WO2023276813A1

WO2023276813A1 - Pyridazinone compound, agricultural and horticultural germicide, nematicide, and medical and animal antifungal agent

Info

Publication number: WO2023276813A1
Application number: PCT/JP2022/024872
Authority: WO
Inventors: 真実岸本; 頼人 ▲桑▼原; 達弘川▲崎▼; 伸哉幸堀; 貴昭寺西; 拓真石原; 睦幸斎賀
Original assignee: 日本曹達株式会社
Priority date: 2021-06-28
Filing date: 2022-06-22
Publication date: 2023-01-05
Also published as: JPWO2023276813A1

Abstract

The present invention addresses the problem of providing a pyridazinone compound which has excellent bactericidal/antibacterial activity and excellent safety, while being industrially beneficially synthesized; and an agricultural/horticultural germicide containing the pyridazinone compound as an active ingredient.　The pyridazinone compound is a compound represented by formula (I) or a salt thereof.　In formula (I), Y represents an oxygen atom or a sulfur atom; X1 and X2 each independently represent a hydrogen atom, a halogen group, a substituted or unsubstituted C1-6 alkyl group, or the like; X3 represents a hydrogen atom, a substituted or unsubstituted linear C1-C6 alkyl group, a substituted or unsubstituted linear C2-C6 alkenyl group, or the like; X4 represents a group represented by Q-A-, a group represented by Q-A-B-, or the like; A represents a substituted or unsubstituted C1-C6 alkylene group, a substituted or unsubstituted C2-C6 alkenylene group, or the like; B represents an oxygen atom, a sulfur atom or the like; and Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted heterocyclyl group having a 5-membered to 10-membered ring.

Description

Pyridazinone compounds, agricultural and horticultural fungicides, nematicides, and medical and veterinary antifungal agents

The present invention relates to pyridazinone compounds and agricultural and horticultural fungicides. More specifically, the present invention relates to a pyridazinone compound that has excellent bactericidal and antibacterial activity, is excellent in safety, and can be industrially advantageously synthesized, and an agricultural and horticultural fungicide containing it as an active ingredient. Furthermore, it relates to a nematicide containing the above compound as an active ingredient. Furthermore, it relates to medical and veterinary antifungal agents containing the above compounds as active ingredients.

Various compounds with control activity against crop diseases have been proposed for the cultivation of agricultural and horticultural crops. In order for such compounds to be practically used as agricultural and horticultural fungicides, they must not only have sufficiently high efficacy, but also must be resistant to drug resistance, not cause chemical damage or soil contamination to plants, and must be effective against livestock and fish. Low toxicity is required.

By the way, Patent Literature 1 discloses a compound represented by the formula (A) and the like. It is disclosed that this compound has bactericidal activity, antifungal activity, and the like.

WO2021/085389A

An object of the present invention is to provide a pyridazinone compound that has excellent bactericidal and antibacterial activity, is excellent in safety, and can be industrially advantageously synthesized, and an agricultural and horticultural fungicide containing it as an active ingredient. A further object is to provide a nematicide containing the above compound as an active ingredient. A further object of the present invention is to provide medical and veterinary antifungal agents containing the aforementioned compounds as active ingredients.

As a result of intensive studies aimed at solving the above problems, the present inventors have completed the present invention including the following aspects.

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

In formula (I),
Y represents an oxygen atom or a sulfur atom;
X ¹ and X ² are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6 ~10 arylsulfonyl group, substituted or unsubstituted 5- to 6-membered heterocyclyl group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, nitro group, cyano group, represented by R ¹ -CO- a carboxy group, a group represented by R ² —O—CO—, a group represented by R ³ R ⁴ N—, a group represented by R ³ R ⁴ N—CO—, R ¹ —CO—O A group represented by -, a group represented by R ¹ -CO-NR ⁵ -, a group represented by R ² -O-CO-O-, and a group represented by R ² -O-CO-NR ⁵ - a group represented by R ³ R ⁴ N—CO—O—, a group represented by R ³ R ⁴ N—CO—NR ⁵ —, a group represented by R ² SO ₂ —NR ⁵ —, R a group represented by 3R ⁴ N--SO ₂ --, a group represented by R ¹ ^ON =CR ⁶ --, a group represented by R ³ R ⁴ NN=CR ⁶ --, or R ¹ -- representing a group represented by N═CR ⁶ —;
R ¹ is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R ² is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R ³ is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
each R ⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein R ³ and R ⁴ may together form a divalent organic group,
each R ⁵ independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R ⁶ is a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted a substituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group;
X ³ is a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R ¹ -CO A group represented by -, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4- to 6-membered heterocyclyl group, R ^N1 O- a group represented by R ^N1 --CO--O--, a group represented by R ^N1 --O--CO--O--, a group represented by R ^N1 R ^N1 N--CO--O--, and R ^N1 A group represented by -CS-O-, a group represented by R ^N1 R ^N1 N-CS-O-, a group represented by R ^N1 R ^N2 N-, a group represented by R ^N1 -CO-NR ^N2 - a group represented by R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-NR ^N2 - a group represented by R ^N1 R ^N1 N—CO—CO—NR ^N2 —, a group represented by R ^N1 —CS-NR ^N2 —, and a group represented by R ^N1 R ^N1 N—CS-NR ^N2 — a group represented by R ^N1 SO ₂ —NR ^N2 —, or a group represented by R ^N1 —C(=NR ^N1 )—NR ^N2 —,
R ^N1 and R ^N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 may together form a divalent organic group;
X ⁴ is a group represented by QA-, a group represented by QA-B-, a group represented by QB-A-, a group represented by Q-SO ₂ -NR ^N3 , a group represented by Q—C(R ⁷ )=N—, a group represented by Q—NR ^N3 —SO ₂ —, a group represented by Q—N=C(R ⁷ )—, or Q— represents a group represented by B-,
A is each independently a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or a carbonyl group;
B each independently represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR ^N3 -, where R ^N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a formyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group,
R ⁷ represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.

[2] The compound or a salt thereof according to [1], wherein X ² is a group represented by R ¹ ON=CR ⁶ -.
[3] An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] or [2] and salts thereof.
[4] The agricultural and horticultural fungicide of [3], which is for seed treatment.
[5] A nematicide containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] or [2] and salts thereof.
[6] A medical or veterinary antifungal agent containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] or [2] and salts thereof.

[7] A compound represented by formula (II) or a salt thereof.

In formula (II),
Y represents an oxygen atom or a sulfur atom;
X ¹ and X ² are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6- 10 arylsulfonyl group, substituted or unsubstituted 5- to 6-membered heterocyclyl group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, nitro group, cyano group, group represented by R ¹ -CO- , a carboxy group, a group represented by R ² —O—CO—, a group represented by R ³ R ⁴ N—, a group represented by R ³ R ⁴ N—CO—, R ¹ —CO—O— a group represented by R ¹ -CO-NR ⁵ -, a group R ² -O-CO-O-, a group R ² -O-CO-NR ⁵ - , a group represented by R ³ R ⁴ N—CO—O—, a group represented by R ³ R ⁴ N—CO—NR ⁵ —, a group represented by R ² SO ₂ —NR ⁵ —, R ³ a group represented by R ⁴ N--SO ₂ --, a group represented by R ¹ ON=CR ⁶ --, a group represented by R ³ R ⁴ N--N=CR ⁶ --, or R ¹ --N represents a group represented by =CR ⁶ -;
R ¹ is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R ² is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R ³ is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
each R ⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein R ³ and R ⁴ may together form a divalent organic group,
each R ⁵ independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R ⁶ is a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted a substituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group;
X ³ is a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R ¹ -CO A group represented by -, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4- to 6-membered heterocyclyl group, R ^N1 O- a group represented by R ^N1 --CO--O--, a group represented by R ^N1 --O--CO--O--, a group represented by R ^N1 R ^N1 N--CO--O--, and R ^N1 A group represented by -CS-O-, a group represented by R ^N1 R ^N1 N-CS-O-, a group represented by R ^N1 R ^N2 N-, a group represented by R ^N1 -CO-NR ^N2 - a group represented by R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-NR ^N2 - a group represented by R ^N1 R ^N1 N—CO—CO—NR ^N2 —, a group represented by R ^N1 —CS-NR ^N2 —, and a group represented by R ^N1 R ^N1 N—CS-NR ^N2 — a group represented by R ^N1 SO ₂ —NR ^N2 —, or a group represented by R ^N1 —C(=NR ^N1 )—NR ^N2 —,
R ^N1 and R ^N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 may together form a divalent organic group;
X ⁵ represents a group represented by HO-A-, a C1-6 alkoxycarbonyl group, or a halogeno group,
A is a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or carbonyl indicates a group.
[8] The compound or a salt thereof according to [7], wherein X ² is a group represented by R ¹ ON=CR ⁶ -.

The pyridazinone compound of the present invention is excellent in bactericidal and antibacterial activity, has a reliable effect, is excellent in safety, and can be industrially advantageously synthesized.
The agricultural and horticultural fungicide and nematicide of the present invention have an excellent control effect, do not cause phytotoxicity to plants, and are less toxic to humans, livestock and fish, and have less impact on the environment.
The medical and veterinary antifungal agents of the present invention have excellent antibacterial effects and are less toxic to humans, animals, and fish.

[Pyridazinone compound]
The pyridazinone compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I).

In the present invention, the term "unsubstituted" means only scaffolding groups. When only the name of the base group is used, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that one of the hydrogen atoms in the scaffold group is replaced with a group having the same or different structure as that of the scaffold. Thus, a "substituent" is another group attached to a scaffold group. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.

A "substituent" is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Specific examples of groups that can serve as "substituents" include the following groups.
Halogeno groups such as fluoro, chloro, bromo and iodo groups;
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group alkyl group;
vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group , 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 -C2-6 alkenyl groups such as hexenyl group and 5-hexenyl group;
ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group , 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc. C2-6 alkynyl group of;

C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group;
2-cyclopropenyl group, 2-cyclopentenyl group, C3-6 cycloalkenyl group such as 3-cyclohexenyl group;
C6-10 aryl group such as phenyl group and naphthyl group;
C6-10 aryl C1-6 alkyl groups such as benzyl group and phenethyl group;
3- to 6-membered heterocyclyl group;
3- to 6-membered heterocyclyl C1-6 alkyl group;

hydroxyl group;
C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy and t-butoxy;
C2-6 alkenyloxy groups such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group;
C2-6 alkynyloxy groups such as an ethynyloxy group and a propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
C6-10 aryl C1-6 alkoxy groups such as benzyloxy group and phenethyloxy group;

carboxy group;
formyl group;
C1-6 alkylcarbonyl groups such as acetyl group and propionyl group;
formyloxy group;
C1-6 alkylcarbonyloxy groups such as an acetyloxy group and a propionyloxy group;
Methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, C1-6 alkoxycarbonyl group such as t-butoxycarbonyl group;

C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group;
C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
C3-6 halocycloalkyl groups such as 3,3-difluorocyclobutyl groups;
C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group and 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group and trichloroacetyl group;

amino group;
C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group and diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
C6-10 aryl C1-6 alkylamino groups such as benzylamino group and phenethylamino group;

formylamino group;
C1-6 alkylcarbonylamino groups such as acetylamino group, propionylamino group, butyrylamino group, i-propylcarbonylamino group;
C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group;
unsubstituted or substituted aminocarbonyl group such as carbamoyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N-phenyl-N-methylaminocarbonyl group;
imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, (1-imino)-n-propyl group;
N-hydroxy-iminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N-methoxy-iminomethyl group, (1-(N-methoxy) -imino) substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as ethyl groups;
aminocarbonyloxy group;
C1-6 alkyl-substituted aminocarbonyloxy groups such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;

mercapto group;
C1-6 alkylthio groups such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio and t-butylthio;
C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group;
C2-6 alkenylthio groups such as a vinylthio group and an allylthio group;
C2-6 alkynylthio groups such as ethynylthio group and propargylthio group;
C1-6 alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group;
C2-6 alkenylsulfinyl groups such as allylsulfinyl groups;
C2-6 alkynylsulfinyl groups such as propargylsulfinyl groups;
C1-6 alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group;
C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group;
C2-6 alkenylsulfonyl groups such as allylsulfonyl groups;
C2-6 alkynylsulfonyl groups such as propargylsulfonyl groups;
aminothiocarbonyl group;
C1-6 alkylsulfoxyimino groups such as S,S-dimethylsulfoxyimino groups;

tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group and t-butyldimethylsilyl group;
tri-C6-10 aryl-substituted silyl groups such as triphenylsilyl groups;
cyano group;
nitro group;

A term such as "C1-6" indicates that the number of carbon atoms in the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms in substituent groups. For example, an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the base group is a butyl group and the substituent is an ethoxy group.

In addition, the above-mentioned "3- to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur atoms as ring-constituting atoms. The "3- to 6-membered heterocyclyl group" includes a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .

3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, A dioxolanyl group, a dioxanyl group and the like can be mentioned.

Five-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. can be mentioned.
A pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, etc. can be mentioned as a 6-membered heteroaryl group.
Examples of the 5-membered partially unsaturated heterocyclyl group include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, and isoxazolinyl groups.
Examples of the 6-membered partially unsaturated heterocyclyl group include a dihydropyranyl group.
Any hydrogen atom in these "substituents" may be substituted with a group having a different structure.

[Y]
Y represents an oxygen atom or a sulfur atom.
In the present invention, Y is preferably an oxygen atom.

[X ¹ and X ² ]
X ¹ and X ² are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6- 10 arylsulfonyl group, substituted or unsubstituted 5- to 6-membered heterocyclyl group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, nitro group, cyano group, group represented by R ¹ -CO- , a carboxy group, a group represented by R ² —O—CO—, a group represented by R ³ R ⁴ N—, a group represented by R ³ R ⁴ N—CO—, R ¹ —CO—O— a group represented by R ¹ -CO-NR ⁵ -, a group R ² -O-CO-O-, a group R ² -O-CO-NR ⁵ - , a group represented by R ³ R ⁴ N—CO—O—, a group represented by R ³ R ⁴ N—CO—NR ⁵ —, a group represented by R ² SO ₂ —NR ⁵ —, R ³ a group represented by R ⁴ N--SO ₂ --, a group represented by R ¹ ON=CR ⁶ --, a group represented by R ³ R ⁴ N--N=CR ⁶ --, or R ¹ --N =CR ⁶ - represents a group.

R ¹ is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
R ² is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo It represents an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
R ³ is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Each R ⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Here, R ³ and R ⁴ may together form a divalent organic group.
Each R ⁵ independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
R ⁶ is a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted It represents a substituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.

Examples of the “halogeno group” for X ¹ and X ² include a fluoro group, a chloro group, a bromo group and an iodine group.

The “C1-6 alkyl group” for X ¹ and X ² may be linear or branched. The "C1-6 alkyl group" for X ¹ includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.

The "C2-6 alkenyl group" for X ¹ and X ² includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2- propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like can be mentioned.

The "C2-6 alkynyl group" for X ¹ and X ² includes an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2- propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like can be mentioned.

The "C1-6 alkoxy group" for X ¹ and X ² includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, i -butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of the “C2-6 alkenyloxy group” for X ¹ and X ² include vinyloxy, allyloxy, propenyloxy, butenyloxy and the like.
Examples of the “C2-6 alkynyloxy group” for X ¹ and X ² include an ethynyloxy group and a propargyloxy group.

Examples of the "C1-6 alkylthio group" for X ¹ and X ² include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, and an i-propylthio group. can be done.
Examples of the “C1-6 alkylsulfinyl group” for X ¹ and X ² include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
Examples of the “C1-6 alkylsulfonyl group” for X ¹ and X ² include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.

"C1-6 alkyl group", " ^C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", " ^C2- 6 alkynyloxy group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group" or "C1-6 alkylsulfonyl group" as substituents include fluoro group, chloro group, bromo group, iodo group Halogeno groups such as; hydroxyl group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1 ~ 6 haloalkoxy group such as trifluoromethoxy group; 6 alkylideneamino)oxy group; cyclopropyl group, cyclobutyl group, cyclopentyl group, C3-6 cycloalkyl group such as cyclohexyl group; phenyl group, C6-10 aryl group such as naphthyl group; 4-methylphenyl group, 4-methoxy C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 such as phenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc. C6-10 aryl group substituted with any one or more substituents of 6 haloalkoxy groups; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl 5-membered ring heteroaryl group such as group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5-membered heteroaryl group substituted with one or more substituents; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; C1-6 alkyl group, C1-6 A 6-membered heteroaryl group substituted with one or more substituents selected from an alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a cyano group is preferred.

Examples of the “C3-6 cycloalkyl group” for X ¹ and X ² include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the “C3-6 cycloalkyloxy group” for X ¹ and X ² include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.

Examples of the “C6-10 aryl group” for X ¹ and X ² include phenyl group, naphthyl group, indanyl group, indenyl group, tetralinyl group, and the like.
Examples of the “C6-10 aryloxy group” for X ¹ and X ² include a phenoxy group and a naphthoxy group.

Examples of the “C6-10 arylthio group” for X ¹ and X ² include a phenylthio group and a naphthylthio group.
Examples of the “C6-10 arylsulfinyl group” for X ¹ and X ² include a phenylsulfinyl group and a naphthylsulfinyl group.
Examples of the “C6-10 arylsulfonyl group” for X ¹ and X ² include a phenylsulfonyl group and a naphthylsulfonyl group.

The “5- to 6-membered heterocyclyl group” for X ¹ and X ² has 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. is a group containing When there are two or more heteroatoms, they may be the same or different. Examples of the "5- to 6-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .

Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, and isoxazolinyl 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.

The “5- to 6-membered heterocyclyloxy group” for X ¹ and X ² has a structure in which a 5- to 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.

"C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group" in X ¹ and X ² , As a substituent on the "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "5- to 6-membered heterocyclyl group", or "5- to 6-membered heterocyclyloxy group", a fluoro group , chloro group, bromo group, halogeno group such as iodine group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, C1-6 alkyl groups such as n-pentyl group and n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group and 1-fluoro-n-butyl group C1-6 haloalkyl group; hydroxyl group; C1-6 alkoxy group such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group ; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1-6 haloalkoxy group such as trifluoromethoxy group; phenyl group, C6-10 aryl group such as naphthyl group; 4-methylphenyl group, C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups such as 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, or a C6-10 aryl group substituted with one or more substituents of any one of C1-6 haloalkoxy groups; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl 5-membered ring heteroaryl group such as group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group A 5-membered heteroaryl group substituted with one or more substituents; a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a 6-membered heteroaryl group such as a triazinyl group; a C1-6 alkyl group, 6-membered substituted with one or more substituents selected from a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group Ring heteroaryl groups; or cyano groups are preferred.
Furthermore, as a substituent on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "5- to 6-membered heterocyclyl group", or "5- to 6-membered heterocyclyloxy group" , oxo groups are also preferred.

In the “group represented by R ¹ —CO—” for X ¹ and X ² , R ¹ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted Alternatively, it represents an unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.

The "C1-6 alkyl group" for R ¹ includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Examples of the “C2-6 alkenyl group” for R ¹ include a vinyl group and a 1-propenyl group.
Examples of the “C2-6 alkynyl group” for R ¹ include an ethynyl group and a 1-propynyl group.
Examples of substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in R ¹ include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phenyl group, naphthyl C6-10 aryl groups such as groups; C1-6 alkyl groups such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, C6-10 aryl group substituted with one or more substituents selected from C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl 5-membered ring heteroaryl groups such as groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, tetrazolyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno 5-membered heteroaryl group substituted with one or more substituents selected from group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. 6-membered heteroaryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents 6 A membered ring heteroaryl group; or a cyano group is preferred.

Examples of the “C3-6 cycloalkyl group” for R ¹ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the “C6-10 aryl group” for R ¹ include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.

