Nicotinamide derivative and agricultural and horticultural plant disease control agent

Abstract

Provided is an excellent agricultural and horticultural plant disease control agent. A nicotinamide derivative represented by general formula [I] or a salt thereof: (In general formula [I], Q represents-NRaRb or the like, W represents an oxygen atom or the like, Y represents an oxygen atom or the like, A1 represents an oxygen atom or the like, A2 represents-CH-or a nitrogen atom, R1 represents a hydrogen atom or the like, R2 and R3 each independently represent a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or the like, L represents L-1, L-2 or L-3, R5 represents a C1-C6 alkyl group or the like, R6 represents a hydrogen atom or the like, and R7 represents a hydrogen atom or the like; r8 represents a hydrogen atom, a halogen atom, a C1-C6 alkoxy group or the like, R9 represents a hydrogen atom or the like, Rx and Ry each independently represent a hydrogen atom, a halogen atom or the like, Rz represents a hydrogen atom or the like, and Ra and Rb each independently represent a hydrogen atom, a C1-C6 alkyl group or the like. And an agricultural and horticultural plant disease control agent containing the same as an active ingredient.

Description

Technical Field

[0001] This invention relates to a novel nicotinamide derivative or its salt, and an agricultural and horticultural plant disease control agent containing a nicotinamide derivative or its salt as an active ingredient. Background Technology

[0002] Patent Document 1 describes a nicotinamide derivative as a compound useful for treating angiogenesis-related diseases, but does not describe its activity in controlling plant diseases. Furthermore, the substituent at the 2-position of the nicotinic portion is limited to a 4-6 membered heterocyclic amino group, a substituted aryl amino group, or a 9-14 membered bicyclic or tricyclic heterocyclic amino group.

[0003] Patent document 2 describes a nicotinamide derivative as a nitric oxide production promoter, but does not describe its plant disease control activity.

[0004] [Previous Technical Documents] [Patent Literature] Patent Document 1: International Publication No. 2002 / 068406 Patent Document 2: Japanese Patent Application Publication No. 2007-186435 Summary of the Invention When cultivating useful crops, large amounts of plant disease control agents are used to treat plant diseases originating from pathogens.

[0005] However, previous plant disease control agents have not been effective enough in controlling plant diseases originating from pathogens, or pathogens have developed resistance to the agents, thus limiting their use due to the plant diseases they originate from. In addition, from the perspective of causing phytotoxicity and pollution to plants, or toxicity to humans, livestock and fish, and environmental impact, they may not have satisfactory performance.

[0006] Therefore, there is a strong demand for the development of a plant disease control agent that has fewer of the aforementioned drawbacks and can be used safely.

[0007] The inventors of this case conducted repeated and in-depth research and found that the agent containing the nicotinamide derivative or its salt as shown in the following formula [I] as the active ingredient has a high control effect on plant diseases originating from pathogens in the cultivation site of useful crops, thus completing the present invention.

[0008] That is, the gist of the present invention is as follows.

[0009] (1) An agricultural and horticultural plant disease control agent, characterized in that it contains a nicotinamide derivative or its salt represented by general formula [I] as an active ingredient. [Chemistry 1] [In the formula, Q indicates -NRa R b Or nitro, W represents an oxygen atom or a sulfur atom. Y represents an oxygen atom or a sulfur atom (the sulfur atom can be oxidized by one or two oxygen atoms). A 1 This represents an oxygen atom, a sulfur atom (which can be oxidized by one or two oxygen atoms), -CH2-, or -NR. c , A 2 Represents -CH- or nitrogen atom, R 1 This represents hydrogen atoms, halogen atoms, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl or C1~C6 alkoxy groups, R 2 and R 3 Each of these elements independently represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylthio, C1-C6 alkyl, C1-C6 alkylsulfinyl, C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C1-C6 alkylamino (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (substituent with one or more substituents), C1-C6 alkoxy, cyano, formyl, carboxyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, amino carbonyl, C1-C6 alkylamino carbonyl (the amino group can be selected from the substituent group) c Substituents in the group), C3~C8 cycloalkylaminocarbonyl (the cycloalkyl group can be selected from the substituent group) β The amino group can be substituted with a substituent selected from the group consisting of substituents. c Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α(one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (more than one substituent in R), further, R 2 With R 3 They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u The 0 to 1 atoms or groups of atoms in the ring together form a 5 to 6-membered ring, which can be replaced by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 alkoxy, or oxo groups. R 4 This represents a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group include C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, formyl, C1-C6 alkyl carbonyl, or C1-C6 alkoxy carbonyl. L represents L-1, L-2, or L-3. R 5 This represents a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarbonyl, C6-C6 alkylyl, C6-C6 alkylyl, C2-C6 alkylyl ... 12 aryl (which can be selected from the substituent group) α (one or more substituents in the group), cyano C1~C6 alkyl or C6~C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (with one or more substituents in the group) R 6 This represents hydrogen atoms, halogen atoms, hydroxyl groups, cyano groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl or C1~C6 alkoxy groups, R 7 This represents hydrogen atoms, halogen atoms, hydroxyl groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which can be selected from the substituent group) α(one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) R 8 Represents hydrogen atom, halogen atom, hydroxyl group, mercapto group, cyano group, nitro group, -CR d R e R f -OR h -NR i R k methyl, C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in the group (C3-C8 cycloalkenyl, C2-C6 alkenyl, C2-C6 ynyl, tris(C1-C6 alkyl)silylC2-C6 ynyl, C3-C8 cycloalkylC2-C6 ynyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C1~C6 alkylthio, C1~C6 alkylsulfinyl, C1~C6 alkylsulfonyl, C3~C8 cycloalkylthio (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl group (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C3~C8 cycloalkylsulfonyl groups (the cycloalkyl group can be selected from the substituent group) β Substituents in the group (e.g., C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkoxy-C1-C6 alkylthio, C1-C6 alkoxy-C1-C6 alkylsulfinyl, C1-C6 alkoxy-C1-C6 alkylsulfonyl, cyanothio, C1-C6 alkylcarbonylthio, aminosulfonyl, C1-C6 alkylaminosulfonyl (the amino group can be selected from the substituent group)). c Substituents in (C6~C) 12 arylthio (the aryl group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfinyl (the aryl group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfonyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylthio groups (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylsulfinyl group (the heteroaryl group can be selected from the substituent group)α (one or more substituents), 5-12 membered heteroarylsulfonyl groups (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3- to 6-membered heterocyclic thio groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic sulfinyl group (this heterocyclic group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic sulfonyl group (this heterocyclic group can be selected from the substituent group) α (substituents of one or more substituents), formyl group, carboxyl group, C1-C6 alkyl carbonyl group, C3-C8 cycloalkyl carbonyl group (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C1~C6 alkoxy-C1~C6 alkyl carbonyl, C1~C6 alkoxy carbonyl, amino carbonyl, C1~C6 alkylamino carbonyl (the amino group can be selected from the substituent group) c Substituents in the group), C3~C8 cycloalkylaminocarbonyl (the cycloalkyl group can be selected from the substituent group) β The amino group can be substituted with a substituent selected from the group consisting of substituents. c Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in the group), 3-6 membered heterocyclic carbonyl groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (substituents of one or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (substitution of one or more substituents), -C (=NR) m )R n base or -C(R) o )=CR p (R s )base, R 9 This represents hydrogen atoms, halogen atoms, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which can be selected from the substituent group) α(substituent with one or more substituents) or 5-12 heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (with one or more substituents in the group) R x and R y Each independently represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group; further, R x and R y They can combine to form oxygen groups. R z Indicates hydrogen atom, halogen atom, or C1~C6 alkyl group. R a and R b Each of these elements independently represents a hydrogen atom, hydroxyl group, amino group, C1-C6 alkyl group, or C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl, C6-C6) 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, C1-C6 alkylamino (the amino group can be selected from the substituent group) c Substituents in the group include: formyl group, C1-C6 alkyl carbonyl group, C1-C6 haloalkyl carbonyl group, C1-C6 alkoxy C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, amino carbonyl group, and C1-C6 alkylamino carbonyl group (the amino group can be selected from the substituent group group). c Substituents in the group), 3-6 membered heterocyclic groups (the heterocyclic group can be selected from the substituent group group) α (more than one substituent in it), in addition, R a and R b They can form (=CH)-(C1~C6 alkyl) and (=CH)-(C6~C6 alkyl) together. 12 (The aryl group can be selected from the substituent group) α (substituents of one or more groups) or (=CH)-N(C1~C6 alkyl)2, further, R a With R b They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. uThe 0 to 1 atoms or groups of atoms together form a nitrogen-containing 4 to 6-membered ring, which can be replaced by one or more chemically acceptable substituents selected from halogen atoms, C1 to C6 alkyl groups, C1 to C6 haloalkyl groups, C1 to C6 alkoxy groups, or oxo groups. R c Represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 alkyl carbonyl group. R d R e Each of these groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy or tris(C1-C6 alkyl)silyloxy, or R d and R e They can form =CH2 together, and further, R d With R e They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u The 0 to 2 atoms or groups together form a 3 to 6-membered ring, which can be replaced by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 haloalkyl, C1 to C6 alkoxy, or oxo groups. R f This indicates halogen atoms, hydroxyl groups, mercapto groups, amino groups, cyano groups, nitro groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 ynyl, C3~C8 cycloalkyl, C2~C6 ynyl (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C8 cycloalkyloxy C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C6-C6 alkyl) 12 aryloxy C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic oxy-C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryloxy C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α(One or more substituents), mercapto C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C3-C8 cycloalkylthio C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 haloalkylthio-C1-C6 alkyl, C1-C6 haloalkylsulfinyl-C1-C6 alkyl, C1-C6 haloalkylsulfonyl-C1-C6 alkyl, C1-C6 alkylaminosulfonyl-C1-C6 alkyl (the amino group can be selected from the substituent group)). c Substituents in (e.g., cyanothio C1-C6 alkyl, amino C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl (the amino group can be selected from the substituent group)). c (substituents in the group), C3~C8 cycloalkylamino C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β The amino group can be substituted with a substituent selected from the group consisting of substituents. c Substituents in (C1-C6 alkyl halogenated amino groups) (the amino group can be selected from the substituent group) c (substituents in the group), C1~C6 alkyl carbonyl amino C1~C6 alkyl (the amino group can be selected from the substituent group) c (substituents in the group), C1~C6 alkoxycarbonyl amino C1~C6 alkyl (the amino group can be selected from the substituent group) c (substituents in the group), C1~C6 alkylsulfonylamino C1~C6 alkyl (the amino group can be selected from the substituent group) c Substituents in (C1-C6 haloalkylsulfonylamino C1-C6 alkyl (the amino group can be selected from the substituent group) c Substituents in (e.g., aminosulfonylamino C1-C6 alkyl, where the amino group can be selected from the substituent group) c (substituents in the group), C1~C6 alkylaminosulfonylaminoC1~C6 alkyl (the amino group can be selected from the substituent group) c Substituents in the group (e.g., cyano C1-C6 alkyl, formyl C1-C6 alkyl, carboxyl C1-C6 alkyl, C1-C6 alkyl carbonyl C1-C6 alkyl, C1-C6 alkoxy carbonyl C1-C6 alkyl, amino carbonyl C1-C6 alkyl, C1-C6 alkyl amino carbonyl C1-C6 alkyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 arylaminocarbonyl C1~C6 alkyl (the aryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in (e.g., hydroxyaminocarbonyl C1-C6 alkyl, C1-C6 alkoxyaminocarbonyl C1-C6 alkyl) (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 Aryl carbonyl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylcarbonyl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3-6 membered heterocyclic carbonyl C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (substituent with one or more substituents), aminothiocarbonyl C1-C6 alkyl, C1-C6 alkylaminothiocarbonyl C1-C6 alkyl (the amino group can be selected from the substituent group) c Substituents in (C1~C6 alkyl)-C (=NR) m )R n C6~C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, C3-C8 cycloalkyloxy (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C1-C6 haloalkyloxy groups, C3-C8 cycloalkyl groups, and C1-C6 alkoxy groups (the cycloalkyl group can be selected from the substituent group). β (substituents in C1-C6 alkoxy groups, C1-C6 alkoxy groups, C6-C6 alkoxy groups) 12 Aryl C1~C6 alkoxy (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkoxy groups (the heteroaryl group can be selected from the substituent group) α (One or more substituents in the group), 3-6 membered heterocyclic C1-C6 alkoxy groups (the heterocyclic group can be selected from the substituent group group) α(one or more substituents), C1-C6 alkyl carbonyloxy group, C3-C8 cycloalkyl carbonyloxy group (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), aminocarbonyloxy group, C6~C 12 aryloxy group (the aryl group can be selected from the substituent group) α (one or more substituents in the group), 5-12 membered heteroaryloxy groups (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic oxygen groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylthio (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl group (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C3~C8 cycloalkylsulfonyl groups (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C1~C6 haloalkylthio, C1~C6 haloalkylsulfinyl, C1~C6 haloalkylsulfonyl, C3~C8 cycloalkyl C1~C6 alkylthio (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl C1~C6 alkylsulfinyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C3-C8 cycloalkyl C1-C6 alkylsulfonyl group) (the cycloalkyl group can be selected from the substituent group) β (Substituents in the group), C1~C6 alkoxy-C1~C6 alkylthio, C1~C6 alkoxy-C1~C6 alkylsulfinyl, C1~C6 alkoxy-C1~C6 alkylsulfonyl, cyanothio, C1~C6 alkylcarbonylthio, aminosulfonyl, C1~C6 alkylaminosulfonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 arylthio (the aryl group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfinyl (the aryl group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfonyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylthio groups (the heteroaryl group can be selected from the substituent group) α(one or more substituents), 5-12 membered heteroarylsulfinyl group (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylsulfonyl groups (the heteroaryl group can be selected from the substituent group) α (one or more substituents in the group), C1-C6 alkylamino (the amino group can be selected from the substituent group) c Substituents in (C3-C8 cycloalkylamino groups, where the cycloalkyl group can be selected from the substituent group) β The amino group can be substituted with a substituent selected from the group consisting of substituents. c Substituents in (C1-C6 haloalkylamino groups, where the amino group can be selected from the substituent group) c Substituents in (substituents), aminocarbonylamino (the amino group can be selected from the substituent group) c Substituents in (C1-C6 alkylamino carbonylamino groups) (the amino group can be selected from the substituent group) c Substituents in (C1-C6 alkoxycarbonyl amino groups, which can be selected from the substituent group) α Substituents in (C1-C6 alkylsulfonylamino groups, where the amino group can be selected from the substituent group) c Substituents in (C1-C6 haloalkylsulfonylamino groups, where the amino group can be selected from the substituent group group) c (substituents in the group), aminosulfonylamino (the amino group can be selected from the substituent group) c Substituents in (C1-C6 alkylaminosulfonylamino groups, where the amino group can be selected from the substituent group) c Substituents in the group), 5-12 membered heteroarylamino groups (the heteroaryl group can be selected from the substituent group group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in the group include: formyl group, carboxyl group, C1-C6 alkyl carbonyl group, and C3-C8 cycloalkyl carbonyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkoxy-C1-C6 alkyl-carbonyl, C1-C6 alkoxy-carbonyl, C6-C6) 12 aryloxycarbonyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryloxycarbonyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), amino carbonyl, C1-C6 alkylamino carbonyl (the amino group can be selected from the substituent group) c Substituents in (e.g., hydroxyaminocarbonyl, C1-C6 alkoxyaminocarbonyl, where the amino group can be selected from the substituent group) cSubstituents in (C6~C) 12 arylaminocarbonyl (the aryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in the group), 5-12 membered heteroarylaminocarbonyl (the heteroaryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in the group), 3-6 membered heterocyclic amino carbonyl groups (the heterocyclic group can be selected from the substituent group group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in (e.g., aminothiocarbonyl, C1-C6 alkylaminothiocarbonyl, where the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl carbonyl (the aryl group can be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylcarbonyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3- to 6-membered heterocyclic carbonyl groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (substituents of one or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents in) or -C (=NR) m )R n base, R h This represents a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C8 cycloalkyloxy C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C6-C6 alkyl) 12 aryloxy C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryloxy C1-C6 alkyl (the heteroaryl group can be selected from the substituent group)α (one or more substituents), 3-6 membered heterocyclic oxy-C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (One or more substituents), mercapto C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C3-C8 cycloalkylthio C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 haloalkylthio-C1-C6 alkyl, C1-C6 haloalkylsulfinyl-C1-C6 alkyl, C1-C6 haloalkylsulfonyl-C1-C6 alkyl, C6-C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylaminosulfonyl (the amino group can be selected from the substituent group) c (substituents in the group), formyl group, C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, amino carbonyl group, C1-C6 alkylamino carbonyl group (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (substituents of one or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (substituents of one or more substituents), -N=CH-(C1~C6 alkyl) or -N=C(C1~C6 alkyl)2, R iThis represents a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in (e.g., cyano C1-C6 alkyl, C6-C6 alkyl) 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents) or 3- to 6-membered heterocyclic C1- to C6 alkyl groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) R k This represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C8 cycloalkyloxy C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C1-C6 alkylthiolated C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, cyano C1-C6 alkyl, C6-C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl (the amino group can be selected from the substituent group) c Substituents in the group (e.g., formyl group, C1-C6 alkyl carbonyl group, C3-C8 cycloalkyl carbonyl group, where the cycloalkyl group can be selected from the substituent group group) β Substituents in (C1-C6 haloalkyl carbonyl, C1-C6 alkoxy C1-C6 alkyl carbonyl, cyano C1-C6 alkyl carbonyl, C6-C6 alkyl carbonyl) 12 Aryl C1~C6 alkyl carbonyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl carbonyl (the heteroaryl group can be selected from the substituent group) α(substituent with one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl carbonyl (this heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl carbonyl (the aryl group can be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylcarbonyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3- to 6-membered heterocyclic carbonyl groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) Furthermore, R i With R k They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u The 0 to 1 atoms or groups of atoms in the ring together form a nitrogen-containing 4 to 6-membered ring, which can be selected from halogen atoms, C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 alkyl carbonyl, C1 to C6 alkoxy carbonyl, amino carbonyl, and C1 to C6 alkyl amino carbonyl (the amino group can be selected from the substituent group). c Substituents in (C1-C6 alkyl carbonyl amino groups, where the amino group can be selected from the substituent group) c (Substituent substitution in the group) or more than one chemically acceptable substituent substitution in the oxo group. R m This indicates hydroxyl, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, and C3-C8 cycloalkyloxy (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkyloxy groups, C1-C6 alkylamino groups, where the amino group can be selected from the substituent group group) c (substituents in the group) or C1~C6 alkyl carbonyl amino (the amino group can be selected from the substituent group) c (substituents in the text) R nThis represents hydrogen atoms, halogen atoms, cyano groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) R o This indicates cyano, C1-C6 alkyl, or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarbonyl, C3-C8 cycloalkylcarbonyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl (the amino group can be selected from the substituent group)). c Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) R p This represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1~C6 haloalkyl, C1~C6 alkoxy, C1~C6 alkyl, C1~C6 alkoxy, C1~C6 alkyl carbonyl, C3~C8 cycloalkyl carbonyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C1~C6 alkoxycarbonyl or C1~C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c (substituents in the text) R s This indicates cyano, C1-C6 alkyl, or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). βSubstituents in the group), C1~C6 haloalkyl, C1~C6 alkoxy, C1~C6 alkyl, C1~C6 alkoxy, C1~C6 alkyl carbonyl, C3~C8 cycloalkyl carbonyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C1~C6 alkoxycarbonyl or C1~C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c (substituents in the text) Furthermore, R p With R s They can bond with each other to form a 5-6 membered ring with 0-2 atoms or groups selected from carbon, oxygen, and sulfur (which can be oxidized by one or two oxygen atoms). This 5-6 membered ring can be substituted by one or more chemically acceptable substituents selected from C1-C6 alkyl, C1-C6 alkoxy, or oxo groups. R u Indicates a hydrogen atom or a C1-C6 alkyl group. Substitute basis set α This indicates halogen atoms, hydroxyl groups, mercapto groups, amino groups, cyano groups, nitro groups, C1-C6 alkyl groups, C1-C6 haloalkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C3~C8 halocycloalkyl groups (the halocycloalkyl group can be selected from the substituent group) β Substituents in the group (C1-C6 alkoxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C8 cycloalkyl, C2-C6 ynyl (the cycloalkyl group can be selected from the substituent group)). β Substituents in the group), C1-C6 alkoxy groups, C3-C8 cycloalkyloxy groups (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl oxy, C1-C6 alkoxy, C6-C6 alkoxy) 12 aryl C1-C6 alkoxy (the aryl group may be substituted by one or more substituents selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, cyano), C2-C6 alkenoxy, C2-C6 alkynoxy, tris(C1-C6 alkyl)silyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino (the amino group may be selected from the substituent group) c Substituents in (C1-C6 alkyl carbonyl amino groups, where the amino group can be selected from the substituent group) c Substituents in the group), C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group can be selected from the substituent group)β Substituents in the group), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl (the aryl group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (substituents in the group), substitution of one or more substituents in the cyano group), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, C1-C6 alkylamino groups (the amino group can be selected from the substituent group group) c Substituents in the group), substitution of one or more substituents in the cyano group), oxo group or -C (=NR) m )R n base, Substitute basis set β This indicates a halogen atom, hydroxyl group, amino group, cyano group, C1-C6 alkyl group, C3-C8 cycloalkyl group (which may be substituted by a substituent selected from C1-C6 alkyl or C1-C6 haloalkyl group), C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 alkyl group, C1-C6 alkoxy group, C1-C6 alkyl carbonyl amino group (which may be selected from the substituent group) c (substituents in the group), C1~C6 alkyl carbonyl, C1~C6 alkoxy carbonyl, amino carbonyl, C1~C6 alkylamino carbonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl (the aryl group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (substituents in the group), substitution of one or more substituents in the cyano group), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, C1-C6 alkylamino groups (the amino group can be selected from the substituent group group) c (substituents in the group), one or more substituents in the cyano group), or a 3-6 membered heterocyclic group (the heterocyclic group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (substituent substitution in the group), (substituent substitution of one or more substituents in the cyano group), Substitute basis set cThis indicates C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl (which may be substituted by a substituent selected from C1-C6 alkyl or C1-C6 haloalkyl), C1-C6 alkoxyC1-C6 alkyl, C1-C6 haloalkyloxyC1-C6 alkyl, cyanoC1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl or C1-C6 alkoxycarbonyl).

