Heterocyclic compound and harmful arthropod-controlling composition containing same
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Filing Date
- 2023-09-29
- Publication Date
- 2026-06-29
AI Technical Summary
Current compounds for controlling harmful arthropods do not offer excellent control efficacy against arthropod pests.
A heterocyclic compound represented by Formula (I) and its N-oxide, which includes specific substituents and structural elements, is used in a composition for effective arthropod control, potentially combined with other active ingredients like insecticides or repellents.
The compound provides effective control of harmful arthropods, offering improved efficacy in pest management.
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Abstract
Description
Heterocyclic compound and pest control composition containing the same
[0001] This application claims priority to and the benefit of Japanese Patent Application No. 2022-158626, filed on September 30, 2022, the entire contents of which are incorporated herein by reference. The present invention relates to a heterocyclic compound and an arthropod pest control composition containing the same.
[0002] Various compounds have been investigated so far for the purpose of controlling harmful arthropods. For example, Patent Document 1 describes that certain compounds have pest control effects.
[0003] International Publication No. 2016 / 129684
[0004] An object of the present invention is to provide a compound having excellent control activity against harmful arthropods.
[0005] The present invention is as follows: [1] A compound represented by formula (I) [Wherein, W represents an oxygen atom or a sulfur atom; R 1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group D, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group E, a phenyl group optionally substituted with one or more substituents selected from group F, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group F, C(O)R 4 , C(O)OR 4 , or C(O)NR 4 R 5 represents R 4 and R 5 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from group F, a 5- or 6-membered heterocyclic group optionally substituted with one or more substituents selected from group F, or a hydrogen atom; R 2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropyl group, a cyclopropylmethyl group, or NR 6 R 7represents R 6 and R 7 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, or R 6 and R 7 may be taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidyl group, n represents 0, 1, or 2, G 1 is a nitrogen atom or CR 3a represents 2 is a nitrogen atom or CR 3b represents 3 is a nitrogen atom or CR 3c represents 4 is a nitrogen atom or CR 3d represents R 3a , R 3b , R 3c and R 3d are the same or different and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group H, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group J, a phenyl group optionally substituted with one or more substituents selected from Group K, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group K, OR 8 , N.R. 8 R 9 , N.R. 8a R 9a , N.R. 10 NR 8 R 9 , N.R. 10 OR 9 , N.R. 9 C(O)R 11 , N.R. 10 NR 9 C(O)R 11 , N.R. 9 C(O)OR 12 , N.R. 10 NR 9 C(O)OR 12 , N.R. 9 C(O)NR 13 R14 , N.R. 10 NR 9 C(O)NR 13 R 14 , N=CHNR 13 R 14 , N=S(O) p R 15 R 16 , C(O)R 11 , C(O)OR 17 , C(O)NR 13 R 14 , C(O)NR 9 S (O) 2 R 18 , C.R. 19 = NOR 17 , N.R. 9 CR 10 = NOR 17 , S(O) m R 18 , a cyano group, a nitro group, a hydrogen atom, or a halogen atom; p represents 0 or 1; m represents 0, 1, or 2; R 8 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group M, a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group J 2 a phenyl group optionally substituted with one or more substituents selected from group J 2 a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a hydrogen atom and S(O) 2 R 18 represents R 11 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, Group J 2 a phenyl group optionally substituted with one or more substituents selected from group J 2 R represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 12represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group is selected from the group J 2 R may be substituted with one or more substituents selected from the following 13 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group M, S(O) 2 R 18 or a hydrogen atom, R 15 and R 16 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms; R 17 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 2 R represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of 18 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a group J 2 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of 19 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 20 , N.R. 21 R 22 or a hydrogen atom, R 20 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R 9 , R 10 , R 21 and R 22 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 8a and R9a together with the nitrogen atom to which they are bonded, form a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from group P, and Q is Q 1 or Q 2 represents Z 1 is NR 3j , an oxygen atom or a sulfur atom; Z 2 is NR 3k , an oxygen atom, or a sulfur atom; 1 and Z 1 NR 3j When expressing 1 is a nitrogen atom or CR 3e represents X 2 is a nitrogen atom or CR 3f represents X 3 is a nitrogen atom or CR 3g represents Q 1 and Z 1 When represents an oxygen atom, X 1 is a nitrogen atom or CR 3e represents X 2 is a nitrogen atom or CR 3f represents X 3 is a nitrogen atom or CR 3g (where X exists) 1 , X 2 and X 3 do not all represent nitrogen atoms), and Q is Q 1 and Z 1 represents a sulfur atom, X 1 is a nitrogen atom or CR 3e represents X 2 is a nitrogen atom or CR 3f represents X 3 is a nitrogen atom or CR 3g (where X exists) 1 , X 2 and X 3 do not all represent nitrogen atoms), and Q is Q 2 and Z 2 NR 3k When expressing 1 is a nitrogen atom or CR 3e represents X 2is a nitrogen atom or CR 3f represents X 4 is a nitrogen atom or CR 3h represents Q 2 and Z 2 When represents an oxygen atom, X 1 is a nitrogen atom or CR 3e represents X 2 is a nitrogen atom or CR 3f represents X 4 is a nitrogen atom or CR 3h (where X exists) 1 , X 2 and X 4 do not all represent nitrogen atoms), and Q is Q 2 and Z 2 represents a sulfur atom, X 1 is a nitrogen atom or CR 3e represents X 2 is a nitrogen atom or CR 3f represents X 4 is a nitrogen atom or CR 3h (where X exists) 1 , X 2 and X 4 Not all of R represent nitrogen atoms), 3j represents a methyl group which may be substituted with one or more substituents selected from Group T, a C2-C4 chain hydrocarbon group which may be substituted with one or more substituents selected from Group U, a C5-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group V, a group selected from Group K 2 a C3-C7 cycloalkyl group optionally substituted by one or more substituents selected from Group X; a phenyl group optionally substituted by one or more substituents selected from Group X; a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from Group X; C(O)R 23 , C(O)OR 24 , C(O)NR 25 R 26 , C(O)NR 27 S (O) 2 R 28 , C.R. 29 = NOR 24 , or S(O) k R 28k represents 0, 1 or 2; R 23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group X, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group X, or a hydrogen atom; R 24 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group X, or a hydrogen atom; R 25 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 26 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group V; 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of S(O) v R 28 or a hydrogen atom, v represents 0, 1 or 2, R 28 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more substituents selected from Group X, 29 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 30 , N.R. 31 R 32 or a hydrogen atom, R 30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R 27 , R 31 and R 32 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 3k represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group Y; 2C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from Group A 2 a phenyl group optionally substituted with one or more substituents selected from Group A 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of C(O)R 52 , C(O)OR 53 , C(O)NR 54 R 55 , C(O)NR 56 S (O) 2 R 57 , C.R. 58 = NOR 53 , S(O) t R 57 or a hydrogen atom, t represents 0, 1 or 2, R 52 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, Group A 2 a phenyl group optionally substituted with one or more substituents selected from Group A 2 R represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 53 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 2 R represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of 54 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 55 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group Y; 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of S(O) y R 28 or a hydrogen atom, y represents 0, 1 or 2, R 57 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a group A 2R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of 58 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 59 , N.R. 60 R 61 or a hydrogen atom, R 59 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R 56 , R 60 and R 61 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 3e , R 3f , R 3g and R 3h are the same or different, and group B 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E 2 a phenyl group optionally substituted with one or more substituents selected from Group E 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR 33 , N.R. 33 R 34 , N.R. 33a R 34a , N.R. 35 NR 33 R 34 , N.R. 35 OR 34 , N.R. 34 C(O)R 36 , N.R. 35 NR 34 C(O)R 36 , N.R. 34 C(O)OR 37 , N.R. 35 NR 34 C(O)OR 37 , N.R. 34 C(O)NR 38 R 39 , N.R. 35 NR 34 C(O)NR 38 R39 , N=CHNR 38 R 39 , N=S(O) q R 40 R 41 , C(O)R 36 , C(O)OR 42 , C(O)NR 38 R 39 , C(O)NR 34 S (O) 2 R 43 , C.R. 44 = NOR 42 , N.R. 34 CR 35 = NOR 42 , S(O) r R 43 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; q represents 0 or 1; r represents 0, 1, or 2; R 33 is Group B 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group D 2 a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group E 2 a phenyl group optionally substituted with one or more substituents selected from Group E 2 a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a hydrogen atom and S(O) 2 R 43 represents R 36 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, Group E 2 a phenyl group optionally substituted with one or more substituents selected from Group E 2 R represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 37represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group is selected from the group E 2 R may be substituted with one or more substituents selected from the following 38 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 39 is Group B 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of S(O) 2 R 43 or a hydrogen atom, R 40 and R 41 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms; R 42 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 2 R represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of 43 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a group E 2 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of 44 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 45 , N.R. 46 R 47 or a hydrogen atom, R 45 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R 34 , R 35 , R 46 and R 47are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 33a and R 34a together with the nitrogen atom to which they are attached, form the group F 2 Group D: a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, Group L 2 a phenyl group optionally substituted with one or more substituents selected from the group L 2Group E: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, and a halogen atom. Group F: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl optionally substituted with one or more halogen atoms)amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. Group H: a group consisting of C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl groups optionally substituted with one or more halogen atoms, cyano groups, hydroxy groups, and halogen atoms.Group J: a group consisting of C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, halogen atoms, oxo groups, hydroxy groups, cyano groups, and nitro groups. Group K: C1-C6 alkyl groups optionally substituted with one or more halogen atoms. Group J. 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR 49 , N.R. 48 R 49 , C(O)R 49 , C(O)NR 48 R 49 , O.C.(O.)R 48 , OC(O)OR 48 , N.R. 49 C(O)R 48 , N.R. 49 C(O)OR 48 , C(O)OR 49 , a halogen atom, a nitro group, a cyano group, and an amino group. 48 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R 49 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. Group L: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, Group J: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, 2 a phenyl group optionally substituted with one or more substituents selected from group J 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms; 2 a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of an amino group, NHR 50 , N.R. 50 R 51, a halogen atom, and a cyano group. 50 and R 51are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms. Group M: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, and a cyano group. Group P: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group. Group T: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a fluorine atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, and a halogen atom. Group U: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a fluorine atom and a C1-C3 alkyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a sulfanyl group, and a fluorine atom.Group V: the group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom. Group X: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl optionally substituted with one or more halogen atoms)amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom.Group Y: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom. Group A. 2 Group B: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl optionally substituted with one or more halogen atoms)amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. 2Group D: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a C1-C3 alkyl group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, a cyano group, and a halogen atom. 2 Group E: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, and a halogen atom. 2 Group F: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl optionally substituted with one or more halogen atoms)amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. 2Group H: a group consisting of C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, halogen atoms, oxo groups, hydroxy groups, cyano groups, and nitro groups. 2 Group J: a group consisting of C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, and halogen atoms. 2 : a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, an amino group, NHR 50 , N.R. 50 R 51 , C(O)R 50 , O.C.(O.)R 50 , C(O)OR 50 a group consisting of a cyano group, a nitro group, and a halogen atom; 2 Group L: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, and a fluorine atom. 2Group M: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl optionally substituted with one or more halogen atoms)amino group, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. 2 [2] a compound represented by the formula (I) (hereinafter referred to as Compound N of the present invention) or an N-oxide thereof (hereinafter referred to as Compound N of the present invention). [2] G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d [3] The compound according to [1] or an N-oxide thereof, 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d [4] The compound according to [1] or an N-oxide thereof, wherein Q is Q 1and Q 1 In this case, Z 1 , X 1 , X 2 and X 3 The combination is Z 1 is an oxygen atom, and X 1 is a nitrogen atom, and X 2 is CR 3f and X 3 is CR 3g A combination in which: Z 1 is an oxygen atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g A combination in which: Z 1 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 3 is a nitrogen atom; 1 is a sulfur atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g A combination in which: Z 1 is a sulfur atom, and X 1 is a nitrogen atom, and X 2 is CR 3f and X 3 is CR 3g A combination in which: Z 1 NR 3j and X 1 is a nitrogen atom, and X 2 is CR 3f and X 3 is CR 3g A combination in which: Z 1 NR 3j and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g or a combination in which Z 1 NR 3j and X 1 is CR3e and X 2 is CR 3f and X 3 [5] The compound or N-oxide thereof according to any one of [1] to [3], wherein Q is a nitrogen atom. 2 and Q 2 In this case, Z 2 , X 1 , X 2 and X 4 The combination is Z 2 is an oxygen atom, and X 1 is a nitrogen atom, and X 2 is CR 3f and X 4 is CR 3h A combination in which: Z 2 is an oxygen atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h A combination in which: Z 2 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom; 2 NR 3k and X 1 is a nitrogen atom, and X 2 is CR 3f and X 4 is CR 3h A combination in which: Z 2 NR 3k and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h A combination in which: Z 2 NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom; 2 NR 3k and X1 is CR 3e and X 2 is CR 3f and X 4 is CR 3h or a combination in which Z 2 NR 3k and X 1 is a nitrogen atom, and X 2 is a nitrogen atom, and X 4 is CR 3h [6] The compound or N-oxide thereof according to any one of [1] to [3], wherein R 2 is an ethyl group. [7] The compound or N-oxide thereof according to any one of [1] to [6], wherein W is an oxygen atom. [8] A composition for controlling arthropod pests, comprising the compound or N-oxide thereof according to any one of [1] to [7]. [9] A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound or N-oxide thereof according to any one of [1] to [7]: Group (a): a group consisting of insecticidal active components, acaricidal active components, and nematicidal active components; Group (b): fungicidal active components; Group (c): plant growth regulator components; Group (d): repellent components.
[10] A method for controlling arthropod pests, comprising applying an effective amount of the compound or N-oxide thereof according to any one of [1] to [7], or an effective amount of the composition according to [9], to arthropod pests or to a habitat of arthropod pests.
[11] A seed or a vegetative reproductive organ carrying an effective amount of the compound or N-oxide thereof according to any one of [1] to [7], or an effective amount of the composition according to [9].
[12] A compound represented by formula (II) [wherein the symbols have the same meanings as in [1]] or a salt thereof (hereinafter, the compound represented by formula (II) or a salt thereof will be referred to as intermediate A).
[0006] According to the present invention, arthropod pests can be controlled.
[0007] The substituents used in the present invention will be explained. A halogen atom refers to a fluorine atom, chlorine atom, bromine atom, or iodine atom. When a substituent is substituted with two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different. In this specification, the notation "CX-CY" means that the number of carbon atoms is X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 to 6. The chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl. Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy. Examples of alkenyloxy groups include 2-propenyloxy groups, 2-butenyloxy groups, and 5-hexenyloxy groups. Examples of alkynyloxy groups include 2-propynyloxy groups, 2-butynyloxy groups, and 5-hexynyloxy groups.
[0008] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups. Examples of cycloalkenyl groups include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl groups.
[0009] The 3- to 7-membered non-aromatic heterocyclic group represents 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 isoxazolidine 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. A 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group P, Group F 2 a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group H 2 Examples of the 3- to 7-membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from the following include the groups shown below. The 5- or 6-membered aromatic heterocyclic group refers to a 5- or 6-membered aromatic heterocyclic group, such as a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, or a thiadiazolyl group, and the 6-membered aromatic heterocyclic group refers to a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group. The 5- or 6-membered heterocyclic group represents a 5- or 6-membered aromatic heterocyclic group or a 5- or 6-membered non-aromatic heterocyclic group, and examples thereof include a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, and a pyrazinyl group. Examples of the (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms include a cyclopropylmethyl group, a (2-fluorocyclopropyl)methyl group, a cyclopropyl(fluoro)methyl group, and a (2-fluorocyclopropyl)(fluoro)methyl group. Phenyl C1-C3 alkyl groups {the phenyl moiety in the phenyl C1-C3 alkyl group is selected from the group J} 2 or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group may be selected from the group E 2Examples of the alkylsulfanyl group include a benzyl group, a 2-fluorobenzyl group, a 4-chlorobenzyl group, a 4-(trifluoromethyl)benzyl group, and a 2-[4-(trifluoromethyl)phenyl]ethyl group. Examples of alkylsulfanyl groups include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group. Examples of alkylsulfinyl groups include a methylsulfinyl group, an ethylsulfonyl group, a propylsulfinyl group, and an isopropylsulfinyl group. Examples of alkylsulfonyl groups include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group. Examples of alkylamino groups include a methylamino group, an ethylamino group, an isopropylamino group, and a hexylamino group. Examples of dialkylamino groups include a dimethylamino group, an ethylmethylamino group, an isopropylmethylamino group, and a dihexylamino group. Examples of alkylcarbonyl groups include acetyl, propanoyl, 2-methylpropanoyl, and hexanoyl groups. Examples of alkoxycarbonyl groups include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, and pentyloxycarbonyl groups.
[0010] Examples of the N-oxide of the compound of formula (I) include the compounds of the following formula: [In the formula, the symbols have the same meanings as defined above.]
[0011] The compound of the present invention and intermediate A may exist as one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, and geometric isomers. The compound of the present invention and intermediate A include each stereoisomer and a mixture of stereoisomers in any ratio.
[0012] The compound of the present invention and the compound represented by formula (II) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid. The acid addition salt can be obtained by mixing the compound of the present invention or the compound represented by formula (II) with an acid.
[0013] The following compounds are examples of the compound N of the present invention.
