with G ¹ a C1~6 alkoxyimino)-C1-6 alkyl group, a cyano group or a halogeno, Indicates a group.
Here, R ¹ and R ² may be combined to form a 5- to 6-membered ring together with the carbon atom to which R ¹ and R ² are bonded.
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 6 alkynyl group, substituted with unsubstituted or C3~8 cycloalkyl group substituted with G ^1, unsubstituted or C6~10 aryl C1~6 alkyl group substituted with G ^2, unsubstituted or G ² It has been 3-6 membered heterocyclyl group, an unsubstituted or 3-6 membered heterocyclyl group C1~6 alkyl group substituted with G ^2, a formyl group, an unsubstituted or C1~6 alkylcarbonyl group substituted by G ¹ , unsubstituted or C3~8 cycloalkylcarbonyl group substituted with G ^1, unsubstituted or C1~6 alkenylcarbonyl group substituted with G ^1, unsubstituted or with G ² is substituted And C6~10 aryl carbonyl group, an unsubstituted or C1~6 alkoxycarbonyl group substituted with G ^1, unsubstituted or C2~6 alkenyloxycarbonyl group substituted with G ^1, unsubstituted or with G ¹ substituted Cl to 6 alkylsulfonyl group, unsubstituted or Cl to 6 alkylaminocarbonyl group substituted with G ^1, unsubstituted or substituted with G ¹ a (Cl to 6 alkylthio) carbonyl group, the unsubstituted Or a C1-6 alkylamino (thiocarbonyl) group substituted by G ¹ or a group represented by the formula (IV).

Wherein (IV), G ^a are independently a hydrogen atom, an unsubstituted or C1~6 alkyl group substituted with G ^1, unsubstituted or C2~6 alkenyl group substituted with G ^1, no showing a substituted by a substituted or G ¹ a C2~6 alkynyl group, an unsubstituted or C3~8 cycloalkyl group substituted by G ¹ or unsubstituted or C6~10 aryl groups substituted with G ^2, .

Wherein (IV), 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, unsubstituted or G C2~6 alkynyl group substituted with ^1, unsubstituted or C3~8 cycloalkyl group substituted with G ^1, unsubstituted or C6~10 aryl groups substituted with G ² or unsubstituted or G, ² represents a 3-6 membered heterocyclyl group substituted with ² .

In the formula (IV), T represents an oxygen atom, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio) carbonyl group, a carbonyl (thio) group, a (thio) carbonyloxy group, an oxycarbonyl ( Thio) group or a divalent group represented by —O—C (═O) —N (G ^b ) —.
* Indicates the bonding position of the group represented by the formula (IV).

  Q represents either an organic group represented by formula (II) or formula (III).

[In Formula (II) and Formula (III),
Ar ¹ represents an unsubstituted or C6~10 aryl groups substituted with 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 with G ^2, unsubstituted or C6-10 aryloxy group which is substituted by G ^2, substituted with unsubstituted or G ² C6-10 arylthio group, an unsubstituted or C6~10 arylsulfinyl group substituted by G ^2, unsubstituted or C6~10 arylsulfonyl group substituted with G ^2, substituted with unsubstituted or G ² 3 to 10 membered heterocyclyl group, an unsubstituted or 3-10 membered heterocyclyloxy group which is substituted by G ^2, unsubstituted or 3-10 membered heterocyclylthio group or a ferrocenyl group substituted with G ^2.
R ^a is a hydrogen atom, an unsubstituted or Cl to 6 alkyl group substituted with G ^1, unsubstituted or C3~8 cycloalkyl group substituted with G ^1, amino group, Cl to 6 alkylcarbonylamino group , or unsubstituted or showing a C6~10 aryl group substituted by G ^2.
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 C1~C6 alkyleneoxy C1~6 alkylene group substituted with G ^4, unsubstituted or C3~C6 cycloalkylene group substituted by G ^4, which is substituted unsubstituted or at G ⁴ C1~C6 alkylene C3~6 cycloalkylene group, an unsubstituted or substituted by G ⁴ a C1~C6 alkyleneoxy C3~6 cycloalkylene group, an unsubstituted or C4~C6 cycloalkenylene group substituted with G ^4, Or a 3-6 membered heterocyclylene group which is unsubstituted or substituted with G ⁴ .
Further, ^a carbon atom of B ^a or ^a part of the substituent G ⁴ on B ^a may be bonded to a carbon atom on Ar ² to form a 5- to 6-membered ring.
* Indicates the bonding position of the organic group represented by formula (II) or formula (III). ]

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 A group or a halogeno group. R ^1, R ^2, R ^3, when two or more of R ⁴ or R ^a is the radical which is substituted by G ^1, G ¹ according may be the same or different from each other .

G ² is a C 1-6 alkyl group, a hydroxy C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-8 cycloalkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy C 1-6 alkyl. Group, C1-6 alkoxy C1-6 haloalkyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C3-8 cycloalkyl C1-6 alkoxy group, C1-6 alkoxyC1 -6 alkoxy group, C1-6 haloalkoxy group, C1-6 haloalkoxy C1-6 haloalkoxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyl Oxy group, C1-6 alkoxycarbonyloxy group, C1-6 alkoxycarbonyl Amino group, an unsubstituted or C6~10 aryl groups substituted with G ^21, unsubstituted or C6~10 aryl C1~6 alkyl group substituted with G ^21, which is substituted by unsubstituted or G ²¹ C6 10 aryloxy group, an unsubstituted or 3-6 membered heterocyclyl group which is substituted by G ^21, unsubstituted or 3-6 membered heterocyclyloxy group which is substituted by G ^21, Cl to 6 alkylthio group, Cl to 6 alkylsulfinyl groups, Cl to 6 alkylsulfonyl group, Cl to 6 haloalkylthio group, Cl to 6 haloalkylsulfinyl group, Cl to 6 haloalkylsulfonyl group, a pentafluorosulfanyl group, substituted with unsubstituted or G ²¹ C6-10 An arylthio group, an unsubstituted or a C6-10 arylsulfinyl group substituted with G ²¹ , unsubstituted or Shows C6~10 arylsulfonyl group substituted with G ^21, a nitro group, a cyano group, a halogeno group, Cl to 6 alkylene group, a Cl to 6 alkylenedioxy group or a Cl to 6 halo alkylenedioxy group. ^{R 1, R 2, R 3} , R 4, R a, if two or more of G ^4, Ar ¹ or Ar ² is said group substituted with G ^2, G ² according are mutually They may be the same or different.

G ²¹ represents a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, or a halogeno group. If more than one of G ² or G ⁴ is a said group substituted with G ^21, G ²¹ according may be the same or different from each other.

G ⁴ are, Cl to 6 alkyl, C3-8 cycloalkyl, Cl to 6 haloalkyl, Cl to 6 alkoxy Cl to 6 alkyl groups, C2-6 alkenyloxy Cl to 6 alkyl groups, hydroxyl, Cl to 6 alkoxy group, Cl to 6 alkoxy Cl to 6 alkoxy, C2-6 alkenyloxy group, substituted with Cl to 6 alkoxy carbonyl group, an unsubstituted or C6~10 aryl groups substituted with G ^21, unsubstituted or G ²¹ been 3-6 membered heterocyclyl group, a cyano group, a halogeno group, Cl to 6 alkylene groups, Cl to 6 alkylenedioxy group, an oxo group, C3-8 cycloalkyl Cl to 6 alkyl groups, unsubstituted or with G ²¹ substituted C6~10 aryl C1~6 alkyl, 3-6 membered heterocyclyl C1~6 alkyl substituted with unsubstituted or G ²¹ Group, C3-8 cycloalkyloxy C1~6 alkyl group, an unsubstituted or C6~10 aryloxy C1~6 alkyl group substituted with G ^21, unsubstituted or 3-6 membered heterocyclyl optionally substituted with G ²¹ oxy Cl to 6 alkyl groups, Cl to 6 alkylidene group, Cl to 6 alkoxyimino group, an unsubstituted or C6~10 aryl Cl to 6 alkoxyimino group substituted with G ^{2 1} or Cl to 6 alkyl hydrazino group, Indicates. ]

[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 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.

  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 is hydrogen atom, an unsubstituted or C1~6 alkyl group substituted with G ^1, unsubstituted or C1~6 alkoxy group substituted with G ^1, which is substituted by unsubstituted or G ² C6 -10 aryl group, 3-6 membered heterocyclyl group, cyano group or halogeno group.
The C1-6 alkyl group may be a straight chain or a branched chain as long as 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 can be mentioned.
As C1-6 alkoxy groups, methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group , T-butoxy group, i-hexyloxy group and the like.

  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.

  The 3- to 6-membered heterocyclyl group contains 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring constituent atoms. 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 3-6 membered heterocyclyl group include a 3-6 membered saturated heterocyclyl group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heterocyclyl group, and the like.

  Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, tetrahydropyranyl group, dioxolanyl group, dioxanyl Examples include groups.

Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl Can do.
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridanidyl group, and a triazinyl group.
Examples of the halogeno group include a fluoro group, a chloro group, a bromo group, and an iodo group.

Substituents G ¹ is hydroxyl, Cl to 6 alkoxy, Cl to 6 alkoxy Cl to 6 alkoxy, Cl to 6 alkoxycarbonyl group, a formyloxy group, Cl to 6 alkylcarbonyloxy group, Cl to 6 alkoxycarbonyloxy group , A cyano group, or a halogeno group. In the case two or more of ^{R 1, R 2, R 3} , R 4 or R ^a is been substituted with G ^1, according G ¹ may be the same or different from each other .

The C1-6 alkoxy group and the halogeno group in the substituent G ¹ are as described above.
Examples of the C1-6 alkoxy 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 substituent G ² is a C 1-6 alkyl group, a hydroxy C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-8 cycloalkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy C 1- 6 alkyl group, C1-6 alkoxy C1-6 haloalkyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C3-8 cycloalkyl C1-6 alkoxy group, C1-6 Alkoxy C1-6 alkoxy group, C1-6 haloalkoxy group, C1-6 haloalkoxy C1-6 haloalkoxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 Alkylcarbonyloxy group, C1-6 alkoxycarbonyloxy group, C1-6 alkoxycal Niruamino group, an unsubstituted or C6~10 aryl groups substituted with G ^21, unsubstituted or C6~10 aryl C1~6 alkyl group substituted with G ^21, C6 substituted with unsubstituted or G ²¹ 10 aryloxy group, an unsubstituted or 3-6 membered heterocyclyl group which is substituted by G ^21, unsubstituted or 3-6 membered heterocyclyloxy group which is substituted by G ^21, Cl to 6 alkylthio group, Cl to 6 alkylsulfinyl groups, Cl to 6 alkylsulfonyl group, Cl to 6 haloalkylthio group, Cl to 6 haloalkylsulfinyl group, Cl to 6 haloalkylsulfonyl group, a pentafluorosulfanyl group, substituted with unsubstituted or G ²¹ C6-10 arylthio group, an unsubstituted or C6~10 arylsulfinyl group substituted by G ^21, unsubstituted Or C6~10 arylsulfonyl group substituted with G ^21, a nitro group, a cyano group, a halogeno group, Cl to 6 alkylene group, a Cl to 6 alkylenedioxy group or a Cl to 6 halo alkylenedioxy group.

