WO2023204124A1

WO2023204124A1 - Pyridazinone compound, agricultural and horticultural germicide, nematicide, and medical and veterinary antifungal agent

Info

Publication number: WO2023204124A1
Application number: PCT/JP2023/014914
Authority: WO
Inventors: 真実岸本; 頼人 ▲桑▼原; 達弘川▲崎▼; 伸哉幸堀; 貴昭寺西; 睦幸斎賀
Original assignee: 日本曹達株式会社
Priority date: 2022-04-20
Filing date: 2023-04-12
Publication date: 2023-10-26

Abstract

The present invention addresses the problem of providing: a pyridazinone compound having excellent bactericidal/antibacterial activities and excellent safety and capable of being synthesized industrially advantageously; an agricultural and horticultural germicide containing the pyridazinone compound as an active ingredient; and others.　The pyridazinone compound according to the present invention 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 halogeno group, a substituted or unsubstituted C1-6 alkyl group, or the like; X3 represents a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, or the like; X4 represents a group represented by -A-Q, a group represented by -B-A-Q, or the like; A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 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 5- to 10-membered heterocyclyl group.

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, excellent safety, and can be synthesized industrially advantageously, and an agricultural and horticultural fungicide containing this compound as an active ingredient. Furthermore, the present invention relates to a nematicide containing the above-mentioned compound as an active ingredient. Furthermore, the present invention relates to a medical/veterinary antifungal agent containing the above-mentioned compound as an active ingredient.
This application claims priority to Japanese Patent Application No. 2022-69404 filed on April 20, 2022, the contents of which are incorporated herein.

Various compounds have been proposed that have control activity against crop diseases in the cultivation of agricultural and horticultural crops. In order for such compounds to be put to practical use as agricultural and horticultural fungicides, they must not only have sufficiently high efficacy, but also be unlikely to cause drug resistance, cause no chemical damage to plants or soil contamination, and must be effective against livestock, fish, etc. It is required to have low toxicity to.

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

WO2021/085389A

An object of the present invention is to provide a pyridazinone compound that has excellent bactericidal and antibacterial activity, excellent safety, and can be synthesized industrially advantageously, and an agricultural and horticultural fungicide containing this compound as an active ingredient. A further object of the present invention is to provide a nematicide containing the above-mentioned compound as an active ingredient. A further object of the present invention is to provide an antifungal agent for medical and veterinary use containing the above-mentioned compound as an active ingredient.

As a result of intensive studies to solve the above problems, the present inventors have completed the present invention, which includes 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 C3-6 cycloalkyloxy group Substituted 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 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- , carboxy group, group represented by R ² -O-CO-, group represented by R ³ R ⁴ N-, group represented by R ³ R ⁴ N-CO-, R ¹ -CO-O- A group represented by R ¹ -CO-NR ⁵ -, a group represented by R ² -O-CO-O-, 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 ³ A group represented by R ⁴ N-SO ₂ -, a group represented by R ¹ O-N=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,
^R2 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,
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,
R ⁴ each 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 be combined to form a divalent organic group,
R ⁵ each 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 hydrogen atom, 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, Represents a substituted or unsubstituted 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-, R ^N1 -CS-O-, R ^N1 R ^N1 N-CS-O-, R ^N1 R ^N2 N-, 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 - group, R ^N1 R ^N1 N-CO-CO-NR ^N2 -, R ^N1 -CS-NR ^N2 -, R ^N1 R ^N1 N-CS-NR ^N2 - group, 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 straight chain C1-6 alkyl group, a substituted or unsubstituted straight chain C2-6 alkenyl group, a substituted or unsubstituted straight chain C2-6 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, where R ^N1 and R ^N1 , or R ^N1 and R ^N2 may be taken together to form a divalent organic group;
X ⁴ represents a group represented by -AQ, a group represented by -B-A-Q, a group represented by -A-B-Q, or a group represented by -B-Q; ,
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 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 -, and R ^N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, Represents a formyl group or a substituted or unsubstituted C1-6 alkylcarbonyl group,
Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.

[2] An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] and their salts.
[3] The agricultural and horticultural fungicide according to [2], which is for seed treatment.
[4] A nematicide containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] and salts thereof.
[5] A medical/veterinary antifungal agent containing as an active ingredient at least one compound selected from the group consisting of the compound described in [1] and a salt thereof.

The pyridazinone compound of the present invention has excellent bactericidal and antibacterial activity, reliable effects, excellent safety, and can be industrially advantageously synthesized.
The agricultural and horticultural fungicides and nematicides of the present invention have excellent pesticidal effects, do not cause chemical damage to plants, have little toxicity to animals, fish, and have little impact on the environment.
The medical and veterinary antifungal agent of the present invention has an excellent antibacterial effect and has low toxicity to mermaids and fishes.

[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 the core group. When only the name of the core group is stated, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of the group serving as the mother nucleus is substituted with a group having the same or a different structure from the mother nucleus. Therefore, a "substituent" is another group bonded to the core group. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.

The "substituent" is not particularly limited as long as it is chemically permissible and has the effects of the present invention.
Specific examples of groups that can be "substituents" include the following groups.
Halogeno groups such as fluoro group, chloro group, bromo group, iodo group;
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, etc. 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;

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

Hydroxyl group;
C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group;
C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group;
C6-10 aryloxy groups such as phenoxy groups and naphthoxy groups;
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 acetyloxy groups and propionyloxy groups;
C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, 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 group such as 3,3-difluorocyclobutyl group;
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, trichloroacetyl group;

Amino group;
C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, 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 groups 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) - Substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as imino)ethyl group;
Aminocarbonyloxy group;
C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy groups and dimethylaminocarbonyloxy groups;

Mercapto group;
C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group;
C2-6 alkenylthio groups such as vinylthio group and allylthio group;
C2-6 alkynylthio groups such as ethynylthio group and propargylthio group;
C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group;
C2-6 alkenylsulfinyl groups such as allylsulfinyl groups;
C2-6 alkynylsulfinyl group such as propargylsulfinyl group;
C1-6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group;
C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 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 alkylsulfoximino group such as S,S-dimethylsulfoximino group;

TriC1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
triC6-10 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 a core is 1 to 6. This number of carbon atoms does not include the number of carbon atoms present in substituents. For example, an ethoxybutyl group is classified as a C2 alkoxyC4 alkyl group because the core group is a butyl group and the substituent is an ethoxy group.

Furthermore, the above-mentioned "3- to 6-membered heterocyclyl group" includes 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms as ring constituent atoms. Examples of the "3- to 6-membered heterocyclyl group" include saturated 3- to 6-membered heterocyclyl groups, 5- to 6-membered heteroaryl groups, and partially unsaturated 5- to 6-membered heterocyclyl groups. .

Examples of 3- to 6-membered saturated heterocyclyl groups include aziridinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, Examples include dioxolanyl group and dioxanyl group.

Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group. can be mentioned.
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
Examples of the 5-membered partially unsaturated heterocyclyl group include a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and an isoxazolinyl group.
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 C3-6 cycloalkyloxy group Substituted 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 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- , carboxy group, group represented by R ² -O-CO-, group represented by R ³ R ⁴ N-, group represented by R ³ R ⁴ N-CO-, R ¹ -CO-O- A group represented by R ¹ -CO-NR ⁵ -, a group represented by R ² -O-CO-O-, 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 ³ A group represented by R ⁴ N-SO ₂ -, a group represented by R ¹ O-N=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.
^R2 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.
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.
R ⁴ each 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 be combined to form a divalent organic group.
R ⁵ each 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 hydrogen atom, 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, It represents a substituted or unsubstituted 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, an iodo group, and the like.

The "C1-6 alkyl group" in X ¹ and X ² may be linear or branched. Examples of the "C1-6 alkyl group" in X ¹ include 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" in X ¹ and X ² include 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, Examples include 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group.

Examples of the "C2-6 alkynyl group" in X ¹ and X ² include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 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, Examples include 1-hexynyl group and 1,1-dimethyl-2-butynyl group.

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

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

"C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkyl group" in X 1 ^and X ² Examples of substituents on the "C1-6 alkynyloxy group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group" include fluoro group, chloro group, bromo group, and iodo group. Halogeno groups such as; hydroxyl groups; C1-6 alkoxy groups such as methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, n-butoxy groups, s-butoxy groups, i-butoxy groups, t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; (C1-6 haloalkoxy groups such as (ethylideneamino)oxy group, propan-2-ylideneamino)oxy group 6-alkylidene amino)oxy group; C3-6 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; C6-10 aryl group such as phenyl group, naphthyl group; 4-methylphenyl group, 4-methoxy group C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 alkyl group, 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 group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group a 5-membered heteroaryl group such as a group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group; 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 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 of 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" in 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 a phenyl group, a naphthyl group, an indanyl group, an indenyl group, a tetralinyl group, and the like.
Examples of the "C6-10 aryloxy group" for X ¹ and X ² include phenoxy group and naphthoxy group.

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

The "5- to 6-membered heterocyclyl group" in X ¹ ^and It 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 5- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups. .

Examples of the 5- to 6-membered saturated heterocyclyl group include 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, a dioxanyl group, and the like.
Examples of the 5- to 6-membered heteroaryl group include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, and tetrazolyl group. 5-membered heteroaryl groups such as; and 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl groups.
Examples of 5- to 6-membered ring partially unsaturated heterocyclyl groups include 5-membered ring partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, and isoxazolinyl group; Mention may be made of six-membered partially unsaturated heterocyclyl groups such as pyranyl groups.

The "5- to 6-membered heterocyclyloxy group" in 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 thiazolyloxy group and 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 a "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "5- to 6-membered heterocyclyl group", or "5- to 6-membered heterocyclyloxy group", fluoro group , halogeno groups such as chloro group, bromo group, iodo 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, 1-fluoro-n-butyl group, etc. 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 ; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group, C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, such as 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, or C6-10 aryl group substituted with any one or more substituents of C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group a 5-membered heteroaryl group such as a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group; 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 substituted with any one or more substituents; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; C1-6 alkyl group, A 6-membered heteroaryl group substituted with one or more substituents of a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a cyano group is preferred.
Furthermore, as a substituent on a "C3-6 cycloalkyl group,""C3-6 cycloalkyloxy group,""5- to 6-membered heterocyclyl group," or "5- to 6-membered heterocyclyloxy group," , oxo group is also preferred.

In the "group represented by R ¹ -CO-" in 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 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.

Examples of the "C1-6 alkyl group" in R ¹ include 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 ethynyl group and 1-propynyl group.
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 group, chloro group, bromo group, and iodo 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 - C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; phenyl group, naphthyl group 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 of C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl 5-membered heteroaryl groups such as groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, and tetrazolyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno 5-membered heteroaryl group substituted with one or more substituents of C1-6 haloalkyl group, C1-6 haloalkoxy group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. 6-membered heteroaryl group; 6 substituted with 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 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, and a cyclohexyl group.
Examples of the "C6-10 aryl group" for R ¹ include phenyl group, naphthyl group, indenyl group, indanyl group, and tetralinyl group.

The "5- to 6-membered heterocyclyl group" in R ¹ is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms as ring constituent 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 5- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups. .
Examples of the 5- to 6-membered saturated heterocyclyl group include 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, a dioxanyl group, and the like.
Examples of the 5- to 6-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group. 5-membered heteroaryl groups such as; and 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl groups.
Examples of 5- to 6-membered ring partially unsaturated heterocyclyl groups include 5-membered ring partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, and isoxazolinyl group; Examples include 6-membered partially unsaturated heterocyclyl groups such as pyranyl groups.

Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- to 6-membered heterocyclyl group" in R ¹ include fluoro group, chloro group, bromo group, iodo group, etc. 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; C1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; methoxy group , C1-6 alkoxy groups such as 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, 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, 4-chlorophenyl group , 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or 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 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 5-membered heteroaryl group; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 -6-membered heteroaryl group substituted with one or more substituents of C1-6 haloalkyl group or C1-6 haloalkoxy group; or cyano group is preferred.
Furthermore, as a substituent on the "C3-6 cycloalkyl group" or the "5- to 6-membered heterocyclyl group", an oxo group is also preferred.

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

In the "group represented by R ² -O-CO-" in 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 the substituent for R ² include the same ones as exemplified for R ¹ .

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

In the "group represented by R ³ R ⁴ N-" in 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, Indicates 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 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 the substituent for R ³ or R ⁴ include the same ones as exemplified for R ¹ .

