WO2022181793A1 - フェニル酢酸誘導体、その用途及びその製造中間体 - Google Patents
フェニル酢酸誘導体、その用途及びその製造中間体 Download PDFInfo
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- WO2022181793A1 WO2022181793A1 PCT/JP2022/008031 JP2022008031W WO2022181793A1 WO 2022181793 A1 WO2022181793 A1 WO 2022181793A1 JP 2022008031 W JP2022008031 W JP 2022008031W WO 2022181793 A1 WO2022181793 A1 WO 2022181793A1
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
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- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds only one oxygen atom attached to the nitrogen atom
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- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
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- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
- C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
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Definitions
- Patent Document 1 describes a phenylacetic acid derivative.
- the purpose of the present invention is to provide a compound that has excellent control efficacy against pests.
- R 8 and R 9 are the same or different, a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group G, substituted with one or more substituents selected from group E C3-C6 cycloalkyl group optionally substituted, phenyl group, 5-6 membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6 membered aromatic heterocyclic group are substituted with one or more groups selected from group F group], or represents a hydrogen atom
- R 10 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group G, C3-C6 optionally substituted with one or more substituents selected from group E A cycloalkyl group, a phenyl group, or a 5- to 6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group F good ⁇
- R 11 represents a C
- Group D C1-C6 alkoxy group, C1-C6 alkylthio group ⁇ the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from group G ⁇ , C3 -C6 cycloalkyl group, 3-8 membered non-aromatic heterocyclic group ⁇ the C3-C6 cycloalkyl group and the 3-8 membered non-aromatic heterocyclic group are substituted with one or more substituents selected from group E ⁇ , a C6-C10 aryl group,
- Group F C1-C3 chain hydrocarbon group, C3-C6 cycloalkyl group, C1-C3 alkoxy group, C1-C3 alkylthio group ⁇ said C1-C3 chain hydrocarbon group, said C3-C6 cycloalkyl group, said The C1-C3 alkoxy group and said C1-C3 alkylthio group may be substituted with one or more substituents selected from group G ⁇ , a group consisting of a halogen atom, a cyano group, a nitro group and a hydroxy group.
- Group G a group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group and a halogen atom.
- the compound represented by hereinafter referred to as the compound N of the present invention), or its N oxide or a salt thereof (hereinafter, the compound represented by formula (I), or its N oxide or a salt thereof is referred to as the compound of the present invention ).
- n is 1; R 1 and R 2 are the same or different and are a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom; R 2 is attached to the 4- or 5-position, E is a phenyl group, a 5- to 6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group H ⁇ , R 3 —O—N ⁇ C(R 4 )—, R 5 —C ⁇ C—, R 6 O—, or a C5-C6 cycloalkenyl group, R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group G, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or R 7 CH 2 —, R 4 is a C1-
- Group H C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, C1-C3 alkoxy group, trifluoromethoxy group, C3-C4 cycloalkyl group, halogen atom, cyano group, and nitro A group consisting of groups.
- Group I consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a phenyl group ⁇ the C1-C3 alkoxy group and the phenyl group may be substituted with one or more halogen atoms ⁇ , and a halogen atom group.
- Group J a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group ⁇ the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms ⁇ , the group consisting of C3-C6 cycloalkyl groups, halogen atoms, cyano groups and nitro groups;
- E is a phenyl group, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group ⁇ the phenyl group, the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group are one or more selected from Group H ], R 5 —C ⁇ C—, R 6 O—, or a C5-C6 cycloalkenyl group, the compound according to [2] or its N oxide, or a salt thereof .
- a seed or vegetative reproductive organ containing an effective amount of the compound according to any one of [1] to [3] or its N oxide or salt thereof, or an effective amount of the composition according to [5] .
- Formula (II): [In the formula, The combination of X and L is a combination in which X is a nitrogen atom and L is an oxygen atom or NH; or represents a combination in which X is CH and L is an oxygen atom; E a is R 12a C(O)—, R 12a C( N—OH)—, hydroxy group, B(OH) 2 , 4,4,5,5-tetramethyl-1,3,2-dioxaborolane -2-yl group, or represents a halogen atom, R 1a and R 2a are the same or different and represent a methyl group or a halogen atom; R 12a represents a C1-C3 alkyl group or a hydrogen atom.
- a halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
- a substituent is substituted with two or more halogen atoms, each of those halogen atoms may be the same or different.
- substituent is substituted with two or more groups or atoms selected from a specific group (for example, the group consisting of C1-C3 alkyl groups and halogen atoms), each of these groups or atoms may be the same or different.
- substituents selected from group X may be any of A, B, C, D, E, F, G, H, I, J, and K or one
- substituents may be the same or different.
- CX-CY used herein means that the number of carbon atoms is from X to Y.
- C1-C6 means 1 to 6 carbon atoms.
- a chain hydrocarbon group represents an alkyl group, an alkenyl group or an alkynyl group.
- alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, A hexyl group and a decyl group are included.
- alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3- butenyl, 4-pentenyl, 5-hexenyl, and 9-decenyl groups.
- alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, 5 -hexynyl group and 9-decynyl group.
- Alkoxy groups include, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups.
- alkylthio groups include methylthio, ethylthio, propylthio, isopropylthio, butylthio, tert-butylthio, pentylthio, and hexylthio groups.
- Cycloalkyl groups include, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.
- Cycloalkenyl groups include, for example, cyclopentenyl and cyclohexenyl groups.
- Aryl groups include, for example, phenyl, indenyl, indanyl, naphthyl, and tetrahydronaphthyl groups.
- aromatic heterocyclic groups include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, and pyridyl groups.
- pyridazinyl pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, indazolyl, benzimidazolyl, imidazopyridyl, benzothiophenyl, benzofuranyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl. be done.
- a soybean rust fungus having an F129L amino acid substitution in the mitochondrial cytochrome b protein has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein, and as a result of the mutation, the F129L amino acid substitution occurs, resulting in QoI It is a fungicide-resistant soybean rust fungus (scientific name: Phakopsora pachyrhizi).
- Stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
- the present invention includes each stereoisomer and mixtures of stereoisomers in any proportion.
- Geometric isomers include, for example, the following structures.
- Compound N of the present invention or its N oxide can be mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid and benzoic acid to obtain hydrochloride, sulfate, nitrate, phosphate, acetate and benzoate. may form an acid addition salt such as
- Embodiments of the compound N of the present invention include the following compounds.
- a compound N in which E is R 3 —ON C(R 4 )— in the compound N of the present invention.
- R 3 is a C1-C6 chain hydrocarbon group ⁇ the C1-C6 chain hydrocarbon group is one or more selected from the group consisting of a C3-C4 cycloalkyl group and a halogen atom; optionally substituted with a substituent ⁇ , or R 7 CH 2 —, R 4 is a methyl group or a hydrogen atom, R 7 is a phenyl group or a 5- to 6-membered aromatic heterocyclic group ⁇ the The phenyl group and the 5- to 6-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group K ⁇ .
- Group K a group consisting of a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms and a halogen atom.
- R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
- E is a phenyl group optionally substituted with one or more substituents selected from group A;
- E is a 5- to 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group B;
- Aspect 10 In the compound N of the present invention, E is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H.
- E is a pyridyl group, a thienyl group, a thiazolyl group, or a pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group are selected from Group H 1 optionally substituted with any of the above substituents ⁇ .
- E is a pyridyl group, a thienyl group, a thiazolyl group, or a pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group are selected from group K 1 optionally substituted with any of the above substituents ⁇ .
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , a C5-C6 cycloalkenyl group, R 3 —O —N ⁇ C(R 4 )—, R 5 —C ⁇ C—, or R 6 O—, and R 3 is a C1-C6 chain hydrocarbon group ⁇ the C1-C6 chain hydrocarbon group is optionally substituted with one or more substituents selected from the group consisting of a C3-C4 cycloalkyl group and a halogen atom ⁇ , or R 7 CH 2 —, R
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , a 5- or 6-membered aromatic heterocyclic group ⁇
- the 5- to 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H ⁇ , C3- optionally substituted with one or more substituents selected from group C C7 cycloalkenyl group, R 5 —C ⁇ C—, or R 6 O—
- R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group ⁇ the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms ⁇ .
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , a C5-C6 cycloalkenyl group, R 5 -C ⁇ C— or R 6 O—, R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 6 is substituted with one or more substituents selected from group I
- E is
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl a group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , R 5 —C ⁇ C—, or R 6 O—, R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 6 is C2- optionally substituted with one or more substituents selected from group I A compound that is a C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , a 5- or 6-membered aromatic heterocyclic group ⁇
- the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group H ⁇ , or R 5 -C ⁇ C-, where R 5 is a C1-C6 chain Formula hydrocarbon group or C3-C6 cycloalkyl group ⁇ the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms ⁇ .
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl a group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , or R -C ⁇ C- , A compound in which R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , a 5- or 6-membered aromatic heterocyclic group ⁇ The 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group H ⁇ , or a compound represented by R 6 O-.
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl a group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , or R 6 O—, and R 6 is , a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from Group A ⁇ , R 5 —C ⁇ C—, or R 6 O— and R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group ⁇ the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group are one or more halogen atoms optionally substituted with ⁇ .
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , R 5 —C ⁇ C—, or R 6 O—, R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 6 is C2 optionally substituted with one or more substituents selected from group I - A compound that is a C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , or a 5- or 6-membered aromatic heterocyclic group. ⁇ The 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group H ⁇ .
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , a pyridyl group, a thienyl group, a thiazolyl group, or A compound which is a pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from group K ⁇ .
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from Group A ⁇ , or R 5 -C ⁇ C- , R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group ⁇ the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group are substituted with one or more halogen atoms; may ⁇ .
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from Group H ⁇ , or R 5 -C ⁇ C- , R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , or R 6 O—.
- E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , or R 6 O—, and R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
- Aspect 33 The compound according to Aspect 2, wherein X is CH and L is an oxygen atom.
- Aspect 34 The compound according to Aspect 3, wherein X is CH and L is an oxygen atom.
- Aspect 35 The compound according to Aspect 4, wherein X is CH and L is an oxygen atom.
- Aspect 36 The compound according to Aspect 5, wherein X is CH and L is an oxygen atom.
- Aspect 37 The compound according to Aspect 6, wherein X is CH and L is an oxygen atom.
- Aspect 38 The compound according to Aspect 7, wherein X is CH and L is an oxygen atom.
- Aspect 39 The compound according to Aspect 8, wherein X is CH and L is an oxygen atom.
- Aspect 40 The compound according to Aspect 9, wherein X is CH and L is an oxygen atom.
- R 1 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom. .
- R 1 is a methyl group, a methoxy group, or a halogen atom.
- R 2 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom. .
- R 2 is a methyl group, a methoxy group, or a halogen atom.
- R 1 and R 2 are the same or different and are a C1-C3 alkyl group optionally substituted with one or more halogen atoms, methoxy A compound that is a group or a halogen atom.
- R 1 is a methyl group, a methoxy group, or a halogen atom, and R 2 is substituted with one or more halogen atoms.
- R 1 is a methyl group
- R 2 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, methoxy A compound that is a group or a halogen atom.
- R 1 and R 2 are methyl groups.
- n is 1.
- Aspect 90 The compound according to Aspect 69, wherein n is 1 and R 2 is bonded to the 4-position.
- Aspect 94 The compound according to Aspect 73, wherein n is 1 and R 2 is bonded to the 4-position.
- n 1 and R 2 is bonded to the 4-position is represented by the formula (I-4) [In the formula, symbols have the same meanings as defined in [1]. ] is a compound represented by Compounds of embodiments 88-94 can also be represented by formula (I-4).
- the compound represented by formula (A1) (hereinafter referred to as compound (A1)) is a 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 and a base.
- E 1 is a C6-C10 aryl group or a 5- to 10-membered aromatic heterocyclic group ⁇ the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group are 1 selected from Group A optionally substituted with the above substituents ⁇ , and M 1 represents B(OH) 2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group , X 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a triflyloxy group, etc., and other symbols have the same meanings as above.
- the reaction is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), Ethers such as dimethoxyethane (hereinafter referred to as ethers); Halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); Dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone ( amides such 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) ); water and
- Palladium catalysts used in the reaction include tris(dibenzylideneacetone)dipalladium(0) (hereinafter referred to as Pd 2 (dba) 3 ), tetrakis(triphenylphosphine)palladium(0) (hereinafter referred to as Pd(PPh 3 ) 4 ), and ⁇ 1,1′-bis(diphenylphosphino)ferrocene ⁇ palladium(II) dichloride (hereinafter referred to as PdCl 2 (dppf)).
- Pd 2 (dba) 3 tris(dibenzylideneacetone)dipalladium(0)
- Pd(PPh 3 ) 4 tetrakis(triphenylphosphine)palladium(0)
- PdCl 2 (dppf) ⁇ 1,1′-bis(diphenylphosphino)ferrocene ⁇ palladium(II) dichloride
- bases used in the reaction 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 hydrogen carbonates such as sodium and potassium hydrogen carbonate (hereinafter referred to as alkali metal hydrogen carbonates); sodium fluoride and tripotassium phosphate.
- organic bases such as triethylamine and pyridine
- alkali metal carbonates such as sodium carbonate and potassium carbonate
- alkali metal hydrogen carbonates such as sodium and potassium hydrogen carbonate
- sodium fluoride and tripotassium phosphate sodium fluoride and tripotassium phosphate.
- a ligand may be used in the reaction, if necessary.
- Ligands used in the reaction include triphenylphosphine, xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2- dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane and the like.
- the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B1).
- the compound (M1) is usually used at a ratio of 1 to 10 mol
- the palladium catalyst is usually used at a ratio of 0.01 to 1 mol
- the base is usually used at a ratio of 1 to 10 mol, relative to 1 mol of the compound (B1).
- the reaction temperature is usually within the range of 0-150°C.
- the reaction time is usually within the range of 0.1 to 120 hours.
- compound (A1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M1) is known or can be produced according to known methods.
- Manufacturing method B Compound (A1) is prepared by reacting a compound represented by formula (B2) (hereinafter referred to as compound (B2)) and a compound represented by formula (M2) (hereinafter referred to as compound (M2)) with a palladium catalyst and a base. It can be produced by reacting in the presence. [In the formula, symbols have the same meanings as described above. ] The reaction can be carried out according to production method A using compound (M2) in place of compound (B1) and compound (B2) in place of compound (M1). Compound (M2) is known or can be produced according to known methods.
- the compound represented by the formula (A2) (hereinafter referred to as compound (A2)) is obtained by combining the compound (B1) and the compound represented by the formula (M3) (hereinafter referred to as compound (M3)) with a metal catalyst and a base. It can be produced by reacting in the presence.
- a metal catalyst and a base a metal catalyst and a base.
- the reaction is usually carried out in a solvent. Solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof.
- Metal catalysts used in the reaction include, for example, bis(triphenylphosphine)palladium(II) dichloride and copper(I) iodide.
- bases used in the reaction include organic bases.
- the compound (M3) is usually used at a ratio of 1 to 10 mol
- the metal catalyst is usually used at a ratio of 0.01 to 1 mol
- the base is usually used at a ratio of 1 to 10 mol, relative to 1 mol of the compound (B1). Used.
- the reaction temperature is usually within the range of 0-150°C.
- the reaction time is usually within the range of 0.1 to 120 hours.
- compound (A2) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M3) is known or can be produced according to known methods.
- the compound represented by formula (A3) (hereinafter referred to as compound (A3)) is a compound represented by formula (B3) (hereinafter referred to as compound (B3)) and the compound represented by formula (M4) (hereinafter referred to as It can be produced by reacting a compound (M4)) or a salt thereof.
- Salts of compound (M4) include, for example, hydrochloride and sulfate.
- the reaction is usually carried out in a solvent. Solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; Mixtures of the above are included.
- a base may be added to the reaction, if necessary.
- Bases used in the reaction include, for example, organic bases; alkali metal carbonates; alkali metal hydrogencarbonates; sodium hydride and tripotassium phosphate.
- the base is generally used in a proportion of 1 to 10 mol per 1 mol of compound (B3).
- compound (M4) is generally used in a proportion of 1 to 10 mol per 1 mol of compound (B3).
- the reaction temperature is usually within the range of 0-150°C.
- the reaction time is usually within the range of 0.1 to 120 hours.
- the compound (A3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (A3) can also be produced according to the method described in International Publication No. 98/043949 and the like.
- Compound (M4) is known or can be produced according to known methods.
- Compound (A3) is prepared by reacting a compound represented by formula (B4) (hereinafter referred to as compound (B4)) and a compound represented by formula (M5) (hereinafter referred to as compound (M5)) in the presence of a base. It can be produced by reacting.
- a compound represented by formula (B4) hereinafter referred to as compound (B4)
- a compound represented by formula (M5) hereinafter referred to as compound (M5)
- the reaction is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
- Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogencarbonates, sodium hydride and tripotassium phosphate.
- the compound (M5) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B4).
- the reaction temperature is usually within the range of -20 to 150°C.
- the reaction time is usually within the range of 0.1 to 48 hours.
- the compound (A3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M5) is known or can be produced according to known methods.
- Manufacturing method F The compound represented by formula (A4) (hereinafter referred to as compound (A4)) is obtained by reacting compound (B1) and the compound represented by formula (M6) (hereinafter referred to as compound (M6)) with a metal catalyst and a base. It can be produced by reacting in the presence.
- Z 1 represents a nitrogen atom or CR 51
- Z 2 represents a nitrogen atom or CR 52
- Z 3 represents a nitrogen atom or CR 53
- Z 4 represents a nitrogen atom or CR 54 (with the proviso that Z 1 , Z 2 , Z 3 and Z 4 are all nitrogen atoms)
- R 51 , R 52 , R 53 and R 54 are the same or different and one or more substituents selected from group E
- a C3-C6 cycloalkyl group optionally substituted with a group, a C1-C6 chain hydrocarbon group, a C1-C3 alkylthio group ⁇ the C1-C6 chain hydrocarbon group and the C1-C3 alkylthio group are group G optionally substituted with one or more substituents selected from]
- a phenyl group, a 5-6 membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6 membered aromatic heterocyclic group are selected from Group F , OR 13
- the reaction is usually carried out in a solvent.
- Solvents used in the reaction include, for example, ethers, hydrocarbons, amides, water and mixtures of two or more thereof.
- Metal catalysts used in the reaction include copper (I) iodide, copper (I) bromide, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile) copper catalysts such as copper (I) hexafluorophosphate and copper (I) 2-thiophenecarboxylate; and nickel catalysts such as bis(cyclooctadiene) nickel (0) and nickel (II) chloride.
- bases include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium fluoride and tripotassium phosphate.
- a ligand and/or an alkali metal halide may be used for the reaction, if desired.
- ligands include triphenylphosphine, xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphos Phino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2 -aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine,
- the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B1).
- Alkali metal halides include potassium fluoride, sodium fluoride, lithium chloride, sodium chloride and the like.
- the alkali metal halide is usually used in a proportion of 0.1 to 5 mol per 1 mol of compound (B1).
- the compound (M6) is usually used at a ratio of 1 to 10 mol
- the metal catalyst is usually used at a ratio of 0.01 to 2 mol
- the base is usually used at a ratio of 1 to 10 mol, relative to 1 mol of the compound (B1). Used.
- reaction temperature is usually in the range of -20°C to 200°C.
- reaction time is usually in the range of 0.1 to 48 hours.
- compound (A4) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M6) is known or can be produced according to known methods.
- the compound represented by formula (A5) (hereinafter referred to as compound (A5)) is a compound represented by formula (B5) (hereinafter referred to as compound (B5)) and the compound represented by formula (M7) (hereinafter referred to as compound (M7)) in the presence of phosphines and azodiesters.
- the symbols have the same meanings as described above.
- the reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; Phosphines include, for example, triphenylphosphine and trimethylphosphine.
- Azodiesters include, for example, diethyl azodicarboxylate, diisopropyl azodicarboxylate and bis(2-methoxyethyl) azodicarboxylate.
- the compound (M7) is usually used at a ratio of 1 to 10 mol
- the phosphine is usually used at a ratio of 1 to 10 mol
- the azodiester is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the compound (B5).
- the reaction temperature is usually within the range of 0-150°C.
- the reaction time is usually within the range of 0.1 to 48 hours.
- compound (A5) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M7) is known or can be produced according to known methods.
- Manufacturing method H Compound (A5) can also be produced by reacting compound (B5) with a compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a base.
- a compound represented by formula (M8) hereinafter referred to as compound (M8)
- the reaction is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
- Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
- the compound (M8) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B5).
- the reaction temperature is usually within the range of -20 to 150°C.
- the reaction time is usually within the range of 0.1 to 48 hours.
- compound (A5) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M8) is known or can be produced according to known methods.
- the compound represented by formula (A6) (hereinafter referred to as compound (A6)) is a compound represented by formula (B6) (hereinafter referred to as compound (B6)) and the compound represented by formula (M9) (hereinafter referred to as A step of reacting a compound represented by formula (B7) (hereinafter referred to as compound (B7)) with a compound (M9) in the presence of a base (hereinafter referred to as step (I-1)) , and a step of reacting compound (B7) with a compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base (hereinafter referred to as step (I-2)).
- step (I-2) a step of reacting compound (B7) with a compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base (hereinafter referred to as step (I-2)).
- R 55 represents a C1-C4 alkyl group
- X 2 represents an iodine atom, a methoxysulfonyloxy group, a mesyloxy group, or a tosyloxy group, and other symbols have the same meanings as above.
- Step (I-1) is usually carried out in a solvent.
- Solvents used in the reaction include, for example, ethers, amides, and mixtures of two or more thereof.
- Bases used in the reaction include, for example, sodium hydride.
- the compound (M9) is generally used in an amount of 1 mol to 10 mol, and the base is generally used in an amount of 0.5 mol to 5 mol, per 1 mol of the compound (B6).
- the reaction time is usually within the range of 5 minutes to 72 hours.
- the reaction temperature is usually in the range of -20°C to 100°C.
- compound (B7) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M9) is a commercially available compound, or can be produced according to a known method.
- Step (I-2) is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
- Bases used in the reaction include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, and sodium hydride.
- the compound (M10) is generally used in an amount of 1 to 10 mol
- the base is generally used in an amount of 1 to 20 mol, per 1 mol of the compound (B7).
- the reaction temperature is usually in the range of -20 to 100°C.
- the reaction time is usually within the range of 0.1 to 48 hours.
- compound (A6) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M10) is a commercially available compound, or can be produced according to a known method.
- the compound represented by formula (A7) (hereinafter referred to as compound (A7)) is a compound represented by formula (B26) (hereinafter referred to as compound (B26)) and the compound represented by formula (M12) (hereinafter referred to as a compound (M12)) in the presence of a base to obtain a compound represented by formula (B9) (hereinafter referred to as compound (B9)) (hereinafter referred to as step (K-1)) , and a step of reacting compound (B9) with compound (M10) in the presence of a base (hereinafter referred to as step (K-2)).
- R 56 represents a tert-butyl group or an isopentyl group, and other symbols have the same meanings as above. ]
- Step (K-1) is usually carried out in a solvent.
- Solvents used in the reaction include, for example, ethers, amides, alcohols, and mixtures of two or more thereof.
- Bases used in the reaction include, for example, sodium hydride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide (hereinafter referred to as alkali metal alkoxides).
- the compound (M12) is generally used in an amount of 1 mol to 10 mol
- the base is generally used in an amount of 1 mol to 5 mol, per 1 mol of the compound (B6).
- the reaction time is usually within the range of 5 minutes to 72 hours.
- reaction temperature is usually in the range of -20°C to 100°C.
- compound (B9) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M12) is a commercially available compound, or can be produced according to a known method.
- Step (K-2) can be carried out according to step (I-2) of production method I, using compound (B9) instead of compound (B7).
- the compound represented by formula (A8) (hereinafter referred to as compound (A8)) is a compound represented by formula (B10) (hereinafter referred to as compound (B10)) and the compound represented by formula (M13) (hereinafter referred to as compound (M13)) in the presence of a catalyst and a base.
- compound (B10) a compound represented by formula (B10)
- M13 the compound represented by formula (M13)
- the reaction can be carried out according to Production Method A using compound (M13) instead of compound (B1) and compound (B10) instead of compound (M1).
- Compound (M13) is a known compound, or can be produced according to a known method.
- N-oxide of the compound of formula (I) can be prepared by reacting the compound of formula (I) with an oxidizing agent.
- the reaction can be carried out, for example, according to the method described in US Patent Application Publication No. 2018/0009778 or International Publication No. 2016/121970.
- Reference manufacturing method 1 Compound (B7) is prepared by reacting compound (B6) with a compound represented by formula (M11) (hereinafter referred to as compound (M11)) to obtain a compound represented by formula (B8) (hereinafter referred to as compound (B8) and (hereinafter referred to as step (1-1)), and a step of reacting compound (B8) in the presence of an acid to obtain compound (B7) (hereinafter referred to as step (1-2)).
- M11 compound represented by formula (M11)
- step (1-1) a step of reacting compound (B8) in the presence of an acid to obtain compound (B7)
- step (1-2) can be manufactured by [In the formula, symbols have the same meanings as described above. ]
- Step (1-1) is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons, halogenated hydrocarbons, ethers, amides and mixtures of two or more thereof.
- compound (M11) is generally used in a proportion of 1 mol to 10 mol per 1 mol of compound (B6).
- the reaction time is usually within the range of 5 minutes to 72 hours.
- the reaction temperature is usually within the range of -20°C to 200°C.
- compound (B8) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M11) is a commercially available compound, or can be produced according to a known method.
- Step (1-2) is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more thereof.
- Acids used in the reaction include, for example, hydrochloric acid and acetic acid.
- the reaction temperature is usually within the range of -20 to 100°C.
- the reaction time is usually within the range of 0.1 to 48 hours.
- compound (B7) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- the compound represented by formula (B16) (hereinafter referred to as compound (B16)) is a compound represented by formula (B11) (hereinafter referred to as compound (B11)) and the compound represented by formula (M14) (hereinafter referred to as a compound (M14)) in the presence of a catalyst and a base to obtain a compound represented by formula (B12) (hereinafter referred to as compound (B12)) (hereinafter referred to as step (2-1) and a step of reacting compound (B12) in the presence of a base to obtain a compound represented by formula (B13) (hereinafter referred to as compound (B13)) (hereinafter referred to as step (2-2)); A step of reacting compound (B13) with compound (M11) to obtain a compound represented by formula (B14) (hereinafter referred to as compound (B14)) (hereinafter referred to as step (2-3)), compound ( B14) in the presence of an acid to obtain a
- Step (2-1) is usually carried out in a solvent.
- Solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water and mixtures of two or more thereof.
- catalysts used in the reaction include palladium catalysts such as palladium (II) acetate, Pd 2 (dba) 3 , Pd(PPh 3 ) 4 and PdCl 2 (dppf); Copper (I) chloride, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate (I) benzene complex, tetrakis (acetonitrile) copper (I) hexafluorophosphate, copper (I) 2-thiophenecarboxylate ) and other copper catalysts.
- palladium catalysts such as palladium (II) acetate, Pd 2 (dba) 3 , Pd(PPh 3 ) 4 and P
- Bases used in the reaction include, for example, organic bases; alkali metal carbonates; alkali metal hydrogen carbonates; alkali metal phosphates such as tripotassium phosphate (hereinafter referred to as alkali metal phosphates); Acetates such as sodium (hereinafter referred to as acetates) can be mentioned.
- a ligand may be used in the reaction, if necessary.
- Ligands used in the reaction include triphenylphosphine, xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2- Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl, tri-tert-butylphosphine, 1,2-bis(diphenylphosphino)ethane, pyridine-2-carboxylic acid, (L)-proline, trans-1,2-cyclohexane diamine, trans-N,N'-dimethylcyclohexane-1,2-di
- the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B11).
- the compound (M14) is usually used at a ratio of 0.1 to 10 mol
- the catalyst is usually used at a ratio of 0.01 to 1 mol
- the base is usually used at a ratio of 1 to 10 mol, relative to 1 mol of the compound (B11).
- used in The reaction time is usually in the range of 5 minutes to 72 hours.
- the reaction temperature is usually in the range of -20°C to 200°C.
- the compound (B12) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (M14) is a known compound, or can be produced according to a known method.
- Step (2-2) is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more thereof.
- Bases used in the reaction include, for example, alkali metal phosphates and alkali metal alkoxides. In the reaction, a base is generally used in a proportion of 1 to 20 mol per 1 mol of compound (B12).
- Step (2-3) can be carried out according to step (1-1) of Reference Production Method 1, using compound (B13) instead of compound (B6).
- Step (2-4) can be carried out according to step (1-2) of Reference Production Method 1, using compound (B14) instead of compound (B8).
- Step (2-5) can be carried out according to step (I-2) of production method I, using compound (B15) instead of compound (B7).
- the compound represented by formula (B18) (hereinafter referred to as compound (B18)) is obtained by reacting the compound represented by formula (B27) (hereinafter referred to as compound (B27)) and compound (M12) in the presence of a base.
- a step of reacting to obtain a compound represented by formula (B17) (hereinafter referred to as compound (B17)) (hereinafter referred to as step (3-1)), and compound (B17) and compound (M10) with a base It can be produced by a step of reacting in the presence of (hereinafter referred to as step (3-2)).
- step (3-2) the symbols have the same meanings as described above. ]
- the step (3-1) can be carried out according to the step (K-1) of the manufacturing method K, using the compound (B27) instead of the compound (B26).
- the step (3-2) can be carried out according to the step (K-2) of the manufacturing method K, using the compound (B17) instead of the compound (B9).
- Reference manufacturing method 4 Compound (B2) can be produced by reacting compound (B1) with diboronic acid or diboronic acid ester in the presence of a base and a palladium catalyst.
- the reaction is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; Nitriles and mixtures of two or more thereof are included.
- bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, acetates, and tripotassium phosphate.
- Palladium catalysts include, for example, PdCl 2 (dppf).
- Diboronic acids or diboronic acid esters include bis(pinacolato)diboron, tetrahydroxydiborane, and the like.
- the ratio of diboronic acid or diboronic ester is usually 1 to 5 mol
- the ratio of base is usually 1 to 5 mol
- the palladium catalyst is usually 0.01 to 0.5. Used in molar proportions.
- the reaction temperature is generally within the range of 0 to 150° C.
- the reaction time is generally within the range of 0.1 to 48 hours.
- the compound (B2) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Reference manufacturing method 5 Compound (B5) can be produced by oxidizing compound (B2).
- the reaction is usually carried out in a solvent.
- Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more thereof.
- the oxidizing agent used for the reaction include meta-chloroperbenzoic acid and hydrogen peroxide solution.
- a base may be added as necessary. Bases include sodium hydroxide and potassium hydroxide.
- the oxidizing agent is generally used in a proportion of 1 to 5 mol per 1 mol of compound (B2).
- the base is usually used in a proportion of 0.1 to 5 mol per 1 mol of compound (B2).
- the reaction temperature is generally in the range of -20 to 120°C, and the reaction time is generally in the range of 0.1 to 48 hours.
- water and a reducing agent such as sodium thiosulfate are added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are performed to isolate compound (B5). can do.
- the compound (B5) is obtained by reacting a compound represented by the formula (B19) (hereinafter referred to as compound (B19)) with a diboronic acid or a diboronic acid ester in the presence of a base and a palladium catalyst to obtain a compound represented by the formula (B20).
- a step of obtaining a compound (hereinafter referred to as compound (B20)) (hereinafter referred to as step (6-1)), and compound (B20) and compound (M13) are reacted in the presence of a base and a metal catalyst. It can be produced by a process (hereinafter referred to as process (6-2)).
- process (6-2) In the formula, the symbols have the same meanings as described above. ]
- Step (6-1) can be carried out according to Reference Production Method 4 using compound (B19) instead of compound (B1).
- Compound (B19) is a known compound, or can be produced according to a known method.
- Step (6-2) can be carried out according to production method A using compound (B20) instead of compound (M1) and compound (M13) instead of compound (B1).
- the compound represented by formula (B21) (hereinafter referred to as compound (B21)) can be produced by reacting compound (B5) with trifluoroacetic anhydride in the presence of a base.
- a solvent Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
- bases include organic bases.
- trifluoroacetic anhydride is generally used in an amount of 1 to 10 mol
- the base is generally used in an amount of 1 to 10 mol, per 1 mol of compound (B5).
- the reaction temperature is usually within the range of -20 to 100°C.
- the reaction time is usually within the range of 0.1 to 48 hours.
- the compound represented by formula (B22) can be produced by reacting compound (B1) with a compound represented by formula (M15) (hereinafter referred to as compound (M15)).
- compound (M15) a compound represented by formula (M15)
- R 57 represents a methyl group or an ethyl group, and other symbols have the same meanings as above.
- the reaction can be carried out, for example, according to the method described in WO2016/123253.
- Compound (M15) is a commercially available compound, or can be produced according to a known method.
- Reference manufacturing method 9 Compound (B4) can be produced by reacting compound (B3) with hydroxylamine or a salt thereof.
- Salts of hydroxylamine include, for example, hydrochlorides and sulfates. The reaction can be carried out according to production method D using hydroxylamine or a salt thereof instead of compound (M4).
- Reference manufacturing method 10 A compound represented by formula (B23) can be produced by reacting compound (B1) with N-formylsaccharin in the presence of a palladium catalyst, a ligand, triethylsilane and a base. [In the formula, symbols have the same meanings as described above. ] The reaction is described in Angew. Chem. Int. Ed. , 2013, 52, 8611-8615 and the like.
- Reference manufacturing method 11 A compound represented by formula (B24) can be produced by reacting compound (B27) with compound (M1) in the presence of a palladium catalyst and a base. [In the formula, symbols have the same meanings as described above. ]
- reaction can be carried out according to production method A using compound (B27) instead of compound (B1).
- Reference manufacturing method 12 A compound represented by formula (B25) can be produced by reacting compound (B27) with compound (M3) in the presence of a metal catalyst and a base. [In the formula, the symbols have the same meanings as described above. ]
- reaction can be carried out according to production method C using compound (B27) instead of compound (B1).
- the compound of the present invention can be mixed or used in combination with one or more components (hereinafter referred to as the present component) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below. can be done.
- the mixed use or combined use means using the compound of the present invention and this component at the same time, separately or with a time interval.
- the compound of the present invention and the component of the present invention may be contained in separate formulations or may be contained in one formulation.
- composition A One aspect of the present invention is one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (that is, the present component), and the compound of the present invention It is a composition containing (hereinafter referred to as composition A).
- Group (a) includes acetylcholinesterase inhibitors (e.g. carbamate insecticides, organophosphorus insecticides), GABAergic chloride ion channel blockers (e.g. phenylpyrazole insecticides), sodium channel modulators (e.g. pyrethroid insecticides).
- acetylcholinesterase inhibitors e.g. carbamate insecticides, organophosphorus insecticides
- GABAergic chloride ion channel blockers e.g. phenylpyrazole insecticides
- sodium channel modulators e.g. pyrethroid insecticides.
- nicotinic acetylcholine receptor competitive modulators e.g., neonicotinoid insecticides
- nicotinic acetylcholine receptor allosteric modulators glutamatergic chloride channel allosteric modulators (e.g., macrolide insecticides)
- nereistoxin insecticides chitin synthesis inhibitors, moulting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III and IV, voltage dependent from sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal modulators, microbial insecticides, and other insecticidal, acaricidal and nematicidal active ingredients. It is a group of They are described in the IRAC mechanism-based classification.
- Group (b) includes nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeletal inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides).
- nucleic acid synthesis inhibitors e.g., phenylamide fungicides, acyl amino acid fungicides
- cell division and cytoskeletal inhibitors e.g., MBC fungicides
- respiratory inhibitors e.g., QoI fungicides
- QiI fungicides amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine-based fungicides), signal transduction inhibitors, lipid and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMIs such as triazoles) fungicides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides, and other fungicidal active ingredients. They are described in the FRAC mechanism-based classification.
- Group (c) is a group of plant growth-regulating components (including mycorrhizal fungi and rhizobia).
- Group (d) is a group of repellent ingredients.
- alanycarb + SX means the combination of alanycarb and SX.
- the abbreviation SX means any one compound of the present invention selected from the group of compounds SX1 to SX259 described in Examples.
- all of the components described below are known components and can be obtained from commercially available formulations or produced by known methods. If this component is a microorganism, it can also be obtained from a bacteria depository.
- the numbers in parentheses represent CAS RN (registered trademark).
- a combination of this component of group (a) above and a compound of the present invention abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acynonapyr + SX, aphidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha endosulfan -endosulfan + SX, aluminum phosphide + SX, amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos- methyl) + SX, azocyclotin + SX, bark of Celastrus angulatus + SX, bendi
- Kurstaki strain HD-1 + SX Bacillus Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + 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 thuringien sis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var.
- 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 QST71
- the ratio of the compound of the present invention to the component is not particularly limited, but the weight ratio (compound of the present invention:the component) is 1000:1 to 1:1000, 500:1 to 1:500, 100:1. ⁇ 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. .
- the compound of the present invention has efficacy against pests.
- pests include phytopathogenic microorganisms, harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks.
- the compound of the present invention can control plant diseases caused by phytopathogenic microorganisms such as fungi, Oomycete, Phytomyxea, and bacteria.
- Fungi include, for example, Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota and Olpidiomycota. Specifically, the following are mentioned, for example. Parentheses indicate the scientific name of the phytopathogenic microorganism that causes each disease.
- Rice diseases Pyricularia oryzae, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi, Sclerophthora macrospora, Sclerophthora macrospora, and Epicoccum nigrum, Trichoderma viride, Rhizopus oryzae, pseudocolonial blight (Waitea circinata, Ceratobasidium setariae, Thanatephorus cucumeris)); 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 rot (Microdochium nivale, Microdochium majus), snow rot (Typhula
- Polymyxa betae and Polymyxa graminis Diseases caused by bacteria: Burkholderia plantarii of rice, Pantoea ananatis of rice, Xanthomonas oryzae pv. oryzae. of rice, bacterial spot of cucumber (Pseudomonas syringae pv.
- harmful arthropods examples include the following.
- Hemiptera Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus, etc.
- Delphacidae Leafhopper (Nephotettix cincticeps), Leafhopper (Nephotettix virescens), Leafhopper (Nephotettix nigropictus), Leafhopper (Recilia dorsalis), Leafhopper (Empoasca onukii), Potato Leafhopper (Empoasca fabae) , Corn leaf hopper (Dalbulus maidis), White leafhopper (Cofana spectra), Amrasca biguttula biguttula, etc. Cicadellidae; European Spittle Bug (Philaenus spumarius), etc.
- Aphis fabae Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Green peach aphid ( Myzus persicae), Brachycaudus helichrysi, Brevicoryne brassicae, rosy apple aphid (Dysaphis plantaginea), Lipaphis erysimi, Macrosiphum euphorbiae, potato aphid Aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat neck aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach aphid (Hyalopterus pruni), hienoaphis (Melanaphis) sacchari), Tetraneura nigriabdominal
- Aphididae such as Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, and Phylloxera russelae; Adelges tsugae, balsam woolly Adelgidae such as Aphid (Adelges piceae), Aphrastasia pectinatae; stink bug (Eysarcoris aeneus), stink bug (Eysarcoris lewisi), stink bug (Eysarcoris ventralis), stink bug (Eysarcoris annamita), brown stink bug (Halyomorpha halys), green stink bug (Nezara viridula), brown stink bug ( Euschistus heros), red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus, etc.; Pentatomidae; Scaptocoris castanea
- Lepidoptera Chilo suppressalis, Chilo polychrysus, White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Rice hare moth (Marasmia exigua), cotton moth (Notarcha derogata), corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), high spotted moth (Hellula undalis), monkey crocodile moth (Herpetogramma luctuosale), Shibatutoga (Parapediasia teterrellus) , Rice case worm (Nymphula depunctalis), Sugar cane borer (Diatraea saccharalis), Egg plant fruit borer (Leucinodes orbonalis), etc.; Pyralidae such as Euzophera
- Heliothis virescens such as Heliothis virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Velvet bean caterpillar (Anticarsia gemmatalis), Cotton leaf worm (Alabama argillacea), Hop wine borer (Hydraecia immanis) and other noctuids (Noctuidae); Pieridae such as Pieris rapae; orana fasciata), Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Epinotia aporema Tortricidae, such as , Citripestis sagittiferella, European grape wine moss (Lobesia botrana); Gracilariidae such as Caloptilia theivora and Phyllonorycter ringoniella;
- Plutellidae such as Plutella xylostella
- Gelechiidae such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Tuta absolutea
- Arctiidae such as (Hyphantria cunea); Castniidae, such as giant sugar cane borer (Telchin licus); Cossidae, such as Cossus insularis
- Geometridae such as Ascotis selenaria Geometridae
- Limacodidae such as Parasa lepida
- Stathmopodidae such as Stathmopoda Stammssa
- Hesperiidae such as Parnara gut
- Thysanoptera Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips , Echinothrips americanus, Scirtothrips perseae, etc.; Phlaeothripidae, such as Haplothrips aculeatus.
- Anthomyiidae such as Delia platura, Delia antiqua, and Pegomya cunicularia
- Ulidiidae such as Tetanops myopaeformis Agromyzidae, such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola
- Chloropidae such as Chlorops oryzae
- Bactrocera cucurbitae Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, Rjapachla fruit fly ), etc.
- Drosophilidae such as Drosophila melanogaster
- Phoridae such as Megaselia spiracularis
- Psychodidae such as Clogmia albipunctata
- Culicidae such as Prosimulium yezoensis and Simulium ornatum
- Tabanidae such as Tabanus trigonus
- Musca domestica and Muscinasta bulans marbling Muscidae such as Stomoxys calcitrans and Haematobia irritans
- Calliphoridae Sarcophagidae
- Chironomus plumosus Chironomus yoshimatsui
- Glyptotendipes tokunagai of Chironomidae Chironomidae
- Diabrotica spp. e.g. Western Corn Rootworm (Diabrotica virgifera virgifera), Southern Corn Rootworm (Diabrotica undecimpunctata howardi), Northern Corn Rootworm (Diabrotica barberi), Mexican Corn Rootworm (Diabrotica virgifera zeae)), banded cucumber beetle (Diabrotica balteata), cucumber beetle (Diabrotica speciosa) and other bean leaf beetles (Cerotoma trifurcata), neck beetle (Oulema melanopus), cucumber beetle (Aulacophora femoralis), cucumber beetle (Phyllotreta striolata), cabbage-free beetle (Phyllotreta cruciferae), western black-free beetle (Phyllotreta pusilla), cabbage stem-free beetle (Psylliodes chrysocephala), hop-free bee
- Tenebrionidae such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus; Coccinellidae, such as Epilachna vigintioctopunctata; Lyctus brunneus, Rhizopertha dominica, etc.; Ptinidae; Ptinidae; Anoplophora malasiaca, Migdolus fryanus, Aromia bungii, etc.; Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius Limonius spp., Aeolus spp., Elateridae; Paederus fuscipes, Staphylinidae; Anthrenus verbasci, Dermestes maculates ), Trogoderma granarium, etc.
- Hymenoptera Tenthredinidae, such as Athalia rosae and Athalia japonica; Solenopsis spp., such as Solenopsis invicta and Solenopsis geminata, brown leaf-cutting ants (Atta capiguara), Acromyrmex spp., Paraponera clavata, Ochetellus glaver, Monomorium pharaonis, Linepithema humile , Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, etc., Camponotus spp.
- Pogonomyrmex spp. such as Pogonomyrmex occidentalis, Wasmania spp. such as Wasmania auropunctata, Formicidae such as Anoplolepis gracilipes; Vespa mandarinia ), Vespa simillima, Vespa analis, Vespa velutina, Polistes jokahamae, etc.; Siricidae, such as Urocerus gigas ; Bethylidae.
