Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/62—Halogen-containing esters
  • C07C69/63—Halogen-containing esters of saturated acids
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/34—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
  • 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
  • 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
• • 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
  • A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
• • 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
  • 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
• • 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
  • 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
• • 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
  • 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
• • 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
  • 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
  • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
  • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P3/00—Fungicides
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/02—Acaricides
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/04—Insecticides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/16—Amides, e.g. hydroxamic acids
  • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
  • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
  • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
  • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
  • A61K31/415—1,2-Diazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
  • A61K31/425—Thiazoles
  • A61K31/426—1,3-Thiazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
  • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
  • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
  • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
  • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
  • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
  • C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
  • C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
  • C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C255/00—Carboxylic acid nitriles
  • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
  • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
  • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
  • C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • 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
  • C07C69/736—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • 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
  • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • 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
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/61—Halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
  • C07D277/30—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
• • 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
  • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D333/28—Halogen atoms
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23K—FODDER
  • A23K20/00—Accessory food factors for animal feeding-stuffs
  • A23K20/10—Organic substances
  • A23K20/111—Aromatic compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

• Patent Document 1 describes a phenylacetic acid derivative.
• the purpose of the present invention is to provide a compound that has excellent control efficacy against pests.
• R 8 and R 9 are the same or different, a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group G, substituted with one or more substituents selected from group E C3-C6 cycloalkyl group optionally substituted, phenyl group, 5-6 membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6 membered aromatic heterocyclic group are substituted with one or more groups selected from group F group], or represents a hydrogen atom
• R 10 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group G, C3-C6 optionally substituted with one or more substituents selected from group E A cycloalkyl group, a phenyl group, or a 5- to 6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group F good ⁇
• R 11 represents a C
• Group D C1-C6 alkoxy group, C1-C6 alkylthio group ⁇ the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from group G ⁇ , C3 -C6 cycloalkyl group, 3-8 membered non-aromatic heterocyclic group ⁇ the C3-C6 cycloalkyl group and the 3-8 membered non-aromatic heterocyclic group are substituted with one or more substituents selected from group E ⁇ , a C6-C10 aryl group,
• Group F C1-C3 chain hydrocarbon group, C3-C6 cycloalkyl group, C1-C3 alkoxy group, C1-C3 alkylthio group ⁇ said C1-C3 chain hydrocarbon group, said C3-C6 cycloalkyl group, said The C1-C3 alkoxy group and said C1-C3 alkylthio group may be substituted with one or more substituents selected from group G ⁇ , a group consisting of a halogen atom, a cyano group, a nitro group and a hydroxy group.
• Group G a group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group and a halogen atom.
• the compound represented by hereinafter referred to as the compound N of the present invention), or its N oxide or a salt thereof (hereinafter, the compound represented by formula (I), or its N oxide or a salt thereof is referred to as the compound of the present invention ).
• n is 1; R 1 and R 2 are the same or different and are a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom; R 2 is attached to the 4- or 5-position, E is a phenyl group, a 5- to 6-membered aromatic heterocyclic group ⁇ the phenyl group and the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group H ⁇ , R 3 —O—N ⁇ C(R 4 )—, R 5 —C ⁇ C—, R 6 O—, or a C5-C6 cycloalkenyl group, R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group G, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or R 7 CH 2 —, R 4 is a C1-
• Group H C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, C1-C3 alkoxy group, trifluoromethoxy group, C3-C4 cycloalkyl group, halogen atom, cyano group, and nitro A group consisting of groups.
• Group I consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a phenyl group ⁇ the C1-C3 alkoxy group and the phenyl group may be substituted with one or more halogen atoms ⁇ , and a halogen atom group.
• Group J a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group ⁇ the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted with one or more halogen atoms ⁇ , the group consisting of C3-C6 cycloalkyl groups, halogen atoms, cyano groups and nitro groups;
• E is a phenyl group, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group ⁇ the phenyl group, the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group are one or more selected from Group H ], R 5 —C ⁇ C—, R 6 O—, or a C5-C6 cycloalkenyl group, the compound according to [2] or its N oxide, or a salt thereof .
• a seed or vegetative reproductive organ containing an effective amount of the compound according to any one of [1] to [3] or its N oxide or salt thereof, or an effective amount of the composition according to [5] .
• Formula (II): [In the formula, The combination of X and L is a combination in which X is a nitrogen atom and L is an oxygen atom or NH; or represents a combination in which X is CH and L is an oxygen atom; E a is R 12a C(O)—, R 12a C( N—OH)—, hydroxy group, B(OH) 2 , 4,4,5,5-tetramethyl-1,3,2-dioxaborolane -2-yl group, or represents a halogen atom, R 1a and R 2a are the same or different and represent a methyl group or a halogen atom; R 12a represents a C1-C3 alkyl group or a hydrogen atom.
• a halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
• a substituent is substituted with two or more halogen atoms, each of those halogen atoms may be the same or different.
• substituent is substituted with two or more groups or atoms selected from a specific group (for example, the group consisting of C1-C3 alkyl groups and halogen atoms), each of these groups or atoms may be the same or different.
• substituents selected from group X may be any of A, B, C, D, E, F, G, H, I, J, and K or one
• substituents may be the same or different.
• CX-CY used herein means that the number of carbon atoms is from X to Y.
• C1-C6 means 1 to 6 carbon atoms.
• a chain hydrocarbon group represents an alkyl group, an alkenyl group or an alkynyl group.
• alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, A hexyl group and a decyl group are included.
• alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3- butenyl, 4-pentenyl, 5-hexenyl, and 9-decenyl groups.
• alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, 5 -hexynyl group and 9-decynyl group.
• Alkoxy groups include, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy groups.
• alkylthio groups include methylthio, ethylthio, propylthio, isopropylthio, butylthio, tert-butylthio, pentylthio, and hexylthio groups.
• Cycloalkyl groups include, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups.
• Cycloalkenyl groups include, for example, cyclopentenyl and cyclohexenyl groups.
• Aryl groups include, for example, phenyl, indenyl, indanyl, naphthyl, and tetrahydronaphthyl groups.
• aromatic heterocyclic groups include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, and pyridyl groups.
• pyridazinyl pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, indazolyl, benzimidazolyl, imidazopyridyl, benzothiophenyl, benzofuranyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalinyl. be done.
• a soybean rust fungus having an F129L amino acid substitution in the mitochondrial cytochrome b protein has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein, and as a result of the mutation, the F129L amino acid substitution occurs, resulting in QoI It is a fungicide-resistant soybean rust fungus (scientific name: Phakopsora pachyrhizi).
• Stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
• the present invention includes each stereoisomer and mixtures of stereoisomers in any proportion.
• Geometric isomers include, for example, the following structures.
• Compound N of the present invention or its N oxide can be mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid and benzoic acid to obtain hydrochloride, sulfate, nitrate, phosphate, acetate and benzoate. may form an acid addition salt such as
• Embodiments of the compound N of the present invention include the following compounds.