The “5- to 6-membered heterocyclyl group” for R ¹ is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- to 6-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, and isoxazolinyl 5-membered partially unsaturated heterocyclyl groups; dihydro A 6-membered partially unsaturated heterocyclyl group such as a pyranyl group can be mentioned.

Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- to 6-membered heterocyclyl group" for R ¹ include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. C1 ~ 6 alkyl group of; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, C1 ~ 6 haloalkyl group such as 1-fluoro-n-butyl group; hydroxyl group; methoxy group , ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy groups such as t-butoxy group; 2-chloro-n-propoxy group, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group and 4-chlorophenyl group , 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc., a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group C6-10 aryl group substituted with one or more substituents; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group , a 5-membered heteroaryl group such as a tetrazolyl group; substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group 5-membered heteroaryl group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered heteroaryl group such as triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 A 6-membered heteroaryl group substituted with one or more substituents selected from ∼6 haloalkyl groups or C1-6 haloalkoxy groups; or a cyano group is preferred.
Furthermore, an oxo group is also preferred as a substituent on the "C3-6 cycloalkyl group" or the "5- to 6-membered heterocyclyl group".

Specific examples of the "group represented by R ¹ -CO-" include formyl, acetyl, propionyl, butyryl, i-propylcarbonyl and the like.

In the "group represented by R -O ^- CO-" for X ¹ and X ² , R ² is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or It represents an unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Specific examples of substituents for R ² are the same as those exemplified for R ¹ .

Specific examples of the “group represented by R ² —O—CO—” include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group and the like.

In the "group represented by R ³ R ⁴ N-" for X ¹ and X ² , R ³ is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group , R ⁴ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of substituents for R ³ or R ⁴ are the same as those exemplified for R ¹ .

Here, R ³ and R ⁴ may together form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.

Specific examples of the “group represented by R ³ R ⁴ N—” include amino group, methylamino group, dimethylamino group, i-propylamino group and the like.

In the “group represented by R ³ R ⁴ N—CO—” for X ¹ and X ² , R ³ and R ⁴ have the same meanings as those in the above “group represented by R ³ R ⁴ N—” indicates
Specific examples of the “group represented by R ³ R ⁴ N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, an N-(i-propyl )—N-methylaminocarbonyl group and the like.

In the "group represented by R ¹ -CO-O-" for X ¹ and X ² , R ¹ has the same meaning as the above "group represented by R ¹ -CO-".
Specific examples of the "group represented by R ¹ -CO-O-" include an acetyloxy group and an i-propylcarbonyloxy group.

In the "group represented by R ¹ -CO-NR ⁵ -" for X ¹ and X ² , R ¹ has the same meaning as the above "group represented by R ¹ -CO-".
R ⁵ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of substituents for R ⁵ are the same as those exemplified for R ¹ .
Specific examples of the "group represented by R ¹ -CO-NR ⁵ -" include an acetylamino group and an i-propylcarbonylamino group.

In the "group represented by R -O-CO ^- O-" for X ¹ and X ² , R ² has the same meaning as in the above "group represented by R -O ^- CO-". .
Specific examples of the “group represented by R ² —O—CO—O—” include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

In the "group represented by R ² -O-CO-NR ⁵ -" for X ¹ and X ² , R ² has the same meaning as in the above "group represented by R ² -O-CO-". show. R ⁵ has the same meaning as in the above “group represented by R ¹ —CO—NR ⁵ —”.
Specific examples of the “group represented by R ² —O—CO—NR ⁵ —” include a methoxycarbonylamino group.

In the “group represented by R ³ R ⁴ N—CO—O—” for X ¹ and X ² , R ³ and R ⁴ are the same as those in the above “group represented by R ³ R ⁴ N—” indicates the meaning of
Specific examples of the “group represented by R ³ R ⁴ N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.

In the “group represented by R ³ R ⁴ N—CO—NR ⁵ —” for X ¹ and X ² , R ³ and R ⁴ are the same as those in the above “group represented by R ³ R ⁴ N—” have similar meanings. R ⁵ has the same meaning as in the above “group represented by R ¹ —CO—NR ⁵ —”.
Specific examples of the “group represented by R ³ R ⁴ N—CO—NR ⁵ —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.

In the "group represented by R ² SO ₂ -NR ⁵ -" for X ¹ and X ² , R ² has the same meaning as the above "group represented by R ² -O-CO-". R ⁵ has the same meaning as in the above “group represented by R ¹ —CO—NR ⁵ —”.
Specific examples of the “group represented by R ² SO ₂ —NR ⁵ —” include a methanesulfonylamino group and the like.

In the “group represented by R ³ R ⁴ N—SO ₂ —” for X ¹ and X ² , R ³ and R ⁴ are the same as those in the above “group represented by R ³ R ⁴ N—” indicate meaning.
Specific examples of the “group represented by R ³ R ⁴ N—SO ₂ —” include an N,N-dimethylaminosulfonyl group.

In the "group represented by R ¹ ON=CR ⁶ -" for X ¹ and X ² , R ¹ has the same meaning as the above "group represented by R ¹ -CO-".
R ⁶ is a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted It represents a substituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Specific examples of the "substituted or unsubstituted C1-6 alkyl group" or "substituted or unsubstituted 5- to 6-membered heterocyclyl group" for R ⁶ are the same as those exemplified for R ¹ . .
Examples of the “halogeno group” for R ⁶ include a fluoro group, a chloro group, a bromo group and an iodo group.
Examples of the “mono C1-6 alkylamino group” of the “substituted or unsubstituted mono C1-6 alkylamino group” for R ⁶ include a methylamino group, an ethylamino group and an i-propylamino group.
Examples of the "di-C1-6 alkylamino group" of the "substituted or unsubstituted di-C1-6 alkylamino group" for R ⁶ include a dimethylamino group, a diethylamino group, an N-methyl-Ni-propylamino group, and the like. can be mentioned.
The "C1-6 alkoxy group" of the "substituted or unsubstituted C1-6 alkoxy group" for R ⁶ includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, n- A hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group and the like can be mentioned.
The "C1-6 alkylthio group" of the "substituted or unsubstituted C1-6 alkylthio group" for R ⁶ includes methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio groups, i-propylthio groups, and the like.
Substituents on the "C1-6 alkoxy group", "mono-C1-6 alkylamino group", "di ^- C1-6 alkylamino group" or "C1-6 alkylthio group" for R ⁶ include " The same substituents as exemplified as substituents on "C1-6 alkyl group" can be mentioned.
Specific examples of the “group represented by R ¹ ON=CR ⁶ —” include a 1-(i-propoxyimino)ethyl group.

In the "group represented by R ³ R ⁴ NN=CR ⁶ -" for X ¹ and X ² , R ³ and R ⁴ are the same as those in the above "group represented by R ³ R ⁴ N-". have similar meanings. R ⁶ has the same meaning as in the above “group represented by R ¹ ON=CR ⁶ —”.

In the "group represented by R ¹ -N=CR ⁶ -" for X ¹ and X ² , R ¹ and R ⁶ are the same as in the above "group represented by R ¹ ON=CR ⁶ -" indicates the meaning of

In the present invention, X ¹ is preferably a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Preferred examples of X ² include "a group represented by R ¹ ON=CR ⁶ -".

[ ^X3 ]
X ³ is a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R ¹ -CO A group represented by -, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4- to 6-membered heterocyclyl group.

Examples of the “linear C1-6 alkyl group” for X ³ include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group.
The "linear C2-6 alkenyl group" for X ³ includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2- Pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group and 5-hexenyl group can be mentioned.
The "straight-chain C2-6 alkynyl group" for X ³ includes an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2- Pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group and the like can be mentioned.
Examples of the “4-membered heterocyclyl group” for X ³ include an azetidinyl group and an oxetanyl group.
Specific examples of other substituents for X ³ are the same as those exemplified for X ¹ and X ² .

In the present invention, preferred X ³ is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted C6-10 aryl group. can.
In the present invention, more preferred X ³ is a substituted linear C1-6 alkyl group.

Substituents on Linear C1-6 Alkyl Groups, Substituents on Linear C2-6 Alkenyl Groups, Substituents on Linear C2-6 Alkynyl Groups, Substituents on C3-6 Cycloalkyl Groups, C6-10 Examples of substituents on the aryl group or substituents on the 4- to 6-membered heterocyclyl group include one or more substituents selected from the following group of substituents (hereinafter, this substituent is sometimes represented by the symbol "G").
Moreover, when there are two or more substituents (G), two of them may combine to form a divalent organic group. Substituent groups are shown below.
halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1 ~ 6 alkylsulfonyl group, substituted or unsubstituted C3 ~ 6 cycloalkyl group, substituted or unsubstituted C3 ~ 6 cycloalkyloxy group, substituted or unsubstituted C6 ~ 10 aryl group, substituted or unsubstituted C6 ~10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3-10 membered ring heterocyclyl group, substituted or unsubstituted 3- to 10-membered heterocyclyloxy group, nitro group, cyano group, group represented by R ^a —CO—, carboxy group, R ^b —O—CO— a group represented by R ^c R ^d N—, a group represented by R ^c R ^d N—CO—, a group represented by R ^c R ^d N—NR ^d —CO—, R ^b SO ₂ a group represented by -NR ^d -CO-, a group represented by R ^a -CO-O-, a group represented by R ^a -CO-NR ^e -, a group represented by R ^a -CO-CO-NR ^e - a group represented by R ^a -CO-NR ^e -NR ^e -, a group represented by R ^a -CO-NR ^e -NR ^e -CO-, R ^b -O-CO-O- A group represented by R ^b —O—CO—NR ^e — A group represented by R ^c R ^d N—CO—O— R ^c R ^d N—CO—NR ^e — A group represented by R ^c R ^d N—CO—CO—NR ^e — A group represented by R ^a —CS-NR ^e — R ^c R ^d N—CS-NR ^e — a group represented by R ^b SO ₂ —NR ^e —, a group represented by R ^c R ^d N—SO ₂ —, a group represented by R ^a ON=CR ^f —, R ^h R ^j A group represented by C=NO-, a group represented by R ^a -C(=NR ^g )-NR ^e -, a group represented by R ^c R ^d NC(=NR ^g )- a group represented by R ^h R ⁱ S(=O)=N--CO--, a group represented by R ^h R ⁱ S=N--CO--.

In the above substituent groups, each R ^a is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 10-membered heterocyclyl group.
R ^b each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo It represents an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Each R ^c is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
R ^d each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group, R ^c and R ^d may together form a divalent organic group.
Each R ^e independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group.
R ^f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
Each R ^g independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Each R ^h independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group.
Each R ⁱ independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group, wherein R ^h and R ⁱ together form a divalent An organic group may be formed.

Examples of the "halogeno group" in G include a fluoro group, a chloro group, a bromo group, and an iodo group.

The “C1-6 alkyl group” for G may be linear or branched.
The "C1-6 alkyl group" in G includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s- Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.

The "C2-6 alkenyl group" in G includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group , 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.

The "C2-6 alkynyl group" in G includes an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group , 1,1-dimethyl-2-butynyl group, and the like.

The "C1-6 alkoxy group" for G includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, Examples include s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of the "C2-6 alkenyloxy group" for G include a vinyloxy group, an allyloxy group, a propenyloxy group and a butenyloxy group.
Examples of the "C2-6 alkynyloxy group" for G include an ethynyloxy group and a propargyloxy group.

Examples of the "C1-6 alkylthio group" for G include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group and an i-propylthio group.
Examples of the "C1-6 alkylsulfinyl group" for G include a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group.
Examples of the "C1-6 alkylsulfonyl group" for G include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.

"C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkynyloxy group" in G ”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” or “C1-6 alkylsulfonyl group” include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group. hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C1-6 alkylthio groups such as methylthio group and ethylthio group; C1- such as methylsulfinyl group and ethylsulfinyl group C1-6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; C6 such as phenyl group and naphthyl group ~10 aryl group; C1-6 alkyl group, C1-6 alkoxy such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group C6-10 aryl group substituted with one or more substituents selected from group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group , oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, 5-membered heteroaryl group such as tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 5-membered heteroaryl group substituted with one or more substituents selected from 6 haloalkyl groups or C1-6 haloalkoxy groups; 6-membered rings such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group 6-membered heteroaryl group substituted with any one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group Aryl groups; or cyano groups are preferred.

Examples of the "C3-6 cycloalkyl group" for G include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the "C3-6 cycloalkyloxy group" for G include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.

Examples of the "C6-10 aryl group" for G include a phenyl group and a naphthyl group.
Examples of the "C6-10 aryloxy group" for G include a phenoxy group and a naphthoxy group.

Examples of the "C6-10 arylthio group" for G include a phenylthio group and a naphthylthio group.
Examples of the "C6-10 arylsulfinyl group" for G include a phenylsulfinyl group and a naphthylsulfinyl group.
Examples of the "C6-10 arylsulfonyl group" for G include a phenylsulfonyl group and a naphthylsulfonyl group.

The "3- to 10-membered heterocyclyl group" for G is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic.
Examples of the "3- to 10-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .

3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, A dioxolanyl group, a dioxanyl group and the like can be mentioned.
Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc. 10-membered heteroaryl group;
Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl; 9-membered partially unsaturated such as indolinyl, isoindolinyl, 2,3-dihydrobenzofuranyl and 1,3-dihydrobenzofuranyl heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;

The "3- to 10-membered heterocyclyloxy group" in G has a structure in which a 3- to 10-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.

"C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10" in G Arylsulfinyl group", "C6-10 arylsulfonyl group", "3- to 10-membered heterocyclyl group" or "3- to 10-membered heterocyclyloxy group" include a fluoro group, a chloro group, halogeno groups such as bromo group and iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group , C1-6 alkyl groups such as n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro - n-propoxy group, 2,3-dichlorobutoxy group, C1 ~ 6 haloalkoxy group such as trifluoromethoxy group; C3 ~ 6 cycloalkyl C1 ~ 6 alkoxy group; C6 ~ 10 aryl C1 ~ 6 alkoxy group; (C1 ~6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents C6-10 aryl)C1-6 alkoxy group; 5-membered heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group with one or more substituents substituted 5-membered heteroaryl) C1-6 alkoxy group; 6-membered heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or 6-membered ring heteroaryl substituted with one or more substituents of any C1-6 haloalkoxy group) C1-6 alkoxy group; methylthio group, C1-6 alkylthio group such as ethylthio group: methylsulfinyl group, ethyl C1-6 alkylsulfinyl group such as sulfinyl group; C1-6 alkylsulfonyl group such as methylsulfonyl group and ethylsulfonyl group; C such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group 1-6 haloalkylthio group: C1-6 haloalkylsulfinyl group such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group C1-6 haloalkylsulfonyl group such as; C3-6 cycloalkyl group such as cyclopropyl group and cyclobutyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy a C3-6 cycloalkyl group substituted with one or more substituents, or a cyano group; a C3-6 cycloalkenyl group; a phenyl group, a C6-10 aryl group such as a naphthyl group; a 4-methylphenyl group, C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups such as 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, or a C6-10 aryl group substituted with any one or more substituents of a C1-6 haloalkoxy group; an aziridinyl group, an epoxy group, an azetidinyl group, a 3- to 4-membered saturated heterocyclyl group such as an oxetanyl group; 3- to 4-membered saturated heterocyclyl group substituted with one or more substituents selected from a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; pyrrolidinyl group , tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, 5- to 6-membered saturated heterocyclyl group such as dioxanyl group; C1-6 alkyl group, C1-6 5- to 6-membered saturated heterocyclyl group substituted with one or more substituents selected from an alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a pyrrolyl group, a furyl group, a thienyl group, 5-membered ring heteroaryl groups such as imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, 5-membered heteroaryl group substituted with one or more substituents selected from a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; 6-membered heteroaryl group such as dazinyl group and triazinyl group; substitution of any one or more of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 6-membered heteroaryl group substituted with a group; pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, 5-membered partially unsaturated heterocyclyl group such as isoxazolinyl group; 5-membered ring partially saturated heterocyclyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; dihydropyranyl 6-membered ring partially unsaturated heterocyclyl group such as group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group with one or more substituents a substituted 6-membered partially saturated heterocyclyl group;
a group represented by R ^G1 —CO— (wherein R ^G1 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, C1-6 alkyl group substituted with one or more substituents of a phenyl group or a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a haloalkyl group or a C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from ∼6 haloalkyl group or C1-6 haloalkoxy group)C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or a C3-6 cycloalkyl group substituted with one or more substituents of a cyano group; a C6-10 aryl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or C6-10 aryl group substituted with one or more substituents of any one of C1-6 haloalkoxy groups; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, a 5- to 6-membered heteroaryl group substituted with one or more substituents; The same applies to R ^G1 below.);
carboxy group;
A group represented by R ^G2 —O—CO— (wherein R ^G2 is a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl or a C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl C6-10 aryl)C1-6 alkyl group substituted with one or more substituents, or C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from a 6-haloalkyl group or a C1-6 haloalkoxy group) C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl group C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or C3-6 cycloalkyl group substituted with cyano group; C6-10 aryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group a C6-10 aryl group substituted with one or more substituents; a 5- to 6-membered heteroaryl group; or; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1 A 5- to 6-membered heteroaryl group substituted with one or more substituents selected from any one of up to 6 haloalkoxy groups; The same applies to R ^G2 below.);
A group represented by R ^G1 R ^G1 N- (R ^G1 in the formula may be the same or different. R ^G1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.);
A group represented by R ^G1 R ^G1 N—CO— (R ^G1 in the formula may be the same or different. R ^G1 together may be a trimethylene group, tetramethylene group, pentamethylene group, or A methyleneoxydimethylene group may be formed.);
a group represented by R ^G1 -CO-O-; a group represented by R ^G1 -CO-NR ^G3 - (wherein R ^G3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; The same applies to R ^G3 below.);
A group represented by R ^G2 -O-CO-O-; a group represented by R ^G2 -O-CO-NR ^G3 -; a group represented by R ^G1 R ^G1 N-CO-O- (in the formula R ^G1 may be the same or different, and R ^G1 may together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
A group represented by R ^G1 R ^G1 N—CO—NR ^G3 — (in the formula, R ^G1 may be the same or different; R ^G1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, , or may form a dimethyleneoxydimethylene group); a group represented by R ^G2 SO ₂ —NR ^G3 —; a group represented by R ^G1 R ^G1 N—SO ₂ — (in the formula, R ^G1 may be the same or different, and R ^G1 together may form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
a group represented by R ^G1 -ON=C(R ^G4 )- (wherein R ^G4 represents a hydrogen atom or a C1-6 alkyl group); (R ^G1 ) ₂ C=N-O- A group represented by (R ^{1 G1} in the formula may be the same or different. ^RG1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.);
A pentafluorosulfanyl group, a nitro group, or a cyano group are preferred.
Furthermore, as a substituent on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "3- to 10-membered heterocyclyl group", or "3- to 10-membered heterocyclyloxy group" , oxo groups are also preferred.

In the "group represented by R ^a -CO-" for G, R ^a is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted It represents a C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 10-membered heterocyclyl group.

The "C1-6 alkyl group" for R ^a includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Examples of the “C2-6 alkenyl group” for R ^a include a vinyl group and a 1-propenyl group.
Examples of the “C2-6 alkynyl group” for R ^a include an ethynyl group and a 1-propynyl group.
Examples of substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in R ^a include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C1-6 alkylthio groups such as methylthio group and ethylthio group; C1-6 groups such as methylsulfinyl group and ethylsulfinyl group alkylsulfinyl group; methylsulfonyl group, C1-6 alkylsulfonyl group such as ethylsulfonyl group; carboxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t -C1 ~ 6 alkoxycarbonyl group such as butoxycarbonyl group; C3 ~ 6 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; C6 ~ 10 aryl group such as phenyl group and naphthyl group; 4-methyl phenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc., C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl group substituted with one or more substituents selected from haloalkyl group or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl 5-membered ring heteroaryl group such as group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 5-membered heteroaryl group substituted with any one or more substituents of haloalkoxy group; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; C1-6 a 6-membered heteroaryl group substituted with one or more substituents selected from an alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or cyano groups are preferred.

