Acrylic acid ester derivatives, their uses and their manufacturing intermediates

Abstract

The present invention provides a compound that has an excellent pest-controlling effect and that is represented by formula (I) [in the formula, L represents an oxygen atom or CH2, E represents a C2-C10 chain hydrocarbon group or the like, R1 represents a C1-C3 chain hydrocarbon group or the like, R2 represents a C1-C3 chain hydrocarbon group or the like, and n represents 0, 1, 2, or 3], or an N-oxide thereof, or an agriculturally acceptable salt thereof.

Description

[Technical Field]

[0001] This patent application claims priority under the Paris Convention to and the benefit of Japanese Patent Application Nos. 2019-120901 (filed June 28, 2019) and 2020-015184 (filed January 31, 2020), the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to an acrylic ester derivative, its uses, and a production intermediate thereof. [Background technology]

[0003] Patent Document 1 describes an acrylic acid ester derivative. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] European Patent Application Publication No. 212859 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide a compound having excellent pesticidal activity against pests. [Means for solving the problem]

[0006] The present inventors have conducted research to find a compound having excellent control activity against pests, and as a result have found that a compound represented by the following formula (I) has excellent control activity against pests. That is, the present invention is as follows. [1] Formula (I): [ka] [During the ceremony, L represents an oxygen atom or CH2; E is a methyl group substituted with one or more substituents selected from group A, a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R 5 represents NS(O)2-, R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different, R 2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; R 3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C} or a hydrogen atom, R 4 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group C}, R 5represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom, R 6 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C} or a hydrogen atom, R 3 and R 5 is R 3 and R 5 and may be taken together with the nitrogen atom to which they are bonded to form a 4- to 7-membered non-aromatic heterocycle {the 4- to 7-membered non-aromatic heterocycle may have one or more substituents selected from group B}. Group A: OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11 C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13 , N.R. 12 S(O)2R 13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group and a nitro group. R 11 and R 12 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group F} or a hydrogen atom, R 13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group D, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group E, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group or a 3- to 8-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}, R 14 , R 15 and R 16 are the same or different and represent a C1-C6 chain hydrocarbon group or a phenyl group, m represents 0, 1 or 2. Group B: C1-C6 chain hydrocarbon groups optionally substituted with one or more substituents selected from Group D, OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13 , N.R. 12 S(O)2R 13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16 the group consisting of a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, an oxo group, a thioxo group, a halogen atom, a cyano group and a nitro group. Group C: a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11 C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13 , N.R. 12 S(O)2R13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16 , a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group and a nitro group. Group D: C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group}, OR 17 , S(O) m R 19 , OS(O)2R 19 , C(O)R 17 , C(O)OR 17 ,OC(O)R 17 ,OC(O)OR 17 , OC(O)NR 17 R 18 , N.R. 17 C(O)NR 18 R 19 , N.R. 17 R 18 , C(O)NR 17 R 18 , S(O)NR 17 R 18 , N.R. 18 C(O)R 17 , N.R. 18 C(O)OR 19 , N.R. 18 S(O)2R 19 , C(R 18 )=N-OR 17 , ON=CR 17 R 19 , SiR 14 R 15 R 16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, and a 3- to 8-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}. R 17 and R 18 are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group} or a hydrogen atom, R 19 represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, or a 3- to 8-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group}. Group E: C1-C6 chain hydrocarbon groups, C3-C6 cycloalkyl groups {the C1-C6 chain hydrocarbon groups and the C3-C6 cycloalkyl groups may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups}, OR 17 , S(O) m R 19 , OS(O)2R 19 , C(O)R 17 , C(O)OR 17 ,OC(O)R 17 ,OC(O)OR 17 , OC(O)NR 17 R 18 , N.R. 17 C(O)NR 18 R 19 , N.R.17 R 18 , C(O)NR 17 R 18 , S(O)NR 17 R 18 , N.R. 18 C(O)R 17 , N.R. 18 C(O)OR 19 , N.R. 18 S(O)2R 19 , C(R 18 )=N-OR 17 , ON=CR 17 R 19 , SiR 14 R 15 R 16 , a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, and a 3- to 8-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}. Group F: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group and a C1-C6 alkylthio group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a halogen atom, a cyano group, a nitro group and a hydroxy group. or an N-oxide or an agriculturally acceptable salt thereof (hereinafter referred to as the compound of the present invention). [2] The compound according to [1], wherein E is a methyl group substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, or an N-oxide or an agriculturally acceptable salt thereof. [3] E is R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R4 S(O)2- or R 3 R 5 The compound according to [1], or an N-oxide or an agriculturally acceptable salt thereof, wherein NS(O)2-. [4] E is R 3 R 5 The compound according to [1], which is NC(O)-, or an N-oxide or an agriculturally acceptable salt thereof. [5] R 1

[0023] The compound according to any one of [1] to [4], wherein is a methyl group or a chlorine atom, n is 0, and L is an oxygen atom, or an N-oxide or an agriculturally acceptable salt thereof. [6] A pest control composition containing the compound according to any one of [1] to [5], or an N-oxide or an agriculturally acceptable salt thereof, and an inert carrier (hereinafter referred to as the composition of the present invention). [7] A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and a compound according to any one of [1] to [5], or an N-oxide or an agriculturally acceptable salt thereof: Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients; Group (b): Fungicidally active ingredients; Group (c): Plant growth regulating components; Group (d): repellent ingredients. [8] A method for controlling pests, which comprises treating a plant or soil with an effective amount of the compound according to any one of [1] to [5], or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to [7]. [9] A method for controlling soybean rust fungus having an F129L amino acid substitution in mitochondrial cytochrome b protein, comprising applying an effective amount of the compound according to any one of [1] to [5], or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to [7] to soybeans or soil in which soybeans are grown.

[10] Use of the compound according to any one of [1] to [5], or an N-oxide or agriculturally acceptable salt thereof, or the composition according to [7] for controlling pests.

[11] A seed or a vegetative reproductive organ carrying an effective amount of the compound according to any one of [1] to [5], or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to [7].

[12] Formula (II): [ka] [During the ceremony, L represents an oxygen atom or CH2; R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different, R 2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom. A compound represented by the formula (hereinafter referred to as intermediate A).

[13] R 1 is a methyl group or a chlorine atom, and n is 0.

[14] Formula (III): [ka] [During the ceremony, L represents an oxygen atom or CH2; E is a methyl group substituted with one or more substituents selected from group A, a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R 5 represents NS(O)2-, R 1represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different, R 2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; R 3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C} or a hydrogen atom, R 4 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group C}, R 5 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom, R 6 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C} or a hydrogen atom, R 3 and R 5 is R 3 and R 5and may be taken together with the nitrogen atom to which they are bonded to form a 4- to 7-membered non-aromatic heterocycle {the 4- to 7-membered non-aromatic heterocycle may have one or more substituents selected from group B}. Group A: OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11 C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13 , N.R. 12 S(O)2R 13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16 , a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group and a nitro group. R 11 and R 12are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group F} or a hydrogen atom, R 13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group D, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group E, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group or a 3- to 8-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}, R 14 , R 15 and R 16 are the same or different and represent a C1-C6 chain hydrocarbon group or a phenyl group, m represents 0, 1 or 2. Group B: C1-C6 chain hydrocarbon groups optionally substituted with one or more substituents selected from Group D, OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11 C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13, N.R. 12 S(O)2R 13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16 the group consisting of a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, an oxo group, a thioxo group, a halogen atom, a cyano group and a nitro group. Group C: a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11 C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13 , N.R. 12 S(O)2R 13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group and a nitro group. Group D: C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group}, OR 17 , S(O) m R 19 , OS(O)2R 19 , C(O)R 17 , C(O)OR 17 ,OC(O)R 17 ,OC(O)OR 17 , OC(O)NR 17 R 18 , N.R. 17 C(O)NR 18 R 19 , N.R. 17 R 18 , C(O)NR 17 R 18 , S(O)NR 17 R 18 , N.R. 18 C(O)R 17 , N.R. 18 C(O)OR 19 , N.R. 18 S(O)2R 19 , C(R 18 )=N-OR 17 , ON=CR 17 R 19 , SiR 14 R 15 R 16 , a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, and a 3- to 8-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}. R 17 and R18 are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group} or a hydrogen atom, R 19 represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, or a 3- to 8-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group}. Group E: C1-C6 chain hydrocarbon groups, C3-C6 cycloalkyl groups {the C1-C6 chain hydrocarbon groups and the C3-C6 cycloalkyl groups may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups}, OR 17 , S(O) m R 19 , OS(O)2R 19 , C(O)R 17 , C(O)OR 17 ,OC(O)R 17 ,OC(O)OR 17 , OC(O)NR 17 R 18 , N.R. 17 C(O)NR 18 R 19 , N.R. 17 R 18 , C(O)NR 17 R 18 , S(O)NR 17 R 18 , N.R. 18 C(O)R 17 , N.R. 18 C(O)OR 19 , N.R. 18 S(O)2R19 , C(R 18 )=N-OR 17 , ON=CR 17 R 19 , SiR 14 R 15 R 16 , a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, and a 3- to 8-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}. Group F: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group and a C1-C6 alkylthio group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a halogen atom, a cyano group, a nitro group and a hydroxy group. A compound represented by the formula (hereinafter referred to as intermediate B).

[15] The compound according to

[14] , wherein E is a methyl group substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A.

[16] E is R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R 5 The compound according to

[14] , which is NS(O)2-.

[17] E is R 3 R 5 The compound according to

[14] , wherein N—C(O)—.

[18] R 1 The compound according to any one of

[14] to

[17] , wherein is a methyl group or a chlorine atom, n is 0, and L is an oxygen atom.

[19] Formula (IV): [ka] [During the ceremony, E is a methyl group substituted with one or more substituents selected from group A, a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R 5 represents NS(O)2-, n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different, R 2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; R 3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C} or a hydrogen atom, R 4 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group C}, R 5represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom, R 6 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, a 5- to 10-membered aromatic heterocyclic group {the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C} or a hydrogen atom, R 3 and R 5 is R 3 and R 5 and may be taken together with the nitrogen atom to which they are bonded to form a 4- to 7-membered non-aromatic heterocycle {the 4- to 7-membered non-aromatic heterocycle may have one or more substituents selected from group B}. Group A: OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11 C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13 , N.R. 12 S(O)2R 13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group and a nitro group. R 11 and R 12 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group F} or a hydrogen atom, R 13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group D, a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group E, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group or a 3- to 8-membered non-aromatic heterocyclic group {the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}, R 14 , R 15 and R 16 are the same or different and represent a C1-C6 chain hydrocarbon group or a phenyl group, m represents 0, 1 or 2. Group B: C1-C6 chain hydrocarbon groups optionally substituted with one or more substituents selected from Group D, OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13 , N.R. 12 S(O)2R 13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16 the group consisting of a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, an oxo group, a thioxo group, a halogen atom, a cyano group and a nitro group. Group C: a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group D, OR 11 , S(O) m R 13 , OS(O)2R 13 , C(O)R 11 , C(O)OR 11 ,OC(O)R 11 ,OC(O)OR 11 , OC(O)NR 11 R 12 , N.R. 11 C(O)NR 12 R 13 , N.R. 11 R 12 , C(O)NR 11 R 12 , S(O)NR 11 R 12 , N.R. 12 C(O)R 11 , N.R. 12 C(O)OR 13 , N.R. 12 S(O)2R13 , C(R 12 )=N-OR 11 , ON=CR 11 R 13 , SiR 14 R 15 R 16 , a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from Group E}, a halogen atom, a cyano group and a nitro group. Group D: C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group}, OR 17 , S(O) m R 19 , OS(O)2R 19 , C(O)R 17 , C(O)OR 17 ,OC(O)R 17 ,OC(O)OR 17 , OC(O)NR 17 R 18 , N.R. 17 C(O)NR 18 R 19 , N.R. 17 R 18 , C(O)NR 17 R 18 , S(O)NR 17 R 18 , N.R. 18 C(O)R 17 , N.R. 18 C(O)OR 19 , N.R. 18 S(O)2R 19 , C(R 18 )=N-OR 17 , ON=CR 17 R 19 , SiR 14 R 15 R 16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, and a 3- to 8-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}. R 17 and R 18 are the same or different and represent a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, a 3- to 8-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group} or a hydrogen atom, R 19 represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5- or 6-membered aromatic heterocyclic group, or a 3- to 8-membered non-aromatic heterocyclic group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from the group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group}. Group E: C1-C6 chain hydrocarbon groups, C3-C6 cycloalkyl groups {the C1-C6 chain hydrocarbon groups and the C3-C6 cycloalkyl groups may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups}, OR 17 , S(O) m R 19 , OS(O)2R 19 , C(O)R 17 , C(O)OR 17 ,OC(O)R 17 ,OC(O)OR 17 , OC(O)NR 17 R 18 , N.R. 17 C(O)NR 18 R 19 , N.R.17 R 18 , C(O)NR 17 R 18 , S(O)NR 17 R 18 , N.R. 18 C(O)R 17 , N.R. 18 C(O)OR 19 , N.R. 18 S(O)2R 19 , C(R 18 )=N-OR 17 , ON=CR 17 R 19 , SiR 14 R 15 R 16 , a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a 5- to 6-membered aromatic heterocyclic group, and a 3- to 8-membered non-aromatic heterocyclic group {the phenoxy group, the phenyl group, the naphthyl group, the 5- to 6-membered aromatic heterocyclic group, and the 3- to 8-membered non-aromatic heterocyclic group are optionally substituted with one or more substituents selected from group F}. Group F: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group and a C1-C6 alkylthio group {the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group}, a halogen atom, a cyano group, a nitro group and a hydroxy group. A compound represented by the formula (hereinafter referred to as intermediate C).

[20] The compound according to

[19] , wherein n is 0 and E is a methyl group substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A.

[21] n is 0 and E is R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R5 The compound according to

[19] , which is NS(O)2-.

[22] n is 0 and E is R 3 R 5 The compound according to

[19] , wherein N—C(O)—.

[23] Formula (VI): [ka] [During the ceremony, L represents an oxygen atom or CH2; R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; R 2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different. A compound represented by the formula (hereinafter referred to as intermediate D).

[24] R 1 is a methyl group or a chlorine atom, and n is 0. [Effects of the Invention]

[0007] The present invention makes it possible to control pests. DETAILED DESCRIPTION OF THE INVENTION

[0008] The substituents in the present invention will be explained. A halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. When a substituent has two or more halogen atoms, these halogen atoms 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 methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, and decyl groups. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3-butenyl, 4-pentenyl, 5-hexenyl, and 9-decenyl groups. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group, a 5-hexynyl group, and a 9-decynyl group.

[0009] Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups. Examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, and a hexylthio group.

[0010] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.

[0011] Aryl groups include, for example, phenyl, indenyl, indanyl, naphthyl, and tetrahydronaphthyl groups. Examples of aromatic heterocyclic groups include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, indazolyl, benzimidazolyl, imidazopyridyl, benzothiophenyl, benzofuranyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl groups. Examples of non-aromatic heterocyclic groups include aziridinyl, oxiranyl, thiiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, piperidyl, pyranyl, tetrahydropyranyl, tetrahydrothiopyranyl, azepanyl, oxepanyl, thiepanyl, pyrazolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, thiazolinyl, oxazolidinyl, thiazolidinyl, isoxazolinyl, isoxazolidinyl, isothiazolinyl, isothiazolidinyl, morpholinyl, thiomorpholinyl, and piperazinyl.

[0012] The terms used in this specification will be explained below. Soybean rust fungus with the F129L amino acid substitution in the mitochondrial cytochrome b protein is a soybean rust fungus (scientific name: Phakopsora pachyrhizi) that has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein, resulting in the F129L amino acid substitution, and is therefore resistant to QoI fungicides.

[0013] The compounds of the present invention, Intermediate A, Intermediate B, Intermediate C, and Intermediate D may exist as one or more stereoisomers. Stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0014] Compound N of the present invention or its N-oxide may form an acid addition salt such as a hydrochloride, sulfate, nitrate, phosphate, acetate, or benzoate when mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, or benzoic acid.

[0015] The following compounds are examples of the compound N of the present invention.

[0016] [Embodiment 1] Compound N of the present invention, wherein n is 0. [Aspect 2] In aspect 1, R 1 is a methyl group or a chlorine atom. [Aspect 3] In aspect 1, R 1 is a methyl group. [Aspect 4] The compound of Aspect 1, wherein L is an oxygen atom. [Aspect 5] The compound according to aspect 2, wherein L is an oxygen atom. [Aspect 6] The compound according to aspect 3, wherein L is an oxygen atom. [Aspect 7] In aspect 1, R 1 A compound in which the atom is chlorine. [Embodiment 8] A compound in embodiment 1, wherein L is CH2. [Aspect 9] A compound in aspect 2, wherein L is CH2. [Aspect 10] The compound of aspect 3, wherein L is CH2. [Aspect 11] A compound according to any one of Aspects 1 to 10 or Compound N of the present invention, wherein E is a methyl group substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. [Aspect 12] A compound in any one of Aspects 1 to 10 or Compound N of the present invention, wherein E is a methyl group substituted with one or more substituents selected from Group A. [Aspect 13] A compound according to any one of Aspects 1 to 10 or Compound N of the present invention, wherein E is a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. [Aspect 14] In any one of Aspects 1 to 10 or the compound N of the present invention, E is R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R 5 A compound that is NS(O)2-. [Aspect 15] In any one of Aspects 1 to 10 or the compound N of the present invention, E is R 3 R 5 A compound that is NC(O)-. [Aspect 16] In any of Aspects 1 to 10 or Compound N of the present invention, E is a methyl group substituted with one or more substituents selected from Group J, a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group J, or R 3 R 5 NC(O)- and R 3 is a C1-C5 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more halogen atoms, and R 5 is a methyl group, a methoxy group, or a hydrogen atom, and R 3 and R 5 But R 3 and R 5 and a compound which may form a 5- or 6-membered non-aromatic heterocyclic group together with the nitrogen atom to which they are bonded. Group J: A group consisting of OCH3, Si(CH3)3, a C3-C6 cycloalkyl group, a cyano group, a halogen atom, a phenyl group, and a 5- to 6-membered aromatic heterocyclic group {the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group consisting of a trifluoromethyl group, a halogen atom, and a cyano group}. [Aspect 17] The compound in Aspect 16, wherein E is a methyl group substituted with one or more substituents selected from Group J, or a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group J. [Embodiment 18] In embodiment 16, E is R 3 R 5NC(O)- and R 3 is a C1-C5 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more halogen atoms, and R 5 is a methyl group, a methoxy group, or a hydrogen atom. [Embodiment 19] In embodiment 16, E is R 3 R 5 NC(O)- and R 3 and R 5 But R 3 and R 5 and a compound which may form a 5- or 6-membered non-aromatic heterocyclic group together with the nitrogen atom to which they are bonded. [Aspect 20] In any of Aspects 1 to 10 or Compound N of the present invention, E is a methyl group substituted with one or more substituents selected from Group K, a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group K, or R 3 R 5 NC(O)- and R 3 is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more halogen atoms, and R 5 is a methyl group, a methoxy group, or a hydrogen atom, and R 3 and R 5 But R 3 and R 5 and a compound which may form a 5- or 6-membered non-aromatic heterocyclic group together with the nitrogen atom to which they are bonded. Group K: a group consisting of OCH3, Si(CH3)3, a C3-C6 cycloalkyl group, a cyano group, a halogen atom, a 3- to 6-membered non-aromatic heterocyclic group, a phenyl group, and a 5- to 6-membered aromatic heterocyclic group {the C3-C6 cycloalkyl group, the 3- to 6-membered non-aromatic heterocyclic group, the phenyl group, and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group consisting of a trifluoromethyl group, a halogen atom, and a cyano group}. [Aspect 21] A compound in any one of Aspects 1 to 10 or Compound N of the present invention, wherein E is a methyl group substituted with one or more substituents selected from Group K, or a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group K. [Aspect 22] A compound according to any one of Aspects 1 to 10 or Compound N of the present invention, wherein E is a methyl group substituted with one or more substituents selected from Group K. [Aspect 23] A compound according to any one of Aspects 1 to 10 or Compound N of the present invention, wherein E is a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group K. [Aspect 24] A compound according to any one of Aspects 1 to 10 or Compound N of the present invention, wherein E is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Aspect 25] In any one of Aspects 1 to 10 or the present compound N, E is R 3 R 5 NC(O)- and R 3 is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more halogen atoms, and R 5 is a methyl group, a methoxy group, or a hydrogen atom, and R 3 and R 5 But R 3 and R 5 and a compound which may form a 5- or 6-membered non-aromatic heterocyclic group together with the nitrogen atom to which they are bonded. [Aspect 26] In any one of Aspects 1 to 10 or the compound N of the present invention, E is R 3 R 5 NC(O)- and R 3 and R 5 But R 3 and R 5 and a compound which may form a 5- or 6-membered non-aromatic heterocyclic group together with the nitrogen atom to which they are bonded.

[0017] Examples of intermediate A include the following compounds.

[0018] [Aspect A1] A compound in which n is 0 in Intermediate A. [Aspect A2] In aspect A1, R 1 is a methyl group or a chlorine atom. [Aspect A3] In Aspect A1, R 1 is a methyl group. [Aspect A4] The compound in Aspect A1, wherein L is an oxygen atom. [Aspect A5] The compound in Aspect A2, wherein L is an oxygen atom. [Aspect A6] The compound in Aspect A3, wherein L is an oxygen atom. [Aspect A7] In Aspect A1, R 1 A compound in which the atom is chlorine. [Aspect A8] The compound in Aspect A7, wherein L is an oxygen atom. [Aspect A9] The compound in Aspect A1, wherein L is CH2. [Aspect A10] The compound in Aspect A2, wherein L is CH2. [Aspect A11] The compound in Aspect A3, wherein L is CH2. [Aspect A12] The compound in Aspect A7, wherein L is CH2.

[0019] Examples of intermediate B include the following compounds:

[0020] [Aspect B1] A compound in which n is 0 in Intermediate B. [Aspect B2] In aspect B1, R 1 is a methyl group or a chlorine atom. [Aspect B3] In aspect B1, R 1 is a methyl group. [Aspect B4] The compound in Aspect B1, wherein L is an oxygen atom. [Aspect B5] The compound in Aspect B2, wherein L is an oxygen atom. [Aspect B6] The compound in Aspect B3, wherein L is an oxygen atom. [Aspect B7] A compound in any one of Aspects B1 to B6 or Intermediate B, wherein E is a methyl group substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. [Aspect B8] A compound in any one of Aspects B1 to B6 or Intermediate B, wherein E is a methyl group substituted with one or more substituents selected from Group A. [Aspect B9] A compound in any one of Aspects B1 to B6 or Intermediate B, wherein E is a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. [Aspect B10] In any of Aspects B1 to B6 or Intermediate B, E is R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R 5 A compound that is NS(O)2-. [Aspect B11] In any of Aspects B1 to B6 or Intermediate B, E is R 3 R 5 A compound that is NC(O)-. [Aspect B12] A compound in any one of Aspects B1 to B6 or Intermediate B, wherein E is a benzyl group or a (C3-C6 cycloalkyl)methyl group.

[0021] Examples of intermediate C include the following compounds:

[0022] [Aspect C1] A compound in which n is 0 in Intermediate C. [Aspect C2] A compound in either Aspect C1 or Intermediate C, wherein E is a methyl group substituted with one or more substituents selected from Group A, or a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from Group A. [Aspect C3] A compound in either aspect C1 or intermediate C, wherein E is a methyl group substituted with one or more substituents selected from group A. [Aspect C4] A compound in either aspect C1 or intermediate C, wherein E is a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from group A. [Embodiment C5] In either embodiment C1 or intermediate C, E is R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R 5 A compound that is NS(O)2-. [Aspect C6] In either aspect C1 or intermediate C, E is R 3 R 5 A compound that is NC(O)-. [Embodiment C7] A compound in either embodiment C1 or intermediate C, wherein E is a benzyl group or a (C3-C6 cycloalkyl)methyl group.

[0023] Examples of intermediate D include the following compounds:

[0024] [Aspect D1] A compound in which n is 0 in intermediate D. [Aspect D2] In aspect D1, R 1 is a methyl group or a chlorine atom. [Aspect D3] In aspect D1, R 1 is a methyl group. [Embodiment D4] The compound in embodiment D1, wherein L is an oxygen atom. [Embodiment D5] The compound in embodiment D2, wherein L is an oxygen atom. [Embodiment D6] The compound in embodiment D3, wherein L is an oxygen atom. [Aspect D7] In aspect D1, R 1 A compound in which the atom is chlorine. [Embodiment D8] The compound in embodiment D7, wherein L is an oxygen atom. [Embodiment D9] The compound in embodiment D1, wherein L is CH2. [Embodiment D10] The compound in embodiment D2, wherein L is CH2. [Embodiment D11] The compound in embodiment D3, wherein L is CH2. [Embodiment D12] The compound in embodiment D7, wherein L is CH2.

[0025] Next, the method for producing the compound of the present invention will be described.

[0026] Manufacturing method A The compound represented by formula (I-E1) (hereinafter referred to as compound (I-E1)) can be produced by reacting intermediate A represented by formula (II) with a compound represented by formula (R1) (hereinafter referred to as compound (R1)) in the presence of phosphines and azodiesters. [ka] [In the formula, E 1 represents a methyl group substituted with one or more substituents selected from group A, or a C2-C10 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, 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 hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and dimethoxyethane (hereinafter referred to as ethers); halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); amides such as dimethylformamide (hereinafter referred to as DMF) and N-methylpyrrolidone (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles), and mixtures of two or more of these. Examples of phosphines include triphenylphosphine and trimethylphosphine. Azodiesters include, for example, diethyl azodicarboxylate, diisopropyl azodicarboxylate, and bis(2-methoxyethyl) azodicarboxylate. In the reaction, the compound (R1) is usually used in a ratio of 1 to 10 moles, the phosphine is usually used in a ratio of 1 to 10 moles, and the azodiester is usually used in a ratio of 1 to 10 moles, relative to 1 mole of intermediate A. The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (I-E1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (R1) is known or can be produced according to a known method.

[0027] Manufacturing method B Compound (I-E1) can also be produced by reacting intermediate A represented by formula (II) with a compound represented by formula (R2) (hereinafter referred to as compound (R2)) in the presence of a base. [ka] [In the formula, X 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyl group, or a p-toluenesulfonyl group, and other symbols have the same meanings as above. The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof. Examples of bases include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate (hereinafter referred to as alkali metal bicarbonates); sodium hydride and tripotassium phosphate. In the reaction, the compound (R2) is usually used in a proportion of 1 to 10 moles, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of intermediate A. The reaction temperature is usually within the range of −20 to 150° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (I-E1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (R2) is known or can be produced according to a known method.

[0028] Manufacturing method C The compound represented by formula (I-E2) (hereinafter referred to as compound (I-E2)) can be produced by reacting intermediate A represented by formula (II) with a compound represented by formula (R3) (hereinafter referred to as compound (R3)) in the presence of a base. [ka] [In the formula, E 2 is R 6 C(O)-, R 4 OC(O)-, R 3 R 5 NC(O)-, R 3 R 5 NC(S)-, R 4 S(O)2- or R 3 R 5 NS(O)2-, and other symbols have the same meanings as above. The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof. Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride, and tripotassium phosphate. In the reaction, the compound (R3) is usually used in a proportion of 1 to 10 moles, and the base is usually used in a proportion of 1 to 10 moles, relative to 1 mole of intermediate A. The reaction temperature is usually within the range of −78 to 100° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (I-E2) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (R3) is known or can be produced according to a known method.

[0029] Manufacturing method D The compound represented by formula (I-E3) (hereinafter referred to as compound (I-E3)) can be produced by reacting intermediate A represented by formula (II) with triphosgene in the presence of a base, followed by reaction with a compound represented by formula (R4) (hereinafter referred to as compound (R4)). This reaction can be carried out in one pot. [ka] [In the formula, E 3 is R 4 O- or R 3 R 5 N-, and other symbols have the same meanings as above. The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof. Examples of the base include organic bases. In the reaction, triphosgene is usually used in a proportion of 0.3 to 3 moles, a base is usually used in a proportion of 1 to 10 moles, and compound (R4) is usually used in a proportion of 1 to 10 moles, relative to 1 mole of intermediate A. The reaction temperature of the reaction of intermediate A with triphosgene is usually within the range of -78 to 100°C, and the reaction time is usually within the range of 0.1 to 48 hours. The subsequent reaction temperature with compound (R4) is usually within the range of -78 to 100°C, and the reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (I-E3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (R4) is known or can be produced according to a known method.

