JP7738656B2 - Pyridazinone compounds, agricultural and horticultural fungicides, nematicides, and medical and veterinary antifungals - Google Patents

Description

The present invention relates to a pyridazinone compound and an agricultural and horticultural fungicide. More specifically, the present invention relates to a pyridazinone compound that has excellent fungicidal and antibacterial activity, is safe, and can be synthesized industrially in an advantageous manner, as well as an agricultural and horticultural fungicide containing the same as an active ingredient. It also relates to a nematicide containing the compound as an active ingredient. It also relates to an antifungal agent for medical and veterinary use that contains the compound as an active ingredient.

A variety of compounds have been proposed that have the ability to control crop diseases in agricultural and horticultural crops. For such compounds to be practically used as agricultural and horticultural fungicides, they must not only be sufficiently effective, but also unlikely to develop resistance, not cause plant damage or soil contamination, and have low toxicity to livestock and fish.

Incidentally, Patent Document 1 discloses a compound represented by formula (A) and the like, and discloses that this compound has bactericidal activity, antifungal activity, and the like.

WO2021/085389A

The objective of the present invention is to provide a pyridazinone compound that has excellent bactericidal and antibacterial activity, is highly safe, and can be synthesized industrially in an advantageous manner, as well as an agricultural and horticultural fungicide containing the compound as an active ingredient. It is also an object of the present invention to provide a nematicide containing the compound as an active ingredient. It is also an object of the present invention to provide an antifungal agent for medical and veterinary use that contains the compound as an active ingredient.

As a result of intensive research into solving the above problems, the 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 each independently represent 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, 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 C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or an unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a nitro group, a cyano group, R a group represented by ¹ -CO-, a carboxy group, a group represented by R ² -O-CO-, a group represented by R ^{3R 4N-} , a group represented by R ^{3R 4N} -CO-, a group represented by 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 ^{3R 4N} -CO-O-, a group represented by R ^3R 4N-CO-NR ⁵ -, a group represented by R ^2SO ₂ -NR ⁵ -, a group represented by R ^{3R 4N} -SO ₂ -, a group represented by R ^1O -N=CR ⁶ -, a group represented by R ^{3R 4N} -N=CR ⁶ -, or a group represented by R ¹ -N=CR ⁶ -;
R ¹ 's each independently represent 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- or 6-membered heterocyclyl group;
^R2 's each independently represent 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- or 6-membered heterocyclyl group;
^R3 's each independently represent 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- or 6-membered heterocyclyl group;
^R4 's each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein ^R3 and ^R4 may together form a divalent organic group;
^R5 's each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R ⁶ represents a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group;
^X3 is 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 alkynyl group, a group represented by R ¹ -CO-, 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, 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-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 -, R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-CO-NR ^N2 -, a group represented by R ^N1 -CS-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CS-NR ^N2 -, a group represented by R ^N1 SO ₂ -NR ^N2 - or a group represented by R ^N1 -C(═NR ^N1 )-NR ^N2 -,
R ^N1 and R ^N2 each independently represent 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, 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, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 , may together form a divalent organic group;
X ⁴ represents a group represented by Q-A-, a group represented by Q-A-B-, a group represented by Q-B-A-, a group represented by Q-SO ₂ -NR ^N3 , a group represented by Q-C(R ⁷ )=N-, a group represented by Q-NR ^N3 -SO ₂ -, a group represented by Q-N=C(R ⁷ )- or a group represented by Q-B-;
Each A independently represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or a carbonyl group;
B's each independently represent an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR ^N3 -, where R ^N3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a formyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group;
^R7 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.

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

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

In formula (II),
Y represents an oxygen atom or a sulfur atom;
X ¹ and X ² each independently represent 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, 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 C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or an unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a nitro group, a cyano group, R a group represented by ¹ -CO-, a carboxy group, a group represented by R ² -O-CO-, a group represented by R ^{3R 4N-} , a group represented by R ^{3R 4N} -CO-, a group represented by 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 ^{3R 4N} -CO-O-, a group represented by R ^3R 4N-CO-NR ⁵ -, a group represented by R ^2SO ₂ -NR ⁵ -, a group represented by R ^{3R 4N} -SO ₂ -, a group represented by R ^1O -N=CR ⁶ -, a group represented by R ^{3R 4N} -N=CR ⁶ -, or a group represented by R ¹ -N=CR ⁶ -;
R ¹ 's each independently represent 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- or 6-membered heterocyclyl group;
^R2 's each independently represent 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- or 6-membered heterocyclyl group;
^R3 's each independently represent 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- or 6-membered heterocyclyl group;
^R4 's each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein ^R3 and ^R4 may together form a divalent organic group;
^R5 's each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R ⁶ represents a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group;
^X3 is 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 alkynyl group, a group represented by R ¹ -CO-, 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, 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-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 -, R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-CO-NR ^N2 -, a group represented by R ^N1 -CS-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CS-NR ^N2 -, a group represented by R ^N1 SO ₂ -NR ^N2 - or a group represented by R ^N1 -C(═NR ^N1 )-NR ^N2 -,
R ^N1 and R ^N2 each independently represent 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, 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, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 , may together form a divalent organic group;
^X5 represents a group represented by HO-A-, a C1-6 alkoxycarbonyl group, or a halogeno group;
A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or a carbonyl group.
[8] The compound or salt thereof according to [7], wherein X ² is a group represented by R ¹ O—N═CR ⁶ —.

The pyridazinone compounds of the present invention have excellent bactericidal and antibacterial activities, are reliable in effectiveness, are highly safe, and can be synthesized industrially with advantage.
The agricultural and horticultural fungicide and nematicide of the present invention have excellent pest control effects, do not cause phytotoxicity to plants, and are less toxic to humans, livestock, and fish, and have less impact on the environment.
The antifungal agent for medical and veterinary use of the present invention has excellent antibacterial effects and is less toxic to humans, livestock, and fish.

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

In the present invention, the term "unsubstituted" means that only the core group is present. When only the name of the core group is described, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of the core group is replaced with a group having the same or different structure as the core group. Therefore, a "substituent" is another group bonded to the core group. The number of substituents may be one or more. The 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 effect of the present invention.
Specific examples of groups that can be "substituents" include the following groups.
halogeno groups such as a fluoro group, a chloro group, a bromo group, or an iodo group;
C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl groups;
C2-6 alkenyl groups such as 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, and 5-hexenyl group;
C2-6 alkynyl groups such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl, and 1,1-dimethyl-2-butynyl;

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

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

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

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

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

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

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

tri-C1-6 alkyl-substituted silyl groups such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group;
triC6-10 aryl-substituted silyl groups such as triphenylsilyl groups;
cyano group;
nitro group;

Terms such as "C1-6" indicate that the core group has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms in the 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.

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

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

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.
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 of a different structure.

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

[ ^X1 and ^X2 ]
X ¹ and X ² each independently represent 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, 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 C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or an unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a nitro group, a cyano group, R It represents a group represented by ¹ -CO-, a carboxy group, a group represented by R ² -O-CO-, a group represented by R ^{3R 4N-} , a group represented by R ^{3R 4N} -CO-, a group represented by 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 ^{3R 4N} -CO-O-, a group represented by R ^{3R 4N} -CO-NR ⁵ -, ^a group represented by R ^{2SO 2 -NR 5 -, a group represented by R 3R} _4N ^{- SO} ₂ -, a group represented by R ^1O -N=CR ⁶ -, a group represented by R ^{3R 4N} -N=CR ⁶ - or a group represented by R ¹ -N=CR ⁶ -.

Each R ¹ independently represents 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- or 6-membered heterocyclyl group.
Each ^R2 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 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.
Each ^R3 independently represents 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- or 6-membered heterocyclyl group.
Each ^R4 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Here, ^R3 and ^R4 may combine together to form a divalent organic group.
Each ^R5 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
^R6 represents a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.

Examples of the "halogeno group" in X ¹ and X ² include a fluoro group, a chloro group, a bromo group, and an iodo group.

The "C1-6 alkyl group" in ^X1 and ^X2 may be linear or branched. Examples of the "C1-6 alkyl group" in ^X1 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.

Examples of the "C2-6 alkenyl group" for ^X1 and ^X2 include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl groups.

Examples of the "C2-6 alkynyl group" for ^X1 and ^X2 include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, and a 1,1-dimethyl-2-butynyl group.

Examples of the "C1-6 alkoxy group" for ^X1 and ^X2 include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, an i-hexyloxy group, and the like.
Examples of the "C2-6 alkenyloxy group" for ^X1 and ^X2 include a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group.
Examples of the "C2-6 alkynyloxy group" for ^X1 and ^X2 include an ethynyloxy group and a propargyloxy group.

Examples of the "C1-6 alkylthio group" for ^X1 and ^X2 include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group, and the like.
Examples of the "C1-6 alkylsulfinyl group" for ^X1 and ^X2 include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.
Examples of the "C1-6 alkylsulfonyl group" in ^X1 and ^X2 include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

Substituents on ^the " ^C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkynyloxy group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group" in X1 and X2 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, n-butoxy group, s-butoxy group, i-butoxy group, t C1-6 alkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, and other C1-6 haloalkoxy groups; (C1-6 alkylideneamino)oxy groups such as (ethylideneamino)oxy group, propan-2-ylideneamino)oxy group, and other C1-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group; C6-10 aryl groups such as phenyl group, naphthyl group, and other C6-10 aryl groups; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, a C6-10 aryl group substituted by 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 4-trifluoromethylphenyl group, a 4-trifluoromethoxyphenyl group, or the like; a 5-membered heteroaryl group such as 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, or a tetrazolyl group; a 5-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or a cyano group is preferred.

Examples of the "C3-6 cycloalkyl group" for ^X1 and ^X2 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
Examples of the "C3-6 cycloalkyloxy group" for ^X1 and ^X2 include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

Examples of the "C6-10 aryl group" in ^X1 and ^X2 include a phenyl group, a naphthyl group, an indanyl group, an indenyl group, and a tetralinyl group.
Examples of the "C6-10 aryloxy group" for ^X1 and ^X2 include a phenoxy group and a naphthoxy group.

Examples of the "C6-10 arylthio group" for ^X1 and ^X2 include a phenylthio group and a naphthylthio group.
Examples of the "C6-10 arylsulfinyl group" for ^X1 and ^X2 include a phenylsulfinyl group and a naphthylsulfinyl group.
Examples of the "C6-10 arylsulfonyl group" for ^X1 and ^X2 include a phenylsulfonyl group and a naphthylsulfonyl group.

The "5- to 6-membered heterocyclyl group" for ^X1 and ^X2 is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. 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- or 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, and a dioxanyl group.
Examples of the 5- or 6-membered heteroaryl group include 5-membered heteroaryl groups such as 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; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
Examples of 5- or 6-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and an isoxazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as a dihydropyranyl group.

The "5- or 6-membered heterocyclyloxy group" for ^X1 and ^X2 has a structure in which a 5- or 6-membered heterocyclyl group and an oxy group are bonded together. Specific examples include a thiazolyloxy group and a pyridyloxy group.

Substituents on the "C3-6 cycloalkyl group", " ^C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "5- or 6 ^- membered heterocyclyl group", or "5- or 6-membered heterocyclyloxy group" in X1 and X2 include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, C1-6 alkyl groups such as butyl and n-hexyl groups; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C6-10 aryl groups such as phenyl and naphthyl groups a C6-10 aryl group substituted by 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 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; 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, a tetrahydropyridine ... Preferred are 5-membered heteroaryl groups such as a zolyl group; 5-membered heteroaryl groups 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; 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; 6-membered heteroaryl groups 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 a cyano group.
Furthermore, an oxo group is also preferred as a substituent on a "C3-6 cycloalkyl group,""C3-6 cycloalkyloxy group,""5- or 6-membered heterocyclyl group," or "5- or 6-membered heterocyclyloxy group."

In the "group represented by R ¹ -CO-" in X ¹ and X ² , R ¹ represents 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- or 6-membered heterocyclyl group.

Examples of the "C1-6 alkyl group" for ^R1 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.
Examples of the "C2-6 alkenyl group" in ^R1 include a vinyl group and a 1-propenyl group.
Examples of the "C2-6 alkynyl group" in ^R1 include an ethynyl group and a 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, chloro, bromo, and iodo groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethyl, methyl ... C1-6 haloalkoxy groups such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group; C6-10 aryl groups such as a phenyl group and a naphthyl group; C6-10 aryl groups 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, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, and a 4-trifluoromethoxyphenyl group; 5-membered heteroaryl groups such as 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; C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkoxy group, and a C1-6 haloalkoxy group. Preferred are a 5-membered heteroaryl group substituted by one or more substituents of a C1-6 alkyl group, or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, or triazinyl group; a 6-membered heteroaryl group substituted by 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 a cyano group.