- Blattodea Ectobiidae, such as Blattella germanica; Blatta orientalis); Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticutermes miyatakei), Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.
- Siphonaptera Pulicidae, such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, and Echidnophaga gallinacea; Hectopsyllidae, such as penetrans; Ceratophyllidae, such as the European rat flea (Nosopsyllus fasciatus).
- Pulicidae such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, and Echidnophaga gallinacea
- Hectopsyllidae such as penetrans
- Ceratophyllidae such as the European rat flea (Nosopsyllus fasciatus).
- Psocodae Pediculidae, such as head lice (Pediculus humanus capitis); Pthiridae, such as pubic lice (Pthirus pubis); Haematopinidae); Linognathidae, such as Linognathus vituli, Linognathus ovillus, Solenopotes capillatus; Bovicola bovis, Bovicola forvis, Bovicola breviceps, Damalin Bovicoliidae, such as Werneckiella spp.; Trichodectidae, such as Trichodectes canis and Felicola subrostratus; Menopon gallinae, Menacanthus stramineus ), Menoponidae such as Trinoton spp.; Trimenoponidae such as Cummingsia spp.; Trogiidae such as Trogium pulsatorium; Liposcelidae or Liposcelidida
- Thysanura Lepismatidae, such as Ctenolepisma villosa and Lepisma saccharina.
- Araneae Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii.
- Polydesmida Paradoxosomatidae, such as Oxidus gracilis and Nedyopus tambanus.
- Isopoda Armadillidiidae, such as Armadillidium vulgare.
- Chilopoda Scutigeridae, such as Thereuonema hilgendorfi; Scolopendridae, such as Scolopendra subspinipes; Ethopolyidae, such as Bothropolys rugosus.
- Gastropoda Limacidae, such as Limax marginatus and Limax flavus; Philomycidae, such as Meghimatium bilineatum; Pomacea canaliculata, etc. Lymnaeidae, such as Austropeplea ollula.
- Nematoda Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchidae; Meloidogyne javanica, Meloidogyne incognita, guava root-knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, Heterodera glycines, potato cyst nematode ( Heteroderidae such as Globodera rostochiensis and Globodera pallida; Hoplolimidae such as Rotylenchus reniformis; Anguinidae); Tylenchulidae, such as citrus nematode (Tylenchulus semipenetrans); Longidoridae, such as Xiphinema index; Trichodoridae; Aphelenx family (Parasitaphelenchidae).
- Harmful insects, harmful arthropods such as harmful mites, harmful molluscs and harmful nematodes have reduced drug sensitivity or drug resistance to insecticides, acaricides, molluscicides and nematicides. It may be developed harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes.
- an effective amount of the compound of the present invention or composition A is applied directly to pests and/or to habitats of pests (plants, soil, indoors, animals, etc.). It is done by Examples of the pest control method of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoking treatment, water surface treatment and seed treatment.
- the compound or composition A of the present invention is usually prepared by mixing an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier with a surfactant or the like, and optionally adding a binder, a dispersant, a stabilizer, or the like for formulation.
- solid carriers examples include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice stone, silica sand, chemical fertilizers. fine powders and granules of (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.) and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).
- clay pyrophyllite clay, kaolin clay, etc.
- talc calcium carbonate
- diatomaceous earth zeolite
- bentonite acid clay
- attapulgite white carbon
- ammonium sulfate vermiculite
- perlite perlite
- pumice stone pumice
- liquid carriers examples include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methyl naphthalene, 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 (dimethylsulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic
- gaseous carriers examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.
- surfactants examples include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkylsulfonates, alkylarylsulfonates , alkyl sulfates, etc.).
- formulation adjuvants include binders, dispersants, colorants, stabilizers, etc.
- Specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, Examples include water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, and dibutylhydroxytoluene.
- an adjuvant can be used as a component that enhances or assists the efficacy of the compound of the present invention.
- plants include whole plants, foliage, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs and seedlings.
- the vegetative reproductive organ means the plant's roots, stems, leaves, etc. that have the ability to grow when the part is separated from the main body and placed in the soil.
- Vegetative reproductive organs include, for example, tuberous root, creeping root, bulb, corm or solid bulb, tuber, rhizome, stolon , rhizophore, cane cuttings, propagule and vine cuttings.
- the stolons are sometimes called runners, and the mukago is also called buds, which are divided into broad buds and bulbils.
- a vine means a shoot (collective term for leaves and stems, shoot) of sweet potato, yamanoimo, and the like. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores or tuberous roots are collectively called bulbs. Cultivation of potatoes begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.
- an effective amount of the compound of the present invention or composition A is applied to soil before or after planting plants. and the method of applying. More specifically, for example, planting hole treatment (planting hole spraying, planting hole treatment soil mixing), stock base treatment (stock base spraying, stock base soil mixing, stock irrigation, late seedling period stock base treatment), planting groove Treatment (ditch spraying, ditch soil mixing), cropping treatment (cropping spraying, cropping soil mixing, growing season cropping), cropping treatment at the time of sowing (crop spraying at the time of sowing, cropping soil mixing at the time of sowing) ), full surface treatment (overall soil spraying, full soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spraying treatments (granule spraying during the growing season, foliar spraying, under the canopy or around the trunk) , soil surface spraying, soil surface mixing, sowing hole spraying, furrow ground surface spray
- Seed treatment includes, for example, the treatment of seeds or vegetative reproductive organs with the compound of the present invention or composition A. Specifically, for example, a suspension of the compound of the present invention or composition A is atomized and applied to the seed surface. Alternatively, a spraying treatment in which the surface of the vegetative reproductive organs is sprayed, a smearing treatment in which the compound of the present invention or composition A is applied to seeds or vegetative reproductive organs, and an immersion treatment in which seeds are immersed in a chemical solution of the compound of the present invention or composition A for a certain period of time. , a method of coating seeds or vegetative reproductive organs with a carrier containing the compound of the present invention or composition A (film coating, pellet coating, etc.).
- the vegetative and reproductive organs mentioned above include, in particular, seed potatoes.
- the seed or the vegetative reproductive organ can be treated with the composition A as a single formulation, or the composition A can be divided into a plurality of different formulations and applied to the seeds. Alternatively, it can be processed into vegetative and reproductive organs.
- a method of treating composition A in a plurality of times as different formulations for example, a formulation containing only the compound of the present invention as an active ingredient is treated, seeds or vegetative reproductive organs are air-dried, and then this component is added.
- the seed or vegetative reproductive organ retaining the compound of the present invention or composition A in the present invention means a state in which the compound of the present invention or composition A is attached to the surface of the seed or vegetative reproductive organ. .
- the seed or vegetative reproductive organ holding the compound of the present invention or composition A described above is treated with a compound other than the compound of the present invention or composition A before or after the compound of the present invention or composition A is attached to the seed or vegetative reproductive organ. Materials may be attached.
- the layer when the composition A adheres to the surface of a seed or vegetative reproductive organ in a layer, the layer consists of one layer or multiple layers. Also, when it consists of a plurality of layers, each layer is a layer containing one or more active ingredients, or a layer containing one or more active ingredients and a layer not containing an active ingredient. Become. Seeds or vegetative reproductive organs retaining the compound of the present invention or composition A are obtained, for example, by applying a formulation containing the compound of the present invention or composition A to seeds or vegetative reproductive organs by the method of seed treatment described above. be able to.
- the application rate is generally 1-10000 g of the compound of the present invention per 10000 m 2 .
- the amount of the compound of the present invention is usually applied in the range of 0.001 to 100 g per 1 kg of seeds or vegetative reproductive organs.
- the compound of the present invention or composition A is formulated as an emulsion, wettable powder, flowable powder, etc., it is usually applied after being diluted with water so that the concentration of the active ingredient is 0.01 to 10000 ppm. Agents, powders and the like are usually applied as they are.
- It can also be treated by wrapping a sheet-shaped or string-shaped resin formulation around crops, spreading it around crops, or laying it on the soil at the base of the plant.
- the amount of application is the amount of the compound of the present invention per 1 m 2 of the treated area when the surface is treated.
- the amount is 0.01 to 1000 mg
- the amount of the compound of the present invention per 1 m 3 of space to be treated is usually 0.01 to 500 mg.
- the compound of the present invention or composition A is formulated as an emulsion, wettable powder, flowable preparation, etc., it is usually diluted with water so that the concentration of the active ingredient is 0.1 to 10,000 ppm before application. , aerosol agents, fumigants, poison baits, etc. are applied as they are.
- composition A When the compound of the present invention or composition A is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats, chickens, etc., and small animals such as dogs, cats, rats, mice, etc., veterinary known methods are used. Can be used on animals with As a specific method of use, for the purpose of systemic suppression, for example, it is administered by tablet, feed, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and non-systemic suppression is intended.
- systemic suppression for example, it is administered by tablet, feed, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and non-systemic suppression is intended.
- the amount of the compound of the present invention or composition A when administered to an animal is generally in the range of 0.1-1000 mg per kg body weight of the animal.
- the compound or composition A of the present invention can be used as a pest control agent in agricultural lands such as fields, paddy fields, lawns, and orchards. Examples of plants include the following.
- the plant is not particularly limited as long as it is a variety that is generally cultivated.
- the above plants also include plants that can be produced by natural crossing, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops.
- genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, and EPSP (5 - enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or plants that have been made tolerant to herbicides such as dicamba ; Plants capable of synthesizing selective toxins, etc.
- HPPD 4-hydroxyphenylpyruvate dioxygenase
- ALS acetolactate
- RNAi gene silencing
- Me represents a methyl group
- Et represents an ethyl group
- Pr represents a propyl group
- i-Pr represents an isopropyl group
- Bu represents a butyl group
- i-Bu represents an isobutyl group.
- t-Bu represents a tert-butyl group
- Pen represents a pentyl group
- c-Pr represents a cyclopropyl group
- c-Bu represents a cyclobutyl group
- c-Pen represents a cyclopentyl group
- c-Hex represents a cyclohexyl group
- Ph represents a phenyl group.
- LCMS liquid chromatography/mass spectrometry
- MS mass spectrometry
- Reference production example 2 A mixture of 1.0 g of intermediate 1-5, 1.1 g of bis(pinacolato)diboron, 0.24 g of PdCl 2 (dppf), 0.66 g of tripotassium phosphate, and 30 mL of dimethoxyethane was prepared at 80° C. under a nitrogen atmosphere. Stirred for 6 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 1.0 g of Intermediate 2-1 represented by the following formula.
- Reference production example 3 A mixture of 2.0 g of intermediate 1-5, 0.47 g of bis(triphenylphosphine)palladium(II) dichloride, 4.4 mL of tributyl(1-ethoxyvinyl)tin and 20 mL of 1,4-dioxane was added under a nitrogen atmosphere. at 110° C. for 4 hours. 1N Hydrochloric acid was added to the resulting mixture, and the mixture was stirred at room temperature for 1 hour. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
- Reference Production Example 5-1 The compounds produced according to Reference Production Example 5 and their physical properties are shown below.
- Reference Production Example 7-1 The compounds produced according to Reference Production Example 7 and their physical properties are shown below.
- Production Example 1-1 The compounds produced according to Production Example 1 and their physical properties are shown below.
- Formula (1-1) wherein R 1 , R 2a , R 2b , R 3 , R 4 , X and L are any combination described in [Table A4].
- Invention compound 1-4 1 H-NMR (CDCl 3 ) ⁇ : 7.58 (1H, s), 7.33-7.27 (2H, m), 7.25-7.21 (2H, m), 7.13 (1H, s), 7.09 (1H, s), 7.02-6.98 (1H, m), 3.83 (3H, s), 3.71 (3H, s), 2.43 (3H, s), 2.39 (3H, s), 2.18 (3H, s).
- Invention compound 1-8 1 H-NMR (CDCl 3 ) ⁇ : 8.35 (1H, s), 7.56 (1H, s), 7.43-7.40 (2H, m), 7.38-7.30 (4H, m), 7.05 (1H, s), 5.19 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.36 (3H, s), 2.15 (3H, s).
- Production example 2 0.10 g of intermediate 1-5, 0.02 g of PdCl 2 (PPh 3 ) 2 , 0.15 mL of cyclopropylacetylene, 1.0 mL of tetrabutylammonium fluoride (1 mol/L THF solution) under nitrogen atmosphere, and 3 mL of THF was stirred at 80° C. for 6 hours. Aqueous sodium bicarbonate was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.
- Production example 2-1 The compounds produced according to Production Example 2 and their physical properties are shown below.
- Production example 3 A mixture of 0.18 g of intermediate 4-1, 0.06 mL of butanol, 0.13 g of bis(2-methoxyethyl) azodicarboxylate, 0.13 g of triphenylphosphine, and 4 mL of chloroform was stirred at room temperature for 4 hours. . Aqueous sodium bicarbonate was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
- Production Example 3-1 The compounds produced according to Production Example 3 and their physical properties are shown below.
- Formula (3-1) wherein R 1 , R 2a , R 2b , R 6 , X and L are any combination described in [Table A5].
- Production Example 4-1 The compounds produced according to Production Example 4 and their physical properties are shown below.
- Formula (4-1) wherein R 1 , R 2a , R 2b , R 3a , R 4a , R 5a , R 6a , R 7a , X and L are any combination described in [Table A6].
- Invention compound 4-8 1 H-NMR (CDCl 3 ) ⁇ : 7.35-7.29 (3H, m), 7.23-7.19 (1H, m), 7.17 (1H, s), 6.96 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.26 (3H, s), 2.20 (3H, s).
- Compound 4-9 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.34-7.28 (1H, m), 7.17 (1H, s), 7.00 (1H, s), 6.93-6.86 (3H, m), 4.07 (3H, s), 3.87 (3H, s), 3.82 (3H, s), 2.28 (3H, s), 2.20 (3H, s).
- Invention compound 4-10 1 H-NMR (CDCl 3 ) ⁇ : 7.45-7.39 (1H, m), 7.28-7.25 (1H, m), 7.21-7.17 (3H, m), 6.98 (1H, s) , 4.07 (3H, s), 3.88 (3H, s), 2.27 (3H, s), 2.21 (3H, s).
- Compound 4-11 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.61-7.57 (2H, m), 7.53-7.50 (2H, m), 7.21-7.19 (1H, m), 6.98 (1H, s) , 4.07 (3H, s), 3.88 (3H, s), 2.26 (3H, s), 2.21 (3H, s).
- Compound 4-12 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.41-7.28 (5H, m), 7.16 (1H, s), 6.99 (1H, s), 6.78 (1H, s), 3.97 (3H , s), 2.93 (3H, d), 2.26 (3H, s), 2.20 (3H, s).
- Invention compound 4-13 1 H-NMR (CDCl 3 ) ⁇ : 7.34-7.32 (1H, m), 7.31-7.27 (2H, m), 7.23-7.20 (1H, m), 7.15 (1H, s) , 6.95 (1H, s), 6.79 (1H, br s), 3.98 (3H, s), 2.93 (3H, d), 2.25 (3H, s), 2.19 (3H, s).
- Invention compound 4-15 1 H-NMR (CDCl 3 ) ⁇ : 7.57 (1H, s), 7.31-7.25 (1H , m), 7.17-7.10 (4H, m), 7.00 (1H, s), 3.82 (3H, s), 3.71 (3H, s), 2.38 (3H, s), 2.26 (3H, s), 2.19 ( 3H, s).
- Invention compound 4-18 1 H-NMR (CDCl 3 ) ⁇ : 7.58 (1H, s), 7.37-7.31 (1H, m), 7.16-7.10 (2H, m), 7.08-6.97 (3H, m), 3.84 (3H, s), 3.71 (3H, s), 2.25 (3H, s), 2.20 (3H, s).
- Invention compound 4-25 1 H-NMR (CDCl 3 ) ⁇ : 7.57 (1H, s), 7.47-7.27 (6H, m), 7.13 (1H, s), 7.00 (1H, s), 6.97-6.92 (3H, m), 5.08 (2H, s), 3.82 (3H, s), 3.71 (3H, s), 2.21 (3H, s), 2.19 (3H, s).
- Production example 5 A mixture of 0.18 g of intermediate 2-1,2-bromo-3-fluoropyridine 0.09 mL, PdCl 2 (dppf) 0.02 g, tripotassium phosphate 0.24 g, dimethoxyethane 4 mL and water 1 mL under a nitrogen atmosphere. The mixture was stirred at 80° C. for 8 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
- Production Example 5-1 The compounds produced according to Production Example 5 and their physical properties are shown below.
- Formula (5-1) wherein R 1 , R 2a , R 2b , E b , X and L are any combination described in [Table B2]. ( ⁇ represents the bonding site with the benzene ring.)
- Compound 5-2 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.89 (1H, t), 7.63-7.57 (3H, m), 7.19 (1H, s), 7.17 (1H, s), 3.83 (3H , s), 3.70 (3H, s), 2.40 (3H, s), 2.20 (3H, s).
- Compound 5-3 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.18 (1H, s), 7.13 (1H, d), 7.01 (1H, s), 6.90 (1H, d), 4.07 (3H, s ), 3.87 (3H, s), 2.22 (3H, s), 2.20 (3H, s).
- Compound 5-4 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.18 (1H, s), 7.13 (1H, d), 7.01 (1H, s), 6.90 (1H, d), 4.07 (3H, s ), 3.87 (3H, s), 2.22 (3H, s), 2.20 (3H, s).
- Compound 5-5 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.87 (1H, s), 7.84 (1H, s), 7.58 (1H, s), 7.16 (1H, s), 7.07 (1H, s ), 3.84 (3H, s), 3.72 (3H, s), 2.35 (3H, s), 2.18 (3H, s).
- Production example 6 A mixture of 0.10 g of intermediate 1-5, 0.08 g of 1-cyclopentenylboronic acid, 0.02 g of PdCl 2 (dppf), 0.21 g of tripotassium phosphate, 4 mL of dimethoxyethane and 1 mL of water under nitrogen atmosphere. Stir at 80° C. for 6 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
- Production Example 6-1 The compounds produced according to Production Example 6 and their physical properties are shown below.
- Combination A consists of substituent numbers ZA1 to ZA364.
- Substituent numbers ZA1 to ZA364 represent the combination of R 3 and R 4 in compound (1A), and are hereinafter referred to as [substituent numbers; R 3 , R 4 ].
- Substituent Number ZA2 means a combination in which R3 is an ethyl group and R4 is a hydrogen atom.
- X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is an ethyl group, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX2).
- compound group SX2 is a fluorine atom
- R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX3).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a chlorine atom, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX4).
- compound (1A) is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a methoxy group, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX5).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a cyclopropyl group, and R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX6).
- compound (1A) is CH, L is an oxygen atom, R 1 is a fluorine atom, R X22 is a methyl group, and R 3 and R 4 are any combination described in combination A (hereinafter referred to as compound group SX7).
- X is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a fluorine atom, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX8).
- compound (1A) is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a chlorine atom, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX9).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a methyl group, and R 3 and R 4 are any combination described in Combination A (hereinafter referred to as compound group SX10).
- compound group SX10 is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a fluorine atom, and R 3 and R 4 are any of combination A
- a compound that is a combination hereeinafter referred to as compound group SX11).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, and R 3 and R 4 are any of the combinations described in combination A.
- a compound that is a combination (hereinafter referred to as compound group SX12).
- compound group SX13 A compound that is a combination
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methyl group
- R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX13).
- compound (1A) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is an ethyl group, and R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX14).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a fluorine atom
- R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX15).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a chlorine atom
- R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX16).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methoxy group
- R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX17).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- R 3 and R 4 are any of combination A
- a compound that is a combination of hereinafter referred to as compound group SX18).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a methyl group
- R 3 and R 4 are any of combination A
- a compound that is a combination hereinafter referred to as compound group SX19.
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX20).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX21).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a methyl group
- R 3 and R 4 are any of combination A
- a compound that is a combination hereinafter referred to as compound group SX22).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX23).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R X2 is a chlorine atom
- R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX24).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a methyl group
- R 3 and R 4 are any of combination A A compound that is a combination
- SX25 a compound that is a combination
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is an ethyl group
- R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX26).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R X2 is a fluorine atom
- R 3 and R 4 are any of combination A A compound that is a combination
- SX27 a compound that is a combination
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a chlorine atom
- R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX28).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a methoxy group
- R 3 and R 4 are any of combination A
- a compound that is a combination hereinafter referred to as compound group SX29.
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX30).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R x2 is a methyl group
- any combination of R 3 and R 4 described in combination A hereinafter referred to as compound group SX31.
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- R 3 and R 4 are any of combination A
- a compound that is a combination hereinafter referred to as compound group SX32).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R X2 is a chlorine atom
- R 3 and R 4 are any of combination A
- a compound that is a combination hereinafter referred to as compound group SX33.
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R x2 is a methyl group
- any combination of R 3 and R 4 described in combination A hereinafter referred to as compound group SX34).
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R X2 is a fluorine atom
- R 3 and R 4 are any of combination A A compound that is a combination
- SX35 a compound that is a combination
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R X2 is a chlorine atom
- R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX36).
- Group V Me, Et, Pr, i-Pr, c-Pr, c-Bu, c-Pen, c-Hex, ( CH2 ) 3CH3 , CH2CH ( CH3 ) 2 , CH ( CH3 ) CH2CH3 , t-Bu,CH2c-Pr,( CH2 ) 4CH3 ,( CH2 )2CH ( CH3 ) 2 ,CH ( CH3 ) ( CH2 ) 2CH3 , CH ( CH2CH3 ) CH2CH3 , CH2CH ( CH3 ) CH2CH3 , C ( CH3 ) 2CH2CH3 , CH2t -Bu,CH2c - Bu, CH2c- Pen,( CH2 )2c-Pr,(1-methylcyclopropyl)methyl,( 2 -methylcyclopropyl)methyl,1-cyclopropylethyl,( CH2 ) 3c -Pr, ( CH2 ) 5CH3 ,(
- X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is an ethyl group, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX38).
- compound (1B) X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a fluorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX39).
- X is CH, L is an oxygen atom, R1 is a methyl group, R2 is a chlorine atom, and R5 is any substituent selected from group V.
- compound group SX40 Compound (hereinafter referred to as compound group SX40).
- compound (1B) X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a methoxy group, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX41).
- compound (1B) X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a cyclopropyl group, and R 5 is any substituent selected from group V;
- a certain compound hereinafter referred to as compound group SX42).
- compound (1B) X is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a fluorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX44).
- X is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a chlorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX45).
- compound group SX45 Compound (1B) wherein X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a methyl group, and R 5 is any substituent selected from Group V (hereinafter referred to as compound group SX46).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a fluorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX47).
- compound (1B) X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX48).
- X is a nitrogen atom, L is an oxygen atom, R1 is a methyl group, R2 is a methyl group, and R5 is any substituent selected from group V ;
- a certain compound hereinafter referred to as compound group SX49).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X2 is an ethyl group, and R 5 is any substituent selected from group V;
- a certain compound hereinafter referred to as compound group SX50).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X2 is a fluorine atom, and R 5 is any substituent selected from group V;
- a certain compound hereinafter referred to as compound group SX51).
- X is a nitrogen atom, L is an oxygen atom, R1 is a methyl group, R2 is a chlorine atom, and R5 is any substituent selected from group V ;
- a certain compound hereinafter referred to as compound group SX52).
- X is a nitrogen atom, L is an oxygen atom, R1 is a methyl group, R2 is a methoxy group, and R5 is any substituent selected from group V ;
- a certain compound hereinafter referred to as compound group SX53).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is a cyclopropyl group, and R 5 is any substituent selected from group V (hereinafter referred to as compound group SX54).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a methyl group
- R 5 is any substituent selected from group V.
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- R 5 is any substituent selected from group V
- a certain compound hereinafter referred to as compound group SX56).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R X2 is a chlorine atom
- R 5 is any substituent selected from group V
- SX57 A certain compound (hereinafter referred to as compound group SX57).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a methyl group
- R 5 is any substituent selected from group V.
- compound hereinafter referred to as compound group SX58).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a fluorine atom, and R 5 is any substituent selected from group V; A certain compound (hereinafter referred to as compound group SX59).
- compound (1B) X is a nitrogen atom, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, and R 5 is any substituent selected from group V
- X is a nitrogen atom, L is NH, R1 is a methyl group, R2 is a methyl group, and R5 is any substituent selected from group V.
- compound (1B) X is a nitrogen atom, L is NH, R1 is a methyl group, R2 is an ethyl group, and R5 is any substituent selected from group V.
- compound group SX62 Compound (hereinafter referred to as compound group SX62).
- compound (1B) X is a nitrogen atom, L is NH, R1 is a methyl group, R2 is a fluorine atom, and R5 is any substituent selected from group V.
- X is a nitrogen atom
- L is NH
- R1 is a methyl group
- R2 is a chlorine atom
- R5 is any substituent selected from group V.
- X is a nitrogen atom
- L is NH
- R1 is a methyl group
- R2 is a methoxy group
- R5 is any substituent selected from group V.
- X is a nitrogen atom
- L is NH
- R1 is a methyl group
- R2 is a cyclopropyl group
- R5 is any substituent selected from group V ;
- a certain compound hereinafter referred to as compound group SX66.
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX68).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R X2 is a chlorine atom
- R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX69).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a chlorine atom, and R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX75).
- compound (2B) X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a methoxy group, and R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX76).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x28 is a methyl group, and R 5 is any substituent selected from group V;
- a certain compound hereinafter referred to as compound group SX77).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X28 is a fluorine atom, and R 5 is any substituent selected from group V;
- a certain compound hereinafter referred to as compound group SX78).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x28 is a chlorine atom
- R 5 is any substituent selected from group V A certain compound (hereinafter referred to as compound group SX79).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a methyl group
- R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX80).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a fluorine atom
- R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX81).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a chlorine atom
- R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX82).
- Group Y Et, Pr, i-Pr, ( CH2 ) 3CH3, CH2CH(CH3)2 , CH ( CH3 ) CH2CH3 , C( CH3 ) 3 , CH2c - Pr ,( CH2 ) 4CH3 ,( CH2 )2CH( CH3 ) 2 , CH ( CH3 ) ( CH2 ) 2CH3 ,CH ( CH2CH3 ) CH2CH3 , CH2CH ( CH3 ) CH2CH3 ,C( CH3 ) 2CH2CH3 ,CH2C(CH3)3 , CH2c - Bu , CH2c - Pen, CH2c - Hex,( CH2 ) 2c - Pr,(1-methylcyclopropyl)methyl,(2-methylcyclopropyl)methyl,1-cyclopropylethyl,( CH2 ) 3c -Pr,( CH2 ) 5CH3 ,( CH2 ) 3CH ( CH3 ) 2
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is an ethyl group, and R 6 is any substituent selected from group Y compound (hereinafter referred to as compound group SX84).
- compound group SX84 is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a fluorine atom, and R 6 is any substituent selected from group Y.
- compound SX85 compound (hereinafter referred to as compound group SX85).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a chlorine atom, and R 6 is any substituent selected from group Y.
- compound group SX86 Compound (hereinafter referred to as compound group SX86).
- compound group SX87 Compound (hereinafter referred to as compound group SX87).
- compound (1C) X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a cyclopropyl group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX88).
- X is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a fluorine atom, and R 6 is any substituent selected from group Y compound (hereinafter referred to as compound group SX90).
- compound (1C) is CH, L is an oxygen atom, R 1 is a fluorine atom, R x2 is a chlorine atom, and R 6 is any substituent selected from group Y.
- compound group SX91 Compound (hereinafter referred to as compound group SX91).
- compound group SX92 Compound (1C) wherein X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a methyl group, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX92).
- compound (1C) X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a fluorine atom, and R 6 is any substituent selected from group Y.
- compound group SX93 Compound (hereinafter referred to as compound group SX93).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, and R 6 is any substituent selected from group Y.
- compound group SX94 compound (hereinafter referred to as compound group SX94).
- compound (1C) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is a methyl group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX95).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is an ethyl group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX96).
- compound (1C) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X2 is a fluorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX97).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X2 is a chlorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX98).
- compound (1C) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is a methoxy group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX99).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX100).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a methyl group
- R 6 is any substituent selected from group Y.
- Compound hereinafter referred to as compound group SX101).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a fluorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX102).
- compound (1C) X is a nitrogen atom, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a chlorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX103).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a methyl group
- R 6 is any substituent selected from group Y.
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R X2 is a fluorine atom
- R 6 is any substituent selected from group Y
- a certain compound hereinafter referred to as compound group SX105).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R X2 is a chlorine atom
- R 6 is any substituent selected from group Y
- a certain compound hereinafter referred to as compound group SX106.
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a methyl group
- R 6 is any substituent selected from group Y.
- Compound hereinafter referred to as compound group SX107).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is an ethyl group
- R 6 is any substituent selected from group Y.
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a fluorine atom
- R 6 is any substituent selected from group Y.
- compound group SX109 Compound (hereinafter referred to as compound group SX109).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a chlorine atom
- R 6 is any substituent selected from group Y.
- compound group SX110 Compound (hereinafter referred to as compound group SX110).
- compound group SX111 Compound (hereinafter referred to as compound group SX111).
- compound (1C) X is a nitrogen atom, L is NH, R1 is a methyl group, R2 is a cyclopropyl group, and R6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX112).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- R 6 is any substituent selected from group Y.
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- R 6 is any substituent selected from group Y.
- compound group SX117 Compound (hereinafter referred to as compound group SX117).
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R x2 is a chlorine atom
- R 6 is any substituent selected from group Y.
- compound group SX118 Compound (hereinafter referred to as compound group SX118).
- Formula (2C) In the compound represented by (hereinafter referred to as compound (2C)), X is CH, L is an oxygen atom, R 1 is a methyl group, R is a methyl group, and m is 2 , R X3 , R X4 , R X5 , R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX119).
- Combination B consists of substituent numbers ZB1 to ZB306.
- Substituent numbers ZB1 to ZB306 are compound (2C), compounds represented by formula (1D), and combinations of R x3 , R x4 , R x5 , R x6 , and R x7 in compounds represented by formula (2D) and is hereinafter referred to as [substituent number; R X3 , R X4 , R X5 , R X6 , R X7 ].
- Substituent Number ZB2 means a combination in which R X3 is a methyl group and R X4 , R X5 , R X6 and R X7 are hydrogen atoms.
- X is CH
- L is an oxygen atom
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- m is 2, R X3 , R X4 , R X5 ,
- R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX120).
- X is CH
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- m is 2, R x3 , R x4 , R x5
- R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX121).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a fluorine atom, m is 2, R x3 , R x4 , R x5 , Compounds in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX122).
- compound group SX122 Compounds in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX122).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, m is 2, R X3 , R X4 , R X5 , A compound in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX123).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methyl group
- m is 3, R x3 , R x4 , R x5
- SX124 A compound in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX124).
- X is CH
- L is an oxygen atom
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- m is 3, R X3 , R X4 , R X5
- R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX125).
- X is CH
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- m is 3, R x3 , R x4 , R x5
- R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX126).
- X is CH
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- m is 3, R x3 , R x4 , R x5
- R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX127).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, m is 3, R X3 , R X4 , R X5 , Compounds in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX128).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a methyl group, m is 4, R x3 , R x4 , R x5 , A compound in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX129).
- X is CH
- L is an oxygen atom
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- m is 4, R X3 , R X4 , R X5 ,
- R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX130).
- X is CH
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- m is 4, R x3 , R x4 , R x5
- R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX131).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a fluorine atom, m is 4, R x3 , R x4 , R x5 , Compounds in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX132).
- compound group SX132 Compounds in which R X6 and R X7 are any combination described in combination B
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, m is 4, R X3 , R X4 , R X5 , A compound in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX133).
- Compound hereinafter referred to as compound group SX135).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a chlorine atom, and R 6 is any substituent selected from group Y Compound (hereinafter referred to as compound group SX136).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a methoxy group, and R 6 is any substituent selected from group Y Compound (hereinafter referred to as compound group SX137).
- X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x28 is a methyl group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX138).
- compound (3C) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x28 is a fluorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX139).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x28 is a chlorine atom
- R 6 is any substituent selected from group Y
- SX140 a certain compound
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a methyl group
- R 6 is any substituent selected from group Y
- compound group SX141 Compound
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a fluorine atom
- R 6 is any substituent selected from group Y.
- compound group SX142 Compound (hereinafter referred to as compound group SX142).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a chlorine atom
- R 6 is any substituent selected from group Y.
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is an ethyl group, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX145).
- compound group SX145 is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a fluorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX146).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a chlorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX147).
- compound (1D) is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a methoxy group, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX148).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a cyclopropyl group, and R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX149).
- compound (1D) is CH, L is an oxygen atom, R 1 is a fluorine atom, R x2 is a methyl group, and R x3 , R x4 , R x5 , R x6 and R x7 are combined A compound that is any combination described in B (hereinafter referred to as compound group SX150).
- X is CH, L is an oxygen atom, R 1 is a fluorine atom, R x2 is a fluorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX151).
- X is CH, L is an oxygen atom, R 1 is a fluorine atom, R x2 is a chlorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX152).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a methyl group, and R x3 , R x4 , R x5 , R x6 and R x7 are combined A compound that is any combination described in B (hereinafter referred to as compound group SX153).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a fluorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX154).
- X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a chlorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX155).
- compound (1D) is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is a methyl group, and R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX156).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is an ethyl group
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX157).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a fluorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX158).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a chlorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX159).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methoxy group
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX160).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a methyl group
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX162).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a fluorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX163).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX164).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a methyl group
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX165).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX166).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a chlorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX167).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a methyl group
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX168).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is an ethyl group
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX169).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a fluorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX170).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a chlorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX171).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a methoxy group
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX172).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX173).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R x2 is a methyl group
- R x3 , R x4 , R x5 , R x6 and R x7 are combined A compound that is any combination described in B (hereinafter referred to as compound group SX174).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R x2 is a fluorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX175).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX176).
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R x2 is a methyl group
- R x3 , R x4 , R x5 , R x6 and R x7 are combined A compound that is any combination described in B (hereinafter referred to as compound group SX177).
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX178).
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R x2 is a chlorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX179).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a fluorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX181).
- compound group SX182 is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a chlorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX182).
- X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a methoxy group, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX183).
- compound group SX183 A compound that is any combination described in combination B
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x28 is a methyl group
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX184).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x28 is a fluorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX185).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x28 is a chlorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX186).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a methyl group
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX187).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a fluorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX188).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x28 is a chlorine atom
- R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX189).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R is a methyl group
- the structure of G and G wherein the substituents R x8 , R x9 , R x10 and R x11 corresponding to the structure of are any combination described in combination C (hereinafter referred to as compound group SX190 ).
- Combination C consists of substituent numbers ZC1-ZC1459.
- the substituent numbers ZC1 to ZC1459 represent the structure of G in the compound (1E) and the compound represented by the formula (2E) and the combination of the substituents R x8 , R x9 , R x10 and R x11 corresponding to the structure of G. hereinafter referred to as [substituent numbers; G, R X8 , R X9 , R X10 , R X11 ].
- Substituent Number ZC2 means a combination in which G is G1, R X8 is a methyl group, and R X9 , R X10 and R X11 are hydrogen atoms.
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is an ethyl group
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX191).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX192).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX193).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methoxy group
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX194).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX195).
- X is CH
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a methyl group
- the structure of G and the substituents R x8 and R corresponding to the structure of G Compounds in which X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX196).
- X is CH
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a methyl group
- the structure of G and the substituents R x8 and R corresponding to the structure of G Compounds in which X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX199).
- X is CH
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX200).
- X is CH
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX201).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methyl group
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX202).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is an ethyl group
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX203).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX204).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX205).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methoxy group
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX206).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R is a cyclopropyl group
- the structure of G and the substituent R corresponding to the structure of G Compounds in which X8 , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX207).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a methyl group
- the structure of G and the substituent R x8 corresponding to the structure of G, Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX208).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX209).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX210).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a methyl group
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX211).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX212).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a chlorine atom
- R is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX213).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a methyl group
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX214).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is an ethyl group
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX215).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G, Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX216).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX217).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a methoxy group
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX218).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX219).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R x2 is a methyl group
- the structure of G and the substituents R x8 and R corresponding to the structure of G Compounds in which X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX220).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G
- Compounds in which R X9 , R X10 and R X11 are any combination described in combination C hereinafter referred to as compound group SX221).
- X is a nitrogen atom
- L is NH
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G
- Compounds in which R X9 , R X10 and R X11 are any combination described in combination C hereinafter referred to as compound group SX222).
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R is a methyl group
- the structure of G and the substituents R x8 and R corresponding to the structure of G Compounds in which X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX223).
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G
- Compounds in which R X9 , R X10 and R X11 are any combination described in combination C hereinafter referred to as compound group SX224).
- X is a nitrogen atom
- L is NH
- R 1 is a chlorine atom
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX225).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R is a methyl group
- the structure of G and G wherein the substituents R x8 , R x9 , R x10 and R x11 corresponding to the structure of are any combination described in combination C (hereinafter referred to as compound group SX226 ).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX227).
- X is CH
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methoxy group
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX229).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a methyl group
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX230).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX231).
- X is a nitrogen atom
- L is an oxygen atom
- R 1 is a methyl group
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX232).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a methyl group
- the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX233).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a fluorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G, Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX234).
- X is a nitrogen atom
- L is NH
- R 1 is a methyl group
- R x2 is a chlorine atom
- the structure of G and the substituent R x8 corresponding to the structure of G
- Compounds in which R X9 , R X10 and R X11 are any combination described in combination C hereinafter referred to as compound group SX235).
- R 1 is a methyl group
- R x2 is a methyl group
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 Compounds in which R X18 , R X19 and R X20 are any combination described in combination D (hereinafter referred to as compound group SX236).
- Combination D consists of substituent numbers ZD1 to ZD30.
- Substituent numbers ZD1 to ZD30 represent a combination of R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 in compound (1F).
- the substituent number ZD2 means a combination in which R x12 is a methyl group and R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are hydrogen atoms. .
- R 1 is a methyl group
- R x2 is an ethyl group
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX237).
- R 1 is a methyl group
- R x2 is a fluorine atom
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX238).
- R 1 is a methyl group
- R x2 is a chlorine atom
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX239).
- R 1 is a methyl group
- R x2 is a methoxy group
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX240).
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 is any combination described in combination D (hereinafter referred to as compound group SX241).
- R 1 is a fluorine atom
- R x2 is a methyl group
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are combined
- a compound that is any combination described in D hereinafter referred to as compound group SX242.
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 , R X19 and R X20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX243).
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX244).
- R 1 is a chlorine atom
- R X2 is a methyl group
- R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 , R X19 and R X20 are combined
- a compound that is any combination described in D hereinafter referred to as compound group SX245).
- R 1 is a chlorine atom
- R x2 is a fluorine atom
- R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX246).
- R 1 is a chlorine atom
- R X2 is a chlorine atom
- R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 , R X19 and R X20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX247).
- R 1 is a methyl group
- R x2 is a methyl group
- Combination E consists of substituent numbers ZE1 to ZE20.
- Substituent numbers ZE1 to ZE20 represent a combination of R x21 , R x22 , R x23 , R x24 , R x25 , R x26 and R x27 in compound (2F), and hereinafter, [substituent number; R X21 , R X22 , R X23 , R X24 , R X25 , R X26 , R X27 ].
- the substituent number ZE2 means a combination in which R x21 is a methyl group and R x22 , R x23 , R x24 , R x25 , R x26 and R x27 are hydrogen atoms.
- R 1 is a methyl group
- R x2 is an ethyl group
- R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E
- a compound that is a combination of (hereinafter referred to as compound group SX249).
- R 1 is a methyl group
- R x2 is a fluorine atom
- R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of combination E
- a compound that is a combination of hereinafter referred to as compound group SX250).
- R 1 is a methyl group
- R x2 is a chlorine atom
- R x21 , R x22 , R x23 , R x24 , R x25 , R x26 and R x27 are any of those described in combination E
- compound group SX251 compound that is a combination of
- R 1 is a methyl group
- R x2 is a methoxy group
- R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E
- a compound that is a combination of (hereinafter referred to as compound group SX252).
- R 1 is a methyl group
- R x2 is a cyclopropyl group
- R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are according to combination E Any combination of compounds (hereinafter referred to as compound group SX253).
- R 1 is a fluorine atom
- R x2 is a methyl group
- R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E (hereinafter referred to as compound group SX254).
- R 1 is a fluorine atom
- R X2 is a fluorine atom
- R X21 , R X22 , R X23 , R X24 , R X25 , R X26 , and R X27 are any of those described in combination E
- a compound that is a combination of (hereinafter referred to as compound group SX255).
- R 1 is a fluorine atom
- R x2 is a chlorine atom
- R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E
- a compound that is a combination of (hereinafter referred to as compound group SX256).
- R 1 is a chlorine atom
- R x2 is a methyl group
- R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E (hereinafter referred to as compound group SX257).
- R 1 is a chlorine atom
- R X2 is a fluorine atom
- R X21 , R X22 , R X23 , R X24 , R X25 , R X26 , and R X27 are any of those described in combination E
- a compound that is a combination of (hereinafter referred to as compound group SX258).
- R 1 is a chlorine atom
- R X2 is a chlorine atom
- R X21 , R X22 , R X23 , R X24 , R X25 , R X26 and R X27 are any of those described in combination E
- a compound that is a combination of (hereinafter referred to as compound group SX259).
- Compound S of the present invention represents compounds described in compound groups SX1 to SX259.
- Formulation example 1 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 of the present invention, and 55 parts of water are mixed and finely pulverized by a wet pulverization method. By doing so, a formulation is obtained.
- Formulation example 2 A formulation is obtained by pulverizing and mixing 50 parts of any one compound S of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica.
- Formulation example 3 5 parts of any one of the compounds S of the present invention, 9 parts of polyoxyethylene styryl phenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide additions: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are mixed. By doing so, a formulation is obtained.
- Formulation example 4 2 parts of any one of the compound S of the present invention, 1 part of silica, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, kneaded with an appropriate amount of water, and granulated. After granulating with, the formulation is obtained by drying.
- Formulation example 5 10 parts of any one of the compounds S of the present invention are mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, to which 6.3 parts of GERONOL® TE250, Ethylan® NS-500LQ2 are added. Add .7 parts and 54 parts solvent naphtha and mix to obtain a formulation.
- Formulation example 6 0.1 part of any one of the compound S of the present invention and 39.9 parts of kerosene are mixed and dissolved, placed in an aerosol container, and liquefied petroleum gas (propane, butane and isobutane mixture; saturated vapor pressure: 0.47 MPa (25 C))) to obtain a formulation by filling 60 parts.
- liquefied petroleum gas propane, butane and isobutane mixture; saturated vapor pressure: 0.47 MPa (25 C)
- Formulation example 7 0.2 parts of any one of the compounds S of the present invention, 50 parts of pyrethrum extract lees powder, 30 parts of tab powder and 19.8 parts of wood powder are mixed, kneaded by adding an appropriate amount of water, and extruded into a plate shape.
- the formulation is obtained by sheeting and coiling with a punch.
- Test Examples 1 to 8 is a test section performed under the same conditions as described in each Test Example except that DMSO is dispensed instead of the DMSO diluted solution containing the compound of the present invention. represents Further, "no treatment" in Test Examples 9 to 19 means that the water-diluted formulation containing the compound of the present invention was not sprayed.
- the untreated section in Test Examples 20 and 23 means a section in which the same operation as the treated section is performed except that no test compound is used.
