Pyridazinone compounds, agricultural and horticultural fungicides, nematicides, and medical and veterinary antifungals

Abstract

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

Description

[Technical Field]

[0001] 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. [Background technology]

[0002] Various compounds have been proposed that have activity for controlling crop diseases in agricultural and horticultural crop cultivation. In order for such compounds to be practically used as agricultural and horticultural fungicides, they must not only have sufficiently high efficacy but also be unlikely to develop fungicide resistance, not cause phytotoxicity to plants or soil contamination, and have low toxicity to livestock, fish, etc.

[0003] 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. [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] WO2021 / 085389A Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention aims to provide a pyridazinone compound that has excellent bactericidal and antibacterial activity, is 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 intended to provide a nematicide containing the compound as an active ingredient. It is also intended to provide an antifungal agent for medical and veterinary use containing the compound as an active ingredient. [Means for solving the problem]

[0006] As a result of extensive research into solving the above problems, the present inventors have completed the present invention, which includes the following aspects.

[0007] [1] A compound represented by formula (I) or a salt thereof: [ka]

[0008] In formula (I), Y represents an oxygen atom or a sulfur atom; X 1 , and X 2are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, 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 C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, cyano group, R 1 -CO- group, carboxy group, R 2 a group represented by -O-CO-, R 3 R 4 A group represented by N-, R 3 R 4 A group represented by N—CO—, R 1 a group represented by -CO-O-, R 1 -CO-NR 5 -, a group represented by R 2 a group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, a group represented by R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 -, a group represented by R 2 SO2-NR 5 -, a group represented by R 3 R 4 A group represented by N-SO2-, R 1 ON=CR 6 -, a group represented by R 3 R 4 NN=CR6 -, or R 1 -N=CR 6 - represents a group represented by the formula: R 1 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, R 2 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, R 3 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, R 4 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R 3 and R 4 may be taken together to form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R 6represents 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; X 3 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, R 1 a group represented by -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, R N1 A group represented by O-, R N1 a group represented by -CO-O-, R N1 a group represented by -O-CO-O-, R N1 R N1 A group represented by N-CO-O-, R N1 a group represented by -CS-O-, R N1 R N1 A group represented by N-CS-O-, R N1 R N2 A group represented by N-, R N1 -CO-NR N2 -, a group represented by R N1 -CO-CO-NR N2 -, a group represented by R N1 -O-CO-NR N2 -, a group represented by R N1 R N1 N-CO-NR N2 -, 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 SO2-NR N2 -, or R N1 -C(=NR N1 )-NRN2 - represents a group represented by R N1 , and R N2 each independently 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 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 QA-, a group represented by QAB-, a group represented by QBA-, a group represented by Q-SO2-NR N3 a group represented by QC(R 7 )=N-, a group represented by Q-NR N3 A group represented by -SO2-, QN=C(R 7 )- or QB-, 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 -NR N3 -, and 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, R 7 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.

[0009] [2] X 2 But R 1ON=CR 6 The compound or salt thereof according to [1], wherein R is a group represented by -. [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 used 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 salts thereof.

[0010] [7] A compound represented by formula (II) or a salt thereof: [ka]

[0011] In formula (II), Y represents an oxygen atom or a sulfur atom; X 1 and X 2are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, 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 C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, cyano group, R 1 -CO- group, carboxy group, R 2 a group represented by -O-CO-, R 3 R 4 A group represented by N-, R 3 R 4 A group represented by N—CO—, R 1 a group represented by -CO-O-, R 1 -CO-NR 5 -, a group represented by R 2 a group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, a group represented by R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 -, a group represented by R 2 SO2-NR 5 -, a group represented by R 3 R 4 A group represented by N-SO2-, R 1 ON=CR 6 -, a group represented by R 3 R 4 NN=CR6 -, or R 1 -N=CR 6 - represents a group represented by the formula: R 1 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, R 2 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, R 3 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, R 4 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R 3 and R 4 may be taken together to form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R 6represents 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; X 3 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, R 1 a group represented by -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, R N1 A group represented by O-, R N1 a group represented by -CO-O-, R N1 a group represented by -O-CO-O-, R N1 R N1 A group represented by N-CO-O-, R N1 a group represented by -CS-O-, R N1 R N1 A group represented by N-CS-O-, R N1 R N2 A group represented by N-, R N1 -CO-NR N2 -, a group represented by R N1 -CO-CO-NR N2 -, a group represented by R N1 -O-CO-NR N2 -, a group represented by R N1 R N1 N-CO-NR N2 -, 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 SO2-NR N2 -, or R N1 -C(=NR N1 )-NRN2 - represents a group represented by R N1 , and R N2 each independently 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 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 5 represents a group represented by HO-A-, a C 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] X 2 But R 1 ON=CR 6 The compound or salt thereof according to [7], wherein R is a group represented by -. [Effects of the Invention]

[0012] 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 low toxicity to humans, livestock, and fish. DETAILED DESCRIPTION OF THE INVENTION

[0013] [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). [ka]

[0014] 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.

[0015] 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 fluoro, chloro, bromo, and iodo groups; 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, 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; 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;

[0016] C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; C3-6 cycloalkenyl groups such as a 2-cyclopropenyl group, a 2-cyclopentenyl group, and a 3-cyclohexenyl group; C6-10 aryl groups such as phenyl and naphthyl groups; C6-10 aryl C1-6 alkyl groups such as benzyl and phenethyl groups; 3- to 6-membered heterocyclyl groups; 3- to 6-membered heterocyclyl C1-6 alkyl groups;

[0017] hydroxyl groups; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; C2-6 alkenyloxy groups such as vinyloxy, allyloxy, propenyloxy, and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy groups and propargyloxy groups; C6-10 aryloxy groups such as phenoxy and naphthoxy groups; C6-10 aryl C1-6 alkoxy groups such as benzyloxy groups and phenethyloxy groups;

[0018] carboxyl group; Formyl group; C1-6 alkylcarbonyl groups such as acetyl and propionyl groups; formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy and propionyloxy groups; 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;

[0019] 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 chloroacetyl, trifluoroacetyl, and trichloroacetyl groups;

[0020] amino group; C1-6 alkyl-substituted amino groups such as methylamino, dimethylamino, and diethylamino; C6-10 arylamino groups such as anilino groups and naphthylamino groups; C6-10 aryl C1-6 alkylamino groups such as benzylamino groups and phenethylamino groups;

[0021] Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino, propionylamino, butyrylamino, and i-propylcarbonylamino groups; 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, and an N-phenyl-N-methylaminocarbonyl group; imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino)ethyl group, and 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;

[0022] 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, and 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 vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio groups and propargylthio groups; 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 and a 2,2,2-trifluoroethylsulfinyl group; C2-6 alkenylsulfinyl groups such as allylsulfinyl groups; C2-6 alkynylsulfinyl groups such as propargylsulfinyl groups; C1-6 alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, and t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group; C2-6 alkenylsulfonyl groups such as allylsulfonyl groups; C2-6 alkynylsulfonyl groups such as propargylsulfonyl groups; aminothiocarbonyl group; C1-6 alkylsulfoximino groups such as S,S-dimethylsulfoximino groups;

[0023] tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl, triethylsilyl, and t-butyldimethylsilyl; triC6-10 aryl-substituted silyl groups such as triphenylsilyl groups; cyano group; nitro group;

[0024] 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.

[0025] The "3- to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms as ring-constituting atoms. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

[0026] 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.

[0027] 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.

[0028] [Y] Y represents an oxygen atom or a sulfur atom. In the present invention, Y is preferably an oxygen atom.

[0029] [X 1 and X 2 〕 X 1 and X 2are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, 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 C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, cyano group, R 1 -CO- group, carboxy group, R 2 a group represented by -O-CO-, R 3 R 4 A group represented by N-, R 3 R 4 A group represented by N—CO—, R 1 a group represented by -CO-O-, R 1 -CO-NR 5 -, a group represented by R 2 a group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, a group represented by R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR 5 -, a group represented by R 2 SO2-NR 5 -, a group represented by R 3 R 4 A group represented by N-SO2-, R 1 ON=CR 6 -, a group represented by R 3 R 4 NN=CR6 -, or R 1 -N=CR 6 - represents a group represented by the formula:

[0030] R 1 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. R 2 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 3 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. R 4 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. where R 3 and R 4 may be taken together to form a divalent organic group. R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 6represents 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.

[0031] X 1 , and X 2 Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0032] X 1 and X 2 The "C1-6 alkyl group" in X may be a straight chain or a branched chain. 1 Examples of the "C1-6 alkyl group" in the above formula 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.

[0033] X 1 and X 2 Examples of the "C2-6 alkenyl group" in the above formula 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-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.

[0034] X 1 and X 2Examples of the "C2-6 alkynyl group" in the above formula 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.

[0035] X 1 and X 2 Examples of the "C1-6 alkoxy group" in the above formula 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. X 1 and X 2 Examples of the "C2-6 alkenyloxy group" in the above formula include a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group. X 1 and X 2 Examples of the "C2-6 alkynyloxy group" in the above formula include an ethynyloxy group and a propargyloxy group.

[0036] X 1 and X 2 Examples of the "C1-6 alkylthio group" in the above formula 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. X 1 and X 2 Examples of the "C1-6 alkylsulfinyl group" in the above formula include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group. X 1 and X 2Examples of the "C1-6 alkylsulfonyl group" in the above formula include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.

[0037] X 1 and X 2In the above, examples of the 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" 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 butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; (C1-6 alkylideneamino)oxy groups such as (ethylideneamino)oxy group and propan-2-ylideneamino)oxy 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-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl 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, such as a 4-trifluoromethylphenyl group, a 4-trifluoromethoxyphenyl group, and 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, and 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.

[0038] X 1and X 2 Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. X 1 and X 2 Examples of the "C3-6 cycloalkyloxy group" in the above formula include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

[0039] X 1 and X 2 Examples of the "C6-10 aryl group" in the above formula include a phenyl group, a naphthyl group, an indanyl group, an indenyl group, and a tetralinyl group. X 1 and X 2 Examples of the "C6-10 aryloxy group" in the above formula include a phenoxy group and a naphthoxy group.

[0040] X 1 and X 2 Examples of the "C6-10 arylthio group" in the above formula include a phenylthio group and a naphthylthio group. X 1 and X 2 Examples of the "C6-10 arylsulfinyl group" in the above formula include a phenylsulfinyl group and a naphthylsulfinyl group. X 1 and X 2 Examples of the "C6-10 arylsulfonyl group" in the above formula include a phenylsulfonyl group and a naphthylsulfonyl group.

[0041] X 1 and X 2The "5- or 6-membered heterocyclyl group" in the above 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- or 6-membered heterocyclyl group" include 5- or 6-membered saturated heterocyclyl groups, 5- or 6-membered heteroaryl groups, and 5- or 6-membered partially unsaturated heterocyclyl groups.

[0042] 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.

[0043] X 1 and X 2 The "5- or 6-membered heterocyclyloxy group" in the above has a structure in which a 5- or 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.

[0044] X 1 and X 2In the formula (I), examples of the substituent 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" include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, C1-6 alkyl groups such as 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 groups; 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-dichlorobutoxy, C1-6 haloalkoxy groups such as trifluoromethoxy groups; C6-10 aryl groups such as phenyl groups and naphthyl groups; C6-10 aryl 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, such as 4-methylphenyl groups, 4-methoxyphenyl groups, 4-chlorophenyl groups, 4-trifluoromethylphenyl groups, and 4-trifluoromethoxyphenyl groups; pyrrolyl groups, furyl groups, thienyl groups, imidazoline groups, 5-membered heteroaryl groups such as 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 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; 6-membered heteroaryl groups 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. 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."

[0045] X 1 and X 2 "R" in 1 In the group represented by -CO-, 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.

