JP6508540B2 - Pyridine compound and use thereof - Google Patents

Description

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

  In the cultivation of agricultural and horticultural crops, a large number of control agents have been proposed against crop diseases, but their use is limited by their inadequate control efficacy and the emergence of drug resistant pathogens. There are many cases where it is difficult to say that it is a sufficiently satisfactory control drug because it causes phytotoxicity and pollution to plants, or the toxicity to animals and fish and its environmental impact is large. Therefore, there is a strong demand for the emergence of drugs that can be used safely with few such drawbacks.

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

WO 2003/103667 A

  The object of the present invention is to provide novel pyridine compounds, as well as agricultural and horticultural fungicides, pest control agents and insecticides or acaricides.

  As a result of studying in order to solve the above-mentioned subject, it came to complete the present invention including the following modes.

[1] A compound represented by the formula (I) or a salt thereof.

[In the 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 And an aryl group of 10 to 10, a 3 to 6 membered heterocyclyl group which is unsubstituted or 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 a G ¹ substituted C1-6 alkoxy group, a formyl group, a formyloxy group, an unsubstituted or G ¹ substituted C1-6 alkylcarbonyl group, an unsubstituted or G ¹ substituted C1-6 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 each of R ¹ and R ² is 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ア ル キ ニ 6 alkynyl group, unsubstituted or G ¹ substituted C 3-8 cycloalkyl group, unsubstituted or G ² substituted C ⁶ to 10 aryl C ¹ 6 alkyl group, unsubstituted or substituted G ² 3 to 6 membered heterocyclyl group, unsubstituted or G ² substituted 3 to 6 membered heterocyclyl group C1-6 alkyl group, formyl group, unsubstituted or G ¹ substituted C1-6 alkyl carbonyl group , 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 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, ^The 3- to 6-membered heterocyclyl group substituted by ² is shown.

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 ( It represents a divalent group represented by a thio) group or -O-C (= O) -N ( ^Gb )-.
* Indicates the bonding position of the group represented by formula (IV).

  Q represents any one of the organic groups represented by Formula (II) or Formula (III).

[In the formula (II) and the 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 an unsubstituted or G ² substituted C ⁶ to 10 aryl group, an unsubstituted or G ² substituted C ⁶ to 10 aryloxy group, an unsubstituted or G ² substituted C ⁶ to 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 an unsubstituted or G ⁴ substituted C ^{1 to} C ⁶ alkylene group, an unsubstituted or G ⁴ substituted C ² to C 6 alkenylene group, an unsubstituted or G ⁴ substituted C ² to C 6 alkynylene 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 3 to 6 membered heterocyclylene group which is unsubstituted or substituted by G ⁴ .
In addition, ^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.
* Represents the bonding position of the organic group represented by Formula (II) or Formula (III). ]

G ¹ represents a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, a C1-6 alkoxycarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group, a cyano Group or a halogeno group is shown. 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, Cl to 6 alkyl group, hydroxyalkyl Cl to 6 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C3-8 cycloalkyl groups, Cl to 6 haloalkyl, Cl to 6 alkoxy Cl to 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 alkylcarbonyl Oxy group, C1-6 alkoxy carbonyloxy group, C1-6 alkoxy carbonyl 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 To 10 aryloxy group, an unsubstituted or G ²¹ -substituted 3- to 6-membered heterocyclyl group, an unsubstituted or G ²¹ -substituted 3- to 6-membered heterocyclyloxy group, a C 1-6 alkylthio group, C 1 to 6 Alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, pentafluorosulfanyl group, unsubstituted or C6-10 substituted with G ²¹ Arylthio group, unsubstituted or G ²¹ substituted C 6-10 arylsulfinyl group, 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 It may be the same or different.

G ²¹ represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 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 3 to 6 membered heterocyclyl group, cyano group, halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C3-8 cycloalkyl C1-6 alkyl group, unsubstituted or 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 C1-6 alkyl group, C1-6 alkylidene group, C1-6 alkoxy imino group, C6-10 aryl C1-6 alkoxy imino group which is unsubstituted or substituted by G2 ¹ , or C1-6 alkyl hydrazino group Indicates ]

[2] An agricultural and horticultural germicidal agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to the above [1] and a salt thereof.
[3] A pest control agent containing, as an active ingredient, at least one selected from the group consisting of the compound according to the above [1] and a salt thereof.
[4] An insecticidal or acaricidal agent comprising, as an active ingredient, at least one selected from the group consisting of the compounds according to the above [1] and salts thereof.

  The pyridine compound according to the present invention is a novel compound having the effects of pest control, sterilization, acaricide, insecticidal and the like, causing no adverse effects on plants, and having little toxicity to human and fish and environmental impact. . In particular, it exhibits excellent control effects 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 insecticidal or acaricidal agents.

  The pyridine compound according to the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as a 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 And -10 aryl group, 3- to 6-membered heterocyclyl group, cyano group or halogeno group is shown.
The C1-6 alkyl group may be linear, or may be branched as long as the carbon number is 3 or more. As a C1-6 alkyl group, a methyl group, an ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n And -hexyl, i-pentyl, neopentyl, 2-methylbutyl, 2,2-dimethylpropyl and i-hexyl can be mentioned.
As a C1-6 alkoxy group, a methoxy group, an 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 can be mentioned.

  As a C6-10 aryl group, a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, a tetralinyl group etc. can be mentioned.

  The 3- to 6-membered heterocyclyl group contains, as a constituent atom of the ring, 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is heterocyclyl, the remaining rings may be either saturated alicyclic, unsaturated alicyclic or aromatic rings. As a 3- to 6-membered heterocyclyl group, a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group and the like can be mentioned.

  As a 3- to 6-membered saturated heterocyclyl group, 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 group Groups can be mentioned.

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

The substituent G ¹ is a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, a C1-6 alkoxycarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group , A cyano group, or a halogeno group. 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.
As a C1-6 alkoxy C1-6 alkoxy group, a methoxy methoxy group, a methoxy ethoxy group, etc. can be mentioned.
Examples of the C1-6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, a t-butoxycarbonyl group and the like.
As a C1-6 alkyl carbonyloxy group, an acetyloxy group, a propionyloxy group, a butyryloxy group etc. can be mentioned.
Examples of the C1-6 alkoxycarbonyloxy group include methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group and the like. be able to.

Substituents G ² is, Cl to 6 alkyl group, hydroxyalkyl Cl to 6 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C3-8 cycloalkyl groups, Cl to 6 haloalkyl, Cl to 6 alkoxy C1~ 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 Alkyl carbonyloxy group, C1-6 alkoxy carbonyloxy group, C1-6 alkoxy carbon 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 To 10 aryloxy group, an unsubstituted or G ²¹ -substituted 3- to 6-membered heterocyclyl group, an unsubstituted or G ²¹ -substituted 3- to 6-membered heterocyclyloxy group, a C 1-6 alkylthio group, C 1 to 6 Alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, pentafluorosulfanyl group, unsubstituted or C6-10 substituted with G ²¹ Arylthio group, unsubstituted or G ²¹ substituted C 6-10 arylsulfinyl group, unsubstituted Or a C6-10 arylsulfonyl group substituted by G ²¹ , a nitro group, a cyano group, a halogeno group, a C1-6 alkylene group, a C1-6 alkylenedioxy group, or a C1-6 haloalkylenedioxy group.

In the substituents G ^2, Cl to 6 alkyl, Cl to 6 alkoxy, Cl to 6 alkoxy Cl to 6 alkoxy, Cl to 6 alkoxycarbonyl, Cl to 6 alkylcarbonyloxy group, Cl to 6 alkoxycarbonyloxy group , A C 6-10 aryl group, a 3 to 6 membered heterocyclyl group and a halogeno group are as described above.

As a hydroxy C1-C6 alkyl group, a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group etc. can be mentioned.
As a C2-6 alkenyl group, 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 And 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
As a C2-6 alkynyl group, 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.
As C3-8 cycloalkyl group, a cyclopropyl group, cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, 2-adamantyl group etc. can be mentioned.

The C1-6 alkoxy C1-6 alkyl group is obtained by substituting the above-mentioned C1-6 alkoxy group for the C1-6 alkyl group described above. As a C1-6 alkoxy C1-6 alkyl group, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i And-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group and the like can be mentioned.
The C3-8 cycloalkyl C1-6 alkoxy group is a group in which the above-mentioned C3-8 cycloalkyl group is substituted for the already mentioned C1-6 alkoxy group. Examples of the C3-8 cycloalkyl C1-6 alkoxy group include a cyclopropyl methoxy group, a cyclobutyl methoxy group, a cyclopentyl methoxy group, a cyclohexyl methoxy group, a 2- (cyclopropyl) -ethoxy group and the like.

  The C1-6 alkylcarbonyl group is a carbonyl group to which the above-mentioned C1-6 alkyl group is bonded. As a C1-6 alkyl carbonyl group, an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group etc. can be mentioned.

The C1-6 alkoxycarbonylamino group is an amino group substituted with the already mentioned C1-6 alkoxycarbonyl group. Examples of the C1-6 alkoxycarbonylamino group include methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group, n-butoxycarbonylamino group, t-butoxycarbonylamino group and the like. be able to.
The C6-10 aryl C1-6 alkyl group is obtained by substituting the above-mentioned C6-10 aryl group for the C1-6 alkyl group described above. 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 hydroxyl group substituted with the already mentioned C6-10 aryl group. As a C6-10 aryloxy group, a phenoxy group, a naphthoxy group, etc. can be mentioned.