[0030] Manufacturing method E The compound N of the present invention can be produced by reacting the intermediate B represented by formula (III) with iodomethane in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof. Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride, and mixtures thereof. In the reaction, iodomethane is usually used in a proportion of 1 to 10 moles and a base is usually used in a proportion of 1 to 20 moles relative to 1 mole of intermediate B. The reaction temperature is usually within the range of −20 to 100° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, the compound N of the present invention can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

[0031] Manufacturing method F Compound (I-E1) can be produced by reacting intermediate D represented by formula (VI) with compound (R1) in the presence of a palladium catalyst. [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, or a mixture of two or more thereof. Examples of palladium catalysts used in the reaction include palladium(II) acetate, {1,1'-bis(diphenylphosphino)ferrocene}dichloropalladium(II), XPhos Pd G3, BrettPhos Pd G3, tBuBrettPhos Pd G3, XantPhos Pd G3, and RockPhos Pd G3. If necessary, a ligand, a base or an additive may be added to the reaction. Examples of the ligand used in the reaction include 2-(di-t-butylphosphino)-1,1′-binaphthyl, BrettPhos, tBuBrettPhos, RockPhos, AdBrettPhos, tBuXPhos, and 5-(di-t-butylphosphino)-1′,3′,5′-triphenyl-1′H-[1,4′]bipyrazole. When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mole per mole of intermediate D. Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkali metal alkoxides such as potassium t-butoxide and sodium t-butoxide; and tripotassium phosphate. When a base is used in the reaction, the base is usually used in a proportion of 1 to 10 moles per mole of intermediate D. Examples of additives used in the reaction include sodium iodide and potassium iodide. When an additive is used in the reaction, the additive is usually used in a ratio of 0.1 to 10 moles per mole of intermediate D. In the reaction, the compound (R1) is usually used in a proportion of 1 to 10 moles, and the palladium catalyst is usually used in a proportion of 0.01 to 1 mole, relative to 1 mole of intermediate D. The reaction temperature is usually within the range of 0 to 150° C. The reaction time is usually within the range of 0.1 to 120 hours. After the reaction is complete, compound (I-E1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (R1) is known or can be produced according to a known method.

[0032] Manufacturing method G The N-oxide of the compound N of the present invention can be produced by reacting the compound N of the present invention with an oxidizing agent. The reaction can be carried out, for example, according to the method described in U.S. Patent Application Publication No. 2018 / 0009778 or WO 2016 / 121970.

[0033] Reference manufacturing method A Intermediate A represented by formula (II) can be produced by reacting a compound represented by formula (II-A) (hereinafter referred to as compound (II-A)) with bis(pinacolato)diboron in the presence of a base and a palladium catalyst to obtain a compound represented by formula (II-B) (hereinafter referred to as compound (II-B)), and then oxidizing compound (II-B). [ka] [In the formula, X 2 represents a bromine atom, an iodine atom or a trifluoromethanesulfonyl group, and the other symbols have the same meanings as above.

[0034] First, a method for producing compound (II-B) from compound (II-A) will be described. The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, sulfoxides (hereinafter referred to as sulfoxides) such as dimethyl sulfoxide (hereinafter referred to as DMSO), nitriles, and mixtures of two or more of these. Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogencarbonates, and tripotassium phosphate. The palladium catalyst includes, for example, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride. In the reaction, bis(pinacolato)diboron is usually used in a proportion of 1 to 5 moles, a base is usually used in a proportion of 1 to 5 moles, and a palladium catalyst is usually used in a proportion of 0.01 to 0.5 moles, relative to 1 mole of compound (II-A). The reaction temperature is usually within the range of 0 to 150°C, and the reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, compound (II-B) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

[0035] Next, a method for producing intermediate A from compound (II-B) will be described. The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols such as methanol, ethanol, propanol, and butanol (hereinafter referred to as alcohols), water, and mixtures thereof. Examples of the oxidizing agent used in the reaction include metachloroperbenzoic acid and aqueous hydrogen peroxide. When hydrogen peroxide water is used as the oxidizing agent, a base may be added as necessary. Bases include sodium hydroxide and potassium hydroxide. In the reaction, the oxidizing agent is usually used in a proportion of 1 to 5 moles per mole of compound (II-B). When a base is used in the reaction, the base is usually used in a proportion of 0.1 to 5 moles per mole of compound (II-B). The reaction temperature is usually within the range of −20 to 120° C., and the reaction time is usually within the range of 0.1 to 48 hours. After the reaction is completed, intermediate A can be isolated by adding water and a reducing agent such as sodium thiosulfate to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. Compound (II-A) is known or can be produced according to a known method.

[0036] Reference manufacturing method B Intermediate B represented by formula (III) can be produced by reacting a compound represented by formula (V) (hereinafter referred to as compound (V)) with methyl formate in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction is usually carried out in a solvent, such as hydrocarbons, ethers, halogenated hydrocarbons, amides, nitriles, and mixtures of two or more thereof. Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide; alkali metal amides such as sodium amide, lithium amide, lithium diisopropylamide, sodium hexamethyldisilazide and lithium hexamethyldisilazide; and mixtures thereof. In the reaction, methyl formate is usually used in a proportion of 1 to 100 moles and the base is usually used in a proportion of 1 to 10 moles per mole of compound (V). The reaction temperature is usually within the range of −20 to 80° C. The reaction time is usually within the range of 0.1 to 48 hours. After the reaction is complete, intermediate B can be isolated by adding an acidic aqueous solution such as dilute hydrochloric acid to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.

[0037] Reference manufacturing method C The compound represented by formula (V-E1) (hereinafter referred to as compound (V-E1)) can be produced by reacting a compound represented by formula (VA) (hereinafter referred to as compound (VA)) with compound (R1) in the presence of a phosphine and an azodiester. [ka] (wherein the symbols have the same meanings as defined above.) The reaction can be carried out according to Production Method A, except that compound (VA) is used in place of intermediate A. Compound (VA) is known or can be produced according to a known method.

[0038] Reference manufacturing method D The compound represented by formula (V-E2) (hereinafter referred to as compound (V-E2)) can be produced by reacting compound (VA) with compound (R3) in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction can be carried out according to Production Method C, except that compound (VA) is used in place of intermediate A.

[0039] Reference manufacturing method E Intermediate D can be produced by reacting a compound represented by formula (VI-A) (hereinafter referred to as compound (VI-A)) with iodomethane in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction can be carried out according to Production Method E, except that compound (VI-A) is used in place of intermediate B.

[0040] Reference manufacturing method F Compound (VI-A) can be produced by reacting a compound represented by formula (VI-B) (hereinafter referred to as compound (VI-B)) with methyl formate in the presence of a base. [ka] (wherein the symbols have the same meanings as defined above.) The reaction can be carried out according to Reference Production Method B, using compound (VI-B) instead of compound (V). Compound (VI-B) is known or can be produced according to a known method.

[0041] The compound of the present invention can be mixed or used in combination with one or more components (hereinafter referred to as the present components) selected from the group consisting of the following groups (a), (b), (c), and (d): The above-mentioned mixed or concomitant use means that the compound of the present invention and the present ingredient are used simultaneously, separately or with an interval between them. When the compound of the present invention and this ingredient are used simultaneously, the compound of the present invention and this ingredient may be contained in separate preparations or may be contained 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), and the compound of the present invention.

[0042] 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, glutamatergic 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 synthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complex I, II, The group consisting of inhibitors of genotypes III and IV, voltage-gated 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 are described in the IRAC mechanism-based classification.

[0043] 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 synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These are described in the FRAC classification based on the mechanism of action.

[0044] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0045] Group (d) is a group of repellent ingredients.

[0046] Examples of combinations of the present ingredient and the compound of the present invention are described below: For example, alanycarb + SX means a combination of alanycarb and SX. The abbreviation SX means any one of the compounds of the present invention selected from the compound group SX1 to SX80 described in the Examples. The present components described below are all known components and can be obtained from commercially available preparations or produced by known methods. When the present components are microorganisms, they can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).

[0047] Combination of the present component 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 + SX, coumaphos + SX, Cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cycloniliprole + SX,Cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + 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, dimpropyridazol + 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, Cassia nigricans extract + SX, Clitoria ternatea extract (extract of Clitoria ternatea) + SX, Symphytum officinale extract (extract of Symphytum officinale) + SX, Chenopodium ambrosioides extract (extracts or simulated blend of Chenopodium ambrosioides) + SX, Tansy extract (extract of Tanacetum vulgare) + SX, Urtica dioica extract (extract of Urtica dioica) + SX, Viscum album extract (extract of Viscum album) + SX, Famphur + SX, Fenamiphos + SX, Fenazaquin + SX, Fenbutatin oxide + SX, Fenitrothion + 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, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenprox + SX, flufenoxuron + SX, Flufiprole + SX, flumethrin + SX, flupyradifurone + SX, flupyrimin + 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, 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, 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, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, neem oil + 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, spinetoram + SX, spinosad + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX,Spirotetramat + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, 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, tioxazafen + SX, tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX, triflumezopyrim + SX, Triflumuron + SX, trimethacarb + SX,Tyclopyrazoflor + SX, vamidothion + SX, Quassia amara wood extract + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropanesulfinyl)propanamide (1477923-37-7) + 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-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoropropane-2-yl)phenyl]-3-{ethyl[(pyridin-4-yl)carbonyl]amino}-2-methoxybenzamide (1429513-53-0) + SX, N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoropropane-2-yl)phenyl]-3-[ethyl(4-cyanobenzoyl)amino]-2-methoxybenzamide (1609007-65-9) + SX, N-[2-bromo-6-(difluoromethoxy)-4-(1,1,1,2,3,3,3-heptafluoropropane-2-yl)phenyl]-3-{methyl[(pyridin-4-yl)carbonyl]amino}-2-methoxybenzamide (1630969-78-6) + SX, 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (885026-50-6) + SX, (1Z)-2-(4-tert-butylphenyl)-2-cyano-1-(1-ethyl-3-methyl-1H-pyrazol-5-yl)ethenyl 2,2-dimethylpropanoate (1253429-01-4) + SX, N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide + SX, BT crop protein Cry1Ab (BT crop protein Cry1Ab) + SX, BT crop protein Cry1Ac (BT crop protein Cry1Ac) + SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa) + SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX, BT crop protein Vip3A (BT crop protein Vip3A) + SX, BT crop protein Cry3A (BT crop protein Cry3A) + SX, BT crop protein Cry3Ab (BT crop protein Cry3Ab) + SX BT crop protein Cry3Bb (BT crop protein Cry3Bb) + SX, BT crop protein Cry34Ab1 / Cry35Ab1 (BT crop protein Cry34Ab1 / Cry35Ab1) + SX,Adoxophyes orana granulosis virus strain BV-0001 + SX, Anticarsia gemmatalis mNPV + 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 SX, Helicoverpa armigera NPV strain BV-0003 + SX, Helicoverpa zea NPV + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX, Mamestra configurata NPV + SX, Neodiprion abietis NPV + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer nuclear polyhedrosis virus (NPV) + SX, Nosema locustae nuclear polyhedrosis virus (NPV) + SX, Orgyia pseudotsugata nuclear polyhedrosis virus (NPV) + SX,Pieris rapae GV + SX, Plodia interpunctella GV + SX, Spodoptera exigua mNPV) + SX, Spodoptera littoralis mNPV + SX, Spodoptera litura NPV + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 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 Serotype strain H-7 + SX,Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG234 + 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, Dactylaria 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 thoynei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, 2-chloro-4-fluoro-5-{[5-(trifluoromethylthio)pentyl]oxy}phenyl 2,2,2-trifluoroethyl sulfoxide (1472050-04-6) + SX, 4-chloro-5-[2,2-difluoro-2-(3,4,5-trifluorophenyl)ethoxy]-2-methylphenyl 2,2,2-trifluoroethyl sulfoxide (1632218-00-8) + SX, 4-fluoro-5-[2,2-difluoro-2-(3,4,5-trifluorophenyl)ethoxy]-2-methylphenyl 2,2,2-trifluoroethyl sulfoxide (1632217-98-1) + SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium-5-olate (2249718-27-0) + 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, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one (907187-07-9) + SX, 3-(4'-fluoro-2,4-dimethyl[1,1'-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one (1031385-91-7) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, ニコフルプロール(nicofluprole) + SX, 1,4-dimethyl-2-[2-(3-pyridinyl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX。,

[0048] Combination of the present component 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, 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, tea tree extract (Melaleuca alternifolia) + SX, Japanese knotweed extract (Reynoutria sachalinensis) + SX, lupine seedling cotyledon extract (BLAD) + SX, garlic extract (Allium sativum) + SX, horsetail extract (Equisetum arvense) + SX, Nasturtium extract (Tropaeolum majus extract) + 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 (fentin acetate) + SX, triphenyltin chloride (fentin chloride) + SX, triphenyltin hydroxide (fentin hydroxide) + SX,Ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, fludioxonil + SX, flufenoxystrobin + SX, fluindapyr + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluquinconazole + SX, Flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetylaluminium + 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, isofleucine + SX, isofleucine + SX, isofleucine + 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, metconazole + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, Methyltetraprole + SX, mineral oils + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX,Octilinone + 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 + 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, mustard powder + SX, zinc thiazole + SX, zineb + ​​SX, ziram + SX, zoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-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-choro-4-(2-fluorophenoxy)-2-methylphenyl)-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-choro-4-(2-fluorophenoxy)-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-m, ethyl-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, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one (1616664-98-2) + 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, 4-({6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]pyridin-3-yl}oxy)benzonitrile (2046300-61-0) + 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), 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, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens (Aveo(trademark) 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, フルベネテラム(flubeneteram) + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, (2S,3S)-3-(2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate (2376210-00-1) + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate (2376209-13-9) + SX, (2S,3S)-3-(2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376210-02-3) + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376209-40-2) + SX, (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376209-15-1) + SX. ,

[0049] Combination of the present component of the above group (c) 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, 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 Decane-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 hydrazide + SX, mefluidide + SX, mepiquat chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexandione calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintophen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, streptomycin + 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]-1-propanol + 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. ,

[0050] Combination of the present component of the above group (d) with the compound of the present invention: Anthraquinone + SX, deet + SX, icaridin + SX.

[0051] 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.

[0052] The compound of the present invention is effective against pests, such as plant pathogenic microorganisms, harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks.

[0053] The compound of the present invention can control plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, Phytomyxea, and bacteria. Examples of fungi include Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specific examples include the following: The scientific name of the plant pathogenic microorganism that causes each disease is shown in parentheses.

[0054] Rice diseases: blast (Pyricularia oryzae), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellow dwarf disease (Sclerophthora macrospora), rhizobacterial blast and panicle blight (Epicoccum nigrum), seedling damping-off (Trichoderma viride, Rhizopus oryzae); Wheat diseases: Powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), pink snow blight (Microdochium nivale, Microdochium majus), snow blight (Typhula incarnata, Typhula ishikariensis), naked smut (Ustilago tritici), smut (Tilletia caries, Tilletia controversa), eyespot (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), leaf spot (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), seedling damping off caused by Rhizoctonia fungi (Rhizoctonia solani), damping off (Gaeumannomyces graminis), rice blast (Pyricularia graminis-tritici); Barley diseases: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), small rust (Puccinia hordei), naked smut (Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf spot (Pyrenophora graminea), Ramularia leaf spot (Ramularia collo-cygni), seedling damping-off (Rhizoctonia solani); Corn diseases: rust (Puccinia sorghi), southern rust (Puccinia polysora), sooty leaf blight (Setosphaeria turcica), tropical rust (Physopella zeae), southern leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), ear smut (Ustilago maydis), Physoderma maydis; Cotton diseases: Anthracnose (Colletotrichum gossypii), White mold (Ramularia areola), Black spot (Alternaria macrospora, Alternaria gossypii), Black root rot (Thielaviopsis basicola); Coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); Diseases of rapeseed: Sclerotinia sclerotiorum, Alternaria brassicae, Phoma lingam, light leaf spot (Pyrenopeziza brassicae); Sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); Sunflower diseases: rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); Citrus diseases: black spot (Diaporthe citri), common scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger; Apple diseases: Monilinia blight (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), scab (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring spot (Botryosphaeria berengeriana), late blight (Phytophtora cactorum), red scab (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae); Pear diseases: black scab (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), red scab (Gymnosporangium haraeanum); Peach diseases: brown rot (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis rot (Phomopsis sp.), leaf curl (Taphrina deformans); Grape diseases: black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola); Persimmon diseases: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf fall (Cercospora kaki, Mycosphaerella nawae); Fig diseases: Rust (Phakopsora nishidana); Cucurbit diseases: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), vine wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora capsici), seedling damping-off (Pythium sp.); Tomato diseases: ring blight (Alternaria solani), leaf mold (Cladosporium fulvum), sooty mold (Pseudocercospora fuligena), late blight (Phytophthora infestans), powdery mildew (Leveillula taurica); Eggplant diseases: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); Diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida); Diseases of leeks: rust (Puccinia allii); Soybean diseases: purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia sclerotiorum, powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe / Phomopsis complex (Diaporthe longicolla); Diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani); Peanut diseases: black leaf spot (Cercospora personata), brown spot (Cercospora arachidicola), white blight (Sclerotium rolfsii), black root rot (Calonectria ilicicola); Pea diseases: powdery mildew (Erysiphe pisi), root rot (Fusarium solani); Potato diseases: summer blight (Alternaria solani), late blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. sp. subterranea), verticillium wilt (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), canker (Synchytrium endobioticum); Strawberry diseases: Powdery mildew (Sphaerotheca humuli); Tea diseases: Net blight (Exobasidium reticulatum), White scab (Elsinoe leucospila), Ring spot (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis); Tobacco diseases: red star (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae); Diseases of sugar beet: Cercospora beticola, leaf rot (Thanaphorus cucumeris), root rot (Thanaphorus cucumeris), black root disease (Aphanomyces cochlioides), rust (Uromyces betae); Rose diseases: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Chrysanthemum diseases: brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana); Onion diseases: white spotted leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotial rot (Botrytis squamosa); Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia rot (Sclerotinia sclerotiorum), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum); Radish diseases: black spot (Alternaria brassicicola); Lawngrass diseases: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), red blight (Pythium aphanidermatum); Banana diseases: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola); Lentil diseases: Ascochyta disease (Ascochyta lentis); Chickpea diseases: Ascochyta disease (Ascochyta rabiei); Diseases of bell pepper: anthracnose (Colletotrichum scovillei); Mango diseases: Anthracnose (Colletotrichum acutatum); Fruit tree diseases: White root rot (Rosellinia necatrix), Purple root rot (Helicobasidium mompa); Post-harvest diseases of apples, pears, and other fruits: Mucor rot (Mucor piriformis); Seed diseases or early growth diseases caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc.; Viral diseases: big vein disease of lettuce transmitted by Olpidium brassicae, viral diseases of various crops transmitted by Polymyxa species (e.g., Polymyxa betae and Polymyxa graminis); Diseases caused by bacteria: rice seedling blight (Burkholderia plantarii), cucumber spot (Pseudomonas syringae pv. Lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces scabiei), corn Goss's wilt (Clavibacter michiganensis), Pierce's disease (Xylella fastidiosa) of grapes, olives, peaches, etc., and crown gall (Agrobacterium tumefaciens) of Rosaceae plants such as apples, peaches, and cherries.

[0055] Examples of harmful arthropods, harmful nematodes, and harmful mollusks include the following:

[0056] 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 and other Delphacidae; Green rice leafhopper (Nephotettix cincticeps), Taiwanese green rice leafhopper (Nephotettix virescens), Black-striped green rice leafhopper (Nephotettix nigropictus), Lightning leafhopper (Recilia dorsalis), Tea green leafhopper (Empoasca onukii), Potato leafhopper (Empoasca Cicadellidae, such as the corn leafhopper (Dalbulus fabae), the white 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 boll aphid (Ceratovacuna lanigera), apple aphid (Eriosoma lanigerum), English grain aphid (Sitobion avenae), and other aphids (Aphididae); grapevine 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); the rice black bug (Scotinophara lurida), the black paddy bug (Scotinophara coarctata), the green grass bug (Nezara antennata), the spiny spotted bug (Eysarcoris aeneus), the large spiny spotted bug (Eysarcoris lewisi), the white spotted bug (Eysarcoris ventralis), the purple spotted bug (Eysarcoris annamita), the brown marmorated stink bug (Halyomorpha halys), and the southern green stink bug (Nezara Pentatomidae (Pentatomidae) such as the brown stink bug (Euschistus heros), the red-banded stink bug (Piezodorus guildinii), the red-banded stink bug (Oebalus pugnax), and the Dichelops melacanthus; Cydnidae (Scaptocoris castanea) and the like; Alydidae (Riptortus clavatus), the spider stink bug (Leptocorisa chinensis), and the narrow-legged stink bug (Leptocorisa acuta); Coreidae (Celetus punctiger, Leptoglossus australis), and the long-legged stink bug (Cavelerius Lygaeidae, including the common long-horned bug (Togo hemipterus), the American long-horned bug (Blissus leucopterus), and others;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 whitefly (Pealius euryae); Diaspididae, such as Aonidiella aurantii, Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, and Unaspis citri; Coccidae, such as Ceroplastes rubens; Margarodidae, such as Icerya purchasi and 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 pear earworm (Stephanitis nashi), and the azalea earworm (Stephanitis pyrioides); Cimicidae, such as the bedbug (Cimex lectularius) and the net bug (Cimex hemipterus); Cicadidae, such as the Brazilian assassin bug (Triatoma infestans), the giant assassin bug (Triatoma rubrofasciata), and the Venezuelan assassin bug (Rhodonius Reduviidae, such as Triatomine bugs (e.g., Triatomine spp.), Triatomine spp., ...

[0057] 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), armyworm (Spodoptera mauritia), two-banded cutworm (Naranga aenescens), Spodoptera frugiperda, African armyworm (Spodoptera exempta), Spodoptera cosmioides, semi-tropical armyworm (Spodoptera eridania), cutworm moth (Agrotis ipsilon), silver ringworm (Autographa nigrisigna), rice yellow looper (Plusia festucae), soybean looper (Chrysodeixis includens), Trichoplusia 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), cotton leafworm (Alabama argillacea), and 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), sugar candy moth (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), citrus fruit borer (Citripestis sagittiferella), European grape wine moth (Lobesia Tortricidae (Tortricidae) such as Caloptilia theivora and Phyllonorycter ringoniella; Gracilariae (Gracillariidae) such as Caloptilia theivora and Phyllonorycter ringoniella; Carposinidae (Carposinidae) such as Carposina sasakii; Lyonetiidae (Lyonetiidae) such as Leucoptera coffeella, Lyonetia clerkella, and Lyonetia prunifoliella; Lymantriidae (Lymantria spp.) such as Lymantria dispar and Euproctis spp. such as Euproctis pseudoconspersa; Plutellidae (Plutellidae) such as Plutella xylostella;Gelechiidae (Gelechiidae) such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Tuta absoluta; Arctiidae (Arctiidae) such as Hyphantria cunea; Castniidae (Castniidae) such as Telchin licus; Cossidae (Cossus insularis); Geometridae (Geometridae) such as Ascotis selenaria; Limacodidae (Limaculidae) such as Parasa lepida; and Stathmopoda Stathmopodidae such as Acherontia masinissa; Sphingidae such as Acherontia lachesis; Sesiidae such as Nokona feralis, Synanthedon hector, and Synanthedon tenuis; Hesperiidae such as Parnara guttata; Tineidae such as Tinea translucens and Tineola bisselliella;

[0058] 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.

[0059] 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 cucurbitae (such as Bactrocera cucurbitae) and Bactrocera citri (such as Bactrocera cucurbitae). Tephritidae, such as Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, and Rhacochlaena japonica; Ephydridae, such as Hydrellia griseola, Hydrellia philippina, and Hydrellia sasakii; Drosophila suzukii, Drosophila melanogaster; Drosophilidae, such as Drosophila melanogaster; Phoridae, such as Megaselia spiracularis; Psychodidae, such as Clogmia albipunctata; Sciaridae, such as Bradysia difformis;Cecidomyiidae (Cicedomyiidae) 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 (Sandflies); Tipulidae (Crane flies) such as Tipula aino, Common crane fly (Tipula oleracea), and European crane fly (Tipula paludosa); Culex pipiens pallens and Culex pipiens pallens tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles Culicidae (such as Prosimulium yezoensis and Simulium ornatum); Tabanidae (such as Tabanus trigonus);Muscidae, such as the house fly (Musca domestica), the giant house fly (Muscina stabulans), the stable fly (Stomoxys calcitrans), and the horn fly (Haematobia irritans); Calliphoridae; Sarcophagidae; Chironomidae, such as the giant midge (Chironomus plumosus), the Japanese midge (Chironomus yoshimatsui), and the gray midge (Glyptotendipes tokunagai); Fannidae;

[0060] Coleoptera: Diabrotica spp., for example, the western corn rootworm (Diabrotica virgifera virgifera), the southern corn rootworm (Diabrotica undecimpunctata howardi), the northern corn rootworm (Diabrotica barberi), and the Mexican corn rootworm (Diabrotica virgifera zeae), bean leaf beetles (Cerotoma trifurcata) such as the banded cucumber beetle (Diabrotica balteata) and the cucumber beetle (Diabrotica speciosa), the spotted neck leaf beetle (Oulema melanopus), the cucumber leaf beetle (Aulacophora femoralis), the striped flea beetle (Phyllotreta striolata), the cabbage leaf beetle (Phyllotreta cruciferae), and the western black leaf beetle (Phyllotreta Chrysomelidae, such as the 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), and tobacco flea beetle (Epitrix hirtipennis); seed corn beetle (Stenolophus lecontei), Slender Seed Corn Beetle (Clivina impressifrons), and other ground beetles (Carabidae);Scarabaeidae beetles such as the cuprea beetle (Anomala cuprea), the rufocuprea beetle (Anomala rufocuprea), the albopilosa beetle (Anomala albopilosa), the Japanese beetle (Popillia japonica), the long-legged scarab beetle (Heptophylla picea), the European chafer (Rhizotrogus majalis), the black marmorated beetle (Tomarus gibbosus), the black scarab beetle (Holotrichia spp.), the June beetle (Phyllophaga crinita), and other Phyllophaga spp., and Diloboderus spp. such as Diloboderus abderus; Anthriibidae beetles such as the boll weevil (Araecerus coffeae); The family Aponidae includes the sweet potato weevil (Cylas formicarius); the family Bruchidae includes the Brazilian bean weevil (Zabrotes subfasciatus); the family Scolytidae includes the pine bark beetle (Tomicus piniperda) and the coffee berry borer (Hypothenemus hampei);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 included in the Curculionidae family; the Tenebrionidae (Tribolium castaneum, Tribolium confusum, Alphitobius diaperinus, and the like); the Coccinellidae (Coccinellidae) (Epilachna vigintioctopunctata, and the like); the Flat-headed Beetle (Lyctus brunneus), the Long-horned Bostrychidea (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 earwig beetle (Paederus fuscipes); the small-leaved earwig beetle (Anthrenus verbasci) and the white-striped earwig beetle (Dermestes Dermestidae, such as Trogoderma granarium (Trogoderma maculates) and Lasioderma serricorne (tobacco beetle), Anobiidae, such as Stegobium paniceum (Anobiidae); Laemophloeidae, such as Cryptolestes ferrugineus (Laemophloeidae); Silvanidae, such as Oryzaephilus surinamensis (Sawtooth beetle), and Nitidulidae, such as Brassicogethes aeneus (Blossom beetle);

[0061] 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 field 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).

[0062] 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, Argentine ant, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole Camponotus spp. such as Camponotus noda, Pheidole megacephala, Camponotus japonicus, and Camponotus obscuripes; Pogonomyrmex spp. such as Pogonomyrmex occidentalis; Wasmania spp. such as Wasmania auropunctata; and Formicidae such as Anoplolepis gracilipes; Vespa mandarinia, Vespa simillima, Vespa analis, and Vespa Vespidae, such as the Japanese paper wasp (Polistes velutina) and the Japanese paper wasp (Polistes jokahamae); Siricidae, such as the Japanese wood wasp (Urocerus gigas); and Bethylidae.

[0063] Order 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.

[0064] Order Siphonaptera: Pulex spp. such as the human flea (Pulex irritans), Ctenocephalides spp. such as the cat flea (Ctenocephalides felis) and the dog flea (Ctenocephalides canis), Xenopsylla spp. such as the rat flea (Xenopsylla cheopis), Tunga spp. such as the sand flea (Tunga penetrans), Echidnophaga spp. such as the chicken flea (Echidnophaga gallinacea), and Nosopsyllus spp. such as the European rat flea (Nosopsyllus fasciatus).

[0065] Psocodae: Pediculus spp. such as head louse (Pediculus humanus capitis); Phtirus spp. such as pubic louse (Pthirus pubis); Haematopinus spp. such as cow louse (Haematopinus eurysternus) and pig louse (Haematopinus suis); Bovicola spp. such as cow louse (Bovicola bovis), sheep louse (Bovicola ovis), and Bovicola breviceps; Damalinia spp. such as Damalinia forficula; Linognathus vituli, sheep trunk louse (Linognathus Linognathus spp. such as the woolly cow louse (Solenopotes capillatus); Menopon spp. such as the chicken louse (Menopon gallinae); Cummingsia spp.; Trinoton spp.; Trichodectes spp. such as the dog louse (Trichodectes canis); Felicola spp. such as the cat louse (Felicola subrostratus); Menacanthus spp. such as the chicken louse (Menacanthus stramineus); Werneckiella spp.; Trogium Trogiidae (Psociidae) such as Liposcelis corrodens, Liposcelis bostrychophila, Liposcelis pearmani, Liposcelis entomophila, and other Liposcelididae.