[0010] (2) Nicotinamide derivatives or their salts represented by general formula [I]. [Chemistry 2] [In the formula, Q indicates -NR a R b Or nitro, W represents an oxygen atom or a sulfur atom. Y represents an oxygen atom or a sulfur atom (the sulfur atom can be oxidized by one or two oxygen atoms). A 1 This represents an oxygen atom, a sulfur atom (which can be oxidized by one or two oxygen atoms), -CH2-, or -NR. c , A 2 Represents -CH- or nitrogen atom, R 1 This represents hydrogen atoms, halogen atoms, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl or C1~C6 alkoxy groups, R 2 and R 3 Each of these elements independently represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylthio, C1-C6 alkyl, C1-C6 alkylsulfinyl, C1-C6 alkyl, C1-C6 alkylsulfonyl, C1-C6 alkyl, C1-C6 alkylamino (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group)α (substituent with one or more substituents), C1-C6 alkoxy, cyano, formyl, carboxyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, amino carbonyl, C1-C6 alkylamino carbonyl (the amino group can be selected from the substituent group) c Substituents in the group), C3~C8 cycloalkylaminocarbonyl (the cycloalkyl group can be selected from the substituent group) β The amino group can be substituted with a substituent selected from the group consisting of substituents. c Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (more than one substituent in R), further, R 2 With R 3 They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u The 0 to 1 atoms or groups of atoms in the ring together form a 5 to 6-membered ring, which can be replaced by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 alkoxy, or oxo groups. R 4 This represents a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group include C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, formyl, C1-C6 alkyl carbonyl, or C1-C6 alkoxy carbonyl. L represents L-1, L-2, or L-3. R 5 This represents a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarbonyl, C6-C6 alkylyl, C6-C6 alkylyl, C2-C6 alkylyl ... 12 aryl (which can be selected from the substituent group) α (one or more substituents in the group), cyano C1~C6 alkyl or C6~C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (with one or more substituents in the group) R 6This represents hydrogen atoms, halogen atoms, hydroxyl groups, cyano groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, methoxy or C3~C6 alkoxy, R 7 This represents hydrogen atoms, halogen atoms, hydroxyl groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) R 8 Indicates hydroxyl, mercapto, cyano, -CR d R e R f -OR h -NR i R k C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group) β Substituents in the group (C3-C8 cycloalkenyl, C2-C6 alkenyl, C2-C6 ynyl, tris(C1-C6 alkyl)silylC2-C6 ynyl, C3-C8 cycloalkylC2-C6 ynyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C1~C6 alkylthio, C1~C6 alkylsulfinyl, C1~C6 alkylsulfonyl, C3~C8 cycloalkylthio (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl group (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C3~C8 cycloalkylsulfonyl groups (the cycloalkyl group can be selected from the substituent group) β Substituents in the group (e.g., C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkoxy-C1-C6 alkylthio, C1-C6 alkoxy-C1-C6 alkylsulfinyl, C1-C6 alkoxy-C1-C6 alkylsulfonyl, cyanothio, C1-C6 alkylcarbonylthio, aminosulfonyl, C1-C6 alkylaminosulfonyl (the amino group can be selected from the substituent group)). c Substituents in (C6~C) 12arylthio (the aryl group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfinyl (the aryl group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfonyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylthio groups (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylsulfinyl group (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylsulfonyl groups (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3- to 6-membered heterocyclic thio groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic sulfinyl group (this heterocyclic group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic sulfonyl group (this heterocyclic group can be selected from the substituent group) α (substituents of one or more substituents), formyl group, carboxyl group, C1-C6 alkyl carbonyl group, C3-C8 cycloalkyl carbonyl group (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C1~C6 alkoxy-C1~C6 alkyl carbonyl, C1~C6 alkoxy carbonyl, amino carbonyl, C3~C8 cycloalkyl amino carbonyl (the cycloalkyl group can be selected from the substituent group) β The amino group can be substituted with a substituent selected from the group consisting of substituents. c Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (substituents of one or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (substitution of one or more substituents), -C (=NR) m )R n base or -C(R) o )=CR p (R s )base, R 9 This represents hydrogen atoms, halogen atoms, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which can be selected from the substituent group) α (substituent with one or more substituents) or 5-12 heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (with one or more substituents in the group) R x and R y Each independently represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group; further, R x and R y They can form oxygen groups together. R z Indicates hydrogen atom, halogen atom, or C1~C6 alkyl group. R a This represents hydrogen atoms, hydroxyl groups, amino groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, C1-C6 alkylamino (the amino group can be selected from the substituent group) c Substituents in the group include: formyl group, C1-C6 alkyl carbonyl group, C1-C6 haloalkyl carbonyl group, C1-C6 alkoxy C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, amino carbonyl group, and C1-C6 alkylamino carbonyl group (the amino group can be selected from the substituent group group). c Substituents in the group), 3-6 membered heterocyclic groups (the heterocyclic group can be selected from the substituent group group) α (with one or more substituents in the group) R b Represents a hydrogen atom. In addition, R a and R b They can together form (=CH)-C1~C6 alkyl groups, (=CH)-C6~C 12 aryl (which can be selected from the substituent group) α (substituents of one or more groups) or =CH-N(C1~C6 alkyl)2, Rc Represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 alkyl carbonyl group. R d R e Each of these groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in (e.g., C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy or tris(C1-C6 alkyl)silyloxy), or R d and R e They can form =CH2 together, and further, R d With R e They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u The 0 to 2 atoms or groups together form a 3 to 6-membered ring, which can be replaced by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 haloalkyl, C1 to C6 alkoxy, or oxo groups. R f This indicates chlorine, bromine, iodine, hydroxyl, mercapto, amino, cyano, nitro, C1-C6 alkyl, and C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 ynyl, C3~C8 cycloalkyl, C2~C6 ynyl (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C8 cycloalkyloxy C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C6-C6 alkyl) 12 aryloxy C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic oxy-C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryloxy C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (One or more substituents), mercapto C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C3-C8 cycloalkylthio C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group)β (substituents in the group), C3~C8 cycloalkyl sulfinyl C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 haloalkylthio-C1-C6 alkyl, C1-C6 haloalkylsulfinyl-C1-C6 alkyl, C1-C6 haloalkylsulfonyl-C1-C6 alkyl, C1-C6 alkylaminosulfonyl-C1-C6 alkyl (the amino group can be selected from the substituent group)). c Substituents in (e.g., cyanothio C1-C6 alkyl, amino C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl (the amino group can be selected from the substituent group)). c (substituents in the group), C3~C8 cycloalkylamino C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β The amino group can be substituted with a substituent selected from the group consisting of substituents. c Substituents in (C1-C6 alkyl halogenated amino groups) (the amino group can be selected from the substituent group) c (substituents in the group), C1~C6 alkyl carbonyl amino C1~C6 alkyl (the amino group can be selected from the substituent group) c (substituents in the group), C1~C6 alkoxycarbonyl amino C1~C6 alkyl (the amino group can be selected from the substituent group) c (substituents in the group), C1~C6 alkylsulfonylamino C1~C6 alkyl (the amino group can be selected from the substituent group) c Substituents in (C1-C6 haloalkylsulfonylamino C1-C6 alkyl (the amino group can be selected from the substituent group) c Substituents in (e.g., aminosulfonylamino C1-C6 alkyl, where the amino group can be selected from the substituent group) c (substituents in the group), C1~C6 alkylaminosulfonylaminoC1~C6 alkyl (the amino group can be selected from the substituent group) c Substituents in the group (e.g., cyano C1-C6 alkyl, formyl C1-C6 alkyl, carboxyl C1-C6 alkyl, C1-C6 alkyl carbonyl C1-C6 alkyl, C1-C6 alkoxy carbonyl C1-C6 alkyl, amino carbonyl C1-C6 alkyl, C1-C6 alkyl amino carbonyl C1-C6 alkyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 arylaminocarbonyl C1~C6 alkyl (the aryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. cSubstituents in (e.g., hydroxyaminocarbonyl C1-C6 alkyl, C1-C6 alkoxyaminocarbonyl C1-C6 alkyl) (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 Aryl carbonyl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylcarbonyl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3-6 membered heterocyclic carbonyl C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (substituent with one or more substituents), aminothiocarbonyl C1-C6 alkyl, C1-C6 alkylaminothiocarbonyl C1-C6 alkyl (the amino group can be selected from the substituent group) c Substituents in (C1~C6 alkyl)-C (=NR) m )R n C6~C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, C3-C8 cycloalkyloxy (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C1-C6 haloalkyloxy groups, C3-C8 cycloalkyl groups, and C1-C6 alkoxy groups (the cycloalkyl group can be selected from the substituent group). β (substituents in C1-C6 alkoxy groups, C1-C6 alkoxy groups, C6-C6 alkoxy groups) 12 Aryl C1~C6 alkoxy (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkoxy groups (the heteroaryl group can be selected from the substituent group) α (One or more substituents in the group), 3-6 membered heterocyclic C1-C6 alkoxy groups (the heterocyclic group can be selected from the substituent group group) α (one or more substituents), C1-C6 alkyl carbonyloxy group, C3-C8 cycloalkyl carbonyloxy group (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), aminocarbonyloxy group, C6~C 12 aryloxy group (the aryl group can be selected from the substituent group) α(one or more substituents in the group), 5-12 membered heteroaryloxy groups (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic oxygen groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylthio (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl group (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C3~C8 cycloalkylsulfonyl groups (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C1~C6 haloalkylthio, C1~C6 haloalkylsulfinyl, C1~C6 haloalkylsulfonyl, C3~C8 cycloalkyl C1~C6 alkylthio (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl C1~C6 alkylsulfinyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C3-C8 cycloalkyl C1-C6 alkylsulfonyl group) (the cycloalkyl group can be selected from the substituent group) β (Substituents in the group), C1~C6 alkoxy-C1~C6 alkylthio, C1~C6 alkoxy-C1~C6 alkylsulfinyl, C1~C6 alkoxy-C1~C6 alkylsulfonyl, cyanothio, C1~C6 alkylcarbonylthio, aminosulfonyl, C1~C6 alkylaminosulfonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 arylthio (the aryl group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfinyl (the aryl group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfonyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylthio groups (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylsulfinyl group (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylsulfonyl groups (the heteroaryl group can be selected from the substituent group) α (one or more substituents in the group), C1-C6 alkylamino (the amino group can be selected from the substituent group) cSubstituents in (C3-C8 cycloalkylamino groups, where the cycloalkyl group can be selected from the substituent group) β The amino group can be substituted with a substituent selected from the group consisting of substituents. c Substituents in (C1-C6 haloalkylamino groups, where the amino group can be selected from the substituent group) c Substituents in (substituents), aminocarbonylamino (the amino group can be selected from the substituent group) c Substituents in (C1-C6 alkylamino carbonylamino groups) (the amino group can be selected from the substituent group) c Substituents in (C1-C6 alkoxycarbonyl amino groups, which can be selected from the substituent group) α Substituents in (C1-C6 alkylsulfonylamino groups, where the amino group can be selected from the substituent group) c Substituents in (C1-C6 haloalkylsulfonylamino groups, where the amino group can be selected from the substituent group group) c (substituents in the group), aminosulfonylamino (the amino group can be selected from the substituent group) c Substituents in (C1-C6 alkylaminosulfonylamino groups, where the amino group can be selected from the substituent group) c Substituents in the group), 5-12 membered heteroarylamino groups (the heteroaryl group can be selected from the substituent group group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in the group include: formyl group, carboxyl group, C1-C6 alkyl carbonyl group, and C3-C8 cycloalkyl carbonyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkoxy-C1-C6 alkyl-carbonyl, C1-C6 alkoxy-carbonyl, C6-C6) 12 aryloxycarbonyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryloxycarbonyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), amino carbonyl, C1-C6 alkylamino carbonyl (the amino group can be selected from the substituent group) c Substituents in (e.g., hydroxyaminocarbonyl, C1-C6 alkoxyaminocarbonyl, where the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in the group), 5-12 membered heteroarylaminocarbonyl (the heteroaryl group can be selected from the substituent group) αThe amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in the group), 3-6 membered heterocyclic amino carbonyl groups (the heterocyclic group can be selected from the substituent group group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in (e.g., aminothiocarbonyl, C1-C6 alkylaminothiocarbonyl, where the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl carbonyl (the aryl group can be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylcarbonyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3- to 6-membered heterocyclic carbonyl groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (substituents of one or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents in) or -C (=NR) m )R n base, R h This represents a hydrogen atom, a C2-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C8 cycloalkyloxy C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C6-C6 alkyl) 12 aryloxy C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryloxy C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic oxy-C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α(One or more substituents), mercapto C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C3-C8 cycloalkylthio C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl C1~C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 haloalkylthio-C1-C6 alkyl, C1-C6 haloalkylsulfinyl-C1-C6 alkyl, C1-C6 haloalkylsulfonyl-C1-C6 alkyl, C6-C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylaminosulfonyl (the amino group can be selected from the substituent group) c (substituents in the group), formyl group, C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, amino carbonyl group, C1-C6 alkylamino carbonyl group (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group can be selected from the substituent group) α The amino group can be substituted by one or more substituents, and the amino group can be selected from the group consisting of substituents. c Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (substituents of one or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (substituents of one or more substituents), -N=CH-(C1~C6 alkyl) or -N=C(C1~C6 alkyl)2, R i This represents a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). βSubstituents in (e.g., cyano C1-C6 alkyl, C6-C6 alkyl) 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents) or 3- to 6-membered heterocyclic C1- to C6 alkyl groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) R k This represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C8 cycloalkyloxy C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C1-C6 alkylthiolated C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, cyano C1-C6 alkyl, C6-C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group can be selected from the substituent group) α (one or more substituents), C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl (the amino group can be selected from the substituent group) c Substituents in the group (e.g., formyl group, C1-C6 alkyl carbonyl group, C3-C8 cycloalkyl carbonyl group, where the cycloalkyl group can be selected from the substituent group group) β Substituents in (C1-C6 haloalkyl carbonyl, C1-C6 alkoxy C1-C6 alkyl carbonyl, cyano C1-C6 alkyl carbonyl, C6-C6 alkyl carbonyl) 12 Aryl C1~C6 alkyl carbonyl (the aryl group can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl carbonyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3-6 membered heterocyclic C1-C6 alkyl carbonyl (this heterocyclic group can be selected from the substituent group) α(one or more substituents), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl carbonyl (the aryl group can be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylcarbonyl (the heteroaryl group can be selected from the substituent group) α (substituent with one or more substituents), 3- to 6-membered heterocyclic carbonyl groups (the heterocyclic group can be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) Furthermore, R i With R k They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u The 0 to 1 atoms or groups of atoms in the ring together form a nitrogen-containing 4 to 6-membered ring, which can be selected from halogen atoms, C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 alkyl carbonyl, C1 to C6 alkoxy carbonyl, amino carbonyl, and C1 to C6 alkyl amino carbonyl (the amino group can be selected from the substituent group). c Substituents in (C1-C6 alkyl carbonyl amino groups, where the amino group can be selected from the substituent group) c (Substituent substitution in the group) or more than one chemically acceptable substituent substitution in the oxo group. R m This indicates hydroxyl, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, and C3-C8 cycloalkyloxy (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 alkyloxy groups, C1-C6 alkylamino groups, where the amino group can be selected from the substituent group group) c (substituents in the group) or C1~C6 alkyl carbonyl amino (the amino group can be selected from the substituent group) c (substituents in the text) R n This represents hydrogen atoms, halogen atoms, cyano groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). βSubstituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) R o This indicates cyano, C1-C6 alkyl, or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarbonyl, C3-C8 cycloalkylcarbonyl (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl (the amino group can be selected from the substituent group)). c Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in the group) R p This represents a hydrogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1~C6 haloalkyl, C1~C6 alkoxy, C1~C6 alkyl, C1~C6 alkoxy, C1~C6 alkyl carbonyl, C3~C8 cycloalkyl carbonyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C1~C6 alkoxycarbonyl or C1~C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c (substituents in the text) R s This indicates cyano, C1-C6 alkyl, or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1~C6 haloalkyl, C1~C6 alkoxy, C1~C6 alkyl, C1~C6 alkoxy, C1~C6 alkyl carbonyl, C3~C8 cycloalkyl carbonyl (the cycloalkyl group can be selected from the substituent group) β(substituents in the group), C1~C6 alkoxycarbonyl or C1~C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c (substituents in the text) Furthermore, R p With R s They can bond with each other to form a 5-6 membered ring with 0-2 atoms or groups selected from carbon, oxygen, and sulfur (which can be oxidized by one or two oxygen atoms). This 5-6 membered ring can be substituted by one or more chemically acceptable substituents selected from C1-C6 alkyl, C1-C6 alkoxy, or oxo groups. R u Indicates a hydrogen atom or a C1-C6 alkyl group. Substitute basis set α This indicates halogen atoms, hydroxyl groups, mercapto groups, amino groups, cyano groups, nitro groups, C1-C6 alkyl groups, C1-C6 haloalkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C3~C8 halocycloalkyl groups (the halocycloalkyl group can be selected from the substituent group) β Substituents in the group (C1-C6 alkoxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C8 cycloalkyl, C2-C6 ynyl (the cycloalkyl group can be selected from the substituent group)). β Substituents in the group), C1-C6 alkoxy groups, C3-C8 cycloalkyloxy groups (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl oxy, C1-C6 alkoxy, C6-C6 alkoxy) 12 aryl C1-C6 alkoxy (the aryl group may be substituted by one or more substituents selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, cyano), C2-C6 alkenoxy, C2-C6 alkynoxy, tris(C1-C6 alkyl)silyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino (the amino group may be selected from the substituent group) c Substituents in (C1-C6 alkyl carbonyl amino groups, where the amino group can be selected from the substituent group) c Substituents in the group), C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group can be selected from the substituent group) β Substituents in the group), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C)12 aryl (the aryl group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (substituents in the group), substitution of one or more substituents in the cyano group), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, C1-C6 alkylamino groups (the amino group can be selected from the substituent group group) c Substituents in the group), substitution of one or more substituents in the cyano group), oxo group or -C (=NR) m )R n base, Substitute basis set β This indicates a halogen atom, hydroxyl group, amino group, cyano group, C1-C6 alkyl group, C3-C8 cycloalkyl group (which may be substituted by a substituent selected from C1-C6 alkyl or C1-C6 haloalkyl group), C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 alkyl group, C1-C6 alkoxy group, C1-C6 alkyl carbonyl amino group (which may be selected from the substituent group) c (substituents in the group), C1~C6 alkyl carbonyl, C1~C6 alkoxy carbonyl, amino carbonyl, C1~C6 alkylamino carbonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl (the aryl group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (substituents in the group), substitution of one or more substituents in the cyano group), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, C1-C6 alkylamino groups (the amino group can be selected from the substituent group group) c (substituents in the group), one or more substituents in the cyano group), or a 3-6 membered heterocyclic group (the heterocyclic group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (substituent substitution in the group), (substituent substitution of one or more substituents in the cyano group), Substitute basis set cThis indicates C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl (which may be substituted by a substituent selected from C1-C6 alkyl or C1-C6 haloalkyl), C1-C6 alkoxyC1-C6 alkyl, C1-C6 haloalkyloxyC1-C6 alkyl, cyanoC1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl or C1-C6 alkoxycarbonyl).

[0011] (3) An agricultural and horticultural plant disease control agent, characterized in that it contains the nicotinamide derivative or its salt described in (2) above as an active ingredient.

[0012] (4) The agricultural and horticultural plant disease control agent according to (1) or (3) above, wherein the plant disease originates from pathogens.

[0013] (5) The plant disease control agent for agricultural and horticultural use described in (4) above, wherein the plant disease is classified as any one of the following: fungi (basidiomycetes, ascomycetes, mucormycetes, etc.), stridermatiformes (oomycetes, etc.), foraminifera (filamentous worms, etc.), and bacteria.

[0014] (6) The agricultural and horticultural plant disease control agent described in (4) above, wherein the plant disease is classified as a tegumentous organism (such as an oomycete).

[0015] (7) An agricultural and horticultural plant disease control agent comprising the nicotinamide derivative or salt thereof described in (2) above, and a pesticide-acceptable carrier.

[0016] (8) A method for controlling plant diseases, wherein an effective amount of the nicotinamide derivative or salt thereof described in (2) above is used to control plant diseases by means of dispersal, soil application, surface application, seed treatment, soaking, poison bait or fumigation.

[0017] (9) The method described in (8) above is used to disperse useful plants or a portion of useful plants or the place where the useful plants grow, or to treat the seeds of useful plants.

[0018] (10) The method according to (8) above, wherein the plant disease originates from pathogenic fungi.

[0019] (11) The method according to (9) above, wherein the plant disease originates from pathogenic fungi.

[0020] (12) According to the method described in (10) above, the plant disease is classified into any one of the following: fungi (basidiomycetes, ascomycetes, mucormycetes, etc.), tegumentosa (oomycetes, etc.), foraminifera (filamentosa, etc.) and bacteria.

[0021] (13) According to the method described in (11) above, the plant disease is classified into any one of the following: fungi (basidiomycetes, ascomycetes, mucormycetes, etc.), tegumentosa (oomycetes, etc.), foraminifera (filopods, etc.) and bacteria.

[0022] (14) According to the method described in (10) above, wherein the plant disease is classified into the kingdom Oomycetes (such as the class Oomycetes).

[0023] (15) According to the method described in (11) above, wherein the plant disease is classified into the kingdom of tegumentosa (such as Oomycetes).

[0024] (16) The use of the nicotinamide derivatives or their salts described in (2) above as agricultural and horticultural plant disease control agents for useful plants.

[0025] Invention Effects The compounds of the present invention, namely nicotinamide derivatives or their salts, are useful as active ingredients in pesticides such as agricultural and horticultural plant disease control agents.

[0026] Agricultural and horticultural plant disease control agents containing the compounds of the present invention exhibit excellent control effects on a wide range of plant diseases caused by fungi (basidiomycetes, ascomycetes, mucormycetes, etc.), tegumentosa (oomycetes, etc.), foraminifera (filamentosa, etc.), and bacteria. In addition, they can also control fungi that have acquired resistance.

[0027] The method for controlling plant diseases of the present invention, by distributing an effective amount of the nicotinamide derivative of the present invention or its salt to a useful plant or a part thereof or the place where the plant grows, exhibits excellent control effects on a wide range of plant diseases. In addition, it can also control fungi that have acquired resistance.

[0028] According to the use of the nicotinamide derivative or salt thereof of the present invention, the nicotinamide derivative or salt thereof is effective as an agricultural and horticultural plant disease control agent for useful plants, thereby achieving excellent control effects against a wide range of plant diseases, and is also able to control fungi that have acquired resistance. Detailed Implementation

[0029] The symbols and terms used in this instruction manual are explained.

[0030] In this invention, "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0031] In this invention, expressions such as "C1~C6" indicate that the number of carbons of the subsequent substituents is 1~6 in this case.

[0032] In this invention, unless otherwise specified, "C1~C6 alkyl" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, such as 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, 3,3-dimethyl-1-butyl, etc.

[0033] In this invention, unless otherwise specified, "C1-C6 haloalkyl" refers to a straight-chain or branched haloalkyl group with 1-6 carbon atoms substituted by the same or different 1-13 halogen atoms. Examples include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, iodomethyl, dichlorofluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 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, etc. 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-Difluoropropyl, 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 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-Dichloropropyl 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-Hepenofluorobutyl, 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-Trifluoro-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, 1-Iodobutyl, 2-Iodobutyl, 3-Iodobutyl, 4-Iodobutyl, 4-Chloro-1,1,2,2,3,3,4,4-Obafluorobutyl, 4-Bromo-1,1,2,2,3,3,4,4-Obafluorobutyl, 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, undecylfluoropentyl, 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, undecylchloropentyl, 1-bromopentyl, 2-bromopentyl, 3-bromopentyl, 4-bromopentyl, 5-bromopentyl, 5-iodopentyl, 1-fluorohexyl, 2-fluorohexyl, 3-fluorohexyl, 4-fluorohexyl 5-Fluorohxyl, 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-undecanofluorohexyl, tridecanofluorohexyl, 1-chlorohexyl, 2-chlorohexyl, 3-chlorohexyl, 4-chlorohexyl, 5-chlorohexyl, 6-chlorohexyl, 5-bromohexyl, 6-bromohexyl, 5-iodohexyl, or 6-iodohexyl, etc.

[0034] In this invention, unless otherwise specified, "C3~C8 cycloalkyl" refers to a cycloalkyl group with 3 to 8 carbon atoms, and the ring can be arbitrarily substituted by the alkyl group within the specified range of carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl groups.

[0035] In this invention, unless otherwise specified, "C3~C8 halocycloalkyl" refers to a cycloalkyl group with 3 to 8 carbon atoms that is replaced by the same or different 1 to 11 halogen atoms, and the ring can be arbitrarily replaced by alkyl or haloalkyl groups within the specified range of carbon atoms. Examples include 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, and 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, 4,4-difluorocyclohexyl, 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 or 4,4-diiodocyclohexyl groups, etc.

[0036] In this invention, unless otherwise specified, "C2~C6 alkenyl" refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, such as 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-pentene -3-yl, 2-pentenyl, 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-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, etc.

[0037] In this invention, unless otherwise specified, "C3~C8 cycloalkenyl" refers to a cycloalkenyl group with 3 to 6 carbon atoms, such as 1-cyclopropen-1-yl, 1-cyclobuten-1-yl, 1-cyclopenten-1-yl, 1-cyclohexen-1-yl, 1-cyclohepten-1-yl or 1-cycloocten-1-yl.

[0038] In this invention, unless otherwise specified, "C2~C6 ynyl" refers to a straight-chain or branched ynyl group with 2 to 6 carbon atoms, such as 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-propyl)-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, or 2,2-dimethyl-3-butynyl, etc.

[0039] In this invention, unless otherwise specified, "C1~C6 alkoxy" means that the alkyl part is (C1~C6 alkyl)-O- group as described above, such as 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, or n-hexyloxy, etc.

[0040] In this invention, unless otherwise specified, "C3~C8 cycloalkyloxy" means that the cycloalkyl part is (C3~C8 cycloalkyl)-O- group as described above, such as cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, or cyclooctoxy.

[0041] In this invention, unless otherwise specified, "C1~C6 haloalkyloxy" means that the haloalkyl portion is (C1~C6 haloalkyl)-O- group as described above. Examples 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, 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, 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-Hepenofluorobutoxy, 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-bis(trifluoromethyl)propoxy, 2,2,3,3,4,4,5,5,6,6,6-undecanofluorohexyloxy, 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)butoxy, or perfluorohexyloxy, etc.

[0042] In this invention, unless otherwise specified, "C2~C6 alkenoxy" means that the alkenyl part is (C2~C6 alkenyl)-O-yl as described above, such as ethoxy, 1-propenoxy, isopropenoxy, 2-propenoxy, 1-methyl-2-propenoxy, 2-methyl-2-propenoxy, 2-butenoxy, 3-butenoxy, 3-methyl-2-butenoxy, 2-methyl-2-butenoxy, 2-pentenoxy, 3-pentenoxy, 4-pentenoxy, 2-hexenoxy, 3-hexenoxy, 4-hexenoxy, or 5-hexenoxy.

[0043] In this invention, unless otherwise specified, "C2~C6 alkynoxy" means that the alkynyl group is (C2~C6 alkynyl)-O- group as described above, such as acetylenoxy, 1-propynoxy, 2-propynoxy, 1-methyl-2-propynoxy, 1-ethyl-2-propynoxy, 1-butynoxy, 2-butynoxy, 3-butynoxy, 1-methyl-2-butynoxy, 1-pentynoxy, 2-pentynoxy, 3-pentynoxy, 4-pentynoxy, or 4,4-dimethyl-2-pentynoxy.

[0044] In this invention, unless otherwise specified, "tri(C1~C6 alkyl)silyloxy" means that the alkyl part is (C1~C6 alkyl)3-Si-O-yl as described above. The three alkyl groups can be the same or different from each other. Examples include trimethylsilyloxy, triethylsilyloxy, triisopropylsilyloxy, dimethylisopropylsilyloxy, or tert-butyldimethylsilyloxy.

[0045] In this invention, unless otherwise specified, "C6~C" 12"Aryl" refers to an aryl group having 6 to 12 carbon atoms, such as phenyl, 2-biphenyl, 4-biphenyl, naphth-1-yl, or naphth-2-yl groups.

[0046] In this invention, unless otherwise specified, "5-12 membered heteroaryl" refers to a monocyclic or fused bicyclic aromatic heterocycle containing one or more heteroatoms selected from nitrogen, oxygen, and sulfur atoms, in addition to a carbon atom. Examples of monocyclic aromatic heterocycles 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-tri ... 3-Triazine-5-yl, 1,2,4-Triazine-3-yl, 1,2,4-Triazine-5-yl, 1,2,4-Triazine-6-yl, 1,3,5-Triazine, Thiophene-2-yl, Thiophene-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, Isothiazol-5-yl, Oxazol-2-yl, Oxazol -4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, imidazole-2-yl, imidazole-4-yl, imidazole-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 -thiadiazole-3-yl, 1,2,4-thiadiazole-5-yl, 1,2,5-thiadiazole-3-yl, 1,3,4-oxadiazole-2-yl, 1,2,3-oxadiazole-4-yl, 1,2,3-oxadiazole-5-yl, 1,2,4-oxadiazole-3-yl, 1,2,4-oxadiazole-5-yl, 1,2,5-oxadiazole-3-yl or 1,3,5-triazin-2-yl, etc., as fused bicyclic heterocycles, are formed by reacting one of the monocyclic groups with a benzene ring or with any of the heteroaromatic monocyclic groups to form a C8~C3 ring. 10Fused bicyclic moieties formed by the fusion of bicyclic groups include, for example, indole-1-yl, indole-2-yl, indole-3-yl, indole-4-yl, indole-5-yl, indole-6-yl, indole-7-yl, benzimidazole-1-yl, benzimidazole-2-yl, benzimidazole-4-yl, benzimidazole-5-yl, benzimidazole-6-yl, benzimidazole-7-yl, indazole-1-yl, indazole-3-yl, indazole-4-yl, indazole-5-yl, indazole-6-yl, indazole-7-yl, benzotriazole-1-yl, benzotriazole-4-yl, benzotriazole-5-yl, benzotriazole-6-yl, benzotriazole-7-yl, isoquinoline-1-yl, isoquinoline-1-yl, isoquinoline-2-yl, benzimidazole-4-yl, benzotriazole-5-yl, benzotriazole-6-yl, benzotriazole-7-yl, isoquinoline-1-yl, isoquinoline-2-yl, isoquinoline-2-yl, isoquinoline-3-yl, isoquinoline-4-yl, isoquinoline-5-yl, isoquinoline-6-yl, isoquinoline ...2-yl, isoquinoline-2-yl, isoquino Quinoline-3-yl, isoquinoline-4-yl, isoquinoline-5-yl, isoquinoline-6-yl, isoquinoline-7-yl, isoquinoline-8-yl, quinoline-2-yl, quinoline-3-yl, quinoline-4-yl, quinoline-5-yl, quinoline-6-yl, quinoline-7-yl, quinoline-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, benzothiophene-2-yl, benzothiophene-3-yl, benzothiophene-4-yl, benzothiophene-5-yl, benzothiophene Thiophene-6-yl, benzothiophene-7-yl, benzoisoxazole-3-yl, benzoisoxazole-4-yl, benzoisoxazole-5-yl, benzoisoxazole-6-yl, benzoisoxazole-7-yl, pyrazolopyridin-1-yl, pyrazolopyridin-3-yl, pyrazolopyridin-4-yl, pyrazolopyridin-5-yl, pyrazolopyridin-6-yl, pyrazolopyrimidine-1-yl, pyrazolopyrimidine-2-yl, pyrazolopyrimidine-3-yl, pyrazolopyrimidine-5-yl, pyrazolopyrimidine-6-yl, pyrazolopyrimidine-7-yl, pyrrolopyridin-1-yl, pyrrolopyridin-2-yl, pyrrolopyridin-3-yl, pyrrolopyridin-4-yl, pyrrolopyridin-5-yl, pyrrolopyridin-6-yl - , triazolidine-3-yl, triazolidine-4-yl, triazolidine-5-yl, triazolidine-6-yl, triazolidine-7-yl, triazolidine-2-yl, triazolidine-3-yl, triazolidine-6-yl, triazolidine-7-yl, quinazoline-2-yl, quinazoline-4-yl, quinazoline-5-yl, quinazoline-6-yl, quinazoline-7-yl, quinazoline-8-yl, quinoxaline-2-yl, quinoxaline-3-yl, quinoxaline-5-yl, quinoxaline-6-yl, quinoxaline-7-yl, quinoxaline-8-yl, cinaline-3-yl, cinaline-4-yl, cinaline-5-yl, cinaline-6-yl, cinaline-7-yl, or cinaline-8-yl, etc.

[0047] In this invention, unless otherwise specified, "3- to 6-membered heterocyclic group" means that, in addition to a carbon atom, it contains one or more 3- to 6-membered non-aromatic heterocycles selected from oxygen, nitrogen, sulfur, and boron atoms. Examples include azircyclopropane-1-yl, azircyclopropane-2-yl, ethylene oxide-2-yl, oxetane-2-yl, oxetane-3-yl, thiobutane-2-yl, thiobutane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, azircyclobutane-1-yl, azircyclobutane-2-yl, azircyclobutane-3-yl, pyrrolidine-1-yl, and pyrrolidine-2-yl. Pyrrolidine-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperazine-1-yl, piperazine-2-yl, 4,5-dihydroisoxazole-3-yl, 1,3,2-dioxaborolane-2-yl, 1,3-dioxolane-2-yl, 1,3-dioxane-2-yl, 5-oxo-4,5-dihydro-1,2,4-oxadiazole-2-yl, 5-oxo-4,5-dihydro-1,2,4-thiadiazole-2-yl, 5-oxo-4,5-dihydro-1,3,4-oxadiazole-2-yl, 5-oxo-4,5-dihydro-1,3,4-thiadiazole-2-yl, or morpholino-4-yl groups, etc.

[0048] In this invention, unless otherwise specified, "C3~C8 cycloalkyl C2~C6 ynyl" means that the cycloalkyl part and the ynyl part are (C3~C8 cycloalkyl)-(C2~C6 ynyl)- groups as described above, such as cyclopropylethynyl, cyclobutylethynyl, cyclopentylethynyl, cyclohexylethynyl, cyclooctylethynyl or 3-(cyclopropyl)-2-propynyl, etc.

[0049] In this invention, unless otherwise specified, "hydroxy C1~C6 alkyl" means that the alkyl part is (hydroxy)-(C1~C6 alkyl)- group as described above, such as hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 2-hydroxypropane-2-yl, 3-hydroxy-2-methylpropane-2-yl, 4-hydroxy-2-methylbutane-2-yl, 5-hydroxy-2-methylpentane-2-yl and other groups.

[0050] In this invention, unless otherwise specified, "mercapto-C1~C6 alkyl" means that the alkyl part is (mercapto)-(C1~C6 alkyl)- group as described above, such as mercaptomethyl, 1-mercaptoethyl, 2-mercaptoethyl, 2-mercaptopropane-2-yl, 3-mercapto-2-methylpropane-2-yl, 4-mercapto-2-methylbutane-2-yl, 5-mercapto-2-methylpentane-2-yl and other groups.

[0051] In this invention, unless otherwise specified, "cyanoC1~C6 alkyl" means that the alkyl part is (cyano)-(C1~C6 alkyl)- group as described above, such as cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 1-cyanopropyl, 3-cyanopropyl, 2-cyano-2-propyl, 1-cyanobutyl, 4-cyanobutyl, 5-cyanopentyl or 6-cyanohexyl groups.

[0052] In this invention, unless otherwise specified, "formyl C1~C6 alkyl" means that the alkyl part is (formyl)-(C1~C6 alkyl)- group as described above, such as formylmethyl, 1-formylethyl, 2-formylethyl, 1-formylpropyl, 3-formylpropyl, 2-formyl-2-propyl, 1-formylbutyl, 4-formylbutyl, 5-formylpentyl or 6-formylhexyl groups.

[0053] In this invention, unless otherwise specified, "carboxyl C1~C6 alkyl" means that the alkyl part is (carboxyl)-(C1~C6 alkyl)- group as described above, such as carboxylmethyl, 1-carboxylethyl, 2-carboxylethyl, 1-carboxylpropyl, 3-carboxylpropyl, 2-carboxyl-2-propyl, 1-carboxylbutyl, 4-carboxylbutyl, 5-carboxylpentyl or 6-carboxylhexyl, etc.

[0054] In this invention, unless otherwise specified, "aminoC1~C6 alkyl" means that the alkyl part is (amino)-(C1~C6 alkyl)- group as described above, such as aminomethyl, 1-aminoethyl, 2-aminoethyl, 1-aminopropyl, 3-aminopropyl, 2-amino-2-propyl, 1-aminobutyl, 4-aminobutyl, 5-aminopentyl or 6-aminohexyl, etc.

[0055] In this invention, unless otherwise specified, "cyanothioC1~C6 alkyl" means that the alkyl part is (cyanothio)-(C1~C6 alkyl)-yl as described above, such as 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 or 6-(cyanothio)hexyl, etc.

[0056] In this invention, unless otherwise specified, "aminocarbonyl C1~C6 alkyl" means that the alkyl part is H2N-C(O)-(C1~C6 alkyl)- group as described above, such as carbamoylmethyl, 1-carbamoylethyl or 2-carbamoylethyl groups.

[0057] In this invention, unless otherwise specified, “C1~C6 alkylaminocarbonyl C1~C6 alkyl” means that the alkyl part is (C1~C6 alkyl)-NH-C(O)-(C1~C6 alkyl)- group as described above, such as N-methylcarbamoylmethyl, N-ethylcarbamoylmethyl or N-(tert-butyl)carbamoylmethyl groups.

[0058] In this invention, unless otherwise specified, "C1~C6 alkylaminosulfonylaminoC1~C6 alkyl" means that the alkyl part is (C1~C6 alkyl)-NH-S(O)2-NH-(C1~C6 alkyl)-yl, for example, [(N-methylaminosulfonyl)amino]methyl, [(N-ethylaminosulfonyl)amino]methyl, [(N-isopropylaminosulfonyl)amino]methyl, 1-[(N-methylaminosulfonyl)amino]ethyl or 2-[(N-methylaminosulfonyl)amino]ethyl, etc.