The 3- to 6-membered heterocyclyloxy group is a hydroxyl group substituted with a 3- to 6-membered heterocyclyl group. As a 3- to 6-membered heterocyclyloxy group, a pyrazolyloxy group, a pyridyloxy group and the like can be mentioned. The 3- to 6-membered heterocyclyloxy group is preferably a 5- to 6-membered heterocyclyloxy group.
The C1-6 alkylthio group is a SH group substituted with a C1-6 alkyl group. Examples of the C1-6 alkylthio group include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, i-butylthio group and the like.
The C1-6 alkylsulfinyl group is a sulfinyl group to which a C1-6 alkyl group is bonded. As a C1-6 alkyl sulfinyl group, a methyl sulfinyl group, an ethyl sulfinyl group, t-butyl sulfinyl group etc. can be mentioned.
The C1-6 alkylsulfonyl group is a sulfonyl group in which a C1-6 alkyl group is bonded. As a C1-6 alkyl sulfonyl group, a methyl sulfonyl group, an ethyl sulfonyl group, t-butyl sulfonyl group etc. can be mentioned.
The C6-10 arylthio group is a SH group substituted with a C6-10 aryl group. As a C6-10 arylthio group, a phenylthio group, a naphthylthio group, etc. can be mentioned.
The C6-10 arylthio group is a sulfanyl group substituted with a C6-10 aryl group. As a C6-10 arylthio group, a phenylthio group, a naphthylthio group, etc. can be mentioned.
The C6-10 arylsulfinyl group is a sulfinyl group substituted with a C6-10 aryl group. Examples of the C6-10 arylsulfinyl group include phenylsulfinyl group and naphthylsulfinyl group.
The C.sub.6-10 arylsulfonyl group is a sulfonyl group substituted with a C.sub.6-10 aryl group. As C6-10 arylsulfonyl group, a phenylsulfonyl group, a naphthyl sulfonyl group, etc. can be mentioned.

As a C1-6 alkylene group, it is a bivalent group which two hydrogen atoms in C1-6 alkane remove | deviate. As a C1-6 alkylene group, a methylene group, ethylene group (dimethylene group), trimethylene group, tetramethylene group, propane-1, 2-diyl group (namely, propylene group) etc. can be mentioned.
The C1-6 alkylenedioxy group is a divalent group formed by replacing two hydrogen atoms in a C1-6 alkane with an oxy group. The C1~6 alkylenedioxy group, methylenedioxy group (-OCH ₂ O-), ethylenedioxy group (-OCH ₂ CH ₂ O-), and the like trimethylenedioxy group. The C6~10 aryl groups substituted with C1~6 alkylenedioxy group is G ^2, 2,3-dihydro - benzo [1,4] Jiokishiru group, benzo [1,3] such that exemplified dioxolyl group Can.

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 same as the C1-6 alkyl group, the C2-6 alkyl group described above. 6 alkenyl group, C2-6 alkynyl group, C1-6 alkoxy group, and C1-6 alkylenedioxy group substituted by 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, Examples thereof include 2,2-trifluoro-1-trifluoromethylethyl group, perfluorohexyl group, perchlorohexyl group, and 2,4,6-trichlorohexyl group.

Examples of the C 2-6 haloalkenyl group include a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group.
Examples of the C2-6 haloalkynyl group include a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, a 5-bromo-2-pentynyl group and the like.
As C1-6 haloalkoxy group, 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-hexafluoro-butoxy group, 1-bromo-1,1,2 And 2-tetrafluoroethoxy group.
The C1~6 halo alkylenedioxy group, difluoromethylene dioxy group (-OCF ₂ O-), tetrafluoroethylene dioxy group (-OCF ₂ CF ₂ O-) and the like. The C6~10 aryl groups substituted with C1~6 halo alkylenedioxy group is G ^2, 2,2,3,3-tetrafluoro-2,3-dihydro - benzo [1,4] Jiokishiru group, A 2, 2- difluoro- benzo [1, 3] dioxolyl group etc. can be mentioned.

The C1-6 alkoxy C1-6 haloalkyl group, the C1-6 haloalkoxy C1-6 haloalkoxy group, the C1-6 haloalkylthio group, the C1-6 haloalkylsulfinyl group, and the C1-6 haloalkyl sulfonyl group are as described above, C1 A halogeno group is substituted by -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.
Examples of the C1-6 alkoxy C1-6 haloalkyl group include difluoro (methoxy) methyl group, 1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl group and the like.
Examples of the C1-6 haloalkoxy C1-6 haloalkoxy group include a difluoro (methoxy) methoxy group and a 1,2,2-trifluoro-2- (trifluoromethoxy) ethoxy group.
A trifluoromethylthio group, a 2,2,2- trifluoroethylthio group etc. can be mentioned as a C1-6 haloalkylthio group.
As C1-6 haloalkyl sulfinyl group, a trifluoromethyl sulfinyl group, a 2,2,2- trifluoroethyl sulfinyl group etc. can be mentioned.
A trifluoromethyl sulfonyl group, a 2,2,2- trifluoroethyl sulfonyl group etc. can be mentioned as a C1-6 haloalkyl sulfonyl group.

The substituent G ²¹ represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, or a halogeno group. These are as already mentioned.
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, R 1 is a hydrogen atom, a C 1-6 alkyl group which is unsubstituted or substituted by G 1 (preferably unsubstituted), an alkoxy group which is unsubstituted or substituted by G 1 (preferably unsubstituted). , C6-10 aryl group (preferably phenyl group) substituted by unsubstituted or G2 (preferably C1-6 alkoxy group, C1-6 alkoxycarbonyloxy group), 6-membered unsubstituted or G2 substituted The ring is preferably a heteroaryl group (preferably an unsubstituted pyridyl group), a cyano group or a halogeno group, and more preferably an unsubstituted C1-6 alkyl group or a halogeno group.

[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 a G ¹ substituted C1-6 alkoxy group, a formyl group, a formyloxy group, an unsubstituted or G ¹ substituted C1-6 alkylcarbonyl group, an unsubstituted or G ¹ substituted C1-6 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.
C1-6 alkyl group, C3-8 cycloalkyl group, C1-6 alkoxy group, C1-6 alkyl carbonyl group, C1-6 alkyl carbonyloxy group, C6-10 aryl group, halogeno group in R ² and R ³ And the substituents G ¹ , G ² are as already mentioned.
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- to 6-membered ring with the carbon atom to which each of R ¹ and R ² is attached. Examples of the 5- to 6-membered ring include cyclopentene ring and 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, formyl group is 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) C1-6 alkyl group, unsubstituted or G ¹ substituted C1-6 alkoxy group (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 G ¹ substituted C1-6 alkoxyimino) -C1-6 alkyl group (preferably unsubstituted), halogeno group, cyano group or formyl group Preferably, a C1-6 alkyl group or a halogeno group which is unsubstituted or substituted by G1 (preferably a hydroxyl group, a halogeno group, a C1-6 alkoxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group) is preferable More preferable.

[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ア ル キ ニ 6 alkynyl group, unsubstituted or G ¹ substituted C 3-8 cycloalkyl group, unsubstituted or G ² substituted C ⁶ to 10 aryl C ¹ 6 alkyl group, unsubstituted or substituted G ² 3 to 6 membered heterocyclyl group, unsubstituted or G ² substituted 3 to 6 membered heterocyclyl C1-6 alkyl group, formyl group, unsubstituted or G ¹ substituted C1 to 6 alkyl carbonyl group, 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 G Cl to 6 alkyl amino (thiocarbonyl) substituted with ¹ group or a group represented by the formula (IV),.

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 in R ⁴ carbonyl group, Cl to 6 alkoxycarbonyl, Cl to 6 alkylsulfonyl group, a substituent G ¹ and substituent G ² is are those as already mentioned.

The 3- to 6-membered heterocyclyl C1-6 alkyl group is a C1-6 alkyl group substituted with a 3- to 6-membered heterocyclyl group. As a 3- to 6-membered heterocyclyl C1-6 alkyl group, preferably, 5- to 6-membered saturated heterocyclyl C1-6 alkyl such as tetrahydrofuranylmethyl group, tetrahydropyranylmethyl group, dioxolanylmethyl group, dioxanylmethyl group and the like And 5- to 6-membered heteroaryl C1-6 alkyl groups such as pyrazolylmethyl group and pyridylmethyl group.
The C3-8 cycloalkylcarbonyl group is a carbonyl group to which the aforementioned C3-8 cycloalkyl group is bonded. Examples of the C3-8 cycloalkylcarbonyl group include cyclopropylcarbonyl group, cyclobutylcarbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl group and the like.
The C6-10 arylcarbonyl group is a carbonyl group to which a C6-10 aryl group is bonded. A benzoyl group etc. can be mentioned as a C6-10 aryl carbonyl group.

An acryloyl group, a methacryloyl group, etc. can be mentioned as C2-6 alkenyl carbonyl group.
Examples of the C 2-6 alkenyloxycarbonyl group include vinyloxycarbonyl group, 1-propenyloxycarbonyl group, 2-propenyloxycarbonyl group (allyloxycarbonyl group) and the like.
Examples of the C1-6 alkylaminocarbonyl group include a methylaminocarbonyl group, a dimethylaminocarbonyl group and the like.
Examples of the (C1-6 alkylthio) carbonyl group include (methylthio) carbonyl group, (ethylthio) carbonyl group and the like.
Examples of the C1-6 alkylamino (thiocarbonyl) group include a methylamino (thiocarbonyl) group, a dimethylamino (thiocarbonyl) group and the like.

