Heterocyclic compounds and harmful arthropod control compositions containing the same

Abstract

The present application provides a compound having an excellent control effect on harmful arthropods. A compound represented by formula (I) or its nitroxide has an excellent control effect on harmful arthropods. [In the formula, Z represents an oxygen atom, G 1 represents CR 3a , etc., G 2 represents CR 3b , etc., G 3 represents CR 3c , etc., G 4 represents CR 3d , etc., A 1 represents CR 4a , etc., A 2 represents CR 4b , etc., A 3 represents CR 4c , etc., A 4 represents CR 4d , etc., A 5 represents CR 4e , etc., R 1 represents C1-C6 chain hydrocarbon group, etc., R 2 represents C1-C6 alkyl group, etc., R 3a , R 3b , R 3c , and R 3d are the same or different, represent C1-C6 chain hydrocarbon group, etc., R 4a , R 4b , R 4c , R 4d , and R 4e are the same or different, represent C1-C6 chain hydrocarbon group, etc., n represents 0, 1 or 2.]

Description

TECHNICAL FIELD

[0001] This application claims priority to and the benefit of Japanese Patent Application No. 2020-165684 filed September 30, 2020, and Japanese Patent Application No. 2021-102389 filed June 21, 2021, the entire contents of which are incorporated herein by reference.

[0002] The present application relates to a heterocyclic compound and a harmful arthropod control composition containing the same. BACKGROUND

[0003] Hitherto, various compounds have been studied for the purpose of controlling harmful arthropods. For example, it is described in Patent Literature 1 that a certain compound has a harmful organism control effect.

[0004] PRIOR ART DOCUMENTS

[0005] PATENT LITERATURE

[0006] Patent Literature 1: International Publication No. 2016 / 129684 SUMMARY

[0007] An object of the present application is to provide a compound having an excellent control effect on harmful arthropods.

[0008] The present application is as follows.

[0009] [1] A compound represented by formula (I) (hereinafter, referred to as the present compound P) or a nitroxide thereof (hereinafter, the compound represented by formula (I) or the nitroxide thereof is referred to as the present compound X).

[0010]

[0011] [In the formula,

[0012] Z represents an oxygen atom or a sulfur atom,

[0013] R 1 represents a C1-C6 chain hydrocarbon group which can be substituted with one or more substituents selected from Group W, a C3-C7 cycloalkyl group which can be substituted with one or more substituents selected from Group U, a phenyl group which can be substituted with one or more substituents selected from Group V, a five- or six-membered aromatic heterocyclic group which can be substituted with one or more substituents selected from Group V, C(O)R 51 , C(O)OR 51 , or C(O)NR 51 R 52 ,

[0014] R 51 and R 52the same or different, represent a C1-C6 chain hydrocarbon group which can be substituted with one or more halogen atoms, a phenyl group which can be substituted with one or more substituents selected from Group V, a five- or six-membered heterocyclic group which can be substituted with one or more substituents selected from Group V, or a hydrogen atom,

[0015] R 2 represents a C1-C6 alkyl group which can be substituted with one or more halogen atoms, a cyclopropyl group, or a cyclopropylmethyl group,

[0016] n represents 0, 1 or 2,

[0017] G 1 represents a nitrogen atom or CR 3a ,

[0018] G 2 represents a nitrogen atom or CR 3b ,

[0019] G 3 represents a nitrogen atom or CR 3c ,

[0020] G 4 represents a nitrogen atom or CR 3d ,

[0021] R 3a , R 3b , R 3c and R 3d the same or different, represent a C1-C6 chain hydrocarbon group which can be substituted with one or more substituents selected from Group B, a C3-C7 cycloalkyl group which can be substituted with one or more substituents selected from Group E, a phenyl group which can be substituted with one or more substituents selected from Group H, a five- or six-membered aromatic heterocyclic group which can be substituted with 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 NR 11 C(O)OR 14 , NR 11 C(O)NR31 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 hydrogen atom, or a halogen atom,

[0022] p represents 0 or 1,

[0023] m represents 0, 1 or 2,

[0024] R 30 represents a C1-C6 chain hydrocarbon group which can be substituted with 1 or more halogen atoms, a halogen atom, OR 35 , NR 36 R 37 , or a hydrogen atom,

[0025] R 35 represents a C1-C6 chain hydrocarbon group which can be substituted with 1 or more halogen atoms,

[0026] R 17 represents a C1-C6 chain hydrocarbon group which can be substituted with 1 or more halogen atoms, a phenyl group which can be substituted with 1 or more substituents selected from Group D, or a hydrogen atom,

[0027] R 11 , R 24 , R 36 and R 37 are the same or different and represent a C1-C6 chain hydrocarbon group which can be substituted with 1 or more halogen atoms, or a hydrogen atom,

[0028] R 12represents a C1-C6 straight chain alkyl group which can be substituted by one or more substituents selected from Group F, a C3-C7 cycloalkyl group which can be substituted by one or more substituents selected from Group J, a C3-C7 cycloalkenyl group which can be substituted by one or more substituents selected from Group J, a phenyl group which can be substituted by one or more substituents selected from Group D, a six-membered aromatic heterocyclic group which can be substituted by one or more substituents selected from Group D, a hydrogen atom, or S(O)2R 23 ,

[0029] R 23 represents a C1-C6 straight chain alkyl group which can be substituted by one or more halogen atoms, or a phenyl group which can be substituted by one or more substituents selected from Group D,

[0030] R 11a and R 12a together with the nitrogen atom to which they are bound form a three- to seven-membered non-aromatic heterocyclic group which can be substituted by one or more substituents selected from Group E,

[0031] R 13 represents a C1-C6 straight chain alkyl group which can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which can be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which can be substituted by one or more halogen atoms, a phenyl group which can be substituted by one or more substituents selected from Group D, a five- or six-membered aromatic heterocyclic group which can be substituted by one or more substituents selected from Group D, or a hydrogen atom,

[0032] R 14 represents a C1-C6 straight chain alkyl group which can be substituted by one or more halogen atoms, a C3-C7 cycloalkyl group which can be substituted by one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which can be substituted by one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety of which can be substituted by one or more substituents selected from Group D},

[0033] R 15 and R 16 are the same or different and represent a C1-C6 alkyl group which can be substituted by one or more halogen atoms,

[0034] R 31 represents a C1-C6 alkyl group which can be substituted by one or more halogen atoms, or a hydrogen atom,

[0035] R 32 represents a C1-C6 straight chain alkyl group which can be substituted by one or more substituents selected from Group F, a C3-C7 cycloalkyl group which can be substituted by one or more substituents selected from Group J, S(O)2R 23 , or a hydrogen atom,

[0036] A 1 represents a nitrogen atom or CR 4a ,

[0037] A 2 represents a nitrogen atom or CR 4b ,

[0038] A 3 represents a nitrogen atom or CR 4c ,

[0039] A 4 represents a nitrogen atom or CR 4d ,

[0040] A 5 represents a nitrogen atom or CR 4e (wherein, not all of A 2 , A 3 and A 4 represent a nitrogen atom),

[0041] R 4a and R 4e are the same or different, and represent a C1-C6 chain hydrocarbon group which can be substituted with 1 or more substituents selected from Group X, a C3-C6 cycloalkyl group which can be substituted with 1 or more substituents selected from Group Y, a phenyl group which can be substituted with 1 or more substituents selected from Group Z, a 5- or 6-membered heterocyclic group which can be substituted with 1 or more substituents selected from Group Z, OR 44 , S(O) k R 41 , S(O)2NR 41 R 42 , NR 41 R 43 , NR 41 C(O)R 42 , NR 41 C(O)OR 42 , NR 41 S(O)2R 43 , C(O)R 41 , C(O)OR 41 , C(O)NR 41 R 42 , CR 42 =NOR 41 , a hydroxyl group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom,

[0042] A 5 is CR 4e , R 4e and R 1 may together form -NR 45 -CR 41 R42 - #{# indicates the bonding position to the nitrogen atom to which R 1 is bonded,

[0043] R 4b , R 4c and R 4d are the same or different, and represent a C1-C6 chain hydrocarbon group which can be substituted with 1 or more substituents selected from Group X, a C3-C6 cycloalkyl group which can be substituted with 1 or more substituents selected from Group Y, a phenyl group which can be substituted with 1 or more substituents selected from Group Z, a 5- or 6-membered heterocyclic group which can be substituted with 1 or more substituents selected from Group Z, OR 44 , S(O) q R 41 , S(O)2NR 41 R 42 , NR 41 R 42 , NR 41 C(O)R 42 , NR 41 C(O)OR 42 , NR 41 S(O)2R 43 , C(O)R 41 , C(O)OR 41 , C(O)NR 41 R 42 , CR 42 =NOR 41 , a hydroxyl group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom (wherein, not all of R 4a , R 4b , R 4c , R 4d and R 4e all represent a hydrogen atom),

[0044] k represents 0, 1 or 2

[0045] q represents 0, 1 or 2,

[0046] R 41 and R 42 are the same or different, and represent a C1-C6 chain hydrocarbon group which can be substituted with 1 or more halogen atoms, a phenyl group which can be substituted with 1 or more substituents selected from Group Z, a 5- or 6-membered heterocyclic group which can be substituted with 1 or more substituents selected from Group Z, or a hydrogen atom,

[0047] R 43 represents a C1-C6 chain hydrocarbon group which can be substituted with 1 or more halogen atoms, a phenyl group which can be substituted with 1 or more substituents selected from Group Z, or a 5- or 6-membered heterocyclic group which can be substituted with 1 or more substituents selected from Group Z,

[0048] R 44 represents a C1-C6 chain hydrocarbon group which can be substituted with one or more halogen atoms,

[0049] R 45 represents a C1-C6 chain hydrocarbon group which can be substituted with one or more substituents selected from the group W 2 , a C3-C7 cycloalkyl group which can be substituted with one or more substituents selected from the group Y, a phenyl group which can be substituted with one or more substituents selected from the group Z, a five- or six-membered aromatic heterocyclic group which can be substituted with one or more substituents selected from the group Z, C(O)R 46 , C(O)OR 46 , C(O)NR 46 R 47 , or a hydrogen atom,

[0050] R 46 and R 47 are the same or different, and represent a C1-C6 chain hydrocarbon group which can be substituted with one or more halogen atoms, a phenyl group which can be substituted with one or more substituents selected from the group Z, a five- or six-membered heterocyclic group which can be substituted with one or more substituents selected from the group Z, or a hydrogen atom.

[0051] Group B: a group consisting of a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which can be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which can be substituted with one or more halogen atoms, a C1-C6 alkylthio group which can be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which can be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which can be substituted with one or more halogen atoms, a cyano group, a hydroxyl group, and a halogen atom.

[0052] Group C: a group consisting of a C1-C6 chain hydrocarbon group which can be substituted with one or more halogen atoms, a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which can be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which can be substituted with one or more halogen atoms, and a halogen atom.

[0053] Group D: a group consisting of C1-C6 chain hydrocarbon group which can be substituted with one or more halogen atoms, hydroxy group, C1-C6 alkoxy group which can be substituted with one or more halogen atoms, C3-C6 alkenyloxy group which can be substituted with one or more halogen atoms, C3-C6 alkynyloxy group which can be substituted with one or more halogen atoms, mercapto group, C1-C6 alkylthio group which can be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl group which can be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl group which can be substituted with one or more halogen atoms, amino group, NHR 21 , NR 21 R 22 , C(O)R 21 , OC(O)R 21 , C(O)OR 21 , cyano group, nitro group and halogen atom.

[0054] R 21 and R 22 are the same or different, and represent C1-C6 alkyl group which can be substituted with one or more halogen atoms.

[0055] Group E: a group consisting of C1-C6 chain hydrocarbon group which can be substituted with one or more halogen atoms, C1-C6 alkoxy group which can be substituted with one or more halogen atoms, C3-C6 alkenyloxy group which can be substituted with one or more halogen atoms, C3-C6 alkynyloxy group which can be substituted with one or more halogen atoms, halogen atom, oxo group, hydroxy group, cyano group and nitro group.

[0056] Group F: a group consisting of C1-C6 alkoxy group which can be substituted with one or more halogen atoms, phenyl group which can be substituted with one or more substituents selected from Group D, five- or six-membered aromatic heterocyclic group which can be substituted with one or more substituents selected from Group D, C3-C7 cycloalkyl group which can be substituted with one or more halogen atoms, three- to seven-membered non-aromatic heterocyclic group which can be substituted with one or more substituents selected from Group C, amino group, NHR 21 , NR 21 R 22 , halogen atom and cyano group.

[0057] Group H: a group consisting of C1-C6 alkyl group which can be substituted with one or more halogen atoms, five- or six-membered aromatic heterocyclic group which can be substituted with one or more substituents selected from Group D, 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)R9 NR 10 C(O)OR 9 NR 10 halogen atom, nitro group, cyano group and amino group.

[0058] R 9 C1-C6 alkyl group which can be substituted with 1 or more halogen atoms, or C3-C6 cycloalkyl group which can be substituted with 1 or more halogen atoms,

[0059] R 10 C1-C6 alkyl group which can be substituted with 1 or more halogen atoms, C3-C6 cycloalkyl group which can be substituted with 1 or more halogen atoms, or hydrogen atom.

[0060] Group J: a group consisting of C1-C6 alkyl group which can be substituted with 1 or more halogen atoms, halogen atom and cyano group.

[0061] Group U: a group consisting of C1-C6 alkyl group which can be substituted with 1 or more halogen atoms, C1-C6 alkoxy group which can be substituted with 1 or more halogen atoms, C1-C6 alkylthio group which can be substituted with 1 or more halogen atoms, C1-C6 alkylsulfinyl group which can be substituted with 1 or more halogen atoms, C1-C6 alkylsulfonyl group which can be substituted with 1 or more halogen atoms, and halogen atom.

[0062] Group V: a group consisting of C1-C6 alkyl group which can be substituted with 1 or more halogen atoms, C1-C6 alkoxy group which can be substituted with 1 or more halogen atoms, C1-C6 alkylthio group which can be substituted with 1 or more halogen atoms, C1-C6 alkylsulfinyl group which can be substituted with 1 or more halogen atoms, C1-C6 alkylsulfonyl group which can be substituted with 1 or more halogen atoms, C1-C6 alkylamino group which can be substituted with 1 or more halogen atoms, di(C1-C6 alkyl)amino group which can be substituted with 1 or more halogen atoms, C2-C6 alkylcarbonyl group which can be substituted with 1 or more halogen atoms, C2-C6 alkoxycarbonyl group which can be substituted with 1 or more halogen atoms, hydroxyl group, mercapto group, amino group, cyano group, nitro group and halogen atom.

[0063] Group W: a group consisting of C3-C6cycloalkyl which can be substituted by one or more substituents selected from a halogen atom and a C1-C3alkyl group, C1-C6alkoxy which can be substituted by one or more halogen atoms, C1-C6alkylthio which can be substituted by one or more halogen atoms, C1-C6alkylsulfinyl which can be substituted by one or more halogen atoms, C1-C6alkylsulfonyl which can be substituted by one or more halogen atoms, C2-C6alkylcarbonyl which can be substituted by one or more halogen atoms, C2-C6alkoxycarbonyl which can be substituted by one or more halogen atoms, phenyl which can be substituted by one or more substituents selected from Group Z, five- or six-membered aromatic heterocyclic group which can be substituted by one or more substituents selected from Group Z, hydroxy, cyano and a halogen atom.

[0064] Group X: a group consisting of C3-C6cycloalkyl which can be substituted by one or more substituents selected from a halogen atom and a C1-C3alkyl group, C1-C6alkoxy which can be substituted by one or more halogen atoms, C1-C6alkylthio which can be substituted by one or more halogen atoms, C1-C6alkylsulfinyl which can be substituted by one or more halogen atoms, C1-C6alkylsulfonyl which can be substituted by one or more halogen atoms, C2-C6alkylcarbonyl which can be substituted by one or more halogen atoms, C2-C6alkoxycarbonyl which can be substituted by one or more halogen atoms, hydroxy, mercapto, cyano and a halogen atom.

[0065] Group Y: a group consisting of C1-C6alkyl which can be substituted by one or more halogen atoms, C1-C6alkoxy which can be substituted by one or more halogen atoms, C1-C6alkylthio which can be substituted by one or more halogen atoms, C1-C6alkylsulfinyl which can be substituted by one or more halogen atoms, C1-C6alkylsulfonyl which can be substituted by one or more halogen atoms and a halogen atom.

[0066] Group Z: a group consisting of C1-C6alkyl which can be substituted by one or more halogen atoms, C1-C6alkoxy which can be substituted by one or more halogen atoms, C1-C6alkylthio which can be substituted by one or more halogen atoms, C1-C6alkylsulfinyl which can be substituted by one or more halogen atoms, C1-C6alkylsulfonyl which can be substituted by one or more halogen atoms, C1-C6alkylamino which can be substituted by one or more halogen atoms, di(C1-C6alkyl)amino which can be substituted by one or more halogen atoms, C2-C6alkylcarbonyl which can be substituted by one or more halogen atoms, C2-C6alkoxycarbonyl which can be substituted by one or more halogen atoms, hydroxy, mercapto, amino, cyano, nitro and a halogen atom.

[0067] Group W 2: C3-C6 cycloalkyl which can be substituted with one or more substituents selected from the group consisting of halogen atom and C1-C3 alkyl group, C1-C6 alkoxy which can be substituted with one or more halogen atoms, C1-C6 alkylthio which can be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl which can be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl which can be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl which can be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl which can be substituted with one or more halogen atoms, phenyl which can be substituted with one or more substituents selected from the group Z, five- or six-membered aromatic heterocyclic group which can be substituted with one or more substituents selected from the group Z, hydroxy, mercapto, cyano and halogen atom.

[0068] [2] The compound according to [1] (hereinafter, referred to as the present compound N) or its nitroxide (hereinafter, the present compound N or its nitroxide will be referred to as the present compound), wherein R 45 is C1-C6 chain hydrocarbon group which can be substituted with one or more substituents selected from the group X, C3-C7 cycloalkyl which can be substituted with one or more substituents selected from the group Y, phenyl which can be substituted with one or more substituents selected from the group Z, five- or six-membered aromatic heterocyclic group which can be substituted with one or more substituents selected from the group Z, C(O)R 46 , C(O)OR 46 , C(O)NR 46 R 47 , or hydrogen atom.

[0069] [3] The compound according to [1] or [2] or its nitroxide, wherein G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is nitrogen atom or CR 3d .

[0070] [4] The compound according to any one of [1] to [3] or its nitroxide, wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is nitrogen atom or CR 4c , A 4 is nitrogen atom or CR 4d , A 5 is nitrogen atom or CR 4e .

[0071] [5] The compound according to any one of [1] to [3], or a nitroxide thereof, wherein A 1 , A 2 , A 3 , A 4 , and A 5 are combined as follows:

[0072] A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is CR 4e ;

[0073] A 1 is CR 4a , A 2 is CR 4b , A 3 is a nitrogen atom, A 4 is CR 4d , A 5 is CR 4e ;

[0074] A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom, A 5 is CR 4e ;

[0075] A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is a nitrogen atom.

[0076] [6] The compound according to any one of [1] to [3], or a nitroxide thereof, wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A5 CR 4e .

[0077] [7] The compound according to [1] or [2], or a nitroxide thereof, wherein G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d ,

[0078] A 1 CR 4a , A 2 CR 4b , A 3 CR 4c , A 4 CR 4d , A 5 CR 4e .

[0079] [8] The compound according to any one of [1] to [7], or a nitroxide thereof, wherein R 2 is an ethyl group.

[0080] [9] The compound according to any one of [1] to [8], or a nitroxide thereof, wherein Z is an oxygen atom.

[0081]

[10] A harmful arthropod control composition comprising the compound according to any one of [1] to [9], or a nitroxide thereof.

[0082]

[11] A composition comprising one or more components selected from the group (a), the group (b), the group (c) and the group (d), and the compound according to any one of [1] to [9], or a nitroxide thereof,

[0083] Group (a): a group consisting of an insecticidal active ingredient, a miticidal active ingredient and a nematicidal active ingredient;

[0084] Group (b): a fungicidal active ingredient;

[0085] Group (c): a plant growth regulating ingredient;

[0086] Group (d): a repellent ingredient.

[0087]

[12] A method for controlling a harmful arthropod, comprising applying an effective amount of the compound according to any one of [1] to [9], or a nitroxide thereof, or an effective amount of the composition according to

[11] to a harmful arthropod or a habitat of a harmful arthropod.

[0088]

[13] A seed or vegetative propagule, which retains an effective amount of the compound or nitroxide thereof according to any one of [1] to [9], or an effective amount of the composition according to

[11] .

[0089]

[14] A compound represented by formula (II) or a salt thereof (hereinafter, the compound represented by formula (II) or a salt thereof is referred to as Intermediate A).

[0090]

[0091] [In the formula, the symbols represent the same meanings as described above.]

[0092] According to the present application, harmful arthropods can be controlled. DETAILED DESCRIPTION

[0093] The substituents in the present application are described.

[0094] A halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0095] When the substituent is substituted with two or more halogen atoms or substituents, these halogen atoms or substituents can be the same or different.

[0096] In the present specification, the notation "C X-C Y" means the number of carbon atoms is X to Y. For example, the notation "C1-C6" means the number of carbon atoms is 1 to 6.

[0097] A chain hydrocarbon group means an alkyl group, an alkenyl group or an alkynyl group.

[0098] As the alkyl group, for example, there are mentioned 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 t-butyl group, a pentyl group and a hexyl group.

[0099] As the alkenyl group, for example, there are mentioned 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.

[0100] As the alkynyl group, for example, there are mentioned 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.

[0101] As the alkoxy group, for example, there are mentioned a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a t-butoxy group, a pentoxy group and a hexyloxy group.

[0102] As the alkenyloxy group, for example, there are mentioned a 2-propenyloxy group, a 2-butenyloxy group and a 5-hexenyloxy group.

[0103] As the alkynyl group, for example, a 2-propynyl group, a 2-butynyl group and a 5-hexynyl group can be given.

[0104] As the cycloalkyl group, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cycloheptyl group can be given.

[0105] As the cycloalkenyl group, for example, a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group and a cycloheptenyl group can be given.

[0106] The three- to seven-membered non-aromatic heterocyclic group means an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an is oxazolidine ring, a 1,3- oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring or a 1,4-thiazepane ring.

[0107] As the three- to seven-membered non-aromatic heterocyclic group which can be substituted with one or more substituents selected from Group E, for example, the groups shown below can be given.

[0108]

[0109] The five- or six-membered aromatic heterocyclic group means a five-membered aromatic heterocyclic group or a six-membered aromatic heterocyclic group. The five-membered aromatic heterocyclic group means a pyrrolyl group, a furanyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an is oxazolyl group, a thiazolyl group, an isothiazolyl group, a diazolyl group or a thiadiazolyl group, and the six-membered aromatic heterocyclic group means a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group or a tetrazinyl group.

[0110] The five- or six-membered heterocyclic group means a five- or six-membered aromatic heterocyclic group or a five- or six-membered non-aromatic heterocyclic group, and for example, a pyrrolyl group, a furanyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an is oxazolyl group, a thiazolyl group, an isothiazolyl group, a diazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a pyrrolidinyl group, an imidazolinyl group, an imidazolidinyl group, a piperidinyl group, a tetrahydropyrimidinyl group, a hexahydropyrimidinyl group, a piperazinyl group, an oxazolidinyl group, an is oxazolidinyl group, a 1,3- oxazinanly group, a morpholinyl group, a thiazolidinyl group, an isothiazolidinyl group, a 1,3-thiazinanly group and a thiomorpholinyl group.

[0111] Examples of (C3-C6 cycloalkyl)C1-C3 alkyl groups that can be substituted with one or more halogen atoms include cyclopropylmethyl, (2-fluorocyclopropyl)methyl, cyclopropyl(fluoro)methyl and (2-fluorocyclopropyl)(fluoro)methyl.

[0112] As a phenyl C1-C3 alkyl group {the phenyl portion of which may be substituted by one or more substituents selected from group D}, examples include benzyl, 2-fluorobenzyl, 4-chlorobenzyl, 4-(trifluoromethyl)benzyl and 2-[4-(trifluoromethyl)phenyl]ethyl.

[0113] Examples of alkyl thio groups include methyl thio, ethyl thio, propyl thio, and isopropyl thio.

[0114] Examples of alkyl sulfinyl groups include methyl sulfinyl, ethyl sulfinyl, propyl sulfinyl, and isopropyl sulfinyl.

[0115] Examples of alkyl sulfonyl groups include, for example, methyl sulfonyl, ethyl sulfonyl, propyl sulfonyl, and isopropyl sulfonyl.

[0116] Examples of alkylamino groups include, for example, methylamino, ethylamino, isopropylamino, and hexylamino.

[0117] Examples of dialkylamino compounds include, for example, dimethylamino, ethylmethylamino, isopropylmethylamino, and dihexylamino.

[0118] Examples of alkyl carbonyl groups include acetyl, propionyl, 2-methylpropionyl, and hexanoyl.

[0119] Examples of alkoxycarbonyl groups include, for example, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, and pentoxycarbonyl.

[0120] R 4a R 4b R 4c R 4d and R 4e In the middle, "among which, not all existing R..." 4a R 4b R 4c R 4d and R 4e "Both indicate hydrogen atoms" refers to the presence of A 1 A 2 A 3 A 4 and A 5 The six-membered ring (i.e., phenyl or six-membered aromatic heterocyclic group) has one or more substituents, indicating the presence of R. 4a R4b at least one of R 4c at least one of R 4d and R 4e is not a hydrogen atom. For example, in the compounds wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is CR 4e , the case wherein all of R 4a , R 4b , R 4c , R 4d and R 4e are hydrogen atoms is excluded, and in the compounds wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom, A 5 is CR 4e , the case wherein all of R 4a , R 4b , R 4c and R 4e are hydrogen atoms is excluded.

[0121] In other words, in the formula (I) or the formula (II), neither the phenyl group nor the six-membered aromatic heterocyclic group represented by the formula (I-P) is unsubstituted.

[0122]

[0123] [In the formula, the wavy line portion represents the bonding position to C(Z), and the other symbols represent the same meanings as described above.]

[0124] As the nitroxide of the compound represented by the formula (I), for example, a compound represented by the following formula can be given.

[0125]

[0126] [In the formula, the symbols represent the same meanings as described above.]

[0127] The compound X and the intermediate A of the present application sometimes exist as one or more stereoisomers. As the stereoisomers, enantiomers, diastereomers and geometric isomers, etc. can be given. The compound X and the intermediate A of the present application include each stereoisomer and a mixture of stereoisomers in an arbitrary ratio.

[0128] The compound X of the present application and the compound represented by formula (II) sometimes form an acid addition salt. As the acid to form the acid addition salt, for example, there are hydrogen chloride, phosphoric acid, sulfuric acid and the like inorganic acids, and acetic acid, trifluoroacetic acid, benzoic acid, p-toluenesulfonic acid and the like organic acids. The acid addition salt is obtained by mixing the compound X of the present application or the compound represented by formula (II) with an acid.

[0129] As the compound N of the present application, the following compounds can be given.

[0130] [Mode 1] The compound N of the present application is a compound in which 1 is a C1-C6 chain hydrocarbon group which can be substituted with one or more substituents selected from Group W, A 5 is CR 4e , R 4e and R 1 may form together -NR 45 -CR 41 R 42 -#, R 41 and R 42 are the same or different and are a C1-C6 chain hydrocarbon group which can be substituted with one or more halogen atoms or a hydrogen atom, R 45 is a C1-C6 chain hydrocarbon group which can be substituted with one or more substituents selected from Group X or a hydrogen atom.

[0131] [Mode 2] The compound N of the present application is a compound in which 1 is a C1-C6 alkyl group, A 5 is CR 4e , R 4e and R 1 may form together -NR 45 -CR 41 R 42 -#, R 41 , R 42 and R 45 are the same or different and are a C1-C6 alkyl group or a hydrogen atom.

[0132] [Mode 3] The compound N of the present application is a compound in which 1 , G 2 , G 3 and G 4 are combined as follows: G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom or CR 3d ; G 1 is a nitrogen atom, G 2 is CR3b , G 3 is CR 3c , G 4 is CR 3d in combination; G 1 is CR 3a , G 2 is a nitrogen atom, G 3 is CR 3c , G 4 is CR 3d in combination; or G 1 is CR 3a , G 2 is CR 3b , G 3 is a nitrogen atom, G 4 is CR 3d in combination, R 3a , R 3c and R 3d are each a hydrogen atom, R 3b is a C1-C6 alkyl group which can be substituted with 1 or more halogen atoms or a halogen atom.

[0133] [Mode 4] The compound N of the present application is a compound wherein G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom or CR 3d and R 3a , R 3c and R 3d are each a hydrogen atom, R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group can be substituted with 1 or more substituents selected from a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group can be substituted with 1 or more halogen atoms}, a halogen atom or a hydrogen atom.

[0134] [Mode 5] The compound N of the present application is a compound wherein G 1 is CR 3a , G 2 is CR 3b , G 3 is CR 3c , G 4 is a nitrogen atom or CR 3d and R 3a , R 3c and R 3d are each a hydrogen atom, R 3ba compound which is C1-C6 alkyl or a halogen atom which can be substituted with one or more halogen atoms.

[0135] [Mode 6] The compound N of the present application is G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d , and R 3a , R 3c , and R 3d are each a hydrogen atom, R 3b is a compound which is C1-C6 alkyl, C3-C7 cycloalkyl {the C1-C6 alkyl and the C3-C7 cycloalkyl can be substituted with one or more substituents selected from a halogen atom and a cyano group}, phenyl, pyridyl {the phenyl and the pyridyl can be substituted with one or more halogen atoms}, a halogen atom, or a hydrogen atom.

[0136] [Mode 7] The compound N of the present application is G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 CR 3d , and R 3a , R 3c , and R 3d are each a hydrogen atom, R 3b is a compound which is C1-C6 alkyl or a halogen atom which can be substituted with one or more halogen atoms.

