Nitrogen-containing heterocyclic compound and method for controlling plant diseases
Nitrogen-containing heterocyclic compounds effectively address the inadequacies of existing disease control methods by offering robust protection and growth promotion for plants.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- SUMITOMO CHEM CO LTD
- Filing Date
- 2025-10-29
- Publication Date
- 2026-05-07
AI Technical Summary
Existing methods for controlling plant diseases are inadequate in effectiveness and efficiency.
The use of nitrogen-containing heterocyclic compounds, represented by specific chemical structures, for treating plants or soil to control plant diseases, including their application in formulations with inert carriers and as seed treatments.
The nitrogen-containing heterocyclic compounds demonstrate excellent control efficacy against plant diseases, providing effective protection and potentially enhancing plant growth.
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Figure JP2025037988_07052026_PF_FP_ABST
Abstract
Description
Nitrogen-containing heterocyclic compounds and methods for controlling plant diseases
[0001] This application claims priority and benefits of Japanese Patent Application No. 2024-190367, filed on 30 October 2024, and Japanese Patent Application No. 2025-104783, filed on 20 June 2025, the entire contents of which are incorporated herein by reference. The present invention relates to nitrogen-containing heterocyclic compounds and methods for controlling plant diseases.
[0002] Patent Document 1 describes nitrogen-containing heterocyclic compounds.
[0003] International Publication No. 2009 / 156098
[0004] The objective of this invention is to provide an excellent method for controlling plant diseases.
[0005] The present inventors, in an effort to find an excellent method for controlling plant diseases, have discovered that the compound represented by the following formula (I) has excellent control efficacy against plant diseases. That is, the present invention is as follows.
[0006] [1] Equation (I) [In the formula, A and Z 1 The combination is such that A is the group represented by A1, the group represented by A2, the group represented by A3, or the group represented by A4, and Z 1 However, a phenyl group, a 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {the phenyl group and the 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) may be substituted with one or more substituents selected from group A}, a C3-C6 alicyclic hydrocarbon group, a 3-6 member non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}, OR 3 , SR 4 S(O)R 5 , or S(O)2R 6 The combination is; or, A is the base represented by A5, and Z 1is a 5- to 6-membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazol-3-yl group) {the 5- to 6-membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazol-3-yl group) may be substituted with one or more substituents selected from Group A}, a C3-C6 alicyclic hydrocarbon group, a 3- to 6-membered non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3- to 6-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B}, OR 7 , SR 8 , S(O)R 9 , or S(O)2R 10 represents a combination thereof, and the group represented by A1, the group represented by A2, the group represented by A3, the group represented by A4, and the group represented by A5 are each a group represented by the following formula (* represents the bonding site with CR 1 R 2 ), Q 1 , and Q 2 are the same or different and represent an oxygen atom or a sulfur atom, L 1 represents an oxygen atom, a sulfur atom, or NR L1 , G 1 represents a nitrogen atom or CR G1 , G 2 represents a nitrogen atom or CR G2 , G 3 represents a nitrogen atom or CR G3 , G 4 represents a nitrogen atom or CR G4 , G 5 represents a nitrogen atom or CR G5 (however, among G 2 , G 3 , G 4 , and G 5 , the number of nitrogen atoms is 0 or 1), R 1 and R 2 are the same or different and are a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3- to 8-membered non-aromatic heterocyclic group which may be substituted with one or more substituents selected from Group C {the C3-C8 alicyclic hydrocarbon group and the 3- to 8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group D}, OR 17 , NR18 R 19 R represents a halogen atom or a hydrogen atom. 17 R represents a C1-C6 chain hydrocarbon group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group (the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group may be substituted with one or more substituents selected from group F), or a hydrogen atom. 18 and R 19 R represents a C1-C6 chain hydrocarbon group, which may be the same or different in phase and may be substituted with one or more halogen atoms, or a hydrogen atom. 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 R represents a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group D, either identical or different. 11 , R 12 , R 14 , R 15 , R 16 , R G1 , R G2 , R G3 , R G4 and R G5 R represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group C, a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group B, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom, and R 13 R represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group E, a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group B, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom. L1This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group C, a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group B, a cyano group, or a hydrogen atom. Group A: A group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, a C3-C6 alicyclic hydrocarbon group, a 3-6 membered non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group D}, a halogen atom, a cyano group, a nitro group, a sulfanyl group, and a hydroxyl group. Group B: A group consisting of oxo groups, thioxo groups, methyl groups, C2-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups {the C2-C6 chain hydrocarbon groups, the C1-C6 alkoxy groups, the C1-C6 alkylamino groups, and the C2-C8 dialkylamino groups may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups {the C3-C6 alicyclic hydrocarbon groups and the 3-6 membered non-aromatic heterocyclic groups may be substituted with one or more substituents selected from Group D}, halogen atoms, cyano groups, nitro groups, sulfanyl groups, and hydroxyl groups. Group C: A group consisting of C1-C6 alkoxy groups, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups (the C3-C6 alicyclic hydrocarbon groups and the 3-6 membered non-aromatic heterocyclic groups may be substituted with one or more substituents selected from Group D), halogen atoms, cyano groups, nitro groups, and hydroxyl groups. Group D: A group consisting of oxo groups, thioxo groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups (the C1-C6 chain hydrocarbon groups and the C1-C6 alkoxy groups may be substituted with one or more halogen atoms), hydroxyl groups, halogen atoms, and cyano groups.A method for controlling plant diseases comprising treating plants or soil on which plants are cultivated with a compound represented by [Formula (II)] (hereinafter referred to as Compound N), its N oxide, or a salt thereof (hereinafter referred to as Compound N, its N oxide, or a salt thereof) [Formula (II)]. [Formula (II)]. [In the formula, A a and Z a The combination is A a A2 a The base shown, A3 a The base indicated by, or A4 a The base is represented by Z a However, group G a A phenyl group, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) which may be substituted with one or more substituents selected from group A. a Group F a Cyclopropyl groups substituted with one or more more selected substituents, Group B a A C5-C6 alicyclic hydrocarbon group, or OR, which may be substituted with one or more more selected substituents. 3a The combination is A a is A5 a The base is represented by Z a However, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A awhich may be substituted with one or more substituents selected from}, group F a A cyclopropyl group substituted with one or more substituents selected from, group B a A C5-C6 cycloalkenyl group which may be substituted with one or more substituents selected from, or OR 4a represents a combination that is, A2 a a group represented by, A3 a a group represented by, A4 a a group represented by, and A5 a a group represented by each represents a group represented by the following formula (# represents the bonding site with CR 1a R 2a ), Q 2a , and L 1a are the same or different and represent an oxygen atom or a sulfur atom, G 1a represents a nitrogen atom or CR G1a , G 2a represents a nitrogen atom or CR G2a , G 3a represents a nitrogen atom or CR G3a , G 4a represents a nitrogen atom or CR G4a , G 5a represents a nitrogen atom or CR G5a represents (however, among G 2a , G 3a , G 4a , and G 5a the number of nitrogen atoms is 0 or 1), R 1a and R 2a are the same or different and are a C1-C4 chain hydrocarbon group, a C3-C6 alicyclic hydrocarbon group, or a 3-5 member non-aromatic heterocyclic group which may be substituted with one or more substituents selected from group C a {the C3-C6 alicyclic hydrocarbon group and the 3-5 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group D a}, OR 10a , a halogen atom, or a hydrogen atom, R 10a is group H aR represents a C1-C6 chain hydrocarbon group which may be substituted with one or more more selected substituents, a (C1-C6 alkyl) carbonyl group which may be substituted with one or more halogen atoms, or a hydrogen atom. 3a and R 4a These are the same or different, group D a R represents a C4-C6 alicyclic hydrocarbon group which may be substituted with one or more more selected substituents. 6a , R 8a , R 9a , R G1a , R G2a , R G4a and R G5a These are the same or different, group E a C1-C4 chain hydrocarbon groups, group B, which may be substituted with one or more more selected substituents. a R represents a C3-C4 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom, which may be substituted with one or more more selected substituents. 7a is group E a C1-C3 chain hydrocarbon groups, group B, which may be substituted with one or more more selected substituents. a R represents a C3-C4 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom, which may be substituted with one or more more selected substituents. G3a This refers to C1-C4 chain hydrocarbon groups, group B. a This represents a C3-C4 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a nitro group, a halogen atom, or a hydrogen atom, which may be substituted with one or more more selected substituents. Group A a : Methyl group, CFH2 group, CF2H group, C2-C6 chain hydrocarbon group, C1-C6 alkoxy group {The C2-C6 chain hydrocarbon group and the C1-C6 alkoxy group may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon group, 3-6 membered non-aromatic heterocyclic group {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group D aGroup B: A group consisting of halogen atoms, cyano groups, nitro groups, and sulfanyl groups, which may be substituted with one or more more selected substituents. a : Oxo group, thioxo group, C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C8 dialkylamino group, {The C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon group, 3-6 membered non-aromatic heterocyclic group {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group D a A group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, and sulfanyl groups, which may be substituted with one or more more selected substituents. Group C a : A C1-C6 alkoxy group, a C3-C6 alicyclic hydrocarbon group, or a 3-6 membered non-aromatic heterocyclic group which may be substituted with one or more halogen atoms {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group D a A group consisting of halogen atoms, cyano groups, nitro groups, and hydroxyl groups, which may be substituted with one or more more selected substituents. Group D a : A group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, {the C1-C6 chain hydrocarbon group and the C1-C6 alkoxy group may be substituted with one or more halogen atoms}, a hydroxyl group, a halogen atom, and a cyano group. Group E a : A C1-C6 alkoxy group which may be substituted with one or more halogen atoms, and a C3-C6 alicyclic hydrocarbon group {The C3-C6 alicyclic hydrocarbon group is from group D a A group consisting of {which may be substituted with one or more substituents selected from}. Group F a : A group consisting of C1-C6 chain hydrocarbon groups, C3-C6 alicyclic hydrocarbon groups, cyano groups, and halogen atoms, which may be substituted with one or more halogen atoms. Group G a: C1-C6 chain hydrocarbon group, C2-C6 alkoxy group {The C1-C6 chain hydrocarbon group and the C2-C6 alkoxy group may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon group, 3-6 membered non-aromatic heterocyclic group {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group D a A group consisting of halogen atoms, cyano groups, nitro groups, and hydroxyl groups, which may be substituted with one or more more selected substituents. Group H a : A group consisting of a phenyl group which may be substituted with one or more halogen atoms, and halogen atoms. ] A compound represented by (hereinafter referred to as the present invention compound N), or its N oxide or a salt thereof (hereinafter referred to as the present invention compound N, its N oxide or a salt thereof). [3] A a A2 a It is a base represented by Q 2a The compound described in [2], or its N oxide, or a salt thereof, wherein the N atom is an oxygen atom. [4] A a A4 a The group shown is G 1a[2] The compound or its N oxide or a salt thereof, wherein the compound is CH. [5] A composition containing the compound or its N oxide or a salt thereof, as described in any of [2] to [4], and an inert carrier. [6] A composition containing one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound or its N oxide or a salt thereof, as described in any of [2] to [4]: Group (a): A group consisting of an insecticidal component, acaricidal component, and nematicidal component; Group (b): A bactericidal component; Group (c): A plant growth regulating component; Group (d): A repellent component. [7] A method for controlling plant diseases, comprising treating a plant or soil on which a plant is cultivated with an effective amount of the compound or its N oxide or a salt thereof, as described in any of [2] to [4], or an effective amount of the composition described in [6]. [8] Use of any of the compounds described in [2] to [4], their N oxides, or salts thereof, or the composition described in [6], for the control of plant diseases. [9] Seeds or vegetative reproductive organs containing an effective amount of any of the compounds described in [2] to [4], their N oxides, or salts thereof, or an effective amount of the composition described in [6].
[0007] This invention makes it possible to control plant diseases.
[0008] The substituents in this invention will now be described. A halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. When a substituent is substituted with two or more halogen atoms or substituents, those halogen atoms or substituents may be the same or different. In this specification, "may be substituted with one or more substituents selected from group X" (where X is A, B, C, D, E, F, A a , B a , C a , D a , E a F a G a H a A 2 , B 2 A 2a , B 2a and F 2aThe notation (meaning any one of the above) means that if there are two or more substituents selected from group X, those substituents may be the same or different. In this specification, the notation "CX-CY" means that the number of carbon atoms is X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 to 6. A chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl groups. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl groups. Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl groups. Examples of C1-C6 alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups. Examples of C1-C6 haloalkoxy groups include monofluoromethoxy, difluoromethoxy, trifluoromethoxy, dichloromethoxy, trichloromethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 3,3,3-trifluoropropoxy, 1,1,1,3,3,3-hexafluoro-2-propoxy, 4,4,4-trifluorobutoxy, 5,5,5-trifluoropentyloxy, and 6,6,6-trifluorohexyloxy. Examples of (C1-C6 alkyl)carbonyl groups include formyl, acetyl, propionyl, acryloyl, butyryl, isobutyryl, pentanoyl, and hexanoyl.Examples of (C1-C6 alkoxy)carbonyl groups include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, and hexyloxycarbonyl group. Examples of C1-C6 alkylamino groups include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, tert-butylamino group, pentylamino group, and hexylamino group. Examples of C2-C8 dialkylamino groups include dimethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, dibutylamino group, ethylmethylamino group, methylpropylamino group, isopropylmethylamino group, butylmethylamino group, ethylpropylamino group, ethylisopropylamino group, butylethylamino group, isopropylpropylamino group, butylpropylamino group, and butylisopropylamino group. Examples of alicyclic hydrocarbon groups include cycloalkyl groups and cycloalkenyl groups. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups. Examples of cycloalkenyl groups include cyclopentenyl, cyclohexenyl, cycloheptenyl, and cyclooctenyl groups.Examples of non-aromatic heterocyclic groups include azilidinyl group, oxyranyl group, thyranyl group, azetidinyl group, oxetanyl group, thietanyl group, pyrrolidinyl group, tetrahydrofuranyl group, tetrahydrothienyl group, pyrazolinyl group, pyrazolidinyl group, imidazolinyl group, imidazolidinyl group, oxazolinyl group, thiazolinyl group, oxazolidinyl group, thiazolidinyl group, and isoxazolidinyl group. Examples include isoxazolidinyl group, isothiazolinyl group, isothiazolidinyl group, dioxolanyl group, dioxanyl group, piperidyl group, piperazinyl group, morpholinyl group, thiomorpholinyl group, pyranyl group, dihydropyranyl group, tetrahydropyranyl group, tetrahydrothiopyranyl group, azepanyl group, oxepanyl group, thiepanyl group, azokanyl group, oxokanyl group, and thiokanyl group. Examples of aromatic heterocyclic groups include five-membered aromatic heterocyclic groups such as pyrrolyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, and thiadiazolyl groups; and six-membered aromatic heterocyclic groups such as pyridyl, pyridadinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetradinyl groups.
[0009] Examples of the bases shown in A5 are formulas T1, T2, T3, T4, and T5. The bases shown in the formula [wherein the formula, the symbols have the same meaning as above] are examples.
[0010] A5 a Examples of the base shown are, for example, formula T1 a , T2 a , T3 a , T4 a and T5 a The bases shown in the formula [wherein the formula, the symbols have the same meaning as above] are examples.
[0011] The N oxide of a compound represented by formula (I) or formula (II) refers to a structure in which at least one nitrogen atom in the compound represented by formula (I) or formula (II) is substituted with an oxo group.
[0012] The compound in question or the compound of the present invention may have one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. The present invention includes each stereoisomer and mixtures of stereoisomers in any ratio.
[0013] Compounds represented by formula (I) or formula (II), or their N oxides, may form acid addition salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, and benzoate when mixed with acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid.
[0014] Examples of the compound N include the following compounds.
[0015] [Aspect 1] In compound N, Z 1 A compound in which the phenyl group or a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {the phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) may be substituted with one or more substituents selected from group A}. [Aspect 2] In compound N, Z 1 However, a compound which is a phenyl group that may be substituted with one or more substituents selected from group A. [Aspect 3] In compound N, Z 1 However, a compound having a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) may be substituted with one or more substituents selected from group A}. [Aspect 4] In the compound N, Z 1 However, a phenyl group or a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {The phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) belong to group A 2 Compounds which may be substituted with one or more more selected substituents. Group A 2: A group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, {the C1-C6 chain hydrocarbon group and the C1-C6 alkoxy group may be substituted with one or more halogen atoms}, and a halogen atom. [Aspect 5] In the compound N, Z 1 However, Group A 2 A compound which is a phenyl group that may be substituted with one or more more selected substituents. [Aspect 6] In compound N, Z 1 However, a 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {The 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) belongs to group A 2 A compound which may be substituted with one or more more selected substituents. [Aspect 7] In the compound N, Z 1 However, a compound which is a C3-C6 alicyclic hydrocarbon group that may be substituted with one or more substituents selected from group B. [Aspect 8] In this compound N, Z 1 However, the compound is a 3-6 member non-aromatic heterocyclic group which may be substituted with one or more substituents selected from group B. [Aspect 9] In the compound N, Z 1 However, Group B 2 A compound that is a C3-C6 alicyclic hydrocarbon group, which may be substituted with one or more more selected substituents. Group B 2 : A group consisting of an oxo group, a thioxo group, a methyl group, a C2-C6 chain hydrocarbon group, and a C3-C6 alicyclic hydrocarbon group {the C2-C6 chain hydrocarbon group and the C3-C6 alicyclic hydrocarbon group may be substituted with one or more halogen atoms}. [Aspect 10] In the compound N, Z 1 However, Group B 2 A compound which is a 3-6 member non-aromatic heterocyclic group that may be substituted with one or more more selected substituents. [Aspect 11] In the compound N, Z 1 However, OR 20 And R 20 However, a compound which is a C3-C6 alicyclic hydrocarbon group that may be substituted with one or more substituents selected from group D. [Aspect 12] In this compound N, Z 1 However, OR 20 And R 20A compound in which Z is a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more halogen atoms. [Aspect 13] In the compound N, Z 1 However, SR 21 S(O)R 22 , or S(O)2R 23 And R 21 , R 22 and R 23 However, the compound is a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group D, either identical or different. [Aspect 14] In the compound N, Z 1 However, SR 21 S(O)R 22 , or S(O)2R 23 And R 21 , R 22 and R 23 However, a compound which is a C3-C6 alicyclic hydrocarbon group that is the same or different in phase and may be substituted with one or more halogen atoms. [Aspect 15] In the compound N, A and Z 1 The combination is such that A is the group represented by A1, the group represented by A2, the group represented by A3, or the group represented by A4, Z 1 However, a combination of a phenyl group, a 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {the phenyl group and the 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) may be substituted with one or more substituents selected from group A}, a C3-C6 alicyclic hydrocarbon group, or a 3-6 member non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B}; or A is the group represented by A5, and Z 1A compound having a combination of a 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {which may be substituted with one or more substituents selected from group A}, a C3-C6 alicyclic hydrocarbon group, or a 3-6 member non-aromatic heterocyclic group {which may be substituted with one or more substituents selected from group B}. [Aspect 16] In compound N, A and Z 1 The combination is such that A is the group represented by A1, the group represented by A2, the group represented by A3, or the group represented by A4, Z 1 However, the phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {The phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) belong to group A 2 {The C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from the group B}, or a C3-C6 alicyclic hydrocarbon group, or a 3-6 membered non-aromatic heterocyclic group {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group B 2 A combination in which A is a group represented by A5 and Z 1 However, 5-6 member aromatic heterocyclic groups (excluding the 1,2,4-oxadiazole-3-yl group) {The 5-6 member aromatic heterocyclic groups (excluding the 1,2,4-oxadiazole-3-yl group) group A 2 {The C3-C6 alicyclic hydrocarbon group may be substituted with one or more substituents selected from the group B}, or a C3-C6 alicyclic hydrocarbon group, or a 3-6 membered non-aromatic heterocyclic group {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group B 2 A compound which is a combination of which Z may be substituted with one or more substituents selected from the above. [Aspect 17] In compound N, Z 1 However, C3-C6 alicyclic hydrocarbon groups or 3-6 membered non-aromatic heterocyclic groups {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group B 2 A compound which may be substituted with one or more more selected substituents. [Aspect 18] In the compound N, Z 1 However, OR20 , SR 21 S(O)R 22 , or S(O)2R 23 And so, R 20 , R 21 , R 22 and R 23 However, the compound is a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group D, either identical or different. [Aspect 19] In the compound N, Z 1 However, OR 20 , SR 21 S(O)R 22 , or S(O)2R 23 And R 20 , R 21 , R 22 and R 23 However, a compound which is a C3-C6 alicyclic hydrocarbon group that is the same or different in phase and may be substituted with one or more halogen atoms. [Aspect 20] In the compound N, A and Z 1 The combination is such that A is the group represented by A1, the group represented by A2, the group represented by A3, or the group represented by A4, Z 1 However, the phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {The phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) belong to group A 2} or OR may be substituted with one or more more selected substituents 20 And R 20 A combination in which is a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more halogen atoms, or A is the group represented by A5, and Z 1 However, a 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) {The 5-6 member aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group) belongs to group A 2} or OR may be substituted with one or more more selected substituents 20 And R 20A compound in which is a combination of C3-C6 alicyclic hydrocarbon groups which may be substituted with one or more halogen atoms. [Aspect 21] A compound in which A is the group represented by A5 in any of the present compound N, aspects 1, 3, 4, or aspects 6 to 20. [Aspect 22] A compound in which A is the group represented by A5 in any of the present compound N, aspects 1, 3, 4, or aspects 6 to 20, and R G2 , R G3 , R G4 and R G5 A compound in which A is the same or different C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom. [Aspect 23] A compound in which A is a pyridine-2-yl group or a pyrimidine-2-yl group {the pyridine-2-yl group and the pyrimidine-2-yl group may be substituted with a C1-C6 chain hydrocarbon group or halogen atom} in any of the present compound N, aspect 1, aspect 3, aspect 4, or aspects 6 to 20. [Aspect 24] A compound in which A is a pyridine-2-yl group in any of the present compound N, aspect 1, aspect 3, aspect 4, or aspects 6 to 20. [Aspect 25] A compound in which A is a pyrimidine-2-yl group in any of the present compound N, aspect 1, aspect 3, aspect 4, or aspects 6 to 20. [Aspect 26] A compound in which A is the group represented by A1, the group represented by A2, the group represented by A3, or the group represented by A4 in any of the present compound N or aspects 1 to 20. [Aspect 27] In compound N, or any of aspects 1 to 20, A is the group represented by A1, the group represented by A2, the group represented by A3, or the group represented by A4, and R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , and R G1 A compound in which the C1-C6 chain hydrocarbon group or hydrogen atom is the same or different in phase. [Aspect 28] In the present compound N, or any of aspects 1 to 20, A is the group represented by A1, and R 11 , and R 12 However, the compound is the same or different in phase, and is a C1-C6 chain hydrocarbon group or a hydrogen atom. [Aspect 29] In the present compound N, or any of aspects 1 to 20, A is the group represented by A2, and R 13A compound in which is a C1-C6 chain hydrocarbon group or a hydrogen atom. [Aspect 30] In the present compound N, or any of aspects 1 to 20, A is the group represented by A2, and R 13 Q is a C1-C6 chain hydrocarbon group or a hydrogen atom. 2 A compound in which is an oxygen atom. [Aspect 31] In compound N, or any of aspects 1 to 20, A is the group represented by A2, and R 13 Q is a C1-C6 chain hydrocarbon group or a hydrogen atom. 2 A compound in which is a sulfur atom. [Aspect 32] In compound N, or any of aspects 1 to 20, A is the group represented by A3, and R 14 and R 15 However, the compound is identical or different in phase, and is a C1-C6 chain hydrocarbon group or a hydrogen atom. [Aspect 33] In the present compound N, or any of aspects 1 to 20, A is the group represented by A3 and R 14 , and R 15 However, they are the same or different C1-C6 chain hydrocarbon group or hydrogen atom, L 1 NR L1 And R L1 However, a compound which is a C1-C6 chain hydrocarbon group or a hydrogen atom which may be substituted with one or more halogen atoms. [Aspect 34] In the present compound N, or any of aspects 1 to 20, A is the group represented by A3 and R 14 , and R 15 However, they are the same or different C1-C6 chain hydrocarbon group or hydrogen atom, L 1 A compound in which is an oxygen atom or a sulfur atom. [Aspect 35] In compound N, or any of aspects 1 to 20, A is the group represented by A4, and R 16 A compound in which is a C1-C6 chain hydrocarbon group or a hydrogen atom. [Aspect 36] In the present compound N, or any of aspects 1 to 20, A is the group represented by A4, and R 16 is a C1-C6 chain hydrocarbon group or a hydrogen atom, G 1 A compound in which is a nitrogen atom. [Aspect 37] In the present compound N, or any of aspects 1 to 20, A is the group represented by A4 and R 16 is a C1-C6 chain hydrocarbon group or a hydrogen atom, G 1 CRG1 And R G1 A compound in which is a C1-C6 chain hydrocarbon group or a hydrogen atom. [Aspect 38] In compound N, aspect 1, aspect 3, aspect 4, or any of aspects 6 to 20, A is a pyridinyl group, a pyrimidinyl group, a group represented by A1, a group represented by A2, a group represented by A3, or a group represented by A4, and R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 However, the compound is the same or different in phase, and is a C1-C6 chain hydrocarbon group or a hydrogen atom. [Aspect 39] In any of the present compound N, aspects 1, 3, 4, or aspects 6 to 20, A is a group represented by a pyridinyl group, a pyrimidinyl group, A2, or A4, and R 13 and R 16However, the compounds are identical or different in phase, and consist of a C1-C6 chain hydrocarbon group or a hydrogen atom. [Aspect 40] A compound in which A is a 1,2,3-triazole-2-yl group, an oxazole-2-yl group, a thiazole-2-yl group, a 1,2,4-oxadiazole-3-yl group, a 1,2,4-thiadiazole-3-yl group {the 1,2,3-triazole-2-yl group, the oxazole-2-yl group, the thiazole-2-yl group, the 1,2,4-oxadiazole-3-yl group, and the 1,2,4-thiadiazole-3-yl group may be substituted with a C1-C6 hydrocarbon group}, a pyridine-2-yl group, or a pyrimidine-2-yl group {the pyridine-2-yl group and the pyrimidine-2-yl group may be substituted with a C1-C6 hydrocarbon group or a halogen atom}. [Aspect 41] A compound in which A is a 1,2,3-triazole-2-yl group, an oxazole-2-yl group, a thiazole-2-yl group, a 1,2,4-oxadiazole-3-yl group, a 1,2,4-thiadiazole-3-yl group {the 1,2,3-triazole-2-yl group, the oxazole-2-yl group, the thiazole-2-yl group, the 1,2,4-oxadiazole-3-yl group, and the 1,2,4-thiadiazole-3-yl group may be substituted with a C1-C6 chain hydrocarbon group}, a pyridine-2-yl group, or a pyrimidine-2-yl group. [Aspect 42] A compound in which A is a 1,2,3-triazole-2-yl group, a 1,2,4-oxadiazole-3-yl group, a 1,2,4-thiadiazole-3-yl group {the 1,2,3-triazole-2-yl group, the 1,2,4-oxadiazole-3-yl group, and the 1,2,4-thiadiazole-3-yl group may be substituted with a C1-C6 chain hydrocarbon group}, a pyridine-2-yl group, or a pyrimidine-2-yl group.