Examples of the “C3-6 cycloalkyl group” for R ^a include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the “C6-10 aryl group” for R ^a include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.

The “3- to 10-membered heterocyclyl group” for R ^a is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic.
Examples of the "3- to 10-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .
3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, Dioxolanyl group, dioxanyl group and the like can be mentioned.
Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc. 10-membered heteroaryl group;
Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl group; 9-membered partially unsaturated ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;

Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "3- to 10-membered heterocyclyl group" for R ^a include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. C1 ~ 6 alkyl group of; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, C1 ~ 6 haloalkyl group such as 1-fluoro-n-butyl group; hydroxyl group; methoxy group , ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy groups such as t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1-6 haloalkoxy group such as trifluoromethoxy group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10 aryl C1-6 alkoxy group; (C1-6 alkyl group, C1 ~6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents C6-10 aryl)C1-6 alkoxy group; 5-membered ring heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5-membered ring substituted with one or more substituents heteroaryl) C1-6 alkoxy group; 6-membered heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy 6-membered ring heteroaryl substituted with one or more substituents) C1-6 alkoxy group; C1-6 alkylthio group such as methylthio group and ethylthio group; C1- such as methylsulfinyl group and ethylsulfinyl group 6 alkylsulfinyl group; methylsulfonyl group, C1-6 alkylsulfonyl group such as ethylsulfonyl group; trifluoromethylthio group, C1-6 haloalkylthio group such as 2,2,2-trifluoroethylthio group: trifluoromethylsulfinyl a C1-6 haloalkylsulfinyl group such as a 2,2,2-trifluoroethylsulfinyl group; a trifluoromethylsulfonyl group; a 2,2,2-trifluoroethyls C1-6 haloalkylsulfonyl group such as sulphonyl group; C3-6 cycloalkyl group such as cyclopropyl group, cyclobutyl group and cyclopentyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a C3-6 cycloalkyl group substituted with one or more substituents of a cyano group; a C3-6 cycloalkenyl group; a phenyl group, a C6-10 aryl group such as a naphthyl group; -C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 such as methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group C6-10 aryl group substituted with one or more substituents selected from ∼6 haloalkyl groups or C1-6 haloalkoxy groups; saturated 3- to 4-membered rings such as aziridinyl groups, epoxy groups, azetidinyl groups and oxetanyl groups; Heterocyclyl group; saturated 3- to 4-membered ring substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group heterocyclyl group; pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and other 5- to 6-membered saturated heterocyclyl groups; C1-6 alkyl a 5- to 6-membered saturated heterocyclyl group substituted with one or more substituents selected from a group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; pyrrolyl group, furyl five-membered ring heteroaryl groups such as groups, thienyl groups, imidazolyl groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, tetrazolyl groups; C1-6 alkyl groups, C1 ~6 alkoxy group, halogeno group, C1-6 haloalkyl group, or 5-membered heteroaryl group substituted with one or more substituents of C1-6 haloalkoxy group; pyridyl group, pyrazinyl group, pyrimidinyl group, 6-membered heteroaryl group such as pyridazinyl group and triazinyl group; substitution of one or more of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group at base Substituted 6-membered heteroaryl group; 5-membered partially unsaturated heterocyclyl group such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group; C1-6 alkyl a 5-membered ring partially saturated heterocyclyl group substituted with one or more substituents selected from a group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a dihydropyranyl group, etc. 6-membered partially unsaturated heterocyclyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents a six-membered ring partially saturated heterocyclyl group;
A group represented by R ^q1 —CO— (wherein R ^q1 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, C1-6 alkyl group substituted with one or more substituents of a phenyl group or a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a haloalkyl group or a C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from ∼6 haloalkyl group or C1-6 haloalkoxy group)C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or a C3-6 cycloalkyl group substituted with one or more substituents of a cyano group; a C6-10 aryl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or C6-10 aryl group substituted with one or more substituents of any one of C1-6 haloalkoxy groups; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a 5- to 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 haloalkyl group or a C1-6 haloalkoxy group; The same applies to R ^q1 below.);
carboxy group;
A group represented by R ^q2 —O—CO— (wherein R ^q2 is a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl or a C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl C6-10 aryl)C1-6 alkyl group substituted with one or more substituents, or C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from a 6-haloalkyl group or a C1-6 haloalkoxy group) C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl group C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or C3-6 cycloalkyl group substituted with any one or more substituents of cyano group; C6-10 aryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1 C6-10 aryl group substituted with any one or more substituents of ~6 haloalkoxy group; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, a 5- to 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 haloalkyl group or a C1-6 haloalkoxy group; the same applies to R ^q2 below.);
A group represented by R ^q1 R ^q1 N- (R ^q1 in the formula may be the same or different. R ^q1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.);
A group represented by R ^q1 R ^q1 N—CO— (R ^q1 in the formula may be the same or different. Together, R ^q1 may be a trimethylene group, a tetramethylene group, a A methyleneoxydimethylene group may be formed.);
a group represented by R ^q1 —CO—O—; a group represented by R ^q1 —CO—NR ^q3 — (wherein R ^q3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; The same applies to R ^q3 below.);
A group represented by R ^q2 —O—CO—O—; a group represented by R ^q2 —O—CO—NR ^q3 —; a group represented by R ^q1 R ^q1 N—CO—O— (in the formula R ^q1 may be the same or different, and R ^q1 may be combined to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.);
A group represented by R ^q1 R ^q1 N—CO—NR ^q3 — (in the formula, R ^q1 may be the same or different. R ^q1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, , or may form a dimethyleneoxydimethylene group); a group represented by R ^q2 SO ₂ —NR ^q3 —; a group represented by R ^q1 R ^q1 N—SO ₂ — (in the formula, R ^q1 may be the same or different, and R ^q1 may be combined to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.);
a group represented by R ^q1 -ON=C(R ^q4 )- (wherein R ^q4 represents a hydrogen atom or a C1-6 alkyl group); (R ^q1 ) ₂ C=N-O- (R ^q1 in the formula may be the same or different. R ^q1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.);
A pentafluorosulfanyl group, a nitro group, or a cyano group are preferred.
Furthermore, an oxo group is also preferred as a substituent on the "C3-6 cycloalkyl group" or the "3- to 10-membered heterocyclyl group".

Specific examples of the "group represented by R ^a -CO-" include a formyl group, an acetyl group, an i-propylcarbonyl group and the like.

In the "group represented by R ^b -O-CO-" for G, R ^b is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ~6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Specific examples of the substituent for R ^b are the same as those exemplified for R ^a .

Specific examples of the "group represented by R ^b -O-CO-" include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group and a t-butoxycarbonyl group. and the like.

In the "group represented by R ^c R ^d N-" for G, R ^c is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted A C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and R ^d is , a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of substituents for R ^c or R ^d are the same as those exemplified for R ^a .
The "C1-6 alkoxy group" in R ^d includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, and an i-butoxy group. , s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of substituents on the "C1-6 alkoxy group" in R ^d include halogeno groups such as fluoro, chloro, bromo and iodo groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group , n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, etc. C1 ~ 6 haloalkoxy group of; cyclopropyl group, cyclobutyl group, cyclopentyl group, C3 ~ 6 cycloalkyl group such as cyclohexyl group; phenyl group, C6 ~ 10 aryl group such as naphthyl group; 4-methylphenyl group, 4- C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1 such as methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group A C6-10 aryl group substituted with any one or more substituents of up to 6 haloalkoxy groups; or a cyano group is preferred.

Here, R ^c and R ^d may together form a divalent organic group.
Examples of divalent organic groups that can be formed include a substituted or unsubstituted C2-5 alkylene group, a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group, a substituted or unsubstituted C1-3 alkylenethio C1-3 Examples include an alkylene group, or a substituted or unsubstituted C1-3 alkyleneimino C1-3 alkylene group.
Additionally, mention may be made of silicon-containing divalent hydrocarbon groups such as -CH ₂ CH ₂ -Si(CH ₃ ) ₂ -CH ₂ CH ₂ -.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of the "C1-3 alkylenethio C1-3 alkylene group" include a dimethylenethiodimethylene group and the like.
Examples of the "C1-3 alkyleneimino C1-3 alkylene group" include a dimethyleneiminodimethylene group and the like.
Here, the imino group of "C1-3 alkylenealkyleneimino C1-3 alkylene group" means -NH-.
Substituents on "C2-5 alkylene group", "C1-3 alkyleneoxy C1-3 alkylene group", "C1-3 alkylenethio C1-3 alkylene group" and "C1-3 alkyleneimino C1-3 alkylene group" Examples include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodine group; C1-6 alkyl group such as t-butyl group; methylidene group; or C1 such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group ~6 haloalkyl groups are preferred.

Specific examples of the “group represented by R ^c R ^d N—” include amino group, methylamino group, dimethylamino group, i-propylamino group and the like.

In the “group represented by R ^c R ^d N—CO—” for G, R ^c and R ^d have the same meanings as those in the above “group represented by R ^c R ^d N—”.
Specific examples of the “group represented by R ^c R ^d N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, an N-(i-propyl )—N-methylaminocarbonyl group and the like.

In the “group represented by R ^c R ^d N—NR ^d —CO—” for G, R ^c and R ^d have the same meanings as those in the above “group represented by R ^c R ^d N—” show.
Specific examples of the “group represented by R ^c R ^d N—NR ^d —CO—” include a 2,2-dimethylhydrazine-1-carbonyl group.

In the "group represented by R ^b SO ₂ -NR ^d -CO-" for G, R ^b has the same meaning as in the above "group represented by R ^b -O-CO-", and R ^d has the same meaning as in the above “group represented by R ^c R ^d N—”.
Specific examples of the "group represented by R ^b SO ₂ -NR ^d -CO-" include a (methylsulfonyl)carbamoyl group, a (cyclopropylsulfonyl)carbamoyl group, and a ((1-methylcyclopropyl)sulfonyl)carbamoyl group. etc. can be mentioned.

In the "group represented by R ^a -CO-O-" for G, R ^a has the same meaning as in the above "group represented by R ^a -CO-".
Specific examples of the "group represented by R ^a -CO-O-" include an acetyloxy group.

In the "group represented by R ^a -CO-NR ^e -" for G, R ^a has the same meaning as in the above "group represented by R ^a -CO-".
R ^e represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent for R ^e are the same as those exemplified for R ^a .
Specific examples of the "group represented by R ^a -CO-NR ^e -" include an acetylamino group, a propionylamino group, a butyrylamino group, an i-propylcarbonylamino group and the like.

In the "group represented by R ^a -CO-CO-NR ^e -" for G, R ^a has the same meaning as in the above "group represented by R ^a -CO-". R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Specific examples of the “group represented by R ^a —CO—CO—NR ^e —” include an oxopropanamide group.

In the "group represented by R ^a -CO-NR ^e -NR ^e -" for G, R ^a has the same meaning as in the above "group represented by R ^a -CO-". R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Specific examples of the “group represented by R ^a —CO—NR ^e —NR ^e —” include an acetylhydrazinyl group and an i-propylcarbonylhydrazinyl group.

In the "group represented by R ^a -CO-NR ^e -NR ^e -CO-" for G, R ^a has the same meaning as in the above "group represented by R ^a -CO-". R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Specific examples of the "group represented by R ^a -CO-NR ^e -NR ^e -CO-" include 2-acetylhydrazine-1-carbonyl group.

In the “group represented by R ^b —O—CO—O—” for G, R ^b has the same meaning as in the above “group represented by R ^b —O—CO—”.
Specific examples of the “group represented by R ^b —O—CO—O—” include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

In the “group represented by R ^b —O—CO—NR ^e —” for G, R ^b has the same meaning as in the above “group represented by R ^b —O—CO—”. R ^e has the same meaning as in the above “group represented by R ^b —CO—NR ^e —”.
Specific examples of the “group represented by R ^b —O—CO—NR ^e —” include a methoxycarbonylamino group.

In the “group represented by R ^c R ^d N—CO—O—” for G, R ^c and R ^d have the same meanings as those in the above “group represented by R ^c R ^d N—” .
Specific examples of the “group represented by R ^c R ^d N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.

In the “group represented by R ^c R ^d N—CO—NR ^e —” for G, R ^c and R ^d have the same meanings as those in the above “group represented by R ^c R ^d N—” show. R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Specific examples of the “group represented by R ^c R ^d N—CO—NR ^e —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.

In the “group represented by R ^c R ^d N—CO—CO—NR ^e —” for G, R ^c and R ^d are the same as those in the above “group represented by R ^c R ^d N—” indicate meaning. R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Specific examples of the "group represented by R ^c R ^d N-CO-CO-NR ^e -" include 2-(methylamino)-2-oxoacetamide group, 2-(t-butylamino)-2- An oxoacetamide group and the like can be mentioned.

In the "group represented by R ^a -CS-NR ^e -" for G, R ^a has the same meaning as in the above "group represented by R ^a -CO-". R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Specific examples of the "group represented by R ^a -CS-NR ^e -" include an ethanethioamide group, a propanethioamide group, a 2-methylpropanethioamide group and the like.

In the “group represented by R ^c R ^d N—CS—NR ^e —” for G, R ^c and R ^d have the same meanings as those in the above “group represented by R ^c R ^d N—” show. R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Specific examples of the “group represented by R ^c R ^d N—CS—NR ^e —” include a 3,3-dimethylthioureido group.

In the “group represented by R ^b SO ₂ —NR ^e —” for G, R ^b has the same meaning as in the above “group represented by R ^b —O—CO—”. R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Specific examples of the “group represented by R ^b SO ₂ —NR ^e —” include a methanesulfonylamino group.

In the “group represented by R ^c R ^d N—SO ₂ —” for G, R ^c and R ^d have the same meanings as those in the above “group represented by R ^c R ^d N—”.
Specific examples of the “group represented by R ^c R ^d N—SO ₂ —” include an N,N-dimethylaminosulfonyl group.

In the "group represented by R ^a ON=CR ^f -" for G, R ^a has the same meaning as in the above "group represented by R ^a -CO-".
R ^f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent for R ^f are the same as those exemplified for ^Ra .
Specific examples of the "group represented by R ^a ON=CR ^f -" include (hydroxyimino)methyl group and (ethoxyimino)methyl group.

In the "group represented by R ^a -C(=NR ^g )-NR ^e -" for G, R ^a has the same meaning as in the above "group represented by R ^a -CO-". R ^e has the same meaning as in the above “group represented by R ^a —CO—NR ^e —”.
Each R ^g independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent for ^Rg are the same as those exemplified for ^Ra .

In the "group represented by R ^c R ^d NC(=NR ^g )-" for G, R ^c and R ^d are the same as those in the above "group represented by R ^c R ^d N-" indicate meaning. R ^g has the same meaning as in the above "group represented by R ^a -C(=NR ^g )-NR ^e -".

In the "group represented by R ^h R ⁱ S(=O)=N-CO-" for G, each R ^h is independently a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted represents a C6-10 aryl group, and each R ⁱ independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group;
Specific examples of substituents for R ^h or R ⁱ are the same as those exemplified for R ^a .

Here, R ^h and R ⁱ may together form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.

In the "group represented by R ^h R ⁱ S=N--CO-" in G, R ^h or R ⁱ is the above "group represented by R ^h R ⁱ S(=O)=N--CO--" have similar meanings to those in

In the "group represented by R ^h R ^j C=NO-" for G, R ^h and R ^j are the same as in the above "group represented by R ^h R ^j S=NO-" indicate meaning.
Specific examples of the “group represented by R ^h R ^j C═N—O—” include (propan-2-ylideneamino)oxy group and the like.

When there are two or more substituents (G), the divalent organic groups that can be formed by two of them together include a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxy C1-4 An alkylene group, a substituted or unsubstituted oxy C2-3 alkyleneoxy group, or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group can be mentioned.
Examples of the "C1-5 alkylene group" include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
Examples of the "oxy C1-4 alkylene group" include an oxymethylene group and an oxydimethylene group.
Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethylenoxy group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on the "C1-5 alkylene group", "oxy-C1-4 alkylene group", "oxy-C2-3 alkyleneoxy group" and "C1-3 alkyleneoxy C1-3 alkylene group" include a fluoro group, chloro Halogeno groups such as group, bromo group and iodo group; C1 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group and t-butyl group ~6 alkyl group; or C1~6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group and 1-fluoro-n-butyl group are preferred.

In the present invention, preferred G is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 3-10 a membered heterocyclyl group, a group represented by R ^b --O--CO--, a group represented by R ^{c R d N--, a group represented by R c} ^{R d} ^N ^-- CO--, and R ^a --CO-- A group represented by O—, a group represented by R ^a —CO—NR ^e —, a group represented by R ^b —O—CO—NR ^e —, a group represented by R ^c R ^d N—CO—O— a group represented by R ^c R ^d N—CO—NR ^e —, a group represented by R ^c R ^d N—CS—NR ^e —, a group represented by R ^b SO ₂ —NR ^e — group, a group represented by R ^a ON=CR ^f -, or a group represented by R ^h R ⁱ C=NO-.

[X ³ and R ^N1 and R ^N2 other than X ³ above]
Furthermore, X ³ is a group represented by R ^N1 O—, a group represented by R ^N1 —CO—O—, a group represented by R ^N1 —O—CO—O—, R ^N1 R ^N1 N— a group represented by CO--O--, a group represented by R ^N1 --CS--O--, a group represented by R ^N1 R ^N1 N--CS--O--, a group represented by R ^N1 R ^N2 N-- , a group represented by R ^N1 -CO-NR ^N2 -, a group represented by R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, R ^N1 R A group represented by ^N1 N—CO—NR ^N2 —, a group represented by R ^N1 R ^N1 N—CO—CO—NR ^N2 —, a group represented by R ^N1 —CS—NR ^N2 —, R ^N1 R A group represented by ^N1 N--CS--NR ^N2 --, a group represented by R ^N1 SO ₂ --NR ^N2 --, or a group represented by R ^N1 --C(=NR ^N1 )--NR ^N2 --.

R ^N1 and R ^N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 may together form a divalent organic group.

Examples of the "linear C1-6 alkyl group" for R ^N1 and R ^N2 include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group.
The "linear C2-6 alkenyl group" for R ^N1 and R ^N2 includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl and 5-hexenyl groups.
The "linear C2-6 alkynyl group" for R ^N1 and R ^N2 includes an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group and the like.
Examples of the "4-membered heterocyclyl group" for R ^N1 and R ^N2 include an azetidinyl group and an oxetanyl group.
Specific examples of other substituents for R ^N1 and R ^N2 are the same as those exemplified for X ¹ .

[ ^X4 ]
X ⁴ is a group represented by QA-, a group represented by QA-B-, a group represented by QB-A-, a group represented by Q-SO ₂ -NR ^N3 , a group represented by Q—C(R ⁷ )=N—, a group represented by Q—NR ^N3 —SO ₂ —, a group represented by QN=C(R ⁷ )—, or Q— A group represented by B- is shown.

[A]
A is a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or carbonyl indicates a group.

Examples of the "C1-6 alkylene group" for A include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
The "C2-6 alkenylene group" in A includes a vinylene group (-CH=CH-), a divinylene group (-CH=CH-CH=CH-), a propenylene group (-CH=CH-CH ₂ -, -CH ₂ -CH=CH-) and the like.
Examples of the "C2-6 alkynylene group" for A include an ethynylene group (-C≡C-), a propynylene group (-CH ₂ -C≡C-, -C≡C-CH ₂ -), and the like. .
Examples of the "C3-6 cycloalkylene group" for A include 1,2-cyclopropylene group, 1,2-cyclobutanediyl group, 1,3-cyclobutanediyl group and the like.