[0066] Thysanura: Family Lepismatidae, including the Japanese silverfish (Ctenolepisma villosa) and the European silverfish (Lepisma saccharina).

[0067] Acari: Tetranychidae, such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, and Oligonychus spp.; Aculops pelekassi, Aculops citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, and Aculus 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.; Sarcoptidae, such as Notoedres cati, Notoedres muris, and Sarcoptes scabiei; Listrophorus Listrophoridae such as Dermanyssus gibbus; Dermanyssidae such as Dermanyssus gallinae; Macronyssidae such as Ornithonyssus sylviarum and Ornithonyssus bacoti; Varroidae such as Varroa jacobsoni; Demodex canis and Demodex cati; Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium scutellaris. Trombiculidae, such as scutellare;

[0068] Araneae: Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii. Polydesmida: Paradoxosomatidae, including Oxidus gracilis and Nedyopus tambanus. Isopoda: Armadillidiidae, including 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 little apple snail (Austropeplea ollula).

[0069] 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), and potato cyst nematode (Globodera Heteroderidae such as Globodera pallida (potato white cyst nematode) and Rotylenchulus reniformis (Hoplolaimidae) such as Nothotylenchus acris (strawberry root nematode) and Ditylenchus dipsaci (sea nematode) such as Anguinidae; Tylenchulidae such as Tylenchulus semipenetrans (citrus root nematode) such as Xiphinema index (grape nematode); Trichodoridae; Parasitaphelenchidae such as Bursaphelenchus xylophilus (pine wood nematode).

[0070] 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 chemical sensitivity or have developed chemical resistance to insecticides, acaricides, molluscicides, and nematodes.

[0071] The pest control method 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 pest and / or to the habitat of the pest (plants, soil, inside a house, animals, etc.). Examples of the pest control method of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, and seed treatment.

[0072] The compound of the present invention or Composition A is usually mixed with an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier, and, if necessary, surfactants and other formulation adjuvants are added to formulate it into an emulsion, oil, dust, granule, wettable powder, water dispersible granule, flowable, dry flowable, microcapsule, aerosol, poison bait, resin formulation, paste formulation, foam, carbon dioxide formulation, etc. These formulations may also be processed into mosquito coils, electric mosquito mats, liquid mosquito repellent formulations, smoke formulations, fumigants, and sheet formulations for use. These formulations typically contain the compound of the present invention or Composition A in a weight ratio of 0.01 to 95.

[0073] Examples of solid carriers used in formulation include fine powders and granules of clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymer, etc.).

[0074] Examples of liquid carriers include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, diesel, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, acetone, methyl methyl ketone, methyl methyl naphthalene, etc.), and the like. Examples of suitable solvents include diisobutyl dipicate, propylene glycol monomethyl ether acetate, etc., nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, 1,4-dioxane, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol, etc.), amides (DMF, N,N-dimethylacetamide, etc.), sulfoxides (DMSO, etc.), propylene carbonate, and vegetable oils (soybean oil, cottonseed oil, etc.).

[0075] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.

[0076] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, and polyethylene glycol fatty acid esters, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates.

[0077] Other formulation adjuvants include adhesives, dispersants, colorants, and stabilizers, such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol). Specifically, 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).

[0078] Examples of the substrate for the resin preparation include vinyl chloride polymers and polyurethanes, and these substrates may contain, as needed, plasticizers such as phthalate esters (dimethyl phthalate, dioctyl phthalate, etc.), adipic acid esters, and stearic acid. Resin preparations are obtained by kneading compounds into the substrate using a conventional kneading device and then molding the mixture by injection molding, extrusion molding, press molding, or the like. If necessary, the mixture can be further processed, for example, through molding and cutting processes, into resin preparations in the form of plates, films, tapes, nets, strings, or the like. These resin preparations are processed into, for example, animal collars, animal ear tags, sheet preparations, attractants, and gardening supports. Examples of base materials for poison bait include grain flour, vegetable oil, sugar, and crystalline cellulose, and, if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, agents to prevent accidental ingestion by children and pets such as chili pepper powder, and pest-attracting flavors such as cheese flavoring, onion flavoring, and peanut oil may also be added.

[0079] 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.

[0080] Vegetative reproductive organs refer to plant roots, stems, leaves, and other parts that have the ability to 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 are a collective term for bulbs, corms, tubers, rhizomes, stem fragments, rhizophores, or tuberous roots. Potato cultivation begins by planting the tubers in soil, and the tubers used are generally called seed potatoes.

[0081] Examples of methods 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 the soil before or after planting a plant, a method of applying an effective amount of the compound of the present invention or composition A to the rhizosphere of a crop to be protected from damage such as feeding by harmful arthropods, and a method of systemically translocating an effective amount of the compound of the present invention or composition A from the roots or the like into the interior of the plant body to control harmful arthropods that feed on plants. More specifically, for example, planting hole treatment (planting hole spraying, planting hole treatment soil incorporation), plant base treatment (plant base spraying, plant base soil incorporation, plant base irrigation, plant base treatment in the latter half of the seedling raising period), planting furrow treatment (planting furrow spraying, planting furrow soil incorporation), row treatment (row spraying, row soil incorporation, row spraying during the growing period), row treatment at sowing (row spraying at sowing, row soil incorporation at sowing), overall treatment (overall soil spraying, overall soil incorporation), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spray treatments (granular foliar spray during the growing period, spraying under the crown or around the main trunk, soil surface spraying, soil surface incorporation, seeding hole spraying, furrow surface spraying, inter-row spraying), 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 with chemicals), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding with chemicals), seedbed treatments (seedling bed spraying, seedbed 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 (mixing culture soil, plowing in, mixing topsoil, mixing soil where rain falls, planting position treatment, spraying granular inflorescences, mixing paste fertilizer).

[0082] 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 mist form, smear treatments in which seeds or vegetative reproductive organs are coated with the compound of the present invention or composition A, immersion treatments in which seeds are immersed in a solution of the compound of the present invention or composition A for a certain period of time, and methods in which seeds or vegetative reproductive organs are coated with a carrier containing the compound of the present invention or composition A (film coating treatment, pellet coating treatment, etc.). The vegetative reproductive organs mentioned above particularly include seed potatoes. When applying Composition A to seeds or vegetative reproductive organs, the seeds or vegetative reproductive organs can be treated with a single formulation of Composition A, or the seeds or vegetative reproductive organs can be treated with multiple different formulations of Composition A in separate applications. Examples of methods of treating with multiple different formulations of Composition A in separate applications include a method of treating 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 with a formulation containing 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 this ingredient other than the ingredient that has already been treated. In the present invention, the seeds or vegetative reproductive organs carrying the compound of the present invention or composition A refer to seeds or vegetative reproductive organs in a state in which the compound of the present invention or composition A is attached to the surface of the seeds or vegetative reproductive organs. 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 thereto before or after the compound of the present invention or composition A is attached to the seeds or vegetative reproductive organs. When composition A is attached to the surface of a seed or vegetative reproductive organ in the form of a layer, the layer may consist of one or more layers. When the composition 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.

[0083] When the compound of the present invention or composition A is used for controlling pests in the agricultural field, the application rate 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.

[0084] Alternatively, the resin preparation can be processed into a sheet or string shape and wrapped around the crop, stretched around the crop, or spread on the soil around the base of the plant.

[0085] When the compound of the present invention or composition A is used to control harmful arthropods living in houses, the application rate is 1 / 2 m / day for surface treatment. 2 The amount of the compound of the present invention per 1 m2 of treatment space is usually 0.01 to 1000 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 is 0.1 to 10,000 ppm, whereas oil solutions, aerosols, fumigants, poison baits and the like are applied as is.

[0086] Furthermore, 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.

[0087] Corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, Solanaceae vegetables (eggplant, tomato, bell pepper, chili pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae 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 (horseshoe, etc.). vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, taro, pome fruits (apples, European pears, Japanese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (unshu mandarins, oranges, lemons, limes, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, olives, loquats, bananas, coffee, dates, coconuts, tea, mulberry, ornamental plants, forest plants, lawn grass, pasture grass.

[0088] The above plants also include genetically modified crops. [Example]

[0089] The present invention will be explained in more detail below by showing Production Examples, Reference Production Examples, Formulation Examples and Test Examples, but the present invention is not limited to these examples.

[0090] In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, Pen represents a pentyl group, i-Pr represents an isopropyl group, i-Bu represents an isobutyl group, c-Pr represents a cyclopropyl group, c-Bu represents a cyclobutyl group, c-Pen represents a cyclopentyl group, c-Hex represents a cyclohexyl group, and Ph represents a phenyl group.

[0091] First, examples of the preparation of the compounds of the present invention will be shown.

[0092] 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 [MH] - and retention time (hereinafter referred to as RT). The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.

[0093] [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: 254nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0mL / min Pump: LC-20AD (Shimadzu Corporation) 2 units (high pressure gradient) Gradient conditions: The solution is delivered at the concentration gradient shown in [Table LC1].

[0094] [Table 1]

[0095] [MS conditions] Detector: LCMS-2020 (Shimadzu Corporation) Ionization method: DUIS

[0096] Reference manufacturing example 1 A mixture of 20.0 g of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate (prepared by the method described in WO 2001 / 000562), 20.2 g of bis(pinacolato)diboron, 2.43 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, 19.5 g of potassium acetate, and 250 mL of DMSO was stirred at 80°C for 10 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 11.8 g of Intermediate 1 represented by the following formula: [ka] Intermediate 1: 1 H-NMR (CDCl3) δ: 7.37 (1H, d), 7.32 (1H, s), 7.16 (1H, d), 7.10 (1H, s), 3.87 (3H, s), 3.69 (3H, s), 2.37 (3H, s), 1.31 (12H, s).

[0097] Reference manufacturing example 1-1 Intermediate 2 represented by the following formula was produced in accordance with Reference Production Example 1, except that methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate was replaced with methyl (Z)-2-(5-bromo-2-methylbenzyl)-3-methoxyacrylate) produced by the method described in WO 2001 / 000562. [ka] Intermediate 2: 1 H-NMR (CDCl3) δ: 7.56-7.51 (2H, m), 7.47 (1H, s), 7.12 (1H, d), 3.85 (3H, s), 3.66 (3H, s), 3.57 (2H, s), 2.36 (3H, s), 1.32 (12H, s).

[0098] Reference manufacturing example 1-2 Intermediate 3 represented by the following formula was produced in accordance with Reference Production Example 1, except that (Z)-2-(5-bromo-2-chlorophenoxy)-3-methoxyacrylate produced by the method described in WO 98 / 03464 was used instead of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyacrylate. [ka] Intermediate 3: 1 H-NMR (CDCl3) δ: 7.38-7.37 (2H, m), 7.36 (1H, s), 7.19-7.17 (1H, m), 3.88 (3H, s), 3.72 (3H, s), 1.32 (12H, s).

[0099] Reference manufacturing example 2 To a mixture of 0.50 g of intermediate 1, 20 mL of ethanol, 20 mL of acetonitrile, and 20 mL of water, 0.43 g of metachloroperbenzoic acid (70% purity, containing 30% water) was added at room temperature and stirred for 3 hours. A saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of ammonium chloride were added successively to the resulting mixture, and the mixture was stirred for 1 hour. The resulting mixture was concentrated under reduced pressure and extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.29 g of intermediate A1 represented by the following formula: [ka] Intermediate A1: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 6.98 (1H, d), 6.37 (1H, dd), 6.28 (1H, d), 4.75 (1H, s), 3.86 (3H, s), 3.71 (3H, s), 2.25 (3H, s).

[0100] Reference manufacturing example 2-1 The compounds prepared according to Reference Preparation Example 2 and their physical properties are shown below. [ka] Intermediate A2: 1 H-NMR (CDCl3) δ: 7.48 (1H, s), 6.97 (1H, d), 6.61-6.54 (2H, m), 4.67 (1H, br s), 3.84 (3H, s), 3.68 (3H, s), 3.50 (2H, s), 2.27 (3H, s).

[0101] [ka] Intermediate A3: 1 H-NMR (DMSO-D6) δ: 9.69 (1H, br s), 7.61 (1H, s), 7.19 (1H, d), 6.40 (1H, dd), 6.26 (1H, d), 3.88 (3H, s), 3.66 (3H, s).

[0102] Reference manufacturing example 3 To a mixture of 0.50 g of methyl 2-(5-hydroxy-2-methylphenoxy)acetate, 0.82 g of triphenylphosphine, 0.39 mL of benzyl alcohol, and 10 mL of chloroform, 0.78 g of bis(2-methoxyethyl) azodicarboxylate was added at 0°C and stirred at room temperature for 22 hours. A saturated aqueous solution of sodium bicarbonate was added to the resulting mixture, which was then extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.55 g of intermediate C1, which is represented by the following formula: [ka] Intermediate C1: 1 H-NMR (CDCl3) δ: 7.45-7.30 (5H, m), 7.05 (1H, d), 6.52 (1H, dd), 6.38 (1H, d), 5.02 (2H, s), 4.62 (2H, s), 3.79 (3H, s), 2.22 (3H, s).

[0103] Reference manufacturing example 3-1 The compounds prepared according to Reference Preparation Example 3 and their physical properties are shown below. Formula (1b1) [ka] In the compound represented by the formula: wherein E is represented by the formula:

[0104] Intermediate C3 (E:Pr): 1 H-NMR (CDCl3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.62 (2H, s), 3.87 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.84-1.73 (2H, m), 1.02 (3H, t). Intermediate C4 (E:Bu): 1 H-NMR (CDCl3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 3.91 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.78-1.70 (2H, m), 1.53-1.42 (2H, m), 0.97 (3H, t). Intermediate C5(E:i-Bu): 1 H-NMR (CDCl3) δ: 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.63 (2H, s), 3.80 (3H, s), 3.66 (2H, d), 2.21 (3H, s), 2.11-1.99 (1H, m), 1.01 (6H, d). Intermediate C6 (E:Pen): 1H-NMR (CDCl3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.62 (2H, s), 3.90 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.82-1.70 (2H, m), 1.46-1.31 (4H, m), 0.93 (3H, t). Intermediate C7(E:CH2c-Pr): 1 H-NMR (CDCl3) δ: 7.02 (1H, d), 6.41 (1H, dd), 6.34 (1H, d), 4.62 (2H, s), 3.80 (3H, s), 3.74 (2H, d), 2.21 (3H, s), 1.31-1.18 (1H, m), 0.68-0.60 (2H, m), 0.37-0.29 (2H, m). Intermediate C8(E:CH2c-Pen): 1 H-NMR (CDCl3) δ: 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 4.63 (2H, s), 3.80 (3H, s), 3.77 (2H, d), 2.39-2.27 (1H, m), 2.21 (3H, s), 1.88-1.76 (2H, m), 1.67-1.53 ​​(4H, m), 1.40-1.28 (2H, m). Intermediate C9(E:CH2c-Hex): 1 H-NMR (CDCl3) δ: 7.02 (1H, d), 6.43 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 3.80 (3H, s), 3.70 (2H, d), 2.20 (3H, s), 1.90-1.80 (2H, m), 1.80-1.66 (4H, m), 1.35-1.14 (3H, m), 1.10-0.97 (2H, m). Intermediate C10 (E: CH2CH2Ph): 1H-NMR (CDCl3) δ: 7.36-7.21 (5H, m), 7.03 (1H, d), 6.44 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 4.13 (2H, t), 3.80 (3H, s), 3.08 (2H, t), 2.21 (3H, s). Intermediate C11(E:CH2C≡CH): 1 H-NMR (CDCl3) δ: 7.06 (1H, d), 6.52 (1H, dd), 6.38 (1H, d), 4.64 (2H, d), 4.62 (2H, s), 3.80 (3H, s), 2.52 (1H, t), 2.22 (3H, s).

[0105] Reference manufacturing example 4 To a mixture of 0.30 g of methyl 2-(5-hydroxy-2-methylphenoxy)acetate, 0.28 g of potassium carbonate, and 10 mL of DMF was added 0.29 g of N-methyl-N-phenylcarbamoyl chloride at room temperature and stirred for 3 hours. A saturated aqueous solution of ammonium chloride was added to the resulting mixture, followed by extraction with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.47 g of intermediate C2, represented by the following formula: [ka] Intermediate C2: 1 H-NMR (CDCl3) δ: 7.44-7.32 (4H, m), 7.30-7.23 (1H, m), 7.10 (1H, d), 6.72-6.45 (2H, m), 4.62 (2H, s), 3.80 (3H, s), 3.42 (3H, s), 2.25 (3H, s).

[0106] Reference manufacturing example 4-1 The compounds prepared according to Reference Preparation Example 4 and their physical properties are shown below. [ka] Intermediate C12: 1 H-NMR (CDCl3) δ: 7.11 (1H, d), 6.66 (1H, dd), 6.50 (1H, d), 4.63 (2H, s), 3.80 (3H, s), 3.08 (3H, s), 3.00 (3H, s), 2.25 (3H, s).

[0107] [ka] Intermediate C13: 1 H-NMR (CDCl3) δ: 7.10 (1H, d), 6.66 (1H, dd), 6.51 (1H, d), 4.62 (2H, s), 3.80 (3H, s), 3.47-3.32 (4H, m), 2.25 (3H, s), 1.28-1.16 (6H, m).

[0108] Reference manufacturing example 5 To a mixture of 0.24 g of intermediate C1, 0.15 g of methyl formate, and 5 mL of dimethoxyethane, 0.21 g of potassium tert-butoxide was added under ice cooling and stirred at room temperature for 1 hour. 1N hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate and concentrated under reduced pressure to obtain 0.19 g of intermediate B1 represented by the following formula: [ka] Intermediate B1: LCMS: 315 [M+H] + , RT = 1.90 minutes

[0109] Reference manufacturing example 5-1 The compounds prepared according to Reference Preparation Example 5 and their physical properties are shown below. Formula (1d1) [ka] In the compound represented by the formula: wherein E is represented by the formula:

[0110] Intermediate B2(E:Pen):LCMS: 295 [M+H] + , RT = 2.05 minutes Intermediate B3(E:CH2c-Pr):LCMS: 279 [M+H] + , RT = 1.82 minutes Intermediate B4(E:CH2c-Pen):LCMS: 307 [M+H] + , RT = 2.07 minutes Intermediate B5(E:CH2c-Hex):LCMS: 321 [M+H] + , RT = 2.16 minutes

[0111] Reference manufacturing example 6 To a mixture of 4.58 g of 5-bromo-2-methylbenzaldehyde and 185 mL of THF, 1.00 g of sodium hydride (60%, oil) was added under ice-cooling and stirred for 20 minutes. 5.00 g of methyl dimethylphosphonoacetate was added to the resulting mixture, and the mixture was stirred at room temperature for 4 hours. A saturated aqueous solution of sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 5.80 g of intermediate 4, which is represented by the following formula: [ka] Intermediate 4: 1 H-NMR (CDCl3) δ: 7.87 (1H, d), 7.66 (1H, d), 7.38 (1H, dd), 7.08 (1H, d), 6.35 (1H, d), 3.82 (3H, s), 2.37 (3H, s).

[0112] Reference manufacturing example 7 A mixture of 108.43 g of intermediate 4, 5.52 g of cobalt(II) chloride, and 1084 mL of methanol was cooled to -54°C, and 40.35 g of sodium borohydride was added thereto and stirred at -24°C for 6 hours. A 10% aqueous ammonium chloride solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 93.91 g of intermediate 5 represented by the following formula: [ka] Intermediate 5: 1 H-NMR (CDCl3) δ: 7.27-7.22 (2H, m), 7.01 (1H, d), 3.69 (3H, s), 2.90 (2H, t), 2.58 (2H, t), 2.26 (3H, s).

[0113] Reference manufacturing example 8 A mixture of 3.80 g of Intermediate 5 and 137 mL of THF was cooled to -72 °C, and 27 mL of lithium diisopropylamide (1.08 M hexane-THF solution) was added and stirred at -66 °C for 30 minutes. 7.10 g of methyl formate was added to the resulting mixture, and the mixture was stirred at -63 °C for 1 hour. 10% aqueous sodium hydrogen sulfate solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain crude methyl 2-(5-bromo-2-methylbenzyl)-3-hydroxyacrylate. 137 mL of DMF was added to the resulting crude methyl 2-(5-bromo-2-methylbenzyl)-3-hydroxyacrylate, and 6.13 g of potassium carbonate and 4.66 g of dimethyl sulfate were added sequentially. The mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3.61 g of intermediate E1 represented by the following formula. [ka] Intermediate E1

[0114] Reference manufacturing example 8-1 The compounds prepared according to Reference Preparation Example 8 and their physical properties are shown below. Formula (II-A): [ka] In the compound represented by the formula: 1 , X 2 and a compound in which L is any combination described in [Table II-A].

[0115] [Table 2] Intermediate E1: 1 H-NMR (CDCl3) δ: 7.49 (1H, s), 7.20 (2H, m), 6.97 (1H, d), 3.86 (3H, s), 2.68 (3H, s), 3.50 (2H, m), 2.28 (3H, s).

[0116] Reference manufacturing example 9 To a mixture of 2.00 g of 5-chloro-2-methylphenol, 2.33 g of potassium carbonate, and 20 mL of DMF, 2.58 g of methyl 2-bromoacetate was added and stirred at room temperature for 3 hours. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 2.94 g of intermediate 6 represented by the following formula: [ka] Intermediate 6: 1 H-NMR (CDCl3) δ: 7.07 (1H, dd), 6.89 (1H, dd), 6.68 (1H, d), 4.64 (2H, s), 3.81 (3H, s), 2.24 (3H, s).

[0117] Reference manufacturing example 10 To a mixture of 3.00 g of intermediate 6, 2.3 mL of methyl formate, and 20 mL of 1,2-dimethoxyethane, 3.15 g of potassium t-butoxide was added under ice cooling and stirred at room temperature for 2 hours. 1N hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2.44 g of intermediate 7, which is represented by the following formula: [ka] Intermediate 7: 1 H-NMR (CDCl3) δ: 7.53 (1H, d), 7.11 (1H, dt), 6.94 (1H, dd), 6.73 (1H, d), 5.76 (1H, d), 3.71 (3H, t), 2.32 (3H, s).

[0118] Reference manufacturing example 11 To a mixture of 1.09 g of intermediate 7, 0.70 g of potassium carbonate, and 10 mL of DMF, 0.62 mL of iodomethane was added under ice cooling and stirred at room temperature for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 1.00 g of intermediate D2 represented by the following formula: [ka] Intermediate D2

[0119] Reference manufacturing example 11-1 The compounds prepared according to Reference Preparation Example 11 and their physical properties are shown below. Formula (VI): [ka] In the compound represented by the formula: 1 and a compound in which L is any combination described in [Table VI].

[0120] [Table 3] Intermediate D1: 1 H-NMR (CDCl3) δ: 7.49 (1H, s), 7.06-7.01 (3H, m), 3.86 (3H, s), 3.68 (3H, s), 3.50 (2H, s), 2.31 (3H, s). Intermediate D2: 1 H-NMR (CDCl3) δ: 7.33 (1H, s), 7.07 (1H, dd), 6.88 (1H, dd), 6.70 (1H, d), 3.89 (3H, s), 3.72 (3H, s), 2.30 (3H, s).

[0121] Manufacturing Example 1 To a mixture of 0.25 g of Intermediate A1, 0.33 g of triphenylphosphine, 0.06 mL of ethanol, and 5 mL of chloroform, 0.32 g of bis(2-methoxyethyl) azodicarboxylate was added at 0°C and stirred at room temperature for 16 hours. A saturated aqueous solution of sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 0.23 g of Compound 1 of the present invention, which is represented by the following formula: [ka] Compound 1 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.33 (1H, d), 3.95 (2H, q), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.37 (3H, t).

[0122] Manufacturing Example 1-1 The compounds produced in accordance with Production Example 1 and their physical properties are shown below. Formula (1a1): [ka] In the compound represented by the formula: 1 and a compound in which L is any combination described in [Table 1-1] to [Table 1-6].

[0123] [Table 4]

[0124] [Table 5]

[0125] [Table 6]

[0126] [Table 7]

[0127] [Table 8]