[0059] In this invention, unless otherwise specified, "hydroxyaminocarbonyl C1~C6 alkyl" means that the alkyl part is (hydroxy)-HN-C(O)-(C1~C6 alkyl)- group as described above, such as 2-(hydroxyamino)-2-oxoethyl or 3-(hydroxyamino)-3-oxopropyl groups.

[0060] In this invention, unless otherwise specified, "aminothiocarbonylC1~C6 alkyl" means that the alkyl part is H2N-C(S)-(C1~C6 alkyl)- group as described above, such as 2-amino-2-thiooxyethyl, 3-amino-3-thiooxypropyl or 1-amino-1-thiopropane-2-yl groups.

[0061] In this invention, unless otherwise specified, “C1~C6 alkylaminothiocarbonylC1~C6 alkyl” means that the alkyl part is (C1~C6 alkyl)-NH-C(S)-(C1~C6 alkyl)-yl, for example, 2-(methylamino)-2-thiooxyethyl, 2-(ethylamino)-2-thiooxyethyl or 1-(methylamino)-1-thiopropane-2-yl and other groups.

[0062] In this invention, unless otherwise specified, "tri(C1~C6 alkyl)silylC2~C6 ynyl" means that the alkyl part and the ynyl part are (C1~C6 alkyl)3-Si-(C2~C6 ynyl)-yl, for example, trimethylsilylethynyl, triethylsilylethynyl, triethylsilylethynyl, tert-butyldimethylsilylethynyl or 3-(trimethylsilyl)-2-propynyl and other groups.

[0063] In this invention, unless otherwise specified, "C1~C6 alkoxy-C1~C6 alkyl" means that the alkoxy moiety and the alkyl moiety are (C1~C6 alkoxy)-(C1~C6 alkyl)- groups as described above. Examples include methoxymethyl, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, tert-butoxymethyl, 1-methoxyethyl, 1-methoxy-1-methylethyl, 2-methoxyethyl, 1-ethoxyethyl, 2-ethoxyethyl, and 1-isopropoxyethyl. The group includes ethyl, 1-methoxypropyl, 2-methoxypropyl, 1-ethoxypropyl, 1-methoxybutyl, 1-ethoxybutyl, 3-methoxypropane-2-yl, 3-ethoxypropane-2-yl, 3-methoxy-2-methylpropane-2-yl, 3-ethoxy-2-methylpropane-2-yl, 4-methoxybutane-2-yl, 4-ethoxybutane-2-yl, 4-methoxy-2-methylbutane-2-yl, or 4-ethoxy-2-methylbutane-2-yl.

[0064] In this invention, unless otherwise specified, “C3~C8 cycloalkyloxyC1~C6 alkyl” means that the cycloalkyl part and the alkyl part are (C3~C8 cycloalkyl)-O-(C1~C6 alkyl)- groups as described above, such as cyclopropoxymethyl, cyclobutoxymethyl, cyclohexyloxymethyl, 1-cyclopropoxyethyl or 2-cyclopropoxyethyl groups.

[0065] In this invention, unless otherwise specified, "C1~C6 haloalkyloxy C1~C6 alkyl" means that the haloalkyloxy moiety and the alkyl moiety are (C1~C6 haloalkyloxy)-(C1~C6 alkyl)-yl as described above, such as 2-(difluoromethoxy)ethyl, 2-(trifluoromethoxy)ethyl, 2-(2,2-difluoroethoxy)ethyl, 2-(2,2,2-trifluoroethoxy)ethyl, 2-( Groups such as 3,3-difluoropropoxy)ethyl, 2-(3,3,3-trifluoropropoxy)ethyl, 3-(difluoromethoxy)propyl, 3-(trifluoromethoxy)propyl, 3-(2,2-difluoroethoxy)propyl, 3-(2,2,2-trifluoroethoxy)propyl, 3-(3,3-difluoropropoxy)propyl, 3-(3,3,3-trifluoropropoxy)propyl, 4-(trifluoromethoxy)butyl, or 5-(trifluoromethoxy)pentyl.

[0066] In this invention, unless otherwise specified, "C1~C6 alkoxy" means that the alkoxy moiety is (C1~C6 alkoxy)-(C1~C6 alkoxy)-, such as 2-methoxyethoxy, 3-methoxypropoxy, 2-ethoxyisopropoxy, 2-isopropoxybutoxy, 5-ethoxypentoxy, 6-ethoxyhexoxy, 2-(tert-butoxy)ethoxy, 2-methoxyisopentoxy, or 2-isopropoxyisobutoxy.

[0067] In this invention, unless otherwise specified, "C3~C8 cycloalkyl C1~C6 alkoxy" means that the cycloalkyl part and the alkoxy part are (C3~C8 cycloalkyl)-(C1~C6 alkoxy)- groups as described above, such as cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, 2-cyclopropylethoxy, 2-cyclobutylethoxy or 2-cyclopentylethoxy groups.

[0068] In this invention, unless otherwise specified, "C6~C" 12 "Aryl C1~C6 alkoxy" indicates that the aryl moiety and the alkoxy moiety are as described above (C6~C6). 12 Aryl)-(C1~C6 alkoxy)- group, for example, benzyloxy, 1-phenylethyloxy, 2-phenylethyloxy, 2-phenylpropyloxy, 2-phenylbutoxy, 1-phenylpentoxy, naphth-1-ylmethoxy or naphth-2-ylmethoxy groups.

[0069] In this invention, unless otherwise specified, "5-12-membered heteroaryl C1-C6 alkoxy" means that the heteroaryl moiety and the alkoxy moiety are (5-12-membered heteroaryl)-(C1-C6 alkoxy)- groups as described above. Examples include pyridinylmethoxy, pyrimidinylmethoxy, pyrazinylmethoxy, pyridazinylmethoxy, triazinylmethoxy, thiopheneylmethoxy, furanylmethoxy, pyrroleylmethoxy, pyrazolylmethoxy, thiazolylmethoxy, isothiazolylmethoxy, oxazolylmethoxy, isoxazolylmethoxy, imidazoleylmethoxy, and triazolylmethoxy. The groups include thiadiazole methoxy, oxadiazole methoxy, tetrazolyl methoxy, indolyl methoxy, benzimidazole methoxy, indazole methoxy, benzotriazole methoxy, isoquinolinyl methoxy, quinolinyl methoxy, benzothiazolyl methoxy, benzofuranyl methoxy, benzothiophenyl methoxy, benzoisooxazole methoxy, pyrazolopyridyl methoxy, pyrazolopyrimidinyl methoxy, pyrrolopyridyl methoxy, triazololopyridyl methoxy, triazololopyrimidinyl methoxy, quinazolinyl methoxy, quinoxolinyl methoxy, pyrolinyl methoxy, or pyridylethoxy.

[0070] In this invention, unless otherwise specified, "3-6 membered heterocyclic C1-C6 alkoxy" means that the heterocyclic group and the alkoxy group are (3-6 membered heterocyclic)-(C1-C6 alkoxy)- groups as described above. Examples include azircyclopropane methoxy, epoxy ethylene methoxy, oxacyclobutane methoxy, thiocyclobutane methoxy, tetrahydrofuranyl methoxy, tetrahydropyranyl methoxy, azircyclobutane methoxy, pyrrolidinyl methoxy, piperidinyl methoxy, piperazineyl methoxy, dihydroisooxazolyl methoxy, dioxaboryl methoxy, dioxopentaneyl methoxy, dioxinyl methoxy, morpholinyl methoxy, or azircyclopropane ethoxy, etc.

[0071] In this invention, unless otherwise specified, "C1~C6 alkyl carbonyl" means that the alkyl part is a (C1~C6 alkyl)-C(O)- group as described above, such as acetyl, propionyl, 2-methylpropionyl, 2,2-dimethylpropionyl, butyryl, 2-methylbutyryl, 3-methylbutyryl, 2-ethylbutyryl, 2,2-dimethylbutyryl, 2,3-dimethylbutyryl, 3,3-dimethylbutyryl, valeryl, 2-methylvaleryl, 3-methylvaleryl, 4-methylvaleryl or hexanoyl groups.

[0072] In this invention, unless otherwise specified, "C3~C8 cycloalkyl carbonyl" means that the cycloalkyl part is (C3~C8 cycloalkyl)-C(O)- group as described above, such as cyclopropane carbonyl, cyclobutane carbonyl, cyclopentane carbonyl, cyclohexane carbonyl, cycloheptane carbonyl or cyclooctane carbonyl groups.

[0073] In this invention, unless otherwise specified, "C1~C6 haloalkyl carbonyl" means that the haloalkyl part is (C1~C6 haloalkyl)-C(O)- group as described above, such as fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, trichloroacetyl, tribromoacetyl, 3,3,3-trifluoropropionyl, 3,3-difluoropropionyl or 4,4,4-trifluorobutyryl and other groups.

[0074] In this invention, unless otherwise specified, "C1~C6 alkoxycarbonyl" means that the alkoxy moiety is (C1~C6 alkoxy)-C(O)- group as described above. Examples 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, or 2,2-dimethylpropoxycarbonyl.

[0075] In this invention, unless otherwise specified, "cyanoC1~C6 alkyl carbonyl" means that the alkyl part is (cyano)-(C1~C6 alkyl)-C(O)- group as described above, such as 2-cyanoacetyl, 2-cyanopropionyl or 3-cyanopropionyl groups.

[0076] In this invention, unless otherwise specified, "C1~C6 alkyl carbonyloxy" means that the alkyl part is (C1~C6 alkyl)-C(O)-O- group as described above, such as methyl carbonyloxy, ethyl carbonyloxy, n-propyl carbonyloxy, isopropyl carbonyloxy, n-butyl carbonyloxy, isobutyl carbonyloxy, sec-butyl carbonyloxy, or tert-butyl carbonyloxy.

[0077] In this invention, unless otherwise specified, "C3~C8 cycloalkyl carbonyloxy" means that the cycloalkyl part is (C3~C8 cycloalkyl)-C(O)-O- group as described above, such as cyclopropyl carbonyloxy, cyclobutyl carbonyloxy, cyclopentyl carbonyloxy, cyclohexyl carbonyloxy, cycloheptyl carbonyloxy, or cyclooctyl carbonyloxy.

[0078] In this invention, unless otherwise specified, "C1~C6 alkyl carbonyl amino C1~C6 alkyl" means that the alkyl part is (C1~C6 alkyl)-C(O)-NH-(C1~C6 alkyl)-yl, and examples include 1-acetylamino-1-methylethyl, 1-propionylamino-1-methylethyl, 1-butyrylamino-1-methylethyl, 1-isobutyrylamino-1-methylethyl, 3-acetylamino-2-methylpropane-2-yl, 3-propionylamino-2-methylpropane-2-yl, 3-butyrylamino-2-methylpropane-2-yl, 3-isobutyrylamino-2-methylpropane-2-yl, etc.

[0079] In this invention, unless otherwise specified, “C1~C6 alkylthio” means that the alkyl part is (C1~C6 alkyl)-S-group as described above, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, or tert-butylthio.

[0080] In this invention, unless otherwise specified, "C1~C6 alkyl sulfinyl" means that the alkyl part is (C1~C6 alkyl)-S(O)- group as described above, such as methyl sulfinyl, ethyl sulfinyl, n-propyl sulfinyl, isopropyl sulfinyl, n-butyl sulfinyl, isobutyl sulfinyl, sec-butyl sulfinyl or tert-butyl sulfinyl groups.

[0081] In this invention, unless otherwise specified, "C1~C6 alkylsulfonyl" means that the alkyl part is (C1~C6 alkyl)-S(O)2- group as described above, such as methanesulfonyl, ethanesulfonyl, n-propanesulfonyl, isopropanesulfonyl, n-butanesulfonyl, isobutanesulfonyl, sec-butanesulfonyl or tert-butanesulfonyl groups.

[0082] In this invention, unless otherwise specified, "C3~C8 cycloalkylthio" means that the cycloalkyl part is a (C3~C8 cycloalkyl)-S-group as described above, such as cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cycloheptylthio, or cyclooctylthio.

[0083] In this invention, unless otherwise specified, "C3~C8 cycloalkyl sulfinyl" means that the cycloalkyl part is (C3~C8 cycloalkyl)-S(O)- group as described above, and examples include cyclopropyl sulfinyl, cyclobutyl sulfinyl, cyclopentyl sulfinyl, cyclohexyl sulfinyl, cycloheptyl sulfinyl or cyclooctyl sulfinyl groups.

[0084] In this invention, unless otherwise specified, "C3~C8 cycloalkylsulfonyl" means that the cycloalkyl part is (C3~C8 cycloalkyl)-S(O)2- group as described above, and examples include cyclopropanesulfonyl, cyclobutanesulfonyl, cyclopentanesulfonyl, cyclohexanesulfonyl, cycloheptanesulfonyl or cyclooctanesulfonyl groups.

[0085] In this invention, unless otherwise specified, "C1~C6 haloalkylthio" means that the haloalkyl part is a (C1~C6 haloalkyl)-S-group as described above. Examples 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, or 4,4,4-trifluorobutylthio.

[0086] In this invention, unless otherwise specified, "C1~C6 haloalkyl sulfinyl" means that the haloalkyl part is (C1~C6 haloalkyl)-S(O)- group as described above. Examples include fluoromethyl sulfinyl, difluoromethyl sulfinyl, trifluoromethyl sulfinyl, trichloromethyl sulfinyl, 2,2,2-trifluoroethyl sulfinyl, pentafluoroethyl sulfinyl, 2,2,2-trichloroethyl sulfinyl, 3,3,3-trifluoropropyl sulfinyl, heptafluoropropyl sulfinyl, 1,1,1,3,3,3-hexafluoro-2-propyl sulfinyl, heptafluoro-2-propyl sulfinyl, or 4,4,4-trifluorobutyl sulfinyl.

[0087] In this invention, unless otherwise specified, "C1~C6 haloalkylsulfonyl" means that the haloalkyl part is (C1~C6 haloalkyl)-S(O)2- group as described above. Examples include fluoromethanesulfonyl, difluoromethanesulfonyl, trifluoromethanesulfonyl, trichloromethanesulfonyl, 2,2,2-trifluoroethanesulfonyl, pentafluoroethanesulfonyl, 2,2,2-trichloroethanesulfonyl, 3,3,3-trifluoropropanesulfonyl, heptafluoropropanesulfonyl, 1,1,1,3,3,3-hexafluoro-2-propanesulfonyl, heptafluoro-2-propanesulfonyl, or 4,4,4-trifluorobutanesulfonyl.

[0088] In this invention, unless otherwise specified, "C3~C8 cycloalkyl C1~C6 alkylthio" means that the cycloalkyl part and the alkylthio part are (C3~C8 cycloalkyl)-(C1~C6 alkylthio)- groups as described above. Examples include cyclopropylmethylthio, 2-cyclopropylethylthio, 3-cyclopropylpropylpropylthio, 4-cyclopropylbutylthio, 5-cyclopropylpentylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, or cyclooctylmethylthio.

[0089] In this invention, unless otherwise specified, "C3~C8 cycloalkyl C1~C6 alkyl sulfinyl" means that the cycloalkyl part and the alkyl sulfinyl part are (C3~C8 cycloalkyl)-(C1~C6 alkyl sulfinyl)- groups as described above. Examples include (cyclopropylmethyl)sulfinyl, (cyclobutylmethyl)sulfinyl, (cyclopentylmethyl)sulfinyl, (cyclooctylmethyl)sulfinyl, (2-cyclopropylethyl)sulfinyl, (2-cyclobutylethyl)sulfinyl, (2-cyclopentylethyl)sulfinyl, or (2-cyclooctylethyl)sulfinyl groups.

[0090] In this invention, unless otherwise specified, "C3~C8 cycloalkyl C1~C6 alkylsulfonyl" means that the cycloalkyl part and the alkylsulfonyl part are (C3~C8 cycloalkyl)-(C1~C6 alkylsulfonyl)- groups as described above. Examples include (cyclopropylmethyl)sulfonyl, (cyclobutylmethyl)sulfonyl, (cyclopentylmethyl)sulfonyl, (cyclooctylmethyl)sulfonyl, (2-cyclopropylethyl)sulfonyl, (2-cyclobutylethyl)sulfonyl, (2-cyclopentylethyl)sulfonyl or (2-cyclooctylethyl)sulfonyl groups.

[0091] In this invention, unless otherwise specified, "C1~C6 alkoxy C1~C6 alkyl thio" means that the alkoxy moiety and the alkyl thio group are (C1~C6 alkoxy)-(C1~C6 alkyl thio)- groups as described above. Examples include (2-methoxyethyl) thio, (3-methoxypropyl) thio, (2-isopropoxyethyl) thio, (2-isopropoxybutyl) thio, (5-ethoxypentyl) thio, (6-ethoxyhexyl) thio, or (1-methoxypropane-2-yl) thio.

[0092] In this invention, unless otherwise specified, "C1~C6 alkoxy C1~C6 alkyl sulfinyl" means that the alkoxy moiety and the alkyl sulfinyl moiety are (C1~C6 alkoxy)-(C1~C6 alkyl sulfinyl)- groups as described above. Examples include (2-methoxyethyl)sulfinyl, (3-methoxypropyl)sulfinyl, (2-isopropoxyethyl)sulfinyl, (2-isopropoxybutyl)sulfinyl, (5-ethoxypentyl)sulfinyl, (6-ethoxyhexyl)sulfinyl, or (1-methoxypropane-2-yl)sulfinyl groups.

[0093] In this invention, unless otherwise specified, "C1~C6 alkoxy C1~C6 alkylsulfonyl" means that the alkoxy portion and the alkylsulfonyl portion are (C1~C6 alkoxy)-(C1~C6 alkylsulfonyl)- groups as described above. Examples include (2-methoxyethyl)sulfonyl, (3-methoxypropyl)sulfonyl, (2-isopropoxyethyl)sulfonyl, (2-isopropoxybutyl)sulfonyl, (5-ethoxypentyl)sulfonyl, (6-ethoxyhexyl)sulfonyl, or (1-methoxypropane-2-yl)sulfonyl groups.

[0094] In this invention, unless otherwise specified, “C1~C6 alkylaminosulfonyl” means that the alkyl part is (C1~C6 alkyl)-NH-S(O)2- group as described above, such as methylaminosulfonyl, ethylaminosulfonyl or isobutylaminosulfonyl groups.

[0095] In this invention, unless otherwise specified, "C1~C6 alkylthio-C1~C6 alkyl" means that the alkylthio group and the alkyl group are (C1~C6 alkylthio)-(C1~C6 alkyl)- groups as described above. Examples include 1-methylthio-1-methylethyl, 1-ethylthio-1-methylethyl, 1-n-propylthio-1-methylethyl, 1-isopropylthio-1-methylethyl, 3-methylthio-2-methylpropane-2-yl, 3-ethylthio-2-methylpropane-2-yl, 3-n-propylthio-2-methylpropane-2-yl, or 3-isopropylthio-2-methylpropane-2-yl groups.

[0096] In this invention, unless otherwise specified, "C1~C6 alkyl sulfinyl C1~C6 alkyl" means that the alkyl sulfinyl portion and the alkyl portion are (C1~C6 alkyl sulfinyl)-(C1~C6 alkyl)- groups as described above. Examples include 1-methylsulfinyl-1-methylethyl, 1-ethylsulfinyl-1-methylethyl, 1-n-propylsulfinyl-1-methylethyl, 1-isopropylsulfinyl-1-methylethyl, 3-methylsulfinyl-2-methylpropane-2-yl, 3-ethylsulfinyl-2-methylpropane-2-yl, 3-n-propylsulfinyl-2-methylpropane-2-yl, or 3-isopropylsulfinyl-2-methylpropane-2-yl groups.

[0097] In this invention, unless otherwise specified, "C1~C6 alkylsulfonyl C1~C6 alkyl" means that the alkylsulfonyl portion and the alkyl portion are (C1~C6 alkylsulfonyl)-(C1~C6 alkyl)- groups as described above. Examples include 1-methanesulfonyl-1-methylethyl, 1-ethanesulfonyl-1-methylethyl, 1-n-propanesulfonyl-1-methylethyl, 1-isopropanesulfonyl-1-methylethyl, 3-methanesulfonyl-2-methylpropane-2-yl, 3-ethanesulfonyl-2-methylpropane-2-yl, 3-n-propanesulfonyl-2-methylpropane-2-yl, or 3-isopropanesulfonyl-2-methylpropane-2-yl groups.

[0098] In this invention, unless otherwise specified, "C1~C6 haloalkylthio-C1~C6 alkyl" means that the haloalkylthio group and the alkyl group are (C1~C6 haloalkylthio)-(C1~C6 alkyl)- groups as described above. Examples 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 or 3-(2,2,2-trifluoroethylthio)propyl groups.

[0099] In this invention, unless otherwise specified, "C1~C6 haloalkylsulfinyl C1~C6 alkyl" means that the haloalkylsulfinyl moiety and the alkyl moiety are (C1~C6 haloalkylsulfinyl)-(C1~C6 alkyl)- groups as described above. Examples include (difluoromethylsulfinyl)methyl, (trifluoromethylsulfinyl)methyl, (2,2-difluoroethylsulfinyl)methyl, (2,2,2-trifluoroethylsulfinyl)methyl, and (2,2,2-trifluoroethylsulfinyl)methyl. The group includes sulfonyl)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 or 3-(2,2,2-trifluoroethylsulfinyl)propyl groups.

[0100] In this invention, unless otherwise specified, "C1~C6 haloalkylsulfonyl C1~C6 alkyl" means that the haloalkylsulfonyl portion and the alkyl portion are (C1~C6 haloalkylsulfonyl)-(C1~C6 alkyl)- groups as described above. Examples include (difluoromethanesulfonyl)methyl, (trifluoromethanesulfonyl)methyl, (2,2-difluoroethanesulfonyl)methyl, (2,2,2-trifluoroethanesulfonyl)methyl, 2-(difluoromethanesulfonyl)ethyl, 2-(trifluoromethanesulfonyl)ethyl, 2-(2,2-difluoroethanesulfonyl)ethyl, 2-(2,2,2-trifluoroethanesulfonyl)ethyl, 3-(difluoromethanesulfonyl)propyl, 3-(trifluoromethanesulfonyl)propyl, 3-(2,2-difluoroethanesulfonyl)propyl or 3-(2,2,2-trifluoroethanesulfonyl)propyl groups.

[0101] In this invention, unless otherwise specified, "C3~C8 cycloalkylthio-C1~C6 alkyl" means that the cycloalkylthio group and the alkyl group are (C3~C8 cycloalkylthio)-(C1~C6 alkyl)- groups as described above. Examples include (cyclopropylthio)methyl, (cyclobutylthio)methyl, (cyclopentylthio)methyl, (cyclohexylthio)methyl, (cyclooctylthio)methyl, 1-(cyclopropylthio)ethyl or 2-(cyclopropylthio)ethyl groups.

[0102] In this invention, unless otherwise specified, "C3~C8 cycloalkyl sulfinyl C1~C6 alkyl" means that the cycloalkyl sulfinyl moiety and the alkyl moiety are (C3~C8 cycloalkyl sulfinyl)-(C1~C6 alkyl)- groups as described above. Examples include (cyclopropyl sulfinyl)methyl, (cyclobutyl sulfinyl)methyl, (cyclopentyl sulfinyl)methyl, (cyclohexyl sulfinyl)methyl, (cyclooctyl sulfinyl)methyl, 1-(cyclopropyl sulfinyl)ethyl, or 2-(cyclopropyl sulfinyl)ethyl groups.

[0103] In this invention, unless otherwise specified, "C3~C8 cycloalkylsulfonyl C1~C6 alkyl" means that the cycloalkylsulfonyl moiety and the alkyl moiety are (C3~C8 cycloalkylsulfonyl)-(C1~C6 alkyl)- groups as described above. Examples include (cyclopropanesulfonyl)methyl, (cyclobutanesulfonyl)methyl, (cyclopentanesulfonyl)methyl, (cyclohexanesulfonyl)methyl, (cyclooctanesulfonyl)methyl, 1-(cyclopropanesulfonyl)ethyl, or 2-(cyclopropanesulfonyl)ethyl groups.

[0104] In this invention, unless otherwise specified, "C1~C6 alkoxycarbonyl C1~C6 alkyl" means that the alkoxy moiety and the alkyl moiety are (C1~C6 alkoxy)-C(O)-(C1~C6 alkyl)- groups as described above. Examples 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, or 2-(tert-butoxycarbonyl)ethyl groups.

[0105] In this invention, unless otherwise specified, “C1~C6 alkylamino C1~C6 alkyl” means that the alkyl part is (C1~C6 alkyl)-NH-(C1~C6 alkyl)- group as described above, such as (methylamino)methyl, (ethylamino)methyl, (isopropylamino)methyl, (tert-butylamino)methyl, 1-(methylamino)ethyl or 2-(methylamino)ethyl groups.

[0106] In this invention, unless otherwise specified, "C1~C6 alkoxycarbonylamino C1~C6 alkyl" means that the alkoxy part and the alkyl part are (C1~C6 alkoxy)-C(O)-NH-(C1~C6 alkyl)- group as described above, such as methoxycarbonylaminomethyl, ethoxycarbonylaminomethyl, isopropoxycarbonylaminomethyl, tert-butoxycarbonylaminomethyl or isobutoxycarbonylaminomethyl groups.

[0107] In this invention, unless otherwise specified, “C1~C6 alkyl carbonyl C1~C6 alkyl” means that the alkyl part is (C1~C6 alkyl)-C(O)-(C1~C6 alkyl)- group as described above, such as acetylmethyl, propionylmethyl, isopropyl carbonylmethyl or tert-butyl carbonylmethyl groups.

[0108] In this invention, unless otherwise specified, "aminosulfonylamino C1~C6 alkyl" means that the alkyl part is H2N-S(O)2-NH-(C1~C6 alkyl)- group as described above, such as (aminosulfonylamino)methyl, 1-(aminosulfonylamino)ethyl, 2-(aminosulfonylamino)ethyl or 3-(aminosulfonylamino)propyl groups.

[0109] In this invention, unless otherwise specified, "C1~C6 haloalkylsulfonylaminoC1~C6 alkyl" means that the haloalkyl part and the alkyl part are (C1~C6 haloalkyl)-S(O)2-NH-(C1~C6 alkyl)- group as described above, such as [(trifluoromethyl)sulfonylamino]methyl, [(2,2,2-trifluoroethyl)sulfonylamino]methyl or 3-[(trifluoromethyl)sulfonylamino]propyl group.

[0110] In this invention, unless otherwise specified, "C1~C6 alkylaminosulfonyl C1~C6 alkyl" means that the alkyl part is (C1~C6 alkyl)-NH-S(O)2-(C1~C6 alkyl)-yl, for example (N-methylaminosulfonyl)methyl, (N-ethylaminosulfonyl)methyl, (N-n-propylaminosulfonyl)methyl, (N-isopropylaminosulfonyl)methyl or 2-(N-methylaminosulfonyl)ethyl and other groups.

[0111] In this invention, unless otherwise specified, “C3~C8 cycloalkylamino C1~C6 alkyl” means that the cycloalkyl part and the alkyl part are (C3~C8 cycloalkyl)-NH-(C1~C6 alkyl)- group as described above, such as (cyclopropylamino)methyl, (cyclobutylamino)methyl, 1-(cyclopropylamino)ethyl or 2-(cyclopropylamino)ethyl groups.

[0112] In this invention, unless otherwise specified, "C1~C6 haloalkylaminoC1~C6 alkyl" means that the haloalkyl part and the alkyl part are (C1~C6 haloalkyl)-NH-(C1~C6 alkyl)- group as described above, such as (trifluoromethylamino)methyl, (2,2-difluoroethylamino)methyl, (2,2,2-trifluoroethylamino)methyl, 1-(trifluoromethylamino)ethyl or 2-(trifluoromethylamino)ethyl groups.

[0113] In this invention, unless otherwise specified, "C1~C6 alkylsulfonylamino C1~C6 alkyl" means that the alkyl carbonyl amino part and the alkyl part are (C1~C6 alkyl)-S(O)2-NH-(C1~C6 alkyl)- group as described above, and examples include methanesulfonylaminomethyl, ethanesulfonylaminomethyl, isopropanesulfonylaminomethyl or (2-methanesulfonylamino)ethyl groups.

[0114] In this invention, unless otherwise specified, "C1~C6 alkoxyaminocarbonyl C1~C6 alkyl" means that the alkoxy moiety and the alkyl moiety are (C1~C6 alkoxy)-NH-C(O)-(C1~C6 alkyl)- group as described above, such as 2-(methoxyamino)-2-oxoethyl, 2-(ethoxyamino)-2-oxoethyl or 3-(methoxyamino)-3-oxopropyl groups.

[0115] In this invention, unless otherwise specified, "C1~C6 alkoxyaminocarbonyl" means that the alkoxy moiety is (C1~C6 alkoxy)-NH-C(O)- group as described above, such as methoxycarbamoyl, ethoxycarbamoyl, n-propoxycarbamoyl, n-pentoxycarbamoyl or isopropoxycarbamoyl groups.

[0116] In this invention, unless otherwise specified, "C1~C6 alkylamino" means that the alkyl part is (C1~C6 alkyl)-NH- group as described above, such as methylamino, ethylamino, n-propylamino or isopropylamino groups.

[0117] In this invention, unless otherwise specified, "C1~C6 haloalkylamino" means that the haloalkyl part is (C1~C6 haloalkyl)-NH- group as described above, such as 2-fluoroethylamino, 2,2-difluoroethylamino, 2,2,2-trifluoroethylamino, 2,2,2-trichloroethylamino, pentafluoroethylamino, 3,3,3-trifluoropropylamino or 1,1,1,3,3,3-hexafluoro-2-propylamino and other groups.

[0118] In this invention, unless otherwise specified, "C3~C8 cycloalkylamino" means that the cycloalkyl part is (C3~C8 cycloalkyl)-NH- group as described above, such as cyclopropylamino, cyclobutylamino, cyclopentamino, cyclohexylamino, cycloheptamino or cyclooctamino groups.

