TW201605800A - Pyridine compound and use thereof - Google Patents

Abstract

The present invention provides a compound represented by formula (I) (in the formula, R1, R2, R3 and R4 each represent a hydrogen atom, a C1-6 alkyl group or the like, R1 and R2 may bond to form a 5- to 6-membered ring together with the carbon atoms bonded with R1 and R2, Q represents an organic group represented by formula (II) or the like (in formula (II), Ar1 represents a C6-10 aryl group or the like, R<SP>a</SP> represents a hydrogen atom, a C1-6 alkyl group or the like, * represents the bonding position of the organic group represented by formula (II))) or salt thereof, and also provides a fungicide for agricultural and horticultural use, a harmful organism control agent, and an insecticide or acaricide including at least one selected from the group consisting of the compound represented by formula (I) and salt thereof as an active ingredient.

Description

Pyridine compound and its use

The present invention relates to a pyridine compound, and an agricultural and horticultural fungicide, a pest control agent, and an insecticidal or acaricidal agent.

When cultivating agricultural and horticultural crops, there are many control agents for crop diseases, but it is difficult to call them a sufficiently satisfactory anti-drug for the following reasons: their control effect is insufficient; or due to the presence of drugs The pathogenic bacteria of tolerance are limited in their use; they may cause phytotoxicity or pollution to plants; or they may have toxicity to human and animal fish or have a greater impact on the environment. Therefore, it is strongly desired to have a drug that is less safe to use.

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

[Patent Document 1] WO 2003/103667A

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

In order to solve the above problems, research has been conducted, and as a result, the present invention including the following aspects has been completed.

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

[In the formula (I), R ¹ represents a hydrogen atom, unsubstituted or ^{substituted. 1} G of C1 ~ 6 alkyl, unsubstituted or ^{substituted. 1} G of C1 ~ 6 alkoxy, unsubstituted or G ² substituted C6~10 aryl, unsubstituted or G ² substituted 3-6 membered heterocyclic group, cyano group or halogen group.

R ² and R ³ each independently represent a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 3 -8 cycloalkyl group, unsubstituted or via G ¹ the substituted C1 ~ 6 alkoxy, methyl acyl, carboxylic acyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl carbonyl, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl carbonyloxy a C6-10 aryl group which is unsubstituted or substituted by G ² , (unsubstituted or substituted by a G ¹ C1-6 alkoxyimino group)-C1~6 alkyl group, a cyano group, or a halogen group .

Here, R ¹ and R ² may together form a 5- to 6-membered ring together with the carbon atoms to which each of R ¹ and R ² are bonded.

R ⁴ represents a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 2 -6 alkenyl group, an unsubstituted or G ¹ -substituted C 2 -6 alkynyl group. , unsubstituted or substituted by G ¹ C 3-8 cycloalkyl, unsubstituted or G ² substituted C 6-10 aryl C 1-6 alkyl, unsubstituted or substituted by G ² 3-6 members heterocyclyl, unsubstituted or substituted with G ² of the 3 to 6-membered heterocyclic group a C1 to 6 alkyl, methyl acyl, unsubstituted or substituted with G ¹ of a C1 to 6 alkyl carbonyl, unsubstituted or G ¹ via the C3 ~ 8 cycloalkyl substituted alkylcarbonyl, unsubstituted or substituted with G ¹ group of C1 ~ 6 alkenyl carbonyl group, unsubstituted or substituted with G ² of the C6 ~ 10 aryl-carbonyl group, an unsubstituted or G ¹ -substituted alkoxycarbonyl group substituted by G ¹ , unsubstituted or substituted C 2 6 alkenyloxycarbonyl group by G ¹ , unsubstituted or substituted C ¹ 6 alkylsulfonyl group by G ¹ , unsubstituted or ^one of C1 ~ 6 alkyl substituted aminocarbonyl through G, unsubstituted or substituted with ¹ G of (C1 ~ 6 alkylthio) carbonyl, unsubstituted or substituted with ¹ G of C1 ~ 6 alkyl group (thiocarbonyl) or a group represented by the formula (IV).

In the formula (IV), G ^a each independently represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ - 6 alkyl group, an unsubstituted or G ¹ -substituted C 2 - 6 alkenyl group, unsubstituted or via G ¹ substituents of C2 ~ 6 alkynyl, unsubstituted or substituted with G ¹ of C3 ~ 8 cycloalkyl, or unsubstituted or substituted G ² of the C6 ~ 10 aryl group.

In the formula (IV), G ^b represents a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 2 -6 alkenyl group, unsubstituted or substituted by G ¹ the C2 ~ 6 alkynyl, unsubstituted or substituted with G ¹ of C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ² of the C6 ~ 10 aryl group, or an unsubstituted or substituted by G ² of 3 ~ 6-membered heterocyclic group.

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 group (thio group), a (thio)carbonyloxy group, an oxy group. a divalent group represented by a carbonyl group (thio group) or -OC(=O)-N(G ^b )-.

* indicates the bonding position of the base represented by the formula (IV).

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

[In the formulae (II) and (III), Ar ¹ represents an unsubstituted or G ² -substituted C 6 -10 aryl group, or a 3 - 10 membered heterocyclic group which is unsubstituted or substituted with G ² .

Ar ² represents an unsubstituted or G ² -substituted C 6 -10 aryl group, an unsubstituted or G ² -substituted C 6 -10 aryloxy group, an unsubstituted or G ² -substituted C 6 -10 arylthio group, Unsubstituted or G ² substituted C6-10 sulfinyl, unsubstituted or G ² substituted C6-10 sulfonyl, unsubstituted or substituted by G ² 3~10 members Heterocyclic group, unsubstituted or G ² substituted 3-10 membered heterocyclic oxy group, unsubstituted or G ² substituted 3-10 membered heterocyclic thio or ferrocene group.

R ^a represents a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 3 -8 cycloalkyl group, an amine group, a C 1-6 alkylcarbonylamino group, or C6~10 aryl group which is unsubstituted or substituted by G ² .

B ^a represents an unsubstituted or G ⁴ -substituted C 1 -C 6 alkylene group, an unsubstituted or G ⁴ -substituted C 2 -C 6 alkenylene group, unsubstituted or via G ⁴ Substituted C2~C6 alkynylene group, unsubstituted or G ⁴ substituted C1~C6 alkoxy C1~6 alkyl, unsubstituted or substituted by G ⁴ C3~C6 Cycloalkylene group, unsubstituted or G ⁴ substituted C1~C6 alkylene C3~6 cycloalkylene group, unsubstituted or substituted by C ⁴ C1~C6 alkoxy C3~6 cycloalkyl, unsubstituted or substituted with G ⁴ of extending C4 ~ C6 cycloalkenyl group (cycloalkenylene group), or G ⁴ unsubstituted or substituted 3 to 6-membered extension of heterocyclic group (heterocyclylene group).

Further, ^a carbon atom of B ^a or ^{a part} of the substituent G ⁴ on B ^a may be bonded to a carbon atom on Ar ² to form a 5- to 6-membered ring.

* indicates the bonding position of the organic group represented by the formula (II) or the formula (III)]

G ¹ represents a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkyloxy group, a C1-6 alkyloxycarbonyl group, a methyloxy group, a C1-6 alkyloxy group, a C1~6 group. Alkoxycarbonyloxy, cyano, or halogen. When two or more of R ¹ , R ² , R ³ , R ⁴ or R ^{a is a} group substituted with G ¹ , the G ^{1 's} may be the same or different.

G ² represents a C1~6 alkyl group, a hydroxyl group C1~6 alkyl group, a C2~6 alkenyl group, a C2~6 alkynyl group, a C3~8 cycloalkyl group, a C1~6 halogenated alkyl group, a C1~6 alkoxy group C1~ 6 alkyl, C1~6 alkoxy C1~6 halogenated alkyl, C2-6 halogenated alkenyl, C2-6 halogenated alkynyl, hydroxy, C1-6 alkoxy, C3~8 cycloalkyl C1~6 alkane Oxy group, C1~6 alkoxy C1~6 alkoxy group, C1~6 halogenated alkoxy group, C1~6 halogenated alkoxy C1~6 halogenated alkoxy group, formyl group, C1~6 alkylcarbonyl group, C1 ~ 6 alkoxycarbonyl group, carboxylic acyl group, C1 ~ 6 alkylcarbonyloxy, C1 ~ 6 alkoxycarbonyl group, C1 ~ 6 alkoxycarbonyl group, unsubstituted or substituted with G ²¹ the C6 ~ 10 aryl group, unsubstituted or substituted with G ²¹ C6 ~ 10 aryl group of C1 ~ 6 alkyl, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryloxy, unsubstituted or G ²¹ Substituted 3-6 membered heterocyclic group, unsubstituted or substituted by G ²¹ 3-6 membered heterocyclic oxy group, C1~6 alkylthio group, C1-6 alkyl sulfinyl group, C1~6 alkyl group Sulfonyl, C1~6 halogenated alkylthio, C1~6 halogenated alkylsulfinyl, C1-6 halogenated alkylsulfonyl, pentafluorosulfanyl group, unsubstituted or substituted by G ²¹ the C6 ~ 10 aryl group, unsubstituted or substituted with G ²¹ C6 ~ 10 aryl methylsulfoximide acyl, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl sulfonic acyl group, a nitro group, a cyano group, a halogen group, C1 ~ 6 alkylene, C1 ~ 6 alkylene group Dioxy, or C1~6 halogenated alkyldioxy. When two or more of R ¹ , R ² , R ³ , R ⁴ , R ^a , G ⁴ , Ar ¹ or Ar ² are the above-mentioned groups substituted by G ² , the G ² may be the same as each other, or different.

G ²¹ represents a C1-6 alkyl group, a C1-6 alkyl halide, a C1-6 alkyloxy group, a C1-6 alkyl alkoxy group, or a halogen group. In the case where two or more of G ² or G ⁴ are the above-mentioned groups substituted by G ²¹ , the G ²¹ may be the same or different from each other.

G ⁴ represents a C1~6 alkyl group, a C3~8 cycloalkyl group, a C1~6 halogenated alkyl group, a C1~6 alkoxy C1~6 alkyl group, a C2~6 alkenyloxy C1~6 alkyl group, a hydroxyl group, a C1 group. ~ 6 alkoxy group, a C1 to C6 alkoxy group a C1 ~ 6 alkoxy, C2 ~ 6 alkenyl group, a C1 ~ 6 alkoxycarbonyl, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl group, an 3- to 6-membered heterocyclic group substituted by or substituted with G ²¹ , cyano group, halogen group, C1~6 alkylene group, C1~6 alkylenedioxy group, pendant oxy group, C3-8 cycloalkyl group C1 ~ 6 alkyl, unsubstituted or substituted with G ²¹ C6 ~ 10 aryl group of a C1 ~ 6 alkyl, unsubstituted or substituted with the G ^21-membered heterocyclic group having 3 to 6 a C1 ~ 6 alkyl, C3 ~ 8 cycloalkoxy group having a C1 to 6 alkyl, unsubstituted or substituted with G ²¹ C6 ~ 10 aryloxy group of a C1 to 6 alkyl, unsubstituted or substituted with the 3 G ²¹ ~ ~ 6-membered heterocyclic group having a C1 6 alkyl, C1 ~ 6 alkylene (alkylidene group), C1 ~ 6 alkoxyimino group, unsubstituted or substituted with G ²¹ C6 ~ 10 aryl group of C1 ~ 6 alkoxyimino group, or C1~6 alkyl fluorenyl]

[2] A bactericidal agent for agricultural and horticultural, comprising at least one selected from the group consisting of the compound of the above [1] and a salt thereof as an active ingredient.

[3] A pest control agent comprising at least one selected from the group consisting of the compound of the above [1] and a salt thereof as an active ingredient.

[4] An insecticidal or acaricidal agent comprising at least one selected from the group consisting of the compound of the above [1] and a salt thereof as an active ingredient.

The pyridine compound of the present invention is a novel compound which has the effects of pest control, sterilization, acaricidal killing, insecticidal action, and the like, does not cause phytotoxicity to plants, and has little toxicity to human or animal fish or has little influence on the environment. In particular, it exhibits excellent control effects against wheat diseases. Pyridine of the present invention The pyridine compound is useful as an active ingredient for agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.

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

[R ¹ ]

R ¹ represents a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 1-6 alkoxy group, an unsubstituted or G ² -substituted C 6 ～ 10 aryl group. a group, a 3 to 6 membered heterocyclic group, a cyano group or a halogen group.

The C1~6 alkyl group may be a straight chain, and if the carbon number is 3 or more, it may be a branched chain. Examples of the C1-6 alkyl group include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a second butyl group, an isobutyl group, a t-butyl group, a n-pentyl group, a n-hexyl group, and a different one. Butyl, neopentyl, 2-methylbutyl, 2,2-dimethylpropyl, isohexyl and the like.

Examples of the C1-6 alkoxy group include a methoxy group, an ethoxy group, a n-propoxy group, and a n-butoxy group. N-pentyloxy, n-hexyloxy, isopropoxy, isobutoxy, second butoxy, tert-butoxy, isohexyloxy and the like.

Examples of the C6-10 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, an anthracenyl group, a dihydroindenyl group, and a tetralinyl group.

The 3-6 membered heterocyclic group contains one to four hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a constituent atom of the ring. The heterocyclic group may be any of a monocyclic ring and a polycyclic ring. If at least one of the polycyclic heterocyclic groups is a heterocyclic group, the remaining ring may be any of a saturated alicyclic ring, an unsaturated alicyclic ring or an aromatic ring. Examples of the 3-6 membered heterocyclic group include a 3 to 6 membered saturated heterocyclic group, a 5 to 6 membered heteroaryl group, and a 5 to 6 membered partially unsaturated heterocyclic group.

Examples of the 3-6 membered saturated heterocyclic group include aziridine group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, and tetrahydrofuranyl group. , tetrahydrothiazolyl, piperidinyl, piperidine base, A phenyl group, a tetrahydropyranyl group, a dioxolanyl group, a dioxanyl group, or the like.

Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, and a pyrazolyl group. Azolyl, different Azyl, thiazolyl, isothiazolyl, triazolyl, A oxazolyl group, a thiadiazolyl group, a tetrazolyl group or the like.

As a 6-membered heteroaryl group, a pyridyl group or a pyridyl group is exemplified. Base, pyrimidinyl, oxime Base, three Base.

Examples of the halogen group include a fluorine group, a chlorine group, a bromine group, and an iodine group.

The substituent G ¹ represents a hydroxyl group, a C1-6 alkoxy group, a C1-6 alkoxy C1-6 alkyloxy group, a C1-6 alkoxycarbonyl group, a methyloxy group, a C1-6 alkyloxy group, a C1 group. ~6 alkoxycarbonyloxy, cyano, or halogen. Further, when two or more of R ¹ , R ² , R ³ , R ⁴ or R ^a are ^a group substituted by G ¹ , the G ¹ may be the same or different from each other.

