Heterocyclic compound and noxious arthropod control composition containing same

Abstract

The present invention provides a compound having an excellent controlling efficacy against harmful arthropods. (In the formula, the symbols have the meanings defined in the description. ) The compound or N-oxide thereof has an excellent controlling effect on harmful arthropods. # imgabs0 #

Description

Technical Field

[0001] This application claims priority and its benefits based on Japanese Patent Application No. 2022-177697 filed on November 4, 2022, Japanese Patent Application No. 2023-088026 filed on May 29, 2023, and Japanese Patent Application No. 2023-160980 filed on September 25, 2023, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a heterocyclic compound and a pest control composition containing the heterocyclic compound. Background Art

[0003] Hitherto, various compounds have been studied for the purpose of controlling harmful arthropods. For example, Patent Document 1 describes that a certain compound has a pest control effect.

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: WO 2016 / 129684 Summary of the Invention

[0007] Problems to be Solved by the Invention

[0008] The problem of the present invention is to provide a compound having excellent control efficacy against harmful arthropods.

[0009] Means for Solving the Problems

[0010] The present invention is as follows.

[0011] [1] A compound represented by formula (I) (hereinafter referred to as Compound N of the present invention) or its N-oxide (hereinafter, the compound represented by formula (I) or its N-oxide is referred to as the compound of the present invention).

[0012] [Chemical Formula 1]

[0013]

[0014] [In the formula,

[0015] Q represented by the following formula (where # represents the bonding site to the sulfur atom and ● represents the bonding site to Het) represents a group represented by formula Q1 or a group represented by formula Q2,

[0016] [Chemical Formula 2]

[0017]

[0018] [Chemical Formula 3]

[0019]

[0020] A 1 Represents nitrogen atom or CR 8 ,

[0021] R 8 represents a halogen atom or a hydrogen atom,

[0022] R 2 represents a C1-C6 alkyl group, a cyclopropyl group, or a cyclopropylmethyl group which may be substituted with one or more halogen atoms,

[0023] n represents 0, 1 or 2,

[0024] G 1 Represents nitrogen atom or CR 3a ,

[0025] G 2 Represents nitrogen atom or CR 3b ,

[0026] G 3 Represents nitrogen atom or CR 3c ,

[0027] G 4 Represents nitrogen atom or CR 3d ,

[0028] R 3a , R 3b , R 3c and R 3d are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group L, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group E, a phenyl group which may be substituted by one or more substituents selected from group H, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group H, OR 12 NR 11 R 12 NR 11a R 12a NR 24 NR 11 R 12 NR 24 OR 11 NR 11 C(O)R 13 NR 24 NR 11 C(O)R 13 NR 11 C(O)OR 14 NR 24 NR11 C(O)OR 14 、NR 11 C(O)NR 31 R 32 、NR 24 NR 11 C(O)NR 31 R 32 、N=CHNR 31 R 32 、N=S(O) p R 15 R 16 、C(O)R 13 、C(O)OR 17 、C(O)NR 31 R 32 、C(O)NR 11 S(O)2R 23 、CR 30 =NOR 17 、NR 11 CR 24 =NOR 17 、S(O) m R 23 、 a cyano group, a nitro group, a halogen atom or a hydrogen atom,

[0029] p represents 0 or 1,

[0030] m represents 0, 1 or 2,

[0031] R 30 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a halogen atom, OR 35 、NR 36 R 37 or a hydrogen atom,

[0032] R 35 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms,

[0033] R 17 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from group D, or a hydrogen atom,

[0034] R 11 、R 24 、R 36 and R 37 are the same as or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom,

[0035] R 12represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group F, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group J, a C3-C7 cycloalkenyl group which may be substituted by one or more substituents selected from group J, a phenyl group which may be substituted by one or more substituents selected from group D, a 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group D, S(O)2R 23 or a hydrogen atom,

[0036] R 23 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a phenyl group which may be substituted by one or more substituents selected from group D,

[0037] R 11a and R 12a together with the nitrogen atom to which they are attached form a 3-7 membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from group E,

[0038] R 13 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group D, or a hydrogen atom,

[0039] R 14 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, or a phenylC1-C3 alkyl group {the phenyl moiety in the phenylC1-C3 alkyl group may be substituted by one or more substituents selected from group D},

[0040] R 15 and R 16 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms,

[0041] R 31 represents a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a hydrogen atom,

[0042] R 32 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group F, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group J, S(O)2R 23 or a hydrogen atom,

[0043] R 4Represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group L 2 a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group E 2 a phenyl group which may be substituted by one or more substituents selected from group H 2 a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group H 2 OR 42 NR 41 R 42 NR 41a R 42a NR 54 NR 41 R 42 NR 54 OR 41 NR 41 C(O)R 43 NR 54 NR 41 C(O)R 43 NR 41 C(O)OR 44 NR 54 NR 41 C(O)OR 44 NR 41 C(O)NR 61 R 62 NR 54 NR 41 C(O)NR 61 R 62 N=CHNR 61 R 62 N=S(O) r R 45 R 46 C(O)R 43 C(O)OR 47 C(O)NR 61 R 62 C(O)NR 41 S(O)2R 53 CR 60 =NOR 47 NR 41 CR 54 =NOR 47 S(O) t R 53 a cyano group, a nitro group or a halogen atom,

[0044] r represents 0 or 1,

[0045] t represents 0, 1 or 2,

[0046] R 60 represents a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a halogen atom, OR 65 NR 66 R 67 or a hydrogen atom,

[0047] R 65 represents a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms,

[0048] R 47 represents a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a phenyl group that may be substituted by one or more substituents selected from group D 2 or a hydrogen atom,

[0049] R 41 R 54 R 66 and R 67 are the same or different from each other and represent a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms or a hydrogen atom,

[0050] R 42 represents a C1-C6 chain hydrocarbon group that may be substituted by one or more substituents selected from group F 2 a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from group J 2 a C3-C7 cycloalkenyl group that may be substituted by one or more substituents selected from group J 2 a phenyl group that may be substituted by one or more substituents selected from group D 2 a 6-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from group D 2 a hydrogen atom or S(O)2R 53 ,

[0051] R 53 represents a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms or a phenyl group that may be substituted by one or more substituents selected from group D 2 ,

[0052] R 41a and R 42a together with the nitrogen atom to which they are bonded form a 3-7 membered non-aromatic heterocyclic group that may be substituted by one or more substituents selected from group E 2 ,

[0053] R 43 represents a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that may be substituted by one or more halogen atoms, a phenyl group that may be substituted by one or more substituents selected from group D2 phenyl substituted with one or more substituents in, or a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents selected from Group D 2 or a hydrogen atom,

[0054] R 44 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenylC1-C3 alkyl group {the phenyl moiety in the phenylC1-C3 alkyl group may be substituted with one or more substituents selected from Group D 2}

[0055] R 45 and R 46 are the same as or different from each other and represent a C1-C6 alkyl group which may be substituted with one or more halogen atoms,

[0056] R 61 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms or a hydrogen atom,

[0057] R 62 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F 2 or a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from Group J 2 or S(O)2R 53 or a hydrogen atom,

[0058] k represents 0, 1, 2 or 3, and when k is 2 or 3, the two or three Rs 4 may be the same or different,

[0059] When two Rs 4 are bonded to adjacent carbon atoms, the two Rs 4 may together with the two carbon atoms to which they are bonded form a benzene ring, a pyrrole ring, a furan ring, a thiophene ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring or a pyrazine ring {the benzene ring, the pyrrole ring, the furan ring, the thiophene ring, the pyrazole ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the pyridine ring, the pyridazine ring, the pyrimidine ring and the pyrazine ring may be substituted with one or more substituents selected from Group H 2} or a triazole ring which may be substituted with one or more substituents selected from Group P,

[0060] Het represents a group represented by Formula Het1 or a group represented by Formula Het2,

[0061] [Chemical Formula 4]

[0062]

[0063] A 2 represents -NR 5a -, or -CR 7a R 7b -,

[0064] A 3 represents -CR 7c R 7d -, -CR 7e R 7f -CR 7g R 7h -* 1 、or -CR 7i R 7j -CR 7k R 7l -CR 7m R 7n -* 1 ,

[0065] * 1 represents the bonding position with A 2 ,

[0066] A 4 represents -NR 5b -, -CR 7o R 7p -, -CR 7q R 7r -CR 7s R 7t -* 2 、-NR 5c -CR 7u R 7v -* 2 、-CR 7w R 7x -CR 7y R 7z -CR 7aa R 7bb -* 2 、or -NR 5d -CR 7cc R 7dd -CR 7ee R 7ff -* 2 ,

[0067] * 2 represents the bonding position with A 2 ,

[0068] R 5a 、R 5b 、R 5c and R5d are the same as or different from each other, and represent a C1-C6 chain hydrocarbon group that may be substituted by one or more substituents selected from group K, a C1-C6 alkoxy group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C6 alkyl group that may be substituted by one or more halogen atoms, or a hydrogen atom,

[0069] R 7a 、R 7b 、R 7c 、R 7d 、R 7e 、R 7f 、R 7g 、R 7h 、R 7i 、R 7j 、R 7k 、R 7l 、R 7m 、R 7n 、R 7o 、R 7p 、R 7q 、R 7r 、R 7s 、R 7t 、R 7u 、R 7v 、R 7w 、R 7x 、R 7y 、R 7z 、R 7aa 、R 7bb 、R 7cc 、R 7dd 、R 7ee and R 7ff are the same as or different from each other, and represent a C1-C6 chain hydrocarbon group that may be substituted by one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C4 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of a cyano group and a halogen atom, a nitro group, OR 69 、NR 69 R 70 、a cyano group, a halogen atom or a hydrogen atom,

[0070] R 7a and R 7b 、R 7c and R 7d 、R 7e and R 7f 、R 7g and R 7h 、R 7i and R 7j 、R 7k and R 7l 、R 7mand R 7n , R 7o and R 7p , R 7q and R 7r , R 7s and R 7t , R 7u and R 7v , R 7w and R 7x , R 7y and R 7z , R 7aa and R 7bb , R 7cc and R 7dd , and R 7ee and R 7ff Each may form, together with the carbon atom to which they are bonded, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom,

[0071] R 69 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group T, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group U, a C3-C7 cycloalkenyl group which may be substituted by one or more substituents selected from group U, a phenyl group which may be substituted by one or more substituents selected from group V, a 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group V, or a hydrogen atom,

[0072] R 70 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a hydrogen atom,

[0073] W represents an oxygen atom or a sulfur atom,

[0074] B 1 Represents CR 6a or nitrogen atoms,

[0075] B 2 Represents CR 6b or nitrogen atoms,

[0076] B 3 Represents CR 6c or nitrogen atoms,

[0077] R 6a , R 6b and R 6c The same or different from each other, indicating that they can be selected from the group L 3 A C1-C6 chain hydrocarbon group substituted with one or more substituents, which may be selected from Group E 3 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from Group H 3phenyl substituted with one or more substituents selected from the group H 3 a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents selected from the group H, OR 72 NR 71 R 72 NR 71a R 72a NR 84 NR 71 R 72 NR 84 OR 71 NR 71 C(O)R 73 NR 84 NR 71 C(O)R 73 NR 71 C(O)OR 74 NR 84 NR 71 C(O)OR 74 NR 71 C(O)NR 91 R 92 NR 84 NR 71 C(O)NR 91 R 92 N=CHNR 91 R 92 N=S(O) q R 75 R 76 C(O)R 73 C(O)OR 77 C(O)NR 91 R 92 C(O)NR 71 S(O)2R 83 CR 90 =NOR 77 NR 71 CR 84 =NOR 77 S(O) v R 83 a cyano group, a nitro group, a halogen atom or a hydrogen atom,

[0078] q represents 0 or 1,

[0079] v represents 0, 1 or 2,

[0080] R 90 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a halogen atom, OR 95 NR 96 R 97 or a hydrogen atom,

[0081] R 95 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms,

[0082] R 77 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group D 3 or a hydrogen atom,

[0083] R 71 R 84 R 96 and R 97 are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms or a hydrogen atom,

[0084] R 72 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group F 3 a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from Group J 3 a C3-C7 cycloalkenyl group which may be substituted by one or more substituents selected from Group J 3 a phenyl group which may be substituted by one or more substituents selected from Group D 3 a 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group D 3 S(O)2R 83 or a hydrogen atom,

[0085] R 83 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms or a phenyl group which may be substituted by one or more substituents selected from Group D 3 and

[0086] R 71a and R 72a together with the nitrogen atom to which they are attached form a 3-7 membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from Group E 3 and

[0087] R 73 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group D 3 or a hydrogen atom,

[0088] R 74Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that can be substituted by one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group can be substituted by one or more substituents selected from group D 3}

[0089] R 75 and R 76 are the same or different from each other and represent a C1-C6 alkyl group that can be substituted by one or more halogen atoms,

[0090] R 91 represents a C1-C6 alkyl group that can be substituted by one or more halogen atoms, or a hydrogen atom,

[0091] R 92 represents a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F 3}, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from group J 3}, S(O)2R 83 or a hydrogen atom.

[0092] Group L: A group consisting of a C1-C6 alkoxy group that can be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group that can be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group that can be substituted by one or more halogen atoms, a C1-C6 alkylthio group that can be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group that can be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group that can be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted by one or more halogen atoms, a cyano group, a hydroxyl group, and a halogen atom.

[0093] Group M: A group consisting of a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C6 alkoxy group that can be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group that can be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group that can be substituted by one or more halogen atoms, and a halogen atom.

[0094] Group D: Consisting of a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group that can be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group that can be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group that can be substituted by one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group that can be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group that can be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group that can be substituted by one or more halogen atoms, an amino group, NHR 21, NR 21 R 22 , C(O)R 21 , OC(O)R 21 , C(O)OR 21 , a group consisting of a cyano group, a nitro group and a halogen atom.

[0095] R 21 and R 22 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms.

[0096] Group E: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group.

[0097] Group F: a group consisting of a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from Group M, an amino group, NHR 21 , NR 21 R 22 , a group consisting of a halogen atom and a cyano group.

[0098] Group H: a group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, OR 10 , NR 9 R 10 , C(O)R 10 , C(O)NR 9 R 10 , OC(O)R 9 , OC(O)OR 9 , NR 10 C(O)R 9 , NR 10 C(O)OR 9 , C(O)OR 10 , a group consisting of a halogen atom, a nitro group, a cyano group, an amino group and a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group W.

[0099] R 9 represents a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms,

[0100] R10 Represents a C1-C6 alkyl group that may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or more halogen atoms, or a hydrogen atom.

[0101] Group P: Consists of a C2-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or more halogen atoms, a phenyl group that may be substituted with one or more substituents selected from Group D 2 among them, a 5- or 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from Group D 2 among them, a C2-C6 alkylcarbonyl group that may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group that may be substituted with one or more halogen atoms, an aminocarbonyl group, a (C1-C6 alkyl)aminocarbonyl group that may be substituted with one or more halogen atoms, a methyl group, and a di(C1-C4 alkyl)aminocarbonyl group that may be substituted with one or more halogen atoms.

[0102] Group J: Consists of a C1-C6 alkyl group that may be substituted with one or more halogen atoms, a halogen atom, and a cyano group.

[0103] Group K: Consists of a C1-C6 alkoxy group that may be substituted with one or more halogen atoms, a phenyl group that may be substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from Group D, a C3-C7 cycloalkyl group that may be substituted with one or more halogen atoms, and a 3-7 membered non-aromatic heterocyclic group that may be substituted with one or more substituents selected from Group M.

[0104] Group T: Consists of a C1-C6 alkoxy group that may be substituted with one or more halogen atoms, a phenyl group that may be substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from Group D, a C3-C7 cycloalkyl group that may be substituted with one or more halogen atoms, a 3-7 membered non-aromatic heterocyclic group that may be substituted with one or more substituents selected from Group M, an amino group, NHR 21 、NR 21 R 22 、R, a halogen atom, and a cyano group.

[0105] Group U: Consists of a C1-C6 alkyl group that may be substituted with one or more halogen atoms, a halogen atom, and a cyano group.

[0106] Group V: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group and a halogen atom.

[0107] Group W: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group and a halogen atom.

[0108] Group L 2 : a group consisting of a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, a cyano group, a hydroxyl group and a halogen atom.

[0109] Group D 2: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group and a halogen atom.

[0110] Group E 2 : a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group.

[0111] Group F 2 : a group consisting of a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a 3-7 membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from Group M, an amino group, NHR 21 、NR 21 R 22 、a halogen atom and a cyano group.

[0112] Group H 2 : a group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, OR 10 、NR 9 R 10 、C(O)R 10 、C(O)NR 9 R 10 、OC(O)R 9 、OC(O)OR 9 、NR 10 C(O)R 9 、NR 10 C(O)OR 9 、C(O)OR 10A group consisting of a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group W.

[0113] Group J 2 : A group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a halogen atom, and a cyano group.

[0114] Group L 3 : A group consisting of a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylthio group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom.

[0115] Group D 3 : A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group, and a halogen atom.

[0116] Group E 3 : A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group.

[0117] Group F 3: A group consisting of a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a 3-7 membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from Group M, an amino group, NHR 21 , NR 21 R 22 , a halogen atom and a cyano group.

[0118] Group H 3 : A group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, OR 10 , NR 9 R 10 , C(O)R 10 , C(O)NR 9 R 10 , OC(O)R 9 , OC(O)OR 9 , NR 10 C(O)R 9 , NR 10 C(O)OR 9 , C(O)OR 10 , a halogen atom, a nitro group, a cyano group, an amino group and a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group W.

[0119] Group J 3 : A group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a halogen atom and a cyano group. ]]

[0120] [2] The compound or its N-oxide according to [1], wherein Q is a group represented by formula Q1.

[0121] [3] The compound or its N-oxide according to [1], wherein Q is a group represented by formula Q2.

[0122] [4] The compound or its N-oxide according to [1], wherein Q is a group represented by formula Q1, and G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom or CR 3d .

[0123] [5] The compound or its N-oxide according to [1], wherein Q is a group represented by formula Q1, and G 1 is CR 3a, G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d .

[0124] 〔6〕The compound or its N-oxide as described in 〔1〕, wherein Q is a group represented by formula Q2, and A 1 is a nitrogen atom.

[0125] 〔7〕The compound or its N-oxide as described in 〔1〕, wherein Q is a group represented by formula Q2, and A 1 is CR 8 .

[0126] 〔8〕The compound or its N-oxide as described in any one of 〔1〕 to 〔7〕, wherein Het is a group represented by formula Het1, and A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d - or -CR 7e R 7f -CR 7g R 7h -* 1 , and W is an oxygen atom.

[0127] 〔9〕The compound or its N-oxide as described in any one of 〔1〕 to 〔7〕, wherein Het is a group represented by formula Het2, and A 2 is -CR 7a R 7b -, A 4 is -CR 7o R 7p - or -CR 7q R 7r -CR 7s R 7t -* 2 , and W is an oxygen atom.

[0128] 〔10〕A pest arthropod control composition comprising an inert carrier and the compound or its N-oxide as described in any one of 〔1〕 to 〔9〕.

[0129] 〔11〕A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound or its N-oxide as described in any one of 〔1〕 to 〔9〕,

[0130] Group (a): The group consisting of an insecticidal active ingredient, a miticidal active ingredient and a nematicidal active ingredient;

[0131] Group (b): bactericidal active ingredient;

[0132] Group (c): plant growth regulating ingredient;

[0133] Group (d): repellent ingredient.

[0134] 〔12〕Method for controlling harmful arthropods, wherein an effective amount of the compound or its N-oxide as described in any one of 〔1〕 to 〔9〕 or an effective amount of the composition as described in 〔11〕 is applied to harmful arthropods or their habitats.

[0135] 〔13〕Seeds or vegetative propagation organs which hold an effective amount of the compound or its N-oxide as described in any one of 〔1〕 to 〔9〕 or an effective amount of the composition as described in 〔11〕.

[0136] 〔14〕Compound represented by formula (II) or its salt (hereinafter, the compound represented by formula (II) or its salt is referred to as intermediate A).

[0137] [Chemical formula 5]

[0138]

[0139] 〔In the formula, X 1 represents a chlorine atom, a bromine atom, an iodine atom or a hydroxyl group, and other symbols represent the same meanings as in 〔1〕.〕

[0140] 〔15〕Compound represented by formula (III) or its salt (hereinafter, the compound represented by formula (III) or its salt is referred to as intermediate B).

[0141] [Chemical formula 6]

[0142]

[0143] 〔In the formula, X 2 represents a chlorine atom, a bromine atom, an iodine atom or a hydroxyl group, and other symbols represent the same meanings as in 〔1〕.〕

[0144] Advantages of the Invention

[0145] By the present invention, harmful arthropods can be controlled. Detailed Description of the Invention

[0146] The substituents in the present invention are described.

[0147] The halogen atom means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0148] When the substituent is substituted by two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different from each other.

[0149] The expression "CX-CY" in this specification means that the number of carbon atoms is from X to Y. For example, the expression "C1-C6" means that the number of carbon atoms is from 1 to 6.

[0150] The so-called chain hydrocarbon group means an alkyl group, an alkenyl group or an alkynyl group.

[0151] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group and a hexyl group.

[0152] Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group, a 1-ethyl-2-propenyl group, a 3-butenyl group, a 4-pentenyl group and a 5-hexenyl group.

[0153] Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 1-ethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group and a 5-hexynyl group.

[0154] Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group and a hexyloxy group.

[0155] Examples of the alkenyloxy group include a 2-propenyloxy group, a 2-butenyloxy group and a 5-hexenyloxy group.

[0156] Examples of the alkynyloxy group include a 2-propynyloxy group, a 2-butynyloxy group and a 5-hexynyloxy group.

[0157] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cycloheptyl group.

[0158] Examples of the cycloalkenyl group include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group and a cycloheptenyl group.

[0159] Examples of the 3- to 7-membered non-aromatic heterocyclic group include, for example, aziridinyl, oxiranyl, thiiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuryl, tetrahydrothienyl, piperidinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothianyl, azepanyl, oxepanyl, thiepanyl, pyrazolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, thiazolinyl, oxazolidinyl, thiazolidinyl, isoxazolinyl, isoxazolidinyl, isothiazolinyl, isothiazolidinyl, dioxolanyl, dioxolyl, dioxanyl, morpholinyl, thiomorpholinyl, and piperazinyl.

[0160] Examples of the 5- or 6-membered aromatic heterocyclic group include, for example, pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetrazinyl.

[0161] Examples of the 6-membered aromatic heterocyclic group include, for example, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetrazinyl.

[0162] Examples of the (C3-C6 cycloalkyl)C1-C3 alkyl which may be substituted with one or more halogen atoms include, for example, cyclopropylmethyl, (2-fluorocyclopropyl)methyl, cyclopropyl(fluoro)methyl, and (2-fluorocyclopropyl)(fluoro)methyl.

[0163] The (C3-C7 cycloalkyl)C1-C6 alkyl which may be substituted with one or more halogen atoms means a group in which the (C3-C7 cycloalkyl) and / or the (C1-C6 alkyl) may be substituted with one or more halogen atoms, and examples thereof include (2,2-difluorocyclopropyl)methyl, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl, 2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl, (2,2-difluorocyclopropyl)propyl, (2,2-difluorocyclopropyl)butyl, (2,2-difluorocyclopropyl)pentyl, and (2,2-difluorocyclopropyl)hexyl.

[0164] Examples of the phenyl C1-C3 alkyl {the phenyl moiety in the phenyl C1-C3 alkyl may be substituted with one or more substituents selected from Group D}, phenyl C1-C3 alkyl {the phenyl moiety in the phenyl C1-C3 alkyl may be substituted with one or more substituents selected from Group D 2 in}, and phenyl C1-C3 alkyl {the phenyl moiety in the phenyl C1-C3 alkyl may be substituted with one or more substituents selected from Group D 3 in} include, for example, benzyl, 2-fluorobenzyl, 4-chlorobenzyl, 4-(trifluoromethyl)benzyl, and 2-[4-(trifluoromethyl)phenyl]ethyl.

[0165] Examples of the alkylthio group include methylthio, ethylthio, propylthio, and isopropylthio.

[0166] Examples of the alkylsulfinyl group include methylsulfinyl, ethylsulfinyl, propylsulfinyl, and isopropylsulfinyl.

[0167] Examples of the alkylsulfonyl group include methylsulfonyl, ethylsulfonyl, propylsulfonyl, and isopropylsulfonyl.

[0168] Examples of the alkylcarbonyl group include acetyl, propionyl, 2-methylpropionyl, and hexanoyl.

[0169] Examples of the alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, and pentyloxycarbonyl.

[0170] Examples of the (C1-C6 alkyl)aminocarbonyl group which may be substituted with one or more halogen atoms include methylaminocarbonyl, trifluoromethylaminocarbonyl, isopropylaminocarbonyl, and hexylaminocarbonyl.

[0171] Examples of the bis(C1-C4 alkyl)aminocarbonyl group which may be substituted with one or more halogen atoms include dimethylaminocarbonyl, methylethylaminocarbonyl, trifluoromethylethylaminocarbonyl, and diisopropylaminocarbonyl.

[0172] Examples of the N-oxide of the compound represented by the formula (I) include the compounds represented by the following formula.

[0173] [Chemical formula 7]

[0174]

[0175] [In the formula, the symbol represents the same meaning as described above.]

[0176] The compounds of the present invention may have one or more stereoisomers. Examples of the stereoisomers include enantiomers, diastereomers, and geometric isomers. The compounds of the present invention include each stereoisomer and a mixture of stereoisomers in any ratio.

[0177] The compounds of the present invention, the compounds represented by the formula (II), and the compounds represented by the formula (III) may form acid addition salts. Examples of the acid for forming the acid addition salts include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid. The acid addition salts can be obtained by mixing the compounds of the present invention, the compounds represented by the formula (II), or the compounds represented by the formula (III) with an acid.

[0178] Examples of the compounds of the present invention in the form of N include the following compounds.

[0179] 〔Mode 1〕Among the compounds of the present invention N, the compound in which W is an oxygen atom.

[0180] 〔Mode 2〕Among the compounds of the present invention N, R 2 is a C1-C6 alkyl group.

[0181] 〔Mode 3〕Among the compounds of the present invention N, R 2 is an ethyl group.

[0182] 〔Mode 4〕Among the compounds of the present invention N, the compound in which Q is the group represented by Q1.

[0183] 〔Mode 5〕Among the compounds of the present invention N, the compound in which Q is the group represented by Q2.

[0184] 〔Mode 6〕Among the compounds of the present invention N, the compound in which Het is the group represented by Het1.

[0185] 〔Mode 7〕Among the compounds of the present invention N, the compound in which Het is the group represented by Het2.

[0186] 〔Mode 8〕Among the compounds of the present invention N, Q is the group represented by Q1, and the combinations of G 1 , G 2 , G 3 and G 4 are: G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom; G 1 is CR 3a , G 2 is CR 3b , G 3 is a nitrogen atom, G 4 is CR 3d ; G 1 is CR 3a , G 2 is a nitrogen atom, G 3 is CR 3c , G 4 is CR 3d ; G 1 is a nitrogen atom, G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d ; or G 1 is CR 3a 、G2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d in combination, R 3a and R 3c and R 3d is a hydrogen atom, and R 3b is a C1-C6 alkyl group that may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups, a phenyl group that may be substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group that may be substituted with one or more halogen atoms, or a compound of a halogen atom.

[0187] 〔Mode 9〕In the compound N of the present invention, Q is the group represented by Q1, and G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a and R 3c and R 3d is a hydrogen atom, and R 3b is a C1-C6 alkyl group that may be substituted with one or more halogen atoms, or a compound of a halogen atom.

[0188] 〔Mode 10〕In the compound N of the present invention, Q is the group represented by Q1, and G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a and R 3c and R 3d is a hydrogen atom, and R 3b is a C1-C6 alkyl group that may be substituted with one or more halogen atoms, or a compound of a halogen atom.

[0189] 〔Mode 11〕In the compound N of the present invention, Q is the group represented by Q1, and G 1 and G 2 and G 3 and G 4 The combination of is: G 1 is CR 3a and G 2 is CR 3b and G 3For CR 3c and G 4 is a combination of nitrogen atoms; G 1 For CR 3a and G 2 For CR 3b and G 3 is a nitrogen atom, G 4 For CR 3d and G 1 For CR 3a and G 2 is a nitrogen atom, G 3 For CR 3c and G 4 For CR 3d and G 1 is a nitrogen atom, G 2 For CR 3b and G 3 For CR 3c and G 4 For CR 3d and G 1 For CR 3a and G 2 For CR 3b and G 3 For CR 3c and G 4 For CR 3d and R 3a and R 3b and R 3d are hydrogen atoms, and R 3c is a halogen atom compound.

[0190] 〔Mode 12〕In the compound N of the present invention, Q is the group shown by Q1, and G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a and R 3b and R 3d are hydrogen atoms, and R 3c is a halogen atom compound.

[0191] 〔Mode 13〕In the compound N of the present invention, Q is the group shown by Q1, and G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR3d , R 3a , R 3b and R 3d is a hydrogen atom, R 3c A compound containing halogen atoms.

[0192] [Form 14] In the compound N of the present invention, Q is a group represented by Q2, A 1 A compound containing nitrogen atoms.

[0193] [Form 15] In the compound N of the present invention, Q is a group represented by Q2, A 1 CR 8 of compounds.