Examples of the "C3-6 cycloalkyl group" in ^R1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
Examples of the "C6-10 aryl group" in ^R1 include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, and a tetralinyl group.

The "5- to 6-membered heterocyclyl group" for ^R1 is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. 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- or 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, and a dioxanyl group.
Examples of the 5- or 6-membered heteroaryl group include 5-membered heteroaryl groups such as 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; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
Examples of 5- or 6-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and an isoxazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as a dihydropyranyl group.

Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- or 6-membered heterocyclyl group" in R ¹ include halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl, and 1-fluoro-n-butyl; a C1-6 haloalkyl group such as a methyl group; a hydroxyl group; a C1-6 alkoxy group such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, or a t-butoxy group; a C1-6 haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, or a trifluoromethoxy group; a C6-10 aryl group such as a phenyl group or a naphthyl group; a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, or a 4-trifluoromethylphenyl group a C6-10 aryl 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, such as a 4-trifluoromethoxyphenyl group; a 5-membered heteroaryl group such as 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, or 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, such as a 4-trifluoromethoxyphenyl group; Preferred are: a 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or a cyano group.
Furthermore, as a substituent on a "C3-6 cycloalkyl group" or a "5- or 6-membered heterocyclyl group", an oxo group is also preferred.

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

In the "group represented by R ² -O-CO-" in X ¹ and X ² , R ² 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 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.
Specific examples of the substituent in ^R2 include the same as those exemplified for ^R1 .

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-" for X ¹ and X ² , R ³ represents 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- or 6-membered heterocyclyl group; and 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 in ^R3 or ^R4 include the same as those exemplified for ^R1 .

Here, ^R3 and ^R4 may combine together 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 a dimethylene group, a trimethylene group, and a tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group.
Preferred substituents on a "C2-5 alkylene group" or a "C1-3 alkyleneoxy-C1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl.

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

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 those in the above "group represented by R ³ R ⁴ N--".
Specific examples of the "group represented by R ³ R ⁴ N-CO-" include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, and an N-(i-propyl)-N-methylaminocarbonyl group.

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 "group represented by R ¹ -CO-".
Specific examples of the "group represented by R ¹ -CO-O-" include an acetyloxy group and an i-propylcarbonyloxy group.

In the "group represented by R ¹ -CO-NR ⁵ -" in X ¹ and X ² , R ¹ has the same meaning as in the above "group represented by R ¹ -CO-".
^R5 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 in ^R5 include the same as those exemplified for ^R1 .
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 and an ethoxycarbonyloxy group.

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

In the "group represented by R ³ R ⁴ N-CO-O-" in X ¹ and X ² , R ³ and R ⁴ have the same meanings as those in the above "group represented by R ³ R ⁴ N-".
Specific examples of the "group represented by R ³ R ⁴ N-CO-O-" include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.

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

In the "group represented by R ² SO ₂ —NR ⁵ —" for X ¹ and X ² , R ² has the same meaning as 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 —".
Specific examples of the "group represented by R ² SO ₂ -NR ⁵ -" include 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 have the same meanings as those in the above "group represented by R ³ R ⁴ N-".
Specific examples of the "group represented by R ³ R ⁴ N-SO ₂ -" include an N,N-dimethylaminosulfonyl group.

In the "group represented by R ¹ O—N═CR ⁶ —" in X ¹ and X ² , R ¹ has the same meaning as in the above "group represented by R ¹ —CO—".
^R6 represents a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.
Specific examples of the "substituted or unsubstituted C1-6 alkyl group" or "substituted or unsubstituted 5- or 6-membered heterocyclyl group" in ^R6 are the same as those exemplified for ^R1 .
Examples of the "halogeno group" in ^R6 include a fluoro group, a chloro group, a bromo group, and an iodo group.
Examples of the "mono C1-6 alkylamino group" in the "substituted or unsubstituted mono C1-6 alkylamino group" for R ⁶ include a methylamino group, an ethylamino group, an i-propylamino group, and the like.
Examples of the "di-C1-6 alkylamino group" in the "substituted or unsubstituted di-C1-6 alkylamino group" for R ⁶ include a dimethylamino group, a diethylamino group, and an N-methyl-Ni-propylamino group.
Examples of the "C1-6 alkoxy group" in the "substituted or unsubstituted C1-6 alkoxy group" for ^R6 include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, an i-hexyloxy group, etc.
Examples of the "C1-6 alkylthio group" in the "substituted or unsubstituted C1-6 alkylthio group" for ^R6 include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, and an i-propylthio group.
Examples of substituents on the "C1-6 alkoxy group,""mono-C1-6 alkylamino group,""di-C1-6 alkylamino group," or "C1-6 alkylthio group" in ^R6 include the same substituents as those exemplified as the substituents on the "C1-6 alkyl group" in ^R1 .
Specific examples of the "group represented by R ¹ O-N=CR ⁶ -" include a 1-(i-propoxyimino)ethyl group.

In the "group represented by R ³ R ⁴ N-N=CR ⁶ -" for X ¹ and X ² , R ³ and R ⁴ have the same meanings as those in the above "group represented by R ³ R ⁴ N-". R ⁶ has the same meaning as that 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 have the same meanings as those in the above "group represented by R ¹ O-N=CR ⁶ -".

In the present invention, preferred examples of X ¹ include a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Preferred examples of ^X2 include "a group represented by R ¹ O-N=CR ⁶ -".

[X ³ ]
^X3 represents 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, a group represented by R1 ^- CO-, 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 ^X3 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group.
Examples of the "straight-chain C2-6 alkenyl group" for ^X3 include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.
Examples of the "straight-chain C2-6 alkynyl group" for ^X3 include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, and a 1-hexynyl group.
Examples of the "four-membered heterocyclyl group" for ^X3 include an azetidinyl group and an oxetanyl group.
Specific examples of other substituents in ^X3 include the same as those exemplified for ^X1 and ^X2 .

In the present invention, preferred examples of ^X3 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.
In the present invention, ^X3 is more preferably a substituted linear C1-6 alkyl group.

Examples of the substituent on a linear C1-6 alkyl group, a linear C2-6 alkenyl group, a linear C2-6 alkynyl group, a C3-6 cycloalkyl group, a C6-10 aryl group, or a 4- to 6-membered heterocyclyl group include one or more substituents selected from the following group of substituents (hereinafter, this substituent may be represented by the symbol "G"):
When there are two or more substituents (G), two of them may combine to form a divalent organic group.
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, 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 C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C 3-6 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 heterocyclyl group, substituted or unsubstituted 3-10 membered heterocyclyloxy group, nitro group, cyano group, R ^a -CO- group, a carboxy group, a group represented by R ^b -O-CO-, a group represented by R ^c R ^d N-, a group represented by R ^c R ^d N-CO-, a group represented by R ^c R ^d N-NR ^d -CO-, a group represented by R ^b SO ₂ -NR ^d -CO-, a group represented by R ^a -CO-O-, a group represented by R ^a -CO-NR ^e -, a group represented by R ^a -CO-CO-NR ^e -, a group represented by R ^a -CO-NR ^e -NR ^e -, a group represented by R ^a -CO-NR ^e -NR ^e -CO-, a group represented by R ^b -O-CO-O-, a group represented by R ^b -O-CO-NR ^e -, a group represented by R ^c R ^d N-CO-O-, R ^c R ^d N-CO-NR ^e- , a group represented by R ^c R ^d N-CO-CO-NR ^e -, a group represented by R ^a -CS-NR ^e -, 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 -, a group represented by R ^h R ^j C=N-O-, a group represented by R ^a -C(=NR ^g )-NR ^e -, a group represented by 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, each R ^a independently represents 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.
Each R ^b 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 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.
Each R ^c independently represents 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- or 6-membered heterocyclyl group.
Each ^Rd 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, and ^Rc and ^Rd may combine 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.
^Rf represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
Each R ^g independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Each ^Rh independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group.
Each R ⁱ independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group, and R ^h and R ⁱ may combine to form a divalent organic group.

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

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

Examples of the "C2-6 alkenyl group" for G include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl groups.

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

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

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

Substituents on the "C1-6 alkyl group," "C2-6 alkenyl group," "C2-6 alkynyl group," "C1-6 alkoxy group," "C2-6 alkenyloxy group," "C2-6 alkynyloxy group," "C1-6 alkylthio group," "C1-6 alkylsulfinyl group," or "C1-6 alkylsulfonyl group" in G include halogeno groups such as fluoro, chloro, bromo, and iodo; hydroxyl; C1-6 alkyl groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy. C1-6 alkoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; C1-6 alkylthio groups such as methylthio and ethylthio; C1-6 alkylsulfinyl groups such as methylsulfinyl and ethylsulfinyl; C1-6 alkylsulfonyl groups such as methylsulfonyl and ethylsulfonyl; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; C6-10 aryl groups such as phenyl and naphthyl; 4-methylthio a C6-10 aryl group substituted by 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, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; 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, or a tetrazolyl group a 5-membered heteroaryl group such as; a 5-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; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl 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; or a cyano group is preferred.

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

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

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

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

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

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

Substituents on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "3-10-membered heterocyclyl group", or "3-10-membered heterocyclyloxy group" in G include halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; chloromethyl, chloroethyl, trimethylsilyl, and methyltrimethylsilyl; C1-6 haloalkyl groups such as fluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; C3-6 cycloalkyl C1-6 alkoxy groups; C6-10 aryl C1-6 alkoxy groups; (substituted with one or more substituents of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups) a substituted C6-10 aryl)C1-6 alkoxy group; a 5-membered heteroaryl C1-6 alkoxy group; a (5-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)C1-6 alkoxy group; a 6-membered heteroaryl C1-6 alkoxy group; a (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)C1-6 alkoxy group; a C1-6 alkylthio group such as a methylthio group or an ethylthio group; a methylsulfinyl group , C1-6 alkylsulfinyl groups such as ethylsulfinyl groups; C1-6 alkylsulfonyl groups such as methylsulfonyl groups and ethylsulfonyl groups; C1-6 haloalkylthio groups such as trifluoromethylthio groups and 2,2,2-trifluoroethylthio groups; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl groups and 2,2,2-trifluoroethylsulfinyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups and 2,2,2-trifluoroethylsulfonyl groups; C3-6 cycloalkyl groups such as cyclopropyl groups and cyclobutyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkylsulfinyl groups, C3-6 cycloalkyl groups substituted with one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, or a cyano group; C3-6 cycloalkenyl groups; C6-10 aryl groups such as a phenyl group or a naphthyl group; C6-10 aryl groups substituted with one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; 3- or 4-membered saturated heterocyclyl groups such as an aziridinyl group, an epoxy group, an azetidinyl group, or an oxetanyl group; a 3- or 4-membered saturated heterocyclyl group substituted by 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 5- or 6-membered saturated heterocyclyl group such as a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, or a dioxanyl group; a 5- or 6-membered saturated heterocyclyl group substituted by 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 pyrrolyl group, a furyl group, a thienyl group, an imidazoline ... 5-membered heteroaryl groups such as a zolyl 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, or a tetrazolyl group; 5-membered heteroaryl groups 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; 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; 6-membered heteroaryl groups 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 substituted 6-membered heteroaryl group; a 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, or an isoxazolinyl group; a 5-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered partially unsaturated heterocyclyl group such as a dihydropyranyl group; a 6-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a group represented by R ^G1 -CO- (wherein R ^G1 represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group; (a C6-10 aryl 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)-C1-6 alkyl group; (a 5- or 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)-C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 an alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted by one or more substituents of 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; a C6-10 aryl group; a C6-10 aryl group substituted by 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 5- or 6-membered heteroaryl group; or a 5- or 6-membered heteroaryl group substituted by 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. The same applies to R ^G1 below.);
Carboxy group;
a group represented by R ^G2 -O-CO- (wherein R ^G2 is a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group; a (C6-10 aryl 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)-C1-6 alkyl group; a (5- or 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)-C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with 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; a C6-10 aryl group; a C6-10 aryl 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 5- to 6-membered heteroaryl group; or a 5- to 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. The same applies to R ^G2 below.);
a group represented by R ^G1 R ^G1 N— (wherein R ^G1 may be the same or different, and R ^G1 may be taken together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
R ^G1 R ^G1 A group represented by N—CO— (wherein R ^G1 may be the same or different, and R ^G1 may combine with each other to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group);
a group represented by R ^G1 -CO-O-; a group represented by R ^G1 -CO-NR ^G3 - (wherein R ^G3 represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5-6-membered heteroaryl group; a (C6-10 aryl 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)-C1-6 alkyl group; or a (5-6-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); the same applies to R ^G3 below);
a group represented by R ^G2 -O-CO-O-; a group represented by R ^G2 -O-CO-NR ^G3 -; a group represented by R ^G1 R ^G1 N-CO-O- (wherein R ^G1 may be the same or different, and R ^G1 may combine with each other to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group);
a group represented by R ^G1 R ^G1 N—CO—NR ^G3 — (wherein R ^G1 may be the same or different, and R ^G1 may be taken together to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group); a group represented by R ^G2 SO ₂ —NR ^G3 —; a group represented by R ^G1 R ^G1 N—SO ₂ — (wherein R ^G1 may be the same or different, and R ^G1 may be taken together to form a trimethylene group, tetramethylene group, pentamethylene group, or 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); a group represented by (R ^G1 ) ₂ C=N-O- (wherein R ^G1 may be the same or different, and R ^G1 may combine with each other to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group);
A pentafluorosulfanyl group, a nitro group, or a cyano group is preferred.
Furthermore, an oxo group is also preferred 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."