- Test Example 1 Control test against wheat leaf blight fungus (Septoria tritici) Compounds of the present invention 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 2-1, 3-1, 3 -2, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 5-1, 6-1, 1-7, 1-8, 1-9, 2-2 , 2-3, 3-3, 3-4, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4 -16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28 , 4-29, 4-30, 5-2, 5-3, 5-4, 5-5, or 6-2 is diluted with DMSO to contain 150 ppm, and 1 ⁇ L is dispensed to a titer plate (96 wells) After that, 150 ⁇ L of YBG medium previously inoculated with spores of wheat leaf
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was defined as the growth rate of the wheat leaf blight fungus.
- the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
- Test Example 2 Control test against Phytophthora capsici Compounds of the present invention 1-2, 1-7, 1-8, 1-9, 2-3, 4-7, 4-9, 4-13, Dilute 4-14, 4-15, 4-16, 4-18, 4-19, or 4-20 with DMSO to contain 150 ppm, dispense 1 ⁇ L into a titer plate (96 wells), and then add cucumber in advance. 150 ⁇ L of a potato decoction liquid medium (PDB medium) inoculated with spores of Gray-like Phytophthora was dispensed. This plate was cultured at 27° C.
- PDB medium potato decoction liquid medium
- the absorbance at 550 nm of each well of the titer plate was measured to determine the growth rate of Cucurbitaceae Botrytis.
- the growth rate in the section treated with the compound of the present invention was 50% or less of the growth rate in the untreated section.
- Test Example 3 Control test against seedling blight (Pythium ultimum) Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-3, 1 -5, 1-6, 1-7, 1-8, 1-9, 2-3, 3-1, 3-2, 3-4, 4-7, 4-8, 4-9, 4-12 , 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-23, 4-24, 4-25, 4-26, 4 -27, 4-28, 4-29, 5-1, or 5-2 diluted with DMSO to contain 150 ppm, dispensed 1 ⁇ L into a titer plate (96 wells), and then spores of seedling blight in advance 150 ⁇ L of the Czapek medium inoculated with .
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was defined as the growth rate of the damping-off fungus.
- the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
- Test Example 4 Control test against corn smut (Ustilago maydis) Compounds of the present invention 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-5, 1-7, 1- 8, 1-9, 2-3, 4-1, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-19, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-4, or 6 -2 was diluted with DMSO to contain 150 ppm, 1 ⁇ L was dispensed into a titer plate (96 wells), and then 150 ⁇ L of potato decoction liquid medium (PDB medium) previously inoculated with corn smut spores was dispensed.
- PDB medium potato decoction liquid medium
- This plate was cultured at 18° C. for 4 days to grow the corn smut fungus, and then the absorbance at 550 nm of each well of the titer plate was measured to determine the growth rate of the corn smut fungus.
- the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
- Test Example 5 Control test against Rhynchosporium secalis Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1- 3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4- 17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 was diluted with DMSO to contain 150 ppm, and 1 ⁇ L was dispensed into a titer plate (96 wells).
- Test Example 6 Control test against cucumber gray mold (Botrytis cinerea) Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1 -3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4 , 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4 -17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29 , 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 is diluted with DMSO to contain 150 ppm, and 1 ⁇ L is dispensed to a titer plate (96 well) After that, 150 ⁇ L of a complete medium previously inoculated with spores of Botrytis botrytis was
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the cucumber botrytis.
- the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
- Test Example 7 Control test against peach scab (Cladosporium carpophilum) Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1- 3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4- 17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 was diluted with DMSO to contain 150 ppm, and 1 ⁇ L was dispensed into a titer plate (96 wells).
- Test Example 8 Control test against rice sesame leaf blight fungus (Cochliobolus miyabeanus) Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3- 4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-24, 4-25, 4-26, 4-27, 4-29, 4-30, 5- 1, 5-2, 5-3, 5-4, or 5-5 is diluted with DMSO to contain 150 ppm, and 1 ⁇ L is dispensed into a titer plate (96 wells), and then spores of rice sesame leaf blight fungus are added in advance.
- DMSO DMSO
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the rice and sesame leaf blight fungus.
- the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
- Test Example 9 Prevention test against soybean rust (Phakopsora pachyrhizi) A leaf disc having a diameter of 1 cm was cut out from a true leaf of soybean (variety: Kurosengoku). After 1 mL of agar medium (agar concentration: 1.2%) was dispensed into each well of a 24-well microplate, one leaf disk was placed on each well of the agar medium. To a mixture of 0.5 ⁇ L of Sorpol® 1200KX, 4.5 ⁇ L of DMSO and 5 ⁇ L of xylene, 20 ⁇ L of DMSO solution containing 10000 ppm of the test compound was added and mixed.
- the obtained mixture was diluted with ion-exchanged water to prepare a mixture containing the test compound at a predetermined concentration. 10 ⁇ L of the resulting mixture was spread on each leaf disc.
- an aqueous spore suspension (1.0 ⁇ 10 5 /mL) of Phakopsora pachyrhizi having an amino acid substitution of F129L in the mitochondrial cytochrome b protein was spray-inoculated onto the leaf discs. After inoculation, the plants were placed in an artificial climate chamber (6 hours light, 18 hours light off, temperature 23°C, humidity 60%). After one day, the leaf disc was air-dried until no water droplets were left on the surface, and placed again in the climate chamber for 12 days.
- the lesion area of soybean rust was investigated.
- the predetermined concentration was set to 50 ppm
- Leaf disc lesion area treated with any one of 4-27, 4-28, 4-29, 5-1, 5-2, 5-3, 5-4, 5-5, and 6-2 was 30% or less of the lesion area of untreated leaf discs.
- the resulting mixture was foliarly sprayed so as to sufficiently adhere to the foliage of the barley.
- the barley was air-dried, and one day later, an aqueous suspension of spores of barley net spot fungus was inoculated by spraying.
- the barley was placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 3 days, then cultivated in the greenhouse for 7 days, and then the lesion area was examined.
- the lesion area in barley treated with each compound of the present invention was 30% or less of the lesion area in untreated barley.
- Test Example 11 Prevention test against wheat rust (Puccinia recondita) A plastic pot was filled with soil, wheat (cultivar: Shirogane) was sown therein, and cultivated in a greenhouse for 9 days.
- the lesion area in the wheat treated with each compound of the present invention was 30% or less of the lesion area in the untreated wheat.
- Test Example 12 Control Test against Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, and wheat (variety: Apogee) was sown therein and cultivated in a greenhouse for 10 days.
- the wheat After spraying, the wheat was air-dried, and four days later, an aqueous suspension containing spores of the wheat leaf blight fungus was inoculated by spraying. After inoculation, the wheat was placed under high humidity at 18°C for 3 days, then cultivated under lighting for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the wheat treated with each compound of the present invention was 30% or less of the lesion area in the untreated wheat.
- Test Example 13 Control test against wheat leaf blight (Septoria tritici) Plastic pots were filled with soil, wheat (cultivar: Apogee) was sown there, cultivated in a greenhouse for 10 days, and wheat leaf blight spores were suspended in water. The liquid was spray inoculated. After inoculation, the wheat was placed under high humidity at 18° C. for 3 days, and then compounds 1-2, 2-1, 3-1, 4-2, and 4- of the present invention were formulated according to the method described in Formulation Example 1.
- Test Example 14 Prevention test against tomato late blight (Phytophthora infestans) Plastic pots were filled with soil, tomatoes (variety: patio) were seeded therein, and cultivated in a greenhouse for 20 days.
- the tomatoes After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying an aqueous suspension containing spores of Tomato Phytophthora. After inoculation, the tomatoes were placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 1 day, then cultivated in the greenhouse for 4 days, and then the lesion area was examined. As a result, the lesion area on tomatoes treated with the compounds of the present invention was 30% or less of the lesion area on untreated tomatoes.
- Test Example 15 Prevention test against soybean rust (Phakopsora pachyrhizi) Plastic pots were filled with soil, soybeans (cultivar: Kurosengoku) were sown therein, and grown in a greenhouse for 10 to 14 days.
- the soybeans After spraying, the soybeans were air-dried, and 2 to 5 days later, an aqueous suspension of soybean rust spores was inoculated by spraying. 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, then cultivated in the greenhouse for 12 days, and then the lesion area was examined. As a result, the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
- Test Example 16 Control test against soybean rust (Phakopsora pachyrhizi) Plastic pots were filled with soil, soybeans (cultivar: Kurosengoku) were sown there, grown in a greenhouse for 10 days, and water suspensions containing spores of soybean rust fungi were obtained. The suspension 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 day, and then cultivated in the greenhouse for 2 days.
- Test Example 17 Prevention test against soybean spot disease (Cercospora sojina) A plastic pot was filled with soil, soybeans (cultivar: Tachinagaha) were sown therein and grown in a greenhouse for 13 days. Compounds 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 4-4, 4-5 and 6 of the present invention formulated according to the method described in Formulation Example 1 -1, 1-7, 1-8, 1-9, 3-1, 3-2, 4-14, 4-16, 4-17, 4-19, 4-20, 4-21, 4-22 , 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-4, 5-5, 6-2, or 2-3 with a concentration of 200 ppm The resulting mixture was foliarly sprayed so that it adhered sufficiently to the leaves of the soybean.
- the soybeans After spraying, the soybeans were air-dried, and one day later, they were inoculated by spraying an aqueous suspension of spores of the soybean leaf spot 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 3 days, then cultivated in the greenhouse for 16 days, and then the lesion area was examined. As a result, the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
- Test Example 18 Prevention test against tomato ring spot (Alternaria solani) Plastic pots were filled with soil, tomatoes (variety: Patio) were sown therein, and grown in a greenhouse for 20 days.
- the tomatoes After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying an aqueous suspension of spores of tomato ring-blight fungus. After the inoculation, the tomato was placed at 18° C. and high humidity for 6 days, and then the lesion area was examined. As a result, the lesion area on tomatoes treated with the compounds of the present invention was 30% or less of the lesion area on untreated tomatoes.
- Test Example 19 Control test against bean sclerotinia (Sclerotinia sclerotiorum) Plastic pots were filled with soil, and bean beans (variety: long quail bean) were sown and grown in a greenhouse for 8 days.
- the green beans After spraying, the green beans were air-dried, and a PDA medium containing mycelia of Sclerotinia vulgaris was placed on the leaves of the green beans. After inoculation, all green beans were placed under high humidity only at night, and the area of lesions was examined 4 days after inoculation. As a result, the lesion area in the green beans treated with each compound of the present invention was 30% or less of the lesion area in the untreated green beans.
- Test method 20 Test against Aphis gossypii
- a test compound is prepared according to the method described in Formulation Example 1, water containing 0.03% by volume of a spreading agent is added, and a diluted solution containing a predetermined concentration of the test compound is added. to prepare.
- a cucumber (Cucumis sativus) seedling (second true leaf development stage) planted in a container is inoculated with about 30 Aphis gossypii (all stages). After 1 day, the seedlings are sprayed with the diluted solution at a rate of 10 mL/seedling. After another 5 days, the number of surviving insects is investigated, and the control value is determined by the following formula.
- Control value (%) ⁇ 1-(Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
- Cb Number of test insects in untreated area
- Cai Number of surviving insects in untreated area during survey
- Tb Number of test insects in treated area Tai: Surviving number of insects in treated area during survey
- Test example 20 As a result of testing according to Test Method 20 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, all of the compounds of the present invention exhibited a control value of 90% or more.
- Compounds of the present invention 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 6-1, 1-1, 1-6, 1-7, 1-9, 4- 1, 4-7, 4-9, 4-10, 4-11, 4-12, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-23, 4-24, 4-25, 4-29, 5-1, 6-2
- Test example 21 As a result of testing according to Test Method 21 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, all of the compounds of the present invention showed a mortality rate of 90% or more.
- Compounds of the present invention 1-2, 2-1, 3-1, 3-2, 6-1, 1-6, 1-7, 1-9, 2-2, 3-3, 4-7, 4- 14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-29, 6-2
- Test example 22 As a result of testing according to Test Method 22 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, all of the compounds of the present invention showed a mortality rate of 80% or more.
- Compounds of the present invention 3-1, 3-2, 4-2, 6-1, 4-7, 4-15, 4-18, 4-13, 1-7, 1-8, 1-9, 4- 14, 4-17, 4-29, 4-22, 4-23, 4-24, 4-25
- Test method 23 Test against two-spotted spider mite
- the test compound is prepared according to the method described in Formulation Example 1, and water containing 0.03% by volume of Syndyne (registered trademark) is added to dilute the test compound to a predetermined concentration. Prepare the liquid. Approximately 40 two-spotted spider mite female adults are released on kidney bean (Phaseolus vulgaris) seedlings (first true leaf development stage) planted in a container. After one day, the seedlings are sprayed with the diluted solution at a rate of 10 mL/seedling. After 13 days, the number of surviving insects is investigated, and the control value is calculated according to the following formula.
- Control value (%) ⁇ 1-(Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
- Cb Number of test insects in untreated area
- Cai Number of surviving insects in untreated area during survey
- Tb Number of test insects in treated area Tai: Surviving number of insects in treated area during survey
- Test example 23 As a result of testing according to Test Method 23 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, all of the compounds of the present invention exhibited a control value of 90% or more.
- Compounds of the present invention 1-2, 2-1, 3-1, 3-2, 4-2, 6-1, 1-3, 1-6, 2-2, 2-3, 3-3, 4- 7, 4-9, 4-10, 4-11, 4-15, 4-16, 4-17, 4-18, 4-19, 4-21, 4-22, 4-24, 4-25, 4-27, 4-29, 5-5
- the compound of the present invention has a controlling effect on pests and can be used for controlling pests.
Abstract
Description
本発明はフェニル酢酸誘導体、その用途及びその製造中間体に関する。
すなわち、本発明は以下のとおりである。
〔1〕 式(I):
X及びLの組合せは、
Xが窒素原子であり、Lが酸素原子又はNHである組合せ;又は、
XがCHであり、Lが酸素原子である組合せを表し、
nは、1又は2を表し、
Eは、群Aより選ばれる1以上の置換基で置換されていてもよいC6-C10アリール基、群Bより選ばれる1以上の置換基で置換されていてもよい5-10員芳香族複素環基、群Cより選ばれる1以上の置換基で置換されていてもよいC3-C7シクロアルケニル基、R3-O-N=C(R4)-、R5-C≡C-、又はR6O-を表し、
R1及びR2は、同一又は相異なり、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、メトキシ基、シクロプロピル基、又はハロゲン原子を表し、
R3は、群Gより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、又はR7CH2-を表し、
R4は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、又は水素原子を表し、
R5は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R6は、群Gより選ばれる1以上の置換基で置換されているメチル基、群Dより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又は群Eより選ばれる1以上の置換基で置換されていてもよいC3-C4シクロアルキル基を表し、
R7は、フェニル基、又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表す。
群A:C1-C6鎖式炭化水素基、C1-C3アルキルチオ基{該C1-C6鎖式炭化水素基及び該C1-C3アルキルチオ基は、群Gより選ばれる1以上の置換基で置換されていてもよい}、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、OR10、C(O)R8、C(O)OR8、C(O)NR8R9、NR8R9、C(R11)=N-OR12、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、及びニトロ基からなる群。
R8及びR9は、同一又は相異なり、群Gより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、又は水素原子を表し、
R10は、群Gより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R11は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、又は水素原子を表し、
R12は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C3鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、及び5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表す。
群B:群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C1-C6鎖式炭化水素基、C1-C3アルキルチオ基{該C1-C6鎖式炭化水素基及び該C1-C3アルキルチオ基は、群Gより選ばれる1以上の置換基で置換されていてもよい}、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、OR13、C(O)R8、C(O)OR8、C(O)NR8R9、NR8R9、C(R11)=N-OR12、ハロゲン原子、シアノ基、及びニトロ基からなる群。
R13は、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C1-C6鎖式炭化水素基{該C1-C6鎖式炭化水素基は、C3-C6シクロアルキル基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、又はトリフルオロメチル基を表す。
群C:C1-C4鎖式炭化水素基、C1-C3アルコキシ基{該C1-C4鎖式炭化水素基及び該C1-C3アルコキシ基は、1以上のハロゲン原子で置換されていてもよい}、ハロゲン原子、シアノ基、オキソ基、及び(=NOR13)からなる群。
群D:C1-C6アルコキシ基、C1-C6アルキルチオ基{該C1-C6アルコキシ基及び該C1-C6アルキルチオ基は、群Gより選ばれる1以上の置換基で置換されていてもよい}、C3-C6シクロアルキル基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基、及びヒドロキシ基からなる群。
群E:C1-C3鎖式炭化水素基、C1-C3アルコキシ基、C3-C6シクロアルキル基{該C1-C3鎖式炭化水素基、該C1-C3アルコキシ基、及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}、オキソ基、ハロゲン原子、シアノ基、及び(=NOR4)からなる群。
群F:C1-C3鎖式炭化水素基、C3-C6シクロアルキル基、C1-C3アルコキシ基、C1-C3アルキルチオ基{該C1-C3鎖式炭化水素基、該C3-C6シクロアルキル基、該C1-C3アルコキシ基、及び該C1-C3アルキルチオ基は、群Gより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基、及びヒドロキシ基からなる群。
群G:C3-C6シクロアルキル基、C1-C3アルコキシ基、及びハロゲン原子からなる群。〕
で示される化合物(以下、本発明化合物Nと記す)、若しくはそのNオキシド又はそれらの塩(以下、式(I)で示される化合物、若しくはそのNオキシド又はそれらの塩を、本発明化合物と記す)。
〔2〕 nが、1であり、
R1及びR2が、同一又は相異なり、1以上のハロゲン原子で置換されていてもよいC1-C3アルキル基、メトキシ基、又はハロゲン原子であり、
R2が、4位又は5位に結合し、
Eが、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、R3-O-N=C(R4)-、R5-C≡C-、R6O-、又はC5-C6シクロアルケニル基であり、
R3が、群Gより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC3-C6シクロアルキル基、又はR7CH2-であり、
R4が、C1-C3鎖式炭化水素基、又は水素原子であり、
R5が、C1-C6鎖式炭化水素基、又はC3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}であり、
R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基であり、
R7が、フェニル基又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Jより選ばれる1以上の置換基で置換されていてもよい}である、〔1〕に記載の化合物若しくはそのNオキシド又はそれらの塩。
群H:1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、C1-C3アルコキシ基、トリフルオロメトキシ基、C3-C4シクロアルキル基、ハロゲン原子、シアノ基、及びニトロ基からなる群。
群I:C3-C6シクロアルキル基、C1-C3アルコキシ基、フェニル基{該C1-C3アルコキシ基及び該フェニル基は、1以上のハロゲン原子で置換されていてもよい}、及びハロゲン原子からなる群。
群J:C1-C3鎖式炭化水素基、C1-C3アルコキシ基{該C1-C3鎖式炭化水素基及び該C1-C3アルコキシ基は、1以上のハロゲン原子で置換されていてもよい}、C3-C6シクロアルキル基、ハロゲン原子、シアノ基、及びニトロ基からなる群。
〔3〕 Eが、フェニル基、ピリジル基、チエニル基、チアゾリル基、ピラゾリル基{該フェニル基、該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、R5-C≡C-、R6O-、又はC5-C6シクロアルケニル基である、〔2〕に記載の化合物若しくはそのNオキシド又はそれらの塩。
〔4〕 〔1〕~〔3〕のいずれかに記載の化合物若しくはそのNオキシド又はそれらの塩と不活性担体とを含有する農薬組成物。
〔5〕 群(a)、群(b)、群(c)及び群(d)からなる群より選ばれる1以上の成分、並びに、〔1〕~〔3〕のいずれかに記載の化合物若しくはそのNオキシド又はそれらの塩を含有する組成物:
群(a):殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群;
群(b):殺菌活性成分;
群(c):植物成長調整成分;
群(d):忌避成分。
〔6〕 〔1〕~〔3〕のいずれかに記載の化合物若しくはそのNオキシド若しくはそれらの塩の有効量又は〔5〕に記載の組成物の有効量を植物又は土壌に処理することによる有害生物防除方法。
〔7〕 〔1〕~〔3〕のいずれかに記載の化合物若しくはそのNオキシド若しくはそれらの塩の有効量又は〔5〕に記載の組成物の有効量をダイズ又はダイズを生育する土壌に施用することによる、ミトコンドリアチトクロームbタンパク質にF129Lのアミノ酸置換を有するダイズさび病菌の防除方法。
〔8〕 有害生物を防除するための、〔1〕~〔3〕のいずれかに記載の化合物若しくはそのNオキシド若しくはそれらの塩又は〔5〕に記載の組成物の使用。
〔9〕 〔1〕~〔3〕のいずれかに記載の化合物若しくはそのNオキシド若しくはそれらの塩の有効量又は〔5〕に記載の組成物の有効量を保持している種子又は栄養生殖器官。
〔10〕 式(II):
X及びLの組合せは、
Xが窒素原子であり、Lが酸素原子又はNHである組合せ;又は、
XがCHであり、Lが酸素原子である組合せを表し、
Eaは、R12aC(O)-、R12aC(=N-OH)-、ヒドロキシ基、B(OH)2、4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル基、又はハロゲン原子を表し、
R1a及びR2aは、同一又は相異なり、メチル基、又はハロゲン原子を表し、
R12aは、C1-C3アルキル基、又は水素原子を表す。〕
で示される化合物(以下、中間体Aと記す)。
ハロゲン原子とは、フッ素原子、塩素原子、臭素原子、又はヨウ素原子を意味する。
置換基が2以上のハロゲン原子で置換されている場合、それらのハロゲン原子は各々同一でも異なっていてもよい。
置換基が特定の群(例えばC1-C3アルキル基及びハロゲン原子からなる群)より選ばれる2以上の基又は原子で置換されている場合、それらの基又は原子は各々同一であっても異なっていてもよい。
本明細書における「群Xより選ばれる1以上の置換基で置換されていてもよい」(XはA、B、C、D、E、F、G、H、I、J、およびKのいずれか1つを意味する)との表記は、群Xより選ばれる置換基が2つ以上存在する場合、それらの置換基は各々同一でも異なっていてもよい。
本明細書における「CX-CY」との表記は、炭素原子数がX乃至Yであることを意味する。例えば「C1-C6」との表記は、炭素原子数が1乃至6であることを意味する。
鎖式炭化水素基とは、アルキル基、アルケニル基又はアルキニル基を表す。
アルキル基としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、1,1-ジメチルプロピル基、1,2-ジメチルプロピル基、ブチル基、sec-ブチル基、tert-ブチル基、ペンチル基、ヘキシル基、及びデシル基が挙げられる。
アルケニル基としては、例えばビニル基、1-プロペニル基、2-プロペニル基、1-メチル-1-プロペニル基、1-メチル-2-プロペニル基、1,2-ジメチル-1-プロペニル基、3-ブテニル基、4-ペンテニル基、5-ヘキセニル基、及び9-デセニル基が挙げられる。
アルキニル基としては、例えばエチニル基、1-プロピニル基、2-プロピニル基、1-メチル-2-プロピニル基、1,1-ジメチル-2-プロピニル基、2-ブチニル基、4-ペンチニル基、5-ヘキシニル基、及び9-デシニル基が挙げられる。
アルキルチオ基としては、例えばメチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、ブチルチオ基、tert-ブチルチオ基、ペンチルチオ基、及びヘキシルチオ基が挙げられる。
シクロアルケニル基としては、例えばシクロペンテニル基及びシクロヘキセニル基が挙げられる。
芳香族複素環基としては、例えばピロリル基、フリル基、チエニル基、ピラゾリル基、イミダゾリル基、トリアゾリル基、テトラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、オキサジアゾリル基、チアジアゾリル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、テトラジニル基、インドリル基、インダゾリル基、ベンゾイミダゾリル基、イミダゾピリジル、ベンゾチオフェニル基、ベンゾフラニル基、キノリル基、イソキノリル基、キナゾリニル基、及びキノキサリニル基が挙げられる。
ミトコンドリアチトクロームbタンパク質にF129Lのアミノ酸置換を有するダイズさび病菌とは、ミトコンドリアチトクロームタンパク質をコードするミトコンドリアチトクロームb遺伝子中に変異を有し、該変異の結果としてF129Lのアミノ酸置換が起こったことにより、QoI殺菌剤に抵抗性を示すダイズさび病菌(学名:Phakopsora pachyrhizi)である。
幾何異性体としては、例えば以下の構造が挙げられる。
〔態様2〕態様1において、R3が、C1-C6鎖式炭化水素基{該C1-C6鎖式炭化水素基は、C3-C4シクロアルキル基及びハロゲン原子からなる群より選ばれる1以上の置換基で置換されていてもよい}、又はR7CH2-であり、R4が、メチル基又は水素原子であり、R7が、フェニル基又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Kより選ばれる1以上の置換基で置換されていてもよい}である化合物。
群K:1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、及びハロゲン原子からなる群。
〔態様3〕本発明化合物Nにおいて、EがR5-C≡C-である化合物。
〔態様4〕態様3において、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基である化合物。
〔態様5〕本発明化合物Nにおいて、EがR6O-である化合物。
〔態様6〕態様5において、R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基である化合物。
〔態様7〕本発明化合物Nにおいて、Eが群Aより選ばれる1以上の置換基で置換されていてもよいフェニル基である化合物。
〔態様8〕本発明化合物Nにおいて、Eが群Hより選ばれる1以上の置換基で置換されていてもよいフェニル基である化合物。
〔態様9〕本発明化合物Nにおいて、Eが群Bより選ばれる1以上の置換基で置換されていてもよい5-6員芳香族複素環基である化合物。
〔態様10〕本発明化合物Nにおいて、Eが群Hより選ばれる1以上の置換基で置換されていてもよい5-6員芳香族複素環基である化合物。
〔態様11〕本発明化合物Nにおいて、Eが、ピリジル基、チエニル基、チアゾリル基、又はピラゾリル基{該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}である化合物。
〔態様12〕本発明化合物Nにおいて、Eが、ピリジル基、チエニル基、チアゾリル基、又はピラゾリル基{該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Kより選ばれる1以上の置換基で置換されていてもよい}である化合物。
〔態様13〕本発明化合物Nにおいて、EがC5-C6シクロアルケニル基である化合物。
〔態様14〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、ピリジル基、チエニル基、チアゾリル基、ピラゾリル基{該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Kより選ばれる1以上の置換基で置換されていてもよい}、C5-C6シクロアルケニル基、R3-O-N=C(R4)-、R5-C≡C-、又はR6O-であり、R3が、C1-C6鎖式炭化水素基{該C1-C6鎖式炭化水素基は、C3-C4シクロアルキル基及びハロゲン原子からなる群より選ばれる1以上の置換基で置換されていてもよい}、又はR7CH2-であり、R4が、メチル基又は水素原子であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基であり、R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基であり、R7が、フェニル基又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Kより選ばれる1以上の置換基で置換されていてもよい}である化合物。
〔態様15〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Aより選ばれる1以上の置換基で置換されていてもよい}、5-6員芳香族複素環基{該5-6員芳香族複素環基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、群Cより選ばれる1以上の置換基で置換されていてもよいC3-C7シクロアルケニル基、R5-C≡C-、又はR6O-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}である化合物。
〔態様16〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、ピリジル基、チエニル基、チアゾリル基、ピラゾリル基{該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Kより選ばれる1以上の置換基で置換されていてもよい}、C5-C6シクロアルケニル基、R5-C≡C-、又はR6O-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基であり、R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基である化合物。
〔態様17〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Aより選ばれる1以上の置換基で置換されていてもよい}、5-6員芳香族複素環基{該5-6員芳香族複素環基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、R5-C≡C-、又はR6O-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}である化合物。
〔態様18〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、ピリジル基、チエニル基、チアゾリル基、ピラゾリル基{該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Kより選ばれる1以上の置換基で置換されていてもよい}、R5-C≡C-、又はR6O-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基であり、R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基である化合物。
〔態様19〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Aより選ばれる1以上の置換基で置換されていてもよい}、5-6員芳香族複素環基{該5-6員芳香族複素環基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、又はR5-C≡C-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}である化合物。
〔態様20〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、ピリジル基、チエニル基、チアゾリル基、ピラゾリル基{該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Kより選ばれる1以上の置換基で置換されていてもよい}、又はR5-C≡C-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基である化合物。
〔態様21〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Aより選ばれる1以上の置換基で置換されていてもよい}、5-6員芳香族複素環基{該5-6員芳香族複素環基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、又はR6O-である化合物。
〔態様22〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、ピリジル基、チエニル基、チアゾリル基、ピラゾリル基{該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Kより選ばれる1以上の置換基で置換されていてもよい}、又はR6O-であり、R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基である化合物。
〔態様23〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Aより選ばれる1以上の置換基で置換されていてもよい}、R5-C≡C-、又はR6O-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}である化合物。
〔態様24〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、R5-C≡C-、又はR6O-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基であり、R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基である化合物。
〔態様25〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Aより選ばれる1以上の置換基で置換されていてもよい}、又は5-6員芳香族複素環基{該5-6員芳香族複素環基は、群Hより選ばれる1以上の置換基で置換されていてもよい}である化合物。
〔態様26〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、ピリジル基、チエニル基、チアゾリル基、又はピラゾリル基{該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Kより選ばれる1以上の置換基で置換されていてもよい}である化合物。
〔態様27〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Aより選ばれる1以上の置換基で置換されていてもよい}、又はR5-C≡C-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}である化合物。
〔態様28〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、又はR5-C≡C-であり、R5が、C1-C6鎖式炭化水素基又はC3-C6シクロアルキル基である化合物。
〔態様29〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Aより選ばれる1以上の置換基で置換されていてもよい}、又はR6O-である化合物。
〔態様30〕本発明化合物Nにおいて、Eが、フェニル基{該フェニル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、又はR6O-であり、R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基である化合物。
〔態様31〕本発明化合物Nにおいて、XがCHであり、Lが酸素原子である化合物。
〔態様32〕態様1において、XがCHであり、Lが酸素原子である化合物。
〔態様33〕態様2において、XがCHであり、Lが酸素原子である化合物。
〔態様34〕態様3において、XがCHであり、Lが酸素原子である化合物。
〔態様35〕態様4において、XがCHであり、Lが酸素原子である化合物。
〔態様36〕態様5において、XがCHであり、Lが酸素原子である化合物。
〔態様37〕態様6において、XがCHであり、Lが酸素原子である化合物。
〔態様38〕態様7において、XがCHであり、Lが酸素原子である化合物。
〔態様39〕態様8において、XがCHであり、Lが酸素原子である化合物。
〔態様40〕態様9において、XがCHであり、Lが酸素原子である化合物。
〔態様41〕態様10において、XがCHであり、Lが酸素原子である化合物。
〔態様42〕態様11において、XがCHであり、Lが酸素原子である化合物。
〔態様43〕態様12において、XがCHであり、Lが酸素原子である化合物。
〔態様44〕態様13において、XがCHであり、Lが酸素原子である化合物。
〔態様45〕態様14において、XがCHであり、Lが酸素原子である化合物。
〔態様46〕態様15において、XがCHであり、Lが酸素原子である化合物。
〔態様47〕態様16において、XがCHであり、Lが酸素原子である化合物。
〔態様48〕態様17において、XがCHであり、Lが酸素原子である化合物。
〔態様49〕態様18において、XがCHであり、Lが酸素原子である化合物。
〔態様50〕態様19において、XがCHであり、Lが酸素原子である化合物。
〔態様51〕態様20において、XがCHであり、Lが酸素原子である化合物。
〔態様52〕態様21において、XがCHであり、Lが酸素原子である化合物。
〔態様53〕態様22において、XがCHであり、Lが酸素原子である化合物。
〔態様54〕態様23において、XがCHであり、Lが酸素原子である化合物。
〔態様55〕態様24において、XがCHであり、Lが酸素原子である化合物。
〔態様56〕態様25において、XがCHであり、Lが酸素原子である化合物。
〔態様57〕態様26において、XがCHであり、Lが酸素原子である化合物。
〔態様58〕態様27において、XがCHであり、Lが酸素原子である化合物。
〔態様59〕態様28において、XがCHであり、Lが酸素原子である化合物。
〔態様60〕態様29において、XがCHであり、Lが酸素原子である化合物。
〔態様61〕態様30において、XがCHであり、Lが酸素原子である化合物。
〔態様62〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1が、1以上のハロゲン原子で置換されていてもよいC1-C3アルキル基、メトキシ基、又はハロゲン原子である化合物。
〔態様63〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1が、メチル基、メトキシ基、又はハロゲン原子である化合物。
〔態様64〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1がメチル基である化合物。
〔態様65〕態様1~61、又は本発明化合物Nのいずれかにおいて、R2が、1以上のハロゲン原子で置換されていてもよいC1-C3アルキル基、メトキシ基、又はハロゲン原子である化合物。