• a compound N in which E is R 3 —ON C(R 4 )— in the compound N of the present invention.
• R 3 is a C1-C6 chain hydrocarbon group ⁇ the C1-C6 chain hydrocarbon group is one or more selected from the group consisting of a C3-C4 cycloalkyl group and a halogen atom; optionally substituted with a substituent ⁇ , or R 7 CH 2 —, R 4 is a methyl group or a hydrogen atom, R 7 is a phenyl group or a 5- to 6-membered aromatic heterocyclic group ⁇ the The phenyl group and the 5- to 6-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group K ⁇ .
• Group K a group consisting of a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms and a halogen atom.
• R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
• E is a phenyl group optionally substituted with one or more substituents selected from group A;
• E is a 5- to 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group B;
• Aspect 10 In the compound N of the present invention, E is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H.
• E is a pyridyl group, a thienyl group, a thiazolyl group, or a pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group are selected from Group H 1 optionally substituted with any of the above substituents ⁇ .
• E is a pyridyl group, a thienyl group, a thiazolyl group, or a pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group are selected from group K 1 optionally substituted with any of the above substituents ⁇ .
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , a C5-C6 cycloalkenyl group, R 3 —O —N ⁇ C(R 4 )—, R 5 —C ⁇ C—, or R 6 O—, and R 3 is a C1-C6 chain hydrocarbon group ⁇ the C1-C6 chain hydrocarbon group is optionally substituted with one or more substituents selected from the group consisting of a C3-C4 cycloalkyl group and a halogen atom ⁇ , or R 7 CH 2 —, R
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , a 5- or 6-membered aromatic heterocyclic group ⁇
• the 5- to 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H ⁇ , C3- optionally substituted with one or more substituents selected from group C C7 cycloalkenyl group, R 5 —C ⁇ C—, or R 6 O—
• R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group ⁇ the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms ⁇ .
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , a C5-C6 cycloalkenyl group, R 5 -C ⁇ C— or R 6 O—, R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 6 is substituted with one or more substituents selected from group I
• E is
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl a group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , R 5 —C ⁇ C—, or R 6 O—, R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 6 is C2- optionally substituted with one or more substituents selected from group I A compound that is a C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , a 5- or 6-membered aromatic heterocyclic group ⁇
• the 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group H ⁇ , or R 5 -C ⁇ C-, where R 5 is a C1-C6 chain Formula hydrocarbon group or C3-C6 cycloalkyl group ⁇ the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may be substituted with one or more halogen atoms ⁇ .
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl a group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , or R -C ⁇ C- , A compound in which R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , a 5- or 6-membered aromatic heterocyclic group ⁇ The 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group H ⁇ , or a compound represented by R 6 O-.
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , pyridyl group, thienyl group, thiazolyl group, pyrazolyl a group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from Group K ⁇ , or R 6 O—, and R 6 is , a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from Group A ⁇ , R 5 —C ⁇ C—, or R 6 O— and R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group ⁇ the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group are one or more halogen atoms optionally substituted with ⁇ .
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , R 5 —C ⁇ C—, or R 6 O—, R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R 6 is C2 optionally substituted with one or more substituents selected from group I - A compound that is a C6 chain hydrocarbon group or a C3-C4 cycloalkyl group.
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , or a 5- or 6-membered aromatic heterocyclic group. ⁇ The 5- to 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group H ⁇ .
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , a pyridyl group, a thienyl group, a thiazolyl group, or A compound which is a pyrazolyl group ⁇ the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be substituted with one or more substituents selected from group K ⁇ .
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from Group A ⁇ , or R 5 -C ⁇ C- , R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group ⁇ the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group are substituted with one or more halogen atoms; may ⁇ .
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from Group H ⁇ , or R 5 -C ⁇ C- , R 5 is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group A ⁇ , or R 6 O—.
• E is a phenyl group ⁇ the phenyl group may be substituted with one or more substituents selected from group H ⁇ , or R 6 O—, and R 6 is a C2-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
• Aspect 33 The compound according to Aspect 2, wherein X is CH and L is an oxygen atom.
• Aspect 34 The compound according to Aspect 3, wherein X is CH and L is an oxygen atom.
• Aspect 35 The compound according to Aspect 4, wherein X is CH and L is an oxygen atom.
• Aspect 36 The compound according to Aspect 5, wherein X is CH and L is an oxygen atom.
• Aspect 37 The compound according to Aspect 6, wherein X is CH and L is an oxygen atom.
• Aspect 38 The compound according to Aspect 7, wherein X is CH and L is an oxygen atom.
• Aspect 39 The compound according to Aspect 8, wherein X is CH and L is an oxygen atom.
• Aspect 40 The compound according to Aspect 9, wherein X is CH and L is an oxygen atom.
• R 1 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom. .
• R 1 is a methyl group, a methoxy group, or a halogen atom.
• R 2 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom. .
• R 2 is a methyl group, a methoxy group, or a halogen atom.
• R 1 and R 2 are the same or different and are a C1-C3 alkyl group optionally substituted with one or more halogen atoms, methoxy A compound that is a group or a halogen atom.
• R 1 is a methyl group, a methoxy group, or a halogen atom, and R 2 is substituted with one or more halogen atoms.
• R 1 is a methyl group
• R 2 is a C1-C3 alkyl group optionally substituted with one or more halogen atoms, methoxy A compound that is a group or a halogen atom.
• R 1 and R 2 are methyl groups.
• n is 1.
• Aspect 90 The compound according to Aspect 69, wherein n is 1 and R 2 is bonded to the 4-position.
• Aspect 94 The compound according to Aspect 73, wherein n is 1 and R 2 is bonded to the 4-position.
• n 1 and R 2 is bonded to the 4-position is represented by the formula (I-4) [In the formula, symbols have the same meanings as defined in [1]. ] is a compound represented by Compounds of embodiments 88-94 can also be represented by formula (I-4).
• the compound represented by formula (A1) (hereinafter referred to as compound (A1)) is a compound represented by formula (B1) (hereinafter referred to as compound (B1)) and the compound represented by formula (M1) (hereinafter referred to as compound (M1)) in the presence of a palladium catalyst and a base.
• E 1 is a C6-C10 aryl group or a 5- to 10-membered aromatic heterocyclic group ⁇ the C6-C10 aryl group and the 5- to 10-membered aromatic heterocyclic group are 1 selected from Group A optionally substituted with the above substituents ⁇ , and M 1 represents B(OH) 2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group , X 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a triflyloxy group, etc., and other symbols have the same meanings as above.
• the reaction is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), Ethers such as dimethoxyethane (hereinafter referred to as ethers); Halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); Dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone ( amides such as NMP) (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles) ); water and
• Palladium catalysts used in the reaction include tris(dibenzylideneacetone)dipalladium(0) (hereinafter referred to as Pd 2 (dba) 3 ), tetrakis(triphenylphosphine)palladium(0) (hereinafter referred to as Pd(PPh 3 ) 4 ), and ⁇ 1,1′-bis(diphenylphosphino)ferrocene ⁇ palladium(II) dichloride (hereinafter referred to as PdCl 2 (dppf)).