[0046] R 1 Examples of the "C1-6 alkyl group" in the above formula 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. R 1 Examples of the "C2-6 alkenyl group" in the above formula include a vinyl group and a 1-propenyl group. R 1 Examples of the "C2-6 alkynyl group" in the above formula include an ethynyl group and a 1-propynyl group. R 1In the above, examples of the substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" 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, trifluoromethan C1-6 haloalkoxy groups such as oxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; C6-10 aryl groups such as phenyl group, naphthyl group; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloaryl groups such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc. 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, 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 haloalkoxy group, or a C1-6 haloalkoxy group; Preferred are a 5-membered heteroaryl group substituted by one or more substituents selected from a C1-6 alkyl group, a C1-6 haloalkoxy group, and a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, and 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.

[0047] R 1 Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. R 1Examples of the "C6-10 aryl group" in the above formula include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, and a tetralinyl group.

[0048] R 1 The "5- or 6-membered heterocyclyl group" in the above 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- or 6-membered heterocyclyl group" include 5- or 6-membered saturated heterocyclyl groups, 5- or 6-membered heteroaryl groups, and 5- or 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.

[0049] R 1In the above, examples of the substituent on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- or 6-membered heterocyclyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; 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; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl, and 1-fluoro-n-butyl groups; C1-6 haloalkyl groups such as 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; C6-10 aryl groups such as phenyl and naphthyl; 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, and 4-trifluoromethylphenyl. 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, 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, 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 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 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 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; 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.

[0050] "R 1 Specific examples of the "group represented by --CO--" include a formyl group, an acetyl group, a propionyl group, a butyryl group, and an i-propylcarbonyl group.

[0051] X 1 and X 2 "R" in 2 In the group represented by -O-CO-, 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. R 2 Specific examples of the substituents in 1 The same examples as those given above can be mentioned.

[0052] "R 2 Specific examples of the "group represented by --O--CO--" include a methoxycarbonyl group, an ethoxycarbonyl group, and a t-butoxycarbonyl group.

[0053] X 1 and X 2 "R" in 3 R 4 In the group represented by N-, 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; R 4 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 3 or R 4 Specific examples of the substituents in 1The same examples as those given above can be mentioned.

[0054] where R 3 and R 4 may be taken 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 alkyleneoxyC1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or "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.

[0055] "R 3 R 4 Specific examples of the "group represented by N-" include an amino group, a methylamino group, a dimethylamino group, and an i-propylamino group.

[0056] X 1 and X 2 "R" in 3 R 4 In the group represented by N-CO-, R 3 and R 4 is the above "R 3 R 4 The meanings are the same as those in "a group represented by N-". "R 3 R 4Specific examples of the "group represented by 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.

[0057] X 1 and X 2 "R" in 1 In the group represented by -CO-O-, R 1 is the above "R 1 The meaning is the same as that of the group represented by -CO-. "R 1 Specific examples of the "group represented by --CO--O--" include an acetyloxy group and an i-propylcarbonyloxy group.

[0058] X 1 and X 2 "R" in 1 -CO-NR 5 In the group represented by "-", R 1 is the above "R 1 The meaning is the same as that of the group represented by -CO-. R 5 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 5 Specific examples of the substituents in 1 The same examples as those given above can be mentioned. "R 1 -CO-NR 5 Specific examples of the "group represented by -" include an acetylamino group and an i-propylcarbonylamino group.

[0059] X 1 and X 2 "R" in 2 In the group represented by -O-CO-O-, R 2 is the above "R 2 -O-CO-" has the same meaning as that in "a group represented by -O-CO-". "R 2Specific examples of the "group represented by --O--CO--O--" include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

[0060] X 1 and X 2 "R" in 2 -O-CO-NR 5 In the group represented by "-", R 2 is the above "R 2 -O-CO- group" has the same meaning as that in "R 5 is the above "R 1 -CO-NR 5 - has the same meaning as that in "a group represented by -". "R 2 -O-CO-NR 5 Specific examples of the "group represented by -" include a methoxycarbonylamino group.

[0061] X 1 and X 2 "R" in 3 R 4 In the group represented by N-CO-O-, R 3 and R 4 is the above "R 3 R 4 The meanings are the same as those in "a group represented by N-". "R 3 R 4 Specific examples of the "group represented by N-CO-O-" include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.

[0062] X 1 and X 2 "R" in 3 R 4 N-CO-NR 5 In the group represented by "-", R 3 and R 4 is the above "R 3 R 4 R has the same meaning as in "a group represented by N-" 5 is the above "R 1 -CO-NR5 - has the same meaning as that in "a group represented by -". "R 3 R 4 N-CO-NR 5 Specific examples of the "group represented by -" include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.

[0063] X 1 and X 2 "R" in 2 SO2-NR 5 In the group represented by "-", R 2 is the above "R 2 -O-CO- group" has the same meaning as that in "R 5 is the above "R 1 -CO-NR 5 - has the same meaning as that in "a group represented by -". "R 2 SO2-NR 5 Specific examples of the "group represented by -" include a methanesulfonylamino group.

[0064] X 1 and X 2 "R" in 3 R 4 In the group represented by N-SO2-, R 3 and R 4 is the above "R 3 R 4 The meanings are the same as those in "a group represented by N-". "R 3 R 4 Specific examples of the "group represented by N-SO2-" include an N,N-dimethylaminosulfonyl group.

[0065] X 1 and X 2 "R" in 1 ON=CR 6 In the group represented by "-", R 1 is the above "R 1 The meaning is the same as that of the group represented by -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. R 6 Specific examples of the "substituted or unsubstituted C1-6 alkyl group" or "substituted or unsubstituted 5- or 6-membered heterocyclyl group" in 1 The same examples as those given above can be mentioned. R 6 Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group. R 6 Examples of the "mono C1-6 alkylamino group" in the "substituted or unsubstituted mono C1-6 alkylamino group" include a methylamino group, an ethylamino group, and an i-propylamino group. R 6 Examples of the "di-C1-6 alkylamino group" in the "substituted or unsubstituted di-C1-6 alkylamino group" include a dimethylamino group, a diethylamino group, and an N-methyl-Ni-propylamino group. R 6 Examples of the "C1-6 alkoxy group" in the "substituted or unsubstituted C1-6 alkoxy group" 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, and an i-hexyloxy group. R 6 Examples of the "C1-6 alkylthio group" in the "substituted or unsubstituted C1-6 alkylthio group" 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. R 6In the above, the substituents on the "C1-6 alkoxy group", "mono-C1-6 alkylamino group", "di-C1-6 alkylamino group", or "C1-6 alkylthio group" include R 1 In the above, examples of the substituent on the "C1-6 alkyl group" include the same substituents as those exemplified above. "R 1 ON=CR 6 Specific examples of the "group represented by -" include a 1-(i-propoxyimino)ethyl group.

[0066] X 1 and X 2 "R" in 3 R 4 NN=CR 6 In the group represented by "-", R 3 and R 4 is the above "R 3 R 4 R has the same meaning as in "a group represented by N-" 6 is the above "R 1 ON=CR 6 - has the same meaning as that in "a group represented by -".

[0067] X 1 and X 2 "R" in 1 -N=CR 6 In the group represented by "-", R 1 and R 6 is the above "R 1 ON=CR 6 - has the same meaning as that in "a group represented by -".

[0068] In the present invention, preferred X 1 Examples of the alkyl group include a hydrogen atom and a substituted or unsubstituted C1-6 alkyl group. Preferred X 2 As for "R 1 ON=CR 6 Examples of the group include "a group represented by -".

[0069] [X 3 〕 X 3 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, R 1 It represents a group represented by -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.

[0070] X 3 Examples of the "straight chain C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group. X 3 Examples of the "straight-chain C2-6 alkenyl group" in the above formula 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. X 3 Examples of the "straight-chain C2-6 alkynyl group" in the above formula 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. X 3 Examples of the "four-membered heterocyclyl group" in the above formula include an azetidinyl group and an oxetanyl group. X 3 Specific examples of other substituents in 1 and X 2 The same examples as those given above can be mentioned.

[0071] In the present invention, preferred X 3 Examples of the alkyl group include a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, and a substituted or unsubstituted C6-10 aryl group. In the present invention, more preferred X 3 The alkyl group is a substituted linear C1-6 alkyl group.

[0072] 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. The substituent groups are shown below. 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 a 3-6 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 3-10 membered heterocyclyl group, a substituted or unsubstituted 3-10 membered heterocyclyloxy group, a nitro group, a cyano group, R a -CO- group, carboxy group, R b a group represented by -O-CO-, R c R d A group represented by N-, R c R d A group represented by N—CO—, R c R d N-NR da group represented by -CO-, R b SO2-NR d a group represented by -CO-, R a a group represented by -CO-O-, 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 a group represented by -CO-, R b a group represented by -O-CO-O-, R b -O-CO-NR e -, a group represented by R c R d A group represented by 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 SO2-NR e -, a group represented by R c R d A group represented by N-SO2-, R a ON=CR f -, a group represented by R h R j A group represented by C=NO-, R a -C(=NR g )-NR e -, a group represented by R c R d NC(=NR g )-, R h R i A group represented by S(=O)=N-CO-, R h R i A group represented by S=N—CO—.

[0073] In the above substituent group, R a 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 3-10 membered heterocyclyl group. R b each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- or 6-membered heterocyclyl group. R c 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. R d each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group, where R c and R d may be taken together to form a divalent organic group. R e each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group. R f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group. R g each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R heach independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R i each independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group, where R h and R i may be taken together to form a divalent organic group.

[0074] Examples of the "halogeno group" in G include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0075] 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.

[0076] Examples of the "C2-6 alkenyl group" for G 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-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.

[0077] Examples of the "C2-6 alkynyl group" for G 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.

[0078] Examples of the "C1-6 alkoxy group" in 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" in G include a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group. Examples of the "C2-6 alkynyloxy group" in G include an ethynyloxy group and a propargyloxy group.

[0079] Examples of the "C1-6 alkylthio group" in 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.

[0080] 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 group, chloro group, bromo group, and iodo group; hydroxyl group; C1-6 alkyl groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, and t-butoxy group. 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-methylfuran 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, such as a phenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, and 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, and a tetrazolyl group a 5-membered heteroaryl group such as; 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, and 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.

[0081] Examples of the "C3-6 cycloalkyl group" in G include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the "C3-6 cycloalkyloxy group" in G include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

[0082] Examples of the "C6-10 aryl group" in G include a phenyl group and a naphthyl group. Examples of the "C6-10 aryloxy group" in G include a phenoxy group and a naphthoxy group.

[0083] Examples of the "C6-10 arylthio group" in 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" in G include a phenylsulfonyl group and a naphthylsulfonyl group.

[0084] 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.

[0085] 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; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; 9-membered heteroaryl groups such as indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, and benzisothiazolyl; and 10-membered heteroaryl groups such as quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, and quinoxalinyl. 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.

[0086] The "3- to 10-membered heterocyclyloxy group" in G has a structure in which a 3- to 10-membered heterocyclyl group and an oxy group are bonded together. Specific examples include a thiazolyloxy group and a pyridyloxy group.