The C1~6 alkoxy group and the halogen group in the substituent G ¹ are as described above.

Examples of the C1-6 alkoxy C1-6 alkyloxy group include a methoxymethoxy group and a methoxyethoxy group.

Examples of the C1-6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an isopropoxycarbonyl group, and a third butoxycarbonyl group.

Examples of the C1-6 alkyloxycarbonyl group include an ethoxycarbonyl group, a propenyloxy group, and a butoxy group.

Examples of the C1-6 alkoxycarbonyloxy group include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, a n-propoxycarbonyloxy group, an isopropoxycarbonyloxy group, and a n-butoxycarbonyloxy group. A group, a third butoxycarbonyloxy group or the like.

The substituent G ² represents a C1-6 alkyl group, a hydroxy C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3~8 cycloalkyl group, a C1~6 halogenated alkyl group, a C1~6 alkoxy group. C1~6 alkyl, C1~6 alkoxy C1~6 halogenated alkyl, C2-6 halogenated alkenyl, C2-6 halogenated alkynyl, hydroxyl, C1-6 alkoxy, C3~8 cycloalkyl C1~ 6 alkoxy group, C1~6 alkoxy C1~6 alkoxy group, C1~6 halogenated alkoxy group, C1~6 halogenated alkoxy C1~6 halogenated alkoxy group, formyl group, C1~6 alkyl group Carbonyl, C1-6 alkyloxycarbonyl, methyloxy, C1-6 alkylcarbonyloxy, C1-6 alkyloxycarbonyl, C1-6 alkyloxycarbonyl, unsubstituted or via G the ^{21-substituted} C6 ~ 10 aryl group, unsubstituted or substituted with G ²¹ C6 ~ 10 aryl group of C1 ~ 6 alkyl, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryloxy, unsubstituted or G ²¹ substituted 3-6 member heterocyclic group, unsubstituted or G ²¹ substituted 3-6 membered heterocyclicoxy group, C1-6 alkylthio group, C1-6 alkyl sulfinylene group, C1~6 Alkyl sulfonyl, C1~6 halogenated alkylthio, C1-6 halogenated alkyl sulfinylene, C1-6 halogenated alkylsulfonyl, pentafluorothio, unsubstituted or substituted by G ²¹ ~10 arylthio group, unsubstituted or substituted by G ²¹ C6~10 aryl sulfin Mercapto, unsubstituted or substituted by G ²¹ C6-10 sulfonyl, nitro, cyano, halo, C1-6 alkyl, C1-6 alkyl dioxy, or C1~ 6 Halogenated alkyldioxy.

C1~6 alkyl group, C1~6 alkoxy group, C1~6 alkoxy C1~6 alkoxy group, C1~6 alkoxycarbonyl group, C1~6 alkylcarbonyloxy group, C1 in the substituent G ² The ~6 alkoxycarbonyloxy group, the C6~10 aryl group, the 3-6 membered heterocyclic group and the halogen group are as described.

Examples of the hydroxy C1-C6 alkyl group include a methylol group, a hydroxyethyl group, and a hydroxypropyl group.

Examples of the C2-6 alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl (allyl) group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, and a 1-methyl group. 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and the like.

Examples of the C2-6 alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, and a 1-methyl-2- group. Propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl, 1,1-dimethyl-2-butynyl and the like.

Examples of the C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a 2-adamantyl group.

The C1~6 alkoxy C1-6 alkyl group is substituted with the above C1~6 alkoxy group on the C1~6 alkyl group described above. Examples of the C1-6 alkoxy C1-6 alkyl group include a methoxymethyl group, an ethoxymethyl group, a methoxyethyl group, an ethoxyethyl group, a methoxy-n-propyl group, and an ethoxy group. A Base, ethoxyethyl, n-propoxymethyl, isopropoxyethyl, second butoxymethyl, tert-butoxyethyl and the like.

The C3-8 cycloalkyl C1~6 alkoxy group is substituted with the above C3-8 cycloalkyl group on the C1~6 alkoxy group described above. Examples of the C3-8 cycloalkyl C1-6 alkoxy group include a cyclopropylmethoxy group, a cyclobutylmethoxy group, a cyclopentylmethoxy group, a cyclohexylmethoxy group, and a 2-(cyclopropyl group)- Ethoxylate and the like.

The C1~6 alkylcarbonyl group is bonded to the carbonyl group having the above C1~6 alkyl group. Examples of the C1-6 alkyloxycarbonyl group include an ethyl fluorenyl group, a propyl fluorenyl group, a butyl fluorenyl group, an isobutyl fluorenyl group, and a trimethyl acetyl group.

The C1-6 alkoxycarbonylamino group is substituted on the amine group with the C1-6 alkoxycarbonyl group described. Examples of the C1-6 alkoxycarbonylamino group include a methoxycarbonylamino group, an ethoxycarbonylamino group, a n-propoxycarbonylamino group, an isopropoxycarbonylamino group, and a n-butoxycarbonylamine. A group, a third butoxycarbonylamino group or the like.

The C6~10 aryl C1-6 alkyl group is substituted with the above C6~10 aryl group on 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 substituted with a C6~10 aryl group as described above on the hydroxyl group. Examples of the C6-10 aryloxy group include a phenoxy group and a naphthyloxy group.

The 3-6 membered heterocyclic oxy group is substituted with a 3-6 membered heterocyclic group on the hydroxy group. Examples of the 3-6 membered heterocyclic oxy group include a pyrazolyloxy group and a pyridyloxy group. The 3-6 membered heterocyclic oxy group is preferably a 5-6 membered heterocyclic oxy group.

The C1~6 alkylthio group is substituted with a C1~6 alkyl group on the SH group. Examples of the C1-6 alkylthio group include a methylthio group, an ethylthio group, a n-propylthio group, a n-butylthio group, a n-pentylthio group, a n-hexylthio group, and the like. Isopropylthio, isobutylthio and the like.

The C1~6 alkylsulfinyl group is substituted with a C1~6 alkyl group on the sulfinylene group. Examples of the C1-6 alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, and a tert-butylsulfinyl group.

The C1~6 alkylsulfonyl group is a C1~6 alkyl group bonded to a sulfonyl group. Examples of the C1-6 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, and a tert-butylsulfonyl group.

The C6~10 arylthio group is substituted with a C6~10 aryl group on the SH group. Examples of the C6-10 arylthio group include a phenylthio group and a naphthylthio group.

The C6~10 arylthio group is substituted with a C6~10 aryl group on a sulfanyl group. Examples of the C6-10 arylthio group include a phenylthio group and a naphthylthio group.

The C6~10 arylsulfinyl group is substituted with a C6-10 aryl group on the sulfinylene group. Examples of the C6-10 arylsulfinyl group include a phenylsulfinyl group and a naphthylsulfinyl group.

The C6~10 arylsulfonyl group is substituted with a C6-10 aryl group on the sulfonyl group. Examples of the C6-10 arylsulfonyl group include a phenylsulfonyl group and a naphthylsulfonyl group.

The C1~6 alkylene group is a divalent group obtained by removing two hydrogen atoms of the C1-6 alkane. Examples of the C1-6 alkylene group include a methylene group, an ethylidene group (dimethylene group), a trimethylene group, a tetramethylene group, and a propane-1,2-diyl group (i.e., a propyl group).

The C1~6 alkylenedioxy group is a divalent group obtained by substituting two hydrogen atoms of a C1-6 alkane with an oxy group. Examples of the C1~6 alkylenedioxy group include a methylenedioxy group (-OCH ₂ O-), an extended ethylene dioxy group (-OCH ₂ CH ₂ O-), and a trimethylene dioxy group. Wait. Examples of the C6-10 aryl group substituted by a C1~6 alkylenedioxy group as G ² include 2,3-dihydro-benzo[1,4]dioxy and benzo[1,3. Dioxinyl and the like.

C1~6 halogenated alkyl group, C2-6 halogenated alkenyl group, C2~6 halogenated alkynyl group, C1~6 halogenated alkoxy group, and C1~6 halogenated alkylenedioxy group are described in the C1~6 alkyl group. And a C2-6 alkenyl group, a C2~6 alkynyl group, a C1~6 alkoxy group, and a C1~6 alkylenedioxy group are substituted with a halogen group.

Examples of the C1-6 halogenated alkyl group include a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, a trichloromethyl group, and a tribromo group. Methyl, 1-chloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 4-fluorobutyl, 4-chlorobutyl, 3, 3,3-Trifluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, perfluorohexyl, perchlorohexyl, 2,4,6-trichlorohexyl, and the like.

Examples of the C2-6 halogenated alkenyl group include a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group.

Examples of the C2-6 halogenated alkynyl group include a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, and a 5-bromo-2-pentynyl group.

Examples of the C1-6 halogenated alkoxy group include a chloromethoxy group, a dichloromethoxy group, a difluoromethoxy group, a trichloromethoxy group, a trifluoromethoxy group, and a 1-fluoroethoxy group. 1-difluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, 2,2,3,4,4, 4-hexafluorobutoxy, 1-bromo-1,1,2,2-tetrafluoroethoxy, and the like.

Examples of the C1-6 halogenated alkylenedioxy group include difluoromethylenedioxy (-OCF ₂ O-) and tetrafluoroethylideneoxy (-OCF ₂ CF ₂ O-). As warp ² as the halogenated C1 ~ 6 alkyl substituted with two projecting G group of C6 ~ 10 aryl group, include: 2,2,3,3-tetrafluoro-2,3-dihydro - benzo [1, 4] Dioxy, 2,2-difluoro-benzo[1,3]dioxanyl and the like.

C1~6 alkoxy C1~6 halogenated alkyl, C1~6 halogenated alkoxy C1~6 halogen Alkoxy group, C1~6 halogenated alkylthio group, C1~6 halogenated alkyl sulfinylene group, and C1~6 halogenated alkylsulfonyl group are described in the C1~6 alkoxy C1~6 alkyl group. And a C1~6 alkoxy C1~6 alkoxy group, a C1~6 alkylthio group, a C1-6 alkyl sulfinyl group, and a C1~6 alkylsulfonyl group substituted with a halogen group.

Examples of the C1-6 alkoxy C1~6 halogenated alkyl group include difluoro(methoxy)methyl and 1,1,1,3,3,3-hexafluoro-2-methoxypropane-2. - Base, etc.

Examples of the C1-6 halogenated alkoxy C1~6 halogenated alkoxy group include difluoro(methoxy)methoxy and 1,2,2-trifluoro-2-(trifluoromethoxy)ethoxylate. Base.

Examples of the C1-6 halogenated alkylthio group include a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.

Examples of the C1-6 halogenated alkylsulfinyl group include a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.

Examples of the C1-6 halogenated alkylsulfonyl group include a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.

The substituent G ²¹ represents a C1-6 alkyl group, a C1-6 alkyl halide, a C1-6 alkyloxy group, a C1-6 alkyl alkoxy group, or a halogen group. These are as already stated.

In the case where two or more of G ² or G ⁴ are the above-mentioned groups substituted by G ²¹ , the G ²¹ may be the same or different from each other.

In the present invention, R ^{1 is} preferably a hydrogen atom, an unsubstituted or G ¹ -substituted C1-6 alkyl group (preferably unsubstituted), unsubstituted or substituted with G ¹ alkoxy group. (preferably unsubstituted), unsubstituted or substituted by G ² (preferably C1-6 alkoxy, C1-6 alkoxycarbonyloxy) C6~10 aryl (preferably phenyl) a 6-membered heteroaryl group (preferably unsubstituted pyridyl), a cyano group or a halogen group which is unsubstituted or substituted by G ² , more preferably an unsubstituted C 1-6 alkyl group or a halogen base.

[R ² and R ³ ]

R ² and R ³ each independently represent a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 3 -8 cycloalkyl group, unsubstituted or via G ¹ the substituted C1 ~ 6 alkoxy, methyl acyl, carboxylic acyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl carbonyl, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl carbonyloxy a C6-10 aryl group which is unsubstituted or substituted by G ² , (unsubstituted or substituted by a G ¹ C1-6 alkoxyimino group)-C1~6 alkyl group, a cyano group, or a halogen group .

C1~6 alkyl group, C3~8 cycloalkyl group, C1~6 alkoxy group, C1-6 alkyloxy group, C1-6 alkyloxy group, C6~10 aryl group, halogen in R ² and R ³ The groups and the substituents G ¹ and G ² are as described.

Examples of the (C1-6 alkoxyimino)-C1-6 alkyl group include a methoxyiminomethyl group and a 1-(ethoxyimino)-ethyl group.

R ¹ and R ² may together form a 5-6 member ring together with the carbon atoms bonded to each of R ¹ and R ² . Examples of the 5-6 member ring include a cyclopentene ring and a cyclohexene ring.

In the present invention, R ^{2 is} preferably a hydrogen atom, unsubstituted or G ¹ (preferably a hydroxyl group, a halogen group, a C1-6 alkoxy group, a C1-6 alkyloxy group, a C1~6). alkoxycarbonyl group) substituted with the C1 ~ 6 alkyl, unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxy group (preferably unsubstituted), unsubstituted or G ² (preferably the substituted C1 ~ 6 alkoxy) C6 ~ 10 aryl group (preferably phenyl), unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl-carbonyl group (preferably unsubstituted), (unsubstituted Or a C1~6 alkoxyimino)-C1~6 alkyl group (preferably unsubstituted), a halogen group, a cyano group, a formyl group, and more preferably an unsubstituted C1~ substituted by G ¹ . 6 alkyl.

In the present invention, as R ³ , it is preferably unsubstituted or G ¹ (preferably a hydroxyl group, a halogen group, a C1-6 alkoxy group, a C1-6 alkyloxy group, a C1-6 alkoxy group). carbonyloxy) substituent of C1 ~ 6 alkyl, unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxy group (preferably unsubstituted), C3 ~ 8 non-substituted cycloalkyl group (preferably 3~4 cycloalkyl), unsubstituted or substituted by G ¹ C1-6 alkylcarbonyloxy (preferably unsubstituted), unsubstituted or substituted by G ² C6~10 aryl (more Preferred as unsubstituted phenyl), (unsubstituted or substituted by C ¹ C1~6 alkoxyimino)-C1~6 alkyl (preferably unsubstituted), halogen, cyano Or a mercapto group, more preferably unsubstituted or substituted by G1 (preferably hydroxy, halo, C1-6 alkoxy, C1-6 alkyloxycarbonyl, C1-6 alkoxycarbonyloxy) C1~6 alkyl or halogen.

