Phenylacetic acid derivatives, their use and manufacturing intermediates thereof

Abstract

This invention provides a compound of formula (I) or its N oxide or salt thereof that has excellent control efficacy against pests. In formula (I), the combination of X and L indicates that X is a nitrogen atom and L is an oxygen atom or a combination of NH, n indicates 1 or 2, E indicates C6-C10 aryl, etc., R 1 and R 2 The same or different from each other indicates C1-C3 chain hydrocarbon groups that can be replaced by more than one halogen atom.

Description

Phenylacetic acid derivatives, their uses and manufacturing intermediates Technical Field

[0001] This patent application asserts priority and interests under the Paris Convention based on Japanese Patent Application No. 2021-029651 (filed on February 26, 2021) and Japanese Patent Application No. 2021-124464 (filed on July 29, 2021), the entire contents of which are incorporated herein by reference.

[0002] This invention relates to phenylacetic acid derivatives, their uses, and intermediates for their manufacture. Background Technology

[0003] Patent document 1 describes a phenylacetic acid derivative.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: European Patent Application Publication No. 422597 Summary of the Invention

[0007] The problem that the invention aims to solve

[0008] The purpose of this invention is to provide compounds that have excellent control efficacy against harmful organisms.

[0009] Methods for solving problems

[0010] The inventors of this application conducted research in order to find compounds with excellent control efficacy against pests, and found that the compound represented by the following formula (I) has excellent control efficacy against pests.

[0011] That is, the present invention is as follows.

[0012] [1] The compound represented by formula (I) (hereinafter referred to as compound N of the present invention) or its N oxide or salt thereof (hereinafter, the compound represented by formula (I) or its N oxide or salt thereof is referred to as compound of the present invention).

[0013] [Chemical Formula 1]

[0014]

[0015] In the formula,

[0016] The combination of X and L represents:

[0017] X is a nitrogen atom and L is an oxygen atom or a combination of NH, or,

[0018] X is a combination of CH and L is an oxygen atom;

[0019] n represents 1 or 2,

[0020] E represents a C6-C10 aryl group that can be substituted by one or more substituents selected from group A; a 5-10 membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B; a C3-C7 cycloalkenyl group that can be substituted by one or more substituents selected from group C; and R represents... 3 -ON=C(R 4 )-、R 5 -C≡C-、or R 6 O-,

[0021] R 1 and R 2 "Same" or "different" indicates a C1-C3 chain hydrocarbon group, methoxy group, cyclopropyl group, or halogen atom that can be substituted by one or more halogen atoms.

[0022] R 3 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group G, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, a C6-C10 aryl group, a 5-10 member aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 member aromatic heterocyclic group can be substituted by one or more substituents selected from group F}, or R. 7 CH2-,

[0023] R 4 This refers to a C1-C3 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms.

[0024] R 5 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group D, or a C3-C6 cycloalkyl, phenyl, or 5-6 membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group E {the phenyl and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group F}.

[0025] R 6 This indicates a methyl group substituted with one or more substituents selected from group G, a C2-C6 chain hydrocarbon group substituted with one or more substituents selected from group D, or a C3-C4 cycloalkyl group substituted with one or more substituents selected from group E.

[0026] R 7 It represents a phenyl group or a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group F}.

[0027] Group A: Composed of C1-C6 chain hydrocarbon groups, C1-C3 alkyl thio groups {where the C1-C6 chain hydrocarbon group and the C1-C3 alkyl thio group can be substituted by one or more substituents selected from Group G}, C3-C6 cycloalkyl groups that can be substituted by one or more substituents selected from Group E, OR 10 C(O)R 8 C(O)OR 8 C(O)NR 8 R 9 NR 8 R 9 C(R) 11 ) = N - OR 12 The group consisting of phenyl, 5-6 membered aromatic heterocyclic group (the phenyl and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group F), halogen atom, cyano, and nitro.

[0028] R 8 and R 9 "Same" or "different" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group G, a C3-C6 cycloalkyl group, phenyl group, 5-6 membered aromatic heterocyclic group (the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group F), or a hydrogen atom.

[0029] R 10 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group G, or a C3-C6 cycloalkyl, phenyl, or 5-6 membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group E {the phenyl and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group F}.

[0030] R 11 This refers to a C1-C3 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms.

[0031] R 12 It represents a C1-C3 chain hydrocarbon group that can be substituted by one or more substituents selected from group D, a C3-C6 cycloalkyl group, a C6-C10 aryl group, and a 5-10 member aromatic heterocyclic group that can be substituted by one or more substituents selected from group E {the C6-C10 aryl group and the 5-10 member aromatic heterocyclic group can be substituted by one or more substituents selected from group F}.

[0032] Group B: Composed of C3-C6 cycloalkyl, C1-C6 chain hydrocarbon, C1-C3 alkylthio group (the C1-C6 chain hydrocarbon and the C1-C3 alkylthio group may be substituted by one or more substituents selected from Group G), phenyl, 5-6 membered aromatic heterocyclic group (the phenyl and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from Group F), OR 13 C(O)R 8 C(O)OR 8 C(O)NR 8 R 9 NR 8 R 9 C(R) 11 ) = N - OR 12 It is a group composed of halogen atoms, cyano groups, and nitro groups.

[0033] R 13 It indicates a C3-C6 cycloalkyl group, a C1-C6 chain hydrocarbon group (which may be substituted by one or more substituents selected from the group consisting of C3-C6 cycloalkyl and C1-C3 alkoxy groups), a phenyl group, a 5-6 membered aromatic heterocyclic group (which may be substituted by one or more substituents selected from the group F), or a trifluoromethyl group that can be substituted by one or more substituents selected from the group E.

[0034] Group C: Composed of a C1-C4 chain hydrocarbon group, a C1-C3 alkoxy group (the C1-C4 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted by one or more halogen atoms), a halogen atom, a cyano group, an oxo group, and (=NOR) 13 A group consisting of ).

[0035] Group D: The group consisting of C1-C6 alkoxy groups, C1-C6 alkylthio groups (the C1-C6 alkoxy and C1-C6 alkylthio groups may be substituted by one or more substituents selected from Group G), C3-C6 cycloalkyl groups, 3-8 membered non-aromatic heterocyclic groups (the C3-C6 cycloalkyl and 3-8 membered non-aromatic heterocyclic groups may be substituted by one or more substituents selected from Group E), C6-C10 aryl groups, 5-10 membered aromatic heterocyclic groups (the C6-C10 aryl and 5-10 membered aromatic heterocyclic groups may be substituted by one or more substituents selected from Group F), halogen atoms, cyano groups, nitro groups, and hydroxyl groups.

[0036] Group E: Composed of a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group, a C3-C6 cycloalkyl group {the C1-C3 chain hydrocarbon group, the C1-C3 alkoxy group, and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}, an oxo group, a halogen atom, a cyano group, and (=NOR) 4 A group consisting of ).

[0037] Group F: The group consisting of C1-C3 chain hydrocarbon group, C3-C6 cycloalkyl group, C1-C3 alkoxy group, C1-C3 alkylthio group {the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group, and the C1-C3 alkylthio group may be substituted by one or more substituents selected from Group G}, halogen atom, cyano group, nitro group, and hydroxyl group.

[0038] Group G: A group composed of C3-C6 cycloalkyl groups, C1-C3 alkoxy groups, and halogen atoms.

[0039] [2] The compound as described in [1] or its N oxide or salt thereof, wherein n is 1,

[0040] R 1 and R 2 The same or different from each other, being C1-C3 alkyl, methoxy, or halogen atoms that can be substituted by one or more halogen atoms.

[0041] R 2 Bonded to 4 or 5 bits

[0042] E represents a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group H}, and R represents a phenyl group. 3 -ON=C(R 4 )-、R 5 -C≡C-、R 6 O- or C5-C6 cycloalkenyl groups,

[0043] R 3 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group G, a C3-C6 cycloalkyl group that can be substituted by one or more halogen atoms, or R 7 CH2-,

[0044] R 4 It consists of C1-C3 chain hydrocarbon groups or hydrogen atoms.

[0045] R 5 It is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms}.

[0046] R 6 It is a C2-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group that can be substituted by one or more substituents selected from Group I.

[0047] R 7 It is a phenyl or a 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group J}.

[0048] Group H: The group consisting of C1-C3 chain hydrocarbon groups, C1-C3 alkoxy groups, trifluoromethoxy groups, C3-C4 cycloalkyl groups, halogen atoms, cyano groups, and nitro groups that can be substituted by one or more halogen atoms.

[0049] Group I: The group consisting of C3-C6 cycloalkyl, C1-C3 alkoxy, phenyl (the C1-C3 alkoxy and the phenyl may be substituted by one or more halogen atoms), and halogen atoms.

[0050] Group J: The group consisting of C1-C3 chain hydrocarbon groups, C1-C3 alkoxy groups (the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted by one or more halogen atoms), C3-C6 cycloalkyl groups, halogen atoms, cyano groups, and nitro groups.

[0051] [3] The compound as described in [2] or its N oxide or salt thereof, wherein E is phenyl, pyridyl, thiophenyl, thiazolyl, pyrazolyl {the phenyl, pyridyl, thiophenyl, thiazolyl, and pyrazolyl may be substituted by one or more substituents selected from group H}, R 5 -C≡C-、R 6 O- or C5-C6 cycloalkenyl groups.

[0052] [4] A pesticide composition containing any one of [1] to [3], or its N oxide or salt, or an inactive support.

[0053] [5] A composition comprising one or more ingredients selected from the groups (a), (b), (c) and (d), and a compound or its N oxide or salt thereof as described in any one of [1] to [3].

[0054] Group (a): A group consisting of insecticidal, acaricidal, and nematicidal active ingredients;

[0055] Group (b): Bactericidal active ingredient;

[0056] Group (c): Plant growth regulators;

[0057] Group (d): Repellent component.

[0058] [6] A method for controlling pests, which is carried out by treating plants or soil with an effective amount of any one of the compounds in [1] to [3] or their N oxides or salts or the effective amount of the composition described in [5].

[0059] [7] A method for controlling soybean rust fungus with an amino acid substitution of F129L in mitochondrial cytochrome b protein, which is carried out by applying an effective amount of any one of the compounds in [1] to [3] or their N oxides or salts thereof or an effective amount of the composition described in [5] to soybeans or the soil for soybean growth.

[0060] The use of any one of the compounds in [8], [1] to [3] or their N oxides or salts, or the composition described in [5] for the control of pests.

[0061] [9] A seed or vegetative reproductive organ containing an effective amount of any one of [1] to [3], or its N oxide or salt thereof, or an effective amount of the composition described in [5].

[0062]

[10] The compound represented by formula (II) (hereinafter referred to as intermediate A).

[0063] [Chemical Formula 2]

[0064]

[0065] In the formula,

[0066] The combination of X and L represents:

[0067] X is a nitrogen atom and L is an oxygen atom or a combination of NH, or,

[0068] X is a combination of CH and L is an oxygen atom;

[0069] E a R represents 12a C(O)-, R 12a C(=N-OH)-, hydroxyl group, B(OH)2, 4,

[0070] 4,5,5-Tetramethyl-1,3,2-dioxacyclopentaborane-2-yl, or halogen atom,

[0071] R 1a and R 2a The same or different from each other indicates methyl or halogen atoms.

[0072] R 12a This indicates a C1-C3 alkyl group or a hydrogen atom.

[0073] Invention Effects

[0074] This invention enables the prevention and control of harmful organisms. Detailed Implementation

[0075] The substituents in this invention will be explained.

[0076] Halogen atoms refer to fluorine, chlorine, bromine, or iodine atoms.

[0077] When a substituent is replaced by two or more halogen atoms, these halogen atoms may be the same or different.

[0078] When a substituent is replaced by two or more groups or atoms selected from a specific group (e.g., a group consisting of C1-C3 alkyl and halogen atoms), these groups or atoms may be the same or different.

[0079] Regarding the statement in this specification that "can be substituted by one or more substituents selected from group X" (X refers to any one of A, B, C, D, E, F, G, H, I, J, and K), when there are two or more substituents selected from group X, these substituents may be the same or different.

[0080] In this specification, expressions such as "CX-CY" refer to carbon atoms ranging from X to Y. For example, expressions such as "C1-C6" refer to carbon atoms ranging from 1 to 6.

[0081] The term "chain hydrocarbon group" refers to alkyl, alkenyl, or alkynyl groups.

[0082] Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, and decyl.

[0083] 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.

[0084] Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, 5-hexynyl, and 9-decynyl.

[0085] Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentoxy, and hexyloxy.

[0086] Examples of alkyl thio groups include methyl thio, ethyl thio, propyl thio, isopropyl thio, butyl thio, tert-butyl thio, pentyl thio, and hexyl thio.

[0087] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0088] Examples of cycloalkenyl groups include cyclopentenyl and cyclohexenyl.

[0089] Examples of aryl groups include phenyl, indene, indanyl, naphthyl, and tetrahydronaphthyl.

[0090] Examples of aromatic heterocyclic groups include pyrroleyl, furanyl, thiophenyl, pyrazolyl, imidazoleyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, pyridinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, inzolyl, benzimidazolyl, imidazolepyridyl, benzobenzylthio, benzofuranyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxolinyl.

[0091] The terminology used in this specification is explained.

[0092] The soybean rust fungus with the F129L amino acid substitution in the mitochondrial cytochrome b protein is the following soybean rust fungus (scientific name: Phakopsora pachyrhizi): It has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein. As a result of this mutation, the F129L amino acid substitution has occurred, thereby showing resistance to QoI fungicide.

[0093] The compound and intermediate A of this invention sometimes contain more than one stereoisomer. Examples of stereoisomers include enantiomers, diastereomers, transisomers, and geometric isomers. This invention includes each stereoisomer and mixtures of stereoisomers in any ratio.

[0094] As a geometric isomer, the following structures can be cited as examples.

[0095] [Chemical Formula 3]

[0096]

[0097] The compound N or its N oxide of the present invention sometimes forms acid addition salts such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid by mixing with acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid.

[0098] Examples of compounds N in this invention include the following compounds.

[0099] [Method 1] In compound N of the present invention, E is R 3 -ON=C(R 4 Compounds of )-.

[0100] [Method 2] In Method 1, R 3It is a C1-C6 chain hydrocarbon group {this C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of C3-C4 cycloalkyl and halogen atoms}, or R 7 CH2-, R 4 R is a methyl or hydrogen atom. 7 Compounds that are phenyl or 5-6 membered aromatic heterocyclic groups {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group K}.

[0101] Group K: A group consisting of C1-C3 chain hydrocarbon groups that can be replaced by one or more halogen atoms and halogen atoms.

[0102] [Method 3] In compound N of the present invention, E is R 5 Compounds of -C≡C-.

[0103] [Method 4] In Method 3, R 5 Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups.

[0104] [Method 5] In compound N of the present invention, E is R 6 Compounds of O-.

[0105] [Method 6] In Method 5, R 6 It is a compound that can be substituted by one or more substituents selected from Group I, and is a C2-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.

[0106] [Method 7] In compound N of the present invention, E is a phenyl compound that can be substituted by one or more substituents selected from group A.

[0107] [Method 8] In compound N of the present invention, E is a phenyl compound that can be substituted by one or more substituents selected from group H.

[0108] [Method 9] In compound N of the present invention, E is a 5-6 membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B.

[0109] [Method 10] In compound N of the present invention, E is a 5-6 membered aromatic heterocyclic compound that can be substituted by one or more substituents selected from group H.

[0110] [Method 11] In the compound N of the present invention, E is a compound of pyridyl, thiophene, thiazolyl, or pyrazolyl {the pyridyl, thiophene, thiazolyl, and pyrazolyl may be substituted by one or more substituents selected from group H}.

[0111] [Method 12] In the compound N of the present invention, E is a compound of pyridyl, thiophene, thiazolyl, or pyrazolyl {the pyridyl, thiophene, thiazolyl, and pyrazolyl may be substituted by one or more substituents selected from group K}.

[0112] [Method 13] In compound N of the present invention, E is a C5-C6 cycloalkenyl compound.

[0113] [Method 14] In compound N of the present invention, E is phenyl {the phenyl group may be substituted by one or more substituents selected from group H}, pyridyl, thiophene, thiazolyl, pyrazolyl {the pyridyl, thiophene, thiazolyl, and pyrazolyl may be substituted by one or more substituents selected from group K}, C5-C6 cycloalkenyl, R 3 -ON=C(R 4 )-、R 5 -C≡C-、or R 6 O-, R 3 It is a C1-C6 chain hydrocarbon group {this C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of C3-C4 cycloalkyl and halogen atoms}, or R 7 CH2-, R 4 R is a methyl or hydrogen atom. 5 It is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, R 6 R is a C2-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group that can be substituted by one or more substituents selected from Group I. 7 Compounds that are phenyl or 5-6 membered aromatic heterocyclic groups {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group K}.

[0114] [Method 15] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group A}, a 5-6 membered aromatic heterocyclic group {which may be substituted by one or more substituents selected from group H}, a C3-C7 cycloalkenyl group substituted by one or more substituents selected from group C, and R 5 -C≡C-、or R 6 O-, R 5 Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups {where the C1-C6 chain hydrocarbon group or the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}.

[0115] [Method 16] In compound N of the present invention, E is phenyl {the phenyl group may be substituted by one or more substituents selected from group H}, pyridyl, thiophene, thiazolyl, pyrazolyl {the pyridyl, thiophene, thiazolyl, and pyrazolyl may be substituted by one or more substituents selected from group K}, C5-C6 cycloalkenyl, R 5-C≡C-、or R 6 O-, R 5 It is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, R 6 It is a compound that can be substituted by one or more substituents selected from Group I, and is a C2-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.

[0116] [Method 17] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group A}, a 5-6 membered aromatic heterocyclic group {which may be substituted by one or more substituents selected from group H}, R 5 -C≡C-、or R 6 O-, R 5 Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups {where the C1-C6 chain hydrocarbon group or the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}.

[0117] [Method 18] In compound N of the present invention, E is phenyl {the phenyl group may be substituted by one or more substituents selected from group H}, pyridyl, thiophene, thiazolyl, pyrazolyl {the pyridyl, thiophene, thiazolyl, and pyrazolyl may be substituted by one or more substituents selected from group K}, R 5 -C≡C-、or R 6 O-, R 5 It is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, R 6 It is a compound that can be substituted by one or more substituents selected from Group I, and is a C2-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.

[0118] [Method 19] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group A}, a 5-6 membered aromatic heterocyclic group {which may be substituted by one or more substituents selected from group H}, or R 5 -C≡C-,R 5 Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups {where the C1-C6 chain hydrocarbon group or the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}.

[0119] [Method 20] In compound N of the present invention, E is phenyl {the phenyl group may be substituted by one or more substituents selected from group H}, pyridyl, thiophene, thiazolyl, pyrazolyl {the pyridyl, thiophene, thiazolyl, and pyrazolyl may be substituted by one or more substituents selected from group K}, or R 5 -C≡C-,R 5 Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups.

[0120] [Method 21] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group A}, a 5-6 membered aromatic heterocyclic group {which may be substituted by one or more substituents selected from group H}, or R 6 Compounds of O-.

[0121] [Method 22] In compound N of the present invention, E is phenyl {the phenyl group may be substituted by one or more substituents selected from group H}, pyridyl, thiophene, thiazolyl, pyrazolyl {the pyridyl, thiophene, thiazolyl, and pyrazolyl may be substituted by one or more substituents selected from group K}, or R 6 O-, R 6 It is a compound that can be substituted by one or more substituents selected from Group I, and is a C2-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.

[0122] [Method 23] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group A}, R 5 -C≡C-、or R 6 O-, R 5 Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups {where the C1-C6 chain hydrocarbon group or the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}.

[0123] [Method 24] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group H}, R 5 -C≡C-、or R 6 O-, R 5 It is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, R 6 It is a compound that can be substituted by one or more substituents selected from Group I, and is a C2-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.

[0124] [Method 25] In compound N of the present invention, E is a phenyl group {the phenyl group may be substituted by one or more substituents selected from group A} or a 5-6 membered aromatic heterocyclic group {the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group H}.

[0125] [Method 26] In compound N of the present invention, E is a compound of phenyl {the phenyl group may be substituted by one or more substituents selected from group H}, pyridyl, thiophene, thiazolyl, or pyrazolyl {the pyridyl, thiophene, thiazolyl, and pyrazolyl group may be substituted by one or more substituents selected from group K}.

[0126] [Method 27] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group A}, or R 5-C≡C-,R 5 Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups {where the C1-C6 chain hydrocarbon group or the C3-C6 cycloalkyl group may be substituted by one or more halogen atoms}.

[0127] [Method 28] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group H}, or R 5 -C≡C-,R 5 Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups.

[0128] [Method 29] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group A}, or R 6 Compounds of O-.

[0129] [Method 30] In compound N of the present invention, E is a phenyl group {which may be substituted by one or more substituents selected from group H}, or R 6 O-, R 6 It is a compound that can be substituted by one or more substituents selected from Group I, and is a C2-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.

[0130] [Method 31] A compound of the present invention in which X is CH and L is an oxygen atom.

[0131] [Method 32] A compound in Method 1 where X is CH and L is an oxygen atom.

[0132] [Method 33] A compound in Method 2 where X is CH and L is an oxygen atom.

[0133] [Method 34] A compound in Method 3 in which X is CH and L is an oxygen atom.

[0134] [Method 35] A compound in Method 4 where X is CH and L is an oxygen atom.

[0135] [Method 36] A compound in Method 5 where X is CH and L is an oxygen atom.

[0136] [Method 37] A compound in Method 6 where X is CH and L is an oxygen atom.

[0137] [Method 38] A compound in Method 7 where X is CH and L is an oxygen atom.

[0138] [Method 39] A compound in Method 8 where X is CH and L is an oxygen atom.

[0139] [Method 40] A compound in Method 9 where X is CH and L is an oxygen atom.

[0140] [Method 41] A compound in Method 10 in which X is CH and L is an oxygen atom.

[0141] [Method 42] A compound in Method 11 where X is CH and L is an oxygen atom.

[0142] [Method 43] A compound in Method 12 where X is CH and L is an oxygen atom.

[0143] [Method 44] A compound in Method 13 in which X is CH and L is an oxygen atom.

[0144] [Method 45] A compound in Method 14 where X is CH and L is an oxygen atom.

[0145] [Method 46] A compound in Method 15 where X is CH and L is an oxygen atom.

[0146] [Method 47] A compound in Method 16 where X is CH and L is an oxygen atom.

[0147] [Method 48] A compound in Method 17 where X is CH and L is an oxygen atom.

[0148] [Method 49] A compound in Method 18 where X is CH and L is an oxygen atom.

[0149] [Method 50] A compound in Method 19 where X is CH and L is an oxygen atom.

[0150] [Method 51] A compound in Method 20 in which X is CH and L is an oxygen atom.

[0151] [Method 52] A compound in Method 21 where X is CH and L is an oxygen atom.

[0152] [Method 53] A compound in Method 22 where X is CH and L is an oxygen atom.

[0153] [Method 54] A compound in Method 23 in which X is CH and L is an oxygen atom.

[0154] [Method 55] A compound in Method 24 where X is CH and L is an oxygen atom.

[0155] [Method 56] A compound in Method 25 where X is CH and L is an oxygen atom.

[0156] [Method 57] A compound in Method 26 where X is CH and L is an oxygen atom.

[0157] [Method 58] A compound in Method 27 where X is CH and L is an oxygen atom.

[0158] [Method 59] A compound in Method 28 where X is CH and L is an oxygen atom.

[0159] [Method 60] A compound in Method 29 where X is CH and L is an oxygen atom.

[0160] [Method 61] A compound in Method 30 where X is CH and L is an oxygen atom.

[0161] [Method 62] In any of methods 1 to 61 or compound N of the present invention, R 1 It is a compound of C1-C3 alkyl, methoxy, or halogen atoms that can be substituted by one or more halogen atoms.

[0162] [Method 63] In any of methods 1 to 61 or compound N of the present invention, R 1 Compounds containing methyl, methoxy, or halogen atoms.

[0163] [Method 64] In any of methods 1 to 61 or compound N of the present invention, R 1 Compounds containing methyl groups.

[0164] [Method 65] In any of methods 1 to 61 or compound N of the present invention, R 2 It is a compound of C1-C3 alkyl, methoxy, or halogen atoms that can be substituted by one or more halogen atoms.

[0165] [Method 66] In any of methods 1 to 61 or compound N of the present invention, R 2 Compounds containing methyl, methoxy, or halogen atoms.

[0166] [Method 67] In any of methods 1 to 61 or compound N of the present invention, R 2 Compounds containing methyl groups.

[0167] [Method 68] In any of methods 1 to 61 or compound N of the present invention, R 1 and R 2 Compounds that are the same as or different from each other, and are C1-C3 alkyl, methoxy, or halogen atoms that can be substituted with one or more halogen atoms.

[0168] [Method 69] In any of Methods 1 to 61 or Compound N of the present invention, R 1 R is a methyl, methoxy, or halogen atom. 2 It is a compound of C1-C3 alkyl, methoxy, or halogen atoms that can be substituted by one or more halogen atoms.

[0169] [Method 70] In any of Methods 1 to 61 or Compound N of the present invention, R 1 For methyl, R 2 It is a compound of C1-C3 alkyl, methoxy, or halogen atoms that can be substituted by one or more halogen atoms.

[0170] [Method 71] In any of Methods 1 to 61 or Compound N of the present invention, R 1 and R 2 Compounds that are the same or different from each other, and that have methyl, methoxy, or halogen atoms.

[0171] [Method 72] In any of Methods 1 to 61 or Compound N of the present invention, R 1 For methyl, R 2 Compounds containing methyl, methoxy, or halogen atoms.

[0172] [Method 73] In any of Methods 1 to 61 or Compound N of the present invention, R 1 and R 2 Compounds containing methyl groups.

[0173] [Method 74] A compound in any of Methods 1 to 61 or Compound N of the present invention, wherein n is 1.

[0174] [Method 75] The compound in Method 68 where n is 1.

[0175] [Method 76] The compound in Method 69 where n is 1.

[0176] [Method 77] The compound in Method 70 where n is 1.

[0177] [Method 78] The compound in Method 71 where n is 1.

[0178] [Method 79] The compound in Method 72 where n is 1.

[0179] [Method 80] The compound in Method 73 where n is 1.

[0180] [Method 81] In any of Methods 1 to 61 or Compound N of the present invention, n is 1 and R 2 Compounds bonded at the 4 or 5 position.

[0181] [Method 82] In Method 68, n is 1 and R 2 Compounds bonded at the 4 or 5 position.

[0182] [Method 83] In Method 69, n is 1 and R 2 Compounds bonded at the 4 or 5 position.

[0183] [Method 84] In Method 70, n is 1 and R 2 Compounds bonded at the 4 or 5 position.

[0184] [Method 85] In Method 71, n is 1 and R 2 Compounds bonded at the 4 or 5 position.

[0185] [Method 86] In Method 72, n is 1 and R 2 Compounds bonded at the 4 or 5 position.

[0186] [Method 87] In Method 73, n is 1 and R 2 Compounds bonded at the 4 or 5 position.

[0187] [Method 88] In any of Methods 1 to 61 or Compound N of the present invention, n is 1 and R 2 Compounds bonded at position 4.

[0188] [Method 89] In Method 68, n is 1 and R 2 Compounds bonded at position 4.

[0189] [Method 90] In Method 69, n is 1 and R 2 Compounds bonded at position 4.

[0190] [Method 91] In Method 70, n is 1 and R 2 Compounds bonded at position 4.

[0191] [Method 92] In Method 71, n is 1 and R 2 Compounds bonded at position 4.

[0192] [Method 93] In Method 72, n is 1 and R 2 Compounds bonded at position 4.

[0193] [Method 94] In Method 73, n is 1 and R 2 Compounds bonded at position 4.

[0194] In the compound N of this invention, n is 1 and R 2 Compounds bonded at position 4 are those represented by formula (I-4).

[0195] [Chemical Formula 4]

[0196]

[0197] [In the formula, the symbols represent the meanings defined in [1].]

[0198] Compounds of schemes 88 to 94 can also be represented by formula (I-4).

[0199] Next, the method for manufacturing the compound of the present invention will be described.

[0200] Manufacturing Method A

[0201] The compound represented by formula (A1) (hereinafter referred to as compound (A1)) can be prepared by reacting the compound represented by formula (B1) (hereinafter referred to as compound (B1)) with the compound represented by formula (M1) (hereinafter referred to as compound (M1)) in the presence of a palladium catalyst and a base.

[0202] [Chemical Formula 5]

[0203]

[0204] [In the formula, E] 1 M represents a C6-C10 aryl group or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group A}. 1 [This represents B(OH)2 or 4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl, X1 represents leaving groups such as chlorine, bromine, iodine, and trifuranyloxy groups, and other symbols have the same meaning as described above.]

[0205] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons such as hexane, toluene, and xylene; ethers such as methyl tert-butyl ether (MTBE), tetrahydrofuran (THF), and dimethoxyethane (ethers); halogenated hydrocarbons such as chloroform and chlorobenzene (halogenated hydrocarbons); amides such as dimethylformamide (DMF) and N-methylpyrrolidone (NMP); esters such as methyl acetate and ethyl acetate (esters); nitriles such as acetonitrile and propionitrile (nitriles); water and mixtures of two or more of these.

[0206] Examples of palladium catalysts used in the reaction include tris(dibenzylacetone)palladium(0) (hereinafter referred to as Pd2(dba)3), tetra(triphenylphosphine)palladium(0) (hereinafter referred to as Pd(PPh3)4), and {1,1'-bis(diphenylphosphine)ferrocene}palladium(II) dichloride (hereinafter referred to as PdCl2(dppf)).

[0207] Examples of bases used in reactions 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 fluoride and tripotassium phosphate.

[0208] In the reaction, ligands can be used as needed. Examples of ligands used in the reaction include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, and 1,2-bis(diphenylphosphino)ethane. When using ligands in the reaction, the ligand is typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (B1).

[0209] In the reaction, compound (M1) is typically used in a ratio of 1 to 10 moles relative to 1 mole of compound (B1), palladium catalyst is typically used in a ratio of 0.01 to 1 mole, and base is typically used in a ratio of 1 to 10 moles.

[0210] The reaction temperature is typically in the range of 0–150°C. The reaction time is typically in the range of 0.1–120 hours.

[0211] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (A1).

[0212] The compound (M1) is known or can be manufactured using known methods.

[0213] Manufacturing method B

[0214] Compound (A1) can be prepared by reacting the compound represented by formula (B2) (hereinafter referred to as compound (B2)) with the compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of a palladium catalyst and a base.

[0215] [Chemical Formula 6]

[0216]

[0217] [In the formula, the symbols represent the same meaning as described above.]

[0218] The reaction can be carried out in accordance with manufacturing method A, using compound (M2) instead of compound (B1) and compound (B2) instead of compound (M1).

[0219] The compound (M2) is known or can be manufactured using known methods.

[0220] Manufacturing method C

[0221] The compound represented by formula (A2) (hereinafter referred to as compound (A2)) can be prepared by reacting compound (B1) with the compound represented by formula (M3) (hereinafter referred to as compound (M3)) in the presence of a metal catalyst and a base.

[0222] [Chemical Formula 7]

[0223]

[0224] [In the formula, the symbols represent the same meaning as described above.]

[0225] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more of them.

[0226] Examples of metal catalysts used in the reaction include bis(triphenylphosphine)palladium(II) chloride and copper(I) iodide.

[0227] Examples of bases used in reactions include organic bases.

[0228] In the reaction, relative to 1 mole of compound (B1), compound (M3) is usually used in a ratio of 1 to 10 moles, metal catalyst is usually used in a ratio of 0.01 to 1 mole, and base is usually used in a ratio of 1 to 10 moles.

[0229] The reaction temperature is typically in the range of 0–150°C. The reaction time is typically in the range of 0.1–120 hours.

[0230] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate compound (A2).

[0231] The compound (M3) is known or can be manufactured using known methods.

[0232] Manufacturing method D

[0233] The compound represented by formula (A3) (hereinafter referred to as compound (A3)) can be produced by reacting the compound represented by formula (B3) (hereinafter referred to as compound (B3)) with the compound represented by formula (M4) (hereinafter referred to as compound (M4)) or a salt thereof.

[0234] [Chemical Formula 8]

[0235]

[0236] [In the formula, the symbols represent the same meaning as described above.]

[0237] Examples of salts of compound (M4) include hydrochloride and sulfate.

[0238] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; alcohols such as methanol and ethanol (hereinafter referred to as alcohols); and mixtures of two or more of them.

[0239] In the reaction, a base may be added as needed. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkali metal bicarbonates; sodium hydride; and tripotassium phosphate. When a base is used in the reaction, it is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B3).

[0240] In the reaction, compound (M4) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B3).

[0241] The reaction temperature is typically in the range of 0–150°C. The reaction time is typically in the range of 0.1–120 hours.

[0242] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (A3).

[0243] Alternatively, compound (A3) can also be manufactured according to the methods described in International Publication No. 98 / 043949, etc.

[0244] The compound (M4) is known or can be manufactured using known methods.

[0245] Manufacturing method E

[0246] Compound (A3) can be prepared by reacting the compound represented by formula (B4) (hereinafter referred to as compound (B4)) with the compound represented by formula (M5) (hereinafter referred to as compound (M5)) in the presence of a base.

[0247] [Chemical Formula 9]

[0248]

[0249] [In the formula, the symbols represent the same meaning as described above.]

[0250] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more of them.

[0251] Examples of bases include organic bases, alkali metal carbonates, alkali metal bicarbonates, sodium hydride, and tripotassium phosphate.

[0252] In the reaction, compound (M5) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B4), and the base is usually used in a ratio of 1 to 10 moles.

[0253] The reaction temperature is typically in the range of -20 to 150°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0254] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (A3).

[0255] The compound (M5) is known or can be manufactured using known methods.

[0256] Manufacturing method F

[0257] The compound represented by formula (A4) (hereinafter referred to as compound (A4)) can be prepared by reacting compound (B1) with the compound represented by formula (M6) (hereinafter referred to as compound (M6)) in the presence of a metal catalyst and a base.