[0128] [Table 9] Compound 2 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.45 (1H, dd), 6.31 (1H, d), 4.50-4.40 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.29 (6H, d). Compound 3 of the present invention: 1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.33 (1H, d), 3.86 (3H, s), 3.84 (2H, t), 3.70 (3H, s), 2.27 (3H, s), 1.82-1.71 (2H, m), 1.01 (3H, t). Compound 4 of this invention: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 3.63 (2H, d), 2.27 (3H, s), 2.09-1.97 (1H, m), 1.00 (6H, d). This compound 5: 1 H-NMR (CDCl3) δ: 7.33 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 3.88 (3H, s), 3.71 (3H, s), 3.50 (2H, s), 2.26 (3H, s), 1.00 (9H, s). Compound 6 of this invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.88 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.76-1.67 (2H, m), 1.52-1.40 (2H, m), 0.96 (3H, t). Compound 7 of this invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 4.30-4.22 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.74-1.62 (1H, m), 1.53-1.33 (3H, m), 1.24 (3H, d), 0.92 (3H, t). Compound 8 of this invention: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.86 (3H, s), 3.76-3.62 (2H, m), 3.70 (3H, s), 2.26 (3H, s), 1.86-1.76 (1H, m), 1.59-1.48 (1H, m), 1.29-1.17 (1H, m), 0.98 (3H, d), 0.93 (3H, t). Compound 9 of this invention: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.32 (1H, d), 3.90 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.84-1.75 (1H, m), 1.63 (2H, q), 0.94 (6H, d). Compound 10 of this invention: 1 H-NMR (CDCl3) δ: 7.32 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.32 (1H, d), 3.87 (3H, s), 3.77 (2H, d), 3.71 (3H, s), 2.27 (3H, s), 1.66-1.58 (1H, m), 1.52-1.36 (4H, m), 0.91 (6H, t). Compound 11 of this invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.78-1.69 (2H, m), 1.46-1.31 (4H, m), 0.92 (3H, t). This compound 12: 1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.43 (1H, dd), 6.37 (1H, d), 3.86 (3H, s), 3.72 (2H, d), 3.70 (3H, s), 2.27 (3H, s), 1.29-1.19 (1H, m), 0.63 (2H, q), 0.32 (2H, q). This compound 13: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.86 (3H, s), 3.74 (2H, d), 3.70 (3H, s), 2.36-2.26 (1H, m), 2.26 (3H, s), 1.87-1.75 (2H, m), 1.66-1.53 ​​(4H, m), 1.38-1.27 (2H, m). This compound 14: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.66 (2H, d), 2.26 (3H, s), 1.89-1.64 (6H, m), 1.34-1.15 (3H, m), 1.07-0.94 (2H, m). This compound 15: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.33 (1H, d), 3.95 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.63 (2H, q), 0.87-0.76 (1H, m), 0.50-0.43 (2H, m), 0.12-0.06 (2H, m). This compound 16: 1H-NMR (CDCl3) δ: 7.32 (1H, s), 7.04 (1H, d), 6.46 (1H, dd), 6.33 (1H, d), 4.69 (1H, t), 4.57 (1H, t), 4.02 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s), 2.20-2.06 (2H, m). This compound 17: 1 H-NMR (CDCl3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 4.12 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.63-2.51 (2H, m), 2.27 (3H, s). This compound 18: 1 H-NMR (CDCl3) δ: 7.32 (1H, s), 7.04 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.93 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.33-2.22 (2H, m), 2.27 (3H, s), 2.04-1.96 (2H, m). This compound 19: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.05 (1H, d), 6.45 (1H, dd), 6.36 (1H, d), 4.16 (2H, t), 3.87 (3H, s), 3.77 (2H, t), 3.71 (3H, s), 2.28 (3H, s). This compound 20: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.04 (1H, d), 6.46 (1H, dd), 6.32 (1H, d), 4.03 (2H, t), 3.87 (3H, s), 3.72 (2H, t), 3.71 (3H, s), 2.27 (3H, s), 2.23-2.15 (2H, m). This compound 21: 1H-NMR (CDCl3) δ: 7.29 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.40 (1H, d), 4.04 (2H, t), 3.86 (3H, s), 3.71 (2H, t), 3.69 (3H, s), 3.44 (3H, s), 2.27 (3H, s). This compound 22: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.04 (1H, d), 6.45 (1H, dd), 6.38 (1H, d), 4.14 (1H, dd), 3.91-3.85 (1H, m), 3.87 (3H, s), 3.71 (3H, s), 3.34-3.29 (1H, m), 2.91-2.87 (1H, m), 2.74 (1H, dd), 2.27 (3H, s). This compound 23: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.45 (1H, dd), 6.38 (1H, d), 4.27-4.19 (1H, m), 3.96-3.78 (4H, m), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 2.10-1.88 (3H, m), 1.77-1.67 (1H, m). This compound 24: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.35 (1H, d), 4.02 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.72 (2H, t), 2.53-2.43 (4H, m), 2.26 (3H, s), 1.64-1.56 (4H, m), 1.48-1.40 (2H, m). This compound 25: 1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.99 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.09 (2H, t), 0.06 (9H, s). This compound 26: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.33 (1H, d), 3.86 (3H, s), 3.83 (2H, t), 3.70 (3H, s), 2.27 (3H, s), 1.79-1.69 (2H, m), 0.60-0.54 (2H, m), 0.01 (9H, s). This compound 27: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.05 (1H, d), 6.44-6.38 (2H, m), 4.56 (2H, s), 3.87 (3H, s), 3.80 (3H, s), 3.71 (3H, s), 2.28 (3H, s). This compound 28: 1 H-NMR (CDCl3) δ: 7.46 (1H, s), 7.44-7.28 (5H, m), 7.02 (1H, d), 6.75 (1H, d), 6.69 (1H, dd), 4.99 (2H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s). This compound 29: 1 H-NMR (CDCl3) δ: 7.35-7.21 (6H, m), 7.03 (1H, d), 6.45 (1H, dd), 6.32 (1H, d), 4.09 (2H, t), 3.85 (3H, s), 3.70 (3H, s), 3.06 (2H, t), 2.27 (3H, s). This compound 30: 1H-NMR (CDCl3) δ: 7.40-7.34 (2H, m), 7.29 (1H, s), 7.09-7.01 (3H, m), 6.51 (1H, dd), 6.38 (1H, d), 4.93 (2H, s), 3.84 (3H, s), 3.69 (3H, s), 2.27 (3H, s). This compound 31: 1 H-NMR (CDCl3) δ: 7.39-7.30 (4H, m), 7.29 (1H, s), 7.14-6.98 (6H, m), 6.54 (1H, dd), 6.41 (1H, d), 4.94 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s). This compound 32: 1 H-NMR (CDCl3) δ: 7.66 (1H, t), 7.45 (1H, d), 7.31 (1H, s), 7.25 (1H, d), 7.04 (1H, d), 6.50 (1H, dd), 6.40 (1H, d), 5.09 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s). This compound 33: 1 H-NMR (CDCl3) δ: 8.76 (1H, s), 7.94 (1H, d), 7.70 (1H, d), 7.31 (1H, s), 7.07 (1H, d), 6.51 (1H, dd), 6.38 (1H, d), 5.08 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s). This compound 34: 1 H-NMR (CDCl3) δ: 7.33-7.29 (2H, m), 7.10-6.98 (3H, m), 6.54 (1H, dd), 6.41 (1H, d), 5.13 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s). This compound 35: 1H-NMR (CDCl3) δ: 7.78 (1H, d), 7.35 (1H, d), 7.31 (1H, s), 7.06 (1H, d), 6.55 (1H, dd), 6.44 (1H, d), 5.30 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s). This compound 36: 1 H-NMR (CDCl3) δ: 7.32 (1H, s), 7.07 (1H, d), 6.72 (1H, s), 6.49 (1H, dd), 6.38 (1H, d), 5.12 (2H, s), 4.44 (2H, q), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s), 1.41 (3H, t). This compound 37: 1 H-NMR (CDCl3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.46 (1H, dd), 6.37 (1H, d), 5.54-5.52 (1H, m), 5.42-5.40 (1H, m), 4.50 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.27 (3H, s). This compound 38: 1 H-NMR (CDCl3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.43 (1H, dd), 6.32 (1H, d), 6.11 (1H, t), 4.59 (2H, d), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s). This compound 39: 1 H-NMR (CDCl3) δ: 7.38-7.28 (6H, m), 7.01 (1H, d), 6.46 (1H, dd), 6.36 (1H, d), 5.12 (2H, s), 4.45 (2H, s), 3.85 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.97 (3H, s). This compound 71: 1H-NMR (CDCl3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.67 (1H, d), 6.61 (1H, dd), 3.85 (2H, t), 3.83 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.27 (3H, s), 1.82-1.71 (2H, m), 1.01 (3H, t). This compound 72: 1 H-NMR (CDCl3) δ: 7.33 (1H, s), 7.24 (1H, d), 6.48 (1H, dd), 6.39 (1H, d), 3.90-3.85 (5H, m), 3.72 (3H, s), 1.77-1.68 (2H, m), 1.52-1.41 (2H, m), 0.96 (3H, t). This compound 73: 1 H-NMR (CDCl3) δ: 7.48 (1H, s), 7.00 (1H, d), 6.67 (1H, d), 6.61 (1H, dd), 3.83 (3H, s), 3.67 (3H, s), 3.65 (2H, d), 3.51 (2H, s), 2.27 (3H, s), 2.09-1.98 (1H, m), 0.99 (6H, d). This compound 74: 1 H-NMR (CDCl3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.69-6.58 (2H, m), 3.88 (2H, t), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.27 (3H, s), 1.78-1.71 (2H, m), 1.47-1.30 (4H, m), 0.92 (3H, t). This compound 75: 1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.77-1.69 (2H, m), 1.46-1.24 (12H, m), 0.88 (3H, t). This compound 76: 1 H-NMR (CDCl3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.68 (1H, d), 6.60 (1H, dd), 3.83 (3H, s), 3.72 (2H, d), 3.66 (3H, s), 3.50 (2H, s), 2.26 (3H, s), 1.28-1.19 (1H, m), 0.64-0.58 (2H, m), 0.34-0.29 (2H, m). This compound 77: 1 H-NMR (CDCl3) δ: 7.42-7.24 (7H, m), 6.57 (1H, dd), 6.48 (1H, d), 4.98 (2H, s), 3.84 (3H, s), 3.70 (3H, s). This compound 78: 1 H-NMR (CDCl3) δ: 7.47 (1H, s), 7.34-7.19 (5H, m), 7.00 (1H, d), 6.69 (1H, d), 6.62 (1H, dd), 4.11 (2H, t), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 3.06 (2H, t), 2.27 (3H, s). This compound 79: 1 H-NMR (CDCl3) δ: 7.36-7.21 (7H, m), 6.48 (1H, dd), 6.39 (1H, d), 4.09 (2H, t), 3.86 (3H, s), 3.71 (3H, s), 3.06 (2H, t). This compound 80: 1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.29-7.25 (2H, m), 7.21-7.15 (3H, m), 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.91-3.87 (2H, m), 3.85 (3H, s), 3.69 (3H, s), 2.70-2.63 (2H, m), 2.26 (3H, s), 1.80-1.75 (4H, m). This compound 81: 1 H-NMR (CDCl3) δ: 7.48 (1H, s), 7.01 (1H, d), 6.70 (1H, d), 6.63 (1H, dd), 6.10-5.98 (1H, m), 5.42-5.34 (1H, m), 5.28-5.23 (1H, m), 4.49-4.45 (2H, m), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.28 (3H, s). This compound 82: 1 H-NMR (CDCl3) δ: 7.48 (1H, s), 7.03 (1H, d), 6.75 (1H, d), 6.69 (1H, dd), 4.62 (2H, d), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.49 (1H, t), 2.29 (3H, s). This compound 83: 1 H-NMR (CDCl3) δ: 7.46 (1H, s), 7.34 (2H, d), 7.02 (1H, d), 6.90 (2H, d), 6.74 (1H, d), 6.69 (1H, dd), 4.91 (2H, s), 3.82 (3H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s). This compound 84: 1H-NMR (CDCl3) δ: 7.46 (1H, s), 7.36-7.28 (1H, m), 7.20-7.12 (2H, m), 7.04-6.95 (2H, m), 6.73 (1H, d), 6.67 (1H, dd), 4.99 (2H, s), 3.82 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s). This compound 85: 1 H-NMR (CDCl3) δ: 7.47 (1H, s), 7.31-7.27 (1H, m), 7.10-6.96 (3H, m), 6.75 (1H, d), 6.70 (1H, dd), 5.14 (2H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s). This compound 86: 1 H-NMR (CDCl3) δ: 7.49-7.46 (1H, m), 7.42-7.40 (1H, m), 7.29 (1H, s), 7.05 (1H, d), 6.52 (1H, dd), 6.47-6.45 (1H, m), 6.39 (1H, d), 4.85 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s). This compound 87: 1 H-NMR (CDCl3) δ: 8.58-8.55 (2H, m), 7.32 (1H, s), 7.07 (1H, d), 6.52 (1H, dd), 6.42 (1H, d), 5.14 (2H, s), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s). This compound 88: 1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.52-6.46 (1H, m), 6.36-6.27 (1H, m), 4.17-3.98 (2H, m), 3.87 (3H, s), 3.85-3.65 (1H, m), 3.71 (3H, s), 3.43-3.27 (2H, m), 2.26 (3H, s), 2.06-1.77 (4H, m), 1.47 (9H, s).

[0129] Manufacturing Example 2 To a mixture of 0.29 g of Intermediate A1, 0.25 g of potassium carbonate, and 10 mL of DMF was added 0.16 mL of benzyl bromide at room temperature and stirred for 3 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 0.31 g of the present compound 40 represented by the following formula. [ka] Compound 40 of the present invention: 1 H-NMR (CDCl3) δ: 7.44-7.29 (5H, m), 7.29 (1H, s), 7.05 (1H, d), 6.53 (1H, dd), 6.41 (1H, d), 4.98 (2H, s), 3.84 (3H, s), 3.69 (3H, s), 2.27 (3H, s).

[0130] Manufacturing Example 2-1 The compounds produced according to Production Example 2 and their physical properties are shown below. In the compound represented by formula (1a1), E, ​​R 1 and a compound in which L is any combination described in [Table 2-1].

[0131] [Table 10] Compound 41 of the present invention: 1H-NMR (CDCl3) δ: 7.70-7.64 (2H, m), 7.61 (1H, t), 7.41 (1H, t), 7.32 (1H, s), 7.06 (1H, d), 6.55 (1H, dd), 6.42 (1H, d), 5.19 (2H, s), 3.87 (3H, s), 3.69 (3H, s), 2.28 (3H, s). This compound 42: 1 H-NMR (CDCl3) δ: 7.74 (1H, s), 7.66-7.58 (2H, m), 7.48 (1H, t), 7.32 (1H, s), 7.06 (1H, d), 6.49 (1H, dd), 6.39 (1H, d), 5.00 (2H, s), 3.87 (3H, s), 3.70 (3H, s), 2.28 (3H, s). This compound 43: 1 H-NMR (CDCl3) δ: 7.67 (2H, d), 7.52 (2H, d), 7.30 (1H, s), 7.06 (1H, d), 6.48 (1H, dd), 6.38 (1H, d), 5.04 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s). This compound 44: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.06 (1H, d), 6.52 (1H, dd), 6.41 (1H, d), 4.61 (2H, d), 3.86 (3H, s), 3.70 (3H, s), 2.50 (1H, t), 2.28 (3H, s). This compound 45: 1 H-NMR (CDCl3) δ: 7.33 (1H, s), 7.05 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 4.00 (2H, t), 3.88 (3H, s), 3.72 (3H, s), 2.57 (2H, t), 2.28 (3H, s), 2.14-2.05 (2H, m).

[0132] Manufacturing example 3 To a mixture of 0.20 g of Intermediate A1, 0.15 g of potassium carbonate, and 5 mL of DMF was added 0.09 mL of dimethylcarbamoyl chloride at room temperature and stirred for 19 hours. A saturated aqueous solution of ammonium chloride was added to the resulting mixture, followed by extraction with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:3) to obtain 0.08 g of the present invention compound 46, represented by the following formula: [ka] Compound 46 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.68 (1H, dd), 6.50 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.06 (3H, s), 2.98 (3H, s), 2.31 (3H, s).

[0133] Manufacturing Example 3-1 The compounds produced in accordance with Production Example 3 and their physical properties are shown below. In the compound represented by formula (1a1), E, ​​R 1 and a compound in which L is any combination described in [Table 3-1].

[0134] [Table 11] Compound 47 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71-6.65 (1H, m), 6.52-6.49 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 3.47-3.34 (2H, m), 3.03 (1.5H, s), 2.96 (1.5H, s), 2.31 (3H, s), 1.24-1.13 (3H, m). Compound 48 of the present invention: 1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.68 (1H, dd), 6.51 (1H, d), 3.86 (3H, s), 3.71 (3H, s), 3.44-3.32 (4H, m), 2.31 (3H, s), 1.25-1.14 (6H, m). This compound 49: 1 H-NMR (CDCl3) δ: 7.42-7.30 (4H, m), 7.29 (1H, s), 7.27-7.22 (1H, m), 7.09 (1H, d), 6.75-6.61 (1H, br m), 6.51 (1H, br s), 3.85 (3H, s), 3.69 (3H, s), 3.40 (3H, s), 2.30 (3H, s). This compound 50: 1 H-NMR (CDCl3) δ: 7.45 (1H, s), 7.41-7.32 (4H, m), 7.25-7.21 (1H, m), 7.06 (1H, d), 6.86-6.77 (2H, m), 3.83 (3H, s), 3.65 (3H, s), 3.51 (2H, s), 3.41 (3H, s), 2.30 (3H, s). This compound 51: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71 (1H, dd), 6.54 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.52 (2H, t), 3.45 (2H, t), 2.31 (3H, s), 1.98-1.85 (4H, m). This compound 52: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.67 (1H, dd), 6.50 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.62-3.43 (4H, br m), 2.30 (3H, s), 1.69-1.52 (6H, m). This compound 89: 1H-NMR (CDCl3) δ: 7.46 (1H, s), 7.07 (1H, d), 6.85-6.80 (2H, m), 3.83 (3H, s), 3.66 (3H, s), 3.52 (2H, s), 3.07 (3H, s), 2.99 (3H, s), 2.31 (3H, s). Compound 90 of the present invention: 1 H-NMR (CDCl3) δ: 7.46 (1H, s), 7.07 (1H, d), 6.87-6.80 (2H, m), 3.83 (3H, s), 3.67 (3H, s), 3.53 (2H, s), 3.46-3.32 (4H, m), 2.31 (3H, s), 1.27-1.15 (6H, m).

[0135] Manufacturing Example 4 To a mixture of 0.25 g of Intermediate A1, 0.10 g of triphosgene, and 5 mL of chloroform was added 0.18 mL of N,N-diisopropylethylamine at room temperature and stirred for 2 hours. To the resulting mixture, 0.11 mL of propylamine and 0.27 mL of N,N-diisopropylethylamine were added sequentially and stirred for 16 hours. Water was added to the resulting mixture, followed by extraction with ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 0.18 g of the present invention compound 53, represented by the following formula: [ka] Compound 53 of the present invention: 1 H-NMR (CDCl3) δ: 7.29 (1H, s), 7.10 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.97-4.88 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.20 (2H, q), 2.30 (3H, s), 1.63-1.52 (2H, m), 0.95 (3H, t).

[0136] Manufacturing Example 4-1 The compounds produced according to Production Example 4 and their physical properties are shown below. In the compound represented by formula (1a1), E, ​​R 1 and a compound in which L is any combination described in [Table 4-1].

[0137] [Table 12] Compound 54 of the present invention: 1 H-NMR (CDCl3) δ: 7.29 (1H, s), 7.10 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.94-4.83 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.24 (2H, q), 2.30 (3H, s), 1.58-1.48 (2H, m), 1.43-1.32 (2H, m), 0.94 (3H, t). Compound 55 of the present invention: 1 H-NMR (CDCl3) δ: 7.29 (1H, s), 7.10 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.93-4.85 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.23 (2H, q), 2.30 (3H, s), 1.59-1.50 (2H, m), 1.38-1.28 (4H, m), 0.91 (3H, t). Compound 56 of the present invention: 1 H-NMR (CDCl3) δ: 7.29 (1H, s), 7.09 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.83-4.76 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.58-3.47 (1H, m), 2.30 (3H, s), 2.02-1.94 (2H, m), 1.77-1.66 (2H, m), 1.65-1.57 (1H, m), 1.42-1.29 (2H, m), 1.26-1.12 (3H, m). Compound 57 of the present invention: 1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71-6.63 (1H, m), 6.52-6.47 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 3.38-3.25 (2H, m), 3.03 (1.4H, s), 2.97 (1.6H, s), 2.31 (3H, s), 1.68-1.58 (2H, m), 0.98-0.90 (3H, m). Compound 58 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71-6.64 (1H, m), 6.51-6.49 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 3.41-3.28 (2H, m), 3.03 (1.4H, s), 2.96 (1.6H, s), 2.30 (3H, s), 1.64-1.52 (2H, m), 1.41-1.30 (2H, m), 0.98-0.92 (3H, m). Compound 59 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.13 (1H, d), 6.71 (1H, dd), 6.55 (1H, d), 3.86 (3H, s), 3.78 (3H, s), 3.70 (3H, s), 3.26 (3H, s), 2.32 (3H, s).

[0138] Manufacturing Example 5 To a mixture of 0.20 g of Intermediate A1, 0.09 mL of propionyl chloride, and 5 mL of chloroform was added 0.17 mL of triethylamine at room temperature and stirred for 16 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:4) to obtain 0.18 g of the present invention compound 60 represented by the following formula. [ka] Compound 60 of the present invention: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.13 (1H, d), 6.66 (1H, dd), 6.48 (1H, d), 3.86 (3H, s), 3.71 (3H, s), 2.54 (2H, q), 2.32 (3H, s), 1.24 (3H, t).

[0139] Manufacturing Example 5-1 The compounds produced according to Production Example 5 and their physical properties are shown below. In the compound represented by formula (1a1), E, ​​R 1 and a compound in which L is any combination described in [Table 5-1].

[0140] [Table 13] Compound 61 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.11 (1H, d), 6.63 (1H, dd), 6.44 (1H, d), 3.85 (3H, s), 3.70 (3H, s), 2.49 (1H, tt), 2.31 (3H, s), 2.07-1.98 (2H, m), 1.85-1.75 (2H, m), 1.71-1.63 (1H, m), 1.61-1.47 (2H, m), 1.39-1.20 (3H, m). Compound 62 of the present invention: 1 H-NMR (CDCl3) δ: 8.17 (2H, d), 7.62 (1H, t), 7.49 (2H, t), 7.31 (1H, s), 7.18 (1H, d), 6.79 (1H, dd), 6.60 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 2.35 (3H, s). Compound 63 of the present invention: 1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.14 (1H, d), 6.76 (1H, dd), 6.57 (1H, d), 4.29 (2H, q), 3.87 (3H, s), 3.71 (3H, s), 2.32 (3H, s), 1.37 (3H, t). This compound 64: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 7.12 (1H, d), 6.77 (1H, dd), 6.55 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 2.31 (3H, s), 1.54 (9H, s). This compound 65: 1 H-NMR (CDCl3) δ: 7.33 (1H, s), 7.17 (1H, d), 6.83 (1H, dd), 6.68 (1H, d), 3.88 (3H, s), 3.72 (3H, s), 3.07 (3H, s), 2.34 (3H, s). This compound 66: 1 H-NMR (CDCl3) δ: 7.33 (1H, s), 7.16 (1H, d), 6.81 (1H, dd), 6.66 (1H, d), 3.88 (3H, s), 3.72 (3H, s), 3.18-3.12 (2H, m), 2.33 (3H, s), 2.03-1.91 (2H, m), 1.09 (3H, t). This compound 67: 1 H-NMR (CDCl3) δ: 7.80 (2H, t), 7.64 (1H, t), 7.50 (2H, t), 7.25 (1H, s), 7.01 (1H, d), 6.46 (1H, dd), 6.42 (1H, d), 3.85 (3H, s), 3.70 (3H, s), 2.28 (3H, s).

[0141] Manufacturing example 6 To a mixture of 0.18 g of Intermediate A1, 0.11 g of dimethylthiocarbamoyl chloride, and 5 mL of DMF was added 0.05 g of sodium hydride (60%, oil) at room temperature and stirred for 4 hours. A saturated aqueous solution of ammonium chloride was added to the resulting mixture, followed by extraction with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:3) to obtain 0.12 g of the present invention compound 68, represented by the following formula: [ka] Compound 68 of the present invention: 1 H-NMR (CDCl3) δ: 7.30 (1H, s), 7.15 (1H, d), 6.63 (1H, dd), 6.48 (1H, d), 3.86 (3H, s), 3.71 (3H, s), 3.44 (3H, s), 3.31 (3H, s), 2.33 (3H, s).

[0142] Manufacturing Example 6-1 The compounds prepared according to Preparation Example 6 and their physical properties are shown below. In the compound represented by formula (1a1), E, ​​R 1 and a compound in which L is any combination described in [Table 6-1].

[0143] [Table 14] Compound 69 of the present invention: 1 H-NMR (CDCl3) δ: 7.33 (1H, s), 7.14 (1H, d), 6.83 (1H, dd), 6.69 (1H, d), 3.88 (3H, s), 3.71 (3H, s), 2.90 (6H, s), 2.32 (3H, s). Compound 70 of the present invention: 1H-NMR (CDCl3) δ: 7.33 (1H, s), 7.13 (1H, d), 6.81 (1H, dd), 6.67 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 3.30 (4H, q), 2.32 (3H, s), 1.16 (6H, t).

[0144] Manufacturing Example 7 To a mixture of 0.19 g of Intermediate B1, 0.10 g of potassium carbonate, and 5 mL of DMF, 0.10 mL of iodomethane was added at 0°C and stirred for 1 hour. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 0.09 g of the present compound 40 represented by the following formula.

[0145] Manufacturing Example 8 A mixture of 0.03 g of intermediate D2, 0.02 g of benzyl alcohol, 0.001 g of palladium(II) acetate, 0.002 g of 2-(di-t-butylphosphino)-1,1'-binaphthyl, 0.08 g of cesium carbonate, and 2 mL of toluene was stirred at 40°C for 15 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 0.03 g of a crude product containing compound 40 of the present invention. Compound 40 of the present invention: LCMS: 329 [M+H] + , RT = 2.08 minutes

[0146] Manufacturing Example 9 A mixture of 0.05 g of intermediate D1, 0.04 g of benzyl alcohol, 0.01 g of tBuBrettPhos Pd G3, 0.03 g of sodium tert-butoxide, and 2 mL of dioxane was stirred at 80 °C for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 0.05 g of a crude product containing compound 28 of the present invention. Inventive compound 28: LCMS: 327 [M+H] +, RT = 2.22 minutes

[0147] Next, examples of the compounds of the present invention and intermediates produced according to any of the production examples described in the Examples and the production methods described in this specification are shown below.

[0148] Formula (1A): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X1 is any substituent selected from group X (hereinafter referred to as compound group SX1).

[0149] Group X: Et, Pr, i-Pr, (CH2)3CH3, CH2CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2c-Pr, (CH2)4CH3, (CH2)2CH(CH3)2, CH(CH3)(CH2)2CH3, CH(CH2CH3)CH2CH3, CH2CH(CH3)CH2CH3, C(CH3)2CH2CH3, CH2C(CH3)3, CH2c-Bu, CH2c-Pen, CH2c-Hex, (CH2)2c-Pr, (1-methylcyclopropyl)methyl, (2-methylcyclopropyl)methyl, 1-cyclopropylethyl, (CH2)3c-Pr, (CH2)5CH3, (CH2)3CH(CH3)2, (CH2)2CH(CH3)CH2CH3, CH2CH(CH3)(CH2)2CH3, CH(CH3)(CH2)3CH3, CH2CH(CH2CH3)2, heptyl, octyl, nonyl, decyl, CH2CH=CH2, CH2CH=CHCH3, CH2CH=C(CH3)2, CH2CH=CF2, CH2CH=CCl2, CH2CH=CHCH2CH3, CH2CH=CH(CH2)2CH3, CH2C(CH3)=CH2, CH2C(CH3)=CHCH3, CH2C(CH3)=C(CH3)2, CH2C(CH3)=CHCH2CH3, CH2C(CH3)=CH(CH2)2CH3, CH2CF=CH2, CH2CF=CHCH3, CH2CF=C(CH3)2, CH2CF=CF2, CH2CF=CHCH2CH3, CH2CF=CH(CH2)2CH3, CH2CCl=CH2, CH2CCl=CHCH3, CH2CCl=C(CH3)2, CH2CCl=CCl2, CH2CCl=CHCH2CH3, CH2CCl=CH(CH2)2CH3, (CH2)2CH=CH2, (CH2)2CH=CHCH3, (CH2)2CH=CHCH2CH3, (CH2)2CH=C(CH3)2, (CH2)2C(CH3)=CH2, (CH2)2C(CH3)=CHCH3, (CH2)2C(CH3)=CHCH2CH3, (CH2)2C(CH3)=C(CH3)2, (CH2)3CH=CH2, (CH2)3C(CH3)=CH2, (CH2)4CH=CH2, (CH2)4C(CH3)=CH2, CH2C≡CH, CH2C≡CCH3, CH2C≡CCH2CH3, CH2C≡Cc-Pr,CH2C≡CPh,(CH2)2C≡CH,(CH2)2C≡CCH3,(CH2)2C≡CCH2CH3,(CH2)2C≡Cc-Pr ,(CH2)2C≡CPh,(CH2)3C≡CH,(CH2)3C≡CCH3,(CH2)3C≡CCH2CH3,(CH2)3C≡Cc -Pr,(CH2)3C≡CPh,CH2Cl,CH2Br,CH2CN,CH2OCH3,CH2OCH2CH3,CH2O(CH2)2CH3,CH2OPh,CH2SCH3,CH2S(O)CH3,CH2S(O)2CH3,CH2SCH2CH3,CH2S(O)CH 2CH3,CH2S(O)2CH2CH3,CH2S(CH2)2CH3,CH2S(O)(CH2)2CH3,CH2S(O)2(CH2)2CH3,CH2SPh,CH2S(O)Ph,CH2S(O)2Ph,CH2C(O)CH3,CH2C(O)CH2CH3,CH2C(O)Ph,CH2C(O)NH2,CH2C(O)NHCH3,CH2C(O)N(CH3)2,CH2C(O)NHPh,CH2C(O)N(CH3)Ph,CH2C(O)OCH3,CH2C(O)OCH2CH3,CH2OC(O)Ph,CH2OC(O)OCH3, CH2OC(O)OCH2CH3,CH2OC(O)OPh,CH2OC(O)NHCH3,CH2OC(O)NHCH2CH3,CH2OC(O)NHPh,CH2OC(O)N(CH3)2,CH2OC(O)N(CH3)CH2CH3,CH2OC(O)N(CH3)Ph ,CH2OC(O)N(CH2CH3)2,CH2(2-oxiranyl),CH2(2-tetrahydrofuranyl),CH2(2-tetrahydropyranyl),CH2CH=NOCH3,CH2CH=NOCH2CH3,CH2CH=NOCH2P h,CH2C(CH3)=NOCH3,CH2C(CH3)=NOCH2CH3,CH2C(CH3)=NOCH2Ph,(CH2)2F,CH2CF3,(CH2)2Cl,CH2CCl3,(CH2)2Br,(CH2)2I,CH2Si(CH3)3,(CH2)2CF3 ,(CH2)2CN,(CH2)2NO2,(CH2)2Si(CH3)3,(CH2)2OCH3,(CH2)2OCH2CH3,(CH2)2SCH3,(CH2)2SCH2CH3,(CH2)2SPh,(CH2)2S(O)CH3,(CH2)2S(O)CH2CH3,(CH2)2S(O)Ph,(CH2)2S(O)2CH3,(CH2)2S(O)2CH2CH3,(CH2)2S(O)2Ph,(CH2)2NHCH3,(CH2)2N(CH3)2,(CH2)2NHPh,(CH2)2NHCH2Ph,(CH2)2N(CH3)C H2Ph,(CH2)2C(O)CH3,(CH2)2C(O)CH2CH3,(CH2)2C(O)Ph,(CH2)2S(O)2NHCH3,(CH2)2S(O)2N(CH3)2,(CH2)2S(O)2NHPh,(CH2)2S(O)2N(CH3)Ph,(CH2 )2C(O)NH2,(CH2)2C(O)NHCH3,(CH2)2C(O)N(CH3)2,(CH2)2C(O)NHPh,(CH2)2C(O)N(CH3)Ph,(CH2)2C(O)OCH3,(CH2)2C(O)OCH2CH3,(CH2)2NHC(O)CH3,(CH2)2NHC(O)OCH2CH3,(CH2)2NHC(O)Ph,(CH2)2NCH3C(O)CH3,(CH2)2NCH3C(O)Ph,(CH2)2NHC(O)OCH3,(CH2)2NHC(O)OCH 2CH3,(CH2)2NHC(O)OPh,(CH2)2NCH3C(O)OCH3,(CH2)2NCH3C(O)OCH2CH3,(CH2)2NCH3C(O)OPh,(CH2)2NHC(O)NHCH3,(CH2)2NHC(O)NHCH2CH3,(CH2)2NHC(O)NHPh,(CH2)2NHC(O)N(CH3)2,(CH2)2NHC(O)N(CH3)CH2CH3,(CH2)2NHC(O)N(CH3)Ph,(CH2)2NHC(O)N(CH2CH3)2,(CH2)2NCH3C(O)NHCH3,(CH2 )2NCH3C(O)NHCH2CH3,(CH2)2NCH3C(O)NHPh,(CH2)2NCH3C(O)N(CH3)2,(CH2)2NCH3C(O)N(CH3)CH2CH3,(CH2)2NCH3C(O)N(CH3)Ph,(CH2)2NCH3C(O)N(CH2CH3)2,(CH2)2OC(O)CH3,(CH2)2OC(O)CH2CH3,(CH2)2OC(O)Ph,(CH2)2OC(O)OCH3,(CH2)2OC(O)OCH2CH3,(CH2)2OC(O)OPh,(CH2)2OC(O)NHCH3,(CH2)2OC(O)NHCH2CH3,(CH2)2OC(O)NHPh,(CH2)2OC(O)N(CH3)2,(CH2)2OC(O)N(CH3)CH2CH3,(CH2)2OC(O)N(CH3)Ph,(CH2)2OC(O)N(CH2CH3)2,(CH 2)2S(O)2NHCH3,(CH2)2S(O)2NHCH2CH3,(CH2)2S(O)2NHPh,(CH2)2S(O)2N(CH3)2,(CH2)2S(O)2N(CH3)CH2CH3,(CH2)2S(O)2N(CH3)Ph,(CH2)2S(O), 2N(CH2CH3)2,(CH2)3F,(CH2)3Cl,(CH2)3Br,(CH2)3I,(CH2)3CF3,(CH2)3CN,(CH2)3NO 2,(CH2)3Si(CH3)3,(CH2)3OCH3,(CH2)3OCH2CH3,(CH2)3SCH3,(CH2)3SCH2CH3,(CH2)3 NHCH3,(CH2)3N(CH3)2,(CH2)4F,(CH2)4Cl,(CH2)4CF3,(CH2)4CN,(CH2)4NO2,(CH2)4P h,(CH2)4OCH3,(CH2)4SCH3,(CH2)4NHCH3,(CH2)4N(CH3)2,(CH2)5F,(CH2)5Cl,(CH2)5C F3,(CH2)5CN,(CH2)5NO2,(CH2)5Ph,(CH2)5OCH3,(CH2)5SCH3,(CH2)5NHCH3,(CH2)5N( CH3)2,(CH2)6F,(CH2)6Cl,(CH2)6CF3,(CH2)6CN,(CH2)6NO2,(CH2)6Ph,(CH2)6OCH3,(C A group consisting of H2)6SCH3,(CH2)6NHCH3,(CH2)6N(CH3)2,CH2CF2CF3,(CH2)2CF2CF3,CH2(CF2)2CF3,(CH2)2CF(CF3)2,(CH2)2(CF2)5CF3,CF3,CF2CHF(CF3),CF2CHF(OCF3),CH2CF2CF2H.