In the "group represented by R ^a -CO-" in G, R ^a represents 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.

Examples of the "C1-6 alkyl group" for R ^a include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.
Examples of the "C2-6 alkenyl group" in R ^a include a vinyl group and a 1-propenyl group.
Examples of the "C2-6 alkynyl group" in R ^a include an ethynyl group and a 1-propynyl group.
Substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in R ^a include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; C1-6 alkylthio groups such as methylthio and ethylthio groups; C1-6 alkylsulfinyl groups such as sulfinyl group and ethylsulfinyl group; C1-6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; carboxy group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group and t-butoxycarbonyl group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; C6-10 aryl groups such as phenyl group and naphthyl group; 4- a C6-10 aryl group substituted by 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 methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; 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, a tetrazolyl group, a 5-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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; or a cyano group is preferred.

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

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

Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "3- to 10-membered heterocyclyl group" in R ^a include halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl; hydroxyl; methoxy, ethoxy, n-propoxy, i-propoxy, and n-butoxy groups. , s-butoxy group, i-butoxy group, t-butoxy group, and other C1-6 alkoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, and other C3-6 cycloalkyl C1-6 alkoxy groups; C6-10 aryl C1-6 alkoxy groups; (C6-10 aryl 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 groups; 5-membered heteroaryl C1-6 alkoxy groups; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkoxy group, a 5-membered heteroaryl substituted by one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, or a C1-6 haloalkoxy group); a 6-membered heteroaryl C1-6 alkoxy group; a (6-membered heteroaryl substituted by 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) C1-6 alkoxy group; a C1-6 alkylthio group such as a methylthio group or an ethylthio group; a C1-6 alkylsulfinyl group such as a methylsulfinyl group or an ethylsulfonyl group; a C1-6 alkylsulfonyl group such as a methylsulfonyl group or an ethylsulfonyl group; a triflate C1-6 haloalkylthio groups such as a fluoromethylthio group and a 2,2,2-trifluoroethylthio group; C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group; C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group; C3-6 cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group and a cyclopentyl group; C3-6 cycloalkyl groups substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, and a cyano group. C6-10 aryl groups such as phenyl and naphthyl groups; C6-10 aryl groups 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, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; 3- or 4-membered saturated heterocyclyl groups such as an aziridinyl group, an epoxy group, an azetidinyl group, or an oxetanyl group; C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, or a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5- or 6-membered saturated heterocyclyl group such as a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, or a dioxanyl group; a 5- or 6-membered saturated heterocyclyl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxanyl group, or a 2-membered saturated heterocyclyl group; a 5- or 6-membered saturated heterocyclyl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxanyl group, or a 2-membered saturated heterocyclyl group; 5-membered heteroaryl groups such as thiazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; 5-membered heteroaryl groups 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; 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group; 6-membered heteroaryl groups 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; a 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, or an isoxazolinyl group; a 5-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered partially unsaturated heterocyclyl group such as a dihydropyranyl group; a 6-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a group represented by R ^q1 -CO- (wherein R ^q1 is a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group; (a C6-10 aryl 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)-C1-6 alkyl group; (a 5- or 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)-C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 an alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl 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, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl 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 5- to 6-membered heteroaryl group; or a 5- to 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. 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 C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group; (a C6-10 aryl 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)-C1-6 alkyl group; (a 5- or 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)-C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 aryl an alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted by one or more substituents of 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; a C6-10 aryl group; a C6-10 aryl group substituted by 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 5- to 6-membered heteroaryl group; or a 5- to 6-membered heteroaryl group substituted by 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. The same applies to R ^q2 below.);
a group represented by R ^q1 R ^q1 N— (wherein R ^q1 may be the same or different, and R ^q1 may be joined together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
R ^q1 R ^q1 A group represented by N—CO— (wherein R ^q1 may be the same or different, and R ^q1 may combine with each other to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group);
a group represented by R ^q1 -CO-O-; a group represented by R ^q1 -CO-NR ^q3 - (wherein R ^q3 represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group; a (C6-10 aryl 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)-C1-6 alkyl group; or a (5- or 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)-C1-6 alkyl group; the same applies to R ^q3 below);
a group represented by R ^q2 -O-CO-O-; a group represented by R ^q2 -O-CO-NR ^q3 -; a group represented by R ^q1 R ^q1 N-CO-O- (wherein R ^q1 may be the same or different, and R ^q1 may combine with each other to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group);
a group represented by R ^q1 R ^q1 N—CO—NR ^q3 — (wherein R ^q1 may be the same or different, and R ^q1 may be joined together to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group); a group represented by R ^q2 SO ₂ —NR ^q3 —; a group represented by R ^q1 R ^q1 N—SO ₂ — (wherein R ^q1 may be the same or different, and R ^q1 may be joined together to form a trimethylene group, tetramethylene group, pentamethylene group, or 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); a group represented by (R ^q1 ) ₂ C=N-O- (wherein R ^q1 may be the same or different, and R ^q1 may combine with each other to 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" or a "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, and an i-propylcarbonyl group.

In the "group represented by R ^b -O-CO-" in G, R ^b 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 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.
Specific examples of the substituent in R ^b include the same as those exemplified for R ^a .

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

In the "group represented by R ^c R ^d N-" in G, R ^c represents 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- or 6-membered heterocyclyl group; and R ^d 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 in ^Rc or ^Rd include the same as those exemplified for ^Ra .
Examples of the "C1-6 alkoxy group" for ^Rd include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, an i-hexyloxy group, and the like.
Substituents on the "C1-6 alkoxy group" in R ^d include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; cyclopropyl, cyclobutyl, and cyclopentyl groups; Preferred are C3-6 cycloalkyl groups such as cyclohexyl groups; C6-10 aryl groups such as phenyl groups and naphthyl groups; C6-10 aryl groups substituted by one or more substituents selected from C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups, such as 4-methylphenyl groups, 4-methoxyphenyl groups, 4-chlorophenyl groups, 4-trifluoromethylphenyl groups, and 4-trifluoromethoxyphenyl groups; and cyano groups.

Here, R ^c and R ^d may combine together 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, a substituted or unsubstituted C1-3 alkyleneoxyC1-3 alkylene group, a substituted or unsubstituted C1-3 alkylenethioC1-3 alkylene group, and a substituted or unsubstituted C1-3 alkyleneiminoC1-3 alkylene group.
Further examples include silicon-containing divalent hydrocarbon groups such as --CH ₂ CH ₂ --Si(CH ₃ ) ₂ --CH ₂ CH ₂ --.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, and a tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group.
Examples of the "C1-3 alkylenethioC1-3 alkylene group" include a dimethylenethiodimethylene group.
Examples of the "C1-3 alkyleneiminoC1-3 alkylene group" include a dimethyleneiminodimethylene group.
Here, the imino group of the "C1-3 alkylene alkylene imino C1-3 alkylene group" means -NH-.
Preferred substituents on the "C2-5 alkylene group,""C1-3 alkyleneoxyC1-3 alkylene group,""C1-3 alkylenethioC1-3 alkylene group," and "C1-3 alkyleneiminoC1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl; methylidene; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl.

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

In the "group represented by R ^c R ^d N-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-".
Specific examples of the "group represented by R ^c R ^d N-CO-" include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, and an N-(i-propyl)-N-methylaminocarbonyl group.

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--".
Specific examples of the "group represented by R ^c R ^d N-NR ^d -CO-" include a 2,2-dimethylhydrazine-1-carbonyl group.

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

In the "group represented by R ^a -CO-O-" in G, R ^a has the same meaning as in the above "group represented by R ^a -CO-".
A specific example of the "group represented by R ^a -CO-O-" is 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 in R ^e include the same as those exemplified for R ^a .
Specific examples of the "group represented by R ^a -CO-NR ^e -" include an acetylamino group, a propionylamino group, a butyrylamino group, and an i-propylcarbonylamino group.

In the "group represented by R ^a -CO-CO-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 -".
Specific examples of the "group represented by R ^a -CO-CO-NR ^e -" include an oxopropanamide group.

In the "group represented by R ^a -CO-NR ^e -NR ^e -" 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 -".
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 "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-NR ^e -NR ^e -CO-" is 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 "group represented by R ^b -O-CO-".
Specific examples of the "group represented by R ^b -O-CO-O-" include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

In the "group represented by R ^b -O-CO-NR ^e -" 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 ^b -CO-NR ^e -".
Specific examples of the "group represented by R ^b -O-CO-NR ^e -" include a methoxycarbonylamino group.

In the "group represented by R ^c R ^d N-CO-O-" 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 those in the above "group represented by R ^c R ^d N-". ^{R e} has the same meaning as that 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 have the same meanings as those in the above "group represented by R ^c R ^d N-". R ^e has the same meaning as that 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 a 2-(methylamino)-2-oxoacetamide group and a 2-(t-butylamino)-2-oxoacetamide group.

In the "group represented by R ^a -CS-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 -".
Specific examples of the "group represented by R ^a -CS-NR ^e -" include an ethanethioamide group, a propanethioamide group, and a 2-methylpropanethioamide group.

In the "group represented by ^RcRdN - ^CS - ^NRe- " in G, ^Rc and ^Rd have the same meanings as those in the above "group represented by ^{RcRdN- "} . ^Re has the same meaning as that in the above "group represented by Ra- ^CO - ^NRe- ".
Specific examples of the "group represented by R ^c R ^d N-CS-NR ^e -" include a 3,3-dimethylthioureido group.

In the "group represented by R ^b SO ₂ -NR ^e -" 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 -".
Specific examples of the "group represented by R ^b SO ₂ --NR ^e --" include a methanesulfonylamino group.

In the "group represented by R ^c R ^d N-SO ₂ -" 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-SO ₂ -" include an N,N-dimethylaminosulfonyl group.

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

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 -".
Each R ^g independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent in R ^g include the same as those exemplified in R ^a .

In the "group represented by R ^c R ^d N-C(═NR ^g )-" in G, R ^c and R ^d have the same meanings as those in the above "group represented by R ^c R ^d N-". R ^g has the same meaning as that 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, each R ^h independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted 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 in ^Rh or R ⁱ include the same as those exemplified for R ^a .

Here, R ^h and R ⁱ may combine together 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 a dimethylene group, a trimethylene group, and a tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group.
Preferred substituents on a "C2-5 alkylene group" or a "C1-3 alkyleneoxy-C1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl.

In the "group represented by R ^h R ⁱ S═N—CO—" in G, R ^h and R ⁱ have the same meaning as those in the above "group represented by R ^h R ⁱ S(═O)═N—CO—".

In the "group represented by R ^h R ^j C═N—O—" in G, R ^h and R ^j have the same meanings as in the above "group represented by R ^h R ^j S═N—O—".
Specific examples of the "group represented by R ^h R ^j C═N—O—" include a (propan-2-ylideneamino)oxy group.

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 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 a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group.
Examples of the "oxy C1-4 alkylene group" include an oxymethylene group and an oxydimethylene group.
Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethyleneoxy group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group.
Preferred substituents on a "C1-5 alkylene group,""oxy-C1-4 alkylene group,""oxy-C2-3 alkyleneoxy group," and "C1-3 alkyleneoxy-C1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl.

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, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 3- to 10-membered heterocyclyl group, a group represented by R ^b -O-CO-, a group represented by R ^c R ^d N-, a group represented by R ^c R ^d N-CO-, a group represented by R ^a -CO-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-, and R ^c R ^d N-CO-NR ^e -, a group represented by ^RcRdN - ^CS - ^NRe- , a group represented by ^RbSO2 - _NRe- , a group represented by ^RaO - ^N =CRf-, or a group represented by ^RhRiC =N- ^{O- .}

[ ^X3 other than the above ^X3 , and R ^N1 and 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 ^{N1R N1} N-CO-O-, a group represented by R ^N1 -CS-O-, a group represented by R ^{N1R N1} N-CS-O-, a group represented by R ^{N1R N2} N-, a group represented by R ^N1 -CO-NR ^N2 -, a group represented by R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^{N1R N1} N-CO-NR ^N2 -, a group represented by R ^{N1R N1} N-CO-CO-NR ^N2 -, a group represented by R ^{N1 -} CS-NR ^N2 -, It represents a group represented by ^N1 N-CS-NR ^N2 -, a group represented by R ^N1 SO ₂ -NR ^N2 -, or a group represented by R ^N1 -C(═NR ^N1 )-NR ^N2 -.