[0258] [Chemical Formula 10]

[0259]

[0260] [In the formula, Z] 1 Represents nitrogen atom or CR 51 Z 2 Represents nitrogen atom or CR 52 Z 3 Represents nitrogen atom or CR 53 Z 4 Represents nitrogen atom or CR 54 (excluding Z) 1 Z 2 Z 3 and Z 4 (The case where all atoms are nitrogen) R 51 R 52 R 53 and R 54"Identical" or "different from each other" indicates C3-C6 cycloalkyl, C1-C6 chain hydrocarbon, C1-C3 alkylthio group (the C1-C6 chain hydrocarbon and the C1-C3 alkylthio group may be substituted by one or more substituents selected from group E), phenyl, 5-6 membered aromatic heterocyclic group (the phenyl and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group F), OR 13 C(O)R 8 C(O)OR 8 C(O)NR 8 R 9 NR 8 R 9 C(R) 11 ) = N - OR 12 [Halogen atom, cyano group, nitro group, or hydrogen atom; other symbols have the same meaning as described above.]

[0261] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, hydrocarbons, amides, water, and mixtures of two or more of them.

[0262] Examples of metal catalysts used in the reaction include copper catalysts such as copper iodide (I), copper bromide (I), copper chloride (I), copper oxide (I), copper trifluoromethanesulfonate (I) benzene complex, copper tetra(acetonitrile) hexafluorophosphate (I), and copper 2-thiophenecarboxylate (I); and nickel catalysts such as bis(cyclooctadiene) nickel (O) and nickel chloride (II).

[0263] Examples of bases include organic bases, alkali metal carbonates, alkali metal bicarbonates, sodium fluoride, and tripotassium phosphate.

[0264] In the reaction, ligands and / or alkali metal halides may be used as needed.

[0265] Examples of ligands include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, and N,N'-dimethylethylenediamine. When using ligands in a reaction, the ligand is typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (B1).

[0266] Examples of alkali metal halides include potassium fluoride, sodium fluoride, lithium chloride, and sodium chloride. When using alkali metal halides in reactions, the ratio of the alkali metal halide to alkali metal halide is usually 0.1 to 5 moles relative to 1 mole of compound (B1).

[0267] In the reaction, compound (M6) is typically used in a ratio of 1 to 10 moles relative to 1 mole of compound (B1), metal catalyst is typically used in a ratio of 0.01 to 2 moles, and base is typically used in a ratio of 1 to 10 moles.

[0268] The reaction temperature is typically in the range of -20℃ to 200℃. The reaction time is typically in the range of 0.1 to 48 hours.

[0269] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (A4).

[0270] The compound (M6) is known or can be manufactured using known methods.

[0271] Manufacturing method G

[0272] The compound represented by formula (A5) (hereinafter referred to as compound (A5)) can be prepared by reacting the compound represented by formula (B5) (hereinafter referred to as compound (B5)) with the compound represented by formula (M7) (hereinafter referred to as compound (M7)) in the presence of phosphine and azo diester.

[0273] [Chemical Formula 11]

[0274]

[0275] [In the formula, the symbols represent the same meaning as described above.]

[0276] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles and mixtures of two or more of them.

[0277] Examples of phosphine derivatives include triphenylphosphine and trimethylphosphine.

[0278] Examples of azodiesters include diethyl azodicarbonate, diisopropyl azodicarbonate, and bis(2-methoxyethyl) azodicarbonate.

[0279] In the reaction, relative to 1 mole of compound (B5), compound (M7) is usually used in a ratio of 1 to 10 moles, phosphines are usually used in a ratio of 1 to 10 moles, and azodicarbonates are usually used in a ratio of 1 to 10 moles.

[0280] The reaction temperature is typically in the range of 0–150°C. The reaction time is typically in the range of 0.1–48 hours.

[0281] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (A5).

[0282] The compound (M7) is known or can be manufactured using known methods.

[0283] Manufacturing method H

[0284] Compound (A5) can also be prepared by reacting compound (B5) with the compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a base.

[0285] [Chemical Formula 12]

[0286]

[0287] [In the formula, the symbols represent the same meaning as described above.]

[0288] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more of them.

[0289] Examples of bases include organic bases, alkali metal carbonates, alkali metal bicarbonates, sodium hydride, and tripotassium phosphate.

[0290] In the reaction, compound (M8) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B5), and the base is usually used in a ratio of 1 to 10 moles.

[0291] The reaction temperature is typically in the range of -20 to 150°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0292] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (A5).

[0293] The compound (M8) is known or can be manufactured using known methods.

[0294] Manufacturing Method I

[0295] The compound represented by formula (A6) (hereinafter referred to as compound (A6)) can be manufactured by the following steps: reacting the compound represented by formula (B6) (hereinafter referred to as compound (B6)) with the compound represented by formula (M9) (hereinafter referred to as compound (M9)) in the presence of a base to obtain the compound represented by formula (B7) (hereinafter referred to as step (I-1)); and reacting the compound (B7) with the compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base (hereinafter referred to as step (I-2)).

[0296] [Chemical Formula 13]

[0297]

[0298] In the formula, R 55 Indicates C1-C4 alkyl, X 2 [This indicates an iodine atom, methoxysulfonyloxy, methanesulfonyloxy, or toluenesulfonyloxy; other symbols have the same meaning as described above.]

[0299] Step (I-1) is typically carried out in a solvent. Examples of solvents used in the reaction include ethers, amides, and mixtures of two or more of them.

[0300] Examples of bases used in reactions include sodium hydride.

[0301] In the reaction, compound (M9) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B6), and the base is usually used in a ratio of 0.5 to 5 moles.

[0302] The reaction time typically ranges from 5 minutes to 72 hours. The reaction temperature typically ranges from -20°C to 100°C.

[0303] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (B7).

[0304] Compound (M9) is a commercially available compound or can be manufactured using known methods.

[0305] Step (I-2) is typically carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more of them.

[0306] Examples of bases used in reactions include organic bases, alkali metal carbonates, alkali metal bicarbonates, and sodium hydride.

[0307] In the reaction, compound (M10) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B7), and the base is usually used in a ratio of 1 to 20 moles.

[0308] The reaction temperature is typically in the range of -20 to 100°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0309] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (A6).

[0310] Compound (M10) is a commercially available compound or can be manufactured using known methods.

[0311] Manufacturing method K

[0312] The compound represented by formula (A7) (hereinafter referred to as compound (A7)) can be manufactured by the following steps: reacting the compound represented by formula (B26) (hereinafter referred to as compound (B26)) with the compound represented by formula (M12) (hereinafter referred to as compound (M12)) in the presence of a base to obtain the compound represented by formula (B9) (hereinafter referred to as step (K-1)); and reacting the compound (B9) with the compound (M10) in the presence of a base (hereinafter referred to as step (K-2)).

[0313] [Chemical Formula 14]

[0314]

[0315] In the formula, R 56 [This symbol indicates tert-butyl or isopentyl; other symbols have the same meaning as described above.]

[0316] Step (K-1) is typically carried out in a solvent. Examples of solvents used in the reaction include ethers, amides, alcohols, and mixtures of two or more of them.

[0317] Examples of bases used in the reaction include sodium hydride, sodium methoxide, sodium ethoxide, potassium tert-butoxide, and other alkali metal alkoxides (hereinafter referred to as alkali metal alkoxides).

[0318] In the reaction, compound (M12) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B6), and the base is usually used in a ratio of 1 to 5 moles.

[0319] The reaction time typically ranges from 5 minutes to 72 hours. The reaction temperature typically ranges from -20°C to 100°C.

[0320] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (B9).

[0321] Compound (M12) is a commercially available compound or can be manufactured using known methods.

[0322] In step (K-2), compound (B9) can be used instead of compound (B7), and the process can be carried out in accordance with step (I-2) of manufacturing method I.

[0323] Manufacturing method L

[0324] The compound represented by formula (A8) (hereinafter referred to as compound (A8)) can be prepared by reacting the compound represented by formula (B10) (hereinafter referred to as compound (B10)) with the compound represented by formula (M13) (hereinafter referred to as compound (M13)) in the presence of a catalyst and a base.

[0325] [Chemical Formula 15]

[0326]

[0327] [In the formula, the symbols represent the same meaning as described above.]

[0328] The reaction can be carried out using compound (M13) instead of compound (B1) and compound (B10) instead of compound (M1), according to manufacturing method A.

[0329] Compound (M13) is a known compound or can be manufactured by known methods.

[0330] Manufacturing method M

[0331] The N oxide of the compound represented by formula (I) can be prepared by reacting the compound represented by formula (I) with an oxidizing agent. The reaction can be carried out according to, for example, the methods described in U.S. Patent Application Publication No. 2018 / 0009778 or International Publication No. 2016 / 121970.

[0332] Reference manufacturing method 1

[0333] Compound (B7) can be manufactured by the following steps: reacting compound (B6) with the compound represented by formula (M11) (hereinafter referred to as compound (M11)) to obtain the compound represented by formula (B8) (hereinafter referred to as step (1-1)); and reacting compound (B8) in the presence of an acid to obtain compound (B7) (hereinafter referred to as step (1-2)).

[0334] [Chemical Formula 16]

[0335]

[0336] [In the formula, the symbols represent the same meaning as described above.]

[0337] Step (1-1) is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, halogenated hydrocarbons, ethers, amides, and mixtures of two or more of them.

[0338] In the reaction, compound (M11) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B6).

[0339] The reaction time typically ranges from 5 minutes to 72 hours. The reaction temperature typically ranges from -20°C to 200°C.

[0340] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (B8).

[0341] Compound (M11) is a commercially available compound or can be manufactured using known methods.

[0342] Steps (1-2) are typically carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water, and mixtures of two or more of these.

[0343] Examples of acids used in the reaction include hydrochloric acid and acetic acid.

[0344] In the reaction, the acid is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B8), and the base is usually used in a ratio of 1 to 20 moles.

[0345] The reaction temperature is typically in the range of -20 to 100°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0346] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (B7).

[0347] Reference manufacturing method 2

[0348] The compound represented by formula (B16) (hereinafter referred to as compound (B16)) can be manufactured by the following steps: reacting the compound represented by formula (B11) (hereinafter referred to as compound (B11)) with the compound represented by formula (M14) (hereinafter referred to as compound (M14)) in the presence of a catalyst and a base to obtain the compound represented by formula (B12) (hereinafter referred to as compound (B12)) (hereinafter referred to as step (2-1)); reacting compound (B12) in the presence of a base to obtain the compound represented by formula (B13) (hereinafter referred to as compound (B13)). The process of reacting compound (B13) with compound (M11) to obtain compound (B14) (hereinafter referred to as compound (B14)) is called process (2-3). The process of reacting compound (B14) with compound (M11) in the presence of an acid to obtain compound (B15) (hereinafter referred to as compound (B15)) is called process (2-4). The process of reacting compound (B15) with compound (M10) in the presence of a base is called process (2-5).

[0349] [Chemical Formula 17]

[0350]

[0351] [In the formula, the symbols represent the same meaning as described above.]

[0352] Step (2-1) is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixtures of two or more of them.

[0353] Examples of palladium catalysts used in the reaction include palladium(II) acetate, Pd2(dba)3, Pd(PPh3)4, and PdCl2(dppf); and copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) trifluoromethanesulfonate (I) benzene complex, copper(I) tetra(acetonitrile) hexafluorophosphate, and copper(I) 2-thiophenecarboxylate.

[0354] Examples of bases used in reactions include organic bases; alkali metal carbonates; alkali metal bicarbonates; alkali metal phosphates such as tripotassium phosphate (hereinafter referred to as alkali metal phosphates); and acetates such as sodium acetate (hereinafter referred to as acetates).

[0355] In the reaction, ligands can be used as needed. Examples of ligands used in the reaction include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl, tri-tert-butylphosphine, 1,2-bis(diphenylphosphino)ethane, pyridine-2-carboxylic acid, (L)-proline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'-dimethylethylenediamine, and N,N-dimethylglycine hydrochloride. When ligands are used in a reaction, they are typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (B11).

[0356] In the reaction, relative to 1 mole of compound (B11), compound (M14) is usually used in a ratio of 0.1 to 10 moles, catalyst is usually used in a ratio of 0.01 to 1 mole, and base is usually used in a ratio of 1 to 10 moles.

[0357] The reaction time typically ranges from 5 minutes to 72 hours. The reaction temperature typically ranges from -20°C to 200°C.

[0358] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (B12).

[0359] Compound (M14) is a known compound or can be manufactured by known methods.

[0360] Step (2-2) is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water, and mixtures of two or more of them.

[0361] Examples of bases used in reactions include alkali metal phosphates and alkali metal alkoxides.

[0362] In the reaction, the base is usually used in a ratio of 1 to 20 moles relative to 1 mole of compound (B12).

[0363] Step (2-3) can be performed by using compound (B13) instead of compound (B6) in accordance with step (1-1) of reference manufacturing method 1.

[0364] Step (2-4) can be performed by using compound (B14) instead of compound (B8) in accordance with step (1-2) of reference manufacturing method 1.

[0365] Step (2-5) can use compound (B15) instead of compound (B7) and be carried out in accordance with step (I-2) of manufacturing method I.

[0366] Reference manufacturing method 3

[0367] The compound represented by formula (B18) (hereinafter referred to as compound (B18)) can be manufactured by the following steps: reacting compound represented by formula (B27) (hereinafter referred to as compound (B27)) with compound (M12) in the presence of a base to obtain compound represented by formula (B17) (hereinafter referred to as step (3-1)); and reacting compound (B17) with compound (M10) in the presence of a base (hereinafter referred to as step (3-2)).

[0368] [Chemical Formula 18]

[0369]

[0370] [In the formula, the symbols represent the same meaning as described above.]

[0371] Step (3-1) can be performed by using compound (B27) instead of compound (B26) and following step (K-1) of manufacturing method K.

[0372] Step (3-2) can use compound (B17) instead of compound (B9) and be carried out in accordance with step (K-2) of manufacturing method K.

[0373] Reference manufacturing method 4

[0374] Compound (B2) can be prepared by reacting compound (B1) with diboronic acid or diboronic ester in the presence of a base and a palladium catalyst.

[0375] [Chemical Formula 19]

[0376]

[0377] [In the formula, the symbols represent the same meaning as described above.]

[0378] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; sulfoxides such as dimethyl sulfoxide (DMSO); nitriles and mixtures of two or more of them.

[0379] Examples of bases used in reactions include organic bases, alkali metal carbonates, alkali metal bicarbonates, acetates, and tripotassium phosphate.

[0380] Examples of palladium catalysts include PdCl2(dppf).

[0381] Examples of diboronic acids or diboronic esters include bis(pinacol)diborane and tetrahydroxydiborane.

[0382] In the reaction, diboronic acid or diboronic ester is typically used in a ratio of 1 to 5 moles relative to 1 mole of compound (B1), base is typically used in a ratio of 1 to 5 moles, and palladium catalyst is typically used in a ratio of 0.01 to 0.5 moles.

[0383] The reaction temperature is usually in the range of 0 to 150°C, and the reaction time is usually in the range of 0.1 to 48 hours.

[0384] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (B2).

[0385] Reference manufacturing method 5

[0386] Compound (B5) can be produced by oxidizing compound (B2).

[0387] [Chemical Formula 20]

[0388]

[0389] [In the formula, the symbols represent the same meaning as described above.]

[0390] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water, and mixtures of two or more of them.

[0391] Examples of oxidizing agents used in the reaction include m-chloroperoxybenzoic acid and aqueous hydrogen peroxide solution.

[0392] When using an aqueous solution of hydrogen peroxide as an oxidant, an alkali can be added as needed.

[0393] Sodium hydroxide and potassium hydroxide are examples of alkalis.

[0394] In the reaction, the oxidant is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (B2).

[0395] When a base is used in a reaction, the base is typically used in a ratio of 0.1 to 5 moles relative to 1 mole of compound (B2).

[0396] The reaction temperature is usually in the range of -20 to 120°C, and the reaction time is usually in the range of 0.1 to 48 hours.

[0397] After the reaction is complete, water and reducing agents such as sodium thiosulfate can be added to the reaction mixture, and extraction can be performed with an organic solvent. Post-processing operations such as drying and concentrating the organic layer can then be carried out to separate the compound (B5).

[0398] Reference manufacturing method 6

[0399] Compound (B5) can be manufactured by the following steps: reacting compound (B19) with diboronic acid or diboronic ester in the presence of a base and a palladium catalyst to obtain compound (B20) (hereinafter referred to as step (6-1)); and reacting compound (B20) with compound (M13) in the presence of a base and a metal catalyst (hereinafter referred to as step (6-2)).

[0400] [Chemical Formula 21]

[0401]

[0402] [In the formula, the symbols represent the same meaning as described above.]

[0403] Step (6-1) can be performed using compound (B19) instead of compound (B1), in accordance with reference manufacturing method 4.

[0404] Compound (B19) is a known compound or can be manufactured by known methods.

[0405] Step (6-2) can use compound (B20) instead of compound (M1) and compound (M13) instead of compound (B1) and be carried out in accordance with manufacturing method A.

[0406] Reference manufacturing method 7

[0407] The compound represented by formula (B21) (hereinafter referred to as compound (B21)) can be prepared by reacting compound (B5) with trifluoroacetic anhydride in the presence of a base.

[0408] [Chemical Formula 22]

[0409]

[0410] [In the formula, the symbols represent the same meaning as described above.]

[0411] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more of them.

[0412] Examples of bases include organic bases.

[0413] In the reaction, trifluoroacetic anhydride is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B5), and the base is usually used in a ratio of 1 to 10 moles.

[0414] The reaction temperature is typically in the range of -20 to 100°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0415] Reference manufacturing method 8

[0416] The compound represented by formula (B22) can be produced by reacting compound (B1) with the compound represented by formula (M15) (hereinafter referred to as compound (M15)).

[0417] [Chemical Formula 23]

[0418]

[0419] In the formula, R 57 This indicates methyl or ethyl; other symbols have the same meaning as described above.

[0420] The reaction can be carried out in accordance with, for example, the method described in International Publication No. 2016 / 123253.

[0421] Compound (M15) is a commercially available compound or can be manufactured using known methods.

[0422] Reference manufacturing method 9

[0423] Compound (B4) can be produced by reacting compound (B3) with a hydroxylamine or its salt.

[0424] [Chemical Formula 24]

[0425]

[0426] [In the formula, the symbols represent the same meaning as described above.]

[0427] Examples of salts of hydroxylamine include hydrochloride and sulfate.

[0428] The reaction can be carried out using hydroxylamine or its salt instead of compound (M4) according to manufacturing method D.

[0429] Reference manufacturing method 10

[0430] The compound represented by formula (B23) can be prepared by reacting compound (B1) with N-formylsaccharin in the presence of a palladium catalyst, a ligand, triethylsilane and a base.

[0431] [Chemical Formula 25]

[0432]

[0433] [In the formula, the symbols represent the same meaning as described above.]

[0434] The reaction can be carried out according to the methods described in Angew. Chem. Int. Ed., 2013, 52, 8611-8615, etc.

[0435] Reference manufacturing method 11

[0436] The compound represented by formula (B24) can be prepared by reacting compound (B27) with compound (M1) in the presence of a palladium catalyst and a base.

[0437] [Chemical Formula 26]

[0438]

[0439] [In the formula, the symbols represent the same meaning as described above.]

[0440] The reaction can be carried out using compound (B27) instead of compound (B1) according to manufacturing method A.

[0441] Reference manufacturing method 12

[0442] The compound represented by formula (B25) can be prepared by reacting compound (B27) with compound (M3) in the presence of a metal catalyst and a base.

[0443] [Chemical Formula 27]

[0444]

[0445] [In the formula, the symbols represent the same meaning as described above.]

[0446] The reaction can be carried out using compound (B27) instead of compound (B1) according to manufacturing method C.

[0447] The compounds of the present invention may be used in combination or in combination with one or more components (hereinafter referred to as the component) selected from the group consisting of group (a), group (b), group (c) and group (d) below.

[0448] The aforementioned combination or use refers to using the compound of the present invention and the ingredient simultaneously, separately, or at intervals.

[0449] When the compound of the present invention and the ingredient are used simultaneously, the compound of the present invention and the ingredient may be contained in separate formulations or in the same formulation.

[0450] One aspect of the present invention is a composition comprising one or more components selected from groups (a), (b), (c) and (d) of the present invention (i.e., the component itself) and the compound of the present invention (hereinafter referred to as composition A).

[0451] Group (a) comprises acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABA-gated chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormones, multisite inhibitors, string organ TRPV channel modulators, mite growth inhibitors, and insect midgut membranes derived from microorganisms. This group comprises disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncoupling agents, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin-based insecticides), chitin synthesis inhibitors, ecdysone inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial complex I, II, III, and IV electron transport inhibitors, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ranotin receptor modulators (e.g., diamide-based insecticides), string mechanism modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients. These ingredients are described according to their IRAC-based mechanisms of action.

[0452] Group (b) comprises nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid and protein synthesis inhibitors (e.g., aniline-pyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., triazole-based DMI fungicides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-point contact active fungicides, microbial fungicides, and other fungicidal active ingredients. These ingredients are described according to the classification based on FRAC-based mechanisms of action.

[0453] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0454] Group (d) is the group containing the repellent component.

[0455] The following describes examples of combinations of this component with the compounds of the present invention. For example, alanycarb + SX refers to the combination of alanycarb and SX.

[0456] It should be noted that the abbreviation SX refers to any one of the compounds of the present invention selected from the compound groups SX1 to SX259 described in the examples. Furthermore, all the ingredients described below are known ingredients and can be obtained from commercially available formulations or manufactured by known methods. If the ingredient is a microorganism, it can also be obtained from a microbial depository. It should be noted that the numbers in parentheses represent CAS RN (registered trademark).

[0457] The combination of the component of group (a) above with the compounds of the present invention:

[0458] Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acridine lactate + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide Phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus Angulatus + SX, Bendiocorb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Benximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, Beta-cypermethrin + SX, Bifenazate + SX, Bifenthrin + SX, Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Borax + SX, Boric acid acid) + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX,Carbosulfan + SX, Cartap hydrochloride + SX, Cartap + SX, Chinomethionat + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, Chloropicrin + SX, Chlorpyrifos + SX, Chlorpyrifos-methyl + SX, Chlorafenozide + SX, Clofentezine + SX, Clothianidin + SX, Concanavalin A A) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX Cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, cyproflanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, diclomethasone + SX, dicofol + SXDicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate + SX, disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol + SX), doramectin + SX, dried leaves of Dryopteris Filix-mas)+SX, Emamectin-benzoate+SX, Empenthrin+SX, Endosulfan+SX, EPN (O-ethyl O-(4-nitrophenyl)phenylphosphonothioate)+SX, Epsilon-metofluthrin+SX, Epsilon-momfluorothrin+SX, Esfenvalerate+SX, Ethiofencarb+SX, Ethion+SX, Ethiprole+SX, Ethoprophos+SX, Etofenprox+SX, Etoxazole+SX, Extract of Artemisia absinthium+SX, Neem extract Extracts of Azadirachta indica (SX), Cassia nigricans (SX), Butterfly pea (SX), Symphonytum officinale (SX), Cheminaria ambrosioides (SX), Tanacetum vulgare (SX)Extracts of Urtica dioica + SX, extracts of Viscum album + SX, famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatin oxide)+SX, fenitrothion+SX, fenmezoditiaz+SX, fenobucarb+SX, fenoxycarb+SX, fenpropathrin+SX, fenpyroximate+SX, fenthion+SX, fenvalerate+SX, fipronil+SX, fometoquin+SX, flonicamid+SX, fluacrypyrim+SX, fluazaindolizine+SX, fluazuron+SX, flubendiamide+SX, fluchlordiniliprole+SX, flucycloxuron+SX, flucypermethrin Ester (flucythrinate) + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + 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 (GS-omega / kappa HXTX-Hv1a peptide) + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SXHeptenophos +SX, hexaflumuron +SX, hexythiazox +SX, potassium salt of hop beta acid +SX, hydramethylnon +SX, hydroprene +SX, imicyafos +SX, imidacloprid +SX, imidaclothiz +SX, imiprothrin +SX, indazapyroxamet +SX, indoxacarb +SX, isocycloseram +SX, isofenphos +SX, isoprocarb +SX, isopropyl O-(methoxyaminothiophosphoryl)salicylic acid isopropyl ( 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 (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 + SXMetoxadiazone + SX, Mevinphos + SX, Milbemectin + SX, Milbemycin oxime + SX, Momfluorothrin + SX, Monocrotophos + SX, Moxidectin + SX, Naled + SX, Nicofluprole + SX, Nicotine + SX, Nicotine-sulfate + SX, Nitenpyram + SX, Novaluron + SX, Noviflumuron + SX, Chenopodium anthelminticum seed oil Chenopodium anthelminticum + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosphazene Phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate glycol alginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SXPyrifluquinazone + 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 Metaborate + SX, Spidoxamat + SX, Spinetoram + SX, Spinosad + SX, Spirodiclofen + SX, Spiroomesifen + SX, Spiropidion + SX, Spiotetramat + SX, Sulfuramid + SX, Sulfotep + SX, Sulfoxaflor + SX, Sulfur + SX, Sulfurylfluoride + SX, Tartar emetic)+SX, tau-fluvalinate+SX, tebufenozide+SX, tebufenpyrad+SX, tebupirimfos+SX, teflubenzuron+SX, tefluthrin+SX, temephos+SX, terbufos+SX, terpene constituents of the extract of chenopodium ambrosioides near ambrosioides+SX, tetrachlorantraniliprole+SX, tetrachlorvinphos+SX, tetradifon+SX, tetramethrin+SX, tetramethylfluthrin+SX, tetratraniliprole+SXTheta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-monosodium + SX, tioxazafen + SX, tolfenpyrad + SX, tetracycline + SX, thiocyclam ... Tralomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, tyclopyrazoflor + SX, vamidothion + SX, wood extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide phosphide)+SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothioheterobutane-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)propionamide (1118626-57-5)+SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)thionyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5)+SX,(2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)thionyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6)+SX、N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9)+SX、N- [3-Chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propionamide (2396747-83-2)+SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3)+SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0)+SX, N-({ 2-Fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidine-1-yl]phenyl}methyl)cyclopropanecarboxamide +SX, 7-Fluoro-N-[1-(methylthioalkyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide +SX, 7-Fluoro-N-[1-(methanethionyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide +SX, 7-Fluoro-N-[1-( [Methanesulfonyl]-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide +SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide +SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyridolo[2,3-b][1,4]oxazazepine-10-one (2607927-97-7) +SX, Cry1Ab (BT) protein of BT crop BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX, BT crop protein Cry1Fa + SX, BT crop protein Cry1A.105 + SX, BT crop protein Cry2Ab + SX, BT crop protein Vip3A + SX.BT crop protein mCry3A + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 + SX, Tea leafroller granulovirus strain BV-0001 + SX, Soybean noctuid moth nucleopolyhedrovirus (Anticarsiagemmatalis mNPV) + SX, Alfalfa silver-striped noctuid moth nucleopolyhedrovirus (Autographa californica mNPV) + SX, Codling moth granulovirus strain V15 + SX, Codling moth granulovirus strain V22 + SX. The following viruses were detected: strain V22) + SX, Cryptophorbia leucotreta GV + SX, Dendrolimus punctatus cypovirus + 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, and Neodiprion pine sawfly NPV + SX. Lecontei NPV+SX, Neodiprion sertifer NPV+SX, Nosema locustae+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX,Indian meal moth granulovirus (Plodia interpunctella GV) + SX, beet armyworm nucleopolyhedrovirus (Spodoptera exigua mNPV) + SX, sea grebe moth nucleopolyhedrovirus (Spodoptera litura NPV) + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus species AQ175 (Bacillus sp. strain) AQ175)+SX, Bacillus sp. strain AQ177+SX, Bacillus sp. strain AQ178+SX, Bacillus sphaericus strain 2362 serotype H5a5b+SX, Bacillus sphaericus strain ABTS1743+SX, Bacillus thuringiensis strain AQ52+SX, Bacillus thuringiensis strain BD#32+SX, Bacillus thuringiensis strain CR-371 CR-371)+SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52+SX,Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain NB200+SX, Bacillus thuringiensis subsp. Aizawai serotype strain H-7+SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351+SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 BMP123)+SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306+SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348+SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841+SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19+SX, Bacillus thuringiensis subsp. Kurstaki strain F810 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 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. israelensis serotype strain H-14+SX, Bacillus thuringiensis var. japonensis strain buibui+SX, Bacillus thuringiensis var. san diego strain M-7 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, novel heat-inactivated bacterium A396 + SX, active purple bacterium PRAA4-1T strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Decylaria 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 microsporum BIPESCO strain 5 / F52 (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 nishizawaestrain Pn1+SX, Pasteuria penetrans+SX, Pasteuria usgae+SX, Pasteuria thornei+SX, Serratia entomophila+SX, Verticillium chlamydosporium+SX, Verticillium lecani NCIM1312+SX strain NCIM1312) + SX, Wolbachia pipientis + SX.

[0459] The combination of this component of group (b) above with the compounds of the present invention:

[0460] Acibenzolar-S-methyl + SX, Aldimorph + SX, Ametoctradin + SX, Aminopyrifen + SX, Amisulbrom + SX, Anilazine + SX, Azaconazole + SX, Azoxystrobin + SX, Basic copper sulfate 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 The following are listed: mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionat + SX, chitin + SX, chloroinconazide + SX, chloroneb + ​​SX, chlorothalonil + SX, chlozolinate + SX, colletochlorin B+SX, copper(II)acetate+SX, copper(II)hydroxide+SX, basic copper chloride+SX, copper(II)sulfate+SX, coumoxystrobin+SX, cyazofamid+SX, cyflufenamid+SXCymoxanil + SX, Cyproconazole + SX, Cyprodinil + SX, Dichlobentiazox + SX, Dichlofluanid + SX, Diclomezine + SX, Dicloran + SX, Diethofencarb + SX, Difenoconazole + SX, Diflumetorim + SX, Dimethachlone + S X, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogen phosphite + SX, dipymetitrone + SX, dithianon + SX, dodecylbenzenesulphonic bis(ethylenediamine)copper(II) complex salt acid bisethylenediamine copper(II)salt)+SX, dodemorph+SX, dodine+SX, edifenphos+SX, enoxastrobin+SX, epoxiconazole+SX, etaconazole+SX, ethaboxam+SX, ethirimol+SX, etridiazole+SX, extract of Melaleuca alternifolia+SX, extract of Reynoutria sachalinensis+SX, extract of the cotyledons of lupine plantlets ("BLAD")+SX, extract of Allium sativum+SX, extract of Equisetum arvense+SX, extract of Nasturtium Tropaeolummajus)+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, Fentin acetate + SX, Fentin chloride + SX, Fentin hydroxide + SX Hydroxide + SX, Ferbam + SX, Ferimzone + SX, Florylpicoxamid + SX, Fluazinam + SX, Flubeneteram + SX, Fludioxonil + SX, Flufenoxadiazam + SX, Flufenoxystrobin + SX, Fluindapyr + SX, Flumetylsulforim + SX, Flumorph + SX, Fluopicolide + SX, Fluopyram + SX, Fluopimomide + SX, Fluoxapiprolin + SX Fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetyl-aluminium + SX, furidazole + SX, furalaxyl + SX, furamettapyr + SX, guazatine + SXHexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX, isofetamid + SX, isoflucypram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, leaves and bark of oak trees ofQuercus)+SX, mancozeb+SX, mandestrobin+SX, mandipropamid+SX, maneb+SX, mefentrifluconazole+SX, mepanipyrim+SX, mepronil+SX, meptyldinocap+SX, metalaxyl+SX, metalaxyl-M+SX, metarylpicoxamid+SX, metcon azole) + SX, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofuronamide + SX, orysastrobin + SX, oxadixyl + SX,Oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiophanate + SX, phenamacril + SX, phosphorous acid acid) + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, potassium hydrogencarbonate + SX, potassium dihydrogen phosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridachlometyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SXPyriofenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, quinconazole + SX, quinofumelin + SX, quinoxyfen + SX, quintozene + SX, saponins of Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX, simeconazole + SX, sodium bicarbonate Hydrogencarbonate + SX, Spiroxamine + SX, Streptomycin + SX, Sulfur + SX, Tebuconazole + SX, Tebufloquin + SX, Teclofthalam + SX, Tecnazene + SX, Terbinafine + SX, Tetraconazole + SX, Thiabendazole + SX, Thifluzamide + SX, Thioprazan + SX, Thioprazan-methyl + SX, Thiram + SX, Thymol + SX, Tiadinil + SX , tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, trilopyricarb + SX, tricyclazole + SX, tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, triforine + SX, triticonazole + SX, validamycin + SX, valifenalate + SXVinclozolin + SX, Yellow Mustard Powder + SX, Thiazole Zinc + 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-methylformamidin (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidin (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N -Ethyl-N-methylformamidinium (1052688-31-9)+SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylformamidinium (2055589-28-9)+SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidinium (2055756-21-1)+SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformamidinium (2062599-39-5)+SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl] [5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidin (1817828-69-5)+SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (1362477-26-6)+SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazolin (1257056-97-5)+SX, (2Z)-3-amino-2-cyano-3- Ethyl phenyl acrylate (39491-78-6)+SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridine-2-amine (1446247-98-8)+SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4)+SX, (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2)+SX,(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3)+SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6)+SX, (1R,2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4)+SX, (1S, 2R,5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5)+SX, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylic acid methyl ester (1791398-02-1)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0)+SX, 1-(2,4- (difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxylon (2018316-13-5)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxylon (2018317-25-2)+SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- Triazol-1-yl)propane-2-ol (2082661-43-4)+SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propane-2-ol (2082660-27-1)+SX, ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8)+SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridin-3-carboxamide (1616239-21-4)+SX,2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1847460-02-9)+SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1847460-05-2)+SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-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 (1445331-27-0)+SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide -[[2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl]amino]-6-methylpyrimidine](1445331-54-3)+SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine](1605340-92-8)+SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide](2132414-04-9)+SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide](2132414-00-5)+SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-[3-yl]phenyl}methyl)isoxazolin-3-one (2098918-25-1)+SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one (2098918-26-2)+SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide+SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide+SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide+SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide+SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide+SX, [4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)urea +SX, N'-ethyl-N-methoxy-N-(4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)urea +SX, N,N'-dimethoxy-N-(4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)urea +SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) +SX,N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(4-bromo-7-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromoindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]- L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester +SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester) N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate)+SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropionic acid +SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide +SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionic acid +SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionic acid +SX,3,3,3-Trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, 3,3,3-Trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, 3,3,3-Trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butyramide + SX, N-methoxy-N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butyramide + SX, N-methoxy-N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butyramide + SX, )-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N,N-diethyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidone-2-one+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one+SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one+SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azacycloheptane-2-one+SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azacycloheptane-2-one+SX, 2,4-Oxadiazol-3-yl]phenyl}methyl)pyrrolidone-2-one+SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidone-2-one+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylic acid ethyl ester+SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide+SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide+SX,N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine +SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide +SX, 2-[2-chloro-4-(4-chlorophenoxy)benzamide Methyl 2-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate +SX, ethyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate +SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate +SX, methyl 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX 2,2-Difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide +SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxynitrile +SX, 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester +SX, 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester +SX, 6-chloro- 3-(3-Cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide +SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide +SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX,2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3,4]oct-1-yl)-5-methylthiazol-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazol-4-carboxamide +SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-[(2-methylpropionyl)(2,6-difluoro... [Pyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-[1-] (6-Chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl) Cyclopropyl]oxy}pyrimidine +SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine +SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine +SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine +SX,3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, Agrobacterium radiobactor strain K1026 1026)+SX, Agrobacterium radiobactor strain K84+SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo 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 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 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 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 The following strains of bacteria were tested: 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, and Candida hydrolytica. 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 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 CL145A)+SX, Pseudomonas fluorescens strain G7090+SX, Pseudomonas sp. strain CAB-02+SX, Pseudomonas syringae strain 742RS+SX,*Pseudomonas syringae* strain MA-4 + SX, *Pseudozymaflocculosa* strain PF-A22UL + SX, *Pseudomonas rhodesiaestrain 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. strains WYEC108+SX, *Talaromyces flavus* strain SAY-Y-94-01+SX, *Talaromyces flavus* strain V117b+SX, *Trichoderma asperellum* strain ICC012+SX, *Trichoderma asperellum* strain SKT-1+SX, *Trichoderma asperellum* strain T25+SX, *Trichoderma asperellum* strain T34+SX, *Trichoderma asperellum* strain TV1+SX, *Trichoderma atroviride* strain CNCM1-1237 1-1237)+SX, Trichoderma atrovirides strain LC52+SX, Trichoderma atrovirides strain IMI 206040+SX, Trichoderma atrovirides 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 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 TH35)+SX, Trichoderma polysporum strain IMI206039+SX, Trichoderma stromatomaticum+SX, Trichoderma virens strain G-41+SX,Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovora paradoxus strain CGF4526 + SX, Harpin protein + SX.