[0014] [Embodiment 1] In the compound N of the present invention, R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group D. [Embodiment 2] In compound N of the present invention, R 1 is a C1-C6 alkyl group. 1 is a methyl group. [Embodiment 4] In the compound N of the present invention, R 2 is a C1-C6 alkyl group. 2 is an ethyl group. [Embodiment 6] In the compound N of the present invention, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are bonded to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Embodiment 8] A compound of the present invention N in which W is an oxygen atom. [Embodiment 9] A compound of the present invention N in which G 1 , G 2 , G 3 , and G 4 The combination of 1 is CR 3a and G 2 is CR 3b and G 3is CR 3c and G 4 is a nitrogen atom; G 1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom, and G 4 is CR 3d A combination in which: 1 is CR 3a and G 2 is a nitrogen atom, and G 3 is CR 3c and G 4 is CR 3d A combination in which: 1 is a nitrogen atom, and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d or a combination in which 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d is a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a phenyl group optionally substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more halogen atoms, or a halogen atom. [Embodiment 10] A compound in which, in compound N of the present invention, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c, and R 3d is a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d is a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. 1 , G 2 , G 3 , and G 4 The combination of 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom; G 1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom, and G 4 is CR 3d A combination in which: 1 is CR 3a and G 2 is a nitrogen atom, and G 3 is CR 3c and G 4 is CR 3d A combination in which: 1 is a nitrogen atom, and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d or a combination in which 1 is CR 3a and G2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3b , and R 3d is a hydrogen atom, and R 3c is a halogen atom. [Embodiment 13] In the compound N of the present invention, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3b , and R 3d is a hydrogen atom, and R 3c is a halogen atom. [Embodiment 14] In the compound N of the present invention, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3b , and R 3d is a hydrogen atom, and R 3c is a halogen atom. 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 16] A compound according to aspect 5, wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 17] A compound according to aspect 6, wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 18] A compound according to aspect 7, wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 19] A compound according to Aspect 8, wherein R 1is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 20] In Aspect 9, R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 21] A compound according to Aspect 10, wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 22] A compound according to Aspect 11, wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 23] A compound according to Aspect 12, wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 24] A compound according to Aspect 13, wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 25] A compound according to Aspect 14, wherein R 1 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D. [Aspect 26] A compound according to Aspect 4, wherein R 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group. 1 is a C1-C6 alkyl group.1 is a C1-C6 alkyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 1 is a methyl group. 2 is a C1-C6 alkyl group. 2 is a C1-C6 alkyl group. 2 is a C1-C6 alkyl group. 2 is a C1-C6 alkyl group. 2 is a C1-C6 alkyl group. 2 is a C1-C6 alkyl group. 2 is a C1-C6 alkyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 2 NR 6 R 7 and R 6 and R 7and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 2 NR 6 R 7 and R 6 and R 7 together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect 76] A compound in Aspect 9, in which W is an oxygen atom. [Aspect 77] A compound in Aspect 10, in which W is an oxygen atom. [Aspect 78] A compound in Aspect 11, in which W is an oxygen atom. [Aspect 79] A compound in Aspect 12, in which W is an oxygen atom. [Aspect 80] A compound in Aspect 13, in which W is an oxygen atom. [Aspect 81] A compound in Aspect 14, in which W is an oxygen atom. [Aspect 82] In the compound N of the present invention, R 1 is a C1-C6 alkyl group, and R 2 is an ethyl group. [Embodiment 83] In the compound N of the present invention, R 1 is a C1-C6 alkyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 1 is a methyl group, and R 2 is an ethyl group. [Embodiment 87] In the compound N of the present invention, R 1 is a methyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a C1-C6 alkyl group, and R 2 NR6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are bonded to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 1 is a C1-C6 alkyl group, and R 2 is an ethyl group. 1 is a C1-C6 alkyl group, and R 2 is an ethyl group. 1 is a C1-C6 alkyl group, and R 2is an ethyl group. 1 is a C1-C6 alkyl group, and R 2 is an ethyl group. 1 is a C1-C6 alkyl group, and R 2 is an ethyl group. 1 is a C1-C6 alkyl group, and R 2 is an ethyl group. 1 is a C1-C6 alkyl group, and R 2 is an ethyl group. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group and W is an oxygen atom. 1 is a methyl group, and R 2 is an ethyl group. 1 is a methyl group, and R 2is an ethyl group. 1 is a methyl group, and R 2 is an ethyl group. 1 is a methyl group, and R 2 is an ethyl group. 1 is a methyl group, and R 2 is an ethyl group. 1 is a methyl group, and R 2 is an ethyl group. 1 is a methyl group, and R 2 is an ethyl group. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 1 is a methyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom.2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is a C1-C6 alkyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 2 is an ethyl group and W is an oxygen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group.1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a C1-C6 alkyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group.1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 1 is a methyl group, and R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are bonded to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are bonded to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 1 and Z 1 , X 1 , X 2 and X 3 The combination is Z 1 is an oxygen atom, and X 1 is a nitrogen atom, and X 2 is CR 3f and X 3 is CR 3g A combination in which: Z 1 is an oxygen atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g A combination in which: Z 1 is an oxygen atom, and X 1 is CR 3e and X 2is CR 3f and X 3 is a nitrogen atom; 1 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 3 is CR 3g A combination in which: Z 1 NR 3j and X 1 is a nitrogen atom, and X 2 is CR 3f and X 3 is CR 3g A combination in which: Z 1 NR 3j and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g or a combination in which Z 1 NR 3j and X 1 is CR 3e and X 2 is CR 3f and X 3 is a nitrogen atom; and R 3e is a hydrogen atom, R 3f and R 3g are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom, and R 3j is a methyl group optionally substituted with one or more halogen atoms, a C2-C4 alkyl group optionally substituted with one or more fluorine atoms, a C5-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Embodiment 193] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 2 and Z 2 , X 1 , X 2 and X 4 The combination is Z 2 is an oxygen atom, and X 1 is a nitrogen atom, and X2 is CR 3f and X 4 is CR 3h a combination in which Z is an oxygen atom and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h A combination in which: Z 2 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom; 2 NR 3k and X 1 is a nitrogen atom, and X 2 is CR 3f and X 4 is CR 3h A combination in which: Z 2 NR 3k and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h A combination in which: Z 2 NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom; or Z is NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4 is CR 3h and R 3e and R 3h are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, OR 33 , a hydrogen atom, or a halogen atom; R 3kis a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Embodiment 194] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 1 and Z 1 , X 1 , X 2 and X 3 The combination is Z 1 is an oxygen atom, and X 1 is a nitrogen atom, and X 2 is CR 3f and X 3 is CR 3g A combination in which: Z 1 is an oxygen atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g A combination in which: Z 1 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 3 is a nitrogen atom; or Z 1 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 3 is CR 3g and R 3e is a hydrogen atom, R 3f and R 3g and are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Embodiment 195] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 1 and Z 1 , X 1 , X 2 and X 3 The combination is Z 1 NR 3j and X 1 is a nitrogen atom, and X 2 is CR3f and X 3 is CR 3g A combination in which: Z 1 NR 3j and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g or a combination in which Z 1 NR 3j and X 1 is CR 3e and X 2 is CR 3f and X 3 is a nitrogen atom, and R 3e is a hydrogen atom, and R 3f and R 3g are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom, and R 3j is a methyl group optionally substituted with one or more halogen atoms, a C2-C4 alkyl group optionally substituted with one or more fluorine atoms, a C5-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Embodiment 196] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 2 and Z 2 , X 1 , X 2 and X 4 The combination is Z 2 is an oxygen atom, and X 1 is a nitrogen atom, and X 2 is CR 3f and X 4 is CR 3h A combination in which: Z 2 is an oxygen atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h or a combination in which Z 2 is an oxygen atom, and X 1 is CR 3e and X2 is CR 3f and X 4 is a nitrogen atom, and R 3e and R 3h are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 3f and are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Embodiment 197] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 2 and Z 2 , X 1 , X 2 and X 4 The combination is Z 2 NR 3k and X 1 is a nitrogen atom, and X 2 is CR 3f and X 4 is CR 3h A combination in which: Z 2 NR 3k and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h A combination in which: Z 2 NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom; or Z 2 NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4 is CR 3h and R 3e and R 3h are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 3fis a C1-C6 alkyl group optionally substituted with one or more halogen atoms, OR 33 , a hydrogen atom, or a halogen atom. [Embodiment 198] In any one of Embodiments 1 to 191 or the compound N of the present invention, Q is Q 2 and Z 2 , X 1 , X 2 and X 4 The combination is Z 2 NR 3k and X 1 is a nitrogen atom, and X 2 is CR 3f and X 4 is CR 3h A combination in which: Z 2 NR 3k and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h or a combination in which Z 2 NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom; or Z 2 NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4 is CR 3h and R 3e and R 3h are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Embodiment 199] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 1 and Z 1 NR 3j and X 1 is CR 3e and X2 is CR 3f and X 3 is a nitrogen atom, and R 3e is a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom, and R 3j is a methyl group optionally substituted with one or more halogen atoms, a C2-C4 alkyl group optionally substituted with one or more fluorine atoms, a C5-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Embodiment 200] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 1 and Z 1 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 3 is a nitrogen atom, and R 3e is a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Embodiment 201] A compound in any one of Embodiments 1 to 191 or compound N of the present invention, wherein Q is Q 1 Z is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 3 is CR 3g and R 3e and R 3f is a hydrogen atom, and R 3g is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Embodiment 202] A compound in any one of Embodiments 1 to 191 or compound N of the present invention, wherein Q is Q 2 and Z 2 NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4is a nitrogen atom, and R 3e is a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom, and R 3k is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Embodiment 203] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 2 and Z is NR 3j and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h and R 3e and R 3h is a hydrogen atom, and R 3j is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Embodiment 204] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 2 and Z 2 is an oxygen atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h and R 3e and R 3h and are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Embodiment 205] A compound in any one of Embodiments 1 to 191 or Compound N of the present invention, wherein Q is Q 2 and Z 2 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom, and R 3e is a hydrogen atom, and R 3fis a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Embodiment 206] A compound in any one of Embodiments 1 to 191 or compound N of the present invention, wherein Q is Q 1 and Z 1 is a sulfur atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g and R 3e is a hydrogen atom, and R 3g is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Embodiment 207] A compound according to any one of embodiments 1 to 191 or compound N of the present invention, wherein Q is Q 1 and Z 1 is a sulfur atom, and X 1 is a nitrogen atom, and X 2 is CR 3f and X 3 is CR 3g and R 3e is a hydrogen atom, and R 3g is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom.
[0015] Examples of the compound represented by formula (II) (hereinafter also referred to as intermediate C) include the following compounds.
[0016] [Aspect C1] In intermediate C, R 2 is a C1-C6 alkyl group. [Aspect C2] In intermediate C, R 2 is an ethyl group. [Aspect C3] In intermediate C, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. 2 NR 6 R 7 and R 6 and R 7are taken together with the nitrogen atom to which they are bonded to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect C5] A compound in intermediate C where W is an oxygen atom. [Aspect C6] A compound in intermediate C where G 1 , G 2 , G 3 , and G 4 The combination of 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom; G 1 is CR 3a and G 2 is CR 3b and G 3 is a nitrogen atom, and G 4 is CR 3d A combination in which: 1 is CR 3a and G 2 is a nitrogen atom, and G 3 is CR 3c and G 4 is CR 3d A combination in which: 1 is a nitrogen atom, and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d or a combination in which 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d is a hydrogen atom, and R 3bis a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a phenyl group optionally substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect C7] A compound in which, in intermediate C, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3c , and R 3d is a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3c , and R 3d is a hydrogen atom, and R 3b is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. 1 , G 2 , G 3 , and G 4 The combination of 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom; G 1 is CR 3a and G 2 is CR 3b and G3 is a nitrogen atom, and G 4 is CR 3d A combination in which: 1 is CR 3a and G 2 is a nitrogen atom, and G 3 is CR 3c and G 4 is CR 3d A combination in which: 1 is a nitrogen atom, and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d or a combination in which 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3b , and R 3d is a hydrogen atom, and R 3c is a halogen atom. [Aspect C10] A compound in which, in intermediate C, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is a nitrogen atom or CR 3d and R 3a , R 3b , and R 3d is a hydrogen atom, and R 3c is a halogen atom. [Aspect C11] A compound in which, in intermediate C, G 1 is CR 3a and G 2 is CR 3b and G 3 is CR 3c and G 4 is CR 3d and R 3a , R 3b , and R 3d is a hydrogen atom, and R3c is a halogen atom. [Aspect C12] A compound in intermediate C, wherein n is 0. [Aspect C13] A compound in aspect C1, wherein n is 0. [Aspect C14] A compound in aspect C2, wherein n is 0. [Aspect C15] A compound in aspect C3, wherein n is 0. [Aspect C16] A compound in aspect C4, wherein n is 0. [Aspect C17] A compound in aspect C5, wherein n is 0. [Aspect C18] A compound in aspect C6, wherein n is 0. [Aspect C19] A compound in aspect C7, wherein n is 0. [Aspect C20] A compound in aspect C8, wherein n is 0. [Aspect C21] A compound in aspect C9, wherein n is 0. [Aspect C22] A compound in aspect C10, wherein n is 0. [Aspect C23] A compound in aspect C11, wherein n is 0. [Aspect C24] A compound in aspect C5, wherein R 2 is a C1-C6 alkyl group. [Aspect C25] In Aspect C6, R 2 is a C1-C6 alkyl group. [Aspect C26] In Aspect C7, R 2 is a C1-C6 alkyl group. [Aspect C27] A compound in Aspect C8, wherein R 2 is a C1-C6 alkyl group. [Aspect C28] In Aspect C9, R 2 is a C1-C6 alkyl group. [Aspect C29] In Aspect C10, R 2 is a C1-C6 alkyl group. [Aspect C30] In Aspect C11, R 2 is a C1-C6 alkyl group. [Aspect C31] A compound in Aspect C5, wherein R 2 is an ethyl group. [Aspect C32] A compound according to Aspect C6, wherein R 2 is an ethyl group. [Aspect C33] A compound according to Aspect C7, wherein R 2 is an ethyl group. [Aspect C34] A compound according to Aspect C8, wherein R 2 is an ethyl group. [Aspect C35] A compound according to Aspect C9, wherein R 2 is an ethyl group. [Aspect C36] A compound according to Aspect C10, wherein R 2 is an ethyl group. [Aspect C37] A compound according to Aspect C11, wherein R 2is an ethyl group. [Aspect C38] In Aspect C5, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect C39] In Aspect C6, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect C40] In Aspect C7, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect C41] A compound in Aspect C8, wherein R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect C42] In Aspect C9, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect C43] A compound in Aspect C10, wherein R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect C44] A compound in Aspect C11, wherein R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect C45] In Aspect C5, R 2 NR 6 R 7 and R 6and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect C46] In Aspect C6, R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect C47] In Aspect C7, R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect C48] In Aspect C8, R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect C49] In Aspect C9, R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect C50] In Aspect C10, R 2 NR 6 R 7 and R 6 and R 7 and together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect C51] In Aspect C11, R 2 NR 6 R 7 and R 6 and R 7together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group. [Aspect C52] A compound in Aspect C6, in which W is an oxygen atom. [Aspect C53] A compound in Aspect C7, in which W is an oxygen atom. [Aspect C54] A compound in Aspect C8, in which W is an oxygen atom. [Aspect C55] A compound in Aspect C9, in which W is an oxygen atom. [Aspect C56] A compound in Aspect C10, in which W is an oxygen atom. [Aspect C57] A compound in Aspect C11, in which W is an oxygen atom. [Aspect C58] A compound in Aspect C6, in which R 2 is an ethyl group and W is an oxygen atom. [Aspect C59] A compound in which R 2 is an ethyl group and W is an oxygen atom. [Aspect C60] A compound in which R 2 is an ethyl group and W is an oxygen atom. [Aspect C61] A compound in which R 2 is an ethyl group and W is an oxygen atom. [Aspect C62] A compound in which R 2 is an ethyl group and W is an oxygen atom. [Aspect C63] A compound in which R 2 is an ethyl group and W is an oxygen atom. [Aspect C64] A compound in which R 2 is an ethyl group and W is an oxygen atom. [Aspect C65] A compound in which R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. [Aspect C66] In Aspect C7, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. [Aspect C67] A compound in which R 2 NR 6 R 7 and R 6 and R 7are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. [Aspect C68] In Aspect C9, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. [Aspect C69] A compound in which R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. [Aspect C70] In Aspect C11, R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. [Aspect C71] A compound in which R 2 NR 6 R 7 and R 6 and R 7 are the same or different and are a C1-C6 alkyl group or a hydrogen atom, and W is an oxygen atom. [Aspect C72] In Aspect C6, R 2 NR 6 R 7 and R 6 and R 7 and R are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7and R 6 and R 7 and R are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. [Aspect C76] A compound in which R 2 NR 6 R 7 and R 6 and R 7 and R are taken together with the nitrogen atom to which they are bonded to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 and R are taken together with the nitrogen atom to which they are attached to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 NR 6 R 7 and R 6 and R 7 are taken together with the nitrogen atom to which they are bonded to form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidinyl group, and W is an oxygen atom. 2 is an ethyl group and n is 0. [Aspect C80] A compound in which R 2 is an ethyl group and n is 0. [Aspect C81] A compound in which R 2 is an ethyl group and n is 0. [Aspect C82] A compound in which R 2 is an ethyl group and n is 0. [Aspect C83] In Aspect C9, R2 is an ethyl group and n is 0. [Aspect C84] A compound in which R 2 is an ethyl group and n is 0. [Aspect C85] A compound in which R 2 is an ethyl group, and n is 0. [Aspect C86] A compound in Aspect C1, in which W is an oxygen atom, and n is 0. [Aspect C87] A compound in Aspect C2, in which W is an oxygen atom, and n is 0. [Aspect C88] A compound in Aspect C3, in which W is an oxygen atom, and n is 0. [Aspect C89] A compound in Aspect C4, in which W is an oxygen atom, and n is 0. [Aspect C90] A compound in Aspect C6, in which W is an oxygen atom, and n is 0. [Aspect C91] A compound in Aspect C7, in which W is an oxygen atom, and n is 0. [Aspect C92] A compound in Aspect C8, in which W is an oxygen atom, and n is 0. [Aspect C93] A compound in Aspect C9, in which W is an oxygen atom, and n is 0. [Aspect C94] A compound in Aspect C10, in which W is an oxygen atom, and n is 0. [Aspect C95] The compound of Aspect C11, wherein W is an oxygen atom and n is 0. [Aspect C96] The compound of Aspect C1 to Aspect C95 or Intermediate C, wherein Q is Q 1 and Z 1 NR 3j and X 1 is CR 3e and X 2 is CR 3f and X 3 is a nitrogen atom, and R 3e is a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom, and R 3j is a methyl group optionally substituted with one or more halogen atoms, a C2-C4 alkyl group optionally substituted with one or more fluorine atoms, a C5-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Aspect C97] A compound in any of Aspects C1 to C95 or Intermediate C, in which Q is Q 1 and Z 1 is an oxygen atom, and X1 is CR 3e and X 2 is CR 3f and X 3 is a nitrogen atom, and R 3e is a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Aspect C98] A compound in any of Aspects C1 to C95 or Intermediate C, wherein Q is Q 1 and Z 1 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 3 is CR 3g and R 3e and R 3f is a hydrogen atom, and R 3g is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Aspect C99] A compound in any of Aspects C1 to C95 or Intermediate C, wherein Q is Q 2 and Z 2 NR 3k and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom, and R 3e is a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom, and R 3k is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Aspect C100] A compound in any of Aspects C1 to C95 or Intermediate C, wherein Q is Q 2 and Z is NR 3j and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h and R3e and R 3h is a hydrogen atom, and R 3j is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms. [Aspect C101] A compound in any of Aspects C1 to C95 or Intermediate C, wherein Q is Q 2 and Z 2 is an oxygen atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 4 is CR 3h and R 3e and R 3h and are the same or different and are a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect C102] A compound in any of Aspects C1 to C95 or Intermediate C, wherein Q is Q 2 and Z 2 is an oxygen atom, and X 1 is CR 3e and X 2 is CR 3f and X 4 is a nitrogen atom, and R 3e is a hydrogen atom, and R 3f is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Aspect C103] A compound in any of Aspects C1 to C95 or Intermediate C, wherein Q is Q 1 and Z 1 is a sulfur atom, and X 1 is CR 3e and X 2 is a nitrogen atom, and X 3 is CR 3g and R 3e is a hydrogen atom, and R 3g is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom. [Aspect C104] A compound in any of Aspects C1 to C95 or Intermediate C, wherein Q is Q 1 and Z 1 is a sulfur atom, and X 1is a nitrogen atom, and X 2 is CR 3f and X 3 is CR 3g and R 3e is a hydrogen atom, and R 3g is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a hydrogen atom, or a halogen atom.
