TW201908303A - Pyridine compound and its use - Google Patents

Abstract

The present invention provides a pyridine compound represented by formula (I) (wherein R1 to R4 each represent a hydrogen atom, an unsubstituted or G1-subsutituted C1-6 alkyl group or the like, A represents an oxygen atom or the like, Cy represents a C6-10 aryl group or the like), an N-oxide compound thereof, or a tautomer or salt thereof. The present invention also provides a fungicide for agricultural and horticultural use, a harmful organism control agent, and insecticide or acaricide including at least one selected from the group consisting of a compound represented by formula (I), and a tautomer and salt thereof as an active ingredient.

Description

   Pyridine compounds and uses thereof   

The present invention relates to the use of a pyridine compound, fungicides for agricultural and horticultural purposes, pest control agents, and insecticides or acaricides.

In the cultivation of agricultural and horticultural crops, a large number of pesticides have been proposed for the diseases of the crops. Most of the proposed control agents are not fully satisfactory for the following reasons: their control effectiveness is insufficient; or their use is restricted due to the emergence of drug-resistant pathogenic bacteria; or they may cause phytotoxicity or pollution to the plant body ; Or the toxicity to humans, animals and fish or the impact on the environment. Therefore, there is a strong desire for a safe useable control agent with few such defects.

In addition, Patent Document 1 discloses a compound represented by formula (1) or formula (2). According to Patent Document 1, the compound appears to be useful as a complex II inhibitor of an electron transport system.

In addition, Non-Patent Document 1 discloses a compound represented by the formula (3). According to Non-Patent Document 1, this compound seems to be useful as an antimalarial agent.

In addition, Non-Patent Document 2 discloses a compound represented by the formula (4). According to Non-Patent Document 2, the compound appears to have a mammalian-bacterial complex II inhibitory activity.

[Patent Document 1] WO 2003/103667 A

[Non-Patent Document 1] J. Med. Chem. 2008, 51, 2845-2852

[Non-Patent Document 2] Bioorg. Med. Chem. Lett. 2010, 20, 1665-1668

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

In order to solve the problems described above, the present invention has been completed including the following aspects.

[1] A pyridine compound, an N-oxide compound thereof, or a tautomer or salt thereof, the pyridine compound is represented by formula (I),

In formula (I), R ¹ represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or G ¹ substituted C1 ~ 6 alkoxy, unsubstituted or G ¹ substituted C1 ~ 6 alkoxycarbonyl, unsubstituted or G ¹ substituted C1 ~ 6 alkylthio group, unsubstituted or G ¹ substituted C1 ~ 6 alkylaminocarbonyl, unsubstituted or G ² substituted C6 ~ 10 aryl, cyano or halogeno group; in formula (I), R ² 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 ² of C3 ~ 8 cycloalkyl, unsubstituted or C1 ~ 6 alkoxy substituted with G ¹ , methyloxy, unsubstituted or substituted G ^1-6 alkylcarbonyloxy, unsubstituted or substituted G ^2- C 6-10 aryl, (C1-C6 alkoxyimino group, unsubstituted or substituted with G ¹ ) -C1-6 alkyl group, 3 to 10-membered heterocyclic C1- 6 alkyl group, unsubstituted or G ² substituted, cyano Or a halogen group; in the formula (I), R ³ represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkene Group, unsubstituted or G ² substituted C3-8 cycloalkyl, unsubstituted or G ¹ substituted C1-6 alkoxy, unsubstituted or G ¹ substituted C1-6 alkylcarbonyl, C1 ~ 6 alkoxycarbonyl, unsubstituted or G ¹ substituted, carboxyl, formamyl, formamyloxy, unsubstituted or G ¹ substituted C1 ~ 6 alkylcarbonyloxy, unsubstituted or the G ² substituted by C6 ~ 10 aryl group, unsubstituted or substituted by the G ² 3 ~ 10 membered heterocyclic group, (unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxyimino group) -C1 ~ 6 alkyl, unsubstituted or G ¹ substituted mono C1 ~ 6 alkylamino, unsubstituted or G ¹ substituted C1 ~ 6 alkylamino, cyano or halogen group; formula (I ), R ⁴ represents a hydrogen atom, an unsubstituted or G ¹ -substituted C1 to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or G ¹ substituted C 2 to 6 6 alkynyl, unsubstituted or G ² substituted C3-8 cycloalkyl, unsubstituted or G ² substituted C6-10 aryl C1-6 alkyl, unsubstituted or G ² substituted 3 to 10-membered heterocyclic group C1 ~ 6 alkyl group, methyl acyl, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl carbonyl, unsubstituted or substituted with G ² of C3 ~ 8 cycloalkyl Group, unsubstituted or substituted with G ¹ of C2 ~ 6 alkenyl-carbonyl, unsubstituted or substituted with G ² of the C6 ~ 10 aryl-carbonyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxycarbonyl , unsubstituted or G ¹ of C2 ~ 6 alkenyl substituted oxycarbonyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkylsulfonyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl aminocarbonyl, unsubstituted or substituted with ¹ G of (C1 ~ 6 alkylthio) carbonyl group, ^a substituted or unsubstituted of C1 ~ 6 alkylamino (thiocarbonyl group) by G, or of formula (II), Of organic

In formula (II), * represents a bonding bond; in formula (II), G ^a each independently represents a hydrogen atom, an unsubstituted or G ¹ -substituted C1 to 6 alkyl group, unsubstituted or substituted with G ¹ C2 ~ 6 alkenyl, unsubstituted or G ¹ substituted C2 ~ 6 alkynyl, unsubstituted or G ² substituted C3 ~ 8 cycloalkyl, or unsubstituted or G ² substituted C6 ~ 10 aryl groups; in the formula (II), G ^b represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or substituted by G ¹ group of C2 ~ 6 alkynyl, unsubstituted or substituted with G ² of C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ² of the C6 ~ 10 aryl group, or unsubstituted or G ² Substituted 3 to 10-membered heterocyclic groups; in formula (II), T represents an oxygen atom, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio) carbonyl group, a carbonyl (thio) group, (Thio) carbonyloxy, oxycarbonyl (thio), or a divalent group represented by -OC (= O) -N (G ^b )-; in formula (I), A represents an oxygen atom or formula (III) Represents a divalent organic group;

In formula (III), * represents a bonding position; in formula (III), R ⁵ and R ⁶ each independently represent a hydrogen atom, an unsubstituted or G ¹ -substituted C1 to 6 alkyl group, an unsubstituted or G ¹ substituted C1 ~ 6 alkoxy, unsubstituted or G ² substituted C6 ~ 10 aryloxy, unsubstituted or G ¹ substituted alkoxycarbonyloxy, halo, hydroxyl; R ⁵ And R ⁶ may be connected to form a 3- to 6-membered ring together with the carbon atoms bonded to R ⁵ and R ⁶ ; in the formula (I), Cy represents an unsubstituted or G ² substituted C 6-10 aryl group, G ² substituted C3-8 cycloalkyl, unsubstituted or G ² substituted 3- to 10-membered heterocyclyl, or 13-membered heteroaryl; G ¹ represents hydroxyl, C1 to 6 alkoxy, and C1 to 6 Alkoxy C1 ~ 6 alkoxy, C1 ~ 6 alkoxycarbonyl, formamyloxy, C1 ~ 6 alkylcarbonyloxy, C1 ~ 6 alkoxycarbonyloxy, mono C1 ~ 6 alkoxycarbonyl Amine group, cyano group, amino group or halogen group; when there are two or more groups substituted with G ¹ , the G ¹ may be the same as or different from each other; G ² represents an unsubstituted or G ²¹ substituted group C1 ~ 8 alkyl, unsubstituted or substituted with the G ²¹ C2 ~ 6 alkenyl, unsubstituted or substituted with G ²¹ of C2 ~ 6 alkynyl group, a hydroxyl group, without A substituted or is substituted by G of ²¹ C1 ~ 6 alkoxy, methyl acyl, unsubstituted or substituted with G ²¹ of C1 ~ 6 alkyl carbonyl, unsubstituted or substituted with G ²¹ of C1 ~ 6 alkoxycarbonyl Methylformyloxy, unsubstituted or G ²¹ substituted C1 ~ 6 alkylcarbonyloxy, methylamino, unsubstituted or substituted with G ²¹ mono C1 ~ 6 alkylcarbonylamino, unsubstituted substituted or unsubstituted by the G ²¹ N- (C1 ~ 6 alkyl-carbonyl) -N- (C1 ~ 6 alkyl) amino, unsubstituted or substituted with the G ²¹ N- (C1 ~ 6 alkyl-carbonyl group) -N- (C1 ~ 6alkoxycarbonyl) amino, unsubstituted or substituted with G ²¹ C1 ~ 6alkoxycarbonyloxy, unsubstituted or substituted with G ²¹ mono C1 ~ 6 alkoxy carbonyl group, unsubstituted or substituted with the G ²² C3 ~ 8 cycloalkyl, unsubstituted or substituted by the G ²² C3 ~ 8 cycloalkenyl group, unsubstituted or substituted by G ²² of C3 ~ 8 cycloalkyl Carbonylcarbonylaminocarbonyl, unsubstituted or substituted with G ²² C6 ~ 10 aryl, unsubstituted or substituted with G ²² C6 ~ 10 aryl C2 ~ 6 alkynyl, unsubstituted or substituted with G ²² C6 ~ 10 aryloxy, unsubstituted or substituted with the G ²² 3 ~ 10 membered heterocyclic group, 13 heteroaryl, unsubstituted or substituted by the G ²² 3 ~ 10 membered heteroaryl epoxy , A mercapto group, unsubstituted or substituted with G ²¹ of C1 ~ 6 alkylthio, unsubstituted or substituted by G of ²¹ C1 ~ 6 alkylsulfinyl acyl, unsubstituted or substituted with the C1 ~ 6 G ²¹ Alkylsulfonyl, pentafluorosulfanyl group, unsubstituted or substituted with G ²² C6 ~ 10 arylthio, unsubstituted or substituted with G ²² C6 ~ 10 arylsulfinyl, the unsubstituted or substituted by G ²² C6 ~ 10 aryl sulfonic acyl, unsubstituted or substituted with the single G ²² C6 ~ 10 aryl group, two hydroxyl groups boron (dihydroboryl group), a nitro group, a cyano Group, halo group, unsubstituted or substituted with G ²¹ C1-6 alkylene group, unsubstituted or substituted with G ²¹ C1-6 alkylene monooxy, unsubstituted or substituted with G ^21- substituted C1 ~ 6 alkylene dioxy, -CR ^a = NR ^b represents the group; here, R ^a represents a hydrogen atom, C1 ~ 6 alkyl, unsubstituted or mono-C1 ~ substituted with G ²¹ 6 alkylcarbonylamino, or mono-C3-8 cycloalkylcarbonylamino unsubstituted or substituted with G ²² , R ^b represents unsubstituted or G ²¹ substituted C1-6 alkoxy, unsubstituted or substituted of G ²² C3 ~ 8 cycloalkyl group, the unsubstituted or substituted by G ²² Phenoxy, unsubstituted or G ²¹ mono-C1 ~ 6 alkylamino group, or unsubstituted or G ^21- substituted C1 ~ 6 alkylamino group; exists in the G ² substituted group 2 In more than one case, the G ² may be the same as or different from each other; G ²¹ represents a C1 to 6 alkoxy group, a C1 to 6 halogenated alkoxy group, a mono C1 to 6 alkylamino group, and a di C1 to 6 alkyl group Amine, mono (C1 ~ 6alkoxyC1 ~ 6alkylcarbonyl) amino, unsubstituted or substituted with G ²¹¹ C6 ~ 10 aryl, unsubstituted or substituted with G ²¹¹ C6 ~ 10 aryloxy group, unsubstituted or substituted with the G ²¹¹ 3 ~ 10 membered heterocyclic group, unsubstituted or substituted with the G ²¹¹ 3 ~ 10 membered heterocyclic group or a halogen group; the substituent on the group by the presence of two G ²¹ In the above cases, the G ²¹ may be the same as or different from each other; G ²¹¹ represents a C1 to 6 alkyl group, a C1 to 6 halogenated alkyl group, a C1 to 6 alkoxy group, a C1 to 6 halogenated alkoxy group, or a halogen group; When there are two or more groups substituted by G ²¹¹ , the G ²¹¹ may be the same as or different from each other; G ²² represents an unsubstituted or hydroxy-substituted C1 to 6 alkyl group, C1 to 6 halogenated alkyl group, C2 ~ 6 alkenyl, C2 ~ 6 halogenated alkenyl, C2 ~ 6 alkynyl, C1 ~ 6 alkoxy, C1 ~ 6 halogenated alkoxy C1 ~ 6 alkylcarbonyl, mono C1 ~ 6 alkylamino, di C1 ~ 6 alkylamino, C1 ~ 6 alkylamino carbonyl, C1 ~ 6 alkylthio, C1 ~ 6 halogenated alkylthio, C1 ~ 6 alkylsulfinyl sulfenyl, C1 ~ 6 halogenated alkylsulfinyl sulfonyl, C1 ~ 6 alkylsulfinyl sulfonyl, C1 ~ 6 halogenated alkylsulfinyl sulfonyl, C3 ~ unsubstituted or substituted with G ²²¹ ~ 8 cycloalkyl, unsubstituted or substituted with G ²²¹ C3 ~ 8 cycloalkyl C1 ~ 6 alkyl, unsubstituted or substituted with G ²²¹ C6 ~ 10 aryl, unsubstituted or substituted with G ²²¹ 3- to 10-membered heterocyclyl, 3 to 10-membered heterocyclyl, unsubstituted or substituted with G ^{221 211} group of substituted C1 ~ 6 alkylene dioxy group, or -CR ^c = NOR ^d represents the; here, R ^c represents a C1 ~ 6 alkyl group, R ^d represents an unsubstituted or substituted by C3 ~ G ²²¹ of 8 cycloalkyl; when there are two or more groups substituted by G ²² , the G ²² may be the same as or different from each other; G ²²¹ represents a C1 to 6 alkyl group, a C1 to 6 halogenated alkyl group, and C1 to 6 alkoxy group, a halogenated C1 ~ 6 alkoxy group, mono C1 ~ 6 alkylamino, di-C1 ~ 6 alkyl group, C6 ~ 10 aryl group or a halogen group; the substituent on the group by the presence of G ²²¹ 2 When the above case, the G ²²¹ to each other may be the same or different.