[R ⁴ ]

R ⁴ represents a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 2 -6 alkenyl group, an unsubstituted or G ¹ -substituted C 2 -6 alkynyl group. , unsubstituted or substituted by G ¹ C 3-8 cycloalkyl, unsubstituted or G ² substituted C 6-10 aryl C 1-6 alkyl, unsubstituted or substituted by G ² 3-6 members heterocyclyl, unsubstituted or substituted with G ² of the 3 to 6-membered heterocyclic group a C1 to 6 alkyl, methyl acyl, unsubstituted or substituted with G ¹ of a C1 to 6 alkyl carbonyl, unsubstituted or G ¹ via the C3 ~ 8 cycloalkyl substituted alkylcarbonyl, unsubstituted or substituted with G ¹ group of C1 ~ 6 alkenyl carbonyl group, unsubstituted or substituted with G ² of the C6 ~ 10 aryl-carbonyl group, an unsubstituted or G ¹ -substituted alkoxycarbonyl group substituted by G ¹ , unsubstituted or substituted C 2 6 alkenyloxycarbonyl group by G ¹ , unsubstituted or substituted C ¹ 6 alkylsulfonyl group by G ¹ , unsubstituted or ^one of C1 ~ 6 alkyl substituted aminocarbonyl through G, unsubstituted or substituted with ¹ G of (C1 ~ 6 alkylthio) carbonyl, unsubstituted or substituted with ¹ G of C1 ~ 6 alkyl group (thiocarbonyl) or a group represented by the formula (IV).

Of R ^{4 is} a C1 to 6 alkyl, C2 to 6 alkenyl, C2 to 6 alkynyl group, C3 ~ 8 cycloalkyl group, C6 ~ 10 aryl group a C1 to 6 alkyl, 3 to 6-membered heterocyclic group, a C1 ~ 6 alkylcarbonyl group, C1 ~ 6 alkoxycarbonyl, C1 ~ 6 alkylsulfonyl group, a substituted substituent groups G ¹ and G ² as already described were based.

The 3-6 membered heterocyclic C1~6 alkyl group is substituted with a 3-6 membered heterocyclic group on the C1~6 alkyl group. The 3-6 membered heterocyclic group C1-6 alkyl group is preferably a tetrahydrofuranylmethyl group, a tetrahydropyranylmethyl group, a dioxolylmethyl group or a dioxanylmethyl group. ~6 member saturated heterocyclic group C1~6 alkyl; pyrazolylmethyl, pyridylmethyl and the like 5~6 member heteroaryl C1~6 alkyl group.

The C3-8 cycloalkylcarbonyl group is bonded to the carbonyl group having the C3-8 cycloalkyl group described above. Examples of the C3-8 cycloalkylcarbonyl group include a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, and a cyclohexylcarbonyl group.

As the C6-10 arylcarbonyl group, a C6-10 aryl group is bonded to a carbonyl group. Examples of the C6-10 arylcarbonyl group include a benzamidine group and the like.

Examples of the C2-6 alkenylcarbonyl group include an acryloyl group and a methacryloyl group.

Examples of the C2-6 alkenyloxycarbonyl group include a vinyloxycarbonyl group, a 1-propenyloxycarbonyl group, and a 2-propenyloxycarbonyl group (allyloxycarbonyl group).

Examples of the C1-6 alkylaminocarbonyl group include a methylaminocarbonyl group and a dimethylaminocarbonyl group.

Examples of the (C1-6 alkylthio)carbonyl group include a (methylthio)carbonyl group and an (ethylthio)carbonyl group.

Examples of the C1-6 alkylamino group (thiocarbonyl group) include a methylamino group (thiocarbonyl group) and a dimethylamino group (thiocarbonyl group).

[In the formula (IV), G ^a each independently represents a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 2 -6 alkenyl group, unsubstituted or substituted by G ¹ group of C2 ~ 6 alkynyl, unsubstituted or substituted with G ¹ of C3 ~ 8 cycloalkyl, or unsubstituted or substituted G ² of the C6 ~ 10 aryl group.

G ^b represents a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 2 -6 alkenyl group, an unsubstituted or G ¹ -substituted C 2 -6 alkynyl group. , unsubstituted or substituted with G ¹ of C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ² of the C6 ~ 10 aryl group, or an unsubstituted or substituted G ² of the 3 to 6-membered heterocyclic group.

T represents an oxygen atom, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio)carbonyl group, a carbonyl group (thio group), a (thio)carbonyloxy group, an oxycarbonyl group (thio group), Or formula: -OC(=O)-N(G ^b )-.

* indicates the bonding position of the base represented by the formula (IV)]

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

In the present invention, R ^{4 is} preferably a hydrogen atom, unsubstituted or substituted by G ¹ (preferably a C1-6 alkyloxycarbonyl group, a C1-6 alkoxycarbonyloxy group, a halogen group). C1 ~ 6 alkyl, the unsubstituted or substituted by G ¹ C2 ~ 6 alkenyl group (preferably unsubstituted), a substituted or unsubstituted by G ² (preferably C1 ~ 6 alkoxy) of C6 10 ~ C1 ~ 6 alkyl aryl group (preferably a benzyl group), an unsubstituted or G ¹ (preferably C1 ~ 6 alkoxy, C1 ~ 6 alkyl-carbonyloxy) of C1 ~ 6 alkoxy substituted with carbonyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxycarbonyl group (preferably unsubstituted), unsubstituted or substituted with G ¹ of C2 ~ 6 alkenyl-carbonyl group (preferably unsubstituted ), unsubstituted or substituted with G ¹ group of C1 ~ 6 alkyl-carbonyl group (preferably unsubstituted), unsubstituted or substituted with G ¹ of (C1 ~ 6 alkylthio) carbonyl group (preferably Unsubstituted), unsubstituted or heterocyclic group substituted by G ² (preferably hydroxy, hydroxy C 1-6 alkyl) (preferably 3 to 6 membered saturated heterocyclic group), more preferably a hydrogen atom, unsubstituted or G ¹ (preferably C1 ~ 6 alkylcarbonyloxy, C1 ~ 6 alkoxycarbonyl group) substituted with the C1 ~ 6 alkyl, unsubstituted or G ¹ (preferably C1 ~6 alkoxy C1 ~ 6 alkyl-carbonyloxy) of C1 ~ 6 alkyl substituted with a carbonyl group, or G ¹ unsubstituted or substituted with the C1 ~ 6 alkoxycarbonyl group.

[Q]

Q represents any one of the organic groups represented by the formula (II) or the formula (III). Further, * represents a bonding position of an organic group represented by the formula (II) or the formula (III).

<R ^a 〉

R ^a represents a hydrogen atom, an unsubstituted or G ¹ -substituted C 1-6 alkyl group, an unsubstituted or G ¹ -substituted C 3 -8 cycloalkyl group, an amine group, a C 1-6 alkylcarbonylamino group, or C6~10 aryl group which is unsubstituted or substituted by G ² .

R ^a in the C1 ~ 6 alkyl, C3 ~ 8 cycloalkyl group, C6 ~ 10 aryl group, a substituted the substituent group G ¹ and G ² as already described were based.

The C1~6 alkylcarbonylamino group is substituted on the amine group with the C1~6 alkylcarbonyl group described. Examples of the C1-6 alkyloxycarbonyl group include an ethyl hydrazino group and a propyl hydrazino group.

In the present invention, as R ^a , a hydrogen atom, an unsubstituted alkyl group, an unsubstituted C 3-8 cycloalkyl group (preferably a C 3 ～ 4 cycloalkyl group), an amine group, and a C 1 -6 are preferable. An alkylcarbonylamino group, a C6-10 aryl group (preferably a phenyl group) which is unsubstituted or substituted with G ² (preferably a C1-6 alkyl halide), more preferably an unsubstituted alkyl group or hydrogen atom.

<Ar ¹ 〉

Ar ¹ represents an unsubstituted or substituted G ² of C6 to 10 aryl group, or an unsubstituted or substituted G ² of the 3 to 10-membered heterocyclic group.

The C6-10 aryl group in Ar ¹ and the substituent G ² are as described above.

The 3 to 10 membered heterocyclic group contains a ring-shaped group of one to four hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a constituent atom of the ring. The heterocyclic group may be any of a monocyclic ring and a polycyclic ring. If at least one of the polycyclic heterocyclic groups is a heterocyclic group, the remaining ring may be any of a saturated alicyclic ring, an unsaturated alicyclic ring or an aromatic ring. Examples of the 3 to 10 membered heterocyclic group include a 3 to 10 membered saturated heterocyclic group, a 5 to 10 membered heteroaryl group, and a 5 to 6 membered partially unsaturated heterocyclic group.

Examples of the 3 to 10 membered saturated heterocyclic group include a 3-membered saturated heterocyclic group such as an aziridine group or an oxiranyl group; and a 4-membered saturated heterocyclic group such as azetidinyl or oxetanyl; 5-membered saturated heterocyclic group such as pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiazolyl, imidazolidinyl, pyrazolylyl, dioxolyl; piperidinyl, piperidine base, a 6-membered saturated heterocyclic group such as a phenyl group, a tetrahydropyranyl group or a dioxanyl group;

Examples of the 5- to 10-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, and a pyrazolyl group. Azolyl, different Azyl, thiazolyl, isothiazolyl, triazolyl, 5-membered heteroaryl group such as oxazolyl, thiadiazolyl, tetrazolyl; pyridyl, pyridyl Base, pyrimidinyl, oxime Base, three 6-membered heteroaryl; fluorenyl, isodecyl, benzofuranyl, carbazolyl, benzo Azolyl, benzopyrene 9-membered heteroaryl group such as azolyl, benzothiazolyl, benzisothiazolyl; quinolyl, isoquinolinyl, Olinyl group, hydrazine Base, quinazolinyl, quin 10-membered heteroaryl group such as phenyl group;

Examples of the 5- to 6-membered partially unsaturated heterocyclic group include a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, and a pyrazolinyl group. 5-membered partially unsaturated heterocyclic group such as oxazoline group; a 6-membered partially unsaturated heterocyclic group such as an oxazoline group or a dihydropyranyl group;

The 3 to 10 membered heterocyclic group in Ar ¹ is preferably a 5- to 10-membered heteroaryl group such as pyrazolyl, pyridyl, pyrimidinyl or quinolyl.

In the present invention, Ar ^{1 is} preferably an unsubstituted or G ² -substituted C 6-10 aryl group (preferably phenyl, naphthyl) or an unsubstituted or G ² substituted 5-6 member heteroaryl. The group (preferably pyridyl) is 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 preferably a C1~6 alkyl group, a C1~6 halogenated alkyl group, a C1~6 alkoxy group, a C1~6 alkoxy C1~6 halogenated alkyl group, a C1~6 halogenated alkoxy group, C1 ~ 6 alkoxycarbonyl, unsubstituted or G ²¹ (preferably halogenated C1 ~ 6 alkyl) substituted with the C6 ~ 10 aryl group (preferably phenyl), unsubstituted or G ²¹ (more C6~10 aryl C1~6 alkyl (preferably benzyl) substituted, C6 substituted by G ²¹ (preferably C1~6 halogenated alkyl) ~10 aryloxy (preferably phenoxy), C1~6 halogenated alkylthio, C1~6 halogenated alkyl sulfinylene, C1~6 halogenated alkylsulfonyl, pentafluorothio, un unsubstituted or G ²¹ (preferably halogenated C1 ~ 6 alkyl) substituted with the C6 ~ 10 aryl group (preferably phenyl group), an unsubstituted or G ²¹ (preferably a halogenated alkyl group of C1 ~ 6 ) substituted aryl of C6 ~ 10 acyl alkylsulfinyl (preferably sulfonylurea phenyl group), unsubstituted or G ²¹ (preferably halogenated C1 ~ 6 alkyl) C6 ~ 10 aryl group of the sulfonyl Sulfhydryl (preferably phenylsulfonyl), nitro, C1~6 halogenated alkyldioxy and/or halogen, more preferably C1~6 alkyl, C1~6 halogenated alkyl, C1~ 6 Halogenated alkoxy, unsubstituted or via G ²¹ (preferably C1) The ~6 halogenated alkyl group is substituted with a C6-10 aryloxy group (preferably a phenoxy group) and/or a halogen group.

<Ar ² 〉

Ar ² represents an unsubstituted or G ² -substituted C 6 -10 aryl group, an unsubstituted or G ² -substituted C 6 -10 aryloxy group, an unsubstituted or G ² -substituted C 6 -10 arylthio group, Unsubstituted or G ² substituted C6-10 sulfinyl, unsubstituted or G ² substituted C6-10 sulfonyl, unsubstituted or substituted by G ² 3~10 members Heterocyclic group, unsubstituted or G ² substituted 3-10 membered heterocyclic oxy group, unsubstituted or G ² substituted 3-6 membered heterocyclic thio or ferrocene group.

The C6-10 aryl group in Ar ² is preferably a phenyl group as described above.

The C6-10 aryloxy group is preferably a phenoxy group as described above.

The 3 to 10 membered heterocyclic group is as described, preferably a 5 to 10 membered ring heteroaryl group, more preferably a thiazolyl group, a triazolyl group, a pyrazolyl group, a pyridyl group or a fluorene group. Base, quinolyl.

The 3 to 10 membered heterocyclic oxy group is substituted with a 3 to 10 membered heterocyclic group on the hydroxy group. The 3- to 10-membered heterocyclic oxy group is preferably a 5- to 6-membered saturated heterocyclic oxy group or a 5- to 6-membered heteroaryloxy group.

As a 5- to 6-membered heteroaryloxy group, more preferably pyrazolyloxy, pyridyloxy or fluorene Oxyl, pyrimidinyloxy.

The 3 to 10 membered heterocyclic thio group is substituted with a 3 to 10 membered heterocyclic group on the SH group. Examples of the 3 to 10 membered heterocyclic thio group include a 5- to 6-membered heteroarylthio group such as a pyrazolylthio group and a pyridylthio group, and a pyridylthio group is preferred.

The C6-10 arylthio group is as described above, preferably a phenylthio group.

The arylsulfinyl group is preferably a phenylsulfinylene group as described above.

The arylsulfonyl group is preferably a phenylsulfonyl group as described above.

The substituent G ² is as described above, preferably a C1-6 alkyl group, a C1-6 alkyl halide, a C1-6 alkyloxy group, a C3-8 cycloalkyl C1-6 alkyl group (preferably C3). 1-4 cycloalkyl-alkoxy), C1 ~ 6 halogenated alkoxy, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl group (preferably phenyl), unsubstituted or substituted with the C6 G ²¹ ~10 aryloxy (preferably phenoxy), unsubstituted or substituted by G ²¹ 5-6 membered heterocyclic group (preferably pyridyl), unsubstituted or substituted by G ²¹ 5~6 A heterocyclic oxy group (preferably a pyridyloxy group), a pentafluorothio group, a cyano group, a halogen group, or a C1~6 halogenated alkylenedioxy group.

