Classifications

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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
  • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
  • C07C57/32—Phenylacetic acid
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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
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01M—CATCHING, TRAPPING OR SCARING OF ANIMALS; APPARATUS FOR THE DESTRUCTION OF NOXIOUS ANIMALS OR NOXIOUS PLANTS
  • A01M1/00—Stationary means for catching or killing insects
  • A01M1/20—Poisoning, narcotising, or burning insects
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  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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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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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
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  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
• • A—HUMAN NECESSITIES
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  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P3/00—Fungicides
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  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/02—Acaricides
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  • A01P7/00—Arthropodicides
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  • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
  • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
  • C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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  • 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
  • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
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  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • 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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  • C07C69/66—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
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  • C07D213/00—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
  • 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
  • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/55—Acids; Esters
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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
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  • 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
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  • C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
  • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
  • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
  • C07D285/01—Five-membered rings
  • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
  • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
  • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • 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
  • C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
  • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

• Patent Document 1 describes a phenylacetic acid derivative.
• An object of the present invention is to provide a compound having an excellent control effect against pests.
• Equation (I) [In the formula, Q represents a group represented by Q1 or a group represented by Q2 ( ⁇ represents a binding site with a benzene ring). E is a C5-C6 cycloalkenyl group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group ⁇ the C6-C10 aryl group and the C6-C10 aryl group, which may be substituted with one or more substituents selected from the group D.
• the combination of R 1 and n is A combination in which R 1 is a hydrogen atom and n is 1; or Represents a combination in which R 1 is a C1-C3 chain hydrocarbon group, a methoxy group, a cyclopropyl group, or a halogen atom which may be substituted with one or more halogen atoms, and n is 0.
• R 2 represents a methyl group, a cyclopropyl group, or a halogen atom.
• R 4 represents a C1-C3 chain hydrocarbon group or a hydrogen atom which may be substituted with one or more halogen atoms.
• R 5 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, and C3-C6 which may be substituted with one or more substituents selected from group D. Cycloalkyl group, phenyl group, 5-6 membered aromatic heterocyclic group ⁇ The phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C.
• R 18- CH 2- represents R 7 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, and C3-C6 which may be substituted with one or more substituents selected from group D.
• R 6 is a methyl group substituted with one or more substituents selected from group F, a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, group D.
• R 8 and R 13 are the same or different, and are substituted with one or more substituents selected from group F, C1-C6 chain hydrocarbon groups, and one or more substituents selected from group D.
• C3-C6 cycloalkyl group, phenyl group, 5-6 membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6 membered aromatic heterocyclic group are one or more substitutions selected from group C.
• R 10- (CH 2 ) m- representing m represents 1 or 2 and represents R 10 and R 18 are the same or different
• the phenyl group or the 5-6 membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6 membered aromatic heterocyclic group are one or more selected from the group C. It may be substituted with a substituent ⁇ .
• Group A C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, C3-C6 cyclo which may be substituted with one or more substituents selected from group D.
• Alkyl group, C1-C6 alkylthio group optionally substituted with one or more substituents selected from group F, OR 14 , C (O) R 11 , C (O) OR 11 , NR 11 R 9 , C ( R 9 ) N-OR 11 , phenyl group, 5-6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6-membered aromatic heterocyclic group are one or more substituents selected from group E. May be substituted ⁇ , a group consisting of a halogen atom, a cyano group, and a nitro group.
• R 9 represents a C1-C3 chain hydrocarbon group or a hydrogen atom which may be substituted with one or more halogen atoms.
• R 11 and R 14 are the same or different, and are substituted with one or more substituents selected from group F, C1-C6 chain hydrocarbon groups, and one or more substituents selected from group D.
• Group C C1-C3 chain hydrocarbon group, C3-C4 cycloalkyl group, C1-C3 alkoxy group, and C1-C3 alkylthio group ⁇ the C1-C3 chain hydrocarbon group, the C3-C4 cycloalkyl group,
• the C1-C3 alkoxy group and the C1-C3 alkylthio group may be substituted with one or more halogen atoms ⁇ , a group consisting of a halogen atom, a cyano group, a nitro group, and a hydroxy group.
• Group D A group consisting of C1-C3 alkyl groups, halogen atoms, and cyano groups that may be substituted with one or more halogen atoms.
• Group E C1-C3 chain hydrocarbon group, C3-C4 cycloalkyl group, C1-C3 alkoxy group, and C1-C3 alkylthio group ⁇ the C3-C4 cycloalkyl group, the C1-C3 alkoxy group, and the C1.
• the C3 alkylthio group may be substituted with one or more halogen atoms ⁇ , a group consisting of a halogen atom, a cyano group, a nitro group, and a hydroxy group.
• Group F A group consisting of a C3-C4 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
• the compound represented by the formula (I) or its N oxide or an agriculturally acceptable salt.
• the compound of the present invention ).
• R 5 is one or more substituted with a substituent is C6 C1-may be chain hydrocarbon group
• one or more halogen atoms may be substituted C3-C6 cycloalkyl group selected from the group F
• phenyl group, 5-6-membered aromatic Hajime Tamaki ⁇ said phenyl group and said 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group G ⁇ , or R 18 -CH 2- and R 6 is a C2-C6 chain hydro
• R 11 and R 13 are the same or different and are substituted with one or more substituents selected from the group F, C1-C6 chain hydrocarbon groups, or one or more halogen atoms.
• a good C3-C6 cycloalkyl group, R 14 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or A phenyl group that may be substituted with one or more substituents selected from Group G.
• R 18 is a phenyl group or a 5-6-membered aromatic heterocyclic group ⁇ even if the phenyl group and the 5-6-membered aromatic heterocyclic group are substituted with one or more substituents selected from Group G. Good ⁇ , the compound according to [1], or an N oxide or an agriculturally acceptable salt thereof.
• Group G C1-C3 chain hydrocarbon group, 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 ⁇ , A group consisting of a halogen atom and a cyano group.
• the pyrazolyl group ⁇ the phenyl group, the pyridyl group, the thienyl group, the furanyl group, the pyrimidinyl group, the thiadiazolyl group, and the pyrazolyl group are substituted with one or more substituents selected from Group I.
• R 6 is a C2-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms.
• R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms.
• R 11 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms.
• R 14 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, or a C3-C4 cycloalkyl group.
• a group consisting of OR 11 , a phenyl group, a pyridyl group, and a pyrazolyl group ⁇ the phenyl group, the pyridyl group, and the pyrazolyl group may be substituted with one or more substituents selected from group G ⁇ .
• E is R 7- C ⁇ C-, phenyl group, pyridyl group, thienyl group, furanyl group, thiadiazolyl group, pyrazolyl group ⁇ the phenyl group, the pyridyl group, the thienyl group, the furanyl group, the thiadiazolyl.
• the group and the pyrazolyl group may be substituted with one or more substituents selected from group J ⁇ or pyrimidinyl group ⁇ the pyrimidinyl group is substituted with one or more substituents selected from group K.
• R 7 is a C1-C6 alkyl group or a cyclopropyl group which may be substituted with one or more halogen atoms, or an N oxide or an agriculturally acceptable salt thereof.
• Group J C1-C6 chain hydrocarbon group, C1-C3 alkoxy group ⁇ The C1-C6 chain hydrocarbon group and the C1-C3 alkoxy group are substituted with one or more substituents selected from group F.
• Group K A group consisting of a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a phenoxy group optionally substituted with one or more substituents selected from Group G, and a halogen atom.
• R 1 is a C1-C3 chain hydrocarbon group or a halogen atom which may be substituted with one or more halogen atoms.
• n is 0, The compound according to any one of [1] to [4], or an N oxide or an agriculturally acceptable salt thereof.
• Q is the group represented by Q1.
• R 1 is a methyl group n is 0, The compound according to any one of [1] to [4], or an N oxide or an agriculturally acceptable salt thereof.
• a pesticide composition containing the compound according to any one of [1] to [6], or an N oxide thereof or an agriculturally acceptable salt and an inert carrier.
• compositions containing compounds, or N oxides thereof or agriculturally acceptable salts Group (a): A group consisting of an insecticidal active ingredient, an acaricidal active ingredient, and a nematode active ingredient; Group (b): Bactericidal active ingredient; Group (c): Plant growth regulator; Group (d): Repellent component. [9] Treat the plant or soil with the compound according to any one of [1] to [6], or an effective amount of an N oxide or an agriculturally acceptable salt thereof, or the composition according to [8]. How to control pests.
• [10] Grow soybeans or soybeans using the compound according to any one of [1] to [6], or an effective amount of an N oxide or an agriculturally acceptable salt thereof, or the composition according to [8].
• [12] A seed holding the compound according to any one of [1] to [6], or an effective amount of an N oxide or an agriculturally acceptable salt thereof, or the composition according to [8].
• R 1 represents a C1-C3 chain hydrocarbon group, a methoxy group, a cyclopropyl group, or a halogen atom which may be substituted with one or more halogen atoms.
• R 12 represents a C1-C3 alkyl group. ] (Hereinafter referred to as Intermediate A).
• pests can be controlled.
• the substituent in the present invention will be described.
• the halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
• the substituent When the substituent is substituted with two or more halogen atoms, it means that the halogen atoms may be the same or different from each other.
• the notation "CX-CY" in the present specification means that the number of carbon atoms is X to Y.
• the notation "C1-C6" means that the number of carbon atoms is 1 to 6.
• the chain hydrocarbon group represents an alkyl group, an alkenyl group or an alkynyl group.
• alkyl group examples 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 and pentyl group.
• Examples include a hexyl group and a decyl group.
• Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group and a 3-.
• alkynyl group examples include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group, and 5 -Hexinyl group and 9-decynyl group can be mentioned.
• alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.
• alkylthio group examples include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, and a hexylthio group.
• Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
• Examples of the cycloalkenyl group include a cyclopentenyl group and a cyclohexenyl group.
• Examples of the aryl group include a phenyl group, an indenyl group, an indanyl group, a naphthyl group, and a tetrahydronaphthyl group.
• Examples of the aromatic heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group and a pyridyl group.
• the soybean rust fungus having an amino acid substitution of F129L in the mitochondrial cytochrome b protein has a mutation in the mitochondrial cytochrome b gene encoding the mitochondrial cytochrome protein, and the amino acid substitution of F129L occurs as a result of the mutation, resulting in QoI. It is a soybean rust fungus (scientific name: Phakopsora pachyrhizi) that is resistant to fungicides.
• the compound of the present invention and the intermediate A may have one or more stereoisomers.
• the stereoisomer include enantiomers, diastereomers, atropisomers and geometric isomers.
• the present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.
• the geometric isomer include the following structures.
• the compound 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, benzoic acid, etc. to cause hydrochloride, sulfate, nitrate, phosphate, acetate, benzoic acid, etc. May form acid addition salts.
• an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, benzoic acid, etc. to cause hydrochloride, sulfate, nitrate, phosphate, acetate, benzoic acid, etc. May form acid addition salts.
• Examples of the compound N of the present invention include the following compounds.
• E is R 7- C ⁇ C-, and R 7 may be substituted with one or more substituents selected from the group F. C1-C6 chain hydrocarbon group. , Or a compound that is a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms.
• E is R 7- C ⁇ C-, and R 7 may be substituted with one or more halogen atoms. C1-C6 chain hydrocarbon group, or one or more.
• E is R 7 -C ⁇ C-, and R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.
• E is R 7 -C ⁇ C-, and R 7 is a C1-C6 alkyl group or cyclopropyl group.
• E is a phenyl group which may be substituted with one or more substituents selected from the group A.
• E is a phenyl group which may be substituted with one or more substituents selected from the group I.
• E is a phenyl group which may be substituted with one or more substituents selected from the group J.
• E is a phenyl group which may be substituted with one or more substituents selected from the group J1.
• Group J1 includes C1-C3 alkyl groups, C1-C3 alkoxy groups ⁇ the C1-C3 alkyl groups and the C1-C3 alkoxy groups may be substituted with one or more halogen atoms ⁇ , halogen atoms, cyano groups.
• C (R 9 ) N-OR 11 is a group of compounds.
• E is the formula (III): Is the group indicated by R 24 and R 28 represent the same or different, halogen atom, or hydrogen atom.
• R 9X and R 11X represent the same or different C1-C3 alkyl groups and represent.
• R 26 is a compound which is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom.
• R 24 , R 26 , and R 28 are the same or different, and are fluorine atoms or hydrogen atoms.
• R 11Y is a compound which is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from the group F.
• E may be substituted with one or more substituents selected from group J3 or one or more substituents selected from group K1. It is a pyrimidinyl group and Group J3 is a group consisting of a C1-C3 alkyl group, a C1-C3 alkoxy group ⁇ the C1-C3 alkyl group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms ⁇ , and a halogen atom.
• Group K1 is a group consisting of a C1-C3 alkyl group which may be substituted with one or more halogen atoms, a phenoxy group which may be substituted with one or more substituents selected from the group G1, and a halogen atom.
• Group G1 is a compound that is a group consisting of a cyano group and a halogen atom.
• E is a thienyl group, a furanyl group, a thiadiazolyl group, or a pyrazolyl group ⁇ the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are selected from the group J4 1 It may be substituted with the above substituents ⁇ .
• Group J4 is a C1-C6 chain hydrocarbon group that may be substituted with one or more substituents selected from Group F, a C1-C6 alkoxy group that may be substituted with one or more halogen atoms, and a halogen atom.
• E is a thienyl group, a furanyl group, a thiadiazolyl group, or a pyrazolyl group ⁇ the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are selected from the group J5 1 It may be substituted with the above substituents ⁇ .
• Group J5 is a compound consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group F, and a halogen atom.
• E is a group represented by the formula (IV-1), a group represented by the formula (IV-2), a group represented by the formula (IV-3), and a group represented by the formula (IV-3).
• R 15 and R 16 represent C1-C3 chain hydrocarbon groups, halogen atoms, or hydrogen atoms that are the same or different and may be substituted with one or more halogen atoms.
• R 17 represents a C1-C3 chain hydrocarbon group or a hydrogen atom which may be substituted with one or more halogen atoms.
• A is a compound which is a phenyl group or a pyridyl group ⁇ the phenyl group and the pyridyl group may be substituted with one or more substituents selected from the group G ⁇ .
• E is a group represented by the formula (IV-1), a group represented by the formula (IV-2), or a group represented by the formula (IV-3), and A. Is a compound which is a phenyl group which may be substituted with one or more halogen atoms.
• E may be substituted with one or more substituents selected from group J2 and one or more substituents selected from group K.
• Pyrimidinyl group, thienyl group, furanyl group, thiadiazolyl group, pyrazolyl group ⁇ the thienyl group, the flanyl group, the thiadiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from group J4.
• E may be substituted with one or more substituents selected from group J3 and one or more substituents selected from group K1.
• Pyrimidinyl group, thienyl group, furanyl group, thiadiazolyl group, pyrazolyl group ⁇ the thienyl group, the flanyl group, the thiadiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from group J5.
• C1-C6 chain hydrocarbon group optionally substituted with one or more substituents of choice, C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, phenyl group, 5-6 members
• An aromatic heterocyclic group ⁇ the phenyl group and the 5-6 member aromatic heterocyclic group may be substituted with one or more substituents selected from Group G ⁇ , or R 18- CH 2- .
• R 18 is a phenyl group or a 5-6 membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6 membered aromatic heterocyclic group are substituted with one or more substituents selected from group G.
• R 18 is a phenyl group which may be substituted with one or more substituents selected from the group G.
• E is R 6 O-, and R 6 may be substituted with one or more substituents selected from the group F.
• C2-C6 chain hydrocarbon group, 1 A compound which is a C3-C4 cycloalkyl group which may be substituted with the above halogen atoms, or R 13 R 4 NC (O)-.
• E is R 6 O-
• R 6 is a C2-C 6 chain hydrocarbon group which may be substituted with one or more halogen atoms.
• E is R 6 O- and R 6 is a C2-C 6 chain hydrocarbon group.
• E is R 6 O- and R 6 is a C2-C6 alkyl group.
• E is a C5-C6 cycloalkenyl group in which E may be substituted with one or more substituents selected from the group D.
• E is a C5-C6 cycloalkenyl group.
• E may be substituted with a phenyl group which may be substituted with one or more substituents selected from group A, or one or more substituents selected from group A.
• a compound that is a good 5-6 member aromatic heterocyclic group may be substituted with one or more substituents selected from Group I or one or more substituents selected from Group H. A compound that is a good 5-6 member aromatic heterocyclic group.
• E may be substituted with one or more substituents selected from group J or one or more substituents selected from group I. A compound that is a good 5-6 member aromatic heterocyclic group.
• E may be substituted with one or more substituents selected from group J1 or one or more substituents selected from group I. A compound that is a good 5-6 member aromatic heterocyclic group.
• E may be substituted with one or more substituents selected from group J1 and one or more substituents selected from group J2.
• Pyridyl group, pyrimidinyl group optionally substituted with one or more substituents selected from group K, thienyl group, flanyl group, thiadiazolyl group, pyrazolyl group ⁇ the thienyl group, the flanyl group, the thiadiazolyl group, and the pyrazolyl
• the group may be substituted with one or more substituents selected from group J4 ⁇ , the group represented by the formula (IV-1), the group represented by the formula (IV-2), the group represented by the formula (IV-3).
• E may be substituted with one or more substituents selected from group J1 and one or more substituents selected from group J3.
• the group may be substituted with one or more substituents selected from group J5 ⁇ , the group represented by the formula (IV-1), the group represented by the formula (IV-2), or the group represented by the formula (IV-3).
• A is a phenyl group optionally substituted with one or more halogen atoms.
• E is a group represented by the formula (III), a pyridyl group optionally substituted with one or more substituents selected from the group J3, and one or more selected from the group K1.
• a pyrimidinyl group, a thienyl group, a flanyl group, a thiadiazolyl group, a pyrazolyl group which may be substituted with a substituent ⁇ the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are one or more selected from the group J5.
• E may be substituted with one or more substituents selected from group A, or one or more substituents selected from group A. 5-6 membered aromatic heterocyclic group, or R 7 is -C ⁇ C-, 1 or more C6 C1-may be substituted with a substituent chain hydrocarbon radical R 7 is selected from the group F, Alternatively, a compound which is a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms.