Here, R ³ and R ⁴ may be combined to form a divalent organic group.
Examples of the divalent organic group that can be formed include a substituted or unsubstituted C2-5 alkylene group or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group.
Examples of the "C2-5 alkylene group" include dimethylene group, trimethylene group, and tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include dimethyleneoxydimethylene group and the like.
Substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxyC1-3 alkylene group" include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; methyl group, ethyl group, n - C1-6 alkyl group 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, and 1-fluoro-n-butyl group are preferred.

Specific examples of "the group represented by R ³ R ⁴ N-" include an amino group, a methylamino group, a dimethylamino group, an i-propylamino group, and the like.

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

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

In the "group represented by R ¹ --CO-NR ⁵ --" in X ¹ and X ² , R ¹ has the same meaning as in 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 the substituent for R ⁵ include the same ones as 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 ² -O-CO-O-" in X ¹ and X ² , R ² has the same meaning as in the above "group represented by R ² -O-CO-" .
Specific examples of "the group represented by R ² --O--CO--O-" include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, and the like.

In the "group represented by R ² -O-CO-NR ⁵ -" in 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 —”.
A specific example of “the group represented by R ² —O—CO—NR ⁵ —” includes a methoxycarbonylamino group.

In the "group represented by R ³ R ⁴ N-CO-O-" in 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 "a group represented by R ³ R ⁴ N-CO-O-" include a carbamoyloxy group, an N,N-dimethylaminocarbonyloxy group, and the like.

In the "group represented by R ³ R ⁴ N-CO-NR ⁵ -" in 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 a similar meaning. 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 --" in X ¹ and X ² , R ² has the same meaning as in 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 —”.
A specific example of "the group represented by R ² SO ₂ --NR ⁵ --" includes a methanesulfonylamino group.

In the "group represented by R ³ R ⁴ N-SO ₂ --" in 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-" Show meaning.
A specific example of "the group represented by R ³ R ⁴ N-SO ₂ --" includes an N,N-dimethylaminosulfonyl group.

In the "group represented by R ¹ O--N=CR ⁶ --" in X ¹ and X ² , R ¹ has the same meaning as in the above-mentioned "group represented by R ¹ --CO--".
R ⁶ is a hydrogen atom, 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, It represents a substituted or unsubstituted 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" in R ^{6 can be the same as those exemplified in R 1} ^. .
Examples of the "halogeno group" for R ⁶ include a fluoro group, a chloro group, a bromo group, an iodo group, and the like.
Examples of the "mono C1-6 alkylamino group" of the "substituted or unsubstituted mono C1-6 alkylamino group" in R ⁶ include a methylamino group, an ethylamino group, an i-propylamino group, and the like.
Examples of the "di-C1-6 alkylamino group" of "substituted or unsubstituted di-C1-6 alkylamino group" in R ⁶ include dimethylamino group, diethylamino group, N-methyl-N-i-propylamino group, etc. can be mentioned.
Examples of the "C1-6 alkoxy group" of the "substituted or unsubstituted C1-6 alkoxy group" in R ⁶ include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n- Examples include hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, and i-hexyloxy group.
The "C1-6 alkylthio group" of "substituted or unsubstituted C1-6 alkylthio group" in R ⁶ includes methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group. and i-propylthio group.
The substituents on the "C1-6 alkoxy group", "mono-C1-6 alkylamino group", "di-C1-6 alkylamino group", or "C1-6 alkylthio group" in ^{R 6} ^include " Examples of the substituents on the C1-6 alkyl group include the same substituents as those exemplified above.
Specific examples of "the group represented by R ¹ O-N=CR ⁶ -" include (hydroxyimino)methyl group, (ethoxyimino)methyl group, 1-(i-propoxyimino)ethyl group, etc. Can be done.

In the "group represented by R ³ R ⁴ NN=CR ⁶ --" in 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 a similar meaning. R ⁶ has the same meaning as in the above “group represented by R ¹ O—N=CR ⁶ —”.

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

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

[X ³ ]
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 It represents 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 "straight chain 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.
Examples of the "linear C2-6 alkenyl group" in X ³ include vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2- Examples include pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, and 5-hexenyl group.
Examples of the "linear C2-6 alkynyl group" in X ³ include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2- Examples include pentynyl group, 3-pentynyl group, 4-pentynyl group, and 1-hexynyl group.
Examples of the "4-membered heterocyclyl group" for X ³ include azetidinyl group and oxetanyl group.
Specific examples of other substituents for X ³ include the same ones as exemplified for X ¹ and X ² .

In the present invention, preferred examples of X ³ include 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.

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 As the substituent on the aryl group or the substituent on the 4- to 6-membered heterocyclyl group, one or more substituents selected from the following substituent groups can be mentioned (hereinafter, this substituent may be represented by the symbol "G").
Furthermore, when there are two or more substituents (G), two of them may be combined to form a divalent organic group. The 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- group represented by R ^c R ^d N-, group represented by R ^c R ^d N-CO-, group represented by R ^c R ^d N-NR ^d -CO-, R ^b SO ₂ -NR ^d -CO-, R ^a -CO-O-, R ^a -CO-NR ^e -, 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-, a group represented by 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 -, a group represented by 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 O-N=CR ^f -, R ^h R ^j a group represented by C=N-O-, a group represented by R ^a -C(=NR ^g )-NR ^e -, R ^c R ^d N-C(=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 group, R ^a 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, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 10-membered heterocyclyl group.
R ^b 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 ^c 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 ^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, where: R ^c and R ^d may be taken together to form a divalent organic group.
R ^e 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 ^f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
R ^g each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
R ^h each independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group.
R ⁱ each independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group, where R ^h and R ⁱ together represent a divalent An organic group may also be formed.

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

The "C1-6 alkyl group" in G may be linear or branched.
Examples of the "C1-6 alkyl group" in G include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s- Examples include butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group.

Examples of the "C2-6 alkenyl group" in G include 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, etc.

Examples of the "C2-6 alkynyl group" in G include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group , 1,1-dimethyl-2-butynyl group, and the like.

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

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

"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”, substituents include halogeno groups such as fluoro group, chloro group, bromo group, iodo group, etc. ; Hydroxyl group; C1-6 alkoxy groups 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- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C1-6 alkylthio groups such as methylthio group, ethylthio group; C1-6 alkylthio groups such as methylsulfinyl group, ethylsulfinyl group, etc. 6-alkylsulfinyl group; C1-6 alkylsulfonyl group such as methylsulfonyl group, ethylsulfonyl group; C3-6 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; C6 such as phenyl group, 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 a C6-10 aryl group substituted with one or more substituents of a group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group , oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. 5-membered heteroaryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 A 5-membered heteroaryl group substituted with one or more substituents of a 6-haloalkyl group or a C1-6 haloalkoxy group; a 6-membered ring such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. heteroaryl group; a 6-membered heteroaryl group substituted with 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; An aryl group; or a cyano group is preferred.

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

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

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

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

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

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 thiazolyloxy group and pyridyloxy group.

"C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 aryloxy group" in G Substituents on the "arylsulfinyl group", "C6-10 arylsulfonyl group", "3- to 10-membered heterocyclyl group", or "3- to 10-membered heterocyclyloxy group" include fluoro group, 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 group such as n-hexyl group; C1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group 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 C1-6 haloalkoxy group such as -n-propoxy group, 2,3-dichlorobutoxy group, 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 (C6-10 aryl) substituted with one or more substituents of C1-6 haloalkoxy group; 5-membered heteroaryl C1-6 alkoxy group; (with 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) 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 heteroaryl substituted with one or more substituents of C1-6 haloalkoxy group) C1-6 alkoxy group; C1-6 alkylthio group such as methylthio group, ethylthio group; methylsulfinyl group, ethyl C1-6 alkylsulfinyl groups such as sulfinyl groups; C1-6 alkylsulfonyl groups such as methylsulfonyl and ethylsulfonyl groups; C1-6 haloalkylthio such as trifluoromethylthio and 2,2,2-trifluoroethylthio groups Group: C1-6 haloalkylsulfinyl group such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group; C1-6 such as trifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group Haloalkylsulfonyl group; C3-6 cycloalkyl group such as cyclopropyl group, cyclobutyl group; 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 any one or more substituents; C3-6 cycloalkenyl group; C6-10 aryl group such as phenyl group, naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group , 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 halo C6-10 aryl group substituted with any one or more substituents of alkoxy group; 3- to 4-membered saturated heterocyclyl group such as aziridinyl group, epoxy group, azetidinyl group, oxetanyl group; C1-6 alkyl group, C1 ~3- to 4-membered saturated heterocyclyl group substituted with one or more substituents of ~6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; pyrrolidinyl group, tetrahydrofuranyl group, 5- to 6-membered saturated heterocyclyl groups such as thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , C1-6 haloalkyl group, or C1-6 haloalkoxy group, a 5- to 6-membered saturated heterocyclyl 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. 5-membered heteroaryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 5-membered heteroaryl group substituted with one or more substituents of 6-haloalkyl group or C1-6-haloalkoxy group; 6-membered ring such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. heteroaryl group; a 6-membered heteroaryl group substituted with 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 Aryl group; 5-membered partially unsaturated heterocyclyl group such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group; C1-6 alkyl group, C1-6 alkoxy group, A partially saturated 5-membered heterocyclyl group substituted with one or more substituents of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a partially unsaturated 6-membered ring such as a dihydropyranyl group Heterocyclyl group; 6-membered partially saturated heterocyclyl group substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group Base;
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, A 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 C1-10 aryl substituted with one or more substituents of haloalkyl group or C1-6 haloalkoxy group) C1-6 alkyl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 ~5- to 6-membered heteroaryl substituted with one or more substituents of ~6 haloalkyl group or 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 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 A C6-10 aryl group substituted with any one or more substituents of a C1-6 haloalkoxy group; a 5- to 6-membered heteroaryl group; or; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group , a 5- to 6-membered heteroaryl group substituted with one or more substituents of a C1-6 haloalkyl group, or a C1-6 haloalkoxy group. 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; halogeno group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, 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 group) (C1-6 alkyl group, C1-6 alkyl group, C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 aryl substituted with one or more substituents of C1-6 haloalkoxy group) 5- to 6-membered heteroaryl substituted with one or more substituents of 6-haloalkyl group or 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 A C3-6 cycloalkyl group substituted with 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 a C1-6 haloalkoxy group C6-10 aryl group substituted with one or more substituents; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1 - 6 A 5- to 6-membered heteroaryl group substituted with one or more substituents of haloalkoxy groups; The same applies to R ^G2 below);
R ^G1 R ^G1 A group represented by N- (R ^G1 in the formula may be the same or different. R ^G1 together form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxy may form a dimethylene group);
R ^G1 R ^G1 A group represented by N-CO- (R ^G1 in the formula may be the same or different. R ^G1 together form a trimethylene group, tetramethylene group, pentamethylene group, or diamethylene group) may form a methyleneoxydimethylene group);
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 a C1-6 alkyl group substituted with one or more substituents of a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- to 6-membered heteroaryl group; a C6-10 aryl) C1-6 alkyl group substituted with 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; or (5- to 6-membered heteroaryl substituted with 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) Indicates a C1-6 alkyl group; the same applies to R ^G3 below);
R ^G2 -O-CO-O- group; R ^G2 -O-CO-NR ^G3 - group; R ^G1 R ^G1 N-CO-O- group (in the formula R ^G1 may be the same or different. R ^G1 may be taken together to 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 - (R ^G1 in the formula may be the same or different. R ^G1 together form 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. R ^G1 may be taken together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
A group represented by R ^G1 -O-N=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 ^G1 in the formula may be the same or different. R ^G1 together form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group) );
A pentafluorosulfanyl group, a nitro group, or a cyano group is preferred.
Furthermore, as a substituent on a "C3-6 cycloalkyl group,""C3-6 cycloalkyloxy group,""3- to 10-membered heterocyclyl group," or "3- to 10-membered heterocyclyloxy group," , oxo group is also preferred.

In the "group represented by R ^a -CO-" in 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 C2-6 alkenyl group, or a substituted or unsubstituted C2-6 alkenyl group. 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.