• Pd 2 (dba) 3 tris(dibenzylideneacetone)dipalladium(0)
• Pd(PPh 3 ) 4 tetrakis(triphenylphosphine)palladium(0)
• PdCl 2 (dppf) ⁇ 1,1′-bis(diphenylphosphino)ferrocene ⁇ palladium(II) dichloride
• bases used in the reaction include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal hydrogen carbonates such as sodium and potassium hydrogen carbonate (hereinafter referred to as alkali metal hydrogen carbonates); sodium fluoride and tripotassium phosphate.
• organic bases such as triethylamine and pyridine
• alkali metal carbonates such as sodium carbonate and potassium carbonate
• alkali metal hydrogen carbonates such as sodium and potassium hydrogen carbonate
• sodium fluoride and tripotassium phosphate sodium fluoride and tripotassium phosphate.
• a ligand may be used in the reaction, if necessary.
• Ligands used in the reaction include triphenylphosphine, xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2- dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane and the like.
• the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B1).
• the compound (M1) is usually used at a ratio of 1 to 10 mol
• the palladium catalyst is usually used at a ratio of 0.01 to 1 mol
• the base is usually used at a ratio of 1 to 10 mol, relative to 1 mol of the compound (B1).
• the reaction temperature is usually within the range of 0-150°C.
• the reaction time is usually within the range of 0.1 to 120 hours.
• compound (A1) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M1) is known or can be produced according to known methods.
• Manufacturing method B Compound (A1) is prepared by reacting a compound represented by formula (B2) (hereinafter referred to as compound (B2)) and a compound represented by formula (M2) (hereinafter referred to as compound (M2)) with a palladium catalyst and a base. It can be produced by reacting in the presence. [In the formula, symbols have the same meanings as described above. ] The reaction can be carried out according to production method A using compound (M2) in place of compound (B1) and compound (B2) in place of compound (M1). Compound (M2) is known or can be produced according to known methods.
• the compound represented by the formula (A2) (hereinafter referred to as compound (A2)) is obtained by combining the compound (B1) and the compound represented by the formula (M3) (hereinafter referred to as compound (M3)) with a metal catalyst and a base. It can be produced by reacting in the presence.
• a metal catalyst and a base a metal catalyst and a base.
• the reaction is usually carried out in a solvent. Solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures of two or more thereof.
• Metal catalysts used in the reaction include, for example, bis(triphenylphosphine)palladium(II) dichloride and copper(I) iodide.
• bases used in the reaction include organic bases.
• the compound (M3) is usually used at a ratio of 1 to 10 mol
• the metal catalyst is usually used at a ratio of 0.01 to 1 mol
• the base is usually used at a ratio of 1 to 10 mol, relative to 1 mol of the compound (B1). Used.
• the reaction temperature is usually within the range of 0-150°C.
• the reaction time is usually within the range of 0.1 to 120 hours.
• compound (A2) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M3) is known or can be produced according to known methods.
• the compound represented by formula (A3) (hereinafter referred to as compound (A3)) is a compound represented by formula (B3) (hereinafter referred to as compound (B3)) and the compound represented by formula (M4) (hereinafter referred to as It can be produced by reacting a compound (M4)) or a salt thereof.
• Salts of compound (M4) include, for example, hydrochloride and sulfate.
• the reaction is usually carried out in a solvent. Solvents used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; Mixtures of the above are included.
• a base may be added to the reaction, if necessary.
• Bases used in the reaction include, for example, organic bases; alkali metal carbonates; alkali metal hydrogencarbonates; sodium hydride and tripotassium phosphate.
• the base is generally used in a proportion of 1 to 10 mol per 1 mol of compound (B3).
• compound (M4) is generally used in a proportion of 1 to 10 mol per 1 mol of compound (B3).
• the reaction temperature is usually within the range of 0-150°C.
• the reaction time is usually within the range of 0.1 to 120 hours.
• the compound (A3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (A3) can also be produced according to the method described in International Publication No. 98/043949 and the like.
• Compound (M4) is known or can be produced according to known methods.
• Compound (A3) is prepared by reacting a compound represented by formula (B4) (hereinafter referred to as compound (B4)) and a compound represented by formula (M5) (hereinafter referred to as compound (M5)) in the presence of a base. It can be produced by reacting.
• a compound represented by formula (B4) hereinafter referred to as compound (B4)
• a compound represented by formula (M5) hereinafter referred to as compound (M5)
• the reaction is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
• Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogencarbonates, sodium hydride and tripotassium phosphate.
• the compound (M5) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B4).
• the reaction temperature is usually within the range of -20 to 150°C.
• the reaction time is usually within the range of 0.1 to 48 hours.
• the compound (A3) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M5) is known or can be produced according to known methods.
• Manufacturing method F The compound represented by formula (A4) (hereinafter referred to as compound (A4)) is obtained by reacting compound (B1) and the compound represented by formula (M6) (hereinafter referred to as compound (M6)) with a metal catalyst and a base. It can be produced by reacting in the presence.
• Z 1 represents a nitrogen atom or CR 51
• Z 2 represents a nitrogen atom or CR 52
• Z 3 represents a nitrogen atom or CR 53
• Z 4 represents a nitrogen atom or CR 54 (with the proviso that Z 1 , Z 2 , Z 3 and Z 4 are all nitrogen atoms)
• R 51 , R 52 , R 53 and R 54 are the same or different and one or more substituents selected from group E
• a C3-C6 cycloalkyl group optionally substituted with a group, a C1-C6 chain hydrocarbon group, a C1-C3 alkylthio group ⁇ the C1-C6 chain hydrocarbon group and the C1-C3 alkylthio group are group G optionally substituted with one or more substituents selected from]
• a phenyl group, a 5-6 membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6 membered aromatic heterocyclic group are selected from Group F , OR 13
• the reaction is usually carried out in a solvent.
• Solvents used in the reaction include, for example, ethers, hydrocarbons, amides, water and mixtures of two or more thereof.
• Metal catalysts used in the reaction include copper (I) iodide, copper (I) bromide, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile) copper catalysts such as copper (I) hexafluorophosphate and copper (I) 2-thiophenecarboxylate; and nickel catalysts such as bis(cyclooctadiene) nickel (0) and nickel (II) chloride.
• bases include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium fluoride and tripotassium phosphate.
• a ligand and/or an alkali metal halide may be used for the reaction, if desired.
• ligands include triphenylphosphine, xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphos Phino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2 -aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine,
• the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B1).
• Alkali metal halides include potassium fluoride, sodium fluoride, lithium chloride, sodium chloride and the like.
• the alkali metal halide is usually used in a proportion of 0.1 to 5 mol per 1 mol of compound (B1).
• the compound (M6) is usually used at a ratio of 1 to 10 mol
• the metal catalyst is usually used at a ratio of 0.01 to 2 mol
• the base is usually used at a ratio of 1 to 10 mol, relative to 1 mol of the compound (B1). Used.