[0461] The combination of the component of group (c) above with the compounds of the present invention:

[0462] 1-Methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) Acid + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloridechloride) + SX, cloprop + SX, cyanamide + SX, cyclanilide + SX, daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, gibberellin A A) + SX, Gibberellin A3 + SX, Inabenfide + SX, Kinetin + SX, Lipochitooligosaccharide SP104 + SX, Maleic hydrazide + SX, Mefluidide + SX, Mepiquat-chloride + SX, Oxidized glutathione + SX, Paclobutrazol + SX, Pendimethalin + SX, Prohexadione-calcium + SX, Prohydrojasmon + SX, Pyraflufen-ethyl + SX, Sintofen + SX, Sodium 1-naphthaleneacetate + SX, Sodium 1-naphthaleneacetate + SX, Sodium cyanate cyanate)+SX, thidiazuron+SX, triapenthenol+SX, tribufos+SX, trinexapac-ethyl+SX, uniconazole-P+SX, 2-(naphthalen-1-yl)acetamide+SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid+SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate+SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propane-1-ol+SX, Claroideoglomusetunicatum)+SX, Claroideoglomus claroideum+SX, Funneliformis mosseae+SX, Giaspora margarita+SX, Giaspora rosea+SX, Glomus aggregatum+SX, Glomus deserticola+SX, Glomus monosporum+SX, Paraglomus brasillianum+SX, Rhizophagus clarus+SX, Rhizophagus intraradices RTI-801 strain+SX, Rhizophagus irregularis DAOM Azospirillum 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 strain + SX, Bradyrhizobium japonicum TA-11 strain + SX, Bradyrhizobium japonicum USDA 110 strain + SX, Bradyrhizobium liaoningense strain + SX, Bradyrhizobium lupini strain + SX, Delftia acidovorans RAY209 strain + SX, Mesorhizobium ciceri strain + SX, MesorhizobiumRhizobium 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 falfya+SX meliloti)+SX, Zucchini Yellow Mosaik Virus weak strain+SX.

[0463] The combination of the component of group (d) above with the compounds of the present invention:

[0464] Anthraquinone + SX, DEET + SX, Icaridin + SX.

[0465] The ratio of the compound to the component of this invention is not particularly limited, but examples of weight ratios (compound of this invention: component of this invention) of 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc.

[0466] The compounds of this invention are effective against harmful organisms. Examples of harmful organisms include plant pathogenic microorganisms, harmful insects, harmful mites and other harmful arthropods, harmful nematodes, and harmful mollusks.

[0467] The compounds of this invention can prevent and control plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, phytomyxea, and bacteria. Examples of fungi include, for instance, Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specifically, examples include, for instance, the following. The scientific names of the plant pathogenic microorganisms causing each disease are shown in parentheses.

[0468] Rice diseases: Blight (Pyricularia oryzae), Sesame leaf blight (Cochliobolus miyabeanus), Sheath blight (Rhizoctonia solani), Bakanae disease (Gibberella fujikuroi), Yellowing and stunting disease (Sclerophthora macrospora), Pseudo-rice blast and panicle blight (Epicoccum nigrum), Seedling blight (Trichodermaviride, Rhizopus oryzae), False sheath blight (Waiteacircinata), Ceratobasidium setariae, Thanatephorus cucumeris);

[0469] Wheat diseases: Powdery mildew (Blumeria graminis), Fusarium head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Red rust (Puccinia recondita), Red snow rot (Microdochium majus), Sclerotinia sclerotium rot (Typhula incarnata, Typhula ishikariensis), Loose smut (Ustilago maydis). Tritici), smut (Tilletiacaries, Tilletia controversa), eye spot (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), glume blight (Stagonospora nodorum), yellow spot (Pyrenophoratritici-repentis), seedling damping-off (Rhizoctonia solani), damping-off (Gaeumannomyces graminis), Pyricularia graminis-tritici;

[0470] Barley diseases: Powdery mildew (Blumeria graminis), Fusarium head blight (Fusarium graminis, Fusarium oatum, Fusarium graminis, Micrococcus spp.), Yellow rust (Stripe rust), Black rust (Stem rust), Stripe rust (Puccinia hordei), Smut (Ustilago nuda), Cloud blight (Rhynchosporium secalis), Net blight (Pyrenophora teres), Leaf spot (Cochliobolus sativus), Leaf stripe (Pyrenophora graminea), Ramularia collo-cygni, Damping-off caused by Rhizoctonia solani.

[0471] Corn diseases: Rust (Puccinia sorghi), Southern rust (Puccinia polysora), Large leaf spot (Setosphaeria turcica), Tropical rust (Physopella zeae), Sesame leaf blight (Cochliobolus heterostrophus), Anthracnose (Colletotrichum graminicola), Gray leaf spot (Cercospora zeae-maydis), Brown spot (Kabatiella zeae), Phaeosphaeria maydis, Stenocarpella maydis, Stenocarpellamacrospora, Stem rot (Fusarium graminii). verticilioides), Colletotrichum graminicola), Ustilago maydis (corn smut), Physoderma maydis (corn stalk rot), Phyllachora maydis (corn black spore causal agent);

[0472] Cotton diseases: Anthracnose (Colletotrichum gossypii), White mold (Ramularia areola), Black spot (Alternaria macrospora, Alternaria gossypii), Root black rot (Thielaviopsis basicola).

[0473] Coffee diseases: Rust (cafe rust fungus (Hemileia vastatrix)), leaf spot (Cercospora coffeicola));

[0474] Diseases of rapeseed: Sclerotinia sclerotiorum, Alternaria brassicae, Phona lingam, Pyrenopeziza brassicae;

[0475] Sugarcane diseases: Rust (Puccinia melanocephela, Pucciniakuehnii), Smut (Ustilagoscitaminea);

[0476] Sunflower diseases: Rust (Puccinia helianthi), downy mildew (Plasmopara halstedii);

[0477] Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), penicillium rot (Penicillium digitatum), penicillium disease (Penicillium italicum), blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillosis (Aspergillus niger);

[0478] Apple diseases: Blossom rot (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria alternata (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), blight (Phytophthora cactorum), red spot (Gymnosporangium). juniperi-virginianae), Gymnosporangium yamadae);

[0479] Pear diseases: Black spot (Venturia nashicola, Venturiapirina), Black spot (Alternaria alternata Japanese pearpathotype), Gymnosporangium haraeanum (Gymnosporangium haraeanum);

[0480] Peach diseases: Gray spot (Monilinia fructicola), Black spot (Cladosporium carpophilum), Brown spot (Phomopsis sp.), Leaf curl (Taphrina deformans);

[0481] 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 (Plasmoparaviticola);

[0482] Diseases of persimmon: Anthracnose (Gloeosporium kaki, Colletotrichum acutatum) and leaf spot (Cercospora kaki, Mycosphaerella nawae));

[0483] Fig diseases: Rust (Phakopsora nishidana)

[0484] Diseases of gourds: Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), Gynostemma pentaphyllum (Didymella bryoniae), Brown spot (Corynespora cassiicola), Fusarium wilt (Fusarium oxysporum), Downy mildew (Pseudoperonospora cubensis), Phytophthora capsici (Phytophthora capsici), Damping-off (Pythium sp.).

[0485] Tomato diseases: Ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), anthracnose (Pseudocercospora fuligena), blight (Phytophthora infestans), powdery mildew (Leveillula taurica);

[0486] Eggplant diseases: Brown spot (Phomopsis vexans) and powdery mildew (Erysiphe cichoracearum);

[0487] Diseases of cruciferous vegetables: Black spot (Alternaria japonica), White spot (Cercosporella brassicae), Clubroot (Plasmodiophorabrassicae), Downy mildew (Peronospora parasitica), White rust (Albugocandida).

[0488] Diseases of scallions: Rust (from Puccinia allii, a fungus that causes rust onion stems);

[0489] Soybean diseases: Purple blotch (Cercospora kikuchii), Black rot (Elsinoe glycines), Black spot (Diaporthe phaseolorum var. sojae), Rust (Phakopsora pachyrhizi), Brown ring rot (Corynespora cassiicola), Anthracnose (Colletotrichum glycines, Colletotrichum truncatum), Damping-off (Rhizoctonia solani), Brown spot (Septoria glycines), Spot disease (Cercospora sojina), Sclerotinia rot (Sclerotinia sclerotiorum). sclerotiorum), powdery mildew (Microsphaeradiffusa), stem blight (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death syndrome (Fusarium virguliforme), red crown rot (Calonectria ilicicola), Diaporthe / Phomopsis complex (Diaporthe longicolla);

[0490] Diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular leaf spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), and root rot (Fusarium solani).

[0491] Peanut diseases: Black spot (Cercospora personata) , Brown spot (Cercospora arachidicola) , White rot (Sclerotium rolfsii) , Red crown rot (Calonectria ilicicola) ;

[0492] Pea diseases: powdery mildew (Erysiphe pisi) and root rot (Fusarium solani).

[0493] Potato diseases: Early blight (Alternaria solani)), blight (Phytophthora infestans)), red 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);

[0494] Strawberry diseases: Powdery mildew (Sphaerotheca humuli);

[0495] Tea diseases: Net cake disease (Exobasidium reticulatum), white spot disease (Elsinoe leucospila), gray blight (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis);

[0496] Tobacco diseases: Red spot disease (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), blight (Phytophthoranicotianae);

[0497] Diseases of sugar beets: Brown spot (Cercospora beticola)), Leaf blight (Thanatephorus cucumeris)), Root rot (Thanatephorus cucumeris)), Black root rot (Aphanomyces cochlioides)), Rust (Uromyces betae);

[0498] Diseases of roses: Black spot (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa);

[0499] Chrysanthemum diseases: Brown spot (Septoria chrysanthemi-indici) and white rust (Puccinia horiana).

[0500] Onion diseases: Botrytis leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa, Botrytis allii, Botrytis squamosa);

[0501] Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia sclerotiorum, black rot (Sclerotium cepivorum), seedling blight (Pythium aphanermatum, Pythium irregulare, Pythium ultimum);

[0502] Radish diseases: Black spot (Alternaria brassicicola);

[0503] Diseases of turfgrass: Coin spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), and Pythium wilt (Pythium apopandermatum);

[0504] Banana diseases: Banana leaf spot (Sigatoka disease) (Mycosphaerella fijiensis, Mycosphaerella musicola));

[0505] Diseases of lentils: Ascochyta (Ascochyta lentis);

[0506] Chickpea diseases: Ascochyta rabiei (blight);

[0507] Diseases of bell peppers: Anthracnose (Colletotrichum scovillei);

[0508] Mango diseases: Anthracnose (Colletotrichum acutatum);

[0509] Fruit tree diseases: white root rot (Rosellinia necatrix) and purple root rot (Helicobasidium mompa);

[0510] Post-harvest diseases of fruits such as apples and pears: Mucor rot diseases (Mucorpiriformis);

[0511] Seed diseases or diseases in the early stages of growth caused by fungi such as Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thieviopsis, Rhizopus, Mucor, Corticium, Phona, Rhizoctonia, and Diplodia;

[0512] Viral diseases: Giant vein disease of lettuce mediated by Olpidium brassicae; and various viral diseases of crops mediated by Polymyxa species (e.g., Polymyxa betae and Polymyxa graminis).

[0513] Diseases caused by bacteria: Rice bacterial damping-off (Burkholderia plantarii), rice inner glume browning (Pantoea ananatis), rice bacterial leaf blight (Xanthomonas oryzae pv. oryzae.), cucumber bacterial angular leaf spot (Pseudomonas syringaepv. lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces cabbiei), and corn inner wilt (Clavibacter). Crown gall of grapes, olives, peaches, etc. (Xylella fastidiosa) and root nodule disease of Rosaceae plants such as apples, peaches, cherries, etc. (Agrobacterium tumefaciens)

[0514] Examples of harmful arthropods, harmful nematodes, and harmful mollusks include the following.

[0515] Hemiptera: Planthoppers such as *Laodelphax striatellus*, *Nilaparvatalugens*, *Sogatella furcifera*, *Peregrinus maidis*, *Javesella pellucida*, *Perkinsiella saccharicida*, and *Tagosodesorizicolus*; Leafhoppers such as *Nephotettix cincticeps*, *Nephotettix virescens*, *Nephotettix nigropictus*, *Recilia dorsalis*, *Empoasca onukii*, *Empoascafabae*, *Dalbulus maidis*, and *Cofana*. Leafhoppers include species such as *Spectra* and *Amrasca biguttula biguttula* (Cicadellidae); leafhoppers include species such as *Philaenus spumarius* (Aphrophoridae); and leafhoppers include species such as *Mahanarva posticata* and *Mahanarva fimbriolata* (Cercopidae).Beet aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), apple aphid (Aphis pomi), spiraecola aphid (Aphis spiraecola), peach aphid (Myzus persicae), plum aphid (Brachycaudus helichrysi), cabbage aphid (Brevicorynebrassicae), rose apple aphid (Dysaphis plantaginea), cabbage aphid (Lipaphis erysimi), potato aphid (Macrosiphum euphorbiae), eggplant aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), cereal aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphummaidis), orange aphid (Toxoptera citricida), peach aphid (Hyalopterus pruni), sorghum aphid (Melanaphis) Aphids include sacchari, Tetraneura nigriabdominalis, Ceratovacuna lanigera, Eriosoma lanigerum, and Sitobionavenae.

[0516] The following aphids belong to the Phyllostachydae family: grape phylloxera (Daktulosphaira vitifoliae), walnut phylloxera (Phylloxeradevastatrix), walnut leaf phylloxera (Phylloxera notabilis), and southern walnut leaf phylloxera (Phylloxera russelae); hemlock ball aphids (Adelges tsugae), fir ball aphid (Adelges piceae), and fir ball aphid (Aphrastasia pectinatae); rice black bug (Scotinophara lurida), Malayan rice black bug (Scotinophara coarctata), black-bearded green rice (Nezaraantennata), northern two-spotted bug (Eysarcoris aeneus), large-spined white-spotted bug (Eysarcoris lewisi), and broad-spotted bug (Eysarcoris). The species include the following: * *Ventralis*, *Eysarcoris annamita*, *Halyomorpha halys*, *Nezara viridula*, *Euschistus heros*, *Piezodorus guildinii*, *Oebalus pugnax*, and *Dichelops melacanthus* (Pentatomidae); *Scaptocoris castanea* and other soil bugs (Cydnidae); *Riptortus clavatus*, *Leptocorisa chinensis*, and *Leptocorisa acuta* (Alydidae); and *Cletus* (rice thorn bug). The family Coreidae includes species such as *punctiger* and *Leptoglossus australis*; the family Lygaeidae includes species such as *Cavelerius saccharivorus*, *Togohemipterus*, and *Blissus leucopterus*; and the family Miridae includes species such as *Trigonotylus caelestialium*, *Stenotus rubrovittatus*, *Stenodema calcarata*, and *Lygus lineolaris*.The whitefly species include those belonging to the family Aleyrodidae, such as *Trialeurodes vaporariorum*, *Bemisia tabaci*, *Dialeurodescitri*, *Aleurocanthus spiniferus*, *Aleurocanthus cameelliae*, and *Pealius euryae*; the scale insects including *Abgrallaspis cyanophylli*, *Aonidiella aurantii*, *Diaspidiotus perniciosus*, *Pseudaulacaspis pentagona*, *Unaspis yanonensis*, and *Unaspis citri*; and the scale insect species *Ceroplastes*. Scale insects include: Coccidae (such as *Rubens*); Margarodidae (such as *Icerya purchasi* and *Icerya seychellarum*); Pseudococcidae (such as *Phenacoccus solani*, *Phenacoccus sonopsis*, *Planococcus kraunhiae*, *Pseudococcus comstocki*, *Planococcus citri*, *Pseudococcus calceolariae*, *Pseudococcus longispinus*, and *Brevennia rehi*); Diaphorina citri and Trioza. Psyllids include species such as *Cacopsylla pyrisuga*, *Cacopsylla chinensis*, *Bactericera cockerelli*, and *Cacopsylla pyricola*; and lace bugs include species such as *Corythucha ciliata*, *Corythucha marmorata*, *Stephanitis nashi*, and *Stephanitis pyrioides*.The family Cimicidae includes temperate bedbugs (Cimex lectularius) and tropical bedbugs (Cimex hemipterus); the family Cicadidae includes giant cicadas (Quesadagigas); and the family Reduviidae includes harassing kissing bugs (Triatoma infestans), red-banded kissing bugs (Triatoma rubrofasciata), two-part kissing bugs (Triatoma dimidiata), and long red kissing bugs (Rhodonius prolixus).

[0517] Lepidoptera: Rice stem borer (Chilo suppressalis), Taiwan rice stem borer (Chilo polychrysus), rice white stem borer (Scirpophaga innotata), rice stem borer (Scirpophaga incertulas), Rupela albina, rice leaf roller (Cnaphalocrocis medinalis), broad-striped leaf roller (Marasmia patnalis), rice leaf roller (Marasmia exigua), cotton leaf roller (Notarcha derogata), Asian corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), cabbage leaf borer (Hellulaundalis), grape leaf cutter moth (Herpetogramma) Grass moths (Crambidae): * *Luctuosale*, *Parapedia siateterrellus*, *Nymphuladepunctalis*, *Diatraea saccharalis*, *Leucinodes orbonalis*, etc.; Moths (Pyralidae): *Elasmopalpus lignosellus*, *Plodia interpunctella*, *Euzophera batangensis*, *Cadra cautella*, etc.; Lobelia spodoptera litura, *Spodoptera exigua*, armyworm (*Mythimna separata*), cabbage looper (*Mamestrabrassicae*), Chinese tallow leafminer (*Sesamia inferens*), *Spodoptera* (*Spodoptera*). The following are listed: *Spodoptera mauritia*, *Naranga aenescens*, *Spodoptera frugiperda*, *Spodoptera exempta*, *Spodoptera cosmioides*, *Spodoptera eridania*, *Agrotis ipsilon*, *Autographa nigrisigna*, *Plusiafestucae*, *Chrysodeixis includens*, and *Trichoplusia spp.*The species include: *Heliothis virescens* (tobacco bud moth), *Helicoverpa armigera* (cotton bollworm), *Helicoverpa zea* (grain bollworm), *Anticarsia gemmatalis* (bean bollworm), *Alabama argillacea* (cotton leaf moth), and *Hydraecia immanis* (hop vine borer), belonging to the family Noctuidae; *Pieris rapae* (cabbage white butterfly), belonging to the family Pieridae; *Grapholita molesta* (pear fruit moth), *Grapholita dimorpha* (crab fruit moth), *Leguminivoraglycinivorella* (soybean fruit moth), *Matsumuraeses azukivora* (soybean leafroller), *Adoxophyesorana fasciata* (apple leafroller), and *Adoxophyes* (tea leafroller). The Tortricidae family includes moths such as *Homona magnanima*, *Archips fuscocupreanus*, *Cydiapomonella*, *Tetramoera schistaceana*, *Epinotiaaporema*, *Citripestis sagittiferella*, and *Lobesia botrana*.

[0518] The following species are included: * *Caloptilia theivora* and *Phyllonorycter ringoniella* (Gracillariidae); * *Carposinidae* (Carposina sasakii); *Lyonetiidae* (Lyonetiidae); *Lymantria spp.* (Lymantria dispar) and *Euproctis spp.* (Euproctis pseudoconspersa); *Plutellidae* (Plutella xylostella); *Anarsialineatella* (Anarsialineatella) and *Helcystogramma* (Helcystogramma). Gelechiidae (including *Triannulella*, *Pectinophoragossypiella*, *Phthorimaea operculella*, and *Tutaabsoluta*); Arctiidae (including *Hyphantriacunea*); Castniidae (including *Telchin licus*); Cossidae (including *Cossus insularis*); Geometridae (including *Ascotis selenaria*); Limacodidae (including *Parasalepida*); Stathmopodidae (including *Stathmopoda masinissa*); and Acherontia (including *Acherontia*). Sphingidae (e.g., *Lachesis*); Sesiidae (e.g., *Nokonaferalis*, *Synanthedon hector*, *Synanthedon tenuis*); Hesperiidae (e.g., *Parnara guttata*); Tineidae (e.g., *Tinea translucens*, *Tineola bisselliella*).

[0519] Thysanoptera: Thripidae (Frankliniella occidentalis), palm thistle (Thrips palmi), yellow thrips (Scirtothrips dorsalis), tobacco thrips (Thrips tabaci), flower thrips (Frankliniella intonsa), rice thrips (Stenchaetothrips biformis), American thorny thrips (Echinothrips americanus), avocado thrips (Scirtothrips perseae), etc.; Phlaeothripidae (Haplothrips aculeatus), etc.

[0520] Diptera: Anthomyiidae (including species such as *Delia platura*, *Delia antiqua*, and *Pegomya cunicularia*); Ulidiidae (including species such as *Tetanopsmyopaeformis*); Agromyzidae (including species such as *Agromyza oryzae*, *Liriomyza sativae*, *Liriomyza trifolii*, and *Chromatomyia horticola*); Chloropidae (including species such as *Chloropsoryzae*); Bactrocera cucurbitae (including species such as *Bactrocera dorsalis*, *Bactrocera latifrons*, and *Bactrocera cucurbitae*). Fruit flies include: *Bactroceratryoni*, *Ceratitis capitata*, *Rhagoletis pomonella*, and *Rhacochlaena japonica* (all belonging to the family Tephritidae); rice leaf miners (*Hydrelliagriseola*), *Hydrellia philippina*, and *Hydrellia sasakii* (all belonging to the family Ephydridae); fruit flies including *Drosophila suzukii* and *Drosophila melanogaster* (all belonging to the family Drosophilidae); flea flies including *Megaselia spiracularis* (all belonging to the family Phoridae); midges including *Clogmia albipunctata* (all belonging to the family Psychodidae); and mushroom midges including *Bradysia*. Sciaridae (e.g., *Difformis*); Cecidomyiidae (e.g., *Mayetiola destructor*, *Orseolia oryzae*); Diopsidae (e.g., *Diopsis macrophthalma*).The following species are included: Glossinidae (flies such as *Glossina palpalis* and *Glossina morsitans*); Simuliidae (flying midges such as *Simulium japonicum* and *Simulium damnosum*); Phlebotominae (sandflies); Tipulaaino (gross mosquitoes such as *Tipula aino*, *Tipula oleracea*, and *Tipula paludosa*); and Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culexpipiens pipiens, Culex vishnui, and Aedes albopictus. The Culicidae family includes mosquitoes such as *Aedes aegypti*, *Anopheles sinensis*, *Anopheles gambiae*, *Anopheles stephensi*, *Anopheles coluzzii*, *Anopheles salbimanus*, *Anopheles sundaicus*, *Anopheles arabiensis*, *Anopheles funestus*, *Anopheles darlingi*, *Anopheles farauti*, and *Anopheles minimus*; the Simulidae family includes flies such as *Prosimulium yezoensis* and *Simulium ornatum*; the Tabanidae family includes horseflies such as *Tabanus trigonus*; and the Musca domestica and Muscina species are also mentioned. Muscidae (flies such as *Stabulans*, *Stomoxyscalcitrans*, and *Haematobia irritans*); Calliphoridae (flies); Sarcophagidae (flies);Chironomidae include species such as *Chironomus plumosus*, *Chironomus yoshimatsui*, and *Glyptotendipes tokunagai*; Fannidae are also included.

[0521] Coleoptera: Genus *Diabrotica* spp., including species such as the western corn rootworm (*Diabrotica virgifera virgifera*), the southern corn rootworm (*Diabrotica undecimpunctatahowardi*), the northern corn rootworm (*Diabrotica barberi*), the Mexican corn rootworm (*Diabrotica virgiferazeae*), the spotted cucumber leaf beetle (*Diabrotica balteata*), the Cucurbit Beetle (*Diabrotica speciosa*), the bean leaf beetle (*Cerotoma trifurcata*), the grain leaf beetle (*Oulemamelanopus*), the cucumber beetle (*Aulacophora femoralis*), the striped flea beetle (*Phyllotretastriolata*), the cabbage flea beetle (*Phyllotreta cruciferae*), the western black flea beetle (*Phyllotreta pusilla*), the rapeseed flea beetle (*Psylliodes chrysocephala*), and the hop flea beetle (*Psylliodes*). Chrysomelidae (leaf beetles), including the punctulata, potato beetle (Leptinotarsa ​​decemlineata), rice leaf beetle (Oulema oryzae), grape leaf beetle (Colaspis brunnea), corn flea beetle (Chaetocnema pulicaria), sweet potato flea beetle (Chaetocnema coninis), American potato flea beetle (Epitrix cucumeris), rice iron beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), sweet potato wax beetle (Laccoptera quadrimaculata), and tobacco flea beetle (Epitrix hirtipennis); and Carabidae (earth beetles), including the seedcorn beetle (Stenolophus lecontei) and the corn seed beetle (Clivina impressifrons).The following species belong to the Scarabaeidae family: *Anomala cuprea*, *Anomala rufocuprea*, *Anomala albopilosa*, *Popillia japonica*, *Heptophyllapicea*, *Rhizotrogus majalis*, *Tomarus gibbosus*, *Holotrichia spp.*, *Phyllophaga crinita*, and other species in the *Phyllophaga* genus; *Diloboderus abderus* and other species in the *Diloboderus* genus; *Arenacerus coffeae* and other species in the Anthriibidae family; *Cylasus spp.* (sweet potato weevil). Aponidae family, including *Zabrotes subfasciatus*; Bruchidae family, including *Zabrotes subfasciatus*; Scolytidae family, including *Tomicus piniperda* and *Hypothenemus hampei*; West Indian sweet potato weevil (Euscepespostfasciatus), alfalfa leaf weevil (Hypera postica), maize weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), grain weevil (Sitophilus granarius), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), palm weevil (Rhabdoscelus lineaticollis), cotton boll weevil (Anthonomus grandis), parasitic grain weevil (Sphenophorus venatus), and southern maize long-beaked weevil (Sphenophorus). The family Curculionidae includes species such as callosus, soybean stem weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rust weevil (Scepticus griseus), scepticus uniformis, Aracanthus mourei, and others.Tenebrionidae (including the red flour beetle *Tribolium castaneum*, the mixed flour beetle *Tribolium confusum*, and the black fungus beetle *Alphitobius diaperinus*); Coccinellidae (including the eggplant ladybug *Epilachna vigintioctopunctata*); Bostrychidae (including the brown powder beetle *Lyctus brunneus* and the grain beetle *Rhizopertha dominica*); Ptinidae (spider beetles); Cerambycidae (longhorn beetles including the star longhorn beetle *Anoplophora malasiaca*, *Migdolus fryanus*, and the peach-necked longhorn beetle *Aromiabungii*); Melanotus okinawensis (click beetle), Agriotes fuscicollis (click beetle), and Melanotus (click beetle). Click beetles (Elateridae), including genera such as *Lepidoptera legatus*, *Anchastus* spp., *Conoderus* spp., *Ctenicera* spp., *Limonius* spp., and *Aeolus* spp.; Paederus fuscipes and other rove beetles (Staphylinidae); Dermestidae (Dermestididae), including species such as *Anthrenus verbasci*, *Dermestes maculates*, and *Trogoderma granarium*; Anobiidae (Anobiidae), including species such as *Lasiodermaserricorne* and *Stegobium paniceum*; and Cryptolestes. Species such as *Laemophloeidae* (e.g., *ferrugineus*); *Silvanidae* (e.g., *Oryzaephilus surinamensis*); and *Nitidulidae* (e.g., *Brassicogethesaeneus*).

[0522] Orthoptera: Locusta migratoria, Dociostaurus maroccanus, Chortoicetes terminifera, Nomadacrisseptemfasciata, Locustana pardalina, Anacridium melanorhodon, Calliptamus italicus, Melanoplus differentialis, Melanoplus bivittatus, Melanoplus sanguinipes, Melanoplus femurrubrum, Camnula pellucida, Schistocerca gregaria, Gastrimargus musicus, Austracrisguttulosa, Oxya The family Acrididae includes species such as *Yezoensis*, *Oxya japonica*, and *Patanga succincta*; the family Gryllotalpidae includes species such as *Gryllotalpa orientalis*; the family Gryllidae includes species such as *Acheta domestica* and *Teleogryllus emma*; and the family Tettigoniidae includes species such as *Anabrus simplex*.

[0523] Hymenoptera: Tenthredinidae (leaf bee family), including species such as *Athalia rosae* and *Athalia japonica*; genera such as *Solenopsis* (fire ant genus), *Solenopsis* (tropical fire ant genus), *Atta* (brown leaf-cutting ant genus), *Acromyrmex* (leaf-cutting ant genus), *Paraponera clavata* (bullet ant), *Ochetellus glaber* (hairless stink ant), *Monomoriumpharaonis* (small yellow house ant), *Linepithema humile* (Argentine ant), *Formica japonica* (Japanese black brown ant), *Pristomyrmex punctutus* (striked-breasted leaf-cutting ant), and *Pheidole* (broad-knotted big-headed ant). Formic ants (Camponotus spp.), including *Camponotus noda*, *Pheidolemegacephala*, *Camponotus japonicus*, and *Camponotus obscuripes*; ants (Pogonomyrmex spp.), including *Pogonomyrmex occidentalis*; fire ants (Wasmania spp.), including *Wasmania auropunctata*; yellow ants (Anoplolepis gracilipes); wasps (Vespidae), including *Vespa mandarinia*, *Vespa simillima*, *Vespa analis*, *Vespa velutina*, and domestic wasps (Polistes jokahamae); tree wasps (Urocerus). Families such as *Gigas* (Siricidae) and *Bethylidae* (Byrhynchidae).

[0524] Blattodea: Includes species such as the German cockroach (Blattella germanica) and the family Ectobiidae; species such as the American cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Australian cockroach (Periplaneta australasiae), brown-spotted cockroach (Periplaneta brunnea), and oriental cockroach (Blattaorientalis); species such as the northern subterranean termite (Reticulitermes speratus), the Formosan subterranean termite (Coptotermes formosanus), the small jacaranda termite (Incisitermes minor), the domesticated termite (Cryptotermes domesticus), the black-winged subterranean termite (Odontotermes formosanus), the Neotermite koshunensis, and the Glyptotermes. The termites include species such as *Glyptotermes satsumensis*, *Glyptotermes nakajimai*, *Glyptotermes fuscus*, *Hodotermopsis sjostedti*, *Coptotermes guangzhouensis*, *Reticulitermes amamianus*, *Reticulitermes miyatakei*, *Reticulitermes kanmonensis*, *Nasutitermes takasagoensis*, *Pericapritermes nitobei*, *Sinocapritermes mushae*, and *Cornitermes cumulans*, all belonging to the family Termitidae.

[0525] Siphonaptera: Human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog comb flea (Ctenocephalides canis), rat flea (Xenopsylla cheopis), bird crest flea (Echidnophaga gallinacea)) and other flea families (Pulicidae); skin-penetrating flea (Tunga penetrans) and other sand flea families (Hectopsyllidae); European mouse flea (Nosopsyllus fasciatus) and other hornlea flea families (Ceratophyllidae).