[0137] [Mode 8] The compound according to Mode 1, wherein the combination of G 1 , G 2 , G 3 , and G 4 is as follows: G 1 CR 3a , G 2 CR 3b , G 3 CR 3c , G 4 is a combination of a nitrogen atom and CR 3d ; G 1 is a combination of a nitrogen atom, G 2 CR 3b , G 3 CR 3c , G 4 CR 3d ; G 1 CR3a 2 3 3c 4 3d 1 3a 2 3b 3 4 3d 3a 3c 3d 3b

[0138] [Mode 9] The compound according to Mode 2, wherein G 1 2 3 4 1 3a 2 3b 3 3c 4 3d 1 2 3b 3 3c 4 3d 1 3a 2 3 3c 4 3d 1 3a 2 3b 3 4 3d 3a 3c 3d 3b ​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​

[0139] [Mode 10] The compound according to Mode 1, wherein 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 are each a hydrogen atom, R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group can be substituted with 1 or more substituents selected from a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group can be substituted with 1 or more halogen atoms}, a halogen atom, or a hydrogen atom.

[0140] [Mode 11] The compound according to Mode 2, wherein 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 are each a hydrogen atom, R 3b is a C1-C6 alkyl group, a C3-C7 cycloalkyl group {the C1-C6 alkyl group and the C3-C7 cycloalkyl group can be substituted with 1 or more substituents selected from a halogen atom and a cyano group}, a phenyl group, a pyridyl group {the phenyl group and the pyridyl group can be substituted with 1 or more halogen atoms}, a halogen atom, or a hydrogen atom.

[0141] [Mode 12] The compound according to Mode 1, wherein 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 are each a hydrogen atom, R 3b is a C1-C6 alkyl group which can be substituted with 1 or more halogen atoms or a halogen atom.

[0142] [Mode 13] The compound according to Mode 2, wherein G 1 is CR3a G is CR 2 G is CR 3b G is CR 3 G is CR 3c G is CR 4 G is CR 3d R is a hydrogen atom, R 3a R is a hydrogen atom, R 3c R is a hydrogen atom, R 3d R is a hydrogen atom, R 3b R is a hydrogen atom, R

[0143] [Mode 14] The compound according to Mode 1, wherein G 1 G is CR 3a G is CR 2 G is CR 3b G is CR 3 G is CR 3c G is CR 4 G is CR 3d R is a hydrogen atom, R 3a R is a hydrogen atom, R 3c R is a hydrogen atom, R 3d R is a hydrogen atom, R 3b R is a hydrogen atom, R

[0144] [Mode 15] The compound according to Mode 2, wherein G 1 G is CR 3a G is CR 2 G is CR 3b G is CR 3 G is CR 3c G is CR 4 G is CR 3d R is a hydrogen atom, R 3a R is a hydrogen atom, R 3c R is a hydrogen atom, R 3d R is a hydrogen atom, R 3b R is a hydrogen atom, R

[0145] [Mode 16] The compound according to Mode 1, wherein G 1 G is CR 3a G is CR 2 G is CR 3b G is CR 3 G is CR3c , G 4 is CR 3d , R 3a , R 3c and R 3d are each a hydrogen atom, and R 3b is a C1-C6 alkyl group which can be substituted with one or more halogen atoms or a halogen atom.

[0146] [Mode 17] The compound according to Mode 2, wherein 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 each a hydrogen atom, and R 3b is a C1-C6 alkyl group which can be substituted with one or more halogen atoms or a halogen atom.

[0147] [Mode 18] The compound N according to the present application is a compound wherein Z is an oxygen atom, R 2 is a C1-C6 alkyl group.

[0148] [Mode 19] The compound N according to the present application is a compound wherein Z is an oxygen atom, R 2 is an ethyl group.

[0149] [Mode 20] The compound according to Mode 1, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0150] [Mode 21] The compound according to Mode 2, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0151] [Mode 22] The compound according to Mode 3, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0152] [Mode 23] The compound according to Mode 4, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0153] [Mode 24] The compound according to Mode 5, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0154] [Mode 25] The compound according to Mode 6, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0155] [Mode 26] The compound according to Mode 7, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0156] [Mode 27] The compound according to Mode 8, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0157] [Mode 28] The compound according to Mode 9, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0158] [Mode 29] The compound according to Mode 10, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0159] [Mode 30] The compound according to Mode 11, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0160] [Mode 31] The compound according to Mode 12, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0161] [Mode 32] The compound according to Mode 13, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0162] [Mode 33] The compound according to Mode 14, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0163] [Mode 34] The compound according to Mode 15, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0164] [Mode 35] The compound according to Mode 16, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0165] [Mode 36] The compound according to Mode 17, wherein Z is an oxygen atom, and R 2 is a C1-C6 alkyl group.

[0166] [Mode 37] The compound according to Mode 1, wherein Z is an oxygen atom, and R 2 is an ethyl group.

[0167] [Mode 38] The compound according to Mode 2, wherein Z is an oxygen atom, and R 2 is an ethyl group.

[0168] [Mode 39] The compound according to Mode 3, wherein Z is an oxygen atom, and R2 It is an ethyl group.

[0169] [Method 40] According to the compound of Method 4, where Z is an oxygen atom, R 2 It is an ethyl group.

[0170] [Method 41] According to the compound of Method 5, where Z is an oxygen atom, R 2 It is an ethyl group.

[0171] [Method 42] According to the compound of Method 6, where Z is an oxygen atom, R 2 It is an ethyl group.

[0172] [Method 43] According to the compound of Method 7, where Z is an oxygen atom, R 2 It is an ethyl group.

[0173] [Method 44] According to the compound of Method 8, where Z is an oxygen atom, R 2 It is an ethyl group.

[0174] [Method 45] According to the compound of Method 9, where Z is an oxygen atom, R 2 It is an ethyl group.

[0175] [Method 46] According to the compound of Method 10, where Z is an oxygen atom, R 2 It is an ethyl group.

[0176] [Method 47] According to the compound of Method 11, where Z is an oxygen atom, R 2 It is an ethyl group.

[0177] [Method 48] According to the compound of Method 12, where Z is an oxygen atom, R 2 It is an ethyl group.

[0178] [Method 49] According to the compound of Method 13, where Z is an oxygen atom, R 2 It is an ethyl group.

[0179] [Method 50] According to the compound of Method 14, where Z is an oxygen atom, R 2 It is an ethyl group.

[0180] [Method 51] According to the compound of Method 15, where Z is an oxygen atom, R 2 It is an ethyl group.

[0181] [Method 52] According to the compound of Method 16, where Z is an oxygen atom, R 2 It is an ethyl group.

[0182] [Method 53] According to the compound of Method 17, where Z is an oxygen atom, R 2 It is an ethyl group.

[0183] [Mode 54] The compound according to any one of Modes 1 to 53 or the compound N of the present application, wherein A 1 , A 2 , A 3 , A 4 , and A 5 are combined as follows: A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , A 5 is CR 4e ; A 1 is CR 4a , A 2 is CR 4b , A 3 is a nitrogen atom, A 4 is CR 4d , A 5 is CR 4e ; or A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is a nitrogen atom, R 4a is a hydrogen atom, R 4b , R 4c , and R 4d are the same or different and are C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl {the C1-C6 alkyl, the C1-C6 alkenyl, and the C3-C7 cycloalkyl can be substituted with 1 or more substituents selected from a halogen atom and a cyano group}, phenyl, pyridyl, pyrimidyl, pyrazolyl, triazolyl {the phenyl, the pyridyl, the pyrimidyl, the pyrazolyl, and the triazolyl can be substituted with 1 or more substituents selected from Group J}, OR 44 , S(O) q R 41 , a cyano group, a halogen atom, or a hydrogen atom, R 4e is C1-C6 alkyl, a halogen atom, or a hydrogen atom (wherein A 1 , A 2 , A 3 , A 4 , and A 5 are combinations other than A 1 , A 2A 3 A 4 and A 5 Combinations of CH respectively; A 1 A 2 A 3 and A 4 CH and A respectively 5 A combination of nitrogen atoms; A 1 A 2 A 3 and A 5 CH and A respectively 4 A combination of nitrogen atoms; and A 1 A 2 A 4 and A 5 CH and A respectively 3 (A combination of nitrogen atoms).

[0184] [Method 55] A compound according to any one of Methods 1 to 53 or Compound N of the present invention, wherein A 1 A 2 A 3 A 4 and A 5 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A 5 For CR 4e A combination; 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d A 5 For CR 4e A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 R is a combination of nitrogen atoms. 4a For hydrogen atoms, R 4b R 4c and R 4dthe same or different and are C1-C6alkyl which can be substituted with one or more halogen atoms, C1-C6alkoxy which can be substituted with one or more halogen atoms, C1-C6alkylthio which can be substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, R 4e is a halogen atom or a hydrogen atom (wherein A 1 , A 2 , A 3 , A 4 and A 5 combinations not including A 1 , A 2 , A 3 , A 4 and A 5 combinations in which A 1 , A 2 , A 3 and A 4 are each CH and A 5 is a nitrogen atom; A 1 , A 2 , A 3 and A 5 are each CH and A 4 is a nitrogen atom; and A 1 , A 2 , A 4 and A 5 are each CH and A 3 is a nitrogen atom).

[0185] [Mode 56] The compound according to any one of Modes 1 to 53 or the compound N of the present application, wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are C1-C6alkyl, C1-C6alkenyl, C3-C7cycloalkyl {the C1-C6alkyl, the C1-C6alkenyl and the C3-C7cycloalkyl can be substituted with one or more substituents selected from a halogen atom and a cyano group}, phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl {the phenyl, the pyridyl, the pyrimidinyl, the pyrazolyl and the triazolyl can be substituted with one or more substituents selected from Group J}, OR 44 , S(O)q R 41 , a cyano group, a halogen atom, or a hydrogen atom, R 4e is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (wherein A 1 , A 2 , A 3 , A 4 and A 5 combinations not including A 1 , A 2 , A 3 , A 4 and A 5 are combinations in which each of A 1 , A 2 , A 3 and A 5 is CH and A 4 is a nitrogen atom).

[0186] [Mode 57] The compound according to any one of Modes 1 to 53 or the compound N of the present application, wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is a nitrogen atom or CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group which can be substituted with one or more halogen atoms, a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C1-C6 alkylthio group which can be substituted with one or more halogen atoms, a cyano group, a halogen atom, or a hydrogen atom, R 4e is a halogen atom or a hydrogen atom (wherein A 1 , A 2 , A 3 , A 4 and A 5 combinations not including A 1 , A 2 , A 3 , A 4 and A 5 are combinations in which each of A 1 , A 2 , A 3 and A 5 is CH and A 4 is a nitrogen atom).

[0187] [Mode 58] The compound according to any one of Modes 1 to 53 or Compound N of the present application, wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4b , R 4c and R 4d are the same or different and are a C1-C6 alkyl group, a C1-C6 alkenyl group, a C3-C7 cycloalkyl group (which C1-C6 alkyl group, C1-C6 alkenyl group and C3-C7 cycloalkyl group can be substituted with 1 or more substituents selected from a halogen atom and a cyano group), a phenyl group, a pyridyl group, a pyrimidinyl group, a pyrazolyl group, a triazolyl group (which phenyl group, pyridyl group, pyrimidinyl group, pyrazolyl group and triazolyl group can be substituted with 1 or more substituents selected from Group J), OR 44 , S(O) q R 41 , a cyano group, a halogen atom or a hydrogen atom, R 4e is a C1-C6 alkyl group, a halogen atom or a hydrogen atom (where not all of R 4b , R 4c , R 4d and R 4e represent a hydrogen atom).

[0188] [Mode 59] The compound according to any one of Modes 1 to 53 or Compound N of the present application, wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4e is a C1-C6 alkyl group, a halogen atom or a hydrogen atom, R 4b , R 4c and R 4d are combined as follows:

[0189] R 4bC1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl {the C1-C6 alkyl, the C1-C6 alkenyl, and the C3-C7 cycloalkyl can be substituted with 1 or more substituents selected from a halogen atom and a cyano group}, phenyl, pyridyl, pyrimidyl, pyrazolyl, triazolyl {the phenyl, the pyridyl, the pyrimidyl, the pyrazolyl, and the triazolyl can be substituted with 1 or more substituents selected from Group J}, OR 44 , S(O) q R 41 , a cyano group, or a halogen atom, R 4c is a hydrogen atom, and R 4d and R 44 are the same or different and are C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl {the C1-C6 alkyl, the C1-C6 alkenyl, and the C3-C7 cycloalkyl can be substituted with 1 or more substituents selected from a halogen atom and a cyano group}, phenyl, pyridyl, pyrimidyl, pyrazolyl, triazolyl {the phenyl, the pyridyl, the pyrimidyl, the pyrazolyl, and the triazolyl can be substituted with 1 or more substituents selected from Group J}, OR q , S(O) 41 R 4b , a cyano group, a halogen atom, or a hydrogen atom, in combination; or

[0190] R 4c is a hydrogen atom, and R 44 is C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl {the C1-C6 alkyl, the C1-C6 alkenyl, and the C3-C7 cycloalkyl can be substituted with 1 or more substituents selected from a halogen atom and a cyano group}, phenyl, pyridyl, pyrimidyl, pyrazolyl, triazolyl {the phenyl, the pyridyl, the pyrimidyl, the pyrazolyl, and the triazolyl can be substituted with 1 or more substituents selected from Group J}, OR q , S(O) 41 R 4d , a cyano group, or a halogen atom, in combination.

[0191] [Mode 60] The compound according to any one of Modes 1 to 53 or the compound N of the present application, wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4b , R 4c , and R 4dthe same or different and are a combination of C1-C6 alkyl which can be substituted with one or more halogen atoms, C1-C6 alkoxy which can be substituted with one or more halogen atoms, C1-C6 alkylthio which can be substituted with one or more halogen atoms, cyano, a halogen atom or a hydrogen atom, R 4e is a halogen atom or a hydrogen atom (wherein, not R 4b , R 4c , R 4d and R 4e all represent a hydrogen atom).

[0192] [Mode 61] The compound according to any one of Modes 1 to 53 or Compound N of the present application, wherein A 1 is CR 4a , A 2 is CR 4b , A 3 is CR 4c , A 4 is CR 4d , A 5 is CR 4e , R 4a is a hydrogen atom, R 4e is a halogen atom or a hydrogen atom, R 4b , R 4c and R 4d are combined as follows:

[0193] R 4b is C1-C6 alkyl which can be substituted with one or more halogen atoms, C1-C6 alkoxy which can be substituted with one or more halogen atoms, C1-C6 alkylthio which can be substituted with one or more halogen atoms, cyano or a halogen atom, R 4c and R 4d are the same or different and are a combination of C1-C6 alkyl which can be substituted with one or more halogen atoms, C1-C6 alkoxy which can be substituted with one or more halogen atoms, C1-C6 alkylthio which can be substituted with one or more halogen atoms, cyano, a halogen atom or a hydrogen atom; or

[0194] R 4b is a hydrogen atom, R 4c is C1-C6 alkyl which can be substituted with one or more halogen atoms, C1-C6 alkoxy which can be substituted with one or more halogen atoms, C1-C6 alkylthio which can be substituted with one or more halogen atoms, cyano or a halogen atom, R 4d is a hydrogen atom.

[0195] [Mode 62] The compound according to any one of Modes 1 to 53 or Compound N of the present application, wherein A 1 is CR 4a , A2 CR 4b A 3 CR 4c A 4 CR 4d A 5 CR 4e R 4a is a hydrogen atom, R 4e is a halogen atom or a hydrogen atom, R 4b , R 4c and R 4d are combined as follows:

[0196] R 4b is a C1-C6 alkyl group which can be substituted with one or more halogen atoms, a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C1-C6 alkylthio group which can be substituted with one or more halogen atoms, a cyano group or a halogen atom, R 4c is a C1-C6 alkyl group which can be substituted with one or more halogen atoms, a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C1-C6 alkylthio group which can be substituted with one or more halogen atoms, a cyano group or a halogen atom, R 4d is a hydrogen atom;

[0197] R 4b is a C1-C6 alkyl group which can be substituted with one or more halogen atoms, a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C1-C6 alkylthio group which can be substituted with one or more halogen atoms, a cyano group or a halogen atom, R 4c is a hydrogen atom, R 4d is a C1-C6 alkyl group which can be substituted with one or more halogen atoms, a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C1-C6 alkylthio group which can be substituted with one or more halogen atoms, a cyano group or a halogen atom;

[0198] R 4b is a C1-C6 alkyl group which can be substituted with one or more halogen atoms, a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C1-C6 alkylthio group which can be substituted with one or more halogen atoms, a cyano group or a halogen atom, R 4c and R 4d are each a hydrogen atom; or

[0199] R 4b is a hydrogen atom, R 4c is a C1-C6 alkyl group which can be substituted with one or more halogen atoms, a C1-C6 alkoxy group which can be substituted with one or more halogen atoms, a C1-C6 alkylthio group which can be substituted with one or more halogen atoms, a cyano group or a halogen atom, R 4d is a hydrogen atom.

[0200] [Method 63] A compound according to any one of Methods 1 to 53 or Compound N of the present invention, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different C1-C6 alkoxy group, C1-C6 alkyl thio group or hydrogen atom that can be substituted by one or more halogen atoms, R 4e It is a halogen atom or a hydrogen atom (where, not R) 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0201] [Method 64] A compound according to any one of Methods 1 to 53 or Compound N of the present invention, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different C1-C6 alkoxy group, C1-C6 alkyl thio group or hydrogen atom that can be substituted by one or more halogen atoms, R 4e For hydrogen atoms (where, not R) 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0202] [Method A1] Compounds represented by formula (IA).

[0203]

[0204] [In the formula, R] 1AThis indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group W; a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from group U; a phenyl group that can be substituted by one or more substituents selected from group V; a five- or six-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group V; or a C(O)R group. 51 C(O)OR 51 Or C(O)NR 51 R 52 Other symbols represent the meanings defined in [1].

[0205] [Method A2] According to the compound of Method A1, wherein R 1A It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group W.

[0206] [Method A3] According to the compound of Method A1, wherein R 1A It is a C1-C6 alkyl group.

[0207] [Method A4] According to the compound of Method A1, wherein G 1 G 2 G 3 and G 4 The combinations are as follows: G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d Combinations; G 1 For nitrogen atoms, G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d Combinations; G 1 For CR 3a G 2 For nitrogen atoms, G 3 For CR 3c G 4 For CR 3d The combination; or G 1 For CR 3a G 2 For CR 3b G 3 For nitrogen atoms, G 4 For CR 3d The combination of R 3a R 3c and R 3dThey are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0208] [Method A5] According to the compound of Method A1, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl, a C3-C7 cycloalkyl (the C1-C6 alkyl and the C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), a phenyl, a pyridyl (the phenyl and the pyridyl may be substituted by one or more halogen atoms), a halogen atom, or a hydrogen atom.

[0209] [Method A6] According to the compound of Method A1, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0210] [Method A7] According to the compound of Method A1, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl, a C3-C7 cycloalkyl (the C1-C6 alkyl and the C3-C7 cycloalkyl can be substituted by one or more substituents selected from halogen atoms and cyano groups), a phenyl, a pyridyl (the phenyl and the pyridyl can be substituted by one or more halogen atoms), a halogen atom or a hydrogen atom.

[0211] [Method A8] According to the compound of Method A1, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0212] [Method A9] According to the compound of Method A2, wherein G 1 G 2 G 3 and G 4 The combinations are as follows: G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d Combinations; G 1 For nitrogen atoms, G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d Combinations; G 1 For CR 3a G 2 For nitrogen atoms, G 3 For CR 3c G 4 For CR 3d The combination; or G 1 For CR 3a G 2 For CR 3b G 3 For nitrogen atoms, G 4 For CR 3d The combination of R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0213] [Method A10] According to the compound of method A3, wherein G1 G 2 G 3 and G 4 The combinations are as follows: G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d Combinations; G 1 For nitrogen atoms, G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d Combinations; G 1 For CR 3a G 2 For nitrogen atoms, G 3 For CR 3c G 4 For CR 3d The combination; or G 1 For CR 3a G 2 For CR 3b G 3 For nitrogen atoms, G 4 For CR 3d The combination of R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0214] [Method A11] According to the compound of method A2, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl, a C3-C7 cycloalkyl (the C1-C6 alkyl and the C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), a phenyl, a pyridyl (the phenyl and the pyridyl may be substituted by one or more halogen atoms), a halogen atom, or a hydrogen atom.

[0215] [Method A12] According to the compound of method A3, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl, a C3-C7 cycloalkyl (the C1-C6 alkyl and the C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), a phenyl, a pyridyl (the phenyl and the pyridyl may be substituted by one or more halogen atoms), a halogen atom, or a hydrogen atom.

[0216] [Method A13] According to the compound of method A2, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0217] [Method A14] According to the compound of method A3, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0218] [Method A15] According to the compound of method A2, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl, a C3-C7 cycloalkyl (the C1-C6 alkyl and the C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), a phenyl, a pyridyl (the phenyl and the pyridyl may be substituted by one or more halogen atoms), a halogen atom, or a hydrogen atom.

[0219] [Method A16] According to the compound of method A3, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl, a C3-C7 cycloalkyl (the C1-C6 alkyl and the C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), a phenyl, a pyridyl (the phenyl and the pyridyl may be substituted by one or more halogen atoms), a halogen atom, or a hydrogen atom.

[0220] [Method A17] According to the compound of Method A2, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0221] [Method A18] According to the compound of Method A3, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R3d They are hydrogen atoms, R 3b It is a C1-C6 alkyl or halogen atom that can be replaced by one or more halogen atoms.

[0222] [Method A19] According to Method A1, the compound, where Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0223] [Method A20] According to the compound of Method A1, where Z is an oxygen atom, R 2 It is an ethyl group.

[0224] [Method A21] The compound according to Method A2, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0225] [Method A22] The compound according to Method A3, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0226] [Method A23] According to the compound of Method A4, where Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0227] [Method A24] The compound according to Method A5, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0228] [Method A25] The compound according to Method A6, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0229] [Method A26] The compound according to Method A7, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0230] [Method A27] According to the compound of Method A8, where Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0231] [Method A28] The compound according to Method A9, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0232] [Method A29] According to the compound of Method A10, where Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0233] [Method A30] The compound according to Method A11, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0234] [Method A31] The compound according to Method A12, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0235] [Method A32] The compound according to Method A13, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0236] [Method A33] The compound according to Method A14, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0237] [Method A34] The compound according to Method A15, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0238] [Method A35] The compound according to Method A16, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0239] [Method A36] The compound according to Method A17, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0240] [Method A37] The compound according to Method A18, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0241] [Method A38] The compound according to Method A2, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0242] [Method A39] According to Method A3, the compound is a carbon atom, where Z is an oxygen atom, R 2 It is an ethyl group.

[0243] [Method A40] According to Method A4, the compound is a carbon atom, where Z is an oxygen atom, R 2 It is an ethyl group.

[0244] [Method A41] According to the compound of Method A5, where Z is an oxygen atom, R 2 It is an ethyl group.

[0245] [Method A42] According to the compound of Method A6, where Z is an oxygen atom, R 2 It is an ethyl group.

[0246] [Method A43] According to the compound of Method A7, where Z is an oxygen atom, R 2 It is an ethyl group.

[0247] [Method A44] According to the compound of Method A8, where Z is an oxygen atom, R2 It is an ethyl group.

[0248] [Method A45] The compound according to Method A9, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0249] [Method A46] The compound according to Method A10, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0250] [Method A47] According to the compound of Method A11, where Z is an oxygen atom, R 2 It is an ethyl group.

[0251] [Method A48] The compound according to Method A12, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0252] [Method A49] The compound according to Method A13, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0253] [Method A50] The compound according to Method A14, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0254] [Method A51] The compound according to Method A15, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0255] [Method A52] The compound according to Method A16, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0256] [Method A53] The compound according to Method A17, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0257] [Method A54] The compound according to Method A18, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0258] [Method A55] A compound according to any one of methods A1 to A54, wherein A 1 A 2 A 3 A 4 and A 5 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A5 For CR 4e A combination; 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d A 5 For CR 4e A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 R is a combination of nitrogen atoms. 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano, halogen atom or hydrogen atom, R 4e It is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (where A is C1-C6 alkyl group, halogen atom, or hydrogen atom). 1 A 2 A 3 A 4 and A 5 The combination does not include A 1 A 2 A 3 A 4 and A 5 Combinations of CH respectively; A 1 A 2 A 3 and A 4 CH and A respectively 5 A combination of nitrogen atoms; A 1 A 2 A 3 and A 5 CH and A respectively 4 A combination of nitrogen atoms; and A 1 A 2A 4 and A 5 CH and A respectively 3 (A combination of nitrogen atoms).

[0259] [Method A56] A compound according to any one of methods A1 to A54, wherein A 1 A 2 A 3 A 4 and A 5 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A 5 For CR 4e A combination; 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d A 5 For CR 4e A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 R is a combination of nitrogen atoms. 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 4e It is a halogen atom or a hydrogen atom (where A is a halogen atom or a hydrogen atom). 1 A 2 A 3 A 4 and A 5 The combination does not include A 1 A 2 A 3 A 4 and A 5 Combinations of CH respectively; A1 A 2 A 3 and A 4 CH and A respectively 5 A combination of nitrogen atoms; A 1 A 2 A 3 and A 5 CH and A respectively 4 A combination of nitrogen atoms; and A 1 A 2 A 4 and A 5 CH and A respectively 3 (A combination of nitrogen atoms).

[0260] [Method A57] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano, halogen atom, or hydrogen atom, R 4e It is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (where A is C1-C6 alkyl group, halogen atom, or hydrogen atom). 1 A 2 A 3 A 4 and A 5 The combination does not include A 1 A 2 A 3 A 4 and A 5 These are combinations of CH; and A. 1 A 2 A 3 and A5 CH and A respectively 4 (A combination of nitrogen atoms).

[0261] [Method A58] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 4e It is a halogen atom or a hydrogen atom (where A is a halogen atom or a hydrogen atom). 1 A 2 A 3 A 4 and A 5 The combination does not include A 1 A 2 A 3 A 4 and A 5 These are combinations of CH; and A. 1 A 2 A 3 and A 5 CH and A respectively 4 (A combination of nitrogen atoms).

[0262] [Method A59] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4dThe same or different and being C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano, halogen atom, or hydrogen atom, R 4e It is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (wherein, not R). 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0263] [Method A60] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4e R is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom. 4b R 4c and R 4d The combinations are as follows:

[0264] R 4b The following are not directly related to the preceding text: C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano or halogen atom, R 4c and R 4dThe same or different and being C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 A combination of cyano, halogen, or hydrogen atoms; or

[0265] R 4b For hydrogen atoms, R 4c The following are not directly related to the preceding text: C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano or halogen atom, R 4d It is a combination of hydrogen atoms.

[0266] [Method A61] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 4e It is a halogen atom or a hydrogen atom (where, not R) 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0267] [Method A62] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4e R is a halogen atom or a hydrogen atom. 4b R 4c and R 4d The combinations are as follows:

[0268] R 4b R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4c and R 4d The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, or a combination of C1-C6 alkyl thio, cyano, halogen atom, or hydrogen atom that can be substituted with one or more halogen atoms; or

[0269] R 4b For hydrogen atoms, R 4c R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4d It is a combination of hydrogen atoms.

[0270] [Method A63] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4e R is a halogen atom or a hydrogen atom. 4b R 4c and R 4d The combinations are as follows:

[0271] R 4b R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4c R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4d It is a combination of hydrogen atoms;

[0272] R 4b R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4c For hydrogen atoms, R 4d It can be a C1-C6 alkyl 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 C1-C6 alkyl thio group, a cyano group, or a combination of halogen atoms that can be substituted by one or more halogen atoms;

[0273] R 4b R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4c and R 4d Each is a combination of hydrogen atoms; or

[0274] R 4b For hydrogen atoms, R 4c R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4d It is a combination of hydrogen atoms.

[0275] [Method A64] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4aFor hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group that can be substituted with one or more halogen atoms, or a hydrogen atom, R 4e It is a halogen atom or a hydrogen atom (where, not R) 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0276] [Method A65] A compound according to any one of methods A1 to A54, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group that can be substituted with one or more halogen atoms, or a hydrogen atom, R 4e For hydrogen atoms (where, not R) 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0277] Compounds represented by formula (IB) [method B1].

[0278]

[0279] [In the formula, the symbols represent the meanings defined in [2].]

[0280] [Method B2] According to the compound of method B1, wherein R 41 and R 42 The same or different C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by more than one halogen atom, R 45 It is a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more substituents selected from group X.

[0281] [Method B3] According to the compound of method B1, wherein R 41 R 42 and R45 They may be the same or different and are C1-C6 alkyl or hydrogen atoms.

[0282] [Method B4] According to the compound of method B1, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0283] [Method B5] According to the compound of method B1, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0284] [Method B6] According to the compound of method B1, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0285] [Method B7] According to the compound of method B1, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3aR 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0286] [Method B8] According to the compound of method B2, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0287] [Method B9] According to the compound of method B3, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0288] [Method B10] According to the compound of method B2, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0289] [Method B11] According to the compound of method B3, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0290] [Method B12] According to the compound of method B2, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0291] [Method B13] According to the compound of method B3, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0292] [Method B14] According to the compound of method B2, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0293] [Method B15] According to the compound of method B3, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0294] [Method B16] A compound according to Method B1, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0295] [Method B17] According to Method B1, the compound is wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0296] [Method B18] The compound according to Method B2, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0297] [Method B19] The compound according to Method B3, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0298] [Method B20] The compound according to Method B4, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0299] [Method B21] The compound according to Method B5, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0300] [Method B22] The compound according to Method B6, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0301] [Method B23] The compound according to Method B7, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0302] [Method B24] The compound according to Method B8, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0303] [Method B25] The compound according to Method B9, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0304] [Method B26] The compound according to Method B10, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0305] [Method B27] The compound according to Method B11, wherein Z is an oxygen atom, R2 It is a C1-C6 alkyl group.

[0306] [Method B28] The compound according to Method B12, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0307] [Method B29] The compound according to Method B13, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0308] [Method B30] The compound according to Method B14, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0309] [Method B31] The compound according to Method B15, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0310] [Method B32] A compound according to Method B2, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0311] [Method B33] According to Method B3, in which Z is an oxygen atom, R 2 It is an ethyl group.

[0312] [Method B34] A compound according to Method B4, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0313] [Method B35] A compound according to Method B5, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0314] [Method B36] A compound according to Method B6, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0315] [Method B37] A compound according to Method B7, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0316] [Method B38] A compound according to Method B8, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0317] [Method B39] According to Method B9, in which Z is an oxygen atom, R 2 It is an ethyl group.

