2,6-dioxo-3,6-dihydropyrimidine compound

Abstract

To provide a 2,6-dioxo-3,6-dihydropyrimidine compound that has excellent bactericidal activity, has excellent safety, and can be industrially favorably synthesized, and an agricultural and horticultural fungicide, a nematicide, and an antifungal agent for use in medicine / animals that contain the compound as an active ingredient.SOLUTION: A compound represented by Formula (II) or a salt thereof is provided.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to 2,6-dioxo-3,6-dihydropyrimidine compounds and agricultural and horticultural fungicides. More specifically, the present invention relates to 2,6-dioxo-3,6-dihydropyrimidine compounds having excellent bactericidal and antibacterial activities, excellent safety, and being industrially advantageously synthesizable, and agricultural and horticultural fungicides containing the same as an active ingredient. Furthermore, the present invention relates to a nematicide containing the above compound as an active ingredient. Furthermore, the present invention relates to a medical and veterinary antifungal agent containing the above compound as an active ingredient. This application claims priority to Japanese Patent Application No. 2019-195484 filed on October 28, 2019 and Japanese Patent Application No. 2020-053191 filed on March 24, 2020, and incorporates the contents thereof herein by reference.

Background Art

[0002] Various compounds having control activity against crop diseases in the cultivation of agricultural and horticultural crops have been proposed. In order to practically use such compounds as agricultural and horticultural fungicides, it is required not only to have sufficiently high efficacy, but also to be less likely to cause drug resistance, not to cause phytotoxicity to plants or soil pollution, and to have low toxicity to livestock and fish.

[0003] By the way, Patent Document 1 discloses compounds represented by formula (A) and the like.

Chemical Formula

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] An object of the present invention is to provide a 2,6-dioxo-3,6-dihydropyrimidine compound (hereinafter sometimes simply referred to as "dihydropyrimidine compound") that is excellent in bactericidal and antibacterial activities, excellent in safety, and can be synthesized industrially advantageously, and an agricultural and horticultural bactericide containing the same as an active ingredient. Furthermore, it is to provide a nematicide containing the above compound as an active ingredient. Furthermore, it is to provide a medical and veterinary antifungal agent containing the above compound as an active ingredient.

Means for Solving the Problems

[0006] As a result of intensive studies to solve the above problems, the present inventors have completed the present invention including the following aspects.

[0007] 〔1〕A compound represented by formula (II) or a salt thereof.

Chemical formula

Chemical formula

Chemical formula

[10] A compound represented by formula (IV) or a salt thereof. [Chemical formula] [In formula (IV), X 1is 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, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a nitro group, a cyano group, R 1 a group represented by -CO-, a 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 SO 2 -NR 5 a group represented by -, R 3 R 4 N-SO 2 a group represented by -, or R 1 O-N=CR 6 a group represented by -; R1 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 5-6 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 5-6 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 5-6 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, wherein R 3 and R 4 may together form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, R 6 represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 2 is R 1 O-N=CR6 -represented group, R 1 CO-O-N=CR 6 -represented group, R 3 R 4 N-CO-O-N=CR 6 -represented group, R 3 R 4 NR 3 R 4 N-N=CR 6 -represented group, or R 7 -N=CR 6 -represented group; R 1 R 3 R 4 and R 6 are as defined for them in X 1 ; R 7 represents a substituted or unsubstituted 5-membered heterocyclyl group; X 3 represents a substituted or unsubstituted straight-chain C1-6 alkyl group, a substituted or unsubstituted straight-chain C2-6 alkenyl group, a substituted or unsubstituted straight-chain C2-6 alkynyl group, R 1 -CO-represented group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4-6 membered heterocyclyl group; X 4 represents a hydrogen atom or a C1-6 alkoxymethyl group. ]]

Advantages of the Invention

[0008] The dihydropyrimidine compounds of the present invention are excellent in bactericidal and antibacterial activities, have reliable effects, are excellent in safety, and can be synthesized industrially advantageously. The agricultural and horticultural fungicides and nematicides of the present invention have excellent control effects, do not cause phytotoxicity to plants, and have little toxicity to humans, livestock, fish and impact on the environment. The antifungal agents for medical and animal use of the present invention have excellent antibacterial effects and little toxicity to humans, livestock, fish.

Modes for Carrying Out the Invention

[0009] 〔Dihydropyrimidine Compound〕 The dihydropyrimidine compound of the present invention is a compound represented by formula (II) (hereinafter sometimes referred to as compound (II)) or a salt of compound (II).

Chemical formula

[0010]

Chemical formula

[0011] In the present invention, the term "unsubstituted" means that it is only the parent nucleus group. When only the name of the parent nucleus group is described, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom of the parent nucleus group is substituted with a group having the same or different structure as the parent nucleus. Therefore, a "substituent" is another group bonded to the parent nucleus group. The substituent may be one or two or more. Two or more substituents may be the same or different.

[0012] The "substituent" is chemically acceptable and is not particularly limited as long as it has the effects of the present invention. Specific examples of the group that can be a "substituent" include the following groups. 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; C2-6 alkenyl groups such as vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group; C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group;

[0013] C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; C3-6 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group; C6-10 aryl groups such as phenyl group, naphthyl group; C6-10 aryl C1-6 alkyl groups such as benzyl group, phenethyl group; 3-6 membered heterocyclyl groups; 3-6 membered heterocyclyl C1-6 alkyl groups;

[0014] Hydroxyl group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group, propargyloxy group; C6-10 aryloxy groups such as phenoxy group, naphthoxy group; C6-10 aryl C1-6 alkoxy groups such as benzyloxy group and phenethyloxy group;

[0015] Carboxy group; Formyl group; C1-6 alkylcarbonyl groups such as acetyl group and propionyl group; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group and propionyloxy group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;

[0016] C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; C3-6 halocycloalkyl groups such as 3,3-difluorocyclobutyl group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group; C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group and 3-bromobutenyloxy group; C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group and trichloroacetyl group;

[0017] Amino group; C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group and diethylamino group; C6-10 arylamino groups such as anilino group and naphthylamino group; C6-10 aryl C1-6 alkylamino groups such as benzylamino group and phenethylamino group;

[0018] Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino group, propionylamino group, butyrylamino group, and i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, and i-propoxycarbonylamino group; Unsubstituted or substituted aminocarbonyl groups such as carbamoyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, and N-phenyl-N-methylaminocarbonyl group; Imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, and (1-imino)-n-propyl group; Substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as N-hydroxy-iminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N-methoxy-iminomethyl group, and (1-(N-methoxy)-imino)ethyl group; Aminocarbonyloxy group; C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy group and dimethylaminocarbonyloxy group;

[0019] Mercapto group; C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, and t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group; C2-6 alkenylthio groups such as vinylthio group and allylthio group; C2-6 alkynylthio groups such as ethynylthio group and propargylthio group; C1-C6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C1-C6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group; C2-C6 alkenylsulfinyl groups such as allylsulfinyl group; C2-C6 alkynylsulfinyl groups such as propargylsulfinyl group; C1-C6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group; C1-C6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group; C2-C6 alkenylsulfonyl groups such as allylsulfonyl group; C2-C6 alkynylsulfonyl groups such as propargylsulfonyl group; Aminothiocarbonyl group; C1-C6 alkylsulfoximino groups such as S,S-dimethylsulfoximino group;

[0020] Tri-C1-C6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; Tri-C6-C10 aryl-substituted silyl groups such as triphenylsilyl group; Cyano group; Nitro group;

[0021] Terms such as "C1-C6" indicate that the number of carbon atoms in the parent nucleus group is 1 to 6, etc. 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 alkoxy C4 alkyl group because the parent nucleus group is a butyl group and the substituent is an ethoxy group.

[0022] In addition, the above-mentioned "3- to 6-membered heterocyclic group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms as ring-constituting atoms. Examples of the "3- to 6-membered heterocyclic group" include 3- to 6-membered saturated heterocyclic groups, 5- to 6-membered heteroaryl groups, 5- to 6-membered partially unsaturated heterocyclic groups, and the like.

[0023] Examples of the 3- to 6-membered saturated heterocyclic 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, a dioxanyl group, and the like.

[0024] 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, a tetrazolyl group, and the like. Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and the like. Examples of the 5-membered partially unsaturated heterocyclic group include a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group, and the like. Examples of the 6-membered partially unsaturated heterocyclic group include an isoxazolinyl group, a dihydropyranyl group, and the like. Any hydrogen atom in these "substituents" may be substituted with a group having a different structure.

[0025] [Y 1 , Y 2 Y 1 represents an oxygen atom or a sulfur atom, and Y 2 represents an oxygen atom or a sulfur atom. In the present invention, preferred Y 1 ​is an oxygen atom, and preferred Y 2 is an oxygen atom.

[0026] [Z] Z represents a group represented by C-X 1 or a nitrogen atom.

[0027] [X 1 X 1 is 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, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a nitro group, a cyano group, R 1 -CO- group, a carboxy group, R 2 -O-CO- group, R 3 R 4 N- group, R 3 R 4 N-CO- group, R 1 -CO-O- group, R 1 -CO-NR 5 - group, R 2 -O-CO-O- group, R 2 -O-CO-NR 5 - group, R 3 R 4 N-CO-O- group, R 3 R​4 A group represented by N-CO-NR 5 - and R 2 SO 2 -NR 5 - and R 3 R 4 N-SO 2 - or R 1 A group represented by O-N=CR 6 is shown.

[0028] R 1 Each R 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 5-6 membered heterocyclyl group. R 2 Each R 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 5-6 membered heterocyclyl group. R 3 Each R 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 5-6 membered heterocyclyl group. R 4 Each R independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Here, R 3 and R 4 may together form a divalent organic group. R 5 Each R 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 hydrogen atom, a halogeno group, an amino 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 5-6 membered heterocyclyl group.

[0029] X 1 Examples of the "halogeno group" in X include a fluoro group, a chloro group, a bromo group, an iodo group, etc.

[0030] X 1 The "C1-6 alkyl group" in X may be linear or branched. X 1 Examples of the "C1-6 alkyl group" in X 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, an i-hexyl group, etc.

[0031] X 1 Examples of the "C2-6 alkenyl group" in X 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, a 5-hexenyl group, etc.

[0032] X 1Examples of the "C2-6 alkynyl group" in [context] include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, and the like.

[0033] X 1 Examples of the "C1-6 alkoxy group" in [context] include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group, and the like. X 1 Examples of the "C2-6 alkenyloxy group" in [context] include vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group, and the like. X 1 Examples of the "C2-6 alkynyloxy group" in [context] include ethynyloxy group, propargyloxy group, and the like.

[0034] X 1 Examples of the "C1-6 alkylthio group" in [context] include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, and the like. X 1 Examples of the "C1-6 alkylsulfinyl group" in [context] include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group, and the like. X 1 Examples of the "C1-6 alkylsulfonyl group" in [context] include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group, and the like.

[0035] X 1As 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", there are preferably halogeno groups such as fluoro group, chloro group, bromo group, 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, t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy 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; C6-10 aryl groups substituted with any one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group; 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; 5-membered heteroaryl groups substituted with any one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; 6-membered heteroaryl groups substituted with any one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; or cyano group.

[0036] X 1Examples of the "C3-6 cycloalkyl group" in [context] include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. X 1 Examples of the "C3-6 cycloalkyloxy group" in [context] include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and the like.

[0037] X 1 Examples of the "C6-10 aryl group" in [context] include a phenyl group, a naphthyl group, an indanyl group, an indenyl group, a tetralinyl group, and the like. X 1 Examples of the "C6-10 aryloxy group" in [context] include a phenoxy group, a naphthoxy group, and the like.

[0038] X 1 Examples of the "C6-10 arylthio group" in [context] include a phenylthio group, a naphthylthio group, and the like. X 1 Examples of the "C6-10 arylsulfinyl group" in [context] include a phenylsulfinyl group, a naphthylsulfinyl group, and the like. X 1 Examples of the "C6-10 arylsulfonyl group" in [context] include a phenylsulfonyl group, a naphthylsulfonyl group, and the like.

[0039] X 1 The "5-6 membered heterocyclyl group" in [context] is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "5-6 membered heterocyclyl group" include a 5-6 membered saturated heterocyclyl group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heterocyclyl group, and the like.

[0040] Examples of the 5- to 6-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group, and the like. Examples of the 5- to 6-membered heteroaryl group include 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, a tetrazolyl group; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group. Examples of the 5- to 6-membered partially unsaturated heterocyclyl group 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 6-membered partially unsaturated heterocyclyl groups such as an isoxazolinyl group, a dihydropyranyl group.

[0041] X 1 The "5- to 6-membered heterocyclyloxy group" in X has a structure in which a 5- to 6-membered heterocyclyl group is bonded to an oxy group. Specific examples include a thiazolyloxy group, a pyridyloxy group, and the like.

[0042] X 1The substituents on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "5-6 membered heteroaryl group", or "5-6 membered heteroaryloxy group" include halogeno groups such as fluoro group, chloro group, bromo group, 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, n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C6-10 aryl groups such as phenyl group, naphthyl group; C6-10 aryl groups substituted 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 group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group; 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; 5-membered heteroaryl groups 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; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 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 is preferred. Furthermore, as the substituent on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "5-6 membered heterocyclyl group", or "5-6 membered heterocyclyloxy group", an oxo group is also preferred.

[0043] X 1 In the "R 1 -CO- group", 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 5-6 membered heterocyclyl group.

[0044] R 1 Examples of the "C1-6 alkyl group" for R 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, an i-hexyl group, etc. 1 Examples of the "C2-6 alkenyl group" for R include a vinyl group, a 1-propenyl group, etc. 1 Examples of the "C2-6 alkynyl group" for R include an ethynyl group, a 1-propynyl group, etc. 1Examples of the substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" include a halogeno group such as a fluoro group, a chloro group, a bromo group, or an iodo 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 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 C6-10 aryl 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, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group; a 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, or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted with one or more substituents 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 is preferred.

[0045] R 1 Examples of the "C3-6 cycloalkyl group" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. R 1Examples of the "C6-10 aryl group" in [context] include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group, etc.

[0046] R 1 The "5-6 membered heterocyclic group" in [context] is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "5-6 membered heterocyclic group" include a 5-6 membered saturated heterocyclic group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heterocyclic group, etc. Examples of the 5-6 membered saturated heterocyclic group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group, etc. Examples of the 5-6 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, a tetrazolyl group; and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group. Examples of the 5-6 membered partially unsaturated heterocyclic group include 5-membered partially unsaturated heterocyclic groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group; and 6-membered partially unsaturated heterocyclic groups such as an isoxazolinyl group, a dihydropyranyl group.

[0047] R 1As substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5-6 membered heteroaryl group", there are preferably halogeno groups such as fluoro group, chloro group, bromo group, 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, n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C6-10 aryl groups such as phenyl group, naphthyl group; C6-10 aryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group; 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; 5-membered heteroaryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; 6-membered heteroaryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; or cyano group. Furthermore, as substituents on the "C3-6 cycloalkyl group" or "5-6 membered heteroaryl group", an oxo group is also preferred.

[0048] "R 1 Examples of the group represented by "-CO-" include a formyl group, an acetyl group, a propionyl group, a butyryl group, an i-propylcarbonyl group, and the like.

[0049] X 1 In " 2 R 2 In the group represented by "-O-CO-", R R 2 Examples of the substituents in R 1 can be the same as those exemplified in R

[0050] "R 2 Examples of the group represented by "-O-CO-" include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group, and the like.

[0051] X 1 In " 3 R 4 In the group represented by "R 3 R 4 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 5-6 membered heterocyclyl group, and R R 3 Or R 4 Examples of the substituents in R 1 can be the same as those exemplified in R

[0052] Here, R 3 and R 4 may together 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, a tetramethylene group, etc. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group, etc. Examples of the substituent on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a C1-6 alkyl group such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group; or a C1-6 haloalkyl group such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, a 1-fluoro-n-butyl group.

[0053] "R 3 R 4 Examples of the group represented by N- include an amino group, a methylamino group, a dimethylamino group, an i-propylamino group, etc.

[0054] X 1 In "R 3 R 4 the group represented by N-CO-, R 3 and R 4 have the same meaning as those in the above "R 3 R 4 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, an N-(i-propyl)-N-methylaminocarbonyl group, and the like.

[0055] X 1 In "R 1 -CO-O-", R 1 has the same meaning as that in the above "R 1 -CO-". "R 1 -CO-O-" Specific examples of the group represented by include an acetyloxy group, an i-propylcarbonyloxy group, and the like.

[0056] X 1 In "R 1 -CO-NR 5 -", R 1 has the same meaning as that in the above "R 1 -CO-". R 5 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R 5 Specific examples of the substituents in are the same as those exemplified in R 1 . "R 1 -CO-NR 5 -" Specific examples of the group represented by include an acetylamino group, an i-propylcarbonylamino group, and the like.

[0057] X 1 In "R 2 -O-CO-O-", R 2 has the same meaning as that in the above "R 2 -O-CO-". "R 2Specific examples of the group represented by "-O-CO-O-" include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, and the like.

[0058] X 1 In "R 2 -O-CO-NR 5 - represented by", R 2 has the same meaning as that in the above-mentioned group represented by "R 2 -O-CO-". R 5 has the same meaning as that in the above-mentioned group represented by "R 1 -CO-NR 5 - represented by". "R 2 -O-CO-NR 5 - represented by" include a methoxycarbonylamino group and the like.

[0059] X 1 In "R 3 R 4 N-CO-O- represented by", R 3 and R 4 have the same meaning as those in the above-mentioned group represented by "R 3 R 4 N- represented by". "R 3 R 4 N-CO-O- represented by" include a carbamoyloxy group, an N,N-dimethylaminocarbonyloxy group, and the like.

[0060] X 1 In "R 3 R 4 N-CO-NR 5 - represented by", R 3 and R 4 have the same meaning as those in the above-mentioned group represented by "R 3 R 4 N- represented by". R 5 has the same meaning as that in the above-mentioned group represented by "R 1 -CO-NR 5 - represented by". "R3 R 4 N-CO-NR 5 Specific examples of the group represented by "-" include a carbamoyl amino group, an N,N-dimethylaminocarbonyl amino group, and the like.

[0061] X 1 In "R 2 SO 2 -NR 5 -", in the group represented by "R 2 is the same as that in the group represented by "-O-CO-". R 2 is the same as that in the group represented by "-CO-NR 5 -". 1 -CO-NR 5 -". "R 2 SO 2 -NR 5 -", specific examples of the group represented by "-" include a methanesulfonyl amino group and the like.