[0119] In this invention, unless otherwise specified, "C1~C6 alkylaminocarbonyl" means that the alkyl part is (C1~C6 alkyl)-NH-C(O)- group as described above. Examples include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, isobutylaminocarbonyl, sec-butylaminocarbonyl, tert-butylaminocarbonyl, n-pentanaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 1-ethylpropylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, or n-hexylaminocarbonyl.

[0120] In this invention, unless otherwise specified, "C3~C8 cycloalkylaminocarbonyl" means that the cycloalkyl part is (C3~C8 cycloalkyl)-NH-C(O)- group as described above, such as cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentanaminocarbonyl, cyclohexylaminocarbonyl, cycloheptanaminocarbonyl or cyclooctylaminocarbonyl groups.

[0121] In this invention, unless otherwise specified, "C1~C6 alkylaminothiocarbonyl" means that the alkyl part is (C1~C6 alkyl)-NH-C(S)- group as described above. Examples include methylamino (thiocarbonyl), ethylamino (thiocarbonyl), n-propylamino (thiocarbonyl), isopropylamino (thiocarbonyl), n-butylamino (thiocarbonyl), isobutylamino (thiocarbonyl), sec-butylamino (thiocarbonyl), tert-butylamino (thiocarbonyl), n-pentanamino (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), or n-hexylamino (thiocarbonyl).

[0122] In this invention, unless otherwise specified, "C1~C6 alkoxy C1~C6 alkyl carbonyl" means that the alkoxy moiety and the alkyl moiety are (C1~C6 alkoxy)-(C1~C6 alkyl)-C(O)- groups as described above. Examples include methoxyacetyl, ethoxyacetyl, propoxyacetyl, isopropoxyacetyl, butoxyacetyl, 2-methoxypropionyl, 3-methoxypropionyl, 2-ethoxypropionyl, 3-ethoxypropionyl, 2-methoxybutyryl, 4-methoxybutyryl, 2-methoxyvalerate, or 5-methoxyvalerate.

[0123] In this invention, unless otherwise specified, “C1~C6 alkyl carbonyl thiogroup” means that the alkyl part is (C1~C6 alkyl)-C(O)-S-group as described above, such as methyl carbonyl thiogroup, ethyl carbonyl thiogroup, propyl carbonyl thiogroup or isopropyl carbonyl thiogroup and other groups.

[0124] In this invention, unless otherwise specified, “C1~C6 alkyl carbonyl amino” means that the alkyl part is (C1~C6 alkyl)-C(O)-NH- group as described above, such as acetylamino, propionylamino, butyrylamino or isobutyrylamino groups.

[0125] In this invention, unless otherwise specified, "C1~C6 alkoxycarbonylamino" means that the alkoxy moiety is (C1~C6 alkoxy)-C(O)-NH- group as described above, such as methoxycarbonylamino, ethoxycarbonylamino, isopropoxycarbonylamino, tert-butoxycarbonylamino or isobutoxycarbonylamino groups.

[0126] In this invention, unless otherwise specified, “C1~C6 alkylamino carbonylamino” means that the alkyl part is (C1~C6 alkyl)-NH-C(O)-NH- group as described above, such as methylaminocarbonylamino, ethylaminocarbonylamino, n-propylaminocarbonylamino, isopropylaminocarbonylamino or tert-butylaminocarbonylamino groups.

[0127] In this invention, unless otherwise specified, “C1~C6 alkylsulfonylamino” means that the alkyl part is (C1~C6 alkyl)-S(O)2-NH- group as described above, such as methanesulfonylamino, ethanesulfonylamino, n-propanesulfonylamino, isopropanesulfonylamino or tert-butanesulfonylamino groups.

[0128] In this invention, unless otherwise specified, "C1~C6 haloalkylsulfonylamino" means that the haloalkyl part is (C1~C6 haloalkyl)-S(O)2-NH- group as described above. Examples include fluoromethanesulfonylamino, difluoromethanesulfonylamino, trifluoromethanesulfonylamino, chloromethanesulfonylamino, trichloromethanesulfonylamino, 2,2,2-trifluoroethanesulfonylamino, 2,2-difluoroethanesulfonylamino, or 3,3,3-trifluoropropanesulfonylamino.

[0129] In this invention, unless otherwise specified, “C1~C6 alkylaminosulfonylamino” means that the alkyl part is (C1~C6 alkyl)-NH-S(O)2-NH- group as described above, such as methylaminosulfonylamino, ethylaminosulfonylamino, n-propylaminosulfonylamino, isopropylaminosulfonylamino or tert-butylaminosulfonylamino groups.

[0130] In this invention, unless otherwise specified, "5-12-membered heteroarylamino" means that the heteroaryl moiety is (5-12-membered heteroaryl)-NH- group as described above. Examples include pyridinylamino, pyrimidinylamino, pyrazinylamino, pyridazinylamino, triazinylamino, thiophenylamino, furanylamino, pyrroleylamino, pyrazolylamino, thiazolylamino, isothiazolylamino, oxazolylamino, isoxazolylamino, imidazoleylamino, triazolylamino, thiadiazolylamino, oxadiazolylamino, or tetrazolylamino groups.

[0131] In this invention, unless otherwise specified, "C6~C" 12"Aryl C1~C6 alkyl" indicates that the aryl moiety and the alkyl moiety are (C6~C6) as described above. 12 Aryl)-(C1~C6 alkyl)-yl, for example, benzyl, 1-phenylethyl, 2-phenylethyl, 2-phenylpropyl, 2-phenylbutyl, 1-phenylpentyl, naphth-1-ylmethyl or naphth-2-ylmethyl groups.

[0132] In this invention, unless otherwise specified, "5-12-membered heteroaryl C1-C6 alkyl" means that the heteroaryl portion and the alkyl portion are (5-12-membered heteroaryl)-(C1-C6 alkyl)- groups as described above. Examples include pyridylmethyl, pyrimidinylmethyl, pyrazinylmethyl, pyridazinylmethyl, triazinylmethyl, thienylmethyl, furanylmethyl, pyrroleylmethyl, pyrazolylmethyl, thiazolylmethyl, isothiazolylmethyl, oxazolylmethyl, isoxazolylmethyl, imidazoleylmethyl, triazolylmethyl, thiadiazolylmethyl, oxadiazolylmethyl, tetrazolylmethyl, indolylmethyl, benzimidazoleylmethyl, inzolylmethyl, and benzotriazole. The group includes methyl, isoquinolinylmethyl, quinolinylmethyl, benzothiazolylmethyl, benzofuranylmethyl, benzothiophenylmethyl, benzoisoxazolylmethyl, pyrazolopyridylmethyl, pyrazolopyrimidylmethyl, pyrrolopyridylmethyl, triazololopyridylmethyl, triazololopyrimidylmethyl, quinazolinylmethyl, quinoxolinylmethyl, 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 or 2-thiadiazolyl-2-propyl groups.

[0133] In this invention, unless otherwise specified, "3-6 membered heterocyclic C1-C6 alkyl" means that the heterocyclic group and the alkyl group are (3-6 membered heterocyclic)-(C1-C6 alkyl)- groups as described above. Examples include azircyclopropanemethyl, ethylene oxidemethyl, oxacyclobutanemethyl, thiocyclobutanemethyl, tetrahydrofuranylmethyl, tetrahydropyranylmethyl, azircyclobutanemethyl, pyrrolidinemethyl, piperidinylmethyl, piperazinemethyl, dihydroisoxazolylmethyl, dioxaborylmethyl, dioxopentylmethyl, dioxylmethyl or morpholinylmethyl groups.

[0134] In this invention, unless otherwise specified, "C6~C" 12 "Aryloxy group" indicates that the aryl moiety has the above meaning (C6~C6). 12 Aryl)-O-yl, for example, phenoxy, 2-biphenyloxy, 4-biphenyloxy, naphth-1-yloxy or naphth-2-yloxy groups.

[0135] In this invention, unless otherwise specified, "5-12-membered heteroaryloxy" means that the heteroaryl moiety is (5-12-membered heteroaryl)-O- group as described above. Examples 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, (pyridazine-3-yl)oxy, (pyridazine-4-yl)oxy, (pyrazine-2-yl)oxy, (1,3,5-triazine-2-yl)oxy, (thiazolium-2-yl)oxy, (thiazolium-4-yl)oxy, (thiazolium-5-yl)oxy, (pyrazolium-1-yl)oxy, (pyrazolium-3-yl)oxy, (pyrazolium-4-yl)oxy, or (pyrazolium-5-yl)oxy groups.

[0136] In this invention, unless otherwise specified, "3-6 membered heterocyclic oxy group" means that the heterocyclic group is a (3-6 membered heterocyclic)-O- group as described above. Examples include azircyclopropaneoxy group, epoxyethoxy group, oxacyclobutaneoxy group, thiocyclobutaneoxy group, tetrahydrofuranyloxy group, tetrahydropyranyloxy group, azircyclobutaneoxy group, pyrrolidineoxy group, piperidinyloxy group, piperazineyloxy group, dihydroisooxazolyloxy group, dioxaboryloxy group, dioxopentyloxy group, dioxyloxy group, or morpholinyloxy group.

[0137] In this invention, unless otherwise specified, "C6~C" 12 "Aryloxy C1~C6 alkyl" indicates that the aryloxy moiety and the alkyl moiety are (C6~C6) as described above. 12 Aryloxy)-(C1~C6 alkyl)-yl, for example, phenoxymethyl, 1-phenoxyethyl, 2-phenoxyethyl, (naphth-1-yloxy)methyl or (naphth-2-yloxy)methyl groups.

[0138] In this invention, unless otherwise specified, "5-12-membered heteroaryloxy C1-C6 alkyl" means that the heteroaryloxy moiety and the alkyl moiety are (5-12-membered heteroaryloxy)-(C1-C6 alkyl)-yl as described above. Examples include (pyridin-2-yloxy)methyl, (pyridin-3-yloxy)methyl, (pyridin-4-yloxy)methyl, (pyrimidin-2-yloxy)methyl, (pyrimidin-4-yloxy)methyl, and (pyrimidin-5-yloxy)methyl. The group may contain methyl, (pyrazine-3-yloxy)methyl, (pyrazine-4-yloxy)methyl, (pyrazine-2-yloxy)methyl, (1,3,5-triazine-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, or 2-(pyridin-3-yloxy)ethyl groups.

[0139] In this invention, unless otherwise specified, "3-6 membered heterocyclic oxy group C1-C6 alkyl" means that the heterocyclic oxy group is (3-6 membered heterocyclic group)-(C1-C6 alkyl)- group as described above. Examples include (azacyclopropaneoxy)methyl, (epoxyethyleneoxy)methyl, (oxacyclobutaneoxy)methyl, (thiocyclobutaneoxy)methyl, (tetrahydrofuranyloxy)methyl, (tetrahydropyranyloxy)methyl, (azacyclobutaneoxy)methyl, (pyrrolidineoxy)methyl, (piperidinyloxy)methyl, (piperazinyloxy)methyl, (dihydroisoxazolyloxy)methyl, (dioxaboryloxy)methyl, (dioxopentyloxy)methyl, (dioxaneoxy)methyl, or (morpholinyloxy)methyl groups.

[0140] In this invention, unless otherwise specified, "C6~C" 12 "Arylthio" indicates that the aryl moiety has the above-mentioned meaning (C6~C6). 12 Aryl)-S-yl, for example, phenylthio, 2-biphenylthio, 4-biphenylthio, naphth-1-ylthio or naphth-2-ylthio groups.

[0141] In this invention, unless otherwise specified, "C6~C" 12 "Arylsulfinyl" indicates that the aryl moiety has the above meaning (C6~C6). 12 Aryl)-S(O)- group, for example, phenylsulfinyl, 2-biphenylsulfinyl, 4-biphenylsulfinyl, naphth-1-ylsulfinyl or naphth-2-ylsulfinyl groups.

[0142] In this invention, unless otherwise specified, "C6~C" 12 "Arylsulfonyl" indicates that the aryl moiety has the above meaning (C6~C6). 12 Aryl)-S(O)2-yl, for example, phenylsulfonyl, 2-biphenylsulfonyl, 4-biphenylsulfonyl, naphth-1-ylsulfonyl or naphth-2-ylsulfonyl groups.

[0143] In this invention, unless otherwise specified, "5-12-membered heteroarylthio" means that the heteroaryl moiety is a (5-12-membered heteroaryl)-S-group as described above. Examples include pyridylthio, pyrimidinylthio, pyrazinylthio, pyridazinylthio, triazinylthio, thiopheneylthio, furanylthio, pyrroleylthio, pyrazolylthio, thiazolylthio, isothiazolylthio, oxazolylthio, isoxazolylthio, imidazoleylthio, triazolylthio, and thiadiazoleyl. Thioyl, oxadiazolylthio, tetrazolylthio, indolylthio, benzimidazolylthio, indazolylthio, benzotriazolylthio, isoquinolinylthio, quinolinylthio, benzothiazolylthio, benzofuranylthio, benzothiophenylthio, benzoisooxazolylthio, pyrazolopyridylthio, pyrazolopyrimidinylthio, pyrrolopyridylthio, triazolopyridylthio, triazolopyrimidinylthio, quinazolinylthio, quinoxolinylthio, or cinolinylthio, etc.

[0144] In this invention, unless otherwise specified, "5-12-membered heteroarylsulfinyl" indicates that the heteroaryl moiety is (5-12-membered heteroaryl)-S(O)- group as described above. Examples include pyridylsulfinyl, pyrimidinylsulfinyl, pyrazinylsulfinyl, pyridazinylsulfinyl, triazinylsulfinyl, thiopheneylsulfinyl, furanylsulfinyl, pyrrolidinylsulfinyl, pyrazolylsulfinyl, pyrazolylsulfinyl, thiazolylsulfinyl, isothiazolylsulfinyl, oxazolylsulfinyl, isoxazolylsulfinyl, imidazoleylsulfinyl, triazolylsulfinyl, and thiadiazolylsulfinyl. The group includes oxadiazolyl sulfinyl, tetrazolyl sulfinyl, indoleyl sulfinyl, benzimidazolyl sulfinyl, indazolyl sulfinyl, benzotriazolyl sulfinyl, isoquinolinyl sulfinyl, quinolinyl sulfinyl, benzothiazolyl sulfinyl, benzofuranyl sulfinyl, benzothiophenyl sulfinyl, benzoisooxazolyl sulfinyl, pyrazolopyridyl sulfinyl, pyrazolopyrimidine sulfinyl, pyrrolopyridyl sulfinyl, triazolopyridyl sulfinyl, triazolopyrimidine sulfinyl, quinazolinyl sulfinyl, quinoxolinyl sulfinyl, or cinnamolineyl sulfinyl, etc.

[0145] In this invention, unless otherwise specified, "5-12-membered heteroarylsulfonyl" indicates that the heteroaryl moiety is (5-12-membered heteroaryl)-S(O)2- group as described above. Examples include pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl, pyridazinylsulfonyl, triazinylsulfonyl, thiopheneylsulfonyl, furanylsulfonyl, pyrroleylsulfonyl, pyrazolylsulfonyl, thiazolylsulfonyl, isothiazolylsulfonyl, oxazolylsulfonyl, isoxazolylsulfonyl, imidazoleylsulfonyl, triazolylsulfonyl, and thiadiazolylsulfonyl. Acyl, oxadiazolylsulfonyl, tetrazolylsulfonyl, indoleylsulfonyl, benzimidazolylsulfonyl, indazolylsulfonyl, benzotriazolylsulfonyl, isoquinolinylsulfonyl, quinolinylsulfonyl, benzothiazolylsulfonyl, benzofuranylsulfonyl, benzothiophenylsulfonyl, benzoisooxazolylsulfonyl, pyrazolopyridylsulfonyl, pyrazolopyrimidinesulfonyl, pyrrolopyridylsulfonyl, triazolopyridylsulfonyl, triazolopyrimidinesulfonyl, quinazolinylsulfonyl, quinoxalinylsulfonyl or cinnamolineylsulfonyl groups, etc.

[0146] In this invention, unless otherwise specified, "3-6 membered heterocyclic thiogroup" means that the heterocyclic group is a (3-6 membered heterocyclic)-S-group as described above. Examples include azirrocyclopropane thiogroup, epoxy ethylene thiogroup, oxocyclobutane thiogroup, thiocyclobutane thiogroup, tetrahydrofuranyl thiogroup, tetrahydropyranyl thiogroup, azirrocyclobutane thiogroup, pyrrolidine thiogroup, piperidinyl thiogroup, piperazine thiogroup, dihydroisooxazolyl thiogroup, dioxaboryl thiogroup, dioxopentaneyl thiogroup, dioxane thiogroup, or morpholinyl thiogroup.

[0147] In this invention, unless otherwise specified, "3-6 membered heterocyclic sulfinyl" means that the heterocyclic group is a (3-6 membered heterocyclic)-S(O)- group as described above. Examples include azircyclic propane sulfinyl, epoxy ethylene sulfinyl, oxetane butyl sulfinyl, thiocyclobutane sulfinyl, tetrahydrofuranyl sulfinyl, tetrahydropyranyl sulfinyl, azircyclic butyl sulfinyl, pyrrolidinyl sulfinyl, piperidinyl sulfinyl, piperazine sulfinyl, dihydroisooxazolyl sulfinyl, dioxaboryl sulfinyl, dioxopentane sulfinyl, dioxylalkyl sulfinyl, or morpholinyl sulfinyl.

[0148] In this invention, unless otherwise specified, "3-6 membered heterocyclic sulfonyl" means that the heterocyclic group is (3-6 membered heterocyclic)-S(O)2- group as described above. Examples include aziridine propanesulfonyl, epoxy ethylene sulfonyl, oxadiazine sulfonyl, thiocyclobutane sulfonyl, tetrahydrofuranyl sulfonyl, tetrahydropyranyl sulfonyl, aziridine butyl sulfonyl, pyrrolidinyl sulfonyl, piperidinyl sulfonyl, piperazine sulfonyl, dihydroisooxazolyl sulfonyl, dioxaboryl sulfonyl, dioxopentaneyl sulfonyl, dioxyl sulfonyl, or morpholinyl sulfonyl.

[0149] In this invention, unless otherwise specified, "C6~C" 12 "Aryl carbonyl" indicates that the aryl moiety has the above meaning (C6~C6). 12 Aryl)-C(O)- group, for example, benzoyl, 2-biphenylcarbonyl, 4-biphenylcarbonyl, naphth-1-ylcarbonyl or naphth-2-ylcarbonyl groups.

[0150] In this invention, unless otherwise specified, "C6~C" 12 "Aryloxycarbonyl" indicates that the aryloxy moiety and the carbonyl moiety are as described above (C6~C6). 12 Aryloxy)-C(O)- group, for example, phenoxycarbonyl, 2-biphenyloxycarbonyl, 4-biphenyloxycarbonyl, naphth-1-yloxycarbonyl or naphth-2-yloxycarbonyl groups.

[0151] In this invention, unless otherwise specified, "5-12-membered heteroaryl carbonyl" means that the heteroaryl moiety is a (5-12-membered heteroaryl)-C(O)- group as described above. Examples include pyridyl carbonyl, pyrimidinyl carbonyl, pyrazinyl carbonyl, pyridazinyl carbonyl, triazinyl carbonyl, thiophenyl carbonyl, furanyl carbonyl, pyrroleyl carbonyl, pyrazolyl carbonyl, thiazolyl carbonyl, isothiazolyl carbonyl, oxazolyl carbonyl, isoxazolyl carbonyl, imidazoleyl carbonyl, triazolyl carbonyl, and thiadiazole. The group includes alkyl carbonyl, oxadiazolyl carbonyl, tetrazolyl carbonyl, indolyl carbonyl, benzimidazolyl carbonyl, indazole carbonyl, benzotriazolyl carbonyl, isoquinolinyl carbonyl, quinolinyl carbonyl, benzothiazolyl carbonyl, benzofuranyl carbonyl, benzothiophenyl carbonyl, benzoisooxazolyl carbonyl, pyrazolopyridyl carbonyl, pyrazolopyridyl carbonyl, pyrrolopyridyl carbonyl, triazolopyridyl carbonyl, triazolopyridyl carbonyl, quinazolinyl carbonyl, quinoxolinyl carbonyl, or terpineyl carbonyl, etc.

[0152] In this invention, unless otherwise specified, "5-12-membered heteroaryloxycarbonyl" means that the heteroaryl moiety is (5-12-membered heteroaryloxy)-C(O)- group as described above. Examples include pyridyloxycarbonyl, pyrimidinyloxycarbonyl, pyrazinyloxycarbonyl, pyridazinyloxycarbonyl, triazinyloxycarbonyl, thiophenyloxycarbonyl, furanyloxycarbonyl, pyrrolithyloxycarbonyl, pyrazolyloxycarbonyl, thiazolyloxycarbonyl, isothiazolyloxycarbonyl, oxazolyloxycarbonyl, isoxazolyloxycarbonyl, imidazoleyloxycarbonyl, triazolyloxycarbonyl, and thiadiazolyloxycarbonyl. The group includes alkyl, diazolyloxycarbonyl, tetrazolyloxycarbonyl, indolyloxycarbonyl, benzimidazolyloxycarbonyl, indazolyloxycarbonyl, benzotriazolyloxycarbonyl, isoquinolinyloxycarbonyl, quinolinyloxycarbonyl, benzothiazolyloxycarbonyl, benzofuranyloxycarbonyl, benzothiophenyloxycarbonyl, benzoisooxazolyloxycarbonyl, pyrazolopyridyloxycarbonyl, pyrazolopyrimidinyloxycarbonyl, pyrrolopyridyloxycarbonyl, triazololopyridyloxycarbonyl, triazololopyrimidinyloxycarbonyl, quinazolinyloxycarbonyl, quinoxolinyloxycarbonyl, or cinnamonyloxycarbonyl, etc.

[0153] In this invention, unless otherwise specified, "3-6 membered heterocyclic carbonyl" means that the heterocyclic group is a (3-6 membered heterocyclic)-C(O)- group as described above. Examples include azirrocyclopropane carbonyl, ethylene oxide carbonyl, oxocyclobutane carbonyl, thiocyclobutane carbonyl, tetrahydrofuranyl carbonyl, tetrahydropyranyl carbonyl, azirrocyclobutane carbonyl, pyrrolidine carbonyl, piperidinyl carbonyl, piperazine carbonyl, dihydroisooxazolyl carbonyl, dioxaboryl carbonyl, dioxopentaneyl carbonyl, dioxoalkyl carbonyl, or morpholinyl carbonyl.

[0154] In this invention, unless otherwise specified, "C6~C" 12 "Aryl C1~C6 alkyl carbonyl" indicates that the aryl moiety and the alkyl moiety are (C6~C6) as described above. 12 Aryl)-(C1~C6 alkyl)-C(O)-yl, for example, benzyl carbonyl, (1-phenylethyl) carbonyl, (2-phenylethyl) carbonyl, (naphth-1-ylmethyl) carbonyl or (naphth-2-ylmethyl) carbonyl groups.

[0155] In this invention, unless otherwise specified, "5-12-membered heteroaryl C1-C6 alkyl carbonyl" means that both the heteroaryl moiety and the alkyl moiety are (5-12-membered heteroaryl)-(C1-C6 alkyl)-C(O)- groups as described above. Examples include (pyridinylmethyl)carbonyl, (pyrimidinylmethyl)carbonyl, (pyrazinylmethyl)carbonyl, (pyridazinylmethyl)carbonyl, (triazinylmethyl)carbonyl, (thienylmethyl)carbonyl, and ( Furanylmethyl)carbonyl, (pyrroleylmethyl)carbonyl, (pyrazolylmethyl)carbonyl, (thiazolylmethyl)carbonyl, (isothiazolylmethyl)carbonyl, (oxazolylmethyl)carbonyl, (isooxazolylmethyl)carbonyl, (imidazolylmethyl)carbonyl, (triazolylmethyl)carbonyl, (thiadiazolylmethyl)carbonyl, (oxadiazolylmethyl)carbonyl, (tetrazoleylmethyl)carbonyl, (quinazolinylmethyl)carbonyl, or (quinoxolinylmethyl)carbonyl, etc.

[0156] In this invention, unless otherwise specified, "3-6 membered heterocyclic C1-C6 alkyl carbonyl" means that the heterocyclic group and the alkyl group are (3-6 membered heterocyclic)-(C1-C6 alkyl)-C(O)- groups as described above. Examples include (epoxyalkylmethyl)carbonyl, (oxocyclic butylmethyl)carbonyl, (thiocyclic butylmethyl)carbonyl, (tetrahydrofuranylmethyl)carbonyl, (tetrahydropyranylmethyl)carbonyl, (azacyclic butylmethyl)carbonyl, (pyrrolidinemethyl)carbonyl, (piperidinylmethyl)carbonyl, (piperazinylmethyl)carbonyl, (dioxolanecyclomethyl)carbonyl, (dioxoalkylmethyl)carbonyl, or (morpholinylmethyl)carbonyl groups.

[0157] In this invention, unless otherwise specified, "C6~C" 12 "Arylaminocarbonyl" indicates that the aryl moiety has the above meaning (C6~C6). 12 Aryl)-NH-C(O)- group, for example (phenylamino)carbonyl, (naphth-1-ylamino)carbonyl or (naphth-2-ylamino)carbonyl groups.

[0158] In this invention, unless otherwise specified, "5-12-membered heteroarylaminocarbonyl" means that the heteroaryl moiety is (5-12-membered heteroaryl)-NH-C(O)- group as described above. Examples include (pyridinylamino)carbonyl, (pyrimidinylamino)carbonyl, (pyrazinylamino)carbonyl, (pyridazinylamino)carbonyl, (triazinylamino)carbonyl, (thiophenylamino)carbonyl, (furanylamino)carbonyl, (pyrroleylamino)carbonyl, (pyrazolylamino)carbonyl, (thiazolylamino)carbonyl, (isothiazolylamino)carbonyl, (oxazolylamino)carbonyl, (isooxazolylamino)carbonyl, (imidazolylamino)carbonyl, (triazolylamino)carbonyl, (thiadiazolylamino)carbonyl, (oxadiazolylamino)carbonyl, or (tetrazolylamino)carbonyl groups.

[0159] In this invention, unless otherwise specified, "3-6 membered heterocyclic amino carbonyl" means that the heteroaryl moiety is a (3-6 membered heterocyclic)-NH-C(O)- group as described above. Examples include (epoxyethylene amino) carbonyl, (oxocyclic butylamino) carbonyl, (thiocyclic butylamino) carbonyl, (tetrahydrofuranylamino) carbonyl, (tetrahydropyranylamino) carbonyl, (azacyclic butylamino) carbonyl, (pyrrolidineamino) carbonyl, (piperidinylamino) carbonyl, (dioxolaneamino) carbonyl, (dioxoalkylamino) carbonyl, or (morpholinylamino) carbonyl.

[0160] In this invention, unless otherwise specified, "C6~C" 12 "Arylaminocarbonyl C1~C6 alkyl" indicates that the aryl moiety and the alkyl moiety are (C6~C6) as described above. 12 Aryl)-NH-C(O)-(C1~C6 alkyl)-yl, for example (phenylaminocarbonyl)methyl, (naphth-1-ylaminocarbonyl)methyl, (naphth-2-ylaminocarbonyl)methyl or 2-(phenylaminocarbonyl)ethyl groups.

[0161] In this invention, unless otherwise specified, "C6~C" 12 "Aryl carbonyl C1~C6 alkyl" indicates that the aryl moiety and the alkyl moiety are (C6~C6) as described above. 12 Aryl)-C(O)-(C1~C6 alkyl)-yl, for example (phenylcarbonyl)methyl, (naphth-1-ylcarbonyl)methyl, (naphth-2-ylcarbonyl)methyl or 2-(phenylcarbonyl)ethyl groups.

[0162] In this invention, unless otherwise specified, "5-12-membered heteroarylcarbonyl C1-C6 alkyl" means that the heteroaryl portion and the alkyl portion are (5-12-membered heteroaryl)-C(O)-(C1-C6 alkyl)-group as described above. Examples include (pyridylcarbonyl)methyl, (pyrimidinylcarbonyl)methyl, (pyrazinylcarbonyl)methyl, (pyridazinylcarbonyl)methyl, (triazinylcarbonyl)methyl, (thienylcarbonyl)methyl, (furanylcarbonyl)methyl, (pyrroleylcarbonyl)methyl, (pyrazolylcarbonyl)methyl, (thiazolylcarbonyl)methyl, (isothiazolylcarbonyl)methyl, (oxazolylcarbonyl)methyl, (isooxazolylcarbonyl)methyl, (imidazolylcarbonyl)methyl, (triazolylcarbonyl)methyl, (thiadiazolylcarbonyl)methyl, (oxadiazolylcarbonyl)methyl, or (tetrazolylcarbonyl)methyl groups.

[0163] In this invention, unless otherwise specified, "3-6 membered heterocyclic carbonyl C1-C6 alkyl" means that the heterocyclic group and the alkyl group are (3-6 membered heterocyclic)-C(O)-(C1-C6 alkyl)- group as described above. Examples include (epoxyalkylcarbonyl)methyl, (oxocyclic butylcarbonyl)methyl, (thiocyclic butylcarbonyl)methyl, (tetrahydrofuranylcarbonyl)methyl, (tetrahydropyranylcarbonyl)methyl, (azacyclic butylcarbonyl)methyl, (pyrrolidinecarbonyl)methyl, (piperidinylcarbonyl)methyl, (piperazinylcarbonyl), (dioxolanecyclocarbonyl)methyl, (dioxoalkylcarbonyl)methyl, or (morpholinylcarbonyl)methyl groups.