[0318] [Method B40] A compound according to Method B10, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0319] [Method B41] A compound according to Method B11, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0320] [Method B42] The compound according to Method B12, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0321] [Method B43] The compound according to Method B13, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0322] [Method B44] A compound according to Method B14, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0323] [Method B45] A compound according to Method B15, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0324] [Method B46] A compound according to any one of Methods B1 to B45, wherein A 1 A 2 A 3 and A 4 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A combination; 1 For CR 4a A 2 For nitrogen atoms, A 3 For CR 4c A 4 For CR 4d A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d The combination of R 4a and R 4d They are hydrogen atoms, R 4b and R 4c The same or different and can be substituted by one or more substituents selected from group X, OR 44 halogen atoms or hydrogen atoms (where A 1 A 2 A 3 and A4 The combination does not include A 1 A 2 A 3 and A 4 They are combinations of CH respectively;

[0325] A 1 A 2 and A 3 CH and A respectively 4 A combination of nitrogen atoms; A 1 A 2 and A 4 CH and A respectively 3 A combination of nitrogen atoms; and A 1 A 3 and A 4 CH and A respectively 2 (A combination of nitrogen atoms).

[0326] [Method B47] A compound according to any one of Methods B1 to B45, wherein A 1 A 2 A 3 and A 4 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A combination; 1 For CR 4a A 2 For nitrogen atoms, A 3 For CR 4c A 4 For CR 4d A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d The combination of R 4a and R 4d They are hydrogen atoms, R 4b and R 4c The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, or a hydrogen atom (where A is the same or different). 1 A 2 A 3 and A 4The combination does not include A 1 A 2 A 3 and A 4 Combinations of CH respectively; A 1 A 2 and A 3 CH and A respectively 4 A combination of nitrogen atoms; A 1 A 2 and A 4 CH and A respectively 3 A combination of nitrogen atoms; and A 1 A 3 and A 4 CH and A respectively 2 (A combination of nitrogen atoms).

[0327] [Method B48] A compound according to any one of Methods B1 to B45, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d R 4a and R 4d They are hydrogen atoms, R 4b and R 4c The same or different and can be substituted by one or more substituents selected from group X, OR 44 halogen atoms or hydrogen atoms (where R 4b and R 4c (They do not both represent hydrogen atoms).

[0328] [Method B49] A compound according to any one of Methods B1 to B45, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d R 4a and R 4d They are hydrogen atoms, R 4b and R 4c The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, or a hydrogen atom (wherein, R 4b and R 4c (They do not both represent hydrogen atoms).

[0329] Compounds represented by formula (IB) [method B50].

[0330]

[0331] [In the formula, the symbols represent the meanings defined in [1].]

[0332] [Method B51] According to the compound of method B50, wherein R 41 and R 42 The same or different C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by more than one halogen atom, R 45 It is a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more substituents selected from group X.

[0333] [Method B52] According to the compound of method B50, wherein R 41 R 42 and R 45 They may be the same or different and are C1-C6 alkyl or hydrogen atoms.

[0334] [Method B53] According to the compound of method B50, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0335] [Method B54] According to the compound of method B50, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0336] [Method B55] According to the compound of method B50, wherein G 1 For CR 3aG 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0337] [Method B56] According to the compound of method B50, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0338] [Method B57] According to the compound of method B51, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0339] [Method B58] The compound according to Method B52, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0340] [Method B59] According to the compound of method B51, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0341] [Method B60] According to the compound of method B52, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0342] [Method B61] According to the compound of method B51, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0343] [Method B62] According to the compound of method B52, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3bIt can be a C1-C6 alkyl group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms.

[0344] [Method B63] According to the compound of method B51, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0345] [Method B64] According to the compound of method B52, wherein G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b It is a halogen atom.

[0346] [Method B65] The compound according to Method B50, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0347] [Method B66] The compound according to Method B50, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0348] [Method B67] The compound according to Method B51, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0349] [Method B68] The compound according to Method B52, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0350] [Method B69] The compound according to Method B53, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0351] [Method B70] The compound according to Method B54, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0352] [Method B71] The compound according to Method B55, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0353] [Method B72] The compound according to Method B56, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0354] [Method B73] The compound according to Method B57, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0355] [Method B74] The compound according to Method B58, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0356] [Method B75] The compound according to Method B59, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0357] [Method B76] The compound according to Method B60, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0358] [Method B77] The compound according to Method B61, wherein Z is an oxygen atom, R 2 Compounds that are C1-C6 alkyl groups.

[0359] [Method B78] The compound according to Method B62, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0360] [Method B79] The compound according to Method B63, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0361] [Method B80] The compound according to Method B64, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0362] [Method B81] The compound according to Method B51, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0363] [Method B82] The compound according to Method B52, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0364] [Method B83] The compound according to Method B53, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0365] [Method B84] The compound according to Method B54, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0366] [Method B85] The compound according to Method B55, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0367] [Method B86] The compound according to Method B56, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0368] [Method B87] The compound according to Method B57, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0369] [Method B88] The compound according to Method B58, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0370] [Method B89] The compound according to Method B59, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0371] [Method B90] The compound according to Method B60, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0372] [Method B91] The compound according to Method B61, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0373] [Method B92] The compound according to Method B62, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0374] [Method B93] The compound according to Method B63, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0375] [Method B94] The compound according to Method B64, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0376] [Method B95] A compound according to any one of methods B50 to B94, wherein A 1 A 2 A 3 and A 4 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4Nitrogen atom or CR 4d A combination; 1 For CR 4a A 2 For nitrogen atoms, A 3 For CR 4c A 4 For CR 4d A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d The combination of R 4a and R 4d They are hydrogen atoms, R 4b and R 4c The same or different and can be substituted by one or more substituents selected from group X, OR 44 halogen atoms or hydrogen atoms (where A 1 A 2 A 3 and A 4 The combination does not include A 1 A 2 A 3 and A 4 Combinations of CH respectively; A 1 A 2 and A 3 CH and A respectively 4 A combination of nitrogen atoms; A 1 A 2 and A 4 CH and A respectively 3 A combination of nitrogen atoms; and A 1 A 3 and A 4 CH and A respectively 2 (A combination of nitrogen atoms).

[0377] [Method B96] A compound according to any one of methods B50 to B94, wherein A 1 A 2 A 3 and A 4 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A combination;1 For CR 4a A 2 For nitrogen atoms, A 3 For CR 4c A 4 For CR 4d A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d The combination of R 4a and R 4d They are hydrogen atoms, R 4b and R 4c The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, or a hydrogen atom (where A is the same or different). 1 A 2 A 3 and A 4 The combination does not include A 1 A 2 A 3 and A 4 Combinations of CH respectively; A 1 A 2 and A 3 CH and A respectively 4 A combination of nitrogen atoms; A 1 A 2 and A 4 CH and A respectively 3 A combination of nitrogen atoms; and A 1 A 3 and A 4 CH and A respectively 2 (A combination of nitrogen atoms).

[0378] [Method B97] A compound according to any one of methods B50 to B94, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d R 4a and R 4d They are hydrogen atoms, R 4b and R 4c The same or different and can be substituted by one or more substituents selected from group X, OR 44halogen atoms or hydrogen atoms (where R 4b and R 4c (They do not both represent hydrogen atoms).

[0379] [Method B98] A compound according to any one of methods B50 to B94, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d R 4a and R 4d They are hydrogen atoms, R 4b and R 4c The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, or a hydrogen atom (wherein, R 4b and R 4c (They do not both represent hydrogen atoms).

[0380] The following compounds can be cited as examples of compounds represented by formula (II) (hereinafter also referred to as intermediate C).

[0381] [Method C1] Intermediate C is G 1 G 2 G 3 and G 4 The combinations are as follows: G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d Combinations; G 1 For nitrogen atoms, G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d Combinations; G 1 For CR 3a G 2 For nitrogen atoms, G 3 For CR 3c G 4 For CR 3d The combination; or G 1 For CR 3a G 2 For CR 3b G3 For nitrogen atoms, G 4 For CR 3d The combination of R 3a R 3c and R 3d They are hydrogen atoms, R 3b A compound consisting of C1-C6 alkyl or halogen atoms that can be replaced by one or more halogen atoms.

[0382] [Method C2] Intermediate C is G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b Compounds of C1-C6 alkyl, C3-C7 cycloalkyl (the C1-C6 alkyl and the C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl (the phenyl and the pyridyl may be substituted by one or more halogen atoms), halogen atoms, or hydrogen atoms.

[0383] [Method C3] Intermediate C is G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 Nitrogen atom or CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3b A compound consisting of C1-C6 alkyl or halogen atoms that can be replaced by one or more halogen atoms.

[0384] [Method C4] Intermediate C is G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms, R 3bCompounds of C1-C6 alkyl, C3-C7 cycloalkyl (the C1-C6 alkyl and the C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl (the phenyl and the pyridyl may be substituted by one or more halogen atoms), halogen atoms, or hydrogen atoms.

[0385] [Method C5] Intermediate C is G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d R 3a R 3c and R 3d They are hydrogen atoms and R 3b A compound consisting of C1-C6 alkyl or halogen atoms that can be replaced by one or more halogen atoms.

[0386] [Method C6] Intermediate C is Z for oxygen atom, R 2 Compounds that are C1-C6 alkyl groups.

[0387] [Method C7] Intermediate C is Z for oxygen atom, R 2 It is a compound of ethyl group.

[0388] [Method C8] The compound according to Method C1, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0389] [Method C9] The compound according to Method C2, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0390] [Method C10] The compound according to Method C3, wherein Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0391] [Method C11] According to the compound of method C4, where Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0392] [Method C12] According to the compound of method C5, where Z is an oxygen atom, R 2 It is a C1-C6 alkyl group.

[0393] [Method C13] According to Method C1, the compound, where Z is an oxygen atom, R 2 It is an ethyl group.

[0394] [Method C14] The compound according to Method C2, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0395] [Method C15] The compound according to Method C3, wherein Z is an oxygen atom, R 2 It is an ethyl group.

[0396] [Method C16] According to the compound of method C4, where Z is an oxygen atom, R 2 It is an ethyl group.

[0397] [Method C17] According to the compound of method C5, where Z is an oxygen atom, R 2 It is an ethyl group.

[0398] [Method C18] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 A 2 A 3 A 4 and A 5 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A 5 For CR 4e A combination; 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d A 5 For CR 4e A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 R is a combination of nitrogen atoms. 4a For hydrogen atoms, R 4b R 4c and R 4dThe same or different and being C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano, halogen atom, or hydrogen atom, R 4e It is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (where A is C1-C6 alkyl group, halogen atom, or hydrogen atom). 1 A 2 A 3 A 4 and A 5 The combination does not include A 1 A 2 A 3 A 4 and A 5 Combinations of CH respectively; A 1 A 2 A 3 and A 4 CH and A respectively 5 A combination of nitrogen atoms; A 1 A 2 A 3 and A 5 CH and A respectively 4 A combination of nitrogen atoms; and A 1 A 2 A 4 and A 5 CH and A respectively 3 (A combination of nitrogen atoms).

[0399] [Method C19] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 A 2 A 3 A 4 and A 5 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A 5 For CR 4e A combination; 1 For CR4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d A 5 For CR 4e A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 R is a combination of nitrogen atoms. 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 4e It is a halogen atom or a hydrogen atom (where A is a halogen atom or a hydrogen atom). 1 A 2 A 3 A 4 and A 5 The combination does not include A 1 A 2 A 3 A 4 and A 5 Combinations of CH respectively; A 1 A 2 A 3 and A 4 CH and A respectively 5 A combination of nitrogen atoms; A 1 A 2 A 3 and A 5 CH and A respectively 4 A combination of nitrogen atoms; and A 1 A 2 A 4 and A 5 CH and A respectively 3 (A combination of nitrogen atoms).

[0400] [Formula C20] A compound according to any one of Formulas C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano, halogen atom, or hydrogen atom, R 4e It is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (where A is C1-C6 alkyl group, halogen atom, or hydrogen atom). 1 A 2 A 3 A 4 and A 5 The combination does not include A 1 A 2 A 3 A 4 and A 5 These are combinations of CH; and A. 1 A 2 A 3 and A 5 CH and A respectively 4 (A combination of nitrogen atoms).

[0401] [Method C21] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 Nitrogen atom or CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4dThe same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 4e It is a halogen atom or a hydrogen atom (where A is a halogen atom or a hydrogen atom). 1 A 2 A 3 A 4 and A 5 The combination does not include A 1 A 2 A 3 A 4 and A 5 These are combinations of CH; and A. 1 A 2 A 3 and A 5 CH and A respectively 4 (A combination of nitrogen atoms).

[0402] [Method C22] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano, halogen atom, or hydrogen atom, R 4e It is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom (wherein, not R). 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0403] [Method C23] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4e R is a C1-C6 alkyl group, a halogen atom, or a hydrogen atom. 4b R 4c and R 4d The combinations are as follows:

[0404] R 4b The following are not directly related to the preceding text: C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 , cyano, or halogen atom, R 4c and R 4d The same or different and being C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O) q R 41 A combination of cyano, halogen, or hydrogen atoms; or

[0405] R 4b For hydrogen atoms, R 4c The following are not directly related to the preceding text: C1-C6 alkyl, C1-C6 alkenyl, C3-C7 cycloalkyl (the C1-C6 alkyl, C1-C6 alkenyl, and C3-C7 cycloalkyl may be substituted by one or more substituents selected from halogen atoms and cyano groups), phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl (the phenyl, pyridyl, pyrimidinyl, pyrazolyl, and triazolyl may be substituted by one or more substituents selected from group J), OR 44 S(O)q R 41 , cyano, or halogen atom, R 4d It is a combination of hydrogen atoms.

[0406] [Method C24] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 4e It is a halogen atom or a hydrogen atom (where, not R) 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0407] [Method C25] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4e R is a halogen atom or a hydrogen atom. 4b R 4c and R 4d The combinations are as follows:

[0408] R 4b R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4c and R 4dThe same or different and being a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, or a combination of C1-C6 alkyl thio, cyano, halogen atom, or hydrogen atom that can be substituted with one or more halogen atoms; or

[0409] R 4b For hydrogen atoms, R 4c R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4d It is a combination of hydrogen atoms.

[0410] [Method C26] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4e R is a halogen atom or a hydrogen atom. 4b R 4c and R 4d The combinations are as follows:

[0411] R 4b R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4c R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4d It is a combination of hydrogen atoms;

[0412] R 4b R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4c For hydrogen atoms, R 4dIt can be a C1-C6 alkyl 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 C1-C6 alkyl thio group, a cyano group, or a combination of halogen atoms that can be substituted by one or more halogen atoms;

[0413] R 4b R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4c and R 4d Each is a combination of hydrogen atoms; or

[0414] R 4b For hydrogen atoms, R 4c R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group, a cyano group, or a halogen atom that can be substituted with one or more halogen atoms. 4d It is a combination of hydrogen atoms.

[0415] [Method C27] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group that can be substituted with one or more halogen atoms, or a hydrogen atom, R 4e It is a halogen atom or a hydrogen atom (where, not R) 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0416] [Method C28] A compound according to any one of methods C1 to C17 or intermediate C, wherein A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A4 For CR 4d A 5 For CR 4e R 4a For hydrogen atoms, R 4b R 4c and R 4d The same or different and being a C1-C6 alkoxy group that can be substituted with one or more halogen atoms, a C1-C6 alkyl thio group that can be substituted with one or more halogen atoms, or a hydrogen atom, R 4e For hydrogen atoms (where, not R) 4b R 4c R 4d and R 4e (All represent hydrogen atoms).

[0417] Next, the method for manufacturing compound X of the present invention will be described.

[0418] Manufacturing Method 1

[0419] The compound represented by formula (I-b) (hereinafter referred to as compound (I-b)) or the compound represented by formula (I-c) (hereinafter referred to as compound (I-c)) can be prepared by reacting the compound represented by formula (I-a) (hereinafter referred to as compound (I-a)) with an oxidizing agent.

[0420]

[0421] [In the formula, the symbols represent the same meaning as above.]

[0422] First, the method for producing compound (I-b) from compound (I-a) is described.

[0423] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include, for example, halogenated hydrocarbons such as dichloromethane and chloroform; nitriles such as acetonitrile; alcohols such as methanol and ethanol; acetic acid; water; and mixtures of two or more of them.

[0424] Examples of oxidizing agents used in the reaction include sodium periodate, m-chloroperoxybenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide.

[0425] When using hydrogen peroxide as an oxidant, an alkali or catalyst can be added as needed.

[0426] Sodium carbonate is an example of a base used in the reaction. When a base is used in the reaction, it is usually used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (I-a).

[0427] Examples of catalysts used in the reaction include tungstate and sodium tungstate. When a catalyst is used in the reaction, it is typically used in a ratio of 0.01 to 0.5 moles relative to 1 mole of compound (I-a).

[0428] In the reaction, the oxidant is usually used in a ratio of 1 to 1.2 moles relative to 1 mole of compound (I-a).

[0429] The reaction temperature is typically in the range of -20 to 80°C. The reaction time is typically in the range of 0.1 to 12 hours.

[0430] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. The organic layer is then washed, as needed, with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of an alkali (e.g., sodium bicarbonate). The organic layer is dried and concentrated to obtain compound (I-b).

[0431] Next, the method for producing compound (I-c) from compound (I-b) will be described.

[0432] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of them.

[0433] Examples of oxidizing agents used in the reaction include mCPBA and hydrogen peroxide.

[0434] When using hydrogen peroxide as an oxidant, an alkali or catalyst can be added as needed.

[0435] Sodium carbonate is an example of a base used in the reaction. When a base is used in the reaction, it is usually used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (I-b).

[0436] Sodium tungstate can be cited as an example of a catalyst used in the reaction. When a catalyst is used in the reaction, it is usually used in a ratio of 0.01 to 0.5 moles relative to 1 mole of compound (I-b).

[0437] In the reaction, the oxidant is usually used in a ratio of 1 to 2 moles relative to 1 mole of compound (I-b).

[0438] The reaction temperature is typically in the range of -20 to 120°C. The reaction time is typically in the range of 0.1 to 12 hours.

[0439] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. The organic layer is then washed, as needed, with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of an alkali (e.g., sodium bicarbonate). The organic layer is then dried and concentrated to obtain compound (I-c).

[0440] Alternatively, compound (I-c) can also be produced by reacting compound (I-a) with an oxidizing agent using a one-step reaction (one-pot process).

[0441] The reaction can be carried out using an oxidizing agent in a ratio of 2 to 5 moles relative to 1 mole of compound (I-a), following the method for producing compound (I-c) from compound (I-b).

[0442] Manufacturing Method 2

[0443] The compound represented by formula (I-1-A) (hereinafter referred to as compound (I-1-A)) can be prepared by reacting the compound represented by formula (M1-1-A) (hereinafter referred to as compound (M1-1-A)) with the compound represented by formula (M2-1) (hereinafter referred to as compound (M2-1)) in the presence of a condensing agent.

[0444]

[0445] [In the formula, R] A [The symbols represent C1-C6 chain hydrocarbon groups that can be substituted by one or more substituents selected from group W; C3-C7 cycloalkyl groups that can be substituted by one or more substituents selected from group U; phenyl groups that can be substituted by one or more substituents selected from group V; and five- or six-membered aromatic heterocyclic groups that can be substituted by one or more substituents selected from group V. Other symbols have the same meaning as above.]

[0446] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers such as tetrahydrofuran (hereinafter referred to as THF) and methyl tert-butyl ether (hereinafter referred to as MTBE); halogenated hydrocarbons; aromatic hydrocarbons such as toluene and xylene; esters such as ethyl acetate and butyl acetate; nitriles; aprotic polar solvents such as N-methylpyrrolidone (hereinafter referred to as NMP), N,N-dimethylformamide (hereinafter referred to as DMF), and dimethyl sulfoxide (hereinafter referred to as DMSO); nitrogen-containing aromatic compounds such as pyridine, methylpyridine, dimethylpyridine, and quinoline, and mixtures of two or more of them.

[0447] Examples of condensing agents used in the reaction include 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide, among other carbodiimides.

[0448] A catalyst may be used in the reaction as needed. Examples of catalysts used in the reaction include 1-hydroxybenzotriazole. When a catalyst is used in the reaction, it is typically used in a ratio of 0.01 to 0.5 moles relative to 1 mole of compound (M1-1-A).

[0449] In the reaction, a base may be used as needed. Examples of organic bases used in the reaction include triethylamine, N,N-diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine (hereinafter referred to as organic bases). When using a base in the reaction, the base is usually used in a ratio of 1 to 2 moles relative to 1 mole of compound (M1-1-A).

[0450] In the reaction, relative to 1 mole of compound (M1-1-A), compound (M2-1) is usually used in a ratio of 1 to 2 moles, and the condensing agent is usually used in a ratio of 1 to 2 moles.

[0451] The reaction temperature is typically in the range of 0–200°C. The reaction time is typically in the range of 0.1–12 hours.

[0452] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (I-1-A).

[0453] Compound (M2-1) is a commercially available compound or can be manufactured using known methods.

[0454] Manufacturing Method 3

[0455] Compound (I-1-A) can also be produced by reacting compound (M1-1-A) with a compound represented by formula (M2-2) (hereinafter referred to as compound (M2-2)).

[0456]

[0457] [In the formula, the symbols represent the same meaning as above.]

[0458] The reaction is usually carried out in a solvent. Examples of solvents 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 and mixtures of two or more of them.

[0459] Bases can be used in reactions as needed. Examples of bases used in reactions include alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter referred to as alkali metal hydroxides); and organic bases. When using a base in a reaction, the base is usually used in a ratio of 1 to 2 moles relative to 1 mole of compound (M1-1-A).

[0460] In the reaction, compound (M2-2) is usually used in a ratio of 0.8 to 1.2 moles relative to 1 mole of compound (M1-1-A).

[0461] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 24 hours.

[0462] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (I-1-A).

[0463] The compound (M2-2) is a commercially available compound or can be manufactured using known methods.

[0464] Manufacturing Method 4

[0465] The compound represented by formula (I-2-B) (hereinafter referred to as compound (I-2-B)) can be prepared by reacting the compound represented by formula (II) (hereinafter referred to as compound (II)) with the compound represented by formula (R-1) (hereinafter referred to as compound (R-1)) in the presence of a base.

[0466]

[0467] [In the formula, R] B This refers to C1-C6 chain hydrocarbon groups that can be substituted by one or more substituents selected from group W, C3-C7 cycloalkyl groups that can be substituted by one or more substituents selected from group U, and C(O)R. 51 C(O)OR 51 、or C(O)NR 51 R 52 L represents a leaving group such as a chlorine atom or a bromine atom; other symbols have the same meaning as above.

[0468] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[0469] Examples of bases used in reactions include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides), alkali metal carbonates, and organic bases.

[0470] In the reaction, relative to 1 mole of compound (II), compound (R-1) 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.

[0471] The reaction temperature is typically in the range of 0–100°C. The reaction time is typically in the range of 0.1–24 hours.

[0472] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (I-2-B).

[0473] Compound (R-1) is a commercially available compound or can be manufactured using known methods.

[0474] Manufacturing Method 5

[0475] The compound represented by formula (I-1) (hereinafter referred to as compound (I-1)) can be produced by reacting the compound represented by formula (M1-2) (hereinafter referred to as compound (M1-2)) with the compound represented by formula (M2-3) (hereinafter referred to as compound (M2-3)).

[0476]

[0477] [In the formula, V] 1 [This symbol represents a halogen atom; other symbols have the same meaning as described above.]

[0478] V 1 When the atom is fluorine, compound (I-1) can be prepared by reacting compound (M1-2) with compound (M2-3) in the presence of a base.

[0479] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of them.

[0480] Examples of bases used in reactions include alkali metal carbonates and alkali metal hydrides.

[0481] In the reaction, relative to 1 mole of compound (M1-2), compound (M2-3) 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 2 moles.

[0482] The reaction temperature is typically in the range of 0–200°C. The reaction time is typically in the range of 0.5–24 hours.

[0483] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (I-1).

[0484] V 1 When the atom is chlorine, bromine, or iodine, compound (I-1) can be prepared by reacting compound (M1-2) with compound (M2-3) in the presence of a base and a copper or palladium catalyst.

[0485] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of them.

[0486] Examples of bases used in reactions include alkali metal carbonates; phosphates such as trisodium phosphate and tripotassium phosphate; alkali metal hydrides; organic bases; and cyclic amines such as 1,4-diazabicyclo[2,2,2]octane and diazabicycloundecene.

[0487] Examples of copper catalysts used in reactions include copper iodide (I), copper bromide (I), copper chloride (I), and copper oxide (I). When using a copper catalyst in a reaction, the ratio of copper catalyst to compound (M1-2) is typically 0.01 to 0.5 moles.

[0488] Examples of palladium catalysts used in the reaction include palladium(II) acetate and tris(dibenzylacetone)dipalladium(O). When using a palladium catalyst in the reaction, it is typically used in a ratio of 0.01 to 0.2 moles relative to 1 mole of compound (M1-2).

[0489] Ligands can be used in the reaction as needed. Examples of ligands used in the reaction include acetylacetone, Salen, phenanthroline, triphenylphosphine, and 4,5'-bis(diphenylphosphine)-9,9'-dimethylxanthene. When using ligands in the reaction, the ratio of ligand to compound (M1-2) is usually 0.01 to 0.5 moles.

[0490] In the reaction, relative to 1 mole of compound (M1-2), compound (M2-3) 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 2 moles.

[0491] The reaction temperature is typically in the range of 0–200°C. The reaction time is typically in the range of 0.5–24 hours.

[0492] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (I-1).

[0493] In compound (M2-3), R 1 For R A or R B The compounds are commercially available compounds or can be manufactured using known methods.

[0494] Manufacturing Method 6

[0495] Compound (I-a) can be prepared according to the following scheme.

[0496]

[0497] [In the formula, X] a X represents a chlorine atom, a bromine atom, or an iodine atom. b Indicates SR 2 Alternatively, a hydrogen atom; other symbols represent the same meaning as described above.

[0498] First, the process of producing a compound represented by formula (M3-1) (hereinafter referred to as compound (M3-1)) from a compound represented by formula (III-1) (hereinafter referred to as compound (III-1)) is described (hereinafter referred to as process 6-A).

[0499] Compound (M3-1) can be prepared by reacting compound (III-1) with a halogenating agent.

[0500] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of them.

[0501] Examples of halogenating agents include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide.

[0502] In the reaction, the halogenating agent is usually used in a ratio of 1 to 20 moles relative to 1 mole of compound (III-1).

[0503] The reaction temperature is typically in the range of -20℃ to 200℃. The reaction time is typically in the range of 0.1 to 72 hours.

[0504] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (M3-1).

[0505] Next, the process of manufacturing compound (I-a) from compound (M3-1) will be described.

[0506] Compound (I-a) can be prepared by reacting compound (M3-1) with a compound represented by formula (R-2) (hereinafter referred to as compound (R-2)) in the presence of a metal catalyst and a base.

[0507] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of them.

[0508] Examples of metal catalysts used in the reaction include palladium catalysts such as tetra(triphenylphosphine)palladium(0), 1,1'-bis(diphenylphosphine)ferrocene palladium(II), tris(dibenzylacetone)palladium(0), and palladium acetate(II); nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II); and copper catalysts such as copper(I) iodide and copper(I).

[0509] Examples of bases used in reactions include alkali metal hydrides, alkali metal carbonates, and organic bases.

[0510] Ligands can also be used in the reaction. Examples of ligands include triphenylphosphine, 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, and 1,10-phenanthroline. When using ligands in the reaction, the ratio of ligand to compound (M3-1) is typically 0.01 to 1 mole.

[0511] In the reaction, relative to 1 mole of compound (M3-1), compound (R-2) is usually used in a ratio of 1 to 20 moles, metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and base is usually used in a ratio of 0.1 to 5 moles.

[0512] The reaction temperature is typically in the range of -20℃ to 200℃. The reaction time is typically in the range of 0.1 to 72 hours.

[0513] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (I-a).

[0514] The compound (R-2) is known or can be manufactured by known methods.

[0515] Next, the process of producing compound (I-a) from compound (III-1) will be described.

[0516] Compound (I-a) can also be prepared by reacting compound (III-1) with a compound represented by formula (R-3) (hereinafter referred to as compound (R-3)) in the presence of a halogenating agent.

[0517] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of them.

[0518] Examples of halogenating agents include bromine, iodine, sodium bromide, potassium bromide, sodium iodide, and potassium iodide.

[0519] Oxidizing agents can be used in the reaction as needed. Examples of oxidizing agents used in the reaction include hydrogen peroxide, tert-butylhydrogen peroxide, and DMSO. When using an oxidizing agent in the reaction, it is usually used in a ratio of 1 to 20 moles relative to 1 mole of compound (III-1).

[0520] In the reaction, relative to 1 mole of compound (III-1), 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.

[0521] The reaction temperature is typically in the range of 0℃ to 200℃. The reaction time is typically in the range of 0.1 to 72 hours.

[0522] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (I-a).

[0523] The compound (R-3) is known or can be manufactured by known methods.

[0524] Manufacturing Method 7

[0525] The compound represented by formula (I-S) (hereinafter referred to as compound (I-S)) can be manufactured by reacting compound (I-1) with a vulcanizing agent.

[0526]

[0527] [In the formula, the symbols represent the same meaning as above.]

[0528] The reaction takes place in a solvent or in the absence of a solvent. Examples of solvents include ethers, haloalkanes, aromatic hydrocarbons, nitriles, nitrogen-containing aromatic compounds, and mixtures of two or more of them.

[0529] Examples of vulcanizing agents include phosphorus pentasulfide and Lawson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphacyclobutane-2,4-disulfide).

[0530] In the reaction, the vulcanizing agent is usually used in a ratio of 1 to 3 moles relative to 1 mole of compound (I-1).

[0531] The reaction temperature is typically in the range of 0℃ to 200℃. The reaction time is typically in the range of 1 to 24 hours.

[0532] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (I-S).

[0533] Manufacturing Method 8

[0534] The compound represented by formula (II-S) (hereinafter referred to as compound (II-S)) can be manufactured by reacting compound (II-O) with a vulcanizing agent.

[0535]

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

[0537] The reaction can be carried out by using compound (II-O) instead of compound (I-1) and following manufacturing method 7.

[0538] Manufacturing Method 9

[0539] The compound represented by formula (I-3-H) (hereinafter referred to as compound (I-3-H)) can be prepared by reacting the compound represented by formula (M4-1) (hereinafter referred to as compound (M4-1)) with a reducing agent.