[0526] Order Psocodae: Human head louse (Pediculus humanus capitis) and other louse families (Pediculidae); pubic louse (Pthirus pubis) and other pubic louse families (Pthiridae); blood louse family (Haematopinidae) such as bovine blood louse (Haematopinuseurysternus) and swine blood louse (Haematopinussuis); calf louse (Linognathus vituli), sheep louse (Linognathus ovillus), buffalo blind louse (Solenopotescapillatus) and other gnatidae (Linognathidae); cattle louse (Bovicola bovis), sheep louse (Bovicolaovis), Bovicola breviceps, Damalinia forficula, Werneckiella spp. and other cattle louse families (Bovicoliidae); dog louse (Trichodectes) The following are family names for various lice families: Trichodectidae (including *F. canis* and *Felicola subrostratus*); Menoponidae (including *Menopon gallinae*, *Menacanthus stramineus*, and *Trinoton spp.*); Trimenoponidae (including *Cummingsia spp.*); Trogiidae (including *Trogium pulsatorium*); and Liposcelidae (or Liposcelididae) (including *Liposcelis corrodens*, *Liposcelis bostrychophila*, *Liposcelis pearmani*, and *Liposcelisentomophila*).

[0527] Thysanura: Lepismatidae such as Ctenolepisma villosa and Lepismasaccharina.

[0528] Order Acari: Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligoychus spp., etc., family Tetranychidae; Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus schlechtendali, Aceria The family Eriophyidae includes mites such as *Diospyri*, *Aceria tosichella*, and *Shevtchenkella* sp.; the family Tarsonemidae includes mites such as *Polyphagotarsonemus latus*; the family Tenuipalpidae includes mites such as *Brevipalpus phoenicis*; and the family Tuckerellidae.Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Dermacentor andersoni, Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, Amblyomma americanum, Amblyomma maculatum, Rhipicephalus Microplus, including the ringed tick (Rhipicephalus annulatus), blood-red tick (Rhipicephalus sanguineus), tailed tick (Rhipicephalus appendiculatus), and decolorized tick (Rhipicephalus decoloratus), belonging to the family Ixodidae; Argas persicus, Ornithodoros hermsi, and Ornithodorosturicata, belonging to the family Argasidae; Tyrophagus putrescentiae and Tyrophagus similis, belonging to the family Acaridae; Dermatophagoides farinae and Dermatophagoides pteronyssinus, belonging to the family Pyroglyphidae; and Cheyletus eruditus and Cheyletus malathion, belonging to the family Cheyletus eruditus. Carnivorous mites include the family Cheyletidae, such as *Chelacaropsis moorei* and *Cheyletiella yasguri*.The following are species of mites: sheep itch mite (Psoroptesovis), horse itch mite (Psoroptes equi), mutant knee mite (Knemidocoptesmutans), ear mite (Otodectes cynotis), and skin mite (Chorioptes spp.), belonging to the family Psoroptidae; cat ear mite (Notoedres cati), cat anal mite (Notoedres muris), and human scabies mite (Sarcoptes scabiei), belonging to the family Sarcoptesidae; rabbit tadpole mite (Listrophorus gibbus), belonging to the family Listrophoridae; chicken tussock mite (Dermanyssus gallinae), belonging to the family Dermanyssidae; forest avian tussock mite (Ornithonyssus sylviarum), avian tussock mite (Ornithonyssus bacoti), belonging to the family Macronyssidae; and Varroa mite (Varroa). This includes mites from the families Varoidae (such as *Jacobsoni*), Demodex canis, and Demodex cati (such as *Demodex cati*), as well as mites from the family Trombiculidae (such as *Leptotrombidium akamushi*, *Leptotrombidium pallidum*, and *Leptotrombidium scutellare*).

[0529] Araneae: Eutichuridae (red-clawed spiders such as Cheiracanthium japonicum); Theridiidae (ball spiders such as Latrodectus hasseltii).

[0530] The order Polydesmida includes species such as Oxidus gracilis and Nedyopus tambanus, belonging to the family Paradoxosomatidae.

[0531] Isopoda: Armadillidium vulgare and Armadillidiidae.

[0532] Chilopoda: Scutigeridae (e.g., Thereuonema hilgendorfi); Scolopendridae (e.g., Scolopendra subspinipes); Ethopolyidae (e.g., Bothropolys rugosus).

[0533] Gastropoda: Limacidae (including Limax marginatus and Limaxflavus); Philomycidae (including Meghimatium bilineatum); Ampullariidae (including Pomacea canaliculata); Lymnaeidae (including Austropeplea ollula).

[0534] Nematodes: Rice stem nematode (Aphelenchoides besseyi) and other species in the family Aphelenchoididae; coffee nematode (Pratylenchus coffeae), piercing nematode (Pratylenchus brachyurus), neglected nematode (Pratylenchus neglectus), banana nematode (Radopholus similis) and other species in the family Pratylenchidae; Javan root-knot nematode (Meloidogyne javanica), southern root-knot nematode (Meloidogyne incognita), guava root-knot nematode (Meloidogyne enterolobii), northern root-knot nematode (Meloidogyne hapla), soybean cyst nematode (Heterodera glycines), potato golden nematode (Globodera). The family includes Heteroderidae (such as *Rostochiensis* and *Globodera pallida*); Hoplolaimidae (such as *Rotylenchulus reniformis*); Anguinidae (such as *Nothotylenchus acris* and *Ditylenchus dipsaci*); Tylenchulidae (such as *Tylenchulus semipenetrans*); Longidoridae (such as *Xiphinema index*); Trichodoridae; and Parasitaphelenchidae (such as *Bursaphelenchus xylophilus*).

[0535] Harmful insects, harmful mites and other harmful arthropods, harmful mollusks and harmful nematodes can also refer to harmful insects, harmful mites and other harmful arthropods, harmful mollusks and harmful nematodes whose sensitivity to pesticides, acaricides, molluscicides and nematicides has decreased or who have strong resistance to pesticides.

[0536] As a pest control method of the present invention, it can be implemented by directly applying an effective amount of the compound or composition A of the present invention to the pest, and / or applying it to the habitat of the pest (plants, soil, houses, animals, etc.). Examples of pest control methods of the present invention include foliar treatment, soil treatment, root treatment, spraying treatment, fumigation treatment, water surface treatment, and seed treatment.

[0537] For the compound or composition A of this invention, it is typically mixed with non-active carriers such as solid carriers, liquid carriers, and gaseous carriers, and surfactants, and formulation adjuvants such as binders, dispersants, and stabilizers are added as needed to formulate it into aqueous suspensions, oil suspensions, oils, emulsions, microemulsions, microcapsules, wettable powders, water-dispersible granules, powders, granules, tablets, aerosols, resin formulations, etc. It is not limited to these formulations and can be formulated into the formulations described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517.

[0538] These formulations typically contain 0.0001 to 99% by weight of the compound or composition A of the present invention.

[0539] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomite, zeolite, bentonite, acid clay, palygorskite, silica, ammonium sulfate, vermiculite, perlite, pumice, silica sand, chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.) in powder and granular form, as well as resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0540] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxyl ethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctylamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0541] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[0542] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkyl aryl sulfonates, alkyl sulfates, etc.).

[0543] Examples of adjuvants used in other formulations include binders, dispersants, colorants, and stabilizers. Specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), isopropyl phosphate, and butylated hydroxytoluene.

[0544] In addition, adjuvants may be used as components to enhance or assist the efficacy of the compounds of the present invention. Specifically, examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[0545] In this invention, the plant can be categorized as the whole plant, stem and leaves, flower, spike, fruit, trunk, branch, crown, seed, vegetative reproductive organs, and seedling.

[0546] Vegetative reproductive organs refer to the parts of a plant, such as roots, stems, and leaves, that have the ability to grow when separated from the main body and placed in the 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. It should be noted that stolons are sometimes also called runners, and propagules are also called bulbils, which are divided into broad buds and bulbils. Vine cuttings refer to the shoots (including leaves and stems, without roots) of plants such as sweet potatoes and Japanese yam. Bulbs, corms, tubers, rhizomes, stem cuttings, rootstocks, or tuberous roots are collectively referred to as bulbs. The cultivation of tubers begins by planting tubers in the soil, but the tubers used are usually called seed tubers.

[0547] As a method for controlling pests by applying an effective amount of the compound or composition A of the present invention to the soil, examples include applying an effective amount of the compound or composition A of the present invention to the soil before or after transplanting. More specifically, examples include planting hole treatment (planting hole distribution, planting hole treatment soil mixing), root treatment (root distribution, root soil mixing, root irrigation, late seedling stage root treatment), planting furrow treatment (planting furrow distribution, planting furrow soil mixing), ridge furrow treatment (ridge furrow distribution, ridge furrow soil mixing, growing season ridge furrow distribution), sowing furrow treatment (sowing season ridge furrow distribution, sowing season ridge furrow soil mixing), overall treatment (whole soil distribution, whole soil mixing), ridge planting side treatment, water surface treatment (water surface application, water surface application after water storage), other soil distribution treatments (growing season granule foliar distribution, distribution under the canopy or around the trunk, soil surface distribution, soil surface mixing, sowing hole distribution, ridge surface distribution). Distribute, interplant distribution), other irrigation treatments (soil irrigation, seedling irrigation, pesticide injection, basal irrigation, drip irrigation, chemical solution irrigation), seedling box treatment (seedling box distribution, seedling box irrigation, seedling box pesticide accumulation), seedling tray treatment (seedling tray distribution, seedling tray irrigation, seedling tray pesticide accumulation), seedbed treatment (seedbed distribution, seedbed irrigation, seedling bed distribution, seedling soaking), bed soil mixing treatment (bed soil mixing, pre-sowing bed soil mixing, distribution before sowing and covering with soil, distribution after sowing and covering with soil, soil mixing), and other treatments (cultivated soil mixing, turning in, topsoil mixing, rainwater drip soil mixing, planting location treatment, granular calyx distribution, paste fertilizer mixing).

[0548] As seed treatment, examples include treatment of seeds or vegetative reproductive organs by the compound or composition A of the present invention. More specifically, examples include spraying treatment, where a suspension of the compound or composition A of the present invention is sprayed onto the surface of the seed or vegetative reproductive organ; coating treatment, where the compound or composition A of the present invention is applied to the seed or vegetative reproductive organ; immersion treatment, where the seed is immersed in a solution of the compound or composition A of the present invention for a certain period of time; and methods of coating seeds or vegetative reproductive organs using a carrier containing the compound or composition A of the present invention (coating treatment, granule coating treatment, etc.). Seed potatoes are a particularly good example of the aforementioned vegetative reproductive organ.

[0549] When treating seeds or vegetative reproductive organs with composition A, composition A can be formulated as a single preparation for treating the seeds or vegetative reproductive organs, or composition A can be formulated as multiple different preparations for treating the seeds or vegetative reproductive organs in multiple applications. Examples of methods for treating seeds or vegetative reproductive organs in multiple applications with composition A include: treating with a preparation 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 preparation containing this ingredient; and treating with a preparation containing both the compound of the present invention and this ingredient as active ingredients, air-drying the seeds or vegetative reproductive organs, and then treating with a preparation containing this ingredient other than the ingredient already treated.

[0550] In this invention, a seed or vegetative reproductive organ that retains the compound or composition A of the present invention refers to a seed or vegetative reproductive organ in which the compound or composition A of the present invention is attached to its surface. For the aforementioned seed or vegetative reproductive organ that retains the compound or composition A of the present invention, materials other than the compound or composition A of the present invention may be attached before or after the compound or composition A of the present invention is attached to the seed or vegetative reproductive organ.

[0551] Furthermore, when composition A adheres to the surface of a seed or vegetative reproductive organ by forming a layer, this layer is formed of one or more layers. Additionally, when multiple layers are formed, each layer may contain one or more active ingredients, or it may be formed of a layer containing one or more active ingredients and a layer not containing any active ingredient.

[0552] Seeds or vegetative reproductive organs containing the compound or composition A of the present invention can be obtained, for example, by applying a preparation containing the compound or composition A of the present invention to the seed or vegetative reproductive organ using the aforementioned seed treatment method.

[0553] When the compound or composition A of the present invention is used for pest control in the agricultural field, the application rate is per 10,000 m³. 2 The amount of the compound of the present invention is typically 1 to 10,000 g. When treating seeds or vegetative reproductive organs, the amount of the compound of the present invention applied is typically in the range of 0.001 to 100 g relative to 1 kg of seeds or vegetative reproductive organs. When the compound or composition A of the present invention is formulated as an emulsion, wettable powder, suspension, etc., it is typically diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm and then applied. Granules, powders, etc., are typically applied directly.

[0554] Alternatively, the treatment can be carried out by processing resin preparations into sheets or threads and wrapping them around crops, laying them near crops, or spreading them in the soil around the roots.

[0555] When using the compound or composition A of the present invention to control harmful arthropods inhabiting houses, the dosage, when applied to a surface, is [amount] per 1m². 2 The amount of the compound of the present invention applied to the treatment area is typically 0.01 to 1000 mg, and in the case of treatment in a space, it is applied per 1 m². 3 The amount of the compound of the present invention used in the treatment space is typically 0.01 to 500 mg. When the compound or composition A of the present invention is formulated as an emulsion, wettable powder, suspension, etc., it is usually diluted with water and applied at an active ingredient concentration of 0.1 to 10,000 ppm. Oils, aerosols, fumigants, poison baits, etc., are applied directly.

[0556] When using the compound or composition A of the present invention to control external parasites in livestock such as cattle, horses, pigs, sheep, goats, and chickens, as well as small animals such as dogs, cats, rats, and mice, it can be administered to animals by methods known in veterinary medicine. Specifically, for systemic suppression, it can be administered via methods such as tablets, feed mixing, suppositories, or injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.). For non-systemic suppression, it can be used by methods such as spraying, pouring, or dripping an oily or aqueous solution, washing the animal with a shampoo, or making a collar or ear tag from a resin preparation for the animal to wear. The amount of the compound or composition A of the present invention administered to the animal is generally in the range of 0.1 to 1000 mg relative to 1 kg of the animal's body weight.

[0557] The compound or composition A of the present invention can be used as a control agent for harmful organisms in farmland such as dry fields, paddy fields, lawns, and orchards. Examples of plants that can be cited as examples include the following.

[0558] Maize (dent, flint, soft, popcorn, glutinous, sweet, non-sweet maize), Rice (long-grain, short-grain, medium-grain, Japanese, tropical Japanese, Indian (Indica), Javanese, paddy rice, upland rice, floating rice, direct seeding, transplanting, glutinous rice), Wheat (bread wheat (dull, soft, medium, red, white), durum wheat, spelt wheat, dense-eared wheat, each winter wheat type, spring wheat type), Barley (two-row barley (= brewing barley), six-row barley, naked barley, sticky barley, each...) Winter barley type, spring barley type), rye (winter rye type, spring rye type), black wheat (winter black wheat type, spring black wheat type), oats (winter oat type, spring oat type), sorghum, cotton (land-grown variety, Pima variety), soybean (mature seed harvest variety, edamame variety, green-harvested variety, each with indeterminate, determinate, and semi-determinate growth types), peanut, buckwheat, sugar beet (for sugar production, feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), Canada rapeseed (winter Canada rapeseed type, spring Canada rapeseed type), sunflower (for oil extraction, food). Vegetables used for both medicinal and ornamental purposes include sugarcane, tobacco, tea trees, mulberries, nightshade vegetables (eggplant, tomato, green pepper, chili pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, cantaloupe, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, bok choy, mustard greens, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, chrysanthemum, artichoke, lettuce, etc.), lilyaceous vegetables (scallions, onions, garlic, asparagus, etc.), umbelliferous vegetables (carrots, parsley, celery, parsnips, etc.), chenopodiaceae vegetables (spinach, sauvignon Blanc, etc.), and lamiaceae vegetables (perilla, mint). Basil, strawberries, sweet potatoes, Japanese yam, taro, pears (apples, European pears, Japanese pears, white pears, quince, quince, etc.), stone fruits (peach, plum, nectarine, green plum, cherry, apricot, plum, etc.), citrus fruits (Wenzhou mandarin oranges, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants, turfgrass, and pasture grasses.

[0559] The above-mentioned plants are any commonly cultivated varieties and are not particularly limited. These plants also include plants produced through natural mating, plants produced through mutation, F1 hybrids, and recombinant crops. Examples of recombinant crops include, for instance, plants conferred resistance to herbicides such as isoxaflutole (HPPD inhibitors, imidazoline, ALS inhibitors, EPSP inhibitors, glutamine synthase inhibitors, PPO inhibitors, bromobenzonitrile, or dicamba; plants capable of synthesizing known selective toxins from Bacillus species such as Bacillus thuringiensis; and plants conferred specific insecticidal activity by synthesizing gene fragments identical to endogenous genes from harmful insects and inducing gene silencing (RNAi; RNA interference) in target harmful insects.

[0560] Example

[0561] The following examples, including manufacturing examples, reference manufacturing examples, formulation examples, and test examples, illustrate the present invention in more detail, but the present invention is not limited to these examples.

[0562] In this specification, Me represents methyl, Et represents ethyl, Pr represents propyl, i-Pr represents isopropyl, Bu represents butyl, i-Bu represents isobutyl, t-Bu represents tert-butyl, Pen represents pentyl, c-Pr represents cyclopropyl, c-Bu represents cyclobutyl, c-Pen represents cyclopentyl, c-Hex represents cyclohexyl, and Ph represents phenyl.

[0563] First, examples of manufacturing the compounds of the present invention are shown.

[0564] When determining the physical properties of a compound using 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) are recorded. The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.

[0565] [LC conditions]

[0566] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Generally Incorporated Chemical Substances Evaluation and Research Organization).

[0567] UV measurement wavelength: 254nm

[0568] Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile

[0569] Flow rate: 2.0 mL / min

[0570] Pumps: 2 units of LC-20AD (manufactured by Shimadzu Corporation) (high pressure gradient)

[0571] Gradient conditions: The solution is delivered using the concentration gradient described in [Table LC1].

[0572] [Table 1]

[0573] [Table LC1]

[0574] Time (minutes) Liquid A (%) Liquid B (%) 0.019010 2.000100 4.000100 4.019010 surface

[0575] [MS conditions]

[0576] Detector: LCMS-2020 (manufactured by Shimadzu Corporation)

[0577] Ionization method: DUIS

[0578] Refer to manufacturing example 1-1

[0579] Under a nitrogen atmosphere, a mixture of 1.06 g of 1,5-dibromo-2,4-dimethylbenzene, 1.03 g of methyl acetoacetate, 0.09 g of palladium(II) acetate, 0.17 g of 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, 2.55 g of tripotassium phosphate, and 20 mL of toluene was stirred under reflux for 2 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.71 g of intermediate 1-1 represented by the following formula.

[0580] [Chemical Formula 28]

[0581]

[0582] Intermediate 1-1: 1 H-NMR(CDCl3)δ:12.95(1H,s),7.23(1H,s),7.10(1H,s),3.68(3H,s),2.37(3H,s),2.07(3H,s),1.77(3H,s).

[0583] Refer to manufacturing examples 1-2

[0584] Add 0.3 mL of 28% sodium methoxide methanol solution to a mixture of 0.30 g of intermediate 1-1, 2 mL of THF, and 2 mL of methanol, and stir at 60 °C for 3 hours. Add a saturated aqueous solution of ammonium chloride to the resulting mixture and extract with ethyl acetate. Wash the resulting organic layer with saturated brine, dry with anhydrous sodium sulfate, and concentrate under reduced pressure to obtain 0.22 g of intermediate 1-2 represented by the following formula.

[0585] [Chemical Formula 29]

[0586]

[0587] Intermediate 1-2: 1 H-NMR(CDCl3)δ:7.35(1H,s),7.05(1H,s),3.69(3H,s),3.57(2H,s),2.33(3H,s),2.22(3H,s).

[0588] Refer to manufacturing examples 1-3

[0589] A mixture of 3.72 g of intermediate 1-2, 3.45 g of N,N-dimethylformamide dimethyl acetal, and 15 mL of DMF was stirred under reflux for one and a half days. Water was added to the resulting mixture, and extraction was performed using MTBE. The resulting organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3.10 g of intermediate 1-3 represented by the following formula.

[0590] [Chemical Formula 30]

[0591]

[0592] Intermediates 1-3: 1 H-NMR(CDCl3)δ:7.56(1H,s),7.28(1H,s),7.03(1H,s),3.61(3H,s),2.67(6H,s),2.35(3H,s),2.10(3H,s).

[0593] Refer to manufacturing examples 1-4

[0594] Under ice cooling, 5 mL of 2N hydrochloric acid was added to a mixture of 0.27 g of intermediates 1-3 and 10 mL of methanol, and the mixture was stirred at room temperature for 3 hours. Saturated brine was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.23 g of intermediates 1-4 represented by the following formula.

[0595] [Chemical Formula 31]

[0596]

[0597] Refer to manufacturing examples 1-5

[0598] To a mixture of 0.23 g of intermediates 1-4, 0.34 g of cesium carbonate, and 4 mL of NMP, 0.15 g of dimethyl sulfuric acid was added, and the mixture was stirred at room temperature for 3 hours. Saturated brine was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.19 g of intermediates 1-5 represented by the following formula.

[0599] [Chemical Formula 32]

[0600]

[0601] Intermediates 1-5: 1 H-NMR(CDCl3)δ:7.55(1H,s),7.27(1H,s),7.10(1H,s),3.84(3H,s),3.70(3H,s),2.35(3H,s),2.09(3H,s).

[0602] Reference Manufacturing Example 2

[0603] Under a nitrogen atmosphere, a mixture of 1.0 g of intermediate 1-5, 1.1 g of bis(pinacol)diboron, 0.24 g of PdCl2(dppf), 0.66 g of tripotassium phosphate, and 30 mL of dimethoxyethane was stirred at 80 °C for 6 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.0 g of intermediate 2-1 represented by the following formula.

[0604] [Chemical Formula 33]

[0605]

[0606] Intermediate 2-1: 1 H-NMR(CDCl3)δ:7.54(1H,s),7.50(1H,s),7.04(1H,s),3.80(3H,s),3.68(3H,s),2.50(3H,s),2.14(3H,s),1.31(12H,s).

[0607] Reference Manufacturing Example 3

[0608] Under a nitrogen atmosphere, a mixture of 2.0 g of intermediate 1-5, 0.47 g of bis(triphenylphosphine)palladium(II) dichloride, 4.4 mL of tributyl(1-ethoxyvinyl)tin, and 20 mL of 1,4-dioxane was stirred at 110 °C for 4 hours. 1 N hydrochloric acid was added to the resulting mixture, and the mixture was stirred at room temperature for 1 hour. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.4 g of intermediate 3-1 represented by the following formula.

[0609] [Chemical Formula 34]

[0610]

[0611] Intermediate 3-1: 1 H-NMR(CDCl3)δ:7.60(1H,s),7.50(1H,s),7.11(1H,s),3.85(3H,s),3.72(3H,s),2.55(3H,s),2.52(3H,s),2.18(3H,s).

[0612] Refer to manufacturing example 4

[0613] A mixture of 0.54 g of intermediate 2-1, 0.50 g of m-chloroperoxybenzoic acid, 5 mL of acetonitrile, 5 mL of ethanol, and 5 mL of water was stirred for 2.5 hours at room temperature. An aqueous solution of sodium thiosulfate and an aqueous solution of sodium bicarbonate were added to the resulting mixture, and the mixture was stirred at room temperature for 2 hours. The resulting mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.37 g of intermediate 4-1 represented by the following formula.

[0614] [Chemical Formula 35]

[0615]

[0616] Intermediate 4-1: 1 H-NMR(CDCl3)δ:7.54(1H,s),6.98(1H,s),6.55(1H,s),4.51(1H,s),3.83(3H,s),3.70(3H,s),2.21(3H,s),2.07(3H,s).

[0617] Reference Manufacturing Example 5

[0618] Under a nitrogen atmosphere, a mixture of 2.0 g of 3-bromo-4,5-dimethylphenol, 3.8 g of bis(pinacol)diboron, 0.36 g of PdCl2(dppf), 2.0 g of potassium acetate, and 25 mL of DMSO was stirred at 80 °C for 7 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.6 g of intermediate 5-1 represented by the following formula.

[0619] [Chemical Formula 36]

[0620]

[0621] Intermediate 5-1: 1 H-NMR (CDCl3) δ: 7.05 (1H, d), 6.75 (1H, d), 4.62 (1H, br s), 2.38 (3H, s), 2.22 (3H, s), 1.34 (12H, s).

[0622] Refer to manufacturing example 5-1

[0623] The following shows the compounds manufactured according to Reference Manufacturing Example 5 and their physical properties.

[0624] In the compound represented by formula (C5-a), R 1 R 2a R 2b and R X The compounds are any combination of those listed in [Table A1].

[0625] [Chemical Formula 37]

[0626]

[0627] [Table 2]

[0628] [Table A1]

[0629] intermediate R 1 R 2a R 2b R X 5-2MeFHOH5-3MeOMeHOH surface

[0630] Intermediate 5-2: 1 H-NMR (CDCl3) δ: 7.38 (1H, d), 6.87 (1H, d), 4.83 (1H, d), 2.45 (3H, s), 1.33 (12H, s).

[0631] Intermediate 5-3: 1 H-NMR (CDCl3) δ: 7.31 (1H, s), 6.66 (1H, s), 5.29 (1H, s), 3.88 (3H, s), 2.48 (3H, s), 1.32 (12H, s).

[0632] Reference Manufacturing Example 6

[0633] Under a nitrogen atmosphere, a mixture of 2.5 g of intermediate 5-1, 2.9 g of (Z)-2-iodo-3-methoxyacrylate, 0.21 g of 2-(dicyclohexylphosphino)-2',6'-dimethoxybiphenyl, 0.23 g of Pd2(dba)3, 4.22 g of tripotassium phosphate, 25 mL of toluene, and 5 mL of water was stirred at 110 °C for 4 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.6 g of intermediate 6-1 represented by the following formula.

[0634] [Chemical Formula 38]

[0635]

[0636] Intermediate 6-1: 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 6.64 (1H, d), 6.46 (1H, d), 4.82-4.78 (1H, br m), 3.82 (3H, s), 3.70 (3H, s), 2.24 (3H, s), 1.99 (3H, s).

[0637] Refer to manufacturing example 6-1

[0638] The following shows the compounds manufactured according to Reference Manufacturing Example 6 and their physical properties.

[0639] In the compound represented by formula (C6-a), R 1 R 2a R 2b E a X and L are compounds in any combination listed in [Table A2].

[0640] [Chemical Formula 39]

[0641]

[0642] [Table 3]

[0643] [Table A2]

[0644] intermediate R 1 R 2a R 2b E a XL6-2MeFHOHCHO6-3MeOMeHOHCHO surface

[0645] Intermediate 6-2: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 6.93 (1H, d), 6.76 (1H, d), 4.96 (1H, d), 3.84 (3H, s), 3.71 (3H, s), 2.08 (3H, s).

[0646] Intermediate 6-3: 1H-NMR (CDCl3) δ: 7.54 (1H, s), 6.72 (1H, s), 6.70 (1H, s), 5.40 (1H, s), 3.87 (3H, s), 3.83 (3H, s), 3.70 (3H, s), 2.11 (3H, s).

[0647] Reference Manufacturing Example 7

[0648] Under a nitrogen atmosphere, at 0°C, 0.46 mL of triethylamine and 0.50 mL of trifluoroacetic anhydride were added sequentially to a mixture of 0.6 g of intermediate 6-1 and 6 mL of chloroform, and the mixture was stirred for 30 minutes. An aqueous solution of sodium bicarbonate was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 0.70 g of intermediate 7-1 represented by the following formula.

[0649] [Chemical Formula 40]

[0650]

[0651] Intermediate 7-1: 1 H-NMR(CDCl3)δ:7.58(1H,s),7.02(1H,d),6.89(1H,d),3.85(3H,s),3.71(3H,s),2.32(3H,s),2.07(3H,s).

[0652] Refer to manufacturing example 7-1

[0653] The following shows the compounds manufactured according to Reference Manufacturing Example 7 and their physical properties.

[0654] In the compound represented by formula (C7-a), R 1 R 2a R 2b X and L are compounds in any combination listed in [Table A3].

[0655] [Chemical Formula 41]

[0656]

[0657] [Table 4]

[0658] [Table A3]

[0659] intermediate R 1 R 2a R 2b XL7-2MeFHCHO7-3MeOMeHCHO surface

[0660] Intermediate 7-2: 1 H-NMR (CDCl3) δ: 7.59 (1H, s), 7.12-7.05 (2H, m), 3.86 (3H, s), 3.71 (3H, s), 2.18 (3H, s).

[0661] Intermediate 7-3: 1 H-NMR (CDCl3) δ: 7.57 (1H, s), 6.97 (1H, s), 6.87 (1H, s), 3.90 (3H, s), 3.85 (3H, s), 3.71 (3H, s), 2.19 (3H, s).

[0662] Reference Manufacturing Example 8

[0663] Under a nitrogen atmosphere, 12 mL of butyllithium (1.6 M hexane solution) was added dropwise to a mixture of 5 g of 1,5-dibromo-2,4-dimethylbenzene and 30 mL of THF at -78 °C, and the mixture was stirred at -78 °C for 1 hour. 2.5 g of dimethyl oxalate was added to the resulting mixture, and the mixture was stirred at 0 °C for 3 hours. A saturated aqueous solution of ammonium chloride was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 3.9 g of intermediate 8-1 represented by the following formula.

[0664] [Chemical Formula 42]

[0665]

[0666] Intermediate 8-1: 1 H-NMR (CDCl3) δ: 7.83 (1H, s), 7.18 (1H, s), 3.97 (3H, s), 2.51 (3H, s), 2.42 (3H, s).

[0667] Refer to manufacturing example 8-1

[0668] The following shows the compounds manufactured according to Reference Manufacturing Example 8 and their physical properties.

[0669] [Chemical Formula 43]

[0670]

[0671] Intermediate 8-2: 1 H-NMR(CDCl3)δ:7.79-7.72(1H,m),6.96(1H,m),3.97(3H,s).

[0672] Reference Manufacturing Example 9

[0673] A mixture of 3.5 g of intermediate 8-1, 2.3 g of O-methylhydroxylamine hydrochloride, and 80 mL of ethanol was stirred at 55 °C for 6 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.3 g of intermediate 9-1 represented by the following formula.

[0674] [Chemical Formula 44]

[0675]

[0676] Intermediate 9-1: 1 H-NMR(CDCl3)δ:7.26(1H,s),7.13(1H,s),4.06(3H,s),3.88(3H,s),2.37(3H,s),2.10(3H,s).

[0677] Refer to manufacturing example 9-1

[0678] The following shows the compounds manufactured according to Reference Manufacturing Example 9 and their physical properties.

[0679] [Chemical Formula 45]

[0680]

[0681] Intermediate 9-2: 1 H-NMR(CDCl3)δ:7.64-7.57(1H,m),6.92-6.86(1H,m),4.14(3H,s),3.91(3H,s).

[0682] Manufacturing Example 1

[0683] At room temperature, 0.20 g of intermediate 3-1, 0.13 g of O-methylhydroxylamine hydrochloride, and 5 mL of ethanol were mixed with 0.10 mL of pyridine, and the mixture was stirred overnight at room temperature. The resulting mixture was diluted with ethyl acetate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 3:7) to give 0.22 g of compound 1-1 of the present invention represented by the following formula.

[0684] [Chemical Formula 46]

[0685]

[0686] Compound 1-1 of the present invention: 1 H-NMR(CDCl3)δ:7.55(1H,s),7.06(1H,s),6.98(1H,s),3.95(3H,s),3.81(3H,s),3.68(3H,s),2.33(3H,s),2.15(3H,s),2.14(3H,s).

[0687] Manufacturing Example 1-1

[0688] The following shows the compounds manufactured according to Manufacturing Example 1 and their physical properties.

[0689] In the compound represented by formula (1-1), R 1 R 2a R 2b R 3 R 4 X, L and X are compounds in any combination listed in [Table A4].

[0690] [Chemical Formula 47]

[0691]

[0692] [Table 5]

[0693] [Table A4]

[0694]

[0695] Compounds 1-2 of this invention: 1 H-NMR(CDCl3)δ:7.55(1H,s),7.06(1H,s),6.98(1H,s),4.19(2H,q),3.80 (3H,s),3.68(3H,s),2.34(3H,s),2.16(3H,s),2.14(3H,s),1.31(3H,t).

[0696] Compounds 1-3 of this invention: 1 H-NMR(CDCl3)δ:7.55(1H,s),7.06(1H,s),6.99(1H,s),3.96(2H,d),3.81(3H,s),3.68(3H,s), 2.35(3H,s),2.19(3H,s),2.14(3H,s),1.25-1.15(1H,m),0.58-0.52(2H,m),0.33-0.28(2H,m).

[0697] Compounds 1-4 of this invention: 1 H-NMR(CDCl3)δ:7.58(1H,s),7.33-7.27(2H,m),7.25-7.21(2H,m),7.13(1H,s),7.09(1H ,s),7.02-6.98(1H,m),3.83(3H,s),3.71(3H,s),2.43(3H,s),2.39(3H,s),2.18(3H,s).

[0698] Compounds 1-5 of this invention: 1 H-NMR(CDCl3)δ:7.55(1H,s),7.43-7.32(5H,m),7.04(1H,s),6.97(1H,s),5 .19(2H,s),3.80(3H,s),3.68(3H,s),2.25(3H,s),2.20(3H,s),2.13(3H,s).

[0699] Compounds 1-6 of this invention: 1 H-NMR(CDCl3)δ:7.56(1H,s),7.07(1H,s),6.98(1H,s),4.74(1H,t),4.62(1H,t),4.41 (1H,t),4.34(1H,t),3.82(3H,s),3.69(3H,s),2.34(3H,s),2.20(3H,s),2.14(3H,s).

[0700] Compounds 1-7 of this invention: 1 H-NMR(CDCl3)δ:8.29(1H,s),7.56(1H,s),7.44(1H,s),7.05(1H,s),4.21 (2H,q),3.82(3H,s),3.69(3H,s),2.38(3H,s),2.15(3H,s),1.32(3H,t).

