Nicotinamide derivative and agricultural and horticultural plant disease control agent

Abstract

[Problem] To provide an excellent agricultural and horticultural plant disease control agent. [Solution] Provided is a nicotinamide derivative, or its salt, represented by general formula [I] [In the formula, Q denotes -NRaRb or the like, W denotes an oxygen atom or the like, Y denotes an oxygen atom or the like, A1 denotes an oxygen atom or the like, A2 denotes -CH- or a nitrogen atom, R1 denotes a hydrogen atom or the like, R2 and R3 each independently denote a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, or the like, L denotes L-1, L-2 or L-3, R5 denotes a C1-C6 alkyl group or the like, R6 denotes a hydrogen atom or the like, R7 denotes a hydrogen atom or the like, R8 denotes a hydrogen atom, a halogen atom, a C1-C6 alkoxy group, or the like, R9 denotes a hydrogen atom or the like, Rx and Ry each independently denote a hydrogen atom, a halogen atom, or the like, Rz denotes a hydrogen atom or the like, and Ra and Rb each independently denote a hydrogen atom, a C1-C6 alkyl group, or the like], or a salt thereof. Also provided is an agricultural and horticultural plant disease control agent that contains this nicotinamide derivative, or its salt, as an active ingredient.　

Description

Nicotinamide derivatives and agricultural and horticultural plant disease control agents

[0001] The present invention relates to a novel nicotinamide derivative or a salt thereof, and an agricultural and horticultural plant disease control agent containing a nicotinamide derivative or a salt thereof as an active ingredient.

[0002] Patent Document 1 describes nicotinamide derivatives as compounds useful for angiogenesis-related diseases, but does not describe their plant disease control activity. Furthermore, the substituent at the 2-position of the nicotine moiety is limited to a 4- to 6-membered heterocyclylamino group, a substituted arylamino group, and a 9- to 14-membered bicyclic or tricyclic heterocyclylamino group.

[0003] Patent Document 2 describes nicotinamide derivatives as nitric oxide production promoters, but does not describe their plant disease control activity.

[0004] International Publication No. 2002 / 068406 Japanese Patent Application Laid-Open No. 2007-186435

[0005] BACKGROUND ART In the cultivation of useful crops, a large number of plant disease control agents are used to combat plant diseases caused by pathogenic fungi.

[0006] However, conventional plant disease control agents have insufficient control efficacy against plant diseases caused by pathogenic fungi, or their use is sometimes restricted due to the emergence of pathogenic fungi that are resistant to the agents and the resulting plant diseases. Furthermore, they do not necessarily have satisfactory performance in terms of causing phytotoxicity or contamination of plants, or toxicity to humans, livestock, and fish, and their impact on the environment.

[0007] Therefore, there is a strong demand for the development of a plant disease control agent which has fewer of these drawbacks and can be used safely.

[0008] As a result of extensive research, the present inventors have found that a drug containing, as an active ingredient, a nicotinamide derivative represented by the following formula [I] or a salt thereof has a high control effect against plant diseases caused by pathogenic fungi in the cultivation of useful crops, and have thus completed the present invention.

[0009] That is, the gist of the present invention is as follows: (1) General formula [I]

[0010] wherein Q is —NR ａ R ｂ or a nitro group, W represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), A １ represents an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), —CH ２ - or -NR ｃ - indicates A ２ represents —CH— or a nitrogen atom, R １ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ haloalkyl group, or C １ ~C ６ represents an alkoxy group, R ２ and R ３ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C１ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, cyano group, formyl group, carboxyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ３ ~C ８ a cycloalkylaminocarbonyl group (the cycloalkyl group may be substituted with a substituent selected from substituent group β, and the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), and further, R ２and R ３ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 5- or 6-membered ring together with 0 to 1 atom or atomic group selected from, and the 5- or 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group; ４ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, formyl group, C １ ~C ６ Alkylcarbonyl group, or C １ ~C ６ represents an alkoxycarbonyl group, L represents L-1, L-2, or L-3, and R ５ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C ６ ~C １２an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a cyano C １ ~C ６ Alkyl group, or C ６ ~C １２ Aryl C １ ~C ６ R represents an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α); ６ represents a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ haloalkyl group, or C １ ~C ６ represents an alkoxy group, R ７ represents a hydrogen atom, a halogen atom, a hydroxy group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), R ８ represents a hydrogen atom, a halogen atom, a hydroxy group, a mercapto group, a cyano group, a nitro group, -CR ｄ R ｅ R ｆ , -OR ｈ , -NR ｉ R ｋ , methyl group, C ３~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkenyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, tri(C １ ~C ６ Alkyl)silyl C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C ３ ~C ８ a cycloalkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylthio group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylsulfinyl group, C １ ~C６ Alkoxy C １ ~C ６ Alkyl sulfonyl group, cyanothio group, C １ ~C ６ Alkylcarbonylthio group, aminosulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylthio group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfinyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２ an arylsulfonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylthio group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfinyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfonyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylthio group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylsulfinyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylsulfonyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a formyl group, a carboxyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C１ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ３ ~C ８ a cycloalkylaminocarbonyl group (the cycloalkyl group may be substituted with a substituent selected from substituent group β, and the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α, and the amino group may be substituted with a substituent selected from Substituent Group γ), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), —C(═NR ｍ ) R ｎ group, or —C(R ｏ ) = CR ｐ (R ｓ ) group, R ９ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２R represents an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), ｘ and R ｙ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ represents an alkyl group, and further represents R ｘ and R ｙ may be taken together to form an oxo group, R ｚ is a hydrogen atom, a halogen atom, or C １ ~C ６ represents an alkyl group, R ａ and R ｂ are each independently a hydrogen atom, a hydroxy group, an amino group, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), a formyl group, C１ ~C ６ Alkylcarbonyl group, C １ ~C ６ Haloalkylcarbonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), and R ａ and R ｂ are combined to form (=CH)-(C １ ~C ６ alkyl group), (=CH)-(C ６ ~C １２ aryl group) (the aryl group may be substituted with one or more substituents selected from Substituent Group α), or (═CH)—N(C １ ~C ６ alkyl group) ２ and further, R ａ and R ｂ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a nitrogen-containing 4- to 6-membered ring together with 0 to 1 atom or atomic group selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group; ｃ is a hydrogen atom, C １ ~C ６ Alkyl group, or C １ ~C ６ represents an alkylcarbonyl group, R ｄ , Rｅ are each independently a hydrogen atom, a halogen atom, a hydroxy group, a mercapto group, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, or tri(C １ ~C ６ represents an alkyl)silyloxy group, or R ｄ and R ｅ Let's get together = CH ２ and further, R ｄ and R ｅ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 3- to 6-membered ring together with 0 to 2 atoms or atomic groups selected from, and the 3- to 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group; ｆ represents a halogen atom, a hydroxy group, a mercapto group, an amino group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryloxy C １ ~C ６ alkyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyloxy C １ ~C ６ alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), 5- to 12-membered heteroaryloxy C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a mercapto C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １~C ６ Alkyl group, C ３ ~C ８ Cycloalkylthio C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminosulfonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a cyanothio C １ ~C ６ Alkyl group, amino C １ ~C ６ Alkyl group, C １ ~C ６ Alkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ Cycloalkylamino C １ ~C ６an alkyl group (the cycloalkyl group may be substituted with a substituent selected from substituent group β, and the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ Haloalkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylcarbonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkoxycarbonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkyl sulfonyl amino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Haloalkylsulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), an aminosulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ); １ ~C ６ Alkylaminosulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a cyano C １ ~C ６ Alkyl group, formyl C １ ~C ６ Alkyl group, carboxyl group １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl C １ ~C ６Alkyl group, C １ ~C ６ Alkoxycarbonyl C １ ~C ６ Alkyl group, aminocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Arylaminocarbonyl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), a hydroxyaminocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxyaminocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Arylcarbonyl C １ ~C ６ an alkyl group, (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroarylcarbonyl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclylcarbonyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), an aminothiocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminothiocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), -(C１ ~C ６ alkyl)-C(=NR ｍ ) R ｎ , C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkoxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６ an alkoxy group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkoxy group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkoxy group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６Alkylcarbonyloxy group, C ３ ~C ８ a cycloalkylcarbonyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), an aminocarbonyloxy group, C ６ ~C １２ an aryloxy group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryloxy group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyloxy group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C ３ ~C ８ a cycloalkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkyl C １ ~C ６an alkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylthio group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl group, cyanothio group, C １ ~C ６ Alkylcarbonylthio group, aminosulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylthio group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfinyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２ an arylsulfonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylthio group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfinyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfonyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), C １ ~C ６an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ a cycloalkylamino group (the cycloalkyl group may be substituted with a substituent selected from substituent group β, and the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ haloalkylamino group (the amino group may be substituted with a substituent selected from substituent group γ), aminocarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ an alkylaminocarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ an alkoxycarbonylamino group (the amino group may be substituted with a substituent selected from Substituent group α), C １ ~C ６ an alkylsulfonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ haloalkylsulfonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), aminosulfonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ alkylaminosulfonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), 5- to 12-membered heteroarylamino group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), formyl group, carboxyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C ６ ~C １２ an aryloxycarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryloxycarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), an aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a hydroxyaminocarbonyl group, C １ ~C ６ an alkoxyaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ arylaminocarbonyl groups (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), 5- to 12-membered heteroarylaminocarbonyl groups (the heteroaryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), 3- to 6-membered heterocyclylaminocarbonyl groups (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), aminothiocarbonyl groups, C １ ~C ６ an alkylaminothiocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylcarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroarylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), or —C(═NR ｍ ) R ｎ represents a group, R ｈ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryloxy C １ ~C ６ alkyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), 5- to 12-membered heteroaryloxy C １ ~C ６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyloxy C １ ~C ６an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a mercapto C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkylthio C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), formyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), —N═CH—(C １ ~C ６ alkyl group), or -N=C(C １ ~C ６ alkyl group) ２ indicates, R ｉ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a cyano C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl C １ ~C ６ R represents an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α); ｋ represents a hydrogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ alkyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), formyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylcarbonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, cyano C １ ~C ６ Alkylcarbonyl group, C ６ ~C １２ Aryl C １ ~C ６alkylcarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), 5- to 12-membered heteroaryl C １ ~C ６ alkylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylcarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroarylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), and further, R ｉ and R ｋ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a nitrogen-containing 4- to 6-membered ring together with 0 to 1 atom or atomic group selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ R may be substituted by one or more chemically acceptable substituents selected from an alkylcarbonylamino group (the amino group may be substituted by a substituent selected from substituent group γ) or an oxo group; ｍ represents a hydroxy group, an amino group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), or C １ ~C ６ represents an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), R ｎ represents a hydrogen atom, a halogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), R ｏ is a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), R ｐ represents a hydrogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C１ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ an alkoxy group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ an alkoxycarbonyl group, or C １ ~C ６ represents an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), R ｓ is a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ an alkoxycarbonyl group, or C １ ~C ６ represents an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), and further represents R ｐ and R ｓ may be bonded to each other to form a 5- or 6-membered ring together with 0 to 2 atoms or atomic groups selected from carbon atoms, oxygen atoms, and sulfur atoms (the sulfur atoms may be oxidized with 1 or 2 oxygen atoms), and the 5- or 6-membered ring is C１ ~C ６ Alkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group; ｕ is a hydrogen atom or C １ ~C ６ The substituent group α represents a halogen atom, a hydroxy group, a mercapto group, an amino group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a halocycloalkyl group (the halocycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６Alkoxy group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ may be substituted with one or more substituents selected from an alkoxy group and a cyano group), C ２ ~C ６ Alkenyloxy group, C ２ ~C ６ Alkynyloxy group, tri(C １ ~C ６ alkyl)silyloxy group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group is not a halogen atom, C １ ~C ６Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ alkylamino group (the amino group may be substituted with one or more substituents selected from the substituent group γ), cyano group), 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ), a cyano group), an oxo group, or —C(═NR ｍ ) R ｎ The substituent group β represents a halogen atom, a hydroxy group, an amino group, a cyano group, a C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C １ ~C ６ haloalkyl groups), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C１ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group is not a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ alkylamino group (the amino group may be substituted with one or more substituents selected from the substituent group γ), cyano group), 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ) or a cyano group), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with a substituent selected from the substituent group γ) and a cyano group), and the substituent group γ is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C１ ~C ６ haloalkyl groups), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ haloalkylcarbonyl group, or C １ ~C ６ 2. An agricultural and horticultural plant disease control agent comprising, as an active ingredient, a nicotinamide derivative represented by the formula (I): wherein R represents an alkoxycarbonyl group, or a salt thereof.

[0011] (2) General formula [I]

[0012] wherein Q is —NR ａ R ｂ or a nitro group, W represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), A １ represents an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), —CH ２ - or -NR ｃ - indicates A ２ represents —CH— or a nitrogen atom, R １ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ haloalkyl group, or C １ ~C ６ represents an alkoxy group, R ２ and R ３are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, cyano group, formyl group, carboxyl group, C １ ~C ６Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ３ ~C ８ a cycloalkylaminocarbonyl group (the cycloalkyl group may be substituted with a substituent selected from substituent group β, and the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), and further, R ２ and R ３ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 5- or 6-membered ring together with 0 to 1 atom or atomic group selected from, and the 5- or 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group; ４ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, formyl group, C １ ~C ６ Alkylcarbonyl group, or C１ ~C ６ represents an alkoxycarbonyl group, L represents L-1, L-2, or L-3, and R ５ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a cyano C １ ~C ６ Alkyl group, or C ６ ~C １２ Aryl C １ ~C ６ R represents an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α); ６ represents a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ haloalkyl group, methoxy group, or C ３ ~C ６ represents an alkoxy group, R ７ represents a hydrogen atom, a halogen atom, a hydroxy group, C １ ~C ６ Alkyl group, C ３ ~C ８a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), R ８ represents a hydroxy group, a mercapto group, a cyano group, -CR ｄ R ｅ R ｆ , -OR ｈ , -NR ｉ R ｋ , C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkenyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, tri(C １ ~C ６ Alkyl)silyl C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C ３ ~C ８a cycloalkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylthio group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl group, cyanothio group, C １ ~C ６ Alkylcarbonylthio group, aminosulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylthio group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfinyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２an arylsulfonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylthio group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfinyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfonyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylthio group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylsulfinyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylsulfonyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a formyl group, a carboxyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C ３ ~C ８ a cycloalkylaminocarbonyl group (the cycloalkyl group may be substituted with a substituent selected from substituent group β, and the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), —C(═NR ｍ ) R ｎ group, or —C(R ｏ ) = CR ｐ (R ｓ ) group, R ９ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ R represents an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), ｘ and R ｙ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ represents an alkyl group, and further represents R ｘ and R ｙ may be taken together to form an oxo group, R ｚ is a hydrogen atom, a halogen atom, or C １ ~C ６ represents an alkyl group, R ａ represents a hydrogen atom, a hydroxy group, an amino group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a hydroxy C １ ~C ６ Alkyl group, C１ ~C ６ Alkoxy C １ ~C ６ alkyl group, 5- to 12-membered heteroaryl C １ ~C ６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), a formyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Haloalkylcarbonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), R ｂ represents a hydrogen atom, and R ａ and R ｂ are together (=CH)-C １ ~C ６ Alkyl group, (=CH)-C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), or ═CH—N(C １ ~C ６ alkyl group) ２ may form R ｃ is a hydrogen atom, C １ ~C６ Alkyl group, or C １ ~C ６ represents an alkylcarbonyl group, R ｄ , R ｅ are each independently a hydrogen atom, a halogen atom, a hydroxy group, a mercapto group, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, or tri(C １ ~C ６ represents an alkyl)silyloxy group, or R ｄ and R ｅ Let's get together = CH ２ and further, R ｄ and R ｅ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 3- to 6-membered ring together with 0 to 2 atoms or atomic groups selected from, and the 3- to 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group; ｆ represents a chlorine atom, a bromine atom, an iodine atom, a hydroxy group, a mercapto group, an amino group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ３ ~C ８a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryloxy C １ ~C ６ alkyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyloxy C １ ~C ６ alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), 5- to 12-membered heteroaryloxy C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a mercapto C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C１ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkylthio C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminosulfonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a cyanothio C １ ~C ６ Alkyl group, amino C １ ~C ６ Alkyl group, C １ ~C ６ Alkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ Cycloalkylamino C１ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from substituent group β, and the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ Haloalkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylcarbonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkoxycarbonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkyl sulfonyl amino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Haloalkylsulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), an aminosulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ); C １ ~C ６ Alkylaminosulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a cyano C １ ~C ６ Alkyl group, formyl C １ ~C ６ Alkyl group, carboxyl group １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl C１ ~C ６ Alkyl group, C １ ~C ６ Alkoxycarbonyl C １ ~C ６ Alkyl group, aminocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Arylaminocarbonyl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), a hydroxyaminocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxyaminocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Arylcarbonyl C １ ~C ６ an alkyl group, (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroarylcarbonyl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclylcarbonyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), an aminothiocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminothiocarbonyl C １ ~C ６an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), -(C １ ~C ６ alkyl)-C(=NR ｍ ) R ｎ , C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkoxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６ an alkoxy group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkoxy group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyl C １ ~C ６an alkoxy group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylcarbonyloxy group, C ３ ~C ８ a cycloalkylcarbonyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), an aminocarbonyloxy group, C ６ ~C １２ an aryloxy group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryloxy group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyloxy group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C ３ ~C ８ a cycloalkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８Cycloalkyl C １ ~C ６ an alkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylthio group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl group, cyanothio group, C １ ~C ６ Alkylcarbonylthio group, aminosulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylthio group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfinyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２ an arylsulfonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylthio group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfinyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfonyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), C １ ~C ６an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ a cycloalkylamino group (the cycloalkyl group may be substituted with a substituent selected from substituent group β, and the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ haloalkylamino group (the amino group may be substituted with a substituent selected from substituent group γ), aminocarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ an alkylaminocarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ an alkoxycarbonylamino group (the amino group may be substituted with a substituent selected from Substituent group α), C １ ~C ６ an alkylsulfonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ haloalkylsulfonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), aminosulfonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ alkylaminosulfonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), 5- to 12-membered heteroarylamino group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), formyl group, carboxyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C ６ ~C １２ an aryloxycarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryloxycarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), an aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a hydroxyaminocarbonyl group, C １ ~C ６ an alkoxyaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ arylaminocarbonyl groups (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), 5- to 12-membered heteroarylaminocarbonyl groups (the heteroaryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), 3- to 6-membered heterocyclylaminocarbonyl groups (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), aminothiocarbonyl groups, C １ ~C ６ an alkylaminothiocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylcarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroarylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), or —C(═NR ｍ ) R ｎ represents a group, R ｈ is a hydrogen atom, C ２ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryloxy C １ ~C ６ alkyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), 5- to 12-membered heteroaryloxy C １ ~C ６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyloxy C １ ~C ６an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a mercapto C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkylthio C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C６ alkyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), formyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), —N═CH—(C １ ~C ６ alkyl group), or -N=C(C １ ~C ６ alkyl group) ２ indicates, R ｉ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a cyano C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl C １ ~C ６ R represents an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α); ｋ represents a hydrogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ alkyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), formyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylcarbonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, cyano C １ ~C ６ Alkylcarbonyl group, C ６ ~C １２ Aryl C １ ~C ６alkylcarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), 5- to 12-membered heteroaryl C １ ~C ６ alkylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an arylcarbonyl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroarylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), and further, R ｉ and R ｋ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a nitrogen-containing 4- to 6-membered ring together with 0 to 1 atom or atomic group selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ R may be substituted by one or more chemically acceptable substituents selected from an alkylcarbonylamino group (the amino group may be substituted by a substituent selected from substituent group γ) or an oxo group; ｍ represents a hydroxy group, an amino group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), or C １ ~C ６ represents an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), R ｎ represents a hydrogen atom, a halogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), R ｏ is a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), R ｐ represents a hydrogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C１ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ an alkoxy group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ an alkoxycarbonyl group, or C １ ~C ６ represents an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), R ｓ is a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ an alkoxycarbonyl group, or C １ ~C ６ represents an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), and further represents R ｐ and R ｓ may be bonded to each other to form a 5- or 6-membered ring together with 0 to 2 atoms or atomic groups selected from carbon atoms, oxygen atoms, and sulfur atoms (the sulfur atoms may be oxidized with 1 or 2 oxygen atoms), and the 5- or 6-membered ring is C１ ~C ６ Alkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group; ｕ is a hydrogen atom or C １ ~C ６ The substituent group α represents a halogen atom, a hydroxy group, a mercapto group, an amino group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a halocycloalkyl group (the halocycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６Alkoxy group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ may be substituted with one or more substituents selected from an alkoxy group and a cyano group), C ２ ~C ６ Alkenyloxy group, C ２ ~C ６ Alkynyloxy group, tri(C １ ~C ６ alkyl)silyloxy group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group is not a halogen atom, C １ ~C ６Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ alkylamino group (the amino group may be substituted with one or more substituents selected from the substituent group γ), cyano group), 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ) and a cyano group), an oxo group, or —C(═NR ｍ ) R ｎ The substituent group β represents a halogen atom, a hydroxy group, an amino group, a cyano group, a C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C １ ~C ６ haloalkyl groups), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C１ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group is not a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ alkylamino group (the amino group may be substituted with one or more substituents selected from the substituent group γ), cyano group), 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ) or a cyano group), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with a substituent selected from the substituent group γ) and a cyano group), and the substituent group γ is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C１ ~C ６ haloalkyl groups), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ haloalkylcarbonyl group, or C １ ~C ６ 2. A nicotinamide derivative or a salt thereof, wherein:

[0013] (3) An agricultural and horticultural plant disease control agent, characterized by containing the nicotinamide derivative or its salt according to (2) above as an active ingredient.

[0014] (4) The agricultural and horticultural plant disease control agent according to (1) or (3), wherein the plant disease is caused by a pathogenic fungus.

[0015] (5) The agricultural and horticultural plant disease control agent according to (4), wherein the plant disease is classified into any of the following: Fungi (Basidiomycota, Ascomycota, Mucoromycota, etc.), Stramenopila (Oomycetes, etc.), Rhizaria (Cercozoa, etc.), and Bacteria.

[0016] (6) The agricultural and horticultural plant disease control agent according to (4), wherein the plant disease is classified as Stramenopila (oomycetes, etc.).

[0017] (7) An agricultural or horticultural plant disease control agent comprising the nicotinamide derivative or its salt according to (2) above and an agriculturally acceptable carrier.

[0018] (8) A method for controlling plant diseases by using an effective amount of the nicotinamide derivative or its salt according to (2) above, by spraying, soil application, surface application, seed treatment, immersion, poison bait, or fumigation.

[0019] (9) The method according to (8) above, wherein the useful plant or a part of the useful plant, or the area where the useful plant grows, is sprayed, or seeds of the useful plant are used for seed treatment.

[0020] (10) The method according to (8), wherein the plant disease is caused by a pathogenic fungus.

[0021] (11) The method according to (9), wherein the plant disease is caused by a pathogenic fungus.

[0022] (12) The method according to (10), wherein the plant disease is classified into any of the kingdom Fungi (Basidiomycota, Ascomycota, Mucoromycota, etc.), Stramenopila (Oomycota, etc.), kingdom Rhizaria (Cercozoa, etc.), and bacteria.

[0023] (13) The method according to (11), wherein the plant disease is classified into any of the kingdom Fungi (Basidiomycota, Ascomycota, Mucoromycota, etc.), Stramenopila (Oomycota, etc.), kingdom Rhizaria (Cercozoa, etc.), and bacteria.

[0024] (14) The method according to (10), wherein the plant disease is classified into Stramenopila (Oomycetes, etc.).

[0025] (15) The method according to (11), wherein the plant disease is classified into Stramenopila (Oomycetes, etc.).

[0026] (16) Use of the nicotinamide derivative or its salt according to (2) above as an agricultural and horticultural plant disease control agent for useful plants.

[0027] The nicotinamide derivatives or salts thereof, which are the compounds of the present invention, are useful as active ingredients of agricultural chemicals such as agricultural and horticultural plant disease control agents.

[0028] The agricultural and horticultural plant disease control agent containing the compound of the present invention exhibits excellent control effects against a wide range of plant diseases caused by fungi (Basidiomycota, Ascomycota, Mucoromycota, etc.), Stramenopila (Oomycetes, etc.), Rhizaria (Cercozoa, etc.), bacteria, etc., and can also control fungi that have acquired drug resistance.

[0029] The method for controlling plant diseases of the present invention involves spraying an effective amount of the nicotinamide derivative or a salt thereof of the present invention onto a useful plant or a part of a useful plant, or onto a location where the plant is growing, thereby exhibiting excellent control effects against a wide range of plant diseases and also being able to control fungi that have acquired drug resistance.

[0030] By using the nicotinamide derivative or a salt thereof of the present invention, the nicotinamide derivative or a salt thereof is effective as an agricultural and horticultural plant disease control agent for useful plants, and excellent control effects can be obtained against a wide range of plant diseases, and fungi that have acquired drug resistance can also be controlled.