[0540]

[0541] [In the formula, the symbols represent the same meaning as above.]

[0542] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, alcohols, and mixtures of two or more of them.

[0543] Examples of reducing agents used in the reaction include sodium borohydride, sodium cyanoborohydride, and lithium aluminum hydride.

[0544] In the reaction, the reducing agent is usually used in a ratio of 1 to 2 moles relative to 1 mole of compound (M4-1).

[0545] The reaction temperature is typically in the range of 0–100°C. The reaction time is typically in the range of 0.1–24 hours.

[0546] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain the compound (I-3-H).

[0547] Manufacturing Method 10

[0548] The compound represented by formula (I-3-C) can be prepared by reacting compound (I-3-H) with compound (R-4) (hereinafter referred to as compound (R-4)) in the presence of a base.

[0549]

[0550] [In the formula, R] C This refers to C1-C6 chain hydrocarbon groups that can be substituted by one or more substituents selected from group X, and C3-C7 cycloalkyl groups that can be substituted by one or more substituents selected from group Y, and C(O)R. 46 C(O)OR 46 Or C(O)NR 46 R 47 Other symbols have the same meaning as described above.

[0551] The reaction can be carried out by using compound (I-3-H) instead of compound (II) and in accordance with manufacturing method 4.

[0552] Compound (R-4) is a commercially available compound or can be manufactured using known methods.

[0553] Manufacturing Method 11

[0554] The nitrogen oxide of the compound represented by formula (I) can be produced by reacting the compound represented by formula (I) with an oxidizing agent. The reaction can be carried out, for example, according to the methods described in Manufacturing Method 1, U.S. Patent Application Publication No. 2018 / 0009778, or International Publication No. 2016 / 121970.

[0555] The following describes the manufacturing method for the intermediate.

[0556] Reference Manufacturing Method 1

[0557] The compound represented by formula (M1-1-D) (hereinafter referred to as compound (M1-1-D)) can be prepared by reacting the compound represented by formula (M1-3) (hereinafter referred to as compound (M1-3)) with the compound represented by formula (R-5) (hereinafter referred to as compound (R-5)) in the presence of a base.

[0558]

[0559] [In the formula, R] D This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group W, or a C3-C7 cycloalkyl group that can be substituted by one or more substituents selected from group U. Other symbols have the same meaning as above.

[0560] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[0561] Examples of bases used in reactions include alkali metal hydrides, alkali metal carbonates, and organic bases.

[0562] In the reaction, relative to 1 mole of compound (M1-3), compound (R-5) 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.

[0563] The reaction temperature is typically in the range of 0–100°C. The reaction time is typically in the range of 0.1–24 hours.

[0564] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (M1-1-D).

[0565] Reference Manufacturing Method 2

[0566] Compound (M1-1-A) can be prepared by reacting a compound represented by formula (M1-2-2) (hereinafter referred to as compound (M1-2-2)) with a compound represented by formula (R-6) (hereinafter referred to as compound (R-6)).

[0567]

[0568] [In the formula, X] d This symbol represents a fluorine or chlorine atom; other symbols have the same meaning as described above.

[0569] Reactions are typically carried out in solvents. Examples of solvents used in reactions include aprotic polar solvents, alcohols, and mixtures of two or more of them.

[0570] In the reaction, a base may be used as needed. Examples of bases used in the reaction include organic bases and alkali metal carbonates. When using a base in the reaction, the base is usually used in a ratio of 0.1 to 5 moles relative to 1 mole of compound (M1-2-2).

[0571] In the reaction, compound (R-6) is typically used in a ratio of 1 to 100 moles relative to 1 mole of compound (M1-2-2).

[0572] The reaction temperature is typically in the range of 25℃ to 200℃. The reaction time is typically in the range of 0.1 to 48 hours.

[0573] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (M1-1-A).

[0574] Compound (R-6) is a commercially available compound or can be manufactured using known methods.

[0575] Reference Manufacturing Method 3

[0576] Compound (M1-3) can be produced by reacting compound (M1-2-2) with ammonia.

[0577]

[0578] [In the formula, the symbols represent the same meaning as above.]

[0579] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, nitriles, aprotic polar solvents, alcohols, water, and mixtures of two or more of them.

[0580] In the reaction, a base may be used as needed. Examples of bases used in the reaction include organic bases and alkali metal carbonates. When using a base in the reaction, the base is usually used in a ratio of 0.1 to 5 moles relative to 1 mole of compound (M1-2-2).

[0581] Ammonia can also be used in the form of solutions such as ammonia water and ammonia methanol solution.

[0582] In the reaction, ammonia is usually used in a ratio of 1 to 100 moles relative to 1 mole of compound (M1-2-2).

[0583] The reaction temperature is typically in the range of -20℃ to 100℃. The reaction time is typically in the range of 0.1 to 48 hours.

[0584] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (M1-3).

[0585] Reference Manufacturing Method 4

[0586] The compounds represented by formula (M1-2b) and (M1-2c) can be prepared by reacting the compound represented by formula (M1-2a) (hereinafter referred to as compound (M1-2a)) with an oxidizing agent. Alternatively, the compound represented by formula (M1-2c) can also be prepared by reacting the compound represented by formula (M1-2b) with an oxidizing agent.

[0587]

[0588] [In the formula, the symbols represent the same meaning as above.]

[0589] These reactions can be carried out based on manufacturing method 1.

[0590] Reference Manufacturing Method 5

[0591] Compound (M1-2a) can be prepared according to the following scheme.

[0592]

[0593] [In the formula, the symbols represent the same meaning as above.]

[0594] These reactions can be carried out based on manufacturing method 6.

[0595] The compounds represented by formula (M1-4) (hereinafter referred to as compound (M1-4)) are well known, or can be identified according to International Publication No. 2015 / 157093, International Publication No. 2016 / 109706, Organic & Biomolecular Chemistry, 2017, 15, 4199, and the European Journal of It is manufactured according to the method described in Medicinal Chemistry, 2016, 123, 916, etc.

[0596] Reference Manufacturing Method 6

[0597] Compound (II-O) can be produced by reacting compound (M1-3) with compound (M2-1) or compound (M2-2).

[0598]

[0599] [In the formula, the symbols represent the same meaning as above.]

[0600] These reactions can be carried out by using compound (M1-3) instead of compound (M1-1-A) and following manufacturing method 2 or manufacturing method 3.

[0601] Reference Manufacturing Method 7

[0602] The compound represented by formula (M3-1-A) can be prepared by reacting the compound represented by formula (M1-6-A) (hereinafter referred to as compound (M1-6-A)) with compound (M2-1) or compound (M2-2).

[0603]

[0604] [In the formula, the symbols represent the same meaning as above.]

[0605] These reactions can be carried out by using compound (M1-6-A) instead of compound (M1-1-A) and following manufacturing method 2 or manufacturing method 3.

[0606] Reference Manufacturing Method 8

[0607] The compound represented by formula (M1-6-D) (hereinafter referred to as compound (M1-6-D)) can be manufactured according to the following scheme.

[0608]

[0609] [In the formula, the symbols represent the same meaning as above.]

[0610] First, the method for manufacturing the compound represented by formula (M1-7) (hereinafter referred to as compound (M1-7)) will be described.

[0611] Compound (M1-7) can be prepared by reacting a compound represented by formula (M1-5) (hereinafter referred to as compound (M1-5)) with ammonia. The reaction can be carried out by using compound (M1-5) instead of compound (M1-2-2) and following reference manufacturing method 3.

[0612] Next, the method for manufacturing compound (M1-6-D) will be described.

[0613] Compound (M1-6-D) can be prepared by reacting compound (M1-7) with compound (R-5) in the presence of a base. The reaction can be carried out by using compound (M1-7) instead of compound (M1-3) and following Reference Preparation Method 1.

[0614] Reference Manufacturing Method 9

[0615] The compound (M1-6-A) can be prepared according to the following scheme.

[0616]

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

[0618] First, the method for manufacturing the compound represented by formula (M1-8-A) (hereinafter referred to as compound (M1-8-A)) will be described.

[0619] Compound (M1-8-A) can be prepared by reacting compound (M1-4) with compound (R-6). The reaction can be carried out by using compound (M1-4) instead of compound (M1-2-2) and following reference preparation method 2.

[0620] Next, the method for manufacturing compound (M1-6-A) will be described.

[0621] Compound (M1-6-A) can be prepared by reacting compound (M1-8-A) with a halogenating agent. The reaction can be carried out by using compound (M1-8-A) instead of compound (III-1) and following step 6-A of manufacturing method 6.

[0622] Reference Manufacturing Method 10

[0623] The compound represented by formula (M3-1-B) (hereinafter referred to as compound (M3-1-B)) can be manufactured according to the following scheme.

[0624]

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

[0626] First, the method for manufacturing the compound represented by formula (M3-2) (hereinafter referred to as compound (M3-2)) will be described.

[0627] Compound (M3-2) can be prepared by reacting compound (M1-7) with compound (M2-1) or compound (M2-2). These reactions can be carried out by using compound (M1-7) instead of compound (M1-1-A) and following manufacturing method 2 or manufacturing method 3.

[0628] Next, the method for manufacturing compound (M3-1-B) will be described.

[0629] Compound (M3-1-B) can be prepared by reacting compound (M3-2) with compound (R-1) in the presence of a base. The reaction can be carried out by using compound (M3-2) instead of compound (II) and following preparation method 4.

[0630] Reference Manufacturing Method 11

[0631] The compound represented by formula (III-1-A) (hereinafter referred to as compound (III-1-A)) can be manufactured according to the following scheme.

[0632]

[0633] [In the formula, the symbols represent the same meaning as above.]

[0634] Compound (III-1-A) can be prepared by reacting compound (M1-8-A) with compound (M2-1) or compound (M2-2). These reactions can be carried out by using compound (M1-8-A) instead of compound (M1-1-A) and following manufacturing method 2 or manufacturing method 3.

[0635] Reference Manufacturing Method 12

[0636] The compound represented by formula (III-1-B) (hereinafter referred to as compound (III-1-B)) can be manufactured according to the following scheme.

[0637]

[0638] [In the formula, the symbols represent the same meaning as above.]

[0639] First, the method for manufacturing the compound represented by formula (III-2-B) (hereinafter referred to as compound (III-2-B)) will be described.

[0640] Compound (III-2-B) can be prepared by reacting a compound represented by formula (M1-9) (hereinafter referred to as compound (M1-9)) with compound (M2-1) or compound (M2-2). These reactions can be carried out by using compound (M1-9) instead of compound (M1-1-A) and according to manufacturing method 2 or manufacturing method 3.

[0641] Next, the method for manufacturing compound (III-1-B) will be described.

[0642] Compound (III-1-B) can be prepared by reacting compound (III-2-B) with compound (R-1) in the presence of a base. The reaction can be carried out by using compound (III-2-B) instead of compound (II) and following preparation method 4.

[0643] Reference Manufacturing Method 13

[0644] Compound (M1-9) can be produced by reacting compound (M1-4) with ammonia.

[0645]

[0646] [In the formula, the symbols represent the same meaning as above.]

[0647] The reaction can be carried out by using compound (M1-4) instead of compound (M1-2-2) and following reference manufacturing method 3.

[0648] Reference Manufacturing Method 14

[0649] The compound represented by formula (III-1-P) (hereinafter referred to as compound (III-1-P)) can be prepared by reacting the compound represented by formula (M2-3-P) (hereinafter referred to as compound (M2-3-P)) with compound (M1-4).

[0650]

[0651] [In the formula, the symbols represent the same meaning as above.]

[0652] The reaction can be carried out by replacing compound (M1-2) with compound (M1-4) and compound (M2-3) with compound (M2-3-P) according to manufacturing method 5.

[0653] Reference Manufacturing Method 15

[0654] Compound (M4-1) can be manufactured according to the following scheme.

[0655]

[0656] [In the formula, R] 60 [This indicates methyl or ethyl; other symbols have the same meaning as described above.]

[0657] First, the method for manufacturing the compound represented by formula (M5) (hereinafter referred to as compound (M5)) will be described.

[0658] Compound (M5) can be produced by reacting the compound represented by formula (M6) (hereinafter referred to as compound (M6)) with compound (M1-3).

[0659] The reaction is usually carried out in a solvent. Examples of solvents include alcohols, ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[0660] A base may be used in the reaction as needed. Examples of bases include organic bases. When using a base in a reaction, it is typically used in a ratio of 1 to 5 moles relative to 1 mole of compound (M6).

[0661] In the reaction, compound (M1-3) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (M6).

[0662] The reaction temperature is typically in the range of 0℃ to 150℃. The reaction time is typically in the range of 0.5 to 12 hours.

[0663] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (M5).

[0664] Compound (M6) can be manufactured, for example, according to the method described in Journal of Biological Chemistry, 2016, 291, 14146.

[0665] Next, the method for producing compound (M4-1) from compound (M5) will be described.

[0666] Compound (M4-1) can be produced by reacting compound (M5) with the compound represented by formula (R-7) (hereinafter referred to as compound (R-7)).

[0667] The reaction is usually carried out in a solvent or in the absence of a solvent. Examples of solvents include ethers, aromatic hydrocarbons, halogenated hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of them.

[0668] In the reaction, compound (R-7) is typically used in a ratio of 1 to 50 moles relative to 1 mole of compound (M5).

[0669] Acids or bases can be used in the reaction as needed.

[0670] Examples of acids used in the reaction include sulfonic acids such as p-toluenesulfonic acid, carboxylic acids such as acetic acid, and polyphosphoric acid. When using an acid in the reaction, the acid is usually used in a ratio of 0.01 to 5 moles relative to 1 mole of compound (M5).

[0671] Examples of bases used in reactions include organic bases. When using a base in a reaction, the base is typically used in a ratio of 1 to 5 moles relative to 1 mole of compound (M5).

[0672] The reaction temperature is typically in the range of 0℃ to 150℃. The reaction time is typically in the range of 0.5 to 24 hours.

[0673] After the reaction is complete, post-processing operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating are performed to obtain compound (M4-1).

[0674] Compound (R-7) is a commercially available compound or can be manufactured using known methods.

[0675] Alternatively, compound (M4-1) can be produced by reacting compound (M6), compound (M1-3) and compound (R-7) in a one-step reaction (one-pot process).

[0676] The reaction can be carried out by using compound (M1-3) in a ratio of 1 to 5 moles relative to compound (M6), and compound (R-7) in a ratio of 1 to 50 moles, in accordance with the method for producing compound (M4-1) from compound (M5).

[0677] Reference Manufacturing Method 16

[0678] The compound (M2-3-P) can be prepared by reacting the compound represented by formula (M7) (hereinafter referred to as compound (M7)) with the compound represented by formula (R-8) (hereinafter referred to as compound (R-8)).

[0679]

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

[0681] The reaction can be carried out, for example, according to the method described in Organic Letters, 2020, 22, 3825.

[0682] Compounds (M7) and (R-8) are commercially available compounds or can be manufactured using known methods.

[0683] The compound of the present invention or compound X of the present invention may be used in combination or mixed with one or more components selected from groups (a), (b), (c) and (d) below (hereinafter referred to as the component).

[0684] The above-mentioned combination or use refers to the use of the compound of the present invention or compound X of the present invention with the ingredient at the same time, separately or at different times.

[0685] When the compound of the present invention or compound X of the present invention is used simultaneously with the ingredient, the compound of the present invention or compound X of the present invention and the ingredient may be contained in different formulations or in one formulation.

[0686] One aspect of the present invention is a composition comprising one or more ingredients selected from group (a), group (b), group (c) and group (d), as well as the compounds of the present invention.

[0687] One aspect of the present invention is a composition comprising one or more ingredients selected from group (a), group (b), group (c) and group (d), and compound X of the present invention (hereinafter referred to as composition A).

[0688] Group (a) consists of acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABA-agonist chloride channel antagonists (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor antagonists (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate agonist chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone analogs, multisite inhibitors, aural organ TRPV channel modulators, mite growth inhibitors, and mitochondrial A... The group comprises TP biosynthetic enzyme inhibitors, oxidative phosphorylation uncoupling agents, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin-based insecticides), chitosan synthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octamine receptor agonists, mitochondrial electron transport system complex I, II, III, and IV inhibitors, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide-based insecticides), string organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients. These are described in a classification based on IRAC mechanisms of action.

[0689] Group (b) comprises nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid and protein synthesis inhibitors (e.g., aniline-pyridine fungicides), signal transduction inhibitors, lipid and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., triazole-based DMI fungicides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact fungicides, microbial fungicides, and other fungicidal active ingredients. These are described in the FRAC-based mechanism of action classification.

[0690] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0691] Group (d) is the group containing the avoided component.

[0692] The following describes examples of combinations of this ingredient and compound X of the present invention. For example, alanycarb + SX represents a combination of alanycarb and SX.

[0693] It should be noted that the abbreviation SX indicates any one of the compounds X of the present invention selected from the compound groups SX1 to SX2299 described in the examples. Furthermore, all the ingredients described below are known ingredients and can be obtained from commercially available formulations or manufactured by known methods. When the ingredient is a microorganism, it can also be obtained from a microbial culture depository. It should be noted that the numbers in parentheses indicate CAS RN (registered trademark).

[0694] The combination of the component of group (a) above with compound X of the present invention:

[0695] Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acridine + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethr (in)+SX, alpha-cypermethrin+SX, alpha-endosulfan+SX, aluminum phosphide+SX, amitraz+SX, azadirachtin+SX, azamethiphos+SX, azinphos-ethyl+SX, azinphos-methyl+SX, azocyclotin+SX, barkof Celastrus angulatus+SX, Bendiocalb + 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 acid) + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, cartap hydrochloride Hydrochloride + SX, Cartap + SX, Chinomethionat + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, Chlor Chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin A + SX, coumaphos + SX, cryolite + SX, cyanophos + SXCyanotraniliprole + SX, Cycloaniliprole + SX, N-[2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide + SX, Cycloprothrin + SX, Cycloxaprid + SX, Cyenopyrafen + SX, Cyetpyrafen + SX, Cyflumetofen + SX, Cyfluthrin + SX, Cyhalodiamide + SX, Cyhalothrin + SX, Cyhexatin + SX, Cypermethrin + SX, Cyphenothrin + S, Cyproflanilide + SX, and other similar compounds. Cyromazine + SX, Dazomet + SX, Deltamethrin + SX, Demeton-S-methyl + SX, Diafenthiuron + SX, Diazinon + SX, Dichlorvos + SX, Dichlorvos + SX, Diclomethoate + SX, Diofol + SX, Dicrotophos + SX, Diflovidazin + SX, Diflubenzuron + SX, Dimefluthrin + SX, Dimethoate + SX, Dimethylvinphos + SX, Dimpropyridaz + SX, Dinotefuran + SX, Disodium octaborate octaborate) + SX, disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX, dried leaves of European hairy fern Dryopteris filix-mas)+SX, emamectin-benzoate+SX, empenthrin+SX, endosulfan+SX, EPN (O-ethyl O-(4-nitrophenyl)phenyl thiophosphate)+SX, epsilon-metofluthrin+SX, epsilon-momfluorothrin+SX, esfenvalerate+SX, ethiofencarb+SX, ethion+SX, etiprole+SX, ethoprophos+SX, etofenprox+SX, etoxazole+SX, extract of Artemisia absinthium+SX, extract of Azadirachta Extracts of Cassia nigricans, Butterfly pea, Symphytum officinale, Chenopodium ambrosioides, Tanacetum vulgare, Urtica dioica, and Viscum album.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, fometoquin+SX, flonicamid+SX, fluacrypyrim+SX, fluazaindol izine)+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, fluralaner+SX, fluvalinate+SX, flu... Fluxametamide + SX, Formetate + SX, Fosthiazate + SX, Furamethrin + SX, Furathiocarb + SX, Gamma-cyhalothrin + SX, Glutamine synthetase-omega / kappa HXTX-Hv1a peptide (GS-omega / kappa HXTX-Hv1a peptide) + SX, Halfenprox + SX, Halofenozide + SX, Heptafluthrin + SX, Heeptenophos + SX, Hexaflumuron + SX, Hexythiazox + SX, Potassium salt of hop beta-acid acid)+SX, hydramethylnon+SX, hydroprene+SX, imicafos+SX, imidacloprid+SX, imidaclothiz+SX, imiprothrin+SX, indazapyroxamet+SX, indoxacarb+SX, isocycloseram+SX, isofenphos+SX, isoprocarb+SX, isopropyl-O-(methoxyaminothiophosphoryl)salicylate ... Isoxathion + SX, Ivermectin + SX, Kadethrin + SX, Kappa-tefluthrin + SX, Kappa-bifenthrin + SX, Kinoprene + SX, Lambda-cyhalothrin + SX, Lepimectin + SX, Lime sulfur + SX, Lotilaner + SX, Lufenuron + SX, Machine oil 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, Momfluorothrin + SX, Monocrotophos + SX, Moxidectin + SX, Naled + SX, Nicofluprole + SX, Nicotine + SX, Nicotine-sulfate + SX, Nitenpyram + SX, Novaluron + SX, Noviflumuron + SX, Insect-repellent quinoa seed oil 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, phosphazene 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 alginatealginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, piraclofos + 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, lanyl alkaloids ( ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spintoram + SX, spinosad + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride fluoride + SX, tartaremetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX, terbufos + SX, terpene constituents of the extract of chenopodium ambrosioidesnearambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetraradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon )+SX, Thiosultap-disodium+SX, Thiosultap-monosodium+SX, Tioxazafen+SX, Tolfenpyrad+SX, Tralomethrin+SX, Transfluthrin+SX, Triazamate+SX, Triazophos+SX, Trichlorfon+SX, Triflumezopyrim+SX, Triflumuron+SX, Trimethocarb+SX, Tyclopyrazoflor+SX, Vamidothion+SX, Wood extract from Suriname extract of Quassia amara)+SX, XMC (3,5-dimethylphenyl N-methylcarbamate)+SX, xylylcarb+SX, zeta-cypermethrin+SX, zinc phosphide+SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2- [Azol-3-yl]-2-methyl-N-(1-oxothiobutyryl-3-yl)benzamide (1241050-20-3)+SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2- 2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one)(1445683-71-5)+SX, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one)(2377084-09) -6)+SX、N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9)+SX、N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazole-4-yl]-2-(methanesulfonyl)propionamide (2396747-83-2)+SX、1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolin-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)pyrrolidine-1-yl]phenyl}methyl)cyclopropaneformamide+SX、7-fluoro-N-[1-(methylthio)-2-methylpropyl-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-formamide+SX、7-fluoro-N -[1-(methanesulfonyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide +SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropane-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]pyridolo[2,3-b][1,4]oxazine -10-keto (2607927-97-7)+SX, BT crop protein Cry1Ab (BT crop protein Cry1Ab)+SX, BT crop protein Cry1Ac (BT crop protein Cry1Ac)+SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa)+SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105)+SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab)+SX, BT crop protein Vip3A (BT crop protein Vip3A)+SX, BT crop protein mCry3A (BT crop protein mCry3A)+SX, BT crop protein Cry3Ab (BT crop protein Cry3Ab)+SX, BT crop protein Cry3Bb (BT crop protein Cry3Bb)+SX, BT crop protein Cry34Ab1 / Cry35Ab1 (BT crop protein Cry34Ab1 / Cry35Ab1)+SX, Tea Leaf Roller Granulovirus BV-0001 (Adoxophyes orana granulosis virus strain BV-0001)+SX, Bean Earworm Nucleopolyhedrovirus (Anticarsia gemmatalis mNPV)+SX, Alfalfa Silver-striped Earworm Nucleopolyhedrovirus (Autographa californica mNPV)+SX, Apple Leaf Roller Granulovirus V15 (Cydiapomonella GV strain V15)+SX, Apple Leaf Roller Granulovirus V22 (Cydia pomonella GVstrain V22)+SX, Apple Helicoverpa Nucleopolyhedrovirus (Cryptophlebia leucotreta GV)+SX, Pine Caterpillar Cypovirus (Dendrolimus punctatus cypovirus)+SX, Cotton Bollworm Nucleopolyhedrovirus BV-0003 (Helicoverpa Armigera NPV strain BV-0003+SX, Helicoverpa zea NPV+SX, Lymantria dispar NPV+SX, Mamestra brassicae NPV+SXNPV+SX, Mamestraconfigurata NPV+SX, Neodiprionabietis NPV+SX, Neodiprion lecontei NPV+SX, Neodiprionsertifer NPV+SX, Nosema locustae NPV+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX, Plodia interpunctella GV+SX, Spodopteraexigua mNPV+SX, Spodoptera littoralis NPV+SX mNPV)+SX, Spodoptera litura NPV+SX, Arthrobotrysdactyloides+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 AQ177+SX, Bacillus sp. strain AQ178+SX *Bacillus sphaericus* strain AQ178 + SX, *Bacillus sphaericus* strain 2362 serotype H5a5b + SX, *Bacillus sphaericus* strain ABTS1743 + SX, *Bacillus sphaericus* serotype H5a5b + SX, *Bacillus thuringiensis* strain AQ52strain AQ52+SX, Bacillus thuringiensis strain BD#32+SX, Bacillus thuringiensis strain CR-371+SX, Bacillus thuringiensis subsp. Aizawaistrain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawaistrain AM65-52+SX, Bacillus thuringiensis subsp. Aizawaistrain GC-91+SX, Bacillus thuringiensis subsp. Aizawaistrain NB200+SX strain NB200)+SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7+SX, Bacillus thuringiensis subsp. Kurstakistrain strain ABTS351+SX, Bacillus thuringiensis subsp. Kurstakistrain strain BMP123+SX, Bacillus thuringiensis subsp. Kurstakistrain strain CCT1306+SX, Bacillus thuringiensis subsp. Kurstakistrain strain EG2348 ...EG2348+SX, Bacillus thuringiensis subsp. Kurstakistrain strain EG2348+SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7+SX, Bacillus thuringiensis subsp. Kurstakistrain strain EG2348+SX, Bacillus thuringiensis subsp. Kurstakistrain strain EG2348+SX, Bacillus thuringiensis subsp. Kurstakistrain strain EG2348+ Bacillus thuringiensis subsp. Kurstakistrain EG2348+SX, Bacillus thuringiensis subsp. Kurstakistrain EG7841+SX, Bacillus thuringiensis subsp. Kurstakistrain EVB113-19The following strains were found to contain Bacillus thuringiensis subsp. Kurstakistrain EVB113-19+SX, Bacillus thuringiensis subsp. Kurstakistrain F810+SX, Bacillus thuringiensis subsp. Kurstakistrain HD-1+SX, Bacillus thuringiensis subsp. Kurstakistrain PB54+SX, and Bacillus thuringiensis subsp. Kurstakistrain SA-11. The following strains of Bacillus thuringiensis were tested: subsp. Kurstakistrain SA-11+SX, subsp. Kurstakistrain SA-12+SX, subsp. Tenebriosis strain NB176+SX, subsp. Thuringiensis strain MPPL002+SX, subsp. Morrison+SX, var. Colmeri+SX, and var. Darmstadiensis 24-91. 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-14H-14)+SX, Bacillus thuringiensis var. japonicus strain buibui+SX, Bacillus thuringiensis var. sandiego strain M-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 strain ATCC74040)+SX, Beauveria bassiana strain GHA+SX, Beauveria brongniartii+SX, Burkholderia rinojensis strain A396+SX, Chromobacterium subtsugaestrain PRAA4-1T+SX, Dactyllela ellipsospora+SX, Decylariathaumasia+SX, Hirsutella minnesotensis+SX, Hirsutella rhossiliensis+SX, Hirsutella thompsonii+SX, Lagenidium giganteum+SX, Lecanicillium KV01 The following conidia were found: * *Lecanicillium lecanii* strain KV01 + SX, * *Verticillium lecanii* conidia of strain DAOM198499 + SX, * *Verticillium lecanii* conidia of strain DAOM216596 + SX, and * *Lecanicillium* Ve6 strain.The following strains of *Metarhizium anisopliae* were found to be infected with the following strains: *Metarhizium anisopliae* strain Ve6 + SX, *Metarhizium anisopliae* strain F52 + SX, *Metarhizium anisopliae* var. *acridum* + SX, *Metarhizium anisopliae* var. *acridum* strain BIPESCO 5 / F52 + SX, *Metarhizium flvoviride* + SX, *Monacrosporium phymatopagum* + SX, *Paecilomyces fumosoroseus* strain Apopka97 + SX, *Paecilomyces lilacinus* strain 251 + SX, and *Paecilomyces tenuipes* strain T1. strain T1)+SX, Paenibacillus popilliae+SX, Pasteuria nishizawae strain Pn1+SX, Pasteuriapenetrans+SX, Pasteuria usgae+SX, Pasteuria thornei+SX, Serratia entomophila+SX, Verticillium chlamydosporium+SX, Verticillium lecanistrain NCIM1312+SX, Wolbachia pipientis+SX.