[0194] [Form 16] In the compound N of the present invention, Q is a group represented by Q2, and R 4 can be selected from group E 2 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from Group H 2 The phenyl group substituted with one or more substituents in the group H 2 A compound containing a 5- or 6-membered aromatic heterocyclic group, a halogen atom or a hydrogen atom substituted with one or more substituents.

[0195] [Form 17] In the compound N of the present invention, Q is a group represented by Q2, A 1 is a nitrogen atom or CR 8 , k is 2, 2 R 4 Adjacent, and 2 R 4 Together with the two carbon atoms to which they are bonded, they form a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring or a pyrazine ring {the benzene ring, the pyridine ring, the pyridazine ring, the pyrimidine ring and the pyrazine ring can be selected from the group H 2 The compound is substituted with one or more substituents in .

[0196] [Form 18] In the compound N of the present invention, Q is a group represented by Q2, and R 4 can be selected from group E 2 C3-C7 cycloalkyl substituted with one or more substituents, which may be selected from Group H 2 The phenyl group substituted with one or more substituents in the group H 2 A compound containing a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, or a halogen atom.

[0197] [Embodiment 19] In the compound N of the present invention, G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G4 is CR 3d , R 3a 、R 3c and R 3d are hydrogen atoms, R 3b is a halogen atom, A 1 is a nitrogen atom, k is 0 or 1, R 4 is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group or a halogen atom compound.

[0198] 〔Mode 20〕In the compound N of the present invention, Q is a group represented by Q1, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d , R 3a 、R 3c and R 3d are hydrogen atoms, R 3b is a halogen atom compound.

[0199] 〔Mode 21〕In the compound N of the present invention, Q is a group represented by Q2, A 1 is a nitrogen atom, k is 0 or 1, R 4 is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group or a halogen atom compound.

[0200] 〔Mode 22〕In the compound N of the present invention, Q is a group represented by Q2, A 1 is a nitrogen atom, k is 0 or 1, R 4 is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, or a pyrimidinyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom compound.

[0201] 〔Mode 23〕In the compound N of the present invention, Q is a group represented by Q2, A 1 is a nitrogen atom, k is 0 or 1, R 4A compound which is a phenyl group substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, or a pyridyl group substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom.

[0202] 〔Embodiment 24〕In the compound N of the present invention, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d , R 3a , R 3c and R 3d are hydrogen atoms, R 3b is a halogen atom, A 1 is a nitrogen atom, k is 0 or 1, and R 4 is a phenyl group substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, OR 42 , NR 41 R 42 , NR 41 C(O)R 43 , NR 41 C(O)OR 44 or a halogen atom.

[0203] 〔Embodiment 25〕In the compound N of the present invention, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d , R 3a , R 3c and R 3d are hydrogen atoms, R 3b is a halogen atom, A 1 is a nitrogen atom, k is 0 or 1, and R 4 is a phenyl group substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR 42 , NR 41 R 42 , NR 41 C(O)R 43 , or NR 41 C(O)OR 44 , R41 is a C1-C6 alkyl group or a hydrogen atom, R 42 is a hydrogen atom, R 43 is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, R 44 is a compound of a C1-C6 alkyl group.

[0204] 〔Mode 26〕In the compound N of the present invention, Q is a group represented by Q2, A 1 is a nitrogen atom, k is 0 or 1, R 4 is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, OR 42 、NR 41 R 42 、NR 41 C(O)R 43 、NR 41 C(O)OR 44 or a halogen atom.

[0205] 〔Mode 27〕In the compound N of the present invention, Q is a group represented by Q2, A 1 is a nitrogen atom, k is 0 or 1, R 4 is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR 42 、NR 41 R 42 、NR 41 C(O)R 43 、or NR 41 C(O)OR 44 ,R 41 is a C1-C6 alkyl group or a hydrogen atom, R 42 is a hydrogen atom, R 43 is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, R 44 is a compound of a C1-C6 alkyl group.

[0206] 〔Mode 28〕In the compound N of the present invention, Q is a group represented by Q1 or a group represented by formula Q2a, G 1 is CR 3a ,G 2 is CR 3b ,G 3 is CR 3c ,G 4 is CR 3d ,R 3a 、R 3c and R 3dis a hydrogen atom, R 3b is a halogen atom, A 1 is a nitrogen atom, ka is 0 or 1, R 4b is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, OR 42 、NR 41 R 42 、NR 41 C(O)R 43 、NR 41 C(O)OR 44 or a compound of a halogen atom.

[0207] [Chemical Formula 8]

[0208]

[0209] [Aspect 29] In the compound N of the present invention, Q is a group represented by Q1 or a group represented by the above formula Q2a, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d , R 3a 、R 3c and R 3d are hydrogen atoms, R 3b is a halogen atom, A 1 is a nitrogen atom, ka is 0 or 1, R 4b is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR 42 、NR 41 R 42 、NR 41 C(O)R 43 、or NR 41 C(O)OR 44 , R 41 is a C1-C6 alkyl group or a hydrogen atom, R 42 is a hydrogen atom, R 43 is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, R 44 is a compound of a C1-C6 alkyl group.

[0210] [Aspect 30] In the compound N of the present invention, Q is a group represented by the above formula Q2a, A 1is a nitrogen atom, ka is 0 or 1, R 4b is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, OR 42 、NR 41 R 42 、NR 41 C(O)R 43 、NR 41 C(O)OR 44 or a compound of a halogen atom.

[0211] 〔Mode 31〕In the compound N of the present invention, Q is a group represented by the above formula Q2a, A 1 is a nitrogen atom, ka is 0 or 1, R 4b is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR 42 、NR 41 R 42 、NR 41 C(O)R 43 、or NR 41 C(O)OR 44 ,R 41 is a C1-C6 alkyl group or a hydrogen atom, R 42 is a C1-C6 alkyl group which may be substituted with one or more halogen atoms or a hydrogen atom, R 43 is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, R 44 is a compound of a C1-C6 alkyl group.

[0212] 〔Mode 32〕In the compound N of the present invention, Q is a group represented by the above formula Q2a, A 1 is a nitrogen atom, ka is 0 or 1, R 4b is a phenyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR 42 、NR 41 R 42 、NR 41 C(O)R 43 、or NR 41 C(O)OR 44 ,R 41 is a C1-C6 alkyl group or a hydrogen atom, R 42 is a hydrogen atom, R 43 is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, R 44A compound that is a C1-C6 alkyl group.

[0213] 〔Mode 33〕In Mode 2, a compound where W is an oxygen atom.

[0214] 〔Mode 34〕In Mode 3, a compound where W is an oxygen atom.

[0215] 〔Mode 35〕In Mode 4, a compound where W is an oxygen atom.

[0216] 〔Mode 36〕In Mode 5, a compound where W is an oxygen atom.

[0217] 〔Mode 37〕In Mode 6, a compound where W is an oxygen atom.

[0218] 〔Mode 38〕In Mode 7, a compound where W is an oxygen atom.

[0219] 〔Mode 39〕In Mode 8, a compound where W is an oxygen atom.

[0220] 〔Mode 40〕In Mode 9, a compound where W is an oxygen atom.

[0221] 〔Mode 41〕In Mode 10, a compound where W is an oxygen atom.

[0222] 〔Mode 42〕In Mode 11, a compound where W is an oxygen atom.

[0223] 〔Mode 43〕In Mode 12, a compound where W is an oxygen atom.

[0224] 〔Mode 44〕In Mode 13, a compound where W is an oxygen atom.

[0225] 〔Mode 45〕In Mode 14, a compound where W is an oxygen atom.

[0226] 〔Mode 46〕In Mode 15, a compound where W is an oxygen atom.

[0227] 〔Mode 47〕In Mode 16, a compound where W is an oxygen atom.

[0228] 〔Mode 48〕In Mode 17, a compound where W is an oxygen atom.

[0229] 〔Mode 49〕In Mode 18, a compound where W is an oxygen atom.

[0230] 〔Mode 50〕In Mode 19, a compound where W is an oxygen atom.

[0231] 〔Mode 51〕In Mode 20, a compound where W is an oxygen atom.

[0232] 〔Mode 52〕In Mode 21, a compound where W is an oxygen atom.

[0233] [Mode 53] In Mode 22, a compound where W is an oxygen atom.

[0234] [Mode 54] In Mode 23, a compound where W is an oxygen atom.

[0235] [Mode 55] In Mode 24, a compound where W is an oxygen atom.

[0236] [Mode 56] In Mode 25, a compound where W is an oxygen atom.

[0237] [Mode 57] In Mode 26, a compound where W is an oxygen atom.

[0238] [Mode 58] In Mode 27, a compound where W is an oxygen atom.

[0239] [Mode 59] In Mode 28, a compound where W is an oxygen atom.

[0240] [Mode 60] In Mode 29, a compound where W is an oxygen atom.

[0241] [Mode 61] In Mode 30, a compound where W is an oxygen atom.

[0242] [Mode 62] In Mode 31, a compound where W is an oxygen atom.

[0243] [Mode 63] In Mode 32, a compound where W is an oxygen atom.

[0244] [Mode 64] In Mode 4, R 2 is a C1-C6 alkyl compound. [Mode 65] In Mode 5, R 2 is a C1-C6 alkyl compound. [Mode 66] In Mode 6, R 2 is a C1-C6 alkyl compound. [Mode 67] In Mode 7, R 2 is a C1-C6 alkyl compound. [Mode 68] In Mode 8, R 2 is a C1-C6 alkyl compound. [Mode 69] In Mode 9, R 2 is a C1-C6 alkyl compound. [Mode 70] In Mode 10, R 2 is a C1-C6 alkyl compound. [Mode 71] In Mode 11, R 2 is a C1-C6 alkyl compound. [Mode 72] In Mode 12, R 2 is a C1-C6 alkyl compound. [Mode 73] In Mode 13, R 2 is a C1-C6 alkyl compound. [Mode 74] In Mode 14, R 2 is a C1-C6 alkyl compound. [Mode 75] In Mode 15, R 2A compound which is a C1-C6 alkyl. [Mode 76] In Mode 16, R 2 A compound which is a C1-C6 alkyl. [Mode 77] In Mode 17, R 2 A compound which is a C1-C6 alkyl. [Mode 78] In Mode 18, R 2 A compound which is a C1-C6 alkyl. [Mode 79] In Mode 19, R 2 A compound which is a C1-C6 alkyl. [Mode 80] In Mode 20, R 2 A compound which is a C1-C6 alkyl. [Mode 81] In Mode 21, R 2 A compound which is a C1-C6 alkyl. [Mode 82] In Mode 22, R 2 A compound which is a C1-C6 alkyl. [Mode 83] In Mode 23, R 2 A compound which is a C1-C6 alkyl. [Mode 84] In Mode 24, R 2 A compound which is a C1-C6 alkyl. [Mode 85] In Mode 25, R 2 A compound which is a C1-C6 alkyl. [Mode 86] In Mode 26, R 2 A compound which is a C1-C6 alkyl. [Mode 87] In Mode 27, R 2 A compound which is a C1-C6 alkyl. [Mode 88] In Mode 28, R 2 A compound which is a C1-C6 alkyl. [Mode 89] In Mode 29, R 2 A compound which is a C1-C6 alkyl. [Mode 90] In Mode 30, R 2 A compound which is a C1-C6 alkyl. [Mode 91] In Mode 31, R 2 A compound which is a C1-C6 alkyl. [Mode 92] In Mode 32, R 2 A compound which is a C1-C6 alkyl. [Mode 93] In Mode 4, R 2 A compound which is an ethyl.

[0245] 〔Mode 94〕In Mode 5, R 2 A compound which is an ethyl.

[0246] 〔Mode 95〕In Mode 6, R 2 A compound which is an ethyl.

[0247] 〔Mode 96〕In Mode 7, R 2 A compound which is an ethyl.

[0248] 〔Mode 97〕In Mode 8, R 2 A compound which is an ethyl.

[0249] 〔Mode 98〕In Mode 9, R 2A compound in which R is ethyl.

[0250] 〔Method 99〕In Method 10, R 2 A compound in which R is ethyl.

[0251] 〔Method 100〕In Method 11, R 2 A compound in which R is ethyl.

[0252] 〔Method 101〕In Method 12, R 2 A compound in which R is ethyl.

[0253] 〔Method 102〕In Method 13, R 2 A compound in which R is ethyl.

[0254] 〔Method 103〕In Method 14, R 2 A compound in which R is ethyl.

[0255] 〔Method 104〕In Method 15, R 2 A compound in which R is ethyl.

[0256] 〔Method 105〕In Method 16, R 2 A compound in which R is ethyl.

[0257] 〔Method 106〕In Method 17, R 2 A compound in which R is ethyl.

[0258] 〔Method 107〕In Method 18, R 2 A compound in which R is ethyl.

[0259] 〔Method 108〕In Method 19, R 2 A compound in which R is ethyl.

[0260] 〔Method 109〕In Method 20, R 2 A compound in which R is ethyl.

[0261] 〔Method 110〕In Method 21, R 2 A compound in which R is ethyl.

[0262] 〔Method 111〕In Method 22, R 2 A compound in which R is ethyl.

[0263] 〔Method 112〕In Method 23, R 2 A compound in which R is ethyl.

[0264] 〔Method 113〕In Method 24, R 2 A compound in which R is ethyl.

[0265] 〔Method 114〕In Method 25, R 2 A compound in which R is ethyl.

[0266] In [Mode 115], in Mode 26, R 2 is a compound where R is ethyl.

[0267] In [Mode 116], in Mode 27, R 2 is a compound where R is ethyl.

[0268] In [Mode 117], in Mode 28, R 2 is a compound where R is ethyl.

[0269] In [Mode 118], in Mode 29, R 2 is a compound where R is ethyl.

[0270] In [Mode 119], in Mode 30, R 2 is a compound where R is ethyl.

[0271] In [Mode 120], in Mode 31, R 2 is a compound where R is ethyl.

[0272] In [Mode 121], in Mode 32, R 2 is a compound where R is ethyl.

[0273] In [Mode 122], in Mode 4, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 123], in Mode 5, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 124], in Mode 6, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 125], in Mode 7, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 126], in Mode 8, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 127], in Mode 9, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 128], in Mode 10, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 129], in Mode 11, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 130], in Mode 12, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 131], in Mode 13, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 132], in Mode 14, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 133], in Mode 15, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 134], in Mode 16, W is an oxygen atom, and R 2 is a compound where R is ethyl. In [Mode 135], in Mode 17, W is an oxygen atom, and R 2A compound where R is ethyl. [Scheme 136] In Scheme 18, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 137] In Scheme 19, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 138] In Scheme 20, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 139] In Scheme 21, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 140] In Scheme 22, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 141] In Scheme 23, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 142] In Scheme 24, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 143] In Scheme 25, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 144] In Scheme 26, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 145] In Scheme 27, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 146] In Scheme 28, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 147] In Scheme 29, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 148] In Scheme 30, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 149] In Scheme 31, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 150] In Scheme 32, W is an oxygen atom, R 2 A compound where R is ethyl. [Scheme 151] In Scheme 6, a compound where Q is the group represented by Q1.

[0274] 〔Scheme 152〕In Scheme 7, a compound where Q is the group represented by Q1.

[0275] 〔Scheme 153〕In Scheme 6, a compound where Q is the group represented by Q2.

[0276] 〔Scheme 154〕In Scheme 7, a compound where Q is the group represented by Q2.

[0277] [Mode 155] In Mode 8, a compound in which Het is the group represented by Het1. [Mode 156] In Mode 9, a compound in which Het is the group represented by Het1. [Mode 157] In Mode 10, a compound in which Het is the group represented by Het1. [Mode 158] In Mode 11, a compound in which Het is the group represented by Het1. [Mode 159] In Mode 12, a compound in which Het is the group represented by Het1. [Mode 160] In Mode 13, a compound in which Het is the group represented by Het1. [Mode 161] In Mode 14, a compound in which Het is the group represented by Het1. [Mode 162] In Mode 15, a compound in which Het is the group represented by Het1. [Mode 163] In Mode 16, a compound in which Het is the group represented by Het1. [Mode 164] In Mode 17, a compound in which Het is the group represented by Het1. [Mode 165] In Mode 18, a compound in which Het is the group represented by Het1. [Mode 166] In Mode 19, a compound in which Het is the group represented by Het1. [Mode 167] In Mode 20, a compound in which Het is the group represented by Het1. [Mode 168] In Mode 21, a compound in which Het is the group represented by Het1. [Mode 169] In Mode 22, a compound in which Het is the group represented by Het1. [Mode 170] In Mode 23, a compound in which Het is the group represented by Het1. [Mode 171] In Mode 24, a compound in which Het is the group represented by Het1. [Mode 172] In Mode 25, a compound in which Het is the group represented by Het1. [Mode 173] In Mode 26, a compound in which Het is the group represented by Het1. [Mode 174] In Mode 27, a compound in which Het is the group represented by Het1. [Mode 175] In Mode 28, a compound in which Het is the group represented by Het1. [Mode 176] In Mode 29, a compound in which Het is the group represented by Het1. [Mode 177] In Mode 30, a compound in which Het is the group represented by Het1. [Mode 178] In Mode 31, a compound in which Het is the group represented by Het1. [Mode 179] In Mode 32, a compound in which Het is the group represented by Het1. [Mode 180] In Mode 8, a compound in which Het is the group represented by Het2. [Mode 181] In Mode 9, a compound in which Het is the group represented by Het2. [Mode 182] In Mode 10, a compound in which Het is the group represented by Het2. [Mode 183] In Mode 11, a compound in which Het is the group represented by Het2. [Mode 184] In Mode 12, a compound in which Het is the group represented by Het2. [Mode 185] In Mode 13, a compound in which Het is the group represented by Het2. [Mode 186] In Mode 14, a compound in which Het is the group represented by Het2.[Mode 187] In Mode 15, a compound in which Het is the group represented by Het2. [Mode 188] In Mode 16, a compound in which Het is the group represented by Het2. [Mode 189] In Mode 17, a compound in which Het is the group represented by Het2. [Mode 190] In Mode 18, a compound in which Het is the group represented by Het2. [Mode 191] In Mode 19, a compound in which Het is the group represented by Het2. [Mode 192] In Mode 20, a compound in which Het is the group represented by Het2. [Mode 193] In Mode 21, a compound in which Het is the group represented by Het2. [Mode 194] In Mode 22, a compound in which Het is the group represented by Het2.

[0278] [Mode 195] In Mode 23, a compound in which Het is the group represented by Het2.

[0279] [Mode 196] In Mode 24, a compound in which Het is the group represented by Het2.

[0280] [Mode 197] In Mode 25, a compound in which Het is the group represented by Het2.

[0281] [Mode 198] In Mode 26, a compound in which Het is the group represented by Het2.

[0282] [Mode 199] In Mode 27, a compound in which Het is the group represented by Het2.

[0283] [Mode 200] In Mode 28, a compound in which Het is the group represented by Het2.

[0284] [Mode 201] In Mode 29, a compound in which Het is the group represented by Het2.

[0285] [Mode 202] In Mode 30, a compound in which Het is the group represented by Het2.

[0286] [Mode 203] In Mode 31, a compound in which Het is the group represented by Het2.

[0287] [Mode 204] In Mode 32, a compound in which Het is the group represented by Het2.

[0288] [Mode 205] In any one of Modes 1 to 5, Modes 8 to 154, or Compound N of the present invention, Het is the group represented by Het1, and the combination of B 1 , B 2 and B 3 is: B 1 is CR 6a , B 2 is CR6b and B 3 is a combination of CR 6c ; B 1 is a nitrogen atom, B 2 is a combination of CR 6b and B 3 is a combination of CR 6c ; B 1 is a combination of CR 6a and B 2 is a nitrogen atom, B 3 is a combination of CR 6c ; or, B 1 is a combination of CR 6a and B 2 is a combination of CR 6b and B 3 is a nitrogen atom, and the compound of the combination.

[0289] 〔Mode 206〕Among any one of Modes 1 to 5, Modes 8 to 154, or the compound N of the present invention, Het is the group represented by Het1, and B 1 , B 2 and B 3 The combination is: B 1 is a combination of CR 6a and B 2 is a combination of CR 6b and B 3 is a combination of CR 6c ; B 1 is a nitrogen atom, B 2 is a combination of CR 6b and B 3 is a combination of CR 6c ; B 1 is a combination of CR 6a and B 2 is a nitrogen atom, B 3 is a combination of CR 6c ; or, B 1 is a combination of CR 6a and B 2 is a combination of CR 6b and B 3 is a nitrogen atom, R 6a , R 6b and R 6c are the same or different from each other and are a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, OR 72 or a hydrogen atom, and the compound.

[0290] [Scheme 207] Among any one of Scheme 1 to Scheme 5, Scheme 8 to Scheme 154, or Compound N of the present invention, Het is the group represented by Het1, and B 1 is CR 6a , and B 2 is CR 6b , and B 3 is CR 6c , and R 6a is a hydrogen atom, and R 6b and R 6c are the same or different from each other and are a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 .

[0291] [Scheme 208] Among any one of Scheme 1 to Scheme 5, Scheme 8 to Scheme 154, or Compound N of the present invention, Het is the group represented by Het1, and B 1 is a nitrogen atom, and B 2 is CR 6b , and B 3 is CR 6c , and R 6b is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 , and R 6c is a hydrogen atom.

[0292] [Scheme 209] Among any one of Scheme 1 to Scheme 5, Scheme 8 to Scheme 154, or Compound N of the present invention, Het is the group represented by Het1, and B 1 is a nitrogen atom, and B 2 is CR 6b , and B 3 is CR 6c , and R 6b is a hydrogen atom, and R 6c is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 .

[0293] [Scheme 210] Among any one of Scheme 1 to Scheme 5, Scheme 8 to Scheme 154, or Compound N of the present invention, Het is the group represented by Het1, and B 1 is CR 6a , and B 2 is a nitrogen atom, and B 3 is CR 6c , and R6a and R 6c are the same as or different from each other and are a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 compound.

[0294] 〔Mode 211〕Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is a group represented by Het1, and B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 compound.

[0295] 〔Mode 212〕Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is a group represented by Het1, and B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 , R 6b is a hydrogen atom compound.

[0296] 〔Mode 213〕Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is a group represented by Het2, and B 1 , B 2 and B 3 combination is: B 1 is CR 6a , B 2 is CR 6b , B 3 is CR 6c combination; B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c combination; B 1 is CR6a and B 2 is a nitrogen atom, and B 3 is CR 6c ; or B 1 is CR 6a and B 2 is CR 6b and B 3 is a nitrogen atom, and R 6a , R 6b and R 6c are the same as or different from each other and are a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, OR 72 or a hydrogen atom.

[0297] 〔Mode 214〕In any one of Modes 1 to 5, Modes 8 to 154, or the compound N of the present invention, Het is a group represented by Het2, and B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, and R 6b is a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 .

[0298] 〔Mode 215〕In any one of Modes 1 to 5, Modes 8 to 154, or the compound N of the present invention, Het is a group represented by Het1, and the combination of A 2 and A 3 is: A 2 is -CR 7a R 7b -, and A 3 is -CR 7c R 7d -; the combination of A 2 is -CR 7a R 7b -, and A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position to A 2 ); the combination of A 2 is -NR 5a -, and A 3-CR 7c R 7d - combination; or, A 2 is -NR 5a -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position with A 2 ) combination of compounds.

[0299] [Mode 216] Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is the group shown by Het1, and the combination of A 2 and A 3 is: A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d - combination; or, A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position with A 2 ) combination of compounds.

[0300] [Mode 217] Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is the group shown by Het2, and the combination of A 2 and A 4 is: A 2 is -CR 7a R 7b -, A 4 is -CR 7o R 7p - combination; A 2 is -CR 7a R 7b -, A 4 is -CR 7q R 7r -CR 7s R 7t -* 2 (* 2 represents the bonding position with A 2 ) combination; A2 is -CR 7a R 7b -, A 4 is -NR 5c -CR 7u R 7v -* 2 (* 2 represents the combination with A 2 (bonding position)); A 2 is -NR 5a -, A 4 is -CR 7o R 7p -; or, A 2 is -NR 5a -, A 4 is -CR 7q R 7r -CR 7s R 7t -* 2 (* 2 represents the combination with A 2 (bonding position)) of the compound.

[0301] [Mode 218] Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is the group shown by Het2, and the combination of A 2 and A 4 is: A 2 is -CR 7a R 7b -, A 4 is -CR 7o R 7p -; or, A 2 is -CR 7a R 7b -, A 4 is -CR 7q R 7r -CR 7s R 7t -* 2 (* 2 represents the combination with A 2 (bonding position)) of the compound.

[0302] [Mode 219] Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is the group shown by Het1, and the combination of A 2 and A 3 is: A 2 is -CR 7a R 7b -, A 3 is -CR7c R 7d - combination; or, A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position with A 2 ) combination, R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g and R 7h compounds that are the same as or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0303] 〔Mode 220〕In any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is the group represented by Het1, and A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a and R 7b , and R 7c and R 7d each may together with the carbon atom to which they are bonded form a C3-C4 cycloalkyl group; or, Het is the group represented by Het1, and A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position with A 2 )), R 7a and R 7b , R 7e and R 7f , and R 7g and R 7h compounds that each may together with the carbon atom to which they are bonded form a C3-C4 cycloalkyl group.

[0304] [Scheme 221] In any one of Scheme 1 to Scheme 5, Scheme 8 to Scheme 154, or Compound N of the present invention, Het is the group represented by Het2, A 2 and A 4 The combination is: A 2 is -CR 7a R 7b -, A 4 is -CR 7o R 7p -; or, A 2 is -CR 7a R 7b -, A 4 is -CR 7q R 7r -CR 7s R 7t -* 2 (* 2 represents the bonding position to A 2 ), R 7a , R 7b , R 7o , R 7p , R 7q , R 7r , R 7s and R 7t are the same as or different from each other and are compounds of C1-C6 alkyl or hydrogen atom.

[0305] [Scheme 222] In any one of Scheme 1 to Scheme 5, Scheme 8 to Scheme 154, or Compound N of the present invention, Het is the group represented by Het2, A 2 is -CR 7a R 7b (-), A 4 is -CR 7o R 7p (-), R 7a and R 7b , and R 7o and R 7p each may together with the carbon atom to which they are bonded form C3-C4 cycloalkyl; or, Het is the group represented by Het2, A 2 is -CR 7a R 7b (-), A 4 is -CR 7q R 7r -CR 7s R 7t (-), * 2 (* 2 represents the bonding position to A 2 ), R 7a and R 7b , R7q and R 7r , and R 7s and R 7t Each may, together with the carbon atom to which it is bonded, form a C3-C4 cycloalkyl group.

[0306] 〔Mode 223〕Among any one of Modes 1 to 5, Modes 8 to 154, or the compound N of the present invention, Het is the group represented by Het1, and B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or OR 72 , R 72 is a compound of a C1-C6 chain hydrocarbon group which may be substituted with a halogen atom.

[0307] 〔Mode 224〕Among any one of Modes 1 to 5, Modes 8 to 154, or the compound N of the present invention, Het is the group represented by Het2, and B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or OR 72 , R 72 is a compound of a C1-C6 chain hydrocarbon group which may be substituted with a halogen atom.

[0308] 〔Mode 225〕Among any one of Modes 1 to 5, Modes 8 to 154, or the compound N of the present invention, Het is the group represented by Het1, and B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a halogen atom, or OR 72 , R 72 is a compound of a C1-C6 chain hydrocarbon group which may be substituted with a halogen atom.

[0309] 〔Mode 226〕Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is the group represented by Het2, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a halogen atom, or OR 72 , R 72 is a compound of a C1-C6 chain hydrocarbon group which may be substituted by a halogen atom.

[0310] 〔Mode 227〕Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is the group represented by Het1, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R 7b , R 7c and R 7d are hydrogen atoms.

[0311] 〔Mode 228〕Among any one of Mode 1 to Mode 5, Mode 8 to Mode 154, or Compound N of the present invention, Het is the group represented by Het1, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or OR 72 , R 72 is a C1-C6 chain hydrocarbon group which may be substituted by a halogen atom, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R 7b , R 7c and R 7d are hydrogen atoms.

[0312] 〔Embodiment 229〕In any one of Embodiments 1 to 5, Embodiments 8 to 154, or the compound N of the present invention, Het is the group represented by Het1, and B 1 is CR 6a , and B 2 is CR 6b , and B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, OR 72 or a halogen atom, R 72 is a C1-C6 alkyl group which may be substituted by a halogen atom, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R 7b , R 7c and R 7d are hydrogen atoms.

[0313] As an embodiment of Intermediate A, the following compounds can be cited.

[0314] 〔Embodiment A1〕In Intermediate A, a compound in which W is an oxygen atom.

[0315] 〔Embodiment A2〕In Intermediate A, a compound in which R 2 is a C1-C6 alkyl group.

[0316] 〔Embodiment A3〕In Intermediate A, a compound in which R 2 is an ethyl group.

[0317] 〔Embodiment A4〕In Intermediate A, a compound in which X 1 is a chlorine atom, a bromine atom or an iodine atom.

[0318] 〔Embodiment A5〕In Intermediate A, a compound in which X 1 is a hydroxyl group.

[0319] 〔Embodiment A6〕In Intermediate A, the combination of G 1 , G 2 , G 3 and G 4 is: G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom; G 1 is CR 3a , G2 is CR 3b and G 3 is a nitrogen atom, G 4 is CR 3d 's combination; G 1 is CR 3a and G 2 is a nitrogen atom, G 3 is CR 3c and G 4 is CR 3d 's combination; G 1 is a nitrogen atom, G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d 's combination; or G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d 's combination, R 3a and R 3c and R 3d is a hydrogen atom, R 3b is a C1-C6 alkyl group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a phenyl group that can be substituted by one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more halogen atoms, or a halogen atom compound.