[0150] In the compound represented by formula (1A), R 1 is a chlorine atom, L is an oxygen atom, and R X1 is any substituent selected from group X (hereinafter referred to as compound group SX2).

[0151] In the compound represented by formula (1A), R 1 is a methyl group, L is CH2, and R X1 is any substituent selected from group X (hereinafter referred to as compound group SX3).

[0152] In the compound represented by formula (1A), R 1 is a chlorine atom, L is CH2, and R X1 is any substituent selected from group X (hereinafter referred to as compound group SX4).

[0153] Formula (1B): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, m is 1, and R X2 , R X3 , R X4 , R X5 and R X6 Compounds in which the above is any of the combinations described in Combination A (hereinafter, referred to as compound group SX5).

[0154] Combination A consists of substituent numbers ZA1 to ZA311. Substituent numbers ZA1 to ZA311 refer to R in the compound represented by formula (1B), the compound represented by formula (2B), and the compound represented by formula (3B). X2 , R X3 , R X4 , R X5 and R X6 The following represents a combination of [substituent number; R X2 ,R X3 ,R X4 ,R X5 ,R X6 For example, the substituent number ZA2 is R X2 is a methyl group, and R X3 , R X4 , R X5 and R X6 is a hydrogen atom.

[0155] Combination A [ZA1;H,H,H,H,H],[ZA2;Me,H,H,H,H],[ZA3;F,H,H,H,H],[ZA4;Cl,H,H,H,H],[ZA5;OMe,H,H,H,H],[ZA6;CF3,H,H,H,H],[ZA7;H,Me,H,H,H],[ZA8;H,Et,H,H,H],[ZA9;H,Pr,H,H,H],[ZA10;H,i-Pr,H,H,H],[ZA11;H,t-Bu,H,H,H],[ZA12;H,OMe,H,H,H],[ZA13;H,OEt,H,H,H],[ZA14;H,OPr,H,H,H],[ZA15;H,Oi-Pr,H,H,H],[ZA16;H,CF3,H,H,H],[ZA17;H,CF2H,H,H,H],[ZA18;H,CFH2,H,H,H],[ZA19;H,F,H,H,H],[ZA20;H,Cl,H,H,H],[ZA21;H,Br,H,H,H],[ZA22;H,CN,H,H,H],[ZA23;H,Ph,H,H,H],[ZA24;H,OPh,H,H,H],[ZA25;H,c-Pr,H,H,H],[ZA26;H,c-Pen,H,H,H],[ZA27;H,c-Hex,H,H,H],[ZA28;H,H,Me,H,H],[ZA29;H,H,Et,H,H],[ZA30;H,H,Pr,H,H],[ZA31;H,H,i-Pr,H,H],[ZA32;H,H,t-Bu,H,H],[ZA33;H,H,OMe,H,H],[ZA34;H,H,OEt,H,H],[ZA35;H,H,OPr,H,H],[ZA36;H,H,Oi-Pr,H,H],[ZA37;H,H,CF3,H,H],[ZA38;H,H,CF2H,H,H],[ZA39;H,H,CFH2,H,H],[ZA40;H,H,F,H,H],[ZA41;H,H,Cl,H,H],[ZA42;H,H,Br,H,H],[ZA43;H,H,CN,H,H],[ZA44;H,H,Ph,H,H],[ZA45;H,H,OPh,H,H],[ZA46;H,H,c-Pr,H,H],[ZA47;H,H,c-Pen,H,H],[ZA48;H,H,c-Hex,H,H],[ZA49;H,H,H,H,F],[ZA50;Me,H,H,H,F],[ZA51;F,H,H,H,F],[ZA52;Cl,H,H,H,F],[ZA53;H,Me,H,H,F],[ZA54;H,Et,H,H,F],[ZA55;H,Pr,H,H,F],[ZA56;H,i-Pr,H,H,F],[ZA57;H,t-Bu,H,H,F],[ZA58;H,OMe,H,H,F],[ZA59;H,OEt,H,H,F],[ZA60;H,OPr,H,H,F],[ZA61;H,Oi-Pr,H,H,F],[ZA62;H,CF3,H,H,F],[ZA63;H,CF2H,H,H,F],[ZA64;H,CFH2,H,H,F],[ZA65;H,F,H,H,F],[ZA66;H,Cl,H,H,F],[ZA67;H,Br,H,H,F],[ZA68;H,CN,H,H,F],[ZA69;H,Ph,H,H,F],[ZA70;H,OPh,H,H,F],[ZA71;H,c-Pr,H,H,F],[ZA72;H,c-Pen,H,H,F],[ZA73;H,c-Hex,H,H,F],[ZA74;H,H,Me,H,F],[ZA75;H,H,Et,H,F],[ZA76;H,H,Pr,H,F],[ZA77;H,H,i-Pr,H,F],[ZA78;H,H,t-Bu,H,F],[ZA79;H,H,OMe,H,F],[ZA80;H,H,OEt,H,F],[ZA81;H,H,OPr,H,F],[ZA82;H,H,Oi-Pr,H,F],[ZA83;H,H,CF3,H,F],[ZA84;H,H,CF2H,H,F],[ZA85;H,H,CFH2,H,F],[ZA86;H,H,F,H,F],[ZA87;H,H,Cl,H,F],[ZA88;H,H,Br,H,F],[ZA89;H,H,CN,H,F],[ZA90;H,H,Ph,H,F],[ZA91;H,H,OPh,H,F],[ZA92;H,H,c-Pr,H,F],[ZA93;H,H,c-Pen,H,F],[ZA94;H,H,c-Hex,H,F],[ZA95;H,H,H,H,Cl],[ZA96;Me,H,H,H,Cl],[ZA97;F,H,H,H,Cl],[ZA98;Cl,H,H,H,Cl],[ZA99;H,Me,H,H,Cl],[ZA100;H,Et,H,H,Cl];

[0156] [ZA101;H,Pr,H,H,Cl],[ZA102;H,i-Pr,H,H,Cl],[ZA103;H,t-Bu,H,H,Cl],[ZA104;H,OMe,H,H,Cl],[ZA105;H,OEt,H,H,Cl],[ZA106;H,OPr,H,H,Cl],[ZA107;H,Oi-Pr,H,H,Cl],[ZA108;H,CF3,H,H,Cl],[ZA109;H,CF2H,H,H,Cl],[ZA110;H,CFH2,H,H,Cl],[ZA111;H,F,H,H,Cl],[ZA112;H,Cl,H,H,Cl],[ZA113;H,Br,H,H,Cl],[ZA114;H,CN,H,H,Cl],[ZA115;H,Ph,H,H,Cl],[ZA116;H,OPh,H,H,Cl],[ZA117;H,c-Pr,H,H,Cl],[ZA118;H,c-Pen,H,H,Cl],[ZA119;H,c-Hex,H,H,Cl],[ZA120;H,H,Me,H,Cl],[ZA121;H,H,Et,H,Cl],[ZA122;H,H,Pr,H,Cl],[ZA123;H,H,i-Pr,H,Cl],[ZA124;H,H,t-Bu,H,Cl],[ZA125;H,H,OMe,H,Cl],[ZA126;H,H,OEt,H,Cl],[ZA127;H,H,OPr,H,Cl],[ZA128;H,H,Oi-Pr,H,Cl],[ZA129;H,H,CF3,H,Cl],[ZA130;H,H,CF2H,H,Cl],[ZA131;H,H,CFH2,H,Cl],[ZA132;H,H,F,H,Cl],[ZA133;H,H,Cl,H,Cl],[ZA134;H,H,Br,H,Cl],[ZA135;H,H,CN,H,Cl],[ZA136;H,H,Ph,H,Cl],[ZA137;H,H,OPh,H,Cl],[ZA138;H,H,c-Pr,H,Cl],[ZA139;H,H,c-Pen,H,Cl],[ZA140;H,H,c-Hex,H,Cl],[ZA141;H,H,H,H,Me],[ZA142;Me,H,H,H,Me],[ZA143;F,H,H,H,Me],[ZA144;Cl,H,H,H,Me],[ZA145;H,Me,H,H,Me],[ZA146;H,Et,H,H,Me],[ZA147;H,Pr,H,H,Me],[ZA148;H,i-Pr,H,H,Me],[ZA149;H,t-Bu,H,H,Me],[ZA150;H,OMe,H,H,Me],[ZA151;H,OEt,H,H,Me],[ZA152;H,OPr,H,H,Me],[ZA153;H,Oi-Pr,H,H,Me],[ZA154;H,CF3,H,H,Me],[ZA155;H,CF2H,H,H,Me],[ZA156;H,CFH2,H,H,Me],[ZA157;H,F,H,H,Me],[ZA158;H,Cl,H,H,Me],[ZA159;H,Br,H,H,Me],[ZA160;H,CN,H,H,Me],[ZA161;H,Ph,H,H,Me],[ZA162;H,OPh,H,H,Me],[ZA163;H,c-Pr,H,H,Me],[ZA164;H,c-Pen,H,H,Me],[ZA165;H,c-Hex,H,H,Me],[ZA166;H,H,Me,H,Me],[ZA167;H,H,Et,H,Me],[ZA168;H,H,Pr,H,Me],[ZA169;H,H,i-Pr,H,Me],[ZA170;H,H,t-Bu,H,Me],[ZA171;H,H,OMe,H,Me],[ZA172;H,H,OEt,H,Me],[ZA173;H,H,OPr,H,Me],[ZA174;H,H,Oi-Pr,H,Me],[ZA175;H,H,CF3,H,Me],[ZA176;H,H,CF2H,H,Me],[ZA177;H,H,CFH2,H,Me],[ZA178;H,H,F,H,Me],[ZA179;H,H,Cl,H,Me],[ZA180;H,H,Br,H,Me],[ZA181;H,H,CN,H,Me],[ZA182;H,H,Ph,H,Me],[ZA183;H,H,OPh,H,Me],[ZA184;H,H,c-Pr,H,Me],[ZA185;H,H,c-Pen,H,Me],[ZA186;H,H,c-Hex,H,Me],[ZA187;H,H,H,H,OMe],[ZA188;Me,H,H,H,OMe],[ZA189;F,H,H,H,OMe],[ZA190;Cl,H,H,H,OMe],[ZA191;H,Me,H,H,OMe],[ZA192;H,Et,H,H,OMe],[ZA193;H,Pr,H,H,OMe],[ZA194;H,i-Pr,H,H,OMe],[ZA195;H,t-Bu,H,H,OMe],[ZA196;H,OMe,H,H,OMe],[ZA197;H,OEt,H,H,OMe],[ZA198;H,OPr,H,H,OMe],[ZA199;H,Oi-Pr,H,H,OMe],[ZA200;H,CF3,H,H,OMe];

[0157] [ZA201;H,CF2H,H,H,OMe],[ZA202;H,CFH2,H,H,OMe],[ZA203;H,F,H,H,OMe],[ZA204;H,Cl,H,H,OMe],[ZA205;H,Br,H,H,OMe],[ZA206;H,CN,H,H,OMe],[ZA207;H,Ph,H,H,OMe],[ZA208;H,OPh,H,H,OMe],[ZA209;H,c-Pr,H,H,OMe],[ZA210;H,c-Pen,H,H,OMe],[ZA211;H,c-Hex,H,H,OMe],[ZA212;H,H,Me,H,OMe],[ZA213;H,H,Et,H,OMe],[ZA214;H,H,Pr,H,OMe],[ZA215;H,H,i-Pr,H,OMe],[ZA216;H,H,t-Bu,H,OMe],[ZA217;H,H,OMe,H,OMe],[ZA218;H,H,OEt,H,OMe],[ZA219;H,H,OPr,H,OMe],[ZA220;H,H,Oi-Pr,H,OMe],[ZA221;H,H,CF3,H,OMe],[ZA222;H,H,CF2H,H,OMe],[ZA223;H,H,CFH2,H,OMe],[ZA224;H,H,F,H,OMe],[ZA225;H,H,Cl,H,OMe],[ZA226;H,H,Br,H,OMe],[ZA227;H,H,CN,H,OMe],[ZA228;H,H,Ph,H,OMe],[ZA229;H,H,OPh,H,OMe],[ZA230;H,H,c-Pr,H,OMe],[ZA231;H,H,c-Pen,H,OMe],[ZA232;H,H,c-Hex,H,OMe],[ZA233;H,H,H,H,CF3],[ZA234;Me,H,H,H,CF3],[ZA235;F,H,H,H,CF3],[ZA236;Cl,H,H,H,CF3],[ZA237;H,Me,H,H,CF3],[ZA238;H,Et,H,H,CF3],[ZA239;H,Pr,H,H,CF3],[ZA240;H,i-Pr,H,H,CF3],[ZA241;H,t-Bu,H,H,CF3],[ZA242;H,OMe,H,H,CF3],[ZA243;H,OEt,H,H,CF3],[ZA244;H,OPr,H,H,CF3],[ZA245;H,Oi-Pr,H,H,CF3],[ZA246;H,CF3,H,H,CF3],[ZA247;H,CF2H,H,H,CF3],[ZA248;H,CFH2,H,H,CF3],[ZA249;H,F,H,H,CF3],[ZA250;H,Cl,H,H,CF3],[ZA251;H,Br,H,H,CF3],[ZA252;H,CN,H,H,CF3],[ZA253;H,Ph,H,H,CF3],[ZA254;H,OPh,H,H,CF3],[ZA255;H,c-Pr,H,H,CF3],[ZA256;H,c-Pen,H,H,CF3],[ZA257;H,c-Hex,H,H,CF3],[ZA258;H,H,Me,H,CF3],[ZA259;H,H,Et,H,CF3],[ZA260;H,H,Pr,H,CF3],[ZA261;H,H,i-Pr,H,CF3],[ZA262;H,H,t-Bu,H,CF3],[ZA263;H,H,OMe,H,CF3],[ZA264;H,H,OEt,H,CF3],[ZA265;H,H,OPr,H,CF3],[ZA266;H,H,Oi-Pr,H,CF3],[ZA267;H,H,CF3,H,CF3],[ZA268;H,H,CF2H,H,CF3],[ZA269;H,H,CFH2,H,CF3],[ZA270;H,H,F,H,CF3],[ZA271;H,H,Cl,H,CF3],[ZA272;H,H,Br,H,CF3],[ZA273;H,H,CN,H,CF3],[ZA274;H,H,Ph,H,CF3],[ZA275;H,H,OPh,H,CF3],[ZA276;H,H,c-Pr,H,CF3],[ZA277;H,H,c-Pen,H,CF3],[ZA278;H,H,c-Hex,H,CF3],[ZA279;H,F,F,H,H],[ZA280;H,F,H,F,H],[ZA281;H,F,F,F,H],[ZA282;F,F,F,H,H],[ZA283;F,F,H,F,H],[ZA284;F,H,F,H,F],[ZA285;F,F,F,F,F],[ZA286;H,Cl,H,Cl,H],[ZA287;H,OMe,H,OMe,H],[ZA288;H,F,Cl,H,H],[ZA289;H,F,Me,H,H],[ZA290;H,F,OMe,H,H],[ZA291;H,F,CF3,H,H],[ZA292;H,Cl,F,H,H],[ZA293;H,Cl,Cl,H,H],[ZA294;H,Cl,Me,H,H],[ZA295;H,Cl,OMe,H,H],[ZA296;H,Cl,CF3,H,H],[ZA 297;H,Me,F,H,H],[ZA298;H,Me,Cl,H,H],[ZA299;H,Me,Me,H,H],[ZA300;H,Me,OMe,H,H],;

[0158] [ZA301;H,Me,CF3,H,H],[ZA302;H,OMe,F,H,H],[ZA303;H,OMe,Cl,H,H],[ZA304;H,OMe,Me,H,H],[ZA305;H,OMe,OMe,H,H],[ZA306;H, OMe,CF3,H,H],[ZA307;H,CF3,F,H,H],[ZA308;H,CF3,Cl,H,H],[ZA309;H,CF3,F,H,H],[ZA310;H,CF3,Cl,H,H],[ZA311;H,CF3,F,H,H]

[0159] In the compound represented by formula (1B), R 1 is a chlorine atom, L is an oxygen atom, m is 1, and R X2 , R X3 , R X4 , R X5 and R X6 Compounds in which the above is any of the combinations described in Combination A (hereinafter, referred to as compound group SX6).

[0160] In the compound represented by formula (1B), R 1 is a methyl group, L is CH2, m is 1, and R X2 , R X3 , R X4 , R X5 and R X6 Compounds in which the above is any of the combinations described in Combination A (hereinafter referred to as compound group SX7).

[0161] In the compound represented by formula (1B), R 1 is a chlorine atom, L is CH2, m is 1, and R X2 , R X3 , R X4 , R X5and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX8).

[0162] In the compound represented by formula (1B), R 1 is a methyl group, L is an oxygen atom, m is 2, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX9).

[0163] In the compound represented by formula (1B), R 1 is a chlorine atom, L is an oxygen atom, m is 2, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX10).

[0164] In the compound represented by formula (1B), R 1 is a methyl group, L is CH2, m is 2, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX11).

[0165] In the compound represented by formula (1B), R 1 is a chlorine atom, L is CH2, m is 2, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX12).

[0166] In the compound represented by formula (1B), R 1 is a methyl group, L is an oxygen atom, m is 3, and RX2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX13).

[0167] In the compound represented by formula (1B), R 1 is a chlorine atom, L is an oxygen atom, m is 3, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX14).

[0168] In the compound represented by formula (1B), R 1 is a methyl group, L is CH2, m is 3, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX15).

[0169] In the compound represented by formula (1B), R 1 is a chlorine atom, L is CH2, m is 3, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX16).

[0170] Formula (1C): [ka] [wherein G represents any one of the formulae G1 to G28. [ka] [ka] [ka] 〕 In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, m is 1, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 and is any one of the combinations described in Combination B (hereinafter referred to as compound group SX17).

[0171] Combination B consists of substituent numbers ZB1 to ZB1145. The substituent numbers ZB1 to ZB1145 refer to the structures of G and the substituents R corresponding to the structures of G in the compound represented by formula (1C), the compound represented by formula (2C), and the compound represented by formula (3C). X7 , R X8 , R X9 and R X10 The following represents a combination of [substituent number; G, R X7 ,R X8 ,R X9 ,R X10 For example, the substituent number ZB2 is G1, and R X7 is a methyl group, and R X8 , R X9 and R X10 is a hydrogen atom.

[0172] Combination B [ZB1;G1,H,H,H,H],[ZB2;G1,Me,H,H,H],[ZB3;G1,Et,H,H,H],[ZB4;G1,Pr,H,H,H],[ZB5;G1,i-Pr,H,H,H],[ZB6;G1,c-Pr,H,H,H],[ZB7;G1,Ph,H,H,H],[ZB8;G1,OMe,H,H,H],[ZB9;G1,OEt,H,H,H],[ZB10;G1,OPh,H,H,H],[ZB11;G1,CF3,H,H,H],[ZB12;G1,F,H,H,H],[ZB13;G1,Cl,H,H,H],[ZB14;G1,Br,H,H,H],[ZB15;G1,CN,H,H,H],[ZB16;G1,H,Me,H,H],[ZB17;G1,H,Et,H,H],[ZB18;G1,H,Pr,H,H],[ZB19;G1,H,i-Pr,H,H],[ZB20;G1,H,c-Pr,H,H],[ZB21;G1,H,Ph,H,H],[ZB22;G1,H,OMe,H,H],[ZB23;G1,H,OEt,H,H],[ZB24;G1,H,OPh,H,H],[ZB25;G1,H,CF3,H,H],[ZB26;G1,H,F,H,H],[ZB27;G1,H,Cl,H,H],[ZB28;G1,H,Br,H,H],[ZB29;G1,H,CN,H,H],[ZB30;G1,H,H,Me,H],[ZB31;G1,H,H,Et,H],[ZB32;G1,H,H,Pr,H],[ZB33;G1,H,H,i-Pr,H],[ZB34;G1,H,H,c-Pr,H],[ZB35;G1,H,H,Ph,H],[ZB36;G1,H,H,OMe,H],[ZB37;G1,H,H,OEt,H],[ZB38;G1,H,H,OPh,H],[ZB39;G1,H,H,CF3,H],[ZB40;G1,H,H,F,H],[ZB41;G1,H,H,Cl,H],[ZB42;G1,H,H,Br,H],[ZB43;G1,H,H,CN,H],[ZB44;G1,H,H,H,Me],[ZB45;G1,H,H,H,Et],[ZB46;G1,H,H,H,Pr],[ZB47;G1,H,H,H,i-Pr],[ZB48;G1,H,H,H,c-Pr],[ZB49;G1,H,H,H,Ph],[ZB50;G1,H,H,H,OMe],[ZB51;G1,H,H,H,OEt],[ZB52;G1,H,H,H,OPh],[ZB53;G1,H,H,H,CF3],[ZB54;G1,H,H,H,F],[ZB55;G1,H,H,H,Cl],[ZB56;G1,H,H,H,Br],[ZB57;G1,H,H,H,CN],[ZB58;G2,H,H,H,H],[ZB59;G2,Me,H,H,H],[ZB60;G2,Et,H,H,H],[ZB61;G2,Pr,H,H,H],[ZB62;G2,i-Pr,H,H,H],[ZB63;G2,c-Pr,H,H,H],[ZB64;G2,Ph,H,H,H],[ZB65;G2,OMe,H,H,H],[ZB66;G2,OEt,H,H,H],[ZB67;G2,OPh,H,H,H],[ZB68;G2,CF3,H,H,H],[ZB69;G2,F,H,H,H],[ZB70;G2,Cl,H,H,H],[ZB71;G2,Br,H,H,H],[ZB72;G2,CN,H,H,H],[ZB73;G2,H,Me,H,H],[ZB74;G2,H,Et,H,H],[ZB75;G2,H,Pr,H,H],[ZB76;G2,H,i-Pr,H,H],[ZB77;G2,H,c-Pr,H,H],[ZB78;G2,H,Ph,H,H],[ZB79;G2,H,OMe,H,H],[ZB80;G2,H,OEt,H,H],[ZB81;G2,H,OPh,H,H],[ZB82;G2,H,CF3,H,H],[ZB83;G2,H,F,H,H],[ZB84;G2,H,Cl,H,H],[ZB85;G2,H,Br,H,H],[ZB86;G2,H,CN,H,H],[ZB87;G2,H,H,Me,H],[ZB88;G2,H,H,Et,H],[ZB89;G2,H,H,Pr,H],[ZB90;G2,H,H,i-Pr,H],[ZB91;G2,H,H,c-Pr,H],[ZB92;G2,H,H,Ph,H],[ZB93;G2,H,H,OMe,H],[ZB94;G2,H,H,OEt,H],[ZB95;G2,H,H,OPh,H],[ZB96;G2,H,H,CF3,H],[ZB97;G2,H,H,F,H],[ZB98;G2,H,H,Cl,H],[ZB99;G2,H,H,Br,H],[ZB100;G2,H,H,CN,H];

[0173] [ZB101;G2,H,H,H,Me],[ZB102;G2,H,H,H,Et],[ZB103;G2,H,H,H,Pr],[ ZB104;G2,H,H,H,i-Pr],[ZB105;G2,H,H,H,c-Pr],[ZB106;G2,H,H,H,Ph] ,[ZB107;G2,H,H,H,OMe],[ZB108;G2,H,H,H,OEt],[ZB109;G2,H,H,H,OPh ],[ZB110;G2,H,H,H,CF3],[ZB111;G2,H,H,H,F],[ZB112;G2,H,H,H,Cl], [ZB113;G2,H,H,H,Br],[ZB114;G2,H,H,H,CN],[ZB115;G3,H,H,H,H],[ZB 116;G3,Me,H,H,H],[ZB117;G3,Et,H,H,H],[ZB118;G3,Pr,H,H,H],[ZB11 9;G3,i-Pr,H,H,H],[ZB120;G3,c-Pr,H,H,H],[ZB121;G3,Ph,H,H,H],[ZB 122;G3,OMe,H,H,H],[ZB123;G3,OEt,H,H,H],[ZB124;G3,OPh,H,H,H],[Z B125;G3,CF3,H,H,H],[ZB126;G3,F,H,H,H],[ZB127;G3,Cl,H,H,H],[ZB1 28;G3,Br,H,H,H],[ZB129;G3,CN,H,H,H],[ZB130;G3,H,Me,H,H],[ZB131 ;G3,H,Et,H,H],[ZB132;G3,H,Pr,H,H],[ZB133;G3,H,i-Pr,H,H],[ZB134 ;G3,H,c-Pr,H,H],[ZB135;G3,H,Ph,H,H],[ZB136;G3,H,OMe,H,H],[ZB13 7;G3,H,OEt,H,H],[ZB138;G3,H,OPh,H,H],[ZB139;G3,H,CF3,H,H],[ZB1 40;G3,H,F,H,H],[ZB141;G3,H,Cl,H,H],[ZB142;G3,H,Br,H,H],[ZB143; G3,H,CN,H,H],[ZB144;G3,H,H,Me,H],[ZB145;G3,H,H,Et,H],[ZB146;G3 ,H,H,Pr,H],[ZB147;G3,H,H,i-Pr,H],[ZB148;G3,H,H,c-Pr,H],[ZB149;G3,H,H,Ph,H],[ZB150;G3,H,H,OMe,H],[ZB151;G3,H,H,OEt,H],[ZB152 ;G3,H,H,OPh,H],[ZB153;G3,H,H,CF3,H],[ZB154;G3,H,H,F,H],[ZB155; G3,H,H,Cl,H],[ZB156;G3,H,H,Br,H],[ZB157;G3,H,H,CN,H],[ZB158;G 3,H,H,H,Me],[ZB159;G3,H,H,H,Et],[ZB160;G3,H,H,H,Pr],[ZB161;G3, H,H,H,i-Pr],[ZB162;G3,H,H,H,c-Pr],[ZB163;G3,H,H,H,Ph],[ZB164; G3,H,H,H,OMe],[ZB165;G3,H,H,H,OEt],[ZB166;G3,H,H,H,OPh],[ZB167 ;G3,H,H,H,CF3],[ZB168;G3,H,H,H,F],[ZB169;G3,H,H,H,Cl],[ZB170; G3,H,H,H,Br],[ZB171;G3,H,H,H,CN],[ZB172;G4,H,H,H,-],[ZB173;G4, Me,H,H,-],[ZB174;G4,Et,H,H,-],[ZB175;G4,Pr,H,H,-],[ZB176;G4,i -Pr,H,H,-],[ZB177;G4,c-Pr,H,H,-],[ZB178;G4,Ph,H,H,-],[ZB179;G4 ,OMe,H,H,-],[ZB180;G4,OEt,H,H,-],[ZB181;G4,OPh,H,H,-],[ZB182; G4,CF3,H,H,-],[ZB183;G4,F,H,H,-],[ZB184;G4,Cl,H,H,-],[ZB185;G4 ,Br,H,H,-],[ZB186;G4,CN,H,H,-],[ZB187;G4,H,Me,H,-],[ZB188;G4, H,Et,H,-],[ZB189;G4,H,Pr,H,-],[ZB190;G4,H,i-Pr,H,-],[ZB191;G4, H,c-Pr,H,-],[ZB192;G4,H,Ph,H,-],[ZB193;G4,H,OMe,H,-],[ZB194;G 4,H,OEt,H,-],[ZB195;G4,H,OPh,H,-],[ZB196;G4,H,CF3,H,-],[ZB197;G4,H,F,H,-],[ZB198;G4,H,Cl,H,-],[ZB199;G4,H,Br,H,-],[ZB200;G4,H,CN,H,-];