[0062] X 1 In "R 3 R 4 N-SO 2 -", in the group represented by "R 3 and R 4 are the same as those in the group represented by "R 3 R 4 N-". "R 3 R 4 N-SO 2 -", specific examples of the group represented by "-" include an N,N-dimethylaminosulfonyl group and the like.

[0063] X 1 In "R 1 O-N=CR 6 -", in the group represented by "R 1 is the same as that in the group represented by "-CO-". 1 -". R 6represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 6 Specific examples of the "substituted or unsubstituted C1-6 alkyl group" or "substituted or unsubstituted 5-6 membered heterocyclyl group" in R 1 can be the same as those exemplified in R R 6 Examples of the "halogeno group" in R R 6 include a fluoro group, a chloro group, a bromo group, an iodo group, etc. Examples of the "mono C1-6 alkylamino group" in the "substituted or unsubstituted mono C1-6 alkylamino group" in R R 6 include a methylamino group, an ethylamino group, an i-propylamino group, etc. Examples of the "di C1-6 alkylamino group" in the "substituted or unsubstituted di C1-6 alkylamino group" in R R 6 include a dimethylamino group, a diethylamino group, an N-methyl-N-i-propylamino group, etc. Examples of the "C1-6 alkoxy group" in the "substituted or unsubstituted C1-6 alkoxy group" in R R 6 include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, an i-hexyloxy group, etc. Examples of the "C1-6 alkylthio group" in the "substituted or unsubstituted C1-6 alkylthio group" in R R 6Examples of the substituents on the "C1-6 alkoxy group", "mono-C1-6 alkylamino group", "di-C1-6 alkylamino group", or "C1-6 alkylthio group" in [compound name] are R 1 which are the same as those exemplified as the substituents on the "C1-6 alkyl group" in [compound name]. "R 1 O-N=CR 6 -represented group" specific examples include (hydroxyimino)methyl group, (ethoxyimino)methyl group, 1-(i-propoxyimino)ethyl group, etc.

[0064] In the present invention, preferred X 1 includes a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. More preferably, X 1 is a hydrogen atom.

[0065] 〔X 2 〕 X 2 is a group represented by R 1 O-N=CR 6 -, a group represented by R 1 CO-O-N=CR 6 -, a group represented by R 3 R 4 N-CO-O-N=CR 6 -, a group represented by R 3 R 4 N-N=CR 6 -, or a group represented by R 7 -N=CR 6 -. Also, R 1 , R 3 , R 4 , and R 6 have the same meaning as those in X 1 . R 7 represents a substituted or unsubstituted 5-membered heterocyclyl group. Specific examples of the substituents in X 2 are the same as those exemplified in X 1 . R 7The "5-membered heterocyclic group" herein contains 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring-constituting atoms. Examples of the "5-membered heterocyclic group" include a 5-membered saturated heterocyclic group, a 5-membered heteroaryl group, a 5-membered partially unsaturated heterocyclic group and the like. Examples of the 5-membered saturated heterocyclic group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a dioxolanyl group and the like. 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, a tetrazolyl group and the like. Examples of the 5-membered partially unsaturated heterocyclic group include a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group and the like.

[0066] R 7Examples of the substituent on the "5-membered heterocyclic group" 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; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, and 1-fluoro-n-butyl 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; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; C6-10 aryl groups substituted with one or more substituents selected from halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups, such as 4-chlorophenyl group, 4-trifluoromethylphenyl group, and 4-trifluoromethoxyphenyl group; 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, and tetrazolyl group; 5-membered heteroaryl groups substituted with one or more substituents selected from C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, and triazinyl group; 6-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, or C1-6 haloalkoxy groups; or cyano group is preferred.

[0067] In the present invention, preferred X 2 Examples of R 1 include a group represented by O-N=CR 6 -. R 1Examples thereof include a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group. R 6 Examples thereof include a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. “R 1 O-N=CR 6 Examples of the group represented by “-” include a (hydroxyimino)methyl group, an (ethoxyimino)methyl group, a 1-(ethoxyimino)ethyl group, a 1-(i-propoxyimino)ethyl group, and the like.

[0068] 〔Q〕 Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-10 membered heterocyclyl group.

[0069] Examples of the “C6-10 aryl group” in Q include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group, and the like.

[0070] The “5-10 membered heterocyclyl group” in Q is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. It may be either a monocyclic or polycyclic group. Examples of the “5-10 membered heterocyclyl group” include a 5-6 membered saturated heterocyclyl group, a 5-10 membered heteroaryl group, a 5-10 membered partially unsaturated heterocyclyl group, and the like.

[0071] Examples of the saturated heterocyclic group having 5 to 6 members include pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like. Examples of the heteroaryl group having 5 to 10 members include 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; 9-membered heteroaryl groups such as indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, benzimidazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, benzoisothiazolyl group; 10-membered heteroaryl groups such as quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group. Examples of the partially unsaturated heterocyclic group having 5 to 10 members include 5-membered partially unsaturated heterocyclic groups such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group; 6-membered partially unsaturated heterocyclic groups such as isoxazolinyl group, dihydropyranyl group; 9-membered partially unsaturated heterocyclic groups such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group; 10-membered partially unsaturated heterocyclic groups such as 1,2,3,4-tetrahydroquinolinyl group.

[0072] Examples of the substituent on the "C6-10 aryl group" or "5-10 membered hetero-cyclic group" in Q include halogeno groups such as fluoro group, chloro group, bromo group, 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, n-hexyl group; C2-6 alkenyl groups such as vinyl group; C2-6 alkynyl groups such as ethynyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; C1-6 alkoxy C1-6 alkyl groups such as methoxymethyl group; hydroxyl group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; hydroxy C1-6 alkoxy groups such as hydroxyethoxy group; C1-6 alkoxyalkoxy groups such as methoxymethoxy group, methoxyethoxy group; tri C1-6 alkyl substituted silyloxy C1-6 alkoxy groups such as trimethylsilyloxyethoxy group, t-butyldimethylsilyloxyethoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl C1-6 alkoxy groups; C6-10 aryl C1-6 alkoxy groups; (C6-10 aryl) C1-6 alkoxy groups substituted with any one or more substituents selected from C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 5-membered heteroaryl C1-6 alkoxy groups; (5-membered heteroaryl) C1-6 alkoxy groups substituted with any one or more substituents selected from C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups; 6-membered heteroaryl C1-6 alkoxy groups; (6-membered heteroaryl) C1-6 alkoxy groups substituted with any one or more substituents selected from C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups;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; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group and cyclopentyl group; C3-6 cycloalkyl 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, a C1-6 haloalkoxy group, or a cyano group; C3-6 cycloalkenyl groups such as cyclopropenyl group, cyclobutenyl group and cyclopentenyl group; C6-10 aryl groups such as phenyl group and naphthyl group; C6-10 aryl 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, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group; 3- to 4-membered saturated heterocyclyl groups such as aziridinyl group, epoxy group, azetidinyl group and oxetanyl group; 3- to 4-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, or a C1-6 haloalkoxy group; 5- to 6-membered saturated heterocyclyl groups such as pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group and dioxanyl group; 5- to 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, or a C1-6 haloalkoxy group;A 5-membered heteroaryl group such as a pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; 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, or a C1-6 haloalkoxy group; A 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 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; A 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group; A 5-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; A 6-membered partially unsaturated heterocyclyl group such as an isoxazolinyl group, dihydropyranyl group; A 6-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; R Q1 A group represented by -CO- (wherein R Q1is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a C1-6 alkyl group substituted with one or more substituents of a 5-6 membered heteroaryl 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 substituted with one or more substituents of a C6-10 aryl)C1-6 alkyl 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 substituted with one or more substituents of a 5-6 membered heteroaryl)C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with 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 5-6 membered heteroaryl group; or a 5-6 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; as shown below for R Q1 is the same in the following R carboxy group; R Q2 -O-CO- group (wherein R Q2is a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a C1-6 alkyl group substituted with one or more substituents of a 5-6 membered heteroaryl 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 substituted with one or more substituents of a C6-10 aryl)C1-6 alkyl 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 substituted with one or more substituents of a 5-6 membered heteroaryl)C1-6 alkyl group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 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; as shown below for R Q2 is the same in the following R R Q1 R Q1 a group represented by N- (wherein R Q1 may be the same or different. R 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- (wherein R Q1 may be the same or different. R 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 A group represented by - (wherein R Q3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a C1-6 alkyl group substituted with one or more substituents of a 5-6 membered heteroaryl group; a (C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C6-10 aryl) C1-6 alkyl group; or a (C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) 5-6 membered heteroaryl) C1-6 alkyl group; The same applies to R Q3 below. ); R Q2 A group represented by -O-CO-O-; R Q2 -O-CO-NR Q3 A group represented by -; R Q1 R Q1 A group represented by N-CO-O- (wherein R Q1 may be the same or different. R Q1 may combine with each other 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-NR Q3 - (wherein R Q1 may be the same or different. R q1 may combine with each other to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. ); R Q2 SO 2 -NR Q3 A group represented by -; R Q1 R Q1 N-SO 2 A group represented by - (wherein R Q1 may be the same or different. R Q1They may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.); R Q1 -O-N=C(R Q4 )-represents a group (wherein R Q4 represents a hydrogen atom or a C1-6 alkyl group.);(R Q1 ) 2 A group represented by C=N-O-(wherein R Q1 may be the same or different. R Q1 They may combine 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 heterocyclic group", an oxo group is also preferred.

[0073] [X 3 X 3 represents a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, a group represented by R 1 -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 heterocyclic group.

[0074] X 3 Examples of the "linear C1-6 alkyl group" in X X 3 Examples of the "linear C2-6 alkenyl group" in X X 3 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 "linear C2-6 alkynyl group" in X include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, and the like. X 3 Examples of the "4-membered heterocyclic group" in X include azetidinyl group and oxetanyl group. X 3 Specific examples of the other substituents in X 1 can be the same as those exemplified in X.

[0075] In the present invention, preferred X 3 includes a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted C6-10 aryl group.

[0076] Examples of the substituent on the linear C1-6 alkyl group, the substituent on the linear C2-6 alkenyl group, the substituent on the linear C2-6 alkynyl group, the substituent on the C3-6 cycloalkyl group, the substituent on the C6-10 aryl group, or the substituent on the 4-6 membered heterocyclic group include one or more substituents selected from the following substituent groups (hereinafter, this substituent may be represented by the symbol "G"). Further, when there are two or more substituents (G), two of them may combine to form a divalent organic group. The following shows the substituent groups. A halogen group, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C2-C6 alkenyl group, a substituted or unsubstituted C2-C6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-C6 alkoxy group, a substituted or unsubstituted C2-C6 alkenyloxy group, a substituted or unsubstituted C2-C6 alkynyloxy group, a substituted or unsubstituted C1-C6 alkylthio group, a substituted or unsubstituted C1-C6 alkylsulfinyl group, a substituted or unsubstituted C1-C6 alkylsulfonyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C3-C6 cycloalkyloxy group, a substituted or unsubstituted C6-C10 aryl group, a substituted or unsubstituted C6-C10 aryloxy group, a substituted or unsubstituted C6-C10 arylthio group, a substituted or unsubstituted C6-C10 arylsulfinyl group, a substituted or unsubstituted C6-C10 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 A group represented by -CO-, a 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 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 Rd N-CO-NR e -represented group, R c R d N-CO-CO-NR e -represented group, R a -CS-NR e -represented group, R c R d N-CS-NR e -represented group, R b SO 2 -NR e -represented group, R c R d N-SO 2 -represented group, R a O-N=CR f -represented group, R h R j C=N-O-represented group, R a -C(=NR g )-NR e -represented group, R c R d N-C(=NR g )-represented group, R h R i S(=O)=N-CO-represented group, R h R i S=N-CO-represented group.

[0077] Among the above-mentioned substituent groups, 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 5-6 membered heterocyclyl group. R cEach 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 5-6 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 together form a divalent organic group. R e Each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group. R f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group. R g Each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R h Each independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R i Each independently represents a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, where R h and R i may together form a divalent organic group.

[0078] Examples of the "halogeno group" in G include a fluoro group, a chloro group, a bromo group, an iodo group, etc.

[0079] The "C1-6 alkyl group" in G may be linear or branched. Examples of the "C1-6 alkyl group" in 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, an i-hexyl group, and the like.

[0080] Examples of the "C2-6 alkenyl group" in 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, a 5-hexenyl group, and the like.

[0081] Examples of the "C2-6 alkynyl group" in 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, a 1,1-dimethyl-2-butynyl group, and the like.

[0082] 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, a t-butoxy group, an i-hexyloxy group, and the like. Examples of the "C2-6 alkenyloxy group" in G include a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group, and the like. Examples of the "C2-6 alkynyloxy group" in G include an ethynyloxy group, a propargyloxy group, and the like.

[0083] 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, an i-propylthio group, and the like. Examples of the "C1-6 alkylsulfinyl group" in G include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like. Examples of the "C1-6 alkylsulfonyl group" in G include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.

[0084] As the substituent 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, a halogeno group such as a fluoro group, a chloro group, a bromo group, or an iodo 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 C1-6 alkylthio group such as a methylthio group or an ethylthio group; a C1-6 alkylsulfinyl group such as a methylsulfinyl group or an ethylsulfinyl group; a C1-6 alkylsulfonyl group such as a methylsulfonyl group or an ethylsulfonyl 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 C6-10 aryl 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, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; a 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, or a tetrazolyl group; a 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, or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, or a triazinyl group; a 6-membered heteroaryl group substituted with one or more substituents 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 is preferred.

[0085] Examples of the "C3-6 cycloalkyl group" in G include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. Examples of the "C3-6 cycloalkyloxy group" in G include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, etc.

[0086] Examples of the "C6-10 aryl group" in G include a phenyl group, a naphthyl group, etc. Examples of the "C6-10 aryloxy group" in G include a phenoxy group, a naphthoxy group, etc.

[0087] Examples of the "C6-10 arylthio group" in G include a phenylthio group, a naphthylthio group, etc. Examples of the "C6-10 arylsulfinyl group" in G include a phenylsulfinyl group, a naphthylsulfinyl group, etc. Examples of the "C6-10 arylsulfonyl group" in G include a phenylsulfonyl group, a naphthylsulfonyl group, etc.

[0088] The "3-10 membered heterocyclyl group" in G is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. It may be either a monocyclic or a polycyclic group. Examples of the "3-10 membered heterocyclyl group" include a 3-6 membered saturated heterocyclyl group, a 5-10 membered heteroaryl group, a 5-10 membered partially unsaturated heterocyclyl group, etc.

[0089] Examples of the saturated heterocyclic group having 3 to 6 members include aziridinyl group, epoxy group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like. Examples of the heteroaryl group having 5 to 10 members include 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; 9-membered heteroaryl groups such as indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, benzimidazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, benzoisothiazolyl group; 10-membered heteroaryl groups such as quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group; Examples of the partially unsaturated heterocyclic group having 5 to 10 members include 5-membered partially unsaturated heterocyclic groups such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group; 6-membered partially unsaturated heterocyclic groups such as isoxazolinyl group, dihydropyranyl group; 9-membered partially unsaturated heterocyclic groups such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group; 10-membered partially unsaturated heterocyclic groups such as 1,2,3,4-tetrahydroquinolinyl group;

[0090] The "heterocyclic oxy group having 3 to 10 members" in G has a structure in which a heterocyclic group having 3 to 10 members is bonded to an oxy group. Specific examples include thiazolyloxy group, pyridyloxy group and the like.

[0091] As 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, there are halogeno groups such as fluoro group, chloro group, bromo group, 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, n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10 aryl C1-6 alkoxy group; (C6-10 aryl) C1-6 alkoxy group substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 5-membered heteroaryl C1-6 alkoxy group; (5-membered heteroaryl) C1-6 alkoxy group substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 6-membered heteroaryl C1-6 alkoxy group; (6-membered heteroaryl) C1-6 alkoxy group substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; C1-6 alkylthio groups such as methylthio group, ethylthio group; C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group; C1-6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group;C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group: C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group; C3-6 cycloalkyl 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, a C1-6 haloalkoxy group, or a cyano group; C3-6 cycloalkenyl group; C6-10 aryl groups such as phenyl group, naphthyl group; C6-10 aryl 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, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group; 3-4 membered saturated heterocyclyl groups such as aziridinyl group, epoxy group, azetidinyl group, oxetanyl group; 3-4 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, or a C1-6 haloalkoxy group; 5-6 membered saturated heterocyclyl groups such as pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group; 5-6 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, or a C1-6 haloalkoxy group; 5 membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group;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, or a C1-6 haloalkoxy group; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, 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; a 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group; a 5-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered partially unsaturated heterocyclyl group such as an isoxazolinyl group, a dihydropyranyl group; a 6-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; R G1 -CO- (wherein R G1is 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 5-6 membered heteroaryl group; a (C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a (5-6 membered heteroaryl)C1-6 alkyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 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; as shown below for R G1 is the same in the following); a carboxy group; R G2 a group represented by -O-CO- (wherein R G2is 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 5-6 membered heteroaryl group; a (C6-10 aryl) C1-6 alkyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a (5-6 membered heteroaryl) C1-6 alkyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a cyano group; a C6-10 aryl group; a C6-10 aryl group substituted with one or more substituents 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 5-6 membered heteroaryl group; or a 5-6 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; as shown below for R G2 is the same in the following.); R G1 R G1 a group represented by N- (wherein R q1 may be the same or different. R G1 may combine with each other to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.); R G1 R G1 a group represented by N-CO- (wherein R G1 may be the same or different. R G1 may combine with each other 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 A group represented by - (wherein R G3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a C1-6 alkyl group substituted with one or more substituents of a 5-6 membered heteroaryl group; a (C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C6-10 aryl)C1-6 alkyl group substituted with one or more substituents of any one of; or a (C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) 5-6 membered heteroaryl)C1-6 alkyl group substituted with one or more substituents of any one of; is shown. The same applies to R G3 below.); R G2 A group represented by -O-CO-O-; R G2 -O-CO-NR G3 A group represented by -; R G1 R G1 A group represented by N-CO-O- (wherein R G1 may be the same or different. R 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-NR G3 - (wherein R G1 may be the same or different. R G1 may combine together to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.); R G2 SO 2 -NR G3 A group represented by -; R G1 R G1 N-SO 2 A group represented by - (wherein R G1 may be the same or different. R G1They may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.); R G1 -O-N=C(R G4 )-represents a group (wherein R G4 represents a hydrogen atom or a C1-6 alkyl group.);(R G1 ) 2 A group represented by C=N-O-(wherein R G1 may be the same or different. R G1 They may combine 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", "C3-6 cycloalkyloxy group", "3-10 membered heterocyclyl group", or "3-10 membered heterocyclyloxy group", an oxo group is also preferred.