[0701] Compounds 1-8 of this invention: 1H-NMR(CDCl3)δ:8.35(1H,s),7.56(1H,s),7.43-7.40(2H,m),7.38-7.30(4H,m) ,7.05(1H,s),5.19(2H,s),3.82(3H,s),3.69(3H,s),2.36(3H,s),2.15(3H,s).

[0702] Compounds 1-9 of this invention: 1 H-NMR(CDCl3)δ:8.33(1H,s),7.56(1H,s),7.40(1H,s),7.37-7.30(4H,m),7 .05(1H,s),5.14(2H,s),3.82(3H,s),3.69(3H,s),2.36(3H,s),2.15(3H,s).

[0703] Manufacturing Example 2

[0704] Under a nitrogen atmosphere, a mixture of 0.10 g of intermediate 1-5, 0.02 g of PdCl2(PPh3)2, 0.15 mL of cyclopropylacetylene, 1.0 mL of tetrabutylammonium fluoride (1 mol / L THF solution), and 3 mL of THF was stirred at 80 °C for 6 hours. An aqueous sodium bicarbonate solution was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:3) to give 0.09 g of compound 2-1 of the present invention, represented by the following formula.

[0705] [Chemical Formula 48]

[0706]

[0707] Compound 2-1 of this invention: 1 H-NMR(CDCl3)δ:7.53(1H,s),7.10(1H,s),7.02(1H,s),3.81(3H,s),3.68(3H,s), 2.34(3H,s),2.11(3H,s),1.49-1.42(1H,m),0.88-0.82(2H,m),0.79-0.74(2H,m).

[0708] Manufacturing Example 2-1

[0709] The following shows the compounds manufactured according to Manufacturing Example 2 and their physical properties.

[0710] In the compound represented by formula (2-1), R 1 R 2a R2b R 5 X, L and X are compounds in any combination listed in [Table B1].

[0711] [Chemical Formula 49]

[0712]

[0713] [Table 6]

[0714] [Table B1]

[0715] Compound R of the present invention 1 R 2a R 2b R 5 XL2-2MeMeHt-BuNO2-3MeMeHt-BuCHO2-4FFHPhNO surface

[0716] Compound 2-2 of this invention: 1 H-NMR (CDCl3) δ: 7.09 (1H, s), 7.06 (1H, s), 4.04 (3H, s), 3.86 (3H, s), 2.37 (3H, s), 2.12 (3H, s), 1.31 (9H, s).

[0717] Compounds 2-3 of this invention: LCMS: 301[M+H] + RT = 2.33 minutes. Compounds 2-4 of this invention: 1 H-NMR (CDCl3) δ: 7.62-7.51 (3H, m), 7.38-7.34 (3H, m), 6.98-6.92 (1H, m), 4.14 (3H, s), 3.91 (3H, s).

[0718] Manufacturing Example 3

[0719] A mixture of 0.18 g of intermediate 4-1, 0.06 mL of butanol, 0.13 g of bis(2-methoxyethyl) azodicarbonate, 0.13 g of triphenylphosphine, and 4 mL of chloroform was stirred for 4 hours at room temperature. An aqueous solution of sodium bicarbonate was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:3) to give 0.13 g of compound 3-1 of the present invention, represented by the following formula.

[0720] [Chemical Formula 50]

[0721]

[0722] Compound 3-1 of this invention: 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 6.98 (1H, s), 6.56 (1H, s), 3.92 (2H, t), 3.82 (3H, s), 3.7 0(3H,s), 2.18(3H,s), 2.07(3H,s), 1.79-1.70(2H,m), 1.54-1.44(2H,m), 0.96(3H,t).

[0723] Manufacturing Example 3-1

[0724] The following shows the compound manufactured according to manufacturing example 3 and its physical properties.

[0725] In the compound represented by formula (3-1), R 1 R 2a R 2b R 6 X, L and X are compounds in any combination listed in [Table A5].

[0726] [Chemical Formula 51]

[0727]

[0728] [Table 7]

[0729] [Table A5]

[0730] Compound R of the present invention 1 R 2a R 2b R 6 XL3-2MeHMeBuCHO3-3MeFHBuCHO3-4MeOMeHBuCHO surface

[0731] Compound 3-2 of this invention: 1 H-NMR (CDCl3) δ: 7.54 (1H, s), 6.70 (1H, d), 6.52 (1H, d), 3.91 (2H, t), 3.82 (3H, s), 3.7 0(3H,s), 2.26(3H,s), 2.00(3H,s), 1.77-1.69(2H,m), 1.52-1.41(2H,m), 0.96(3H,t).

[0732] Compound 3-3 of this invention: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 6.93 (1H, d), 6.70 (1H, d), 3.99 (2H, t), 3.84 (3H, s ), 3.71 (3H, s), 2.08 (3H, s), 1.82-1.73 (2H, m), 1.53-1.43 (2H, m), 0.96 (3H, t).

[0733] Compounds 3-4 of this invention: 1 H-NMR (CDCl3) δ: 7.55 (1H, s), 6.73 (1H, s), 6.63 (1H, s), 3.97 (2H, t), 3.85 (3H, s), 3.8 4(3H,s), 3.71(3H,s), 2.12(3H,s), 1.84-1.74(2H,m), 1.52-1.41(2H,m), 0.95(3H,t).

[0734] Manufacturing Example 4

[0735] Under a nitrogen atmosphere, a mixture of 0.20 g of intermediate 7-2, 0.11 g of 3-methoxyphenylboronic acid, 0.02 g of PdCl2(dppf), 0.23 g of tripotassium phosphate, 4 mL of dimethoxyethane, and 0.4 mL of water was stirred at 80 °C for 3 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:3) to give 0.16 g of compound 4-1 of the present invention, represented by the following formula.

[0736] [Chemical Formula 52]

[0737]

[0738] Compound 4-1 of this invention: 1 H-NMR(CDCl3)δ:7.59(1H,s),7.33(1H,t),7.19(1H,d),7.16-7.09(2H,m),7.02 (1H,d),6.91-6.87(1H,m),3.84(3H,s),3.84(3H,s),3.72(3H,s),2.20(3H,s).

[0739] Manufacturing Example 4-1

[0740] The following shows the compounds manufactured according to Manufacturing Example 4 and their physical properties.

[0741] In the compound represented by formula (4-1), R 1 R2a R 2b R 3a R 4a R 5a R 6a R 7a X and L are compounds in any combination listed in [Table A6].

[0742] [Chemical Formula 53]

[0743]

[0744] [Table 8]

[0745] [Table A6]

[0746]

[0747] Compound 4-2 of this invention: 1 H-NMR(CDCl3)δ:7.57(1H,s),7.40-7.30(5H,m),7.15(1H,s),7.01(1H,s),3.83(3H,s),3.71(3H,s),2.26(3H,s),2.20(3H,s).

[0748] Compound 4-3 of this invention: 1 H-NMR(CDCl3)δ:7.57(1H,s),7.30(1H,t),7.14(1H,s),7.01(1H,s),6.95-6.92(1H,m ),6.90-6.84(2H,m),3.83(3H,s),3.82(3H,s),3.71(3H,s),2.26(3H,s),2.20(3H,s).

[0749] Compound 4-4 of this invention: 1 H-NMR(CDCl3)δ:7.58(1H,s),7.28-7.20(4H,m),7.10(1H,s),6.97(1H,s),3.82(3H,s),3.71(3H,s),2.34(3H,s),2.31(3H,s),2.13(3H,s).

[0750] Compounds 4-5 of this invention: 1H-NMR(CDCl3)δ:7.60(1H,s),7.35(1H,d),7.32(1H,t),7.20(1H,d),7.19-7.15(1H,m),7.11 (1H,t),6.87-6.83(1H,m),3.85(3H,s),3.83(3H,s),3.71(3H,s),2.36(3H,s),2.12(3H,s).

[0751] Compounds 4-6 of this invention: 1 H-NMR(CDCl3)δ:7.83(1H,s),7.81-7.77(1H,m),7.64-7.59(2H,m),7.52 (1H,t),7.16(1H,d),7.06(1H,d),3.86(3H,s),3.73(3H,s),2.22(3H,s).

[0752] Compounds 4-7 of this invention: 1 H-NMR(CDCl3)δ:7.42-7.31(5H,m),7.17(1H,s),7.00(1H,s),4.07(3H,s),3.88(3H,s),2.27(3H,s),2.20(3H,s).

[0753] Compounds 4-8 of this invention: 1 H-NMR(CDCl3)δ:7.35-7.29(3H,m),7.23-7.19(1H,m),7.17(1H,s),6.96(1H,s),4.07(3H,s),3.88(3H,s),2.26(3H,s),2.20(3H,s).

[0754] Compounds 4-9 of this invention: 1 H-NMR(CDCl3)δ:7.34-7.28(1H,m),7.17(1H,s),7.00(1H,s),6.93-6.86 (3H,m),4.07(3H,s),3.87(3H,s),3.82(3H,s),2.28(3H,s),2.20(3H,s).

[0755] Compounds 4-10 of this invention: 1 H-NMR(CDCl3)δ:7.45-7.39(1H,m),7.28-7.25(1H,m),7.21-7.17(3H,m),6.98(1H,s),4.07(3H,s),3.88(3H,s),2.27(3H,s),2.21(3H,s).

[0756] Compound 4-11 of this invention: 1 H-NMR(CDCl3)δ:7.61-7.57(2H,m),7.53-7.50(2H,m),7.21-7.19(1H,m),6.98(1H,s),4.07(3H,s),3.88(3H,s),2.26(3H,s),2.21(3H,s).

[0757] Compounds 4-12 of this invention: 1 H-NMR(CDCl3)δ:7.41-7.28(5H,m),7.16(1H,s),6.99(1H,s),6.78(1H,s),3.97(3H,s),2.93(3H,d),2.26(3H,s),2.20(3H,s).

[0758] Compounds 4-13 of this invention: 1 H-NMR(CDCl3)δ:7.34-7.32(1H,m),7.31-7.27(2H,m),7.23-7.20(1H,m),7.15(1H,s),6.95(1H,s),6.79(1H,br s),3.98(3H,s),2.93(3H,d),2.25(3H,s),2.19(3H,s).

[0759] Compound 4-14 of this invention: LCMS: 311[M+H] + RT = 2.19 minutes

[0760] Compounds 4-15 of this invention: 1 H-NMR(CDCl3)δ:7.57(1H,s),7.31-7.25(1H,m),7.17-7.10(4H,m),7.00 (1H,s),3.82(3H,s),3.71(3H,s),2.38(3H,s),2.26(3H,s),2.19(3H,s).

[0761] Compound 4-16 of this invention: LCMS: 311[M+H] + RT = 2.20 minutes

[0762] Compound 4-17 of this invention: LCMS: 315 [M+H] + RT = 2.09 minutes

[0763] Compounds 4-18 of this invention: 1H-NMR(CDCl3)δ:7.58(1H,s),7.37-7.31(1H,m),7.16-7.10(2H,m),7.08-6.97(3H,m),3.84(3H,s),3.71(3H,s),2.25(3H,s),2.20(3H,s).

[0764] Compound 4-19 of this invention: LCMS: 315 [M+H] + RT = 2.12 minutes

[0765] Compound 4-20 of this invention: LCMS: 327 [M+H] + RT = 2.07 minutes

[0766] Compound 4-21 of this invention: LCMS: 327[M+H] + RT = 2.08 minutes

[0767] Compound 4-22 of this invention: LCMS: 331[M+H] + RT = 2.22 minutes

[0768] Compound 4-23 of this invention: LCMS: 343 [M+H] + RT = 2.18 minutes

[0769] Compound 4-24 of this invention: 1 H-NMR(CDCl3)δ:7.56(1H,s),7.37-7.31(3H,m),7.13-7.03(5H,m),7.00-6.94(3H,m),3.82(3H,s),3.70(3H,s),2.24(3H,s),2.18(3H,s).

[0770] Compound 4-25 of this invention: 1 H-NMR(CDCl3)δ:7.57(1H,s),7.47-7.27(6H,m),7.13(1H,s),7.00(1H,s),6.97 -6.92(3H,m),5.08(2H,s),3.82(3H,s),3.71(3H,s),2.21(3H,s),2.19(3H,s).

[0771] Compound 4-26 of this invention: LCMS: 342[M+H] + RT = 2.11 minutes

[0772] Compound 4-27 of this invention: LCMS: 337[M+H] + RT = 2.31 minutes

[0773] Compound 4-28 of this invention: LCMS: 345 [M+H] + RT = 2.04 minutes

[0774] Compound 4-29 of this invention: LCMS: 333 [M+H] + RT = 2.16 minutes

[0775] Compound 4-30 of this invention: LCMS: 324 [M+H] + RT = 2.04 minutes

[0776] Manufacturing Example 5

[0777] Under a nitrogen atmosphere, a mixture of 0.18 g of intermediate 2-1, 0.09 mL of 2-bromo-3-fluoropyridine, 0.02 g of PdCl2(dppf), 0.24 g of tripotassium phosphate, 4 mL of dimethoxyethane, and 1 mL of water was stirred at 80 °C for 8 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 2:3) to give 0.10 g of compound 5-1 of the present invention, represented by the following formula.

[0778] [Chemical Formula 54]

[0779]

[0780] Compound 5-1 of this invention: 1 H-NMR(CDCl3)δ:8.51-8.49(1H,m),7.57(1H,s),7.49-7.43(1H,m),7.31-7.25(1H ,m),7.17(1H,d),7.14(1H,s),3.81(3H,s),3.68(3H,s),2.24(3H,s),2.20(3H,s).

[0781] Manufacturing Example 5-1

[0782] The following shows the compounds manufactured according to Manufacturing Example 5 and their physical properties.

[0783] In the compound represented by formula (5-1), R 1 R 2a R 2b E b X and L are compounds in any combination listed in [Table B2]. (● indicates the bonding site with the benzene ring.)

[0784] [Chemical Formula 55]

[0785]

[0786] [Table 9]

[0787] [Table B2]

[0788]

[0789] Compound 5-2 of this invention: 1 H-NMR(CDCl3)δ:7.89(1H,t),7.63-7.57(3H,m),7.19(1H,s),7.17(1H,s),3.83(3H,s),3.70(3H,s),2.40(3H,s),2.20(3H,s).

[0790] Compound 5-3 of this invention: 1 H-NMR(CDCl3)δ:7.18(1H,s),7.13(1H,d),7.01(1H,s),6.90(1H,d),4.07(3H,s),3.87(3H,s),2.22(3H,s),2.20(3H,s).

[0791] Compounds 5-4 of this invention: 1 H-NMR(CDCl3)δ:7.18(1H,s),7.13(1H,d),7.01(1H,s),6.90(1H,d),4.07(3H,s),3.87(3H,s),2.22(3H,s),2.20(3H,s).

[0792] Compound 5-5 of this invention: 1 H-NMR(CDCl3)δ:7.87(1H,s),7.84(1H,s),7.58(1H,s),7.16(1H,s),7.07(1H,s),3.84(3H,s),3.72(3H,s),2.35(3H,s),2.18(3H,s).

[0793] Manufacturing Example 6

[0794] Under a nitrogen atmosphere, a mixture of 0.10 g of intermediate 1-5, 0.08 g of 1-cyclopentenylboronic acid, 0.02 g of PdCl2(dppf), 0.21 g of tripotassium phosphate, 4 mL of dimethoxyethane, and 1 mL of water was stirred at 80 °C for 6 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 1:3) to give 0.08 g of compound 6-1 of the present invention, represented by the following formula.

[0795] [Chemical Formula 56]

[0796]

[0797] Compound 6-1 of this invention: 1 H-NMR(CDCl3)δ:7.55(1H,s),7.02(1H,s),6.82(1H,s),5.58-5.54(1H,m),3.81(3H,s),3.70(3 H,s),2.24(3H,s),2.21-2.16(2H,m),2.16-2.11(5H,m),1.76-1.69(2H,m),1.69-1.62(2H,m).

[0798] Manufacturing Example 6-1

[0799] The following shows the compounds manufactured according to Manufacturing Example 6 and their physical properties.

[0800] [Chemical Formula 57]

[0801]

[0802] Compound 6-2 of this invention: LCMS: 287[M+H] + RT = 2.25 minutes

[0803] Next, examples of compounds and intermediates of the present invention manufactured in accordance with any of the manufacturing examples described in the embodiments and the manufacturing methods described in this specification will be shown below.

[0804] In the compound represented by formula (1A) (hereinafter referred to as compound (1A)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X2 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX1).

[0805] [Chemical Formula 58]

[0806]

[0807] Combination A consists of substituent numbers ZA1 to ZA364. Substituent numbers ZA1 to ZA364 refer to R in compound (1A). 3 and R 4 The combination of [substituent number; R] is denoted below as [substituent number; R]. 3 ,R 4 For example, the substituent number ZA2 refers to R. 3 It is ethyl and R 4 It is a combination of hydrogen atoms.

[0808] Combination A

[0809] [ZA1;Me,H],[ZA2;Et,H],[ZA3;Pr,H],[ZA4;Bu,H],[ZA5;Pen,H],[ZA6;Hex,H],[ZA7;i-Pr,H],[ZA8;i-Bu,H],[ZA9;t-Bu,H],[ZA10;c-Pr,H],[ZA11;c-Bu,H],[ZA12;c-Pen,H],[ZA13;c-Hex,H],[ZA14;CH2c-Pr,H],[ZA15;CH2c-Pen,H],[ZA16;CH2c-Hex,H],[ZA17;CH2CH=CH2,H],[ZA18;CH2CH=CHMe,H],[ZA19;CH2CH=CMe2,H],[ZA20;CH2C≡CH,H],[ZA21;CH2C≡CMe,H],[ZA22;CH2Ph,H],[ZA23;CH2(2-F-Ph),H],[ZA24;CH2(3-F-Ph),H],[ZA25;CH2(4-F-Ph),H],[ZA26;CH2(2-Cl-Ph),H],[ZA27;CH2(3-Cl-Ph),H],[ZA28;CH2(4-Cl-Ph),H],[ZA29;CH2(2-Br-Ph),H],[ZA30;CH2(3-Br-Ph),H],[ZA31;CH2(4-Br-Ph),H],[ZA32;CH2(2-Me-Ph),H],[ZA33;CH2(3-Me-Ph),H],[ZA34;CH2(4-Me-Ph),H],[ZA35;CH2(2-Et-Ph),H],[ZA36;CH2(3-Et-Ph),H],[ZA37;CH2(4-Et-Ph),H],[ZA38;CH2(2-t-Bu-Ph),H],[ZA39;CH2(3-t-Bu-Ph),H],[ZA40;CH2(4-t-Bu-Ph),H],[ZA41;CH2(2-CF3-Ph),H],[ZA42;CH2(3-CF3-Ph),H],[ZA43;CH2(4-CF3-Ph),H],[ZA44;CH2(2-OMe-Ph),H],[ZA45;CH2(3-OMe-Ph),H],[ZA46;CH2(4-OMe-Ph),H],[ZA47;CH2(2-SMe-Ph),H],[ZA48;CH2(3-SMe-Ph),H],[ZA49;CH2(4-SMe-Ph),H],[ZA50;CH2(2-CN-Ph),H],[ZA51;CH2(3-CN-Ph),H],[ZA52;CH2(4-CN-Ph),H],[ZA53;CH2(2,4-F2-Ph),H],[ZA54;CH2(2,5-F2-Ph),H],[ZA55;CH2(3,4-F2-Ph),H],[ZA56;CH2(3,5-F2-Ph),H],[ZA57;CH2(2 ,4-Cl2-Ph),H],[ZA58;CH2(2,5-Cl2-Ph),H],[ZA59;CH2(3,4-Cl2-Ph),H],[ZA60;CH2(3,5-Cl2-Ph),H],[ZA61;CH2(2,4-Me2-Ph),H],[ZA62;CH2 (2,5-Me2-Ph),H],[ZA63;CH2(3,4-Me2-Ph),H],[ZA64;CH2(3,5-Me2-Ph),H],[ZA65;CH2(2-F-4-Cl-Ph),H],[ZA66;CH2(2-Cl-4-F-Ph),H],[ZA67 ;CH2(2-F-4-Me-Ph),H],[ZA68;CH2(2-Me-4-F-Ph),H],[ZA69;CH2(2-F-4-OMe-Ph),H],[ZA70;CH2(2-OMe-4-F-Ph),H],[ZA71;CH2(2-Me-4-Cl-Ph ),H],[ZA72;CH2(2-Cl-4-Me-Ph),H],[ZA73;CH2(2-Me-4-OMe-Ph),H],[ZA74;CH2(2-OMe-4-Me-Ph),H],[ZA75;CH2(2-Cl-4-OMe-Ph),H],[ZA76;C H2(2-OMe-4-Cl-Ph),H],[ZA77;CH2(2,4,6-F3-Ph),H],[ZA78;CH2(3,4,5-F3-Ph),H],[ZA79;CH2(2-pyridyl),H],[ZA80;CH2(3-pyridyl),H],[ZA81;CH2( [4-pyridinyl),H],[ZA82; CH2(3-F-pyridin-2-yl),H],[ZA83; CH2(4-F-pyridin-2-yl),H],[ZA84; CH2(5-F-pyridin-2-yl),H],[ZA85; CH2(6-F-pyridin-2-yl),H],[ZA86; CH2(3-Cl-pyridin-2-yl),H],[ZA87; CH2(4-Cl-pyridin-2-yl),H],[ZA88; CH2(5-Cl-pyridin-2-yl),H],[ZA89; CH2(6-Cl-pyridin-2-yl),H],[ZA90; CH2(3-Me-pyridin-2-yl),H],[ZA91;[CH2(4-Me-pyridin-2-yl),H],[ZA92;CH2(5-Me-pyridin-2-yl),H],[ZA93;CH2(6-Me-pyridin-2-yl),H],[ZA94;CH2(3-OMe-pyridin-2-yl),H],[ZA95;CH2(4-OMe-pyridin-2-yl),H],[ZA96;CH2(5-OMe-pyridin-2-yl),H],[ZA97;CH2(6-OMe-pyridin-2-yl),H],[ZA98;CH2(3-CF3-pyridin-2-yl),H],[ZA99;CH2(4-CF3-pyridin-2-yl),H],[ZA100;CH2 [(5-CF3-pyridin-2-yl),H],[ZA101;CH2(6-CF3-pyridin-2-yl),H],[ZA102;CH2(3-CN-pyridin-2-yl),H],[ZA103;CH2(4-CN-pyridin-2-yl),H],[ZA104;CH2(5-CN-pyridin-2-yl),H],[ZA105;CH2(6-CN-pyridin-2-yl),H],[ZA106;CH2(2-F-pyridin-3-yl),H],[ZA107;CH2(4-F-pyridin-3-yl),H],[ZA108;CH2(5-F-pyridin-3-yl),H],[ZA109;CH2(6-CF3-pyridin-2-yl),H] [ZA110; CH2(2-Cl-pyridin-3-yl), H], [ZA111; CH2(4-Cl-pyridin-3-yl), H], [ZA112; CH2(5-Cl-pyridin-3-yl), H], [ZA113; CH2(6-Cl-pyridin-3-yl), H], [ZA114; CH2(2-Me-pyridin-3-yl), H], [ZA115; CH2(4-Me-pyridin-3-yl), H], [ZA116; CH2(5-Me-pyridin-3-yl), H], [ZA117; CH2(6-Me-pyridin-3-yl), H], [ZA118; CH2(2-O-F-pyridin-3-yl), H], [ZA119; CH2(2-Cl-pyridin-3-yl), H], [ZA110; CH2(2-Cl-pyridin-3-yl), H], [ZA111; CH2(4-Cl-pyridin-3-yl), H], [ZA111; CH2(2-O-F-pyridin-3-yl), H], [ZA111; CH2(2-Cl ... [ZA119; CH2(4-OMe-pyridin-3-yl), H], [ZA120; CH2(5-OMe-pyridin-3-yl), H], [ZA121; CH2(6-OMe-pyridin-3-yl), H], [ZA122; CH2(2-CF3-pyridin-3-yl), H], [ZA123; CH2(4-CF3-pyridin-3-yl), H], [ZA124; CH2(5-CF3-pyridin-3-yl), H], [ZA125; CH2(6-CF3-pyridin-3-yl), H], [ZA126; CH2(2-CN-pyridin-3-yl), H], [ZA127;CH2(4-CN-pyridin-3-yl),H],[ZA128;CH2(5-CN-pyridin-3-yl),H],[ZA129;CH2(6-CN-pyridin-3-yl),H],[ZA130;CH2(2-F-pyridin-4-yl),H],[ZA131;CH2(3-F-pyridin-4-yl),H],[ZA132;CH2(2-Cl-pyridin-4-yl),H],[ZA133;CH2(3- [Cl-pyridin-4-yl),H],[ZA134;CH2(2-Me-pyridin-4-yl),H],[ZA135;CH2(3-Me-pyridin-4-yl),H],[ZA136;CH2(2-OMe-pyridin-4-yl),H],[ZA137;CH2(3-OMe-pyridin-4-yl),H],[ZA138;CH2(2-CF3-pyridin-4-yl),H],[ZA139;CH2(3-CF [3-pyridin-4-yl),H],[ZA140; CH2(2-CN-pyridin-4-yl),H],[ZA141; CH2(3-CN-pyridin-4-yl),H],[ZA142; CH2(2-thienyl),H],[ZA143; CH2(3-thienyl),H],[ZA144; CH2(2-pyrimidinyl),H],[ZA145; CH2(4-pyrimidinyl),H],[ZA146; CH2(5-pyrimidinyl) [ZA147; CH2(3-pyridazinyl), H], [ZA148; CH2(4-pyridazinyl), H], [ZA149; CH2(4-Me-thiazolyl), H], [ZA150; CH2(4-Cl-thiazolyl), H], [ZA151; CH2(5-Me-thiazolyl), H], [ZA152; CH2(5-Cl-thiazolyl), H], [ZA153; (CH; 22 Ph,H],[ZA154;(CH 23Ph,H],[ZA155; CH2OMe,H],[ZA156; CH2OEt,H],[ZA157; CH2OPr,H],[ZA158; CH2OPh,H],[ZA159; CH2CN,H],[ZA160; Ph,H],[ZA161; 2-F-Ph,H],[ZA162; 3-F-Ph,H],[ZA163; 4-F-Ph,H],[ZA164; 2-Cl-Ph,H],[ZA165; 3-Cl-Ph,H],[ZA166; 4-Cl-Ph,H],[ZA167; 2-Me-Ph,H],[ZA168; 3-Me-Ph,H],[ZA169; 4-Me-Ph,H],[ZA170; 2-OMe-Ph,H],[ZA171; 3-OMe-Ph,H],[ZA172; 4-OMe-Ph,H],[ZA173; 2-pyridyl,H],[ZA174; 3-pyridyl,H],[ZA175; 4-pyridyl,H],[ZA176; 2-thienyl,H],[ZA177; 3-thienyl,H],[ZA178; 2-pyrimidinyl,H],[ZA179; 4-pyrimidinyl,H],[ZA180; 5-pyrimidinyl,H],[ZA181; 3-pyrazinyl,H],[ZA182; 4-pyrazinyl,H],[ZA183; Me,Me],[ZA184; Et,Me],[ZA185; Pr,Me],[ZA186; Bu,Me],[ZA187; Pen,Me],[ZA188; Hex,Me],[ZA189; i-Pr,Me],[ZA190; i-Bu,Me],[ZA191; t-Bu,Me],[ZA192; c-Pr,Me],[ZA193; c-Bu,Me],[ZA194; c-Pen,Me],[ZA195; c-Hex,Me],[ZA196; CH2c-Pr,Me],[ZA197; CH2c-Pen,Me],[ZA198; CH2c-Hex,Me],[ZA199; CH2CH=CH2,Me],[ZA200; CH2CH=CHMe,Me],

[0810] [ZA201;CH2CH=CMe2,Me],[ZA202;CH2C≡CH,Me],[ZA203;CH2C≡CMe,Me],[ZA204;CH2Ph,Me],[ZA205;CH2(2-F-Ph),Me],[ZA206;CH2(3-F-Ph),Me],[ZA207;CH2(4-F-Ph),Me],[ZA208;CH2(2-Cl-Ph),Me],[ZA209;CH2(3-Cl-Ph),Me],[ZA210;CH2(4-Cl-Ph),Me],[ZA211;CH2(2-Br-Ph),Me],[ZA212;CH2(3-Br-Ph),Me],[ZA213;CH2(4-Br-Ph),Me],[ZA214;CH2(2-Me-Ph),Me],[ZA215;CH2(3-Me-Ph),Me],[ZA216;CH2(4-Me-Ph),Me],[ZA217;CH2(2-Et-Ph),Me],[ZA218;CH2(3-Et-Ph),Me],[ZA219;CH2(4-Et-Ph),Me],[ZA220;CH2(2-t-Bu-Ph),Me],[ZA221;CH2(3-t-Bu-Ph),Me],[ZA222;CH2(4-t-Bu-Ph),Me],[ZA223;CH2(2-CF3-Ph),Me],[ZA224;CH2(3-CF3-Ph),Me],[ZA225;CH2(4-CF3-Ph),Me],[ZA226;CH2(2-OMe-Ph),Me],[ZA227;CH2(3-OMe-Ph),Me],[ZA228;CH2(4-OMe-Ph),Me],[ZA229;CH2(2-SMe-Ph),Me],[ZA230;CH2(3-SMe-Ph),Me],[ZA231;CH2(4-SMe-Ph),Me],[ZA232;CH2(2-CN-Ph),Me],[ZA233;CH2(3-CN-Ph),Me],[ZA234;CH2(4-CN-Ph),Me],[ZA235;CH2(2,4-F2-Ph),Me],[ZA236;CH2(2,5-F2-Ph),Me],[ZA237;CH2(3,4-F2-Ph),Me],[ZA238;CH2(3,5-F2-Ph),Me],[ZA239;CH2(2,4-Cl2-Ph),Me],[ZA240;CH2(2,5-Cl2-Ph),Me],[ZA241;CH2(3,4-Cl2-Ph),Me],[ZA242;CH2(3,5-Cl2-Ph),Me],[ZA243;CH2(2,4-Me2-Ph),Me],[ZA244;CH2(2,5-Me2-Ph),Me],[ZA245;CH2(3,4-Me2-Ph), Me],[ZA246;CH2(3,5-Me2-Ph),Me],[ZA247;CH2(2-F-4-Cl-Ph),Me],[ZA248;CH2(2-Cl-4-F-Ph),Me],[ZA249;CH2(2-F-4-Me-Ph),Me],[ZA250;CH 2(2-Me-4-F-Ph),Me],[ZA251;CH2(2-F-4-OMe-Ph),Me],[ZA252;CH2(2-OMe-4-F-Ph),Me],[ZA253;CH2(2-Me-4-Cl-Ph),Me],[ZA254;CH2(2-Cl-4- Me-Ph),Me],[ZA255;CH2(2-Me-4-OMe-Ph),Me],[ZA256;CH2(2-OMe-4-Me-Ph),Me],[ZA257;CH2(2-Cl-4-OMe-Ph),Me],[ZA258;CH2(2-OMe-4-Cl-P [ZA259;CH2(2,4,6-F3-Ph),Me],[ZA260;CH2(3,4,5-F3-Ph),Me],[ZA261;CH2(2-pyridyl),Me],[ZA262;CH2(3-pyridyl),Me],[ZA263;CH2(4-pyridyl),Me],[ZA264;CH2(3-F-pyridin-2-yl),Me],[ZA265;CH2(4-F-pyridin-2-yl),Me],[ZA266;CH2(5-F-pyridin-2-yl),Me],[ZA267;CH2(6-F-pyridin-2-yl),Me],[ZA268;CH2( [3-Cl-pyridin-2-yl),Me],[ZA269; CH2(4-Cl-pyridin-2-yl),Me],[ZA270; CH2(5-Cl-pyridin-2-yl),Me],[ZA271; CH2(6-Cl-pyridin-2-yl),Me],[ZA272; CH2(3-Me-pyridin-2-yl),Me],[ZA273; CH2(4-Me-pyridin-2-yl),Me],[ZA274; CH2(5-Me-pyridin-2-yl),Me],[ZA275; CH2(6-Me-pyridin-2-yl),Me],[ZA276; CH2(3-OMe-pyridin-2-yl),Me],[ZA277;[CH2(4-OMe-pyridin-2-yl),Me],[ZA278;CH2(5-OMe-pyridin-2-yl),Me],[ZA279;CH2(6-OMe-pyridin-2-yl),Me],[ZA280;CH2(3-CF3-pyridin-2-yl),Me],[ZA281;CH2(4-CF3-pyridin-2-yl),Me],[ZA282;CH2(5-CF3-pyridin-2-yl),Me],[ZA283;CH2(6-CF3-pyridin-2-yl),Me],[ZA284;CH2(3-CN-pyridin-2-yl),Me],[ZA285;CH2(4-CN-pyridin-2-yl) [ZA286; CH2(5-CN-pyridin-2-yl),Me], [ZA287; CH2(6-CN-pyridin-2-yl),Me], [ZA288; CH2(2-F-pyridin-3-yl),Me], [ZA289; CH2(4-F-pyridin-3-yl),Me], [ZA290; CH2(5-F-pyridin-3-yl),Me], [ZA291; CH2(6-F-pyridin-3-yl),Me], [ZA292; CH2(2-Cl-pyridin-3-yl),Me], [ZA293; CH2(4-Cl-pyridin-3-yl),Me], [ZA294; CH2(5-Cl-pyridin-3-yl)] [ZA295; CH2(6-Cl-pyridin-3-yl),Me],[ZA296; CH2(2-Me-pyridin-3-yl),Me],[ZA297; CH2(4-Me-pyridin-3-yl),Me],[ZA298; CH2(5-Me-pyridin-3-yl),Me],[ZA299; CH2(6-Me-pyridin-3-yl),Me],[ZA300; CH2(2-OMe-pyridin-3-yl),Me],[ZA301; CH2(4-OMe-pyridin-3-yl),Me],[ZA302; CH2(5-OMe-pyridin-3-yl),Me],[ZA303; CH2(6-OMe [ZA304; CH2(2-CF3-pyridin-3-yl),Me], [ZA305; CH2(4-CF3-pyridin-3-yl),Me], [ZA306; CH2(5-CF3-pyridin-3-yl),Me], [ZA307; CH2(6-CF3-pyridin-3-yl),Me], [ZA308; CH2(2-CN-pyridin-3-yl),Me], [ZA309; CH2(4-CN-pyridin-3-yl),Me], [ZA310; CH2(5-CN-pyridin-3-yl),Me], [ZA311; CH2(6-CN-pyridin-3-yl),Me], [ZA312;[CH2(2-F-pyridin-4-yl),Me],[ZA313;CH2(3-F-pyridin-4-yl),Me],[ZA314;CH2(2-Cl-pyridin-4-yl),Me],[ZA315;CH2(3-Cl-pyridin-4-yl),Me],[ZA316;CH2(2-Me-pyridin-4-yl),Me],[ZA317;CH2(3-Me-pyridin-4-yl),Me],[ZA318;CH2(2-Me-pyridin-4-yl),Me],[ZA319;CH2(2-Me-pyridin-4-yl),Me],[ZA312;CH2(2-F-pyridin-4-yl),Me],[ZA312;CH2(2-F-pyridin-4-yl),Me],[ZA313;CH2(2-F-pyridin-4-yl),Me],[ZA314;CH2(2-Cl-pyridin-4-yl),Me],[ZA315;CH2(3-Cl-pyridin-4-yl),Me],[ZA316;CH2(2-Me-pyridin-4-yl),Me],[ZA317;CH2(2-Me-pyridin-4-yl),Me],[ZA319;CH2(2-F-pyridin-4-yl),Me],[ZA312;CH2(2-F-pyridin-4-yl),Me],[ZA313;CH2(2-F-pyridin-4-yl),Me],[ZA314;CH2(2-F-pyridin-4-yl),Me],[ZA315;CH2(2-Cl-pyridin-4-yl),Me],[ZA316;CH2(2-Me-pyridin [ZA318; CH2(2-OMe-pyridin-4-yl),Me], [ZA319; CH2(3-OMe-pyridin-4-yl),Me], [ZA320; CH2(2-CF3-pyridin-4-yl),Me], [ZA321; CH2(3-CF3-pyridin-4-yl),Me], [ZA322; CH2(2-CN-pyridin-4-yl),Me], [ ZA323;CH2(3-CN-pyridin-4-yl),Me],[ZA324;CH2(2-thienyl),Me],[ZA325;CH2(3-thienyl),Me],[ZA326;CH2(2-pyrimidinyl),Me],[ZA327;CH2(4-pyrimidinyl),Me],[ZA328;CH2(5-pyrimidinyl),Me],[ZA329;CH2(3-pyridazine) [ZA330; CH2(4-pyridazinyl),Me], [ZA331; CH2(4-Me-thiazol-2-yl),Me], [ZA332; CH2(4-Cl-thiazol-2-yl),Me], [ZA333; CH2(5-Me-thiazol-2-yl),Me], [ZA334; CH2(5-Cl-thiazol-2-yl),Me], [ZA335; (CH; 22 Ph,Me],[ZA336;(CH 23Ph,Me],[ZA337;CH2OMe,Me],[ZA338;CH2OEt,Me],[ZA339;CH2OPr,Me],[ZA340;CH2OPh,Me],[ZA341;CH2CN,Me],[ZA342;Ph,Me],[ZA343;2-F-Ph,Me ],[ZA344;3-F-Ph,Me],[ZA345;4-F-Ph,Me],[ZA346;2-Cl-Ph,Me],[ZA347;3-Cl-Ph,Me],[ZA348;4-Cl-Ph,Me],[ZA349;2-Me-Ph,Me],[ZA350;3-Me-P [ZA351; 4-Me-Ph,Me], [ZA352; 2-OMe-Ph,Me], [ZA353; 3-OMe-Ph,Me], [ZA354; 4-OMe-Ph,Me], [ZA355; 2-pyridyl,Me], [ZA356; 3-pyridyl,Me], [ZA357; 4-pyridyl,Me], [ZA358; 2-thiophene,Me], [ZA359; 3-thiophene,Me], [ZA360; 2-pyrimidinyl,Me], [ZA361; 4-pyrimidinyl,Me], [ZA362; 5-pyrimidinyl,Me], [ZA363; 3-pyridazinyl,Me], [ZA364; 4-pyridazinyl,Me]

[0811] In compound (1A), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 For ethyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX2).