[0696] The combination of this component of group (b) above with compound X of the present invention:

[0697] 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, benthivalicarb-isopropyl +SX, benzovindiflupyr +SX, binapacryl +SX, biphenyl (biphenyl) + SX, bitertanol + SX, bixafen + SX, blasticidin-S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, glyphosate 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 + SXCymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + 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 hydrogen phosphite +SX, dipymetitrone +SX, dithianon +SX, dodecylbenzenesulfonic acid diethylenediamine copper complex salt (II) acid bisethylenediaminecopper(II)salt)+SX, dodemorph+SX, dodine+SX, edifenphos+SX, enoxastrobin+SX, epoxiconazole+SX, etaconazole+SX, ethaboxam+SX, ethirimol+SX, etridiazole+SX, extract from Melaleuca alternifolia+SX, extract from Reynoutria sachalinensis+SX, extract from the cotyledons of lupine plantlets (“BLAD”)+SX, extract of Allium sativum+SX, extract of... Equisetumarvense)+SX, nasturtium extract (extract of Tropaeolum majus)+SX, Famoxadone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenarimol + SX, Fenbuconazole + SX, Fenfuram + SX, Fenhexamid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamid + SX, Fenpropidin + SX, Fenpropimorph + SX, Fenpyrazamine + SX, Fentinacetate + SX, Fentinchloride + SX, Fentin... hydroxide) + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxystrobin + SX, fluindapyr + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, f luoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetyl-aluminium + SX, furalaxyl + SX, furamettanyl + SX, guazatine + SX, hexaconazole + SX Hymexazole + SX, Imazalil + SX, Imibenconazole + SX, Iminoctadine + SX, Iminoctadine + SX triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX, isofetamid + SX, isoflucypram + SX, isoprethiolane + SX, isopyrazam + SX, isofamin + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, oak leaves and bark Quercus + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamid + SX, Maneb + ​​SX, Mefentrifluconazole + SX, Mepanipyrim + SX, Mepronil + SX, Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Meterylpicoxamid ... tconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofuronamide + SX, orysastrobin + SX Oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX oxolinic acid + SX Imidazole (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 bicarbonate + SX, potassium dihydrogen phosphate 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, pyr The following acrolein compounds are listed: ametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb, pyridachlometyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriofenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, and quinconazole + SX.Quinofumelin + SX, quinoxyfen + SX, quintozene + SX, saponins of chenopodium Quinoa + SX, Seboctylamine + SX, Sedaxane + SX, Silthiofam + SX, Simeconazole + SX, Sodium Hyhydrogen Carbonate + 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, triclopyricar b) +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 +SXZoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethaneimide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethaneimide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethaneimide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenyl) [2-(2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformimide (2055589-28-9)+SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformimide (2055756-21-1)+SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformimide (2062599-39-5)+SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylformimide (2101814-55-3)+SX, N'-[5-bromo-6-(1-methyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylformimide [2-(2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformimide (1817828-69-5)+SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (1362477-26-6)+SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazolin (1257056-97-5)+SX, (2Z)-3-amino-2-cyano-3-phenylacrylate ethyl ester (39491-78-6)+SX, N-[(2-chlorothiazolyl-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyr Pyridine-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, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl -2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (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-imidazol-5- Nitriles (2018316-13-5)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazolium-5-nitriles (2018317-25-2)+SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propane-2-ol (2082661-43-4)+SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propane-2-ol (2082660-27-1)+SX, ({2-methyl-5-[1-(4-methoxy- 2-Methylphenyl)-1H-pyrazol-3-yl]phenylmethyl)carbamate (1605879-98-8)+SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1616239-21-4)+SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1847460-02-9)+SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1847460-05-2)+SX,(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-enamide (1445331-27-0)+SX、(2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-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-phenyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9)+SX, N-(1-phenyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5)+SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-, diazol-3-yl]phenyl}methyl)iso 3-Zyzolidinone (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-) diazol-3-yl]phenyl}methyl)iso 3-Zyzolidinone (2098918-26-2)+SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-) Diazol-3-yl]phenyl}methyl)propionamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4- Diazol-3-yl]phenyl}methyl)propionamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4- Diazol-3-yl]phenyl}methyl)cyclopropaneformamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4- Diazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4- Diazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4- [Diazol-3-yl]phenylmethyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindole-1-yl)but-2-ylN-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine ester + SX, 3-(7-bromoindol-1-yl)but-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine ester + SX, 3-(7-bromo-4-fluoroindol-1-yl)but-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine ester + SX, 3-(3,5-dichloropyridin-2 ... [Pyridine-2-yl)carbonyl]-L-alanine ester +SX, 3-(3,5-dichloropyridin-2-yl)but-2-ylN-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine ester +SX, (1S)-1-[1-(naphthyl-1-yl)cyclopropyl]ethylN-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine ester +SX, (1S)- 1-[1-(naphthyl-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine ester + SX, (1S)-1-[1-(naphthyl-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine ester + SX, Agrobacterium radioactive strain K1026 The following strains were tested: radiobactor strain K1026 + SX, Agrobacterium radiobacterium strain K84 + SX, Bacillus amyloliquefaciens (Aveo EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, and Bacillus amyloliquefaciens strain DB102.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 B246 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 QST2808+SX, Bacillus simplex strain CGF2856+SX, Bacillus subtilis strain AQ153+SX, Bacillus subtilis strain AQ743+SXstrain 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 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 strain Y1336) + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsintrain J82 + SX, Burkholderia cepacia type Wisconsintrain M54 + SX, Candidaoleophila strain O + SX, Candida hydrolyticasaitoana+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 strain CGE234M403+SX, Fusarium oxysporum strain Fo47+SX, Gliocladium catenulatum strain J1446+SX, Paenibacillus polymyxa AC-1 strain AC-1)+SX, Paenibacillus polymyxa strain BS-0105+SX, Pantoea agglomerans strain E325+SX, Phlebiopsis giganteastrain strain VRA1992+SX, Pseudomonas aureofaciens strain TX-1+SX, Pseudomonas chlororaphis strain 63-28+SX, Pseudomonas chlororaphis strain AFS009+SX, Pseudomonas chlororaphis strain MA342 strain MA342)+SX, Pseudomonas fluorescens strain 1629RS+SX, Pseudomonas fluorescens strain A506+SX, Pseudomonas fluorescens strain CL145A+SX, Pseudomonas fluorescens strain G7090strain G7090)+SX, Pseudomonas sp. CAB-02+SX, Pseudomonas syringaestrain742RS+SX, Pseudomonas syringae strain MA-4+SX, Pseudozyma flocculosa strain PF-A22UL+SX, Pseudomonas rhodesiae strain HAI-0804+SX, Pythium oligandrum strain DV74+SX, Pythium oligandrum strain M1+SX The following strains were tested: *Streptomyces griseoviridis* strain M1 + 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* strain SKT-1 + SX, and *Trichoderma* strain T25 + SX. Trichoderma asperellum strain T25+SX, Trichoderma asperellum strain T34+SX, Trichoderma asperellum strain TV1+SX, Trichoderma atroviride strain CNCM 1-1237+SX, Trichoderma atrovirides strain LC52+SX, Trichoderma atrovirides strain IMI206040 strain (Trichoderma atroviride strain IMI206040) + 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 DSM14944 + SX, Trichoderma harzianum strain ESALQ-1303 + 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+SX, Trichoderma harzianum strain T22+SX, Trichoderma harzianum strain T39+SX T39)+SX, Trichoderma harzianum strain T78+SX, Trichoderma harzianum strain TH35+SX, Trichoderma multisporum IMI206039 strain (Trichoderma polysporum strain IMI206039) + SX, Trichoderma stromaticum + SX, Trichoderma virens G-41 strain + SX, Trichoderma virens GL-21 strain + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX.

[0698] The combination of the component of group (c) above with compound X of the present invention:

[0699] 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) abscisic acid + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, 2-fluoro-N-(3-methoxyphenyl)-7H-purine-6-amine (anisiflupurin) + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate sulfate + SX, chlormequat chloride + SX, chlorpropham + SX, choline chloridechloride) + 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, Gibberellin A3 + SX A3)+SX, inabenfide+SX, kinetin+SX, lipochitooligosaccharide SP104+SX, mefluidide+SX, mepiquat-chloride+SX, oxidized glutathione+SX, pacrobutrazol+SX, pendimethalin+SX, prohexandione-calcium+SX, prohydrojasmon+SX, pyraflufen-ethyl+SX, sintofen+SX, sodium 1-naphthaleneacetate+SX, sodium cyanate cyanate)+SX, thidiazuron+SX, triapenthenol+SX, Tribufos+SX, trinexapac-ethyl+SX, uniconazole-P+SX, 2-(naphthalene-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-phenylquinazoline-2-yl)amino]-1-propanol+SX, Claroideoglomus strainThe following strains were used: *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 RTI-801* + SX, and *Rhizophagus irregularis DAOM* strain 197198. 197198)+SX, Azorhizobium caulinodans+SX, Azospirillum amazonense+SX, Azospirillum brasilense XOH+SX, Azospirillum brasilense Ab-V5+SX, Azospirillum brasilense Ab-V6+SX, Azospirillum caulinodans+SX, Azospirillum halopraeferens+SX, Azospirillum mirakense+SX, Azospirillum lipoferum+SX, Bradyrhizobium elkanii SEMIA 587+SX, Bradyrhizobium elkanii SEMIA 587 5019 strain (Bradyrhizobium elkanii SEMIA 5019) + SX, TA-11 strain (Bradyrhizobium japonicum TA-11) + SX, USDA110 strain (Bradyrhizobium japonicum USDA110) + SX, and Liaoning slow-growing rhizobium strain (Bradyrhizobium elkanii SEMIA 5019) + SX.The following strains of rhizobium were used: * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * ** * ... Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropicali + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, and Sinorhizobium yellow mosaik virus weak strain + SX.

[0700] The combination of the component of group (d) above with compound X of the present invention:

[0701] Anthraquinone + SX, DEET + SX, Icaridin + SX.

[0702] The ratio of compound X to the present ingredient is not particularly limited, but can be expressed in weight ratios (compound X:the present ingredient) of 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.

[0703] Compound X of this invention is effective against harmful arthropods such as harmful insects and mites, as well as harmful nematodes and harmful mollusks. Examples of harmful arthropods, nematodes, and mollusks include the following.

[0704] Hemiptera: Planthoppers such as *Laodelphax striatellus*, *Nilaparvatalugens*, *Sogatella furcifera*, *Peregrinus maidis*, *Javesella pellucida*, *Perkinsiella saccharicida*, and *Tagosodesorizicolus* belong to the family Delphacidae; leafhoppers such as *Nephotettix cincticeps*, *Nephotettix virescens*, *Nephotettix nigropictus*, *Recilia dorsalis*, *Empoasca onukii*, *Empoasca fabae*, *Dalbulus maidis*, and *Cofana*. Cicadidae, such as *Cicadellidae*; Aphrophoridae, such as *Philaenus spumarius*; Cercopidae, such as *Mahanarva posticata* and *Mahanarva fimbriolata*.Beet aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), apple aphid (Aphis pomi), spiraecola aphid (Aphis spiraecola), peach aphid (Myzus persicae), plum short-tailed aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), rose apple aphid (Dysaphis plantaginea), cabbage tube aphid (Lipaphis erysimi), potato long-tube aphid (Macrosiphumeuphorbiae), eggplant ditch-weaver aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), cereal tube aphid (Rhopalosiphumpadi), corn aphid (Rhopalosiphum maidis), orange aphid (Toxoptera citricida), peach pink-tailed aphid (Hyalopterus pruni), sorghum aphid (Melanaphis) The aphid family includes: *Sacchari*, *Tetraneura nigriabdominalis*, *Ceratovacuna lanigera*, *Eriosoma lanigerum*, and *Sitobionavenae*; the root aphid family includes: *Daktulosphaira vitifoliae*, *Phylloxera devastatrix*, *Phylloxera notabilis*, and *Phylloxera russellae*; and the ball aphid family includes: *Adelgestsugae*, *Adelges piceae*, and *Aphrastasia pectinatae*.The species include the black rice bug (Scotinophara lurida), the Malayan black rice bug (Scotinophara coarctata), the black-bearded green rice bug (Nezara antennata), the northern two-spotted bug (Eysarcoris aeneus), the large-spined white-spotted bug (Eysarcoris lewisi), the broad-spotted two-spotted bug (Eysarcoris ventralis), the false two-spotted bug (Eysarcoris annamita), the tea-winged bug (Halyomorpha halys), the green rice bug (Nezara viridula), the brown bug (Euschistus heros), the red-banded bug (Piezodorus guildinii), the rice bug (Oebalus pugnax), and the stink bug (Dichelops melacanthus), belonging to the family Pentatomidae; the burrowing brown bug (Scaptocoris). Cydnidae (soil bugs such as *Castanea*); Alydidae (spider bugs such as *Riptortus clavatus*, *Leptocorisa chinensis*, and *Leptocorisa acuta*); Coreidae (leaf bugs such as *Cletus punctiger* and *Leptoglossus australis*); Lygaeidae (long bugs such as *Caverelius saccharivorus*, *Togo hemipterus*, and *Blissusleucopterus*); Trigonotylus caelestialium (red-bearded mirid bug), Stenotus rubrovittatus (red-striped mirid bug), and Stenodema (two-spined narrow-spotted mirid bug). Miridae (including the mirid bug *Calcarata* and *Lyguslineolaris*); Aleyrodidae (including the whitefly family *Trialeurodes vaporariorum*, *Bemisia tabaci*, *Dialeurodes citri*, *Aleurocanthus spiniferus*, *Aleurocanthus camelliae*, and *Pealiuseuryae*).The species include: *Abgrallaspis cyanophylli*, *Aonidiella aurantii*, *Diaspidiotus perniciosus*, *Pseudaulacaspispentagona*, *Unaspis yanonensis*, and *Unaspis citri*, belonging to the family Diaspididae; *Ceroplastes rubens*, belonging to the family Coccidae; *Icerya purchasi* and *Icerya seychellarum*, belonging to the family Margarodidae; *Phenacoccus solani*, *Phenacoccus solenopsis*, and *Planococcus rubens*, belonging to the family Planococcus. The family Pseudococcidae includes species such as *Pseudococcus comstocki*, *Planococcus citri*, *Pseudococcus calceolariae*, *Pseudococcus longispinus*, and *Brevennia rehi*. The family Psyllidae includes species such as *Diaphorina citri*, *Trioza erytreae*, *Cacopsylla pyrisuga*, *Cacopsylla chinensis*, *Bactericera cockerelli*, and *Cacopsylla pyricola*. The family Psyllidae includes species such as *Corythucha ciliata* and *Corythucha ciliata*. The family Tingidae includes species such as *Marmorata*, *Stephanitis nashi*, and *Stephanitis pyrioides*; the family Cimicidae includes species such as *Cimex lectularius* and *Cimex hemipterus*; and the family Cicadidae includes species such as *Quesada gigas*.The Reduviidae family includes assassin bugs such as the harassing kissing bug (Triatoma infestans), the broad-spotted kissing bug (Triatoma rubrofasciata), the two-part kissing bug (Triatoma dimidiata), and the long red kissing bug (Rhodonius prolixus).

[0705] Lepidoptera: Rice stem borer (Chilo suppressalis), Taiwan rice stem borer (Chilo polychrysus), rice white stem borer (Scirpophaga innotata), rice stem borer (Scirpophaga incertulas), Rupela albina, rice leaf roller (Cnaphalocrocis medinalis), broad-striped leaf roller (Marasmia patnalis), rice leaf roller (Marasmia exigua), cotton leaf roller (Notarcha derogata), Asian corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), cabbage leaf borer (Hellula undalis), grape leaf cutter moth (Herpetogramma luctuosale), bluegrass moth (Pediasiateterrellus), rice three-spotted stem borer (Nymphula) Crombidae (grass moths such as *Diatraea saccharalis*, *Leucinodes orbonalis*); Pyralidae (corn borers such as *Elasmopalpus lignosellus*, *Plodia interpunctella*, *Euzophera batangensis*, *Cadra cautella*); Spodoptera litura (beet armyworm), *Spodoptera exigua* (sugar beet armyworm), *Mythimna separata* (army armyworm), *Mamestrabrassicae* (cabbage armyworm), *Sesamia inferens* (large corn borer), *Spodoptera mauritia* (gray-winged armyworm), *Naranga aenescens* (rice leafminer), and *Spodoptera* (grassland armyworm). The following are listed: frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Autographa nigrisigna, Plusiafestucae, Chrysodeixis includens, and Trichoplusia spp.Noctuidae include: *Heliothis virescens* (tobacco bud noctuid moth), *Helicoverpa armigera* (cotton bollworm), *Helicoverpa zea* (grain noctuid moth), *Anticarsia gemmatalis* (bean noctuid moth), *Alabama argillacea* (cotton leaf noctuid moth), and *Hydraecia immanis* (hopvine borer); Pieridae include: *Pieris rapae* (cabbage white butterfly); *Grapholita molesta* (pear fruit moth), *Grapholita dimorpha* (crab fruit moth), *Leguminivora glycinivorella* (soybean fruit moth), *Matsumuraesesazukivora* (soybean leafroller), and *Adoxophyes orana* (apple leafroller). This includes species such as *Fascata*, *Adoxophyeshonmai*, *Homona magnanima*, *Archips fuscocupreanus*, *Cydia pomonella*, *Tetramoera schistaceana*, *Epinotia aporema*, *Citripestis sagittiferella*, and *Lobesia botrana* (all belonging to the Tortricidae family); *Caloptilia theivora* and *Phyllonorycterringoniella* (all belonging to the Gracillariidae family); *Carposinidae* (all belonging to the Carposina sasakii family); and *Leucoptera coffeella*, *Lyonetia clerkella*, and *Lyonetia spp.* Examples of moths include the family Lyonetiidae (such as *Prunella prunifoliella*), the genera *Lymantria* (such as *Lymantriadispar*), and the genus *Euproctis* (such as *Euproctis pseudoconspersa*).Lymantriidae (e.g., diamondback moth); Plutellidae (e.g., diamondback moth); Gelechiidae (e.g., peach twig moth, sweet potato moth, red boll moth, potato moth, *Pectinophora gossypiella*, potato moth, *Tuta absoluta*); Arctiidae (e.g., fall webworm); Castniidae (e.g., sugarcane borer); Cossidae (e.g., aromatic wood-boring moth); Geometridae (e.g., giant bridge-building moth, *Ascotis selenaria*); Parasa (e.g., green tussock moth). Limacodidae (including *Limacodidae*, *Stathmopoda masinissa*, etc.); Sphingidae (including *Acherontialachesis*, etc.); Sesiidae (including *Nokona feralis*, *Synanthedonhector*, *Synanthedon tenuis*, etc.); Hesperiidae (including *Parnara guttata*, etc.); Tinedae (including *Tinea translucens*, *Tineola bisselliella*, etc.).

[0706] Thysanoptera: Thripidae (Frankliniella occidentalis), palm thistle (Thrips palmi), yellow thrips (Scirtothrips dorsalis), tobacco thrips (Thrips tabaci), flower thrips (Frankliniella intonsa), rice thrips (Stenchaetothrips biformis), American thorny thrips (Echinothrips americanus), avocado thrips (Scirtothrips perseae), etc.; Phlaeothripidae (Haplothrips aculeatus), etc.

[0707] Diptera: Anthomyiidae (including species such as *Delia platura*, *Delia antiqua*, and *Pegomya cunicularia*); Ulidiidae (including species such as *Tetanopsmyopaeformis*); Agromyzidae (including species such as *Agromyza oryzae*, *Liriomyza sativae*, *Liriomyza trifolii*, and *Chromatomyia horticola*); Chloropidae (including species such as *Chlorops oryzae*); Bactrocera cucurbitae (including species such as *Bactrocera dorsalis*, *Bactrocera latifrons*, and *Bactrocera cucurbitae*). Fruit flies include: *Bactroceratryoni*, *Ceratitis capitata*, *Rhagoletis pomonella*, and *Rhacochlaena japonica* (all belonging to the family Tephritidae); rice leaf miners (*Hydrelliagriseola*), *Hydrellia philippina*, and *Hydrellia sasakii* (all belonging to the family Ephydridae); fruit flies including *Drosophila suzukii* and *Drosophila melanogaster* (all belonging to the family Drosophilidae); flea flies including *Megaselia spiracularis* (all belonging to the family Phoridae); midges including *Clogmia albipunctata* (all belonging to the family Psychodidae); and mushroom midges including *Bradysia*. Sciaridae (e.g., *Difformis*); Cecidomyiidae (e.g., *Mayetiola destructor*, *Orseolia oryzae*); Diopsidae (e.g., *Diopsis macrophthalma*).The following species are included: Glossinidae (flies such as *Glossina palpalis* and *Glossina morsitans*); Simuliidae (flies such as *Simulium japonicum* and *Simulium damnosum*); Phlebotominae (flies such as *Tipula aino*, *Tipula oleracea*, and *Tipula paludosa*); Tipulidae (mosquitoes such as *Tipula aino*, *Tipula oleracea*, and *Tipula paludosa*); Culexpipiens pallens, Culextritaeniorhynchus, Culexpipiens f. molestus, Culex quinquefasciatus, Culexpipiens pipiens, Culex vishnui, Aedes albopictus, and Aedes aegypti. Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles salbimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus, and other mosquitoes (Culicidae); Prosimulium yezoensis, Simulium ornatum, and other fly families (Simulidae); Tabanidae, Tabanus trigonus, and other fly families (Tabanidae); housefly (Musca domestica), stable fly (Muscina). Muscidae (flies such as *Stabulans*, *Stomoxyscalcitrans*, and *Haematobia irritans*); Calliphoridae (flies); Sarcophagidae (flies);Chironomidae include species such as *Chironomus plumosus*, *Chironomus yoshimatsui*, and *Glyptotendipestokunagai*; Fannidae are also included.

[0708] Coleoptera: Diabrotica spp.For example, the western corn rootworm (Diabrotica virgifera virgifera), the southern corn rootworm (Diabrotica undecimpunctatahowardi), the northern corn rootworm (Diabrotica barberi), the Mexican corn rootworm (Diabrotica virgiferazeae), the spotted cucumber leaf beetle (Diabrotica balteata), the South American leaf beetle (Diabrotica speciosa), the bean leaf beetle (Cerotoma trifurcata), the grain leaf beetle (Oulema melanopus), the cucumber beetle (Aulacophorafemoralis), the yellow striped flea beetle (Phyllotreta striolata), the cabbage flea beetle (Phyllotretacruciferae), the western black flea beetle (Phyllotreta pusilla), the rapeseed flea beetle (Psylliodeschrysocephala), the hop flea beetle (Psylliodes punctulata), the potato beetle (Leptinotarsadecemlineata), and the rice leaf beetle (Oulema). Chrysomelidae (leaf beetles), including *Colaspis brunnea*, *Chaetocnema pulicaria*, *Chaetocnema confinis*, *Epitrix cucumeris*, *Dicladispa armigera*, *Myochrousdenticollis*, *Laccoptera quadrimaculata*, and *Epitrix hirtipennis*; Carabidae (ground beetles), including *Stenolophus lecontei* and *Clivina impressifrons*; and Anomalacuprea, Anomaala rufocuprea, Anomaala albopilosa, Popillia japonica, and Heptophylla. The genera *Picea*, *Rhizotrogus majalis*, *Tomarus gibbosus*, and *Holotrichia spp.* are mentioned.The species include: June horned beetle (Phyllophaga crinita) and other horned beetles (Phyllophaga spp.); Argentine rhinoceros beetle (Diloboderus abderus) and other larvae (Diloboderus spp.) (Scarabaeidae); coffee bean weevil (Araecerus coffeae) and other longhorned weevils (Anthriibidae); sweet potato ant weevil (Cylas formicarius) and other ant weevils (Aponidae); Brazilian bean weevil (Zabrotes subfasciatus) and other legume weevils (Bruchidae); bark beetle (Tomicus piniperda) and coffee berry bark beetle (Hypothenemus hampei) and other bark beetles (Scolytidae); West Indian sweet potato weevil (Euscepes postfasciatus), alfalfa leaf weevil (Hyperapostica), and maize weevil (Sitophilus). The genus *Aracanthus* includes: *zeamais*, *Sitophilus oryzae*, *Sitophilus granarius*, *Echinocnemus squameus*, *Lissorhoptrus oryzophilus*, *Rhabdoscelus lineatocollis*, *Anthonomus grandis*, *Sphenophorus venatus*, *Sphenophorus callosus*, *Sternechus subsignatus*, *Sphenophorus levis*, *Scepticus griseus*, *Scepticus uniformis*, and *Aracanthus mourei*.The following beetles are included: * *Eutinobothrus brasiliensis* (cowworm), * *Tribolium castaneum*, * *Tribolium confusa*, * *Alphitobius diaperinus* (mushroom beetle), * *Coccinellidae* (ladybug), * *Lyctus brunneus*, * *Rhizopertha dominica* (beetle), * *Ptinidae* (spider beetle), * *Anoplophora malasiaca*, * *Migdolus fryanus*, * *Aromia bungii* (longhorn beetle), * *Melanotus okinawensis* (click beetle), * *Agriotes* (click beetle). The family Elateridae includes click beetles such as *fuscicollis*, *Melanotus legatus*, *Anchastus* spp., *Conoderus* spp., *Ctenicera* spp., *Limonius* spp., and *Aeolus* spp.; the family Staphylinidae includes rove beetles such as *Paederus fuscipes*; the family Dermestidae includes small dermestid beetles such as *Anthrenus verbasci*, *Dermestes maculates*, and *Trogodermagranarium*; and the family Lasioderma serricorne and Stegobium. Animals include the family Anobidae (such as *Paniceum*); the family Laemophloeidae (such as *Cryptolestes ferrigineus*); the family Silvanidae (such as *Oryzaephilus surinamensis*); and the family Nitidulidae (such as *Brassicogethes aeneus*).

[0709] Orthoptera: Migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetesterminifera), Red-winged locust (Nomadacrisseptemfasciata), Brown migratory locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamusitalicus), Long-fronted grasshopper (Melanoplus differentialis), Two-banded grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clearwing locust (Camnula pellucida), Desert locust (Schistocerca gregaria), Yellow-winged insect king (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Small-winged rice locust (Oxya yezoensis), Japanese rice locust (Oxya The family Acrididae includes species such as the Japanese yellow-spined locust (Patanga succincta); the family Gryllotalpidae includes species such as the African mole cricket (Gryllotalpa orientalis); the family Gryllidae includes species such as the domestic cricket (Acheta domestica) and the yellow-faced oil cricket (Teleogryllus emma); and the family Tettigoniidae includes species such as the Mormon cricket (Anabrus simplex).

[0710] Hymenoptera: Tenthredinidae (leaf bee family), including species like *Athalia rosae* and *Athalia japonica*; genera such as *Solenopsis* (fire ant), *Solenopsis geminata* (tropical fire ant), *Atta* (brown leaf-cutting ant), *Acromyrmex* (leaf-cutting ant), *Paraponera clavata* (bullet ant), *Ochetellus glaber* (hairless stink ant), *Monomoriumpharaonis* (small yellow house ant), *Linepithema humile* (Argentine ant), *Formica japonica* (Japanese black brown ant), *Pristomyrmex punctutus* (striked-breasted leaf-cutting ant), and *Pheidole* (broad-knotted big-headed ant). Formic ants (Camponotus spp.), including *Camponotus noda*, *Pheidolemegacephala*, *Camponotus japonicus*, and *Camponotus obscuripes*; ants (Pogonomyrmex spp.), including *Pogonomyrmex occidentalis*; fire ants (Wasmania spp.), including *Wasmania auropunctata*; and yellow ants (Anoplolepis gracilipes), including those belonging to the family Formicidae; wasps (Vespa mandarinia), hairy horned wasps (Vespa simillima), false giant wasps (Vespa analis), black-breasted wasps (Vespa velutina), and domestic wasps (Polistes jokahamae), including those belonging to the family Vespidae; and large tree wasps (Urocerus). Families such as *Gigas* (Siricidae) and *Bethylidae* (Byrhynchidae).

[0711] Blattodea: Includes species such as the German cockroach (Blattella germanica) and the family Ectobiidae; species such as the American cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Australian cockroach (Periplaneta australasiae), brown-spotted cockroach (Periplaneta brunnea), and oriental cockroach (Blattaorientalis); species such as the northern subterranean termite (Reticulitermes speratus), the Formosan subterranean termite (Coptotermes formosanus), the small jacaranda termite (Incisitermes minor), the domesticated termite (Cryptotermes domesticus), the black-winged subterranean termite (Odontotermes formosanus), the Neotermite koshunensis, and the Glyptotermes. The termites include species such as *Glyptotermes satsumensis*, *Glyptotermes nakajimai*, *Glyptotermes fuscus*, *Hodotermopsis sjostedti*, *Coptotermes guangzhouensis*, *Reticulitermes amamianus*, *Reticulitermes miyatakei*, *Reticulitermes kanmonensis*, *Nasutitermestakasagoensis*, *Pericapritermes nitobei*, *Sinocapritermes mushae*, and *Cornitermes cumulans*, all belonging to the family Termitidae.

[0712] Siphonaptera: Family Pulicidae (human flea), Family Ctenocephalides felis (cat flea), Family Ctenocephalides canis (dog flea), Family Xenopsylla cheopis (mouse flea), Family Echidnophaga gallinacea (bird flea); Family Hectopsyllidae (skin-penetrating flea), Family Ceratophyllida ...

[0713] Order Psocodae: Human head louse (Pediculus humanus capitis) and other lice (Pediculus); pubic louse (Pthirus pubis) and other pubic louse (Phtirus); blood louse (Haematopinus suis) and other blood louse (Haematopinus); calves' jawed louse (Linognathus vituli), sheep's jawed louse (Linognathus ovillus), buffalo blind louse (Solenopotescapillatus) and other lice family (Linognathidae); livestock and bird louse family (Bovicoliidae) including cattle louse (Bovicola bovis), sheep's wool louse (Bovicolaovis), Bovicola breviceps, Damalina forficula, and Werneckiella spp.; dog-biting louse (Trichodectes) The following are family groups of lice: Trichodectidae (including *Canis* and *Felicola subrostratus*); Menoponidae (including *Menopon gallinae*, *Menacanthus stramineus*, and *Trinotonspp.*); Trimenoponidae (including *Cummingsia spp.*); Trogiidae (including *Trogium pulsatorium*); and Liposcelidae (or Liposcelididae) (including *Liposcelis corrodens*, *Liposcelis bostrychophila*, *Liposcelis pearmani*, and *Liposcelisentomophila*).

[0714] Thysanura: Lepismatidae such as Ctenoepisma villosa and Lepisma saccharina.

[0715] Acari (order Acari): Tetranychidae family of species such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, and Oligoychus spp.; Citrus gall mite Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus schlechtendali, and Aceria The family Eriophyidae includes species such as *Diospyri*, *Aceria tosichella*, and *Shevtchenkella* sp.; the family Tarsonemidae includes species such as *Polyphagotarsonemus latus*; the family Tenuipalpidae includes species such as *Brevipalpus phoenicis*; and the family Tuckerellidae.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, including the family Ixodidae (Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus decoloratus); Argasidae (Argas persicus, Ornithodoros hermsi, Ornithodorosturicata); Acaridae (Tyrophagus putrescentiae, Tyrophagus similis); Pyroglyphidae (Dermatophagoides farinae, Dermatophagoides pteronyssinus); and Cheyletus eruditus and Cheyletus malathus. Carnivorous mites include the family Cheyletidae, such as *Cheyletus moorei* and *Cheyletiella yasguri*.The following are species of mites: sheep itch mites (Psoroptes ovis), horse itch mites (Psoroptes equi), Knemidocoptes mutans, ear mites (Otodectes cynotis), and skin mites (Chorioptes spp.); scabies mites (Sarcoptesidae), including cat ear mites (Notoedres cati), cat anal mites (Notoedres muris), and human scabies mites (Sarcoptes scabiei); rabbit tadpole mites (Listrophorus gibbus) and other yak mites (Listrophorus gibbus); chicken scorpion mites (Dermanyssus gallinae); forest avian scorpion mites (Ornithonyssus sylviarum), broiler scorpion mites (Ornithonyssus bacoti) and other species in the family Psoroptidae; and Varroa mites (Varroa). This includes mites from the families Varoidae (such as *Jacobsoni*), Demodex canis, Demodex cati, and others from the family Demodicidae; Leptotrombiculidae (such as *Leptotrombidium akamushi*), Leptotrombiculidae (such as *Leptotrombidium pallidum*), and Leptotrombiculidae (such as *Leptotrombidium scutellare*).