[0092] In the group represented by "R a -CO-" in G, R a represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3-10 membered heterocyclyl group.

[0093] R a Examples of the "C1-6 alkyl group" in R R a Examples of the "C2-6 alkenyl group" in R R aExamples of the "C2-6 alkynyl group" in [description] include an ethynyl group, a 1-propynyl group, and the like. R aExamples of the substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" 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; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy 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; carboxy group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, and t-butoxycarbonyl group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group; C6-10 aryl groups such as phenyl group and naphthyl group; C6-10 aryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, and 4-trifluoromethoxyphenyl group; 5-membered heteroaryl groups such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, and tetrazolyl group; 5-membered heteroaryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, and triazinyl group; 6-membered heteroaryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group;A cyano group is preferred.;

[0094] R a Examples of the "C3-6 cycloalkyl group" in R include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. R a Examples of the "C6-10 aryl group" in R include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group, etc.

[0095] R a The "3- to 10-membered heterocyclyl group" in R is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. It may be either a monocyclic or polycyclic group. Examples of the "3- to 10-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, etc. 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, a dioxanyl group, etc. Examples of the 5- to 10-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; 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group; 9-membered heteroaryl groups such as an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a benzothiazolyl group, and a benzoisothiazolyl group; 10-membered heteroaryl groups such as a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group. Examples of the 5- to 10-membered partially unsaturated heterocyclic group include 5-membered partially unsaturated heterocyclic groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, and an oxazolinyl group; 6-membered partially unsaturated heterocyclic groups such as an isoxazolinyl group and a dihydropyranyl group; 9-membered partially unsaturated heterocyclic groups such as an indolinyl group, an isoindolinyl group, a 2,3-dihydrobenzofuranyl group, and a 1,3-dihydrobenzofuranyl group; 10-membered partially unsaturated heterocyclic groups such as a 1,2,3,4-tetrahydroquinolinyl group.

[0096] R aExamples of the substituent on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "3-10 membered heteroaryl group" 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; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, and 1-fluoro-n-butyl 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; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10 aryl C1-6 alkoxy group; (C6-10 aryl) C1-6 alkoxy group substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 5-membered heteroaryl C1-6 alkoxy group; (5-membered heteroaryl) C1-6 alkoxy group substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 6-membered heteroaryl C1-6 alkoxy group; (6-membered heteroaryl) C1-6 alkoxy group substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 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;A C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group or a 2,2,2-trifluoroethylsulfonyl group; a C3-6 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group or a cyclopentyl group; a C3-6 cycloalkyl 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, a C1-6 haloalkoxy group, or a cyano group; a C3-6 cycloalkenyl group; a C6-10 aryl group such as a phenyl group or a naphthyl group; a C6-10 aryl 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, such as a 4-methylphenyl group, a 4-methoxyphenyl group, a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, or a 4-trifluoromethoxyphenyl group; a 3-4 membered ring saturated heterocyclyl group such as an aziridinyl group, an epoxy group, an azetidinyl group or an oxetanyl group; a 3-4 membered ring saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered ring 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 5-6 membered ring saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered ring heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group or a tetrazolyl group; a 5-membered ring 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; a 6-membered ring 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; a 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group; a 5-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 6-membered partially unsaturated heterocyclyl group such as an isoxazolinyl group, a dihydropyranyl group; a 6-membered partially saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; R q1 -CO- group (wherein R q1is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a C1-6 alkyl group substituted with one or more substituents of a 5-6 membered heteroaryl group; a (C6-10 aryl)C1-6 alkyl group substituted with one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a (5-6 membered heteroaryl)C1-6 alkyl group substituted with one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, 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 any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-6 membered heteroaryl group; or a 5-6 membered heteroaryl group substituted with one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; as shown below for R q1 is the same in the following R carboxy group; R q2 -O-CO- group (wherein R q2is a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a C1-6 alkyl group substituted with one or more substituents of a 5-6 membered heteroaryl group; a (C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C6-10 aryl C1-6 alkyl group substituted with one or more substituents of any one of them; a (C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) 5-6 membered heteroaryl C1-6 alkyl group substituted with one or more substituents of any one of them; a C2-6 alkenyl group; a C2-6 haloalkenyl group; a C2-6 alkynyl group; a C2-6 haloalkynyl group; a C3-6 cycloalkyl group; a C3-6 cycloalkyl group substituted with 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 5-6 membered heteroaryl group; or a 5-6 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; as shown below for R q2 is the same in); R q1 R q1 a group represented by N- (wherein R q1 may be the same or different. R q1 may combine with each other to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.); R q1 R q1 a group represented by N-CO- (wherein R q1 may be the same or different. R q1They may combine 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 A group represented by - (wherein R q3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a C1-6 alkyl group substituted with one or more substituents of a 5-6 membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a (5-6 membered heteroaryl)C1-6 alkyl group substituted with one or more substituents of any one of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; The same applies to R q3 hereinafter.); R q2 A group represented by -O-CO-O-; R q2 -O-CO-NR q3 A group represented by -; R q1 R q1 A group represented by N-CO-O- (wherein R q1 may be the same or different. R q1 They may combine 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-NR q3 - (wherein R q1 may be the same or different. R q1 They may combine to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.); R q2 SO 2 -NR q3 A group represented by -; R q1 R q1 N-SO2 -represents a group (wherein R q1 may be the same or different. R q1 groups may combine with each other to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.); R q1 -O-N=C(R q4 )-represents a group (wherein R q4 represents a hydrogen atom or a C1-6 alkyl group.); (R q1 ) 2 a group represented by C=N-O- (wherein R q1 may be the same or different. R q1 groups may combine with each other 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 "3-10 membered heteroaryl group", an oxo group is also preferred.

[0097] Specific examples of the group represented by "R a -CO-" include a formyl group, an acetyl group, an i-propylcarbonyl group, and the like.

[0098] In "R b -O-CO-" in G, R b represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heteroaryl group. R b Specific examples of the substituents in R a can be the same as those exemplified in R

[0099] "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, a t-butoxycarbonyl group, and the like.

[0100] "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 5-6 membered heterocyclyl group, and R d represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group. R c or R d Specific examples of the substituents in are the same as those exemplified in R a can be listed. R d Examples of the "C1-6 alkoxy group" in R include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, an s-butoxy group, a t-butoxy group, an i-hexyloxy group, and the like. R dExamples of the substituent on the "C1-6 alkoxy group" 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; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group; C6-10 aryl groups such as phenyl group and naphthyl group; C6-10 aryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, and 4-trifluoromethoxyphenyl group; or cyano group are preferred.

[0101] Here, R c and R d may together form a divalent organic group. Examples of the divalent organic group that can be formed include substituted or unsubstituted C2-5 alkylene group, substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group, substituted or unsubstituted C1-3 alkylenethio C1-3 alkylene group, or substituted or unsubstituted C1-3 alkyleneimino C1-3 alkylene group. Furthermore, silicon-containing divalent hydrocarbon groups such as -CH 2 CH 2 -Si(CH 3 ) 2 -CH 2 CH 2 - can be mentioned. Examples of the "C2-5 alkylene group" include dimethylene group, trimethylene group, and tetramethylene group. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include dimethyleneoxydimethylene group. Examples of the "C1-3 alkylene thio C1-3 alkylene group" include a dimethylene thio dimethylene group. Examples of the "C1-3 alkylene imino C1-3 alkylene group" include a dimethylene imino dimethylene 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 alkylene oxy C1-3 alkylene group", "C1-3 alkylene thio C1-3 alkylene group" and "C1-3 alkylene imino C1-3 alkylene group" include halogeno groups such as fluoro group, chloro group, bromo group, 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; methylidene group; or C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group.

[0102] 「R c R d Specific examples of the group represented by "N-" include amino group, methylamino group, dimethylamino group, i-propylamino group and the like.

[0103] In G, "R c R d In the group represented by "N-CO-", R c and R d have the same meanings as those in the above "R c R d group represented by "N-". 「R c R d Specific examples of the group represented by "N-CO-" include carbamoyl group, N,N-dimethylaminocarbonyl group, N-(i-propyl)aminocarbonyl group, N-(i-propyl)-N-methylaminocarbonyl group and the like.

[0104] In G, "R c Rd N-NR d "In the group represented by -CO-, R" c "and R" d "have the same meaning as those in the above-mentioned ""group represented by R" c "R" d "N-." "R" c "R" d "N-NR" d "Specific examples of the group represented by -CO- include a 2,2-dimethylhydrazine-1-carbonyl group and the like."

[0105] "In the group represented by R" a "-CO-O- in G, R" a "has the same meaning as that in the above-mentioned ""group represented by R" a "-CO-." "R" a "Specific examples of the group represented by -CO-O- include an acetyloxy group and the like."

[0106] "In the group represented by R" a "-CO-NR" e "- in G, R" a "has the same meaning as that in the above-mentioned ""group represented by R" a "-CO-." "R" e "represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group." "R" e "Specific examples of the substituents in are the same as those exemplified in R" a "." "R" a "-CO-NR" e "- Specific examples of the group represented by include an acetylamino group, a propionylamino group, a butyrylamino group, an i-propylcarbonylamino group, and the like."

[0107] "In the group represented by R" a "-CO-CO-NR" e "- in G, R"a represents the same meaning as that in the above-mentioned "group represented by R a -CO-". R e represents the same meaning as that in the above-mentioned "group represented by R a -CO-NR e -". "Examples of the "group represented by R a -CO-CO-NR e -" include an oxopropanamide group and the like.

[0108] In G, for the "group represented by R a -CO-NR e -NR e -", R a represents the same meaning as that in the above-mentioned "group represented by R a -CO-". R e represents the same meaning as that in the above-mentioned "group represented by R a -CO-NR e -". "Examples of the "group represented by R a -CO-NR e -NR e -" include an acetylhydrazinyl group, an i-propylcarbonylhydrazinyl group, and the like.

[0109] In G, for the "group represented by R a -CO-NR e -NR e -CO-", R a represents the same meaning as that in the above-mentioned "group represented by R a -CO-". R e represents the same meaning as that in the above-mentioned "group represented by R a -CO-NR e -". "Examples of the "group represented by R a -CO-NR e -NR e -CO-" include a 2-acetylhydrazine-1-carbonyl group and the like.

[0110] In G, for the "Rb In the group represented by "-O-CO-O-", R b has the same meaning as that in the above-mentioned "R b -O-CO- group". "R b -O-CO-O- group", specific examples thereof include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, and the like.

[0111] In G, in the group represented by "R b -O-CO-NR e -", R b has the same meaning as that in the above-mentioned "R b -O-CO- group". R e has the same meaning as that in the above-mentioned "R b -CO-NR e - group". "R b -O-CO-NR e - group", specific examples thereof include a methoxycarbonylamino group, and the like.

[0112] In G, in the group represented by "R c R d N-CO-O-", R c and R d have the same meanings as those in the above-mentioned "R c R d N- group". "R c R d N-CO-O- group", specific examples thereof include a carbamoyloxy group, an N,N-dimethylaminocarbonyloxy group, and the like.

[0113] In G, in the group represented by "R c R d N-CO-NR e -", R c and R d have the same meanings as those in the above-mentioned "R c R d N- group". R eis the same as that in the above-mentioned "R a -CO-NR e -represented group". "R c R d N-CO-NR e -represented group" can include, for example, a carbamoylamino group, an N,N-dimethylaminocarbonylamino group, etc.

[0114] In "R c R d N-CO-CO-NR e -represented group" in G, R c and R d have the same meaning as those in the above-mentioned "R c R d N-represented group". R e has the same meaning as that in the above-mentioned "R a -CO-NR e -represented group". "R c R d N-CO-CO-NR e -represented group" can include, for example, a 2-(methylamino)-2-oxoacetamide group, a 2-(t-butylamino)-2-oxoacetamide group, etc.

[0115] In "R a -CS-NR e -represented group" in G, R a has the same meaning as that in the above-mentioned "R a -CO-represented group". R e has the same meaning as that in the above-mentioned "R a -CO-NR e -represented group". "R a -CS-NR e -represented group" can include, for example, an ethanethioamide group, a propanethioamide group, a 2-methylpropanethioamide group, etc.

[0116] In "R c Rd N-CS-NR e -represented group」, R c and R d have the same meaning as those in the above-mentioned 「R c R d -represented by N-group」. R e has the same meaning as that in the above-mentioned 「R a -CO-NR e -represented group」. 「R c R d N-CS-NR e -represented group」, specific examples include 3,3-dimethylthioureido group and the like.

[0117] In G, 「R b SO 2 -NR e -represented group」, R b has the same meaning as that in the above-mentioned 「R b -represented by -O-CO-group」. R e has the same meaning as that in the above-mentioned 「R a -CO-NR e -represented group」. 「R b SO 2 -NR e -represented group」, specific examples include methanesulfonylamino group and the like.

[0118] In G, 「R c R d N-SO 2 -represented group」, R c and R d have the same meaning as those in the above-mentioned 「R c R d -represented by N-group」. 「R c R d N-SO 2 -represented group」, specific examples include N,N-dimethylaminosulfonyl group and the like.

[0119] In G, 「Ra O-N=CR f -represented group", R a is the same as that in the above "R a -CO-represented group". 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 R a can be the same as those exemplified in R "R a O-N=CR f -represented group" include, for example, (hydroxyimino)methyl group, (ethoxyimino)methyl group, etc.

[0120] In "R a -C(=NR g )-NR e -represented group" in G, R a is the same as that in the above "R a -CO-represented group". R e is the same as that in the above "R a -CO-NR e -represented 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 g Specific examples of the substituents in R a can be the same as those exemplified in R

[0121] In "R c R d N-C(=NR g )-represented group" in G, R c and R d are the same as those in the above "R c R d N-represented group". R g is the same as the above "R a -C(=NRg )-NR e represents the same meaning as that in the group represented by "-".

[0122] In G, "R 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, and 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 R a can be the same as those exemplified in R

[0123] Here, R h and R i may together 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, a tetramethylene group, etc. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group, etc. Examples of the substituents on the "C2-5 alkylene group" or the "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as a fluoro group, a chloro group, a bromo group, an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group; or 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.

[0124] In G, "Rh R i In the group "a group represented by S = N-CO-", R h or R i has the same meaning as those in the above "R h R i a group represented by S(=O)=N-CO-".

[0125] In "R h R j a group represented by C = N-O-", in G, R h and R j has the same meaning as that in the above "R h R j a group represented by S = N-O-". "R h R j Specific examples of the group represented by C = N-O-" include a (propan-2-ylideneamino)oxy group and the like.

[0126] When there are two or more substituents (G), examples of the divalent organic group that can be formed by two of them together include a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxy C1-4 alkylene group, a substituted or unsubstituted oxy C2-3 alkyleneoxy group, or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group. Examples of the "C1-5 alkylene group" include a methylene group, a dimethylene group, a trimethylene group, a tetramethylene group, and the like. Examples of the "oxy C1-4 alkylene group" include an oxymethylene group, an oxydimethylene group, and the like. Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethyleneoxy group, and the like. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group, and the like. As substituents on “C1-5 alkylene group”, “oxy C1-4 alkylene group”, “oxy C2-3 alkyleneoxy group”, “C1-3 alkyleneoxy C1-3 alkylene group”, halogeno groups such as fluoro group, chloro group, bromo group, 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; or C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group are preferred.

[0127] In the present invention, preferred Gs include halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 3-10 membered heterocyclyl group, R b a group represented by -O-CO-, R c R d a group represented by R-N-, R c R d a group represented by R-N-CO-, R a a group represented by -CO-O-, R a -CO-NR e a group represented by R-N-CO-NR b -O-CO-NR e a group represented by R-N-CO-O-, R c R d a group represented by R-N-CO-NR c R d N-CS-NR e a group represented by R-N-CS-NR c R d N-CS-NR e a group represented by R-N-CS-NR b SO 2 -NR e a group represented by R-N-SO-R a O-N=CR f a group represented by R-N-O-N=CR or R h R iExamples of the group represented by C=N-O- can be mentioned.

[0128] 〔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, or a substituted or unsubstituted C3-6 cycloalkylene group.

[0129] Examples of the "C1-6 alkylene group" in A include a methylene group, a dimethylene group, a trimethylene group, a tetramethylene group, etc. 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-CH 2 -, -CH 2 -CH=CH-), etc. Examples of the "C2-6 alkynylene group" in A include an ethynylene group (-C≡C-), a propynylene group (-CH 2 -C≡C-, -C≡C-CH 2 -), etc. Examples of the "C3-6 cycloalkylene group" in A include a 1,2-cyclopropylene group, a 1,2-cyclobutanediyl group, a 1,3-cyclobutanediyl group, etc.

[0130] In the present invention, preferred examples of A include a substituted or unsubstituted C1-6 alkylene group or a substituted or unsubstituted C2-6 alkenylene group. Examples of the substituent on the C1-6 alkylene group or C2-6 alkenylene group include one or more substituents selected from the following substituent groups (hereinafter, this substituent may be represented by the symbol "Ga"). Also, when there are two or more substituents (Ga), two of them may combine to form a divalent organic group. The following shows the substituent groups. A halogen 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 C3-6 cycloalkyl group, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 3-6 membered heterocyclyl group, a substituted or unsubstituted 3-6 membered heterocyclyloxy group, a nitro group, a cyano group, R a1 A group represented by -CO-, a 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 SO 2 -NR e1 A group represented by -, R c1 R d1 N-SO 2 A group represented by -, R a1 O-N=CR f1 A group represented by -, R g1 R h1A group represented by C=N-O-, an oxo group (O=), a thioxo group (S=), R a1 A divalent group represented by -N=, R a1 A divalent group represented by O-N=, R c1 R d1 A divalent group represented by N-N=, 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 SO 2 -NR e1 A divalent group represented by -N=.

[0131] Among the above substituent groups, R a1 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 5-6 membered heterocyclyl group, R b1 each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group, R c1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 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 together 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 5-6 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 together form a divalent organic group.

[0132] Examples of the "halogeno group" in Ga include a fluoro group, a chloro group, a bromo group, an iodo group, etc.

[0133] 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, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group, etc.

[0134] Examples of the "C2-6 alkenyl group" in 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, a 5-hexenyl group, etc.

[0135] Examples of the "C2-6 alkynyl group" in Ga include an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, and the like.

[0136] Examples of the "C1-6 alkoxy group" in Ga include a methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group, and the like. Examples of the "C2-6 alkenyloxy group" in Ga include a vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group, and the like. Examples of the "C2-6 alkynyloxy group" in Ga include an ethynyloxy group, propargyloxy group, and the like.