[2] An agricultural and horticultural fungicide containing at least one selected from the group consisting of a pyridine compound according to the above [1], an N-oxide compound thereof, and a tautomer and a salt thereof as an active ingredient .

[3] A pest control agent comprising, as an active ingredient, at least one selected from the group consisting of a pyridine compound according to the above [1], an N-oxide compound thereof, and a tautomer and a salt thereof.

[4] An insecticidal or acaricide containing at least one selected from the group consisting of a pyridine compound according to the above [1], an N-oxide compound thereof, and a tautomer and a salt thereof as effective ingredient.

[5] An external parasite controlling agent containing at least one selected from the group consisting of a pyridine compound according to the above [1], an N-oxide compound thereof, and a tautomer and a salt thereof as an active ingredient .

The pyridine compound of the present invention is a novel compound that has the effects of pest control, sterilization, acaricide, insecticide, etc., does not cause phytotoxicity to plants, has little toxicity to humans, animals, fishes, and the environment. In particular, it shows excellent control effects on wheat diseases. The pyridine compound of the present invention is useful as an active ingredient of agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides.

The pyridine compound of the present invention is a pyridine compound represented by formula (I) (hereinafter sometimes referred to as compound (I)), its N-oxide compound, a tautomer of compound (I), or a salt of compound (I).

First, the groups G ¹ and G ² which may substitute a group in the formula (I) will be described.

[G ¹ ]

The substituent G ¹ represents a hydroxyl group, a C1 to 6 alkoxy group, a C1 to 6 alkoxy group, a C1 to 6 alkoxy group, a C1 to 6 alkoxycarbonyl group, a methylamino group, a C1 to 6 alkylcarbonyloxy group, and C1 ~ 6 alkoxycarbonyloxy, mono-C1 ~ 6 alkoxycarbonylamino, cyano, amine, or halogen. When there are two or more groups substituted with G ¹ , the G ¹ may be the same as or different from each other.

Examples of C1 to 6 alkoxy include methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexyloxy, isopropoxy, isobutoxy, and secondary Butoxy, tertiary butoxy, isohexyloxy and the like.

Examples of the C1 to 6 alkoxy C1 to 6 alkoxy include methoxymethoxy, 1-methoxyethoxy, and 2-methoxyethoxy.

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

Examples of the C1 to C6 alkylcarbonyloxy group include ethoxyl, propionyloxy, and butyloxy.

Examples of C1 to 6 alkoxycarbonyloxy include methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, isopropoxycarbonyloxy, and n-butoxycarbonyloxy. And tertiary butoxycarbonyloxy.

The mono-C1 ~ 6 alkoxycarbonylamino group is a mono-substituted C1 ~ 6 alkoxycarbonyl group on the amine group. Examples of the C1 to 6 alkoxycarbonylamino group include a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, an isopropoxycarbonylamino group, and an n-butoxycarbonylamine group. And tertiary butoxycarbonylamino groups.

Examples of the halogen group include a fluoro group, a chloro group, a bromo group, and an iodo group.

G ^{1 is} preferably a hydroxyl group, a C1 to 6 alkoxy group, or a halogen group.

[G ² ]

G ² represents an unsubstituted or G ²¹ substituted C1-8 alkyl group, an unsubstituted or G ²¹ substituted C2-6 alkenyl group, an unsubstituted or G ²¹ substituted C2-6 alkynyl group, a hydroxyl group, Unsubstituted or G ²¹ substituted C1 ~ 6 alkoxy, formamyl, unsubstituted or G ²¹ substituted C1 ~ 6 alkylcarbonyl, unsubstituted or G ²¹ substituted C1 ~ 6 alkoxy Carbonyl, methylamino, unsubstituted or G ²¹ substituted C1 ~ 6 alkylcarbonyloxy, methylamino, unsubstituted or G ²¹ substituted mono C1 ~ 6 alkylcarbonylamino , unsubstituted or substituted with the G ²¹ N- (C1 ~ 6 alkyl-carbonyl) -N- (C1 ~ 6 alkyl) amino, unsubstituted or substituted with the N- G ²¹ (C1 ~ 6 alkyl (Carbonyl) -N- (C1 ~ 6alkoxycarbonyl) amino, unsubstituted or substituted with G ²¹ C1 ~ 6alkoxycarbonyloxy, unsubstituted or substituted with G ²¹ mono C1 ~ 6 alkyl Oxycarbonylamino, unsubstituted or substituted with G ²² C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ²² C3 ~ 8 cycloalkenyl, unsubstituted or substituted with G ²² C3 ~ 8 cycloalkylcarbonyl aminocarbonyl, unsubstituted or substituted by G ²² of the C6 ~ 10 aryl group, unsubstituted or substituted by G ²² C6 ~ 10 aryl group of C2 ~ 6 alkynyl group, without Or substituted on behalf of G ²² C6 ~ 10 aryloxy, unsubstituted or substituted with the G ²² 3 ~ 10 membered heterocyclic group, 13 heteroaryl, unsubstituted or substituted by the G ²² 3 ~ 10 membered Heterocyclyloxy, mercapto, unsubstituted or substituted with C ²¹ ~ 6 alkylthio, unsubstituted or substituted with G ²¹ alkyl sulfinyl sulfenyl, unsubstituted or substituted with G ²¹ C1 ~ 6 alkylsulfonyl, pentafluorothio, unsubstituted or substituted with G ²² C6 ~ 10 arylthio, unsubstituted or substituted with G ²² C6 ~ 10 arylsulfinyl, the unsubstituted or substituted by G ²² C6 ~ 10 aryl sulfonic acyl, unsubstituted or substituted with the single G ²² C6 ~ 10 aryl group, di boron hydroxyl group, a nitro group, a cyano group, a halogen group , Unsubstituted or substituted with G ²¹ C1 ~ 6 alkylene, unsubstituted or substituted with G ²¹ C1 ~ 6 alkyl monooxy, unsubstituted or substituted with G ²¹ C1 ~ 6 alkylene Dioxy, -CR ^a = NR ^b .

Here, R ^a represents a hydrogen atom, a C1 to 6 alkyl group, a mono-C1 to 6 alkylcarbonylamino group which is unsubstituted or substituted with G ²¹ , or a mono C3 to 8 cycloalkane group which is unsubstituted or substituted with G ²² Carbonylamino, R ^b represents an unsubstituted or G ²¹ substituted C1-6 alkoxy group, an unsubstituted or G ²² substituted C3-8 cycloalkoxy group, an unsubstituted or G ²² substituted phenoxy, unsubstituted or substituted with G ²¹ of the single-C1 ~ 6 alkyl group, or an unsubstituted or substituted bis G ²¹ C1 ~ 6 alkyl group. When there are two or more groups substituted with G ² , the G ² may be the same as or different from each other.

C1 ~ 6 alkoxy, C1 ~ 6 alkoxycarbonyl, C1 ~ 6 alkylcarbonyloxy, C1 ~ 6 alkoxycarbonyloxy, mono C1 ~ 6 alkoxycarbonylamino in substituent G ² , And halogen groups are as described.

The C1-8 alkyl group may be a straight chain, and if the carbon number is 3 or more, it may be branched. Examples of the C1-6 alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, secondary butyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl, and iso Amyl, neopentyl, 2-methylbutyl, 2,2-dimethylpropyl, isohexyl, n-heptyl, n-octyl and the like.

Examples of C2-6 alkenyl include vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, and 1-methyl Vinyl (isopropenyl), 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentene Base, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5- Hexenyl and the like.

Examples of C2-6 alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and 1-methyl-2- 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.

The C1 ~ 6 alkylcarbonyl group is a group in which the C1 ~ 6 alkyl group described above is bonded to the carbonyl group. Examples of the C1 to C6 alkylcarbonyl group include an ethylfluorenyl group, a propylfluorenyl group, a butylfluorenyl group, an isobutylfluorenyl group, and a trimethylethylfluorenyl group.

The mono-C1-6 alkylcarbonylamino group is a mono-substituted C1-6 alkylcarbonyl group on the amine group. Examples of the mono-C1-6 alkylcarbonylamino group include an ethylamino group, a propylamino group, a butylamino group, an isopropylcarbonylamino group, a 2,2-dimethylpropylcarbonylamino group, and the like. .

N- (C1 ~ 6alkylcarbonyl) -N- (C1 ~ 6alkyl) amino group is substituted on the amine group with the above-mentioned C1 ~ 6alkyl group and C1 ~ 6alkylcarbonyl group. Examples of the N- (C1-6 alkylcarbonyl) -N- (C1-6 alkyl) amino group include N- (2,2-dimethylpropylcarbonyl) -N-methylamino group.

N- (C1 ~ 6 alkylcarbonyl) -N- (C1 ~ 6 alkoxycarbonyl) amino group is substituted on the amine group with the above-mentioned C1 ~ 6 alkoxycarbonyl group and C1 ~ 6 alkylcarbonyl group By. Examples of the N- (C1 to 6 alkylcarbonyl) -N- (C1 to 6 alkoxycarbonyl) amino group include N-ethylfluorenyl-N-methoxycarbonylamino group.

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

Examples of the C3 to 8 cycloalkenyl include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like.

Examples of the C3-8 cycloalkylcarbonylaminocarbonyl group include a group represented by the following formula. ＊ indicates the bonding position.

The C6-10 aryl group may be any of a monocyclic ring and a polycyclic ring. If at least one ring in the polycyclic aryl group is an aromatic ring, the remaining rings may be any of a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the C6-10 aryl group include a phenyl group, a naphthyl group, a fluorenyl group, an indenyl group, a dihydroindenyl group, and a tetrahydronaphthyl group.

C6 ~ 10 aryl C2 ~ 6 alkynyl is substituted on the C2 ~ 6 alkynyl group described above with the C6 ~ 10 aryl group described above. Examples of the C6 to 10 aryl C2 to 6 alkynyl group include phenylethynyl and the like.

The C6 ~ 10 aryloxy group is substituted on the hydroxyl group with the C6 ~ 10 aryl group described above. Examples of the C6 to 10 aryloxy group include a phenoxy group and a naphthyloxy group.