[0087] 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 a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i- C1-6 alkyl groups such as 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; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, and t-butoxy; C1-6 haloalkyl groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy. an alkoxy group; a C3-6 cycloalkyl C1-6 alkoxy group; a C6-10 aryl C1-6 alkoxy group; a (C6-10 aryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkoxy group; a 5-membered heteroaryl C1-6 alkoxy group; a (5-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) Heteroaryl) C1-6 alkoxy groups; 6-membered heteroaryl C1-6 alkoxy groups; (6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group) C1-6 alkoxy groups; C1-6 alkylthio groups such as a methylthio group and an ethylthio 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 trifluoromethylthio group and 2,2,2-trifluoroethylthio group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; C3-6 cycloalkyl groups such as cyclopropyl group and cyclobutyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloa C3-6 cycloalkyl groups substituted with one or more substituents of alkyl groups, C1-6 haloalkoxy groups, or cyano groups; C3-6 cycloalkenyl groups; C6-10 aryl groups such as phenyl groups and naphthyl groups; and substituted with one or more of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups such as 4-methylphenyl groups, 4-methoxyphenyl groups, 4-chlorophenyl groups, 4-trifluoromethylphenyl groups, and 4-trifluoromethoxyphenyl groups. a C6-10 aryl group substituted by a group; a 3- or 4-membered saturated heterocyclyl group 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 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 pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, or a dioxolanyl group , dioxanyl groups and other 5- or 6-membered saturated heterocyclyl groups; 5- or 6-membered saturated heterocyclyl groups 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; 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups;5-membered heteroaryl groups 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; 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 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; pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, partially unsaturated 5-membered heterocyclyl groups such as a nyl group, oxazolinyl group, or isoxazolinyl group; partially saturated 5-membered heterocyclyl groups 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; partially unsaturated 6-membered heterocyclyl groups such as a dihydropyranyl group; partially saturated 6-membered heterocyclyl groups 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; R G1 A group represented by —CO— (wherein R G1represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted by 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 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 alkyl group; (a 5- or 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 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2- and R represents a C6-6 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- or 6-membered heteroaryl group; or a 5- or 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. G1 The same applies to ); carboxyl group; R G2 A group represented by —O—CO— (wherein R G2represents a C1-6 alkyl group; a C1-6 alkyl group substituted by 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 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 alkyl group; (a 5- or 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 alkyl group; a C2-6 alkenyl group; or 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- or 6-membered heteroaryl group; or a 5- or 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. G2 The same applies to ); R G1 R G1 A group represented by N- (R G1 may be the same or different. G1 may combine 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— (R in the formula G1 may be the same or different. G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R G1 A group represented by -CO-O-; 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 selected from 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 selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; or a (5- or 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group. G3 The same applies to ); R G2 A group represented by -O-CO-O-; R G2 -O-CO-NR G3 -; R G1 R G1 A group represented by N—CO—O— (R in the formula G1 may be the same or different. G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R G1 R G1 N-CO-NR G3 - (wherein R G1 may be the same or different. G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. );R G2 SO2-NR G3 -; R G1 R G1 A group represented by N-SO2- (R in the formula G1 may be the same or different. G1may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R G1 -ON=C(R G4 )- (wherein R G4 represents a hydrogen atom or a C1-6 alkyl group; (R G1 )2C=NO- (wherein R G1 may be the same or different. G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; A pentafluorosulfanyl group, a nitro group, or a cyano group is preferred. Furthermore, 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."

[0088] "R" in G a In the group represented by -CO-, 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 3-10 membered heterocyclyl group.

[0089] R a Examples of the "C1-6 alkyl group" in the above formula 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. R a Examples of the "C2-6 alkenyl group" in the above formula include a vinyl group and a 1-propenyl group. R aExamples of the "C2-6 alkynyl group" in the above formula include an ethynyl group and a 1-propynyl group. R aIn the above, examples of the substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" 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 methylsulfonyl and ethylsulfonyl; C1-6 alkylsulfonyl groups such as methylsulfonyl and ethylsulfonyl; carboxy groups; C1-6 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, and t-butoxycarbonyl; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; C6-10 aryl groups such as phenyl and naphthyl. a C6-10 aryl 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, 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, 5-membered heteroaryl groups such as a aryl group or a tetrazolyl group; 5-membered heteroaryl groups 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; 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 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;Alternatively, a cyano group is preferred.

[0090] R a Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. R a Examples of the "C6-10 aryl group" in the above formula include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, and a tetralinyl group.

[0091] R a The "3- to 10-membered heterocyclyl group" in the above means 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; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; 9-membered heteroaryl groups such as indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, and benzisothiazolyl; and 10-membered heteroaryl groups such as quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, and quinoxalinyl. 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.

[0092] R aIn the above, examples of the substituent on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "3- to 10-membered heterocyclyl group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; 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; C1-6 haloalkanes such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, and 1-fluoro-n-butyl groups; alkyl 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; C3-6 cycloalkyl C1-6 alkoxy groups; C6-10 aryl C1-6 alkoxy groups; (any of C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups) a C6-10 aryl substituted by one or more substituents)C1-6 alkoxy group; a 5-membered heteroaryl C1-6 alkoxy group; a (5-membered heteroaryl 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)C1-6 alkoxy group; a 6-membered heteroaryl C1-6 alkoxy group; a (5-membered heteroaryl 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 substituted with a C1-6 alkoxy group; a C1-6 alkylthio group such as a methylthio group, an ethylthio group; a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group; a C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group; a C1-6 haloalkylthio group such as a trifluoromethylthio group, a 2,2,2-trifluoroethylthio group; a C1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group;C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl and 2,2,2-trifluoroethylsulfonyl; C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl and cyclopentyl; C3-6 cycloalkyl groups substituted with one or more substituents selected from C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, C1-6 haloalkoxy groups and cyano groups; C3-6 cycloalkenyl groups; C6-10 aryl groups such as phenyl and naphthyl; 4-methylphenyl groups, 4-methylphenyl groups, a C6-10 aryl 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, such as an oxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, and a 4-trifluoromethoxyphenyl group; a 3- or 4-membered saturated heterocyclyl group such as an aziridinyl group, an epoxy group, an azetidinyl group, and an oxetanyl 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 3- or 4-membered saturated heterocyclyl group substituted by one or more substituents selected from the group consisting of alkoxy groups; 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 selected from the group consisting 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 5-membered heteroaryl groups such as thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; 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;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; 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, and 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, and a C1-6 haloalkoxy group; R q1 A group represented by —CO— (wherein R q1represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted by 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 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 alkyl group; (a 5- or 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 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2- and R represents a C6-6 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- or 6-membered heteroaryl group; or a 5- or 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. q1 The same applies to ); carboxyl group; R q2 A group represented by —O—CO— (wherein R q2is a C1-6 alkyl group; a C1-6 alkyl group substituted by 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 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 alkyl group; (a 5- or 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 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 aryl R represents 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- or 6-membered heteroaryl group; or a 5- or 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. q2 The same applies to R q1 R q1 A group represented by N- (R q1 may be the same or different. q1 may combine 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— (R in the formula q1 may be the same or different. q1may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R q1 A group represented by -CO-O-; 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 selected from 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 selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; or a (5- or 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group. q3 The same applies to R q2 A group represented by -O-CO-O-; R q2 -O-CO-NR q3 -; R q1 R q1 A group represented by N—CO—O— (R in the formula q1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R q1 R q1 N-CO-NR q3 - (wherein R q1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. );R q2 SO2-NR q3 -; R q1 R q1 A group represented by N-SO2- (R in the formulaq1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R q1 -ON=C(R q4 )- (wherein R q4 represents a hydrogen atom or a C1-6 alkyl group; (R q1 )2C=NO- (wherein R q1 may be the same or different. q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; A pentafluorosulfanyl group, a nitro group, or a cyano group is preferred. Furthermore, as a substituent on the "C3-6 cycloalkyl group" or the "3- to 10-membered heterocyclyl group", an oxo group is also preferred.

[0093] "R a Specific examples of the "group represented by --CO--" include a formyl group, an acetyl group, and an i-propylcarbonyl group.

[0094] "R" in G b In the group represented by -O-CO-, 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. R b Specific examples of the substituents in a The same examples as those given above can be mentioned.

[0095] "R bSpecific examples of the "group represented by --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.

[0096] "R" in G c R d In the group represented by N-, 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; 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. R c or R d Specific examples of the substituents in a The same examples as those given above can be mentioned. R d Examples of the "C1-6 alkoxy group" in the above formula 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. R dIn the above, examples of the substituent on the "C1-6 alkoxy group" 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 a cyclohexyl group; C6-10 aryl groups such as a phenyl group or a naphthyl group; C6-10 aryl 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, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, and a 4-trifluoromethoxyphenyl group; or a cyano group.

[0097] where R c and R d may be taken 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 -CH2CH2-Si(CH3)2-CH2CH2-. Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, and a tetramethylene group. Examples of the "C1-3 alkyleneoxyC1-3 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.

[0098] "R c R d Specific examples of the "group represented by N-" include an amino group, a methylamino group, a dimethylamino group, and an i-propylamino group.

[0099] "R" in G c R d In the group represented by N-CO-, R c and R d is the above "R c R d The meanings are the same as those in "a group represented by N-". "R c R d Specific examples of the "group represented by 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.

[0100] "R" in G c R d N-NR d In the group represented by -CO-, R c and R dis the above "R c R d The meanings are the same as those in "a group represented by N-". "R c R d N-NR d Specific examples of the "group represented by --CO--" include a 2,2-dimethylhydrazine-1-carbonyl group.

[0101] "R" in G b SO2-NR d In the group represented by -CO-, R b is the above "R b -O-CO- group" and R d is the above "R c R d The meaning is the same as that in "a group represented by N-". "R b SO2-NR d Specific examples of the "group represented by --CO--" include a (methylsulfonyl)carbamoyl group, a (cyclopropylsulfonyl)carbamoyl group, a ((1-methylcyclopropyl)sulfonyl)carbamoyl group, and the like.

[0102] "R" in G a In the group represented by -CO-O-, R a is the above "R a The meaning is the same as that of the group represented by -CO-. "R a A specific example of the "group represented by --CO--O--" is an acetyloxy group.

[0103] "R" in G a -CO-NR e In the group represented by "-", R a is the above "R a The meaning is the same as that of the group represented by -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. R e Specific examples of the substituents in a The same examples as those given above can be mentioned. "R a -CO-NR e Specific examples of the "group represented by -" include an acetylamino group, a propionylamino group, a butyrylamino group, and an i-propylcarbonylamino group.

[0104] "R" in G a -CO-CO-NR e In the group represented by "-", R a is the above "R a -CO- group" has the same meaning as that in "R e is the same as the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". "R a -CO-CO-NR e Specific examples of the "group represented by -" include an oxopropanamide group.

[0105] "R" in G a -CO-NR e -NR e In the group represented by "-", R a is the above "R a -CO- group" has the same meaning as that in "R e is the same as the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". "R a -CO-NR e -NR e Specific examples of the "group represented by -" include an acetylhydrazinyl group, an i-propylcarbonylhydrazinyl group, and the like.

[0106] "R" in G a -CO-NR e -NR e In the group represented by -CO-, R ais the above "R a -CO- group" has the same meaning as that in "R e is the same as the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". "R a -CO-NR e -NR e A specific example of the "group represented by --CO--" is a 2-acetylhydrazine-1-carbonyl group.

[0107] "R" in G b In the group represented by -O-CO-O-, R b is the above "R b -O-CO-" has the same meaning as that in "a group represented by -O-CO-". "R b Specific examples of the "group represented by --O--CO--O--" include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

[0108] "R" in G b -O-CO-NR e In the group represented by "-", R b is the above "R b -O-CO- group" has the same meaning as that in "R e is the above "R b -CO-NR e - has the same meaning as that in "a group represented by -". "R b -O-CO-NR e Specific examples of the "group represented by -" include a methoxycarbonylamino group.

[0109] "R" in G c R d In the group represented by N-CO-O-, R c and R d is the above "R c R d The meanings are the same as those in "a group represented by N-". "R c Rd Specific examples of the "group represented by N-CO-O-" include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.

[0110] "R" in G c R d N-CO-NR e In the group represented by "-", R c and R d is the above "R c R d R has the same meaning as in "a group represented by N-" e is the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". "R c R d N-CO-NR e Specific examples of the "group represented by -" include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.

[0111] "R" in G c R d N-CO-CO-NR e In the group represented by "-", R c and R d is the above "R c R d R has the same meaning as in "a group represented by N-" e is the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". "R c R d N-CO-CO-NR e Specific examples of the "group represented by -" include a 2-(methylamino)-2-oxoacetamide group, a 2-(t-butylamino)-2-oxoacetamide group, and the like.

[0112] "R" in G a -CS-NR e In the group represented by "-", R a is the above "Ra -CO- group" has the same meaning as that in "R e is the same as the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". "R a -CS-NR e Specific examples of the "group represented by -" include an ethanethioamide group, a propanethioamide group, and a 2-methylpropanethioamide group.

[0113] "R" in G c R d N-CS-NR e In the group represented by "-", R c and R d is the above "R c R d R has the same meaning as in "a group represented by N-" e is the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". "R c R d N-CS-NR e Specific examples of the "group represented by -" include a 3,3-dimethylthioureido group.

[0114] "R" in G b SO2-NR e In the group represented by "-", R b is the above "R b -O-CO- group" has the same meaning as that in "R e is the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". "R b SO2-NR e Specific examples of the "group represented by -" include a methanesulfonylamino group.