R ^N1 and R ^N2 each independently represent 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 alkynyl group, 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, and here R ^N1 and R ^N1 , or R ^N1 and R ^N2 , may combine together to form a divalent organic group.

Examples of the "straight-chain C1-6 alkyl group" in R ^N1 and R ^N2 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group.
Examples of the "straight-chain C2-6 alkenyl group" for R ^N1 and R ^N2 include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.
Examples of the "straight-chain C2-6 alkynyl group" for R ^N1 and R ^N2 include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, and a 1-hexynyl group.
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 in R ^N1 and R ^N2 include the same as those exemplified for X ¹ .

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

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

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

In the present invention, preferred examples of A include a substituted or unsubstituted C1-6 alkylene group or a substituted or unsubstituted C2-6 alkenylene group.
Examples of the substituent on the C1-6 alkylene group or C2-6 alkenylene group include one or more substituents selected from the following group of substituents (hereinafter, this substituent may be represented by the symbol "Ga"):
When there are two or more substituents (Ga), two of them may combine to form a divalent organic group.
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, 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 mercapto group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C1-6 alkylthio ... 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- to 6-membered heterocyclyl group, substituted or unsubstituted 3- to 6-membered heterocyclyloxy group, nitro group, cyano group, R a group represented by ^a1 -CO-, a carboxy group, a group represented by 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-NR ^e1 -, a group represented by R ^b1 -O-CO-O-, a group represented by R ^b1 -O-CO-NR ^e1 -, a group represented by 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 -, a group represented by R ^a1 O-N=CR ^f1 -, R ^g1 R ^h1 A group represented by C=N-O-, an oxo group (O=), a thioxo group (S=), a divalent group represented by R ^a1 -N=, a divalent group represented by R ^a1 O-N=, a divalent group represented by R ^c1 R ^d1 N-N=, a divalent group represented by R ^a1 -CO-NR ^e1 -N=, a divalent group represented by R ^b1 -O-CO-NR ^e1 -N=, a divalent group represented by R ^b1 SO ₂ -NR ^e1 -N=.

In the above substituent group, each R ^a1 independently represents 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- or 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 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group;
R ^c1 each independently represents 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- or 6-membered heterocyclyl group;
Each R ^d1 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, and R ^c1 and R ^d1 may combine together to form a divalent organic group.
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 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 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 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 combine together to form a divalent organic group.

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

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

Examples of the "C2-6 alkenyl group" in Ga include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, and 5-hexenyl groups.

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

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

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

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

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

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

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

The "3- to 6-membered heterocyclyl group" in Ga is a group containing, as ring constituent atoms, one, two, three, or four heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms. When there are two or more heteroatoms, they may be the same or different. Examples of "3- to 6-membered heterocyclyl groups" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

Examples of the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, an azetidinyl group, an oxetanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.
Examples of the 5- or 6-membered heteroaryl group include 5-membered heteroaryl groups such as 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; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
Examples of 5- or 6-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and an isoxazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as a dihydropyranyl group.

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 groups and pyridyloxy groups.

Substituents on the "C3-6 cycloalkyl group," "C3-6 cycloalkyloxy group," "C6-10 aryl group," "C6-10 aryloxy group," "C6-10 arylthio group," "C6-10 arylsulfinyl group," "C6-10 arylsulfonyl group," "3- to 6-membered heterocyclyl group," or "3- to 6-membered heterocyclyloxy group" in Ga include halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl; Preferred are a C1-6 haloalkyl group; a hydroxyl group; a 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, or t-butoxy group; a C1-6 haloalkoxy group such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, or trifluoromethoxy group; a C6-10 aryl group such as phenyl group or naphthyl group; a C6-10 aryl group substituted by one or more substituents of any 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 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, or 4-trifluoromethoxyphenyl group; or a cyano group.

In the "group represented by R ^a1 -CO-" in Ga, R ^a1 represents 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- or 6-membered heterocyclyl group.

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

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

The "5- to 6-membered heterocyclyl group" for R ^a1 is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. 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- or 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, and a dioxanyl group.
Examples of the 5- or 6-membered heteroaryl group include 5-membered heteroaryl groups such as 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; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
Examples of 5- or 6-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and an isoxazolinyl group; and 6-membered partially unsaturated heterocyclyl groups such as a dihydropyranyl group.

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

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

In the "group represented by R ^b1 -O-CO-" in Ga, R ^b1 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 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group.
Specific examples of the substituent in R ^b1 include the same as those exemplified for R ^a1 .

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

In the "group represented by R ^c1 R ^d1 N-" in Ga, R ^c1 represents 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- or 6-membered heterocyclyl group, and R ^d1 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 in R ^c1 or R ^d1 include the same as those exemplified for R ^a1 .
Here, R ^c1 and R ^d1 may combine together 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 a dimethylene group, a trimethylene group, and a tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group.
Preferred substituents on a "C2-5 alkylene group" or a "C1-3 alkyleneoxy-C1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl.

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

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

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

In the "group represented by R ^a1 -CO-NR ^e1 -" in Ga, R ^a1 has the same meaning as in the above "group represented by R ^a1 -CO-".
R ^e1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent in R ^e1 include the same as those exemplified for R ^a1 .
A specific example of the "group represented by R ^a1 -CO-NR ^e1 -" is 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 "group represented by R ^b1 -O-CO-".
Specific examples of the "group represented by R ^b1 -O-CO-O-" include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

In the "group represented by R ^b1 -O-CO-NR ^e1 -" 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 ^b1 -CO-NR ^e1 -".
Specific examples of the "group represented by R ^b1 -O-CO-NR ^e1 -" include a methoxycarbonylamino group.

In the "group represented by R ^c1 R ^d1 N-CO-O-" 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 and an N,N-dimethylaminocarbonyloxy group.

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

In the "group represented by R ^b1 SO ₂ -NR ^e1 -" for Ga, R ^b1 has the same meaning as in the above "group represented by R ^b1 -O-CO-". ^{R e1} has the same meaning as in the above "group represented by R ^a1 -CO-NR ^e1 -".
Specific examples of the "group represented by R ^b1 SO ₂ --NR ^e1 --" include a methanesulfonylamino group.

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

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

In the "group represented by R ^g1 R ^h1 C═N—O—" in Ga, R ^g1 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 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group, and R ^h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent in R ^g1 or R ^h1 include the same as those exemplified for R ^a1 .
Here, R ^g1 and R ^h1 may combine together 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 a dimethylene group, a trimethylene group, and a tetramethylene group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group.
Preferred substituents on a "C2-5 alkylene group" or a "C1-3 alkyleneoxy-C1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl.
Specific examples of "R ^g1 R ^h1 group represented by C═N—O—" include 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=) and a methylimino group.

In the "divalent group represented by R ^a1 O-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 O-N=" include an N-hydroxyimino group and an N-methoxyimino group.

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

In the "divalent group represented by R ^a1 -CO-NR ^e1 -N=" for 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 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 -".

In the "divalent group represented by R ^b1 SO ₂ -NR ^e1 -N=" for Ga, R ^b1 has the same meaning as in the above "group represented by R ^b1 -O-CO-". ^{R e1} has the same meaning as in the above "group represented by R ^a1 -CO-NR ^e1 -".

When there are two or more substituents (Ga), 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 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 a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group.
Examples of the "oxy C1-4 alkylene group" include an oxymethylene group and an oxydimethylene group.
Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethyleneoxy group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group.
Preferred substituents on a "C1-5 alkylene group,""oxy-C1-4 alkylene group,""oxy-C2-3 alkyleneoxy group," and "C1-3 alkyleneoxy-C1-3 alkylene group" are halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, and t-butyl; or C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl.

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 C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- or 6-membered heterocyclyloxy group, a group represented by R ^a1 -CO-O-, an oxo group (O=), or a divalent group represented by R ^a1 O-N=.
In this case, a preferred example of the substituted or unsubstituted 5- or 6-membered heterocyclyloxy group is a tetrahydro-2H-pyran-4-yl group.

In the present invention, more 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 group represented by R ^a1 -CO-O-, an oxo group (O=), or a divalent group represented by R ^a1 O-N=.

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

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

Substituents on the "C1-6 alkyl group" and "C1-6 alkylcarbonyl" in R ^N3 include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; (C1-6 alkylideneamino)oxy groups such as a (ethylideneamino)oxy group and a (propan-2-ylideneamino)oxy group; C3-6 cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group; C6-10 aryl groups such as a phenyl group and a naphthyl group; C1-6 alkyl groups such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group and a 4-trifluoromethoxyphenyl group. a C6-10 aryl group substituted by one or more substituents selected from the group consisting of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 5-membered heteroaryl group such as 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; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; Preferred are a 5-membered heteroaryl group substituted by one or more substituents selected from a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group; a 6-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; or a cyano group.

[R ⁷ ]
^R7 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
The "C1-6 alkyl group" in ^R7 may be linear or branched. Examples of the "C1-6 alkyl group" in ^R7 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.
Substituents on the "C1-6 alkyl group" in ^R7 include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy groups; (ethylideneamino)oxy groups, propoxy groups, and propyl groups. (C1-6 alkylideneamino)oxy groups such as (C1-6 propan-2-ylideneamino)oxy groups; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups; C6-10 aryl groups such as phenyl and naphthyl groups; C1-6 alkyl groups and C1-6 alkoxy groups such as 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups. a C6-10 aryl group substituted by one or more substituents selected from the group consisting of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group; a 5-membered heteroaryl group such as 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, or 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; a 5-membered heteroaryl group such as 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, or a tetrazolyl group; Preferred are a 5-membered heteroaryl group substituted with one or more substituents of a 1-6 haloalkyl group or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl 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; or a cyano group.

[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 a phenyl group, a naphthyl group, an indenyl group, an indanyl group, and a tetralinyl group.