The 3- to 10-membered heterocyclic group contains a cyclic group having 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as the constituent atoms of the ring. The heterocyclic group may be any of a monocyclic ring and a polycyclic ring. If at least one ring of the polycyclic heterocyclic group is a heterocyclic group, the remaining rings 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 aziridinyl, oxiranyl group, azetidinyl group, oxetanyl group, and pyrrolidine Tetrahydrofuranyl, tetrahydrothiazolyl, piperidinyl, piperidinyl base, Phosphono, tetrahydropyranyl, dioxolanyl group, dioxanyl group, iso Isoxazolidinyl group, 3-oxa Amidazinyl, 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl (4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl group) and the like.

Examples of the 5-membered heteroaryl group include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, Oxazolyl, iso Oxazolyl, thiazolyl, isothiazolyl, triazolyl, Diazolyl, thiadiazolyl, tetrazolyl, and the like.

Examples of the 6-membered heteroaryl group include pyridyl, pyridine Base, pyrimidinyl, Base, three Base etc.

Examples of 5- to 6-membered unsaturated heterocyclic groups include dihydroiso Azole and others.

Examples of the 9-membered heteroaryl include indolyl, isoindolyl, benzofuranyl, dihydrobenzofuranyl, indazolyl, and benzo. Oxazolyl An oxazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a pyridylpyrazolyl group, a triazolopyridyl group, and the like.

Examples of the 9-membered partially unsaturated heterocyclic group include an indololinyl group, an isoindolinyl group, and a 1,3-dioxoisoindolinyl group.

Examples of the 10-membered heteroaryl group include quinolinyl, isoquinolinyl, Phenyl Quinolyl Phenyl and so on.

Examples of the 13-membered heteroaryl group include dibenzo [b, d] furanyl, dibenzo [b, d] thienyl, and the like.

The 3- to 10-membered heterocyclooxy group is substituted on the hydroxyl group with the 3- to 10-membered heterocyclic group described above. Examples of the 3- to 10-membered heterocyclic oxy group include pyrazolyloxy and pyridyloxy. The 3 to 10-membered heterocyclic oxy group is preferably a 5 to 6-membered heterocyclic oxy group.

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

The C1-6 alkylsulfinyl sulfenyl group is substituted on the sulfinyl sulfinyl group with the C1-6 alkyl group described above. Examples of the C1-6 alkylsulfinylsulfenyl group include a methylsulfinylsulfonyl group, an ethylsulfinylsulfinyl group, and a tertiary butylsulfinylsulfinyl group.

The C1 ~ 6 alkylsulfonyl group is substituted on the sulfonyl group with the C1 ~ 6 alkyl group described above. Examples of the C1-6 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, and a tertiary butylsulfonyl group.

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

C6 ~ 10 arylsulfinyl is substituted on the sulfinyl with the C6 ~ 10 aryl described above. Examples of the C6 to 10 arylsulfinyl sulfenyl group include a phenylsulfinyl sulfinyl group, a naphthylsulfinyl sulfinyl group, and the like.

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

The C6 ~ 10 arylamino group is substituted on the amine group with the C6 ~ 10 aryl group described above. Examples of the C6 to 10 arylamino group include a phenylamino group and the like.

The C1 ~ 6 alkylene group is a divalent group obtained by removing two hydrogen atoms in a C1 ~ 6 alkane. Examples of the C1 to 6 alkylene group include a methylene group, an ethylene group (dimethylene group), a trimethylene group, a tetramethylene group, and a propane-1,2-diyl group (that is, a propylene group). Examples of the C6 to 10 aryl group substituted with a C1 to 6 alkylene group as G ² include 2,3-dihydro-1H-indenyl, 5,6,7,8-tetranaphthyl and the like.

The C1 ~ 6 alkylene monooxy group is a divalent group in which one hydrogen atom in a C1 ~ 6 alkane is substituted with an oxy group. Examples of the C1 to 6 alkylene monooxy group include a methylene monooxy group (-CH ₂ O-), an ethylene monooxy group (-CH ₂ CH ₂ O-), and a trimethylene monooxy group. (-CH ₂ CH ₂ CH ₂ O-) and the like. Examples of the C6-10 aryl group substituted with a C1-6 alkylene monooxy group as G ² include 2,3-dihydrobenzofuranyl, Base etc.

C1 ~ 6 alkylene dioxy is a divalent group in which two hydrogen atoms in a C1 ~ 6 alkane are substituted with an oxy group. Examples of the C1 to 6 alkylene dioxy group include a methylene dioxy group (-OCH ₂ O-), an ethylene dioxy group (-OCH ₂ CH ₂ O-), and a trimethylene dioxy group. Wait. Examples of the C6-10 aryl group substituted with a C1-6 alkylene dioxy group as G ² include 2,3-dihydro-benzo [1,4] dihydrocarbyloxy (2,3-dihydro -benzo [1,4] dioxyl group), benzo [1,3] dioxolyl group, and the like.

The formula: -CR ^a = NR ^b , the C1 ~ 6 alkyl group and mono C1 ~ 6 alkylcarbonylamino group in R ^a are as described above.

Examples of the mono-C3-8 cycloalkylcarbonylamino group in R ^a include a cyclopropylcarbonylamino group, a cyclobutylcarbonylamino group, a cyclopentylcarbonylamino group, a cyclohexylcarbonylamino group, and the like.

Formula: -CR ^a = NR ^b The C1 ~ 6 alkoxy group and C3 ~ 8 cycloalkoxy group in R ^b in the group represented by those are as already described.

Examples of the mono-C 1 to 6 alkylamino group in R ^b include a methylamino group and an ethylamino group.

Examples of the C1-C6 alkylamino group in ^Rb include a dimethylamino group and a diethylamino group.

[G ²¹ ]

G ²¹ represents C1 to 6 alkoxy, C1 to 6 halogenated alkoxy, mono C1 to 6 alkylamino, di C1 to 6 alkylamino, mono (C1 to 6 alkoxyC1 to 6 alkylcarbonyl ) Amine, unsubstituted or substituted with G ²¹¹ C6 ~ 10 aryl, unsubstituted or substituted with G ²¹¹ C6 ~ 10 aryloxy, unsubstituted or substituted with G ²¹¹ 3 to 10 membered heterocyclic ring 3 to 10 membered heterocyclic oxy or halo, unsubstituted or substituted with G ²¹¹ . When there are two or more groups substituted with G ²¹ , the G ²¹ may be the same as or different from each other.

C1 ~ 6 alkoxy, C6 ~ 10 aryl, mono C1 ~ 6 alkylamino, di C1 ~ 6 alkylamino, C6 ~ 10 aryloxy, 3 ~ 10 member heterocyclic ring in substituent G ²¹ The radicals, 3 to 10-membered heterocyclooxy, and halogen radicals are as described above.

The C1 ~ 6 halogenated alkoxy group is a halogen group substituted on the C1 ~ 6 alkoxy group described above.

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

Examples of the mono (C1 ~ 6alkoxyC1 ~ 6alkylcarbonyl) amino group include a methoxymethylcarbonylamino group, an ethoxymethylcarbonylamino group, and a 2-methoxyethylcarbonylamino group , 2-ethoxyethylcarbonylamino and the like.

G ^{21 is} preferably a halogen group.

[G ²¹¹ ]

G ²¹¹ represents a C1 to 6 alkyl group, a C1 to 6 halogenated alkyl group, a C1 to 6 alkoxy group, a C1 to 6 halogenated alkoxy group, or a halogen group. When two or more groups substituted by G ²¹¹ exist, the G ²¹¹ may be the same as or different from each other.

The C1 ~ 6 alkyl group, C1 ~ 6 alkoxy group, C1 ~ 6 halogenated alkoxy group, and halogen group in G ²¹¹ are as described above.

The C1 ~ 6 haloalkyl group is a halogen group substituted on the C1 ~ 6 alkyl group described above. Examples of the C1 to 6 halogenated alkyl group include fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, dibromomethyl, trifluoromethyl, trichloromethyl, and tribromo. 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.

G ^{211 is} preferably a C1 to 6 alkyl group, and particularly preferably a methyl group.

[G ²² ]

G ²² represents unsubstituted or hydroxy-substituted C1 ~ 6 alkyl, C1 ~ 6 halogenated alkyl, C2 ~ 6 alkenyl, C2 ~ 6 halogenated alkenyl, C2 ~ 6 alkynyl, C1 ~ 6 alkoxy, C1 ~ 6 halogenated alkoxy, C1 ~ 6 alkylcarbonyl, mono C1 ~ 6 alkylamino, di C1 ~ 6 alkylamino, C1 ~ 6 alkylamino carbonyl, C1 ~ 6 alkylthio, C1 ~ 6 haloalkylthio, C1 ~ 6 alkylsulfinamilide, C1 ~ 6 haloalkylsulfinamido, C1 ~ 6 alkylsulfofluorenyl, C1 ~ 6 haloalkylsulfinyl, unsubstituted or substituted of G ²²¹ C3 ~ 8 cycloalkyl, unsubstituted or substituted by the G ²²¹ C3 ~ 8 cycloalkyl, C1 ~ 6 alkyl, the unsubstituted or substituted by G ²²¹ C6 ~ 10 aryl group, an 3- to 10-membered heterocyclyl substituted or substituted with G ²²¹ , 3- to 10-membered heterocyclyl substituted or unsubstituted or substituted with G ²²¹ , pentafluorothio, nitro, cyano, halogen, pendant oxygen Group, C1-C6 alkylenedioxy group which is unsubstituted or substituted with G ²¹¹ , or a group represented by -CR ^c = NOR ^d . Here, R ^c represents a C1 to 6 alkyl group, and R ^d represents a C3 to 8 cycloalkyl group which is unsubstituted or substituted with G ²²¹ . When there are two or more groups substituted with G ²² , the G ²² may be the same as or different from each other.

C1 ~ 6 alkyl, C1 ~ 6 halogenated alkyl, C2 ~ 6 alkenyl, C2 ~ 6 alkynyl, C1 ~ 6 alkoxy, C1 ~ 6 halogenated alkoxy, C1 ~ 6 alkyl in substituent G ²² Carbonyl group, mono-C1 ~ 6 alkylamino group, di-C1 ~ 6 alkylamino group, C1 ~ 6 alkylthio group, C1 ~ 6 alkylsulfinamilide group, C1 ~ 6 alkylsulfonyl group, C3 ~ 8 The cycloalkyl group, C6-10 aryl group, 3-10 member heterocyclic group and halogen group, and C1-6 alkylene dioxy group are as described above.

The C2 ~ 6 halogenated alkenyl group is a halogen group substituted on the C1 ~ 6 alkenyl group already described. Examples of C2 to 6 halogenated alkenyl include 2-chlorovinyl, 2-bromovinyl, 2-iodovinyl, 1-fluoro-2-iodovinyl, 2-chloro-1-propenyl, 2- Fluoro-1-butenyl and the like.

Examples of the C3-8 cycloalkyl C1-6 alkyl include cyclopropylmethyl, 2-cyclopropylethyl, cyclopentylmethyl, 2-cyclohexylethyl, and 2-cyclooctylethyl Wait.

Examples of the C1 to 6 alkylaminocarbonyl group include a methylaminocarbonyl group, a dimethylaminocarbonyl group, and a diethylaminocarbonyl group.

The C1 ~ 6 halogenated alkylthio group is a halogen group substituted on the C1 ~ 6 alkylthio group described above. Examples of the C1 to 6 halogenated alkylthio group include trifluoromethylthio group and the like.

The C1 ~ 6 halogenated alkylsulfinyl sulfenyl group is substituted with the halogen group in the C1 ~ 6 alkyl sulfinyl sulfinyl group already described. Examples of the C1 to 6 halogenated alkylsulfinyl sulfenyl group include trifluoromethylsulfinyl sulfinyl group and the like.

The C1 ~ 6 halogenated alkylsulfonyl group is a halogen group substituted on the C1 ~ 6 alkylsulfonyl group described above. Examples of the C1 to 6 halogenated alkylsulfonyl groups include trifluoromethylsulfonyl groups and the like.