[Aspect 43] A compound in which A is a 1,2,3-triazole-2-yl group, a 1,2,4-oxadiazole-3-yl group {the 1,2,3-triazole-2-yl group and the 1,2,4-oxadiazole-3-yl group may be substituted with a C1-C6 chain hydrocarbon group}, a pyridine-2-yl group, or a pyrimidine-2-yl group. [Aspect 44] In aspect 20, R. 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 45] In aspect 21, R 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 46] In Aspect 22, R 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 47] In aspect 23, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 48] In Aspect 24, R 1 and R 2 However, it is a compound in which the atom is a hydrogen atom. [Aspect 49] In aspect 25, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 50] In aspect 26, R 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 51] In aspect 27, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 52] In aspect 28, R 1 and R 2 However, a compound in which the atom is a hydrogen atom. [Aspect 53] In aspect 29, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 54] In aspect 30, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 55] In aspect 31, R 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 56] In aspect 32, R 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 57] In aspect 33, R 1 and R 2However, a compound that is a hydrogen atom. [Aspect 58] In aspect 34, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 59] In aspect 35, R 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 60] In aspect 36, R 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 61] In aspect 37, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 62] In aspect 38, R 1 and R 2 However, a compound in which the atom is a hydrogen atom. [Aspect 63] In aspect 39, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 64] In aspect 40, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 65] In aspect 41, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 66] In aspect 42, R 1 and R 2 However, a compound that is a hydrogen atom. [Aspect 67] In aspect 43, R 1 and R 2 However, it is a compound that is a hydrogen atom. [Aspect 68] In aspect 20, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 69] In aspect 21, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 70] In aspect 22, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 71] In aspect 23, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 72] In aspect 24, R 1 and R 2However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 73] In aspect 25, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 74] In aspect 26, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 75] In aspect 27, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 76] In aspect 28, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 77] In aspect 29, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 78] In aspect 30, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 79] In aspect 31, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 80] In aspect 32, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 81] In aspect 33, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 82] In aspect 34, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 83] In aspect 35, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 84] In aspect 36, R 1 and R2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 85] In aspect 37, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 86] In aspect 38, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 87] In aspect 39, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 88] In aspect 40, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 89] In aspect 41, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 90] In aspect 42, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 91] In aspect 43, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect 92] In aspect 20, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 93] In aspect 21, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 94] In aspect 22, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 95] In aspect 23, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 96] In aspect 24, R 1 and R 2However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 97] In aspect 25, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 98] In aspect 26, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 99] In aspect 27, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 100] In aspect 28, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 101] In aspect 29, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 102] In aspect 30, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 103] In aspect 31, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 104] In aspect 32, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 105] In aspect 33, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 106] In aspect 34, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 107] In aspect 35, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 108] In aspect 36, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 109] In aspect 37, R 1 and R2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 110] In aspect 38, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 111] In aspect 39, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 112] In aspect 40, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 113] In aspect 41, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 114] In aspect 42, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 115] In aspect 43, R 1 and R 2 However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect 116] In aspect 20, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 117] In aspect 21, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 118] In Aspect 22, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 119] In aspect 23, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 120] In Aspect 24, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 121] In aspect 25, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 122] In Aspect 26, R 1 is a hydrogen atom, R 2A compound in which is a hydroxyl group. [Aspect 123] In aspect 27, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 124] In Aspect 28, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 125] In aspect 29, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 126] In aspect 30, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 127] In aspect 31, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 128] In Aspect 32, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 129] In aspect 33, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 130] In aspect 34, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 131] In aspect 35, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 132] In aspect 36, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 133] In aspect 37, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 134] In aspect 38, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 135] In aspect 39, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 136] In aspect 40, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 137] In aspect 41, R 1is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 138] In aspect 42, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group. [Aspect 139] In aspect 43, R 1 is a hydrogen atom, R 2 A compound in which R is a hydroxyl group. [Aspect 140] In aspect 20, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 141] In aspect 21, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 142] In aspect 22, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 143] In aspect 23, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 144] In aspect 24, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 145] In aspect 25, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 146] In aspect 26, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 147] In aspect 27, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 148] In Aspect 28, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 149] In aspect 29, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 150] In aspect 30, R 1 is a hydrogen atom, R 2A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 151] In aspect 31, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 152] In aspect 32, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 153] In aspect 33, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 154] In aspect 34, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 155] In aspect 35, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 156] In aspect 36, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 157] In aspect 37, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 158] In aspect 38, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 159] In aspect 39, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 160] In aspect 40, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 161] In aspect 41, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 162] In aspect 42, R 1 is a hydrogen atom, R 2 A compound in which is a hydroxyl group or a hydrogen atom. [Aspect 163] In aspect 43, R 1 is a hydrogen atom, R 2 A compound in which the group is a hydroxyl group or a hydrogen atom.
[0016] Examples of the compound N of the present invention include the following compounds.
[0017] [Aspect A1] In compound N of the present invention, A a and Z a The combination is A a A2 a The base shown, A3 a The base indicated by, or A4 a The group is represented by Z a However, group G a A phenyl group or a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) which may be substituted with one or more substituents selected from group A. a A combination which may be substituted with one or more more selected substituents; or A a is A5 a The group is represented by Z a However, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A a A compound which is a combination in which A may be substituted with one or more substituents selected from the above. [Aspect A2] In compound N of the present invention, A a A2 a The base shown, A3 a The base indicated by, or A4 a The group is represented by Z a However, group G a A compound which is a phenyl group that may be substituted with one or more more selected substituents. [Aspect A3] In compound N of the present invention, A a A2 a The base shown, A3 a The base shown is A4 a The base indicated by, or A5 a The group is represented by Z aHowever, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A a A compound which may be substituted with one or more more selected substituents. [Aspect A4] In compound N of the present invention, A a and Z a The combination is A a A2 a The base shown, A3 a The base indicated by, or A4 a The group is represented by Z a However, a phenyl group or a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belong to group A 2a A combination which may be substituted with one or more more selected substituents; or A a This is the base shown in A5, and Z a However, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A 2a Compounds that are combinations of which may be substituted with one or more more selected substituents. Group A 2a : A group consisting of a methyl group, a CFH2 group, a CF2H group, and a halogen atom. [Aspect A5] In compound N of the present invention, A a A2 a The base shown, A3 a The base indicated by, or A4 a The group is represented by Z a However, Group A 2a A compound which is a phenyl group that may be substituted with one or more more selected substituents. [Aspect A6] In compound N of the present invention, A a A2 a The base shown, A3 a The base shown is A4a The base indicated by, or A5 a The group is represented by Z a However, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A 2a A compound which may be substituted with one or more substituents selected from the above. [Aspect A7] In compound N of the present invention, A a A2 a The base shown, A3 a The base shown is A4 a The base indicated by, or A5 a The group is represented by Z a However, group F a A compound in which a cyclopropyl group is substituted with one or more more selected substituents. [Aspect A8] In compound N of the present invention, A a A2 a The base shown, A3 a The base shown is A4 a The base indicated by, or A5 a The group is represented by Z a However, group F 2a Compounds in which a cyclopropyl group is substituted with one or more more selective substituents. Group F 2a : A group consisting of C1-C6 chain hydrocarbon groups and C3-C6 alicyclic hydrocarbon groups. [Aspect A9] In compound N of the present invention, A a and Z a The combination is A a A2 a The base shown, A3 a The base indicated by, or A4 a The group is represented by Z a However, Group B a A combination of C5-C6 alicyclic hydrocarbon groups which may be substituted with one or more more selected substituents; or A a is A5 a The group is represented by Z a However, Group B aA compound which is a combination of C5-C6 cycloalkenyl groups which may be substituted with one or more more selected substituents. [Aspect A10] In compound N of the present invention, A a and Z a The combination is A a A2 a The base shown, A3 a The base indicated by, or A4 a The group is represented by Z a However, Group B 2a A combination of C5-C6 alicyclic hydrocarbon groups which may be substituted with one or more more selected substituents; or A a is A5 a The group is represented by Z a However, Group B 2a Compounds that are a combination of C5-C6 cycloalkenyl groups, which may be substituted with one or more more selected substituents. Group B 2a : A group consisting of an oxo group, a thioxo group, and a C1-C6 chain hydrocarbon group. [Aspect A11] In compound N of the present invention, A a A2 a The base shown, A3 a The base shown is A4 a The base indicated by, or A5 a The group is represented by Z a However, OR 11a And R 11a However, group D a A compound which is a C4-C6 alicyclic hydrocarbon group that may be substituted with one or more more selected substituents. [Aspect A12] In compound N of the present invention, A a A2 a The base shown, A3 a The base shown is A4 a The base indicated by, or A5 a The group is represented by Z a However, OR 11a And R 11a However, a compound which is a C4-C6 alicyclic hydrocarbon group which may be substituted with one or more halogen atoms. [Aspect A13] In compound N of the present invention, A a and Z a The combination is A a A2 a The base shown, A3a The base indicated by, or A4 a The group is represented by Z a However, group G a A phenyl group, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) which may be substituted with one or more substituents selected from group A. a Group F a A cyclopropyl group substituted with one or more more selected substituents, or group B a A combination of C5-C6 alicyclic hydrocarbon groups which may be substituted with one or more more selected substituents; or A a is A5 a The group is represented by Z a However, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A a Group F a A cyclopropyl group substituted with one or more more selected substituents, or group B a A compound which is a combination of C5-C6 cycloalkenyl groups which may be substituted with one or more more selected substituents. [Aspect A14] In compound N of the present invention, A a and Z a The combination is A a A2 a The base shown, A3 a The base indicated by, or A4 a The group is represented by Z a However, the phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belong to group A 2aGroup F 2a A cyclopropyl group substituted with one or more more selected substituents, or group B 2a A combination of C5-C6 alicyclic hydrocarbon groups which may be substituted with one or more more selected substituents; or A a is A5 a The group is represented by Z a However, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A 2a Group F 2a A cyclopropyl group substituted with one or more more selected substituents, or group B 2a A compound which is a combination of C5-C6 cycloalkenyl groups which may be substituted with one or more more selected substituents. [Aspect A15] In compound N of the present invention, A a and Z a The combination is A a A2 a The base shown, A3 a The base indicated by, or A4 a The group is represented by Z a However, the phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The phenyl group and the 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belong to group A 2a} or OR may be substituted with one or more more selected substituents 11a And R 11a However, a combination of C4-C6 alicyclic hydrocarbon groups which may be substituted with one or more halogen atoms; or A a is A5 a The group is represented by Z aHowever, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A 2a} or OR may be substituted with one or more more selected substituents 11a And R 11a A compound which is a combination of C4-C6 alicyclic hydrocarbon groups which may be substituted with one or more halogen atoms. [Aspect A16] In any of the present invention's compound N, aspects A1, A3, A4, or aspects A6 to A15, A a is A5 a A compound that is a group represented by [Aspect A17] In any of the present invention's compound N, aspects A1, A3, A4, or aspects A6 to A15, A a is A5 a The group is represented by R G2 , R G3 , R G4 and R G5 However, a compound which is the same or different in phase, a C1-C4 chain hydrocarbon group, a halogen atom, or a hydrogen atom. [Aspect A18] In any of the present invention's compound N, aspects A1, A3, A4, or A6 to A15, A a A compound in which the pyridine-2-yl group or pyrimidine-2-yl group {the pyridine-2-yl group and the pyrimidine-2-yl group may be substituted with a C1-C4 chain hydrocarbon group or a halogen atom}. [Aspect A19] In any of the present invention compound N, aspect A1, aspect A3, aspect A4, or aspects A6 to A15, A a However, a compound which is a pyridine-2-yl group or a pyrimidine-2-yl group. [Aspect A20] In any of the present invention compound N, aspects A1, A3, A4, or aspects A6 to A15, A a A compound in which is a pyridine-2-yl group. [Aspect A21] In any of the present invention's compound N, aspects A1, A3, A4, or aspects A6 to A15, A a A compound in which is a pyrimidine-2-yl group. [Aspect A22] Compound N of the present invention, or any of aspects A1 to A15, A aHowever, A2 a The base represented by A3 a A base represented by A4 a A compound that is a group represented by [Aspect A23] Compound N of the present invention, or any of aspects A1 to A15, A a However, A2 a The base represented by A3 a A base represented by A4 a It is a group represented by R 6a , R 7a , R 8a , R 9a , and R G1a However, a compound which is the same or different in phase, and is a C1-C3 chain hydrocarbon group or a hydrogen atom. [Aspect A24] Compound N of the present invention, or any of aspects A1 to A15, A a A2 a The group is represented by R 6a A compound in which is a C1-C3 chain hydrocarbon group or a hydrogen atom. [Aspect A25] Compound N of the present invention, or any of aspects A1 to A15, A a A2 a The group is represented by R 6a Q is a C1-C3 chain hydrocarbon group or a hydrogen atom. 2a A compound in which is an oxygen atom. [Aspect A26] Compound N of the present invention, or any of aspects A1 to A15, A a A2 a The group is represented by R 6a Q is a C1-C3 chain hydrocarbon group or a hydrogen atom. 2a A compound in which is a sulfur atom. [Aspect A27] Compound N of the present invention, or any of aspects A1 to A15, A a A3 a The group is represented by R 7a and R 8a However, a compound which is the same or different in phase, and is a C1-C3 chain hydrocarbon group or a hydrogen atom. [Aspect A28] Compound N of the present invention, or any of aspects A1 to A15, A a A4 a The group is represented by R 9aA compound in which is a C1-C3 chain hydrocarbon group or a hydrogen atom. [Aspect A29] Compound N of the present invention, or any of aspects A1 to A15, A a A4 a The group is represented by R 9a is a C1-C3 chain hydrocarbon group or a hydrogen atom, G 1a A compound in which is a nitrogen atom. [Aspect A30] Compound N of the present invention, or any of aspects A1 to A15, A a A4 a The group is represented by R 9a is a C1-C3 chain hydrocarbon group or a hydrogen atom, G 1a CR G1a And R G1a A compound in which is a C1-C3 chain hydrocarbon group or a hydrogen atom. [Aspect A31] In any of the present invention's compound N, aspects A1, A3, A4, or A6 to A15, A a However, pyridine-2-yl group, pyrimidine-2-yl group, A2 a The base represented by A3 a A base represented by A4 a It is a group represented by R 6a , R 7a , R 8a , R 9a , and R G1a However, a compound which is the same or different in phase, and is a C1-C3 chain hydrocarbon group or a hydrogen atom. [Aspect A32] In any of the present invention's compound N, aspects A1, A3, A4, or A6 to A15, A a However, pyridine-2-yl group, pyrimidine-2-yl group, A2 a A base represented by A4 a It is a group represented by R 6a , R 9a , and R G1a However, a compound which is the same or different in phase, and is a C1-C3 chain hydrocarbon group or a hydrogen atom. [Aspect A33] In any of the present invention's compound N, aspects A1, A3, A4, or A6 to A15, A aA compound wherein the compound is a 1,2,3-triazole-2-yl group, a 1,2,4-oxadiazole-3-yl group, a 1,2,4-thiadiazole-3-yl group {the 1,2,3-triazole-2-yl group, the 1,2,4-oxadiazole-3-yl group, and the 1,2,4-thiadiazole-3-yl group may be substituted with a C1-C3 chain hydrocarbon group}, a pyridine-2-yl group, or a pyrimidine-2-yl group {the pyridine-2-yl group and the pyrimidine-2-yl group may be substituted with a C1-C3 chain hydrocarbon group or a halogen atom}. [Aspect A34] In any of the present invention's compound N, aspects A1, A3, A4, or aspects A6 to A15, A a A compound which is a 1,2,3-triazole-2-yl group, a 1,2,4-oxadiazole-3-yl group, a 1,2,4-thiadiazole-3-yl group {the 1,2,3-triazole-2-yl group, the 1,2,4-oxadiazole-3-yl group, and the 1,2,4-thiadiazole-3-yl group may be substituted with a C1-C3 chain hydrocarbon group}, a pyridine-2-yl group, or a pyrimidine-2-yl group. [Aspect A35] In any of the present invention's compound N, aspects A1, A3, A4, or A6 to A15, A a However, a compound which is a 1,2,3-triazole-2-yl group, a 1,2,4-oxadiazole-3-yl group, {the 1,2,3-triazole-2-yl group and the 1,2,4-oxadiazole-3-yl group may be substituted with a C1-C3 chain hydrocarbon group}, a pyridine-2-yl group, or a pyrimidine-2-yl group. [Aspect A36] In aspect A16, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A37] In aspect A17, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A38] In aspect A18, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A39] In aspect A19, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A40] In aspect A20, R 1a and R 2aHowever, a compound that is a hydrogen atom. [Aspect A41] In aspect A21, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A42] In Aspect A22, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A43] In Aspect A23, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A44] In Aspect A24, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A45] In Aspect A25, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A46] In Aspect A26, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A47] In Aspect A27, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A48] In Aspect A28, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A49] In Aspect A29, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A50] In aspect A30, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A51] In aspect A31, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A52] In aspect A32, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A53] In aspect A33, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A54] In Aspect A34, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A55] In aspect A35, R 1a and R 2a However, it is a compound that is a hydrogen atom. [Aspect A56] In aspect A16, R 1a and R 2aHowever, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A57] In aspect A17, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A58] In aspect A18, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A59] In aspect A19, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A60] In aspect A20, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A61] In aspect A21, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A62] In aspect A22, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A63] In aspect A23, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A64] In aspect A24, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A65] In aspect A25, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A66] In aspect A26, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A67] In aspect A27, R 1a and R 2aHowever, a compound which is the same or different in phase, and is a hydroxyl group, halogen atom, or hydrogen atom. [Aspect A68] In aspect A28, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A69] In aspect A29, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A70] In aspect A30, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A71] In aspect A31, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A72] In aspect A32, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A73] In aspect A33, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A74] In aspect A34, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A75] In aspect A35, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group, a halogen atom, or a hydrogen atom. [Aspect A76] In aspect A16, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A77] In aspect A17, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A78] In aspect A18, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A79] In aspect A19, R 1a and R2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A80] In aspect A20, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A81] In aspect A21, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A82] In aspect A22, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A83] In aspect A23, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A84] In aspect A24, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A85] In aspect A25, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A86] In aspect A26, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A87] In aspect A27, R 1a and R 2a However, a compound which is the same or different, and is a hydroxyl group or a hydrogen atom. [Aspect A88] In aspect A28, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A89] In aspect A29, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A90] In aspect A30, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A91] In aspect A31, R 1a and R 2aHowever, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A92] In aspect A32, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A93] In aspect A33, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A94] In aspect A34, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A95] In aspect A35, R 1a and R 2a However, a compound which is the same or different in phase, and is a hydroxyl group or a hydrogen atom. [Aspect A96] In aspect A16, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group. [Aspect A97] In aspect A17, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group. [Aspect A98] In Aspect A18, R 1a is a hydrogen atom, R 2a A compound in which R is a hydroxyl group. [Aspect A99] In Aspect A19, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group. [Aspect A100] In Aspect A20, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group. [Aspect A101] In aspect A21, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group. [Aspect A102] In Aspect A22, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group. [Aspect A103] In Aspect A23, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group. [Aspect A104] In Aspect A24, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group. [Aspect A105] In aspect A25, R1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A106] In aspect A26, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A107] In aspect A27, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A108] In aspect A28, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A109] In aspect A29, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A110] In aspect A30, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A111] In aspect A31, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A112] In aspect A32, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A113] In aspect A33, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A114] In aspect A34, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A115] In aspect A35, R 1a is a hydrogen atom, and R 2a is a hydroxy group. [Aspect A116] In aspect A16, R 1a is a hydrogen atom, and R 2a is a hydroxy group or a hydrogen atom. [Aspect A117] In aspect A17, R 1a is a hydrogen atom, and R 2a is a hydroxy group or a hydrogen atom. [Aspect A118] In aspect A18, R 1a is a hydrogen atom, and R 2a is a hydroxy group or a hydrogen atom. [Aspect A119] In aspect A19, R1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A120] In aspect A20, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A121] In aspect A21, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A122] In Aspect A22, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A123] In aspect A23, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A124] In Aspect A24, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A125] In aspect A25, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A126] In aspect A26, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A127] In aspect A27, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A128] In Aspect A28, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A129] In Aspect A29, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A130] In aspect A30, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A131] In aspect A31, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A132] In aspect A32, R 1ais a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A133] In aspect A33, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A134] In aspect A34, R 1a is a hydrogen atom, R 2a A compound in which is a hydroxyl group or a hydrogen atom. [Aspect A135] In aspect A35, R 1a is a hydrogen atom, R 2a A compound in which the group is a hydroxyl group or a hydrogen atom.