[0174] [ZB201;G4,H,H,Me,-],[ZB202;G4,H,H,Et,-],[ZB203;G4,H,H,Pr,-],[ ZB204;G4,H,H,i-Pr,-],[ZB205;G4,H,H,c-Pr,-],[ZB206;G4,H,H,Ph,-] ,[ZB207;G4,H,H,OMe,-],[ZB208;G4,H,H,OEt,-],[ZB209;G4,H,H,OPh,- ],[ZB210;G4,H,H,CF3,-],[ZB211;G4,H,H,F,-],[ZB212;G4,H,H,Cl,-], [ZB213;G4,H,H,Br,-],[ZB214;G4,H,H,CN,-],[ZB215;G5,H,H,H,-],[ZB 216;G5,Me,H,H,-],[ZB217;G5,Et,H,H,-],[ZB218;G5,Pr,H,H,-],[ZB21 9;G5,i-Pr,H,H,-],[ZB220;G5,c-Pr,H,H,-],[ZB221;G5,Ph,H,H,-],[ZB 222;G5,OMe,H,H,-],[ZB223;G5,OEt,H,H,-],[ZB224;G5,OPh,H,H,-],[Z B225;G5,CF3,H,H,-],[ZB226;G5,F,H,H,-],[ZB227;G5,Cl,H,H,-],[ZB2 28;G5,Br,H,H,-],[ZB229;G5,CN,H,H,-],[ZB230;G5,H,Me,H,-],[ZB231 ;G5,H,Et,H,-],[ZB232;G5,H,Pr,H,-],[ZB233;G5,H,i-Pr,H,-],[ZB234 ;G5,H,c-Pr,H,-],[ZB235;G5,H,Ph,H,-],[ZB236;G5,H,OMe,H,-],[ZB23 7;G5,H,OEt,H,-],[ZB238;G5,H,OPh,H,-],[ZB239;G5,H,CF3,H,-],[ZB2 40;G5,H,F,H,-],[ZB241;G5,H,Cl,H,-],[ZB242;G5,H,Br,H,-],[ZB243; G5,H,CN,H,-],[ZB244;G5,H,H,Me,-],[ZB245;G5,H,H,Et,-],[ZB246;G5 ,H,H,Pr,-],[ZB247;G5,H,H,i-Pr,-],[ZB248;G5,H,H,c-Pr,-],[ZB249;G5,H,H,Ph,-],[ZB250;G5,H,H,OMe,-],[ZB251;G5,H,H,OEt,-],[ZB252;G5,H,H,OPh,-],[ZB253;G5,H,H,CF3,-],[ZB254;G5,H,H,F,-],[ZB255;G5,H,H,Cl,-],[ZB256;G5,H,H,Br,-],[ZB257;G5,H,H,CN,-],[ZB258;G6,H,H,H,-],[ZB259;G6,Me,H,H,-],[ZB260;G6,Et,H,H,-],[ZB261;G6,Pr,H,H,-],[ZB262;G6,i-Pr,H,H,-],[ZB263;G6,c-Pr,H,H,-],[ZB264;G6,Ph,H,H,-],[ZB265;G6,OMe,H,H,-],[ZB266;G6,OEt,H,H,-],[ZB267;G6,OPh,H,H,-],[ZB268;G6,CF3,H,H,-],[ZB269;G6,F,H,H,-],[ZB270;G6,Cl,H,H,-],[ZB271;G6,Br,H,H,-],[ZB272;G6,CN,H,H,-],[ZB273;G6,H,Me,H,-],[ZB274;G6,H,Et,H,-],[ZB275;G6,H,Pr,H,-],[ZB276;G6,H,i-Pr,H,-],[ZB277;G6,H,c-Pr,H,-],[ZB278;G6,H,Ph,H,-],[ZB279;G6,H,OMe,H,-],[ZB280;G6,H,OEt,H,-],[ZB281;G6,H,OPh,H,-],[ZB282;G6,H,CF3,H,-],[ZB283;G6,H,F,H,-],[ZB284;G6,H,Cl,H,-],[ZB285;G6,H,Br,H,-],[ZB286;G6,H,CN,H,-],[ZB287;G6,H,H,Me,-],[ZB288;G6,H,H,Et,-],[ZB289;G6,H,H,Pr,-],[ZB290;G6,H,H,i-Pr,-],[ZB291;G6,H,H,c-Pr,-],[ZB292;G6,H,H,Ph,-],[ZB293;G6,H,H,OMe,-],[ZB294;G6,H,H,OEt,-],[ZB295;G6,H,H,OPh,-],[ZB296;G6,H,H,CF3,-],[ZB297;G6,H,H,F,-],[ZB298;G6,H,H,Cl,-],[ZB299;G6,H,H,Br,-],[ZB300;G6,H,H,CN,-];

[0175] [ZB301;G7,H,H,H,-],[ZB302;G7,Me,H,H,-],[ZB303;G7,Et,H,H,-],[Z B304;G7,Pr,H,H,-],[ZB305;G7,i-Pr,H,H,-],[ZB306;G7,c-Pr,H,H,-], [ZB307;G7,Ph,H,H,-],[ZB308;G7,OMe,H,H,-],[ZB309;G7,OEt,H,H,-], [ZB310;G7,OPh,H,H,-],[ZB311;G7,CF3,H,H,-],[ZB312;G7,F,H,H,-],[ ZB313;G7,Cl,H,H,-],[ZB314;G7,Br,H,H,-],[ZB315;G7,CN,H,H,-],[Z B316;G7,H,Me,H,-],[ZB317;G7,H,Et,H,-],[ZB318;G7,H,Pr,H,-],[ZB3 19;G7,H,i-Pr,H,-],[ZB320;G7,H,c-Pr,H,-],[ZB321;G7,H,Ph,H,-],[Z B322;G7,H,OMe,H,-],[ZB323;G7,H,OEt,H,-],[ZB324;G7,H,OPh,H,-],[ ZB325;G7,H,CF3,H,-],[ZB326;G7,H,F,H,-],[ZB327;G7,H,Cl,H,-],[Z B328;G7,H,Br,H,-],[ZB329;G7,H,CN,H,-],[ZB330;G7,H,H,Me,-],[ZB3 31;G7,H,H,Et,-],[ZB332;G7,H,H,Pr,-],[ZB333;G7,H,H,i-Pr,-],[ZB3 34;G7,H,H,c-Pr,-],[ZB335;G7,H,H,Ph,-],[ZB336;G7,H,H,OMe,-],[ZB 337;G7,H,H,OEt,-],[ZB338;G7,H,H,OPh,-],[ZB339;G7,H,H,CF3,-],[ ZB340;G7,H,H,F,-],[ZB341;G7,H,H,Cl,-],[ZB342;G7,H,H,Br,-],[ZB3 43;G7,H,H,CN,-],[ZB344;G8,H,H,H,-],[ZB345;G8,Me,H,H,-],[ZB346; G8,Et,H,H,-],[ZB347;G8,Pr,H,H,-],[ZB348;G8,i-Pr,H,H,-],[ZB349;G8,c-Pr,H,H,-],[ZB350;G8,Ph,H,H,-],[ZB351;G8,OMe,H,H,-],[ZB352;G8,OEt,H,H,-],[ZB353;G8,OPh,H,H,-],[ZB354;G8,CF3,H,H,-],[ZB355;G8,F,H,H,-],[ZB356;G8,Cl,H,H,-],[ZB357;G8,Br,H,H,-],[ZB358;G8,CN,H,H,-],[ZB359;G8,H,Me,H,-],[ZB360;G8,H,Et,H,-],[ZB361;G8,H,Pr,H,-],[ZB362;G8,H,i-Pr,H,-],[ZB363;G8,H,c-Pr,H,-],[ZB364;G8,H,Ph,H,-],[ZB365;G8,H,OMe,H,-],[ZB366;G8,H,OEt,H,-],[ZB367;G8,H,OPh,H,-],[ZB368;G8,H,CF3,H,-],[ZB369;G8,H,F,H,-],[ZB370;G8,H,Cl,H,-],[ZB371;G8,H,Br,H,-],[ZB372;G8,H,CN,H,-],[ZB373;G8,H,H,Me,-],[ZB374;G8,H,H,Et,-],[ZB375;G8,H,H,Pr,-],[ZB376;G8,H,H,i-Pr,-],[ZB377;G8,H,H,c-Pr,-],[ZB378;G8,H,H,Ph,-],[ZB379;G8,H,H,OMe,-],[ZB380;G8,H,H,OEt,-],[ZB381;G8,H,H,OPh,-],[ZB382;G8,H,H,CF3,-],[ZB383;G8,H,H,F,-],[ZB384;G8,H,H,Cl,-],[ZB385;G8,H,H,Br,-],[ZB386;G8,H,H,CN,-],[ZB387;G9,H,H,H,-],[ZB388;G9,Me,H,H,-],[ZB389;G9,Et,H,H,-],[ZB390;G9,Pr,H,H,-],[ZB391;G9,i-Pr,H,H,-],[ZB392;G9,c-Pr,H,H,-],[ZB393;G9,Ph,H,H,-],[ZB394;G9,OMe,H,H,-],[ZB395;G9,OEt,H,H,-],[ZB396;G9,OPh,H,H,-],[ZB397;G9,CF3,H,H,-],[ZB398;G9,F,H,H,-],[ZB399;G9,Cl,H,H,-],[ZB400;G9,Br,H,H,-];

[0176] [ZB401;G9,CN,H,H,-],[ZB402;G9,H,Me,H,-],[ZB403;G9,H,Et,H,-],[ZB404;G9,H,Pr,H,-],[ZB405;G9,H,i-Pr,H,-],[ZB406;G9,H,c-Pr,H,-],[ZB407;G9,H,Ph,H,-],[ZB408;G9,H,OMe,H,-],[ZB409;G9,H,OEt,H,-],[ZB410;G9,H,OPh,H,-],[ZB411;G9,H,CF3,H,-],[ZB412;G9,H,F,H,-],[ZB413;G9,H,Cl,H,-],[ZB414;G9,H,Br,H,-],[ZB415;G9,H,CN,H,-],[ZB416;G9,H,H,Me,-],[ZB417;G9,H,H,Et,-],[ZB418;G9,H,H,Pr,-],[ZB419;G9,H,H,i-Pr,-],[ZB420;G9,H,H,c-Pr,-],[ZB421;G9,H,H,Ph,-],[ZB422;G9,H,H,OMe,-],[ZB423;G9,H,H,OEt,-],[ZB424;G9,H,H,OPh,-],[ZB425;G9,H,H,CF3,-],[ZB426;G9,H,H,F,-],[ZB427;G9,H,H,Cl,-],[ZB428;G9,H,H,Br,-],[ZB429;G9,H,H,CN,-],[ZB430;G10,H,H,H,-],[ZB431;G10,Me,H,H,-],[ZB432;G10,Et,H,H,-],[ZB433;G10,Pr,H,H,-],[ZB434;G10,i-Pr,H,H,-],[ZB435;G10,c-Pr,H,H,-],[ZB436;G10,Ph,H,H,-],[ZB437;G10,OMe,H,H,-],[ZB438;G10,OEt,H,H,-],[ZB439;G10,OPh,H,H,-],[ZB440;G10,CF3,H,H,-],[ZB441;G10,F,H,H,-],[ZB442;G10,Cl,H,H,-],[ZB443;G10,Br,H,H,-],[ZB444;G10,CN,H,H,-],[ZB445;G10,H,Me,H,-],[ZB446;G10,H,Et,H,-],[ZB447;G10,H,Pr,H,-],[ZB448;G10,H,i-Pr,H,-],[ZB449;G10,H,c-Pr,H,-],[ZB450;G10,H,Ph,H,-],[ZB451;G10,H,OMe,H,-],[ZB452;G10,H,OEt,H,-],[ZB453;G10,H,OPh,H,-],[ZB454;G10,H,CF3,H,-],[ZB455;G10,H,F,H,-],[ZB456;G10,H,Cl,H,-],[ZB457;G10,H,Br,H,-],[ZB458;G10,H,CN,H,-],[ZB459;G10,H,H,Me,-],[ZB460;G10,H,H,Et,-],[ZB461;G10,H,H,Pr,-],[ZB462;G10,H,H,i-Pr,-],[ZB463;G10,H,H,c-Pr,-],[ZB464;G10,H,H,Ph,-],[ZB465;G10,H,H,OMe,-],[ZB466;G10,H,H,OEt,-],[ZB467;G10,H,H,OPh,-],[ZB468;G10,H,H,CF3,-],[ZB469;G10,H,H,F,-],[ZB470;G10,H,H,Cl,-],[ZB471;G10,H,H,Br,-],[ZB472;G10,H,H,CN,-],[ZB473;G11,H,H,H,-],[ZB474;G11,H,Me,H,-],[ZB475;G11,HEt,H,-],[ZB476;G11,HPr,H,-],[ZB477;G11,Hi-Pr,H,-],[ZB478;G11,Hc-Pr,H,-],[ZB479;G11,HPh,H,-],[ZB480;G11,HOMe,H,-],[ZB481;G11,HOEt,H,-],[ZB482;G11,HOPh,H,-],[ZB483;G11,HCF3,H,-],[ZB484;G11,HF,H,-],[ZB485;G11,HCl,H,-],[ZB486;G11,HBr,H,-],[ZB487;G11,HCN,H,-],[ZB488;G11,H,H,Me,-],[ZB489;G11,H,H,Et,-],[ZB490;G11,H,H,Pr,-],[ZB491;G11,H,H,i-Pr,-],[ZB492;G11,H,H,c-Pr,-],[ZB493;G11,H,H,Ph,-],[ZB494;G11,H,H,OMe,-],[ZB495;G11,H,H,OEt,-],[ZB496;G11,H,H,OPh,-],[ZB497;G11,H,H,CF3,-],[ZB498;G11,H,H,F,-],[ZB499;G11,H,H,Cl,-],[ZB500;G11,H,H,Br,-];

[0177] [ZB501;G11,H,H,CN,-],[ZB502;G11,Me,H,H,-],[ZB503;G11,Me,Me,H,-],[ZB504;G11,MeEt,H,-],[ZB505;G11,MePr,H,-],[ZB506;G11,Mei-Pr,H,-],[ZB507;G11,Mec-Pr,H,-],[ZB508;G11,MePh,H,-],[ZB509;G11,MeOMe,H,-],[ZB510;G11,MeOEt,H,-],[ZB511;G11,MeOPh,H,-],[ZB512;G11,MeCF3,H,-],[ZB513;G11,MeF,H,-],[ZB514;G11,MeCl,H,-],[ZB515;G11,MeBr,H,-],[ZB516;G11,MeCN,H,-],[ZB517;G11,Me,H,Me,-],[ZB518;G11,Me,H,Et,-],[ZB519;G11,Me,H,Pr,-],[ZB520;G11,Me,H,i-Pr,-],[ZB521;G11,Me,H,c-Pr,-],[ZB522;G11,Me,H,Ph,-],[ZB523;G11,Me,H,OMe,-],[ZB524;G11,Me,H,OEt,-],[ZB525;G11,Me,H,OPh,-],[ZB526;G11,Me,H,CF3,-],[ZB527;G11,Me,H,F,-],[ZB528;G11,Me,H,Cl,-],[ZB529;G11,Me,H,Br,-],[ZB530;G11,Me,H,CN,-],[ZB531;G12,H,H,H,-],[ZB532;G12,Me,H,H,-],[ZB533;G12,Et,H,H,-],[ZB534;G12,Pr,H,H,-],[ZB535;G12,i-Pr,H,H,-],[ZB536;G12,c-Pr,H,H,-],[ZB537;G12,Ph,H,H,-],[ZB538;G12,OMe,H,H,-],[ZB539;G12,OEt,H,H,-],[ZB540;G12,OPh,H,H,-],[ZB541;G12,CF3,H,H,-],[ZB542;G12,F,H,H,-],[ZB543;G12,Cl,H,H,-],[ZB544;G12,Br,H,H,-],[ZB545;G12,CN,H,H,-],[ZB546;G12,H,Me,H,-],[ZB547;G12,H,Et,H,-],[ZB548;G12,H,Pr,H,-],[ZB549;G12,H,i-Pr,H,-],[ZB550;G12,H,c-Pr,H,-],[ZB551;G12,H,Ph,H,-],[ZB552;G12,H,OMe,H,-],[ZB553;G12,H,OEt,H,-],[ZB554;G12,H,OPh,H,-],[ZB555;G12,H,CF3,H,-],[ZB556;G12,H,F,H,-],[ZB557;G12,H,Cl,H,-],[ZB558;G12,H,Br,H,-],[ZB559;G12,H,CN,H,-],[ZB560;G12,H,H,Me,-],[ZB561;G12,H,H,Et,-],[ZB562;G12,H,H,Pr,-],[ZB563;G12,H,H,i-Pr,-],[ZB564;G12,H,H,c-Pr,-],[ZB565;G12,H,H,Ph,-],[ZB566;G12,H,H,OMe,-],[ZB567;G12,H,H,OEt,-],[ZB568;G12,H,H,OPh,-],[ZB569;G12,H,H,CF3,-],[ZB570;G12,H,H,F,-],[ZB571;G12,H,H,Cl,-],[ZB572;G12,H,H,Br,-],[ZB573;G12,H,H,CN,-],[ZB574;G13,H,H,H,-],[ZB575;G13,Me,H,H,-],[ZB576;G13,Et,H,H,-],[ZB577;G13,Pr,H,H,-],[ZB578;G13,i-Pr,H,H,-],[ZB579;G13,c-Pr,H,H,-],[ZB580;G13,Ph,H,H,-],[ZB581;G13,OMe,H,H,-],[ZB582;G13,OEt,H,H,-],[ZB583;G13,OPh,H,H,-],[ZB584;G13,CF3,H,H,-],[ZB585;G13,F,H,H,-],[ZB586;G13,Cl,H,H,-],[ZB587;G13,Br,H,H,-],[ZB588;G13,CN,H,H,-],[ZB589;G13,H,H,Me,-],[ZB590;G13,H,H,Et,-],[ZB591;G13,H,H,Pr,-],[ZB592;G13,H,H,i-Pr,-],[ZB593;G13,H,H,c-Pr,-],[ZB594;G13,H,H,Ph,-],[ZB595;G13,H,H,OMe,-],[ZB596;G13,H,H,OEt,-],[ZB597;G13,H,H,OPh,-],[ZB598;G13,H,H,CF3,-],[ZB599;G13,H,H,F,-],[ZB600;G13,H,H,Cl,-];

[0178] [ZB601;G13,H,H,Br,-],[ZB602;G13,H,H,CN,-],[ZB603;G13,H,Me,H,-],[ZB604;G13,Me,Me,H,-],[ZB605;G13,Et,Me,H,-],[ZB606;G13,Pr,Me,H,-],[ZB607;G13,i-Pr,Me,H,-],[ZB608;G13,c-Pr,Me,H,-],[ZB609;G13,Ph,Me,H,-],[ZB610;G13,OMe,Me,H,-],[ZB611;G13,OEt,Me,H,-],[ZB612;G13,OPh,Me,H,-],[ZB613;G13,CF3,Me,H,-],[ZB614;G13,F,Me,H,-],[ZB615;G13,Cl,Me,H,-],[ZB616;G13,Br,Me,H,-],[ZB617;G13,CN,Me,H,-],[ZB618;G13,H,Me,Me,-],[ZB619;G13,H,Me,Et,-],[ZB620;G13,H,Me,Pr,-],[ZB621;G13,H,Me,i-Pr,-],[ZB622;G13,H,Me,c-Pr,-],[ZB623;G13,H,Me,Ph,-],[ZB624;G13,H,Me,OMe,-],[ZB625;G13,H,Me,OEt,-],[ZB626;G13,H,Me,OPh,-],[ZB627;G13,H,Me,CF3,-],[ZB628;G13,H,Me,F,-],[ZB629;G13,H,Me,Cl,-],[ZB630;G13,H,Me,Br,-],[ZB631;G13,H,Me,CN,-],[ZB632;G14,H,H,H,-],[ZB633;G14,Me,H,H,-],[ZB634;G14,Et,H,H,-],[ZB635;G14,Pr,H,H,-],[ZB636;G14,i-Pr,H,H,-],[ZB637;G14,c-Pr,H,H,-],[ZB638;G14,Ph,H,H,-],[ZB639;G14,OMe,H,H,-],[ZB640;G14,OEt,H,H,-],[ZB641;G14,OPh,H,H,-],[ZB642;G14,CF3,H,H,-],[ZB643;G14,F,H,H,-],[ZB644;G14,Cl,H,H,-],[ZB645;G14,Br,H,H,-],[ZB646;G14,CN,H,H,-],[ZB647;G14,H,Me,H,-],[ZB648;G14,H,Et,H,-],[ZB64 9;G14,H,Pr,H,-],[ZB650;G14,H,i-Pr,H,-],[ZB651;G14,H,c-Pr,H,-], [ZB652;G14,H,Ph,H,-],[ZB653;G14,H,OMe,H,-],[ZB654;G14,H,OEt,H ,-],[ZB655;G14,H,OPh,H,-],[ZB656;G14,H,CF3,H,-],[ZB657;G14,H,F ,H,-],[ZB658;G14,H,Cl,H,-],[ZB659;G14,H,Br,H,-],[ZB660;G14,H, CN,H,-],[ZB661;G14,H,H,Me,-],[ZB662;G14,H,H,Et,-],[ZB663;G14,H ,H,Pr,-],[ZB664;G14,H,H,i-Pr,-],[ZB665;G14,H,H,c-Pr,-],[ZB666; G14,H,H,Ph,-],[ZB667;G14,H,H,OMe,-],[ZB668;G14,H,H,OEt,-],[ZB6 69;G14,H,H,OPh,-],[ZB670;G14,H,H,CF3,-],[ZB671;G14,H,H,F,-],[ ZB672;G14,H,H,Cl,-],[ZB673;G14,H,H,Br,-],[ZB674;G14,H,H,CN,-], [ZB675;G15,H,H,H,-],[ZB676;G15,Me,H,H,-],[ZB677;G15,Et,H,H,-] ,[ZB678;G15,Pr,H,H,-],[ZB679;G15,i-Pr,H,H,-],[ZB680;G15,c-Pr,H ,H,-],[ZB681;G15,Ph,H,H,-],[ZB682;G15,OMe,H,H,-],[ZB683;G15,O Et,H,H,-],[ZB684;G15,OPh,H,H,-],[ZB685;G15,CF3,H,H,-],[ZB686;G 15,F,H,H,-],[ZB687;G15,Cl,H,H,-],[ZB688;G15,Br,H,H,-],[ZB689;G 15,CN,H,H,-],[ZB690;G15,H,Me,H,-],[ZB691;G15,H,Et,H,-],[ZB692;G15,H,Pr,H,-],[ZB693;G15,H,i-Pr,H,-],[ZB694;G15,H,c-Pr,H,-],[ZB695;G15,H,Ph,H,-],[ZB696;G15,H,OMe,H,-],[ZB697;G15,H,OEt,H,-],[ZB698;G15,H,OPh,H,-],[ZB699;G15,H,CF3,H,-],[ZB700;G15,H,F,H,-];

[0179] [ZB701;G15,H,Cl,H,-],[ZB702;G15,H,Br,H,-],[ZB703;G15,H,CN,H,-],[ZB704;G15,H,H,Me,-],[ZB705;G15,H,H,Et,-],[ZB706;G15,H,H,Pr,-],[ZB707;G15,H,H,i-Pr,-],[ZB708;G15,H,H,c-Pr,-],[ZB709;G15,H,H,Ph,-],[ZB710;G15,H,H,OMe,-],[ZB711;G15,H,H,OEt,-],[ZB712;G15,H,H,OPh,-],[ZB713;G15,H,H,CF3,-],[ZB714;G15,H,H,F,-],[ZB715;G15,H,H,Cl,-],[ZB716;G15,H,H,Br,-],[ZB717;G15,H,H,CN,-],[ZB718;G16,H,H,-,-],[ZB719;G16,Me,H,-,-],[ZB720;G16,Et,H,-,-],[ZB721;G16,Pr,H,-,-],[ZB722;G16,i-Pr,H,-,-],[ZB723;G16,c-Pr,H,-,-],[ZB724;G16,Ph,H,-,-],[ZB725;G16,OMe,H,-,-],[ZB726;G16,OEt,H,-,-],[ZB727;G16,OPh,H,-,-],[ZB728;G16,CF3,H,-,-],[ZB729;G16,F,H,-,-],[ZB730;G16,Cl,H,-,-],[ZB731;G16,Br,H,-,-],[ZB732;G16,CN,H,-,-],[ZB733;G16,H,Me,-,-],[ZB734;G16,H,Et,-,-],[ZB735;G16,H,Pr,-,-],[ZB736;G16,H,i-Pr,-,-],[ZB737;G16,H,c-Pr,-,-],[ZB738;G16,H,Ph,-,-],[ZB739;G16,H,OMe,-,-],[ZB740;G16,H,OEt,-,-],[ZB741;G16,H,OPh,-,-],[ZB742;G16,H,CF3,-,-],[ZB743;G16,H,F,-,-],[ZB744;G16,H,Cl,-,-],[ZB745;G16,H,Br,-,-],[ZB746;G16,H,CN,-,-],[ZB747;G17,H,H,-,-],[ZB748;G17,Me,H,-,-],[ZB749;G17,Et,H,-,-],[ZB750;G17,Pr,H,-,-],[ZB751;G17,i-Pr,H,-,-],[ZB752;G17,c-Pr,H,-,-],[ZB753;G17,Ph,H,-,-],[ZB754;G17,OMe,H,-,-],[ZB755;G17,OEt,H,-,-],[ZB756;G17,OPh,H,-,-],[ZB757;G17,CF3,H,-,-],[ZB758;G17,F,H,-,-],[ZB759;G17,Cl,H,-,-],[ZB760;G17,Br,H,-,-],[ZB761;G17,CN,H,-,-],[ZB762;G17,H,Me,-,-],[ZB763;G17,H,Et,-,-],[ZB764;G17,H,Pr,-,-],[ZB765;G17,H,i-Pr,-,-],[ZB766;G17,H,c-Pr,-,-],[ZB767;G17,H,Ph,-,-],[ZB768;G17,H,OMe,-,-],[ZB769;G17,H,OEt,-,-],[ZB770;G17,H,OPh,-,-],[ZB771;G17,H,CF3,-,-],[ZB772;G17,H,F,-,-],[ZB773;G17,H,Cl,-,-],[ZB774;G17,H,Br,-,-],[ZB775;G17,H,CN,-,-],[ZB776;G18,H,H,-,-],[ZB777;G18,Me,H,-,-],[ZB778;G18,Et,H,-,-],[ZB779;G18,Pr,H,-,-],[ZB780;G18,i-Pr,H,-,-],[ZB781;G18,c-Pr,H,-,-],[ZB782;G18,Ph,H,-,-],[ZB783;G18,OMe,H,-,-],[ZB784;G18,OEt,H,-,-],[ZB785;G18,OPh,H,-,-],[ZB786;G18,CF3,H,-,-],[ZB787;G18,F,H,-,-],[ZB788;G18,Cl,H,-,-],[ZB789;G18,Br,H,-,-],[ZB790;G18,CN,H,-,-],[ZB791;G18,H,Me,-,-],[ZB792;G18,H,Et,-,-],[ZB793;G18,H,Pr,-,-],[ZB794;G18,H,i-Pr,-,-],[ZB795;G18,H,c-Pr,-,-],[ZB796;G18,H,Ph,-,-],[ZB797;G18,H,OMe,-,-],[ZB798;G18,H,OEt,-,-],[ZB799;G18,H,OPh,-,-],[ZB800;G18,H,CF3,-,-];