〔態様66〕態様1~61、又は本発明化合物Nのいずれかにおいて、R2が、メチル基、メトキシ基、又はハロゲン原子である化合物。
〔態様67〕態様1~61、又は本発明化合物Nのいずれかにおいて、R2がメチル基である化合物。
〔態様68〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1及びR2が、同一又は相異なり、1以上のハロゲン原子で置換されていてもよいC1-C3アルキル基、メトキシ基、又はハロゲン原子である化合物。
〔態様69〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1が、メチル基、メトキシ基、又はハロゲン原子であり、R2が、1以上のハロゲン原子で置換されていてもよいC1-C3アルキル基、メトキシ基、又はハロゲン原子である化合物。
〔態様70〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1がメチル基であり、R2が、1以上のハロゲン原子で置換されていてもよいC1-C3アルキル基、メトキシ基、又はハロゲン原子である化合物。
〔態様71〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1及びR2が、同一又は相異なり、メチル基、メトキシ基、又はハロゲン原子である化合物。
〔態様72〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1がメチル基であり、R2が、メチル基、メトキシ基、又はハロゲン原子である化合物。
〔態様73〕態様1~61、又は本発明化合物Nのいずれかにおいて、R1及びR2が、メチル基である化合物。
〔態様74〕態様1~61、又は本発明化合物Nのいずれかにおいて、nが1である化合物。
〔態様75〕態様68において、nが1である化合物。
〔態様76〕態様69において、nが1である化合物。
〔態様77〕態様70において、nが1である化合物。
〔態様78〕態様71において、nが1である化合物。
〔態様79〕態様72において、nが1である化合物。
〔態様80〕態様73において、nが1である化合物。
〔態様81〕態様1~61、又は本発明化合物Nのいずれかにおいて、nが1であり、R2が、4位又は5位に結合している化合物。
〔態様82〕態様68において、nが1であり、R2が、4位又は5位に結合している化合物。
〔態様83〕態様69において、nが1であり、R2が、4位又は5位に結合している化合物。
〔態様84〕態様70において、nが1であり、R2が、4位又は5位に結合している化合物。
〔態様85〕態様71において、nが1であり、R2が、4位又は5位に結合している化合物。
〔態様86〕態様72において、nが1であり、R2が、4位又は5位に結合している化合物。
〔態様87〕態様73において、nが1であり、R2が、4位又は5位に結合している化合物。
〔態様88〕態様1~61、又は本発明化合物Nのいずれかにおいて、nが1であり、R2が4位に結合している化合物。
〔態様89〕態様68において、nが1であり、R2が4位に結合している化合物。
〔態様90〕態様69において、nが1であり、R2が4位に結合している化合物。
〔態様91〕態様70において、nが1であり、R2が4位に結合している化合物。
〔態様92〕態様71において、nが1であり、R2が4位に結合している化合物。
〔態様93〕態様72において、nが1であり、R2が4位に結合している化合物。
〔態様94〕態様73において、nが1であり、R2が4位に結合している化合物。
で示される化合物である。
態様88~94の化合物は、式(I-4)で示すこともできる。
式(A1)で示される化合物(以下、化合物(A1)と記す)は、式(B1)で示される化合物(以下、化合物(B1)と記す)と式(M1)で示される化合物(以下、化合物(M1)と記す)とをパラジウム触媒及び塩基の存在下で反応させることにより製造することができる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、ヘキサン、トルエン、キシレン等の炭化水素(以下、炭化水素類と記す);メチルtert-ブチルエーテル(以下、MTBEと記す)、テトラヒドロフラン(以下、THFと記す)、ジメトキシエタン等のエーテル(以下、エーテル類と記す);クロロホルム、クロロベンゼン等のハロゲン化炭化水素(以下、ハロゲン化炭化水素類と記す);ジメチルホルムアミド(以下、DMFと記す)、N-メチルピロリドン(以下、NMPと記す)等のアミド(以下、アミド類と記す);酢酸メチル、酢酸エチル等のエステル(以下、エステル類と記す);アセトニトリル、プロピオニトリル等のニトリル(以下、ニトリル類と記す);水及びこれらの2つ以上の混合物が挙げられる。
反応に用いられるパラジウム触媒としては、トリス(ジベンジリデンアセトン)ジパラジウム(0)(以下、Pd2(dba)3と記す)、テトラキス(トリフェニルホスフィン)パラジウム(0)(以下、Pd(PPh3)4と記す)、及び{1,1’-ビス(ジフェニルホスフィノ)フェロセン}パラジウム(II)ジクロリド(以下、PdCl2(dppf)と記す)等のパラジウム触媒が挙げられる。
反応に用いられる塩基としては例えば、トリエチルアミン、ピリジン等の有機塩基(以下、有機塩基類と記す);炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩(以下、アルカリ金属炭酸塩類と記す);炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属炭酸水素塩(以下、アルカリ金属炭酸水素塩類と記す);フッ化ナトリウム及びリン酸三カリウムが挙げられる。
反応には必要に応じて、配位子を用いてもよい。反応に用いられる配位子としては、トリフェニルホスフィン、キサントホス、2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル、1,1’-ビス(ジフェニルホスフィノ)フェロセン、2-ジシクロヘキシルホスフィノ-2’,4’,6’-トリイソプロピルビフェニル、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル、1,2-ビス(ジフェニルホスフィノ)エタン等が挙げられる。反応に配位子を用いる場合、化合物(B1)1モルに対して、配位子が通常0.01~1モルの割合で用いられる。
反応には、化合物(B1)1モルに対して、化合物(M1)が通常1~10モルの割合、パラジウム触媒が通常0.01~1モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は通常0~150℃の範囲内である。反応時間は通常0.1~120時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(A1)を単離することができる。
化合物(M1)は、公知であるか、公知の方法に準じて製造することができる。
化合物(A1)は、式(B2)で示される化合物(以下、化合物(B2)と記す)と式(M2)で示される化合物(以下、化合物(M2)と記す)とをパラジウム触媒及び塩基の存在下で反応させることにより製造することができる。
反応は、化合物(B1)に代えて化合物(M2)を用い、化合物(M1)に代えて化合物(B2)を用い、製造法Aに準じて実施することができる。
化合物(M2)は、公知であるか、公知の方法に準じて製造することができる。
式(A2)で示される化合物(以下、化合物(A2)と記す)は、化合物(B1)と式(M3)で示される化合物(以下、化合物(M3)と記す)とを金属触媒及び塩基の存在下で反応させることにより製造することができる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、及びこれらの2つ以上の混合物が挙げられる。
反応に用いられる金属触媒としては、例えば、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド及びヨウ化銅(I)が挙げられる。
反応に用いられる塩基としては例えば、有機塩基類が挙げられる。
反応には、化合物(B1)1モルに対して、化合物(M3)が通常1~10モルの割合、金属触媒が通常0.01~1モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は通常0~150℃の範囲内である。反応時間は通常0.1~120時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(A2)を単離することができる。
化合物(M3)は、公知であるか、公知の方法に準じて製造することができる。
式(A3)で示される化合物(以下、化合物(A3)と記す)は、式(B3)で示される化合物(以下、化合物(B3)と記す)と式(M4)で示される化合物(以下、化合物(M4)と記す)又はその塩とを反応させることにより製造することができる。
化合物(M4)の塩としては例えば、塩酸塩及び硫酸塩が挙げられる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、炭化水素類;エーテル類;ハロゲン化炭化水素類;アミド類;エステル類;ニトリル類;メタノール、エタノール等のアルコール(以下、アルコール類と記す);及びこれらの2つ以上の混合物が挙げられる。
反応には必要に応じて、塩基を加えてもよい。反応に用いられる塩基としては例えば、有機塩基類;アルカリ金属炭酸塩類;アルカリ金属炭酸水素塩類;水素化ナトリウム及びリン酸三カリウムが挙げられる。反応に塩基が用いられる場合、化合物(B3)1モルに対して、塩基は通常1~10モルの割合で用いられる。
反応には、化合物(B3)1モルに対して、化合物(M4)が通常1~10モルの割合で用いられる。
反応温度は通常0~150℃の範囲内である。反応時間は通常0.1~120時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(A3)を単離することができる。
また化合物(A3)は、国際公開第98/043949号等に記載の方法に準じて製造することもできる。
化合物(M4)は、公知であるか、公知の方法に準じて製造することができる。
化合物(A3)は、式(B4)で示される化合物(以下、化合物(B4)と記す)と式(M5)で示される化合物(以下、化合物(M5)と記す)とを塩基の存在下で反応させることにより製造することができる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの2つ以上の混合物が挙げられる。
塩基としては例えば、有機塩基、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩、水素化ナトリウム及びリン酸三カリウムが挙げられる。
反応には、化合物(B4)1モルに対して、化合物(M5)が通常1~10モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は通常-20~150℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(A3)を単離することができる。
化合物(M5)は、公知であるか、公知の方法に準じて製造することができる。
式(A4)で示される化合物(以下、化合物(A4)と記す)は、化合物(B1)と式(M6)で示される化合物(以下、化合物(M6)と記す)とを金属触媒及び塩基の存在下で反応させることにより製造することができる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、炭化水素類、アミド類、水及びこれらの2つ以上の混合物が挙げられる。
反応に用いられる金属触媒としては、ヨウ化銅(I)、臭化銅(I)、塩化銅(I)、酸化銅(I)、トリフルオロメタンスルホン酸銅(I)ベンゼン錯体、テトラキス(アセトニトリル)銅(I)ヘキサフルオロホスファート、2-チオフェンカルボン酸銅(I)等の銅触媒;及びビス(シクロオクタジエン)ニッケル(0)、塩化ニッケル(II)等のニッケル触媒が挙げられる。
塩基としては、例えば有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、フッ化ナトリウム及びリン酸三カリウムが挙げられる。
反応には必要に応じて、配位子及び/又はアルカリ金属ハロゲン化物を用いてもよい。
配位子としては、例えば、トリフェニルホスフィン、キサントホス、2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル、1,1’-ビス(ジフェニルホスフィノ)フェロセン、2-ジシクロヘキシルホスフィノ-2’,4’,6’-トリイソプロピルビフェニル、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル、1,2-ビス(ジフェニルホスフィノ)エタン、2,2’-ビピリジン、2-アミノエタノール、8-ヒドロキシキノリン、1,10-フェナントロリン、trans-1,2-シクロヘキサンジアミン、trans-N,N’-ジメチルシクロヘキサン-1,2-ジアミン、及びN,N’-ジメチルエチレンジアミンが挙げられる。反応に配位子が用いられる場合、化合物(B1)1モルに対して、配位子は通常0.01~1モルの割合で用いられる。
アルカリ金属ハロゲン化物としては、フッ化カリウム、フッ化ナトリウム、塩化リチウム、塩化ナトリウム等が挙げられる。反応にアルカリ金属ハロゲン化物が用いられる場合、化合物(B1)1モルに対して、アルカリ金属ハロゲン化物は通常0.1~5モルの割合で用いられる。
反応には、化合物(B1)1モルに対して、化合物(M6)が通常1~10モルの割合、金属触媒が通常0.01~2モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は、通常-20℃~200℃の範囲である。反応時間は通常0.1~48時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(A4)を得ることができる。
化合物(M6)は、公知であるか、公知の方法に準じて製造することができる。
式(A5)で示される化合物(以下、化合物(A5)と記す)は、式(B5)で示される化合物(以下、化合物(B5)と記す)と式(M7)で示される化合物(以下、化合物(M7)と記す)とを、ホスフィン類及びアゾジエステル類の存在下で反応させることにより製造することができる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類;エーテル類;ハロゲン化炭化水素類;アミド類;エステル類;ニトリル類及びこれらの2つ以上の混合物が挙げられる。
ホスフィン類としては、例えば、トリフェニルホスフィン及びトリメチルホスフィンが挙げられる。
アゾジエステル類としては、例えば、ジエチル アゾジカルボキシラート、ジイソプロピル アゾジカルボキシラート及びビス(2-メトキシエチル) アゾジカルボキシラートが挙げられる。
反応には、化合物(B5)1モルに対して、化合物(M7)が通常1~10モルの割合、ホスフィン類が通常1~10モルの割合、アゾジエステル類が通常1~10モルの割合で用いられる。
反応温度は通常0~150℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(A5)を単離することができる。
化合物(M7)は、公知であるか、公知の方法に準じて製造することができる。
化合物(A5)は、化合物(B5)と式(M8)で示される化合物(以下、化合物(M8)と記す)とを、塩基の存在下で反応させることにより製造することもできる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの2つ以上の混合物が挙げられる。
塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
反応には、化合物(B5)1モルに対して、化合物(M8)が通常1~10モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は通常-20~150℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(A5)を単離することができる。
化合物(M8)は、公知であるか、公知の方法に準じて製造することができる。
式(A6)で示される化合物(以下、化合物(A6)と記す)は、式(B6)で示される化合物(以下、化合物(B6)と記す)と式(M9)で示される化合物(以下、化合物(M9)と記す)とを塩基の存在下で反応させて式(B7)で示される化合物(以下、化合物(B7)と記す)を得る工程(以下、工程(I-1)と記す)、及び化合物(B7)と式(M10)で示される化合物(以下、化合物(M10)と記す)とを塩基の存在下で反応させる工程(以下、工程(I-2)と記す)により製造することができる。
反応に用いられる塩基としては、例えば、水素化ナトリウムが挙げられる。
反応には、化合物(B6)1モルに対して、化合物(M9)が通常1モル~10モルの割合、塩基が通常0.5モル~5モルの割合で用いられる。
反応時間は、通常5分間~72時間の範囲内である。反応温度は、通常-20℃~100℃の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(B7)を得ることができる。
化合物(M9)は、市販の化合物であるか、公知の方法に準じて製造することができる。
反応に用いられる塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、及び水素化ナトリウムが挙げられる。
反応には、化合物(B7)1モルに対して、化合物(M10)が通常1~10モルの割合、塩基が通常1~20モルの割合で用いられる。
反応温度は通常-20~100℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(A6)を単離することができる。
化合物(M10)は、市販の化合物であるか、公知の方法に準じて製造することができる。
式(A7)で示される化合物(以下、化合物(A7)と記す)は、式(B26)で示される化合物(以下、化合物(B26)と記す)と式(M12)で示される化合物(以下、化合物(M12)と記す)とを塩基の存在下で反応させて式(B9)で示される化合物(以下、化合物(B9)と記す)を得る工程(以下、工程(K-1)と記す)、及び化合物(B9)と化合物(M10)とを塩基の存在下で反応させる工程(以下、工程(K-2)と記す)により製造することができる。
反応に用いられる塩基としては、例えば、水素化ナトリウム;及びナトリウムメトキシド、ナトリウムエトキシド、カリウムt-ブトキシド等のアルカリ金属アルコキシド(以下、アルカリ金属アルコキシド類と記す)が挙げられる。
反応には、化合物(B6)1モルに対して、化合物(M12)が通常1モル~10モルの割合、塩基が通常1モル~5モルの割合で用いられる。
反応時間は、通常5分間~72時間の範囲内である。反応温度は、通常-20℃~100℃の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(B9)を得ることができる。
化合物(M12)は、市販の化合物であるか、公知の方法に準じて製造することができる。
式(A8)で示される化合物(以下、化合物(A8)と記す)は、式(B10)で示される化合物(以下、化合物(B10)と記す)と式(M13)で示される化合物(以下、化合物(M13)と記す)とを、触媒及び塩基の存在下で反応させることにより製造することができる。
反応は、化合物(B1)に代えて化合物(M13)を用い、化合物(M1)に代えて化合物(B10)を用いて、製造法Aに準じて実施することができる。
化合物(M13)は、公知の化合物であるか、公知の方法に準じて製造することができる。
式(I)で示される化合物のNオキシドは、式(I)で示される化合物と酸化剤とを反応させることにより製造することができる。反応は例えば米国特許出願公開第2018/0009778号明細書又は国際公開第2016/121970号に記載の方法に準じて実施することができる。
化合物(B7)は、化合物(B6)と式(M11)で示される化合物(以下、化合物(M11)と記す)とを反応させて式(B8)で示される化合物(以下、化合物(B8)と記す)を得る工程(以下、工程(1-1)と記す)、化合物(B8)を酸の存在下で反応させて化合物(B7)を得る工程(以下、工程(1-2)と記す)により製造することができる。
反応には、化合物(B6)1モルに対して、化合物(M11)が通常1モル~10モルの割合で用いられる。
反応時間は、通常5分間~72時間の範囲内である。反応温度は、通常-20℃~200℃の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより化合物(B8)を得ることができる。
化合物(M11)は、市販の化合物であるか、公知の方法に準じて製造することができる。
反応に用いられる酸としては例えば、塩酸、及び酢酸が挙げられる。
反応には、化合物(B8)1モルに対して、酸が通常1~10モルの割合、塩基が通常1~20モルの割合で用いられる。
反応温度は通常-20~100℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(B7)を単離することができる。
式(B16)で示される化合物(以下、化合物(B16)と記す)は、式(B11)で示される化合物(以下、化合物(B11)と記す)と式(M14)で示される化合物(以下、化合物(M14)と記す)とを触媒及び塩基の存在下で反応させて式(B12)で示される化合物(以下、化合物(B12)と記す)を得る工程(以下、工程(2-1)と記す)、化合物(B12)を塩基の存在下で反応させて式(B13)で示される化合物(以下、化合物(B13)と記す)を得る工程(以下、工程(2-2)と記す)、化合物(B13)と化合物(M11)とを反応させて式(B14)で示される化合物(以下、化合物(B14)と記す)を得る工程(以下、工程(2-3)と記す)、化合物(B14)を酸の存在下で反応させて式(B15)で示される化合物(以下、化合物(B15)と記す)を得る工程(以下、工程(2-4)と記す)、及び化合物(B15)と化合物(M10)とを塩基の存在下で反応させる工程(以下、工程(2-5)と記す)により製造することができる。
反応に用いられる触媒としては、例えば、酢酸パラジウム(II)、Pd2(dba)3、Pd(PPh3)4、及びPdCl2(dppf)等のパラジウム触媒;及びヨウ化銅(I)、臭化銅(I)、塩化銅(I)、酸化銅(I)、トリフルオロメタンスルホン酸銅(I)ベンゼンコンプレックス、テトラキス(アセトニトリル)銅(I)ヘキサフルオロホスファート、2-チオフェンカルボン酸銅(I)等の銅触媒が挙げられる。
反応に用いられる塩基としては、例えば、有機塩基類;アルカリ金属炭酸塩類;アルカリ金属炭酸水素塩類;リン酸三カリウム等のアルカリ金属リン酸塩(以下、アルカリ金属リン酸塩類と記す);及び酢酸ナトリウム等の酢酸塩(以下、酢酸塩類と記す)が挙げられる。
反応には必要に応じて、配位子を用いてもよい。反応に用いられる配位子としては、トリフェニルホスフィン、キサントホス、2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチル、1,1’-ビス(ジフェニルホスフィノ)フェロセン、2-ジシクロヘキシルホスフィノ-2’,4’,6’-トリイソプロピルビフェニル、2-ジシクロヘキシルホスフィノ-2’,6’-ジメトキシビフェニル、2-ジ-tert-ブチルホスフィノ-2’,4’,6’-トリイソプロピル-1,1’-ビフェニル、トリ-tert-ブチルホスフィン、1,2-ビス(ジフェニルホスフィノ)エタン、ピリジン-2-カルボン酸、(L)-プロリン、trans-1,2-シクロヘキサンジアミン、trans-N,N’-ジメチルシクロヘキサン-1,2-ジアミン、N,N’-ジメチルエチレンジアミン、N,N-ジメチルグリシン塩酸塩等が挙げられる。反応に配位子が用いられる場合、化合物(B11)1モルに対して、配位子は通常0.01~1モルの割合で用いられる。
反応には、化合物(B11)1モルに対して、化合物(M14)が通常0.1~10モルの割合、触媒が通常0.01~1モルの割合、塩基が通常1~10モルの割合で用いられる。
反応時間は、通常5分間~72時間の範囲である。反応温度は、通常-20℃~200℃の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(B12)を単離することができる。
化合物(M14)は、公知の化合物であるか、公知の方法に準じて製造することができる。
反応に用いられる塩基としては例えば、アルカリ金属リン酸塩類及びのアルカリ金属アルコキシド類が挙げられる。
反応には、化合物(B12)1モルに対して、塩基が通常1~20モルの割合で用いられる。
式(B18)で示される化合物(以下、化合物(B18)と記す)は、式(B27)で示される化合物(以下、化合物(B27)と記す)と化合物(M12)とを塩基の存在下で反応させて式(B17)で示される化合物(以下、化合物(B17)と記す)を得る工程(以下、工程(3-1)と記す)、及び化合物(B17)と化合物(M10)とを塩基の存在下で反応させる工程(以下、工程(3-2)と記す)により製造することができる。
化合物(B2)は、化合物(B1)とジボロン酸又はジボロン酸エステルとを塩基及びパラジウム触媒の存在下で反応させて製造することができる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類;エーテル類;ハロゲン化炭化水素類;アミド類;エステル類;ジメチルスルホキシド(以下、DMSOと記す)等のスルホキシド(以下、スルホキシド類と記す);ニトリル類及びこれらの2つ以上の混合物が挙げられる。
反応に用いられる塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、酢酸塩類、及びリン酸三カリウムが挙げられる。
パラジウム触媒としては、例えば、PdCl2(dppf)が挙げられる。
ジボロン酸又はジボロン酸エステルとしては、ビス(ピナコラト)ジボロン、テトラヒドロキシジボラン等が挙げられる。
反応には、化合物(B1)1モルに対して、ジボロン酸又はジボロン酸エステルが通常1~5モルの割合、塩基が通常1~5モルの割合、パラジウム触媒が通常0.01~0.5モルの割合で用いられる。
反応温度は通常0~150℃の範囲内であり、反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(B2)を単離することができる。
化合物(B5)は、化合物(B2)を酸化することにより製造することができる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、アルコール類、水及びこれらの2つ以上の混合物が挙げられる。
反応に用いられる酸化剤としては、例えば、メタクロロ過安息香酸及び過酸化水素水が挙げられる。
酸化剤として過酸化水素水を用いる場合は、必要に応じて塩基を加えてもよい。
塩基としては、水酸化ナトリウム及び水酸化カリウムが挙げられる。
反応には、化合物(B2)1モルに対して、酸化剤が通常1~5モルの割合で用いられる。
反応に塩基が用いられる場合、化合物(B2)1モルに対して、塩基は通常0.1~5モルの割合で用いられる。
反応温度は通常-20~120℃の範囲内であり、反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に水及びチオ硫酸ナトリウム等の還元剤を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(B5)を単離することができる。
化合物(B5)は、式(B19)で示される化合物(以下、化合物(B19)と記す)とジボロン酸又はジボロン酸エステルとを塩基及びパラジウム触媒の存在下で反応させて式(B20)で示される化合物(以下、化合物(B20)と記す)を得る工程(以下、工程(6-1)と記す)、及び化合物(B20)と化合物(M13)とを塩基及び金属触媒の存在下で反応させる工程(以下、工程(6-2)と記す)により製造することができる。
化合物(B19)は、公知の化合物であるか、公知の方法に準じて製造することができる。
式(B21)で示される化合物(以下、化合物(B21)と記す)は、化合物(B5)とトリフルオロ酢酸無水物とを塩基の存在下で反応させることにより製造することができる。
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの2つ以上の混合物が挙げられる。
塩基としては例えば、有機塩基類が挙げられる。
反応には、化合物(B5)1モルに対して、トリフルオロ酢酸無水物が通常1~10モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は通常-20~100℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
式(B22)で示される化合物は、化合物(B1)と式(M15)で示される化合物(以下、化合物(M15)と記す)とを反応させることにより製造することができる。
反応は、例えば国際公開第2016/123253号に記載の方法に準じて実施することができる。
化合物(M15)は、市販の化合物であるか、公知の方法に準じて製造することができる。
化合物(B4)は、化合物(B3)とヒドロキシルアミン又はその塩とを反応させることにより製造することができる。
ヒドロキシルアミンの塩としては例えば、塩酸塩及び硫酸塩が挙げられる。
反応は、化合物(M4)に代えてヒドロキシルアミン又はその塩を用い、製造法Dに準じて実施することができる。
式(B23)で示される化合物は、化合物(B1)とN-ホルミルサッカリンとをパラジウム触媒、配位子、トリエチルシラン及び塩基の存在下で反応させることにより製造することができる。
反応は、Angew.Chem.Int.Ed.,2013,52,8611-8615等に記載の方法に準じて実施することができる。
前記混用又は併用とは、本発明化合物と本成分とを、同時に、別々に又は時間間隔をおいて使用することを意味する。
本発明化合物と本成分とを同時に使用する場合、本発明化合物及び本成分が、それぞれ別個の製剤に含まれていてもよく、1つの製剤に含まれていてもよい。
本発明の1つの側面は、群(a)、群(b)、群(c)、及び群(d)からなる群より選ばれる1以上の成分(すなわち、本成分)、並びに本発明化合物を含有する組成物(以下、組成物Aと記す)である。
なお、SXの略号は、実施例に記載の化合物群SX1~SX259から選ばれるいずれか1つの本発明化合物を意味する。また、以下に記載する本成分はいずれも公知の成分であり、市販の製剤から得るか、公知の方法により製造することができる。本成分が微生物の場合は、菌寄託機関から入手することもできる。なお、括弧内の数字はCAS RN(登録商標)を表す。
アバメクチン(abamectin) + SX, アセフェート(acephate) + SX, アセキノシル(acequinocyl) + SX, アセタミプリド(acetamiprid) + SX, アセトプロール(acetoprole) + SX, アクリナトリン(acrinathrin) + SX, アシノナピル(acynonapyr) + SX, アフィドピロペン(afidopyropen) + SX, アフォキソラネル(afoxolaner) + SX, アラニカルブ(alanycarb) + SX, アルジカルブ(aldicarb) + SX, アレスリン(allethrin) + SX, アルファシペルメトリン(alpha-cypermethrin) + SX, アルファエンドスルファン(alpha-endosulfan) + SX, リン化アルミニウム(aluminium phosphide) + SX, アミトラズ(amitraz) + SX, アザジラクチン(azadirachtin) + SX, アザメチホス(azamethiphos) + SX, アジンホスエチル(azinphos-ethyl) + SX, アジンホスメチル(azinphos-methyl) + SX, アゾシクロチン(azocyclotin) + SX, Celastrus angulatus樹皮(bark of Celastrus angulatus) + SX, ベンダイオカルブ(bendiocarb) + SX, ベンフルトリン(benfluthrin) + SX, ベンフラカルブ(benfuracarb) + SX, ベンスルタップ(bensultap) + SX, ベンゾキシメート(benzoximate) + SX, ベンズピリモキサン(benzpyrimoxan) + SX, ベータシフルトリン(beta-cyfluthrin) + SX, べータシペルメトリン(beta-cypermethrin) + SX, ビフェナゼート(bifenazate) + SX, ビフェントリン(bifenthrin) + SX, ビオアレスリン(bioallethrin) + SX, ビオレスメトリン(bioresmethrin) + SX, ビストリフルロン(bistrifluron) + SX, ホウ砂(borax) + SX, ホウ酸(boric acid) + SX, ブロフラニリド(broflanilide) + SX, ブロモプロピレート(bromopropylate) + SX, ブプロフェジン(buprofezin) + SX, ブトカルボキシム(butocarboxim) + SX, ブトキシカルボキシム(butoxycarboxim) + SX, カズサホス(cadusafos) + SX, リン化カルシウム(calcium phosphide) + SX, カルバリル(carbaryl) + SX, カルボフラン(carbofuran) + SX, カルボスルファン(carbosulfan) + SX, カルタップ塩酸塩(cartap hydrochloride) + SX, カルタップ(cartap) + SX, キノメチオナート(chinomethionat) + SX, クロラントラニリプロール(chlorantraniliprole) + SX, クロルデン(chlordane) + SX, クロレトキシホス(chlorethoxyfos) + SX, クロルフェナピル(chlorfenapyr) + SX, クロルフェンビンホス(chlorfenvinphos) + SX, クロルフルアズロン(chlorfluazuron) + SX, クロルメホス(chlormephos) + SX, クロルピクリン(chloropicrin) + SX,
クロルピリホス(chlorpyrifos) + SX, クロルピリホスメチル(chlorpyrifos-methyl) + SX, クロマフェノジド(chromafenozide) + SX, クロフェンテジン(clofentezine) + SX, クロチアニジン(clothianidin) + SX, コンカナマイシンA(concanamycin A) + SX, クマホス(coumaphos) + SX, クリオライト(cryolite) + SX, シアノホス(cyanophos) + SX, シアントラニリプロール(cyantraniliprole) + SX, シクラニリプロール(cyclaniliprole) + SX, シクロブトリフルラム(cyclobutrifluram) + SX, シクロプロトリン(cycloprothrin) + SX, シクロキサプリド(cycloxaprid) + SX, シエノピラフェン(cyenopyrafen) + SX, cyetpyrafen + SX, シフルメトフェン(cyflumetofen) + SX, シフルトリン(cyfluthrin) + SX, シハロジアミド(cyhalodiamide) + SX, シハロトリン(cyhalothrin) + SX, シヘキサチン(cyhexatin) + SX, シペルメトリン(cypermethrin) + SX, シフェノトリン(cyphenothrin) + SX, シプロフラニリド(cyproflanilide) + SX, シロマジン(cyromazine) + SX, ダゾメット(dazomet) + SX, デルタメトリン(deltamethrin) + SX, ジメトン-S-メチル(demeton-S-methyl) + SX, ジアフェンチウロン(diafenthiuron) + SX, ダイアジノン(diazinon) + SX, ジクロルボス(dichlorvos) + SX, ジクロロメゾチアズ(dicloromezotiaz) + SX, ジコホル(dicofol) + SX, ジクロトホス(dicrotophos) + SX, ジフロビダジン(diflovidazin) + SX, ジフルベンズロン(diflubenzuron) + SX, ジメフルトリン(dimefluthrin) + SX, ジメトエート(dimethoate) + SX, ジメチルビンホス(dimethylvinphos) + SX, ジンプロピリダズ(dimpropyridaz) + SX, ジノテフラン(dinotefuran) + SX, 八ホウ酸二ナトリウム(disodium octaborate) + SX, ジスルホトン(disulfoton) + SX, DNOC(2-methyl-4,6-dinitrophenol) + SX, ドラメクチン(doramectin) + SX, セイヨウオシダ乾燥葉(dried leaves of Dryopteris filix-mas) + SX, エマメクチン安息香酸塩(emamectin-benzoate) + SX, エンペントリン(empenthrin) + SX, エンドスルファン(endosulfan) + SX, EPN(O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, イプシロンメトフルトリン(epsilon-metofluthrin) + SX, イプシロンモンフルオロトリン(epsilon-momfluorothrin) + SX, エスフェンバレレート(esfenvalerate) + SX, エチオフェンカルブ(ethiofencarb) + SX, エチオン(ethion) + SX, エチプロール(ethiprole) + SX, エトプロホス(ethoprophos) + SX, エトフェンプロックス(etofenprox) + SX, エトキサゾール(etoxazole) + SX, ニガヨモギ抽出物(extract of Artemisia absinthium) + SX, インドセンダン抽出物(extract of Azadirachta indica) + SX, Cassia nigricans抽出物(extract of Cassia nigricans) + SX, クリトリア・テルナテアの抽出物(extract of clitoria ternatea) + SX, ヒレハリソウ抽出物(extract of Symphytum officinale) + SX,
アリタソウ抽出物(extracts or simulated blend of Chenopodium ambrosioides) + SX, タンジー抽出物(extract of Tanacetum vulgare) + SX, セイヨウイラクサ抽出物(extract of Urtica dioica) + SX, ヤドリギ抽出物(extract of Viscum album) + SX, ファンフル(famphur) + SX, フェナミホス(fenamiphos) + SX, フェナザキン(fenazaquin) + SX, 酸化フェンブタスズ(fenbutatin oxide) + SX, フェニトロチオン(fenitrothion) + SX, フェンメゾジチアズ(fenmezoditiaz) + SX, フェノブカルブ(fenobucarb) + SX, フェノキシカルブ(fenoxycarb) + SX,
フェンプロパトリン(fenpropathrin) + SX, フェンピロキシメート(fenpyroximate) + SX, フェンチオン(fenthion) + SX, フェンバレレート(fenvalerate) + SX, フィプロニル(fipronil) + SX, フロメトキン(flometoquin) + SX, フロニカミド(flonicamid) + SX, フルアクリピリム(fluacrypyrim) + SX, フルアザインドリジン(fluazaindolizine) + SX, フルアズロン(fluazuron) + SX, フルベンジアミド(flubendiamide) + SX, フルクロルジニリプロール(fluchlordiniliprole) + SX, フルシクロクスロン(flucycloxuron) + SX, フルシトリネート(flucythrinate) + SX, フルエンスルホン(fluensulfone) + SX, フルフェンプロックス(flufenoprox) + SX, フルフェノクスロン(flufenoxuron) + SX, フルフィプロール(flufiprole) + SX, フルメトリン(flumethrin) + SX, フルペンチオフェノックス(flupentiofenox) + SX, フルピラジフロン(flupyradifurone) + SX, フルピリミン(flupyrimin) + SX, フルララネル(fluralaner) + SX, フルバリネート(fluvalinate) + SX, フルキサメタミド(fluxametamide) + SX, ホルメタネート(formetanate) + SX, ホスチアゼート(fosthiazate) + SX, フラメトリン(furamethrin) + SX, フラチオカルブ(furathiocarb) + SX, ガンマシハロトリン(gamma-cyhalothrin) + SX, GS-オメガ/カッパHXTX-Hv1aペプチド(GS-omega/kappa HXTX-Hv1a peptide) + SX, ハルフェンプロックス(halfenprox) + SX, ハロフェノジド(halofenozide) + SX, ヘプタフルトリン(heptafluthrin) + SX, ヘプテノホス(heptenophos) + SX, ヘキサフルムロン(hexaflumuron) + SX, ヘキシチアゾクス(hexythiazox) + SX, ホップベータ酸のカリウム塩(potassium salt of hop beta acid) + SX, ヒドラメチルノン(hydramethylnon) + SX, ヒドロプレン(hydroprene) + SX, イミシアホス(imicyafos) + SX, イミダクロプリド(imidacloprid) + SX, イミダクロチズ(imidaclothiz) + SX, イミプロトリン(imiprothrin) + SX, インダザピロキサメト(indazapyroxamet) + SX, インドキサカルブ(indoxacarb) + SX, イソシクロセラム(isocycloseram) + SX,
イソフェンホス(isofenphos) + SX, イソプロカルブ(isoprocarb) + SX, イソプロピルO-(メトキシアミノチオホスホリル) サリチラート(isopropyl-O-(methoxyaminothiophosphoryl) salicylate) + SX, イソキサチオン(isoxathion) + SX, イベルメクチン(ivermectin) + SX, カデスリン(kadethrin) + SX, カッパテフルトリン(kappa-tefluthrin) + SX, カッパビフェントリン(kappa-bifenthrin) + SX, キノプレン(kinoprene) + SX, ラムダシハロトリン(lambda-cyhalothrin) + SX, レノレマイシン(lenoremycin) + SX, レピメクチン(lepimectin) + SX, 石灰硫黄合剤(lime sulfur) + SX, ロチラネル(lotilaner) + SX, ルフェヌロン(lufenuron) + SX, マシン油(machine oil) + SX, マラチオン(malathion) + SX, メカルバム(mecarbam) + SX, メペルフルトリン(meperfluthrin) + SX, メタフルミゾン(metaflumizone) + SX, メタム(metam) + SX, メタミドホス(methamidophos) + SX, メチダチオン(methidathion) + SX, メチオカルブ(methiocarb) + SX, メソミル(methomyl) + SX, メトプレン(methoprene) + SX, メトキシクロル(methoxychlor) + SX, メトキシフェノジド(methoxyfenozide) + SX, 臭化メチル(methyl bromide) + SX, メトフルトリン(metofluthrin) + SX, メトルカルブ(metolcarb) + SX, メトキサジアゾン(metoxadiazone) + SX, メビンホス(mevinphos) + SX, ミルベメクチン(milbemectin) + SX, ミルベマイシンオキシム(milbemycin oxime) + SX, モンフルオロトリン(momfluorothrin) + SX, モノクロトホス(monocrotophos) + SX, モキシデクチン(moxidectin) + SX, ナレッド(naled) + SX, ニコフルプロール(nicofluprole) + SX, ニコチン(nicotine) + SX, 硫酸ニコチン(nicotine-sulfate) + SX, ニテンピラム(nitenpyram) + SX, ノバルロン(novaluron) + SX,
ノビフルムロン(noviflumuron) + SX, アメリカアリタソウ種子油(oil of the seeds of Chenopodium anthelminticum) + SX, オメトエート(omethoate) + SX, オキサミル(oxamyl) + SX, オキサゾスルフィル(oxazosulfyl) + SX, オキシジメトンメチル(oxydemeton-methyl) + SX, パラチオン(parathion) + SX, パラチオンメチル(parathion-methyl) + SX, ペルメトリン(permethrin) + SX, フェノトリン(phenothrin) + SX, フェントエート(phenthoate) + SX, ホレート(phorate) + SX, ホサロン(phosalone) + SX, ホスメット(phosmet) + SX, ホスファミドン(phosphamidon) + SX, ホスフィン(phosphine) + SX, ホキシム(phoxim) + SX, ピリミカーブ(pirimicarb) + SX, ピリミホスメチル(pirimiphos-methyl) + SX, プラレトリン(prallethrin) + SX, プロフェノホス(profenofos) + SX, プロフルトリン(profluthrin) + SX, プロパルギット(propargite) + SX, プロペタムホス(propetamphos) + SX, プロポキスル(propoxur) + SX, アルギニン酸プロピレングリコール(propylene glycol alginate) + SX, プロチオホス(prothiofos) + SX, ピフルブミド(pyflubumide) + SX, ピメトロジン(pymetrozine) + SX, ピラクロホス(pyraclofos) + SX, ピレトリン(pyrethrins) + SX, ピリダベン(pyridaben) + SX, ピリダリル(pyridalyl) + SX, ピリダフェンチオン(pyridaphenthion) + SX, ピリフルキナゾン(pyrifluquinazone) + SX, ピリミジフェン(pyrimidifen) + SX, ピリミノストロビン(pyriminostrobin) + SX, ピリプロール(pyriprole) + SX, ピリプロキシフェン(pyriproxyfen) + SX, キナルホス(quinalphos) + SX, レスメトリン(resmethrin) + SX, ロテノン(rotenone) + SX, リアノジン(ryanodine) + SX, サロラネル(sarolaner) + SX, セラメクチン(selamectin) + SX, シグマシペルメトリン(sigma-cypermethrin) + SX, シラフルオフェン(silafluofen) + SX, ホウ酸ナトリウム(sodium borate) + SX, メタホウ酸ナトリウム(sodium metaborate) + SX, スピドキサマト(spidoxamat) + SX, スピネトラム(spinetoram) + SX, スピノサド(spinosad) + SX, スピロジクロフェン(spirodiclofen) + SX, スピロメシフェン(spiromesifen) + SX, スピロピジオン(spiropidion) + SX, スピロテトラマト(spirotetramat) + SX, スルフルラミド(sulfluramid) + SX, スルホテップ(sulfotep) + SX, スルホキサフロル(sulfoxaflor) + SX, 硫黄(sulfur) + SX, フッ化スルフリル(sulfuryl fluoride) + SX, 吐酒石(tartar emetic) + SX, タウフルバリネート(tau-fluvalinate) + SX, テブフェノジド(tebufenozide) + SX, テブフェンピラド(tebufenpyrad) + SX, テブピリムホス(tebupirimfos) + SX, テフルベンズロン(teflubenzuron) + SX, テフルトリン(tefluthrin) + SX, テメホス(temephos) + SX, テルブホス(terbufos) + SX, アリタソウから抽出したテルペン成分(terpene constituents of the extract of chenopodium ambrosioides near ambrosioides) + SX,
テトラクロラントラニリプロール(tetrachlorantraniliprole) + SX, テトラクロルビンホス(tetrachlorvinphos) + SX, テトラジホン(tetradifon) + SX, テトラメトリン(tetramethrin) + SX, テトラメチルフルトリン(tetramethylfluthrin) + SX, テトラニリプロール(tetraniliprole) + SX, シータシペルメトリン(theta-cypermethrin) + SX, チアクロプリド(thiacloprid) + SX, チアメトキサム(thiamethoxam) + SX, チオシクラム(thiocyclam) + SX, チオジカルブ(thiodicarb) + SX, チオファノックス(thiofanox) + SX, チオメトン(thiometon) + SX, チオスルタップ二ナトリウム塩(thiosultap-disodium) + SX, チオスルタップ一ナトリウム塩(thiosultap-monosodium) + SX, チオキサザフェン(tioxazafen) + SX, トルフェンピラド(tolfenpyrad) + SX, トラロメトリン(tralomethrin) + SX, トランスフルトリン(transfluthrin) + SX, トリアザメート(triazamate) + SX, トリアゾホス(triazophos) + SX, トリクロルホン(trichlorfon) + SX, トリフルエンフロネート(trifluenfuronate) + SX, トリフルメゾピリム(triflumezopyrim) + SX, トリフルムロン(triflumuron) + SX, トリメタカルブ(trimethacarb) + SX, チクロピラゾフロル(tyclopyrazoflor) + SX, バミドチオン(vamidothion) + SX, スリナムニガキ木材抽出物(wood extract of Quassia amara) + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, キシリルカルブ(xylylcarb) + SX, ゼータシペルメトリン(zeta-cypermethrin) + SX, リン化亜鉛(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, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX, (2Z)-2-({2-fluoro-4-methyl-5-[(R)-(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (2377084-09-6) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX,
1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX,
BT作物のタンパク質Cry1Ab (BT crop protein Cry1Ab) + SX, BT作物のタンパク質Cry1Ac (BT crop protein Cry1Ac) + SX, BT作物のタンパク質Cry1Fa (BT crop protein Cry1Fa) + SX, BT作物のタンパク質Cry1A.105 (BT crop protein Cry1A.105) + SX, BT作物のタンパク質Cry2Ab (BT crop protein Cry2Ab) + SX, BT作物のタンパク質Vip3A (BT crop protein Vip3A) + SX, BT作物のタンパク質mCry3A (BT crop protein mCry3A) + SX, BT作物のタンパク質Cry3Ab (BT crop protein Cry3Ab) + SX, BT作物のタンパク質Cry3Bb (BT crop protein Cry3Bb) + SX, BT作物のタンパク質Cry34Ab1/Cry35Ab1 (BT crop protein Cry34Ab1/Cry35Ab1) + SX, アドクソフィエス・オラナ顆粒病ウイルスBV-0001株(Adoxophyes orana granulosis virus strain BV-0001) + SX, アンチカルシア・ゲマタリス核多角体病ウイルス(Anticarsia gemmatalis mNPV) + SX, オートグラファ・カリフォルニア核多角体病ウイルス(Autographa californica mNPV) + SX, シジア・ポモネラ顆粒病ウイルスV15株(Cydia pomonella GV strain V15) + SX, シジア・ポモネラ顆粒病ウイルスV22株(Cydia pomonella GV strain V22) + SX, クリプトフレビア・ロイコトレタ顆粒病ウイルス(Cryptophlebia leucotreta GV) + SX, デンドロリムス・プンクタタス細胞質多面体ウイルス(Dendrolimus punctatus cypovirus) + SX, ヘリコベルパ・アルミゲラ核多角体病ウイルスBV-0003株(Helicoverpa armigera NPV strain BV-0003) + SX, ヘリコベルパ・ゼア核多角体病ウイルス(Helicoverpa zea NPV) + SX, リュマントリア・ディスパル核多角体病ウイルス(Lymantria dispar NPV) + SX, マメストラ・ブラシカエ核多角体病ウイルス(Mamestra brassicae NPV) + SX, マメストラ・コンフィグラタ核多角体病ウイルス(Mamestra configurata NPV) + SX, ネオディプリオン・アビエンティス核多角体病ウイルス(Neodiprion abietis NPV) + SX, ネオディプリオン・レコンテイ核多角体病ウイルス(Neodiprion lecontei NPV) + SX, ネオディプリオン・セルティファー核多角体病ウイルス(Neodiprion sertifer NPV) + SX, ノゼマ・ロクスタエ(Nosema locustae) + SX, オルギイア・プソイドツガタ核多角体病ウイルス(Orgyia pseudotsugata NPV) + SX, ピエリス・ラパエ顆粒病ウイルス(Pieris rapae GV) + SX, プロジア・インテルプンクテラ顆粒病ウイルス(Plodia interpunctella GV) + SX, スポドプテラ・エクシグア核多角体病ウイルス(Spodoptera exigua mNPV) + SX, スポドプテラ・リットラリス核多角体病ウイルス(Spodoptera littoralis mNPV) + SX, スポドプテラ・リツラ核多角体病ウイルス(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 rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5/F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。
アシベンゾラルSメチル(acibenzolar-S-methyl) + SX, アルジモルフ(aldimorph) + SX, アメトクトラジン(ametoctradin) + SX, アミノピリフェン(aminopyrifen) + SX, アミスルブロム(amisulbrom) + SX, アニラジン(anilazine) + SX, アザコナゾール(azaconazole) + SX, アゾキシストロビン(azoxystrobin) + SX, 塩基性硫酸銅(basic copper sulfate) + SX, ベナラキシル(benalaxyl) + SX, ベナラキシルM(benalaxyl-M) + SX, ベノダニル(benodanil) + SX, ベノミル(benomyl) + SX, ベンチアバリカルブ(benthiavalicarb) + SX, ベンチアバリカルブイソプロピル(benthiavalicarb-isopropyl) + SX, ベンゾビンジフルピル(benzovindiflupyr) + SX, ビナパクリル(binapacryl) + SX, ビフェニル(biphenyl) + SX, ビテルタノール(bitertanol) + SX, ビキサフェン(bixafen) + SX, ブラストサイジンS(blasticidin-S) + SX, ボルドー液(Bordeaux mixture) + SX, ボスカリド(boscalid) + SX, ブロモタロニル(bromothalonil) + SX, ブロムコナゾール(bromuconazole) + SX, ブピリメート(bupirimate) + SX, キャプタホール(captafol) + SX, キャプタン(captan) + SX, カルベンダジム(carbendazim) + SX, カルボキシン(carboxin) + SX, カルプロパミド(carpropamid) + SX, キノメチオナート(chinomethionat) + SX, キチン(chitin) + SX, クロロインコナジド(chloroinconazide) + SX, クロロネブ(chloroneb) + SX, クロロタロニル(chlorothalonil) + SX, クロゾリネート(chlozolinate) + SX, コレトクロリンB(colletochlorin B) + SX, 酢酸銅(II) (copper(II) acetate) + SX, 水酸化銅(II) (copper(II) hydroxide) + SX, 塩基性塩化銅(copper oxychloride) + SX, 硫酸銅(II) (copper(II) sulfate) + SX, クモキシストロビン(coumoxystrobin) + SX, シアゾファミド(cyazofamid) + SX, シフルフェナミド(cyflufenamid) + SX, シモキサニル(cymoxanil) + SX, シプロコナゾール(cyproconazole) + SX, シプロジニル(cyprodinil) + SX, ジクロベンチアゾクス(dichlobentiazox) + SX, ジクロフルアニド(dichlofluanid) + SX, ジクロシメット(diclocymet) + SX, ジクロメジン(diclomezine) + SX, ジクロラン(dicloran) + SX, ジエトフェンカルブ(diethofencarb) + SX, ジフェノコナゾール(difenoconazole) + SX, ジフルメトリム(diflumetorim) + SX, ジメタクロン(dimethachlone) + SX, ジメチリモール(dimethirimol) + SX, ジメトモルフ(dimethomorph) + SX, ジモキシストロビン(dimoxystrobin) + SX, ジニコナゾール(diniconazole) + SX, ジニコナゾールM(diniconazole-M) + SX, ジノカップ(dinocap) + SX, 亜リン酸水素二カリウム(dipotassium hydrogenphosphite) + SX, ジピメチトロン(dipymetitrone) + SX,
ジチアノン(dithianon) + SX, ドデシルベンゼンスルホン酸ビスエチレンジアミン銅(II)錯塩(dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt) + SX, ドデモルフ(dodemorph) + SX, ドジン(dodine) + SX, エジフェンホス(edifenphos) + SX, エノキサストロビン(enoxastrobin) + SX, エポキシコナゾール(epoxiconazole) + SX, エタコナゾール(etaconazole) + SX, エタボキサム(ethaboxam) + SX, エチリモール(ethirimol) + SX, エトリジアゾール(etridiazole) + SX, ティーツリー抽出物(extract of Melaleuca alternifolia) + SX, オオイタドリ抽出物(extract of Reynoutria sachalinensis) + SX, ハウチワマメ苗木の子葉の抽出物(extract of the cotyledons of lupine plantlets ("BLAD")) + SX, ニンニク抽出物(extract of Allium sativum) + SX, スギナ抽出物(extract of Equisetum arvense) + SX, キンレンカ抽出物(extract of Tropaeolum majus) + SX, ファモキサドン(famoxadone) + SX, フェンアミドン(fenamidone) + SX, フェナミンストロビン(fenaminstrobin) + SX, フェナリモル(fenarimol) + SX, フェンブコナゾール(fenbuconazole) + SX, フェンフラム(fenfuram) + SX, フェンヘキサミド(fenhexamid) + SX, フェノキサニル(fenoxanil) + SX, フェンピクロニル(fenpiclonil) + SX, フェンピコキサミド(fenpicoxamid) + SX, フェンプロピジン(fenpropidin) + SX, フェンプロピモルフ(fenpropimorph) + SX, フェンピラザミン(fenpyrazamine) + SX, 酢酸トリフェニル錫(fentin acetate) + SX, 塩化トリフェニル錫(fentin chloride) + SX, 水酸化トリフェニル錫(fentin hydroxide) + SX, フェルバム(ferbam) + SX, フェリムゾン(ferimzone) + SX, フロリルピコキサミド(florylpicoxamid) + SX, フルアジナム(fluazinam) + SX, フルベネテラム(flubeneteram) + SX, フルジオキソニル(fludioxonil) + SX, フルフェノキサジアザム(flufenoxadiazam) + SX, フルフェノキシストロビン(flufenoxystrobin) + SX, フルインダピル(fluindapyr) + SX, フルメチルスルホリム(flumetylsulforim) + SX, フルモルフ(flumorph) + SX, フルオピコリド(fluopicolide) + SX, フルオピラム(fluopyram) + SX, フルオピモミド(fluopimomide) + SX, フルオルイミド(fluoroimide) + SX, フルオキサピプロリン(fluoxapiprolin) +SX, フルオキサストロビン(fluoxastrobin) + SX, フルオキシチオコナゾール(fluoxytioconazole) + SX, フルキンコナゾール(fluquinconazole) + SX, フルシラゾール(flusilazole) + SX, フルスルファミド(flusulfamide) + SX, フルチアニル(flutianil) + SX, フルトラニル(flutolanil) + SX, フルトリアホール(flutriafol) + SX, フルキサピロキサド(fluxapyroxad) + SX, ホルペット(folpet) + SX, ホセチル(fosetyl) + SX,