[0320] 〔Mode A7〕In intermediate A, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a and R 3c and R 3d is a hydrogen atom, R 3b is a C1-C6 alkyl group that can be substituted by one or more halogen atoms, or a halogen atom compound.

[0321] 〔Mode A8〕In intermediate A, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR3c , G 4 is CR 3d , R 3a , R 3c and R 3d are hydrogen atoms, and R 3b is a C1-C6 alkyl group that can be substituted by one or more halogen atoms, or a halogen atom compound.

[0322] 〔Mode A9〕In intermediate A, the combination of G 1 , G 2 , G 3 and G 4 is: G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom; G 1 is CR 3a , G 2 is CR 3b , G 3 is a nitrogen atom, G 4 is CR 3d , G 1 is CR 3a , G 2 is a nitrogen atom, G 3 is CR 3c , G 4 is CR 3d , G 1 is a nitrogen atom, G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d , or G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d , G 3a , R 3b and R 3d are hydrogen atoms, and R 3c is a halogen atom compound.

[0323] 〔Mode A10〕In intermediate A, G 1 is CR 3a , G 2 is CR 3b, G 3 is CR 3c , G 4 is a nitrogen atom or CR 3d , R 3a , R 3b and R 3d are hydrogen atoms, and a compound in which R 3c is a halogen atom.

[0324] 〔Mode A11〕In intermediate A, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d , R 3a , R 3b and R 3d are hydrogen atoms, and a compound in which R 3c is a halogen atom.

[0325] 〔Mode A12〕In intermediate A, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d , R 3a , R 3c and R 3d are hydrogen atoms, and a compound in which R 3b is a halogen atom.

[0326] 〔Mode A13〕In Mode A2, a compound in which W is an oxygen atom.

[0327] 〔Mode A14〕In Mode A3, a compound in which W is an oxygen atom.

[0328] 〔Mode A15〕In Mode A4, a compound in which W is an oxygen atom.

[0329] 〔Mode A16〕In Mode A5, a compound in which W is an oxygen atom.

[0330] 〔Mode A17〕In Mode A6, a compound in which W is an oxygen atom.

[0331] 〔Mode A18〕In Mode A7, a compound in which W is an oxygen atom.

[0332] 〔Mode A19〕In Mode A8, a compound in which W is an oxygen atom.

[0333] 〔Embodiment A20〕In Embodiment A9, a compound in which W is an oxygen atom.

[0334] 〔Embodiment A21〕In Embodiment A10, a compound in which W is an oxygen atom.

[0335] 〔Embodiment A22〕In Embodiment A11, a compound in which W is an oxygen atom.

[0336] 〔Embodiment A23〕In Embodiment A12, a compound in which W is an oxygen atom.

[0337] 〔Embodiment A24〕In Embodiment A4, a compound in which R 2 is a C1-C6 alkyl group.

[0338] 〔Embodiment A25〕In Embodiment A5, a compound in which R 2 is a C1-C6 alkyl group.

[0339] 〔Embodiment A26〕In Embodiment A6, a compound in which R 2 is a C1-C6 alkyl group.

[0340] 〔Embodiment A27〕In Embodiment A7, a compound in which R 2 is a C1-C6 alkyl group.

[0341] 〔Embodiment A28〕In Embodiment A8, a compound in which R 2 is a C1-C6 alkyl group.

[0342] 〔Embodiment A29〕In Embodiment A9, a compound in which R 2 is a C1-C6 alkyl group.

[0343] 〔Embodiment A30〕In Embodiment A10, a compound in which R 2 is a C1-C6 alkyl group.

[0344] 〔Embodiment A31〕In Embodiment A11, a compound in which R 2 is a C1-C6 alkyl group.

[0345] 〔Embodiment A32〕In Embodiment A12, a compound in which R 2 is a C1-C6 alkyl group.

[0346] 〔Embodiment A33〕In Embodiment A4, a compound in which R 2 is an ethyl group.

[0347] 〔Embodiment A34〕In Embodiment A5, a compound in which R 2 is an ethyl group.

[0348] 〔Embodiment A35〕In Embodiment A6, a compound in which R 2 is an ethyl group.

[0349] 〔Embodiment A36〕In Embodiment A7, a compound in which R2 A compound where R is ethyl.

[0350] 〔Embodiment A37〕In Embodiment A8, R 2 A compound where R is ethyl.

[0351] 〔Embodiment A38〕In Embodiment A9, R 2 A compound where R is ethyl.

[0352] 〔Embodiment A39〕In Embodiment A10, R 2 A compound where R is ethyl.

[0353] 〔Embodiment A40〕In Embodiment A11, R 2 A compound where R is ethyl.

[0354] 〔Embodiment A41〕In Embodiment A12, R 2 A compound where R is ethyl.

[0355] 〔Embodiment A42〕In Embodiment A4, W is an oxygen atom, R 2 A compound where R is ethyl.

[0356] 〔Embodiment A43〕In Embodiment A5, W is an oxygen atom, R 2 A compound where R is ethyl.

[0357] 〔Embodiment A44〕In Embodiment A6, W is an oxygen atom, R 2 A compound where R is ethyl.

[0358] 〔Embodiment A45〕In Embodiment A7, W is an oxygen atom, R 2 A compound where R is ethyl.

[0359] 〔Embodiment A46〕In Embodiment A8, W is an oxygen atom, R 2 A compound where R is ethyl.

[0360] 〔Embodiment A47〕In Embodiment A9, W is an oxygen atom, R 2 A compound where R is ethyl.

[0361] 〔Embodiment A48〕In Embodiment A10, W is an oxygen atom, R 2 A compound where R is ethyl.

[0362] 〔Embodiment A49〕In Embodiment A11, W is an oxygen atom, R 2 A compound where R is ethyl.

[0363] 〔Embodiment A50〕In Embodiment A12, W is an oxygen atom, R 2 A compound where R is ethyl.

[0364] 〔Embodiment A51〕In Embodiment A6, X 1A compound containing a chlorine atom, a bromine atom or an iodine atom.

[0365] [Method A52] In method A7, X 1 A compound containing a chlorine atom, a bromine atom or an iodine atom.

[0366] [Method A53] In method A8, X 1 A compound containing a chlorine atom, a bromine atom or an iodine atom.

[0367] [Method A54] In method A9, X 1 A compound containing a chlorine atom, a bromine atom or an iodine atom.

[0368] [Method A55] In method A10, X 1 A compound containing a chlorine atom, a bromine atom or an iodine atom.

[0369] [Method A56] In method A11, X 1 A compound containing a chlorine atom, a bromine atom or an iodine atom.

[0370] [Method A57] In method A12, X 1 A compound containing a chlorine atom, a bromine atom or an iodine atom.

[0371] [Method A58] In method A6, X 1 A compound containing hydroxyl groups.

[0372] [Method A59] In method A7, X 1 A compound containing hydroxyl groups.

[0373] [Method A60] In method A8, X 1 A compound containing hydroxyl groups.

[0374] [Method A61] In method A9, X 1 A compound containing hydroxyl groups.

[0375] [Method A62] In method A10, X 1 A compound containing hydroxyl groups.

[0376] [Method A63] In method A11, X 1 A compound containing hydroxyl groups.

[0377] [Method A64] In method A12, X 1 A compound containing hydroxyl groups.

[0378] [Form A65] In any one of Form A1 to Form A64 or Intermediate A, B 1 , B 2 and B 3 The combination is: B 1 CR6a , B 2 is CR 6b , B 3 is CR 6c a combination of; B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c a combination of; B 1 is CR 6a , B 2 is a nitrogen atom, B 3 is CR 6c a combination of; or, B 1 is CR 6a , B 2 is CR 6b , B 3 a combination of a nitrogen atom, a compound of

[0379] [Mode A66] In any one of Modes A1 to A64 or Intermediate A, B 1 , B 2 and B 3 a combination of is: B 1 is CR 6a , B 2 is CR 6b , B 3 is CR 6c a combination of; B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c a combination of; B 1 is CR 6a , B 2 is a nitrogen atom, B 3 is CR 6c a combination of; or, B 1 is CR 6a , B 2 is CR 6b , B 3 is a combination of a nitrogen atom, R 6a , R 6b and R 6c are the same or different from each other and are a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, OR 72 or a hydrogen atom, a compound of

[0380] [Mode A67] In any one of Modes A1 to A64 or Intermediate A, B 1 is CR6a , B 2 is CR 6b , B 3 is CR 6c , R 6a is a hydrogen atom, R 6b and R 6c are the same as or different from each other and are a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 compound.

[0381] 〔Mode A68〕In any one of Modes A1 to A64 or Intermediate A, B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c , R 6b is a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 , R 6c is a hydrogen atom compound.

[0382] 〔Mode A69〕In any one of Modes A1 to A64 or Intermediate A, B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c , R 6b is a hydrogen atom, R 6c is a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 compound.

[0383] 〔Mode A70〕In any one of Modes A1 to A64 or Intermediate A, B 1 is CR 6a , B 2 is a nitrogen atom, B 3 is CR 6c , R 6a and R 6c are the same as or different from each other and are a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, or OR 72 compound.

[0384] In any one of [Mode A71], [Mode A1] to [Mode A64] or Intermediate A, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR 72 compound.

[0385] 〔Mode A72〕In any one of [Mode A1] to [Mode A64] or Intermediate A, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR 72 , R 6b is a hydrogen atom compound.

[0386] 〔Mode A73〕In any one of [Mode A1] to [Mode A64] or Intermediate A, the combination of A 2 and A 3 is: A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d - combination; A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position with A 2 ) combination; A 2 is -NR 5a -, A 3 is -CR 7c R 7d - combination; or, A 2 is -NR 5a -, A 3 is -CR 7e R7f -CR 7g R 7h -* 1 (* 1 represents a compound in combination with the bonding position to A 2 ).

[0387] 〔Mode A74〕In any one of Modes A1 to A64 or Intermediate A, the combination of A 2 and A 3 is: A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -; or, A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents a compound in combination with the bonding position to A 2 ).

[0388] 〔Mode A75〕In any one of Modes A1 to A64 or Intermediate A, the combination of A 2 and A 3 is: A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -; or, A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents a compound in combination with the bonding position to A 2 ), where R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g and R 7h are the same or different from each other and are compounds of C1-C6 alkyl or hydrogen atom.

[0389] 〔Mode A76〕In any one of Modes A1 to A64 or Intermediate A, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a and R 7b and, R 7c and R 7d each may together with the carbon atom to which they are bonded form a C3-C4 cycloalkyl group; or, A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position to A 2 ), R 7a and R 7b , R 7e and R 7f and, R 7g and R 7h each may together with the carbon atom to which they are bonded form a C3-C4 cycloalkyl group compound.

[0390] 〔Mode A77〕In any one of Modes A1 to A64 or Intermediate A, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or OR 72 , R 72 is a C1-C6 chain hydrocarbon group which may be substituted by a halogen atom compound.

[0391] 〔Mode A78〕In any one of Modes A1 to A64 or Intermediate A, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R 7b , R 7c and R 7d are hydrogen atom compounds.

[0392] 〔Mode A79〕In any one of Modes A1 to A64 or Intermediate A, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, or OR 72 , R 72 is a C1-C6 chain hydrocarbon group that may be substituted by a halogen atom, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R 7b , R 7c and R 7d are hydrogen atom compounds.

[0393] 〔Mode A80〕In any one of Modes A1 to A64 or Intermediate A, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 alkyl group that may be substituted by one or more halogen atoms, or OR 72 , R 72 is a C1-C6 alkyl group that may be substituted by a halogen atom, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R 7b , R 7c and R 7d are hydrogen atom compounds.

[0394] 〔Mode A81〕In any one of Modes A1 to A64 or Intermediate A, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a halogen atom or OR72 ,R 72 is a compound of a C1-C6 chain hydrocarbon group that can be substituted by a halogen atom.

[0395] As a way of Intermediate B, the following compounds can be cited.

[0396] 〔Mode B1〕In Intermediate B, a compound in which W is an oxygen atom.

[0397] 〔Mode B2〕In Intermediate B, R 2 is a compound of a C1-C6 alkyl group.

[0398] 〔Mode B3〕In Intermediate B, R 2 is a compound of an ethyl group.

[0399] 〔Mode B4〕In Intermediate B, X 2 is a compound of a chlorine atom, a bromine atom or an iodine atom.

[0400] 〔Mode B5〕In Intermediate B, X 2 is a compound of a hydroxyl group.

[0401] 〔Mode B6〕In Intermediate B, G 1 , G 2 , G 3 and G 4 The combination is: G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom; G 1 is CR 3a , G 2 is CR 3b , G 3 is a nitrogen atom, G 4 is CR 3d ; G 1 is CR 3a , G 2 is a nitrogen atom, G 3 is CR 3c , G 4 is CR 3d , G 1 is a nitrogen atom, G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d ; or G 1 is CR 3a is CR2 is CR 3b 、G 3 is CR 3c 、G 4 is CR 3d a combination of, R 3a 、R 3c and R 3d is a hydrogen atom, R 3b is a C1-C6 alkyl group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a phenyl group that can be substituted by one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more halogen atoms, or a compound of a halogen atom.

[0402] 〔Mode B7〕In intermediate B, G 1 is CR 3a ,G 2 is CR 3b ,G 3 is CR 3c ,G 4 is a nitrogen atom or CR 3d ,R 3a 、R 3c and R 3d is a hydrogen atom, R 3b is a C1-C6 alkyl group that can be substituted by one or more halogen atoms, or a compound of a halogen atom.

[0403] 〔Mode B8〕In intermediate B, G 1 is CR 3a ,G 2 is CR 3b ,G 3 is CR 3c ,G 4 is CR 3d ,R 3a 、R 3c and R 3d is a hydrogen atom, R 3b is a C1-C6 alkyl group that can be substituted by one or more halogen atoms, or a compound of a halogen atom.

[0404] 〔Mode B9〕In intermediate B, the combination of G 1 、G 2 、G 3 and G 4 is: G 1 is CR 3a 、G 2 is CR 3b 、G 3 is CR 3c 、G 4is a combination of nitrogen atoms; G 1 is CR 3a 、G 2 is CR 3b 、G 3 is a nitrogen atom, G 4 is CR 3d ; a combination of G 1 is CR 3a 、G 2 is a nitrogen atom, G 3 is CR 3c 、G 4 is CR 3d ; a combination of G 1 is a nitrogen atom, G 2 is CR 3b 、G 3 is CR 3c 、G 4 is CR 3d ; or G 1 is CR 3a 、G 2 is CR 3b 、G 3 is CR 3c 、G 4 is CR 3d ; a combination of R 3a 、R 3b and R 3d are hydrogen atoms, and R 3c is a halogen atom compound.

[0405] 〔Mode B10〕In intermediate B, G 1 is CR 3a ,G 2 is CR 3b ,G 3 is CR 3c ,G 4 is a nitrogen atom or CR 3d ,R 3a 、R 3b and R 3d are hydrogen atoms, and R 3c is a halogen atom compound.

[0406] 〔Mode B11〕In intermediate B, G 1 is CR 3a ,G 2 is CR 3b ,G 3 is CR 3c ,G 4 is CR 3d ,R 3a 、R 3b and R 3dis a hydrogen atom, R 3c is a compound of a halogen atom.

[0407] 〔Mode B12〕In intermediate B, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a 、R 3c and R 3d are hydrogen atoms, and R 3b is a compound of a halogen atom.

[0408] 〔Mode B13〕In Mode B2, a compound where W is an oxygen atom.

[0409] 〔Mode B14〕In Mode B3, a compound where W is an oxygen atom.

[0410] 〔Mode B15〕In Mode B4, a compound where W is an oxygen atom.

[0411] 〔Mode B16〕In Mode B5, a compound where W is an oxygen atom.

[0412] 〔Mode B17〕In Mode B6, a compound where W is an oxygen atom.

[0413] 〔Mode B18〕In Mode B7, a compound where W is an oxygen atom.

[0414] 〔Mode B19〕In Mode B8, a compound where W is an oxygen atom.

[0415] 〔Mode B20〕In Mode B9, a compound where W is an oxygen atom.

[0416] 〔Mode B21〕In Mode B10, a compound where W is an oxygen atom.

[0417] 〔Mode B22〕In Mode B11, a compound where W is an oxygen atom.

[0418] 〔Mode B23〕In Mode B12, a compound where W is an oxygen atom.

[0419] 〔Mode B24〕In Mode B4, a compound where R 2 is a C1-C6 alkyl group.

[0420] 〔Mode B25〕In Mode B5, a compound where R 2 is a C1-C6 alkyl group.

[0421] 〔Mode B26〕In Mode B6, R 2A compound that is a C1-C6 alkyl group.

[0422] 〔Mode B27〕In Mode B7, R 2 A compound that is a C1-C6 alkyl group.

[0423] 〔Mode B28〕In Mode B8, R 2 A compound that is a C1-C6 alkyl group.

[0424] 〔Mode B29〕In Mode B9, R 2 A compound that is a C1-C6 alkyl group.

[0425] 〔Mode B30〕In Mode B10, R 2 A compound that is a C1-C6 alkyl group.

[0426] 〔Mode B31〕In Mode B11, R 2 A compound that is a C1-C6 alkyl group.

[0427] 〔Mode B32〕In Mode B12, R 2 A compound that is a C1-C6 alkyl group.

[0428] 〔Mode B33〕In Mode B4, R 2 A compound that is an ethyl group.

[0429] 〔Mode B34〕In Mode B5, R 2 A compound that is an ethyl group.

[0430] 〔Mode B35〕In Mode B6, R 2 A compound that is an ethyl group.

[0431] 〔Mode B36〕In Mode B7, R 2 A compound that is an ethyl group.

[0432] 〔Mode B37〕In Mode B8, R 2 A compound that is an ethyl group.

[0433] 〔Mode B38〕In Mode B9, R 2 A compound that is an ethyl group.

[0434] 〔Mode B39〕In Mode B10, R 2 A compound that is an ethyl group.

[0435] 〔Mode B40〕In Mode B11, R 2 A compound that is an ethyl group.

[0436] 〔Mode B41〕In Mode B12, R 2 A compound that is an ethyl group.

[0437] 〔Method B42〕In Method B4, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0438] 〔Method B43〕In Method B5, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0439] 〔Method B44〕In Method B6, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0440] 〔Method B45〕In Method B7, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0441] 〔Method B46〕In Method B8, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0442] 〔Method B47〕In Method B9, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0443] 〔Method B48〕In Method B10, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0444] 〔Method B49〕In Method B11, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0445] 〔Method B50〕In Method B12, when W is an oxygen atom and R 2 is a compound with an ethyl group.

[0446] 〔Method B51〕In Method B6, when X 2 is a compound with a chlorine atom, a bromine atom, or an iodine atom.

[0447] 〔Method B52〕In Method B7, when X 2 is a compound with a chlorine atom, a bromine atom, or an iodine atom.

[0448] 〔Method B53〕In Method B8, when X 2 is a compound with a chlorine atom, a bromine atom, or an iodine atom.

[0449] 〔Method B54〕In Method B9, when X 2 is a compound with a chlorine atom, a bromine atom, or an iodine atom.

[0450] 〔Method B55〕In Method B10, when X 2 is a compound with a chlorine atom, a bromine atom, or an iodine atom.

[0451] 〔Method B56〕In Method B11, when X 2A compound in which X is a chlorine atom, a bromine atom or an iodine atom.

[0452] 〔Scheme B57〕In Scheme B12, X 2 A compound in which X is a chlorine atom, a bromine atom or an iodine atom.

[0453] 〔Scheme B58〕In Scheme B6, X 2 A compound in which X is a hydroxyl group.

[0454] 〔Scheme B59〕In Scheme B7, X 2 A compound in which X is a hydroxyl group.

[0455] 〔Scheme B60〕In Scheme B8, X 2 A compound in which X is a hydroxyl group.

[0456] 〔Scheme B61〕In Scheme B9, X 2 A compound in which X is a hydroxyl group.

[0457] 〔Scheme B62〕In Scheme B10, X 2 A compound in which X is a hydroxyl group.

[0458] 〔Scheme B63〕In Scheme B11, X 2 A compound in which X is a hydroxyl group.

[0459] 〔Scheme B64〕In Scheme B12, X 2 A compound in which X is a hydroxyl group.

[0460] 〔Scheme B65〕In any one of Schemes B1 to B64 or Intermediate B, the combination of B 1 , B 2 and B 3 is: B 1 is CR 6a , B 2 is CR 6b , B 3 is CR 6c ; B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c ; or B 1 is CR 6a , B 2 is a nitrogen atom, B 3 is CR 6c ; or B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom.

[0461] In any one of [Mode B66] Mode B1 to Mode B64 or Intermediate B, B 1 , B 2 and B 3 have the following combinations: B 1 is CR 6a , B 2 is CR 6b , B 3 is CR 6c ; B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c ; B 1 is CR 6a , B 2 is a nitrogen atom, B 3 is CR 6c ; or, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, and R 6a , R 6b and R 6c are the same or different from each other and are a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, OR 72 or a hydrogen atom.

[0462] 〔Mode B67〕In any one of Mode B1 to Mode B64 or Intermediate B, B 1 is CR 6a , B 2 is CR 6b , B 3 is CR 6c , R 6a is a hydrogen atom, R 6b and R 6c are the same or different from each other and are a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR 72 .

[0463] 〔Mode B68〕In any one of Mode B1 to Mode B64 or Intermediate B, B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c , R6b is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR 72 , R 6c is a compound of a hydrogen atom.

[0464] 〔Mode B69〕In any one of Modes B1 to B64 or Intermediate B, B 1 is a nitrogen atom, B 2 is CR 6b , B 3 is CR 6c , R 6b is a hydrogen atom, R 6c is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR 72 compound.

[0465] 〔Mode B70〕In any one of Modes B1 to B64 or Intermediate B, B 1 is CR 6a , B 2 is a nitrogen atom, B 3 is CR 6c , R 6a and R 6c are the same or different from each other and are a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR 72 compound.

[0466] 〔Mode B71〕In any one of Modes B1 to B64 or Intermediate B, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR 72 compound.

[0467] 〔Mode B72〕In any one of Modes B1 to B64 or Intermediate B, B 1 is CR 6a , B 2 is CR 6b , B 3is a nitrogen atom, R 6a is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR 72 is a hydrogen atom. 6b Compound.

[0468] 〔Mode B73〕In any one of Modes B1 to B64 or Intermediate B, A 2 and A 3 The combination is: A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d - combination; A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position with A 2 ) combination; A 2 is -NR 5a -, A 3 is -CR 7c R 7d - combination; or, A 2 is -NR 5a -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position with A 2 ) combination of compounds.

[0469] 〔Mode B74〕In any one of Modes B1 to B64 or Intermediate B, A 2 and A 3 The combination is: A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d - combination; or, A 2 is -CR 7a R 7b -, A 3 is -CR7e R 7f -CR 7g R 7h -* 1 (* 1 represents a compound in combination with the bonding position to A 2 ).

[0470] 〔Mode B75〕In any one of Modes B1 to B64 or Intermediate B, the combination of A 2 and A 3 is: A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -; or, A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -* 1 (* 1 represents the bonding position to A 2 ), and the compounds of R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g and R 7h are the same as or different from each other and are C1-C6 alkyl groups or hydrogen atoms.

[0471] 〔Mode B76〕In any one of Modes B1 to B64 or Intermediate B, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a and R 7b , and also R 7c and R 7d each may together with the carbon atom to which they are bonded form a C3-C4 cycloalkyl group; or, A 2 is -CR 7a R 7b -, A 3 is -CR 7e R 7f -CR 7g R 7h -*1 (* 1 represents the bonding position with A 2 , R 7a and R 7b , R 7e and R 7f , and R 7g and R 7h each can form a C3-C4 cycloalkyl compound together with the carbon atom to which they are bonded.

[0472] 〔Mode B77〕In any one of Modes B1 to B64 or Intermediate B, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or OR 72 , R 72 is a C1-C6 chain hydrocarbon group that can be substituted by a halogen atom.

[0473] 〔Mode B78〕In any one of Modes B1 to B64 or Intermediate B, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R 7b , R 7c and R 7d are hydrogen atoms.

[0474] 〔Mode B79〕In any one of Modes B1 to B64 or Intermediate B, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or OR 72 , R 72 is a C1-C6 chain hydrocarbon group that can be substituted by a halogen atom, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R7b , R 7c and R 7d is a compound of a hydrogen atom.

[0475] [Mode B80] Among any one of Modes B1 to B64 or Intermediate B, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 alkyl group which may be substituted by one or more halogen atoms, or OR 72 , R 72 is a C1-C6 alkyl group which may be substituted by a halogen atom, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d -, R 7a , R 7b , R 7c and R 7d is a compound of a hydrogen atom.

[0476] [Mode B81] Among any one of Modes B1 to B64 or Intermediate B, B 1 is CR 6a , B 2 is CR 6b , B 3 is a nitrogen atom, R 6a is a hydrogen atom, R 6b is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a halogen atom or OR 72 , R 72 is a compound of a C1-C6 chain hydrocarbon group which may be substituted by a halogen atom.

[0477] Next, a method for manufacturing the compound of the present invention will be described.

[0478] Manufacturing Method 1

[0479] The compound represented by the formula (I-b) (hereinafter referred to as compound (I-b)) or the compound represented by the formula (I-c) (hereinafter referred to as compound (I-c)) can be manufactured by reacting the compound represented by the formula (I-a) (hereinafter referred to as compound (I-a)) with an oxidizing agent.

[0480] [Chemical Formula 9]

[0481]

[0482] [In the formula, the symbols represent the same meanings as described above.]

[0483] First, a method for producing compound (I-b) from compound (I-a) is described.

[0484] The reaction is usually carried out in a solvent. Examples of the solvent include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); acetic acid; water; and mixtures of two or more of them.

[0485] Examples of the oxidizing agent include sodium periodate, meta-chloroperoxybenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide.

[0486] When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst can be used as needed.

[0487] Examples of the base include sodium carbonate. When a base is used in the reaction, the base is usually used in a proportion of 0.01 to 1 mole relative to 1 mole of compound (I-a).

[0488] Examples of the catalyst include tungstic acid and sodium tungstate. When a catalyst is used in the reaction, the catalyst is usually used in a proportion of 0.01 to 0.5 mole relative to 1 mole of compound (I-a).

[0489] In the reaction, the oxidizing agent is usually used in a proportion of 1 to 1.2 moles relative to 1 mole of compound (I-a).

[0490] The reaction temperature is usually in the range of -20°C to 80°C. The reaction time is usually in the range of 0.1 to 12 hours.

[0491] After the reaction is completed, water is added to the reaction mixture, and extraction is carried out using an organic solvent. If necessary, the organic layer is washed with an aqueous solution of a reducing agent (such as sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (such as sodium bicarbonate). The organic layer is dried and concentrated, whereby compound (I-b) can be obtained.

[0492] Next, a method for producing compound (I-c) from compound (I-b) is described.

[0493] The reaction is usually carried out in a solvent. Examples of the solvent include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of them.

[0494] Examples of the oxidizing agent include mCPBA and hydrogen peroxide.

[0495] When hydrogen peroxide is used as the oxidizing agent, a base or a catalyst can be used as needed.

[0496] As the base, sodium carbonate can be mentioned, for example. When a base is used in the reaction, the base is usually used in a proportion of 0.01 to 1 mole relative to 1 mole of the compound (I-b).

[0497] As the catalyst, sodium tungstate can be mentioned, for example. When a catalyst is used in the reaction, the catalyst is usually used in a proportion of 0.01 to 0.5 mole relative to 1 mole of the compound (I-b).

[0498] In the reaction, the oxidizing agent is usually used in a proportion of 1 to 2 moles relative to 1 mole of the compound (I-b).

[0499] The reaction temperature is usually in the range of -20°C to 120°C. The reaction time is usually in the range of 0.1 to 12 hours.

[0500] After the reaction is completed, water is added to the reaction mixture, extraction is carried out using an organic solvent, and if necessary, the organic layer is washed with an aqueous solution of a reducing agent (such as sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (such as sodium bicarbonate). The organic layer is dried and concentrated, whereby the compound (I-c) can be obtained.

[0501] In addition, the compound (I-c) can also be produced by a one-step reaction (one-pot) by reacting the compound (I-a) with an oxidizing agent.

[0502] The reaction can be carried out according to the following method: The oxidizing agent is used in a proportion of usually 2 to 5 moles relative to 1 mole of the compound (I-a) to produce the compound (I-c) from the compound (I-b).

[0503] Production Method 2

[0504] The compound represented by the formula (I-S-1) (hereinafter referred to as the compound (I-S-1)) can be produced by reacting the compound represented by the formula (I-O-1) (hereinafter referred to as the compound (I-O-1)) with a sulfurizing agent.

[0505] [Chemical formula 10]

[0506]

[0507] [In the formula, the symbols represent the same meanings as described above.]

[0508] The reaction can be carried out in a solvent or without a solvent. Examples of the solvent include ethers (hereinafter referred to as ethers) such as tetrahydrofuran (hereinafter referred to as THF), methyl tert-butyl ether (hereinafter referred to as MTBE), ethylene glycol dimethyl ether, 1,4-dioxane, cyclopentyl methyl ether, etc.; halogenated hydrocarbons; aromatic hydrocarbons such as toluene and xylene (hereinafter referred to as aromatic hydrocarbons); nitriles; nitrogen-containing aromatic compounds such as pyridine, methylpyridine, dimethylpyridine, quinoline (hereinafter referred to as nitrogen-containing aromatic compounds); and mixtures of two or more of them.