Examples of the "C1-6 alkyl group" in R ^a include 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 ethynyl group and 1-propynyl group.
Substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in ^R a include halogen groups such as fluoro group, chloro group, bromo group, and iodo 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 - C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C1-6 alkylthio groups such as methylthio group and ethylthio group: C1-6 such as methylsulfinyl group and ethylsulfinyl group Alkylsulfinyl group; C1-6 alkylsulfonyl group such as methylsulfonyl group and ethylsulfonyl group; Carboxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t - C1-6 alkoxycarbonyl groups such as butoxycarbonyl groups; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; C6-10 aryl groups such as phenyl and naphthyl groups; 4-methyl C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 alkyl group, such as phenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group C6-10 aryl group substituted with one or more substituents of haloalkyl group or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group 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, C1-6 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 of an alkyl group, a C1-6 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 ^R a include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
Examples of the "C6-10 aryl group" for ^R a include phenyl group, naphthyl group, indenyl group, indanyl group, and tetralinyl group.

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

Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "3- to 10-membered heterocyclyl group" in ^R a include fluoro group, chloro group, bromo group, iodo group, etc. 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; C1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; methoxy group , C1-6 alkoxy groups such as 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, C1-6 haloalkoxy group such as 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10 aryl C1-6 alkoxy group; (C1-6 alkyl group, C1 ~C6-10 aryl substituted with one or more substituents of ~6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkoxy group; 5-membered heteroaryl C1-6 alkoxy group; (5-membered ring substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) 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 heteroaryl substituted with one or more substituents) C1-6 alkoxy group; C1-6 alkylthio group such as methylthio group, ethylthio group: C1-6 alkylthio group such as methylsulfinyl group, ethylsulfinyl group, etc. 6-alkylsulfinyl group; C1-6 alkylsulfonyl group such as methylsulfonyl group and ethylsulfonyl group; C1-6 haloalkylthio group such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group: trifluoromethylsulfinyl group, C1-6 haloalkylsulfinyl group such as 2,2,2-trifluoroethylsulfinyl group; C1-6 haloalkylsulfonyl group such as trifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group; cyclopropyl a C3-6 cycloalkyl group such as a cyclobutyl group, a cyclopentyl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group C3-6 cycloalkyl group substituted with one or more substituents; C3-6 cycloalkenyl group; C6-10 aryl group such as phenyl group, naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4- C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group such as chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group C6-10 aryl group substituted with one or more substituents; 3- to 4-membered saturated heterocyclyl group such as aziridinyl group, epoxy group, azetidinyl group, oxetanyl group; C1-6 alkyl group, C1-6 alkoxy a 3- to 4-membered saturated heterocyclyl group substituted with one or more substituents of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, 5- to 6-membered saturated heterocyclyl group such as tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 A 5- to 6-membered saturated heterocyclyl group substituted with one or more substituents of a 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 group, tetrazolyl group, etc. 5-membered heteroaryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group , or a 5-membered heteroaryl group substituted with one or more substituents of a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. group; a 6-membered heteroaryl group substituted with 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; 5-membered ring partially unsaturated heterocyclyl group such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, A 5-membered ring partially saturated heterocyclyl group substituted with one or more substituents of a C1-6 haloalkyl group or a C1-6 haloalkoxy group; a 6-membered ring partially unsaturated heterocyclyl group such as a dihydropyranyl group; a 6-membered partially saturated heterocyclyl group substituted with 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;
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, A 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 C1-10 aryl substituted with one or more substituents of haloalkyl group or C1-6 haloalkoxy group) C1-6 alkyl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 ~5- to 6-membered heteroaryl substituted with one or more substituents of ~6 haloalkyl group or 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 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 A C6-10 aryl group substituted with any one or more substituents of a C1-6 haloalkoxy group; a 5- to 6-membered heteroaryl group; or; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group , a 5- to 6-membered heteroaryl group substituted with one or more substituents of 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, 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 group) (C1-6 alkyl group, C1-6 alkyl group, C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 aryl substituted with one or more substituents of C1-6 haloalkoxy group) 5- to 6-membered heteroaryl substituted with one or more substituents of 6-haloalkyl group or 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 A C6-10 aryl group substituted with any one or more substituents of ~6 haloalkoxy groups; a 5- to 6-membered heteroaryl group; or a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, Indicates a 5- to 6-membered heteroaryl group substituted with one or more substituents of a C1-6 haloalkyl group or a C1-6 haloalkoxy group. The same applies to R ^q2 below);
R ^q1 R ^q1 Group represented by N- (R ^q1 in the formula may be the same or different. R ^q1 together represent a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group);
R ^q1 R ^q1 A group represented by N-CO- (R ^q1 in the formula may be the same or different. R ^q1 together represent a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyl may form a methyleneoxydimethylene group);
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 a C1-6 alkyl group substituted with one or more substituents of a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- to 6-membered heteroaryl group; a C6-10 aryl) C1-6 alkyl group substituted with 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; or (5- to 6-membered heteroaryl substituted with 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) represents a C1-6 alkyl group; the same applies to R ^q3 below);
R ^q2 Group represented by -O-CO-O-; R ^q2 -O-CO-NR ^q3 Group represented by -; R ^q1 R ^q1 Group represented by N-CO-O- (in the formula R ^q1 may be the same or different. R ^q1 may be taken together 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 - (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 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. R ^q1 may be taken together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
R ^q1 -O-N=C(R ^q4 )- (wherein, R ^q4 represents a hydrogen atom or a C1-6 alkyl group); (R ^q1 ) ₂ C=N-O- A group represented by (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) );
A pentafluorosulfanyl group, a nitro group, or a cyano group is preferred.
Furthermore, as a substituent on the "C3-6 cycloalkyl group" or the "3- to 10-membered heterocyclyl group", an oxo group is also preferred.

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-" in 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 "a 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. Examples include groups.

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

Here, R ^c and R ^d may be combined to form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups, substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups, substituted or unsubstituted C1-3 alkylenethio C1-3 Examples include an alkylene group, a substituted or unsubstituted C1-3 alkyleneimino C1-3 alkylene group, and the like.
Furthermore, silicon-containing divalent hydrocarbon groups such as -CH ₂ CH ₂ -Si(CH ₃ ) ₂ -CH ₂ CH ₂ - can be mentioned.
Examples of the "C2-5 alkylene group" include dimethylene group, trimethylene group, and tetramethylene group.
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 dimethylenethiodi dimethylene group and the like.
Examples of the "C1-3 alkyleneimino C1-3 alkylene group" include dimethyleneimino dimethylene group and the like.
Here, the imino group of "C1-3 alkylene alkyleneimino 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 fluoro group, chloro group, bromo group, iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl 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, etc. ~6 haloalkyl groups are preferred.

Specific examples of "the group represented by R ^c R ^d N-" include an amino group, a methylamino group, a dimethylamino group, an i-propylamino group, and the like.

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

In the "group represented by R ^c R ^d N-NR ^d -CO-" in G, R ^c and R ^d have the same meanings as those in the above "group represented by R ^c R ^d N-". show.
A specific example of the "group represented by R ^c R ^d N-NR ^d -CO-" includes a 2,2-dimethylhydrazine-1-carbonyl group.

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

In the "group represented by R ^a -CO-O-" in G, R ^a has the same meaning as in the above-mentioned "group represented by R ^a -CO-".
A specific example of the "group represented by R ^a -CO-O-" includes an acetyloxy group.

In the "group represented by R ^a --CO-NR ^e --" in 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 include the same ones as 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 -" in G, R ^a has the same meaning as in the above-mentioned "group represented by R ^a -CO-". R ^e has the same meaning as in the above "group represented by R ^a -CO-NR ^e -".
A specific example of "the group represented by R ^a -CO-CO-NR e ^- " includes an oxopropanamide group.

In the "group represented by R ^a --CO-NR ^e --NR ^e --" in G, R ^a has the same meaning as in the above-mentioned "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, an i-propylcarbonylhydrazinyl group, and the like.

In the "group represented by R ^a -CO-NR ^e -NR ^e -CO-" in G, R ^a has the same meaning as in the above-mentioned "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 a 2-acetylhydrazine-1-carbonyl group.

In the "group represented by R ^b --O--CO--O-" in G, R ^b has the same meaning as in the above-mentioned "group represented by R ^b --O--CO-".
Specific examples of "the group represented by R ^b --O--CO--O-" include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, and the like.

In "the group represented by R ^b --O--CO--NR ^e --" in G, R ^b has the same meaning as in the above-mentioned "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 -".
A specific example of "the group represented by R ^b --O-CO-NR ^e --" includes a methoxycarbonylamino group.

In the "group represented by R ^c R ^d N-CO-O-" in 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 -" in G, R ^c and R ^d have the same meanings as 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 -" in G, R ^c and R ^d are the same as those in the above "group represented by R ^c R ^d N-" Show 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-oxoacetamido group, 2-(t-butylamino)-2- Examples include oxoacetamide groups.

In the "group represented by R ^a -CS-NR ^e -" in G, R ^a has the same meaning as in the above-mentioned "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 -" in 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 -".
A specific example of the "group represented by R ^c R ^d N-CS-NR ^e -" includes a 3,3-dimethylthioureido group.

In the "group represented by R ^b SO ₂ --NR ^e --" in 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 -".
A specific example of "the group represented by R ^b SO ₂ --NR ^e --" includes a methanesulfonylamino group.

In the "group represented by R ^c R ^d N--SO ₂ --" in G, R ^c and R ^d have the same meanings as in the above-mentioned "group represented by R ^c R ^d N-".
A specific example of the "group represented by R ^c R ^d N-SO ₂ -" includes an N,N-dimethylaminosulfonyl group.

In the "group represented by R ^a O-N=CR ^f -" in 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 R ^a .
Specific examples of "the group represented by R ^a O-N=CR ^f -" include (hydroxyimino)methyl group, (ethoxyimino)methyl group, and the like.

In the "group represented by R ^a --C(=NR ^g )-NR ^e --" in 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 -".
R ^g each 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 R ^g include the same ones as exemplified for R ^a .

In the "group represented by R ^c R ^d N-C(=NR ^g )-" in G, R ^c and R ^d are the same as those in the above "group represented by R ^c R ^d N-" Show 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-" in G, R ^h is each independently a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C1-6 alkyl group. It 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 the substituent for R ^h or R ⁱ include the same ones as exemplified for R ^a .

Here, R ^h and R ⁱ may be combined to form a divalent organic group.
Examples of the divalent organic group that can be formed include a substituted or unsubstituted C2-5 alkylene group or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group.
Examples of the "C2-5 alkylene group" include dimethylene group, trimethylene group, and tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxyC1-3 alkylene group" include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; methyl group, ethyl group, n - C1-6 alkyl group 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, and 1-fluoro-n-butyl group are preferred.

In the "group represented by R ^h R ⁱ S=N-CO-" in G, R ^h or R ⁱ is the above-mentioned "group represented by R ^h R ⁱ S(=O)=N-CO-" Indicates the same meaning as those in .

In the "R ^h R ^j group represented by C=N-O-" in G, R ^h and R ^j are the same as those in the above "group represented by R ^h R ^j S=N-O-" Indicates the meaning of
A specific example of "a group represented by R ^h R ^j C=N--O-" includes a (propan-2-ylideneamino)oxy group and the like.

When there are two or more substituents (G), examples of the divalent organic group that can be formed by combining two of them include a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxyC1-4 Examples include an alkylene group, a substituted or unsubstituted oxyC2-3 alkyleneoxy group, and a substituted or unsubstituted C1-3 alkyleneoxyC1-3 alkylene group.
Examples of the "C1-5 alkylene group" include methylene group, dimethylene group, trimethylene group, and tetramethylene group.
Examples of the "oxy C1-4 alkylene group" include oxymethylene group and oxydimethylene group.
Examples of the "oxyC2-3 alkyleneoxy group" include an oxydimethyleneoxy group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include dimethyleneoxydimethylene group and the like.
Substituents on "C1-5 alkylene group", "oxyC1-4 alkylene group", "oxyC2-3 alkyleneoxy group", "C1-3 alkyleneoxy C1-3 alkylene group" include fluoro group, chloro C1 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, etc. -6 alkyl group; or C1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, etc. are preferred.

In the present invention, preferred examples of G include 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, and a substituted or unsubstituted C1-6 alkylthio group. 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 Member ring heterocyclyl group, group represented by R ^b -O-CO-, group represented by R ^c R ^d N-, group represented by R ^c R ^d N-CO-, 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 O-N=CR ^f -, or a group represented by R ^h R ⁱ C=N-O-.

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

R ^N1 and R ^N2 are each independently a hydrogen atom, a substituted or unsubstituted straight chain C1-6 alkyl group, a substituted or unsubstituted straight chain C2-6 alkenyl group, a substituted or unsubstituted straight chain C2-6 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, where R ^N1 and R ^N1 or R ^N1 and R ^N2 may be taken together to form a divalent organic group.