C1-6 alkyl group, C1-6 alkoxy group, C1-6 alkoxy C1-6 alkoxy group, C1-6 alkoxycarbonyl group, C1-6 alkylcarbonyloxy group, C1-6 alkoxycarbonyloxy group in the substituent G ² , C6-10 aryl group, 3-6 membered heterocyclyl group and halogeno group are as described above.

Examples of the hydroxy C1-C6 alkyl group include a hydroxymethyl group, a hydroxyethyl group, and a hydroxypropyl group.
Examples of the C2-6 alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -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, 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 -A dimethyl-2-butynyl group etc. can be mentioned.
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.

The C1-6 alkoxy C1-6 alkyl group is the above-described C1-6 alkoxy group substituted on the C1-6 alkyl group already described. Examples of the C1-6 alkoxy C1-6 alkyl group include methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i -A propoxyethyl group, a s-butoxymethyl group, a t-butoxyethyl group, etc. can be mentioned.
The C3-8 cycloalkyl C1-6 alkoxy group is the above-described C3-8 cycloalkyl group substituted on the C1-6 alkoxy group already described. Examples of the C3-8 cycloalkyl C1-6 alkoxy group include a cyclopropylmethoxy group, a cyclobutylmethoxy group, a cyclopentylmethoxy group, a cyclohexylmethoxy group, and a 2- (cyclopropyl) -ethoxy group.

  The C1-6 alkylcarbonyl group is obtained by bonding the above-described C1-6 alkyl group 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 obtained by substituting the aforementioned C6-10 aryl group for the C1-6 alkyl group already described. 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 3-6 membered heterocyclyloxy group is a group in which a 3-6 membered heterocyclyl group is substituted on the hydroxyl group. Examples of the 3- to 6-membered heterocyclyloxy group include a pyrazolyloxy group and a pyridyloxy group. The 3-6 membered heterocyclyloxy group is preferably a 5-6 membered heterocyclyloxy group.
A 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 a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group, and an i-butylthio group.
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, a t-butylsulfonyl group, and the like.
A C6-10 arylthio group is obtained by substituting a C6-10 aryl group for an SH group. Examples of the C6-10 arylthio group include a phenylthio group and a naphthylthio group.
The C6-10 arylthio group is a sulfanyl group substituted with a C6-10 aryl group. Examples of the C6-10 arylthio group include a phenylthio group and a naphthylthio group.
A C6-10 arylsulfinyl group is a sulfinyl group substituted by a C6-10 aryl group. Examples of the C6-10 arylsulfinyl group include a phenylsulfinyl group and a naphthylsulfinyl group.
A C6-10 arylsulfonyl group is a sulfonyl group substituted by a C6-10 aryl group. Examples of the C6-10 arylsulfonyl group include a phenylsulfonyl group and a naphthylsulfonyl 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 (dimethylene 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 in which two hydrogen atoms in a C1-6 alkane are substituted 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 2,3-dihydro-benzo [1,4] dioxyl group, benzo [1,3] dioxolyl group, and the like. Can do.

The C1-6 haloalkyl group, the C2-6 haloalkenyl group, the C2-6 haloalkynyl group, the C1-6 haloalkoxy group, and the C1-6 haloalkylenedioxy group are the C1-6 alkyl groups, C2-6 A 6-alkenyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, and a C1-6 alkylenedioxy group are substituted with a halogeno group.
As C1-6 haloalkyl group, 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, A 2,2-trifluoro-1-trifluoromethylethyl group, a perfluorohexyl group, a perchlorohexyl group, a 2,4,6-trichlorohexyl group, and the like can be given.

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 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, and 5-bromo-2-pentynyl group.
Examples of the C1-6 haloalkoxy group include chloromethoxy group, dichloromethoxy group, difluoromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2- Trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, pentafluoroethoxy group, 2,2,3,4,4,4-hexafluoro-butoxy group, 1-bromo-1,1,2 , 2-tetrafluoroethoxy group and the like.
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 with a C1-6 haloalkylenedioxy group as G ² include a 2,2,3,3-tetrafluoro-2,3-dihydro-benzo [1,4] dioxyl group, Examples include 2,2-difluoro-benzo [1,3] dioxolyl group.

A C1-6 alkoxy C1-6 haloalkyl group, a C1-6 haloalkoxy C1-6 haloalkoxy group, a C1-6 haloalkylthio group, a C1-6 haloalkylsulfinyl group, and a C1-6 haloalkylsulfonyl group, -6 alkoxy C1-6 alkyl group, C1-6 alkoxy C1-6 alkoxy group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, and C1-6 alkylsulfonyl group are substituted with a halogeno group.
Examples of the C1-6 alkoxy C1-6 haloalkyl group include a difluoro (methoxy) methyl group and a 1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl group.
Examples of the C1-6 haloalkoxy group include a difluoro (methoxy) methoxy group and a 1,2,2-trifluoro-2- (trifluoromethoxy) ethoxy group.
Examples of the C1-6 haloalkylthio group include a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.
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.

The substituent G ²¹ represents a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, or a halogeno group. These are as already described.
If more than one of G ² or G ⁴ is a said group substituted with G ^21, G ²¹ according may be the same or different from each other.

  In the present invention, R1 is a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group substituted with G1 (preferably unsubstituted), an unsubstituted or substituted alkoxy group with G1 (preferably unsubstituted). A C6-10 aryl group (preferably a phenyl group) which is unsubstituted or substituted with G2 (preferably a C1-6 alkoxy group, a C1-6 alkoxycarbonyloxy group), an unsubstituted or a G2 substituted 6 member A ring heteroaryl group (preferably an unsubstituted pyridyl group), a cyano group or a halogeno group is preferred, and an unsubstituted C1-6 alkyl group or a halogeno group is more preferred.

[R ² and R ³ ]
R ² and R ³ are each independently a hydrogen atom, an unsubstituted or C1~6 alkyl group substituted with G ^1, unsubstituted or C3~8 cycloalkyl group substituted by G ^1, the unsubstituted or Cl to 6 alkoxy group substituted with G ^1, a formyl group, a formyloxy group, an unsubstituted or Cl to 6 alkyl group substituted with G ^1, which is substituted by unsubstituted or G ¹ Cl to 6 alkylcarbonyloxy group, an unsubstituted or C6~10 aryl groups substituted with G ^2, (unsubstituted or substituted with G ¹ a C1~6 alkoxyimino)-C1-6 alkyl group, a cyano group or a halogeno, Indicates a group.
In R ² and R ³ , a C1-6 alkyl group, a C3-8 cycloalkyl group, a C1-6 alkoxy group, a C1-6 alkylcarbonyl group, a C1-6 alkylcarbonyloxy group, a C6-10 aryl group, a halogeno group, And the substituents G ¹ and G ² are as described above.
Examples of the (C1-6 alkoxyimino) -C1-6 alkyl group include a methoxyimino-methyl group and a 1- (ethoxyimino) -ethyl group.

R ¹ and R ² may together form a 5-6 membered ring with the carbon atom to which each of R ¹ and R ² is attached. Examples of such a 5- to 6-membered ring include a cyclopentene ring and a cyclohexene ring.

In the present invention, R ² is a hydrogen atom, unsubstituted or G ¹ (preferably a hydroxyl group, a halogeno group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group. C1~6 alkyl group substituted with), substituted with unsubstituted or C1~6 alkoxy group substituted with G ¹ (preferably unsubstituted), unsubstituted or G ² (preferably C1~6 alkoxy group) been C6~10 aryl groups (preferably phenyl group), an unsubstituted or C1~6 alkylcarbonyl group substituted with G ¹ (preferably unsubstituted), C1 to substituted with (unsubstituted or G ¹ 6 alkoxyimino) -C1-6 alkyl group (preferably unsubstituted), halogeno group, cyano group, and formyl group are preferable, and unsubstituted C1-6 alkyl group is more preferable. preferable.
In the present invention, R ³ is unsubstituted or substituted with G ¹ (preferably a hydroxyl group, a halogeno group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group). It has been C1~6 alkyl group, an unsubstituted or C1~6 alkoxy group substituted with G ¹ (preferably unsubstituted), unsubstituted C3~8 cycloalkyl group (preferably 3-4 cycloalkyl group), unsubstituted or C1~6 alkylcarbonyloxy group substituted with G ¹ (preferably unsubstituted), unsubstituted or C6~10 aryl groups substituted with G ² (preferably an unsubstituted phenyl group), ( unsubstituted or C1~6 alkoxyimino substituted with G ^1)-C1-6 alkyl group (preferably unsubstituted), a halogeno group, a cyano group or a formyl group Preferably, a C1-6 alkyl group or a halogeno group which is unsubstituted or substituted with G1 (preferably a hydroxyl group, a halogeno group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group) More preferred.

[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 6 alkynyl group, substituted with unsubstituted or C3~8 cycloalkyl group substituted with G ^1, unsubstituted or C6~10 aryl C1~6 alkyl group substituted with G ^2, unsubstituted or G ² been 3-6 membered heterocyclyl group, an unsubstituted or 3-6 membered heterocyclyl C1~6 alkyl group substituted with G ^2, a formyl group, an unsubstituted or C1~6 alkylcarbonyl group substituted with G ^1, unsubstituted or C3~8 cycloalkylcarbonyl group substituted with G ^1, unsubstituted or C1~6 alkenylcarbonyl group substituted with G ^1, is substituted by unsubstituted or G ² C6~10 arylcarbonyl group, substituted with unsubstituted or C1~6 alkoxycarbonyl group substituted with G ^1, unsubstituted or C2~6 alkenyloxycarbonyl group substituted with G ^1, unsubstituted or G ¹ been Cl to 6 alkylsulfonyl group, unsubstituted or Cl to 6 alkylaminocarbonyl group substituted with G ^1, unsubstituted or substituted with G ¹ (Cl to 6 alkylthio) carbonyl group, an unsubstituted or A C1-6 alkylamino (thiocarbonyl) group substituted with G ¹ or a group represented by the formula (IV) is shown.

In R ⁴ , C1-6 alkyl group, C2-6 alkenyl group, C2-6 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl C1-6 alkyl group, 3-6 membered heterocyclyl group, C1-6 alkyl The carbonyl group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, substituent G ¹ and substituent G ² are as described above.