[0137] Examples of the "C1-6 alkylthio group" in Ga include a methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, and the like. Examples of the "C1-6 alkylsulfinyl group" in Ga include a methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group, and the like. Examples of the "C1-6 alkylsulfonyl group" in Ga include a methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group, and the like.

[0138] As 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, there are halogeno groups such as fluoro group, chloro group, bromo group, 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, t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy 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; C6-10 aryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group; or cyano group are preferred.

[0139] Examples of the "C3-6 cycloalkyl group" in Ga include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like. Examples of the "C3-6 cycloalkyloxy group" in Ga include cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group and the like.

[0140] Examples of the "C6-10 aryl group" in Ga include phenyl group, naphthyl group, indenyl group, indanyl group, tetralinyl group and the like. Examples of the "C6-10 aryloxy group" in Ga include phenoxy group, naphthoxy group and the like.

[0141] Examples of the "C6-10 arylthio group" in Ga include a phenylthio group, a naphthylthio group, and the like. Examples of the "C6-10 arylsulfinyl group" in Ga include a phenylsulfinyl group, a naphthylsulfinyl group, and the like. Examples of the "C6-10 arylsulfonyl group" in Ga include a phenylsulfonyl group, a naphthylsulfonyl group, and the like.

[0142] The "3-6 membered ring heterocyclyl group" in Ga is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "3-6 membered ring heterocyclyl group" include a 3-6 membered ring saturated heterocyclyl group, a 5-6 membered ring heteroaryl group, a 5-6 membered ring partially unsaturated heterocyclyl group, and the like.

[0143] Examples of the 3-6 membered ring 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, a dioxanyl group, and the like. Examples of the 5-6 membered ring heteroaryl group include 5-membered ring 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, a tetrazolyl group; and 6-membered ring heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group. Examples of the 5-6 membered ring partially unsaturated heterocyclyl group include 5-membered ring partially unsaturated heterocyclyl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group; and 6-membered ring partially unsaturated heterocyclyl groups such as an isoxazolinyl group, a dihydropyranyl group.

[0144] In Ga, the "3- to 6-membered heterocyclyloxy group" has a structure in which a 3- to 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group, a pyridyloxy group, and the like.

[0145] As substituents on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "3- to 6-membered heterocyclyl group", or "3- to 6-membered heterocyclyloxy group" in Ga, there are halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group, an n-pentyl group, and an n-hexyl group; C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, and a 1-fluoro-n-butyl group; a hydroxyl group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, an s-butoxy group, an i-butoxy group, and a t-butoxy group; C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, and a trifluoromethoxy group; C6-10 aryl groups such as a phenyl group and a naphthyl group; C6-10 aryl 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, 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 is preferred.

[0146] In Ga, "R a1 -CO- group", R a1represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group.

[0147] R a1 Examples of the "C1-6 alkyl group" in 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, an i-hexyl group, and the like. R a1 Examples of the "C2-6 alkenyl group" in include a vinyl group, a 1-propenyl group, and the like. R a1 Examples of the "C2-6 alkynyl group" in include an ethynyl group, a 1-propynyl group, and the like. R a1 Examples of the substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in include a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo 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, a t-butoxy group; a C1-6 haloalkoxy group such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, a trifluoromethoxy group; a C3-6 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group; a C6-10 aryl group such as a phenyl group, a naphthyl group; a C6-10 aryl group substituted with one or more substituents selected from a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group such as a 4-chlorophenyl group, a 4-trifluoromethylphenyl group, a 4-trifluoromethoxyphenyl group; or a cyano group.

[0148] R a1Examples of the "C3-6 cycloalkyl group" in include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like. R a1 Examples of the "C6-10 aryl group" in include a phenyl group, a naphthyl group, and the like.

[0149] R a1 The "5-6 membered heteroaryl group" in is a group containing 1, 2, 3, or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring-constituting atoms. When there are two or more heteroatoms, they may be the same or different. Examples of the "5-6 membered heteroaryl group" include a 5-6 membered saturated heteroaryl group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heteroaryl group, and the like. Examples of the 5-6 membered saturated heteroaryl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group, and the like. Examples of the 5-6 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, a tetrazolyl group; 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group. Examples of the 5-6 membered partially unsaturated heteroaryl group include 5-membered partially unsaturated heteroaryl groups such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group, an oxazolinyl group; 6-membered partially unsaturated heteroaryl groups such as an isoxazolinyl group, a dihydropyranyl group.

[0150] R a1Examples of the substituent on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5-6 membered heteroaryl group" in [Compound Name] 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; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, and 1-fluoro-n-butyl 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; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; C6-10 aryl groups substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group, such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, and 4-trifluoromethoxyphenyl group; or cyano group are preferred.

[0151] "R a1 Examples of the group represented by -CO- include formyl group and acetyl group.

[0152] In [Compound Name], in the group represented by "R b1 -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 5-6 membered heteroaryl group. R b1 Specific examples of the substituent in R a1 can be the same as those exemplified in R

[0153] 「R b1 -O-CO- represented group」 specific examples include methoxycarbonyl group, ethoxycarbonyl group, t-butoxycarbonyl group and the like.

[0154] In Ga, for the group represented by 「R c1 R d1 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 5-6 membered heterocyclyl group, and R d1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. R c1 Or R d1 Specific examples of the substituents in are the same as those exemplified in R a1 can be mentioned. Here, R c1 and R d1 may together 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, a tetramethylene group and the like. Examples of the 「C1-3 alkyleneoxy C1-3 alkylene group」 include a dimethyleneoxydimethylene group and the like. Examples of substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro 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, and t-butyl group; or C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, and 1-fluoro-n-butyl group.

[0155] "R c1 R d1 Examples of the group represented by N- include amino group, methylamino group, dimethylamino group, and the like.

[0156] In Ga, in the group represented by "R c1 R d1 N-CO-", R c1 and R d1 have the same meaning as those in the above "R c1 R d1 group represented by N-". "R c1 R d1 Examples of the group represented by N-CO- include carbamoyl group, N,N-dimethylaminocarbonyl group, N-(i-propyl)aminocarbonyl group, N-(i-propyl)-N-methylaminocarbonyl group, and the like.

[0157] In Ga, in the group represented by "R a1 -CO-O-", R a1 has the same meaning as that in the above "R a1 group represented by -CO-". "R a1 Examples of the group represented by -CO-O- include acetyloxy group and the like.

[0158] In Ga, in the group represented by "R a1 -CO-NR e1 -", R a1 has the same meaning as that in the above "R a1It shows the same meaning as that in 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 can be the same as those exemplified in "R a1 -CO-NR e1 -represented groups" can include, for example, an acetylamino group.

[0159] In Ga, in the group represented by "R b1 -O-CO-O-", R b1 has the same meaning as that in the group represented by the above "R b1 -O-CO-". "R b1 -O-CO-O-represented groups" can include, for example, a methoxycarbonyloxy group, an ethoxycarbonyloxy group, etc.

[0160] In Ga, in the group represented by "R b1 -O-CO-NR e1 -", R b1 has the same meaning as that in the group represented by the above "R b1 -O-CO-". R e1 has the same meaning as that in the group represented by the above "R b1 -CO-NR e1 -". "R b1 -O-CO-NR e1 -represented groups" can include, for example, a methoxycarbonylamino group, etc.

[0161] In Ga, in the group represented by "R c1 R d1 N-CO-O-", R c1 and R d1 have the same meaning as that in the above "R c1 R d1It shows the same meaning as those in the group represented by "N-". "R c1 R d1 Specific examples of the group represented by "N-CO-O-" include a carbamoyloxy group, an N,N-dimethylaminocarbonyloxy group, and the like.

[0162] In Ga, "R c1 R d1 N-CO-NR e1 -", in the group represented by R c1 and R d1 have the same meaning as those in the above-mentioned "R c1 R d1 N-". R e1 has the same meaning as that in the above-mentioned "R a1 -CO-NR e1 -". "R c1 R d1 N-CO-NR e1 -", specific examples of the group represented by include a carbamoylamino group, an N,N-dimethylaminocarbonylamino group, and the like.

[0163] In Ga, "R b1 SO 2 -NR e1 -", in the group represented by R b1 has the same meaning as that in the above-mentioned "R b1 -O-CO-". R e1 has the same meaning as that in the above-mentioned "R a1 -CO-NR e1 -". "R b1 SO 2 -NR e1 -", specific examples of the group represented by include a methanesulfonylamino group, and the like.

[0164] In Ga, "R c1 R d1 N-SO 2 -", in the group represented by R c1 and R d1represents the same meaning as those in the above-mentioned "group represented by R c1 R d1 N-". "R c1 R d1 N-SO 2 -". Specific examples of the "group represented by" include N,N-dimethylaminosulfonyl group and the like.

[0165] In Ga, in the "group represented by R a1 O-N=CR f1 -", R a1 represents the same meaning as that in the above-mentioned "group represented by R a1 -CO-". R f1 represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group. R f1 Specific examples of the substituents in are the same as those exemplified in R a . "R a1 O-N=CR f1 -". Specific examples of the "group represented by" include (hydroxyimino)methyl group, (ethoxyimino)methyl group and the like.

[0166] In Ga, in the "group represented by R g1 R h1 C=N-O-", 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 5-6 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 are the same as those exemplified in R a1 . Here, R g1 and R h1may combine to form a divalent organic group together. Examples of the divalent organic group that can be formed include a substituted or unsubstituted C2-5 alkylene group or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group. Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group, etc. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group, etc. Examples of the substituent on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as a fluoro group, a chloro group, a bromo group, an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, a t-butyl group; or 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, etc. are preferred. "R g1 R h1 Examples of the group represented by C=N-O- include a (propan-2-ylideneamino)oxy group, etc.

[0167] In Ga, in the "divalent group represented by R a1 -N=", R a1 has the same meaning as that in the above "group represented by R a1 -CO-". "R a1 Examples of the divalent group represented by -N= include an imino group (HN=), a methylimino group, etc.

[0168] In Ga, in the "divalent group represented by R a1 O-N=", R a1 has the same meaning as that in the above "group represented by R a1 -CO-". "R a1Specific examples of the divalent group represented by "O-N=" include an N-hydroxyimino group, an N-methoxyimino group, and the like.

[0169] In Ga, "R c1 R d1 In the divalent group represented by "N-N=", R c1 and R d1 have the same meaning as those in the above "R c1 R d1 group represented by "N-". "R c1 R d1 Specific examples of the divalent group represented by "N-N=" include a 2,2-dimethylhydrazinylidene group and the like.

[0170] In Ga, "R a1 -CO-NR e1 -N=" in the divalent group represented by, R a1 has the same meaning as that in the above "R a1 group represented by "-CO-". R e1 has the same meaning as that in the above "R a1 -CO-NR e1 - group represented by.

[0171] In Ga, "R b1 -O-CO-NR e1 -N=" in the divalent group represented by, R b1 has the same meaning as that in the above "R b1 group represented by "-O-CO-". R e1 has the same meaning as that in the above "R a1 -CO-NR e1 - group represented by.

[0172] In Ga, "R b1 SO 2 -NR e1 -N=" in the divalent group represented by, R b1 has the same meaning as that in the above "R b1 group represented by "-O-CO-". R e1 has the same meaning as that in the above "R a1-CO-NR e1 It shows the same meaning as that in the group represented by "-".

[0173] 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 oxy C1-4 alkylene group, a substituted or unsubstituted oxy C2-3 alkyleneoxy group, or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group. Examples of the "C1-5 alkylene group" include a methylene group, a dimethylene group, a trimethylene group, a tetramethylene group, etc. Examples of the "oxy C1-4 alkylene group" include an oxymethylene group, an oxydimethylene group, etc. Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethyleneoxy group, etc. Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group, etc. Examples of the substituents on the "C1-5 alkylene group", "oxy C1-4 alkylene group", "oxy C2-3 alkyleneoxy group", and "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group, an i-butyl group, and a t-butyl group; or C1-6 haloalkyl groups such as a chloromethyl group, a chloroethyl group, a trifluoromethyl group, a 1,2-dichloro-n-propyl group, and a 1-fluoro-n-butyl group are preferred.

[0174] In the present invention, preferred Ga includes a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, Ra1 -CO-O-, an oxo group (O=), or R a1 Examples thereof include a divalent group represented by O-N=. In this case, examples of the preferable substituted or unsubstituted 5- to 6-membered heterocyclyloxy group include a tetrahydro-2H-pyran-4-yl group.

[0175] In the present invention, more preferable G includes a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, R a1 -CO-O-, an oxo group (O=), or R a1 Examples thereof include a divalent group represented by O-N=.

[0176] [Salt] The salt of compound (II) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; salts of organic bases such as triethylamine, tributylamine, pyridine, and hydrazine; ammonia, etc. can be mentioned.

[0177] [Production method] The production method of compound (II) or the salt of compound (II) is not limited. For example, compound (II) or the salt of compound (II) of the present invention can be obtained by a known method as described in the examples, etc. Also, the salt of compound (II) can be obtained from compound (II) by a known method.

[0178] (Reaction Scheme 1) For example, among compounds (II), the compound of formula (I-1) shown below can be prepared by condensing the compound of formula (III-1) and the compound of formula (A) as shown in the following Reaction Scheme 1.

[0179] [ka]

[0180] In formula (I-1), X 1# represents X in formula (II). 1 or by common practice, X 1 The structure that can be derived to X 2# represents X in formula (II). 2 or by common practice, X 2 The structure that can be derived to X 3# represents X in formula (II). 3 or by common practice, X 3 The structure that can be derived from Q # represents the same meaning as Q in formula (II) or a structure which can be derived to Q by a general method. # has the same meaning as A in formula (II) or represents a structure which can be derived to A by a general method. The symbols in formula (III-1) have the same meanings as those in formula (I-1). X in formula (A) 3# has the same meaning as in formula (I-1). L represents a leaving group. For example, when a compound of formula (A) having a leaving group such as a methanesulfonyloxy group in L is used, the compound can be prepared by reacting in the presence of an inorganic base. For example, when a compound of formula (A) in which L is a hydroxyl group is used, it can be prepared by using the Mitsunobu reaction.

[0181] (Reaction Scheme 2) Compounds of formula (III-1) can be prepared by condensing compounds of formula (B) and formula (C), as shown in Reaction Scheme 2 below.

[0182] [ka]

[0183] The symbols in formula (B) have the same meanings as those in formula (I-1). The symbols in formula (C) have the same meanings as those in formula (I-1). Hal represents a halogeno group. For example, it can be prepared by reacting a compound of formula (B) with a compound of formula (C) in the presence of an inorganic base.

[0184] (Reaction Scheme 3) Among the compounds of formula (B), the compound of formula (B-1) in which the X 2 moiety is a group represented by R 1 O-N=CR 6 - can be prepared by condensing a compound of formula (D) with a compound of formula (E) as shown in the following Reaction Scheme 3.

[0185] [Chemical formula]

[0186] R in formula (B-1) 1 and R 6 have the same meanings as those in formula (II). X 1# has the same meaning as that in formula (I-1). R in formula (D) 6 has the same meaning as that in formula (II). X 1# has the same meaning as that in formula (I-1). R in formula (E) 1 has the same meaning as that in formula (II). Note that the hydrochloride salt of the compound of formula (E) may be used. For example, it can be prepared by reacting a compound of formula (D) with a compound of formula (E) in an alcohol solvent.

[0187] (Reaction Scheme 4) Among the compounds of formula (I-1), the compound of formula (I-2) in which the X 2 moiety is a group represented by R 1 O-N=CR 6 - can be prepared by condensing a compound of formula (F) with a compound of formula (E) as shown in the following Reaction Scheme 4.

[0188] [Chemistry]

[0189] R in formula (I-2) 1 and R 6 have the same meaning as that in formula (II). Other symbols have the same meaning as those in formula (I-1). R in formula (F) 6 has the same meaning as that in formula (II). Other symbols have the same meaning as those in formula (I-1). R in formula (E) 1 has the same meaning as that in formula (II). For the compound of formula (E), its hydrochloride salt may be used. For example, it can be prepared by reacting the compound of formula (D) with the compound of formula (E) in an alcohol solvent.

[0190] (Reaction Scheme 5) The compound of formula (I-1) can also be prepared by condensing the compound of formula (IV-1) with the compound of formula (C) as shown in the following Reaction Scheme 5.

[0191] [Chemistry]

[0192] The symbols in formula (IV-1) have the same meaning as those in formula (I-1). The symbols in formula (C) have the same meaning as those in formula (I-1). Hal represents a halogen group. For example, it can be prepared by reacting the compound of formula (IV-1) with the compound of formula (C) in the presence of an inorganic base.

[0193] [Production Intermediate] The compound represented by the following formula (III) or its salt can be used as a production intermediate in the production of the compound represented by formula (II).

[0194] [Chemistry]

[0195] In formula (III), X 1 is 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, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a nitro group, a cyano group, R 1 -CO- group, a carboxy group, R 2 -O-CO- group, R 3 R 4 N- group, R 3 R 4 N-CO- group, R 1 -CO-O- group, R 1 -CO-NR 5 - group, R 2 -O-CO-O- group, R 2 -O-CO-NR 5 - group, R 3 R 4 N-CO-O- group, R 3 R 4 N-CO-NR 5 - group, R 2 SO 2 -NR 5 - group, R 3 R4 N-SO 2 -represented group, or R 1 O-N=CR 6 -represented group; R 1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C2-C6 alkenyl group, a substituted or unsubstituted C2-C6 alkynyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C6-C10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group, R 2 each independently represents a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C2-C6 alkenyl group, a substituted or unsubstituted C2-C6 alkynyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C6-C10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group, R 3 each independently represents a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C2-C6 alkenyl group, a substituted or unsubstituted C2-C6 alkynyl group, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C6-C10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group, R 4 each independently represents a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, wherein R 3 and R 4 may together form a divalent organic group, R 5 each independently represents a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted C6-C10 aryl group, R 6represents a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 2 is R 1 O-N=CR 6 -represented by the group, R 1 CO-O-N=CR 6 -represented by the group, R 3 R 4 N-CO-O-N=CR 6 -represented by the group, R 3 R 4 N-N=CR 6 -represented by the group, or R 7 -N=CR 6 -represented by the group; R 1 R 3 R 4 and R 6 are the same as those in X 1 and represent the same meaning; R 7 represents a substituted or unsubstituted 5-membered heterocyclyl 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, or a substituted or unsubstituted C3-6 cycloalkylene group; Q represents a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-10 membered heterocyclyl group.