The 3- to 10-membered heterocyclic carbonyl group is substituted with the 3- to 10-membered heterocyclic group described above on the carbonyl group. Examples of the 3 to 10-membered heterocyclic carbonyl group include azetidinylcarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl, Phenylcarbonyl, piperazine Carbonyl, 1,4-dioxane carbonyl, nitrogen Azepanylcarbonyl group, 1,4-diazepine Carbonyl, pyrrolylcarbonyl, thiazolylcarbonyl, pyridylcarbonyl, tetrahydropyridylcarbonyl, tetrahydropyranylcarbonyl, tetrahydrofurylcarbonyl, tetrahydroisoquinolinylcarbonyl, decahydroisoquinolinylcarbonyl, and the like. The 3- to 10-membered heterocyclic carbonyl group is preferably a 5- to 6-membered heterocyclic carbonyl group.

Formula: -CR ^c = NOR ^d The C1 ~ 6 alkyl group in R ^c in the group represented is as already described.

Formula: -CR ^c = NOR ^d The C3 ~ 8 cycloalkyl group in R ^d in the base is as already described.

Examples of the C 3 to 8 cycloalkyl or C 3 to 8 cycloalkenyl substituted with a pendant oxygen group or an alkylene dioxy group as G ²² include the following groups. ＊ indicates the bonding position.

The 3- to 10-membered heterocyclic group in G ²² is preferably a 5- to 6-membered heterocyclic group.

As G ²² , an unsubstituted or hydroxy-substituted C1 to 6 alkyl group, C1 to 6 halogenated alkyl group, C2 to 6 alkenyl group, C2 to 6 alkynyl group, C1 to 6 alkoxy group, and C1 to 6 are preferable. Halogenated alkoxy, C1 ~ 6 alkylcarbonyl, diC1 ~ 6 alkylamino, C1 ~ 6 alkylaminocarbonyl, C1 ~ 6 alkylthio, C1 ~ 6 halogenated alkylthio, C1 ~ 6 alkyl Sulfinylene, C1 ~ 6 halogenated alkylsulfinyl, C1 ~ 6 alkylsulfinyl, C1 ~ 6 halogenated alkylsulfinyl, C3 ~ 8 cycloalkyl unsubstituted or substituted with G ²²¹ , Unsubstituted or substituted with G ²²¹ C6 ~ 10 aryl, unsubstituted or substituted with G ²²¹ 3- to 10-membered heterocyclyl, unsubstituted or substituted with G ²²¹ 3- to 10-membered heterocyclyl carbonyl , Pentafluorothio, nitro, cyano, halogen, pendant oxy, unsubstituted or substituted with G ²¹¹ C1-6 alkylenedioxy, -CR ^c = NOR ^d , more preferably C1 ~ 6 alkyl, C1 ~ 6 halogenated alkyl, C1 ~ 6 alkoxy, C1 ~ 6 halogenated alkoxy, C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ²²¹ , unsubstituted or modified G ²²¹ substituted C6 ~ 10 aryl, unsubstituted or substituted 3 ~ 10 membered heterocyclic group with G ²²¹ , particularly preferably C1 ~ 6 alkyl, C1 ~ 6 haloalkyl, unsubstituted or G ²²¹ Replace Cyclohexyl, unsubstituted or substituted with G ²²¹ , unsubstituted or substituted with G ²²¹ 5-membered heterocyclic group (preferably tetrahydropyranyl, (Phenyl, dioxolyl, furyl, thienyl, pyrazolyl, pyridyl).

[G ²²¹ ]

G ²²¹ represents C1 to 6 alkyl, C1 to 6 halogenated alkyl, C1 to 6 alkoxy, C1 to 6 halogenated alkoxy, mono C1 to 6 alkylamino, di C1 to 6 alkylamino, C6 ~ 10 aryl or halo. When there are more than two groups substituted by G ²²¹ , the G ²²¹ may be the same as or different from each other.

C1 ~ 6 alkyl, C1 ~ 6 halogenated alkyl, C1 ~ 6 alkoxy, C1 ~ 6 halogenated alkoxy, mono C1 ~ 6 alkylamino, di C1 ~ 6 alkylamine in substituent G ²²¹ The radicals, C6-10 aryl, and halogen radicals are as described above.

G ^{221 is} preferably a C1 to 6 alkyl group, a C1 to 6 halogenated alkyl group, a C1 to 6 alkoxy group, a C1 to 6 halogenated alkoxy group, or a halogen group, particularly preferably a methyl group, a trifluoromethyl group, and a chloro group base.

[R ¹ ]

R ¹ represents a hydrogen atom, an unsubstituted or G ¹ substituted C1 to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or G ¹ substituted C ¹ to 6 alkoxy group Group, unsubstituted or G ¹ substituted C1 ~ 6 alkoxycarbonyl group, unsubstituted or G ¹ substituted C1 ~ 6 alkylthio group, unsubstituted or G ¹ substituted C1 ~ 6 alkylamine Carbonyl, unsubstituted or G ² substituted C6 ~ 10 aryl, cyano or halogen.

R ¹ is the C1 ~ 6 alkyl, C2 ~ 6 alkenyl group, C1 ~ 6 alkoxy, C1 ~ 6 alkoxycarbonyl, C1 ~ 6 alkylthio, C1 ~ 6 alkyl-carbonyl group, C6 ~ 10 The aryl group, the halogen group, the substituent G ¹ and the substituent G ² are as described above.

As R ¹ , an unsubstituted or G ¹ -substituted C1-6 alkyl group (preferably unsubstituted) or a halogen group is preferable, and a methyl group or a halogen group is particularly preferable.

[R ² ]

R ² in formula (I) represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or G ² substituted the C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxy, carboxylic acyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkylcarbonyloxy, unsubstituted Or C6 ~ 10 aryl substituted with G ² (C1 ~ 6 alkoxyimino substituted or substituted with G ¹ ) -C1 ~ 6 alkyl, 3 ~ unsubstituted or substituted with G ² 10-membered heterocyclic C1-6 alkyl, cyano or halogen.

R ² in the C1 ~ 6 alkyl, C2 ~ 6 alkenyl, C3 ~ 8 cycloalkyl, C1 ~ 6 alkoxy, C1 ~ 6 alkyl-carbonyl group, C6 ~ 10 aryl group, a halogen group, a substituted group G ¹ and the substituent G ² are as described above.

Examples of (C1 to 6 alkoxyimino) -C1 to 6 alkyl include methoxyimino-methyl, 1- (ethoxyimino) -ethyl, and the like.

The 3 to 10-membered heterocyclyl C1 to 6 alkyl is substituted on the C1 to 6 alkyl with the 3 to 10 membered heterocyclyl described above. As the 3- to 10-membered heterocyclyl C1-6 alkyl group, preferred examples include tetrahydrofurylmethyl, tetrahydropyranylmethyl, dioxolylmethyl, dioxolylmethyl, and pyridine. Azolylmethyl, pyridylmethyl and the like. The 3 to 10-membered heterocyclyl C1 to 6 alkyl group is preferably a 5 to 6-membered heterocyclyl C1 to 6 alkyl group.

As R ^2, it is preferably unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl group (preferably unsubstituted), or halogen group, more preferably is unsubstituted or substituted by G ¹ of C1 ~ 6 alkyl (Preferably unsubstituted), particularly preferably methyl.

[R ³ ]

In the formula (I), R ³ represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or G ² substituted the C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxy, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl-carbonyl group, an unsubstituted or substituted by C1 of G ¹ 1-6 alkoxycarbonyl, carboxyl, acyl, carboxylic acyl group, unsubstituted or substituted with G ¹ of a C1 ~ 6 alkylcarbonyloxy, unsubstituted or substituted with G ² of the C6 ~ 10 aryl group , unsubstituted or substituted with G ² of the 3 to 10-membered heterocyclic group, (unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxyimino group) -C1 ~ 6 alkyl group, unsubstituted or G ¹ substituted mono C1-6 alkylamino, unsubstituted or G ¹ substituted C1-6 alkylamino, cyano or halogen.

In R ³ of C1 ~ 6 alkyl, C2 ~ 6 alkenyl, C3 ~ 8 cycloalkyl, C1 ~ 6 alkoxy, C1 ~ 6 alkylcarbonyl group, C1 ~ 6 alkoxycarbonyl, C1 ~ 6 alkyl Carbonyloxy, C6 ~ 10 aryl, 3 ~ 10 member heterocyclic group, (C1 ~ 6 alkoxyimino) -C1 ~ 6 alkyl, mono C1 ~ 6 alkylamino, di C1 ~ 6 alkane The aminoamino group, the halogen group, the substituent G ¹ and the substituent G ² are as described above.

The 3- to 10-membered heterocyclic group in R ³ is preferably a 5- to 6-membered heteroaryl group.

As R ³ , an unsubstituted or G ¹ substituted C1-6 alkyl group, an unsubstituted or G ¹ substituted C1-6 alkoxycarbonyl group, a carboxyl group, an unsubstituted or G ² substituted C3 ~ 8 cycloalkyl, unsubstituted or G ² substituted 3 to 10 membered heterocyclic group, unsubstituted or G ¹ substituted C ¹ to 6 alkylamino group, more preferably unsubstituted or substituted G ¹ substituted C1-6 alkyl, unsubstituted or G ² substituted C3-8 cycloalkyl (preferably unsubstituted), unsubstituted or G ² substituted 3-10 membered heterocyclic group , unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl group (preferably unsubstituted), and particularly preferably an unsubstituted or substituted G ¹ (preferably halo-yl) alkyl group of C1 ~ 6 .

[R ⁴ ]

R ⁴ in formula (I) represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or G ¹ substituted C2 ~ 6 alkynyl, unsubstituted or G ² substituted C3 ~ 8 cycloalkyl, unsubstituted or G ² substituted C6 ~ 10 aryl C1 ~ 6 alkyl, unsubstituted or G ² Substituted 3 to 10-membered heterocyclyl C1 to 6 alkyl, formamyl, unsubstituted or G ¹ substituted C ¹ to 6 alkyl carbonyl, unsubstituted or G ² substituted C 3 to 8 cycloalkyl Carbonyl, unsubstituted or G ¹ substituted C2-6 alkenylcarbonyl, unsubstituted or G ² substituted C6-10 arylcarbonyl, unsubstituted or G ¹ substituted C1-6 alkoxycarbonyl , unsubstituted or G ¹ of C2 ~ 6 alkenyl substituted oxycarbonyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkylsulfonyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl aminocarbonyl, unsubstituted or substituted with ¹ G of (C1 ~ 6 alkylthio) carbonyl group, ^a substituted or unsubstituted of C1 ~ 6 alkylamino (thiocarbonyl group) by G, or of formula (II), Of its organic base.

Of R ^{4 is} C1 ~ 6 alkyl, C2 ~ 6 alkenyl group, C2 ~ 6 alkynyl group, C3 ~ 8 cycloalkyl, C6 to 10 aryl group C1 ~ 6 alkyl, 3 to 10-membered heterocyclic group C1 ~ 6 Alkyl, C1 ~ 6 alkylcarbonyl, C1 ~ 6 alkoxycarbonyl, C1 ~ 6 alkylsulfonyl, C1 ~ 6 alkylaminocarbonyl, substituent G ¹ and substituent G ² are as described above .

The C3 ~ 8 cycloalkylcarbonyl group is a carbonyl group substituted with 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.

The C2-6 alkenylcarbonyl group is a carbonyl group substituted with the C2-6 alkenyl group described above. Examples of C2 to 6 alkenylcarbonyl include vinylcarbonyl, 1-propenylcarbonyl, 2-propenylcarbonyl (allylcarbonyl), and the like.

C6 ~ 10 arylcarbonyl is a carbonyl group substituted with a C6 ~ 10 aryl group as described above. Examples of the C6-10 arylcarbonyl group include a benzyl group and a naphthylmethyl group.

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

Examples of the (C1 to 6 alkylthio) carbonyl group include (methylthio) carbonyl, (ethylthio) carbonyl, and the like.

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

In formula (II), * represents a bond.

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

In G ^a of C1 ~ 6 alkyl, C2 ~ 6 alkenyl group, C2 ~ 6 alkynyl group, C3 ~ 8 cycloalkyl group, C6 ~ 10 aryl group, a substituted the substituent group G ¹ and G ² are based, as already described.

As G ^a , a hydrogen atom or a C1-6 alkyl group (preferably an unsubstituted group) which is unsubstituted or substituted with G ^{1 is} preferred, and a hydrogen atom or a methyl group is particularly preferred.