Examples of the "linear C1-6 alkyl group" for R ^N1 and R ^N2 include a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, and n-hexyl group.
Examples of the "linear C2-6 alkenyl group" in R ^N1 and R ^N2 include 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.
Examples of the "linear C2-6 alkynyl group" in R ^N1 and R ^N2 include 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 "four-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 include those exemplified for X ¹ .

[X ⁴ ]
X ⁴ represents a group represented by -A-Q, a group represented by -B-A-Q, a group represented by -A-B-Q, or a group represented by -B-Q .

[B]
B represents 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 Indicates 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 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, etc.
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.

Examples of substituents on the "C1-6 alkyl group" and "C1-6 alkyl carbonyl" in R ^N3 include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; hydroxyl group; methoxy group, 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 propan-2-ylideneamino)oxy group; cyclopropyl group, cyclobutyl group , cyclopentyl group, C3-6 cycloalkyl group such as cyclohexyl group; C6-10 aryl group such as phenyl group, naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethyl group With 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 phenyl group or a 4-trifluoromethoxyphenyl group. Substituted C6-10 aryl group; 5-membered 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; 5-membered ring substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group Heteroaryl group; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or A 6-membered heteroaryl group substituted with any one or more substituents of a C1-6 haloalkoxy group; or a cyano group is preferred.

[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 the group.

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

In the present invention, preferred A is a substituted or unsubstituted C1-6 alkylene group or a substituted or unsubstituted C2-6 alkenylene group.
As the substituent on the C1-6 alkylene group or the C2-6 alkenylene group, one or more substituents selected from the following substituent groups can be mentioned (hereinafter, this substituent will be referred to as the symbol "Ga"). ).
Furthermore, when there are two or more substituents (Ga), two of them may be combined to form a divalent organic group. The 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 C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, Substituted 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 ~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-, a group represented by 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 O-N=CR ^f1 -, R ^g1 R ^h1 C=N-O-, oxo group (O=), thioxo group (S=), R ^a1 - Divalent group represented by N=, R ^a1 Divalent group represented by O-N=, R ^c1 R ^d1 Divalent group represented by N-N=, R ^a1 -CO-NR ^e1 -N= divalent group, R ^b1 -O-CO-NR ^e1 -N= divalent group, R ^b1 SO ₂ -NR ^e1 -N= divalent group Base.

In the above substituent group, R ^a1 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, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 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 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 ^c1 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 ^d1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R ^c1 and R ^d1 together represent A divalent organic group may also 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, a 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, and R ^g1 and R ^h1 may be taken together to form a divalent organic group.

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

The "C1-6 alkyl group" in Ga may be linear or branched. Examples of the "C1-6 alkyl group" in Ga include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s- Examples include butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, and i-hexyl group.

Examples of the "C2-6 alkenyl group" in Ga include 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, etc.

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

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

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

"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 Ga ”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, or “C1-6 alkylsulfonyl group”, substituents include halogeno groups such as fluoro group, chloro group, bromo group, iodo group, etc. ; Hydroxyl group; C1-6 alkoxy groups 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- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, 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 , C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; or a cyano group is preferred.

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

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

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

The "3- to 6-membered heterocyclyl group" in Ga is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms as ring constituent 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 saturated 3- to 6-membered heterocyclyl groups, 5- to 6-membered heteroaryl groups, and partially unsaturated 5- to 6-membered heterocyclyl groups. .

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

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 thiazolyloxy group and pyridyloxy group.

"C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 Substituents on the "arylsulfinyl group", "C6-10 arylsulfonyl group", "3- to 6-membered heterocyclyl group", or "3- to 6-membered heterocyclyloxy group" include fluoro group, 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 group such as n-hexyl group; C1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group 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 -C1-6 haloalkoxy groups such as -n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C6-10 aryl groups such as phenyl group, naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or 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-" in 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 C2-6 alkenyl group, or a substituted or unsubstituted C2-6 alkenyl group. 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.

Examples of the "C1-6 alkyl group" in R ^a1 include 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 ethynyl group and 1-propynyl group.
Substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in R ^a1 include halogeno groups such as fluoro group, chloro group, bromo group, and iodo 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 - C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; phenyl group, naphthyl group C6-10 aryl group such as a 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, any of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy 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 cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.
Examples of the "C6-10 aryl group" for R ^a1 include phenyl group and naphthyl group.

The "5- to 6-membered heterocyclyl group" in R ^a1 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as ring constituent 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 5- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups. .
Examples of the 5- to 6-membered saturated heterocyclyl group include 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, a dioxanyl group, and the like.
Examples of the 5- to 6-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group. 5-membered heteroaryl groups such as; and 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl groups.
Examples of 5- to 6-membered ring partially unsaturated heterocyclyl groups include 5-membered ring partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, and isoxazolinyl group; Mention may be made of six-membered partially unsaturated heterocyclyl groups such as pyranyl groups.

Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- to 6-membered heterocyclyl group" in R ^a1 include fluoro group, chloro group, bromo group, iodo group, etc. 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; C1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; methoxy group , C1-6 alkoxy groups such as 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, 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, 4-chlorophenyl group , 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl 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; or a cyano group is preferred.

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

In the "group represented by R ^b1 -O-CO-" in 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 include the same ones as exemplified for R ^a1 .

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

In the "group represented by R ^c1 R ^d1 N-" in Ga, R ^c1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted C2-6 alkenyl group. 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, 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 include the same ones as exemplified for R ^a1 .
Here, R ^c1 and R ^d1 may be combined to form a divalent organic group.
Examples of the divalent organic group that can be formed include a substituted or unsubstituted C2-5 alkylene group or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group.
Examples of the "C2-5 alkylene group" include dimethylene group, trimethylene group, and tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; methyl group, ethyl group, n - C1-6 alkyl group 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, and 1-fluoro-n-butyl group are preferred.

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

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-mentioned "group represented by R ^c1 R ^d1 N-".
Specific examples of "group represented by R ^c1 R ^d1 N-CO-" include carbamoyl group, N,N-dimethylaminocarbonyl group, N-(i-propyl)aminocarbonyl group, N-(i-propyl )-N-methylaminocarbonyl group and the like.

In the "group represented by R ^a1 -CO-O-" in Ga, R ^a1 has the same meaning as in the above-mentioned "group represented by R ^a1 -CO-".
A specific example of "the group represented by R ^a1 --CO--O-" includes an acetyloxy group.

In the "group represented by R ^a1 --CO-NR ^e1 --" in Ga, R ^a1 has the same meaning as in the above-mentioned "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 include the same ones as exemplified for R ^a1 .
A specific example of "the group represented by R ^a1 --CO-NR ^e1 --" includes an acetylamino group.

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

In the "group represented by R ^b1 --O-CO-NR ^e1 --" in Ga, R ^b1 has the same meaning as in the above-mentioned "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 —”.
A specific example of "the group represented by R ^b1 --O-CO-NR ^e1 --" includes a methoxycarbonylamino group.

In the "group represented by R ^c1 R ^d1 N-CO-O-" in 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 "a group represented by R ^c1 R ^d1 N-CO-O-" include a carbamoyloxy group, an N,N-dimethylaminocarbonyloxy group, and the like.

In the "group represented by R ^c1 R ^d1 N-CO-NR ^e1 -" in 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 --" 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 --".
A specific example of "the group represented by R ^b1 SO ₂ --NR ^e1 --" includes a methanesulfonylamino group.

In the "group represented by R ^c1 R ^d1 N--SO ₂ --" in Ga, R ^c1 and R ^d1 have the same meanings as in the above-mentioned "group represented by R ^c1 R ^d1 N-".
A specific example of the "group represented by R ^c1 R ^d1 N-SO ₂ -" includes an N,N-dimethylaminosulfonyl group.

In the "group represented by R ^a1 O-N=CR ^f1 -" in Ga, R ^a1 has the same meaning as in the above-mentioned "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 R ^a .
Specific examples of "the group represented by R ^a1 O-N=CR ^f1 -" include (hydroxyimino)methyl group, (ethoxyimino)methyl group, and the like.

In the "group represented by R ^g1 R ^h1 C=N-O-" in Ga, R ^g1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted C2-6 alkenyl group. 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 5-6 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 can be the same as those exemplified for R ^a1 .
Here, R ^g1 and R ^h1 may form a divalent organic group together.
Examples of the divalent organic group that can be formed include a substituted or unsubstituted C2-5 alkylene group or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group.
Examples of the "C2-5 alkylene group" include dimethylene group, trimethylene group, and tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; methyl group, ethyl group, n - C1-6 alkyl group 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, and 1-fluoro-n-butyl group are preferred.
A specific example of "a group represented by R ^g1 R ^h1 C=N--O-" includes a (propan-2-ylideneamino)oxy group.

In the "divalent group represented by R ^a1 --N=" in 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=), a methylimino group, and the like.

In the "divalent group represented by R ^a1 O--N=" in Ga, R ^a1 has the same meaning as in the above-mentioned "group represented by R ^a1 -CO-".
Specific examples of "the divalent group represented by R ^a1 O--N=" include N-hydroxyimino group, N-methoxyimino group, and the like.

In the "divalent group represented by R ^c1 R ^d1 NN=" in Ga, R ^c1 and R ^d1 have the same meanings as in the above "group represented by R ^c1 R ^d1 N-". show.
A specific example of the "divalent group represented by R ^c1 R ^d1 NN=" includes 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=" in Ga, R ^b1 has the same meaning as that in the above "group represented by R ^b1 -O-CO-" shows. 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 groups that can be formed by combining two of them include a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxyC1-4 Examples include an alkylene group, a substituted or unsubstituted oxyC2-3 alkyleneoxy group, and a substituted or unsubstituted C1-3 alkyleneoxyC1-3 alkylene group.
Examples of the "C1-5 alkylene group" include methylene group, dimethylene group, trimethylene group, and tetramethylene group.
Examples of the "oxy C1-4 alkylene group" include oxymethylene group and oxydimethylene group.
Examples of the "oxyC2-3 alkyleneoxy group" include an oxydimethyleneoxy group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on "C1-5 alkylene group", "oxyC1-4 alkylene group", "oxyC2-3 alkyleneoxy group", "C1-3 alkyleneoxy C1-3 alkylene group" include fluoro group, chloro C1 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, etc. -6 alkyl group; or C1-6 haloalkyl group such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, etc. are preferred.

In the present invention, preferred examples of Ga include 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 C2-6 alkynyloxy group, and a substituted or unsubstituted C2-6 alkynyloxy group. C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, group represented by R ^a1 -CO-O-, oxo A divalent group represented by a group (O=) or R ^a1 O--N= can be mentioned.
In this case, a preferred substituted or unsubstituted 5- to 6-membered heterocyclyloxy group includes a tetrahydro-2H-pyran-4-yl group.

In the present invention, more preferable Ga is 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 - Examples include a group represented by CO-O-, an oxo group (O=), and a divalent group represented by R ^a1 O-N=.

[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" in Q include phenyl group, naphthyl group, indenyl group, indanyl group, and tetralinyl group.