[0509] Examples of the sulfurizing agent include phosphorus pentasulfide, Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide), etc.

[0510] In the reaction, relative to 1 mole of the compound (I-O-1), the sulfurizing agent is usually used in a ratio of 1 mole to 3 moles.

[0511] The reaction temperature is usually in the range of 0 °C to 200 °C. The reaction time is usually in the range of 1 to 24 hours.

[0512] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-S-1).

[0513] Manufacturing Method 3

[0514] The compound represented by the formula (I-S-2) (hereinafter referred to as the compound (I-S-2)) can be produced by reacting the compound represented by the formula (I-O-2) (hereinafter referred to as the compound (I-O-2)) with a sulfurizing agent.

[0515] [Chemical Formula 11]

[0516]

[0517] [In the formula, the symbols have the same meanings as described above.]

[0518] For the compound (I-S-2), the compound (I-O-2) can be used instead of the compound (I-O-1), and it can be produced according to Manufacturing Method 2.

[0519] Manufacturing Method 4

[0520] The compound (I-O-1) can be produced by reacting the compound represented by the formula (M-1) (hereinafter referred to as the compound (M-1)) with the compound represented by the formula (M-2) (hereinafter referred to as the compound (M-2)) in the presence of a base.

[0521] [Chemical Formula 12]

[0522]

[0523] [In the formula, X a represents a leaving group such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc., and other symbols represent the same meanings as described above.]

[0524] The reaction is usually carried out in a solvent. Examples of the solvent include ethers; aromatic hydrocarbons; nitriles; aprotic polar solvents such as N,N-dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), dimethyl sulfoxide (hereinafter referred to as DMSO) (hereinafter referred to as aprotic polar solvent group); and mixtures of two or more of them.

[0525] Examples of the base include organic bases such as triethylamine, N,N-diisopropylethylamine, pyridine, 4-(dimethylamino)pyridine (hereinafter referred to as organic base group); alkali metal carbonates such as sodium carbonate, potassium carbonate, cesium carbonate (hereinafter referred to as alkali metal carbonate group); and alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydride group).

[0526] The reaction can also be carried out using a metal catalyst as needed. Examples of the metal catalyst include copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) trifluoromethanesulfonate benzene complex, tetra(acetonitrile)copper(I) hexafluorophosphate, copper(I) 2-thiophenecarboxylate; nickel catalysts such as bis(cyclooctadiene)nickel(0), nickel(II) chloride; palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0). When a metal catalyst is used in the reaction, the metal catalyst is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (M-1).

[0527] The reaction can also be carried out using a ligand as needed. Examples of the ligand include triphenylphosphine, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (hereinafter referred to as Xantphos), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'-dimethylethylenediamine, etc. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (M-1).

[0528] In the reaction, relative to 1 mole of the compound (M-1), the compound (M-2) is usually used in a ratio of 0.8 to 1.2 moles, and the base is usually used in a ratio of 1 to 3 moles.

[0529] The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.5 to 24 hours.

[0530] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-O-1).

[0531] The compound (M-1) is a commercially available compound or can be manufactured according to the method described in, for example, International Publication No. 2013 / 192346.

[0532] Production method 5

[0533] The compound (I-O-2) can be produced by reacting the compound represented by the formula (M-3) (hereinafter referred to as the compound (M-3)) with the compound (M-2) in the presence of a base.

[0534] [Chemical formula 13]

[0535]

[0536] [In the formula, the symbols represent the same meanings as described above.]

[0537] The reaction can be carried out using the compound (M-3) instead of the compound (M-1) according to Production method 4.

[0538] The compound (M-3) is a commercially available compound or can be produced using a known method.

[0539] Production method 6

[0540] The compound represented by the formula (I-n0-1) (hereinafter referred to as the compound (I-n0-1)) can be produced according to the following synthetic route.

[0541] [Chemical formula 14]

[0542]

[0543] [In the formula, X d represents a chlorine atom, a bromine atom or an iodine atom, and the other symbols represent the same meanings as described above.]

[0544] First, the production method of the compound represented by the formula (M-5) (hereinafter referred to as the compound (M-5)) is described.

[0545] Regarding compound (M-5), the compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) can be used instead of compound (M-2) and produced according to Production Method 4.

[0546] Next, the production method of the compound represented by formula (M-6) (hereinafter referred to as compound (M-6)) will be described.

[0547] Compound (M-6) can be produced by reacting compound (M-5) with a halogenating agent.

[0548] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of them.

[0549] Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, etc.

[0550] In the reaction, relative to 1 mole of compound (M-5), the halogenating agent is usually used in a ratio of 1 to 20 moles.

[0551] The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours.

[0552] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out with an organic solvent. After-treatment operations such as drying and concentrating the organic layer are carried out to obtain compound (M-6).

[0553] Next, the method for producing compound (I-n0-1) from compound (M-5) will be described.

[0554] Compound (I-n0-1) can be produced by reacting compound (M-5), the compound represented by formula (R-1) (hereinafter referred to as compound (R-1)), and a halogenating agent.

[0555] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of them.

[0556] Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, etc.

[0557] In the reaction, relative to 1 mole of compound (M-5), compound (R-1) is usually used in a ratio of 1 to 20 moles, and the halogenating agent is usually used in a ratio of 1 to 20 moles.

[0558] The reaction temperature is generally in the range of -20°C to 200°C. The reaction time is generally in the range of 0.1 to 72 hours.

[0559] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-n0-1).

[0560] Compound (R-1) is a commercially available compound or can be prepared using known methods.

[0561] Next, a method for preparing compound (I-n0-1) from compound (M-6) is described.

[0562] Compound (I-n0-1) can also be prepared by reacting compound (M-6) with compound (R-1) in the presence of a metal catalyst and a base.

[0563] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of them.

[0564] Examples of the metal catalyst include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tris(dibenzylideneacetone)dipalladium(0), palladium(II) acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0), nickel(II) chloride; copper catalysts such as copper(I) iodide, copper(I) chloride; and so on.

[0565] Examples of the base include alkali metal hydrides, alkali metal carbonates, and organic bases.

[0566] In the reaction, a ligand can also be used. Examples of the ligand include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, and so on. When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (M-6).

[0567] In the reaction, compound (R-1) is usually used in a ratio of 1 to 20 moles, the metal catalyst is usually used in a ratio of 0.01 to 0.5 mole, and the base is usually used in a ratio of 0.1 to 5 moles relative to 1 mole of compound (M-6).

[0568] The reaction temperature is generally in the range of -20°C to 200°C. The reaction time is generally in the range of 0.1 to 72 hours.

[0569] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then performed to obtain compound (I-n0-1).

[0570] Manufacturing method 7

[0571] The compound represented by formula (I-n0-2) (hereinafter referred to as compound (I-n0-2)) can be manufactured according to the following synthetic route.

[0572] [Chemical formula 15]

[0573]

[0574] [In the formula, the symbols represent the same meanings as described above.]

[0575] For the compound represented by formula (M-7) (hereinafter referred to as compound (M-7)), compound (M-3) can be used instead of compound (M-1) and manufactured according to manufacturing method 6.

[0576] For the compound represented by formula (M-8) (hereinafter referred to as compound (M-8)), compound (M-7) can be used instead of compound (M-5) and manufactured according to the method of manufacturing compound (M-6) from compound (M-5) in manufacturing method 6.

[0577] For compound (I-n0-2), compound (M-7) can be used instead of compound (M-5) and manufactured according to the method of manufacturing compound (I-n0-1) from compound (M-5) in manufacturing method 6.

[0578] In addition, for compound (I-n0-2), compound (M-8) can also be used instead of compound (M-6) and manufactured according to the method of manufacturing compound (I-n0-1) from compound (M-6) in manufacturing method 6.

[0579] Manufacturing method 8

[0580] Compound (I-O-1) can also be manufactured by reacting the compound represented by formula (M-9-X) (hereinafter referred to as compound (M-9-X)) with a base.

[0581] [Chemical formula 16]

[0582]

[0583] [In the formula, X Arepresents a chlorine atom, a bromine atom or an iodine atom, and other symbols represent the same meanings as described above.

[0584] The reaction is usually carried out in a solvent. Examples of the solvent include ethers; aromatic hydrocarbons; nitriles; aprotic polar solvents; and mixtures of two or more of them.

[0585] Examples of the base include organic bases; alkali metal carbonates; and alkali metal hydrides.

[0586] The reaction can also be carried out using a metal catalyst as needed. Examples of the metal catalyst include copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile)copper(I) hexafluorophosphate, copper(I) 2-thiophenecarboxylate; nickel catalysts such as bis(cyclooctadiene)nickel(0), nickel(II) chloride; palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0). When a metal catalyst is used in the reaction, the metal catalyst is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (M-9-X).

[0587] The reaction can also be carried out using a ligand as needed. Examples of the ligand include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'-dimethylethylenediamine, etc. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (M-9-X).

[0588] In the reaction, the base is usually used in a proportion of 1 to 5 mol relative to 1 mol of the compound (M-9-X).

[0589] The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.5 to 24 hours.

[0590] After the reaction is completed, water can be added to the reaction mixture, and extraction is carried out using an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-O-1).

[0591] Production Method 9

[0592] Compound (I-O-1) can also be produced by subjecting the compound represented by formula (M-9-OH) (hereinafter referred to as compound (M-9-OH)) to intramolecular condensation in the presence of a condensing agent.

[0593] [Chemical formula 17]

[0594]

[0595] [In the formula, the symbols represent the same meanings as described above.]

[0596] The reaction is usually carried out in a solvent. Examples of the solvent include ethers; halogenated hydrocarbons; aromatic hydrocarbons; esters such as ethyl acetate and butyl acetate (hereinafter referred to as esters); nitriles; aprotic polar solvents; nitrogen-containing aromatic compounds; and mixtures of two or more of them.

[0597] Examples of the condensing agent used in the reaction include a mixture of triphenylphosphine and an azodicarboxylate compound. Examples of the azodicarboxylate compound include diethyl azodicarboxylate.

[0598] In the reaction, the condensing agent is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (M-9-OH).

[0599] The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 24 hours.

[0600] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-O-1).

[0601] Production method 10

[0602] Compound (I-O-1) (hereinafter referred to as ) can also be produced by reacting the compound represented by formula (M-10-X) (hereinafter referred to as compound (M-10-X)) with a base.

[0603] [Chemical formula 18]

[0604]

[0605] [In the formula, the symbols represent the same meanings as described above.]

[0606] For compound (I-O-1), compound (M-10-X) can be used instead of compound (M-9-X), and it can be produced according to production method 8.

[0607] Production method 11

[0608] Compound (I-O-1) can also be produced by subjecting the compound represented by formula (M-10-OH) (hereinafter referred to as compound (M-10-OH)) to intramolecular condensation in the presence of a condensing agent.

[0609] [Chemical formula 19]

[0610]

[0611] [In the formula, the symbols represent the same meanings as described above.]

[0612] For compound (I-O-1), compound (M-10-OH) can also be used in place of compound (M-9-OH) and produced according to Production Method 9.

[0613] Production Method 12

[0614] The compound represented by formula (I-b-p) (hereinafter referred to as compound (I-b-p)) or the compound represented by formula (I-c-p) (hereinafter referred to as compound (I-c-p)) can be produced by reacting the compound represented by formula (I-a-p) (hereinafter referred to as compound (I-a-p)) with an oxidizing agent.

[0615] [Chemical formula 20]

[0616]

[0617] [In the formula, the symbols represent the same meanings as described above.]

[0618] For compound (I-b-p), compound (I-a-p) can be used in place of compound (I-a) and produced according to Production Method 1.

[0619] For compound (I-c-p), compound (I-b-p) can be used in place of compound (I-b) and produced according to Production Method 1.

[0620] In addition, for compound (I-c-p), compound (I-a-p) can also be used in place of compound (I-a) and produced according to Production Method 1.

[0621] Production Method 13

[0622] The compound represented by formula (I-S-1p) (hereinafter referred to as compound (I-S-1p)) can be produced by reacting the compound represented by formula (I-O-1p) (hereinafter referred to as compound (I-O-1p)) with a sulfurizing agent.

[0623] [Chemical formula 21]

[0624]

[0625] [In the formula, the symbols represent the same meanings as described above.]

[0626] Regarding the compound (I-S-1p), the compound (I-O-1p) can be used instead of the compound (I-O-1) and manufactured according to Production Method 2.

[0627] Production Method 14

[0628] The compound represented by the formula (I-S-2p) (hereinafter referred to as the compound (I-S-2p)) can be manufactured by reacting the compound represented by the formula (I-O-2p) (hereinafter referred to as the compound (I-O-2p)) with a sulfurizing agent.

[0629] [Chemical Formula 22]

[0630]

[0631] [In the formula, the symbols represent the same meanings as described above.]

[0632] Regarding the compound (I-S-2p), the compound (I-O-2p) can be used instead of the compound (I-O-1) and manufactured according to Production Method 2.

[0633] Production Method 15

[0634] The compound (I-O-1p) can be manufactured by reacting the compound (M-1) with the compound represented by the formula (M-11) (hereinafter referred to as the compound (M-11)) in the presence of a base.

[0635] [Chemical Formula 23]

[0636]

[0637] [In the formula, the symbols represent the same meanings as described above.]

[0638] Regarding the compound (I-O-1p), the compound (M-11) can be used instead of the compound (M-2) and manufactured according to Production Method 4.

[0639] Production Method 16

[0640] The compound (I-O-2p) can be manufactured by reacting the compound (M-3) with the compound (M-11) in the presence of a base.

[0641] [Chemical Formula 24]

[0642]

[0643] [In the formula, the symbols represent the same meanings as described above.]

[0644] Regarding the compound (I-O-2p), the compound (M-11) can be used instead of the compound (M-2) and manufactured according to Production Method 5.

[0645] Production Method 17

[0646] The compound represented by the formula (I-n0-1p) (hereinafter referred to as compound (I-n0-1p)) can be manufactured according to the following synthesis route.

[0647] [Chemical formula 25]

[0648]

[0649] [In the formula, the symbols represent the same meanings as described above.]

[0650] Regarding the compound represented by the formula (M-13) (hereinafter referred to as compound (M-13)), the compound (M-12) can be used instead of the compound (M-4) and manufactured according to Production Method 6.

[0651] The compound (M-12) is a commercially available compound or can be manufactured using known methods.

[0652] Regarding the compound represented by the formula (M-14) (hereinafter referred to as compound (M-14)), the compound (M-13) can be used instead of the compound (M-5) and manufactured according to the method of manufacturing the compound (M-6) from the compound (M-5) in Production Method 6.

[0653] Regarding the compound (I-n0-1p), the compound (M-13) can also be used instead of the compound (M-5) and manufactured according to the method of manufacturing the compound (I-n0-1) from the compound (M-5) in Production Method 6.

[0654] In addition, regarding the compound (I-n0-1p), the compound (M-14) can also be used instead of the compound (M-6) and manufactured according to the method of manufacturing the compound (I-n0-1) from the compound (M-6) in Production Method 6.

[0655] Production Method 18

[0656] The compound represented by the formula (I-n0-2p) (hereinafter referred to as compound (I-n0-2p)) can be manufactured according to the following synthesis route.

[0657] [Chemical formula 26]

[0658]

[0659] [In the formula, the symbols represent the same meanings as described above.]

[0660] For the compound represented by formula (M-15) (hereinafter referred to as compound (M-15)), compound (M-12) can be used instead of compound (M-4) and it can be produced according to Production Method 7.

[0661] For the compound represented by formula (M-16) (hereinafter referred to as compound (M-16)), compound (M-15) can be used instead of compound (M-7) and it can be produced according to the method for producing compound (M-8) from compound (M-7) in Production Method 7.

[0662] For compound (I-n0-2p), compound (M-15) can also be used instead of compound (M-7) and it can be produced according to the method for producing compound (I-n0-2) from compound (M-7) in Production Method 7.

[0663] In addition, for compound (I-n0-2p), compound (M-16) can also be used instead of compound (M-8) and it can be produced according to the method for producing compound (I-n0-2) from compound (M-8) in Production Method 7.

[0664] Production Method 19

[0665] Compound (I-O-1p) can also be produced by reacting the compound represented by formula (M-17-X) (hereinafter referred to as compound (M-17-X)) with a base.

[0666] [Chemical formula 27]

[0667]

[0668] [In the formula, the symbols represent the same meanings as described above.]

[0669] For compound (I-O-1p), compound (M-17-X) can be used instead of compound (M-9-X) and it can be produced according to Production Method 8.

[0670] Production Method 20

[0671] Compound (I-O-1p) can also be produced by subjecting the compound represented by formula (M-17-OH) (hereinafter referred to as compound (M-17-OH)) to intramolecular condensation in the presence of a condensing agent.

[0672] [Chemical formula 28]

[0673]

[0674] [In the formula, the symbols represent the same meanings as described above.]

[0675] For the compound (I-O-1p), the compound (M-17-OH) can be used in place of the compound (M-9-OH) and manufactured according to Production Method 9.

[0676] Production Method 21

[0677] The compound (I-O-1p) can also be manufactured by reacting the compound represented by the formula (M-18-X) (hereinafter referred to as the compound (M-18-X)) with a base.

[0678] [Chemical Formula 29]

[0679]

[0680] [In the formula, the symbols represent the same meanings as described above.]

[0681] For the compound (I-O-1p), the compound (M-18-X) can be used in place of the compound (M-10-X) and manufactured according to Production Method 10.

[0682] Production Method 22

[0683] The compound (I-O-1p) can also be manufactured by subjecting the compound represented by the formula (M-18-OH) (hereinafter referred to as the compound (M-18-OH)) to intramolecular condensation in the presence of a condensing agent.

[0684] [Chemical Formula 30]

[0685]

[0686] [In the formula, the symbols represent the same meanings as described above.]

[0687] For the compound (I-O-1p), the compound (M-18-OH) can also be used in place of the compound (M-10-OH) and manufactured according to Production Method 11.

[0688] Production Method 23

[0689] The N-oxide of the compound represented by the formula (I) can be manufactured by reacting the compound represented by the formula (I) with an oxidizing agent. The reaction can be carried out according to the methods described in, for example, Production Method 1, U.S. Patent Application Publication No. 2018 / 0009778 or International Publication No. 2016 / 121970.

[0690] Production Method 24

[0691] The compound represented by formula (I-O-1ph) (hereinafter referred to as compound (I-O-1ph)) can be produced by reacting the compound represented by formula (I-O-1pp) (hereinafter referred to as compound (I-O-1pp)) with the compound represented by formula (Ph-BOH) (hereinafter referred to as compound (Ph-BOH)) or the compound represented by formula (Ph-Bpin) (hereinafter referred to as compound (Ph-Bpin)) in the presence of a metal catalyst and a base.

[0692] [Chemical formula 31]

[0693]

[0694] [In the formula, R 4p represents a chlorine atom, a bromine atom or an iodine atom, R 4h represents a substituent selected from the group H 2 . y represents 0, 1, 2, 3, 4 or 5, and other symbols represent the same meanings as described above.]

[0695] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of them.

[0696] Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkali metal hydrides; and alkali metal phosphates such as potassium phosphate (hereinafter referred to as alkali metal phosphates).

[0697] Examples of the metal catalyst used in the reaction include nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

[0698] The reaction can also be carried out using a ligand as needed. Examples of the ligand include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, and N,N'-dimethylethylenediamine. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 0.5 moles relative to 1 mole of compound (I-O-1pp).

[0699] In the reaction, relative to 1 mole of the compound (I-O-1pp), the compound (Ph-BOH) or the compound (Ph-Bpin) is usually used in a ratio of 1 to 5 moles, the metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and the base is usually used in a ratio of 1 to 5 moles.

[0700] The reaction temperature is usually in the range of -20 °C to 150 °C. The reaction time is usually in the range of 0.5 to 24 hours.

[0701] After the reaction is completed, water can be added to the reaction mixture, and extraction is carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-O-1ph).

[0702] Production method 25

[0703] The compound represented by the formula (I-O-2ph) (hereinafter referred to as the compound (I-O-2ph)) can be produced by reacting the compound represented by the formula (I-O-2pp) (hereinafter referred to as the compound (I-O-2pp)) with the compound (Ph-BOH) or the compound (Ph-Bpin) in the presence of a metal catalyst and a base.

[0704] [Chemical formula 32]

[0705]

[0706] [In the formula, the symbols represent the same meanings as described above.]

[0707] For the compound (I-O-2ph), the compound (I-O-2pp) can be used instead of the compound (I-O-1pp), and it can be produced according to Production method 24.

[0708] Production method 26

[0709] The compound represented by the formula (I-O-1Ar) (hereinafter referred to as the compound (I-O-1Ar)) can be produced according to the following synthetic route.

[0710] [Chemical formula 33]

[0711]

[0712] [In the formula, A 1a represents CR 1a or a nitrogen atom, R 1a represents a hydrogen atom or a substituent selected from the group H 2 , and X h represents a halogen atom, and the other symbols represent the same meanings as described above.]

[0713] First, a method for producing a compound represented by formula (I-O-1-Bpin) (hereinafter referred to as compound (I-O-1-Bpin)) from a compound represented by formula (I-O-1pa) (hereinafter referred to as compound (I-O-1pa)) is described.

[0714] Compound (I-O-1-Bpin) can be produced by reacting compound (I-O-1pa) with bis(pinacolato)diboron in the presence of a metal catalyst and a base.

[0715] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[0716] Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrides, and alkali metal phosphates.

[0717] Examples of the metal catalyst used in the reaction include palladium catalysts such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II).

[0718] In the reaction, relative to 1 mole of compound (I-O-1pa), bis(pinacolato)diboron is usually used in a ratio of 1 to 3 moles, the metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and the base is usually used in a ratio of 1 to 5 moles.

[0719] The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.5 to 24 hours.

[0720] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain compound (I-O-1-Bpin).

[0721] Next, a method for producing compound (I-O-1Ar) from compound (I-O-1-Bpin) is described.

[0722] Compound (I-O-1Ar) can be produced by reacting compound (I-O-1-Bpin) with a compound represented by formula (Ar-hal) (hereinafter referred to as compound (Ar-hal)) in the presence of a metal catalyst and a base.

[0723] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of them.

[0724] Examples of the base used in the reaction include, for example, organic bases, alkali metal carbonates, alkali metal hydrides, and alkali metal phosphates.

[0725] Examples of the metal catalyst used in the reaction include, for example, palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

[0726] The reaction can also be carried out using a ligand as needed. Examples of the ligand include, for example, triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, and N,N'-dimethylethylenediamine. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (I-O-1-Bpin).

[0727] In the reaction, the compound (Ar-hal) is usually used in a proportion of 1 to 5 mol, the metal catalyst is usually used in a proportion of 0.01 to 0.5 mol, and the base is usually used in a proportion of 1 to 5 mol relative to 1 mol of the compound (I-O-1-Bpin).

[0728] The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.5 to 24 hours.

[0729] After completion of the reaction, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-O-1Ar).

[0730] Production Method 27

[0731] The compound represented by the formula (I-O-2Ar) (hereinafter referred to as the compound (I-O-2Ar)) can be produced according to the following synthetic route.

[0732] [Chemical Formula 34]

[0733]

[0734] [In the formula, the symbols represent the same meanings as described above.]

[0735] Regarding the compound (I-O-2Ar), the compound represented by the formula (I-O-2pa) can be used in place of the compound (I-O-1pa), and the compound represented by the formula (I-O-2-Bpin) produced according to Production Method 26 is produced according to Production Method 26.

[0736] Production Method 28

[0737] The compound represented by the formula (I-O-1NBoc) (hereinafter referred to as the compound (I-O-1NBoc)) can be produced by reacting the compound (I-O-1pp) with tert-butyl carbamate in the presence of a metal catalyst and a base.

[0738] [Chemical formula 35]

[0739]

[0740] [In the formula, the symbols represent the same meanings as described above.]

[0741] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[0742] Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrides, and alkali metal phosphates.

[0743] Examples of the metal catalyst used in the reaction include nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

[0744] The reaction can also be carried out using a ligand as needed. Examples of the ligand include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, and N,N'-dimethylethylenediamine. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 0.5 mol relative to 1 mol of the compound (I-O-1pp).

[0745] In the reaction, with respect to 1 mole of the compound (I-O-1pp), tert-butyl carbamate is usually used in a ratio of 1 to 5 moles, the metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and the base is usually used in a ratio of 1 to 5 moles.

[0746] The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.5 to 24 hours.

[0747] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then performed to obtain the compound (I-O-1NBoc).

[0748] Production Method 29

[0749] The compound represented by the formula (I-O-2NBoc) (hereinafter referred to as the compound (I-O-2NBoc)) can be produced by reacting the compound (I-O-2pp) with tert-butyl carbamate in the presence of a metal catalyst and a base.

[0750] [Chemical Formula 36]

[0751]

[0752] [In the formula, the symbols represent the same meanings as described above.]

[0753] For the compound (I-O-2NBoc), the compound (I-O-2pp) can be used instead of the compound (I-O-1pp), and it can be produced according to Production Method 28.

[0754] Production Method 30

[0755] The compound represented by the formula (I-O-1NH2) (hereinafter referred to as the compound (I-O-1NH2)) can be produced by reacting the compound (I-O-1NBoc) with an acid.

[0756] [Chemical Formula 37]

[0757]

[0758] [In the formula, the symbols represent the same meanings as described above.]

[0759] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons, ethers, alcohols, water, and mixtures of two or more of them.

[0760] Examples of the acid used in the reaction include inorganic acids such as hydrochloric acid; carboxylic acids such as trifluoroacetic acid.

[0761] In the reaction, relative to 1 mole of the compound (I-O-1NBoc), the acid is usually used in a ratio of 1 to 50 moles.

[0762] The reaction temperature is usually in the range of 0 °C to 120 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0763] After the reaction is completed, the reaction mixture can be extracted with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer can be carried out to obtain the compound (I-O-1NH2).

[0764] Production Method 31

[0765] The compound represented by the formula (I-O-2NH2) (hereinafter referred to as compound (I-O-2NH2)) can be produced by reacting the compound (I-O-2NBoc) with an acid.

[0766] [Chemical Formula 38]

[0767]

[0768] [In the formula, the symbols represent the same meanings as described above.]

[0769] For the compound (I-O-2NH2), the compound (I-O-2NBoc) can be used instead of the compound (I-O-1NBoc) and produced according to Production Method 30.

[0770] Production Method 32

[0771] The compound represented by the formula (I-O-1-NHamide) (hereinafter referred to as compound (I-O-1-NHamide)) can be produced by reacting the compound (I-O-1NH2) with the compound represented by the formula (R-13) (hereinafter referred to as compound (R-13)).

[0772] [Chemical Formula 39]

[0773]

[0774] [In the formula, R Alkyl represents a C1-C6 chain hydrocarbon group that may be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that may be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that may be substituted by one or more halogen atoms, a phenyl group that may be substituted by one or more substituents selected from Group D 2 or a 5- or 6-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from Group D 2 , and the other symbols represent the same meanings as described above.]

[0775] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers; aliphatic hydrocarbons such as hexane, heptane, and octane (hereinafter referred to as aliphatic hydrocarbons); aromatic hydrocarbons; halogenated hydrocarbons; esters; nitriles; aprotic polar solvents; nitrogen-containing aromatic compounds; and mixtures of two or more of them.

[0776] In the reaction, a base can be used as needed. Examples of the base used in the reaction include alkali metal carbonates; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter referred to as alkali metal hydroxides); and organic bases. When a base is used in the reaction, the base is usually used in a ratio of 1 to 2 moles relative to 1 mole of the compound (I-O-1NH2).

[0777] In the reaction, the compound (R-13) is usually used in a ratio of 0.8 to 2 moles relative to 1 mole of the compound (I-O-1NH2).

[0778] The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 24 hours.

[0779] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-O-1-NHamide).

[0780] The compound (R-13) is a commercially available compound or can be manufactured by known methods.

[0781] Production Method 33

[0782] The compound represented by the formula (I-O-2-NHamide) (hereinafter referred to as the compound (I-O-2-NHamide)) can be produced by reacting the compound (I-O-2NH2) with the compound (R-13).

[0783] [Chemical formula 40]

[0784]

[0785] [In the formula, the symbols represent the same meanings as described above.]

[0786] For the compound (I-O-2-NHamide), the compound (I-O-2NH2) can be used instead of the compound (I-O-1NH2), and it can be produced according to Production Method 32.

[0787] Production Method 34

[0788] The compound represented by the formula (I-O-1-amide) (hereinafter referred to as compound (I-O-1-amide)) can be produced by reacting compound (I-O-1-NHamide) with compound (R-14) in the presence of a base.

[0789] [Chemical formula 41]

[0790]

[0791] [In the formula, L2 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, etc., and R amide represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and the other symbols have the same meanings as described above.]

[0792] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[0793] Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[0794] In the reaction, relative to 1 mole of compound (I-O-1-NHamide), compound (R-14) is usually used in a ratio of 1 to 5 moles, and the base is usually used in a ratio of 1 to 5 moles.

[0795] The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours.

[0796] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are carried out to obtain compound (I-O-1-amide).

[0797] Compound (R-14) is a commercially available compound or can be produced by a known method.

[0798] Production method 35

[0799] The compound represented by the formula (I-O-2-amide) (hereinafter referred to as compound (I-O-2-amide)) can be produced by reacting compound (I-O-2-NHamide) with compound (R-14) in the presence of a base.