[0196] The symbols in formula (III) represent the same meaning as those in formula (II).

[0197] The compound represented by the following formula (IV) or its salt can be used as a production intermediate in the production of the compound represented by formula (II).

[0198]

Chemical formula

[0199] In formula (IV), X 1 is 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, a substituted or unsubstituted C3-6 cycloalkyloxy group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted C6-10 arylthio group, a substituted or unsubstituted C6-10 arylsulfinyl group, a substituted or unsubstituted C6-10 arylsulfonyl group, a substituted or unsubstituted 5-6 membered heterocyclyl group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group, a nitro group, a cyano group, R 1 -CO- group, a carboxy group, R 2 -O-CO- group, R 3 R 4 group represented by -N-, R 3 R 4 group represented by -N-CO-, R 1 group represented by -CO-O-, R 1 -CO-NR 5 group represented by - 2 group represented by -O-CO-O-, R 2 -O-CO-NR 5 group represented by - 3 R 4 group represented by -N-CO-O-, R 3 R 4 -N-CO-NR 5 group represented by - 2 SO 2 -NR 5 group represented by - 3 R 4 N-SO2 a group represented by -, or R 1 O-N=CR 6 represents a group represented by -; 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 5-6 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 5-6 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 5-6 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, wherein R 3 and R 4 may together 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 hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 2 is R 1 O-N=CR 6 -represents a group, R 1 CO-O-N=CR 6 -represents a group, R 3 R 4 N-CO-O-N=CR 6 -represents a group, R 3 R 4 N-N=CR 6 -represents a group, or R 7 -N=CR 6 -represents a group; R 1 , R 3 , R 4 , and R 6 have the same meaning as those in X 1 ; R 7 represents a substituted or unsubstituted 5-membered heterocyclyl group; X 3 represents a substituted or unsubstituted straight-chain C1-6 alkyl group, a substituted or unsubstituted straight-chain C2-6 alkenyl group, a substituted or unsubstituted straight-chain C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heterocyclyl group; X 4 represents a hydrogen atom or a C1-6 alkoxymethyl group.

[0200] Symbols other than X 4 in formula (IV) have the same meaning as those in formula (II). X 4As the "C1-6 alkoxy group" of the "C1-6 alkoxymethyl group", examples of the "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, an i-hexyloxy group, and the like.

[0201] An example of the production intermediate used in the production of the compound (II) of the present invention is shown in Table 1 below. In the table, the melting point (m.p.) is also shown as the physical property of each compound.

[0202]

Table 1

[0203] Among the compounds described in Table 1, for the compounds having an amorphous or viscous oil property, their 1 1H-NMR data are shown below. Compound 11: 1 1H-NMR (CDCl 3 ) 7.49(1H, s), 5.21-3.70(7H, m), 3.43(3H, s),2.16(3H, s), 1.35-1.20(9H, m).

[0204] 〔Fungicide for agriculture and horticulture〕 The fungicide for agriculture and horticulture of the present invention contains at least one selected from the compound (II) and its salts as an active ingredient. The amount of the compound (II) or its salt contained in the fungicide for agriculture and horticulture of the present invention is not particularly limited as long as it exhibits a bactericidal effect.

[0205] The fungicide for agriculture and horticulture of the present invention can be used for controlling plant diseases derived from a wide variety of filamentous fungi, for example, fungi belonging to Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, and Zygomycetes.

[0206] Examples of plant diseases (pathogenic fungi) to be controlled are shown below. Beet: Brown spot (Cercospora beticola), black root rot (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), leaf spot (Ramularia beticola), damping-off (Aphanomyces cochlioides, Pythium ultimum), etc. Peanut: Brown spot (Mycosphaerella arachidis), leaf spot (Ascochyta sp.), rust (Puccinia arachidis), damping-off (Pythium debaryanum), leaf spot (Alternaria alternata), southern blight (Sclerotium rolfsii), black leaf spot (Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc. Cucumber: Powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), gummy stem blight (Mycosphaerella melonis), fusarium wilt (Fusarium oxysporum), sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassiicola), damping-off (Pythium debaryanum, Rhizoctonia solani Kuhn), Phomopsis root rot (Phomopsis sp.), angular leaf spot (Pseudomonas syringae pv. Lachrymans), etc. Tomato: Gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans), Verticillium wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), early blight (Alternaria solani), Pseudocercospora leaf spot (Pseudocercospora fuligena), bacterial wilt (Ralstonia solanacearum), Sclerotinia rot (Sclerotinia sclerotiorum), etc. Eggplant: Gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), Mycosphaerella leaf spot (Mycovellosiella nattrassii), Sclerotinia rot (Sclerotinia sclerotiorum), Verticillium wilt (Verticillium dahliae), Phomopsis blight (Phomopsis vexans), etc. Pepper: Phytophthora blight (Phytophthora capsici), gray mold (Botrytis cinerea), Sclerotinia rot (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), Phytophthora crown rot (Phytophthora cactorum), soft rot (Rhizopus stolonifer), Fusarium wilt (Fusarium oxysporum), Verticillium wilt (Verticillium dahliae), Sclerotinia rot (Sclerotinia sclerotiorum), etc. Onions: Botrytis allii, Botrytis cinerea, Botrytis squamosa, Peronospora destructor, Phytophthora porri, Ciborinia allii, Botrytis squamosa, Fusarium oxysporum, Pyrenochaeta terrestris, Sclerotium cepivorum, Puccinia allii, Sclerotium rolfsii, etc. Leeks: Pectobacterium carotovorum, Peronospora destructor, Pleospora allii, Sclerotium cepivorum, Puccinia allii, Botrytis squamosa, Sclerotium rolfsii, Pyrenochaeta terrestris, etc. Cabbages: Plasmodiophora brassicae, Erwinia carotovora, Xanthomonas campestris pv. campestris, Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis, Peronospora parasitica, Sclerotinia sclerotiorum, Alternaria brassicicola, Botrytis cinerea, Phoma lingam, Pythium aphanidermatum, Pythium ultimum, Albugo macrospora, etc. Lettuce: rot diseases (Pseudomonas cichorii, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremia lactucae), gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum), big-vein disease (Mirafiori lettuce big-vein ophiovirus), root rot (Fusarium oxysporum), bottom rot (Rhizoctonia solani), powdery mildew (Golovinomyces orontii), etc. Kidney bean: sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), anthracnose (Colletotrichum lindemuthianum), angular leaf spot (Phaeoisariopsis griseola), etc. Pea: brown spot (Mycosphaerella blight), gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum), powdery mildew (Erysiphe pisi), etc.

[0207] Apple: Powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), brown rot (Monilinia mali), black spot (Mycosphaerella pomi), apple canker (Valsa mali), Alternaria blotch (Alternaria mali), rust (Gymnosporangium yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown leaf spot (Diplocarpon mali), sooty blotch (Zygophiala jamaicensis), flyspeck (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 (Rhizobium radiobacter, Rhizobium rhizogenes), etc. Plum: Scab (Cladosporium carpophilum), gray mold (Botrytis cinerea), brown rot (Monilinia mumecola), flyspeck (Peltaster sp.), pocket plum disease (Taphrina pruni), brown shot hole (Phloeosporella padi), etc. Persimmon: Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora kaki), round leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), sooty blotch (Zygophiala jamaicensis), etc. Peach: Brown rot (Monilinia fructicola, Monilia fructigena), shot hole (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), bacterial leaf spot (Xanthomonas campestris pv. pruni), leaf curl (Taphrina deformans), anthracnose (Colletotrichum gloeosporioides), brown leaf blotch (Phloeosporella padi), turkey tail (Coriolus versicolor), etc. Almond: Brown rot (Monilinia laxa), stigma rot (Stigmina carpophila), shot hole (Cladosporium carpophilum), leaf blister (Polystigma rubrum), Alternaria leaf spot (Alternaria alternata), anthracnose (Colletotrichum gloeospoides), etc. Plum: Brown rot (Monilinia fructicola), anthracnose (Colletotrichum acutatum), Alternaria leaf spot (Alternaria sp.), Monilinia core rot of young fruit (Monilinia kusanoi), brown leaf blotch (Mycosphaerella cerasella), powdery mildew (Podosphaera tridactyla), etc. Grape: Gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), anthracnose (Elsinoe ampelina), brown leaf spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), white fluffy mildew (pathogen not identified), crown gall (Rhizobium radiobacter, Rhizobium vitis), etc. Pear: Venturia nashicola, Gymnosporangium asiaticum, Alternaria kikuchiana, Botryosphaeria berengeriana, Phyllactinia mali, Phomopsis fukushii, Stemphylium vesicarium, Glomerella cingulata, etc. Tea: Pestalotiopsis longiseta, P. theae, Colletotrichum theae-sinensis, Exobasidium reticulatum, Pseudomonas syringae, Exobasidium vexans, etc. Citrus: Elsinoe fawcettii, Penicillium italicum, Penicillium digitatum, Botrytis cinerea, Diaporthe citri, Xanthomonas campestris pv. Citri, Oidium sp., Phytophthora citrophthora, Colletotrichum fioriniae, etc. Kiwi fruit: Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava, Pseudomonas syringae, Botrytis cinerea, Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae, Pseudocercospora actinidiae, etc. Olive: Anthracnose (Colletotrichum acutatum, Colletotrichum gloeosporioides), Peacock spot (Spilocaea oleaginea), etc. Chestnut: Anthracnose (Colletotrichum gloeosporioides), etc.

[0208] 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), Pink snow blight (Monographella nivalis), Eyespot (Pseudocercosporella herpotrichoides), Septoria leaf blotch (Septoria tritici), Stagonospora nodorum blotch (Leptosphaeria nodorum), Snow mold (Typhula incarnata), Large snow mold (Myriosclerotinia borealis), Take-all (Gaeumannomyces graminis), Ergot (Claviceps purpurea), Loose smut (Tilletia caries), Naked smut (Ustilago nuda), Rice blast (Pyricularia grisea), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Barley: Leaf stripe (Pyrenophora graminea), net blotch (Pyrenophora teres), scald (Rhynchosporium secalis), loose smut (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), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium graminicola), bacterial blight (Xanthomonas oryzae), seedling blight caused by bacteria (Burkholderia plantarii), brown stripe (Acidovorax avenae), bakanae disease caused by bacteria (Burkholderia glumae), leaf streak (Cercospora oryzae), false smut (Ustilaginoidea virens), brown rice (Alternaria alternata, Curvularia intermedia), black-bellied rice (Alternaria padwickii), red-colored rice (Epicoccum purpurascens), etc. Tobacco: Sclerotinia rot (Sclerotinia sclerotiorum), powdery mildew (Erysiphe cichoracearum), Phytophthora blight (Phytophthora nicotianae), etc. Tulip: Gray mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf rot (Rhizoctonia solani), bulb rot (Fusarium oxysporum), skin rot (Rhizoctonia solani), etc. Rose: 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), damping-off (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), Rhizoctonia blight (Rhizoctonia solani), Fusarium blight (Fusarium solani), etc. Gerbera: Gray mold (Botrytis cinerea), powdery mildew (Podosphaera xanthii), etc. Lily: Leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc. Sunflower: Downy mildew (Plasmopara halstedii), Sclerotinia rot (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), etc. Kentucky bluegrass: Snow rot sclerotinia (Sclerotinia borealis), large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), damping-off (Pythium aphanidermatum), anthracnose (Colletotrichum graminicola), etc. Orchardgrass: Powdery mildew (Erysiphe graminis), etc. Soybean: Purple blotch (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 spot (Elsinoe glycines), black dot (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), early blight (Alternaria solani), black scurf (Thanatephorus cucumeris), Verticillium wilt (Verticillium albo - atrum, V. dahliae, V. nigrescens), black leg (Pectobacterium atrosepticum), soft rot (Pectobacterium carotovorum), gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia rot (Sclerotinia sclerotiorum), etc. Yam: 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: Blight (Phytophthora colocasiae), stem rot (Rhizoctonia solani), etc. Ginger: Rhizome rot (Pythium ultimum, Pythium myriotylum), Leaf spot (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum aenigma), Bacterial canker (Xanthomonas campestris), Stem-end rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), Gray mold (Botrytis cinerea), etc. Rape: Sclerotinia rot (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 spot (Cercospora coffeicola), etc. Sugarcane: Brown rust (Puccinia melanocephala), etc. Maize: Leaf blight (Gloeocercospora sorghi), rust (Puccinia sorghi), southern rust (Puccinia polysora), smut (Ustilago maydis), leaf spot (Cochliobolus heterostrophus), northern leaf blight (Setosphaeria turcica), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Cotton: Damping off (Pythium sp.), rust (Phakopsora gossypii), leaf spot (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hop: Downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.

[0209] [Nemacide] The dihydropyrimidine compound of the present invention is also excellent in the control effect of various nematodes that affect plant growth. The nemacide of the present invention contains at least one selected from compound (II) and its salts as an active ingredient. The amount of compound (II) or its salts contained in the nemacide of the present invention is not particularly limited as long as it exhibits a nematode control effect.

[0210] Specific examples of various plant-parasitic nematodes that can be controlled by the nemacide of the present invention are shown below. (1) Order Tylenchida (a) From the family Anguinidae, for example, species of the genus Anguina such as Anguina funesta, Anguina tritici; species of the genus Ditylenchus such as Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus; (b) From the family Aphelenchoididae, for example, species of the genus Aphelenchoides such as Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi, Aphelenchoides besseyi; species of the genus Bursaphelenchus such as Bursaphelenchus xylophilus; (c) From the family Belonolaimidae, for example, species of the genus Belonolaimus such as Belonolaimus longicaudatus; species of the genus Tylenchorhynchus such as Tylenchorhynchus claytoni, Tylenchorhynchus dubius; (d) From the family Criconematidae, for example, Criconema mutabile; (e) From the family Dolichodoridae, for example, Dolichodorus mediterraneus; (f) of the family Ecphyadophoridae, for example, Ecphyadophora tenuissima (g) of the family Hemicycliophoridae, for example, Loofia thienemanni; (h) of the family Heteroderidae, for example, of the genus Globoderarostochiensis, Globodera pallida, Globodera tabacum of the genus Globoderaspp.; of the genus Heterodera spp., Heterodera avenae, Heterodera cruciferae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii; (i) of the family Hoplolaimidae, for example, of the genus Helicotylenchus spp., Helicotylenchus dihystera, Helicotylenchus multicinctus; of the genus Hoplolaimus spp., Hoplolaimus columbus, Hoplolaimus galeatus; other, Rotylenchus robustus, Rotylenchulus reniformis; (j) of the family Meloidogynidae, such as of the genus Meloidogyne spp., Meloidogyne arenaria, Meloidogyne chitwoodi, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne thamesi; (k) of the family Nothotylenchidae, such as Nothotylenchus acris; (l) of the family Paratylenchidae, such as of the genus Paratylenchus spp., Paratylenchus curvitatus, Paratylenchus elachistus; (m) Pratylenchidae, for example, Pratylenchus spp. such as Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus curvitatus, Pratylenchus fallax, Pratylenchus goodeyi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus scribneri, Pratylenchus vulnus, Pratylenchus zeae; other nematodes such as Nacobbus aberrans, Radopholus similis, Tylenchulus semipenetrans, Radopholus citrophilus.

[0211] (2) Order Dorylaimida (a) Longidoridae, for example, Longidorus spp. such as Longidorus elongates; Xiphinema spp. such as Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Xiphinema diversicaudatum.

[0212] (3) Order Triplonchida (a) For example, Trichodorus primitivus and Paratrichodorus minor of the family Trichodoridae.

[0213] 〔Application method · Mixture〕 The fungicide or nematicide for horticulture and agriculture of the present invention is preferably used for plants such as cereals, vegetables, root vegetables, tubers, fruit trees, trees such as tea, coffee, and cacao, forage grasses, turfgrasses, and cotton.

[0214] The fungicide for horticulture and agriculture of the present invention can be applied to each part of plants, such as leaves, stems, petioles, flowers, buds, fruits, seeds, sprouts, roots, tubers, rhizomes, cuttings, etc. The nematicide can be applied to roots, tubers, rhizomes, etc. In addition, improved varieties, variants, cultivars, and even mutants, hybrids, and genetically modified organisms (GMOs) of these plants can also be targeted.

[0215] The fungicide for horticulture and agriculture of the present invention can be used for seed treatment, foliar spraying, soil application, water surface application, etc. for controlling various diseases occurring in horticultural crops including flowers, turfgrasses, and forage grasses. The nematicide can be used for seed treatment, soil application, etc.

[0216] The fungicide or nematicide for horticulture and agriculture of the present invention may contain components other than the dihydropyrimidine compound of the present invention. Examples of other components include known carriers used for formulation. In addition, examples of other components include conventionally known fungicides, insecticide / acaricides, nematicides, soil pest control agents, plant regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. By containing such other components, a synergistic effect may be achieved. That is, as one aspect of the present invention, a fungicide for horticulture and agriculture containing one or more additional fungicides can be mentioned.

[0217] Specific examples of fungicides that can be mixed or used in combination with the agricultural and horticultural fungicide or nematicide of the present invention are shown below. (1) Nucleic acid biosynthesis inhibitors: (a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl; crozylacon, ofurace; (b) Adenosine deaminase inhibitors: bupirimate, dimethirimol, ethirimol; (c) DNA / RNA synthesis inhibitors: hymexazol, octhilinone; (d) DNA topoisomerase II inhibitors: oxolinic acid.

[0218] (2) Mitosis inhibitors and cell division inhibitors: (a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorfenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; diethofencarb; zoxamide; ethaboxam; (b) Cell division inhibitors: pencycuron; (c) Inhibitors of delocalization of spectrin-like proteins: fluopicolide, fluopyramide.

[0219] (3) Respiration inhibitors: (a) Complex I-NADH oxidoreductase inhibitors: diflumetorim; tolfenpyrad; (b) Complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil; isofetamid; fluopyram; fenfuram, flumequin; carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluxapyroxad, flutopirazine, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid, pidiflumetofen, isoflurazole, pyraziflumid, inpyrfluxam; (c) Complex III - ubiquinol oxidase Qo inhibitors: azoxystrobin, coumoxystrobin, kresoxim - methyl, enoxastrobin, fluoxastrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin, pyrametostrobin, triclopyricarb; cresoxim - methyl, trifloxystrobin; dimoxystrobin, phenaminostrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyriminobac - methyl; methyltetraprole; mandestrobin; (d) Complex III - ubiquinol reductase Qi inhibitors: cyazofamid; amisulbrom; fenpicoxamid; (e) Uncouplers of oxidative phosphorylation: binapacryl, meptyldinocap, dinocap; fluazinam; ferimzone; (f) Inhibitors of oxidative phosphorylation (inhibitors of ATP synthase): fen tin acetate, fen tin chloride, fen tin hydroxide; (g) ATP production inhibitors: silthiopham; (h) Complex III: Qx (unknown) inhibitors of cytochrome bc1 (ubiquinone reductase): ametoctradin.