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

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

Substituents on the "C6-10 aryl group" or "5-10 membered heterocyclyl group" in Q include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; methyl group, 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; 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, etc. 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 - TriC1-6 alkyl-substituted silyloxy C1-6 alkoxy groups such as butyldimethylsilyloxyethoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy groups, 2,3-dichlorobutoxy groups, trifluoromethoxy groups, etc. 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 alkoxy group) C1-6 alkoxy group; 5-membered heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, 5-membered heteroaryl substituted with one or more substituents of halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkoxy group; 6-membered heteroaryl C1-6 Alkoxy group; (6-membered heteroaryl substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) ) C1-6 alkoxy group; C1-6 alkylthio group such as methylthio group and ethylthio group; C1-6 alkylsulfinyl group such as methylsulfinyl group and ethylsulfinyl group; C1-6 alkylsulfonyl group such as methylsulfonyl group and ethylsulfonyl group Group: C1-6 haloalkylthio group such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group: C1-6 haloalkyl group such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group Sulfinyl group; C1-6 haloalkylsulfonyl group such as trifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group; C3-6 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group; C1-6 C3-6 cycloalkyl group substituted with one or more substituents of an alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; cyclopropenyl C3-6 cycloalkenyl groups such as cyclobutenyl group, cyclopentenyl group; C6-10 aryl groups such as phenyl group, naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-fluoro C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group such as phenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group C6-10 aryl group substituted with one or more substituents; 3- to 4-membered saturated heterocyclyl group such as aziridinyl group, epoxy group, azetidinyl group, oxetanyl group; C1-6 alkyl group, C1-6 alkoxy a 3- to 4-membered saturated heterocyclyl group substituted with one or more substituents of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, 5- to 6-membered saturated heterocyclyl group such as tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 A 5- to 6-membered saturated heterocyclyl group substituted with one or more substituents of a 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 group, tetrazolyl group, etc. 5-membered heteroaryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group , or a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. Aryl group; 6-membered heteroaryl group substituted with one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group ; 5-membered ring partially unsaturated heterocyclyl group such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a 5-membered ring partially saturated heterocyclyl group substituted with one or more substituents of a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered ring partially unsaturated heterocyclyl group such as a dihydropyranyl group ; a 6-membered partially saturated heterocyclyl group substituted with 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;
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, A 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 C1-10 aryl substituted with one or more substituents of haloalkyl group or C1-6 haloalkoxy group) C1-6 alkyl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 ~5- to 6-membered heteroaryl substituted with one or more substituents of ~6 haloalkyl group or 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 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 A C6-10 aryl group substituted with any one or more substituents of a C1-6 haloalkoxy group; a 5- to 6-membered heteroaryl group; or; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group , a 5- to 6-membered heteroaryl group substituted with one or more substituents of 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; halogeno group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, 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 group) (C1-6 alkyl group, C1-6 alkyl group, C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 aryl substituted with one or more substituents of C1-6 haloalkoxy group) 5- to 6-membered heteroaryl substituted with one or more substituents of 6-haloalkyl group or 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 A C3-6 cycloalkyl group substituted with 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 a C1-6 haloalkoxy group C6-10 aryl group substituted with one or more substituents; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1 ~ 6 A 5- to 6-membered heteroaryl group substituted with one or more substituents of haloalkoxy groups; 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 form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group);
R ^Q1 R ^Q1 A group represented by N-CO- (R ^Q1 in the formula may be the same or different. R ^Q1 together represent a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyl may form a methyleneoxydimethylene group);
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 a C1-6 alkyl group substituted with one or more substituents of a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- to 6-membered heteroaryl group; a C6-10 aryl) C1-6 alkyl group substituted with 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; or (5- to 6-membered heteroaryl substituted with 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) Indicates a C1-6 alkyl group; the same applies to R ^Q3 below);
R ^Q2 -O-CO-O-; R ^Q2 -O-CO-NR ^Q3 -; R ^Q1 R ^Q1 N-CO-O- (in the formula R ^Q1 may be the same or different. R ^Q1 may be taken together 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 - (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 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. R ^Q1 may be taken together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
A group represented by R ^Q1 -O-N=C(R ^Q4 )- (wherein R ^Q4 represents a hydrogen atom or a C1-6 alkyl group); (R ^Q1 ) ₂ C=N-O- A group represented by (R ^Q1 in the formula may be the same or different. R ^Q1 together form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group) );
A pentafluorosulfanyl group, a trimethylsilylethynyl group, a nitro group, or a cyano group is preferred.
Furthermore, as a substituent on the "5- to 10-membered heterocyclyl group", an oxo group is also preferred.

〔salt〕
The salt of compound (I) is not particularly limited as long as it is acceptable for agricultural, horticultural, medical, or animal use. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium and magnesium; iron, copper, etc. 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. Moreover, the salt of compound (I) can be obtained from compound (I) by a known method.

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

The agricultural and horticultural fungicides of the present invention can be applied to a wide range of types of filamentous fungi, such as Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and zygomycetes. It can be used to control plant diseases caused by fungi belonging to the fungi (Zygomycetes).

Examples of plant diseases (pathogens) that can be controlled are shown below.
Sugar beet: Cercospora beticola, Aphanomyces cochlioides, Root rot (Thananatephorus cucumeris), Leaf rot (Thananatephorus cucumeris), Rust (Uromyces betae), Powdery mildew (Oidium sp.), Spot disease (Ramularia beticola), Seedling damping off (Aphanomycescochlioides, Pythium ultimum), etc. Groundnut: brown spot (Mycosphaerella arachidis), stain disease (Ascochyta sp.), rust (Puccinia arachidis), damping off (Pythium debaryanum), etc. Rust spot (Alternaria alternata), white silk disease (Sclerotium rolfsii), black astringent disease (Mycosphaerella berkeleyi), black root rot (Calonectriailicicola), etc. Cucumber: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerellamelonis), Fusarium oxysporum, Sclerotinia sclerotiorum, Botrytiscinerea, Colletotrichum orbiculare, Cladosporium cucumerinum, Corynesporacassiicola, seedlings Damping-off (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis sp., bacterial spot (Pseudomonas syringae pv. Lachrymans), etc. Tomato: Botrytis cinerea, leaf mold (Cladosporium fulvum), late blight (Phytophthorainfestans), Verticillium albo-atrum, Verticillium dahliae, Powdery mildew (Oidiumneolycopersici), Alternaria solani, Pseudocercospora fuligena, Bacterial wilt (Ralstoniasolanacearum), Sclerotinia (Sclerotinia sclerotiorum) etc. Eggplant: Botrytis cinerea, black blight (Corynespora melongenae), powdery mildew (Erysiphecichoracearum), sooty mold (Mycovellosiella nattrassii), sclerotia (Sclerotinia sclerotiorum), half-wilt ( Verticillium dahliae), Phomopsis vexans, etc. Capsicum: Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, Anthrax (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), Udon Strawberry: Botrytis cinerea, powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichumacutatum, Colletotrichum fragariae), late blight (Phytophthora cactorum), soft rot (Rhizopusstolonifer), yellow blight ( Onions: Botrytis allii, Botrytis cinerea, Botrytis squamosa, Peronospora, etc. destructor), white late blight (Phytophthoraporri), microsclerotinia (Ciborinia allii), microsclerotia rot (Botrytis squamosa), dry rot (Fusarium oxysporum), red root rot (Pyrenochaeta terrestris), black rot sclerotia (Sclerotium cepivorum), rust (Puccinia allii), white silk rot (Sclerotium rolfsii), etc. Allium: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black rot sclerotium ( Sclerotium cepivorum), rust (Puccinia allii), white spot leaf blight (Botrytis squamosa), white silk disease (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc. Cabbage: Club club disease (Plasmodiophora brassicae), soft rot ( Erwinia carotovora), black rot (Xanthomonascampesrtis pv. campestris), bacterial black spot (Pseudomonas syringaepv. maculicola, P. s. pv. alisalensis), downy mildew (Peronospora parasitica), sclerotinias sclerotiorum, black soot Lettuce: Lettuce: Pseudomonas cichorii, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremialactucae), gray mold (Botrytis cinerea), sclerotinia sclerotiorum, big-vein disease (Mirafiori lettucebig-vein ophiovirus), root rot (Fusarium oxysporum) ), Rhizoctonia solani, powdery mildew (Golovinomycesorontii), etc. Green beans: Sclerotinia sclerotiorum, Botrytis cinerea, anthracnose (Colletotrichumlindemuthianum), horn spot (Phaeoisariopsis griseola), etc. Peas : Mycosphaerella blight, Botrytis cinerea, Sclerotinia sclerotiorum, Erysiphe pisi, etc.

Apples: Powdery mildew (Podosphaera leucotricha), Venturia inaequalis, Monilinia mali, Mycosphaerella pomi, Valsa mali, Alternaria mali, Gymnosporangium yamadae), Botryosphaeria berengeriana, Anthracnose (Glomerellacingulata, Colletotrichum acutatum), Diplocarpon mali, Zygophialajamaicensis, Gloeodes pomigena, Helicobasidium Mompa), Rosellinianecatrix, Botrytis cinerea, Erwinia amylovora, Chondrostereumpurpureum, Rhizobium radiobacter, Rhizobium rhizogenes, etc. Plum: Black star Diseases such as Cladosporium carpophilum, Botrytis cinerea, Monilinia mumecola, Peltaster sp., Taphrina pruni, Phloeosporella padi, etc. Oysters: Udon Phyllactinia kakicola, anthracnose (Gloeosporium kaki), Cercospora kaki, Mycosphaerella nawae, Botrytis cinerea, soot spot (Zygophiala jamaicensis), etc. : Monilinia fructicola, Moniliafructigena, Cladosporium carpophilum, Phomopsis sp., Xanthomonas campestrispv. pruni, Taphrina deformans, Colletotrichum gloeosporioides ), Phloeosporellapadi, Coriolus versicolor
Almond: Monilinia laxa, Stigminacarpophila, Cladosporium carpophilum, Polystigma rubrum, Alternaria alternata, Colletotrichum gloeospoides, etc. Hawthorn: Gray Star disease (Monilinia fructicola), anthracnose (Colletotrichum acutatum), black spot (Alternaria sp.), young fruit sclerotia (Monilinia kusanoi), brown borer disease (Mycosphaerellacerasella), powdery mildew (Podosphaera tridactyla), etc. Grape : Botrytis cinerea, powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmoparaviticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis) , Black rot (Guignardia bidwellii), White rot (Coniella castaneicola), Rust (Phakopsora ampelopsidis), White cotton snow disease (pathogen unidentified), Rhizobium radiobacter, Rhizobium vitis, etc. Pear: Black rot (Venturia nashicola), Gymnosporangium asiaticum, black spot (Alternariakikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), body blight (Phomopsis fukushii), brown spot (Stemphylium vesicarium) , anthracnose (Glomerellacingulata), etc. Tea: Pestalotiopsis longiseta (P. Citrus: Elsinoe fawcettii, Penicillium italicum, Penicillium digitatum, Botrytis cinerea, Diaporthe citri, Xanthomonascampestris pv.Citri ), powdery mildew (Oidium sp.), late blight (Phytophthora citrophthora), anthracnose (Colletotrichumfioriniae), etc. Kiwifruit: bacterial flower rot disease (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker disease (Pseudomonas syringae), gray Mildew (Botrytis cinerea), fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty spot (Pseudocercosporaactinidiae), etc. Olive: Anthracnose (Colletotrichum acutatum, Colletotrichumgloeosporioides), Peacock spot (Spilocaeaoleaginea), etc. Chestnut: Anthrax (Colletotrichum gloeosporioides) etc.

Wheat: Powdery mildew (Blumeria graminis f.sp. tritici), Fusarium head rust (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), Fusarium rust (Puccinia recondita), Yellow rust (Puccinia striiformis), Brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eye spot disease (Pseudocercosporellaherpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow rot small-grain sclerotium (Typhulaincarnata) , 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: spotted leaf disease (Pyrenophora graminea), net spot disease (Pyrenophora teres), cloud shape (Rhynchosporium secalis), naked smut (Ustilago tritici, U.nuda), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. : Blast (Pyricularia oryzae), Sheath blight (Rhizoctonia solani), Gibberella fujikuroi, Sesame leaf blight (Cochliobolus miyabeanus), Seedling damping off (Pythium graminicola), White leaf blight (Xanthomonas oryzae), Seedlings Burkholderia plantarii, Acidovorax avenae, Burkholderia glumae, Cercospora oryzae, Ustilaginoidea virens, Alternaria alternata, Curvularia intermedia , Alternaria padwickii, Epicoccum purpurascens, etc. Tobacco: Sclerotinia sclerotiorum, Erysiphe cichoracearum, Phytophthoranicotianae, etc. Tulip: Botrytis cinerea, brown Spot disease (Botrytis tulipae), leaf rot (Rhizoctonia solani), bulb rot (Fusarium oxysporum), skin rot (Rhizoctonia solani), etc. Roses: Diplocarpon rosae, powdery mildew (Erysiphe simulans, Podosphaera pannosa) , Botrytis cinerea, etc. Chrysanthemum: Botrytis cinerea, white rust (Puccinia horiana), downy mildew (Paraperonospora minor, Peronospora danica), Pythium damping off (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), damping off (Rhizoctonia solani), Fusarium solani, etc. Gerberas: Botrytis cinerea, powdery mildew (Podosphaera xanthii), etc. Lilies: Leaf blight ( Botrytis elliptica, Pestalotiopsis sp.), Botrytis cinerea, etc. Sunflower: Downy mildew (Plasmopara halstedii), Sclerotinia sclerotiorum, Botrytis cinerea, etc. Bentgrass: Snow rot large-grain sclerotia ( Sclerotinia borealis), large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), red burn (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola), etc. Orchardgrass : Powdery mildew (Erysiphe graminis), etc. Soybean: Purpura (Cercospora kikuchii), Downy mildew (Peronospora manshurica), Stem blight (Phytophthorasojae), Rust (Phakopsora pachyrhizi), Sclerotinia sclerotiorum, Anthracnose (Colletotrichum truncatum), Botrytis cinerea, Elsinoe glycines, Black spot (Diaporthe phaseolorumvar. sojae), Damping off (Pythiumspp., Fusarium spp., Rhizoctoniaspp.), Seedling blight (Pythiumspp., Fusarium spp., Rhizoctoniaspp.), etc. Potatoes: Late blight (Phytophthora infestans), summer blight (Alternaria solani), black bruise (Thanaphorus cucumeris), half-wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), black leg blight (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytiscinerea), scab (Streptomyces spp.), sclerotinia (Sclerotinia sclerotiorum), etc. Dioscorea: Leaf astringent disease (Cylindrosporium dioscoreae), anthracnose (Colletotrichum) gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Sweet potato: Helicobasidium mompa, vine rot (Fusarium oxysporum), etc. Taro: Late blight (Phytophthora colocasiae), stem rot (Rhizoctonia solani), etc. Ginger: Rhizoctonia solani ( Pythium ultimum, Pythiummyriotylum), Phyllosticta zingiberis, etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum aenigma), Canker disease (Xanthomonas campestris), Axial rot (Diaporthepseudophoenicicola, 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 (Colletotrichum coffeanum), brown eye disease (Cercosporacoffeicola), etc. Sugarcane: Brown rust (Puccinia melanocephala), etc. Corn: Gloeocercospora sorghi, rust (Puccinia sorghi), southern rust (Puccinia polysora), smut (Ustilago maydis), sesame leaf blight (Cochliobolus heterostrophus), soot Seedling blight (Setosphaeria turcica), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusariumspp., Rhizoctonia spp.), etc. Cotton: Seedling blight (Pythium sp.), Rust (Phakopsoragossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hops: downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea) Such