• reaction temperature is usually in the range of -20°C to 200°C.
• reaction time is usually in the range of 0.1 to 48 hours.
• compound (A4) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M6) is known or can be produced according to known methods.
• the compound represented by formula (A5) (hereinafter referred to as compound (A5)) is a compound represented by formula (B5) (hereinafter referred to as compound (B5)) and the compound represented by formula (M7) (hereinafter referred to as compound (M7)) in the presence of phosphines and azodiesters.
• the symbols have the same meanings as described above.
• the reaction is usually carried out in a solvent. Solvents used in the reaction include, for example, hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; Phosphines include, for example, triphenylphosphine and trimethylphosphine.
• Azodiesters include, for example, diethyl azodicarboxylate, diisopropyl azodicarboxylate and bis(2-methoxyethyl) azodicarboxylate.
• the compound (M7) is usually used at a ratio of 1 to 10 mol
• the phosphine is usually used at a ratio of 1 to 10 mol
• the azodiester is usually used at a ratio of 1 to 10 mol with respect to 1 mol of the compound (B5).
• the reaction temperature is usually within the range of 0-150°C.
• the reaction time is usually within the range of 0.1 to 48 hours.
• compound (A5) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M7) is known or can be produced according to known methods.
• Manufacturing method H Compound (A5) can also be produced by reacting compound (B5) with a compound represented by formula (M8) (hereinafter referred to as compound (M8)) in the presence of a base.
• a compound represented by formula (M8) hereinafter referred to as compound (M8)
• the reaction is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
• Bases include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and tripotassium phosphate.
• the compound (M8) is generally used in an amount of 1 to 10 mol, and the base is generally used in an amount of 1 to 10 mol, per 1 mol of the compound (B5).
• the reaction temperature is usually within the range of -20 to 150°C.
• the reaction time is usually within the range of 0.1 to 48 hours.
• compound (A5) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M8) is known or can be produced according to known methods.
• the compound represented by formula (A6) (hereinafter referred to as compound (A6)) is a compound represented by formula (B6) (hereinafter referred to as compound (B6)) and the compound represented by formula (M9) (hereinafter referred to as A step of reacting a compound represented by formula (B7) (hereinafter referred to as compound (B7)) with a compound (M9) in the presence of a base (hereinafter referred to as step (I-1)) , and a step of reacting compound (B7) with a compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base (hereinafter referred to as step (I-2)).
• step (I-2) a step of reacting compound (B7) with a compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base (hereinafter referred to as step (I-2)).
• R 55 represents a C1-C4 alkyl group
• X 2 represents an iodine atom, a methoxysulfonyloxy group, a mesyloxy group, or a tosyloxy group, and other symbols have the same meanings as above.
• Step (I-1) is usually carried out in a solvent.
• Solvents used in the reaction include, for example, ethers, amides, and mixtures of two or more thereof.
• Bases used in the reaction include, for example, sodium hydride.
• the compound (M9) is generally used in an amount of 1 mol to 10 mol, and the base is generally used in an amount of 0.5 mol to 5 mol, per 1 mol of the compound (B6).
• the reaction time is usually within the range of 5 minutes to 72 hours.
• the reaction temperature is usually in the range of -20°C to 100°C.
• compound (B7) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M9) is a commercially available compound, or can be produced according to a known method.
• Step (I-2) is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
• Bases used in the reaction include, for example, organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, and sodium hydride.
• the compound (M10) is generally used in an amount of 1 to 10 mol
• the base is generally used in an amount of 1 to 20 mol, per 1 mol of the compound (B7).
• the reaction temperature is usually in the range of -20 to 100°C.
• the reaction time is usually within the range of 0.1 to 48 hours.
• compound (A6) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M10) is a commercially available compound, or can be produced according to a known method.
• the compound represented by formula (A7) (hereinafter referred to as compound (A7)) is a compound represented by formula (B26) (hereinafter referred to as compound (B26)) and the compound represented by formula (M12) (hereinafter referred to as a compound (M12)) in the presence of a base to obtain a compound represented by formula (B9) (hereinafter referred to as compound (B9)) (hereinafter referred to as step (K-1)) , and a step of reacting compound (B9) with compound (M10) in the presence of a base (hereinafter referred to as step (K-2)).
• R 56 represents a tert-butyl group or an isopentyl group, and other symbols have the same meanings as above. ]
• Step (K-1) is usually carried out in a solvent.
• Solvents used in the reaction include, for example, ethers, amides, alcohols, and mixtures of two or more thereof.
• Bases used in the reaction include, for example, sodium hydride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide (hereinafter referred to as alkali metal alkoxides).
• the compound (M12) is generally used in an amount of 1 mol to 10 mol
• the base is generally used in an amount of 1 mol to 5 mol, per 1 mol of the compound (B6).
• the reaction time is usually within the range of 5 minutes to 72 hours.
• reaction temperature is usually in the range of -20°C to 100°C.
• compound (B9) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M12) is a commercially available compound, or can be produced according to a known method.
• Step (K-2) can be carried out according to step (I-2) of production method I, using compound (B9) instead of compound (B7).
• the compound represented by formula (A8) (hereinafter referred to as compound (A8)) is a compound represented by formula (B10) (hereinafter referred to as compound (B10)) and the compound represented by formula (M13) (hereinafter referred to as compound (M13)) in the presence of a catalyst and a base.
• compound (B10) a compound represented by formula (B10)
• M13 the compound represented by formula (M13)
• the reaction can be carried out according to Production Method A using compound (M13) instead of compound (B1) and compound (B10) instead of compound (M1).
• Compound (M13) is a known compound, or can be produced according to a known method.
• N-oxide of the compound of formula (I) can be prepared by reacting the compound of formula (I) with an oxidizing agent.
• the reaction can be carried out, for example, according to the method described in US Patent Application Publication No. 2018/0009778 or International Publication No. 2016/121970.
• Reference manufacturing method 1 Compound (B7) is prepared by reacting compound (B6) with a compound represented by formula (M11) (hereinafter referred to as compound (M11)) to obtain a compound represented by formula (B8) (hereinafter referred to as compound (B8) and (hereinafter referred to as step (1-1)), and a step of reacting compound (B8) in the presence of an acid to obtain compound (B7) (hereinafter referred to as step (1-2)).
• M11 compound represented by formula (M11)
• step (1-1) a step of reacting compound (B8) in the presence of an acid to obtain compound (B7)
• step (1-2) can be manufactured by [In the formula, symbols have the same meanings as described above. ]
• Step (1-1) is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons, halogenated hydrocarbons, ethers, amides and mixtures of two or more thereof.
• compound (M11) is generally used in a proportion of 1 mol to 10 mol per 1 mol of compound (B6).
• the reaction time is usually within the range of 5 minutes to 72 hours.
• the reaction temperature is usually within the range of -20°C to 200°C.
• compound (B8) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M11) is a commercially available compound, or can be produced according to a known method.
• Step (1-2) is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more thereof.