As G ^2, more preferably represents a halogenated C1 ~ 6 alkyl, C1 ~ 6 alkoxy group, a halogenated C1 ~ 6 alkoxy, unsubstituted or substituted with G ²¹ of phenyl, unsubstituted or substituted by G ²¹ a phenoxy group, an unsubstituted or G ²¹ -substituted pyridyl group, an unsubstituted or G ²¹ -substituted pyridyloxy group, a halogen group, or a C1~2 halogenated alkylenedioxy group.

The substituent G ²¹ is preferably a halogen group, a C1 to 6 halogenated alkyl group or a C1 to 6 halogenated alkoxy group, as described above.

In these, as Ar ^2, preferably unsubstituted or substituted with G ² of the C6 ~ 10 aryl group (preferably phenyl), unsubstituted or substituted by the G ² C6 ~ 10 aryloxy group (more Preferably, the phenoxy group, the unsubstituted or G ² substituted 3-10 membered heterocyclic group (preferably thiazolyl, triazolyl, pyrazolyl, pyridyl, fluorene) a 3- to 10-membered heterocyclic oxy group (preferably pyridyloxy, pyridine, unsubstituted or substituted by G ² ) Oxyl, pyrimidinyloxy).

Further, as G ² , a C1-6 halogenated alkyl group, a C1-6 halogenated alkoxy group, or a halogen group is more preferable.

<B ^a 〉

B ^a represents an unsubstituted or G ⁴ -substituted C 1 -C 6 alkylene group, an unsubstituted or G ⁴ -substituted C 2 -C 6 alkenyl group, an unsubstituted or G ⁴ -substituted C 2 -C 6 alkynyl group Unsubstituted or substituted by G ⁴ C1~C6 alkoxy C1~6 alkyl, unsubstituted or G ⁴ substituted C3~C6 cycloalkyl, unsubstituted or substituted by G ⁴ C1~C6 alkylene C3~6 cycloalkyl, unsubstituted or G ⁴ substituted C1~C6 alkoxy C3~6 cycloalkyl, unsubstituted or substituted by G ⁴ C4~C6 A cycloalkenyl group, or a 3 to 6 membered heterocyclic group which is unsubstituted or substituted with G ⁴ .

The C1~C6 alkylene group in B ^a is as described.

The C2~C6 extended alkenyl group is a divalent group obtained by removing two hydrogen atoms in the C2~C6 olefin. Examples of the C2-C6 alkenyl group include a vinyl group, a propylene group, and a butenyl group.

The C2~C6 alkynyl group is a divalent group obtained by removing two hydrogen atoms in the C2~C6 alkyne. Examples of the C2 to C6 alkynyl group include an ethynyl group, a propargyl group, and a butynyl group.

The C1~C6 alkoxy group C1~6 alkyl group is a group in which two C1~6 alkyl groups are bonded via an oxygen atom. Examples of the C1 to C6 alkoxy C1~6 alkylene group include a methyleneoxymethylene group, a methyleneoxyethyl group, and an ethoxymethylene group.

The C3~C6 cycloalkyl group is a divalent group obtained by removing two hydrogen atoms of the C3~C6 cycloalkane. Examples of the C3 to C6 cycloalkylene group include a cyclopropyl group (1,2-cyclopropyl group), a cyclobutene butyl group (1,2-cyclopentene butyl group, or a 1,3-cyclopentylene group). ), a cyclopentyl group (1,2-cyclopentyl, or a 1,3-cyclopentyl), a cyclohexyl group (1,2-cyclohexylene, 1,3-cyclohexylene, or 1, 4-cyclohexyl), etc., preferably a cyclopentyl group or a cyclohexyl group.

The C1~C6 alkylene C3~6 extended cycloalkyl group is a group of C1~6 alkylene groups bonded to a C3~6 extended cycloalkyl group.

As a C1~C6 alkylene C3~6 cycloalkylene group, preferably a methylene cyclopropyl group, a methyleneoxycyclohexyl group, an exoethoxycyclohexyl group, etc., a C1~2 alkylene group C3~6 Cycloalkyl.

The C1~C6 alkoxy group C3~6 cycloalkylene group C1~6 alkylene group and the C3~6 cycloalkyl group are bonded via an oxygen atom. As the C1~C6 alkoxy C3~6 cycloalkyl group, preferably a methyleneoxycyclopropyl group, a methyleneoxycyclohexyl group, an exoethoxy extended cyclohexyl group, etc. C1~2 alkoxy group C3~ 6 cycloalkyl group.

The C4~C6 cycloalkenyl group is a divalent group obtained by removing two hydrogen atoms of the C3~C6 cyclic olefin. Examples of the C4 to C6 cycloalkenyl group include a cyclobutenyl group (1,2-cyclobutene). Base, 1,3-cyclobutenyl, 1,3-cyclobutenyl, or 3,4-cyclobutenyl), cyclopentenyl (1,2-cyclopentenyl, 1,3-cyclopentenyl, 1,4-cyclopentenyl, or 1,5-cyclopentenyl), cyclohexenylene (1,2-cyclohexenyl, 1, 3-cyclohexenylene, 1,4-cyclohexenyl), etc., preferably a cyclopentenyl group or a cyclohexene group.

The 3-6 member of the heterocyclic group is a divalent group obtained by removing two hydrogen atoms in the heteroalicyclic compound. The heteroalicyclic compound is a non-aromatic compound containing one to four hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a constituent atom of the ring.

Examples of the 3- to 6-membered heterocyclic group include a 3 to 6-membered saturated heterocyclic group or a 5- to 6-membered partially unsaturated heterocyclic group.

Examples of the heterocyclic group of 3 to 6 members include a dihydrofuranyl group, a tetrahydrofuranyl group, a pyrrolidino group, a pyrrolidinyl group, a pyrazolinyl group, a pyrazolyl group, an imidazolinyl group, and a stretching group. Imidazolidinyl Oxazoline Zyridinyl, thiazolinyl, thiazolidinyl, isoprene Zyridinyl, isothiazolidinyl, dihydropyranyl, tetrahydropyranyl, piperidinyl, piperazine Base Orolinic group and the like.

In the above, as the 3 to 6 membered heterocyclic group, it is preferably a 5- to 6-membered saturated heterocyclic group, and particularly preferably a piperidinyl group.

Furthermore, in a specific embodiment, the 3-6 membered heterocyclic group may also be crosslinked by a C1~6 alkylene group.

In the above, B ^{a is} preferably an unsubstituted or G ⁴ -substituted C 1 -C 6 alkylene group, an unsubstituted or G ⁴ -substituted C 2 -C 6 alkenyl group, unsubstituted or substituted by G ⁴ C2 ~ C6 alkynyl group extension, unsubstituted or substituted with G ⁴ of C3 ~ C6 cycloalkyl stretch, or G ⁴ unsubstituted or substituted 3 to 6-membered extension of heterocyclyl, more preferably is unsubstituted or G ⁴ was substituted with the C1 ~ C6 alkylene, unsubstituted or substituted with G ⁴ of C3 ~ C6 cycloalkyl stretch.

G ⁴ represents a C1~6 alkyl group, a C3~8 cycloalkyl group, a C1~6 halogenated alkyl group, a C1~6 alkoxy C1~6 alkyl group, a C2~6 alkenyloxy C1~6 alkyl group, a hydroxyl group, a C1 group. ~ 6 alkoxy group, a C1 to C6 alkoxy group a C1 ~ 6 alkoxy, C2 ~ 6 alkenyl group, a C1 ~ 6 alkoxycarbonyl, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl group, an 3- to 6-membered heterocyclic group substituted by or substituted with G ²¹ , cyano group, halogen group, C1~6 alkylene group, C1~6 alkylenedioxy group, pendant oxy group, C3-8 cycloalkyl group C1 ~ 6 alkyl, unsubstituted or substituted with G ²¹ C6 ~ 10 aryl group of a C1 ~ 6 alkyl, unsubstituted or substituted with the G ^21-membered heterocyclic group having 3 to 6 a C1 ~ 6 alkyl, C3 ~ 8 cycloalkoxy group having a C1 to 6 alkyl, unsubstituted or substituted with G ²¹ C6 ~ 10 aryloxy group of a C1 to 6 alkyl, unsubstituted or substituted with the 3 G ²¹ ~ ~ 6-membered heterocyclic group having a C1 6 alkyl, C1 ~ 6 alkylene group, C1 ~ 6 alkoxyimino group, unsubstituted or substituted with G ²¹ C6 ~ 10 aryl group of C1 ~ 6 alkoxyimino group, C1 ~ 6 alkoxy, or Base base.

C1~6 alkyl group, C3~8 cycloalkyl group, C1~6 halogenated alkyl group, C1~6 alkoxy C1~6 alkyl group, C1~6 alkoxy group, C1~6 alkoxy group C1 in G ⁴ ~6 alkoxy, C1-6 alkyloxycarbonyl, C1~6 alkylenedioxy, C6~10 aryl, C6~10 aryl C1-6 alkyl, 3-6 heterocyclyl, 3 a C1 ~ 6-membered heterocyclic group 1-6 alkyl group, a halogen group, a C1 to 6 alkylene, substituted group G ² and G ²¹ substituents as already described were based.

The C2-6 alkenyloxy group is substituted with a C2-6 alkenyl group on the hydroxyl group. Examples of the C2-6 alkenyloxy group include a vinyloxy group, a 1-propenyloxy group, and a 2-propenyloxy group (allyloxy group).

The C2-6 alkenyloxy C1-6 alkyl group is substituted with a C2-6 alkenyl group on the C1-6 alkyl group. Examples of the C2-6 alkenyloxy C1-6 alkyl group include a vinyloxymethyl group and an allyloxymethyl group.

Examples of the C3-8 cycloalkyl C1-6 alkyl group include a cyclopropylmethyl group and a cyclopentylmethyl group.

Examples of the C3-8 cycloalkyloxy C1-6 alkyl group include a cyclopropoxymethyl group and a cyclohexyloxymethyl group.

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

The 3-6 membered heterocyclic oxy C1-6 alkyl group is preferably a 5- to 6-membered heteroarylmethyl group such as a pyrazolylmethyl group or a pyridyloxymethyl group.

Examples of the C1-6 alkylene group include a methylidene group and a propane-2-ylidene group.

Examples of the C1-6 alkoxyimine group include a methoxyimino group (MeO-N=) and an ethoxyimino group (EtO-N=).

Examples of the C6-10 aryl C1-6 alkoxyimine group include a benzyloxyimino group (BnO-N=).

Examples of the C1-6 alkyl sulfonium group include a methyl fluorenyl group (MeNH-N=) and an ethyl fluorenyl group (EtNH-N=).

In the above, G ^{4 is} preferably a C1-6 alkyl group, a C1-6 halogenated alkyl group, a C1-6 alkoxy C1-6 alkyl group, a C2-6 alkenyl C1-6 alkyl group, a hydroxyl group, or the like. a C1 to 6 alkoxy group, a C1 to 6 alkoxycarbonyl, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl group (preferably phenyl), unsubstituted or substituted with the 3 G ²¹ - 6 Heterocyclic group (preferably pyridyl, pyrimidinyl, dioxolyl), halo, C1-6 alkyl, C1-6 alkyl dioxy, pendant oxy, unsubstituted or via G ²¹ unsubstituted C6 ~ 10 aryl group of C1 ~ 6 alkyl group (preferably a benzyl group), unsubstituted or substituted by the G21 3 ~ 6-membered heterocyclic group C1 ~ 6 alkyl group (preferably pyridinylmethyl , pyrazolylmethyl, triazolylmethyl), unsubstituted or substituted by G ²¹ C6-10 aryloxy C1-6 alkyl (preferably phenoxymethyl), unsubstituted or via G- ²¹ substituted 3-6 membered heterocyclooxy C1-6 alkyl (preferably pyrazolyloxymethyl), C1-6 alkylene, C1-6 alkyl alkoxy.

The substituent G ²¹ in G ⁴ is preferably a C1-6 halogenated alkyl group, a C1-6 halogenated alkoxy group, or a halogen group.

The B ^a B ^a carbon atom or a part of a substituted group G ⁴ of carbon atoms may also be bonded to Ar ² to form the upper 5 to 6-membered ring. Examples of the 5- to 6-membered ring include a cyclopentene ring, a cyclohexene ring, a dihydrofuran ring, a dihydrodioxin ring, a dihydropyran ring, and the like, and preferably a ring. Pentene ring, cyclohexene ring, dihydrodioxane ring, dihydropyran ring.

The pyridine compound of the present invention also contains a hydrate, various solvates or polymorphs. Further, the pyridine compound of the present invention contains a stereoisomer based on an asymmetric carbon atom, a double bond or the like, and a mixture or tautomer thereof.

[Tautomers]

In the case where R ⁴ is a hydrogen atom, the pyridine compound of the present invention produces a tautomeric pyridin-4-one compound as shown below. Further, R ¹ , R ² , R ³ and Q in the formulae have the same meanings as defined in the formula (I). In the present invention, the tautomeric pyridin-4-one compound is also included in the present invention.

[stereoisomer]

In the present invention, although the compounds represented by the same structural formula are used, the compounds having different spatial arrangements of atoms or substituents in the structure, such as optical isomers, non-image isomers, geometric isomers and the like are all three-dimensional. Isomers are also included in the present invention. Stereoisomers can be a single substance It can also be a mixture.

[salt]

The salt of the compound (I) of the present invention is not particularly limited as long as it is an agriculturally acceptable salt. Examples thereof include 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; and salts of transition metals such as iron and copper. A salt of an organic base such as ammonia, triethylamine, tributylamine, pyridine or hydrazine. The salt of the compound (I) can be obtained from the compound (I) by a known method.

[Agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides]

The agricultural and horticultural fungicide, the pest control agent, and the insecticidal or acaricidal agent of the present invention contain at least one selected from the group consisting of the compound (I) or a salt thereof (hereinafter sometimes referred to as "the compound of the present invention"). Active ingredient.

The agricultural and horticultural fungicide of the present invention can be used for controlling a wide range of filamentous fungi, for example, belonging to the genus Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and zygomycetes ( Plant diseases caused by the bacteria of Zygomycetes).

Examples of plant diseases and pathogenic bacteria to be controlled are shown below.

Beets: brown spot disease (Cercospora beticola), Aphanomyces cochlioides, root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), etc.

Peanut: brown spot disease (Mycosphaerella arachidis), spot disease (Ascochyta sp.), rust (Puccinia arachidis), blight (Pythium debaryanum) , rust spot (Alternaria alternata), white rickets (white Sclerotium rolfsii, black scorpion (Mycosphaerella berkeleyi), etc.