[0031] The symbols and terms used in this specification will be explained below.

[0032] In the present invention, the term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0033] In the present invention, "C １ ~C ６ " indicates that the following substituent has 1 to 6 carbon atoms in this case.

[0034] In the present invention, "C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, 3-methyl-2-butyl, tert-pentyl, 1,1-dimethylpropyl, isopentyl, neopentyl, sec-pentyl, n-hexyl, 2-hexyl, 3-hexyl, 2-methyl-1-pentyl, 3-methyl-1-pentyl, 4-methyl-1-pentyl, 2-methyl-2-pentyl, 2,3-dimethyl-2-butyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 2,2-dimethyl-1-butyl, 2,3-dimethyl-1-butyl, and 3,3-dimethyl-1-butyl.

[0035] In the present invention, "C １ ~C ６Unless otherwise specified, the term "haloalkyl group" refers to a linear or branched haloalkyl group having 1 to 6 carbon atoms substituted with 1 to 13 identical or different halogen atoms, and examples thereof include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, and the like. fluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 1,1,2,2-tetrachloroethyl, pentachloroethyl, 1-bromoethyl, 2-bromoethyl, 2,2,2-tribromoethyl, 1-iodoethyl, 2-iodoethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1,1-difluoroethyl, Fluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-fluoro-2-propyl, 2-fluoro-2-propyl, 1,1-difluoro-2-propyl, 1,2-difluoro-2-propyl, 1,3-difluoro-2-propyl, 1,2,3-trifluoro-2-propyl, 1,1,3,3-tetrafluoro-2-propyl, 1,1,1,3,3,3-hexafluoro-2-propyl, heptafluoro-2-propyl propyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 1,1-dichloropropyl, 2,2-dichloropropyl, 3,3-dichloropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentachloropropyl, heptachloropropyl, 1-chloro-2-propyl, 2-chloro-2-propyl, 1,1-dichloro-2-propyl, 1,2-dichloro-2-propyl, 1,3-dichloro-2-propyl, 1,2,3-trichloro-2-propyl, 1,1,3,3-tetrachloro-2-propyl, 1,1,1,3,3,3-hexachloro-2-propyl, heptachloro-2-propyl, 1-bromopropyl, 2-bromopropyl, 3-bromopropyl, 1-bromo-2-propyl, 2-bromo-2-propyl, 1-iodopropyl, 2-iodopropyl, 3-iodopropyl, 1-iodo-2-propyl, 2-iodo-2-propyl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4,4-trifluorobutyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,3,4, 4,4-heptafluorobutyl, nonafluorobutyl, 1,1,1-trifluoro-2-butyl, 4,4,4-trifluoro-2-butyl, 3,3,4,4,4-pentafluoro-2-butyl, nonafluoro-2-butyl, 1-fluoro-1,1-dimethylethyl, 1,1-difluoro-2-methyl-2-propyl, 2-trifluoromethyl-2-propyl, 1,1,1,3,3,3-hexafluoro-2-methyl-2-propyl, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propyl, 1,1,1-tri Fluoro-2-methyl-2-butyl, 4,4,4-trifluoro-2-methyl-2-butyl, 3,3-difluoro-2-methyl-2-butyl, 2-methyl-3,3,4,4,4-pentafluoro-2-butyl, 1-chlorobutyl, 2-chlorobutyl, 3-chlorobutyl, 4-chlorobutyl, 4,4-dichlorobutyl, 4,4,4-trichlorobutyl, nonachlorobutyl, 1,1,1-trichloro-2-butyl, 4,4,4-trichloro-2-butyl, nonachloro-2-butyl, 1-bromobutyl, 2-bromobutyl, 3-bromobutyl, 4-bromobutyl mobutyl, 1-iodobutyl, 2-iodobutyl, 3-iodobutyl, 4-iodobutyl, 4-chloro-1,1,2,2,3,3,4,4-octafluorobutyl, 4-bromo-1,1,2,2,3,3,4,4-octafluorobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5-fluoropentyl, 5,5,5-trifluoropentyl, 4,4,5,5,5-pentafluoropentyl, 3,3,4,4,5,5,5-heptafluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, undecafluoropentyl, 1-chloropentyl, 2-chloropentyl, 3-chloropentyl, 4-chloropentyl, 5-chloropentyl, 5,5,5-trichloropentyl, 4,4,5,5,5-pentachloropentyl, 3,3,4,4,5,5,5-heptachloropentyl, 2,2,3,3,4,4,5,5,5-nonachloropentyl, undecachloropentyl, 1-bromopentyl, 2-bromopentyl, 3-bromopentyl, 4-bromopentyl, 5-bromopentyl, 5-iodopentyl, 1-fluorohexyl, 2-fluorohexyl, 3-fluorohexyl, 4-fluorohexyl Examples of groups include 1-chlorohexyl, 5-fluorohexyl, 6-fluorohexyl, 6,6,6-trifluorohexyl, 5,5,6,6,6-pentafluorohexyl, 4,4,5,5,6,6,6-heptafluorohexyl, 3,3,4,4,5,5,6,6,6-nonafluorohexyl, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyl, tridecafluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, 5-chlorohexyl, 6-chlorohexyl, 5-bromohexyl, 6-bromohexyl, 5-iodohexyl, and 6-iodohexyl.

[0036] In the present invention, "C ３ ~C ８ Unless otherwise specified, the term "cycloalkyl group" refers to a cycloalkyl group having 3 to 8 carbon atoms, and the ring may be optionally substituted with an alkyl group within the specified range of carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.

[0037] In the present invention, "C ３ ~C ８Unless otherwise specified, the term "halocycloalkyl group" refers to a cycloalkyl group having 3 to 8 carbon atoms substituted with 1 to 11 identical or different halogen atoms, and the ring may be optionally substituted with an alkyl group or a haloalkyl group within the specified range of carbon atoms. For example, 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl, 1-chlorocyclopropyl, 2-chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2,3,3-tetrachlorocyclopropyl, 1-bromocyclopropyl, 2,2-dibromocyclopropyl, 1-iodocyclopropyl, 1-fluoromethylcyclopropyl, 2,2-diiodocyclopropyl, 1-fluorocyclobutyl, 2-fluorocyclobutyl, 3-fluorocyclobutyl, 3,3-difluorocyclobutyl, heptafluorocyclobutyl, 2-chlorocyclobutyl, 3-chlorocyclobutyl, 3,3-dichlorocyclobutyl, 3,3-dibromocyclobutyl, 3,3-diiodocyclobutyl, 1-fluorocyclopentyl, 2-fluorocyclopentyl, 3-fluorocyclopentyl, 2,2-difluorocyclopentyl, 3, 3-Difluorocyclopentyl, nonafluorocyclopentyl, 2,2-dichlorocyclopentyl, 3,3-dichlorocyclopentyl, 2,2-dibromocyclopentyl, 3,3-dibromocyclopentyl, 2,2-diiodocyclopentyl, 3,3-diiodocyclopentyl, 1-fluorocyclohexyl, 2-fluorocyclohexyl, 3-fluorocyclohexyl, 4-fluorocyclohexyl, 2,2-difluorocyclohexyl, 3,3-difluorocyclohexyl Examples of groups include 1-chlorocyclohexyl, 2-chlorocyclohexyl, 3-chlorocyclohexyl, 4-chlorocyclohexyl, 2,2-dichlorocyclohexyl, 3,3-dichlorocyclohexyl, 4,4-dichlorocyclohexyl, 3,3-dibromocyclohexyl, 4,4-dibromocyclohexyl, 3,3-diiodocyclohexyl, and 4,4-diiodocyclohexyl.

[0038] In the present invention, "C ２ ~C６ Unless otherwise specified, the term "alkenyl group" refers to a straight-chain or branched-chain alkenyl group having 2 to 6 carbon atoms, and examples thereof include vinyl, 1-propenyl, isopropenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1,3-butadienyl, 1-pentenyl, 1-penten-3-yl, 2-pentenyl, and the like. thenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 1-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-2-butenyl, 2-methyl-3-butenyl, 2-methyl-3-buten-2-yl, 3-methyl-1-butenyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, 3-methyl-3-buten-2-yl, 1,3-pentadienyl, 1,4-pentadienyl, 1-hexenyl, 2 -hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 1-methyl-4-pentenyl, 2-methyl-1-penten-3-yl, 2-methyl-2-pentenyl, 2-methyl-4-penten-2-yl, 3-methyl-1-buten-2-yl, 3-methyl-3-pentenyl, 3-methyl-4-pentenyl, 3-methyl-1-penten-3-yl, 3-methyl-4-penten-2-yl, 4 4-methyl-1-penten-3-yl, 4-methyl-3-pentenyl, 4-methyl-3-penten-2-yl, 4-methyl-4-pentenyl, 4-methyl-4-penten-2-yl, 1-hexen-3-yl, 4-hexen-3-yl, 5-hexen-3-yl, 2,3-dimethyl-3-buten-2-yl, 1,5-hexadienyl, 1,5-hexadien-3-yl, or 2,4-hexadienyl groups can be mentioned.

[0039] In the present invention, "C ３ ~C ８ Unless otherwise specified, the term "cycloalkenyl group" refers to a cycloalkenyl group having 3 to 6 carbon atoms, and examples thereof include 1-cyclopropen-1-yl, 1-cyclobuten-1-yl, 1-cyclopenten-1-yl, 1-cyclohexen-1-yl, 1-cyclohepten-1-yl, and 1-cycloocten-1-yl.

[0040] In the present invention, "C ２ ~C ６ Unless otherwise specified, the term "alkynyl group" refers to a straight-chain or branched-chain alkynyl group having 2 to 6 carbon atoms, and examples thereof include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 1-methyl-2-propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-ethyl-2-propynyl, 2-pentynyl, 3-pentynyl, 1-methyl-2-butynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-hexynyl, 1-(n- Examples of such groups include 1-(isopropyl)-2-propynyl, 2-hexynyl, 1-ethyl-2-butynyl, 3-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 4-methyl-1-pentynyl, 3-methyl-1-pentynyl, 5-hexynyl, 1-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl, 1-(isopropyl)-2-propynyl, 1,1-dimethyl-2-butynyl, and 2,2-dimethyl-3-butynyl.

[0041] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl portion of the "alkoxy group" has the above meaning (C １ ~C ６ alkyl)-O- group, and examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, and n-hexyloxy groups.

[0042] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkyloxy group" has the above meaning (C ３ ~C ８cycloalkyl)-O- group, and examples thereof include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, and cyclooctyloxy groups.

[0043] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkyloxy group" has the above meaning (C １ ~C ６haloalkyl)-O- group, and examples thereof include difluoromethoxy, dichloromethoxy, trifluoromethoxy, trichloromethoxy, tribromomethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 1-chloroethoxy, 2-chloroethoxy, 1-bromoethoxy, 2-bromoethoxy, 2,2-difluoroethoxy, 1,2-dichloroethoxy, 2,2-dichloroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 1,1,2,2-tetrafluoroethoxy, pentafluoroethoxy, oxy, 2-bromo-2-chloroethoxy, 2-chloro-1,1,2,2-tetrafluoroethoxy, 1-chloro-1,2,2,2-tetrafluoroethoxy, 1-chloropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2-bromo-1-methylethoxy, 3-iodopropoxy, 2,3-dichloropropoxy, 2,3-dibromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trifluoro-2-propoxy, 3,3,3-trichloropropoxy, 3-bromo-3,3-difluoropropoxy fluoropropoxy, 2,2-difluoropropoxy, 3,3-dichloro-3-fluoropropoxy, 2,2,3,3-tetrafluoropropoxy, 1-bromo-3,3,3-trifluoropropoxy, 2,2,3,3,3-pentafluoropropoxy, 2,2,2-trifluoro-1-trifluoromethylethoxy, heptafluoropropoxy, heptafluoro-2-propoxy, 1,2,2,2-tetrafluoro-1-trifluoromethylethoxy, 1,1,2,3,3,3-hexafluoropropoxy, 2-chlorobutoxy, 3-chlorobutoxy, 4 -chlorobutoxy, 2-chloro-1,1-dimethylethoxy, 4-bromobutoxy, 3-bromo-2-methylpropoxy, 2-bromo-1,1-dimethylethoxy, 2,2-dichloro-1,1-dimethylethoxy, 2-chloro-1-chloromethyl-2-methylethoxy, 4,4,4-trifluorobutoxy, 3,3,3-trifluoro-1-methylpropoxy, 3,3,3-trifluoro-2-methylpropoxy, 2,3,4-trichlorobutoxy, 2,2,2-trichloro-1,1-dimethylethoxy, 4-chloro-4,4-difluorobutoxy, 4,4-dichloro-4-fluorobutoxy, 4-bromo-4,4-difluorobutoxy, 2,4-dibromo-4,4-difluorobutoxy, 3,4-dichloro-3,4,4-trifluorobutoxy, 3,3-dichloro-4,4,4-trifluorobutoxy, 4-bromo-3,3,4,4-tetrafluorobutoxy, 4-bromo-3-chloro-3,4,4-trifluorobutoxy, 2,2,3,3,4,4-hexafluorobutoxy, 2,2,3,4,4,4-hexafluorobutoxy, 2 , 2,2-trifluoro-1-methyl-1-trifluoromethylethoxy, 3,3,3-trifluoro-2-trifluoromethylpropoxy, 2,2,3,3,4,4,4-heptafluorobutoxy, 3,3,4,4,4-pentafluoro-2-butoxy, 2,3,3,3-tetrafluoro-2-trifluoromethylpropoxy, 1,1,2,2,3,3,4,4-octafluorobutoxy, nonafluorobutoxy, perfluoro-tert-butoxy, 4-chloro-1,1,2,2, 3,3,4,4-octafluorobutoxy, 5,5,5-trifluoropentoxy, 4,4,5,5,5-pentafluoropentoxy, 3,3,4,4,5,5,5-heptafluoropentoxy, 3,3,4,4,5,5,5-heptafluoro-2-pentoxy, 2,2,3,3,4,4,5,5,5-nonafluoropentoxy, 2,2,3,3,4,4,5,5-octafluoropentoxy, perfluoropentoxy, 4,4,5,5,5-pentafluoro-2-butoxy, 2,2 4,4,4-trifluoro-3,3-bis(trifluoromethyl)propoxy, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexyloxy, 3,3,4,4,5,5,6,6,6-nonafluorohexyloxy, 4,4,5,5,6,6,6-heptafluorohexyloxy, 2,2,3,3,4,4,5,5,6,6-decafluorohexyloxy, 4,4,4-trifluoro-3,3-bis(trifluoromethyl)butyloxy, and perfluorohexyloxy groups can be mentioned.

[0044] In the present invention, "C ２ ~C ６ Unless otherwise specified, the alkenyl moiety of the "alkenyloxy group" has the above meaning (C ２ ~C６ alkenyl)-O- group, and examples thereof include vinyloxy, 1-propenyloxy, isopropenyloxy, 2-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, and 5-hexenyloxy groups.

[0045] In the present invention, "C ２ ~C ６ Unless otherwise specified, the alkynyl moiety of the "alkynyloxy group" has the above meaning (C ２ ~C ６ alkynyl)-O- group, and examples thereof include ethynyloxy, 1-propynyloxy, 2-propynyloxy, 1-methyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 1-butynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-butynyloxy, 1-pentynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, and 4,4-dimethyl-2-pentynyloxy groups.

[0046] In the present invention, "tori (C １ ~C ６ Unless otherwise specified, the alkyl portion of the "silyloxy group" is defined as above (C １ ~C ６ alkyl) ３ It represents an —Si—O— group, and the three alkyl groups may be the same or different from one another. Examples include trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, dimethylisopropylsilyloxy, and tert-butyldimethylsilyloxy groups.

[0047] In the present invention, "C ６ ~C １２Unless otherwise specified, the term "aryl group" refers to an aryl group having 6 to 12 carbon atoms, and examples thereof include phenyl, 2-biphenyl, 4-biphenyl, naphthalen-1-yl, and naphthalen-2-yl.

[0048] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroaryl group" refers to a 5- to 12-membered monocyclic or fused bicyclic aromatic heterocycle containing, in addition to carbon atoms, one or more heteroatoms selected from a nitrogen atom, an oxygen atom, and a sulfur atom. Examples of the monocyclic aromatic heterocycle include pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, 1,2,3-triazin-4-yl, 1,2,3-triazin-5-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl, 1,3,5-triazinyl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyran-2-yl, pyran-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl yl, isothiazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, 1,4,5-triazol-1-yl, 1,4,5-triazol-4-yl, 1,4,5-triazol-5-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1 ,3,4-thiadiazol-2-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,5-oxadiazol-3-yl, or 1,3,5-triazinin-2-yl, and the fused bicyclic heterocycles include those in which one of the monocyclic groups is connected to a phenyl ring, or one of the heteroaromatic monocyclic groups is connected to a C, ８ ~C １０Fused bicyclic moieties formed by condensing to form a bicyclic group, e.g., indolyl-1-yl, indolyl-2-yl, indolyl-3-yl, indolyl-4-yl, indolyl-5-yl, indolyl-6-yl, indolyl-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, benzimidazol-6-yl, benzimidazol-7-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazo Indazol-5-yl, indazol-6-yl, indazol-7-yl, benzotriazol-1-yl, benzotriazol-4-yl, benzotriazol-5-yl, benzotriazol-6-yl, benzotriazol-7-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl, quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl yl, quinolin-8-yl, benzothiazol-2-yl, benzothiazol-4-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzothiazol-7-yl, benzofuran-2-yl, benzofuran-3-yl, benzofuran-4-yl, benzofuran-5-yl, benzofuran-6-yl, benzofuran-7-yl, benzothiophen-2-yl, benzothiophen-3-yl, benzothiophen-4-yl, benzothiophen-5-yl, benzothiophen-6-yl, benzothiophen-7-yl, benzisoxazo benzisoxazol-3-yl, benzisoxazol-4-yl, benzisoxazol-5-yl, benzisoxazol-6-yl, benzisoxazol-7-yl, pyrazolopyridin-1-yl, pyrazolopyridin-3-yl, pyrazolopyridin-4-yl, pyrazolopyridin-5-yl, pyrazolopyridin-6-yl, pyrazolopyrimidin-1-yl, pyrazolopyrimidin-2-yl, pyrazolopyrimidin-3-yl, pyrazolopyrimidin-5-yl, pyrazolopyrimidin-6-yl, pyrazolopyrimidin-7-yl, pyrrolopyridin-1-yl,Pyrrolopyridin-2-yl, pyrrolopyridin-3-yl, pyrrolopyridin-4-yl, pyrrolopyridin-5-yl, pyrrolopyridin-6-yl, triazolopyridin-3-yl, triazolopyridin-4-yl, triazolopyridin-5-yl, triazolopyridin-6-yl, triazolopyridin-7-yl, triazolopyrimidin-2-yl, triazolopyrimidin-3-yl, triazolopyrimidin-6-yl, triazolopyrimidin-7-yl, quinazoline-2 quinazolin-4-yl, quinazolin-5-yl, quinazolin-6-yl, quinazolin-7-yl, quinazolin-8-yl, quinoxalin-2-yl, quinoxalin-3-yl, quinoxalin-5-yl, quinoxalin-6-yl, quinoxalin-7-yl, quinoxalin-8-yl, cinnolin-3-yl, cinnolin-4-yl, cinnolin-5-yl, cinnolin-6-yl, cinnolin-7-yl, or cinnolin-8-yl groups, etc., can be mentioned.

[0049] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclyl group" refers to a 3- to 6-membered non-aromatic heterocycle containing, in addition to carbon atoms, one or more atoms selected from oxygen atoms, nitrogen atoms, sulfur atoms, and boron atoms, and examples thereof include aziridin-1-yl, aziridin-2-yl, oxiran-2-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, and the like. yl, pyrrolidin-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperazin-1-yl, piperazin-2-yl, 4,5-dihydroisoxazol-3-yl, 1,3,2-dioxaborolan-2-yl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 5-oxo-4,5-dihydro-1,2,4-oxadiazol-2-yl, 5-oxo-4,5-dihydro-1,2,4-thiadiazol-2-yl, 5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl, 5-oxo-4,5-dihydro-1,3,4-thiadiazol-2-yl, or morpholin-4-yl groups can be mentioned.

[0050] In the present invention, "C ３ ~C ８ Cycloalkyl C ２ ~C ６ Unless otherwise specified, the cycloalkyl and alkynyl moieties of the "alkynyl group" have the same meanings as above (C ３ ~C ８ cycloalkyl)-(C ２ ~C ６ alkynyl)-group, and examples thereof include cyclopropylethynyl, cyclobutylethynyl, cyclopentylethynyl, cyclohexylethynyl, cyclooctylethynyl, and 3-(cyclopropyl)-2-propynyl groups.

[0051] In the present invention, "hydroxy C １ ~C６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (hydroxy)-(C １ ~C ６ alkyl)-groups, and examples thereof include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxypropan-2-yl, 3-hydroxy-2-methylpropan-2-yl, 4-hydroxy-2-methylbutan-2-yl, and 5-hydroxy-2-methylpentan-2-yl groups.

[0052] In the present invention, "mercapto C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (mercapto)-(C １ ~C ６ alkyl)-groups, and examples thereof include mercaptomethyl, 1-mercaptoethyl, 2-mercaptoethyl, 2-mercaptopropan-2-yl, 3-mercapto-2-methylpropan-2-yl, 4-mercapto-2-methylbutan-2-yl, and 5-mercapto-2-methylpentan-2-yl groups.

[0053] In the present invention, "cyano C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (cyano)-(C １ ~C ６ alkyl)-group, and examples thereof include cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyano-2-propyl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl, and 6-cyanohexyl groups.

[0054] In the present invention, "formyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (formyl)-(C １ ~C ６alkyl)-group, and examples thereof include formylmethyl, 1-formylethyl, 2-formylethyl, 1-formylpropyl, 3-formylpropyl, 2-formyl-2-propyl, 1-formylbutyl, 4-formylbutyl, 5-formylpentyl, and 6-formylhexyl groups.

[0055] In the present invention, "carboxyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (carboxyl)-(C １ ~C ６ alkyl)-group, and examples thereof include carboxylmethyl, 1-carboxylethyl, 2-carboxylethyl, 1-carboxylpropyl, 3-carboxylpropyl, 2-carboxyl-2-propyl, 1-carboxylbutyl, 4-carboxylbutyl, 5-carboxylpentyl, and 6-carboxyhexyl groups.

[0056] In the present invention, "amino C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (amino)-(C １ ~C ６ alkyl)-group, and examples thereof include aminomethyl, 1-aminoethyl, 2-aminoethyl, 1-aminopropyl, 3-aminopropyl, 2-amino-2-propyl, 1-aminobutyl, 4-aminobutyl, 5-aminopentyl, and 6-aminohexyl groups.

[0057] In the present invention, "cyanothio C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (cyanothio)-(C １ ~C ６alkyl)-group, and examples thereof include cyanothiomethyl, 1-(cyanothio)ethyl, 2-(cyanothio)ethyl, 1-(cyanothio)propyl, 3-(cyanothio)propyl, 2-(cyanothio)-2-propyl, 1-(cyanothio)butyl, 4-(cyanothio)butyl, 5-(cyanothio)pentyl, and 6-(cyanothio)hexyl groups.

[0058] In the present invention, "aminocarbonyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning. ２ N-C(O)-(C １ ~C ６ alkyl)-group, and examples thereof include carbamoylmethyl, 1-carbamoylethyl, and 2-carbamoylethyl groups.

[0059] In the present invention, "C １ ~C ６ Alkylaminocarbonyl C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-NH-C(O)-(C １ ~C ６ and N-(tert-butyl)carbamoylmethyl, N-methylcarbamoylmethyl, N-ethylcarbamoylmethyl, N-(tert-butyl)carbamoylmethyl, and the like.

[0060] In the present invention, "C １ ~C ６ Alkylaminosulfonylamino C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-NH-S(O) ２ -NH-(C １ ~C ６It represents an [(N-methylsulfamoyl)amino]methyl, [(N-ethylsulfamoyl)amino]methyl, [(N-isopropylsulfamoyl)amino]methyl, 1-[(N-methylsulfamoyl)amino]ethyl, or 2-[(N-methylsulfamoyl)amino]ethyl group, for example.

[0061] In the present invention, "hydroxyaminocarbonyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning (hydroxy)-HN-C(O)-(C １ ~C ６ and 2-(hydroxyamino)-2-oxoethyl, 3-(hydroxyamino)-3-oxopropyl, and the like.

[0062] In the present invention, "aminothiocarbonyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning. ２ N-C(S)-(C １ ~C ６ alkyl)-group, and examples thereof include 2-amino-2-thiooxoethyl, 3-amino-3-thiooxopropyl, and 1-amino-1-thiopropan-2-yl groups.

[0063] In the present invention, "C １ ~C ６ Alkylaminothiocarbonyl C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-NH-C(S)-(C １ ~C ６ alkyl)-group, and examples thereof include 2-(methylamino)-2-thiooxoethyl, 2-(ethylamino)-2-thiooxoethyl, and 1-(methylamino)-1-thiopropan-2-yl groups.