[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 To 6 alkynyl group, unsubstituted or G ¹ substituted C 3-8 cycloalkyl group, unsubstituted or G ² substituted C 6 10 aryl group, or unsubstituted or G ² substituted 3 Indicates a 6-membered heterocyclyl group.
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 formula : -O-C (= O) -N (G < ^b >)-.
* Indicates the bonding position of the group represented by formula (IV). ]

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

In the present invention, R ⁴ is C ^{1 to} C ⁶ substituted by a hydrogen atom, unsubstituted or G ¹ (preferably C ^{1 to} C ⁶ alkylcarbonyloxy group, C ^{1 to} C ⁶ alkoxycarbonyloxy group, halogeno group) alkyl group, an unsubstituted or C2~6 alkenyl group substituted with G ¹ (preferably unsubstituted), C6-10 aryl C1~ substituted with unsubstituted or G ² (preferably C1~6 alkoxy group) 6 alkyl group (preferably benzyl group), unsubstituted or C1-6 alkylcarbonyl group substituted with G ¹ (preferably C1-6 alkoxy group, C1-6 alkylcarbonyloxy group), unsubstituted or G ¹ And C 1-6 alkoxycarbonyl group (preferably unsubstituted) substituted with or C 2-6 alkenyl carbony which is unsubstituted or substituted by 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 Group (preferably, unsubstituted), heterocyclyl group (preferably, 3 to 6-membered saturated heterocyclyl group) which is unsubstituted or substituted by G ² (preferably, a hydroxyl group, a hydroxy C1-6 alkyl group) is preferable, and a hydrogen atom is preferable C1-6 alkyl group which is unsubstituted or substituted by G ¹ (preferably C1-6 alkylcarbonyloxy group, C1-6 alkoxycarbonyloxy group), unsubstituted or G ¹ (preferably 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 any one of the organic groups 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.
C1~6 alkyl group for R ^a, C3-8 cycloalkyl group, C6-10 aryl group, the substituents G ¹ and substituent G ² is are those as already mentioned.
The C1-6 alkylcarbonylamino group is obtained by substituting an amino group with the already mentioned C1-6 alkylcarbonyl group. As a C1-6 alkyl carbonylamino group, an acetylamino group, a propionylamino group, etc. can be mentioned.
In the present invention, as Ra, ^a hydrogen atom, an unsubstituted alkyl group, an unsubstituted C3-8 cycloalkyl group (preferably a C3-4 cycloalkyl group), an amino group, a C1-6 alkylcarbonylamino group C6~10 aryl group (preferably a phenyl group) is preferably substituted with unsubstituted or G ² (preferably C1~6 haloalkyl group), an alkyl group or a hydrogen atom unsubstituted is 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 nitrogen atoms, oxygen atoms and sulfur atoms 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 rings may be either saturated alicyclic, unsaturated alicyclic or aromatic rings. As a 3- to 10-membered heterocyclyl group, a 3- to 10-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group and the like can be mentioned.

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

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

As a 5- to 6-membered partially unsaturated heterocyclyl group,
5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group;
6-membered partially unsaturated heterocyclyl group such as isoxazolinyl group, 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 pyrazolyl group, pyridyl group, pyrimidinyl group and quinolinyl group.

In the present invention, Ar ¹ is unsubstituted or C6~10 aryl groups substituted with G ² (preferably a phenyl group, a naphthyl group) or unsubstituted or 5-6 membered heteroaryl substituted with G ² It is preferably a group (preferably pyridyl group), more preferably an unsubstituted or G ² -substituted phenyl group or an unsubstituted or G ² -substituted pyridyl group.
G ² in Ar ¹ is, Cl to 6 alkyl, Cl to 6 haloalkyl, Cl to 6 alkoxy, Cl to 6 alkoxy Cl to 6 haloalkyl, Cl to 6 haloalkoxy group, Cl to 6 alkoxycarbonyl group, no 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 C1-6 alkyl group (preferably benzyl group), C6-10 aryloxy group (preferably phenoxy group) unsubstituted or substituted with G ²¹ (preferably C1-6 haloalkyl group), C1-6 Haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, pentafu 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) C6-10 arylsulfinyl group (preferably phenylsulfinyl group) substituted by C6-10 arylsulfonyl group (preferably phenylsulfonyl group) which is unsubstituted or substituted by G ²¹ (preferably C1-6 haloalkyl group) Preferably a nitro group, a C1-6 haloalkylenedioxy group and / or a halogeno group,
More preferably, a C6-10 aryloxy group (preferably, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, unsubstituted or substituted with G ²¹ (preferably a C1-6 haloalkyl group) (preferably Is a phenoxy group) and / or a halogeno group.

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

Substituents G ² is is of as already mentioned, preferably, Cl to 6 alkyl, Cl to 6 haloalkyl, Cl to 6 alkoxy group, is C3~8 cycloalkyl Cl to 6 alkoxy group (preferably C3~ 4 cycloalkylalkoxy group), Cl to 6 haloalkoxy group, an unsubstituted or C6~10 aryl groups (preferably phenyl group substituted with G ^21), an unsubstituted or C6~10 aryl substituted with G ²¹ An oxy group (preferably a phenoxy group), an unsubstituted or G ²¹ -substituted 5- or 6-membered heterocyclyl group (preferably a pyridyl group), an unsubstituted or G ²¹ -substituted 5- or 6-membered heterocyclyloxy group Preferably, pyridyloxy group), pentafluorosulfanyl group, cyano group, halogeno group or C1-6 haloalkylene dioxy A group.
As G ² , more preferably, a C ^{1 to 6} haloalkyl group, a C 1 to 6 alkoxy group, a C 1 to 6 haloalkoxy group, an unsubstituted or substituted G ²¹ phenyl group, an unsubstituted or G ²¹ substituted phenoxy group shown, unsubstituted or pyridyl group substituted with G ^21, unsubstituted or pyridyloxy group substituted with G ^21, a halogeno group or C1~2 halo alkylenedioxy group.
The substituent G ²¹ is as described above, preferably a halogeno group, a C1-6 haloalkyl group or a C1-6 haloalkoxy group.

Among these, Ar ^2, preferably, unsubstituted or C6~10 aryl groups substituted with G ² (preferably a phenyl group), an unsubstituted or C6~10 aryloxy group substituted with G ² ( 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 A 3- to 10-membered heterocyclyloxy group (preferably a pyridyloxy group, a pyrazinyloxy group, a pyrimidinyloxy group) substituted by
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 an unsubstituted or G ⁴ substituted C ^{1 to} C ⁶ alkylene group, an unsubstituted or G ⁴ substituted C ² to C 6 alkenylene group, an unsubstituted or G ⁴ substituted C ² to C 6 alkynylene 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 3 to 6 membered heterocyclylene group which is unsubstituted or substituted by G ⁴ .
The C1-C6 alkylene group in B ^a is as described above.
The C2-C6 alkenylene group is a divalent group formed by removing two hydrogen atoms in a C2-C6 alkene. Examples of the C2 to C6 alkenylene group include an ethenylene group, a propenylene group and a butenylene group.
A C2-C6 alkynylene group is a divalent group formed by removing two hydrogen atoms in a C2-C6 alkyne. Examples of the C2-C6 alkynylene group include ethynylene group, propynylene group and butynylene group.
The C1 to C6 alkyleneoxy C1 to 6 alkylene group is a group formed by combining two C1 to 6 alkylene groups via an oxygen atom. As a C1-C6 alkylene oxy C1-6 alkylene group, a methylene oxy methylene group, a methylene oxy ethylene group, an ethylene oxy methylene group etc. can be mentioned.

The C3-C6 cycloalkylene group is a divalent group formed by removing two hydrogen atoms in a C3-C6 cycloalkane. As a C3 to C6 cycloalkylene group, a cyclopropylene group (1,2-cyclopropylene group), a cyclobutylene group (1,2-cyclobutylene group, or a 1,3-cyclopentylene group), a 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. And preferably a cyclopentylene group or a cyclohexylene group.
The C1 to C6 alkylene C3 to 6 cycloalkylene group is a group formed by combining a C1 to 6 alkylene group and a C3 to 6 cycloalkylene group.
As the C1 to C6 alkylene C3 to 6 cycloalkylene group, a C1 to 2 alkylene C3 to 6 cycloalkylene group such as methylenecyclopropylene, methyleneoxycyclohexylene, ethyleneoxycyclohexylene and the like is preferable.
The C1 to C6 alkyleneoxy C3 to 6 cycloalkylene group is a group formed by combining a C1 to 6 alkylene group and a C3 to 6 cycloalkylene group via an oxygen atom.
As a C1-C6 alkylene oxy C3-6 cycloalkylene group, C1-2 alkylene oxy C3-6 cycloalkylene groups, such as a methylene oxy cyclopropylene, a methylene oxy cyclohexylene, ethyleneoxy cyclohexylene, etc. are preferable.

  The C4 to C6 cycloalkenylene group is a divalent group formed by removing two hydrogen atoms in a C3 to C6 cycloalkene. As C 4 -C 6 cycloalkenylene group, cyclobutenylene group (1,2-cyclobutenylene group, 1,3-cyclobutenylene group, 1,3-cyclobutenylene group, or 3,4-cyclobutenylene group), cyclopentenylene group (1,1 2-cyclopentenylene group, 1,3-cyclopentenylene group, 1,4-cyclopentenylene group, or 1,5-cyclopentenylene group), cyclohexenylene group (1,2-cyclohexene group) Mention may be made of a enylene group, a 1,3-cyclohexenylene group, a 1,4-cyclohexenylene group, etc., and a cyclopentenylene group or a cyclohexenylene group is preferred.