• E may be substituted with one or more substituents selected from Group I and one or more substituents selected from Group H.
• a 5-6-membered aromatic heterocyclic group, or a C1-C6 chain hydrocarbon group that is R 7- C ⁇ C- and R 7 may be substituted with one or more halogen atoms, or one or more halogens.
• E may be substituted with one or more substituents selected from group J, or one or more substituents selected from group I.
• E may be substituted with one or more substituents selected from group J1 and one or more substituents selected from group I.
• E may be substituted with one or more substituents selected from group J1 and one or more substituents selected from group J2.
• the group may be substituted with one or more substituents selected from group J4 ⁇ , the group represented by the formula (IV-1), the group represented by the formula (IV-2), the group represented by the formula (IV-3).
• R 7 is -C ⁇ C-, a compound wherein R 7 is C1-C6 chain hydrocarbon group, or a C3-C4 cycloalkyl group.
• E may be substituted with one or more substituents selected from group J1 and one or more substituents selected from group J3.
• the group may be substituted with one or more substituents selected from group J5 ⁇ , the group represented by the formula (IV-1), the group represented by the formula (IV-2), the group represented by the formula (IV-3).
• R 7 is a C1-C6 alkyl group, or a cyclopropyl group
• A is a phenyl group optionally substituted with one or more halogen atoms.
• E is a group represented by the formula (III), a pyridyl group optionally substituted with one or more substituents selected from the group J3, and one or more selected from the group K1.
• a pyrimidinyl group, a thienyl group, a flanyl group, a thiadiazolyl group, a pyrazolyl group which may be substituted with a substituent ⁇ the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are one or more selected from the group J5. It may be substituted with a substituent ⁇ , a group represented by the formula (IV-1), a group represented by the formula (IV-2), a group represented by the formula (IV-3), or R 7- C ⁇ .
• E may be substituted with one or more substituents selected from group A, or one or more substituents selected from group A.
• E may be substituted with one or more substituents selected from Group I and one or more substituents selected from Group H.
• E may be substituted with one or more substituents selected from group J and one or more substituents selected from group I.
• E may be substituted with one or more substituents selected from group J1 and one or more substituents selected from group I.
• E may be substituted with one or more substituents selected from group J1 and one or more substituents selected from group J2.
• the group may be substituted with one or more substituents selected from group J4 ⁇ , the group represented by the formula (IV-1), the group represented by the formula (IV-2), the group represented by the formula (IV-3).
• E may be substituted with one or more substituents selected from group J1 and one or more substituents selected from group J3.
• the group may be substituted with one or more substituents selected from group J5 ⁇ , the group represented by the formula (IV-1), the group represented by the formula (IV-2), the group represented by the formula (IV-3).
• R 7 is a C1-C6 alkyl group, or cyclopropyl group, and A is substituted with one or more halogen atoms.
• E is a group represented by the formula (III), a pyridyl group optionally substituted with one or more substituents selected from the group J3, and one or more selected from the group K1.
• a pyrimidinyl group, a thienyl group, a flanyl group, a thiadiazolyl group, a pyrazolyl group which may be substituted with a substituent ⁇ the thienyl group, the furanyl group, the thiadiazolyl group, and the pyrazolyl group are one or more selected from the group J5. May be substituted with a substituent ⁇ , a group represented by the formula (IV-1), a group represented by the formula (IV-2), a group represented by the formula (IV-3), a C5-C6 cycloalkenyl group.
• R 7 -C ⁇ C- where R 7 is a C1-C6 alkyl group or cyclopropyl group and A is a phenyl group optionally substituted with one or more halogen atoms.
• E is a phenyl group, a 5-6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6-membered aromatic heterocyclic group are one or more selected from the group J1. May be substituted with a substituent of ⁇ , R 7 -C ⁇ C-, or R 6 O-, where R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.
• R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F.
• E is a phenyl group, a 5-6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6-membered aromatic heterocyclic group are one or more selected from the group J1. May be substituted with a substituent of ⁇ , R 7 -C ⁇ C-, or R 6 O-, where R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.
• R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms.
• E is a phenyl group, a 5-6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6-membered aromatic heterocyclic group are one or more selected from the group J1. May be substituted with a substituent of ⁇ , R 7 -C ⁇ C-, or R 6 O-, where R 7 is a C1-C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.
• R 6 is a C2-C6 alkyl group.
• alkyl group a phenyl group optionally substituted with one or more substituents selected from group C, or R 18- CH 2- , where R 6 is substituted with one or more substituents selected from group F.
• C2-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from the group F, or C3 which may be substituted with one or more substituents selected from the group D.
• -C4 cycloalkyl group, R 7 may be substituted with one or more substituents selected from group F, C1-C6 chain hydrocarbon groups, or one or more substituents selected from group D.
• group A1 is selected from a C1-C6 chain hydrocarbon group that may be substituted with one or more substituents selected from group F, group D.
• R 11a represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F
• R 14a is one or more substituents selected from group F.
• a C1-C6 chain hydrocarbon group, a phenyl group, or a 5-6-membered aromatic heterocyclic group which may be substituted with ⁇ the phenyl group and the 5-6-membered aromatic heterocyclic group are group C.
• a compound representing ⁇ which may be substituted with one or more substituents selected from the above.
• R 18- CH 2- R 6 is (c-Pr) CH 2- , C2-C6 chain hydrocarbon group, or C3-C4 cycloalkyl group, and R 7 is C1-C6. It is a chain hydrocarbon group or C3-C6 cycloalkyl group, and R 18 is a phenyl group or a pyridyl group ⁇ the phenyl group and the pyridyl group are substituted with one or more substituents selected from the group C1.
• group A2 is one or more selected from C1-C6 chain hydrocarbon groups, C3-C6 cycloalkyl groups, OR 14b , and group E, which may be substituted with one or more halogen atoms.
• group C1 is a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms
• group F1 represents a group of C3-C4 cycloalkyl groups and halogen atoms
• R 14b is a C1-C6 chain hydrocarbon that may be substituted with one or more halogen atoms.
• R 1 is a C1-C3 chain hydrocarbon group or a halogen atom which may be substituted with one or more halogen atoms.
• a compound in which n is 0. A compound in which R 1 is a methyl group and n is 0 in any of Aspects 1 to 61 or Compound N of the present invention.
• R 1 is a hydrogen atom, n is 1, and R 2 is a methyl group or a halogen atom.
• R 1 is a C1-C3 chain hydrocarbon group or a halogen atom which may be substituted with one or more halogen atoms.
• a compound in which n is 0 and Q is the group represented by Q1.
• R 1 is a hydrogen atom, n is 1, R 2 is a methyl group or a halogen atom, and Q is indicated by Q1.
• R 1 is a hydrogen atom, n is 1, R 2 is a methyl group, and Q is a group represented by Q1.
• R 1 is a hydrogen atom, n is 1, R 2 is a chlorine atom, and Q is a group represented by Q1.
• R 1 is a C1-C3 chain hydrocarbon group or a halogen atom which may be substituted with one or more halogen atoms.
• a compound in which n is 0 and Q is the group represented by Q2.
• R 1 is a hydrogen atom, n is 1, R 2 is a methyl group or a halogen atom, and Q is indicated by Q 2.
• R 1 is a hydrogen atom, n is 1, R 2 is a methyl group, and Q is a group represented by Q 2.
• R 1 is a hydrogen atom, n is 1, R 2 is a chlorine atom, and Q is a group represented by Q 2.
• E is a C5-C6 cycloalkenyl group, a phenyl group, a 5-6-membered aromatic heterocyclic group, which may be substituted with one or more substituents selected from the group D.
• a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group, a phenyl group, a 5-6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5-
• the 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group G ⁇ or R 18- CH 2- , where R 6 is one or more selected from group F.
• a C2-C6 chain hydrocarbon group optionally substituted with a substituent, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, or R 13 R 4 NC (O)-.
• R 7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms.
• R 11 and R 13 are substituted with a C1-C6 chain hydrocarbon group, which is the same or different and may be substituted with one or more substituents selected from Group F, or one or more halogen atoms. It is a C3-C6 cycloalkyl group which may be substituted, and R 14 is substituted with a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from the group F, and one or more halogen atoms.
• the group ⁇ the phenyl group and the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group G ⁇ .
• Group G is a C1-C3 chain hydrocarbon group, 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 ⁇ ,.
• C1-C6 chain hydrocarbon group in which group H may be substituted with one or more halogen atoms, C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, OR 14 , halogen atom, cyano Group, C (R 4 ) N-OR 11 , phenyl group, and 5-6 membered aromatic heterocyclic group ⁇ The phenyl group and the 5-6 membered aromatic heterocyclic group are one or more selected from the group G.
• a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C4 cycloalkyl group optionally substituted with one or more halogen atoms, OR 14 , Halogen atom, cyano group, C (R 4 ) N-OR 11 , phenyl group, and 5-6 membered aromatic heterocyclic group ⁇ The phenyl group and the 5-6 membered aromatic heterocyclic group are group G.
• a compound which is a group consisting of ⁇ which may be substituted with one or more substituents selected from the above.
• the compound represented by the formula (A1) includes the compound represented by the formula (B1) (hereinafter referred to as the compound (B1)) and the compound represented by the formula (M1) (hereinafter referred to as the compound (M1)). It can be produced by reacting compound (denoted as M1)) in the presence of a palladium catalyst and a base.
• E 1 is a C6-C10 aryl group or a 5-10-membered aromatic heterocyclic group ⁇ the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group are selected from Group A 1 It may be 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 51 represents a desorbing group such as a chlorine atom, a bromine atom, an iodine atom and a trifuryloxy group, and other symbols have the same meanings as described above.
• the reaction is usually carried out in a solvent.
• Examples of the solvent used in the reaction include hydrocarbons such as hexane, toluene and xylene (hereinafter referred to as hydrocarbons); methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and the like.
• 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), and the like.
• 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 and the
• amides Amides (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 2 of these One or more mixtures are mentioned.
• the palladium catalyst used in the reaction include ⁇ 1,1'-bis (diphenylphosphino) ferrocene ⁇ palladium (II) dichloride.
• Examples of the base 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); hydrogen carbonate.
• Alkali metal bicarbonates such as sodium and potassium hydrogen carbonate (hereinafter referred to as alkali metal bicarbonates); sodium fluoride and tripotassium phosphate can be mentioned.
• the ratio of compound (M1) is usually 1 to 10 mol
• the ratio of palladium catalyst is usually 0.01 to 1 mol
• the ratio of base is usually 1 to 10 mol to 1 mol of compound (B1). Used.
• the reaction temperature is usually in the range of 0 to 150 ° C.
• the reaction time is usually in the range of 0.1 to 120 hours.
• the compound (A1) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• Compound (M1) is known or can be produced according to a known method.
• the compound (A1) is a compound represented by the formula (B2) (hereinafter referred to as compound (B2)) and a compound represented by the formula (M2) (hereinafter referred to as compound (M2)) of a palladium catalyst and a base. It can be produced by reacting in the presence. [In the formula, the symbols have the same meanings as described above. ] The reaction can be carried out according to the production method A by using the compound (M2) instead of the compound (B1) and using the compound (B2) instead of the compound (M1). Compound (M2) is known or can be produced according to a known method.
• the compound represented by the formula (A2) (hereinafter referred to as compound (A2)) is a compound (B1) and a compound represented by the formula (M3) (hereinafter referred to as compound (M3)) of a metal catalyst and a base. It can be produced by reacting in the presence. [In the formula, the symbols have the same meanings as described above. ] 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 of these.
• Examples of the metal catalyst used in the reaction include bis (triphenylphosphine) palladium (II) dichloride (hereinafter referred to as PdCl 2 (PPh 3 ) 2 ) and copper (I) iodide.
• Examples of the base used in the reaction include organic bases.
• the ratio of compound (M3) is usually 1 to 10 mol
• the ratio of metal catalyst is usually 0.01 to 1 mol
• the ratio of base is usually 1 to 10 mol to 1 mol of compound (B1). Used.
• the reaction temperature is usually in the range of 0 to 150 ° C.
• the reaction time is usually in the range of 0.1 to 120 hours.
• the compound (A2) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• Compound (M3) is known or can be produced according to a known method.
• the compound represented by the formula (A3) (hereinafter referred to as the compound (A3)) is the compound represented by the formula (B3) (hereinafter referred to as the compound (B3)) and the compound represented by the formula (M4) (hereinafter referred to as the compound (B3)). It can be produced by reacting with compound (denoted as M4) or a salt thereof. [In the formula, the symbols have the same meanings as described above. ] Examples of the salt of compound (M4) include 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; alcohols such as methanol and ethanol (hereinafter referred to as alcohols); and 2 of these. One or more mixtures are mentioned.
• a base may be added to the reaction.
• the base used in the reaction include organic bases; alkali metal carbonates; alkali metal hydrogen carbonates; sodium hydride and tripotassium phosphate.
• the compound (M4) is usually used in a ratio of 1 to 10 mol and the base is usually used in a ratio of 1 to 10 mol with respect to 1 mol of the compound (B3).
• the reaction temperature is usually in the range of 0 to 150 ° C.
• the reaction time is usually in the range of 0.1 to 120 hours.
• the compound (A3) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• the compound (A3) can also be produced according to the method described in International Publication No. 1998/043949 or the like.
• Compound (M4) is known or can be produced according to a known method.
• Manufacturing method E The compound represented by the formula (A4) (hereinafter referred to as compound (A4)) reacts the compound (B3) with the compound represented by the formula (M5) (hereinafter referred to as compound (M5)) or a salt thereof. It can be manufactured by. [In the formula, the symbols have the same meanings as described above. ] Examples of the salt of compound (M5) include hydrochloride and sulfate. The reaction can be carried out according to the production method D by using the compound (M5) instead of the compound (M4). Compound (M5) is known or can be produced according to a known method.
• the compound (A3) is a compound represented by the formula (B4) (hereinafter referred to as compound (B4)) and a compound represented by the formula (M6) (hereinafter referred to as compound (M6)) in the presence of a base. It can be produced by reacting. [In the formula, the symbols have the same meanings as described above. ] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof. Examples of the base include organic bases, alkali metal carbonates, alkali metal bicarbonates, sodium hydride and tripotassium phosphate.
• the compound (M6) is usually used at a ratio of 1 to 10 mol and the base is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the compound (B4).
• the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
• the reaction time is usually in the range of 0.1-48 hours.
• the compound (A3) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• Compound (M6) is known or can be produced according to a known method.
• the compound represented by the formula (A5) (hereinafter referred to as compound (A5)) is a compound (B1) and a compound represented by the formula (M8) (hereinafter referred to as compound (M8)) of 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 (provided that it represents a nitrogen atom or CR 54).
• 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 F.
• C1-C6 chain hydrocarbon group optionally substituted with, C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from group D, one or more substituents selected from group F C1-C6 alkylthio group optionally substituted with, OR 14 , C (O) R 11 , C (O) OR 11 , NR 11 R 9 , C (R 9 ) N-OR 11 , phenyl group, 5 -6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group E ⁇ , halogen atom, cyano group.
• the reaction is usually carried out in a solvent.
• the solvent used in the reaction include ethers, hydrocarbons, amides, water and a mixture of two or more thereof.
• the metal catalyst used in the reaction include copper iodide (I), copper bromide (I), copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate (I) benzene complex, and tetrakis (acetoform).
• Copper catalysts such as copper (I) hexafluorophosphate and copper (I) 2-thiophene carboxylate; nickel catalysts such as bis (cyclooctadiene) nickel (0) and nickel chloride (II).
• the base include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium fluoride and tripotassium phosphate. If necessary, a ligand and / or an alkali metal halide may be used in the reaction.
• Examples of the ligand include triphenylphosphine, xantphos, 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl, 1,1'-bis (diphenylphosphino) ferrocene, and 2-dicyclohexylphos.
• the ligand When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mol with respect to 1 mol of the compound (B1).
• the alkali metal halide include potassium fluoride, sodium fluoride, lithium chloride, sodium chloride and the like.
• the alkali metal halide When an alkali metal halide is used in the reaction, the alkali metal halide is usually used in a ratio of 0.1 to 5 mol with respect to 1 mol of the compound (B1).
• the ratio of compound (M8) is usually 1 to 10 mol
• the ratio of metal catalyst is usually 0.01 to 2 mol
• the ratio of base is usually 1 to 10 mol to 1 mol of compound (B1). Used.
• the reaction temperature is usually in the range of ⁇ 20 ° C. to 200 ° C.
• the reaction time is usually in the range of 0.1-48 hours.
• the compound (A5) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• Compound (M8) is known or can be produced according to a known method.
• the compound represented by the formula (A6) (hereinafter referred to as the compound (A6)) is the compound represented by the formula (B5) (hereinafter referred to as the compound (B5)) and the compound represented by the formula (M9) (hereinafter referred to as the compound (B5)). It can be produced by reacting compound (denoted as M9)) in the presence of phosphines and azodiesters. [In the formula, the symbols have the same meanings as described above. ] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbon ethers; halogenated hydrocarbons; amides; esters; nitriles and mixtures of two or more of these.
• Examples of phosphines include triphenylphosphine and trimethylphosphine.
• Examples of azodiesters include diethyl azodicarboxylate, diisopropyl azodicarboxylate and bis (2-methoxyethyl) azodicarboxylate.
• the reaction temperature is usually in the range of 0 to 150 ° C.
• the reaction time is usually in the range of 0.1-48 hours.
• the compound (A6) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• Compound (M9) is known or can be produced according to a known method.
• Manufacturing method J Compound (A6) can also be produced by reacting compound (B5) with a compound represented by the formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base.
• a compound represented by the formula (M10) hereinafter referred to as compound (M10)
• the reaction is usually carried out in a solvent.
• the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
• the base include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
• the compound (M10) is usually used in a ratio of 1 to 10 mol and the base is usually used in a ratio of 1 to 10 mol with respect to 1 mol of the compound (B5).
• the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
• the reaction time is usually in the range of 0.1-48 hours.
• the compound (A6) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• Compound (M10) is known or can be produced according to a known method.