[Nematicide]
The pyridazinone compound of the present invention also has an excellent control effect on various nematodes that affect plant growth.
The nematicide of the present invention contains at least one selected from compound (I) and its salt as an active ingredient. The amount of compound (I) or its salt contained in the nematocide of the present invention is not particularly limited as long as it exhibits a nematode controlling 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) Of the Anguinidae family, for example, Anguina spp., Anguina funesta, Anguina tritici; Ditylenchus spp., Ditylenchus spp. Ditylenchus destructor), Ditylenchus dipsaci, mushroom nematode (Ditylenchus myceliophagus);
(b) Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi of the family Aphelenchoideidae, such as Aphelenchoides spp.; Bursaphelenchus xylophilus, a species of the genus Bursaphelenchuspp.;
(c) Belonolaimus longicaudatus of the family Belonolaimidae, for example Belonolaimus spp.; Tylenchorhynchus claytoni of the genus Tylenchorhynchus spp.; Tylenchorhynchus dubius;
(d) of the family Criconematidae, such as Criconema mutabile;
(e) Dolichodoridae, for example Dolichodorus mediterraneus;
(f) Ecphyadophoridae, e.g. Ecphyadophora tenuissima
(g) Hemicycliophoridae, for example, Loofia thienemanni;
(h) Potato cyst nematode (Globoderarostochiensis), potato cyst nematode (Globodera pallida), tobacco cyst nematode (Globodera tabacum) of Heteroderidae, such as Globodera spp.; Heterodera spp. Heterodera spp.), wheat cyst nematode (Heterodera avenae), Heterodera cruciferae (Heterodera cruciferae), soybean cyst nematode (Heterodera glycines), sugar beet cyst nematode (Heterodera schachtii), clover cyst nematode (Heterodera trifolii);
(i) Hoplolaimidae, such as Helicotylenchus spp., Helicotylenchus dihystera, Helicotylenchus multicinctus; Hoplolaimus spp., Hoplolaimus columbus ( Hoplolaimus columbus, Hoplolaimus galeatus; other, Rotylenchus robustus, Rotylenchulus reniformis;
(j) Meloidogynidae, such as Meloidogynespp., Meloidogynearenaria, Meloidogyne chitwoodi, Meloidogyne hapla, Meloidogyneincognita, Javanese (Meloidogyne javanica), Thames Nematode (Meloidogyne thamesi);
(k) Nothotylenchidae, for example, Nothotylenchus acris;
(l) Paratylenchus curvitatus, Paratylenchus elachistus, of the Paratylenchus family, such as Paratylenchus spp.;
(m) Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus of the Pratylenchus spp. species of the family Pratylenchidae; Pratylenchus fallax, Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Pratylenchus scribneri, Pratylenchus goodeyi Pratylenchus vulnus), Pratylenchuszeae; others, Nacobbus aberrans, Radopholus similis, Tylenchulussemipenetrans, Radopholus citrophilus.

(2) Dorylaimida
(a) Of the family Longidoridae, for example Longidorus spp., Longidoruselongates; of the genus Xiphinema, Xiphinema americanum, Xiphinema brevicore ( Xiphinema brevicolle), Xiphinema index (Xiphinema index), Xiphinema diversicaudatum (Xiphinema diversicaudatum).

(3) Triplonchida (Triplonchida)
(a) Trichodoridae, such as Trichodorus primitivus and Paratrichodorusminor.

[Application method/mixture]
The agricultural and horticultural fungicide or nematicide of the present invention is suitable for crops such as grains; vegetables; root vegetables; tubers; trees such as fruit trees, tea, coffee, and cacao; grasses; turf; plants such as cotton; It is preferable to use it for.

The agricultural and horticultural fungicide of the present invention can be applied to various parts of plants, such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, roots, shoots, and cuttings. . Nematicides can be applied to roots, tubers, tuberous roots, etc. Furthermore, improved varieties/variants, cultivated varieties, mutants, hybrids, and genetically modified plants (GMOs) of these plants can also be targeted.

The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage spraying, soil application, water surface application, etc. to control various diseases that occur in agricultural and horticultural crops including flowers, lawns, and grasses. I can do it. Nematicides can be used for seed treatment, soil application, etc.

The agricultural and horticultural fungicide or nematicide of the present invention may contain components other than the pyridazinone compound of the present invention. Other components include known carriers used for formulation. In addition, other ingredients include conventionally known fungicides, insecticides/acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil conditioners, animal feed, etc. be able to. By containing such other components, a synergistic effect may be produced.
That is, one aspect of the present invention can include an agricultural and horticultural fungicide that includes one or more additional fungicides.

Specific examples of fungicides that can be mixed or used in combination with the agricultural and horticultural fungicides or nematicides of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitor:
(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furaraxyl, metalaxyl, metalaxyl-M; oxadixyl; clodiracon, offrace;
(b) adenosine deaminase inhibitors: bupirimate, dimethylimole, ethyrimol;
(c) DNA/RNA synthesis inhibitor: hymexazole, octylinone;
(d) DNA topoisomerase II inhibitor: oxolinic acid.

(2) Mitotic inhibitors and cell division inhibitors:
(a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorfenazole, fubelidazole, thiabendazole; thiophanate, thiophanate methyl; diethofencarb; zoxamide; ethaboxam;
(b) Cell division inhibitor: Pencyclone;
(c) Delocalized inhibitors of spectrin-like proteins: fluopicolide, fluopimomide.

(3) Respiratory inhibitors:
(a) Complex I-NADH oxidoreductase inhibitor: diflumetrim; tolfenpyrad;
(b) Complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil; isofetamide; fluopyram; fenflam, flumesicrox; carboxin, oxycarboxin; thifluzamide; benzobine diflupyr, bixafen, fluxapirox Sado, furametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid, pidiflumethofen, isoflucipram, pyradiflumide, inpyrfluxam;
(c) Complex III-ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin , pyrametostrobin, triclopiricarb; cresoxime-methyl, trifloxystrobin; dimoxystrobin, phenaminestrobin, metominostrobin, orisastrobin; famoxadone; fluoxastrobin; fenamidon; pyribencarb; methyltetraprole; Destrobin;
(d) Complex III-ubiquinol reductase Qi inhibitor: Cyazofamid; Amisulbrome; Fenpicoxamide;
(e) Uncoupler of oxidative phosphorylation: binapacryl, meptyldinocap, dinocap; fluazinam; felimzone;
(f) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(g) ATP production inhibitor: silthiopham;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): ametoctrazine.

(4) Amino acid and protein synthesis inhibitors:
(a) Methionine biosynthesis inhibitors: Andoprim, cyprodinil, mepanipirim, pyrimethanil;
(b) Protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.

(5) Signal transduction inhibitor:
(a) Signal transduction inhibitors: quinoxyfen, proquinazide;
(b) MAP histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil; clozolinate, iprodione, procymidone, vinclozolin.

(6) Lipid and cell membrane synthesis inhibitors:
(a) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos; isoprothiolane;
(b) Lipid peroxidants: biphenyl, chloroneb, dichlorane, quintozene, tecnazene, tolclofos-methyl; etridiazole;
(c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbu fostylate, prothiocarb.

(7) Cell membrane sterol biosynthesis inhibitor:
(a) Demethylation inhibitors at C14 position in sterol biosynthesis: triforine; pyrifenox, pyrisoxazole; fenarimol, flurprimidol, nuarimol; imazalil, imazalil sulfate, oxpoconazole, pefrazoate, prochloraz, triflumizole , biniconazole; azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole, mefene trifluconazole;
(b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperaline; spiroxamine;
(c) 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis system: fenhexamide; fenpyrazamine;
(d) Squalene epoxidase inhibitor of sterol biosynthesis system: pyributicarb; naftifine, terbinafine.

(8) Cell wall synthesis inhibitor:
(a) Trehalase inhibitor: validamycin;
(b) Chitin synthase inhibitor: polyoxin, polyoxolim;
(c) Cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph; bentiavaricarb, iprovaricarb, variphenarate; mandipropamide.

(9) Melanin biosynthesis inhibitors (a) Melanin biosynthesis reductase inhibitors: fusaride; pyroquilone; tricyclazole;
(b) Dehydratase inhibitors of melanin biosynthesis: carpropamide; diclosimet; phenoxanil;
(c) Polyketide synthesis inhibitor of melanin biosynthesis: tolprocarb.

(10) Host plant resistance inducer:
(a) Agent acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: probenazole, tiadinil, isotianil, dichlorbenziazox, ipfentrifluconazole, laminarin, Japanese knotweed extract.

(11) Agents with unknown activity: cymoxanil, fosetylaluminum, phosphoric acid (phosphate), tecroftalam, triazoxide, fursulfamide, diclomedine, metasulfocarb, cyflufenamide, metraphenone, pyriophenone, dodine, dodine free base, flutianil.

(12) Agents with multiple sites of action: copper (copper salts), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; furbam, mancozeb, maneb, Mannkappa, methiram, polycarbamate, propineb, thiram, zineb, ziram; captan, captafol, folpet; chlorothalonil; dichlorofluanid, tolylfluanid; guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine albe Silate (iminoctadinetrialbesilate); Anilazine; Dithianone; Chinomethionate; Fluorimide.

(13) Other agents: DBEDC, fluorophorpet, bis(8-quinolinolato)copper (II), propamidine, chloropicrin, ciproflam, agrobacterium, betoxazine, diphenylamine, methyl isocyanate (MITC), mildeomycin , capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methyl sulfonate, flumetover, fosetyl calcium, fosetyl sodium, ilmamycin, natamycin, nitrotal isopropyl, oxamocarb, pyrrole nitri Tebufloquine, Tolnifanide, Zalilamide, Algophase, Amicarthiazol, Oxathiapiprolin, Fluoxapiprolin, Methiram Zinc, Bentiazole, Triclamide, Uniconazole, Oxyfenthiin (Oxyfenthiin), Picarbutrazox, Quinofumelin, Florylpicoxamide, Pyrapropoyne, Fluindapyr, Aminopyrifen, Pyridachlomethyl, Ipflufenoquin, dipimethitron.
(14) Biopesticides/biologically derived pesticides with multiple mechanisms of action: extract from the cotyledons of lupine plantlets; extract from Swinglea glutinosa; extract from Swinglea glutinosa; extract from Melaleuca alternifolia (tea tree oil); plant oils (mixtures): eugenol, geraniol, thymol.
(15) Biological pesticides/biologically derived pesticides with multiple mechanisms of action: Trichoderma atroviride strain I-1237, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1 (Trichoderma atroviride strain SC1), Trichoderma atroviride strain SKT-1 (Trichoderma atroviride strain SKT-1), Trichoderma atroviride strain 77B (Trichoderma atroviride strain 77B);
Trichoderma asperellum strain T34, Trichoderma asperellum strain kd;
Trichoderma harzianum strain T-22;
Trichoderma virens strain G-41;
Gliocladium catenulatum strain J1446; Clonostachys rosea strain CR-7;
Coniothyrium minitans strain CON/M/91-08;
Talaromyces flavus strain SAY-Y-94-01;
Saccharomyces cerevisae strain LAS02;
Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens D 747 Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332;
Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis strain HAI-0404;
Pseudomonas chlororaphis strain AFS009;
Streptomyces griseovirides strain K61;
Streptomyces lydicus strain WYEC108.