[0018] Next, a method for producing the present compound (including the compound of the present invention) will be described.
[0019] Manufacturing Method A The compound represented by formula (I-A) (hereinafter referred to as compound (I-A)) can be produced by reacting the compound represented by formula (B1) (hereinafter referred to as compound (B1)) and the compound represented by formula (M1) (hereinafter referred to as compound (M1)) in the presence of a palladium catalyst. [In the formula, X 1 represents a chlorine atom, a bromine atom, an iodine atom, or a trifuryloxy group, Met 1 represents B(OH)2,4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, tributylstannyl group, ZnBr, MgBr, or MgCl, and ring A 1 This represents a phenyl group, a 5-6 member aromatic heterocyclic group {the phenyl group and the 5-6 member aromatic heterocyclic group may be substituted with one or more substituents selected from group A}, a C3-C6 alicyclic hydrocarbon group, and a 3-6 member non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3-6 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group B} (wherein ring A 1 In Met 1Or, the atom bonded to the benzene ring shown in compound (I-A) is a carbon atom), other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and 1,2-dimethoxyethane (hereinafter referred to as DME) (hereinafter referred to as ethers); halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); amides such as dimethylformamide (hereinafter referred to as DMF) and N-methylpyrrolidone (hereinafter referred to as NMP) (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles); dimethyl sulfoxide (hereinafter referred to as DMSO), water, and mixtures of two or more of these. Examples of palladium catalysts used in the reaction include palladium(II) acetate and [1,1'-bis(diphenylphosphin)ferrocene]palladium(II) dichloride. In the reaction, compound (M1) is usually used in a ratio of 0.5 to 2 moles and palladium catalyst in a ratio of 0.01 to 0.3 moles per mole of compound (B1). A base may be added to the reaction as needed. Examples of bases that may be used in the reaction as needed 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. When a base is used in the reaction, the base is usually used in a ratio of 1 to 10 moles per mole of compound (B1). The reaction temperature is usually in the range of 0°C to 150°C. The reaction time is typically in the range of 0.1 to 120 hours. After the reaction is complete, compound (I-A) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.Compound (M1) is either publicly known or can be produced according to known methods.
[0020] Manufacturing Method B Compound (I-A) can also be produced 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. [In the formula, the symbols have the same meaning as above (however, ring A) 1 In X 1 (or the atom bonded to the benzene ring shown in compound (I-A) is a carbon atom.) The reaction can be carried out in accordance with manufacturing method A, using compound (M2) instead of compound (B1), and using compound (B2) instead of compound (M1). Compound (M2) is known or can be manufactured in accordance with known methods.
[0021] Manufacturing Method C-1 The compound represented by formula (I-B) (hereinafter referred to as compound (I-B)) can be produced by reacting compound (B1) and the compound represented by formula (M3) (hereinafter referred to as compound (M3)) in the presence of a copper catalyst and a base. [In the ceremony, Z 51 OR 3 , or SR 4The symbols represent the same meaning as above. The reaction is usually carried out in a solvent. Solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, DMSO, water, and mixtures of two or more of these. Copper catalysts used in the reaction include, for example, copper(I) iodide and copper(I) bromide. Bases used in the reaction include, for example, organic bases, alkali metal carbonates, alkali metal bicarbonates, and tripotassium phosphate. Compound (M3) is usually used in a ratio of 0.5 to 2 moles, copper catalyst in a ratio of 0.01 to 0.5 moles, and base in a ratio of 1 to 10 moles per mole of compound (B1). Ligands may be added to the reaction as needed. Ligands that may be used in the reaction as needed include diamines such as N,N'-dimethylethylenediamine and trans-N,N'-dimethylcyclohexane-1,2-diamine (hereinafter referred to as diamines), and amino acid derivatives such as N-methylglycine. When ligands are used in the reaction, the ligand is usually used in a ratio of 0.01 moles to 4.0 moles per mole of compound (B1). The reaction temperature is usually in the range of 0°C to 150°C. The reaction time is usually in the range of 0.1 hours to 120 hours. After the reaction is complete, compound (I-B) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating it. Compound (M3) is either known or can be produced according to known methods.
[0022] Manufacturing Method C-2 The compound represented by formula (I-C) (hereinafter referred to as compound (I-C)) can be produced by reacting compound (B1) and the compound represented by formula (M3-1) (hereinafter referred to as compound (M3-1)) in the presence of a copper catalyst and a base. [In the formula, ring A 10The symbol represents a five-membered aromatic nitrogen-containing heterocycle which may be substituted with one or more substituents selected from group A, or a three- to six-membered non-aromatic nitrogen-containing heterocycle which may be substituted with one or more substituents selected from group B, and the other symbols have the same meaning as above. The reaction can be carried out in accordance with production method C-1, using compound (M3-1) instead of compound (M3). Compound (M3-1) is known or can be produced in accordance with known methods.
[0023] Manufacturing Method D The compound represented by formula (I-D) (hereinafter referred to as compound (I-D)) can be produced by reacting the compound represented by formula (B5) (hereinafter referred to as compound (B5)) with an oxidizing agent, and the compound represented by formula (I-E) (hereinafter referred to as compound (I-E)) can be produced by reacting compound (I-D) with an oxidizing agent. [In the formula, R 51 R 4 or R 8』 represents the same meaning as above, and other symbols have the same meaning as above. First, a method for producing compounds (I-D) from compound (B5) will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of these. Examples of oxidizing agents used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide. When hydrogen peroxide is used as an oxidizing agent, an acid, base, or catalyst may be added as needed. An example of an acid that may be used in the reaction as needed is trifluoroacetic acid. When an acid is used in the reaction, the acid is usually used in a ratio of 0.01 moles to 1 mole per mole of compound (B5). An example of a base that may be used in the reaction as needed is sodium carbonate. When a base is used in the reaction, the base is usually used in a ratio of 0.01 moles to 1 mole per mole of compound (B5). An example of a catalyst that may be used in the reaction as needed is sodium tungstate. When a catalyst is used in the reaction, typically 0.01 to 0.5 moles of catalyst are used per mole of compound (B5). Typically 1 to 1.2 moles of oxidizing agent are used per mole of compound (B5). The reaction temperature is typically in the range of -20°C to 80°C. The reaction time is typically in the range of 0.1 to 12 hours. After the reaction is complete, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is washed with aqueous solutions of reducing agents such as sodium sulfite and sodium thiosulfate, and aqueous solutions of bases such as sodium bicarbonate, as needed. Compounds (I-D) can be obtained by drying and concentrating the organic layer.
[0024] Next, a method for producing compound (I-E) from compound (I-D) is described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of these. Examples of oxidizing agents used in the reaction include mCPBA and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be added as needed. An example of a base that may be used as needed is sodium carbonate. When a base is used in the reaction, it is usually used in a ratio of 0.01 moles to 1 mole of the base per mole of compound (I-D). An example of a catalyst that may be used in the reaction as needed is sodium tungstate. When a catalyst is used in the reaction, it is usually used in a ratio of 0.01 moles to 0.5 moles of the catalyst per mole of compound (I-D). In the reaction, an oxidizing agent is usually used in a ratio of 1 mole to 2 moles per mole of compound (I-D). The reaction temperature is usually in the range of -20°C to 120°C. The reaction time is typically in the range of 0.1 to 12 hours. After the reaction is complete, water is added to the reaction mixture, and it is extracted with an organic solvent. The organic layer is then washed with an aqueous solution of a reducing agent such as sodium sulfite or sodium thiosulfate, and an aqueous solution of a base such as sodium bicarbonate, as needed. By drying and concentrating this organic layer, compound (I-E) can be obtained.
[0025] Furthermore, compound (I-E) can also be produced in a single step by reacting compound (B5) with an oxidizing agent. The reaction can be carried out in accordance with the method for producing compound (I-E) from compound (I-D), using an oxidizing agent in a ratio of typically 2 to 5 moles per mole of compound (B5). Compound (B5) can be produced in accordance with production method C-1.
[0026] Intermediate Production Method A The compound represented by formula (C2) (hereinafter referred to as compound (C2)) can be produced by reacting an organolithium reagent, which is generated by reacting the compound represented by formula (M4) (hereinafter referred to as compound (M4)) and the compound represented by formula (M5) (hereinafter referred to as compound (M5)), with the compound represented by formula (C1) (hereinafter referred to as compound (C1)). [In the formula, X 2 represents a bromine atom or an iodine atom, X 3 represents a butyl group, a sec-butyl group, or a tert-butyl group, and the other symbols have the same meaning as above (however, in A, R shown in compound (C2) 1 A carbon atom substituted with, or X 2 (The atom bonded to it is a carbon atom.) First, a method for producing an organolithium reagent from compound (M4) will be described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, and mixtures of two or more of these. For the reaction, compound (M5) is usually used in a ratio of 0.5 moles to 2 moles per mole of compound (M4). The reaction temperature is usually in the range of -78°C to 150°C. The reaction time is usually in the range of 0.1 hours to 120 hours.
[0027] Next, a method for producing compound (C2) from the organolithium reagent is described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, and mixtures of two or more thereof. In the reaction, compound (C1) is usually used in a ratio of 0.5 moles to 2 moles per mole of the organolithium reagent. The reaction temperature is usually in the range of -78°C to 150°C. The reaction time is usually in the range of 0.1 hours to 120 hours. After the reaction is complete, compound (C2) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, drying the resulting organic layer, and concentrating it. Compound (M4) and compound (C1) are known or can be produced according to known methods. Compound (M5) is a commercially available compound or can be produced according to known methods.
[0028] Intermediate production method B Compound (C2) can also be produced by reacting a Grignard reagent produced by reacting compound (M4) with a compound represented by formula (M6) (hereinafter referred to as compound (M6)) with compound (C1). [In the formula, X 4 represents a chlorine atom or a bromine atom, and other symbols have the same meanings as described above (however, in A, the carbon atom substituted by R 1 shown in compound (C2), or the atom bonded to X 2 is a carbon atom).] The reaction can be carried out according to intermediate production method A by using compound (M6) instead of compound (M5). Compound (M6) is a commercially available compound or can be produced according to a known method.
[0029] Intermediate production method C The compound represented by formula (C3) (hereinafter referred to as compound (C3)) can be produced by reacting compound (B1) with bis(pinacolato)diboron in the presence of a base and a palladium catalyst. [In the formula, the symbols have the same meanings as described above.] The reaction can be carried out according to production method A by using bis(pinacolato)diboron instead of compound (M1).
[0030] Intermediate production method D The compound represented by formula (C4) (hereinafter referred to as compound (C4)) can be produced by reacting compound (M4) with a compound represented by formula (M7) (hereinafter referred to as compound (M7)). [In the formula, the symbols have the same meanings as described above (however, in A, the carbon atom substituted by R 1 shown in compound (C4), or the atom bonded to X 2The atom bonded to it is a carbon atom. The reaction can be carried out in accordance with manufacturing method A, using compound (M4) instead of compound (B1), and using compound (M7) instead of compound (M1). The reaction can also be carried out in accordance with the method described in Angewandte Chemie International Edition, 2020, 59, 22460-22464, etc. Compound (M7) is known or can be manufactured in accordance with known methods.
[0031] Intermediate production method E: The compound represented by formula (C5) (hereinafter referred to as compound (C5)) can be produced by dehydroxylating compound (C2). [In the formula, the symbols have the same meaning as above.] Methods of dehydroxylation include, for example, catalytic hydrogen reduction or reaction with phosphorus tribromide. First, catalytic hydrogen reduction is described. Catalytic hydrogen reduction can be carried out by reacting a compound (C2) with hydrogen in the presence of a solvent and a catalyst. Examples of solvents used in the reaction include alcohols, esters, acetic acid, and mixtures of two or more of these. An example of a catalyst used in the reaction is palladium carbon. The hydrogen pressure in the reaction is usually 1 atmosphere to 5 atmospheres. In the reaction, the catalyst is usually used in a ratio of 0.01 moles to 1 mole per mole of compound (C2). The reaction temperature is usually in the range of 10°C to 50°C. The reaction time is usually in the range of 0.1 hours to 120 hours.
[0032] Next, a method for producing compound (C5) by reaction of compound (C2) with phosphorus tribromide is described. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, and mixtures of two or more of these. In the reaction, phosphorus tribromide is usually used in a ratio of 1 mole to 10 moles per mole of compound (C2). The reaction temperature is usually in the range of 0°C to 150°C. The reaction time is usually in the range of 0.1 hours to 120 hours. After the reaction is complete, water is added to the reaction mixture, and the organic layer is washed with an alkaline aqueous solution such as saturated sodium bicarbonate aqueous solution as needed. Compound (C5) can be obtained by performing post-treatment operations such as drying and concentrating the organic layer.
[0033] Intermediate manufacturing method F Compound (C2) can be manufactured by reacting an organolithium reagent, which is produced by reacting compound (M5) and compound (M8), with the compound represented by formula (M9) (hereinafter referred to as compound (M9)). [In the formula, the symbols have the same meaning as above.] The reaction can be carried out in accordance with intermediate preparation method A, using compound (M8) instead of compound (M4) and compound (M9) instead of compound (C1). Compounds (M8) and (M9) are commercially available compounds or can be prepared in accordance with known methods.
[0034] Intermediate production method G: Compound (C2) can also be produced by reacting a Grignard reagent, which is generated by reacting compound (M8) and compound (M6), with compound (M9). [In the formula, the symbols have the same meaning as above.] The reaction can be carried out in accordance with intermediate preparation method A, using compound (M8) instead of compound (M4), compound (M6) instead of compound (M5), and compound (M9) instead of compound (C1).
[0035] Intermediate Production Method H The compound represented by formula (C6) (hereinafter referred to as compound (C6)) can be produced by reacting compound (C2) and the compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base. [In the formula, X 5 The symbols represent a chlorine atom, a bromine atom, an iodine atom, a mesyloxy group, or a trifuryloxy group, and the other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include nitriles, ethers, hydrocarbons, amides, DMSO, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides), alkali metal carbonates, organic bases, and tripotassium phosphate. 5If the compound (C2) is a bromine atom, an iodine atom, or a trifuryloxy group, the reaction may be carried out with the addition of a metal catalyst and ligand as needed. Examples of metal catalysts that may be used in the reaction include palladium catalysts such as palladium(II) acetate and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride; nickel catalysts such as bis(cyclooctadiene)nickel(O) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride. When a metal catalyst is used in the reaction, the metal catalyst is usually used in a ratio of 0.01 moles to 1 mole per mole of compound (C2). Ligands that may be used in the reaction as needed include triphenylphosphine, xanthophos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When ligands are used in the reaction, the ligand is usually used in a ratio of 0.01 moles to 1 mole per mole of compound (C2). In the reaction, the compound (M10) is usually used in a ratio of 1 mole to 10 moles and the base in a ratio of 1 mole to 10 moles per mole of compound (C2). The reaction temperature is typically in the range of -20°C to 200°C. The reaction time is typically in the range of 0.1 hours to 72 hours. After the reaction is complete, compound (C6) can be obtained by post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating it. Compound (M10) is either known or can be produced according to known methods.
[0036] Intermediate Production Method I The compound represented by formula (C7) (hereinafter referred to as compound (C7)) can be produced by reacting the compound represented by formula (M11) (hereinafter referred to as compound (M11)) and the compound represented by formula (M12) (hereinafter referred to as compound (M12)) in the presence of a base. [In the formula, X 6The symbols represent a mesyloxy group, a trifuryloxy group, a chlorine atom, a bromine atom, or an iodine atom, and the other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, hydrocarbons, amides, DMSO, water, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, organic bases, and tripotassium phosphate. In the reaction, compound (M12) is usually used in a ratio of 1 mole to 10 moles of compound (M11), and base is usually used in a ratio of 1 mole to 10 moles of compound (M11). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 hours to 72 hours. After the reaction is complete, compound (C7) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, drying the organic layer, and concentrating it. Compound (M11) and compound (M12) are either known or can be produced according to known methods.
[0037] The compound of the present invention can be mixed with or used in combination with one or more components selected from the group consisting of (a), (b), (c), and (d) below (hereinafter referred to as "the component"). Mixing or used in combination means using the compound of the present invention and the component simultaneously, separately, or at intervals of time. When the compound of the present invention and the component are used simultaneously, the compound of the present invention and the component may be contained in separate formulations or in a single formulation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of (a), (b), (c), and (d) (i.e., the component), and the compound of the present invention.
[0038] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, multisite inhibitors, string organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncoupling agents, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, This group consists of inhibitors of III and IV, voltage-gated sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chord-sound organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal components. These are described in the IRAC classification based on the mechanism of action.
[0039] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signaling inhibitors, lipid and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., triazole-based DMI fungicides), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-point contact active fungicides, microbial fungicides, and other fungicidal active ingredients. These are described in the FRAC classification based on mechanism of action.
[0040] Group (c) is a group of plant growth regulating components (including mycorrhizal fungi and rhizobia).
[0041] Group (d) is the group of repellent components.
[0042] Examples of combinations of this component and the compounds of the present invention are described below. For example, alanycarb + SX means a combination of alanycarb and SX. The abbreviation SX refers to any one of the compounds of the present invention selected from compound group SX1 to SX77. Furthermore, all of the components described below are known components and can be obtained from commercially available formulations or manufactured by known methods. If the component is a microorganism, it can also be obtained from a microbial depositary. The numbers in parentheses represent CAS RN (registered trademark).