[0812] In compound (1A), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX3).

[0813] In compound (1A), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX4).

[0814] In compound (1A), X is CH, L is an oxygen atom, and R... 1 For methyl, RX2 It is a methoxy group, R 3 and R 4 It refers to any combination of compounds recorded in combination A (hereinafter referred to as compound group SX5).

[0815] In compound (1A), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is cyclopropyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX6).

[0816] In compound (1A), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X22 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX7).

[0817] In compound (1A), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX8).

[0818] In compound (1A), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX9).

[0819] In compound (1A), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX10).

[0820] In compound (1A), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX11).

[0821] In compound (1A), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom.X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX12).

[0822] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX13).

[0823] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 For ethyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX14).

[0824] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX15).

[0825] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX16).

[0826] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methoxy group, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX17).

[0827] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 It is cyclopropyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX18).

[0828] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1R is a fluorine atom. X2 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX19).

[0829] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX20).

[0830] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX21).

[0831] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX22).

[0832] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX23).

[0833] In compound (1A), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX24).

[0834] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX25).

[0835] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen.1 For methyl, R X2 For ethyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX26).

[0836] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX27).

[0837] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX28).

[0838] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 It is a methoxy group, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX29).

[0839] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 It is cyclopropyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX30).

[0840] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX31).

[0841] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX32).

[0842] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen.1 R is a fluorine atom. X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX33).

[0843] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 For methyl, R 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX34).

[0844] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 R is a fluorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX35).

[0845] In compound (1A), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 R is a chlorine atom. 3 and R 4 The compound is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX36).

[0846] In the compound represented by formula (1B) (hereinafter referred to as compound (1B)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X2 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX37).

[0847] [Chemical Formula 59]

[0848]

[0849] Group V: Composed of Me, Et, Pr, i-Pr, c-Pr, c-Bu, c-Pen, c-Hex, (CH2)3CH3, CH2CH(CH3)2, CH(CH3)CH2CH3, t-Bu, CH2c-Pr, (CH2)4CH3, (CH2)2CH(CH3)2, CH(CH3)(CH2)2CH3, CH(CH2CH3)CH2CH3, CH2CH(CH3)CH2CH3, C(CH3)2CH2CH3, CH2t-Bu, CH2c-Bu, CH2c-Pen, (CH2)2c-Pr, (1-methylcyclopropyl)methyl, (2-methylcyclopropyl)methyl, 1-cyclopropylethyl, (C H2)3c-Pr, (CH2)5CH3, (CH2)3CH(CH3)2, (CH2)2CH(CH3)CH2CH3, CH2CH(CH3)(CH2)2CH3, CH(CH3)(CH2)3CH3, CH2CH(CH2CH3)2, heptyl, 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、CH 2C(CH3)=CHCH2CH3、CH2CF=CH2、CH2CF=CHCH3、CH2CF=C(CH3)2、CH2CF=CF2、CH2CF=CHCH2CH3、CH2CF=CH(CH2)2CH3、CH2CCl=CH2、CH2CCl=CHCH3、CH2C Cl=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)3CH=CH2, (CH2)3C(CH3)=CH2, (CH2)4CH=CH2, CH2C≡CH, CH2C≡CCH3, CH2C≡CCH2CH3, CH2C≡Cc-Pr, (CH2)2C≡ CH, (CH2)2C≡CCH3, (CH2)2C≡CCH2CH3, (CH2)3C≡CH, (CH2)3C≡CCH3, CH2Cl, CH2Br, CH2OCH3, CH2OCH2CH3, CH2O(CH2)2CH3, CHF2, CF3, CH2CF3, CH2CHF2,CH2CH2CHF2, CH2CH2CF3, CH2CF2CF3, (CH2)2CF2CF3, CH2(CF2)2CF3, (CH2)2CF(CF3)2, (CH2)2(CF2)5CF3, CF3, CF2CHF(CF3), CF2CHF(OCF3), CH2CF2CF2H, Ph, 2-F-Ph, 3-F-Ph, The group consisting of 4-F-Ph, 2-Cl-Ph, 3-Cl-Ph, 4-Cl-Ph, 2-Me-Ph, 3-Me-Ph, 4-Me-Ph, 2-OMe-Ph, 3-OMe-Ph, 4-OMe-Ph, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 3-pyridazinyl, and 4-pyridazinyl.

[0850] In compound (1B), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 For ethyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX38).

[0851] In compound (1B), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX39).

[0852] In compound (1B), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX40).

[0853] In compound (1B), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methoxy group, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX41).

[0854] In compound (1B), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is cyclopropyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX42).

[0855] In compound (1B), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom.X2 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX43).

[0856] In compound (1B), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX44).

[0857] In compound (1B), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX45).

[0858] In compound (1B), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX46).

[0859] In compound (1B), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX47).

[0860] In compound (1B), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX48).

[0861] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX49).

[0862] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 For ethyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX50).

[0863] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX51).

[0864] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX52).

[0865] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methoxy group, R 5 SX53 is a compound selected from group V with any substituents (hereinafter, group SX53 is denoted as SX53).

[0866] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 It is cyclopropyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX54).

[0867] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX55).

[0868] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX56).

[0869] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX57).

[0870] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For methyl, R 5The compound is selected from group V with any substituents (hereinafter referred to as compound group SX58).

[0871] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX59).

[0872] In compound (1B), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX60).

[0873] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX61).

[0874] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 For ethyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX62).

[0875] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX63).

[0876] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX64).

[0877] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 It is a methoxy group, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX65).

[0878] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, RX2 It is cyclopropyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX66).

[0879] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX67).

[0880] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX68).

[0881] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX69).

[0882] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX70).

[0883] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX71).

[0884] In compound (1B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX72).

[0885] In the compound represented by formula (2B) (hereinafter referred to as compound (2B)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X28 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX73).

[0886] [Chemical Formula 60]

[0887]

[0888] In compound (2B), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX74).

[0889] In compound (2B), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX75).

[0890] In compound (2B), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 It is a methoxy group, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX76).

[0891] In compound (2B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX77).

[0892] In compound (2B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX78).

[0893] In compound (2B), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX79).

[0894] In compound (2B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X28 For methyl, R 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX80).

[0895] In compound (2B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X28 R is a fluorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX81).

[0896] In compound (2B), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X28 R is a chlorine atom. 5 The compound is selected from group V with any substituents (hereinafter referred to as compound group SX82).

[0897] In the compound represented by formula (1C) (hereinafter referred to as compound (1C)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X2 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX83).

[0898] [Chemical Formula 61]

[0899]

[0900] Group Y: Composed of 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、CH 2C(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=CHCH2CH 3. (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≡CCH2C H3, 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≡CCH2CH 3. (CH2)3C≡Cc-Pr, (CH2)3C≡CPh, CH2Cl, CH2Br, CH2CN, CH2OCH3, CH2OCH2CH3 , CH2O(CH2)2CH3, CH2SCH3, CH2SCH2CH3, CH2S(CH2)2CH3, 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-oxacyclopropyl), CH2(2-tetrahydrofuranyl), CH2(2-tetrahydropyranyl)

[0901] CH2CH=NOCH3, CH2CH=NOCH2CH3, CH2CH=NOCH2Ph, CH2

[0902] C(CH3)=NOCH3、CH2C(CH3)=NOCH2CH3、CH2C(CH3)=NOCH2Ph、(CH2)2F、CH2C F3、(CH2)2Cl、CH2CCl3、(CH2)2Br、(CH2)2I、(CH2)2CF3、(CH2)2CN、(CH2)2N O2、(CH2)2OCH3、(CH2)2OCH2CH3、(CH2)2SCH3、(CH2)2SCH2CH3、(CH2)2SPh 、(CH2)2NHCH3、(CH2)2N(CH3)2、(CH2)2NHPh、(CH2)2NHCH2Ph、(CH2)2N(CH3 )CH2Ph、(CH2)2C(O)CH3、(CH2)2C(O)CH2CH3、(CH2)2C(O)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)CH2CH3、(CH2)2NHC(O)Ph、(CH2)2NCH3C(O)CH3、(CH2)2NCH3C(O)CH 2CH3, (CH2)2NCH3C(O)Ph, (CH2)2NHC(O)OCH3, (CH2)2NHC(O)OCH2CH3, (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(C H3)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, (CH2 )3F, (CH2)3Cl, (CH2)3Br, (CH2)3I, (CH2)3CF3, (CH2)3CN, (CH2)3NO2, (CH2)3OCH3, (CH2)3OCH2CH3, (CH2 )3SCH3, (CH2)3SCH2CH3, (CH2)3NHCH3, (CH2)3N(CH3)2, (CH2)4F, (CH2)4Cl, (CH2)4CF3, (CH2)4CN, (CH2) 4NO2, (CH2)4Ph, (CH2)4OCH3, (CH2)4SCH3, (CH2)4NHCH3, (CH2)4N(CH3)2, (CH2)5F, (CH2)5Cl, (CH2)5CF3 , (CH2)5CN, (CH2)5NO2, (CH2)5Ph, (CH2)5OCH3, (CH2)5SCH3, (CH2)5NHCH3, (CH2)5N(CH3)2, (CH2)6F, (CH 2) A group consisting of 6Cl, (CH2)6CF3, (CH2)6CN, (CH2)6NO2, (CH2)6Ph, (CH2)6OCH3, (CH2)6SCH3, (CH2)6NHCH3, (CH2)6N(CH3)2, CH2CF2CF3, (CH2)2CF2CF3, CH2(CF2)2CF3, (CH2)2CF(CF3)2, (CH2)2(CF2)5CF3, CF3, CHF2, and CH2F.

[0903] In compound (1C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 For ethyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX84).

[0904] In compound (1C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX85).

[0905] In compound (1C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX86).

[0906] In compound (1C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methoxy group, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX87).

[0907] In compound (1C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is cyclopropyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX88).

[0908] In compound (1C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX89).

[0909] In compound (1C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX90).

[0910] In compound (1C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX91).

[0911] In compound (1C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX92).

[0912] In compound (1C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX93).

[0913] In compound (1C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX94).

[0914] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX95).

[0915] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 For ethyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX96).

[0916] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX97).

[0917] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX98).

[0918] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methoxy group, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX99).

[0919] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 It is cyclopropyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX100).

[0920] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 For methyl, R 6The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX101).

[0921] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX102).

[0922] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX103).

[0923] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX104).

[0924] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX105).

[0925] In compound (1C), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX106).

[0926] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX107).

[0927] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 For ethyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX108).

[0928] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1For methyl, R X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX109).

[0929] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX110).

[0930] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 It is a methoxy group, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX111).

[0931] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 It is cyclopropyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX112).

[0932] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX113).

[0933] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX114).

[0934] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX115).

[0935] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX116).

[0936] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX117).

[0937] In compound (1C), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX118).

[0938] In the compound represented by formula (2C) (hereinafter referred to as compound (2C)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X2 Methyl group, m = 2, R X3 R X4 R X5 R X6 and R X7 It refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX119).

[0939] [Chemical Formula 62]

[0940]

[0941] Combination B consists of substituents numbered ZB1 to ZB306. Substituents numbered ZB1 to ZB306 refer to R in compound (2C), the compound represented by formula (1D), and the compound represented by formula (2D). X3 R X4 R X5 R X6 and R X7 The combination of [substituent number; R] is denoted below as [substituent number; R]. X3 ,R X4 ,R X5 ,R X6 ,R X7 For example, the substituent number ZB2 refers to R. X3 It is methyl and R X4 R X5 R X6 and R X7 It is a combination of hydrogen atoms.

[0942] Combination B

[0943] [ZB1;H,H,H,H,H],[ZB2;Me,H,H,H,H],[ZB3;F,H,H,H,H],[ZB4;Cl,H,H,H,H],[ZB5;OMe,H,H,H,H],[ZB6;CF3,H,H,H,H],[ZB7;H,Me,H,H,H],[ZB8;H,Et,H,H,H],[ZB9;H,Pr,H,H,H],[ZB10;H,i-Pr,H,H,H],[ZB11;H,t-Bu,H,H,H],[ZB12;H,OMe,H,H,H],[ZB13;H,OEt,H,H,H],[ZB14;H,OPr,H,H,H],[ZB15;H,Oi-Pr,H,H,H],[ZB16;H,CF3,H,H,H],[ZB17;H,CF2H,H,H,H],[ZB18;H,CFH2,H,H,H],[ZB19;H,F,H,H,H],[ZB20;H,Cl,H,H,H],[ZB21;H,Br,H,H,H],[ZB22;H,CN,H,H,H],[ZB23;H,Ph,H,H,H],[ZB24;H,OPh,H,H,H],[ZB25;H,c-Pr,H,H,H],[ZB26;H,c-Pen,H,H,H],[ZB27;H,c-Hex,H,H,H],[ZB28;H,H,Me,H,H],[ZB29;H,H,Et,H,H],[ZB30;H,H,Pr,H,H],[ZB31;H,H,i-Pr,H,H],[ZB32;H,H,t-Bu,H,H],[ZB33;H,H,OMe,H,H],[ZB34;H,H,OEt,H,H],[ZB35;H,H,OPr,H,H],[ZB36;H,H,Oi-Pr,H,H],[ZB37;H,H,CF3,H,H],[ZB38;H,H,CF2H,H,H],[ZB39;H,H,CFH2,H,H],[ZB40;H,H,F,H,H],[ZB41;H,H,Cl,H,H],[ZB42;H,H,Br,H,H],[ZB43;H,H,CN,H,H],[ZB44;H,H,Ph,H,H],[ZB45;H,H,OPh,H,H],[ZB46;H,H,c-Pr,H,H],[ZB47;H,H,c-Pen,H,H],[ZB48;H,H,c-Hex,H,H],[ZB49;Me,H,H,H,F],[ZB50;F,H,H,H,F],[ZB51;Cl,H,H,H,F],[ZB52;H,Me,H,H,F],[ZB53;H,Et,H,H,F],[ZB54;H,Pr,H,H,F],[ZB55;H,i-Pr,H,H,F],[ZB56;H,t-Bu,H,H,F],[ZB57;H,OMe,H,H,F],[ZB58;H,OEt,H,H,F],[ZB59;H,OPr,H,H,F],[ZB60;H,Oi-Pr,H,H,F],[ZB61;H,CF3,H,H,F],[ZB62;H,CF2H,H,H,F],[ZB63;H,CFH2,H,H,F],[ZB64;H,F,H,H,F],[ZB65;H,Cl,H,H,F],[ZB66;H,Br,H,H,F],[ZB67;H,CN,H,H,F],[ZB68;H,Ph,H,H,F],[ZB69;H,OPh,H,H,F],[ZB70;H,c-Pr,H,H,F],[ZB71;H,c-Pen,H,H,F],[ZB72;H,c-Hex,H,H,F],[ZB73;H,H,Me,H,F],[ZB74;H,H,Et,H,F],[ZB75;H,H,Pr,H,F],[ZB76;H,H,i-Pr,H,F],[ZB77;H,H,t-Bu,H,F],[ZB78;H,H,OMe,H,F],[ZB79;H,H,OEt,H,F],[ZB80;H,H,OPr,H,F],[ZB81;H,H,Oi-Pr,H,F],[ZB82;H,H,CF3,H,F],[ZB83;H,H,CF2H,H,F],[ZB84;H,H,CFH2,H,F],[ZB85;H,H,F,H,F],[ZB86;H,H,Cl,H,F],[ZB87;H,H,Br,H,F],[ZB88;H,H,CN,H,F],[ZB89;H,H,Ph,H,F],[ZB90;H,H,OPh,H,F],[ZB91;H,H,c-Pr,H,F],[ZB92;H,H,c-Pen,H,F],[ZB93;H,H,c-Hex,H,F],[ZB94;Me,H,H,H,Cl],[ZB95;F,H,H,H,Cl],[ZB96;Cl,H,H,H,Cl],[ZB97;H,Me,H,H,Cl],[ZB98;H,Et,H,H,Cl],[ZB99;H,Pr,H,H,Cl],[ZB100;H,i-Pr,H,H,Cl],[ZB101;H,t-Bu,H,H,Cl],[ZB102;H,OMe,H,H,Cl],[ZB103;H,OEt,H,H,Cl],[ZB104;H,OPr,H,H,Cl],[ZB105;H,Oi-Pr,H,H,Cl],[ZB106;H,CF3,H,H,Cl],[ZB107;H,CF2H,H,H,Cl],[ZB108;H,CFH2,H,H,Cl],[ZB109;H,F,H,H,Cl],[ZB110;H,Cl,H,H,Cl],[ZB111;H,Br,H,H,Cl],[ZB112;H,CN,H,H,Cl],[ZB113;H,Ph,H,H,Cl],[ZB114;H,OPh,H,H,Cl],[ZB115;H,c-Pr,H,H,Cl],[ZB116;H,c-Pen,H,H,Cl],[ZB117;H,c-Hex,H,H,Cl],[ZB118;H,H,Me,H,Cl],[ZB119;H,H,Et,H,Cl],[ZB120;H,H,Pr,H,Cl],[ZB121;H,H,i-Pr,H,Cl],[ZB 122;H,H,t-Bu,H,Cl],[ZB123;H,H,OMe,H,Cl],[ZB124;H,H,OEt,H,Cl],[ZB125;H,H,OPr,H,Cl],[ZB126;H,H,Oi-Pr,H,Cl],[ZB127;H,H,CF3,H,Cl],[ZB128;H,H,CF2H,H,Cl],[ZB129;H,H,CFH2,H,Cl],[ZB130;H,H,F,H,Cl],[ZB131;H,H,Cl,H,Cl],[ZB132;H,H,Br,H,Cl],[ZB133;H,H,CN,H,Cl],[ZB134;H,H,Ph,H,Cl],[ZB135;H,H,OPh,H,Cl],[ZB136;H,H,c-Pr,H,Cl],[ZB137;H,H,c-Pen,H,Cl],[ZB138;H,H,c-Hex,H,Cl],[ZB139;Me,H,H,H,Me],[ZB140;F,H,H,H,Me],[ZB141;Cl,H,H,H,Me],[ZB142;H,Me,H,H,Me],[ZB143;H,Et,H,H,Me],[ZB144;H,Pr,H,H,Me],[ZB145;H,i-Pr,H,H,Me],[ZB146;H,t-Bu,H,H,Me],[ZB147;H,OMe,H,H,Me],[ZB148;H,OEt,H,H,Me],[ZB149;H,OPr,H,H,Me],[ZB150;H,Oi-Pr,H,H,Me],;

[0944] [ZB151;H,CF3,H,H,Me],[ZB152;H,CF2H,H,H,Me],[ZB153;H,CFH2,H,H,Me],[ZB154;H,F,H,H,Me],[ZB155;H,Cl,H,H,Me],[ZB156;H,Br,H,H,Me],[ZB157;H,CN,H,H,Me],[ZB158;H,Ph,H,H,Me],[ZB159;H,OPh,H,H,Me],[ZB 160;H,c-Pr,H,H,Me],[ZB161;H,c-Pen,H,H,Me],[ZB162;H,c-Hex,H,H,Me],[ZB163;H,H,Me,H,Me],[ZB164;H,H,Et,H,Me],[ZB165;H,H,Pr,H,Me],[ZB166;H,H,i-Pr,H,Me],[ZB167;H,H,t-Bu,H,Me],[ZB168;H,H,OMe,H,Me],[ZB169;H,H,OEt,H,Me],[ZB170;H,H,OPr,H,Me],[ZB171;H,H,Oi-Pr,H,Me],[ZB172;H,H,CF3,H,Me],[ZB173;H,H,CF2H,H,Me],[ZB174;H,H,CFH2,H,Me],[ZB175;H,H,F,H,Me],[ZB176;H,H,Cl,H,Me],[ZB177;H,H,Br,H,Me],[ZB178;H,H,CN,H,Me],[ZB179;H,H,Ph,H,Me],[ZB180;H,H,OPh,H,Me],[ZB181;H,H,c-Pr,H,Me],[ZB182;H,H,c-Pen,H,Me],[ZB183;H,H,c-Hex,H,Me],[ZB184;Me,H,H,H,OMe],[ZB185;F,H,H,H,OMe],[ZB186;Cl,H,H,H,OMe],[ZB187;H,Me,H,H,OMe],[ZB188;H,Et,H,H,OMe],[ZB189;H,Pr,H,H,OMe],[ZB190;H,i-Pr,H,H,OMe],[ZB191;H,t-Bu,H,H,OMe],[ZB192;H,OMe,H,H,OMe],[ZB193;H,OEt,H,H,OMe],[ZB194;H,OPr,H,H,OMe],[ZB195;H,Oi-Pr,H,H,OMe],[ZB196;H,CF3,H,H,OMe],[ZB 197;H,CF2H,H,H,OMe],[ZB198;H,CFH2,H,H,OMe],[ZB199;H,F,H,H,OMe],[ZB200;H,Cl,H,H,OMe],[ZB201;H,Br,H,H,OMe],[ZB202;H,CN,H,H,OMe],[ZB203;H,Ph,H,H,OMe],[ZB204;H,OPh,H,H,OMe],[ZB205;H,c-Pr,H,H,OMe],[ZB206;H,c-Pen,H,H,OMe],[ZB207;H,c-Hex,H,H,OMe],[ZB208;H,H,Me,H,OMe],[ZB209;H,H,Et,H,OMe],[ZB210;H,H,Pr,H,OMe],[ZB211;H,H,i-Pr,H,OMe],[ZB212;H,H,t-Bu,H,OMe],[ZB213;H,H,OMe,H,OMe],[ZB214;H,H,OEt,H,OMe],[ZB215;H,H,OPr,H,OMe],[ZB216;H,H,Oi-Pr,H,OMe],[ZB217;H,H,CF3,H,OMe],[ZB218;H,H,CF2H,H,OMe],[ZB219;H,H,CFH2,H,OMe],[ZB220;H,H,F,H,OMe],[ZB221;H,H,Cl,H,OMe],[ZB222;H,H,Br,H,OMe],[ZB223;H,H,CN,H,OMe],[ZB224;H,H,Ph,H,OMe],[ZB225;H,H,OPh,H,OMe],[ZB226;H,H,c-Pr,H,OMe],[ZB227;H,H,c-Pen,H,OMe],[ZB228;H,H,c-Hex,H,OMe],[ZB229;Me,H,H,H,CF3],[ZB230;F,H,H,H,CF3],[ZB231;Cl,H,H,H,CF3],[ZB232;H,Me,H,H,CF3],[ZB233;H,Et,H,H,CF3],[ZB234;H,Pr,H,H,CF3],[ZB235;H,i-Pr,H,H,CF3],[ZB236;H,t-Bu,H,H,CF3],[ZB237;H,OMe,H,H,CF3],[ZB238;H,OEt,H,H,CF3],[ZB239;H,OPr,H,H,CF3],[ZB240;H,Oi-Pr,H,H,CF3],[ZB241;H,CF3,H,H,CF3],[ZB242;H,CF2H,H,H,CF3],[ZB243;H,CFH2,H,H,CF3],[ZB244;H,F,H,H,CF3],[ZB245;H,Cl,H,H,CF3],[ZB246;H,Br,H,H,CF3],[ZB247;H,CN,H,H,CF3],[ZB248;H,Ph,H,H,CF3],[ZB249;H,OPh,H,H,CF3],[ZB250;H,c-Pr,H,H,CF3],[ZB251;H,c-Pen,H,H,CF3],[ZB252;H,c-Hex,H,H,CF3],[ZB253;H,H,Me,H,CF3],[ZB254;H,H,Et,H,CF3],[ZB255;H,H,Pr,H,CF3],[ZB256;H,H,i-Pr,H,CF3],[ZB257;H,H,t-Bu,H,CF3],[ZB258;H,H,OMe,H,CF3],[ZB259;H,H,OEt,H,CF3],[ZB260;H,H,OPr,H,CF3],[ZB261;H,H,Oi-Pr,H,CF3],[ZB262;H,H,CF3,H,CF3],[ZB263;H,H,CF2H,H,CF3],[ZB264;H,H,CFH2,H,CF3],[ZB265;H,H,F,H,CF3],[ZB266;H,H,Cl,H,CF3],[ZB267;H,H,Br,H,CF3],[ZB268;H,H,CN,H,CF3],[ZB269;H,H,Ph,H,CF3],[ZB270;H,H,OPh,H,CF3],[ZB271;H,H,c-Pr,H,CF3],[ZB272;H,H,c-Pen,H,CF3],;

[0945] [ZB273;H,H,c-Hex,H,CF3],[ZB274;H,F,F,H,H],[ZB275;H,F,H,F,H],[ZB276;H,F,F,F,H],[ZB277 ;F,F,F,H,H],[ZB278;F,F,H,F,H],[ZB279;F,H,F,H,F],[ZB280;F,F,F,F,F],[ZB281;H,Cl,H,Cl,H] ,[ZB282;H,OMe,H,OMe,H],[ZB283;H,F,Cl,H,H],[ZB284;H,F,Me,H,H],[ZB285;H,F,OMe,H,H],[ZB2 86;H,F,CF3,H,H],[ZB287;H,Cl,F,H,H],[ZB288;H,Cl,Cl,H,H],[ZB289;H,Cl,Me,H,H],[ZB290;H,C l,OMe,H,H],[ZB291;H,Cl,CF3,H,H],[ZB292;H,Me,F,H,H],[ZB293;H,Me,Cl,H,H],[ZB294;H,Me,Me ,H,H],[ZB295;H,Me,OMe,H,H],[ZB296;H,Me,CF3,H,H],[ZB297;H,OMe,F,H,H],[ZB298;H,OMe,Cl,H ,H],[ZB299;H,OMe,Me,H,H],[ZB300;H,OMe,OMe,H,H],[ZB301;H,OMe,CF3,H,H],[ZB302;H,CF3,F,H ,H],[ZB303;H,CF3,Cl,H,H],[ZB304;H,CF3,F,H,H],[ZB305;H,CF3,Cl,H,H],[ZB306;H,CF3,F,H,H]

[0946] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 For fluorine atoms, m is 2, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX120).

[0947] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 For chlorine atoms, m is 2, R X3 R X4 RX5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX121).

[0948] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For fluorine atoms, m is 2, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX122).

[0949] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For chlorine atoms, m is 2, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX123).

[0950] In compound (2C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methyl group, m is 3, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX124).

[0951] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 It is a fluorine atom, m is 3, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX125).

[0952] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 It is a chlorine atom, m is 3, R X3 R X4 R X5 R X6 and RX7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX126).

[0953] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 It is a fluorine atom, m is 3, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX127).

[0954] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 It is a chlorine atom, m is 3, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX128).

[0955] In compound (2C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methyl group, m is 4, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX129).

[0956] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 It is a fluorine atom, m is 4, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX130).

[0957] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 It is a chlorine atom, m is 4, R X3 R X4 R X5 R X6 and R X7The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX131).

[0958] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 It is a fluorine atom, m is 4, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX132).

[0959] In compound (2C), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 It is a chlorine atom, m is 4, R X3 R X4 R X5 R X6 and R X7 It refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX133).

[0960] In the compound represented by formula (3C) (hereinafter referred to as compound (3C)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X28 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX134).

[0961] [Chemical Formula 63]

[0962]

[0963] In compound (3C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX135).

[0964] In compound (3C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX136).

[0965] In compound (3C), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 It is a methoxy group, R6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX137).

[0966] In compound (3C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX138).

[0967] In compound (3C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX139).

[0968] In compound (3C), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX140).

[0969] In compound (3C), X is a nitrogen atom, L is NH, and R... 1 For methyl, R X28 For methyl, R 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX141).

[0970] In compound (3C), X is a nitrogen atom, L is NH, and R... 1 For methyl, R X28 R is a fluorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX142).

[0971] In compound (3C), X is a nitrogen atom, L is NH, and R... 1 For methyl, R X28 R is a chlorine atom. 6 The compound is selected from group Y with any substituents (hereinafter referred to as compound group SX143).

[0972] In the compound represented by formula (1D) (hereinafter referred to as compound (1D)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X2 For methyl, R X3 R X4 R X5 R X6 and R X7This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX144).

[0973] [Chemical Formula 64]

[0974]

[0975] In compound (1D), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 For ethyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX145).

[0976] In compound (1D), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX146).

[0977] In compound (1D), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX147).

[0978] In compound (1D), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methoxy group, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX148).

[0979] In compound (1D), X is CH, L is an oxygen atom, and R... 1 For methyl, R X2 It is cyclopropyl, R X3 R X4 R X5 RX6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX149).

[0980] In compound (1D), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 For methyl, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX150).

[0981] In compound (1D), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX151).

[0982] In compound (1D), X is CH, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX152).

[0983] In compound (1D), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 For methyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX153).

[0984] In compound (1D), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX154).

[0985] In compound (1D), X is CH, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX155).

[0986] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 For methyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX156).

[0987] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 For ethyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX157).

[0988] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX158).

[0989] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX159).

[0990] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 It is a methoxy group, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX160).

[0991] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X2 It is cyclopropyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX161).

[0992] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 For methyl, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX162).

[0993] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX163).

[0994] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a fluorine atom. X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX164).

[0995] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1R is a chlorine atom. X2 For methyl, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX165).

[0996] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7 It refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX166).

[0997] In compound (1D), X is a nitrogen atom, L is an oxygen atom, and R... 1 R is a chlorine atom. X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX167).

[0998] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 For methyl, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX168).

[0999] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 For ethyl, R X3 R X4 R X5 R X6 and R X7 It refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX169).

[1000] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 R is a fluorine atom. X3 R X4 RX5 R X6 and R X7 The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX170).

[1001] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX171).

[1002] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 It is a methoxy group, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX172).

[1003] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X2 It is cyclopropyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX173).

[1004] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 For methyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX174).

[1005] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX175).

[1006] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a fluorine atom. X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX176).