• the compound represented by the formula (A7) (hereinafter referred to as the compound (A7)) is the compound represented by the formula (B6) (hereinafter referred to as the compound (B6)) and the compound represented by the formula (M11) (hereinafter referred to as the compound (B6)).
• step (K-2) a compound represented by the formula (M12)
• R 55 represents a C1-C4 alkyl group
• X 52 represents an iodine atom, a methoxysulfonyloxy, a mesyloxy group, or a tosyloxy group, and other symbols have the same meanings as described above.
• Step (K-1) is usually carried out in a solvent.
• the solvent used in the reaction include ethers, amides and a mixture of two or more thereof.
• the base used in the reaction include sodium hydride.
• the compound (M11) is usually used at a ratio of 1 mol to 10 mol and the base is usually used at a ratio of 0.5 mol to 5 mol with respect to 1 mol of the compound (B6).
• 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 100 ° C.
• the compound (B7) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• the compound (B6) and the compound (M11) are commercially available compounds or can be produced according to a known method.
• Step (K-2) is usually carried out in a solvent.
• the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
• the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, and sodium hydride.
• the compound (M12) is usually used in a ratio of 1 to 10 mol and the base is usually used in a ratio of 1 to 20 mol with respect to 1 mol of the compound (B7).
• the reaction temperature is usually in the range of ⁇ 20 to 100 ° C.
• the reaction time is usually in the range of 0.1-48 hours.
• the compound (A7) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• the compound (M12) is a commercially available compound or can be produced according to a known method.
• the compound represented by the formula (A8) includes the compound represented by the formula (B8) (hereinafter referred to as the compound (B8)) and the compound represented by the formula (M13) (hereinafter referred to as the compound (B8)).
• a step of reacting compound (M13)) in the presence of a base to obtain a compound represented by the formula (B9) (hereinafter referred to as compound (B9)) (hereinafter referred to as step (L-1)).
• step (L-2) a base
• R 56 represents a t-butyl group or an isopentyl group, and other symbols have the same meanings as described above.
• R 56 represents a t-butyl group or an isopentyl group, and other symbols have the same meanings as described above.
• Step (L-1) is usually carried out in a solvent.
• the solvent used in the reaction include ethers, amides, alcohols and mixtures of two or more of these.
• Examples of the base used in the reaction include sodium hydride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium t-butoxide.
• the compound (M13) is usually used at a ratio of 1 mol to 10 mol and the base is usually used at a ratio of 1 mol to 5 mol with respect to 1 mol of the compound (B8).
• 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 100 ° C.
• the compound (B9) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• the compound (B8) and the compound (M13) are commercially available compounds or can be produced according to a known method.
• the step (L-2) can be carried out according to the step (K-2) of the production method K by using the compound (B9) instead of the compound (B7).
• the compound represented by the formula (A9) is a compound (B1) and a compound represented by the formula (M15) (hereinafter referred to as compound (M15)) of a palladium catalyst and a base. It can be produced by reacting in the presence.
• E 2 represents a C5-C6 cycloalkenyl group that may be substituted with one or more substituents selected from Group D, and the other symbols represent the same meanings as described above.
• the reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, hydrocarbons, amides, water and a mixture of two or more thereof.
• Examples of the palladium catalyst used in the reaction include tris (dibenzylideneacetone) dipalladium (0), palladium (II) acetate and acetylacetonepalladium (II).
• Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydrogen carbonates. If necessary, a ligand and / or an alkali metal halide may be used in the reaction.
• ligand examples include tritert-butylphosphine tetrafluoroborate, triphenylphosphine, xantphos, 2,2'-bis (diphenylphosphino) -1,1'-binaphthyl, 1,1'-bis ( Diphenylphosphine) Ferrocene, 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl, 1,2-bis (diphenylphosphino) Etan, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N, N'-dimethylcyclohexane-1,2-diamine, And N, N'-dimethylethylenediamine.
• the ligand When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mol with respect to 1 mol of the compound (B1).
• alkali metal halides include potassium fluoride, sodium fluoride, lithium chloride and sodium chloride.
• the alkali metal halide When an alkali metal halide is used in the reaction, the alkali metal halide is usually used in a ratio of 0.1 to 5 mol with respect to 1 mol of the compound (B1).
• the ratio of compound (M15) is usually 1 to 10 mol
• the ratio of palladium catalyst is usually 0.01 to 1 mol
• the ratio of base is usually 1 to 10 mol to 1 mol of compound (B1). Used.
• the reaction temperature is usually in the range of 0 to 150 ° C.
• the reaction time is usually in the range of 0.1 to 120 hours.
• the compound (A9) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• the compound (A9) can also be produced according to the method described in Chem. Commun., 2013, 49, 4794.
• Compound (M15) is known or can be produced according to a known method.
• N oxide of the compound represented by the formula (I) can be produced by reacting the compound represented by the 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.
• the compound represented by the formula (B12) (hereinafter referred to as compound (B12)) is a compound represented by the formula (B10) (hereinafter referred to as compound (B10)) and the compound (M11) in the presence of a base.
• step (1-1) a step of reacting in the presence of (hereinafter referred to as step (1-2)).
• the step (1-1) can be carried out according to the step (K-1) of the production method K by using the compound (B10) instead of the compound (B6).
• the step (1-2) can be carried out according to the step (K-2) of the production method K by using the compound (B11) instead of the compound (B7).
• the compound represented by the formula (B15) is a compound represented by the formula (B13) (hereinafter referred to as compound (B13)) and the compound (M13) in the presence of a base.
• step (2-2) In the formula, the symbols have the same meanings as described above. ]
• the step (2-1) can be carried out according to the step (L-1) of the production method L by using the compound (B13) instead of the compound (B8).
• the step (2-2) can be carried out according to the step (K-2) of the production method K by using the compound (B14) instead of the compound (B7).
• the compound represented by the formula (B16) (hereinafter referred to as compound (B16)) can be produced by reacting compound (B1) with bis (pinacolato) diboron in the presence of a base and a palladium catalyst.
• the reaction is usually carried out in a solvent.
• the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, sulfoxides such as dimethyl sulfoxide (hereinafter referred to as DMSO) (hereinafter referred to as sulfoxides), and the like. Examples include nitriles and mixtures of two or more of these.
• Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates and tripotassium phosphate.
• Examples of the palladium catalyst include [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride.
• the ratio of bis (pinacolato) diboron is usually 1 to 5 mol
• the ratio of base is usually 1 to 5 mol
• the ratio of palladium catalyst is usually 0.01 to 0.5 mol with respect to 1 mol of compound (B1). It is used in the ratio of.
• the reaction temperature is usually in the range of 0 to 150 ° C. and the reaction time is usually in the range of 0.1 to 48 hours.
• the compound (B16) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
• Reference manufacturing method 4 Compound (B5) can be produced by oxidizing compound (B16).
• the reaction is usually carried out in a solvent.
• the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more of these.
• the oxidizing agent used in the reaction include metachloroperbenzoic acid and hydrogen peroxide solution. When hydrogen peroxide solution is used as the oxidizing agent, a base may be added if necessary. Examples of the base include sodium hydroxide and potassium hydroxide.
• an oxidizing agent is usually used at a ratio of 1 to 5 mol to 1 mol of compound (B16).
• the base is usually used in a ratio of 0.1 to 5 mol to 1 mol of compound (B16).
• the reaction temperature is usually in the range of ⁇ 20 to 120 ° C. and the reaction time is usually in the range of 0.1 to 48 hours.
• the compound (B5) is isolated by adding water and a reducing agent such as sodium thiosulfate to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. can do.
• Reference manufacturing method 5 The compound represented by the formula (B17) (hereinafter referred to as compound (B17)) is produced by reacting the compound (B1) with the compound represented by the formula (M14) (hereinafter referred to as compound (M14)). can do.
• R 57 represents a methyl group or an ethyl group, and other symbols have the same meanings as described above.
• the reaction can be carried out, for example, according to the method described in WO 2016/123253.
• Reference manufacturing method 6 Compound (B4) can be produced by reacting compound (B3) with hydroxylamine or a salt thereof.
• Hydroxylamine salts include, for example, hydrochlorides and sulfates. The reaction can be carried out according to Production Method D, using hydroxylamine instead of compound (M4).
• the compound of the present invention may be mixed or used in combination with one or more components (hereinafter referred to as this component) selected from the group consisting of the following groups (a), group (b), group (c) and group (d). can.
• the mixed use or combined use means that the compound of the present invention and the present component are used at the same time, separately or at intervals of time.
• the compound of the present invention and the present component may be contained in separate formulations or may be contained in one formulation.
• One aspect of the present invention contains one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound of the present invention (hereinafter, composition). It is written as A).
• Group (a) includes acetylcholine esterase inhibitors (eg carbamate pesticides, organic phosphorus pesticides), GABAergic chlorine ion channel blockers (eg phenylpyrazole pesticides), sodium channel modulators (eg pyrethroid pesticides).
• acetylcholine esterase inhibitors eg carbamate pesticides, organic phosphorus pesticides
• GABAergic chlorine ion channel blockers eg phenylpyrazole pesticides
• sodium channel modulators eg pyrethroid pesticides.
• Nicotinic acetylcholine receptor competitive modulators eg, neonicotinoid pesticides
• nicotinic acetylcholine receptor allosteric modulators glutamate-operated chlorine ion channel allosteric modulators (eg, macrolide pesticides)
• immature hormones Mimics multisite inhibitors, chord organ TRPV channel modulators, tick growth inhibitors, microbial-derived insect midgut intestinal membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation deconjugation agents, nicotinic acetylcholine receptor channels
• Blockers eg, nelystoxin pesticides
• chitin synthesis inhibitors dehulling inhibitors
• ecdison receptor agonists octopamine receptor agonists
• mitochondrial ion channel complex I, II, III and IV inhibitors potential dependent A group consisting of sex sodium channel blockers, acetyl
• Group (b) includes nucleic acid synthesis inhibitors (eg, phenylamide fungicides, acylaminomic fungicides), cell division and cytoskeletal inhibitors (eg, MBC fungicides), respiratory inhibitors (eg, QoI fungicides).
• nucleic acid synthesis inhibitors eg, phenylamide fungicides, acylaminomic fungicides
• cell division and cytoskeletal inhibitors eg, MBC fungicides
• respiratory inhibitors eg, QoI fungicides.
• QiI fungicides amino acid synthesis and protein synthesis inhibitors (eg, anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (eg, triazoles and other DMIs) It is a group consisting of fungicides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-action point contact active fungicides, microbial fungicides, and other fungicides. These are described in the classification based on the mechanism of action of FRAC.
• Group (c) is a group of plant growth regulator components (including mycorrhizal fungi and rhizobia).
• Group (d) is a group of repellent components.
• alanical carb + SX means a combination of alanical carb and SX.
• the abbreviation of SX means any one compound of the present invention selected from the compound groups SX1 to SX316 described in Examples.
• all of the following components are known components, and can be obtained from a commercially available preparation or produced by a known method. If this component is a microorganism, it can also be obtained from a fungus depository.
• the numbers in parentheses represent CAS RN (registered trademark).
• Kurstaki strain F810 + SX Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis sub sp. 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. SX, Bacillus thuringiensis subsp. Morrisoni + SX, Bacillus thuringiensis var. Colmeri + SX, Bacillus thuringiensis var.
• the ratio of the compound of the present invention to the present component is not particularly limited, but the weight ratio (compound of the present invention: the present 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 and the like. ..
• Pests include, for example, phytopathogenic microorganisms, harmful arthropods such as harmful insects and 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, Blassoladiomycota, Cytridiomycota, Mucoromycota and Oldiomycota.
• Ascomycota Basidiomycota
• Blassoladiomycota Blassoladiomycota
• Cytridiomycota Cytridiomycota
• Mucoromycota and Oldiomycota.
• the numbers in parentheses indicate the scientific names of the phytopathogenic microorganisms that cause each disease.
• Rice diseases blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellowing dwarf disease (Sclerophthora macrospora), rhizoctonia and Epicoccum nigrum, Trichoderma viride, Rhizopus oryzae; Wheat Diseases: Blumeria graminis, Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, Puccinia striiformis, Puccinia reiformis, Puccinia graminis, ), Monographella nivalis (Microdochium nivale, Microdochium majus), Pyrenophora incarnata, Typhula ishikariensis, Ustilago tritici, Tilletia caries
• Viral disease Big vane disease of lettuce transmitted by Olpidium brassicae, viral disease of various crops transmitted by the genus Polymyxa (eg Polymyxa betae and Polymyxa graminis); Bacterial-induced diseases: Rice seedling bacterial disease (Burkholderia plantarii), cucumber spot bacterial disease (Pseudomonas syringae pv.
• Hakusai soft rot Erwinia carotovora
• potato scab Streptomyces scabiei
• corn Goss's wilt disease Clavibacter michiganensis
• grapes olives, peaches and other piercing diseases
• Xylella fastidiosa apples, peaches, cherry blossoms Root cancer of plants of the family Rosaceae (Agrobacterium tumefaciens).
• harmful arthropods examples include the following.
• Hemiptera Himetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Sejirounka (Sogatella furcifera), Corn unka (Peregrinus maidis), Kitownka (Javesella pellucida), Kitownka (Javesella pellucida)
• Leafhopper (Delphacidae); Leafhopper (Nephotettix cincticeps), Leafhopper (Nephotettix virescens), Leafhopper (Nephotettix nigropictus), Leafhopper (Recilia dorsalis), Leafhopper (Recilia) , Cornleaf Hopper (Dalbulus maidis), Leafhopper (Cofana spectra), Amrasca biguttula biguttula, etc.
• Leafhopper family (Cicadellidae); European spittle bug (Philaenus spumalius), etc.
• Leafhopper (Cercopidae); leafhopper (Aphis fabae), soybean aphid (Aphis glycoines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), leafhopper (Aphis pomi) Myzus persicae), wheat aphid (Brachycaudus helichrysi), leafhopper aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), fake leafhopper aphid (Lipaphis erysimi) Aphididae (Aulacorthum solani), Lettuce aphididae (Nasonovia ribisnigri), Wheat aphididae (Rhopalosiphum padi), Corn aphid (Rhopalosiphum mai
• Lepidoptera Nikameiga (Chilo suppressalis), Dark Hedid Stem Borer (Chilo polychrysus), White Stem Borer (Scirpophaga innotata), Itten Omeiga (Scirpophaga incertulas), Rupela albina, Kobunomeiga (Cnaphalo) Ineha Casino Meiga (Marasmia exigua), Watano Meiga (Notarcha derogata), Awanomeiga (Ostrinia furnacalis), European Corn Borer (Ostrinia nubilalis), Hymadalano Meiga (Hellula undalis), Monki Chronomeiga (Hellula undalis), Monki Chronomeiga (Hellula undalis) , Rice case worm (Nymphula depunctalis), sugar cane bowler (Diatraea saccharalis), egg plant fruit bowler (Leucinodes orbonalis), etc.
• Pieridae Pieris rapae
• Monshirocho Pieris rapae
• Chanokokakumonhamaki Adoxophyes honmai
• Chahamaki Homona magnanima
• Midarekakumonhamaki Archips fuscocupreanus
• Kodling moss Crodia pomonella
• Kansha sinkihamaki Tetramoera schistaceana
• Fruit bowler Citripestis sagittiferella
• European grape wine moss Libesia botrana
• Tortrix moth (Tortricidae); Family (Carposi nidae; Coffee leaf minor (Leucoptera coffeella), Momohamogriga (Lyonetia clerkella), Ginmon Hamogriga (Lyonetia prunifoliella), etc. Lyonetiidae; Lymantriidae (Lymantriidae) such as the genus Euproctis spp.; Plutellidae (Plutellidae) such as Plutella xylostella; ), Gypsy moth (Phthorimaea operculella), Tuta absoluta, etc. (Gelechiidae); Hyphantria cunea, etc.
• Thrips Thysanoptera: Mikankiiro thrips (Frankliniella occidentalis), Minamikiiro thrips (Thrips palmi), Chanokiiro thrips (Scirtothrips dorsalis), Negia thrips (Thrips thrips) , Thripidae such as Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae,
• Agromyzidae such as Agromyzidae (Delia platura), Onion fly (Delia antiqua), Agromyzidae (Pegomya cunicularia); Agromyzidae (Agromyza oryzae), Tomato leafminer (Liriomyza sativae), Agromyzidae (Liriomyza trifolii), Agromyzidae (Chromatomyia horticola), etc.
• Agromyzidae (Agromyzidae); Bactrocera cucurbitae, Mikankomi fly (Bactrocera dorsalis), Nasumi fly (Bactrocera latifurons), Olive mibae (Bactrocera oleae), Quisland mibae (Bactrocera tryoni), Chichukai mibae (Ceratitis mibae) ) Etc.
• Agromyzidae (Tephritidae); Agromyzidae (Hydrellia griseola), Agromyzidae (Hydrellia philippina), Fruitfly (Hydrellia sasakii), etc.
• Agromyzidae (Drosophila melanogaster) and other leafminers (Drosophilidae); Agromyzidae (Megaselia spiracularis) and other leafminers (Phoridae); Agromyzidae (Sciaridae); Agromyzidae (Mayetiola dest) Anopheles mosquitoes (Cecidomyiidae) such as ructor, Aneseolia oryzae; Anophedes mosquitoes (Diopsidae) such as Diopsis macrophthalma; Anopheles mosquitoes (Glossinidae) Anopheles mosquitoes (Simuliidae); Anopheles mosquitoes (Phlebotominae); Anopheles mosquitoes (Tipula aino), Common mosquitoes (Tipula oleracea), European mosquitoes (Tipula paludosa), etc
• Diabrotica spp For example, Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm.
• Western corn root worm (Diabrotica virgifera virgifera)
• Southern corn root worm (Diabrotica undecimpunctata howardi)
• Northern corn root worm Diabrotica barberi
• Mexican corn root worm Mexican corn root worm.