• Acids used in the reaction include, for example, hydrochloric acid and acetic acid.
• the reaction temperature is usually within the range of -20 to 100°C.
• the reaction time is usually within the range of 0.1 to 48 hours.
• compound (B7) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• the compound represented by formula (B16) (hereinafter referred to as compound (B16)) is a compound represented by formula (B11) (hereinafter referred to as compound (B11)) and the compound represented by formula (M14) (hereinafter referred to as a compound (M14)) in the presence of a catalyst and a base to obtain a compound represented by formula (B12) (hereinafter referred to as compound (B12)) (hereinafter referred to as step (2-1) and a step of reacting compound (B12) in the presence of a base to obtain a compound represented by formula (B13) (hereinafter referred to as compound (B13)) (hereinafter referred to as step (2-2)); A step of reacting compound (B13) with compound (M11) to obtain a compound represented by formula (B14) (hereinafter referred to as compound (B14)) (hereinafter referred to as step (2-3)), compound ( B14) in the presence of an acid to obtain a
• Step (2-1) is usually carried out in a solvent.
• Solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water and mixtures of two or more thereof.
• catalysts used in the reaction include palladium catalysts such as palladium (II) acetate, Pd 2 (dba) 3 , Pd(PPh 3 ) 4 and PdCl 2 (dppf); Copper (I) chloride, copper (I) chloride, copper (I) oxide, copper (I) trifluoromethanesulfonate (I) benzene complex, tetrakis (acetonitrile) copper (I) hexafluorophosphate, copper (I) 2-thiophenecarboxylate ) and other copper catalysts.
• palladium catalysts such as palladium (II) acetate, Pd 2 (dba) 3 , Pd(PPh 3 ) 4 and P
• Bases used in the reaction include, for example, organic bases; alkali metal carbonates; alkali metal hydrogen carbonates; alkali metal phosphates such as tripotassium phosphate (hereinafter referred to as alkali metal phosphates); Acetates such as sodium (hereinafter referred to as acetates) can be mentioned.
• a ligand may be used in the reaction, if necessary.
• Ligands used in the reaction include triphenylphosphine, xantphos, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,1′-bis(diphenylphosphino)ferrocene, 2- Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl, tri-tert-butylphosphine, 1,2-bis(diphenylphosphino)ethane, pyridine-2-carboxylic acid, (L)-proline, trans-1,2-cyclohexane diamine, trans-N,N'-dimethylcyclohexane-1,2-di
• the ligand is usually used in a proportion of 0.01 to 1 mol per 1 mol of compound (B11).
• the compound (M14) is usually used at a ratio of 0.1 to 10 mol
• the catalyst is usually used at a ratio of 0.01 to 1 mol
• the base is usually used at a ratio of 1 to 10 mol, relative to 1 mol of the compound (B11).
• used in The reaction time is usually in the range of 5 minutes to 72 hours.
• the reaction temperature is usually in the range of -20°C to 200°C.
• the compound (B12) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Compound (M14) is a known compound, or can be produced according to a known method.
• Step (2-2) is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more thereof.
• Bases used in the reaction include, for example, alkali metal phosphates and alkali metal alkoxides. In the reaction, a base is generally used in a proportion of 1 to 20 mol per 1 mol of compound (B12).
• Step (2-3) can be carried out according to step (1-1) of Reference Production Method 1, using compound (B13) instead of compound (B6).
• Step (2-4) can be carried out according to step (1-2) of Reference Production Method 1, using compound (B14) instead of compound (B8).
• Step (2-5) can be carried out according to step (I-2) of production method I, using compound (B15) instead of compound (B7).
• the compound represented by formula (B18) (hereinafter referred to as compound (B18)) is obtained by reacting the compound represented by formula (B27) (hereinafter referred to as compound (B27)) and compound (M12) in the presence of a base.
• a step of reacting to obtain a compound represented by formula (B17) (hereinafter referred to as compound (B17)) (hereinafter referred to as step (3-1)), and compound (B17) and compound (M10) with a base It can be produced by a step of reacting in the presence of (hereinafter referred to as step (3-2)).
• step (3-2) the symbols have the same meanings as described above. ]
• the step (3-1) can be carried out according to the step (K-1) of the manufacturing method K, using the compound (B27) instead of the compound (B26).
• the step (3-2) can be carried out according to the step (K-2) of the manufacturing method K, using the compound (B17) instead of the compound (B9).
• Reference manufacturing method 4 Compound (B2) can be produced by reacting compound (B1) with diboronic acid or diboronic acid ester in the presence of a base and a palladium catalyst.
• the reaction is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; Nitriles and mixtures of two or more thereof are included.
• bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, acetates, and tripotassium phosphate.
• Palladium catalysts include, for example, PdCl 2 (dppf).
• Diboronic acids or diboronic acid esters include bis(pinacolato)diboron, tetrahydroxydiborane, and the like.
• the ratio of diboronic acid or diboronic ester is usually 1 to 5 mol
• the ratio of base is usually 1 to 5 mol
• the palladium catalyst is usually 0.01 to 0.5. Used in molar proportions.
• the reaction temperature is generally within the range of 0 to 150° C.
• the reaction time is generally within the range of 0.1 to 48 hours.
• the compound (B2) can be isolated by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
• Reference manufacturing method 5 Compound (B5) can be produced by oxidizing compound (B2).
• the reaction is usually carried out in a solvent.
• Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water and mixtures of two or more thereof.
• the oxidizing agent used for the reaction include meta-chloroperbenzoic acid and hydrogen peroxide solution.
• a base may be added as necessary. Bases include sodium hydroxide and potassium hydroxide.
• the oxidizing agent is generally used in a proportion of 1 to 5 mol per 1 mol of compound (B2).
• the base is usually used in a proportion of 0.1 to 5 mol per 1 mol of compound (B2).
• the reaction temperature is generally in the range of -20 to 120°C, and the reaction time is generally in the range of 0.1 to 48 hours.
• water and a reducing agent such as sodium thiosulfate are added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentrating the organic layer are performed to isolate compound (B5). can do.
• the compound (B5) is obtained by reacting a compound represented by the formula (B19) (hereinafter referred to as compound (B19)) with a diboronic acid or a diboronic acid ester in the presence of a base and a palladium catalyst to obtain a compound represented by the formula (B20).
• a step of obtaining a compound (hereinafter referred to as compound (B20)) (hereinafter referred to as step (6-1)), and compound (B20) and compound (M13) are reacted in the presence of a base and a metal catalyst. It can be produced by a process (hereinafter referred to as process (6-2)).
• process (6-2) In the formula, the symbols have the same meanings as described above. ]
• Step (6-1) can be carried out according to Reference Production Method 4 using compound (B19) instead of compound (B1).
• Compound (B19) is a known compound, or can be produced according to a known method.
• Step (6-2) can be carried out according to production method A using compound (B20) instead of compound (M1) and compound (M13) instead of compound (B1).