[0043] Combinations of the above group (a) components with the compounds of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus angulatus + SX, Bendiocarb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Bentioflumin + SX, Benzoximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX,Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Bisulflufen + SX, Borax + SX, Boric acid + SX, Broflanilide + SX, Bromopropylate + SX, Buprofezin + SX, Butocarboxim + SX, Butoxycarboxim + SX, Cadusafos + SX, Calcium phosphide + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Cartap hydrochloride + SX, Cartap + SX, Chinomethionate + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, Chloropicrin + SX, Chlorpyrifos + SX, Chlorpyrifos-methyl + SX, Chromafenozide + SX, Clofentezine + SX, Clothianidin + SX, Concanamycin A + SX, Coumaphos + SX, Cryolite + SX,Cyanophos + SX, Cyantraniliprole + SX, Cybenzoxasulfyl + SX, Cyclaniliprole + SX, Cyclobutrifluram + SX, Cycloprothrin + SX, Cycloxaprid + SX, Cyenopyrafen + SX, Cyetpyrafen + SX, Cyflumetofen + SX, Cyfluthrin + SX, Cyhalodiamide + SX, Cyhalothrin + SX, Cyhexatin + SX, Cypermethrin + SX, Cyphenothrin + SX, Cyproflanilide + SX, Cyromazine + SX, Dazomet + SX, Deltamethrin + SX, Demeton-S-methyl + SX, Diafenthiuron + SX, Diazinon + SX, Dichlorvos + SX, Dichloromezotiaz + SX, Dicofol + SX, Diclotophos + 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, Ethoxazole + SX, Artemisia absinthium extract + SX, Azadirachta indica extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract + SX, Urtica dioica extract + SX Mistletoe extract (extract of Viscum album) + SX,Fanflu + SX, Fenamiphos + SX, Fenazaquin + SX, Fenbutatin oxide + SX, Fenitrothion + SX, Fenmezoditiaz + SX, Fenobucarb + SX, Fenoxycarb + SX, Fenpropathrin + SX, Fenpyroximate + SX, Fenthion + SX, Fenvalerate + SX, Fipronil + SX, Flometoquin + SX, Flonicamid + SX, Fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flucythrinate + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flumetnicam + SX, flupentiofenox + SX, Flupyradifurone + SX, Flupyrimin + SX, Flupyroxystrobin + SX, Fluralaner + SX, Fluvalinate + SX,Fluxametamide + SX, Formetanate + SX, Fosthiazate + SX, Furamethrin + SX, Furathiocarb + SX, Gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, Halfenprox + SX, Halofenozide + SX, Heptafluthrin + SX, Heptenophos + SX, Hexaflumuron + SX, Hexythiazox + SX, Potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoflualanam + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate salicylate) + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappatefluthrin + SX,Kappa-bifenthrin + SX, Kinoprene + SX, Lambda-cyhalothrin + SX, Ledprona + SX, Lenoremycin + SX, Lepimectin + SX, Lime sulfur + SX, Lotilaner + SX, Lufenuron + SX, Machine oil + SX, Malathion + SX, Mecarbam + SX, Meperfluthrin + SX, Metaflumizone + SX, Metam + SX, Methamidophos + SX, Methidathion + SX, Methiocarb + SX, Methomyl + SX, Methoprene + SX, Methoxychlor + SX, Methoxyfenozide + SX, Methyl bromide + SX, Metofluthrin + SX, Metolcarb + SX, Methoxadiazone + SX, Mevinphos + SX, Milbemectin + SX, Milbemycin oxime + SX, Mivorilaner + SX, Modoflaner + SX, Momfluorothrin + SX, Monocrotophos + SX, Moxidectin + SX, Naled + SX, Nicofluprole + SX, Nicotine + SX,Nicotine sulfate + SX, nitenpyram + SX, novaluron + SX, nobiflumulon + SX, oil of the seeds of Chenopodium anthelminticum + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pioxaniliprole + SX, piperflanilide + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + SX, prothiofos + SX, Pyflubumide + SX, Pymetrozine + SX, Pyraclofos + SX,Pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfoxamyl + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX,Tebufenozide + SX, Tebufenpyrad + SX, Tebupirimfos + SX, Teflubenzuron + SX, Tefluthrin + SX, Temephos + SX, Terbufos + SX, Terpene constituents of the extract of chenopodium ambrosioides near ambrosioides + SX, Tetrachlorantraniliprole + SX, Tetrachlorvinphos + SX, Tetradifon + SX, Tetramethrin + SX, Tetramethylfluthrin + SX, Tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-monosodium + SX, tiapyrachlor + SX, tigolaner + SX, tiorantraniliprole + SX, tioxazafen + SX, Tolfenpyrad + SX, Tralomethrin + SX, Transfluthrin + SX,Triazamate + SX, Triazophos + SX, Trichlorfon + SX, Trifluenfuronate + SX, Triflumezopyrim + SX, Triflumuron + SX, Trimethacarb + SX, Trioxyflanilide + SX, Tyclopyrazoflor + SX, Umifoxolaner + SX, Vadescana + SX, Vamidothion + SX, Wood extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX,N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methanesulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, (S)-2-chloro-N-(3-ethylpentan-2-yl)furan-3-carboxamide + SX, Cry1Ab protein from Bacillus thuringiensis + SX, Cry1Ac protein from Bacillus thuringiensis + SX, Cry1Fa protein from Bacillus thuringiensis + SX, Cry1A.105 protein from Bacillus thuringiensis + SX, Cry2Ab protein from Bacillus thuringiensis SX, Bacillus thuringiensis Vip3A protein + SX, Bacillus thuringiensis mCry3A protein + SX, Bacillus thuringiensis Cry3Ab protein + SX, Bacillus thuringiensis Cry3Ab protein + SX, Bacillus thuringiensis Cry3Bb protein + SX, Bacillus thuringiensis Cry34Ab1 / Cry35Ab1 protein + SX,Adoxophyes orana GV (granulovirus) strain BV-0001 + SX, Anticarsia gemmatalis MNPV (multiple nucleocapsid nucleopolyhedrovirus) + SX, Autographa californica MNPV + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella GV strain V22 + SX, Cryptophlebia leucotreta GV + SX, Dendrolimus punctatus cytoplasmic polyhedron virus + SX, Helicoverpa armigera NPV (nucleopolyhedrovirus) strain BV-0003 + SX, Helicoverpa zea NPV + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX, Mamestra configurata NPV + SX, Neodiprion abietis NPV + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer NPV + SX, Nosema locustae + SX,Orgyia pseudotsugata NPV + SX, Pieris rapae GV + SX, Plodia interpunctella GV + SX, Spodoptera exigua MNPV + SX, Spodoptera littoralis MNPV + SX, Spodoptera litura NPV + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX,Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX,Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinogensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dactylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX,Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。,
[0044] Combinations of the main component from group (b) above with the compounds of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, Benthiavalicarb-isopropyl + SX, Benzovindiflupyr + SX, Bifemetstrobin + SX, Binapacryl + SX, Biphenyl + SX, Bitertanol + SX, Bixafen + SX, Blastoicidin-S + SX, Bordeaux mixture + SX, Boscalid + SX, Bromothalonil + SX, Bromuconazole + SX, Bupirimate + SX, Captafol + SX, Captan + SX, Carbendazim + SX, Carboxin + SX, Carpropamid + SX, Chinomethionate + SX, Chitin + SX, Chloroinconazide + SX,Chloroneb + SX, chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, basic copper chloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, Diclobentiazox + SX, Dichlofluanid + SX, Diclocymet + SX, Diclomezine + SX, Dichloran + SX, Dietofencarb + SX, Difenoconazole + SX, Diflumetorim + SX, Dimethachlone + SX, Dimethirimol + SX, Dimethomorph + SX, Dimoxystrobin + SX, Diniconazole + SX, Diniconazole-M + SX, Dinocap + SX, Dipotassium hydrogen phosphite + SX, Dipymetitrone + SX, Dithianon + SX,Dodecylbenzenesulfonic acid bisethylenediamine copper(II) complex salt + SX, Dodemorph + SX, Dodine + SX, Edifenphos + SX, Enoxastrobin + SX, Epoxiconazole + SX, Etaconazole + SX, Ethaboxam + SX, Ethirimol + SX, Etridiazole + SX, Garlic extract (Allium sativum) + SX, Extract of the cotyledons of lupine plantlets ("BLAD") + SX, Horsetail extract (Equisetum arvense) + SX, Tea tree extract (extract of Melaleuca alternifolia) + SX, Japanese knotweed extract (extract of Reynoutria sachalinensis) + SX, Nasturtium extract (extract of Tropaeolum majus) + SX, Famoxadone + SX, Fenamidone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenbuconazole + SX, Feneptamidoquin + SX, Fenfuram + SX, Fenhexamide + SX, Fenopyramid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamide + SX,Fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, fentin acetate + SX, fentin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, fluquinometoate + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, Flutriafol + SX, Fluxapyroxad + SX, Folpet + SX, Fosetyl + SX,Fosetyl-aluminium + SX, Fuberidazole + SX, Furalaxyl + SX, Furametpyr + SX, Galquin + SX, Guazatine + SX, Hexaconazole + SX, Hymexazole + SX, Imazalil + SX, Imibenconazole + SX, Iminoctadine + SX, Iminoctadine triacetate + SX, Inpyrfluxam + SX, Iodocarb + SX, Ipconazole + SX, Ipfentrifluconazole + SX, Ipflufenoquin + SX, Iprobenfos + SX, Iprodione + SX, Iprovalicarb + SX, Isofetamide + SX, Isoflucypram + SX, Isoprothiolane + SX, Isopyrazam + SX, Isothianil + SX, Kasugamycin + SX, Kresoxim-methyl + SX, Laminarin + SX, Leaves and bark of Quercus + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamid + SX, Maneb + SX, Mefentrifluconazole + SX, Mepanipyrim + SX,Mepronil + SX, Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Metarylpicoxamide + SX, Metconazole + SX, Methasulfocarb + SX, Methylam + SX, Metominostrobin + SX, Metrafenone + SX, Methyltetraprole + SX, Myclobutanil + SX, Naftifine + SX, Nuarimol + SX, Octilinone + SX, Ofurace + SX, Orysastrobin + SX, Oxadixyl + SX, Oxathiapiprolin + SX, Oxine-copper + SX, Oxolinic acid + SX, Oxpoconazole + SX, Oxpoconazole fumarate + SX, Oxcarboxin + SX, Oxtetracycline + SX, Pefurazoate + SX, Penconazole + SX, Pencycuron + SX, Penflufen + SX, Penthiopyrad + SX, Phenamacril + SX, Phosphorous acid + SX, Phthalide + SX, Picarbutrazox + SX, Picoxystrobin + SX,Piperalin + SX, Polyoxins + SX, Potassium hydrogencarbonate + SX, Potassium dihydrogenphosphite + SX, Probenazole + SX, Prochloraz + SX, Procymidone + SX, Propamidine + SX, Propamocarb + SX, Propiconazole + SX, Propineb + SX, Proquinazid + SX, Prothiocarb + SX, Prothioconazole + SX, Pydiflumetofen + SX, Pyraclostrobin + SX, Pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract + SX, Quinconazole + SX, Quinofumelin + SX, Quinoxyfen + SX, Quintozene + SX,Quinoa saponins (Saponins of Chenopodium quinoa) + SX, Seboctylamine + SX, Sedaxane + SX, Silthiofam + SX, Simeconazole + SX, Sodium hydrogencarbonate + SX, Spiroxamine + SX, Streptomycin + SX, Sulfur + SX, Tebuconazole + SX, Tebufloquin + SX, Teclofthalam + SX, Tecnazene + SX, Terbinafine + SX, Tetraconazole + SX, Thiabendazole + SX, tifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, Tridemorph + SX, Trifloxystrobin + SX, Triflumizole + SX, Triforine + SX,トリチコナゾール(triticonazole) + SX, バリダマイシン(validamycin) + SX, バリフェナレート(valifenalate) + SX, ビンクロゾリン(vinclozolin) + SX, マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(zoxamide) + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-d ichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX,N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, [4-(difluoromethoxy)phenyl]methyl 4-[(N-ethyl-N-methylamino)methylidene]amino-2,5-dimethylbenzoate + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX,3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX,4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX,1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxolan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-met hylthiazole-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX,5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, methyl ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, N-[2-(pyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(6-cyanopyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[(2S)-2-(6-chloro-4-methoxypyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[(2R)-2-(6-chloro-4-methoxypyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-(2-{6-[(1E)-(methoxyimino)ethyl]pyridin-2-yl}-2-(1-methylpyrazol-4-yl)propyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(5-methylpyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-dichlorophenyl)isoxazole-3-carboxamide + SX, methyl 6-(2-{[5-(2,4-difluorophenyl)isoxazole-3-carbonyl]amino}-1-methyl-1-(1-methylpyrazol-4-yl)ethyl)pyridine-3-carboxylate + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)isoxazole-3-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-3-(2,4-difluorophenyl)-1,2,4-oxadiazole-5-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(5-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-cyanopyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,6-difluoropyridin-3-yl)-1,3,4-thiadiazole-2-carboxamide + SX, Agrobacterium radiobactor strain K1026 + 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 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX,Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX,Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX,Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX,Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,
[0045] Combinations of the main component from group (c) above with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloride + SX, cloprop + SX, cyanamide + SX, Cyclanilide + SX,Daminozide + SX, Decan-1-ol + SX, Dichlorprop + SX, Dikegulac + SX, Dimethipin + SX, Diquat + SX, Ethephon + SX, Ethychlozate + SX, Flumetralin + SX, Flurprimidol + SX, Forchlorfenuron + SX, Formononetin + SX, Gibberellin A + SX, Gibberellin A3 + SX, Inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat-chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione-calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintofen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, Thidiazuron + SX, Tripenthenol + SX, Tribufos + SX, Trinexapac-ethyl + SX,Uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate methyl + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX,Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX. ,
[0046] Combinations of the above group (d) components with the compounds of the present invention: anthraquinone + SX, DEET + SX, icaridin + SX.
[0047] The ratio of the compound of the present invention to the component of this invention is not particularly limited, but examples of weight ratios (compound of the present invention:component of this invention) include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc.
[0048] This compound, the compound of the present invention, or composition A can control plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, phytomyxea, and bacteria. Examples of fungi include Ascomycota, Basidiomycota, Blastocoladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specifically, examples include the following. The names in parentheses indicate the scientific names of the plant pathogenic microorganisms that cause each disease.
[0049] Rice diseases: blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellowing and withering disease (Sclerophthora macrospora), false blast and ear blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae), suspected sheath blight (red sclerotium pathogen (Waitea circinata), brown sclerotium pathogen (Ceratobasidium setariae), brown sheath blight pathogen (Thanatephorus cucumeris)), false smut (Ustilaginoidea virens), black kernel smut (Tilletia horrida, Tilletia barclayana);Wheat diseases: Powdery mildew (Blumeria graminis), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Red rust (Puccinia recondita), Red snow mold (Microdochium nivale, Microdochium majus), Snow mold (Typhula incarnata, Typhula ishikariensis), Snow mold (Sclerotinia borealis), Brown snow mold (Pythium spp.), Naked smut (Ustilago tritici), Smut (Tilletia caries, Tilletia controversa), Eye spot disease (Pseudocercosporella herpotrichoides), Leaf blight (Septoria tritici), rotten blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), seedling damping off caused by Rhizoctonia fungi (Rhizoctonia solani), damping off (Gaeumannomyces graminis), rice blast (Pyricularia graminis-tritici);Barley diseases: powdery mildew (Blumeria graminis), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, yellow rust (Puccinia striiformis), black rust (Puccinia graminis), small rust (Puccinia hordei), bare smut (Ustilago nuda), cloudy smut (Rhynchosporium secalis), net-like spot (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf spot (Pyrenophora graminea), Ramularia leaf spot (Ramularia collo-cygni), seedling blight caused by Rhizoctonia fungi (Rhizoctonia solani); maize diseases: rust (Puccinia sorghi), southern rust (Puccinia Polysora, sooty mold (Setosphaeria turcica), tropical rust (Physopella zeae), sesame leaf spot (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria maydis, Diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), Stoke's disease (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis), Physoderma disease (Physoderma maydis), tar spot disease (Phyllachora maydis);Cotton diseases: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola); coffee diseases: coffee rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola); rapeseed diseases: sclerotinia sclerotiorum, black spot (Alternaria brassicae), root rot (Phoma lingam), light leaf spot (Pyrenopeziza brassicae); sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea); sunflower diseases: rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger, white mold (Geotrichum candidum var. citri-aurantii), sooty mold (Cladosporium cladosporioides);Apple diseases: Monilinia mali, canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), apple leaf spot (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring spot (Botryosphaeria berengeriana), late blight (Phytophtora cactorum), cedar-apple rust (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae); Pear diseases: Black spot (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), cedar-apple rust (Gymnosporangium haraeanum); Peach diseases: Gray mold (Monilinia fructicola), black spot (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), leaf curl (Taphrina deformans), powdery mildew (Podosphaera leucotricha); Grape diseases: Black rot (Elsinoe ampelina), late blight (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Neophysopella sp.), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), brown spot (Pseudocercospora vitis), white rot (Coniella castaneicola); Persimmon diseases: Anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf spot (Cercospora kaki, Mycosphaerella Nawae, powdery mildew (Phyllactinia kakicola);Fig diseases: rust (Phakopsora nishidana); Cucurbit diseases: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), vine wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora capsici), seedling blight (Pythium sp.), Phomopsis root rot (Phomopsis sp.); Tomato diseases: ring spot (Alternaria solani), leaf mold (Cladosporium fulvum), sooty mold (Pseudocercospora fuligena), late blight (Phytophthora infestans), powdery mildew (Leveillula taurica); Eggplant diseases: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), black blight (Corynespora melongenae), sooty mold (Mycovellosiella nattrassii), brown spot (Thanatephorus cucumeris); Brassicaceae vegetable diseases: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida), black sooty mold (Alternaria brassicola); Onion diseases: rust (Puccinia allii), black spot (Alternaria porri), black rot (Sclerotium cepivorum), small sclerotium rot (Botrytis squamosa), leaf blight (Stemphylium) vesicarium, Stempphylium botryosum), white silk disease (Sclerotium rolfsii), white spot leaf blight (Botrytis squamosa);Soybean diseases: Purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf blight (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia rot (Sclerotinia sclerotiorum), powdery mildew (Microsphaera diffusa), stem blight (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death disease (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe / Phomopsis Soybean pod abnormalities caused by various causative fungi (Diaporthe longicolla, Diaporthe phaseolorum, Phomopsis longicolla): pod anomalies; Bean diseases: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), horn spot disease (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani); Peanut diseases: Black spot disease (Cercospora personata), brown spot disease (Cercospora arachidicola), white mold disease (Sclerotium rolfsii), black root rot (Calonectria ilicicola); Pea diseases: Powdery mildew (Erysiphe pisi), root rot (Fusarium solani);Potato diseases: Late blight (Alternaria solani), late blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. sp. subterranea), Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens, dry rot (Fusarium solani), crown gall (Synchytrium endobioticum); Strawberry diseases: Powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum); Tea diseases: Net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), ring spot (Pestalotiopsis) Diseases of tobacco plants: red rust (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), blight (Phytophthora nicotianae); Diseases of sugar beets: brown spot (Cercospora beticola), leaf blight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides), rust (Uromyces betae); Diseases of roses: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); Diseases of chrysanthemums: brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana); Onion diseases: White spot leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotinia rot (Botrytis squamosa);Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia sclerotiorum, black rot (Sclerotium cepivorum), white mold (Sclerotium rolfsii), seedling blight (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum); diseases of radishes: black spot (Alternaria brassicicola); diseases of sweet potatoes: vine wilt (Fusarium oxysporum f. sp. batatas), basal rot (Diaporthe destruens), black spot (Ceratocystis fimbriata); diseases of turfgrass: dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), red blight (Pythium aphanidermatum), anthracnose (Colletotrichum). caudatum); Banana diseases: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola); Lentil diseases: Ascochyta disease (Ascochyta lentis); Chickpea diseases: Ascochyta disease (Ascochyta rabiei); Bell pepper diseases: Anthracnose (Colletotrichum scovillei), powdery mildew (Leveillula taurica), white mold (Sclerotium rolfsii); Mango diseases: Anthracnose (Colletotrichum acutatum); Cacao diseases: Witches' broom disease (Moniliophthora perniciosa), Frosty pod rot (Moniliophthora roreri); Pecan diseases: Black spot disease (Venturia effusa); Lychee diseases: Downy mildew (Peronophythora litchii), Anthracnose (Colletotrichum siemense); Fruit tree diseases: White root rot (Rosellinia necatrix), Purple root rot (Helicobasidium mompa);Diseases of fruits such as apples and pears after harvest: Mucor piriformis; seed diseases or diseases of the early growth stage caused by genera such as Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia; Viral diseases: Big vein disease of lettuce transmitted by Olpidium brassicae, viral diseases of various crops transmitted by the genus Polymyxa (e.g., Polymyxa betae and Polymyxa graminis); Diseases caused by bacteria: Bacterial blight of rice (Burkholderia plantarii), blotch of rice (Pantoea ananatis), bacterial leaf blight of rice (Xanthomonas oryzae pv. Oryzae, bacterial leaf spot of cucumber (Pseudomonas syringae pv. Lachrymans), bacterial wilt of eggplant (Ralstonia solanacearum), citrus canker (Xanthomonas citri), soft rot of Chinese cabbage (Erwinia carotovora), potato scab (Streptomyces scabiei), potato blackfoot (Pectobacterium carotovorum, Dickeya sp.), bacterial spot of peach (Pseudomona syringae, Erwinia nigrifluens, Xanthomonas campestris), citrus canker of plum (Pseudomonas syringae pv. Morsprunorum, Erwinia sp.), Goss's wilt of corn (Clavibacter michiganensis), piercing disease of grapes, olives, peaches, etc. (Xylella Agrobacterium tumefaciens (also known as fastidiosa), a crown gall disease affecting rose family plants such as apples, peaches, and cherries.
[0050] Soybean rust fungus with the F129L amino acid substitution in the mitochondrial cytochrome b protein is a soybean rust fungus (scientific name: Phakopsora pachyrhizi) that has a mutation in the mitochondrial cytochrome b gene that codes for the mitochondrial cytochrome protein, and as a result of this mutation, the F129L amino acid substitution occurs, making it resistant to the QoI fungicide.
[0051] The plant disease control method of the present invention is carried out by treating a plant or the soil in which the plant is cultivated with an effective amount of the present compound, the compound of the present invention, or composition A. Examples of treatment methods include treatment of stems and leaves, soil treatment, and seed treatment.
[0052] The present compound, the compound of the present invention, or composition A is typically used by mixing an inert carrier such as a solid carrier or liquid carrier with a surfactant, and adding formulation aids such as binders, dispersants, and stabilizers as needed, to formulate it into aqueous suspensions, oily suspensions, oils, emulsions, microemulsions, microcapsules, wettable powders, wettable granules, powders, granules, etc. It is not limited to these formulations, but can also be used in formulations described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain the present compound, the compound of the present invention, or composition A in an amount of 0.0001% to 99% by weight.
[0053] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powders and granules of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).
[0054] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).
[0055] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).
[0056] Other pharmaceutical additives include, for example, binders, dispersants, colorants, and stabilizers. Specifically, examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, and dibutylhydroxytoluene.
[0057] Furthermore, adjuvants can be used as components to enhance or assist the efficacy of this compound, the compound of the present invention, or composition A. Specifically, these include AgriDex®, Induce®, Gramin S®, Genamin T 200BM®, Silwet L77®, Nimbus®, Assist®, Aureo®, Iharol Gold®, BreakThru®, Sundance II®, Lutensol A8®, NP-7®, Triton®, Nufilm®, Emulgator NP7®, Emulad®, TRITON X 45®, AGRAL 90®, AGROTIN®, ARPON®, EnSpray N®, BANOLE®, Ochima®, Agris®, AMS (Ammonium Sulfate), UAN (Urea Ammonium) Examples include Nitrate (ammonium urea nitrate), AdGreen (registered trademark), Mees (trademark), Rumba (registered trademark), Strides (registered trademark), Partner, Orix (registered trademark), and Penetrator.
[0058] In the present invention, "plant" includes the whole plant and specific parts of the plant. Examples of specific parts of a plant include stems and leaves, flowers, spikes, fruits, trunks, branches, canopies, seeds, vegetative reproductive organs, and seedlings.
[0059] Vegetative reproductive organs refer to parts of a plant, such as roots, stems, and leaves, that have the ability to grow when separated from the main plant and placed in the soil. Examples of vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms (or solid bulbs), rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. Stolons are sometimes called runners, and cane cuttings are also called bulbils, and are divided into broad buds and bulbils. Vines refer to shoots (a general term for leaves and stems) of plants such as sweet potatoes and yams. Bulbs, corms, tubers, rhizomes, cane cuttings, propagules, or tubers are collectively called bulbs. Potato cultivation begins with planting tubers in the soil, and the tubers used are generally called seed potatoes.
[0060] Seedlings include seedlings and saplings.
[0061] A method for controlling plant diseases by applying an effective amount of this compound, the compound of the present invention, or composition A to the soil includes, for example, applying an effective amount of this compound, the compound of the present invention, or composition A to the soil before or after planting plants. More specifically, for example, planting hole treatment (spraying in planting holes, mixing in planting hole treatment soil), base treatment (spraying around the base of the plant, mixing around the base of the plant, drenching around the base of the plant, base treatment in the latter half of the seedling stage), furrow treatment (spraying in planting furrows, mixing in planting furrow soil), furrow treatment (spraying in furrows, mixing in furrow soil, spraying in furrows during the growing season), furrow treatment at sowing (spraying in furrows at sowing, mixing in furrow soil at sowing), overall treatment (spraying in all areas of soil, mixing in all areas of soil), side-dressing treatment, water surface treatment (application to the water surface, application to the water surface after flooding), other soil application treatments (foliar application of granular fertilizer during the growing season, application under the tree canopy or around the main trunk, application to the soil surface, mixing to the soil surface, spraying in planting holes, application to the soil surface on ridges, application between plants), and so on. Other drenching treatments include soil drenching, seedling stage drenching, chemical injection treatment, drenching at the base of the plant, chemical drip irrigation, and chemigation. Seedling tray treatments include seedling tray spraying, seedling tray drenching, and seedling tray watering. Seedling tray treatments include seedling tray spraying, seedling tray drenching, and seedling tray watering. Seedbed treatments include seedbed spraying, seedbed drenching, watered seedbed spraying, and seedling soaking. Seedbed soil mixing treatments include seedbed soil mixing, seedbed soil mixing before sowing, spraying before covering with soil at sowing, spraying after covering with soil at sowing, and soil mixing with covering soil. Other treatments include growing soil mixing, tilling, topsoil mixing, soil mixing at the rainwater drainage area, planting location treatment, granular flower cluster spraying, and paste fertilizer mixing.