The 3-6 membered heterocyclyl C1-6 alkyl group is a C1-6 alkyl group substituted with a 3-6 membered heterocyclyl group. The 3- to 6-membered heterocyclyl C1-6 alkyl group is preferably a 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as a tetrahydrofuranylmethyl group, a tetrahydropyranylmethyl group, a dioxolanylmethyl group, a dioxanylmethyl group, or the like. Group; 5-6 membered heteroaryl C1-6 alkyl groups, such as a pyrazolylmethyl group and a pyridylmethyl group, can be mentioned.
The C3-8 cycloalkylcarbonyl group is obtained by bonding the aforementioned C3-8 cycloalkyl group to a carbonyl group. Examples of the C3-8 cycloalkylcarbonyl group include a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, and a cyclohexylcarbonyl 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 alkenylcarbonyl group include an acryloyl group and a methacryloyl group.
Examples of the C2-6 alkenyloxycarbonyl group include a vinyloxycarbonyl group, a 1-propenyloxycarbonyl group, a 2-propenyloxycarbonyl group (allyloxycarbonyl group), and the like.
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.

[In the formula (IV),
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, an unsubstituted or C3~8 cycloalkyl group substituted by G ¹ or unsubstituted or C6~10 aryl groups substituted with 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 -6 alkynyl group, unsubstituted or G ³ substituted C 3-8 cycloalkyl group, unsubstituted or G ² substituted C 6-10 aryl group, or unsubstituted or G ² substituted 3 Represents a 6-membered heterocyclyl group;
T is an oxygen atom, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio) carbonyl group, a carbonyl (thio) group, a (thio) carbonyloxy group, an oxycarbonyl (thio) group, or a formula : -OC (= O) -N ( ^Gb )-.
* Indicates the bonding position of the group represented by the formula (IV). ]

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

In the present invention, R ⁴ is C 1-6 substituted with a hydrogen atom, unsubstituted or G ¹ (preferably a C 1-6 alkylcarbonyloxy group, a C 1-6 alkoxycarbonyloxy group, a halogeno group). An alkyl group, a C2-6 alkenyl group which is unsubstituted or substituted with G ¹ (preferably unsubstituted), a C6-10 aryl C1 which is unsubstituted or substituted with G ² (preferably a C1-6 alkoxy group) 6 alkyl group (preferably benzyl group), unsubstituted or C 1-6 alkylcarbonyl group substituted with G ¹ (preferably C 1-6 alkoxy group, C 1-6 alkylcarbonyloxy group), unsubstituted or G ¹ A C1-6 alkoxycarbonyl group substituted with (preferably unsubstituted), an unsubstituted or a C2-6 alkenylcarbonyl substituted with G ¹ Le group (preferably unsubstituted), unsubstituted or Cl to 6 alkylaminocarbonyl group substituted with G ¹ (preferably unsubstituted), substituted with unsubstituted or G ¹ (Cl to 6 alkylthio) carbonyl Preferably a heterocyclyl group (preferably a 3-6 membered saturated heterocyclyl group) which is unsubstituted or substituted by G ² (preferably a hydroxyl group, a hydroxy C1-6 alkyl group), or a hydrogen atom. A C1-6 alkyl group which is unsubstituted or substituted with G ¹ (preferably a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group), an unsubstituted or G ¹ (preferably a C1-6 alkoxy group). , Cl to 6 alkyl carbonyl group substituted by Cl to 6 alkylcarbonyloxy group) or unsubstituted or G ^1, Conversion has been C1~6 alkoxycarbonyl group is more preferable.
[Q]
Q represents either an organic group represented by formula (II) or formula (III). In addition, * shows the coupling | bonding position of the organic group represented by Formula (II) or Formula (III).

<R ^a >
R ^a is a hydrogen atom, an unsubstituted or Cl to 6 alkyl group substituted with G ^1, unsubstituted or C3~8 cycloalkyl group substituted with G ^1, amino group, Cl to 6 alkylcarbonylamino group , or unsubstituted or showing a C6~10 aryl group substituted by G ^2.
The C1-6 alkyl group, C3-8 cycloalkyl group, C6-10 aryl group, substituent G ¹ and substituent G ² in R ^a are as described above.
The C1-6 alkylcarbonylamino group is a group in which the above-described C1-6 alkylcarbonyl group is substituted on the amino group. Examples of the C1-6 alkylcarbonylamino group include an acetylamino group and a propionylamino group.
In the present invention, as R ^a , a hydrogen atom, an unsubstituted alkyl group, an unsubstituted C 3-8 cycloalkyl group (preferably a C 3-4 cycloalkyl group), an amino group, a C 1-6 alkylcarbonylamino group, A C6-10 aryl group (preferably a phenyl group) which is unsubstituted or substituted with G ² (preferably a C1-6 haloalkyl group) is preferred, and an unsubstituted alkyl group or a hydrogen atom is more preferred.

<Ar ¹ >
Ar ¹ represents an unsubstituted or C6~10 aryl groups substituted with G ² or unsubstituted or 3-10 membered heterocyclyl group which is substituted by G ^2,.
The C6-10 aryl group in Ar ¹ and the substituent G ² are as described above.
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 3-10 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 group such as piperidyl group, piperazinyl group, morpholinyl group, tetrahydropyranyl 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.

Preferred examples of the 3- to 10-membered heterocyclyl group in Ar ¹ include 5- to 10-membered heteroaryl groups such as a pyrazolyl group, a pyridyl group, a pyrimidinyl group, and a quinolinyl group.

In the present invention, Ar ¹ is an unsubstituted or G ² -substituted C 6-10 aryl group (preferably a phenyl group, a naphthyl group) or an unsubstituted or G ² -substituted 5-6 membered heteroaryl. preferably group (preferably pyridyl group), more preferably a pyridyl group substituted with a phenyl group or an unsubstituted or G ² substituted with unsubstituted or G ^2.
G ² in Ar ¹ is a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 alkoxy C 1-6 haloalkyl group, a C 1-6 haloalkoxy group, a C 1-6 alkoxycarbonyl group, substituted or ^{G 21} (preferably C1~6 haloalkyl group) C6-10 aryl group substituted with (preferably phenyl group), substituted with unsubstituted or ^{G 21} (preferably C1~6 haloalkyl group) C6 10 aryl Cl to 6 alkyl group (preferably a benzyl group), an unsubstituted or ^{G 21} (preferably Cl to 6 haloalkyl group) C6-10 aryloxy group substituted (preferably a phenoxy group), Cl to 6 Haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, pentaf Orosurufaniru group, unsubstituted or ^{G 21} (preferably C1~6 haloalkyl group) C6-10 arylthio group (preferably a phenylthio group) that is substituted with, unsubstituted or ^{G 21} (preferably C1~6 haloalkyl group) A C6-10 arylsulfinyl group (preferably a phenylsulfinyl group) substituted with a C6-10 arylsulfonyl group (preferably a phenylsulfonyl group) which is unsubstituted or substituted with G ²¹ (preferably a C1-6 haloalkyl group) , A nitro group, a C1-6 haloalkylenedioxy group and / or a halogeno group,
More preferably, Cl to 6 alkyl, Cl to 6 haloalkyl, Cl to 6 haloalkoxy group, C6-10 aryloxy group (preferably substituted with unsubstituted or ^{G 21} (preferably Cl to 6 haloalkyl group) Is a phenoxy group) and / or a halogeno group.

<Ar ² >
Ar ² is unsubstituted or C6-10 aryl group substituted with G ^2, unsubstituted or C6-10 aryloxy group which is substituted by G ^2, substituted with unsubstituted or G ² C6-10 arylthio group, an unsubstituted or C6~10 arylsulfinyl group substituted by G ^2, unsubstituted or C6~10 arylsulfonyl group substituted by G ^2, 3 to 10 substituted with unsubstituted or G ² It shows a membered heterocyclyl group, unsubstituted or G ² in substituted 3- to 10-membered heterocyclyloxy group unsubstituted or 3-6 membered heterocyclylthio group or a ferrocenyl group substituted with G ^2.
The C6-10 aryl group in Ar ² is as described above, and is preferably phenyl.
The C6-10 aryloxy group is as described above, and is preferably phenoxy.
The 3- to 10-membered heterocyclyl group is as described above, preferably a 5- to 10-membered heteroaryl group, more preferably a thiazolyl group, a triazolyl group, a pyrazolyl group, a pyridyl group, a pyridazinyl group, a quinolyl group. It is.
A 3- to 10-membered heterocyclyloxy group is a hydroxyl group substituted with a 3- to 10-membered heterocyclyl group. As a 3-10 membered heterocyclyloxy group, a 5-6 membered saturated heterocyclyloxy group and a 5-6 membered heteroaryloxy group are preferable.
As the 5- to 6-membered heteroaryloxy group, a pyrazolyloxy group, a pyridyloxy group, a pyridazinyloxy group, and a pyrimidinyloxy group are more preferable.
The 3- to 10-membered heterocyclylthio group is obtained by substituting a 3- to 10-membered heterocyclyl group for the SH group. Examples of the 3- to 10-membered heterocyclylthio group include 5- to 6-membered heteroarylthio groups such as a pyrazolylthio group and a pyridylthio group, and a pyridylthio group is preferable.
The C6-10 arylthio group is as described above, and is preferably a phenylthio group.
The arylsulfinyl group is as described above, and is preferably phenylsulfinyl.
The arylsulfonyl group is as described above, and is preferably phenylsulfonyl.

The substituent G ² is as described above, and preferably a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 3-8 cycloalkyl C 1-6 alkoxy group (preferably a C 3-6 4 cycloalkylalkoxy group), C1-6 haloalkoxy group, C6-10 aryl group which is unsubstituted or substituted with G ²¹ (preferably phenyl group), C6-10 aryl which is unsubstituted or substituted with G ²¹ An oxy group (preferably a phenoxy group), an unsubstituted or G ²¹ -substituted 5- to 6-membered heterocyclyl group (preferably a pyridyl group), an unsubstituted or substituted G ²¹ -substituted 5 to 6-membered heterocyclyloxy group ( Preferably a pyridyloxy group), a pentafluorosulfanyl group, a cyano group, a halogeno group, or a C1-6 haloalkylene group. A group.
As G ^2, more preferably, Cl to 6 haloalkyl group, Cl to 6 alkoxy, Cl to 6 haloalkoxy group, an unsubstituted or substituted phenyl group G ^21, which is substituted by unsubstituted or G ²¹ A phenoxy group, an unsubstituted or G ²¹ -substituted pyridyl group, an unsubstituted or G ²¹ -substituted pyridyloxy group, a halogeno group, or a C 1-2 haloalkylenedioxy group.
The substituent G ²¹ is as described above, and is preferably a halogeno group, a C 1-6 haloalkyl group, or a C 1-6 haloalkoxy group.

Among these, Ar ² is preferably an unsubstituted or G ² -substituted C 6-10 aryl group (preferably a phenyl group), an unsubstituted or G ² -substituted C 6-10 aryloxy group ( preferably a phenoxy group), an unsubstituted or 3-10 membered heterocyclyl group (preferably a thiazolyl group which is substituted by G ^2, triazolyl group, a pyrazolyl group, a pyridyl group, pyridazinyl group, quinolyl group), unsubstituted or G ² 3 to 10-membered heterocyclyloxy group (preferably pyridyloxy group, pyrazinyloxy group, pyrimidinyloxy group).
As the ^{G 2,} Cl to 6 haloalkyl group, Cl to 6 haloalkoxy group, a halogeno group is more preferable.