The 3- to 6-membered heterocyclylene group is a divalent group formed by removing two hydrogen atoms in the heteroalicyclic compound. The heteroalicyclic compound is a non-aromatic compound containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as constituent atoms of the ring.
As a 3- to 6-membered heterocyclylene group, a 3- to 6-membered saturated heterocyclylene group or a 5- to 6-membered partially unsaturated heterocyclylene group can be mentioned.
As a 3- to 6-membered heterocyclylene group, a dihydrofurylene group, a tetrahydrofurylene group, a pyrrolinylene group, a pyrrolidinylene group, a pyrazolinylene group, a pyrazolidinylene group, an imidazolinylene group, an imidazolidinylene group, an oxazolylene group, an oxazolidinylene group Examples include thiazolylene group, thiazolidinylene group, isoxazolidinylene group, isothiazolidinylene group, dihydropyranylene group, tetrahydropyranylene group, piperidinylene group, piperazinylene group, morpholinylene group and the like.
Among these, as a 3- to 6-membered heterocyclylene group, a 5- to 6-membered saturated heterocyclylene group is preferable, and a piperidinylene group is particularly preferable.
In certain embodiments, 3- to 6-membered heterocyclylene groups may be bridged by C1-6 alkylene groups.

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 A C2 to C6 alkynylene group, an unsubstituted or G ⁴ substituted C ³ to C ⁶ cycloalkylene group, or an unsubstituted or G ⁴ substituted 3 to 6 membered heterocyclylene group, 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 3 to 6 membered heterocyclyl group, cyano group, halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C3-8 cycloalkyl C1-6 alkyl group, unsubstituted or 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 to 6 membered heterocyclyl group, 3 to 6 membered heterocyclyl C1-6 alkyl group, halogeno group The C1-6 alkylene group, the substituent G ² and the substituent G ²¹ are as described above.

The C2-6 alkenyloxy group is a hydroxyl group substituted with a C2-6 alkenyl group. As C2-6 alkenyloxy group, a vinyloxy group, 1-propenyl oxy group, 2-propenyl oxy group (allyloxy group) etc. can be mentioned.
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.
As C3-8 cycloalkyl C1-6 alkyl group, a cyclopropyl methyl group, a cyclopentyl methyl group, etc. can be mentioned.

As C3-8 cycloalkyl oxy C1-6 alkyl group, a cyclopropyl oxymethyl group, a cyclohexyl oxymethyl group, etc. can be mentioned.
As a C6-10 aryloxy C1-6 alkyl group, a phenoxymethyl group, a naphthyloxymethyl group, etc. can be mentioned.

As a 3- to 6-membered heterocyclyloxy C1-6 alkyl group, preferably, a 5- to 6-membered heteroarylmethyl group such as a pyrazolyloxymethyl group or a pyridyloxymethyl group can be mentioned.
Examples of the C1-6 alkylidene group include a methylidene group and a propan-2-ylidene group.
As a C1-6 alkoxy imino group, a methoxy imino group (MeO-N =), an ethoxy imino group (EtO-N =), etc. can be mentioned.
Examples of the C6-10 aryl C1-6 alkoxyimino group include a benzyloxyimino group (BnO-N =) and the like.
As a C1-6 alkyl hydrazino group, a methyl hydrazino group (MeNH-N =), an ethyl hydrazino group (EtNH-N =), etc. can be mentioned.

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 To 6 alkoxycarbonyl group, unsubstituted or G ²¹ -substituted C 6-10 aryl group (preferably phenyl group), unsubstituted or G ²¹ -substituted 3- to 6-membered heterocyclyl group (preferably pyridyl group), Pyrimidinyl group, dioxolanyl group), halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C6-10 aryl C1-6 alkyl group unsubstituted or substituted with G ²¹ (preferably benzyl) Group, 3 to 6 membered heterocyclyl C.sub.1-6 alkyl group (preferably pyri) which is unsubstituted or substituted by G ^21. 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 preferred 3- to 6-membered heterocyclyloxy C1-6 alkyl group (preferably pyrazolyloxymethyl group), C1-6 alkylidene group and C1-6 alkoxyimino group are preferred.

Substituent ^{G 21} in G ⁴ are preferably Cl to 6 haloalkyl group, Cl to 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 cyclopentene ring, cyclohexene ring, dihydrofuran ring, dihydrodioxin ring, dihydropyran ring and the like, preferably a cyclopentene ring, cyclohexene ring, dihydrodioxin ring, dihydropyran ring .

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

[Tautomers]
The pyridine compound according to the present invention gives the following tautomeric pyridine-4-one compounds when R ⁴ is a hydrogen atom. In the formulas, R ¹ , R ² , R ³ and Q each have the same meaning as defined in formula (I). In the present invention, the tautomer pyridin-4-one compounds are also included in the present invention.

[Stereoisomers]
In the present invention, compounds that are represented by the same structural formula but differ in the spatial arrangement of atoms or substituents in the structure, such as all optical isomers, diastereoisomers, geometric isomers, etc. The stereoisomers of are also included in the present invention. The stereoisomers may be single or in mixtures.

〔salt〕
The salt of compound (I) according to the present invention is not particularly limited as long as it is an agronomically 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, copper and the like And salts of transition metals such as ammonia, triethylamine, tributylamine, pyridine, and salts of organic bases such as hydrazine. The salt of compound (I) can be obtained from compound (I) by a known method.

[Agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides]
The agricultural and horticultural fungicides, pest control agents, and insecticidal or acaricidal agents of the present invention are effective at least one selected from compound (I) or a salt thereof (hereinafter sometimes referred to as "the present compound") It is contained as a component.

  The agricultural and horticultural fungicides of the present invention may be conjugated to a wide variety of filamentous fungi such as, for example, Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, It can be used to control plant diseases derived from fungi belonging to the fungus (Zygomycetes).

Examples of plant diseases and pathogens to be controlled are shown below.
Sugar beet: Brown spot (Cercospora beticola), black root disease (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc. ), Rust (Puccinia arachidis), damping-off (Pythium debaryanum), rust (Alternaria alternata), white scab (Sclerotium rolfsii), black affliction (Mycosphaerella berkeleyi) etc. Downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine blight (Fusarium oxysporum), sclerotis disease (Sclerotinia sclerotiorum), Botrytis cinerea, Anthracnose (Colletotrichum orbiculare), (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani Kuhn), homoposis root rot (Phomopsis sp.) Spotted blight (Pseudomonas syringa) e pv. Lecrymans etc. Tomato: Botrytis cinerea, Cladosporium fulvum, Phytophthora infestans, Verticillium albo-atrum, powdery mildew (Oidium neolycopersici), ring crest Diseases (Alternaria solani), sour mildew (Pseudocercospora fuligena), etc. Eggplant: Botrytis cinerea, Corynespora melongenae, powdery mildew (Erysiphe cichoracearum), mildew (Mycovellosiella nattrasci) Diseases (Sclerotinia sclerotiorum), etc. Strawberries: Botrytis cinerea, powdery mildew (Sohaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), plague (Phytophthoracactorum), soft rot (Rhizopulus) (Fusarium oxysporum, etc.) Onion: Gray rot (Botrytis allii), gray mold (Botrytis cinerea), mildew (Botrytis squamosa), downy mildew (Peronospora d) eruptor), white blight (Phytophthora porri), etc. Cabbage: Plasmodiophora brassicae, soft rot (Erwinia carotovora), black rot (Xanthomonas campes rt. pv. syringae pv. alisalensis), downy mildew (Peronospora parasitica), sclerotis disease (Sclerotinia sclerotiorum), black scab (Alternaria brassicicola), gray mold (Botrytis cinerea), etc. Beans: sclerotinia sclerotiorum, gray scab Disease (Botrytis cinerea), anthrax (Colletotrichum lindemuthianum), horny mildew (Phaeoisariopsis griseola), etc.

Apple: powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), Monilia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), scab (Valsa mali), spotted leaf diseases (Alternaria mali), red star disease (Gymnosporangium) yamadae), Botryosphaerus (Botryosphaeria berengeriana), Anthracnose (Glomerella cingulata, Colletotrichum acutatum), Brown Spot Disease (Diplocarpon mali), Soot Spot Disease (Zygophiala jamaicensis), Soot Spot Disease (Gloeodes pomigena), Purple Coat Leaf Disease (Helicobasidium mompa), gray mold (Botrytis cinerea), etc. Ume: scab (Cladosporium carpophilum), gray mold (Botrytis cinerea), scab (Monilinia mumecola), etc. oyster (Phyllactinia kakicola), anthracnose Disease (Gloeosporium kaki), scaly leaf disease (Cercospora kaki), etc. peach: Heliosis (Monilinia fructicola), scab (Cladosporium carpophilum), homoposis rot (Phomopsis sp.), Perforated bacteria Almonds (Xanthomonas campestris pv. Pruni), etc. Almond disease (Monilinia laxa), Spotted disease (Stigmina carpophila), Scab (Cladosporium carpophilum), Leaf blight (Polystigma rubrum), Spotted leaf blight (Alternaria alternata), Anthrax Disease (Colletotrichum gloeospoides), etc. Sweet cherry (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Juvenile mildew (Monilinia kusanoi), etc. Grape: Botrytis (Botrytis) cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmoparaviticola), mildew (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot ( Guignardia bidwellii), white rot (Coniella castaneicola) etc. Pear: scab disease (Venturia nashicola), red star disease (Gymnosporangium asiaticum), scab (Alternaria kikuchiana), ring disease (Botyosphaeria berengeriana) Powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown leaf blight (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: Botrytis (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis) And so on) citrus: scab (Elsinoe fawcetti), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), scab (Xanthomonas campestris pv. Citri) ), Powdery mildew (Oidium sp.), Etc.