ホセチルアルミニウム(fosetyl-aluminium) + SX, フベリダゾール(fuberidazole) + SX, フララキシル(furalaxyl) + SX, フラメトピル(furametpyr) + SX, グアザチン(guazatine) + SX, ヘキサコナゾール(hexaconazole) + SX, ヒメキサゾール(hymexazole) + SX, イマザリル(imazalil) + SX,
イミベンコナゾール(imibenconazole) + SX, イミノクタジン(iminoctadine) + SX, イミノクタジン酢酸塩(iminoctadine triacetate) + SX, インピルフルキサム(inpyrfluxam) + SX, ヨードカルブ(iodocarb) + SX, イプコナゾール(ipconazole) + SX, イプフェントリフルコナゾール(ipfentrifluconazole) + SX, イプフルフェノキン(ipflufenoquin) + SX, イプロベンホス(iprobenfos) + SX, イプロジオン(iprodione) + SX, イプロバリカルブ(iprovalicarb) + SX, イソフェタミド(isofetamid) + SX, イソフルシプラム(isoflucypram) + SX, イソプロチオラン(isoprothiolane) + SX, イソピラザム(isopyrazam) + SX, イソチアニル(isotianil) + SX, カスガマイシン(kasugamycin) + SX, クレソキシムメチル(kresoxim-methyl) + SX, ラミナリン(laminarin) + SX, オークの葉及び樹皮(leaves and bark of Quercus) + SX, マンコゼブ(mancozeb) + SX, マンデストロビン(mandestrobin) + SX, マンジプロパミド(mandipropamid) + SX, マンネブ(maneb) + SX, メフェントリフルコナゾール(mefentrifluconazole) + SX, メパニピリム(mepanipyrim) + SX, メプロニル(mepronil) + SX, メプチルジノカップ(meptyldinocap) + SX, メタラキシル(metalaxyl) + SX, メタラキシルM(metalaxyl-M) + SX, メタリルピコキサミド(metarylpicoxamid) + SX, メトコナゾール(metconazole) + SX, メタスルホカルブ(methasulfocarb) + SX, メチラム(metiram) + SX, メトミノストロビン(metominostrobin) + SX, メトラフェノン(metrafenone) + SX, メチルテトラプロール(metyltetraprole) + SX, ミクロブタニル(myclobutanil) + SX, ナフチフィン(naftifine) + SX, ヌアリモール(nuarimol) + SX, オクチリノン(octhilinone) + SX, オフラセ(ofurace) + SX, オリサストロビン(orysastrobin) + SX, オキサジキシル(oxadixyl) + SX, オキサチアピプロリン(oxathiapiprolin) + SX, oxine-copper + SX, オキソリニック酸(oxolinic acid) + SX, オキスポコナゾール(oxpoconazole) + SX, オキスポコナゾールフマル酸塩(oxpoconazole fumarate) + SX, オキシカルボキシン(oxycarboxin) + SX, オキシテトラサイクリン(oxytetracycline) + SX, ペフラゾエート(pefurazoate) + SX, ペンコナゾール(penconazole) + SX, ペンシクロン(pencycuron) + SX, ペンフルフェン(penflufen) + SX, ペンチオピラド(penthiopyrad) + SX, フェナマクリル(phenamacril) + SX, 亜リン酸(phosphorous acid) + SX, フサライド(phthalide) + SX, ピカルブトラゾクス(picarbutrazox) + SX, ピコキシストロビン(picoxystrobin) + SX,
ピペラリン(piperalin) + SX, ポリオキシン(polyoxins) + SX, 炭酸水素カリウム(potassium hydrogencarbonate) + SX, 亜リン酸二水素カリウム(potassium dihydrogenphosphite) + SX, プロベナゾール(probenazole) + SX, プロクロラズ(prochloraz) + SX, プロシミドン(procymidone) + SX, プロパミジン(propamidine) + SX, プロパモカルブ(propamocarb) + SX, プロピコナゾール(propiconazole) + SX, プロピネブ(propineb) + SX, プロキナジド(proquinazid) + SX, プロチオカルブ(prothiocarb) + SX, プロチオコナゾール(prothioconazole) + SX, ピジフルメトフェン(pydiflumetofen) + SX, ピラクロストロビン(pyraclostrobin) + SX, ピラメトストロビン(pyrametostrobin) + SX, ピラオキシストロビン(pyraoxystrobin) + SX, ピラプロポイン(pyrapropoyne) + SX, ピラジフルミド(pyraziflumid) + SX, ピラゾホス(pyrazophos) + SX, ピリベンカルブ(pyribencarb) + SX, ピリブチカルブ(pyributicarb) + SX, ピリダクロメチル(pyridachlometyl) + SX, ピリフェノックス(pyrifenox) + SX, ピリメタニル(pyrimethanil) + SX, ピリモルフ(pyrimorph) + SX, ピリオフェノン(pyriofenone) + SX, ピリソキサゾール(pyrisoxazole) + SX, ピロキロン(pyroquilon) + SX, キラヤ科植物抽出物(Quillaja extract) + SX, キンコナゾール(quinconazole) + SX, キノフメリン(quinofumelin) + SX, キノキシフェン(quinoxyfen) + SX, キントゼン(quintozene) + SX, キヌアのサポニン(Saponins of Chenopodium quinoa) + SX, セボクチラミン(seboctylamine) + SX, セダキサン(sedaxane) + SX, シルチオファム(silthiofam) + SX, シメコナゾール(simeconazole) + SX, 炭酸水素ナトリウム(sodium hydrogencarbonate) + SX, スピロキサミン(spiroxamine) + SX, ストレプトマイシン(streptomycin) + SX, 硫黄(sulfur) + SX, テブコナゾール(tebuconazole) + SX, テブフロキン(tebufloquin) + SX, テクロフタラム(teclofthalam) + SX, テクナゼン(tecnazene) + SX, テルビナフィン(terbinafine) + SX, テトラコナゾール(tetraconazole) + SX, チアベンダゾール(thiabendazole) + SX, チフルザミド(thifluzamide) + SX, チオファネート(thiophanate) + SX, チオファネートメチル(thiophanate-methyl) + SX, チウラム(thiram) + SX, チモール(thymol) + SX,
チアジニル(tiadinil) + SX, トルクロホスメチル(tolclofos-methyl) + SX, トルフェンピラド(tolfenpyrad) + SX, トルプロカルブ(tolprocarb) + SX, トリルフルアニド(tolylfluanid) + SX, トリアジメホン(triadimefon) + SX, トリアジメノール(triadimenol) + SX, トリアゾキシド(triazoxide) + SX, トリクロピリカルブ(triclopyricarb) + SX, トリシクラゾール(tricyclazole) + SX, トリデモルフ(tridemorph) + SX, トリフロキシストロビン(trifloxystrobin) + SX, トリフルミゾール(triflumizole) + SX, トリホリン(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-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX,
N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX,
methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX,
2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide(2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX,
(1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX,
N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX,
4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX,
6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 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,
Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo(商標) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB/BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002/AQ30002 + SX, Bacillus subtilis strain QST30004/AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON/M/91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX,
Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。
1-メチルシクロプロペン(1-methylcyclopropene) + SX, 1,3-ジフェニルウレア(1,3-diphenylurea) + SX, 2,3,5-トリヨード安息香酸(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-アミノレブリン酸塩酸塩(5-aminolevulinic acid hydrochloride) + SX, 6-ベンジルアミノプリン(6-benzylaminopurine) + SX, アブシシン酸(abscisic acid) + SX, AVG (aminoethoxyvinylglycine) + SX, アニシフルプリン(anisiflupurin) + SX, アンシミドール(ancymidol) + SX, ブトルアリン(butralin) + SX, 炭酸カルシウム(calcium carbonate) + SX, 塩化カルシウム(calcium chloride) + SX, ギ酸カルシウム(calcium formate) + SX, 過酸化カルシウム(calcium peroxide) + SX, 石灰硫黄(calcium polysulfide) + SX, 硫酸カルシウム(calcium sulfate) + SX, クロルメコートクロリド(chlormequat-chloride) + SX, クロロプロファム(chlorpropham) + SX, 塩化コリン(choline chloride) + SX, クロプロップ(cloprop) + SX, シアナミド(cyanamide) + SX, シクラニリド(cyclanilide) + SX, ダミノジッド(daminozide) + SX, デカン-1-オール(decan-1-ol) + SX, ジクロルプロップ(dichlorprop) + SX, ジケグラック(dikegulac) + SX, ジメチピン(dimethipin) + SX, ジクワット(diquat) + SX, エテホン(ethephon) + SX, エチクロゼート(ethychlozate) + SX, フルメトラリン(flumetralin) + SX, フルルプリミドール(flurprimidol) + SX, ホルクロルフェヌロン(forchlorfenuron) + SX,
ホルモノネチン(formononetin) + SX, ジベレリンA(Gibberellin A) + SX, ジベレリンA3(Gibberellin A3) + SX, イナベンフィド(inabenfide) + SX, カイネチン(Kinetin) + SX, lipochitooligosaccharide SP104 + SX, マレイン酸ヒドラジド(maleic hydrazide) + SX, メフルイジド(mefluidide) + SX, メピコートクロリド(mepiquat-chloride) + SX, 酸化型グルタチオン(oxidized glutathione) + SX, パクロブトラゾール(paclobutrazol) + SX, ペンディメタリン(pendimethalin) + SX, プロヘキサジオンカルシウム(prohexadione-calcium) + SX, プロヒドロジャスモン(prohydrojasmon) + SX, ピラフルフェンエチル(pyraflufen-ethyl) + SX, シントフェン(sintofen) + SX, 1-ナフタレン酢酸ナトリウム(sodium 1-naphthaleneacetate) + SX, シアン酸ナトリウム(sodium cyanate) + SX, チジアズロン(thidiazuron) + SX, トリアペンテノール(triapenthenol) + SX, トリブホス(tribufos) + SX, トリネキサパックエチル(trinexapac-ethyl) + SX, ウニコナゾールP (uniconazole-P) + SX, 2-(ナフタレン-1-イル)アセトアミド(2-(naphthalen-1-yl)acetamide) + SX, [4-オキソ-4-(2-フェニルエチル)アミノ]酪酸 + SX, 5-(トリフルオロメチル)ベンゾ[b]チオフェン-2-カルボン酸メチル + SX, 3-[(6-クロロ-4-フェニルキナゾリン-2-イル)アミノ]プロパン-1-オール + 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。
アントラキノン(anthraquinone) + SX, ディート(deet) + SX, イカリジン(icaridin) + SX。
コムギの病害:うどんこ病(Blumeria graminis)、赤かび病(Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale)、黄さび病(Puccinia striiformis)、黒さび病(Puccinia graminis)、赤さび病(Puccinia recondita)、紅色雪腐病(Microdochium nivale、Microdochium majus)、雪腐小粒菌核病(Typhula incarnata、Typhula ishikariensis)、裸黒穂病(Ustilago tritici)、なまぐさ黒穂病(Tilletia caries、Tilletia controversa)、眼紋病(Pseudocercosporella herpotrichoides)、葉枯病(Septoria tritici)、ふ枯病(Stagonospora nodorum)、黄斑病(Pyrenophora tritici-repentis)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)、立枯病(Gaeumannomyces graminis)、いもち病(Pyricularia graminis-tritici);
オオムギの病害:うどんこ病(Blumeria graminis)、赤かび病(Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale)、黄さび病(Puccinia striiformis)、黒さび病(Puccinia graminis)、小さび病(Puccinia hordei)、裸黒穂病(Ustilago nuda)、雲形病(Rhynchosporium secalis)、網斑病(Pyrenophora teres)、斑点病(Cochliobolus sativus)、斑葉病(Pyrenophora graminea)、ラムラリアリーフスポット病(Ramularia collo-cygni)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani);
トウモロコシの病害:さび病(Puccinia sorghi)、南方さび病(Puccinia polysora)、すす紋病(Setosphaeria turcica)、熱帯性さび病(Physopella zeae)、ごま葉枯病(Cochliobolus heterostrophus)、炭疽病(Colletotrichum graminicola)、グレーリーフスポット病(Cercospora zeae-maydis)、褐斑病(Kabatiella zeae)、ファエオスファエリアリーフスポット病(Phaeosphaeria maydis)、Diplodia病(Stenocarpella maydis、Stenocarpella macrospora)、ストークロット病(Fusarium graminearum、Fusarium verticilioides、Colletotrichum graminicola)、黒穂病(Ustilago maydis)、フイソデルマ病(Physoderma maydis)、tar spot病(Phyllachora maydis);
ワタの病害:炭疽病(Colletotrichum gossypii)、白かび病(Ramularia areola)、黒斑病(Alternaria macrospora、Alternaria gossypii)、Black root rot病 (Thielaviopsis basicola);
コーヒーの病害:さび病(Hemileia vastatrix)、リーフスポット病(Cercospora coffeicola);
ナタネの病害:菌核病(Sclerotinia sclerotiorum)、黒斑病(Alternaria brassicae)、根朽病(Phoma lingam)、light leaf spot病(Pyrenopeziza brassicae);
サトウキビの病害:さび病(Puccinia melanocephela、Puccinia kuehnii)、黒穂病 (Ustilago scitaminea);
ヒマワリの病害:さび病(Puccinia helianthi)、べと病(Plasmopara halstedii);
カンキツ類の病害:黒点病(Diaporthe citri)、そうか病(Elsinoe fawcetti)、緑かび病(Penicillium digitatum)、青かび病(Penicillium italicum)、疫病(Phytophthora parasitica、Phytophthora citrophthora)、こうじかび病(Aspergillus niger);
リンゴの病害:モニリア病(Monilinia mali)、腐らん病(Valsa ceratosperma)、うどんこ病(Podosphaera leucotricha)、斑点落葉病(Alternaria alternata apple pathotype)、黒星病(Venturia inaequalis)、炭疽病(Glomerella cingulata、Colletotrichum acutatum)、褐斑病(Diplocarpon mali)、輪紋病(Botryosphaeria berengeriana)、疫病(Phytophtora cactorum)、赤星病(Gymnosporangium juniperi-virginianae、Gymnosporangium yamadae);
ナシの病害:黒星病(Venturia nashicola、Venturia pirina)、黒斑病(Alternaria alternata Japanese pear pathotype)、赤星病(Gymnosporangium haraeanum);
モモの病害:灰星病(Monilinia fructicola)、黒星病(Cladosporium carpophilum)、ホモプシス腐敗病(Phomopsis sp.)、縮葉病(Taphrina deformans);
ブドウの病害:黒とう病(Elsinoe ampelina)、晩腐病(Glomerella cingulata、Colletotrichum acutatum)、うどんこ病(Uncinula necator)、さび病(Phakopsora ampelopsidis)、ブラックロット病(Guignardia bidwellii)、べと病(Plasmopara viticola);
カキの病害:炭疽病(Gloeosporium kaki、Colletotrichum acutatum)、落葉病(Cercospora kaki、Mycosphaerella nawae);
イチジクの病害:さび病(Phakopsora nishidana);
ウリ類の病害:炭疽病(Colletotrichum lagenarium)、うどんこ病(Sphaerotheca fuliginea)、つる枯病(Didymella bryoniae)、褐斑病(Corynespora cassiicola)、つる割病(Fusarium oxysporum)、べと病(Pseudoperonospora cubensis)、疫病(Phytophthora capsici)、苗立枯病(Pythium sp.);
トマトの病害:輪紋病(Alternaria solani)、葉かび病(Cladosporium fulvum)、すすかび病(Pseudocercospora fuligena)、疫病(Phytophthora infestans)、うどんこ病(Leveillula taurica);
ナスの病害:褐紋病(Phomopsis vexans)、うどんこ病(Erysiphe cichoracearum);
アブラナ科野菜の病害:黒斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、根こぶ病(Plasmodiophora brassicae)、べと病(Peronospora parasitica)、白さび病(Albugo candida);
ネギの病害:さび病(Puccinia allii);
ダイズの病害:紫斑病(Cercospora kikuchii)、黒とう病(Elsinoe glycines)、黒点病(Diaporthe phaseolorum var. sojae)、さび病(Phakopsora pachyrhizi)、褐色輪紋病(Corynespora cassiicola)、炭疽病(Colletotrichum glycines、Colletotrichum truncatum)、葉腐病(Rhizoctonia solani)、褐紋病(Septoria glycines)、斑点病(Cercospora sojina)、菌核病(Sclerotinia sclerotiorum)、うどんこ病(Microsphaera diffusa)、茎疫病(Phytophthora sojae)、べと病(Peronospora manshurica)、突然死病(Fusarium virguliforme)、黒根腐病(Calonectria ilicicola)、Diaporthe/Phomopsis complex(Diaporthe longicolla);
インゲンの病害:菌核病(Sclerotinia sclerotiorum)、さび病(Uromyces appendiculatus)、角斑病(Phaeoisariopsis griseola)、炭疽病(Colletotrichum lindemuthianum)、根腐病(Fusarium solani);
ラッカセイの病害:黒渋病(Cercospora personata)、褐斑病(Cercospora arachidicola)、白絹病(Sclerotium rolfsii)、黒根腐病(Calonectria ilicicola);
エンドウの病害:うどんこ病(Erysiphe pisi)、根腐病(Fusarium solani);
ジャガイモの病害:夏疫病(Alternaria solani)、疫病(Phytophthora infestans)、緋色腐敗病(Phytophthora erythroseptica)、粉状そうか病(Spongospora subterranea f. sp. subterranea)、半身萎凋病(Verticillium albo-atrum、Verticillium dahliae、Verticillium nigrescens)、乾腐病(Fusarium solani)、がん腫病(Synchytrium endobioticum);
イチゴの病害:うどんこ病(Sphaerotheca humuli);
チャの病害:網もち病(Exobasidium reticulatum)、白星病(Elsinoe leucospila)、輪斑病(Pestalotiopsis sp.)、炭疽病(Colletotrichum theae-sinensis);
タバコの病害:赤星病(Alternaria longipes)、炭疽病(Colletotrichum tabacum)、べと病(Peronospora tabacina)、疫病(Phytophthora nicotianae);
テンサイの病害:褐斑病(Cercospora beticola)、葉腐病(Thanatephorus cucumeris)、根腐病(Thanatephorus cucumeris)、黒根病(Aphanomyces cochlioides)、さび病(Uromyces betae);
バラの病害:黒星病(Diplocarpon rosae)、うどんこ病(Sphaerotheca pannosa);
キクの病害:褐斑病(Septoria chrysanthemi-indici)、白さび病(Puccinia horiana);
タマネギの病害:白斑葉枯病(Botrytis cinerea、Botrytis byssoidea、Botrytis squamosa)、灰色腐敗病(Botrytis allii)、小菌核性腐敗病(Botrytis squamosa);
種々の作物の病害:灰色かび病(Botrytis cinerea)、菌核病(Sclerotinia sclerotiorum)、黒腐菌核病(Sclerotium cepivorum)、苗立枯病(Pythium aphanidermatum、Pythium irregulare、Pythium ultimum);
ダイコンの病害:黒斑病(Alternaria brassicicola);
シバの病害:ダラースポット病(Sclerotinia homoeocarpa)、ブラウンパッチ病、ラージパッチ病(Rhizoctonia solani)、赤焼病(Pythium aphanidermatum);
バナナの病害:シガトカ病(Mycosphaerella fijiensis、Mycosphaerella musicola);
レンズマメの病害:Ascochyta病(Ascochyta lentis);
ヒヨコマメの病害:Ascochyta病(Ascochyta rabiei);
ピーマンの病害:炭疽病(Colletotrichum scovillei);
マンゴーの病害:炭疽病(Colletotrichum acutatum);
果樹の病害:白紋羽病(Rosellinia necatrix)、紫紋羽病(Helicobasidium mompa);
収穫後のリンゴ、ナシ等の果実の病害:ムコールロット病(Mucor piriformis);
Aspergillus属、Penicillium属、Fusarium属、Gibberella属、Tricoderma属、Thielaviopsis属、Rhizopus属、Mucor属、Corticium属、Phoma属、Rhizoctonia属、Diplodia属等によって引き起こされる、種子病害又は生育初期の病害;
ウイルス病:Olpidium brassicaeによって媒介されるレタスのビッグベイン病、Polymyxa属(例えば、Polymyxa betae及びPolymyxa graminis)によって媒介される各種作物のウイルス病;
細菌(bacteria)が引き起こす病害:イネの苗立枯細菌病(Burkholderia plantarii)、イネの内穎褐変病(Pantoea ananatis)、イネの白葉枯病(Xanthomonas oryzae pv. oryzae.)、キュウリの斑点細菌病(Pseudomonas syringae pv. lachrymans)、ナスの青枯病(Ralstonia solanacearum)、カンキツのかいよう病(Xanthomonas citri)、ハクサイの軟腐病(Erwinia carotovora)、ジャガイモのそうか病(Streptomyces scabiei)、トウモロコシのGoss's wilt病(Clavibacter michiganensis)、ブドウ、オリーブ、モモ等のピアス病(Xylella fastidiosa)、リンゴ、モモ、サクランボ等のバラ科植物の根頭がんしゅ病(Agrobacterium tumefaciens)。
ブドウネアブラムシ(Daktulosphaira vitifoliae)、ピーカンフィロキセラ(Phylloxera devastatrix)、ピーカンリーフフィロキセラ (Phylloxera notabilis)、サウザンピーカンリーフフィロキセラ(Phylloxera russelae)等のネアブラムシ科(Phylloxeridae);ツガカサアブラムシ(Adelges tsugae)、バルサムウーリーアフィッド(Adelges piceae)、ヒメカサアブラムシ(Aphrastasia pectinatae)等のカサアブラムシ科(Adelgidae);イネクロカメムシ(Scotinophara lurida)、ブラックパディーバグ(Scotinophara coarctata)、アオクサカメムシ(Nezara antennata)、トゲシラホシカメムシ(Eysarcoris aeneus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)、ムラサキシラホシカメムシ(Eysarcoris annamita)、クサギカメムシ(Halyomorpha halys)、ミナミアオカメムシ(Nezara viridula)、ブラウンスティンクバグ(Euschistus heros)、レッドバンデッドスティンクバグ(Piezodorus guildinii)、Oebalus pugnax、Dichelops melacanthus等のカメムシ科(Pentatomidae);Scaptocoris castanea等のツチカメムシ科(Cydnidae);ホソヘリカメムシ(Riptortus clavatus)、クモヘリカメムシ(Leptocorisa chinensis)、ホソクモヘリカメムシ(Leptocorisa acuta)等のホソヘリカメムシ科(Alydidae);ホソハリカメムシ(Cletus punctiger)、アシビロヘリカメムシ(Leptoglossus australis)等のヘリカメムシ科(Coreidae);カンシャコバネナガカメムシ(Cavelerius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus)、アメリカコバネナガカメムシ(Blissus leucopterus)等のナガカメムシ科(Lygaeidae);アカヒゲホソミドリカスミカメ(Trigonotylus caelestialium)、アカスジカスミカメ(Stenotus rubrovittatus)、フタトゲムギカスミカメ(Stenodema calcarata)、サビイロカスミカメ(Lygus lineolaris)等のカスミカメムシ科(Miridae);オンシツコナジラミ(Trialeurodes vaporariorum)、タバココナジラミ(Bemisia tabaci)、ミカンコナジラミ(Dialeurodes citri)、ミカントゲコナジラミ(Aleurocanthus spiniferus)、チャトゲコナジラミ(Aleurocanthus camelliae)、ヒサカキワタフキコナジラミ(Pealius euryae)等のコナジラミ科(Aleyrodidae);シュロマルカイガラムシ(Abgrallaspis cyanophylli)、アカマルカイガラムシ(Aonidiella aurantii)、ナシマルカイガラムシ(Diaspidiotus perniciosus)、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ヤノネカイガラムシ(Unaspis yanonensis)、ニセヤノネカイガラムシ(Unaspis citri)等のマルカイガラムシ科(Diaspididae);ルビーロウムシ(Ceroplastes rubens)等のカタカイガラムシ科(Coccidae);イセリアカイガラムシ(Icerya purchasi)、キイロワタフキカイガラムシ(Icerya seychellarum)等のワタフキカイガラムシ科(Margarodidae);ナスコナガイガラムシ(Phenacoccus solani)、クロテンコナカイガラムシ(Phenacoccus solenopsis)、フジコナカイガラムシ(Planococcus kraunhiae)、クワコナカイガラムシ(Pseudococcus comstocki)、ミカンコナカイガラムシ(Planococcus citri)、ガハニコナカイガラムシ(Pseudococcus calceolariae)、ナガオコナカイガラムシ(Pseudococcus longispinus)、タトルミーリーバグ(Brevennia rehi)等のコナカイガラムシ科(Pseudococcidae);ミカンキジラミ(Diaphorina citri)、ミカントガリキジラミ(Trioza erytreae)、ナシキジラミ(Cacopsylla pyrisuga)、チュウゴクナシキジラミ(Cacopsylla chinensis)、ジャガイモトガリキジラミ(Bactericera cockerelli)、ピアプシラ(Cacopsylla pyricola)等のキジラミ科(Psyllidae);プラタナスグンバイ(Corythucha ciliata)、アワダチソウグンバイ(Corythucha marmorata)、ナシグンバイ(Stephanitis nashi)、ツツジグンバイ(Stephanitis pyrioides)等のグンバイムシ科(Tingidae);トコジラミ(Cimex lectularius)、ネッタイトコジラミ(Cimex hemipterus)等のトコジラミ科(Cimicidae);Quesada gigas等のセミ科(Cicadidae);ブラジルサシガメ(Triatoma infestans)、オオサシガメ(Triatoma rubrofasciata)、Triatoma dimidiata、ベネズエラサシガメ(Rhodonius prolixus)等のサシガメ科(Reduviidae)。
チャノホソガ(Caloptilia theivora)、キンモンホソガ(Phyllonorycter ringoniella)等のホソガ科(Gracillariidae);モモシンクイガ(Carposina sasakii)等のシンクイガ科(Carposinidae);コーヒーリーフマイナー(Leucoptera coffeella)、モモハモグリガ(Lyonetia clerkella)、ギンモンハモグリガ(Lyonetia prunifoliella)等のハモグリガ科(Lyonetiidae);マイマイガ(Lymantria dispar)等のリマントリア属(Lymantria spp.)、チャドクガ(Euproctis pseudoconspersa)等のユープロクティス属(Euproctis spp.)等のドクガ科(Lymantriidae);コナガ(Plutella xylostella)等のコナガ科(Plutellidae);モモキバガ(Anarsia lineatella)、イモキバガ(Helcystogramma triannulella)、ワタアカミムシガ(Pectinophora gossypiella)、ジャガイモガ(Phthorimaea operculella)、Tuta absoluta等のキバガ科(Gelechiidae);アメリカシロヒトリ(Hyphantria cunea)等のヒトリガ科(Arctiidae);ジャイアントシュガーケーンボーラー(Telchin licus)等のカストニアガ科(Castniidae);ヒメボクトウ(Cossus insularis)等のボクトウガ科(Cossidae);ヨモギエダシャク(Ascotis selenaria)等のシャクガ科(Geometridae);ヒロヘリアオイラガ(Parasa lepida)等のイラガ科(Limacodidae);カキノヘタムシガ(Stathmopoda masinissa)等のニセマイコガ科(Stathmopodidae);クロメンガタスズメ(Acherontia lachesis)等のスズメガ科(Sphingidae);キクビスカシバ(Nokona feralis)、コスカシバ(Synanthedon hector)、ヒメコスカシバ(Synanthedon tenuis)等のスカシバガ科(Sesiidae);イネツトムシ(Parnara guttata)等のセセリチョウ科(Hesperiidae);イガ(Tinea translucens)、コイガ(Tineola bisselliella)等のヒロズコガ科(Tineidae)。
コクヌストモドキ(Tribolium castaneum)、ヒラタコクヌストモドキ(Tribolium confusum)、ガイマイゴミムシダマシ(Alphitobius diaperinus)等のゴミムシダマシ科(Tenebrionidae);ニジュウヤホシテントウ(Epilachna vigintioctopunctata)等のテントウムシ科(Coccinellidae);ヒラタキクイムシ(Lyctus brunneus)、コナナガシンクイ(Rhizopertha dominica)等のナガシンクイムシ科(Bostrychidae);ヒョウホンムシ科(Ptinidae);ゴマダラカミキリ(Anoplophora malasiaca)、Migdolus fryanus、クビアカツヤカミキリ(Aromia bungii)等のカミキリムシ科(Cerambycidae);オキナワカンシャクシコメツキ(Melanotus okinawensis)、トビイロムナボソコメツキ(Agriotes fuscicollis)、クシコメツキ(Melanotus legatus)、アシブトコメツキ属(Anchastus spp.)、コノデルス属(Conoderus spp.)、クテニセラ属(Ctenicera spp.)、リモニウス属(Limonius spp.)、アエオルス属(Aeolus spp.)等のコメツキムシ科(Elateridae);アオバアリガタハネカクシ(Paederus fuscipes)等のハネカクシ科(Staphylinidae);ヒメマルカツオブシムシ(Anthrenus verbasci)、ハラジロカツオブシムシ(Dermestes maculates)、ヒメアカカツオブシムシ(Trogoderma granarium)等のカツオブシムシ科(Dermestidae);タバコシバンムシ(Lasioderma serricorne)、ジンサンシバンムシ(Stegobium paniceum)等のシバンムシ科(Anobiidae);アカチビヒラタムシ(Cryptolestes ferrugineus)等のチビヒラタムシ科(Laemophloeidae);ノコギリヒラタムシ(Oryzaephilus surinamensis)等のホソヒラタムシ科(Silvanidae)、ブロッサムビートル(Brassicogethes aeneus)等のケシキスイムシ科(Nitidulidae)。
ホソツメダニ(Cheyletus eruditus)、クワガタツメダニ(Cheyletus malaccensis)、ミナミツメダニ(Chelacaropsis moorei)、イヌツメダニ(Cheyletiella yasguri)等のツメダニ科(Cheyletidae);ヒツジキュウセンヒゼンダニ(Psoroptes ovis)、ウマキュウセンヒゼンダニ(Psoroptes equi)、Knemidocoptes mutans、ミミヒゼンダニ(Otodectes cynotis)、ショクヒヒゼンダニ属(Chorioptes spp.)等のキュウセン科(Psoroptidae);ネコショウセンコウヒゼンダニ(Notoedres cati)、ネズミショウセンコウヒゼンダニ(Notoedres muris)、センコウヒゼンダニ(Sarcoptes scabiei)等のヒゼンダニ科(Sarcoptidae);ウサギズツキダニ(Listrophorus gibbus)等のズツキダニ科(Listrophoridae);ワクモ(Dermanyssus gallinae)等のサシダニ科(Dermanyssidae);トリサシダニ(Ornithonyssus sylviarum)、イエダニ(Ornithonyssus bacoti)等のオオサシダニ科(Macronyssidae)、ミツバチヘギイタダニ(Varroa jacobsoni)等のヘギイタダニ科(Varroidae)、イヌニキビダニ(Demodex canis)、ネコニキビダニ(Demodex cati)等のニキビダニ科(Demodicidae)、アカツツガムシ(Leptotrombidium akamushi)、フトゲツツガムシ(Leptotrombidium pallidum)、タテツツガムシ(Leptotrombidium scutellare)等のツツガムシ科(Trombiculidae)。
オビヤスデ目(Polydesmida):ヤケヤスデ(Oxidus gracilis)、アカヤスデ(Nedyopus tambanus)等のヤケヤスデ科(Paradoxosomatidae)。
等脚目(Isopoda):オカダンゴムシ(Armadillidium vulgare)等のオカダンゴムシ科(Armadillidiidae)。
唇脚綱(Chilopoda):ゲジ(Thereuonema hilgendorfi)等のゲジ科(Scutigeridae);トビズムカデ(Scolopendra subspinipes)等のオオムカデ科(Scolopendridae);イッスンムカデ(Bothropolys rugosus)等のイッスンムカデ科(Ethopolyidae)。
腹足綱(Gastropoda):チャコウラナメクジ(Limax marginatus)、キイロコウラナメクジ(Limax flavus)等のコウラナメクジ科(Limacidae);ナメクジ(Meghimatium bilineatum)等のナメクジ科(Philomycidae);スクミリンゴガイ(Pomacea canaliculata)等のリンゴガイ科(Ampullariidae);ヒメモノアラガイ(Austropeplea ollula)等のモノアラガイ科(Lymnaeidae)。
これらの製剤には本発明化合物又は組成物Aが重量比で通常0.0001~99%含有される。
組成物Aを種子又は栄養生殖器官に処理する場合、組成物Aを1つの製剤として種子又は栄養生殖器官に処理することもできるし、組成物Aを異なる複数の製剤として複数回に分けて種子又は栄養生殖器官に処理することもできる。組成物Aを異なる複数の製剤として複数回に分けて処理する方法としては、例えば、有効成分として本発明化合物のみを含む製剤を処理し、種子又は栄養生殖器官を風乾させた後、本成分を含む製剤を処理する方法;及び、有効成分として本発明化合物及び本成分を含む製剤を処理し、種子又は栄養生殖器官を風乾させた後、処理済みの本成分以外の本成分を含む製剤を処理する方法、が挙げられる。
本発明における本発明化合物又は組成物Aを保持している種子又は栄養生殖器官とは、種子又は栄養生殖器官の表面に、本発明化合物又は組成物Aが付着している状態のものを意味する。上記の本発明化合物又は組成物Aを保持している種子又は栄養生殖器官は、種子又は栄養生殖器官へ本発明化合物又は組成物Aが付着される前後に、本発明化合物又は組成物A以外の資材が付着されていてもよい。
また、組成物Aが種子又は栄養生殖器官の表面に層となって付着している場合、該層は、1つの層又は複数の層からなる。また、複数の層からなる場合、各々の層は、1以上の有効成分を含んでいる層であるか、又は、1以上の有効成分を含んでいる層と有効成分を含んでいない層とからなる。
本発明化合物又は組成物Aを保持している種子又は栄養生殖器官は、例えば、本発明化合物又は組成物A含む製剤を前記の種子処理の方法により、種子又は栄養生殖器官に施用することによって得ることができる。
カラム:L-column2 ODS、内径4.6mm、長さ30mm、粒子径3μm(一般財団法人化学物質評価研究機構)
UV測定波長:254nm
移動相:A液:0.1%ギ酸水溶液、B液:0.1%ギ酸アセトニトリル
流速:2.0mL/分
ポンプ:LC-20AD(島津製作所製)2台(高圧グラジエント)
グラジエント条件:[表LC1]に記載の濃度勾配で送液する。
検出器:LCMS-2020(島津製作所製)
イオン化法:DUIS
窒素雰囲気下で1,5-ジブロモ-2,4-ジメチルベンゼン1.06g、アセト酢酸メチル1.03g、酢酸パラジウム(II)0.09g、2-ジ-tert-ブチルホスフィノ-2’,4’,6’-トリイソプロピルビフェニル0.17g、リン酸三カリウム2.55g、及びトルエン20mLの混合物を還流下で2時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体1-1を0.71g得た。
0.30gの中間体1-1、THF2mL及びメタノール2mLの混合物に、28%ナトリウムメトキシドメタノール溶液0.3mLを加え、60℃で3時間撹拌した。得られた混合物に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮し、次式で示される中間体1-2を0.22g得た。
3.72gの中間体1-2、N,N-ジメチルホルムアミドジメチルアセタール3.45g及びDMF15mLの混合物を、還流下で1日半撹拌した。得られた混合物に水を加え、MTBEで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮し、次式で示される中間体1-3を3.10g得た。
0.27gの中間体1-3及びメタノール10mLの混合物に、氷冷下で2N塩酸5mLを加え、室温で3時間撹拌した。得られた混合物に飽和食塩水を加え、酢酸エチルで抽出した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮し、次式で示される中間体1-4を0.23g得た。
0.23gの中間体1-4、炭酸セシウム0.34g及びNMP4mLの混合物に、ジメチル硫酸0.15gを加え、室温で3時間撹拌した。得られた混合物に飽和食塩水を加え、酢酸エチルで抽出した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体1-5を0.19g得た。
窒素雰囲気下で1.0gの中間体1-5、ビス(ピナコラト)ジボロン1.1g、PdCl2(dppf)0.24g、リン酸三カリウム0.66g、及びジメトキシエタン30mLの混合物を80℃で6時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体2-1を1.0g得た。
窒素雰囲気下で2.0gの中間体1-5、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド0.47g、トリブチル(1-エトキシビニル)スズ4.4mL及び1,4-ジオキサン20mLの混合物を、110℃で4時間撹拌した。得られた混合物に1N塩酸を加え、室温で1時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体3-1を1.4g得た。
0.54gの中間体2-1、メタクロロ過安息香酸0.50g、アセトニトリル5mL、エタノール5mL、及び水5mLの混合物を、室温で2.5時間撹拌した。得られた混合物にチオ硫酸ナトリウム水溶液、及び炭酸水素ナトリウム水溶液を加え、室温で2時間撹拌した。得られた混合物を酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体4-1を0.37g得た。
窒素雰囲気下で3-ブロモ-4,5-ジメチルフェノール2.0g、ビス(ピナコラト)ジボロン3.8g、PdCl2(dppf)0.36g、酢酸カリウム2.0g、及びDMSO25mLの混合物を80℃で7時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体5-1を2.6g得た。
参考製造例5に準じて製造した化合物及びその物性値を以下に示す。
式(C5-a):
中間体5-3:1H-NMR (CDCl3) δ: 7.31 (1H, s), 6.66 (1H, s), 5.29 (1H, s), 3.88 (3H, s), 2.48 (3H, s), 1.32 (12H, s).
窒素雰囲気下で、2.5gの中間体5-1、(Z)-2-ヨード-3-メトキシアクリル酸メチル2.9g、2-(ジシクロヘキシルホスフィノ)-2’,6’-ジメトキシビフェニル0.21g、0.23gのPd2(dba)3、リン酸三カリウム4.22g、トルエン25mL、及び水5mLの混合物を110℃で4時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体6-1を1.6g得た。
参考製造例6に準じて製造した化合物及びその物性値を以下に示す。
式(C6-a):
中間体6-3:1H-NMR (CDCl3) δ: 7.54 (1H, s), 6.72 (1H, s), 6.70 (1H, s), 5.40 (1H, s), 3.87 (3H, s), 3.83 (3H, s), 3.70 (3H, s), 2.11 (3H, s).
窒素雰囲気下、0.6gの中間体6-1及びクロロホルム6mLの混合物に、0℃でトリエチルアミン0.46mL及びトリフルオロ酢酸無水物0.50mLを順次加え、30分間撹拌した。得られた混合物に重曹水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮し、次式で示される中間体7-1を0.70g得た。
参考製造例7に準じて製造した化合物及びその物性値を以下に示す。
式(C7-a):
中間体7-3:1H-NMR (CDCl3) δ: 7.57 (1H, s), 6.97 (1H, s), 6.87 (1H, s), 3.90 (3H, s), 3.85 (3H, s), 3.71 (3H, s), 2.19 (3H, s).
窒素雰囲気下で、1,5-ジブロモ-2,4-ジメチルベンゼン5g及びTHF30mLの混合物に、-78℃でブチルリチウム(1.6Mヘキサン溶液)12mLを滴下した後、-78℃で1時間撹拌した。得られた混合物にシュウ酸ジメチル2.5gを加え、0℃で3時間撹拌した。得られた混合物に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体8-1を3.9g得た。
参考製造例8に準じて製造した化合物及びその物性値を以下に示す。
3.5gの中間体8-1、O-メチルヒドロキシルアミン塩酸塩2.3g及びエタノール80mLの混合物を、55℃で6時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体9-1を1.3g得た。
参考製造例9に準じて製造した化合物及びその物性値を以下に示す。
0.20gの中間体3-1、О-メチルヒドロキシルアミン塩酸塩0.13g及びエタノール5mLの混合物に、室温で、ピリジン0.10mLを加え、室温で終夜撹拌した。得られた混合物を酢酸エチルで希釈し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=3:7)に付し、次式で示される本発明化合物1-1を0.22g得た。
製造例1に準じて製造した化合物及びその物性値を以下に示す。
式(1-1):
本発明化合物1-3:1H-NMR (CDCl3) δ: 7.55 (1H, s), 7.06 (1H, s), 6.99 (1H, s), 3.96 (2H, d), 3.81 (3H, s), 3.68 (3H, s), 2.35 (3H, s), 2.19 (3H, s), 2.14 (3H, s), 1.25-1.15 (1H, m), 0.58-0.52 (2H, m), 0.33-0.28 (2H, m).
本発明化合物1-4:1H-NMR (CDCl3) δ: 7.58 (1H, s), 7.33-7.27 (2H, m), 7.25-7.21 (2H, m), 7.13 (1H, s), 7.09 (1H, s), 7.02-6.98 (1H, m), 3.83 (3H, s), 3.71 (3H, s), 2.43 (3H, s), 2.39 (3H, s), 2.18 (3H, s).
本発明化合物1-5:1H-NMR (CDCl3) δ: 7.55 (1H, s), 7.43-7.32 (5H, m), 7.04 (1H, s), 6.97 (1H, s), 5.19 (2H, s), 3.80 (3H, s), 3.68 (3H, s), 2.25 (3H, s), 2.20 (3H, s), 2.13 (3H, s).
本発明化合物1-6:1H-NMR (CDCl3) δ: 7.56 (1H, s), 7.07 (1H, s), 6.98 (1H, s), 4.74 (1H, t), 4.62 (1H, t), 4.41 (1H, t), 4.34 (1H, t), 3.82 (3H, s), 3.69 (3H, s), 2.34 (3H, s), 2.20 (3H, s), 2.14 (3H, s).
本発明化合物1-7:1H-NMR (CDCl3) δ: 8.29 (1H, s), 7.56 (1H, s), 7.44 (1H, s), 7.05 (1H, s), 4.21 (2H, q), 3.82 (3H, s), 3.69 (3H, s), 2.38 (3H, s), 2.15 (3H, s), 1.32 (3H, t).
本発明化合物1-8:1H-NMR (CDCl3) δ: 8.35 (1H, s), 7.56 (1H, s), 7.43-7.40 (2H, m), 7.38-7.30 (4H, m), 7.05 (1H, s), 5.19 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.36 (3H, s), 2.15 (3H, s).
本発明化合物1-9:1H-NMR (CDCl3) δ: 8.33 (1H, s), 7.56 (1H, s), 7.40 (1H, s), 7.37-7.30 (4H, m), 7.05 (1H, s), 5.14 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.36 (3H, s), 2.15 (3H, s).
窒素雰囲気下で0.10gの中間体1-5、0.02gのPdCl2(PPh3)2、シクロプロピルアセチレン0.15mL、テトラブチルアンモニウムフルオリド(1mol/LのTHF溶液)1.0mL、及びTHF3mLの混合物を、80℃で6時間撹拌した。得られた混合物に重曹水を加えて、酢酸エチルで抽出した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:3)に付し、次式で示される本発明化合物2-1を0.09g得た。
製造例2に準じて製造した化合物及びその物性値を以下に示す。
式(2-1):
本発明化合物2-3:LCMS: 301 [M+H]+, RT = 2.33 分
本発明化合物2-4:1H-NMR (CDCl3) δ: 7.62-7.51 (3H, m), 7.38-7.34 (3H, m), 6.98-6.92 (1H, m), 4.14 (3H, s), 3.91 (3H, s).
0.18gの中間体4-1、ブタノール0.06mL、ビス(2-メトキシエチル) アゾジカルボキシラート0.13g、トリフェニルホスフィン0.13g、及びクロロホルム4mLの混合物を、室温で4時間撹拌した。得られた混合物に、重曹水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:3)に付し、次式で示される本発明化合物3-1を0.13g得た。
製造例3に準じて製造した化合物及びその物性値を以下に示す。
式(3-1):
本発明化合物3-3:1H-NMR (CDCl3) δ: 7.55 (1H, s), 6.93 (1H, d), 6.70 (1H, d), 3.99 (2H, t), 3.84 (3H, s), 3.71 (3H, s), 2.08 (3H, s), 1.82-1.73 (2H, m), 1.53-1.43 (2H, m), 0.96 (3H, t).
本発明化合物3-4:1H-NMR (CDCl3) δ: 7.55 (1H, s), 6.73 (1H, s), 6.63 (1H, s), 3.97 (2H, t), 3.85 (3H, s), 3.84 (3H, s), 3.71 (3H, s), 2.12 (3H, s), 1.84-1.74 (2H, m), 1.52-1.41 (2H, m), 0.95 (3H, t).
窒素雰囲気下で0.20gの中間体7-2、3-メトキシフェニルボロン酸0.11g、PdCl2(dppf)0.02g、リン酸三カリウム0.23g、ジメトキシエタン4mL及び水0.4mLの混合物を80℃で3時間撹拌した。得られた混合物に、水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:3)に付し、次式で示される本発明化合物4-1を0.16g得た。
製造例4に準じて製造した化合物及びその物性値を以下に示す。
式(4-1):
本発明化合物4-3:1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.30 (1H, t), 7.14 (1H, s), 7.01 (1H, s), 6.95-6.92 (1H, m), 6.90-6.84 (2H, m), 3.83 (3H, s), 3.82 (3H, s), 3.71 (3H, s), 2.26 (3H, s), 2.20 (3H, s).
本発明化合物4-4:1H-NMR (CDCl3) δ: 7.58 (1H, s), 7.28-7.20 (4H, m), 7.10 (1H, s), 6.97 (1H, s), 3.82 (3H, s), 3.71 (3H, s), 2.34 (3H, s), 2.31 (3H, s), 2.13 (3H, s).
本発明化合物4-5:1H-NMR (CDCl3) δ: 7.60 (1H, s), 7.35 (1H, d), 7.32 (1H, t), 7.20 (1H, d), 7.19-7.15 (1H, m), 7.11 (1H, t), 6.87-6.83 (1H, m), 3.85 (3H, s), 3.83 (3H, s), 3.71 (3H, s), 2.36 (3H, s), 2.12 (3H, s).
本発明化合物4-6:1H-NMR (CDCl3) δ: 7.83 (1H, s), 7.81-7.77 (1H, m), 7.64-7.59 (2H, m), 7.52 (1H, t), 7.16 (1H, d), 7.06 (1H, d), 3.86 (3H, s), 3.73 (3H, s), 2.22 (3H, s).
本発明化合物4-7:1H-NMR (CDCl3) δ: 7.42-7.31 (5H, m), 7.17 (1H, s), 7.00 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.27 (3H, s), 2.20 (3H, s).
本発明化合物4-8:1H-NMR (CDCl3) δ: 7.35-7.29 (3H, m), 7.23-7.19 (1H, m), 7.17 (1H, s), 6.96 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.26 (3H, s), 2.20 (3H, s).
本発明化合物4-9:1H-NMR (CDCl3) δ: 7.34-7.28 (1H, m), 7.17 (1H, s), 7.00 (1H, s), 6.93-6.86 (3H, m), 4.07 (3H, s), 3.87 (3H, s), 3.82 (3H, s), 2.28 (3H, s), 2.20 (3H, s).