[0115] "R" in G c R dIn the group represented by N-SO2-, R c and R d is the above "R c R d The meanings are the same as those in "a group represented by N-". "R c R d Specific examples of the "group represented by N-SO2-" include an N,N-dimethylaminosulfonyl group.

[0116] "R" in G a ON=CR f In the group represented by "-", R a is the above "R a The meaning is the same as that of the group represented by -CO-. R f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group. R f Specific examples of the substituents in a The same examples as those given above can be mentioned. "R a ON=CR f Specific examples of the "group represented by -" include a (hydroxyimino)methyl group and an (ethoxyimino)methyl group.

[0117] "R" in G a -C(=NR g )-NR e In the group represented by "-", R a is the above "R a -CO- group" has the same meaning as that in "R e is the above "R a -CO-NR e - has the same meaning as that in "a group represented by -". R g each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R g Specific examples of the substituents in aThe same examples as those given above can be mentioned.

[0118] "R" in G c R d NC(=NR g )-" in which R c and R d is the above "R c R d R has the same meaning as in "a group represented by N-" g is the above "R a -C(=NR g )-NR e - has the same meaning as that in "a group represented by -".

[0119] "R" in G h R i In the group represented by S(=O)=N-CO-, R h each independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group, R i each independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R h or R i Specific examples of the substituents in a The same examples as those given above can be mentioned.

[0120] where R h and R i may be taken 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 alkyleneoxyC1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or "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.

[0121] "R" in G h R i In the group represented by S=N-CO-, R h or R i is the above "R h R i The meanings are the same as those in "a group represented by S(=O)=N-CO-".

[0122] "R" in G h R j In the group represented by C=NO-, R h and R j is the above "R h R j It has the same meaning as that in "a group represented by S=NO-". "R h R j Specific examples of the "group represented by C=NO-" include a (propan-2-ylideneamino)oxy group.

[0123] 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 alkyleneoxyC1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on a "C1-5 alkylene group," "oxyC1-4 alkylene group," "oxyC2-3 alkyleneoxy group," and "C1-3 alkyleneoxyC1-3 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.

[0124] 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 3-10 membered heterocyclyl group, R b a group represented by -O-CO-, R c R d A group represented by N-, R c R d A group represented by N—CO—, R a a group represented by -CO-O-, R a -CO-NR e -, a group represented by R b -O-CO-NR e -, a group represented by R c R d A group represented by N-CO-O-, R c R d N-CO-NR e-, a group represented by R c R d N-CS-NR e -, a group represented by R b SO2-NR e -, a group represented by R a ON=CR f -, or R h R i Examples include a group represented by C=NO-.

[0125] [X above 3 Other than X 3 and R N1 , R N2 〕 Additionally, X 3 is R N1 A group represented by O-, R N1 a group represented by -CO-O-, R N1 a group represented by -O-CO-O-, R N1 R N1 A group represented by N-CO-O-, R N1 a group represented by -CS-O-, R N1 R N1 A group represented by N-CS-O-, R N1 R N2 A group represented by N-, R N1 -CO-NR N2 -, a group represented by R N1 -CO-CO-NR N2 -, a group represented by R N1 -O-CO-NR N2 -, a group represented by R N1 R N1 N-CO-NR N2 -, 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 SO2-NR N2 -, or R N1 -C(=NR N1 )-NR N2- represents a group represented by the formula:

[0126] R N1 , and R N2 each independently 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 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 be taken together to form a divalent organic group.

[0127] R N1 , and R N2 Examples of the "straight chain C1-6 alkyl group" in the above formula include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, and an n-hexyl group. R N1 , and R N2 Examples of the "straight-chain C2-6 alkenyl group" in the above formula 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. R N1 , and R N2 Examples of the "straight-chain C2-6 alkynyl group" in the above formula 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. R N1 , and R N2 Examples of the "four-membered heterocyclyl group" in the above formula include an azetidinyl group and an oxetanyl group. R N1 , and R N2Specific examples of other substituents in 1 The same examples as those given above can be mentioned.

[0128] [X 4 〕 X 4 represents a group represented by QA-, a group represented by QAB-, a group represented by QBA-, a group represented by Q-SO2-NR N3 a group represented by QC(R 7 )=N-, a group represented by Q-NR N3 A group represented by -SO2-, QN=C(R 7 )- or QB-.

[0129] [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.

[0130] Examples of the "C1-6 alkylene group" in A include a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group. Examples of the "C2-6 alkenylene group" in A include a vinylene group (-CH=CH-), a divinylene group (-CH=CH-CH=CH-), a propenylene group (-CH=CH-CH2-, -CH2-CH=CH-), and the like. Examples of the "C2-6 alkynylene group" in A include an ethynylene group (-C≡C-), a propynylene group (-CH2-C≡C-, -C≡C-CH2-), 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.

[0131] In the present invention, preferred examples of A include a substituted or unsubstituted C1-6 alkylene group and 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. The substituent groups are shown below. 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 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 a1 -CO- group, carboxy group, R b1 a group represented by -O-CO-, R c1 R d1 A group represented by N-, R c1 R d1 A group represented by N—CO—, R a1 a group represented by -CO-O-, R a1 -CO-NR e1 -, a group represented by R b1 a group represented by -O-CO-O-, R b1 -O-CO-NR e1 -, a group represented by R c1 R d1 A group represented by N-CO-O-, R c1 R d1 N-CO-NR e1-, a group represented by R b1 SO2-NR e1 -, a group represented by R c1 R d1 A group represented by N-SO2-, R a1 ON=CR f1 -, a group represented by R g1 R h1 Groups represented by C=NO-, oxo group (O=), thioxo group (S=), R a1 a divalent group represented by -N=, R a1 A divalent group represented by ON=, R c1 R d1 A divalent group represented by NN=, R a1 -CO-NR e1 a divalent group represented by -N=, R b1 -O-CO-NR e1 a divalent group represented by -N=, R b1 SO2-NR e1 A divalent group represented by -N=.

[0132] In the above substituent group, R a1 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, R b1 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, R c1 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, R d1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R c1 and R d1 may be taken 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, where R g1 and R h1 may be taken together to form a divalent organic group.

[0133] Examples of the "halogeno group" in Ga include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0134] The "C1-6 alkyl group" in Ga may be linear or branched. Examples of the "C1-6 alkyl group" in Ga 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, an t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, and an i-hexyl group.

[0135] Examples of the "C2-6 alkenyl group" for Ga 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-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, and a 5-hexenyl group.

[0136] Examples of the "C2-6 alkynyl group" for Ga 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.

[0137] Examples of the "C1-6 alkoxy group" in 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, a 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.

[0138] 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.

[0139] 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 group, chloro group, bromo group, and iodo group; hydroxyl group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, and t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichloro-n-propoxy group, 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 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, such as 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl and 4-trifluoromethoxyphenyl; and cyano groups.

[0140] Examples of the "C3-6 cycloalkyl group" in 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.

[0141] Examples of the "C6-10 aryl group" in 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" in Ga include a phenoxy group and a naphthoxy group.

[0142] 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.

[0143] The "3- to 6-membered heterocyclyl group" in Ga is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, 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 "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.

[0144] 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.

[0145] 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 together. Specific examples include a thiazolyloxy group and a pyridyloxy group.

[0146] Examples of the substituent 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 group, chloro group, bromo group, and iodo group; C1-6 alkyl groups such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, and n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, and 1-fluoro-n-butyl group. Preferred are a C1-6 haloalkyl 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 C6-10 aryl group substituted by one or more substituents, either 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; or a cyano group.

[0147] "R" in Ga a1 In the group represented by -CO-, 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.

[0148] R a1Examples of the "C1-6 alkyl group" in the above formula 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. R a1 Examples of the "C2-6 alkenyl group" in the above formula include a vinyl group and a 1-propenyl group. R a1 Examples of the "C2-6 alkynyl group" in the above formula include an ethynyl group and a 1-propynyl group. R a1 In the above, examples of the substituent on the "C1-6 alkyl group," "C2-6 alkenyl group," or "C2-6 alkynyl group" 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; Preferred are 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 selected from halogeno groups, C1-6 haloalkyl groups, and C1-6 haloalkoxy groups, such as 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl groups; and cyano groups.

[0149] R a1 Examples of the "C3-6 cycloalkyl group" in the above formula include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. R a1 Examples of the "C6-10 aryl group" in the above formula include a phenyl group and a naphthyl group.

[0150] R a1The "5- or 6-membered heterocyclyl group" in the above 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- or 6-membered heterocyclyl group" include 5- or 6-membered saturated heterocyclyl groups, 5- or 6-membered heteroaryl groups, and 5- or 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.

[0151] R a1Examples of substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- or 6-membered heterocyclyl group" in the formula (I) 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; Preferred are C1-6 alkoxy groups such as s-butoxy, i-butoxy, and t-butoxy; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy; C6-10 aryl groups such as phenyl and naphthyl; C6-10 aryl 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, such as 4-methylphenyl, 4-methoxyphenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, and 4-trifluoromethoxyphenyl; and cyano groups.

[0152] "R a1 Specific examples of the "group represented by --CO--" include a formyl group and an acetyl group.

[0153] "R" in Ga b1 In the group represented by -O-CO-, 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. R b1 Specific examples of the substituents in a1 The same examples as those given above can be mentioned.

[0154] "R b1 Specific examples of the "group represented by --O--CO--" include a methoxycarbonyl group, an ethoxycarbonyl group, and a t-butoxycarbonyl group.

[0155] "R" in Ga c1 R d1 In the group represented by N-, 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; R d1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R c1 or R d1 Specific examples of the substituents in a1 The same examples as those given above can be mentioned. where R c1 and R d1 may be taken 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 alkyleneoxyC1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or "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.

[0156] "R c1 R d1 Specific examples of the "group represented by N-" include an amino group, a methylamino group, and a dimethylamino group.

[0157] "R" in Ga c1 R d1 In the group represented by N-CO-, R c1 and R d1 is the above "R c1 R d1 The meanings are the same as those in "a group represented by N-". "R c1 R d1 Specific examples of the "group represented by 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.

[0158] "R" in Ga a1 In the group represented by -CO-O-, R a1 is the above "R a1 The meaning is the same as that of the group represented by -CO-. "R a1 A specific example of the "group represented by --CO--O--" is an acetyloxy group.

[0159] "R" in Ga a1 -CO-NR e1 In the group represented by "-", R a1 is the above "R a1The meaning is the same as that of the group represented by -CO-. R e1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R e1 Specific examples of the substituents in a1 The same examples as those given above can be mentioned. "R a1 -CO-NR e1 Specific examples of the "group represented by -" include an acetylamino group.

[0160] "R" in Ga b1 In the group represented by -O-CO-O-, R b1 is the above "R b1 -O-CO-" has the same meaning as that in "a group represented by -O-CO-". "R b1 Specific examples of the "group represented by --O--CO--O--" include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

[0161] "R" in Ga b1 -O-CO-NR e1 In the group represented by "-", R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "R e1 is the above "R b1 -CO-NR e1 - has the same meaning as that in "a group represented by -". "R b1 -O-CO-NR e1 Specific examples of the "group represented by -" include a methoxycarbonylamino group.

[0162] "R" in Ga c1 R d1 In the group represented by N-CO-O-, R c1 and R d1 is the above "R c1 R d1The meanings are the same as those in "a group represented by N-". "R c1 R d1 Specific examples of the "group represented by N-CO-O-" include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.

[0163] "R" in Ga c1 R d1 N-CO-NR e1 In the group represented by "-", R c1 and R d1 is the above "R c1 R d1 R has the same meaning as in "a group represented by N-" e1 is the above "R a1 -CO-NR e1 - has the same meaning as that in "a group represented by -". "R c1 R d1 N-CO-NR e1 Specific examples of the "group represented by -" include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.

[0164] "R" in Ga b1 SO2-NR e1 In the group represented by "-", R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "R e1 is the above "R a1 -CO-NR e1 - has the same meaning as that in "a group represented by -". "R b1 SO2-NR e1 Specific examples of the "group represented by -" include a methanesulfonylamino group.