[0064] In the present invention, "tori (C １~C ６ Alkyl)silyl C ２ ~C ６ Unless otherwise specified, the alkyl and alkynyl groups have the same meanings as above (C １ ~C ６ alkyl) ３ -Si-(C ２ ~C ６ alkynyl)-group, and examples thereof include trimethylsilylethynyl, triethylsilylethynyl, triethylsilylethynyl, tert-butyldimethylsilylethynyl, and 3-(trimethylsilyl)-2-propynyl groups.

[0065] In the present invention, "C １ ~C ６ Alkoxy C １ ~C ６ Unless otherwise specified, the alkoxy and alkyl moieties of the "alkyl group" have the same meanings as above (C １ ~C ６ alkoxy)-(C １ ~C ６ alkyl)-group, and examples thereof include methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-methoxy-1-methylethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl, 1-isopropoxyethyl, 1-methoxypropyl, 2-methoxypropyl, 1-ethoxypropyl, 1-methoxybutyl, 1-ethoxybutyl, 3-methoxypropan-2-yl, 3-ethoxypropan-2-yl, 3-methoxy-2-methylpropan-2-yl, 3-ethoxy-2-methylpropan-2-yl, 4-methoxybutan-2-yl, 4-ethoxybutan-2-yl, 4-methoxy-2-methylbutan-2-yl, and 4-ethoxy-2-methylbutan-2-yl groups.

[0066] In the present invention, "C ３ ~C ８ Cycloalkyloxy C １ ~C ６Unless otherwise specified, the cycloalkyl and alkyl moieties of the "alkyl group" have the same meanings as above (C ３ ~C ８ cycloalkyl)-O-(C １ ~C ６ alkyl)-group, and examples thereof include cyclopropoxymethyl, cyclobutoxymethyl, cyclohexyloxymethyl, 1-cyclopropoxyethyl, and 2-cyclopropoxyethyl groups.

[0067] In the present invention, "C １ ~C ６ Haloalkyloxy C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the haloalkyloxy moiety and alkyl moiety have the same meaning as defined above (C １ ~C ６ haloalkyloxy)-(C １ ~C ６ alkyl)-group, and examples thereof include 2-(difluoromethoxy)ethyl, 2-(trifluoromethoxy)ethyl, 2-(2,2-difluoroethoxy)ethyl, 2-(2,2,2-trifluoroethoxy)ethyl, 2-(3,3-difluoropropioxy)ethyl, 2-(3,3,3-trifluoropropioxy)ethyl, 3-(difluoromethoxy)propyl, 3-(trifluoromethoxy)propyl, 3-(2,2-difluoroethoxy)propyl, 3-(2,2,2-trifluoroethoxy)propyl, 3-(3,3-difluoropropioxy)propyl, 3-(3,3,3-trifluoropropioxy)propyl, 4-(trifluoromethoxy)butyl, and 5-(trifluoromethoxy)pentyl groups.

[0068] In the present invention, "C １ ~C ６ Alkoxy C １ ~C ６ Unless otherwise specified, the alkoxy group has the above meaning in the alkoxy moiety (C １ ~C ６ alkoxy)-(C １ ~C ６alkoxy)-groups, and examples thereof include 2-methoxyethoxy, 3-methoxypropoxy, 2-ethoxyisopropoxy, 2-isopropoxybutoxy, 5-ethoxypentyloxy, 6-ethoxyhexyloxy, 2-(tert-butoxy)ethoxy, 2-methoxyisopentyloxy, and 2-isopropoxyisobutoxy groups.

[0069] In the present invention, "C ３ ~C ８ Cycloalkyl C １ ~C ６ Unless otherwise specified, the cycloalkyl and alkoxy moieties of the "alkoxy group" have the same meanings as above (C ３ ~C ８ cycloalkyl)-(C １ ~C ６ alkoxy)-group, and examples thereof include cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, 2-cyclopropylethoxy, 2-cyclobutylethoxy, and 2-cyclopentylethoxy groups.

[0070] In the present invention, "C ６ ~C １２ Aryl C １ ~C ６ Unless otherwise specified, the aryl and alkoxy groups have the same meanings as above (C ６ ~C １２ aryl)-(C １ ~C ６ alkoxy)-group, and examples thereof include benzyloxy, 1-phenylethyloxy, 2-phenylethyloxy, 2-phenylpropyloxy, 2-phenylbutyloxy, 1-phenylpentyloxy, naphthalen-1-ylmethoxy, and naphthalen-2-ylmethoxy groups.

[0071] In the present invention, "5- to 12-membered heteroaryl C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a (5- to 12-membered heteroaryl)-(C １ ~C ６alkoxy)-groups, and examples thereof include pyridylmethoxy, pyrimidinylmethoxy, pyrazinylmethoxy, pyridazinylmethoxy, triazinylmethoxy, thienylmethoxy, furanylmethoxy, pyrrolylmethoxy, pyrazolylmethoxy, thiazolylmethoxy, isothiazolylmethoxy, oxazolylmethoxy, isoxazolylmethoxy, imidazolylmethoxy, triazolylmethoxy, thiadiazolylmethoxy, oxadiazolylmethoxy, tetrazolylmethoxy, indolylmethoxy, benzimidazolylmethoxy, indazolylmethoxy, benzotriazolylmethoxy, isoquinolinylmethoxy, quinolinylmethoxy, benzothiazolylmethoxy, benzofuranylmethoxy, benzothienylmethoxy, benzisoxazolylmethoxy, pyrazolopyridylmethoxy, pyrazolopyrimidinylmethoxy, pyrrolopyridylmethoxy, triazolopyridylmethoxy, triazolopyrimidinylmethoxy, quinazolinylmethoxy, quinoxalinylmethoxy, cinnolinylmethoxy, and pyridylethoxy groups.

[0072] In the present invention, "3- to 6-membered heterocyclyl C １ ~C ６ Unless otherwise specified, the term "alkoxy group" refers to a (3- to 6-membered heterocyclyl)-(C １ ~C ６ alkoxy)-group, and examples thereof include aziridinylmethoxy, oxiranylmethoxy, oxetanylmethoxy, thietanylmethoxy, tetrahydrofuranylmethoxy, tetrahydropyranylmethoxy, azetidinylmethoxy, pyrrolidinylmethoxy, piperidinylmethoxy, piperazinylmethoxy, dihydroisoxazolylmethoxy, dioxaborolanylmethoxy, dioxolanylmethoxy, dioxanylmethoxy, morpholinylmethoxy, and aziridinylethoxy groups.

[0073] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylcarbonyl group" has the above meaning (C １ ~C ６alkyl)-C(O)- group, and examples thereof include acetyl, propionyl, 2-methylpropionyl, 2,2-dimethylpropionyl, butanoyl, 2-methylbutanoyl, 3-methylbutanoyl, 2-ethylbutanoyl, 2,2-dimethylbutanoyl, 2,3-dimethylbutanoyl, 3,3-dimethylbutanoyl, pentanoyl, 2-methylpentanoyl, 3-methylpentanoyl, 4-methylpentanoyl, and hexanoyl groups.

[0074] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylcarbonyl group" has the above meaning (C ３ ~C ８ cycloalkyl)-C(O)- group, and examples thereof include cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl, cycloheptanecarbonyl, and cyclooctanecarbonyl groups.

[0075] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylcarbonyl group" has the same meaning as above (C １ ~C ６ haloalkyl)-C(O)- group, and examples thereof include fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, trichloroacetyl, tribromoacetyl, 3,3,3-trifluoropropionyl, 3,3-difluoropropionyl, and 4,4,4-trifluorobutyryl groups.

[0076] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkoxy moiety of the "alkoxycarbonyl group" has the above meaning (C １ ~C ６alkoxy)-C(O)- group, and examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1-ethylpropoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, and 2,2-dimethylpropoxycarbonyl groups.

[0077] In the present invention, "cyano C １ ~C ６ Unless otherwise specified, the term "alkylcarbonyl group" refers to a group in which the alkyl moiety has the above meaning (cyano)-(C １ ~C ６ alkyl)-C(O)- group, and examples thereof include 2-cyanoacetyl, 2-cyanopropanoyl, and 3-cyanopropanoyl groups.

[0078] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylcarbonyloxy group" has the above meaning (C １ ~C ６ alkyl)-C(O)-O- group, and examples thereof include methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, isopropylcarbonyloxy, n-butylcarbonyloxy, isobutylcarbonyloxy, sec-butylcarbonyloxy, and tert-butylcarbonyloxy groups.

[0079] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylcarbonyloxy group" has the above meaning (C ３ ~C ８cycloalkyl)-C(O)-O- group, and examples thereof include cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, cycloheptylcarbonyloxy, and cyclooctylcarbonyloxy groups.

[0080] In the present invention, "C １ ~C ６ Alkylcarbonylamino C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-C(O)-NH-(C １ ~C ６ alkyl)-group, and examples thereof include 1-acetylamino-1-methylethyl, 1-propionylamino-1-methylethyl, 1-butyrylamino-1-methylethyl, 1-isobutyrylamino-1-methylethyl, 3-acetylamino-2-methylpropan-2-yl, 3-propionylamino-2-methylpropan-2-yl, 3-butyrylamino-2-methylpropan-2-yl, and 3-isobutyrylamino-2-methylpropan-2-yl.

[0081] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylthio group" has the above meaning (C １ ~C ６ alkyl)-S- group, and examples thereof include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and tert-butylthio groups.

[0082] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylsulfinyl group" has the above meaning (C １ ~C ６alkyl)-S(O)- group, and examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, and tert-butylsulfinyl groups.

[0083] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylsulfonyl group" has the above meaning (C １ ~C ６ alkyl)-S(O) ２ - group, and examples thereof include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, and tert-butylsulfonyl groups.

[0084] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylthio group" has the above meaning (C ３ ~C ８ cycloalkyl)-S- group, and examples thereof include cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cycloheptylthio, and cyclooctylthio groups.

[0085] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylsulfinyl group" has the above meaning (C ３ ~C ８ cycloalkyl)-S(O)- group, and examples thereof include cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, cycloheptylsulfinyl, and cyclooctylsulfinyl groups.

[0086] In the present invention, "C ３ ~C ８Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylsulfonyl group" has the above meaning (C ３ ~C ８ cycloalkyl)-S(O) ２ - group, and examples thereof include cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cycloheptylsulfonyl, and cyclooctylsulfonyl groups.

[0087] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylthio group" has the same meaning as defined above (C １ ~C ６ haloalkyl)-S- group, and examples thereof include fluoromethylthio, difluoromethylthio, trifluoromethylthio, trichloromethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, 2,2,2-trichloroethylthio, 3,3,3-trifluoropropylthio, heptafluoropropylthio, 1,1,1,3,3,3-hexafluoro-2-propylthio, heptafluoro-2-propylthio, and 4,4,4-trifluorobutylthio groups.

[0088] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylsulfinyl group" has the same meaning as above (C １ ~C ６ haloalkyl)-S(O)- group, and examples thereof include fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, pentafluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl, 3,3,3-trifluoropropylsulfinyl, heptafluoropropylsulfinyl, 1,1,1,3,3,3-hexafluoro-2-propylsulfinyl, heptafluoro-2-propylsulfinyl, and 4,4,4-trifluorobutylsulfinyl groups.

[0089] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylsulfonyl group" has the same meaning as above (C １ ~C ６ haloalkyl)-S(O) ２ - group, and examples thereof include fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, pentafluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, 3,3,3-trifluoropropylsulfonyl, heptafluoropropylsulfonyl, 1,1,1,3,3,3-hexafluoro-2-propylsulfonyl, heptafluoro-2-propylsulfonyl, and 4,4,4-trifluorobutylsulfonyl groups.

[0090] In the present invention, "C ３ ~C ８ Cycloalkyl C １ ~C ６ Unless otherwise specified, the cycloalkyl and alkylthio moieties of the "alkylthio group" have the same meanings as above (C ３ ~C ８ cycloalkyl)-(C １ ~C ６ alkylthio)-group, and examples thereof include cyclopropylmethylthio, 2-cyclopropylethylthio, 3-cyclopropylpropylthio, 4-cyclopropylbutylthio, 5-cyclopropylpentylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, and cyclooctylmethylthio groups.

[0091] In the present invention, "C ３ ~C ８ Cycloalkyl C １ ~C ６ Unless otherwise specified, the cycloalkyl and alkylsulfinyl moieties of the "alkylsulfinyl group" have the same meanings as above (C ３ ~C ８ cycloalkyl)-(C １ ~C ６alkylsulfinyl)-group, and examples thereof include (cyclopropylmethyl)sulfinyl, (cyclobutylmethyl)sulfinyl, (cyclopentylmethyl)sulfinyl, (cyclooctylmethyl)sulfinyl, (2-cyclopropylethyl)sulfinyl, (2-cyclobutylethyl)sulfinyl, (2-cyclopentylethyl)sulfinyl, and (2-cyclooctylethyl)sulfinyl groups.

[0092] In the present invention, "C ３ ~C ８ Cycloalkyl C １ ~C ６ Unless otherwise specified, the cycloalkyl moiety and alkylsulfonyl moiety of the "alkylsulfonyl group" have the same meaning as above (C ３ ~C ８ cycloalkyl)-(C １ ~C ６ alkylsulfonyl-group, and examples thereof include (cyclopropylmethyl)sulfonyl, (cyclobutylmethyl)sulfonyl, (cyclopentylmethyl)sulfonyl, (cyclooctylmethyl)sulfonyl, (2-cyclopropylethyl)sulfonyl, (2-cyclobutylethyl)sulfonyl, (2-cyclopentylethyl)sulfonyl, and (2-cyclooctylethyl)sulfonyl groups.

[0093] In the present invention, "C １ ~C ６ Alkoxy C １ ~C ６ Unless otherwise specified, the alkoxy moiety and alkylthio moiety of the "alkylthio group" have the same meaning as above (C １ ~C ６ alkoxy)-(C １ ~C ６ alkylthio)-group, and examples thereof include (2-methoxyethyl)thio, (3-methoxypropyl)thio, (2-isopropoxyethyl)thio, (2-isopropoxybutyl)thio, (5-ethoxypentyl)thio, (6-ethoxyhexyl)thio, and (1-methoxypropan-2-yl)thio groups.

[0094] In the present invention, "C１ ~C ６ Alkoxy C １ ~C ６ Unless otherwise specified, the alkoxy moiety and alkylsulfinyl moiety of the "alkylsulfinyl group" have the same meaning as above (C １ ~C ６ alkoxy)-(C １ ~C ６ alkylsulfinyl-group, and examples thereof include (2-methoxyethyl)sulfinyl, (3-methoxypropyl)sulfinyl, (2-isopropoxyethyl)sulfinyl, (2-isopropoxybutyl)sulfinyl, (5-ethoxypentyl)sulfinyl, (6-ethoxyhexyl)sulfinyl, and (1-methoxypropan-2-yl)sulfinyl groups.

[0095] In the present invention, "C １ ~C ６ Alkoxy C １ ~C ６ Unless otherwise specified, the alkoxy moiety and alkylsulfonyl moiety of the "alkylsulfonyl group" have the same meaning as above (C １ ~C ６ alkoxy)-(C １ ~C ６ alkylsulfonyl-group, and examples thereof include (2-methoxyethyl)sulfonyl, (3-methoxypropyl)sulfonyl, (2-isopropoxyethyl)sulfonyl, (2-isopropoxybutyl)sulfonyl, (5-ethoxypentyl)sulfonyl, (6-ethoxyhexyl)sulfonyl, and (1-methoxypropan-2-yl)sulfonyl groups.

[0096] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylaminosulfonyl group" has the above meaning (C １ ~C ６ alkyl)-NH-S(O) ２ - group, and examples thereof include methylaminosulfonyl, ethylaminosulfonyl, and isobutylaminosulfonyl groups.

[0097] In the present invention, "C １ ~C ６ Alkylthio C １ ~C ６ Unless otherwise specified, the alkyl group has the above-mentioned meanings for the alkylthio and alkyl moieties (C １ ~C ６ alkylthio)-(C １ ~C ６ alkyl)-group, and examples thereof include 1-methylthio-1-methylethyl, 1-ethylthio-1-methylethyl, 1-n-propylthio-1-methylethyl, 1-isopropylthio-1-methylethyl, 3-methylthio-2-methylpropan-2-yl, 3-ethylthio-2-methylpropan-2-yl, 3-n-propylthio-2-methylpropan-2-yl, and 3-isopropylthio-2-methylpropan-2-yl groups.

[0098] In the present invention, "C １ ~C ６ Alkylsulfinyl C １ ~C ６ Unless otherwise specified, the alkyl group "has the same meaning as above in the alkylsulfinyl moiety and alkyl moiety (C １ ~C ６ alkylsulfinyl)-(C １ ~C ６ alkyl)-group, and examples thereof include 1-methylsulfinyl-1-methylethyl, 1-ethylsulfinyl-1-methylethyl, 1-n-propylsulfinyl-1-methylethyl, 1-isopropylsulfinyl-1-methylethyl, 3-methylsulfinyl-2-methylpropan-2-yl, 3-ethylsulfinyl-2-methylpropan-2-yl, 3-n-propylsulfinyl-2-methylpropan-2-yl, and 3-isopropylsulfinyl-2-methylpropan-2-yl groups.

[0099] In the present invention, "C １ ~C ６ Alkylsulfonyl C １ ~C ６ Unless otherwise specified, the alkyl group "has the same meaning as above in the alkylsulfonyl moiety and alkyl moiety (C１ ~C ６ alkylsulfonyl)-(C １ ~C ６ alkyl)-group, and examples thereof include 1-methylsulfonyl-1-methylethyl, 1-ethylsulfonyl-1-methylethyl, 1-n-propylsulfonyl-1-methylethyl, 1-isopropylsulfonyl-1-methylethyl, 3-methylsulfonyl-2-methylpropan-2-yl, 3-ethylsulfonyl-2-methylpropan-2-yl, 3-n-propylsulfonyl-2-methylpropan-2-yl, and 3-isopropylsulfonyl-2-methylpropan-2-yl groups.

[0100] In the present invention, "C １ ~C ６ Haloalkylthio C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the haloalkylthio moiety and alkyl moiety have the same meaning as defined above (C １ ~C ６ haloalkylthio)-(C １ ~C ６ alkyl)- group, and examples thereof include (difluoromethylthio)methyl, (trifluoromethylthio)methyl, (2,2-difluoroethylthio)methyl, (2,2,2-trifluoroethylthio)methyl, 2-(difluoromethylthio)ethyl, 2-(trifluoromethylthio)ethyl, 2-(2,2-difluoroethylthio)ethyl, 2-(2,2,2-trifluoroethylthio)ethyl, 3-(difluoromethylthio)propyl, 3-(trifluoromethylthio)propyl, 3-(2,2-difluoroethylthio)propyl, and 3-(2,2,2-trifluoroethylthio)propyl groups.

[0101] In the present invention, "C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the haloalkylsulfinyl moiety and alkyl moiety have the same meaning as defined above (C １ ~C ６ haloalkylsulfinyl)-(C１ ~C ６ alkyl)- group, and examples thereof include (difluoromethylsulfinyl)methyl, (trifluoromethylsulfinyl)methyl, (2,2-difluoroethylsulfinyl)methyl, (2,2,2-trifluoroethylsulfinyl)methyl, 2-(difluoromethylsulfinyl)ethyl, 2-(trifluoromethylsulfinyl)ethyl, 2-(2,2-difluoroethylsulfinyl)ethyl, 2-(2,2,2-trifluoroethylsulfinyl)ethyl, 3-(difluoromethylsulfinyl)propyl, 3-(trifluoromethylsulfinyl)propyl, 3-(2,2-difluoroethylsulfinyl)propyl, and 3-(2,2,2-trifluoroethylsulfinyl)propyl groups.

[0102] In the present invention, "C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the haloalkylsulfonyl moiety and alkyl moiety have the same meaning as defined above (C １ ~C ６ haloalkylsulfonyl)-(C １ ~C ６ alkyl)- group, and examples thereof include (difluoromethylsulfonyl)methyl, (trifluoromethylsulfonyl)methyl, (2,2-difluoroethylsulfonyl)methyl, (2,2,2-trifluoroethylsulfonyl)methyl, 2-(difluoromethylsulfonyl)ethyl, 2-(trifluoromethylsulfonyl)ethyl, 2-(2,2-difluoroethylsulfonyl)ethyl, 2-(2,2,2-trifluoroethylsulfonyl)ethyl, 3-(difluoromethylsulfonyl)propyl, 3-(trifluoromethylsulfonyl)propyl, 3-(2,2-difluoroethylsulfonyl)propyl, and 3-(2,2,2-trifluoroethylsulfonyl)propyl groups.

[0103] In the present invention, "C ３ ~C ８ Cycloalkylthio C １ ~C ６Unless otherwise specified, the cycloalkylthio moiety and alkyl moiety of the "alkyl group" have the same meaning as above (C ３ ~C ８ cycloalkylthio)-(C １ ~C ６ alkyl)-group, and examples thereof include (cyclopropylthio)methyl, (cyclobutylthio)methyl, (cyclopentylthio)methyl, (cyclohexylthio)methyl, (cyclooctylthio)methyl, 1-(cyclopropylthio)ethyl, and 2-(cyclopropylthio)ethyl groups.

[0104] In the present invention, "C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ Unless otherwise specified, the cycloalkylsulfinyl moiety and alkyl moiety have the same meaning as above (C ３ ~C ８ cycloalkylsulfinyl)-(C １ ~C ６ alkyl)-group, and examples thereof include (cyclopropylsulfinyl)methyl, (cyclobutylsulfinyl)methyl, (cyclopentylsulfinyl)methyl, (cyclohexylsulfinyl)methyl, (cyclooctylsulfinyl)methyl, 1-(cyclopropylsulfinyl)ethyl, and 2-(cyclopropylsulfinyl)ethyl groups.

[0105] In the present invention, "C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ Unless otherwise specified, the cycloalkylsulfonyl moiety and alkyl moiety have the same meaning as above (C ３ ~C ８ Cycloalkylsulfonyl)-(C １ ~C ６alkyl)-group, and examples thereof include (cyclopropylsulfonyl)methyl, (cyclobutylsulfonyl)methyl, (cyclopentylsulfonyl)methyl, (cyclohexylsulfonyl)methyl, (cyclooctylsulfonyl)methyl, 1-(cyclopropylsulfonyl)ethyl, and 2-(cyclopropylsulfonyl)ethyl groups.

[0106] In the present invention, "C １ ~C ６ Alkoxycarbonyl C １ ~C ６ Unless otherwise specified, the alkoxy and alkyl moieties of the "alkyl group" have the same meanings as above (C １ ~C ６ alkoxy)-C(O)-(C １ ~C ６ alkyl)-group, and examples thereof include methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propoxycarbonylmethyl, isopropoxycarbonylmethyl, tert-butoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl, 1-(ethoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 1-(methoxycarbonyl)-1-methylethyl, 1-(ethoxycarbonyl)-1-methylethyl, and 2-(tert-butoxycarbonyl)ethyl.

[0107] In the present invention, "C １ ~C ６ Alkylamino C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-NH-(C １ ~C ６ alkyl)-group, and examples thereof include (methylamino)methyl, (ethylamino)methyl, (isopropylamino)methyl, (tert-butylamino)methyl, 1-(methylamino)ethyl, and 2-(methylamino)ethyl groups.

[0108] In the present invention, "C １ ~C６ Alkoxycarbonylamino C １ ~C ６ Unless otherwise specified, the alkoxy and alkyl moieties of the "alkyl group" have the same meanings as above (C １ ~C ６ alkoxy)-C(O)-NH-(C １ ~C ６ alkyl)-group, and examples thereof include methoxycarbonylaminomethyl, ethoxycarbonylaminomethyl, isopropoxycarbonylaminomethyl, tert-butoxycarbonylaminomethyl, and isobutoxycarbonylaminomethyl groups.

[0109] In the present invention, "C １ ~C ６ Alkylcarbonyl C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-C(O)-(C １ ~C ６ alkyl)-group, and examples thereof include acetylmethyl, propionylmethyl, isopropylcarbonylmethyl, and tert-butylcarbonylmethyl groups.

[0110] In the present invention, "aminosulfonylamino C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the alkyl moiety has the above meaning. ２ N-S (O) ２ -NH-(C １ ~C ６ and the like. Examples of the alkyl group include (sulfamoylamino)methyl, 1-(sulfamoylamino)ethyl, 2-(sulfamoylamino)ethyl, and 3-(sulfamoylamino)propyl.

[0111] In the present invention, "C １ ~C ６ Haloalkylsulfonylamino C １ ~C ６Unless otherwise specified, the haloalkyl and alkyl moieties of the "alkyl group" have the same meanings as above (C １ ~C ６ haloalkyl)-S(O) ２ -NH-(C １ ~C ６ and 3-[(trifluoromethyl)sulfonamido]propyl, for example, [(trifluoromethyl)sulfonamido]methyl, [(2,2,2-trifluoroethyl)sulfonamido]methyl, or 3-[(trifluoromethyl)sulfonamido]propyl.