In the present invention, A is preferably a substituted or unsubstituted C1-6 alkylene group or a substituted or unsubstituted C2-6 alkenylene group.
Examples of substituents on the C1-6 alkylene group or C2-6 alkenylene group include one or more substituents selected from the following group of substituents (hereinafter, this substituent is denoted by the symbol "Ga" can be expressed as ).
Moreover, when there are two or more substituents (Ga), two of them may be combined to form a divalent organic group. Substituent groups are shown below.
halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, mercapto group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted Or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3 to 6-membered heterocyclyl group, substituted or unsubstituted 3- to 6-membered heterocyclyloxy group, nitro group, cyano group, group represented by R ^a1 —CO—, carboxy group, R ^b1 —O—CO— a group represented by R ^c1 R ^d1 N—, a group represented by R ^c1 R ^d1 N—CO—, a group represented by R ^a1 —CO—O—, R ^a1 —CO— a group represented by NR ^e1 —, a group represented by R ^b1 —O—CO—O—, a group represented by R ^b1 —O—CO—NR ^e1 —, R ^c1 R ^d1 N—CO—O— a group represented by R ^c1 R ^d1 N—CO—NR ^e1 — a group represented by R ^b1 SO ₂ —NR ^e1 — a group represented by R ^c1 R ^d1 N—SO ₂ — group, R ^{a1 ON} =CR ^f1 - group, R ^g1 R ^h1 C=NO- group, oxo group (O=), thioxo group (S=), R ^a1 - a divalent group represented by N=, a divalent group represented by R ^{a1 ON} =, a divalent group represented by R ^c1 R ^d1 NN=, R ^a1 -CO-NR ^e1 -N=, a divalent group represented by R ^b1 -O-CO-NR ^e1 -N=, a divalent group represented by R ^b1 SO ₂ -NR ^e1 -N= base.

In the above substituent groups, each R ^a1 is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R ^b1 each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
Each R ^c1 is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
Each R ^d1 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, wherein R ^c1 and R ^d1 are together A divalent organic group may be formed.
R ^e1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R ^f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
R ^g1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, substituted or an unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R ^h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, wherein R ^g1 and R ^h1 may together form a divalent organic group.

Examples of the "halogeno group" in Ga include a fluoro group, a chloro group, a bromo group, an iodine group, and the like.

The "C1-6 alkyl group" in Ga may be linear or branched. The "C1-6 alkyl group" in Ga includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s- Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.

The "C2-6 alkenyl group" in Ga includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group , 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.

The "C2-6 alkynyl group" in Ga includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group , 1,1-dimethyl-2-butynyl group, and the like.

The "C1-6 alkoxy group" for Ga includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, Examples include s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of the "C2-6 alkenyloxy group" for Ga include a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group.
Examples of the "C2-6 alkynyloxy group" for Ga include an ethynyloxy group and a propargyloxy group.

Examples of the "C1-6 alkylthio group" for Ga include methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, i-propylthio and the like.
Examples of the "C1-6 alkylsulfinyl group" in Ga include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
Examples of the "C1-6 alkylsulfonyl group" for Ga include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.

Ga "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkynyloxy group ”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” or “C1-6 alkylsulfonyl group” include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group. hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phenyl group, C6-10 aryl group such as naphthyl group; C1-6 alkyl group such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group , a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, a C6-10 aryl group substituted with one or more substituents; or a cyano group.

Examples of the "C3-6 cycloalkyl group" for Ga include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
Examples of the "C3-6 cycloalkyloxy group" for Ga include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.

Examples of the "C6-10 aryl group" for Ga include a phenyl group, a naphthyl group, an indenyl group, an indanyl group and a tetralinyl group.
Examples of the "C6-10 aryloxy group" for Ga include a phenoxy group and a naphthoxy group.

Examples of the "C6-10 arylthio group" in Ga include a phenylthio group and a naphthylthio group.
Examples of the "C6-10 arylsulfinyl group" for Ga include a phenylsulfinyl group and a naphthylsulfinyl group.
Examples of the “C6-10 arylsulfonyl group” for Ga include a phenylsulfonyl group and a naphthylsulfonyl group.

The "3- to 6-membered heterocyclyl group" for Ga is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different. Examples of the "3- to 6-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .

3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, A dioxolanyl group, a dioxanyl group and the like can be mentioned.
Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.

The "3- to 6-membered heterocyclyloxy group" in Ga has a structure in which a 3- to 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.

Ga "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 Arylsulfinyl group", "C6-10 arylsulfonyl group", "3- to 6-membered heterocyclyl group" or "3- to 6-membered heterocyclyloxy group" include a fluoro group, a chloro group, halogeno groups such as bromo group and iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group , C1-6 alkyl groups such as n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro -C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group and 4-methoxyphenyl a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 A C6-10 aryl group substituted with any one or more substituents of a haloalkoxy group; or a cyano group is preferred.

In the "group represented by R ^a1 -CO-" for Ga, R ^a1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted It represents a C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.

The "C1-6 alkyl group" for R ^a1 includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Examples of the “C2-6 alkenyl group” for R ^a1 include a vinyl group and a 1-propenyl group.
Examples of the “C2-6 alkynyl group” for R ^a1 include an ethynyl group and a 1-propynyl group.
Examples of substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in R ^a1 include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phenyl group, naphthyl a C6-10 aryl group such as a group; a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group such as a 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group; or a C6-10 aryl group substituted with one or more substituents; or a cyano group.

Examples of the "C3-6 cycloalkyl group" for R ^a1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the “C6-10 aryl group” for R ^a1 include a phenyl group and a naphthyl group.

The “5- to 6-membered heterocyclyl group” for R ^a1 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- to 6-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.

Examples of substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- to 6-membered heterocyclyl group" for R ^a1 include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. C1 ~ 6 alkyl group of; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, C1 ~ 6 haloalkyl group such as 1-fluoro-n-butyl group; hydroxyl group; methoxy group , ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy groups such as t-butoxy group; 2-chloro-n-propoxy group, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group and 4-chlorophenyl group , 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc., a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group C6-10 aryl groups substituted with one or more substituents; or cyano groups are preferred.

Specific examples of the "group represented by R ^a1 -CO-" include a formyl group and an acetyl group.

In the "group represented by R ^b1 -O-CO-" for Ga, R ^b1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ~6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Specific examples of the substituent for R ^b1 are the same as those exemplified for R ^a1 .

Specific examples of the "group represented by R ^b1 -O-CO-" include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group and the like.

In the "group represented by R ^c1 R ^d1 N-" for Ga, R ^c1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted A C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and R ^d1 is , a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent for R ^c1 or R ^d1 are the same as those exemplified for R ^a1 .
Here, R ^c1 and R ^d1 may together form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; methyl group, ethyl group, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.

Specific examples of the "group represented by R ^c1 R ^d1 N-" include an amino group, a methylamino group and a dimethylamino group.

In the "group represented by R ^c1 R ^d1 N--CO--" in Ga, R ^c1 and R ^d1 have the same meanings as in the above "group represented by R ^c1 R ^d1 N--".
Specific examples of the “group represented by R ^c1 R ^d1 N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, and an N-(i-propyl )—N-methylaminocarbonyl group and the like.

In the "group represented by R ^a1 -CO-O-" for Ga, R ^a1 has the same meaning as in the above "group represented by R ^a1 -CO-".
Specific examples of the "group represented by R ^a1 -CO-O-" include an acetyloxy group.

In the "group represented by R ^a1 -CO-NR ^e1 -" for Ga, R ^a1 has the same meaning as in the above "group represented by R ^a1 -CO-".
R ^e1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent for R ^e1 are the same as those exemplified for R ^a1 .
Specific examples of the "group represented by R ^a1 -CO-NR ^e1 -" include an acetylamino group.

In the “group represented by R ^b1 —O—CO—O—” for Ga, R ^b1 has the same meaning as in the above “group represented by R ^b1 —O—CO—”.
Specific examples of the "group represented by R ^b1 -O-CO-O-" include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

In the “group represented by R ^b1 —O—CO—NR ^e1 —” for Ga, R ^b1 has the same meaning as in the above “group represented by R ^b1 —O—CO—”. R ^e1 has the same meaning as in the above “group represented by R ^b1 —CO—NR ^e1 —”.
Specific examples of the “group represented by R ^b1 —O—CO—NR ^e1 —” include a methoxycarbonylamino group.

In the “group represented by R ^c1 R ^d1 N—CO—O—” for Ga, R ^c1 and R ^d1 have the same meanings as those in the above “group represented by R ^c1 R ^d1 N—” .
Specific examples of the “group represented by R ^c1 R ^d1 N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.

In the "group represented by R ^c1 R ^d1 N-CO-NR ^e1 -" for Ga, R ^c1 and R ^d1 have the same meanings as those in the above "group represented by R ^c1 R ^d1 N-". show. R ^e1 has the same meaning as in the above “group represented by R ^a1 —CO—NR ^e1 —”.
Specific examples of the “group represented by R ^c1 R ^d1 N—CO—NR ^e1 —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.

In the “group represented by R ^b1 SO ₂ —NR ^e1 —” for Ga, R ^b1 has the same meaning as in the above “group represented by R ^b1 —O—CO—”. R ^e1 has the same meaning as in the above “group represented by R ^a1 —CO—NR ^e1 —”.
Specific examples of the “group represented by R ^b1 SO ₂ —NR ^e1 —” include a methanesulfonylamino group and the like.

In the “group represented by R ^c1 R ^d1 N—SO ₂ —” for Ga, R ^c1 and R ^d1 have the same meanings as those in the above “group represented by R ^c1 R ^d1 N—”.
Specific examples of the “group represented by R ^c1 R ^d1 N—SO ₂ —” include an N,N-dimethylaminosulfonyl group.

In the "group represented by R ^a1 ON=CR ^f1 -" for Ga, R ^a1 has the same meaning as in the above "group represented by R ^a1 -CO-".
R ^f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent for R ^f1 are the same as those exemplified for ^Ra .
Specific examples of the "group represented by R ^{a1 ON} =CR ^f1 -" include (hydroxyimino)methyl group and (ethoxyimino)methyl group.

In the "group represented by R ^g1 R ^h1 C=NO-" for Ga, R ^g1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted represents a substituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, R ^h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent for R ^g1 or R ^h1 are the same as those exemplified for R ^a1 .
Here, R ^g1 and R ^h1 may together form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
Specific examples of the "group represented by R ^g1 R ^h1 C=NO-" include a (propan-2-ylideneamino)oxy group.

In the "divalent group represented by R ^a1 -N=" for Ga, R ^a1 has the same meaning as in the above "group represented by R ^a1 -CO-".
Specific examples of the "divalent group represented by R ^a1 -N=" include an imino group (HN=) and a methylimino group.

In the “divalent group represented by R ^a1 ON=” for Ga, R ^a1 has the same meaning as in the above “group represented by R ^a1 —CO—”.
Specific examples of the "divalent group represented by R ^{a1 ON} =" include an N-hydroxyimino group and an N-methoxyimino group.

In the "divalent group represented by R ^c1 R ^d1 NN=" for Ga, R ^c1 and R ^d1 have the same meanings as those in the above "group represented by R ^c1 R ^d1 N-". show.
Specific examples of the "divalent group represented by R ^c1 R ^d1 N--N=" include a 2,2-dimethylhydrazinylidene group.

In the "divalent group represented by R ^a1 -CO-NR ^e1 -N=" in Ga, R ^a1 has the same meaning as in the above "group represented by R ^a1 -CO-". R ^e1 has the same meaning as in the above “group represented by R ^a1 —CO—NR ^e1 —”.

In the “divalent group represented by R ^b1 —O—CO—NR ^e1 —N=” for Ga, R ^b1 has the same meaning as in the above “group represented by R ^b1 —O—CO—” indicate. R ^e1 has the same meaning as in the above “group represented by R ^a1 —CO—NR ^e1 —”.

In the “divalent group represented by R ^b1 SO ₂ —NR ^e1 —N=” in Ga, R ^b1 has the same meaning as in the above “group represented by R ^b1 —O—CO—” . R ^e1 has the same meaning as in the above “group represented by R ^a1 —CO—NR ^e1 —”.

When there are two or more substituents (Ga), the divalent organic group that can be formed by two of them together includes a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxy C1-4 An alkylene group, a substituted or unsubstituted oxy C2-3 alkyleneoxy group, or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group can be mentioned.
Examples of the "C1-5 alkylene group" include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
Examples of the "oxy C1-4 alkylene group" include an oxymethylene group and an oxydimethylene group.
Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethylenoxy group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on the "C1-5 alkylene group", "oxy-C1-4 alkylene group", "oxy-C2-3 alkyleneoxy group" and "C1-3 alkyleneoxy C1-3 alkylene group" include a fluoro group, chloro Halogeno groups such as group, bromo group and iodo group; C1 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group and t-butyl group ~6 alkyl group; or C1~6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group and 1-fluoro-n-butyl group are preferred.

In the present invention, preferred Ga includes a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a substituted or unsubstituted C3 ~ 6 cycloalkyloxy group, substituted or unsubstituted C6 ~ 10 aryloxy group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a group represented by R ^a1 -CO-O-, oxo A group (O=) or a divalent group represented by R ^{a1 ON} = can be mentioned.
In this case, a preferred substituted or unsubstituted 5- to 6-membered heterocyclyloxy group is a tetrahydro-2H-pyran-4-yl group.

In the present invention, more preferred Ga includes a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, R ^a1 - A group represented by CO—O—, an oxo group (O=), or a divalent group represented by R ^{a1 ON} = can be mentioned.

[B]
B is an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR ^N3 -, and R ^N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a formyl group, or It represents a substituted or unsubstituted C1-6 alkylcarbonyl group.

The “C1-6 alkyl group” in R ^N3 may be linear or branched. The "C1-6 alkyl group" in R ^N3 includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Examples of the “C1-6 alkylcarbonyl group” for R ^N3 include an acetyl group, a propionyl group, a butyryl group, an i-propylcarbonyl group and the like.

The substituents on the "C1-6 alkyl group" and "C1-6 alkylcarbonyl" in R ^N3 include a fluoro group, a chloro group, a bromo group, a halogeno group such as an iodo group; a hydroxyl group; a methoxy group, an ethoxy group, C1-6 alkoxy groups such as n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy group, 2,3- C1-6 haloalkoxy groups such as dichlorobutoxy group and trifluoromethoxy group; (C1-6 alkylideneamino)oxy groups such as (ethylideneamino)oxy group and propane-2-ylideneamino)oxy group; cyclopropyl group and cyclobutyl group , cyclopentyl group, C3-6 cycloalkyl group such as cyclohexyl group; phenyl group, C6-10 aryl group such as naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethyl any one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group such as a phenyl group and a 4-trifluoromethoxyphenyl group; 5-membered substituted C6-10 aryl group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. ring heteroaryl group; a 5-membered ring substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group heteroaryl group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered heteroaryl group such as triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or A 6-membered heteroaryl group substituted with one or more substituents selected from C1-6 haloalkoxy groups; or a cyano group is preferred.

[ ^R7 ]
R ⁷ represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
The “C1-6 alkyl group” for R ⁷ may be linear or branched. The "C1-6 alkyl group" for R ⁷ includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Substituents on the "C1-6 alkyl group" in R ⁷ include halogeno groups such as fluoro, chloro, bromo and iodo groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group and i-propoxy group. , n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, etc. C1 ~ 6 haloalkoxy group; (ethylideneamino) oxy group, propane-2-ylideneamino) oxy group such as (C1 ~ 6 alkylideneamino) oxy group; cyclopropyl group, cyclobutyl group, cyclopentyl group, C3 such as cyclohexyl group ~6 cycloalkyl group; phenyl group, C6 ~ 10 aryl group such as naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl a C6-10 aryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, such as a group; five-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl; 5-membered heteroaryl group substituted with one or more substituents selected from an alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a pyridyl group, a pyrazinyl group , a pyrimidinyl group, a pyridazinyl group, a 6-membered heteroaryl group such as a triazinyl group; any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group A 6-membered heteroaryl group substituted with one or more substituents; or a cyano group is preferred.

[Q]
Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.

Examples of the "C6-10 aryl group" for Q include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group, and the like.

The “5- to 10-membered heterocyclyl group” for Q is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur atoms as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic.
Examples of the "5- to 10-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .

Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc. 10-membered heteroaryl group;
Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl group; 9-membered partially unsaturated ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;

Examples of substituents on the "C6-10 aryl group" or "5- to 10-membered heterocyclyl group" in Q include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, C1-6 alkyl groups such as n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; vinyl group, etc. C2-6 alkenyl group of; C2-6 alkynyl group such as ethynyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group and the like C1-6 haloalkyl group; C1-6 alkoxy C1-6 alkyl group such as methoxymethyl group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i C1-6 alkoxy groups such as -butoxy group and t-butoxy group; hydroxy C1-6 alkoxy groups such as hydroxyethoxy group; C1-6 alkoxyalkoxy groups such as methoxymethoxy group and methoxyethoxy group; trimethylsilyloxyethoxy group, t -Tri-C1-6 alkyl-substituted silyloxy C1-6 alkoxy groups such as butyldimethylsilyloxyethoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10 aryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 halo C6-10 aryl substituted with any one or more substituents of an alkoxy group)C1-6 alkoxy group; 5-membered ring heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, 5-membered heteroaryl)C1-6 alkoxy group; 6-membered heteroaryl C1-6 substituted with one or more substituents selected from a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group Alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) 6-membered heteroaryl substituted with one or more substituents ) C1-6 alkoxy group; C1-6 alkylthio group such as methylthio group and ethylthio group; C1-6 alkyl group such as methylsulfinyl group and ethylsulfinyl group sulfinyl group; methylsulfonyl group, C1-6 alkylsulfonyl group such as ethylsulfonyl group; trifluoromethylthio group, C1-6 haloalkylthio group such as 2,2,2-trifluoroethylthio group: trifluoromethylsulfinyl group, C1-6 haloalkylsulfinyl groups such as 2,2,2-trifluoroethylsulfinyl group; trifluoromethylsulfonyl group, C1-6 haloalkylsulfonyl groups such as 2,2,2-trifluoroethylsulfonyl group; cyclopropyl group, C3-6 cycloalkyl group such as cyclobutyl group and cyclopentyl group; any one or more of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group C3 ~ 6 cycloalkyl group substituted with a substituent of; cyclopropenyl group, cyclobutenyl group, C3 ~ 6 cycloalkenyl group such as cyclopentenyl group; phenyl group, C6 ~ 10 aryl group such as naphthyl group; 4-methyl C1-6 alkyl groups, C1-6 alkoxy groups such as phenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, C6-10 aryl group substituted with one or more substituents selected from halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 3-4 groups such as aziridinyl group, epoxy group, azetidinyl group and oxetanyl group saturated membered heterocyclyl group; 3-4 substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5- to 6-membered saturated heterocyclyl groups such as a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group; A 5- to 6-membered saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl 5-membered ring heteroaryl group such as group, tetrazolyl group; any one or more substituents in C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5-membered heteroaryl group substituted with; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered heteroaryl group such as triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a C1-6 haloalkyl group, or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 haloalkoxy group; pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group , 5-membered partially unsaturated heterocyclyl group such as isoxazolinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5-membered partially saturated heterocyclyl group substituted with one or more substituents; 6-membered partially unsaturated heterocyclyl group such as dihydropyranyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 ~6 haloalkyl group, or a 6-membered partially saturated heterocyclyl group substituted with one or more substituents of a C1~6 haloalkoxy group;
a group represented by R ^Q1 —CO— (wherein R ^Q1 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, C1-6 alkyl group substituted with one or more substituents of a phenyl group or a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a haloalkyl group or a C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from ∼6 haloalkyl group or C1-6 haloalkoxy group)C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or a C3-6 cycloalkyl group substituted with one or more substituents of a cyano group; a C6-10 aryl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or C6-10 aryl group substituted with one or more substituents of any one of C1-6 haloalkoxy groups; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, a 5- to 6-membered heteroaryl group substituted with one or more substituents; The same applies to R ^Q1 below.);
carboxy group;
A group represented by R ^Q2 —O—CO— (wherein R ^Q2 is a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl or a C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl C6-10 aryl)C1-6 alkyl group substituted with one or more substituents, or C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from a 6-haloalkyl group or a C1-6 haloalkoxy group) C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl group C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or C3-6 cycloalkyl group substituted with cyano group; C6-10 aryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group a C6-10 aryl group substituted with one or more substituents; a 5- to 6-membered heteroaryl group; or; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1 A 5- to 6-membered heteroaryl group substituted with one or more substituents selected from ^∼6 haloalkoxy groups;
A group represented by R ^Q1 R ^Q1 N— (R ^Q1 in the formula may be the same or different. Together, R ^Q1 may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.);
A group represented by R ^Q1 R ^Q1 N—CO— (in the formula, R ^Q1 may be the same or different. R ^Q1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a A methyleneoxydimethylene group may be formed.);
a group represented by R ^Q1 -CO-O-; a group represented by R ^Q1 -CO-NR ^Q3 - (wherein R ^Q3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; The same applies to R ^Q3 below.);
a group represented by R ^Q2 -O-CO-O-; a group represented by R ^Q2 -O-CO-NR ^Q3 -; a group represented by R ^Q1 R ^Q1 N-CO-O- (in the formula R ^Q1 may be the same or different, and R ^Q1 may together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.);
A group represented by R ^Q1 R ^Q1 N—CO—NR ^Q3 — (R ^Q1 in the formula may be the same or different. Together, R ^Q1 may be a trimethylene group, a tetramethylene group, a pentamethylene group, , or may form a dimethyleneoxydimethylene group); a group represented by R ^Q2 SO ₂ —NR ^Q3 —; a group represented by R ^Q1 R ^Q1 N—SO ₂ — (in the formula, R ^Q1 may be the same or different, and R ^Q1 may together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.);
a group represented by R ^Q1 -ON=C(R ^Q4 )- (wherein R ^Q4 represents a hydrogen atom or a C1-6 alkyl group); (R ^Q1 ) ₂ C=N-O- (R ^Q1 in the formula may be the same or different. R ^Q1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.);
A pentafluorosulfanyl group, a trimethylsilylethynyl group, a nitro group, or a cyano group are preferred.
Furthermore, an oxo group is also preferred as a substituent on the "5- to 10-membered heterocyclyl group".