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

C1 to 6 alkyl, C2 to 6 alkenyl, C2 to 6 alkynyl, C3 to 8 cycloalkyl, C6 to 10 aryl, 3 to 10 membered heterocyclic group, substituent G ¹ and substituents in G ^b G ² is as described.

G ^{b is} preferably a hydrogen atom or a C1-6 alkyl group (preferably unsubstituted) which is unsubstituted or substituted with G ¹ , and particularly preferably a hydrogen atom, a methyl group, or an isopropyl group.

In formula (II), T represents an oxygen atom, an oxycarbonyl group, a carbonyloxy group, an oxycarbonyloxy group, a sulfur atom, a (thio) carbonyl group, a carbonyl (thio) group, a (thio) carbonyloxy group, and an oxy group. A divalent group represented by carbonyl (thio) or -OC (= O) -N (G ^b )-.

Examples of the base represented by formula (II) include the following.

As R ⁴ , a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ -substituted C 2 to 6 alkenyl group, and an unsubstituted or G ² substituted C 6 are preferable. ~ 10 aryl C1 ~ 6 alkyl, unsubstituted or G ² substituted 3 to 10 membered heterocyclyl C1 ~ 6 alkyl, unsubstituted or G ¹ substituted C1 ~ 6 alkylcarbonyl, unsubstituted A substituted or G ² substituted C 3 to 8 cycloalkylcarbonyl group, an unsubstituted or G ¹ substituted C ¹ to 6 alkoxycarbonyl group, or a group represented by the following formula.

R ^{4 is more} preferably a hydrogen atom, an unsubstituted or G ¹ -substituted C1-6 alkylcarbonyl group (preferably unsubstituted), or an unsubstituted or G ² -substituted C3-8 cycloalkylcarbonyl group. (preferably unsubstituted), unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxycarbonyl group (preferably unsubstituted), or the following of the group represented by the formula.

R ^{4 is} particularly preferably a hydrogen atom, a methoxycarbonyl group, an ethoxycarbonyl group, an ethylfluorenyl group, an ethylcarbonyl group, a cyclopropylcarbonyl group, or a group represented by the following formula.

[A]

A in Formula (I) represents either an oxygen atom or a divalent organic group represented by Formula (III).

In formula (III), * represents a bonding position.

In the formula (III), R ⁵ and R ⁶ each independently represent a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C ¹ to 6 alkoxy group, or G ² substituted by a substituted aryloxy group of C6 ~ 10, unsubstituted or substituted with G ¹ of the alkoxycarbonyloxy, halogen, hydroxy. R ⁵ and R ⁶ may be connected to form a 3- to 6-membered ring together with the carbon atom to which R ⁵ and R ⁶ are bonded.

In the R ⁵ and R ⁶ C1 ~ ⁶ alkyl, C1 ~ 6 alkoxy group, a halogen group and a substituted group G ¹ as already described were based.

As R ⁵ , a hydrogen atom, an unsubstituted or G ¹ -substituted C1 to 6 alkyl group, an unsubstituted C1 to 6 alkoxy group, and an unsubstituted or G ² substituted C6 to 10 aryloxy group are preferred. Group, unsubstituted alkoxycarbonyloxy group, halogeno group, hydroxyl group, more preferably hydrogen atom, methyl group, methoxy group, methoxycarbonyloxy group, phenoxy group, benzyloxy group, particularly preferably hydrogen atom.

As R ⁶ , a hydrogen atom, an unsubstituted or G ¹ -substituted C1 to 6 alkyl group, an unsubstituted C1 to 6 alkoxy group, and an unsubstituted or G ² substituted C6 to 10 aryloxy group are preferred. Group, unsubstituted alkoxycarbonyloxy group, halogeno group, hydroxyl group, more preferably hydrogen atom, methyl group, methoxy group, methoxycarbonyloxy group, phenoxy group, benzyloxy group, particularly preferably hydrogen atom.

[Cy]

Cy in the formula (I) represents an unsubstituted or G ² substituted C6 to 10 aryl group, a G ³ substituted C 3 to 8 cycloalkyl group, an unsubstituted or G ² substituted 3 to 10 membered heterocyclic ring Or 13-membered heteroaryl substituted with G ² .

The C6-10 aryl group, C3-8 cycloalkyl group, 3-10 member heterocyclic group, 13 member heteroaryl group, and substituent G ^{2 in} Cy are as described above.

As the 3- to 10-membered heterocyclic group in Cy, a 3- to 6-membered heterocyclic group is preferred, and a 5- to 6-membered heterocyclic group is particularly preferred.

As Cy, G ² is preferably substituted by the C6 ~ 10 aryl group, a substituted G ² via the C5 ~ 6 cycloalkyl, substituted by the G ² 3 ~ 6-membered heterocyclic group, more preferably it is substituted by G ² C6-10 aryl (preferably phenyl), 5-6 membered heterocyclic group substituted with G ² (preferably thienyl, pyridyl or pyrimidinyl). When Cy is phenyl, the substitution position of G ² is preferably the 4-position.

As G ^{2 in} Cy, an unsubstituted or G ²¹ substituted C1-8 alkyl group, an unsubstituted or G ²¹ substituted C2-6 alkenyl group, and an unsubstituted or G ²¹ substituted C2 are preferred. ~ 6 alkynyl, hydroxy, unsubstituted or G ²¹ substituted C1 ~ 6 alkoxy, unsubstituted or G ²¹ substituted C1 ~ 6 alkylcarbonyl, unsubstituted or G ²¹ substituted C1 ~ 6 alkoxycarbonyl, unsubstituted or substituted with G ²¹ mono C1 ~ 6 alkylcarbonylamino, unsubstituted or substituted with G ²¹ N- (C1 ~ 6 alkylcarbonyl) -N- (C1 ~ 6 alkyl) amino, unsubstituted or substituted with the G ²¹ N- (C1 ~ 6 alkyl-carbonyl) -N- (C1 ~ 6 alkoxycarbonyl) amino, unsubstituted or substituted with the ²¹ G C1 ~ 6 alkoxycarbonyloxy, mercapto, unsubstituted or substituted with G ²¹ C1 ~ 6 alkylthio, unsubstituted or substituted with G ²¹ C1 ~ 6 alkylsulfinyl sulfenyl, unsubstituted or substituted of G ²² C3 ~ 8 cycloalkyl, unsubstituted or substituted with the G ²² C3 ~ 8 cycloalkenyl group, the unsubstituted or substituted by G ²² C3 ~ 8 cycloalkyl carbonyl amino carbonyl group, an the unsubstituted or substituted by G ²² C6 ~ 10 aryl group, unsubstituted or substituted with the G ²² C6 ~ 10 aryloxy, the unsubstituted or substituted by G ²² 3 ~ 10 membered Cycloalkyl group, an aryl group 13 heteroaryl, unsubstituted or substituted with the G ²² 3 to 10-membered heterocyclic group, a cyano group, a halogen group, unsubstituted or substituted with G ²¹ of C1 ~ 6 alkylene group, - The group represented by CR ^a = NR ^b is more preferably an unsubstituted or G ²¹ substituted C1-8 alkyl group, an unsubstituted or G ²¹ substituted C2-6 alkynyl group, unsubstituted or substituted with G ²¹ C1 ~ 6 alkoxy, unsubstituted or substituted with G ²¹ C1 ~ 6 alkylcarbonyl, unsubstituted or substituted with G ²² C6 ~ 10 aryl, unsubstituted or substituted with G ²² C6 ~ 10 aryloxy, 3- to 10-membered heterocyclyl, unsubstituted or substituted with G ²² , 3- to 10-membered heterocyclyl, unsubstituted or substituted with G ²² , cyano, halo, unsubstituted or substituted by group G ²¹ of C1 ~ 6 alkylene, -CR ^a = NR ^b represents the, particularly preferably unsubstituted or substituted with G ²¹ of C1 ~ 8 alkyl, unsubstituted or substituted C2 via the G ²¹ ~ 6 alkynyl, unsubstituted or G ²¹ substituted C1 ~ 6 alkoxy, unsubstituted or G ²¹ substituted C1 ~ 6 alkylcarbonyl, unsubstituted or G ²² substituted phenyl, unsubstituted Substituted or substituted G ²² phenoxy, unsubstituted or substituted G ²² 5-membered heterocyclic group (preferably 1, 2, 4- Oxazolyl, (Oxazolyl, thiazolyl, pyrazolyl, 1,2,4-triazolyl, pyridyl, pyrimidinyl), 5- to 6-membered heterocyclic oxo (preferably pyridyloxy) unsubstituted or substituted with G ²² group), a cyano group, a halogen group, unsubstituted or substituted with G alkylene of C1 ~ 6 ^21, -CR ^a = NR ^b represents the group, particularly preferably an unsubstituted or G ^{22 is} the substituted phenyl, unsubstituted or substituted with the G ²² 5 ~ 6 membered heterocyclic group (preferably 1,2,4 Oxazolyl, (Oxazolyl, thiazolyl, pyrazolyl, 1,2,4-triazolyl, pyridyl, pyrimidinyl).

The pyridine compounds of the present invention also include hydrates, various solvates, polymorphs, and the like. Furthermore, the pyridine compound of the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures and tautomers thereof. The pyridine compound of the present invention also includes its N-oxide. Here, the N-oxide is a compound in which the nitrogen atom of the pyridine ring of the formula (I) is oxidized.

[Tautomers]

When the pyridine compound of the present invention in the case of R ⁴ is the hydrogen atom, as shown below to produce the tautomer (pyridin-4-one compound). In addition, R ¹ , R ² , R ³ , A, and Cy in the formulae have the same meanings as defined in the formula (I). The pyridine compound of the present invention contains the tautomer.

[Stereoisomers]

Although the present invention is a compound represented by the same structural formula, it includes compounds with different spatial arrangements of atoms or substituents in the structure, such as all stereoisomers such as optical isomers, non-image isomers, and geometric isomers. Thing. The pyridine compound of the present invention may be a stereoisomer or a mixture of plural stereoisomers.

[Salt]

The salt of the compound (I) of the present invention is not particularly limited as long as it is a salt acceptable in agriculture and horticulture. Examples 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; salts of transition metals such as iron and copper ; Ammonia, triethylamine, tributylamine, pyridine, hydrazine and other organic base salts. The salt of the compound (I) can be obtained from the compound (I) by a known method.

[Formulation]

The agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides of the present invention are not particularly limited to dosage forms. Examples include dosage forms such as hydration agents, emulsions, powders, granules, aqueous solvents, suspensions, granule hydration agents, and lozenges. The method for preparing the preparation is not particularly limited, and a known preparation method can be adopted according to the dosage form.

Several formulation examples are shown below. In addition, the formulation formulations shown below are merely examples, and can be modified within a range that does not violate the gist of the present invention, and the present invention is not limited in any way by the following formulation examples. Unless otherwise specified, "part" means "part by weight".

(Formulation 1: Hydrating agent)

The above materials are mixed uniformly and pulverized into a fine shape to obtain a hydrating agent with an active ingredient of 40%.

(Preparation 2: Emulsion)

The above substances are mixed to obtain an emulsion with 30% of active ingredients.

(Formulation 3: powder)

The above materials are mixed uniformly and pulverized into a fine shape to obtain a powder with 10% of an active ingredient.

(Formulation 4: Granules)

The above substances were sufficiently pulverized and mixed, water was added and thoroughly kneaded, and then granulation and drying were performed to obtain granules with an active ingredient of 5%.

(Formulation 5: Suspension)

The above materials were mixed and wet-pulverized until the particle size became 3 micrometers or less, and a suspending agent with 10% of the active ingredient was obtained.

(Formulation 6: Granular Hydrating Agent)

After the above materials are mixed uniformly and pulverized into a fine shape, an appropriate amount of water is added and kneaded to make a clay shape. The clay is granulated and dried to obtain a granular hydrating agent with an active ingredient of 40%.

Next, compound examples are shown to further specifically explain the present invention. However, the present invention is not limited in any way by the following compound examples.