[0112] In the present invention, "C １ ~C ６ Alkylaminosulfonyl C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkyl group" has the above meaning (C １ ~C ６ alkyl)-NH-S(O) ２ -(C １ ~C ６ and 2-(N-methylsulfamoyl)methyl, (N-ethylsulfamoyl)methyl, (N-n-propylsulfamoyl)methyl, (N-isopropylsulfamoyl)methyl, or 2-(N-methylsulfamoyl)ethyl.

[0113] In the present invention, "C ３ ~C ８ Cycloalkylamino C １ ~C ６ Unless otherwise specified, the cycloalkyl and alkyl moieties of the "alkyl group" have the same meanings as above (C ３ ~C ８ cycloalkyl)-NH-(C １ ~C ６ and represents a (cyclopropylamino)methyl, (cyclobutylamino)methyl, 1-(cyclopropylamino)ethyl, or 2-(cyclopropylamino)ethyl group, for example.

[0114] In the present invention, "C １ ~C ６ Haloalkylamino C１ ~C ６ Unless otherwise specified, the haloalkyl and alkyl moieties of the "alkyl group" have the same meanings as above (C １ ~C ６ haloalkyl)-NH-(C １ ~C ６ alkyl)-group, and examples thereof include (trifluoromethylamino)methyl, (2,2-difluoroethylamino)methyl, (2,2,2-trifluoroethylamino)methyl, 1-(trifluoromethylamino)ethyl, and 2-(trifluoromethylamino)ethyl groups.

[0115] In the present invention, "C １ ~C ６ Alkyl sulfonyl amino C １ ~C ６ Unless otherwise specified, the alkyl group "has the above-mentioned meanings for the alkylcarbonylamino moiety and alkyl moiety (C １ ~C ６ alkyl)-S(O) ２ -NH-(C １ ~C ６ and (2-methylsulfonylamino)ethyl, such as methylsulfonylaminomethyl, ethylsulfonylaminomethyl, isopropylsulfonylaminomethyl, or (2-methylsulfonylamino)ethyl.

[0116] In the present invention, "C １ ~C ６ Alkoxyaminocarbonyl C １ ~C ６ Unless otherwise specified, the alkoxy and alkyl moieties of the "alkyl group" have the same meanings as above (C １ ~C ６ alkoxy)-NH-C(O)-(C １ ~C ６ alkyl)-group, and examples thereof include 2-(methoxyamino)-2-oxoethyl, 2-(ethoxyamino)-2-oxoethyl, and 3-(methoxyamino)-3-oxopropyl groups.

[0117] In the present invention, "C １ ~C ６Unless otherwise specified, the alkoxy portion of the "alkoxyaminocarbonyl group" has the above meaning (C １ ~C ６ alkoxy)-NH-C(O)- group, and examples thereof include methoxycarbamoyl, ethoxycarbamoyl, n-propoxycarbamoyl, n-pentoxycarbamoyl, and isopropoxycarbamoyl groups.

[0118] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylamino group" has the above meaning (C １ ~C ６ alkyl)-NH- group, and examples thereof include methylamino, ethylamino, n-propylamino, and isopropylamino groups.

[0119] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylamino group" has the same meaning as defined above (C １ ~C ６ haloalkyl)-NH- group, and examples thereof include 2-fluoroethylamino, 2,2-difluoroethylamino, 2,2,2-trifluoroethylamino, 2,2,2-trichloroethylamino, pentafluoroethylamino, 3,3,3-trifluoropropylamino, and 1,1,1,3,3,3-hexafluoro-2-propylamino groups.

[0120] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylamino group" has the above meaning (C ３ ~C ８ cycloalkyl)-NH- group, and examples thereof include cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, and cyclooctylamino groups.

[0121] In the present invention, "C １ ~C ６Unless otherwise specified, the alkyl moiety of the "alkylaminocarbonyl group" has the above meaning (C １ ~C ６ alkyl)-NH-C(O)- group, and examples thereof include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, sec-butylaminocarbonyl, tert-butylaminocarbonyl, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 1-ethylpropylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, and n-hexylaminocarbonyl.

[0122] In the present invention, "C ３ ~C ８ Unless otherwise specified, the cycloalkyl moiety of the "cycloalkylaminocarbonyl group" has the above meaning (C ３ ~C ８ cycloalkyl)-NH-C(O)- group, and examples thereof include cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, cycloheptylaminocarbonyl, and cyclooctylaminocarbonyl groups.

[0123] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylaminothiocarbonyl group" has the above meaning (C １ ~C ６alkyl)-NH-C(S)- group, and examples thereof include methylamino(thiocarbonyl), ethylamino(thiocarbonyl), n-propylamino(thiocarbonyl), isopropylamino(thiocarbonyl), n-butylamino(thiocarbonyl), isobutylamino(thiocarbonyl), sec-butylamino(thiocarbonyl), tert-butylamino(thiocarbonyl), n-pentylamino(thiocarbonyl), 1-methylbutylamino(thiocarbonyl), 2-methylbutylamino(thiocarbonyl), 3-methylbutylamino(thiocarbonyl), 1-ethylpropylamino(thiocarbonyl), 1,1-dimethylpropylamino(thiocarbonyl), 1,2-dimethylpropylamino(thiocarbonyl), 2,2-dimethylpropylamino(thiocarbonyl), and n-hexylamino(thiocarbonyl).

[0124] In the present invention, "C １ ~C ６ Alkoxy C １ ~C ６ Unless otherwise specified, the alkoxy and alkyl portions of the "alkylcarbonyl group" have the same meanings as above (C １ ~C ６ alkoxy)-(C １ ~C ６ alkyl)-C(O)- group, and examples thereof include methoxyacetyl, ethoxyacetyl, propoxyacetyl, isopropoxyacetyl, butoxyacetyl, 2-methoxypropionyl, 3-methoxypropionyl, 2-ethoxypropionyl, 3-ethoxypropionyl, 2-methoxybutanoyl, 4-methoxybutanoyl, 2-methoxypentanoyl, and 5-methoxypentanoyl groups.

[0125] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylcarbonylthio group" has the above meaning (C １ ~C ６alkyl)-C(O)-S- group, and examples thereof include methylcarbonylthio, ethylcarbonylthio, propylcarbonylthio, and isopropylcarbonylthio groups.

[0126] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylcarbonylamino group" has the above meaning (C １ ~C ６ alkyl)-C(O)-NH- group, and examples thereof include acetylamino, propionylamino, butyrylamino, and isobutyrylamino groups.

[0127] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkoxy moiety of the "alkoxycarbonylamino group" has the above meaning (C １ ~C ６ It represents a (alkoxy)-C(O)-NH- group, and examples thereof include methoxycarbonylamino, ethoxycarbonylamino, isopropoxycarbonylamino, tert-butoxycarbonylamino, and isobutoxycarbonylamino groups.

[0128] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl portion of the "alkylaminocarbonylamino group" has the above meaning (C １ ~C ６ alkyl)-NH-C(O)-NH- group, and examples thereof include methylaminocarbonylamino, ethylaminocarbonylamino, n-propylaminocarbonylamino, isopropylaminocarbonylamino, and tert-butylaminocarbonylamino groups.

[0129] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylsulfonylamino group" has the above meaning (C １ ~C ６ alkyl)-S(O) ２It represents an —NH— group, and examples thereof include methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, isopropylsulfonylamino, and tert-butylsulfonylamino groups.

[0130] In the present invention, "C １ ~C ６ Unless otherwise specified, the haloalkyl moiety of the "haloalkylsulfonylamino group" has the same meaning as above (C １ ~C ６ haloalkyl)-S(O) ２ It represents an —NH— group, and examples thereof include fluoromethylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, chloromethylsulfonylamino, trichloromethylsulfonylamino, 2,2,2-trifluoroethylsulfonylamino, 2,2-difluoroethylsulfonylamino, and 3,3,3-trifluoropropylsulfonylamino groups.

[0131] In the present invention, "C １ ~C ６ Unless otherwise specified, the alkyl moiety of the "alkylaminosulfonylamino group" has the above meaning (C １ ~C ６ alkyl)-NH-S(O) ２ It represents an —NH— group, and examples thereof include methylaminosulfonylamino, ethylaminosulfonylamino, n-propylaminosulfonylamino, isopropylaminosulfonylamino, and tert-butylaminosulfonylamino groups.

[0132] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylamino group" refers to a (5- to 12-membered heteroaryl)-NH- group in which the heteroaryl moiety has the above-mentioned meaning, and examples thereof include pyridylamino, pyrimidinylamino, pyrazinylamino, pyridazinylamino, triazinylamino, thienylamino, furanylamino, pyrrolylamino, pyrazolylamino, thiazolylamino, isothiazolylamino, oxazolylamino, isoxazolylamino, imidazolylamino, triazolylamino, thiadiazolylamino, oxadiazolylamino, and tetrazolylamino groups.

[0133] In the present invention, "C ６ ~C １２ Aryl C １ ~C ６ Unless otherwise specified, the aryl and alkyl portions of the "alkyl group" have the same meanings as above (C ６ ~C １２ aryl)-(C １ ~C ６ alkyl)-group, and examples thereof include benzyl, 1-phenylethyl, 2-phenylethyl, 2-phenylpropyl, 2-phenylbutyl, 1-phenylpentyl, naphthalen-1-ylmethyl, and naphthalen-2-ylmethyl groups.

[0134] In the present invention, "5- to 12-membered heteroaryl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the heteroaryl and alkyl moieties have the same meanings as above (5- to 12-membered heteroaryl)-(C １ ~C ６alkyl)-group, for example, pyridylmethyl, pyrimidinylmethyl, pyrazinylmethyl, pyridazinylmethyl, triazinylmethyl, thienylmethyl, furanylmethyl, pyrrolylmethyl, pyrazolylmethyl, thiazolylmethyl, isothiazolylmethyl, oxazolylmethyl, isoxazolylmethyl, imidazolylmethyl, triazolylmethyl, thiadiazolylmethyl, oxadiazolylmethyl, tetrazolylmethyl, indolylmethyl, benzimidazolylmethyl, indazolylmethyl, benzotriazolylmethyl, isoquinolinylmethyl, quinolinylmethyl, benzothiazolylmethyl, benzofuranylmethyl Examples of such groups include 1-pyridyl, benzothienylmethyl, benzisoxazolylmethyl, pyrazolopyridylmethyl, pyrazolopyrimidinylmethyl, pyrrolopyridylmethyl, triazolopyridylmethyl, triazolopyrimidinylmethyl, quinazolinylmethyl, quinoxalinylmethyl, cinnolinylmethyl, 1-pyridylethyl, 2-pyridyl-2-propyl, 1-pyrazolylethyl, 2-pyrazolyl-2-propyl, 1-thiazolylethyl, 2-thiazolyl-2-propyl, 1-thiadiazolylethyl, 2-thiadiazolyl-2-propyl, 1-oxadiazolylethyl, and 2-thiadiazolyl-2-propyl.

[0135] In the present invention, "3- to 6-membered heterocyclyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the heterocyclyl and alkyl moieties have the same meanings as above (3- to 6-membered heterocyclyl)-(C １ ~C ６ alkyl)-group, and examples thereof include aziridinylmethyl, oxiranylmethyl, oxetanylmethyl, thietanylmethyl, tetrahydrofuranylmethyl, tetrahydropyranylmethyl, azetidinylmethyl, pyrrolidinylmethyl, piperidinylmethyl, piperazinylmethyl, dihydroisoxazolylmethyl, dioxaborolanylmethyl, dioxolanylmethyl, dioxanylmethyl, and morpholinylmethyl groups.

[0136] In the present invention, "C ６ ~C １２Unless otherwise specified, the aryl moiety of the "aryloxy group" has the above meaning (C ６ ~C １２ aryl)-O- group, and examples thereof include phenyloxy, 2-biphenyloxy, 4-biphenyloxy, naphthalen-1-yloxy, and naphthalen-2-yloxy groups.

[0137] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroaryloxy group" refers to a (5- to 12-membered heteroaryl)-O- group in which the heteroaryl moiety has the above-mentioned meaning, and examples thereof include (pyridin-2-yl)oxy, (pyridin-3-yl)oxy, (pyridin-4-yl)oxy, (pyrimidin-2-yl)oxy, (pyrimidin-4-yl)oxy, (pyrimidin-5-yl)oxy, (pyridazin-3-yl)oxy, (pyridazin-4-yl)oxy, (pyrazin-2-yl)oxy, (1,3,5-triazinin-2-yl)oxy, (thiazol-2-yl)oxy, (thiazol-4-yl)oxy, (thiazol-5-yl)oxy, (pyrazol-1-yl)oxy, (pyrazol-3-yl)oxy, (pyrazol-4-yl)oxy, and (pyrazol-5-yl)oxy.

[0138] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclyloxy group" refers to a (3- to 6-membered heterocyclyl)-O- group in which the heterocyclyl moiety has the above-mentioned meaning, and examples thereof include aziridinyloxy, oxiranyloxy, oxetanyloxy, thietanyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, azetidinyloxy, pyrrolidinyloxy, piperidinyloxy, piperazinyloxy, dihydroisoxazolyloxy, dioxaborolanyloxy, dioxolanyloxy, dioxanyloxy, and morpholinyloxy groups.

[0139] In the present invention, "C ６ ~C １２ Aryloxy C １ ~C ６ Unless otherwise specified, the aryloxy moiety and alkyl moiety of the "alkyl group" have the same meaning as above (C６ ~C １２ aryloxy)-(C １ ~C ６ alkyl)-group, and examples thereof include phenoxymethyl, 1-phenoxyethyl, 2-phenoxyethyl, (naphthalen-1-yloxy)methyl, and (naphthalen-2-yloxy)methyl groups.

[0140] In the present invention, "5- to 12-membered heteroaryloxy C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the heteroaryloxy moiety and alkyl moiety have the same meaning as above (5- to 12-membered heteroaryloxy)-(C １ ~C ６ alkyl)-group, and examples thereof include (pyridin-2-yloxy)methyl, (pyridin-3-yloxy)methyl, (pyridin-4-yloxy)methyl, (pyrimidin-2-yloxy)methyl, (pyrimidin-4-yloxy)methyl, (pyrimidin-5-yloxy)methyl, (pyridazin-3-yloxy)methyl, (pyridazin-4-yloxy)methyl, (pyrazin-2-yloxy)methyl, (1,3,5-triazinin-2-yloxy)methyl, (thiazol-2-yloxy)methyl, (thiazol-4-yloxy)methyl, (thiazol-5-yloxy)methyl, (pyrazol-1-yloxy)methyl, (pyrazol-3-yloxy)methyl, 1-(pyridin-3-yloxy)ethyl, and 2-(pyridin-3-yloxy)ethyl groups.

[0141] In the present invention, "3- to 6-membered heterocyclyloxy C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the heterocyclyloxy moiety has the same meaning as above (3- to 6-membered heterocyclyl)-(C １ ~C ６alkyl)-group, and examples thereof include (aziridinyloxy)methyl, (oxiranyloxy)methyl, (oxetanyloxy)methyl, (thietanyloxy)methyl, (tetrahydrofuranyloxy)methyl, (tetrahydropyranyloxy)methyl, (azetidinyloxy)methyl, (pyrrolidinyloxy)methyl, (piperidinyloxy)methyl, (piperazinyloxy)methyl, (dihydroisoxazolyloxy)methyl, (dioxaborolanyloxy)methyl, (dioxolanyloxy)methyl, (dioxanyloxy)methyl, and (morpholinyloxy)methyl groups.

[0142] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylthio group" has the above meaning (C ６ ~C １２ aryl)-S- group, and examples thereof include phenylthio, 2-biphenylthio, 4-biphenylthio, naphthalen-1-ylthio, and naphthalen-2-ylthio groups.

[0143] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylsulfinyl group" has the above meaning (C ６ ~C １２ aryl)-S(O)- group, and examples thereof include phenylsulfinyl, 2-biphenylsulfinyl, 4-biphenylsulfinyl, naphthalen-1-ylsulfinyl, and naphthalen-2-ylsulfinyl groups.

[0144] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylsulfonyl group" has the above meaning (C ６ ~C １２ aryl)-S(O) ２ - group, and examples thereof include phenylsulfonyl, 2-biphenylsulfonyl, 4-biphenylsulfonyl, naphthalen-1-ylsulfonyl, and naphthalen-2-ylsulfonyl groups.

[0145] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylthio group" refers to a (5- to 12-membered heteroaryl)-S- group in which the heteroaryl moiety has the above meaning, and examples thereof include pyridylthio, pyrimidinylthio, pyrazinylthio, pyridazinylthio, triazinylthio, thienylthio, furanylthio, pyrrolylthio, pyrazolylthio, thiazolylthio, isothiazolylthio, oxazolylthio, isoxazolylthio, imidazolylthio, triazolylthio, thiadiazolylthio, and oxazolylthio. Examples of groups include azolylthio, tetrazolylthio, indolylthio, benzimidazolylthio, indazolylthio, benzotriazolylthio, isoquinolinylthio, quinolinylthio, benzothiazolylthio, benzofuranylthio, benzothienylthio, benzisoxazolylthio, pyrazolopyridylthio, pyrazolopyrimidinylthio, pyrrolopyridylthio, triazolopyridylthio, triazolopyrimidinylthio, quinazolinylthio, quinoxalinylthio, and cinnolinylthio.

[0146] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylsulfinyl group" refers to a (5- to 12-membered heteroaryl)-S(O)- group in which the heteroaryl moiety has the above meaning, and examples thereof include pyridylsulfinyl, pyrimidinylsulfinyl, pyrazinylsulfinyl, pyridazinylsulfinyl, triazinylsulfinyl, thienylsulfinyl, furanylsulfinyl, pyrrolylsulfinyl, pyrazolylsulfinyl, thiazolylsulfinyl, isothiazolylsulfinyl, oxazolylsulfinyl, isoxazolylsulfinyl, imidazolylsulfinyl, triazolylsulfinyl, thiadiazolylsulfinyl, and oxadiazolyl. Examples of such groups include sulfinyl, tetrazolylsulfinyl, indolylsulfinyl, benzimidazolylsulfinyl, indazolylsulfinyl, benzotriazolylsulfinyl, isoquinolinylsulfinyl, quinolinylsulfinyl, benzothiazolylsulfinyl, benzofuranylsulfinyl, benzothienylsulfinyl, benzisoxazolylsulfinyl, pyrazolopyridylsulfinyl, pyrazolopyrimidinylsulfinyl, pyrrolopyridylsulfinyl, triazolopyridylsulfinyl, triazolopyrimidinylsulfinyl, quinazolinylsulfinyl, quinoxalinylsulfinyl, and cinnolinylsulfinyl.

[0147] In the present invention, unless otherwise specified, the "5- to 12-membered heteroarylsulfonyl group" refers to a (5- to 12-membered heteroaryl)-S(O) group in which the heteroaryl moiety has the above-mentioned meaning. ２- group, for example, pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl, pyridazinylsulfonyl, triazinylsulfonyl, thienylsulfonyl, furanylsulfonyl, pyrrolylsulfonyl, pyrazolylsulfonyl, thiazolylsulfonyl, isothiazolylsulfonyl, oxazolylsulfonyl, isoxazolylsulfonyl, imidazolylsulfonyl, triazolylsulfonyl, thiadiazolylsulfonyl, oxadiazolylsulfonyl, tetrazolylsulfonyl, indolylsulfonyl, benzimidazolyl Examples of such groups include sulfonyl, indazolylsulfonyl, benzotriazolylsulfonyl, isoquinolinylsulfonyl, quinolinylsulfonyl, benzothiazolylsulfonyl, benzofuranylsulfonyl, benzothienylsulfonyl, benzisoxazolylsulfonyl, pyrazolopyridylsulfonyl, pyrazolopyrimidinylsulfonyl, pyrrolopyridylsulfonyl, triazolopyridylsulfonyl, triazolopyrimidinylsulfonyl, quinazolinylsulfonyl, quinoxalinylsulfonyl, and cinnolinylsulfonyl.

[0148] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclylthio group" refers to a (3- to 6-membered heterocyclyl)-S- group in which the heterocyclyl moiety has the above-mentioned meaning, and examples thereof include aziridinylthio, oxiranylthio, oxetanylthio, thietanylthio, tetrahydrofuranylthio, tetrahydropyranylthio, azetidinylthio, pyrrolidinylthio, piperidinylthio, piperazinylthio, dihydroisoxazolylthio, dioxaborolanylthio, dioxolanylthio, dioxanylthio, and morpholinylthio groups.

[0149] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclylsulfinyl group" refers to a (3- to 6-membered heterocyclyl)-S(O)- group in which the heterocyclyl moiety has the above-mentioned meaning, and examples thereof include aziridinylsulfinyl, oxiranylsulfinyl, oxetanylsulfinyl, thietanylsulfinyl, tetrahydrofuranylsulfinyl, tetrahydropyranylsulfinyl, azetidinylsulfinyl, pyrrolidinylsulfinyl, piperidinylsulfinyl, piperazinylsulfinyl, dihydroisoxazolylsulfinyl, dioxaborolanylsulfinyl, dioxolanylsulfinyl, dioxanylsulfinyl, and morpholinylsulfinyl groups.

[0150] In the present invention, unless otherwise specified, the "3- to 6-membered heterocyclylsulfonyl group" refers to a (3- to 6-membered heterocyclyl)-S(O) group in which the heterocyclyl moiety has the above-mentioned meaning. ２ - group, and examples thereof include aziridinylsulfonyl, oxiranylsulfonyl, oxetanylsulfonyl, thietanylsulfonyl, tetrahydrofuranylsulfonyl, tetrahydropyranylsulfonyl, azetidinylsulfonyl, pyrrolidinylsulfonyl, piperidinylsulfonyl, piperazinylsulfonyl, dihydroisoxazolylsulfonyl, dioxaborolanylsulfonyl, dioxolanylsulfonyl, dioxanylsulfonyl, and morpholinylsulfonyl groups.

[0151] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylcarbonyl group" has the above meaning (C ６ ~C １２ aryl)-C(O)- group, and examples thereof include benzoyl, 2-biphenylcarbonyl, 4-biphenylcarbonyl, naphthalen-1-ylcarbonyl, and naphthalen-2-ylcarbonyl groups.

[0152] In the present invention, "C ６ ~C １２Unless otherwise specified, the aryloxycarbonyl group has the above-mentioned meanings for the aryloxy moiety and the carbonyl moiety (C ６ ~C １２ aryloxy)-C(O)- group, and examples thereof include phenoxycarbonyl, 2-biphenyloxycarbonyl, 4-biphenyloxycarbonyl, naphthalen-1-yloxycarbonyl, and naphthalen-2-yloxycarbonyl groups.

[0153] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylcarbonyl group" refers to a (5- to 12-membered heteroaryl)-C(O)- group in which the heteroaryl moiety has the above meaning, and examples thereof include pyridylcarbonyl, pyrimidinylcarbonyl, pyrazinylcarbonyl, pyridazinylcarbonyl, triazinylcarbonyl, thienylcarbonyl, furanylcarbonyl, pyrrolylcarbonyl, pyrazolylcarbonyl, thiazolylcarbonyl, isothiazolylcarbonyl, oxazolylcarbonyl, isoxazolylcarbonyl, imidazolylcarbonyl, triazolylcarbonyl, thiadiazolylcarbonyl, oxadiazolylcarbonyl, and the like. Examples of such groups include arylcarbonyl, tetrazolylcarbonyl, indolylcarbonyl, benzimidazolylcarbonyl, indazolylcarbonyl, benzotriazolylcarbonyl, isoquinolinylcarbonyl, quinolinylcarbonyl, benzothiazolylcarbonyl, benzofuranylcarbonyl, benzothienylcarbonyl, benzisoxazolylcarbonyl, pyrazolopyridylcarbonyl, pyrazolopyrimidinylcarbonyl, pyrrolopyridylcarbonyl, triazolopyridylcarbonyl, triazolopyrimidinylcarbonyl, quinazolinylcarbonyl, quinoxalinylcarbonyl, and cinnolinylcarbonyl.