[0017] Next, the method for producing the compound of the present invention will be described.
[0018] Production Method 1 A compound represented by formula (I-b) (hereinafter referred to as compound (I-b)) or a compound represented by formula (I-c) (hereinafter referred to as compound (I-c)) can be produced by reacting a compound represented by formula (I-a) (hereinafter referred to as compound (I-a)) with an oxidizing agent. [In the formula, the symbols have the same meanings as defined above.]
[0019] First, a method for producing compound (I-b) from compound (I-a) will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); acetic acid; water; and mixtures of two or more of these. Examples of oxidizing agents used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be added as necessary. Examples of bases used in the reaction include sodium carbonate. When a base is used in the reaction, the base is usually used in a ratio of 0.01 to 1 mole per mole of compound (I-a). Examples of catalysts used in the reaction include tungstic acid and sodium tungstate. When a catalyst is used in the reaction, the catalyst is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (I-a). In the reaction, the oxidizing agent is typically used in a ratio of 1 to 1.2 moles per mole of compound (I-a). 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. After completion of the reaction, water is added to the reaction mixture, followed by extraction with an organic solvent. The organic layer is washed, as necessary, with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate). The organic layer is dried and concentrated to obtain compound (I-b).
[0020] Next, a method for producing compound (I-c) from compound (I-b) will be described. The reaction is typically 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 these. Examples of oxidizing agents used in the reaction include mCPBA and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be added as needed. Examples of bases used in the reaction include sodium carbonate. When a base is used in the reaction, the base is typically used in a ratio of 0.01 to 1 mole per mole of compound (I-b). Examples of catalysts used in the reaction include sodium tungstate. When a catalyst is used in the reaction, the catalyst is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (I-b). The oxidizing agent is typically used in a ratio of 1 to 2 moles per mole of compound (I-b). 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. After the reaction is complete, water is added to the reaction mixture, which is then extracted with an organic solvent. The organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate) as needed. Compound (I-c) can be obtained by drying and concentrating the organic layer.
[0021] Compound (I-c) can also be produced in a one-step reaction (one-pot) by reacting compound (I-a) with an oxidizing agent. The reaction can be carried out using the oxidizing agent in a proportion of usually 2 to 5 moles per mole of compound (I-a) in accordance with the method for producing compound (I-c) from compound (I-b).
[0022] Production Method 2 The compound represented by formula (I-1-A) (hereinafter referred to as compound (I-1-A)) can be produced by reacting a compound represented by formula (M1-1-A) (hereinafter referred to as compound (M1-1-A)) with a compound represented by formula (M2-1) (hereinafter referred to as compound (M2-1)) in the presence of a condensing agent. [In the formula, R Arepresents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group optionally substituted with one or more substituents selected from Group F, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group F, and the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers (hereinafter referred to as ethers) such as tetrahydrofuran (hereinafter referred to as THF) and methyl tert-butyl ether (hereinafter referred to as MTBE); halogenated hydrocarbons; aromatic hydrocarbons (hereinafter referred to as aromatic hydrocarbons) such as toluene and xylene; esters (hereinafter referred to as esters) such as ethyl acetate and butyl acetate; nitriles; aprotic polar solvents (hereinafter referred to as 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 (hereinafter referred to as nitrogen-containing aromatic compounds) such as pyridine, picoline, lutidine, and quinoline; and mixtures of two or more of these. Condensing agents used in the reaction include, for example, carbodiimides such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide. A catalyst can be used in the reaction, if necessary. An example of a catalyst used in the reaction is 1-hydroxybenzotriazole. When a catalyst is used in the reaction, the catalyst is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (M1-1-A). A base can be used in the reaction, if necessary. Examples of bases used in the reaction include organic bases such as triethylamine, N,N-diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine (hereinafter referred to as organic bases). When a base is used in the reaction, the base is typically used in a ratio of 1 to 2 moles per mole of compound (M1-1-A). In the reaction, the 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, relative to 1 mole of the compound (M1-1-A).The reaction temperature is usually in the range of 0 to 200°C. The reaction time is usually in the range of 0.1 to 12 hours. After completion of the reaction, compound (I-1-A) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. Compound (M2-1) is a commercially available compound or can be produced using known methods.
[0023] Production Method 3 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)). [In the formula, the symbols have the same meanings as above.] 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 these. A base can be used in the reaction as needed. Examples of bases used in the reaction 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 a base is used in the reaction, the base is usually used in a ratio of 1 to 2 moles per mole of compound (M1-1-A). In the reaction, the compound (M2-2) is usually used in a ratio of 0.8 to 1.2 moles per mole of compound (M1-1-A). The reaction temperature is usually in the range of −20 to 200°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (I-1-A) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M2-2) is a commercially available compound or can be produced by a known method.
[0024] Production Method 4 A compound represented by formula (I-2-B) (hereinafter referred to as compound (I-2-B)) can be produced by reacting a compound represented by formula (II) (hereinafter referred to as compound (II)) with a compound represented by formula (R-1) (hereinafter referred to as compound (R-1)) in the presence of a base. [In the formula, R B represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, C(O)R 4 , C(O)OR 4 , or C(O)NR 4 R 5 where L represents a leaving group such as a chlorine atom or a bromine atom, and the other symbols have the same meanings as above. 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 these. Examples of bases used in the reaction include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides), alkali metal carbonates, and organic bases. For the reaction, compound (R-1) is usually used in a ratio of 1 to 5 moles and base is usually used in a ratio of 1 to 2 moles per mole of compound (II). The reaction temperature is usually in the range of 0 to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (I-2-B) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment such as drying and concentrating the organic layer. Compound (R-1) is a commercially available compound or can be produced using known methods.
[0025] Production Method 5 A compound represented by formula (I-1) (hereinafter referred to as compound (I-1)) can be produced by reacting a compound represented by formula (M1-2) (hereinafter referred to as compound (M1-2)) with a compound represented by formula (M2-3) (hereinafter referred to as compound (M2-3)). [In the formula, V 1 represents a halogen atom, and the other symbols have the same meanings as above.]
[0026] V 1 When is a fluorine atom, compound (I-1) can be produced by reacting compound (M1-2) with compound (M2-3) in the presence of a base. 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 these. Examples of bases used in the reaction include alkali metal carbonates and alkali metal hydrides. For the reaction, compound (M2-3) is usually used in a ratio of 0.8 to 1.2 moles and a base is usually used in a ratio of 1 to 2 moles per mole of compound (M1-2). The reaction temperature is usually in the range of 0 to 200°C. The reaction time is usually in the range of 0.5 to 24 hours. After completion of the reaction, compound (I-1) can be obtained by adding water to the reaction mixture, extracting it with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
[0027] V 1When M is a chlorine atom, bromine atom, or iodine atom, compound (I-1) can be produced by reacting compound (M1-2) with compound (M2-3) in the presence of a base and a copper catalyst or a palladium catalyst. 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 these. Examples of bases used in the reaction 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. Examples of copper catalysts used in the reaction include copper(I) iodide, copper(I) bromide, copper(I) chloride, and copper(I) oxide. When a copper catalyst is used in the reaction, the copper catalyst is usually used in a ratio of 0.01 to 0.5 moles per mole of compound (M1-2). Examples of palladium catalysts used in the reaction include palladium(II) acetate and tris(dibenzylideneacetone)dipalladium(0). When a palladium catalyst is used in the reaction, the palladium catalyst is typically used in a ratio of 0.01 to 0.2 moles per mole of compound (M1-2). A ligand can be used in the reaction, if necessary. Examples of ligands used in the reaction include acetylacetone, salen, phenanthroline, triphenylphosphine, and 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene. When a ligand is used in the reaction, the ligand is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (M1-2). When a ligand is used in the reaction, the compound (M2-3) is typically used in a ratio of 0.8 to 1.2 moles, and the base is typically used in a ratio of 1 to 2 moles per mole of compound (M1-2). The reaction temperature is typically in the range of 0 to 200°C. The reaction time is usually in the range of 0.5 to 24 hours. After the reaction is completed, water is added to the reaction mixture, and the mixture is extracted with an organic solvent. The organic layer is then dried and concentrated, and other post-treatment procedures are carried out to obtain compound (I-1). 1 is R A or R BCompounds which are either commercially available compounds or can be prepared using known methods.
[0028] Production Method 6 Compound (Ia) can be produced according to the following scheme. [In the formula, X a represents a chlorine atom, a bromine atom, or an iodine atom; X b is SR 2 or a hydrogen atom, and other symbols have the same meanings as above.]
[0029] First, a process (hereinafter referred to as Process 6-A) for 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)) will be described. Compound (M3-1) can be produced by reacting compound (III-1) with a halogenating agent. 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 thereof. Examples of halogenating agents include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. In the reaction, the halogenating agent is usually used in a ratio of 1 to 20 moles per mole of compound (III-1). The reaction temperature is usually in the range of −20° C. to 200° C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is completed, water is added to the reaction mixture, and the mixture is extracted with an organic solvent, and the organic layer is dried and concentrated, whereby compound (M3-1) can be obtained by post-treatment.
[0030] Next, the process for producing compound (I-a) from compound (M3-1) will be described. Compound (I-a) can be produced 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. 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 these. Examples of metal catalysts used in the reaction include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases. A ligand 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 a ligand is used in the reaction, the ligand is typically used in a ratio of 0.01 to 1 mole per mole of compound (M3-1). In the reaction, compound (R-2) is usually used in a ratio of 1 to 20 moles, a metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and a base is usually used in a ratio of 0.1 to 5 moles, relative to 1 mole of compound (M3-1). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours.After the reaction is complete, compound (I-a) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer, etc. Compound (R-2) is known or can be produced according to known methods.
[0031] Next, the process for producing compound (I-a) from compound (III-1) will be described. Compound (I-a) can also be produced 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. 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 these. Examples of halogenating agents include bromine, iodine, sodium bromide, potassium bromide, sodium iodide, and potassium iodide. An oxidizing agent can be used in the reaction as needed. Examples of oxidizing agents used in the reaction include hydrogen peroxide, tert-butyl hydroperoxide, and DMSO. When an oxidizing agent is used in the reaction, the oxidizing agent is usually used in a ratio of 1 to 20 moles per mole of compound (III-1). In the reaction, 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 per mole of compound (III-1). The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (I-a) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. Compound (R-3) is known or can be produced by a known method.
[0032] Production Method 7 The compound represented by formula (IS) (hereinafter referred to as compound (IS)) can be produced by reacting compound (I-1) with a sulfating agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is carried out in a solvent or in the absence of a solvent. Examples of solvents include ethers, halogenated hydrocarbons, aromatic hydrocarbons, nitriles, nitrogen-containing aromatic compounds, and mixtures of two or more thereof. Examples of sulfurizing agents include diphosphorus pentasulfide and Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide). In the reaction, the sulfurizing agent is usually used in a ratio of 1 mole to 3 moles per mole of compound (I-1). The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 1 to 24 hours. After completion of the reaction, compound (IS) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
[0033] Production Method 8 The compound represented by formula (II-S) (hereinafter referred to as compound (II-S)) can be produced by reacting compound (II-O) with a sulfating agent. [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method 7, except that compound (II-O) is used in place of compound (I-1). The compound of formula (II-S-B) can be produced from compound (II-S) in accordance with Production Method 4. [In the formula, the symbols have the same meanings as defined above.]
[0034] The N-oxide of the compound of formula (I) can be produced by reacting the compound of formula (I) with an oxidizing agent. The reaction can be carried out, for example, in accordance with Production Method 1, the method described in U.S. Patent Application Publication No. 2018 / 0009778, or WO 2016 / 121970.
[0035] The methods for producing intermediates are described below.
[0036] Reference Production Method 1 A compound represented by formula (M1-1-D) (hereinafter referred to as compound (M1-1-D)) can be produced by reacting a compound represented by formula (M1-3) (hereinafter referred to as compound (M1-3)) with a compound represented by formula (R-5) (hereinafter referred to as compound (R-5)) in the presence of a base. [In the formula, R D represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, or a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, and the other symbols have the same meanings as above.] 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 these. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases. In the reaction, compound (R-5) is usually used in a ratio of 1 to 5 moles and a base is usually used in a ratio of 1 to 2 moles per mole of compound (M1-3). The reaction temperature is usually in the range of 0 to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (M1-1-D) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
[0037] Reference Production Method 2 Compound (M1-1-A) can be produced 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)). [In the formula, X drepresents a fluorine atom or a chlorine atom, and other symbols have the same meanings as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include aprotic polar solvents, alcohols, and mixtures of two or more of these. A base can be used in the reaction, if necessary. Examples of bases used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 moles per mole of compound (M1-2-2). The reaction is usually carried out in a ratio of 1 to 100 moles of compound (R-6) per mole of compound (M1-2-2). The reaction temperature is usually in the range of 25°C to 200°C. The reaction time is usually in the range of 0.1 to 48 hours. After completion of the reaction, compound (M1-1-A) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment such as drying and concentrating the organic layer. Compound (R-6) is a commercially available compound or can be produced using known methods.
[0038] Reference Production Method 3 The compound (M1-3) can be produced by reacting the compound (M1-2-2) with ammonia. [In the formula, the symbols have the same meanings as above.] 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 these. A base can be used in the reaction, if necessary. Examples of bases used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 moles per mole of compound (M1-2-2). Ammonia can also be used in the form of a solution such as aqueous ammonia or ammonia methanol solution. The reaction is usually used in a ratio of 1 to 100 moles per mole of compound (M1-2-2). The reaction temperature is usually in the range of -20°C to 100°C. The reaction time is usually in the range of 0.1 to 48 hours. After completion of the reaction, compound (M1-3) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
[0039] Reference Production Method 4: The compounds represented by formula (M1-2b) and formula (M1-2c) can be produced by reacting a compound represented by formula (M1-2a) (hereinafter referred to as compound (M1-2a)) with an oxidizing agent. The compound represented by formula (M1-2c) can also be produced by reacting a compound represented by formula (M1-2b) with an oxidizing agent. [wherein the symbols have the same meanings as defined above.] These reactions can be carried out in accordance with Production Method 1.
[0040] Reference Production Method 5 Compound (M1-2a) can be produced according to the following scheme. [In the formula, the symbols have the same meanings as defined above.]
[0041] These reactions can be carried out in accordance with Production Method 6. The compound represented by formula (M1-4) (hereinafter referred to as compound (M1-4)) is publicly known or can be produced in accordance with the methods described in WO 2015 / 157093, WO 2016 / 109706, ORganic & Biomolecula® ChemistRy, 2017, 15, 4199, and EuRoppian JouRnal of Medicinal ChemistRy, 2016, 123, 916, and the like.
[0042] Reference Production Method 6 Compound (II-O) can be produced by reacting compound (M1-3) with compound (M2-1) or compound (M2-2). [wherein the symbols have the same meanings as defined above.] These reactions can be carried out according to Production Method 2 or Production Method 3, using compound (M1-3) instead of compound (M1-1-A).
[0043] Reference Production Method 7 The compound represented by formula (M3-1-A) can be produced by reacting a compound represented by formula (M1-6-A) (hereinafter referred to as compound (M1-6-A)) with compound (M2-1) or compound (M2-2). [wherein the symbols have the same meanings as defined above.] These reactions can be carried out according to Production Method 2 or Production Method 3, except that compound (M1-6-A) is used in place of compound (M1-1-A).
[0044] Reference Production Method 8 The compound represented by formula (M1-6-D) (hereinafter referred to as compound (M1-6-D)) can be produced according to the following scheme. [In the formula, the symbols have the same meanings as defined above.]
[0045] First, a method for producing the compound represented by formula (M1-7) (hereinafter referred to as compound (M1-7)) will be described. Compound (M1-7) can be produced by reacting a compound represented by formula (M1-5) (hereinafter referred to as compound (M1-5)) with ammonia. The reaction can be carried out in accordance with Reference Production Method 3, using compound (M1-5) instead of compound (M1-2-2).
[0046] Next, a method for producing compound (M1-6-D) will be described. Compound (M1-6-D) can be produced by reacting compound (M1-7) with compound (R-5) in the presence of a base. The reaction can be carried out in accordance with Reference Production Method 1, using compound (M1-7) instead of compound (M1-3).
[0047] Reference Production Method 9 The compound (M1-6-A) can be produced according to the following scheme. [In the formula, the symbols have the same meanings as defined above.]
[0048] First, a method for producing the compound represented by formula (M1-8-A) (hereinafter referred to as compound (M1-8-A)) will be described. Compound (M1-8-A) can be produced by reacting compound (M1-4) with compound (R-6). The reaction can be carried out in accordance with Reference Production Method 2, using compound (M1-4) instead of compound (M1-2-2).
[0049] Next, a production method for compound (M1-6-A) will be described. Compound (M1-6-A) can be produced by reacting compound (M1-8-A) with a halogenating agent. The reaction can be carried out in accordance with step 6-A of production method 6, using compound (M1-8-A) instead of compound (III-1).
[0050] Reference Production Method 10 The compound represented by formula (M3-1-B) (hereinafter referred to as compound (M3-1-B)) can be produced according to the following scheme. [In the formula, the symbols have the same meanings as defined above.]