[0062] Seed treatments include, for example, treatment of seeds or vegetative reproductive organs with the present compound, the compound of the present invention, or composition A. More specifically, these include, for example, a spray treatment in which a suspension of the present compound, the compound of the present invention, or composition A is sprayed in a mist onto the surface of the seed or vegetative reproductive organ; a coating treatment in which the present compound, the compound of the present invention, or composition A is applied to the seed or vegetative reproductive organ; an immersion treatment in which the seed or vegetative reproductive organ is immersed in a solution of the present compound, the compound of the present invention, or composition A for a certain period of time; and a method of coating the seed or vegetative reproductive organ with a carrier containing the present compound, the compound of the present invention, or composition A (film coating treatment, pellet coating treatment, etc.). Seed potatoes are a particularly good example of the vegetative reproductive organs mentioned above. In the present invention, a seed or vegetative reproductive organ holding the present compound, the compound of the present invention, or composition A means a seed or vegetative reproductive organ in which the present compound, the compound of the present invention, or composition A is attached to its surface. The above seed or vegetative reproductive organ holding the present compound, the compound of the present invention, or composition A may have other materials attached to it before or after the present compound, the compound of the present invention, or composition A is attached to it. Furthermore, when composition A adheres to the surface of a seed or vegetative reproductive organ in a layer, the layer consists of one or more layers. If it consists of multiple layers, each layer either contains one or more active ingredients, or consists of a layer containing one or more active ingredients and a layer not containing any active ingredients. Seeds or vegetative reproductive organs holding this compound, the compound of the present invention, or composition A can be obtained, for example, by applying a formulation containing this compound, the compound of the present invention, or composition A to the seed or vegetative reproductive organ using the seed treatment method described above.
[0063] The application rate of this compound, the compound of the present invention, or composition A varies depending on weather conditions, formulation form, application timing, application method, application location, target disease, target crop, etc. However, in the case of foliar treatment or soil treatment, the application rate is 1000 m² of plant cultivation area. 2The amount is usually 1g to 500g per unit. In the case of seed treatment, the amount of this compound, the compound of the present invention, or composition A per 1kg of seeds is usually 0.001g to 100g. When this compound, the compound of the present invention, or composition A is formulated as an emulsion, wettable powder, flowable formulation, etc., it is usually diluted with water to an active ingredient concentration of 0.01ppm to 10000ppm before application, while powders, granules, etc., are usually applied as is.
[0064] This compound, the compound of the present invention, or composition A can be used as a control agent for plant diseases in agricultural land such as fields, paddy fields, lawns, and orchards. Examples of plants include the following:
[0065] Corn (Horsetail, hard-grain, soft-grain, popping, glutinous, sweet, field corn), rice (long-grain, short-grain, medium-grain, Japonica, tropical Japonica, Indica, Javanica, paddy rice, upland rice, floating rice, direct seeding, transplanting, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each with winter wheat type and spring wheat type), barley (two-row barley (= malting barley), six-row barley, hulless barley, glutinous barley, each with winter barley type and spring barley type), rye (winter rye type, spring rye) (Types), Triticare (winter Triticare type, spring Triticare type), oats (winter oat type, spring oat type), sorghum, cotton (Upland variety, Pima variety), soybeans (full-seed harvest varieties, edamame varieties, green-harvested varieties, each with infinite growth type, finite growth type, and semi-finite growth type), peanuts, potatoes (tetraploid, diploid, true seed varieties), buckwheat, sugar beets (for sugar production, for animal feed, root vegetables, leafy vegetables, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflowers (for oil extraction, food, ornamental), sugarcane, tobacco, tea plants, mulberry, eggplant Vegetables from the genus Aceraceae (eggplant, tomato, bell pepper, chili pepper, etc.), Cucurbitaceae (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae (leek, onion, garlic, asparagus, etc.), Apiaceae (carrot, parsley, celery, angelica tree, etc.), Chenopodiaceae (spinach, Swiss chard, etc.), Lamiaceae (perilla, mint, basil, etc.), strawberry Sweet potatoes, Japanese yams, taro, pomelo (apples, European pears, Japanese pears, Chinese pears, quince, marzipan, etc.), drupes (peaches, plums, nectarines, apricots, cherries, prunes, etc.), citrus fruits (Unshu mandarins, oranges, lemons, limes, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates,Coconut palms, ornamental plants, forest plants, grasses, and pasture grasses.
[0066] The plants listed above are not limited to any commonly cultivated varieties. These include plants that can be produced through natural cross-pollination, plants that can arise from spontaneous mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants conferred with resistance to HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutol, ALS (acetolactate synthase) inhibitors such as imazetapyr and thifensulfuron-methyl, EPSP (5-enolpyruvirshikimate-3-phosphate synthase) inhibitors, glutamine synthase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or herbicides such as dicamba; plants capable of synthesizing selective toxins known from the Bacillus genus, such as Bacillus thuringiensis; and plants that can be conferred with specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) within the target harmful insect.
[0067] The present invention will be described in more detail below with reference manufacturing examples, production examples, formulation examples, and test examples, but the present invention is not limited to these examples.
[0068] In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, iPr represents an isopropyl group, cPr represents a cyclopropyl group, Bu represents a butyl group, cBu represents a cyclobutyl group, iBu represents an isobutyl group, sBu represents a sec-butyl group, tBu represents a tert-butyl group, Ph represents a phenyl group, cPen represents a cyclopentyl group, and cHex represents a cyclohexyl group. If these groups have substituents, the substituents are indicated before the symbols of these groups along with their substitution positions. For example, 4-OMe-Ph represents a 4-methoxyphenyl group, and 3,5-Me2-Ph represents a 3,5-dimethylphenyl group.
[0069] When the physical properties of a compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LC / MS), the measured molecular ion value [M + H] + or [M-H] - The retention time (hereinafter referred to as RT) is also noted. The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows: [LC conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (manufactured by the Chemicals Evaluation and Research Institute) UV measurement wavelength: 254 nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Pump: LC-20AD (manufactured by Shimadzu Corporation) 2 units (high pressure gradient) Gradient conditions: The solution is delivered with the concentration gradient described in [Table LC1].
[0070]
[0071] [MS conditions] Detector: LCMS-2020 (manufactured by Shimadzu Corporation) Ionization method: DUIS (ESI, APCI)
[0072] First, we will show an example of the preparation of the compound (including the compound of the present invention). Preparation Example 1 A mixture of 0.18 g of phenylboronic acid, 0.30 g of 2-(4-bromobenzyl)-2H-1,2,3-triazole, 0.03 g of {1,1'-bis(diphenylphosphino)ferrocene}dichloropalladium(II), 0.54 g of tripotassium phosphate, 4.2 mL of DME, and 0.4 mL of water was stirred under reflux for 3 hours. After cooling to room temperature, water was added to the resulting mixture and extracted with ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 0.25 g of compound 1, shown by the following formula. This compound 1: 1 H-NMR (CDCl3) δ: 7.65 (2H, s), 7.59-7.54 (4H, m), 7.45-7.32 (5H, m), 5.66 (2H, s).
[0073] Manufacturing Example 1-1 The compound manufactured according to Manufacturing Example 1 and its physical properties are shown below. Formula (IA-1) In the compound shown (hereinafter referred to as compound (IA-1)), J 1P J 2P J 3P J 4P G 1p G 2p G 3p G 4p , and G 5p A compound whose combination is one of the combinations listed in [Table A-1].
[0074] This compound 2: 1 H-NMR (CDCl3) δ: 7.65 (2H, s), 7.56-7.51 (2H, m), 7.43-7.37 (3H, m), 7.35-7.28 (1H, m), 7.22-7.11 (2H, m), 5.66 (2H, s). Compound 3: 1 H-NMR (CDCl3) δ: 7.65 (2H, s), 7.50-7.46 (2H, m), 7.41-7.33 (3H, m), 6.97-6.86 (2H, m), 5.66 (2H, s). Compound 4: 1 H-NMR (CDCl3) δ: 8.83 (1H, s), 8.60 (1H, d), 7.84 (1H, d), 7.66 (2H, s), 7.60-7.54 (2H, m), 7.45-7.40 (2H, m), 7.36 (1H, dd), 5.67 (2H, s). Compound 5: 1 H-NMR (CDCl3) δ: 8.40 (1H, dd), 7.67 (2H, s), 7.64 (1H, dd), 7.46-7.42 (2H, m), 7.41-7.37 (2H, m), 7.31 (1H, dd), 5.69 (2H, s). Compound 6: 1 H-NMR (CDCl3) δ: 8.40-8.38 (1H, m), 7.96-7.91 (1H, m), 7.66 (2H, s), 7.54-7.50 (2H, m), 7.44-7.40 (2H, m), 7.02-6.99 (1H, m), 5.67 (2H, s). Compound 7: 1¹H-NMR (CDCl₃) δ: 7.57–7.54 (4H, m), 7.43–7.34 (5H, m), 4.08 (2H, s), 2.56 (3H, s). Compound 8: 1 ¹H-NMR (CDCl₃) δ: 7.53–7.50 (2H, m), 7.43–7.38 (3H, m), 7.33–7.28 (1H, m), 7.21–7.11 (2H, m), 4.09 (2H, s), 2.56 (3H, s). Compound 9: 1 ¹H-NMR (CDCl₃) δ: 7.50–7.44 (2H, m), 7.42–7.34 (3H, m), 6.96–6.87 (2H, m), 4.09 (2H, s), 2.56 (3H, s). Compound 10: 1 ¹H-NMR (CDCl₃) δ: 7.99–7.90 (¹H, m), 7.52–7.47 (²H, m), 7.45–7.41 (²H, m), 6.92 (¹H, dd), 4.10 (²H, s), 2.56 (³H, s). Compound 11: 1 ¹H-NMR (CDCl₃) δ: 8.39 (¹H, dd), 7.65 (¹H, dd), 7.45–7.41 (4H, m), 7.31 (¹H, dd), 4.11 (2H, s), 2.57 (3H, s). Compound 12: 1 ¹H-NMR (CDCl₃) δ: 8.20–8.18 (¹H, m), 7.88–7.83 (¹H, m), 7.57–7.51 (²H, m), 7.46–7.40 (²H, m), 7.29–7.25 (¹H, m), 4.10 (²H, s), 2.56 (³H, s). Compound 13: 1 ¹H-NMR (CDCl₃) δ: 8.53 (¹H, s), 7.59–7.56 (⁴H, m), 7.46–7.42 (⁴H, m), 7.38–7.34 (¹H, m), 5.84 (⁴H, s). Compound 14: 1H-NMR (CDCl3) δ: 8.53 (1H, s), 7.58-7.55 (2H, m), 7.46-7.45 (2H, m), 7.42-7.38 (1H, m), 7.36-7.30 (1H, m), 7.23-7.12 (2H, m), 5.85 (2H, s). Compound 15: 1 H-NMR (CDCl3) δ: 8.54 (1H, s), 7.96-7.92 (1H, m), 7.56-7.52 (2H, m), 7.49-7.47 (2H, m), 6.93 (1H, dd), 5.86 (2H, s).
[0075] Formula (IA-2) In the compound represented by (hereinafter referred to as compound (IA-2)), R 1P , R 2P J 5P J 6P J 7P J 8P G 6p G 7p G 8p G 9p , and G 10p A compound whose combination is one of the combinations listed in [Table A-2].
[0076] This compound 16: 1 H-NMR (CDCl3) δ: 8.59 (1H, d), 8.19-8.18 (1H, m), 7.86-7.84 (1H, m), 7.67-7.65 (1H, m), 7.52 (4H, dd), 7.25-7.20 (3H, m), 5.81 (1H, d), 5.31 (1H, d).
[0077] Preparation Example 2 A mixture of 0.57 g of iodine, 0.57 g of triphenylphosphine, 0.19 g and 0.52 g of imidazole (compound 16), and 8.0 mL of THF was stirred under reflux for 3 hours. After cooling to room temperature, a 1.0 M aqueous sodium thiosulfate solution was added to the resulting mixture and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.28 g of compound 17, represented by the following formula. This compound 17: 1 H-NMR (CDCl3) δ: 8.58-8.57 (1H, m), 8.18-8.17 (1H, m), 7.87-7.82 (1H, m), 7.63-7.60 (1H, m), 7.53-7.50 (2H, m), 7.38-7.37 (2H, m), 7.28-7.24 (1H, m), 7.16-7.14 (2H, m), 4.21 (2H, s).
[0078] Preparation Example 3 2.54 g of 3-([1,1'-biphenyl]-4-ylmethyl)-5-tosyl-1,2,4-thiadiazole was added at 0°C to a mixture of 0.49 g of sodium borohydride and 50 mL of methanol, and the mixture was stirred at 0°C for 30 minutes. At room temperature, saturated aqueous ammonium chloride solution was added to the resulting mixture and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.48 g of compound 18, represented by the following formula. This compound 18: 1 H-NMR (CDCl3) δ: 9.79 (1H, s), 7.58-7.55 (4H, m), 7.42-7.40 (4H, m), 7.35-7.31 (1H, m), 4.46 (2H, s).
[0079] Intermediate Preparation Example 1 Under a nitrogen atmosphere, a mixture of 1.8 g of 1-(bromomethyl)-4-iodobenzene, 0.42 g of tetrazole, 4.0 g of potassium carbonate, and 30 mL of DMF was stirred at 70°C for 4 hours. After cooling to room temperature, water was added to the resulting mixture, and the precipitated solid was filtered off. The obtained solid was washed with water and dried under reduced pressure to obtain 1.5 g of a mixture of intermediate 1, shown in the following formula, and 1-(4-iodobenzyl)-1H-tetrazole. Intermediate 1 + 1-(4-iodobenzyl)-1H-tetrazole (a mixture of intermediate 1 and 1-(4-iodobenzyl)-1H-tetrazole, with a molar ratio of intermediate 1:1-(4-iodobenzyl)-1H-tetrazole = 2:3): 1H-NMR (CDCl3) δ: 8.51 (1.5H, s), 8.51 (1H, s), 7.77-7.74 (3H, m), 7.73-7.70 (2H, m), 7.12 (2H, d), 7.04 (3H, d), 5.73 (2H, s), 5.53 (3H, s).
[0080] Examples of compounds (including the present compound and the compound of the present invention) produced according to the above manufacturing method and examples are shown below. Formula (A-1) [In the formula, L x This represents one of formulas L0 to L42. (However, ● represents the bonding site with the benzene ring shown in formula (A-1).)
[0081]
[0082]
[0083] In the compound represented by ] (hereinafter referred to as compound (A-1)), A x However, it is a 1H-pyrazole-1-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 and R X12 A compound whose combination is one of the combinations listed in Combination A (hereinafter referred to as Compound Group SX1).
[0084] Combination A consists of substituent numbers A1 to A1617. Substituents A1 to A1617 are L in compound (A-1). x Structure and L x substituent R corresponding to the structure X8 , R X9 , R X10 , R X11 and R X12 This represents a combination of [substituent number; L], and below [substituent number; L] x ;R X8 , R X9 , R X10 , RX11 , R X12 ] is written as. For example, substituent number A2 is L x L0 is R X8 is a methyl group, R X9 , R X10 , R X11 and R X12 This refers to a combination where the atom is a hydrogen atom.