[0154] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroaryloxycarbonyl group" refers to a (5- to 12-membered heteroaryloxy)-C(O)- group in which the heteroaryl moiety has the above meaning, and examples thereof include pyridyloxycarbonyl, pyrimidinyloxycarbonyl, pyrazinyloxycarbonyl, pyridazinyloxycarbonyl, triazinyloxycarbonyl, thienyloxycarbonyl, furanyloxycarbonyl, pyrrolyloxycarbonyl, pyrazolyloxycarbonyl, thiazolyloxycarbonyl, isothiazolyloxycarbonyl, oxazolyloxycarbonyl, isoxazolyloxycarbonyl, imidazolyloxycarbonyl, triazolyloxycarbonyl, thiadiazolyloxycarbonyl, oxadiazolyloxycarbonyl, and the like. Examples of such groups include aryloxycarbonyl, tetrazolyloxycarbonyl, indolyloxycarbonyl, benzimidazolyloxycarbonyl, indazolyloxycarbonyl, benzotriazolyloxycarbonyl, isoquinolinyloxycarbonyl, quinolinyloxycarbonyl, benzothiazolyloxycarbonyl, benzofuranyloxycarbonyl, benzothienyloxycarbonyl, benzisoxazolyloxycarbonyl, pyrazolopyridyloxycarbonyl, pyrazolopyrimidinyloxycarbonyl, pyrrolopyridyloxycarbonyl, triazolopyridyloxycarbonyl, triazolopyrimidinyloxycarbonyl, quinazolinyloxycarbonyl, quinoxalinyloxycarbonyl, and cinnolinyloxycarbonyl.

[0155] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclylcarbonyl group" refers to a (3- to 6-membered heterocyclyl)-C(O)- group in which the heterocyclyl moiety has the above-mentioned meaning, and examples thereof include aziridinylcarbonyl, oxiranylcarbonyl, oxetanylcarbonyl, thietanylcarbonyl, tetrahydrofuranylcarbonyl, tetrahydropyranylcarbonyl, azetidinylcarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl, piperazinylcarbonyl, dihydroisoxazolylcarbonyl, dioxaborolanylcarbonyl, dioxolanylcarbonyl, dioxanylcarbonyl, and morpholinylcarbonyl.

[0156] In the present invention, "C ６ ~C １２ Aryl C １ ~C ６ Unless otherwise specified, the aryl and alkyl portions of the "alkylcarbonyl group" have the same meanings as above (C ６ ~C １２ aryl)-(C １ ~C ６ (alkyl)-C(O)- group, and examples thereof include benzylcarbonyl, (1-phenylethyl)carbonyl, (2-phenylethyl)carbonyl, (naphthalen-1-ylmethyl)carbonyl, and (naphthalen-2-ylmethyl)carbonyl groups.

[0157] In the present invention, "5- to 12-membered heteroaryl C １ ~C ６ Unless otherwise specified, the term "alkylcarbonyl group" refers to a group in which the heteroaryl and alkyl moieties have the same meanings as above (5- to 12-membered heteroaryl)-(C １ ~C ６ alkyl)-C(O)- group, and examples thereof include (pyridylmethyl)carbonyl, (pyrimidinylmethyl)carbonyl, (pyrazinylmethyl)carbonyl, (pyridazinylmethyl)carbonyl, (triazinylmethyl)carbonyl, (thienylmethyl)carbonyl, (furanylmethyl)carbonyl, (pyrrolylmethyl)carbonyl, (pyrazolylmethyl)carbonyl, (thiazolylmethyl)carbonyl, (isothiazolylmethyl)carbonyl, (oxazolylmethyl)carbonyl, (isoxazolylmethyl)carbonyl, (imidazolylmethyl)carbonyl, (triazolylmethyl)carbonyl, (thiadiazolylmethyl)carbonyl, (oxadiazolylmethyl)carbonyl, (tetrazolylmethyl)carbonyl, (quinazolinylmethyl)carbonyl, and (quinoxalinylmethyl)carbonyl groups.

[0158] In the present invention, "3- to 6-membered heterocyclyl C １ ~C ６Unless otherwise specified, the term "alkylcarbonyl group" refers to a (3- to 6-membered heterocyclyl)-(C １ ~C ６ alkyl)-C(O)- group, and examples thereof include (oxiranylmethyl)carbonyl, (oxetanylmethyl)carbonyl, (thietanylmethyl)carbonyl, (tetrahydrofuranylmethyl)carbonyl, (tetrahydropyranylmethyl)carbonyl, (azetidinylmethyl)carbonyl, (pyrrolidinylmethyl)carbonyl, (piperidinylmethyl)carbonyl, (piperazinylmethyl)carbonyl, (dioxolanylmethyl)carbonyl, (dioxanylmethyl)carbonyl, and (morpholinylmethyl)carbonyl groups.

[0159] In the present invention, "C ６ ~C １２ Unless otherwise specified, the aryl moiety of the "arylaminocarbonyl group" has the above meaning (C ６ ~C １２ (aryl)-NH-C(O)- group, and examples thereof include (phenylamino)carbonyl, (naphthalen-1-ylamino)carbonyl, and (naphthalen-2-ylamino)carbonyl groups.

[0160] In the present invention, unless otherwise specified, the term "5- to 12-membered heteroarylaminocarbonyl group" refers to a (5- to 12-membered heteroaryl)-NH-C(O)- group in which the heteroaryl moiety has the above-mentioned meaning, and examples thereof include (pyridylamino)carbonyl, (pyrimidinylamino)carbonyl, (pyrazinylamino)carbonyl, (pyridazinylamino)carbonyl, (triazinylamino)carbonyl, (thienylamino)carbonyl, (furanylamino)carbonyl, (pyrrolylamino)carbonyl, (pyrazolylamino)carbonyl, (thiazolylamino)carbonyl, (isothiazolylamino)carbonyl, (oxazolylamino)carbonyl, (isoxazolylamino)carbonyl, (imidazolylamino)carbonyl, (triazolylamino)carbonyl, (thiadiazolylamino)carbonyl, (oxadiazolylamino)carbonyl, and (tetrazolylamino)carbonyl groups.

[0161] In the present invention, unless otherwise specified, the term "3- to 6-membered heterocyclylaminocarbonyl group" refers to a (3- to 6-membered heterocyclyl)-NH-C(O)- group in which the heteroaryl moiety has the above-mentioned meaning, and examples thereof include (oxiranylamino)carbonyl, (oxetanylamino)carbonyl, (thietanylamino)carbonyl, (tetrahydrofuranylamino)carbonyl, (tetrahydropyranylamino)carbonyl, (azetidinylamino)carbonyl, (pyrrolidinylamino)carbonyl, (piperidinylamino)carbonyl, (dioxolanylamino)carbonyl, (dioxanylamino)carbonyl, and (morpholinylamino)carbonyl groups.

[0162] In the present invention, "C ６ ~C １２ Arylaminocarbonyl C １ ~C ６ Unless otherwise specified, the aryl and alkyl moieties of the "alkyl group" have the same meanings as above (C ６ ~C １２ aryl)-NH-C(O)-(C １ ~C ６and 2-(phenylaminocarbonyl)methyl, (naphthalen-1-ylaminocarbonyl)methyl, (naphthalen-2-ylaminocarbonyl)methyl, or 2-(phenylaminocarbonyl)ethyl.

[0163] In the present invention, "C ６ ~C １２ Arylcarbonyl C １ ~C ６ Unless otherwise specified, the aryl and alkyl moieties of the "alkyl group" have the same meanings as above (C ６ ~C １２ aryl)-C(O)-(C １ ~C ６ and 2-(phenylcarbonyl)methyl, (naphthalen-1-ylcarbonyl)methyl, (naphthalen-2-ylcarbonyl)methyl, or 2-(phenylcarbonyl)ethyl.

[0164] In the present invention, "5- to 12-membered heteroarylcarbonyl C １ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the heteroaryl and alkyl moieties have the same meanings as above, such as (5- to 12-membered heteroaryl)-C(O)-(C １ ~C ６ alkyl)-group, and examples thereof include (pyridylcarbonyl)methyl, (pyrimidinylcarbonyl)methyl, (pyrazinylcarbonyl)methyl, (pyridazinylcarbonyl)methyl, (triazinylcarbonyl)methyl, (thienylcarbonyl)methyl, (furanylcarbonyl)methyl, (pyrrolylcarbonyl)methyl, (pyrazolylcarbonyl)methyl, (thiazolylcarbonyl)methyl, (isothiazolylcarbonyl)methyl, (oxazolylcarbonyl)methyl, (isoxazolylcarbonyl)methyl, (imidazolylcarbonyl)methyl, (triazolylcarbonyl)methyl, (thiadiazolylcarbonyl)methyl, (oxadiazolylcarbonyl)methyl, and (tetrazolylcarbonyl)methyl groups.

[0165] In the present invention, "3- to 6-membered heterocyclylcarbonyl C１ ~C ６ Unless otherwise specified, the term "alkyl group" refers to a group in which the heterocyclyl and alkyl moieties have the same meanings as above (3- to 6-membered heterocyclyl)-C(O)-(C １ ~C ６ alkyl)-group, and examples thereof include (oxiranylcarbonyl)methyl, (oxetanylcarbonyl)methyl, (thietanylcarbonyl)methyl, (tetrahydrofuranylcarbonyl)methyl, (tetrahydropyranylcarbonyl)methyl, (azetidinylcarbonyl)methyl, (pyrrolidinylcarbonyl)methyl, (piperidinylcarbonyl)methyl, (piperazinylcarbonyl), (dioxolanylcarbonyl)methyl, (dioxanylcarbonyl)methyl, and (morpholinylcarbonyl)methyl groups.

[0166] In the present invention, "optionally substituted with one or more substituents selected from substituent group α" means unsubstituted or "optionally substituted with one or more substituents selected from substituent group α". When substituted with two or more substituents, the two or more substituents selected from substituent group α may be the same or different, and may be a hydrogen atom, a halogen atom, a hydroxy group, a mercapto group, an amino group, a cyano group, a nitro group, a C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a halocycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６ Alkoxy group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ haloalkyl group, and cyano group), C ２ ~C ６ Alkenyloxy group, C ２ ~C ６ Alkynyloxy group, tri(C １ ~C ６ alkyl)silyloxy group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C ６ ~C １２ an aryl group (the aryl group is not a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ alkylamino group (the amino group may be substituted with one or more substituents selected from the substituent group γ), cyano group), 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ), a cyano group), an oxo group, or —C(═NR ｍ ) R ｎ The group may be substituted with one or more chemically acceptable substituents selected from the group.

[0167] In the present invention, "optionally substituted with one or more substituents selected from the substituent group β" means unsubstituted or "optionally substituted with one or more substituents selected from the substituent group β". When substituted with two or more substituents, the two or more substituents selected from the substituent group β may be the same or different, and may be a hydrogen atom, a halogen atom, a hydroxy group, an amino group, a cyano group, a C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C １ ~C ６ haloalkyl groups), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy-C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ); ６ ~C １２ an aryl group (the aryl group is not a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６alkylamino group (the amino group may be substituted with one or more substituents selected from the substituent group γ), cyano group), 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ) or a cyano group), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ It may be substituted with one or more chemically acceptable substituents selected from an alkylamino group (the amino group may be substituted with a substituent selected from substituent group γ), and a cyano group).

[0168] In the present invention, "optionally substituted with one or more substituents selected from the substituent group γ" means unsubstituted or "optionally substituted with one or more substituents selected from the substituent group γ". When substituted with two or more substituents, the two or more substituents selected from the substituent group γ may be the same or different, and may be a hydrogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C１ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ haloalkylcarbonyl group, or C １ ~C ６ It may be substituted with one or more chemically acceptable substituents selected from alkoxycarbonyl groups.

[0169] In the present invention, "-N=C(C １ ~C ６ alkyl group) ２ " means that, unless otherwise specified, the carbon atom bonded to the nitrogen atom is the same as the above C １ ~C ６ represents that the group is substituted by two arbitrary substituents selected from alkyl groups, and two C １ ~C ６ The alkyl groups may be the same or different from each other.

[0170] In the present invention, "R ２ and R ３ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 5- or 6-membered ring together with 0 to 1 atom or atomic group selected from, and the 5- or 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ The term "optionally substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group" includes, but is not limited to, the following:

[0171]

[0172] In the present invention, "R ａ and R ｂare mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a nitrogen-containing 4- to 6-membered ring together with 0 to 1 atom or atomic group selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ The term "optionally substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group" includes, but is not limited to, the following:

[0173]

[0174] In the present invention, "R ｄ and R ｅ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 3- to 6-membered ring together with 0 to 2 atoms or atomic groups selected from, and the 3- to 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ The term "optionally substituted with one or more chemically acceptable substituents selected from an alkoxy group and an oxo group" includes, but is not limited to, the following:

[0175]

[0176] In the present invention, "R ｉ and R ｋ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a nitrogen-containing 4- to 6-membered ring together with 0 to 1 atom or atomic group selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C１ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from substituent group γ), C １ ~C ６ Examples of "optionally substituted by one or more chemically acceptable substituents selected from an alkylcarbonylamino group (the amino group may be substituted by a substituent selected from substituent group γ), or an oxo group" include, but are not limited to, the following:

[0177]

[0178] In the present invention, "R ｏ and R ｐ may be bonded to each other to form a 5- or 6-membered ring together with 0 to 2 atoms or atomic groups selected from carbon atoms, oxygen atoms, and sulfur atoms (the sulfur atoms may be oxidized with 1 or 2 oxygen atoms), and the 5- or 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ The term "optionally substituted with one or more chemically acceptable substituents selected from an alkoxy group, an oxo group, or an oxo group" includes, but is not limited to, the following:

[0179]

[0180] In the present invention, the salt refers to a salt formed of a hydroxyl group, a carboxyl group, an amino group, a nitrogen atom of a pyridine ring, or the like, present in the structure of the compound of the present invention represented by general formula [I], and a metal or an organic base, or a salt formed of a mineral acid or an organic acid. Examples of the metal include alkali metals such as sodium or potassium, or alkaline earth metals such as magnesium or calcium. Examples of the organic base include triethylamine or diisopropylamine. Examples of the mineral acid include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, sulfuric acid, and the like. Examples of the organic acid include formic acid, acetic acid, lactic acid, ascorbic acid, succinic acid, fumaric acid, maleic acid, oxalic acid, citric acid, benzoic acid, salicylic acid, tartaric acid, methanesulfonic acid, 4-toluenesulfonic acid, trifluoromethanesulfonic acid, and the like.

[0181] Next, representative examples of compounds included in the nicotinamide derivatives of the present invention represented by general formula [I] are shown in Tables 1 to 88. However, the compounds included in the present invention are not limited to these. The compound numbers in the tables will be referred to in the following description.

[0182] Representative examples of compounds that can be used as intermediates for producing the nicotinamide derivatives of the present invention are shown in Tables 89 to 104. However, synthetic intermediates for nicotinamide derivatives are not limited to these. The compound numbers in the tables will be referenced in the following description.

[0183] Compounds encompassed by the nicotinamide derivatives of the present invention may have E- and Z-configurations depending on the type of substituent bonded to the carbon-nitrogen or carbon-carbon double bond, and the present invention encompasses mixtures containing these E- and Z-configurations in any ratio.

[0184] The compounds encompassed by the nicotinamide derivatives of the present invention may have optical isomers due to the presence of one or more asymmetric carbon atoms and asymmetric sulfur atoms, but the present invention encompasses all optically active compounds, racemates, and diastereomers.

[0185] The compounds included in the nicotinamide derivatives of the present invention may have tautomers depending on the type of substituent, and the present invention includes mixtures containing these in any ratio. In addition, the naming of the compounds does not exclude any tautomers, and examples thereof include, but are not limited to, the following:

[0186]

[0187] The following symbols in the tables in this specification represent, for example, the corresponding groups as follows: Me: methyl; Et: ethyl; Pr-n: n-propyl; Pr-i: isopropyl; Bu-n: n-butyl; Bu-i: isobutyl; Bu-s: sec-butyl; Bu-t: tert-butyl; Pen-n: n-pentyl; Pen-i: isopentyl; Pen-s: sec-pentyl; Pen-neo: neopentyl; Hex-n: n-hexyl; CH ２ F: fluoromethyl; CHF ２ : difluoromethyl; CF ３ : trifluoromethyl; CH ２ CF ３: 2,2,2-trifluoroethyl; Pr-c: cyclopropyl; Bu-c: cyclobutyl; Pen-c: cyclopentyl; Hex-c: cyclohexyl; C(O): carbonyl; C(S): thiocarbonyl; S(O): sulfinyl; S(O) ２ : sulfonyl; Ph: phenyl; Ac: acetyl; CN: cyano; OH: hydroxy; NO: ２ : nitro; CH ２ Ph(4-OMe) : 4-methoxy-benzyl; Boc : tert-butoxycarbonyl; Npht : 1,3-dioxoisoindolin-2-yl;

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292] On the other hand, the compound of the present invention represented by general formula [I] can be produced according to the production methods shown below, but is not limited to these methods. Hereinafter, for example, "a compound represented by general formula [I-1]" and "compound [I-1]" are synonymous (meaning the same).

[0293] In the structure [I], [III] or [IV] described in the production method, the skeleton of [VI] shown below represents either L-1', L-2' or L-3'.

[0294]

[0295] (In the formula, R ５ , R ６ , R ７ , R ９ , R ｘ , R ｙ , R ｚ , A １ , A ２ and Y have the same meaning as above.

[0296] <Production Method 1> Among the compounds of the present invention, the compound represented by general formula [I-1] can be produced using the compound represented by general formula [II-1] according to the method consisting of the reaction scheme exemplified below.

[0297]

[0298] (In the reaction formula, X ２ is a halogen atom, OC(O)OR １０ , a leaving group such as a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group, or a p-toluenesulfonyloxy group; R １０ is C １ ~C ６ represents an alkyl group, and R １ , R ２ , R ３ , R ４ , R ７ , R ８ , R ９ , Y, and Q have the same meanings as above.)

[0299] That is, the compound represented by general formula [I-1] can be produced by (Step 1-1) hydrolyzing compound [II-1] in the presence of a suitable acid or base in a suitable solvent to give compound [II-2], then (Step 1-2) converting compound [II-2] into an active derivative such as an acid halide or mixed acid anhydride, compound [II-3], in a suitable solvent with or without a suitable catalyst, and (Step 1-3) reacting compound [III-1] with compound [III-1] in a suitable solvent with or without a suitable base and with or without a suitable catalyst. Furthermore, the compound represented by general formula [I-1] can also be produced by (Step 1-4) reacting compound [II-2] with compound [III-1] in a suitable solvent with or without a suitable condensing agent and a suitable additive, with or without a suitable catalyst, and with or without a suitable base.

[0300] (Step 1-1) Examples of acids that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, etc.; carboxylic acids such as acetic acid, trifluoroacetic acid, etc.; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, etc. The amount of the acid used can be appropriately selected from a range of 1.0 to 1,000 mol, preferably 1.0 to 100 mol, per 1 mol of compound [II-1].

[0301] Examples of the base that can be used in this reaction include inorganic bases such as alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides, such as calcium hydroxide, magnesium hydroxide, and barium hydroxide; alkali metal carbonates, such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; and alkali metal bicarbonates, such as sodium hydrogencarbonate and potassium hydrogencarbonate. The amount of the base used may be appropriately selected from the range of 0.1 to 50 mol per mol of compound [II-1], and is preferably 0.5 to 20 mol.

[0302] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, methyl tert-butyl ether, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, and 2-propanol; nitriles such as acetonitrile and propionitrile; ketones such as acetone and methyl ethyl ketone; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per mole of Compound [II-1].

[0303] The reaction temperature for this reaction may be selected from the range of temperatures usually from -30°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 150°C.

[0304] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0305] After the reaction is complete, the reaction mixture is poured into water for neutralization, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [II-2]. The isolated compound [II-2] can be further purified, if necessary, by column chromatography, recrystallization, or the like.

[0306] (Step 1-2) Examples of the reagent used in this reaction to convert compound [II-2] to compound [II-3] include thionyl chloride, oxalyl chloride, phosphoryl chloride, isobutyl chlorocarbonate, methanesulfonyl chloride, trifluoromethanesulfonyl chloride, p-toluenesulfonyl chloride, etc. The amount of the reagent used to convert compound [II-3] may be appropriately selected from a range of 0.5 to 30 mol, preferably 0.5 to 6.0 mol, per 1 mol of compound [II-2].

[0307] Examples of the catalyst that can be used in this reaction include N,N-dimethylformamide, dimethylacetamide, N-methylpyrrolidone, 1,3-dimethylimidazolidinone, tetramethylurea, tetraethylurea, tetrabutylurea, etc. The amount of the catalyst used may be appropriately selected from the range of 0.01 to 1.0 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [II-2].

[0308] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; and mixed solvents thereof. The amount of the solvent used is 0.1 to 1,000 liters, and preferably 0.2 to 100 liters, per mole of compound [II-2].

[0309] The reaction temperature for this reaction may be selected from the range of temperatures usually from -30°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 150°C.

[0310] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0311] After the reaction is completed, the compound [II-3] can be isolated by concentration or other procedures.

[0312] (Step 1-3) The amount of the compound [III-1] used in this reaction may be appropriately selected usually in the range of 0.5 to 5 mol, preferably 0.5 to 2.5 mol, per 1 mol of the compound [II-3].

[0313] Examples of the base that can be used in this reaction include organic bases such as triethylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-(N,N-dimethylamino)pyridine, and 2,6-lutidine; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; and alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate. The amount of the base used can be appropriately selected from a range of 1.0 to 20 mol per mol of compound [II-3], and is preferably 1.0 to 10 mol.

[0314] This reaction can be carried out in the presence of a catalyst, if necessary, and examples of the catalyst include tetrabutylammonium bromide, tetrabutylammonium chloride, 15-crown-5, 18-crown-6, etc. The amount of the catalyst used can be appropriately selected from the range of 0.001 to 1.0 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [II-3].

[0315] Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; esters such as ethyl acetate, butyl acetate, and ethyl propionate; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; and mixtures thereof. The amount of solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per mole of Compound [II-3].

[0316] The reaction temperature for this reaction may be selected from any temperature range from -20°C to the reflux temperature of the reaction system, and is preferably in the range of 0 to 80°C.

[0317] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually from 1 minute to 48 hours.

[0318] After the reaction is complete, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated, to isolate compound [I-1]. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0319] (Step 1-4) The amount of the compound [III-1] used in this reaction may be appropriately selected in the range of 1.0 to 3.0 mol per 1 mol of the compound [II-2], and is preferably 1.0 to 1.5 mol.

[0320] Condensing agents that can be used in this reaction include, for example, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, 1H-benzo[a]pyrrolidone, 1H-benzo[b ... Examples of the condensing agent include benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, {{[(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy}-4-morpholinomethylene}dimethylammonium hexafluorophosphate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, and propylphosphonic anhydride. The amount of the condensing agent used may be appropriately selected from a range of 1.0 to 5.0 mol, and preferably 1.0 to 3.0 mol, per 1 mol of compound [II-2].

[0321] When a catalyst is used in this reaction, examples of the catalyst that can be used include 4-(N,N-dimethylamino)pyridine, etc. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 1.0 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [II-2].

[0322] When an additive is used in this reaction, examples of the additive that can be used include 1-hydroxybenzotriazole, N-hydroxysuccinimide, 1-hydroxy-7-azabenzotriazole, etc. The amount of the additive used may be appropriately selected from the range of 0.01 to 3.0 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [II-2].

[0323] When a base is used in this reaction, examples of the base that can be used include organic bases such as triethylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-(N,N-dimethylamino)pyridine, and 2,6-lutidine. The amount of the base used may be appropriately selected in the range of 0.1 to 10 mol, preferably 0.1 to 5.0 mol, per 1 mol of compound [II-2].

[0324] Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; esters such as ethyl acetate, butyl acetate, and ethyl propionate; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; and mixtures thereof. The amount of solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per mole of Compound [II-2].

[0325] The reaction temperature for this reaction may be selected from any temperature range from -20°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 80°C.

[0326] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 120 hours.

[0327] After the reaction is complete, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated, to isolate compound [I-1]. The isolated compound [I-1] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0328] <Production Method 2> Among the compounds of the present invention, the compound represented by the general formula [I-2] can also be produced according to the following method.

[0329]

[0330] (In the formula, X ３represents a leaving group such as a halogen atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, a nonafluorobutanesulfonyloxy group, a benzenesulfonyloxy group, or a p-toluenesulfonyloxy group, and R ａ , R ｂ , R １ , R ２ , R ３ , R ４ , R ７ , R ８ , R ９ and Y have the same meaning as above.

[0331] That is, the compound represented by the general formula [I-2] can be produced by reacting the compound [IV-1] with the compound [V-1] in an appropriate solvent in the presence or absence of an appropriate catalyst and an appropriate base.

[0332] The amount of compound [V-1] used in this reaction may be appropriately selected from a range of 5.0 to 1,000 mol, preferably 10 to 600 mol, per 1 mol of compound [IV-1] when the boiling point of compound [V-1] is lower than 40° C. When compound [V-1] has a boiling point of 40° C. or higher, the amount may be appropriately selected from a range of 1.0 to 20 mol, preferably 1.0 to 10 mol, per 1 mol of compound [IV-1].

[0333] The catalyst that can be used in this reaction may be a transition metal complex or a transition metal used alone or in combination with a ligand. Examples of transition metal complexes include bis(triphenylphosphine)palladium dichloride, tetrakis(triphenylphosphine)palladium, tris(dibenzylideneacetone)dipalladium, and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium-dichloromethane adduct. Examples of transition metals include metallic copper, copper acetate (I), copper acetate (II), copper oxide (I), copper oxide (II), copper chloride (I), copper bromide (I), copper iodide (I), palladium-carbon, palladium chloride, palladium bromide, palladium nitrate, and palladium acetate. Examples of ligands include trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, and 1,3-bisdiphenylphosphinopropane. The amount of the metal reagent used may be appropriately selected from the range of 0.001 to 10 mol, preferably 0.01 to 5.0 mol, per 1 mol of the compound [IV-1].