[0800] [Chemical formula 42]

[0801]

[0802] [In the formula, the symbols have the same meanings as described above.]

[0803] In the case of the compound (I-O-2-amide), the compound (I-O-2-NHamide) can be used instead of the compound (I-O-1-NHamide) and manufactured according to Production Method 34.

[0804] Production Method 36

[0805] The compound represented by the formula (I-O-1-OH) (hereinafter referred to as compound (I-O-1-OH)) can be manufactured by reacting the compound (I-O-1-OBn) with hydrogen in the presence of a catalyst.

[0806] [Chemical Formula 43]

[0807]

[0808] [In the formula, the symbols represent the same meanings as described above.]

[0809] In the reaction, hydrogen gas can be used. The pressure of hydrogen gas is usually 1 to 100 atmospheres.

[0810] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, esters, alcohols, water, and mixtures of two or more thereof.

[0811] Examples of the catalyst used in the reaction include transition metal compounds such as palladium on carbon, palladium(II) hydroxide, Raney nickel, and platinum oxide.

[0812] In the reaction, the catalyst is usually used in a proportion of 0.001 to 0.5 mol relative to 1 mol of the compound (I-O-1-OBn).

[0813] The reaction can also be carried out using an acid, a base, etc. as needed.

[0814] Examples of the acid include acetic acid, hydrochloric acid, etc., and examples of the base include tertiary amines such as triethylamine. When an acid is used in the reaction, the acid is usually used in a proportion of 0.001 to 0.5 mol relative to 1 mol of the compound (I-O-1-OBn). When a base is used in the reaction, the base is usually used in a proportion of 0.1 to 5 mol relative to 1 mol of the compound (I-O-1-OBn).

[0815] The reaction temperature is usually in the range of -20°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours.

[0816] After the reaction is completed, the reaction mixture can be filtered, extracted with an organic solvent as needed, and post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-O-1-OH).

[0817] Production method 37

[0818] The compound represented by formula (I-O-2-OH) (hereinafter referred to as compound (I-O-2-OH)) can be produced by reacting compound (I-O-2-OBn) with hydrogen in the presence of a catalyst.

[0819] [Chemical formula 44]

[0820]

[0821] [In the formula, the symbols represent the same meanings as described above.]

[0822] For compound (I-O-2-OH), compound (I-O-2-OBn) can be used instead of compound (I-O-1-OBn), and it can be produced according to production method 36.

[0823] Production method 38

[0824] The compound represented by formula (I-O-1-OAlkyl) (hereinafter referred to as compound (I-O-1-OAlkyl)) can be produced by reacting compound (I-O-1-OH) with the compound represented by formula (R-15) (hereinafter referred to as compound (R-15)) in the presence of a base.

[0825] [Chemical formula 45]

[0826]

[0827] [In the formula, L3 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, etc., and R OH represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F 2 , a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group J 2 , a C3-C7 cycloalkenyl group which may be substituted with one or more substituents selected from group J 2 , a phenyl group which may be substituted with one or more substituents selected from group D 2 , or a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group D 2 , and other symbols represent the same meanings as described above.]

[0828] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[0829] Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[0830] In the reaction, relative to 1 mole of the compound (I-O-1-OH), the compound (R-15) is usually used in a ratio of 1 to 5 moles, and the base is usually used in a ratio of 1 to 5 moles.

[0831] The reaction temperature is usually in the range of 0 °C to 100 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0832] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (I-O-1-OAlkyl).

[0833] The compound (R-15) is a commercially available compound or can be manufactured using known methods.

[0834] Manufacturing method 39

[0835] The compound represented by the formula (I-O-2-OAlkyl) (hereinafter referred to as the compound (I-O-2-OAlkyl)) can be manufactured by reacting the compound (I-O-2-OH) with the compound (R-15) in the presence of a base.

[0836] [Chemical formula 46]

[0837]

[0838] [In the formula, the symbols represent the same meanings as described above.]

[0839] For the compound (I-O-2-OAlkyl), the compound (I-O-2-OH) can be used instead of the compound (I-O-1-OH), and it can be manufactured according to Manufacturing method 38.

[0840] Hereinafter, the manufacturing methods of the intermediates are described.

[0841] Reference manufacturing method 1

[0842] The compound represented by the formula (M-2-n1) and the compound represented by the formula (M-2-n2) can be manufactured by reacting the compound represented by the formula (M-2-n0) with an oxidizing agent.

[0843] [Chemical formula 47]

[0844]

[0845] [In the formula, the symbols represent the same meanings as described above.]

[0846] These reactions can be carried out according to Manufacturing method 1.

[0847] Reference manufacturing method 2

[0848] The compound represented by the formula (M-2-d) (hereinafter referred to as compound (M-2-d)) can be produced according to the following synthetic route.

[0849] [Chemical formula 48]

[0850]

[0851] [In the formula, X c represents a chlorine atom or a bromine atom, R 52 represents a hydrogen atom, a methyl group or an ethyl group, and other symbols represent the same meanings as described above.]

[0852] The compound represented by the formula (M-20) (hereinafter referred to as compound (M-20)) can be produced by reacting the compound represented by the formula (M-19) (hereinafter referred to as compound (M-19)) with the compound represented by the formula (R-6) (hereinafter referred to as compound (R-6)).

[0853] The reaction is usually carried out in a solvent. Examples of the solvent include aromatic hydrocarbons, alcohols, nitriles, and mixtures of two or more of them.

[0854] In the reaction, relative to 1 mole of the compound (R-6), the compound (M-19) is usually used in a ratio of 1 to 10 moles.

[0855] The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 0.1 to 48 hours.

[0856] After the reaction is completed, usual post-treatment operations can be carried out to obtain the compound (M-20).

[0857] The compound (R-6) and the compound (M-19) are commercially available compounds or can be produced by known methods.

[0858] The compound represented by the formula (M-21) (hereinafter referred to as compound (M-21)) can be produced by reacting the compound (M-20) with the compound represented by the formula (R-7) (hereinafter referred to as compound (R-7)).

[0859] The reaction is usually carried out in a solvent. Examples of the solvent include aromatic hydrocarbons, nitriles, and mixtures of two or more of them.

[0860] In the reaction, relative to 1 mole of the compound (M-20), the compound (R-7) is usually used in a ratio of 1 to 10 moles.

[0861] The reaction temperature is usually in the range of 60°C to 120°C. The reaction time is usually in the range of 0.1 to 48 hours.

[0862] After the reaction is completed, usual post-treatment operations can be carried out, and thus compound (M-21) can be obtained.

[0863] Compound (R-7) is a commercially available compound or can be manufactured by known methods.

[0864] The compound represented by formula (M-22) (hereinafter referred to as compound (M-22)) can be manufactured by reacting compound (M-21) with N-iodosuccinimide. The reaction can be carried out according to the method for manufacturing compound (M-6) from compound (M-5) in Production Method 6.

[0865] Compound (M-2-d) can be manufactured by reacting compound (M-21) or compound (M-22) with compound (R-1). These reactions can be carried out according to the method for manufacturing compound (I-n0-1) from compound (M-5) or compound (M-6) in Production Method 6.

[0866] Reference Production Method 3

[0867] The compound represented by formula (M-2-f) can be manufactured by reacting the compound represented by formula (M-2-e) (hereinafter referred to as compound (M-2-e)) with silver fluoride in the presence of a metal catalyst.

[0868] [Chemical formula 49]

[0869]

[0870] [In the formula, the symbols represent the same meanings as described above.]

[0871] The reaction can be carried out according to the method described, for example, in Journal of the American Chemical Society, 2014, 136, 3792.

[0872] Reference Production Method 4

[0873] The compound represented by formula (M-2-g) can be manufactured by reacting compound (M-2-e) with sodium iodide in the presence of a metal catalyst.

[0874] [Chemical formula 50]

[0875]

[0876] [In the formula, the symbols represent the same meanings as described above.]

[0877] The reaction can be carried out according to the method described in, for example, Journal of the American Chemical Society, 2002, 124, 14844.

[0878] Refer to Manufacturing Method 5

[0879] Compound (M-9-X) can be produced by reacting a compound represented by formula (M-23) (hereinafter referred to as compound (M-23)) with a compound represented by formula (M-24) (hereinafter referred to as compound (M-24)) in the presence of a condensing agent.

[0880] [Chemical formula 51]

[0881]

[0882] [In the formula, the symbols represent the same meanings as described above.]

[0883] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, halogenated hydrocarbons, aromatic hydrocarbons, esters, nitriles, aprotic polar solvents, nitrogen-containing aromatic compounds, and mixtures of two or more of them.

[0884] Examples of the condensing agent used in the reaction include carbodiimide compounds such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide.

[0885] In the reaction, a catalyst can be used as needed. Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole. When a catalyst is used in the reaction, it is usually used in a proportion of 0.01 to 0.5 moles relative to 1 mole of compound (M-24).

[0886] In the reaction, a base can be used as needed. Examples of the base include organic bases. When a base is used in the reaction, it is usually used in a proportion of 1 to 2 moles relative to 1 mole of compound (M-24).

[0887] In the reaction, compound (M-23) is usually used in a proportion of 1 to 2 moles and the condensing agent is usually used in a proportion of 1 to 2 moles relative to 1 mole of compound (M-24).

[0888] The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 0.1 to 12 hours.

[0889] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then carried out to obtain compound (M-9-X).

[0890] Reference production method 6

[0891] Compound (M-23) can be produced by hydrolyzing the compound represented by formula (M-25) (hereinafter referred to as compound (M-25)).

[0892] [Chemical formula 52]

[0893]

[0894] [In the formula, R A represents a C1-C3 alkyl group such as a methyl group or an ethyl group, and other symbols have the same meanings as described above.]

[0895] In the case of hydrolysis using an acid, the reaction is usually carried out using an aqueous solution of the acid as a solvent.

[0896] Examples of the acid used in the reaction include inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid; and carboxylic acids such as acetic acid and trifluoroacetic acid.

[0897] The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours.

[0898] After completion of the reaction, extraction can be carried out using an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are performed to obtain compound (M-23).

[0899] In the case of hydrolysis using a base, the reaction is usually carried out in the presence of a solvent.

[0900] Examples of the solvent used in the reaction include ethers, alcohols, water, and mixtures of two or more of them.

[0901] Examples of the base used in the reaction include alkali metal hydroxides.

[0902] In the reaction, the base is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-25).

[0903] The reaction temperature is usually in the range of 0°C to 120°C. The reaction time is usually in the range of 0.1 to 24 hours.

[0904] After completion of the reaction, the reaction solution can be made acidic, and then the reaction mixture is extracted using an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are performed to obtain compound (M-23).

[0905] Reference production method 7

[0906] Compound (M-25) can be produced by reacting a compound represented by formula (M-26) (hereinafter referred to as compound (M-26)) with a compound represented by formula (R-8) (hereinafter referred to as compound (R-8)) in the presence of a condensing agent.

[0907] [Chemical formula 53]

[0908]

[0909] [In the formula, the symbols have the same meanings as described above.]

[0910] The reaction is usually carried out in a solvent. Examples of the solvent include ethers, halogenated hydrocarbons, aromatic hydrocarbons, esters, nitriles, aprotic polar solvents, nitrogen-containing aromatic compounds, and mixtures of two or more of them.

[0911] Examples of the condensing agent used in the reaction include a mixture of triphenylphosphine and an azo diester compound. Examples of the azo diester compound include diethyl azodicarboxylate.

[0912] In the reaction, relative to 1 mole of compound (M-26), compound (R-8) is usually used in a ratio of 1 to 5 moles, and the condensing agent is usually used in a ratio of 1 to 5 moles.

[0913] The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 24 hours.

[0914] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then carried out to obtain compound (M-25).

[0915] Compound (M-26) is a commercially available compound or can be produced by known methods.

[0916] Compound (R-8) is a commercially available compound or can be produced by known methods.

[0917] Reference production method 8

[0918] Compound (M-24) can be produced by reacting compound (M-2-h) with ammonia.

[0919] [Chemical formula 54]

[0920]

[0921] [In the formula, X e represents a fluorine atom or a chlorine atom, and the other symbols have the same meanings as described above.]

[0922] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, nitriles, aprotic polar solvents, alcohols, water, and mixtures of two or more of them.

[0923] In the reaction, a base can be used as needed. Examples of the base used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used in a proportion of 0.1 to 5 moles relative to 1 mole of the compound (M-2-h).

[0924] Ammonia can also be used in the form of solutions such as aqueous ammonia and ammonia-methanol solution.

[0925] In the reaction, ammonia is usually used in a proportion of 1 to 100 moles relative to 1 mole of the compound (M-2-h).

[0926] The reaction temperature is usually in the range of -20°C to 100°C. The reaction time is usually in the range of 0.1 to 48 hours.

[0927] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out with an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (M-24).

[0928] Reference Production Method 9

[0929] The compound (M-9-X) can also be produced by reacting the compound represented by the formula (M-27) (hereinafter referred to as the compound (M-27)) with the compound (M-24).

[0930] [Chemical Formula 55]

[0931]

[0932] [In the formula, the symbols represent the same meanings as described above.]

[0933] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers; aliphatic hydrocarbons; aromatic hydrocarbons; halogenated hydrocarbons; esters; nitriles; aprotic polar solvents, and mixtures of two or more of them.

[0934] In the reaction, a base can be used as needed. Examples of the base used in the reaction include alkali metal carbonates; alkali metal hydroxides; and organic bases. When a base is used in the reaction, the base is usually used in a proportion of 1 to 2 moles relative to 1 mole of the compound (M-24).

[0935] In the reaction, the compound (M-27) is usually used in a proportion of 0.8 to 1.2 moles relative to 1 mole of the compound (M-24).

[0936] The reaction temperature is generally in the range of -20°C to 200°C. The reaction time is generally in the range of 0.1 to 24 hours.

[0937] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then performed to obtain the compound (M-9-X).

[0938] Reference Production Method 10

[0939] Compound (M-27) can be produced by reacting compound (M-23) in the presence of a chlorinating agent.

[0940] [Chemical Formula 56]

[0941]

[0942] [In the formula, the symbols represent the same meanings as described above.]

[0943] The reaction is generally carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, halogenated hydrocarbons, and mixtures of two or more of them.

[0944] Examples of the chlorinating agent used in the reaction include thionyl chloride, oxalyl chloride, phosphoryl chloride, etc.

[0945] In the reaction, relative to 1 mole of compound (M-23), the chlorinating agent is generally used in a ratio of 1 to 5 moles.

[0946] The reaction temperature is generally in the range of 0°C to 100°C. The reaction time is generally in the range of 0.1 to 24 hours.

[0947] After the reaction is completed, the solvent can be distilled off to obtain compound (M-27).

[0948] Reference Production Method 11

[0949] Compound (M-9-OH) can be produced by reacting the compound represented by formula (M-9-P) (hereinafter referred to as compound (M-9-P)) with an acid.

[0950] [Chemical Formula 57]

[0951]

[0952] [In the formula, X B represents OR B , R BIt represents a protecting group such as tetrahydropyranyl, methoxymethyl, 2-methoxyethoxymethyl, tert-butyldimethylsilyl or tribenzylsilyl, and other symbols represent the same meanings as those described above.

[0953] The reaction is usually carried out in a solvent. As the solvent used in the reaction, for example, ethers, alcohols, water, and mixtures of two or more of them can be mentioned.

[0954] As the acid used in the reaction, for example, inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid; carboxylic acids such as acetic acid, trifluoroacetic acid can be mentioned.

[0955] The reaction temperature is usually in the range of 0 °C to 120 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0956] In the reaction, relative to 1 mole of the compound (M-9-P), the acid is usually used in a ratio of 1 to 10 moles.

[0957] After the reaction is completed, the reaction mixture can be extracted with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (M-9-OH).

[0958] Reference Production Method 12

[0959] The compound (M-9-P) can be produced by reacting the compound represented by the formula (M-28) (hereinafter referred to as the compound (M-28)) with the compound (M-24) in the presence of a condensing agent.

[0960] [Chemical Formula 58]

[0961]

[0962] [In the formula, the symbols represent the same meanings as those described above.]

[0963] For the compound (M-9-P), the compound (M-28) can be used instead of the compound (M-23), and it can be produced according to Reference Production Method 5.

[0964] Reference Production Method 13

[0965] The compound (M-28) can be produced by hydrolyzing the compound represented by the formula (M-29) (hereinafter referred to as the compound (M-29)) in the presence of a base.

[0966] [Chemical Formula 59]

[0967]

[0968] [In the formula, the symbols represent the same meanings as those described above.]

[0969] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include, for example, ethers, alcohols, water, and mixtures of two or more of them.

[0970] Examples of the base used in the reaction include, for example, alkali metal hydroxides.

[0971] In the reaction, the base is usually used in a ratio of 1 to 10 moles relative to 1 mole of the compound (M-29).

[0972] The reaction temperature is usually in the range of 0 °C to 120 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[0973] After the reaction is completed, the reaction solution can be made acidic, and then the reaction mixture is extracted with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (M-28).

[0974] Reference Production Method 14

[0975] The compound (M-29) can be produced by reacting the compound (M-26) with the compound represented by the formula (R-9) (hereinafter referred to as the compound (R-9)) in the presence of a condensing agent.

[0976] [Chemical Formula 60]

[0977]

[0978] [In the formula, the symbols represent the same meanings as described above.]

[0979] For the compound (M-29), the compound (R-9) can be used instead of the compound (R-8), and it can be produced according to Reference Production Method 7.

[0980] The compound (R-9) is a commercially available compound or can be produced by a known method.

[0981] Reference Production Method 15

[0982] The compound (M-10-X) can be produced by reacting the compound (M-10-OH) in the presence of a halogenating agent.

[0983] [Chemical Formula 61]

[0984]

[0985] [In the formula, the symbols represent the same meanings as described above.]

[0986] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, alcohols, aromatic hydrocarbons, halogenated hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of them.

[0987] Examples of the halogenating agent used in the reaction include hydrogen halides such as hydrogen chloride; phosphorus halides such as phosphorus tribromide; thionyl halides such as thionyl chloride; a mixture of triphenylphosphine and carbon tetrachloride; a mixture of triphenylphosphine and carbon tetrabromide, etc.

[0988] In the reaction, the halogenating agent is usually used in a ratio of 1 to 10 moles relative to 1 mole of the compound (M-10-OH).

[0989] In the reaction, a base can be used as needed. Examples of the base used in the reaction include organic bases. When a base is used in the reaction, the base is usually used in a ratio of 1 to 2 moles relative to 1 mole of the compound (M-10-OH).

[0990] The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.1 to 24 hours.

[0991] After the reaction is completed, water can be added to the reaction mixture, extraction can be carried out using an organic solvent, and post-treatment operations such as drying and concentrating the organic layer can be carried out to obtain the compound (M-10-X).

[0992] Reference Production Method 16

[0993] The compound (M-10-OH) can be produced by reacting the compound represented by the formula (M-10-P) (hereinafter, the compound (M-10-P)) with an acid.

[0994] [Chemical Formula 62]

[0995]

[0996] [In the formula, the symbols represent the same meanings as described above.]

[0997] For the compound (M-10-OH), the compound (M-10-P) can be used instead of the compound (M-9-P), and it can be produced according to Reference Production Method 11.

[0998] Reference Production Method 17

[0999] The compound (M-10-P) can be produced by reacting the compound represented by the formula (M-30) (hereinafter referred to as the compound (M-30)) with the compound represented by the formula (M-33) (hereinafter referred to as the compound (M-33)) in the presence of a condensing agent.

[1000] [Chemical Formula 63]

[1001]

[1002] [In the formula, the symbols represent the same meanings as described above.]

[1003] Regarding the compound (M-10-P), the compound (M-30) can be used instead of the compound (M-23), and the compound (M-33) can be used instead of the compound (M-24), and it can be produced according to the reference production method 5.

[1004] The compound (M-30) is a commercially available compound or can be produced by known methods.

[1005] Reference Production Method 18

[1006] The compound (M-10-P) can also be produced by reacting the compound represented by the formula (M-32) (hereinafter referred to as the compound (M-32)) with the compound (M-33).

[1007] [Chemical Formula 64]

[1008]

[1009] [In the formula, the symbols represent the same meanings as described above.]

[1010] Regarding the compound (M-10-P), the compound (M-32) can be used instead of the compound (M-27), and the compound (M-33) can be used instead of the compound (M-24), and it can be produced according to the reference production method 9.

[1011] The compound (M-32) is a commercially available compound or can be produced by known methods.

[1012] Reference Production Method 19

[1013] The compound (M-33) can be produced by reacting the compound (M-24) with the compound represented by the formula (R-12) (hereinafter referred to as the compound (R-12)) in the presence of a base.

[1014] [Chemical Formula 65]

[1015]

[1016] [In the formula, L represents a leaving group such as a chlorine atom or a bromine atom, and the other symbols represent the same meanings as described above.]

[1017] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[1018] Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[1019] In the reaction, relative to 1 mole of compound (M-24), compound (R-12) is usually used in a ratio of 1 to 5 moles, and the base is usually used in a ratio of 1 to 2 moles.

[1020] The reaction temperature is usually in the range of 0 °C to 100 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[1021] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then carried out to obtain compound (M-33).

[1022] Compound (R-12) is a commercially available compound or can be manufactured by known methods.

[1023] Reference Manufacturing Method 20

[1024] Compound (M-2-n0) can be manufactured according to the following synthetic route.

[1025] [Chemical Formula 66]

[1026]

[1027] [In the formula, X b represents SR 2 or a hydrogen atom, and X f represents a chlorine atom, a bromine atom, or an iodine atom, and other symbols have the same meanings as described above.]

[1028] First, the process of manufacturing the compound represented by formula (M-4-f) (hereinafter referred to as compound (M-4-f)) from compound (M-4) is described.

[1029] Compound (M-4-f) can be manufactured by reacting compound (M-4) with a halogenating agent.

[1030] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of them.

[1031] Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, etc.

[1032] In the reaction, the halogenating agent is usually used in a proportion of 1 to 20 moles relative to 1 mole of the compound (M-4).

[1033] The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours.

[1034] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. Post-treatment operations such as drying and concentrating the organic layer are then carried out to obtain the compound (M-4-f).

[1035] Next, the process for producing the compound (M-2-n0) from the compound (M-4-f) is described.

[1036] The compound (M-2-n0) can be produced by reacting the compound (M-4-f) with the compound (R-1) in the presence of a metal catalyst and a base.

[1037] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of them.

[1038] Examples of the metal catalyst used in the reaction include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), tris(dibenzylideneacetone)dipalladium(0), palladium(II) acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0), nickel(II) chloride; and copper catalysts such as copper(I) iodide, copper(I) chloride.

[1039] Examples of the base used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases.

[1040] In the reaction, a ligand can also be used. Examples of the ligand include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, etc. When a ligand is used in the reaction, the ligand is usually used in a proportion of 0.01 to 1 mole relative to 1 mole of the compound (M-4-f).

[1041] In the reaction, relative to 1 mole of compound (M-4-f), compound (R-1) is usually used in a ratio of 1 to 20 moles, the metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and the base is usually used in a ratio of 0.1 to 5 moles.

[1042] The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours.

[1043] After the reaction is completed, water can be added to the reaction mixture, extraction can be carried out using an organic solvent, and post-treatment operations such as drying and concentrating the organic layer can be performed to obtain compound (M-2-n0).

[1044] Next, the process for producing compound (M-2-n0) from compound (M-4) is described.

[1045] Compound (M-2-n0) can also be produced by reacting compound (M-4) with the compound represented by formula (R-3) (hereinafter referred to as compound (R-3)) in the presence of a halogenating agent.

[1046] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of them.

[1047] Examples of the halogenating agent include bromine, iodine, sodium bromide, potassium bromide, sodium iodide, potassium iodide, etc.

[1048] In the reaction, an oxidizing agent can be used as needed. Examples of the oxidizing agent used in the reaction include hydrogen peroxide, tert-butyl hydroperoxide, DMSO, etc. When an oxidizing agent is used in the reaction, relative to 1 mole of compound (M-4), the oxidizing agent is usually used in a ratio of 1 to 20 moles.

[1049] In the reaction, relative to 1 mole of compound (M-4), compound (R-3) is usually used in a ratio of 0.5 to 10 moles, and the halogenating agent is usually used in a ratio of 0.05 to 10 moles.

[1050] The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours.

[1051] After the reaction is completed, water can be added to the reaction mixture, extraction can be carried out using an organic solvent, and post-treatment operations such as drying and concentrating the organic layer can be performed to obtain compound (M-2-n0).

[1052] Compound (R-3) is known or can be produced according to known methods.

[1053] The compound (M-4) is known or can be produced according to the methods described in WO2015 / 157093, WO2016 / 109706, Organic & Biomolecular Chemistry, 2017, 15, 4199., and European Journal of Medicinal Chemistry, 2016, 123, 916., etc.

[1054] Reference Production Method 21

[1055] The compound represented by the formula (M-11-n1) (hereinafter referred to as compound (M-11-n1)) or the compound represented by the formula (M-11-n2) (hereinafter referred to as compound (M-11-n2)) can be produced by reacting the compound (M-11-n0) with an oxidizing agent. The compound (M-11-n2) can also be produced by reacting the compound (M-11-n1) with an oxidizing agent.

[1056] [Chemical Formula 67]

[1057]

[1058] [In the formula, the symbols have the same meanings as described above.]

[1059] These reactions can be carried out according to Production Method 1.

[1060] Reference Production Method 22

[1061] The compound (M-17-X) can be produced by reacting the compound (M-23) with the compound represented by the formula (M-34) (hereinafter referred to as compound (M-34)) in the presence of a condensing agent.

[1062] [Chemical Formula 68]

[1063]

[1064] [In the formula, the symbols have the same meanings as described above.]

[1065] For the compound (M-17-X), the compound (M-34) can be used instead of the compound (M-24) and produced according to Reference Production Method 5.

[1066] Reference Production Method 23

[1067] The compound (M-17-X) can also be produced by reacting the compound (M-27) with the compound (M-34).

[1068] [Chemical Formula 69]

[1069]

[1070] [In the formula, the symbol represents the same meaning as described above.]

[1071] For the compound (M-17-X), the compound (M-34) can be used instead of the compound (M-24) and produced according to the reference production method 9.

[1072] Reference production method 24

[1073] The compound (M-34) can be produced by reacting the compound represented by the formula (M-11-h) (hereinafter referred to as the compound (M-11-h)) with ammonia.

[1074] [Chemical formula 70]

[1075]

[1076] [In the formula, the symbol represents the same meaning as described above.]

[1077] For the compound (M-34), the compound (M-11-h) can be used instead of the compound (M-2-h) and produced according to the reference production method 8.

[1078] Reference production method 25

[1079] The compound (M-11-n0) can be produced according to the following synthetic route.

[1080] [Chemical formula 71]

[1081]

[1082] [In the formula, the symbol represents the same meaning as described above.]

[1083] These reactions can be carried out according to the reference production method 20.

[1084] Reference production method 26

[1085] The compound (M-17-OH) can be produced by reacting the compound represented by the formula (M-17-P) (hereinafter referred to as the compound (M-17-P)) with an acid.

[1086] [Chemical formula 72]

[1087]

[1088] [In the formula, the symbol represents the same meaning as described above.]

[1089] For the compound (M-17-OH), the compound (M-17-P) can be used instead of the compound (M-9-P) and manufactured according to the reference manufacturing method 11.

[1090] Reference manufacturing method 27

[1091] The compound (M-17-P) can be manufactured by reacting the compound represented by the formula (M-28) (hereinafter referred to as the compound (M-28)) with the compound (M-34) in the presence of a condensing agent.

[1092] [Chemical formula 73]

[1093]

[1094] [In the formula, the symbols represent the same meanings as described above.]

[1095] For the compound (M-17-P), the compound (M-34) can be used instead of the compound (M-24) and manufactured according to the reference manufacturing method 12.

[1096] Reference manufacturing method 28

[1097] The compound (M-18-OH) can be manufactured by reacting the compound represented by the formula (M-18-P) (hereinafter referred to as the compound (M-18-P)) with an acid.

[1098] [Chemical formula 74]

[1099]

[1100] [In the formula, the symbols represent the same meanings as described above.]

[1101] For the compound (M-18-OH), the compound (M-18-P) can be used instead of the compound (M-9-P) and manufactured according to the reference manufacturing method 11.

[1102] Reference manufacturing method 29

[1103] The compound (M-18-P) can be manufactured by reacting the compound (M-30) with the compound represented by the formula (M-35) (hereinafter referred to as the compound (M-35)) in the presence of a condensing agent.

[1104] [Chemical formula 75]

[1105]

[1106] [In the formula, the symbols represent the same meanings as described above.]

[1107] Regarding the compound (M-18-P), the compound (M-30) can be used in place of the compound (M-23), and the compound (M-35) can be used in place of the compound (M-24), and it can be produced according to the reference production method 5.

[1108] Reference production method 30

[1109] The compound (M-18-P) can also be produced by reacting the compound (M-32) with the compound (M-35).

[1110] [Chemical formula 76]

[1111]

[1112] [In the formula, the symbols represent the same meanings as described above.]

[1113] Regarding the compound (M-18-P), the compound (M-32) can be used in place of the compound (M-27), and the compound (M-35) can be used in place of the compound (M-24), and it can be produced according to the reference production method 9.

[1114] Reference production method 31

[1115] The compound (M-35) can be produced by reacting the compound (M-34) with the compound (R-12) in the presence of a base.