[0085] Combination A: [A1; L0; H, H, H, H, H], [A2; L0; Me, H, H, H, H], [A3; L0; Et, H, H, H, H], [A4; L0; Pr, H, H, H, H], [A5; L0; iPr, H, H, H, H], [A6; L0; tBu, H, H, H, H], [A7; L0; OMe, H, H, H, H], [A8; L0; OEt, H, H, H, H], [A9; L0; OPr, H, H, H, H], [A10; L0; OiPr, H, H, H, H], [A11; L0; CF3, H, H, H, H], [A12; L0; CF2H, H, H, H, H], [A13; L0; CFH2, H, H, H, H], [A14; L0; F, H, H, H, H], [A15; L0; Cl, H, H, H, H], [A16; L0; Br, H, H, H, H], [A17; L0; CN, H, H, H, H], [A18; L0; cPr, H, H, H, H], [A19; L0; H, Me, H, H, H], [A20; L0; H, Et, H, H, H], [A21; L0; H, Pr, H, H, H], [A22; L0; H, iPr, H, H, H], [A23; L0; H, tBu, H, H, H], [A24; L0; H, OMe, H, H, H], [A25; L0; H, OEt, H, H, H], [A26; L0; H, OPr, H, H, H], [A27; L0; H, OiPr, H, H, H], [A28; L0; H, CF3, H, H, H], [A29; L0; H, CF2H, H, H, H], [A30; L0; H, CFH2, H, H, H], [A31; L0; H, F, H, H, H], [A32; L0; H, Cl, H, H, H], [A33; L0; H, Br, H, H, H], [A34; L0; H, CN, H, H, H], [A35; L0; H, cPr, H, H, H], [A36; L0; H, H, Me, H, H], [A37; L0; H, H, Et, H, H], [A38; L0; H, H, Pr, H, H], [A39; L0; H, H, iPr, H, H], [A40; L0; H, H, tBu, H, H], [A41; L0; H, H, OMe, H, H], [A42; L0; H, H, OEt, H, H], [A43; L0; H, H, OPr, H, H], [A44; L0; H, H, OiPr, H, H], [A45; L0; H, H, CF3, H, H], [A46; L0; H, H, CF2H, H, H], [A47; L0; H, H, CFH2, H, H], [A48; L0; H, H, F, H, H], [A49; L0;H,H,Cl,H,H],[A50;L0;H,H,Br,H,H],[A51;L0;H,H,CN,H,H],[A52;L0;H,H,cPr,H,H],[A53;L0;H,H,H,Me,H],[A54;L0;H,H,H,Et,H],[A55;L0;H,H,H,Pr,H],[A56;L0;H,H,H,iPr,H],[A57;L0;H,H,H,tBu,H],[A58;L0;H,H,H,OMe,H],[A59;L0;H,H,H,OEt,H],[A60;L0;H,H,H,OPr,H],[A61;L0;H,H,H,OiPr,H],[A62;L0;H,H,H,CF3,H],[A63;L0;H,H,H,CF2H,H],[A64;L0;H,H,H,CFH2,H],[A65;L0;H,H,H,F,H],[A66;L0;H,H,H,Cl,H],[A67;L0;H,H,H,Br,H],[A68;L0;H,H,H,CN,H],[A69;L0;H,H,H,cPr,H],[A70;L0;H,H,H,H,Me],[A71;L0;H,H,H,H,Et],[A72;L0;H,H,H,H,Pr],[A73;L0;H,H,H,H,iPr],[A74;L0;H,H,H,H,tBu],[A75;L0;H,H,H,H,OMe],[A76;L0;H,H,H,H,OEt],[A77;L0;H,H,H,H,OPr],[A78;L0;H,H,H,H,OiPr],[A79;L0;H,H,H,H,CF3],[A80;L0;H,H,H,H,CF2H],[A81;L0;H,H,H,H,CFH2],[A82;L0;H,H,H,H,F],[A83;L0;H,H,H,H,Cl],[A84;L0;H,H,H,H,Br],[A85;L0;H,H,H,H,CN],[A86;L0;H,H,H,H,cPr],[A87L0;F,F,H,H,H],[A88;L0;F,H,F,H,H],[A89;L0;F,H,H,F,H],[A90;L0;F,H,H,H,F],[A91;L0;H,F,F,H,H],[A92;L0;H,F,H,F,H],[A93;L0;Cl,Cl,H,H,H],[A94;L0;Cl,H,Cl,H,H],[A95;L0;Cl,H,H,Cl,H],[A96;L0;Cl,H,H,H,Cl],[A97;L0;H,Cl,Cl,H,H],[A98;L0;H,Cl,H,Cl,H],[A99;L1;H,H,H,H,-],[A100;L1;Me,H,H,H,-],[A101;L1;Et,H,H,H,-],[A102;L1;Pr,H,H,H,-],[A103;L1;iPr,H,H,H,-],[A104;L1;tBu,H,H,H,-],[A105;L1;OMe,H,H,H,-],[A106;L1;OEt,H,H,H,-],[A107;L1;OPr,H,H,H,-],[A108;L1;OiPr,H,H,H,-],[A109;L1;CF3,H,H,H,-],[A110;L1;CF2H,H,H,H,-],[A111;L1;CFH2,H,H,H,-],[A112;L1;F,H,H,H,-],[A113;L1;Cl,H,H,H,-],[A114;L1;Br,H,H,H,-],[A115;L1;CN,H,H,H,-],[A116;L1;cPr,H,H,H,-],[A117;L1;H,Me,H,H,-],[A118;L1;H,Et,H,H,-],[A119;L1;H,Pr,H,H,-],[A120;L1;H,iPr,H,H,-],[A121;L1;H,tBu,H,H,-],[A122;L1;H,OMe,H,H,-],[A123;L1;H,OEt,H,H,-],[A124;L1;H,OPr,H,H,-],[A125;L1;H,OiPr,H,H,-],[A126;L1;H,CF3,H,H,-],[A127;L1;H,CF2H,H,H,-],[A128;L1;H,CFH2,H,H,-],[A129;L1;H,F,H,H,-],[A130;L1;H,Cl,H,H,-],[A131;L1;H,Br,H,H,-],[A132;L1;H,CN,H,H,-],[A133;L1;H,cPr,H,H,-],[A134;L1;H,H,Me,H,-],[A135;L1;H,H,Et,H,-],[A136;L1;H,H,Pr,H,-],[A137;L1;H,H,iPr,H,-],[A138;L1;H,H,tBu,H,-],[A139;L1;H,H,OMe,H,-],[A140;L1;H,H,OEt,H,-],[A141;L1;H,H,OPr,H,-],[A142;L1;H,H,OiPr,H,-],[A143;L1;H,H,CF3,H,-],[A144;L1;H,H,CF2H,H,-],[A145;L1;H,H,CFH2,H,-],[A146;L1;H,H,F,H,-],[A147;L1;H,H,Cl,H,-],[A148;L1;H,H,Br,H,-],[A149;L1;H,H,CN,H,-],[A150;L1;H,H,cPr,H,-],[A151;L1;H,H,H,Me,-],[A152;L1;H,H,H,Et,-],[A153;L1;H,H,H,Pr,-],[A154;L1;H,H,H,iPr,-],[A155;L1;H,H,H,tBu,-],[A156;L1;H,H,H,OMe,-],[A157;L1;H,H,H,OEt,-],[A158;L1;H,H,H,OPr,-],[A159;L1;H,H,H,OiPr,-],[A160;L1;H,H,H,CF3,-],[A161;L1;H,H,H,CF2H,-],[A162;L1;H,H,H,CFH2,-],[A163;L1;H,H,H,F,-],[A164;L1;H,H,H,Cl,-],[A165;L1;H,H,H,Br,-],[A166;L1;H,H,H,CN,-],[A167;L1;H,H,H,cPr,-],[A168;L1;F,F,H,H,-],[A169;L1;F,H,F,H,-],[A170;L1;F,H,H,F,-],[A171;L1;H,F,F,H,-],[A172;L1;H,F,H,F,-],[A173;L1;H,H,F,F,-],[A174;L1;Cl,Cl,H,H,-],[A175;L1;Cl,H,Cl,H,-],[A176;L1;Cl,H,H,Cl,-],[A177;L1;H,Cl,Cl,H,-],[A178;L1;H,Cl,H,Cl,-],[A179;L1;H,H,Cl,Cl,-],[A180;L2;H,H,H,H,-],[A181;L2;Me,H,H,H,-],[A182;L2;Et,H,H,H,-],[A183;L2;Pr,H,H,H,-],[A184;L2;iPr,H,H,H,-],[A185;L2;tBu,H,H,H,-],[A186;L2;OMe,H,H,H,-],[A187;L2;OEt,H,H,H,-],[A188;L2;OPr,H,H,H,-],[A189;L2;OiPr,H,H,H,-],[A190;L2;CF3,H,H,H,-],[A191;L2;CF2H,H,H,H,-],[A192;L2;CFH2,H,H,H,-],[A193;L2;F,H,H,H,-],[A194;L2;Cl,H,H,H,-],[A195;L2;Br,H,H,H,-],[A196;L2;CN,H,H,H,-],[A197;L2;cPr,H,H,H,-],[A198;L2;H,Me,H,H,-],[A199;L2;H,Et,H,H,-],[A200;L2;H,Pr,H,H,-],[A201;L2;H,iPr,H,H,-],[A202;L2;H,tBu,H,H,-],[A203;L2;H,OMe,H,H,-],[A204;L2;H,OEt,H,H,-],[A205;L2;H,OPr,H,H,-],[A206;L2;H,OiPr,H,H,-],[A207;L2;H,CF3,H,H,-],[A208;L2;H,CF2H,H,H,-],[A209;L2;H,CFH2,H,H,-],[A210;L2;H,F,H,H,-],[A211;L2;H,Cl,H,H,-],[A212;L2;H,Br,H,H,-],[A213;L2;H,CN,H,H,-],[A214;L2;H,cPr,H,H,-],[A215;L2;H,H,Me,H,-],[A216;L2;H,H,Et,H,-],[A217;L2;H,H,Pr,H,-],[A218;L2;H,H,iPr,H,-],[A219;L2;H,H,tBu,H,-],[A220;L2;H,H,OMe,H,-],[A221;L2;H,H,OEt,H,-],[A222;L2;H,H,OPr,H,-],[A223;L2;H,H,OiPr,H,-],[A224;L2;H,H,CF3,H,-],[A225;L2;H,H,CF2H,H,-],[A226;L2;H,H,CFH2,H,-],[A227;L2;H,H,F,H,-],[A228;L2;H,H,Cl,H,-],[A229;L2;H,H,Br,H,-],[A230;L2;H,H,CN,H,-],[A231;L2;H,H,cPr,H,-],[A232;L2;H,H,H,Me,-],[A233;L2;H,H,H,Et,-],[A234;L2;H,H,H,Pr,-],[A235;L2;H,H,H,iPr,-],[A236;L2;H,H,H,tBu,-],[A237;L2;H,H,H,OMe,-],[A238;L2;H,H,H,OEt,-],[A239;L2;H,H,H,OPr,-],[A240;L2;H,H,H,OiPr,-],[A241;L2;H,H,H,CF3,-] . CN,-],[A248;L2;H,H,H,cPr,-],[A249;L2;F,F,H,H,-],[A250;L2;F,H, F,H,-],[A251;L2;F,H,H,F,-],[A252;L2;H,F,F,H,-],[A253;L2;H,F,H, F,-],[A254;L2;H,H,F,F,-],[A255;L2;Cl,Cl,H,H,-],[A256;L2;Cl,H,Cl,H,-],[A257;L2;Cl,H,H,Cl,-],[A258;L2;H,Cl,Cl,H,-],[A259;L2;H, Cl,H,Cl,-],[A260;L2;H,H,Cl,Cl,-],[A261;L2;H,H,H,H,-],[A262;L2;Me,H,H,H,-],[A263;L2;Et,H,H,H,-],[A264;L2;Pr,H,H,H,-],[A265;L 2;iPr,H,H,H,-],[A266;L2;tBu,H,H,H,-],[A267;L2;OMe,H,H,H,-],[A268;L2;OEt,H,H,H,-],[A269;L3;OPr,H,H,H,-],[A270;L3;OiPr,H,H,H,- [A271;L3;CF3,H,H,H,-],[A272;L3;CF2H,H,H,H,-],[A273;L3;CFH2,H,H,H,-],[A274;L3;F,H,H,H,-],[A275;L3;Cl,H,H,H,-],[A276;L3;Br,H,H,H,-],[A277;L3;CN,H,H,H,-],[A278;L3;cPr,H,H,H,-],[A279;L3;H,Me,H,H,-],[A280;L3;H,Et,H,H,-],[A281;L3;H,Pr,H,H,-],[A282;L3;H,iPr,H,H,-],[A283;L3;H,tBu,H,H,-],[A284;L3;H,OMe,H,H,-],[A285;L3;H,OEt,H,H,-],[A286;L3;H,OPr,H,H,-],[A287;L3;H,OiPr,H,H,-],[ A288;L3;H,CF3,H,H,-],[A289;L3;H,CF2H,H,H,-],[A290;L3;H,CFH2,H,H,-],[A291;L3;H,F,H,H,-],[A292;L3;H,Cl,H,H,-],[A293;L3;H,Br,H,H [A294;L3;H,CN,H,H,-],[A295;L3;H,cPr,H,H,-],[A296;L3;H,H,Me,H,-],[A297;L3;H,H,Et,H,-],[A298;L3;H,H,Pr,H,-],[A299;L3;H,H,iPr,H,-],[A300;L3;H,H,tBu,H,-],[A301;L3;H,H,OMe,H,-],[A302;L3;H,H,OEt,H,-],[A303;L3;H,H,OPr,H,-],[A304;L3;H,H,OiPr,H,-],[A305;L 3;H,H,CF3,H,-],[A306;L3;H,H,CF2H,H,-],[A307;L3;H,H,CFH2,H,-],[A308;L3;H,H,F,H,-],[A309;L3;H,H,Cl,H,-],[A310;L3;H,H,Br,H,-],[A311;L3;H,H,CN,H,-],[A312;L3;H,H,cPr,H,-],[A313;L3;H,H,H,Me,-],[A314;L3;H,H,H,Et,-],[A315;L3;H,H,H,Pr,-],[A316;L3;H,H,H,iPr,-] [A317;L3;H,H,H,tBu,-], [A318;L3;H,H,H,OMe,-], [A319;L3;H,H,H,OEt,-], [A320;L3;H,H,H,OPr,-], [A321;L3;H,H,H,OiPr,-], [A322;L3;H,H,H,CF3,-], [A323;L3;H,H,H,CF2H,-], [A324;L3;H,H,H,CFH2,-], [A325;L3;H,H,H,F,-], [A326;L3;H,H,H,Cl,-], [A327;L3;H,H,H,Br,-], [A328;L3;H,H,H,CN,-],[A329;L3;H,H,H,cPr,-],[A330;L3;F,F,H,H,-],[A331;L3;F,H,F,H,-],[A332;L3;F,H,H,F,-],[A333;L3;H,F,F,H,-],[A334;L3;H,F,H,F,-],[A335;L3;H,H,F,F,-],[A336;L3;Cl,Cl,H,H,-],[A337;L3;Cl,H,Cl,H,-],[A338;L3;Cl,H,H,Cl,-],[A339;L3;H,Cl,Cl,H,-],[A340;L 3;H,Cl,H,Cl,-],[A341;L3;H,H,Cl,Cl,-],[A342;L4;H,H,H,-,-],[A343L4Me,H,H,-,-],[A344L4Et,H,H,-,-],[A345L4Pr,H,H,-,-],[A346L4iPr, H,H,-,-],[A347L4tBu,H,H,-,-],[A348L4OMe,H,H,-,-],[A349L4OEt,H,H,-,-],[A350L4OPr,H,H,-,-],[A351L4OiPr,H,H,-,-],[A352L4CF3,H,H, -,-],[A353L4CF2H,H,H,-,-],[A354L4CFH2,H,H,-,-],[A355L4F,H,H,-,-],[A356;L4;Cl,H,H,-,-],[A357;L4;Br,H,H,-,-],[A358;L4;CN,H,H,-, -],[A359;L4;cPr,H,H,-,-],[A360;L4;H,Me,H,-,-],[A361;L4;H,Et,H, -,-],[A362;L4;H,Pr,H,-,-],[A363;L4;H,iPr,H,-,-],[A364;L4;H,OMe, H,-,-]. r,H,-,-],[A371;L4;H,H,Me,-,-],[A372;L4;H,H,Et,-,-],[A373;L4;H, H,Pr,-,-],[A374;L4;H,H,iPr,-,-],[A375;L4;H,H,OMe,-,-],[A376;L4;H,H,CF3,-,-],[A377;L4;H,H,F,-,-],[A378;L4;H,H,Cl,-,-],[A379;L4;H,H,Br,-,-],[A380;L4;H,H,CN,-,-],[A381;L4;H,H,cPr,-,-],[A382;L4;F,F,H,-,-],[A383;L4;F,H,F,-,-],[A384;L4;Cl,Cl,H,-,-],[A385;L4;Cl,H,Cl,-,-],[A386;L4;F,F,F,-,-],[A387;L4;Cl,Cl,Cl,-,-],[A388;L5;H,H,H,-,-],[A389L5Me,H,H,-,-],[A390L5Et,H,H,-,-],[A391L5Pr,H,H,-,-],[A392L5iPr,H,H,-,-],[A393L5tBu,H,H,-,-],[A394L5OMe,H,H,-,-],[A395L5OEt,H,H,-,-],[A396L5OPr,H,H,-,-],[A397L5OiPr,H,H,-,-],[A398L5CF3,H,H,-,-],[A399L5CF2H,H,H,-,-],[A400L5CFH2,H,H,-,-],[A401L5F,H,H,-,-],[A402;L5;Cl,H,H,-,-],[A403;L5;Br,H,H,-,-],[A404;L5;CN,H,H,-,-],[A405;L5;cPr,H,H,-,-],[A406;L5;H,Me,H,-,-],[A407;L5;H,Et,H,-,-],[A408;L5;H,Pr,H,-,-],[A409;L5;H,iPr,H,-,-],[A410;L5;H,OMe,H,-,-],[A411;L5;H,CF3,H,-,-],[A412;L5;H,F,H,-,-],[A413;L5;H,Cl,H,-,-],[A414;L5;H,Br,H,-,-],[A415;L5;H,CN,H,-,-],[A416;L5;H,cPr,H,-,-],[A417;L5;H,H,Me,-,-],[A418;L5;H,H,Et,-,-],[A419;L5;H,H,Pr,-,-],[A420;L5;H,H,iPr,-,-],[A421;L5;H,H,OMe,-,-],[A422;L5;H,H,CF3,-,-],[A423;L5;H,H,F,-,-],[A424;L5;H,H,Cl,-,-],[A425;L5;H,H,Br,-,-],[A426;L5;H,H,CN,-,-],[A427;L5;H,H,cPr,-,-],[A428;L5;F,F,H,-,-],[A429;L5;F,H,F,-,-],[A430;L5;Cl,Cl,H,-,-],[A431;L5;Cl,H,Cl,-,-],[A432;L5;F,F,F,-,-],[A433;L5;Cl,Cl,Cl,-,-],[A434;L6;H,H,H,-,-],[A435;L6;Me,H,H,-,-],[A436;L6;Et,H,H,-,-],[A437;L6;Pr,H,H,-,-],[A438;L6;iPr,H,H,-,-],[A439;L6;OMe,H,H,-,-],[A440;L6;CF3,H,H,-,-],[A441;L6;F,H,H,-,-],[A442;L6;Cl,H,H,-,-],[A443;L6;Br,H,H,-,-],[A444;L6;CN,H,H,-,-],[A445;L6;cPr,H,H,-,-],[A446;L6;H,Me,H,-,-],[A447;L6;H,Et,H,-,-],[A448;L6;H,Pr,H,-,-],[A449;L6;H,iPr,H,-,-],[A450;L6;H,OMe,H,-,-],[A451;L6;H,CF3 ,H,-,-],[A452;L6;H,F,H,-,-],[A453;L6;H,Cl,H,-,-],[A454;L6;H,Br,H,-,-],[A455;L6;H,CN,H,-,-],[A456;L6;H,cPr,H,-,-],[A457;L6;H,H,Me,-,-],[A458;L6;H,H,Et,-,-],[A459;L6;H,H,Pr,-,-],[A460;L6;H,H,iPr,-,-],[A461;L6;H,H,OMe,-,-],[A462;L6;H,H,CF3,-,-],[A463;L6;H,H,F,-,-],[A464;L6;H,H,Cl,-,-],[A465;L6;H,H,Br,-,-],[A466;L6;H,H,CN,-,-],[A467;L6;H,H,cPr,-,-],[A468;L6;F,F,H,-,-],[A469;L6;F,H,F,-,-],[A470;L6;H,F,F,-,-],[A471;L6;Cl, Cl, H, -, -], [A472; L6; Cl, H, Cl, -, -], [A473; L6; H, Cl, Cl, -, -], [A474; L6; F, F, F, -, -], [A475; L6; Cl, Cl, Cl, -, -], [A476; L7; H, H, H, -, -], [A477; L7; Me, H, H, -, -], [A478; L7; Et, H, H, -, -], [A479; L7; Pr, H, H, -, -], [A480; L7; iPr, H, H, -, -], [A481; L7; Ome, H, H, -, -], [A482; L7; CF3, H, H, -, -], [ A483;L7;F,H,H,-,-],[A484;L7;Cl,H,H,-,-],[A485;L7;Br,H,H,-,-],[A486;L7;CN,H,H,-,-],[A487;L7;cPr,H,H,-,-],[A488;L7;H,Me,H,-,-], [A489;L7;H,Et,H,-,-],[A490;L7;H,Pr,H,-,-],[A491;L7;H,iPr,H,-,- ],[A492;L7;H,OMe,H,-,-],[A493;L7;H,CF3,H,-,-],[A494;L7;H,F,H,-, -],[A495;L7;H,Cl,H,-,-],[A496;L7;H,Br,H,-,-],[A497;L7;H,CN,H,-,-],[A498;L7;H,cPr,H,-,-],[A499;L7;H,H,Me,-,-],[A500;L7;H,H,Et, -,-],[A501;L7;H,H,Pr,-,-],[A502;L7;H,H,iPr,-,-],[A503;L7;H,H,O Me,-,-],[A504;L7;H,H,CF3,-,-],[A505;L7;H,H,F,-,-],[A506;L7;H,H, Cl,-,-, 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,-,-,-,-],[A1376;L35;Cl,-,-,-,-],[A1377;L35;Br,-,-,-,-],[A1378;L35;CN,-,-,-,-],[A1379;L35;cPr,-,-,-,-],[A1380;L36;H,H,-,-,-],[A1381;L36;Me,H,-,-,-],[A1382;L36;Et,H,-,-,-],[A1383;L36;Pr,H,-,-,-],[A1384;L36,Bu,H,-,-,-],[A1385;L36,iPr,H,-,-,-],[A1386;L36,CF2H,H,-,-,-],[A1387;L36,CF3,H,-,-,-],[A1388;L36,cPr,H,-,-,-],[A1389;L36,F,H,-,-,-],[A1390;L36,Cl,H,-,-,-],[A1391;L36,Br,H,-,-,-],[A1392;L36,Me,Me,-,-,-],[A1393;L37,H,H,-,-,-],[A1394;L37,Me,H,-,-,-],[A1395;L37,Et,H,-,-,-],[A1396;L37,Pr,H,-,-,-],[A1397;L37,iPr,H,-,-,-],[A1398;L37,OMe,H,-,-,-],[A1399;L37,F,H,-,-,-],[A1400;L37,Cl,H,-,-,-],[A1401;L37,Br,H,-,-,-],[A1402;L37,CN,H,-,-,-],[A1403;L37,cPr,H,-,-,-],[A1404;L38,H,-,-,-,-],[A1405;L38,Me,-,-,-,-],[A1406;L38,Et,-,-,-,-],[A1407;L38,Pr,-,-,-,-],[A1408;L38;iPr,-,-,-,-],[A1409;L38;OMe,-,-,-,-],[A1410;L38;F,-,-,-,-],[A1411;L38;Cl,-,-,-,-],[A1412;L38;Br,-,-,-,-],[A1413;L38;CN,-,-,-,-],[A1414;L38;cPr,-,-,-,-],[A1415;L39;H,H,H,-,-],[A1416;L39;Me,H,H,-,-],[A1417;L39;Et,H,H,-,-],[A1418;L39;Pr,H,H,-,-],[A1419;L39;iPr,H,H,-,-],[A1420;L39;OMe,H,H,-,-],[A1421;L39;Cl,H,H,-,-],[A1422;L39;Br,H,H,-,-],[A1423;L39;CN,H,H,-,-],[A1424;L39;cPr,H,H,-,-],[A1425;L39;H,H,Me,-,-],[A1426;L39;H,H,Et,-,-],[A1427;L39;H,H,Pr,-,-],[A1428;L39;H,H,iPr,-,-],[A1429;L39;H,H,OMe,-,-],[A1430;L39;H,H,Cl,-,-],[A1431;L39;H,H,Br,-,-],[A1432;L39;H,H,CN,-,-],[A1433;L39;H,H,cPr,-,-],[A1434;L39;Me,Me,H,-,-],[A1435;L39;Cl,Cl,H,-,-],[A1436;L39;Me,H,Me,-,-],[A1437;L39;Me,Me,Me,-,-],[A1438;L40;Et,-,-,-,-],[A1439;L40;Pr,-,-,-,-],[A1440;L40;iPr,-,-,-,-],[A1441;L40;Bu,-,-,-,-],[A1442;L40;iBu,-,-,-,-],[A1443;L40;sBu,-,-,-,-],[A1444;L40;tBu,-,-,-,-],[A1445;L40;Pen,-,-,-,-],[A1446;L40;Hex,-,-,-,-],[A1447;L40;cPr,-,-,-,-],[A1448;L40;cBu,-,-,-,-],[A1449;L40;cPen,-,-,-,-],[A1450;L40;cHex,-,-,-,-],[A1451;L40;CH2CH=CH2,-,-,-,-],[A1452;L40;CH2CH=CHCH3,-,-,-,-],[A1453;L40;CH2CH=C(CH3)2,-,-,-,-],[A1454;L40;CH2CH=CF2,-,-,-,-],[A1455;L40;CH2CH=CCl2,-,-,-,-],[A1456;L40;CH2CH=CHCH2CH3,-,-,-,-],[A1457;L40;CH2CH=CH(CH2)2CH3,-,-,-,-],[A1458;L40;CH2C(CH3)=CH2,-,-,-,-],[A1459;L40;CH2C(CH3)=CHCH3,-,-,-,-],[A1460;L40;CH2C(CH3)=C(CH3)2,-,-,-,-],[A1461;L40;CH2C(CH3)=CHCH2CH3,-,-,-,-],[A1462;L40;CH2C(CH3)=CH(CH2)2CH3,-,-,-,-],[A1463;L40;CH2CF=CH2,-,-,-,-],[A1464;L40;CH2CF=CHCH3,-,-,-,-],[A1465;L40;CH2CF=C(CH3)2,-,-,-,-],[A1466;L40;CH2CF=CF2,-,-,-,-],[A1467;L40;CH2CF=CHCH2CH3,-,-,-,-],[A1468;L40;CH2CF=CH(CH2)2CH3,-,-,-,-],[A1469;L40;CH2CCl=CH2,-,-,-,-],[A1470;L40;CH2CCl=CHCH3,-,-,-,-],[A1471;L40;CH2CCl=C(CH3)2,-,-,-,-],[A1472;L40;CH2CCl=CCl2,-,-,-,-],[A1473;L40;CH2CCl=CHCH2CH3,-,-,-,-],[A1474;L40;CH2CCl=CH(CH2)2CH3,-,-,-,-],[A1475;L40;(CH2)2CH=CH2,-,-,-,-],[A1476;L40;(CH2)2CH=CHCH3,-,-,-,-],[A1477;L40;(CH2)2CH=CHCH2CH3,-,-,-,-],[A1478;L40;(CH2)2CH=C(CH3)2,-,-,-,-],[A1479;L40;(CH2)2C(CH3)=CH2,-,-,-,-],[A1480;L40;(CH2)2C(CH3)=CHCH3,-,-,-,-],[A1481;L40;(CH2)2C(CH3)=CHCH2CH3,-,-,-,-],[A1482;L40;(CH2)2C(CH3)=C(CH3)2,-,-,-,-],[A1483;L40;(CH2)3cPr,-,-,-,-],[A1484;L40;(CH2)5CH3,-,-,-,-],[A1485;L40;(CH2)3CH(CH3)2,-,-,-,-],[A1486;L40;(CH2)2CH(CH3)CH2CH3,-,-,-,-],[A1487;L40;CH2CH(CH3)(CH2)2CH3,-,-,-,-],[A1488;L40;CH(CH3)(CH2)3CH3,-,-,-,-],[A1489;L40;CH2CH(CH2CH3)2,-,-,-,-],[A1490;L40;CH2C≡CH,-,-,-,-],[A1491;L40;CH2C≡CCH3,-,-,-,-],[A1492;L40;CH2C≡CCH2CH3,-,-,-,-],[A1493;L40;CH2C≡CcPr,-,-,-,-],[A1494;L40;(CH2)2C≡CH,-,-,-,-],[A1495;L40;(CH2)2C≡CCH3,-,-,-,-],[A1496;L40;(CH2)2C≡CCH2CH3,-,-,-,-],[A1497;L40;(CH2)2C≡CcPr,-,-,-,-],[A1498;L41;Et,-,-,-,-],[A1499;L41;Pr,-,-,-,-],[A1500;L41;iPr,-,-,-,-],[A1501;L41;cPr,-,-,-,-],[A1502;L41;Bu,-,-,-,-],[A1503;L41;iBu,-,-,-,-],[A1504;L41;sBu,-,-,-,-],[A1505;L41;tBu,-,-,-,-],[A1506;L41;cBu,-,-,-,-],[A1507;L41;Pen,-,-,-,-],[A1508;L41;cPen,-,-,-,-],[A1509;L41;Hex,-,-,-,-],[A1510;L41;cHex,-,-,-,-],[A1511;L41;CH2CH=CH2,-,-,-,-],[A1512;L41;CH2CH=CHCH3,-,-,-,-],[A1513;L41;CH2CH=C(CH3)2,-,-,-,-],[A1514;L41;CH2CH=CF2,-,-,-,-],[A1515;L41;CH2CH=CCl2,-,-,-,-],[A1516;L41;CH2CH=CHCH2CH3,-,-,-,-],[A1517;L41;CH2CH=CH(CH2)2CH3,-,-,-,-],[A1518;L41;CH2C(CH3)=CH2,-,-,-,-],[A1519;L41;CH2C(CH3)=CHCH3,-,-,-,-],[A1520;L41;CH2C(CH3)=C(CH3)2,-,-,-,-],[A1521;L41;CH2C(CH3)=CHCH2CH3,-,-,-,-],[A1522;L41;CH2C(CH3)=CH(CH2)2CH3,-,-,-,-],[A1523;L41;CH2CF=CH2,-,-,-,-],[A1524;L41;CH2CF=CHCH3,-,-,-,-],[A1525;L41;CH2CF=C(CH3)2,-,-,-,-],[A1526;L41;CH2CF=CF2,-,-,-,-],[A1527;L41;CH2CF=CHCH2CH3,-,-,-,-],[A1528;L41;CH2CF=CH(CH2)2CH3,-,-,-,-],[A1529;L41;CH2CCl=CH2,-,-,-,-],[A1530;L41;CH2CCl=CHCH3,-,-,-,-],[A1531;L41;CH2CCl=C(CH3)2,-,-,-,-],[A1532;L41;CH2CCl=CCl2,-,-,-,-],[A1533;L41;CH2CCl=CHCH2CH3,-,-,-,-],[A1534;L41;CH2CCl=CH(CH2)2CH3,-,-,-,-],[A1535;L41;(CH2)2CH=CH2,-,-,-,-],[A1536;L41;(CH2)2CH=CHCH3,-,-,-,-],[A1537;L41;(CH2)2CH=CHCH2CH3,-,-,-,-],[A1538;L41;(CH2)2CH=C(CH3)2,-,-,-,-],[A1539;L41;(CH2)2C(CH3)=CH2,-,-,-,-],[A1540;L41;(CH2)2C(CH3)=CHCH3,-,-,-,-],[A1541;L41;(CH2)2C(CH3)=CHCH2CH3,-,-,-,-],[A1542;L41;(CH2)2C(CH3)=C(CH3)2,-,-,-,-],[A1543;L41;(CH2)3cPr,-,-,-,-],[A1544;L41;(CH2)5CH3,-,-,-,-],[A1545;L41;(CH2)3CH(CH3)2,-,-,-,-],[A1546;L41;(CH2)2CH(CH3)CH2CH3,-,-,-,-],[A1547;L41;CH2CH(CH3)(CH2)2CH3,-,-,-,-],[A1548;L41;CH(CH3)(CH2)3CH3,-,-,-,-],[A1549;L41;CH2CH(CH2CH3)2,-,-,-,-],[A1550;L41;CH2C≡CH,-,-,-,-],[A1551;L41;CH2C≡CCH3,-,-,-,-],[A1552;L41;CH2C≡CCH2CH3,-,-,-,-],[A1553;L41;CH2C≡CcPr,-,-,-,-],[A1554;L41;(CH2)2C≡CH,-,-,-,-],[A1555;L41;(CH2)2C≡CCH3,-,-,-,-],[A1556;L41;(CH2)2C≡CCH2CH3,-,-,-,-],[A1557;L41;(CH2)2C≡CcPr,-,-,-,-],[A1558;L42;Et,-,-,-,-],[A1559;L42;Pr,-,-,-,-],[A1560;L42;iPr,-,-,-,-],[A1561;L42;cPr,-,-,-,-],[A1562;L42;Bu,-,-,-, -],[A1563;L42;iBu,-,-,-,-],[A1564;L42;sBu,-,-,-,-],[A1565;L42;tBu,-,-,-,-],[A1566;L42;cBu,-,-,-,-],[A1567;L42;Pen,-,-,-,-],[A1568;L42;cPen,-,-,-,-],[A1569;L42;Hex,-,-,-,-],[A1570;L42;cHex,-,-,-,-],[A1571;L42;CH2CH=CH2,-,-,-,-],[A1572;L42;CH2CH=CHCH3,-,-,-,-],[A1573;L42;CH2CH=C(CH3)2,-,-,-,-],[A1574;L42;CH2CH=CF2,-,-,-,-],[A1575;L42;CH2CH=CCl2,-,-,-,-],[A1576;L42;CH2CH=CHCH2CH3,-,-,-,-],[A1577;L42;CH2CH=CH(CH2)2CH3,-,-,-,-],[A1578;L42;CH2C(CH3)=CH2,-,-,-,-],[A1579;L42;CH2C(CH3)=CHCH3,-,-,-,-],[A1580;L42;CH2C(CH3)=C(CH3)2,-,-,-,-],[A1581;L42;CH2C(CH3)=CHCH2CH3,-,-,-,-],[A1582;L42;CH2C(CH3)=CH(CH2)2CH3,-,-,-,-],[A1583;L42;CH2CF=CH2,-,-,-,-],[A1584;L42;CH2CF=CHCH3,-,-,-,-],[A1585;L42;CH2CF=C(CH3)2,-,-,-,-],[A1586;L42;CH2CF=CF2,-,-,-,-],[A1587;L42;CH2CF=CHCH2CH3,-,-,-,-],[A1588;L42;CH2CF=CH(CH2)2CH3,-,-,-,-],[A1589;L42;CH2CCl=CH2,-,-,-,-],[A1590;L42;CH2CCl=CHCH3,-,-,-,-],[A1591;L42;CH2CCl=C(CH3)2,-,-,-,-],[A1592;L42;CH2CCl=CCl2,-,-,-,-],[A1593;L42;CH2CCl=CHCH2CH3,-,-,-,-],[A1594;L42;CH2CCl=CH(CH2)2CH3,-,-,-,-],[A1595;L42;(CH2)2CH=CH2,-,-,-,-],[A1596;L42;(CH2)2CH=CHCH3,-,-,-,-],[A1597;L42;(CH2)2CH=CHCH2CH3,-,-,-,-],[A1598;L42;(CH2)2CH=C(CH3)2,-,-,-,-],[A1599;L42;(CH2)2C(CH3)=CH2,-,-,-,-],[A1600;L42;(CH2)2C(CH3)=CHCH3,-,-,-,-],[A1601;L42;(CH2)2C(CH3)=CHCH2CH3,-,-,-,-],[A1602;L42;(CH2)2C(CH3)=C(CH3)2,-,-,-,-],[A1603;L42;(CH2)3cPr,-,-,-,-],[A1604;L42;(CH2)5CH3,-,-,-,-],[A1605;L42;(CH2)3CH(CH3)2,-,-,-,-],[A1606;L42;(CH2)2CH(CH3)CH2CH3,-,-,-,-],[A1607;L42;CH2CH(CH3)(CH2)2CH3,-,-,-,-],[A1608;L42;CH(CH3)(CH2)3CH3,-,-,-,-],[A1609;L42;CH2CH(CH2CH3)2,-,-,-,-],[A1610;L42;CH2C≡CH,-,-,-,-],[A1611;L42;CH2C≡CCH3,-,-,-,-],[A1612;L42;CH2C≡CCH2CH3,-,-,-,-],[A1613;L42;CH2C≡CcPr,-,-,-,-],[A1614;L42;(CH2)2C≡CH,-,-,-,-],[A1615;L42;(CH2)2C≡CCH3,-,-,-,-],[A1616;L 42;(CH2)2C≡CCH2CH3,-,-,-,-],[A1617;L42;(CH2)2C≡CcPr,-,-,-,-].;