[0334] Examples of the base that can be used in this reaction include inorganic bases such as alkali metal hydroxides (lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.), alkaline earth metal hydroxides (calcium hydroxide, magnesium hydroxide, etc.), alkali metal carbonates (sodium carbonate, potassium carbonate, etc.), alkali metal bicarbonates (sodium bicarbonate, potassium bicarbonate, etc.), and organic bases such as triethylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-N,N-dimethylaminopyridine, 2,6-lutidine, etc. The amount of the base used is 0.1 to 10 mol, preferably 0.1 to 3.0 mol, per 1 mol of compound [IV-1].

[0335] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per mole of the compound [IV-1].

[0336] The reaction temperature for this reaction may be selected from the range of temperatures usually from −30° C. to the reflux temperature of the reaction system, and is preferably in the range of 0° C. to 150° C. This reaction can also be carried out under microwave irradiation.

[0337] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0338] After the reaction is complete, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated, to isolate compound [I-2]. The isolated compound [I-2] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0339] <Production Method 3> Among the compounds of the present invention, the compound represented by the general formula [I-4] can also be produced according to the following method.

[0340]

[0341] (In the formula, U１ is a hydrogen atom, a dihydroxyboryl group (-B(OH) ２ ) or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, R １１ is C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, tri(C1-C6 alkyl)silyl C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ６ ~C １２ represents an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), and X ３ , R １ , R ２ , R ３ , R ４ , R ７ , R ９ , Y, and Q have the same meanings as above.)

[0342] That is, the compound represented by the general formula [I-4] can be produced by reacting the compound [I-3] with the compound [V-2] in an appropriate solvent in the presence of an appropriate catalyst and an appropriate base.

[0343] The amount of the compound [V-2] used in this reaction may be appropriately selected usually in the range of 1.0 to 100 mol, preferably 1.0 to 5.0 mol, per 1 mol of the compound [I-3].

[0344] The catalyst that can be used in this reaction may be a transition metal complex or a combination of a transition metal and a ligand. Examples of transition metal complexes include bis(triphenylphosphine)palladium dichloride, tetrakis(triphenylphosphine)palladium, tris(dibenzylideneacetone)dipalladium, and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium-dichloromethane adduct. Examples of transition metals include metallic copper, copper acetate (I), copper acetate (II), copper oxide (I), copper oxide (II), copper chloride (I), copper bromide (I), copper iodide (I), palladium-carbon, palladium chloride, palladium bromide, palladium nitrate, and palladium acetate. Examples of ligands include ethylenediamine, N,N-dimethylethylenediamine, N,N-dimethylethylenediamine, and the like. '-dimethylethylenediamine, N,N,N',N'-tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, 1,3-bisdiphenylphosphinopropane, 1,1'-bis(diphenylphosphino)ferrocene, and the like. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 5.0 moles per mole of the compound [I-3], and is preferably 0.01 to 1.0 mole.

[0345] Examples of the base that can be used in this reaction include organic bases such as triethylamine, tributylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 2-chloropyridine, 4-N,N-dimethylaminopyridine, and 2,6-lutidine; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; inorganic bases such as tripotassium phosphate, potassium fluoride, and cesium fluoride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount of the base used is 0.1 to 10 moles, preferably 0.1 to 5.0 moles, per mole of the compound [I-3].

[0346] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per mole of the compound [I-3].

[0347] The reaction temperature for this reaction may be selected from any temperature range from -78°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 180°C.

[0348] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours.

[0349] After the reaction is complete, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated, to isolate compound [I-4]. The isolated compound [I-4] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0350] <Production Method 4> Among the compounds of the present invention, the compound represented by the general formula [I-6] can also be produced according to the following method.

[0351]

[0352] (In the formula, U ２ is a dihydroxyboryl group (-B(OH) ２ ) or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, R １２ is C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, tri(C1-C6 alkyl)silyl C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ６ ~C １２ represents an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), and X ３ , R １ , R２ , R ３ , R ４ , R ７ , R ９ , Y, and Q have the same meanings as above.)

[0353] That is, the compound represented by the general formula [I-6] can be produced by reacting the compound [I-5] with the compound [V-3] in the presence of a suitable catalyst and a suitable base in a suitable solvent.

[0354] The amount of the compound [V-3] used in this reaction may be appropriately selected usually in the range of 1.0 to 100 mol, preferably 1.0 to 5.0 mol, per 1 mol of the compound [I-5].

[0355] The catalyst, base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Production Method 3.

[0356] After the reaction is complete, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated, to isolate compound [I-6]. The isolated compound [I-6] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0357] <Production Method 5> Among the compounds of the present invention, the compound represented by general formula [I-5] can be produced using the compound represented by general formula [I-3] according to the method consisting of the reaction scheme exemplified below.

[0358]

[0359] (In the formula, X ３ , U ２ , R １ , R ２ , R ３ , R ４ , R ７ , R ９ , Y, and Q have the same meanings as above.)

[0360] That is, the compound represented by the general formula [I-5] can be produced by reacting the compound [I-3] with a boron reagent in an appropriate solvent in the presence or absence of an appropriate base and in the presence or absence of an appropriate catalyst.

[0361] The boron reagent used in this reaction is, for example, trimethyl borate, bis(pinacolato)diboron, pinacolborane, diboronic acid, etc. The amount of the boron reagent used in this reaction may be appropriately selected usually in the range of 0.5 to 10 mol, and preferably 1.0 to 5.0 mol, per 1 mol of compound [I-3].

[0362] The catalyst, base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Production Method 3.

[0363] After the reaction is complete, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated, to isolate compound [I-5]. The isolated compound [I-5] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0364] <Production Method 6> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-3] can be produced using the compound represented by general formula [III-2] according to the method consisting of the reaction scheme exemplified below.

[0365]

[0366] (In the formula, R ７ , R ８ , R ９ and Y have the same meaning as above.

[0367] That is, the compound represented by the general formula [III-3] can be produced by reacting the compound [III-2] with a suitable reducing agent in a suitable solvent in the presence or absence of a suitable acid catalyst and in the presence or absence of a suitable phase transfer catalyst.

[0368] Examples of reducing agents that can be used in this reaction include transition metals such as iron and zinc; typical metals such as tin; alkali metal salts of borohydrides such as sodium borohydride, lithium borohydride, and lithium triethylborohydride; alkali metal salts of dithionous acid such as sodium dithionite; borane complexes of organic Lewis bases such as borane-tert-butylamine complex and borane-dimethylsulfide complex; alkali metal salts of aluminum hydrides such as lithium aluminum hydride and sodium bis(2-methoxyethoxy)aluminum hydride; and organic aluminum hydride compounds such as diisobutylaluminum hydride. The amount of the reducing agent used can be appropriately selected usually within a range of 0.25 to 50 mol per mol of compound [III-2], and is preferably 0.25 to 50 mol.

[0369] Examples of the acid catalyst that can be used in this reaction include sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid, and carboxylic acids such as formic acid, acetic acid, propionic acid, and trifluoroacetic acid. The amount of the acid catalyst used can be appropriately selected from the range of 0.01 to 10 mol, preferably 0.01 to 2.0 mol, per 1 mol of compound [III-2].

[0370] Examples of the phase-transfer catalyst that can be used in this reaction include tetrabutylammonium salts such as tetrabutylammonium bromide and tetrabutylammonium chloride. The amount of the phase-transfer catalyst used may be appropriately selected from the range of 0.01 to 10 mol, preferably 0.01 to 2.0 mol, per 1 mol of compound [III-2].

[0371] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1,000 L, and preferably 0.2 to 100 L, per 1 mol of compound [III-2].

[0372] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably from 0°C to the reflux temperature of the reaction system.

[0373] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0374] After the reaction is complete, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [III-3]. The isolated compound [III-3] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0375] <Production Method 7> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-3] can be produced using the compound represented by general formula [III-4] according to the method consisting of the reaction scheme exemplified below.

[0376]

[0377] (In the formula, X ４ represents a halogen atom, and R １３ represents a hydrogen atom or a methoxy group, and R ７ , R８ , R ９ and Y have the same meaning as above.

[0378] That is, the compound represented by the general formula [III-3] can be produced by (step 7-1) reacting the compound [III-4] with a halogenating agent in a suitable solvent in the presence or absence of a suitable catalyst to obtain the compound [III-5], (step 7-2) reacting the compound [III-5] with benzophenone imine in the presence of a suitable catalyst and in the presence or absence of a suitable base in a suitable solvent to obtain the compound [III-6], and (step 7-4) reacting the compound [III-6] in a suitable solvent in the presence or absence of a suitable acid, in the presence or absence of a suitable base, and in the presence or absence of a suitable catalyst. Alternatively, (Step 7-3) compound [III-5] is reacted with a benzylamine derivative in the presence of a suitable catalyst and in the presence or absence of a suitable base in a suitable solvent to obtain compound [III-7], and (Step 7-5) compound [III-7] is reacted in the presence or absence of a suitable acid, in the presence or absence of a suitable base, under a hydrogen gas atmosphere or in the presence or absence of a suitable catalyst in a suitable solvent to produce compound [III-7].

[0379] (Step 7-1) Examples of halogenating agents that can be used in this reaction include chlorine, sulfuryl chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, iodine, N-iodosuccinimide, 1,3-diiodo-5,5-dimethylhydantoin, potassium iodate, and mixtures thereof. The amount of the halogenating agent used can be appropriately selected from a range of 0.01 to 10 mol, preferably 0.02 to 2.0 mol, per 1 mol of compound [III-4].

[0380] Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; nitriles such as acetonitrile and propionitrile; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; sulfuric acid, water, or a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, and preferably 0.2 to 100 liters, per 1 mol of compound [III-4].

[0381] The reaction temperature for this reaction may be selected from the range of temperatures usually from -70°C to the reflux temperature of the reaction system, and is preferably in the range of -20°C to 100°C.

[0382] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0383] After the reaction is complete, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-5]. The isolated compound [III-5] can be further purified, if necessary, by column chromatography, recrystallization, or the like.

[0384] (Step 7-2) The amount of benzophenone imine used in this reaction is appropriately selected usually in the range of 1.0 to 100 mol, preferably 1.0 to 5.0 mol, per 1 mol of the compound [III-5].

[0385] The catalyst that can be used in this reaction may be a transition metal complex or a combination of a transition metal and a ligand. Examples of transition metal complexes include bis(triphenylphosphine)palladium dichloride, tetrakis(triphenylphosphine)palladium, tris(dibenzylideneacetone)dipalladium, and dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II)-dichloromethane adduct. Examples of transition metals include metallic copper, copper acetate(I), copper acetate(II), copper oxide(I), copper oxide(II), copper chloride(I), copper bromide(I), copper iodide(I), palladium-carbon, palladium chloride, palladium bromide, palladium nitrate, and palladium acetate. Examples of ligands include ethylenediamine, N,N-dimethylethylenediamine, N , N'-dimethylethylenediamine, N,N,N',N'-tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocuproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bisdimethylphosphinopropane, 1,2-bisdiphenylphosphinoethane, 1,3-bisdiphenylphosphinopropane, 1,1'-bis(diphenylphosphino)ferrocene, and the like. The amount of the catalyst used may be appropriately selected from the range of 0.001 to 5.0 mol, preferably 0.01 to 1.0 mol, per 1 mol of the compound [III-5].

[0386] Examples of the base that can be used in this reaction include organic bases such as triethylamine, tributylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 2-chloropyridine, 4-N,N-dimethylaminopyridine, and 2,6-lutidine; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; inorganic bases such as tripotassium phosphate, potassium fluoride, and cesium fluoride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount of the base used is 0.1 to 10 mol, preferably 0.1 to 5.0 mol, per 1 mol of the compound [III-5].

[0387] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water; or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per mole of the compound [III-5].

[0388] The reaction temperature for this reaction may be selected from any temperature range from -78°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 180°C.

[0389] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours.

[0390] After the reaction is complete, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-6]. The isolated compound [III-6] can be further purified, if necessary, by column chromatography, recrystallization, or the like.

[0391] (Step 7-3) The benzylamine derivative used in this reaction may be benzylamine or 4-methoxybenzylamine, and may be appropriately selected usually in the range of 1 to 100 mol, preferably 1.0 to 5.0 mol, per 1 mol of the compound [III-5].

[0392] The catalyst, base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Step 7-2.

[0393] After the reaction is complete, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated to isolate compound [III-7]. The isolated compound [III-7] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0394] (Step 7-4) Compound [III-3] can be produced, for example, according to the method described in GREEN'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. M. Wuts), by reacting compound [III-6] in a suitable solvent in the presence or absence of a suitable acid, in the presence or absence of a suitable base, under a hydrogen gas atmosphere or in the presence or absence of a suitable catalyst.

[0395] After the reaction is complete, the compound [III-3] can be isolated by filtering off insoluble matter and concentrating the filtrate, or by pouring the reaction mixture into water, extracting with an organic solvent, and then concentrating the extract. The isolated compound [III-3] can be further purified, if necessary, by column chromatography, recrystallization, or the like.

[0396] (Step 7-5) The compound [III-3] can be produced from the compound [III-7] by the same production method as in Step 7-4.

[0397] <Production Method 8> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-10] can be produced using the compound represented by general formula [III-8] according to the method consisting of the reaction scheme exemplified below.

[0398]

[0399] (In the formula, Y ２ is -C(O)-, -S(O)-, or -S(O) ２ - indicates R １４ is C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyl group, C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylamino group, C １ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), or C １ ~C １２ represents an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), and X ３ , X ４ , R ７ , R ９ , R ｉ and Y have the same meaning as above.

[0400] That is, the compound represented by the general formula [III-10] can be produced by (Step 8-1) reacting compound [III-8] with compound [V-4] in an appropriate solvent in the presence or absence of a suitable catalyst and in the presence or absence of a suitable base to obtain compound [III-9], and then (Step 8-2) reacting compound [III-9] with compound [V-5] in an appropriate solvent in the presence or absence of a suitable base and in the presence or absence of a suitable catalyst.

[0401] (Step 8-1) The amount of the compound [V-4] used in this reaction is appropriately selected usually in the range of 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, per 1 mol of the compound [III-8].

[0402] Examples of the base that can be used in this reaction include organic bases such as triethylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-(N,N-dimethylamino)pyridine, and 2,6-lutidine; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; and alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate. The amount of the base used can be appropriately selected in a range of 1.0 to 20 mol per 1 mol of compound [III-8], and is preferably 1.0 to 10 mol.

[0403] This reaction can be carried out in the presence of a catalyst, if necessary, and examples of the catalyst include tetrabutylammonium bromide, tetrabutylammonium chloride, 15-crown-5, 18-crown-6, etc. The amount of the catalyst used can be appropriately selected from the range of 0.001 to 1 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [III-8].

[0404] Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; esters such as ethyl acetate, butyl acetate, and ethyl propionate; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; and mixtures thereof. The amount of solvent used is 0.1 to 1,000 liters, preferably 0.2 to 100 liters, per 1 mol of compound [III-8].

[0405] The reaction temperature for this reaction may be selected from any temperature range from -20°C to the reflux temperature of the reaction system, and is preferably in the range of 0 to 80°C.

[0406] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually from 1 minute to 48 hours.

[0407] After the reaction is complete, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or the precipitate is extracted with an organic solvent and then concentrated to isolate compound [III-9]. The isolated compound [III-9] can be further purified by column chromatography, etc., if necessary.

[0408] (Step 8-2) The amount of the compound [V-5] used in this reaction may be appropriately selected usually in the range of 1.0 to 20 mol, preferably 1.0 to 3.0 mol, per 1 mol of the compound [III-9].

[0409] Examples of bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine, tributylamine, N-ethyldiisopropylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base used can be appropriately selected from a range of 0.5 to 10 mol per 1 mol of compound [III-9], and is preferably 1.0 to 5.0 mol.

[0410] Examples of the catalyst that can be used in this reaction include alkali metal iodides such as sodium iodide and potassium iodide. The amount of the catalyst used can be appropriately selected from the range of 0.01 to 0.5 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [III-9].

[0411] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water, or a mixed solvent thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-9].

[0412] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 100°C.

[0413] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0414] After completion of the reaction, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [III-10]. The isolated compound [III-10] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0415] <Production Method 9> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-14] can be produced using the compound represented by general formula [III-11] according to the method consisting of the reaction scheme exemplified below.

[0416]

[0417] (wherein K represents a 3- to 6-membered carbocyclic ring, R １５ is a cyano group, or C １ ~C ６ represents an alkoxycarbonyl group, and R ７ , R ９ and Y have the same meaning as above.

[0418] That is, the compound represented by the general formula [III-14] can be produced by (step 9-1) reacting the compound [III-11] with the compound [V-6] in the presence or absence of a suitable base and in the presence or absence of a suitable catalyst in a suitable solvent to obtain the compound [III-12], (step 9-2) nitrating the compound represented by the general formula [III-12] to obtain the compound [III-13], and (step 9-3) hydrolyzing the compound [III-13] in the presence of a suitable acid or base in a suitable solvent.

[0419] (Step 9-1) Examples of the compound [V-6] used in this reaction include 1,2-dibromoethane, 1,2-diiodoethane, 1,3-dibromopropane, 1,3-diiodopropane, 1,4-dibromobutane, 1,5-dibromopentane, ethylene carbonate, etc. The amount of the compound [V-6] used may be appropriately selected from a range of 1.0 to a mole equivalent to the amount of the solvent, per mole of the compound [III-11], and is preferably 1.0 to 20 moles.

[0420] Examples of bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine, tributylamine, N-ethyldiisopropylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base used can be appropriately selected from a range of 0.5 to 20 mol per 1 mol of compound [III-11], and is preferably 1.0 to 10 mol.

[0421] Examples of the catalyst that can be used in this reaction include alkali metal iodides such as sodium iodide and potassium iodide. The amount of the catalyst used can be appropriately selected from the range of 0.01 to 0.5 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [III-11].

[0422] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water, or a mixed solvent thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-11].

[0423] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 100°C.

[0424] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0425] After completion of the reaction, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [III-12]. The isolated compound [III-12] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0426] (Step 9-2) The compound represented by the general formula [III-13] can be produced by nitrating the compound represented by the general formula [III-12] in accordance with the method described in "Nitro and Nitroso Compounds" in Vol. 20 of "Experimental Chemistry Lectures," 4th Edition (Maruzen).

[0427] Compound [III-13] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0428] (Step 9-3) The acid, base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Step 1-1.

[0429] After completion of the reaction, the reaction mixture is poured into water for neutralization, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-14]. The isolated compound [III-14] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0430] <Production Method 10> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-18] can be produced using the compound represented by general formula [III-15] according to the method consisting of the reaction scheme exemplified below.

[0431]

[0432] (In the formula, Z ２ represents a hydrogen atom, a halogen atom, or a nitro group, and R １６ is C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α), a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from Substituent Group α), and R １７ is a hydrogen atom or C １ ~C ６ represents an alkyl group, and X２ , X ４ , R ７ , R ９ and Y have the same meaning as above.

[0433] That is, the compound represented by the general formula [III-18] can be produced by (Step 10-1) converting the compound [III-15] into an active derivative such as an acid halide or a mixed acid anhydride, compound [III-16], in an appropriate solvent in the presence or absence of a suitable catalyst, followed by (Step 10-2) reacting the compound with a methoxyamine in an appropriate solvent in the presence or absence of a suitable base and in the presence or absence of a suitable catalyst to produce compound [III-17], and then (Step 10-4) reacting the compound [III-17] with a Grignard reagent or a lithium reagent represented by compound [V-7] in an appropriate solvent in the presence or absence of a suitable additive. Alternatively, (Step 10-3) compound [III-15] can be reacted with a methoxyamine in the presence or absence of a suitable condensing agent and a suitable additive, in the presence or absence of a suitable catalyst, and in the presence or absence of a suitable base in an appropriate solvent to obtain compound [III-17], followed by Step 10-4.

[0434] (Step 10-1) The reagents, acid, base, solvent, reaction temperature and reaction time that can be used in this reaction to convert compound [III-15] to compound [III-16] are the same as those in Step 1-2.

[0435] After completion of the reaction, compound [III-16] can be isolated by carrying out an operation such as concentration.

[0436] (Step 10-2) Examples of methoxyamines that can be used in this reaction include methoxyamine, methoxyamine hydrochloride, methoxyamine sulfate, N,O-dimethylhydroxylamine hydrochloride, etc. The amount of the methoxyamine used can be appropriately selected usually in the range of 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, per 1 mol of compound [III-16].

[0437] The base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Steps 1-3.

[0438] After completion of the reaction, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the compound [III-17] can be isolated by extraction with an organic solvent followed by concentration, or the like.

[0439] (Step 10-3) Examples of methoxyamines that can be used in this reaction include methoxyamine, methoxyamine hydrochloride, methoxyamine sulfate, etc. The amount of the methoxyamine used can be appropriately selected in the range of 1.0 to 3.0 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [III-15].

[0440] The condensing agent, additive, base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Steps 1-4.

[0441] After completion of the reaction, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the precipitate is extracted with an organic solvent and then concentrated to isolate compound [III-17]. The isolated compound [III-17] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0442] (Step 10-4) The amount of the compound [V-7] used in this reaction may be appropriately selected usually in the range of 1.0 to 10 mol, preferably 1.0 to 4.0 mol, per 1 mol of the compound [III-17].

[0443] Examples of additives that can be used in this reaction include N,N,N',N'-tetramethylethylenediamine, hexamethylphosphoramide, N,N'-dimethylpropyleneurea, etc. The amount of the additive used is 1.0 to 10 mol, and preferably 1.0 to 3.0 mol, per 1 mol of compound [III-17].

[0444] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, diisopropyl ether, tert-butyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; and mixed solvents thereof. The amount of the solvent used is 0.1 to 1,000 L, and preferably 0.2 to 100 L, per 1 mol of compound [III-17].

[0445] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably in the range of -78°C to 70°C.

[0446] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0447] Compound [III-18] can be isolated by concentrating the mixture, etc. The isolated compound [III-18] can be further purified by column chromatography, recrystallization, etc., if necessary.

[0448] <Production Method 11> Among the intermediates of the compound of the present invention, the compounds represented by the general formula [III-20] and the general formula [III-21] can be produced using the compound represented by the general formula [III-18] according to the method consisting of the reaction scheme exemplified below.

[0449]

[0450] (In the formula, R １８ is C １ ~C ６ Alkyl group, C ３ ~C ８a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, or C ３ ~C ８ represents a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β); Z ２ , X ３ , X ４ , R ７ , R ９ , R １６ and Y have the same meaning as above.

[0451] That is, the compound represented by the general formula [III-20] can be produced by (Step 11-1) reacting the compound represented by the general formula [III-18] with a suitable reducing agent in a suitable solvent to obtain the compound [III-19], and then (Step 11-2) reacting the compound [III-19] with the compound [V-8] in the presence or absence of a suitable catalyst and in the presence or absence of a suitable base in a suitable solvent. The compound represented by the general formula [III-21] can be produced by (Step 11-3) reacting the compound [III-19] with a suitable halogenating agent in a suitable solvent in the presence or absence of a suitable base and in the presence or absence of a suitable additive.

[0452] (Step 11-1) Examples of reducing agents that can be used in this reaction include alkali metal salts of boron hydrides, such as sodium borohydride, lithium borohydride, and lithium triethylborohydride; borane complexes of organic Lewis bases, such as borane-tert-butylamine complex and borane-dimethylsulfide complex; alkali metal salts of aluminum hydrides, such as lithium aluminum hydride and sodium bis(2-methoxyethoxy)aluminum hydride; and organic aluminum hydride compounds, such as diisobutylaluminum hydride. The amount of the reducing agent used can be appropriately selected from a range of 0.25 to 5.0 mol per mol of compound [III-18], and is preferably 0.25 to 2.0 mol.

[0453] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; alcohols such as methanol, ethanol, and 2-propanol; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1,000 L, and preferably 0.2 to 100 L, per 1 mol of compound [III-18].

[0454] The reaction temperature for this reaction may be selected from any temperature range from -78°C to the reflux temperature of the reaction system, and is preferably in the range of -10°C to 60°C.

[0455] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0456] The reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [III-19]. The isolated compound [III-19] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0457] (Step 11-2) The amount of the compound [V-8] used in this reaction may be appropriately selected in a range of 1.0 to 15 mol, preferably 1.0 to 6.0 mol, per 1 mol of the compound [III-19].