<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 C1~C6 alkyleneoxy C1~6 alkylene group substituted with G ^4, unsubstituted or C3~C6 cycloalkylene group substituted by G ^4, which is substituted unsubstituted or at G ⁴ C1~C6 alkylene C3~6 cycloalkylene group, an unsubstituted or substituted by G ⁴ a C1~C6 alkyleneoxy C3~6 cycloalkylene group, an unsubstituted or C4~C6 cycloalkenylene group substituted with G ^4, Or a 3-6 membered heterocyclylene group which is unsubstituted or substituted with G ⁴ .
In B ^a, C1 -C6 alkylene groups are those as already mentioned.
The C2-C6 alkenylene group is a divalent group formed by removing two hydrogen atoms from the C2-C6 alkene. Examples of the C2-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-C6 alkynylene group include an ethynylene group, a propynylene group, and a butynylene group.
The C1-C6 alkyleneoxy C1-6 alkylene group is a group formed by bonding two C1-6 alkylene groups via an oxygen atom. Examples of the C1-C6 alkyleneoxy C1-6 alkylene group include a methyleneoxymethylene group, a methyleneoxyethylene group, and an ethyleneoxymethylene group.

A C3-C6 cycloalkylene group is a divalent group formed by removing two hydrogen atoms from a C3-C6 cycloalkane. Examples of the C3-C6 cycloalkylene group include a cyclopropylene group (1,2-cyclopropylene group), a cyclobutylene group (1,2-cyclobutylene group, or 1,3-cyclopentylene 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 C1-C6 alkylene C3-6 cycloalkylene group is a group formed by bonding a C1-6 alkylene group and a C3-6 cycloalkylene group.
The C1-C6 alkylene C3-6 cycloalkylene group is preferably a C1-2 alkylene C3-6 cycloalkylene group such as methylenecyclopropylene, methyleneoxycyclohexylene, ethyleneoxycyclohexylene.
The C1-C6 alkyleneoxy C3-6 cycloalkylene group is a group formed by bonding a C1-6 alkylene group and a C3-6 cycloalkylene group via an oxygen atom.
The C1-C6 alkyleneoxy C3-6 cycloalkylene group is preferably a C1-2 alkyleneoxy C3-6 cycloalkylene group such as methyleneoxycyclopropylene, methyleneoxycyclohexylene, ethyleneoxycyclohexylene.

  A C4-C6 cycloalkenylene group is a divalent group formed by removing two hydrogen atoms from a C3-C6 cycloalkene. Examples of the C4-C6 cycloalkenylene group include a cyclobutenylene group (1,2-cyclobutenylene group, 1,3-cyclobutenylene group, 1,3-cyclobutenylene group, or 3,4-cyclobutenylene group), a cyclopentenylene group (1, 2-cyclopentenylene group, 1,3-cyclopentenylene group, 1,4-cyclopentenylene group or 1,5-cyclopentenylene group), cyclohexenylene group (1,2-cyclohexene group) A senylene group, a 1,3-cyclohexenylene group, a 1,4-cyclohexenylene group, and the like, preferably a cyclopentenylene group or a cyclohexenylene group.

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 ring constituent atoms.
Examples of the 3-6 membered heterocyclylene group include a 3-6 membered saturated heterocyclylene group or a 5-6 membered partially unsaturated heterocyclylene group.
Examples of the 3- to 6-membered heterocyclylene group include dihydrofurylene group, tetrahydrofurylene group, pyrrolinylene group, pyrrolidinylene group, pyrazolinylene group, pyrazolidinylene group, imidazolinylene group, imidazolidinylene group, oxazolinylene group, oxazolidinylene group, Examples include 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 3-6 membered heterocyclylene group, a 5-6 membered saturated heterocyclylene group is preferable, and a piperidinylene group is particularly preferable.
In certain embodiments, the 3-6 membered heterocyclylene group is a C1-6 alkylene group and may be crosslinked.

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 substituents It has been C2~C6 alkynylene group, or an unsubstituted or C3~C6 cycloalkylene group substituted with G ⁴ or unsubstituted or 3-6 membered heterocyclylene group substituted by G ^4,, more preferably , an unsubstituted or C1~C6 alkylene group substituted with G ^4, unsubstituted or C3~C6 cycloalkylene group substituted with G ^4.

G ⁴ are, Cl to 6 alkyl, C3-8 cycloalkyl, Cl to 6 haloalkyl, Cl to 6 alkoxy Cl to 6 alkyl groups, C2-6 alkenyloxy Cl to 6 alkyl groups, hydroxyl, Cl to 6 alkoxy group, Cl to 6 alkoxy Cl to 6 alkoxy, C2-6 alkenyloxy group, substituted with Cl to 6 alkoxy carbonyl group, an unsubstituted or C6~10 aryl groups substituted with G ^21, unsubstituted or G ²¹ been 3-6 membered heterocyclyl group, a cyano group, a halogeno group, Cl to 6 alkylene groups, Cl to 6 alkylenedioxy group, an oxo group, C3-8 cycloalkyl Cl to 6 alkyl groups, unsubstituted or with G ²¹ substituted C6~10 aryl C1~6 alkyl, 3-6 membered heterocyclyl C1~6 alkyl substituted with unsubstituted or G ²¹ Group, C3-8 cycloalkyloxy C1~6 alkyl group, an unsubstituted or C6~10 aryloxy C1~6 alkyl group substituted with G ^21, unsubstituted or 3-6 membered heterocyclyl optionally substituted with G ²¹ oxy Cl to 6 alkyl groups, Cl to 6 alkylidene group, Cl to 6 alkoxyimino group, the unsubstituted or C6~10 aryl Cl to 6 alkoxyimino group substituted with G ²¹ or Cl to 6 alkyl hydrazino group, Show.

In G ^4, Cl to 6 alkyl, C3-8 cycloalkyl, Cl to 6 haloalkyl, Cl to 6 alkoxy Cl to 6 alkyl, Cl to 6 alkoxy, Cl to 6 alkoxy Cl to 6 alkoxy groups, C1 -6 alkoxycarbonyl group, C1-6 alkylenedioxy group, C6-10 aryl group, C6-10 aryl C1-6 alkyl group, 3-6 membered heterocyclyl group, 3-6 membered heterocyclyl C1-6 alkyl group, halogeno group , C1-6 alkylene group, substituent G ² and substituent G ²¹ are as described above.

A C2-6 alkenyloxy group is a hydroxyl group substituted by a C2-6 alkenyl group. Examples of the C2-6 alkenyloxy group include a vinyloxy group, a 1-propenyloxy group, a 2-propenyloxy group (allyloxy group), and the like.
The C2-6 alkenyloxy C1-6 alkyl group is a C1-6 alkyl group substituted with a C2-6 alkenyloxy group. Examples of the C2-6 alkenyloxy C1-6 alkyl group include a vinyloxymethyl group and an allyloxymethyl group.
Examples of the C3-8 cycloalkyl C1-6 alkyl group include a cyclopropylmethyl group and a cyclopentylmethyl group.

Examples of the C3-8 cycloalkyloxy C1-6 alkyl group include a cyclopropyloxymethyl group and a cyclohexyloxymethyl group.
Examples of the C6-10 aryloxy C1-6 alkyl group include a phenoxymethyl group and a naphthyloxymethyl group.

Preferred examples of the 3-6 membered heterocyclyloxy C1-6 alkyl group include 5-6 membered heteroarylmethyl groups such as a pyrazolyloxymethyl group and a pyridyloxymethyl group.
Examples of the C1-6 alkylidene group include a methylidene group and a propane-2-ylidene group.
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 =).

The ^{G 4} Of these, Cl to 6 alkyl, Cl to 6 haloalkyl, Cl to 6 alkoxy Cl to 6 alkyl groups, C2-6 alkenyloxy Cl to 6 alkyl groups, hydroxyl, Cl to 6 alkoxy groups, C1 6 alkoxycarbonyl, unsubstituted or C6~10 aryl groups substituted with G ²¹ (preferably a phenyl group), an unsubstituted or 3-6 membered heterocyclyl group which is substituted by G ²¹ (preferably a pyridyl group, pyrimidinyl group, dioxolanyl group), a halogeno group, Cl to 6 alkylene groups, Cl to 6 alkylenedioxy group, an oxo group, an unsubstituted or C6~10 aryl Cl to 6 alkyl group (preferably benzyl substituted by G ²¹ group), an unsubstituted or 3-6 membered heterocyclyl C1~6 alkyl group substituted with G ²¹ (preferably pyridinium Jirumechiru group, pyrazolyl methyl group, triazolylmethyl group), an unsubstituted or C6~10 aryloxy C1~6 alkyl group substituted with G ²¹ (preferably phenoxymethyl group), substituted with unsubstituted or G ²¹ The 3- to 6-membered heterocyclyloxy C1-6 alkyl group (preferably pyrazolyloxymethyl group), C1-6 alkylidene group, and C1-6 alkoxyimino group are preferred.

The substituent G ²¹ in G ⁴ is preferably a C 1-6 haloalkyl group, a C 1-6 haloalkoxy group, or a halogeno group.

Part of a substituent G ⁴ carbon atoms or B ^a of B ^a may form a 5- or 6-membered ring with the carbon atom on Ar ^2. Examples of the 5- to 6-membered ring include a cyclopentene ring, a cyclohexene ring, a dihydrofuran ring, a dihydrodioxin ring, a dihydropyran ring, and the like, and preferably a cyclopentene ring, a cyclohexene ring, a dihydrodioxin ring, and a dihydropyran ring. .

  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 according to the present invention yields the tautomeric pyridine-4-one compound shown below. 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.

[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.

  Agricultural and horticultural fungicides of the present invention include a wide variety of filamentous fungi, such as algae (Oomycetes), Ascomycetes, incomplete fungi (Deuteromycetes), basidiomycetes, mating It can be used for controlling plant diseases derived from fungi belonging to fungi (Zygomycetes).