Specific examples of insecticides/acaricides, nematicides, soil insecticides, anthelmintic agents, etc. that can be mixed or used in combination with the agricultural and horticultural fungicides or nematicides of the present invention are shown below.
(1A) Acetylcholinesterase (AChE) inhibitor (carbamate type):
Aranicarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, Thiophanox, triazamate, trimetacarb, XMC, xylylcarb.

(1B) Acetylcholinesterase (AChE) inhibitor (organophosphorus):
Acephate, azamethyphos, azinphos ethyl, azinphos methyl, cassafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos methyl, coumafos, cyanophos, dimeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, Ethion, ethoprofos, fanflu, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenofos, imisiafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, nared, Omethoate, oxydimethone methyl, parathion, parathion methyl, phenthoate, phorate, fosalone, phosmet, phosphamidon, phoxim, pirimiphos methyl, profenofos, propetamfos, prothiofos, pyraclofos, pyridafenthione, quinalfos, sulfotep, tebupirimphos, temefos, terbufos, tetrachlorvinfos, Thiometone, triazophos, trichlorfon, vamidothione.

(2) GABAergic chloride ion (chloride ion) channel blocker:
Chlordane, endosulfan; ethiprole, fipronil.
Flufiprol.
(3A) Sodium channel modulator (pyrethroid):
Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ- Cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-( 1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halfenprox, imiprithrine, cadethrin, permethrin, phenothrin [(1R)-trans isomer], pralethrin, pyrethrin, resmethrin, cilafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin.
κ-bifenthrin, chloroprarethrin, heptafluthrin, meperfluthrin, ε-methofluthrin, monfluorothrin, ε-monfluorothrin, κ-tefluthrin, tetramethylfluthrin; bioethanomethrin. (3B) Sodium channel modulators (DDTs):
DDT, methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulator:
Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; nicotine; sulfoxaflor; flupyradifurone; triflumezopyrim.
Dichloromesothiaz, flupyrimine.
(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulator:
spinetoram, spinosad.
(6) Glutamatergic chloride channel (GluCl) allosteric modulator:
Abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin.
Doramectin, eprinomectin, ivermectin, moxidectin, selamectin. (7) Juvenile hormone analogues:
Hydroprene, quinoprene, methoprene; phenoxycarb; pyriproxyfen.
(8) Other non-specific (multisite) inhibitors:
Methyl bromide, alkyl halides; chloropicrin; sodium aluminum fluoride, sulfuryl fluoride; borax, boric acid, disodium octaborate, sodium borate, sodium metaborate; tartar; dazomet, metam, Metam potassium salt, metam sodium salt.
(9) Chord tone organ TRPV channel modulator:
Pimetrozine, pyrifluquinazone; afidopyropene.

(10) Mite growth inhibitor:
Clofentezine, diflobidazine, hexythiazox; etoxazole.
(11) Microbial-derived insect midgut lining disrupting agent:
Bt subsp. Bacillus sphaericus.
(12) Mitochondrial ATP synthase inhibitor:
Diafenthiuron; azocyclotine, cyhexatin, fenbutastin oxide; propargite; tetradifon.
(13) Oxidative phosphorylation uncoupler that disrupts the proton gradient:
Chlorfenapyr, DNOC, Sulflumide.
(14) Nicotinic acetylcholine receptor (nAChR) channel blocker:
Bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt. (15) Chitin biosynthesis inhibitor, type 0:
Bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.
(16) Chitin biosynthesis inhibitor, type 1:
Buprofezin.
(17) Molting inhibitor:
Cyromazin.
(18) Molting hormone (ecdysone) receptor agonist:
Chromafenozide, halofenozide, methoxyfenozide, tebufenozide.
(19) Octopamine receptor agonist:
Amitraz.

(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-dependent sodium channel blocker:
Indoxacarb; metaflumizone.
(23) Acetyl CoA carboxylase inhibitor:
spirodiclofen, spiromesifen, spirotetramate.
Spiropidion.
(24) Mitochondrial electron transport chain complex IV inhibitor:
Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine; calcium cyanide, sodium cyanide, potassium cyanide.
(25) Mitochondrial electron transport chain complex II inhibitor:
Cyenopyrafen, cyflumetofen; pyflubumide.
(28) Ryanodine receptor modulator:
Chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide.
Cyhalodiamide, Tetrachlorantraniliprole, Tetraniliprole.
(29) Chord-tone organ modulator Target site unspecified:
flonicamid.
(30) GABAergic chloride ion (chloride ion) channel allosteric modulator:
Broflanilide, fluxamethamide.
Isocycloceram; Afoxolaner, fluralaner, rotineral, sarolaner.
Other insecticides and acaricides:
Azadirachtin, benzoximate, bromopropylate, chinomethionate, dicofol, lime-sulfur mixture, mancozeb, pyridalyl, sulfur.
Acinonapyr, benzpyrimoxane, flometoquine, fluhexafone, oxazosulfil, ticlopyrazofurol.

Dewormer:
(a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netovimine, thiophanate; thiabendazole, cambendazole;
(b) Salicylanilide series: closantel, oxyclozanide, lafoxanide, niclosamide;
(c) Substituted phenolics: nitroxynil, nitrossucanate;
(d) Pyrimidine series: pyrantel, morantel;
(e) Imidazothiazole series: levamisole, tetramisole;
(f) Tetrahydropyrimidine series: praziquantel, epciprantel;
(g) Other anthelmintics: cyclodiene, riania, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetalsamide, melarsomine, arsenamide.

Specific examples of plant regulators that can be mixed or used in combination with the agricultural and horticultural fungicides or nematicides of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as aviglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 - Naphthylacetamide, etyclozate, chloroxyfonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+) -deoxystrigol, (+)-olobanchol, (+)-solgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid; ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid.

[Prescription]
The agricultural and horticultural fungicide or nematicide of the present invention contains, in addition to the pyridazinone compound of the present invention, other active ingredients and agriculturally and horticulturally acceptable auxiliary ingredients (for example, 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. Examples include dosage forms such as wettable powders, emulsions, powders, granules, aqueous solutions, suspensions, wettable powders, and tablets. There are no particular restrictions on the preparation method for the preparation, and known preparation methods can be employed depending on the dosage form.
Some formulation examples are shown below. The formulation formulations shown below are merely examples and can be modified within the scope of the invention, and the invention is not limited in any way by the formulation examples below. "Part" means "part by weight" unless otherwise specified.

(Formulation example 1: hydrating 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 ground 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 alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the 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 mixed uniformly, finely ground, and then granulated to a particle diameter of 0.5 to 1.0 mm. to obtain granules containing 5% of the active ingredient.
(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 dioctyl sulfosuccinate sodium salt and 1 part of potassium phosphate were uniformly mixed and pulverized. Water is added to the mixture and kneaded well, followed by granulation and drying 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 alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water were mixed to a particle size of 3 microns or less. The suspension was wet-milled until a suspension containing 10% of the active ingredient was obtained.
(Formulation example 6: hydrated granules)
40 parts of the pyridazinone compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of alkylbenzenesulfonic acid sodium salt, 8 parts of ligninsulfonic acid sodium salt, and 5 parts of the formaldehyde condensate of the alkylbenzenesulfonic acid sodium salt are uniformly mixed. After grinding it finely, add an appropriate amount of water and knead it into a clay-like consistency. The clay-like material is granulated and then dried to obtain a granular wettable powder containing 40% of the active ingredient.

[Medical/animal (veterinary) antifungal agent]
The pyridazinone compound of the present invention can be used as a prophylactic or therapeutic agent for controlling harmful pathogenic bacteria, 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 its salt as an active ingredient. The amount of compound (I) or its salt contained in the medical antifungal agent of the present invention is not particularly limited as long as it exhibits an antifungal effect.

In this specification, "animal" refers to vertebrate animals such as pet animals, livestock/poultry, exhibition animals kept in zoos and aquariums, captured wild animals, and research/experimental animals. ra t a).

For example, the following animals may be mentioned, 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, parrots, Japanese pines, 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, perch, mullet, tuna, horse mackerel, flounder, and puffer fish.

Examples of fungi (molds) are shown below as pathogenic bacteria to which the medical/veterinary antifungal agent of the present invention can be applied. Note that 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, Aspergillus terreus; the genus Bipolaris; ; 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, Cladosporium herbarium; Coccidioides genus such as Coccidioides immitis, Coccidioides posadasii; Colletorichium tri folii etc. genus Colletotrichium such as Cryptococcus neoformans; genus Curvularia such as Curvularia lunata; genus Encephalitozoon such as Encephalitozoon cuniculi; genus Epicoccum such as Epicoccum nigrum; genus Epidermophyton such as Epidermophyton floccosum; genus Exophiala; genus Exserohilum such as Exserohilum rostratum; usarium graminarium, Fusarium solani
, Fusarium genus such as Fusarium sporotrichoides; Fonsecaea genus such as Fonsecaea monophora; Histoplasma genus such as Histoplasma capsulatum; Leptosphaeria genus such as Leptosphaeria nodorum; Malassezia genus such as Malassezia globosa; Microsporum genus such as Microsporum canis; Genus; Neurospora genus; Paecilomyces genus such as Paecilomyces lilanicus, Paecilomyces varioti; Penicillium genus such as Penicilliumchrysogenum; Phytophthora genus such as Phytophthora capsici, Phytophthora infestans; Plasmopara genus such as Plasmopara viticola; Pneumocystis genus such as Pneumocystis jirovecii; Pyricularia ory Pyricularia spp. such as zae; Pythium genus such as Pythium ultimum; Puccinia genus such as Puccinia coronata, Puccinia graminis; Rhizoctonia genus such as Rhizoctonia solani; Rhizomucor genus; Scedosporium genus such as Fusarium apiospermum, Scedosporium prolificans; Scopulariopsis genus such as Scopulariopsis brevicaulis; Sporothrix schenckii, etc. Sporothrix genus ; Talaromyces genus such as Talaromyces marneffei; Trichophyton genus such as Trichophyton mentagrophytes, Trichophyton interdigitale, Trichophyton rubrum, Trichophyton tonsurans, Trichophyton verrucosum; Trichosporon genus such as Trichosporonasahii, Trichosporon beigelii; Ustilago genus, etc.
Among these, the antifungal agent of the present invention is suitable for the genus Aspergillus, the genus Trichophyton, or the genus Candida, and is particularly suitable for the genus Aspergillus fumigatus or Trichophyton tonsurans.

Examples of fungal diseases are shown below as infectious diseases to which the medical/veterinary antifungal agent of the present invention can be applied. Note that 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. Examples of fungal infections include Aspergillus diseases such as pulmonary aspergillosis, systemic aspergillosis (which is more likely to occur in bone marrow recipients or immunosuppressed patients such as AIDS patients), and Candida (such as systemic candidiasis). Candida infection, Cryptococcus meningitis, rhinocerebral mucormycosis, pulmonary mucormycosis, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, robomycosis, Keratomycosis, sporotrichosis, chromoblastomycosis, chromomycosis, pheofifomycosis, zygomycosis, cryptococcosis, disseminated sporotrichosis, ring worm, tinea capitis, tinea corporis , tinea cruris (jock itch), tinea pedis (athlete's foot), tinea unguium (nail fungus), candidiasis of the skin, mouth, or vagina, malasseziasis, chronic mucocutaneous candidiasis, pneumocystis pneumonia, penicillium marneffei, etc. It will be done.
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. .