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

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

Substituents on the "C6-10 aryl group" or "5- to 10-membered heterocyclyl group" in Q include halogeno groups such as fluoro, chloro, bromo, and iodo; C1-6 alkyl groups such as methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, n-pentyl, and n-hexyl; C2-6 alkenyl groups such as vinyl; C2-6 alkynyl groups such as ethynyl; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl; C1-6 alkoxy-C1-6 alkyl groups such as methoxymethyl; hydroxyl; methoxy, ethoxy, n-propyl, and n-propyl. C1-6 alkoxy groups such as propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-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; tri C1-6 alkyl-substituted silyloxy C1-6 alkoxy groups such as trimethylsilyloxyethoxy group and t-butyldimethylsilyloxyethoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; C3-6 cycloalkyl C1-6 alkoxy groups; C6-10 aryl C1-6 alkoxy groups; (C1-6 alkyl groups, C1-6 alkoxy groups, a C6-10 aryl substituted by one or more substituents of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group)C1-6 alkoxy group; a 5-membered heteroaryl C1-6 alkoxy group; a (5-membered heteroaryl substituted by 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)C1-6 alkoxy group; a 6-membered heteroaryl C1-6 alkoxy group; a (6-membered heteroaryl substituted by 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)C1-6 alkoxy group; a methylthio group, C1-6 alkylthio groups such as a methylthio group: C1-6 alkylsulfinyl groups such as a methylsulfinyl group and an ethylsulfinyl group; C1-6 alkylsulfonyl groups such as a methylsulfonyl group and an ethylsulfonyl group; C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group: C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group; C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group; C3-6 cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group and a cyclopentyl group; C1-6 alkyl groups, C1- C3-6 cycloalkyl groups substituted with one or more substituents of any one of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, C1-6 haloalkoxy groups, or cyano groups; C3-6 cycloalkenyl groups such as cyclopropenyl groups, cyclobutenyl groups, and cyclopentenyl groups; C6-10 aryl groups such as phenyl groups and naphthyl groups; C6-10 aryl groups substituted with one or more substituents of any one of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups, such as 4-methylphenyl groups, 4-methoxyphenyl groups, 4-chlorophenyl groups, 4-fluorophenyl groups, 4-trifluoromethylphenyl groups, and 4-trifluoromethoxyphenyl groups; azido saturated heterocyclyl groups having 3 to 4 members such as lysinyl, epoxy, azetidinyl, and oxetanyl; saturated heterocyclyl groups having 3 to 4 members substituted with one or more substituents selected from C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, and C1-6 haloalkoxy; saturated heterocyclyl groups having 5 to 6 members such as pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl, and dioxanyl; saturated heterocyclyl groups having 5 to 6 members substituted with one or more substituents selected from C1-6 alkyl, C1-6 alkoxy, halogeno, C1-6 haloalkyl, and C1-6 haloalkoxy; saturated heterocyclyl groups having a ring structure; 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl; 5-membered heteroaryl groups substituted with one or more substituents selected from C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups. a 6-membered heteroaryl group substituted by one or more substituents of any one of a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, an isoxazolinyl group, etc.; a 5-membered partially saturated heterocyclyl group substituted by one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered partially unsaturated heterocyclyl group such as a dihydropyranyl group; a 6-membered partially saturated heterocyclyl group substituted by one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a group represented by R ^Q1 -CO- (wherein R ^Q1 is a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group; (a C6-10 aryl 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)-C1-6 alkyl group; (a 5- or 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)-C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 an alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted by one or more substituents of 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; a C6-10 aryl group; a C6-10 aryl group substituted by 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 5- to 6-membered heteroaryl group; or a 5- to 6-membered heteroaryl group substituted by 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. 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 C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group; a (C6-10 aryl 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) C1-6 alkyl group; a (5- or 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) C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with 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; a C6-10 aryl group; a C6-10 aryl 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 5- to 6-membered heteroaryl group; or a 5- to 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. The same applies to R ^Q2 below.);
a group represented by R ^Q1 R ^Q1 N- (wherein R ^Q1 may be the same or different, and R ^Q1 may be joined together to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group);
R ^Q1 R ^Q1 A group represented by N—CO— (wherein R ^Q1 may be the same or different, and ^{R Q1} may be joined together to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group);
a group represented by R ^Q1 -CO-O-; a group represented by R ^Q1 -CO-NR ^Q3 - (wherein R ^Q3 represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted with one or more substituents of a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5-6-membered heteroaryl group; a (C6-10 aryl 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)-C1-6 alkyl group; or a (5-6-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)-C1-6 alkyl group; the same applies to R ^Q3 below);
a group represented by R ^Q2 -O-CO-O-; a group represented by R ^Q2 -O-CO-NR ^Q3 -; a group represented by R ^Q1 R ^Q1 N-CO-O- (wherein R ^Q1 may be the same or different, and R ^Q1 may combine with each other to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group);
a group represented by R ^Q1 R ^Q1 N—CO—NR ^Q3 — (wherein R ^Q1 may be the same or different, and R ^Q1 may be joined together to form a trimethylene group, tetramethylene group, pentamethylene group, or dimethyleneoxydimethylene group); a group represented by R ^Q2 SO ₂ —NR ^Q3 —; a group represented by R ^Q1 R ^Q1 N—SO ₂ — (wherein R ^Q1 may be the same or different, and R ^Q1 may be joined together to form a trimethylene group, tetramethylene group, pentamethylene group, or 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); a group represented by (R ^Q1 ) ₂ C=N-O- (wherein R ^Q1 may be the same or different, and R ^Q1 may combine with each other to 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 an agriculturally and horticulturally acceptable salt. Examples thereof include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine; and ammonium salts.

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

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

In formula (II),
Y represents an oxygen atom or a sulfur atom;
X ¹ and X ² each independently represent 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, 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 C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or an unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a nitro group, a cyano group, R a group represented by ¹ -CO-, a carboxy group, a group represented by R ² -O-CO-, a group represented by R ^{3R 4N-} , a group represented by R ^{3R 4N} -CO-, a group represented by 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 ^{3R 4N} -CO-O-, a group represented by R ^3R 4N-CO-NR ⁵ -, a group represented by R ^2SO ₂ -NR ⁵ -, a group represented by R ^{3R 4N} -SO ₂ -, a group represented by R ^1O -N=CR ⁶ -, a group represented by R ^{3R 4N} -N=CR ⁶ -, or a group represented by R ¹ -N=CR ⁶ -;
R ¹ 's each independently represent 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- or 6-membered heterocyclyl group;
^R2 's each independently represent 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- or 6-membered heterocyclyl group;
^R3 's each independently represent 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- or 6-membered heterocyclyl group;
^R4 's each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein ^R3 and ^R4 may together form a divalent organic group;
^R5 's each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R ⁶ represents a halogeno group, an amino group, a substituted or unsubstituted mono-C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group;
^X3 is 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 alkynyl group, a group represented by R ¹ -CO-, 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, 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-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 -, R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-CO-NR ^N2 -, a group represented by R ^N1 -CS-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CS-NR ^N2 -, a group represented by R ^N1 SO ₂ -NR ^N2 - or a group represented by R ^N1 -C(═NR ^N1 )-NR ^N2 -,
R ^N1 and R ^N2 each independently represent 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, 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, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 , may together form a divalent organic group;
^X5 represents a group represented by HO-A-, a C1-6 alkoxycarbonyl group, or a halogeno group;
A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or a carbonyl group.

In formula (II), each symbol has the same meaning as in formula (I).
Examples of the "C1-6 alkoxycarbonyl group" for ^X5 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 of the "halogeno group" in ^X5 include a fluoro group, a chloro group, a bromo group, and an iodo group.
The compound of formula (II) is preferably a compound in which X ² is a group represented by R ¹ O—N═CR ⁶ — or a salt thereof.

[Salts of Production Intermediates and Production Methods]
Examples of salts of the intermediate compound represented by formula (II) include the same salts as those of the compound represented by formula (I).
The method for producing the intermediate represented by formula (II) is not limited. For example, it can be obtained by known methods such as those described in the Examples. Furthermore, the salt of the intermediate can be obtained from compound (II) by known methods.

[Agricultural and horticultural fungicides]
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 fungicidal effect.

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

Examples of plant diseases (pathogens) that can be controlled are shown below.
Sugar beet: Cercospora beticola, Aphanomyces cochlioides, Root rot (Thanatephorus cucumeris), Leaf rot (Thananatephorus cucumeris), Rust (Uromyces betae), Powdery mildew (Oidium sp.), Spot disease (Ramularia beticola), Seedling damping off (Aphanomyces cochlioides, Pythium Groundnut: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum, Alternaria alternata, Sclerotium rolfsii, Mycosphaerella berkeleyi, Calonectria ilicicola) etc. Cucumber: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine splitting (Fusarium oxysporum), sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassiicola), seedling damping-off (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), bacterial spot (Pseudomonas syringae pv. Lachrymans), etc. Tomato: Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), Verticillium wilt (Verticillium albo-atrum, Verticillium dahliae), Powdery mildew (Oidium neolycopersici), Ring blight (Alternaria solani), Leaf mold (Pseudocercospora fuligena), Bacterial wilt (Ralstonia solanacearum), Sclerotinia sclerotiorum, etc. Eggplant: Gray mold (Botrytis cinerea), Black blight (Corynespora melongenae), Powdery mildew (Erysiphe cichoracearum), Leaf mold (Mycovellosiella nattrassii), Sclerotinia sclerotiorum, Verticillium wilt (Verticillium dahliae), Brown spot (Phomopsis vexans), etc. Pepper: Late blight (Phytophthora capsici), Gray mold (Botrytis cinerea), Sclerotinia sclerotiorum, Anthracnose (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), Powdery mildew (Leveillula taurica), etc. Strawberry: Gray mold (Botrytis cinerea), Powdery mildew (Sphaerotheca humuli), Anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), Late blight (Phytophthora cactorum), Soft rot (Rhizopus stolonifer), Yellows (Fusarium oxysporum), Wilt (Verticillium dahliae), Sclerotinia sclerotiorum, etc. Onion: Gray rot (Botrytis allii), Gray mold (Botrytis cinerea), Botrytis squamosa, Peronospora destructor, Phytophthora porri, Ciborinia allii, Botrytis squamosa, Fusarium oxysporum, Pyrenochaeta terrestris, 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), Sclerotium rolfsii), pink root rot (Pyrenochaeta terrestris), etc. Cabbage: Clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campestris pv. campestris), bacterial black spot (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), downy mildew (Peronospora parasitica), sclerotinia sclerotiorum, sooty mildew (Alternaria brassicicola), gray mold (Botrytis cinerea), root rot (Phoma lingam), Pythium rot (Pythium aphanidermatum, Pythium ultimum), white rust (Albugo macrospora), etc. Lettuce: Rot (Pseudomonas cichorii, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremia lactucae), gray mold (Botrytis cinerea), sclerotinia sclerotiorum, big-vein disease (Mirafiori lettuce big-vein ophiovirus), root rot (Fusarium oxysporum), bottom rot (Rhizoctonia solani), powdery mildew (Golovinomyces orontii), etc. Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular spot (Phaeoisariopsis griseola), etc. Peas: Brown spot (Mycosphaerella blight), gray mold (Botrytis cinerea), sclerotinia sclerotiorum), powdery mildew (Erysiphe pisi), etc.

Apple: Powdery mildew (Podosphaera leucotricha), black spot (Venturia inaequalis), monilinia (Monilinia mali), black spot (Mycosphaerella pomi), canker (Valsa mali), leaf spot (Alternaria mali), red spot (Gymnosporangium yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), sooty spot (Zygophiala jamaicensis), sooty spot (Gloeodes pomigena), purple root rot (Helicobasidium mompa), white root rot (Rosellinia necatrix), gray mold (Botrytis cinerea), fire blight (Erwinia amylovora), silver leaf (Chondrostereum) Plum: Black spot (Cladosporium carpophilum), Gray mold (Botrytis cinerea), Brown rot (Monilinia mumecola), Sooty spot (Peltaster sp.), Fruit blister (Taphrina pruni), Brown hole (Phloeosporella padi), Persimmon: Powdery mildew (Phyllactinia kakicola), Anthracnose (Gloeosporium kaki), Angular leaf spot (Cercospora kaki), Round leaf spot (Mycosphaerella nawae), Gray mold (Botrytis cinerea), Sooty spot (Zygophiala jamaicensis), Peach: Brown rot (Monilinia fructicola, Monilinia fructigena), Cladosporium carpophilum, Phomopsis sp., Xanthomonas campestris pv. pruni, Taphrina deformans, Colletotrichum gloeosporioides, Phloeosporella padi, Coriolus versicolor, etc. Almond: Monilinia laxa, Stigmina carpophila, Cladosporium carpophilum, Polystigma rubrum, Alternaria alternata, Colletotrichum gloeospoides, etc. Hawt: Monilinia fructicola, Colletotrichum acutatum), black spot (Alternaria sp.), young fruit sclerotinia (Monilinia kusanoi), brown hole (Mycosphaerella cerasella), powdery mildew (Podosphaera tridactyla), etc. Grapes: gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), white cotton snow disease (pathogen unidentified), crown gall (Rhizobium radiobacter, Rhizobium vitis), etc. Pears: black spot (Venturia nashicola), red spot (Gymnosporangium asiaticum), black spot (Alternaria kikuchiana), ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), canker (Phomopsis fukushii), brown spot (Stempphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: ring spot (Pestalotiopsis longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blight (Exobasidium reticulatum), red burn (Pseudomonas syringae), blight (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcettii), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), canker (Xanthomonas campestris pv. Citri), powdery mildew (Oidium sp.), late blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc. Kiwifruit: blossom rot bacterial disease (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytis cinerea), fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), sooty spot (Pseudocercospora actinidiae), etc. Olives: anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), peacock spot (Spilocaea oleaginea), etc. Chestnut: Anthracnose (Colletotrichum gloeosporioides), etc.