• Diabrotica virgifera zeae (Diabrotica virgifera zeae)), banded cucumber beetle (Diabrotica balteta), cucumber beetle (Diabrotica speciosa) and other bean leaf beetles (Cerotoma trifurcata) (Phyllotreta striolata), cabbage free beetle (Phyllotreta cruciferae), western black free beetle (Phyllotreta pusilla), cabbage stem free beetle (Psylliodes chrysocephala), hop free beetle (Psylliodes chrysocephala), hop free beetle (Psylliodes chrysocephala), hop free beetle (Psylliodes chrysocephala), hop free beetle (Psylliodes chrysocephala), hop free beetle (Psy
• Anthriibidae Japanese beetle (Aponidae) such as Cylas formicarius; Japanese beetle (Bruchidae) such as Brazilian beetle (Zabrotes subfasciatus); Hampei, etc.
• Scolytidae Anomala albopilosa (Euscepes postfasciatus), Alfera postica, Sitophilus zeamais, Japanese beetle (Sitophilus zeamais), Japanese beetle (Sitophilus soryzae), Granaria , Japanese beetle (Lissorhoptrus oryzophilus), Japanese beetle (Rhabdoscelus lineaticollis), Japanese beetle (Anthonomus grandis), Japanese beetle (Sphenophorus venatus) Cane Weeville (Sphenophorus) Levis, Scepticus griseus, Scepticus uniformis, Aracanthus mourei, etc.
• Aracanthus spp. Cotton root beetle (Eutinobothrus brasiliensis), etc. Tribolium castaneum), Red flour beetle (Tribolium consusum), Darkling beetle (Alphitobius diaperinus), etc. Tenebrionidae; Red flour beetle (Rhizopertha dominica), etc.
• Red flour beetle (Trogoderma granarium) and other click beetles (Dermestidae); Tobacco beetle (Lasiod) erma serricorne), drugstore beetle (Stegobium paniceum) and other beetles (Anobiidae); red beetle (Cryptolestes ferrugineus) and other beetles (Laemophloeidae); Sap beetle family (Nitidulidae) such as beetle (Brassicogethes aeneus).
• Orthoptera Orthoptera: Locusta migratoria, Morocco tobibatta (Dociostaurus maroccanus), Australian Tobibatta (Chortoicetes terminifera), Akatobibatta (Nomadacris septemfasciata), Brown Locust (Locustana) Locust (Calliptamus italicus), differential glass hopper (Melanoplus differentialis), two-striped glass hopper (Melanoplus bivittatus), migretry glass hopper (Melanoplus sanguinipes), red legged glass hopper (Melanoplus femurrubrum), clear winged glass hopper (Camn) Sabaquataribatta (Schistocerca gregaria), Yellow wing locust (Gastrimargus musicus), Superslaughted locust (Austracris guttulosa), Kobaneinago (Oxya yezoensis), Hanenagainago (Oxya japon
• Hymenoptera Hymenoptera (Athalia rosae), Japanese ant (Athalia japonica) and other Hymenoptera (Tenthredinidae); Fire ants (Solenopsis invicta), Red imported fire ants (Solenopsis geminata), etc.
• Reef cutting ant (Atta capiguara) and other Hymenoptera (Atta spp.), Fire ant (Acromyrmex spp.), Sashihariari (Paraponera clavata), Luriari (Ochetellus glaber), Fire ant (Monomorium pharaonis), Argentine , Fire ant (Formica japonica), Amime ant (Pristomyrmex punctutus), Fire ant (Pheidole noda), Fire ant (Pheidole megacephala), Fire ant (Camponotus japonicus), Muneakao ant (Camponotus obscuripes) Red imported fire ants (Pogonomyrmex occidentalis) and other ants (Pogonomyrmex spp.), Red imported fire ants (Wasmania auropunctata) and other ants (Wasmania spp.) ), Kebukasuzumebachi (V
• Termites (Blattodea): Termite family (Ectobiidae) such as termites (Blattella germanica); termites (Periplaneta fuliginosa), termites (Periplaneta aamericana), termites (Periplaneta australasiae), termites (periplaneta) Blatta orientalis and other termites (Blattidae); Yamato termites (Reticulitermes speratus), termites (Coptotermes formosanus), American termites (Incisitermes minor), termites (Cryptotermes termites), termites (Cryptotermes termites) Neotermes koshunensis, Satsuma termites (Glyptotermes satsumensis), Nakajima termites (Glyptotermes nakajimai), Catan termites (Glyptotermes fuscus), termites (Hodotermopsis termites) termites (Hodotermopsis termites
• Flea Human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), oriental rat flea (Xenopsylla cheopis), chicken flea (Echidnophaga gallinacea), etc. Hectopsyllidae such as penetrans); Ceratophyllidae such as European cat flea (Nosopsyllus fasciatus).
• Psocodea Primate body lice (Pediculidae) such as head lice (Pediculus humanus capitis); Pubic lice (Pthiridae) such as head lice (Pthirus pubis); Haematopinidae; Bovicoliidae such as Werneckiella spp.; Trichodectes canis, Felicola subrostratus and other pubic lice (Trichodectidae); ), Trinoton spp. And other pubic lice (Menoponidae); Cummingsia spp.
• Thysanura Lepismatidae such as Ctenolepisma villosa and Lepisma saccharina.
• Spiders (Araneae): Cheiracanthium japonicum and other spiders (Eutichuridae); Latrodectus hasseltii and other spiders (Theridiidae).
• Polydesmida Polydesmida (Paradoxosomatidae) such as Polydesmida (Oxidus gracilis) and Nedyopus tambanus.
• Isopoda Armadillidium vulgare and other Armadillidium vulgare.
• Chilopoda Centipede (Scutigeridae) such as Thereuonema hilgendorfi; Scolopendridae (Scolopendra subspinipes); Scolopendridae (Bothropolys rugosus) and others.
• Gastropoda Keelback slugs (Limax marginatus), Keelback slugs (Limax flavus) and other snails (Limacidae); Slugs (Meghimatium bilineatum) and other snails (Philomycidae); Apple snail (Ampullariidae);
• Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus radinus Lenks family (Pratylenchidae); Javanese root-knot nematode (Meloidogyne javanica), Root-knot nematode (Meloidogyne incognita), guava root-knot nematodes (Meloidogyne enterolobii), Root-knot nematode (Meloidogyne) Heteroderidae such as Globodera rostochiensis, Globodera pallida; Hoplara imidae such as Rothelenchulus reniformis; Anguinidae); Tylenchulidae such as Tylenchulus semipenetrans; Longidoridae such as
• Harmful arthropods such as harmful insects and mites, harmful soft animals and harmful nematodes have reduced drug sensitivity to pesticides, acaricides, soft animal agents and nematodes, or are drug resistant. It may be a developed harmful insect, a harmful arthropod such as a harmful mite, a harmful soft-bodied animal, or a harmful nematode.
• the compound or composition A of the present invention is usually mixed with an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier, and if necessary, a surfactant or other pharmaceutical auxiliary agent is added to form an emulsion.
• an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier
• a surfactant or other pharmaceutical auxiliary agent is added to form an emulsion.
• These preparations may be processed and used as mosquito coils, electric mosquito repellent mats, liquid mosquito repellent preparations, fumigants, fumigants, and sheet preparations.
• These formulations usually contain 0.01 to 95% by weight of the compound or composition A of
• Solid carriers used in the formulation include, for example, clays (kaolin clay, diatomaceous earth, bentonite, acidic white clay, etc.), dry silica, wet silica, talc, ceramics, and other inorganic minerals (serisite, quartz, sulfur).
• liquid carrier examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic charcoal.
• alcohols methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.
• ketones acetone, methyl ethyl ketone, cyclohexanone, etc.
• Hydrogens toluene, xylene, ethylbenzene, dodecylbenzene, phenylxysilyl ethane, methylnaphthalene, etc.
• aliphatic hydrocarbons hexane, cyclohexane, kerosene, light oil, etc.
• esters ethyl acetate, butyl acetate, isopropyl myristate, etc.
• nitriles acetritale, isobutyronitrile, etc.
• ethers diisopropyl ether, 1,4-dioxane, 1,2-dimethoxy, etc.
• Ethan diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl
• gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
• surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether and polyethylene glycol fatty acid ester, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates and alkyl sulfates. Examples include ionic surfactants.
• auxiliary agents include fixing agents, dispersants, coloring agents, stabilizers, etc., specifically, for example, casein, gelatin, sugars (temple, arabic gum, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, etc.
• Synthetic water-soluble polymers polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.
• acidic isopropyl phosphate 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol) And 3-tert-butyl-4-methoxyphenol).
• Nimbus registered trademark
• Assist registered trademark
• Aureo registered trademark
• Iharol registered trademark
• Silwet L-77 registered trademark
• BreakThru registered trademark
• SundanceII registered trademark
• Induce® Penetrator®, AgriDex®, Lutensol A8®, NP-7®, Triton®, Nufilm®, Emulgator NP7® ), Emulad (registered trademark), TRITONX45 (registered trademark), AGRAL90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSprayN (registered trademark), BANOLE (registered trademark), etc.
• ARPON registered trademark
• EnSprayN registered trademark
• BANOLE registered trademark
• Examples of the base material of the resin preparation include vinyl chloride-based polymers and polyurethanes, and phthalates (dimethyl phthalate, dioctyl phthalate, etc.) and adipates may be used as necessary for these base materials.
• a plasticizer such as phthalate or phthalate may be added.
• the resin preparation is obtained by kneading a compound in the base material using a normal kneading device and then molding it by injection molding, extrusion molding, press molding or the like, and if necessary, further through steps such as molding and cutting. It can be processed into resin preparations such as plate-shaped, film-shaped, tape-shaped, net-shaped, and string-shaped.
• These resin preparations are processed as, for example, animal collars, animal ear tags, sheet preparations, attracting strings, and horticultural struts.
• the base material of the poison bait include grain flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguairetinic acid, dehydroacetic acid and the like.
• antioxidants such as dibutylhydroxytoluene and nordihydroguairetinic acid, dehydroacetic acid and the like.
• Preservatives, anti-feeding agents for children and pets such as red pepper powder, cheese flavors, onion flavors, pest-attracting flavors such as peanut oil, etc. are added.
• examples of the plant include whole plant, stem and leaf, flower, ear, fruit, trunk, branch, canopy, seed, vegetative reproduction organ and seedling.
• the vegetative reproduction organ means a plant root, stem, leaf, etc. that has the ability to grow when the part is separated from the main body and placed in the soil.
• vegetative reproductive organs include tuberous root, creeping root, bulb, bulb, tuber, rhizome, and stolon. , Rhizophore, cane cuttings, propagule and vine cutting.
• the stolon is sometimes called a runner, and the propagule is also called a pearl bud, which is divided into a granuloma (broad bud) and a scale bud (bulbil).
• Vine means seedlings (collective term for leaves and stems, shoot) of sweet potato, yam, etc.
• Bulbs, corms, tubers, rhizomes, stem fragments, root-bearing bodies or tubers are also collectively referred to as bulbs. Cultivation of potatoes begins by planting tubers in the soil, but the tubers used are commonly referred to as seed potatoes.
• an effective amount of the compound or composition A of the present invention is applied to the soil before or after planting a plant.
• planting hole treatment planting hole spraying, planting hole treatment soil mixing
• stock source treatment stock source spraying, stock source soil mixing, stock source irrigation, seedling raising period latter half stock source treatment
• planting groove Treatment planting ditch, mixing of soil with planting ditch
• streak treatment spraying of streaks, mixing of streaks with soil, spraying of growing season
• Full treatment whole soil spraying, full soil mixing
• side strip treatment water surface treatment (water surface application, after flooding water surface application), other soil spraying treatment (growth season granule foliar spray, under tree canopy or around the main trunk)
• Soil surface spraying, soil surface mixing, sowing hole spraying, ridge surface spraying, inter-strain spraying) and other irrigation treatments
• Examples of the seed treatment include treatment of the compound or composition A of the present invention on seeds or vegetative reproduction organs. Specifically, for example, a suspension of the compound or composition A of the present invention is atomized and the seed surface. Alternatively, a spray treatment of spraying the surface of the vegetative reproduction organ, a smear treatment of applying the compound or composition A of the present invention to the seed or the vegetative reproduction organ, or an immersion treatment of immersing the seed in the chemical solution of the compound or composition A of the present invention for a certain period of time. , A method of coating seeds or vegetative reproduction organs with a carrier containing the compound of the present invention or composition A (film coating treatment, pellet coating treatment, etc.) can be mentioned.
• the above-mentioned vegetative reproduction organs include seed potatoes in particular.
• the composition A can be processed into seeds or vegetative reproduction organs as one preparation, or the composition A is divided into a plurality of different preparations and seeds. Alternatively, it can be processed into vegetative reproduction organs.
• a method of treating the composition A as a plurality of different preparations in a plurality of times for example, a preparation containing only the compound of the present invention as an active ingredient is treated, the seed or the vegetative reproductive organ is air-dried, and then the present ingredient is treated.
• the seed or vegetative reproduction organ holding the compound or composition A of the present invention in the present invention means a state in which the compound or composition A of the present invention is attached to the surface of the seed or vegetative reproduction organ. ..
• the seed or vegetative reproduction organ holding the above-mentioned compound or composition A of the present invention is other than the compound or composition A of the present invention before and after the compound or composition A of the present invention is attached to the seed or vegetative reproduction organ. Materials may be attached.
• the layer comprises one layer or a plurality of layers.
• each layer is a layer containing one or more active ingredients, or is composed of a layer containing one or more active ingredients and a layer not containing the active ingredient.
• the seed or vegetative reproduction organ carrying the compound or composition A of the present invention is obtained, for example, by applying a preparation containing the compound or composition A of the present invention to the seed or vegetative reproduction organ by the above-mentioned seed treatment method. be able to.
• the application rate thereof is usually 1 to 10000 g per 10,000 m 2.
• the amount of the compound of the present invention is usually in the range of 0.001 to 100 g per 1 kg of seeds or vegetative reproduction organs.
• the compound or composition A of the present invention is formulated as an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the concentration of the active ingredient is 0.01 to 10000 ppm, and the granules are applied.
• the agent, powder, etc. are usually applied as they are.
• It can also be treated by wrapping the resin preparation processed into a sheet or string around the crop, stretching it near the crop, or laying it on the soil at the root of the plant.
• the application rate is usually the amount of the compound of the present invention per 1 m 2 of the treated area when treated on a surface.
• the amount is 0.01 to 1000 mg, and when treated in a space, the amount of the compound of the present invention per 1 m 3 of the treatment space is usually 0.01 to 500 mg.
• the compound or composition A of the present invention is formulated as an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the concentration of the active ingredient is 0.1 to 10000 ppm, and applied as an oil preparation. , Aerosol, smoke, poison bait, etc. are applied as they are.
• 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 above plants also include genetically modified crops.
• 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 and Ph represents a phenyl group.
• LCMS compound liquid chromatography / mass spectrometry
• MS mass spectrometry
• Reference manufacturing example 1 Tart at 0 ° C. in a mixture of 19.4 g of methyl 2- (5-bromo-2-methylphenyl) acetate, 14.7 mL of methyl formate, and 150 mL of dimethoxyethane prepared by the method described in WO 2019/016269.
• -Toxipotassium 19.7 g was added, and the mixture was stirred at room temperature for 1 hour.
• 1N Hydrochloric acid was added to the obtained mixture, and the mixture was extracted with MTBE. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure.
• Reference manufacturing example 1-1 Reference The compounds produced according to Production Example 1 and their physical property values are shown below.
• Intermediate 1-2 1 H-NMR (CDCl 3 ) ⁇ : 7.57 (1H, s), 7.38-7.35 (2H, m), 7.29-7.26 (1H, m), 3.87 (3H, s), 3.72 ( 3H, s).
• Equation (M1-a) A compound in which R 1 , R 22 , and R 23 are any combination shown in [Table A1].
• Reference manufacturing example 1-3 Reference The compounds produced according to Production Example 1 and their physical property values are shown below.
• Intermediate 1-4 1 H-NMR (CDCl 3 ) ⁇ : 7.50 (1H, s), 7.37 (1H, dd), 7.28 (1H, d), 6.78 (1H, d), 3.83 (3H, s) , 3.76 (3H, s), 3.69 (3H, s).
• Reference manufacturing example 3 A mixture of 5.0 g of Intermediate 1, bis (triphenylphosphine) palladium (II) dichloride 0.61 g, tributyl (1-ethoxyvinyl) tin 7.0 mL and 1,4-dioxane 30 mL at 100 ° C. for 5 hours. Stirred. 1N Hydrochloric acid was added to the obtained mixture, and the mixture was stirred at room temperature for 30 minutes. The resulting mixture was concentrated under reduced pressure and extracted with ethyl acetate.
• Reference manufacturing example 4-1 The compounds produced according to Reference Production Example 4 and their physical property values are shown below.
• Intermediate 4-2 1 H-NMR (CDCl 3 ) ⁇ : 9.01 (1H, br s), 8.11 (1H, s), 7.59 (1H, s), 7.45 (1H, dd), 7.31 (1H, d) ), 7.23 (1H, d), 3.81 (3H, s), 3.70 (3H, s), 2.19 (3H, s).
• Reference manufacturing example 5 Sodium methoxide (28%) in a mixture of 20.0 g of methyl 2- (5-bromo-2-methylphenyl) acetate, 13.2 mL of isoamyl nitrite and 160 mL of THF prepared by the method described in WO 2019/016269. Methanol solution) 25.4 mL was added, and the mixture was stirred at room temperature for 7 hours. 1N Hydrochloric acid was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure.
• Reference manufacturing example 8 A mixture of 4.5 g of Intermediate 2, 4.0 g of meta-chloroperbenzoic acid, 20 mL of acetonitrile, 20 mL of ethanol, and 20 mL of water was stirred at room temperature for 15 minutes. An aqueous sodium thiosulfate solution and an aqueous sodium hydrogen carbonate solution were added to the obtained mixture, and the mixture was stirred at room temperature for 30 minutes. The resulting mixture was concentrated under reduced pressure and extracted with ethyl acetate. The obtained organic layer was concentrated under reduced pressure to obtain 4.5 g of Intermediate 8 represented by the following formula.
• Production Example 1-1 The compounds produced according to Production Example 1 and their physical property values are shown below.
• Production Example 1-2 The compounds produced according to Production Example 1 and their physical property values are shown below.