[1007] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 For methyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX177).

[1008] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX178).

[1009] In compound (1D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 R is a chlorine atom. X2 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX179).

[1010] In the compound represented by formula (2D) (hereinafter referred to as compound (2D)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X28 For methyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX180).

[1011] [Chemical Formula 65]

[1012]

[1013] In compound (2D), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX181).

[1014] In compound (2D), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX182).

[1015] In compound (2D), X is CH, L is an oxygen atom, and R... 1 For methyl, R X28 It is a methoxy group, R X3 R X4 R X5 R X6 and R X7 It refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX183).

[1016] In compound (2D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 For methyl, R X3 R X4 R X5 R X6 and R X7 The compound is any combination of compounds recorded in combination B (hereinafter referred to as compound group SX184).

[1017] In compound (2D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7The compound is any combination of compounds described in combination B (hereinafter referred to as compound group SX185).

[1018] In compound (2D), X is a nitrogen atom, L is an oxygen atom, and R... 1 For methyl, R X28 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 It refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX186).

[1019] In compound (2D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X28 For methyl, R X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX187).

[1020] In compound (2D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X28 R is a fluorine atom. X3 R X4 R X5 R X6 and R X7 This refers to any combination of compounds described in combination B (hereinafter referred to as compound group SX188).

[1021] In compound (2D), X is a nitrogen atom, L is NH, and R is nitrogen. 1 For methyl, R X28 R is a chlorine atom. X3 R X4 R X5 R X6 and R X7 It refers to any combination of compounds recorded in combination B (hereinafter referred to as compound group SX189).

[1022] In the compound represented by formula (1E) (hereinafter referred to as compound (1E)), X is CH, L is an oxygen atom, and R is a carbon atom. 1 For methyl, R X2 The structure of G is methyl, and the substituent R corresponding to the structure of G is also shown. X8 R X9 R X10 and R X11 It refers to any combination of compounds recorded in combination C (hereinafter referred to as compound group SX190).

[1023] [Chemical Formula 66]

[1024]

[1025] [In the formula, G represents any one of the formulas G1 to G36.]

[1026] [Chemical Formula 67]

[1027]

[1028] [Chemical Formula 68]

[1029]

[1030] [Chemical Formula 69]

[1031]

[1032] Combination C consists of substituent numbers ZC1 to ZC1459. Substituent numbers ZC1 to ZC1459 refer to the structure of G in compounds (1E) and (2E), and the substituent R corresponding to the structure of G. X8 R X9 R X10 and R X11 The combination of these elements, hereinafter, is denoted as [substituent number; G, R]. X8 ,R X9 ,R X10 ,R X11 For example, the substituent number ZC2 means that G is G1 and R is G1. X8 It is methyl, and R X9 R X10 and R X11 It is a combination of hydrogen atoms.

[1033] Combination C

[1034] [ZC1;G1,H,H,H,H],[ZC2;G1,Me,H,H,H],[ZC3;G1,Et,H,H,H],[ZC4;G1,Pr,H,H,H],[ZC5;G1,i-Pr,H,H,H],[ZC6;G1,t-Bu,H,H,H],[ZC7;G1,OMe,H,H,H],[ZC8;G1,OEt,H,H,H],[ZC9;G1,OPr,H,H,H],[ZC10;G1,Oi-Pr,H,H,H],[ZC11;G1,CF3,H,H,H],[ZC12;G1,CF2H,H,H,H],[ZC13;G1,CFH2,H,H,H],[ZC14;G1,F,H,H,H],[ZC15;G1,Cl,H,H,H],[ZC16;G1,Br,H,H,H],[ZC17;G1,CN,H,H,H],[ZC18;G1,Ph,H,H,H],[ZC19;G1,OPh,H,H,H],[ZC20;G1,c-Pr,H,H,H],[ZC21;G1,H,Me,H,H],[ZC22;G1,H,Et,H,H],[ZC23;G1,H,Pr,H,H],[ZC24;G1,H,i-Pr,H,H],[ZC25;G1,H,t-Bu,H,H],[ZC26;G1,H,OMe,H,H],[ZC27;G1,H,OEt,H,H],[ZC28;G1,H,OPr,H,H],[ZC29;G1,H,Oi-Pr,H,H],[ZC30;G1,H,CF3,H,H],[ZC31;G1,H,CF2H,H,H],[ZC32;G1,H,CFH2,H,H],[ZC33;G1,H,F,H,H],[ZC34;G1,H,Cl,H,H],[ZC35;G1,H,Br,H,H],[ZC36;G1,H,CN,H,H],[ZC37;G1,H,Ph,H,H],[ZC38;G1,H,OPh,H,H],[ZC39;G1,H,c-Pr,H,H],[ZC40;G1,H,H,Me,H],[ZC41;G1,H,H,Et,H],[ZC42;G1,H,H,Pr,H],[ZC43;G1,H,H,i-Pr,H],[ZC44;G1,H,H,t-Bu,H],[ZC45;G1,H,H,OMe,H],[ZC46;G1,H,H,OEt,H],[ZC47;G1,H,H,OPr,H],[ZC48;G1,H,H,Oi-Pr,H],[ZC49;G1,H,H,CF3,H],[ZC50;G1,H,H,CF2H,H],[ZC51;G1,H,H,CFH2,H],[ZC52;G1,H,H,F,H],[ZC53;G1,H,H,Cl,H],[ZC54;G1,H,H,Br,H],[ZC55;G1,H,H,CN,H],[ZC56;G1,H,H,Ph,H],[ZC57;G1,H,H,OPh,H],[ZC58;G1,H,H,c-Pr,H],[ZC59;G1,H,H,H,Me],[ZC60;G1,H,H,H,Et],[ZC61;G1,H,H,H,Pr],[ZC62;G1,H,H,H,i-Pr],[ZC63;G1,H,H,H,t-Bu],[ZC64;G1,H,H,H,OMe],[ZC65;G1,H,H,H,OEt],[ZC66;G1,H,H,H,OPr],[ZC67;G1,H,H,H,Oi-Pr],[ZC68;G1,H,H,H,CF3],[ZC69;G1,H,H,H,CF2H],[ZC70;G1,H,H,H,CFH2],[ZC71;G1,H,H,H,F],[ZC72;G1,H,H,H,Cl],[ZC73;G1,H,H,H,Br],[ZC74;G1,H,H,H,CN],[ZC75;G1,H,H,H,Ph],[ZC76;G1,H,H,H,OPh],[ZC77;G1,H,H,H,c-Pr],[ZC78;G1,F,F,H,H],[ZC79;G1,F,H,F,H],[ZC80;G1,F,H,H,F],[ZC81;G1,H,F,F,H],[ZC82;G1,H,F,H,F],[ZC83;G1,H,H,F,F],[ZC84;G1,Cl,Cl,H,H],[ZC85;G1,Cl,H,Cl,H],[ZC86;G1,Cl,H,H,Cl],[ZC87;G1,H,Cl,Cl,H],[ZC88;G1,H,Cl,H,Cl],[ZC89;G1,H,H,Cl,Cl],[ZC90;G2,H,H,H,H],[ZC91;G2,Me,H,H,H],[ZC92;G2,Et,H,H,H],[ZC93;G2,Pr,H,H,H],[ZC94;G2,i-Pr,H,H,H],[ZC95;G2,t-Bu,H,H,H],[ZC96;G2,OMe,H,H,H],[ZC97;G2,OEt,H,H,H],[ZC98;G2,OPr,H,H,H],[ZC99;G2,Oi-Pr,H,H,H],[ZC100;G2,CF3,H,H,H],;

[1035] [ZC101;G2,CF2H,H,H,H],[ZC102;G2,CFH2,H,H,H],[ZC103;G2,F,H,H,H],[ZC104;G2,Cl,H,H,H],[ZC105;G2,Br,H,H,H],[ZC106;G2,CN,H,H,H],[ZC107;G2,Ph,H,H,H],[ZC108;G2,OPh,H,H,H],[ZC109;G2,c-Pr,H,H,H],[ZC110;G2,H,Me,H,H],[ZC111;G2,H,Et,H,H],[ZC112;G2,H,Pr,H,H],[ZC113;G2,H,i-Pr,H,H],[ZC114;G2,H,t-Bu,H,H],[ZC115;G2,H,OMe,H,H],[ZC116;G2,H,OEt,H,H],[ZC117;G2,H,OPr,H,H],[ZC118;G2,H,Oi-Pr,H,H],[ZC119;G2,H,CF3,H,H],[ZC120;G2,H,CF2H,H,H],[ZC121;G2,H,CFH2,H,H],[ZC122;G2,H,F,H,H],[ZC123;G2,H,Cl,H,H],[ZC124;G2,H,Br,H,H],[ZC125;G2,H,CN,H,H],[ZC126;G2,H,Ph,H,H],[ZC127;G2,H,OPh,H,H],[ZC128;G2,H,c-Pr,H,H],[ZC129;G2,H,H,Me,H],[ZC130;G2,H,H,Et,H],[ZC131;G2,H,H,Pr,H],[ZC132;G2,H,H,i-Pr,H],[ZC133;G2,H,H,t-Bu,H],[ZC134;G2,H,H,OMe,H],[ZC135;G2,H,H,OEt,H],[ZC136;G2,H,H,OPr,H],[ZC137;G2,H,H,Oi-Pr,H],[ZC138;G2,H,H,CF3,H],[ZC139;G2,H,H,CF2H,H],[ZC140;G2,H,H,CFH2,H],[ZC141;G2,H,H,F,H],[ZC142;G2,H,H,Cl,H],[ZC143;G2,H,H,Br,H],[ZC144;G2,H,H,CN,H],[ZC145;G2,H,H,Ph,H],[ZC146;G2,H,H,OPh,H],[ZC147;G2,H,H,c-Pr,H],[ZC148;G2,H,H,H,Me],[ZC149;G2,H,H,H,Et],[ZC150;G2,H,H,H,Pr],[ZC151;G2,H,H,H,i-Pr],[ZC152;G2,H,H,H,t-Bu],[ZC153;G2,H,H,H,OMe],[ZC154;G2,H,H,H,OEt],[ZC155;G2,H,H,H,OPr],[ZC156;G2,H,H,H,Oi-Pr],[ZC157;G2,H,H,H,CF3],[ZC158;G2,H,H,H,CF2H],[ZC159;G2,H,H,H,CFH2],[ZC160;G2,H,H,H,F],[ZC161;G2,H,H,H,Cl],[ZC162;G2,H,H,H,Br],[ZC163;G2,H,H,H,CN],[ZC164;G2,H,H,H,Ph],[ZC165;G2,H,H,H,OPh],[ZC166;G2,H,H,H,c-Pr],[ZC167;G2,F,F,H,H],[ZC168;G2,F,H,F,H],[ZC169;G2,F,H,H,F],[ZC170;G2,H,F,F,H],[ZC171;G2,H,F,H,F],[ZC172;G2,H,H,F,F],[ZC173;G2,Cl,Cl,H,H],[ZC174;G2,Cl,H,Cl,H],[ZC175;G2,Cl,H,H,Cl],[ZC176;G2,H,Cl,Cl,H],[ZC177;G2,H,Cl,H,Cl],[ZC178;G2,H,H,Cl,Cl],[ZC179;G3,H,H,H,H],[ZC180;G3,Me,H,H,H],[ZC181;G3,Et,H,H,H],[ZC182;G3,Pr,H,H,H],[ZC183;G3,i-Pr,H,H,H],[ZC184;G3,t-Bu,H,H,H],[ZC185;G3,OMe,H,H,H],[ZC186;G3,OEt,H,H,H],[ZC187;G3,OPr,H,H,H],[ZC188;G3,Oi-Pr,H,H,H],[ZC189;G3,CF3,H,H,H],[ZC190;G3,CF2H,H,H,H],[ZC191;G3,CFH2,H,H,H],[ZC192;G3,F,H,H,H],[ZC193;G3,Cl,H,H,H],[ZC194;G3,Br,H,H,H],[ZC195;G3,CN,H,H,H],[ZC196;G3,Ph,H,H,H],[ZC197;G3,OPh,H,H,H],[ZC198;G3,c-Pr,H,H,H],[ZC199;G3,H,Me,H,H],[ZC200;G3,H,Et,H,H],;

[1036] [ZC201;G3,H,Pr,H,H],[ZC202;G3,H,i-Pr,H,H],[ZC203;G3,H,t-Bu,H,H],[ZC204;G3,H,OMe,H,H],[ZC205;G3,H,OEt,H,H],[ZC206;G3,H,OPr,H,H],[ZC207;G3,H,Oi-Pr,H,H],[ZC208;G3,H,CF3,H,H],[ZC209;G3,H,CF2H,H,H],[ZC210;G3,H,CFH2,H,H],[ZC211;G3,H,F,H,H],[ZC212;G3,H,Cl ,H,H],[ZC213;G3,H,Br,H,H],[ZC214;G3,H,CN,H,H],[ZC215;G3,H,Ph,H,H],[ZC216;G3,H,OPh,H,H],[ZC217;G3,H,c-Pr,H,H],[ZC218;G3,H,H,Me,H],[ZC219;G3,H,H,Et,H],[ZC220;G3,H,H,Pr,H],[ZC221;G3,H,H,i-Pr,H],[ZC222;G3,H,H,t-Bu,H],[ZC223;G3,H,H,OMe,H],[ZC224;G3,H,H,O Et,H],[ZC225;G3,H,H,OPr,H],[ZC226;G3,H,H,Oi-Pr,H],[ZC227;G3,H,H,CF3,H],[ZC228;G3,H,H,CF2H,H],[ZC229;G3,H,H,CFH2,H],[ZC230;G3,H,H,F,H],[ZC231;G3,H,H,Cl,H],[ZC232;G3,H,H,Br,H],[ZC233;G3,H,H,CN,H],[ZC234;G3,H,H,Ph,H],[ZC235;G3,H,H,OPh,H],[ZC236;G3,H,H ,c-Pr,H],[ZC237;G3,H,H,H,Me],[ZC238;G3,H,H,H,Et],[ZC239;G3,H,H,H,Pr],[ZC240;G3,H,H,H,i-Pr],[ZC241;G3,H,H,H,t-Bu],[ZC242;G3,H,H,H,OMe],[ZC243;G3,H,H,H,OEt],[ZC244;G3,H,H,H,OPr],[ZC245;G3,H,H,H,Oi-Pr],[ZC246;G3,H,H,H,CF3],[ZC247;G3,H,H,H,CF2H],[ZC248;G3,H,H,H,CFH2],[ZC249;G3,H,H,H,F],[ZC250;G3,H,H,H,Cl],[ZC251;G3,H,H,H,Br],[ZC252;G3,H,H,H,CN],[ZC253;G3,H,H,H,Ph],[ZC254;G3,H,H,H,OPh],[ZC255;G3,H,H,H,c-Pr],[ZC256;G3,F,F,H,H],[ZC257;G3,F,H,F,H],[ZC258;G3,F,H,H,F],[ZC259;G3,H,F,F,H],[ZC260;G3,H,F,H,F],[ZC261;G3,H,H,F,F],[ZC262;G3,Cl,Cl,H,H],[ZC263;G3,Cl,H,Cl,H],[ZC264;G3,Cl,H,H,Cl],[ZC265;G3,H,Cl,Cl,H],[ZC266;G3,H,Cl,H,Cl],[ZC267;G3,H,H,Cl,Cl],[ZC268;G4,H,H,H,-],[ZC269;G4,Me,H,H,-],[ZC270;G4,Et,H,H,-],[ZC271;G4,Pr,H,H,-],[ZC272;G4,i-Pr,H,H,-],[ZC273;G4,OMe,H,H,-],[ZC274;G4,CF3,H,H,-],[ZC275;G4,F,H,H,-],[ZC276;G4,Cl,H,H,-],[ZC277;G4,Br,H,H,-],[ZC278;G4,CN,H,H,-],[ZC279;G4,Ph,H,H,-],[ZC280;G4,OPh,H,H,-],[ZC281;G4,c-Pr,H,H,-],[ZC282;G4,H,Me,H,-],[ZC283;G4,H,Et,H,-],[ZC284;G4,H,Pr,H,-],[ZC285;G4,H,i-Pr,H,-],[ZC286;G4,H,OMe,H,-],[ZC287;G4,H,CF3,H,-],[ZC288;G4,H,F,H,-],[ZC289;G4,H,Cl,H,-],[ZC290;G4,H,Br,H,-],[ZC291;G4,H,CN,H,-],[ZC292;G4,H,Ph,H,-],[ZC293;G4,H,OPh,H,-],[ZC294;G4,H,c-Pr,H,-],[ZC295;G4,H,H,Me,-],[ZC296;G4,H,H,Et,-],[ZC297;G4,H,H,Pr,-],[ZC298;G4,H,H,i-Pr,-],[ZC299;G4,H,H,OMe,-],[ZC300;G4,H,H,CF3,-],;

[1037] [ZC301;G4,H,H,F,-],[ZC302;G4,H,H,Cl,-],[ZC303;G4,H,H,Br,-],[ZC304;G4,H,H,CN,-],[ZC305;G4,H,H,Ph,-],[ZC306;G4,H,H,OPh,-],[ZC307;G4,H,H,c-Pr,-],[ZC308;G5,H,H,H,-],[ZC309;G5,Me,H,H,-],[ZC310;G5,Et,H,H,-],[ZC311;G5,Pr,H,H,-],[ZC312;G5,i-Pr,H,H,-],[ZC313;G5,OMe,H,H,-],[ZC314;G5,CF3,H,H,-],[ZC315;G5,F,H,H,-],[ZC316;G5,Cl,H,H,-],[ZC317;G5,Br,H,H,-],[ZC318;G5,CN,H,H,-],[ZC319;G5,c-Pr,H,H,-],[ZC320;G5,H,Me,H,-],[ZC321;G5,H,Et,H,-],[ZC322;G5,H,Pr,H,-],[ZC323;G5,H,i-Pr,H,-],[ZC324;G5,H,OMe,H,-],[ZC325;G5,H,CF3,H,-],[ZC326;G5,H,F,H,-],[ZC327;G5,H,Cl,H,-],[ZC328;G5,H,Br,H,-],[ZC329;G5,H,CN,H,-],[ZC330;G5,H,Ph,H,-],[ZC331;G5,H,OPh,H,-],[ZC332;G5,H,c-Pr,H,-],[ZC333;G5,H,H,Me,-],[ZC334;G5,H,H,Et,-],[ZC335;G5,H,H,Pr,-],[ZC336;G5,H,H,i-Pr,-],[ZC337;G5,H,H,OMe,-],[ZC338;G5,H,H,CF3,-],[ZC339;G5,H,H,F,-],[ZC340;G5,H,H,Cl,-],[ZC341;G5,H,H,Br,-],[ZC342;G5,H,H,CN,-],[ZC343;G5,H,H,c-Pr,-],[ZC344;G6,H,H,H,-],[ZC345;G6,Me,H,H,-],[ZC346;G6,Et,H,H,-],[ZC347;G6,Pr,H,H,-],[ZC348;G6,i-Pr,H,H,-],[ZC349;G6,OMe,H,H,-],[ZC350;G6,CF3,H,H,-],[ZC351;G6,F,H,H,-],[ZC352;G6,Cl,H,H,-],[ZC353;G6,Br,H,H,-],[ZC354;G6,CN,H,H,-],[ZC355;G6,Ph,H,H,-],[ZC356;G6,OPh,H,H,-],[ZC357;G6,c-Pr,H,H,-],[ZC358;G6,H,Me,H,-],[ZC359;G6,H,Et,H,-],[ZC360;G6,H,Pr,H,-],[ZC361;G6,H,i-Pr,H,-],[ZC362;G6,H,OMe,H,-],[ZC363;G6,H,CF3,H,-],[ZC364;G6,H,F,H,-],[ZC365;G6,H,Cl,H,-],[ZC366;G6,H,Br,H,-],[ZC367;G6,H,CN,H,-],[ZC368;G6,H,Ph,H,-],[ZC369;G6,H,OPh,H,-],[ZC370;G6,H,c-Pr,H,-],[ZC371;G6,H,H,Me,-],[ZC372;G6,H,H,Et,-],[ZC373;G6,H,H,Pr,-],[ZC374;G6,H,H,i-Pr,-],[ZC375;G6,H,H,OMe,-],[ZC376;G6,H,H,CF3,-],[ZC377;G6,H,H,F,-],[ZC378;G6,H,H,Cl,-],[ZC379;G6,H,H,Br,-],[ZC380;G6,H,H,CN,-],[ZC381;G6,H,H,c-Pr,-],[ZC382;G7,H,H,H,-],[ZC383;G7,Me,H,H,-],[ZC384;G7,Et,H,H,-],[ZC385;G7,Pr,H,H,-],[ZC386;G7,i-Pr,H,H,-],[ZC387;G7,OMe,H,H,-],[ZC388;G7,CF3,H,H,-],[ZC389;G7,F,H,H,-],[ZC390;G7,Cl,H,H,-],[ZC391;G7,Br,H,H,-],[ZC392;G7,CN,H,H,-],[ZC393;G7,Ph,H,H,-],[ZC394;G7,OPh,H,H,-],[ZC395;G7,c-Pr,H,H,-],[ZC396;G7,H,Me,H,-],[ZC397;G7,H,Et,H,-],[ZC398;G7,H,Pr,H,-],[ZC399;G7,H,i-Pr,H,-],[ZC400;G7,H,OMe,H,-],;

[1038] [ZC401;G7,H,CF3,H,-],[ZC402;G7,H,F,H,-],[ZC403;G7,H,Cl,H,-],[ZC404;G7,H,Br,H,-],[ZC405;G7,H,CN,H,-],[ZC406;G7,H,Ph,H,-],[ZC407;G7,H,OPh,H,-],[ZC408;G7,H,c-Pr,H,-],[ZC409;G7,H,H,Me,-],[ZC410;G7,H,H,Et,-],[ZC411;G7,H,H,Pr,-],[ZC412;G7,H,H,i-Pr,-],[ ZC413;G7,H,H,OMe,-],[ZC414;G7,H,H,CF3,-],[ZC415;G7,H,H,F,-],[ZC416;G7,H,H,Cl,-],[ZC417;G7,H,H,Br,-],[ZC418;G7,H,H,CN,-],[ZC419;G7,H,H,c-Pr,-],[ZC420;G8,H,H,H,-],[ZC421;G8,Me,H,H,-],[ZC422;G8,Et,H,H,-],[ZC423;G8,Pr,H,H,-],[ZC424;G8,i-Pr,H,H,-],[ZC4 25. ;G8,c-Pr,H,H,-],[ZC432;G8,H,Me,H,-],[ZC433;G8,H,Et,H,-],[ZC434;G8,H,Pr,H,-],[ZC435;G8,H,i-Pr,H,-],[ZC436;G8,H,OMe,H,-],[ZC43 7;G8,H,CF3,H,-],[ZC438;G8,H,F,H,-],[ZC439;G8,H,Cl,H,-],[ZC440;G8,H,Br,H,-],[ZC441;G8,H,CN,H,-],[ZC442;G8,H,Ph,H,-],[ZC443;G 8,H,OPh,H,-],[ZC444;G8,H,c-Pr,H,-],[ZC445;G8,H,H,Me,-],[ZC446;G8,H,H,Et,-],[ZC447;G8,H,H,Pr,-],[ZC448;G8,H,H,i-Pr,-],[ZC449;G8,H,H,OMe,-],[ZC450;G8,H,H,CF3,-],[ZC451;G8,H,H,F,-],[ZC452;G8,H,H,Cl,-],[ZC453;G8,H,H,Br,-],[ZC454;G8,H,H,CN,-],[ZC455;G8,H,H,c-Pr,-],[ZC456;G9,H,H,H,-],[ZC457;G9,Me,H,H,-],[ZC458;G9,Et,H,H,-],[ZC459;G9,Pr,H,H,-],[ZC460;G9,i-Pr,H,H,-],[ZC461;G9,OMe,H,H,-],[ZC462;G9,CF3,H,H,-],[ZC463;G9,F,H,H,-],[ZC464;G9,Cl,H,H,-],[ZC465;G9,Br,H,H,-],[ZC466;G9,CN,H,H,-],[ZC467;G9,Ph,H,H,-],[ZC468;G9,OPh,H,H,-],[ZC469;G9,c-Pr,H,H,-],[ZC470;G9,H,Me,H,-],[ZC471;G9,H,Et,H,-],[ZC472;G9,H,Pr,H,-],[ZC473;G9,H,i-Pr,H,-],[ZC474;G9,H,OMe,H,-],[ZC475;G9,H,CF3,H,-],[ZC476;G9,H,F,H,-],[ZC477;G9,H,Cl,H,-],[ZC478;G9,H,Br,H,-],[ZC479;G9,H,CN,H,-],[ZC480;G9,H,Ph,H,-],[ZC481;G9,H,OPh,H,-],[ZC482;G9,H,c-Pr,H,-],[ZC483;G9,H,H,Me,-],[ZC484;G9,H,H,Et,-],[ZC485;G9,H,H,Pr,-],[ZC486;G9,H,H,i-Pr,-],[ZC487;G9,H,H,OMe,-],[ZC488;G9,H,H,CF3,-],[ZC489;G9,H,H,F,-],[ZC490;G9,H,H,Cl,-],[ZC491;G9,H,H,Br,-],[ZC492;G9,H,H,CN,-],[ZC493;G9,H,H,c-Pr,-],[ZC494;G10,H,H,H,-],[ZC495;G10,Me,H,H,-],[ZC496;G10,Et,H,H,-],[ZC497;G10,Pr,H,H,-],[ZC498;G10,i-Pr,H,H,-],[ZC499;G10,OMe,H,H,-],[ZC500;G10,CF3,H,H,-],;

[1039] [ZC501;G10,F,H,H,-],[ZC502;G10,Cl,H,H,-],[ZC503;G10,Br,H,H,-],[ZC504;G10,CN,H,H,-],[ZC505;G10,Ph,H,H,-],[ZC506;G10,OPh,H,H,-],[ZC507;G10,c-Pr,H,H,-],[ZC508;G10,H,Me,H,-],[ZC509;G10,H,Et,H,-],[ZC510;G10,H,Pr,H,-],[ZC511;G10,H,i-Pr,H,-],[ZC512;G10,H,OMe,H,-],[ZC513;G10,H,CF3,H,-],[ZC514;G10,H,F,H,-],[ZC515;G10,H,Cl,H,-],[ZC516;G10,H,Br,H,-],[ZC517;G10,H,CN,H,-],[ZC518;G10,H,Ph,H,-],[ZC519;G10,H,OPh,H,-],[ZC520;G10,H,c-Pr,H,-],[ZC521;G10,H,H,Me,-],[ZC522;G10,H,H,Et,-],[ZC523;G10,H,H,Pr,-],[ZC524;G10,H,H,i-Pr,-],[ZC525;G10,H,H,OMe,-],[ZC526;G10,H,H,CF3,-],[ZC527;G10,H,H,F,-],[ZC528;G10,H,H,Cl,-],[ZC529;G10,H,H,Br,-],[ZC530;G10,H,H,CN,-],[ZC531;G10,H,H,Ph,-],[ZC532;G10,H,H,OPh,-],[ZC533;G10,H,H,c-Pr,-],[ZC534;G11,H,H,H,-],[ZC535;G11,Me,H,H,-],[ZC536;G11,Et,H,H,-],[ZC537;G11,Pr,H,H,-],[ZC538;G11,i-Pr,H,H,-],[ZC539;G11,OMe,H,H,-],[ZC540;G11,CF3,H,H,-],[ZC541;G11,F,H,H,-],[ZC542;G11,Cl,H,H,-],[ZC543;G11,Br,H,H,-],[ZC544;G11,CN,H,H,-],[ZC545;G11,Ph,H,H,-],[ZC546;G11,OPh,H,H,-],[ZC547;G11,c-Pr,H,H,-],[ZC548;G11,H,Me,H,-],[ZC549;G11,H,Et,H,-],[ZC550;G11,H,Pr,H,-],[ZC551;G11,H,i-Pr,H,-],[ZC552;G11,H,OMe,H,-],[ZC553;G11,H,CF3,H,-],[ZC554;G11,H,F,H,-],[ZC555;G11,H,Cl,H,-],[ZC556;G11,H,Br,H,-],[ZC557;G11,H,CN,H,-],[ZC558;G11,H,Ph,H,-],[ZC559;G11,H,OPh,H,-],[ZC560;G11,H,c-Pr,H,-],[ZC561;G11,H,H,Me,-],[ZC562;G11,H,H,Et,-],[ZC563;G11,H,H,Pr,-],[ZC564;G11,H,H,i-Pr,-],[ZC565;G11,H,H,OMe,-],[ZC566;G11,H,H,CF3,-],[ZC567;G11,H,H,F,-],[ZC568;G11,H,H,Cl,-],[ZC569;G11,H,H,Br,-],[ZC570;G11,H,H,CN,-],[ZC571;G11,H,H,Ph,-],[ZC572;G11,H,H,OPh,-],[ZC573;G11,H,H,c-Pr,-],[ZC574;G12,H,H,H,-],[ZC575;G12,Me,H,H,-],[ZC576;G12,Et,H,H,-],[ZC577;G12,Pr,H,H,-],[ZC578;G12,i-Pr,H,H,-],[ZC579;G12,t-Bu,H,H,-],[ZC580;G12,CF3,H,H,-],[ZC581;G12,CHF2,H,H,-],[ZC582;G12,CH2F,H,H,-],[ZC583;G12,Ph,H,H,-],[ZC584;G12,c-Pr,H,H,-],[ZC585;G12,c-Bu,H,H,-],[ZC586;G12,c-Pen,H,H,-],[ZC587;G12,C-Hex,H,H,-],[ZC588;G12,Me,Me,H,-],[ZC589;G12,Me,Et,H,-],[ZC590;G12,Me,Pr,H,-],[ZC591;G12,Me,i-Pr,H,-],[ZC592;G12,Me,OMe,H,-],[ZC593;G12,Me,CF3,H,-],[ZC594;G12,Me,F,H,-],[ZC595;G12,Me,Cl,H,-],[ZC596;G12,Me,Br,H,-],[ZC597;G12,Me,CN,H,-],[ZC598;G12,Me,c-Pr,H,-],[ZC599;G12,Me,H,Me,-],[ZC600;G12,Me,H,Et,-],;

[1040] [ZC601;G12,Me,H,Pr,-],[ZC602;G12,Me,H,i-Pr,-],[ZC603;G12,Me,H,OMe,-],[ZC604;G12,Me,H,CF3,-],[ZC605;G12,Me,H,F,-],[ZC606;G12,Me,H,Cl,-],[ZC607;G12,Me,H,Br,-],[ZC608;G12,Me,H,CN,-],[ZC609;G12,Me,H,c-Pr,-],[ZC610;G13,H,H,H,-],[ZC611;G13,Me,H,H,-],[ZC612;G13,Et,H,H,-],[ZC613;G13,Pr,H,H,-],[ZC614;G13,i-Pr,H,H,-],[ZC615;G13,t-Bu,H,H,-],[ZC616;G13,OMe,H,H,-],[ZC617;G13,OEt,H,H,-],[ZC618;G13,OPr,H,H,-],[ZC619;G13,Oi-Pr,H,H,-],[ZC620;G13,CF3,H,H,-],[ZC621;G13,CF2H,H,H,-],[ZC622;G13,CFH2,H,H,-],[ZC623;G13,F,H,H,-],[ZC624;G13,Cl,H,H,-],[ZC625;G13,Br,H,H,-],[ZC626;G13,CN,H,H,-],[ZC627;G13,Ph,H,H,-],[ZC628;G13,OPh,H,H,-],[ZC629;G13,c-Pr,H,H,-],[ZC630;G13,H,Me,H,-],[ZC631;G13,H,Et,H,-],[ZC632;G13,H,Pr,H,-],[ZC633;G13,H,i-Pr,H,-],[ZC634;G13,H,t-Bu,H,-],[ZC635;G13,H,OMe,H,-],[ZC636;G13,H,OEt,H,-],[ZC637;G13,H,OPr,H,-],[ZC638;G13,H,Oi-Pr,H,-],[ZC639;G13,H,CF3,H,-],[ZC640;G13,H,CF2H,H,-],[ZC641;G13,H,CFH2,H,-],[ZC642;G13,H,F,H,-],[ZC643;G13,H,Cl,H,-],[ZC644;G13,H,Br,H,-],[ZC645;G13,H,CN,H,-],[ZC646;G13,H,Ph,H,-],[ZC647;G13,H,OPh,H,-],[ZC648;G13,H,c-Pr,H,-],[ZC649;G13,H,H,Me,-],[ZC650;G13,H,H,Et,-],[ZC651;G13,H,H,Pr,-],[ZC652;G13,H,H,i-Pr,-],[ZC653;G13,H,H,t-Bu,-],[ZC654;G13,H,H,OMe,-],[ZC655;G13,H,H,OEt,-],[ZC656;G13,H,H,OPr,-],[ZC657;G13,H,H,Oi-Pr,-],[ZC658;G13,H,H,CF3,-],[ZC659;G13,H,H,CF2H,-],[ZC660;G13,H,H,CFH2,-],[ZC661;G13,H,H,F,-],[ZC662;G13,H,H,Cl,-],[ZC663;G13,H,H,Br,-],[ZC664;G13,H,H,CN,-],[ZC665;G13,H,H,Ph,-],[ZC666;G13,H,H,OPh,-],[ZC667;G13,H,H,c-Pr,-],[ZC668;G13,CH(Me)Et,H,H,-],[ZC669;G13,CH(Et)2,H,H,-],[ZC670;G13,CH2(i-Pr),H,H,-],[ZC671;G13,C(Me)=CH(Me),H,H,-],[ZC672;G13,C(Me)=CH2,H,H,-],[ZC673;G13,CH=CH(Me),H,H,-],[ZC674;G13,CH=CH2,H,H,-],[ZC675;G13,CC(c-Pr),H,H,-],[ZC676;G13,CC(Me),H,H,-],[ZC677;G13,CHF2,H,H,-],[ZC678;G13,CF2Me,H,H,-],[ZC679;G13,CF2CF3,H,H,-],[ZC680;G13,C(CF3)CH2,H,H,-],[ZC681;G13,CF2Cl,H,H,-],[ZC682;G13,CH(Me)CF3,H,H,-],[ZC683;G13,c-Bu,H,H,-],[ZC684;G13,c-Pen,H,H,-],[ZC685;G13,c-Hex,H,H,-],[ZC686;G13,1-Me-(c-Pr),H,H,-],[ZC687;G13,1-F-(c-Pr),H,H,-],[ZC688; G13,2,2-F2-(c-Pr),H,H,-],[ZC689; G13,I,H,H,-],[ZC690; G13,CH2CN,H,H,-],[ZC691; G13,CH2OMe,H,H,-],[ZC692; G13,CH2SMe,H,H,-],[ZC693; G13,c-hexen-1-yl,H,H,-],[ZC694; G13,OCHF2,H,H,-],[ZC695; G13,OCF3,H,H,-],[ZC696; G13,SCF3,H,H,-],[ZC697; G13,C(Me)=NOMe,H,H,-],[ZC698; G13,H,c-Bu,H,-],[ZC699; G13,H,c-Pen,H,-],[ZC700; G13,H,c-Hex,H,-];