[0164] In this invention, "can be selected from the substituent group". α "Substitution of one or more substituents" means unsubstituted or "can be selected from the group of substituents". α "Substituted by one or more substituents". In the case of substitution by two or more substituents, selected from the substituent group. α The two or more substituents can be the same or different, and can be selected from hydrogen atom, halogen atom, hydroxyl, mercapto, amino, cyano, nitro, C1~C6 alkyl, C1~C6 haloalkyl, C3~C8 cycloalkyl (the cycloalkyl can be selected from the substituent group) β Substituents in the group), C3~C8 halocycloalkyl groups (the cycloalkyl group can be selected from the substituent group) β Substituents in the group (C1-C6 alkoxy, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C8 cycloalkyl, C2-C6 ynyl (the cycloalkyl group can be selected from the substituent group)). β Substituents in the group), C1-C6 alkoxy groups, C3-C8 cycloalkyloxy groups (the cycloalkyl group can be selected from the substituent group) β Substituents in (C1-C6 alkyl oxy, C1-C6 alkoxy, C6-C6 alkoxy) 12 aryl C1-C6 alkoxy (the aryl group may be substituted by one or more substituents selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, and cyano), C2-C6 alkenoxy, C2-C6 alkynoxy, tris(C1-C6 alkyl)silyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino (the amino group may be selected from the substituent group) c Substituents in (C1-C6 alkyl carbonyl amino groups, where the amino group can be selected from the substituent group) c Substituents in the group), C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group can be selected from the substituent group)β Substituents in the group), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl (the aryl group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (substituents in the group), substitution of one or more substituents in the cyano group), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, C1-C6 alkylamino groups (the amino group can be selected from the substituent group group) c Substituents in the group), substitution of one or more substituents in the cyano group), oxo group or -C (=NR) m )R n The base has one or more chemically acceptable substituents.

[0165] In this invention, "can be selected from the substituent group". β "Substitution of one or more substituents" means unsubstituted or "can be selected from the group of substituents". β "Substituted by one or more substituents". In the case of substitution by two or more substituents, selected from the substituent group. β The two or more substituents can be the same or different, and can be selected from hydrogen atom, halogen atom, hydroxyl, amino, cyano, C1~C6 alkyl, C3~C8 cycloalkyl (the cycloalkyl can be substituted by substituents selected from C1~C6 alkyl or C1~C6 haloalkyl), C1~C6 haloalkyl, C1~C6 alkoxy-C1~C6 alkyl, C1~C6 alkoxy, C1~C6 alkylcarbonylamino (the amino can be selected from the substituent group) c (substituents in the group), C1~C6 alkyl carbonyl, C1~C6 alkoxy carbonyl, amino carbonyl, C1~C6 alkylamino carbonyl (the amino group can be selected from the substituent group) c Substituents in (C6~C) 12 aryl (the aryl group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (substituents in the group), substitution of one or more substituents in the cyano group), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, C1-C6 alkylamino groups (the amino group can be selected from the substituent group group) c(substituents in the group), one or more substituents in the cyano group), or a 3-6 membered heterocyclic group (the heterocyclic group can be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c (Substituent substitution in the group), (substituent substitution of one or more substituents in the cyano group), (substituent substitution of one or more chemically acceptable substituents).

[0166] In this invention, "can be selected from the substituent group". c "Substitution of one or more substituents" means unsubstituted or "can be selected from the group of substituents". c "Substituted by one or more substituents". In the case of substitution by two or more substituents, selected from the substituent group. c The two or more substituents can be the same or different, and can be selected from hydrogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group can be selected from the substituent group). β The substitution of one or more chemically acceptable substituents in C1-C6 alkoxy-C1-C6 alkyl, C1-C6 haloalkyloxy-C1-C6 alkyl, cyano-C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl or C1-C6 alkoxycarbonyl.

[0167] In this invention, unless otherwise specified, "-N=C(C1~C6 alkyl)2" means that the carbon atom bonded to the nitrogen atom is replaced by two arbitrary substituents selected from the above-mentioned C1~C6 alkyl groups, and the two C1~C6 alkyl groups may be the same as each other or different from each other.

[0168] In this invention, "R" 2 With R 3 They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u "0 to 1 atoms or groups of atoms together form a 5 to 6-membered ring, which can be replaced by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 alkoxy or oxo groups. Examples of such groups are given, but not limited to them."

[0169] [Chemistry 3] In this invention, "R" a With R b They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. uThe 0 to 1 atoms or groups of atoms in the ring form a nitrogen-containing 4 to 6-membered ring, which can be replaced by one or more chemically acceptable substituents selected from halogen atoms, C1 to C6 alkyl groups, C1 to C6 haloalkyl groups, C1 to C6 alkoxy groups or oxo groups. Examples of such groups are given, but not limited to them.

[0170] [Chemistry 4] In this invention, "R" d With R e They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u "0 to 2 atoms or groups of atoms together form a 3 to 6-membered ring, which can be replaced by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 haloalkyl, C1 to C6 alkoxy or oxo" Examples of such groups are given, but not limited to them.

[0171] [Chemistry 5] (In the above formula, R) f (This means the same as above).

[0172] In this invention, "R" i With R k They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which can be oxidized by one or two oxygen atoms), and NR. u The 0 to 1 atoms or groups of atoms in the ring together form a nitrogen-containing 4 to 6-membered ring, which can be selected from halogen atoms, C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 alkyl carbonyl, C1 to C6 alkoxy carbonyl, amino carbonyl, and C1 to C6 alkyl amino carbonyl (the amino group can be selected from the substituent group). c Substituents in (C1-C6 alkyl carbonyl amino groups, where the amino group can be selected from the substituent group) c "Substituents in the group" or "chemically acceptable substitutions in the oxo group" can be exemplified by the following groups, but are not limited to them.

[0173] [Chemistry 6] In this invention, "R" o With R pThey can bond with each other to form a 5-6 membered ring with 0 to 2 atoms or groups selected from carbon atoms, oxygen atoms, and sulfur atoms (which can be oxidized by 1 or 2 oxygen atoms), and the 5-6 membered ring can be substituted by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 alkoxy, or oxo groups. Examples of such groups are given, but not limited to them.

[0174] [Chemistry 7] (In the above formula, R) n (This means the same as above).

[0175] In this invention, the salt refers to a salt formed by the presence of nitrogen atoms such as hydroxyl, carboxyl, amino, or pyridine rings in the structure of the compound of this invention represented by general formula [I], and is formed by these atoms with a metal or organic base, or with an inorganic acid or organic acid. Examples of metals include alkali metals such as sodium or potassium, or alkaline earth metals such as magnesium or calcium. Examples of organic bases include triethylamine or diisopropylamine. Examples of inorganic acids include phosphoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, boric acid, or sulfuric acid. In addition, examples of organic acids 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, or trifluoromethanesulfonic acid.

[0176] Next, representative examples of compounds comprising 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 thereto. Furthermore, the compound numbers in the tables will also be referred to in the following description.

[0177] Furthermore, representative examples of compounds used as intermediates for manufacturing the nicotinamide derivatives of the present invention are shown in Tables 89 to 104. However, the synthetic intermediates for nicotinamide derivatives are not limited to these. The compound numbers in the tables will also be referenced in the following description.

[0178] Furthermore, the nicotinamide derivatives of the present invention include compounds, for example, having stereoconfigurations of E-isomers and Z-isomers due to the types of substituents bonded to carbon-nitrogen or carbon-carbon double bonds. The present invention includes these E-isomers, Z-isomers, or mixtures containing E-isomers and Z-isomers in any proportion.

[0179] Furthermore, the nicotinamide derivatives of the present invention comprise compounds that have optical isomers due to the presence of one or more chiral carbon atoms and chiral sulfur atoms, and the present invention comprises all optically active, racemic, or diastereomers.

[0180] Furthermore, the nicotinamide derivatives of the present invention comprise compounds that exhibit tautomerism depending on the type of substituents, and the present invention comprises mixtures containing such tautomers in any proportion. Furthermore, the naming of the compounds is not arbitrary; examples include the following groups, but is not limited thereto.

[0181] [Chemistry 8] The following expressions in the tables of this specification, for example as shown below, represent the corresponding groups. 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; CH2F: fluoromethyl; CHF2: difluoromethyl; CF3: trifluoromethyl; CH2CF3: 2,2,2-trifluoro Ethyl; 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: hydroxyl; NO2: nitro; CH2Ph(4-OMe): 4-methoxy-benzyl; Boc: tert-butoxycarbonyl; Npht: 1,3-dioxo-2-yl; [Table 1] [Table 2] [Table 3] [Table 4] [Table 5] [Table 6] [Table 7] [Table 8] [Table 9] [Table 10] [Table 11] [Table 12] [Table 13] [Table 14] [Table 15] [Table 16] [Table 17] [Table 18] [Table 19] [Table 20] [Table 21] [Table 22] [Table 23] [Table 24] [Table 25] [Table 26] [Table 27] [Table 28] [Table 29] [Table 30] [Table 31] [Table 32] [Table 33] [Table 34] [Table 35] [Table 36] [Table 37] [Table 38] [Table 39] [Table 40] [Table 41] [Table 42] [Table 43] [Table 44] [Table 45] [Table 46] [Table 47] [Table 48] [Table 49] [Table 50] [Table 51] [Table 52] [Table 53] [Table 54] [Table 55] [Table 56] [Table 57] [Table 58] [Table 59] [Table 60] [Table 61] [Table 62] [Table 63] [Table 64] [Table 65] [Table 66] [Table 67] [Table 68] [Table 69] [Table 70] [Table 71] [Table 72] [Table 73] [Table 74] [Table 75] [Table 76] [Table 77] [Table 78] [Table 79] [Table 80] [Table 81] [Table 82] [Table 83] [Table 84] [Table 85] [Table 86] [Table 87] [Table 88] [Table 89] [Table 90] [Table 91] [Table 92] [Table 93] [Table 94] [Table 95] [Table 96] [Table 97] [Table 98] [Table 99] [Table 100] [Table 101] [Table 102] [Table 103] [Table 104] On the other hand, the compounds of the present invention represented by general formula [I] can be manufactured according to the manufacturing methods shown below, but are not limited to these methods. Furthermore, hereinafter, for example, "compound represented by general formula [I-1]" and "compound [I-1]" are synonymous (meaning the same).

[0182] In the [Ⅰ], [ⅠⅡ] or [ⅠV] structures described in the manufacturing method, the skeleton of [VI] shown below represents any one of L-1', L-2' or L-3'. [Chemistry 9] (where R is in the formula) 5 R 6 R 7 R 9 R x R y R z A 1 A 2 And Y represents the same meaning as above).

[0183] <Manufacturing Method 1> In the compounds of the present invention, the compound represented by general formula [I-1] can be manufactured using the compound represented by general formula [II-1] according to the method of the reaction formula illustrated below.

[0184] [Chemistry 10] (In the reaction formula, X) 2 Represents halogen atoms, OC(O)OR 10 Detachable groups such as methanesulfonyloxy, trifluoromethanesulfonyloxy, nonafluorobutyryloxy, benzenesulfonyloxy, or p-toluenesulfonyloxy, R 10 Indicates C1~C6 alkyl, R 1 R 2 R 3 R 4 R 7 R 8 R 9 Y and Q represent the same meaning as above.

[0185] That is, the compound represented by general formula [I-1] can be manufactured by the following steps: (Step 1-1) hydrolyzing compound [II-1] in the presence of a suitable acid or base and in a suitable solvent to form compound [II-2], (Step 1-2) forming compound [II-3], an active derivative such as an acyl halide or mixed anhydrides, in a suitable solvent and in the presence or absence of a suitable catalyst, (Step 1-3) reacting it with compound [III-1] in a suitable solvent, in the presence or absence of a suitable base, and in the presence or absence of a suitable catalyst. Furthermore, the compound represented by general formula [I-1] can also be manufactured by the following steps: (Step 1-4) reacting compound [II-2] with compound [III-1] in the presence or absence of a suitable condensing agent and suitable additives, in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base, and in a suitable solvent.

[0186] (Process 1-1) Examples of acids that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, and sulfuric acid; carboxylic acids such as acetic acid and trifluoroacetic acid; and sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid. Furthermore, the amount of acid used should be appropriately selected from the range of 1.0 to 1000 moles relative to 1 mole of compound [II-1], preferably 1.0 to 100 moles.

[0187] 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, magnesium hydroxide, and barium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate; and inorganic bases such as sodium bicarbonate and potassium bicarbonate. Furthermore, the amount of base used should be appropriately selected from 0.1 to 50 moles relative to 1 mole of compound [II-1], preferably 0.5 to 20 moles.

[0188] 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-imidazolinone; alcohols such as methanol, ethanol, and 2-propanol; nitriles such as acetonitrile and propionitrile; ketones such as acetone and methyl ethyl ketone; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [II-1] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0189] The reaction temperature can usually be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 150°C.

[0190] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0191] After the reaction is complete, the reaction mixture is neutralized by adding water, and the precipitated solid is then filtered out or extracted with an organic solvent and concentrated. This process can separate compound [II-2]. The separated compound [II-2] can also be further purified as needed by column chromatography, recrystallization, etc.

[0192] (Process 1-2) Examples of reagents used in this reaction to convert compound [II-2] into compound [II-3] include thionyl chloride, oxalyl chloride, phosphoryl chloride, isobutyl chlorocarbonate, methanesulfonyl chloride, trifluoromethanesulfonyl chloride, and p-toluenesulfonyl chloride. Furthermore, the amount of reagent used to convert compound [II-3] is appropriately selected from the range of 0.5 to 30 moles relative to 1 mole of compound [II-2], and preferably 0.5 to 6.0 moles.

[0193] Examples of catalysts that can be used in this reaction include N,N-dimethylformamide, dimethylacetamide, N-methylpyrrolidone, 1,3-dimethylimidazolinone, tetramethylurea, tetraethylurea, and tetrabutylurea. Furthermore, the amount of catalyst used is appropriately selected from the range of 0.01 to 1.0 moles relative to 1 mole of compound [II-2], and preferably 0.01 to 0.1 moles.

[0194] 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; nitrile hydrocarbons such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [II-2] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0195] The reaction temperature can usually be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 150°C.

[0196] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0197] After the reaction is complete, concentration and other operations are performed to separate compound [II-3].

[0198] (Processes 1-3) The amount of compound [III-1] used in this reaction is usually appropriately selected from the range of 0.5 to 5 moles relative to 1 mole of compound [II-3], preferably 0.5 to 2.5 moles.

[0199] Examples of bases 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-dimethylpyridine; 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 inorganic bases such as sodium bicarbonate and potassium bicarbonate. Furthermore, the amount of base used should be appropriately selected from 1.0 to 20 moles relative to 1 mole of compound [II-3], preferably 1.0 to 10 moles.

[0200] This reaction can be carried out in the presence of a catalyst as needed. Examples of catalysts include tetrabutylammonium bromide, tetrabutylammonium chloride, 15-crown-5, and 18-crown-6. Furthermore, the amount of catalyst used is appropriately selected from the range of 0.001 to 1.0 moles relative to 1 mole of compound [II-3], and preferably 0.01 to 0.1 moles.

[0201] 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; nitrile solvents such as acetonitrile and propionitrile; nonprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [II-3] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0202] The reaction temperature can be selected from any temperature range from -20℃ to the reflux temperature in the reaction system, and preferably it can be carried out in the range of 0℃ to 80℃.

[0203] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 1 minute to 48 hours.

[0204] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [I-1]. The separated compound [I-1] can also be further purified as needed by column chromatography, recrystallization, etc.

[0205] (Processes 1-4) The amount of compound [III-1] used in this reaction may be appropriately selected from the range of 1.0 to 3.0 moles relative to 1 mole of compound [II-2], preferably 1.0 to 1.5 moles.

[0206] 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, and 4-(4,6-dimethoxy-1,3,5-triazine-2-)chloride. Examples of condensing agents include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, {{[(1-cyano-2-ethoxy-2-oxoylethylene)amino]oxy}-4-morpholinylmethylene} dimethylammonium hexafluorophosphate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethylurea-onium hexafluorophosphate, and propylphosphonic anhydride. Furthermore, the amount of condensing agent used relative to 1 mole of compound [II-2] should be appropriately selected from the range of 1.0 to 5.0 moles, preferably 1.0 to 3.0 moles.

[0207] When a catalyst is used in this reaction, examples of usable catalysts include 4-(N,N-dimethylamino)pyridine. Furthermore, the amount of catalyst used should be appropriately selected from the range of 0.001 to 1.0 moles relative to 1 mole of compound [II-2], preferably 0.01 to 0.1 moles.

[0208] When using additives in this reaction, examples of usable additives include 1-hydroxybenzotriazole, N-hydroxysuccinimide, and 1-hydroxy-7-azabenzotriazole. Furthermore, the amount of additive used is appropriately selected from the range of 0.01 to 3.0 moles relative to 1 mole of compound [II-2], and preferably 1.0 to 1.5 moles.

[0209] When a base is used in this reaction, examples of usable bases include triethylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-(N,N-dimethylamino)pyridine, 2,6-dimethylpyridine, and other organic bases. Furthermore, the amount of base used is appropriately selected from 0.1 to 10 moles relative to 1 mole of compound [II-2], preferably 0.1 to 5.0 moles.

[0210] 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; nitrile solvents 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-imidazolinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [II-2] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0211] The reaction temperature can be selected from any temperature range from -20℃ to the reflux temperature in the reaction system, and preferably it can be carried out in the range of 0℃ to 80℃.

[0212] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 120 hours.

[0213] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [I-1]. The separated compound [I-1] can also be further purified as needed by column chromatography, recrystallization, etc.

[0214] <Manufacturing Method 2> The compounds of the present invention, including those represented by general formula [I-2], can also be manufactured according to the following method.

[0215] [Chemistry 11] (where X) 3 R represents a detached group such as a halogen atom, methanesulfonyloxy, trifluoromethanesulfonyloxy, nonafluorobutyryloxy, benzenesulfonyloxy, or p-toluenesulfonyloxy. a R b R 1 R 2R 3 R 4 R 7 R 8 R 9 And Y represents the same meaning as above).

[0216] That is, the compound represented by general formula [I-2] can be produced by reacting compound [IV-1] with compound [V-1] in a suitable solvent, in the presence or absence of a suitable catalyst and a suitable base.

[0217] Regarding the amount of compound [V-1] used in this reaction, if the boiling point of compound [V-1] is less than 40°C, it can be appropriately selected from the range of 5.0 to 1000 moles relative to 1 mole of compound [IV-1], preferably 10 to 600 moles. If the boiling point of compound [V-1] is 40°C or higher, it can be appropriately selected from the range of 1.0 to 20 moles relative to 1 mole of compound [IV-1], preferably 1.0 to 10 moles.

[0218] As catalysts that can be used in this reaction, transition metal complexes or transition metals alone or in combination with ligands can be used. For example, as transition metal complexes, examples include bis(triphenylphosphine)palladium dichloride, tetra(triphenylphosphine)palladium, tris(dibenzylacetone)palladium, and dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium-dichloromethane adduct. Examples of transition metals include 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-bis(dimethylphosphine)propane, 1,2-(bis(diphenylphosphine)ethane), and 1,3-(bis(diphenylphosphine)propane). Furthermore, the amount of metal reagent used may be appropriately selected from the range of 0.001 to 10 moles relative to 1 mole of compound [IV-1], and preferably 0.01 to 5.0 moles.

[0219] 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 sodium carbonate and potassium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; and organic bases such as triethylamine, 4-methylmorpholine, N-ethyldiisopropylamine, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine, 4-N,N-dimethylaminopyridine, and 2,6-dimethylpyridine. Furthermore, the amount of base used relative to 1 mole of compound [IV-1] is 0.1 to 10 moles, preferably 0.1 to 3.0 moles.

[0220] 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 monoglycol dimethyl ether; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; nonprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, 2-propanol, tert-butanol, and methyl cellosolve; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [IV-1] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0221] The reaction temperature can typically be selected from any temperature range from -30°C to the reflux temperature of the reaction system, preferably within the range of 0°C to 150°C. Furthermore, this reaction can also be carried out under microwave irradiation.

[0222] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0223] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [I-2]. The separated compound [I-2] can also be further purified as needed by column chromatography, recrystallization, etc.

[0224] <Manufacturing Method 3> In the compounds of the present invention, the compounds represented by general formula [I-4] can also be manufactured according to the following method.

[0225] [Chemistry 12] (where U)1 Represents a hydrogen atom, dihydroxyboronyl (-B(OH)2) or 4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl, R 11 This indicates C1-C6 alkyl, C3-C8 cycloalkyl, C2-C6 alkenyl, C2-C6 ynyl, tris(C1-C6 alkyl)silylC2-C6 ynyl, and C3-C8 cycloalkylC2-C6 ynyl (the cycloalkyl group can be selected from the substituent group). β Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (substituent with one or more substituents) or 5-12 heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (with one or more substituents in X) 3 R 1 R 2 R 3 R 4 R 7 R 9 Y and Q represent the same meaning as above.

[0226] That is, the compound represented by general formula [I-4] can be produced by reacting compound [I-3] with compound [V-2] in a suitable solvent, in the presence of a suitable catalyst and a suitable base.

[0227] The amount of compound [V-2] used in this reaction is usually appropriately selected from the range of 1.0 to 100 moles relative to 1 mole of compound [I-3], preferably 1.0 to 5.0 moles.

[0228] As catalysts that can be used in this reaction, any transition metal complex or a combination of a transition metal and a ligand can be used. For example, examples of transition metal complexes include bis(triphenylphosphine)palladium dichloride, tetra(triphenylphosphine)palladium, tris(dibenzylacetone)palladium, 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 and N,N-dimethylethylenediamine. Amines, N,N'-dimethylethylenediamine, N,N,N',N'-tetramethylethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, neocouproine, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, 4,5-bis(diphenylphosphine)-9,9-dimethylxanthanium, trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bis(dimethylphosphine)propane, 1,2-bis(diphenylphosphine)ethane, 1,3-bis(diphenylphosphine)propane, 1,1'-bis(diphenylphosphine)ferrocene, etc. Furthermore, the amount of catalyst used may be appropriately selected from the range of 0.001 to 5.0 moles relative to 1 mole of compound [I-3], and preferably 0.01 to 1.0 moles.

[0229] Examples of bases 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-dimethylpyridine; 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 bicarbonate and potassium bicarbonate; 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. Furthermore, the amount of base used relative to 1 mole of compound [I-3] is 0.1 to 10 moles, preferably 0.1 to 5.0 moles.

[0230] 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 monoethylene glycol dimethyl ether; 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-imidazolinone; alcohols such as methanol, ethanol, 2-propanol, tert-butanol, and methyl cellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, methylpyridine, and dimethylpyridine; tertiary amines such as triethylamine and tributylamine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [I-3] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0231] The reaction temperature can be selected from any temperature range from -78°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 180°C.

[0232] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 48 hours.

[0233] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration, thereby separating compound [I-4]. The separated compound [I-4] can also be further purified as needed by column chromatography, recrystallization, etc.

[0234] <Manufacturing Method 4> In the compounds of the present invention, the compounds represented by general formula [I-6] can also be manufactured according to the following method.

[0235] [Chemistry 13] (where U) 2 Represents dihydroxyboronyl (-B(OH)2) or 4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl, R 12 This indicates C2-C6 alkenyl, C2-C6 ynyl, tris(C1-C6 alkyl)silylC2-C6 ynyl, and C3-C8 cycloalkylC2-C6 ynyl (the cycloalkyl group can be selected from the substituent group). β Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (substituent with one or more substituents) or 5-12 heteroaryl groups (the heteroaryl group can be selected from the substituent group) α(with one or more substituents in X) 3 R 1 R 2 R 3 R 4 R 7 R 9 Y and Q represent the same meaning as above.

[0236] That is, the compound represented by general formula [I-6] can be produced by reacting compound [I-5] with compound [V-3] in the presence of a suitable catalyst and a suitable base in a suitable solvent.

[0237] The amount of compound [V-3] used in this reaction is usually appropriately selected from the range of 1.0 to 100 moles relative to 1 mole of compound [I-5], preferably 1.0 to 5.0 moles.

[0238] The catalysts, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as those in manufacturing method 3.

[0239] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration. This process can separate compound [I-6]. The separated compound [I-6] can also be further purified as needed by column chromatography, recrystallization, etc.

[0240] <Manufacturing Method 5> In the compounds of the present invention, the compounds represented by general formula [I-5] can be manufactured using the compounds represented by general formula [I-3] according to the method of the reaction formulas illustrated below.

[0241] [Chemistry 14] (where X) 3 U 2 R 1 R 2 R 3 R 4 R 7 R 9 Y and Q represent the same meaning as above.

[0242] That is, the compound represented by general formula [I-5] can be prepared by reacting compound [I-3] with a boron reagent in a suitable solvent, in the presence or absence of a suitable base, and in the presence or absence of a suitable catalyst.

[0243] The boron reagent used in this reaction is, for example, trimethyl borate, bis(pinacol)diboron, pinacolborane, diboric acid, etc. The amount of boron reagent used in this reaction is usually appropriately selected from the range of 0.5 to 10 moles relative to 1 mole of compound [I-3], preferably 1.0 to 5.0 moles.

[0244] The catalysts, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as those in manufacturing method 3.

[0245] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration. This process can separate compound [I-5]. The separated compound [I-5] can also be further purified as needed by column chromatography, recrystallization, etc.

[0246] <Manufacturing Method 6> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-3], can be manufactured using the compounds represented by general formula [III-2] according to the method of the reaction formulas illustrated below.

[0247] [Chemistry 15] (where R is in the formula) 7 R 8 R 9 And Y represents the same meaning as above).

[0248] That is, the compound represented by general formula [III-3] can be produced by reacting compound [III-2] with a suitable reducing agent in a suitable solvent, in the presence or absence of a suitable acid catalyst, or in the presence or absence of a suitable phase transfer catalyst.

[0249] 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 triethyllithium borohydride; alkali metal salts of dithionite such as sodium dithionite; borane complexes of organo-Lewis bases such as borane-tert-butylamine complexes and borane-dimethyl sulfide complexes; alkali metal salts of aluminum hydrides such as lithium aluminum hydride and sodium bis(2-methoxyethoxy)aluminum hydride; and organo-aluminum hydride compounds such as diisobutylaluminum hydride. Furthermore, the amount of reducing agent used is generally appropriately selected from the range of 0.25 to 50 moles relative to 1 mole of compound [III-2], preferably 0.25 to 50 moles.

[0250] Acid catalysts that can be used in this reaction include, for example, sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid; and carboxylic acids such as formic acid, acetic acid, propionic acid, and trifluoroacetic acid. Furthermore, the amount of acid catalyst used is appropriately selected from the range of 0.01 to 10 moles relative to 1 mole of compound [III-2], and preferably 0.01 to 2.0 moles.

[0251] Phase transfer catalysts that can be used in this reaction include, for example, quaternary ammonium salts such as tetrabutylammonium bromide and tetrabutylammonium chloride. Furthermore, the amount of phase transfer catalyst used is appropriately selected from the range of 0.01 to 10 moles relative to 1 mole of compound [III-2], and preferably 0.01 to 2.0 moles.

[0252] 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 monoethylene glycol dimethyl ether; 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-butanol, and methyl cellosolve; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-2] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0253] The reaction temperature can usually be selected from any temperature range from -78°C to the reflux temperature of the reaction system, and preferably it can be carried out in the range from 0°C to the reflux temperature of the reaction system.

[0254] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0255] After the reaction is complete, the reaction mixture is injected into water, extracted with an organic solvent, and then concentrated to separate compound [III-3]. The separated compound [III-3] can also be further purified as needed by column chromatography, recrystallization, etc.

[0256] <Manufacturing Method 7> Among the intermediates of the compounds of the present invention, the compound represented by general formula [III-3] can be manufactured using the compound represented by general formula [III-4] according to the method of the reaction formulas shown below.

[0257] [Chemistry 16] (where X) 4 R represents a halogen atom. 13 R represents a hydrogen atom or a methoxy group.7 R 8 R 9 And Y represents the same meaning as above).

[0258] That is, the compound represented by general formula [III-3] can be manufactured by the following steps: (Step 7-1) reacting compound [III-4] with a halogenating agent in a suitable solvent, in the presence or absence of a suitable catalyst to form compound [III-5], (Step 7-2) reacting compound [III-5] with benzophenone imine in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base, in a suitable solvent to form compound [III-6], (Step 7-4) 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, in the presence or absence of a suitable catalyst. Alternatively, it can be manufactured by the following steps: (Step 7-3) reacting compound [III-5] with a benzylamine derivative in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base, in a suitable solvent to form compound [III-7], and (Step 7-5) reacting compound [III-7] in the presence or absence of a suitable acid, in the presence or absence of a suitable base, in the presence or absence of a hydrogen atmosphere, in the presence or absence of a suitable catalyst, in a suitable solvent.

[0259] (Process 7-1) Examples of halogenating agents that can be used in this reaction include chlorine, sulfonyl chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, iodine, N-iodosuccinimide, 1,3-diiodo-5,5-dimethylhydantoin, potassium iodate, or mixtures thereof. Furthermore, the amount of halogenating agent used is appropriately selected from 0.01 to 10 moles relative to 1 mole of compound [III-4], preferably 0.02 to 2.0 moles.

[0260] 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; nitrile hydrocarbons such as acetonitrile and propionitrile; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; sulfuric acid; water; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-4] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0261] The reaction temperature can usually be selected from any temperature range from -70°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -20°C to 100°C.

[0262] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0263] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-5]. The separated compound [III-5] can also be further purified as needed by column chromatography, recrystallization, etc.

[0264] (Process 7-2) The amount of benzophenone imine used in this reaction is usually appropriately selected from the range of 1.0 to 100 moles relative to 1 mole of compound [III-5], preferably 1.0 to 5.0 moles.

[0265] As catalysts that can be used in this reaction, transition metal complexes or combinations of transition metals and ligands can be used. Examples of transition metal complexes include bis(triphenylphosphine)palladium dichloride, tetra(triphenylphosphine)palladium, tris(dibenzylacetone)palladium, 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- Dimethyl ethylenediamine, N,N'-dimethyl ethylenediamine, N,N,N',N'-tetramethyl ethylenediamine, 2,2'-bipyridine, 1,10-phenanthroline, new copper reagent, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-diphenyl-1,10-phenanthroline, 4,7-diphenyl-1,10-phenanthroline, 4,5-bis(diphenylphosphine)-9,9-dimethylxanthine, trimethylphosphine, triethylphosphine, tributylphosphine, triphenylphosphine, 1,3-bis(dimethylphosphine)propane, 1,2-bis(diphenylphosphine)ethane, 1,3-bis(diphenylphosphine)propane, 1,1'-bis(diphenylphosphine)ferrocene, etc. Furthermore, the amount of catalyst used may be appropriately selected from the range of 0.001 to 5.0 moles relative to 1 mole of compound [III-5], and preferably 0.01 to 1.0 moles.

[0266] Examples of bases 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-dimethylpyridine; 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 bicarbonate and potassium bicarbonate; 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. Furthermore, the amount of base used relative to 1 mole of compound [III-5] is 0.1 to 10 moles, preferably 0.1 to 5.0 moles.