本発明化合物4-10:1H-NMR (CDCl3) δ: 7.45-7.39 (1H, m), 7.28-7.25 (1H, m), 7.21-7.17 (3H, m), 6.98 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.27 (3H, s), 2.21 (3H, s).
本発明化合物4-11:1H-NMR (CDCl3) δ: 7.61-7.57 (2H, m), 7.53-7.50 (2H, m), 7.21-7.19 (1H, m), 6.98 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.26 (3H, s), 2.21 (3H, s).
本発明化合物4-12:1H-NMR (CDCl3) δ: 7.41-7.28 (5H, m), 7.16 (1H, s), 6.99 (1H, s), 6.78 (1H, s), 3.97 (3H, s), 2.93 (3H, d), 2.26 (3H, s), 2.20 (3H, s).
本発明化合物4-13:1H-NMR (CDCl3) δ: 7.34-7.32 (1H, m), 7.31-7.27 (2H, m), 7.23-7.20 (1H, m), 7.15 (1H, s), 6.95 (1H, s), 6.79 (1H, br s), 3.98 (3H, s), 2.93 (3H, d), 2.25 (3H, s), 2.19 (3H, s).
本発明化合物4-14:LCMS: 311 [M+H]+, RT = 2.19 分
本発明化合物4-15:1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.31-7.25 (1H, m), 7.17-7.10 (4H, m), 7.00 (1H, s), 3.82 (3H, s), 3.71 (3H, s), 2.38 (3H, s), 2.26 (3H, s), 2.19 (3H, s).
本発明化合物4-16:LCMS: 311 [M+H]+, RT = 2.20 分
本発明化合物4-17:LCMS: 315 [M+H]+, RT = 2.09 分
本発明化合物4-18:1H-NMR (CDCl3) δ: 7.58 (1H, s), 7.37-7.31 (1H, m), 7.16-7.10 (2H, m), 7.08-6.97 (3H, m), 3.84 (3H, s), 3.71 (3H, s), 2.25 (3H, s), 2.20 (3H, s).
本発明化合物4-19:LCMS: 315 [M+H]+, RT = 2.12 分
本発明化合物4-20:LCMS: 327 [M+H]+, RT = 2.07 分
本発明化合物4-21:LCMS: 327 [M+H]+, RT = 2.08 分
本発明化合物4-22:LCMS: 331 [M+H]+, RT = 2.22 分
本発明化合物4-23:LCMS: 343 [M+H]+, RT = 2.18 分
本発明化合物4-24:1H-NMR (CDCl3) δ: 7.56 (1H, s), 7.37-7.31 (3H, m), 7.13-7.03 (5H, m), 7.00-6.94 (3H, m), 3.82 (3H, s), 3.70 (3H, s), 2.24 (3H, s), 2.18 (3H, s).
本発明化合物4-25:1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.47-7.27 (6H, m), 7.13 (1H, s), 7.00 (1H, s), 6.97-6.92 (3H, m), 5.08 (2H, s), 3.82 (3H, s), 3.71 (3H, s), 2.21 (3H, s), 2.19 (3H, s).
本発明化合物4-26:LCMS: 342 [M+H]+, RT = 2.11 分
本発明化合物4-27:LCMS: 337 [M+H]+, RT = 2.31 分
本発明化合物4-28:LCMS: 345 [M+H]+, RT = 2.04 分
本発明化合物4-29:LCMS: 333 [M+H]+, RT = 2.16 分
本発明化合物4-30:LCMS: 324 [M+H]+, RT = 2.04 分
窒素雰囲気下で0.18gの中間体2-1、2-ブロモ-3-フルオロピリジン0.09mL、PdCl2(dppf)0.02g、リン酸三カリウム0.24g、ジメトキシエタン4mL及び水1mLの混合物を80℃で8時間撹拌した。得られた混合物に、水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=2:3)に付し、次式で示される本発明化合物5-1を0.10g得た。
製造例5に準じて製造した化合物及びその物性値を以下に示す。
式(5-1):
本発明化合物5-3:1H-NMR (CDCl3) δ: 7.18 (1H, s), 7.13 (1H, d), 7.01 (1H, s), 6.90 (1H, d), 4.07 (3H, s), 3.87 (3H, s), 2.22 (3H, s), 2.20 (3H, s).
本発明化合物5-4:1H-NMR (CDCl3) δ: 7.18 (1H, s), 7.13 (1H, d), 7.01 (1H, s), 6.90 (1H, d), 4.07 (3H, s), 3.87 (3H, s), 2.22 (3H, s), 2.20 (3H, s).
本発明化合物5-5:1H-NMR (CDCl3) δ: 7.87 (1H, s), 7.84 (1H, s), 7.58 (1H, s), 7.16 (1H, s), 7.07 (1H, s), 3.84 (3H, s), 3.72 (3H, s), 2.35 (3H, s), 2.18 (3H, s).
窒素雰囲気下で0.10gの中間体1-5、1-シクロペンテニルボロン酸0.08g、PdCl2(dppf)0.02g、リン酸三カリウム0.21g、ジメトキシエタン4mL及び水1mLの混合物を80℃で6時間撹拌した。得られた混合物に、水を加え、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:3)に付し、次式で示される本発明化合物6-1を0.08g得た。
[ZA1;Me,H],[ZA2;Et,H],[ZA3;Pr,H],[ZA4;Bu,H],[ZA5;Pen,H],[ZA6;Hex,H],[ZA7;i-Pr,H],[ZA8;i-Bu,H],[ZA9;t-Bu,H],[ZA10;c-Pr,H],[ZA11;c-Bu,H],[ZA12;c-Pen,H],[ZA13;c-Hex,H],[ZA14;CH2c-Pr,H],[ZA15;CH2c-Pen,H],[ZA16;CH2c-Hex,H],[ZA17;CH2CH=CH2,H],[ZA18;CH2CH=CHMe,H],[ZA19;CH2CH=CMe2,H],[ZA20;CH2C≡CH,H],[ZA21;CH2C≡CMe,H],[ZA22;CH2Ph,H],[ZA23;CH2(2-F-Ph),H],[ZA24;CH2(3-F-Ph),H],[ZA25;CH2(4-F-Ph),H],[ZA26;CH2(2-Cl-Ph),H],[ZA27;CH2(3-Cl-Ph),H],[ZA28;CH2(4-Cl-Ph),H],[ZA29;CH2(2-Br-Ph),H],[ZA30;CH2(3-Br-Ph),H],[ZA31;CH2(4-Br-Ph),H],[ZA32;CH2(2-Me-Ph),H],[ZA33;CH2(3-Me-Ph),H],[ZA34;CH2(4-Me-Ph),H],[ZA35;CH2(2-Et-Ph),H],[ZA36;CH2(3-Et-Ph),H],[ZA37;CH2(4-Et-Ph),H],[ZA38;CH2(2-t-Bu-Ph),H],[ZA39;CH2(3-t-Bu-Ph),H],[ZA40;CH2(4-t-Bu-Ph),H],[ZA41;CH2(2-CF3-Ph),H],[ZA42;CH2(3-CF3-Ph),H],[ZA43;CH2(4-CF3-Ph),H],[ZA44;CH2(2-OMe-Ph),H],[ZA45;CH2(3-OMe-Ph),H],[ZA46;CH2(4-OMe-Ph),H],[ZA47;CH2(2-SMe-Ph),H],[ZA48;CH2(3-SMe-Ph),H],[ZA49;CH2(4-SMe-Ph),H],[ZA50;CH2(2-CN-Ph),H],[ZA51;CH2(3-CN-Ph),H],[ZA52;CH2(4-CN-Ph),H],[ZA53;CH2(2,4-F2-Ph),H],[ZA54;CH2(2,5-F2-Ph),H],[ZA55;CH2(3,4-F2-Ph),H],[ZA56;CH2(3,5-F2-Ph),H],[ZA57;CH2(2,4-Cl2-Ph),H],[ZA58;CH2(2,5-Cl2-Ph),H],[ZA59;CH2(3,4-Cl2-Ph),H],[ZA60;CH2(3,5-Cl2-Ph),H],[ZA61;CH2(2,4-Me2-Ph),H],[ZA62;CH2(2,5-Me2-Ph),H],[ZA63;CH2(3,4-Me2-Ph),H],[ZA64;CH2(3,5-Me2-Ph),H],[ZA65;CH2(2-F-4-Cl-Ph),H],[ZA66;CH2(2-Cl-4-F-Ph),H],[ZA67;CH2(2-F-4-Me-Ph),H],[ZA68;CH2(2-Me-4-F-Ph),H],[ZA69;CH2(2-F-4-OMe-Ph),H],[ZA70;CH2(2-OMe-4-F-Ph),H],[ZA71;CH2(2-Me-4-Cl-Ph),H],[ZA72;CH2(2-Cl-4-Me-Ph),H],[ZA73;CH2(2-Me-4-OMe-Ph),H],[ZA74;CH2(2-OMe-4-Me-Ph),H],[ZA75;CH2(2-Cl-4-OMe-Ph),H],[ZA76;CH2(2-OMe-4-Cl-Ph),H],[ZA77;CH2(2,4,6-F3-Ph),H],[ZA78;CH2(3,4,5-F3-Ph),H],[ZA79;CH2(2-pyridyl),H],[ZA80;CH2(3-pyridyl),H],[ZA81;CH2(4-pyridyl),H],[ZA82;CH2(3-F-pyridin-2-yl),H],[ZA83;CH2(4-F-pyridin-2-yl),H],[ZA84;CH2(5-F-pyridin-2-yl),H],[ZA85;CH2(6-F-pyridin-2-yl),H],[ZA86;CH2(3-Cl-pyridin-2-yl),H],[ZA87;CH2(4-Cl-pyridin-2-yl),H],[ZA88;CH2(5-Cl-pyridin-2-yl),H],[ZA89;CH2(6-Cl-pyridin-2-yl),H],[ZA90;CH2(3-Me-pyridin-2-yl),H],[ZA91;CH2(4-Me-pyridin-2-yl),H],[ZA92;CH2(5-Me-pyridin-2-yl),H],[ZA93;CH2(6-Me-pyridin-2-yl),H],[ZA94;CH2(3-OMe-pyridin-2-yl),H],[ZA95;CH2(4-OMe-pyridin-2-yl),H],[ZA96;CH2(5-OMe-pyridin-2-yl),H],[ZA97;CH2(6-OMe-pyridin-2-yl),H],[ZA98;CH2(3-CF3-pyridin-2-yl),H],[ZA99;CH2(4-CF3-pyridin-2-yl),H],[ZA100;CH2(5-CF3-pyridin-2-yl),H],[ZA101;CH2(6-CF3-pyridin-2-yl),H],[ZA102;CH2(3-CN-pyridin-2-yl),H],[ZA103;CH2(4-CN-pyridin-2-yl),H],[ZA104;CH2(5-CN-pyridin-2-yl),H],[ZA105;CH2(6-CN-pyridin-2-yl),H],[ZA106;CH2(2-F-pyridin-3-yl),H],[ZA107;CH2(4-F-pyridin-3-yl),H],[ZA108;CH2(5-F-pyridin-3-yl),H],[ZA109;CH2(6-F-pyridin-3-yl),H],[ZA110;CH2(2-Cl-pyridin-3-yl),H],[ZA111;CH2(4-Cl-pyridin-3-yl),H],[ZA112;CH2(5-Cl-pyridin-3-yl),H],[ZA113;CH2(6-Cl-pyridin-3-yl),H],[ZA114;CH2(2-Me-pyridin-3-yl),H],[ZA115;CH2(4-Me-pyridin-3-yl),H],[ZA116;CH2(5-Me-pyridin-3-yl),H],[ZA117;CH2(6-Me-pyridin-3-yl),H],[ZA118;CH2(2-OMe-pyridin-3-yl),H],[ZA119;CH2(4-OMe-pyridin-3-yl),H],[ZA120;CH2(5-OMe-pyridin-3-yl),H],[ZA121;CH2(6-OMe-pyridin-3-yl),H],[ZA122;CH2(2-CF3-pyridin-3-yl),H],[ZA123;CH2(4-CF3-pyridin-3-yl),H],[ZA124;CH2(5-CF3-pyridin-3-yl),H],[ZA125;CH2(6-CF3-pyridin-3-yl),H],[ZA126;CH2(2-CN-pyridin-3-yl),H],[ZA127;CH2(4-CN-pyridin-3-yl),H],[ZA128;CH2(5-CN-pyridin-3-yl),H],[ZA129;CH2(6-CN-pyridin-3-yl),H],[ZA130;CH2(2-F-pyridin-4-yl),H],[ZA131;CH2(3-F-pyridin-4-yl),H],[ZA132;CH2(2-Cl-pyridin-4-yl),H],[ZA133;CH2(3-Cl-pyridin-4-yl),H],[ZA134;CH2(2-Me-pyridin-4-yl),H],[ZA135;CH2(3-Me-pyridin-4-yl),H],[ZA136;CH2(2-OMe-pyridin-4-yl),H],[ZA137;CH2(3-OMe-pyridin-4-yl),H],[ZA138;CH2(2-CF3-pyridin-4-yl),H],[ZA139;CH2(3-CF3-pyridin-4-yl),H],[ZA140;CH2(2-CN-pyridin-4-yl),H],[ZA141;CH2(3-CN-pyridin-4-yl),H],[ZA142;CH2(2-Thienyl),H],[ZA143;CH2(3-Thienyl),H],[ZA144;CH2(2-pyrimidinyl),H],[ZA145;CH2(4-pyrimidinyl),H],[ZA146;CH2(5-pyrimidinyl),H],[ZA147;CH2(3-pyridazinyl),H],[ZA148;CH2(4-pyridazinyl),H],[ZA149;CH2(4-Me-thiazol-2-yl),H],[ZA150;CH2(4-Cl-thiazol-2-yl),H],[ZA151;CH2(5-Me-thiazol-2-yl),H],[ZA152;CH2(5-Cl-thiazol-2-yl),H],[ZA153;(CH22Ph,H],[ZA154;(CH23Ph,H],[ZA155;CH2OMe,H],[ZA156;CH2OEt,H],[ZA157;CH2OPr,H],[ZA158;CH2OPh,H],[ZA159;CH2CN,H],[ZA160;Ph,H],[ZA161;2-F-Ph,H],[ZA162;3-F-Ph,H],[ZA163;4-F-Ph,H],[ZA164;2-Cl-Ph,H],[ZA165;3-Cl-Ph,H],[ZA166;4-Cl-Ph,H],[ZA167;2-Me-Ph,H],[ZA168;3-Me-Ph,H],[ZA169;4-Me-Ph,H],[ZA170;2-OMe-Ph,H],[ZA171;3-OMe-Ph,H],[ZA172;4-OMe-Ph,H],[ZA173;2-Pyridyl,H],[ZA174;3-Pyridyl,H],[ZA175;4-Pyridyl,H],[ZA176;2-Thienyl,H],[ZA177;3-Thienyl,H],[ZA178;2-pyrimidinyl,H],[ZA179;4-pyrimidinyl,H],[ZA180;5-pyrimidinyl,H],[ZA181;3-pyridazinyl,H],[ZA182;4-pyridazinyl,H],[ZA183;Me,Me],[ZA184;Et,Me],[ZA185;Pr,Me],[ZA186;Bu,Me],[ZA187;Pen,Me],[ZA188;Hex,Me],[ZA189;i-Pr,Me],[ZA190;i-Bu,Me],[ZA191;t-Bu,Me],[ZA192;c-Pr,Me],[ZA193;c-Bu,Me],[ZA194;c-Pen,Me],[ZA195;c-Hex,Me],[ZA196;CH2c-Pr,Me],[ZA197;CH2c-Pen,Me],[ZA198;CH2c-Hex,Me],[ZA199;CH2CH=CH2,Me],[ZA200;CH2CH=CHMe,Me],
[ZA201;CH2CH=CMe2,Me],[ZA202;CH2C≡CH,Me],[ZA203;CH2C≡CMe,Me],[ZA204;CH2Ph,Me],[ZA205;CH2(2-F-Ph),Me],[ZA206;CH2(3-F-Ph),Me],[ZA207;CH2(4-F-Ph),Me],[ZA208;CH2(2-Cl-Ph),Me],[ZA209;CH2(3-Cl-Ph),Me],[ZA210;CH2(4-Cl-Ph),Me],[ZA211;CH2(2-Br-Ph),Me],[ZA212;CH2(3-Br-Ph),Me],[ZA213;CH2(4-Br-Ph),Me],[ZA214;CH2(2-Me-Ph),Me],[ZA215;CH2(3-Me-Ph),Me],[ZA216;CH2(4-Me-Ph),Me],[ZA217;CH2(2-Et-Ph),Me],[ZA218;CH2(3-Et-Ph),Me],[ZA219;CH2(4-Et-Ph),Me],[ZA220;CH2(2-t-Bu-Ph),Me],[ZA221;CH2(3-t-Bu-Ph),Me],[ZA222;CH2(4-t-Bu-Ph),Me],[ZA223;CH2(2-CF3-Ph),Me],[ZA224;CH2(3-CF3-Ph),Me],[ZA225;CH2(4-CF3-Ph),Me],[ZA226;CH2(2-OMe-Ph),Me],[ZA227;CH2(3-OMe-Ph),Me],[ZA228;CH2(4-OMe-Ph),Me],[ZA229;CH2(2-SMe-Ph),Me],[ZA230;CH2(3-SMe-Ph),Me],[ZA231;CH2(4-SMe-Ph),Me],[ZA232;CH2(2-CN-Ph),Me],[ZA233;CH2(3-CN-Ph),Me],[ZA234;CH2(4-CN-Ph),Me],[ZA235;CH2(2,4-F2-Ph),Me],[ZA236;CH2(2,5-F2-Ph),Me],[ZA237;CH2(3,4-F2-Ph),Me],[ZA238;CH2(3,5-F2-Ph),Me],[ZA239;CH2(2,4-Cl2-Ph),Me],[ZA240;CH2(2,5-Cl2-Ph),Me],[ZA241;CH2(3,4-Cl2-Ph),Me],[ZA242;CH2(3,5-Cl2-Ph),Me],[ZA243;CH2(2,4-Me2-Ph),Me],[ZA244;CH2(2,5-Me2-Ph),Me],[ZA245;CH2(3,4-Me2-Ph),Me],[ZA246;CH2(3,5-Me2-Ph),Me],[ZA247;CH2(2-F-4-Cl-Ph),Me],[ZA248;CH2(2-Cl-4-F-Ph),Me],[ZA249;CH2(2-F-4-Me-Ph),Me],[ZA250;CH2(2-Me-4-F-Ph),Me],[ZA251;CH2(2-F-4-OMe-Ph),Me],[ZA252;CH2(2-OMe-4-F-Ph),Me],[ZA253;CH2(2-Me-4-Cl-Ph),Me],[ZA254;CH2(2-Cl-4-Me-Ph),Me],[ZA255;CH2(2-Me-4-OMe-Ph),Me],[ZA256;CH2(2-OMe-4-Me-Ph),Me],[ZA257;CH2(2-Cl-4-OMe-Ph),Me],[ZA258;CH2(2-OMe-4-Cl-Ph),Me],[ZA259;CH2(2,4,6-F3-Ph),Me],[ZA260;CH2(3,4,5-F3-Ph),Me],[ZA261;CH2(2-pyridyl),Me],[ZA262;CH2(3-pyridyl),Me],[ZA263;CH2(4-pyridyl),Me],[ZA264;CH2(3-F-pyridin-2-yl),Me],[ZA265;CH2(4-F-pyridin-2-yl),Me],[ZA266;CH2(5-F-pyridin-2-yl),Me],[ZA267;CH2(6-F-pyridin-2-yl),Me],[ZA268;CH2(3-Cl-pyridin-2-yl),Me],[ZA269;CH2(4-Cl-pyridin-2-yl),Me],[ZA270;CH2(5-Cl-pyridin-2-yl),Me],[ZA271;CH2(6-Cl-pyridin-2-yl),Me],[ZA272;CH2(3-Me-pyridin-2-yl),Me],[ZA273;CH2(4-Me-pyridin-2-yl),Me],[ZA274;CH2(5-Me-pyridin-2-yl),Me],[ZA275;CH2(6-Me-pyridin-2-yl),Me],[ZA276;CH2(3-OMe-pyridin-2-yl),Me],[ZA277;CH2(4-OMe-pyridin-2-yl),Me],[ZA278;CH2(5-OMe-pyridin-2-yl),Me],[ZA279;CH2(6-OMe-pyridin-2-yl),Me],[ZA280;CH2(3-CF3-pyridin-2-yl),Me],[ZA281;CH2(4-CF3-pyridin-2-yl),Me],[ZA282;CH2(5-CF3-pyridin-2-yl),Me],[ZA283;CH2(6-CF3-pyridin-2-yl),Me],[ZA284;CH2(3-CN-pyridin-2-yl),Me],[ZA285;CH2(4-CN-pyridin-2-yl),Me],[ZA286;CH2(5-CN-pyridin-2-yl),Me],[ZA287;CH2(6-CN-pyridin-2-yl),Me],[ZA288;CH2(2-F-pyridin-3-yl),Me],[ZA289;CH2(4-F-pyridin-3-yl),Me],[ZA290;CH2(5-F-pyridin-3-yl),Me],[ZA291;CH2(6-F-pyridin-3-yl),Me],[ZA292;CH2(2-Cl-pyridin-3-yl),Me],[ZA293;CH2(4-Cl-pyridin-3-yl),Me],[ZA294;CH2(5-Cl-pyridin-3-yl),Me],[ZA295;CH2(6-Cl-pyridin-3-yl),Me],[ZA296;CH2(2-Me-pyridin-3-yl),Me],[ZA297;CH2(4-Me-pyridin-3-yl),Me],[ZA298;CH2(5-Me-pyridin-3-yl),Me],[ZA299;CH2(6-Me-pyridin-3-yl),Me],[ZA300;CH2(2-OMe-pyridin-3-yl),Me],[ZA301;CH2(4-OMe-pyridin-3-yl),Me],[ZA302;CH2(5-OMe-pyridin-3-yl),Me],[ZA303;CH2(6-OMe-pyridin-3-yl),Me],[ZA304;CH2(2-CF3-pyridin-3-yl),Me],[ZA305;CH2(4-CF3-pyridin-3-yl),Me],[ZA306;CH2(5-CF3-pyridin-3-yl),Me],[ZA307;CH2(6-CF3-pyridin-3-yl),Me],[ZA308;CH2(2-CN-pyridin-3-yl),Me],[ZA309;CH2(4-CN-pyridin-3-yl),Me],[ZA310;CH2(5-CN-pyridin-3-yl),Me],[ZA311;CH2(6-CN-pyridin-3-yl),Me],[ZA312;CH2(2-F-pyridin-4-yl),Me],[ZA313;CH2(3-F-pyridin-4-yl),Me],[ZA314;CH2(2-Cl-pyridin-4-yl),Me],[ZA315;CH2(3-Cl-pyridin-4-yl),Me],[ZA316;CH2(2-Me-pyridin-4-yl),Me],[ZA317;CH2(3-Me-pyridin-4-yl),Me],[ZA318;CH2(2-OMe-pyridin-4-yl),Me],[ZA319;CH2(3-OMe-pyridin-4-yl),Me],[ZA320;CH2(2-CF3-pyridin-4-yl),Me],[ZA321;CH2(3-CF3-pyridin-4-yl),Me],[ZA322;CH2(2-CN-pyridin-4-yl),Me],[ZA323;CH2(3-CN-pyridin-4-yl),Me],[ZA324;CH2(2-Thienyl),Me],[ZA325;CH2(3-Thienyl),Me],[ZA326;CH2(2-pyrimidinyl),Me],[ZA327;CH2(4-pyrimidinyl),Me],[ZA328;CH2(5-pyrimidinyl),Me],[ZA329;CH2(3-pyridazinyl),Me],[ZA330;CH2(4-pyridazinyl),Me],[ZA331;CH2(4-Me-thiazol-2-yl),Me],[ZA332;CH2(4-Cl-thiazol-2-yl),Me],[ZA333;CH2(5-Me-thiazol-2-yl),Me],[ZA334;CH2(5-Cl-thiazol-2-yl),Me],[ZA335;(CH22Ph,Me],[ZA336;(CH23Ph,Me],[ZA337;CH2OMe,Me],[ZA338;CH2OEt,Me],[ZA339;CH2OPr,Me],[ZA340;CH2OPh,Me],[ZA341;CH2CN,Me],[ZA342;Ph,Me],[ZA343;2-F-Ph,Me],[ZA344;3-F-Ph,Me],[ZA345;4-F-Ph,Me],[ZA346;2-Cl-Ph,Me],[ZA347;3-Cl-Ph,Me],[ZA348;4-Cl-Ph,Me],[ZA349;2-Me-Ph,Me],[ZA350;3-Me-Ph,Me],[ZA351;4-Me-Ph,Me],[ZA352;2-OMe-Ph,Me],[ZA353;3-OMe-Ph,Me],[ZA354;4-OMe-Ph,Me],[ZA355;2-Pyridyl,Me],[ZA356;3-Pyridyl,Me],[ZA357;4-Pyridyl,Me],[ZA358;2-Thienyl,Me],[ZA359;3-Thienyl,Me],[ZA360;2-pyrimidinyl,Me],[ZA361;4-pyrimidinyl,Me],[ZA362;5-pyrimidinyl,Me],[ZA363;3-pyridazinyl,Me],[ZA364;4-pyridazinyl,Me]
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX3と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX4と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX5と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX6と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子あり、RX22がメチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX7と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX8と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX9と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX10と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX11と記す)。
化合物(1A)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX12と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX13と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がエチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX14と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX15と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX16と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX17と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX18と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX19と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX20と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX21と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX22と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX23と記す)。
化合物(1A)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX24と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX25と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がエチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX26と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX27と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX28と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメトキシ基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX29と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がシクロプロピル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX30と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子あり、RX2がメチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX31と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX32と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX33と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1が塩素原子あり、RX2がメチル基であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX34と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2がフッ素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX35と記す)。
化合物(1A)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2が塩素原子であり、R3、及びR4が組合せAに記載のいずれかの組合せである化合物(以下、化合物群SX36と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX39と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX40と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX41と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX42と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX43と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX44と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX45と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX46と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX47と記す)。
化合物(1B)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX48と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX49と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がエチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX50と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX51と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX52と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX53と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX54と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX55と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX56と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX57と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX58と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX59と記す)。
化合物(1B)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX60と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX61と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がエチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX62と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX63と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX64と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメトキシ基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX65と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がシクロプロピル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX66と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子あり、RX2がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX67と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX68と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX69と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1が塩素原子あり、RX2がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX70と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX71と記す)。
化合物(1B)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX72と記す)。
化合物(2B)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX74と記す)。
化合物(2B)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX75と記す)。
化合物(2B)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28がメトキシ基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX76と記す)。
化合物(2B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX77と記す)。
化合物(2B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX78と記す)。
化合物(2B)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX79と記す)。
化合物(2B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28がメチル基であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX80と記す)。
化合物(2B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28がフッ素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX81と記す)。
化合物(2B)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28が塩素原子であり、R5が群Vから選ばれるいずれかの置換基である化合物(以下、化合物群SX82と記す)。
CH2CH=NOCH3,CH2CH=NOCH2CH3,CH2CH=NOCH2Ph,CH2C(CH3)=NOCH3,CH2C(CH3)=NOCH2CH3,CH2C(CH3)=NOCH2Ph,(CH2)2F,CH2CF3,(CH2)2Cl,CH2CCl3,(CH2)2Br,(CH2)2I,(CH2)2CF3,(CH2)2CN,(CH2)2NO2,(CH2)2OCH3,(CH2)2OCH2CH3,(CH2)2SCH3,(CH2)2SCH2CH3,(CH2)2SPh,(CH2)2NHCH3,(CH2)2N(CH3)2,(CH2)2NHPh,(CH2)2NHCH2Ph,(CH2)2N(CH3)CH2Ph,(CH2)2C(O)CH3,(CH2)2C(O)CH2CH3,(CH2)2C(O)Ph,(CH2)2C(O)NH2,(CH2)2C(O)NHCH3,(CH2)2C(O)N(CH3)2,(CH2)2C(O)NHPh,(CH2)2C(O)N(CH3)Ph,(CH2)2C(O)OCH3,(CH2)2C(O)OCH2CH3,(CH2)2NHC(O)CH3,(CH2)2NHC(O)CH2CH3,(CH2)2NHC(O)Ph,(CH2)2NCH3C(O)CH3,(CH2)2NCH3C(O)CH2CH3,(CH2)2NCH3C(O)Ph,(CH2)2NHC(O)OCH3,(CH2)2NHC(O)OCH2CH3,(CH2)2NHC(O)OPh,(CH2)2NCH3C(O)OCH3,(CH2)2NCH3C(O)OCH2CH3,(CH2)2NCH3C(O)OPh,(CH2)2NHC(O)NHCH3,(CH2)2NHC(O)NHCH2CH3,(CH2)2NHC(O)NHPh,(CH2)2NHC(O)N(CH3)2,(CH2)2NHC(O)N(CH3)CH2CH3,(CH2)2NHC(O)N(CH3)Ph,(CH2)2NHC(O)N(CH2CH3)2,(CH2)2NCH3C(O)NHCH3,(CH2)2NCH3C(O)NHCH2CH3,(CH2)2NCH3C(O)NHPh,(CH2)2NCH3C(O)N(CH3)2,(CH2)2NCH3C(O)N(CH3)CH2CH3,(CH2)2NCH3C(O)N(CH3)Ph,(CH2)2NCH3C(O)N(CH2CH3)2,(CH2)2OC(O)CH3,(CH2)2OC(O)CH2CH3,(CH2)2OC(O)Ph,(CH2)2OC(O)OCH3,(CH2)2OC(O)OCH2CH3,(CH2)2OC(O)OPh,(CH2)2OC(O)NHCH3,(CH2)2OC(O)NHCH2CH3,(CH2)2OC(O)NHPh,(CH2)2OC(O)N(CH3)2,(CH2)2OC(O)N(CH3)CH2CH3,(CH2)2OC(O)N(CH3)Ph,(CH2)2OC(O)N(CH2CH3)2,(CH2)3F,(CH2)3Cl,(CH2)3Br,(CH2)3I,(CH2)3CF3,(CH2)3CN,(CH2)3NO2,(CH2)3OCH3,(CH2)3OCH2CH3,(CH2)3SCH3,(CH2)3SCH2CH3,(CH2)3NHCH3,(CH2)3N(CH3)2,(CH2)4F,(CH2)4Cl,(CH2)4CF3,(CH2)4CN,(CH2)4NO2,(CH2)4Ph,(CH2)4OCH3,(CH2)4SCH3,(CH2)4NHCH3,(CH2)4N(CH3)2,(CH2)5F,(CH2)5Cl,(CH2)5CF3,(CH2)5CN,(CH2)5NO2,(CH2)5Ph,(CH2)5OCH3,(CH2)5SCH3,(CH2)5NHCH3,(CH2)5N(CH3)2,(CH2)6F,(CH2)6Cl,(CH2)6CF3,(CH2)6CN,(CH2)6NO2,(CH2)6Ph,(CH2)6OCH3,(CH2)6SCH3,(CH2)6NHCH3,(CH2)6N(CH3)2,CH2CF2CF3,(CH2)2CF2CF3,CH2(CF2)2CF3,(CH2)2CF(CF3)2,(CH2)2(CF2)5CF3,CF3,CHF2,CH2Fらなる群。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX85と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX86と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX87と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX88と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX89と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX90と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX91と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX92と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX93と記す)。
化合物(1C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX94と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX95と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がエチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX96と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX97と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX98と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX99と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX100と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX101と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX102と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX103と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX104と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX105と記す)。
化合物(1C)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX106と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX107と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がエチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX108と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX109と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX110と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメトキシ基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX111と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がシクロプロピル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX112と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子あり、RX2がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX113と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX114と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX115と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1が塩素原子あり、RX2がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX116と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX117と記す)。
化合物(1C)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX118と記す)。
[ZB1;H,H,H,H,H],[ZB2;Me,H,H,H,H],[ZB3;F,H,H,H,H],[ZB4;Cl,H,H,H,H],[ZB5;OMe,H,H,H,H],[ZB6;CF3,H,H,H,H],[ZB7;H,Me,H,H,H],[ZB8;H,Et,H,H,H],[ZB9;H,Pr,H,H,H],[ZB10;H,i-Pr,H,H,H],[ZB11;H,t-Bu,H,H,H],[ZB12;H,OMe,H,H,H],[ZB13;H,OEt,H,H,H],[ZB14;H,OPr,H,H,H],[ZB15;H,Oi-Pr,H,H,H],[ZB16;H,CF3,H,H,H],[ZB17;H,CF2H,H,H,H],[ZB18;H,CFH2,H,H,H],[ZB19;H,F,H,H,H],[ZB20;H,Cl,H,H,H],[ZB21;H,Br,H,H,H],[ZB22;H,CN,H,H,H],[ZB23;H,Ph,H,H,H],[ZB24;H,OPh,H,H,H],[ZB25;H,c-Pr,H,H,H],[ZB26;H,c-Pen,H,H,H],[ZB27;H,c-Hex,H,H,H],[ZB28;H,H,Me,H,H],[ZB29;H,H,Et,H,H],[ZB30;H,H,Pr,H,H],[ZB31;H,H,i-Pr,H,H],[ZB32;H,H,t-Bu,H,H],[ZB33;H,H,OMe,H,H],[ZB34;H,H,OEt,H,H],[ZB35;H,H,OPr,H,H],[ZB36;H,H,Oi-Pr,H,H],[ZB37;H,H,CF3,H,H],[ZB38;H,H,CF2H,H,H],[ZB39;H,H,CFH2,H,H],[ZB40;H,H,F,H,H],[ZB41;H,H,Cl,H,H],[ZB42;H,H,Br,H,H],[ZB43;H,H,CN,H,H],[ZB44;H,H,Ph,H,H],[ZB45;H,H,OPh,H,H],[ZB46;H,H,c-Pr,H,H],[ZB47;H,H,c-Pen,H,H],[ZB48;H,H,c-Hex,H,H],[ZB49;Me,H,H,H,F],[ZB50;F,H,H,H,F],[ZB51;Cl,H,H,H,F],[ZB52;H,Me,H,H,F],[ZB53;H,Et,H,H,F],[ZB54;H,Pr,H,H,F],[ZB55;H,i-Pr,H,H,F],[ZB56;H,t-Bu,H,H,F],[ZB57;H,OMe,H,H,F],[ZB58;H,OEt,H,H,F],[ZB59;H,OPr,H,H,F],[ZB60;H,Oi-Pr,H,H,F],[ZB61;H,CF3,H,H,F],[ZB62;H,CF2H,H,H,F],[ZB63;H,CFH2,H,H,F],[ZB64;H,F,H,H,F],[ZB65;H,Cl,H,H,F],[ZB66;H,Br,H,H,F],[ZB67;H,CN,H,H,F],[ZB68;H,Ph,H,H,F],[ZB69;H,OPh,H,H,F],[ZB70;H,c-Pr,H,H,F],[ZB71;H,c-Pen,H,H,F],[ZB72;H,c-Hex,H,H,F],[ZB73;H,H,Me,H,F],[ZB74;H,H,Et,H,F],[ZB75;H,H,Pr,H,F],[ZB76;H,H,i-Pr,H,F],[ZB77;H,H,t-Bu,H,F],[ZB78;H,H,OMe,H,F],[ZB79;H,H,OEt,H,F],[ZB80;H,H,OPr,H,F],[ZB81;H,H,Oi-Pr,H,F],[ZB82;H,H,CF3,H,F],[ZB83;H,H,CF2H,H,F],[ZB84;H,H,CFH2,H,F],[ZB85;H,H,F,H,F],[ZB86;H,H,Cl,H,F],[ZB87;H,H,Br,H,F],[ZB88;H,H,CN,H,F],[ZB89;H,H,Ph,H,F],[ZB90;H,H,OPh,H,F],[ZB91;H,H,c-Pr,H,F],[ZB92;H,H,c-Pen,H,F],[ZB93;H,H,c-Hex,H,F],[ZB94;Me,H,H,H,Cl],[ZB95;F,H,H,H,Cl],[ZB96;Cl,H,H,H,Cl],[ZB97;H,Me,H,H,Cl],[ZB98;H,Et,H,H,Cl],[ZB99;H,Pr,H,H,Cl],[ZB100;H,i-Pr,H,H,Cl],[ZB101;H,t-Bu,H,H,Cl],[ZB102;H,OMe,H,H,Cl],[ZB103;H,OEt,H,H,Cl],[ZB104;H,OPr,H,H,Cl],[ZB105;H,Oi-Pr,H,H,Cl],[ZB106;H,CF3,H,H,Cl],[ZB107;H,CF2H,H,H,Cl],[ZB108;H,CFH2,H,H,Cl],[ZB109;H,F,H,H,Cl],[ZB110;H,Cl,H,H,Cl],[ZB111;H,Br,H,H,Cl],[ZB112;H,CN,H,H,Cl],[ZB113;H,Ph,H,H,Cl],[ZB114;H,OPh,H,H,Cl],[ZB115;H,c-Pr,H,H,Cl],[ZB116;H,c-Pen,H,H,Cl],[ZB117;H,c-Hex,H,H,Cl],[ZB118;H,H,Me,H,Cl],[ZB119;H,H,Et,H,Cl],[ZB120;H,H,Pr,H,Cl],[ZB121;H,H,i-Pr,H,Cl],[ZB122;H,H,t-Bu,H,Cl],[ZB123;H,H,OMe,H,Cl],[ZB124;H,H,OEt,H,Cl],[ZB125;H,H,OPr,H,Cl],[ZB126;H,H,Oi-Pr,H,Cl],[ZB127;H,H,CF3,H,Cl],[ZB128;H,H,CF2H,H,Cl],[ZB129;H,H,CFH2,H,Cl],[ZB130;H,H,F,H,Cl],[ZB131;H,H,Cl,H,Cl],[ZB132;H,H,Br,H,Cl],[ZB133;H,H,CN,H,Cl],[ZB134;H,H,Ph,H,Cl],[ZB135;H,H,OPh,H,Cl],[ZB136;H,H,c-Pr,H,Cl],[ZB137;H,H,c-Pen,H,Cl],[ZB138;H,H,c-Hex,H,Cl],[ZB139;Me,H,H,H,Me],[ZB140;F,H,H,H,Me],[ZB141;Cl,H,H,H,Me],[ZB142;H,Me,H,H,Me],[ZB143;H,Et,H,H,Me],[ZB144;H,Pr,H,H,Me],[ZB145;H,i-Pr,H,H,Me],[ZB146;H,t-Bu,H,H,Me],[ZB147;H,OMe,H,H,Me],[ZB148;H,OEt,H,H,Me],[ZB149;H,OPr,H,H,Me],[ZB150;H,Oi-Pr,H,H,Me],
[ZB151;H,CF3,H,H,Me],[ZB152;H,CF2H,H,H,Me],[ZB153;H,CFH2,H,H,Me],[ZB154;H,F,H,H,Me],[ZB155;H,Cl,H,H,Me],[ZB156;H,Br,H,H,Me],[ZB157;H,CN,H,H,Me],[ZB158;H,Ph,H,H,Me],[ZB159;H,OPh,H,H,Me],[ZB160;H,c-Pr,H,H,Me],[ZB161;H,c-Pen,H,H,Me],[ZB162;H,c-Hex,H,H,Me],[ZB163;H,H,Me,H,Me],[ZB164;H,H,Et,H,Me],[ZB165;H,H,Pr,H,Me],[ZB166;H,H,i-Pr,H,Me],[ZB167;H,H,t-Bu,H,Me],[ZB168;H,H,OMe,H,Me],[ZB169;H,H,OEt,H,Me],[ZB170;H,H,OPr,H,Me],[ZB171;H,H,Oi-Pr,H,Me],[ZB172;H,H,CF3,H,Me],[ZB173;H,H,CF2H,H,Me],[ZB174;H,H,CFH2,H,Me],[ZB175;H,H,F,H,Me],[ZB176;H,H,Cl,H,Me],[ZB177;H,H,Br,H,Me],[ZB178;H,H,CN,H,Me],[ZB179;H,H,Ph,H,Me],[ZB180;H,H,OPh,H,Me],[ZB181;H,H,c-Pr,H,Me],[ZB182;H,H,c-Pen,H,Me],[ZB183;H,H,c-Hex,H,Me],[ZB184;Me,H,H,H,OMe],[ZB185;F,H,H,H,OMe],[ZB186;Cl,H,H,H,OMe],[ZB187;H,Me,H,H,OMe],[ZB188;H,Et,H,H,OMe],[ZB189;H,Pr,H,H,OMe],[ZB190;H,i-Pr,H,H,OMe],[ZB191;H,t-Bu,H,H,OMe],[ZB192;H,OMe,H,H,OMe],[ZB193;H,OEt,H,H,OMe],[ZB194;H,OPr,H,H,OMe],[ZB195;H,Oi-Pr,H,H,OMe],[ZB196;H,CF3,H,H,OMe],[ZB197;H,CF2H,H,H,OMe],[ZB198;H,CFH2,H,H,OMe],[ZB199;H,F,H,H,OMe],[ZB200;H,Cl,H,H,OMe],[ZB201;H,Br,H,H,OMe],[ZB202;H,CN,H,H,OMe],[ZB203;H,Ph,H,H,OMe],[ZB204;H,OPh,H,H,OMe],[ZB205;H,c-Pr,H,H,OMe],[ZB206;H,c-Pen,H,H,OMe],[ZB207;H,c-Hex,H,H,OMe],[ZB208;H,H,Me,H,OMe],[ZB209;H,H,Et,H,OMe],[ZB210;H,H,Pr,H,OMe],[ZB211;H,H,i-Pr,H,OMe],[ZB212;H,H,t-Bu,H,OMe],[ZB213;H,H,OMe,H,OMe],[ZB214;H,H,OEt,H,OMe],[ZB215;H,H,OPr,H,OMe],[ZB216;H,H,Oi-Pr,H,OMe],[ZB217;H,H,CF3,H,OMe],[ZB218;H,H,CF2H,H,OMe],[ZB219;H,H,CFH2,H,OMe],[ZB220;H,H,F,H,OMe],[ZB221;H,H,Cl,H,OMe],[ZB222;H,H,Br,H,OMe],[ZB223;H,H,CN,H,OMe],[ZB224;H,H,Ph,H,OMe],[ZB225;H,H,OPh,H,OMe],[ZB226;H,H,c-Pr,H,OMe],[ZB227;H,H,c-Pen,H,OMe],[ZB228;H,H,c-Hex,H,OMe],[ZB229;Me,H,H,H,CF3],[ZB230;F,H,H,H,CF3],[ZB231;Cl,H,H,H,CF3],[ZB232;H,Me,H,H,CF3],[ZB233;H,Et,H,H,CF3],[ZB234;H,Pr,H,H,CF3],[ZB235;H,i-Pr,H,H,CF3],[ZB236;H,t-Bu,H,H,CF3],[ZB237;H,OMe,H,H,CF3],[ZB238;H,OEt,H,H,CF3],[ZB239;H,OPr,H,H,CF3],[ZB240;H,Oi-Pr,H,H,CF3],[ZB241;H,CF3,H,H,CF3],[ZB242;H,CF2H,H,H,CF3],[ZB243;H,CFH2,H,H,CF3],[ZB244;H,F,H,H,CF3],[ZB245;H,Cl,H,H,CF3],[ZB246;H,Br,H,H,CF3],[ZB247;H,CN,H,H,CF3],[ZB248;H,Ph,H,H,CF3],[ZB249;H,OPh,H,H,CF3],[ZB250;H,c-Pr,H,H,CF3],[ZB251;H,c-Pen,H,H,CF3],[ZB252;H,c-Hex,H,H,CF3],[ZB253;H,H,Me,H,CF3],[ZB254;H,H,Et,H,CF3],[ZB255;H,H,Pr,H,CF3],[ZB256;H,H,i-Pr,H,CF3],[ZB257;H,H,t-Bu,H,CF3],[ZB258;H,H,OMe,H,CF3],[ZB259;H,H,OEt,H,CF3],[ZB260;H,H,OPr,H,CF3],[ZB261;H,H,Oi-Pr,H,CF3],[ZB262;H,H,CF3,H,CF3],[ZB263;H,H,CF2H,H,CF3],[ZB264;H,H,CFH2,H,CF3],[ZB265;H,H,F,H,CF3],[ZB266;H,H,Cl,H,CF3],[ZB267;H,H,Br,H,CF3],[ZB268;H,H,CN,H,CF3],[ZB269;H,H,Ph,H,CF3],[ZB270;H,H,OPh,H,CF3],[ZB271;H,H,c-Pr,H,CF3],[ZB272;H,H,c-Pen,H,CF3],