[Example 1]

(2,3,6-trimethyl-5-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) -4-pyridyl) methyl carbonate (compound number: 1-3) manufacturing

(Step 1) 4-benzyloxy-2,6-dimethyl-3-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) pyridine (Compound No .: 1 -13) Synthesis

554 mg of zinc was added to the dried flask, and the inside of the system was replaced with nitrogen. Add 6 ml of tetrahydrofuran and 0.04 ml of 1,2-dibromoethane, and heat to 60 ° C. After leaving to cool to room temperature, 0.02 ml of chlorotrimethylsilane was added and stirred at room temperature for 10 minutes. Under ice-cooling, a solution obtained by dissolving 1.80 g of 1- (bromomethyl) -4- (4- (trifluoromethoxy) phenoxy) benzene in 1.1 ml of tetrahydrofuran was added dropwise to the solution. . After the dropwise addition was completed, the mixture was stirred under ice-cooling for 10 minutes, and further stirred at room temperature for 2 hours to prepare a zinc reagent.

1.55 g of 4-benzyloxy-3-iodo-2,6-dimethylpyridine and 0.16 g of dichlorobis (triphenylphosphine) palladium were added to the dried flask, and the system was replaced with nitrogen. Thereafter, 10 ml of tetrahydrofuran was added thereto. The above-mentioned zinc reagent was added to this solution, and heated under reflux for 3 days. The reaction was cooled to room temperature. Thereafter, it was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.56 g of the target compound. The yield is 26%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 2.48 (s, 3H), 2.49 (s, 3H), 4.02 (s, 2H), 5.09 (s, 2H), 6.63 (s, 1H), 6.87-6.96 ( m, 4H), 7.08-7.15 (m, 4H), 7.26-7.33 (m, 5H)

(Step 2) 2,6-dimethyl-3-(((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) pyridin-4-ol (Compound No .: 1-14 Synthesis of)

0.56 g of 4-benzyloxy-2,6-dimethyl-3-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) pyridine, 10 ml of methanol, and 10 0.10 g of% palladium on carbon was mixed and stirred overnight under a hydrogen atmosphere at room temperature. The insoluble matter was removed by filtration, and the solvent was distilled off from the filtrate under reduced pressure to obtain 0.38 g of the target compound. The yield was 85%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CD ₃ OD, δ ppm) 2.28 (s, 3H), 2.30 (s, 3H), 3.90 (s, 2H), 6.25 (s, 1H), 6.89-7.00 (m, 4H), 7.19 -7.23 (m, 4H)

(Step 3) 3-iodo-2,6-dimethyl-5-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) pyridin-4-ol (Compound No. : 1-15) Synthesis

0.38 g of 2,6-dimethyl-3-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) pyridin-4-ol, 7 ml of acetic acid, and N-iodine 225 mg of succinimidine was mixed and stirred at room temperature for 2 hours. The precipitated solid was collected by filtration, and washed with a small amount of acetic acid and acetonitrile to obtain 0.18 g of the target compound. The yield was 36%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CD ₃ OD, δ ppm) 2.30 (s, 3H), 2.58 (s, 3H), 3.96 (s, 2H), 6.89-7.00 (m, 4H), 7.19-7.23 (m, 4H)

(Step 4) (3-iodo-2,6-dimethyl-5-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) 4-pyridyl) methyl carbonate Synthesis of Esters (Compound No .: 1-16)

10 ml of chloroform was added to 0.49 g of 3-iodo-2,6-dimethyl-5-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) pyridin-4-ol. And 0.19 g of triethylamine. Under ice-cooling, 0.14 g of methyl chloroformate was added dropwise to the reaction solution, and the mixture was stirred at room temperature overnight. The reaction solution was poured into saturated sodium bicarbonate water, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.48 g of the target compound. The yield was 88%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 2.49 (s, 3H), 2.77 (s, 3H), 3.84 (s, 3H), 3.97 (s, 2H), 6.90-6.97 (m, 4H), 7.07- 7.17 (m, 4H)

(Step 5) (2,3,6-trimethyl-5-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) -4-pyridyl) methyl carbonate (Compound No .: 1-3) Synthesis

0.48 g of (3-iodo-2,6-dimethyl-5-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) 4-pyridyl) methyl carbonate It was dissolved in 10 ml of 1,2-dimethoxyethane, and 60 mg of bis (di-tertiary-butyl (4-dimethylaminophenyl) phosphine) palladium dichloride, 0.24 g of potassium carbonate, and And 0.21 g of trimethyl borohydride terpolymer. The inside of the system was replaced with nitrogen and heated under reflux for 1 hour. The reaction was cooled to room temperature. Thereafter, this was poured into a saturated aqueous ammonium chloride solution, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.31 g of the target compound. The yield was 80%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 2.10 (s, 3H), 2.48 (s, 3H), 2.51 (s, 3H), 3.79 (s, 3H), 3.92 (s, 2H), 6.89-6.97 ( m, 4H), 7.08 (d, 2H), 7.15 (d, 2H)

[Example 2]

(2-isopropyl-5,6-dimethyl-3-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) -4-pyridyl) methyl carbonate (Compound No .: 1-9) Manufacturing

(Step 1) Synthesis of 4-hydroxy-2-isopropyl-5,6-dimethylnicotinic acid methyl ester

13.0 g of 3-amino-4-methyl-2-pentenoic acid methyl ester, 2,2,5,6-tetramethyl-4H-1,3-dioxetan-4-one 15.6 g, and 18.2 g of molecular sieve 4A were mixed and stirred at 170 ° C for 20 minutes. Methanol was added to this reaction liquid. Thereafter, the reaction solution was filtered, and the solvent was distilled off from the filtrate under reduced pressure. Diethyl ether was added to the obtained residue, and the precipitated crystals were collected by filtration to obtain 6.98 g of the target compound. The yield was 34%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (DMSO-d6, δ ppm) 1.20 (d, 6H), 1.80 (s, 3H), 2.26 (s, 3H), 3.70 (s, 3H), 10.57 (br.s, 1H)

(Step 2) Synthesis of 6-isopropyl-2,3-dimethylpyridin-4-ol

2.56 g of 4-hydroxy-2-isopropyl-5,6-dimethyl nicotinic acid methyl ester was dissolved in 11 ml of N-methyl-2-pyrrolidone. To this solution was added 4.86 g of lithium chloride, followed by stirring at 180 ° C for 3 hours. The reaction liquid was cooled to room temperature. Then, it poured into the saturated aqueous ammonium chloride solution, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: chloroform / methanol) to obtain 1.49 g of the target compound. The yield was 79%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CD ₃ OD, δ ppm) 1.27 (d, 6H), 1.99 (s, 3H), 2.36 (s, 3H), 2.79-2.85 (m, 1H), 6.23 (s, 1H)

(Step 3) Synthesis of 3-iodo-2-isopropyl-5,6-dimethylpyridin-4-ol

1.60 g of 6-isopropyl-2,3-dimethylpyridin-4-ol was mixed with 32 ml of chloroform, 8 ml of methanol, and 2.40 g of N-iodosuccinimide, and stirred at room temperature for 3 hours. The precipitated solid was collected by filtration, and washed with a small amount of acetonitrile and diethyl ether to obtain 1.60 g of the target compound. The yield was 57%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CD ₃ OD, δ ppm) 1.30 (d, 6H), 2.06 (s, 3H), 2.39 (s, 3H), 3.60-3.69 (m, 1H)

(Step 4) 4,4,5,5-tetramethyl-2-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) -1,3,2-di Synthesis of oxaborane

10.5 g of bis (pinacolato) diboron, 2.0 g of tetrakis (triphenylphosphine) palladium, and 14.3 g of potassium carbonate were mixed. Add 1,4-two to it 100 ml of alkane and 12.0 g of 1- (bromomethyl) -4- (4- (trifluoromethoxy) phenoxy) benzene were substituted in the system with nitrogen, and heated under reflux for 5 hours. The reaction was cooled to room temperature. Then, insoluble matter was removed by filtration, and the solvent was distilled off from the filtrate under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 5.46 g of the target compound. The yield is 40%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.23 (s, 12H), 2.28 (s, 2H), 6.88-6.98 (m, 4H), 7.13-7.18 (m, 4H)

(Step 5) 2-isopropyl-5,6-dimethyl-3-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) pyridin-4-ol ( Synthesis of compound number: 1-8)

0.30 g of 3-iodo-2-isopropyl-5,6-dimethylpyridin-4-ol, 73 mg of bis (di-tert-butyl (4-dimethylaminophenyl) phosphine) palladium dichloride And 0.43 g of potassium carbonate were mixed. Add 1,4-two to it 5ml, 4,4,5,5-tetramethyl-2-(((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) -1,3,2-dioxane 0.49 g of heteroborane and 1 ml of water were substituted in the system with nitrogen, and heated under reflux for 2 hours. The reaction was cooled to room temperature. Thereafter, it was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform / methanol) to obtain 0.08 g of the target compound. The yield was 18%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.15 (d, 6H), 2.04 (s, 3H), 2.29 (s, 3H), 3.18-3.27 (m, 1H), 3.98 (s, 2H), 6.85 6.94 (m, 4H), 7.11-7.21 (m, 4H), 7.96 (br.s, 1H)

(Step 6) (2-isopropyl-5,6-dimethyl-3-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) -4-pyridyl ) Synthesis of methyl carbonate (compound number: 1-9)

Added to 0.15 g of 2-isopropyl-5,6-dimethyl-3-((4- (4- (trifluoromethoxy) phenoxy) phenyl) methyl) pyridin-4-ol 8 ml of chloroform and 71 mg of triethylamine. 50 mg of methyl chloroformate was added dropwise to the reaction solution under ice-cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was poured into saturated sodium bicarbonate water, 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 purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.10 g of the target compound. The yield was 59%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.17 (d, 6H), 2.08 (s, 3H), 2.51 (s, 3H), 3.19-3.22 (m, 1H), 3.76 (s, 3H), 3.95 ( s, 2H), 6.89-6.94 (m, 4H), 7.06-7.15 (m, 4H)

[Example 3]

2-isopropyl-5,6-dimethyl-3- (4- (5- (trifluoromethyl) -1,2,4- Diazol-3-yl) benzyl) pyridin-4-ylmethyl carbonate

(Step 1) Synthesis of methyl 2-isopropyl-4-methoxy-5,6-dimethylnicotinate

20 g of methyl 4-hydroxy-2-isopropyl-5,6-dimethylnicotinate, 24.8 g of potassium carbonate, 25.4 g of methyl iodide, and 300 ml of acetonitrile were mixed and heated under reflux for 3 hours. The reaction solution was filtered through celite, and the solvent was distilled off under reduced pressure. The obtained residue was diluted with ethyl acetate and washed with water, and then the solvent was distilled off under reduced pressure to obtain 21.3 g of the target compound. The yield is 100%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.25 (d, 6H), 2.17 (s, 3H), 2.49 (s, 3H), 2.93 (m, 1H), 3.79 (s, 3H), 3.92 (s, 3H).

(Step 2) Synthesis of (2-isopropyl-4-methoxy-5,6-dimethylpyridin-3-yl) methanol

250 ml of tetrahydrofuran and 4.08 g of lithium aluminum hydride were mixed and cooled to -10 ° C. A solution prepared by dissolving 21.3 g of methyl 2-isopropyl-4-methoxy-5,6-dimethylnicotinate in 90 ml of tetrahydrofuran was added dropwise to the mixed solution. After completion of the dropwise addition, the temperature was raised to 30 ° C, and then cooled to 0 ° C again. This operation was repeated until the disappearance of methyl 2-isopropyl-4-methoxy-5,6-dimethylnicotinate was confirmed by thin layer chromatography. The reaction solution was cooled in an ice bath, 4.08 g of water, 4.08 g of 15% aqueous sodium hydroxide solution, and 12.2 g of water were sequentially added, and then filtered through celite, and the solvent was distilled off under reduced pressure to obtain the target Compound 17.5g. The yield was 93%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.27 (d, 6H), 1.83 (m, 1H), 2.17 (s, 3H), 2.47 (s, 3H), 3.33 (m, 1H), 3.81 (s, 3H), 4.74 (d, 2H).

(Step 3) Synthesis of 3- (bromomethyl) -2-isopropyl-4-methoxy-5,6-dimethylpyridine

15.7 g of (2-isopropyl-4-methoxy-5,6-dimethylpyridin-3-yl) methanol and 42.5 g of carbon tetrabromide were dissolved in 300 ml of dichloromethane. After 25.7 g of triphenylphosphine was added at room temperature, it was stirred at room temperature overnight. The reaction solution was washed with sodium bicarbonate water, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate), and 18.2 g of the target compound was obtained. The yield was 89%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.29 (d, 6H), 2.17 (s, 3H), 2.47 (s, 3H), 3.31 (m, 1H), 3.88 (s, 3H), 4.63 (s, 2H).