Examples of plant diseases and pathogens to be controlled are shown below.
Sugar beet: brown spot disease (Cercospora beticola), black root disease (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc. ), Rust disease (Puccinia arachidis), withering disease (Pythium debaryanum), rust spot disease (Alternaria alternata), white silk disease (Sclerotium rolfsii) black astringency (Mycosphaerella berkeleyi), cucumber: powdery mildew (Sphaerotheca fuliginea), Downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), mycorrhizal disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea), anthracnose disease (Colletotrichum orbiculare), black star disease (Cladosporium cucumerinum), brown spot disease (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani Kuhn), homopsis root rot (Phomopsis sp.) Spot bacterial disease (Pseudomonas syringa) e pv. Lecrymans) Tomato: Gray mold disease (Botrytis cinerea), leaf mold disease (Cladosporium fulvum), plague (Phytophthora infestans), half body wilt disease (Verticillium albo-atrum), powdery mildew (Oidium neolycopersici), ring crest Diseases (Alternaria solani), Subtilis (Pseudocercospora fuligena), etc. Eggplant: Gray mold (Botrytis cinerea), Black blight (Corynespora melongenae), Powdery mildew (Erysiphe cichoracearum), Subtilis (Mycovellosiella nattrassii), Mycovellosiella nattrassii Strawberries: Botrytis cinerea, powdery mildew (Sohaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), plague (Phytophthora cactorum), soft rot (Rhizopus stoifer) (Fusarium oxysporum) Onions: gray rot (Botrytis allii), gray mold (Botrytis cinerea), white leaf blight (Botrytis squamosa), downy mildew (Peronospora d estructor), white plague (Phytophthora porri), etc. cabbage: root-knot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), black rot disease (Xanthomonas campesrtis pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicalas, Pseudomonas syringae pv. alisalensis), downy mildew (Peronospora parasitica), mycorrhizal disease (Sclerotinia sclerotiorum), black soot disease (Alternaria brassicicola), gray mold disease (Botrytis cinerea), etc. Kidney: Sclerotinia sclerotiorum, gray mold Diseases (Botrytis cinerea), anthrax (Colletotrichum lindemuthianum), keratosis (Phaeoisariopsis griseola), 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), gray mold disease (Botrytis cinerea), etc. Ume: black rot (Cladosporium carpophilum), gray mold disease (Botrytis cinerea), gray star disease (Monilinia mumecola), etc. Oysters: powdery mildew (Phyllactinia kakicola), anthrax Diseases such as Gloeosporium kaki, Cercospora kaki, peaches: Monilinia fructicola, black scab (Cladosporium carpophilum), homopsis spoilage (Phomopsis sp.), Perforated bacteria (Xanthomonas campestris pv. Pruni) and other almonds: Monilinia laxa, spot disease (Stigmina carpophila), black spot disease (Cladosporium carpophilum), leaf blight disease (Polystigma rubrum), spotted leaf disease (Alternaria alternata), anthrax Sugar beetle (Colletotrichum gloeospoides), etc. Sweet potato: Monilinia fructicola, anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Larvae nuclear disease (Monilinia kusanoi), etc. Grapes: Gray mold disease (Botrytis) cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black mildew (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot ( Guignardia bidwellii), white rot (Coniella castaneicola), etc. Pear: Venturia nashicola, Red Star Disease (Gymnosporangium asiaticum), Black Spot Disease (Alternaria kikuchiana), Ring Ring Disease (Botryosphaeria berengeriana) Powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown spot disease (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Cha: Ring-to-leaf disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis) ) Citrus, etc .: Scab (Elsinoe fawcetti), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), sunspot (Diaporthe citri), scab (Xanthomonas campestris pv.Citri) ), Powdery mildew (Oidium sp.), 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) ), Ergot disease (Claviceps purpurea), pine scab (Tilletia caries), naked scab (Ustilago nuda), etc. Bare smut (Ustilago tritici, U.nuda), etc. Rice: Rice blast (Pyricularia oryzae), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicolum , White leaf blight (Xanthomonas oryzae), seedling blight (Burkholderia plantarii), brown streak (Acidovorax avenae), blight blight (Burkholderia glumae), streak blight (Cercospora oryzae), rice leaf blight (Ustilaginoidea) virens), brown rice (Alternaria alternata, Curvularia intermedia), belly black rice (Alternaria padwickii), red rice (Epicoccam purpurascenns), etc. Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), plague ), Etc. Tulip: Gray mold disease (Botrytis cinerea) Sunflower: Downy mildew (Plasmopara halstedii), Mycorrhizal disease (Sclerotinia sclerotiorum), etc. Bentgrass: Snow rot (Sclerotinia borealis), Large patch (Rhizoctonia solani) , Dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), Red blight (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola) Orchardgrass: powdery mildew (Erysiphe graminis), etc. Soybean: Purpura (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyrhizi), mycoses (Sclerotinia sclerotiorum) Anthracnose (Colletotrichum truncatum), gray mold (Botrytis cinerea), etc. Potato: Phytophthora infestans, summer plague (Aleternaria solani), black rot (Thanatephorus cucumeris), etc. Banana: Panama disease (Fusarium oxysporum), Shiga (Mycosphaerella fijiensis, Mycosphaerella musicola), etc. Rapeseed: Sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae), etc. Coffee: Rust (Hemileia vastatrix), Anthrax (Colletotrichum coffeanum) Brown eye disease (Cercospora coffeicola), etc. Sugar cane: Brown rust (Puccinia melanocephala), etc. Corn: Leopard disease Gloecercospora sorghi), rust disease (Puccinia sorghi), southern rust disease (Puccinia polysora), smut (Ustilago maydis), sesame leaf blight (Cochliobolus heterostrophus), soot rot (Setophaeria turcica), etc. Pythium sp), rust (Phakopsora gossypii), mildew (Mycosphaerella areola), anthrax (Glomerella gossypii), etc.

  The insecticide or acaricide of the present invention is excellent in controlling pests such as various agricultural pests and mites that affect the growth of plants. 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 diamondback moth, planthopper, leafhopper and aphids.

  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. Can be 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.

The agricultural and horticultural fungicide, pest control agent, and insecticidal or acaricidal fungicide for agricultural and horticultural use according to the present invention are other agricultural and horticultural effects having effects such as sterilization, insecticidal / miticidal, nematicidal, and soil-killing pests. Drugs for use; Plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. may be mixed or used together.
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 deaminase inhibitor: buprimate, 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 inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; ethaboxam;
(B) Cell division inhibitor: Penciclone;
(C) Delocalization inhibitor of spectrin-like protein: fluopicolide;

(3) Respiratory inhibitor:
(A) Complex I NADH oxidoreductase inhibitor: diflumetrim; tolfenpyrad;
(B) Complex II succinate dehydrogenase inhibitors: benodanyl, flutolanil, mepronil; isophetamide; fluopyram; fenfram, flumecyclox; , Furametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid;
(C) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin; 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: Andoprim, 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 signal transduction: fenpiclonil, fludioxonil; clozolimate, iprodione, procymidone, vinclozolin;

(6) Lipid and cell membrane synthesis inhibitors:
(A) Phospholipid biosynthesis, methyltransferase-inhibitors: edifenphos, iprobenphos, pyrazophos; isoprothiolane;
(B) lipid peroxidants: biphenyl, chloroneb, dichlorane, kinden, technazene, tolcrofosmethyl; etridiazole;
(C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbfocetylate, prothiocarb;
(D) Microorganisms that disturb the cell membrane of pathogenic bacteria: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(E) Agents that disrupt 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 inhibitor in C4-demethylation of sterol biosynthesis system: phenhexamide; fenpyrazamine;
(D) Sterol biosynthetic squalene epoxidase inhibitors: Pyributicarb; Naftifen, Terbinafine;

(8) Cell wall synthesis inhibition (a) Trehalase inhibitor: Validamycin;
(B) chitin synthase inhibitor: polyoxin, polyoxolim;
(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) , Mankappa, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; dichlorfluanide, tolylfluanid; guazatine, iminotadine acetate, iminoctadine albecate albesylate; anilazine; Quinomethionate; fluorimide;

(13) Other agents: DBEDC, fluorophorpet, guazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofuram, Agrobacterium, betoxazine, diphenylamine, methyl isothiocyanate (MITC ), Mildeomycin, Capsaicin, 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, amicarthiazole (Amicarthiazol), oxathia Piperoline (Oxathiapiprolin), methylam zinc, benazole, trichramide, uniconazole, mildeomycin, oxyfenthiin, picarbutrazox;

Insecticides, acaricides, nematicides, soil insecticides:
(1) Acetylcholinesterase inhibitor:
(A) Carbamate series: Alanicarb, Aldicarb, Bengiocarb, Benfuracarb, Butcarboxyme, Butoxycarboxyme, Carbaryl, Carbofuran, Carbosulfan, Ethiophenecarb, Fenobucarb, Formethanate, Furatiocarb, 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, fento , Folate, hosalon, phosmet, phosphamidone, phoxime, pyrimiphos-methyl, propenophos, propetamphos, prothiophos, pyracrofos, pyridafenthion, quinalphos, sulfotep, tebupyrine phos, temefos, terbufos, tetrachlorbinphos, thiomethone, triazophos, trichlorfos, bamidthione; Bromophos ethyl, BRP, carbophenothione, cyanophenphos, CYAP, dimethone-S-methylsulfone, diariphos, diclofenthion, dioxabenzophos, etrimphos, phensulfothione, flupyrazophos, phonophos, formothione, phosmethylan, isazophos, iodofenphos, Methacrifos, pyrimifos-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, bioareslin, 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) Homogeneous selective feeding inhibitors: flonicamid, pymetrozine, pyrifluquinazone;

(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. Kurstaki, 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 monosodium salt, thiocyclam;
(15) Chitin synthesis inhibitor: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, nobiflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron;
(16) Diptera molting disruptors: cyromazine;
(17) Molting hormone receptor agonists: Chromafenozide, halofenozide, methoxyphenozide, tebufenozide;
(18) Octopamine receptor agonist: Amitraz, demiditraz, chlordimeform;
(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, cyflumetofene, pivlumide;
(25) Ryanodine receptor modulator: chlorantraniliprole, cyantraniprole, fulvendiamide, cyclaniliprol, tetraniliprol;
(26) Mixed function oxidase inhibitor compound: piperonyl butoxide;
(27) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
(28) Other agents (unknown mechanism of action): azadirachtin, benzoximate, biphenazate, bromopropyrate, quinomethionate, cryolite, dicofol, pyridalyl; bencrothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP , Phenisobromolate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, fluphenazine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, tetrasul, trialacene; afidopyropen), flometokin, flufiprole, fluenesulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, me Luneodecanamide; fluralanel, afoxolanel, floxamethamide, 5- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -2- (1H-1,2, , 4-triazol-1-yl) benzonitrile (CAS: 943137-49-3), brofuranilide, 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. For example, dosage forms such as wettable powder, emulsion, aqueous solvent, granular wettable powder, powder, tablet and the like can be mentioned. 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.

  Some formulation examples are given. In addition, the formulation shown below is only an example, and can be modified within the scope of the gist of the present invention.

(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 was uniformly mixed and finely pulverized to obtain a wettable powder with 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 components 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 The above is mixed and wet milled until the particle size is 3 microns or less, A suspension with 10% active ingredient is obtained.

Example Next, an Example is shown and this invention is demonstrated more concretely. However, the present invention is not limited by the following examples.