〔salt〕
Salts of compound (I) are not particularly limited as long as they are agriculturally and horticulturally acceptable salts. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals; salts of organic bases such as triethylamine, tributylamine, pyridine and hydrazine; and ammonium salts.

〔Production method〕
The method for producing compound (I) or a salt of compound (I) is not limited. For example, compound (I) or a salt of compound (I) of the present invention can be obtained by known methods such as those described in Examples. Also, a salt of compound (I) can be obtained from compound (I) by a known method.

[Manufacturing intermediate]
In preparing the pyridazinone compound of the present invention, the compound represented by the following formula (II) or a salt thereof can be a production intermediate.

In formula (II),
Y represents an oxygen atom or a sulfur atom;
X ¹ and X ² are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6- 10 arylsulfonyl group, substituted or unsubstituted 5- to 6-membered heterocyclyl group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, nitro group, cyano group, group represented by R ¹ -CO- , a carboxy group, a group represented by R ² —O—CO—, a group represented by R ³ R ⁴ N—, a group represented by R ³ R ⁴ N—CO—, R ¹ —CO—O— a group represented by R ¹ -CO-NR ⁵ -, a group R ² -O-CO-O-, a group R ² -O-CO-NR ⁵ - , a group represented by R ³ R ⁴ N—CO—O—, a group represented by R ³ R ⁴ N—CO—NR ⁵ —, a group represented by R ² SO ₂ —NR ⁵ —, R ³ a group represented by R ⁴ N--SO ₂ --, a group represented by R ¹ ON=CR ⁶ --, a group represented by R ³ R ⁴ N--N=CR ⁶ --, or R ¹ --N represents a group represented by =CR ⁶ -;
R ¹ is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R ² is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R ³ is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
each R ⁴ independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein R ³ and R ⁴ may together form a divalent organic group,
each R ⁵ independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R ⁶ is a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted a substituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group;
X ³ is a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R ¹ -CO A group represented by -, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4- to 6-membered heterocyclyl group, R ^N1 O- a group represented by R ^N1 --CO--O--, a group represented by R ^N1 --O--CO--O--, a group represented by R ^N1 R ^N1 N--CO--O--, and R ^N1 A group represented by -CS-O-, a group represented by R ^N1 R ^N1 N-CS-O-, a group represented by R ^N1 R ^N2 N-, a group represented by R ^N1 -CO-NR ^N2 - a group represented by R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-NR ^N2 - a group represented by R ^N1 R ^N1 N—CO—CO—NR ^N2 —, a group represented by R ^N1 —CS-NR ^N2 —, and a group represented by R ^N1 R ^N1 N—CS-NR ^N2 — a group represented by R ^N1 SO ₂ —NR ^N2 —, or a group represented by R ^N1 —C(=NR ^N1 )—NR ^N2 —,
R ^N1 and R ^N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 may together form a divalent organic group;
X ⁵ represents a group represented by HO-A-, a C1-6 alkoxycarbonyl group, or a halogeno group,
A is a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or carbonyl indicates a group.

Each symbol in formula (II) has the same meaning as those in formula (I).
The "C1-6 alkoxycarbonyl group" for X ⁵ includes a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, a t-butoxycarbonyl group, and the like. .
Examples of the "halogeno group" for ^X5 include a fluoro group, a chloro group, a bromo group, an iodo group and the like.
The compound of formula (II) is preferably a compound in which X ² is a group represented by R ¹ ON=CR ⁶ - or a salt thereof.

[Salt of production intermediate and production method]
Examples of the salt of the production intermediate represented by formula (II) are the same as the salt of the compound represented by formula (I).
Moreover, the production method of the production intermediate represented by formula (II) is not limited. For example, it can be obtained by a known method as described in Examples. Also, a salt of a production intermediate can be obtained from compound (II) by a known method.

[Fungicide for agriculture and horticulture]
The agricultural and horticultural fungicide of the present invention contains as an active ingredient at least one selected from compound (I) and salts thereof. The amount of compound (I) or a salt thereof contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it exhibits a fungicidal effect.

The agricultural and horticultural fungicides of the present invention are suitable for a wide variety of filamentous fungi such as Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, zygotes. It can be used to control plant diseases caused by fungi belonging to Zygomycetes.

Examples of plant diseases (pathogens) targeted for control are shown below.
Sugar beet: brown spot (Cercospora beticola), cochlioides (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), spot Peanuts: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum ), rust (Alternaria alternata), white silk (Sclerotium rolfsii), black stain (Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc. Cucumber: powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis) , Mycosphaerella melonis, Fusarium oxysporum, Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum orbiculare, Cladosporium cucumerinum, Brown spot Corynespora cassiicola, Pythium debaryanum, Rhizoctonia solani Kuhn, Phomopsis sp., Pseudomonas syringae pv. Lachrymans, etc. Tomatoes: Botrytis cinerea, leaves Mold (Cladosporium fulvum), plague (Phytophthora infestans), wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), ring spot (Alternaria solani), Pseudocercospora fuligena, Ralstonia solanacearum, Sclerotinia sclerotiorum, etc. Eggplant: Botrytis cinerea, Corynespora melongenae, Erysiphe cichoracearum), Mycovellosiella nattrassii, Sclerotinia sclerotiorum, Verticillium dahliae, Phomopsis vexans, etc. Pepper: Phytophthora capsici, Botrytis cinerea , Sclerotinia sclerotiorum, Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense, Leveillula taurica Strawberry: Botrytis cinerea, Sphaerotheca humuli , Colletotrichum acutatum, Colletotrichum fragariae, Phytophthora cactorum, Rhizopus stolonifer, Fusarium oxysporum, Verticillium dahliae, Sclerotinia sclerotiorum, etc. Onions: Gray Botrytis allii, Botrytis cinerea, Botrytis squamosa, Peronospora destructor, Phytophthora porri, Ciborinia allii, Small fungi nucleus rot (Botrytis squamosa), dry rot (Fusarium oxysporum), red root rot (Pyrenochaeta terrestris), black rot sclerotium (Sclerotium cepivorum), rust (Puccinia allii), white silk disease (Sclerotium rolfsii), etc. Green onions: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black rot (Sclerotium cepivorum), rust (Puccinia allii), leaf blight (Botrytis squamosa), white silk disease (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc. Cabbage: clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. campestris), black spot (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), mildew (Peronospora parasitica), sclerotinia (Sclerotinia sclerotiorum) ), Black soot (Alternaria brassicicola), Gray mold (Botrytis cinerea), Root rot (Phoma lingam), Pythium aphanidermatum, Pythium ultimum, White rust (Albugo macrospora), etc. Lettuce: rot ( Pseudomonas cichorii, Pseudomonas marginalis, Pectobacterium carotovorum, Bremia lactucae, Botrytis cinerea, Sclerotinia sclerotiorum, Mirafiori lettuce big-vein ophiovirus, Fusarium oxysporum, Rhizoctonia solani, Golovinomyces orontii, etc. Green beans: Sclerotinia sclerotiorum, Botrytis cinere a), Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc. Peas: Mycosphaerella blight, Botrytis cinerea, Sclerotinia sclerotiorum, Erysiphe pisi )Such

Apples: powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), monilia (Monilinia mali), black spot (Mycosphaerella pomi), rot (Valsa mali), leaf spot (Alternaria mali), scab (Gymnosporangium) yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena), purple leaf spot (Helicobasidium mompa), White leaf disease (Rosellinia necatrix), Gray mold (Botrytis cinerea), Fire blight (Erwinia amylovora), Silver leaf disease (Chondrostereum purpureum), Root canker (Rhizobium radiobacter, Rhizobium rhizogenes) Plum: Cladosporium carpophilum, Botrytis cinerea, Monilinia mumecola, Peltaster sp., Taphrina pruni, Phloeosporella padi Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), horn spot (Cercospora kaki), leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), soot spot (Zygophiala) jamaicensis), etc. Peach: Monilinia fructicola, Monilia fructigena, Cladosporiumcarpophilum, Phomopsis sp., Xanthomonas campestris pv. pruni, Taphrina deformans, charcoal Colletotrichum gloeosporioides, Phloeosporella padi, Coriolus versicolor, etc. Almonds: Monilinia laxa, Stigmina carpophila, Cladosporium carpophilum, leaf blisters Polystigma rubrum, Alternaria alternata, Colletotrichum gloeospoides, etc. Cherry: Monilinia fructicola, Colletotrichum acutatum, Alternaria sp., young fruit Sclerotinia (Monilinia kusanoi), brown pit (Mycosphaerella cerasella), powdery mildew (Podosphaera tridactyla), etc. Grapes: Botrytis cinerea, powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum) acutatum), downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), Snow white (pathogen unidentified), root cancer (Rhizobium radiobacter, Rhizobium vitis), etc. Pear: Venturia nashicola, Gymnosporangium asiaticum, Alternaria kikuchiana, Ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown spot (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: Pestalotiops is longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blister (Exobasidium reticulatum), red scorch (Pseudomonas syringae), blast (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcettii) , Penicillium italicum, Penicillium digitatum, Botrytis cinerea, Diaporthe citri, Xanthomonas campestris pv. Citri, Powdery mildew (Oidium sp.), Late blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc. Kiwifruit: Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava, Pseudomonas syringae, Botrytis cinerea, fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), Pseudocercospora actinidiae, etc. Olive: Colletotrichum acutatum, Colletotrichum gloeosporioides, Peacock spot (Spilocaea oleaginea), etc. Chestnut: Colletotrichum gloeosporioides, etc.

Wheat: Powdery mildew (Blumeria graminis f.sp. tritici), Fusarium head blight (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), Fusarium rust (Puccinia recondita), Yellow rust (Puccinia striiformis), Pythium iwayamai, Monographella nivalis, Pseudocercosporella herpotrichoides, Septoria tritici, Leptosphaeria nodorum, Typhula incarnata), Myriosclerotinia borealis, Gaeumannomyces graminis, Claviceps purpurea, Tilletia caries, Ustilago nuda, Pyricularia grisea ), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Barley: Pyrenophora graminea, Pyrenophora teres ), Rhynchosporium secalis, Naked smut (Ustilago tritici, U.nuda), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp. Rice: Pyricularia oryzae, Rhizoctonia solani, Gibberella fujikuroi, Cochliobolus miyabeanus, Pythiumg raminicola), Xanthomonas oryzae, Burkholderia plantarii, Acidovorax avenae, Burkholderia glumae, Cercospora oryzae, Rice blight (Ustilaginoidea virens), Brown rice (Alternaria alternata, Curvularia intermedia), Alternaria padwickii, Epicoccum purpurascens, etc. Tobacco: Sclerotinia sclerotiorum, Erysiphe cichoracearum, plague ( Phytophthora nicotianae), etc. Tulips: Botrytis cinerea, Botrytis tulipae, Rhizoctonia solani, Fusarium oxysporum, Rhizoctonia solani, etc. Rose: Black star Diplocarpon rosae, powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Peronospora danica), Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum, Rhizoctonia solani, Fusarium solani, etc. Gerbera: Botrytis cinerea ), powdery mildew (Podosphaera xanthii), etc. Lily: leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc. Sunflower: downy mildew (Pla smopara halstedii), Sclerotinia sclerotiorum, Botrytis cinerea, etc. Bent grass: Sclerotinia borealis, large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), dollar spot ( Sclerotinia homoeocarpa), Pyricularia sp., Pythium aphanidermatum, Colletotrichum graminicola, etc. Orchard grass: Powdery mildew (Erysiphe graminis), etc. Soybean: Purpura (Cercospora kikuchii), downy mildew Peronospora manshurica, Phytophthora sojae, Phakopsora pachyrhizi, Sclerotinia sclerotiorum, Colletotrichum truncatum, Botrytis cinerea, Elsinoe glycines ), Black spot (Diaporthe phaseolorum var. sojae), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Potatoes: Phytophthora infestans ), Alternaria solani, Thanatephorus cucumeris, Verticillium albo-atrum, V. dahliae, V. nigrescens, Pectobacterium atrosepticum, Pectobacterium carotovorum, Gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia (Sclerotinia sclerotiorum), etc. sporium dioscoreae, Colletotrichum gloeosporioides, Penicillium sclerotigenum, etc. Sweet potato: Helicobasidium mompa, Fusarium oxysporum, etc. Taro: Phytophthora colocasiae, Rhizoctonia solani), etc. Ginger: Root rot (Pythium ultimum, Pythium myriotylum), White star disease (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum) aenigma), canker (Xanthomonas campestris), shaft rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), gray mold (Botrytis cinerea), etc. Rapeseed: Sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae), powdery mildew (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), downy mildew (Peronospora parasitica), etc. Coffee: rust (Hemileia vastatrix), anthracnose ( Coletotrichum coffeanum), brown eye disease (Cercospora coffeicola), etc. Sugarcane: Brown rust (Puccinia melanocephala), etc. Corn: Gloeocercospora sorghi, rust (Puccinia sorghi), southern rust (Puccinia polysora), smut (Ustilago) maydis), sesame leaf blight (Cochliobolus hetero strophus), Setosphaeria turcica, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. sp.), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hops: Downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold disease (Botrytis cinerea), etc.

[Nematicide]
The pyridazinone compound of the present invention is also excellent in controlling effect on various nematodes that affect plant growth.
The nematicide of the present invention contains at least one selected from compound (I) and salts thereof as an active ingredient. The amount of compound (I) or a salt thereof contained in the nematicide of the present invention is not particularly limited as long as it exhibits a nematode control effect.

Specific examples of various plant parasitic nematodes that can be controlled by the nematicide of the present invention are shown below. (1) Tylenchida
(a) Anguinidae, for example, Anguina spp., Anguina funesta, Anguina tritici; Ditylenchus spp., Imogusare nematode ( Ditylenchus destructor), Ditylenchus dipsaci, Ditylenchus myceliophagus;
(b) Aphelenchoides family (Aphelenchoididae), for example, Aphelenchoides spp., Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi; Bursa Bursaphelenchus xylophilus, of the genus Bursaphelenchus spp.;
(c) Belonolaimidae, e.g., Belonolaimus spp., Belonolaimus longicaudatus; Tylenchorhynchus spp., Tylenchorhynchus claytoni , Tylenchorhynchus dubius;
(d) of the family Criconematidae, such as Criconema mutabile;
(e) of the family Dolichoodoridae, such as Dolichoodorus mediterraneus;
(f) Ecphyadophoridae, for example, Ecphyadophora tenuissima
(g) Hemicycliophoridae, such as Loofia thienemanni;
(h) Globodera rostochiensis, Globodera pallida, Globodera tabacum of the family Heteroderidae, e.g. Globodera spp.; (Heterodera spp.), Heterodera avenae, Heterodera cruciferae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii;
(i) of the family Hoplolimidae, for example, Helicotylenchus spp., Helicotylenchus dihystera, Helicotylenchus multicinctus; Columbus (Hoplolaimus columbus), Hoplolaimus galeatus; Others, Rotylenchus robustus, Rotylenchus reniformis;
(j) Meloidogyne family (Meloidogynidae), for example, Meloidogyne spp. Meloidogyne javanica, Meloidogyne thamesi;
(k) of the family Nothotylenchidae, such as Nothotylenchus acris;
(l) Paratylenchidae, for example, Paratylenchus spp. Paratylenchus curvitatus, Paratylenchus elachistus;
(m) Platylenchus family (Pratylenchidae), for example, Pratylenchus spp. species, Platylenchus brachyurus, Pratylenchus coffeae, Pinnematode (Pratylenchus curvitatus) , Pratylenchus fallax, Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Platylenchus scribneri, Walnut Pratylenchus vulnus, Pratylenchus zeae; others, Nacobbus aberrans, Radopholus similis, Tylenchulus semipenetrans, Radopholus citrophilus ).

(2) Dorylaimida
(a) Longidoridae, e.g., Longidorus spp., Longidorus elongates; Xiphinema, Xiphinema americanum, Xiphinema brevicole (Xiphinema brevicolle), Grape Nematode (Xiphinema index), Xiphinema diversicaudatum (Xiphinema diversicaudatum).

(3) Triplonchida
(a) Trichodoridae family (Trichodoridae), for example, Trichodorus primitibus (Trichodorus primitibus), Nematode nematode (Paratrichodorus minor).

[Method of application/mixture]
The agricultural and horticultural fungicides or nematicides of the present invention are grains; vegetables; root vegetables; potatoes; fruit trees, tea, coffee, trees such as cacao; It is preferably used for

The agricultural and horticultural fungicide of the present invention can be applied to various parts of plants, such as leaves, stems, stems, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots and cuttings. . Nematicides can be applied to roots, tubers, root tubers, and the like. In addition, improved cultivars/varieties, cultivated cultivars, mutants, hybrids, and genetically modified organisms (GMO) of these plants can also be targeted.

The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. for the control of various diseases occurring in agricultural and horticultural crops including flowers, lawns, and pastures. can be done. Nematicides can be used in seed treatments, soil applications, and the like.

The agricultural and horticultural fungicide or nematicide of the present invention may contain ingredients other than the pyridazinone compound of the present invention. Other components include known carriers used for formulation. Examples of other components include conventionally known fungicides, insecticides/miticides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds, and the like. be able to. A synergistic effect may be produced by containing such other components.
Thus, one aspect of the present invention is an agricultural and horticultural fungicide containing one or more additional fungicides.