[0267] 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 monoethylene glycol dimethyl ether; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; nonprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, 2-propanol, tert-butanol, and methyl cellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, methylpyridine, and dimethylpyridine; tertiary amines such as triethylamine and tributylamine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-5] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0268] The reaction temperature can be selected from any temperature range from -78°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 180°C.

[0269] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 48 hours.

[0270] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-6]. The separated compound [III-6] can also be further purified as needed by column chromatography, recrystallization, etc.

[0271] (Process 7-3) The benzylamine derivative used in this reaction can be benzylamine or 4-methoxybenzylamine, etc., and is usually appropriately selected from the range of 1 to 100 moles relative to 1 mole of compound [III-5], preferably 1.0 to 5.0 moles.

[0272] The catalysts, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as in step 7-2.

[0273] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-7]. The separated compound [III-7] can also be further purified as needed by column chromatography, recrystallization, etc.

[0274] (Process 7-4) Compound [III-3], for example, can be prepared 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, in the presence or absence of a hydrogen atmosphere, or in the presence or absence of a suitable catalyst, according to the method described in GREEN' SPROTECTIVE GROUPS in OrganicSynthesis; 5th edition (John Wiley and Sons, 2014, Peter G.M. Wuts).

[0275] After the reaction is complete, insoluble matter is removed by filtration and the filtrate is concentrated, or the reaction mixture is injected into water, extracted with an organic solvent, and then concentrated. These steps allow for the separation of compound [III-3]. The separated compound [III-3] can also be further purified as needed by column chromatography, recrystallization, etc.

[0276] (Process 7-5) Compound [III-3] can be manufactured from compound [III-7] using the same manufacturing method as in step 7-4.

[0277] <Manufacturing Method 8> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-10], can be manufactured using the compounds represented by general formula [III-8] according to the method of the reaction formulas illustrated below.

[0278] [Chemistry 17] (where Y) 2 Represents -C(O)-, -S(O)-, or -S(O)2-, R 14This indicates C1~C6 alkyl, C3~C8 cycloalkyl, C1~C6 alkyl, C1~C6 alkoxy, C1~C6 alkylamino, C1~C 12 Aryl C1~C6 alkyl (the aryl group can be selected from the substituent group) α (one or more substituents in the middle) or C1~C 12 aryl (which can be selected from the substituent group) α (with one or more substituents in X) 3 X 4 R 7 R 9 R i And Y represents the same meaning as above).

[0279] That is, the compound represented by general formula [III-10] can be manufactured by the following steps: (Step 8-1) reacting compound [III-8] with compound [V-4] in a suitable solvent, in the presence or absence of a suitable catalyst, and in the presence or absence of a suitable base to form compound [III-9], and (Step 8-2) reacting compound [III-9] with compound [V-5] in the presence or absence of a suitable base, in the presence or absence of a suitable catalyst, and in a suitable solvent.

[0280] (Process 8-1) The amount of compound [V-4] used in this reaction is usually appropriately selected from the range of 1.0 to 5.0 moles relative to 1 mole of compound [III-8], and preferably 1.0 to 2.5 moles.

[0281] Examples of bases 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-dimethylpyridine; 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 inorganic bases such as sodium bicarbonate and potassium bicarbonate. Furthermore, the amount of base used should be appropriately selected from 1.0 to 20 moles relative to 1 mole of compound [III-8], preferably 1.0 to 10 moles.

[0282] This reaction can be carried out in the presence of a catalyst if necessary. Examples of catalysts include tetrabutylammonium bromide, tetrabutylammonium chloride, 15-crown-5, and 18-crown-6. Furthermore, the amount of catalyst used can be appropriately selected from 0.001 to 1 mole relative to 1 mole of compound [III-8], and is preferably 0.01 to 0.1 moles.

[0283] 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; nitrile solvents such as acetonitrile and propionitrile; nonprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-8] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0284] The reaction temperature can be selected from any temperature range from -20℃ to the reflux temperature in the reaction system, and preferably it can be carried out in the range of 0℃ to 80℃.

[0285] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 1 minute to 48 hours.

[0286] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration, thereby separating compound [III-9]. The separated compound [III-9] can also be further purified by column chromatography or other methods as needed.

[0287] (Process 8-2) The amount of compound [V-5] used in this reaction is usually appropriately selected from the range of 1.0 to 20 moles relative to 1 mole of compound [III-9], preferably 1.0 to 3.0 moles.

[0288] 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 bicarbonate and potassium bicarbonate; 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-dimethylpyridine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. Furthermore, the amount of base used should be appropriately selected from 0.5 to 10 moles relative to 1 mole of compound [III-9], preferably 1.0 to 5.0 moles.

[0289] Examples of catalysts that can be used in this reaction include alkali metal iodides such as sodium iodide and potassium iodide. Furthermore, the amount of catalyst used should be appropriately selected from 0.01 to 0.5 moles relative to 1 mole of compound [III-9], preferably 0.01 to 0.1 moles.

[0290] 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 monoethylene glycol dimethyl ether; 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-imidazolinone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, methylpyridine, and dimethylpyridine; tertiary amines such as triethylamine and tributylamine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-9] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0291] The reaction temperature can usually be selected from any temperature range from -78°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 100°C.

[0292] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0293] After the reaction is complete, the reaction mixture is injected into water, extracted with an organic solvent, and then concentrated to separate compound [III-10]. The separated compound [III-10] can also be further purified as needed by column chromatography, recrystallization, etc.

[0294] <Manufacturing Method 9> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-14], can be manufactured using the compounds represented by general formula [III-11] according to the method of the reaction formulas illustrated below.

[0295] [Chemistry 18] (In the formula, K represents a 3- to 6-membered carbon ring, R) 15 Represents cyano or C1~C6 alkoxycarbonyl, R 7 R 9And Y represents the same meaning as above).

[0296] That is, the compound represented by general formula [III-14] can be manufactured by the following steps: (Step 9-1) reacting compound [III-11] with compound [V-6] in the presence or absence of a suitable base, in the presence or absence of a suitable catalyst, and in a suitable solvent to form compound [III-12], (Step 9-2) nitrifying the compound represented by general formula [III-12] to form compound [III-13], and (Step 9-3) hydrolyzing compound [III-13] in the presence of a suitable acid or base and in a suitable solvent.

[0297] (Process 9-1) Examples of compounds [V-6] used in this reaction include 1,2-dibromoethane, 1,2-diiodoethane, 1,3-dibromopropane, 1,4-dibromobutane, 1,5-dibromopentane, and ethylene carbonate. Furthermore, the amount of compound [V-6] used is appropriately selected from 1.0 to equimolar of the solvent amount relative to 1 mole of compound [III-11], and preferably 1.0 to 20 moles.

[0298] 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 bicarbonate and potassium bicarbonate; 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-dimethylpyridine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. Furthermore, the amount of base used should be appropriately selected from 0.5 to 20 moles relative to 1 mole of compound [III-11], preferably 1.0 to 10 moles.

[0299] Examples of catalysts that can be used in this reaction include alkali metal iodides such as sodium iodide and potassium iodide. Furthermore, the amount of catalyst used is appropriately selected from the range of 0.01 to 0.5 moles relative to 1 mole of compound [III-11], and preferably 0.01 to 0.1 moles.

[0300] 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 monoethylene glycol dimethyl ether; 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-imidazolinone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, methylpyridine, and dimethylpyridine; tertiary amines such as triethylamine and tributylamine; water or mixtures thereof. Furthermore, the amount of solvent used is 0.1 to 1000 liters relative to 1 mole of compound [III-11], preferably 0.2 to 100 liters.

[0301] The reaction temperature can usually be selected from any temperature range from -78°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 100°C.

[0302] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0303] After the reaction is complete, the reaction mixture is injected into water, extracted with an organic solvent, and then concentrated to separate compound [III-12]. The separated compound [III-12] can also be further purified as needed by column chromatography, recrystallization, etc.

[0304] (Process 9-2) The compound represented by general formula [III-13] can be prepared by nitrifying the compound represented by general formula [III-12] according to the method described in the "Nitro and Nitrosium Compounds" section of the 4th edition (Maruzen), Volume 20 of "Lectures on Experimental Chemistry".

[0305] Compound [III-13] can also be further purified as needed by column chromatography, recrystallization, etc.

[0306] (Process 9-3) The acids, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as in step 1-1.

[0307] After the reaction is complete, the reaction mixture is neutralized by adding water, and the precipitated solid is filtered out. Alternatively, it can be extracted with an organic solvent and then concentrated to separate compound [III-14]. The separated compound [III-14] can also be further purified as needed by column chromatography, recrystallization, etc.

[0308] <Manufacturing Method 10> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-18], can be manufactured using the compounds represented by general formula [III-15] according to the method of the reaction formulas illustrated below.

[0309] [Chemistry 19] (where Z) 2 Represents hydrogen atom, halogen atom, nitro group, R 16 This indicates C1-C6 alkyl or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β (substituents in C2-C6), C2-C6 alkenyl, C2-C6 ynyl, C6-C 12 aryl (which can be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (Substitution of one or more substituents) or 3- to 6-membered heterocyclic groups (the heterocyclic group can be selected from the substituent group) α (with one or more substituents in R) 17 X represents a hydrogen atom or a C1-C6 alkyl group. 2 X 4 R 7 R 9 And Y represents the same meaning as above).

[0310] That is, the compound represented by general formula [III-18] can be manufactured by the following steps: (Step 10-1) after forming compound [III-15] into an active derivative such as an acyl halide or mixed anhydride, i.e., compound [III-16], in a suitable solvent, in the presence or absence of a suitable catalyst, or in the absence of a suitable catalyst, (Step 10-2) after reacting it with a methoxyamine in a suitable solvent, in the presence or absence of a suitable base, or in the presence or absence of a suitable catalyst, to form compound [III-17], (Step 10-4) after reacting compound [III-17] with a Grignard reagent or lithium reagent represented by compound [V-7] in the presence or absence of a suitable additive, in a suitable solvent. Alternatively, it can be manufactured by the following steps: (Step 10-3) reacting compound [III-15] with methoxyamines in the presence or absence of a suitable condensing agent and suitable additives, in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base, and in a suitable solvent to form compound [III-17], followed by step 10-4.

[0311] (Process 10-1) The reagents, acids, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction to convert compound [III-15] into compound [III-16] are the same as in steps 1-2.

[0312] After the reaction is complete, concentration and other operations are performed to separate compound [III-16].

[0313] (Process 10-2) Methoxyamines that can be used in this reaction include, for example, methoxyamine, methoxyamine hydrochloride, methoxyamine sulfate, and N,O-dimethylhydroxyamine hydrochloride. Furthermore, the amount of methoxyamine used is typically selected from the range of 1.0 to 5.0 moles relative to 1 mole of compound [III-16], and preferably 1.0 to 2.5 moles.

[0314] The base, solvent, reaction temperature, and reaction time that can be used in this reaction are the same as in steps 1-3.

[0315] After the reaction is complete, the reaction mixture is injected into water, the precipitated solid is filtered out, or it is extracted with an organic solvent and then concentrated, thereby separating compound [III-17].

[0316] (Process 10-3) Methoxyamines that can be used in this reaction include, for example, methoxyamine, methoxyamine hydrochloride, and methoxyamine sulfate. Furthermore, the amount of methoxyamine used is appropriately selected from the range of 1.0 to 3.0 moles relative to 1 mole of compound [III-15], preferably 1.0 to 1.5 moles.

[0317] The condensing agents, additives, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as in steps 1-4.

[0318] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-17]. The separated compound [III-17] can also be further purified as needed by column chromatography, recrystallization, etc.

[0319] (Process 10-4) The amount of compound [V-7] used in this reaction is usually appropriately selected from the range of 1.0 to 10 moles relative to 1 mole of compound [III-17], preferably 1.0 to 4.0 moles.

[0320] Examples of additives that can be used in this reaction include N,N,N',N'-tetramethylethylenediamine, hexamethylphosphoramide, and N,N'-dimethylacrylurea. Furthermore, the amount of additive used relative to 1 mole of compound [III-17] is 1.0 to 10 moles, preferably 1.0 to 3.0 moles.

[0321] 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 monoethylene glycol dimethyl ether; 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-imidazolinone; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane, or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-17] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0322] The reaction temperature can usually be selected from any temperature range from -78°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -78°C to 70°C.

[0323] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0324] Compound [III-18] can be separated by concentration and other operations. The separated compound [III-18] can also be further purified as needed by column chromatography, recrystallization, etc.

[0325] <Manufacturing Method 11> The intermediates of the compounds of the present invention, the compounds represented by general formulas [III-20] and [III-21], can be manufactured using the compound represented by general formula [III-18] according to the method of the reaction formulas illustrated below.

[0326] [Chemistry 20] (where R is in the formula) 18 This indicates C1-C6 alkyl or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (substituents in the group), C1~C6 alkoxy-C1~C6 alkyl, C1~C6 alkyl carbonyl or C3~C8 cycloalkyl carbonyl (the cycloalkyl group can be selected from the substituent group) β(substituents in Z) 2 X 3 X 4 R 7 R 9 R 16 And Y represents the same meaning as above).

[0327] That is, the compound represented by general formula [III-20] can be manufactured by the following steps: (Step 11-1) reacting the compound represented by compound [III-18] with a suitable reducing agent in a suitable solvent to form compound [III-19], and (Step 11-2) reacting compound [III-19] with compound [V-8] in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base, and in a suitable solvent. Furthermore, the compound represented by general formula [III-21] can be manufactured by the following steps: (Step 11-3) reacting 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.

[0328] (Process 11-1) Examples of reducing agents that can be used in this reaction include alkali metal salts of borohydrides such as sodium borohydride, lithium borohydride, and triethyllithium borohydride; borane complexes of organo-Lewis bases such as borane-tert-butylamine complexes and borane-dimethyl sulfide complexes; alkali metal salts of aluminum hydrides such as lithium aluminum hydride and sodium bis(2-methoxyethoxy)aluminum hydride; and organo-aluminum hydride compounds such as diisobutylaluminum hydride. Furthermore, the amount of reducing agent used should be appropriately selected from the range of 0.25 to 5.0 moles relative to 1 mole of compound [III-18], preferably 0.25 to 2.0 moles.

[0329] 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 monoethylene glycol dimethyl ether; 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 mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-18] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0330] The reaction temperature can be selected from any temperature range from -78°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10°C to 60°C.

[0331] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0332] Compound [III-19] can be separated by injecting the reaction mixture into water, filtering to remove the precipitated solid, or by extraction with an organic solvent followed by concentration. The separated compound [III-19] can also be further purified as needed by column chromatography, recrystallization, etc.

[0333] (Process 11-2) The amount of compound [V-8] used in this reaction may be appropriately selected from the range of 1.0 to 15 moles relative to 1 mole of compound [III-19], preferably 1.0 to 6.0 moles.

[0334] Examples of bases that can be used in this reaction include alkali metal hydroxides such as 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 bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; or 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-dimethylpyridine. Furthermore, the amount of base used should be appropriately selected from 1.0 to 5.0 moles relative to 1 mole of compound [III-19], preferably 1.0 to 1.5 moles.

[0335] Examples of catalysts that can be used in this reaction include tetrabutylammonium bromide and tetrabutylammonium iodide. Furthermore, the amount of catalyst used is appropriately selected from the range of 0.01 to 1.0 moles relative to 1 mole of compound [III-19], and preferably 0.05 to 0.5 moles.

[0336] 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-imidazolinone; 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 methylpyridine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-19] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0337] The reaction temperature can usually be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 150°C.

[0338] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 48 hours.

[0339] Compound [III-20] can be separated by injecting the reaction mixture into water, filtering to remove the precipitated solid, or by extraction with an organic solvent followed by concentration. The separated compound [III-20] can also be further purified as needed by column chromatography, recrystallization, etc.

[0340] (Process 11-3) Examples of halogenating agents that can be used in this reaction include hydrohalogenated acids such as hydrochloric acid and hydrobromic acid; alkali metal halogenated compounds such as lithium chloride and sodium bromide; thionyl chloride, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphoryl chloride, hexachloroacetone, carbon tetrachloride, and carbon tetrabromide. Furthermore, the amount of halogenating agent used in this reaction is appropriately selected from 0.5 to 30 moles relative to 1 mole of compound [III-19], preferably 0.5 to 4.0 moles.

[0341] Examples of catalysts that can be used in this reaction include N,N-dimethylformamide and zinc chloride. Furthermore, the amount of catalyst used is appropriately selected from 0.01 to 10 moles relative to 1 mole of compound [III-19], preferably 0.01 to 1.0 moles.

[0342] When an additive is used in this reaction, examples of usable additives include triphenylphosphine, tributylphosphine, and sulfuric acid. Furthermore, the amount of additive used should be appropriately selected from the range of 0.01 to 3.0 moles relative to 1 mole of compound [III-19], preferably 1.0 to 1.5 moles.

[0343] Examples of bases 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, and 2,6-dimethylpyridine. Furthermore, the amount of base used is appropriately selected from 1.0 to 20 moles relative to 1 mole of compound [III-19], preferably 1.0 to 5.0 moles.

[0344] 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; nitrile hydrocarbons such as acetonitrile and propionitrile; esters such as ethyl acetate, butyl acetate, and ethyl propionate; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-19] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0345] The reaction temperature can usually be selected from any temperature range from -40°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -20°C to 120°C.

[0346] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0347] Compound [III-21] can be separated by injecting the reaction mixture into water, filtering to remove the precipitated solid, or by extraction with an organic solvent followed by concentration. The separated compound [III-21] can also be further purified as needed by column chromatography, recrystallization, etc.

[0348] <Manufacturing Method 12> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-22], can be manufactured using the compounds represented by general formula [III-18] according to the method of the reaction formulas illustrated below.

[0349] [Chemistry 21] (where R is in the formula) 19This indicates C1-C6 alkyl or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β Substituents in the group (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C8 cycloalkyl-C2-C6 ynyl (the cycloalkyl group can be selected from the substituent group)). β Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (substituent with one or more substituents) or 5-12 heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (with more than one substituent in Z) 2 X 4 R 7 R 9 R 16 And Y represents the same meaning as above).

[0350] That is, the compound represented by general formula [III-22] can be produced by reacting compound [III-18] with compound [V-9] in the presence or absence of a suitable additive in a suitable solvent.

[0351] The amount of compound [V-9] used in this reaction may be appropriately selected from the range of 1.0 to 10 moles relative to 1 mole of compound [III-18], preferably 1.0 to 5.0 moles.

[0352] Examples of additives that can be used in this reaction include N,N,N',N'-tetramethylethylenediamine, hexamethylphosphoramide, and N,N'-dimethylacrylurea. Furthermore, the amount of additive used relative to 1 mole of compound [III-18] is 1.0 to 10 moles, preferably 1.0 to 3.0 moles.

[0353] 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 monoethylene glycol dimethyl ether; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-18] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0354] The reaction temperature can usually be selected from any temperature range from -80°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -80°C to 100°C.

[0355] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 36 hours.

[0356] After the reaction is complete, the reaction mixture is injected into water, etc., and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-22]. The separated compound [III-22] can also be further purified as needed by column chromatography, recrystallization, etc.

[0357] <Manufacturing Method 13> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-26], can be manufactured using the compounds represented by general formula [III-23] according to the method of the reaction formulas illustrated below.

[0358] [Chemistry 22] (where R is in the formula) 20 Indicates C6~C 12 aryl (which can be selected from the substituent group) α (substituent with one or more substituents) or 5-12 heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (with more than one substituent in Z) 2 X 4 R 7 R 9 And Y represents the same meaning as above).

[0359] That is, the compound represented by general formula [III-26] can be manufactured by the following steps: (Step 13-1) reacting compound [III-23] with compound [V-10] in a suitable solvent to form compound [III-24], (Step 13-2) forming compound [III-25] from compound [III-24] by a dehydration reaction, and (Step 13-3) the Simmons-Smith reaction of compound [III-25].

[0360] (Process 13-1) Compound [III-24] can be manufactured using the same method as manufacturing method 12.

[0361] (Process 13-2) The compound represented by general formula [III-25] can be prepared by dehydrating the compound represented by general formula [III-24] according to the method described in the "Hydrocarbons" section of the 4th edition (Maruzen), Volume 19 of "Lectures on Experimental Chemistry".

[0362] Compound [III-25] can also be further purified as needed by column chromatography, recrystallization, etc.

[0363] (Process 13-3) The compound represented by general formula [III-26] can be prepared by the Simons-Smith reaction of the compound represented by general formula [III-25] according to the method described in the "Synthesis of Group 12 Organometallic Compounds" section of the 4th edition of "Lectures on Experimental Chemistry" (Maruzen), Volume 25.

[0364] Compound [III-26] can also be further purified as needed by column chromatography, recrystallization, etc.

[0365] <Manufacturing Method 14> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-27], can be manufactured using the compounds represented by general formula [III-21] according to the method of the reaction formulas illustrated below.

[0366] [Chemistry 23] (where R is in the formula) 21 This indicates C1-C6 alkyl or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β Substituents in the group (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkoxy, C1-C6 alkyl, C3-C8 cycloalkyl, C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group)). β Substituents in (C6~C) 12 aryl (which can be selected from the substituent group) α (substituent with one or more substituents) or 5-12 heteroaryl groups (the heteroaryl group can be selected from the substituent group) α (with one or more substituents in A) 3 Represents oxygen atom, sulfur atom, -NH, Z 2 X 4 R 7 R 9 R 16 And Y represents the same meaning as above).

[0367] That is, the compound represented by general formula [III-27] can be produced by reacting compound [III-21] with compound [V-11] in the presence of a suitable base, in the presence or absence of a suitable catalyst, and in a suitable solvent.

[0368] The amount of compound [V-11] used in this reaction is usually appropriately selected from the range of 1.0 to 5.0 moles relative to 1 mole of compound [III-21], preferably 1.0 to 4.0 moles.

[0369] 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 bicarbonate and potassium bicarbonate; 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-dimethylpyridine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. Furthermore, the amount of base used should be appropriately selected from 0.5 to 20 moles relative to 1 mole of compound [III-21], preferably 1.0 to 5.0 moles.

[0370] Examples of catalysts that can be used in this reaction include alkali metal iodides such as sodium iodide and potassium iodide. Furthermore, the amount of catalyst used is appropriately selected from the range of 0.01 to 0.5 moles relative to 1 mole of compound [III-21], and preferably 0.01 to 0.1 moles.

[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 monoethylene glycol dimethyl ether; 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-imidazolinone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, methylpyridine, and dimethylpyridine; tertiary amines such as triethylamine and tributylamine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-21] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0372] The reaction temperature can usually be selected from any temperature range from -78°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -20°C to 100°C.

[0373] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0374] After the reaction is complete, the reaction mixture is injected into water, extracted with an organic solvent, and then concentrated to separate compound [III-27]. The separated compound [III-27] can also be further purified as needed by column chromatography, recrystallization, etc.

[0375] <Manufacturing Method 15> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-30], can be manufactured using the compounds represented by general formula [III-21] according to the method of the reaction formulas illustrated below.

[0376] [Chemistry 24] (where R is in the formula) 22 This indicates C1-C6 alkyl or C3-C8 cycloalkyl (the cycloalkyl group can be selected from the substituent group). β Substituents in (C1-C6 haloalkyl, C3-C8 cycloalkyl, C1-C6 alkyl (the cycloalkyl group can be selected from the substituent group) β (Substituents in the group) or C1~C6 alkoxy C1~C6 alkyl, Z 2 X 3 X 4 R 7 R 9 R 16 And Y represents the same meaning as above).

[0377] That is, the compound represented by general formula [III-30] can be manufactured by the following steps: (Step 15-1) reacting compound [III-21] with thioacetate in a suitable solvent to form compound [III-28], (Step 15-2) reacting compound [III-28] in the presence of a suitable acid or base or a suitable reducing agent in a suitable solvent to form compound [III-29], (Step 15-3) reacting compound [III-29] with compound [V-12] in the presence or absence of a suitable base, in the presence or absence of a suitable free radical initiator in a suitable solvent.

[0378] (Process 15-1) Examples of thioacetic acid salts that can be used in this reaction include sodium thioacetate and potassium thioacetate. Furthermore, the amount of thioacetic acid salt used should be appropriately selected from the range of 1.0 to 5.0 moles relative to 1 mole of compound [III-21], preferably 1.0 to 3.5 moles.

[0379] 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; nitrile solvents such as acetonitrile and propionitrile; nonprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolinone; 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 mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-21] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0380] The reaction temperature can usually be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10°C to 40°C.

[0381] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0382] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-28]. The separated compound [III-28] can also be further purified as needed by column chromatography, recrystallization, etc.

[0383] (Process 15-2) Examples of acids that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, or sulfuric acid; carboxylic acids such as acetic acid, propionic acid, and trifluoroacetic acid; and sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid. Furthermore, the amount of acid used should be appropriately selected from 1.0 to equimolar amounts relative to 1 mole of compound [III-28], preferably 1.0 to 100 moles.

[0384] 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 sodium carbonate and potassium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydrides such as sodium hydride and potassium hydride; and metal salts of alcohols such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. Furthermore, the amount of base used is appropriately selected from 0.1 to 50 moles relative to 1 mole of compound [III-28], preferably 0.5 to 20 moles.

[0385] Examples of reducing agents that can be used in this reaction include sodium borohydride, lithium aluminum hydride, diisobutylaluminum hydride, and sodium bis(2-methoxyethoxy)aluminum hydride. Furthermore, the amount of reducing agent used should be appropriately selected from the range of 1.0 to 5.0 moles relative to 1 mole of compound [III-28], preferably 1.0 to 2.5 moles.

[0386] 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; nitrile solvents such as acetonitrile and propionitrile; nonprotic polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane, and 1,3-dimethyl-2-imidazolinone; 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 mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-28] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0387] The reaction temperature can usually be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10°C to 40°C.

[0388] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0389] After the reaction is complete, the reaction mixture is neutralized by adding water, and the precipitated solid is then filtered out or extracted with an organic solvent and concentrated. This process can separate compound [III-29]. The separated compound [III-29] can also be further purified as needed by column chromatography, recrystallization, etc.

[0390] (Process 15-3) The amount of compound [V-12] used in this reaction may be appropriately selected from 1.0 to 100 moles relative to 1 mole of compound [III-29], preferably 1.0 to 3.5 moles.

[0391] 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 sodium carbonate and potassium carbonate; inorganic bases such as alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; 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. Furthermore, the amount of base used should be appropriately selected from 1.0 to 5.0 moles relative to 1 mole of compound [III-29], preferably 1.0 to 3.0 moles.

[0392] Free radical initiators that can be used in this reaction include, for example, sulfurous acid, sulfites, and sulfurous acid adducts such as Rongalite (trade name: sodium formaldehyde sulfoxylate). Furthermore, the amount of free radical initiator used should be appropriately selected from the range of 0.01 to 5.0 moles relative to 1 mole of compound [III-29], preferably 0.01 to 1.5 moles.

[0393] 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-imidazolinone; 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 methylpyridine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-29] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0394] The reaction temperature can be selected from any temperature range from -30℃ to the reflux temperature in the reaction system, and preferably it can be carried out in the range of 0℃ to 150℃.

[0395] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 24 hours.

[0396] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-30]. The separated compound [III-30] can also be further purified as needed by column chromatography, recrystallization, etc.

[0397] <Manufacturing Method 16> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-33], can be manufactured using the compounds represented by general formula [III-14] according to the method of the reaction formulas illustrated below.

[0398] [Chemistry 25] (where K and X are in the formula) 4 R 7 R 9 And Y represents the same meaning as above).

[0399] That is, the compound represented by general formula [III-33] can be manufactured by the following steps: (Step 16-1) reacting compound [III-14] in the presence of a suitable reducing agent and in a suitable solvent to form compound [III-31], (Step 16-2) reacting compound [III-31] in the presence of a suitable halogenating agent and in a suitable solvent to form compound [III-32], (Step 16-3) reacting compound [III-32] with a cyaniding agent in the presence or absence of a suitable base and in a suitable solvent.

[0400] (Process 16-1) The compound represented by general formula [III-31] can be prepared by reducing the compound represented by general formula [III-14] according to the method described in the "Common Reduction Section" of the 4th edition (Maruzen), Volume 26 of "Lectures on Experimental Chemistry".

[0401] Compound [III-31] can also be further purified as needed by column chromatography, recrystallization, etc.

[0402] (Process 16-2) The halogenating agent used in this reaction, as well as the amount of halogenating agent used, the catalysts, additives, bases, solvents, reaction temperature, and reaction time, are the same as in step 11-3.

[0403] Compound [III-32] can be separated by injecting the reaction mixture into water, filtering to remove the precipitated solid, or by extraction with an organic solvent followed by concentration. The separated compound [III-32] can also be further purified as needed by column chromatography, recrystallization, etc.

[0404] (Process 16-3) Examples of cyaniding agents used in this reaction include sodium cyanide, potassium cyanide, ammonium cyanide, zinc cyanide, copper cyanide, or mixtures thereof. Furthermore, the amount of cyanide compound used is typically selected from the range of 1.0 to 100 moles relative to 1 mole of compound [III-32], preferably 1.0 to 5.0 moles.

[0405] 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-imidazolinone; 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 methylpyridine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-32] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0406] The reaction temperature can generally be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 150°C.

[0407] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0408] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration, thereby separating compound [III-33]. The separated compound [III-33] can also be further purified as needed by column chromatography, recrystallization, etc.

[0409] <Manufacturing Method 17> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-36], can be manufactured using the compounds represented by general formula [III-15] according to the method of the reaction formulas illustrated below.

[0410] [Chemistry 26] (where Z) 2 X 3 X 4 R 7 R 9 R 10 R 18 And Y represents the same meaning as above).

[0411] That is, the compound represented by general formula [III-36] can be manufactured by the following steps: (Step 17-1) after forming compound [III-34] by esterification of compound [III-15], (Step 17-2) after forming compound [III-35] by reacting tetraalkyl titanate and ethyl magnesium halide with compound [III-34] in a suitable solvent, (Step 17-3) after reacting compound [III-35] with compound [V-8] in a suitable solvent in the presence or absence of a suitable base.