• the compound represented by formula (B21) (hereinafter referred to as compound (B21)) can be produced by reacting compound (B5) with trifluoroacetic anhydride in the presence of a base.
• a solvent Solvents used in the reaction include, for example, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more thereof.
• bases include organic bases.
• trifluoroacetic anhydride is generally used in an amount of 1 to 10 mol
• the base is generally used in an amount of 1 to 10 mol, per 1 mol of compound (B5).
• the reaction temperature is usually within the range of -20 to 100°C.
• the reaction time is usually within the range of 0.1 to 48 hours.
• the compound represented by formula (B22) can be produced by reacting compound (B1) with a compound represented by formula (M15) (hereinafter referred to as compound (M15)).
• compound (M15) a compound represented by formula (M15)
• R 57 represents a methyl group or an ethyl group, and other symbols have the same meanings as above.
• the reaction can be carried out, for example, according to the method described in WO2016/123253.
• Compound (M15) is a commercially available compound, or can be produced according to a known method.
• Reference manufacturing method 9 Compound (B4) can be produced by reacting compound (B3) with hydroxylamine or a salt thereof.
• Salts of hydroxylamine include, for example, hydrochlorides and sulfates. The reaction can be carried out according to production method D using hydroxylamine or a salt thereof instead of compound (M4).
• Reference manufacturing method 10 A compound represented by formula (B23) can be produced by reacting compound (B1) with N-formylsaccharin in the presence of a palladium catalyst, a ligand, triethylsilane and a base. [In the formula, symbols have the same meanings as described above. ] The reaction is described in Angew. Chem. Int. Ed. , 2013, 52, 8611-8615 and the like.
• Reference manufacturing method 11 A compound represented by formula (B24) can be produced by reacting compound (B27) with compound (M1) in the presence of a palladium catalyst and a base. [In the formula, symbols have the same meanings as described above. ]
• reaction can be carried out according to production method A using compound (B27) instead of compound (B1).
• Reference manufacturing method 12 A compound represented by formula (B25) can be produced by reacting compound (B27) with compound (M3) in the presence of a metal catalyst and a base. [In the formula, the symbols have the same meanings as described above. ]
• reaction can be carried out according to production method C using compound (B27) instead of compound (B1).
• the compound of the present invention can be mixed or used in combination with one or more components (hereinafter referred to as the present component) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below. can be done.
• the mixed use or combined use means using the compound of the present invention and this component at the same time, separately or with a time interval.
• the compound of the present invention and the component of the present invention may be contained in separate formulations or may be contained in one formulation.
• composition A One aspect of the present invention is one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (that is, the present component), and the compound of the present invention It is a composition containing (hereinafter referred to as composition A).
• Group (a) includes acetylcholinesterase inhibitors (e.g. carbamate insecticides, organophosphorus insecticides), GABAergic chloride ion channel blockers (e.g. phenylpyrazole insecticides), sodium channel modulators (e.g. pyrethroid insecticides).
• acetylcholinesterase inhibitors e.g. carbamate insecticides, organophosphorus insecticides
• GABAergic chloride ion channel blockers e.g. phenylpyrazole insecticides
• sodium channel modulators e.g. pyrethroid insecticides.
• nicotinic acetylcholine receptor competitive modulators e.g., neonicotinoid insecticides
• nicotinic acetylcholine receptor allosteric modulators glutamatergic chloride channel allosteric modulators (e.g., macrolide insecticides)
• nereistoxin insecticides chitin synthesis inhibitors, moulting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III and IV, voltage dependent from sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal modulators, microbial insecticides, and other insecticidal, acaricidal and nematicidal active ingredients. It is a group of They are described in the IRAC mechanism-based classification.
• Group (b) includes nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeletal inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides).
• nucleic acid synthesis inhibitors e.g., phenylamide fungicides, acyl amino acid fungicides
• cell division and cytoskeletal inhibitors e.g., MBC fungicides
• respiratory inhibitors e.g., QoI fungicides
• QiI fungicides amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyridine-based fungicides), signal transduction inhibitors, lipid and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMIs such as triazoles) fungicides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides, and other fungicidal active ingredients. They are described in the FRAC mechanism-based classification.
• Group (c) is a group of plant growth-regulating components (including mycorrhizal fungi and rhizobia).
• Group (d) is a group of repellent ingredients.
• alanycarb + SX means the combination of alanycarb and SX.
• the abbreviation SX means any one compound of the present invention selected from the group of compounds SX1 to SX259 described in Examples.
• all of the components described below are known components and can be obtained from commercially available formulations or produced by known methods. If this component is a microorganism, it can also be obtained from a bacteria depository.
• the numbers in parentheses represent CAS RN (registered trademark).
• a combination of this component of group (a) above and a compound of the present invention abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acynonapyr + SX, aphidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha endosulfan -endosulfan + SX, aluminum phosphide + SX, amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos- methyl) + SX, azocyclotin + SX, bark of Celastrus angulatus + SX, bendi
• Kurstaki strain HD-1 + SX Bacillus Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var.
• japonensis strain buibui + SX Bacillus thuringien sis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var.
• pumilus strain AQ717 + SX Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB/BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002/AQ30002 + SX, Bacillus subtilis strain QST30004/AQ30004 + SX, Bacillus subtilis strain QST71
• the ratio of the compound of the present invention to the component is not particularly limited, but the weight ratio (compound of the present invention:the component) is 1000:1 to 1:1000, 500:1 to 1:500, 100:1. ⁇ 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1 : 1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc. .
• the compound of the present invention has efficacy against pests.
• pests include phytopathogenic microorganisms, harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks.
• the compound of the present invention can control plant diseases caused by phytopathogenic microorganisms such as fungi, Oomycete, Phytomyxea, and bacteria.
• Fungi include, for example, Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota and Olpidiomycota. Specifically, the following are mentioned, for example. Parentheses indicate the scientific name of the phytopathogenic microorganism that causes each disease.
• Rice diseases Pyricularia oryzae, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi, Sclerophthora macrospora, Sclerophthora macrospora, and Epicoccum nigrum, Trichoderma viride, Rhizopus oryzae, pseudocolonial blight (Waitea circinata, Ceratobasidium setariae, Thanatephorus cucumeris)); Wheat diseases: Powdery mildew (Blumeria graminis), Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale, Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Red rust (Puccinia recondita) ), red snow rot (Microdochium nivale, Microdochium majus), snow rot (Typhula
• Polymyxa betae and Polymyxa graminis Diseases caused by bacteria: Burkholderia plantarii of rice, Pantoea ananatis of rice, Xanthomonas oryzae pv. oryzae. of rice, bacterial spot of cucumber (Pseudomonas syringae pv.
• harmful arthropods examples include the following.
• Hemiptera Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes orizicolus, etc.
• Delphacidae Leafhopper (Nephotettix cincticeps), Leafhopper (Nephotettix virescens), Leafhopper (Nephotettix nigropictus), Leafhopper (Recilia dorsalis), Leafhopper (Empoasca onukii), Potato Leafhopper (Empoasca fabae) , Corn leaf hopper (Dalbulus maidis), White leafhopper (Cofana spectra), Amrasca biguttula biguttula, etc. Cicadellidae; European Spittle Bug (Philaenus spumarius), etc.