[0716] Araneae: Eutichuridae (red-clawed spiders such as Cheiracanthium japonicum); Theridiidae (ball spiders such as Latrodectus hasseltii).

[0717] The order Polydesmida includes species such as Oxidus gracilis and Nedyopus tambanus, belonging to the family Paradoxosomatidae.

[0718] Isopoda: Armadillidium vulgare and Armadillidiidae.

[0719] Chilopoda: Scutigeridae (e.g., Thereuonema hilgendorfi); Scolopendridae (e.g., Scolopendra subspinipes); Ethopolidae (e.g., Bothropolys rugosus).

[0720] Gastropoda: Limacidae (including Limaxmarginatus and Limaxflavus); Philomycidae (including Meghimatium bilineatum); Ampullariidae (including Pomacea canaliculata); Lymnaeidae (including Austropeplea ollula).

[0721] Nematodes: Rice stem nematode (Aphelenchoides besseyi) and other nematodes of the family Aphelenchoididae; coffee nematode (Pratylenchus coffeae), piercing nematode (Pratylenchus brachyurus), neglected nematode (Pratylenchus neglectus), banana nematode (Radopholus similis) and other nematodes of the family Pratylenchidae; Javan root-knot nematode (Meloidogyne javanica), southern root-knot nematode (Meloidogyne incognita), bean root-knot nematode (Meloidogyne enerolobii), northern root-knot nematode (Meloidogyne hapla), soybean cyst nematode (Heteroderaglycines), potato golden nematode (Globodera) The family includes Heteroderidae (such as *Rostochiensis* and *Globoderapallida*); Hoplolaimidae (such as *Rotylenchulus reniformis*); Anguinidae (such as *Nothotylenchus acris* and *Ditylenchus dipsaci*); Tylenchulidae (such as *Tylenchulus semipenetrans*); Longidoridae (such as *Xiphinema index*); Trichodoridae; and Parasitaphelenchidae (such as *Bursaphelenchus xylophilus*).

[0722] Harmful insects, harmful mites and other harmful arthropods, harmful mollusks and harmful nematodes can also refer to harmful insects, harmful mites and other harmful arthropods, harmful mollusks and harmful nematodes whose drug sensitivity to insecticides, acaricides, molluscicides and nematicides has been reduced or who have developed drug resistance.

[0723] As a method for controlling harmful arthropods according to the present invention, it is carried out by directly applying an effective amount of the compound of the present invention, compound X of the present invention, or composition A to the harmful arthropods and / or to their habitats (plants, soil, houses, animals, etc.). Examples of methods for controlling harmful arthropods according to the present invention include foliar treatment, soil treatment, root treatment, spraying treatment, fumigation treatment, water surface treatment, and seed treatment.

[0724] The compounds of this invention, compound X of this invention, or composition A are typically mixed with inactive carriers such as solid carriers, liquid carriers, and gaseous carriers, and surfactants, and, as needed, formulation adjuvants such as binders, dispersants, and stabilizers are added to prepare aqueous suspensions, oil suspensions, oils, emulsions, microemulsions, microcapsules, wettable powders, water-dispersible powders, powders, granules, tablets, aerosols, resin formulations, etc. They are not limited to these formulations and can be formulated into manuals for development and use. Use the dosage forms described in FAO and WHO Specifications for Pesticides, FAO Lant Production and Protection Papers-271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517.

[0725] These formulations typically contain 0.0001 to 99% by weight of the compound of the present invention, compound X of the present invention, or composition A.

[0726] Examples of solid carriers include, for example, clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, micro powders and granules of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0727] Examples of liquid carriers 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-dimethyloctylamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0728] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[0729] Examples of surfactants include, for example, 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.). 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), AGRAL90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[0730] Examples of adjuvants for other formulations include binders, dispersants, colorants, and stabilizers. Specifically, examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), isopropyl phosphate, and butylated hydroxytoluene.

[0731] In this invention, the plant can be categorized as the whole plant, stem and leaves, flower, ear, fruit, trunk, branch, crown, seed, vegetative reproductive organs, and seedling.

[0732] Vegetative reproductive organs are organs in plants that, when cut from the main body and placed in soil, possess the ability to grow. Examples of vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms (or solid bulbs), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. It should be noted that stolons are sometimes called runners, and propagules are also called bulbils, which can be divided into broad buds and bulbils. Cuttings refer to the shoots (a general term for leaves and stems, shoots) of plants such as sweet potatoes or yams. Bulbs, corms, tubers, rhizomes, cuttings, rhizophores, or tuberous roots are collectively referred to as bulbils. The cultivation of tubers begins by planting tubers in the soil; the tubers used are generally called seed tubers.

[0733] As a method for controlling harmful arthropods by applying an effective amount of the compound of the present invention, compound X of the present invention, or composition A to the soil, examples include applying an effective amount of the compound of the present invention, compound X of the present invention, or composition A to the soil before or after transplanting plants; applying an effective amount of the compound of the present invention, compound X of the present invention, or composition A to the rhizosphere of crops that need protection from damage such as feeding by harmful arthropods; and controlling harmful arthropods that feed on plants by allowing an effective amount of the compound of the present invention, compound X of the present invention, or composition A to penetrate and transfer from the roots to the interior of the plant. More specifically, examples include: planting hole treatment (planting hole distribution, planting hole soil mixing), root treatment (root distribution, root soil mixing, root irrigation, late seedling stage root treatment), planting furrow treatment (planting furrow distribution, planting furrow soil mixing), ridge furrow treatment (ridge furrow distribution, ridge furrow soil mixing, growing season ridge furrow distribution), sowing furrow treatment (sowing furrow distribution, sowing furrow soil mixing), comprehensive treatment (whole soil distribution, whole soil mixing), ridge planting lateral treatment, water surface treatment (water surface application, water surface application after water storage), and other soil distribution treatments (growing season granule foliar distribution, distribution under the canopy or around the trunk, soil surface distribution, soil surface mixing, sowing hole distribution, and ridge surface distribution). Distribute (distribute among plants), other irrigation treatments (soil irrigation, seedling irrigation, liquid injection, basal irrigation, drip irrigation, chemical solution irrigation), seedling box treatment (distribute seedling box, irrigate seedling box, accumulate liquid in seedling box), seedling tray treatment (distribute seedling tray, irrigate seedling tray, accumulate liquid in seedling tray), seedbed treatment (distribute seedling tray, irrigate seedling tray, distribute seedling tray, soak seedling), bed soil mixing treatment (bed soil mixing, pre-sowing bed soil mixing, distribution before covering with soil at sowing, distribution after covering with soil at sowing, mixing with soil covering), and other treatments (mixing topsoil, turning in, mixing topsoil, mixing soil in rainwater drip area, planting location treatment, granular flower cluster distribution, mixing paste fertilizer).

[0734] As seed treatment, examples include the treatment of seeds or vegetative reproductive organs by the compounds of the present invention, compound X of the present invention, or composition A. More specifically, examples include: a blowing treatment in which a suspension of the compounds of the present invention, compound X of the present invention, or composition A is atomized and blown onto the surface of the seed or vegetative reproductive organ; a coating treatment in which the compounds of the present invention, compound X of the present invention, or composition A are applied to the seed or vegetative reproductive organ; an immersion treatment in a solution of the compounds of the present invention, compound X of the present invention, or composition A for a certain period of time; and a method of coating seeds or vegetative reproductive organs with a carrier containing the compounds of the present invention, compound X of the present invention, or composition A (film coating treatment, granule coating treatment, etc.). Seed potatoes are a particularly good example of the aforementioned vegetative reproductive organs.

[0735] When treating seeds or vegetative reproductive organs with composition A, composition A can be formulated into a single formulation for treating the seeds or vegetative reproductive organs, or composition A can be formulated into multiple different formulations for treating the seeds or vegetative reproductive organs multiple times. Examples of methods for treating seeds or vegetative reproductive organs multiple times with composition A include: treating a formulation containing only the compound of the present invention or compound X of the present invention as an active ingredient; air-drying the seeds or vegetative reproductive organs; and treating a formulation containing both the compound of the present invention or compound X of the present invention and this ingredient as active ingredients; air-drying the seeds or vegetative reproductive organs; and treating a formulation containing all components of this ingredient except for the treated component.

[0736] A seed or vegetative reproductive organ that retains the compound of the present invention, compound X of the present invention, or composition A of the present invention refers to a seed or vegetative reproductive organ in which the compound of the present invention, compound X of the present invention, or composition A of the present invention is attached to its surface. The aforementioned seed or vegetative reproductive organ that retains the compound of the present invention, compound X of the present invention, or composition A of the present invention may have materials other than the compound of the present invention, compound X of the present invention, or composition A of the present invention attached to the seed or vegetative reproductive organ before or after attachment.

[0737] Furthermore, when composition A adheres to the surface of a seed or vegetative reproductive organ in a layered manner, the layer consists of one or more layers. Additionally, when it consists of multiple layers, each layer may contain one or more active ingredients, or may consist of a layer containing one or more active ingredients and a layer without active ingredients.

[0738] Seeds or vegetative reproductive organs containing the compound of the present invention, compound X of the present invention, or composition A can be obtained, for example, by applying a preparation containing the compound of the present invention, compound X of the present invention, or composition A to the seeds or vegetative reproductive organs using the seed treatment method described above.

[0739] When the compounds of the present invention, compound X of the present invention, or composition A are used to control harmful arthropods in the agricultural field, the application rate is per 10,000 m³. 2 The amount of the compound of the present invention or compound X of the present invention is generally 1 to 10,000 g. When treating seeds or vegetative reproductive organs, the amount of the compound of the present invention or compound X of the present invention is generally applied in the range of 0.001 to 100 g relative to 1 kg of seeds or vegetative reproductive organs. When the compound of the present invention, compound X of the present invention, or composition A is formulated into emulsions, wettable powders, flowable formulations, etc., it is generally applied by diluting with water at an active ingredient concentration of 0.01 to 10,000 ppm, and granules, powders, etc., are generally applied directly.

[0740] In addition, the compound X or composition A of the present invention can also be treated by methods such as wrapping the crop with a resin preparation processed into sheets or threads, laying it near the crop, or spreading it in the soil around the roots of the plant.

[0741] When using the compounds of the present invention, compound X of the present invention, or composition A to control harmful arthropods inhabiting houses, the dosage for application on a flat surface is as follows: per 1m 2 The amount of the compound of the present invention or compound X of the present invention, measured by the area to be treated, is typically 0.01 to 1000 mg. When treating within a space, the amount is calculated per 1 m². 3 The amount of the compound of the present invention or compound X of the present invention in the treatment space is typically 0.01 to 500 mg. When the compound of the present invention, compound X of the present invention, or composition A is formulated into emulsions, wettable powders, flowable formulations, etc., it is usually applied by diluting with water at an active ingredient concentration of 0.1 to 10,000 ppm. Oils, aerosols, fumigants, poison baits, etc., are applied directly.

[0742] When using the compounds of the present invention, compound X of the present invention, or composition A for the prevention and control of external parasites in livestock such as cattle, horses, pigs, sheep, goats, and chickens, as well as small animals such as dogs, cats, rats, and mice, methods known in veterinary medicine can be employed. Specifically, for the purpose of systemic suppression, administration may be made, for example, by tablets, mixing with feed, suppositories, or injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.). For the purpose of non-systemic suppression, administration may be made, for example, by spraying or dripping with an oily or aqueous solution, washing the animal with a shampoo preparation, or fitting the animal with a collar or ear tag made from a resin preparation. The amount of the compound of the present invention or compound X of the present invention administered to the animal is generally in the range of 0.1 to 1000 mg per kg of the animal's body weight.

[0743] The compounds of this invention, compound X of this invention, or composition A can be used as a control agent for harmful arthropods in farmland such as dry fields, paddy fields, lawns, and orchards. Examples of plants that can be cited include the following.

[0744] Maize (dental, flint, soft, popcorn, glutinous, sweet, field maize), Rice (long-grain, short-grain, medium-grain, japonica, tropical japonica, indica, Javanese rice, paddy rice, land rice, floating rice, direct seeding, transplanting, glutinous rice), Wheat (bread wheat (dull, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, barley, each type of winter wheat, each type of spring wheat), Barley (two-row barley (= malting barley), six-row barley, oats, glutinous barley, each type of winter barley, each type of spring barley), Rye ( Winter rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (land-grown, pima-type), soybeans (mature seed harvest varieties, edamame varieties, immature harvest varieties, each with indeterminate, determinate, and sub-determinate growth types), peanuts, buckwheat, sugar beets (for sugar production, feed, root vegetables, leafy vegetables, fuel), rapeseed (winter rapeseed type, spring rapeseed type), rapeseed (winter rapeseed type, spring rapeseed type), sunflower (for oil extraction, food, ornamental use), sugarcane, tobacco, tea Trees, mulberries, nightshade vegetables (eggplant, tomato, bell pepper, chili pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, cantaloupe, etc.), cruciferous vegetables (radish, radish, horseradish, turnip, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, chrysanthemum, artichoke, lettuce, etc.), lilyaceous vegetables (leeks, onions, garlic, asparagus, etc.), umbelliferous vegetables (carrots, parsley, celery, parsnips, etc.), chenopodiaceae vegetables (spinach, red purslane, etc.), lamiaceae vegetables (perilla, mint, radish, etc.). Fruits include: strawberries, sweet potatoes, yams, taro, pome fruits (apples, pears, Japanese pears, Chinese pears, papayas, pears, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (oranges, tangerines, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants, lawns, and pasture grasses.

[0745] There are no specific limitations on the aforementioned plants as long as they are commonly cultivated varieties. These plants also include plants produced through natural hybridization, plants produced through gene mutation, F1 hybrids, and recombinant crops. Examples of recombinant crops include, for instance, hybrids of different species. Plants that have developed resistance to herbicides such as Isoxaflutole (HPPD inhibitors, including 4-hydroxyphenylpyruvate dioxygenase), imazethapyr, thifensulfuron-Methyl (ALS inhibitors, including ALS inhibitors, including EPSP inhibitors, including 5-enolpyruvate-3-phosphate synthase), glutamine synthase inhibitors, PPO inhibitors, bromooxynil, or dicamba; plants that can synthesize known selective toxins of Bacillus species such as Bacillus thuringiensis; and plants that can confer specific insecticidal activity by synthesizing gene fragments that are partially identical to endogenous genes from harmful insects and inducing gene silencing (RNAi; RNA interference) in target harmful insects.

[0746] Example

[0747] The present invention will now be described in more detail based on manufacturing examples, formulation examples, and test examples, but the present invention is not limited to these examples.

[0748] In this specification, Me represents methyl, Et represents ethyl, Pr represents propyl, i-Pr represents isopropyl, t-Bu represents tert-butyl, C2F5 represents perfluoroethyl, c-Pr represents cyclopropyl, Bn represents benzyl, Ph represents phenyl, Py2 represents 2-pyridyl, Py3 represents 3-pyridyl, and Py4 represents 4-pyridyl. When c-Pr, Ph, Py2, Py3, and Py4 have substituents, the substituent and its position are listed before the symbol. For example, 1-CN-c-Pr represents 1-cyanocyclopropyl, 3,4-F2-Ph represents 3,4-difluorophenyl, 2-C2F5-Ph represents 2-(perfluoroethyl)phenyl, 4-SO2CF3-Ph represents 4-(trifluoromethanesulfonyl)phenyl, 3,4-(OCF3)2-Ph represents 3,4-bis(trifluoromethoxy)phenyl, 3-SCF3-4-OCF3-Ph represents 3-[(trifluoromethyl)thio]-4-(trifluoromethoxy)phenyl, and 4-CF3-Py2 represents 4-(trifluoromethyl)-2-pyridyl.

[0749] First, examples of manufacturing the compound X of the present invention and its manufacturing intermediates are shown.

[0750] When using liquid chromatography / mass spectrometry (hereinafter referred to as LCMS) to determine the physical properties of a compound, the measured molecular ion value [M+H] is recorded. + Or [M-H] － Retention time (hereinafter referred to as RT). The conditions for liquid chromatography (hereinafter referred to as LC) are as follows.

[0751] [LC conditions]

[0752] Column: L-column2 ODS, inner diameter 4.6mm, length 30mm, particle size 3μm (Generally Incorporated Chemical Substances Evaluation and Research Organization).

[0753] UV measurement wavelength: 254nm

[0754] Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile

[0755] Flow rate: 2.0 mL / min

[0756] Gradient conditions: The solution is delivered using the concentration gradient described in [Table LC1].

[0757] [Table LC1]

[0758] Time (min) A liquor (%) B liquor (%) 0.01 90 10 2.00 0 100 4.00 0 100 4.01 90 10

[0759] Reference Manufacturing Example 1

[0760] In a mixture of 1.1 g of 6-bromo-3-(ethylthio)imidazo[1,2-a]pyridine-2-amine (hereinafter referred to as intermediate Z) prepared by the method described in International Publication No. 2018 / 052136 and 8 mL of THF, 0.83 g of 4-(trifluoromethyl)benzoyl chloride was added, followed by 1.1 mL of triethylamine, and the mixture was stirred at room temperature for 30 minutes. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 1.4 g of intermediate 1 represented by the following formula.

[0761]

[0762] Intermediate 1: 1 H-NMR(CDCl3)δ:9.39(1H,s),8.52(1H,s),8.07(2H,d),7.79(2H,d),7.57(1H,d),7.47(1H,d),2.75(2H,q),1.24(3H,t).

[0763] Reference Manufacturing Example 2

[0764] A mixture of 6.12 g of intermediate Z, 5.0 g of 3-(trifluoromethylthio)benzoic acid, 0.55 g of 4-(dimethylamino)pyridine, 50 mL of pyridine, and 6.47 g of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride was stirred at 100 °C for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 6.57 g of intermediate 2 represented by the following formula.

[0765]

[0766] Intermediate 2: 1 H-NMR(CDCl3)δ:8.56-8.53(2H,m),8.24(1H,s),8.10(1H,d),7.87(1H,d),7.60(1H,t),7.54(1H,d),7.39(1H,d),2.77(2H,q),1.25(3H,t).

[0767] Refer to manufacturing example 2-1

[0768] The following shows the compounds manufactured according to Reference Manufacturing Example 2 and their physical properties.

[0769] In the compound represented by formula (A-1), A 2 A 3 A 4 A 5 G 4 and R 3b The combination is any combination of compounds listed in [Table A-1].

[0770]

[0771] [Table A-1]

[0772] Intermediate A 2 ]]> A 3 ]]> A 4 ]]> A 5 ]]> G 4 ]]> [R 3b ]]> 3 [C-SCF3] CH CH CH CH [CAT] 4 [C-SCF3] CH CH CH CH Cl 5 [C-SCF3] CH CH CH N Br 6 CH [C-SCF3] CH CH CH Br 7 CH [C-SCF3] CH CH CH I 8 CH [C-SCF3] CH CH N H 12 C-I CH CH CH CH Br 13 CH C-Br CH CH CH Br 14 CH [C-OCF3] CH CH CH Cl 15 CH [C-OCH2CF3] CH CH CH Cl 16 CH C-CN CH CH CH Br 17 [C-CF3] CH [C-CF3] CH CH I 18 [C-CF3] CH C-CN CH CH Br 19 [C-CF3] CH C-Br CH CH I 20 C-Br CH C-Br CH CH I 21 C-Br CH N CH CH I 22 C-Cl CH C-Cl CH CH I 23 [C-OCF3] CH C-F CH CH Br 24 C-F C-CN CH CH CH Br 25 C-F C-F CH CH CH Br

[0773] Intermediate 3: 1 H-NMR(CDCl3)δ:8.56(1H,s),8.38(1H,s),8.23(1H,s),8.09(1H,t),7.89(1H,d),7.85-7.40(3H,m),2.78(2H,q),1.18(3H,t).

[0774] Intermediate 4: 1H-NMR(CDCl3)δ:8.63-8.61(2H,m),8.23(1H,s),8.08(1H,d),7.87(1H,d),7.75-7.48(3H,m),2.76(2H,q),1.19(3H,t).

[0775] Intermediate 5: 1 H-NMR(CDCl3)δ:8.62(1H,s),8.53(1H,d),8.34(1H,d),7.76-7.46(3H,m),7.31-7.29(1H,m),2.64(2H,q),1.19(3H,t).

[0776] Intermediate 6: 1 H-NMR(CDCl3)δ:8.53(1H,s),8.34(1H,s),7.99(2H,d),7.80(2H,d),7.56(1H,d),7.39(1H,d),2.75(2H,q),1.24(3H,t).

[0777] Intermediate 7: 1 H-NMR(CDCl3)δ:8.57(1H,s),8.44(1H,s),7.99(2H,d),7.79(2H,d),7.70-7.42(2H,m),2.73(2H,q),1.23(3H,t).

[0778] Intermediate 8: 1 H-NMR(CDCl3)δ:8.53(1H,s),8.36(1H,s),8.12-8.09(1H,m),7.84(2H,d),7.68(2H,d),6.92-6.90(1H,m),3.22(2H,q),1.32(3H,t).

[0779] Intermediate 12: 1 H-NMR(CDCl3)δ:8.52(1H,s),8.45(1H,s),8.29(1H,s),7.91-7.88(2H,m ),7.52(1H,d),7.37(1H,d),7.25-7.20(1H,m),2.75(2H,q),1.23(3H,t).

[0780] Intermediate 13: 1H-NMR(CDCl3)δ:8.53(1H,s),8.34(1H,s),7.84(2H,d),7.69(2H,d),7.56(1H,d),7.35(1H,d),2.75(2H,q),1.24(3H,t).

[0781] Intermediate 14: 1 H-NMR(CDCl3)δ:8.56(1H,s),8.35(1H,s),7.95(2H,d),7.65(1H,d),7.54(2H,d),7.35(1H,d),2.76(2H,q),1.23(3H,t).

[0782] Intermediate 15: 1 H-NMR(CDCl3)δ:8.63(1H,s),8.44(1H,s),7.97(2H,d),7.61(1H,d),7.51(2H,d),7.31(1H,d),4.48-4.36(2H,m),2.75(2H,q),1.19(3H,t).

[0783] Intermediate 16: 1 H-NMR(CDCl3)δ:8.63(1H,s),8.54(1H,s),8.07(2H,d),7.82(2H,d),7.55(1H,d),7.40(1H,d),2.76(2H,q),1.17(3H,t).

[0784] Intermediate 17: 1 H-NMR(CDCl3)δ:8.65(1H,s),8.41-8.37(2H,m),8.09(1H,s),7.92(1H,s),7.51(1H,d),7.45(1H,d),2.78(2H,q),1.25(3H,t).

[0785] Intermediate 18: 1 H-NMR(CDCl3)δ:8.54(1H,s),8.43-8.41(2H,m),8.11(1H,s),7.93-7.87(1H,m),7.53(1H,d),7.41(1H,d),2.77(2H,q),1.26(3H,t).

[0786] Intermediate 19: 1H-NMR(CDCl3)δ:8.70-8.46(1H,m),8.64(1H,s),8.28(1H,s),8.12(1H,s),7 .96(1H,s),7.54-7.48(1H,m),7.45-7.38(1H,m),2.77(2H,q),1.24(3H,t).

[0787] Intermediate 20: 1 H-NMR(CDCl3)δ:8.63(1H,s),8.27-8.22(1H,m),7.99(2H,d),7.87(1H,t),7.53-7.48(1H,m),7.44(1H,d),2.75(2H,q),1.24(3H,t).

[0788] Intermediate 21: 1 H-NMR(CDCl3)δ:9.05-9.04(1H,m),8.87(1H,d),8.64-8.62(1H,m),8.45-8.40(2H,m),7.51(1H,dd),7.44(1H,d),2.75(2H,q),1.24(3H,t).

[0789] Intermediate 22: 1 H-NMR(CDCl3)δ:8.64-8.61(1H,m),8.31-8.26(1H,m),7.82-7.78(2H,m) ,7.57(1H,t),7.50(1H,dd),7.44(1H,d),2.75(2H,q),1.33-1.19(3H,m).

[0790] Intermediate 23: 1 H-NMR(CDCl3)δ:8.55-8.54(1H,m),8.21(1H,s),7.63-7.56(3H,m),7.41(1H,d),7.20(1H,d),2.77(2H,q),1.26(3H,t).

[0791] Intermediate 24: 1 H-NMR(CDCl3)δ:8.54(1H,s),8.43(1H,s),7.85-7.82(3H,m),7.56(1H,d),7.42(1H,d),2.77(2H,q),1.25(3H,t).

[0792] Intermediate 25: 1H-NMR(CDCl3)δ:8.53-8.53(1H,m),8.30(1H,s),7.86-7.81(1H,m),7.72-7.70 (1H,m),7.56(1H,d),7.40(1H,d),7.35-7.28(1H,m),2.75(2H,q),1.24(3H,t).

[0793] In the compound represented by formula (A-1), A 2 A 3 A 4 A 5 G 4 and R 3b The combination is any combination of compounds recorded in [Table AA-1].

[0794] [Table AA-1]

[0795] Intermediate A 2 ]]> A 3 ]]> A 4 ]]> A 5 ]]> G 4 ]] [R 3b ]] 41 CH [C-CF3] CH CH CH [I 43 [C-CF3] CH CH N CH Br 44 CH CH [C-CF3] N CH Br 45 [C-CF3] CH CH N CH I 46 C-Br C-F CH CH CH [CAT] 47 [C-CF3] CH C-I CH CH I 48 [C-CF3] N CH CH CH I 50 CH C-Cl CH CH CH I 51 C-Cl CH CH CH CH I 52 CH [C-C2F5] CH CH CH I 53 C-I CH C-I CH CH I 54 CH [C-OCF3] CH CH CH Br 55 [C-OCF3] CH CH CH CH Br 56 CH [C-OCF2H] CH CH CH Br 57 [C-OCF2H] CH CH CH CH Br 58 CH [C-CF3] CH CH CH [CAT] 59 CH [C-SCF3] CH CH CH [CAT] 60 CH [C-CF3] CH CH CH Cl 61 CH [C-SCF3] CH CH CH Cl 62 [C-CF3] CH [C-CF3] CH C-F [CAT] 63 C-F C-F CH CH CH I 64 [C-OCF2H] CH [C-OCF2H] CH C-Cl I 65 CH [C-OCF2H] CH CH CH I 66 CH [C-SF5] CH CH Intermediate Ⅰ

[0796] Intermediate 41: 1 H-NMR(CDCl3)δ:8.63(1H,s),8.34(1H,s),8.06(2H,d),7.79(2H,d),7.47(2H,dd),2.74(2H,q),1.23(3H,t).

[0797] Intermediate 43: 1 H-NMR(CDCl3)δ:10.48(1H,s),8.88(1H,d),8.59(1H,s),8.53(1H,d),7.75(1H,d),7.60(1H,d),7.37(1H,dd),2.74(2H,q),1.24(3H,t).

[0798] Intermediate 44: 1 H-NMR(CDCl3)δ:10.48(1H,s),8.58-8.53(2H,m),8.15(1H,t),7.90(1H,d),7.59(1H,d),7.39-7.35(1H,m),2.73(2H,q),1.27(3H,t).

[0799] Intermediate 45: 1 H-NMR(CDCl3)δ:10.49(1H,s),8.88(1H,d),8.64-8.60(2H,m),7.75(1H,dd),7.50-7.49(2H,m),2.74(2H,q),1.24(3H,t).

[0800] Intermediate 46:1 H-NMR(DMSO-D6)δ:10.79(1H,s),8.92(1H,s),8.36(1H,dd),8.10-8.07(1H,m),7.86(1H,d),7.69(1H,dd),7.58(1H,t),2.81(2H,q),1.08(3H,t).

[0801] Intermediate 47: 1 H-NMR(CDCl3)δ:8.65-8.64(1H,m),8.45-8.43(2H,m),8.14(1H,s),7.51(1H,dd),7.42(1H,dd),4.34(1H,br s),2.77(2H,q),1.24(3H,t).

[0802] Intermediate 48: LCMS: 493 [M+H] + RT = 1.897 minutes

[0803] Intermediate 50: 1 H-NMR(DMSO-D6)δ:10.62(1H,s),8.76(1H,s),8.02(2H,d),7.63(3H,d),7.56(1H,dd),2.77(2H,q),1.08(3H,t).

[0804] Intermediate 51: 1 H-NMR(DMSO-D6)δ:10.66(1H,s),8.76-8.76(1H,m),8.04-8.04(1H,m),7. 97(1H,d),7.71-7.70(1H,m),7.65-7.55(3H,m),2.77(2H,q),1.08(3H,t).

[0805] Intermediate 52: 1 H-NMR(CDCl3)δ:8.63-8.62(1H,m),8.37(1H,br s),8.08(2H,d),7.77(2H,d),7.52-7.44(2H,m),2.74(2H,q),1.24(3H,t)

[0806] Intermediate 53: 1 H-NMR(CDCl3)δ:8.64-8.63(1H,m),8.26-8.25(1H,m),8.21-8.20(3H,m),7.52-7.42(2H,m),2.75(2H,q),1.24(3H,t)

[0807] Intermediate 54:1 H-NMR(DMSO-D6)δ:10.66(1H,s),8.76(1H,d),8.13(2H,d),7.64(1H,d),7.58-7.54(3H,m),2.77(2H,q),1.08(3H,t).

[0808] Intermediate 55: 1 H-NMR(DMSO-D6)δ:10.75(1H,s),8.77(1H,d),8.06(1H,d),7.94(1H,s),7.71(1H,t),7.66-7.64(2H,m),7.57(1H,dd),2.78(2H,q),1.08(3H,t).