Example 1
1- (4-Acetoxy-2,5,6-trimethylpyridin-3-yl) ethanone Preparation of O- (4-trifluoromethylbenzyl) oxime

(Process 1)
Synthesis of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone

A mixture of 3.2 g of 4-amino-3-penten-2-one and 10.0 g of 2,2,5,6-tetramethyl-4H-1,3-dioxin-4-one was added at 120 to 130 ° C. Stir for 5 hours. Thereafter, the reaction solution was cooled to room temperature, and diethyl ether was added to precipitate crystals. The crystals were separated by filtration to obtain the target compound. The yield was 38%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 1.99 (3H, s), 2.29 (3H, s), 2.34 (3H, s), 2.58 (3H, s), 10.42 (1H, br.s)

(Process 2)
Synthesis of tert-butyl N-{(4-trifluoromethylbenzyl) oxy} carbamate

4-trifluoromethylbenzyl bromide (1.5 g) was dissolved in acetonitrile (20 ml). To this solution, 1.2 g of tert-butyl N-hydroxycarbamate and 1.7 g of 1,8-diazabicyclo [5.4.0] -undec-7-ene were added and stirred at room temperature for 1 hour. Thereafter, the reaction solution was poured into 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution, then with 10% aqueous sodium hydroxide solution and finally dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 2.28 g of the objective compound. The yield was 100%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 1.48 (9H, s), 4.91 (2H, s), 7.15 (1H, br.s), 7.51 (2H, d), 7.63 (2H, d)

(Process 3)
Synthesis of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone O- (4-trifluoromethylbenzyl) oxime

0.65 g of tert-butyl N-{(4-trifluoromethylbenzyl) oxy} carbamate was dissolved in 15 ml of 1,2-dichloroethane. To this solution were added 0.30 g of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) -ethanone and 1 ml of trifluoroacetic acid, and the mixture was stirred at 50 to 60 ° C. for 1 hour. Thereafter, the reaction solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with ethyl acetate to obtain 0.20 g of the target compound. The yield was 34%.
The physical properties of the target compound were as follows.
¹ H-NMR (DMSO-d ₆ , δppm) 1.78 (3H, s), 1.96 (3H, s), 2.00 (3H, s), 2.17 (3H, s), 5.16 (2H, s), 7.56 (2H , d), 7.71 (2H, d), 10.92 (1H, br.s)

(Process 4)
Synthesis of 1- (4-acetoxy-2,5,6-trimethylpyridin-3-yl) ethanone O- (4-trifluoromethylbenzyl) oxime

0.16 g of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone O- (4-trifluoromethylbenzyl) oxime was dissolved in 10 ml of chloroform. To this solution, 45 mg of pyridine and 43 mg of acetyl chloride were added and stirred overnight at room temperature. Thereafter, the reaction solution was diluted with chloroform, washed with 1N hydrochloric acid, then with saturated aqueous sodium hydrogen carbonate, and finally dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 0.19 g of the objective compound. The yield was 100%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.03 (3H, s), 2.07 (3H, s), 2.11 (3H, s), 2.37 (3H, s), 2.50 (3H, s), 5.22 (2H, s ), 7.49 (2H, d), 7.62 (2H, d)

(Example 2)
1- (4-Acetoxy-2,5,6-trimethylpyridin-3-yl) ethanone Preparation of O- {2- (4-trifluoromethylphenyl) ethyl} oxime

(Process 1)
Synthesis of N- {2- (4-trifluoromethylphenyl) ethoxy} phthalimide

1.0 g of 4-trifluoromethylphenethyl alcohol and 1.28 g of N-hydroxyphthalimide were dissolved in 12 ml of tetrahydrofuran. To this solution, 2.07 g of triphenylphosphine was added. To this solution, 3.43 g of a 40% toluene solution of azodicarboxylic acid diethyl ester was added dropwise under ice cooling. The reaction was warmed to room temperature and stirred overnight. Thereafter, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 4/1 (volume ratio)) to obtain 1.94 g of the objective compound. The yield was 100%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 3.21 (2H, t), 4.47 (2H, t), 7.45 (2H, d), 7.56 (2H, d), 7.72-7.78 (2H, m), 7.80-7.86 (2H, m)

(Process 2)
Synthesis of O- {2- (4-trifluoromethylphenyl) ethyl} hydroxylamine

1.44 g of N- {2- (4-trifluoromethylphenyl) ethoxy} phthalimide was dissolved in 20 ml of dichloromethane. The solution was cooled to 0 ° C. and 0.22 g of methyl hydrazine was added dropwise. The reaction was stirred at 0 ° C. for 1.5 hours. Thereafter, diethyl ether was added, and insoluble matters were filtered off. The solvent was distilled off under reduced pressure to obtain 0.83 g of the target compound. The yield was 94%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.96 (2H, t), 3.90 (2H, t), 5.43 (2H, br.s), 7.33 (2H, d), 7.55 (2H, d)

(Process 3)
Synthesis of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone O- {2- (4-trifluoromethylphenyl) ethyl} oxime

0.83 g of O- {2- (4-trifluoromethylphenyl) ethyl} hydroxylamine was dissolved in 10 ml of 1,2-dichloroethane. To this solution, 0.50 g of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone and 1 ml of trifluoroacetic acid were added and stirred overnight at room temperature. Thereafter, 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 washed with diethyl ether to obtain 0.68 g of the target compound. The yield was 67%.
The physical properties of the target compound were as follows.
¹ H-NMR (DMSO-d ₆ , δppm) 1.79 (3H, s), 1.88 (3H, s), 2.11 (3H, s), 2.19 (3H, s), 3.00 (2H, t), 4.23 (2H , t), 7.49 (2H, d), 7.64 (2H, d), 10.96 (1H, br.s)

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

0.48 g of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone O- {2- (4-trifluoromethylphenyl) ethyl} oxime was dissolved in 10 ml of dichloromethane. To this solution, 0.19 g of triethylamine and 0.13 g of acetyl chloride were added and stirred overnight at room temperature. Thereafter, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.38 g of the objective compound. The yield was 72%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.04 (3H, s), 2.06 (3H, s), 2.21 (3H, s), 2.44 (3H, s), 2.51 (3H, s), 3.06 (2H, t ), 4.36 (2H, t), 7.35 (2H, d), 7.56 (2H, d)

(Example 3)
1- (4-Acetoxy-2,5,6-trimethylpyridin-3-yl) ethanone Preparation of O- (4-trifluoromethylphenyl) oxime

(Process 1)
Synthesis of tert-butyl N- (4-trifluoromethylphenoxy) carbamate

2.0 g of 4-fluorobenzotrifluoride was dissolved in 24 ml of dimethyl sulfoxide. To this solution, 1.95 g of tert-butyl N-hydroxycarbamate and 1.05 g of potassium hydroxide were added, and the mixture was stirred overnight at room temperature. Thereafter, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and finally 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 = 4/1 (volume ratio)) to obtain 1.5 g of the target compound. The yield was 44%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 1.50 (9H, s), 7.19 (2H, d), 7.50 (1H, s), 7.56 (2H, d)

(Process 2)
Synthesis of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone O- (4-trifluoromethylphenyl) oxime

0.85 g of tert-butyl N- (4-trifluoromethylphenoxy) carbamate was dissolved in 10 ml of 1,2-dichloroethane. To this solution, 0.50 g of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) -ethanone and 1 ml of trifluoroacetic acid were added and stirred at 50 ° C. for 1 hour. Thereafter, the reaction solution was poured into saturated aqueous sodium hydrogen carbonate and extracted with chloroform. The organic layer was washed with saturated brine, and finally dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with diethyl ether to obtain 0.39 g of the target compound. The yield was 41%.
The physical properties of the target compound were as follows.
¹ H-NMR (DMSO-d ₆ , δppm) 1.83 (3H, s), 2.21 (3H, s), 2.22 (3H, s), 2.24 (3H, s), 7.32 (2H, d), 7.68 (2H , d), 11.14 (1H, br.s)

(Process 3)
Synthesis of 1- (4-acetoxy-2,5,6-trimethylpyridin-3-yl) ethanone O- (4-trifluoromethylphenyl) oxime

0.25 g of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone O- (4-trifluoromethylphenyl) oxime was dissolved in 8 ml of dichloromethane. To this solution were added 0.10 g of triethylamine and 70 mg of acetyl chloride, and the mixture was stirred overnight at room temperature. Thereafter, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.14 g of the objective compound. The yield was 49%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.10 (3H, s), 2.23 (3H, s), 2.32 (3H, s), 2.50 (3H, s), 2.55 (3H, s), 7.27 (2H, d ), 7.57 (2H, d)

Example 4
Preparation of 1- (4-acetoxy-2,5,6-trimethylpyridin-3-yl) carbaldehyde O- {2- (4-trifluoromethylphenyl) ethyl} oxime

(Process 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. The solution was heated to reflux overnight. Then, it cooled to room temperature. The precipitated crystals were filtered, washed with diethyl ether, and finally dried to obtain 24.2 g of the target compound. The yield was 33%.
The physical properties of the target compound were as follows.
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-methoxy-2,5,6-trimethylnicotinate

12.2 g of ethyl 4-hydroxy-2,5,6-trimethylnicotinate was dissolved in 120 ml of acetone. To this solution was added 21.0 g of cesium carbonate and then 10.0 g of methyl iodide, and the mixture 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, and finally dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 10.0 g of the target compound. The yield was 77%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 1.40 (3H, t), 2.17 (3H, s), 2.48 (6H, s), 3.86 (3H, s) 4.41 (2H, q)

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

2.8 g of lithium aluminum hydride was added to 300 ml of tetrahydrofuran. To this solution, 10.0 g of ethyl 4-methoxy-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 finally dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 7.9 g of the target compound. The yield was 97%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.18 (3H, s), 2.48 (3H, s), 2.56 (3H, s), 3.81 (3H, s), 4.72 (2H, s)

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

7.9 g of (4-methoxy-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. The filtrate was concentrated under reduced pressure to obtain 5.98 g of the target compound. The yield was 77%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.22 (3H, s), 2.53 (3H, s), 2.73 (3H, s), 3.87 (3H, s), 10.50 (1H, s)

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

3.0 g of 4-methoxy-2,5,6-trimethylpyridine-3-carbaldehyde was dissolved in 50 ml of dichloromethane. To this solution, 33 ml of 1N boron tribromide / dichloromethane solution was added dropwise under ice cooling. After completion of dropping, the mixture was stirred overnight at room temperature. Thereafter, the reaction solution was ice-cooled and neutralized by adding a 10% aqueous sodium hydrogen carbonate solution. The precipitated crystals were filtered and finally dried to obtain 0.9 g of the target compound. The yield was 33%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.18 (3H, s), 2.43 (3H, s), 2.53 (3H, s), 10.46 (1H, s)

(Step 6)
Synthesis of 4-hydroxy-2,5,6-trimethylpyridine-3-carbaldehyde O- {2- (4-trifluoromethylphenyl) ethyl} oxime

0.32 g of O- {2- (4-trifluoromethylphenyl) ethyl} hydroxylamine was dissolved in 10 ml of 1,2-dichloroethane. To this solution, 0.26 g of 4-hydroxy-2,5,6-trimethylpyridine-3-carbaldehyde and a few drops of trifluoroacetic acid were added and stirred overnight at room temperature. Thereafter, the reaction solution was poured into saturated aqueous sodium hydrogen carbonate and extracted with chloroform. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was washed with diethyl ether to obtain 0.42 g of the target compound. The yield was 76%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.15 (3H, s), 2.45 (3H, s), 2.51 (3H, s), 3.11 (2H, d), 4.42 (2H, d), 7.36 (2H, d ), 7.57 (2H, d), 8.47 (1H, s)