Cucumber: Powdery mildew (Sphaerotheca fuliginea), Phytophthora (Pseudoperonospora cubensis), Bacterial wilt (Mycosphaerella melonis), Stem rot (Fusarium oxysporum) )), sclerotinia sclerotiorum (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot disease (Cladosporium cucumerinum), brown spot Disease (Corynespora cassicola), Bacterial blight (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis sp., spotted bacteria Disease (Pseudomonas syringae pv. Lachrymans), etc.

Tomato: Botrytis cinerea (Botrytis cinerea), leaf mold (Cladosporium fulvum), Phytophthora infestans, and half-body wilt (Verticillium albo-atrum) )), powdery mildew (Oidium neolycopersici), ring disease (Alternaria solani), coal mold (Pseudocercospora fuligena), etc.

Eggplant: Botrytis cinerea, black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), coal mold (Mycovellosiella) Nattrassii)), Sclerotinia sclerotiorum, etc.

Strawberry: Botrytis cinerea, powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum) Fragariae), Phytophthora cactorum, soft rot (Rhizopus stolonifer), Fusarium oxysporum, etc.

Onions: gray spoilage (Botrytis allii), Botrytis cinerea, Botrytis squamosa, bacterium (Peronospora destructor), white blight (Phytophthora) Porri)

Cabbage: Rhizobium (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campestris pv. campestris), black spot bacterial disease (Pseudomonas syringae pv. maculicola, Pseudomonas syringae pv. alisalensis), Phytophthora (Peronospora parasitica), Sclerotinia sclerotiorum, Black coal disease (Alternaria brassicicola) , Botrytis cinerea, etc.

Green beans: Sclerotinia sclerotiorum, Botrytis cinerea, anthracnose (Colletotrichum lindemuthianum), horn spot disease (Phaeoisariopsis griseola), etc.

Apple: powdery mildew (Podosphaera leucotricha), black spot disease (Venturia inaequalis), candidiasis (Monilinia mali), black spot disease (Mycosphaerella pomi), Rot disease (Valsa mali), spotted leaf disease (Alternaria mali), brown spot disease (Gymnosporangium yamadae), Botryosphaeria berengeriana, anthracnose (apple) Anthrax (Glomerella cingulata), Colletotrichum acutatum, Diplocarpon mali, Zygophiala jamaicensis, Gloeodes pomigena, Helicoptera (Melocobisidium mompa), Botrytis cinerea, etc.

Plum: Black spot disease (Cladosporium carpophilum), Botrytis cinerea, brown rot (Monilinia mumecola), etc.

Persimmon: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), keratosis (Cercospora kaki), etc.

Peach: brown rot (Monilinia fructicola), Cladosporium carpophilum, Phomopsis sp., and perforated bacterial disease (Xanthomonas campestris pv. pruni) )Wait

Almond: brown rot (Monilinia laxa), spot disease (Stigmina carpophila), black spot disease (Cladosporium carpophilum), leaf defect disease (Polystigma rubrum), spotted leaf disease (Alternaria alternata), anthracnose (like gypsum Colletotrichum gloeosporioides, etc.

Cherry: brown rot (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), Monilinia kusanoi, etc.

Grapes: Botrytis cinerea, powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), Phytophthora (Plasmopara viticola) )), black pox (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot ( Coniella castaneicola)

Pear: Ventura nashicola, Gymnosporangium asiaticum, Black spot (Alternaria kikuchiana), Botryosphaeria berengeriana, Phyllactinia mali, blight (Phomopsis fukushii), brown spot disease (cystic sputum) Stemphylium vesicarium, anthracnose (Glomerella cingulata), etc.

Tea: round spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis), etc.

Citrus: Elsinoe fawcetti, Penicillium (Penicillium italicum), Green mold (Penicillium digitatum), Botrytis cinerea, Black spot (Citrus black spot) Disease (Diaporthe citri), ulcer disease (Xanthomonas campestris pv. Citri), powdery mildew (Oidium sp.), etc.

Wheat: Erysiphe graminis f.sp. Tritici, Scab (Gibberella zeae), Puccinia recondita, brown snow rot (Pythium iwayamai) )), red snow rot (Monographella nivalis), eye spot disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight blight (Leptosphaeria nodorum), snow rot fungus sclerotium (milk rot fungus brown granules) Typhula incarnata, Myriosclerotinia borealis, blight (Gaeumannomyces graminis), ergot (Claviceps purpurea), black stalk Disease (Tilletia caries), smut (Ustilago nuda), etc.

Barley: variegated disease (Pyrenophora graminea), reticular disease (Pyrenophora teres), moire (Rhynchosporium secalis), smut (Ustilago) Tritici, U.nuda), etc.

Rice: rice blast (Pyricularia oryzae), sheath blight (Rhizoctonia solani), long-term disease (Gibberella fujikuroi), flax leaf blight (rice leaf blight) Pathogen (Cochliobolus miyabeanus), Pythium graminicolum, Bacterial blight (Xanthomonas oryzae), Burkholderia plantarii, Acidovorax avenae, Bacterial Bacterial blight (Burkholderia glumae), strip blight (Cercospora oryzae), rice smut (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia, Alternaria padwickii, Epiccam purpurascenns, etc.

Tobacco: Sclerotinia sclerotiorum, Erysiphe cichoracearum, Phytophthora nicotianae, etc.

Tulip: Botrytis cinerea, etc.

Sunflower: Phytophthora (Plasmopara halstedii), Sclerotinia sclerotiorum, etc.

Kobresia: Sclerotinia borealis, large patch (Rhizoctonia solani), Sclerotinia homoeocarpa, Pyricularia sp., Erythrosia (Pythium) Pythium aphanidermatum)), anthracnose (Colletotrichum graminicola), etc.

Orchard grass: powdery mildew (Erysiphe graminis), etc.

Soybean: Purple spot disease (Cercospora kikuchii), Phytophthora (Peronospora manshurica), Stem blight (Phytophthora sojae), Rust (Phakopsora pachyrhizi) ), Sclerotinia sclerotiorum, Anthracnose (Colletotrichum truncatum), Botrytis cinerea, etc.

Potatoes: Phytophthora infestans, summer blight (Alternaria solani), Thanatephorus cucumeris, etc.

Banana: banana wilt disease (Fusarium oxysporum), banana leaf spot (Mycosphaerella fijiensis, Mycosphaerella musicola), etc.

Rapeseed: Sclerotinia sclerotiorum, root disease (Phoma lingam), black spot (Alternaria brassicae), etc.

Coffee: rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), brown eye (Cercospora coffeicola), etc.

Sugar cane: brown rust (Puccinia melanocephala), etc.

Corn: Leopard's disease (Gloecercospora sorghi), rust (Puccinia sorghi), southern rust (Puccinia polysora), smut (Ustilago maydis), Flax leaf blight (Cochliobolus heterostrophus), Setophaeria turcica, etc.

Cotton: seedling blight (Pythium sp), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii) ))Wait

The insecticidal or acaricidal agent of the present invention is excellent in the control effect against various pests such as agricultural pests and mites which affect plant growth. The insecticidal or acaricidal agent of the invention is not only sensitive Pests of susceptible strains are effective and are also effective against pests of strains that have developed resistance to previous agents, such as organophosphorus or carbamate agents. Representative examples of the pests of the resistant strain include the diamondback moth, the floating dust, the leafhopper, the aphid, and the like.

The pest control agent of the present invention exhibits an effect on the control of pests other than agricultural pests and mites. Examples of the harmful organism include external parasites, sanitary pests, and the like.

Examples of plants which can be used for the agricultural and horticultural fungicides, pest control agents, and insecticidal or acaricidal agents of the present invention include cereals, vegetables, root vegetables, potatoes, trees, pastures, and lawns. Classes, etc.

The agricultural and horticultural fungicides, pest control agents, and insecticidal or acaricides of the present invention can be applied to various parts of plants, for example, leaves, stems, stems, flowers, flower buds, fruits, seeds, buds, roots, Tubers, roots, seedlings, cuttings, etc. Further, it is also possible to use improved varieties, varieties, cultivars, further mutants, hybrids, and genetically modified bodies (GMOs) of such plants.

The agricultural and horticultural fungicide of the present invention can be used for seed treatment, stem and leaf spraying, soil application, surface application, and the like for controlling various diseases occurring in agricultural and horticultural crops including flowers, lawns, and pastures.

The agricultural and horticultural fungicide, the pest control agent, and the insecticide or acaricide agricultural and horticultural fungicide of the invention can also be combined with other agricultural and horticultural plants having the effects of sterilization, insecticide or acaricidal, nematicidal and soil-killing pests. Use of a medicament; a plant growth regulator, a synergist, a fertilizer, a soil conditioner, an animal feed, or the like, or a combination thereof.

An example of this is shown below.