[0051] First, a method for producing the compound represented by formula (M3-2) (hereinafter referred to as compound (M3-2)) will be described. Compound (M3-2) can be produced by reacting compound (M1-7) with compound (M2-1) or compound (M2-2). This reaction can be carried out in accordance with Production Method 2 or Production Method 3, using compound (M1-7) instead of compound (M1-1-A).
[0052] Next, a method for producing compound (M3-1-B) will be described. Compound (M3-1-B) can be produced by reacting compound (M3-2) with compound (R-1) in the presence of a base. The reaction can be carried out in accordance with Production Method 4, using compound (M3-2) instead of compound (II).
[0053] Reference Production Method 11 The compound represented by formula (III-1-A) (hereinafter referred to as compound (III-1-A)) can be produced according to the following scheme. [wherein the symbols have the same meanings as defined above.] Compound (III-1-A) can be produced by reacting compound (M1-8-A) with compound (M2-1) or compound (M2-2). This reaction can be carried out in accordance with Production Method 2 or Production Method 3, using compound (M1-8-A) instead of compound (M1-1-A).
[0054] Reference Production Method 12 The compound represented by formula (III-1-B) (hereinafter referred to as compound (III-1-B)) can be produced according to the following scheme. [In the formula, the symbols have the same meanings as defined above.]
[0055] First, a method for producing a compound represented by formula (III-2-B) (hereinafter referred to as compound (III-2-B)) will be described. Compound (III-2-B) can be produced 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 in accordance with Production Method 2 or Production Method 3, using compound (M1-9) instead of compound (M1-1-A).
[0056] Next, a method for producing compound (III-1-B) will be described. Compound (III-1-B) can be produced by reacting compound (III-2-B) with compound (R-1) in the presence of a base. The reaction can be carried out according to Production Method 4, using compound (III-2-B) instead of compound (II).
[0057] Reference Production Method 13 The compound (M1-9) can be produced by reacting the compound (M1-4) with ammonia. [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Reference Production Method 3, except that compound (M1-4) is used in place of compound (M1-2-2).
[0058] The compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below (hereinafter referred to as the present component). The term "mixed or used in combination" means that the compound of the present invention and the present component are used simultaneously, separately, or with a time interval. When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate preparations or in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (i.e., the present component) and the compound of the present invention.
[0059] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, The group consisting of inhibitors of classes III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients, which are described in the IRAC mechanism-based classification.
[0060] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These are listed in the FRAC classification based on the mechanism of action.
[0061] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).
[0062] Group (d) is a group of repellent ingredients.
[0063] Examples of combinations of the present ingredient and the compound of the present invention are described below. For example, alanycarb + SX refers to a combination of alanycarb and SX. The abbreviation SX refers to any one of the present compounds selected from the compound group SX1 to SX1908. The present ingredients described below are all known ingredients and can be obtained from commercially available preparations or produced by known methods. When the present ingredient is a microorganism, it can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).
[0064] Combinations of the present ingredient of the above group (a) with the compound of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acinonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos-methyl + SX, azocyclotin + SX, Celastrus angulatus bark + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX, bioallethrin + SX,Bioresmethrin + SX, bistrifluron + SX, borax + SX, boric acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, cartap hydrochloride + SX, cartap + SX Chinomethionate + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin A A) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX,Cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, cyproflanilide + SX, cyromazine + SX, Dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, Dinotefuran + SX, disodium octaborate + SX, disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX,Dried leaves of Dryopteris filix (mas) + SX, emamectin benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethifencarb + SX, ethion + SX, ethiprole + SX, ethoprophos + SX, etofenprox + SX. Etoxazole + SX, Artemisia absinthium extract + SX, Azadirachta indica extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract + SX, Urtica dioica extract + SX, Viscum album extract + SX, Famphur + SX, Fenamiphos + SX Fenazaquin + SX,Fenbutatin oxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, Flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX,Furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, Imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX Kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX,Lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, Methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX, nicotine sulfate + SX, Nitenpyram + SX, Novaluron + SX, Noviflumuron + SX,Chenopodium anthelminticum seed oil + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX Pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, Pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX,Pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + 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 ambrosioides near ambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, Thiometon + SX, thiosultap disodium + SX, thiosultap monosodium + SX, tigolaner + SX, thioantraniliprole + SX, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, Triflumuron + SX, trimethacarb + SX,Tyclopyrazoflor + SX, umifoxolaner + SX, vamidothion + SX, Quassia amara wood extract + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + 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-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methanesulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX,2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, BT crop protein Cry1Ab (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 + SX, BT crop protein mCry3A + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 + SX, Adoxophyes orana granulovirus BV-0001 + SX, Anticarsia gemmatalis MNPV (multiple nucleocapsid nucleopolyhedrovirus) + SX, Autographa californica MNPV + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella GV strain V22 + SX, Cryptophlebia leucotreta GV + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera nucleopolyhedrovirus BV-0003 + SX, Helicoverpa zea ... NPV) + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX,Mamestra configurata nucleopolyhedrosis virus (NPV) + SX, Neodiprion abietis nucleopolyhedrosis virus (NPV) + SX, Neodiprion lecontei nucleopolyhedrosis virus (NPV) + SX, Neodiprion sertifer nucleopolyhedrosis virus (NPV) + SX, Nosema locustae + SX, Orgyia pseudotsugata nucleopolyhedrosis virus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX, Spodoptera exigua MNPV + SX, Spodoptera littoralis MNPV + SX, Spodoptera littoralis NPV + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b+ SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX,Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX,Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego 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, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinogensis strain A396 + SX,Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX,Wolbachia pipientis + SX。,
[0065] Combinations of the present ingredient of the above group (b) with the compound of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, Benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin S + SX, Bordeaux mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionate + SX, chitin + SX, chloroinconazide + SX, chloroneb + SX,Chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, copper oxychloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, Dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dicloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipymetitrone + SX, dithianon + SX,Dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX, dodemorph + SX, dodine + SX, edifenphos + SX, enoxastrobin + SX, epoxiconazole + SX, etaconazole + SX, ethaboxam + SX, ethirimol + SX, etridiazole + SX, garlic extract (Allium sativum) + SX, extract of the cotyledons of lupine plantlets (BLAD) + SX, horsetail extract (Equisetum arvense) + SX SX, tea tree extract (Melaleuca alternifolia) + SX, giant knotweed extract (Reynoutria sachalinensis) + SX, nasturtium extract (Tropaeolus majus) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, fenfuram + SX, fenhexamid + SX, fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX Fenpropidin + SX, Fenpropimorph + SX,Fenpyrazamine + SX, triphenyltin acetate + SX, triphenyltin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, Fosetyl + SX, fosetyl-aluminium + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + SX,Guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX Isofetamide + SX, isoflucipram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, oak leaves and bark of quercus + SX, mancozeb + SX, mandestrobin + SX, mandipropamid + SX, maneb + SX, mefentrifluconazole + SX, mepanipyrim + SX, Mepronil + SX, meptyldinocap + SX, metalaxyl + SX, metalaxyl-M + SX, metarylpicoxamid + SX,Metconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofurace + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, Oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, Potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX,Probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, Pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, quinoa saponins Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX,Simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX, thifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, Thymol + SX, tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, triforine + SX, triticonazole + SX, Validamycin + SX, valifenalate + SX, vinclozolin + SX,マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(zoxamide) + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N '-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX,4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R,5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX,methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX,3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX,1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxolan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX,5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimi din-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,(5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, methyl ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX,methyl (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, methyl (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]prop-2-enoate + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo(商標) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX,Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX,Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX,Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX,Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX,Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,
[0066] Combinations of the present ingredient in group (c) above with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, (1H-indol-3-yl)acetic acid (IAA) + SX, 4-(1H-indol-3-yl)butyric acid (IBA) + SX, 2-(4-chloro-2-methylphenoxy)acetic acid (MCPA) + SX, 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB) + SX, 4-chlorophenoxyacetic acid (4-CPA) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat chloride + SX, chlorpropham + SX, choline chloride + 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, inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintophen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, Thidiazuron + SX, triapenthenol + SX, tribufos + SX, trinexapac-ethyl + SX,Uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 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 irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX,Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX. ,
[0067] Combinations of the present component of the above group (d) with the compound of the present invention: anthraquinone + SX, deet + SX, icaridin + SX.
[0068] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include a weight ratio (compound of the present invention:present component) 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, and the like.
[0069] The compound of the present invention can control harmful arthropods such as harmful insects and harmful mites, harmful mollusks, and harmful nematodes. Examples of harmful arthropods, harmful mollusks, and harmful nematodes include the following.
[0070] Hemiptera: Small brown planthopper (Laodelphax striatellus), Brown planthopper (Nilaparvata lugens), White-backed planthopper (Sogatella furcifera), Corn planthopper (Peregrinus maidis), Yellow leafhopper (Javesella pellucida), Black horned planthopper (Perkinsiella saccharicida), Tagosodes orizicolus, Stenocranus pacificus and other Delphacidae; Green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), Black-striped green rice leafhopper (Nephotettix nigropictus), Lightning leafhopper (Recilia dorsalis), Tea green leafhopper (Empoasca Cicadellidae, such as the potato leafhopper (Empoasca fabae), the corn leafhopper (Dalbulus maidis), the white giant leafhopper (Cofana spectra), and Amrasca biguttula biguttula; Aphrophoridae, such as the European spittlebug (Philaenus spumarius); Cercopidae, such as Mahanarva posticata and Mahanarva fimbriolata;Black bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), willow aphid (Aphis spiraecola), green peach aphid (Myzus persicae), strawberry aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), false radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat collar aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus black aphid (Toxoptera citricida), peach butterbur aphid (Hyalopterus pruni), barnyard millet aphid (Melanaphis sacchari), Japanese black aphid (Tetraneura nigriabdominalis), cotton aphid (Ceratovacuna lanigera), apple aphid (Eriosoma lanigerum), English grain aphid (Sitobion avenae), etc. Aphididae; grape aphid (Daktulosphaira vitifoliae), pecan phylloxera (Phylloxera devastatrix), pecan leaf phylloxera (Phylloxera notabilis), southern pecan leaf phylloxera (Phylloxera Phylloxeridae, such as (Russelae);Adelgidae, such as the Japanese hemlock aphid (Adelges tsugae), the balsam woolly aphid (Adelges piceae), and the small brown aphid (Aphrastasia pectinatae); Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, and Nezara Pentatomidae, such as the brown stink bug (Euschistus heros), the red-banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus, and the spotted stink bug (Piezodorus hybneri); Cydnidae, such as the narrow-banded stink bug (Riptortus clavatus), the spider stink bug (Leptocorisa chinensis), and the narrow-banded stink bug (Leptocorisa acuta); Cletus punctiger, Leptoglossus Coreidae, such as Cavelerius saccharivorus, Togo hemipterus, and Blissus leucopterus; Lygaeidae, such as Cavelerius saccharivorus, Togo hemipterus, and Blissus leucopterus;Miridae (Miridae) such as the red-bearded green rice bug (Trigonotylus caelestialium), the red-striped rice bug (Stenotus rubrovittatus), the long-spined wheat rice bug (Stenodema calcarata), and the rusty rice bug (Lygus lineolaris); Aleyrodidae (Aleyrodidae) such as the greenhouse whitefly (Trialeurodes vaporariorum), the tobacco whitefly (Bemisia tabaci), the citrus whitefly (Dialeurodes citri), the citrus spine whitefly (Aleurocanthus spiniferus), the tea spine whitefly (Aleurocanthus camelliae), and the Japanese oak leaf butterflies (Pealius euryae); cyanophylli), red scale (Aonidiella aurantii), pear scale (Diaspidiotus perniciosus), mulberry scale (Pseudaulacaspis pentagona), Yanon scale (Unaspis yanonensis), false Yanon scale (Unaspis citri) and other scale insects (Diaspididae); Coccidae such as ruby scale (Ceroplastes rubens); Margarodidae such as Icerya purchasi and yellow cotton scale (Icerya seychellarum);Pseudococcidae, such as the eggplant mealybug (Phenacoccus solani), the sable mealybug (Phenacoccus solenopsis), the wisteria mealybug (Planococcus kraunhiae), the mulberry mealybug (Pseudococcus comstocki), the citrus mealybug (Planococcus citri), the moth mealybug (Pseudococcus calceolariae), the long-legged mealybug (Pseudococcus longispinus), and the tuttlemey bug (Brevennia rehi); the citrus psyllid (Diaphorina citri), the citrus psyllid (Trioza erytreae), the pear psyllid (Cacopsylla pyrisuga), and the Chinese pear psyllid (Cacopsylla Psyllidae, such as the Japanese chinensis, the potato psyllid (Bactericera cockerelli), and the cacopsylla (Cacopsylla pyricola); Tingidae, such as the plane tree earworm (Corythucha ciliata), the goldenrod earworm (Corythucha marmorata), the Japanese pear earworm (Stephanitis nashi), and the azalea earworm (Stephanitis pyrioides); Cimicidae, such as the bedbug (Cimex lectularius) and the netted whitefly (Cimex hemipterus); Cicadidae, such as the Quesada gigas; Triatoma infestans, Triatoma rubrofasciata, and Triatoma Reduviidae, such as the Venezuelan assassin bug (Rhodonius prolixus);
[0071] Lepidoptera: Chilo suppressalis, Dark-headed stem borer, Chilo polychrysus, White stem borer, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Rice leaf borer, Cnaphalocrocis medinalis, Marasmia patnalis, Rice casino borer, Marasmia exigua, Cotton borer, Notarcha derogata, European corn borer, Ostrinia furnacalis, European corn borer, Hellula undalis, Black-spotted corn borer, Herpetogramma luctuosale, Rice stalk moth, Nymphula Crambidae, such as the Japanese corn moth (Elasmopalpus lignosellus), the Indian meal moth (Plodia interpunctella), the Japanese two-spotted moth (Euzophera batangensis), and the Japanese striped moth (Cadra cautella);Common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), armyworm (Mythimna separata), armyworm (Mamestra brassicae), rice armyworm (Sesamia inferens), white armyworm (Spodoptera mauritia), two-banded cutworm (Naranga aenescens), leaf fall armyworm (Spodoptera frugiperda), African armyworm (Spodoptera exempta), Spodoptera cosmioides, semi-tropical armyworm (Spodoptera eridania), red cutworm (Agrotis ipsilon), turnip cutworm (Agrotis segetum), red rice looper (Autographa nigrisigna), rice yellow looper (Plusia festucae), soybean Heliothis spp. such as the cotton bollworm (Chrysodeixis includens), Trichoplusia spp., and Heliothis spp. such as the false tobacco budworm (Heliothis virescens), Helicoverpa spp. such as the cotton bollworm (Helicoverpa armigera) and the corn earworm (Helicoverpa zea), Noctuidae such as the velvet bean caterpillar (Anticarsia gemmatalis), the cotton leafworm (Alabama argillacea), and the hop wine borer (Hydraecia immanis); Pieridae such as the cabbage white butterfly (Pieris rapae);Pear fruit moth (Grapholita molesta), plum fruit moth (Grapholita dimorpha), bean fruit moth (Leguminivora glycinivorella), adzuki bean pea moth (Matsumuraeses azukivora), apple smaller tortrix (Adoxophyes orana fasciata), tea smaller tortrix (Adoxophyes honmai), tea tortrix (Homona magnanima), green tea tortrix (Archips fuscocupreanus), codling moth (Cydia pomonella), citrus fruit borer (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), citrus fruit borer (Citripestis sagittiferella), European grape wine moth (Lobesia Tortricidae such as Caloptilia theivora and Phyllonorycter ringoniella; Gracilariae such as Carposinidae; Leucoptera coffeella, Lyonetiidae such as Lyonetia clerkella, Lyonetia prunifoliella; Lymantria spp. such as Lymantria dispar, Euproctis spp. such as Euproctis pseudoconspersa; Plutella xylostella Plutellidae, such as Plutellidae (Plutella xylostella);Gelechiidae (Gelechiidae) such as the peach leaf moth (Anarsia lineatella), the potato leaf moth (Helcystogramma triannulella), the red bollworm moth (Pectinophora gossypiella), the potato tuber moth (Pthorimaea operculella), and the tomato leaf moth (Tuta absoluta); Arctiidae (Arctiidae) such as the American fall webworm (Hyphantria cunea); Castniidae (Castniidae) such as the giant sugarcane borer (Telchin licus); Cossidae (Cossidae) such as the small box moth (Cossus insularis); Geometridae (Geometridae) such as the mugwort geometrid (Ascotis selenaria); Parasa Limacodidae such as Stathmopodidae (Stathmopoda masinissa) and the like; Sphingidae such as Acherontia lachesis (Sphingidae); Sesiidae such as Nokona feralis (Nokona feralis), Synanthedon hector (Synanthedon tenuis) and the like; Hesperiidae such as Parnara guttata (Parnara guttata); Tineidae such as Tinea translucens (Tineola bisselliella) and the like.
[0072] Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, and Scirtothrips perseae; Phlaeothripidae such as Haplothrips aculeatus.