[0180] [ZB801;G18,H,F,-,-],[ZB802;G18,H,Cl,-,-],[ZB803;G18,H,Br,-,-],[ZB804;G18,H,CN,-,-],[ZB805;G19,H,H,-,-],[ZB806;G19,Me,H,-,-] . ,H,-,-],[ZB813;G19,OEt,H,-,-],[ZB814;G19,OPh,H,-,-],[ZB815;G19,CF3,H,-,-],[ZB816;G19,F,H,-,-],[ZB817;G19,Cl,H,-,-],[ZB818;G1 9,Br,H,-,-],[ZB819;G19,CN,H,-,-],[ZB820;G19,H,Me,-,-],[ZB821;G19,H,Et,-,-],[ZB822;G19,H,Pr,-,-],[ZB823;G19,H,i-Pr,-,-],[ZB82 4;G19,H,c-Pr,-,-],[ZB825;G19,H,Ph,-,-],[ZB826;G19,H,OMe,-,-],[ZB827;G19,H,OEt,-,-],[ZB828;G19,H,OPh,-,-],[ZB829;G19,H,CF3,-, -],[ZB830;G19,H,F,-,-],[ZB831;G19,H,Cl,-,-],[ZB832;G19,H,Br,-,-],[ZB833;G19,H,CN,-,-],[ZB834;G20,H,H,-,-],[ZB835;G20,Me,H,- -],[ZB836;G20,Et,H,-,-],[ZB837;G20,Pr,H,-,-],[ZB838;G20,i-Pr,H,-,-],[ZB839;G20,c-Pr,H,-,-],[ZB840;G20,Ph,H,-,-],[ZB841;G20,OMe,H,-,-],[ZB842;G20,OEt,H,-,-],[ZB843;G20,OPh,H,-,-],[ZB844;G20,CF3,H,-,-],[ZB845;G20,F,H,-,-],[ZB846;G20,Cl,H,-,-],[ZB847;G20,Br,H,-,-],[ZB848;G20,CN,H,-,-],[ZB849;G20,H,Me,-,-],[ZB850;G20,H,Et,-,-],[ZB851;G20,H,Pr,-,-],[ZB852;G20,H,i-Pr,-,-],[ZB853;G20,H,c-Pr,-,-],[ZB854;G20,H,Ph,-,-],[ZB855;G20,H,OMe,-,-],[ZB856;G20,H,OEt,-,-],[ZB857;G20,H,OPh,-,-],[ZB858;G20,H,CF 3,-,-],[ZB859;G20,H,F,-,-],[ZB860;G20,H,Cl,-,-],[ZB861;G20,H,Br,-,-],[ZB862;G20,H,CN,-,-],[ZB863;G21,H,H,-,-],[ZB864;G21,Me ,H,-,-],[ZB865;G21,Et,H,-,-],[ZB866;G21,Pr,H,-,-],[ZB867;G21,i-Pr,H,-,-],[ZB868;G21,c-Pr,H,-,-],[ZB869;G21,Ph,H,-,-],[ZB870 ;G21,OMe,H,-,-],[ZB871;G21,OEt,H,-,-],[ZB872;G21,OPh,H,-,-],[ZB873;G21,CF3,H,-,-],[ZB874;G21,F,H,-,-],[ZB875;G21,Cl,H,-,-], [ZB876;G21,Br,H,-,-],[ZB877;G21,CN,H,-,-],[ZB878;G21,H,Me,-,-],[ZB879;G21,H,Et,-,-],[ZB880;G21,H,Pr,-,-],[ZB881;G21,H,i-Pr, -,-],[ZB882;G21,H,c-Pr,-,-],[ZB883;G21,H,Ph,-,-],[ZB884;G21,H,OMe,-,-],[ZB885;G21,H,OEt,-,-],[ZB886;G21,H,OPh,-,-],[ZB887;G 21,H,CF3,-,-],[ZB888;G21,H,F,-,-],[ZB889;G21,H,Cl,-,-],[ZB890;G21,H,Br,-,-],[ZB891;G21,H,CN,-,-],[ZB892;G22,H,H,-,-],[ZB893;G22,Me,H,-,-],[ZB894;G22,Et,H,-,-],[ZB895;G22,Pr,H,-,-],[ZB896;G22,i-Pr,H,-,-],[ZB897;G22,c-Pr,H,-,-],[ZB898;G22,Ph,H,-,-],[ZB899;G22,OMe,H,-,-],[ZB900;G22,OEt,H,-,-];

[0181] [ZB901;G22,OPh,H,-,-],[ZB902;G22,CF3,H,-,-],[ZB903;G22,F,H,-,-],[ZB904;G22,Cl,H,-,-],[ZB905;G22,Br,H,-,-],[ZB906;G22,CN,H,-,-],[ZB907;G22,H,Me,-,-],[ZB908;G22,H,Et,-,-],[ZB909;G22,H,Pr,-,-],[ZB910;G22,H,i-Pr,-,-],[ZB911;G22,H,c-Pr,-,-],[ZB912;G22,H,Ph,-,-],[ZB913;G22,H,OMe,-,-],[ZB914;G22,H,OEt,-,-],[ZB915;G22,H,OPh,-,-],[ZB916;G22,H,CF3,-,-],[ZB917;G22,H,F,-,-],[ZB918;G22,H,Cl,-,-],[ZB919;G22,H,Br,-,-],[ZB920;G22,H,CN,-,-],[ZB921;G23,H,H,-,-],[ZB922;G23,Me,H,-,-],[ZB923;G23,Et,H,-,-],[ZB924;G23,Pr,H,-,-],[ZB925;G23,i-Pr,H,-,-],[ZB926;G23,c-Pr,H,-,-],[ZB927;G23,Ph,H,-,-],[ZB928;G23,OMe,H,-,-],[ZB929;G23,OEt,H,-,-],[ZB930;G23,OPh,H,-,-],[ZB931;G23,CF3,H,-,-],[ZB932;G23,F,H,-,-],[ZB933;G23,Cl,H,-,-],[ZB934;G23,Br,H,-,-],[ZB935;G23,CN,H,-,-],[ZB936;G23,H,Me,-,-],[ZB937;G23,H,Et,-,-],[ZB938;G23,H,Pr,-,-],[ZB939;G23,H,i-Pr,-,-],[ZB940;G23,H,c-Pr,-,-],[ZB941;G23,H,Ph,-,-],[ZB942;G23,H,OMe,-,-],[ZB943;G23,H,OEt,-,-],[ZB944;G23,H,OPh,-,-],[ZB945;G23,H,CF3,-,-],[ZB946;G23,H,F,-,-],[ZB947;G23,H,Cl,-,-],[ZB948;G23,H,Br,-,-],[ZB949;G23,H,CN,-,-],[ZB950;G24,H,H,-,-],[ZB951;G24,Me,H,-,-],[ZB952;G24,Et,H,-,-],[ZB953;G24,Pr,H,-,-],[ZB954;G24,i-Pr,H,-,-],[ZB955;G24,c-Pr,H,-,-],[ZB956;G24,Ph,H,-,-],[ZB957;G24,OMe,H,-,-],[ZB958;G24,OEt,H,-,-],[ZB959;G24,OPh,H,-,-],[ZB960;G24,CF3,H,-,-],[ZB961;G24,F,H,-,-],[ZB962;G24,Cl,H,-,-],[ZB963;G24,Br,H,-,-],[ZB964;G24,CN,H,-,-],[ZB965;G24,H,Me,-,-],[ZB966;G24,H,Et,-,-],[ZB967;G24,H,Pr,-,-],[ZB968;G24,H,i-Pr,-,-],[ZB969;G24,H,c-Pr,-,-],[ZB970;G24,H,Ph,-,-],[ZB971;G24,H,OMe,-,-],[ZB972;G24,H,OEt,-,-],[ZB973;G24,H,OPh,-,-],[ZB974;G24,H,CF3,-,-],[ZB975;G24,H,F,-,-],[ZB976;G24,H,Cl,-,-],[ZB977;G24,H,Br,-,-],[ZB978;G24,H,CN,-,-],[ZB979;G25,H,H,H,-],[ZB980;G25,H,Me,H,-],[ZB981;G25,H,Et,H,-],[ZB982;G25,H,Pr,H,-],[ZB983;G25,H,i-Pr,H,-],[ZB984;G25,H,c-Pr,H,-],[ZB985;G25,H,Ph,H,-],[ZB986;G25,H,OMe,H,-],[ZB987;G25,H,OEt,H,-],[ZB988;G25,H,OPh,H,-],[ZB989;G25,H,CF3,H,-],[ZB990;G25,H,F,H,-],[ZB991;G25,H,Cl,H,-],[ZB992;G25,H,Br,H,-],[ZB993;G25,H,CN,H,-],[ZB994;G25,H,H,Me,-],[ZB995;G25,H,H,Et,-],[ZB996;G25,H,H,Pr,-],[ZB997;G25,H,H,i-Pr,-],[ZB998;G25,H,H,c-Pr,-],[ZB999;G25,H,H,Ph,-],[ZB1000;G25,H,H,OMe,-];

[0182] [ZB1001;G25,H,H,OEt,-],[ZB1002;G25,H,H,OPh,-],[ZB1003;G25,H,H,CF3,-],[ZB1004;G25,H,H,F,-],[ZB1005;G25,H,H,Cl,-],[ZB1006;G25,H,H,Br,-],[ZB1007;G25,H,H,CN,-],[ZB1008;G25,Me,H,H,-],[ZB1009;G25,Me,Me,H,-],[ZB1010;G25,Me,Et,H,-],[ZB1011;G25,Me,Pr,H,-],[ZB1012;G25,Me,i-Pr,H,-],[ZB1013;G25,Me,c-Pr,H,-],[ZB1014;G25,Me,Ph,H,-],[ZB1015;G25,Me,OMe,H,-],[ZB1016;G25,Me,OEt,H,-],[ZB1017;G25,Me,OPh,H,-],[ZB1018;G25,Me,CF3,H,-],[ZB1019;G25,Me,F,H,-],[ZB1020;G25,Me,Cl,H,-],[ZB1021;G25,Me,Br,H,-],[ZB1022;G25,Me,CN,H,-],[ZB1023;G25,Me,H,Me,-],[ZB1024;G25,Me,H,Et,-],[ZB1025;G25,Me,H,Pr,-],[ZB1026;G25,Me,H,i-Pr,-],[ZB1027;G25,Me,H,c-Pr,-],[ZB1028;G25,Me,H,Ph,-],[ZB1029;G25,Me,H,OMe,-],[ZB1030;G25,Me,H,OEt,-],[ZB1031;G25,Me,H,OPh,-],[ZB1032;G25,Me,H,CF3,-],[ZB1033;G25,Me,H,F,-],[ZB1034;G25,Me,H,Cl,-],[ZB1035;G25,Me,H,Br,-],[ZB1036;G25,Me,H,CN,-],[ZB1037;G26,H,H,H,-],[ZB1038;G26,H,Me,H,-],[ZB1039;G26,H,Et,H,-],[ZB1040;G26,H,Pr,H,-],[ZB1041;G26,H,i-Pr,H,-],[ZB1042;G26,H,c-Pr,H,-],[ZB1043;G26,H,Ph,H,-],[ZB1044;G26,H,OMe,H,-],[ZB1045;G26,H,OEt,H,-],[ZB1046;G26,H,OPh,H,-],[ZB1047;G26,H,CF3,H,-],[ZB1048;G26,H,F,H,-],[ZB1049;G26,H,Cl,H,-],[ZB1050;G26,H,Br,H,-],[ZB1051;G26,H,CN,H,-],[ZB1052;G26,H,H,Me,-],[ZB1053;G26,H,H,Et,-],[ZB1054;G26,H,H,Pr,-],[ZB1055;G26,H,H,i-Pr,-],[ZB1056;G26,H,H,c-Pr,-],[ZB1057;G26,H,H,Ph,-],[ZB1058;G26,H,H,OMe,-],[ZB1059;G26,H,H,OEt,-],[ZB1060;G26,H,H,OPh,-],[ZB1061;G26,H,H,CF3,-],[ZB1062;G26,H,H,F,-],[ZB1063;G26,H,H,Cl,-],[ZB1064;G26,H,H,Br,-],[ZB1065;G26,H,H,CN,-],[ZB1066;G26,Me,H,H,-],[ZB1067;G26,Me,Me,H,-],[ZB1068;G26,Me,Et,H,-],[ZB1069;G26,Me,Pr,H,-],[ZB1070;G26,Me,i-Pr,H,-],[ZB1071;G26,Me,c-Pr,H,-],[ZB1072;G26,Me,Ph,H,-],[ZB1073;G26,Me,OMe,H,-],[ZB1074;G26,Me,OEt,H,-],[ZB1075;G26,Me,OPh,H,-],[ZB1076;G26,Me,CF3,H,-],[ZB1077;G26,Me,F,H,-],[ZB1078;G26,Me,Cl,H,-],[ZB1079;G26,Me,Br,H,-],[ZB1080;G26,Me,CN,H,-],[ZB1081;G26,Me,H,Me,-],[ZB1082;G26,Me,H,Et,-],[ZB1083;G26,Me,H,Pr,-],[ZB1084;G26,Me,H,i-Pr,-],[ZB1085;G26,Me,H,c-Pr,-],[ZB1086;G26,Me,H,Ph,-],[ZB1087;G26,Me,H,OMe,-],[ZB1088;G26,Me,H,OEt,-],[ZB1089;G26,Me,H,OPh,-],[ZB1090;G26,Me,H,CF3,-],[ZB1091;G26,Me,H,F,-],[ZB1092;G26,Me,H,Cl,-],[ZB1093;G26,Me,H,Br,-],[ZB1094;G26,Me,H,CN,-],[ZB1095;G27,H,H,H,-],[ZB1096;G27,Me,H,H,-],[ZB1097;G27,Et,H,H,-],[ZB1098;G27,Pr,H,H,-],[ZB1099;G27,i-Pr,H,H,-],[ZB1100;G27,c-Pr,H,H,-];

[0183] [ZB1101;G27,Ph,H,H,-],[ZB1102;G27,OMe,H,H,-],[ZB1103;G27,OEt,H,H,-],[ZB1104;G27,OPh,H,H,-],[ZB1105;G27,CF3,H,H,-],[ZB1106;G27,F,H,H,-],[ZB1107;G27,Cl,H,H,-],[ZB1108;G27,Br,H,H,-],[ZB1109;G27,CN,H,H,-],[ZB1110;G27,H,Me,H,-],[ZB1111;G27,H,Et,H,-],[ZB1112;G27,H,Pr,H,-],[ZB1113;G27,H,i-Pr,H,-],[ZB1114;G27,H,c-Pr,H,-],[ZB1115;G27,H,Ph,H,-],[ZB1116;G27,H,OMe,H,-],[ZB1117;G27,H,OEt,H,-],[ZB1118;G27,H,OPh,H,-],[ZB1119;G27,H,CF3,H,-],[ZB1120;G27,H,F,H,-],[ZB1121;G27,H,Cl,H,-],[ZB1122;G27,H,Br,H,-],[ZB1123;G27,H,CN,H,-],[ZB1124;G27,H,H,Me,-],[ZB1125;G27,H,H,Et,-],[ZB1126;G27,H,H,Pr,-],[ZB1127;G27,H,H,i-Pr,-],[ZB1128;G27,H,H,c-Pr,-],[ZB1129;G27,H,H,Ph,-],[ZB1130;G27,H,H,OMe,-],[ZB1131;G27,H,H,OEt,-],[ZB1132;G27,H,H,OPh,-],[ZB1133;G27,H,H,CF3,-],[ZB1134;G27,H,H,F,-],[ZB1135;G27,H,H,Cl,-],[ZB1136;G27,H,H,Br,-],[ZB1137;G27,H,H,CN,-],[ZB1138;G28,H,H,-,-],[ZB1139;G28,Me,H,-,-],[ZB1140;G28,Cl,H,-,-],[ZB1141;G28,CF3,H,-,-],[ZB1142;G28,H,Me,-,-],[ZB1143;G28,H,Cl,-,-],[ZB1144;G28,H,CF3,-,-],[ZB1145;G28,H,SH,-,-];

[0184] In the compound represented by formula (1C), R 1 is a chlorine atom, L is an oxygen atom, m is 1, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX18).

[0185] In the compound represented by formula (1C), R 1 is a methyl group, L is CH2, m is 1, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX19).

[0186] In the compound represented by formula (1C), R 1 is a chlorine atom, L is CH2, m is 1, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX20).

[0187] In the compound represented by formula (1C), R 1 is a methyl group, L is an oxygen atom, m is 2, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX21).

[0188] In the compound represented by formula (1C), R 1 is a chlorine atom, L is an oxygen atom, m is 2, and the structure of G and the substituent R corresponding to the structure of G X7, R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX22).

[0189] In the compound represented by formula (1C), R 1 is a methyl group, L is CH2, m is 2, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX23).

[0190] In the compound represented by formula (1C), R 1 is a chlorine atom, L is CH2, m is 2, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX24).

[0191] In the compound represented by formula (1C), R 1 is a methyl group, L is an oxygen atom, m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX25).

[0192] In the compound represented by formula (1C), R 1 is a chlorine atom, L is an oxygen atom, m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX26).

[0193] In the compound represented by formula (1C), R 1 is a methyl group, L is CH2, m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX27).

[0194] In the compound represented by formula (1C), R 1 is a chlorine atom, L is CH2, m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any one of the combinations described in Combination B (hereinafter referred to as compound group SX28).

[0195] Formula (1D): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X11 is a substituent selected from Group X, Group Y and Group Z (hereinafter referred to as Compound Group SX29).

[0196] Group Y: A group consisting of Me, Ph, CH2Ph, (CH2)2Ph, (CH2)3Ph, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, and 3-thienyl. Group Z: a ​​group consisting of 1-pyrrolidinyl, 1-piperidinyl, and 4-morpholinyl.

[0197] In the compound represented by formula (1D), R 1 is a chlorine atom, L is an oxygen atom, and R X11 is a substituent selected from Group X, Group Y and Group Z (hereinafter referred to as Compound Group SX30).

[0198] In the compound represented by formula (1D), R 1 is a methyl group, L is CH2, and R X11 is a substituent selected from Group X, Group Y and Group Z (hereinafter referred to as Compound Group SX31).

[0199] In the compound represented by formula (1D), R 1 is a chlorine atom, L is CH2, and R X11 is a substituent selected from Group X, Group Y and Group Z (hereinafter referred to as Compound Group SX32).

[0200] Formula (1E): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X12 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX33).

[0201] In the compound represented by formula (1E), R 1 is a chlorine atom, L is an oxygen atom, and R X12 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX34).

[0202] In the compound represented by formula (1E), R 1 is a methyl group, L is CH2, and R X12 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX35).

[0203] In the compound represented by formula (1E), R 1 is a chlorine atom, L is CH2, and R X12 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX36).

[0204] Formula (1F): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X13 is a hydrogen atom, and R X14 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX37).

[0205] In the compound represented by formula (1F), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is a hydrogen atom, and R X14 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX38).

[0206] In the compound represented by formula (1F), R 1 is a methyl group, L is CH2, and R X13 is a hydrogen atom, and R X14 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX39).

[0207] In the compound represented by formula (1F), R 1 is a chlorine atom, L is CH2, and R X13 is a hydrogen atom, and R X14 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX40).

[0208] In the compound represented by formula (1F), R 1 is a methyl group, L is an oxygen atom, and R X13 is a methyl group, and R X14 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX41).

[0209] In the compound represented by formula (1F), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is a methyl group, and R X14is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX42).

[0210] In the compound represented by formula (1F), R 1 is a methyl group, L is CH2, and R X13 is a methyl group, and R X14 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX43).

[0211] In the compound represented by formula (1F), R 1 is a chlorine atom, L is CH2, and R X13 is a methyl group, and R X14 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX44).

[0212] In the compound represented by formula (1F), R 1 is a methyl group, L is an oxygen atom, and R X13 is an ethyl group, and R X14 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX45).

[0213] In the compound represented by formula (1F), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is an ethyl group, and R X14 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX46).

[0214] In the compound represented by formula (1F), R 1 is a methyl group, L is CH2, and R X13 is an ethyl group, and R X14 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX47).

[0215] In the compound represented by formula (1F), R 1 is a chlorine atom, L is CH2, and R X13is an ethyl group, and R X14 is any one substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX48).

[0216] Formula (1G): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X13 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX49).

[0217] In the compound represented by formula (1G), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX50).

[0218] In the compound represented by formula (1G), R 1 is a methyl group, L is CH2, and R X13 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX51).

[0219] In the compound represented by formula (1G), R 1 is a chlorine atom, L is CH2, and R X13 is a hydrogen atom, and R X2 , R X3 , R X4 , R X5 and RX6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX52).

[0220] In the compound represented by formula (1G), R 1 is a methyl group, L is an oxygen atom, and R X13 is a methyl group, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX53).

[0221] In the compound represented by formula (1G), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is a methyl group, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX54).

[0222] In the compound represented by formula (1G), R 1 is a methyl group, L is CH2, and R X13 is a methyl group, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX55).

[0223] In the compound represented by formula (1G), R 1 is a chlorine atom, L is CH2, and R X13 is a methyl group, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX56).

[0224] In the compound represented by formula (1G), R 1 is a methyl group, L is an oxygen atom, and R X13 is an ethyl group, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX57).

[0225] In the compound represented by formula (1G), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is an ethyl group, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX58).

[0226] In the compound represented by formula (1G), R 1 is a methyl group, L is CH2, and R X13 is an ethyl group, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX59).

[0227] In the compound represented by formula (1G), R 1 is a chlorine atom, L is CH2, and R X13 is an ethyl group, and R X2 , R X3 , R X4 , R X5 and R X6 is any one of the combinations described in Combination A (hereinafter referred to as compound group SX60).

[0228] Formula (1H): [ka] In the compound represented by the formula1 is a methyl group, L is an oxygen atom, and R X15 is a hydrogen atom, and R X16 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX61).

[0229] In the compound represented by formula (1H), R 1 is a chlorine atom, L is an oxygen atom, and R X15 is a hydrogen atom, and R X16 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX62).

[0230] In the compound represented by formula (1H), R 1 is a methyl group, L is CH2, and R X15 is a hydrogen atom, and R X16 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX63).

[0231] In the compound represented by formula (1H), R 1 is a chlorine atom, L is CH2, and R X15 is a hydrogen atom, and R X16 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX64).

[0232] In the compound represented by formula (1H), R 1 is a methyl group, L is an oxygen atom, and R X15 is a methyl group, and R X16 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX65).

[0233] In the compound represented by formula (1H), R 1 is a chlorine atom, L is an oxygen atom, and R X15 is a methyl group, and R X16 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX66).

[0234] In the compound represented by formula (1H), R 1 is a methyl group, L is CH2, and R X15 is a methyl group, and R X16 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX67).

[0235] In the compound represented by formula (1H), R 1 is a chlorine atom, L is CH2, and R X15 is a methyl group, and R X16 Compounds in which is any one of substituents selected from group X and group Y (hereinafter referred to as compound group SX68).

[0236] Formula (1K): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X17 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX69).

[0237] In the compound represented by formula (1K), R 1 is a chlorine atom, L is an oxygen atom, and R X17 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX70).

[0238] In the compound represented by formula (1K), R 1 is a methyl group, L is CH2, and R X17 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX71).

[0239] In the compound represented by formula (1K), R 1 is a chlorine atom, L is CH2, and R X17 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX72).

[0240] Formula (1J): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X18 is a hydrogen atom, and R X19 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX73).

[0241] In the compound represented by formula (1J), R 1 is a chlorine atom, L is an oxygen atom, and R X18 is a hydrogen atom, and R X19 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX74).

[0242] In the compound represented by formula (1J), R 1 is a methyl group, L is CH2, and R X18 is a hydrogen atom, and R X19 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX75).

[0243] In the compound represented by formula (1J), R 1 is a chlorine atom, L is CH2, and R X18 is a hydrogen atom, and R X19 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX76).

[0244] In the compound represented by formula (1J), R 1 is a methyl group, L is an oxygen atom, and R X18 is a methyl group, and R X19 Compounds in which is any one of substituents selected from group X and group Y (hereinafter referred to as compound group SX77).

[0245] In the compound represented by formula (1J), R 1 is a chlorine atom, L is an oxygen atom, and R X18 is a methyl group, and RX19 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX78).

[0246] In the compound represented by formula (1J), R 1 is a methyl group, L is CH2, and R X18 is a methyl group, and R X19 is any one of the substituents selected from Group X and Group Y (hereinafter referred to as Compound Group SX79).

[0247] In the compound represented by formula (1J), R 1 is a chlorine atom, L is CH2, and R X18 is a methyl group, and R X19 is a substituent selected from Group X and Group Y (hereinafter referred to as Compound Group SX80).

[0248] Formula (2A): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X1 is any substituent selected from group X.

[0249] In the compound represented by formula (2A), R 1 is a chlorine atom, L is an oxygen atom, and R X1 is any substituent selected from group X.

[0250] In the compound represented by formula (2A), R 1 is a methyl group, L is CH2, and R X1 is any substituent selected from group X.

[0251] In the compound represented by formula (2A), R 1 is a chlorine atom, L is CH2, and R X1 is any substituent selected from group X.

[0252] Formula (2B): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, m is 1, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0253] In the compound represented by formula (2B), R 1 is a chlorine atom, L is an oxygen atom, m is 1, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0254] In the compound represented by formula (2B), R 1 is a methyl group, L is CH2, m is 1, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0255] In the compound represented by formula (2B), R 1 is a chlorine atom, L is CH2, m is 1, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0256] In the compound represented by formula (2B), R 1 is a methyl group, L is an oxygen atom, m is 2, and R X2 , R X3 , R X4 , R X5 and R X6A compound in which any of the combinations described in Combination A is present.

[0257] In the compound represented by formula (2B), R 1 is a chlorine atom, L is an oxygen atom, m is 2, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0258] In the compound represented by formula (2B), R 1 is a methyl group, L is CH2, m is 2, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0259] In the compound represented by formula (2B), R 1 is a chlorine atom, L is CH2, m is 2, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0260] In the compound represented by formula (2B), R 1 is a methyl group, L is an oxygen atom, m is 3, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0261] In the compound represented by formula (2B), R 1 is a chlorine atom, L is an oxygen atom, m is 3, and R X2 , R X3 , R X4 , R X5 and R X6A compound in which any of the combinations described in Combination A is present.

[0262] In the compound represented by formula (2B), R 1 is a methyl group, L is CH2, m is 3, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0263] In the compound represented by formula (2B), R 1 is a chlorine atom, L is CH2, m is 3, and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0264] Formula (2C): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, m is 1, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 is any of the combinations described in Combination B.

[0265] In the compound represented by formula (2C), R 1 is a chlorine atom, L is an oxygen atom, m is 1, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0266] In the compound represented by formula (2C), R 1 is a methyl group, L is CH2, m is 1, and the structure of G and the substituent R corresponding to the structure of GX7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0267] In the compound represented by formula (2C), R 1 is a chlorine atom, L is CH2, m is 1, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0268] In the compound represented by formula (2C), R 1 is a methyl group, L is an oxygen atom, m is 2, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0269] In the compound represented by formula (2C), R 1 is a chlorine atom, L is an oxygen atom, m is 2, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0270] In the compound represented by formula (2C), R 1 is a methyl group, L is CH2, m is 2, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0271] In the compound represented by formula (2C), R 1 is a chlorine atom, L is CH2, m is 2, and the structure of G and the substituent R corresponding to the structure of G X7, R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0272] In the compound represented by formula (2C), R 1 is a methyl group, L is an oxygen atom, m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0273] In the compound represented by formula (2C), R 1 is a chlorine atom, L is an oxygen atom, m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0274] In the compound represented by formula (2C), R 1 is a methyl group, L is CH2, m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0275] In the compound represented by formula (2C), R 1 is a chlorine atom, L is CH2, m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0276] Formula (2D): [ka] In the compound represented by the formula1 is a methyl group, L is an oxygen atom, and R X11 is a substituent selected from Group X, Group Y and Group Z.

[0277] In the compound represented by formula (2D), R 1 is a chlorine atom, L is an oxygen atom, and R X11 is a substituent selected from Group X, Group Y and Group Z.

[0278] In the compound represented by formula (2D), R 1 is a methyl group, L is CH2, and R X11 is a substituent selected from Group X, Group Y and Group Z.

[0279] In the compound represented by formula (2D), R 1 is a chlorine atom, L is CH2, and R X11 is a substituent selected from Group X, Group Y and Group Z.

[0280] Formula (2F): [ka] In the compound represented by the formula 1 is a methyl group, L is an oxygen atom, and R X13 is a hydrogen atom, and R X14 is a substituent selected from Group X and Group Y.

[0281] In the compound represented by formula (2F), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is a hydrogen atom, and R X14 is a substituent selected from Group X and Group Y.

[0282] In the compound represented by formula (2F), R 1 is a methyl group, L is CH2, and R X13 is a hydrogen atom, and R X14is a substituent selected from Group X and Group Y.