[ZB273;H,H,c-Hex,H,CF3],[ZB274;H,F,F,H,H],[ZB275;H,F,H,F,H],[ZB276;H,F,F,F,H],[ZB277;F,F,F,H,H],[ZB278;F,F,H,F,H],[ZB279;F,H,F,H,F],[ZB280;F,F,F,F,F],[ZB281;H,Cl,H,Cl,H],[ZB282;H,OMe,H,OMe,H],[ZB283;H,F,Cl,H,H],[ZB284;H,F,Me,H,H],[ZB285;H,F,OMe,H,H],[ZB286;H,F,CF3,H,H],[ZB287;H,Cl,F,H,H],[ZB288;H,Cl,Cl,H,H],[ZB289;H,Cl,Me,H,H],[ZB290;H,Cl,OMe,H,H],[ZB291;H,Cl,CF3,H,H],[ZB292;H,Me,F,H,H],[ZB293;H,Me,Cl,H,H],[ZB294;H,Me,Me,H,H],[ZB295;H,Me,OMe,H,H],[ZB296;H,Me,CF3,H,H],[ZB297;H,OMe,F,H,H],[ZB298;H,OMe,Cl,H,H],[ZB299;H,OMe,Me,H,H],[ZB300;H,OMe,OMe,H,H],[ZB301;H,OMe,CF3,H,H],[ZB302;H,CF3,F,H,H],[ZB303;H,CF3,Cl,H,H],[ZB304;H,CF3,F,H,H],[ZB305;H,CF3,Cl,H,H],[ZB306;H,CF3,F,H,H]
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、mが2であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX121と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、mが2であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX122と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、mが2であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX123と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、mが3であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX124と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、mが3であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX125と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、mが3であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX126と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、mが3であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX127と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、mが3であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX128と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、mが4であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX129と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、mが4であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX130と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、mが4であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX131と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、mが4であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX132と記す)。
化合物(2C)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、mが4であり、RX3、RX4、RX5、RX6、及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX133と記す)。
化合物(3C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX135と記す)。
化合物(3C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX136と記す)。
化合物(3C)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28がメトキシ基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX137と記す)。
化合物(3C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX138と記す)。
化合物(3C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX139と記す)。
化合物(3C)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX140と記す)。
化合物(3C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28がメチル基であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX141と記す)。
化合物(3C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28がフッ素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX142と記す)。
化合物(3C)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28が塩素原子であり、R6が群Yから選ばれるいずれかの置換基である化合物(以下、化合物群SX143と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がエチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX145と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX146と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX147と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX148と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX149と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX150と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX151と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX152と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX153と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX154と記す)。
化合物(1D)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX155と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX156と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がエチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX157と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX158と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX159と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX160と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX161と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX162と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX163と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX164と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX165と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX166と記す)。
化合物(1D)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX167と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX168と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がエチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX169と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX170と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX171と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメトキシ基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX172と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がシクロプロピル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX173と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子あり、RX2がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX174と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX175と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX176と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1が塩素原子あり、RX2がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX177と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX178と記す)。
化合物(1D)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX179と記す)。
化合物(2D)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX181と記す)。
化合物(2D)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX182と記す)。
化合物(2D)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX28がメトキシ基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX183と記す)。
化合物(2D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX184と記す)。
化合物(2D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX185と記す)。
化合物(2D)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX28が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX186と記す)。
化合物(2D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28がメチル基であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX187と記す)。
化合物(2D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28がフッ素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX188と記す)。
化合物(2D)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX28が塩素原子であり、RX3、RX4、RX5、RX6及びRX7が組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX189と記す)。
で示される化合物(以下、化合物(1E)と記す)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が、組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX190と記す)。
[ZC1;G1,H,H,H,H],[ZC2;G1,Me,H,H,H],[ZC3;G1,Et,H,H,H],[ZC4;G1,Pr,H,H,H],[ZC5;G1,i-Pr,H,H,H],[ZC6;G1,t-Bu,H,H,H],[ZC7;G1,OMe,H,H,H],[ZC8;G1,OEt,H,H,H],[ZC9;G1,OPr,H,H,H],[ZC10;G1,Oi-Pr,H,H,H],[ZC11;G1,CF3,H,H,H],[ZC12;G1,CF2H,H,H,H],[ZC13;G1,CFH2,H,H,H],[ZC14;G1,F,H,H,H],[ZC15;G1,Cl,H,H,H],[ZC16;G1,Br,H,H,H],[ZC17;G1,CN,H,H,H],[ZC18;G1,Ph,H,H,H],[ZC19;G1,OPh,H,H,H],[ZC20;G1,c-Pr,H,H,H],[ZC21;G1,H,Me,H,H],[ZC22;G1,H,Et,H,H],[ZC23;G1,H,Pr,H,H],[ZC24;G1,H,i-Pr,H,H],[ZC25;G1,H,t-Bu,H,H],[ZC26;G1,H,OMe,H,H],[ZC27;G1,H,OEt,H,H],[ZC28;G1,H,OPr,H,H],[ZC29;G1,H,Oi-Pr,H,H],[ZC30;G1,H,CF3,H,H],[ZC31;G1,H,CF2H,H,H],[ZC32;G1,H,CFH2,H,H],[ZC33;G1,H,F,H,H],[ZC34;G1,H,Cl,H,H],[ZC35;G1,H,Br,H,H],[ZC36;G1,H,CN,H,H],[ZC37;G1,H,Ph,H,H],[ZC38;G1,H,OPh,H,H],[ZC39;G1,H,c-Pr,H,H],[ZC40;G1,H,H,Me,H],[ZC41;G1,H,H,Et,H],[ZC42;G1,H,H,Pr,H],[ZC43;G1,H,H,i-Pr,H],[ZC44;G1,H,H,t-Bu,H],[ZC45;G1,H,H,OMe,H],[ZC46;G1,H,H,OEt,H],[ZC47;G1,H,H,OPr,H],[ZC48;G1,H,H,Oi-Pr,H],[ZC49;G1,H,H,CF3,H],[ZC50;G1,H,H,CF2H,H],[ZC51;G1,H,H,CFH2,H],[ZC52;G1,H,H,F,H],[ZC53;G1,H,H,Cl,H],[ZC54;G1,H,H,Br,H],[ZC55;G1,H,H,CN,H],[ZC56;G1,H,H,Ph,H],[ZC57;G1,H,H,OPh,H],[ZC58;G1,H,H,c-Pr,H],[ZC59;G1,H,H,H,Me],[ZC60;G1,H,H,H,Et],[ZC61;G1,H,H,H,Pr],[ZC62;G1,H,H,H,i-Pr],[ZC63;G1,H,H,H,t-Bu],[ZC64;G1,H,H,H,OMe],[ZC65;G1,H,H,H,OEt],[ZC66;G1,H,H,H,OPr],[ZC67;G1,H,H,H,Oi-Pr],[ZC68;G1,H,H,H,CF3],[ZC69;G1,H,H,H,CF2H],[ZC70;G1,H,H,H,CFH2],[ZC71;G1,H,H,H,F],[ZC72;G1,H,H,H,Cl],[ZC73;G1,H,H,H,Br],[ZC74;G1,H,H,H,CN],[ZC75;G1,H,H,H,Ph],[ZC76;G1,H,H,H,OPh],[ZC77;G1,H,H,H,c-Pr],[ZC78;G1,F,F,H,H],[ZC79;G1,F,H,F,H],[ZC80;G1,F,H,H,F],[ZC81;G1,H,F,F,H],[ZC82;G1,H,F,H,F],[ZC83;G1,H,H,F,F],[ZC84;G1,Cl,Cl,H,H],[ZC85;G1,Cl,H,Cl,H],[ZC86;G1,Cl,H,H,Cl],[ZC87;G1,H,Cl,Cl,H],[ZC88;G1,H,Cl,H,Cl],[ZC89;G1,H,H,Cl,Cl],[ZC90;G2,H,H,H,H],[ZC91;G2,Me,H,H,H],[ZC92;G2,Et,H,H,H],[ZC93;G2,Pr,H,H,H],[ZC94;G2,i-Pr,H,H,H],[ZC95;G2,t-Bu,H,H,H],[ZC96;G2,OMe,H,H,H],[ZC97;G2,OEt,H,H,H],[ZC98;G2,OPr,H,H,H],[ZC99;G2,Oi-Pr,H,H,H],[ZC100;G2,CF3,H,H,H],
[ZC101;G2,CF2H,H,H,H],[ZC102;G2,CFH2,H,H,H],[ZC103;G2,F,H,H,H],[ZC104;G2,Cl,H,H,H],[ZC105;G2,Br,H,H,H],[ZC106;G2,CN,H,H,H],[ZC107;G2,Ph,H,H,H],[ZC108;G2,OPh,H,H,H],[ZC109;G2,c-Pr,H,H,H],[ZC110;G2,H,Me,H,H],[ZC111;G2,H,Et,H,H],[ZC112;G2,H,Pr,H,H],[ZC113;G2,H,i-Pr,H,H],[ZC114;G2,H,t-Bu,H,H],[ZC115;G2,H,OMe,H,H],[ZC116;G2,H,OEt,H,H],[ZC117;G2,H,OPr,H,H],[ZC118;G2,H,Oi-Pr,H,H],[ZC119;G2,H,CF3,H,H],[ZC120;G2,H,CF2H,H,H],[ZC121;G2,H,CFH2,H,H],[ZC122;G2,H,F,H,H],[ZC123;G2,H,Cl,H,H],[ZC124;G2,H,Br,H,H],[ZC125;G2,H,CN,H,H],[ZC126;G2,H,Ph,H,H],[ZC127;G2,H,OPh,H,H],[ZC128;G2,H,c-Pr,H,H],[ZC129;G2,H,H,Me,H],[ZC130;G2,H,H,Et,H],[ZC131;G2,H,H,Pr,H],[ZC132;G2,H,H,i-Pr,H],[ZC133;G2,H,H,t-Bu,H],[ZC134;G2,H,H,OMe,H],[ZC135;G2,H,H,OEt,H],[ZC136;G2,H,H,OPr,H],[ZC137;G2,H,H,Oi-Pr,H],[ZC138;G2,H,H,CF3,H],[ZC139;G2,H,H,CF2H,H],[ZC140;G2,H,H,CFH2,H],[ZC141;G2,H,H,F,H],[ZC142;G2,H,H,Cl,H],[ZC143;G2,H,H,Br,H],[ZC144;G2,H,H,CN,H],[ZC145;G2,H,H,Ph,H],[ZC146;G2,H,H,OPh,H],[ZC147;G2,H,H,c-Pr,H],[ZC148;G2,H,H,H,Me],[ZC149;G2,H,H,H,Et],[ZC150;G2,H,H,H,Pr],[ZC151;G2,H,H,H,i-Pr],[ZC152;G2,H,H,H,t-Bu],[ZC153;G2,H,H,H,OMe],[ZC154;G2,H,H,H,OEt],[ZC155;G2,H,H,H,OPr],[ZC156;G2,H,H,H,Oi-Pr],[ZC157;G2,H,H,H,CF3],[ZC158;G2,H,H,H,CF2H],[ZC159;G2,H,H,H,CFH2],[ZC160;G2,H,H,H,F],[ZC161;G2,H,H,H,Cl],[ZC162;G2,H,H,H,Br],[ZC163;G2,H,H,H,CN],[ZC164;G2,H,H,H,Ph],[ZC165;G2,H,H,H,OPh],[ZC166;G2,H,H,H,c-Pr],[ZC167;G2,F,F,H,H],[ZC168;G2,F,H,F,H],[ZC169;G2,F,H,H,F],[ZC170;G2,H,F,F,H],[ZC171;G2,H,F,H,F],[ZC172;G2,H,H,F,F],[ZC173;G2,Cl,Cl,H,H],[ZC174;G2,Cl,H,Cl,H],[ZC175;G2,Cl,H,H,Cl],[ZC176;G2,H,Cl,Cl,H],[ZC177;G2,H,Cl,H,Cl],[ZC178;G2,H,H,Cl,Cl],[ZC179;G3,H,H,H,H],[ZC180;G3,Me,H,H,H],[ZC181;G3,Et,H,H,H],[ZC182;G3,Pr,H,H,H],[ZC183;G3,i-Pr,H,H,H],[ZC184;G3,t-Bu,H,H,H],[ZC185;G3,OMe,H,H,H],[ZC186;G3,OEt,H,H,H],[ZC187;G3,OPr,H,H,H],[ZC188;G3,Oi-Pr,H,H,H],[ZC189;G3,CF3,H,H,H],[ZC190;G3,CF2H,H,H,H],[ZC191;G3,CFH2,H,H,H],[ZC192;G3,F,H,H,H],[ZC193;G3,Cl,H,H,H],[ZC194;G3,Br,H,H,H],[ZC195;G3,CN,H,H,H],[ZC196;G3,Ph,H,H,H],[ZC197;G3,OPh,H,H,H],[ZC198;G3,c-Pr,H,H,H],[ZC199;G3,H,Me,H,H],[ZC200;G3,H,Et,H,H],
[ZC201;G3,H,Pr,H,H],[ZC202;G3,H,i-Pr,H,H],[ZC203;G3,H,t-Bu,H,H],[ZC204;G3,H,OMe,H,H],[ZC205;G3,H,OEt,H,H],[ZC206;G3,H,OPr,H,H],[ZC207;G3,H,Oi-Pr,H,H],[ZC208;G3,H,CF3,H,H],[ZC209;G3,H,CF2H,H,H],[ZC210;G3,H,CFH2,H,H],[ZC211;G3,H,F,H,H],[ZC212;G3,H,Cl,H,H],[ZC213;G3,H,Br,H,H],[ZC214;G3,H,CN,H,H],[ZC215;G3,H,Ph,H,H],[ZC216;G3,H,OPh,H,H],[ZC217;G3,H,c-Pr,H,H],[ZC218;G3,H,H,Me,H],[ZC219;G3,H,H,Et,H],[ZC220;G3,H,H,Pr,H],[ZC221;G3,H,H,i-Pr,H],[ZC222;G3,H,H,t-Bu,H],[ZC223;G3,H,H,OMe,H],[ZC224;G3,H,H,OEt,H],[ZC225;G3,H,H,OPr,H],[ZC226;G3,H,H,Oi-Pr,H],[ZC227;G3,H,H,CF3,H],[ZC228;G3,H,H,CF2H,H],[ZC229;G3,H,H,CFH2,H],[ZC230;G3,H,H,F,H],[ZC231;G3,H,H,Cl,H],[ZC232;G3,H,H,Br,H],[ZC233;G3,H,H,CN,H],[ZC234;G3,H,H,Ph,H],[ZC235;G3,H,H,OPh,H],[ZC236;G3,H,H,c-Pr,H],[ZC237;G3,H,H,H,Me],[ZC238;G3,H,H,H,Et],[ZC239;G3,H,H,H,Pr],[ZC240;G3,H,H,H,i-Pr],[ZC241;G3,H,H,H,t-Bu],[ZC242;G3,H,H,H,OMe],[ZC243;G3,H,H,H,OEt],[ZC244;G3,H,H,H,OPr],[ZC245;G3,H,H,H,Oi-Pr],[ZC246;G3,H,H,H,CF3],[ZC247;G3,H,H,H,CF2H],[ZC248;G3,H,H,H,CFH2],[ZC249;G3,H,H,H,F],[ZC250;G3,H,H,H,Cl],[ZC251;G3,H,H,H,Br],[ZC252;G3,H,H,H,CN],[ZC253;G3,H,H,H,Ph],[ZC254;G3,H,H,H,OPh],[ZC255;G3,H,H,H,c-Pr],[ZC256;G3,F,F,H,H],[ZC257;G3,F,H,F,H],[ZC258;G3,F,H,H,F],[ZC259;G3,H,F,F,H],[ZC260;G3,H,F,H,F],[ZC261;G3,H,H,F,F],[ZC262;G3,Cl,Cl,H,H],[ZC263;G3,Cl,H,Cl,H],[ZC264;G3,Cl,H,H,Cl],[ZC265;G3,H,Cl,Cl,H],[ZC266;G3,H,Cl,H,Cl],[ZC267;G3,H,H,Cl,Cl],[ZC268;G4,H,H,H,-],[ZC269;G4,Me,H,H,-],[ZC270;G4,Et,H,H,-],[ZC271;G4,Pr,H,H,-],[ZC272;G4,i-Pr,H,H,-],[ZC273;G4,OMe,H,H,-],[ZC274;G4,CF3,H,H,-],[ZC275;G4,F,H,H,-],[ZC276;G4,Cl,H,H,-],[ZC277;G4,Br,H,H,-],[ZC278;G4,CN,H,H,-],[ZC279;G4,Ph,H,H,-],[ZC280;G4,OPh,H,H,-],[ZC281;G4,c-Pr,H,H,-],[ZC282;G4,H,Me,H,-],[ZC283;G4,H,Et,H,-],[ZC284;G4,H,Pr,H,-],[ZC285;G4,H,i-Pr,H,-],[ZC286;G4,H,OMe,H,-],[ZC287;G4,H,CF3,H,-],[ZC288;G4,H,F,H,-],[ZC289;G4,H,Cl,H,-],[ZC290;G4,H,Br,H,-],[ZC291;G4,H,CN,H,-],[ZC292;G4,H,Ph,H,-],[ZC293;G4,H,OPh,H,-],[ZC294;G4,H,c-Pr,H,-],[ZC295;G4,H,H,Me,-],[ZC296;G4,H,H,Et,-],[ZC297;G4,H,H,Pr,-],[ZC298;G4,H,H,i-Pr,-],[ZC299;G4,H,H,OMe,-],[ZC300;G4,H,H,CF3,-],
[ZC301;G4,H,H,F,-],[ZC302;G4,H,H,Cl,-],[ZC303;G4,H,H,Br,-],[ZC304;G4,H,H,CN,-],[ZC305;G4,H,H,Ph,-],[ZC306;G4,H,H,OPh,-],[ZC307;G4,H,H,c-Pr,-],[ZC308;G5,H,H,H,-],[ZC309;G5,Me,H,H,-],[ZC310;G5,Et,H,H,-],[ZC311;G5,Pr,H,H,-],[ZC312;G5,i-Pr,H,H,-],[ZC313;G5,OMe,H,H,-],[ZC314;G5,CF3,H,H,-],[ZC315;G5,F,H,H,-],[ZC316;G5,Cl,H,H,-],[ZC317;G5,Br,H,H,-],[ZC318;G5,CN,H,H,-],[ZC319;G5,c-Pr,H,H,-],[ZC320;G5,H,Me,H,-],[ZC321;G5,H,Et,H,-],[ZC322;G5,H,Pr,H,-],[ZC323;G5,H,i-Pr,H,-],[ZC324;G5,H,OMe,H,-],[ZC325;G5,H,CF3,H,-],[ZC326;G5,H,F,H,-],[ZC327;G5,H,Cl,H,-],[ZC328;G5,H,Br,H,-],[ZC329;G5,H,CN,H,-],[ZC330;G5,H,Ph,H,-],[ZC331;G5,H,OPh,H,-],[ZC332;G5,H,c-Pr,H,-],[ZC333;G5,H,H,Me,-],[ZC334;G5,H,H,Et,-],[ZC335;G5,H,H,Pr,-],[ZC336;G5,H,H,i-Pr,-],[ZC337;G5,H,H,OMe,-],[ZC338;G5,H,H,CF3,-],[ZC339;G5,H,H,F,-],[ZC340;G5,H,H,Cl,-],[ZC341;G5,H,H,Br,-],[ZC342;G5,H,H,CN,-],[ZC343;G5,H,H,c-Pr,-],[ZC344;G6,H,H,H,-],[ZC345;G6,Me,H,H,-],[ZC346;G6,Et,H,H,-],[ZC347;G6,Pr,H,H,-],[ZC348;G6,i-Pr,H,H,-],[ZC349;G6,OMe,H,H,-],[ZC350;G6,CF3,H,H,-],[ZC351;G6,F,H,H,-],[ZC352;G6,Cl,H,H,-],[ZC353;G6,Br,H,H,-],[ZC354;G6,CN,H,H,-],[ZC355;G6,Ph,H,H,-],[ZC356;G6,OPh,H,H,-],[ZC357;G6,c-Pr,H,H,-],[ZC358;G6,H,Me,H,-],[ZC359;G6,H,Et,H,-],[ZC360;G6,H,Pr,H,-],[ZC361;G6,H,i-Pr,H,-],[ZC362;G6,H,OMe,H,-],[ZC363;G6,H,CF3,H,-],[ZC364;G6,H,F,H,-],[ZC365;G6,H,Cl,H,-],[ZC366;G6,H,Br,H,-],[ZC367;G6,H,CN,H,-],[ZC368;G6,H,Ph,H,-],[ZC369;G6,H,OPh,H,-],[ZC370;G6,H,c-Pr,H,-],[ZC371;G6,H,H,Me,-],[ZC372;G6,H,H,Et,-],[ZC373;G6,H,H,Pr,-],[ZC374;G6,H,H,i-Pr,-],[ZC375;G6,H,H,OMe,-],[ZC376;G6,H,H,CF3,-],[ZC377;G6,H,H,F,-],[ZC378;G6,H,H,Cl,-],[ZC379;G6,H,H,Br,-],[ZC380;G6,H,H,CN,-],[ZC381;G6,H,H,c-Pr,-],[ZC382;G7,H,H,H,-],[ZC383;G7,Me,H,H,-],[ZC384;G7,Et,H,H,-],[ZC385;G7,Pr,H,H,-],[ZC386;G7,i-Pr,H,H,-],[ZC387;G7,OMe,H,H,-],[ZC388;G7,CF3,H,H,-],[ZC389;G7,F,H,H,-],[ZC390;G7,Cl,H,H,-],[ZC391;G7,Br,H,H,-],[ZC392;G7,CN,H,H,-],[ZC393;G7,Ph,H,H,-],[ZC394;G7,OPh,H,H,-],[ZC395;G7,c-Pr,H,H,-],[ZC396;G7,H,Me,H,-],[ZC397;G7,H,Et,H,-],[ZC398;G7,H,Pr,H,-],[ZC399;G7,H,i-Pr,H,-],[ZC400;G7,H,OMe,H,-],
[ZC401;G7,H,CF3,H,-],[ZC402;G7,H,F,H,-],[ZC403;G7,H,Cl,H,-],[ZC404;G7,H,Br,H,-],[ZC405;G7,H,CN,H,-],[ZC406;G7,H,Ph,H,-],[ZC407;G7,H,OPh,H,-],[ZC408;G7,H,c-Pr,H,-],[ZC409;G7,H,H,Me,-],[ZC410;G7,H,H,Et,-],[ZC411;G7,H,H,Pr,-],[ZC412;G7,H,H,i-Pr,-],[ZC413;G7,H,H,OMe,-],[ZC414;G7,H,H,CF3,-],[ZC415;G7,H,H,F,-],[ZC416;G7,H,H,Cl,-],[ZC417;G7,H,H,Br,-],[ZC418;G7,H,H,CN,-],[ZC419;G7,H,H,c-Pr,-],[ZC420;G8,H,H,H,-],[ZC421;G8,Me,H,H,-],[ZC422;G8,Et,H,H,-],[ZC423;G8,Pr,H,H,-],[ZC424;G8,i-Pr,H,H,-],[ZC425;G8,OMe,H,H,-],[ZC426;G8,CF3,H,H,-],[ZC427;G8,F,H,H,-],[ZC428;G8,Cl,H,H,-],[ZC429;G8,Br,H,H,-],[ZC430;G8,CN,H,H,-],[ZC431;G8,c-Pr,H,H,-],[ZC432;G8,H,Me,H,-],[ZC433;G8,H,Et,H,-],[ZC434;G8,H,Pr,H,-],[ZC435;G8,H,i-Pr,H,-],[ZC436;G8,H,OMe,H,-],[ZC437;G8,H,CF3,H,-],[ZC438;G8,H,F,H,-],[ZC439;G8,H,Cl,H,-],[ZC440;G8,H,Br,H,-],[ZC441;G8,H,CN,H,-],[ZC442;G8,H,Ph,H,-],[ZC443;G8,H,OPh,H,-],[ZC444;G8,H,c-Pr,H,-],[ZC445;G8,H,H,Me,-],[ZC446;G8,H,H,Et,-],[ZC447;G8,H,H,Pr,-],[ZC448;G8,H,H,i-Pr,-],[ZC449;G8,H,H,OMe,-],[ZC450;G8,H,H,CF3,-],[ZC451;G8,H,H,F,-],[ZC452;G8,H,H,Cl,-],[ZC453;G8,H,H,Br,-],[ZC454;G8,H,H,CN,-],[ZC455;G8,H,H,c-Pr,-],[ZC456;G9,H,H,H,-],[ZC457;G9,Me,H,H,-],[ZC458;G9,Et,H,H,-],[ZC459;G9,Pr,H,H,-],[ZC460;G9,i-Pr,H,H,-],[ZC461;G9,OMe,H,H,-],[ZC462;G9,CF3,H,H,-],[ZC463;G9,F,H,H,-],[ZC464;G9,Cl,H,H,-],[ZC465;G9,Br,H,H,-],[ZC466;G9,CN,H,H,-],[ZC467;G9,Ph,H,H,-],[ZC468;G9,OPh,H,H,-],[ZC469;G9,c-Pr,H,H,-],[ZC470;G9,H,Me,H,-],[ZC471;G9,H,Et,H,-],[ZC472;G9,H,Pr,H,-],[ZC473;G9,H,i-Pr,H,-],[ZC474;G9,H,OMe,H,-],[ZC475;G9,H,CF3,H,-],[ZC476;G9,H,F,H,-],[ZC477;G9,H,Cl,H,-],[ZC478;G9,H,Br,H,-],[ZC479;G9,H,CN,H,-],[ZC480;G9,H,Ph,H,-],[ZC481;G9,H,OPh,H,-],[ZC482;G9,H,c-Pr,H,-],[ZC483;G9,H,H,Me,-],[ZC484;G9,H,H,Et,-],[ZC485;G9,H,H,Pr,-],[ZC486;G9,H,H,i-Pr,-],[ZC487;G9,H,H,OMe,-],[ZC488;G9,H,H,CF3,-],[ZC489;G9,H,H,F,-],[ZC490;G9,H,H,Cl,-],[ZC491;G9,H,H,Br,-],[ZC492;G9,H,H,CN,-],[ZC493;G9,H,H,c-Pr,-],[ZC494;G10,H,H,H,-],[ZC495;G10,Me,H,H,-],[ZC496;G10,Et,H,H,-],[ZC497;G10,Pr,H,H,-],[ZC498;G10,i-Pr,H,H,-],[ZC499;G10,OMe,H,H,-],[ZC500;G10,CF3,H,H,-],
[ZC501;G10,F,H,H,-],[ZC502;G10,Cl,H,H,-],[ZC503;G10,Br,H,H,-],[ZC504;G10,CN,H,H,-],[ZC505;G10,Ph,H,H,-],[ZC506;G10,OPh,H,H,-],[ZC507;G10,c-Pr,H,H,-],[ZC508;G10,H,Me,H,-],[ZC509;G10,H,Et,H,-],[ZC510;G10,H,Pr,H,-],[ZC511;G10,H,i-Pr,H,-],[ZC512;G10,H,OMe,H,-],[ZC513;G10,H,CF3,H,-],[ZC514;G10,H,F,H,-],[ZC515;G10,H,Cl,H,-],[ZC516;G10,H,Br,H,-],[ZC517;G10,H,CN,H,-],[ZC518;G10,H,Ph,H,-],[ZC519;G10,H,OPh,H,-],[ZC520;G10,H,c-Pr,H,-],[ZC521;G10,H,H,Me,-],[ZC522;G10,H,H,Et,-],[ZC523;G10,H,H,Pr,-],[ZC524;G10,H,H,i-Pr,-],[ZC525;G10,H,H,OMe,-],[ZC526;G10,H,H,CF3,-],[ZC527;G10,H,H,F,-],[ZC528;G10,H,H,Cl,-],[ZC529;G10,H,H,Br,-],[ZC530;G10,H,H,CN,-],[ZC531;G10,H,H,Ph,-],[ZC532;G10,H,H,OPh,-],[ZC533;G10,H,H,c-Pr,-],[ZC534;G11,H,H,H,-],[ZC535;G11,Me,H,H,-],[ZC536;G11,Et,H,H,-],[ZC537;G11,Pr,H,H,-],[ZC538;G11,i-Pr,H,H,-],[ZC539;G11,OMe,H,H,-],[ZC540;G11,CF3,H,H,-],[ZC541;G11,F,H,H,-],[ZC542;G11,Cl,H,H,-],[ZC543;G11,Br,H,H,-],[ZC544;G11,CN,H,H,-],[ZC545;G11,Ph,H,H,-],[ZC546;G11,OPh,H,H,-],[ZC547;G11,c-Pr,H,H,-],[ZC548;G11,H,Me,H,-],[ZC549;G11,H,Et,H,-],[ZC550;G11,H,Pr,H,-],[ZC551;G11,H,i-Pr,H,-],[ZC552;G11,H,OMe,H,-],[ZC553;G11,H,CF3,H,-],[ZC554;G11,H,F,H,-],[ZC555;G11,H,Cl,H,-],[ZC556;G11,H,Br,H,-],[ZC557;G11,H,CN,H,-],[ZC558;G11,H,Ph,H,-],[ZC559;G11,H,OPh,H,-],[ZC560;G11,H,c-Pr,H,-],[ZC561;G11,H,H,Me,-],[ZC562;G11,H,H,Et,-],[ZC563;G11,H,H,Pr,-],[ZC564;G11,H,H,i-Pr,-],[ZC565;G11,H,H,OMe,-],[ZC566;G11,H,H,CF3,-],[ZC567;G11,H,H,F,-],[ZC568;G11,H,H,Cl,-],[ZC569;G11,H,H,Br,-],[ZC570;G11,H,H,CN,-],[ZC571;G11,H,H,Ph,-],[ZC572;G11,H,H,OPh,-],[ZC573;G11,H,H,c-Pr,-],[ZC574;G12,H,H,H,-],[ZC575;G12,Me,H,H,-],[ZC576;G12,Et,H,H,-],[ZC577;G12,Pr,H,H,-],[ZC578;G12,i-Pr,H,H,-],[ZC579;G12,t-Bu,H,H,-],[ZC580;G12,CF3,H,H,-],[ZC581;G12,CHF2,H,H,-],[ZC582;G12,CH2F,H,H,-],[ZC583;G12,Ph,H,H,-],[ZC584;G12,c-Pr,H,H,-],[ZC585;G12,c-Bu,H,H,-],[ZC586;G12,c-Pen,H,H,-],[ZC587;G12,C-Hex,H,H,-],[ZC588;G12,Me,Me,H,-],[ZC589;G12,Me,Et,H,-],[ZC590;G12,Me,Pr,H,-],[ZC591;G12,Me,i-Pr,H,-],[ZC592;G12,Me,OMe,H,-],[ZC593;G12,Me,CF3,H,-],[ZC594;G12,Me,F,H,-],[ZC595;G12,Me,Cl,H,-],[ZC596;G12,Me,Br,H,-],[ZC597;G12,Me,CN,H,-],[ZC598;G12,Me,c-Pr,H,-],[ZC599;G12,Me,H,Me,-],[ZC600;G12,Me,H,Et,-],
[ZC601;G12,Me,H,Pr,-],[ZC602;G12,Me,H,i-Pr,-],[ZC603;G12,Me,H,OMe,-],[ZC604;G12,Me,H,CF3,-],[ZC605;G12,Me,H,F,-],[ZC606;G12,Me,H,Cl,-],[ZC607;G12,Me,H,Br,-],[ZC608;G12,Me,H,CN,-],[ZC609;G12,Me,H,c-Pr,-],[ZC610;G13,H,H,H,-],[ZC611;G13,Me,H,H,-],[ZC612;G13,Et,H,H,-],[ZC613;G13,Pr,H,H,-],[ZC614;G13,i-Pr,H,H,-],[ZC615;G13,t-Bu,H,H,-],[ZC616;G13,OMe,H,H,-],[ZC617;G13,OEt,H,H,-],[ZC618;G13,OPr,H,H,-],[ZC619;G13,Oi-Pr,H,H,-],[ZC620;G13,CF3,H,H,-],[ZC621;G13,CF2H,H,H,-],[ZC622;G13,CFH2,H,H,-],[ZC623;G13,F,H,H,-],[ZC624;G13,Cl,H,H,-],[ZC625;G13,Br,H,H,-],[ZC626;G13,CN,H,H,-],[ZC627;G13,Ph,H,H,-],[ZC628;G13,OPh,H,H,-],[ZC629;G13,c-Pr,H,H,-],[ZC630;G13,H,Me,H,-],[ZC631;G13,H,Et,H,-],[ZC632;G13,H,Pr,H,-],[ZC633;G13,H,i-Pr,H,-],[ZC634;G13,H,t-Bu,H,-],[ZC635;G13,H,OMe,H,-],[ZC636;G13,H,OEt,H,-],[ZC637;G13,H,OPr,H,-],[ZC638;G13,H,Oi-Pr,H,-],[ZC639;G13,H,CF3,H,-],[ZC640;G13,H,CF2H,H,-],[ZC641;G13,H,CFH2,H,-],[ZC642;G13,H,F,H,-],[ZC643;G13,H,Cl,H,-],[ZC644;G13,H,Br,H,-],[ZC645;G13,H,CN,H,-],[ZC646;G13,H,Ph,H,-],[ZC647;G13,H,OPh,H,-],[ZC648;G13,H,c-Pr,H,-],[ZC649;G13,H,H,Me,-],[ZC650;G13,H,H,Et,-],[ZC651;G13,H,H,Pr,-],[ZC652;G13,H,H,i-Pr,-],[ZC653;G13,H,H,t-Bu,-],[ZC654;G13,H,H,OMe,-],[ZC655;G13,H,H,OEt,-],[ZC656;G13,H,H,OPr,-],[ZC657;G13,H,H,Oi-Pr,-],[ZC658;G13,H,H,CF3,-],[ZC659;G13,H,H,CF2H,-],[ZC660;G13,H,H,CFH2,-],[ZC661;G13,H,H,F,-],[ZC662;G13,H,H,Cl,-],[ZC663;G13,H,H,Br,-],[ZC664;G13,H,H,CN,-],[ZC665;G13,H,H,Ph,-],[ZC666;G13,H,H,OPh,-],[ZC667;G13,H,H,c-Pr,-],[ZC668;G13,CH(Me)Et,H,H,-],[ZC669;G13,CH(Et)2,H,H,-],[ZC670;G13,CH2(i-Pr),H,H,-],[ZC671;G13,C(Me)=CH(Me),H,H,-],[ZC672;G13,C(Me)=CH2,H,H,-],[ZC673;G13,CH=CH(Me),H,H,-],[ZC674;G13,CH=CH2,H,H,-],[ZC675;G13,CC(c-Pr),H,H,-],[ZC676;G13,CC(Me),H,H,-],[ZC677;G13,CHF2,H,H,-],[ZC678;G13,CF2Me,H,H,-],[ZC679;G13,CF2CF3,H,H,-],[ZC680;G13,C(CF3)CH2,H,H,-],[ZC681;G13,CF2Cl,H,H,-],[ZC682;G13,CH(Me)CF3,H,H,-],[ZC683;G13,c-Bu,H,H,-],[ZC684;G13,c-Pen,H,H,-],[ZC685;G13,c-Hex,H,H,-],[ZC686;G13,1-Me-(c-Pr),H,H,-],[ZC687;G13,1-F-(c-Pr),H,H,-],[ZC688;G13,2,2-F2-(c-Pr),H,H,-],[ZC689;G13,I,H,H,-],[ZC690;G13,CH2CN,H,H,-],[ZC691;G13,CH2OMe,H,H,-],[ZC692;G13,CH2SMe,H,H,-],[ZC693;G13,c-hexen-1-yl,H,H,-],[ZC694;G13,OCHF2,H,H,-],[ZC695;G13,OCF3,H,H,-],[ZC696;G13,SCF3,H,H,-],[ZC697;G13,C(Me)=NOMe,H,H,-],[ZC698;G13,H,c-Bu,H,-],[ZC699;G13,H,c-Pen,H,-],[ZC700;G13,H,c-Hex,H,-],
[ZC701;G13,H,CCH,H,-],[ZC702;G13,H,CH2OMe,H,-],[ZC703;G13,H,I,H,-],[ZC704;G13,H,S(i-Pr),H,-],[ZC705;G13,Me,Me,H,-],[ZC706;G13,Pr,Me,H,-],[ZC707;G13,i-Pr,Me,H,-],[ZC708;G13,CHF2,Me,H,-],[ZC709;G13,CF3,Me,H,-],[ZC710;G13,c-Pr,Me,H,-],[ZC711;G13,c-Hex,Me,H,-],[ZC712;G13,OMe,Me,H,-],[ZC713;G13,O(i-Pr),Me,H,-],[ZC714;G13,F,Me,H,-],[ZC715;G13,Cl,Me,H,-],[ZC716;G13,Br,Me,H,-],[ZC717;G13,i-Pr,F,H,-],[ZC718;G13,Me,F,H,-],[ZC719;G13,Pr,F,H,-],[ZC720;G13,CHF2,F,H,-],[ZC721;G13,CF3,F,H,-],[ZC722;G13,c-Pr,F,H,-],[ZC723;G13,c-Hex,F,H,-],[ZC724;G13,OMe,F,H,-],[ZC725;G13,Oi-Pr,F,H,-],[ZC726;G13,F,F,H,-],[ZC727;G13,Cl,F,H,-],[ZC728;G13,Br,F,H,-],[ZC729;G13,Pr,Cl,H,-],[ZC730;G13,i-Pr,Cl,H,-],[ZC731;G13,c-Hex,Cl,H,-],[ZC732;G13,Cl,Cl,H,-],[ZC733;G13,Oi-Pr,Cl,H,-],[ZC734;G13,Me,Cl,H,-],[ZC735;G13,CHF2,Cl,H,-],[ZC736;G13,CF3,Cl,H,-],[ZC737;G13,c-Pr,Cl,H,-],[ZC738;G13,OMe,Cl,H,-],[ZC739;G13,F,Cl,H,-],[ZC740;G13,Br,Cl,H,-],[ZC741;G13,Me,Br,H,-],[ZC742;G13,c-Hex,Br,H,-],[ZC743;G13,Pr,Br,H,-],[ZC744;G13,i-Pr,Br,H,-],[ZC745;G13,CHF2,Br,H,-],[ZC746;G13,CF3,Br,H,-],[ZC747;G13,c-Pr,Br,H,-],[ZC748;G13,OMe,Br,H,-],[ZC749;G13,Oi-Pr,Br,H,-],[ZC750;G13,F,Br,H,-],[ZC751;G13,Cl,Br,H,-],[ZC752;G13,Br,Br,H,-],[ZC753;G14,H,H,H,-],[ZC754;G14,Me,H,H,-],[ZC755;G14,Et,H,H,-],[ZC756;G14,Pr,H,H,-],[ZC757;G14,i-Pr,H,H,-],[ZC758;G14,t-Bu,H,H,-],[ZC759;G14,CF3,H,H,-],[ZC760;G14,CHF2,H,H,-],[ZC761;G14,CH2F,H,H,-],[ZC762;G14,Ph,H,H,-],[ZC763;G14,c-Pr,H,H,-],[ZC764;G14,c-Bu,H,H,-],[ZC765;G14,c-Pen,H,H,-],[ZC766;G14,C-Hex,H,H,-],[ZC767;G14,Me,Me,H,-],[ZC768;G14,Me,Et,H,-],[ZC769;G14,Me,Pr,H,-],[ZC770;G14,Me,i-Pr,H,-],[ZC771;G14,Me,OMe,H,-],[ZC772;G14,Me,CF3,H,-],[ZC773;G14,Me,F,H,-],[ZC774;G14,Me,Cl,H,-],[ZC775;G14,Me,Br,H,-],[ZC776;G14,Me,CN,H,-],[ZC777;G14,Me,c-Pr,H,-],[ZC778;G14,Me,H,Me,-],[ZC779;G14,Me,H,Et,-],[ZC780;G14,Me,H,Pr,-],[ZC781;G14,Me,H,i-Pr,-],[ZC782;G14,Me,H,OMe,-],[ZC783;G14,Me,H,CF3,-],[ZC784;G14,Me,H,F,-],[ZC785;G14,Me,H,Cl,-],[ZC786;G14,Me,H,Br,-],[ZC787;G14,Me,H,CN,-],[ZC788;G14,Me,H,c-Pr,-],[ZC789;G15,H,H,H,-],[ZC790;G15,Me,H,H,-],[ZC791;G15,Et,H,H,-],[ZC792;G15,Pr,H,H,-],[ZC793;G15,i-Pr,H,H,-],[ZC794;G15,OMe,H,H,-],[ZC795;G15,CF3,H,H,-],[ZC796;G15,F,H,H,-],[ZC797;G15,Cl,H,H,-],[ZC798;G15,Br,H,H,-],[ZC799;G15,CN,H,H,-],[ZC800;G15,Ph,H,H,-],
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[ZC1201;G27,Me,H,H,-],[ZC1202;G27,Et,H,H,-],[ZC1203;G27,Pr,H,H,-],[ZC1204;G27,i-Pr,H,H,-],[ZC1205;G27,CF3,H,H,-],[ZC1206;G27,c-Pr,H,H,-],[ZC1207;G27,Me,Me,H,-],[ZC1208;G27,Me,Et,H,-],[ZC1209;G27,Me,Pr,H,-],[ZC1210;G27,Me,i-Pr,H,-],[ZC1211;G27,Me,OMe,H,-],[ZC1212;G27,Me,CF3,H,-],[ZC1213;G27,Me,F,H,-],[ZC1214;G27,Me,Cl,H,-],[ZC1215;G27,Me,CN,H,-],[ZC1216;G27,Me,Ph,H,-],[ZC1217;G27,Me,c-Pr,H,-],[ZC1218;G27,Me,H,Me,-],[ZC1219;G27,Me,H,Et,-],[ZC1220;G27,Me,H,Pr,-],[ZC1221;G27,Me,H,i-Pr,-],[ZC1222;G27,Me,H,OMe,-],[ZC1223;G27,Me,H,CF3,-],[ZC1224;G27,Me,H,F,-],[ZC1225;G27,Me,H,Cl,-],[ZC1226;G27,Me,H,CN,-],[ZC1227;G27,Me,H,Ph,-],[ZC1228;G27,Me,H,c-Pr,-],[ZC1229;G28,H,H,H,-],[ZC1230;G28,Me,H,H,-],[ZC1231;G28,Et,H,H,-],[ZC1232;G28,Pr,H,H,-],[ZC1233;G28,i-Pr,H,H,-],[ZC1234;G28,CF3,H,H,-],[ZC1235;G28,c-Pr,H,H,-],[ZC1236;G28,Me,Me,H,-],[ZC1237;G28,Me,Et,H,-],[ZC1238;G28,Me,Pr,H,-],[ZC1239;G28,Me,i-Pr,H,-],[ZC1240;G28,Me,OMe,H,-],[ZC1241;G28,Me,CF3,H,-],[ZC1242;G28,Me,F,H,-],[ZC1243;G28,Me,Cl,H,-],[ZC1244;G28,Me,CN,H,-],[ZC1245;G28,Me,Ph,H,-],[ZC1246;G28,Me,c-Pr,H,-],[ZC1247;G28,Me,H,Me,-],[ZC1248;G28,Me,H,Et,-],[ZC1249;G28,Me,H,Pr,-],[ZC1250;G28,Me,H,i-Pr,-],[ZC1251;G28,Me,H,OMe,-],[ZC1252;G28,Me,H,CF3,-],[ZC1253;G28,Me,H,F,-],[ZC1254;G28,Me,H,Cl,-],[ZC1255;G28,Me,H,CN,-],[ZC1256;G28,Me,H,c-Pr,-],[ZC1257;G29,H,H,H,-],[ZC1258;G29,Me,H,H,-],[ZC1259;G29,Et,H,H,-],[ZC1260;G29,Pr,H,H,-],[ZC1261;G29,i-Pr,H,H,-],[ZC1262;G29,OMe,H,H,-],[ZC1263;G29,CF3,H,H,-],[ZC1264;G29,F,H,H,-],[ZC1265;G29,Cl,H,H,-],[ZC1266;G29,CN,H,H,-],[ZC1267;G29,c-Pr,H,H,-],[ZC1268;G29,H,Me,H,-],[ZC1269;G29,H,Et,H,-],[ZC1270;G29,H,Pr,H,-],[ZC1271;G29,H,i-Pr,H,-],[ZC1272;G29,H,OMe,H,-],[ZC1273;G29,H,CF3,H,-],[ZC1274;G29,H,F,H,-],[ZC1275;G29,H,Cl,H,-],[ZC1276;G29,H,CN,H,-],[ZC1277;G29,H,Ph,H,-],[ZC1278;G29,H,c-Pr,H,-],[ZC1279;G29,H,H,Me,-],[ZC1280;G29,H,H,Et,-],[ZC1281;G29,H,H,Pr,-],[ZC1282;G29,H,H,i-Pr,-],[ZC1283;G29,H,H,OMe,-],[ZC1284;G29,H,H,CF3,-],[ZC1285;G29,H,H,F,-],[ZC1286;G29,H,H,Cl,-],[ZC1287;G29,H,H,CN,-],[ZC1288;G29,H,H,Ph,-],[ZC1289;G29,H,H,c-Pr,-],[ZC1290;G30,H,H,-,-],[ZC1291;G30,Me,H,-,-],[ZC1292;G30,Et,H,-,-],[ZC1293;G30,Pr,H,-,-],[ZC1294;G30,i-Pr,H,-,-],[ZC1295;G30,OMe,H,-,-],[ZC1296;G30,CF3,H,-,-],[ZC1297;G30,F,H,-,-],[ZC1298;G30,Cl,H,-,-],[ZC1299;G30,CN,H,-,-],[ZC1300;G30,c-Pr,H,-,-],