As a fungicide that can be mixed or used together with the agricultural and horticultural fungicide or nematicide of the present invention, it is described on the FRAC (Fungicide Resistance Action Committee) website (https://www.frac.info/) Compounds or agriculturally acceptable salts or derivatives thereof can be mentioned as preferred ones.
Specifically, compounds selected from the following group can be exemplified.

Fungicide:

(A) Agent acting on nucleic acid synthesis metabolism:
A1) RNA polymerase I inhibitors benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, ofurace.
A2) Adenosine deaminase inhibitors bupirimate, dimethirimol, ethirimol.
A3) DNA/RNA biosynthesis inhibitors hymexazole, octhilinone.
A4) DNA topoisomerase type II inhibitor oxolinic acid.

(B) agents acting on cytoskeleton and motor proteins:
B1)-B3) beta-tubulin polymerization inhibitors benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, ethaboxam, chlorfenazole, debacarb, trichlamide, zarilamid.
B4) cell division (point of action unknown) inhibitor pencycuron.
B5) Delocalization inhibitors of spectrin-like proteins fluopicolide, fluopimomide.
B6) Actin/myosin/fimbrin function inhibitors phenamacril, metrafenone, pyriofenone.

(C) Respiratory agents:
C1) Complex I: NADH oxidoreductase inhibitors diflumetorim, tolfenpyrad, fenazaquin.
C2) Complex II: succinate dehydrogenase inhibitors benodanil, flutolanil, mepronil, isofetamide, fluopyram, cyclobutrifluram, fenfuram , carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, inpyrfluxam, isopyrazam, penflufen, penthiopyrad, sedaxane, isoflucypram, pydiflumetofen, boscalid, pyraziflumide ( pyraziflumid, Flubeneteram, furmecyclox.
C3) Complex III: cytochrome bc1 (ubiquinol oxidase) Qo site (cyt b gene) inhibitors azoxystrobin, coumoxystrobin, enoxastrobin, fluphenoxystrobin ( flufenoxystrobin, picoxystrobin, pyraoxystrobin, mandestrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, kresoxim -methyl), trifloxystrobin, dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin ), fenamidone, pyribencarb, methyltetraprole.
C4) Complex III: Cytochrome bc1 (ubiquinone reductase) Qi site inhibitors cyazofamid, amisulbrom, fenpicoxamid, florylpicoxamid, methallylpicoxamide ( metarylpicoxamid).
C5) Uncoupling inhibitors of oxidative phosphorylation binapacryl, dinocap, meptyldinocap, fluazinam.
C6) Oxidative phosphorylation, inhibitors of ATP synthase Triphenyltin acetate, fentin chloride, triphenyltin hydroxide.
C7) ATP transport inhibitor silthiofam.
C8) Complex III: cytochrome bc1 (ubiquinone reductase) Qo site, stigmaterin-binding subsite inhibitor ametoctradin.

(D) Agents Affecting Amino Acid and Protein Synthesis:
D1) Methionine biosynthesis (cgs gene) inhibitors cyprodinil, mepanipyrim, pyrimethanil.
D2) Protein synthesis (ribosomal translation termination step) inhibitor blasticidin-S.
D3), D4) Protein synthesis (ribosome translation initiation step) inhibitors kasugamycin, kasugamycin hydrochloride, streptomycin.
D5) Protein synthesis (ribosomal polypeptide elongation step) inhibitor oxytetracycline.

(E) agents that affect signal transduction:
E1) signaling (mechanism of action unknown) inhibitors quinoxyfen, proquinazid.
E2) MAP/histidine kinase (os-2, HOG1) inhibitors fenpiclonil, fludioxonil in osmotic signaling.
E3) MAP/histidine kinase (os-1, Daf1) inhibitors in osmotic signaling chlozolinate, dimethachlone, iprodione, procymidone, vinclozolin.

(F) agents that affect lipid biosynthesis or transport/cell membrane structure or function:
F1) Dicarboximide fungicides F2) Phospholipid biosynthetic, methyltransferase inhibitors edifenphos, iprobenfos, pyrazophos, isoprothiolane.
F3) Cellular peroxidation inhibitors biphenyl, chloroneb, dichloran, quintozene, tecnazene, tolclofos-methyl, etridiazole.
F4) Cell membrane permeable, fatty acid inhibitors iodocarb, propamocarb, propamocarb hydrochloride, prothiocarb.
F5) carboxylic acid amide (CAA) fungicides F8) ergosterol binding inhibitor natamycin;
F9) Lipid homeostasis and transport/storage inhibitors oxathiapiprolin, fluoxapiprolin.

(G) Cell Membrane Sterol Biosynthesis Inhibitors G1) C14 Demethylase (erg11/cyp51) Inhibitors of Sterol Biosynthesis Triforine, Pyrifenox, Pyrisoxazole, Fenarimol, Nuarimol (nuarimol), imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol, bromuconazole , cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flu triafol (flutriafol), hexaconazole, imibenconazole, ipconazole, mefentrifluconazole, metconazole, myclobutanil, penconazole, propico propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, fluoxy Tioconazole (Fluoxytioconazole), fluconazole (furconazole), fluconazole-cis, diniconazole-M.
G2) Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) inhibitors in sterol biosynthesis aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph ), fenpropidin, piperalin, spiroxamine, buthiobate.
G3) 3-keto reductase (erg27) inhibitors fenhexamid and fenpyrazamine in C4 demethylation of sterol biosynthesis.
G4) Squalene epoxidase (erg1) inhibitors of sterol biosynthesis pyributicarb, naftifine, terbinafine.

(H) cell wall biosynthesis inhibitors:
H4) Chitin synthase inhibitors polyoxin, polyoxorim.
H5) Cellulose synthase inhibitors dimethomorph, flumorph, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate, mandipropamid.

(I) cell wall melanin synthesis inhibitor:
I1) Reductase inhibitors of melanin biosynthesis fthalide, pyroquilon, tricyclazole.
I2) Dehydratase inhibitors of melanin biosynthesis carpropamid, diclocymet, fenoxanil.
I3) Tolprocarb, a polyketide synthase inhibitor of melanin biosynthesis.

(P) Agents that act to induce resistance in host plants:
P01-P03) Agents involved in salicylate signaling: acibenzolar-S-methyl, probenazole, tiadinil, isotianil.
P04) Polysaccharide elicitor laminarin.
P05) Anthraquinone elicitor extract from Reynoutria sachalinensis.
P06) Microorganism Elicitor Bacillus mycoides isolate J, cell walls of Saccharomyces cerevisiae strain LAS117.
P07) phosphorous acid and salts such as fosetyl-Al, phosphorous acid and calcium phosphite, aluminum phosphite, sodium phosphite, disodium phosphonate ).
P08) Dichlobentiazox, an agent involved in salicylate signaling.

(U) Agents with unknown mechanisms of action:
cymoxanil, teclofthalam, triazoxide, flusulfamide, diclomezine, cyflufenamid, dodine, dodine free base, flutianil, ferimzone (ferimzone), tebufloquin, picarbutrazox, validamycin, bethoxazin, cyprofuram, flumetover, nitrothal-isopropyl, propamidine , ipflufenoquin, pyridaclomethyl, pyrapropoyne, aminopyrifen, ipfentrifluconazole, quinofumelin, dipymetitrone, cloinconazide (chloroinconazide), seboctylamine, Flumetylsulforim, Flufenoxadiazam.

(M) an agent having multisite contact activity:
Copper (different salts), basic copper sulfate, Bordeaux mixture, copper hydroxide, copper naphthenate, copper oxychloride oxychloride), copper sulfate, cuprous oxide, oxine-copper, sulfur, lime sulfur, amobam, ferbam, mancozeb (mancozeb), maneb, metiram, propineb, thiram, zinc thiazole, zineb, ziram, captan, captafol , folpet, chlorothalonil, dichlofluanid, tolylfluanid; guazatine, guazatine acetates, iminoctadine, iminoctadine triacetate , iminoctadine trialbesilate, anilazine, dithianon, chinomethionat/quinomethionate, fluoroimide, methasulfocarb, dazomet, cufraneb, mancopper, polycarbamate.

(BM) Biological/biological pesticides with multiple mechanisms of action:
a) Plant extracts Polypeptide (lectin), Phenols, Sesquiterpenes, Triterpenoids, Coumarins, Terpene Hydrocarbons ), terpene alcohols, terpene phenols, extract from the cotyledons of lupine plantlets, extract from Swinglea glutinosa, mint. extract from Melaleuca alternifolia (tea tree oil), plant oils (mixtures), eugenol, geraniol, thymol, α- Alpha-pinene, α-Terpinene, Alpha-Terpinol, Alpha-Terpinolene, Gamma-Terpinene, d-Limonene ), Orange Oil, Linalool, Menthol, ursolic acid, Oleanolic Acid, neem oil.
b) Microorganisms (microbial strains or their extracts or metabolites)
Trichoderma atroviride strain I-1237, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1, Trichoderma atroviride strain SKT-1 strain SKT-1), Trichoderma atroviride strain 77B;
Trichoderma asperellum strain T34, Trichoderma asperellum strain kd;
Trichoderma harzianum T-22 strain (Trichoderma harzianum strain T-22);
Trichoderma spp., such as Trichoderma virens strain G-41.
Gliocladium spp., such as Gliocladium catenulatum strain J1446.
Clonostachys spp., such as Clonostachys rosea strain CR-7.
Coniothyrium spp., such as Coniothyrium minitans strain CON/M/91-08.
Talaromyces spp., such as Talaromyces flavus strain SAY-Y-94-01;
Saccharomyces spp., such as Saccharomyces cerevisae strain LAS02.
Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain MBI600 Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens AT-332 strain (Bacillus amyloliquefaciens strain AT-332);
Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis strain HAI-0404; Bacillus simplex and other bacilli Bacillus spp.
Paenibacillus spp.
Burkholderia spp.
Fusarium spp.
Pseudomonas spp., such as Pseudomonas chlororaphis strain AFS009, Pseudomonas fluorescens, and Pseudomonas rhodesiae HAI-0804.
Streptomyces spp. such as Streptomyces griseovirides strain K61 and Streptomyces lydicus strain WYEC108.
Agrobacterium spp., such as Agrobacterium radiobacter.
Erwinia spp., such as non-pathogenic Erwinia carotovora subsp. carotovora.
Variovorax spp., such as Variovorax paradoxus.
Lactobacillus spp., such as Lactobacillus plantarum.
c) Other agents Yeast or its extract, β-glucan, chitin or chitosan or fragments thereof, β-aminobutyric acid, 2,6-dichloroisonicotinic acid, salicylic acid or derivatives thereof, algae extract, algae extract (hydrolyzed , jasmine flower extract, sodium alginate, oligosaccharides, trehalose, polysaccharides, lipids, lipopolysaccharides, fatty acids, glycolipids, glycoproteins, glycopeptides, proteins or peptides derived from plants and/or pathogenic microorganisms, ergosterol, etc. A substance that can be an elicitor of

(N) unclassified agents mineral oils, organic oils, inorganic salts, material of biological origin, Potassium bicarbonate, sodium bicarbonate ( Sodium hydrogen carbonate, Calcium carbonate, Calcium hydroxide, Potassium iodide, Potassium phosphonates, Chitosan hydrochloride, Urea.

As an insecticide / acaricide that can be mixed or used together with the agricultural and horticultural fungicide or nematicide of the present invention, IRAC (Insecticide Resistance Action Committee) HP (https://irac-online.org/) The compounds described, or their agriculturally acceptable salts or derivatives, etc. can be mentioned as preferred ones.
Specifically, compounds selected from the following group can be exemplified.

Insecticides and acaricides:
(1A) Acetylcholinesterase (AChE) inhibitor (carbamate):
Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarbboxim, Butoxycarbboxim, Carbaryl, Carbofuran, Carbosulfan ( Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb ( Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb, Aldoxycarb, Allyxycarb, Aminocarb (Aminocarb), Bufencarb, Cloethocarb, Fenothiocarb, Promecarb.

(1B) Acetylcholinesterase (AChE) inhibitors (organophosphorus):
Acephate, Azamethifos, Azinphos-ethyl, Azinphosmethyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/ DDVP, Dicrotophos, Dimethoate ( Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate ( Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylate, Isoxathion, Malathion , Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion , Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet , Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep ( Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorfon, Vamidothion, Bromophos-ethyl ( Bromophos-e, Cyanofenphos, Demeton-S-methylsulfone, Dialifos, Dichlofenthion, Dioxabenzofos, Etrimfos, Fensulfothion (Fensulfothion), Fonofos, Formothion, iodofenphos, Isazofos, Isocarbofos, Methacrifos, Phosphocarb, Pirimiphos-e, Propaphos, Prothoate, Sulprofos.

(2) GABAergic chloride ion (chloride ion) channel blockers:
Chlordane, Endosulfan, Ethiprole, Fipronil, Acetoprole, Camphechlor, Dienochlor, Heptachlor, Pyrafluprole, Pyriprole ( Pyriprole), Flufiprole.

(3A) Sodium channel modulators (pyrethroids):
Acrinathrin, Allethrin, d-cis-trans Allethrin, d-transAllethrin, Bifenthrin, Bioallethrin, Bioallethrin -S-Cyclopentenyl-isomer (Bioallethrin S-cyclopentenyl-isomer), Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, λ- Cyhalothrin (lambda-Cyhalothrin), gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin ), zeta-Cypermethrin, Cyphenothrin [(1R)-trans-isomers], Deltamethrin, Empentrin [(EZ)-(1R) -isomers] (Emphenthrin [(EZ)-(1R)-isomers] ), Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate ( Flucythrinate, Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(1R)-trans isomer] (Phenothrin [(1R)-trans-isomer] ), Prallethrin, Pyrethrins, Resmethrin ( Resmethrin), Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-isomers], Tralomethrin, Transfluthrin, κ-Bifenthrin, Biopermethrin, Chloroprallethrin, Dimefluthrin, Fenfluthrin, Fenpirithrin, Flufenprox, Heptaflu Heptafluthrin, Meperfluthrin, epsilon-Metofluthrin, Momfluorothrin, epsilon-Momfluorothrin, trans-Permethrin, Profluthrin , Protrifenbute, kappa-Tefluthrin, Terallethrin, Tetramethylfluthrin, Bioethanomethrin.

(3B) Sodium channel modulators (DDTs):
DDT, Methoxychlor.

(4) nicotinic acetylcholine receptor (nAChR) competitive modulators:
Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam, Nicotine, Sulfoxaflor, Flupyradifurone, Triflumezopyrim, Nithiazine, Dicloromezotiaz, Flupyrimin.

(5) Nicotinic Acetylcholine Receptor (nAChR) Allosteric Modulators:
Spinetoram, Spinosad.

(6) Glutamatergic chloride (chloride) channel (GluCl) allosteric modulators:
Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin, Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.

(7) juvenile hormone-like agents:
Hydroprene, Kinoprene, Methoprene, Fenoxycarb, Pyriproxifen, Diofenolan, Epofenonane, Triprene.

(8) Other non-specific (multi-site) inhibitors:
Alkyl halides such as methyl bromide, Chloropicrin, Sodium aluminum fluoride, Sulfuryl fluoride, Borax, Boric acid ( Boric acid), Disodium octaborate, Sodium borate, Sodium metaborate, Tartar emetic, Dazomet, Metam, Metam Potassium Salt (Metam Sodium), Metam Sodium Salt (Metam Potassium).

(9) String tone organ TRPV channel modulators:
Pymetrozine, Pyrifluquinazon, Afidopyropen.

(10) Mites growth inhibitor:
Clofentezine, Diflovidazin, Hexythiazox, Etoxazole.

(11) Microorganism-derived insect midgut lining-disrupting agent:
aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis, Bt crop proteins, Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1, Bacillus sphaericus.
Note) "Bt" stands for Bacillus thuringiensis, and "protein contained in Bt crops" refers to crops into which the gene for the toxin protein (Cry1Ab, etc.) produced by Bt (Bacillus thuringiensis) has been introduced. It is a protein produced within

(12) Mitochondrial ATP synthase inhibitor:
Diafenthiuron, Azocyclotin, Cyhexatin, Fenbutatin-oxide, Propargite, Tetradifon.

(13) Oxidative phosphorylation uncouplers that perturb the proton gradient:
Chlorfenapyr, DNOC (4,6-dinitro-o-cresol), Sulfluramid, Binapacryl, Dinobuton, Dinocap.

(14) Nicotinic Acetylcholine Receptor (nAChR) Channel Blockers:
Bensultap, Cartap hydrochloride, Thiocyclam, Thiosultap-sodium.

(15) Chitin biosynthesis inhibitor, type 0:
Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron ), Noviflumuron, Teflubenzuron, Triflumuron, Fluazuron.

(16) chitin biosynthesis inhibitor, type 1:
Buprofezin.

(17) molting inhibitor:
Cyromazine.

(18) molting hormone (ecdysone) receptor agonists:
Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.

(19) Octopamine receptor agonists:
Amitraz, Chlordimeform.

(20) mitochondrial electron transport chain complex III inhibitor:
Hydramethylnon, Acequinocyl, Fluacrypyrim, Bifenazate.

(21) mitochondrial electron transport chain complex I inhibitor (METI):
Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad, Rotenone.

(22) voltage-gated sodium channel blockers:
Indoxacarb, Metaflumizone.

(23) Acetyl-CoA carboxylase inhibitors:
Spirodiclofen, Spiromesifen, Spirotetramat, Spiropidion.

(24) mitochondrial electron transport chain complex IV inhibitor:
Aluminum phosphide (Al-phosphide), Calcium phosphide (Ca-phosphide), Zinc phosphide (Zn-phosphide), Phosphine, Calcium cyanide (Ca-cyanide), Sodium cyanide (Na-cyanide), Potassium cyanide (K-cyanide).

(25) mitochondrial electron transport chain complex II inhibitor:
Cyenopyrafen, Cyflumetofen, Pyflubumide.

(26) ryanodine receptor modulators:
Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Flubendiamide, Cyhalodiamide, Tetrachlorantraniliprole, Tetraniliprole ( Tetraniliprole).

(27) Chordotome modulator Target site unspecified:
Flonicamid.

(28) GABAergic chloride (chloride) channel allosteric modulators:
Broflanilide, Fluxametamide, Isocycloseram, Afoxolaner, Fluralaner, Lotilaner, Sarolaner.

(29) Agents with unknown mechanism of action (UN):
Azadirachtin, Benzoximate, Bromopropylate, Chinomethionat/Quinomethionate, Dicofol, Lime sulfur, Mancozeb, Pyridalyl, Sulfur.

(30) Other insecticides, acaricides:
Acinonapyr, Amidoflumet, Benzomate, Benzpyrimoxan, Chlorobenzilate, Dicyclanil, Fenoxacrim, Fentrifanil, Flometoquin, Flubenzimine, Flufenzine, Fluhexafon, Fluopyram, Metaflumizone, Metoxadiazone, Oxazosulfyl, Tetrasul, Triarasen ( Triarathene), Tyclopyrazoflor.

Plant growth regulators can also be mixed. Specific examples of the plant growth regulator that can be mixed include compounds selected from the following group.
abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenurone ( chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N - N-acetyl aminoethoxyvinyl glycine (aviglycine), aminooxyacetate, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop (cloprop), 2,4-D, MCPB, indole-3-butyrate, dichlorprop, phenothiol, 1-naphthyl acetamide, eticlozate (ethychlozate), cloxyfonac, maleic acid hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate salicylate), (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol ((+ )-deoxystrigol), (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid (4-oxo -4-(2-phen ylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid, daminozide.