[0412] (Process 17-1) The compound represented by general formula [III-34] can be prepared by esterifying the compound represented by general formula [III-15] according to the method described in the "Carboxylic Acids and Derivatives" section of the 4th edition of "Lectures on Experimental Chemistry" (Maruzen), Volume 22.

[0413] Compound [III-34] can also be further purified as needed by column chromatography, recrystallization, etc.

[0414] (Process 17-2) Examples of tetraalkyl orthotitanate esters used in this reaction include tetraethyl orthotitanate, tetraisopropyl orthotitanate, tetrabutyl orthotitanate, tetraisobutyl orthotitanate, and tetra(2-ethylhexyl) orthotitanate. Furthermore, the amount of tetraalkyl orthotitanate ester used is typically selected from 1.0 to 10 moles relative to 1 mole of compound [III-34], and preferably 1.0 to 3.0 moles.

[0415] Examples of ethyl magnesium halides used in this reaction include ethyl magnesium chloride, ethyl magnesium bromide, and ethyl magnesium iodide. Furthermore, the amount of ethyl magnesium halide used is typically selected from the range of 1.0 to 10 moles relative to 1 mole of compound [III-34], and preferably from 1.0 to 5.0 moles.

[0416] 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; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-34] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0417] The reaction temperature can usually be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 100°C.

[0418] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0419] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration, thereby separating compound [III-35]. The separated compound [III-35] can also be further purified as needed by column chromatography, recrystallization, etc.

[0420] (Process 17-3) The amount of compound [V-8] used in this reaction may be appropriately selected from the range of 1.0 to 100 moles relative to 1 mole of compound [III-35], preferably 1.0 to 3.5 moles.

[0421] Examples of bases 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-dimethylpyridine; 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 bicarbonate and potassium bicarbonate; 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. Furthermore, the amount of base used relative to 1 mole of compound [III-35] is 0.1 to 10 moles, preferably 0.1 to 5.0 moles.

[0422] 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 monoethylene glycol dimethyl ether; 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-imidazolinone; alcohols such as methanol, ethanol, 2-propanol, tert-butanol, and methyl cellosolve; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, methylpyridine, and dimethylpyridine; tertiary amines such as triethylamine and tributylamine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-35] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0423] The reaction temperature can be selected from any temperature range from -30℃ to the reflux temperature in the reaction system, and preferably can be carried out in the range of -10℃ to 150℃.

[0424] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and is typically 10 minutes to 48 hours.

[0425] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration, thereby separating compound [III-36]. The separated compound [III-36] can also be further purified as needed by column chromatography, recrystallization, etc.

[0426] <Manufacturing Method 18> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-38], can be manufactured using the compounds represented by general formula [III-14] according to the method of the reaction formulas illustrated below.

[0427] [Chemistry 27] (where K and R are in the formula) 7 R 9 R 10 And Y represents the same meaning as above).

[0428] That is, the compound represented by general formula [III-38] can be manufactured by the following steps: (step 18-1) by reacting compound [III-14] with diphenyl azidophosphate (DPPA) in a suitable solvent and in the presence of a suitable base to produce compound [III-37], and (step 18-2) by reacting compound [V-13] with compound [III-37].

[0429] (Process 18-1) The amount of DPPA that can be used in this reaction can be appropriately selected from the range of 1.0 to 5.0 moles relative to 1 mole of compound [III-14], preferably 1.0 to 2.5 moles.

[0430] Examples of bases 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 inorganic bases such as sodium bicarbonate and potassium bicarbonate. Furthermore, the amount of base used should be appropriately selected from 1.0 to 5.0 moles relative to 1 mole of compound [III-14], preferably 1.0 to 2.5 moles.

[0431] 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-imidazolinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-14] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0432] (Process 18-2) Examples of compounds [V-13] that can be used in this reaction include methanol, ethanol, 2-propanol, tert-butanol, and other alcohols. Furthermore, the amount of compound [V-13] used is appropriately selected from 1.0 to equimolar amounts relative to 1 mole of compound [III-37], preferably 1.0 to 100 moles.

[0433] The reaction temperature can be selected from any temperature range from -20°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 120°C.

[0434] The reaction time varies depending on the reaction temperature, the substrate, and the amount of reaction, and typically ranges from 1 minute to 48 hours.

[0435] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration, thereby separating compound [III-38]. The separated compound [III-38] can also be further purified as needed by column chromatography, recrystallization, etc.

[0436] <Manufacturing Method 19> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-40], can be manufactured using the compounds represented by general formula [III-39] according to the method of the reaction formulas illustrated below.

[0437] [Chemistry 28] (where R is in the formula) i R k Z 2 X 4 R 7 R 9 And Y represents the same meaning as above).

[0438] That is, the compound represented by general formula [III-40] can be produced by reacting compound [III-39] with compound [V-14] in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base, and in a suitable solvent.

[0439] The amount of compound [V-14] used in this reaction is usually appropriately selected from the range of 1.0 to 100 moles relative to 1 mole of compound [III-39], preferably 1.0 to 10 moles.

[0440] The catalysts, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as in step 7-2.

[0441] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-40]. The separated compound [III-40] can also be further purified as needed by column chromatography, recrystallization, etc.

[0442] <Manufacturing Method 20> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-3], can be manufactured using the compounds represented by general formula [III-41] according to the method of the reaction formulas illustrated below.

[0443] [Chemistry 29] (where R is in the formula) 7 R 8 R 9 R 10 And Y represents the same meaning as above).

[0444] That is, the compound represented by general formula [III-3] can be manufactured by the following steps: (Step 20-1) by hydrolyzing compound [III-41] in a suitable solvent in the presence of a suitable base or a suitable acid to form compound [III-42], (Step 20-2) by the Curtiss rearrangement reaction of compound [III-42] followed by treatment based on compound [V-13] to form compound [III-43], (Step 20-3) by reacting compound [III-43] in the presence or absence of a suitable acid, in the presence or absence of a suitable base, in the presence or absence of a suitable catalyst, or in a suitable solvent.

[0445] (Process 20-1) Examples of bases that can be used in this reaction include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, and barium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; and inorganic bases such as sodium bicarbonate and potassium bicarbonate. Furthermore, the amount of base used should be appropriately selected from 0.1 to 50 moles relative to 1 mole of compound [III-41], preferably 0.5 to 20 moles.

[0446] Examples of acids that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, or sulfuric acid; and carboxylic acids such as acetic acid or trifluoroacetic acid. Furthermore, the amount of acid used should be appropriately selected from the range of 1.0 to 1000 moles relative to 1 mole of compound [III-41], preferably 1.0 to 100 moles.

[0447] 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 mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-41] is 0.1 to 500 liters, preferably 0.3 to 30 liters.

[0448] The reaction temperature can usually be selected from any temperature range from -30°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 150°C.

[0449] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0450] After the reaction is complete, the reaction mixture is neutralized by adding water, and the precipitated solid is then filtered out or extracted with an organic solvent and concentrated. This process can separate compound [III-42]. The separated compound [III-42] can also be further purified as needed by column chromatography, recrystallization, etc.

[0451] (Process 20-2) Compound [III-43] can be manufactured from compound [III-42] using the same method as manufacturing method 18.

[0452] Compound [III-43] can be separated by injecting the reaction mixture into water, filtering to remove the precipitated solid, or by extraction with an organic solvent followed by concentration. The separated compound [III-43] can also be further purified as needed by column chromatography, recrystallization, etc.

[0453] (Process 20-3) Compound [III-3], for example, can be prepared 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, in the presence or absence of a suitable catalyst, according to the method described in GREEN'S PROTECTIVE GROUPS in OrganicSynthesis; 5th Edition (John Wiley and Sons, 2014, Peter GM Wuts).

[0454] <Manufacturing Method 21> The intermediates of the compounds of the present invention, the compounds represented by general formulas [II-5] and [II-6], can be manufactured using the compound represented by general formula [II-4] according to the method of the reaction formulas illustrated below.

[0455] [Chemistry 30] (where X) 4 R 1 R 2 and R 10 (This means the same as above).

[0456] That is, the compounds represented by general formula [II-5] and general formula [II-6] can be produced by reacting compound [II-4] with a halogenating agent in a suitable solvent, in the presence or absence of a suitable free radical initiator, in the presence or absence of a suitable base or a suitable acid, and in the presence or absence of light irradiation.

[0457] The amount of halogenating agent that can be used in this reaction can be appropriately selected from the range of 1.0 to 5.0 moles relative to 1 mole of compound [II-4], and preferably 1.0 to 2.5 moles.

[0458] Examples of halogenating agents that can be used in this reaction include chlorine, sulfonyl chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, iodine, N-iodosuccinimide, 1,3-diiodo-5,5-dimethylhydantoin, potassium iodate, or mixtures thereof. Furthermore, the amount of halogenating agent used is appropriately selected from the range of 1.0 to 10 moles relative to 1 mole of compound [II-4], preferably 1.0 to 3.0 moles.

[0459] Examples of free radical initiators that can be used in this reaction include azobisisobutyronitrile (AIBN), azobis(cyclohexanecarboxylonitrile) (ABCN), di-tert-butyl hydroperoxide or tert-butyl hydroperoxide, and benzoyl hydroperoxide. Furthermore, the amount of free radical initiator used is appropriately selected from the range of 0.001 to 0.2 moles relative to 1 mole of compound [II-4], and preferably 0.002 to 0.1 moles.

[0460] 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 mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [II-4] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0461] In this reaction, the reaction can also be carried out under light irradiation.

[0462] The reaction temperature can be selected from any temperature range from 0°C to the reflux temperature in the reaction system, and preferably it can be carried out in the range of 0°C to 100°C.

[0463] The reaction time varies depending on the reaction temperature, the substrate, and the amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0464] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration. This allows for the separation of compounds [II-5] and [II-6]. The separated compounds [II-5] and [II-6] can also be further purified as needed by column chromatography, recrystallization, etc.

[0465] <Manufacturing Method 22> The intermediates of the compounds of the present invention, the compounds represented by general formula [II-8], can be manufactured using the compounds represented by general formula [II-6] according to the method of the reaction formulas illustrated below.

[0466] [Chemistry 31] (In the formula, v represents an integer from 1 to 3, X) 4 R 1 R 2 and R 10 (This means the same as above).

[0467] That is, the compound represented by general formula [II-8] can be manufactured by the following steps: (step 22-1) reacting compound [II-6] with compound [V-15] in a suitable solvent to form compound [II-7], and (step 22-2) reacting compound [II-7] with compound [V-16] in a suitable solvent, in the presence or absence of a suitable acid catalyst.

[0468] (Process 22-1) Examples of compounds [V-15] that can be used in this reaction include silver nitrate or zinc(II) chloride. Furthermore, the amount of compound [V-15] used is appropriately selected from 1.0 to 50 moles relative to 1 mole of compound [II-6], and preferably 1.0 to 10 moles.

[0469] 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; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; nitriles such as acetonitrile and propionitrile; ketones such as acetone and methyl ethyl ketone; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [II-6] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0470] The reaction temperature can usually be selected from any temperature range from -10℃ to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0℃ to 150℃.

[0471] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0472] After the reaction is complete, the reaction mixture is filtered, neutralized by adding water, and then filtered to remove the precipitated solid. Alternatively, it can be extracted with an organic solvent and then concentrated to separate compound [II-7]. The separated compound [II-7] can also be further purified as needed by column chromatography, recrystallization, etc.

[0473] (Process 22-2) Examples of compounds [V-16] that can be used in this reaction include ethylene glycol, 1,3-propanediol, and 1,4-butanediol. Furthermore, the amount of compound [V-16] used is appropriately selected from the range of 1.0 to 50 moles relative to 1 mole of compound [II-7], and preferably 1.0 to 10 moles.

[0474] 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 monoethylene glycol dimethyl ether; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and chlorobenzene; halogenated hydrocarbons such as dichloromethane, chloroform, and 1,2-dichloroethane; alcohols such as 2-propanol, tert-butanol, and methyl cellosolve; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [II-7] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0475] Acid catalysts that can be used in this reaction include, for example, sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid; and carboxylic acids such as formic acid, acetic acid, propionic acid, and trifluoroacetic acid. Furthermore, the amount of acid catalyst used is appropriately selected from the range of 0.01 to 10 moles relative to 1 mole of compound [II-7], preferably 0.01 to 2 moles.

[0476] The reaction temperature can be selected from any temperature range from 0°C to the reflux temperature of the reaction system, and preferably from 20°C to the reflux temperature of the reaction system.

[0477] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0478] After the reaction is complete, the reaction mixture is injected into water, extracted with an organic solvent, and then concentrated to separate compound [II-8]. The separated compound [II-8] can also be further purified as needed by column chromatography, recrystallization, etc.

[0479] <Manufacturing Method 23> The intermediates of the compounds of the present invention, the compounds represented by general formula [II-9], can be manufactured using the compounds represented by general formula [II-5] according to the method of the reaction formulas illustrated below.

[0480] [Chemistry 32] (where X) 4 R 1 R 2 and R 10 (This means the same as above).

[0481] That is, the compound represented by general formula [II-9] can be produced by reacting compound [II-5] with compound [V-17] in a suitable solvent in the presence or absence of a suitable base.

[0482] The amount of compound [V-17] used in this reaction may be appropriately selected from the range of 1.0 to 50 moles relative to 1 mole of compound [II-5], preferably 1.0 to 5.0 moles.

[0483] The acids, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as those in manufacturing method 14.

[0484] After the reaction is complete, the reaction mixture is injected into water, extracted with an organic solvent, and then concentrated to separate compound [II-9]. The separated compound [II-9] can also be further purified as needed by column chromatography, recrystallization, etc.

[0485] <Manufacturing Method 24> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-49], can be manufactured using the compounds represented by general formula [III-44] according to the method of the reaction formulas illustrated below.

[0486] [Chemistry 33] (where R is in the formula) 23 R 24 Each independently represents a hydrogen atom, a C1-C6 alkyl group, and R. 23 R 24 They can form 3-6 membered carbon rings together, R 25 This represents a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group can be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, amino, C1-C6 alkylamino (the amino group can be selected from the substituent group) c Substituents in (C1~C6 alkoxycarbonyl), X 2 Z 2 R 7 R 9 R 15 And Y represents the same meaning as above).

[0487] That is, the compound represented by general formula [III-49] can be manufactured as follows: (Step 24-1) Compound [III-44] is reacted with compound [V-18] in the presence of a suitable base and in a suitable solvent to form compound [III-45], and (Step 24-2) compound [III-45] is hydrolyzed in the presence of a suitable acid or base and in a suitable solvent to form compound [III-46]. Then, (Step 24-3) compound [III-46] is formed into compound [III-47], an active derivative such as an acyl halide or mixed anhydride, in a suitable solvent, in the presence or absence of a suitable catalyst, and (Step 24-4) compound [III-47] is reacted with hydrazine in a suitable solvent, in the presence or absence of a suitable base, in the presence or absence of a suitable catalyst, to form compound [III-48]. Then, (step 24-6) compound [III-48] is reacted with compound [V-19] in a suitable solvent, in the presence or absence of a suitable catalyst, to produce the compound. Alternatively, the compound represented by general formula [III-49] can be produced by the following step: (step 24-5) compound [III-46] is reacted with hydrazine in the presence or absence of a suitable condensing agent and suitable additives, in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base, and in a suitable solvent to form compound [III-48], followed by the above-described (step 24-6).

[0488] (Process 24-1) Examples of compounds [V-18] used in this reaction include iodomethane, dimethyl sulfate, bromoethane, iodoethane, diethyl sulfate, 1-bromopropane, 1-iodopropane, 2-bromopropane, 2-iodoethane, 1,2-dibromoethane, 1,2-diiodoethane, 1,3-dibromopropane, 1,3-diiodopropane, 1,4-dibromobutane, 1,5-dibromopentane, and ethylene carbonate. Furthermore, the amount of compound [V-18] used is appropriately selected from 1.0 to equimolar of the solvent amount relative to 1 mole of compound [III-44], preferably 1.0 to 20 moles.

[0489] 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 bicarbonate and potassium bicarbonate; 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-dimethylpyridine, 4-N,N-dimethylaminopyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. Furthermore, the amount of base used should be appropriately selected from 0.5 to 20 moles relative to 1 mole of compound [III-44], preferably 1.0 to 10 moles.

[0490] Examples of catalysts that can be used in this reaction include alkali metal iodides such as sodium iodide and potassium iodide. Furthermore, the amount of catalyst used is appropriately selected from the range of 0.01 to 0.5 moles relative to 1 mole of compound [III-44], and preferably 0.01 to 0.1 moles.

[0491] 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 monoethylene glycol dimethyl ether; 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-imidazolinone; nitriles such as acetonitrile and propionitrile; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and heptane; pyridines such as pyridine, methylpyridine, and dimethylpyridine; tertiary amines such as triethylamine and tributylamine; water or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-44] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0492] The reaction temperature can usually be selected from any temperature range from -78°C to the reflux temperature in the reaction system, and preferably can be carried out in the range of 0°C to 100°C.

[0493] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 10 minutes to 72 hours.

[0494] After the reaction is complete, the reaction mixture is injected into water, extracted with an organic solvent, and then concentrated to separate compound [III-45]. The separated compound [III-45] can also be further purified as needed by column chromatography, recrystallization, etc.

[0495] (Process 24-2) The acids, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as in (Step 1-1).

[0496] After the reaction is complete, the reaction mixture is neutralized by adding water, and the precipitated solid is then filtered out or extracted with an organic solvent and concentrated. This process can separate compound [III-46]. The separated compound [III-46] can also be further purified as needed by column chromatography, recrystallization, etc.

[0497] (Process 24-3) The reagents, acids, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction to convert compound [III-46] into compound [III-47] are the same as in (steps 1-2).

[0498] (Process 24-4) Examples of hydrazine used in this reaction include anhydrous hydrazine, hydrazine monohydrate, hydrazine hydrochloride, hydrazine dihydrochloride, and hydrazine sulfate. Furthermore, the amount of hydrazine used is typically selected from the range of 0.5 to 5.0 moles relative to 1 mole of compound [III-47], and preferably from 0.5 to 2.5 moles.

[0499] The base, solvent, reaction temperature, and reaction time that can be used in this reaction are the same as those in (steps 1-3).

[0500] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-48]. The separated compound [III-48] can also be further purified as needed by column chromatography, recrystallization, etc.

[0501] (Process 24-5) Examples of hydrazine used in this reaction include anhydrous hydrazine, hydrazine monohydrate, hydrazine hydrochloride, hydrazine dihydrochloride, and hydrazine sulfate. Furthermore, the amount of hydrazine used is typically selected from the range of 0.5 to 5.0 moles relative to 1 mole of compound [III-46], and preferably from 0.5 to 2.5 moles.

[0502] The condensing agents, catalysts, additives, bases, solvents, reaction temperatures, and reaction times that can be used in this reaction are the same as in (steps 1-4).

[0503] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is filtered out or extracted with an organic solvent and then concentrated, thereby separating compound [III-48]. The separated compound [III-48] can also be further purified as needed by column chromatography, recrystallization, etc.

[0504] (Process 24-6) Examples of compounds [V-19] used in this reaction include orthoesters such as trimethyl orthoformate, triethyl orthoformate, and trimethyl orthoacetate; acyl chlorides such as acetyl chloride, propionyl chloride, methyl chloroglyoxylate, and ethyl chloroglyoxylate; carboxylic anhydrides such as acetic anhydride and propionic anhydride; and cyanogen bromide, methyl isothiocyanate, and dimethylcarbamoyl chloride. Furthermore, the amount of compound [V-19] used is appropriately selected from 1.0 to equimolar of the solvent volume relative to 1 mole of compound [III-48], preferably 1.0 to 50 moles.

[0505] When a base is used in this reaction, examples of usable bases 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-dimethylpyridine; alkali metal carbonates such as sodium carbonate and potassium carbonate; and inorganic bases such as alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate. Furthermore, the amount of base used should be appropriately selected from 0.1 to 10 moles relative to 1 mole of compound [III-48], preferably 0.1 to 5.0 moles.

[0506] Examples of acids that can be used in this reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, and sulfuric acid; carboxylic acids such as acetic acid and trifluoroacetic acid; and sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid. Furthermore, the amount of acid used should be appropriately selected from the range of 1.0 to 1000 moles relative to 1 mole of compound [III-48], preferably 1.0 to 100 moles.

[0507] 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; 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-imidazolinone; ethers such as diethyl ether, cyclopentyl methyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, and 1,4-dioxane; or mixtures thereof. Furthermore, the amount of solvent used relative to 1 mole of compound [III-48] is 0.1 to 1000 liters, preferably 0.2 to 100 liters.

[0508] The reaction temperature can be selected from any temperature range from -20℃ to the reflux temperature in the reaction system, and preferably it can be carried out in the range of 0℃ to 120℃.

[0509] The reaction time varies depending on the reaction temperature, substrate, and amount of reaction, and typically ranges from 1 minute to 72 hours.

[0510] After the reaction is complete, the reaction mixture is injected into water, and the precipitated solid is removed by filtration or by extraction with an organic solvent followed by concentration, thereby separating compound [III-49]. The separated compound [III-49] can also be further purified as needed by column chromatography, recrystallization, etc.

[0511] <Manufacturing Method 25> The intermediates of the compounds of the present invention, the compounds represented by general formula [III-49], can be manufactured by using the compounds represented by general formula [III-46] or general formula [III-47] according to the method of the reaction formulas illustrated below.

[0512] [Chemistry 34] (where X) 2 Z 2 R 7 R 9 , R23 R 24 R 25 And Y represents the same meaning as above).

[0513] That is, the compound represented by general formula [III-49] can be manufactured by the following steps: (Step 25-1) reacting compound [III-46] with compound [V-20] in the presence or absence of a suitable condensing agent and suitable additives, in the presence or absence of a suitable catalyst, in the presence or absence of a suitable base, and in a suitable solvent to form compound [III-50], and then (Step 25-4) reacting compound [III-50] with compound [V-22] in a suitable solvent, in the presence...