• Aphis fabae Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Green peach aphid ( Myzus persicae), Brachycaudus helichrysi, Brevicoryne brassicae, rosy apple aphid (Dysaphis plantaginea), Lipaphis erysimi, Macrosiphum euphorbiae, potato aphid Aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat neck aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus aphid (Toxoptera citricida), peach aphid (Hyalopterus pruni), hienoaphis (Melanaphis) sacchari), Tetraneura nigriabdominal
• Aphididae such as Daktulosphaira vitifoliae, Phylloxera devastatrix, Phylloxera notabilis, and Phylloxera russelae; Adelges tsugae, balsam woolly Adelgidae such as Aphid (Adelges piceae), Aphrastasia pectinatae; stink bug (Eysarcoris aeneus), stink bug (Eysarcoris lewisi), stink bug (Eysarcoris ventralis), stink bug (Eysarcoris annamita), brown stink bug (Halyomorpha halys), green stink bug (Nezara viridula), brown stink bug ( Euschistus heros), red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus, etc.; Pentatomidae; Scaptocoris castanea
• Lepidoptera Chilo suppressalis, Chilo polychrysus, White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis, Rice hare moth (Marasmia exigua), cotton moth (Notarcha derogata), corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), high spotted moth (Hellula undalis), monkey crocodile moth (Herpetogramma luctuosale), Shibatutoga (Parapediasia teterrellus) , Rice case worm (Nymphula depunctalis), Sugar cane borer (Diatraea saccharalis), Egg plant fruit borer (Leucinodes orbonalis), etc.; Pyralidae such as Euzophera
• Heliothis virescens such as Heliothis virescens, Helicoverpa spp. such as Helicoverpa armigera and Helicoverpa zea, Velvet bean caterpillar (Anticarsia gemmatalis), Cotton leaf worm (Alabama argillacea), Hop wine borer (Hydraecia immanis) and other noctuids (Noctuidae); Pieridae such as Pieris rapae; orana fasciata), Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Epinotia aporema Tortricidae, such as , Citripestis sagittiferella, European grape wine moss (Lobesia botrana); Gracilariidae such as Caloptilia theivora and Phyllonorycter ringoniella;
• Plutellidae such as Plutella xylostella
• Gelechiidae such as Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, and Tuta absolutea
• Arctiidae such as (Hyphantria cunea); Castniidae, such as giant sugar cane borer (Telchin licus); Cossidae, such as Cossus insularis
• Geometridae such as Ascotis selenaria Geometridae
• Limacodidae such as Parasa lepida
• Stathmopodidae such as Stathmopoda Stammssa
• Hesperiidae such as Parnara gut
• Thysanoptera Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips , Echinothrips americanus, Scirtothrips perseae, etc.; Phlaeothripidae, such as Haplothrips aculeatus.
• Anthomyiidae such as Delia platura, Delia antiqua, and Pegomya cunicularia
• Ulidiidae such as Tetanops myopaeformis Agromyzidae, such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola
• Chloropidae such as Chlorops oryzae
• Bactrocera cucurbitae Bactrocera dorsalis, Bactrocera latifrons, Bactrocera oleae, Bactrocera tryoni, Ceratitis capitata, Rhagoletis pomonella, Rjapachla fruit fly ), etc.
• Drosophilidae such as Drosophila melanogaster
• Phoridae such as Megaselia spiracularis
• Psychodidae such as Clogmia albipunctata
• Culicidae such as Prosimulium yezoensis and Simulium ornatum
• Tabanidae such as Tabanus trigonus
• Musca domestica and Muscinasta bulans marbling Muscidae such as Stomoxys calcitrans and Haematobia irritans
• Calliphoridae Sarcophagidae
• Chironomus plumosus Chironomus yoshimatsui
• Glyptotendipes tokunagai of Chironomidae Chironomidae
• Diabrotica spp. e.g. Western Corn Rootworm (Diabrotica virgifera virgifera), Southern Corn Rootworm (Diabrotica undecimpunctata howardi), Northern Corn Rootworm (Diabrotica barberi), Mexican Corn Rootworm (Diabrotica virgifera zeae)), banded cucumber beetle (Diabrotica balteata), cucumber beetle (Diabrotica speciosa) and other bean leaf beetles (Cerotoma trifurcata), neck beetle (Oulema melanopus), cucumber beetle (Aulacophora femoralis), cucumber beetle (Phyllotreta striolata), cabbage-free beetle (Phyllotreta cruciferae), western black-free beetle (Phyllotreta pusilla), cabbage stem-free beetle (Psylliodes chrysocephala), hop-free bee
• Tenebrionidae such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus; Coccinellidae, such as Epilachna vigintioctopunctata; Lyctus brunneus, Rhizopertha dominica, etc.; Ptinidae; Ptinidae; Anoplophora malasiaca, Migdolus fryanus, Aromia bungii, etc.; Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., Limonius Limonius spp., Aeolus spp., Elateridae; Paederus fuscipes, Staphylinidae; Anthrenus verbasci, Dermestes maculates ), Trogoderma granarium, etc.
• Hymenoptera Tenthredinidae, such as Athalia rosae and Athalia japonica; Solenopsis spp., such as Solenopsis invicta and Solenopsis geminata, brown leaf-cutting ants (Atta capiguara), Acromyrmex spp., Paraponera clavata, Ochetellus glaver, Monomorium pharaonis, Linepithema humile , Formica japonica, Pristomyrmex punctutus, Pheidole noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, etc., Camponotus spp.
• Pogonomyrmex spp. such as Pogonomyrmex occidentalis, Wasmania spp. such as Wasmania auropunctata, Formicidae such as Anoplolepis gracilipes; Vespa mandarinia ), Vespa simillima, Vespa analis, Vespa velutina, Polistes jokahamae, etc.; Siricidae, such as Urocerus gigas ; Bethylidae.
• Blattodea Ectobiidae, such as Blattella germanica; Blatta orientalis); Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis, Reticulitermes amamianus, Reticutermes miyatakei), Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.
• Siphonaptera Pulicidae, such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, and Echidnophaga gallinacea; Hectopsyllidae, such as penetrans; Ceratophyllidae, such as the European rat flea (Nosopsyllus fasciatus).
• Pulicidae such as Pulex irritans, Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, and Echidnophaga gallinacea
• Hectopsyllidae such as penetrans
• Ceratophyllidae such as the European rat flea (Nosopsyllus fasciatus).
• Psocodae Pediculidae, such as head lice (Pediculus humanus capitis); Pthiridae, such as pubic lice (Pthirus pubis); Haematopinidae); Linognathidae, such as Linognathus vituli, Linognathus ovillus, Solenopotes capillatus; Bovicola bovis, Bovicola forvis, Bovicola breviceps, Damalin Bovicoliidae, such as Werneckiella spp.; Trichodectidae, such as Trichodectes canis and Felicola subrostratus; Menopon gallinae, Menacanthus stramineus ), Menoponidae such as Trinoton spp.; Trimenoponidae such as Cummingsia spp.; Trogiidae such as Trogium pulsatorium; Liposcelidae or Liposcelidida
• Thysanura Lepismatidae, such as Ctenolepisma villosa and Lepisma saccharina.