(Step 7)
Synthesis of 1- (4-acetoxy-2,5,6-trimethylpyridin-3-yl) carbaldehyde O- {2- (4-trifluoromethylphenyl) ethyl} oxime

0.42 g of 4-hydroxy-2,5,6-trimethylpyridine-3-carbaldehyde O- {2- (4-trifluoromethylphenyl) ethyl} oxime was dissolved in 20 ml of dichloromethane. To this solution was added 0.22 g of triethylamine. Next, 0.14 g of acetyl chloride was added under ice cooling, 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. The organic layer was then 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. The yield was 79%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 2.09 (3H, s), 2.33 (3H, s), 2.54 (3H, s), 2.61 (3H, s), 3.09 (2H, d), 4.39 (2H, d ), 7.35 (2H, d), 7.57 (2H, d), 8.17 (1H, s)

(Example 5)
Preparation of methyl [2,3,6-trimethyl-5-[[4- (4-trifluoromethoxy) phenyl] cyclohexoxy] -4-pyridyl] carbonate

(Process 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%
The physical properties of the target compound were as follows.
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%.
The physical properties of the target compound were as follows.
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 solution, 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 dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 11.3 g of the target compound. Yield 77%.
The physical properties of the target compound were as follows.
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 bicarbonate, 0.6 g of potassium bromide and 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%.
The physical properties of the target compound were as follows.
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)
1- (4-allyloxy-2-ethyl-5,6-dimethyl-3-pyridyl) -N- [2-[[3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1- Synthesis of methyl-propoxy] methanimine

0.5 g of 4-allyloxy-2-ethyl-5,6-dimethylpyridine-3-carbaldehyde was dissolved in 10 ml of dichloromethane. To this reaction solution, 0.8 g of O- [2-[[3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1-methyl-propyl] hydroxylamine and trifluoroacetic acid were cooled with ice. A few drops were added and stirred overnight at room temperature. The reaction solution was poured into saturated aqueous sodium bicarbonate 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 0.75 g of the target compound. Yield 68%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 1.19-1.43 (9H, m), 2.21 (3H, s), 2.52 (3H, s), 3.06 (2H, q), 4.33-4.42 (3H, m), 5.32 -5.43 (2H, m), 5.57-5.61 (1H, m), 6.01-6.11 (1H, m), 7.79-8.25 (3H, m)

(Step 6)
Of 3- [2-[[3-Chloro-5- (trifluoromethyl) -2-pyridyloxy] -1-methyl-propoxy] iminomethyl] -2-ethyl-5,6-dimethyl-pyridin-4-ol Composition

1- (4-allyloxy-2-ethyl-5,6-dimethyl-3-pyridyl) -N- [2-[[3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1- 0.5 g of methyl-propoxy] methanimine was dissolved in 10 ml of methanol. To this solution were added 0.012 g of tetrakistriphenylphosphine palladium and 0.28 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 0.4 g of the desired compound. Yield 87%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 1.17-1.41 (9H, m), 1.99 (3H, s), 2.22 (3H, s), 2.85 (2H, q), 4.33-4.42 (1H, m), 5.57 -5.61 (1H, m), 7.78-8.22 (3H, m)

(Step 7)
[3- [2-[[3-Chloro-5- (trifluoromethyl) -2-pyridyl] oxy-1-methyl-propoxy] iminomethyl] -2-ethyl-5,6-dimethyl-4-pyridyl] acetate Synthesis of

3- [2-[[3-Chloro-5- (trifluoromethyl) -2-pyridyloxy] -1-methyl-propoxy] iminomethyl] -2-ethyl-5,6-dimethyl-pyridin-4-ol 0 0.4 g was dissolved in 10 ml of chloroform. After adding 0.2 g of triethylamine to this solution, 0.16 g of acetyl chloride was added under ice cooling, and the mixture was stirred overnight at room temperature. The reaction solution was poured into saturated aqueous sodium bicarbonate 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 0.37 g of the objective compound. Yield 84%.
The physical properties of the target compound were as follows.
¹ H-NMR (CDCl ₃ , δppm) 1.19-1.43 (9H, m), 2.06 (3H, s), 2.30 (3H, s), 2.51 (3H, s), 2.86 (2H, q), 4.43-4.45 (1H, m), 5.59-5.62 (1H, m), 7.82-8.26 (3H, m)

The compounds produced by the same method as in the above examples are shown in Tables 1 to 10.
In addition, the physical property data of the compounds are described in the “Physical Properties” column. As the physical property data, the melting point (° C.) refractive index (n _D ) or its property was described.
In the column of “configuration”, “E” indicates that the double bond of imine in the compound is E configuration, “Z” indicates Z configuration, and “EZ” indicates that the compound is in both configurations. It shows that it is a mixture of these compounds.
In the table, Ph is a phenyl group, Me is a methyl group, Et is an ethyl group, ⁿ Pr is an n-propyl group, ⁱ Pr is an isopropyl group, ^c Pr is a cyclopropyl group, and ⁿ Bu is n. - butyl group, a ^t Bu group is t- butyl group, Py is a pyridyl group, Ac is an acetyl group, Bn is PMB benzyl denotes a para-methoxybenzyl group.

  Table 1 shows compounds represented by formula (I) in which Q is an organic group represented by formula (I) (compound represented by formula (I-1) shown below). Disclose.

Tables 2 to 6 are compounds represented by formula (I), wherein Q is an organic group represented by formula (II) (formula (I-2) shown below) Compound). Here, the compounds described in Tables 2 to 6 are compounds in which R ¹ , R ² and R ³ are methyl groups.
The carbon atom marked with * in the structural formula in “B ^a ” represents a carbon atom bonded to oxygen of the oxime (the same meaning is shown in the following tables). Furthermore, the carbon atom or nitrogen atom marked with ** in the structural formula of “B ^a ” represents a carbon atom or nitrogen atom bonded to “Ar ² ” (the same meaning is shown in the following tables).
Compound c-187 in Table 3 is N-oxide.

  Tables 7 to 8 show substituents in the compound represented by the formula (I-3).

  Table 9 shows substituents in the compound represented by the formula (I-4).

Table 11 shows the ¹ H-NMR data of some of the compounds described in Tables 1 to 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-1
An emulsion containing 5% active ingredient was prepared by dissolving 5 parts by mass of the compound of the present invention in 95 parts by mass of a dimethylformamide solution containing 1.5% of polyoxyethylene sorbitan monolaurate.
The emulsion was diluted with an aqueous solution containing 0.02% polyoxyethylene sorbitan monolaurate to obtain a chemical solution having a compound concentration of 100 ppm. Subsequently, the chemical solution was sprayed on wheat seedlings (variety “Chihoku”, 1.0 to 1.2 leaf stage) cultivated in an unglazed pot. Leaves were air dried. Thereafter, conidia of wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) were sprinkled off and inoculated in a greenhouse at 22 to 25 ° C. for 7 days (treatment). On the other hand, without spraying the medicinal solution, wheat seedlings were inoculated with wheat powdery mildew conidia and kept in a 22-25 ° C. greenhouse for 7 days (no treatment). The lesion appearance on the leaves was compared with the untreated plot. The control value was calculated.
Control value (%) = 100− {area where lesions appear (treatment) / area where lesions appear (no treatment)} × 100

  A wheat powdery mildew control test was conducted on the compounds shown in Table 12. All the compounds had a control value of 75% or more.

(Test Example 2) Wheat red rust prevention test-1
An emulsion was prepared in the same manner as in Test Example 1. The emulsion was diluted with an aqueous solution containing 0.02% polyoxyethylene sorbitan monolaurate to obtain a chemical solution having a compound concentration of 100 ppm. The chemical solution was sprayed on wheat seedlings (variety “Noribayashi No. 61”, 1.0-1.2 leaf stage) cultivated in an unglazed pot. Leaves were air dried. Thereafter, summer spores of wheat red rust fungus (Puccinia recondita) were shaken off and inoculated in a greenhouse at 22 to 25 ° C. for 10 days. In the same manner as in Test Example 1, the lesion appearance state on the leaf was compared with no treatment, and the control value was calculated.

  The compound shown in Table 13 was subjected to a wheat rust control test. All the compounds had a control value of 75% or more.

(Test Example 3) Wheat powdery mildew control test-2
The compound of the present invention (5.62 parts by mass), surfactant (4.49 parts by mass) and dimethylformamide (89.89 parts by mass) were mixed and dissolved to obtain an emulsion containing 5.62% active ingredient.
The above emulsion was diluted with water to an active ingredient of 125 ppm to obtain a chemical solution. The said chemical | medical solution was sprayed on the wheat seedling (variety "Chihoku", 1.0-1.2 leaf stage) cultivated with the unglazed pot. After air-drying the leaves, conidia of wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) were sprinkled off and inoculated in a 20-25 ° C greenhouse for 7 days. In the same manner as in Test Example 1, the lesion appearance state on the leaf was compared with no treatment, and the control value was calculated.

  Disease control tests were conducted on the compounds shown in Table 14. All the compounds showed a control value of 75% or more.

(Test Example 4) Wheat red rust control test-2
An emulsion was prepared in the same manner as in Test Example 3. The emulsion was diluted with water to an active ingredient of 125 ppm to obtain a chemical solution. The said chemical | medical solution was sprayed on the wheat seedling (variety "Noribayashi 61", 1.0-1.2 leaf stage) cultivated with the 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 20-25 ° C. for 10 days. In the same manner as in Test Example 1, the lesion appearance state on the leaf was compared with no treatment, and the control value was calculated.

The wheat red rust control test shown in Table 15 was conducted. All the compounds showed a 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 5) Efficacy Confirmation Test for Lotus japonicus 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 to prepare an emulsion of 5% active ingredient. Prepared.
The emulsion was diluted with water to obtain a drug having a compound concentration of 125 ppm. Cabbage leaves were immersed in the chemical for 30 seconds and then air-dried. Thereafter, cabbage leaves were placed in a petri dish with filter paper and 5 second-instar larvae were inoculated. A glass lid was placed and placed in a constant temperature and humidity room at a temperature of 25 ° C. and a humidity of 65%. The test was performed in duplicate.

  The compound shown in Table 16 was tested for efficacy against Spodoptera litura. All compounds had an insecticidal rate of 100%.

Test Example 6 Efficacy Confirmation Test for Cotton Aphid An emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm.
Cotton aphid adults were inoculated on the first true leaf of cucumber 10 days after germination sowed in a 3 inch pot. One day later, the adult worms were removed, and the drug solution was sprayed on the cucumbers where the larvae that were delivered were infested. It was placed in a constant temperature and humidity room at a temperature of 25 ° C. and a humidity of 65%, and after 5 days, the life of the aphids was examined and the insecticidal rate was calculated. The test was performed in duplicate.