[1116] [Chemical formula 77]

[1117]

[1118] [In the formula, the symbols represent the same meanings as described above.]

[1119] Regarding the compound (M-35), the compound (M-34) can be used in place of the compound (M-24), and it can be produced according to the reference production method 19.

[1120] Reference production method 32

[1121] The compound (M-18-X) can be produced by reacting the compound (M-18-OH) in the presence of a halogenating agent.

[1122] [Chemical formula 78]

[1123]

[1124] [In the formula, the symbols represent the same meanings as described above.]

[1125] Regarding the compound (M-18-X), the compound (M-18-OH) can be used in place of the compound (M-10-OH), and it can be produced according to the reference production method 15.

[1126] Compound (M-2) can also be produced according to the method described in, for example, International Publication No. 2020 / 158889.

[1127] Reference Production Method 33

[1128] Compound (M-1) can also be produced according to the following synthetic route.

[1129] [Chemical Formula 79]

[1130]

[1131] [In the formula, X P represents a protecting group such as tert-butoxycarbonyl, and the other symbols have the same meanings as described above.]

[1132] First, a method for producing a compound represented by the formula (M-29-N) (hereinafter referred to as compound (M-29-N)) from a compound represented by the formula (M-29-N-PG) (hereinafter referred to as compound (M-29-N-PG)) will be described.

[1133] Compound (M-29-N) can be produced by reacting compound (M-29-N-PG) with an acid.

[1134] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[1135] Examples of the acid used in the reaction include inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid; carboxylic acids such as acetic acid and trifluoroacetic acid.

[1136] In the reaction, the acid is usually used in a ratio of 1 to 30 moles relative to 1 mole of compound (M-29-N-PG).

[1137] The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours.

[1138] After the reaction is completed, post-treatment operations such as concentrating the reaction mixture can be carried out to obtain compound (M-29-N).

[1139] Next, a method for producing compound (M-1) from compound (M-29-N) will be described.

[1140] Compound (M-1) can be produced by reacting compound (M-29-N) with a base.

[1141] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of them.

[1142] Examples of the base used in the reaction include alkali metal carbonates.

[1143] In the reaction, relative to 1 mole of the compound (M-29-N), the base is usually used in a ratio of 1 to 30 moles.

[1144] The reaction temperature is usually in the range of 0 °C to 100 °C. The reaction time is usually in the range of 0.1 to 24 hours.

[1145] After the reaction is completed, water can be added to the reaction mixture, and extraction can be carried out using an organic solvent. After-treatment operations such as drying and concentrating the organic layer are carried out to obtain the compound (M-1).

[1146] The compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of the following group (a), group (b), group (c), and group (d) (hereinafter referred to as this component).

[1147] The above-mentioned mixing or combination means that the compound of the present invention and this component are used simultaneously, separately, or at intervals.

[1148] When the compound of the present invention and this component are used simultaneously, the compound of the present invention and this component can be contained in separate preparations, or can be contained in the same preparation.

[1149] One aspect of the present invention is a composition (hereinafter referred to as composition A) containing one or more components selected from the group consisting of group (a), group (b), group (c), and group (d) (i.e., this component), and the compound of the present invention.

[1150] Group (a) is a group consisting of acetylcholinesterase inhibitors (such as carbamate pesticides, organophosphorus pesticides), GABA-gated chloride channel blockers (such as phenylpyrazole pesticides), sodium channel modulators (such as pyrethroid pesticides), nicotinic acetylcholine receptor competitive modulators (such as neonicotinoid pesticides), allosteric modulators of nicotinic acetylcholine receptors, allosteric modulators of glutamate-gated chloride channels (such as macrolide pesticides), juvenile hormone mimetics, multi-site inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, insect midgut intima disruptors derived from microorganisms, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (such as nereistoxin pesticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (such as diamide pesticides), chordotonal organ modulators, microbial pesticides, and other insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients. These ingredients are described according to the classification based on the mode of action of IRAC.

[1151] Group (b) is a group consisting of nucleic acid synthesis inhibitors (such as phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (such as MBC fungicides), respiratory inhibitors (such as QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (such as anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (such as DMI fungicides of the triazole series, etc.), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides and other fungicidal active ingredients. These ingredients are described according to the classification based on the mode of action of FRAC.

[1152] Group (c) is a group of plant growth regulating components (including mycorrhizal fungi and rhizobia).

[1153] Group (d) is a group of repellent components.

[1154] Examples of combinations of these components with the compounds of the present invention are described below. For example, alanycarb + SX means the combination of alanycarb and SX.

[1155] It should be noted that the abbreviation of SX refers to any one of the compounds of the present invention selected from the compound groups SX1 to SX1840. In addition, the components described below are all known components, which can be obtained from commercially available preparations or manufactured by known methods. When the component is a microorganism, it can also be obtained from a microorganism preservation institution. It should be noted that the numbers in parentheses represent CAS RN (registered trademark).

[1156] The combination of the component of the above group (a) and the compound of the present invention:

[1157] Abamectin + SX, Acephate + SX, Acequinocyl + SX, Acetamiprid + SX, Acetoprole + SX, Acrinathrin + SX, Acynonapyr + SX, Afidopyropen + SX, Afoxolaner + SX, Alanycarb + SX, Aldicarb + SX, Allethrin + SX, Alpha - Cypermethrin + SX, Alpha - Endosulfan + SX, Aluminium Phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos - ethyl + SX, Azinphos - methyl + SX, Azocyclotin + SX, Bark of Celastrus angulatus + SX, Bendiocarb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Benzoximate + SX, Benzpyrimoxan + SX, Beta - Cyfluthrin + SX, Beta - Cypermethrin + SX, Bifenazate + SX, Bifenthrin + SX, Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Borax + SX, Boric Acid + SX, Broflanilide + SX, Bromopropylate + SX, Buprofezin + SX, Butocarboxim + SX, Butoxycarboxim + SX, Cadusafos + SX, Calcium Phosphidephosphide)+SX, carbaryl+SX, carbofuran+SX, carbosulfan+SX, cartap hydrochloride+SX, cartap+SX, chinomethionat+SX, chlorantraniliprole+SX, chlordane+SX, chlorethoxyfos+SX, chlorfenapyr+SX, chlorfenvinphos+SX, chlorfluazuron+SX, chlormephos+SX, chloropicrin+SX, chlorpyrifos+SX, chlorpyrifos-methyl+SX, chromafenozide+SX, clofentezine+SX, clothianidin+SX, concanamycinA) +SX, coumaphos +SX, cryolite +SX, cyanophos +SX, cyantraniliprole +SX, cyclaniliprole +SX, cyclobutrifluram +SX, cycloprothrin +SX, cycloxaprid +SX, cyenopyrafen +SX, cyetpyrafen +SX, cyflumetofen +SX, cyfluthrin +SX, cyhalodiamide +SX, cyhalothrin +SX, cyhexatin +SX, cypermethrin +SX, cyphenothrin +SX, cyproflanilide +SX, cyromazine +SX, dazomet +SX, deltamethrin +SX, demeton-S-methyl +SX, diafenthiuron +SX, diazinon +SX, dichlorvos +SX, dicloromezotiaz +SX, dicofol +SX, dicrotophos +SX, diflovidazin +SX, diflubenzuron +SX, dimefluthrin +SX, dimethoate +SX, dimethylvinphos +SX, dimpropyridaz +SX, dinotefuran +SX, disodium octaborate +SX, disulfoton +SX, DNOC (2-methyl-4,6-dinitrophenol +SX, doramectin +SX, dried leaves of Dryopterisfilix-mas)+SX, emamectin-benzoate)+SX, empenthrin)+SX, endosulfan)+SX, EPN (O-ethyl O-(4-nitrophenyl)phenylphosphonothioate)+SX, epsilon-metofluthrin)+SX, epsilon-momfluorothrin+SX, esfenvalerate)+SX, ethiofencarb)+SX, ethion)+SX, ethiprole)+SX, ethoprophos)+SX, etofenprox)+SX, etoxazole)+SX, extract of Artemisia absinthium)+SX, extract of Azadirachta indica)+SX, extract of Cassia nigricans)+SX, extract of clitoria ternatea)+SX, extract of Symphytum officinale)+SX, extract of Chenopodium ambrosioides)+SX, extract of Tanacetum vulgare)+SX, extract of Urtica dioica)+SX, extract of Viscum album)+SX, famphur)+SX, fenamiphos)+SX, fenazaquin)+SX, fenbutatinoxide)+SX, fenitrothion+SX, fenmezoditiaz+SX, fenobucarb+SX, fenoxycarb+SX, fenpropathrin+SX, fenpyroximate+SX, fenthion+SX, fenvalerate+SX, fipronil+SX, flometoquin+SX, flonicamid+SX, fluacrypyrim+SX, fluazaindolizine+SX, fluazuron+SX, flubendiamide+SX, fluchlordiniliprole+SX, flucycloxuron+SX, flucythrinate+SX, fluensulfone+SX, flufenoprox+SX, flufenoxuron+SX, flufiprole+SX, flumethrin+SX, flupentiofenox+SX, flupyradifurone+SX, flupyrimin+SX, flupyroxystrobin+SX, fluralaner+SX, fluvalinate+SX, fluxametamide+SX, formetanate+SX, fosthiazate+SX, furamethrin+SX, furathiocarb+SX, gamma-cyhalothrin+SX, GS-omega / kappa HXTX-Hv1a peptide+SX, halfenprox+SX, halofenozide+SX, heptafluthrin+SX, heptenophos+SX, hexaflumuron+SX, hexythiazox+SX, potassium salt ofhop betaacid)+SX, hydramethylnon)+SX, hydroprene)+SX, imicyafos)+SX, imidacloprid)+SX, imidaclothiz)+SX, imiprothrin)+SX, indazapyroxamet)+SX, indoxacarb)+SX, isocycloseram+SX, isofenphos)+SX, isoprocarb)+SX, isopropyl-O-(methoxyaminothiophosphoryl)salicylate)+SX, isoxathion)+SX, ivermectin)+SX, kadethrin)+SX, kappa-tefluthrin)+SX, kappa-bifenthrin)+SX, kinoprene)+SX, lambda-cyhalothrin)+SX, ledprona+SX, lenoremycin)+SX, lepimectin)+SX, lime sulfur)+SX, lotilaner)+SX, lufenuron)+SX, machine oil)+SX, malathion)+SX, mecarbam)+SX, meperfluthrin)+SX, metaflumizone)+SX, metam)+SX, methamidophos)+SX, methidathion)+SX, methiocarb)+SX, methomyl)+SX, methoprene)+SX, methoxychlor)+SX, methoxyfenozide)+SX, methyl bromide)+SX, metofluthrin)+SX, metolcarb)+SX, metoxadiazone)+SX, mevinphos)+SX, milbemectin)+SX, milbemycinoxime)+SX, mivorilaner+SX, flubendiamide (modoflaner)+SX, momfluorothrin+SX, monocrotophos+SX, moxidectin+SX, naled+SX, nicofluprole+SX, nicotine+SX, nicotine-sulfate+SX, nitenpyram+SX, novaluron+SX, noviflumuron+SX, oil of the seeds of Chenopodium anthelminticum+SX, omethoate+SX, oxamyl+SX, oxazosulfyl+SX, oxydemeton-methyl+SX, parathion+SX, parathion-methyl+SX, permethrin+SX, phenothrin+SX, phenthoate+SX, phorate+SX, phosalone+SX, phosmet+SX, phosphamidon+SX, phosphine+SX, phoxim+SX, pirimicarb+SX, pirimiphos-methyl+SX, prallethrin+SX, profenofos+SX, profluthrin+SX, propargite+SX, propetamphos+SX, propoxur+SX, propylene glycol alginate (propyleneglycolalginate)+SX, prothiofos)+SX, pyflubumide+SX, pymetrozine)+SX, pyraclofos)+SX, pyrethrins)+SX, pyridaben)+SX, pyridalyl)+SX, pyridaphenthion)+SX, pyrifluquinazone)+SX, pyrimidifen)+SX, pyriminostrobin)+SX, pyriprole)+SX, pyriproxyfen)+SX, quinalphos)+SX, resmethrin)+SX, rotenone)+SX, ryanodine)+SX, sarolaner)+SX, selamectin)+SX, sigma-cypermethrin)+SX, silafluofen)+SX, sodium borate)+SX, sodium metaborate)+SX, spidoxamat+SX, spinetoram)+SX, spinosad)+SX, spirobudifen)+SX, spirodiclofen)+SX, spiromesifen)+SX, spiropidion)+SX, spirotetramat)+SX, sulfiflumin)+SX, sulfluramid)+SX, sulfotep)+SX, sulfoxaflor)+SX, sulfur)+SX, sulfurylfluoride)+SX, tartar emetic)+SX, tau-fluvalinate)+SX, tebufenozide)+SX, tebufenpyrad)+SX, tebupirimfos)+SX, teflubenzuron)+SX, tefluthrin)+SX, temephos)+SX, terbufos)+SX, terpene components extracted from Chenopodium ambrosioidesConstituents of the extract of Chenopodium ambrosioides near Ambrosioides)+SX, tetrachlorantraniliprole+SX, tetrachlorvinphos+SX, tetradifon+SX, tetramethrin+SX, tetramethylfluthrin+SX, tetraniliprole+SX, theta-cypermethrin+SX, thiacloprid+SX, thiamethoxam+SX, thiocyclam+SX, thiodicarb+SX, thiofanox+SX, thiometon+SX, thiosultap-disodium+SX, thiosultap-monosodium+SX, tigolaner+SX, tiorantraniliprole+SX, tioxazafen+SX, tolfenpyrad+SX, tralomethrin+SX, transfluthrin+SX, triazamate+SX, triazophos+SX, trichlorfon+SX, trifluenfuronate+SX, triflumezopyrim+SX, triflumuron+SX, trimethacarb+SX, tyclopyrazoflor+SX, umifoxolaner+SX, vamidothion+SX, wood extract of Quassia amara+SX, XMC (3,5-dimethylphenyl N-methylcarbamate, N-methylaminocarbonate 3,5-dimethylphenyl ester)+SX, xylylcarb+SX, zeta-cypermethrin+SX, zinc phosphide(zincphosphide) + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}inden-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methylsulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylthio)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methylsulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX, BT crop protein Cry1Fa + SX, BT cropprotein Cry1Fa)+SX, BT crop protein Cry1A.105)+SX, BT crop protein Cry2Ab)+SX, BT crop protein Vip3A)+SX, BT crop protein mCry3A)+SX, BT crop protein Cry3Ab)+SX, BT crop protein Cry3Bb)+SX, BT crop protein Cry34Ab1 / Cry35Ab1)+SX, Adoxophyes orana GV (granulovirus) strain BV-0001)+SX, Anticarsia gemmatalis MNPV (multiple nucleocapsid nucleopolyhedrovirus))+SX, Autographa californica MNPV)+SX, Cydia pomonella GV strain V15)+SX, Cydia pomonella GV strain V22)+SX, Cryptophlebia leucotreta GV)+SX, Dendrolimus punctatus cypovirus)+SX, Helicoverpa armigera NPV (nucleopolyhedrovirus) strain BV-0003)+SX, Helicoverpa zea NPV)+SX, Lymantria dispar NPV)+SX, Mamestra brassicae NPV)+SX, Mamestra configurata NPV)+SX, Neodiprion abietisNPV) + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer NPV + SX, Nosema locustae + SX, Orgyia pseudotsugata NPV + SX, Pieris rapae GV + SX, Plodia interpunctella GV + SX, Spodoptera exigua MNPV + SX, Spodoptera littoralis MNPV + SX, Spodoptera litura NPV + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX,CR-371)+SX, Bacillus thuringiensis subsp. aizawai strain ABTS-1857)+SX, Bacillus thuringiensis subsp. aizawai strain AM65-52)+SX, Bacillus thuringiensis subsp. aizawai strain GC-91)+SX, Bacillus thuringiensis subsp. aizawaistrain NB200)+SX, Bacillus thuringiensis subsp. aizawai Serotype strain H-7)+SX, Bacillus thuringiensis subsp. kurstaki strain ABTS351)+SX, Bacillus thuringiensis subsp. kurstaki strain BMP123)+SX, Bacillus thuringiensis subsp. kurstaki strain CCT1306)+SX, Bacillus thuringiensis subsp. kurstaki strain EG2348)+SX, Bacillus thuringiensis subsp. kurstaki strain EG7841)+SX, Bacillus thuringiensis subsp. kurstaki strain EVB113-19)+SX, Bacillus thuringiensis subsp. kurstaki strain F810)+SX, Bacillus thuringiensis subsp. kurstaki strain HD-1)+SXstrain HD-1)+SX, Bacillus thuringiensis subsp. Kurstaki strain PB54)+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11)+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12)+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176)+SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002)+SX, Bacillus thuringiensis subsp. morrisoni)+SX, Bacillus thuringiensis var. colmeri)+SX, Bacillus thuringiensis var. darmstadiensis strain 24-91)+SX, Bacillus thuringiensis var. dendrolimus)+SX, Bacillus thuringiensis var. galleriae)+SX, Bacillus thuringiensis var. israelensis strain BMP144)+SX, Bacillus thuringiensis var. israelensis serotype strain H-14)+SX, Bacillus thuringiensis var. japonensis strain buibui)+SX, Bacillus thuringiensis var. sandiego strain M-7)+SXM-7)+SX, Bacillus thuringiensis var.7216 +SX, Bacillus thuringiensis var. aegypti +SX, Bacillus thuringiensis var. T36 +SX, Beauveria bassiana strain ANT-03 +SX, Beauveria bassiana strain ATCC74040 +SX, Beauveria bassiana strain GHA +SX, Beauveria brongniartii +SX, Burkholderia rinojensis strain A396 +SX, Chromobacterium subtsugae strain PRAA4-1T +SX, Dactyllela ellipsospora +SX, Dectylaria thaumasia +SX, Hirsutella minnesotensis +SX, Hirsutella rhossiliensis +SX, Hirsutella thompsonii +SX, Lagenidium giganteum +SX, Lecanicillium lecanii strain KV01 +SX, Lecanicillium lecanii conidia of strain DAOM198499 +SX, Lecanicillium lecanii conidia of strain DAOM216596 +SX, Lecanicillium muscarium strain Ve6 +SX, Metarhizium anisopliae strain F52 +SX, Metarhizium anisopliae var. acridum +SX, Metarhizium anisopliae var. anisopliae var. minor BIPESCO5 / F52 strain (Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52) + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawa strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecanii strain NCIM1312 + SX, Wolbachia pipientis + SX.

[1158] Combination of the present component of group (b) with the compound of the present invention:

[1159] Acibenzolar-S-methyl + SX, Aldimorph + SX, Ametoctradin + SX, Aminopyrifen + SX, Amisulbrom + SX, Anilazine + SX, Azaconazole + SX, Azoxystrobin + SX, Basic copper sulfate + SX, Benalaxyl + SX, Benalaxyl-M + SX, Benodanil + SX, Benomyl + SX, Benthiavalicarb + SX, Benthiavalicarb-isopropyl + SX, Benzovindiflupyr + SX, Binapacryl + SX, Biphenyl + SX, Bitertanol + SX, Bixafen + SX, Blasticidin-S + SX, Bordeaux mixture + SX, Boscalid + SX, Bromothalonil + SX, Bromuconazole + SX, Bupirimate + SX, Captafol + SX, Captan + SX, Carbendazim + SX, Carboxin + SX, Carpropamid + SX, Chinomethionat + SX, Chitin + SX, Chloroinconazide + SX, Chloroneb + SX, Chlorothalonil + SX, Chlozolinate + SX, Colletochlorin B + SX, Copper(II)acetate + SX, Copper(II)hydroxide + SX, Copperoxychloride + SX, Copper(II)sulfate + SX, Coumoxystrobin + SX, Cyazofamid + SX, Cyflufenamid + SX,Cymoxanil + SX, Cyproconazole + SX, Cyprodinil + SX, Dichlobentiazox + SX, Dichlofluanid + SX, Diclocymet + SX, Diclomezine + SX, Dicloran + SX, Diethofencarb + SX, Difenoconazole + SX, Diflumetorim + SX, Dimethachlone + SX, Dimethirimol + SX, Dimethomorph + SX, Dimoxystrobin + SX, Diniconazole + SX, Diniconazole - M + SX, Dinocap + SX, Dipotassium hydrogenphosphite + SX, Dipymetitrone + SX, Dithianon + SX, Dodecylbenzenesulphonic acid bisethylenediamine copper(II)salt + SX, Dodemorph + SX, Dodine + SX, Edifenphos + SX, Enoxastrobin + SX, Epoxiconazole + SX, Etaconazole + SX, Ethaboxam + SX, Ethirimol + SX, Etridiazole + SX, Extract of Allium sativum, Extract of the cotyledons of lupine plantlets(“BLAD”), Extract of Equisetum arvense, Extract of Melaleuca alternifolia, Extract of Reynoutria sachalinensis, Extract of Tropaeolum majusFamoxadone + SX, Fenamidone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenbuconazole + SX, Fenfuram + SX, Fenhexamid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamid + SX, Fenpropidin + SX, Fenpropimorph + SX, Fenpyrazamine + SX, Fentin acetate, Fentinchloride, Fentin hydroxide, Ferbam, Ferimzone, Florylpicoxamid, Fluazinam, Flubeneteram, Fludioxonil, Flufenoxadiazam, Flufenoxystrobin, Fluindapyr, Flumetylsulforim, Flumorph, Fluopicolide, Fluopyram, Fluopimomide, Fluoroimide, Fluoxapiprolin, Fluoxastrobin, Fluoxytioconazole, Fluquinconazole, Flusilazole, Flusulfamide, Flutianil, Flutolanil, Flutriafol, Fluxapyroxad, Folpet, Fosetyl, Fosetyl-aluminium, Fuberidazole, Furalaxyl, Furametpyr, GuazatineHexaconazole + SX, Hymexazole + SX, Imazalil + SX, Imibenconazole + SX, Iminoctadine + SX, Iminoctadine triacetate + SX, Inpyrfluxam + SX, Iodocarb + SX, Ipconazole + SX, Ipfentrifluconazole + SX, Ipflufenoquin + SX, Iprobenfos + SX, Iprodione + SX, Iprovalicarb + SX, Isofetamid + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isotianil + SX, Kasugamycin + SX, Kresoxim-methyl + SX, Laminarin + SX, Leaves and bark of Quercus + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamid + SX, Maneb + SX, Mefentrifluconazole + SX, Mepanipyrim + SX, Mepronil + SX, Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Metarylpicoxamid + SX, Metconazole + SX, Methasulfocarb + SX, Metiram + SX, Metominostrobin + SX, Metrafenone + SX, Metyltetraprole + SX, Myclobutanil + SX, Naftifine + SX, Nuarimol + SX, Octhilinone + SX, Ofurace + SX, Orysastrobin + SX, Oxadixyl + SX,Oxathiapiprolin + SX, Oxine - copper + SX, Oxolinic acid + SX, Oxpoconazole + SX, Oxpoconazole fumarate + SX, Oxycarboxin + SX, Oxytetracycline + SX, Pefurazoate + SX, Penconazole + SX, Pencycuron + SX, Penflufen + SX, Penthiopyrad + SX, Phenamacril + SX, Phosphorous acid + SX, Phthalide + SX, Picarbutrazox + SX, Picoxystrobin + SX, Piperalin + SX, Polyoxins + SX, Potassium hydrogencarbonate + SX, Potassium dihydrogenphosphite + SX, Probenazole + SX, Prochloraz + SX, Procymidone + SX, Propamidine + SX, Propamocarb + SX, Propiconazole + SX, Propineb + SX, Proquinazid + SX, Prothiocarb + SX, Prothioconazole + SX, Pydiflumetofen + SX, Pyraclostrobin + SX, Pyrametostrobin + SX, Pyraoxystrobin + SX, Pyrapropoyne + SX, Pyraziflumid + SX, Pyrazophos + SX, Pyribencarb + SX, Pyributicarb + SX, Pyridachlometyl + SX, Pyrifenox + SX, Pyrimethanil + SX, Pyrimorph + SX,Pyriofenone + SX, Pyrisoxazole + SX, Pyroquilon + SX, Quillaja extract + SX, Quinconazole + SX, Quinofumelin + SX, Quinoxyfen + SX, Quintozene + SX, Saponins of Chenopodium quinoa + SX, Seboctylamine + SX, Sedaxane + SX, Silthiofam + SX, Simeconazole + SX, Sodium hydrogencarbonate + SX, Spiroxamine + SX, Streptomycin + SX, Sulfur + SX, Tebuconazole + SX, Tebufloquin + SX, Teclofthalam + SX, Tecnazene + SX, Terbinafine + SX, Tetraconazole + SX, Thiabendazole + SX, Thifluzamide + SX, Thiophanate + SX, Thiophanate-methyl + SX, Thiram + SX, Thymol + SX, Tiadinil + SX, Tolclofos-methyl + SX, Tolfenpyrad + SX, Tolprocarb + SX, Tolylfluanid + SX, Triadimefon + SX, Triadimenol + SX, Triazoxide + SX, Triclopyricarb + SX, Tricyclazole + SX, Tridemorph + SX, Trifloxystrobin + SX, Triflumizole + SX, Triforine + SX, Triticonazole + SX, Validamycin + SX, Valifenalate + SX,Vinclozolin + SX, Yellow mustard powder + SX, Zinc thiazole + SX, Zineb + SX, Ziram + SX, Zoxamide + SX, N’-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (1202781-91-6) + SX, N’-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidine (929908-57-6) + SX, N’-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine (1052688-31-9) + SX, N’-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylformamidine (2055589-28-9) + SX, N’-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine (2055756-21-1) + SX, N’-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformamidine (2062599-39-5) + SX, N’-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylformamidine (2101814-55-3) + SX, N’-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidine (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, (2Z)-Ethyl 3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX,(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R,2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S,2R,5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentane-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX,2-(Difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(Difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethylsulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SXN-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(4-bromo-7-fluoroindol-1-yl)but-2-yl ester + SX, N-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromoindol-1-yl)but-2-yl ester + SX, N-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindol-1-yl)but-2-yl ester + SX, N-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester + SX, N-{[3-(Acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester + SX, N-[(3-Hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-[(3-Acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate) + SX, N-{[3-(Acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate) + SX, N-({4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-Allyl-N-({4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-Allyl-N-({4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX,3,3,3-Trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N’-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N’-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N’-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylic acid ethyl ester + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SXN-Methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX2-[Cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[Cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[Acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-Methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-Methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-Difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(Oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(Oxolane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(Oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX3-[3-(3-Cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-Cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-Fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-Fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-Fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-Methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-Fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SXMethyl ((5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl)methyl)carbamate + SX, Methyl ((5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl)methyl)carbamate + SX, Methyl ((5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl)methyl)carbamate + SX, Methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyacrylate + SX, Methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyacrylate + SX, Methyl (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxyacrylate + SX, 1-(4,5-dimethyl-1H-benzoimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzoimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, Methyl (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]acrylate + SX, Agrobacterium radiobactor strain K1026, Agrobacterium radiobactor strain K84, Bacillus amyloliquefaciens strain PTA-4838 (Aveo (trademark) EZNematicide), Bacillus amyloliquefaciens strain AT332, Bacillus amyloliquefaciens strain B3, Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain DB101Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SXBacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SXBurkholderia cepacia type Wisconsin strain M54 + SX, biocontrol yeast Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, Cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SXPseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa PF-A22UL strain + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SXTrichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SXTrichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, Trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride, Variovorax paradoxus strain CGF4526 + SX, Harpin protein.,

[1160] Combination of the component of the above group (c) with the compound of the present invention:

[1161] 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, cholinechloride)+SX, cloprop)+SX, cyanamide)+SX, cyclanilide)+SX, daminozide)+SX, decan-1-ol)+SX, dichlorprop)+SX, dikegulac)+SX, dimethipin)+SX, diquat)+SX, ethephon)+SX, ethychlozate)+SX, flumetralin)+SX, flurprimidol)+SX, forchlorfenuron)+SX, formononetin)+SX, Gibberellin A)+SX, GibberellinA3)+SX, inabenfide)+SX, Kinetin)+SX, lipochitooligosaccharide)SP104+SX, maleic hydrazide)+SX, mefluidide)+SX, mepiquat-chloride)+SX, oxidizedglutathione)+SX, paclobutrazol)+SX, pendimethalin)+SX, prohexadione-calcium)+SX, prohydrojasmon)+SX, pyraflufen-ethyl)+SX, sintofen)+SX, sodium 1-naphthaleneacetate)+SX, sodium cyanate)+SX, thidiazuron)+SX, triapenthenol)+SX, tribufos)+SX, trinexapac-ethyl)+SX, uniconazole-P)+SX, 2-(naphthalen-1-yl)acetamide)+SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid+SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate+SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol+SX, Claroideoglomusetunicatum)+SX, Claroideoglomus claroideum)+SX, Funneliformis mosseae)+SX, Gigaspora margarita)+SX, Gigaspora rosea)+SX, Glomus aggregatum)+SX, Glomus deserticola)+SX, Glomus monosporum)+SX, Paraglomus brasillianum)+SX, Rhizophagus clarus)+SX, Rhizophagus intraradices strain RTI-801+SX, Rhizophagus irregularis strain DAOM 197198+SX, Azorhizobium caulinodans)+SX, Azospirillum amazonense)+SX, Azospirillum brasilense strain XOH+SX, Azospirillum brasilense Ab-V5 strain+SX, Azospirillum brasilense Ab-V6 strain+SX, Azospirillum caulinodans+SX, Azospirillum halopraeferens)+SX, Azospirillum irakense)+SX, Azospirillum lipoferum)+SX, Bradyrhizobium elkanii strain SEMIA 587+SX, Bradyrhizobium elkanii strain SEMIA 5019+SX, Bradyrhizobium japonicum strain TA-11+SX, Bradyrhizobium japonicum strain USDA 110+SX, Bradyrhizobium liaoningense)+SX, Bradyrhizobium lupini)+SX, Delftia acidovorans strain RAY209+SX, Mesorhizobium ciceri)+SX, Mesorhizobium huakuiiHuakii)+SX, Mesorhizobium loti)+SX, Rhizobium etli)+SX, Rhizobium galegae)+SX, Rhizobium leguminosarum bv. Phaseoli)+SX, Rhizobium leguminosarum bv. Trifolii)+SX, Rhizobium leguminosarum bv. Viciae)+SX, Rhizobium trifolii)+SX, Rhizobium tropici)+SX, Sinorhizobium fredii)+SX, Sinorhizobium meliloti)+SX, Zucchini Yellow Mosaik Virus weak strain)+SX.