[0809] Intermediate 56: 1 H-NMR(DMSO-D6)δ:10.56(1H,s),8.76(1H,d),8.08(2H,d),7.63(1H,d),7.56(1H,dd),7.40(1H,t),7.33(2H,d),2.77(2H,q),1.08(3H,t).

[0810] Intermediate 57: 1 H-NMR(DMSO-D6)δ:10.64(1H,s),8.77(1H,s),7.90(1H,d),7.78(1H,s),7. 65-7.53(3H,m),7.44(1H,d),7.35(1H,t),2.78(2H,q),1.10-1.06(3H,m).

[0811] Intermediate 58: 1 H-NMR(DMSO-D6)δ:10.90(1H,s),8.93(1H,s),8.20(2H,d),7.95(2H,d),7.86(1H,d),7.70(1H,dd),2.81(2H,q),1.09(3H,t).

[0812] Intermediate 59: 1 H-NMR(DMSO-D6)δ:10.91(1H,s),8.93(1H,s),8.20(2H,d),7.95(2H,d),7.86(1H,d),7.70(1H,d),2.81(2H,q),1.09(3H,t).

[0813] Intermediate 60: 1H-NMR(DMSO-D6)δ:10.79(1H,s),8.73(1H,dd),8.19(2H,d),7.94(2H,d),7.70(1H,dd),7.50(1H,dd),2.78(2H,q),1.08(3H,t).

[0814] Intermediate 61: 1 H-NMR(DMSO-D6)δ:10.75(1H,s),8.73(1H,dd),8.10(2H,d),7.90(2H,d),7.70(1H,dd),7.50(1H,dd),2.77(2H,q),1.08(3H,t).

[0815] Intermediate 62: 1 H-NMR(CDCl3)δ:8.79-8.77(1H,m),8.48-8.44(1H,br m),8.41-8.39(2H,m),8.10(1H,s),7.75(1H,d),7.51-7.49(1H,m),2.81(2H,q),1.27(3H,t).

[0816] Intermediate 63: 1 H-NMR(CDCl3)δ:8.63-8.62(1H,m),8.25-8.19(1H,br s),7.61(2H,t),7.53-7.43(2H,m),2.74(2H,q),1.23(3H,t).

[0817] Intermediate 64: 1 H-NMR(CDCl3)δ:8.64-8.63(1H,m),8.57-8.54(1H,br s),7.56-7.56(2H,m),7.51-7.40(2H,m),7.12-7.11(1H,m),6.79-6.42(2H,m),2.75(2H,q),1.24(3H,t).

[0818] Intermediate 65: 1 H-NMR(CDCl3)δ:8.63-8.62(1H,m),8.56-8.53(1H,br s),8.08-8.08(1H,m),7.87-7.84(1H,m),7.51-7.39(2H,m),7.35(1H,d),6.81-6.45(1H,m),2.74(2H,q),1.23(3H,t).

[0819] Intermediate 66: 1H-NMR(CDCl3)δ:8.63-8.63(1H,m),8.41-8.38(1H,br s),8.05(2H,d),7.91(2H,d),7.52-7.43(2H,m),2.74(2H,q),1.23(3H,t).

[0820] Reference Manufacturing Example 3

[0821] 830 mg of mCPBA (70% purity, containing 30% water) was added to a mixture of 500 mg of intermediate 1 and 5 mL of chloroform under ice-cold conditions, and the mixture was stirred at room temperature for 2 hours. A saturated aqueous solution of sodium bicarbonate and an aqueous solution of sodium thiosulfate were added sequentially to the resulting mixture, and extraction was performed with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 260 mg of intermediate 26.

[0822]

[0823] Intermediate 26: 1 H-NMR(CDCl3)δ:9.83(1H,s),8.78(1H,s),8.10(2H,d),7.82(2H,d),7.74(1H,d),7.60(1H,d),3.32(2H,q),1.36(3H,t).

[0824] Refer to manufacturing example 3-1

[0825] The following shows the compounds manufactured according to Reference Manufacturing Example 3 and their physical property values.

[0826] In the compound represented by formula (A-2), A 2 A 3 A 4 A 5 and R 3b The combination is any combination of compounds listed in [Table A-2].

[0827]

[0828] [Table A-2]

[0829] CH A 2 ]]> A 3 ]]> A 4 ]]> A 5 ]]> [R 3b ]]> 27 [C-SCF3] CH CH CH Br 28 CH [C-SCF3] CH CH Br 29 CH [C-C2F5] C-F CH Br 42 CH [C-CF3] CH Compound of the invention I

[0830] Intermediate 27: 1H-NMR(CDCl3)δ:9.78(1H,s),8.80-8.76(1H,m),8.27(1H,s),8.07(1H,d ),7.89(1H,d),7.72(1H,d),7.64-7.57(2H,m),3.33(2H,q),1.36(3H,t).

[0831] Intermediate 28: 1 H-NMR(CDCl3)δ:9.80(1H,s),8.77(1H,s),8.02(2H,d),7.81(2H,d),7.72(1H,d),7.59(1H,d),3.32(2H,q),1.36(3H,t).

[0832] Intermediate 29: 1 H-NMR(CDCl3)δ:10.09(1H,s),8.84-8.82(1H,m),8.36(1H,t),7.73(1H,d),7.61-7.58(2H,m),7.49(1H,d),3.32(2H,q),1.37(3H,t).

[0833] Intermediate 42: 1 H-NMR(CDCl3)δ:9.83(1H,s),8.86(1H,s),8.10(2H,d),7.80(2H,d),7.71(1H,dd),7.62(1H,d),3.31(2H,q),1.36(3H,t).

[0834] Refer to manufacturing example 4

[0835] A mixture of 1.52 g of triphosgene and 15 mL of THF was added dropwise to a mixture of 3.00 g of 4-(trifluoromethyl)-o-aminobenzoic acid and 22 mL of THF under ice-cold conditions. The resulting mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3.30 g of intermediate 30 represented by the following formula.

[0836]

[0837] Intermediate 30: 1 H-NMR(DMSO-D6)δ:11.98(1H,br s),8.10(1H,d),7.54(1H,d),7.37(1H,s).

[0838] Refer to manufacturing example 4-1

[0839] The following shows the compounds manufactured according to Reference Manufacturing Example 4 and their physical properties.

[0840]

[0841] Intermediate 31: 1 H-NMR(DMSO-D6)δ:9.92(1H,s),5.83(1H,d),5.80-5.77(1H,m),5.26(1H,d).

[0842] Reference Manufacturing Example 5

[0843] Under a nitrogen atmosphere at -78°C, 2.2 mL of potassium bis(trimethylsilyl)amide (1 mol / L THF solution) was added dropwise, and the mixture was stirred for 30 minutes. To the resulting mixture, 254 mg of intermediate 30 and 4 mL of THF were added, and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous solution of ammonium chloride was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Hexane was added to the residue, and the precipitated solid was filtered off. The solid was washed with hexane and dried under reduced pressure to give 491 mg of intermediate 32 (represented by the following formula).

[0844]

[0845] Intermediate 32: 1 H-NMR(CDCl3)δ:8.54(1H,dd),8.35(1H,s),7.67(1H,d),7.60(1H,dd),7.41(1H,dd),7.00(1H,s),6.98(1H,d),5.95(2H,br s),2.75(2H,q),1.27(3H,t).

[0846] Refer to manufacturing example 5-1

[0847] The following shows the compounds manufactured according to Reference Manufacturing Example 5 and their physical properties.

[0848]

[0849] Intermediate 33: 1 H-NMR(CDCl3)δ:8.53-8.53(1H,m),8.33(1H,s),7.80(1H,s),7.57(1H,d),7. 50(1H,dd),7.39(1H,dd),6.78(1H,d),6.14(2H,s),2.74(2H,q),1.26(3H,t).

[0850]

[0851] Intermediate 34: 1 H-NMR(CDCl3)δ:8.61-8.60(1H,m),8.28(1H,s),7.56(1H,d),7.50-7.44(2H,m),6.57-6.54(2H,m),5.96(2H,s),2.71(2H,q),1.23(3H,t).

[0852] Reference Manufacturing Example 6

[0853] A mixture of 491 mg of intermediate 32 and 11 mL of triethyl orthoformate was stirred at 100 °C for 1 hour. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The solid was washed with hexane to give 447 mg of intermediate 35 represented by the following formula.

[0854]

[0855] Intermediate 35: 1 H-NMR(CDCl3)δ:8.65(1H,dd),8.51(1H,d),8.20(1H,s),8.08(1H,d),7.77(1H,dd),7.61(1H,dd),7.50(1H,dd),2.77(2H,q),1.18(3H,t).

[0856] Refer to manufacturing example 6-1

[0857] The following shows the compounds manufactured according to Reference Manufacturing Example 6 and their physical property values.

[0858]

[0859] Intermediate 36: 1 H-NMR(CDCl3)δ:8.69-8.67(1H,m),8.65-8.64(1H,m),8.22(1H,s),8.03(1H,dd ),7.92-7.90(1H,m),7.61(1H,dd),7.52-7.49(1H,m),2.78(2H,q),1.19(3H,t).

[0860]

[0861] Intermediate 37: 1H-NMR(CDCl3)δ:8.76-8.74(1H,m),8.22-8.20(1H,m),8.14(1H,s),7.85( 1H,d),7.66(1H,dd),7.61(1H,dd),7.49(1H,d),2.77(2H,q),1.19(3H,t).

[0862] Refer to manufacturing example 7

[0863] The following shows the compounds manufactured according to Reference Manufacturing Example 3 and their physical property values.

[0864]

[0865] Intermediate 38: 1 H-NMR(CDCl3)δ:9.06(1H,dd),8.47(1H,d),8.26(1H,s),8.09(1H,d),7.78(1H,dd),7.73(1H,dd),7.68(1H,dd),3.56(2H,q),1.46(3H,t).

[0866]

[0867] Intermediate 39: 1 H-NMR(CDCl3)δ:9.06-9.05(1H,m),8.64-8.63(1H,m),8.28(1H,s),8.04(1H, dd),7.93-7.91(1H,m),7.73(1H,dd),7.69(1H,dd),3.59(2H,q),1.47(3H,t).

[0868]

[0869] Intermediate 40: 1 H-NMR(CDCl3)δ:9.14(1H,dd),8.20(1H,s),8.17-8.15(1H,m),7.85(1H,d) ,7.79(1H,dd),7.67-7.65(1H,m),7.60(1H,dd),3.57(2H,q),1.46(3H,t).

[0870] Manufacturing Example 1

[0871] 0.51 mL of iodomethane was added to a mixture of 1.2 g of intermediate 1, 0.88 g of cesium carbonate, and 6 mL of DMF under ice-cold conditions, and the mixture was stirred at room temperature for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (hexane:ethyl acetate = 1:1) to give 810 mg of compound 1 of the present invention.

[0872]

[0873] Compound 1 of this invention: 1 H-NMR(CDCl3)δ:8.30(1H,s),7.56(2H,d),7.50(1H,d),7.44-7.38(3H,m),3.55(3H,s),2.40(2H,q),1.10(3H,t).

[0874] Manufacturing Example 1-1

[0875] The following shows the compound manufactured according to Manufacturing Example 1 and its physical properties.

[0876] In the compound represented by formula (B-1), A 2 A 3 A 4 A 5 G 4 R 1 R 3b The combination of n and is any combination of compounds recorded in [Table B-1].

[0877]

[0878] [Table B-1]

[0879] CH A 2 ]]> A 3 ]]> A 4 ]]> A 5 ]]> G 4 ]]> [R 1 ]] [R 3b ]]> n 2 [C-SCF3] CH CH CH Me CH Br 0 3 [C-SCF3] CH CH CH Et CH Br 0 4 [C-SCF3] CH CH CH Me CH [CAT] 0 5 [C-SCF3] CH CH CH Me CH Cl 0 6 [C-SCF3] CH CH Me N CH Br 0 7 CH [C-SCF3] CH CH Me CH Br 0 8 CH [C-SCF3] CH CH Et CH Br 0 9 CH [C-SCF3] CH CH Me CH I 0 10 CH [C-SCF3] CH Me N C-I H 0 15 CH CH CH CH Me CH Br 0 16 C-Br CH CH CH Me CH Br 0 17 CH [C-OCF3] CH CH Me CH Cl 0 18 CH [C-OCH2CF3] CH CH Me CH Cl 0 19 C-CN CH CH CH Me CH Br 0 20 [C-CF3] CH [C-CF3] CH Me CH I 0 21 [C-CF3] C-CN CH CH Me CH Br 0 22 [C-CF3] C-Br CH CH Me C-Br I 0 23 CH C-Br CH CH Me C-Br I 0 24 CH CH N CH Me C-Cl I 0 25 CH C-Cl CH CH Me CH I 0 26 [C-OCF3] C-F CH CH Me C-F Br 0 27 C-CN CH CH CH Me C-F Br 0 28 C-F CH CH CH Me CH Br 0 32 [C-SCF3] CH CH CH Me CH Br 2 33 [C-SCF3] CH CH CH Me CH Br 2 38 CH [C-SCF3] CH CH Me CH Br 2 44 CH [C-C2F5] CH CH Me CH Br 2

[0880] Compound 2 of this invention: 1 H-NMR(CDCl3)δ:8.30(1H,s),7.70-7.66(2H,m),7.56-7.49(2H,m),7.41(1H,d),7.29-7.27(1H,m),3.58(3H,s),2.38(2H,q),1.11(3H,t).

[0881] Compound 3 of this invention: 1H-NMR(CDCl3)δ:8.30(1H,d),7.71-7.66(2H,m),7.55-7.50(2H,m),7.41(1H ,d),7.29-7.27(1H,m),4.10(2H,q),2.31(2H,q),1.34(3H,t),1.11(3H,t).

[0882] Compound 4 of this invention: 1 H-NMR(CDCl3)δ:8.51(1H,s),7.72-7.69(2H,m),7.61(1H,s),7.53(1H,d ),7.48(1H,d),7.31-7.30(1H,m),3.59(3H,s),2.39(2H,q),1.11(3H,t).

[0883] Compound 5 of this invention: 1 H-NMR(CDCl3)δ:8.19(1H,s),7.69-7.66(2H,m),7.56-7.51(2H,m),7.29-7.27(2H,m),3.56(3H,s),2.37(2H,q),1.10(3H,t).

[0884] Compound 6 of this invention: 1 H-NMR(CDCl3)δ:8.61(1H,s),8.52(1H,s),7.68-7.66(2H,m),7.54(1H,d),7.28-7.25(1H,m),3.59(3H,s),2.38(2H,q),1.10(3H,t).

[0885] Compound 7 of this invention: 1 H-NMR(CDCl3)δ:8.31(1H,s),7.53-7.41(6H,m),3.56(3H,s),2.32(2H,q),1.10(3H,t).

[0886] Compound 8 of this invention: 1 H-NMR(CDCl3)δ:8.31(1H,s),7.55-7.40(6H,m),4.08(2H,q),2.23(2H,q),1.32(3H,t),1.10(3H,t).

[0887] Compound 9 of this invention: 1 H-NMR(CDCl3)δ:8.39(1H,s),7.53-7.36(6H,m),3.53(3H,s),2.29(2H,q),1.07(3H,t).

[0888] Compound 10 of this invention: 1 H-NMR(CDCl3)δ:8.51-8.50(1H,m),8.07(1H,d),7.41-7.36(4H,m),6.95-6.93(1H,m),3.39(3H,s),3.17(2H,q),1.27(3H,t).

[0889] Compound 15 of this invention: 1 H-NMR(CDCl3)δ:8.31(1H,s),7.90-7.87(1H,m),7.56(1H,d),7.51(1H,d),7 .39(1H,d),7.31(1H,d),6.84(1H,t),3.52(3H,s),2.37(2H,q),1.12(3H,t).

[0890] Compound 16 of this invention: 1 H-NMR(CDCl3)δ:8.31(1H,s),7.50(1H,d),7.40(1H,d),7.32-7.28(4H,m),3.53(3H,s),2.40(2H,q),1.11(3H,t).

[0891] Compound 17 of this invention: 1 H-NMR(CDCl3)δ:8.23(1H,s),7.57(1H,d),7.51(2H,d),7.32(1H,d),7.00(2H,d),3.55(3H,s),2.34(2H,q),1.10(3H,t).

[0892] Compound 18 of this invention: 1 H-NMR(CDCl3)δ:8.22(1H,s),7.56(1H,d),7.45(2H,d),7.30(1H,d),6.70(2H,d),4.28-4.26(2H,m),3.54(3H,s),2.37(2H,q),1.10(3H,t).

[0893] Compound 19 of this invention: 1 H-NMR(CDCl3)δ:8.30(1H,s),7.53-7.46(6H,m),3.56(3H,s),2.47(2H,q),1.13(3H,t).

[0894] Compound 20 of this invention: 1H-NMR(CDCl3)δ:8.38(1H,s),7.90-7.87(2H,m),7.71(1H,s),7.52(1H,d),7.38(1H,d),3.57(3H,s),2.46(2H,q),1.11(3H,t).

[0895] Compound 21 of this invention: 1 H-NMR(CDCl3)δ:8.29(1H,s),7.91-7.87(2H,m),7.74(1H,s),7.50(1H,d),7.42(1H,d),3.56(3H,s),2.51(2H,q),1.13(3H,t).

[0896] Compound 22 of this invention: 1 H-NMR(CDCl3)δ:8.41(1H,t),7.80(1H,s),7.60(2H,d),7.52(1H,dd),7.38(1H,d),3.54(3H,s),2.46(2H,q),1.12(3H,t).

[0897] Compound 23 of this invention: 1 H-NMR(CDCl3)δ:8.45-8.43(1H,m),7.54-7.50(4H,m),7.39(1H,d),3.51(3H,s),2.46(2H,q),1.13(3H,t).

[0898] Compound 24 of this invention: 1 H-NMR(CDCl3)δ:8.50(1H,d),8.41(1H,dd),8.34(1H,d),8.06(1H,t),7.54-7.51(1H,m),7.38(1H,dd),3.55(3H,s),2.47(2H,q),1.13(3H,t).

[0899] Compound 25 of this invention: 1 H-NMR(CDCl3)δ:8.44-8.43(1H,m),7.52(1H,dd),7.39(1H,d),7.34-7.32(2H,m),7.22-7.20(1H,m),3.51(3H,s),2.46(2H,q),1.13(3H,t).

[0900] Compound 26 of this invention: 1H-NMR(CDCl3)δ:8.32(1H,s),7.50(1H,d),7.42(1H,d),7.21-7.19(1H,m),7 .05-7.05(1H,m),6.83-6.81(1H,m),3.54(3H,s),2.46(2H,q),1.12(3H,t).

[0901] Compound 27 of this invention: 1 H-NMR(CDCl3)δ:8.33(1H,s),7.51(1H,d),7.42-7.36(3H,m),7.25(1H,d),3.55(3H,s),2.52(2H,q),1.14(3H,t).

[0902] Compound 28 of this invention: 1 H-NMR(CDCl3)δ:8.31(1H,s),7.49(1H,d),7.40(1H,d),7.35-7.32(1H,m),7 .16-7.12(1H,m),6.91-6.88(1H,m),3.51(3H,s),2.43(2H,q),1.11(3H,t).

[0903] Compound 32 of this invention: 1 H-NMR(CDCl3)δ:8.82(1H,s),7.88-7.41(6H,m),3.53-3.43(5H,m),1.38-1.20(3H,m).

[0904] Compound 33 of this invention: 1 H-NMR(CDCl3)δ:8.97(1H,s),7.84-7.39(6H,m),4.08-3.86(2H,m),3.61-3.36(2H,m),1.35-1.17(6H,m).

[0905] Compound 38 of this invention: 1 H-NMR(CDCl3)δ:8.92-8.84(1H,s),7.75-7.55(6H,m),3.56-3.31(5H,m),1.42-1.26(3H,m).

[0906] Compound 44 of this invention: 1 H-NMR(CDCl3)δ:9.00(1H,s),7.84-7.40(5H,m),3.61-3.48(2H,m),3.40(3H,s),1.49-1.39(3H,m).

[0907] In the compound represented by formula (B-1), A 2 A 3 A 4 A 5 G 4 R 1 R 3b The combination of n and is any combination of compounds recorded in [Table C-1].

[0908] [Table C-1]

[0909]

[0910] Compound 64 of this invention: 1 H-NMR(CDCl3)δ:8.40(1H,s),7.56(2H,d),7.51(1H,dd),7.45-7.35(3H,m),3.55(3H,s),2.39(2H,q),1.10(3H,t).

[0911] Compound 65 of this invention: 1 H-NMR(CDCl3)δ:8.98(1H,s),7.88-7.49(6H,m),3.50-3.40(5H,m),1.35(3H,t).

[0912] Compound 67 of this invention: 1 H-NMR(CDCl3)δ:8.36(1H,s),8.28(1H,s),8.14(1H,s),7.44-7.31(3H,m),3.62(3H,s),2.57(2H,q),1.15(3H,t).

[0913] Compound 68 of this invention: 1 H-NMR(CDCl3)δ:8.43(1H,s),8.17(1H,d),7.90(1H,t),7.50(1H,d),7.32-7.29(2H,m),3.64(3H,s),2.65(2H,q),1.22(3H,t).

[0914] Compound 73 of this invention: 1 H-NMR(CDCl3)δ:8.47(1H,s),8.32-8.26(1H,m),8.14(1H,s),7.45(1H,d),7.35(1H,d),7.31(1H,d),3.62(3H,s),2.57(2H,q),1.15(3H,t).

[0915] Compound 75 of this invention: 1H-NMR(CDCl3)δ:8.55(1H,s),7.78(1H,dd),7.71(1H,d),7.49(1H,dd),7.30-7.27(1H,m),6.84(1H,t),3.54(3H,s),2.46(2H,q),1.13(3H,t).

[0916] Compound 76 of this invention: 1 H-NMR(CDCl3)δ:8.41(1H,s),7.99(1H,s),7.78(1H,s),7.62(1H,s),7.52(1H,dd),7.39(1H,dd),3.53(3H,s),2.46(2H,q),1.12(3H,t).

[0917] Compound 77 of this invention: LCMS: 507[M+H] + RT = 1.97 minutes

[0918] Compound 78 of this invention: 1 H-NMR(CDCl3)δ:8.42-8.41(1H,m),7.91-7.89(2H,m),7.80-7.78(1H,m),7 .60-7.57(1H,m),7.43-7.40(1H,m),4.95(2H,s),2.60(2H,q),1.18(3H,t).

[0919] Compound 83 of this invention: 1 H-NMR(CDCl3)δ:8.40-8.40(1H,m),7.50-7.47(1H,m),7.42-7.38(3H,m),6.64(2H,d),3.72(3H,s),3.53(3H,s),2.31(2H,q),1.07(3H,t).

[0920] Compound 84 of this invention: 1 H-NMR(CDCl3)δ:8.41-8.40(1H,m),7.53-7.49(1H,m),7.39-7.36(3H,m),7.13-7.10(2H,m),3.52(3H,s),2.38(2H,q),1.09(3H,t).

[0921] Compound 85 of this invention: 1H-NMR(CDCl3)δ:8.41-8.40(1H,m),7.54-7.49(2H,m),7.40-7.37(1H,m),7 .23-7.20(2H,m),7.06-7.02(1H,m),3.52(3H,s),2.37(2H,q),1.11(3H,t).

[0922] Compound 86 of this invention: 1 H-NMR(CDCl3)δ:8.41-8.40(1H,m),7.59-7.57(2H,m),7.53-7.51(1H,m),7.41-7.37(3H,m),3.55(3H,s),2.32(2H,q),1.08(3H,t).

[0923] Compound 87 of this invention: 1 H-NMR(CDCl3)δ:8.38-8.37(1H,m),7.71-7.70(1H,m),7.64-7.62(1H,m),7 .52-7.45(2H,m),7.39-7.29(2H,m),3.56(3H,s),2.37(2H,q),1.08(3H,t).

[0924] Compound 89 of this invention: 1 H-NMR(CDCl3)δ:8.45-8.43(1H,m),7.89-7.88(1H,m),7.73-7.73(2H,m),7 .54-7.51(1H,m),7.41-7.38(1H,m),3.50(3H,s),2.45(2H,q),1.14(3H,t).

[0925] Compound 90 of this invention: 1 H-NMR(CDCl3)δ:8.31(1H,dd),7.51-7.48(3H,m),7.40(1H,dd),6.99(2H,d),3.53(3H,s),2.33(2H,q),1.08(3H,t).

[0926] Compound 91 of this invention: 1 H-NMR(DMSO-D6)δ:8.58(1H,s),7.67(1H,d),7.60(1H,d),7.39(2H,d),7.31(1H,s),7.09(1H,s),3.41(3H,s),2.43(2H,q),0.96(3H,t).

[0927] Compound 92 of this invention: 1H-NMR(DMSO-D6)δ:8.59(1H,s),7.67(1H,d),7.58(1H,d),7.35(2H,d),7.22(1H,t),6.99(2H,d),3.38(3H,s),2.41(2H,q),0.96(3H,t).

[0928] Compound 93 of this invention: 1 H-NMR(DMSO-D6)δ:8.58(1H,s),7.66(1H,d),7.58(1H,d),7.26(1H,t),7.16( 1H,d),7.11-7.04(2H,m),7.07(1H,t),3.39(3H,s),2.42(2H,q),0.96(3H,t).

[0929] Compound 102 of this invention: 1 H-NMR(DMSO-D6)δ:8.72(1H,s),7.89(1H,d),7.72(1H,dd),7.56(2H,d),7.43(2H,dt),3.43(3H,s),2.42(2H,q),0.98(3H,t).

[0930] Compound 103 of this invention: 1 H-NMR(CDCl3)δ:8.20(1H,s),7.56-7.42(5H,m),7.31(1H,m),3.54(3H,s),2.29(2H,q),1.08(3H,t).

[0931] Compound 104 of this invention: 1 H-NMR(DMSO-D6)δ:8.56(1H,s),7.73(1H,t),7.54(3H,dt),7.42(2H,t),3.41(3H,s),2.37(2H,q),0.96(3H,t).

[0932] Compound 105 of this invention: 1 H-NMR(DMSO-D6)δ:8.56(1H,s),7.73(1H,t),7.56-7.52(3H,m),7.43-7.42(2H,m),3.41(3H,s),2.37(2H,q),0.96(3H,t).

[0933] Compound 106 of this invention: 1H-NMR(CDCl3)δ:8.31-8.27(1H,m),7.57-7.31(6H,m),4.06(2H,q),2.33(2H,q),1.32(3H,t),1.10(3H,t).

[0934] Compound 107 of this invention: 1 H-NMR(CDCl3)δ:8.31-8.28(1H,m),7.59-7.38(6H,m),3.92(2H,d),2.33(2 H,q),1.26-1.17(1H,m),1.10(3H,t),0.45-0.43(2H,m),0.24-0.23(2H,m).

[0935] Compound 108 of this invention: 1 H-NMR(CDCl3)δ:8.33-8.32(1H,m),7.60-7.44(6H,m),4.93(2H,s),2.52(2H,q),1.16(3H,t).

[0936] Compound 113 of this invention: 1 H-NMR(CDCl3)δ:8.40-8.39(1H,m),7.80-7.78(1H,m),7.62-7.59(1H,m),7.54-7. 51(2H,m),7.40-7.38(1H,m),7.25(1H,t),3.54(3H,s),2.45(2H,q),1.12(3H,t).

[0937] Compound 114 of this invention: 1 H-NMR(CDCl3)δ:8.52-8.51(1H,m),7.90-7.88(2H,m),7.73-7.70(2H,m),7.51-7.49(1H,m),3.59(3H,s),2.50(2H,q),1.13(3H,t).

[0938] Compound 115 of this invention: 1 H-NMR(CDCl3)δ:7.90(2H,s),7.70(1H,s),7.66(1H,d),7.49(1H,d),7.13(1H,dd),3.83(3H,s),3.57(3H,s),2.45(2H,q),1.11(3H,t).

[0939] Compound 116 of this invention: 1H-NMR(DMSO-D6)δ:8.59-8.58(1H,m),7.68-7.57(2H,m),7.32-7.26(4H,m),3.39(3H,s),2.48-2.43(2H,q),0.97(3H,t).

[0940] Compound 117 of this invention: 1 H-NMR(DMSO-D6)δ:8.60-8.60(1H,m),7.69-7.58(2H,m),7.37-7.35(2H,m),7.22-7.14(2H,m),3.39(3H,s),2.49-2.43(2H,q),0.96(3H,t).

[0941] Compound 118 of this invention: 1 H-NMR(CDCl3)δ:8.45-8.44(1H,m),7.55-7.52(1H,m),7.41-7.38(1H,m),7.12-7.08(2H,m),3.51(3H,s),2.49(2H,q),1.13(3H,t).

[0942] Compound 119 of this invention: 1 H-NMR(CDCl3)δ:8.18-8.16(1H,m),7.58-7.20(11H,m),5.27(2H,s),1.68-1.66(2H,m),0.81(3H,t).

[0943] Compound 120 of this invention: 1 H-NMR(CDCl3)δ:8.52-8.51(1H,m),8.49-8.47(1H,m),8.17-8.16(1H,m),7.97-7.95(1H,m),7 .59-7.51(3H,m),7.42-7.40(3H,m),7.26-7.24(1H,m),5.27(2H,s),1.76(2H,q),0.84(3H,t).

[0944] Compound 121 of this invention: 1 H-NMR(CDCl3)δ:8.42-8.41(1H,m),7.53-7.37(2H,m),7.08-7.07(2H,m),6 .78-6.76(1H,m),6.53-6.17(2H,m),3.53(3H,s),2.42(2H,q),1.11(3H,t).

[0945] Compound 122 of this invention: 1H-NMR(CDCl3)δ:8.43-8.42(1H,m),7.66-7.65(1H,m),7.54-7.51(2H,m),6 .95-6.93(1H,m),6.64-6.28(2H,m),3.52(3H,s),2.41(2H,q),1.11(3H,t).

[0946] Compound 123 of this invention: 1 H-NMR(CDCl3)δ:8.42-8.42(1H,m),7.55-7.51(5H,m),7.40-7.38(1H,m),3.54(3H,s),2.40(2H,q),1.10(3H,t).

[0947] Compound 124 of this invention: LCMS: 618[M+H] + RT = 2.40 minutes

[0948] Manufacturing Examples 1-2

[0949] The following shows the compounds manufactured according to Reference Manufacturing Example 3 and their physical property values.