[1041] [ZC701;G13,H,CCH,H,-],[ZC702;G13,H,CH2OMe,H,-],[ZC703;G13,H,I,H,-],[ZC704;G13,H,S(i-Pr),H,-],[ZC705;G13,Me,Me,H,-],[ZC706;G13,Pr,Me,H,-],[ZC707;G13,i-Pr,Me,H,-],[ZC708;G13,CHF2,Me,H,-],[ZC709;G13,CF3,Me,H,-],[ZC710;G13,c-Pr,Me,H,-],[ZC711;G13,c-Hex,Me,H,-],[ZC712;G13,OMe,Me,H,-],[ZC713;G13,O(i-Pr),Me,H,-],[ZC714;G13,F,Me,H,-],[ZC715;G13,Cl,Me,H,-],[ZC716;G13,Br,Me,H,-],[ZC717;G13,i-Pr,F,H,-],[ZC718;G13,Me,F,H,-],[ZC719;G13,Pr,F,H,-],[ZC720;G13,CHF2,F,H,-],[ZC721;G13,CF3,F,H,-],[ZC722;G13,c-Pr,F,H,-],[ZC723;G13,c-Hex,F,H,-],[ZC724;G13,OMe,F,H,-],[ZC725;G13,Oi-Pr,F,H,-],[ZC726;G13,F,F,H,-],[ZC727;G13,Cl,F,H,-],[ZC728;G13,Br,F,H,-],[ZC729;G13,Pr,Cl,H,-],[ZC730;G13,i-Pr,Cl,H,-],[ZC731;G13,c-Hex,Cl,H,-],[ZC732;G13,Cl,Cl,H,-],[ZC733;G13,Oi-Pr,Cl,H,-],[ZC734;G13,Me,Cl,H,-],[ZC735;G13,CHF2,Cl,H,-],[ZC736;G13,CF3,Cl,H,-],[ZC737;G13,c-Pr,Cl,H,-],[ZC738;G13,OMe,Cl,H,-],[ZC739;G13,F,Cl,H,-],[ZC740;G13,Br,Cl,H,-],[ZC741;G13,Me,Br,H,-],[ZC742;G13,c-Hex,Br,H,-],[ZC743;G13,Pr,Br,H,-],[ZC744;G13,i-Pr,Br,H,-],[ZC745;G13,CHF2,Br,H,-],[ZC746;G13,CF3,Br,H,-],[ZC747;G13,c-Pr,Br,H,-],[ZC748;G13,OMe,Br,H,-],[ZC749;G13,Oi-Pr,Br,H,-],[ZC750;G13,F,Br,H,-],[ZC751;G13,Cl,Br,H,-],[ZC752;G13,Br,Br,H,-],[ZC753;G14,H,H,H,-],[ZC754;G14,Me,H,H,-],[ZC755;G14,Et,H,H,-],[ZC756;G14,Pr,H,H,-],[ZC757;G14,i-Pr,H,H,-],[ZC758;G14,t-Bu,H,H,-],[ZC759;G14,CF3,H,H,-],[ZC760;G14,CHF2,H,H,-],[ZC761;G14,CH2F,H,H,-],[ZC762;G14,Ph,H,H,-],[ZC763;G14,c-Pr,H,H,-],[ZC764;G14,c-Bu,H,H,-],[ZC765;G14,c-Pen,H,H,-],[ZC766;G14,C-Hex,H,H,-],[ZC767;G14,Me,Me,H,-],[ZC768;G14,Me,Et,H,-],[ZC769;G14,Me,Pr,H,-],[ZC770;G14,Me,i-Pr,H,-],[ZC771;G14,Me,OMe,H,-],[ZC772;G14,Me,CF3,H,-],[ZC773;G14,Me,F,H,-],[ZC774;G14,Me,Cl,H,-],[ZC775;G14,Me,Br,H,-],[ZC776;G14,Me,CN,H,-],[ZC777;G14,Me,c-Pr,H,-],[ZC778;G14,Me,H,Me,-],[ZC779;G14,Me,H,Et,-],[ZC780;G14,Me,H,Pr,-],[ZC781;G14,Me,H,i-Pr,-],[ZC782;G14,Me,H,OMe,-],[ZC783;G14,Me,H,CF3,-],[ZC784;G14,Me,H,F,-],[ZC785;G14,Me,H,Cl,-],[ZC786;G14,Me,H,Br,-],[ZC787;G14,Me,H,CN,-],[ZC788;G14,Me,H,c-Pr,-],[ZC789;G15,H,H,H,-],[ZC790;G15,Me,H,H,-],[ZC791;G15,Et,H,H,-],[ZC792;G15,Pr,H,H,-],[ZC793;G15,i-Pr,H,H,-],[ZC794;G15,OMe,H,H,-],[ZC795;G15,CF3,H,H,-],[ZC796;G15,F,H,H,-],[ZC797;G15,Cl,H,H,-],[ZC798;G15,Br,H,H,-],[ZC799;G15,CN,H,H,-],[ZC800;G15,Ph,H,H,-],;

[1042] [ZC801;G15,OPh,H,H,-],[ZC802;G15,c-Pr,H,H,-],[ZC803;G15,H,Me,H,-],[ZC804;G15,H,Et,H,-],[ZC805;G15,H,Pr,H,-],[ZC806;G15,H,i-Pr,H,-],[ZC807;G15,H,OMe,H,-],[ZC808;G15,H,CF3,H,-],[ZC809;G15,H,F,H,-],[ZC810;G15,H,Cl,H,-],[ZC811;G15,H,Br,H,-],[ZC812;G15,H,CN,H,-],[ZC813;G15,H,Ph,H,-],[ZC814;G15,H,OPh,H,-],[ZC815;G15,H,c-Pr,H,-],[ZC816;G15,H,H,Me,-],[ZC817;G15,H,H,Et,-],[ZC818;G15,H,H,Pr,-],[ZC819;G15,H,H,i-Pr,-],[ZC820;G15,H,H,OMe,-],[ZC821;G15,H,H,CF3,-],[ZC822;G15,H,H,F,-],[ZC823;G15,H,H,Cl,-],[ZC824;G15,H,H,Br,-],[ZC825;G15,H,H,CN,-],[ZC826;G15,H,H,Ph,-],[ZC827;G15,H,H,OPh,-],[ZC828;G15,H,H,c-Pr,-],[ZC829;G16,H,H,H,-],[ZC830;G16,Me,H,H,-],[ZC831;G16,Et,H,H,-],[ZC832;G16,Pr,H,H,-],[ZC833;G16,i-Pr,H,H,-],[ZC834;G16,OMe,H,H,-],[ZC835;G16,CF3,H,H,-],[ZC836;G16,F,H,H,-],[ZC837;G16,Cl,H,H,-],[ZC838;G16,Br,H,H,-],[ZC839;G16,CN,H,H,-],[ZC840;G16,Ph,H,H,-],[ZC841;G16,OPh,H,H,-],[ZC842;G16,c-Pr,H,H,-],[ZC843;G16,H,Me,H,-],[ZC844;G16,H,Et,H,-],[ZC845;G16,H,Pr,H,-],[ZC846;G16,H,i-Pr,H,-],[ZC847;G16,H,OMe,H,-],[ZC848;G16,H,CF3,H,-],[ZC849;G16,H,F,H,-],[ZC850;G16,H,Cl,H,-],[ZC851;G16,H,Br,H,-],[ZC852;G16,H,CN,H,-],[ZC853;G16,H,c-Pr,H,-],[ZC854;G16,H,H,Me,-],[ZC855;G16,H,H,Et,-],[ZC856;G16,H,H,Pr,-],[ZC857;G16,H,H,i-Pr,-],[ZC858;G16,H,H,OMe,-],[ZC859;G16,H,H,CF3,-],[ZC860;G16,H,H,F,-],[ZC861;G16,H,H,Cl,-],[ZC862;G16,H,H,Br,-],[ZC863;G16,H,H,CN,-],[ZC864;G16,H,H,c-Pr,-],[ZC865;G17,H,H,-,-],[ZC866;G17,Me,H,-,-],[ZC867;G17,Et,H,-,-],[ZC868;G17,Pr,H,-,-],[ZC869;G17,i-Pr,H,-,-],[ZC870;G17,OMe,H,-,-],[ZC871;G17,CF3,H,-,-],[ZC872;G17,F,H,-,-],[ZC873;G17,Cl,H,-,-],[ZC874;G17,Br,H,-,-],[ZC875;G17,CN,H,-,-],[ZC876;G17,Ph,H,-,-],[ZC877;G17,CH2Ph,H,-,-],[ZC878;G17,c-Pr,H,-,-],[ZC879;G17,H,Me,-,-],[ZC880;G17,H,Et,-,-],[ZC881;G17,H,Pr,-,-],[ZC882;G17,H,i-Pr,-,-],[ZC883;G17,H,OMe,-,-],[ZC884;G17,H,CF3,-,-],[ZC885;G17,H,F,-,-],[ZC886;G17,H,Cl,-,-],[ZC887;G17,H,Br,-,-],[ZC888;G17,H,CN,-,-],[ZC889;G17,H,c-Pr,-,-],[ZC890;G18,H,H,-,-],[ZC891;G18,Me,H,-,-],[ZC892;G18,Et,H,-,-],[ZC893;G18,Pr,H,-,-],[ZC894;G18,i-Pr,H,-,-],[ZC895;G18,OMe,H,-,-],[ZC896;G18,CF3,H,-,-],[ZC897;G18,F,H,-,-],[ZC898;G18,Cl,H,-,-],[ZC899;G18,Br,H,-,-],[ZC900;G18,CN,H,-,-],;

[1043] [ZC901;G18,Ph,H,-,-],[ZC902;G18,CH2Ph,H,-,-],[ZC903;G18,c-Pr,H,-,-],[ZC904;G18,H,Me,-,-],[ZC905;G18,H,Et,-,-],[ZC906;G18,H,Pr,-,-],[ZC907;G18,H,i-Pr,-,-],[ZC908;G18,H,OMe,-,-],[ZC909;G18,H,CF3,-,-],[ZC910;G18,H,F,-,-],[ZC911;G18,H,Cl,-,-],[ZC912;G18,H,Br,-,-],[ZC913;G18,H,CN,-,-],[ZC914;G18,H,c-Pr,-,-],[ZC915;G19,H,H,-,-],[ZC916;G19,Me,H,-,-],[ZC917;G19,Et,H,-,-],[ZC918;G19,Pr,H,-,-],[ZC919;G19,i-Pr,H,-,-],[ZC920;G19,OMe,H,-,-],[ZC921;G19,CF3,H,-,-],[ZC922;G19,F,H,-,-],[ZC923;G19,Cl,H,-,-],[ZC924;G19,Br,H,-,-],[ZC925;G19,CN,H,-,-],[ZC926;G19,c-Pr,H,-,-],[ZC927;G19,H,Me,-,-],[ZC928;G19,H,Et,-,-],[ZC929;G19,H,Pr,-,-],[ZC930;G19,H,i-Pr,-,-],[ZC931;G19,H,OMe,-,-],[ZC932;G19,H,CF3,-,-],[ZC933;G19,H,F,-,-],[ZC934;G19,H,Cl,-,-],[ZC935;G19,H,Br,-,-],[ZC936;G19,H,CN,-,-],[ZC937;G19,H,c-Pr,-,-],[ZC938;G20,H,H,-,-],[ZC939;G20,Me,H,-,-],[ZC940;G20,Et,H,-,-],[ZC941;G20,Pr,H,-,-],[ZC942;G20,i-Pr,H,-,-],[ZC943;G20,OMe,H,-,-],[ZC944;G20,CF3,H,-,-],[ZC945;G20,F,H,-,-],[ZC946;G20,Cl,H,-,-],[ZC947;G20,Br,H,-,-],[ZC948;G20,CN,H,-,-],[ZC949;G20,Ph,H,-,-],[ZC950;G20,OPh,H,-,-],[ZC951;G20,c-Pr,H,-,-],[ZC952;G20,H,Me,-,-],[ZC953;G20,H,Et,-,-],[ZC954;G20,H,Pr,-,-],[ZC955;G20,H,i-Pr,-,-],[ZC956;G20,H,OMe,-,-],[ZC957;G20,H,CF3,-,-],[ZC958;G20,H,F,-,-],[ZC959;G20,H,Cl,-,-],[ZC960;G20,H,Br,-,-],[ZC961;G20,H,CN,-,-],[ZC962;G20,H,Ph,-,-],[ZC963;G20,H,OPh,-,-],[ZC964;G20,H,c-Pr,-,-],[ZC965;G21,H,H,-,-],[ZC966;G21,Me,H,-,-],[ZC967;G21,Et,H,-,-],[ZC968;G21,Pr,H,-,-],[ZC969;G21,i-Pr,H,-,-],[ZC970;G21,OMe,H,-,-],[ZC971;G21,CF3,H,-,-],[ZC972;G21,F,H,-,-],[ZC973;G21,Cl,H,-,-],[ZC974;G21,Br,H,-,-],[ZC975;G21,CN,H,-,-],[ZC976;G21,Ph,H,-,-],[ZC977;G21,OPh,H,-,-],[ZC978;G21,c-Pr,H,-,-],[ZC979;G21,H,Me,-,-],[ZC980;G21,H,Et,-,-],[ZC981;G21,H,Pr,-,-],[ZC982;G21,H,i-Pr,-,-],[ZC983;G21,H,OMe,-,-],[ZC984;G21,H,CF3,-,-],[ZC985;G21,H,F,-,-],[ZC986;G21,H,Cl,-,-],[ZC987;G21,H,Br,-,-],[ZC988;G21,H,CN,-,-],[ZC989;G21,H,c-Pr,-,-],[ZC990;G22,H,H,-,-],[ZC991;G22,Me,H,-,-],[ZC992;G22,Et,H,-,-],[ZC993;G22,Pr,H,-,-],[ZC994;G22,i-Pr,H,-,-],[ZC995;G22,OMe,H,-,-],[ZC996;G22,CF3,H,-,-],[ZC997;G22,F,H,-,-],[ZC998;G22,Cl,H,-,-],[ZC999;G22,Br,H,-,-],[ZC1000;G22,CN,H,-,-],;

[1044] [ZC1001; G22, c-Pr, H, -, -], [ZC1002; G22, H, Me, -, -], [ZC1003; G22, H, Et, -, -], [ZC1004; G22, H, Pr, -, -], [ZC1005; G22, H, i-Pr, -, -], [ZC1006; G22, H, OMe, -, -], [ZC1007; G22, H, CF3, -, -], [ZC1008; G22, H, F, -, -], [ZC1009; G22, H, Cl, -, -], [ZC1010; G22, H, Br, -, -], [ZC1011; G22, H, CN, -, -], [ZC1012; G22, H, Ph, -, -], [ZC1013; G22, H, OPh, -, -], [ZC1014; G22, H, c-Pr, -, -], [ZC1015; G23, H, H, -, -], [ZC1016; G23, Me, H, -, -], [ZC1017; G23, Et, H, -, -], [ZC1018; G23, Pr, H, -, -], [ZC1019; G23, i-Pr, H, -, -], [ZC1020; G23, Bu, H, -, -], [ZC1021; G23, t-Bu, H, -, -], [ZC1022; G23, CH2(i-Pr), H, -, -], [ZC1023; G23, OMe, H, -, -], [ZC1024; G23, CF3, H, -, -], [ZC1025; G23, F, H, -, -], [ZC1026; G23, Cl, H, -, -], [ZC1027; G23, Br, H, -, -], [ZC1028; G23, CN, H, -, -], [ZC1029; G23, Ph, H, -, -], [ZC1030; G23, OPh, H, -, -], [ZC1031; G23, c-Pr, H, -, -], [ZC1032; G23, c-Bu, H, -, -], [ZC1033; G23, c-Pen, H, -, -], [ZC1034; G23, c-Hex, H, -, -], [ZC1035; G23, c-hexen-1-yl, H, -, -], [ZC1036; G23, CHF2, H, -, -], [ZC1037; G23, CF2CF3, H, -, -], [ZC1038; G23, CH=CH2, H, -, -], [ZC1039; G23, C(Me)=CH2, H, -, -], [ZC1040; G23, CCH, H, -, -], [ZC1041; G23, CC(c-Pr), H, -, -], [ZC1042; G23, CC(i-Pr), H, -, -], [ZC1043;G23, CC(Me), H, -, -], [ZC1044; G23, CH=NOMe, H, -, -], [ZC1045; G23, C(Me)=NOMe, H, -, -], [ZC1046; G23, CH2O(i-Pr), H, -, -], [ZC1047; G23, CH2OEt, H, -, -], [ZC1048; G23, CH2OPh, H, -, -], [ZC1049; G23, H, Me, -, -], [ZC1050; G23, H, Et, -, -], [ZC1051; G23, H, Pr, -, -], [ZC1052; G23, H, i-Pr, -, -], [ZC1053; G23, H, Bu, -, -], [ZC1054; G23, H, t-Bu, -, -], [ZC1055; G23, H, CH2(i-Pr), -, -], [ZC1056; G23, H, OMe, -, -], [ZC1057; G23, H, CF3, -, -], [ZC1058; G23, H, F, -, -], [ZC1059; G23, H, Cl, -, -], [ZC1060; G23, H, Br, -, -], [ZC1061; G23, H, CN, -, -], [ZC1062; G23, H, Ph, -, -], [ZC1063; G23, H, OPh, -, -], [ZC1064; G23, H, c-Pr, -, -], [ZC1065; G23, H, c-Bu, -, -], [ZC1066; G23, H, c-Pen, -, -], [ZC1067; G23, H, c-Hex, -, -], [ZC1068; G23, H, c-hexen-1-yl, -, -], [ZC1069; G23, H, CHF2, -, -], [ZC1070; G23, H, CF2CF3, -, -], [ZC1071; G23, H, CH=CH2, -, -], [ZC1072; G23, H, C(Me)=CH2, -, -], [ZC1073; G23, H, CCH, -, -], [ZC1074; G23, H, CC(c-Pr), -, -], [ZC1075; G23, H, CC(i-Pr), -, -], [ZC1076; G23, H, CC(Me), -, -], [ZC1077; G23, H, CH=NOMe, -, -], [ZC1078; G23, H, C(Me)=NOMe, -, -], [ZC1079; G23, H, CH2O(i-Pr), -, -], [ZC1080; G23, H, CH2OEt, -, -], [ZC1081; G23, H, CH2OPh, -, -], [ZC1082;G23,Me,Me,-,-],[ZC1083;G23,Me,Et,-,-],[ZC1084;G23,Me,i-Pr,-,-],[ZC1085;G23,Me,c-Pr,-,-],[ZC1086;G23,Me,c-Hex,-,-],[ZC1087;G23,Me,CHF2,-,-],[ZC1088;G23,Me,CF3,-,-],[ZC1089;G23,Me,F,-,-],[ZC1090;G23,Me,Cl,-,-],[ZC1091;G23,Me,Br,-,-],[ZC1092;G23,Cl,Me,-,-],[ZC1093;G23,Cl,Et,-,-],[ZC1094;G23,Cl,i-Pr,-,-],[ZC1095;G23,Cl,c-Pr,-,-],[ZC1096;G23,Cl,c-Hex,-,-],[ZC1097;G23,Cl,CHF2,-,-],[ZC1098;G23,Cl,CF3,-,-],[ZC1099;G23,Cl,F,-,-],[ZC1100;G23,Cl,Cl,-,-],;

[1045] [ZC1101;G23,Cl,Br,-,-],[ZC1102;G23,F,Me,-,-],[ZC1103;G23,F,Et,-,-],[ZC1104;G23,F,i-Pr,-,-],[ZC1105;G23,F,c-Pr,-,-],[ZC1106;G23,F,c-Hex,-,-],[ZC1107;G23,F,CHF2,-,-],[ZC1108;G23,F,CF3,-,-],[ZC1109;G23,F,F,-,-],[ZC1110;G23,F,Cl,-,-],[ZC1111;G23,F,Br,-,-],[ZC1112;G24,H,H,-,-],[ZC1113;G24,Me,H,-,-],[ZC1114;G24,Et,H,-,-],[ZC1115;G24,Pr,H,-,-],[ZC1116;G24,i-Pr,H,-,-],[ZC1117;G24,OMe,H,-,-],[ZC1118;G24,CF3,H,-,-],[ZC1119;G24,F,H,-,-],[ZC1120;G24,Cl,H,-,-],[ZC1121;G24,Br,H,-,-],[ZC1122;G24,CN,H,-,-],[ZC1123;G24,Ph,H,-,-],[ZC1124;G24,OPh,H,-,-],[ZC1125;G24,c-Pr,H,-,-],[ZC1126;G24,H,Me,-,-],[ZC1127;G24,H,Et,-,-],[ZC1128;G24,H,Pr,-,-],[ZC1129;G24,H,i-Pr,-,-],[ZC1130;G24,H,OMe,-,-],[ZC1131;G24,H,CF3,-,-],[ZC1132;G24,H,F,-,-],[ZC1133;G24,H,Cl,-,-],[ZC1134;G24,H,Br,-,-],[ZC1135;G24,H,CN,-,-],[ZC1136;G24,H,c-Pr,-,-],[ZC1137;G25,H,H,H,-],[ZC1138;G25,Me,H,H,-],[ZC1139;G25,Et,H,H,-],[ZC1140;G25,Pr,H,H,-],[ZC1141;G25,i-Pr,H,H,-],[ZC1142;G25,OMe,H,H,-],[ZC1143;G25,CF3,H,H,-],[ZC1144;G25,F,H,H,-],[ZC1145;G25,Cl,H,H,-],[ZC1146;G25,Br,H,H,-],[ZC1147;G25,CN,H,H,-],[ZC1148;G25,Ph,H,H,-],[ZC1149;G25,OPh,H,H,-],[ZC1150;G25,c-Pr,H,H,-],[ZC1151;G25,H,Me,H,-],[ZC1152;G25,H,Et,H,-],[ZC1153;G25,H,Pr,H,-],[ZC1154;G25,H,i-Pr,H,-],[ZC1155;G25,H,OMe,H,-],[ZC1156;G25,H,CF3,H,-],[ZC1157;G25,H,F,H,-],[ZC1158;G25,H,Cl,H,-],[ZC1159;G25,H,Br,H,-],[ZC1160;G25,H,CN,H,-],[ZC1161;G25,H,Ph,H,-],[ZC1162;G25,H,OPh,H,-],[ZC1163;G25,H,c-Pr,H,-],[ZC1164;G25,H,H,Me,-],[ZC1165;G25,H,H,Et,-],[ZC1166;G25,H,H,Pr,-],[ZC1167;G25,H,H,i-Pr,-],[ZC1168;G25,H,H,OMe,-],[ZC1169;G25,H,H,CF3,-],[ZC1170;G25,H,H,F,-],[ZC1171;G25,H,H,Cl,-],[ZC1172;G25,H,H,Br,-],[ZC1173;G25,H,H,CN,-],[ZC1174;G25,H,H,c-Pr,-],[ZC1175;G26,H,H,-,-],[ZC1176;G26,Me,H,-,-],[ZC1177;G26,Et,H,-,-],[ZC1178;G26,Pr,H,-,-],[ZC1179;G26,i-Pr,H,-,-],[ZC1180;G26,OMe,H,-,-],[ZC1181;G26,CF3,H,-,-],[ZC1182;G26,F,H,-,-],[ZC1183;G26,Cl,H,-,-],[ZC1184;G26,Br,H,-,-],[ZC1185;G26,CN,H,-,-],[ZC1186;G26,c-Pr,H,-,-],[ZC1187;G26,H,Me,-,-],[ZC1188;G26,H,Et,-,-],[ZC1189;G26,H,Pr,-,-],[ZC1190;G26,H,i-Pr,-,-],[ZC1191;G26,H,OMe,-,-],[ZC1 192;G26,H,CF3,-,-],[ZC1193;G26,H,F,-,-],[ZC1194;G26,H,Cl,-,-],[ZC1 195;G26,H,Br,-,-],[ZC1196;G26,H,CN,-,-],[ZC1197;G26,H,Ph,-,-],[ZC 1198;G26,H,OPh,-,-],[ZC1199;G26,H,c-Pr,-,-],[ZC1200;G27,H,H,H,-],;

[1046] [ZC1201;G27,Me,H,H,-],[ZC1202;G27,Et,H,H,-],[ZC1203;G27,Pr,H,H,-],[ZC1204;G27,i-Pr,H,H,-],[ZC1205;G27,CF3,H,H,-],[ZC1206;G27,c-Pr,H,H,-],[ZC1207;G27,Me,Me,H,-],[ZC1208;G27,Me,Et,H,-],[ZC1209;G27,Me,Pr,H,-],[ZC1210;G27,Me,i-Pr,H,-],[ZC1211;G27,Me,OMe,H,-],[ZC1212;G27,Me,CF3,H,-],[ZC1213;G27,Me,F,H,-],[ZC1214;G27,Me,Cl,H,-],[ZC1215;G27,Me,CN,H,-],[ZC1216;G27,Me,Ph,H,-],[ZC1217;G27,Me,c-Pr,H,-],[ZC1218;G27,Me,H,Me,-],[ZC1219;G27,Me,H,Et,-],[ZC1220;G27,Me,H,Pr,-],[ZC1221;G27,Me,H,i-Pr,-],[ZC1222;G27,Me,H,OMe,-],[ZC1223;G27,Me,H,CF3,-],[ZC1224;G27,Me,H,F,-],[ZC1225;G27,Me,H,Cl,-],[ZC1226;G27,Me,H,CN,-],[ZC1227;G27,Me,H,Ph,-],[ZC1228;G27,Me,H,c-Pr,-],[ZC1229;G28,H,H,H,-],[ZC1230;G28,Me,H,H,-],[ZC1231;G28,Et,H,H,-],[ZC1232;G28,Pr,H,H,-],[ZC1233;G28,i-Pr,H,H,-],[ZC1234;G28,CF3,H,H,-],[ZC1235;G28,c-Pr,H,H,-],[ZC1236;G28,Me,Me,H,-],[ZC1237;G28,Me,Et,H,-],[ZC1238;G28,Me,Pr,H,-],[ZC1239;G28,Me,i-Pr,H,-],[ZC1240;G28,Me,OMe,H,-],[ZC1241;G28,Me,CF3,H,-],[ZC1242;G28,Me,F,H,-],[ZC1243;G28,Me,Cl,H,-],[ZC1244;G28,Me,CN,H,-],[ZC1245;G28,Me,Ph,H,-],[ZC1246;G28,Me,c-Pr,H,-],[ZC1247;G28,Me,H,Me,-],[ZC1248;G28,Me,H,Et,-],[ZC1249;G28,Me,H,Pr,-],[ZC1250;G28,Me,H,i-Pr,-],[ZC1251;G28,Me,H,OMe,-],[ZC1252;G28,Me,H,CF3,-],[ZC1253;G28,Me,H,F,-],[ZC1254;G28,Me,H,Cl,-],[ZC1255;G28,Me,H,CN,-],[ZC1256;G28,Me,H,c-Pr,-],[ZC1257;G29,H,H,H,-],[ZC1258;G29,Me,H,H,-],[ZC1259;G29,Et,H,H,-],[ZC1260;G29,Pr,H,H,-],[ZC1261;G29,i-Pr,H,H,-],[ZC1262;G29,OMe,H,H,-],[ZC1263;G29,CF3,H,H,-],[ZC1264;G29,F,H,H,-],[ZC1265;G29,Cl,H,H,-],[ZC1266;G29,CN,H,H,-],[ZC1267;G29,c-Pr,H,H,-],[ZC1268;G29,H,Me,H,-],[ZC1269;G29,H,Et,H,-],[ZC1270;G29,H,Pr,H,-],[ZC1271;G29,H,i-Pr,H,-],[ZC1272;G29,H,OMe,H,-],[ZC1273;G29,H,CF3,H,-],[ZC1274;G29,H,F,H,-],[ZC1275;G29,H,Cl,H,-],[ZC1276;G29,H,CN,H,-],[ZC1277;G29,H,Ph,H,-],[ZC1278;G29,H,c-Pr,H,-],[ZC1279;G29,H,H,Me,-],[ZC1280;G29,H,H,Et,-],[ZC1281;G29,H,H,Pr,-],[ZC1282;G29,H,H,i-Pr,-],[ZC1283;G29,H,H,OMe,-],[ZC1284;G29,H,H,CF3,-],[ZC1285;G29,H,H,F,-],[ZC1286;G29,H,H,Cl,-],[ZC1287;G29,H,H,CN,-],[ZC1288;G29,H,H,Ph,-],[ZC1289;G29,H,H,c-Pr,-],[ZC1290;G30,H,H,-,-],[ZC1291;G30,Me,H,-,-],[ZC1292;G30,Et,H,-,-],[ZC1293;G30,Pr,H,-,-],[ZC1294;G30,i-Pr,H,-,-],[ZC1295;G30,OMe,H,-,-],[ZC1296;G30,CF3,H,-,-],[ZC1297;G30,F,H,-,-],[ZC1298;G30,Cl,H,-,-],[ZC1299;G30,CN,H,-,-],[ZC1300;G30,c-Pr,H,-,-],;

[1047] [ZC1301;G30,H,Me,-,-],[ZC1302;G30,H,Et,-,-],[ZC1303;G30,H,Pr,-,-],[ZC1304;G30,H,i-Pr,-,-],[ZC1305;G30,H,OMe,-,-],[ZC1306;G30,H,CF3,-,-],[ZC1307;G30,H,F,-,-],[ZC1308;G30,H,Cl,-,-],[ZC1309;G30,H,CN,-,-],[ZC1310;G30,H,Ph,-,-],[ZC1311;G30,H,c-Pr,-,-],[ZC1312;G31,H,H,H,-],[ZC1313;G31,Me,H,H,-],[ZC1314;G31,Et,H,H,-],[ZC1315;G31,Pr,H,H,-],[ZC1316;G31,i-Pr,H,H,-],[ZC1317;G31,CF3,H,H,-],[ZC1318;G31,c-Pr,H,H,-],[ZC1319;G31,Me,Me,H,-],[ZC1320;G31,Me,Et,H,-],[ZC1321;G31,Me,Pr,H,-],[ZC1322;G31,Me,i-Pr,H,-],[ZC1323;G31,Me,OMe,H,-],[ZC1324;G31,Me,CF3,H,-],[ZC1325;G31,Me,F,H,-],[ZC1326;G31,Me,Cl,H,-],[ZC1327;G31,Me,CN,H,-],[ZC1328;G31,Me,Ph,H,-],[ZC1329;G31,Me,c-Pr,H,-],[ZC1330;G31,Me,H,Me,-],[ZC1331;G31,Me,H,Et,-],[ZC1332;G31,Me,H,Pr,-],[ZC1333;G31,Me,H,i-Pr,-],[ZC133...

Claims

1. Compounds represented by formula (I) or their salts, [Chemical Formula 1] In formula (I), the combination of X and L represents: X is a nitrogen atom and L is an oxygen atom or NH, or X is CH and L is an oxygen atom; n represents 1 or 2, E represents phenyl, pyridinyl, thiophene, thiazolyl, pyrazolyl, R 3 -ON=C(R) 4 )-, or R 6 O-, where The phenyl group may be substituted by one or more substituents selected from group H; the pyridyl, thiophene, thiazolyl, and pyrazolyl groups may be substituted by one or more substituents selected from group K; R 1 and R 2 R represents methyl. 3 R indicates methyl or ethyl. 4 R represents a methyl group or a hydrogen atom. 6 The group H represents butyl, which consists of C1-C3 chain hydrocarbon groups, C1-C3 alkoxy groups, trifluoromethoxy groups, C3-C4 cycloalkyl groups, halogen atoms, cyano groups, and nitro groups, wherein the C1-C3 chain hydrocarbon group may be substituted by one or more halogen atoms. The group K represents C1-C3 chain hydrocarbon groups and halogen atoms, wherein the C1-C3 chain hydrocarbon group may be substituted by one or more halogen atoms.

2. A pesticide composition comprising the compound of claim 1 or its salts and an inactive support.

3. A composition comprising one or more components selected from the groups (a), (b), (c) and (d), and the compound or salt thereof as claimed in claim 1, wherein group (a) is composed of an insecticidal active ingredient, an acaricidal active ingredient and a nematicidal active ingredient; group (b) is a bactericidal active ingredient; group (c) is a plant growth regulator; and group (d) is a repellent ingredient.

4. A method for controlling soybean rust fungus with an amino acid substitution of F129L in mitochondrial cytochrome b protein, which is carried out by applying an effective amount of the compound of claim 1 or its salts or the composition of claim 3 to soybeans or the soil for soybean growth.

5. The compound represented by formula (II), [Chemical Formula 2] In formula (II), the combination of X and L represents: X being a nitrogen atom and L being an oxygen atom or NH, or X being CH and L being an oxygen atom; E a R represents 12a C(O)-, R 12a C (=N-OH)-, hydroxyl group, 4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl group, or halogen atom, R 1a and R 2a R represents methyl. 12a It represents a methyl group or a hydrogen atom.

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