Fungicides: (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: benalaxyl, dextrodamine, furalaxyl, metalaxyl, right Dales; oxadixyl; clozylacon, ofurace; (b) adenosine deaminase inhibitors: bupirimate, dimethirimol, dimethoate Ethirimol; (c) DNA/RNA synthesis inhibitors: hymexazole, octhiminone; (d) DNA topoisomerase II inhibitor: oxolinic acid (2) mitotic mitotic inhibitors and cell division inhibitors: (a) β-tubulin polymerization inhibitors: benomyl (benomyl), carbendazim, chlorfenazole, wheat ears Fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; diethofencarb; zoxamide; ethaboxam; (b) cell division inhibitor: pencycuron; (c) delocalization inhibitor of spectrin: fluopicolide; (3) respiratory inhibitor: (a) complex I NA DH oxidoreductase inhibitor: diflumetorim; tolfenpyrad; (b) complex II succinate dehydrogenase inhibitor: benodanil, flutolanil, extinction Mepronil; isofetamid; floopyram; fenfuram, furmecyclox; carboxin, oxycarboxin; thifluzamide; Benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, pyrithione Penthiopyrad, sedaxane; boscalid; (c) complex III panthenol oxidase Qo inhibitor: azoxystrobin, coumoxystrobin, Coamethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin, pyraclostrobin Pyrametostrobin), triclopyricarb; kresoxim-methyl, triflo Xystrobin); dimoxystrobin, fenaminstrobin, metominostrobin, oressastrobin; famoxadone; fluoxastrobin; imidazole Fenamidone; pyridencarb; (d) complex III panthenol reductase Qi inhibitor: cyazofamid; amisulbrom; (e) oxidative phosphorylation decoupling Binding agents: binapacryl, meptyldinocap, dinocap; fluazinam; ferimzone; (f) oxidative phosphorylation inhibitor (ATP synthase) Inhibitors): triphenylacetate, triphenylchlorotin, triphenylhydroxytin; (g) ATP production inhibitor: silthiofam; (h) complex III: cytochrome bcl (ubiquinone reductase) Qx (unknown) inhibitor: acetoctradin; (4) amino acid and protein synthesis inhibitors (a) methionine biosynthesis inhibitors: amine extinguish (andoprim), cypro ( Cyprodinil), mepanipyrim, pyrimethanil; (b) protein synthesis inhibitor: blasticidin-S; carbachol (kasuga) (mycin), cathamycin hydrochloride; streptomycin; oxytetracycline; (5) signal delivery inhibitors: (a) signal delivery inhibitors: quinoxyfen, propoxyquinol ( Proquinazid); (b) MAP/histidine kinase inhibitors in osmotic pressure signaling: fenpiclonil, fludioxonil; chlozolinate, iprodione, extinguish Procymidone, vinclozolin; (6) lipid and cell membrane synthesis inhibitors: (a) phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, propyl sheisson (iprobenfos) ), white pine (pyrazophos); rice scorpion (isoprothiolane); (b) lipid peroxidizer: biphenyl, chloroneb, chloramine (dicloran), pentachloronitrobenzene (quintozene), four Etnazene, tolclofos-methyl; etridiazole; (c) agents acting on the cell membrane: iodocarb, propamocarb, Propamocarb hydrochloride, propamocarb-fosetylate, prothiocarb; (d) disturbing the cell membrane of the pathogen Microorganisms: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain; (e) Agent for disturbing cell membrane: extract of tea tree; (7) Steroidal organism of cell membrane Synthetic inhibitors: (a) Demethylation inhibitors at position C14 in sterol biosynthesis: triforine; pyrifenox, pyridine Pyrosoxazole; fenarimol, flurprimidol, nuarimol; imazalil, sulphuric acid, Ixazole (oxoconazole), pefurazoate, prochloraz, triflumizole, viniconazole, azaconazole, bitertanol, bromide Bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, dextran, epoxiconazole, etaconazole , fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, cis-fluconazole, hexaconazole, easy amine Block (imibenconazole), ipconazole, metconazole, myclobutanil, penconazole, propiconazole, quinconazole, simeconazole , tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole; (b) sterol △14 reduction in biosynthesis And △ 8 → △ 7- isomerase inhibitors: Adi Aldimorph, Dodemorph, acetic acid Fungi, fenpropimorph, tridemorph; fenpropidin, piperalin; snail Spiroxamine; (c) 3-ketoreductase inhibitor in the C4 demethylation of sterol biosynthesis: fenhexamid; fenpyrazamine; (d Squalene epoxidase inhibitors: pyributicarb; naftifine, terbinafine; (8) inhibition of cell wall synthesis (a) Trehalase inhibitor: validamycin; (b) chitin synthase inhibitor: polyoxin (polyoxin), polyoxorim (polyoxorim); (c) Cellulase synthase inhibitor: dimethomorph, fluoride Flumorph, butyro Pyrimorph; benthiavalicarb, iprovalicarb, tolprocarb, valifenalate; mandipropamid; (9) melanin biosynthesis inhibitor (a) melanin biosynthesis reductase inhibitor : fthalide; pyroquilone; tricyclazole; (b) dehydratase inhibitor of melanin biosynthesis: carpropamid; diclocymet; Fenoxanil; (10) resistance inducing agent for host plants: (a) an agent acting on the salicylic acid synthesis pathway: acidified benzothiadiazole-S-methyl ester; (b) other: culling heat (probenazole); tiadinil; isotianil; laminarin; extract of giant knotweed; (11) unidentified agents: cymoxanil, fosetyl- Aluminium), phosphoric acid (phosphate), tecloftalam, imidazole (triazoxide), flusulfamide, diclomezine, methasulfocarb, cyflufenamid, metrafenone, pyrofenone, polydatin (dozine), doxorubicin, flutianil; (12) agents with multiple sites: copper (copper salt), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, oxygen chloride Copper, copper sulfate, sulfur, sulfur products, calcium polysulfide; ferbate, mancozeb, maneb, mancopper, metiram, Polyurethane, propineb, thiram, zineb, ziram; captan, captafol, sterilization Dan (folpet); chlorothalonil; dichlofluanid, tolylfluanid; guazatine, iminoctadine acetate, alkane sulfonate Net; anilazine; dithianon; chinomethionate; fluoroimide; (13) other agents: DBEDC, fluoride Fluorolpet, biguanide acetate, bis(8-hydroxyquinoline) copper (II), propamidine, chloropicrin, cyprofuram, agrobacterium, bethoxazine , diphenylamine, methyl isothiocyanate (MITC), mildiomycin, capsaicin, cufraneb, cyprosulfamide, dazome, debacarb ), dichlorophen, difenzoquat, wild swallow methanesulfonate, flumetover, calcium triethylphosphonate, sodium triethionate, irumamycin , natamycin, nitrothal-isopropyl, oxamocarb, propanosine sodium, pyrrolnitrin, tebufloquin, tolnifanide, cyanogen Azar (amide), Algophase, Amicarthiazol, Oxathiapiprolin, metiram-zinc, benthiazol, trichlamide, uniconazole, extinction Powderymycin, Oxyfenthiin, picarbutrazox; insecticidal/killing agents, nematicides, killing Pesticide: (1) Acetylcholinesterase inhibitor: (a) Amino acid ester system: alanycarb, aldicarb, bendiocarb, free gram ( Benfuracarb), butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, butyl Fenobucarb, formetanate, furathiocarb, isoprocarb, metiocarb, methodyl, oxamyl, bicap (pirimicarb), propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb; fensulfur (fenothiocarb), MIPC, MPMC, MTMC, aldoxycarb, allyxycarb, aminocarb, bufencarb, cloethocarb, metam- Sodium), (promecarb); (b) organophosphorus: acephate, azamethiphos, azinphos, methyl tamarind, Cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, methyl tausson, coumaphos, cyanophos, Demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, two Disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, blessing Fosthiazate, heptenophos, imicyafos, isofenphos, isocarbophos, isoxathio, malathion, degassos (mecarbam), methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl ), parathion, methyl balason, phenthoate, phorate, phosa Lone), phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prosulfadosone Prothiofos), pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terfufos, le Tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion; bromophos-ethyl, BRP, and fifeson ( Carbophenothion), cyanofenphos, CYAP, demeton-S-methylsulfone, dialifos, dichlofenthion, dioxabenzofos, etrimfos, Fensulfothion, flupyrazofos, fonofos, formothion, phosmethylan, isazofos, iodofenphos, extinction Methacrifos, pirimiphos-ethyl, phosphocarb, propylidene (pr Opaphos), prothoate, sulprofos; (2) GABA-functional chloride channel antagonists: chlordane, endosulfan, ethiprole ), fipronil, pyrafluprole, pyriprole; camphechlor, heptachlor; (3) sodium channel modulator: acrinathrin , ethnosine, allethrin, dextrorotatory, bifenthrin, bioallethrin, sulphate, S-cyclopentyl isomer, bioresmethrin, Cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, λ-saironin, γ-cylonine, cypermethrin ), alphacypermethrin, β-赛宁宁, θ-赛灭宁, ζ-赛灭宁, cyphenothrin ((1R)-trans isomer], dying (deltamethrin) ), empenhamin [(EZ)-(1R)-isomer], esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, care Match (flucythrinate), flumethrin, taufluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenol Phenothrin [(1R)-trans isomer], prallethrin, pyrethrum, resmethrin, silafluofen, sulphur Ester (tefluthrin), tetramethrin, chlorpyrifos [(1R)-isomer], tramomethrin, transfluthrin, allethrin, pyrethrin , Bielenin I, Bierin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, trans-hundengin Trans-permethrin), fenfluthrin, fenpirithrin, flubrocythrinate, flufenprox, metofluthrin, fenfluthrin (protrifenbute), pyrethyrrin (pyresmethrin), cyclopentethrin (terallethrin); (4) nicotinic acetylcholine receptor agonist: Off Pei (acetamiprid), clothianidin (clothianidin), Date Nan (dinotefuran), benefits of the amine (imidacloprid), nitenpyram (nitenpyram), nitro thiazol insect (nithiazine), thiacloprid, thiamethoxam, sulfoxaflor, nicotine; flupyradifurone; (5) nicotinic acetylcholine receptor ectopic modulator ( Allosteric modulator): spinetoram, spinosad; (6) chloride channel activator: abamectin, emamectin benzoate, lepimectin, Milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin , milbemycin oxime; (7) juvenile hormone analogues: hydroprene, kinoprene, metoprene, fenoxycarb, hundred Pyriproxyfen; diofenolan, epofenonane, triprene; (8) other non-specific inhibitors: methyl bromide, chloropicrin, sulfonate Sulfuryl fluoride, borax, tartar; (9) Selective homoptera antifeedant: flonicamid, pymetrozine ), new quinazoline (pyrifluquinazon); (10) terpene growth inhibitor: clofentezine (clofentezine), fluoroquinone (diflovidazin), hexythiazox, etoxazole; (11) microbial source insect midgut destruction agent: Bacillus thuringiensis subsp. Israelensis, Bacillus sphaericus ), Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Tenebrionis, Bt crop protein : Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1; (12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin , cyhexatin, fenbutatin oxide, propargite, tetradifon; (13) oxidative phosphorylation decoupling agent: chlorfenapyr, flubendiles Sulfaramid, DNOC; Baikeke, Dinobuton, Baijike; (14) Nicotinic acetylcholine receptor channel blocker: Bensultap, Pedan hydrochloride ( Cartap hydrochloride); Ereistoxin); thiosultap-monosodium, thiocyclam; (15) chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron , flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noififlumuron, teflubenzuron, three Triflumuron, buprofezin, fluzuron; (16) diptera molting agent: cyromazine; (17) ecdysone receptor agonist: cofen Chromafenozide, halofenozide, methoxyfenozide, tebufenozide; (18) octopamine receptor agonist: amitraz, demiditraz , chlordimeform; (19) mitochondrial electron transport system complex III inhibitor: acequinocyl, fluacrypyrim, hydramethylnon); (20) mitochondrial electron transport system complex I Inhibitors: fenazaquin, fenpyroximate, pyrimid Ifen), pyripaben, tebufenpyrad, defenfen, rotenone; (21) potential-dependent sodium channel blockers: indoxacarb, fluorinated Metaflumizone); (22) acetaminophen coenzyme A carboxylase inhibitor: spirodiclofen, spiromesifen, spirotetramat; (23) mitochondrial electron transport system complex IV inhibitor : Aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide; (24) mitochondrial electron transport system complex II inhibitor: cyenopyrafen (cyenopyrafen) (cyflumetofen), pyflubumide; (25) alkaloid receptor modulator: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole; (26) mixed Functional oxidase inhibitor compound: piperonyl butoxide; (27) latrophilin receptor drug: ester peptide (depsipeptide), cyclic ester peptide, 24 member cyclic ester peptide, Emodus ( Emodepside); (28) Other agents (unknown mechanism of action): azadirachtin (az Adirachtin), benzoximate, bifenazate, bromopropylate, chlorpyrifos, cryolite, dicofol, pyridalyl; benzene Chlorothiophene (benclothiaz), sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorobenzilate , clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimin, fluphenazine, gossyplure, chafer sex attractant (japonilure ), metoxadiazone, petroleum, potassium oleate, tetrasul, triarathene; afidopyropen, flometoquin, flufiprole, fluensulfone, chlorine Meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide; flulalaner, afoxolaner, fluxametamide 5-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroiso Zin-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49-3), broflanilide, and other meta-diamides.

[formulation formula]

The agricultural and horticultural fungicide, the pest control agent, and the insecticidal or acaricidal agent of the present invention are not particularly limited to the dosage form. For example, a dosage form such as a hydrating agent, an emulsion, an aqueous solvent, a particulate hydrating agent, a powder, or a tablet can be mentioned. The method of preparing the preparation is not particularly limited, and a known preparation method can be employed depending on the dosage form.

In the following, several formulation formulations are shown, but the additions and addition ratios are not limited to these examples and can vary widely. Parts in the formulation of the formulation represent parts by mass.

Several formulation examples are shown. Further, the formulation of the formulation shown below is merely illustrative, and modifications may be made without departing from the spirit of the invention.

(Formulation 1: Hydrating Agent)

40 parts of the compound of the invention

The above materials were uniformly mixed and pulverized into a fine form to obtain a hydrating agent having an active ingredient of 40%.

(Formulation 2: Emulsion)

The above materials were mixed and dissolved to obtain an emulsion having an active ingredient of 30%.

(Formulation 3: granules)

The above materials were uniformly mixed and pulverized into fine particles, and then granulated into granules having a diameter of 0.5 to 1.0 mm to obtain granules having an active ingredient of 5%.

(Formulation 4: granules)

The above materials were sufficiently pulverized and mixed, and water was added thereto and thoroughly kneaded, followed by granulation and drying to obtain granules having an active ingredient of 5%.

(Formulation 5: suspending agent)

The above materials were mixed and wet-pulverized until the particle size became 3 μm or less to obtain a suspending agent having 10% of the active ingredient.

[Examples]

Next, the embodiments are shown, and the present invention will be further described in detail. However, the present invention is not limited by the following examples.

(Example 1)

Manufacture of 1-(4-acetoxy-2,5,6-trimethylpyridin-3-yl)ethanone O-(4-trifluoromethylbenzyl)indole

(step 1)

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

Mixing 3.2 g of 4-amino-3-penten-2-one with 10.0 g of 2,2,5,6-tetramethyl-4H-1,3-dioxen-4-one, Stir at 120~130 ° C for 2.5 hours. Thereafter, the reaction liquid was cooled to room temperature, and diethyl ether was added to precipitate crystals. The crystal was separated by filtration to obtain a target compound. The yield was 38%.

The physical properties of the target compound are 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 T-butyl N-{(4-trifluoromethylbenzyl)oxy}carbamic acid

1.5 g of 4-trifluoromethylbenzyl bromide was dissolved in 20 ml of acetonitrile. 1.2 g of N-hydroxyaminocarbamic acid tert-butyl ester and 1.7 g of 1,8-diazabicyclo[5.4.0]-7-undecene were added to the solution, and the mixture was stirred at room temperature for 1 hour. Thereafter, the reaction solution was poured into 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride, then washed with a 10% aqueous sodium hydroxide solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound 2.28 g. The yield was 100%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.48 (9H, s), 4.91 (2H, s), 7.15 (1H, br. s), 7.51 (2H, d), 7.63 (2H, d)

(Step 3)

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

0.65 g of N-{(4-trifluoromethylbenzyl)oxy}aminocarboxylic acid tert-butyl ester was dissolved in 15 ml of 1,2-dichloroethane. To the solution, 0.30 g of 1-(4-hydroxy-2,5,6-trimethylpyridin-3-yl)-ethanone and 1 ml of trifluoroacetic acid were added, and the mixture was stirred at 50 to 60 ° C for 1 hour. Thereafter, the reaction solution was poured into a saturated aqueous solution of ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate 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 afford 0.20 g of the object compound. The yield was 34%.

The physical properties of the target compound are 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)indole

0.16 g of 1-(4-hydroxy-2,5,6-trimethylpyridin-3-yl)ethanone O-(4-trifluoromethylbenzyl)indole was dissolved in 10 ml of chloroform. To the solution were added 45 mg of pyridine and 43 mg of acetonitrile, and the mixture was stirred at room temperature overnight. Thereafter, the reaction liquid was diluted with chloroform, washed with 1N hydrochloric acid, and then washed with a saturated aqueous sodium hydrogen carbonate solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound (0.19 g). The yield was 100%.

The physical properties of the target compound are 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)

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

(step 1)

Synthesis of N-{2-(4-Trifluoromethylphenyl)ethoxy}phthalimidoimine

4-trifluoromethylphenylethanol 1.0g and N-hydroxyphthalimide 1.28 g was dissolved in 12 ml of tetrahydrofuran. To the solution was added 2.07 g of triphenylphosphine. To the solution was added dropwise 3.43 g of a 40% toluene solution of diethyl azodicarboxylate under ice cooling. The reaction solution was warmed to room temperature and stirred overnight. Thereafter, the solvent was distilled off under reduced pressure. The residue obtained was purified by a silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 4 / 1 (volume ratio)) to obtain 1.94 g of the object compound. The yield was 100%.

The physical properties of the target compound are 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 was dissolved in 20 ml of dichloromethane. The solution was cooled to 0 ° C, and 0.22 g of methylhydrazine was added dropwise. The reaction solution 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 give 0.83 g of desired compound. The yield was 94%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 2.96 (2H, t), 3.90 (2H, t), 5.43 (2H, br.s), 7.33 (2H, d), 7.55 (2H, d)

(Step 3)

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

0.83 g of O-{2-(4-trifluoromethylphenyl)ethyl}hydroxylamine was dissolved in 10 ml of 1,2-dichloroethane. To the solution were added 0.50 g of 1-(4-hydroxy-2,5,6-trimethylpyridin-3-yl)ethanone and 1 ml of trifluoroacetic acid, and stirred at room temperature overnight. Thereafter, the reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate, 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 give the title compound (0.68 g). The yield was 67%.

The physical properties of the target compound are as follows.

¹ H-NMR (DMSO-d ₆ , δ ppm) 1.79 (3H, s), 1.88 (3H, s), 2.11 (3H, s), 2.19 (3H, s), 3.00 (2H, t), 4.23 ( 2H, t), 7.49 (2H, d), 7.64 (2H, d), 10.96 (1H, br.s)

(Step 4)

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

Dissolving 1-(4-hydroxy-2,5,6-trimethylpyridin-3-yl)ethanone O-{2-(4-trifluoromethylphenyl)ethyl}anthracene 0.48g in dichloro Methane in 10ml. 0.19 g of triethylamine and 0.13 g of ethyl hydrazine chloride were added to the solution, and the mixture was stirred at room temperature overnight. Then, the reaction liquid was concentrated under reduced pressure, and the residue obtained was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to afford the title compound 0.38 g. The yield was 72%.

The physical properties of the target compound are 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)

Manufacture of 1-(4-acetoxy-2,5,6-trimethylpyridin-3-yl)ethanone O-(4-trifluoromethylphenyl)anthracene

(step 1)

Synthesis of T-butyl N-(4-trifluoromethylphenoxy)carbamate

2.0 g of 4-fluorobenzotrifluoride was dissolved in 24 ml of dimethyl hydrazine. To the solution was added 1.95 g of N-hydroxyaminocarbamic acid tert-butyl ester and 1.05 g of potassium hydroxide, and the mixture was stirred at room temperature overnight. Thereafter, the reaction liquid was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 4 / 1 (volume ratio)) to obtain 1.5 g of the target compound. The yield was 44%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.50 (9H, s), 7.19 (2H, d), 7.50 (1H, s), 7.56 (2H, d)

(Step 2)

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

0.85 g of N-(4-trifluoromethylphenoxy)carbamic acid tert-butyl ester was dissolved in 10 ml of 1,2-dichloroethane. To the solution, 0.50 g of 1-(4-hydroxy-2,5,6-trimethylpyridin-3-yl)-ethanone and 1 ml of trifluoroacetic acid were added, and the mixture was stirred at 50 ° C for 1 hour. Thereafter, the reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate, and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was washed with diethyl ether to give the title compound (0.39 g). The yield was 41%.