Wheat: Powdery mildew (Blumeria graminis f.sp. tritici), Fusarium head blight (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), Fusarium rust (Puccinia recondita), Yellow rust (Puccinia striiformis), Brown snow rot (Pythium iwayamai), Monographella nivalis, Pseudocercosporella herpotrichoides, Septoria tritici, Leptosphaeria nodorum, Typhula incarnata, Myriosclerotinia borealis, Gaeumannomyces graminis), ergot disease (Claviceps purpurea), smut (Tilletia Barley: Spotted leaf disease (Pyrenophora graminea), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia) spp.) etc. Rice: Pyricularia spp. oryzae), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), hemp leaf blight (Cochliobolus miyabeanus), seedling damping-off (Pythium graminicola), white leaf blight (Xanthomonas oryzae), bacterial seedling blight (Burkholderia plantarii), brown stripe (Acidovorax avenae), bacterial grain rot (Burkholderia glumae), leaf streak (Cercospora oryzae), rice smut (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), black-bellied rice (Alternaria padwickii), pink rice (Epicoccum purpurascens), etc. Tobacco: sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum), late blight (Phytophthora nicotianae), etc. Tulips: Gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf rot (Rhizoctonia solani), bulb rot (Fusarium oxysporum), skin rot (Rhizoctonia solani), etc. Roses: Black spot (Diplocarpon rosae), powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Chrysanthemums: Gray mold (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 wilt (Fusarium solani), etc. Gerbera: Gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanthii), etc. Lily: Leaf blight (Botrytis elliptica, Pestalotiopsis sp.), Gray mold (Botrytis cinerea), etc. Sunflower: Downy mildew (Plasmopara halstedii), Sclerotinia sclerotiorum, Gray mold (Botrytis cinerea), etc. Bentgrass: Snow mold (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: Purple spot (Cercospora kikuchii), downy mildew (Peronospora manshurica), stem rot (Phytophthora sojae), rust (Phakopsora pachyrhizi), sclerotinia sclerotiorum, anthracnose (Colletotrichum truncatum), gray mold (Botrytis cinerea), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Potato: Late blight (Phytophthora infestans), summer blight (Alternaria solani), black spot (Thanatephorus cucumeris), half-leaf wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), black leg (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia sclerotiorum, etc. Dioscorea: leaf blight (Cylindrosporium dioscoreae), anthracnose (Colletotrichum gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Sweet potato: purple root rot (Helicobasidium mompa), fusarium wilt (Fusarium oxysporum), etc. Taro: late blight (Phytophthora colocasiae), stem rot (Rhizoctonia solani), etc. Ginger: rhizome rot (Pythium ultimum, Pythium myriotylum), white spot (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: anthracnose (Colletotrichum aenigma), canker (Xanthomonas campestris), stem rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), gray mold (Botrytis cinerea), etc. Rapeseed: sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae), powdery mildew (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), downy mildew (Peronospora parasitica), etc. Coffee: rust (Hemileia vastatrix), anthracnose (Colletotrichum coffeanum), brown eye (Cercospora coffeicola), etc. Sugarcane: brown rust (Puccinia melanocephala), etc. Maize: hailstone (Gloeocercospora sorghi), rust (Puccinia sorghi), southern rust (Puccinia polysora), ear smut (Ustilago maydis), southern leaf blight (Cochliobolus heterostrophus), sooty leaf blight (Setosphaeria turcica), damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: Seedling damping-off (Pythium sp.), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hops: Downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.

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

Specific examples of various plant-parasitic nematodes that can be controlled by the nematicide of the present invention are listed below: (1) Tylenchida
(a) Anguinidae, for example, Anguina funesta, Anguina tritici, from the genus Anguina; Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus, from the genus Ditylenchus;
(b) Aphelenchoididae, for example, Aphelenchoides spp., such as rice root nematode (Aphelenchoides besseyi), strawberry nematode (Aphelenchoides fragariae), and peel nematode (Aphelenchoides ritzemabosi); Bursaphelenchus spp., such as pine wood nematode (Bursaphelenchus xylophilus);
(c) from the family Belonolaimidae, for example, from the genus Belonolaimus, Belonolaimus longicaudatus; from the genus Tylenchorhynchus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius;
(d) of the Criconematidae, e.g., Criconema mutabile;
(e) Dolichodoridae, for example, Dolichodorus mediterraneus;
(f) Ecphyadophoridae, e.g., Ecphyadophora tenuissima
(g) from the family Hemicycliophoridae, for example, Loofia thienemanni;
(h) Heteroderidae, for example, Globodera spp., potato cyst nematode (Globodera rostochiensis), potato white cyst nematode (Globodera pallida), tobacco cyst nematode (Globodera tabacum); Heterodera spp., wheat cyst nematode (Heterodera avenae), Heterodea cruciferae, soybean cyst nematode (Heterodera glycines), sugar beet cyst nematode (Heterodera schachtii), clover cyst nematode (Heterodera trifolii);
(i) from the family Hoplolaimidae, for example, from the genus Helicotylenchus, Helicotylenchus dihystera, Helicotylenchus multicinctus; from the genus Hoplolaimus, Hoplolaimus columbus, Hoplolaimus galeatus; and others, such as Rotylenchus robustus, Rotylenchulus reniformis;
(j) Meloidogynidae, for example, Meloidogynes pp., Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and Meloidogyne thamesi;
(k) Nothotylenchidae, for example, the strawberry nematode (Nothotylenchus acris);
(l) Paratylenchidae, for example, Paratylenchus spp., such as Paratylenchus curvitatus and Paratylenchus elachistus;
(m) Pratylenchidae, for example, Pratylenchus spp. species, such as Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus, Pratylenchus fallax, Pratylenchus goodeyi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus scribneri, Pratylenchus vulnus, Pratylenchus zeae); others include the false root-knot nematode (Nacobbus aberrans), the banana root-miner nematode (Radopholus similis), the citrus root nematode (Tylenchulus semipenetrans), and the citrus root-miner nematode (Radopholus citrophilus).

(2) Dorylaimida
(a) From the family Longidoridae, for example, from the genus Longidorus, Longidorus elongates; from the genus Xiphinema, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Xiphinema diversicaudatum.

(3) Triplonchida
(a) Family Trichodoridae, e.g., Trichodorus primitivus, Paratrichodorus minor.

[Application method/mixture]
The agricultural and horticultural fungicide or nematicide of the present invention is preferably used on plants such as grains, vegetables, root vegetables, potatoes, fruit trees, trees such as tea, coffee and cacao, pasture grasses, turf grasses, and cotton.

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, tuberous roots, shoots, and cuttings. Nematicides can be applied to roots, tubers, tuberous roots, and the like. They can also be applied to improved varieties and cultivars of these plants, as well as mutants, hybrids, and genetically modified organisms (GMOs).

The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage application, soil application, and water surface application to control various diseases that occur in agricultural and horticultural crops, including flowers, turf, and pasture grass. Nematicides can be used for seed treatment and soil application.

The agricultural and horticultural fungicide or nematicide of the present invention may contain components other than the pyridazinone compound of the present invention. Examples of other components include known carriers used for formulation. Examples of other components include conventionally known fungicides, insecticides/miticides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feed, etc. The inclusion of such other components may produce a synergistic effect.
That is, one embodiment of the present invention is an agricultural and horticultural fungicide containing one or more additional fungicides.

Preferred examples of fungicides that can be mixed or used in combination with the agricultural and horticultural fungicide or nematicide of the present invention include compounds listed on the Fungicide Resistance Action Committee (FRAC) website (https://www.frac.info/), and agriculturally acceptable salts or derivatives thereof.
Specific examples include compounds selected from the following group:

Fungicide:

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

(B) Agents acting on cytoskeleton and motor proteins:
B1) to B3) β-tubulin polymerization inhibitors: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, ethaboxam, chlorfenazole, debacarb, trichlamide, and zarilamid.
B4) Pencycuron, an inhibitor of cell division (unknown site of action).
B5) Spectrin-like protein delocalization inhibitors: fluopicolide and fluopimomide.
B6) Actin/myosin/fimbrin function inhibitors: phenamacril, metrafenone, pyriofenone.

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

(D) Agents acting on amino acid and protein synthesis:
D1) Methionine biosynthesis (cgs gene) inhibitors: cyprodinil, mepanipyrim, pyrimethanil.
D2) Blasticidin S, an inhibitor of protein synthesis (ribosome translation termination step).
D3), D4) Protein synthesis (ribosome translation initiation step) inhibitors: kasugamycin, kasugamycin hydrochloride, streptomycin.
D5) Oxytetracycline, an inhibitor of protein synthesis (ribosomal polypeptide elongation step).

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

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

(G) Cell membrane sterol biosynthesis inhibitors G1) C14 demethylase (erg11/cyp51) inhibitors of sterol biosynthesis: triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole mizole, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole Flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, mefentrifluconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, fluoxytioconazole, fluconazole, furconazole, fluconazole-cis, and diniconazole-M.
G2) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine, and buthiobate.
G3) Fenhexamid and fenpyrazamine, inhibitors of 3-ketoreductase (erg27) in the C4 demethylation of sterol biosynthesis.
G4) Squalene epoxidase (erg1) inhibitors of the sterol biosynthesis pathway: pyributicarb, naftifine, and terbinafine.

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

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

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

(U) Agents with unknown mechanism of action:
Cymoxanil, teclofthalam, triazoxide, flusulfamide, diclomezine, cyflufenamid, dodine, dodine free base, flutianil, ferimzone, tebufloquin, picarbutrazox, validamycin, bethoxazin, cyprofuram, flumetover, nitrothal-isopropyl, propamidine, ipflufenoquin, pyridaclomethicone Pyridachlometyl, Pyrapropoyne, Aminopyrifen, Ipfentrifluconazole, Quinofumelin, Dipymetitrone, Chlorinconazide, Seboctylamine, Flumetylsulforim, Flufenoxadiazam.

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

(BM) Biopesticides/Biological Pesticides with Multiple Mechanisms of Action:
a) Plant extracts Polypeptide (lectin), phenolic compounds, sesquiterpenes, triterpenoids, coumarins, terpene hydrocarbons, terpene alcohols, terpene phenols, extract from the cotyledons of lupine plantlets, extract from Swinglea glutinosa, extract from Melaleuca alternifolia (tea tree oil), plant oils (mixtures), eugenol, geraniol, thymol, α-pinene, α Alpha-terpinene, α-terpineol, α-terpinolene, gamma-terpinene, d-limonene, orange oil, linalool, menthol, ursolic acid, oleanolic acid, neem oil.
b) Microorganisms (microbial strains or their extracts or metabolites)
Trichoderma atroviride strain I-1237, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1, Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain 77B;
Trichoderma asperellum strain T34, Trichoderma asperellum strain kd;
Trichoderma harzianum strain T-22;
Trichoderma spp., such as Trichoderma virens strain G-41.
Gliocladium spp., such as Gliocladium catenulatum strain J1446.
Clonostachys spp., such as Clonostachys rosea strain CR-7.
Coniothyrium spp., such as Coniothyrium minitans strain CON/M/91-08.
Talaromyces spp., such as Talaromyces flavus strain SAY-Y-94-01.
Saccharomyces spp., such as Saccharomyces cerevisae strain LAS02.
Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332;
Bacillus spp. such as Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis strain HAI-0404; and Bacillus spp. such as Bacillus simplex.
Paenibacillus spp.
Burkholderia spp.
Fusarium spp.
Pseudomonas spp. such as Pseudomonas chlororaphis strain AFS009, Pseudomonas fluorescens, and Pseudomonas rhodesiae HAI-0804.
Streptomyces spp. such as Streptomyces griseovirides strain K61 and Streptomyces lydicus strain WYEC108.
Agrobacterium spp., such as Agrobacterium radiobacter.
Erwinia spp., including non-pathogenic Erwinia carotovora (Erwinia carotovora subsp. carotovora).
Variovorax spp., such as Variovorax paradoxus.
Lactobacillus spp., such as Lactobacillus plantarum.
c) Other agents: Substances that can act as elicitors, such as yeast or its extract, β-glucan, chitin or chitosan or fragments thereof, β-aminobutyric acid, 2,6-dichloroisonicotinic acid, salicylic acid or its derivatives, algae extract, algae extract (hydrolyzate), jasmine flower extract, sodium alginate, oligosaccharides, trehalose, polysaccharides, lipids, lipopolysaccharides, fatty acids, glycolipids, glycoproteins, glycopeptides, proteins or peptides derived from plants and/or pathogenic microorganisms, and ergosterol.

(N) Unclassified agents: mineral oils, organic oils, inorganic salts, materials of biological origin, potassium bicarbonate, sodium hydrogen carbonate, calcium carbonate, calcium hydroxide, potassium iodide, potassium phosphonates, chitosan hydrochloride, urea.

Preferred examples of insecticides and acaricides that can be mixed or used in combination with the agricultural and horticultural fungicide or nematicide of the present invention include compounds listed on the website of the IRAC (Insecticide Resistance Action Committee) (https://irac-online.org/), and agriculturally acceptable salts or derivatives thereof.
Specific examples include compounds selected from the following group:

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

(1B) Acetylcholinesterase (AChE) inhibitors (organophosphorus):
Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos DDVP), Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylate salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, bromophos-ethyl, cyanofenphos, demeton-S-methylsulfone ), Dialifos, Dichlofenthion, Dioxabenzofos, Etrimfos, Fensulfothion, Fonofos, Formothion, Iodofenphos, Isazofos, Isocarbofos, Methacrifos, Phosphocarb, Pirimiphos-ethyl, Propaphos, Prothoate, Sulprofos.

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

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

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators:
Spinetoram, Spinosad.

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

(7) Juvenile hormone mimics:
Hydroprene, Kinoprene, Methoprene, Fenoxycarb, Pyriproxifen, Diofenolan, Epophenonane, Triprene.

(8) Other non-specific (multi-site) inhibitors:
Alkyl halides such as methyl bromide, chloropicrin, sodium aluminum fluoride, sulfuryl fluoride, borax, boric acid, disodium octaborate, sodium borate, sodium metaborate, tartar emetic, dazomet, metam, metam sodium, metam potassium.

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

(10) Mite growth inhibitor:
Clofentezine, diflovidazin, hexythiazox, etoxazole.