Wheat: powdery mildew (Erysiphe graminis f. Sp. Tritici), mildew (Gibberella zeae), red rust (Puccinia recondita), brown snow blight (Pythium iwayamai), red snow blight (Monographella nivalis), eyelid Disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow blight (Typhula incarnata), snow blight (Myriosclerotinia borealis), blight (Gaeumanomyces graminis graminis) ), Ergot disease (Claviceps purpurea), lumber scab (Tilletia caries), bare black scion (Ustilago nuda), etc. Barley: plague (Pyrenophora graminea), web blight (Pyrenophora teres), cloud disease (Rhynchosporium secalis), Bare scab (Ustilago tritici, U. nuda), etc. Rice: Pyricularia (Pyricularia oryzae), sheath blight (Rhizoctonia solani), fool seedling (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicolum , Blight leaf blight (Xanthomonas oryzae), seedling blight (Burkholderia plantarii), brown leaf blight (Acidovorax avenae), leaf blight (Burkholderia glumae), leaf blight (Cercospora oryzae), rice blight (Ustiliginoidea) virens), brown rice (Alternaria alternata, Curvularia intermedia), belly black rice (Alternaria padwickii), reddish rice (Epicoccam purpurascens), etc. Tobacco: sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), epiphylosis ), Etc. Tulip: Gray mold (Botrytis cinerea), etc. Sunflower: Downy mildew (Plasmopara halstedii), sclerotis disease (Sclerotinia sclerotiorum), etc. Bentograss: snowfever sclerotis (Sclerotinia borealis), large patch (Rhizoctonia solani) , Dollar spot (Sclerotinia homoeocarpa), rice blast (Pyricularia sp.), Red burn (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola) Orchardgrass: powdery mildew (Erysiphe graminis) and other soybeans: purpura (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem blight (Phytophthora sojae), rust (Phakopsora pachyrhizi), sclerotis disease (Sclerotinia sclerotirum) Anthracnose (Colletotrichum truncatum), Botrytis cinerea, etc. Potato: Phytophthora infestans, summer plague (Aleternaria solani), black-spot (Thanatophorus cucumeris), etc. Banana: Panama disease (Fusarium oxysporum), Shigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola) etc. Rape: Sclerotinia sclerotiorum, Rheumatoid disease (Phoma lingam), black spot (Alternaria brassicae) etc. Coffee: rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum, Brown eye disease (Cercospora coffeicola) etc. Sugar cane: Brown rust disease (Puccinia melanocephala etc.) Corn: Hemorrhoids Gloecercospora sorghi), rust (Puccinia sorghi), southern leaf rust (Puccinia polysora), black scab (Ustilago maydis), sesame leaf blight (Cochliobolus heterostrophus), soot disease (Setophaeria turcica) etc. Cotton: Seedling blight Pythium sp), rust (Phakopsora gossypii), mildew (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc.

  The insecticide or acaricide of the present invention is excellent in the control effect of various agricultural pests and pests such as mites which affect the growth of plants. The insecticidal or acaricidal agent of the present invention is effective not only for susceptible strains, but also for pests of strains in which resistance to conventional drugs such as organophosphorus agents and carbamate agents has developed. As representative examples of the pests of the resistant strain, diamondback moth, planthoppers, leafhoppers, aphids and the like can be mentioned.

  The pest control agent of the present invention is effective in controlling pests other than agricultural pests and mites. As pests, for example, ectoparasites, hygiene pests and the like can be mentioned.

The plants to which the agricultural and horticultural fungicides, pest control agents, and insecticidal or acaricidal agents of the present invention can be applied include cereals, vegetables, root vegetables, potatoes, trees, grasses, grasses, etc. Can be mentioned.
The agricultural and horticultural fungicides, pest control agents, and insecticidal or acaricidal agents of the present invention can be obtained by using various parts of plants, such as leaves, stems, handles, flowers, buds, fruits, seeds, sprouts, roots, tubers, It can be applied to tubers, shoots, cuttings and the like. In addition, improved varieties and varieties, cultivars, mutants, hybrids and genetically modified organisms (GMOs) of these plants can also be targeted.

  The fungicide for agricultural and horticultural use of the present invention is used for seed treatment, foliage application, soil application, water surface application, etc. which are carried out to control various diseases occurring in agricultural and horticultural crops including florets, turf and grass. Can.

The agricultural and horticultural fungicides, pest control agents, and insecticidal or acaricidal fungicides for agricultural and horticultural purposes of the present invention are other agricultural and horticultural products having effects such as sterilization, insecticidal and acaricidal agents, nematodes, insecticidal insect pests, etc. Drugs for use; They may be mixed with or used together with plant growth regulators, synergists, fertilizers, soil conditioners, animal feeds and the like.
An example is shown below.
Fungicide:
(1) Nucleic acid biosynthesis inhibitors:
(A) RNA polymerase I inhibitors: Benalaxil, Benalaxyl-M, fralaxyl, metalaxyl, metalaxyl-M; oxadixyl; cloziracone, off-race;
(B) adenosine deaminase inhibitors: bupirimate, dimethymol, ethylimol;
(C) DNA / RNA synthesis inhibitors: hymexazole, octyrilinone;
(D) DNA topoisomerase II inhibitor: oxophosphate;

(2) Mitotic proliferation inhibitors and cytostatics:
(A) β-tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl (thiophanate-methyl); dietophencarb, zoxamide, etaboxam;
(B) cell division inhibitors: penciclone;
(C) Delocalization inhibitors 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; isofetamide; fluopyram; fenfuram, flumeclox; , Flumetopyr, isopyrazam, penflufen, penthiopyrade, sedaxane; boscalid;
(C) complex III ubiquinol oxidase Qo inhibitors: azoxystrobin, spiderxystrobin, quaxitostrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraxtrobin; pyraclostrobin, Crayoxime-methyl, trifloxystrobin; dimoxystrobin, phenaminstrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; phenamidon; pyribencarb
(D) Complex III ubiquinol reductase Qi inhibitors: Cyazofamid; amisulbrom;
(E) Uncoupling agent for oxidative phosphorylation: vinapacryl, meptylizino cup, dino cup; fluazinam; ferimzone;
(F) Oxidative phosphorylation inhibitors (inhibitors of ATP synthetase): phentin acetate, phentin chloride, phentin hydrochloride;
(G) ATP production inhibitor: silthiofam;
(H) Complex III: Qx (unknown) inhibitor of thyrochrome bc1 (ubiquinone reductase): Amethocrazine;

(4) Amino acid and protein synthesis inhibitors (a) Methionine biosynthesis inhibitors: Andprim, cyprodinil, mepanipyrim, pyrimethanyl;
(B) Protein synthesis inhibitors: Blasticidin-S; Kasugamycin, Kasugamycin hydrochloride; Streptomycin; Oxytetracycline;

(5) Signal transduction inhibitors:
(A) Signal transduction inhibitors: quinoxyfene, proquinazide;
(B) MAP and histidine kinase inhibitors in osmotic signal transduction: fen picronil, fludioxonil; crozolimate, iprodione, procymidone, vinclozolin;

(6) Lipid and cell membrane synthesis inhibitors:
(A) Phospholipid biosynthesis, methyl trans-ferase inhibitor: edifenphos, iprovenphos, pyrazophos; isoprothiolane;
(B) lipid peroxides: biphenyl, chloroneb, dichlorane, quindozen, technazen, tolclophos methyl; etordiazole;
(C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb bosecetate, prothiocarb;
(D) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(E) Agents that disrupt cell membranes: extracts of Goseika Jupte (tea tree);

(7) Sterol biosynthesis inhibitor of cell membrane:
(A) Demethylation inhibitors at position C14 in sterol biosynthesis: Trifolin; pyriphenox, pyriisoxazole; phenarimol, flurprimidol, nualimol; imazaryl, imazalil sulfate, oxosconazole, pefrazoate, prochloraz, Triflumizole, biniconazole;
Azaconazole, vitertanol, bromuconazole, cyproconazole, diclobutrazol, difenoconazole, diniconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinonazole, flusilazole, flutriaazole), fluconazole, fluconazole- Cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, quinconazole, cimeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole;
(B) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperaline; spiroxamine;
(C) 3-keto reductase inhibitors at C4 demethylation of sterol biosynthesis system: fenhexamid; fenpyrazamine;
(D) squalene epoxidase inhibitors of sterol biosynthesis system: pyributycarb; naftifene, terbinafine;

(8) Cell wall synthesis inhibition (a) Trehalase inhibitor: Validamycin;
(B) Chitin synthetase inhibitors: polyoxins, polyoxolims;
(C) Cellulose synthetase inhibitors: Dimethomorph, flumorph, pirimorph; bench abariculum, iprobicarb, tolprocarb, varifenalate; mandipropamide;

(9) Melanin Biosynthesis Inhibitor (a) Reductase Inhibitor of Melanin Biosynthesis: Phthalide; Pyroquirone; Tricyclazole;
(B) Dehydratase inhibitors of melanin biosynthesis: Carpropamide; diclocimet; phenoxanyl;

(10) Host plant resistance inducer:
(A) Agents that act on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(B) Others: Probenazole; Thiazinyl; Isotianil; Laminarin;

(11) Agents with unknown activity: Shimoxanyl, fosetylaluminum, phosphoric acid (phosphate), teclophthalam, triazoloxide, flusulfamide, diclomedin, metasulfocarb, cyfluphenamide, metrafenone, pyrofenone, dodine, dodine free base, flutianil;

(12) Agents having multiple action points: copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur product, calcium polysulfide; faram, mancozeb, maneb) , Mankapper, methylam, polycarbamate, propineb, tilam, zineb, ziram; captan, captaphor, phorpet; chlorothalonil; diclofluanid, tolylfluanid; gazatine, iminectazine acetate, iminoctazine albesylate albesylate; anilazine; dithianone Quinomethionate; fluorimide;

(13) Other agents: DBEDC, fluorophorpet, gazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofram, agrobacteria, betoxazine, diphenylamine, methylisothianate (MITC ), Mildeomycin, Capsaicin, Kuflaneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophen, Diphenzoquat, Diphenzoquat Methylsulfonate, Flumethobel, Fosetyl Calcium, Fosetyl Sodium, Irumamycin, Natamycin, Nitrotal Isopropyl , Oxamocarb, propamocin sodium, pyrrolnitrine, tebufloquine, tornifanide, zalliramide, algophase, amicarthiazole (Amicarthiazol), oxathiathia Piproline (Oxathiapiprolin), methylam zinc, benchazole, trichloramide, uniconazole, mildeomycin, Oxyfenthiin, picarbutrazox (picarbutrazox);