[0220] (4) Amino acid and protein synthesis inhibitors: (a) Methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil; (b) Protein synthesis inhibitors: blasticidin - S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.

[0221] (5) Signal transduction inhibitors: (a) Signal transduction inhibitors: quinoxyfen, proquinazid; (b) MAP - histidine kinase inhibitors in osmotic signal transduction: fenpiclonil, fludioxonil; chlorothalonil, iprodione, procymidone, vinclozolin.

[0222] (6) Lipid and cell membrane synthesis inhibitors: (a) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos; isoprothiolane; (b) Lipid peroxidants: biphenyl, chloroneb, dicloran, quintozene, tecnazene, toclofos-methyl; etridiazole; (c) Agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb; (d) Microorganisms disrupting pathogen cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain; (e) Agents disrupting cell membranes: extract of Melaleuca alternifolia (tea tree).

[0223] (7) Sterol biosynthesis inhibitors of cell membranes: (a) Inhibitors of C14 demethylation in sterol biosynthesis: triafolin; pyrifenox, pyrisoxazole; fenarimol, flurprimidol, nuarimol; imazalil, imazalil sulfate, oxpoconazole, pefurazoate, prochloraz, triflumizole, viniconazole; azaconazole, bitertanol, bromoconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole, mefentrifluconazole; (b) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperalin; spiroxamine; (c) 3-ketoreductase inhibitors in the C4-demethylation of the sterol biosynthetic pathway: fenhexamide; fenpyrazamine; (d) Squalene epoxidase inhibitors in the sterol biosynthetic pathway: pyributicarb; naftifine, terbinafine.

[0224] (8) Cell wall synthesis inhibitors: (a) Trehalase inhibitors: validamycin; (b) Chitin synthase inhibitors: polyoxin, polyoxorim; (c) Cellulose synthase inhibitors: dimethomorph, flumorph, pyrimorph; benzov alicarb, iprovalicarb, valifenalate; mandipropamid.

[0225] (9) Melanin biosynthesis inhibitors (a) Reductase inhibitors of melanin biosynthesis: fusaride; pyroquilon; tricyclazole; (b) Dehydratase inhibitors of melanin biosynthesis: carpropamid; diclocymet; phenoxanil; (c) Polyketide synthase inhibitors of melanin biosynthesis: tolprocarb.

[0226] (10) Inducers of host plant resistance: (a) Agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl; (b) Others: probenazole, thiazinyl, isothiazinyl, dichlobenzox, ipfentrifluconazole, laminarin, extract of Saururus chinensis.

[0227] (11) Agents with unknown mode of action: simoxanil, fosetyl aluminum, phosphoric acid (phosphate), tecnazene, triazoxide, flusulfamide, diclomezine, methiocarb, diflufenican, metrafenone, pyriofenone, dodine, dodine free base, flutianil.

[0228] Agents with multiple sites of action: copper (copper salts), Bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, dinneb, ziram; captan, captophore, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; quinomethionate; fluoroimide.

[0229] (13) Other agents: DBEDC, fluorfolpet, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, cyprofuram, Agrobacterium, benzoxazin, diphenylamine, methyl isothiocyanate (MITC), mildeomycin, capsaicin, cupravit, cyprosulfamide, dazomet, decarb, dichlorophene, diphenzoquat, diphenzoquat methyl sulfonate, flumetover, fosetyl calcium, fosetyl sodium, irumamycin, natamycin, nitrotal isopropyl, oxamocarb, pyrrolnitrin, tebufloquin, tolfenpyrad, zarilamide, Algophase, Amicarthiazol, Oxathiapiprolin, fluoxapiprolin, metiram zinc, benzthiazole, triclopyricarb, uniconazole, oxyfenthiin, picarbutrazox, quinofumelin, florylpicoxamid, pyrapropoyne, fluindapyr, aminopyrifen, pyridachlomethyl, ipflufenoquin, diphenamidtron.

[0230] Specific examples of insecticides, acaricides, nematicides, soil pest control agents, anthelmintics, etc. that can be mixed or used in combination with the fungicide or nematicide for agricultural and horticultural use of the present invention are shown below. (1A) Acetylcholinesterase (AChE) inhibitor (carbamate-based): Allanearb, Aldicarb, Bendicarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Phenobucarb, Formetanate, Furathiocarb, Isopropcarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pyrimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, Xylylcarb.

[0231] (1B) Acetylcholinesterase (AChE) inhibitor (organophosphate-based): Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Kazusaphos, Chloretoxyphos, Chlorfenvinphos, Chloromethiophos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Dimethoate-S-methyl, Diazinon, Dichlorvos, Dichlorothophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Etofiprole, Fanfur, Fenamiphos, Fenitrothion, Fenthion, Phosphamidon, Heptenophos, Imicyafos, Isofenphos, Isopropyl = O-(methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Horate, Hosalone, Phosmet, Phosphamidon, Hoxim, Pyrimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridafenthion, Quinalphos, Sulfotepp, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thimeton, Triazophos, Trichlorfon, Bamidothion.

[0232] (2) GABA-activated chloride ion (chloride ion) channel blocker: Chlordene, endosulfan; ethiprole, fipronil. Flufiprole. (3A) Sodium channel modulators (pyrethroids): Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin. kappa-bifenthrin, chloroprallethrin, heptafluthrin, meperfluthrin, epsilon-methofluthrin, monofluoroethrin, epsilon-monofluoroethrin, kappa-tefluthrin, tetramethylfluthrin; bioethanomethrin. (3B) Sodium channel modulators (DDT analogs): DDT, methoxychlor.

[0233] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators: Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; nicotine; sulfoxaflor; flupyradifurone; triflumizopyrim. Dichloromethothiaz, flupyrimin. (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators: Spinetram, spinosad. (6) Glutamate-gated chloride ion (chloride ion) channel (GluCl) allosteric modulators: Abamectin, emamectin, emamectin benzoate, lepimectin, milbemectin. Doramectin, eprinomectin, ivermectin, moxidectin, selamectin. (7) Juvenile hormone analogs: Hydroprene, kinoprene, methoprene; phenoxycarb; pyriproxyfen. (8) Other non-specific (multi-site) inhibitors: Methyl bromide, alkyl halides; chloropicrin; sodium aluminum fluoride, sulfuryl fluoride; borax, boric acid, disodium octaborate tetrahydrate, sodium borate, sodium metaborate; tartar emetic; dazomet, metam, potassium metam, sodium metam. (9) Chordotonal organ TRPV channel modulators: Pymetrozine, pyrifluquinazone; afidopyropen.

[0234] (10) Mite growth inhibitors: Clofentezine, diflovidazin, hexythiazox; etoxazole. (11) Microbe-derived insect midgut intima disruptors: B.t. subsp. israelensis, B.t.subsp. aizawai, B.t. subsp. kurstaki, B.t. subsp. tenebrionis; Proteins contained in B.t. crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus. (12) Mitochondrial ATP synthase inhibitors: Diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide; propargite; tetradifon. (13) Oxidative phosphorylation uncoupling agents that disrupt the proton gradient: Chlorfenapyr, DNOC, Sulfuramid. (14) Nicotinic acetylcholine receptor (nAChR) channel blockers: Bensultap, Cartap hydrochloride, Thiocyclam, Thiosultap - sodium salt. (15) Chitin biosynthesis inhibitors, type 0: Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron. (16) Chitin biosynthesis inhibitors, type 1: Buprofezin. (17) Molting inhibitors: Cyromazine. (18) Ecdysone receptor agonists: Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide. (19) Octopamine receptor agonists: Amitraz.

[0235] (20) Mitochondrial electron transport chain complex III inhibitors: Hydramethylnon; Acequinocyl; Fluacrypyrim; Bifenazate. (21) Mitochondrial electron transport chain complex I inhibitors (METI): Phenazakine, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad; Rotenone. (22) Voltage - dependent sodium channel blockers: Indoxacarb; Metaflumizone. (23) Acetyl - CoA carboxylase inhibitors: Spirodiclofen, Spirotetramat, Spirodiclofen. Spiropidion. (24) Mitochondrial electron transport chain complex IV inhibitors: Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine; calcium cyanide, sodium cyanide, potassium cyanide. (25) Mitochondrial electron transport system complex II inhibitor: Cyenopyrafen, cyflumetofen; piflubumide. (28) Ryanodine receptor modulator: Chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide. Cyhalodiamide, tetrachlorantraniliprole, tetraniliprole. (29) Chordotonal organ modulator, target site unspecified: Flonicamid. (30) GABAergic chloride ion channel allosteric modulator: Brofanilide, fluxametamide. Isocycloseram; afoxolaner, fluralaner, lotilaner, sarolaner. Other insecticides, acaricides: Azadirachtin, benzoximate, bromopropylate, quinomethionate, dicofol, lime sulfur, mancozeb, pyridalyl, sulfur. Acinonapil, benzpyramoxan, flometokine, fluphenhexone, oxathiosulfyl, ticlopyrazoflor.

[0236] Anthelmintics: (a) Benzimidazole series: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, parbendazole, flubendazole; febantel, netobimin, thiophanate; thiabendazole, cambendazole; (b) Salicylanilide series: closantel, oxyclozanide, rafoxanide, niclosamide; (c) Substituted phenol series: nitroxynil, nitrosacaneate; (d) Pyrimidine series: pyrantel, morantel; (e) Imidazothiazole series: levamisole, tetramisole; (f) Tetrahydropyrimidine series: Praziquantel, Epsiprantel; (g) Other anthelmintics: Cyclodiene, Ryania, Chlorothalonil, Metronidazole, Demiditraz; Piperazine, Diethylcarbamazine, Dichlorophene, Monepantel, Triclabendazole, Amidantel; Thiacetarsamide, Melarsomine, Arsenamide.

[0237] Specific examples of plant regulators that can be mixed or used in combination with the agricultural and horticultural fungicides or nematicides of the present invention are shown below. Abscisic acid, Kinetin, Benzylaminopurine, 1,3-Diphenylurea, Forchlorfenuron, Thidiazuron, Chlorfenuron, Dihydrozeatin, Gibberellin A, Gibberellin A4, Gibberellin A7, Gibberellin A3, 1-Methylcyclopropane, N-Acetylaminoethoxyvinylglycine (alias: Aviglycine), Aminooxyacetic acid, Silver nitrate, Cobalt chloride, IAA, 4-CPA, Clopropp, 2,4-D, MCPB, Indole-3-butyric acid, Dichlorprop, Phenothiol, 1-Naphthylacetamide, Ethychlozate, Croxyphonaque, Maleic hydrazide, 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.

[0238] 〔Formulation prescription〕 The agricultural and horticultural fungicides or nematicides of the present invention are not particularly limited by dosage form. For example, dosage forms such as wettable powders, emulsions, powders, granules, water-soluble agents, suspensions, granular wettable powders, tablets, etc. can be mentioned. The preparation method for the formulation is not particularly limited, and a known preparation method can be adopted according to the dosage form. Some formulation examples are shown below. The formulation prescriptions shown below are merely illustrative and can be modified within the scope not contrary to the gist of the present invention. The present invention is not limited by the following formulation examples in any way. "Part" means "part by weight" unless otherwise specified.

[0239] (Formulation Example 1: Wettable Powder) 40 parts of the dihydropyrimidine compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate ester, and 3 parts of alkylnaphthalenesulfonate are uniformly mixed and finely pulverized to obtain a wettable powder with 40% active ingredient. (Formulation Example 2: Emulsion) 30 parts of the dihydropyrimidine compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion with 30% active ingredient. (Formulation Example 3: Granule) 5 parts of the dihydropyrimidine compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed, finely pulverized, and then granulated to a particle diameter of 0.5 - 1.0 mm to obtain a granule with 5% active ingredient. (Formulation Example 4: Granule) 5 parts of the dihydropyrimidine compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctyl sulfosuccinate, and 1 part of potassium phosphate are uniformly mixed and pulverized. Water is added thereto and kneaded well, and then granulated and dried to obtain a granule with 5% active ingredient. (Formulation Example 5: Suspension) 10 parts of the dihydropyrimidine compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylate salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water are mixed and wet-pulverized until the particle size becomes 3 microns or less to obtain a suspension with 10% active ingredient. (Formulation Example 6: Granular Wettable Powder) 40 parts of the dihydropyrimidine compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzenesulfonate, 8 parts of sodium ligninsulfonate, and 5 parts of a formaldehyde condensate of sodium alkylbenzenesulfonate are uniformly mixed, finely pulverized, and then an appropriate amount of water is added and kneaded to form a clay-like substance. The clay-like substance is granulated and then dried to obtain a wettable granule containing 40% of the active ingredient.

[0240] 〔Medical and veterinary antifungal agents〕 The dihydropyrimidine compound of the present invention can be used as a prophylactic agent and a therapeutic agent for controlling harmful pathogenic bacteria, particularly fungi, that infect humans or animals. The medical and veterinary antifungal agent of the present invention contains at least one selected from compound (II) and its salts as an active ingredient. The amount of compound (II) or its salt contained in the medical antifungal agent of the present invention is not particularly limited as long as it exhibits an antifungal effect.

[0241] As used herein, the term "animal" means vertebrates (Vertebrata) such as pets, livestock, poultry, exhibition animals kept in zoos and aquariums, captured wild animals, and research and experimental animals.

[0242] For example, the following animals can be mentioned, but the specific examples of animals are not limited to these. Mammals such as sheep, goats, pigs, horses, cows, guinea pigs, donkeys, mules, camels, llamas, alpacas, wild boars, reindeer, deer, mink, elephants, bears, kangaroos, foxes, dogs, cats, squirrels, rabbits, mice, rats, guinea pigs, hamsters, monkeys, ferrets, etc. Birds such as pigeons, parrots, crows, peacocks, cedar waxwings, canaries, chickens, ducks, butterflies, wild ducks, pheasants, peacocks, ostriches, swans, sparrows, quails, owls, eagles, falcons, seagulls, etc. Reptiles such as chameleons, iguanas, lizards, snakes, turtles, crocodiles, geckos, etc. Amphibians such as frogs, newts, etc. Fish such as carp, goldfish, medaka, tropical fish, yellowtail, amberjack, sea bass, salmon, mackerel, sea bream, tuna, horse mackerel, flounder, pufferfish, etc.

[0243] Examples of pathogenic fungi (molds) for which the medical and veterinary antifungal agent of the present invention can be applied are shown below. Note that the specific examples are not limited to only these. For example, the genus Absidia such as Absidia corymbifera; the genus Acremonium; the genus Alternaria such as Alternaria alternata; the genus Aspergillus such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, Aspergillus parasiticus, Aspergillus terreus; the genus Bipolaris; 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, Candida tropicalis; the genus Cladosporium such as Cladosporium cladosporoides, Cladosporium herbarium; the genus Coccidioides such as Coccidioides immitis, Coccidioides posadasii; the genus Colletotrichium such as Colletotrichium trifolii; the genus Cryptococcus such as Cryptococcus neoformans; the genus Curvularia such as Curvularia lunata; the genus Encephalitozoon such as Encephalitozoon cuniculi; the genus Epicoccum such as Epicoccum nigrum; the genus Epidermophyton such as Epidermophyton floccosum; the genus Exophiala; the genus Exserohilum such as Exserohilum rostratum; the genus Fusarium such as Fusarium graminarium, Fusarium solani, Fusarium sporotrichoides; the genus Fonsecaea such as Fonsecaea monophora; the genus Histoplasma such as Histoplasma capsulatum;Genus Leptosphaeria such as Leptosphaeria nodorum; Genus Malassezia such as Malassezia globosa; Genus Microsporum such as Microsporum canis; Genus Mycosphaerella such as Mycosphaerella graminicola; Genus Neurospora; Genus Paecilomyces such as Paecilomyces lilanicus, Paecilomyces varioti; Genus Penicillium such as Penicillium chrysogenum; Genus Phytophthora such as Phytophthora capsici, Phytophthora infestans; Genus Plasmopara such as Plasmopara viticola; Genus Pneumocystis such as Pneumocystis jirovecii; Genus Pyricularia such as Pyricularia oryzae; Genus Pythium such as Pythium ultimum; Genus Puccinia such as Puccinia coronata, Puccinia graminis; Genus Rhizoctonia such as Rhizoctonia solani; Genus Rhizomucor; Genus Scedosporium such as Fusarium apiospermum, Scedosporium prolificans; Genus Scopulariopsis such as Scopulariopsis brevicaulis; Genus Sporothrix such as Sporothrix schenckii; Genus Talaromyces such as Talaromyces marneffei, Genus Trichophyton such as Trichophyton mentagrophytes, Trichophyton interdigitale, Trichophyton rubrum, Trichophyton tonsurans, Trichophyton verrucosum; Genus Trichosporon such as Trichosporonasahii, Trichosporon beigelii; Genus Ustilago etc.; Among these, the antifungal agent of the present invention is suitable for Aspergillus, Trichophyton or Candida, and particularly suitable for Aspergillus fumigatus or Trichophyton tonsurans.

[0244] Examples of infectious diseases to which the medical and veterinary antifungal agents of the present invention can be applied are shown below. Note that the specific examples are not limited to these only.

[0245] The medical and veterinary antifungal agents of the present invention can be applied to any of systemic fungal infections, superficial fungal infections, etc. Specific examples of fungal infections include Aspergillus infections such as pulmonary aspergillosis, systemic aspergillosis (which is likely to occur in immunosuppressed patients such as bone marrow recipients or AIDS patients), Candida infections such as systemic candidiasis, Cryptococcus meningitis, rhinocerebral mucomycosis, pulmonary mucomycosis, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, lobomycosis, corneal mycosis, sporotrichosis, chromoblastomycosis, chromomycosis, phaeohyphomycosis, zygomycosis, cryptococcosis, disseminated sporotrichosis, ringworm, tinea capitis, tinea corporis, tinea cruris, tinea pedis, onychomycosis, cutaneous, oral, or vaginal candidiasis, Malassezia infection, chronic mucocutaneous candidiasis, Pneumocystis pneumonia, Penicillium marneffei infection, etc. In addition, the antifungal agent of the present invention is also applicable to allergic diseases caused by fungi, for example, allergic bronchopulmonary asthma (ABPA); asthma, rhinosinusitis, or paranasal sinusitis, etc.