[1162] The combination of the present component of group (d) and the compound of the present invention:

[1163] Anthraquinone)+SX, Deet)+SX, Icaridin)+SX.

[1164] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc. in terms of weight ratio (compound of the present invention: present component).

[1165] The compound of the present invention can control harmful arthropods such as harmful insects and harmful mites, harmful nematodes and harmful mollusks. Examples of harmful arthropods, harmful nematodes and harmful mollusks include the following animals.

[1166] Hemiptera: Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus, Stenocranus pacificus, etc.; Cicadellidae such as Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, Empoasca fabae, Dalbulus maidis, Cofana spectra, Amrasca biguttula biguttula, etc.; Aphrophoridae such as Philaenus spumarius; Cercopidae such as Mahanarva posticata, Mahanarva fimbriolata, etc.Aphididae such as Aphisfabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Myzus persicae, Brachycaudus helichrysi, Brevicoryne brassicae, Dysaphis plantaginea, Lipaphis erysimi, Macrosiphum euphorbiae, Aulacorthum solani, Nasonovia ribisnigri, Rhopalosiphumpadi, Rhopalosiphum maidis, Toxoptera citricida, Hyalopterus pruni, Melanaphis sacchari, Tetraneuranigriabdominalis, Ceratovacuna lanigera, Eriosomalanigerum, Sitobion avenae, etc.; Phylloxeridae such as Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, Phylloxera russelae, etc.; Adelgidae such as Adelges tsugae, Adelges piceae, Aphrastasia pectinatae, etc.;Pentatomidae such as Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, Nezara viridula, Euschistus heros, Piezodorus guildinii, Oebalus pugnax, Dichelops melacanthus, Piezodorus hybneri, etc.; Cydnidae such as Scaptocoris castanea, etc.; Alydidae such as Riptortus clavatus, Leptocorisa chinensis, Leptocorisa acuta, etc.; Coreidae such as Cletus punctiger, Leptoglossus australis, etc.; Lygaeidae such as Cavelerius saccharivorus, Togohemipterus, Blissus leucopterus, etc.; Miridae such as Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, Lygus lineolaris, etc.; Aleyrodidae such as Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, Pealius euryae, etc.Scale insects in the family Diaspididae such as Abgrallaspis cyanophylli, Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, Unaspis citri, etc.; scale insects in the family Coccidae such as Ceroplastes rubens, etc.; scale insects in the family Margarodidae such as Icerya purchasi, Icerya seychellarum, etc.; scale insects in the family Pseudococcidae such as Phenacoccus solani, Phenacoccus solenopsis, Planococcus kraunhiae, Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, Brevennia rehi, etc.; psyllids in the family Psyllidae such as Diaphorina citri, Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, Cacopsylla pyricola, etc.; lace bugs in the family Tingidae such as Corythucha ciliata, Corythucha marmorata, Stephanitis nashi, Stephanitis pyrioides, etc.; bed bugs in the family Cimicidae such as Cimex lectularius, Cimex hemipterus, etc.; cicadas in the family Cicadidae such as Quesada gigas, etc.Triatomine bugs such as Triatoma infestans, Triatoma rubrofasciata, Triatoma dimidiata, Rhodnius prolixus, etc. (Reduviidae);

[1167] Lepidoptera: Crambidae such as Chilo suppressalis, Chilopolychrysus, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmiapatnalis, Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, Ostrinia nubilalis, Hellula undalis, Herpetogramma luctuosale, Parapediasiateterrellus, Nymphula depunctalis, Diatraea saccharalis, Leucinodes orbonalis, etc.; Pyralidae such as Elasmopalpus lignosellus, Plodia interpunctella, Euzophera batangensis, Cadra cautella, etc.Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Plusia festucae, Chrysodeixis includens, Trichoplusia spp., Heliothis virescens and other Heliothis spp., Helicoverpa armigera, Helicoverpa zea and other Helicoverpa spp., Anticarsia gemmatalis, Alabama argillacea, Hydraecia immanis and other Noctuidae; Pieris rapae and other Pieridae;Tortricidae such as Grapholita molesta, Grapholita dimorpha, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Bean Shoot Borer (Epinotia aporema), Citripestis sagittiferella, Lobesia botrana, etc.; Gracillariidae such as Caloptilia theivora, Phyllonorycter ringoniella, etc.; Carposinidae such as Carposina sasakii, etc.; Lyonetiidae such as Leucoptera coffeella, Lyonetia clerkella, Lyonetia prunifoliella, etc.; Lymantriidae such as Lymantria dispar of Lymantria spp., Euproctis pseudoconspersa of Euproctis spp., etc.; Plutellidae such as Plutella xylostella, etc.; Gelechiidae such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, Tuta absoluta, etc.; Arctiidae such as Hyphantria cunea, etc.; Castniidae such as Telchin licus, etc.Cossidae such as Cossus insularis; Geometridae such as Ascotis selenaria; Limacodidae such as Parasalepida; Stathmopodidae such as Stathmopoda masinissa; Sphingidae such as Acherontia lachesis; Sesiidae such as Nokonaferalis, Synanthedon hector, Synanthedon tenuis; Hesperiidae such as Parnara guttata; Tineidae such as Tinea translucens, Tineola bisselliella.

[1168] Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, Scirtothrips perseae; Phlaeothripidae such as Haplothrips aculeatus.

[1169] Diptera: Anthomyiidae such as Delia platura, Delia antiqua, Pegomya cunicularia, etc.; Ulidiidae such as Tetanops myopaeformis, etc.; Agromyzidae such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, Chromatomyia horticola, etc.; Chloropidae such as Chlorops oryzae, etc.; Tephritidae such as Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, Rhacochlaena japonica, etc.; Ephydridae such as Hydrellia griseola, Hydrellia philippina, Hydrellia sasakii, etc.; Drosophilidae such as Drosophila suzukii, Drosophila melanogaster, etc.; Phoridae such as Megaselia spiracularis, etc.; Psychodidae such as Clogmia albipunctata, etc.; Sciaridae such as Bradysia difformis, Bradysia odoriphaga, etc.; Cecidomyiidae such as Mayetiola destructor, Orseolia oryzae, etc.; Diopsidae such as Diopsis macrophthalma, etc.Glossinidae such as Glossina palpalis, Glossina morsitans; Simuliidae such as Simulium japonicum, Simulium damnosum; Phlebotominae; Tipulidae such as Tipula aino, Tipula oleracea, Tipula paludosa; Culicidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus; Simuliidae such as Prosimulium yezoensis, Simulium ornatum; Tabanidae such as Tabanus trigonus; Muscidae such as Musca domestica, Muscina stabulans, Stomoxys calcitrans, Haematobia irritans; Calliphoridae; Sarcophagidae;Chironomidae such as Chironomus plumosus, Chironomus yoshimatsui, Glyptotendipes tokunagai, etc.; Fannidae.

[1170] Coleoptera: Diabrotica spp. (e.g., Diabrotica virgifera virgifera, Diabrotica undecimpunctata howardi, Diabrotica barberi, Diabrotica virgifera zeae, Diabrotica balteata, Cucurbit Beetle (Diabrotica speciosa), etc.), Cerotoma trifurcata, Oulema melanopus, Aulacophora femoralis, Phyllotreta striolata, Phyllotreta cruciferae, Phyllotreta pusilla, Psylliodes chrysocephala, Psylliodes punctulata, Leptinotarsa decemlineata, Oulema oryzae, Colaspis brunnea, Chaetocnema pulicaria, Chaetocnema confinis, Epitrix cucumeris, Dicladispa armigera, Myochrous denticollis, Laccoptera quadrimaculata, Epitrix hirtipennis, Phaedon brassicae, Medythia nigrobilineata, etc. (Chrysomelidae); Seedcorn beetle (Stenolophus lecontei), Clivina impressifrons, etc. (Carabidae);Scarabaeidae such as Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica, Heptophyllapicea, Rhizotrogus majalis, Tomarus gibbosus, Holotrichia spp., Phyllophaga crinita and other Phyllophaga spp., Diloboderus abderus and other Diloboderus spp.; Anthriibidae such as Araecerus coffeae; Aponidae such as Cylas formicarius; Bruchidae such as Zabrotes subfasciatus; Scolytidae such as Tomicus piniperda, Hypothenemus hampei; Curculionidae such as Euscepes postfasciatus, Hypera postica, Sitophilus zeamais, Sitophilus oryzae, Sitophilus granarius, Echinocnemus squameus, Lissorhoptrus oryzophilus, Rhabdoscelus lineaticollis, Anthonomus grandis, Sphenophorus venatus, Sphenophorus callosus, Sternechus subsignatus, Sphenophorus levis, Scepticus griseus, Scepticus uniformis, Aracanthus mourei and other Aracanthus spp., Eutinobothrus brasiliensis and other Curculionidae;Tenebrionidae such as Tribolium castaneum, Tribolium confusum, Alphitobius diaperinus, etc.; Coccinellidae such as Epilachna vigintioctopunctata, etc.; Bostrychidae such as Lyctus brunneus, Rhizopertha dominica, etc.; Ptinidae; Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus, Aromia bungii, etc.; Elateridae such as Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius spp., Aeolus spp., etc.; Staphylinidae such as Paederus fuscipes, etc.; Dermestidae such as Anthrenus verbasci, Dermestes maculates, Trogoderma granarium, etc.; Anobiidae such as Lasioderma serricorne, Stegobium paniceum, etc.; Laemophloeidae such as Cryptolestes ferrugineus, etc.; Silvanidae such as Oryzaephilus surinamensis, etc.; Nitidulidae such as Brassicogethes aeneus, etc.

[1171] Orthoptera: Acrididae such as Locusta migratoria, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacris septemfasciata, Locustana pardalina, Anacridium melanorhodon, Calliptamus italicus, Melanoplus differentialis, Melanoplus bivittatus, Melanoplus sanguinipes, Melanoplus femurrubrum, Camnula pellucida, Schistocerca gregaria, Gastrimargus musicus (Yellow-winged locust), Austracris guttulosa (Spur-throated locust), Oxya yezoensis, Oxya japonica, Patanga succincta, etc.; Gryllotalpidae such as Gryllotalpa orientalis; Gryllidae such as Acheta domestica, Teleogryllus emma; Tettigoniidae such as Anabrus simplex.

[1172] Hymenoptera: Tenthredinidae such as Athalia rosae, Athalia japonica; Solenopsis spp. such as Solenopsis invicta, Solenopsis geminata, Atta spp. such as Brown leaf-cutting ant (Attacapiguara), Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomorium pharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes and other Camponotus spp., Pogonomyrmex occidentalis and other Pogonomyrmex spp., Wasmania auropunctata and other Wasmania spp., Anoplolepis gracilipes and other Formicidae; Vespidae such as Vespa mandarinia, Vespa simillima, Vespa analis, Vespa velutina, Polistes jokahamae; Siricidae such as Urocerus gigas; Bethylidae.

[1173] Order Blattodea: Ectobiidae such as Blattella germanica; Blattidae such as Periplaneta fuliginosa, Periplaneta americana, Periplaneta australasiae, Periplaneta brunnea, Blatta orientalis; Termitidae such as Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, Cornitermes cumulans.

[1174] Order Siphonaptera: Pulicidae such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Echidnophaga gallinacea; Hectopsyllidae such as Tunga penetrans; Ceratophyllidae such as Nosopsyllus fasciatus.

[1175] Psocodea: Pediculidae such as Pediculus humanus capitis; Pthiridae such as Pthirus pubis; Haematopinidae such as Haematopinus eurysternus and Haematopinus suis; Linognathidae such as Linognathus vituli, Linognathus ovillus, and Solenopotes capillatus; Bovicoliidae such as Bovicola bovis, Bovicola ovis, Bovicola breviceps, Damalinia forficula, and Werneckiella spp.; Trichodectidae such as Trichodectes canis and Felicola subrostratus; Menoponidae such as Menopon gallinae, Menacanthus stramineus, and Trinoton spp.; Trimenoponidae such as Cummingsia spp.; Trogiidae such as Trogium pulsatorium; Liposcelidae or Liposcelididae such as Liposcelis corrodens, Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelis entomophila.

[1176] Thysanura: Lepismatidae such as Ctenolepisma villosa and Lepisma saccharina.

[1177] Order Acari: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp.; Eriophyidae such as Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus schlechtendali, Aceria diospyri, Aceria tosichella, Shevtchenkella sp.; Tarsonemidae such as Polyphagotarsonemus latus; Tenuipalpidae such as Brevipalpus phoenicis; Tuckerellidae;Hard ticks of the family Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Dermacentor andersoni, Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus decoloratus, etc.; soft ticks of the family Argasidae such as Argas persicus, Ornithodoros hermsi, Ornithodoros turicata, etc.; flour mites of the family Acaridae such as Tyrophagus putrescentiae, Tyrophagus similis, etc.; house dust mites of the family Pyroglyphidae such as Dermatophagoides farinae, Dermatophagoides pteronyssinus, etc.; predatory mites of the family Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, Cheyletiella yasguri, etc.Psoroptidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, Chorioptes spp.; Sarcoptidae such as Notoedres cati, Notoedres muris, Sarcoptes scabiei; Listrophoridae such as Listrophorus gibbus; Dermanyssidae such as Dermanyssus gallinae; Macronyssidae such as Ornithonyssus sylviarum, Ornithonyssus bacoti; Varroidae such as Varroa jacobsoni; Demodicidae such as Demodex canis, Demodex cati; Trombiculidae such as Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium scutellare.

[1178] Araneae: Eutichuridae such as Cheiracanthium japonicum; Theridiidae such as Latrodectus hasseltii.

[1179] Polydesmida: Paradoxosomatidae such as Oxidus gracilis, Nedyopus tambanus.

[1180] Isopoda: Armadillidiidae such as Armadillidium vulgare.

[1181] Chilopoda: Scutigeridae such as Thereuonema hilgendorfi; Scolopendridae such as Scolopendra subspinipes; Ethopolyidae such as Bothropolys rugosus.

[1182] Gastropoda: Limacidae such as Limax marginatus, Limax flavus; Philomycidae such as Meghimatium bilineatum; Ampullariidae such as Pomacea canaliculata; Lymnaeidae such as Austropeplea ollula.

[1183] Nematoda: Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchidae such as Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus neglectus, Radopholus similis; Heteroderidae such as Meloidogyne javanica, Meloidogyne incognita, guava root - knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, Heterodera glycines, Globodera rostochiensis, Globodera pallida, Meloidogyne chitwoodi; Hoplolaimidae such as Rotylenchulus reniformis; Anguinidae such as Nothotylenchus acris, Ditylenchus dipsaci; Tylenchulidae such as Tylenchulus semipenetrans; Longidoridae such as Xiphinema index; Trichodoridae; Parasitaphelenchidae such as Bursaphelenchus xylophilus.

[1184] Harmful arthropods such as harmful insects and harmful mites, harmful mollusks and harmful nematodes can also be harmful insects, harmful mites and other harmful arthropods, harmful mollusks and harmful nematodes with reduced susceptibility to pesticides, acaricides, molluscicides or nematicides, or with strong drug resistance.

[1185] As the method for controlling harmful arthropods of the present invention, it can be implemented by directly applying an effective amount of the compound or composition A of the present invention to harmful arthropods and / or to the habitats of harmful arthropods (plants, soil, indoors of houses, animals, etc.). As the method for controlling harmful arthropods of the present invention, for example, foliar treatment, soil treatment, root treatment, spraying treatment, fumigation treatment, water surface treatment, and seed treatment can be cited.

[1186] For the compound or composition A of the present invention, usually an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc. and a surfactant, etc. are mixed, and auxiliary agents for formulation such as a binder, a dispersant, a stabilizer, etc. are added as needed, and formulated into an aqueous suspension formulation, an oily suspension formulation, an oil formulation, an emulsion, an emulsion formulation, a microemulsion formulation, a microcapsule formulation, a wettable powder, a water-dispersible granule, a powder, a granule, a tablet, an aerosol, a resin formulation, etc. for use. It is not limited to these formulations, and it can be formulated into the dosage forms described in Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers - 271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications (Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers - 271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications), 2016, ISSN: 0259 - 2517 for use.

[1187] In these formulations, usually 0.0001~99% of the compound or composition A of the present invention is contained by weight.

[1188] As the solid carrier, for example, clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, palygorskite, silica white, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powders and granular substances of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.) can be cited.

[1189] As the liquid carrier, examples include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylene ethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[1190] As the gaseous carrier, examples include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[1191] As the surfactant, examples include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkyl aryl sulfonates, alkyl sulfates, etc.).

[1192] As other adjuvants for the preparation, binders, dispersants, colorants, stabilizers, etc. can be cited. Specifically, examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, and dibutylhydroxytoluene.

[1193] In addition, as the component for enhancing or assisting the efficacy of the compound of the present invention, adjuvants can be used. Specifically, examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark), etc.

[1194] In the present invention, as the plant, the whole plant, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative propagation organs, and seedlings can be cited.

[1195] Vegetative propagation organs refer to: among the roots, stems, leaves, etc. of plants, those parts that have the ability to grow when separated from the main body and placed in the soil. Examples of vegetative propagation organs include tuberous root, creeping root, bulb, corm (or solid bulb), tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cutting. It should be noted that stolons are sometimes also called runners, and propagules are also called bulbils, which are divided into broad buds and bulbils. Vine cuttings refer to the slender shoots (collective term for leaves and stems, shoots without roots) of sweet potatoes, Dioscorea japonica, etc. Bulbs, corms, tubers, rhizomes, cane cuttings, rhizophores, or tuberous roots are also collectively called bulbs. The cultivation of potatoes starts by planting tubers in the soil, but the tubers used are usually called seed potatoes.

[1196] As a method of applying an effective amount of the compound or composition A of the present invention to the soil to control harmful arthropods, for example, there is a method of applying an effective amount of the compound or composition A of the present invention to the soil before or after transplanting plants. More specifically, for example, hole treatment (hole spraying, hole soil mixing), root treatment (root spraying, root soil mixing, root irrigation, late-stage root treatment during the seedling raising period), furrow treatment (furrow spraying, furrow soil mixing), ridge furrow treatment (ridge furrow spraying, ridge furrow soil mixing, ridge furrow spraying during the growth period), furrow treatment at sowing (furrow spraying at sowing, furrow soil mixing at sowing), overall treatment (whole soil spraying, whole soil mixing), side treatment of ridge cultivation, water surface treatment (water surface application, water surface application after water storage), other soil spraying treatments (granule foliar spraying during the growth period, spraying under the canopy or around the main trunk, soil surface spraying, soil surface mixing, hole spraying, surface spraying of the ridge part, inter-plant spraying), other irrigation treatments (soil irrigation, seedling raising irrigation, liquid injection treatment, plant base irrigation, drip irrigation of liquid medicine, chemical solution irrigation), seedling box treatment (seedling box spraying, seedling box irrigation, accumulation of liquid medicine in the seedling box), seedling tray treatment (seedling tray spraying, seedling tray irrigation, accumulation of liquid medicine in the seedling tray), seedbed treatment (seedbed spraying, seedbed irrigation, seedbed spraying in the rice nursery, seedling immersion), bed soil mixing treatment (bed soil mixing, bed soil mixing before sowing, spraying before covering soil at sowing, spraying after covering soil at sowing, covering soil mixing), and other treatments (cultivated soil mixing, turning in, topsoil mixing, soil mixing at the rain dripping part, planting position treatment, granule calyx spraying, paste fertilizer mixing).

[1197] As seed treatment, for example, the treatment of seeds or vegetative propagation organs with the compound or composition A of the present invention can be mentioned. Specifically, for example: spraying treatment in which a suspension of the compound or composition A of the present invention is atomized and sprayed onto the surface of seeds or vegetative propagation organs; coating treatment in which the compound or composition A of the present invention is coated on seeds or vegetative propagation organs; dipping treatment in which seeds or vegetative propagation organs are dipped in a liquid medicine of the compound or composition A of the present invention for a certain period of time; a method of coating seeds or vegetative propagation organs with a carrier containing the compound or composition A of the present invention (coating treatment, pellet coating treatment, etc.). As the above-mentioned vegetative propagation organs, seed potatoes can be particularly mentioned.

[1198] When treating seeds or vegetative propagation organs with composition A, composition A can be made into a single preparation for treating seeds or vegetative propagation organs, or composition A can be made into different multiple preparations and used to treat seeds or vegetative propagation organs in several times. As a method of making composition A into different multiple preparations and treating in several times, for example: treating with a preparation containing only the compound of the present invention as an active ingredient, air-drying the seeds or vegetative propagation organs, and then treating with a preparation containing this ingredient; and treating with a preparation containing the compound of the present invention and this ingredient as active ingredients, air-drying the seeds or vegetative propagation organs, and then treating with a preparation containing this ingredient other than the ingredient that has been treated.

[1199] The seeds or vegetative propagation organs holding the compound or composition A of the present invention in the present invention refer to: seeds or vegetative propagation organs in a state where the compound or composition A of the present invention is attached to the surface of the seeds or vegetative propagation organs. For the above-mentioned seeds or vegetative propagation organs holding the compound or composition A of the present invention, materials other than the compound or composition A of the present invention can be attached before and after attaching the compound or composition A of the present invention to the seeds or vegetative propagation organs.

[1200] In addition, when composition A forms a layer and adheres to the surface of seeds or vegetative propagation organs, the layer is formed of one layer or multiple layers. In addition, when formed of multiple layers, each layer is a layer containing one or more active ingredients, or is formed of a layer containing one or more active ingredients and a layer not containing active ingredients.

[1201] The seeds or vegetative propagation organs holding the compound or composition A of the present invention can be obtained, for example, by the following method: applying a preparation containing the compound or composition A of the present invention to seeds or vegetative propagation organs by using the aforementioned seed treatment method.

[1202] When the compound or composition A of the present invention is used for controlling harmful arthropods in the agricultural field, the application rate is usually 1 to 10,000 g in terms of the amount of the compound of the present invention per 10,000 m 2 . When treating seeds or vegetative propagation organs, the amount of the compound of the present invention is usually applied in the range of 0.001 to 100 g relative to 1 Kg of seeds or vegetative propagation organs. When the compound or composition A of the present invention is formulated into an emulsion, wettable powder, suspension agent, etc., it is usually diluted with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm and applied, and granules, powders, etc. are usually applied directly.

[1203] In addition, the compound or composition A of the present invention can also be treated by methods such as winding resin preparations processed into sheets or lines around crops, stretching them near crops, or laying them on the root soil.

[1204] When the compound or composition A of the present invention is used for controlling harmful arthropods inhabiting in houses, for its application rate, when treating on the surface, in terms of the amount of the compound of the present invention per 1 m 2 of the treatment area, it is usually 0.01 to 1000 mg, and when treating in the space, in terms of the amount of the compound of the present invention per 1 m 3 of the treatment space, it is usually 0.01 to 500 mg. When the compound or composition A of the present invention is formulated into an emulsion, wettable powder, suspension agent, etc., it is usually diluted with water so that the active ingredient concentration becomes 0.1 to 10,000 ppm and applied, and oil agents, aerosol agents, fumigants, bait agents, etc. are applied directly.

[1205] When the compound or composition A of the present invention is used for controlling external parasites of livestock such as cattle, horses, pigs, sheep, goats, chickens, and small animals such as dogs, cats, rats, and mice, it can be used for animals by methods known in veterinary medicine. As a specific method of use, for the purpose of systemic inhibition, it is administered by, for example, tablets, mixing in feed, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and for the purpose of non-systemic inhibition, it is used by methods such as spraying an oil agent or aqueous liquid agent, pouring treatment or drip treatment, washing the animal with a shampoo preparation, or making a resin preparation into a collar, ear tag and having the animal wear it. The amount of the compound or composition A of the present invention when administered to an animal is usually in the range of 0.1 to 1000 mg relative to 1 kg of the animal's body weight.

[1206] The compound or composition A of the present invention can be used as a controlling agent for harmful arthropods in agricultural cultivated lands such as dry fields, paddy fields, lawns, and orchards. As plants, for example, the following plants can be cited.

[1207] Maize (dent corn, flint corn, soft corn, pop corn, waxy corn, sweet corn, non-sweet corn), rice (long grain rice, short grain rice, medium grain rice, japonica rice, tropical japonica rice, indica rice, javanica rice, paddy rice, upland rice, floating rice, direct seeding, transplantation, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, their respective winter wheat types, spring wheat types), barley (two-row barley (= brewing barley), six-row barley, hull-less barley, sticky barley, their respective winter barley types, spring barley types), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland cotton, pima cotton), soybean (mature seed harvest variety, edamame variety, green manure variety, their respective indeterminate growth type, determinate growth type, semi-determinate growth type), peanut, buckwheat, sugar beet (for sugar production, for feed, root vegetable, leaf vegetable, for fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (for oil extraction, for food, for ornamental use), sugarcane, tobacco, tea plant, mulberry, solanaceous vegetables (eggplant, tomato, green pepper, chili pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, spring chrysanthemum, artichoke, lettuce, etc.), liliaceous vegetables (scallion, onion, garlic, asparagus, etc.), umbelliferous vegetables (carrot, parsley, celery, parsnip, etc.), chenopodiaceous vegetables (spinach, chard, etc.), labiatae vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, Japanese yam, taro, pome fruits (apple, European pear, Japanese pear, white pear, Chinese quince, quince, etc.), stone fruits (peach, plum, nectarine, ume, cherry, apricot, prune, etc.), citrus fruits (Satsuma mandarin, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, fig, olive, loquat, banana, coffee, date palm, coconut, ornamental plants, forest plants, turf grasses, forage grasses.

[1208] The above-mentioned plants only need to be commonly cultivated varieties, without any particular limitation. The above-mentioned plants also include plants that can be produced by natural mating, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. As genetically modified crops, for example, plants that have been given tolerance to HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, herbicides such as bromoxynil or dicamba; plants that can synthesize selective toxins known in Bacillus species such as Bacillus thuringiensis; plants that can confer specific insecticidal activity by synthesizing gene fragments partially identical to endogenous genes from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insects.

[1209] Examples

[1210] Hereinafter, the present invention will be described in more detail by means of production examples, formulation examples, test examples, etc., but the present invention is not limited only to these examples.

[1211] In this specification, Me represents methyl, Et represents ethyl, Pr represents propyl, i-Pr represents isopropyl, Bu represents butyl, t-Bu represents tert-butyl, Hex represents hexyl, c-Pr represents cyclopropyl, c-Bu represents cyclobutyl, Ph represents phenyl, Boc represents tert-butoxycarbonyl, Bn represents benzyl, Py2 represents 2-pyridyl, Py3 represents 3-pyridyl, and Py4 represents 4-pyridyl. When c-Pr, Ph, Py2, Py3, and Py4 are substituted with substituents, the substituents and the substitution positions are described together before the symbol. For example, 1-CN-c-Pr represents 1-cyanocyclopropyl, 3,4-F2-Ph represents 3,4-difluorophenyl, and 4-CF3-Py2 represents 4-(trifluoromethyl)-2-pyridyl.

[1212] First, production examples of the compounds of the present invention and their production intermediates are shown.

[1213] When measuring the physical property values of the compounds by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] + or [M-H] - and the retention time (hereinafter referred to as RT) are recorded. The conditions for liquid chromatography (hereinafter referred to as LC) are as described below.

[1214] [LC Conditions]

[1215] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Japan Chemical Industry Ecology-Toxicology & Information Center)

[1216] UV detection wavelength: 254 nm

[1217] Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile

[1218] Flow rate: 2.0 mL / min

[1219] Pump: LC-20AD (manufactured by Shimadzu Corporation), 2 units (high-pressure gradient)

[1220] Gradient condition: Elution is performed with the concentration gradient described in [Table LC1].

[1221] [Table 1]

[1222] [Table LC1]

[1223] Time (minutes) Liquid A (%) Liquid B (%) 0.01 90 10 2.00 0 100 4.00 0 100 4.01 90 10

[1224] [MS conditions]

[1225] Detector: LCMS-2020 (manufactured by Shimadzu Corporation)

[1226] Ionization method: DUIS

[1227] Reference Production Example 1

[1228] To a mixture of 0.5 g of ethyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-3-hydroxy-1H-pyrazole-5-carboxylate prepared according to the method described in International Publication No. 2013 / 192346 and 3 mL of N,N-dimethylformamide were added 1.1 g of cesium carbonate and 0.25 mL of 2-iodopropane, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.51 g of Intermediate 1.