[0283] In the compound represented by formula (2F), R 1 is a chlorine atom, L is CH2, and R X13 is a hydrogen atom, and R X14 is a substituent selected from Group X and Group Y.

[0284] In the compound represented by formula (2F), R 1 is a methyl group, L is an oxygen atom, and R X13 is a methyl group, and R X14 is a substituent selected from Group X and Group Y.

[0285] In the compound represented by formula (2F), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is a methyl group, and R X14 is a substituent selected from Group X and Group Y.

[0286] In the compound represented by formula (2F), R 1 is a methyl group, L is CH2, and R X13 is a methyl group, and R X14 is a substituent selected from Group X and Group Y.

[0287] In the compound represented by formula (2F), R 1 is a chlorine atom, L is CH2, and R X13 is a methyl group, and R X14 is a substituent selected from Group X and Group Y.

[0288] In the compound represented by formula (2F), R 1 is a methyl group, L is an oxygen atom, and R X13 is an ethyl group, and R X14 is a substituent selected from Group X and Group Y.

[0289] In the compound represented by formula (2F), R 1 is a chlorine atom, L is an oxygen atom, and R X13 is an ethyl group, and R X14 is a substituent selected from Group X and Group Y.

[0290] In the compound represented by formula (2F), R 1 is a methyl group, L is CH2, and R X13 is an ethyl group, and R X14 is a substituent selected from Group X and Group Y.

[0291] In the compound represented by formula (2F), R 1 is a chlorine atom, L is CH2, and R X13 is an ethyl group, and R X14 is a substituent selected from Group X and Group Y.

[0292] Formula (3A): [ka] In the compound represented by the formula X1 is any substituent selected from group X.

[0293] Formula (3B): [ka] In the compound represented by the formula: X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0294] In the compound represented by formula (3B), m is 2 and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0295] In the compound represented by formula (3B), m is 3 and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0296] Formula (3C): [ka] In the compound represented by the formula (I), m is 1, and the structure of G and the substituent R corresponding to the structure of G are X7 , R X8 , R X9 and R X10 is any of the combinations described in Combination B.

[0297] In the compound represented by formula (3C), m is 2, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0298] In the compound represented by formula (3C), m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0299] Formula (3D): [ka] In the compound represented by the formula X11 is a substituent selected from Group X, Group Y and Group Z.

[0300] Formula (3F): [ka] In the compound represented by the formula X13 is a hydrogen atom, and R X14 is a substituent selected from Group X and Group Y.

[0301] In the compound represented by formula (3F), R X13 is a methyl group, and R X14 is a substituent selected from Group X and Group Y.

[0302] In the compound represented by formula (3F), R X13 is an ethyl group, and R X14 is a substituent selected from Group X and Group Y.

[0303] Formula (4A): [ka] In the compound represented by the formula: 1 is any substituent selected from group W.

[0304] Group W: A group consisting of Me, Et, Pr, c-Pr, CF3, F, Cl, Br, and I.

[0305] In the compound of formula (4A), L is CH2 and R 1 is any substituent selected from group W.

[0306] Formula (5A) [ka] In the compound represented by the formula X1 is any substituent selected from group X.

[0307] Formula (5B) [ka] In the compound represented by the formula: X2 , RX3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0308] In the compound represented by formula (5B), m is 2 and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0309] In the compound represented by formula (5B), m is 3 and R X2 , R X3 , R X4 , R X5 and R X6 A compound in which any of the combinations described in Combination A is present.

[0310] Formula (5C) [ka] In the compound represented by the formula (I), m is 1, and the structure of G and the substituent R corresponding to the structure of G are X7 , R X8 , R X9 and R X10 is any of the combinations described in Combination B.

[0311] In the compound represented by formula (5C), m is 2, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0312] In the compound represented by formula (5C), m is 3, and the structure of G and the substituent R corresponding to the structure of G X7 , R X8 , R X9 and R X10 A compound in which any of the combinations described in Combination B is present.

[0313] Formula (5D): [ka] In the compound represented by the formula X11 is a substituent selected from Group X, Group Y and Group Z.

[0314] Formula (5F) [ka] In the compound represented by the formula X13 is a hydrogen atom, and R X14 is a substituent selected from Group X and Group Y.

[0315] In the compound represented by formula (5F), R X13 is a methyl group, and R X14 is a substituent selected from Group X and Group Y.

[0316] In the compound represented by formula (5F), R X13 is an ethyl group, and R X14 is a substituent selected from Group X and Group Y.

[0317] Formulation examples of the compound of the present invention are shown below. In addition, parts are parts by weight. Compound S of the present invention represents a compound described in compound group SX1 to SX80.

[0318] Formulation Example 1 A preparation is obtained by thoroughly grinding and mixing 50 parts of any one of the compounds S of the present invention, 3 parts of calcium lignosulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide.

[0319] Formulation Example 2 20 parts of any one of the compounds S of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture is finely pulverized by a wet pulverization method. Then, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and 10 parts of propylene glycol is further added thereto, and the mixture is stirred and mixed to obtain a preparation.

[0320] Formulation Example 3 A preparation is obtained by thoroughly grinding and mixing 2 parts of any one of the present compound S, 88 parts of kaolin clay, and 10 parts of talc.

[0321] Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of any one of the present compound S, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.

[0322] Formulation Example 5 Two parts of any one of the compounds S of the present invention, one part of synthetic hydrous silicon oxide, two parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are thoroughly ground and mixed, and then water is added and the mixture is thoroughly kneaded, granulated, and dried to obtain a formulation.

[0323] Formulation Example 6 20 parts of any one of the present compound S, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1:1), and water are mixed to make a total amount of 100 parts, and the mixture is processed using a pulverizer to obtain a formulation.

[0324] Next, a test example will be shown. The untreated group in Test Examples 1 to 9 refers to a test group conducted under the same conditions as those described in each Test Example, except that DMSO was dispensed instead of the DMSO diluted solution containing the compound of the present invention. In Test Examples 10 to 22, the untreated group refers to a test group in which a water diluted solution of the formulation containing the compound of the present invention was not sprayed.

[0325] Test Example 1: Control test against wheat leaf spot fungus (Septoria tritici) Compounds 1-16, 18-23, 25, 26, 28-30, 33-35, 37, 38-40, 42-52, 54-87, 89, or 90 of the present invention were diluted with DMSO to a concentration of 150 ppm, and 1 μL of the diluted solution was dispensed into a 96-well titer plate. Then, 150 μL of potato decoction liquid medium (PDB medium) preinoculated with spores of the wheat leaf spot fungus was dispensed. The plate was incubated at 18°C ​​for 5 days to allow the wheat leaf spot fungus to grow. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of the wheat leaf spot fungus. The growth rate in the treatments with each compound was 50% or less of that in the untreated control.

[0326] Test Example 2: Control test against soybean anthracnose fungus (Colletotrichum truncatum) Compounds 2-16, 18-20, 25, 26, 29, 38, 40, 42-44, 46-49, 51, 52, 55, 57-64, 71, or 76 of the present invention were diluted with DMSO to a concentration of 150 ppm, and 1 μL of each solution was dispensed into a 96-well titer plate. Then, 150 μL of potato decoction liquid medium (PDB medium) preinoculated with spores of Bacillus subtilis was dispensed. The plates were incubated at 18°C ​​for 4 days to allow growth of Bacillus subtilis. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of Bacillus subtilis. The growth rate in the treatments with each compound was 50% or less of that in the untreated control.

[0327] Test Example 3: Control test against cucurbit gray rot fungus (Phytophthora capsici) Compounds 1-20, 23, 25, 26, 29, 34, 37, 38, 40-49, 51, 52, 54-64, 68, 71, 73-76, 80, 89, or 90 of the present invention were diluted with DMSO to a concentration of 150 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) pre-inoculated with spores of Botrytis cinerea was dispensed. The plate was incubated at 27°C for 3 days to allow growth of Botrytis cinerea. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of Botrytis cinerea. The growth rate in the treatments with each compound was 50% or less of that in the untreated control.

[0328] Test Example 4: Control test against damping-off fungus (Pythium ultimum) Compounds 1-20, 23, 25, 26, 29, 34, 37, 38, 40-49, 51, 52, 54-64, 66, 68, 71-76, 79-81, 84-86, 89, or 90 of the present invention were diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of P. difficile fungus was dispensed. The plate was incubated at 23 °C for 5 days to allow the P. difficile fungus to grow. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of P. difficile fungus. As a result, the growth rate in the treatment zones with each compound was 50% or less of the growth rate in the untreated zone.

[0329] Test Example 5: Control test against corn smut fungus (Ustilago maydis) Compounds 1-20, 23, 25, 26, 29, 30, 34, 37-49, 51, 52, 54-64, 68, 71-76, 78-87, 89, or 90 of the present invention were diluted with DMSO to a concentration of 150 ppm, and 1 μL of each solution was dispensed into a 96-well titer plate. Then, 150 μL of potato decoction liquid medium (PDB medium) pre-inoculated with spores of the common smut fungus was dispensed. The plate was incubated at 18°C ​​for 4 days to allow the common smut fungus to grow. The absorbance at 550 nm in each well of the titer plate was then measured, and this value was used as the growth rate of the common smut fungus. The growth rate in the treatments with each compound was 50% or less of that in the untreated control.

[0330] Test Example 6: Control test against barley scald fungus (Rhynchosporium secalis) Compounds 1-20, 23, 25, 26, 29-49, 51, 52, 54-64, 66-68, 71-87, 89, or 90 of the present invention were diluted with DMSO to a concentration of 150 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) previously inoculated with spores of the barley scald fungus was dispensed. The plate was incubated at 18°C ​​for 7 days to allow the barley scald fungus to grow. The absorbance at 550 nm in each well of the titer plate was then measured, and this value was used as the growth rate of the barley scald fungus. The growth rate in the treatments with each compound was 50% or less of that in the untreated control.

[0331] Test Example 7: Control test against cucumber gray mold fungus (Botrytis cinerea) Compounds 1-20, 23, 25, 26, 29-34, 36-49, 51, 52, 54-64, 66, 68, 71-85, 87, 89, or 90 of the present invention were diluted with DMSO to a concentration of 150 ppm, and 1 μL of the diluted solution was dispensed into a titer plate (96 wells). Then, 150 μL of YB liquid medium inoculated with spores of Botrytis cinerea was dispensed. The plate was incubated at 18°C ​​for 4 days to allow growth of Botrytis cinerea. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of Botrytis cinerea. The growth rate in the treatments with each compound was 50% or less of that in the untreated control.

[0332] Test Example 8: Control test against peach scab fungus (Cladosporium carpophilum) Compounds 1-20, 23, 25, 26, 29-49, 51, 52, 54-64, 66-68, 71-87, 89, or 90 of the present invention were diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells). Then, 150 μL of YB liquid medium previously inoculated with spores of the peach scab fungus was dispensed. The plate was cultured at 18°C ​​for 5 days to allow the peach scab fungus to grow. The absorbance at 550 nm in each well of the titer plate was then measured, and this value was used as the growth rate of the peach scab fungus. As a result, the growth rate in the treatment zones with each compound was 50% or less of the growth rate in the untreated zone.

[0333] Test Example 9: Control test against rice leaf spot fungus (Cochliobolus miyabeanus) Compounds 28, 30-33, 35, 37, 39, 50, 66, 67, 69, 70, 72-75, 77-89, and 90 of the present invention were diluted with DMSO to a concentration of 150 ppm, and 1 μL of the diluted solution was dispensed into a 96-well titer plate. Then, 150 μL of YB liquid medium inoculated with spores of Cochliobolus oryzae was dispensed. The plate was incubated at 23°C for 3 days to allow the Cochliobolus oryzae pathogen to grow. The absorbance at 550 nm in each well of the titer plate was measured, and this value was used as the growth rate of the Cochliobolus oryzae pathogen. The growth rate in the treatments with each compound was 50% or less of that in the untreated control.

[0334] Test Example 10: Control test against soybean rust (Phakopsora pachyrhizi) Leaf discs were prepared by cutting soybean (cultivar: Kurosengoku) leaves to a diameter of 1 cm. 1 mL of agar medium (agar concentration 1.2%) was dispensed into each well of a 24-well microplate, and one leaf disc was placed on the agar medium in each well. 20 μL of a DMSO solution containing 10,000 ppm of the test compound was added to a mixture of 0.5 μL of Sorpol (registered trademark) 1200KX, 4.5 μL of DMSO, and 5 μL of xylene, and mixed. The resulting mixture was diluted with ion-exchanged water to prepare a mixture containing the test compound at the specified concentration. 10 μL of the resulting mixture was sprayed per leaf disc. One day later, a water suspension (1.0 × 10 ) of spores of the soybean rust fungus (Phakopsora pachyrhizi) with the F129L amino acid substitution in the mitochondrial cytochrome b protein was sprayed onto the leaf disc. 5Leaf disks were inoculated by spraying with a solution of 100mg / mL of soybean rust solution. After inoculation, the disks were placed in a climate chamber (lights on for 6 hours, lights off for 18 hours, temperature 23°C, humidity 60%). After one day, the disks were air-dried until all water droplets had disappeared from their surfaces, and then placed again in the climate chamber for 12 days. The lesion area of ​​soybean rust was then examined. As a result, the lesion area of ​​the leaf disks treated with any one of the compounds 1 to 10, 15 to 20, 23, 28 to 31, 33 to 35, 37, 39, 40, 50, 55, 56, 66 to 68, 70, 71 to 87, 89, or 90 of the present invention at a predetermined concentration of 50 ppm was 30% or less of the lesion area of ​​the untreated leaf disks.

[0335] Test Example 11: Control test against rice blast (Pyricularia oryzae) Plastic pots were filled with soil, and rice (cultivar: Hinohikari) was sown therein and cultivated in a greenhouse for 20 days. Compounds 19, 44, and 80 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the foliage of the rice plants so that the mixture adhered well to the leaves. After spraying, the rice plants were air-dried. The sprayed rice plants were then placed in contact with rice seedlings (cultivar: Hinohikari) infected with rice blast fungus at 24°C during the day and 20°C at night under humid conditions for 6 to 7 days, after which the lesion area was examined. The lesion area on the rice plants treated with each compound of the present invention was 30% or less of that on the untreated rice plants.

[0336] Test Example 12: Control test against barley net blotch (Pyrenophora teres) Plastic pots were filled with soil, and barley (variety: Nishinohoshi) was sown and cultivated in a greenhouse for 7 days. Compounds of the present invention (2, 4-6, 13, 14, 16, 18-20, 26, 34, 39, 46-49, 51, 52, 54, 55, 57, 58, 64, 67, 68, 75-77, 80-83, 85-88, or 89), formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the foliage of the barley plants so that sufficient adhesion was achieved. After spraying, the barley plants were air-dried, and one day later, they were inoculated by spraying with an aqueous suspension of spores of the barley net blotch fungus. After inoculation, the barley plants were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 3 days, then cultivated in the greenhouse for 7 days, and the lesion area was then examined. As a result, the lesion area in barley treated with each of the compounds of the present invention was 30% or less of the lesion area in untreated barley.

[0337] Test Example 13: Control test against cucumber downy mildew (Pseudoperonospora cubensis) Plastic pots were filled with soil, and cucumbers (variety: Sagamihanjiro) were sown and grown in a greenhouse for 12 days. Compounds 2, 47, and 61 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the stems and leaves of the cucumbers so that sufficient coverage was achieved on the leaves. After spraying, the cucumbers were air-dried, and one day later, they were inoculated by spraying with a suspension of cucumber downy mildew spores. After inoculation, the cucumbers were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for one day, and then cultivated in the greenhouse for 10 days, after which the lesion area was examined. As a result, the lesion area on cucumbers treated with each compound of the present invention was 30% or less of that on untreated cucumbers.

[0338] Test Example 14: Control test against wheat rust (Puccinia recondita) Plastic pots were filled with soil, and wheat (cultivar: Shirogane) was sown and cultivated in a greenhouse for 9 days. Compounds 2-6, 10-16, 18, 19, 20, 25, 26, 29, 31, 32, 34, 35, 39-42, 46, 47, 49, 52-64, 66-68, 73, 75-78, 80, 81, 83-89, or 90 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the foliage of the wheat so that it adhered well to the leaf surface. After spraying, the wheat was air-dried and cultivated at 20°C under lighting for 5-7 days, after which it was inoculated with wheat rust spores. After inoculation, the wheat was kept at 23°C under dark and humid conditions for 1 day, then cultivated at 20°C under lighting for 8 days, and the lesion area was examined. As a result, the lesion area in the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated wheat.

[0339] Test Example 15: Control test against wheat leaf blight (Septoria tritici) Plastic pots were filled with soil, and wheat (cultivar: Apogee) seeds were sown therein and cultivated in a greenhouse for 10 days. Compounds 1, 3-6, 10, 11, 13-16, 18-21, 25, 26, 29-37, 39, 40, 46-49, 51, 53-55, 57, 58, 64, 72, 73, 75, 77-80, 82, 83, 85-88, or 89 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the foliage of the wheat plants so that the mixture adhered well to the leaves. After spraying, the wheat plants were air-dried, and after 4 days, they were inoculated by spraying with an aqueous suspension containing spores of the wheat leaf spot fungus. After inoculation, the wheat plants were placed under 18°C ​​and high humidity for 3 days, then cultivated under light for 14 to 18 days, after which the lesion area was examined. As a result, the lesion area in the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated wheat.

[0340] Test Example 16: Control test against wheat leaf blight (Septoria tritici) Plastic pots were filled with soil, and wheat (cultivar: Apogee) was sown and grown in a greenhouse for 10 days. A water suspension of spores of Triticum aeruginosa was sprayed onto the pots. After inoculation, the wheat plants were placed under 18°C ​​and high humidity for 3 days. Compounds 3-5, 7-11, 15, 16, 21, 25, 26, 29, 31, 34, 37, 39, 44, 46, 47, 49, 57, 58, 71-75, 77-82, 84, 88, 89, or 90 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the foliage of the wheat plants, ensuring sufficient coverage. After spraying, the wheat plants were air-dried and placed under light for 14 to 18 days, after which the lesion area was assessed. As a result, the lesion area in the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated wheat.

[0341] Test Example 17: Control test against tomato late blight (Phytophthora infestans) Plastic pots were filled with soil, and tomatoes (variety: Patio) were sown and cultivated in a greenhouse for 20 days. Compounds 2, 11-14, 16, 18-21, 29, 35, 39, 49, 51, 52, 55, 56, 60-64, 66, 76, 80, 85, or 86 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the stems and foliage of the tomatoes, ensuring sufficient coverage of the leaves. After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying with an aqueous suspension containing spores of Phytophthora infestans. After inoculation, the tomatoes were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for one day, then cultivated in the greenhouse for four days, after which the lesion area was examined. The lesion area on the tomatoes treated with each compound of the present invention was less than 30% of that on the untreated tomatoes.

[0342] Test Example 18: Control test against soybean rust (Phakopsora pachyrhizi) Soybeans (cultivar: Kurosengoku) were seeded in plastic pots filled with soil and grown in a greenhouse for 10 to 14 days. Compounds 1-16, 18-23, 25, 26, 29-32, 34, 35, 37-40, 44-46, 48, 49, 51-59, 61-64, 68, 71-73, 75-77, 79-83, 85-89, or 90 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the foliage of the soybeans to ensure adequate leaf coverage. After spraying, the soybeans were air-dried, and 2-5 days later, they were inoculated by spraying with an aqueous suspension of soybean rust spores. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 1-2 days, then cultivated in the greenhouse for 12 days, after which the lesion area was examined. As a result, the lesion area in the soybeans treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated soybeans.

[0343] Test Example 19: Control test against soybean rust (Phakopsora pachyrhizi) Soybeans (cultivar: Kurosengoku) were seeded in plastic pots filled with soil and grown in a greenhouse for 10 days. An aqueous suspension containing soybean rust spores was sprayed and inoculated. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 1 day. After cultivation in the greenhouse for 2 days, Compounds 1-16, 18, 19, 21-23, 25, 26, 37, 40, 44, 46, 47-49, 57, 58, 68, 71-77, 80-82, 89, or 90 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the stems and foliage of the soybeans to ensure sufficient coverage of the leaf surface. After spraying, the soybeans were air-dried and grown in a greenhouse for 8 days, after which the lesion area was examined. As a result, the lesion area in the soybeans treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated soybeans.

[0344] Test Example 20: Control test against soybean leaf spot (Cercospora sojina) Soybeans (variety: Tachinagaha) were seeded in plastic pots filled with soil and grown in a greenhouse for 13 days. Compounds 1-16, 18-21, 25, 26, 29-35, 37, 39, 40, 44, 46-49, 54-58, 64, 71-89, or 90 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the foliage of the soybeans, ensuring sufficient coverage of the foliage. After spraying, the soybeans were air-dried, and one day later, they were inoculated by spraying with an aqueous suspension of spores of Soybean spot fungus. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under humid conditions for 3 days, then cultivated in the greenhouse for 16 days, after which the lesion area was examined. The lesion area on soybeans treated with each compound of the present invention was 30% or less of that on untreated soybeans.

[0345] Test Example 21: Control test against tomato ring spot (Alternaria solani) Plastic pots were filled with soil, and tomatoes (variety: Patio) were sown and grown in a greenhouse for 20 days. Compounds 3-6, 9, 11-16, 18-20, 29, 32, 35, 36, 44, 51, 57-59, 68, 71, 75, 76, 80, 86, or 87 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the stems and foliage of the tomatoes, ensuring sufficient coverage of the leaves. After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying with an aqueous suspension of spores of the tomato ring rot fungus. After inoculation, the tomatoes were kept at 18°C ​​under humid conditions for 6 days, and then the lesion area was examined. The lesion area on the tomatoes treated with each compound of the present invention was 30% or less of that on the untreated tomatoes.

[0346] Test Example 22: Control test against kidney bean stem rot (Sclerotinia sclerotiorum) Plastic pots were filled with soil, and kidney beans (variety: Nagauzura Namame) were sown and grown in a greenhouse for 8 days. Compounds 2-16, 18-20, 25, 26, 29, 48, 53, 55, 57, 58, 64, 71, 76, 77, or 89 of the present invention, formulated according to the method described in Formulation Example 6, were mixed with water to a concentration of 200 ppm. The resulting mixture was sprayed on the stems and leaves of the kidney beans so that sufficient adhesion was achieved. After spraying, the kidney beans were air-dried, and PDA medium containing mycelia of Sclerotinia sclerotinia was placed on the kidney bean leaves. After inoculation, all kidney beans were kept under humid conditions overnight, and the lesion area was examined 4 days after inoculation. The lesion area on the kidney beans treated with each compound of the present invention was 30% or less of that on the untreated kidney beans.

[0347] Next, it will be shown that the compounds of the present invention are useful for controlling harmful arthropods.

[0348] Test Method 23 The compound of the present invention is formulated according to the method described in Formulation Example 6, and water containing 0.03% by volume of a wetting agent is added to prepare a diluted solution containing the compound of the present invention at a predetermined concentration. The diluted solution is sprayed at a rate of 20 mL per seedling on cabbage (Brassicae oleracea) seedlings (at the second to third true leaf stage) planted in a container. The stems and leaves of the seedlings are then cut off and placed in a container lined with filter paper. Five second-instar diamondback moth larvae are then released into the solution. After five days, the number of surviving insects is counted, and the mortality rate is calculated using the following formula: Mortality rate %=(1-number of living insects / 5)×100

[0349] Test Example 23 A test was carried out using Compound 28 of the present invention at a predetermined concentration of 500 ppm according to Test Method 23. Compound 28 of the present invention showed a mortality rate of 100%. [Industrial Applicability]

[0350] The compound of the present invention has a controlling effect on pests and can be used for controlling pests.

Claims

1. Formula (I): 【Chemistry 1】 [During the ceremony, L is an oxygen atom or CH 2 represents E is a methyl group substituted with one or more substituents selected from group A, a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, or R 3 R 5 represents NC(O)-, R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different, R 2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; R 3 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more halogen atoms, R 5 represents a methyl group, an ethyl group, a methoxy group, or a hydrogen atom; R 3 and R 5 may be taken together with the nitrogen atom to which R 3 and R 5 are attached to form a 5- to 6-membered non-aromatic heterocyclic group. Group A: a group consisting of OCH 3 , Si(CH 3 ) 3 , a C3-C6 cycloalkyl group, a phenyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 6-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 6-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from the group consisting of a trifluoromethyl group, a halogen atom and a cyano group}, a halogen atom, and a cyano group. or an N-oxide or an agriculturally acceptable salt thereof.

2. The compound according to claim 1, or an N-oxide or an agriculturally acceptable salt thereof, wherein E is a methyl group substituted with one or more substituents selected from group A, or a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A.

3. E is R 3 R 5 2. The compound of claim 1, which is NC(O)-, or an N-oxide or agriculturally acceptable salt thereof.

4. R 1 4. The compound according to claim 1, wherein n is a methyl group or a chlorine atom, n is 0, and L is an oxygen atom, or an N-oxide or an agriculturally acceptable salt thereof.

5. A pest control composition comprising a compound according to any one of claims 1 to 4, or an N-oxide or an agriculturally acceptable salt thereof, and an inert carrier.

6. A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and a compound according to any one of claims 1 to 4, or an N-oxide or an agriculturally acceptable salt thereof: Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): repellent components.

7. A method for controlling pests, which comprises applying to plants or soil an effective amount of the compound according to any one of claims 1 to 4, or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to claim 6.

8. A method for controlling soybean rust fungus having an F129L amino acid substitution in mitochondrial cytochrome b protein, comprising applying an effective amount of the compound according to any one of claims 1 to 4, or an N-oxide or an agriculturally acceptable salt thereof, or the composition according to claim 6 to soybeans or soil in which soybeans are grown.

9. Use of a compound according to any one of claims 1 to 4, or an N-oxide or an agriculturally acceptable salt thereof, or a composition according to claim 6, for controlling pests.

10. A seed or vegetative reproductive organ carrying an effective amount of a compound according to any one of claims 1 to 4, or an N-oxide or an agriculturally acceptable salt thereof, or a composition according to claim 6.

11. Formula (II): 【Chemistry 2】 [During the ceremony, L is an oxygen atom or CH 2 represents R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different, R 2 represents a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom. A compound represented by the formula:

12. R 1 The compound according to claim 11, wherein is a methyl group or a chlorine atom and n is 0.

13. Formula (III): 【Chemistry 3】 [During the ceremony, L is an oxygen atom or CH 2 represents E represents a methyl group substituted with one or more substituents selected from group A, a C2-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, or R3R5NC(O)-; R 1 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different, R 2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; R 3 represents a C1-C3 chain hydrocarbon 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 phenyl group which may be substituted with one or more halogen atoms; R 5 represents a methyl group, an ethyl group, a methoxy group, or a hydrogen atom; R 3 and R 5 may be taken together with the nitrogen atom to which R 3 and R 5 are attached to form a 5- to 6-membered non-aromatic heterocyclic group. Group A: a group consisting of OCH 3 , Si(CH 3 ) 3 , a C3-C6 cycloalkyl group, a phenyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 6-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 6-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from the group consisting of a trifluoromethyl group, a halogen atom and a cyano group}, a halogen atom, and a cyano group. A compound represented by the formula:

14. The compound according to claim 13, wherein E is a methyl group substituted with one or more substituents selected from group A, or a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A.

15. E is R 3 R 5 The compound of claim 13, which is NC(O)-.

16. R 1 The compound according to any one of claims 13 to 15, wherein is a methyl group or a chlorine atom, n is 0, and L is an oxygen atom.

17. Formula (IV): 【Chemistry 4】 [During the ceremony, E represents a methyl group substituted with one or more substituents selected from group A, a C2-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, or R3R5NC(O)-; n represents 0, 1, 2 or 3; When n is 2 or 3, multiple R 2 may be the same or different, R 2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom; R 3 represents a C1-C3 chain hydrocarbon 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 phenyl group which may be substituted with one or more halogen atoms; R 5 represents a methyl group, an ethyl group, a methoxy group, or a hydrogen atom; R 3 and R 5 may be taken together with the nitrogen atom to which R 3 and R 5 are attached to form a 5- to 6-membered non-aromatic heterocyclic group. Group A: a group consisting of OCH 3 , Si(CH 3 ) 3 , a C3-C6 cycloalkyl group, a phenyl group, a 5- to 6-membered aromatic heterocyclic group, a 3- to 6-membered non-aromatic heterocyclic group {the C3-C6 cycloalkyl group, the phenyl group, the 5- to 6-membered aromatic heterocyclic group and the 3- to 6-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from the group consisting of a trifluoromethyl group, a halogen atom and a cyano group}, a halogen atom, and a cyano group. A compound represented by the formula:

18. The compound according to claim 17, wherein n is 0, and E is a methyl group substituted with one or more substituents selected from group A, or a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group A.

19. n is 0 and E is R 3 R 5 The compound of claim 17, which is NC(O)-.

20. Formula (VI): 【Chemistry 5】 [During the ceremony, L is an oxygen atom or CH 2 represents R 1 represents a methyl group or a chlorine atom, n represents 0. A compound represented by the formula:

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