[0165] "R" in Ga c1 R d1 In the group represented by N-SO2-, R c1 and R d1 is the above "R c1 R d1The meanings are the same as those in "a group represented by N-". "R c1 R d1 Specific examples of the "group represented by N-SO2-" include an N,N-dimethylaminosulfonyl group.

[0166] "R" in Ga a1 ON=CR f1 In the group represented by "-", R a1 is the above "R a1 The meaning is the same as that of the group represented by -CO-. R f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. R f1 Specific examples of the substituents in a The same examples as those given above can be mentioned. "R a1 ON=CR f1 Specific examples of the "group represented by -" include a (hydroxyimino)methyl group and an (ethoxyimino)methyl group.

[0167] "R" in Ga g1 R h1 In the group represented by C=NO-, 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. R g1 or R h1 Specific examples of the substituents in a1 The same examples as those given above can be mentioned. where R g1 and R h1 may be taken 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 alkyleneoxyC1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on the "C2-5 alkylene group" or "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. "R g1 R h1 Specific examples of the "group represented by C=NO-" include a (propan-2-ylideneamino)oxy group.

[0168] "R" in Ga a1 In the "divalent group represented by -N=", R a1 is the above "R a1 The meaning is the same as that of the group represented by -CO-. "R a1 Specific examples of the "divalent group represented by -N=" include an imino group (HN=) and a methylimino group.

[0169] "R" in Ga a1 In the "divalent group represented by ON=", R a1 is the above "R a1 The meaning is the same as that of the group represented by -CO-. "R a1 Specific examples of the divalent group represented by ON= include an N-hydroxyimino group and an N-methoxyimino group.

[0170] "R" in Ga c1 R d1 In the "divalent group represented by NN=", R c1 and R d1 is the above "R c1 R d1 The meanings are the same as those in "a group represented by N-". "R c1 R d1 A specific example of the divalent group represented by NN= is a 2,2-dimethylhydrazinylidene group.

[0171] "R" in Ga a1 -CO-NR e1 In the "divalent group represented by -N=", R a1 is the above "R a1 -CO- group" has the same meaning as that in "R e1 is the above "R a1 -CO-NR e1 - has the same meaning as that in "a group represented by -".

[0172] "R" in Ga b1 -O-CO-NR e1 In the "divalent group represented by -N=", R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "R e1 is the above "R a1 -CO-NR e1 - has the same meaning as that in "a group represented by -".

[0173] "R" in Ga b1 SO2-NR e1 In the "divalent group represented by -N=", R b1 is the above "R b1 -O-CO- group" has the same meaning as that in "R e1 is the above "R a1 -CO-NR e1 - has the same meaning as that in "a group represented by -".

[0174] 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 alkyleneoxyC1-3 alkylene group" include a dimethyleneoxydimethylene group. Preferred substituents on a "C1-5 alkylene group," "oxyC1-4 alkylene group," "oxyC2-3 alkyleneoxy group," and "C1-3 alkyleneoxyC1-3 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.

[0175] 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, R a1 A group represented by -CO-O-, an oxo group (O=), or R a1 Examples include a divalent group represented by ON=. 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.

[0176] 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, R a1 A group represented by -CO-O-, an oxo group (O=), or R a1 Examples include a divalent group represented by ON=.

[0177] [B] B is an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or -NR N3 -, and 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.

[0178] R N3 The "C1-6 alkyl group" in R may be a straight chain or a branched chain. N3 Examples of the "C1-6 alkyl group" in the above formula 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. R N3 Examples of the "C1-6 alkylcarbonyl group" in the above formula include an acetyl group, a propionyl group, a butyryl group, and an i-propylcarbonyl group.

[0179] R N3In the above, examples of the substituents on the "C1-6 alkyl group" and "C1-6 alkylcarbonyl" 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; (ethoxy) (C1-6 alkylideneamino)oxy groups such as a (C1-6 alkylideneamino)oxy group and a (C1-6 propan-2-ylideneamino)oxy group; a C3-6 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group; a C6-10 aryl group such as a phenyl group or a naphthyl group; a C1-6 alkyl group such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; C6-10 aryl groups substituted with one or more substituents of C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 5-membered heteroaryl groups such as pyrrolyl groups, furyl groups, thienyl groups, imidazolyl groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, and tetrazolyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; Preferred are a 5-membered heteroaryl group substituted with 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, 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.

[0180] [R 7 〕 R 7 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. R 7The "C1-6 alkyl group" in R may be a straight chain or a branched chain. 7 Examples of the "C1-6 alkyl group" in the above formula 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. R 7In the above, examples of the substituent on the "C1-6 alkyl group" 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 hydroxyl groups. (C1-6 alkylideneamino)oxy groups such as (pan-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 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; 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 selected from a 1-6 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, or a C1-6 haloalkoxy group; or a cyano group.

[0181] [Q] Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.

[0182] 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.

[0183] The "5- to 10-membered heterocyclyl group" in Q is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of nitrogen, 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.

[0184] 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; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; 9-membered heteroaryl groups such as indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, and benzisothiazolyl; and 10-membered heteroaryl groups such as quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, and quinoxalinyl. 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.

[0185] 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; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl; C1-6 haloalkyl groups such as butyl groups and 1-fluoro-n-butyl groups; C1-6 alkoxyC1-6 alkyl groups such as methoxymethyl 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; hydroxyC1-6 alkoxy groups such as hydroxyethoxy groups; C1-6 alkoxyalkoxy groups such as methoxymethoxy and methoxyethoxy groups; trimethylsilyloxyethoxy groups, t-butyldimethylsilyl groups tri-C1-6 alkyl-substituted silyloxy-C1-6 alkoxy groups such as silyloxyethoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy groups, 2,3-dichlorobutoxy groups, and trifluoromethoxy groups; C3-6 cycloalkyl-C1-6 alkoxy groups; C6-10 aryl-C1-6 alkoxy groups; (C6-10 aryl 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) C1-6 alkoxy groups; 5 a five-membered heteroaryl C1-6 alkoxy group; a (5-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group) C1-6 alkoxy group; a six-membered heteroaryl C1-6 alkoxy group; a (6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, and a C1-6 haloalkoxy group) C1-6 alkoxy group;C1-6 alkylthio groups such as methylthio group and ethylthio group: C1-6 alkylsulfinyl groups such as methylsulfinyl group and ethylsulfinyl group; C1-6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group: C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; trifluoromethylsulfonyl group, 2,2,2-trifluoroethylthio group C1-6 haloalkylsulfonyl groups such as methylsulfonyl groups; C3-6 cycloalkyl groups such as cyclopropyl groups, cyclobutyl groups, and cyclopentyl groups; C3-6 cycloalkyl groups substituted with one or more substituents 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; 4-methylphenyl groups, 4- a C6-10 aryl 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, such as a methoxyphenyl group, a 4-chlorophenyl group, a 4-fluorophenyl group, a 4-trifluoromethylphenyl group, and a 4-trifluoromethoxyphenyl group; a 3- or 4-membered saturated heterocyclyl group such as an aziridinyl group, an epoxy group, an azetidinyl group, and an oxetanyl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, and 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 C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups; 5-membered heteroaryl groups 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; 6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl groups; and any 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 6-membered heteroaryl group substituted by one or more substituents; 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 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, 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 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; R Q1 A group represented by —CO— (wherein R Q1represents a hydrogen atom; a C1-6 alkyl group; a C1-6 alkyl group substituted by 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 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 alkyl group; (a 5- or 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 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2- and R represents a C6-6 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- or 6-membered heteroaryl group; or a 5- or 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. Q1 The same applies to ); carboxyl group; R Q2 A group represented by —O—CO— (wherein R Q2represents a C1-6 alkyl group; a C1-6 alkyl group substituted by 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 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 alkyl group; (a 5- or 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 alkyl group; a C2-6 alkenyl group; or 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- or 6-membered heteroaryl group; or a 5- or 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. Q2 The same applies to ); R Q1 R Q1 A group represented by N- (R Q1 may be the same or different. Q1 may combine 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— (R in the formula Q1 may be the same or different. Q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R Q1 A group represented by -CO-O-; 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 selected from 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 selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; or a (5- or 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group. Q3 The same applies to ); R Q2 A group represented by -O-CO-O-; R Q2 -O-CO-NR Q3 -; R Q1 R Q1 A group represented by N—CO—O— (R in the formula Q1 may be the same or different. Q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R Q1 R Q1 N-CO-NR Q3 - (wherein R Q1 may be the same or different. Q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. );R Q2 SO2-NR Q3 -; R Q1 R Q1 A group represented by N-SO2- (R in the formula Q1 may be the same or different. Q1may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group; R Q1 -ON=C(R Q4 )- (wherein R Q4 represents a hydrogen atom or a C1-6 alkyl group; (R Q1 )2C=NO- (wherein R Q1 may be the same or different. Q1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a 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.

[0186] 〔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.

[0187] [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.

[0188] [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.

[0189] [ka]

[0190] In formula (II), Y represents an oxygen atom or a sulfur atom; X 1 and X 2 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, 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 C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5-6 membered heterocyclyl group, substituted or unsubstituted 5-6 membered heterocyclyloxy group, nitro group, cyano group, R 1 -CO- group, carboxy group, R 2 a group represented by -O-CO-, R 3 R 4 A group represented by N-, R 3 R 4 A group represented by N—CO—, R 1 a group represented by -CO-O-, R 1 -CO-NR 5 -, a group represented by R 2 a group represented by -O-CO-O-, R 2 -O-CO-NR 5 -, a group represented by R 3 R 4 A group represented by N-CO-O-, R 3 R 4 N-CO-NR5 -, a group represented by R 2 SO2-NR 5 -, a group represented by R 3 R 4 A group represented by N-SO2-, R 1 ON=CR 6 -, a group represented by R 3 R 4 NN=CR 6 -, or R 1 -N=CR 6 - represents a group represented by the formula: R 1 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, R 2 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, R 3 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, R 4 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R 3 and R 4 may be taken together to form a divalent organic group, R 5each independently represents 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; X 3 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, R 1 a group represented by -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, R N1 A group represented by O-, R N1 a group represented by -CO-O-, R N1 a group represented by -O-CO-O-, R N1 R N1 A group represented by N-CO-O-, R N1 a group represented by -CS-O-, R N1 R N1 A group represented by N-CS-O-, R N1 R N2 A group represented by N-, R N1 -CO-NR N2 -, a group represented by R N1 -CO-CO-NR N2 -, a group represented by R N1 -O-CO-NR N2 -, a group represented by R N1 R N1 N-CO-NR N2 -, 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 SO2-NR N2 -, or R N1 -C(=NR N1 )-NR N2 - represents a group represented by R N1 , and R N2 each independently 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 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 5 represents a group represented by HO-A-, a C 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.

[0191] In formula (II), each symbol has the same meaning as in formula (I). X 5 Examples of the "C1-6 alkoxycarbonyl group" in the above formula include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group. X 5 Examples of the "halogeno group" in the above formula include a fluoro group, a chloro group, a bromo group, and an iodo group. The compound of formula (II) includes X 2 But R 1 ON=CR 6 - or a salt thereof.

[0192] [Salts of Production Intermediates and Production Methods] Examples of salts of the production intermediate 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.

[0193] [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.

[0194] The agricultural and horticultural fungicide of the present invention can be used to control plant diseases caused by a wide variety of filamentous fungi, for example, fungi belonging to the phylum Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and Zygomycetes.