The physical properties of the target compound are 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)anthracene

1-(4-Hydroxy-2,5,6-trimethylpyridin-3-yl)ethanone O-(4-trifluoromethylphenyl)phosphonium 0.25 g was dissolved in 8 ml of dichloromethane. 0.10 g of triethylamine and 70 mg of ethyl hydrazine chloride were added to the solution, and the mixture was stirred at room temperature overnight. Then, the reaction liquid was concentrated under reduced pressure, and the residue obtained was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain the target compound (0.14 g). The yield was 49%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 2.10 (3H, s), 2.23 (3H, s), 2.32 (3H, s), 2.50 (3H, s), 2.55 (3H, s), 7.27 (2H, d), 7.57 (2H, d)

(Example 4)

Manufacture of 1-(4-acetoxy-2,5,6-trimethylpyridin-3-yl)carboxaldehyde O-{2-(4-trifluoromethylphenyl)ethyl}anthracene

(step 1)

Synthesis of ethyl 4-hydroxy-2,5,6-trimethylnicotinate

45 g of ethyl 3-aminobutenoate and ethyl 2-methylacetate 50 g Dissolved in 100 ml of xylene. The solution was heated to reflux for one night. Thereafter, it was cooled to room temperature. The precipitated crystals were filtered, washed with diethyl ether, and finally dried to give the title compound. The yield was 33%.

The physical properties of the target compound are 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 was dissolved in 120 ml of acetone. 21.0 g of cesium carbonate was added to the solution, followed by the addition of 10.0 g of methyl iodide, and the mixture was heated under reflux for 8 hours. Thereafter, the reaction liquid was cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound 10.0 g. The yield was 77%.

The physical properties of the target compound are 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. To the liquid, 10.0 g of ethyl 4-methoxy-2,5,6-trimethylnicotinate was added dropwise under ice cooling. After the completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours. Thereafter, the reaction liquid was cooled in an ice bath, water was added until the unreacted lithium aluminum hydride was decomposed, and finally dried by anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound 7.9 g. The yield was 97%.

The physical properties of the target compound are 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 was dissolved in 90 ml of benzene. To the solution, 15.2 g of manganese dioxide was added and heated to reflux for one night. Thereafter, the reaction liquid was cooled to room temperature, and filtered through celite. The filtrate was concentrated under reduced pressure to give the title compound 5. The yield was 77%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 2.22 (3H, s), 2.53 (3H, s), 2.73 (3H, s), 3.87 (3H, s), 10.50 (1H, 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 the solution, 33 ml of a 1 N boron tribromide/dichloromethane solution was added dropwise under ice cooling. After the completion of the dropwise addition, the mixture was stirred at room temperature for one night. Thereafter, the reaction solution was cooled in an ice bath, and neutralized by adding a 10% aqueous sodium hydrogencarbonate solution. The precipitated crystals were filtered, and finally dried to obtain 0.9 g of the objective compound. The yield was 33%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 2.18 (3H, s), 2.43 (3H, s), 2.53 (3H, s), 10.46 (1H, s)

(Step 6)

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

0.32 g of O-{2-(4-trifluoromethylphenyl)ethyl}hydroxylamine was dissolved in 10 ml of 1,2-dichloroethane. To the solution was added 0.26 g of 4-hydroxy-2,5,6-trimethylpyridine-3-carbaldehyde and a few drops of trifluoroacetic acid, and stirred at room temperature overnight. Thereafter, the reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate, 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 give the title compound 0.42 g. The yield was 76%.

The physical properties of the target compound are 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 (1H, s)

(Step 7)

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

0.42 g of 4-hydroxy-2,5,6-trimethylpyridine-3-carbaldehyde O-{2-(4-trifluoromethylphenyl)ethyl}anthracene was dissolved in 20 ml of dichloromethane. 0.22 g of triethylamine was added to the solution. Then, 0.14 g of ethyl hydrazine chloride was added under ice cooling, and the mixture was stirred at room temperature overnight. Thereafter, the reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate, and extracted with chloroform. The organic layer was then dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure, and the column is laminated with a rubber tube. The residue obtained by the purification method (developing solvent: n-hexane / ethyl acetate) was purified to give the title compound 0.37 g. The yield was 79%.

The physical properties of the target compound are 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 (1H, s)

(Example 5)

Manufacture of methyl [2,3,6-trimethyl-5-[[4-(4-trifluoromethoxy)phenyl]cyclohexyloxy]-4-pyridyl]carbonate

(step 1)

Synthesis of methyl 4-hydroxy-2-ethyl-5,6-dimethylnicotinate

13.6 g of methyl 3-amino-2-pentenoate and 20.0 g of 2,2,5,6-tetramethyl-4H-1,3-dioxan-4-one were mixed. Stir at 150 ° C for 5 hours. After cooling to room temperature, the precipitated crystals were filtered, washed with diethyl ether and dried to give the title compound (13.7 g). The yield was 31%.

The physical properties of the target compound are 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-dimethylnicotinate

13.7 g of methyl 4-hydroxy-2-ethyl-5,6-dimethylnicotinate was dissolved in 150 ml of acetonitrile. 18.2 g of potassium carbonate was added to the reaction liquid, followed by the addition of 15.8 g of allyl bromide, followed by heating under 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 dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound 16.6 g. The yield was 100%.

The physical properties of the target compound are 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 (1H, 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 the reaction mixture, 16.6 g of methyl 4-allyloxy-2-ethyl-5,6-dimethylnicotinate was added dropwise under ice cooling, and after stirring, stirring at room temperature 2 hour. Thereafter, the reaction solution was cooled in an ice bath, and water was added straight. The unreacted lithium hydride was decomposed and dried by anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the title compound 11.3 g. The yield was 77%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.26 (3H, t), 2.16 (3H, s), 2.46 (3H, s), 2.84 (2H, q), 4.39 (2H, d), 4.70 (2H, d), 5.29-5.45 (2H, m), 6.03-6.14 (1H, m)

(Step 4)

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

11.3 g of (4-allyloxy-2-ethyl-5,6-dimethylpyridin-3-yl)-methanol was dissolved in 120 ml of dichloromethane, and a saturated aqueous solution of sodium hydrogencarbonate was added under ice cooling. 120 ml, 0.6 g of potassium bromide and 4-sided oxy-TEMPO 0.4 g. Under cooling with an ice bath, 91 g of a 5% sodium hypochlorite solution was added dropwise to the reaction solution over 30 minutes. After completion of the dropwise addition, the mixture was stirred at 0 ° C for 30 minutes, and the reaction liquid was poured into ice water. The organic layer was dried over anhydrous magnesium sulfate by extraction with methylene chloride aqueous solution and saturated brine. 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 afford 11.1 g of the desired compound. The yield was 99%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.25 (3H, t), 2.21 (3H, s), 2.52 (3H, s), 3.06 (2H, q), 4.42 (2H, d), 5.32-5.43 ( 2H, m), 6.01-6.11 (1H, m), 10.47 (1H, s)

(Step 5)

1-(4-allyloxy-2-ethyl-5,6-dimethyl-3-pyridyl)-N-[2-[[3-chloro-5-(trifluoromethyl)-2 Synthesis of pyridyl]oxy]-1-methyl-propoxy]methylimine

0.5 g of 4-allyloxy-2-ethyl-5,6-dimethylpyridine-3-carbaldehyde was dissolved in 10 ml of dichloromethane. O-[2-[[3-chloro-5-(trifluoromethyl)-2-pyridyl]oxy]-1-methyl-propyl]hydroxylamine 0.8 was added to the reaction mixture under ice cooling. g, a few drops of trifluoroacetic acid, and stirred at room temperature for one night. The reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to yield 0.75 g of the desired compound. The yield was 68%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.19-1.43 (9H, m), 2.21 (3H, s), 2.52 (3H, s), 3.06 (2H, q), 4.33-4.42 (3H, m), 5.32-5.43(2H,m), 5.57-5.61(1H,m), 6.01-6.11(1H,m),7.79-8.25(3H,m)

(Step 6)

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

1-(4-Allyloxy-2-ethyl-5,6-dimethyl-3-pyridyl)-N-[2-[[3-chloro-5-(trifluoromethyl)- 0.5 g of 2-pyridyl]oxy]-1-methyl-propoxy]methylimine was dissolved in 10 ml of methanol. To the solution, 0.012 g of tetrakis(triphenylphosphine)palladium and 0.28 g of potassium carbonate were added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into ice water, extracted with chloroform, and 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 give the object compound (0.4 g). The yield was 87%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.17-1.41 (9H, m), 1.99 (3H, s), 2.22 (3H, s), 2.85 (2H, q), 4.33-4.42 (1H, m), 5.57-5.61 (1H, m), 7.78-8.22 (3H, m)

(Step 7)

[3-[2-[[3-chloro-5-(trifluoromethyl)-2-pyridyl]oxy-1-methyl-propoxy]iminomethyl]-2-ethyl- Synthesis of 5,6-Dimethyl-4-pyridyl]acetate

3-[2-[[3-chloro-5-(trifluoromethyl)-2-pyridyloxy]-1-methyl-propoxy]iminomethyl]-2-ethyl-5 0.4 g of 6-dimethyl-pyridin-4-ol was dissolved in 10 ml of chloroform. After 0.2 g of triethylamine was added to the solution, 0.16 g of ethyl hydrazine chloride was added thereto under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was poured into a saturated aqueous solution of sodium hydrogencarbonate and extracted with chloroform, 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 afford the title compound 0.37 g. The yield was 84%.

The physical properties of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.19-1.43 (9H, m), 2.06 (3H, s), 2.30 (3H, s), 2.51 (3H, s), 2.86 (2H, q), 4.43 4.45(1H,m), 5.59-5.62(1H,m),7.82-8.26(3H,m)

The compounds produced by the same methods as the above examples are shown in Tables 1 to 10.

And the physical property data of the compound is recorded in the column of "physical properties". The physical property data describes the melting point (° C.), the refractive index (n _D ), or the properties thereof.

The "E" shown in the column of "Three-dimensional Configuration" indicates that the double bond of the imine in the compound is the E configuration, "Z" is the Z configuration, and "EZ" indicates that the compound is the compound of the two configurations. mixture.

The table Ph means phenyl, Me means methyl, Et represents an ethyl group, ⁿ Pr represents n-propyl group, ⁱ Pr denotes an isopropyl group, ^c Pr a cyclopropyl group, ⁿ Bu represents a n-butyl group, ^t Bu represents a group The third butyl group, Py represents a pyridyl group, Ac represents an ethyl fluorenyl group, Bn represents a benzyl group, and PMB represents a p-methoxybenzyl group.

The first table discloses a compound in which the compound represented by the formula (I) is an organic group represented by the formula (I) (a compound represented by the formula (I-1) shown below).

In the compound represented by the formula (I), a compound represented by the formula (I) wherein Q is an organic group represented by the formula (II) (a compound represented by the formula (I-2) shown below) is disclosed. Here, the compounds described in the second to sixth tables are compounds in which R ¹ , R ² and R ³ are a methyl group.

The carbon atom to which * is attached to the structural formula in "B ^a " represents a carbon atom bonded to the oxygen of hydrazine (the same meaning is also expressed in the following table). Further, the carbon atom or nitrogen atom attached to ** in the structural formula in "B ^a " represents a carbon atom or a nitrogen atom bonded to "Ar ² " (the same meaning is also expressed in the following table).

Further, the compound c-187 in the third table is an N-oxide.

The seventh to eighth tables represent the substituents in the compound represented by the formula (I-3).

The ninth table represents a substituent in the compound represented by the formula (I-4).

The ¹ H-NMR data of some of the compounds described in the above Tables 1 to 10 are shown in Table 11.

[biological test]

The compound of the present invention is useful as an active ingredient of agricultural and horticultural fungicides by the following test examples.

(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 having an active ingredient of 5%.

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. Then, the chemical solution was sprayed on the wheat seedlings (variety "Chihoku", 1.0 to 1.2 leaf stage) cultivated in the vegetarian pot. Let the leaves dry. Thereafter, the conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) were inoculated and shaken in a greenhouse at 22 to 25 ° C for 7 days (treatment). On the other hand, the wheat seedlings were inoculated with the conidia of wheat powdery mildew without spraying the liquid, and kept in a greenhouse at 22 to 25 ° C for 7 days (no treatment). The state of the lesion on the leaf was compared with the untreated area and investigated, and the control value was calculated.

Control value (%) = 100 - {area of lesions (treatment) / area of lesions (no treatment)} × 100

The wheat powdery mildew control test was carried out on the compound shown in Table 12. The control value of any compound is 75% or more.

(Test Example 2) Wheat Red Rust Control Test-1

An emulsion was prepared by the same method as 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. Spray the liquid on the wheat seedlings cultivated in the simmered pots (variety "Nonglin No. 61", 1.0~1.2 leaf stage). Let the leaves dry. Thereafter, the summer spores of Puccinia recondita were inoculated with powder and kept in a greenhouse at 22 to 25 ° C for 10 days. The state of the lesion on the leaf was compared with the untreated condition in the same manner as in Test Example 1 and investigated, and the control value was calculated.

The wheat red rust prevention test was carried out on the compound shown in Table 13. The control value of any compound is 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 solution was diluted with water so that the active ingredient became 125 ppm to obtain a chemical solution. The above-mentioned liquid medicine was sprayed on the wheat seedlings (variety "Chihoku", 1.0 to 1.2 leaf stage) cultivated in the vegetarian pot. After the leaves were dried, the conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) were inoculated and kept in a greenhouse at 20-25 ° C for 7 days. The state of the lesion on the leaf was compared with the untreated condition in the same manner as in Test Example 1 and investigated, and the control value was calculated.

The disease control test was performed on the compound shown in Table 14. Any compound showed a control value of 75% or more.

(Test Example 4) Wheat Red Rust Control Test-2

An emulsion was prepared by the same method as Test Example 3. The emulsion was obtained by diluting the emulsion with water so that the active ingredient became 125 ppm. The above-mentioned liquid medicine is sprayed on the wheat seedlings cultivated in the simmered pots (variety "Nonglin No. 61", 1.0-1.2 leaf stage). After the leaves were air-dried, the summer spores of Puccinia recondita were inoculated and kept in a greenhouse at 20-25 ° C for 10 days. The state of the lesion on the leaf was compared with the untreated condition in the same manner as in Test Example 1 and investigated, and the control value was calculated.