• Equation (2a) A compound in which R 7 and L are any combination shown in [Table A9].
• Equation (3a) A compound in which R 1 , R 7 , R 22 , and R 23 are any combination described in [Table A11].
• Production Example 2-1 The compounds produced according to Production Example 2 and their physical property values are shown below.
• Equation (1b) A compound in which R 1 , R 24 , R 25 , R 26 , R 27 , and R 28 are any combination described in [Table A2].
• Compound 2-2 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.70-7.64 (4H, m), 7.62 (1H, s), 7.47 (1H), 7.36-7.32 (2H, m), 3.85 (3H) , S), 3.73 (3H, s), 2.24 (3H, s).
• Compound 2-3 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.61 (1H, s), 7.60-7.56 (2H, m), 7.47-7.39 (3H, m), 7.35-7.29 (3H, m) , 3.84 (3H, s), 3.72 (3H, s), 2.22 (3H, s).
• Equation (1c) A compound in which E is a substituent shown in [Table A3].
• Compound 3-3 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.59 (1H, s), 7.35 (1H, dd), 7.25-7.21 (2H, m), 7.01 (1H, d), 6.85 (1H) , d), 3.84 (3H, s), 3.71 (3H, s), 2.18 (3H, s).
• Compound 3-4 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.60 (1H, s), 7.45 (1H, dd), 7.40-7.39 (1H, m), 7.37-7.34 (3H, m), 7.26 -7.24 (1H, m), 3.84 (3H, s), 3.71 (3H, s), 2.20 (3H, s).
• Production Example 2-2 The compounds that can be produced according to Production Example 2 are shown below.
• R 1 , R 24 , R 25 , R 26 , R 27 , and R 28 are any combination described in [Table A10].
• Production Example 2-3 The compounds produced according to Production Example 2 and their physical property values are shown below.
• R 1 , R 24 , R 25 , R 26 , R 27 , and R 28 are any combination described in [Table A12].
• Compound 2-33 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.60 (1H, s), 7.44-7.36 (2H, m), 7.31-7.26 (2H, m), 6.94-6.85 (2H, m) , 3.84 (3H, s), 3.72 (3H, s), 2.22 (3H, s).
• Compound 2-34 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.60 (1H, s), 7.41-7.30 (2H, m), 7.26-7.24 (1H, m), 7.18-7.12 (1H, m) , 7.03-6.96 (1H, m), 3.85 (3H, s), 3.72 (3H, s), 2.23 (3H, s).
• Compound 2-35 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.60 (1H, s), 7.36-7.27 (2H, m), 7.20 (1H, s), 3.85 (3H, s), 3.72 (3H) , s), 2.25 (3H, s).
• Compound 2-36 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.61 (1H, s), 7.55-7.38 (5H, m), 7.14-7.08 (2H, m), 3.87 (3H, s), 3.74 (3H, s).
• Equation (2b) A compound in which R 24 , R 25 , R 26 , R 27 , and R 28 are any combination described in [Table A13].
• Production Example 3-1 The compounds produced according to Production Example 3 and their physical property values are shown below.
• Equation (1d) A compound in which R 29 , R 30 , R 31 , and R 32 are any combination described in [Table A4].
• Compound 4-2 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.84 (1H, dd), 7.73 (1H, d), 7.61-7.57 (2H, m), 7.49 (1H, d), 7.31 (1H) , d), 7.04 (1H, d), 3.82 (3H, s), 3.70 (3H, s), 2.60 (3H, s), 2.22 (3H, s).
• Production Example 4-1 The compounds produced according to Production Example 4 and their physical property values are shown below.
• Equation (1f) A compound in which R 33 is a substituent shown in [Table A6].
• Compound 6-2 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.74 (1H, d), 7.58 (1H, s), 7.48 (1H, dd), 7.40 (1H, d), 7.24 (1H, s) ), 6.05 (1H, d), 3.83 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 2.05-2.00 (1H, m), 0.98-0.93 (2H, m), 0.80- 0.76 (2H, m).
• Equation (1h) A compound in which R 4 and R 5 are any combination shown in [Table A7].
• Production example 7 A mixture of 0.04 g of sodium hydride (60% oily) and 3 mL of DMF was stirred at 0 ° C. for 30 minutes. To the obtained mixture, 0.25 g of Intermediate 4 was added under ice-cooling, and the mixture was stirred at room temperature for 4 hours. To the resulting mixture was added 0.16 mL of (bromomethyl) cyclobutane at 0 ° C. and stirred at room temperature for 2 hours. A saturated aqueous solution of ammonium chloride was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
• Production Example 7-1 The compounds produced according to Production Example 7 and their physical property values are shown below. A compound in which R 4 and R 5 are any combination shown in [Table A8] among the compounds represented by the formula (1h).
• Production Example 9-1 The compounds produced according to Production Example 9 and their physical property values are shown below.
• Compound 3-9 1 H-NMR (CDCl 3 ) ⁇ : 7.57 (1H, s), 7.29 (1H, dd), 7.18-7.15 (2H, m), 6.12-6.10 (1H, m), 3.81 (3H, s), 3.69 (3H, s), 2.70-2.65 (2H, m), 2.53-2.47 (2H, m), 2.16 (3H, s), 2.02-1.97 (2H, m).
• Compound 11-1 of the present invention represented by the following formula.
• Compound 11-1 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.55 (1H, s), 7.18 (1H, d), 6.99 (1H, dd), 6.87 (1H, d), 3.81 (3H, s) ), 3.69 (3H, s), 3.07 (3H, s), 3.00 (3H, s), 2.14 (3H, s).
• Production Example 10-1 The compounds produced according to Production Example 10 and their physical property values are shown below.
• Compound 11-2 1 H-NMR (CDCl 3 ) ⁇ : 7.55 (1H, s), 7.18 (1H, d), 7.00 (1H, dd), 6.88 (1H, d), 3.81 (3H, s) ), 3.69 (3H, s), 3.46-3.32 (4H, m), 2.14 (3H, s), 1.26-1.15 (6H, m).
• Equation (1A) In the compound represented by (hereinafter referred to as compound (1A)), Q is Q1, R 1 is a methyl group, and R 7 is any substituent selected from the group X (hereinafter, compound). Group SX1).
• Group X Me, Et, Pr, i-Pr, c-Pr, c-Bu, c-Pen, c-Hex, (CH 2 ) 3 CH 3 , CH 2 CH (CH 3 ) 2 , CH (CH 3) ) CH 2 CH 3 , t-Bu, CH 2 c-Pr, (CH 2 ) 4 CH 3 , (CH 2 ) 2 CH (CH 3 ) 2 , CH (CH 3 ) (CH 2 ) 2 CH 3 , CH (CH 2 CH 3 ) CH 2 CH 3 , CH 2 CH (CH 3 ) CH 2 CH 3 , C (CH 3 ) 2 CH 2 CH 3 , CH 2 t-Bu, CH 2 c-Bu, CH 2 c- Pen, (CH 2 ) 2 c-Pr, (1-methylcyclopropyl) methyl, (2-methylcyclopropyl) methyl, 1-cyclopropylethyl, (CH 2 ) 3 c-Pr, (CH 2 ) 5 CH 3
• compound (1A) Q is Q1, R 1 is a chlorine atom, and R 7 is any substituent selected from group X (hereinafter, referred to as compound group SX2).
• Q is Q1, R 1 is a fluorine atom, and R 7 is any substituent selected from group X (hereinafter, referred to as compound group SX3).
• Q is Q1, R 1 is an ethyl group, and R 7 is any substituent selected from group X (hereinafter, referred to as compound group SX4).
• Q is Q1, R 1 is a cyclopropyl group, and R 7 is any substituent selected from group X (hereinafter, referred to as compound group SX5).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, compound wherein R 7 is any of the substituents selected from the group X (hereinafter, the compounds SX6 Note).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, the compound R 7 is any of the substituents selected from the group X (hereinafter, the compounds SX7 Note).
• Q is Q2, L is NH, R 1 is a methyl group, and R 7 is any substituent selected from group X (hereinafter, referred to as compound group SX8). ).
• Q is Q2, L is NH, R 1 is a chlorine atom, the compound R 7 is any of the substituents selected from the group X (hereinafter, referred to as compound group SX9 ).
• Combination A consists of substituent numbers ZA1 to ZA312.
• the substituent numbers ZA1 to ZA312 are the compound (1B), the compound represented by the formula (1D), the compound represented by the formula (1F), the compound represented by the formula (1I), and the compound represented by the formula (1M).
• R X6 compounds represented, compounds of formula (1T), the compound represented by the formula (2C), and R X2, R X3, R X4 , R X5 in the compound represented by the formula (2E), and the combination of R X6 It is represented below, and is hereinafter referred to as [substituent number; R X2 , R X3 , R X4 , R X5 , R X 6 ].
• the substituent number ZA2 is a methyl group
• R X3, R X4, R X5, and R X6 means a combination of a hydrogen atom.
• R 1 is an ethyl group
• R X2 , RX3 , RX4 , RX5 , and RX6 are any of the combinations described in Combination A (hereinafter,).
• Q is Q1
• R 1 is a cyclopropyl group
• R X2, R X3, R X4, R X5, and R X6 is any combination according to the combination A compound ( Hereinafter referred to as compound group SX14).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, one of R X2, R X3, R X4 , R X5, and R X6 are described combination A (Hereinafter referred to as compound group SX15).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, one of R X2, R X3, R X4 , R X5, and R X6 are described combination A (Hereinafter referred to as compound group SX16).
• Q is Q2, L is NH, R 1 is a methyl group, R X2, R X3, R X4, R X5, and R X6 are any according to the combination A Compounds that are a combination (hereinafter referred to as compound group SX17).
• Q is Q2, L is NH, R 1 is a chlorine atom, R X2, R X3, R X4, R X5, and R X6 is either according to the combination A Compounds that are a combination (hereinafter referred to as compound group SX18).
• Q is Q1, R 1 is a chlorine atom, R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter, compound group SX20).
• Q is Q1, R 1 is a fluorine atom, R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter, compound group SX21).
• Q is Q1, R 1 is an ethyl group, R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter, compound group SX22). ).
• Q is Q1, R 1 is a cyclopropyl group, R 4 is a methyl group, and R 5 is any substituent selected from group X (hereinafter, compound group). SX23).
• Q is Q1, R 1 is a methyl group, R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter, compound group SX24).
• Q is Q1, R 1 is a chlorine atom, R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter, compound group SX25). ).
• Q is Q1, R 1 is a fluorine atom, R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter, compound group SX26). ).
• Q is Q1, R 1 is an ethyl group, R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter, compound group SX27).
• Q is Q1, R 1 is a cyclopropyl group, R 4 is an ethyl group, and R 5 is any substituent selected from group X (hereinafter, compound group). SX28).
• Q is Q1, R 1 is a methyl group, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter, compound group SX29). ).
• Q is Q1, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter, compound group SX30). ).
• Q is Q1, R 1 is a fluorine atom, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter, compound group SX31). ).
• Q is Q1, R 1 is an ethyl group, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X (hereinafter, compound group SX32). ).
• Q is Q1, R 1 is a cyclopropyl group, R 4 is a hydrogen atom, and R 5 is any substituent selected from the group X (hereinafter, compound group). SX33).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a methyl group, and R 5 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a methyl group, and R 5 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is an ethyl group, and R 5 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is an ethyl group, and R 5 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X.
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a methyl group, and R 5 is any substituent selected from group X.
• compound group SX40 In compound (1C), Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a methyl group, and R 5 is any substituent selected from group X.
• compound group SX41 In compound (1C), Q is Q2, L is NH, R 1 is a methyl group, R 4 is an ethyl group, and R 5 is any substituent selected from group X. (Hereinafter referred to as compound group SX42).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is an ethyl group, and R 5 is any substituent selected from group X.
• compound group SX43 In compound (1C), Q is Q2, L is NH, R 1 is a methyl group, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X.
• compound group SX44 In compound (1C), Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X. (Hereinafter referred to as compound group SX45).
• Q is Q1
• R 1 is a chlorine atom
• R 4 is a methyl group
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX47).
• Q is Q1, R 1 is a fluorine atom, R 4 is a methyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX48).
• Q is Q1, R 1 is an ethyl group, R 4 is a methyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX49).
• Q is Q1, R 1 is a cyclopropyl group, R 4 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are described in Combination A.
• a compound that is any combination hereinafter referred to as compound group SX50).
• Q is Q1, R 1 is a methyl group, R 4 is an ethyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX51).
• Q is Q1, R 1 is a chlorine atom, R 4 is an ethyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX52).
• Q is Q1, R 1 is a fluorine atom, R 4 is an ethyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX53).
• Q is Q1, R 1 is an ethyl group, R 4 is an ethyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX54).
• Q is Q1, R 1 is a cyclopropyl group, R 4 is an ethyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are described in Combination A.
• a compound that is any combination hereinafter referred to as compound group SX55).
• Q is Q1, R 1 is a methyl group, R 4 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX56).
• Q is Q1, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX57).
• Q is Q1
• R 1 is a fluorine atom
• R 4 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX58).
• R 1 is an ethyl group
• R 4 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of the combinations described in Combination A. (Hereinafter referred to as compound group SX59).
• Q is Q1
• R 1 is a cyclopropyl group
• R 4 is a hydrogen atom
• R X2 , RX3 , RX4 , RX5 , and RX6 are described in Combination A.
• a compound that is any combination hereinafter referred to as compound group SX60).
• Q is Q2
• L is an oxygen atom
• R 1 is a methyl group
• R 4 is a methyl group
• R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX61).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a methyl group, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX62).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is an ethyl group, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX63).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is an ethyl group, R X2, R X3, R X4, R X5, and R X6 Is any combination described in Combination A (hereinafter referred to as compound group SX64).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a hydrogen atom, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX65).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a hydrogen atom, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX66).
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX67).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a methyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX68).
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is an ethyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX69).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is an ethyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX70).
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX71).
• Q is Q2
• L is NH
• R 1 is a chlorine atom
• R 4 is a hydrogen atom
• R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX72).
• the compound that is the group (hereinafter referred to as compound group SX73).
• Q is Q1, R 1 is a chlorine atom, R 4 is a methyl group, and R 8 is any substituent selected from group X (hereinafter, compound group SX74).
• Q is Q1, R 1 is a methyl group, R 4 is a hydrogen atom, and R 8 is any substituent selected from group X (hereinafter, compound group SX75).
• Q is Q1, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R 8 is any substituent selected from group X (hereinafter, compound group SX76). ).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a methyl group, and R 8 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a methyl group, and R 8 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a hydrogen atom, and R 8 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R 8 is any substituent selected from group X.
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a methyl group, and R 8 is any substituent selected from group X. (Hereinafter referred to as compound group SX81).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a methyl group, and R 8 is any substituent selected from group X.
• compound group SX82 In compound (1E), Q is Q2, L is NH, R 1 is a methyl group, R 4 is a hydrogen atom, and R 8 is any substituent selected from group X.
• compound group SX83 In compound (1E), Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R 8 is any substituent selected from group X. (Hereinafter referred to as compound group SX84).
• Q is Q1
• R 1 is a chlorine atom
• R 4 is a methyl group
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX86).
• Q is Q1, R 1 is a methyl group, R 4 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX87).
• Q is Q1, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX88).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a methyl group, R X2, R X3, R X4, R X5, and R X6 Is any combination described in Combination A (hereinafter referred to as compound group SX89).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a methyl group, R X2, R X3, R X4, R X5, and R X6 Is any combination described in Combination A (hereinafter referred to as compound group SX90).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a hydrogen atom, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX91).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a hydrogen atom, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX92).
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX93).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a methyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX94).
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX95).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• Compound Group SX96 A compound that is any combination described in Combination A (hereinafter referred to as Compound Group SX96).
• Equation (1G) In the compound represented by (hereinafter referred to as compound (1G)), Q is Q1, R 1 is a methyl group, and R 6 is any substituent selected from the group Y (hereinafter, compound). Group SX97).
• Group Y Et, Pr, i-Pr, (CH 2 ) 3 CH 3 , CH 2 CH (CH 3 ) 2 , CH (CH 3 ) CH 2 CH 3 , t-Bu, CH 2 c-Pr, (CH) 2 ) 4 CH 3 , (CH 2 ) 2 CH (CH 3 ) 2 , CH (CH 3 ) (CH 2 ) 2 CH 3 , CH (CH 2 CH 3 ) CH 2 CH 3 , CH 2 CH (CH 3 ) CH 2 CH 3 , C (CH 3 ) 2 CH 2 CH 3 , CH 2 t-Bu, CH 2 c-Bu, CH 2 c-Pen, (CH 2 ) 2 c-Pr, (1-methylcyclopropyl) methyl, (2-methylcyclopropyl) methyl, 1-cyclopropylethyl, (CH 2 ) 3 c-Pr, (CH 2 ) 5 CH 3 , (CH 2 ) 3 CH (CH 3 ) 2 , (CH 2 ) 2 CH
• compound (1G) Q is Q1, R 1 is a chlorine atom, and R 6 is any substituent selected from group Y (hereinafter, referred to as compound group SX98).
• compound (1G) Q is Q1, R 1 is a fluorine atom, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX99).
• compound (1G) Q is Q1, R 1 is an ethyl group, and R 6 is any substituent selected from group Y (hereinafter, referred to as compound group SX100).
• Q is Q1, R 1 is a cyclopropyl group, and R 6 is any substituent selected from group Y (hereinafter, referred to as compound group SX101).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 6 is one substituent selected from the group Y (hereinafter, the compounds SX102 Note).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 6 is one substituent selected from the group Y (hereinafter, the compounds SX103 Note).
• Q is Q2, L is NH, R 1 is a methyl group, R 6 is one substituent selected from the group Y (hereinafter, referred to as compound group SX104 ).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 6 is one substituent selected from the group Y (hereinafter, referred to as compound group SX105 ).
• the compound that is the group (hereinafter referred to as compound group SX106).
• Q is Q1, R 1 is a chlorine atom, R 4 is a methyl group, and R 13 is any substituent selected from group X (hereinafter, compound group SX107). ).