[ZC1301;G30,H,Me,-,-],[ZC1302;G30,H,Et,-,-],[ZC1303;G30,H,Pr,-,-],[ZC1304;G30,H,i-Pr,-,-],[ZC1305;G30,H,OMe,-,-],[ZC1306;G30,H,CF3,-,-],[ZC1307;G30,H,F,-,-],[ZC1308;G30,H,Cl,-,-],[ZC1309;G30,H,CN,-,-],[ZC1310;G30,H,Ph,-,-],[ZC1311;G30,H,c-Pr,-,-],[ZC1312;G31,H,H,H,-],[ZC1313;G31,Me,H,H,-],[ZC1314;G31,Et,H,H,-],[ZC1315;G31,Pr,H,H,-],[ZC1316;G31,i-Pr,H,H,-],[ZC1317;G31,CF3,H,H,-],[ZC1318;G31,c-Pr,H,H,-],[ZC1319;G31,Me,Me,H,-],[ZC1320;G31,Me,Et,H,-],[ZC1321;G31,Me,Pr,H,-],[ZC1322;G31,Me,i-Pr,H,-],[ZC1323;G31,Me,OMe,H,-],[ZC1324;G31,Me,CF3,H,-],[ZC1325;G31,Me,F,H,-],[ZC1326;G31,Me,Cl,H,-],[ZC1327;G31,Me,CN,H,-],[ZC1328;G31,Me,Ph,H,-],[ZC1329;G31,Me,c-Pr,H,-],[ZC1330;G31,Me,H,Me,-],[ZC1331;G31,Me,H,Et,-],[ZC1332;G31,Me,H,Pr,-],[ZC1333;G31,Me,H,i-Pr,-],[ZC1334;G31,Me,H,OMe,-],[ZC1335;G31,Me,H,CF3,-],[ZC1336;G31,Me,H,F,-],[ZC1337;G31,Me,H,Cl,-],[ZC1338;G31,Me,H,CN,-],[ZC1339;G31,Me,H,c-Pr,-],[ZC1340;G32,H,-,-,-],[ZC1341;G32,Me,-,-,-],[ZC1342;G32,Et,-,-,-],[ZC1343;G32,Pr,-,-,-],[ZC1344;G32,i-Pr,-,-,-],[ZC1345;G32,OMe,-,-,-],[ZC1346;G32,CF3,-,-,-],[ZC1347;G32,F,-,-,-],[ZC1348;G32,Cl,-,-,-],[ZC1349;G32,Br,-,-,-],[ZC1350;G32,CN,-,-,-],[ZC1351;G32,Ph,-,-,-],[ZC1352;G32,OPh,-,-,-],[ZC1353;G32,c-Pr,-,-,-],[ZC1354;G33,H,-,-,-],[ZC1355;G33,Me,-,-,-],[ZC1356;G33,Et,-,-,-],[ZC1357;G33,Pr,-,-,-],[ZC1358;G33,i-Pr,-,-,-],[ZC1359;G33,OMe,-,-,-],[ZC1360;G33,CF3,-,-,-],[ZC1361;G33,F,-,-,-],[ZC1362;G33,Cl,-,-,-],[ZC1363;G33,Br,-,-,-],[ZC1364;G33,CN,-,-,-],[ZC1365;G33,Ph,-,-,-],[ZC1366;G33,OPh,-,-,-],[ZC1367;G33,c-Pr,-,-,-],[ZC1368;G34,H,-,-,-],[ZC1369;G34,Me,-,-,-],[ZC1370;G34,Et,-,-,-],[ZC1371;G34,Pr,-,-,-],[ZC1372;G34,i-Pr,-,-,-],[ZC1373;G34,OMe,-,-,-],[ZC1374;G34,CF3,-,-,-],[ZC1375;G34,F,-,-,-],[ZC1376;G34,Cl,-,-,-],[ZC1377;G34,Br,-,-,-],[ZC1378;G34,CN,-,-,-],[ZC1379;G34,Ph,-,-,-],[ZC1380;G34,OPh,-,-,-],[ZC1381;G34,c-Pr,-,-,-],[ZC1382;G35,H,-,-,-],[ZC1383;G35,Me,-,-,-],[ZC1384;G35,Et,-,-,-],[ZC1385;G35,Pr,-,-,-],[ZC1386;G35,i-Pr,-,-,-],[ZC1387;G35,OMe,-,-,-],[ZC1388;G35,CF3,-,-,-],[ZC1389;G35,F,-,-,-],[ZC1390;G35,Cl,-,-,-],[ZC1391;G35,Br,-,-,-],[ZC1392;G35,CN,-,-,-],[ZC1393;G35,Ph,-,-,-],[ZC1394;G35,OPh,-,-,-],[ZC1395;G35,c-Pr,-,-,-],[ZC1396;G36,Me,H,-,-],[ZC1397;G36,Et,H,-,-],[ZC1398;G36,Pr,H,-,-],[ZC1399;G36,Bu,H,-,-],[ZC1400;G36,i-Pr,H,-,-],
[ZC1401;G36,C(Me)=CH2,H,-,-],[ZC1402;G36,CHF2,H,-,-],[ZC1403;G36,CF3,H,-,-],[ZC1404;G36,c-Pr,H,-,-],[ZC1405;G36,c-Pen,H,-,-],[ZC1406;G36,c-Hex,H,-,-],[ZC1407;G36,C(Me)=NOH,H,-,-],[ZC1408;G36,C(Me)=NOEt,H,-,-],[ZC1409;G36,F,H,-,-],[ZC1410;G36,Cl,H,-,-],[ZC1411;G36,Br,H,-,-],[ZC1412;G36,Me,Cl,-,-],[ZC1413;G36,Et,Cl,-,-],[ZC1414;G36,Pr,Cl,-,-],[ZC1415;G36,Bu,Cl,-,-],[ZC1416;G36,i-Pr,Cl,-,-],[ZC1417;G36,C(Me)=CH2,Cl,-,-],[ZC1418;G36,CHF2,Cl,-,-],[ZC1419;G36,CF3,Cl,-,-],[ZC1420;G36,c-Pr,Cl,-,-],[ZC1421;G36,c-Pen,Cl,-,-],[ZC1422;G36,c-Hex,Cl,-,-],[ZC1423;G36,C(Me)=NOH,Cl,-,-],[ZC1424;G36,C(Me)=NOEt,Cl,-,-],[ZC1425;G36,F,Cl,-,-],[ZC1426;G36,Cl,Cl,-,-],[ZC1427;G36,Br,Cl,-,-],[ZC1428;G36,Me,Br,-,-],[ZC1429;G36,Et,Br,-,-],[ZC1430;G36,Pr,Br,-,-],[ZC1431;G36,Bu,Br,-,-],[ZC1432;G36,i-Pr,Br,-,-],[ZC1433;G36,C(Me)=CH2,Br,-,-],[ZC1434;G36,CHF2,Br,-,-],[ZC1435;G36,CF3,Br,-,-],[ZC1436;G36,c-Pr,Br,-,-],[ZC1437;G36,c-Pen,Br,-,-],[ZC1438;G36,c-Hex,Br,-,-],[ZC1439;G36,C(Me)=NOH,Br,-,-],[ZC1440;G36,C(Me)=NOEt,Br,-,-],[ZC1441;G36,F,Br,-,-],[ZC1442;G36,Cl,Br,-,-],[ZC1443;G36,Br,Br,-,-],[ZC1444;G36,Me,Me,-,-],[ZC1445;G36,Et,Me,-,-],[ZC1446;G36,Pr,Me,-,-],[ZC1447;G36,Bu,Me,-,-],[ZC1448;G36,i-Pr,Me,-,-],[ZC1449;G36,C(Me)=CH2,Me,-,-],[ZC1450;G36,CHF2,Me,-,-],[ZC1451;G36,CF3,Me,-,-],[ZC1452;G36,c-Pr,Me,-,-],[ZC1453;G36,c-Pen,Me,-,-],[ZC1454;G36,c-Hex,Me,-,-],[ZC1455;G36,C(Me)=NOH,Me,-,-],[ZC1456;G36,C(Me)=NOEt,Me,-,-],[ZC1457;G36,F,Me,-,-],[ZC1458;G36,Cl,Me,-,-],[ZC1459;G36,Br,Me,-,-]
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX192と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX193と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX194と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX195と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX196と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX197と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX198と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX199と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX200と記す)。
化合物(1E)において、XがCHであり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX201と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX202と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がエチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX203と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX204と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX205と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX206と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がシクロプロピル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX207と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子あり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX208と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX209と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1がフッ素原子であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX210と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子あり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX211と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX212と記す)。
化合物(1E)において、Xが窒素原子であり、Lが酸素原子であり、R1が塩素原子であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX213と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX214と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がエチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX215と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX216と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX217と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメトキシ基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX218と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がシクロプロピル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX219と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子あり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX220と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX221と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1がフッ素原子であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX222と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1が塩素原子あり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX223と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX224と記す)。
化合物(1E)において、Xが窒素原子であり、LがNHであり、R1が塩素原子であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX225と記す)。
で示される化合物(以下、化合物(2E)と記す)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が、組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX226と記す)。
化合物(2E)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX227と記す)。
化合物(2E)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX228と記す)。
化合物(2E)において、XがCHであり、Lが酸素原子であり、R1がメチル基であり、RX2がメトキシ基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX229と記す)。
化合物(2E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX230と記す)。
化合物(2E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX231と記す)。
化合物(2E)において、Xが窒素原子であり、Lが酸素原子であり、R1がメチル基であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX232と記す)。
化合物(2E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がメチル基であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX233と記す)。
化合物(2E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2がフッ素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX234と記す)。
化合物(2E)において、Xが窒素原子であり、LがNHであり、R1がメチル基であり、RX2が塩素原子であり、Gの構造並びにGの構造に対応する置換基RX8、RX9、RX10及びRX11が組合せCに記載のいずれかの組合せである化合物(以下、化合物群SX235と記す)。
[ZD1;H,H,H,H,H,H,H,H,H],[ZD2;Me,H,H,H,H,H,H,H,H],[ZD3;F,H,H,H,H,H,H,H,H],[ZD4;Cl,H,H,H,H,H,H,H,H],[ZD5;H,F,F,H,H,H,H,H,H],[ZD6;Me,F,F,H,H,H,H,H,H],[ZD7;F,F,F,H,H,H,H,H,H],[ZD8;Cl,F,F,H,H,H,H,H,H],[ZD9;H,H,H,H,H,H,H,F,F],[ZD10;Me,H,H,H,H,H,H,F,F],[ZD11;F,H,H,H,H,H,H,F,F],[ZD12;Cl,H,H,H,H,H,H,F,F],[ZD13;H,Cl,Cl,H,H,H,H,H,H],[ZD14;Me,Cl,Cl,H,H,H,H,H,H],[ZD15;F,Cl,Cl,H,H,H,H,H,H],[ZD16;Cl,Cl,Cl,H,H,H,H,H,H],[ZD17;H,H,H,H,H,H,H,Cl,Cl],[ZD18;Me,H,H,H,H,H,H,Cl,Cl],[ZD19;F,H,H,H,H,H,H,Cl,Cl],[ZD20;Cl,H,H,H,H,H,H,Cl,Cl],[ZD21;H,H,H,F,F,H,H,H,H],[ZD22;H,H,H,Me,Me,H,H,H,H],[ZD23;H,H,H,Cl,Cl,H,H,H,H],[ZD24;H,H,H,i-Pr,H,H,H,H,H],[ZD25;H,H,H,CHF2,H,H,H,H,H],[ZD26;H,H,H,CF3,H,H,H,H,H],[ZD27;H,H,H,CN,H,H,H,H,H],[ZD28;H,H,H,OH,H,H,H,H,H],[ZD29;H,H,H,OMe,H,H,H,H,H],[ZD30;H,H,H,OCHF2,H,H,H,H,H]
化合物(1F)において、R1がメチル基であり、RX2がフッ素原子であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX238と記す)。
化合物(1F)において、R1がメチル基であり、RX2が塩素原子であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX239と記す)。
化合物(1F)において、R1がメチル基であり、RX2がメトキシ基であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX240と記す)。
化合物(1F)において、R1がメチル基であり、RX2がシクロプロピル基であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX241と記す)。
化合物(1F)において、R1がフッ素原子あり、RX2がメチル基であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX242と記す)。
化合物(1F)において、R1がフッ素原子であり、RX2がフッ素原子であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX243と記す)。
化合物(1F)において、R1がフッ素原子であり、RX2が塩素原子であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX244と記す)。
化合物(1F)において、R1が塩素原子あり、RX2がメチル基であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX245と記す)。
化合物(1F)において、R1が塩素原子であり、RX2がフッ素原子であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX246と記す)。
化合物(1F)において、R1が塩素原子であり、RX2が塩素原子であり、RX12、RX13、RX14、RX15、RX16、RX17、RX18、RX19、及びRX20が組合せDに記載のいずれかの組合せである化合物(以下、化合物群SX247と記す)。
[ZE1;H,H,H,H,H,H,H],[ZE2;Me,H,H,H,H,H,H],[ZE3;F,H,H,H,H,H,H],[ZE4;Cl,H,H,H,H,H,H],[ZE5;H,F,F,H,H,H,H],[ZE6;Me,F,F,H,H,H,H],[ZE7;F,F,F,H,H,H,H],[ZE8;Cl,F,F,H,H,H,H],[ZE9;H,H,H,H,H,F,F],[ZE10;Me,H,H,H,H,F,F],[ZE11;F,H,H,H,H,F,F],[ZE12;Cl,H,H,H,H,F,F],[ZE13;H,Cl,Cl,H,H,H,H],[ZE14;Me,Cl,Cl,H,H,H,H],[ZE15;F,Cl,Cl,H,H,H,H],[ZE16;Cl,Cl,Cl,H,H,H,H],[ZE17;H,H,H,H,H,Cl,Cl],[ZE18;Me,H,H,H,H,Cl,Cl],[ZE19;F,H,H,H,H,Cl,Cl],[ZE20;Cl,H,H,H,H,Cl,Cl],
化合物(2F)において、R1がメチル基であり、RX2がフッ素原子であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX250と記す)。
化合物(2F)において、R1がメチル基であり、RX2が塩素原子であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX251と記す)。
化合物(2F)において、R1がメチル基であり、RX2がメトキシ基であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX252と記す)。
化合物(2F)において、R1がメチル基であり、RX2がシクロプロピル基であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX253と記す)。
化合物(2F)において、R1がフッ素原子あり、RX2がメチル基であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX254と記す)。
化合物(2F)において、R1がフッ素原子であり、RX2がフッ素原子であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX255と記す)。
化合物(2F)において、R1がフッ素原子であり、RX2が塩素原子であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX256と記す)。
化合物(2F)において、R1が塩素原子あり、RX2がメチル基であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX257と記す)。
化合物(2F)において、R1が塩素原子であり、RX2がフッ素原子であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX258と記す)。
化合物(2F)において、R1が塩素原子であり、RX2が塩素原子であり、RX21、RX22、RX23、RX24、RX25、RX26、及びRX27が組合せEに記載のいずれかの組合せである化合物(以下、化合物群SX259と記す)。
ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩及びシリカの混合物(重量比1:1)35部と、本発明化合物Sのいずれか1種10部と、水55部とを混合し、湿式粉砕法で微粉砕することにより、製剤を得る。
本発明化合物Sのいずれか1種50部、リグニンスルホン酸カルシウム3部、ラウリル硫酸ナトリウム2部、及びシリカ45部を粉砕混合することにより、製剤を得る。
本発明化合物Sのいずれか1種5部、ポリオキシエチレンスチリルフェニルエーテル9部、ポリオキシエチレンデシルエーテル(エチレンオキシド付加数:5)5部、ドデシルベンゼンスルホン酸カルシウム6部、及びキシレン75部を混合することにより、製剤を得る。
本発明化合物Sのいずれか1種2部、シリカ1部、リグニンスルホン酸カルシウム2部、ベントナイト30部、及びカオリンクレー65部を粉砕混合し、適当量の水を加えて混練し、造粒機で造粒した後、乾燥することにより、製剤を得る。
本発明化合物Sのいずれか1種10部を、ベンジルアルコール18部とDMSO9部との混合物に混合し、そこに6.3部のGERONOL(登録商標) TE250、 Ethylan(登録商標) NS-500LQ 2.7部、及びソルベントナフサ 54部を加え、混合して製剤を得る。
本発明化合物Sのいずれか1種0.1部及びケロシン39.9部を混合溶解し、エアゾール容器に入れ、液化石油ガス(プロパン、ブタン及びイソブタンの混合物;飽和蒸気圧:0.47MPa(25℃))60部を充填することにより製剤を得る。
本発明化合物Sのいずれか1種0.2部、除虫菊抽出粕粉50部、タブ粉30部及び木粉19.8部を混合し、適量の水を加えて混練後、押出機にかけて板状シートとし、打抜機で渦巻状とすることにより製剤を得る。
試験例1~試験例8における無処理区とは、本発明化合物を含有するDMSO希釈液の代わりにDMSOを分注する以外は各々の試験例に記載されたのと同じ条件で行った試験区を表す。また、試験例9~試験例19における無処理とは、本発明化合物を含む製剤の水希釈液の散布を行わなかったことを意味する。試験例20及び試験例23における無処理区とは、供試化合物を使用しないこと以外は処理区と同じ操作をする区を意味する。
本発明化合物1-1、1-2、1-3、1-4、1-5、1-6、2-1、3-1、3-2、4-1、4-2、4-3、4-4、4-5、4-6、5-1、6-1、1-7、1-8、1-9、2-2、2-3、3-3、3-4、4-7、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、4-30、5-2、5-3、5-4、5-5、又は6-2を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめコムギ葉枯病菌の胞子を接種したYBG培地を150μL分注した。このプレートを3日間、18℃で培養しコムギ葉枯病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をコムギ葉枯病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1-2、1-7、1-8、1-9、2-3、4-7、4-9、4-13、4-14、4-15、4-16、4-18、4-19、又は4-20を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめウリ類灰色疫病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを3日間、27℃で培養しウリ類灰色疫病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をウリ類灰色疫病菌の生育度とした。その結果、本発明化合物を処理した区における生育度は、無処理区における生育度の50%以下であった。
本発明化合物1-2、2-1、4-2、4-3、4-4、4-5、6-1、1-3、1-5、1-6、1-7、1-8、1-9、2-3、3-1、3-2、3-4、4-7、4-8、4-9、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、5-1、又は5-2を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめ苗立枯病菌の胞子を接種したツァペック培地を150μL分注した。このプレートを5日間、23℃で培養し苗立枯病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値を苗立枯病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物2-1、4-2、4-3、4-4、4-5、6-1、1-5、1-7、1-8、1-9、2-3、4-1、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-19、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、5-4、又は6-2を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめトウモロコシ黒穂病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを4日間、18℃で培養しトウモロコシ黒穂病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をトウモロコシ黒穂病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1-2、2-1、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、2-2、2-3、3-1、3-2、3-3、3-4、4-1、4-6、4-7、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、4-30、5-1、5-2、5-3、5-4、5-5、又は6-2を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめオオムギ雲形病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを7日間、18℃で培養しオオムギ雲形病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をオオムギ雲形病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1-2、2-1、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、2-2、2-3、3-1、3-2、3-3、3-4、4-1、4-6、4-7、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、4-30、5-1、5-2、5-3、5-4、5-5、又は6-2を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめキュウリ灰色かび病菌の胞子を接種した完全培地を150μL分注した。このプレートを4日間、18℃で培養しキュウリ灰色かび病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をキュウリ灰色かび病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1-2、2-1、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、2-2、2-3、3-1、3-2、3-3、3-4、4-1、4-6、4-7、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、4-30、5-1、5-2、5-3、5-4、5-5、又は6-2を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめモモ黒星病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを5日間、18℃で培養しモモ黒星病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をモモ黒星病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1-2、2-1、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、2-2、2-3、3-1、3-2、3-3、3-4、4-1、4-6、4-7、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-24、4-25、4-26、4-27、4-29、4-30、5-1、5-2、5-3、5-4、又は5-5を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめイネごま葉枯病菌の胞子を接種したYB液体培地を150μL分注した。このプレートを3日間、23℃で培養しイネごま葉枯病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をイネごま葉枯病菌の生育度とした。その結果、各々の本発明化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
ダイズ(品種:黒千石)の本葉を直径1cmに切り抜きリーフディスクを作製した。24ウェルマイクロプレートの各ウェルに寒天培地(寒天濃度1.2%)を1mLずつ分注した後、各ウェルの寒天培地の上に、当該リーフディスクを1枚ずつ置いた。0.5μLのソルポール(登録商標)1200KX、DMSO4.5μL及びキシレン5μLの混合物に、供試化合物を10000ppm含有するDMSO溶液20μLを加えて混合した。得られた混合物をイオン交換水で希釈して供試化合物を所定濃度含有する混合物を調製した。得られた混合物を、リーフディスク1枚につき10μL散布した。1日後に、ミトコンドリアチトクロームbタンパク質にF129Lのアミノ酸置換を有するダイズさび病菌(Phakopsora pachyrhizi)の胞子の水懸濁液 (1.0×105/mL)を、リーフディスク上に噴霧接種した。接種後、人工気象器内(6時間点灯、18時間消灯、温度23℃、湿度60%)に置いた。1日後、リーフディスクの表面の水滴が無くなるまで風乾させ、再び人工気象器内に12日間置いた。その後、ダイズさび病の病斑面積を調査した。その結果、所定濃度を50ppmとし、供試化合物として本発明化合物1-2、2-1、3-1、3-2、4-1、4-2、4-3、4-4、4-5、4-6、5-1、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、2-2、2-3、3-3、3-4、4-1、4-6、4-7、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、5-1、5-2、5-3、5-4、5-5、及び6-2のいずれか1つを処理したリーフディスクの病斑面積は、いずれも無処理のリーフディスクの病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにオオムギ(品種;ニシノホシ)を播種し、温室で7日間栽培した。製剤例1に記載の方法に準じて製剤化された本発明化合物1-2、4-2、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、4-1、4-6、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、5-1、5-2、5-3、又は5-4を、濃度が200ppmとなるように水と混合した。得られた混合物を、上記オオムギの葉面に充分付着するように茎葉散布した。散布後オオムギを風乾し、1日後にオオムギ網斑病菌胞子の水懸濁液を噴霧接種した。接種後オオムギを昼間23℃、夜間20℃の温室内で多湿下に3日間置き、次に温室内で7日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したオオムギにおける病斑面積はいずれも、無処理のオオムギにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにコムギ(品種;シロガネ)を播種し、温室内で9日間栽培した。製剤例1に記載の方法に準じて製剤化された本発明化合物1-2、2-1、3-1、3-2、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、3-1、3-2、3-4、4-1、4-6、4-7、4-8、4-9、4-10、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、5-1、5-2、5-3、5-4、5-5、6-2、又は2-3を濃度が200ppmとなるように水と混合し、得られた混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、20℃、照明下で5~7日間栽培した後、コムギさび病菌の胞子をふりかけ接種した。接種後コムギを23℃、暗黒多湿下に1日間置いた後、20℃、照明下で8日間栽培し、病斑面積を調査した。その結果、各々の本発明化合物を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジー)を播種し、温室内で10日間栽培した。製剤例1に記載の方法に準じて製剤化された本発明化合物1-2、2-1、3-1、3-2、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、3-1、3-2、3-4、4-1、4-6、4-7、4-8、4-9、4-10、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-27、4-28、4-29、5-1、5-2、5-3、5-4、6-2、又は2-3を濃度が200ppmとなるように水と混合し、得られた混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、4日後にコムギ葉枯病菌の胞子を含む水懸濁液を噴霧接種した。接種後コムギを18℃多湿下に3日間置き、次に照明下で14日から18日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジー)を播種し、温室内で10日間栽培し、コムギ葉枯病菌胞子の水懸濁液を噴霧接種した。接種後コムギを18℃多湿下に3日間置いた後、製剤例1に記載の方法に準じて製剤化された本発明化合物1-2、2-1、3-1、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、3-1、4-1、4-6、4-7、4-10、4-12、4-13、4-14、4-15、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-27、4-28、4-29、5-1、6-2、又は2-3を濃度が200ppmとなるように水と混合し、得られた混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、照明下に14日から18日間置いた後、病斑面積を調査した。その結果、各々の本発明化合物を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにトマト(品種;パティオ)を播種し、温室内で20日間栽培した。製剤例1に記載の方法に準じて製剤化された本発明化合物2-1、3-2、4-2、4-3、4-5、1-1、1-3、1-4、1-5、1-6、1-8、1-9、3-2、4-1、4-6、4-7、4-8、4-9、4-12、4-13、4-15、4-16、4-17、4-18、4-19、4-22、4-23、4-24、4-28、4-29、5-1、5-2、又は5-4を濃度が200ppmとなるように水と混合し、得られた混合物を、上記トマトの葉面に充分付着するように茎葉散布した。散布後トマトを風乾し、1日後にトマト疫病菌の胞子を含む水懸濁液を噴霧接種した。接種後トマトを昼間23℃、夜間20℃の温室内で多湿下に1日間置き、次に温室内で4日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したトマトにおける病斑面積はいずれも、無処理のトマトにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにダイズ(品種;黒千石)を播種し、温室内で10~14日間生育させた。製剤例1に記載の方法に準じて製剤化された本発明化合物1-2、2-1、3-1、3-2、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、3-1、3-2、3-3、3-4、4-1、4-6、4-7、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、5-1、5-2、5-3、5-4、5-5、6-2、又は2-3を濃度が200ppmとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、2~5日後にダイズさび病菌胞子の水懸濁液を噴霧接種した。接種後ダイズを昼間23℃、夜間20℃の温室内で多湿下に1~2日間置き、次に温室内で12日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにダイズ(品種;黒千石)を播種し、温室内で10日間生育させ、ダイズさび病菌の胞子を含む水懸濁液を噴霧接種した。接種後ダイズを昼間23℃、夜間20℃の温室内で多湿下に1日間置き、次に温室で2日間栽培した後、製剤例1に記載の方法に準じて製剤化された本発明化合物1-2、2-1、3-1、3-2、4-2、4-3、4-4、4-5、6-1、1-1、1-3、1-5、1-6、1-7、1-8、1-9、3-1、3-2、3-3、3-4、4-1、4-7、4-8、4-9、4-10、4-12、4-14、4-15、4-16、4-17、4-18、4-19、4-20、4-22、4-24、4-29、5-1、5-4、又は2-3を濃度が200ppmとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、温室内で8日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにダイズ(品種;タチナガハ)を播種し、温室内で13日間生育させた。製剤例1に記載の方法に準じて製剤化された本発明化合物1-2、2-1、3-1、3-2、4-2、4-3、4-4、4-5、6-1、1-7、1-8、1-9、3-1、3-2、4-14、4-16、4-17、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-27、4-28、4-29、5-4、5-5、6-2、又は2-3を濃度が200ppmとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、1日後にダイズ斑点病菌胞子の水懸濁液を噴霧接種した。接種後ダイズを昼間23℃、夜間20℃の温室内で多湿下に3日間置き、次に温室内で16日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにトマト(品種;パティオ)を播種し、温室内で20日間生育させた。製剤例1に記載の方法に準じて製剤化された本発明化合物2-1、3-1、3-2、4-2、4-3、6-1、1-5、1-6、1-7、1-8、1-9、2-2、3-1、3-2、3-3、4-1、4-6、4-7、4-8、4-9、4-10、4-11、4-12、4-13、4-14、4-15、4-16、4-18、4-19、4-20、4-21、4-22、4-23、4-24、4-25、4-26、4-28、4-29、4-30、5-1、5-2、5-3、5-4、5-5、6-2、又は2-3を濃度が200ppmとなるように水と混合し、得られた混合物を、上記トマトの葉面に充分付着するように茎葉散布した。散布後トマトを風乾し、1日後にトマト輪紋病菌胞子の水懸濁液を噴霧接種した。接種後トマトを18℃、多湿下に6日間置いた後、病斑面積を調査した。その結果、各々の本発明化合物を処理したトマトにおける病斑面積はいずれも、無処理のトマトにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、インゲン(品種;長鶉菜豆)を播種し、温室内で8日間生育させた。製剤例1に記載の方法に準じて製剤化された本発明化合物1-2、2-1、3-2、4-2、4-3、4-4、4-5、6-1、1-3、1-4、1-5、1-6、1-7、1-8、1-9、3-2、3-3、3-4、4-1、4-6、4-7、4-9、4-10、4-12、4-13、4-14、4-15、4-17、4-18、4-19、4-20、4-21、4-22、4-23、4-28、4-29、5-1、又は5-2を濃度が200ppmとなるように水と混合し、得られた混合物を、上記インゲン葉面に充分付着するように茎葉散布した。散布後インゲンを風乾し、インゲン菌核病菌の菌糸含有PDA培地をインゲン葉面上に置いた。接種後全てのインゲンは夜間のみ多湿下におき、接種4日後に病斑面積を調査した。その結果、各々の本発明化合物を処理したインゲンにおける病斑面積はいずれも、無処理のインゲンにおける病斑面積の30%以下であった。
供試化合物を製剤例1に記載の方法に準じて製剤とし、これに展着剤0.03容量%含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
容器に植えたキュウリ(Cucumis sativus)苗(第2本葉展開期)にワタアブラムシ(全ステージ)約30頭を接種する。1日後、この苗に、該希釈液を10mL/苗の割合で散布する。更に5日後、生存虫数を調査し、以下の式により防除価を求める。
防除価(%)={1-(Cb×Tai)/(Cai×Tb)}×100
なお、式中の文字は以下の意味を表す。
Cb:無処理区の供試虫数
Cai:無処理区の調査時の生存虫数
Tb:処理区の供試虫数
Tai:処理区の調査時の生存虫数
所定濃度を500ppmとし、下記の本発明化合物を供試化合物として用いて試験法20に従って試験を行った結果、下記の本発明化合物はいずれも防除価90%以上を示した。
本発明化合物:1-2、2-1、3-1、3-2、4-2、4-3、6-1、1-1、1-6、1-7、1-9、4-1、4-7、4-9、4-10、4-11、4-12、4-15、4-16、4-17、4-18、4-19、4-22、4-23、4-24、4-25、4-29、5-1、6-2
供試化合物を製剤例1に記載の方法に準じて製剤とし、これにシンダイン(登録商標)0.03容量%含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
容器に植えたイネ(Oryza sativa)苗(第2葉展開期)に該希釈液を10mL/苗の割合で散布する。その後、トビイロウンカ3齢幼虫を20頭放す。6日後、生存虫数を調査し、以下の式により死虫率を求める。
死虫率(%)={1-生存虫数/20}×100
所定濃度を500ppmとし、下記の本発明化合物を供試化合物として用いて試験法21に従って試験を行った結果、下記の本発明化合物はいずれも死虫率90%以上を示した。
本発明化合物:1-2、2-1、3-1、3-2、6-1、1-6、1-7、1-9、2-2、3-3、4-7、4-14、4-15、4-16、4-17、4-18、4-19、4-22、4-29、6-2
供試化合物を製剤例1に記載の方法に準じて製剤とし、これにシンダイン(登録商標)0.03容量%含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
容器に植えたキャベツ苗(第2~3本葉展開期)に該希釈液を20mL/苗の割合で散布する。その後、この苗の茎葉部を切り取り、ろ紙を敷いた容器内に入れる。これにコナガ2齢幼虫5頭を放す。5日後、生存虫数を数え、次式より死虫率を求める。
死虫率(%)=(1-生存虫数/5)×100
所定濃度を500ppmとし、下記の本発明化合物を供試化合物として用いて試験法22に従って試験を行った結果、下記の本発明化合物はいずれも死虫率80%以上を示した。
本発明化合物:3-1、3-2、4-2、6-1、4-7、4-15、4-18、4-13、1-7、1-8、1-9、4-14、4-17、4-29、4-22、4-23、4-24、4-25
供試化合物を製剤例1に記載の方法に準じて製剤とし、これにシンダイン(登録商標)0.03容量%含有する水を加え、供試化合物を所定濃度含有する希釈液を調製する。
容器に植えたインゲンマメ(Phaseolus vulgaris)苗(第1本葉展開期)に約40頭のナミハダニ雌成虫を放つ。1日後、この苗に該希釈液を10mL/苗の割合で散布する。更に13日後、生存虫数を調査し、次式により防除価を算出する。
防除価(%)={1-(Cb×Tai)/(Cai×Tb)}×100
なお、式中の文字は以下の意味を表す。
Cb:無処理区の供試虫数
Cai:無処理区の調査時の生存虫数
Tb:処理区の供試虫数
Tai:処理区の調査時の生存虫数
所定濃度を500ppmとし、下記の本発明化合物を供試化合物として用いて試験法23に従って試験を行った結果、下記の本発明化合物はいずれも防除価90%以上を示した。
本発明化合物:1-2、2-1、3-1、3-2、4-2、6-1、1-3、1-6、2-2、2-3、3-3、4-7、4-9、4-10、4-11、4-15、4-16、4-17、4-18、4-19、4-21、4-22、4-24、4-25、4-27、4-29、5-5
Claims (10)
- 式(I):
X及びLの組合せは、
Xが窒素原子であり、Lが酸素原子又はNHである組合せ;又は、
XがCHであり、Lが酸素原子である組合せを表し、
nは、1又は2を表し、
Eは、群Aより選ばれる1以上の置換基で置換されていてもよいC6-C10アリール基、群Bより選ばれる1以上の置換基で置換されていてもよい5-10員芳香族複素環基、群Cより選ばれる1以上の置換基で置換されていてもよいC3-C7シクロアルケニル基、R3-O-N=C(R4)-、R5-C≡C-、又はR6O-を表し、
R1及びR2は、同一又は相異なり、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、メトキシ基、シクロプロピル基、又はハロゲン原子を表し、
R3は、群Gより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、又はR7CH2-を表し、
R4は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、又は水素原子を表し、
R5は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R6は、群Gより選ばれる1以上の置換基で置換されているメチル基、群Dより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又は群Eより選ばれる1以上の置換基で置換されていてもよいC3-C4シクロアルキル基を表し、
R7は、フェニル基、又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表す。
群A:C1-C6鎖式炭化水素基、C1-C3アルキルチオ基{該C1-C6鎖式炭化水素基及び該C1-C3アルキルチオ基は、群Gより選ばれる1以上の置換基で置換されていてもよい}、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、OR10、C(O)R8、C(O)OR8、C(O)NR8R9、NR8R9、C(R11)=N-OR12、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、及びニトロ基からなる群。
R8及びR9は、同一又は相異なり、群Gより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、又は水素原子を表し、
R10は、群Gより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R11は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、又は水素原子を表し、
R12は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C3鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、及び5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表す。
群B:群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C1-C6鎖式炭化水素基、C1-C3アルキルチオ基{該C1-C6鎖式炭化水素基及び該C1-C3アルキルチオ基は、群Gより選ばれる1以上の置換基で置換されていてもよい}、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、OR13、C(O)R8、C(O)OR8、C(O)NR8R9、NR8R9、C(R11)=N-OR12、ハロゲン原子、シアノ基、及びニトロ基からなる群。
R13は、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C1-C6鎖式炭化水素基{該C1-C6鎖式炭化水素基は、C3-C6シクロアルキル基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、又はトリフルオロメチル基を表す。
群C:C1-C4鎖式炭化水素基、C1-C3アルコキシ基{該C1-C4鎖式炭化水素基及び該C1-C3アルコキシ基は、1以上のハロゲン原子で置換されていてもよい}、ハロゲン原子、シアノ基、オキソ基、及び(=NOR13)からなる群。
群D:C1-C6アルコキシ基、C1-C6アルキルチオ基{該C1-C6アルコキシ基及び該C1-C6アルキルチオ基は、群Gより選ばれる1以上の置換基で置換されていてもよい}、C3-C6シクロアルキル基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基、及びヒドロキシ基からなる群。
群E:C1-C3鎖式炭化水素基、C1-C3アルコキシ基、C3-C6シクロアルキル基{該C1-C3鎖式炭化水素基、該C1-C3アルコキシ基、及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}、オキソ基、ハロゲン原子、シアノ基、及び(=NOR4)からなる群。
群F:C1-C3鎖式炭化水素基、C3-C6シクロアルキル基、C1-C3アルコキシ基、C1-C3アルキルチオ基{該C1-C3鎖式炭化水素基、該C3-C6シクロアルキル基、該C1-C3アルコキシ基、及び該C1-C3アルキルチオ基は、群Gより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基、及びヒドロキシ基からなる群。
群G:C3-C6シクロアルキル基、C1-C3アルコキシ基、及びハロゲン原子からなる群。〕
で示される化合物若しくはそのNオキシド又はそれらの塩。 - nが、1であり、
R1及びR2が、同一又は相異なり、1以上のハロゲン原子で置換されていてもよいC1-C3アルキル基、メトキシ基、又はハロゲン原子であり、
R2が、4位又は5位に結合し、
Eが、フェニル基、5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、R3-O-N=C(R4)-、R5-C≡C-、R6O-、又はC5-C6シクロアルケニル基であり、
R3が、群Gより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC3-C6シクロアルキル基、又はR7CH2-であり、
R4が、C1-C3鎖式炭化水素基、又は水素原子であり、
R5が、C1-C6鎖式炭化水素基、又はC3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、1以上のハロゲン原子で置換されていてもよい}であり、
R6が、群Iより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はC3-C4シクロアルキル基であり、
R7が、フェニル基又は5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、群Jより選ばれる1以上の置換基で置換されていてもよい}である、請求項1に記載の化合物若しくはそのNオキシド又はそれらの塩。
群H:1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、C1-C3アルコキシ基、トリフルオロメトキシ基、C3-C4シクロアルキル基、ハロゲン原子、シアノ基、及びニトロ基からなる群。
群I:C3-C6シクロアルキル基、C1-C3アルコキシ基、フェニル基{該C1-C3アルコキシ基及び該フェニル基は、1以上のハロゲン原子で置換されていてもよい}、及びハロゲン原子からなる群。
群J:C1-C3鎖式炭化水素基、C1-C3アルコキシ基{該C1-C3鎖式炭化水素基及び該C1-C3アルコキシ基は、1以上のハロゲン原子で置換されていてもよい}、C3-C6シクロアルキル基、ハロゲン原子、シアノ基、及びニトロ基からなる群。 - Eが、フェニル基、ピリジル基、チエニル基、チアゾリル基、ピラゾリル基{該フェニル基、該ピリジル基、該チエニル基、該チアゾリル基、及び該ピラゾリル基は、群Hより選ばれる1以上の置換基で置換されていてもよい}、R5-C≡C-、R6O-、又はC5-C6シクロアルケニル基である、請求項2に記載の化合物若しくはそのNオキシド又はそれらの塩。
- 請求項1~3のいずれかに記載の化合物若しくはそのNオキシド又はそれらの塩と不活性担体とを含有する農薬組成物。
- 群(a)、群(b)、群(c)及び群(d)からなる群より選ばれる1以上の成分、並びに、請求項1~3のいずれかに記載の化合物若しくはそのNオキシド又はそれらの塩を含有する組成物:
群(a):殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群;
群(b):殺菌活性成分;
群(c):植物成長調整成分;
群(d):忌避成分。 - 請求項1~3のいずれかに記載の化合物若しくはそのNオキシド若しくはそれらの塩の有効量又は請求項5に記載の組成物の有効量を植物又は土壌に処理することによる有害生物防除方法。
- 請求項1~3のいずれかに記載の化合物若しくはそのNオキシド若しくはそれらの塩の有効量又は請求項5に記載の組成物の有効量をダイズ又はダイズを生育する土壌に施用することによる、ミトコンドリアチトクロームbタンパク質にF129Lのアミノ酸置換を有するダイズさび病菌の防除方法。
- 有害生物を防除するための、請求項1~3のいずれかに記載の化合物若しくはそのNオキシド若しくはそれらの塩又は請求項5に記載の組成物の使用。
- 請求項1~3のいずれかに記載の化合物若しくはそのNオキシド若しくはそれらの塩の有効量又は請求項5に記載の組成物の有効量を保持している種子又は栄養生殖器官。
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EP22759827.3A EP4299557A1 (en) | 2021-02-26 | 2022-02-25 | Phenylacetic acid derivative, use therefor, and production intermediate thereof |
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