[0195] 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 ultimum) etc. Peanut: Brown spot (Mycosphaerella arachidis), soil blotch (Ascochyta sp.), rust (Puccinia arachidis), damping-off (Pythium debaryanum), rust spot (Alternaria alternata), white blight (Sclerotium rolfsii), black spot (Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc. Cucumber: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine wilt (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. Tomatoes: Botrytis cinerea, Cladosporium fulvum, Phytophthora infestans, Verticillium albo-atrum, Verticillium dahliae, Oidium neolycopersici, Alternaria solani, Pseudocercospora fuligena), bacterial wilt (Ralstonia solanacearum), Sclerotinia sclerotiorum, etc. Eggplant: Gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), sooty 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), chlorosis (Fusarium oxysporum), wilt (Verticillium dahliae), sclerotinia sclerotiorum, etc. Onions: Grey rot (Botrytis allii), Grey mould (Botrytis cinerea), White spot leaf blight (Botrytis squamosa), Downy mildew (Peronospora destructor), White blight (Phytophthora porri), Sclerotinia rot (Ciborinia allii), Sclerotinia rot (Botrytis squamosa), Dry rot (Fusarium oxysporum), Red root rot (Pyrenochaeta terrestris), Black rot sclerotinia (Sclerotium cepivorum), Rust (Puccinia allii), Southern blight (Sclerotium rolfsii), etc. Leeks: Soft rot (Pectobacterium carotovorum), Downy mildew (Peronospora destructor), Leaf blight (Pleospora allii), Black rot sclerotinia (Sclerotium cepivorum), Rust (Puccinia allii), White spot leaf blight (Botrytis squamosa), Southern blight (Sclerotium rolfsii), Red root rot (Pyrenochaeta terrestris), etc. Cabbages: Clubroot (Plasmodiophora brassicae), Soft rot (Erwinia carotovora), Black rot (Xanthomonas campesrtis pv. campestris), Black spot bacteria (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), Downy mildew (Peronospora parasitica), Sclerotinia rot (Sclerotinia sclerotiorum), Black smut (Alternaria brassicicola), Grey mould (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, Botrytis cinerea, Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc. Pea: Brown spot (Mycosphaerella blight), gray mold (Botrytis cinerea), sclerotinia sclerotiorum, powdery mildew (Erysiphe pisi), etc.

[0196] 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 disease (Chondrostereum purpureum), crown gall disease (Rhizobium radiobacter, Rhizobium rhizogenes), etc. 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), etc. Persimmon: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora kaki), circular leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), sooty spot (Zygophiala jamaicensis), etc. Peaches: Monilinia fructicola, Monilia fructigena, Cladosporium carpophilum, Phomopsis sp., Xanthomonas campestris pv. pruni, Taphrina deformans, Colletotrichum gloeosporioides, Phloeosporella padi), Kawaratake disease (Coriolus versicolor), etc. Almond: Brown rot (Monilinia laxa), leaf spot (Stigmina carpophila), black spot (Cladosporium carpophilum), leaf blisters (Polystigma rubrum), leaf spot (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc. Prunus: Monilinia fructicola, Colletotrichum acutatum, Alternaria sp., Monilinia kusanoi, Mycosphaerella cerasella, 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 snow disease (causative agent unidentified), crown gall (Rhizobium radiobacter, Rhizobium vitis), etc. Pear: 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), Blister (Pseudomonas syringae), Blast (Exobasidium vexans), etc. Citrus: Common 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: Bacterial blossom rot (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. Olive: Anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), Peacock spot (Spilocaea oleaginea), etc. Chestnut: Anthracnose (Colletotrichum gloeosporioides), etc.

[0197] Wheat: Powdery mildew (Blumeria graminis f.sp. tritici), Scab (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), Brown rust (Puccinia recondita), Yellow rust (Puccinia striiformis), Brown snow blight (Pythium iwayamai), Red snow blight (Monographella nivalis), Eyespot (Pseudocercosporella herpotrichoides), Leaf blotch (Septoria tritici), Glume blotch (Leptosphaeria nodorum), Snow blight (Typhula incarnata), Large sclerotinia snow blight (Myriosclerotinia borealis), Take-all (Gaeumannomyces graminis), Ergot (Claviceps purpurea), Common bunt (Tilletia caries), Loose smut (Ustilago nuda), Blast (Pyricularia grisea), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Barley: Pyrenophora graminea, Pyrenophora teres, Rhynchosporium secalis, Ustilago tritici, U.nuda, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.) etc. Rice: Blast (Pyricularia oryzae), Sheath blight (Rhizoctonia solani), Bakanae disease (Gibberella fujikuroi), Hemerocallis blight (Cochliobolus miyabeanus), Seedling damping-off (Pythium graminicola), Bacterial 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 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. Chrysanthemum: 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 damping-off (Fusarium solani), etc. Gerbera: Gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanthii), etc. Lilies: 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 blight (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 rot (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), verticillium wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), black leg (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), common 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. Corn: 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.

[0198] [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 its salt as an active ingredient. The amount of Compound (I) or its salt contained in the nematicide of the present invention is not particularly limited as long as it exhibits a nematode control effect.

[0199] Specific examples of various plant-parasitic nematodes that can be controlled by the nematicide of the present invention are listed below: (1) Tylenchida (a) From the family Anguinidae, for example, from the genus Anguina, Anguina funesta and Anguina tritici; from the genus Ditylenchus, Ditylenchus destructor, Ditylenchus dipsaci and Ditylenchus myceliophagus; (b) Aphelenchoididae, for example, Aphelenchoides spp., such as the rice root nematode (Aphelenchoides besseyi), the strawberry nematode (Aphelenchoides fragariae), and the peel nematode (Aphelenchoides ritzemabosi); Bursaphelenchus spp., such as the 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) Criconematidae, e.g., Criconema mutabile; (e) Dolichodoridae, e.g., Dolichodorus mediterraneus; (f) Ecphyadophoridae, e.g., Ecphyadophora tenuissima (g) Hemicycliophoridae, e.g., Loofia thienemanni; (h) from the family Heteroderidae, for example, from Globodera species, such as the potato cyst nematode (Globodera rostochiensis), the potato white cyst nematode (Globodera pallida), and the tobacco cyst nematode (Globodera tabacum); from Heterodera species, such as the wheat cyst nematode (Heterodera avenae), the Heterodera cruciferae, the soybean cyst nematode (Heterodera glycines), the sugar beet cyst nematode (Heterodera schachtii), and the 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; others, Rotylenchus robustus, Rotylenchulus reniformis; (j) Meloidogynidae, for example, Meloidogynes pp., Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and Meloidogyne thamesi; (k) of the Nothotylenchidae family, e.g., the strawberry nematode (Nothotylenchus acris); (l) Paratylenchidae, for example, Paratylenchus spp., such as the brown nematode (Paratylenchus curvitatus) and the little nematode (Paratylenchus elachistus); (m) Pratylenchidae, for example, Pratylenchus spp. species, such as Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus, Pratylenchus fallax, Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Pratylenchus scribneri, and Pratylenchus vulnus), corn root-knot nematode (Pratylenchus zeae); others include false root-knot nematode (Nacobbus aberrans), banana root-miner nematode (Radopholus similis), citrus root nematode (Tylenchulus semipenetrans), and citrus root-miner nematode (Radopholus citrophilus).

[0200] (2) Order 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.

[0201] (3) Triplonchida (a) Family Trichodoridae, e.g., Trichodorus primitivus, Paratrichodorus minor.

[0202] [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.

[0203] 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, cuttings, etc. The nematicide can be applied to roots, tubers, tuberous roots, etc. Improved varieties, cultivars, and even mutants, hybrids, and genetically modified organisms (GMOs) of these plants can also be targeted.

[0204] The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc., which are carried out to control various diseases that occur in agricultural and horticultural crops including flowers, turf, and pasture grass. The nematicide can be used for seed treatment, soil application, etc.

[0205] 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 / acaricides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, and animal feed. 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.

[0206] 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:

[0207] Fungicide:

[0208] (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 inhibitors Oxolinic acid.

[0209] (B) Agents acting on the cytoskeleton and motor proteins: B1)~B3) β-tubulin polymerization inhibitors Benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, ethaboxam, chlorfenazole, debacarb, trichlamide, and zarilamid. B4) Cell division inhibitor (unknown site of action) Pencycuron. B5) Spectrin-like protein delocalization inhibitors Fluopicolide, fluopimomide. B6) Actin / myosin / fimbrin function inhibitor Phenamacril, metrafenone, pyriophenone.

[0210] (C) Respiratory agents: C1) Complex I: NADH oxidoreductase inhibitor Diflumetorim, tolfenpyrad, fenazaquin. C2) Complex II: Succinate dehydrogenase inhibitors benodanil, flutolanil, mepronil, isofetamide, fluopyram, cyclobutrifluram, fenfuram, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluindapyr, fluxapyr 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) inhibitor 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 inhibitor 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, triphenyltin chloride, fentin hydroxide. C7) ATP transport inhibitors Silthiofam. C8) Complex III: Cytochrome bc1 (ubiquinone reductase) Qo site, stigmatellin binding subsite inhibitor Ametoctradin.

[0211] (D) Agents acting on amino acid and protein synthesis: D1) Methionine biosynthesis (cgs gene) inhibitor Cyprodinil, mepanipyrim, pyrimethanil. D2) Protein synthesis (ribosome translation termination step) inhibitor Blasticidin S (blasticidin-S). D3), ​​D4) Protein synthesis (ribosomal translation initiation step) inhibitors Kasugamycin, kasugamycin hydrochloride, streptomycin. D5) Protein synthesis (ribosomal polypeptide elongation step) inhibitors Oxytetracycline.

[0212] (E) Signal transduction agents: E1) Signal transduction inhibitors (mechanism of action unknown) Quinoxyfen, proquinazid. E2) MAP / histidine kinase (os-2, HOG1) inhibitors in osmotic signaling Fenpiclonil, fludioxonil. E3) MAP / histidine kinase (os-1, Daf1) inhibitors in osmotic signaling Chlozolinate, dimethachlone, iprodione, procymidone, vinclozolin.

[0213] (F) Agents affecting 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 permeability, fatty acid inhibitor Iodocarb, propamocarb, propamocarb hydrochloride, prothiocarb. F5) Carboxylic Acid Amide (CAA) Fungicides F8) Ergosterol binding inhibitors Natamycin; F9) Lipid homeostasis and transport / storage inhibitors Oxathiapiprolin, fluoxapiprolin.

[0214] (G) Cell membrane sterol biosynthesis inhibitors G1) Inhibitor of C14 demethylase (erg11 / cyp51) in sterol biosynthesis Triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol anol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol iafol, hexaconazole, imibenconazole, ipconazole, mefentrifluconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, fluoxytioconazole, fluconazole, furconazole, fluconazole-cis, diniconazole-M. G2) Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) inhibitors in sterol biosynthesis Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine, buthiobate. G3) 3-ketoreductase (erg27) inhibitors in the C4 demethylation of sterol biosynthesis Fenhexamid, fenpyrazamine. G4) Squalene epoxidase (erg1) inhibitor of sterol biosynthesis Pyributicarb, naftifine, terbinafine.

[0215] (H) Cell wall biosynthesis inhibitors: H4) Chitin synthase inhibitors Polyoxin, polyoxorim. H5) Cellulose synthase inhibitors Dimethomorph, flumorph, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate, mandipropamid.

[0216] (I) Cell wall melanin synthesis inhibitors: I1) Reductase inhibitors of melanin biosynthesis Fthalide, pyroquilon, tricyclazole. I2) Dehydratase inhibitors of melanin biosynthesis Carpropamid, diclocymet, fenoxanil. I3) Polyketide synthase inhibitors for melanin biosynthesis Tolprocarb.

[0217] (P) Agents that induce resistance in host plants: P01-P03) Agents related to salicylic acid signal transduction Acibenzolar-S-methyl, probenazole, tiadinil, isotianil. P04) Polysaccharide elicitor Laminarin. P05) Anthraquinone elicitor Giant knotweed extract (extract from Reynoutria sachalinensis). P06) Microbial elicitors Bacillus mycoides isolate J, cell walls of Saccharomyces cerevisiae strain LAS117. P07) Phosphonate Phosphorous acids and salts such as fosetyl-Al, phosphorous acid and calcium phosphite, aluminum phosphite, sodium phosphite, disodium phosphonate, etc. P08) Agents related to salicylic acid signaling Dichlobentiazox.