[0246] The antifungal agent for medical and animal use of the present invention can contain pharmaceutically acceptable additives. The additives are not particularly limited as long as they are those used in known medical agents. Naturally, these are sterile and non-pyrogenic. Also, the additives can be appropriately selected according to the dosage form and administration method of the antifungal agent, etc.

[0247] The dosage forms that the antifungal agent for medical and animal use of the present invention can take are not particularly limited. For example, solid agents such as tablets, powders, granules, pellets, capsules, troches (lozenges), pellets, etc.; liquid agents such as syrups, emulsions, suspensions, solutions, pour-on agents, spot-on agents, etc.; semi-solid preparations such as ointments, gels, etc.; gaseous agents such as aerosols, vapors, etc.; nanoparticle preparations, etc. can be mentioned. The administration of the antifungal agent for medical use of the present invention can be carried out by known methods. Examples of the administration method include injection such as subcutaneous, intravenous, intramuscular, intrasternal, etc.; percutaneous administration such as insertion into the anus, vagina, etc., application or spraying on the skin surface, dropping, etc.; oral administration such as taking by mouth; nasal administration by inhalation, etc.

[0248] In the case of solid preparations for oral administration, additives that can be used in the antifungal agents for medical and veterinary use 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, polyethylene glycol, etc.; binders such as starch, arabic gums, gelatin, methyl cellulose, carboxymethyl cellulose or polyvinyl pyrrolidone; disaggregating agents such as starch, alginic acid, alginates or sodium glycolate starch; effervescing mixtures; pigments; sweeteners; wetting agents such as lecithin, polysorbate, lauryl sulphates; or non-toxic and pharmacologically inert substances generally used in pharmaceutical preparations, etc. These additives can be incorporated into the antifungal agents for medical use of the present invention by known methods such as mixing, granulating, tableting, sugar coating, or film coating.

[0249] In the case of liquid preparations for oral administration, additives that can be used in the antifungal agents for medical and veterinary use of the present invention include solubilizing agents such as cyclodextrin or modified cyclodextrin, sucrose, glycerin, mannitol, sorbitol, natural gums, agar, sodium alginate, pectin, methyl cellulose, carboxymethyl cellulose, or polyvinyl alcohol, etc.

[0250] In the case of liquid preparations for intramuscular injection, additives that can be used in the antifungal agents for medical and veterinary use of the present invention include sterilized water, olive oil, ethyl oleate, glycols such as propylene glycol, solubilizing agents such as cyclodextrin, modified cyclodextrin, etc. Furthermore, an appropriate amount of lidocaine hydrochloride can be included if necessary.

[0251] In the case of a liquid preparation for intravenous injection, examples of additives that can be used in the antifungal agent for medical and veterinary use of the present invention include carriers such as sterilized water; solubilizing agents such as cyclodextrin and modified cyclodextrin. These can also be included in the form of a sterilized isotonic physiological saline aqueous solution.

[0252] The amount of compound (II) 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 antifungal agent for medical and veterinary use of the present invention can be appropriately selected according to the administration method, the type of fungus infected, the age, body weight, symptoms, etc. of the patient. For example, for adults, in the case of oral or parenteral (injection, drip, etc.) administration, it can be administered at 0.1 to 100 mg / kg-body weight once or several times a day. In addition, the antifungal agent for medical and veterinary use of the present invention can be used in combination with other drugs other than compound (II).

[0253] Next, synthesis examples are shown to more specifically explain the present invention. However, the present invention is not limited by the following synthesis examples at all. 〔Example 1〕 Synthesis of 2-(3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-((isopropoxyimino)methyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide (Compound No. A-14) (Step 1) Synthesis of 2-(5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide

[0254]

Chemical formula

[0255] 5-(((tert-Butyldimethylsilyl)oxy)methyl)pyrimidine-2,4(1H,3H)-dione (1.50 g) was dissolved in N,N-dimethylformamide (60 ml). Under ice-cooling, potassium carbonate (0.81 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (1.45 g) were added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the resulting solid was filtered off. The obtained solid was dissolved in N,N-dimethylformamide (60 ml), potassium carbonate (0.98 g) and 2-bromo-N-isopropylpropanamide (1.40 g) were added, and the mixture was stirred at 45 °C overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 2.13 g of the target compound. Yield 68% Of the obtained target product 1 1H-NMR is shown below. 1 1H-NMR (CDCl 3 ) δ: 7.63 - 6.97 (3H, m), 7.08 (1H, s), 5.47 - 5.01 (4H, m), 4.54 (2H, s), 4.10 - 4.03 (1H, m), 3.98 (3H, s), 1.61 (3H, d), 1.12 (6H, d), 0.91 (9H, s), 0.12 (6H, s) (Step 2) Synthesis of 2-(5-(((tert-butyldimethylsilyl)oxy)methyl)-3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide

[0256] [Chemical]

[0257] 2-(5-(((tert-Butyldimethylsilyl)oxy)methyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide (0.15 g) was dissolved in methanol (1.5 ml) and tetrahydrofuran (1.5 ml), and sodium borohydride (12 mg) was added under ice-cooling, followed by stirring for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was dissolved in tetrahydrofuran (1.5 ml). Acrylonitrile (0.2 g) and a 40% aqueous potassium hydroxide solution (0.1 ml) were added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with chloroform and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 0.08 g of the target compound. Yield: 48% Of the obtained target product 1 1H-NMR is shown below. 1 1H-NMR (CDCl 3 ) δ: 7.19 - 6.82 (4H, m), 5.82 - 5.07 (3H, m), 4.49 (2H, s), 4.20 - 3.41 (5H, m), 3.82 (3H, s), 2.53 (2H, t), 1.55 (3H, d), 1.12 (6H, d), 0.91 (9H, s), 0.12 (6H, s) (Step 3) Synthesis of 2-(3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-((isopropoxyimino)methyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide

[0258]

Chemical formula

[0259] 2-(5-(((tert-Butyldimethylsilyl)oxy)methyl)-3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)-N-isopropylpropanamide (2.00 g) was dissolved in tetrahydrofuran (8 ml) and water (8 ml), acetic acid (20 ml) was added, and the mixture was stirred at room temperature for 7 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was dissolved in chloroform (80 ml), manganese dioxide (2.00 g) was added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was filtered, the mother liquor was concentrated, and the obtained residue was dissolved in chloroform (20 ml) and ethanol (20 ml). Pyridine (0.40 g) and isopropoxyamine hydrochloride (0.6 g) were added at room temperature, and the mixture was stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 1.26 g of the target compound (E:Z = 1:1). Yield 70% For the obtained target product 1 1H-NMR is shown below. 1 1H-NMR (CDCl 3) δ: 8.84 - 7.51 (2H, m) 7.14 - 6.80 (3H, m), 5.85 - 5.07 (3H, m), 4.40 - 3.41 (6H, m), 3.82 (3H, s), 2.65 - 2.51 (2H, m), 1.55 (3H, d), 1.29 - 1.13 (12H, m)

[0260] [Example 2] Synthesis of N-(2-(3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-(1-(ethoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (Compound No. A-38) (Step 1) Synthesis of tert-butyl(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)carbamate

[0261] [Chemical formula]

[0262] 5-Acetyluracil (2.50 g) was dissolved in N,N-dimethylformamide (80 ml). Under ice-cooling, potassium carbonate (2.20 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (4.00 g) were added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the resulting solid was filtered. The obtained solid was dissolved in N,N-dimethylformamide (120 ml), potassium carbonate (2.40 g) and tert-butyl N-(2-bromoethyl)carbamate (4.80 g) were added, and the mixture was stirred at 80 °C for 5 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 4.60 g of the target compound. Yield 61% Of the obtained target product 1 The 1H-NMR is shown below. 1 1H-NMR (CDCl 3 ) δ: 8.09 (1H, s), 7.64 - 6.99 (3H, m), 5.21(2H, s), 4.87 (1H, m), 4.17 - 3.42 (4H, m), 4.00 (3H, s), 2.65(3H, s), 1.40 (9H,s) (Step 2) Synthesis of N-(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide

[0263]

Chemical Structure

[0264] tert-butyl(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)carbamate (1.60 g) was dissolved in 1,4-dioxane (50 ml), and 4 N hydrogen chloride / 1,4-dioxane solution (15 ml) was added, and the mixture was stirred at room temperature for 8 hours. The reaction solution was concentrated, the obtained residue was dissolved in methylene chloride (50 ml), triethylamine (1.5 ml) and isobutyryl chloride (0.7 ml) were added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 0.95 g of the target compound. Yield 64% Of the obtained target substance 1 The 1H-NMR is shown below. 1 1H-NMR (CDCl 3 ) δ: 8.10 (1H, s), 7.64 - 7.00 (3H, m), 6.00(1H, m), 5.21(2H, s), 4.22 - 3.57 (4H, m), 4.00 (3H, s), 2.64(3H, s), 2.34 - 2.27(1H,m), 1.10 (6H, d) (Step 3) Synthesis of N-(2-(5-(1-(ethoxyimino)ethyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (Compound No. A-36)

[0265] [Chemical formula]

[0266] N-(2-(5-acetyl-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (0.50 g) was dissolved in chloroform (8 ml) and ethanol (8 ml), and pyridine (0.10 g) and ethoxyamine hydrochloride (0.12 g) were added at room temperature, followed by stirring for 3 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.45 g of the target compound. Yield 82% Of the obtained target substance 1 The 1H-NMR is shown below. 1 1H-NMR (CDCl 3) δ: 7.64 - 7.00 (3H, m), 7.33(1H, s), 6.15(1H, m), 5.13 (2H, s), 4.20 - 3.53 (6H, m), 3.99 (3H, s), 2.34 - 2.27(1H, m), 2.19(3H, s), 1.27(3H, t), 1.10 (6H, d) (Step 4) Synthesis of N-(2-(5-(1-(ethoxyimino)ethyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (Compound No. A-37)

[0267] [Chemical Structure]

[0268] N-(2-(5-(1-(ethoxyimino)ethyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (0.25 g) was dissolved in methanol (4 ml) and tetrahydrofuran (4 ml), and sodium borohydride (20 mg) was added under ice-cooling, followed by stirring for 30 minutes. An aqueous saturated ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain 0.25 g of the target compound. Yield 99% The 1 1H-NMR of the obtained target product is shown below. 1 1H-NMR (CDCl 3) δ: 7.40(1H, s),7.35 - 6.80 (3H, m),5.90 - 5.48 (2H, m), 4.44 - 3.24 (9H, m), 3.85 (3H, s), 2.34 - 2.27(1H, m), 2.14(3H,s), 1.27(3H, t), 1.10 (6H, d) (Project 5) Synthesis of N-(2-(3-(2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxyphenyl)ethyl)-5-(1-(ethoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide

[0269]

Chem.

[0270] Dissolve N-(2-(5-(1-(ethoxyimino)ethyl)-3-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)ethyl)isobutyramide (0.23 g) in tetrahydrofuran (4 ml), add acrylonitrile (0.27 g) and 40% aqueous potassium hydroxide solution (0.3 ml), and stir at room temperature overnight. Add water to the reaction solution, extract with chloroform, and dry over anhydrous sodium sulfate. Distill off the solvent under reduced pressure, and purify the obtained residue by silica gel column chromatography (developing solvent: hexane / ethyl acetate) to obtain 0.12 g of the target compound. Yield 47% Of the obtained target product 1 The 1H-NMR is shown below. 1 1H-NMR (CDCl 3) δ: 7.46(1H, s),7.15-6.83 (3H, m),6.28-5.18 (2H, m), 4.32-3.48 (10H, m), 3.84 (3H, s), 2.64(2H, t), 2.34-2.27(1H,m), 2.16(3H, s), 1.30(3H, t), 1.10 (6H, d)

[0271] Example 3 Synthesis of N-((2S)-1-(3-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((E)-1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (Compound Nos. A-74 and A-75) (Step 1) Synthesis of (E)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione

[0272]

Chemical Structure

[0273] 5-acetylpyrimidine-2,4(1H,3H)-dione (15.4 g) was dissolved in ethanol (200 ml) and chloroform (100 ml), 2-(aminooxy)propane hydrochloride (14.0 g) was added, and the mixture was stirred at 45 °C for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with methylene chloride and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 20.6 g of the target compound. Yield 98% For the obtained target product 1 1H-NMR is shown below. 1 1H-NMR (DMSO-D 6) δ: 11.26 (1H, s), 11.11 (1H, d, J = 5.9Hz), 7.42 (1H, d, J = 5.9 Hz), 4.31-4.25 (1H, m), 1.99 (3H, s), 1.20 (6H, d, J=6.3 Hz). (Step 2) Synthesis of (E)-1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione (Production Intermediate 7)

[0274]

Chemical Structure

[0275] (E)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione (2.11 g) was dissolved in N,N-dimethylformamide (30 ml), potassium carbonate (1.50 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone (2.55 g) were added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the resulting solid was filtered to obtain 3.39 g of the target product. Yield: 90% 1H-NMR of the obtained target product is shown below. 1 1H-NMR 1 1H-NMR (CDCl 3 ) δ: 8.23 (1H, s), 7.67-6.98(3H, m),7.34(1H, s), 5.13(2H, s), 4.35-4.32 (1H, m), 3.98(3H, s), 2.19 (3H, s), 1.25(6H, d, J = 6.3 Hz). (Step 3) (S,E)-N-(1-(3-(2-(5-Fluoro-2-methoxyphenyl)-2-oxoethyl)-5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (Compound No. C-221) Synthesis

[0276] [Chemical Structure]

[0277] (E)-1-(2-(5-Fluoro-2-methoxyphenyl)-2-oxoethyl)-5-(1-(isopropoxyimino)ethyl)pyrimidine-2,4(1H,3H)-dione (0.56 g) was dissolved in tetrahydrofuran (7 ml), and tert-butyl (S)-(1-hydroxypropan-2-yl)carbamate (0.38 g), triphenylphosphine (0.58 g), and bis(2-methoxyethyl) azodicarboxylate (0.52 g) were added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), and the obtained product was dissolved in 1,4-dioxane (7 ml), and 4N hydrogen chloride / 1,4-dioxane solution (7 ml) was added, and the mixture was stirred at room temperature for 4 hours. The reaction solution was concentrated, and the obtained residue was dissolved in methylene chloride (7 ml). Under ice-cooling, triethylamine (3 ml) and isobutanoyl chloride (0.1 ml) were added, and the mixture was stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 0.45 g of the target compound. Yield 60% For the obtained target product 1 1H-NMR is shown below. 1 1H-NMR (CDCl 3) δ: 7.62 - 6.99 (3H, m), 7.30(1H, s), 6.08 - 2.20(8H, m), 3.98 (3H, s), 2.15(3H, s), 1.25 - 1.03 (15H, m) (Step 4) Synthesis of N-((2S)-1-(3-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((E)-1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (Compound Nos. A-74 and A-75)

[0278] [Chemical Formula]

[0279] (S,E)-N-(1-(3-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (0.25 g) was dissolved in methanol (2 ml) and tetrahydrofuran (2 ml), and sodium borohydride (18 mg) was added under ice-cooling, followed by stirring for 20 minutes. An aqueous saturated ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain the target compounds A-74 (0.11 g) and A-75 (0.11 g). The yields were 44% respectively For the obtained target product 1 1H-NMR is shown below. Compound No. A-75: 1 1H-NMR (CDCl 3) δ: 7.38(1H, s),7.36 - 6.79 (3H, m), 5.64 - 4.22(7H, m), 3.84 (3H, s), 3.80 - 3.11(2H, m), 2.25 - 2.16(1H, m), 2.12(3H, s),1.24 - 1.02(15H, m) Compound number A - 74: 1 H - NMR (CDCl 3 ) δ: 7.42(1H, s),7.39 - 6.79 (3H, m), 5.72 - 2.16(10H, m), 3.84 (3H, s), 2.14(3H, s), 1.27 - 1.02(15H, m)

[0280] [Example 4] Synthesis of N - ((2S)-1-(3-(2 - hydroxy - 2-(2-(trifluoromethoxy)phenyl)ethyl)-5-((E)-1-(isopropoxyimino)ethyl)-2,6 - dioxo - 3,6 - dihydropyrimidin - 1(2H)-yl)propan - 2 - yl)isobutyramide (Compound numbers C - 193 and C - 194) (Step 1) Synthesis of (E)-5-(1-(isopropoxyimino)ethyl)-1-(methoxymethyl)pyrimidine - 2,4(1H,3H)-dione

[0281] [Chemical formula]

[0282] (E)-5-(1-(isopropoxyimino)ethyl)pyrimidine - 2,4(1H,3H)-dione (2.50 g) was dissolved in methylene chloride (140 ml), N,O - bis(trimethylsilyl)acetamide (10 ml) was added, and the mixture was stirred at room temperature for 1 hour. Then chloromethyl methyl ether (1.3 ml) was added and the mixture was stirred at room temperature overnight. The reaction solution was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate) to obtain 3.00 g of the target product. The yield was 99%. Of the obtained target product 1 The 1H-NMR is shown below. 1 1H-NMR (CDCl 3 ) δ: 8.32 (1H, s), 7.53 (1H, s), 5.15 (2H, s), 4.40 - 4.34 (1H, m), 3.44 (3H, s), 2.16 (3H, s), 1.27 (6H, d, J = 15.2 Hz). (Step 2) Synthesis of (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-3-(methoxymethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (Production Intermediate 10)

[0283] [Chemical formula]

[0284] (E)-5-(1-(isopropoxyimino)ethyl)-1-(methoxymethyl)pyrimidine-2,4(1H,3H)-dione (2.50 g) was dissolved in tetrahydrofuran (25 ml), and tert-butyl (S)-(1-hydroxypropan-2-yl)carbamate (2.50 g), triphenylphosphine (3.80 g), and bis(2-methoxyethyl) azodicarboxylate (3.40 g) were added, followed by stirring at room temperature for 7 hours. The reaction solution was purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate), and the resulting product was dissolved in 1,4-dioxane (20 ml). A 4N hydrogen chloride / 1,4-dioxane solution (12 ml) was added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated, and the resulting residue was dissolved in methylene chloride (40 ml). Under ice-cooling, triethylamine (3 ml) and isobutanoyl chloride (1.3 ml) were added, and the mixture was stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: chloroform / ethyl acetate) to obtain 2.90 g of the target compound. The yield was 77% The obtained target product 1 The 1H-NMR is shown below. 1 1H-NMR (CDCl 3 ) δ: 7.49 (1H, s), 5.93 (1H, d, J = 8.2 Hz), 5.19 - 5.13 (2H, m), 4.42 - 4.32 (2H, m), 4.15 - 3.87 (2H, m), 3.43 (3H, s), 2.30 - 2.18 (1H, m), 2.14 (3H, s), 1.37 - 0.93 (15H, m). (Step 3) Synthesis of (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (Production Intermediate 9)