(11) Microbial-derived insect midgut membrane disrupting agent:
Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis, Bt crop proteins, Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1, Bacillus sphaericus.
Note: "Bt" stands for Bacillus thuringiensis, and "proteins contained in Bt crops" refer to proteins produced within crops that have incorporated the genes for the toxin proteins (Cry1Ab, etc.) produced by Bt (Bacillus thuringiensis).

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

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

(14) Nicotinic acetylcholine receptor (nAChR) channel blocker:
Bensultap, Cartap hydrochloride, Thiosultap, Thiosultap-sodium.

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

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

(17) Molting inhibitor:
Cyromazine.

(18) Ecdysone receptor agonist:
Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.

(19) Octopamine receptor agonists:
Amitraz, Chlordimeform.

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

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

(22) Voltage-dependent sodium channel blockers:
Indoxacarb, Metaflumizone.

(23) Acetyl-CoA carboxylase inhibitor:
Spirodiclofen, Spiromesifen, Spirotetramat, Spiropidione.

(24) Mitochondrial electron transport chain complex IV inhibitor:
Aluminum phosphide (Al-phosphide), calcium phosphide (Ca-phosphide), zinc phosphide (Zn-phosphide), phosphine, calcium cyanide (Ca-cyanide), sodium cyanide (Na-cyanide), potassium cyanide (K-cyanide).

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

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

(27) Chord-tone organ modulator Target site unspecified:
Flonicamid.

(28) GABA-gated chloride ion (chloride ion) channel allosteric modulator:
Broflanilide, Fluxametamide, Isocycloseram, Afoxolaner, Fluralaner, Lotilaner, Sarolaner.

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

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

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

Furthermore, an antiparasitic agent can also be mixed in. Specific examples of the antiparasitic agent that can be mixed in include compounds selected from the following group:
Anthelmintics:
(a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimin, thiophanate; thiabendazole, cambindazole;
(b) Salicylanilides: closantel, oxyclozanide, rafoxanide, niclosamide;
(c) Substituted phenols: nitroxynil, nitrosquanate;
(d) Pyrimidines: pyrantel, morantel;
(e) Imidazothiazoles: levamisole, tetramisole;
(f) Tetrahydropyrimidines: praziquantel, epsiprantel;
(g) Other anthelmintics: cyclodiene, ryania, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel; thiacetarsamide, melarsomine, arsenamide.

[Formulation]
In addition to the pyridazinone compound of the present invention, the agricultural and horticultural fungicide or nematicide of the present invention can contain other active ingredients and agriculturally and horticulturally acceptable auxiliary ingredients for formulation (e.g., inorganic carriers, organic carriers, surfactants, solvents, etc.).
The agricultural and horticultural fungicide or nematicide of the present invention is not particularly limited by its formulation. For example, it can be in the form of a wettable powder, emulsifiable concentrate, dust, granule, water-soluble powder, suspension, water-dispersible granule, tablet, etc. The method for preparing the formulation is not particularly limited, and a known preparation method can be used depending on the formulation.
Some formulation examples are shown below. Note that the formulations shown below are merely examples and can be modified within the scope of the present invention, and the present invention is not limited by the following formulation examples. Unless otherwise specified, "parts" means "parts by weight."

(Formulation Example 1: Wettable powder)
40 parts of the pyridazinone compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder containing 40% of the active ingredient.
(Formulation Example 2: Emulsion)
30 parts of the pyridazinone compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsifiable concentrate containing 30% of the active ingredient.
(Formulation Example 3: Granules)
Five parts of the pyridazinone compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then granulated to particle diameters 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, and the mixture was thoroughly kneaded with water, granulated, and dried to obtain granules containing 5% of the active ingredient.
(Formulation Example 5: Suspension)
10 parts of the pyridazinone compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of a sodium salt of polycarboxylic acid, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized until the particle size becomes 3 microns or less, to obtain a suspension containing 10% of the active ingredient.
(Formulation Example 6: Water Dispersible Granule)
40 parts of the pyridazinone compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzenesulfonate, 8 parts of sodium ligninsulfonate, and 5 parts of a formaldehyde condensate of sodium alkylbenzenesulfonate are uniformly mixed and finely ground, and then an appropriate amount of water is added and the mixture is kneaded to form a clay-like substance. The clay-like substance is granulated and then dried to obtain a water dispersible granule containing 40% of the active ingredient.

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

In this specification, "animal" refers to vertebrates such as pets, livestock, poultry, animals kept in zoos and aquariums, captive wild animals, and research and experimental animals.

For example, the following animals may be mentioned, but the specific examples of animals are not limited to these.
Mammals such as sheep, goats, pigs, horses, cows, water buffalo, donkeys, mules, camels, llamas, alpacas, wild boars, reindeer, deer, mink, elephants, bears, kangaroos, foxes, dogs, cats, squirrels, rabbits, mice, rats, guinea pigs, hamsters, monkeys, and ferrets.
Birds such as pigeons, parakeets, parrots, Java sparrows, Bengalese finches, canaries, chickens, ducks, turkeys, wild ducks, pheasants, peacocks, ostriches, swans, sparrows, quails, 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, sea bream, amberjack, salmon, mackerel, sea bass, grouper, tuna, horse mackerel, flounder, and pufferfish.

Examples of fungi (molds) as pathogenic bacteria to which the medical and veterinary antifungal agent of the present invention can be applied are shown below, but the specific examples are not limited to these.
For example, the genus Absidia, such as Absidia corymbifera; the genus Acremonium; the genus Alternaria, such as Alternaria alternata; the genus Aspergillus, such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, Aspergillus parasiticus, and Aspergillus terreus; the genus Bipolaris; the genus Blastomyces, such as Blastomyces dermatitidis; the genus Blumeria, such as Blumeria graminis; the genus Candida, such as Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, and Candida tropicalis; the genus Cladosporium, such as Cladosporium cladosporoides and Cladosporium herbarium; the genus Coccidioides, such as Coccidioides immitis and Coccidioides posadasii; and Colletotrichium trifolii. the genus Colletotrichium such as Cryptococcus neoformans; the genus Curvularia such as Curvularia lunata; the genus Encephalitozoon such as Encephalitozoon cuniculi; the genus Epicoccum such as Epicoccum nigrum; the genus Epidermophyton such as Epidermophyton floccosum; the genus Exophiala; the genus Exserohilum such as Exserohilum rostratum; the genus Fusarium such as Fusarium graminarium, Fusarium solani, and Fusarium sporotrichoides; the genus Fonsecaea such as Fonsecaea monophora; the genus Histoplasma such as Histoplasma capsulatum; the genus Leptosphaeria such as Leptosphaeria nodorum; the genus Malassezia such as Malassezia globosa; the genus Microsporum such as Microsporum canis; and the genus Mycosphaerella Mycosphaerella species such as Mycosphaerella graminicola; Neurospora species; Paecilomyces species such as Paecilomyces lilanicus and Paecilomyces varioti; Penicillium species such as Penicillium chrysogenum; Phytophthora species such as Phytophthora capsici and Phytophthora infestans; Plasmopara species such as Plasmopara viticola; Pneumocystis species such as Pneumocystis jirovecii; Pyricularia species such as Pyricularia oryzae; Pythium species such as Pythium ultimum; Puccinia species such as Puccinia coronata and Puccinia graminis; Rhizoctonia species such as Rhizoctonia solani; Rhizomucor species; Scedosporium species such as Fusarium apiospermum and Scedosporium prolificans; Scopulariopsis the genus Scopulariopsis such as Trichophyton brevicaulis; the genus Sporothrix such as Trichophyton schenckii; the genus Talaromyces such as Trichophyton marneffei, the genus Trichophyton such as Trichophyton mentagrophytes, Trichophyton interdigitale, Trichophyton rubrum, Trichophyton tonsurans, and Trichophyton verrucosum; the genus Trichophyton such as Trichosporon asahii and Trichosporon beigelii; the genus Ustilago, etc.
Among these, the antifungal agent of the present invention is suitable for use against the genus Aspergillus, Trichophyton or Candida, and is particularly suitable for use against Aspergillus fumigatus or Trichophyton tonsurans.

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

The medical/veterinary antifungal agent of the present invention can be applied to both systemic fungal infections and superficial fungal infections. Specific examples of fungal infections include aspergillosis, such as pulmonary aspergillosis and systemic aspergillosis (which is more likely to occur in immunosuppressed patients such as bone marrow recipients or AIDS patients), candida infections, such as systemic candidiasis, cryptococcal meningitis, rhinocerebral mucomycosis, pulmonary mucormycosis, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, lobomycosis, keratomycosis, sporotrichosis, chromoblastomycosis, chromomycosis, phaeohyphomycosis, zygomycosis, cryptococcosis, disseminated sporotrichosis, and ringworm. worm), tinea capitis (tinea pedis), tinea corporis (ringworm), tinea cruris (jock itch), tinea pedis (athlete's foot), tinea unguium (tinea unguium), candidiasis of the skin, mouth, or vagina, Malassezia, chronic mucocutaneous candidiasis, Pneumocystis pneumonia, and Marneffei penicilliosis.
The antifungal agent of the present invention can also be used to treat allergic diseases caused by fungi, such as allergic bronchopulmonary asthma (ABPA); asthma, rhinosinusitis, or sinusitis.

The medical/veterinary antifungal agent of the present invention may contain pharmaceutically acceptable additives. There are no particular limitations on the additives, as long as they are used in known medical drugs. These additives are naturally sterile and non-pyrogenic. Furthermore, additives can be selected appropriately 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 thereof include solid preparations such as tablets, powders, granules, capsules, troches (lozenges), and pellets; liquid preparations such as syrups, emulsions, suspensions, solutions, pour-on preparations, and spot-on preparations; semi-solid preparations such as ointments and gels; gaseous preparations such as aerosols and vapors; and nanoparticle preparations.
The medical antifungal agent of the present invention can be administered by known methods, including, for example, subcutaneous, intravenous, intramuscular, intrasternal (intrasternally) injection, transdermal administration such as insertion into the anus or vagina, or application, spraying, or dropping onto the skin surface, oral administration such as oral ingestion, and nasal administration such as inhalation.

In the case of solid dosage forms 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; diluents such as lactose, dextrose, sucrose, cellulose, corn starch, or potato starch; lubricants such as silica, talc, stearic acid, magnesium stearate or calcium stearate, or polyethylene glycol; binders such as starch, arabic gums, gelatin, methylcellulose, carboxymethylcellulose, or polyvinylpyrrolidone; disaggregating agents such as starch, alginic acid, alginates, or sodium starch glycolate; effervescing mixtures; colorants; sweeteners; wetting agents such as lecithin, polysorbates, or lauryl sulfate; or non-toxic, pharmacologically inactive substances commonly used in pharmaceutical formulations. These additives can be incorporated into the medical antifungal agent of the present invention by known methods such as mixing, granulation, tableting, sugar coating, or film coating.

In the case of liquid preparations for oral administration, additives that can be used in the medical/veterinary antifungal agent of the present invention include solubilizers such as cyclodextrin or modified cyclodextrin, sucrose, glycerin, mannitol, sorbitol, natural gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, or 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 sterilized water, olive oil, ethyl oleate, glycols such as propylene glycol, solubilizers such as cyclodextrin and modified cyclodextrin, etc. Furthermore, an appropriate amount of lidocaine hydrochloride can also be included if 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; solubilizers such as cyclodextrin and modified cyclodextrin; and the like. These can also be included in the form of a sterilized isotonic saline solution.

The amount of Compound (I) or a salt thereof contained in the antifungal agent for medical and veterinary use 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 method of administration, the type of infecting fungus, the age, body weight, symptoms of the patient, etc. For example, when administered orally or parenterally (by injection, drip infusion, etc.) to an adult, the agent can be administered at 0.1 to 100 mg/kg body weight once or several times a day.
Furthermore, the medical and 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 below by referring to synthesis examples, but the present invention is not limited to these examples.
Example 1
Synthesis of (E)-2-(5-(1-(isopropoxyimino)ethyl)-3-(2-methoxyphenethyl)-6-oxopyridazin-1(6H)-yl)-N-isopropylpropanamide (Step 1)
Synthesis of methyl 3-methoxy-6-((2-methoxyphenyl)ethynyl)pyridazine-4-carboxylate

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

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

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

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

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

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

3-Methoxy-6-(2-methoxyphenethyl)pyridazine-4-carboxylic acid (1.24 g) was dissolved in methylene chloride (20 ml), and N,O-dimethylhydroxylamine hydrochloride (0.50 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.06 g), 1-hydroxybenzotriazole monohydrate (0.07 g), and triethylamine (1.8 ml) were added thereto and stirred at room temperature overnight.
Water was poured into the reaction mixture, and the mixture was extracted with chloroform. The resulting organic layer was 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 1.15 g of the target product (yield 65%, three steps).
^{The 1} H-NMR spectrum of the target product obtained is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 7.21-7.16 (1H, m), 7.11-7.09 (2H, m), 6.86-6.83 (2H, m), 4.16 (3H, s), 3.82 (3H, s), 3.46 (3H, s), 3.35 (3H, s) 3.22-3.05 (4H, m).