  The compounds shown in Table 17 were tested for efficacy against cotton aphids. All compounds had an insecticidal rate of 100%.

(Test Example 7) Efficacy Confirmation Test for Spider Mite An emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. On the first true leaf of green beans that had been sown for 10 days after being sown in 3 inch pots, 10 adult females of the spider mite were inoculated. One day later, the chemical solution was sprayed. It was placed in a constant temperature and humidity room with a temperature of 25 ° C. and a humidity of 65%, and after 3 days, the life and death of the spider mite were examined, and the insecticidal rate was calculated. The test was performed in duplicate.

  The compounds shown in Table 18 were tested for efficacy against urticae. All compounds had an insecticidal rate of 100%.

(Test Example 8) Efficacy confirmation test against bean aphids An emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. Cowpeas were bred in 3-inch pots and seed aphid nymphs were inoculated on the primary leaves. The said chemical | medical solution was sprayed on the cowpea which a bean aphid larva parasitizes. The cowpea was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%, and the viability of the bean aphid was examined after 4 days. The test was performed in duplicate.

  The compounds shown in Table 19 were tested for efficacy against legume aphids. All compounds had an insecticidal rate of 80% or more.

(Test Example 9) Efficacy Confirmation Test for Kanzawa Spider Mite An emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. Kidney seedlings were bred in 3-inch pots, and 10 adult female Kanzawa spider mites were inoculated on the primary leaves. The said chemical | medical solution was sprayed on kidney seedlings. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%, and the life and death of adults were examined 10 days after the application.

  The compounds shown in Table 20 were tested for efficacy against Kanzawa spider mite. All compounds had an insecticidal rate of 90% 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. Therefore, the pyridine compound of the present invention is industrially useful.

Claims (4)

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

[In Formula (I),
R ¹ is hydrogen atom, an unsubstituted or C1~6 alkyl group substituted with G ^1, unsubstituted or C1~6 alkoxy group substituted with G ^1, which is substituted by unsubstituted or G ² C6 10 aryl group, an unsubstituted or 3-6 membered heterocyclyl group which is substituted by G ^2, a cyano group or a halogeno group.
R ² and R ³ are each independently a hydrogen atom, an unsubstituted or C1~6 alkyl group substituted with G ^1, unsubstituted or C3~8 cycloalkyl group substituted by G ^1, the unsubstituted or Cl to 6 alkoxy group substituted with G ^1, a formyl group, a formyloxy group, an unsubstituted or Cl to 6 alkyl group substituted with G ^1, which is substituted by unsubstituted or G ¹ Cl to 6 alkylcarbonyloxy group, an unsubstituted or C6~10 aryl groups substituted with G ^2, (unsubstituted or substituted with G ¹ a C1~6 alkoxyimino)-C1-6 alkyl group, a cyano group or a halogeno, Indicates a group.
Here, R ¹ and R ² may be combined to form a 5- to 6-membered ring together with the carbon atom to which R ¹ and R ² are bonded.
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 6 alkynyl group, substituted with unsubstituted or C3~8 cycloalkyl group substituted with G ^1, unsubstituted or C6~10 aryl C1~6 alkyl group substituted with G ^2, unsubstituted or G ² It has been 3-6 membered heterocyclyl group, an unsubstituted or 3-6 membered heterocyclyl group C1~6 alkyl group substituted with G ^2, a formyl group, an unsubstituted or C1~6 alkylcarbonyl group substituted by G ¹ , unsubstituted or C3~8 cycloalkylcarbonyl group substituted with G ^1, unsubstituted or C1~6 alkenylcarbonyl group substituted with G ^1, unsubstituted or with G ² is substituted And C6~10 aryl carbonyl group, an unsubstituted or C1~6 alkoxycarbonyl group substituted with G ^1, unsubstituted or C2~6 alkenyloxycarbonyl group substituted with G ^1, unsubstituted or with G ¹ substituted Cl to 6 alkylsulfonyl group, unsubstituted or Cl to 6 alkylaminocarbonyl group substituted with G ^1, unsubstituted or substituted with G ¹ a (Cl to 6 alkylthio) carbonyl group, the unsubstituted Or a C1-6 alkylamino (thiocarbonyl) group substituted by G ¹ or a group represented by the formula (IV).

Wherein (IV), G ^a are independently a hydrogen atom, an unsubstituted or C1~6 alkyl group substituted with G ^1, unsubstituted or C2~6 alkenyl group substituted with G ^1, no showing a substituted by a substituted or G ¹ a C2~6 alkynyl group, an unsubstituted or C3~8 cycloalkyl group substituted by G ¹ or unsubstituted or C6~10 aryl groups substituted with G ^2, .
Wherein (IV), 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, unsubstituted or G C2~6 alkynyl group substituted with ^1, unsubstituted or C3~8 cycloalkyl group substituted with G ^1, unsubstituted or C6~10 aryl groups substituted with G ² or unsubstituted or G, ² represents a 3-6 membered heterocyclyl group substituted with ² .
In the formula (IV), T represents an oxygen atom, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio) carbonyl group, a carbonyl (thio) group, a (thio) carbonyloxy group, an oxycarbonyl ( Thio) group or a divalent group represented by —O—C (═O) —N (G ^b ) —.
* Indicates the bonding position of the group represented by the formula (IV).
Q represents either an organic group represented by formula (II) or formula (III).

[In Formula (II) and Formula (III),
Ar ¹ represents an unsubstituted or C6~10 aryl groups substituted with 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 with G ^2, unsubstituted or C6-10 aryloxy group which is substituted by G ^2, substituted with unsubstituted or G ² C6-10 arylthio group, an unsubstituted or C6~10 arylsulfinyl group substituted by G ^2, unsubstituted or C6~10 arylsulfonyl group substituted with G ^2, substituted with unsubstituted or G ² 3 to 10 membered heterocyclyl group, an unsubstituted or 3-10 membered heterocyclyloxy group which is substituted by G ^2, unsubstituted or 3-10 membered heterocyclylthio group or a ferrocenyl group substituted with G ^2.
R ^a is a hydrogen atom, an unsubstituted or Cl to 6 alkyl group substituted with G ^1, unsubstituted or C3~8 cycloalkyl group substituted with G ^1, amino group, Cl to 6 alkylcarbonylamino group , or unsubstituted or showing a C6~10 aryl group substituted by G ^2.
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 C1~C6 alkyleneoxy C1~6 alkylene group substituted with G ^4, unsubstituted or C3~C6 cycloalkylene group substituted by G ^4, which is substituted unsubstituted or at G ⁴ C1~C6 alkylene C3~6 cycloalkylene group, an unsubstituted or substituted by G ⁴ a C1~C6 alkyleneoxy C3~6 cycloalkylene group, an unsubstituted or C4~C6 cycloalkenylene group substituted with G ^4, Or a 3-6 membered heterocyclylene group which is unsubstituted or substituted with G ⁴ .
Further, ^a carbon atom of B ^a or ^a part of the substituent G ⁴ on B ^a may be bonded to a carbon atom on Ar ² to form a 5- to 6-membered ring.
* Indicates the bonding position of the organic group represented by formula (II) or formula (III). ]
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 A group or a halogeno group. R ^1, R ^2, R ^3, when two or more of R ⁴ or R ^a is the radical which is substituted by G ^1, G ¹ according may be the same or different from each other .
G ² is a C 1-6 alkyl group, a hydroxy C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-8 cycloalkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy C 1-6 alkyl. Group, C1-6 alkoxy C1-6 haloalkyl group, C2-6 haloalkenyl group, C2-6 haloalkynyl group, hydroxyl group, C1-6 alkoxy group, C3-8 cycloalkyl C1-6 alkoxy group, C1-6 alkoxyC1 -6 alkoxy group, C1-6 haloalkoxy group, C1-6 haloalkoxy C1-6 haloalkoxy group, formyl group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, formyloxy group, C1-6 alkylcarbonyl Oxy group, C1-6 alkoxycarbonyloxy group, C1-6 alkoxycarbonyl Amino group, an unsubstituted or C6~10 aryl groups substituted with G ^21, unsubstituted or C6~10 aryl C1~6 alkyl group substituted with G ^21, which is substituted by unsubstituted or G ²¹ C6 10 aryloxy group, an unsubstituted or 3-6 membered heterocyclyl group which is substituted by G ^21, unsubstituted or 3-6 membered heterocyclyloxy group which is substituted by G ^21, Cl to 6 alkylthio group, Cl to 6 alkylsulfinyl groups, Cl to 6 alkylsulfonyl group, Cl to 6 haloalkylthio group, Cl to 6 haloalkylsulfinyl group, Cl to 6 haloalkylsulfonyl group, a pentafluorosulfanyl group, substituted with unsubstituted or G ²¹ C6-10 An arylthio group, an unsubstituted or a C6-10 arylsulfinyl group substituted with G ²¹ , unsubstituted or Shows C6~10 arylsulfonyl group substituted with G ^21, a nitro group, a cyano group, a halogeno group, Cl to 6 alkylene group, a Cl to 6 alkylenedioxy group or a Cl to 6 halo alkylenedioxy group. ^{R 1, R 2, R 3} , R 4, R a, if two or more of G ^4, Ar ¹ or Ar ² is said group substituted with G ^2, G ² according are mutually They may be the same or different.
G ²¹ represents a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, or a halogeno group. If more than one of G ² or G ⁴ is a said group substituted with G ^21, G ²¹ according may be the same or different from each other.
G ⁴ are, Cl to 6 alkyl, C3-8 cycloalkyl, Cl to 6 haloalkyl, Cl to 6 alkoxy Cl to 6 alkyl groups, C2-6 alkenyloxy Cl to 6 alkyl groups, hydroxyl, Cl to 6 alkoxy group, Cl to 6 alkoxy Cl to 6 alkoxy, C2-6 alkenyloxy group, substituted with Cl to 6 alkoxy carbonyl group, an unsubstituted or C6~10 aryl groups substituted with G ^21, unsubstituted or G ²¹ been 3-6 membered heterocyclyl group, a cyano group, a halogeno group, Cl to 6 alkylene groups, Cl to 6 alkylenedioxy group, an oxo group, C3-8 cycloalkyl Cl to 6 alkyl groups, unsubstituted or with G ²¹ substituted C6~10 aryl C1~6 alkyl, 3-6 membered heterocyclyl C1~6 alkyl substituted with unsubstituted or G ²¹ Group, C3-8 cycloalkyloxy C1~6 alkyl group, an unsubstituted or C6~10 aryloxy C1~6 alkyl group substituted with G ^21, unsubstituted or 3-6 membered heterocyclyl optionally substituted with G ²¹ oxy Cl to 6 alkyl groups, Cl to 6 alkylidene group, Cl to 6 alkoxyimino group, an unsubstituted or C6~10 aryl Cl to 6 alkoxyimino group substituted with G ^{2 1} or Cl to 6 alkyl hydrazino group, Indicates. ]   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 at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.   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.