• Q is Q1, R 1 is a methyl group, R 4 is a hydrogen atom, and R 13 is any substituent selected from group X (hereinafter, compound group SX108). ).
• Q is Q1, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R 13 is any substituent selected from group X (hereinafter, compound group SX109). ).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a methyl group, and R 13 is any substituent selected from group X.
• compound group SX110 In compound (1H), Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a methyl group, and R 13 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a hydrogen atom, and R 13 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R 13 is any substituent selected from group X.
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a methyl group, and R 13 is any substituent selected from group X. (Hereinafter referred to as compound group SX114).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a methyl group, and R 13 is any substituent selected from group X.
• compound group SX115 In compound (1H), Q is Q2, L is NH, R 1 is a methyl group, R 4 is a hydrogen atom, and R 13 is any substituent selected from group X.
• compound group SX116 In the compound (IH), Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a hydrogen atom, the compound is any of the substituents R 13 are selected from the group X (Hereinafter referred to as compound group SX117).
• Equation (1I) In the compound represented by (hereinafter referred to as compound (1I)), Q is Q1, R 1 is a methyl group, R 4 is a methyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX118).
• Q is Q1
• R 1 is a chlorine atom
• R 4 is a methyl group
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX119).
• Q is Q1, R 1 is a methyl group, R 4 is an ethyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX120).
• Q is Q1, R 1 is a chlorine atom, R 4 is an ethyl group, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX121).
• Q is Q1, R 1 is a methyl group, R 4 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX122).
• Q is Q1, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX123).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a methyl group, R X2, R X3, R X4, R X5, and R X6 Is any combination described in Combination A (hereinafter referred to as compound group SX124).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a methyl group, R X2, R X3, R X4, R X5, and R X6 Is any combination described in Combination A (hereinafter referred to as compound group SX125).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is an ethyl group, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX126).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is an ethyl group, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX127).
• Q is Q2, L is an oxygen atom, R 1 is a methyl group, R 4 is a hydrogen atom, R X2, R X3, R X4, R X5, and R X6 Is any combination described in Combination A (hereinafter referred to as compound group SX128).
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R 4 is a hydrogen atom, R X2, R X3, R X4, R X5, and R X6 Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX129).
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX130).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX131).
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is an ethyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX132).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is an ethyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX133).
• Q is Q2, L is NH, R 1 is a methyl group, R 4 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX134).
• Q is Q2, L is NH, R 1 is a chlorine atom, R 4 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX135).
• Q is Q1
• R 1 is a methyl group
• RX7 , RX8 , and R X9 corresponding to the structure of G and the structure of G.
• R X10 is a compound which is any combination according to the combination B (hereinafter referred to as compound group SX136).
• Combination B comprises substituents ZB1 to ZB1539.
• the substituent numbers ZB1 ⁇ ZB1539 and represents the combination of the substituents R X7, R X8, R X9 and R X10 corresponding to the structure of the structure and G of G in the compound (1 J), hereinafter, [substituent group Number: G, R X7 , R X8 , R X9 , R X10 ].
• the substituent number ZB2 is G1
• R X7 is a methyl group
• R X8, R X9 and R X10 is meant the combination of a hydrogen atom.
• Q is Q1
• R 1 is a chlorine atom
• RX 7 , RX 8 , RX 9 and RX 10 corresponding to the structure of G and the structure of G are any of those described in Combination B.
• Compounds that are a combination (hereinafter referred to as compound group SX137).
• Q is Q1
• R 1 is a fluorine atom
• R X9 and R X10 is one of the described combination B
• Compounds that are a combination hereinafter referred to as compound group SX138).
• Q is Q1
• R 1 is an ethyl group
• R X9 and R X10 is one of the described combination B
• Compounds that are a combination hereinafter referred to as compound group SX139
• Q is Q1
• R 1 is cyclopropyl group
• R X9 and R X10 is described in combination B Compounds that are a combination of (hereinafter referred to as compound group SX140).
• Q is Q2
• L is an oxygen atom
• R 1 is a methyl group
• combination R X7, R X8, R X9 and R X10 corresponding to the structure of the structure and G of G A compound that is any combination described in B (hereinafter referred to as compound group SX141).
• Q is Q2
• L is an oxygen atom
• R 1 is a chlorine atom
• combination R X7, R X8, R X9 and R X10 corresponding to the structure of the structure and G of G A compound that is any combination described in B (hereinafter referred to as compound group SX142).
• Q is Q2
• L is NH
• R 1 is a methyl group
• R X8, R X9 and R X10 is a combination B Compounds that are any combination described in (hereinafter referred to as compound group SX143).
• Q is Q2
• L is NH
• R 1 is a chlorine atom
• R X8, R X9 and R X10 is a combination B Compounds that are any combination described in (hereinafter referred to as compound group SX144).
• Equation (1K) In the compound represented by (hereinafter referred to as compound (1K)), Q is Q1 and R 1 is a methyl group, and R X11 , RX12 , RX13 , RX14 , RX15 , RX16 , RX17. , compound R X18 and R X19 is any combination according to the combination C (hereinafter referred to as compound group SX145).
• Combination C comprises substituents ZC1 to ZC30.
• the substituent numbers ZC1 ⁇ ZC30 represents the combination of R X11, R X12, R X13 , R X14, R X15, R X16, R X17, R X18 and R X19 in the compound (1K), or less, It is described as [substituent number; R X11 , R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 , R X19 ].
• R X11 is a methyl group
• R X12, R X13, R X14, R X15, R X16, R X17, R X18 and R X19 is meant the combination of a hydrogen atom.
• Q is Q1
• R 1 is a chlorine atom
• a R X11, R X12, R X13 , R X14, R X15, R X16, R X17, R X18 and R X19 is a combination C
• a compound that is any combination of the above hereinafter referred to as compound group SX146).
• Q is Q2
• L is an oxygen atom
• R 1 is a methyl group
• compound R X19 is any combination according to the combination C (hereinafter referred to as compound group SX147).
• Q is Q2
• L is an oxygen atom
• R 1 is a chlorine atom
• R X11, R X12, R X13, R X14, R X15, R X16, R X17, R X18 and compound R X19 is any combination according to the combination C (hereinafter referred to as compound group SX148).
• Q is Q2, L is NH
• R 1 is a methyl group
• Q is Q2
• L is NH
• R 1 is a chlorine atom
• Equation (1L) In the compound represented by (hereinafter referred to as compound (1L)), Q is Q1 and R 1 is a methyl group, and R X11 , RX12 , RX13 , RX14 , RX15 , RX16 and RX17. Is any combination described in Combination E (hereinafter referred to as compound group SX151).
• Combination E comprises substituents ZE1 to ZE20.
• the substituent numbers ZE1 ⁇ ZE20 represents the combination of R X11, R X12, R X13 , R X14, R X15, R X16 and R X17 in the compound (1L), below, Substituent group number; R X11 , R X12 , R X13 , R X14 , R X15 , R X16 , R X17 ].
• R X11 is a methyl group
• R X12, R X13, R X14, R X15, R X16 and R X17 is meant the combination of a hydrogen atom.
• Q is Q2, L is an oxygen atom, R 1 is a chlorine atom, R X11, R X12, R X13, R X14, R X15, R X16 and R X17 is a combination E
• compound group SX154 Compounds that are any combination described in (hereinafter referred to as compound group SX154).
• Q is Q2, L is NH, R 1 is a methyl group, and R X11 , RX12 , RX13 , RX14 , RX15 , RX16 and RX17 are in combination E.
• a compound that is any combination of the above hereinafter referred to as compound group SX155).
• Q is Q2
• L is NH
• R 1 is a chlorine atom
• R X11 , RX12 , RX13 , RX14 , RX15 , RX16 and RX17 are in combination E.
• a compound that is any combination of the above hereinafter referred to as compound group SX156).
• Equation (1M) In the compound represented by (hereinafter referred to as compound (1M)), R 1 is a methyl group, R X 8 is a hydrogen atom , R X 9 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R. X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX157).
• compound (1M) R 1 is a methyl group
• RX 8 is a methyl group
• RX 9 is a hydrogen atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX158).
• compound (1M) R 1 is a methyl group
• RX 8 is a hydrogen atom
• RX 9 is a methyl group
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• compound group SX159 A compound that is a combination of any of the above (hereinafter referred to as compound group SX159).
• R 1 is a methyl group
• R X 8 is a fluorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX160).
• R 1 is a methyl group
• RX 8 is a hydrogen atom
• RX 9 is a fluorine atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX161).
• compound (1M) R 1 is a methyl group, R X 8 is a chlorine atom , R X 9 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• compound group SX162 A compound that is a combination of any of the above (hereinafter referred to as compound group SX162).
• R 1 is a methyl group
• RX 8 is a hydrogen atom
• RX 9 is a chlorine atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX163).
• compound (1M) R 1 is a chlorine atom
• R X 8 is a hydrogen atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• compound group SX164 A compound that is a combination of any of the above (hereinafter referred to as compound group SX164).
• R 1 is a chlorine atom
• R X 8 is a methyl group
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX165).
• R 1 is a chlorine atom
• RX 8 is a hydrogen atom
• RX 9 is a methyl group
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX166).
• R 1 is a chlorine atom
• R X 8 is a fluorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX167).
• R 1 is a chlorine atom
• R X 8 is a hydrogen atom
• R X 9 is a fluorine atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX168).
• compound (1M) R 1 is a chlorine atom, R X 8 is a chlorine atom , R X 9 is a hydrogen atom, and RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• compound group SX169 A compound that is a combination of any of the above (hereinafter referred to as compound group SX169).
• R 1 is a chlorine atom
• R X 8 is a hydrogen atom
• R X 9 is a chlorine atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• compound group SX170 A compound that is a combination of any of the above (hereinafter referred to as compound group SX170).
• R 1 is a chlorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any combination described in Combination A.
• compound group SX173 In compound (1N), R 1 is a chlorine atom
• R X 9 is a methyl group
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of the combinations described in Combination A. (Hereinafter referred to as compound group SX174).
• Equation (1O) In the compound represented by (hereinafter referred to as compound (1O)), R 1 is a methyl group, R X 8 is a hydrogen atom , R X 9 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R. X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX175).
• R 1 is a methyl group
• R X 8 is a fluorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX176).
• compound (1O) R 1 is a methyl group
• R X 8 is a chlorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• compound group SX177 A compound that is a combination of any of the above (hereinafter referred to as compound group SX177).
• R 1 is a methyl group
• RX 8 is a methyl group
• RX 9 is a hydrogen atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX178).
• compound (1O) R 1 is a chlorine atom
• R X 8 is a hydrogen atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• compound group SX179 A compound that is a combination of any of the above (hereinafter referred to as compound group SX179).
• R 1 is a chlorine atom
• R X 8 is a fluorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX180).
• R 1 is a chlorine atom
• R X 8 is a chlorine atom
• R X 9 is a hydrogen atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX181).
• compound (1O) R 1 is a chlorine atom
• R X 8 is a methyl group
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• compound group SX182 A compound that is a combination of any of the above (hereinafter referred to as compound group SX182).
• Equation (1P) In the compound represented by (hereinafter referred to as compound (1P)), R 1 is a methyl group, R X 7 is a hydrogen atom , R X 9 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R. X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX183).
• R 1 is a methyl group
• R X 7 is a fluorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX184).
• R 1 is a methyl group
• R X 7 is a chlorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX185).
• R 1 is a methyl group
• RX 7 is a hydrogen atom
• RX 9 is a fluorine atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX186).
• R 1 is a chlorine atom
• R X 7 is a hydrogen atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX187).
• compound (1P) R 1 is a chlorine atom
• R X 7 is a fluorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• compound group SX188 A compound that is a combination of any of the above (hereinafter referred to as compound group SX188).
• R 1 is a chlorine atom
• R X 7 is a chlorine atom
• R X 9 is a hydrogen atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX189).
• R 1 is a chlorine atom
• R X 7 is a hydrogen atom
• R X 9 is a fluorine atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are described in Combination A.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX190).
• Equation (1Q) In the compound represented by (hereinafter referred to as compound (1Q)), R 1 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are any combination described in Combination A.
• a compound hereinafter referred to as compound group SX191).
• R 1 is a chlorine atom
• R X2, R X3, R X4, R X5, and compound R X6 is any combination according to the combination A (hereinafter, referred to as compound group SX192 ).
• Equation (1R) In the compound represented by (hereinafter referred to as compound (1R)), R 1 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are any combination described in Combination A. A compound (hereinafter referred to as compound group SX193). In the compound (1R), R 1 is a chlorine atom, R X2, R X3, R X4, R X5, and compound R X6 is any combination according to the combination A (hereinafter, referred to as compound group SX194 ).
• Equation (1S) In the compound represented by (hereinafter referred to as compound (1S)), R 1 is a methyl group, RX 7 is a hydrogen atom, and RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are combined A. Compounds that are any combination described in (hereinafter referred to as compound group SX195). In compound (1S), R 1 is a chlorine atom, R X 7 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any combination described in Combination A. (Hereinafter referred to as compound group SX196).
• R 1 is a methyl group
• RX 7 is a fluorine atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are any of the combinations described in Combination A.
• compound group SX197 In compound (1S), R 1 is a chlorine atom
• R X 7 is a fluorine atom
• R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any combination described in Combination A. (Hereinafter referred to as compound group SX198).
• Equation (1T) In the compound represented by (hereinafter referred to as compound (1T)), R 1 is a methyl group, RX 7 is a hydrogen atom, and RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are combined A. Compounds that are any combination described in (hereinafter referred to as compound group SX199). In compound (1T), R 1 is a chlorine atom, R X 7 is a hydrogen atom, and R X 2 , R X 3 , R X 4 , R X 5 , and R X 6 are any of the combinations described in Combination A. (Hereinafter referred to as compound group SX200).
• R 1 is a methyl group
• RX 7 is a fluorine atom
• RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are any of the combinations described in Combination A.
• compound group SX201 In compound (1T), R 1 is a chlorine atom, RX 7 is a fluorine atom, and RX 2 , RX 3 , RX 4 , RX 5 , and RX 6 are any of the combinations described in Combination A. (Hereinafter referred to as compound group SX202).
• R 1 is a methyl group
• R X 8 is a hydrogen atom
• R X 9 is a hydrogen atom, which corresponds to the structure of A and the structure of A.
• substituents R X11, R X12, R X13 and R X14 is any combination according to the combination D compound (hereinafter referred to as compound group SX203).
• Combination D consists of substituent numbers ZD1 to ZD334.
• Substituent numbers ZD1 to ZD334 are compound (1U), compound represented by formula (1V), compound represented by formula (1W), compound represented by formula (1X), compound represented by formula (1Y), and the like.
• compounds of formula (1Z) and is intended to represent a combination of the formula substituents correspond to the structure of the structure and a of a in the compound represented by (2A) R X11, R X12 , R X13 and R X14, Hereinafter, it is described as [substituent number; A, R X11 , R X12 , R X13 , R X 14 ].
• the substituent number ZD2 means a combination in which A is AA1, R X11 is a methyl group, and R X12 , R X13 and R X 14 are hydrogen atoms.
• R 1 is a methyl group
• R X8 is a fluorine atom
• a R X9 is a hydrogen atom
• a substituent corresponding to the structure of the structure and
• a A R X11, R X12, R X13 and compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX204).
• R 1 is a methyl group
• R X8 is a hydrogen atom
• R X9 is a fluorine atom
• a substituent corresponding to the structure of the structure and
• a A R X11, R X12, R X13 and compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX205).
• R 1 is a chlorine atom
• R X8 is a hydrogen atom
• an R X9 is a hydrogen atom
• a substituent corresponding to the structure of the structure and A A R X11, R X12, R X13 And R X 14 are any of the combinations described in Combination D (hereinafter referred to as Compound Group SX206).
• R 1 is a chlorine atom
• R X 8 is a fluorine atom
• R X 9 is a hydrogen atom
• the substituents RX 11 , RX 12 , and RX 13 corresponding to the structure of A and the structure of A.
• compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX207).
• R 1 is a chlorine atom
• R X 8 is a hydrogen atom
• R X 9 is a fluorine atom
• the substituents RX 11 , RX 12 , and RX 13 corresponding to the structure of A and the structure of A.
• compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX208).
• R 1 is a methyl group
• R X 9 is a hydrogen atom
• the substituents R X11 , RX12 , corresponding to the structure of A and the structure of A, compound R X13 and R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX209).
• R 1 is a methyl group
• R X 9 is a methyl group
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in Combination D.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX210).
• R 1 is a chlorine atom
• R X 9 is a hydrogen atom
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in Combination D.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX211).
• R 1 is a chlorine atom
• R X 9 is a methyl group
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in Combination D.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX212).
• R 1 is a methyl group
• R X 8 is a hydrogen atom
• R X 9 is a hydrogen atom, which corresponds to the structure of A and the structure of A.
• substituents R X11, R X12, R X13 and R X14 is any combination according to the combination D compound (hereinafter referred to as compound group SX213).
• R 1 is a methyl group
• R X8 is a fluorine atom
• a R X9 is a hydrogen atom
• a substituent corresponding to the structure of the structure and
• a A R X11, R X12, R X13 and compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX214).
• R 1 is a methyl group
• R X8 is a chlorine atom
• a R X9 is a hydrogen atom
• a substituent corresponding to the structure of the structure and
• a A R X11, R X12, R X13 and compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX215).
• R 1 is a methyl group
• R X8 is a methyl group
• an R X9 is a hydrogen atom, a substituent corresponding to the structure of the structure
• a A R X11, R X12, R X13 And R X 14 are any of the combinations described in Combination D (hereinafter referred to as Compound Group SX216).
• R 1 is a chlorine atom
• R X8 is a hydrogen atom
• an R X9 is a hydrogen atom
• a substituent corresponding to the structure of the structure and A A R X11, R X12, R X13 And R X 14 are any of the combinations described in Combination D (hereinafter referred to as Compound Group SX217).
• R 1 is a chlorine atom
• R X 8 is a fluorine atom
• R X 9 is a hydrogen atom
• the substituents RX 11 , RX 12 , and RX 13 corresponding to the structure of A and the structure of A.
• compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX218).
• R 1 is a chlorine atom
• R X 8 is a chlorine atom
• R X 9 is a hydrogen atom
• compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX219).