Insecticides, acaricides, nematocides, soil pesticides:
(1) Acetylcholinesterase inhibitors:
(A) Carbamate system: Alanicarb, aldiocarb, benzocarb, benfracarb, butocarboxim, butoxy carboxim, carbaryl, carbofuran, carbosulfan, carbohephan, ethiophene carb, fenobucarb, formetanate, furaiocarb, isocarb, methiocarb, methoyl, oxamyl, piromicarb, propoxal, Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb; phenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixicarb, aminocarb, bufencarb, cloetocarb, metame sodium, promecarb;

(B) Organophosphorus: Acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, kazzaphos, chlorethoxyphos, chlorphenphos, chlormephos, chlorpyrifos, chlorpyriphos-methyl, coumaphos, cyanophos, dimetone-S-methyl, diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylphosphine, Disulfoton, EPN, Ethion, Ethoprophos, Pham Fool, Fenamiphos, Fenitrothion, Fenthione, Fosciate, Heptenophos, Imicifoss, Isophenphos, Isocarbophos, Isoxathion, Malathion, Mecarbammethizophos Methiomethone, Monocrotophos, Naredo, Omethoate, Oxydimethone-Methyl, Parathion, Parathion-Methyl, Fent Tol, Foleto, Phosalone, Phosmet, Phosphamidon, Hoximme, Pirimiphos-Methyl, Profenophos, Propetamphos, Prothiophos, Pyracophos, Pyridafenthion, Quinalphos, Sulfotep, Tebupillinphos, Temephos, Terbuphos, Tetrachlorvinphos, Thiometone, Trichophos, Trichlorophos, Vamidothion; Bromophos Ethyl, BRP, Carbophenothione, Cyanophenphos, CYAP, Dimetone-S-Methylsulfone, Diariphos, Diclofenthion, Dioxabenzophos, Etriphos, Phensulfothion, Flupirazophos, Honophos, Formothion, Phosmethyrane, Isazophos, Iodophenphos, Methacrylos, pyrimiphos-ethyl, phosphocarb, propaphos, protoate, sulprofos;

(2) GABA-agonizing chloride channel antagonist: chlordene, endosulfan, ethiprole, fipronil, pyrafluprol, pyriprol; campechlor, heptachlor;
(3) Sodium channel modulators: acrolinathrin, d-cis-trans arethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cypophothrin [(1R) -trans isomer], deltamethrin, enpentrin [(EZ)-( 1R)-isomer], esfenvalerate, etofenprox, fenpropatrin, fenvalerate, flucithinate, flumethrin, tau-fluvalinate, halfenprox, imipuri Phosphorus, cadestrin, permethrin, phenothrin [(1R) -trans isomer], prarethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin; allethrin, pyrethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, phenpyritrin, flubrositrinate, flufenprox, metfluthrin, protrifenbuto, pyrethmethrin, terraretrin;

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine; flupyradifurone;
(5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad;
(6) Chloride channel activators: Abamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime;
(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diofenolan, epofenonan, triprene;
(8) Other nonspecific inhibitors: methyl bromide, chlorpicrin, sulfuryl fluoride, borax, tartaric acid;
(9) Homoptera order selective antifeedants: flonicamide, pimetrodine, pyrifluquinazone;

(10) Acaricide growth inhibitors: clofenthezin, difrobidazine, hexythiazox, etoxazole;
(11) Microorganisms derived from insect midgut inner membrane disrupter: Bacillus thuringiensis subsp. Islaerensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Eiwai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Teneburionis, Bt Crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1;
(12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradiphone;
(13) Oxidative phosphorylation uncoupling agent: chlorfenapyr, sulframide, DNOC; binapacryl, dinobuton, dinocup;
(14) Nicotinic acetylcholine receptor channel blocker: bensultap, cartap hydrochloride; nereistoxin; thiosultap monosodium salt, thiocyclam;
(15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxulon, flufenoxuron, hexaflumuron, lufenuron, novallone, noviflumuron, teflubenzurone, triflumuron, buprofezin, fluazulon;
(16) Dipteran molt-disrupting agents: cyromazine;
(17) molting hormone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide;
(18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform;
(19) Mitochondrial electron transport complex III inhibitor: acequinosyl, fluacripyrim, hydramethylnon;
(20) Mitochondrial electron transport complex I inhibitor: phenazaquin, fenproximate, pyrimidifen, pyridaben, tebufenpyrade, tolfenpyrade, rotenone;

(21) Voltage-gated sodium channel blockers: indoxacarb, metaflumizone;
(22) Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirtetramat;
(23) Mitochondrial electron transport complex IV inhibitor: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
(24) Mitochondrial electron transport complex II inhibitor: sienopyrafen, ciflumethofen, piflubumid;
(25) Ryanodine receptor modulators: chloranthraniliprole, cyantraniprole, flubendiamide, cyclaniliprole, tetraniliprole;
(26) Mixed function oxidase inhibitor compound: piperonyl butoxide;
(27) Latrophin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
(28) Other agents (the mechanism of action is unknown): azadirachtin, benzoxmate, biphenazate, bromopropilate, quinomethionate, cryolite, dichophor, pyridalyl; benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP , Phenisobromolate, benzomate, methaldehyde, chlorobenzylate, crothiazoben, dicyclanyl, phenoxacrim, phentrifanyl, flubenzamine, fluphenadine, gossypua, japonirua, methoxadiazon, petroleum, potassium oleate, tetrasul, triaracene; afidopyropen), flomethoquin, flufiprole, fluensulphone, meperfursulin, tetramethylfursulin, tralopyril, dimeflusulin, meme Fluneolane, afoxolane, fluxamethamide, 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, and other metadiamides;

[Formulation prescription]
The agricultural and horticultural fungicides, pest control agents, and insecticidal or acaricidal agents of the present invention are not particularly limited by the dosage form. For example, dosage forms such as wettable powders, emulsions, aqueous solvents, water dispersible granules, powders, tablets and the like can be mentioned. The preparation method for the preparation is not particularly limited, and known preparation methods can be adopted depending on the dosage form.
Although some formulations are shown below, the additives and the addition ratio should not be limited to these examples, but can be widely varied. Parts in the formulation indicate parts by weight.

  Some formulation examples are shown. In addition, the pharmaceutical formulation shown below is a mere illustration, and can be corrected in the range which does not violate the main point of this invention.

(Formulation 1: wettable powder)
The compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfuric acid ester 4 parts Alkyl naphthalene sulfonate 3 parts The above components are uniformly mixed and finely ground to obtain a wettable powder with an active ingredient of 40%.

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

(Formulation 3: granules)
The compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts The above are uniformly mixed and finely ground, and then granulated into particles of 0.5 to 1.0 mm in diameter to obtain 5% active ingredient Obtain granules of

(Formulation 4: granules)
The compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part The above is well ground and mixed well, water is added and thoroughly mixed, then it is granulated and dried to have 5% active ingredient Obtain granules of

(Formulation 5: suspension agent)
The 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 are mixed and wet-pulverized until the particle size becomes 3 microns or less A 10% suspension of the active ingredient is obtained.

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

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

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

Mix 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, and mix 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 desired compound. The yield was 38%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.99 (3H, s), 2.29 (3H, s), 2.34 (3H, s), 2.58 (3H, s), 10.42 (1H, br.s)

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

1.5 g of 4-trifluoromethylbenzyl bromide were dissolved in 20 ml of acetonitrile. To this solution was added 1.2 g of tert-butyl N-hydroxycarbamate and 1.7 g of 1,8-diazabicyclo [5.4.0] -undec-7-ene, and the mixture was stirred at room temperature for 1 hour. After that, the reaction solution was poured into 1 N 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%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.48 (9 H, s), 4.91 (2 H, s), 7. 15 (1 H, br. S), 7.51 (2 H, d), 7.63 (2 H, d)

(Step 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 was 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 bicarbonate and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was washed with ethyl acetate to obtain 0.20 g of the objective compound. The yield was 34%.
Physical properties of the objective compound were as follows.
¹ H-NMR (DMSO-d ₆ , δ ppm) 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)

(Step 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 were added 45 mg of pyridine and 43 mg of acetyl chloride, and the mixture was stirred overnight at room temperature. Thereafter, the reaction solution was diluted with chloroform, washed with 1 N hydrochloric acid, then washed with saturated aqueous sodium bicarbonate solution, 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%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 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)
Preparation of 1- (4-Acetoxy-2,5,6-trimethylpyridin-3-yl) ethanone O- {2- (4-trifluoromethylphenyl) ethyl} oxime

(Step 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 was added 2.07 g of triphenylphosphine. To this solution was dropped 3.43 g of a 40% toluene solution of diethyl azodicarboxylate under ice-cooling. The reaction was warmed to room temperature and stirred overnight. Thereafter, the solvent was distilled off under reduced pressure. The resulting 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%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 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)

(Step 2)
Synthesis of O- {2- (4-Trifluoromethylphenyl) ethyl} hydroxylamine

1.44 g of N- {2- (4-trifluoromethylphenyl) ethoxy} phthalimide were dissolved in 20 ml of dichloromethane. The solution was cooled to 0 ° C. and 0.22 g of methylhydrazine was added dropwise. The reaction was stirred at 0 ° C. for 1.5 hours. Thereafter, diethyl ether was added and the insoluble matter was separated by filtration. The solvent was distilled off under reduced pressure to obtain 0.83 g of the objective compound. The yield was 94%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 2.96 (2 H, t), _3. 90 (2 H, t), 5.43 (2 H, br. S), 7.33 (2 H, d), 7.55 (2 H, d)