Claims

1. An agricultural and horticultural plant disease control agent, characterized in that, It contains nicotinamide derivatives or salts thereof represented by general formula [I] as active ingredients. In the formula, Q indicates -NR a R b Or nitro, W represents an oxygen atom or a sulfur atom. Y represents an oxygen atom or a sulfur atom (the sulfur atom may or may not be oxidized by one or two oxygen atoms). A 1 This indicates an oxygen atom, a sulfur atom (which may or may not be oxidized by one or two oxygen atoms), -CH2-, or -NR. c -, A 2 Represents -CH- or nitrogen atom, R 1 This represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyl, or C1-C6 alkoxy R 2 and R 3 Each of the following independently represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (which may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 alkoxy C1~C6 alkyl, C1~C6 alkylthio C1~C6 alkyl, C1~C6 alkylsulfinyl C1~C6 alkyl, C1~C6 alkylsulfonyl C1~C6 alkyl, C1~C6 alkylamino C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, cyano, formyl, carboxyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, amino carbonyl, C1-C6 alkylamino carbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C3~C8 cycloalkylaminocarbonyl (the cycloalkyl group may or may not be selected from the substituent group) β The amino group is substituted with a substituent, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C6~C) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (substitution of one or more substituents); Furthermore, R 2 With R 3 They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which may or may not be oxidized by one or two oxygen atoms), and NR. u The 0 to 1 atoms or groups of atoms in the ring together form a 5 to 6-membered ring, which is substituted, or not substituted, by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 alkoxy, or oxo groups. R 4 This indicates a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β The substituents in the group are C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, formyl, C1-C6 alkyl carbonyl, or C1-C6 alkoxy carbonyl. L represents L-1, L-2, or L-3. R 5 This indicates a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarbonyl, C6-C6 alkylyl, C6-C6 alkylyl, C2-C6 alkylyl ... 12 aryl (which may or may not be selected from the substituent group) α (one or more substituents), cyano C1~C6 alkyl, or C6~C 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (with one or more substituents in the group) R 6 This represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyl, or C1-C6 alkoxy R 7 This represents hydrogen atoms, halogen atoms, hydroxyl groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (with one or more substituents in the group) R 8 Represents hydrogen atom, halogen atom, hydroxyl group, mercapto group, cyano group, nitro group, -CR d R e R f -OR h -NR i R k methyl, C3-C8 cycloalkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3-C8 cycloalkenyl, C2-C6 alkenyl, C2-C6 ynynyl, tris(C1-C6 alkyl)silylC2-C6 ynynyl, C3-C8 cycloalkylC2-C6 ynynyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkylthio, C1~C6 alkylsulfinyl, C1~C6 alkylsulfonyl, C3~C8 cycloalkylthio (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 haloalkylthio, C1~C6 haloalkylsulfinyl, C1~C6 haloalkylsulfonyl, C1~C6 alkoxyC1~C6 alkylthio, C1~C6 alkoxyC1~C6 alkylsulfinyl, C1~C6 alkoxyC1~C6 alkylsulfonyl, cyanothio, C1~C6 alkylcarbonylthio, aminosulfonyl, C1~C6 alkylaminosulfonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 arylthio (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfinyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylthio groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroarylsulfinyl group (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylsulfonyl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), 3- to 6-membered heterocyclic thio groups (the heterocyclic group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic sulfinyl group (the heterocyclic group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic sulfonyl group (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), formyl group, carboxyl group, C1-C6 alkyl carbonyl group, C3-C8 cycloalkyl carbonyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkoxy-C1~C6 alkyl carbonyl, C1~C6 alkoxy carbonyl, amino carbonyl, C1~C6 alkylamino carbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C3~C8 cycloalkylaminocarbonyl (the cycloalkyl group may or may not be selected from the substituent group) β The amino group is substituted with a substituent, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group), 3-6 membered heterocyclic carbonyl groups (the heterocyclic group may or may not be selected from the substituent group). α (one or more substituents in the middle), C6~C 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group may or may not be selected from the substituent group) α (substitution of one or more substituents), -C (=NR) m )R n base, or -C(R) o )=CR p (R s )base, R 9 This represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which may or may not be selected from the substituent group) α (one or more substituents), or 5-12 heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group). α (with one or more substituents in the group) R x and R y Each independently represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group; further, R x and R y They can form oxygen groups together. R z Indicates hydrogen atom, halogen atom, or C1~C6 alkyl group. R a and R b Each of these elements independently represents a hydrogen atom, hydroxyl group, amino group, C1-C6 alkyl group, or C3-C8 cycloalkyl group (which may or may not be selected from the substituent group). β Substituents in (C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl, C6-C6) 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), formyl group, C1-C6 alkyl carbonyl group, C1-C6 haloalkyl carbonyl group, C1-C6 alkoxy C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, amino carbonyl group, C1-C6 alkylamino carbonyl group (the amino group may or may not be selected from the substituent group) γ Substituents in the group), 3-6 membered heterocyclic groups (the heterocyclic group may or may not be selected from the substituent group). α (more than one substituent in it), in addition, R a and R b They can together form (=CH)-C1~C6 alkyl groups, (=CH)-C6~C 12 aryl (which may or may not be selected from the substituent group) α (substituents of one or more groups) or (=CH)-N(C1~C6 alkyl)2, further, R a With R b They can bond with each other to atoms selected from carbon, oxygen, sulfur (which may or may not be oxidized by one or two oxygen atoms), and NR. u The 0 to 1 atoms or groups of atoms together form a nitrogen-containing 4 to 6-membered ring, which is substituted, or not substituted, by one or more chemically acceptable substituents selected from halogen atoms, C1 to C6 alkyl groups, C1 to C6 haloalkyl groups, C1 to C6 alkoxy groups, or oxo groups. R c Indicates a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 alkyl carbonyl group. R d R e Each of the following groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (which may or may not be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy or tris(C1-C6 alkyl)silyloxy, in addition, R d and R e They can form =CH2 together; furthermore, R d With R e They can bond with each other to atoms selected from carbon, oxygen, sulfur (which may or may not be oxidized by one or two oxygen atoms), and NR. u The 0 to 2 atoms or groups together form a 3 to 6-membered ring, which is substituted, or not substituted, by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 haloalkyl, C1 to C6 alkoxy, or oxo groups. R f This indicates a halogen atom, hydroxyl group, mercapto group, amino group, cyano group, nitro group, C1-C6 alkyl group, or C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 ynyl, C3~C8 cycloalkyl, C2~C6 ynyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C8 cycloalkyloxy C1-C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C6-C6 alkyl) 12 aryloxy C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic oxy-C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents in the group), 5-12 membered heteroaryloxy C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), mercapto C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C3-C8 cycloalkylthio C1-C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 haloalkylthio-C1~C6 alkyl, C1~C6 haloalkylsulfinyl-C1~C6 alkyl, C1~C6 haloalkylsulfonyl-C1~C6 alkyl, C1~C6 alkylaminosulfonyl-C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (e.g., cyanothio C1-C6 alkyl, amino C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C3-C8 cycloalkylamino C1-C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β The amino group is substituted with a substituent, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C1-C6 alkyl halogenated amino C1-C6 alkyl group, where the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1-C6 alkyl carbonyl amino C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkoxycarbonyl amino C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkylsulfonylamino C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1-C6 haloalkylsulfonylamino C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in the group), aminosulfonylamino C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkylaminosulfonylaminoC1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (e.g., cyano C1-C6 alkyl, formyl C1-C6 alkyl, carboxyl C1-C6 alkyl, C1-C6 alkyl carbonyl C1-C6 alkyl, C1-C6 alkoxy carbonyl C1-C6 alkyl, amino carbonyl C1-C6 alkyl, C1-C6 alkyl amino carbonyl C1-C6 alkyl (where the amino group is or is not selected from the substituent group) γ Substituents in (C6~C) 12 arylaminocarbonyl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group), hydroxyaminocarbonyl C1-C6 alkyl, C1-C6 alkoxyaminocarbonyl C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl carbonyl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylcarbonyl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (One or more substituents are substituted), 3-6 membered heterocyclic carbonyl C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), aminothiocarbonyl C1-C6 alkyl, C1-C6 alkylaminothiocarbonyl C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C1~C6 alkyl)-C (=NR) m )R n C6~C 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, C3-C8 cycloalkyloxy (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in the group), C1-C6 haloalkyloxy groups, C3-C8 cycloalkyl C1-C6 alkoxy groups (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in C1-C6 alkoxy groups, C1-C6 alkoxy groups, C6-C6 alkoxy groups) 12 Aryl C1~C6 alkoxy (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkoxy groups (the heteroaryl group may or may not be selected from the substituent group) α (One or more substituents are substituted), 3-6 membered heterocyclic C1-C6 alkoxy groups (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkyl carbonyloxy group, C3-C8 cycloalkyl carbonyloxy group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), aminocarbonyloxy group, C6~C 12 aryloxy group (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 heteroaryloxy groups (the heteroaryl group may or may not be selected from the substituent group) α (One or more substituents are substituted), 3-6 membered heterocyclic oxygen groups (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylthio (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkyl C1-C6 alkylthio (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl C1~C6 alkylsulfinyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl C1~C6 alkylsulfonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkoxy-C1~C6 alkylthio, C1~C6 alkoxy-C1~C6 alkylsulfinyl, C1~C6 alkoxy-C1~C6 alkylsulfonyl, cyanothio, C1~C6 alkylcarbonylthio, aminosulfonyl, C1~C6 alkylaminosulfonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 arylthio (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfinyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylthio groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroarylsulfinyl group (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylsulfonyl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents in the group), C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C3-C8 cycloalkylamino (the cycloalkyl group may or may not be selected from the substituent group) β The amino group is substituted with a substituent, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C1-C6 alkyl halogenated amino groups, where the amino group may or may not be selected from the substituent group) γ Substituents in (substituents), aminocarbonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkylamino carbonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkoxycarbonyl amino (the amino group may or may not be selected from the substituent group) α (substituents in the group), C1~C6 alkylsulfonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 haloalkylsulfonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), aminosulfonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkylaminosulfonylamino (the amino group may or may not be selected from the substituent group) γ Substituents in the group), 5-12 membered heteroarylamino groups (the heteroaryl group may or may not be selected from the substituent group). α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group include: formyl group, carboxyl group, C1-C6 alkyl carbonyl group, and C3-C8 cycloalkyl carbonyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 alkoxy-C1-C6 alkyl-carbonyl, C1-C6 alkoxy-carbonyl, C6-C6) 12 aryloxycarbonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryloxycarbonyl (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), amino carbonyl, C1-C6 alkylamino carbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), hydroxyaminocarbonyl, C1~C6 alkoxyaminocarbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group), 5-12 membered heteroarylaminocarbonyl (the heteroaryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group), 3-6 membered heterocyclic amino carbonyl groups (the heterocyclic group may or may not be selected from the substituent group). α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (e.g., aminothiocarbonyl, C1-C6 alkylaminothiocarbonyl, where the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl carbonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylcarbonyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic carbonyl groups (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group may or may not be selected from the substituent group) α (substitution of one or more substituents), or -C (=NR) m )R n base, R h This indicates a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 alkynyl, hydroxy C1~C6 alkyl, C1~C6 alkoxy C1~C6 alkyl, C3~C8 cycloalkyloxy C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C6-C6 alkyl) 12 aryloxy C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the group), 5-12 membered heteroaryloxy C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic oxy-C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), mercapto C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C3-C8 cycloalkylthio C1-C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 haloalkylthio-C1-C6 alkyl, C1-C6 haloalkylsulfinyl-C1-C6 alkyl, C1-C6 haloalkylsulfonyl-C1-C6 alkyl, C6-C 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylaminosulfonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), formyl group, C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, amino carbonyl group, C1-C6 alkylamino carbonyl group (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C6~C) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group may or may not be selected from the substituent group) α (substituents of one or more groups), -N=CH-(C1~C6 alkyl), or -N=C(C1~C6 alkyl)2, R i This indicates a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (e.g., cyano C1-C6 alkyl, C6-C6 alkyl) 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which may or may not be selected from the substituent group) α (one or more substituents), or 5-12 heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group). α (with one or more substituents in the group) R k This indicates a hydrogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 alkynyl, hydroxy C1~C6 alkyl, C1~C6 alkoxy C1~C6 alkyl, C3~C8 cycloalkyloxy C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C1-C6 alkylthiolated C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, cyano C1-C6 alkyl, C6-C 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl (the amino group may or may not be selected from the substituent group) γ Substituents in the group (e.g., C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl, where the cycloalkyl group is or is not selected from the substituent group) β Substituents in (C1-C6 haloalkyl carbonyl, C1-C6 alkoxy C1-C6 alkyl carbonyl, cyano C1-C6 alkyl carbonyl, C6-C6 alkyl carbonyl) 12 Aryl C1~C6 alkyl carbonyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl carbonyl (the heteroaryl group may or may not be selected from the substituent group) α (One or more substituents are substituted), 3-6 membered heterocyclic C1-C6 alkyl carbonyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl carbonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylcarbonyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic carbonyl groups (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (with one or more substituents in the group) Furthermore, R i With R k They can bond with each other to atoms selected from carbon, oxygen, sulfur (which may or may not be oxidized by one or two oxygen atoms), and NR. u One or more atoms or groups of atoms together form a nitrogen-containing 4-6 membered ring, wherein the nitrogen-containing 4-6 membered ring is or is not selected from halogen atoms, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, amino carbonyl, C1-C6 alkyl amino carbonyl (where the amino group is or is not selected from the substituent group) γ Substituents in (C1-C6 alkyl carbonyl amino groups) (the amino group may or may not be selected from the substituent group) γ (substituent substitution in the group), or chemically acceptable substitution of one or more substituents in the oxo group. R m This indicates hydroxyl, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C8 cycloalkyloxy (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyloxy groups, C1-C6 alkylamino groups (the amino group may or may not be selected from the substituent group) γ (substituents in the group), or C1-C6 alkylcarbonylamino (the amino group may or may not be selected from the substituent group). γ (substituents in the text) R n This represents a hydrogen atom, a halogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (with one or more substituents in the group) R o This indicates cyano, C1-C6 alkyl, or C3-C8 cycloalkyl (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylcarbonyl, C3-C8 cycloalkylcarbonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkoxycarbonyl or C1~C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (with one or more substituents in the group) R p This indicates a hydrogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 alkoxycarbonyl, or C1-C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the text) R s This indicates cyano, C1-C6 alkyl, or C3-C8 cycloalkyl (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 alkoxycarbonyl, or C1-C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the text) Furthermore, R p With R s They can bond with each other to form a 5-6 membered ring with 0-2 atoms or groups selected from carbon atoms, oxygen atoms, and sulfur atoms (which may or may not be oxidized by one or two oxygen atoms), and the 5-6 membered ring may or may not be substituted by one or more chemically acceptable substituents selected from C1-C6 alkyl, C1-C6 alkoxy, or oxo groups. R u Indicates a hydrogen atom or a C1-C6 alkyl group. Substitute basis set α This indicates a halogen atom, hydroxyl group, mercapto group, amino group, cyano group, nitro group, C1-C6 alkyl group, C1-C6 haloalkyl group, or C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in the group), C3-C8 halocycloalkyl groups (the halocycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkoxy, C1~C6 alkyl, C2~C6 alkenyl, C2~C6 ynyl, C3~C8 cycloalkyl, C2~C6 ynyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 alkoxy groups, C3-C8 cycloalkyloxy groups (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 alkyl oxy, C1-C6 alkoxy, C6-C6 alkoxy) 12 aryl C1-C6 alkoxy (the aryl group may or may not be substituted by one or more substituents selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, cyano), C2-C6 alkenoxy, C2-C6 alkynoxy, tris(C1-C6 alkyl)silyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ Substituents in (C1-C6 alkyl carbonyl amino groups) (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl (the aryl group may or may not be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ Substituents in the group, substitution of one or more substituents in the cyano group, 5-12 membered heteroaryl groups (which are substituted or not substituted by one or more substituents selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino, di(C1-C6 alkyl)amino, cyano), oxo groups, or -C (=NR) m )R n base, Substitute basis set β This indicates a halogen atom, hydroxyl group, amino group, cyano group, C1-C6 alkyl group, C3-C8 cycloalkyl group (which may or may not be substituted by a substituent selected from C1-C6 alkyl or C1-C6 haloalkyl group), C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 alkyl group, C1-C6 alkoxy group, C1-C6 alkyl carbonyl amino group (which may or may not be selected from the substituent group) γ (substituents in the group), C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, amino carbonyl, C1-C6 alkylamino carbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl (the aryl group may or may not be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ The following groups may be substituted: (substituents in the group), (substituents in the cyano group), (substituents in the ... γ (substituent substitution in the group), (substituent substitution of one or more substituents in the cyano group), Substitute basis set γ It represents C1~C6 alkyl, C1~C6 haloalkyl, C3~C8 cycloalkyl (which is substituted or not substituted by a substituent selected from C1~C6 alkyl or C1~C6 haloalkyl), C1~C6 alkoxy C1~C6 alkyl, C1~C6 haloalkyloxy C1~C6 alkyl, cyano C1~C6 alkyl carbonyl, C1~C6 haloalkyl carbonyl, or C1~C6 alkoxy carbonyl.

2. Nicotinamide derivatives or salts thereof represented by general formula [I] In the formula, Q indicates -NR a R b Or nitro, W represents an oxygen atom or a sulfur atom. Y represents an oxygen atom or a sulfur atom (the sulfur atom may or may not be oxidized by one or two oxygen atoms). A 1 This indicates an oxygen atom, a sulfur atom (which may or may not be oxidized by one or two oxygen atoms), -CH2-, or -NR. c , A 2 Represents -CH- or nitrogen atom, R 1 This represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl or C1~C6 alkoxy groups, R 2 and R 3 Each of the following independently represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (which may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 alkoxy C1~C6 alkyl, C1~C6 alkylthio C1~C6 alkyl, C1~C6 alkylsulfinyl C1~C6 alkyl, C1~C6 alkylsulfonyl C1~C6 alkyl, C1~C6 alkylamino C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, cyano, formyl, carboxyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, amino carbonyl, C1-C6 alkylamino carbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C3~C8 cycloalkylaminocarbonyl (the cycloalkyl group may or may not be selected from the substituent group) β The amino group is substituted with a substituent, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C6~C) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (more than one substituent in R), further, R 2 With R 3 They can bond with each other to atoms selected from carbon, oxygen, sulfur (which may or may not be oxidized by one or two oxygen atoms), and NR. u The 0 to 1 atoms or groups of atoms in the ring together form a 5 to 6-membered ring, which is substituted, or not substituted, by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 alkoxy, or oxo groups. R 4 This indicates a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β The substituents in the group are C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, formyl, C1-C6 alkyl carbonyl, or C1-C6 alkoxy carbonyl. L represents L-1, L-2, or L-3. R 5 This indicates a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkoxy, C1-C6 alkyl, C1-C6 alkylcarbonyl, C6-C6 alkylyl, C6-C6 alkylyl, C2-C6 alkylyl ... 12 aryl (which may or may not be selected from the substituent group) α (one or more substituents), cyano C1~C6 alkyl, or C6~C 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (with one or more substituents in the group) R 6 This represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, methoxy, or C3~C6 alkoxy, R 7 This represents hydrogen atoms, halogen atoms, hydroxyl groups, C1-C6 alkyl groups, and C3-C8 cycloalkyl groups (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (with one or more substituents in the group) R 8 Indicates hydroxyl, mercapto, cyano, -CR d R e R f -OR h -NR i R k C3-C8 cycloalkyl groups (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3-C8 cycloalkenyl, C2-C6 alkenyl, C2-C6 ynynyl, tris(C1-C6 alkyl)silylC2-C6 ynynyl, C3-C8 cycloalkylC2-C6 ynynyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkylthio, C1~C6 alkylsulfinyl, C1~C6 alkylsulfonyl, C3~C8 cycloalkylthio (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 haloalkylthio, C1~C6 haloalkylsulfinyl, C1~C6 haloalkylsulfonyl, C1~C6 alkoxyC1~C6 alkylthio, C1~C6 alkoxyC1~C6 alkylsulfinyl, C1~C6 alkoxyC1~C6 alkylsulfonyl, cyanothio, C1~C6 alkylcarbonylthio, aminosulfonyl, C1~C6 alkylaminosulfonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 arylthio (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfinyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylthio groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroarylsulfinyl group (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylsulfonyl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), 3- to 6-membered heterocyclic thio groups (the heterocyclic group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic sulfinyl group (the heterocyclic group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic sulfonyl group (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), formyl group, carboxyl group, C1-C6 alkyl carbonyl group, C3-C8 cycloalkyl carbonyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkoxy-C1~C6 alkyl carbonyl, C1~C6 alkoxy carbonyl, amino carbonyl, C2~C6 alkylamino carbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C3~C8 cycloalkylaminocarbonyl (the cycloalkyl group may or may not be selected from the substituent group) β The amino group is substituted with a substituent, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C6~C) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group may or may not be selected from the substituent group) α (substitution of one or more substituents), -C (=NR) m )R n base, or -C(R) o )=CR p (R s )base, R 9 This represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which may or may not be selected from the substituent group) α (one or more substituents), or 5-12 heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group). α (with one or more substituents in the group) R x and R y Each independently represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group; further, R x and R y They can form oxygen groups together. R z Indicates hydrogen atom, halogen atom, or C1~C6 alkyl group. R a This indicates a hydrogen atom, hydroxyl group, amino group, C1-C6 alkyl group, or C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in the group), hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, 5-12 heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), formyl group, C1-C6 alkyl carbonyl group, C1-C6 haloalkyl carbonyl group, C1-C6 alkoxy C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, amino carbonyl group, C1-C6 alkylamino carbonyl group (the amino group may or may not be selected from the substituent group) γ Substituents in the group), 3-6 membered heterocyclic groups (the heterocyclic group may or may not be selected from the substituent group). α (with one or more substituents in the group) R b Represents a hydrogen atom. In addition, R a and R b They can together form (=CH)-C1~C6 alkyl groups, (=CH)-C6~C 12 aryl (which may or may not be selected from the substituent group) α (substituents of one or more groups) or =CH-N(C1~C6 alkyl)2, R c Represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 alkyl carbonyl group. R d R e Each of the following groups independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a mercapto group, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (which may or may not be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkoxy or tris(C1-C6 alkyl)silyloxy; in addition, R d and R e They can form =CH2 together, and further, R d With R e They can bond with each other to atoms selected from carbon, oxygen, sulfur (which may or may not be oxidized by one or two oxygen atoms), and NR. u The 0 to 2 atoms or groups together form a 3 to 6-membered ring, which is substituted, or not substituted, by one or more chemically acceptable substituents selected from C1 to C6 alkyl, C1 to C6 haloalkyl, C1 to C6 alkoxy, or oxo groups. R f This indicates a chlorine atom, bromine atom, iodine atom, hydroxyl group, mercapto group, amino group, cyano group, nitro group, C1-C6 alkyl group, or C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 ynyl, C3~C8 cycloalkyl, C2~C6 ynyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C3-C8 cycloalkyloxy C1-C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C6-C6 alkyl) 12 aryloxy C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic oxy-C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents in the group), 5-12 membered heteroaryloxy C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), mercapto C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C3-C8 cycloalkylthio C1-C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 haloalkylthio-C1~C6 alkyl, C1~C6 haloalkylsulfinyl-C1~C6 alkyl, C1~C6 haloalkylsulfonyl-C1~C6 alkyl, C1~C6 alkylaminosulfonyl-C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (e.g., cyanothio C1-C6 alkyl, amino C1-C6 alkyl, C1-C6 alkylamino C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C3-C8 cycloalkylamino C1-C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β The amino group is substituted with a substituent, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C1-C6 alkyl halogenated amino C1-C6 alkyl group, where the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1-C6 alkyl carbonyl amino C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkoxycarbonyl amino C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkylsulfonylamino C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1-C6 haloalkylsulfonylamino C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in the group), aminosulfonylamino C1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkylaminosulfonylaminoC1~C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (e.g., cyano C1-C6 alkyl, formyl C1-C6 alkyl, carboxyl C1-C6 alkyl, C1-C6 alkyl carbonyl C1-C6 alkyl, C1-C6 alkoxy carbonyl C1-C6 alkyl, amino carbonyl C1-C6 alkyl, C1-C6 alkyl amino carbonyl C1-C6 alkyl (where the amino group is or is not selected from the substituent group) γ Substituents in (C6~C) 12 arylaminocarbonyl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group), hydroxyaminocarbonyl C1-C6 alkyl, C1-C6 alkoxyaminocarbonyl C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl carbonyl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents), 5-12 membered heteroarylcarbonyl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (One or more substituents are substituted), 3-6 membered heterocyclic carbonyl C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), aminothiocarbonyl C1-C6 alkyl, C1-C6 alkylaminothiocarbonyl C1-C6 alkyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C1~C6 alkyl)-C (=NR) m )R n C6~C 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkoxy, C3-C8 cycloalkyloxy (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in the group), C1-C6 haloalkyloxy groups, C3-C8 cycloalkyl C1-C6 alkoxy groups (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in C1-C6 alkoxy groups, C1-C6 alkoxy groups, C6-C6 alkoxy groups) 12 Aryl C1~C6 alkoxy (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkoxy groups (the heteroaryl group may or may not be selected from the substituent group) α (One or more substituents are substituted), 3-6 membered heterocyclic C1-C6 alkoxy groups (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkyl carbonyloxy group, C3-C8 cycloalkyl carbonyloxy group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), aminocarbonyloxy group, C6~C 12 aryloxy group (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 heteroaryloxy groups (the heteroaryl group may or may not be selected from the substituent group) α (One or more substituents are substituted), 3-6 membered heterocyclic oxygen groups (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C3-C8 cycloalkylthio (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C3-C8 cycloalkyl C1-C6 alkylthio (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl C1~C6 alkylsulfinyl group (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl C1~C6 alkylsulfonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkoxy-C1~C6 alkylthio, C1~C6 alkoxy-C1~C6 alkylsulfinyl, C1~C6 alkoxy-C1~C6 alkylsulfonyl, cyanothio, C1~C6 alkylcarbonylthio, aminosulfonyl, C1~C6 alkylaminosulfonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 arylthio (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfinyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 arylsulfonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylthio groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroarylsulfinyl group (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylsulfonyl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents in the group), C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C3-C8 cycloalkylamino (the cycloalkyl group may or may not be selected from the substituent group) β The amino group is substituted with a substituent, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C1-C6 alkyl halogenated amino groups, where the amino group may or may not be selected from the substituent group) γ Substituents in (substituents), aminocarbonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkylamino carbonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkoxycarbonyl amino (the amino group may or may not be selected from the substituent group) α (substituents in the group), C1~C6 alkylsulfonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 haloalkylsulfonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), aminosulfonylamino (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1~C6 alkylaminosulfonylamino (the amino group may or may not be selected from the substituent group) γ Substituents in the group), 5-12 membered heteroarylamino groups (the heteroaryl group may or may not be selected from the substituent group). α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group include: formyl group, carboxyl group, C1-C6 alkyl carbonyl group, and C3-C8 cycloalkyl carbonyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 alkoxy-C1-C6 alkyl-carbonyl, C1-C6 alkoxy-carbonyl, C6-C6) 12 aryloxycarbonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryloxycarbonyl (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), amino carbonyl, C1-C6 alkylamino carbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), hydroxyaminocarbonyl, C1~C6 alkoxyaminocarbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group), 5-12 membered heteroarylaminocarbonyl (the heteroaryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in the group), 3-6 membered heterocyclic amino carbonyl groups (the heterocyclic group may or may not be selected from the substituent group). α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (e.g., aminothiocarbonyl, C1-C6 alkylaminothiocarbonyl, where the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl carbonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylcarbonyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic carbonyl groups (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group may or may not be selected from the substituent group) α (substitution of one or more substituents), or -C (=NR) m )R n base, R h This indicates a hydrogen atom, a C2-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 alkynyl, hydroxy C1~C6 alkyl, C1~C6 alkoxy C1~C6 alkyl, C3~C8 cycloalkyloxy C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C6-C6 alkyl) 12 aryloxy C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents in the group), 5-12 membered heteroaryloxy C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic oxy-C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), mercapto C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, C3-C8 cycloalkylthio C1-C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkyl sulfinyl C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C3~C8 cycloalkylsulfonyl C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 haloalkylthio-C1-C6 alkyl, C1-C6 haloalkylsulfinyl-C1-C6 alkyl, C1-C6 haloalkylsulfonyl-C1-C6 alkyl, C6-C 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylaminosulfonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the group), formyl group, C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, amino carbonyl group, C1-C6 alkylamino carbonyl group (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 arylaminocarbonyl (the aryl group may or may not be selected from the substituent group) α One or more substituents are substituted in the amino group, and the amino group may or may not be selected from the group consisting of substituents. γ Substituents in (C6~C) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3- to 6-membered heterocyclic groups (the heterocyclic group may or may not be selected from the substituent group) α (substituents of one or more groups), -N=CH-(C1~C6 alkyl), or -N=C(C1~C6 alkyl)2, R i This indicates a hydrogen atom, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (e.g., cyano C1-C6 alkyl, C6-C6 alkyl) 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which may or may not be selected from the substituent group) α (one or more substituents), or 5-12 heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group). α (with one or more substituents in the group) R k This indicates a hydrogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1~C6 haloalkyl, C2~C6 alkenyl, C2~C6 alkynyl, hydroxy C1~C6 alkyl, C1~C6 alkoxy C1~C6 alkyl, C3~C8 cycloalkyloxy C1~C6 alkyl (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 alkyl halogenated C1-C6 alkyl, C1-C6 alkylthiolated C1-C6 alkyl, C1-C6 alkylsulfinyl C1-C6 alkyl, C1-C6 alkylsulfonyl C1-C6 alkyl, cyano C1-C6 alkyl, C6-C 12 Aryl C1~C6 alkyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic C1-C6 alkyl (the heterocyclic group may or may not be selected from the substituent group) α (1 or more substituents in the group), 5-12 membered heteroaryl C1-C6 alkyl (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylaminosulfonyl (the amino group may or may not be selected from the substituent group) γ Substituents in the group (e.g., C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl, where the cycloalkyl group is or is not selected from the substituent group) β Substituents in (C1-C6 haloalkyl carbonyl, C1-C6 alkoxy C1-C6 alkyl carbonyl, cyano C1-C6 alkyl carbonyl, C6-C6 alkyl carbonyl) 12 Aryl C1~C6 alkyl carbonyl (the aryl group may or may not be selected from the substituent group) α (one or more substituents), 5-12 membered heteroaryl C1-C6 alkyl carbonyl (the heteroaryl group may or may not be selected from the substituent group) α (One or more substituents are substituted), 3-6 membered heterocyclic C1-C6 alkyl carbonyl (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl carbonyl (the aryl group may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroarylcarbonyl (the heteroaryl group may or may not be selected from the substituent group) α (1 or more substituents), 3-6 membered heterocyclic carbonyl groups (the heterocyclic group may or may not be selected from the substituent group) α (one or more substituents in the middle), C6~C 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (with one or more substituents in the group) Furthermore, R i With R k They can bond with each other and be selected from carbon atoms, oxygen atoms, sulfur atoms (which may or may not be oxidized by one or two oxygen atoms), and NR. u One or more atoms or groups of atoms together form a nitrogen-containing 4-6 membered ring, wherein the nitrogen-containing 4-6 membered ring is or is not selected from halogen atoms, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, amino carbonyl, C1-C6 alkyl amino carbonyl (where the amino group is or is not selected from the substituent group) γ Substituents in (C1-C6 alkyl carbonyl amino groups) (the amino group may or may not be selected from the substituent group) γ (substituent substitution in the group), or chemically acceptable substitution of one or more substituents in the oxo group. R m This indicates hydroxyl, amino, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C3-C8 cycloalkyloxy (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in the group), C1-C6 haloalkyloxy groups, C1-C6 alkylamino groups (the amino group may or may not be selected from the substituent group) γ (substituents in the group), or C1-C6 alkylcarbonylamino (the amino group may or may not be selected from the substituent group). γ (substituents in the text) R n This represents a hydrogen atom, a halogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in (C1-C6 alkyl halogens, C1-C6 alkoxy groups, C6-C6 alkyl halogens) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (with one or more substituents in the group) R o This indicates cyano, C1-C6 alkyl, or C3-C8 cycloalkyl (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylcarbonyl, C3-C8 cycloalkylcarbonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkoxycarbonyl or C1~C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl (which may or may not be selected from the substituent group) α (1 or more substituents), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be selected from the substituent group) α (one or more substituents), or a 3- to 6-membered heterocyclic group (which may or may not be selected from the substituent group). α (with one or more substituents in the group) R p This indicates a hydrogen atom, a cyano group, a C1-C6 alkyl group, or a C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 alkoxycarbonyl, or C1-C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the text) R s This indicates cyano, C1-C6 alkyl, or C3-C8 cycloalkyl (the cycloalkyl group may or may not be selected from the substituent group). β (substituents in the group), C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 alkoxycarbonyl, or C1-C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ (substituents in the text) Furthermore, R p With R s They can bond with each other to form a 5-6 membered ring with 0-2 atoms or groups selected from carbon atoms, oxygen atoms, and sulfur atoms (which may or may not be oxidized by one or two oxygen atoms), and the 5-6 membered ring may or may not be substituted by one or more chemically acceptable substituents selected from C1-C6 alkyl, C1-C6 alkoxy, or oxo groups. R u Indicates a hydrogen atom or a C1-C6 alkyl group. Substitute basis set α This indicates a halogen atom, hydroxyl group, mercapto group, amino group, cyano group, nitro group, C1-C6 alkyl group, C1-C6 haloalkyl group, or C3-C8 cycloalkyl group (the cycloalkyl group may or may not be selected from the substituent group). β Substituents in the group), C3-C8 halocycloalkyl groups (the halocycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1~C6 alkoxy, C1~C6 alkyl, C2~C6 alkenyl, C2~C6 ynyl, C3~C8 cycloalkyl, C2~C6 ynyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 alkoxy groups, C3-C8 cycloalkyloxy groups (the cycloalkyl group may or may not be selected from the substituent group) β Substituents in (C1-C6 alkyl oxy, C1-C6 alkoxy, C6-C6 alkoxy) 12 aryl C1-C6 alkoxy (the aryl group may or may not be substituted by one or more substituents selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, cyano), C2-C6 alkenoxy, C2-C6 alkynoxy, tris(C1-C6 alkyl)silyloxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ Substituents in (C1-C6 alkyl carbonyl amino groups) (the amino group may or may not be selected from the substituent group) γ (substituents in the group), C1-C6 alkyl carbonyl, C3-C8 cycloalkyl carbonyl (the cycloalkyl group may or may not be selected from the substituent group) β (substituents in the group), C1-C6 alkoxycarbonyl, aminocarbonyl, C1-C6 alkylaminocarbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl (the aryl group may or may not be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ Substituents in the group, substitution of one or more substituents in the cyano group, 5-12 membered heteroaryl groups (which are substituted or not substituted by one or more substituents selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino, di(C1-C6 alkyl)amino, cyano), oxo groups, or -C (=NR) m )R n base, Substitute basis set β This indicates a halogen atom, hydroxyl group, amino group, cyano group, C1-C6 alkyl group, C3-C8 cycloalkyl group (which may or may not be substituted by a substituent selected from C1-C6 alkyl or C1-C6 haloalkyl group), C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 alkyl group, C1-C6 alkoxy group, C1-C6 alkyl carbonyl amino group (which may or may not be selected from the substituent group) γ (substituents in the group), C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, amino carbonyl, C1-C6 alkylamino carbonyl (the amino group may or may not be selected from the substituent group) γ Substituents in (C6~C) 12 aryl (the aryl group may or may not be selected from halogen atoms, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino (the amino group may or may not be selected from the substituent group) γ The following groups may be substituted: (substituents in the group), one or more substituents in the cyano group), 5-12 membered heteroaryl groups (the heteroaryl group may or may not be substituted by one or more substituents selected from halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, C1-C6 alkylamino groups, di(C1-C6 alkyl)amino groups, or cyano groups), or 3-6 membered heterocyclic groups (the heterocyclic group may or may not be substituted by substituents selected from halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, or C1-C6 alkylamino groups (the amino group may or may not be substituted by substituents selected from the group consisting of halogen atoms, C1-C6 alkyl groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, amino groups, or C1-C6 alkylamino groups). γ (substituent substitution in the group), (substituent substitution of one or more substituents in the cyano group), Substitute basis set γ It represents C1~C6 alkyl, C1~C6 haloalkyl, C3~C8 cycloalkyl (which is substituted or not substituted by a substituent selected from C1~C6 alkyl or C1~C6 haloalkyl), C1~C6 alkoxy C1~C6 alkyl, C1~C6 haloalkyloxy C1~C6 alkyl, cyano C1~C6 alkyl carbonyl, C1~C6 haloalkyl carbonyl, or C1~C6 alkoxy carbonyl.

3. An agricultural and horticultural plant disease control agent, characterized in that, It contains the nicotinamide derivative or its salt as an active ingredient as described in claim 2.

4. The plant disease control agent for agricultural and horticultural use according to claim 1 or 3, wherein, Plant diseases originate from pathogenic fungi.

5. The plant disease control agent for agricultural and horticultural use according to claim 4, wherein, The plant diseases are classified into any of the following kingdoms: fungi, tegumentosa, foraminifera, and bacteria.

6. The plant disease control agent for agricultural and horticultural use according to claim 4, wherein, The plant diseases mentioned are classified as belonging to the Trichophyton genus.

7. An agricultural and horticultural plant disease control agent comprising the nicotinamide derivative or its salt as described in claim 2, and a pesticide-acceptable carrier.

8. A method for controlling plant diseases, comprising using an effective amount of the nicotinamide derivative of claim 2 or a salt thereof, by means of dispersal, soil application, surface application, seed treatment, soaking, poison bait or fumigation to control plant diseases.

9. The method according to claim 8, wherein, Distribute the seeds of useful plants or a portion thereof, or the place where the useful plants grow, or treat the seeds of useful plants.

10. The method according to claim 8, wherein, The plant diseases mentioned originate from pathogenic fungi.

11. The method according to claim 9, wherein, The plant diseases mentioned originate from pathogenic fungi.

12. The method according to claim 10, wherein, The plant diseases are classified into any of the following kingdoms: fungi, tegumentosa, foraminifera, and bacteria.

13. The method according to claim 11, wherein, The plant diseases are classified into any of the following kingdoms: fungi, tegumentosa, foraminifera, and bacteria.

14. The method of claim 10, wherein, The plant diseases mentioned are classified as belonging to the Trichophyton genus.

15. The method according to claim 11, wherein, The plant diseases mentioned are classified as belonging to the Trichophyton genus.

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

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