[0950] In the compound represented by formula (B-2), A 2 A 3 A 4 A 5 G 4 R 1 R 3b The combination of n is any of the combinations listed in [Table B-2] and [Table B-3] of the compound.

[0951]

[0952] [Table B-2]

[0953] CH A 2 ]]> A 3 ]]> A 4 ]]> A 5 ]] G 4 ]] [R 1 ]] [R 3b ]] n 29 CH Me [C-CF3] C-I CH CH I 1 30 CH CH Me CH CH CH I 1 31 CH [C-CF3] Me CH CH CH Br 2 35 [C-SCF3] CH Me CH C-CN CH [CAT] 2 36 [C-SCF3] CH CH Me CH CH Cl 2 39 CH [C-SCF3] Me CH CH CH I 2 40 Me [C-SCF3] CH CH N CH H 2 45 Me C-Cl CH C-Cl CH CH Br 2 47 Me [C-OCF3] CH CH CH CH Cl 2 48 Me [C-OCH2CF3] CH CH CH Me Cl 2 49 CH CH CH Me CH CH Br 2 50 [C-CF3] CH [C-CF3] Me CH CH I 2 53 Br CH Br Me CH CH I 2 54 Br CH N Me C-CN CH I 2 55 CH CH CH Me CH CH I 2 66 [C-OCF3] CH CH ​ ​ ​ Br 2 69 [C-CF3] ​ ​ N ​ ​ Br 2 70 [C-CF3] ​ [C-CF3] ​ ​ ​ I 1 71 [C-CF3] ​ N ​ ​ ​ I 1 72 [C-CF3] ​ N ​ ​ ​ I 2 74 [C-CF3] ​ ​ N ​ ​ I 2 79 ​ ​ ​ ​ ​ ​ I 2 80 [C-CF3] ​ [C-CF3] ​ ​ [CH2CN] I 2 81 ​ [C-SCF3] CH CH CH Me Br 1 82 CH [C-CF3] CH CH CH Me Br 1 88 [C-C2F5] CH CH CH CH Me I 2 94 CH [C-OCF3] CH CH CH Me Br 1 95 [C-OCF3] CH CH CH CH Me Br 1 97 C-I CH C-I CH CH Me I 1 98 CH [C-OCF2H] CH CH CH Me Br 1 99 [C-OCF2H] CH CH CH CH Me Br 1 100 CH [C-OCF2H] CH CH CH Me Br 2 101 [C-OCF2H] CH CH CH CH Me Br 2 109 CH [C-CF3] CH CH CH Et Br 2 110 CH [C-CF3] CH CH CH CH2cPr Br 2 111 CH [C-CF3] CH CH CH [CH2CN] Br 2 112 CH CH [C-CF3] N CH Me Br 2

[0954] [Table B-3]

[0955]

[0956] Compound 29 of this invention: 1 H-NMR(CDCl3)δ:8.99(1H,s),7.84(1H,s),7.77(1H,s),7.67-7.60(2H,m),7.4 7(1H,d),3.53(3H,s),3.48-3.33(1H,m),2.90-2.40(1H,m),1.41-1.30(3H,m).

[0957] Compound 30 of this invention:1 H-NMR(CDCl3)δ:9.00(1H,s),7.62(1H,dq),7.46(1H,dd),7.40-7.30(3H,m),3.59-3.33(4H,m),2.95-2.43(1H,m),1.43-1.32(3H,m).

[0958] Compound 31 of this invention: 1 H-NMR(CDCl3)δ:8.90(1H,s),7.84-7.51(6H,m),3.71-3.22(5H,m),1.42-1.29(3H,m).

[0959] Compound 35 of this invention: 1 H-NMR(CDCl3)δ:9.10(1H,s),7.98(1H,d),7.90-7.67(5H,m),3.56-3.34(5H,m),1.40-1.36(3H,m).

[0960] Compound 36 of this invention: 1 H-NMR(CDCl3)δ:8.77(1H,s),7.82(1H,d),7.73-7.42(5H,m),3.60-3.19(5H,m),1.30-1.26(3H,m).

[0961] Compound 39 of this invention: 1 H-NMR(CDCl3)δ:8.95(1H,s),7.71-7.65(5H,m),7.50(1H,d),3.61-3.27(5H,m),1.43-1.17(3H,m).

[0962] Compound 45 of this invention: 1 H-NMR(CDCl3)δ:8.89(1H,s),7.99-7.50(6H,m),3.58-3.26(5H,m),1.44-1.30(3H,m).

[0963] Compound 47 of this invention: 1 H-NMR(CDCl3)δ:8.81(1H,s),7.69-7.68(4H,m),7.51(1H,d),7.26-7.25(1H,m),3.57-3.34(5H,m),1.38-1.33(3H,m).

[0964] Compound 48 of this invention: 1H-NMR(CDCl3)δ:8.81(1H,s),7.64-7.53(5H,m),6.98-6.93(1H,m),4.39-4.37(2H,m),3.47-3.40(5H,m),1.31-1.30(3H,m).

[0965] Compound 49 of this invention: 1 H-NMR(CDCl3)δ:8.89(1H,s),7.78-7.67(6H,m),3.46-3.31(5H,m),1.38-1.35(3H,m).

[0966] Compound 50 of this invention: 1 H-NMR(CDCl3)δ:8.92(1H,s),8.13-7.76(3H,m),7.71(1H,d),7.50(1H,d),3.58-2.91(5H,m),1.46-1.28(3H,m).

[0967] Compound 53 of this invention: 1 H-NMR(CDCl3)δ:9.04-8.92(1H,m),7.80-7.59(4H,m),7.51(1H,dd),3.59-3.16(5H,m),1.29-1.23(3H,m).

[0968] Compound 54 of this invention: 1 H-NMR(CDCl3)δ:9.07-8.43(3H,m),8.14-8.11(1H,m),7.72(1H,dd),7.51(1H,dd),3.79-2.63(5H,m),1.45-1.24(3H,m).

[0969] Compound 55 of this invention: 1 H-NMR(CDCl3)δ:9.05-8.87(1H,m),7.70(1H,dd),7.55-7.36(4H,m),3.66-2.79(5H,m),1.45-1.32(3H,m).

[0970] Compound 66 of this invention: 1 H-NMR(CDCl3)δ:8.87(1H,s),8.05-7.37(6H,m),3.51-3.43(5H,m),1.29(3H,t).

[0971] Compound 69 of this invention: 1H-NMR(CDCl3)δ:9.17(1H,s),8.45-8.21(2H,m),7.72-7.43(3H,m),3.69(3H,s),3.58-3.39(2H,m),1.52-1.40(3H,m).

[0972] Compound 70 of this invention: 1 H-NMR(CDCl3)δ:8.96(1H,s),7.97-7.92(2H,m),7.87(1H,s),7.63(1H,d),7.46(1H,d),3.60-3.29(5H,m),1.30(3H,t).

[0973] Compound 71 of this invention: 1 H-NMR(CDCl3)δ:8.72(1H,s),8.63(1H,s),8.53(1H,s),7.92(1H,s),7.41(1H,dd),7.23(1H,dd),3.15(2H,br s),2.47(3H,br s),1.05(3H,d).

[0974] Compound 72 of this invention: 1 H-NMR(CDCl3)δ:9.10-8.63(3H,br m),8.21(1H,s),7.72(1H,dd),7.51(1H,dd),3.58-2.76(5H,br m),1.57-1.54(3H,br m).

[0975] Compound 74 of this invention: 1 H-NMR(CDCl3)δ:9.17(1H,s),8.40-7.92(2H,m),7.64-7.31(3H,m),3.64-3.28(5H,m),1.42-1.30(3H,m).

[0976] Compound 79 of this invention: LCMS: 495 [M+H] + RT = 1.68 minutes

[0977] Compound 80 of this invention: LCMS: 631 [M+H] + RT = 2.07 minutes

[0978] Compound 81 of this invention: 1 H-NMR(DMSO-D6)δ:8.85(1H,s),7.80(1H,d),7.73(1H,dd),7.68(2H,d),7.50(2H,d),3.52-3.41(5H,m),1.10(3H,t).

[0979] Compound 82 of this invention: 1 H-NMR(DMSO-D6)δ:8.84(1H,s),7.80(1H,dd),7.74-7.71(3H,m),7.58(2H,d),3.52-3.40(5H,m),1.10(3H,t).

[0980] Compound 88 of this invention: LCMS: 588[M+H] + RT = 2.03 minutes

[0981] Compound 94 of this invention: LCMS: 490 [M+H] + RT = 1.78 minutes

[0982] Compound 95 of this invention: LCMS: 490 [M+H] + RT = 1.79 minutes

[0983] Compound 97 of this invention: 1 H-NMR(CDCl3)δ:9.02-9.00(1H,m),8.08-8.06(1H,m),7.82-7.77(2H,m),7.64-7.61(1H,m),7.48-7.45(1H,m),3.51(3H,s),3.49-3.37(2H,br m),1.41(3H,t).

[0984] Compound 98 of this invention: LCMS: 472[M+H] + RT = 1.62 minutes

[0985] Compound 99 of this invention: LCMS: 472[M+H] + RT = 1.62 minutes

[0986] Compound 100 of this invention: LCMS: 488 [M+H] + RT = 1.78 minutes

[0987] Compound 101 of this invention: LCMS: 488 [M+H] + RT = 1.78 minutes

[0988] Compound 109 of this invention: LCMS: 504 [M+H] + RT = 1.98 minutes

[0989] Compound 110 of this invention: LCMS: 532[M+H] + RT = 2.07 minutes

[0990] Compound 111 of this invention: LCMS: 517[M+H] + RT = 1.91 minutes

[0991] Compound 112 of this invention: 1 H-NMR(CDCl3)δ:9.13(1H,s),8.40(1H,d),8.07(1H,t),7.71-7.58(2H,m),7.53-7.45(1H,m),3.72(3H,s),3.42-3.23(2H,m),1.49(3H,t).

[0992] Compound 125 of this invention: LCMS: 548 [M+H] + RT = 2.13 minutes

[0993] Compound 126 of this invention: LCMS: 620 [M+H] + RT = 2.16 minutes

[0994] Compound 127 of this invention: LCMS: 646 [M+H] + RT = 2.24 minutes

[0995] Compound 128 of this invention: LCMS: 650 [M+H] + RT = 2.23 minutes

[0996] Compound 129 of this invention: 1 H-NMR(DMSO-D6)δ:8.94(1H,br s),8.07(1H,d),7.97(1H,d),7.73-7.63(4H,m),3.40(3H,s),3.36-3.33(2H,br m),1.19-1.12(3H,br m).

[0997] Compound 130 of this invention: 1 H-NMR(DMSO-D6)δ:8.70(1H,br s),7.91(1H,d),7.79-7.76(1H,m),7.71-7.63(4H,m),3.42-3.31(2H,br m),3.38(3H,s),1.19-1.08(3H,br m).

[0998] Compound 131 of this invention: 1 H-NMR(DMSO-D6)δ:8.83(1H,br s),7.81-7.71(2H,m),7.42-7.36(4H,m),3.50-3.41(5H,m),1.10(3H,t).

[0999] Compound 132 of this invention: 1 H-NMR(DMSO-D6)δ:8.83(1H,br s),7.81-7.70(4H,m),7.14(2H,d),3.51-3.40(5H,m),1.10(3H,t).

[1000] Compound 133 of this invention: 1 H-NMR(DMSO-D6)δ:8.91(1H,br s),7.88-7.78(4H,m),7.36(1H,d),7.16(1H,t),3.57-3.47(5H,m),1.19(3H,t).

[1001] Compound 134 of this invention: 1 H-NMR(DMSO-D6)δ:8.94(1H,s),8.07(1H,d),7.97(1H,dd),7.69-7.54(4H,br m),3.39(3H,s),3.38-3.38(2H,m),1.19-1.08(3H,br m).

[1002] Compound 135 of this invention: LCMS: 566 [M+H] + RT = 2.15 minutes

[1003] Compound 136 of this invention: LCMS: 583 [M+H] + RT = 1.66 minutes

[1004] Compound 137 of this invention: LCMS: 602 [M+H] + RT = 1.90 minutes

[1005] Compound 138 of this invention: LCMS: 554 [M+H] + RT = 1.81 minutes

[1006] Compound 139 of this invention: LCMS: 596 [M+H] + RT = 1.95 minutes

[1007] Compound 140 of this invention: LCMS: 456 [M+H] + RT = 1.85 minutes

[1008] Compound 141 of this invention: LCMS: 548 [M+H] + RT = 1.87 minutes

[1009] Compound 142 of this invention: 1H-NMR(DMSO-D6)δ:8.85(1H,br s),7.82-7.72(2H,m),7.50-7.47(2H,m),7.33(1H,t),7.24(1H,d),3.52-3.41(5H,m),1.12(3H,t).

[1010] Compound 143 of this invention: LCMS: 456 [M+H] + RT = 1.79 minutes

[1011] Manufacturing Example 2

[1012] A mixture of 370 mg of intermediate 2, 580 mg of cesium carbonate, 200 μL of 2-iodopropane, and 10 mL of DMF was stirred at 50 °C for 8 hours. Water was added to the resulting mixture, and extraction was performed with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 5 mL of chloroform was added to the residue, followed by the addition of 400 mg of mCPBA (70% purity, containing 30% water) under ice-cold conditions, and the mixture was stirred at room temperature for 2 hours. Saturated aqueous solutions of sodium bicarbonate and sodium thiosulfate were added sequentially to the resulting mixture, and extraction was performed with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 110 mg of compound 34 of the present invention.

[1013]

[1014] Compound 34 of this invention: LCMS: 550 [M+H] + RT = 2.16 minutes

[1015] Manufacturing Example 3

[1016] 45 mg of sodium borohydride and 0.5 mL of methanol were added sequentially to a mixture of 300 mg of intermediate 38 and 6 mL of THF under ice-cold conditions, and the mixture was stirred at room temperature for 2 hours. Water was added to the resulting mixture under ice-cold conditions, and the precipitated solid was filtered off. The resulting solid was washed with water and dried under reduced pressure to give 240 mg of compound 59 of the present invention, represented by the following formula.

[1017]

[1018] Compound 59 of this invention: 1 H-NMR(CDCl3)δ:9.02-9.01(1H,m),8.13(1H,d),7.59-7.56(2H,m),7.18(1H,d),7.08(1H,s),5.19(2H,d),4.77(1H,br s),3.64(2H,q),1.45(3H,t).

[1019] Manufacturing Example 3-1

[1020] The following shows the compound manufactured according to manufacturing example 3 and its physical properties.

[1021]

[1022] Compound 60 of this invention: 1 H-NMR(CDCl3)δ:9.01-9.01(1H,m),8.28(1H,s),7.57-7.54(3H,m),6.83(1H,d),5.21(2H,d),5.01(1H,br s),3.67(2H,q),1.47(3H,t).

[1023]

[1024] Compound 61 of this invention: 1 H-NMR(CDCl3)δ:9.09-9.09(1H,m),7.87(1H,d),7.67(1H,dd),7.45(1H,dd),7.23-7.20(1H,m),6.81(1H,d),5.14(2H,d),4.80(1H,br s),3.65(2H,q),1.47-1.43(3H,m).

[1025] Manufacturing Example 4

[1026] At room temperature, 0.2 mL of iodomethane and 83 mg of potassium carbonate were added sequentially to a mixture of 150 mg of compound 60 of the present invention and 3 mL of DMF, and the mixture was stirred at 80 °C for 16 hours. The resulting mixture was cooled to room temperature, and water was added. The precipitated solid was filtered, washed with water, and dried under reduced pressure to obtain 102 mg of compound 62 of the present invention represented by the following formula.

[1027]

[1028] Compound 62 of this invention: 1 H-NMR(CDCl3)δ:9.01(1H,s),8.30(1H,d),7.67(1H,d),7.59-7.56(2H,m),6.84(1H,d),5.07(2H,s),3.69(2H,q),3.07(3H,s),1.48(3H,t).

[1029] Manufacturing Example 4-1

[1030] The following shows the compound manufactured according to manufacturing example 4 and its physical properties.

[1031]

[1032] Compound 63 of this invention: 1 H-NMR(CDCl3)δ:9.01(1H,s),8.31(1H,d),7.64(1H,d),7.58-7.57(2H,m),6 .89(1H,d),5.14(2H,s),3.68(2H,q),3.57(2H,q),1.47(3H,t),1.28(3H,t).

[1033] Manufacturing Example 5

[1034] A mixture of 0.49 g of compound 7 of the present invention, 260 mg of cyclopropylboronic acid, 150 mg of [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II), 640 mg of tripotassium phosphate, 4 mL of toluene, and 0.4 mL of water was stirred at 110 °C for 2 hours. The resulting mixture was cooled to room temperature, and water was added. Extraction was performed with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (ethyl acetate:hexane = 1:1) to give 400 mg of compound 11 of the present invention, represented by the following formula.

[1035]

[1036] Compound 11 of this invention: 1 H-NMR(CDCl3)δ:7.95(1H,s),7.51-7.50(3H,m),7.42(2H,d),7.07(1H,d),3.54(3H,s ),2.26(2H,q),1.94-1.91(1H,m),1.27(3H,t),1.02-1.00(2H,m),0.73-0.70(2H,m).

[1037] Manufacturing Example 5-1

[1038] The following shows the compound manufactured according to manufacturing example 5 and its physical properties.

[1039]

[1040] Compound 12 of this invention: 1 H-NMR(CDCl3)δ:8.28(1H,s),7.68(1H,d),7.57-7.50(5H,m),7.44(2H,d),7.20-7.16(2H,m),3.58(3H,s),2.31(2H,d),1.09(3H,t).

[1041]

[1042] Compound 13 of this invention: 1 H-NMR(CDCl3)δ:8.84(1H,s),8.68(1H,d),8.36(1H,s),7.89-7.86(1H,m),7.73(1 H,d),7.59-7.53(3H,m),7.46-7.42(3H,m),3.58(3H,s),2.32(2H,q),1.10(3H,t).

[1043] Next, examples of the compound X of the present invention manufactured according to any of the manufacturing examples described in the embodiments and the manufacturing methods described in this specification are shown below.

[1044] In the compound represented by formula (L-1) (hereinafter referred to as compound (L-1)), n is 0 and R is 0. 1 Methyl, R 3b For hydrogen atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX1).

[1045]

[1046]

[1047]

[1048]

[1049] [Table L10]

[1050] 5-Fluoropyridazin-3-yl 5-Chloropyridazin-3-yl 5-Bromopyridazin-3-yl 5-Cyanopyridazin-3-yl 5-[(Trifluoromethyl)thio]pyridazin-3-yl 5-(Trifluoromethoxy)pyridazin-3-yl 5-(Trifluoromethyl)pyridazin-3-yl 5-(Perfluoroethyl)pyridazin-3-yl 5-Nitropyridazin-3-yl 6-Fluoropyridazin-3-yl 6-Chloropyridazin-3-yl 6-Bromopyridazin-3-yl 6-Cyanopyridazin-3-yl 6-[(Trifluoromethyl)thio]pyridazin-3-yl 6-(Trifluoromethoxy)pyridazin-3-yl 6-(Trifluoromethyl)pyridazin-3-yl 6-(Perfluoroethyl)pyridazin-3-yl 6-Nitropyridazin-3-yl 4-Fluoropyrimidin-2-yl 4-Chloropyrimidin-2-yl 4-Bromopyrimidin-2-yl 4-Cyanopyrimidin-2-yl 4-[(Trifluoromethyl)thio]pyrimidin-2-yl 4-(Trifluoromethoxy)pyrimidin-2-yl 4-(Trifluoromethyl)pyrimidin-2-yl 4-(Perfluoroethyl)pyrimidin-2-yl 4-Nitropyrimidin-2-yl 5-Fluoropyrimidin-2-yl 5-Chloropyrimidin-2-yl

[1051] [Table L11]

[1052] 5-Bromopyrimidin-2-yl 5-Cyanopyrimidin-2-yl 5-[(Trifluoromethyl)thio]pyrimidin-2-yl 5-(Trifluoromethoxy)pyrimidin-2-yl 5-(Trifluoromethyl)pyrimidin-2-yl 5-(Perfluoroethyl)pyrimidin-2-yl 5-Nitropyrimidin-2-yl 4-Fluoropyrazin-2-yl 4-Chloropyrazin-2-yl 4-Bromopyrazin-2-yl 4-Cyanopyrazin-2-yl 4-[(Trifluoromethyl)thio]pyrazin-2-yl 4-(Trifluoromethoxy)pyrazin-2-yl 4-(Trifluoromethyl)pyrazin-2-yl 4-(Perfluoroethyl)pyrazin-2-yl 4-Nitropyrazin-2-yl 5-Fluoropyrazin-2-yl 5-Chloropyrazin-2-yl 5-Bromopyrazin-2-yl 5-Cyanopyrazin-2-yl 5-[(Trifluoromethyl)thio]pyrazin-2-yl 5-(Trifluoromethoxy)pyrazin-2-yl 5-(Trifluoromethyl)pyrazin-2-yl 5-(Perfluoroethyl)pyrazin-2-yl 5-Nitropyrazin-2-yl

[1053] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For chlorine atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX2).

[1054] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For bromine atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX3).

[1055] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For iodine atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX4).

[1056] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For CF3, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX5).

[1057] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For hydrogen atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX6).

[1058] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For chlorine atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX7).

[1059] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For bromine atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX8).

[1060] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For iodine atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX9).

[1061] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For CF3, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX10).

[1062] In compound (L-1), n ​​is 0 and R is 0. 1Methyl, R 3b For hydrogen atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX11).

[1063] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For chlorine atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX12).

[1064] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For bromine atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX13).

[1065] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For iodine atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX14).

[1066] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For CF3, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX15).

[1067] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For hydrogen atoms, R 3c The compound is an iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX16).

[1068] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For chlorine atoms, R 3c Compounds in which iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX17).

[1069] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For bromine atoms, R 3cThe compound is an iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX18).

[1070] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For iodine atoms, R 3c Compounds in which iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX19).

[1071] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For CF3, R 3c Compounds in which iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX20).

[1072] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For hydrogen atoms, R 3c Compounds for which CF3 and T are any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX21).

[1073] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For chlorine atoms, R 3c The compound is CF3 and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX22).

[1074] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For bromine atoms, R 3c The compound is CF3 and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX23).

[1075] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For iodine atoms, R 3c The compound is CF3 and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX24).

[1076] In compound (L-1), n ​​is 0 and R is 0. 1 Methyl, R 3b For CF3, R 3cThe compound is CF3 and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX25).

[1077] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For hydrogen atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX26).

[1078] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For chlorine atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX27).

[1079] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For bromine atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX28).

[1080] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For iodine atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX29).

[1081] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For CF3, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX30).

[1082] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For hydrogen atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX31).

[1083] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For chlorine atoms, R 3cCompounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX32).

[1084] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For bromine atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX33).

[1085] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For iodine atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX34).

[1086] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For CF3, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX35).

[1087] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For hydrogen atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX36).

[1088] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For chlorine atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX37).

[1089] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For bromine atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX38).

[1090] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For iodine atoms, R 3cCompounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX39).

[1091] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For CF3, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX40).

[1092] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For hydrogen atoms, R 3c Compounds in which iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX41).

[1093] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For chlorine atoms, R 3c The compound is an iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX42).

[1094] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For bromine atoms, R 3c The compound is an iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX43).

[1095] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For iodine atoms, R 3c The compound is an iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX44).

[1096] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For CF3, R 3c The compound is an iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX45).

[1097] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For hydrogen atoms, R 3cThe compound is CF3 and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX46).

[1098] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For chlorine atoms, R 3c The compound is CF3 and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX47).

[1099] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For bromine atoms, R 3c Compounds for which CF3 and T are any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX48).

[1100] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For iodine atoms, R 3c Compounds for which CF3 and T are any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX49).

[1101] In compound (L-1), n ​​is 0 and R is 0. 1 Ethyl, R 3b For CF3, R 3c Compounds for which CF3 and T are any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX50).

[1102] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For hydrogen atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX51).

[1103] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For chlorine atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX52).

[1104] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For bromine atoms, R 3cCompounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX53).

[1105] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For iodine atoms, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX54).

[1106] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For CF3, R 3c Compounds in which T is a hydrogen atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX55).

[1107] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For hydrogen atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX56).

[1108] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For chlorine atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX57).

[1109] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For bromine atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX58).

[1110] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For iodine atoms, R 3c Compounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX59).

[1111] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For CF3, R 3cCompounds in which chlorine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX60).

[1112] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For hydrogen atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX61).

[1113] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For chlorine atoms, R 3c The compound having a bromine atom and T being any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX62).

[1114] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For bromine atoms, R 3c Compounds in which bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX63).

[1115] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For iodine atoms, R 3c The compound is a bromine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX64).

[1116] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For CF3, R 3c The compound having a bromine atom and T being any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX65).

[1117] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For hydrogen atoms, R 3c The compound is an iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred to as compound group SX66).

[1118] In compound (L-1), n ​​is 0 and R is 0. 1 Isopropyl, R 3b For chlorine atoms, R 3cCompounds in which iodine atom and T is any of the substituents listed in [Table L1] to [Table L11] (hereinafter referred...

Claims

1. The compound represented by formula (I), In formula (I), Z represents the oxygen atom. R 1 This indicates a methyl, ethyl, propyl, or isopropyl group that can be substituted by one or more substituents selected from group W. R 2 It represents ethyl, n represents 0, 1, or 2. G 1 Indicates CR 3a , G 2 Indicates CR 3b , G 3 Indicates CR 3c , G 4 Represents nitrogen atom or CR 3d , R 3a R 3b R 3c and R 3d "Same" or "different" indicates C1-C6 chain hydrocarbon groups that can be substituted with one or more halogen atoms, cyclopropyl groups, phenyl groups that can be substituted with one or more fluorine atoms, and OR groups. 12 Hydrogen atoms or halogen atoms R 12 This indicates a methyl group that can be substituted by one or more fluorine atoms. A 1 Indicates CR 4a , A 2 Indicates CR 4b , A 3 Represents nitrogen atom or CR 4c , A 4 Represents nitrogen atom or CR 4d , A 5 Represents nitrogen atom or CR 4e , R 4a and R 4e "Same" or "different" indicates methyl groups that can be substituted with one or more fluorine atoms, ethyl groups that can be substituted with one or more fluorine atoms, and OR groups. 44 cyano group, halogen atom, or hydrogen atom A 5 For CR 4e At that time, R 4e and R 1 They can form together -NR 45 -CR 41 R 42 -#,in, # indicates that R 1 The bonding positions of the nitrogen atoms. R 4b R 4c and R 4d "Same" or "different" indicates methyl groups that can be substituted with one or more fluorine atoms, ethyl groups that can be substituted with one or more fluorine atoms, and OR groups. 44 S(O) q R 41 , cyano, halogen atom, or hydrogen atom, of which R is not present. 4a R 4b R 4c R 4d and R 4e All represent hydrogen atoms, and q represents 0. R 41 and R 42 "Same" or "different" indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 44 This indicates a methyl or ethyl group that can be substituted by one or more fluorine atoms. R 45 Indicates methyl, ethyl, or hydrogen atom. Group W: The group consisting of cyclopropyl, ethoxy, phenyl, pyridyl, and cyano groups.

2. The compound according to claim 1, wherein, A 1 A 2 A 3 A 4 and A 5 The combinations are as follows: A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e The combination; A 1 For CR 4a A 2 For CR 4b A 3 For nitrogen atoms, A 4 For CR 4d A 5 For CR 4e The combination; A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For nitrogen atoms, A 5 For CR 4e A combination; or A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 It is a combination of nitrogen atoms.

3. The compound according to claim 1, wherein, A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e .

4. The compound according to claim 1, wherein, G 1 For CR 3a G 2 For CR 3b G 3 For CR 3c G 4 For CR 3d , A 1 For CR 4a A 2 For CR 4b A 3 For CR 4c A 4 For CR 4d A 5 For CR 4e .

5. A composition for controlling harmful arthropods, comprising any one of claims 1 to 4.

6. A composition comprising one or more ingredients selected from group (a), group (b), group (c) and group (d), and the compound according to any one of claims 1 to 4. Group (a): Insecticidal active ingredient, Group (b): Bactericidal active ingredient, Group (c): Plant growth regulators Group (d): Avoidable components.

7. A method for controlling harmful arthropods as a non-disease treatment, comprising applying an effective amount of the compound of any one of claims 1 to 4 or an effective amount of the composition of claim 6 to the harmful arthropod or its habitat.

8. A method for treating a seed or vegetative reproductive organ to maintain an effective amount of the compound of any one of claims 1 to 4 or an effective amount of the composition of claim 6.

9. The compound represented by formula (II), In formula (II), Z represents the oxygen atom. R 2 It represents ethyl, n represents 0 or 2, G 1 Indicates CR 3a , G 2 Indicates CR 3b , G 3 Indicates CR 3c , G 4 Represents nitrogen atom or CR 3d , R 3a R 3b R 3c and R 3d "Same" or "different" indicates C1-C6 chain hydrocarbon groups that can be substituted with one or more halogen atoms, cyclopropyl groups, phenyl groups that can be substituted with one or more fluorine atoms, and OR groups. 12 Hydrogen atoms or halogen atoms R 12 This indicates a methyl group that can be substituted by one or more fluorine atoms. A 1 Indicates CR 4a , A 2 Indicates CR 4b , A 3 Represents nitrogen atom or CR 4c , A 4 Represents nitrogen atom or CR 4d , A 5 Represents nitrogen atom or CR 4e , R 4a and R 4e "Same" or "different" indicates methyl groups that can be substituted with one or more fluorine atoms, ethyl groups that can be substituted with one or more fluorine atoms, and OR groups. 44 cyano group, halogen atom, or hydrogen atom R 4b R 4c and R 4d "Same" or "different" indicates methyl groups that can be substituted with one or more fluorine atoms, ethyl groups that can be substituted with one or more fluorine atoms, and OR groups. 44 S(O) q R 41 , cyano group, halogen atom, or hydrogen atom, among which, R does not exist 4a R 4b R 4c R 4d and R 4e All represent hydrogen atoms, and q represents 0. R 41 This refers to a C1-C6 chain hydrocarbon group that can be replaced by one or more halogen atoms. R 44 This indicates a methyl or ethyl group that can be substituted by one or more fluorine atoms.

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