[0073] Diptera: Anthomyiidae such as Delia platura, Delia antiqua, and Pegomya cunicularia; Ulidiidae such as Tetanops myopaeformis; Agromyzidae such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola; Chloropidae such as Chlorops oryzae; Bactrocera Tephritidae, such as the Oriental fruit fly (Bactrocera dorsalis), the eggplant fly (Bactrocera latifrons), the olive fruit fly (Bactrocera oleae), the Queensland fruit fly (Bactrocera tryoni), the Mediterranean fruit fly (Ceratitis capitata), the apple maggot (Rhagoletis pomonella), and the cherry fruit fly (Rhacochlaena japonica); Ephydridae, such as the rice leafminer (Hydrellia griseola), the Asian rice leafminer (Hydrellia philippina), and the rice leafminer (Hydrellia sasakii); Drosophila suzukii Drosophilidae, such as Drosophila melanogaster (Drosophila suzukii) and Drosophila melanogaster; Phoridae, such as Megaselia spiracularis; Psychodidae, such as Clogmia albipunctata;Sciaridae (Sciaridae) such as Bradysia difformis and Bradysia odoriphaga; Cecidomyiidae (Cecidomyiidae) such as Mayetiola destructor and Orseolia oryzae; Diopsidae (Diopsis macrophthalma); Glossinidae (Tsetse flies) such as Glossina palpalis and Glossina morsitans; Simuliidae (Simuliidae) such as Simulium japonicum and Simulium damnosum; Phlebotominae (Phlebotominae); Tipula aino (Craned fly), Tipula oleracea (Common crane fly), and Tipula Tipulidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles mosquito family (Culicidae) such as arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus;Simulidae (Family Simuliidae) such as Prosimulium yezoensis and Simulium ornatum; Tabanidae (Family Tabanus trigonus) and other such flies; Muscidae (Family Musca domestica), Muscina stabulans, Stomoxys calcitrans, Haematobia irritans and other such flies; Calliphoridae (Family Sarcophagidae); Chironomidae (Family Chironomidae) such as Chironomus plumosus, Chironomus yoshimatsui, Glyptotendipes tokunagai and other such flies; Fannidae (Family Fannidae);
[0074] Coleoptera: Diabrotica spp. (e.g., Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cucumber beetle (Diabrotica balteata), Cucumber beetle (Diabrotica speciosa), etc.), Bean leaf beetle (Cerotoma trifurcata), Red-necked leaf beetle (Oulema melanopus), Cucumber leaf beetle (Aulacophora femoralis), Striped flea beetle (Phyllotreta striolata), Cabbage leaf beetle (Phyllotreta cruciferae), Western black leaf beetle (Phyllotreta pusilla, cabbage stem beetle (Psylliodes chrysocephala), hop beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn beetle (Chaetocnema pulicaria), sweet potato leaf beetle (Chaetocnema confinis), potato beetle (Epitrix cucumeris), rice spur beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), four-spotted tortoise beetle (Laccoptera quadrimaculata), tobacco flea beetle (Epitrix hirtipennis), radish leaf beetle (Phaedon Chrysomelidae, such as the two-striped leaf beetle (Medythia nigrobilineata);Carabidae beetles such as the seed corn beetle (Stenolophus lecontei) and the slender seed corn beetle (Clivina impressifrons); Phyllophaga spp. such as the cuprea beetle (Anomala cuprea), the rufocuprea beetle (Anomala rufocuprea), the green beetle (Anomala albopilosa), the Japanese beetle (Popillia japonica), the long-legged beetle (Heptophylla picea), the European chafer (Rhizotrogus majalis), the black marsh beetle (Tomarus gibbosus), the black beetle (Holotrichia spp.), and the June beetle (Phyllophaga crinita); Diloboderus spp. such as Diloboderus abderus. Scarabaeidae (Scarabaeidae) such as Araecerus coffeae (Boll weevil); Anthriibidae (Anthriibidae) such as Cylas formicarius (Sweet potato weevil); Bruchidae (Brachiidae) such as Zabrotes subfasciatus (Brazilian bean weevil); Scolytidae (Scolytidae) such as Tomicus piniperda (Pine bark beetle), Hypothenemus hampei (Coffee berry borer);Potato weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), granaria weevil (Sitophilus granarius), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), white grain weevil (Rhabdoscelus lineaticollis), boll weevil (Anthonomus grandis), grass band weevil (Sphenophorus venatus), southern cornbill bug (Sphenophorus callosus), soybean stalk weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rust gourd weevil (Scepticus The Aracanthus spp. (Aracanthus spp.) such as Aracanthus griseus, Scepticus uniformis, Aracanthus mourei, and the cotton root borer (Eutinobothrus brasiliensis) are also included in the Curculionidae family; the Tenebrionidae (Tenebrionidae) such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus are also included in the Coccinellidae family; the Flat-headed Ladybird (Lyctus brunneus), the Rhizopertha dominica); Ptinidae; Cerambycidae, such as Anoplophora malasiaca, Migdolus fryanus, and Aromia bungii;Elateridae beetles such as the Okinawan wireworm beetle (Melanotus okinawensis), the brown-headed wireworm beetle (Agriotes fuscicollis), the comb beetle (Melanotus legatus), the foot-striped wireworm beetle (Anchastus spp.), the Conoderus spp., the Ctenicera spp., the Limonius spp., and the Aeolus spp.; Staphylinidae beetles such as the blue-leaf rove beetle (Paederus fuscipes); the small-leaved weevils (Anthrenus verbasci) and the white-striped weevils (Dermestes Dermestidae such as Trogoderma granarium (Trogoderma maculates) and the like; Anobiidae such as Lasioderma serricorne (tobacco beetle) and Stegobium paniceum (Anobiidae); Laemophloeidae such as Cryptolestes ferrugineus (Laemophloeidae); Silvanidae such as Oryzaephilus surinamensis (Silvanidae); Nitidulidae such as Brassicogethes aeneus (Blossom beetle).
[0075] Orthoptera: Migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red locust (Nomadacris septemfasciata), Brown locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two-striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clear-winged grasshopper (Camnula pellucida), Desert grasshopper (Schistocerca The grasshoppers (Acrididae) include the common locust (Oxya gregaria), yellow-winged locust (Gastrimargus musicus), sparse-throated locust (Austracris guttulosa), oriental grasshopper (Oxya yezoensis), long-winged locust (Oxya japonica), and Taiwan grasshopper (Patanga succincta); the grasshoppers (Gryllotalpidae) include the common house cricket (Gryllotalpa orientalis); the crickets (Gryllidae) include the European house cricket (Acheta domestica) and the field cricket (Teleogryllus emma); and the katydids (Tettigoniidae) include the Mormon cricket (Anabrus simplex).
[0076] Hymenoptera: Tenthredinidae such as Athalia rosae and Athalia japonica; Solenopsis spp. such as Solenopsis invicta and Solenopsis geminata, Atta spp. such as Atta capiguara, Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomorium pharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole Camponotus spp. such as Camponotus noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, Pogonomyrmex spp. such as Pogonomyrmex occidentalis, Wasmania spp. such as Wasmania auropunctata, Formicidae such as Anoplolepis gracilipes; Vespa mandarinia, Vespa simillima, Vespa analis, Vespa Vespidae, such as Polistes velutina and Polistes jokahamae; Siricidae, such as Urocerus gigas; and Bethylidae.
[0077] Blattodea: Ectobiidae, such as the German cockroach (Blattella germanica); Blattidae, such as the American cockroach (Periplaneta fuliginosa), the American cockroach (Periplaneta americana), the American cockroach (Periplaneta australasiae), the brown cockroach (Periplaneta brunnea), and the Asian cockroach (Blatta orientalis); Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, and Neotermes Termites of the family Termitidae, such as the Satsuma termite (Glyptotermes satsumensis), Nakajima termite (Glyptotermes nakajimai), Katan termite (Glyptotermes fuscus), Hodotermopsis sjostedti, Koshu termite (Coptotermes guangzhouensis), Amami termite (Reticulitermes amamianus), Miyatake termite (Reticulitermes miyatakei), Formosan termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Snocapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.
[0078] Order Siphonaptera: Family Pulicidae such as human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), rat flea (Xenopsylla cheopis), chicken flea (Echidnophaga gallinacea), etc.; Family Hectopsyllidae such as sand flea (Tunga penetrans); Family Ceratophyllidae such as European rat flea (Nosopsyllus fasciatus).
[0079] Psocodae: Pediculidae, such as head louse (Pediculus humanus capitis); Pthiridae, such as pubic louse (Pthirus pubis); Haematopinidae, such as cow louse (Haematopinus eurysternus) and pig louse (Haematopinus suis); Linognathidae, such as cow louse (Linognathus vituli), sheep trunk louse (Linognathus ovillus), and woolly cow louse (Solenopotes capillatus); Bovicola bovis, sheep louse (Bovicola ovis), Bovicola breviceps, Damalinia Bovicoliidae, such as Trichodectes canis and Felicola subrostratus; Menoponidae, such as Menopon gallinae, Menacanthus stramineus, and Trinoton spp.; Trimenoponidae, such as Cummingsia spp.; Trogiidae, such as Trogium pulsatorium; Liposcelis corrodens and Liposcelis Liposcelidae or Liposcelididae, such as Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelis entomophila.
[0080] Thysanura: Family Lepismatidae, including the Japanese silverfish (Ctenolepisma villosa) and the European silverfish (Lepisma saccharina).
[0081] Acari: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp.; Aculops pelekassi, Aculops citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculops spp. Eriophyidae such as Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae such as Polyphagotarsonemus latus; Tenuipalpidae such as Brevipalpus phoenicis; Tuckerellidae;Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Rocky Mountain wood tick (Dermacentor andersoni), Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Black-legged tick (Ixodes scapularis), Western black-legged tick (Ixodes pacificus), Ixodes holocyclus, Ixodes ricinus, Lone star tick (Amblyomma Ixodidae ticks such as Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, and Rhipicephalus decoloratus; Argasidae ticks such as Argas persicus, Ornithodoros hermsi, and Ornithodoros turicata; Acaridae ticks such as Tyrophagus putrescentiae and Tyrophagus similis; Dermatophagoides farinae and Dermatophagoides pteronyssinus. Pyroglyphidae, such as Pteronyssinus;Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, and Cheyletiella yasguri; Psoroptidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, and Chorioptes spp.; Notoedres cati, Notoedres muris, and Sarcoptes Sarcoptidae such as (Scabiei); Listrophoridae such as (Listrophorus gibbus); Dermanyssidae such as (Dermanyssus gallinae); Macronyssidae such as (Ornithonyssus sylviarum) and (Ornithonyssus bacoti); Varroa destructor such as (Varroa jacobsoni); Demodicidae such as (Demodex canis) and (Demodex cati); Leptotrombidium akamushi and (Leptotrombidium Trombiculidae, such as Leptotrombidium scutellare, Leptotrombidium pallidum, and Leptotrombidium scutellare.
[0082] Araneae: Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii. Polydesmida: Paradoxosomatidae, such as Oxidus gracilis and Nedyopus tambanus. Isopoda: Armadillidiidae, such as Armadillidium vulgare. Chilopoda: Scutigeridae such as Thereuonema hilgendorfi; Scolopendridae such as Scolopendra subspinipes; Ethopolyidae such as Bothropolys rugosus. Class Gastropoda: Family Limacidae such as the brown slug (Limax marginatus) and the yellow slug (Limax flavus); Family Philomycidae such as the slug (Meghimatium bilineatum); Family Ampullariidae such as the apple snail (Pomacea canaliculata); Family Lymnaeidae such as the lymnae snail (Austropeplea ollula).
[0083] Nematoda: Aphelenchoididae, such as the rice root-lesion nematode (Aphelenchoides besseyi); Pratylenchidae, such as Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus neglectus, and Radopholus similis; Meloidogyne javanica, Meloidogyne incognita, guava root-knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, soybean cyst nematode (Heterodera glycines), potato cyst nematode (Globodera Heteroderidae such as Globodera rostochiensis, potato white cyst nematode (Globodera pallida), and Colombian root-knot nematode (Meloidogyne chitwoodi); Hoplolaimidae such as Rotylenchulus reniformis; Anguinidae such as Nothotylenchus acris and Ditylenchus dipsaci; Tylenchulidae such as Tylenchulus semipenetrans; Longidoridae such as Xiphinema index; Trichodoridae; Parasitaphelenchidae such as Bursaphelenchus xylophilus.
[0084] The harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes may be harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes that have reduced sensitivity to insecticides, acaricides, molluscicides, or nematocides, or that have developed resistance to the insecticides, acaricides, molluscicides, or nematocides.
[0085] The method for controlling arthropod pests of the present invention is carried out by applying an effective amount of the compound of the present invention or composition A directly to the arthropod pests and / or to the habitat of the arthropod pests (plants, soil, houses, animals, etc.). Examples of the method for controlling arthropod pests of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, and seed treatment.
[0086] The compound of the present invention or Composition A is typically mixed with an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier, and a surfactant, and formulation adjuvants such as binders, dispersants, and stabilizers are added as needed to formulate the compound into an aqueous suspension, oil suspension, oil concentrate, emulsifiable concentrate, emulsion, microemulsion, microcapsule, wettable powder, water dispersible granule, dust, granule, tablet, aerosol, resin formulation, or the like. The compound of the present invention or Composition A can be formulated into any dosage form, including but not limited to these, as described in "Manual on development and use of FAO and WHO Specifications for pesticides," FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain 0.0001 to 99% by weight of the compound of the present invention or Composition A.
[0087] Examples of solid carriers include 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, fine powder and granular chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).
[0088] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).
[0089] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.
[0090] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).
[0091] Other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc., and specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acid isopropyl phosphate, and dibutylhydroxytoluene.
[0092] In addition, adjuvants can be used as components that enhance or support the efficacy of the compound of the present invention. Specific examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).
[0093] In the present invention, the plant includes the whole plant, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.
[0094] Vegetative reproductive organs refer to plant roots, stems, leaves, and other parts that can grow when separated from the main body and placed in soil. 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. Stolons are sometimes called runners, and propagules are also called bulbils and are divided into broad buds and bulbils. Vines refer to shoots (a collective term for leaves and stems) of plants such as sweet potatoes and Japanese yams. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores, and tuberous roots are collectively called bulbils. Potato cultivation begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.
[0095] Examples of the method for controlling harmful arthropods by applying an effective amount of the compound of the present invention or composition A to soil include a method of applying an effective amount of the compound of the present invention or composition A to soil before or after planting a plant. More specifically, for example, planting hole treatment (spraying in planting holes, mixing in planting hole treatment soil), plant base treatment (spraying in planting holes, mixing in plant base soil, plant base irrigation, plant base treatment in the latter half of the seedling raising period), planting furrow treatment (spraying in planting furrows, mixing in planting furrow soil), row treatment (row spraying, row soil mixing, row spraying in the growing season), row treatment at sowing (row spraying at sowing, mixing in row soil at sowing), overall treatment (overall soil spraying, overall soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spray treatments (foliar spraying of granules during the growing season, spraying under the crown or around the main trunk, soil surface spraying, soil surface mixing, seeding hole spraying, furrow surface spraying, spraying between plants), and others. Other irrigation treatments include soil irrigation, seedling irrigation, chemical injection treatment, ground level irrigation, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling bed treatments (seedling bed spraying, seedling bed irrigation, water seedling bed spraying, seedling immersion), bed soil mixing treatments (bed soil mixing, bed soil mixing before sowing, spraying before soil covering at sowing, spraying after soil covering at sowing, covering soil mixing), and other treatments (hilling soil mixing, plowing in, topsoil mixing, rain-drop soil mixing, planting position treatment, granular inflorescence spraying, paste fertilizer mixing).
[0096] Seed treatments include, for example, treatment of seeds or vegetative reproductive organs with the compound of the present invention or Composition A. More specifically, examples include spray treatments in which a suspension of the compound of the present invention or Composition A is sprayed onto the surface of seeds or vegetative reproductive organs in a mist; smear treatments in which the compound of the present invention or Composition A is applied to seeds or vegetative reproductive organs; immersion treatments in which seeds or vegetative reproductive organs are immersed in a solution of the compound of the present invention or Composition A for a certain period of time; and methods of coating seeds or vegetative reproductive organs with a carrier containing the compound of the present invention or Composition A (film coating treatment, pellet coating treatment, etc.). Seed potatoes are particularly examples of the vegetative reproductive organs mentioned above. When applying Composition A to seeds or vegetative reproductive organs, Composition A can be applied to the seeds or vegetative reproductive organs as a single formulation, or different formulations of Composition A can be applied to the seeds or vegetative reproductive organs in multiple separate applications. Examples of methods for treating seeds or vegetative reproductive organs with multiple different formulations of Composition A include a method of treating seeds or vegetative reproductive organs with a formulation containing only the compound of the present invention as an active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing this ingredient; and a method of treating seeds or vegetative reproductive organs with a formulation containing both the compound of the present invention and this ingredient as active ingredients, air-drying the seeds or vegetative reproductive organs, and then treating with a formulation containing a component other than the component already treated. In the present invention, "seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A" refers to seeds or vegetative reproductive organs to which the compound of the present invention or Composition A is attached. The seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A may have materials other than the compound of the present invention or Composition A attached to them before or after the compound of the present invention or Composition A is attached to the seeds or vegetative reproductive organs. Furthermore, when Composition A is attached to the surface of the seeds or vegetative reproductive organs in layers, the layers may consist of one layer or multiple layers. Furthermore, when the layer 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 containing no active ingredients. Seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A can be obtained, for example, by applying a formulation containing the compound of the present invention or Composition A to seeds or vegetative reproductive organs by the seed treatment method described above.
[0097] When the compound of the present invention or composition A is used for controlling harmful arthropods in the agricultural field, the application amount is 10,000 m 2 The amount of the compound of the present invention is usually 1 to 10,000 g per kg of seed or vegetative reproductive organ. When treating seeds or vegetative reproductive organs, the compound of the present invention is usually applied in an amount within the range of 0.001 to 100 g per kg of seed or vegetative reproductive organ. When the compound of the present invention or Composition A is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate, etc., it is usually applied after being diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm, and granules, dusts, etc. are usually applied as is.
[0098] The compound of the present invention or composition A can also be applied by wrapping a resin preparation in the form of a sheet or string around the crop, stretching it near the crop, or spreading it on the soil around the base of the plant.
[0099] When the compound of the present invention or composition A is used to control harmful arthropods living in houses, the application amount is 1 / 2 m / day for surface treatment. 2 The amount of the compound of the present invention per square meter is usually 0.01 to 1,000 mg. 3 When the compound of the present invention or Composition A is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate or the like, it is usually applied after diluting with water so that the active ingredient concentration becomes 0.1 to 10,000 ppm, whereas oil solutions, aerosols, fumigants, poison baits and the like are applied as they are.
[0100] When the compound of the present invention or Composition A is used to control ectoparasites in livestock such as cattle, horses, pigs, sheep, goats, and chickens, or small animals such as dogs, cats, rats, and mice, it can be administered to animals by methods known in veterinary medicine. Specific methods of administration include, for example, administration by tablet, incorporation into feed, suppository, or injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) for systemic control, and administration by methods such as spraying an oil or aqueous liquid, pour-on application, spot-on application, washing the animal with a shampoo formulation, or attaching a resin formulation to the animal as a collar or ear tag. When administered to animals, the amount of the compound of the present invention or Composition A is usually in the range of 0.1 to 1000 mg per kg of the animal's body weight.
[0101] The compound of the present invention or Composition A can be used as an agent for controlling harmful arthropods in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.