Anthelmintics can also be mixed. As an antiparasitic agent that can be mixed, specifically, compounds selected from the following group can be exemplified.
Anthelmintic:
(a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimine, thiophanate; thiabendazole, cambendazole;
(b) Salicylanilides: Closantel, Oxyclozanide, Rafoxanide, Niclosamide;
(c) substituted phenolics: nitroxynil, nitroscanate;
(d) pyrimidine series: pyrantel, morantel;
(e) imidazothiazoles: levamisole, tetramisole;
(f) tetrahydropyrimidines: praziquantel, epsiprantel;
(g) Other anthelmintics: cyclodiene, liania, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel; thiacetarsamide, melarsomine, arsenamide.

[Formulation formulation]
The agricultural and horticultural fungicide or nematicide of the present invention includes the pyridazinone compound of the present invention, other active ingredients and agricultural and horticulturally acceptable auxiliary ingredients for formulation (e.g., inorganic carriers, organic carriers, surfactants, solvents, etc.) can be added.
The agricultural and horticultural fungicide or nematicide of the present invention is not particularly limited by its dosage form. For example, dosage forms such as wettable powders, emulsions, powders, granules, aqueous solutions, suspensions, wettable powders, and tablets can be mentioned. The preparation method for the formulation is not particularly limited, and a known preparation method can be adopted depending on the dosage form.
Some formulation examples are shown below. The formulation shown below is merely an example, and can be modified within the scope of the present invention, and the present invention is not limited by the following formulation examples. "Parts" means "parts by weight" unless otherwise specified.

(Formulation Example 1: wettable powder)
40 parts of the pyridazinone compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder containing 40% of the active ingredient.
(Formulation Example 2: Emulsion)
30 parts of the pyridazinone compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide and 7 parts of polyoxyethylene alkylallyl ether are mixed and dissolved to obtain an emulsion containing 30% active ingredient.
(Formulation Example 3: Granules)
5 parts of the pyridazinone compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite and 7 parts of sodium alkyl sulfate are uniformly mixed, finely pulverized, and then granulated to a particle diameter of 0.5 to 1.0 mm. to obtain 5% active ingredient granules.
(Formulation Example 4: Granules)
5 parts of the pyridazinone compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt and 1 part of potassium phosphate were uniformly mixed and pulverized. Water is added to this and the mixture is thoroughly kneaded, then granulated and dried to obtain granules containing 5% of the active ingredient.
(Formulation Example 5: Suspension agent)
10 parts of the pyridazinone compound of the present invention, 4 parts of polyoxyethylene alkylallyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water are mixed to reduce the particle size to 3 microns or less. Wet pulverize until it becomes a suspension of 10% of the active ingredient.
(Formulation Example 6: Granule wettable powder)
40 parts of the pyridazinone compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzenesulfonate, 8 parts of sodium ligninsulfonate and 5 parts of formaldehyde condensate of sodium alkylbenzenesulfonate are uniformly mixed. After pulverizing it finely, add an appropriate amount of water and knead it into clay. The clay is granulated and then dried to obtain water dispersible granules containing 40% active ingredient.

[Medical and veterinary (veterinary) antifungal agents]
The pyridazinone compound of the present invention can be used as a prophylactic or therapeutic agent for controlling harmful pathogens, particularly fungi, that infect humans or animals.
The medical/veterinary antifungal agent of the present invention contains at least one selected from compound (I) and salts thereof as an active ingredient. The amount of compound (I) or a salt thereof contained in the medical antifungal agent of the present invention is not particularly limited as long as the antifungal effect is exhibited.

The term "animal" as used herein refers to pets, livestock and poultry, animals raised in zoos and aquariums, captured wild animals, and vertebrates such as research and experimental animals ( means ra t a).

Examples include the following animals, but specific examples of animals are not limited to these.
sheep, goat, pig, horse, cow, buffalo, donkey, mule, camel, llama, alpaca, wild boar, reindeer, deer, mink, elephant, bear, kangaroo, fox, dog, cat, squirrel, rabbit, mouse, rat, Mammals such as guinea pigs, hamsters, monkeys and ferrets.
Birds such as pigeons, parakeets, parrots, sparrows, marigolds, canaries, chickens, ducks, turkeys, ducks, pheasants, peacocks, ostriches, swans, sparrows, quail, owls, eagles, hawks, and cormorants.
Reptiles such as chameleons, iguanas, lizards, snakes, turtles, crocodiles and geckos.
Amphibians such as frogs and newts.
Fish such as carp, goldfish, killifish, tropical fish, yellowtail, yellowtail, sea bream, amberjack, salmon, mackerel, sea bass, longtooth grouper, tuna, horse mackerel, flounder, and pufferfish.

Examples of fungi (molds) are shown below as pathogenic bacteria to which the medical and veterinary antifungal agent of the present invention can be applied. However, specific examples are not limited to these.
For example, the genus Absidia, such as absidia corymbifera; the genus Acremonium; the genus Alternaria, such as Alternaria alternata; the genus Aspergillus, such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, Aspergillus parasiticus, and Aspergillus terreus; ; Blumeria genus such as Blumeria graminis; Candida genus such as Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, Candida tropicalis; Cladosporium genus such as Cladosporium cladosporoides and Cladosporium herbarium; Cryptococcus genera such as Cryptococcus neoformans; Curvularia genera such as Curvularia lunata; Encephalitozoon genera such as Encephalitozoon cuniculi; Epicoccum genera such as Epicoccum nigrum; Fusarium genera, such as graminarium, Fusarium solani, and Fusarium sporotrichoides; Fonsecaea genera, such as Fonsecaea monophora; Histoplasma genera, such as Histoplasma capsulatum; Leptos, such as Leptosphaeria nodorum Genus phaeria; genus Malassezia such as Malassezia globosa; genus Microsporum such as Microsporum canis; genus Mycosphaerella such as Mycosphaerella graminicola; genus Neurospora; Pneumocystis genus such as Pneumocystis jirovecii; Pyricularia genus such as Pyricularia oryzae; Pythium genus such as Pythium ultimum; Puccinia genus such as Puccinia coronata and Puccinia graminis; Rhizoctonia genus such as Rhizoctonia solani; Scedosporium genera such as Fusarium apiospermum and Scedosporium prolificans; Scopulariopsis genera such as Scopulariopsis brevicaulis; Sporothrix genera such as Sporothrix schenckii; Talaromyces genera such as Talaromyces marneffei; genus Trichosporon, such as Trichosporon asahii and Trichosporon beigelii; genus Ustilago;
Among these, the antifungal agent of the present invention is suitable for Aspergillus, Trichophyton or Candida, and particularly suitable for Aspergillus fumigatus or Trichophyton tonsurans.

Examples of mycosis are shown below as infectious diseases to which the medical and veterinary antifungal agent of the present invention can be applied. However, specific examples are not limited to these.

The medical/veterinary antifungal agent of the present invention can be applied to both systemic fungal infections and superficial fungal infections. Specific examples of fungal infections include Aspergillus diseases such as pulmonary aspergillosis, systemic aspergillosis (which is more likely to occur in immunosuppressed patients such as bone marrow recipients or AIDS patients), Candida diseases such as systemic candidiasis ( Candida disease, Cryptococcus meningitis, rhinocerebral mucomycosis, pulmonary mucormycosis, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, robomycosis, Keratomycosis, sporotrichosis, chromoblastomycosis, chromomycosis, pheophyphomycosis, zygomycosis, cryptococcosis, disseminated sporotrichosis, ring worm, tinea capitis, tinea corporis , tinea pedis (athlete's foot), tinea pedis (athlete's foot), tinea unguium (athlete's foot), candidiasis of the skin, mouth, or vagina, malassechiosis, chronic mucocutaneous candidiasis, Pneumocystis pneumoniae, and penicilliosis of the Marnefei type. be done.
In addition, the antifungal agent of the present invention can also be applied to allergic diseases caused by fungi, such as allergic bronchopulmonary asthma (ABPA); asthma, rhinosinusitis, or sinusitis. be.

The medical/veterinary antifungal agent of the present invention can contain pharmaceutically acceptable additives. Additives are not particularly limited as long as they are used in known medical drugs. They are of course sterile and non-pyrogenic. In addition, the additive can be appropriately selected according to the dosage form and administration method of the antifungal agent.

The dosage form that the medical/veterinary antifungal agent of the present invention can take is not particularly limited. , emulsions, suspensions, solutions, drops (Pour-on), spot-on, etc.; semi-solid preparations such as ointments, gels, etc.; aerosols, vapors, etc. Gaseous agents; nanoparticle formulations and the like can be mentioned.
Administration of the medical antifungal agent of the present invention can be performed by known methods. Examples of administration methods include subcutaneous, intravenous, intramuscular, intrasternal injection (injection); insertion into the anus, vagina, etc.; oral administration such as oral administration; nasal administration such as inhalation.

In the case of oral solid formulations, additives that can be used in the medical and veterinary antifungal agents of the present invention include solubilizers such as cyclodextrins or modified cyclodextrins; lactose, dextrose, sucrose, cellulose, cornstarch or Diluents such as potato starch; Lubricants such as silica, talc, stearic acid, magnesium or calcium stearate, polyethylene glycol; Binding agents such as starch, arabic gums, gelatin, methylcellulose, carboxymethylcellulose or polyvinylpyrrolidone. agents; disaggregating agents such as starch, alginic acid, alginates or sodium starch glycolate; effervescing mixtures; dyes; sweeteners; Alternatively, non-toxic and pharmacologically inactive substances generally used in pharmaceutical formulations can be used. These additives can be incorporated into the medical antifungal agent of the present invention by known methods such as mixing, granulation, tableting, sugar coating, or film coating.

In the case of liquid formulations for oral administration, additives that can be used in the medical and veterinary antifungal agents of the present invention include solubilizers such as cyclodextrins or modified cyclodextrins, saccharose, glycerin, mannitol, sorbitol, natural gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, polyvinyl alcohol, and the like.

In the case of a liquid preparation for intramuscular injection, the additives that can be used in the medical and veterinary antifungal agent of the present invention include sterilized water, olive oil, ethyl oleate, glycols such as propylene glycol, cyclodextrin, and modified cyclodextrins. Dissolution aids such as dextrin can be used. Furthermore, an appropriate amount of lidocaine hydrochloride can be included as necessary.

In the case of a liquid preparation for intravenous injection, examples of additives that can be used in the medical or veterinary antifungal agent of the present invention include carriers such as sterile water; solubilizers such as cyclodextrins and modified cyclodextrins. can. They can also be included in the form of sterile isotonic saline solutions.

The amount of compound (I) or a salt thereof contained in the medical or veterinary antifungal agent of the present invention is preferably 85% by weight or less, more preferably 50% by weight or less, based on the weight of the antifungal agent. .
The dose of the medical/veterinary antifungal agent of the present invention can be appropriately selected according to the administration method, the type of fungi infected, the patient's age, body weight, symptoms, and the like. For example, for adults, in the case of oral or parenteral (injection, infusion, etc.) administration, 0.1 to 100 mg/kg-body weight can be administered once or several times a day.
In addition, the medical and veterinary antifungal agents of the present invention can be used in combination with drugs other than pyridazinone compounds.

Synthesis examples are shown below to describe the present invention more specifically. However, the present invention is in no way limited by the following synthesis examples.
[Example 1]
(E)-2-(5-(1-(isopropoxyimino)ethyl-3-(2-methoxyphenethyl)-6-oxopyridazin-1(6H)-yl)-N-isopropylpropanamide [(E) Synthesis of -2-(5-(1-(isopropoxyimino)ethyl)-3-(2-methoxyphenethyl)-6-oxopyridazin-1(6H)-yl)-N-isopropylpropanamide] (Step 1)
Synthesis of methyl 3-methoxy-6-((2-methoxyphenyl)ethynyl)pyridazine-4-carboxylate

Methyl 6-chloro-3-methoxypyridazine-4-carboxylate (2.65 g) was dissolved in dimethylformamide (90 ml), trimethylamine (150 ml). To this, 1-ethynyl-2-methoxybenzene (1.90 g), copper (I) iodide (0.42 g) and bis(triphenylphosphine) palladium (II) dichloride (1.34 g) were added and the reaction vessel was replaced with nitrogen, and then stirred at 70° C. for 1 hour.
A saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 1.47 g of the desired product (yield 38%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.96 (1H, s), 7.57 (1H, q), 7.38-7.36 (1H, m), 6.99-6.92 (2H, m), 4.28 (3H, s ), 3.96 (3H, s), 3.93 (3H, s).

(Step 2)
Synthesis of methyl 3-methoxy-6-(2-methoxyphenethyl)pyridazine-4-carboxylate

Methyl 3-methoxy-6-((2-methoxyphenyl)ethynyl)pyridazine-4-carboxylate (1.60g) was dissolved in methanol (54ml) and palladium hydroxide (0.16g) was added. After purging the reaction vessel with hydrogen, the mixture was stirred overnight at room temperature.
The reaction solution was filtered through celite, the filtrate was concentrated under reduced pressure, and the obtained residue (1.59 g) was used as it was in the next step.

(Step 3)
Synthesis of 3-methoxy-6-(2-methoxyphenethyl)pyridazine-4-carboxylic acid

Methyl 3-methoxy-6-(2-methoxyphenethyl)pyridazine-4-carboxylate (1.59g) was dissolved in tetrahydrofuran (9ml), water (7ml) and lithium hydroxide monohydrate (0.34g). was added. After stirring this at room temperature for 1 hour, water and ethyl acetate were added and extracted to the reaction liquid.
1N Hydrochloric acid was added to the resulting aqueous layer under ice-cooling, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue (1.24 g) was directly used in the next step.

(Step 4)
Synthesis of N,3-dimethoxy-6-(2-methoxyphenethyl)-N-methylpyridazine-4-carboxamide [N,3-dimethoxy-6-(2-methoxyphenethyl)-N-methylpyridazine-4-carboxamide]

3-Methoxy-6-(2-methoxyphenethyl)pyridazine-4-carboxylic acid (1.24 g) was dissolved in methylene chloride (20 ml). To this was added N,O-dimethylhydroxylamine hydrochloride (0.50 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.06 g), 1-hydroxybenzotriazole monohydrate (0 .07 g) and triethylamine (1.8 ml) were added and stirred overnight at room temperature.
Water was poured into the reaction solution and extracted with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 1.15 g of the desired product (yield 65%, 3 steps).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.21-7.16 (1H, m), 7.11-7.09 (2H, m), 6.86-6.83 (2H, m), 4.16 (3H, s), 3.82 (3H , s), 3.46 (3H, s), 3.35 (3H, s) 3.22-3.05 (4H, m).

(Step 5)
1-(3-methoxy-6-(2-methoxyphenethyl)pyridazin-4-yl)ethan-1-one [1-(3-methoxy-6-(2-methoxyphenethyl)-pyridazine-4-yl)ethan- 1-one] synthesis

N,3-dimethoxy-6-(2-methoxyphenethyl)-N-methylpyridazine-4-carboxamide (0.25 g) was dissolved in anhydrous tetrahydrofuran (2.5 ml), the reaction solution was purged with nitrogen, and then- Cooled to 10°C. A 1.0 M methylmagnesium bromide tetrohydrofuran solution (1.1 ml) was added thereto, and the mixture was stirred at -10°C for 1 hour.
The reaction solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue (0.19 g) was directly used in the next step.

(Step 6)
1-(3-methoxy-6-(2-methoxyphenethyl)pyridazin-4-yl)ethan-1-one O-isopropyloxime [1-(3-methoxy-6-(2-methoxyphenethyl)-pyridazine-4- Synthesis of yl)ethan-1-one O-isopropyl oxime]

1-(3-Methoxy-6-(2-methoxyphenethyl)pyridazin-4-yl)ethan-1-one (0.19 g) was dissolved in ethanol (4.5 ml) and chloroform (4.5 ml). O-Isopropylhydroxylamine hydrochloride (0.10 g) and pyridine (0.07 ml) were added thereto, and the mixture was stirred overnight at room temperature.
The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.25 g of the desired product (yield 96%, two steps).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.21-6.94 (m, 3H), 6.89-6.84 (m, 2H), 4.48-4.29 (1H, m), 4.15-4.09 (3H, m), 3.82 (3H, s), 3.19-3.04 (4H, m), 2.15-2.09 (3H, m), 1.31-1.13 (6H, m).

(Step 7)
(E)-4-(1-(isopropoxyimino)ethyl)-6-(2-methoxyphenethyl)pyridazin-3(2H)-one [(E)-4-(1-(isopropoxyimino)ethyl)-6 Synthesis of -(2-methoxyphenethyl)-pyridazin-3(2H)-one]

1-(3-Methoxy-6-(2-methoxyphenethyl)pyridazin-4-yl)ethan-1-one O-isopropyloxime (0.12 g) was dissolved in dioxane (7 ml). 12N Hydrochloric acid (0.18 ml) was added thereto, and the mixture was stirred at 60°C overnight.
A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue (0.12 g) was used as such for the next step.

(Step 8)
(E)-2-(5-(1-(isopropoxyimino)ethyl-3-(2-methoxyphenethyl)-6-oxopyridazin-1(6H)-yl)-N-isopropylpropanamide [(E) Synthesis of -2-(5-(1-(isopropoxyimino)ethyl)-3-(2-methoxyphenethyl)-6-oxopyridazin-1(6H)-yl)-N-isopropylpropanamide]

(E)-4-(1-(isopropoxyimino)ethyl)-6-(2-methoxyphenethyl)pyridazin-3(2H)-one (0.12 g) dissolved in N,N-dimethylformamide (3 ml) let me 2-Bromo-N-isopropylpropanamide (0.08 g) and potassium carbonate (0.10 g) were added thereto, and the mixture was stirred overnight at room temperature.
A saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.15 g of the desired product (yield 97%, two steps).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.21-7.19 (1H, m), 7.16 (1H, s), 7.10 (1H, q), 6.88-6.83 (2H, m), 6.13 (1H, d ), 5.53 (1H, q), 4.48-4.38 (1H, m), 4.07-3.98 (1H, m), 3.80 (3H, s), 3.00-2.88 (4H, m), 2.19 (3H, s), 1.56 (3H, d), 1.29 (6H, d), 1.10 (6H, q).

[Example 2]
(S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-3-((2-methoxybenzyl)oxy)-6-oxopyridazin-1(6H)-yl)- 3-Methylbutan-2-yl)isobutyramide [(S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-3-((2-methoxybenzyl)oxy)-6-oxopyridazin-1 (6H)-yl)-3-methylbutan-2-yl)isobutyramide] (Step 1)
1-(6-chloro-3-methoxypyridazin-4-yl)ethan-1-one O-isopropyl oxime ] synthesis

1-(6-Chloro-3-methoxypyridazin-4-yl)ethan-1-one (1.21 g) was dissolved in ethanol (30 ml) and chloroform (30 ml). To this was added O-isopropylhydroxylamine hydrochloride (0.87 g) and stirred overnight at room temperature.
The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.88 g of the desired product (yield 56%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.44-7.21 (1H, m), 4.50-4.29 (1H, m), 4.19-4.13 (3H, m), 2.20-2.14 (3H, m), 1.36 -1.15 (6H, m).

(Step 2)
(E)-1-(6-chloro-3-hydroxypyridazin-4-yl)ethan-1-one O-isopropyloxime [(E)-1-(6-chloro-3-hydroxypyridazin-4-yl)ethan -1-one O-isopropyl oxime]

1-(6-Chloro-3-methoxypyridazin-4-yl)ethan-1-one O-isopropyloxime (0.45 g) was dissolved in N,N-dimethylformamide (8 ml). Paratoluenesulfonic acid monohydrate (1.76 g) and lithium chloride (0.39 g) were added thereto, and the mixture was stirred at 70° C. for 2 hours in an oil bath.
Then, after cooling to room temperature, water and saturated aqueous sodium bicarbonate were added, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was dried with anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the resulting crude product was used as such for the next step.