[0458] Examples of bases that can be used in this reaction include inorganic bases such as alkali metal hydroxides (e.g., sodium hydroxide, potassium hydroxide, etc.); alkaline earth metal hydroxides (e.g., calcium hydroxide, magnesium hydroxide, etc.); alkali metal carbonates (e.g., sodium carbonate, potassium carbonate, etc.); alkali metal bicarbonates (e.g., sodium hydrogencarbonate, potassium hydrogencarbonate, etc.); metal hydrides (e.g., sodium hydride, potassium hydride, etc.); metal salts of alcohols (e.g., sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc.); and organic bases (e.g., triethylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-(N,N-dimethylamino)pyridine, 2,6-lutidine, etc.). The amount of the base used can be appropriately selected from a range of 1.0 to 5.0 mol per 1 mol of compound [III-19], and is preferably 1.0 to 1.5 mol.

[0459] Examples of the catalyst that can be used in this reaction include tetrabutylammonium bromide, tetrabutylammonium iodide, etc. The amount of the catalyst used may be appropriately selected from the range of 0.01 to 1.0 mol, preferably 0.05 to 0.5 mol, per 1 mol of compound [III-19].

[0460] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, and 2-propanol; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine and picoline; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-19].

[0461] The reaction temperature for this reaction may be selected from the range of temperatures usually from -30°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 150°C.

[0462] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours.

[0463] The reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated, to isolate compound [III-20]. The isolated compound [III-20] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0464] (Step 11-3) Examples of the halogenating agent that can be used in this reaction include hydrohalic acids such as hydrochloric acid and hydrobromic acid; alkali metal halides such as lithium chloride and sodium bromide; thionyl chloride, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphoryl chloride, hexachloroacetone, carbon tetrachloride, carbon tetrabromide, etc. The amount of the halogenating agent used in this reaction can be appropriately selected in a range of 0.5 to 30 mol, preferably 0.5 to 4.0 mol, per 1 mol of compound [III-19].

[0465] Examples of the catalyst that can be used in this reaction include N,N-dimethylformamide, zinc chloride, etc. The amount of the catalyst used may be appropriately selected from the range of 0.01 to 10 mol, preferably 0.01 to 1.0 mol, per 1 mol of compound [III-19].

[0466] When an additive is used in this reaction, examples of the additive that can be used include triphenylphosphine, tributylphosphine, sulfuric acid, etc. The amount of the additive used may be appropriately selected in the range of 0.01 to 3.0 mol, preferably 1.0 to 1.5 mol, per 1 mol of compound [III-19].

[0467] Examples of the base that can be used in this reaction include triethylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-(N,N-dimethylamino)pyridine, 2,6-lutidine, etc. The amount of the base used can be appropriately selected in a range of 1.0 to 20 mol, preferably 1.0 to 5.0 mol, per 1 mol of compound [III-19].

[0468] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; and mixed solvents thereof. The amount of the solvent used is 0.1 to 1,000 L, and preferably 0.2 to 100 L, per 1 mol of compound [III-19].

[0469] The reaction temperature for this reaction may be selected from the range of temperatures usually from -40°C to the reflux temperature of the reaction system, and is preferably in the range of -20°C to 120°C.

[0470] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0471] The reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [III-21]. The isolated compound [III-21] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0472] <Production Method 12> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-22] can be produced using the compound represented by general formula [III-18] according to the method consisting of the reaction scheme exemplified below.

[0473]

[0474] (In the formula, R １９ is C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C１ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl-C ２ ~C ６ an alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from Substituent Group α) or a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from Substituent Group α); Z ２ , X ４ , R ７ , R ９ , R １６ and Y have the same meaning as above.

[0475] That is, the compound represented by the general formula [III-22] can be produced by reacting the compound [III-18] with the compound [V-9] in an appropriate solvent in the presence or absence of an appropriate additive.

[0476] The amount of the compound [V-9] used in this reaction may be appropriately selected in the range of 1.0 to 10 mol per 1 mol of the compound [III-18], and is preferably 1.0 to 5.0 mol.

[0477] Examples of additives that can be used in this reaction include N,N,N',N'-tetramethylethylenediamine, hexamethylphosphoramide, N,N'-dimethylpropyleneurea, etc. The amount of the additive used is 1.0 to 10 mol, and preferably 1.0 to 3.0 mol, per 1 mol of compound [III-18].

[0478] Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; and mixed solvents thereof. The amount of the solvent to be used is 0.1 to 1,000 L, and preferably 0.2 to 100 L, per 1 mol of compound [III-18].

[0479] The reaction temperature for this reaction may generally be selected from the range of -80°C to the reflux temperature of the reaction system, and is preferably in the range of -80°C to 100°C.

[0480] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 36 hours.

[0481] After completion of the reaction, the reaction mixture is poured into water or the like, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-22]. The isolated compound [III-22] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0482] <Production Method 13> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-26] can be produced using the compound represented by general formula [III-23] according to the method consisting of the reaction scheme exemplified below.

[0483]

[0484] (In the formula, R ２０ is C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from Substituent Group α) or a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from Substituent Group α); Z ２ , X ４ , R ７ , R ９and Y have the same meaning as above.

[0485] That is, the compound represented by the general formula [III-26] can be produced by (step 13-1) reacting the compound [III-23] with the compound [V-10] in an appropriate solvent to give the compound [III-24], (step 13-2) converting the compound [III-24] into the compound [III-25] by a dehydration reaction, and (step 13-3) subjecting the compound [III-25] to a Simmons-Smith reaction.

[0486] (Step 13-1) The compound [III-24] can be produced in the same manner as in Production Method 12.

[0487] (Step 13-2) The compound represented by the general formula [III-25] can be produced by dehydrating the compound represented by the general formula [III-24] in accordance with the method described in "Experimental Chemistry Lectures," 4th edition (Maruzen), Vol. 19, "Section on Hydrocarbons."

[0488] Compound [III-25] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0489] (Step 13-3) The compound represented by the general formula [III-26] can be produced by the Simmons-Smith reaction of the compound represented by the general formula [III-25] in accordance with the method described in "Synthesis using Group 12 organometallic compounds" in Vol. 25 of "Experimental Chemistry Lectures," 4th edition (Maruzen).

[0490] Compound [III-26] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0491] <Production Method 14> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-27] can be produced using the compound represented by general formula [III-21] according to the method consisting of the reaction scheme exemplified below.

[0492]

[0493] (In the formula, R ２１ is C １ ~C ６ Alkyl group, C ３~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ６ ~C １２ represents an aryl group (the aryl group may be substituted with one or more substituents selected from Substituent Group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from Substituent Group α), and A ３ represents an oxygen atom, a sulfur atom, or —NH—; Z ２ , X ４ , R ７ , R ９ , R １６ and Y have the same meaning as above.

[0494] That is, the compound represented by the general formula [III-27] can be produced by reacting the compound [III-21] with the compound [V-11] in the presence of a suitable base and in the presence or absence of a suitable catalyst in a suitable solvent.

[0495] The amount of the compound [V-11] used in this reaction may be appropriately selected ordinarily in the range of 1.0 to 5.0 mol, preferably 1.0 to 4.0 mol, per 1 mol of the compound [III-21].

[0496] Examples of bases that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine, tributylamine, N-ethyldiisopropylamine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base used can be appropriately selected from a range of 0.5 to 20 mol per 1 mol of compound [III-21], and is preferably 1.0 to 5.0 mol.

[0497] Examples of the catalyst that can be used in this reaction include alkali metal iodides such as sodium iodide and potassium iodide. The amount of the catalyst used can be appropriately selected from the range of 0.01 to 0.5 mol, preferably 0.01 to 0.1 mol, per 1 mol of compound [III-21].

[0498] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 4-methyltetrahydropyran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water, or a mixed solvent thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-21].

[0499] The reaction temperature for this reaction may be selected from the range of temperatures usually from -78°C to the reflux temperature of the reaction system, and is preferably in the range of -20°C to 100°C.

[0500] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0501] After completion of the reaction, the reaction mixture is poured into water, extracted with an organic solvent, and then concentrated to isolate compound [III-27]. The isolated compound [III-27] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0502] <Production Method 15> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-30] can be produced using the compound represented by general formula [III-21] according to the method consisting of the reaction scheme exemplified below.

[0503]

[0504] (In the formula, R ２２ is C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), or C １ ~C ６ Alkoxy C １ ~C ６ represents an alkyl group; Z ２ , X ３ , X ４ , R ７ , R ９ , R １６ and Y have the same meaning as above.

[0505] That is, the compound represented by the general formula [III-30] can be produced by (step 15-1) reacting compound [III-21] with a thioacetate salt in an appropriate solvent to obtain compound [III-28], (step 15-2) reacting compound [III-28] in the presence of an appropriate acid or base, or in the presence of an appropriate reducing agent in an appropriate solvent to obtain compound [III-29], and (step 15-3) reacting compound [III-29] with compound [V-12] in the presence or absence of an appropriate base and in the presence or absence of an appropriate radical initiator in an appropriate solvent.

[0506] (Step 15-1) Examples of the thioacetate that can be used in this reaction include sodium thioacetate, potassium thioacetate, etc. The amount of the thioacetate used can be appropriately selected in the range of 1.0 to 5.0 mol, preferably 1.0 to 3.5 mol, per 1 mol of compound [III-21].

[0507] Examples of solvents that can be used in this reaction include alcohols such as methanol, ethanol, and 2-propanol; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; esters such as ethyl acetate, butyl acetate, and ethyl propionate; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-21].

[0508] The reaction temperature for this reaction may be selected from the range of temperatures usually from -30°C to the reflux temperature of the reaction system, and is preferably in the range of -10°C to 40°C.

[0509] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0510] After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-28]. The isolated compound [III-28] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0511] (Step 15-2) Examples of the acid that can be used in this reaction include mineral acids such as hydrochloric acid, hydrobromic acid, and sulfuric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; and sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid. The amount of the acid to be used may be appropriately selected within a range of 1.0 to the mole equivalent to the amount of the solvent, per mole of compound [III-28], and is preferably 1.0 to 100 moles.

[0512] Examples of the base that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, etc.; alkaline earth metal hydroxides such as calcium hydroxide, magnesium hydroxide, etc.; alkali metal carbonates such as sodium carbonate, potassium carbonate, etc.; inorganic bases such as alkali metal bicarbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, etc.; metal hydrides such as sodium hydride, potassium hydride, etc.; and metal salts of alcohols such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, etc. The amount of the base used can be appropriately selected in a range of 0.1 to 50 mol per 1 mol of compound [III-28], and is preferably 0.5 to 20 mol.

[0513] Examples of the reducing agent that can be used in this reaction include sodium borohydride, lithium aluminum hydride, diisobutylaluminum hydride, sodium bis(2-methoxyethoxy)aluminum hydride, etc. The amount of the reducing agent used can be appropriately selected in a range of 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, per 1 mol of compound [III-28].

[0514] Examples of solvents that can be used in this reaction include alcohols such as methanol, ethanol, and 2-propanol; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; esters such as ethyl acetate, butyl acetate, and ethyl propionate; nitriles such as acetonitrile and propionitrile; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-28].

[0515] The reaction temperature for this reaction may be selected from the range of temperatures usually from -30°C to the reflux temperature of the reaction system, and is preferably in the range of -10°C to 40°C.

[0516] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0517] After completion of the reaction, the reaction mixture is poured into water for neutralization, and the precipitated solid is then filtered off, or extracted with an organic solvent and concentrated to isolate compound [III-29]. The isolated compound [III-29] can be further purified, if necessary, by column chromatography, recrystallization, or the like.

[0518] (Step 15-3) The amount of the compound [V-12] used in this reaction may be appropriately selected in the range of 1.0 to 100 mol, preferably 1.0 to 3.5 mol, per 1 mol of the compound [III-29].

[0519] Examples of the base that can be used in this reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; metal hydrides such as sodium hydride and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine, N,N-dimethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base used can be appropriately selected in a range of 1.0 to 5.0 mol per 1 mol of compound [III-29], and is preferably 1.0 to 3.0 mol.

[0520] Examples of the radical initiator that can be used in this reaction include sulfurous acid, sulfite salts, and sulfite adducts such as Rongalit (trade name, sodium formaldehyde sulfoxylate). The amount of the radical initiator used can be appropriately selected from a range of 0.01 to 5.0 mol, preferably 0.01 to 1.5 mol, per 1 mol of compound [III-29].

[0521] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, and 2-propanol; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine and picoline; water, or a mixed solvent thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-29].

[0522] The reaction temperature for this reaction may be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 150°C.

[0523] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 24 hours.

[0524] After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-30]. The isolated compound [III-30] can be further purified by column chromatography, recrystallization, or the like, as necessary.

[0525] <Production Method 16> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-33] can be produced using the compound represented by general formula [III-14] according to the method consisting of the reaction scheme exemplified below.

[0526]

[0527] (In the formula, K, ４ , R ７ , R ９ and Y have the same meaning as above.

[0528] That is, the compound of general formula [III-33] can be produced by (step 16-1) reacting compound [III-14] in the presence of a suitable reducing agent in a suitable solvent to obtain compound [III-31], then (step 16-2) reacting compound [III-31] in the presence of a suitable halogenating agent in a suitable solvent to obtain compound [III-32], and (step 16-3) reacting compound [III-32] with a cyanating agent in the presence or absence of a suitable base in a suitable solvent.

[0529] (Step 16-1) The compound represented by the general formula [III-31] can be produced by reducing the compound represented by the general formula [III-14] in accordance with the method described in "General Reduction" in Vol. 26 of "Experimental Chemistry Lectures," 4th Edition (Maruzen).

[0530] Compound [III-31] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0531] (Step 16-2) The halogenating agent and the amount of halogenating agent used in this reaction, the catalyst, additive, base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Step 11-3.

[0532] The reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [III-32]. The isolated compound [III-32] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0533] (Step 16-3) Examples of the cyanating agent used in this reaction include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, and mixtures thereof. The amount of the cyanide compound used is appropriately selected usually in the range of 1.0 to 100 mol, and preferably 1.0 to 5.0 mol, per 1 mol of compound [III-32].

[0534] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, and 2-propanol; nitriles such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine and picoline; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-32].

[0535] The reaction temperature for this reaction may be selected from the range of temperatures usually from -30°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 150°C.

[0536] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0537] After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [III-33]. The isolated compound [III-33] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0538] <Production Method 17> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-36] can be produced using the compound represented by general formula [III-15] according to the method consisting of the reaction scheme exemplified below.

[0539]

[0540] (In the formula, Z ２ , X ３ , X ４ , R ７ , R ９ , R １０ , R １８ and Y have the same meaning as above.

[0541] That is, the compound represented by the general formula [III-36] can be produced by (step 17-1) esterifying compound [III-15] to give compound [III-34], (step 17-2) reacting compound [III-34] with tetraalkyl orthotitanate and ethyl magnesium halide in an appropriate solvent to give compound [III-35], and (step 17-3) reacting compound [III-35] with compound [V-8] in the presence or absence of an appropriate base in an appropriate solvent.

[0542] (Step 17-1) The compound represented by the general formula [III-34] can be produced by esterifying the compound represented by the general formula [III-15] in accordance with the method described in "Experimental Chemistry Lectures," 4th edition (Maruzen), Vol. 22, "Carboxylic Acids and Derivatives."

[0543] Compound [III-34] can be further purified by column chromatography, recrystallization, or the like, if necessary.

[0544] (Step 17-2) Examples of the tetraalkyl orthotitanate used in this reaction include tetraethyl orthotitanate, tetraisopropyl orthotitanate, tetrabutyl orthotitanate, tetraisobutyl orthotitanate, tetrakis(2-ethylhexyl) orthotitanate, etc. The amount of the tetraalkyl orthotitanate used may be appropriately selected usually in the range of 1.0 to 10 mol, and preferably 1.0 to 3.0 mol, per 1 mol of compound [III-34].

[0545] Examples of the ethylmagnesium halide used in this reaction include ethylmagnesium chloride, ethylmagnesium bromide, and ethylmagnesium iodide. The amount of the ethylmagnesium halide used is appropriately selected usually in a range of 1.0 to 10 mol, and preferably 1.0 to 5.0 mol, per 1 mol of compound [III-34].

[0546] Examples of the solvent that can be used in this reaction include ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, etc.; and mixed solvents thereof. The amount of the solvent to be used is 0.1 to 1000 L, and preferably 0.2 to 100 L, per 1 mol of compound [III-34].

[0547] The reaction temperature for this reaction may be selected from the range of temperatures usually from -30°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 100°C.

[0548] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0549] After completion of the reaction, the reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [III-35]. The isolated compound [III-35] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0550] (Step 17-3) The amount of the compound [V-8] used in this reaction is appropriately selected in the range of 1.0 to 100 mol, preferably 1.0 to 3.5 mol, per 1 mol of the compound [III-35].

[0551] Examples of the base that can be used in this reaction include organic bases such as triethylamine, tributylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 2-chloropyridine, 4-N,N-dimethylaminopyridine, and 2,6-lutidine; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate; inorganic bases such as tripotassium phosphate, potassium fluoride, and cesium fluoride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount of the base to be used is 0.1 to 10 mol, preferably 0.1 to 5.0 mol, per 1 mol of the compound [III-35].

[0552] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, methyl tert-butyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, and monoglyme; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, and methyl cellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, picoline, and lutidine; tertiary amines such as triethylamine and tributylamine; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1000 liters, preferably 0.2 to 100 liters, per 1 mol of the compound [III-35].

[0553] The reaction temperature for this reaction may be selected from any temperature range from -30°C to the reflux temperature of the reaction system, and is preferably in the range of -10°C to 150°C.

[0554] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 48 hours.

[0555] After completion of the reaction, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or extracted with an organic solvent and then concentrated to isolate compound [III-36]. The isolated compound [III-36] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0556] <Production Method 18> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-38] can be produced using the compound represented by general formula [III-14] according to the method consisting of the reaction scheme exemplified below.

[0557]

[0558] (In the formula, K, R ７ , R ９ , R １０ and Y have the same meaning as above.

[0559] That is, the compound of general formula [III-38] can be produced by (step 18-1) reacting compound [III-14] with diphenylphosphoryl azide (DPPA) in an appropriate solvent in the presence of an appropriate base to give compound [III-37], and then (step 18-2) reacting compound [III-37] with compound [V-13].

[0560] (Step 18-1) The amount of DPPA used in this reaction may be appropriately selected in the range of 1.0 to 5.0 mol per 1 mol of the compound [III-14], and is preferably 1.0 to 2.5 mol.

[0561] Examples of the base that can be used in this reaction include organic bases such as triethylamine, N,N-dimethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and magnesium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; and alkali metal bicarbonates such as sodium hydrogencarbonate and potassium hydrogencarbonate. The amount of the base used can be appropriately selected in a range of 1.0 to 5.0 mol per 1 mol of compound [III-14], and is preferably 1.0 to 2.5 mol.

[0562] Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; alcohols such as methanol, ethanol, and 2-propanol; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolidinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1,000 L, preferably 0.2 to 100 L, per 1 mol of compound [III-14].

[0563] (Step 18-2) Examples of the compound [V-13] that can be used in this reaction include alcohols such as methanol, ethanol, 2-propanol, tert-butyl alcohol, etc. The amount of the compound [V-13] used may be appropriately selected from a range of 1.0 to the mole equivalent to the amount of the solvent, per mole of the compound [III-37], and is preferably 1.0 to 100 moles.

[0564] The reaction temperature for this reaction may be selected from any temperature range from -20°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 120°C.

[0565] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, and reaction amount, but is usually from 1 minute to 48 hours.

[0566] After completion of the reaction, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the precipitate is extracted with an organic solvent and then concentrated to isolate compound [III-38]. The isolated compound [III-38] can be further purified by column chromatography, recrystallization, or the like, as necessary.

[0567] <Production Method 19> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-40] can be produced using the compound represented by general formula [III-39] according to the method consisting of the reaction scheme exemplified below.

[0568]

[0569] (In the formula, R ｉ , R ｋ , Z ２ , X ４ , R ７ , R ９ and Y have the same meaning as above.

[0570] That is, the compound represented by the general formula [III-40] can be produced by reacting the compound [III-39] with the compound [V-14] in the presence or absence of a suitable catalyst and in the presence or absence of a suitable base in a suitable solvent.

[0571] The amount of the compound [V-14] used in this reaction may be appropriately selected ordinarily in the range of 1.0 to 100 mol, preferably 1.0 to 10 mol, per 1 mol of the compound [III-39].

[0572] The catalyst, base, solvent, reaction temperature and reaction time that can be used in this reaction are the same as those in Step 7-2.

[0573] After completion of the reaction, the reaction mixture is poured into water and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated to isolate compound [III-40]. The isolated compound [III-40] can be further purified by column chromatography, recrystallization, or the like, as necessary.

[0574] <Production Method 20> Among the intermediates of the compound of the present invention, the compound represented by general formula [III-3] can be produced using the compound represented by general formula [III-41] according to the method consisting of the reaction scheme exemplified below.

[0575]

[0576] (In the formula, R ７ , R ８ , R９ , R １０ and Y have the same meaning as above.

[0577] That is, the compound represented by the general formula [III-3] can be produced by (Step 20-1) hydrolyzing compound [III-41] in the presence of a suitable base or a suitable acid in an appropriate solvent to give compound [III-42], (Step 20-2) subjecting compound [III-42] to a Curtius rearrangement reaction, followed by treatment with compound [V-13] to give compound [III-43], and (Step 20-3) reacting compound [III-43] in the presence or absence of a suitable acid, in the presence or absence of a suitable base, and in the presence or absence of a suitable catalyst in an appropriate solvent.

[0578] (Step 20-1) Examples of the base that can be used in this reaction include inorganic bases such as alkali metal hydroxides (e.g., sodium hydroxide, potassium hydroxide, lithium hydroxide, barium hydroxide, etc.); alkali metal carbonates (e.g., sodium carbonate, potassium carbonate, etc.); alkali metal bicarbonates (e.g., sodium hydrogencarbonate, potassium hydrogencarbonate, etc.). The amount of the base used can be appropriately selected in the range of 0.1 to 50 mol, preferably 0.5 to 20 mol, per 1 mol of compound [III-41].

[0579] Examples of the acid that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, and sulfuric acid; and carboxylic acids such as acetic acid and trifluoroacetic acid. The amount of the acid to be used is appropriately selected in a range of 1.0 to 1,000 mol, preferably 1.0 to 100 mol, per 1 mol of compound [III-41].

[0580] Examples of solvents that can be used in this reaction include ethers such as diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and 1,4-dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; aprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, and sulfolane; alcohols such as methanol, ethanol, and 2-propanol; nitriles such as acetonitrile and propionitrile; ketones such as acetone and methyl ethyl ketone; water, or a mixture thereof. The amount of the solvent used is 0.1 to 500 L, and preferably 0.3 to 30 L, per 1 mol of compound [III-41].

[0581] The reaction temperature for this reaction may be selected from the range of temperatures usually from -30°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 150°C.

[0582] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is usually 10 minutes to 72 hours.

[0583] After completion of the reaction, the reaction mixture is poured into water for neutralization, and the precipitated solid is then filtered off, or extracted with an organic solvent and concentrated to isolate compound [III-42]. The isolated compound [III-42] can be further purified by column chromatography, recrystallization, or the like, as necessary.

[0584] (Step 20-2) The compound [III-43] can be produced from the compound [III-42] by the same method as in Production Method 18.

[0585] The reaction mixture is poured into water, and the precipitated solid is collected by filtration or extracted with an organic solvent and then concentrated to isolate compound [III-43]. The isolated compound [III-43] can be further purified by column chromatography, recrystallization, etc., as necessary.

[0586] (Step 20-3) Compound [III-3] can be produced, for example, according to the method described in GREEN'S PROTECTIVE GROUPS in Organic Synthesis; 5th Edition (John Wiley and Sons, 2014, Peter G. M. Wuts), by reacting compound [III-43] in a suitable solvent in the presence or absence of a suitable acid, in the presence or absence of a suitable base, and in the presence or absence of a suitable catalyst.

[0587] <Production Method 21> Among the intermediates of the compound of the present invention, the compounds represented by the general formula [II-5] and the general formula [II-6] can be produced using the compound represented by the general formula [II-4] according to the method consisting of the reaction scheme exemplified below.

[0588]

[0589] (In the formula, X ４ , R １ , R ２ , and R １０ has the same meaning as above.)

[0590] That is, the compounds represented by the general formula [II-5] and the general formula [II-6] can be produced by reacting the compound [II-4] with a halogenating agent in an appropriate solvent in the presence or absence of an appropriate radical initiator, in the presence of an appropriate base or an appropriate acid, and in the presence or absence of light irradiation.

[0591] The amount of the halogenating agent used in this reaction may be appropriately selected within a range of 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, per 1 mol of the compound [II-4].

[0592] Examples of halogenating agents that can be used in this reaction include chlorine, sulfuryl chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, iodine, N-iodosuccinimide, 1,3-diiodo-5,5-dimethylhydantoin, potassium iodate, and mixtures thereof. The amount of the halogenating agent used may be appropriately selected from a range of 1.0 to 10 mol, and preferably 1.0 to 3.0 mol, per 1 mol of compound [II-4].