[0102] Corn (horse-tooth, hard grain, soft grain, explosive, glutinous, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, waxy barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland type, pima type), soybean (fully harvested seed varieties, edamame varieties, green-harvested varieties, indeterminate, determinate, semi-determinate types), peanuts, buckwheat, sugar beet (sugar production, animal feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (oil production, food, ornamental), sugarcane, tobacco, tea plant, mulberry, solanaceous vegetables (eggplant, tomato, bell pepper, chili pepper) , potatoes, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Umbelliferae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, scallions, Sweet potatoes, pome fruits (apples, European pears, Japanese pears, Chinese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants,Turfgrass, pasture grass,
[0103] The above-mentioned plants are not particularly limited as long as they are varieties that are commonly cultivated, and include plants that can be produced by natural crossbreeding, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants that have been conferred resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants that are capable of synthesizing selective toxins known to be found in the genus Bacillus, such as Bacillus thuringiensis; and plants that can be conferred specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insect.
[0104] The present invention will be explained in more detail below with reference to production examples, formulation examples, test examples, etc., but the present invention is not limited to these examples. In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, t-Bu represents a tert-butyl group, C 2 F 5 represents a perfluoroethyl group, c-Pr represents a cyclopropyl group, CF3 represents a trifluoromethyl group, CF2H represents a difluoromethyl group, Ph represents a phenyl group, Py2 represents a 2-pyridyl group, Py3 represents a 3-pyridyl group, and Py4 represents a 4-pyridyl group. When c-Pr, Ph, Py2, Py3, and Py4 have a substituent, the substituent is written before the symbol along with the substitution position. For example, 1-CN-c-Pr represents a 1-cyanocyclopropyl group, and 3,4-F 2 -Ph represents a 3,4-difluorophenyl group, and 2-C 2 F 5-Ph represents a 2-(perfluoroethyl)phenyl group, and 4-SO 2 CF 3 -Ph represents a 4-(trifluoromethanesulfonyl)phenyl group, and 3,4-(OCF 3 ) 2 -Ph represents a 3,4-bis(trifluoromethoxy)phenyl group, and 3-SCF 3 -4-OCF 3 -Ph represents a 3-[(trifluoromethyl)thio]-4-(trifluoromethoxy)phenyl group, and 4-CF 3 -Py2 represents a 4-(trifluoromethyl)-2-pyridyl group, 3-CF2H-1-i-Pr-1H-pyrrol-2-yl represents a 3-difluoromethyl-1-isopropyl-2-1H-pyrrolyl group, 4-CF2H-1-Me-1H-imidazole-2-yl represents a 4-difluoromethyl-1-methyl-2-1H-imidazolyl group, and 3-CF2H-1-Me-1H-pyrazol-5-yl represents a 3-difluoromethyl-1-methyl-5-1H-pyrazolyl group.
[0105] First, examples of the preparation of the compounds of the present invention and their intermediates will be shown.
[0106] When the physical properties of a compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] + or [M-H] - and retention time (hereinafter referred to as RT). The conditions for liquid chromatography (hereinafter referred to as LC) are as follows:
[0107] [LC conditions] Column: L-column 2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemicals Evaluation and Research Institute, Japan) UV measurement wavelength: 254 nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Gradient conditions: Solution was delivered at the concentration gradient shown in [Table LC1].
[0108]
[0109] Reference Production Example 1 To a mixture of 0.7 g of 5-methylisoxazole-5-carboxylic acid and 10 mL of pyridine were added 1.6 g of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1.5 g of 6-iodo-3-(ethylthio)imidazo[1,2-a]pyridin-2-amine (hereinafter referred to as Intermediate Z) produced by the method described in WO 2018 / 052136, and the mixture was stirred for 4 hours at 80° C. Water was added to the resulting mixture, and the precipitated solid was filtered off and dried to obtain 1.8 g of Intermediate 1 represented by the following formula: Intermediate 1: 1 H-NMR (CDCl3): 8.73 (1H, br s), 8.64-8.63 (1H, m), 7.54-7.51 (1H, m), 7.49-7.47 (1H, m), 7.32 (1H, s), 6.86 (1H, t), 2.75 (2H, q), 1.25 (3H, t).
[0110] Reference Production Example 1-1 The compound produced in accordance with Reference Production Example 1 and its physical properties are shown below. Formula (A-1) In the compound represented by the formula: 1 , X 1 , X 2 , X 3 , G 2 , and G 3 A compound in which the combination is any of the combinations described in [Table A-1].
[0111] Intermediate 2: 1 H-NMR (CDCl 3 ) δ: 8.62-8.61 (1H, m), 8.19 (1H, br s), 7.54 (1H, d), 7.53-7.46 (2H, m), 6.73 (1H, d), 4.27 (3H, s), 2.72 (2H, q), 1.24 (3H, t). Intermediate 3: 1 H-NMR (CDCl 3) δ: 8.62-8.61 (1H, m), 8.25 (1H, brs), 7.51-7.49 (2H, m), 6.97 (1H, s), 4.31 (3H, s), 2.73 (2H, q), 1.25-1.23 (3H, m). Intermediate 4: LCMS: 464 [M+H] +, RT = 1.79 min Intermediate 5: 1 H-NMR (CDCl 3 ) δ: 8.64-8.63 (1H, m), 8.56 (1H, br s), 7.52-7.49 (1H, m), 7.46-7.44 (1H, m), 7.36-7.35 (1H, m), 6.98-6.97 (1H, m), 2.76 (2H, q), 1.25 (3H, t). Intermediate 6: LCMS: 498 [M+H] +, RT = 2.06 min Intermediate 7: 1 H-NMR (CDCl 3 ) δ: 8.64-8.64 (1H, m), 8.41-8.41 (1H, m), 8.31 (1H, br s), 7.54-7.52 (1H, m), 7.45-7.43 (1H, m), 2.76 (2H, q), 1.24 (3H, t). Intermediate 8: 1 H-NMR (CDCl 3 ) δ: 8.54-8.54 (2H, m), 8.44-8.44 (1H, m), 7.54 (1H, dd), 7.41 (1H, dd), 2.77 (2H, q), 1.24 (3H, t). Intermediate 9: 1 H-NMR (CDCl 3 ) δ: 8.77-8.76 (1H, m), 8.47 (1H, br s), 8.45-8.44 (1H, m), 7.76 (1H, d), 7.50 (1H, dd), 2.80 (2H, q), 1.26 (3H, t). Intermediate 10: LCMS: 499 [M+H] +, RT = 1.91 min Intermediate 11: LCMS: 451 [M+H] +, RT = 1.86 min Intermediate 12: LCMS: 465 [M+H] +, RT = 1.83 min Intermediate 13: 1 H-NMR (CDCl 3) δ: 9.53 (1H, br s), 8.64-8.64 (1H, m), 8.07-8.07 (1H, m), 7.53-7.50 (1H, m), 7.49-7.46 (1H, m), 2.75 (2H, q), 1.25 (3H, t).
[0112] Reference Production Example 1-2 The compound produced in accordance with Reference Production Example 1 and its physical properties are shown below. Formula (A-2) In the compound represented by the formula: 2 , X 1 , X 2 , X 4 , G 2 , and G 3 A compound in which the combination is any of the combinations described in [Table A-2]. Intermediate 14: 1 H-NMR (CDCl 3 ) δ: 8.60-8.60 (1H, m), 8.29 (1H, br s), 8.12 (1H, s), 7.47-7.46 (2H, m), 4.01 (3H, s), 2.70 (2H, q), 1.20 (3H, t). Intermediate 15: 1 H-NMR (CDCl 3 ) δ: 8.59 (1H, br s), 8.51-8.50 (1H, m), 8.10 (1H, s), 7.56 (1H, d), 7.35 (1H, dd), 6.93 (1H, t), 3.98 (3H, s), 2.70 (2H, q), 1.21 (3H, t). Intermediate 16: LCMS: 496[M+H]+, RT =1.95 min Intermediate 17: 1 H-NMR (CDCl 3) δ: 9.13 (1H, br s), 8.61-8.60 (1H, m), 7.46-7.45 (2H, m), 6.99 (1H, s), 3.97 (3H, s), 2.71 (2H, q), 1.22 (3H, t). Intermediate 18: LCMS: 494 [M+H] +, RT = 1.85 min Intermediate 19: LCMS: 464 [M+H] +, RT = 1.69 min Intermediate 20: LCMS: 454 [M+H] +, RT = 1.70 min Intermediate 21: LCMS: 496 [M+H] +, RT = 1.83 min Intermediate 22: LCMS: 478 [M+H] +, RT = 1.86 min Intermediate 23: 1 H-NMR (CDCl 3 ) δ: 8.63-8.63 (1H, m), 8.47 (1H, s), 8.19 (1H, br s), 8.15 (1H, s), 7.52-7.49 (1H, m), 7.42 (1H, d), 2.74 (2H, q), 1.23 (3H, t). Intermediate 24: LCMS: 464[M+H]+, RT =1.63 min Intermediate 25: LCMS: 454[M+H]+, RT =1.55 min Intermediate 26: LCMS: 496[M+H]+, RT =1.75 min Intermediate 27: LCMS: 497[M+H]+, RT =1.79 min Intermediate 28: LCMS: 495[M+H]+, RT =1.69 minutes Intermediate 29: LCMS: 483 [M+H] +, RT =2.02 minutes Intermediate 30: LCMS: 457 [M+H] +, RT =1.96 minutes Intermediate 31: LCMS: 409 [M+H] +, RT =1.93 minutes Intermediate 32: LCMS: 399 [M+H] +, RT =1.98 minutes Intermediate 33: LCMS: 457 [M+H] +, RT =1.94 minutes Intermediate 34: LCMS: 409 [M+H] +, RT =1.90 minutes
[0113] Preparation Example 1: To a mixture of 1.2 g of Intermediate 1, 2.4 g of cesium carbonate, and 5 mL of DMF, 0.31 mL of methyl iodide was added under ice cooling, and the mixture was stirred at room temperature for 5 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. The resulting residue was subjected to silica gel chromatography to obtain 1.1 g of Compound 1 of the present invention. Compound 1 of the present invention: 1 H-NMR (CDCl3) δ: 8.60-8.59 (1H, m), 7.56-7.53 (1H, m), 7.39-7.36 (1H, m), 6.75-6.56 (1H, m), 6.65 (1H, t), 3.56 (3H, s), 2.59 (2H, q), 1.17 (3H, t).
[0114] Preparation Example 1-1 The compound prepared in accordance with Preparation Example 1 and its physical properties are shown below. Formula (B-1) In the compound represented by the formula 1 , X 1 , X 2 , X 3 , G 2 , G 3 and R 1 The combination of is any of the combinations described in [Table B-1]
[0115] Compound 2 of the present invention: 1 H-NMR (CDCl3) δ: 8.46 (1H, s), 7.53 (1H, d), 7.41 (1H, d), 7.08 (1H, s), 5.63 (1H, s), 4.16 (3H, s), 3.51 (3H, s), 2.37 (2H, q), 1.13 (3H, t). Compound 3 of the present invention: 1 H-NMR (CDCl3) δ: 8.49-8.48 (1H, m), 7.57-7.55 (1H, m), 7.43-7.40 (1H, m), 5.93 (1H, s), 4.19 (3H, s), 3.52 (3H, s), 2.46 (2H, q), 1.14 (3H, t). Compound 4 of the present invention: 1H-NMR (CDCl3) δ: 8.48-8.48 (1H, m), 7.92 (1H, t), 7.56 (1H, dd), 7.43 (1H, dd), 7.37 (1H, s), 5.74 (1H, s), 3.51 (3H, s), 2.40 (2H, q), 1.12 (3H, t). Compound 5 of the present invention: 1 H-NMR (CDCl3) δ: 8.60-8.60 (1H, m), 7.54-7.52 (1H, m), 7.38-7.36 (1H, m), 6.66-6.62 (1H, m), 6.66-6.66 (1H, m), 3.53 (3H, s), 2.54 (2H, q), 1.15 (3H, t). Compound 6 of the present invention: 1 H-NMR (CDCl3) δ: 8.56-8.55 (1H, m), 7.59-7.56 (1H, m), 7.46-7.43 (1H, m), 7.08-7.06 (1H, m), 6.79-6.77 (1H, m), 3.50 (3H, s), 2.46 (2H, q), 1.12 (3H, t). Compound 7 of the present invention: 1 H-NMR (CDCl3) δ: 8.57-8.56(1H, m), 7.61-7.58(1H, m),7.50-7.50(1H, m),7.46-7.43(1H, m),3.53(3H, s),2.55(2H, q), 1.15(3H, t). Compound 8 of the present invention: 1 H-NMR (CDCl3) δ: 8.47-8.46 (1H, m), 7.56 (1H, dd), 7.51 (1H, d), 7.49 (1H, dd), 3.53 (3H, s), 2.55 (2H, q), 1.15 (3H, t). Compound 9 of the present invention: 1 H-NMR (CDCl3) δ: 8.69-8.68 (1H, m), 7.77 (1H, d), 7.57 (1H, dd), 7.49-7.49 (1H, m), 3.55 (3H, s), 2.58 (2H, q), 1.16 (3H, t). Compound 10 of the present invention: LCMS: 513[M+H]+, RT =2.02 minutes Compound 11 of the present invention: 1H-NMR (CDCl3) δ: 8.21 (1H, dd), 7.85 (1H, dd), 7.54-7.53 (1H, m), 7.15 (1H, dd), 3.52 (3H, s), 2.53 (2H, q), 1.13 (3H, t). Compound 12 of the present invention: 1 H-NMR (CDCl3) δ: 8.59-8.59 (1H, m), 7.61-7.58 (1H, m), 7.46-7.43 (1H, m), 7.35 (1H, s), 3.48 (3H, s), 2.57 (2H, q), 1.16 (3H, t). Compound 13 of the present invention: 1 H-NMR (CDCl3) δ: 8.63-8.62 (1H, m), 7.78 (1H, s), 7.51-7.48 (1H, m), 7.33-7.31 (1H, m), 3.62 (3H, s), 2.63 (2H, q), 1.17 (3H, t).