[0086] In compound (A-1), A x However, it is a 1,2,3-triazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX2). In compound (A-1), A x However, it is a 4-methyl-1,2,3-triazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX3). In compound (A-1), A x However, it is a 4,5-dimethyl-1,2,3-triazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX4). In compound (A-1), A x However, it is a tetrazole-2-yl group, R 1x, and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX5). In compound (A-1), A x However, it is a 5-methyl-tetrazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX6). In compound (A-1), A x However, it is an isothiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX7). In compound (A-1), A x However, it is an isoxazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX8). In compound (A-1), A xHowever, it is a 5-methyl-isothiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX9). In compound (A-1), A x However, it is a 5-methyl-isoxazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX10). In compound (A-1), A x However, it is an oxazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX11). In compound (A-1), A x However, it is a thiazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX12). In compound (A-1), A x However, it is a 4-methyl-oxazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX13). In compound (A-1), A x However, it is a 4-methyl-thiazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX14). In compound (A-1), A x However, it is a 5-methyl-oxazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX15). In compound (A-1), A x However, it is a 5-methyl-thiazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , RX10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX16). In compound (A-1), A x However, it is a 1,2,4-oxadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX17). In compound (A-1), A x However, it is a 1,2,4-thiadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX18). In compound (A-1), A x However, it is a 5-methyl-1,2,4-oxadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX19). In compound (A-1), A x However, it is a 5-methyl-1,2,4-thiadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that representx substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX20). In compound (A-1), A x However, it is a 5-ethyl-1,2,4-oxadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX21). In compound (A-1), A x However, it is a 5-ethyl-1,2,4-thiadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX22). In compound (A-1), A x However, it is a 5-cyclopropyl-1,2,4-oxadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX23). In compound (A-1), A xHowever, it is a 5-cyclopropyl-1,2,4-thiazadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX24). In compound (A-1), A x However, it is a pyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX25). In compound (A-1), A x However, it is a pyridazine-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX26). In compound (A-1), A x However, it is a pyrimidine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX27). In compound (A-1), A x However, it is a pyrimidine-4-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX28). In compound (A-1), A x However, it is a pyrazine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX29). In compound (A-1), A x However, it is a 3-methylpyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX30). In compound (A-1), A x However, it is a 3-chloropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , RX11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX31). In compound (A-1), A x However, it is a 3-fluoropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX32). In compound (A-1), A x However, it is a 4-methylpyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX33). In compound (A-1), A x However, it is a 4-chloropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX34). In compound (A-1), A x However, it is a 4-fluoropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8, R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX35). In compound (A-1), A x However, it is a 5-methylpyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX36). In compound (A-1), A x However, it is a 5-chloropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in combination A (hereinafter referred to as compound group SX37). In compound (A-1), A x However, it is a 5-fluoropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by X8 , R X9 , R X10 , R X11 , and R X12 A compound whose combination is one of the combinations listed in Combination A (hereinafter referred to as Compound Group SX38).
[0087] Formula (A-2) [In the formula, L x This represents one of formulas L43 to L50. (However, ● represents the bonding site with the benzene ring shown in formula (A-2).) In the compound represented by ] (hereinafter referred to as compound (A-2)), A x However, it is a 1H-pyrazole-1-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in Combination B (hereinafter referred to as Compound Group SX39).
[0088] Combination B consists of substituent numbers B1 to B143. Substituents B1 to B143 are L in compound (A-2). x Structure and L x substituent R corresponding to the structure Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 This represents a combination of [substituent number; L], and below [substituent number; L] x ;R Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , R Y10 ] is written as. For example, substituent number B2 is L x L43 and R Y1 is a methyl group, R Y2 , R Y3 , R Y4 , R Y5 , and R Y6 This refers to a combination where the atom is a hydrogen atom.
[0089] Combination B: [B1; L43; H, H, H, H, H, H, -, -, -, -], [B2; L43; Me, H, H, H, H, H, -, -, -, -], [B3; L43; F, H, H, H, H, H, -, -, -, -], [B4; L43; Cl, H, H, H, H, H, -, -, -, -], [B5; L43; F, F, H, H, H, H, -, -, -, -], [B6; L43; Cl, Cl, H, H, H, H, -, -, -, -], [B7; L43; Me, Me, H, H, H, H, -, -, -, -], [B8; L43; H, H, F, H, H, H, -, -, -, -], [B9; L43; H, H, Cl, H, H, H, -, -, -, -], [B10; L43; H, H, Me, H, H, H, -, -, -, -], [B11; L43; H, H, F, F, H, H, -, -, -, -], [B12; L43; H, H, Cl, Cl, H, H, -, -, -, -], [B13; L43; H, H, Me, Me, H, H, -, -, -, -], [B14; L43; H, H, H, H, F, H, -, -, -, -], [B15; L43; H, H, H, H, Cl, H, -, -, -, -], [B16; L43; H, H, H, H, Me, H, -, -, -, -], [B17; L43; H, H, H, H, F, F, -, -, -, -], [B18; L43; H, H, H, H, Cl, Cl, -, -, -, -], [B19; L43; H, H, H, H, Me, Me, -, -, -, -], [B20; L43; Me, H, Me, H, H, H, -, -, -, -], [B21; L43; Me, Et, H, H, H, H, -, -, -, -], [B22; L43; H, H, H, H, Me, Et, -, -, -, -], [B23; L43; H, H, H, H, Et, H, -, -, -, -], [B24; L43; H, H, H, H, cPr, H, -, -, -, -], [B25; L43; H, H, Et, H, H, H, -, -, -, -], [B26; L43; H, H, cPr, H, H, H, -, -, -, -], [B27; L43; Et, H, H, H, H, H, -, -, -, -], [B28; L43; cPr, H, H, H, H, H, -, -, -, -], [B29; L44; H, H, H, H, H, H, H, H, -, -], [B30; L44; Me, H, H, H, H, H, H, H, -, -], [B31; L44; F, H, H, H, H, H, H, H, -, -], [B32; L44; Cl, H, H, H, H, H, H, H, -, -], [B33; L44;H,F,F,H,H,H,H,H,-,-],[B34;L44;H,Cl,Cl,H,H,H,H,H,-,-],[B35;L44;H,Me,Me,H,H,H,H,H,-,-],[B36;L44;H,H,H,F,F,H,H,H,-,-],[B37;L44;H,H,H,Cl,Cl,H,H,H,-,-],[B38;L44;H,H,H,Me,Me,H,H,H,-,-],[B39;L44;H,H,H,H,H,F,F,H,-,-],[B40;L44;H,H,H,H,H,Cl,Cl,H,-,-],[B41;L44;H,H,H,H,H,Me,Me,H,-,-],[B42;L44;F,H,H,H,H,H,H,F,-,-],[B43;L44;Cl,H,H,H,H,H,H,Cl,-,-],[B44;L44;Me,H,H,H,H,H,H,Me,-,-],[B45;L45;H,H,H,H,H,H,H,-,-,-],[B46;L45;Me,H,H,H,H,H,H,-,-,-],[B47;L45;F,H,H,H,H,H,H,-,-,-],[B48;L45;Cl,H,H,H,H,H,H,-,-,-],[B49;L45;H,F,F,H,H,H,H,-,-,-],[B50;L45;H,Cl,Cl,H,H,H,H,-,-,-],[B51;L45;H,H,H,H,H,H,H,-,-,-],[B52;L45;H,H,H,F,F,H,H,-,-,-],[B53;L45;H,H,H,Me,Me,H,H,-,-,-],[B54;L45;H,H,H,Cl,Cl,H,H,-,-,-],[B55;L45;H,H,H,H,H,Me,Me,-,-,-],[B56;L45;H,H,H,H,H,Cl,Cl,-,-,-],[B57;L45;H,H,H,H,H,F,F,-,-,-],[B58;L46;H,H,H,H,H,H,H,H,H,-],[B59;L46;Me,H,H,H,H,H,H,H,H,-],[B60;L46;F,H,H,H,H,H,H,H,H,-],[B61;L46;Cl,H,H,H,H,H,H,H,H,-],[B62;L46;H,F,F,H,H,H,H,H,H,-],[B63;L46;H,Cl,Cl,H,H,H,H,H,H,-],[B64;L46;H,Me,Me,H,H,H,H,H,H,-],[B65;L46;H,H,H,F,F,H,H,H,H,-],[B66;L46;H,H,H,Cl,Cl,H,H,H,H,-],[B67;L46;H,H,H,Me,Me,H,H,H,H,-],[B68;L46;H,H,H,H,H,F,F,H,H,-],[B69;L46;H,H,H,H,H,Cl,Cl,H,H,-],[B70;L46;H,H,H,H,H,Me,Me,H,H,-],[B71;L46;H,H,H,H,H,H,H,F,F,-],[B72;L46;H,H,H,H,H,H,H,Cl,Cl,-],[B73;L46;H,H,H,H,H,H,H,Me,Me,-],[B74;L47;H,H,H,H,H,H,H,H,-,-],[B75;L47;Me,H,H,H,H,H,H,H,-,-],[B76;L47;F,H,H,H,H,H,H,H,-,-],[B77;L47;Cl,H,H,H,H,H,H,H,-,-],[B78;L47;H,F,F,H,H,H,H,H,-,-],[B79;L47;H,Cl,Cl,H,H,H,H,H,-,-],[B80;L47;H,Me,Me,H,H,H,H,H,-,-],[B81;L47;H,H,H,F,F,H,H,H,-,-],[B82;L47;H,H,H,Cl,Cl,H,H,H,-,-],[B83;L47;H,H,H,Me,Me,H,H,H,-,-],[B84;L47;H,H,H,H,H,F,F,H,-,-],[B85;L47;H,H,H,H,H,Cl,Cl,H,-,-],[B86;L47;H,H,H,H,H,Me,Me,H,-,-],[B87;L47;F,H,H,H,H,H,H,F,-,-],[B88;L47;Cl,H,H,H,H,H,H,Cl,-,-],[B89;L47;Me,H,H,H,H,H,H,Me,-,-],[B90;L48;H,H,H,H,H,H,H,H,H,H],[B91;L48;Me,H,H,H,H,H,H,H,H,H],[B92;L48;F,H,H,H,H,H,H,H,H,H],[B93;L48;Cl,H,H,H,H,H,H,H,H,H],[B94;L48;H,F,F,H,H,H,H,H,H,H],[B95;L48;H,Cl,Cl,H,H,H,H,H,H,H],[B96;L48;H,Me,Me,H,H,H,H,H,H,H],[B97;L48;H,H,H,F,F,H,H,H,H,H],[B98;L48;H,H,H,Cl,Cl,H,H,H,H,H],[B99;L48;H,H,H,Me,Me,H,H,H,H,H],[B100;L48;H,H,H,H,H,F,F,H,H,H],[B101;L48;H,H,H,H,H,Cl,Cl,H,H,H],[B102;L48;H,H,H,H,H,Me,Me,H,H,H],[B103;L48;H,H,H,H,H,H,H,F,F,H],[B104;L48;H,H,H,H,H,H,H,Cl,Cl,H],[B105;L48;H,H,H,H,H,H,H,Me,Me,H],[B106;L48;F,H,H,H,H,H,H,H,H,F],[B107;L48;Cl,H,H,H,H,H,H,Me,Me,Cl],[B108;L48;Me,H,H,H,H,H,H,Me,Me,Me],[B109;L49;H,H,H,H,H,H,H,H,-,-],[B110;L49;Me,H,H,H,H,H,H,H,-,-],[B111;L49;F,H,H,H,H,H,H,H,-,-],[B112;L49;Cl,H,H,H,H,H,H,H,-,-],[B113;L49;H,F,F,H,H,H,H,H,-,-],[B114;L49;H,Cl,Cl,H,H,H,H,H,-,-],[B115;L49;H,Me,Me,H,H,H,H,H,-,-],[B116;L49;H,H,H,F,F,H,H,H,-,-],[B117;L49;H,H,H,Cl,Cl,H,H,H,-,-],[B118;L49;H,H,H,Me,Me,H,H,H,-,-],[B119;L49;H,H,H,H,H,F,F,H,-,-],[B120;L49;H,H,H,H,H,Cl,Cl,H,-,-],[B121;L49;H,H,H,H,H,Me,Me,H,-,-],[B122;L49;F,H,H,H,H,H,H,F,-,-],[B123;L49;Cl,H,H,H,H,H,H,Cl,-,-],[B124;L49;Me,H,H,H,H,H,H,Me,-,-],[B125;L50;H,H,H,H,H,H,H,H,H,H],[B126;L50;Me,H,H,H,H,H,H,H,H,H],[B127;L50;F,H,H,H,H,H,H,H,H,H],[B128;L50;Cl,H,H,H,H,H,H,H,H,H],[B129;L50;H,F,F,H,H,H,H,H,H,H],[B130;L50; H,Cl,Cl,H,H,H,H,H,H,H],[B131;L50;H,Me,Me,H,H,H,H,H,H,H],[B132;L5 0;H,H,H,F,F,H,H,H,H,H],[B133;L50;H,H,H,Cl,Cl,H,H,H,H,H],[B134;L5 0;H,H,H,Me,Me,H,H,H,H,H],[B135;L50;H,H,H,H,H,F,F,H,H,H],[B136;L5 0;H,H,H,H,H,Cl,Cl,H,H,H],[B137;L50;H,H,H,H,H,Me,Me,H,H,H],[B138; L50;H,H,H,H,H,H,H,F,F,H],[B139;L50;H,H,H,H,H,H,H,Cl,Cl,H],[B140; L50;H,H,H,H,H,H,H,Me,Me,H],[B141;L50;F,H,H,H,H,H,H,H,H,F],[B142; L50;Cl,H,H,H,H,H,H,Me,Me,Cl],[B143;L50;Me,H,H,H,H,H,H,Me,Me,Me]. In compound (A-2), A; x However, it is a 1,2,3-triazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX40). In compound (A-2), A x However, it is a 4-methyl-1,2,3-triazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented byY1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX41). In compound (A-2), A x However, it is a 4,5-dimethyl-1,2,3-triazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX42). In compound (A-2), A x However, it is a tetrazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX43). In compound (A-2), A x However, it is a 5-methyl-tetrazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent xsubstituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX44). In compound (A-2), A x However, it is an isothiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX45). In compound (A-2), A x However, it is an isoxazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX46). In compound (A-2), A x However, it is a 5-methyl-isothiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent xsubstituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX47). In compound (A-2), A x However, it is a 5-methyl-isoxazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX48). In compound (A-2), A x However, it is an oxazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX49). In compound (A-2), A x However, it is an oxazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent xsubstituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX50). In compound (A-2), A x However, it is a thiazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX51). In compound (A-2), A x However, it is a 4-methyl-oxazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX52). In compound (A-2), A x However, it is a 4-methyl-thiazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent xsubstituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX53). In compound (A-2), A x However, it is a 5-methyl-oxazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX54). In compound (A-2), A x However, it is a 5-methyl-thiazole-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX55). In compound (A-2), A x However, it is a 1,2,4-oxadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that representx substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX56). In compound (A-2), A x However, it is a 1,2,4-thiadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX57). In compound (A-2), A x However, it is a 5-methyl-1,2,4-oxadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX58). In compound (A-2), A x However, it is a 5-methyl-1,2,4-thiadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, Lx The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX59). In compound (A-2), A x However, it is a 5-ethyl-1,2,4-oxadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX60). In compound (A-2), A x However, it is a 5-ethyl-1,2,4-thiadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX61). In compound (A-2), A x However, it is a 5-cyclopropyl-1,2,4-oxadiazole-3-yl group, R 1x, and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX62). In compound (A-2), A x However, it is a 5-cyclopropyl-1,2,4-thiazadiazole-3-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX63). In compound (A-2), A x However, it is a pyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX64). In compound (A-2), A x However, it is a pyridazine-3-yl group, R 1x, and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX65). In compound (A-2), A x However, it is a pyrimidine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX66). In compound (A-2), A x However, it is a pyrimidine-4-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX67). In compound (A-2), A x However, it is a pyrazine-2-yl group, R 1x , and R 2xis a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX68). In compound (A-2), A x However, it is a 3-methylpyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX69). In compound (A-2), A x However, it is a 3-chloropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX70). In compound (A-2), A x However, it is a 3-fluoropyridine-2-yl group, R 1x , and R 2xis a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX71). In compound (A-2), A x However, it is a 4-methylpyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX72). In compound (A-2), A x However, it is a 4-chloropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX73). In compound (A-2), A x However, it is a 4-fluoropyridine-2-yl group, R 1x , and R 2xis a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX74). In compound (A-2), A x However, it is a 5-methylpyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX75). In compound (A-2), A x However, it is a 5-chloropyridine-2-yl group, R 1x , and R 2x is a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in combination B (hereinafter referred to as compound group SX76). In compound (A-2), A x However, it is a 5-fluoropyridine-2-yl group, R 1x , and R 2xis a hydrogen atom, L x The base and L that represent x substituent R in the group represented by Y1 , R Y2 , R Y3 , R Y4 , R Y5 , R Y6 , R Y7 , R Y8 , R Y9 , and R Y10 A compound whose combination is one of the combinations listed in Combination B (hereinafter referred to as Compound Group SX77).