[1229] [Chemical Formula 80]

[1230]

[1231] Intermediate 1: 11H-NMR (CDCl3) δ: 6.19 (1H, s), 4.98 (1H, br s), 4.73 - 4.64 (1H, m), 4.54 - 4.51 (2H, m), 4.32 (2H, q), 3.55 - 3.51 (2H, m), 1.41 (9H, s), 1.36 (3H, t), 1.35 - 1.34 (6H, m).

[1232] Reference Production Example 2

[1233] To a mixture of 0.51 g of Intermediate 1 and 5 mL of cyclopentyl methyl ether at 0 °C was added 6 mL of hydrogen chloride (cyclopentyl methyl ether solution of about 4 mol / L), and the mixture was stirred at room temperature for 4 hours. The resulting mixture was concentrated under reduced pressure. To the resulting residue was added saturated aqueous sodium carbonate solution, and the mixture was stirred at room temperature for 3 hours. Extraction was carried out with chloroform containing 25% 2-propanol. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.26 g of Intermediate 2.

[1234] [Chemical Formula 81]

[1235]

[1236] Intermediate 2: 1 1H-NMR (CDCl3) δ: 6.24 (1H, s), 6.17 (1H, br s), 4.73 - 4.64 (1H, m), 4.23 - 4.20 (2H, m), 3.78 - 3.74 (2H, m), 1.37 - 1.36 (3H, m), 1.36 - 1.34 (3H, m).

[1237] Reference Production Example 3

[1238] To a mixture of 5.9 g of ethyl 3-(trifluoromethyl)-1H-pyrazole-5-carboxylate and 70 mL of THF at 0 °C was added 9.0 g of triphenylphosphine, 5.3 mL of 2-(tert-butoxycarbonylamino)-1-ethanol, and 10 g of bis(2-methoxyethyl) azodicarboxylate. The mixture was stirred at room temperature for 6 hours, water was added, and extraction was carried out with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 7.8 g of Intermediate 3.

[1239] [Chemical Formula 82]

[1240]

[1241] Intermediate 3: 11H-NMR (CDCl3) δ: 7.09 (1H, s), 4.79 (1H, br s), 4.74 - 4.71 (2H, m), 4.37 (2H, q), 3.63 (2H, q), 1.40 - 1.37 (12H, m).

[1242] Reference Production Example 4

[1243] The following shows the compound produced using Intermediate 3 in place of Intermediate 1 and according to Reference Production Example 2 and its physical property values.

[1244] [Chemical Formula 83]

[1245]

[1246] Intermediate 4: 1 1H-NMR (CDCl3) δ: 7.12 (1H, s), 6.16 (1H, br s), 4.49 - 4.46 (2H, m), 3.87 - 3.83 (2H, m).

[1247] Reference Production Example 5

[1248] To a mixture of 23.4 g of ethyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-3-hydroxy-1H-pyrazole-5-carboxylate prepared according to the method described in International Publication No. 2013 / 192346, 150 mL of chloroform, and 170 mL of water at 0 °C, 86.2 g of potassium carbonate and 30.2 mL of (bromodifluoromethyl)trimethylsilane were added, and the mixture was stirred at room temperature for 4 hours. The resulting mixture was extracted with chloroform. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 5.5 g of Intermediate 5.

[1249] [Chemical Formula 84]

[1250]

[1251] Intermediate 5: 1 1H-NMR (CDCl3) δ: 6.79 (1H, t), 6.44 (1H, s), 4.80 (1H, br s), 4.59 - 4.57 (2H, m), 4.35 (2H, q), 3.56 - 3.55 (2H, m), 1.41 - 1.36 (12H, m).

[1252] Reference Production Example 6

[1253] The following shows the compound produced using Intermediate 5 in place of Intermediate 1 and according to Reference Production Example 2 and its physical property values.

[1254] [Chemical Formula 85]

[1255]

[1256] Intermediate 6: 1 H-NMR (CDCl3) δ: 6.79 (1H, t), 6.49 (1H, s), 6.00 - 5.91 (1H, m), 4.31 - 4.27 (2H, m), 3.82 - 3.78 (2H, m).

[1257] Reference Production Example 7

[1258] The following shows the compound produced using methyl 5-bromo-1H-pyrazole-3-carboxylate instead of ethyl 3-(trifluoromethyl)-1H-pyrazole-5-carboxylate and according to Reference Production Example 3, and its physical property values.

[1259] [Chemical Formula 86]

[1260]

[1261] Intermediate 7: 1 H-NMR (CDCl3) δ: 6.83 (1H, s), 4.82 (1H, s), 4.66 - 4.63 (2H, m), 3.89 (3H, s), 3.61 - 3.56 (2H, m), 1.41 (9H, s).

[1262] Reference Production Example 8

[1263] The following shows the compound produced using Intermediate 7 instead of Intermediate 1 and according to Reference Production Example 2, and its physical property values.

[1264] [Chemical Formula 87]

[1265]

[1266] Intermediate 8: 1 H-NMR (CDCl3) δ: 6.87 (1H, s), 6.03 (1H, br s), 4.40 - 4.37 (2H, m), 3.81 - 3.77 (2H, m).

[1267] Reference Production Example 9

[1268] Under an argon atmosphere, a mixture of 7.17 g of 3-bromo-2-chloro-5-(phenylmethoxy)pyridine, 0.55 g of tris(dibenzylideneacetone)dipalladium(0), 0.69 g of Xantphos, 6.84 mL of diisopropylamine, 1.95 mL of ethanethiol, and 70 mL of 1,4-dioxane was stirred at 80 °C for 3.5 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 6.47 g of Intermediate 9.

[1269] [Chemical Formula 88]

[1270]

[1271] Intermediate 9: 1 H-NMR (CDCl3) δ: 7.89 (1H, d), 7.42 - 7.35 (5H, m), 7.10 (1H, d), 5.11 (2H, s), 2.90 (2H, q), 1.35 (3H, t).

[1272] Reference Production Example 10

[1273] To a mixture of 6.5 g of Intermediate 9 and 100 mL of chloroform at 0 °C, 13.5 g of m-chloroperbenzoic acid was added little by little. After stirring at room temperature for 3 hours, the resulting mixture was added to water in which 18.6 g of sodium thiosulfate and 9.9 g of sodium bicarbonate were dissolved, and the mixture was stirred for 0.5 hour. Extraction of the resulting mixture was performed with chloroform, the obtained organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 7.7 g of Intermediate 10.

[1274] [Chemical Formula 89]

[1275]

[1276] Intermediate 10: 1 H-NMR (CDCl3) δ: 8.35 (1H, d), 8.01 (1H, d), 7.44 - 7.35 (5H, m), 5.18 (2H, s), 3.49 (2H, q), 1.27 (3H, t).

[1277] Reference Production Example 11

[1278] To a mixture of 6.86 g of Intermediate 10 and 65 mL of sulfolane was added 7.35 g of cesium fluoride, and the mixture was stirred at 160 °C for 8 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 3.13 g of Intermediate 11.

[1279] [Chemical Formula 90]

[1280]

[1281] Intermediate 11: LCMS: 296 [M+H]+, RT = 1.85 minutes

[1282] Reference Production Example 12

[1283] The following shows the compound produced using 3-bromo-2-chloro-5-(difluoromethoxy)pyridine in place of Intermediate 10 according to Reference Production Example 11 and its physical property values.

[1284] [Chemical Formula 91]

[1285]

[1286] Intermediate 12: 1 1H-NMR (CDCl3) δ: 8.04 - 8.03 (1H, m), 7.85 - 7.83 (1H, m), 6.53 (1H, t).

[1287] Reference Production Example 13

[1288] To a mixture of 3.9 g of Intermediate 6, 4.6 g of Intermediate 12 and 25 mL of dimethyl sulfoxide was added 12.5 g of cesium carbonate, and the mixture was stirred at 40 °C for 8 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 5.3 g of Intermediate 13.

[1289] [Chemical Formula 92]

[1290]

[1291] Intermediate 13: 1 1H-NMR (CDCl3) δ: 8.37 (1H, d), 7.86 (1H, d), 7.00 - 6.41 (3H, m), 4.51 - 4.41 (3H, m), 4.00 - 3.96 (1H, m).

[1292] Reference Production Example 14

[1293] The compounds prepared according to Reference Production Example 13 using Intermediate 4 in place of Intermediate 6 and using Intermediate 12 in place of 3-bromo-6-chloro-2-fluoropyridine, and their physical property values are shown below.

[1294] [Chemical Formula 93]

[1295]

[1296] Intermediate 14: 1 H-NMR (CDCl3) δ: 8.38 (1H, d), 7.87 (1H, d), 7.24 (1H, s), 6.60 (1H, t), 4.68 - 4.65 (2H, m), 4.52 - 4.45 (1H, m), 4.07 - 4.01 (1H, m).

[1297] Production Example 1

[1298] To a mixture of 0.26 g of Intermediate 2 and 5 mL of N,N-dimethylformamide were added 0.87 g of cesium carbonate and 1.1 g of 6-iodo-3-(ethylsulfonyl)imidazo[1,2-a]pyridine-2-fluoride prepared according to the method described in International Publication No. 2020 / 158889, and the mixture was stirred at 90 °C for 7.5 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.35 g of Compound 1 of the present invention.

[1299] [Chemical Formula 94]

[1300]

[1301] Compound 1 of the present invention: 1 H-NMR (CDCl3) δ: 9.09 - 9.09 (1H, m), 7.70 (1H, dd), 7.49 (1H, dd), 6.31 (1H, s), 4.78 - 4.69 (1H, m), 4.43 - 4.40 (2H, m), 4.29 - 4.26 (2H, m), 3.58 (2H, q), 1.45 (3H, t), 1.39 - 1.39 (3H, m), 1.38 - 1.37 (3H, m).

[1302] Production Example 1-1

[1303] The compounds prepared according to Production Example 1 and their physical property values are shown below.

[1304] [Chemical Formula 95]

[1305]

[1306] In the compound represented by formula (B-1), n, R 3b , R 3c and R 6b are any combination of the compounds described in [Table B-1].

[1307] [Table 2]

[1308] [Table B-1]

[1309] Compound of the present invention n <![CDATA[R 3b > <![CDATA[R 3c > <![CDATA[R 6b > 2 2 I H <![CDATA[CF3]]> 3 2 I H <![CDATA[OCHF2]]> 46 2 I H Br

[1310] Compound 2 of the present invention: 1H-NMR (CDCl3) δ: 9.08 - 9.07 (1H, m), 7.72 (1H, dd), 7.50 (1H, dd), 7.21 - 7.21 (1H, m), 4.67 (2H, t), 4.35 (2H, t), 3.56 (2H, q), 1.45 (3H, t).

[1311] Compound 3 of the present invention: 1H-NMR (CDCl3) δ: 9.07 - 9.06 (1H, m), 7.71 (1H, dd), 7.51 - 7.49 (1H, m), 6.83 (1H, t), 6.56 (1H, s), 4.50 - 4.47 (2H, m), 4.32 - 4.31 (2H, m), 3.56 (2H, q), 1.44 (3H, t).

[1312] Compound 46 of the present invention: 1H-NMR (CDCl3) δ: 9.08 - 9.07 (1H, m), 7.71 (1H, dd), 7.49 (1H, dd), 6.95 (1H, s), 4.59 - 4.56 (2H, m), 4.31 - 4.28 (2H, m), 3.55 (2H, q), 1.44 (3H, t).

[1313] Production Example 1-2

[1314] The following shows the compounds produced using 7,8-dihydroimidazo-[1,5-c]-pyrimidin-5(6H)-one instead of Intermediate 2 according to Production Example 1 and their physical property values.

[1315] [Chemical Formula 96]

[1316]

[1317] Compound 47 of the present invention: 1H-NMR (CDCl3) δ: 9.07 (1H, s), 8.20 (1H, s), 7.71 (1H, dd), 7.50 (1H, d), 6.90 (1H, s), 4.12 - 4.05 (2H, m), 3.55 (2H, q), 3.23 - 3.20 (2H, m), 1.46 (3H, t).

[1318] Production Example 2

[1319] To a mixture of 0.5 g of Intermediate 4 and 3 mL of dimethyl sulfoxide were added 1.6 g of...

Claims

1. A compound represented by formula (I) or an N-oxide thereof, [Chemical formula 1] In formula (I), Q represented by the following formula (wherein # represents a bonding site with a sulfur atom, and ● represents a bonding site with Het) represents a group represented by formula Q1 or a group represented by formula Q2, [Chemical formula 2] [Chemical formula 3] A 1 Represents nitrogen atom or CR 8 , R 8 represents a halogen atom or a hydrogen atom, R 2 represents a C1-C6 alkyl group, a cyclopropyl group, or a cyclopropylmethyl group which may be substituted with one or more halogen atoms, n represents 0, 1 or 2, G 1 Represents nitrogen atom or CR 3a , G 2 Represents nitrogen atom or CR 3b , G 3 Represents nitrogen atom or CR 3c , G 4 Represents nitrogen atom or CR 3d , R 3a , R 3b , R 3c and R 3d are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group L, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group E, a phenyl group which may be substituted by one or more substituents selected from group H, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group H, OR 12 NR 11 R 12 NR 11a R 12a NR 24 NR 11 R 12 NR 24 OR 11 NR 11 C(O)R 13 NR 24 NR11 C(O)R 13 、NR 11 C(O)OR 14 、NR 24 NR 11 C(O)OR 14 、NR 11 C(O)NR 31 R 32 、NR 24 NR 11 C(O)NR 31 R 32 、N=CHNR 31 R 32 、N=S(O) p R 15 R 16 、C(O)R 13 、C(O)OR 17 、C(O)NR 31 R 32 、C(O)NR 11 S(O)2R 23 、CR 30 =NOR 17 、NR 11 CR 24 =NOR 17 、S(O) m R 23 、 a cyano group, a nitro group, a halogen atom or a hydrogen atom, p represents 0 or 1, m represents 0, 1 or 2, R 30 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a halogen atom, OR 35 、NR 36 R 37 or a hydrogen atom, R 35 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 17 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from group D, or a hydrogen atom, R 11 、R 24 、R 36 and R 37 are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom, R 12Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from group J, a C3-C7 cycloalkenyl group that can be substituted by one or more substituents selected from group J, a phenyl group that can be substituted by one or more substituents selected from group D, a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group D, S(O)2R 23 or a hydrogen atom, R 23 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a phenyl group that can be substituted by one or more substituents selected from group D, R 11a and R 12a together with the nitrogen atom to which they are bonded form a 3-7 membered non-aromatic heterocyclic group that can be substituted by one or more substituents selected from group E, R 13 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that can be substituted by one or more halogen atoms, a phenyl group that can be substituted by one or more substituents selected from group D, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group D, or a hydrogen atom, R 14 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that can be substituted by one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group can be substituted by one or more substituents selected from group D}, R 15 and R 16 are the same or different from each other and represent a C1-C6 alkyl group that can be substituted by one or more halogen atoms, R 31 Represents a C1-C6 alkyl group that can be substituted by one or more halogen atoms, or a hydrogen atom, R 32 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from group J, S(O)2R 23 or a hydrogen atom, R 4 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group L 2 in, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from group E 2 in, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from group H 2phenyl substituted with more than one substituent in, 5- or 6-membered aromatic heterocyclic group substituted with more than one substituent selected from the group H 2 in, OR 42 , NR 41 R 42 , NR 41a R 42a , NR 54 NR 41 R 42 , NR 54 OR 41 , NR 41 C(O)R 43 , NR 54 NR 41 C(O)R 43 , NR 41 C(O)OR 44 , NR 54 NR 41 C(O)OR 44 , NR 41 C(O)NR 61 R 62 , NR 54 NR 41 C(O)NR 61 R 62 , N=CHNR 61 R 62 , N=S(O) r R 45 R 46 , C(O)R 43 , C(O)OR 47 , C(O)NR 61 R 62 , C(O)NR 41 S(O)2R 53 , CR 60 =NOR 47 , NR 41 CR 54 =NOR 47 , S(O) t R 53 , cyano, nitro or halogen atom, r represents 0 or 1, t represents 0, 1 or 2, R 60 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, halogen atom, OR 65 , NR 66 R 67 or hydrogen atom, R 65Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, R 47 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenyl group that can be substituted by one or more substituents selected from Group D 2 in, or a hydrogen atom, R 41 、R 54 、R 66 and R 67 are the same or different from each other and represent a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom, R 42 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from Group F 2 in, a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from Group J 2 in, a C3-C7 cycloalkenyl group that can be substituted by one or more substituents selected from Group J 2 in, a phenyl group that can be substituted by one or more substituents selected from Group D 2 in, a 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group D 2 in, a hydrogen atom or S(O)2R 53 , R 53 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a phenyl group that can be substituted by one or more substituents selected from Group D 2 in, R 41a and R 42a together with the nitrogen atom to which they are bonded form a 3-7 membered non-aromatic heterocyclic group that can be substituted by one or more substituents selected from Group E 2 in, R 43 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that can be substituted by one or more halogen atoms, a phenyl group that can be substituted by one or more substituents selected from Group D 2 in, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from Group D 2 in, or a hydrogen atom, R 44 Represents a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that can be substituted by one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety of the phenyl C1-C3 alkyl group can be selected from Group D 2substituted by one or more substituents selected from the group consisting of R 45 and R 46 which are the same as or different from each other and represent a C1-C6 alkyl group which may be substituted by one or more halogen atoms, R 61 represents a C1-C6 alkyl group which may be substituted by one or more halogen atoms or a hydrogen atom, R 62 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from the group consisting of F 2 a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from the group consisting of J 2 S(O)2R 53 or a hydrogen atom, k represents 0, 1, 2 or 3. When k is 2 or 3, the two or three Rs 4 may be the same or different, When two Rs 4 are bonded to adjacent carbon atoms, the two Rs 4 may together with the two carbon atoms to which they are bonded form a benzene ring, a pyrrole ring, a furan ring, a thiophene ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring or a pyrazine ring {the benzene ring, the pyrrole ring, the furan ring, the thiophene ring, the pyrazole ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the pyridine ring, the pyridazine ring, the pyrimidine ring and the pyrazine ring may be substituted by one or more substituents selected from the group consisting of H 2} or a triazole ring which may be substituted by one or more substituents selected from the group consisting of P, Het represents a group represented by formula Het1 or a group represented by formula Het2, [Chemical formula 4] A 2 represents -NR 5a -, or -CR 7a R 7b -, A 3 represents -CR 7c R 7d -, -CR 7e R 7f -CR 7g R 7h -* 1 or -CR 7i R 7j -CR 7k R 7l -CR 7m R 7n -*1 , * 1 represents the bonding position with A 2 . A 4 represents -NR 5b -, -CR 7o R 7p -, -CR 7q R 7r -CR 7s R 7t -* 2 , -NR 5c -CR 7u R 7v -* 2 , -CR 7w R 7x -CR 7y R 7z -CR 7aa R 7bb -* 2 , or -NR 5d -CR 7cc R 7dd -CR 7ee R 7ff -* 2 , * 2 represents the bonding position with A 2 . R 5a , R 5b , R 5c , and R 5d are the same as or different from each other, and represent a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group K, a C1-C6 alkoxy group that can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group that can be substituted by one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C6 alkyl group that can be substituted by one or more halogen atoms, or a hydrogen atom, R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g , R 7h , R 7i , R 7j , R 7k , R 7l , R 7m , R 7n , R 7o , R 7p , R 7q , R 7r, R 7s , R 7t , R 7u , R 7v , R 7w , R 7x , R 7y , R 7z , R 7aa , R 7bb , R 7cc , R 7dd , R 7ee and R 7ff are the same as or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C4 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a nitro group, OR 69 , NR 69 R 70 , a cyano group, a halogen atom or a hydrogen atom, R 7a and R 7b , R 7c and R 7d , R 7e and R 7f , R 7g and R 7h , R 7i and R 7j , R 7k and R 7l , R 7m and R 7n , R 7o and R 7p , R 7q and R 7r , R 7s and R 7t , R 7u and R 7v , R 7w and R 7x , R 7y and R 7z , R 7aa and R 7bb , R 7cc and R 7dd , and R 7ee and R 7ff may each, together with the carbon atom to which they are bonded, form a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, R 69represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group T, a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group U, a C3-C7 cycloalkenyl group which may be substituted by one or more substituents selected from group U, a phenyl group which may be substituted by one or more substituents selected from group V, a 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group V, or a hydrogen atom, R 70 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or a hydrogen atom, W represents an oxygen atom or a sulfur atom, B 1 represents CR 6a or a nitrogen atom, B 2 represents CR 6b or a nitrogen atom, B 3 represents CR 6c or a nitrogen atom, R 6a 、R 6b and R 6c are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from group L 3 a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from group E 3 a phenyl group which may be substituted by one or more substituents selected from group H 3 a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group H 3 OR 72 、NR 71 R 72 、NR 71a R 72a 、NR 84 NR 71 R 72 、NR 84 OR 71 、NR 71 C(O)R 73 、NR 84 NR 71 C(O)R 73 、NR 71 C(O)OR 74 、NR 84 NR 71 C(O)OR 74 、NR 71 C(O)NR 91 R 92 、NR 84 NR 71 C(O)NR91 R 92 、 N=CHNR 91 R 92 、 N=S(O) q R 75 R 76 、 C(O)R 73 、 C(O)OR 77 、 C(O)NR 91 R 92 、 C(O)NR 71 S(O)2R 83 、 CR 90 =NOR 77 、 NR 71 CR 84 =NOR 77 、 S(O) v R 83 、 a cyano group, a nitro group, a halogen atom or a hydrogen atom, q represents 0 or 1, v represents 0, 1 or 2, R 90 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a halogen atom, OR 95 、 NR 96 R 97 or a hydrogen atom, R 95 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 77 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group D 3 or a hydrogen atom, R 71 、 R 84 、 R 96 and R 97 are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms or a hydrogen atom, R 72 represents a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group F 3 a C3-C7 cycloalkyl group which may be substituted by one or more substituents selected from Group J 3 a C3-C7 cycloalkenyl group which may be substituted by one or more substituents selected from Group J 3 a phenyl group which may be substituted by one or more substituents selected from Group D 3 a 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group D 3 S(O)2R 83 or a hydrogen atom, R 83 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from Group D 3 below. R 71a and R 72a together with the nitrogen atom to which they are attached form a 3- to 7-membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from Group E 3 below. R 73 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group D 3 below, 3 a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D R 74 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenylC1-C3 alkyl group {the phenyl moiety of which may be substituted with one or more substituents selected from Group D 3 below}, R 75 and R 76 are the same or different from each other and represent a C1-C6 alkyl group which may be substituted with one or more halogen atoms, R 91 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, R 92 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F 3 below, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from Group J 3 below, S(O)2R 83 or a hydrogen atom, Group L: a group consisting of a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylthio group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, a cyano group, a hydroxyl group and a halogen atom Group M: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, and a halogen atom Group D: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group and a halogen atom R 21 and R 22 which are the same or different from each other, represent a C1-C6 alkyl group which may be substituted with one or more halogen atoms Group E: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group Group F: a group consisting of a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from Group M, an amino group, NHR 21 、NR 21 R 22 、a halogen atom and a cyano group Group H: a group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, OR 10 、NR 9 R 10 、C(O)R 10 、C(O)NR 9 R 10 、OC(O)R 9 、OC(O)OR9 , NR 10 C(O)R 9 , NR 10 C(O)OR 9 , C(O)OR 10 , a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group W R 9 represents a C1-C6 alkyl group that may be substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group that may be substituted with one or more halogen atoms R 10 represents a C1-C6 alkyl group that may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or more halogen atoms, or a hydrogen atom Group P: consisting of a C2-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that may be substituted with one or more halogen atoms, a phenyl group that may be substituted with one or more substituents selected from group D 2 among, a 5- or 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group D 2 among, a C2-C6 alkylcarbonyl group that may be substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group that may be substituted with one or more halogen atoms, an aminocarbonyl group, a (C1-C6 alkyl)aminocarbonyl group that may be substituted with one or more halogen atoms, a methyl group, and a di(C1-C4 alkyl)aminocarbonyl group that may be substituted with one or more halogen atoms Group J: consisting of a C1-C6 alkyl group that may be substituted with one or more halogen atoms, a halogen atom, and a cyano group Group K: consisting of a C1-C6 alkoxy group that may be substituted with one or more halogen atoms, a phenyl group that may be substituted with one or more substituents selected from group D, a 5- or 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group D, a C3-C7 cycloalkyl group that may be substituted with one or more halogen atoms, and a 3-7 membered non-aromatic heterocyclic group that may be substituted with one or more substituents selected from group M Group T: consisting of a C1-C6 alkoxy group that may be substituted with one or more halogen atoms, a phenyl group that may be substituted with one or more substituents selected from group D, a 5- or 6-membered aromatic heterocyclic group that may be substituted with one or more substituents selected from group D, a C3-C7 cycloalkyl group that may be substituted with one or more halogen atoms, a 3-7 membered non-aromatic heterocyclic group that may be substituted with one or more substituents selected from group M, an amino group, NHR 21 , NR 21 R 22 , a halogen atom, and a cyano group Group U: consisting of a C1-C6 alkyl group that may be substituted with one or more halogen atoms, a halogen atom, and a cyano group Group V: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group and a halogen atom, Group W: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group and a halogen atom, Group L 2 : a group consisting of a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, a cyano group, a hydroxyl group and a halogen atom, Group D 2: a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group and a halogen atom, Group E 2 : a group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group and a nitro group, Group F 2 : a group consisting of a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a 3-7 membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from Group M, an amino group, NHR 21 、NR 21 R 22 、a halogen atom and a cyano group, Group H 2 : a group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, OR 10 、NR 9 R 10 、C(O)R 10 、C(O)NR 9 R 10 、OC(O)R 9 、OC(O)OR 9 、NR 10 C(O)R 9 、NR 10 C(O)OR 9 、C(O)OR 10 、a halogen atom, a nitro group, a cyano group, an amino group and a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group W, Group J2 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, a halogen atom, and a cyano group, Group L 3 : The group consisting of a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted by one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom, Group D 3 : The group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a thioalkyl group, a C1-C6 alkylthio group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted by one or more halogen atoms, an amino group, NHR 21 、NR 21 R 22 、C(O)R 21 、OC(O)R 21 、C(O)OR 21 、a cyano group, a nitro group, and a halogen atom, Group E 3 : The group consisting of a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted by one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted by one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group, Group F 3 : The group consisting of a C1-C6 alkoxy group which may be substituted by one or more halogen atoms, a phenyl group which may be substituted by one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from Group D, a C3-C7 cycloalkyl group which may be substituted by one or more halogen atoms, a 3-7-membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from Group M, an amino group, NHR 21 、NR 21 R 22 、a halogen atom, and a cyano group, Group H 3 : The group consisting of a C1-C6 alkyl group which may be substituted by one or more halogen atoms, OR10 , NR 9 R 10 , C(O)R 10 , C(O)NR 9 R 10 , OC(O)R 9 , OC(O)OR 9 , NR 10 C(O)R 9 , NR 10 C(O)OR 9 , C(O)OR 10 , a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from the group W Group J 3 : a group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a halogen atom, and a cyano group 2. The compound or its N-oxide according to claim 1, wherein Q is a group represented by formula Q1.

3. The compound or its N-oxide according to claim 1, wherein Q is a group represented by formula Q2.

4. The compound or its N-oxide according to claim 1, wherein Q is a group represented by formula Q1, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom or CR 3d .

5. The compound or its N-oxide according to claim 1, wherein Q is a group represented by formula Q1, G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is CR 3d .

6. The compound or its N-oxide according to claim 1, wherein Q is a group represented by formula Q2, and A 1 is a nitrogen atom.

7. The compound or its N-oxide according to claim 1, wherein Q is a group represented by formula Q2, A 1 is CR 8 .

8. The compound or its N-oxide according to any one of claims 1 to 7, wherein Het is a group represented by Het1, A 2 is -CR 7a R 7b -, A 3 is -CR 7c R 7d - or -CR 7e R 7f -CR 7g R 7h -*, 1 and W is an oxygen atom.

9. The compound or its N-oxide according to any one of claims 1 to 7, wherein Het is a group represented by formula Het2, A 2 is -CR 7a R 7b -, A 4 is -CR 7o R 7p - or -CR 7q R 7r -CR 7s R 7t -*, 2 and W is an oxygen atom.

10. A composition for controlling harmful arthropods, which contains an inert carrier and the compound or its N-oxide according to any one of claims 1 to 9 11. A composition, which contains one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound or its N-oxide according to any one of claims 1 to 9 Group (a): a group consisting of an insecticidal active ingredient, a acaricidal active ingredient, and a nematicidal active ingredient Group (b): a bactericidal active ingredient Group (c): a plant growth regulating ingredient Group (d): Repellent component.

12. A method for controlling harmful arthropods, wherein An effective amount of the compound or its N-oxide according to any one of claims 1 to 9 or an effective amount of the composition according to claim 11 is applied to harmful arthropods or their habitats.

13. A seed or vegetative propagating organ which retains an effective amount of the compound or its N-oxide according to any one of claims 1 to 9 or an effective amount of the composition according to claim 11.

14. A compound of formula (II) or a salt thereof, [Chemical formula 5] In formula (II), X 1 represents a chlorine atom, a bromine atom, an iodine atom or a hydroxyl group, and the other symbols have the same meanings as in claim 1.

15. A compound of formula (III) or a salt thereof, [Chemical formula 6] In formula (III), X 2 represents a chlorine atom, a bromine atom, an iodine atom or a hydroxyl group, and the other symbols have the same meanings as in claim 1.

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