• R 1 is a chlorine atom
• R X8 is a methyl group
• an R X9 is a hydrogen atom
• a substituent corresponding to the structure of the structure and
• a A R X11, R X12, R X13 and compound R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX220).
• R 1 is a methyl group, a substituent corresponding to the structure of the structure and A
• R X11, R X12, R X13 and R X14 is a combination D
• compound group SX221 Compounds that are any combination described in (hereinafter referred to as compound group SX221).
• R 1 is a chlorine atom
• the substituents R X11 , RX12 , RX13 and RX14 corresponding to the structure of A and the structure of A are any combination described in Combination D. (Hereinafter referred to as compound group SX222).
• R 1 is a methyl group, a substituent corresponding to the structure of the structure and A
• a R X11, R X12, R X13 and R X14 is a combination D
• Compounds that are any combination described in hereinafter referred to as compound group SX223).
• compound (1Y) a compound in which R 1 is a chlorine atom and the substituents R X11 , RX12 , RX13 and RX14 corresponding to the structure of A and the structure of A are any combination described in combination D. (Hereinafter referred to as compound group SX224).
• R 1 is a methyl group
• R X 7 is a hydrogen atom
• the substituents R X11 , RX12 , corresponding to the structure of A and the structure of A, compound R X13 and R X14 is any combination according to the combination D (hereinafter, referred to as compound group SX225).
• R 1 is a chlorine atom
• R X 7 is a hydrogen atom
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in Combination D.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX226).
• R 1 is a methyl group
• R X 7 is a fluorine atom
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in Combination D.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX227).
• R 1 is a chlorine atom
• R X 7 is a fluorine atom
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in Combination D.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX228).
• Equation (2A) [In the formula, A represents any of the groups represented by formulas AA1 to AA4. ]
• R 1 is a methyl group
• R X 7 is a hydrogen atom
• the substituents R X11 , RX12 corresponding to the structure of A and the structure of A
• a compound in which R X13 and R X 14 are any combination described in Combination D hereinafter referred to as compound group SX229).
• R 1 is a chlorine atom
• R X 7 is a hydrogen atom
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in Combination D.
• a compound that is a combination of any of the above hereinafter referred to as compound group SX230).
• R 1 is a methyl group
• R X 7 is a fluorine atom
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in Combination D.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX231).
• R 1 is a chlorine atom
• R X 7 is a fluorine atom
• the substituents R X 11 , R X 12 , R X 13 and R X 14 corresponding to the structure of A and the structure of A are described in combination D.
• a compound that is a combination of any of the above (hereinafter referred to as compound group SX232).
• the compound that is the group hereinafter referred to as compound group SX233).
• Q is Q1, R 22 is a hydrogen atom, R 23 is a methyl group, and R 7 is any substituent selected from group X (hereinafter, compound group SX234).
• Q is Q1, R 22 is a chlorine atom, R 23 is a hydrogen atom, and R 7 is any substituent selected from group X (hereinafter, compound group SX235).
• compound (2B) Q is Q1, R 22 is a hydrogen atom, R 23 is a chlorine atom, and R 7 is any substituent selected from group X (hereinafter, compound group SX236). ).
• Q is Q2, L is an oxygen atom, R 22 is a methyl group, R 23 is a hydrogen atom, and R 7 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a methyl group, and R 7 is any substituent selected from group X.
• Equation (2C) In the compound represented by (hereinafter referred to as compound (2C)), Q is Q1, R 22 is a methyl group, R 23 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX245).
• Q is Q1
• R 22 is a hydrogen atom
• R 23 is a methyl group
• R X2 , RX3 , RX4 , RX5 , and RX6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX246).
• compound (2C) Q is Q1, R 22 is a chlorine atom, R 23 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX247).
• Q is Q1, R 22 is a hydrogen atom, R 23 is a chlorine atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are any of those described in Combination A.
• a compound that is a combination of the above hereinafter referred to as compound group SX248).
• Q is Q2, L is an oxygen atom, R 22 is a methyl group, R 23 is a hydrogen atom, R X2 , R X3 , R X4 , R X5 , and R X6. Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX249).
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6. Is any combination described in Combination A (hereinafter referred to as compound group SX250).
• Q is Q2, L is an oxygen atom, R 22 is a chlorine atom, R 23 is a hydrogen atom, R X2 , R X3 , R X4 , R X5 , and R X6. Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX251).
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a chlorine atom, R X2 , R X3 , R X4 , R X5 , and R X6. Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX252).
• Q is Q2, L is an oxygen atom, R 22 is a methyl group, R 23 is a hydrogen atom, R X2 , R X3 , R X4 , R X5 , and R X6. Is any of the combinations described in Combination A (hereinafter referred to as Compound Group SX253).
• Q is Q2, L is NH, R 22 is a hydrogen atom, R 23 is a methyl group, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as Compound Group SX254).
• Q is Q2, L is NH, R 22 is a chlorine atom, R 23 is a hydrogen atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as compound group SX255).
• Q is Q2, L is NH, R 22 is a hydrogen atom, R 23 is a chlorine atom, and R X2 , RX3 , RX4 , RX5 , and RX6 are.
• a compound that is any combination described in Combination A hereinafter referred to as compound group SX256).
• Equation (2D) In the compound represented by (hereinafter referred to as compound (2D)), Q is Q1, R 22 is a methyl group, R 23 is a hydrogen atom, R 4 is a methyl group, and R 5 is a group.
• a compound that is any substituent selected from X hereinafter referred to as compound group SX257).
• Q is Q1
• R 22 is a hydrogen atom
• R 23 is a methyl group
• R 4 is a methyl group
• R 5 is any substituent selected from group X.
• Q is Q1
• R 22 is a chlorine atom
• R 23 is a hydrogen atom
• R 4 is a methyl group
• R 5 is any substituent selected from group X.
• a compound hereinafter referred to as compound group SX259).
• Q is Q1
• R 22 is a hydrogen atom
• R 23 is a chlorine atom
• R 4 is a methyl group
• R 5 is any substituent selected from group X.
• Q is Q2, L is an oxygen atom
• R 22 is a methyl group
• R 23 is a hydrogen atom
• R 4 is a methyl group
• R 5 is selected from group X.
• a compound that is one of the substituents (hereinafter referred to as compound group SX261).
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a methyl group, R 4 is a methyl group, and R 5 is selected from group X.
• a compound that is one of the substituents (hereinafter referred to as compound group SX262).
• Q is Q2, L is an oxygen atom, R 22 is a chlorine atom, R 23 is a hydrogen atom, R 4 is a methyl group, and R 5 is selected from group X.
• a compound that is one of the substituents (hereinafter referred to as compound group SX263).
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a chlorine atom, R 4 is a methyl group, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX264).
• Q is Q2, L is NH, R 22 is a methyl group, R 23 is a hydrogen atom, R 4 is a methyl group, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX265).
• Q is Q2, L is NH, R 22 is a hydrogen atom, R 23 is a methyl group, R 4 is a methyl group, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX266).
• Q is Q2, L is NH, R 22 is a chlorine atom, R 23 is a hydrogen atom, R 4 is a methyl group, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX267).
• Q is Q2, L is NH, R 22 is a hydrogen atom, R 23 is a chlorine atom, R 4 is a methyl group, and R 5 is selected from group X.
• a compound that is one of the substituents (hereinafter referred to as compound group SX268).
• Q is Q1, R 22 is a methyl group, R 23 is a hydrogen atom, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X.
• a compound hereinafter referred to as compound group SX269).
• Q is Q1, R 22 is a hydrogen atom, R 23 is a methyl group, R 4 is a hydrogen atom, and R 5 is any substituent selected from group X.
• a compound (hereinafter referred to as compound group SX270).
• Q is Q1
• R 22 is a chlorine atom
• R 23 is a hydrogen atom
• R 4 is a hydrogen atom
• R 5 is any substituent selected from group X.
• a compound hereinafter referred to as compound group SX271.
• Q is Q1
• R 22 is a hydrogen atom
• R 23 is a chlorine atom
• R 4 is a hydrogen atom
• R 5 is any of the substituents selected from group X.
• a compound hereinafter referred to as compound group SX272).
• compound (2D) Q is Q2, L is an oxygen atom, R 22 is a methyl group, R 23 is a hydrogen atom, R 4 is a hydrogen atom, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX273.
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a methyl group, R 4 is a hydrogen atom, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX274.
• Q is Q2, L is an oxygen atom, R 22 is a chlorine atom, R 23 is a hydrogen atom, R 4 is a hydrogen atom, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX275).
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a chlorine atom, R 4 is a hydrogen atom, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX276).
• Q is Q2, L is NH, R 22 is a methyl group, R 23 is a hydrogen atom, R 4 is a hydrogen atom, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX277).
• Q is Q2, L is NH, R 22 is a hydrogen atom, R 23 is a methyl group, R 4 is a hydrogen atom, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX278).
• Q is Q2, L is NH, R 22 is a chlorine atom, R 23 is a hydrogen atom, R 4 is a hydrogen atom, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX279).
• Q is Q2, L is NH, R 22 is a hydrogen atom, R 23 is a chlorine atom, R 4 is a hydrogen atom, and R 5 is selected from group X.
• a compound that is one of the substituents hereinafter referred to as compound group SX280).
• Equation (2E) In the compound represented by (hereinafter referred to as compound (2E)), Q is Q1, R 22 is a methyl group, R 23 is a hydrogen atom, R 4 is a methyl group, and R X 2 and R A compound in which X3 , R X4 , R X5 , and R X 6 are any combination described in Combination A (hereinafter referred to as compound group SX281).
• Q is Q1
• R 22 is a hydrogen atom
• R 23 is a methyl group
• R 4 is a methyl group
• R X2 , R X3 , R X4 , R X5 , and R
• a compound in which X6 is any combination described in Combination A (hereinafter referred to as compound group SX282).
• R 22 is a chlorine atom
• Q is Q1
• R 23 is a hydrogen atom
• R 4 is a methyl group
• a compound in which X6 is any combination described in Combination A (hereinafter referred to as compound group SX283).
• R 22 is a hydrogen atom
• Q is Q1
• R 23 is a chlorine atom
• R 4 is a methyl group, R X2 , R X3 , R X4 , R X5 , and R.
• a compound in which X6 is any combination described in Combination A (hereinafter referred to as compound group SX284).
• Q is Q1
• R 22 is a methyl group
• R 23 is a hydrogen atom
• R 4 is a hydrogen atom
• a compound in which X6 is any combination described in Combination A (hereinafter referred to as compound group SX285).
• Q is Q1
• R 22 is a hydrogen atom
• R 23 is a methyl group
• R 4 is a hydrogen atom, R X2 , R X3 , R X4 , R X5 , and R.
• a compound in which X6 is any combination described in Combination A (hereinafter referred to as compound group SX286).
• Q is Q1
• R 22 is a chlorine atom
• R 23 is a hydrogen atom
• R 4 is a hydrogen atom
• a compound in which X6 is any combination described in Combination A (hereinafter referred to as compound group SX287).
• Q is Q1
• R 22 is a hydrogen atom
• R 23 is a chlorine atom
• R 4 is a hydrogen atom, R X2 , R X3 , R X4 , R X5 , and R.
• a compound in which X6 is any combination described in Combination A (hereinafter referred to as compound group SX288).
• Q is Q2
• L is an oxygen atom
• R 22 is a methyl group
• R 23 is a hydrogen atom
• R 4 is a methyl group
• R X2 , R X3 , R. X4, R X5 is any combination according to the combination a (hereinafter, referred to as compound group SX289).
• Q is Q2
• L is an oxygen atom
• R 22 is a hydrogen atom
• R 23 is a methyl group
• R 4 is a methyl group
• R X4, R X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX290).
• R 22 is a chlorine atom
• Q is Q2
• L is an oxygen atom
• R 23 is a hydrogen atom
• R 4 is a methyl group
• R X2 , R X3 , R. X4, R X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX291).
• R 22 is a hydrogen atom
• Q is Q2
• L is an oxygen atom
• R 23 is a chlorine atom
• R 4 is a methyl group
• R X2 , R X3 , R X4, R X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX292).
• Q is Q2
• L is an oxygen atom
• R 22 is a methyl group
• R 23 is a hydrogen atom
• R 4 is a hydrogen atom
• R X2 , R X3 , R. X4, R X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX293).
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a methyl group, R 4 is a hydrogen atom, and R X2 , R X3 , R. X4, R X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX294).
• Q is Q2, L is an oxygen atom, R 22 is a chlorine atom, R 23 is a hydrogen atom, R 4 is a hydrogen atom, and R X2 , R X3 , and R.
• R X4, R X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX295).
• Q is Q2, L is an oxygen atom, R 22 is a hydrogen atom, R 23 is a chlorine atom, R 4 is a hydrogen atom, and R X2 , R X3 , and R.
• X4, R X5, and compound R X6 is any combination according to the combination a (hereinafter, referred to as compound group SX296).
• Q is Q2, L is NH, R 22 is a methyl group, R 23 is a hydrogen atom, R 4 is a methyl group, R X2 , R X3 , R X4.
• R X5 , and R X 6 are any combination described in Combination A (hereinafter referred to as compound group SX297).
• Q is Q2
• L is NH
• R 22 is a hydrogen atom
• R 23 is a methyl group
• R 4 is a methyl group
• R X5 , and R X 6 are any combination described in Combination A (hereinafter referred to as compound group SX298).
• R 22 is a chlorine atom
• Q is Q2
• L is NH
• R 23 is a hydrogen atom
• R 4 is a methyl group
• R 22 is a hydrogen atom
• Q is Q2
• L is NH
• R 23 is a chlorine atom
• R 4 is a methyl group
• R X5 , and R X 6 are any combination described in Combination A (hereinafter referred to as compound group SX300).
• Q is Q2
• L is NH
• R 22 is a methyl group
• R 23 is a hydrogen atom
• R 4 is a hydrogen atom
• R X5 , and R X 6 are any combination described in Combination A (hereinafter referred to as compound group SX301).
• Q is Q2, L is NH, R 22 is a hydrogen atom, R 23 is a methyl group, R 4 is a hydrogen atom, and R X2 , R X3 , and R X4. , R X5 , and R X 6 are any combination described in Combination A (hereinafter referred to as compound group SX302).
• Q is Q2, L is NH, R 22 is a chlorine atom, R 23 is a hydrogen atom, R 4 is a hydrogen atom, and R X2 , R X3 , and R X4.
• R X5 , and R X 6 are any combination described in Combination A (hereinafter referred to as compound group SX303).
• Q is Q2
• L is NH
• R 22 is a hydrogen atom
• R 23 is a chlorine atom
• R 4 is a hydrogen atom
• R X5 , and R X 6 are any combination described in Combination A (hereinafter referred to as compound group SX304).
• the compound that is the group (hereinafter referred to as compound group SX305).
• Q is Q1, R 22 is a chlorine atom, R 23 is a hydrogen atom, and R 6 is any substituent selected from group Y (hereinafter, compound group SX306). ).
• Q is Q1, R 22 is a hydrogen atom, R 23 is a methyl group, and R 6 is any substituent selected from group Y (hereinafter, compound group SX307). ).
• compound (2F) Q is Q1, R 22 is a hydrogen atom, R 23 is a chlorine atom, and R 6 is any substituent selected from group Y (hereinafter, compound group SX308). ).
• Q is Q2, L is an oxygen atom, R 22 is a methyl group, R 23 is a hydrogen atom, and R 6 is any substituent selected from group Y.
• Q is Q2, L is an oxygen atom, R 22 is a chlorine atom, R 23 is a hydrogen atom, and R 6 is any substituent selected from group Y.
• the compound S of the present invention represents the compounds described in the compound groups SX1 to SX316.
• a pharmaceutical product is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds S of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic silicon hydroxide.
• composition 2 20 parts of any one of the compounds S of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, finely pulverized by a wet pulverization method, and then contained therein. 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and mixed by stirring to obtain a preparation.
• a pharmaceutical product is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compounds S of the present invention, 88 parts of kaolin clay and 10 parts of talc.
• composition is obtained by thoroughly mixing 5 parts of any one of the compounds S of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
• composition 20 parts of any one of the compounds S of the present invention; 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water are mixed to make a total of 100 parts, and a crusher is used. The preparation is obtained by processing.
• Test Examples 1 to 8 is a test group performed under the same conditions as described in each Test Example except that DMSO is dispensed in place of the DMSO diluent containing the compound of the present invention. Represents. Further, "no treatment" in Test Examples 9 to 20 means that the aqueous diluted solution of the preparation containing the compound of the present invention was not sprayed.
• the untreated group in Test Example 21 and Test Example 25 means a group that operates in the same manner as the treated group except that the test compound is not used.
• Test Example 1 Control test against Zymoseptoria tritici Compound 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 2-1, 2-2, 2 of the present invention -3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-15 , 2-16, 2-17, 2-18, 2-19, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3 -9, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 4-7, 4-8, 5-1, 5-2, 5-3, 5-4 , 5-5, 5-7, 5-8, 5-10, 5-11, 5-12, 5-13, 5-14, 5-15, 5-16, 5-18, 5-19, 6 -1, 6-2, 6-3, 6-5, 6-6, 6-7, 6-8, 7-1, 8-1, 8-2, 8-3, 8-4, 8-5 , 8-6, 8-7, 9-1, 9-2, 9-3,
• Test Example 2 Control test against Phytophthora capsici Compounds of the present invention 1-2, 1-3, 2-6, 2-11, 3-1, 3-4, 6-3, 8-4, Dilute 8-12, 8-21, 9-1, or 10-5 with DMSO so as to contain 150 ppm, dispense 1 ⁇ L into a titer plate (96 wells), and inoculate spores of Phytophthora phytophthora in advance. 150 ⁇ L of the liquid medium for decoction of potato decoction (PDB medium) was dispensed. This plate was cultured at 27 ° C.
• PDB medium potato decoction
• the growth rate in each group treated with the compound of the present invention was 50% or less of the growth rate in the untreated group.