[0090] The following are examples of formulations. Note that "parts" refers to parts by weight. Furthermore, compound S represents a compound listed in compound group SX1 to SX77.
[0091] Formulation Example 1 A formulation is obtained by mixing 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of any one of the compounds S, and 55 parts of water, and then finely grinding the mixture by a wet grinding method.
[0092] Formulation Example 2 A formulation is obtained by grinding and mixing 50 parts of any one of the compounds S, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica.
[0093] Formulation Example 3 A formulation is obtained by mixing 5 parts of any one of the compounds S, 9 parts of polyoxyethylene styrylphenyl ether, 5 parts of polyoxyethylene decyl ether (ethylene oxide addition number: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.
[0094] Formulation Example 4 Two parts of any one of the compounds S, one part of silica, two parts of calcium ligninsulfonate, thirty parts of bentonite, and sixty-five parts of kaolin clay are crushed and mixed, an appropriate amount of water is added and kneaded, granulated in a granulator, and then dried to obtain a formulation.
[0095] Formulation Example 5 Ten parts of any one of the compounds S are mixed with a mixture of 18 parts benzyl alcohol and 9 parts DMSO. 6.3 parts GERONOL® TE250, 2.7 parts Ethylan® NS-500LQ, and 54 parts solvent naphtha are added and mixed to obtain a formulation.
[0096] Next, we will show some test examples. In Test Example 15, "untreated" means that the test was conducted under the same conditions as described in the test example, except that DMSO was dispensed instead of the DMSO dilution containing the compound. Similarly, in Test Example 7, "untreated leaf disc" means that the leaf disc was treated under the same conditions as described in the test example, except that DMSO was dispensed instead of the DMSO dilution containing the compound. Furthermore, in Test Example 11, "untreated" means that the aqueous dilution of the formulation containing the compound was not sprayed.
[0097] Test Example 1: Control Test against Septoria tritici (wheat leaf blight fungus) The compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into each well of a microtiter plate (96 wells). Then, 150 μL of YBG medium (Yeast bacto glycerol medium) pre-inoculated with wheat leaf blight fungus spores was dispensed into each well. This plate was cultured at 18°C for 3 days to allow the wheat leaf blight fungus to grow. After that, the absorbance at 550 nm in each well of the microtiter plate was measured, and this value was taken as the growth stage of the wheat leaf blight fungus. As a result, the compound showed efficacy in controlling plant diseases.
[0098] Test Example 2: Control Test against Ustilago maydis (corn smut virus). The compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into each well of a microtiter plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium), which had been pre-inoculated with stilago maydis spores, was dispensed into each well. This plate was incubated at 18°C for 4 days to allow the stilago maydis to grow. After that, the absorbance at 550 nm in each well of the microtiter plate was measured, and this value was taken as the growth stage of the stilago maydis. As a result, the compound showed efficacy in controlling plant diseases.
[0099] Test Example 3: Control Test against Rhynchosporium secalis (barley cloud mold fungus) The compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into each well of a microtiter plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium), which had been pre-inoculated with barley cloud mold fungus spores, was dispensed into each well. This plate was cultured at 18°C for 7 days to allow the barley cloud mold fungus to grow. After that, the absorbance at 550 nm in each well of the microtiter plate was measured, and this value was taken as the growth stage of the barley cloud mold fungus. As a result, the compound showed efficacy in controlling plant diseases.
[0100] Test Example 4: Control Test against Cucumber Gray Mold (Botrytis cinerea) The compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into each well of a microtiter plate (96 wells). Then, 150 μL of complete medium pre-inoculated with cucumber gray mold spores was dispensed into each well. The plate was cultured at 18°C for 4 days to allow the cucumber gray mold to grow. After that, the absorbance at 550 nm in each well of the microtiter plate was measured, and this value was taken as the growth rate of the cucumber gray mold. As a result, the compound showed efficacy in controlling plant diseases.
[0101] Test Example 5: Control Test against Peach Scratch Virus (Cladosporium carpophilum) Each well of the compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into each well of a microtiter plate (96 wells). Then, 150 μL of potato decoction liquid medium (PDB medium) pre-inoculated with peach scratch virus spores was dispensed into each well. This plate was cultured at 18°C for 5 days to allow the peach scratch virus to grow. After that, the absorbance at 550 nm in each well of the microtiter plate was measured, and this value was taken as the growth stage of the peach scratch virus. As a result, the compound showed efficacy in controlling plant diseases.
[0102] Test Example 6: Control Test against Cochliobolus miyabeanus (rice leaf spot disease fungus) The compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into each well of a microtiter plate (96 wells). Then, 150 μL of YBA medium (Yeast bacto acetate medium) pre-inoculated with spores of Cochliobolus miyabeanus was dispensed into each well. The plate was cultured at 23°C for 3 days to allow the Cochliobolus miyabeanus to grow. After that, the absorbance at 550 nm in each well of the microtiter plate was measured, and this value was taken as the growth stage of the Cochliobolus miyabeanus. As a result, the compound showed efficacy in controlling plant diseases.
[0103] Test Example 7 Control Test for Soybean Rust Disease (Phakopsora pachyrhizi) Leaf discs were prepared by cutting the true leaves of soybeans (variety: Kurosenkoku) to a diameter of 1 cm. 1 mL of agar medium (agar concentration 1.2%) was dispensed into each well of a 24-well microplate, and one leaf disc was placed on top of the agar medium in each well. A mixture of 0.5 μL of Solpol® 1200KX, 4.5 μL of DMSO, and 5 μL of xylene was mixed with 20 μL of DMSO solution containing 10,000 ppm of the test compound. The resulting mixture was diluted with deionized water to prepare a mixture containing the test compound at a predetermined concentration. 10 μL of the resulting mixture was sprayed onto each leaf disc. One day later, an aqueous suspension of spores of the soybean rust fungus (Phakopsora pachyrhizi) having the F129L amino acid substitution in the mitochondrial cytochrome b protein was spray-inoculated onto leaf discs. After inoculation, the microplates were placed in an artificial climate chamber (6 hours on, 18 hours off, temperature 23°C, humidity 60%). One day later, the leaf discs were air-dried until all water droplets on the surface were gone, and the microplates were placed again in the artificial climate chamber for 12 days. Subsequently, the area of soybean rust lesions was investigated. As a result, the lesion area of leaf discs treated with any one of the test compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 18 at a predetermined concentration of 200 ppm was 30% or less of the lesion area of untreated leaf discs.
[0104] Test Example 8: Control Test for Barley Net Spot Disease (Pyrenophora teres) Soil was packed into plastic pots, and barley (variety: Nishinohoshi) was sown in them and cultivated in a greenhouse for 7 days. The compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed onto the leaves of the barley so that it adhered well to the leaves. After spraying, the barley was air-dried, and one day later, an aqueous suspension of barley net spot fungus spores was spray-inoculated. After inoculation, the barley was placed in a greenhouse at 23°C during the day and 20°C at night under high humidity for 3 days, and then cultivated in the greenhouse for 7 days, after which the area of disease lesions was investigated. As a result, the compound showed efficacy in controlling plant diseases.
[0105] Test Example 9 Control Test for Wheat Rust (Puccinia recondita) Soil was packed into plastic pots, and wheat (variety: Shirogane) was sown therein and cultivated in a greenhouse for 9 days. The compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed onto the leaves of the wheat so that it adhered well to the leaves. After spraying, the wheat was air-dried and cultivated at 20°C under lighting for 5 to 7 days, after which wheat rust fungus spores were sprinkled on and inoculated. After inoculation, the wheat was placed at 23°C in the dark and humid for 1 day, then cultivated at 20°C under lighting for 8 days, and the area of disease lesions was investigated. As a result, the compound showed an effect in controlling plant diseases.
[0106] Test Example 10 Control Test for Wheat Leaf Blight (Septoria tritici) Soil was packed into plastic pots, and wheat (variety: Apogee) was sown and cultivated in a greenhouse for 10 days. The compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed onto the leaves of the wheat so that it adhered well to the leaves. After spraying, the wheat was air-dried, and 4 days later, an aqueous suspension containing spores of the wheat leaf blight fungus was spray-inoculated. After inoculation, the wheat was placed at 18°C and high humidity for 3 days, and then cultivated under light for 14 to 18 days, after which the area of lesions was investigated. As a result, the compound showed an effect in controlling plant diseases.
[0107] Test Example 11 Control Test for Soybean Rust Disease (Phakopsora pachyrhizi) Soil was packed into plastic pots, and soybeans (variety: Kurosenkoku) were sown therein and cultivated in a greenhouse for 10 to 14 days. Compounds 1, 2, 3, 8, 9, 10, 11, or 12, formulated according to the method described in Formulation Example 1, were mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed onto the leaves of the soybeans so that it adhered well to the leaves. After spraying, the soybeans were air-dried, and 2 to 5 days later, an aqueous suspension of soybean rust fungal spores was spray-inoculated. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under high humidity for 1 to 2 days, and then cultivated in the greenhouse for 12 days, after which the lesion area was investigated. As a result, the lesion area in soybeans treated with each of the above compounds was 30% or less of the lesion area in untreated soybeans.
[0108] Test Example 12: Control Test for Soybean Rust Disease (Phakopsora pachyrhizi) Soil was packed into plastic pots, sowed soybeans (variety: Kurosenkoku), and cultivated in a greenhouse for 10 days. The soybeans were then spray-inoculated with an aqueous suspension containing spores of the soybean rust fungus. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under high humidity for one day. Next, they were cultivated in the greenhouse for two days. Then, the compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed onto the leaves of the soybeans to ensure sufficient adhesion. After spraying, the soybeans were air-dried and cultivated in a greenhouse for eight days, after which the area of disease lesions was investigated. As a result, the compound showed efficacy in controlling plant diseases.
[0109] Test Example 13: Control Test for Soybean Leaf Spot Disease (Cercospora sojina) Soil was packed into plastic pots, and soybeans (variety: Tachinagaha) were sown and cultivated in a greenhouse for 13 days. The compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed onto the leaves of the soybeans so that it adhered well to the leaves. After spraying, the soybeans were air-dried, and one day later, an aqueous suspension of soybean leaf spot fungus spores was spray-inoculated. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under high humidity for 3 days, and then cultivated in the greenhouse for 16 days, after which the area of disease lesions was investigated. As a result, the compound showed an effect in controlling plant diseases.
[0110] Test Example 14: Control Test for Tomato Ring Spot Disease (Alternaria solani) Soil was packed into plastic pots, and tomatoes (variety: Patio) were sown and cultivated in a greenhouse for 20 days. The compound, formulated according to the method described in Formulation Example 1, was mixed with water to a concentration of 200 ppm, and the resulting mixture was sprayed onto the leaves of the tomatoes to ensure sufficient adhesion. After spraying, the tomatoes were air-dried, and one day later, an aqueous suspension of tomato ring spot fungal spores was spray-inoculated. After inoculation, the tomatoes were placed at 18°C and high humidity for 6 days, and then the area of lesions was examined. As a result, the compound showed efficacy in controlling plant diseases.
[0111] Test Example 15 Control Test against Soybean Rust Fungus (Phakopsora pachyrhizi) The test compound was diluted with DMSO to a concentration of 150 ppm, and 1 μL was dispensed into each well of a microtiter plate (96 wells). Then, 149 μL of an aqueous suspension of soybean rust fungus spores, in which soybean rust fungus spores had been pre-suspended, was dispensed into each well. After culturing this plate at 23°C for several hours, the number of germinated soybean rust fungus spores was counted. As a result, at a treatment concentration of 1 ppm, the number of germinated spores in wells containing any one of the test compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 was 50% or less of the number of germinated spores in the untreated wells.
[0112] Test Example 16: Control test against soybean rust fungus (Phakopsora pachyrhizi). The test was conducted using the present compound as the test compound at a treatment concentration of 10 ppm, following the same method as in Test Example 15. The results showed that the present compound exhibits efficacy in controlling plant diseases.
[0113] Test Example 17: Control test against soybean rust fungus (Phakopsora pachyrhizi). The test was conducted using the same method as in Test Example 15, with a treatment concentration of 0.016 ppm, and using this compound as the test compound. As a result, this compound showed efficacy in controlling plant diseases.
[0114] This compound has a control effect against plant diseases and can be used for plant disease control.
Claims
1. Formula (I) [wherein, A and Z 1 , G1 , 1 , L1 , 2 in combination, A is a group represented by A1, a group represented by A2, a group represented by A3, or a group represented by A4, and Z 1 is a phenyl group, a 5- or 6-membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazol-3-yl group) {the phenyl group and the 5- or 6-membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazol-3-yl group) may be substituted with one or more substituents selected from Group A}, a C3-C6 alicyclic hydrocarbon group, a 3- to 6-membered non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3- to 6-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B}, OR 3 , SR 4 , S(O)R 5 , or S(O)2R 6 in combination; or A is a group represented by A5, and Z 1 is a 5- or 6-membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazol-3-yl group) {the 5- or 6-membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazol-3-yl group) may be substituted with one or more substituents selected from Group A}, a C3-C6 alicyclic hydrocarbon group, a 3- to 6-membered non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3- to 6-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B}, OR 7 , SR 8 , S(O)R 9 , or S(O)2R 10 in combination, and the group represented by A1, the group represented by A2, the group represented by A3, the group represented by A4, and the group represented by A5 are each a group represented by the following formula (* represents the bonding site with CR 1 R 2 ), Q 1 , and Q 2 are the same or different and represent an oxygen atom or a sulfur atom, L 1 represents an oxygen atom, a sulfur atom, or NR L1 , G 1 represents a nitrogen atom or CR G1 represents, G 2 is a nitrogen atom or CR G2 This represents G 3 is a nitrogen atom or CR G3 This represents G 4 is a nitrogen atom or CR G4 This represents G 5 is a nitrogen atom or CR G5 This represents (however, G 2 G 3 G 4 , and G 5 (Of which, the number of nitrogen atoms is 0 or 1), R 1 and R 2 These are a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, or a 3-8 membered non-aromatic heterocyclic group, which may be the same or different and substituted with one or more substituents selected from group C {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group D}, OR 17 , NR 18 R 19 R represents a halogen atom or a hydrogen atom. 17 R represents a C1-C6 chain hydrocarbon group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group (the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group may be substituted with one or more substituents selected from group F), or a hydrogen atom. 18 and R 19 R represents a C1-C6 chain hydrocarbon group, which may be the same or different in phase and may be substituted with one or more halogen atoms, or a hydrogen atom. 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 R represents a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group D, either identical or different. 11 , R 12 , R 14 , R 15 , R 16 , R G1 , R G2 , R G3 , R G4 and R G5 R represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group C, a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group B, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom, and R 13 R represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group E, a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group B, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom. L1 This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group C, a C3-C6 alicyclic hydrocarbon group which may be substituted with one or more substituents selected from group B, a cyano group, or a hydrogen atom. Group A: A group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, a C3-C6 alicyclic hydrocarbon group, a 3-6 membered non-aromatic heterocyclic group {the C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from group D}, a halogen atom, a cyano group, a nitro group, a sulfanyl group, and a hydroxyl group. Group B: A group consisting of oxo groups, thioxo groups, methyl groups, C2-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups {the C2-C6 chain hydrocarbon groups, the C1-C6 alkoxy groups, the C1-C6 alkylamino groups, and the C2-C8 dialkylamino groups may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups {the C3-C6 alicyclic hydrocarbon groups and the 3-6 membered non-aromatic heterocyclic groups may be substituted with one or more substituents selected from Group D}, halogen atoms, cyano groups, nitro groups, sulfanyl groups, and hydroxyl groups. Group C: A group consisting of C1-C6 alkoxy groups, C3-C6 alicyclic hydrocarbon groups, 3-6 membered non-aromatic heterocyclic groups (the C3-C6 alicyclic hydrocarbon groups and the 3-6 membered non-aromatic heterocyclic groups may be substituted with one or more substituents selected from Group D), halogen atoms, cyano groups, nitro groups, and hydroxyl groups. Group D: A group consisting of oxo groups, thioxo groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups (the C1-C6 chain hydrocarbon groups and the C1-C6 alkoxy groups may be substituted with one or more halogen atoms), hydroxyl groups, halogen atoms, and cyano groups.A method for controlling plant diseases comprising treating a compound represented by Group E, or its N oxide, or a salt thereof, on a plant or the soil on which the plant is cultivated, with a compound represented by Group D, or its N oxide, or a salt thereof.
2. Formula (II) [In the formula, A a and Z a The combination is A a A2 a The base shown is A3 a The base indicated by, or A4 a The group is represented by Z a However, group G a A phenyl group, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) which may be substituted with one or more substituents selected from group A. a Group F a Cyclopropyl groups substituted with one or more more selected substituents, Group B a A C5-C6 alicyclic hydrocarbon group, or OR, which may be substituted with one or more more selected substituents. 3a The combination is A a is A5 a The group is represented by Z a However, a 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) {The 5-6 membered aromatic heterocyclic group (excluding the 1,2,4-oxadiazole-3-yl group and the pyrrole-1-yl group) belongs to group A a Group F a Cyclopropyl groups substituted with one or more more selected substituents, Group B a A C5-C6 cycloalkenyl group which may be substituted with one or more more selected substituents, OR 4a This represents the combination, A2 a The base shown is A3 a The base shown is A4 a The base shown by, and A5 a The groups shown by are the groups shown in the following formula (# is CR) 1a R 2a (represents the bonding site with) Q 2a and L 1a is the same or different and represents an oxygen atom or a sulfur atom, and G 1a represents a nitrogen atom or CR G1a and G 2a represents a nitrogen atom or CR G2a and G 3a represents a nitrogen atom or CR G3a and G 4a represents a nitrogen atom or CR G4a and G 5a represents a nitrogen atom or CR G5a and represents (however, among G 2a , G 3a , G 4a , and G 5a , the number of nitrogen atoms is 0 or 1), R 1a and R 2a are the same or different and may be substituted with one or more substituents selected from group C a a C₁-C₄ chain hydrocarbon group, a C₃-C₆ alicyclic hydrocarbon group, or a 3- to 5-member non-aromatic heterocyclic group {the C₃-C₆ alicyclic hydrocarbon group and the 3- to 5-member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group D a}, OR 10a , a halogen atom, or a hydrogen atom, and R 10a may be substituted with one or more substituents selected from group H a a C₁-C₆ chain hydrocarbon group, a (C₁-C₆ alkyl)carbonyl group that may be substituted with one or more halogen atoms, or a hydrogen atom, and R 3a and R 4a are the same or different and represent a C₄-C₆ alicyclic hydrocarbon group that may be substituted with one or more substituents selected from group D a , and R 6a , R 8a , R 9a , R G1a , R G2a , R G4a and R G5a are the same or different and may be substituted with one or more substituents selected from group E a a C₁-C₄ chain hydrocarbon group, group B a R represents a C3-C4 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom, which may be substituted with one or more more selected substituents. 7a is group E a C1-C3 chain hydrocarbon groups, group B, which may be substituted with one or more more selected substituents. a R represents a C3-C4 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, a halogen atom, a hydroxyl group, or a hydrogen atom, which may be substituted with one or more more selected substituents. G3a This refers to C1-C4 chain hydrocarbon groups, group B. a This represents a C3-C4 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a nitro group, a halogen atom, or a hydrogen atom, which may be substituted with one or more more selected substituents. Group A a : Methyl group, CFH2 group, CF2H group, C2-C6 chain hydrocarbon group, C1-C6 alkoxy group {The C2-C6 chain hydrocarbon group and the C1-C6 alkoxy group may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon group, 3-6 membered non-aromatic heterocyclic group {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group D a Group B: A group consisting of halogen atoms, cyano groups, nitro groups, and sulfanyl groups, which may be substituted with one or more more selected substituents. a : Oxo group, thioxo group, C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C8 dialkylamino group, {The C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon group, 3-6 membered non-aromatic heterocyclic group {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group D a A group consisting of halogen atoms, cyano groups, nitro groups, hydroxyl groups, and sulfanyl groups, which may be substituted with one or more more selected substituents. Group C a : A C1-C6 alkoxy group, a C3-C6 alicyclic hydrocarbon group, or a 3-6 membered non-aromatic heterocyclic group which may be substituted with one or more halogen atoms {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group D a A group consisting of halogen atoms, cyano groups, nitro groups, and hydroxyl groups, which may be substituted with one or more more selected substituents. Group D a : A group consisting of an oxo group, a thioxo group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, {the C1-C6 chain hydrocarbon group and the C1-C6 alkoxy group may be substituted with one or more halogen atoms}, a hydroxyl group, a halogen atom, and a cyano group. Group E a : A C1-C6 alkoxy group which may be substituted with one or more halogen atoms, and a C3-C6 alicyclic hydrocarbon group {The C3-C6 alicyclic hydrocarbon group is from group D a A group consisting of {which may be substituted with one or more substituents selected from}. Group F a : A group consisting of C1-C6 chain hydrocarbon groups, C3-C6 alicyclic hydrocarbon groups, cyano groups, and halogen atoms, which may be substituted with one or more halogen atoms. Group G a : C1-C6 chain hydrocarbon group, C2-C6 alkoxy group {The C1-C6 chain hydrocarbon group and the C2-C6 alkoxy group may be substituted with one or more halogen atoms}, C3-C6 alicyclic hydrocarbon group, 3-6 membered non-aromatic heterocyclic group {The C3-C6 alicyclic hydrocarbon group and the 3-6 membered non-aromatic heterocyclic group belong to group D a A group consisting of halogen atoms, cyano groups, nitro groups, and hydroxyl groups, which may be substituted with one or more more selected substituents. Group H a Compounds represented by : a group consisting of a phenyl group which may be substituted with one or more halogen atoms, and halogen atoms, or their N oxides or salts thereof.
3. A a A2 a It is a base represented by Q 2a The compound according to claim 2, or its N oxide, or a salt thereof, wherein is an oxygen atom.
4. A a A4 a The group shown is G 1a The compound according to claim 2, or its N oxide, or a salt thereof, wherein the compound is CH.
5. A composition containing the compound described in any of claims 2 to 4, its N oxide, or a salt thereof, and an inert carrier.
6. A composition containing one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and a compound or its N oxide or a salt thereof as described in any of claims 2 to 4: Group (a): A group consisting of insecticidal components, acaricidal components, and nematicidal components; Group (b): A bactericidal component; Group (c): A plant growth regulating component; Group (d): A repellent component.
7. A method for controlling plant diseases, comprising treating a plant or soil on which a plant is cultivated with an effective amount of a compound according to any one of claims 2 to 4, its N oxide, or a salt thereof, or an effective amount of the composition according to claim 6.
8. Use of a compound according to any one of claims 2 to 4, its N oxide, or a salt thereof, or the composition according to claim 6, for the control of plant diseases.
9. Seeds or vegetative reproductive organs containing an effective amount of the compound according to any one of claims 2 to 4, its N oxide, or a salt thereof, or an effective amount of the composition according to claim 6.