[0218] (U) Agents with unknown mechanism of action: Cymoxanil, teclofthalam, triazoxide, flusulfamide, diclomezine, cyflufenamid, dodine, dodine free base, flutianil, ferimzone, tebufloquin, picarbutrazox, validamycin, bethoxazin, cyprofuram, flumetober, nitrothal-isopropyl, propamidine, ipflufenoquin, pyridaclomethicone pyridachlometyl, pyrapropoyne, aminopyrifen, ipfentrifluconazole, quinofumelin, dipymetitrone, chloroinconazide, seboctylamine, flumethylsulfonim, flufenoxadiazam.

[0219] (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 albesilate trialbesilate, anilazine, dithianon, chinomethionat / quinomethionate, fluoroimide, methasulfocarb, dazomet, cufraneb, mancopper, polycarbamate.

[0220] (BM) Biopesticides / Biological Pesticides with Multiple Modes 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, γ-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 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.

[0221] (N) Unclassified agent Mineral oils, organic oils, inorganic salts, material of biological origin, potassium bicarbonate, sodium hydrogen carbonate, calcium carbonate, calcium hydroxide, potassium iodide, potassium phosphonates, chitosan hydrochloride, urea.

[0222] 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:

[0223] 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.

[0224] (1B) Acetylcholinesterase (AChE) inhibitors (organophosphates): 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) salicylatesalicylate, 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.

[0225] (2) GABAergic chloride channel blockers: Chlordane, Endosulfan, Ethiprole, Fipronil, Acetoprole, Camphechlor, Dienochlor, Heptachlor, Pyrafluprole, Pyriprole, Flufiprole.

[0226] (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, β-Cyfluthrin, Cyhalothrin, λ-Cyhalothrin, γ-Cyhalothrin, Cypermethrin, α-Cypermethrin, β-Cypermethrin, theta-Cypermethrin, ζ-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.

[0227] (3B) Sodium channel modulators (DDTs): DDT, Methoxychlor.

[0228] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam, Nicotine, Sulfoxaflor, Flupyradifurone, Triflumezopyrim, Nithiazine, Dichloromezotiaz, Flupyrimin.

[0229] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: Spinetoram, Spinosad.

[0230] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators: Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin, Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.

[0231] (7) Juvenile hormone analogues: Hydroprene, Kinoprene, Methoprene, Fenoxycarb, Pyriproxifen, Diofenolan, Epophenonane, Triprene.

[0232] (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.

[0233] (9) Chordotonal organ TRPV channel modulators: Pymetrozine, Pyrifluquinazon, Afidopyropen.

[0234] (10) Mite growth inhibitors: Clofentezine, Diflovidazin, Hexythiazox, Etoxazole.

[0235] (11) Microbial-derived insect midgut membrane disrupting agents: 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 been engineered with the genes for the toxin proteins (Cry1Ab, etc.) produced by Bt (Bacillus thuringiensis).

[0236] (12) Mitochondrial ATP synthase inhibitors: Diafenthiuron, Azocyclotin, Cyhexatin, Fenbutatin-oxide, Propargite, Tetradifon.

[0237] (13) Oxidative phosphorylation uncouplers that disrupt the proton gradient: Chlorfenapyr, DNOC (4,6-dinitro-o-cresol), Sulfluramid, Binapacryl, Dinobuton, Dinocap.

[0238] (14) Nicotinic acetylcholine receptor (nAChR) channel blockers: Bensultap, Cartap hydrochloride, Thiocyclam, Thiosultap-sodium.

[0239] (15) Chitin biosynthesis inhibitor, type 0: Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron, Fluazuron.

[0240] (16) Chitin biosynthesis inhibitor, type 1: Buprofezin.

[0241] (17) Molting inhibitor: Cyromazine.

[0242] (18) Ecdysone receptor agonists: Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.

[0243] (19) Octopamine receptor agonists: Amitraz, Chlordimeform.

[0244] (20) Mitochondrial electron transport chain complex III inhibitors: Hydramethylnon, Acequinocyl, Fluacrypyrim, Bifenazate.

[0245] (21) Mitochondrial electron transport chain complex I inhibitor (METI): Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad, Rotenone.

[0246] (22) Voltage-dependent sodium channel blockers: Indoxacarb, Metaflumizone.

[0247] (23) Acetyl-CoA carboxylase inhibitors: Spirodiclofen, Spiromesifen, Spirotetramat, Spiropidione.

[0248] (24) Mitochondrial electron transport chain complex IV inhibitors: 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).

[0249] (25) Mitochondrial electron transport chain complex II inhibitors: Cyenopyrafen, Cyflumetofen, Pyflubumide.

[0250] (26) Ryanodine receptor modulators: Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Flubendiamide, Cyhalodiamide, Tetrachlorantraniliprole, Tetraaniliprole.

[0251] (27) Chord tone organ modulator Target region unspecified: Flonicamid.

[0252] (28) GABA-gated chloride channel allosteric modulators: Broflanilide, Fluxametamide, Isocycloseram, Afoxolaner, Fluralaner, Lotilaner, Sarolaner.

[0253] (29) Agents with unknown mechanism of action (UN): Azadirachtin, Benzoximate, Bromopropylate, Chinomethionate / Quinomethionate, Dicofol, Lime sulfur, Mancozeb, Pyridalyl, Sulfur.

[0254] (30) Other insecticides and acaricides: Acynonapyr, Amidoflumet, Benzomate, Benzpyrimoxan, Chlorobenzilate, Dicyclanil, Fenoxacrim, Fentrifanil, Flometoquin, Flubenzimine, Flufenzine, Fluhexafon, Fluopyram, Metaflumizone, Metoxadiazone, Oxazosulfyl, Tetrasul, Triarathene, Tyclopyrazoflor.

[0255] 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 (2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid levulinic acid, daminozide.

[0256] 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: Deworming agent: (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, nitroscanate; (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.

[0257] [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."

[0258] (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 with an active ingredient content of 40%. (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 water was added to the mixture, followed by thorough kneading. The mixture was then 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 is 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 were homogeneously mixed and finely ground, and then an appropriate amount of water was added and the mixture was kneaded to form a clay-like substance. The clay-like substance was granulated and then dried to obtain a water dispersible granule containing 40% of the active ingredient.

[0259] [Antifungal agent 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 and veterinary antifungal agent of the present invention contains at least one selected from compound (I) and its salt as an active ingredient. The amount of compound (I) or its salt contained in the medical antifungal agent of the present invention is not particularly limited as long as it exhibits antifungal effects.

[0260] In this specification, "animal" refers to vertebrates such as pets, livestock, poultry, animals kept on display in zoos and aquariums, captive wild animals, and research and experimental animals.

[0261] 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.

[0262] 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, although 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 the genus Colletotrichium trifolii. Colletotrichium species such as Cryptococcus neoformans; Curvularia species such as Curvularia lunata; Encephalitozoon species such as Encephalitozoon cuniculi; Epicoccum species such as Epicoccum nigrum; Epidermophyton species such as Epidermophyton floccosum; Exophiala species; Exserohilum species such as Exserohilum rostratum; Fusarium species such as Fusarium graminarium, Fusarium solani, and Fusarium sporotrichoides; Fonsecaea species such as Fonsecaea monophora; Histoplasma species such as Histoplasma capsulatum;Leptosphaeria species such as Leptosphaeria nodorum; Malassezia species such as Malassezia globosa; Microsporum species such as Microsporum canis; 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 Rhizoctonia species such as Rhizoctonia solani; Rhizomucor species; Scedosporium species such as Fusarium apiospermum and Scedosporium prolificans; Scopulariopsis species such as Scopulariopsis brevicaulis; Sporothrix species such as Sporothrix schenckii; Talaromyces species such as Talaromyces marneffei; Trichophyton species such as Trichophyton mentagrophytes, Trichophyton interdigitale, Trichophyton rubrum, Trichophyton tonsurans, and Trichophyton verrucosum; Trichophyton species such as Trichosporon asahii and Trichosporon beigelii; and Ustilago species. 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.

[0263] Examples of fungal infections to which the medical and veterinary antifungal agent of the present invention can be applied are shown below, although specific examples are not limited to these.

[0264] The medical and 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 corporis, tinea cruris (jock itch), tinea pedis (athlete's foot), tinea unguium (nail fungus), 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.

[0265] The medical / veterinary antifungal agent of the present invention may contain pharmaceutically acceptable additives. The additives are not particularly limited as long as they are used in known medical drugs. These additives are naturally sterile and non-pyrogenic. Furthermore, additives can be appropriately selected depending on the dosage form and administration method of the antifungal agent.

[0266] 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 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.

[0267] In the case of a solid preparation for oral administration, examples of additives that can be used in the medical and 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, gum arabic, 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 generally used in pharmaceutical preparations. These additives can be incorporated into the medical antifungal agent of the present invention by known methods such as mixing, granulation, tableting, sugar coating, or film coating.

[0268] In the case of a liquid preparation for oral administration, examples of additives that can be used in the medical / veterinary antifungal agent of the present invention include solubilizing agents such as cyclodextrin or modified cyclodextrin, sucrose, glycerin, mannitol, sorbitol, natural gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, and polyvinyl alcohol.

[0269] In the case of a liquid preparation for intramuscular injection, additives that can be used in the medical and veterinary antifungal agent of the present invention include sterilized water, olive oil, ethyl oleate, glycols such as propylene glycol, solubilizers such as cyclodextrin and modified cyclodextrin, etc. Furthermore, an appropriate amount of lidocaine hydrochloride can be added as needed.

[0270] In the case of a liquid preparation for intravenous injection, additives that can be used in the medical and veterinary antifungal agent of the present invention include carriers such as sterile water, solubilizers such as cyclodextrin and modified cyclodextrin, etc. These can also be included in the form of a sterilized isotonic saline solution.

[0271] 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 dosage of the medical and 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, for adults, when administered orally or parenterally (by injection, drip infusion, etc.), the dosage can be 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.

[0272] 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 (Process 1) Synthesis of methyl 3-methoxy-6-((2-methoxyphenyl)ethynyl)pyridazine-4-carboxylate

[0273] [ka]

[0274] Methyl 6-chloro-3-methoxypyridazine-4-carboxylate (2.65 g) was dissolved in dimethylformamide (90 ml) and trimethylamine (150 ml), and 1-ethynyl-2-methoxybenzene (1.90 g), copper(I) iodide (0.42 g), and bis(triphenylphosphine)palladium(II) dichloride (1.34 g) were added to the solution. 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 of the target compound (yield 38%). The obtained target 1 The H-NMR is shown below. 1 H-NMR (400 MHz, CDCl3) 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).

[0275] (Process 2) Synthesis of methyl 3-methoxy-6-(2-methoxyphenethyl)pyridazine-4-carboxylate

[0276] [ka]

[0277] 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.

[0278] (Step 3) Synthesis of 3-methoxy-6-(2-methoxyphenethyl)pyridazine-4-carboxylic acid

[0279] [ka]

[0280] 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.

[0281] (Step 4) Synthesis of N,3-dimethoxy-6-(2-methoxyphenethyl)-N-methylpyridazine-4-carboxamide

[0282] [ka]

[0283] 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 to the solution, followed by stirring at room temperature overnight. Water was poured into the reaction mixture, which was then 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 obtained target 1 The H-NMR is shown below. 1 H-NMR (400 MHz, CDCl3) 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).

[0284] (Step 5) Synthesis of 1-(3-methoxy-6-(2-methoxyphenethyl)-pyridazine-4-yl)ethan-1-one

[0285] [ka]

[0286] 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 saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue (0.19 g) was used directly in the next step.

[0287] (Step 6) Synthesis of 1-(3-methoxy-6-(2-methoxyphenethyl)-pyridazine-4-yl)ethan-1-one O-isopropyl oxime

[0288] [ka]

[0289] 1-(3-Methoxy-6-(2-methoxyphenethyl)pyridazin-4-yl)ethan-1-one (0.19 g) was dissolved in ethanol (4.5 ml) and chloroform (4.5 ml). O-Isopropylhydroxylamine hydrochloride (0.10 g) and pyridine (0.07 ml) were added to the solution, and the mixture was 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 0.25 g of the target product (yield 96%, two steps). The obtained target 1 The H-NMR is shown below. 1H-NMR (400 MHz, CDCl3) 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).

[0290] (Step 7) Synthesis of (E)-4-(1-(isopropoxyimino)ethyl)-6-(2-methoxyphenethyl)-pyridazin-3(2H)-one

[0291] [ka]

[0292] 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.