[0593] Examples of radical initiators that can be used in this reaction include azobisisobutyronitrile (AIBN), azobis(cyclohexanecarbonitrile) (ABCN), di-tert-butyl peroxide, tert-butyl hydroperoxide, benzoyl peroxide, etc. The amount of the radical initiator used may be appropriately selected from the range of 0.001 to 0.2 mol, preferably 0.002 to 0.1 mol, per 1 mol of compound [II-4].

[0594] Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, tetrachloromethane, and 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; aromatic hydrocarbons such as benzene and chlorobenzene; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1,000 liters, and preferably 0.2 to 100 liters, per 1 mol of compound [II-4].

[0595] This reaction may be carried out under light irradiation.

[0596] The reaction temperature of this reaction may be selected from any temperature range from 0°C to the reflux temperature of the reaction system, and is preferably in the range of 0°C to 100°C.

[0597] The reaction time for this reaction varies depending on the reaction temperature, reaction substrate, and reaction amount, but is usually from 10 minutes to 72 hours.

[0598] After the reaction is complete, the reaction mixture is poured into water, and the precipitated solid is collected by filtration, or the solid is extracted with an organic solvent and then concentrated, to isolate Compounds [II-5] and [II-6]. The isolated Compounds [II-5] and [II-6] can be further purified, if necessary, by column chromatography, recrystallization, or the like.

[0599] <Production Method 22> Among the intermediates of the compound of the present invention, the compound represented by general formula [II-8] can be produced using the compound represented by general formula [II-6] according to the method consisting of the reaction scheme exemplified below.

[0600]

[0601] (wherein v represents an integer of 1 to 3, and X ４ , R １ , R ２ , and R １０ has the same meaning as above.)

[0602] That is, the compound represented by the general formula [II-8] can be produced by (step 22-1) reacting the compound [II-6] with the compound [V-15] in an appropriate solvent to obtain the compound [II-7], and then (step 22-2) reacting the compound [II-7] with the compound [V-16] in an appropriate solvent in the presence or absence of an appropriate acid catalyst.

[0603] (Step 22-1) Examples of the compound [V-15] that can be used in this reaction include silver nitrate and zinc(II) chloride. The amount of the compound [V-15] used may be appropriately selected from a range of 1.0 to 50 mol, preferably 1.0 to 10 mol, per 1 mol of the compound [II-6].

[0604] Examples of solvents that can be used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, etc.; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, heptane, etc.; aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, etc.; alcohols such as methanol, ethanol, 2-propanol, etc.; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, etc.; nitriles such as acetonitrile, propionitrile, etc.; ketones such as acetone, methyl ethyl ketone, etc.; water, or a mixture thereof. The amount of the solvent used is 0.1 to 1,000 L, preferably 0.2 to 100 L, per 1 mol of Compound [II-6].

[0605] The reaction ...

Claims

1. General formula [I] [In the formula, Q is -NR ａ R ｂ or a nitro group, W represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom (the sulfur atom may be oxidized by one or two oxygen atoms), １ represents an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), -CH ２ - or -NR ｃ - indicates A ２ represents -CH- or a nitrogen atom; R １ is a hydrogen atom, a halogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, or C １ ~C ６ R represents an alkoxy group; ２ and R ３ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, cyano group, formyl group, carboxyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ a cycloalkylaminocarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β, and the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α); ２ and R ３ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 5- or 6-membered ring together with 0 to 1 atom or atomic group selected from １ ~C ６ Alkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group, an oxo group, or an aryl group; ４ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, formyl group, C １ ~C ６ Alkylcarbonyl group, or C １ ~C ６ represents an alkoxycarbonyl group, L represents L-1, L-2, or L-3, R ５ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a cyano C １ ~C ６ Alkyl group, or C ６ ~C １２ Aryl C １ ~C ６ R represents an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α); ６ is a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, or C １ ~C ６ R represents an alkoxy group; ７ is a hydrogen atom, a halogen atom, a hydroxyl group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α); R ８ is a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a nitro group, -CR ｄ R ｅ R ｆ , -OR ｈ , -NR ｉ R ｋ , methyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkenyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, tri(C １ ~C ６ Alkyl)silyl C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (wherein the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C ３ ~C ８ a cycloalkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylthio group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl group, cyanothio group, C １ ~C ６ Alkylcarbonylthio group, aminosulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylthio group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfinyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α); ６ ~C １２ an arylsulfonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylthio group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfinyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfonyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylthio group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylsulfinyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylsulfonyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a formyl group, a carboxyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ a cycloalkylaminocarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β, and the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α, and the amino group may be substituted with a substituent selected from the substituent group γ), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α), -C(═NR ｍ ) R ｎ group, or -C(R ｏ ) = CR ｐ (R ｓ ) group, R ９ is a hydrogen atom, a halogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ R represents an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α); ｘ and R ｙ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ represents an alkyl group, and R ｘ and R ｙ may be taken together to form an oxo group, R ｚ is a hydrogen atom, a halogen atom, or C １ ~C ６ represents an alkyl group, R ａ and R ｂ each independently represents a hydrogen atom, a hydroxyl group, an amino group, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), a formyl group, １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Haloalkylcarbonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), and R ａ and R ｂ are combined to form (=CH)-C １ ~C ６ Alkyl group, (=CH)-C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), or (═CH)—N(C １ ~C ６ Alkyl group) ２ and further, R ａ and R ｂ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a nitrogen-containing 4- to 6-membered ring together with 0 to 1 atom or atomic group selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group, an oxo group, or an aryl group; ｃ is a hydrogen atom, C １ ~C ６ Alkyl group, or C １ ~C ６ represents an alkylcarbonyl group; R ｄ , R ｅ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, or tri(C １ ~C ６ alkyl)silyloxy group, and R ｄ and R ｅ Let's get together =CH ２ and further, R ｄ and R ｅ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 3- to 6-membered ring together with 0 to 2 atoms or atomic groups selected from １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group, an oxo group, or an aryl group; ｆ is a halogen atom, a hydroxy group, a mercapto group, an amino group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ Alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryloxy C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyloxy C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryloxy C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a mercapto C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkylthio C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminosulfonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a cyanothio group, １ ~C ６ Alkyl group, amino C １ ~C ６ Alkyl group, C １ ~C ６ Alkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ Cycloalkylamino C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β, and the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Haloalkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylcarbonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkoxycarbonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylsulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Haloalkylsulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), an aminosulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ) C １ ~C ６ Alkylaminosulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a cyano C １ ~C ６ Alkyl group, formyl C １ ~C ６ Alkyl group, carboxyl group １ ~C ６ Alkyl group, C １ ~C ６ Alkyl carbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxycarbonyl C １ ~C ６ Alkyl group, aminocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Arylaminocarbonyl C １ ~C ６ an alkyl group, (the aryl group may be substituted with one or more substituents selected from the substituent group α, and the amino group may be substituted with a substituent selected from the substituent group γ), a hydroxyaminocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxyaminocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Arylcarbonyl C １ ~C ６ an alkyl group (wherein the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylcarbonyl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclylcarbonyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), an aminothiocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminothiocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), -(C １ ~C ６ alkyl)-C(=NR ｍ ) R ｎ , C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkoxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６ an alkoxy group (wherein the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkoxy group (wherein the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkoxy group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylcarbonyloxy group, C ３ ~C ８ A cycloalkylcarbonyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), an aminocarbonyloxy group, C ６ ~C １２ an aryloxy group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryloxy group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyloxy group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C ３ ~C ８ a cycloalkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylthio group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl group, cyanothio group, C １ ~C ６ Alkylcarbonylthio group, aminosulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylthio group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfinyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylthio group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylsulfinyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylsulfonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ a cycloalkylamino group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β, and the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ haloalkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), aminocarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkylaminocarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkoxycarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group α), C １ ~C ６ an alkylsulfonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ haloalkylsulfonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), aminosulfonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ alkylaminosulfonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), 5- to 12-membered heteroarylamino group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α, and the amino group may be substituted with a substituent selected from the substituent group γ), formyl group, carboxyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C ６ ~C １２ an aryloxycarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryloxycarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), an aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a hydroxyaminocarbonyl group, １ ~C ６ an alkoxyaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), a 5- to 12-membered heteroarylaminocarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), a 3- to 6-membered heterocyclylaminocarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), an aminothiocarbonyl group, １ ~C ６ an alkylaminothiocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylcarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α), or -C(=NR ｍ ) R ｎ R represents a group; ｈ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryloxy C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryloxy C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyloxy C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a mercapto C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkylthio C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a formyl group, １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α, and the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α), -N=CH-(C １ ~C ６ alkyl group), or -N=C(C １ ~C ６ Alkyl group) ２ Indicates R ｉ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a cyano C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ R represents an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α); ｋ is a hydrogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (wherein the aryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a formyl group, １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylcarbonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, cyano C １ ~C ６ Alkylcarbonyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkylcarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ alkylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylcarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α), and further R ｉ and R ｋ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a nitrogen-containing 4- to 6-membered ring together with 0 to 1 atom or atomic group selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ R may be substituted by one or more chemically acceptable substituents selected from an alkylcarbonylamino group (the amino group may be substituted by a substituent selected from the substituent group γ) or an oxo group; ｍ is a hydroxy group, an amino group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), or C １ ~C ６ R represents an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ); ｎ is a hydrogen atom, a halogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α); R ｏ is a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, or C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α); R ｐ is a hydrogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, or C １ ~C ６ R represents an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ); ｓ is a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, or C １ ~C ６ represents an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ); ｐ and R ｓ may be bonded to each other to form a 5- or 6-membered ring together with 0 to 2 atoms or atomic groups selected from carbon atoms, oxygen atoms, and sulfur atoms (the sulfur atoms may be oxidized with 1 or 2 oxygen atoms), and the 5- or 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group, an oxo group, or an aryl group; ｕ is a hydrogen atom or C １ ~C ６ The substituent group α represents a halogen atom, a hydroxy group, a mercapto group, an amino group, a cyano group, a nitro group, １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a halocycloalkyl group (the halocycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (wherein the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６ Alkoxy group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ alkoxy group, cyano group, or the like; ２ ~C ６ Alkenyloxy group, C ２ ~C ６ Alkynyloxy group, tri(C １ ~C ６ alkyl)silyloxy group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ An aryl group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ) and a cyano group); a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the heteroaryl group, １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ Alkylamino group, di(C １ ~C ６ an oxo group, or -C(=NR ｍ ) R ｎ The substituent group β represents a halogen atom, a hydroxy group, an amino group, a cyano group, a C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C １ ~C ６ haloalkyl groups, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ An aryl group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ) and a cyano group); a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the heteroaryl group, １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ Alkylamino group, di(C １ ~C ６ a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from a halogen atom, a C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with a substituent selected from the substituent group γ) or a cyano group, １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C １ ~C ６ haloalkyl groups, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ haloalkylcarbonyl group, or C １ ~C ６ [0013] (representing an alkoxycarbonyl group) or a salt thereof as an active ingredient.

2. General formula [I] [In the formula, Q is -NR ａ R ｂ or a nitro group, W represents an oxygen atom or a sulfur atom, Y represents an oxygen atom or a sulfur atom (the sulfur atom may be oxidized by one or two oxygen atoms), １ represents an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), -CH ２ - or -NR ｃ - indicates A ２ represents -CH- or a nitrogen atom; R １ is a hydrogen atom, a halogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, or C １ ~C ６ R represents an alkoxy group; ２ and R ３ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, cyano group, formyl group, carboxyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ a cycloalkylaminocarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β, and the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α); ２ and R ３ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 5- or 6-membered ring together with 0 to 1 atom or atomic group selected from １ ~C ６ Alkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group, an oxo group, or an aryl group; ４ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, formyl group, C １ ~C ６ Alkylcarbonyl group, or C １ ~C ６ represents an alkoxycarbonyl group, L represents L-1, L-2, or L-3, R ５ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a cyano C １ ~C ６ Alkyl group, or C ６ ~C １２ Aryl C １ ~C ６ R represents an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α); ６ is a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, methoxy group, or C ３ ~C ６ R represents an alkoxy group; ７ is a hydrogen atom, a halogen atom, a hydroxyl group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α); R ８ is a hydroxy group, a mercapto group, a cyano group, -CR ｄ R ｅ R ｆ , -OR ｈ , -NR ｉ R ｋ , C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkenyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, tri(C １ ~C ６ Alkyl)silyl C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (wherein the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C ３ ~C ８ a cycloalkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylthio group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl group, cyanothio group, C １ ~C ６ Alkylcarbonylthio group, aminosulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylthio group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfinyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α); ６ ~C １２ an arylsulfonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylthio group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfinyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 5- to 12-membered heteroarylsulfonyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylthio group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylsulfinyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a 3- to 6-membered heterocyclylsulfonyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α), a formyl group, a carboxyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C ２ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ a cycloalkylaminocarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β, and the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α, and the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α), -C(═NR ｍ ) R ｎ group, or -C(R ｏ ) = CR ｐ (R ｓ ) group, R ９ is a hydrogen atom, a halogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ R represents an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α); ｘ and R ｙ are each independently a hydrogen atom, a halogen atom, or C １ ~C ６ represents an alkyl group, and R ｘ and R ｙ may be taken together to form an oxo group, R ｚ is a hydrogen atom, a halogen atom, or C １ ~C ６ represents an alkyl group, R ａ is a hydrogen atom, a hydroxyl group, an amino group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ alkyl group, 5- to 12-membered heteroaryl C1-C6 alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), 3- to 6-membered heterocyclyl C1-C6 alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), a formyl group, １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Haloalkylcarbonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), or a 3- to 6-membered heterocyclyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α); R ｂ represents a hydrogen atom, and R ａ and R ｂ are combined to form (=CH)-C １ ~C ６ Alkyl group, (=CH)-C ６ ~C １２ an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), or ═CH—N(C １ ~C ６ Alkyl group) ２ R ｃ is a hydrogen atom, C １ ~C ６ Alkyl group, or C １ ~C ６ represents an alkylcarbonyl group; R ｄ , R ｅ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, or tri(C １ ~C ６ alkyl)silyloxy group, and R ｄ and R ｅ Let's get together =CH ２ and further, R ｄ and R ｅ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a 3- to 6-membered ring together with 0 to 2 atoms or atomic groups selected from １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group, an oxo group, or an aryl group; ｆ is a chlorine atom, a bromine atom, an iodine atom, a hydroxyl group, a mercapto group, an amino group, a cyano group, a nitro group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ Alkynyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryloxy C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyloxy C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryloxy C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a mercapto C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkylthio C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminosulfonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a cyanothio group, １ ~C ６ Alkyl group, amino C １ ~C ６ Alkyl group, C １ ~C ６ Alkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ Cycloalkylamino C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β, and the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Haloalkylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylcarbonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkoxycarbonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylsulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Haloalkylsulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), an aminosulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ) C １ ~C ６ Alkylaminosulfonylamino C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a cyano C １ ~C ６ Alkyl group, formyl C １ ~C ６ Alkyl group, carboxyl group １ ~C ６ Alkyl group, C １ ~C ６ Alkyl carbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxycarbonyl C １ ~C ６ Alkyl group, aminocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Arylaminocarbonyl C １ ~C ６ an alkyl group, (the aryl group may be substituted with one or more substituents selected from the substituent group α, and the amino group may be substituted with a substituent selected from the substituent group γ), a hydroxyaminocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxyaminocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ Arylcarbonyl C １ ~C ６ an alkyl group, (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylcarbonyl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclylcarbonyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), an aminothiocarbonyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylaminothiocarbonyl C １ ~C ６ an alkyl group (the amino group may be substituted with a substituent selected from the substituent group γ), -(C １ ~C ６ alkyl)-C(=NR ｍ ) R ｎ , C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkoxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６ an alkoxy group (wherein the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkoxy group (wherein the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkoxy group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylcarbonyloxy group, C ３ ~C ８ A cycloalkylcarbonyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), an aminocarbonyloxy group, C ６ ~C １２ an aryloxy group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryloxy group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyloxy group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C ３ ~C ８ a cycloalkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a cycloalkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylthio group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylsulfinyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkyl C １ ~C ６ an alkylsulfonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylthio group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl sulfonyl group, cyanothio group, C １ ~C ６ Alkylcarbonylthio group, aminosulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylthio group (the aryl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an arylsulfinyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α); ６ ~C １２ an arylsulfonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylthio group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylsulfinyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylsulfonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C ３ ~C ８ a cycloalkylamino group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β, and the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ haloalkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), aminocarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkylaminocarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkoxycarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group α), C １ ~C ６ an alkylsulfonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ haloalkylsulfonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), aminosulfonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ alkylaminosulfonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), 5- to 12-membered heteroarylamino group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α, and the amino group may be substituted with a substituent selected from the substituent group γ), formyl group, carboxyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, C ６ ~C １２ an aryloxycarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryloxycarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), an aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a hydroxyaminocarbonyl group, １ ~C ６ an alkoxyaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), a 5- to 12-membered heteroarylaminocarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), a 3- to 6-membered heterocyclylaminocarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from substituent group α, and the amino group may be substituted with a substituent selected from substituent group γ), an aminothiocarbonyl group, １ ~C ６ an alkylaminothiocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylcarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α), or -C(=NR ｍ ) R ｎ R represents a group; ｈ is a hydrogen atom, C ２ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C ６ ~C １２ Aryloxy C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryloxy C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyloxy C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a mercapto C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkylthio C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfinyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ Cycloalkylsulfonyl C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkylsulfonyl C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a formyl group, １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylaminocarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α, and the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α), -N=CH-(C １ ~C ６ alkyl group), or -N=C(C １ ~C ６ Alkyl group) ２ Indicates, R ｉ is a hydrogen atom, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), a cyano C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ R represents an aryl group (the aryl group may be substituted with one or more substituents selected from the substituent group α) or a 5- to 12-membered heteroaryl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α); ｋ is a hydrogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, hydroxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyloxy C １ ~C ６ an alkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylthio C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfinyl C １ ~C ６ Alkyl group, C １ ~C ６ Alkylsulfonyl C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkyl group (wherein the aryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclyl C １ ~C ６ an alkyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ an alkyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ an alkylaminosulfonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), a formyl group, １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkylcarbonyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkylcarbonyl group, cyano C １ ~C ６ Alkylcarbonyl group, C ６ ~C １２ Aryl C １ ~C ６ an alkylcarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl C １ ~C ６ alkylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), 3- to 6-membered heterocyclyl C １ ~C ６ an alkylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an arylcarbonyl group (the aryl group may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroarylcarbonyl group (the heteroaryl group may be substituted with one or more substituents selected from the substituent group α), a 3- to 6-membered heterocyclylcarbonyl group (the heterocyclyl group may be substituted with one or more substituents selected from the substituent group α), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α), and further R ｉ and R ｋ are mutually bonded to a carbon atom, an oxygen atom, a sulfur atom (the sulfur atom may be oxidized with one or two oxygen atoms), and NR ｕ may form a nitrogen-containing 4- to 6-membered ring together with 0 to 1 atom or atomic group selected from the group consisting of a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ R may be substituted by one or more chemically acceptable substituents selected from an alkylcarbonylamino group (the amino group may be substituted by a substituent selected from the substituent group γ) or an oxo group; ｍ is a hydroxy group, an amino group, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), or C １ ~C ６ R represents an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ); ｎ is a hydrogen atom, a halogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α); R ｏ is a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, or C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ an aryl group (which may be substituted with one or more substituents selected from the substituent group α), a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the substituent group α), or a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from the substituent group α); R ｐ is a hydrogen atom, a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, or C １ ~C ６ R represents an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ); ｓ is a cyano group, C １ ~C ６ Alkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, or C １ ~C ６ represents an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ); ｐ and R ｓ may be bonded to each other to form a 5- or 6-membered ring together with 0 to 2 atoms or atomic groups selected from carbon atoms, oxygen atoms, and sulfur atoms (the sulfur atoms may be oxidized with 1 or 2 oxygen atoms), and the 5- or 6-membered ring is C １ ~C ６ Alkyl group, C １ ~C ６ R may be substituted with one or more chemically acceptable substituents selected from an alkoxy group, an oxo group, or an aryl group; ｕ is a hydrogen atom or C １ ~C ６ The substituent group α represents a halogen atom, a hydroxy group, a mercapto group, an amino group, a cyano group, a nitro group, １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ a cycloalkyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C ３ ~C ８ a halocycloalkyl group (the halocycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C ２ ~C ６ Alkenyl group, C ２ ~C ６ Alkynyl group, C ３ ~C ８ Cycloalkyl C ２ ~C ６ an alkynyl group (wherein the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxy group, C ３ ~C ８ a cycloalkyloxy group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Haloalkyloxy group, C １ ~C ６ Alkoxy C １ ~C ６ Alkoxy group, C ６ ~C １２ Aryl C １ ~C ６ Alkoxy group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ alkoxy group, cyano group, or the like; ２ ~C ６ Alkenyloxy group, C ２ ~C ６ Alkynyloxy group, tri(C １ ~C ６ alkyl)silyloxy group, C １ ~C ６ Alkylthio group, C １ ~C ６ Alkylsulfinyl group, C １ ~C ６ Alkylsulfonyl group, C １ ~C ６ Haloalkylthio group, C １ ~C ６ Haloalkylsulfinyl group, C １ ~C ６ Haloalkylsulfonyl group, C １ ~C ６ an alkylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylcarbonyl group, C ３ ~C ８ a cycloalkylcarbonyl group (the cycloalkyl group may be substituted with a substituent selected from the substituent group β), C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ An aryl group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ) and a cyano group); a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the heteroaryl group, １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ Alkylamino group, di(C １ ~C ６ an oxo group, or -C(=NR ｍ ) R ｎ The substituent group β represents a halogen atom, a hydroxy group, an amino group, a cyano group, a C １ ~C ６ Alkyl group, C ３ ~C ８ Cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C １ ~C ６ haloalkyl groups, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Alkoxy group, C １ ~C ６ an alkylcarbonylamino group (the amino group may be substituted with a substituent selected from the substituent group γ), C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ Alkoxycarbonyl group, aminocarbonyl group, C １ ~C ６ an alkylaminocarbonyl group (the amino group may be substituted with a substituent selected from the substituent group γ), C ６ ~C １２ An aryl group (the aryl group is a halogen atom, C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with one or more substituents selected from the substituent group γ) and a cyano group); a 5- to 12-membered heteroaryl group (which may be substituted with one or more substituents selected from the heteroaryl group, １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ Alkylamino group, di(C １ ~C ６ a 3- to 6-membered heterocyclyl group (which may be substituted with one or more substituents selected from a halogen atom, a C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C １ ~C ６ Alkoxy group, amino group, C １ ~C ６ an alkylamino group (which may be substituted with a substituent selected from the substituent group γ) or a cyano group, １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyl group, C ３ ~C ８ Cycloalkyl group (the cycloalkyl group is C １ ~C ６ Alkyl group, or C １ ~C ６ haloalkyl groups, C １ ~C ６ Alkoxy C １ ~C ６ Alkyl group, C １ ~C ６ Haloalkyloxy C １ ~C ６ Alkyl group, cyano C １ ~C ６ Alkyl group, C １ ~C ６ Alkylcarbonyl group, C １ ~C ６ haloalkylcarbonyl group, or C １ ~C ６ [0023] (representing an alkoxycarbonyl group) or a salt thereof.

3. An agricultural and horticultural plant disease control agent comprising the nicotinamide derivative or its salt according to claim 2 as an active ingredient.

4. An agricultural and horticultural plant disease control agent according to claim 1 or 3, wherein the plant disease is caused by a pathogenic fungus.

5. The agricultural and horticultural plant disease control agent according to claim 4, wherein the plant disease is classified into any of the kingdoms Fungi, Stramenopila, Rhizaria, and Bacteria.

6. The agricultural and horticultural plant disease control agent according to claim 4, wherein the plant disease is classified as Stramenopila.

7. An agricultural or horticultural plant disease control agent comprising the nicotinamide derivative or its salt according to claim 2 and an agriculturally acceptable carrier.

8. A method for controlling plant diseases by using an effective amount of the nicotinamide derivative or its salt according to claim 2 by spraying, soil application, surface application, seed treatment, immersion, poison bait or fumigation.

9. The method according to claim 8, which comprises spraying a useful plant or a part of a useful plant, or a place where the useful plant is growing, or treating seeds of a useful plant.

10. The method according to claim 8, wherein the plant disease is caused by a pathogenic fungus.

11. The method according to claim 9, wherein the plant disease is caused by a pathogenic fungus.

12. The method of claim 10, wherein the plant disease is classified into any of the kingdoms Fungi, Stramenopila, Rhizaria, and Bacteria.

13. The method of claim 11, wherein the plant disease is classified into any of the kingdoms Fungi, Stramenopile, Rhizaria, and Bacteria.

14. The method according to claim 10, wherein the early stage plant disease is classified as Stramenopila.

15. The method according to claim 11, wherein the early stage plant disease is classified as Stramenopila.

16. Use of the nicotinamide derivative or a salt thereof according to claim 2 as an agricultural or horticultural plant disease control agent for useful plants.

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