(Step 3)
Tert-Butyl (S,E)-(1-(3-chloro-5-(1-isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl) Carbamate [tert-butyl (S,E)-(1-(3-chloro-5-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl) synthesis of carbamate]

The crude product obtained in step 2 was dissolved in N,N-dimethylformamide (8 ml). (S)-2-((tert-Butoxycarbonyl)amino)-3-methylbutyl methanesulfonate (1.56 g) and cesium carbonate (3.01 g) were added thereto, and the mixture was stirred in an oil bath at 70°C for 30 minutes. did.
After cooling to room temperature, water and saturated ammonium chloride aqueous solution were added, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was dried with anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to give 0.60 g of the desired product (yield 78%, two steps). Obtained.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.29 (1H, s), 4.69 (1H, d), 4.49-4.38 (1H, m), 4.24-3.94 (3H, m), 2.22 (3H, s ), 1.97-1.77 (1H, m), 1.34 (9H, s), 1.30 (6H, d), 1.01 (6H, dd).

(Step 4)
(S,E)-2-(2-amino-3-methylbutyl)-6-chloro-4-(1-(isopropoxyimino)ethyl)pyridazin-3(2H)-one hydrochloride [(S,E) -2-(2-amino-3-methylbutyl)-6-chloro-4-(1-(isopropoxyimino)ethyl)pyridazin-3(2H)-one hydrogen chloride salt]

Tert-Butyl (S,E)-(1-(3-chloro-5-(1-isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl) Carbamate (0.26 g) was dissolved in 1,4-dioxane (2 ml). A 4M hydrochloric acid-dioxane solution (6 ml) was slowly added thereto, and the mixture was allowed to stand overnight at room temperature. After that, the reaction solution was concentrated under reduced pressure, and the obtained crude product was directly used in the next step.

(Step 5)
(S,E)-N-(1-(3-chloro-5-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl) Isobutyramide [(S,E)-N-(1-(3-chloro-5-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl) synthesis of isobutyramide]

The crude product obtained in step 4 was dissolved in dichloromethane (3 ml). Under ice-cooling, triethylamine (0.25 g) and isobutyryl chloride (0.10 g) were sequentially added, and the mixture was stirred at room temperature for 30 minutes.
Under ice-cooling, saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with dichloromethane. The resulting dichloromethane layer was dried over anhydrous magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.18 g of the desired product (yield 75%, two steps).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.30 (1H, s), 5.78 (1H, d), 4.49-4.38 (1H, m), 4.36-4.27 (2H, m), 4.15-4.01 (1H , m), 2.33-2.22 (1H, m), 2.20 (3H, s), 1.98-1.84 (1H, m), 1.32-1.24 (6H, m), 1.09 (3H, d), 1.04 (3H, d ), 1.01 (6H, dd).

(Step 6)
(S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-3-((2-methoxybenzyl)oxy)-6-oxopyridazin-1(6H)-yl)- 3-Methylbutan-2-yl)isobutyramide [(S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-3-((2-methoxybenzyl)oxy)-6-oxopyridazin-1 (6H)-yl)-3-methylbutan-2-yl)isobutyramide]

(S,E)-N-(1-(3-chloro-5-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl) Isobutyramide (0.050 g) was dissolved in 1,4-dioxane (2 ml). 2-Methoxybenzyl alcohol (0.040 g), sodium t-butoxy (0.015 g), [(2-di-tert-butylphosphino-3,6-dimethoxy-2',4',6'-Triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonic acid (0.003 g) was added, and the reaction vessel was flushed with nitrogen. Replaced under atmosphere. After that, the mixture was stirred at 100° C. for 1 hour in an oil bath.
Water and saturated aqueous ammonium chloride solution were added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was dried with anhydrous magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.016 g of the desired product (yield 25%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.42 (1H, dd), 7.36 (1H, dt), 7.08 (1H, s), 7.00 (1H, dt), 6.93 (1H, d), 6.21 ( 1H, d), 5.27 (2H, q), 4.62 (1H, dd), 4.45-4.27 (2H, m), 3.89 (3H, s), 3.79 (1H, dd), 2.33-2.22 (1H, m) , 2.19 (3H, s), 1.99-1.88 (1H, m), 1.27 (6H, dd), 1.09 (3H, d), 1.03 (3H, d), 1.01 (6H, d).

Table 1 shows some of the pyridazinone compounds of the present invention produced in the same manner as in the above Examples. The table also shows the melting point (°C) or physical properties of each compound as physical properties.

For some of the compounds in the table, the retention time in liquid chromatography mass spectrometry (LCMS) is shown.

Analysis conditions are shown below.
Waters CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 µm), temperature 40°C and flow rate 0.6 mL/min, 2 µL injection, mobile phase (A) water containing 0.1% formic acid, Mobile phase (B) was used with acetonitrile and retention times are expressed in minutes (minutes). (I) Electrophoresis was performed on ACQUITY UPLC H-Class (Waters) using an ACQUITY UPLC photodiode array (PDA) eλ detector (Waters) and an ACQUITY QDa detector (in positive and negative ion electrospray mode, UV PDA). Detection, manufactured by Waters), the concentration of the mobile phase (B) is increased from 30% by mass to 95% by mass with a linear gradient of 1.5 minutes, and (II) is maintained at 95% by mass for 0.5 minutes, (III) Immediately lowered to 30% by weight (B) and (IV) maintained at 30% by weight for 0.50 minutes.

Table 3 shows some of the pyridazinone compounds of the present invention produced in the same manner as in the above examples. The table also shows the melting point (°C) or physical properties of each compound as physical properties. Some compounds were also shown to be isomeric mixtures.

Retention times in liquid chromatography mass spectrometry (LCMS) are given for some of the compounds in the table.
Analysis conditions for liquid chromatography mass spectrometry (LCMS) are shown below.
Waters CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 µm), temperature 40°C and flow rate 0.6 mL/min, 2 µL injection, mobile phase (A) water containing 0.1% formic acid, Mobile phase (B) was used with acetonitrile and retention times are expressed in minutes (minutes).
(I) Electrophoresis was performed on ACQUITY UPLC H-Class (Waters) using an ACQUITY UPLC photodiode array (PDA) eλ detector (Waters) and an ACQUITY QDa detector (in positive and negative ion electrospray mode, UV PDA). Detection, manufactured by Waters Co., Ltd.), and Method (A) or Method (B) shown below was used.
Method (A):
The concentration of the mobile phase (B) was maintained at 30 wt% for 0.15 min, then increased linearly from 30 wt% to 95 wt% for 1.35 min, and (II) maintained at 95 wt% for 0.5 min. (III) immediately lowered to 30% by weight (B) and (IV) maintained at 30% by weight for 0.50 minutes.
Method (B):
The concentration of the mobile phase (B) was maintained at 30 wt% for 0.15 min, then increased linearly from 30 wt% to 95 wt% in 0.85 min, and (II) maintained at 95 wt% for 1.0 min. (III) immediately lowered to 30% by weight (B) and (IV) maintained at 30% by weight for 0.50 minutes.

Table 5 shows some of the pyridazinone compounds of the present invention produced in the same manner as in the above examples. The table also shows the melting point (°C) or physical properties of each compound as physical properties. Some compounds were also shown to be isomeric mixtures.

Table 6 shows retention times in liquid chromatography mass spectrometry (LCMS) for some of the compounds in the table.
The analysis conditions for liquid chromatography-mass spectrometry (LCMS) were Method (A) mentioned above and Method (C) shown below.
Method (C):
Waters Alliance e2695 separation module as HPLC system, SQ Detector 2 (in atmospheric pressure chemical ionization mode, PDA detection, Waters) as single quadrupole MS detector (LC/MS), 2998 PDA Photodiode as HPLC/UHPLC detector An Array Detector (manufactured by Waters) was used, XBridge BEH C18 (manufactured by Waters, 2.1 x 50 mm, 2.5 µm) was set as a column, and the temperature was set to 40°C. Water containing 0.1% formic acid was used as the mobile phase (A), and acetonitrile was used as the mobile phase (B). The retention time (minutes) of the sample was measured at a sample injection volume of 6 μL.
The column inlet concentration of the mobile phase (B) was maintained at 30% by mass for 0.3 minutes from the time of sample injection, and then increased at a constant rate from 30% by mass to 95% by mass over 1.7 minutes to 95% by mass. % and maintained for 1.5 minutes, then abruptly decreased to 30% by weight and maintained at 30% by weight for 2.5 minutes.

Table 7 shows some of the pyridazinone compounds of the present invention produced in the same manner as in the above examples. For some compounds in the table, their physical properties are also shown. Some compounds were also shown to be isomeric mixtures.

Table 8 shows retention times in liquid chromatography-mass spectrometry (LCMS) for some of the compounds in the table.
Method (A) mentioned above was used as the analysis conditions for liquid chromatography-mass spectrometry (LCMS).

In addition, Table 9 shows some of the compounds that can be production intermediates in preparing the pyridazinone compound of the present invention. The table also shows the melting point (° C.) as a physical property of each compound.

[Biological test]
The following test examples demonstrate that the pyridazinone compound of the present invention is useful as an active ingredient in agricultural and horticultural fungicides.
(Preparation of test emulsion)
5 parts by weight of the pyridazinone compound of the present invention, 93.5 parts by weight of N,N-dimethylformamide, and 1.5 parts by weight of polyoxyethylene sorbitan monolaurate (TWEEN (registered trademark) 20) are mixed and dissolved, An emulsion (I) with 5% active ingredient was obtained.

The control value was calculated using the following formula.

[Number 1]
Control value (%) = 100-{lesion area ratio in treated area / lesion area ratio in untreated area} × 100

(Test Example 1) Apple scab control test Water was added to the emulsion (I) so that the concentration of the pyridazinone compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on apple seedlings (variety “Orin”, 3-4 leaf stage) cultivated in pots for raising seedlings. After air-drying, conidia of Venturia inaequalis were inoculated (treated area). As a control, apple seedlings not sprayed with the drug solution were similarly inoculated (untreated group). They were placed in a moist chamber at 20°C with alternating light and dark cycles every 12 hours.
Two weeks after the inoculation, the leaves of the young apple seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.
B-1, B-2, B-3, B-4, B-5, B-6, B-7, B-8, B-10, B-11, B-12, B-13, B- 14, B-15, B-16, B-17, B-18, B-19, B-20, B-21, B-22, B-23, B-24, B-25, B-26, B-27, B-28, B-29, B-30, B-31, B-33, B-34, B-36, B-37, B-38, B-39, B-40, B- 41, B-42, B-43, B-44, B-45, B-46, B-47, B-48, B-49, C-16, C-17, C-18, and C-19 The apple scab control test was conducted for the compound of the compound of . All compounds showed a control value of 75% or more.

(Test Example 2) Cucumber gray mold control test Water was added to the emulsion (I) so that the concentration of the pyridazinone compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on cucumber seedlings (cultivar “Jibori” type, cotyledon stage) cultivated in pots for raising seedlings. After air-drying, a suspension of conidia of cucumber Botrytis cinerea was dropped and inoculated (treated area). As a control, cucumber seedlings not sprayed with the drug solution were inoculated dropwise in the same manner as above (untreated group). They were placed in a moist chamber at 20°C.
After 4 days from the inoculation, the leaves of the cucumber seedlings were visually observed, the lesion area ratio was determined, and the preventive value was calculated.
B-2, B-4, B-5, B-10, B-11, B-17, B-33, B-36, B-37, B-39, B-40, B-47, C- Compounds 16 and C-17 were tested for control of cucumber gray mold. A control value of 75% or more was shown.

(Test Example 3) Wheat powdery mildew control test Water was added to the emulsion (I) so that the concentration of the pyridazinone compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on wheat seedlings (variety “Chihoku”, 1-2 leaf stage) cultivated in nursery pots. After air-drying, conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were sprinkled and inoculated (treated group). As a control, wheat seedlings not sprayed with the drug solution were inoculated in the same manner as above (untreated group). They were placed in a greenhouse at 20°C.
After 6 days from the inoculation, the leaves of the seedlings of wheat were visually observed to determine the lesion area ratio, and the control value was calculated.
B-5, B-6, B-8, B-9, B-10, B-11, B-12, B-13, B-14, B-15, B-16, B-17, B- 18, B-19, B-20, B-21, B-22, B-23, B-24, B-25, B-26, B-27, B-28, B-33, B-34, B-36, B-37, B-38, B-39, B-40, B-41, B-42, B-43, B-44, B-45, B-46, B-47, B- Compounds 48, C-17 and D-3 were tested against wheat powdery mildew. All compounds showed a control value of 75% or more.

(Test Example 4) Wheat leaf rust control test Water was added to the emulsion (I) so that the concentration of the pyridazinone compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on wheat seedlings (variety “Nourin No. 61”, 1-2 leaf stage) cultivated in nursery pots. After air-drying, uredospores of wheat leaf rust fungus (Puccinia recondita) were sprinkled on the wheat seedlings to which the chemical solution had been sprayed and inoculated (treated area). As a control, wheat seedlings not sprayed with the drug solution were inoculated in the same manner as above (untreated group). They were placed in a greenhouse at 20°C.
On the day 12 days after inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.
Compounds B-4, B-5, B-36, B-37, B-40 and B-47 were tested for wheat leaf rust control. This compound showed a control value of 75% or more.

[Antibacterial test]
(Test example) Antibacterial test against Fusarium graminearum Spores of Fusarium graminearum were added to Minimal SD Base medium containing glucose and dispersed, and then a pyridazinone compound dissolved in dimethyl sulfoxide was added and mixed to a concentration of 25 ppm. The cells were dispensed onto well microplates and incubated in the dark at 25°C for 3 days. After culturing, the turbidity at a wavelength of 405 nm was measured with a microplate reader, and the growth inhibition rate (%) of Fusarium graminearum was determined in comparison with the untreated case.
As a result, the following compounds showed an excellent growth inhibition rate of 50% or more.
Compound number: B-1, B-2, B-3, B-4, B-5, B-6, B-7, B-8, B-9, B-10, B-11, B-12 , B-13, B-14, B-15, B-16, B-17, B-18, B-19, B-20, B-21, B-22, B-24, B-25, B -26, B-27, B-28, B-29, B-30, B-33, B-34, B-36, B-37, B-38, B-39, B-40, B-41 , B-43, B-44, B-45, B-46, B-47, B-50, B-53, C-16, C-17, C-18, C-19.

Claims

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

[In formula (I),
Y represents an oxygen atom or a sulfur atom;
X 1 and X 2 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6- 10 arylsulfonyl group, substituted or unsubstituted 5- to 6-membered heterocyclyl group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, nitro group, cyano group, group represented by R 1 -CO- , a carboxy group, a group represented by R 2 —O—CO—, a group represented by R 3 R 4 N—, a group represented by R 3 R 4 N—CO—, R 1 —CO—O— a group represented by R 1 -CO-NR 5 -, a group R 2 -O-CO-O-, a group R 2 -O-CO-NR 5 - , a group represented by R 3 R 4 N—CO—O—, a group represented by R 3 R 4 N—CO—NR 5 —, a group represented by R 2 SO 2 —NR 5 —, R 3 a group represented by R 4 N--SO 2 --, a group represented by R 1 ON=CR 6 --, a group represented by R 3 R 4 N--N=CR 6 --, or R 1 --N represents a group represented by =CR 6 -;
R 1 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R 2 is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R 3 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
each R 4 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein R 3 and R 4 may together form a divalent organic group,
each R 5 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R 6 is a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted a substituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group;
X 3 is a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R 1 -CO A group represented by -, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4- to 6-membered heterocyclyl group, R N1 O- a group represented by R N1 --CO--O--, a group represented by R N1 --O--CO--O--, a group represented by R N1 R N1 N--CO--O--, and R N1 A group represented by -CS-O-, a group represented by R N1 R N1 N-CS-O-, a group represented by R N1 R N2 N-, a group represented by R N1 -CO-NR N2 - a group represented by R N1 -CO-CO-NR N2 -, a group represented by R N1 -O-CO-NR N2 -, a group represented by R N1 R N1 N-CO-NR N2 - a group represented by R N1 R N1 N—CO—CO—NR N2 —, a group represented by R N1 —CS-NR N2 —, and a group represented by R N1 R N1 N—CS-NR N2 — a group represented by R N1 SO 2 —NR N2 —, or a group represented by R N1 —C(=NR N1 )—NR N2 —,
R N1 and R N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R N1 and R N1 , or R N1 and R N2 may together form a divalent organic group;
X 4 is a group represented by QA-, a group represented by QAB-, a group represented by QBA-, or represented by Q-SO 2 -NR N3 - a group represented by Q—C(R 7 )=N—, a group represented by Q—NR N3 —SO 2 —, a group represented by Q—N=C(R 7 )—, or Q - represents a group represented by B-,
A is each independently a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or a carbonyl group,
B each independently represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR N3 -, where R N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a formyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group,
R 7 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group. ]
The compound or a salt thereof according to claim 1, wherein X 2 is a group represented by R 1 ON=CR 6 -.
An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 or 2 and salts thereof.
The agricultural and horticultural fungicide according to claim 3, which is for seed treatment.
A nematicide containing at least one selected from the group consisting of the compound according to claim 1 or 2 and salts thereof as an active ingredient.
A medical/veterinary antifungal agent containing, as an active ingredient, at least one selected from the group consisting of the compounds according to claim 1 or 2 and salts thereof.
A compound represented by formula (II) or a salt thereof.

[In formula (II),
Y represents an oxygen atom or a sulfur atom;
X 1 and X 2 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6- 10 arylsulfonyl group, substituted or unsubstituted 5- to 6-membered heterocyclyl group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, nitro group, cyano group, group represented by R 1 -CO- , a carboxy group, a group represented by R 2 —O—CO—, a group represented by R 3 R 4 N—, a group represented by R 3 R 4 N—CO—, R 1 —CO—O— a group represented by R 1 -CO-NR 5 -, a group R 2 -O-CO-O-, a group R 2 -O-CO-NR 5 - , a group represented by R 3 R 4 N—CO—O—, a group represented by R 3 R 4 N—CO—NR 5 —, a group represented by R 2 SO 2 —NR 5 —, R 3 a group represented by R 4 N--SO 2 --, a group represented by R 1 ON=CR 6 --, a group represented by R 3 R 4 N--N=CR 6 --, or R 1 --N represents a group represented by =CR 6 -;
R 1 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R 2 is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R 3 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
each R 4 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein R 3 and R 4 may together form a divalent organic group,
each R 5 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R 6 is a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted a substituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group;
X 3 is a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R 1 -CO A group represented by -, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4- to 6-membered heterocyclyl group, R N1 O- a group represented by R N1 --CO--O--, a group represented by R N1 --O--CO--O--, a group represented by R N1 R N1 N--CO--O--, and R N1 A group represented by -CS-O-, a group represented by R N1 R N1 N-CS-O-, a group represented by R N1 R N2 N-, a group represented by R N1 -CO-NR N2 - a group represented by R N1 -CO-CO-NR N2 -, a group represented by R N1 -O-CO-NR N2 -, a group represented by R N1 R N1 N-CO-NR N2 - a group represented by R N1 R N1 N—CO—CO—NR N2 —, a group represented by R N1 —CS-NR N2 —, and a group represented by R N1 R N1 N—CS-NR N2 — a group represented by R N1 SO 2 —NR N2 —, or a group represented by R N1 —C(=NR N1 )—NR N2 —,
R N1 and R N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R N1 and R N1 , or R N1 and R N2 may together form a divalent organic group;
X 5 represents a group represented by HO-A-, a C1-6 alkoxycarbonyl group, or a halogeno group,
A is a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or carbonyl indicates a group. ]
8. The compound or a salt thereof according to claim 7, wherein X 2 is a group represented by R 1 ON=CR 6 -.