• Test Example 3 Control test against Pythium ultimum Compounds of the present invention 1-2, 1-3, 2-3, 2-7, 2-8, 2-9, 2-10, 2-13, 2 -15, 2-17, 3-1, 3-4, 6-3, 8-1, 8-4, 9-1, 1-1, 2-25, 2-26, 2-33, 8-9 , 8-11, 8-12, 8-14, 8-17, 8-18, or 10-5 diluted with DMSO to contain 150 ppm, dispensed in 1 ⁇ L into a titer plate (96 wells), and then preliminarily 150 ⁇ L of a potato decoction liquid medium (PDB medium) inoculated with spores of seedling blight was dispensed.
• PDB medium potato decoction liquid medium
• the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of the seedling blight bacterium.
• the growth rate in each group treated with the compound of the present invention was 50% or less of the growth rate in the untreated group.
• Test Example 4 Control test against corn smut (Ustilago maydis) Compounds of the present invention 1-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2- 10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-17, 3-1, 3-4, 8-1, 1-1, 1-8, 2-25, 2-26, 2-27, 2-33, 2-34, 2-35, 2-36, 2-37, 2-39, 2-41, 2-42, 8-8, 8-9, 8- Dilute with DMSO to contain 150 ppm of 11, 8-12, 8-13, 8-14, 8-16, 8-17, 8-18, 10-5, or 2-32 and titer plates (96 wells).
• Test Example 5 Control test against barley cloud fungus (Rhynchosporium secalis) Compound 1-2, 1-3, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2- 8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 3-1, 3-4, 3-6, 3-7, 6-2, 6-3, 6-4, 6-5, 7-1, 8-1, 8-2, 8-3, 8-4, 9-1, 1-1, 1- 8, 1-9, 1-10, 1-11, 1-12, 1-13, 2-25, 2-26, 2-27, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 8-8, 8-9, 8-10, 8-11, 8-12, 8- Contains 150 ppm of 13, 8-14, 8-15, 8-16, 8-17, 8-18, 8-19, 8-20, 8-21, 9-6, 10-5, or 11-3 After diluting with DMSO and dispensing 1 ⁇ L into a
• the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of barley cloud fungus.
• the growth rate in each group treated with the compound of the present invention was 50% or less of the growth rate in the untreated group.
• Test Example 6 Control test against Botrytis cinerea cucumber Compound 1-2, 1-3, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2 of the present invention -8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 3-1, 3-4, 3-6 , 3-7, 6-2, 6-3, 6-4, 6-5, 7-1, 8-1, 8-2, 8-3, 8-4, 9-1, 1-1, 1 -8, 1-9, 1-10, 1-12, 1-13, 2-25, 2-26, 2-27, 2-32, 2-33, 2-34, 2-35, 2-36 , 2-37, 2-39, 2-40, 2-41, 2-42, 8-8, 8-9, 8-10, 8-11, 8-12, 8-13, 8-14, 8 Dilute with DMSO to contain 150 ppm of -15, 8-16, 8-17, 8-18, 8-19, 8-20, 8-21, 9-6, 10-5, or 11-3.
• Test Example 7 Control test against Cladosporium carpophilum Compounds of the present invention 1-2, 1-3, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2- 8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 3-1, 3-4, 3-6, 3-7, 6-2, 6-3, 6-5, 7-1, 8-1, 8-2, 8-3, 8-4, 9-1, 1-1, 1-8, 1- 10, 1-11, 1-12, 1-13, 2-25, 2-26, 2-27, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-39, 2-40, 2-41, 2-42, 8-8, 8-9, 8-10, 8-11, 8-12, 8-13, 8-14, 8-15, 8- Dilute with DMSO to contain 150 ppm of 16, 8-17, 8-18, 8-19, 8-20, 8-21, 9-6, or 10-5, 1 ⁇ L in titer plate (96 wells).
• Test Example 8 Control test against rice sesame leaf blight (Cochliobolus miyabeanus) Compounds 1-2, 1-3, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 3-1, 3-4, 3- 6, 3-7, 6-1, 6-2, 6-3, 6-4, 6-5, 7-1, 8-1, 8-2, 8-3, 8-4, 9-1, 1-1, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 2-25, 2-26, 2-27, 2-32, 2-33, 2- 34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 8-8, 8-9, 8-10, 8-11, 8-12, 8-13, 8-14, 8-15, 8-16, 8-17, 8-18, 8-19, 8-20, 8-21, 9-6, 10-5, or 11 After diluting with DMSO so as to contain -3 at 150
• This plate was cultured at 23 ° C. for 3 days to grow rice sesame leaf blight, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of rice sesame leaf blight.
• the growth rate in each group treated with the compound of the present invention was 50% or less of the growth rate in the untreated group.
• Test Example 9 Control test for soybean rust (Phakopsora pachyrhizi) The true leaves of soybean (variety: Kurosengoku) were cut out to a diameter of 1 cm to prepare leaf discs. After 1 mL of agar medium (agar concentration 1.2%) was dispensed into each well of the 24-well microplate, one leaf disk was placed on the agar medium of each well. To a mixture of 0.5 ⁇ L of Solpol® 1200 KX, 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 a predetermined concentration of the test compound.
• the resulting mixture was sprayed at 10 ⁇ L per leaf disc.
• the soybean rust fungi with an amino acid substitution F129L the mitochondrial cytochrome b protein (Phakopsora pachyrhizi) aqueous suspension (1.0 ⁇ 10 5 / mL) of spores was inoculated by spraying on leaf disks. After inoculation, it was placed in an artificial meteorological device (lighted for 6 hours, turned off for 18 hours, temperature 23 ° C., humidity 60%).
• the leaf disc was air-dried until there were no water droplets on the surface, and the leaf disc was placed in the artificial meteorological instrument again for 12 days. After that, the lesion area of soybean rust was investigated.
• the predetermined concentration was set to 50 ppm, and the compound of the present invention 1-2, 1-3, 2-1, 2-3, 2-4, 2-5, 2-6, 2-7, 2- 8, 2-10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 2-18, 3-1, 3-4, 3-6, 3-7, 3-8, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 5-5, 5-8, 5-10, 5-11, 6- 1, 6-2, 6-3, 6-4, 6-5, 6-6, 6-7, 6-8, 7-1, 8-1, 8-2, 8-3, 8-4, 8-6, 8-7, 9-1, 9-2, 9-3, 9-4, 9-5, 10-1, 10-2, 10-3, 1-1, 1-8, 1- 10, 1-11, 1-13,
• Test Example 10 Control test for rice blast (Pyricularia oryzae) A plastic pot was filled with soil, and rice (variety; Hinohikari) was sown in the plastic pot and cultivated in a greenhouse for 20 days. Then, the compound 2-9 or 2-15 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so as to have a concentration of 200 ppm, and the obtained mixture is used as the above-mentioned rice leaf. The foliage was sprayed so that it adhered sufficiently to the surface.
• the rice After spraying, the rice is air-dried and left at 24 ° C in the daytime and 20 ° C at night under high humidity for 6 to 7 days while contacting the sprayed rice with the rice seedling (variety; Hinohikari) infected with the rice blast fungus. After that, the lesion area was investigated. As a result, the lesion area in the rice treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated rice.
• Test Example 11 Control test for barley net spot disease (Pyrenophora teres) A plastic pot was filled with soil, and barley (variety; Nishinohoshi) was sown in the plastic pot and cultivated in a greenhouse for 7 days. Compounds 1-3, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2 of the present invention formulated according to the method described in Formulation Example 6.
• the barley was placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 3 days, and then cultivated in the greenhouse for 7 days, and then the lesion area was investigated.
• the lesion area in the barley treated with each compound of the present invention was 30% or less of the lesion area in the untreated barley.
• Test Example 12 Control test for wheat rust (Puccinia recondita) A plastic pot was filled with soil, and wheat (variety; white gane) was sown in the plastic pot and cultivated in a greenhouse for 9 days. Compounds of the present invention formulated according to the method described in Preparation Example 6 1-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-10, 2 -11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 3-1, 3-4, 3-6, 3-7, 6-1, 6-2 , 6-3, 7-1, 8-1, 8-2, 8-3, 8-6, 9-1, 1-1, 2-27, 2-36, 2-37, 8-8, 8 Concentrations of -9, 8-11, 8-12, 8-13, 8-14, 8-15, 8-16, 8-17, 8-18, 8-21, 9-6, or 10-5 The mixture was mixed with water so as to have a concentration of 200 ppm, and the obtained mixture was sprayed on the foliage so as to sufficiently adhere to the
• the wheat was air-dried, cultivated at 20 ° C. under lighting for 5 to 7 days, and then sprinkled with spores of wheat rust fungus and inoculated. After inoculation, wheat was placed at 23 ° C. in dark and humid for 1 day, and then cultivated at 20 ° C. under lighting for 8 days, and the lesion area was investigated. As a result, the lesion area in the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated wheat.
• Test Example 13 Control test for wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, and wheat (variety; apogee) was sown in the plastic pot and cultivated in a greenhouse for 10 days. Compounds of the present invention formulated according to the method described in Preparation Example 6 1-2, 1-3, 2-2, 2-3, 2-4, 2-5, 2-7, 2-8, 2 -9, 2-10, 2-11, 2-12, 2-14, 2-15, 2-16, 2-17, 3-1, 3-4, 3-6, 3-7, 6-1 , 6-3, 6-5, 7-1, 8-1, 8-2, 8-3, 8-4, 8-6, 8-7, 9-1, 1-11, 1-13, 2 -25, 2-26, 2-27, 2-32, 2-33, 2-34, 8-8, 8-9, 8-11, 8-12, 8-13, 8-14, 8-15 , 8-16, 8-17, 8-18, 8-19, 8-21, 9-6, 10-5, 10-6, 11-1, or 11-2 with water so that the concentration is 200
• the obtained mixture was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the wheat.
• the wheat was air-dried, and 4 days later, a water suspension containing spores of Zymoseptoria trifolia was spray-inoculated.
• the wheat was placed under high humidity at 18 ° C. for 3 days, then cultivated under illumination for 14 to 18 days, and then the lesion area was investigated.
• the lesion area in the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated wheat.
• Test Example 14 Control test for wheat leaf blight (Septoria tritici) Fill a plastic pot with soil, sow wheat (variety; apogee) in it, cultivate it in a greenhouse for 10 days, and suspend wheat leaf blight spores in water. The liquid was sprayed. After inoculation, the wheat was placed under high humidity at 18 ° C.
• the mixture was mixed, and the obtained mixture was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the wheat. After spraying, the wheat was air-dried and left under illumination for 14 to 18 days, and then the lesion area was investigated. As a result, the lesion area in the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated wheat.
• Test Example 15 Control test against tomato epidemic (Phytophthora infestans) Soil was filled in a plastic pot, tomatoes (varieties; patio) were sown in the plastic pots, and the plants were cultivated in a greenhouse for 20 days.
• -16, 3-1, 3-4, 6-2, 8-9, 9-1, or 11-3 are mixed with water to a concentration of 200 ppm, and the resulting mixture is the above tomato leaf.
• the foliage was sprayed so that it adhered sufficiently to the surface.
• the tomatoes After spraying, the tomatoes were air-dried, and one day later, a water suspension containing spores of Phytophthora tomatoes was spray-inoculated. After inoculation, the tomatoes were placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 1 day, then cultivated in the greenhouse for 4 days, and then the lesion area was investigated. As a result, the lesion area in the tomatoes treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated tomatoes.
• Test Example 16 Control test for soybean rust (Phakopsora pachyrhizi) Soil was filled in a plastic pot, soybean (variety; Kurosengoku) was sown in it, and it was grown in a greenhouse for 10 to 14 days.
• Compounds of the present invention formulated according to the method described in Formulation Example 6 1-2, 1-3, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2 -10, 2-11, 2-12, 2-13, 2-14, 2-15, 2-16, 2-17, 3-1, 3-4, 3-6, 3-7, 6-1 , 6-2, 6-3, 6-4, 8-1, 8-2, 8-3, 8-4, 8-6, 8-7, 9-1, 1-1, 1-13, 2 -25, 2-26, 2-27, 2-32, 2-33, 2-34, 2-35, 2-39, 2-40, 8-8, 8-9, 8-10, 8-11 , 8-12, 8-13, 8-14, 8-15, 8-16, 8-17, 8-18, 8-19, 8-20, 8-21, 9-6, or
• the soybeans After spraying, the soybeans were air-dried, and 2 to 5 days later, a water suspension of soybean rust spores was spray-inoculated. After inoculation, the soybeans were placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 1 to 2 days, and then cultivated in the greenhouse for 12 days, and then the lesion area was investigated. As a result, the lesion area in the soybeans treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated soybeans.
• Test Example 17 Control test for soybean rust (Phakopsora pachyrhizi) Fill a plastic pot with soil, sow soybean (variety; Kurosengoku) in it, grow it in a greenhouse for 10 days, and water it with spores of soybean rust fungus. The turbid liquid was spray-injected. After inoculation, the soybean is placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 1 day, then cultivated in the greenhouse for 2 days, and then the compound 1 of the present invention formulated according to the method described in Formulation Example 6.
• the soybeans were air-dried and cultivated in a greenhouse for 8 days, and then the lesion area was investigated. As a result, the lesion area in the soybeans treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated soybeans.
• Test Example 18 Control test for soybean spot disease (Cercospora sojina) A plastic pot was filled with soil, soybean (variety; Tachinagaha) was sown in the plastic pot, and the plant was grown in a greenhouse for 13 days.
• soybeans were air-dried, and one day later, a water suspension of soybean spot disease spores was spray-inoculated. After inoculation, soybeans were placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 3 days, then cultivated in the greenhouse for 16 days, and then the lesion area was investigated. As a result, the lesion area in the soybeans treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated soybeans.
• Test Example 19 Control test for tomato ring pattern disease (Alternaria solani) A plastic pot was filled with soil, and tomatoes (varieties; patio) were sown in the plastic pots and grown in a greenhouse for 20 days.
• the tomatoes After spraying, the tomatoes were air-dried, and one day later, a water suspension of tomato ring-spotted spores was spray-inoculated. After inoculation, the tomatoes were placed at 18 ° C. and under high humidity for 6 days, and then the lesion area was investigated. As a result, the lesion area in the tomatoes treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated tomatoes.
• Test Example 20 Control test for Sclerotinia sclerotiorum A plastic pot was filled with soil, and green beans (varieties; long bean beans) were sown and grown in a greenhouse for 8 days. Compounds of the present invention formulated according to the method described in Formulation Example 6 1-2, 1-3, 2-3, 2-4, 2-5, 2-7, 2-8, 2-9, 2 -10, 2-11, 2-13, 2-15, 3-1, 3-4, 6-3, 8-1, 8-2, 8-3, 8-6, 8-7, 2-27 , 8-8, 8-9, 8-10, 8-12, 8-13, 8-14, 8-18, 8-21, 9-6, or 10-5 so that the concentration is 200 ppm.
• the mixture was mixed with water, and the obtained mixture was sprayed on the stems and leaves so as to sufficiently adhere to the leaf surface of the green beans.
• the common bean was air-dried, and a PDA medium containing hyphae of Sclerotinia scleroides was placed on the leaf surface of the common bean.
• all green beans were kept under high humidity only at night, and the lesion area was investigated 4 days after inoculation.
• the lesion area in the kidney beans treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated kidney beans.
• Test method 21 Test on cotton aphid
• the test compound is prepared according to the method described in Preparation Example 6, water containing 0.03% by volume of the spreading agent is added thereto, and a diluted solution containing the test compound at a predetermined concentration.
• a diluted solution containing the test compound at a predetermined concentration.
• Control value (%) ⁇ 1- (Cb x Tai) / (Cai x Tb) ⁇ x 100
• Cb Number of test insects in the untreated plot
• Cai Number of surviving insects at the time of survey in the untreated plot
• Tb Number of test insects in the treated plot
• Tai Number of surviving insects at the time of survey in the treated plot
• Test Example 21 As a result of conducting a test according to the test method 21 using the following compound of the present invention as a test compound at a predetermined concentration of 500 ppm, all of the following compounds of the present invention showed a control value of 90% or more.
• Compounds of the present invention 1-2, 8-3, 8-4, 9-1, 2-41
• Test method 22 Test on brown planthopper
• the test compound is prepared according to the method described in Preparation Example 6, water containing 0.03% by volume of the spreading agent is added thereto, and a diluted solution containing the test compound at a predetermined concentration is added.
• Test Example 22 As a result of conducting a test according to Test Method 22 using the following compound of the present invention as a test compound at a predetermined concentration of 500 ppm, all of the following compounds of the present invention showed an insecticidal rate of 90% or more.
• Compounds of the present invention 1-2, 8-8
• Test Example 23 As a result of conducting a test according to Test Method 23 using the following compound of the present invention as a test compound at a predetermined concentration of 500 ppm, all of the following compounds of the present invention showed an insecticidal rate of 80% or more.
• Compounds of the present invention 1-2, 8-4
• Test Example 24 As a result of conducting a test according to the test method 24 using the following compound of the present invention as a test compound at a predetermined concentration of 500 ppm, all of the following compounds of the present invention showed an insecticidal rate of 80% or more.
• Compounds of the present invention 1-2, 2-6, 8-3, 8-4, 1-1, 2-32, 8-8, 8-9
• Test method 25 Test against Nami spider mite
• the test compound is prepared according to the method described in Preparation Example 6, water containing 0.03% by volume of the spreading agent is added thereto, and a diluted solution containing the test compound at a predetermined concentration is prepared.
• Control value (%) ⁇ 1- (Cb x Tai) / (Cai x Tb) ⁇ x 100
• Cb Number of test insects in the untreated plot
• Cai Number of surviving insects at the time of survey in the untreated plot
• Tb Number of test insects in the treated plot
• Tai Number of surviving insects at the time of survey in the treated plot
• Test Example 25 As a result of conducting a test according to Test Method 25 using the following compound of the present invention as a test compound at a predetermined concentration of 500 ppm, all of the following compounds of the present invention showed a control value of 90% or more.
• Compounds of the present invention 1-2, 2-6, 8-2, 8-4, 9-1, 1-1, 1-8, 1-11, 1-12, 2-32, 2-33, 2- 34, 2-41, 8-21
• the compound of the present invention has a control effect on pests and can be used for pest control.

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