(Step 5)
Synthesis of 1-(3-methoxy-6-(2-methoxyphenethyl)-pyridazine-4-yl)ethan-1-one

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

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

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

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

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

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

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

Example 2
Synthesis of (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-3-((2-methoxybenzyl)oxy)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl)isobutyramide (Step 1)
Synthesis of 1-(6-chloro-3-methoxypyridazine-4-yl)ethan-1-one O-isopropyl oxime

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

(Step 2)
Synthesis of (E)-1-(6-chloro-3-hydroxypyridazin-4-yl)ethan-1-one O-isopropyl oxime

1-(6-chloro-3-methoxypyridazin-4-yl)ethan-1-one O-isopropyloxime (0.45 g) was dissolved in N,N-dimethylformamide (8 ml), and p-toluenesulfonic acid monohydrate (1.76 g) and lithium chloride (0.39 g) were added to the solution, followed by stirring in an oil bath at 70°C for 2 hours.
After cooling to room temperature, water and saturated aqueous sodium bicarbonate were added, followed by extraction with ethyl acetate. The resulting ethyl acetate layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the resulting crude product was used directly in the next step.

(Step 3)
Synthesis of tert-butyl (S,E)-(1-(3-chloro-5-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl)carbamate

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

(Step 4)
Synthesis of (S,E)-2-(2-amino-3-methylbutyl)-6-chloro-4-(1-(isopropoxyimino)ethyl)pyridazin-3(2H)-one hydrochloride salt

Tert-butyl (S,E)-(1-(3-chloro-5-(1-isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl)carbamate (0.26 g) was dissolved in 1,4-dioxane (2 ml). To this was slowly added 4M hydrochloric acid-dioxane solution (6 ml), and the mixture was allowed to stand overnight at room temperature. The reaction mixture was then concentrated under reduced pressure, and the resulting crude product was used directly in the next step.

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

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

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

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

Some of the pyridazinone compounds of the present invention produced by methods similar to those in the above examples are shown in Table 1. The melting point (°C) or other physical properties of each compound are also shown in the table.

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

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

Some of the pyridazinone compounds of the present invention prepared by methods similar to those in the above examples are shown in Table 3. The table also lists the melting point (°C) or other physical properties of each compound. Some compounds are also shown to be mixtures of isomers.

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

Some of the pyridazinone compounds of the present invention prepared by methods similar to those in the above examples are shown in Table 5. The table also lists the melting point (°C) or other physical properties of each compound. Some compounds are also shown to be mixtures of isomers.

For some of the compounds in the table, retention times in liquid chromatography mass spectrometry (LCMS) are shown in Table 6.
The analytical conditions for liquid chromatography mass spectrometry (LCMS) were the above-mentioned Method (A) and also the following Method (C).
Method (C):
The HPLC system used was a Waters Alliance e2695 Separation Module, the single quadrupole MS detector (LC/MS) was an SQ Detector 2 (atmospheric pressure chemical ionization mode, PDA detection, manufactured by Waters), and the HPLC/UHPLC detector was a 2998 PDA Photodiode Array Detector (manufactured by Waters). The column was an XBridgeBEH C18 (manufactured by Waters, 2.1 x 50 mm, 2.5 μm), and the temperature was set to 40 °C. Water containing 0.1% formic acid was used as mobile phase (A), and acetonitrile was used as mobile phase (B). Mobile phase (A) and mobile phase (B) were passed through the column at a flow rate of 0.4 mL/min at the following concentrations, and the sample retention time (min) was measured with a sample injection volume of 6 μL.
The column inlet concentration of the mobile phase (B) was maintained at 30% by mass for 0.3 minutes from the time of sample injection, then increased at a constant rate from 30% by mass to 95% by mass over 1.7 minutes, maintained at 95% by mass for 1.5 minutes, and then reduced to 30% by mass in one go and maintained at 30% by mass for 2.5 minutes.

Some of the pyridazinone compounds of the present invention prepared by methods similar to those in the above examples are shown in Table 7. The physical properties of some of the compounds in the table are also shown. It is also indicated that some compounds are isomer mixtures.

For some of the compounds in the table, retention times in liquid chromatography mass spectrometry (LCMS) are shown in Table 8.
The analytical conditions for liquid chromatography mass spectrometry (LCMS) were the same as those of Method (A) described above.

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

[Biological Testing]
The usefulness of the pyridazinone compounds of the present invention as active ingredients of agricultural and horticultural fungicides will be demonstrated in the following test examples.
(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) were mixed and dissolved to obtain an emulsifiable concentrate (I) containing 5% of the active ingredient.

The control value was calculated using the following formula.

[Equation 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 emulsifiable concentrate (I) so that the pyridazinone compound concentration was 125 ppm, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto apple seedlings (cultivar "Orin", 3-4 leaf stage) grown in nursery pots. After air-drying, the apple seedlings were inoculated with conidia of the apple scab fungus (Venturia inaequalis) (treated group). As a control, apple seedlings that had not been sprayed with the drug solution were inoculated in the same manner (untreated group). These were then placed in a moist chamber at 20°C, with light and dark cycles alternating every 12 hours.
Two weeks after the inoculation, the leaves of the apple seedlings were visually observed to determine the lesion area ratio, and the control titer was calculated.
B-1, B-2, B-3, B-4, B-5, B-6, B-7, B-8, B-10, B-11, B-12, B-13, B-14, B-15, B-16, B -17, B-18, B-19, B-20, B-21, B-22, B-23, B-24, B-25, B-26, B-27, B-28, B-29, B-30 The compounds B-31, B-33, B-34, B-36, B-37, B-38, B-39, B-40, B-41, B-42, B-43, B-44, B-45, B-46, B-47, B-48, B-49, C-16, C-17, C-18, and C-19 were tested for apple scab control. All compounds showed a control rate of 75% or more.

(Test Example 2) Cucumber Gray Mold Control Test Water was added to Emulsifiable Concentrate (I) to a concentration of 125 ppm of the pyridazinone compound, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto cucumber seedlings (variety "Jihai", cotyledon stage) grown in seedling pots. After air-drying, a conidial suspension of Botrytis cinerea, the causative agent of cucumber gray mold, was dropwise inoculated onto the seedlings (treated group). As a control, cucumber seedlings not sprayed with the drug solution were dropwise inoculated onto the seedlings in the same manner as above (untreated group). The seedlings were then left to stand in a moist chamber at 20°C.
Four days after the inoculation, the leaves of the cucumber seedlings were visually observed to determine the lesion area rate and calculate the control titer.
Compounds B-2, B-4, B-5, B-10, B-11, B-17, B-33, B-36, B-37, B-39, B-40, B-47, C-16, and C-17 were tested for control of cucumber gray mold, and showed a control rate of 75% or more.

(Test Example 3) Wheat Powdery Mildew Control Test Water was added to Emulsifiable Concentrate (I) so that the pyridazinone compound concentration was 125 ppm, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto wheat seedlings (variety "Chihoku", 1- to 2-leaf stage) grown in seedling pots. After air-drying, the seedlings were inoculated by sprinkling conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) (treated group). As a control, wheat seedlings that had not been sprayed with the drug solution were inoculated in the same manner as above (untreated group). These were then left to stand in a greenhouse at 20°C.
Six days after the inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control titer was calculated.
Compounds B-5, B-6, B-8, B-9, B-10, B-11, B-12, B-13, B-14, B-15, B-16, B-17, B-18, B-19, B-20, B-21, B-22, B-23, B-24, B-25, B-26, B-27, B-28, B-33, B-34, B-36, B-37, B-38, B-39, B-40, B-41, B-42, B-43, B-44, B-45, B-46, B-47, B-48, C-17, and D-3 were tested for wheat powdery mildew control. All compounds showed 75% or higher control.

(Test Example 4) Wheat leaf rust control test Water was added to Emulsifiable concentrate (I) so that the pyridazinone compound concentration was 125 ppm, and the compound was dissolved to obtain a chemical solution. The chemical solution was then sprayed onto wheat seedlings (variety "Norin 61", 1-2 leaf stage) grown in seedling pots. After air drying, the wheat seedlings sprayed with the chemical solution were inoculated by dusting with uredospores of wheat leaf rust fungus (Puccinia recondita) (treated group). As a control, wheat seedlings not sprayed with the chemical solution were inoculated in the same manner as above (untreated group). They were then left to stand in a greenhouse at 20°C.
Twelve days after the inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio, and the control titer was calculated.
Compounds B-4, B-5, B-36, B-37, B-40, and B-47 were tested for wheat leaf rust control, and showed a control rate of 75% or more.

[Antibacterial test]
(Test Example) Antibacterial Test Against Fusarium graminearum Spores of Fusarium graminearum were added and dispersed in a glucose-supplemented Minimal SD Base medium, and then a pyridazinone compound dissolved in dimethyl sulfoxide was added to the medium to a concentration of 25 ppm. These were then dispensed onto a 96-well microplate and cultured in the dark at 25° C. for 3 days. After the culture, the turbidity at a wavelength of 405 nm was measured using a microplate reader, and the growth inhibition rate (%) of Fusarium graminearum was calculated in comparison with the untreated medium.
As a result, the following compounds showed an excellent growth inhibition rate of 50% or more.
Compound number: B-1, B-2, B-3, B-4, B-5, B-6, B-7, B-8, B-9, B-10, B-11, B-12, B- 13, B-14, B-15, B-16, B-17, B-18, B-19, B-20, B-21, B-22, B-24, B-25, B -26, B-27, B-28, B-29, B-30, B-33, B-34, B-36, B-37, B-38, B-39, B-40, B-41, B-43, B-44, B-45, B-46, B-47, B-50, B-53, C-16, C-17, C-18, C-19.

Claims (6)

A compound represented by formula (I) or a salt thereof:
[In formula (I),
Y represents an oxygen atom or a sulfur atom;
X ¹ represents a hydrogen atom;
X ² represents a group represented by R ¹ O—N═CR ⁶ —;
R ¹ and R ⁶ each independently represent a substituted or unsubstituted C1-6 alkyl group ;
^X3 is 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 alkynyl group, a group represented by R ¹ -CO-, 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, 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-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 -, R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-CO-NR ^N2 -, a group represented by R ^N1 -CS-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CS-NR ^N2 -, a group represented by R ^N1 SO ₂ -NR ^N2 - or a group represented by R ^N1 -C(═NR ^N1 )-NR ^N2 -,
R ^N1 and R ^N2 each independently represent 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, 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, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 , may together form a divalent organic group;
^X4 represents a group represented by Q-A-, a group represented by Q-A-B-, a group represented by Q-B-A-, a group represented by Q-SO ₂ -NR ^N3 -, a group represented by Q-C(R ⁷ )=N-, a group represented by Q-NR ^N3 -SO ₂ -, a group represented by Q-N=C(R ⁷ )- or a group represented by Q-B-;
each A independently represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or a carbonyl group;
B's each independently represent an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR ^N3 -, where R ^N3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a formyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group;
^R7 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group;
Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 10-membered heterocyclyl group. 10. An agricultural and horticultural fungicide comprising, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 and salts thereof . The agricultural and horticultural fungicide according to claim 2 , which is used for seed treatment. A nematicide comprising, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 and salts thereof . 10. An antifungal agent for medical or veterinary use, comprising as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and salts thereof . A compound represented by formula (II) or a salt thereof:
[In formula (II),
Y represents an oxygen atom or a sulfur atom;
X ¹ represents a hydrogen atom;
X ² represents a group represented by R ¹ O—N═CR ⁶ —;
R ¹ and R ⁶ each independently represent a substituted or unsubstituted C1-6 alkyl group ;
^X3 is 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 alkynyl group, a group represented by R ¹ -CO-, 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, 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-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 -, R ^N1 -CO-CO-NR ^N2 -, a group represented by R ^N1 -O-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CO-CO-NR ^N2 -, a group represented by R ^N1 -CS-NR ^N2 -, a group represented by R ^N1 R ^N1 N-CS-NR ^N2 -, a group represented by R ^N1 SO ₂ -NR ^N2 - or a group represented by R ^N1 -C(═NR ^N1 )-NR ^N2 -,
R ^N1 and R ^N2 each independently represent 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, 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, wherein R ^N1 and R ^N1 , or R ^N1 and R ^N2 , may together form a divalent organic group;
^X5 represents a group represented by HO-A-, a C1-6 alkoxycarbonyl group, or a halogeno group;
A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, a substituted or unsubstituted C3-6 cycloalkylene group, or a carbonyl group.