[0293] (Step 8) Synthesis of (E)-2-(5-(1-(isopropoxyimino)ethyl)-3-(2-methoxyphenethyl)-6-oxopyridazin-1(6H)-yl)-N-isopropylpropanamide

[0294] [ka]

[0295] (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 to the solution, followed by stirring 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 obtained target 1 The H-NMR is shown below. 1 H-NMR (400 MHz, CDCl3) 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).

[0296] 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 (Process 1) Synthesis of 1-(6-chloro-3-methoxypyridazine-4-yl)ethan-1-one O-isopropyl oxime

[0297] [ka]

[0298] 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 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 0.88 g of the target product (yield: 56%). The obtained target 1 The H-NMR is shown below. 1 H-NMR (400 MHz, CDCl3) 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).

[0299] (Process 2) Synthesis of (E)-1-(6-chloro-3-hydroxypyridazin-4-yl)ethan-1-one O-isopropyl oxime

[0300] [ka]

[0301] 1-(6-chloro-3-methoxypyridazin-4-yl)ethan-1-one O-isopropyloxime (0.45 g) was dissolved in N,N-dimethylformamide (8 ml), followed by addition of paratoluenesulfonic acid monohydrate (1.76 g) and lithium chloride (0.39 g), and the mixture was stirred 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.

[0302] (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

[0303] [ka]

[0304] 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 and the mixture was extracted 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 obtained target 1 The H-NMR is shown below. 1 H-NMR (400 MHz, CDCl3) 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).

[0305] (Step 4) Synthesis of (S,E)-2-(2-amino-3-methylbutyl)-6-chloro-4-(1-(isopropoxyimino)ethyl)pyridazin-3(2H)-one hydrochloride salt

[0306] [ka]

[0307] 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). 4 M hydrochloric acid-dioxane solution (6 ml) was slowly added thereto, 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.

[0308] (Step 5) Synthesis of (S,E)-N-(1-(3-chloro-5-(1-(isopropoxyimino)ethyl)-6-oxopyridazin-1(6H)-yl)-3-methylbutan-2-yl)isobutyramide

[0309] [ka]

[0310] The crude product obtained in step 4 was dissolved in dichloromethane (3 ml). Triethylamine (0.25 g) and isobutyryl chloride (0.10 g) were added successively under ice cooling, and the mixture was stirred at room temperature for 30 minutes. Under ice cooling, saturated aqueous sodium bicarbonate was added to the reaction mixture, which was then extracted with dichloromethane. The resulting dichloromethane layer was dried over anhydrous magnesium sulfate and filtered. The 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 obtained target 1 The H-NMR is shown below. 1H-NMR (400 MHz, CDCl3) 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).

[0311] (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

[0312] [ka]

[0313] (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 of the target product (yield 25%). The obtained target 1 The H-NMR is shown below. 1 H-NMR (400 MHz, CDCl3) 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).

[0314] Some of the pyridazinone compounds of the present invention produced by methods similar to those in the above examples are shown in Table 1. In the table, the melting point (° C.) or other physical properties of each compound are also shown.

[0315] [Table 1]

[0316] For some of the compounds in the table, retention times in liquid chromatography mass spectrometry (LCMS) are shown.

[0317] [Table 2]

[0318] The analytical conditions are shown below. A Waters CORTECS UPLC C18 column (Waters, 2.1 x 50 mm, 1.6 μm) was used at 40 °C and a flow rate of 0.6 mL / min, with a 2 μL injection. The mobile phase (A) was water containing 0.1% formic acid, and the mobile phase (B) was acetonitrile. Retention times are reported in minutes. (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 mobile phase (B) was increased from 30% to 95% by weight in a 1.5-minute linear gradient, (II) held at 95% by weight for 0.5 minutes, (III) immediately decreased to 30% by weight (B), and (IV) held at 30% by weight for 0.50 minutes.

[0319] 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 melting point (°C) or other physical properties of each compound are also shown in the table. Some compounds are also shown to be isomer mixtures.

[0320] [Table 3] TIFF0007738656000023.tif217140TIFF0007738656000024.tif217140TIFF0007738656000025.tif174140

[0321] For some of the compounds in the table, retention times in liquid chromatography mass spectrometry (LCMS) are shown. 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 and a flow rate of 0.6 mL / min, with a 2 μL injection, mobile phase (A) water containing 0.1% formic acid, and mobile phase (B) acetonitrile, and retention times were 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) 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 min, then increased from 30% by mass to 95% by mass in a linear gradient of 1.35 min, (II) maintained at 95% by mass for 0.5 min, (III) immediately decreased to 30% by mass (B), and (IV) maintained at 30% by mass for 0.50 min. Method (B): The concentration of the mobile phase (B) was maintained at 30% by mass for 0.15 min, then increased from 30% by mass to 95% by mass in a 0.85 min linear gradient, (II) maintained at 95% by mass for 1.0 min, (III) immediately decreased to 30% by mass (B), and (IV) maintained at 30% by mass for 0.50 min.

[0322] [Table 4]

[0323] 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 melting point (°C) or other physical properties of each compound are also shown in the table. It is also indicated that some compounds are isomer mixtures.

[0324] [Table 5] TIFF0007738656000028.tif196140TIFF0007738656000029.tif196140TIFF0007738656000030.tif196140TIFF00077386560 00031.tif197140TIFF0007738656000032.tif196140TIFF0007738656000033.tif196140TIFF0007738656000034.tif196140

[0325] For some of the compounds in the table, the 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, Waters), and the HPLC / UHPLC detector was a 2998 PDA Photodiode Array Detector (Waters). The column was an XBridgeBEH C18 (Waters, 2.1 x 50 mm, 2.5 μm) and set at 40°C. Water containing 0.1% formic acid was used as mobile phase (A), and acetonitrile was used as mobile phase (B). Mobile phases (A) and (B) were passed through the column at a flow rate of 0.4 mL / min at the following concentrations. The sample was injected in an amount of 6 μL, and the retention time (min) of the sample was measured. 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 rapidly decreased to 30% by mass and maintained at 30% by mass for 2.5 minutes.

[0326] [Table 6]

[0327] Some of the pyridazinone compounds of the present invention prepared by methods similar to those in the above Examples are shown in Table 7. For some of the compounds in the table, their physical properties are also shown. For some compounds, it is also indicated that they are isomer mixtures.

[0328] [Table 7] TIFF0007738656000037.tif196140TIFF0007738656000038.tif196140TIFF0007738656000039.tif196140TIFF0007738656000040.tif147140

[0329] 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.

[0330] [Table 8]

[0331] In addition, some of the compounds that can be used as production intermediates in preparing the pyridazinone compounds of the present invention are shown in Table 9. The table also shows the melting point (° C.) as a physical property of each compound.

[0332] [Table 9]

[0333] [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.

[0334] The control value was calculated according to the following formula.

[0335] [Number 1] Control value (%) = 100 - {lesion area rate in treated area / lesion area rate in untreated area} x 100

[0336] (Test Example 1) Apple scab control test Water was added to emulsion (I) to give a pyridazinone compound concentration of 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 seedlings were inoculated with conidia of the apple scab fungus (Venturia inaequalis) (treated group). As a control, apple seedlings not 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 a 12-hour cycle of light and dark. Two weeks after 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.

[0337] (Test Example 2) Cucumber gray mold control test Water was added to emulsion (I) to make the pyridazinone compound concentration 125 ppm, 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 causal agent of gray mold of cucumber, was dropwise inoculated (treated group). As a control, cucumber seedlings not sprayed with the drug solution were dropwise inoculated in the same manner as above (untreated group). These were then placed 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 ratio, and the control value was calculated. 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.

[0338] (Test Example 3) Wheat powdery mildew control test Water was added to the 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 wheat seedlings (variety "Chihoku," 1-2 leaf stage) grown in seedling pots. After air-drying, the seedlings were inoculated with conidia of wheat powdery mildew (Erysiphe graminis f.sp. tritici) by sprinkling (treated group). As a control, wheat seedlings not sprayed with the drug solution were inoculated in the same manner as above (untreated group). The seedlings 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.

[0339] (Test Example 4) Wheat leaf rust control test Water was added to emulsion (I) to give a pyridazinone compound concentration of 125 ppm, and the compound was dissolved to obtain a drug solution. The drug solution was then sprayed onto wheat seedlings (variety "Norin 61", 1-2 leaf stage) grown in seedling pots. After air-drying, the sprayed wheat seedlings were inoculated with uredospores of wheat leaf rust fungus (Puccinia recondita) by sprinkling them on (treated group). As a control, wheat seedlings not sprayed with the drug solution were inoculated in the same manner as above (untreated group). These were then placed 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 more than 75% control.

[0340] [Antibacterial test] (Test example) Antibacterial test against Fusarium graminearum Fusarium graminearum spores were added and dispersed in glucose-supplemented Minimal SD Base medium, and then a pyridazinone compound dissolved in dimethyl sulfoxide was added to a final concentration of 25 ppm. These were then dispensed into a 96-well microplate and cultured in the dark at 25°C for 3 days. After 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 control. As a result, the following compounds showed excellent growth inhibition rates 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

1. A compound represented by formula (I) or a salt thereof: 【Chemical 1】 [In formula (I), Y represents an oxygen atom or a sulfur atom; X １ represents a hydrogen atom; X ２ is R １ O-N=CR ６ represents a group represented by -; R １ and R 6 each independently represent a substituted or unsubstituted C1-6 alkyl group; X ３ 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, R １ a group represented by —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, R Ｎ１ a group represented by O—, R Ｎ１ a group represented by —CO—O—, R Ｎ１ a group represented by —O—CO—O—, R Ｎ１ R Ｎ１ a group represented by N—CO—O—, R Ｎ１ a group represented by —CS—O—, R Ｎ１ R Ｎ１ a group represented by N—CS—O—, R Ｎ１ R Ｎ２ a group represented by N-, R Ｎ１ -CO-NR Ｎ２ a group represented by -, R Ｎ１ -CO-CO-NR Ｎ２ a group represented by -, R Ｎ１ —O—CO—NR Ｎ２ a group represented by -, R Ｎ１ R Ｎ１ N-CO-NR Ｎ２ 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 R Ｎ１ -C(=NR Ｎ１ )-NR Ｎ２ represents a group represented by -, R Ｎ１ , and R Ｎ２ each independently 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 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-AB-, a group represented by Q-BA-, Q-SO ２ -NR Ｎ３ a group represented by Q-C(R ７ )=N-, a group represented by Q-NR Ｎ３ -SO ２ -, a group represented by Q-N=C(R ７ )- or Q-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; Each B is independently an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or —NR Ｎ３ represents a group represented by -, and 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, R ７ represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.

2. 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.

3. The agricultural and horticultural fungicide according to claim 2, which is used for seed treatment.

4. 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.

5. 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.

6. A compound represented by formula (II) or a salt thereof: 【Chemistry 2】 [In formula (II), Y represents an oxygen atom or a sulfur atom; X １ represents a hydrogen atom; X ２ is R １ O-N=CR ６ represents a group represented by -; R １ and R 6 each independently represent a substituted or unsubstituted C1-6 alkyl group; X ３ 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, R １ a group represented by —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, R Ｎ１ a group represented by O—, R Ｎ１ a group represented by —CO—O—, R Ｎ１ a group represented by —O—CO—O—, R Ｎ１ R Ｎ１ a group represented by N—CO—O—, R Ｎ１ a group represented by —CS—O—, R Ｎ１ R Ｎ１ a group represented by N—CS—O—, R Ｎ１ R Ｎ２ a group represented by N-, R Ｎ１ -CO-NR Ｎ２ a group represented by -, R Ｎ１ -CO-CO-NR Ｎ２ a group represented by -, R Ｎ１ —O—CO—NR Ｎ２ a group represented by -, R Ｎ１ R Ｎ１ N-CO-NR Ｎ２ 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 R Ｎ１ -C(=NR Ｎ１ )-NR Ｎ２ represents a group represented by -, R Ｎ１ , and R Ｎ２ each independently 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 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 ５ 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.

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