(Step 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 was added 0.50 g of 1- (4-hydroxy-2,5,6-trimethylpyridin-3-yl) ethanone and 1 ml of trifluoroacetic acid, and the mixture was stirred overnight at room temperature. Thereafter, the reaction solution was poured into saturated aqueous sodium bicarbonate and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was washed with diethyl ether to obtain 0.68 g of the objective compound. The yield was 67%.
Physical properties of the objective compound were as follows.
¹ H-NMR (DMSO-d ₆ , δ ppm) 1.79 (3 H, s), 1. 88 (3 H, s), 2. 11 (3 H, s), 2. 19 (3 H, s), 3.00 (2 H, t), 4.23 (2 H) , t), 7.49 (2H, d), 7.64 (2H, d), 10.96 (1H, br.s)

(Step 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. 0.19 g of triethylamine and 0.13 g of acetyl chloride were added to this solution and stirred overnight at room temperature. After that, the reaction solution was concentrated under reduced pressure, and the obtained 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%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 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)
Preparation of 1- (4-Acetoxy-2,5,6-trimethylpyridin-3-yl) ethanone O- (4-trifluoromethylphenyl) oxime

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

2.0 g of 4-fluorobenzotrifluoride were 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. Then, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and finally dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 4/1 (volume ratio)) to obtain 1.5 g of the objective compound. The yield was 44%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.50 (9 H, s), 7. 19 (2 H, d), 7. 50 (1 H, s), 7.56 (2 H, d)

(Step 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 bicarbonate and extracted with chloroform. The organic layer was washed with brine and finally dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was washed with diethyl ether to obtain 0.39 g of the objective compound. The yield was 41%.
Physical properties of the objective compound were as follows.
¹ H-NMR (DMSO-d ₆ , δ ppm) 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)

(Step 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. Triethylamine 0.10g and 70 mg of acetyl chlorides were added to this solution, and it stirred at room temperature overnight. Then, the reaction liquid was concentrated under reduced pressure, and the obtained 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%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 2.10 (3 H, s), 2.23 (3 H, s), 2. 32 (3 H, s), 2.50 (3 H, s), 2.55 (3 H, s), 7. 27 (2 H, 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

(Step 1)
Synthesis of ethyl 4-hydroxy-2,5,6-trimethylnicotinate

45 g of ethyl 3-aminocrotonate and 50 g of ethyl 2-methylacetoacetate were dissolved in 100 ml of xylene. 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 objective compound. The yield was 33%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.21 (3H, t), 2.14 (3H, s), 2.46 (3H, s), 2.71 (3H, s), 4.45 (2H, q), 12.14 (3H, s) )

(Step 2)
Synthesis of ethyl 4-methoxy-2,5,6-trimethylnicotinate

12.2 g of ethyl 4-hydroxy-2,5,6-trimethylnicotinate were dissolved in 120 ml of acetone. 21.0 g of cesium carbonate and then 10.0 g of methyl iodide were added to this solution, and the mixture was heated to reflux for 8 hours. After that, the reaction solution was cooled to room temperature, poured into water and extracted with ethyl acetate. The organic layer was washed with brine and finally dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 10.0 g of the objective compound. The yield was 77%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.40 (3H, t), 2.17 (3H, s), 2.48 (6H, s), 3.86 (3H, s) 4.41 (2H, q)

(Step 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. Under ice cooling, 10.0 g of ethyl 4-methoxy-2,5,6-trimethylnicotinate was added dropwise to this solution. After the addition was completed, 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 objective compound. The yield was 97%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 2.18 (3H, s), 2.48 (3H, s), 2.56 (3H, s), 3.81 (3H, s), 4.72 (2H, s)

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

7.9 g of (4-methoxy-2,5,6-trimethylpyridin-3-yl) -methanol were dissolved in 90 ml of benzene. To this solution was added 15.2 g of manganese dioxide, and the mixture was 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 objective compound. The yield was 77%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 2.22 (3 H, s), 2.53 (3 H, s), 2. 73 (3 H, s), 3. 87 (3 H, s), 10. 50 (1 H, s)

(Step 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 was added dropwise 33 ml of 1N boron tribromide-dichloromethane solution under ice-cooling. After the addition was completed, 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 objective compound. The yield was 33%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 2.18 (3 H, s), 2.43 (3 H, s), 2.53 (3 H, s), 10. 46 (1 H, 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 was added 0.26 g of 4-hydroxy-2,5,6-trimethylpyridine-3-carbaldehyde and a few drops of trifluoroacetic acid, and the mixture was stirred overnight at room temperature. Thereafter, the reaction solution was poured into saturated aqueous sodium bicarbonate and extracted with chloroform. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was washed with diethyl ether to obtain 0.42 g of the objective compound. The yield was 76%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 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 (1 H, 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. 0.22 g of triethylamine was added to this solution. Then, under ice cooling, 0.14 g of acetyl chloride was added, and the mixture was stirred overnight at room temperature. Thereafter, the reaction solution was poured into saturated aqueous sodium bicarbonate and extracted with chloroform. The organic layer was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.37 g of the objective compound. The yield was 79%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 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 (1 H, s)

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

(Step 1)
Synthesis of methyl 4-hydroxy-2-ethyl-5,6-dimethyl nicotinate

Mix 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 and stir at 150 ° C. for 5 hours did. After cooling to room temperature, the precipitated crystals were filtered, washed with diethyl ether and dried to obtain 13.7 g of the objective compound. 31% yield
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.21 (3H, t), 2.14 (3H, s), 2.46 (3H, s), 2.71 (2H, q), 3.89 (3H, s)

(Step 2)
Synthesis of methyl 4-allyloxy-2-ethyl-5,6-dimethyl nicotinate

13.7 g of methyl 4-hydroxy-2-ethyl-5,6-dimethyl nicotinate were 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 objective compound. 100% yield.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 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 (1 H, m)

(Step 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 was added dropwise 16.6 g of methyl 4-allyloxy-2-ethyl-5,6-dimethyl nicotinate under ice cooling, and after completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours. Thereafter, the reaction solution was ice-cooled, water was added until unreacted lithium sodium hydride was decomposed, and the solution was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 11.3 g of the objective compound. 77% yield.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.26 (3 H, t), 2.16 (3 H, s), 2. 46 (3 H, s), 2. 84 (2 H, q), 4. 39 (2 H, d), 4. 70 (2 H, d) ), 5.29-5.45 (2H, m), 6.03-6. 14 (1 H, m)

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

Dissolve 11.3 g of (4-allyloxy-2-ethyl-5,6-dimethylpyridin-3-yl) -methanol in 120 ml of dichloromethane, and under ice-cooling 120 ml of saturated aqueous sodium bicarbonate solution, 0.6 g of potassium bromide, 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 the dropwise addition, 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 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 obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 11.1 g of the objective compound. 99% yield.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.25 (3 H, t), 2.21 (3 H, s), 2.52 (3 H, s), 3.06 (2 H, q), 4.42 (2 H, d), 5.32-5. 43 (2 H) , m), 6.01-6.11 (1 H, m), 10. 47 (1 H, s)

(Step 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. Into this reaction solution, under ice-cooling, O- [2-[[3-chloro-5- (trifluoromethyl) -2-pyridyl] oxy] -1-methyl-propyl] hydroxylamine 0.8 g, trifluoroacetic acid Add a few drops and stir overnight at room temperature. The reaction solution was poured into saturated aqueous sodium bicarbonate solution and extracted with chloroform, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.75 g of the target compound. Yield 68%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.19-1.43 (9 H, m), 2.21 (3 H, s), 2.52 (3 H, s), 3.06 (2 H, q), 4.33-4. 42 (3 H, m), 5.32 -5.43 (2H, m), 5.57-5.61 (1 H, m), 6.01-6.11 (1 H, m), 7.79-8.25 (3 H, m)

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

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. 0.012 g of tetrakistriphenylphosphine palladium and 0.28 g of potassium carbonate were added to this solution, 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 obtained residue was washed with diethyl ether to obtain 0.4 g of the objective compound. Yield 87%.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.17-1.41 (9 H, m), 1.99 (3 H, s), 2.22 (3 H, s), 2. 85 (2 H, q), 4.33-4. 42 (1 H, m), 5.57 -5.61 (1 H, m), 7.78-8.22 (3 H, 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 .4 g was dissolved in 10 ml chloroform. After 0.2 g of triethylamine was added 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 solution and extracted with chloroform, and then the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.37 g of the objective compound. 84% yield.
Physical properties of the objective compound were as follows.
¹ H-NMR (CDCl ₃ , δ ppm) 1.19-1.43 (9 H, m), 2.06 (3 H, s), 2.30 (3 H, s), 2.51 (3 H, s), 2.86 (2 H, q), 4.43-4. 45 (1 H, m), 5.59-5. 62 (1 H, m), 7.82-8. 26 (3 H, m)

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

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

Tables 2 to 6 show, among the compounds represented by the formula (I), compounds represented by the formula (I-2 shown below) in which Q is an organic group represented by the formula (II) Compounds) are disclosed. 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 to which * is attached in the structural formula of “B ^a ” indicates a carbon atom to be bonded to the oxygen of oxime (the same meaning is indicated in the following tables). Furthermore, the carbon atom or nitrogen atom with ** in the structural formula of “B ^a ” indicates a carbon atom or nitrogen atom to be bonded to “Ar ² ” (the same meaning is shown in the following tables).
Compound c-187 in Table 3 is an N-oxide.

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

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

¹ H-NMR data are given in Table 11 for some of the compounds listed in Tables 1 to 10 above.

[Biological test]
The following test examples show that the compound of the present invention is useful as an active ingredient of agricultural and horticultural fungicides.