The medical/veterinary antifungal agent of the present invention can contain pharmaceutically acceptable additives. The additive is not particularly limited as long as it is used in known medical drugs. These are, of course, sterile and non-pyrogenic. In addition, additives can be selected as appropriate depending on 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, and examples include solid dosage forms such as tablets, powders, granules, granules, capsules, troches, and pellets; syrups; , emulsions, suspensions, solutions, drop-on agents, spot-on agents, and other liquid agents; ointments,
Mention may be made of semi-solid preparations such as gels; gaseous agents such as aerosols, vapors; nanoparticle formulations, etc.
The medical antifungal agent of the present invention can be administered by known methods. Administration methods include, for example, subcutaneous, intravenous, intramuscular, and intrasternally (injection); insertion into the anus, vagina, etc., and transdermal administration such as application, spraying, and dripping on the skin surface. Oral administration, such as taking it through the mouth; Nasal administration, such as by inhalation.

In the case of a solid preparation for oral administration, additives that can be used in the medical/veterinary antifungal agent of the present invention include solubilizing agents such as cyclodextrin or modified cyclodextrin; lactose, dextrose, sucrose, cellulose, corn starch, 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. disaggregating agents such as starch, alginic acid, sodium starch alginate or sodium glycolate; effervescing mixtures; pigments; sweeteners; wetting agents such as lecithin, polysorbates, laurylsulphates; or Examples include non-toxic and pharmacologically inert substances that are generally used in pharmaceutical preparations. 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 a liquid preparation for oral administration, additives that can be used in the medical/veterinary antifungal agent of the present invention include solubilizing agents such as cyclodextrin or modified cyclodextrin, sucrose, glycerin, mannitol, sorbitol, natural Examples include gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, and polyvinyl alcohol.

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

In the case of liquid preparations for intravenous injection, additives that can be used in the medical/veterinary antifungal agent of the present invention include carriers such as sterile water; solubilizing agents such as cyclodextrin and modified cyclodextrin; can. They can also be included in the form of sterile isotonic saline solutions.

The amount of compound (I) or its salt contained in the medical/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 depending on the administration method, the type of infected fungus, the patient's age, weight, symptoms, etc. For example, for adults, when administered orally or parenterally (injection, infusion, etc.), it can be administered once or several times a day at 0.1 to 100 mg/kg body weight.
Furthermore, the medical/veterinary antifungal agent of the present invention can be used in combination with other drugs other than pyridazinone compounds.

The present invention will be explained in more detail by showing synthesis examples below. However, the present invention is not limited in any way by the following synthesis examples.
[Example 1]
(S,E)-N-(1-(5-(5-fluoro-2-methoxyphenethyl)-3-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl) -3-Methylbutan-2-yl)isobutyramide [(S, E)-N-(1-(5-(5-fluoro-2-methoxyphenethyl)-3-(1-(isopropoxyimino)ethyl)-6-oxopyridazin -1(6H)-yl)-3-methylbutan-2-yl)isobutyramide] (Compound number: A-1)
(Step 1)
Synthesis of 6-chloro-4-((5-fluoro-2-methoxyphenyl)ethynyl)-3-methoxypyridazine

6-chloro-4-iodo-3-methoxypyridazine (0.14 g) was dissolved in N,N-dimethylformamide (4 ml) and triethylamine (6 ml). To this, 1-ethynyl-5-fluoro-2-methoxybenzene (0.085g), copper(I) iodide (0.017g), and bis(triphenylphosphine)palladium(II) dichloride (0.055g) were added. After addition, the reaction vessel was purged with nitrogen, and then stirred at 70°C for 1 hour.
A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained 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 was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.09 g (yield: 59%) of the target product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ )δ: 7.48(1H, s), 7.24 (1H, dd), 7.13-7.08 (1H, m), 6.886 (1H, dd), 4.21 (3H, s), 3.91(3H, s).
(Step 2)
1-(5-((5-fluoro-2-methoxyphenyl)ethynyl)-6-methoxypyridazin-3-yl)ethynyl )-6-methoxypyridazin-3-yl)ethan-1-one]

6-chloro-4-((5-fluoro-2-methoxyphenyl)ethynyl)-3-methoxypyridazine (0.90 g) was dissolved in 1,4-dioxane (30 ml). To this, tributyl(1-ethoxyvinyl)tin (1.44g), (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride dichloromethane adduct (0.25g), copper(I) iodide After adding lithium chloride (0.12 g) and lithium chloride (0.39 g) and purging the reaction vessel with nitrogen, the mixture was stirred under reflux conditions overnight.
The reaction solution was filtered through Celite, the filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in tetrahydrofuran (30 ml) and 3N hydrochloric acid (30 ml), followed by stirring at room temperature for 2 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained 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 was purified by amino silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.10 g (yield: 15%) of the target product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ )δ: 8.16(1H, s), 7.24 (1H, dd), 7.12-7.07 (1H, m), 6.887 (1H, dd), 4.33 (3H, s), 3.90(3H, s), 2.85 (3H, s).
(Step 3)
(E)-1-(5-(5-fluoro-2-methoxyphenethyl)-6-hydroxypyridazin-3-yl)ethan-1-one O-isopropyloxime [(E)-1-(5-(5 Synthesis of -fluoro-2-methoxyphenethyl)-6-hydroxypyridazin-3-yl)ethane-1-oneO-isopropyl oxime]

Dissolve 1-(5-((5-fluoro-2-methoxyphenyl)ethynyl)-6-methoxypyridazin-3-yl)ethan-1-one (0.18 g) in methanol (6 ml) and add palladium hydroxide. (0.018g) was added. After the reaction vessel was purged with hydrogen, it was stirred at room temperature for 3 days. The reaction solution was filtered through Celite, the filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in ethanol (3 ml) and chloroform (3 ml).
O-isopropylhydroxylamine hydrochloride (0.10 g) was added to this, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, and the resulting residue (0.13 g) was dissolved in N,N-dimethylformamide (1 ml). To this were added p-toluenesulfonic acid monohydrate (0.34 g) and lithium chloride (0.076 g), and the mixture was stirred at 70°C overnight.
Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained 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 was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.10 g (yield: 48%, 3 steps) of the target product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ )δ: 10.36(1H, s), 7.63 (1H, s), 6.89-6.83 (2H, m), 6.75-6.72 (1H, m),4.47-4.40 (1H , m),3.77 (3H, s), 2.98-2.86 (4H, m), 2.12 (3H, s), 1.29 (6H, d).
(Step 4)
tert-Butyl (S,E)-(1-(5-(5-fluoro-2-methoxyphenethyl)-3-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl )-3-Methylbutan-2-yl)carbamate [tert-butyl (S, E)-(1-(5-(5-fluoro-2-methoxyphenethyl)-3-(1-(isopropoxyimino)ethyl)-6- Synthesis of oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl)carbamate]

((E)-1-(5-(5-fluoro-2-methoxyphenethyl)-6-hydroxypyridazin-3-yl)ethan-1-one O-isopropyloxime (0.04 g) was added to N,N-dimethyl It was dissolved in formamide (0.6 ml). To this were added (S)-2-((tert-butoxycarbonyl)amino)-3-methylbutyl methanesulfonate (0.097 g) and cesium carbonate (0.19 g). , and stirred at 50°C overnight.
A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained 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 was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.03 g (yield: 49%) of the target product.
¹ H-NMR of the obtained target product is shown below.
^1H -NMR (400 MHz, CDCl ₃ )δ: 7.58(1H, s), 6.89-6.82 (2H, m), 6.76-6.73 (1H, m), 4.88 (1H, d), 4.46-4.40 (1H , m), 4.33-4.27(1H, m), 4.19-4.13 (1H, m), 4.03-3.95 (1H, m), 3.78 (3H, s), 2.92-2.84 (4H, m),2.15 (3H , s), 1.90-1.82 (1H, m), 1.30-1.24 (15H, m), 1.10 (6H, t).
(Step 5)
(S,E)-N-(1-(5-(5-fluoro-2-methoxyphenethyl)-3-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl) -3-Methylbutan-2-yl)isobutyramide [(S, E)-N-(1-(5-(5-fluoro-2-methoxyphenethyl)-3-(1-(isopropoxyimino)ethyl)-6-oxopyridazin -1(6H)-yl)-3-methylbutan-2-yl)isobutyramide] (Compound number: A-1)

tert-Butyl (S,E)-(1-(5-(5-fluoro-2-methoxyphenethyl)-3-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl )-3-methylbutan-2-yl)carbamate (0.03g) was dissolved in 1,4-dioxane (0.1ml). A 4M hydrochloric acid-dioxane solution (0.2 ml) was added to this, and the mixture was stirred at 40°C for 6 hours.
A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained 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 was dissolved in methylene chloride (1 ml). Triethylamine (0.03 ml) and isobutyryl chloride (0.01 ml) were added to this, and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.028 g (yield: 98%) of the target product. The melting point of the obtained target compound (compound number: A-1) was 151-156°C.
¹ H-NMR of the obtained target product is also shown below.
^1H -NMR (400 MHz, CDCl ₃ )δ: 7.61(1H, s), 6.89-6.83 (2H, m), 6.76-6.73 (1H, m),6.18 (1H, d), 4.62 (1H, dd ),4.48-4.38 (1H, m), 4.34-4.26 (1H, m), 3.94 (1H, dd), 3.76 (3H, s), 2.92-2.81 (4H, m),2.29-2.23 (1H, m ), 2.14 (3H, s), 1.98-1.90 (1H, m), 1.29 (6H, d), 1.06-0.99(12H, m).

Some of the pyridazinone compounds of the present invention produced in the same manner as in the above examples are shown below. The melting point (°C) is also shown as the physical property of each compound.
Compound number: A-2 (melting point 144-148°C)

Compound number: A-3 (melting point 62-65°C)

[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, Emulsion (I) containing 5% active ingredient was obtained.

The control value was calculated using the following formula.

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

(Test Example 1) Apple scab control test Water was added to emulsion (I) so that the concentration of the pyridazinone compound was 125 ppm, and the compound was dissolved to obtain a drug solution. Subsequently, the drug solution was sprayed on young apple seedlings (cultivar "Orin", 3-4 leaf stage) grown in seedling pots. After air drying, conidia of Venturia inaequalis were inoculated (treated plot). As a control, apple seedlings that were not sprayed with the drug solution were similarly inoculated (untreated group). They were left standing in a 20°C humid room with light and dark cycles repeated every 12 hours.
Two weeks after inoculation, the leaves of the apple seedlings were visually observed, the lesion area ratio was determined, and the control value was calculated.
An apple scab control test was conducted on the compounds A-1, A-2, and A-3. All compounds showed a control value of 75% or more.

(Test Example 2) Antibacterial test against Fusarium graminearum Spores of Fusarium graminearum were added and dispersed in a Minimal SD Base medium supplemented with glucose, and a pyridazinone compound dissolved in dimethyl sulfoxide was added and mixed to a concentration of 25 ppm. The mixture was dispensed onto a 96-well microplate and cultured in the dark at 25°C for 3 days. After culturing, the turbidity at a wavelength of 405 nm was measured using 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 numbers: A-1, A-2, A-3.

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 C3-6 cycloalkyloxy group Substituted 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 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- , carboxy group, group represented by R 2 -O-CO-, group represented by R 3 R 4 N-, group represented by R 3 R 4 N-CO-, R 1 -CO-O- A group represented by R 1 -CO-NR 5 -, a group represented by R 2 -O-CO-O-, 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 3 A group represented by R 4 N-SO 2 -, a group represented by R 1 O-N=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,
R2 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,
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,
R 4 each 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 be combined to form a divalent organic group,
R 5 each 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 hydrogen atom, 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, Represents a substituted or unsubstituted 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-, R N1 -CS-O-, R N1 R N1 N-CS-O-, R N1 R N2 N-, 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 - group, R N1 R N1 N-CO-CO-NR N2 -, R N1 -CS-NR N2 -, R N1 R N1 N-CS-NR N2 - group, 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 straight chain C1-6 alkyl group, a substituted or unsubstituted straight chain C2-6 alkenyl group, a substituted or unsubstituted straight chain C2-6 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, where R N1 and R N1 , or R N1 and R N2 may be taken together to form a divalent organic group;
X 4 represents a group represented by -AQ, a group represented by -B-A-Q, a group represented by -A-B-Q, or a group represented by -B-Q; ,
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 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 -, and R N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, Represents a formyl group or a substituted or unsubstituted C1-6 alkylcarbonyl group,
Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group. ]
An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.
The agricultural and horticultural fungicide according to claim 2, which is for seed treatment.
A nematocide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.
A medical/veterinary antifungal agent containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.