The wheat red rust prevention test described above was carried out for the person shown in Table 15. Any compound showed a control value of 75% or more.

Then, it is useful to exhibit the compound of the present invention as an active ingredient of an insecticide or an acaricide by the following test examples.

(Test Example 5) Validation test for the effectiveness of the tantrum

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 were mixed and dissolved to prepare an emulsion having an active ingredient of 5%.

An agent having a compound concentration of 125 ppm was obtained by diluting the above emulsion with water. Cabbage leaves were immersed in the drug solution for 30 seconds and then air dried. Thereafter, the cabbage leaves are placed in a filter paper. In the culture dish, 2 second instar larvae of the genus Spodoptera were inoculated. The glass cover was placed and placed in a constant temperature and humidity chamber at a temperature of 25 ° C and a humidity of 65%. After 5 days, the life and death of the tick moth was observed, and the insecticidal rate was calculated. The test was repeated twice.

The compound shown in Table 16 was subjected to an efficacy confirmation test for Spodoptera litura. The insecticidal rate of either compound was 100%.

(Test Example 6) Validation test for the effectiveness of cotton aphid

The emulsion prepared in the same manner as in Test Example 5 was diluted with water to obtain a drug solution having a compound concentration of 125 ppm.

The cotton aphid was inoculated on the first leaf of a cucumber that was sown in a 3-inch pot and germinated for 10 days. After one day, the adult was removed, and the above-mentioned liquid medicine was sprayed on the cucumber parasitized by the laid nymph. The mixture was placed in a constant temperature and humidity chamber at a temperature of 25 ° C and a humidity of 65%. After 5 days, the life and death of the cotton aphid were observed, and the insecticidal rate was calculated. The test was repeated twice.

The compound shown in Table 17 was tested for efficacy against cotton aphid. The insecticidal rate of either compound was 100%.

(Test Example 7) Validation test for the efficacy of the two-point leafhopper

The emulsion prepared in the same manner as in Test Example 5 was diluted with water to obtain a drug solution having a compound concentration of 125 ppm. Ten adult mites were inoculated on the first leaves of the green beans germinated in a 3-inch sputum and germinated for 10 days. The above liquid was sprayed after 1 day. The temperature was set at 25 ° C and the humidity was 65% in a constant temperature and humidity chamber. After 3 days, the life and death of the two leaf mites were observed, and the insecticidal rate was calculated. The test was repeated twice.

The compound shown in Table 18 was tested for potency against the two-spotted spider mites. The insecticidal rate of either compound was 100%.

(Test Example 8) Validation test for the effectiveness of soybean meal

The emulsion prepared in the same manner as in Test Example 5 was diluted with water to obtain a drug solution having a compound concentration of 125 ppm. The cowpea is cultivated in a 3-inch sputum, and the soybean nymph is inoculated on the primary leaf. The above liquid is sprayed on the cowpea parasitized by the soybean meal nymph. The cowpea was placed in a constant temperature room at a temperature of 25 ° C and a humidity of 60%, and the life and death of the soybean meal was observed after 4 days. The test was repeated twice.

The compound shown in Table 19 was tested for potency against soybean meal. The insecticidal rate of any compound is 80% or more.

(Test Example 9) Confirmation test for the efficacy of Aesop's leafhopper

The emulsion prepared by the same method as Test Example 5 was diluted with water to obtain a compound concentration of 125. Ppm solution. The green beans were cultivated in a 3-inch sputum, and 10 female larvae were inoculated on the primary leaves. The above liquid medicine is sprayed on the green bean seedlings. The green beans were placed in a constant temperature room at a temperature of 25 ° C and a humidity of 65%, and the adult life was observed 10 days after the spraying.

The compound shown in Table 20 was tested for efficacy against the genus Astragalus. The insecticidal rate of any compound is above 90%.

[Industrial availability]

The pyridine compound of the present invention is a novel compound which has the effects of pest control, sterilization, acaricidal killing, insecticidal action, and the like, does not cause phytotoxicity to plants, and has little toxicity to human or animal fish or has little influence on the environment. In particular, it exhibits excellent control effects against wheat diseases. The pyridine compound of the present invention is useful as an active ingredient for 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)

a compound or a salt thereof, which is represented by formula (I), [In the formula (I), R ¹ represents a hydrogen atom, unsubstituted or ^{substituted. 1} G of C1 ~ 6 alkyl, unsubstituted or ^{substituted. 1} G of C1 ~ 6 alkoxy, unsubstituted or G ² substituted C6~10 aryl, unsubstituted or G ² substituted 3-6 membered heterocyclic group, cyano group or halogen group; R ² and R ³ each independently represent a hydrogen atom, unsubstituted or via G ^a substituted C1~6 alkyl group, an unsubstituted or G ¹ substituted C 3-8 cycloalkyl group, an unsubstituted or G ¹ substituted C 1-6 alkoxy group, a decyl group, a methyl methoxy group, Unsubstituted or G ¹ -substituted C 1-6 alkylcarbonyl, unsubstituted or G ¹ substituted C 1-6 alkylcarbonyloxy, unsubstituted or G ² substituted C 6 ～ 10 aryl, a C1~6 alkoxyimino)-C1~6 alkyl group, a cyano group or a halogen group which is unsubstituted or substituted with G ¹ ; here, R ¹ and R ² may also be combined with R ¹ and R ² The carbon atoms bonded to each of them form a 5-6 membered ring; R ⁴ represents a hydrogen atom, an unsubstituted or G ¹ substituted C ¹ ~ 6 alkyl group, an unsubstituted or G ¹ substituted C 2 6 olefin group, unsubstituted or substituted with G ¹ group of C2 ~ 6 alkynyl, unsubstituted or substituted with G ¹ of C3 ~ 8 cycloalkyl, unsubstituted or substituted with the C6 ~ 1 G ² 0 aryl C1~6 alkyl, unsubstituted or G ² substituted 3-6 membered heterocyclic group, unsubstituted or G ² substituted 3-6 membered heterocyclic C1-6 alkyl group, formazan group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl carbonyl, unsubstituted or substituted with G ¹ of C3 ~ 8 cycloalkylcarbonyl, unsubstituted or substituted with G ¹ group of C1 ~ 6 alkenyl carbonyl group Unsubstituted or G ² substituted C 6-10 arylcarbonyl, unsubstituted or G ¹ substituted C 1-6 alkoxycarbonyl, unsubstituted or G ¹ substituted C 2 -6 oxycarbonyl , unsubstituted or substituted with G ¹ of C1 ~ 6 alkylsulfonyl group, unsubstituted or G ¹ of C1 ~ 6 alkyl substituted aminocarbonyl, unsubstituted or substituted with G ¹ of (C1 ~ 6 alkylthio) carbonyl, unsubstituted or substituted with G ¹ group of C1 ~ 6 alkyl (thiocarbonyl), or formula (IV) represented by the group; In the formula (IV), G ^a each independently represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ - 6 alkyl group, an unsubstituted or G ¹ -substituted C 2 - 6 alkenyl group, unsubstituted or via G ¹ substituents of C2 ~ 6 alkynyl, unsubstituted or substituted with G ¹ of C3 ~ 8 cycloalkyl, or unsubstituted or substituted G ² of the C6 ~ 10 aryl group; in the formula (IV), G ^b It represents a hydrogen atom, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl, unsubstituted or substituted with G ¹ of C2 ~ 6 alkenyl, unsubstituted or substituted with G ¹ of C2 ~ 6 alkynyl group, an substituted or substituted by G ¹ of C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ² of the C6 ~ 10 aryl group, or an unsubstituted or substituted G ² of the 3 to 6-membered heterocyclic group; the formula ( In IV), T represents an oxygen atom, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio)carbonyl group, a carbonyl group (thio group), a (thio)carbonyloxy group, or an oxycarbonyl group ( a divalent group represented by thio) or -OC(=O)-N(G ^b )-; * represents a bonding position of a group represented by the formula (IV); and Q represents a formula (II) or a formula (III) Any of the organic bases indicated; [In the formulae (II) and (III), Ar ¹ represents an unsubstituted or G ² -substituted C 6-10 aryl group, or an unsubstituted or G ² -substituted 3-10 membered heterocyclic group; Ar ^{2 ;} An unsubstituted or G ² -substituted C6-10 aryl group, an unsubstituted or G ² -substituted C6-10 aryloxy group, an unsubstituted or G ² -substituted C6-10 arylthio group, Substituted or G ² substituted C6-10 sulfinyl, unsubstituted or G ² substituted C6-10 sulfonyl, unsubstituted or G ² substituted 3-10 heterocycle group, unsubstituted or substituted by G ² of the 3 to 10-membered heterocyclic group, unsubstituted or substituted with G ² of the 3 to 10-membered heterocyclic group or a ferrocenyl group; R ^a represents a hydrogen atom, an Substituted or substituted by C ¹ C1~6 alkyl, unsubstituted or substituted by G ¹ C3-8 cycloalkyl, amine, C1-6 alkylcarbonylamino, or unsubstituted or via G ² Substituted C6~10 aryl; B ^a represents unsubstituted or G ⁴ substituted C1~C6 alkylene group, unsubstituted or substituted by G ⁴ C2~C6 alkenylene group , unsubstituted or substituted with G ⁴ of C2 ~ C6 alkynyl group extension (alkynylene group), unsubstituted or substituted with G ⁴ of C1 ~ C6 alkoxy extending C1 ~ 6 alkylene, unsubstituted or substituted with G ⁴ of C3 ~ C6 cycloalkyl extension (cycloalkylene group), G ⁴ unsubstituted or substituted alkylene group of C1 ~ C6 cycloalkyl, C3 ~ 6 extends Unsubstituted or substituted by C ⁴ C1~C6 alkoxy C3~6 cycloalkyl, unsubstituted or G ⁴ substituted C4~C6 cycloalkenylene group, or unsubstituted Or a 3 to 6 member heterocyclicylene group substituted by G ⁴ ; further, ^a carbon atom of B ^a or ^{a part} of the substituent G ⁴ on B ^a may also be bonded to a carbon atom on Ar ² to form 5~6 member ring; * indicates 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 methyloxy group, a C1-6 alkyloxycarbonyl group, a C1-6 alkoxycarbonyloxy group, a cyano group, or a halogen group; and R ¹ , R ² , R ³ When two or more of R ⁴ or R ^a are the above-mentioned groups substituted by G ¹ , the G ¹ may be the same or different from each other; G ² represents a C1-6 alkyl group, a hydroxy C1-6 alkyl group, C2~6 alkenyl group, C2~6 alkynyl group, C3~8 cycloalkyl group, C1~6 halogenated alkyl group, C1~6 alkoxy C1~6 alkyl group, C1~6 alkoxy C1~6 halogen Alkyl, C2-6 halogenated alkenyl, C2-6 halogenated alkynyl, hydroxy, C1-6 alkoxy, C3~8 cycloalkyl C1~6 alkoxy, C1~6 alkoxy C1~6 alkoxy Base, C1~6 halogenated alkoxy group, C1~6 halogenated alkoxy C1~6 halogenated alkoxy group, formyl group, C1~6 alkylcarbonyl group, C1~6 alkoxycarbonyl group, formyloxy group, C1 1-6 alkylcarbonyloxy group, a C1 - 6 alkoxycarbonyl group, a C1 - 6 alkoxycarbonyl group, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl group, unsubstituted or G ²¹ the C6 ~ 10 aryl substituted with a C1 to 6 alkyl group, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryloxy, unsubstituted or substituted with the G ²¹ 3 to 6-membered heterocyclic group, unsubstituted or 3-6 membered heterocyclic oxy group substituted by G ²¹ , C1~6 alkylthio group, C1-6 alkyl sulfinyl group, C1~6 alkylsulfonyl group, C1~6 halogenated alkylthio group, C1~ 6 alkylsulfinyl acyl halides, C1 ~ 6 halogenated alkylsulfonyl group, a pentafluoroethyl group (pentafluorosulfanyl group), unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl group, unsubstituted or G ²¹ substituted aryl of C6 ~ 10 alkylsulfinyl acyl, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl sulfonic acyl group, a nitro group, a cyano group, a halogen group, C1 ~ 6 alkylene, C1 ~ 6 Alkyl dioxy Or a halogenated C1 ~ 6 alkylene dioxy; to ^{R 1, R 2, R 3} , R 4, R a, G 4, two or more Ar ¹ or Ar ² in the G ² is substituted by the above group of In this case, the G ² may be the same or different from each other; G ²¹ represents a C1-6 alkyl group, a C1-6 halogenated alkyl group, a C1-6 alkoxy group, a C1-6 alkoxylated alkoxy group, or a halogen group; When ^two or more of G ² or G ⁴ is a group substituted with G ²¹ , the G ²¹ may be the same or different from each other; G ⁴ represents a C1-6 alkyl group, a C3-8 cycloalkyl group, and C1. ~6 halogenated alkyl, C1~6 alkoxy C1~6 alkyl, C2~6 alkenyl C1~6 alkyl, hydroxy, C1-6 alkoxy, C1~6 alkoxy C1~6 alkoxy group, C2 to 6 alkenyl group, a C1 to 6 alkoxycarbonyl, unsubstituted or substituted with the G ²¹ C6 ~ 10 aryl group, unsubstituted or substituted with of ²¹³ G to 6-membered heterocyclic group, a cyano a group, a halogen group, a C1~6 alkylene group, a C1~6 alkylenedioxy group, a pendant oxy group, a C3-8 cycloalkyl C1-6 alkyl group, an unsubstituted or ^C21 substituted ^C21 ~10 Aryl C1~6 alkyl, unsubstituted or G ²¹ substituted 3-6 membered heterocyclic C1-6 alkyl, C3-8 cycloalkoxy C1-6 alkyl, unsubstituted or via G ²¹ Substituted C6~10 aryloxy C1~6 alkyl, not Unsubstituted or substituted by G of ²¹ 3 to 6-membered heterocyclic group having a C1 to 6 alkyl group, a C1 1-6 alkylene (alkylidene group), C1 ~ 6 alkoxyimino group, an unsubstituted or substituted by G ²¹ The C6~10 aryl C1~6 alkoxyimino group or the C1~6 alkyl fluorenyl group]. An agricultural and horticultural fungicide comprising at least one selected from the group consisting of a compound of the first aspect of the patent application and a salt thereof as an active ingredient. A pest control agent containing at least one selected from the group consisting of a compound of the first aspect of the patent application and a salt thereof as an active ingredient. An insecticidal or acaricidal agent containing at least one selected from the group consisting of the compound of the first aspect of the patent application and a salt thereof as an active ingredient.