Test Example 1 Wheat powdery mildew control test 1
5 parts by mass of the compound of the present invention was dissolved in 95 parts by mass of a dimethylformamide solution containing 1.5% of polyoxyethylene sorbitan monolaurate to prepare an emulsion of 5% of the active ingredient.
The above 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. Then, the said chemical | medical solution was sprayed to the wheat seedling (cultivar "Chihoku", 1.0-1.2 leaf stage) grown by the unglazed pot. The leaves were allowed to air dry. Thereafter, conidia of wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) were shaken off and inoculated, and kept in a greenhouse at 22-25 ° C. for 7 days (treatment). On the other hand, wheat seedling was shaken off and inoculated with conidia of wheat powdery mildew without spraying with a chemical solution, and was maintained in a greenhouse at 22-25 ° C. for 7 days (untreated). The appearance of lesions on the leaves was compared with the untreated area. The control value was calculated.
Control value (%) = 100− {area on which a lesion appeared (treatment) / area on which a lesion appeared (no treatment)} × 100

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

Test Example 2 Wheat leaf rust control 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 said chemical | medical solution was sprayed on the wheat seedling (variety "Agriculture No. 61", 1.0-1.2 leaf stage) grown by the unglazed pot. The leaves were allowed to air dry. Thereafter, N. spores of wheat rust fungus (Puccinia recondita) were shaken off and inoculated, and kept in a greenhouse at 22 to 25 ° C. for 10 days. In the same manner as in Test Example 1, the appearance of lesions on the leaves was compared with that in the non-treated case, and the control value was calculated.

  A wheat leaf rust control test was conducted on the compounds shown in Table 13. All compounds had a control value of 75% or more.

Test Example 3 Wheat powdery mildew control test 2
5.62 parts by mass of the compound of the present invention, 4.49 parts by mass of a surfactant and 89.89 parts by mass of dimethylformamide were mixed and dissolved to obtain an emulsion having an active ingredient of 5.62%.
The above emulsion was diluted with water to an active ingredient of 125 ppm to obtain a drug solution. The said chemical | medical solution was sprayed to the wheat seedling (variety "chihoku", 1.0-1.2 leaf stage) grown by the unglazed pot. After leaves were air-dried, conidia of wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) were shaken off and inoculated, and kept in a greenhouse at 20 to 25 ° C for 7 days. In the same manner as in Test Example 1, the appearance of lesions on the leaves was compared with that in the non-treated case, and the control value was calculated.

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

(Test Example 4) Wheat leaf 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 to the wheat seedling (variety "Agriculture No. 61", 1.0-1.2 leaf stage) grown by the unglazed pot. After air-drying the leaves, N. spores of wheat rust fungus (Puccinia recondita) were shaken off and inoculated, and kept in a greenhouse at 20-25 ° C for 10 days. In the same manner as in Test Example 1, the appearance of lesions on the leaves was compared with that in the non-treated case, and the control value was calculated.

The wheat leaf rust control test shown in Table 15 was conducted. All compounds showed a control value of 75% or more.

  The following test examples show that the compounds of the present invention are useful as an active ingredient of insecticides or acaricides.

Test Example 5 Test for Confirming Efficacy against Hastomone spp. 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 alkyl aryl ether are mixed and dissolved to obtain an emulsion of active ingredient 5% Prepared.
The emulsion was diluted with water to obtain a drug having a compound concentration of 125 ppm. The cabbage leaves were dipped in the solution for 30 seconds and then air-dried. Thereafter, cabbage leaves were placed in a petri dish covered with filter paper, and five second-instar larvae of the lotus root were inoculated. The glass lid was placed and placed in a constant temperature and humidity chamber with a temperature of 25 ° C. and a humidity of 65%, and after 5 days, the life and death of the cassava was examined to calculate the insecticidal rate. The test was performed in duplicate.

  The compounds shown in Table 16 were subjected to the efficacy confirmation test against the Japanese mustard spider. 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 that of Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm.
Adult cotton aphids were inoculated on the first true leaves of 10-day-old sprouted cucumber which were sown in a 3-inch bowl. One day later, the adults were removed, and the solution was sprayed onto cucumbers which are parasitic to the born juveniles. It was placed in a constant temperature and humidity chamber with a temperature of 25 ° C. and a humidity of 65%, and after 5 days, life and death of cotton aphids were examined to calculate the insecticidal rate. The test was performed in duplicate.

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

Test Example 7 Test for Confirming Efficacy against Nami spider mite The emulsion prepared by the same method as in Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. Ten adult female spider spider mites were inoculated on the first true leaves of green beans which had been germinated 10 days after sowing in three-inch pots. One day later, the drug solution was sprayed. It was placed in a constant temperature and humidity chamber with a temperature of 25 ° C. and a humidity of 65%, and after 3 days, the mortality of the spider spider mite was examined to calculate the insecticidal rate. The test was performed in duplicate.

  The compounds shown in Table 18 were subjected to efficacy confirmation tests against two-spotted spider mite. All compounds had an insecticidal rate of 100%.

Test Example 8 Test for Confirming Efficacy against Bean Aphid The emulsion prepared by the same method as in Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. The cowpea was raised in a 3-inch bowl and inoculated with bean aphid nymphs on primary leaves. The above drug solution was sprayed on cowpea which is infested with the black-and-white bream beetle nymphs. The cowpea was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%, and after 4 days, the aphids were checked for life and death. The test was performed in duplicate.

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

Test Example 9 Efficacy Confirmation Test for Kanzawa spider mite The emulsion prepared by the same method as that of Test Example 5 was diluted with water to obtain a chemical solution having a compound concentration of 125 ppm. The green beans were raised in a 3-inch bowl, and 10 adult females of the red spider mite Kanzawa spider mite were inoculated on the primary leaves. The medicinal solution was sprayed on green bean seedlings. The green beans were placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 65%, and 10 days after spraying, adults were examined for life and death.

  The compounds shown in Table 20 were subjected to efficacy confirmation tests against Kanzawa spider mite. Each compound had an insecticidal rate of 90% or more.

The pyridine compound according to the present invention is a novel compound having the effects of pest control, sterilization, acaricide, insecticidal and the like, causing no adverse effects on plants, and having little toxicity to human and fish and environmental impact. . In particular, it exhibits excellent control effects 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 insecticidal or acaricidal agents. Therefore, the pyridine compound of the present invention is industrially useful.

Claims (4)

The compound or its salt represented by a formula (I).

[In the 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 And an aryl group of 10 to 10, a 3 to 6 membered heterocyclyl group which is unsubstituted or 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 a G ¹ substituted C1-6 alkoxy group, a formyl group, a formyloxy group, an unsubstituted or G ¹ substituted C1-6 alkylcarbonyl group, an unsubstituted or G ¹ substituted C1-6 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 each of R ¹ and R ² is 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ア ル キ ニ 6 alkynyl group, unsubstituted or G ¹ substituted C 3-8 cycloalkyl group, unsubstituted or G ² substituted C ⁶ to 10 aryl C ¹ 6 alkyl group, unsubstituted or substituted G ² 3 to 6 membered heterocyclyl group, unsubstituted or G ² substituted 3 to 6 membered heterocyclyl group C1-6 alkyl group, formyl group, unsubstituted or G ¹ substituted C1-6 alkyl carbonyl group , 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 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, ^The 3- to 6-membered heterocyclyl group substituted by ² is shown.
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 ( It represents a divalent group represented by a thio) group or -O-C (= O) -N ( ^Gb )-.
* Indicates the bonding position of the group represented by formula (IV).
Q represents any one of the organic groups represented by Formula (II) or Formula (III).

[In the formula (II) and the 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 an unsubstituted or G ² substituted C ⁶ to 10 aryl group, an unsubstituted or G ² substituted C ⁶ to 10 aryloxy group, an unsubstituted or G ² substituted C ⁶ to 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 a C ² to C 6 alkylene group which is unsubstituted or substituted by G ⁴ , a C 2 to C 6 alkenylene group which is unsubstituted or substituted by G ⁴ , C ² to C 6 alkynylene which is unsubstituted or substituted by 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 3 to 6 membered heterocyclylene group which is unsubstituted or substituted by G ⁴ .
In addition, ^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.
* Represents the bonding position of the organic group represented by Formula (II) or Formula (III). ]
G ¹ represents a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkoxy group, a C1-6 alkoxycarbonyl group, a formyloxy group, a C1-6 alkylcarbonyloxy group, a C1-6 alkoxycarbonyloxy group, a cyano Group or a halogeno group is shown. 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, Cl to 6 alkyl group, hydroxyalkyl Cl to 6 alkyl groups, C2-6 alkenyl groups, C2-6 alkynyl groups, C3-8 cycloalkyl groups, Cl to 6 haloalkyl, Cl to 6 alkoxy Cl to 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 alkylcarbonyl Oxy group, C1-6 alkoxy carbonyloxy group, C1-6 alkoxy carbonyl 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 To 10 aryloxy group, an unsubstituted or G ²¹ -substituted 3- to 6-membered heterocyclyl group, an unsubstituted or G ²¹ -substituted 3- to 6-membered heterocyclyloxy group, a C 1-6 alkylthio group, C 1 to 6 Alkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, pentafluorosulfanyl group, unsubstituted or C6-10 substituted with G ²¹ Arylthio group, unsubstituted or G ²¹ substituted C 6-10 arylsulfinyl group, 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 It may be the same or different.
G ²¹ represents a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 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 3 to 6 membered heterocyclyl group, cyano group, halogeno group, C1-6 alkylene group, C1-6 alkylenedioxy group, oxo group, C3-8 cycloalkyl C1-6 alkyl group, unsubstituted or 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. ]   An agricultural and horticultural fungicide containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.   A pest control agent containing, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.   An insecticide or acaricide comprising at least one member selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.