(Step 4) Synthesis of 4-((2-isopropyl-4-methoxy-5,6-dimethylpyridin-3-yl) methyl) benzonitrile

0.8 (g) of 3- (bromomethyl) -2-isopropyl-4-methoxy-5,6-dimethylpyridine, 0.647g of 4-cyanophenylboronic acid, 0.608g of potassium carbonate, 0.27 g of phenylphosphine) palladium, 10 ml of 1,2-dimethoxyethane, and 2 ml of water were mixed and replaced with argon, and then heated under reflux in an argon atmosphere for 1.5 hours. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.55 g of the target compound. The yield was 64%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.13 (d, 6H), 2.20 (s, 3H), 2.50 (s, 3H), 2.94-3.04 (m, 1H), 3.60 (s, 3H), 4.10 ( s, 2H), 7.20 (d, 2H), 7.54 (d, 2H).

(Step 5) Synthesis of N-hydroxy-4-((2-isopropyl-4-methoxy-5,6-dimethylpyridin-3-yl) methyl) benzidine

5.50 g of 4-((2-isopropyl-4-methoxy-5,6-dimethylpyridin-3-yl) methyl) benzonitrile, 100 ml of ethanol, 10 ml of water, hydroxylamine hydrochloride 2.61 g and 5.30 g of sodium carbonate were mixed and heated under reflux for 4 hours. The reaction solution was diluted with water, extracted with ethyl acetate, and the obtained organic layer was washed with water and saturated brine, and dried over magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 4.20 g of the target compound. The yield was 69%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.13 (d, 6H), 2.19 (s, 3H), 2.49 (s, 3H), 2.98-3.08 (m, 1H), 3.60 (s, 3H), 4.10 ( s, 2H), 7.10 (d, 2H), 7.50 (d, 2H).

(Step 6) 2-isopropyl-5,6-dimethyl-3- (4- (5- (trifluoromethyl) -1,2,4- Synthesis of Diazol-3-yl) benzyl) pyridin-4-ol

Dissolve 4.20 g of N-hydroxy-4-((2-isopropyl-4-methoxy-5,6-dimethylpyridin-3-yl) methyl) benzidine in 100 ml of dichloromethane, 4 ml of trifluoroacetic anhydride were mixed and stirred at room temperature for 6 hours. After the solvent was distilled off under reduced pressure, 60 ml of dimethylformamide was added to the obtained residue, and the mixture was stirred at 130 ° C for 20 minutes. To this reaction solution, 2.70 g of lithium chloride and 12.4 g of p-toluenesulfonic acid monohydrate were mixed, and stirred at 130 ° C for 15 minutes. 8.2 g of sodium bicarbonate was added to the reaction solution, and after stirring at room temperature for 5 minutes, it was diluted with water and filtered. The obtained crystals were sequentially washed with water and diethyl ether to obtain 5.20 g of the target compound. The yield was 90%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.15 (d, 6H), 2.06 (s, 3H), 2.40 (s, 3H), 3.20-3.30 (m, 1H), 4.11 (s, 2H), 7.35 ( d, 2H), 7.97 (d, 2H).

(Step 7) 2-isopropyl-5,6-dimethyl-3- (4- (5- (trifluoromethyl) -1,2,4- Synthesis of Diazol-3-yl) benzyl) pyridin-4-ylmethyl carbonate

Add 2-isopropyl-5,6-dimethyl-3- (4- (5- (trifluoromethyl) -1,2,4- 1.0 g of diazol-3-yl) benzyl) pyridin-4-ol was dissolved in 30 ml of dichloromethane, 2 ml of triethylamine and 1 ml of methyl chloroformate were mixed under cooling in an ice bath, and stirred at room temperature for 1 hour . After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 600 mg of the target compound. The yield was 52%. The results of the NMR analysis of the target compound are as follows.

¹ H-NMR (CDCl ₃ , δ ppm) 1.16 (d, 6H), 2.09 (s, 3H), 2.53 (s, 3H), 3.09-3.19 (m, 1H), 3.73 (s, 3H), 4.04 ( s, 2H), 7.23 (d, 2H), 7.99 (d, 2H).

One of the compounds produced by the same method as the above-mentioned Example is shown in Tables 1-7. The physical properties of the compounds are listed in the "physical properties" column. As the physical property data, the melting point [mp (° C)], the refractive index, or its properties are described.

In the table, Me represents methyl, Et represents ethyl, ⁿ Pr represents n-propyl, ⁱ Pr represents isopropyl, ^c Pr represents cyclopropyl, ⁿ Bu represents n-butyl, ⁱ Bu represents isobutyl, ^t Bu represents tertiary butyl, ^c Bu represents cyclobutyl, ^c Pen represents cyclopentyl, ^c Hex represents cyclohexyl, Ac represents ethenyl, Ph represents phenyl, Bn represents benzyl, Py represents pyridyl, and PINB Represents 4,4,5,5-tetramethyl-1,3,2-dioxolane.

Table 1 shows substituents in the compound represented by formula (1).

Table 2 shows substituents in the compound represented by formula (2).

Table 3 shows substituents in the compound represented by formula (3).

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

Table 5 shows the substituents in the compound represented by formula (5).

Table 6 shows substituents in the compound represented by formula (6).

Table 1 shows ¹ H-NMR data of some of the compounds described in Tables 1 to 7 above.

As described above, the compound of the present invention can be easily produced by using a known chemical reaction as in the above-mentioned examples.

[Biological test]

The following test examples show that the compound of the present invention is useful as an active ingredient of agricultural and horticultural fungicides, insecticides, or acaricides.

(Experiment example 1) Control test of wheat powdery mildew

5 parts of the compound of the present invention, 1.5 parts of polyoxyethylene sorbitan monolaurate, and 93.5 parts of dimethylformamide were mixed to prepare an emulsion of 5% as an active ingredient. The emulsion was diluted with water so that the compound of the present invention became 125 ppm to obtain a medicinal solution.

Then, the above-mentioned medicinal solution was sprayed on the wheat seedlings (variety "Chihoku", 1-2 leaf stage) cultivated in the nursery pot. After air-drying, shaking powder was inoculated with conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) and placed in a greenhouse at 20 ° C. On the 6th day after the inoculation, the appearance of disease spots on the leaves (treatment area) was investigated.

On the other hand, wheat was cultivated without spraying the diluted solution, and the appearance of disease spots (non-treated area) was similarly investigated.

The control value based on the no-treatment zone was calculated by the following formula.

Control value (%) = 100- {Area where lesions appear (treated area) / Area where lesions appear (non-treated area)) × 100

The compounds shown in Table 9 were tested for wheat powdery mildew control. The control value of any compound is above 75%.

(Experiment example 2) Control test of wheat red rust

An emulsion was prepared by the same method as in Test Example 1. The emulsion was diluted with water so that the compound of the present invention became 125 ppm to obtain a medicinal solution.

Then, the above-mentioned medicinal solution was sprayed on a wheat seedling (cultivar "Nonglin 61", 1 to 2 leaf stage) cultivated in a nursery pot. After air-drying, shake powder was inoculated with the summer spores of Puccinia recondita and placed in a greenhouse at 20 ° C. On the 12th day after the inoculation, the appearance of disease spots on the leaves (treatment area) was investigated.

On the other hand, wheat was cultivated without spraying the diluted solution, and the appearance of disease spots (non-treated area) was similarly investigated.

The control value was calculated in the same manner as in Test Example 1.

The compounds shown in Table 10 were tested for wheat rust control. The control value of any compound is above 75%.

(Test example 3) potency confirmation test against Spodoptera litura

By the same method as in Test Example 1, an emulsion with an active ingredient of 5% was prepared.

0.8 g of commercially available artificial feed (Insecta LFS, manufactured by Nippon Minko Kogyo Co., Ltd.) was thoroughly mixed with 1 μl of an emulsion, and 0.2 g of each treatment zone was filled into a plastic test container (1.4 ml in volume) to prepare a test With feed. Each treatment area was inoculated with 2 second-instar larvae of Spodoptera exigua, which were sealed with a plastic cover. It was placed in a constant temperature room at 25 ° C, and the insecticidal rate and food intake were investigated on the 5th day. The test was repeated twice. In addition, a test performed under the same conditions except that the compound of the present invention was removed from the emulsion was set as a solvent control zone. The insecticidal rate is calculated by the following formula.

Insecticidal rate (%) = (Number of dead insects / Number of test insects) × 100

The compounds shown in Table 11 were tested for efficacy against Spodoptera frugiperda. Either compound was effective against Spodoptera exigua, with an insecticidal rate of 100% or a ratio of food intake to the solvent control area of 10% or less.

(Experimental Example 4) Efficacy test against bean aphids

An emulsion was prepared by the same method as in Test Example 1. The emulsion was diluted with water so that the compound of the present invention became 125 ppm to obtain a medicinal solution.

Cowpeas were cultivated in 3-inch bowls, and the primary leaves were inoculated with bean aphid nymphs. The cowpea seedlings were sprayed with the above medicinal solution. Place cowpea seedlings in a constant temperature room at a temperature of 25 ° C and a humidity of 60%. On the 4th day after spraying, the life and death of the bean aphid were determined, and the insecticidal rate was calculated. The test was repeated twice.

The insecticidal rate was calculated in the same manner as in Test Example 3.

The compounds shown in Table 12 were tested for efficacy against the bean aphid. Each compound showed a 100% insecticidal rate against the bean aphid.

(Test Example 5) Efficacy Confirmation Test against Tetranychus kanzawa

An emulsion was prepared by the same method as in Test Example 1. The emulsion was diluted with water so that the compound of the present invention became 125 ppm to obtain a medicinal solution.

The green beans were cultivated in a 3-inch bowl, and 10 female adults of the spider mite, Kanzawa, were inoculated on the primary leaves. The medicinal solution was sprayed on the green bean sprouts. Place green bean sprouts in a constant temperature room at a temperature of 25 ° C and a humidity of 65%. On the 10th day after spraying, the life and death of the adult spider mite, Kanzawa, was determined, and the insecticidal rate was calculated. The test was repeated twice.

The insecticidal rate was calculated in the same manner as in Test Example 3.

The compounds shown in Table 13 were tested for potency against Tetranychus kanzawa. Each compound showed a 100% insecticidal rate against Tetranychus sinensis.

Those who are randomly selected from the compounds of the present invention exhibit the above-mentioned effects. Therefore, it can be understood that the compounds of the present invention have the effects of pest control, sterilization, acaricide, insecticide, etc. Compounds that cause phytotoxicity to plants and have little toxicity to humans, animals, fish, or the environment.

[Industrial availability]

The pyridine compound of the present invention is a novel compound that has the effects of pest control, sterilization, acaricide, insecticide, etc., does not cause phytotoxicity to plants, and has little toxicity to humans, animals, fish, and the environment. In particular, it shows excellent control effects on wheat diseases. The pyridine compound of the present invention is useful as an active ingredient of agricultural and horticultural fungicides, pest control agents, and insecticides or acaricides, and can be used industrially.