[0285] [Chemical Structure Diagram]

[0286] (S,E)-N-(1-(5-(1-(Isopropoxyimino)ethyl)-3-(methoxymethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (0.50 g) was dissolved in methylene chloride (15 ml). Under ice-cooling, a 17% boron tribromide methylene chloride solution (1.5 ml) was added, and the mixture was stirred overnight. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and after extraction with methylene chloride, it was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent: hexane·ethyl acetate) to obtain 0.32 g of the target product. Yield: 72% Of the obtained target product 1 1H-NMR is shown below. 1 1H-NMR (CDCl 3 ) δ: 9.33 (1H, d, J = 6.3 Hz), 7.42 (1H, d, J = 6.3 Hz), 5.94 (1H, d, J = 8.2 Hz), 4.48 - 3.84 (4H, m), 2.25 - 2.21 (1H, m), 2.12 (3H, s), 1.26 - 1.01 (15H, m). (Step 4) Synthesis of (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3-(2-oxo-2-(2-(trifluoromethoxy)phenyl)ethyl)-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (Compound No. C-195)

[0287]

Chemical formula

[0288] (S,E)-N-(1-(5-(1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (0.20 g) was dissolved in N,N-dimethylformamide (3 ml). Under ice-cooling, 2-bromo-1-(2-(trifluoromethoxy)phenyl)ethan-1-one (0.25 g) and potassium carbonate (0.10 g) were added, and the mixture was stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel chromatography (developing solvent: hexane / ethyl acetate) to obtain 0.23 g of the target product. Yield: 72% For the obtained target product 1 1H-NMR is shown below. 1 1H-NMR (CDCl 3 ) δ: 7.98 - 7.36 (4H, m), 7.33 (1H, s), 6.07 - 3.90 (7H, m), 2.28 - 2.21 (1H, m), 2.17 (3H, s), 1.26 - 1.05 (15H, m). (Step 5) Synthesis of N-((2S)-1-(3-(2-hydroxy-2-(2-(trifluoromethoxy)phenyl)ethyl)-5-((E)-1-(isopropoxyimino)ethyl)-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (Compound Nos. C-193 and C-194)

[0289]

Chemical formula

[0290] (S,E)-N-(1-(5-(1-(Isopropoxyimino)ethyl)-2,6-dioxo-3-(2-oxo-2-(2-(trifluoromethoxy)phenyl)ethyl)-3,6-dihydropyrimidin-1(2H)-yl)propan-2-yl)isobutyramide (0.19 g) was dissolved in methanol (2 ml) and tetrahydrofuran (2 ml). Under ice-cooling, sodium borohydride (15 mg) was added and the mixture was stirred for 40 minutes. An aqueous saturated ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain the target compounds C-193 (0.90 g) and C-194 (0.90 g). The yields were 47% respectively. Of the obtained target products 1 1H-NMR is shown below. Compound No. C-194: 1 1H-NMR (CDCl 3 ) δ: 7.76 - 7.27 (4H, m), 7.41 (1H, s), 5.75 - 5.43 (3H, m), 4.77 - 4.24 (4H, m), 3.81 - 3.13 (2H, m), 2.21 - 2.18 (1H, m), 2.12 (3H, s), 1.28 - 1.00 (15H, m). Compound No. C-193: 1 1H-NMR (CDCl 3 ) δ: 7.84 - 7.35 (4H, m), 7.42 (1H, s), 5.64 - 3.74 (9H, m), 2.25 - 2.18 (1H, m), 2.14 (3H, s), 1.28 - 1.01 (15H, m).

[0291] Some of the compounds of the present invention produced in the same manner as in the above examples are shown in Table 2. In the table, the melting point (m.p.) is also shown as the physical property of each compound.

[0292]

Table 2

[0293] Furthermore, a part of the compounds of the present invention produced in the same manner as in the above examples is shown in Table 3. In the table, the melting point (m.p.) is also shown as the physical property of each compound. Also, in the case of stereoisomers, it is indicated in the special notes.

Table 3

[0294] Furthermore, a part of the compounds of the present invention produced in the same manner as in the above examples is shown in Table 4. In the table, the melting point (m.p.) is also shown as the physical property of each compound. Also, in the case of stereoisomers, it is indicated in the special notes.

Table 4

[0295] Among the compounds described in Tables 2 to 4, for the compounds having the properties of amorphous or viscous oil, in Table 5 below, their 1 1H-NMR data are shown. [Table 5] TIFF2025081445000059.tif249170TIFF2025081445000060.tif178113TIFF2025081445000061.tif121170

[0296] Furthermore, a part of the compounds of the present invention produced by the same method as in the above examples is shown in Table 6. In the table, the melting point (m.p.) is also shown as the physical property of each compound. Also, in the case of stereoisomers, it is indicated in the special remarks. [Table 6] TIFF2025081445000063.tif226170TIFF2025081445000064.tif220170TIFF2025081445000065.tif220170TIFF2025081445000066.tif220170TIFF2025081445000067.tif222170TIFF2025081445000068.tif222170TIFF2025081445000069.tif222170TIFF2025081445000070.tif222170TIFF2025081445000071.tif223170TIFF2025081445000072.tif222170TIFF2025081445000073.tif222170TIFF2025081445000074.tif222170TIFF2025081445000075.tif223170TIFF2025081445000076.tif222170TIFF2025081445000077.tif222170TIFF2025081445000078.tif222170TIFF2025081445000079.tif222170TIFF2025081445000080.tif222170TIFF2025081445000081.tif222170TIFF2025081445000082.tif222170TIFF2025081445000083.tif222170TIFF2025081445000084.tif222170TIFF2025081445000085.tif222170TIFF2025081445000086.tif222170TIFF2025081445000087.tif222170TIFF2025081445000088.tif222170TIFF2025081445000089.tif222170TIFF2025081445000090.tif222170TIFF2025081445000091.tif222170TIFF2025081445000092.tif222170TIFF2025081445000093.tif222170TIFF2025081445000094.tif222170TIFF2025081445000095.tif222170TIFF2025081445000096.tif222170TIFF2025081445000097.tif222170TIFF2025081445000098.tif222170TIFF2025081445000099.tif222170TIFF2025081445000100.tif222170TIFF2025081445000101.tif222170TIFF2025081445000102.tif223170TIFF2025081445000103.tif222170TIFF2025081445000104.tif222170TIFF2025081445000105.tif222170TIFF2025081445000106.tif222170TIFF2025081445000107.tif222170TIFF2025081445000108.tif222170TIFF2025081445000109.tif222170TIFF2025081445000110.tif141170.

[0297] Furthermore, a part of the compounds of the present invention produced in the same manner as in the above examples is shown in Table 7. In the table, the melting point (m.p.) is also shown as the physical property of each compound. Also, in the case of stereoisomers, they are indicated as noted.

Table 7

[0298] Among the compounds described in Tables 6 and 7, for the compounds having the properties of amorphous or viscous oil, in Table 8 below, their 1 1H-NMR data are shown.

Table 8

[0299] 〔Biological test〕 The following test examples show that the dihydropyrimidine compound of the present invention is useful as an active ingredient of a fungicide for agricultural and horticultural use. The dihydropyrimidine compounds used in the tests are shown in Tables 9 and 10 below for each test. The compound numbers in Table 9 correspond to the compound numbers in Tables 2 to 4. The compound numbers in Table 10 correspond to the compound numbers in Tables 6 and 7.

[0300]

Table 9

[0301]

Table 10

[0302] (Preparation of test emulsion) 5 parts by weight of the dihydropyrimidine 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 emulsion (I) containing 5% of the active ingredient.

[0303] The control value was calculated by the following formula.

[0304] [Equation 1] Control value (%) = 100 - {lesion area ratio in the treated plot / lesion area ratio in the untreated plot} × 100

[0305] (Test Example 1) Apple scab control test Water was added to emulsion (I) so that the concentration of the dihydropyrimidine compound became 125 ppm and dissolved to obtain a chemical solution. Subsequently, the chemical solution was sprayed on apple seedlings (cultivar "Orin", 3 - 4 leaf stage) cultivated in seedling pots. After air drying, conidia of Venturia inaequalis were inoculated (treated plot). As a control, apple seedlings not sprayed with the chemical solution were similarly inoculated (untreated plot). They were left in a humidity chamber at 20°C with light and dark repeated every 12 hours. Two weeks after inoculation, the leaves of apple seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

[0306] For the dihydropyrimidine compounds described in Tables 9 and 10, an apple scab control test was conducted. All of the compounds showed a control value of 75% or more.

[0307] (Test Example 2) Wheat powdery mildew control test Water was added to Emulsion (I) to dissolve the dihydropyrimidine compound to a concentration of 125 ppm, and a chemical solution was obtained. Subsequently, the chemical solution was sprayed onto wheat seedlings (cultivar "Chihoku", 1-2 leaf stage) cultivated in pots for raising seedlings. After air drying, conidia of Erysiphe graminis f.sp. tritici were sprinkled and inoculated (treatment group). As a control, wheat seedlings not sprayed with the chemical solution were inoculated in the same manner as above (non-treatment group). They were left standing in a greenhouse at 20°C. Six days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

[0308] For the dihydropyrimidine compounds described in Tables 9 and 10, a wheat powdery mildew control test was conducted. All of the compounds showed a control value of 75% or more.

[0309] (Test Example 3) Wheat leaf rust control test Water was added to Emulsion (I) to dissolve the dihydropyrimidine compound to a concentration of 125 ppm, and a chemical solution was obtained. Subsequently, the chemical solution was sprayed onto wheat seedlings (cultivar "Norin 61", 1-2 leaf stage) cultivated in pots for raising seedlings. After air drying, uredospores of Puccinia recondita were sprinkled onto the wheat seedlings sprayed with the chemical solution and inoculated (treatment group). As a control, wheat seedlings not sprayed with the chemical solution were inoculated in the same manner as above (non-treatment group). They were left standing in a greenhouse at 20°C. Twelve days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

[0310] A wheat rust control test was conducted on the dihydropyrimidine compounds described in Tables 9 and 10. All of the compounds showed a control value of 75% or more.

[0311] (Test Example 4) Cucumber gray mold control test Water was added to Emulsion (I) so that the concentration of the dihydropyrimidine compound became 125 ppm and dissolved to obtain a chemical solution. Subsequently, the chemical solution was sprayed onto cucumber seedlings (cultivar "Jicho" line, cotyledon stage) cultivated in pots for raising seedlings. After air drying, a suspension of conidia of Botrytis cinerea was drop-inoculated (treatment group). As a control, cucumber seedlings not sprayed with the chemical solution were drop-inoculated in the same manner as above (non-treatment group). They were left standing in a humid chamber at 20°C. Four days after inoculation, the leaves of the cucumber seedlings were visually observed to determine the lesion area ratio and calculate the control value.

[0312] A cucumber gray mold control test was conducted on the dihydropyrimidine compounds described in Tables 9 and 10. All of the compounds showed a control value of 75% or more.

[0313] (Test Example 5) Wheat powdery mildew seed treatment test For wheat seeds (cultivar "Chihoku"), Emulsion (I) was used for seed treatment so that (weight of dihydropyrimidine compound) / (weight of seeds) was 100 g / 100 kg. These seeds were sown in pots and, 8 to 10 days later, conidia of Erysiphe graminis f.sp.tritici were sprinkled and inoculated (treatment group). As a control, wheat seedlings not treated with the chemical were inoculated in the same manner as above (non-treatment group). They were left standing in a greenhouse at 20°C. Seven days after inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio and calculate the control value.

[0314] A wheat powdery mildew seed treatment test was conducted on the dihydropyrimidine compounds described in Table 11. All of the compounds showed a control value of 75% or more.

[0315]

Table 11

[0316] (Test Example 6) Wheat Powdery Mildew Soil Irrigation Treatment Test To a pot (5.5 cm × 5.5 cm) sown with wheat seeds (cultivar "Chihoku"), 10 mL of a chemical solution in which water was added to emulsion (I) to make the concentration of the dihydropyrimidine compound 100 ppm was irrigated, and after 8 to 10 days, conidia of the wheat powdery mildew fungus (Erysiphe graminis f.sp.tritici) were sprinkled and inoculated (treatment group). As a control, wheat seedlings not treated with the chemical were inoculated in the same manner as above (non-treatment group). They were left standing in a greenhouse at 20°C. Seven days after inoculation, the leaves of the wheat seedlings were visually observed to determine the lesion area ratio and calculate the control value.

[0317] A wheat powdery mildew soil irrigation treatment test was conducted on the dihydropyrimidine compounds described in Table 12. All of the compounds showed a control value of 75% or more.

[0318]

Table 12

[0319] The following test examples show that the dihydropyrimidine compounds of the present invention are useful as active ingredients of nematicides. (Test Example 7) Efficacy against Sweet Potato Stem Nematode To a 96-well microplate, 160 μL of a suspension containing about 50 second-stage larvae (L2) of the sweet potato stem nematode per 0.16 mL was poured into each well, and then 40 μL of a chemical solution in which water was added to emulsion (I) to make the concentration of the dihydropyrimidine compound 125 ppm was poured into each well. The plate was left standing at 20°C for 4 days. Thereafter, viability determination was performed and the nematode kill rate was calculated. Individuals that did not show movement for 10 seconds were determined to be dead. The test was conducted in 2 replicates.

[0320] For the compounds of Compound Nos. A-28, A-64, C-92, and C-145, an efficacy test against the sweet potato nematode was conducted. The nematode killing rate of each compound against the sweet potato nematode was 60% or more.

[0321] The following test examples show that the dihydropyrimidine compound of the present invention is useful as an active ingredient of an antifungal agent for medical and animal use. (Test Example 8) Antibacterial test against Fusarium graminearum Water was added to the emulsion (I) so that the concentration of the dihydropyrimidine compound became 125 ppm and dissolved to obtain a drug solution. Spores of Fusarium graminearum were added to a potato sucrose yeast extract medium and dispersed. Further, the above drug solution was added and mixed so that the concentration of the dihydropyrimidine compound in the culture solution became 15.6 ppm. These were dispensed onto a 96-well microplate and cultured in the dark at 20 °C for 4 days. After culturing, the turbidity at a wavelength of 405 nm was measured with a microplate reader, and the growth inhibition rate (%) of Fusarium graminearum was determined compared with the case of no treatment.

[0322] An antibacterial test against Fusarium graminearum was conducted for the dihydropyrimidine compounds described in Table 13. Each compound showed an excellent growth inhibition rate of 50% or more.

[0323]

Table 13

[0324] (Test Example 9) Antibacterial test against Aspergillus niger Spores of Aspergillus niger were added to Vogel medium and dispersed, and a dihydropyrimidine compound dissolved in dimethyl sulfoxide was added and mixed to a concentration of 25 ppm. These were dispensed onto a 96-well microplate and cultured in the dark at 25 °C for 4 days. After culturing, the turbidity at a wavelength of 405 nm was measured with a microplate reader, and the growth inhibition rate (%) of Aspergillus niger was determined compared to the untreated case.

[0325] An antibacterial test against Aspergillus niger was conducted for the dihydropyrimidine compounds described in Table 14. All of the compounds showed excellent growth inhibition rates of 50% or more.

[0326]

Table 14

Industrial Applicability

[0327] Since randomly selected ones from the dihydropyrimidine compounds of the present invention have the above-described effects, the dihydropyrimidine compounds of the present invention have bactericidal / antibacterial effects and nematicidal effects, including compounds that could not be fully exemplified, do not cause phytotoxicity to plants, and are compounds with low toxicity to humans, livestock, and fish and little impact on the environment. They are useful as agricultural chemicals, nematicides, and antifungal agents for medical and animal use.

Claims

1. A compound represented by formula (III) or a salt thereof: 【Chemistry 1】 [In formula (III), X １ represents a hydrogen atom; X ２ is R １ O-N=CR ６ - represents a group represented by; R １ represents a substituted or unsubstituted C1-6 alkyl group, R ６ is a hydrogen atom or represents a substituted or unsubstituted C1-6 alkyl group; A represents a substituted or unsubstituted C1-6 alkylene group; The substituent on the C1-6 alkylene group in A is Hydroxyl group, Substituted or unsubstituted C1-6 alkoxy group an oxo group (O=), or R ａ１ A divalent group represented by O-N=, R ａ１ represents a substituted or unsubstituted C1-6 alkyl group; Q represents a substituted or unsubstituted C6-10 aryl group.

2. A compound represented by formula (IV) or a salt thereof: 【Chemistry 2】 [In formula (IV), X １ represents a hydrogen atom; X ２ is R １ O-N=CR ６ represents a group represented by -, R １ represents a substituted or unsubstituted C1-6 alkyl group, R ６ is a hydrogen atom or represents a substituted or unsubstituted C1-6 alkyl group; X ３ is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or represents a substituted or unsubstituted 4- to 6-membered heterocyclyl group; X ３ The substituents on the linear C1-6 alkyl group, C3-6 cycloalkyl group, C6-10 aryl group and 4- to 6-membered heterocyclyl group in a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, Hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 3- to 10-membered heterocyclyl group, Cyano group, R ａ a group represented by -CO-, 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 ａ -CO-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-CO-CO-NR ｅ A group represented by -, R ｃ R ｄ N-CS-NR ｅ A group represented by -, R ｂ SO ２ -NR ｅ A group represented by -, R ａ O-N=CR ｆ -, and R ｈ R ｉ A group represented by C=N-O- One or more substituents selected from the group consisting of: R ａ are each independently 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 represents a substituted or unsubstituted 3- to 10-membered heterocyclyl group; R ｂ are each independently a substituted or unsubstituted C1-6 alkyl group, or represents a substituted or unsubstituted C3-6 cycloalkyl group, R ｃ are each independently Hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or represents a substituted or unsubstituted C6-10 aryl group, R ｄ are each independently Hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or represents a substituted or unsubstituted C1-6 alkoxy group, Here, R ｃ and R ｄ may be taken together to form a divalent organic group, R ｅ are each independently Hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or represents a substituted or unsubstituted C1-6 alkoxy group, R ｆ teeth, a hydrogen atom, or represents an amino group, R ｈ are each independently represents a substituted or unsubstituted C1-6 alkyl group, R ｉ are each independently represents a substituted or unsubstituted C1-6 alkyl group, Here, R ｈ and R ｉ may be taken together to form a divalent organic group; X ４ represents a hydrogen atom or a C1-6 alkoxymethyl group.

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