[0116] Preparation Example 1-2 The compound prepared in accordance with Preparation Example 1 and its physical properties are shown below. Formula (B-2) In the compound represented by the formula 2 , X 1 , X 2 , X 4 , G 2 , G 3 and R 1 The combination of is any of the combinations described in [Table B-2]
[0117] Compound 14 of the present invention: 1 H-NMR (CDCl3) δ: 8.53-8.52 (1H, m), 7.55-7.53 (1H, m), 7.42-7.39 (1H, m), 7.05 (1H, s), 3.71 (3H, s), 3.46 (3H, s), 2.52 (2H, q), 1.13 (3H, t). Compound 15 of the present invention: 1H-NMR (CDCl3) δ: 8.45-8.45 (1H, m), 7.55 (1H, d), 7.45 (1H, dd), 7.21 (1H, t), 6.77 (1H, s), 3.69 (3H, s), 3.45 (3H, s), 2.48 (2H, q), 1.11 (3H, t). Compound 16 of the present invention: 1 H-NMR (CDCl3) δ: 8.57-8.57 (1H, m), 7.52-7.49 (1H, m), 7.41-7.38 (1H, m), 6.74 (1H, s), 3.74 (3H, s), 3.54 (3H, s), 2.53 (2H, q), 1.13 (3H, t). Compound 17 of the present invention: 1 H-NMR (CDCl3) δ: 8.57-8.57 (1H, m), 7.50 (1H, dd), 7.40 (1H, d), 6.26 (1H, s), 3.67 (3H, s), 3.52 (3H, s), 2.52 (2H, q), 1.12 (3H, t). Compound 18 of the present invention: 1 H-NMR (CDCl3) δ: 8.57-8.56 (1H, m), 7.49 (1H, dd), 7.39 (1H, dd), 6.37 (1H, t), 5.93 (1H, s), 3.52 (3H, s), 3.51 (3H, s), 2.52 (2H, q), 1.12 (3H, t). Compound 19 of the present invention: 1 H-NMR (CDCl3) δ: 8.54-8.54 (1H, m), 7.58 (1H, d), 7.52-7.50 (1H, m), 7.40-7.38 (1H, m), 6.92 (1H, t), 6.43 (1H, s), 3.55 (3H, s), 2.47 (2H, q), 1.11 (3H, t). Compound 20 of the present invention: LCMS: 468 [M+H] +, RT = 1.67 min. Compound 21 of the present invention: 1H-NMR (CDCl3) δ: 8.53-8.52 (1H, m), 7.49 (1H, dd), 7.37 (1H, dd), 7.27 (1H, s), 6.49-6.49 (1H, m), 4.44 (2H, q), 3.54 (3H, s), 2.45 (2H, q), 1.11 (3H, t). Compound 22 of the present invention: LCMS: 492 [M+H] +, RT = 1.77 min. Compound 23 of the present invention: 1 H-NMR (CDCl3) δ: 8.56-8.55 (1H, m), 8.01 (1H, s), 7.59-7.56 (1H, m), 7.45-7.42 (1H, m), 7.00 (1H, s), 3.48 (3H, s), 2.51 (2H, q), 1.12 (3H, t). Compound 24 of the present invention: 1 H-NMR (CDCl3) δ: 8.55-8.55 (1H, m), 7.93 (1H, s), 7.58-7.55 (1H, m), 7.45-7.43 (1H, m), 7.02 (1H, t), 6.99 (1H, s), 3.48 (3H, s), 2.47 (2H, q), 1.10 (3H, t). Compound 25 of the present invention: LCMS: 468 [M+H] +, RT = 1.69 min. Compound 26 of the present invention: 1 H-NMR (CDCl3) δ: 8.47-8.47 (1H, m), 7.50 (1H, dd), 7.37 (1H, dd), 7.03 (1H, s), 3.89 (3H, s), 3.50 (3H, s), 2.56 (2H, q), 1.15 (3H, t). Compound 27 of the present invention: 1 H-NMR (CDCl3) δ: 8.58-8.58 (1H, m), 8.10 (1H, s), 7.50-7.47 (1H, m), 7.37-7.34 (1H, m), 4.88 (2H, q), 3.58 (3H, s), 2.56 (2H, q), 1.15 (3H, t). Compound 28 of the present invention: 1H-NMR (CDCl3) δ: 8.53-8.52 (1H, m), 7.51 (1H, dd), 7.40 (1H, dd), 6.79-6.79 (1H, m), 6.25 (1H, d), 3.44 (3H, s), 3.39 (3H, s), 2.45 (2H, q), 1.10 (3H, t). Compound 29 of the present invention: 1 H-NMR (CDCl3) δ: 8.59-8.59 (1H, m), 7.53-7.51 (1H, m), 7.36-7.34 (1H, m), 7.04 (1H, s), 3.58 (3H, s), 2.66 (2H, q), 1.22-1.17 (3H, m). Compound 30 of the present invention: 1 H-NMR (CDCl3) δ: 8.58-8.57 (1H, m), 7.48 (1H, dd), 7.36 (1H, dd), 6.29 (1H, s), 3.55 (3H, s), 3.01-2.94 (1H, m), 2.60 (2H, q), 1.28-1.20 (6H, m), 1.17 (3H, t). Compound 31 of the present invention: 1 H-NMR (CDCl3) δ: 8.48-8.47 (1H, m), 7.47 (1H, dd), 7.37 (1H, dd), 6.29 (1H, s), 3.55 (3H, s), 3.01-2.94 (1H, m), 2.60 (2H, q), 1.26-1.22 (6H, m), 1.17 (3H, t). Compound 32 of the present invention: LCMS: 413 [M+H]+, RT = 1.96 min. Compound 33 of the present invention: 1 H-NMR (CDCl3) δ: 8.09 (1H, d), 7.97-7.97 (1H, m), 7.19 (1H, dd), 6.28 (1H, s), 3.54 (3H, s), 3.01-2.92 (1H, m), 2.60-2.54 (2H, m), 1.24-1.18 (6H, m), 1.15 (3H, t). Compound 34 of the present invention: LCMS: 423 [M+H]+, RT = 1.90 min
[0118] Preparation Example 2: To a mixture of 0.87 g of compound 1 of the present invention and 10 mL of chloroform, 1.5 g of mCPBA (purity 65%, containing 35% water) was added under ice-cooling and 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 the mixture was stirred at room temperature for 3 hours, followed by extraction with chloroform. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 0.76 g of compound 35 of the present invention. Compound 35 of the present invention: LCMS: 511[M+H]+, RT =1.73 min
[0119] Preparation Example 2-1 The compound prepared in accordance with Preparation Example 2 and its physical properties are shown below. Formula (B-3) In the compound represented by the formula 1 , X 1 , X 2 , X 3 , G 2 , G 3 and R 1 The combination of is any of the combinations described in [Table B-3]
[0120] Inventive compound 36: LCMS: 542[M+H]+, RT =1.87 min Inventive compound 37: LCMS: 494[M+H]+, RT =1.44 min Inventive compound 38: LCMS: 510[M+H]+, RT =1.61 min Inventive compound 39: LCMS: 528[M+H]+, RT =1.83 min Inventive compound 40: LCMS: 545[M+H]+, RT =1.80 min Inventive compound 41: LCMS: 481[M+H]+, RT =1.71 min Inventive compound 42: LCMS: 497[M+H]+, RT =1.77 min Inventive compound 43: LCMS: 471[M+H]+, RT =1.81 min Compound 44 of the present invention: LCMS: 487[M+H]+, RT =1.85 min Inventive compound 45: LCMS: 529[M+H]+, RT =1.76 min Inventive compound 46: LCMS: 545[M+H]+, RT =1.82 min Inventive compound 47: LCMS: 481[M+H]+, RT =1.73 min Inventive compound 48: LCMS: 497[M+H]+, RT =1.79 min Inventive compound 49: LCMS: 511[M+H]+, RT =1.73 min Inventive compound 50: LCMS: 545[M+H]+, RT =1.79 min
[0121] Preparation Example 2-2 The compound prepared in accordance with Preparation Example 2 and its physical properties are shown below. Formula (B-4) In the compound represented by the formula 2 , X 1 , X 2 , X 4 , G 2 , G 3 and R 1 The combination of is any of the combinations described in [Table B-4]
[0122] Compound 51 of the present invention: LCMS: 542[M+H]+, RT =1.69 minutes Compound 52 of the present invention: LCMS: 542[M+H]+, RT =1.80 minutes Compound 53 of the present invention: LCMS: 552[M+H]+, RT =1.66 minutes Compound 54 of the present invention: LCMS: 524[M+H]+, RT =1.43 minutes Compound 55 of the present invention: LCMS: 540[M+H]+, RT =1.60 minutes Compound 56 of the present invention: LCMS: 510[M+H]+, RT =1.63 minutes Compound 57 of the present invention: LCMS: 500[M+H]+, RT =1.60 minutes Compound 58 of the present invention: LCMS: 526[M+H]+, RT =1.41 minutes Compound 59 of the present invention: LCMS: 542[M+H]+, RT =1.57 minutes Compound 60 of the present invention: LCMS: 512[M+H]+, RT =1.49 minutes Compound 61 of the present invention: LCMS: 528[M+H]+, RT =1.71 minutes Compound 62 of the present invention: LCMS: 494[M+H]+, RT =1.40 minutes Compound 63 of the present invention: LCMS: 510[M+H]+, RT =1.57 minutes Compound 64 of the present invention: LCMS: 500[M+H]+, RT =1.44 minutes Compound 65 of the present invention: LCMS: 526[M+H]+, RT =1.44 minutes Compound 66 of the present invention: LCMS: 542[M+H]+, RT = 1.60 minutes. Compound 67 of the present invention: LCMS: 543 [M+H] +, RT = 1.64 minutes. Compound 68 of the present invention: LCMS: 525 [M+H] +, RT = 1.48 minutes. Compound 69 of the present invention: LCMS: 541 [M+H] +, RT = 1.65 minutes. Compound 70 of the present invention: LCMS: 487 [M+H] +, RT = 1.62 minutes. Compound 71 of the present invention: LCMS: 503 [M+H] +, RT = 1.78 minutes. Compound 72 of the present invention: LCMS: 439 [M+H] +, RT = 1.59 minutes. Compound 73 of the present invention: LCMS: 455 [M+H] +, RT = 1.75 minutes. Compound 74 of the present invention: LCMS: 487[M+H]+, RT =1.64 minutes Compound 75 of the present invention: LCMS: 503[M+H]+, RT =1.79 minutes Compound 76 of the present invention: LCMS: 439[M+H]+, RT =1.60 minutes Compound 77 of the present invention: LCMS: 455[M+H]+, RT =1.77 minutes
[0123] Next, examples of the compound of the present invention that can be produced according to any of the production methods described in the Examples and the production methods described in this specification are shown below.
[0124] Formula (L-1) In the compound represented by the formula (hereinafter referred to as compound (L-1)), n is 0, and R 1 is a hydrogen atom, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX1).
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132] In the compound (L-1), n is 0 and R 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX4). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX5). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX6). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX7). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX8). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX9). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX10). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX11). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX12). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX13). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX14). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX15). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX16). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX17). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX18). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX22). 1 is a methyl group, and R 3b is a fluorine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX23). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX24). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX25). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX26). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX27). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX28). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX29). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX30). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX31). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX32). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX33). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX34). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX35). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX36). 1 is a methyl group, and R 3b is a chlorine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX40). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX41). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX42). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX43). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX44). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX45). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX46). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX47). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX48). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX49). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX50). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX51). 1 is a benzyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX52). 1 is a benzyl group, and R 3b is a chlorine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX53). 1 is a benzyl group, and R 3b is a chlorine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX54). 1 is a methyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX58). 1 is a methyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX59). 1 is a methyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX60). 1 is an ethyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX61). 1 is an ethyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX62). 1 is an ethyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX63). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX64). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX65). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX66). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX67). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX68). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX69). 1 is a benzyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX70). 1 is a benzyl group, and R 3b is a bromine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX71). 1 is a benzyl group, and R 3b is a bromine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX72). 1 is a methyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX76). 1 is a methyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX77). 1 is a methyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in Tables L1 to L13 (hereinafter referred to as compound group SX78). 1 is an ethyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX79). 1 is an ethyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX80). 1 is an ethyl group, and R 3b is an iodine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX81). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX82). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX83). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX84). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX85). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX86). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX87). 1 is a benzyl group, and R 3b is an iodine atom, and R 3cis a hydrogen atom, and Q is any of the substituents described in Tables L1 to L13 (hereinafter referred to as compound group SX88). 1 is a benzyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in Tables L1 to L13 (hereinafter referred to as compound group SX89). 1 is a benzyl group, and R 3b is an iodine atom, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX90). 1 is a methyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX94). 1 is a methyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX95). 1 is a methyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX96). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in Tables L1 to L13 (hereinafter referred to as compound group SX97). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX98). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX99). 1 is an isopropyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX100). 1 is an isopropyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX101). 1 is an isopropyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX102). 1 is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX103). 1 is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX104). 1is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX105). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX106). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX107). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX108). 1 is a methyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX112). 1 is a methyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX113). 1 is a methyl group, and R 3b is a difluoromethyl group, and R 3cis a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX114). 1 is an ethyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX115). 1 is an ethyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX116). 1 is an ethyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX117). 1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX118). 1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX119). 1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX120). 1 is a methylcyano group, and R 3bis a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX121). 1 is a methylcyano group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX122). 1 is a methylcyano group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX123). 1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX124). 1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX125). 1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3c is a hydrogen atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX126). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX130). 1is a methyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Tables L1] to L13] (hereinafter referred to as compound group SX131). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX132). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX133). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Tables L1] to L13] (hereinafter referred to as compound group SX134). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX135). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX136). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX137). 1is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX138). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX139). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX140). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX141). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX142). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX143). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX144). 1is a methyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX148). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX149). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX150). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX151). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX152). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX153). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX154). 1is an isopropyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX155). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX156). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX157). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX158). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX159). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX160). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX161).1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX162). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX166). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX167). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX168). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX169). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX170). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX171). 1is an isopropyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX172). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX173). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX174). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX175). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX176). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX177). 1 is a benzyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX178).1 is a benzyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX179). 1 is a benzyl group, and R 3b is a chlorine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX180). 1 is a methyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX184). 1 is a methyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX185). 1 is a methyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX186). 1 is an ethyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX187). 1 is an ethyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX188). 1is an ethyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX189). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX190). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX191). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX192). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX193). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX194). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX195).1 is a benzyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX196). 1 is a benzyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX197). 1 is a benzyl group, and R 3b is a bromine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX198). 1 is a methyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX202). 1 is a methyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX203). 1 is a methyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX204). 1 is an ethyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX205).1 is an ethyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX206). 1 is an ethyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX207). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX208). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX209). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX210). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX211). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3cis a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX212). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX213). 1 is a benzyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX214). 1 is a benzyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX215). 1 is a benzyl group, and R 3b is an iodine atom, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX216). 1 is a methyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX220). 1 is a methyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX221). 1 is a methyl group, and R 3bis a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX222). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX223). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX224). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX225). 1 is an isopropyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX226). 1 is an isopropyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX227). 1 is an isopropyl group, and R 3b is a trifluoromethyl group, and R 3cis a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX228). 1 is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX229). 1 is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX230). 1 is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX231). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX232). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX233). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX234). 1 is a methyl group, and R3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX238). 1 is a methyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX239). 1 is a methyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Tables L1] to L13] (hereinafter referred to as compound group SX240). 1 is an ethyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX241). 1 is an ethyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX242). 1 is an ethyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX243). 1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX244).1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX245). 1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX246). 1 is a methylcyano group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX247). 1 is a methylcyano group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX248). 1 is a methylcyano group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX249). 1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX250). 1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3cis a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX251). 1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3c is a fluorine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX252). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX256). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX257). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX258). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX259). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX260). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX261). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX262). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX263). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX264). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX265). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX266). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX267). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX268). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX269). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX270). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX274). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX275). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX276). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX277). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX278). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX279). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX280). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX281). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX282). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX283). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX284). 1 is a methylcyano group, and R 3b is a fluorine atom, and R3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX285). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX286). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX287). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX288). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX292). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX293). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX294). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX295). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX296). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX297). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX298). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX299). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX300). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX301). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX302). 1 is a methylcyano group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX303). 1 is a benzyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX304). 1 is a benzyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX305). 1 is a benzyl group, and R 3b is a chlorine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX306). 1 is a methyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX310). 1 is a methyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX311). 1 is a methyl group, and R 3b is a bromine atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX312). 1 is an ethyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX313). 1 is an ethyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX314). 1 is an ethyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX315). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX316). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX317). 1 is an isopropyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX318). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX319). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX320). 1 is a methylcyano group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX321). 1 is a benzyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX322). 1 is a benzyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX323). 1 is a benzyl group, and R 3b is a bromine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Tables L1] to L13] (hereinafter referred to as compound group SX324). 1 is a methyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX328). 1 is a methyl group, and R 3b is an iodine atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX329). 1 is a methyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX330). 1 is an ethyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX331). 1 is an ethyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX332). 1 is an ethyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX333). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX334). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX335). 1 is an isopropyl group, and R 3b is an iodine atom, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX336). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX337). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX338). 1 is a methylcyano group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX339). 1 is a benzyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX340). 1 is a benzyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX341). 1 is a benzyl group, and R 3b is an iodine atom, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX342). 1 is a methyl group, and R 3b is a trifluoromethyl group, and R3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX346). 1 is a methyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX347). 1 is a methyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX348). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX349). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX350). 1 is an ethyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX351). 1 is an isopropyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX352). 1 is an isopropyl group, and R3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX353). 1 is an isopropyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX354). 1 is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX355). 1 is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX356). 1 is a methylcyano group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX357). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX358). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3cis a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX359). 1 is a benzyl group, and R 3b is a trifluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX360). 1 is a methyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX364). 1 is a methyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Tables L1] to L13] (hereinafter referred to as compound group SX365). 1 is a methyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX366). 1 is an ethyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX367). 1 is an ethyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX368). 1 is an ethyl group, and R 3bis a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX369). 1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX370). 1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX371). 1 is an isopropyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX372). 1 is a methylcyano group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX373). 1 is a methylcyano group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX374). 1 is a methylcyano group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX375).1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX376). 1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX377). 1 is a benzyl group, and R 3b is a difluoromethyl group, and R 3c is a bromine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX378). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX382). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX383). 1 is a methyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX384). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX385).1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX386). 1 is an ethyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX387). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX388). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX389). 1 is an isopropyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX390). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX391). 1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX392).1 is a methylcyano group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX393). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX394). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX395). 1 is a benzyl group, and R 3b is a hydrogen atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX396). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX400). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX401). 1 is a methyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX402).1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX403). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX404). 1 is an ethyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX405). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX406). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX407). 1 is an isopropyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX408). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3cis an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX409). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX410). 1 is a methylcyano group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX411). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX412). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX413). 1 is a benzyl group, and R 3b is a fluorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX414). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX418). 1 is a methyl group, and R 3b is a chlorine atom, and R 3cis an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX419). 1 is a methyl group, and R 3b is a chlorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX420). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX421). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX422). 1 is an ethyl group, and R 3b is a chlorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX423). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX424). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c is an iodine atom, and Q is any of the substituents described in [Table L1] to [Table L13] (hereinafter referred to as compound group SX425). 1 is an isopropyl group, and R 3b is a chlorine atom, and R 3c...