Claims (5)

A pyridine compound, an N-oxide compound thereof, or a tautomer or salt thereof, the pyridine compound is represented by formula (I), In formula (I), R ¹ represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or G ¹ substituted C1 ~ 6 alkoxy, unsubstituted or G ¹ substituted C1 ~ 6 alkoxycarbonyl, unsubstituted or G ¹ substituted C1 ~ 6 alkylthio group, unsubstituted or G ¹ substituted C1 ~ 6 alkylaminocarbonyl, unsubstituted or G ² substituted C6 ~ 10 aryl, cyano or halogeno group, in formula (I), R ² 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 ² of C3 ~ 8 cycloalkyl, unsubstituted or C1 ~ 6 alkoxy substituted with G ¹ , methyloxy, unsubstituted or substituted G ^1-6 alkylcarbonyloxy, unsubstituted or substituted G ^2- C 6-10 aryl, (C1-C6 alkoxyimino group, unsubstituted or substituted with G ¹ ) -C1-6 alkyl group, 3 to 10-membered heterocyclic C1- 6 alkyl group, unsubstituted or G ² substituted, cyano group or a halogen group, in the formula (I), R ³ 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 ² of C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ¹ of C1 ~ 6 alkoxy, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl-carbonyl group, an C1 ~ 6 alkoxycarbonyl, substituted with or substituted with G ¹ , carboxyl, formamyl, formyloxy, unsubstituted or substituted with G ¹ -C 6 alkylcarbonyloxy, G ² substituted C6 ~ 10 aryl, unsubstituted or G ² substituted 3 ~ 10 membered heterocyclyl, (unsubstituted or G ¹ substituted C1 ~ 6 alkoxyimino) -C1 ~ 6 alkyl, unsubstituted or G ¹ substituted mono C1 ~ 6 alkylamino, unsubstituted or G ¹ substituted C1 ~ 6 alkylamino, cyano or halogen group, formula (I) In the formula, R ⁴ represents a hydrogen atom, an unsubstituted or G ¹ substituted C1 to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or G ¹ substituted C 2 to 6 Alkynyl, unsubstituted or G ² substituted C3 ~ 8 cycloalkyl, unsubstituted or G ² substituted C6 ~ 10 aryl C1 ~ 6 alkyl, unsubstituted or G ² substituted 3 ~ 10-membered heterocyclyl C1-6 alkyl, formamyl, unsubstituted or G ¹ substituted C1-6 alkylcarbonyl, unsubstituted or G ² substituted C3-8 cycloalkylcarbonyl Group, unsubstituted or G ¹ substituted C2-6 alkenylcarbonyl, unsubstituted or G ² substituted C6-10 arylcarbonyl, unsubstituted or G ¹ substituted C1-6 alkoxycarbonyl , unsubstituted or G ¹ of C2 ~ 6 alkenyl substituted oxycarbonyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkylsulfonyl group, unsubstituted or substituted with G ¹ of C1 ~ 6 alkyl aminocarbonyl, unsubstituted or substituted with ¹ G of (C1 ~ 6 alkylthio) carbonyl group, ^a substituted or unsubstituted of C1 ~ 6 alkylamino (thiocarbonyl group) by G, or of formula (II), Organic base, In formula (II), * represents a bonding bond, and in formula (II), G ^a each independently represents a hydrogen atom, an unsubstituted or G ¹ -substituted C1 to 6 alkyl group, unsubstituted or substituted with G ¹ C2 ~ 6 alkenyl, unsubstituted or G ¹ substituted C2 ~ 6 alkynyl, unsubstituted or G ² substituted C3 ~ 8 cycloalkyl, or unsubstituted or G ² substituted C6 ~ 10 aryl group, in the formula (II), G ^b represents a hydrogen atom, an unsubstituted or G ¹ -substituted C ¹ to 6 alkyl group, an unsubstituted or G ¹ substituted C 2 to 6 alkenyl group, an unsubstituted or substituted by G ¹ group of C2 ~ 6 alkynyl, unsubstituted or substituted with G ² of C3 ~ 8 cycloalkyl, unsubstituted or substituted with G ² of the C6 ~ 10 aryl group, or unsubstituted or G ² A substituted 3 to 10-membered heterocyclic group. In the formula (II), 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), (Thio) carbonyloxy, oxycarbonyl (thio), or a divalent group represented by -OC (= O) -N (G ^b )-, in formula (I), A represents an oxygen atom or formula (III) Represents a divalent organic group, In formula (III), * represents a bonding position, and in formula (III), R ⁵ and R ⁶ each independently represent a hydrogen atom, an unsubstituted or G ¹ -substituted C1 to 6 alkyl group, an unsubstituted or G ¹ substituted C1 ~ 6 alkoxy, unsubstituted or G ² substituted C6 ~ 10 aryloxy, unsubstituted or G ¹ substituted alkoxycarbonyloxy, halo, hydroxyl, R ⁵ And R ⁶ may be connected to form a 3 to 6-membered ring together with the carbon atoms bonded by R ⁵ and R ^{6. In} the formula (I), Cy represents an unsubstituted or G ² substituted C 6 to 10 aryl group, G ² substituted C3-8 cycloalkyl, unsubstituted or G ² substituted 3-10 member heterocyclic group, or 13-membered heteroaryl group, G ¹ represents hydroxyl, C1-6 alkoxy, C1-6 Alkoxy C1 ~ 6 alkoxy, C1 ~ 6 alkoxycarbonyl, formamyloxy, C1 ~ 6 alkylcarbonyloxy, C1 ~ 6 alkoxycarbonyloxy, mono C1 ~ 6 alkoxycarbonyl Amino, cyano, amino or halogen groups, when there are two or more G ¹ substituted groups, the G ¹ may be the same as or different from each other, and G ² represents an unsubstituted or G ²¹ substituted group. C1 ~ 8 alkyl, unsubstituted or G ²¹ substituted C2-6 alkenyl, unsubstituted or G ²¹ substituted C2-6 alkynyl, hydroxyl, unsubstituted Unsubstituted or substituted by G of ²¹ C1 ~ 6 alkoxy, methyl acyl, unsubstituted or substituted with G ²¹ of C1 ~ 6 alkyl carbonyl, unsubstituted or substituted with G ²¹ of C1 ~ 6 alkoxycarbonyl Methylformyloxy, unsubstituted or G ²¹ substituted C1 ~ 6 alkylcarbonyloxy, methylamino, unsubstituted or substituted with G ²¹ mono C1 ~ 6 alkylcarbonylamino, unsubstituted substituted or unsubstituted by the G ²¹ N- (C1 ~ 6 alkyl-carbonyl) -N- (C1 ~ 6 alkyl) amino, unsubstituted or substituted with the G ²¹ N- (C1 ~ 6 alkyl-carbonyl group) -N- (C1 ~ 6alkoxycarbonyl) amino, unsubstituted or substituted with G ²¹ C1 ~ 6alkoxycarbonyloxy, unsubstituted or substituted with G ²¹ mono C1 ~ 6 alkoxy carbonyl group, unsubstituted or substituted with the G ²² C3 ~ 8 cycloalkyl, unsubstituted or substituted by the G ²² C3 ~ 8 cycloalkenyl group, unsubstituted or substituted by G ²² of C3 ~ 8 cycloalkyl Carbonylcarbonylaminocarbonyl, unsubstituted or substituted with G ²² C6 ~ 10 aryl, unsubstituted or substituted with G ²² C6 ~ 10 aryl C2 ~ 6 alkynyl, unsubstituted or substituted with G ²² C6 ~ 10 aryloxy, unsubstituted or substituted with the G ²² 3 ~ 10 membered heterocyclic group, 13 heteroaryl, unsubstituted or substituted by the G ²² 3 ~ 10 membered heteroaryl epoxy , A mercapto group, unsubstituted or substituted with G ²¹ of C1 ~ 6 alkylthio, unsubstituted or substituted by G of ²¹ C1 ~ 6 alkylsulfinyl acyl, unsubstituted or substituted with the C1 ~ 6 G ²¹ Alkylsulfonyl, pentafluorosulfanyl group, unsubstituted or substituted with G ²² C6 ~ 10 arylthio, unsubstituted or substituted with G ²² C6 ~ 10 arylsulfinyl, the unsubstituted or substituted by G ²² C6 ~ 10 aryl sulfonic acyl, unsubstituted or substituted with the single G ²² C6 ~ 10 aryl group, two hydroxyl groups boron (dihydroboryl group), a nitro group, a cyano Group, halo group, unsubstituted or substituted with G ²¹ C1-6 alkylene group, unsubstituted or substituted with G ²¹ C1-6 alkylene monooxy, unsubstituted or substituted with G ^21- substituted C1 ~ 6 alkylenedioxy, -CR ^a = NR ^b represents a group, where R ^a represents a hydrogen atom, C1 ~ 6 alkyl, unsubstituted or mono-C1 ~ substituted with G ²¹ 6 alkylcarbonylamino, or mono-C3-8 cycloalkylcarbonylamino unsubstituted or substituted with G ²² , R ^b represents unsubstituted or G ²¹ substituted C1-6 alkoxy, unsubstituted or substituted of G ²² C3 ~ 8 cycloalkoxy, unsubstituted or substituted by G ²² Phenoxy, unsubstituted or substituted with G ²¹ of the single-C1 ~ 6 alkyl group, or an unsubstituted or substituted bis G ²¹ C1 ~ 6 alkyl group, G ² substituents on the group by the presence of 2 In more than one case, the G ² may be the same as or different from each other. G ²¹ represents a C1 to 6 alkoxy group, a C1 to 6 halogenated alkoxy group, a mono C1 to 6 alkylamino group, and a di C1 to 6 alkyl group. Amine, mono (C1 ~ 6alkoxyC1 ~ 6alkylcarbonyl) amino, unsubstituted or substituted with G ²¹¹ C6 ~ 10 aryl, unsubstituted or substituted with G ²¹¹ C6 ~ 10 aryloxy group, unsubstituted or substituted with the G ²¹¹ 3 ~ 10 membered heterocyclic group, the unsubstituted or substituted by G ²¹¹ 3 ~ 10 membered heterocyclic group or a halogen group, G ²¹ substituents on the group by the presence of two In the above cases, the G ²¹ may be the same as or different from each other. G ²¹¹ represents a C1 to 6 alkyl group, a C1 to 6 halogenated alkyl group, a C1 to 6 alkoxy group, a C1 to 6 halogenated alkoxy group, or a halogen group. When there are two or more groups substituted with G ²¹¹ , the G ²¹¹ may be the same as or different from each other. G ²² represents an unsubstituted or hydroxy-substituted C1 to 6 alkyl group, C1 to 6 halogenated alkyl group, C2 ~ 6 alkenyl, C2 ~ 6 halogenated alkenyl, C2 ~ 6 alkynyl, C1 ~ 6 alkoxy, C1 ~ 6 halogenated alkoxy C1 ~ 6 alkylcarbonyl, mono C1 ~ 6 alkylamino, di C1 ~ 6 alkylamino, C1 ~ 6 alkylamino carbonyl, C1 ~ 6 alkylthio, C1 ~ 6 halogenated alkylthio, C1 ~ 6 alkylsulfinyl sulfenyl, C1 ~ 6 halogenated alkylsulfinyl sulfonyl, C1 ~ 6 alkylsulfinyl sulfonyl, C1 ~ 6 halogenated alkylsulfinyl sulfonyl, C3 ~ unsubstituted or substituted with G ²²¹ ~ 8 cycloalkyl, unsubstituted or substituted with G ²²¹ C3 ~ 8 cycloalkyl C1 ~ 6 alkyl, unsubstituted or substituted with G ²²¹ C6 ~ 10 aryl, unsubstituted or substituted with G ²²¹ 3- to 10-membered heterocyclyl, unsubstituted or substituted with G ²²¹ 3- to 10-membered heterocyclylcarbonyl, pentafluorothio, nitro, cyano, halo, pendant, unsubstituted or G ²¹¹ group of substituted C1 ~ 6 alkylene dioxy group, or represents -CR ^c = NOR ^d of, where, R ^c represents a C1 ~ 6 alkyl group, R ^d represents an unsubstituted or substituted by C3 ~ G ²²¹ of 8-cycloalkyl, when there are two or more groups substituted with G ²² , the G ²² may be the same as or different from each other, G ²²¹ represents a C1 to 6 alkyl group, a C1 to 6 halogenated alkyl group, or C1 to 6 Alkoxy, C1 ~ 6 halogenated alkoxy, mono-C1 ~ 6 alkylamino, di-C1 ~ 6 alkylamino, C6 ~ 10 aryl or halogen group, existing in the group substituted with G ²²¹ 2 In more than one case, the G ²²¹ may be the same as or different from each other.     A fungicide for agriculture and horticulture, comprising as an active ingredient at least one selected from the group consisting of a pyridine compound, an N-oxide compound, and a tautomer and a salt thereof in the first patent application.         A pest control agent comprising, as an active ingredient, at least one selected from the group consisting of a pyridine compound, an N-oxide compound thereof, and a tautomer and a salt thereof in the scope of patent application.         An insecticidal or acaricide comprising as an active ingredient at least one selected from the group consisting of a pyridine compound, an N-oxide compound thereof, and a tautomer and a salt thereof in the scope of patent application No. 1.         An external parasite controlling agent containing at least one selected from the group consisting of a pyridine compound, an N-oxide compound, and a tautomer and a salt thereof in the scope of claim 1 as an active ingredient.