Claims
1. Equation (I) 【Chemistry 1】 [During the ceremony, W represents an oxygen atom or a sulfur atom. R 1 This includes a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group D, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group E, a phenyl group which may be substituted with one or more substituents selected from group F, a 5 or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group F, and C(O)R 4 , C(O)OR 4 , or C(O)NR 4 R 5 This represents, R 4 and R 5 This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group F, a 5 or 6-membered heterocyclic group which may be substituted with one or more substituents selected from group F, or a hydrogen atom. R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropyl group, a cyclopropylmethyl group, or NR 6 R 7 and represents R 6 and R 7 This represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom, or R 6 and R 7 These may, together with the nitrogen atom to which they are bonded, form an azilidinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidyl group. n represents 0, 1, or 2. G 1 is a nitrogen atom or CR 3a This represents, G 2 is a nitrogen atom or CR 3b This represents, G 3 is a nitrogen atom or CR 3c This represents, G 4 is a nitrogen atom or CR 3d This represents, R 3a , R 3b , R 3c and R 3d OR are a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group H, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group J, a phenyl group which may be substituted with one or more substituents selected from group K, a 5 or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group K 8 , NR 8 R 9 , NR 8a R 9a , NR 10 NR 8 R 9 , NR 10 OR 9 , NR 9 C(O)R 11 , NR 10 NR 9 C(O)R 11 , NR 9 C(O)OR 12 , NR 10 NR 9 C(O)OR 12 , NR 9 C(O)NR 13 R 14 , NR 10 NR 9 C(O)NR 13 R 14 N=CHNR 13 R 14 N=S(O) p R 15 R 16 , C(O)R 11 , C(O)OR 17 , C(O)NR 13 R 14 , C(O)NR 9 S(O) 2 R 18 CR 19 =NOR 17 , NR 9 CR 10 =NOR 17 , S(O) m R 18 , represents a cyano group, a nitro group, a hydrogen atom, or a halogen atom, p represents 0 or 1, m represents 0, 1, or 2. R 8 This includes a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group L, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group M, a C3-C7 cycloalkenyl group which may be substituted with one or more substituents selected from group M, and group J 2 Phenyl groups, group J, which may be substituted with one or more more selected substituents. 2 A six-membered aromatic heterocyclic group, a hydrogen atom, or S(O) which may be substituted with one or more more selected substituents. 2 R 18 This represents, R 11 This includes C1-C6 chain hydrocarbon groups which may be substituted with one or more halogen atoms, C3-C7 cycloalkyl groups which may be substituted with one or more halogen atoms, (C3-C6 cycloalkyl)C1-C3 alkyl groups which may be substituted with one or more halogen atoms, and group J. 2 Phenyl groups, group J, which may be substituted with one or more more selected substituents. 2 A 5- or 6-membered aromatic heterocyclic group, which may be substituted with one or more more selected substituents, or a hydrogen atom, R 12 This is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl portion in the phenyl C1-C3 alkyl group belongs to group J}. 2 This represents} which may be substituted with one or more more selected substituents, R 13 This represents a C1-C6 alkyl group or hydrogen atom which may be substituted with one or more halogen atoms. R 14 This is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group L, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group M, and S(O) 2 R 18 , or represents a hydrogen atom, R 15 and R 16 This represents a C1-C6 alkyl group that is the same or different in phase and may be substituted with one or more halogen atoms. R 17 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from Group J 2 or a hydrogen atom, R 18 This is a C1-C6 chain hydrocarbon group, or group J, which may be substituted with one or more halogen atoms. 2 Represents a phenyl group which may be substituted with one or more more selected substituents, R 19 This is a C1-C6 chain hydrocarbon group, a halogen atom, OR which may be substituted with one or more halogen atoms. 20 , NR 21 R 22 , or represents a hydrogen atom, R 20 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, R 9 , R 10 , R 21 and R 22 This represents a C1-C6 chain hydrocarbon group, which may be the same or different in phase and may be substituted with one or more halogen atoms, or a hydrogen atom. R 8a and R 9a Together with the nitrogen atom to which they are bonded, they form a 3-7 member non-aromatic heterocyclic group which may be substituted with one or more substituents selected from group P. Q is Q 1 Or Q 2 This represents, 【Chemistry 2】 Z 1 NR 3j , representing an oxygen atom or a sulfur atom, Z 2 NR 3k , representing an oxygen atom or a sulfur atom, Q is Q 1 Z 1 NR 3j When representing X 1 is a nitrogen atom or CR 3e This represents X 2 is a nitrogen atom or CR 3f This represents X 3 is a nitrogen atom or CR 3g This represents, Q is Q 1 Z 1 If X represents an oxygen atom, 1 is a nitrogen atom or CR 3e This represents X 2 is a nitrogen atom or CR 3f This represents X 3 is a nitrogen atom or CR 3g This represents (however, X exists) 1 , X 2 and X 3 Not all of them represent nitrogen atoms.) Q is Q 1 Z 1 If X represents a sulfur atom, 1 is a nitrogen atom or CR 3e This represents X 2 is a nitrogen atom or CR 3f This represents X 3 is a nitrogen atom or CR 3g This represents (however, X exists) 1 , X 2 and X 3 Not all of them represent nitrogen atoms.) Q is Q 2 Z 2 NR 3k When representing X 1 is a nitrogen atom or CR 3e This represents X 2 is a nitrogen atom or CR 3f This represents X 4 is a nitrogen atom or CR 3h This represents, Q is Q 2 Z 2 If X represents an oxygen atom, 1 is a nitrogen atom or CR 3e This represents X 2 is a nitrogen atom or CR 3f This represents X 4 is a nitrogen atom or CR 3h This represents (however, X exists) 1 , X 2 and X 4 Not all of them represent nitrogen atoms.) Q is Q 2 Z 2 If X represents a sulfur atom, 1 is a nitrogen atom or CR 3e This represents X 2 is a nitrogen atom or CR 3f This represents X 4 is a nitrogen atom or CR 3h This represents (however, X exists) 1 , X 2 and X 4 Not all of them represent nitrogen atoms.) R 3j This includes a methyl group which may be substituted with one or more substituents selected from group T, a C2-C4 chain hydrocarbon group which may be substituted with one or more substituents selected from group U, a C5-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group V, and group K 2 C3-C7 cycloalkyl groups which may be substituted with one or more substituents selected from group X, phenyl groups which may be substituted with one or more substituents selected from group X, 5 or 6-membered aromatic heterocyclic groups which may be substituted with one or more substituents selected from group X, C(O)R 23 , C(O)OR 24 , C(O)NR 25 R 26 , C(O)NR 27 S(O) 2 R 28 CR 29 =NOR 24 , or S(O) k R 28 This represents, k represents 0, 1, or 2. R 23 This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group X, a 5 or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group X, or a hydrogen atom. R 24 This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group X, or a hydrogen atom. R 25 This represents a C1-C6 alkyl group or hydrogen atom which may be substituted with one or more halogen atoms. R 26 This refers to a C1-C6 chain hydrocarbon group, which may be substituted with one or more substituents selected from group V, and group K. 2 C3-C7 cycloalkyl groups, S(O) which may be substituted with one or more more selected substituents. v R 28 , or represents a hydrogen atom, v represents 0, 1, or 2. R 28 This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from group X. R 29 This is a C1-C6 chain hydrocarbon group, a halogen atom, OR which may be substituted with one or more halogen atoms. 30 , NR 31 R 32 , or represents a hydrogen atom, R 30 This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. R 27 , R 31 and R 32 This represents a C1-C6 chain hydrocarbon group, which may be the same or different in phase and may be substituted with one or more halogen atoms, or a hydrogen atom. R 3k C1-C6 chain hydrocarbon group, which may be substituted with one or more substituents selected from group Y, and group M 2 C3-C7 cycloalkyl groups, group A, which may be substituted with one or more more selected substituents. 2 Phenyl groups, group A, which may be substituted with one or more more selected substituents. 2 A 5 or 6-membered aromatic heterocyclic group, C(O)R, which may be substituted with one or more more selected substituents. 52 , C(O)OR 53 , C(O)NR 54 R 55 , C(O)NR 56 S(O) 2 R 57 CR 58 =NOR 53 , S(O) t R 57 , or represents a hydrogen atom, t represents 0, 1, or 2. R 52 This includes a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, and Group A. 2 Phenyl groups, group A, which may be substituted with one or more more selected substituents. 2 A 5- or 6-membered aromatic heterocyclic group, which may be substituted with one or more more selected substituents, or a hydrogen atom, R 53 C1-C6 chain hydrocarbon group, group A, which may be substituted with one or more halogen atoms. 2 A phenyl group or hydrogen atom which may be substituted with one or more more selected substituents, R 54 This represents a C1-C6 alkyl group or hydrogen atom which may be substituted with one or more halogen atoms. R 55 C1-C6 chain hydrocarbon group, which may be substituted with one or more substituents selected from group Y, and group M 2 C3-C7 cycloalkyl groups, S(O) which may be substituted with one or more more selected substituents. y R 28 , or represents a hydrogen atom, y represents 0, 1, or 2. R 57 This is a C1-C6 chain hydrocarbon group, or group A, which may be substituted with one or more halogen atoms. 2 Represents a phenyl group which may be substituted with one or more more selected substituents, R 58 This is a C1-C6 chain hydrocarbon group, a halogen atom, OR which may be substituted with one or more halogen atoms. 59 , NR 60 R 61 , or represents a hydrogen atom, R 59 This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. R 56 , R 60 and R 61 This represents a C1-C6 chain hydrocarbon group, which may be the same or different in phase and may be substituted with one or more halogen atoms, or a hydrogen atom. R 3e , R 3f , R 3g and R 3h These are the same or different, Group B 2 C1-C6 chain hydrocarbon groups, group D, which may be substituted with one or more more selected substituents. 2 C3-C7 cycloalkyl groups, group E, which may be substituted with one or more more selected substituents. 2 Phenyl groups, group E, which may be substituted with one or more more selected substituents. 2 A 5 or 6-membered aromatic heterocyclic group, OR which may be substituted with one or more more selected substituents. 33 , NR 33 R 34 , NR 33a R 34a , NR 35 NR 33 R 34 , NR 35 OR 34 , NR 34 C(O)R 36 , NR 35 NR 34 C(O)R 36 , NR 34 C(O)OR 37 , NR 35 NR 34 C(O)OR 37 , NR 34 C(O)NR 38 R 39 , NR 35 NR 34 C(O)NR 38 R 39 N=CHNR 38 R 39 N=S(O) q R 40 R 41 , C(O)R 36 , C(O)OR 42 , C(O)NR 38 R 39 , C(O)NR 34 S(O) 2 R 43 CR 44 =NOR 42 , NR 34 CR 35 =NOR 42 , S(O) r R 43 , represents a cyano group, a nitro group, a halogen atom, or a hydrogen atom, q represents 0 or 1, r represents 0, 1, or 2. R 33 Group B 2 C1-C6 chain hydrocarbon groups, group D, which may be substituted with one or more more selected substituents. 2 C3-C7 cycloalkyl groups, group D, which may be substituted with one or more more selected substituents. 2 C3-C7 cycloalkenyl groups, group E, which may be substituted with one or more more selected substituents. 2 Phenyl groups, group E, which may be substituted with one or more more selected substituents. 2 A six-membered aromatic heterocyclic group, a hydrogen atom, or S(O) which may be substituted with one or more more selected substituents. 2 R 43 This represents, R 36 This includes a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, and group E. 2 Phenyl groups, group E, which may be substituted with one or more more selected substituents. 2 A 5- or 6-membered aromatic heterocyclic group, which may be substituted with one or more more selected substituents, or a hydrogen atom, R 37 This is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl portion in the phenyl C1-C3 alkyl group belongs to group E 2 This represents} which may be substituted with one or more more selected substituents, R 38 This represents a C1-C6 alkyl group or hydrogen atom which may be substituted with one or more halogen atoms. R 39 Group B 2 C1-C6 chain hydrocarbon groups, group D, which may be substituted with one or more more selected substituents. 2 C3-C7 cycloalkyl groups, S(O) which may be substituted with one or more more selected substituents. 2 R 43 , or represents a hydrogen atom, R 40 and R 41 This represents a C1-C6 alkyl group that is the same or different in phase and may be substituted with one or more halogen atoms. R 42 This refers to a C1-C6 chain hydrocarbon group, group E, which may be substituted with one or more halogen atoms. 2 A phenyl group or hydrogen atom which may be substituted with one or more more selected substituents, R 43 This is a C1-C6 chain hydrocarbon group, or group E, which may be substituted with one or more halogen atoms. 2 Represents a phenyl group which may be substituted with one or more more selected substituents, R 44 This is a C1-C6 chain hydrocarbon group, a halogen atom, OR which may be substituted with one or more halogen atoms. 45 , NR 46 R 47 , or represents a hydrogen atom, R 45 This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. R 34 , R 35 , R 46 and R 47 This represents a C1-C6 chain hydrocarbon group, which may be the same or different in phase and may be substituted with one or more halogen atoms, or a hydrogen atom. R 33a and R 34a Together with the nitrogen atoms to which they are bonded, they form group F 2 It forms a 3-7 member non-aromatic heterocyclic group which may be substituted with one or more more selected substituents. Group D: C3-C6 cycloalkyl groups that may be substituted with one or more substituents selected from the group consisting of halogen atoms and C1-C3 alkyl groups, C1-C6 alkoxy groups that may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups that may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups that may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups that may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups that may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups that may be substituted with one or more halogen atoms, Group L 2 Phenyl groups, group L, which may be substituted with one or more more selected substituents. 2 A group consisting of a five- or six-membered aromatic heterocyclic group, a hydroxyl group, a cyano group, and a halogen atom, which may be substituted with one or more more selected substituents. Group E: A group consisting of C1-C6 alkyl groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, and halogen atoms. Group F: A group consisting of C1-C6 alkyl groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylamino groups which may be substituted with one or more halogen atoms, di(C1-C6 alkyl)amino groups which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, amino groups, cyano groups, nitro groups, and halogen atoms. Group H: A group consisting of C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C3-C6 alkenyloxy groups which may be substituted with one or more halogen atoms, C3-C6 alkynyloxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups which may be substituted with one or more halogen atoms, cyano groups, hydroxyl groups, and halogen atoms. Group J: A group consisting of C1-C6 chain hydrocarbon groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C3-C6 alkenyloxy groups which may be substituted with one or more halogen atoms, C3-C6 alkynyloxy groups which may be substituted with one or more halogen atoms, halogen atoms, oxo groups, hydroxyl groups, cyano groups, and nitro groups. Group K: C1-C6 alkyl groups which may be substituted with one or more halogen atoms, Group J 2 A 5 or 6-membered aromatic heterocyclic group, OR which may be substituted with one or more more selected substituents. 49 , NR 48 R 49 , C(O)R 49 , C(O)NR 48 R 49 OC(O)R 48 , OC(O)OR 48 , NR 49 C(O)R 48 , NR 49 C(O)OR 48 , C(O)OR 49 A group consisting of halogen atoms, nitro groups, cyano groups, and amino groups. R 48 This represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms. R 49 This represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom. Group L: C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, Group J 2 Phenyl groups, group J, which may be substituted with one or more more selected substituents. 2 A 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more more selected substituents, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, and group H 2 A 3-7 member non-aromatic heterocyclic group, amino group, or NHR which may be substituted with one or more more selected substituents. 50 , NR 50 R 51 A group consisting of halogen atoms and cyano groups. R 50 and R 51 This represents a C1-C6 alkyl group that is the same or different in phase and may be substituted with one or more halogen atoms. Group M: A group consisting of C1-C6 alkyl groups, halogen atoms, and cyano groups, which may be substituted with one or more halogen atoms. Group P: A group consisting of C1-C6 chain hydrocarbon groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C3-C6 alkenyloxy groups which may be substituted with one or more halogen atoms, C3-C6 alkynyloxy groups which may be substituted with one or more halogen atoms, halogen atoms, oxo groups, hydroxyl groups, cyano groups, and nitro groups. Group T: A group consisting of C3-C6 cycloalkyl groups which may be substituted with one or more substituents selected from the group consisting of a fluorine atom and a C1-C3 alkyl group, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, and halogen atoms. Group U: A group consisting of a fluorine atom and one or more substituents selected from the group consisting of a fluorine atom and a C1-C3 alkyl group, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, a sulfanyl group, and a fluorine atom. Group V: A group consisting of C3-C6 cycloalkyl groups which may be substituted with one or more substituents selected from the group consisting of halogen atoms and C1-C3 alkyl groups, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, cyano groups, and halogen atoms. Group X: A group consisting of C1-C6 alkyl groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylamino groups which may be substituted with one or more halogen atoms, di(C1-C6 alkyl)amino groups which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, amino groups, cyano groups, nitro groups, and halogen atoms. Group Y: A group consisting of C3-C6 cycloalkyl groups which may be substituted with one or more substituents selected from the group consisting of halogen atoms and C1-C3 alkyl groups, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, cyano groups, and halogen atoms. Group A 2 : A group consisting of C1-C6 alkyl groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylamino groups which may be substituted with one or more halogen atoms, di(C1-C6 alkyl)amino groups which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, amino groups, cyano groups, nitro groups, and halogen atoms. Group B 2 : C3-C6 cycloalkyl groups which may be substituted with one or more substituents selected from the group consisting of halogen atoms and C1-C3 alkyl groups, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, cyano groups, and halogen atoms. Group D 2 : A group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, and halogen atoms. Group E 2 : A group consisting of C1-C6 alkyl groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylamino groups which may be substituted with one or more halogen atoms, di(C1-C6 alkyl)amino groups which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, amino groups, cyano groups, nitro groups, and halogen atoms. Group F 2 : A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group, and a nitro group. Group H 2 : A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, and halogen atoms. Group J 2 : A C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, an amino group, NHR 50 , NR 50 R 51 , C(O)R 50 OC(O)R 50 , C(O)OR 50 A group consisting of cyano groups, nitro groups, and halogen atoms. Group K 2 : A group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, and a fluorine atom. Group L 2 : A group consisting of C1-C6 alkyl groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylamino groups which may be substituted with one or more halogen atoms, di(C1-C6 alkyl)amino groups which may be substituted with one or more halogen atoms, C2-C6 alkylcarbonyl groups which may be substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl groups which may be substituted with one or more halogen atoms, hydroxyl groups, sulfanyl groups, amino groups, cyano groups, nitro groups, and halogen atoms. Group M 2 : A group consisting of a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, and halogen atoms. The compound shown or its N oxide.
2. G 1 CR 3a G 2 CR 3b G 3 CR 3c G 4 is a nitrogen atom or CR 3d The compound or its N oxide as described in claim 1.
3. G 1 CR 3a G 2 CR 3b G 3 CR 3c G 4 CR 3d The compound or its N oxide as described in claim 1.
4. Q is Q 1 Q 1 In Z 1 , X 1 , X 2 and X 3 The combination is, Z 1 X is an oxygen atom, 1 X is a nitrogen atom, 2 CR 3f X 3 CR 3g The combinations that are; Z 1 X is an oxygen atom, 1 CR 3e X 2 X is a nitrogen atom, 3 CR 3g The combinations that are; Z 1 X is an oxygen atom, 1 CR 3e X 2 CR 3f X 3 Combinations in which the atom is nitrogen; Z 1 X is a sulfur atom, 1 CR 3e X 2 X is a nitrogen atom, 3 CR 3g The combinations that are; Z 1 X is a sulfur atom, 1 X is a nitrogen atom, 2 CR 3f X 3 CR 3g The combinations that are; Z 1 NR 3j X 1 X is a nitrogen atom, 2 CR 3f X 3 CR 3g The combinations that are; Z 1 NR 3j X 1 CR 3e X 2 X is a nitrogen atom, 3 CR 3g A combination that is; or, Z 1 NR 3j X 1 CR 3e X 2 CR 3f X 3 A compound according to any one of claims 1 to 3, or its N oxide, wherein the combination is a nitrogen atom.
5. Q is Q 2 Q 2 In Z 2 , X 1 , X 2 and X 4 The combination is, Z 2 X is an oxygen atom, 1 X is a nitrogen atom, 2 CR 3f X 4 CR 3h The combinations that are; Z 2 X is an oxygen atom, 1 CR 3e X 2 X is a nitrogen atom, 4 CR 3h The combinations that are; Z 2 X is an oxygen atom, 1 CR 3e X 2 CR 3f X 4 Combinations in which the atom is nitrogen; Z 2 NR 3k X 1 X is a nitrogen atom, 2 CR 3f X 4 CR 3h The combinations that are; Z 2 NR 3k X 1 CR 3e X 2 X is a nitrogen atom, 4 CR 3h The combinations that are; Z 2 NR 3k X 1 CR 3e X 2 CR 3f X 4 Combinations in which the atom is nitrogen; Z 2 NR 3k X 1 CR 3e X 2 CR 3f X 4 CR 3h A combination that is; or, Z 2 NR 3k X 1 X is a nitrogen atom, 2 X is a nitrogen atom, 4 CR 3h A combination of the compound or its N oxide according to any one of claims 1 to 3.
6. R 2 The compound according to any one of claims 1 to 3, or its N oxide, wherein the N oxide is an ethyl group.
7. A compound according to any one of claims 1 to 3, wherein W is an oxygen atom, or its N oxide.
8. A pest control composition containing the compound described in any one of claims 1 to 3 or its N oxide.
9. A composition containing one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound or its N oxide described in any one of claims 1 to 3: Group (a): A group consisting of insecticidal components, acaricidal components, and nematicidal components; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): Repellent components.
10. A method for controlling harmful arthropods, comprising applying an effective amount of the compound or its N oxide described in any one of claims 1 to 3 to a harmful arthropod or to the habitat of a harmful arthropod.
11. A method for controlling harmful arthropods, comprising applying an effective amount of the composition described in Claim 9 to a harmful arthropod or to a habitat of a harmful arthropod.
12. Seeds or vegetative reproductive organs that retain an effective amount of the compound or its N oxide according to any one of claims 1 to 3.
13. A seed or vegetative reproductive organ holding an effective amount of the composition described in Claim 9.
14. Formula (II) 【Transformation 3】 [In the formula, the symbols have the same meaning as in Claim 1.] The compound or salt thereof indicated by [the symbol].