• Araneae Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii.
• Polydesmida Paradoxosomatidae, such as Oxidus gracilis and Nedyopus tambanus.
• Isopoda Armadillidiidae, such as Armadillidium vulgare.
• Chilopoda Scutigeridae, such as Thereuonema hilgendorfi; Scolopendridae, such as Scolopendra subspinipes; Ethopolyidae, such as Bothropolys rugosus.
• Gastropoda Limacidae, such as Limax marginatus and Limax flavus; Philomycidae, such as Meghimatium bilineatum; Pomacea canaliculata, etc. Lymnaeidae, such as Austropeplea ollula.
• Nematoda Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchidae; Meloidogyne javanica, Meloidogyne incognita, guava root-knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, Heterodera glycines, potato cyst nematode ( Heteroderidae such as Globodera rostochiensis and Globodera pallida; Hoplolimidae such as Rotylenchus reniformis; Anguinidae); Tylenchulidae, such as citrus nematode (Tylenchulus semipenetrans); Longidoridae, such as Xiphinema index; Trichodoridae; Aphelenx family (Parasitaphelenchidae).
• Harmful insects, harmful arthropods such as harmful mites, harmful molluscs and harmful nematodes have reduced drug sensitivity or drug resistance to insecticides, acaricides, molluscicides and nematicides. It may be developed harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes.
• an effective amount of the compound of the present invention or composition A is applied directly to pests and/or to habitats of pests (plants, soil, indoors, animals, etc.). It is done by Examples of the pest control method of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoking treatment, water surface treatment and seed treatment.
• the compound or composition A of the present invention is usually prepared by mixing an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier with a surfactant or the like, and optionally adding a binder, a dispersant, a stabilizer, or the like for formulation.
• solid carriers examples include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice stone, silica sand, chemical fertilizers. fine powders and granules of (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.) and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).
• clay pyrophyllite clay, kaolin clay, etc.
• talc calcium carbonate
• diatomaceous earth zeolite
• bentonite acid clay
• attapulgite white carbon
• ammonium sulfate vermiculite
• perlite perlite
• pumice stone pumice
• liquid carriers examples include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methyl naphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides ( N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethylsulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic
• gaseous carriers examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.
• surfactants examples include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkylsulfonates, alkylarylsulfonates , alkyl sulfates, etc.).
• formulation adjuvants include binders, dispersants, colorants, stabilizers, etc.
• Specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, Examples include water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acidic isopropyl phosphate, and dibutylhydroxytoluene.
• an adjuvant can be used as a component that enhances or assists the efficacy of the compound of the present invention.
• plants include whole plants, foliage, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs and seedlings.
• the vegetative reproductive organ means the plant's roots, stems, leaves, etc. that have the ability to grow when the part is separated from the main body and placed in the soil.
• Vegetative reproductive organs include, for example, tuberous root, creeping root, bulb, corm or solid bulb, tuber, rhizome, stolon , rhizophore, cane cuttings, propagule and vine cuttings.
• the stolons are sometimes called runners, and the mukago is also called buds, which are divided into broad buds and bulbils.
• a vine means a shoot (collective term for leaves and stems, shoot) of sweet potato, yamanoimo, and the like. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores or tuberous roots are collectively called bulbs. Cultivation of potatoes begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.
• an effective amount of the compound of the present invention or composition A is applied to soil before or after planting plants. and the method of applying. More specifically, for example, planting hole treatment (planting hole spraying, planting hole treatment soil mixing), stock base treatment (stock base spraying, stock base soil mixing, stock irrigation, late seedling period stock base treatment), planting groove Treatment (ditch spraying, ditch soil mixing), cropping treatment (cropping spraying, cropping soil mixing, growing season cropping), cropping treatment at the time of sowing (crop spraying at the time of sowing, cropping soil mixing at the time of sowing) ), full surface treatment (overall soil spraying, full soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spraying treatments (granule spraying during the growing season, foliar spraying, under the canopy or around the trunk) , soil surface spraying, soil surface mixing, sowing hole spraying, furrow ground surface spray
• Seed treatment includes, for example, the treatment of seeds or vegetative reproductive organs with the compound of the present invention or composition A. Specifically, for example, a suspension of the compound of the present invention or composition A is atomized and applied to the seed surface. Alternatively, a spraying treatment in which the surface of the vegetative reproductive organs is sprayed, a smearing treatment in which the compound of the present invention or composition A is applied to seeds or vegetative reproductive organs, and an immersion treatment in which seeds are immersed in a chemical solution of the compound of the present invention or composition A for a certain period of time. , a method of coating seeds or vegetative reproductive organs with a carrier containing the compound of the present invention or composition A (film coating, pellet coating, etc.).
• the vegetative and reproductive organs mentioned above include, in particular, seed potatoes.
• the seed or the vegetative reproductive organ can be treated with the composition A as a single formulation, or the composition A can be divided into a plurality of different formulations and applied to the seeds. Alternatively, it can be processed into vegetative and reproductive organs.
• a method of treating composition A in a plurality of times as different formulations for example, a formulation containing only the compound of the present invention as an active ingredient is treated, seeds or vegetative reproductive organs are air-dried, and then this component is added.
• the seed or vegetative reproductive organ retaining the compound of the present invention or composition A in the present invention means a state in which the compound of the present invention or composition A is attached to the surface of the seed or vegetative reproductive organ. .
• the seed or vegetative reproductive organ holding the compound of the present invention or composition A described above is treated with a compound other than the compound of the present invention or composition A before or after the compound of the present invention or composition A is attached to the seed or vegetative reproductive organ. Materials may be attached.
• the layer when the composition A adheres to the surface of a seed or vegetative reproductive organ in a layer, the layer consists of one layer or multiple layers. Also, when it consists of a plurality of layers, each layer is a layer containing one or more active ingredients, or a layer containing one or more active ingredients and a layer not containing an active ingredient. Become. Seeds or vegetative reproductive organs retaining the compound of the present invention or composition A are obtained, for example, by applying a formulation containing the compound of the present invention or composition A to seeds or vegetative reproductive organs by the method of seed treatment described above. be able to.
• the application rate is generally 1-10000 g of the compound of the present invention per 10000 m 2 .
• the amount of the compound of the present invention is usually applied in the range of 0.001 to 100 g per 1 kg of seeds or vegetative reproductive organs.
• the compound of the present invention or composition A is formulated as an emulsion, wettable powder, flowable powder, etc., it is usually applied after being diluted with water so that the concentration of the active ingredient is 0.01 to 10000 ppm. Agents, powders and the like are usually applied as they are.
• It can also be treated by wrapping a sheet-shaped or string-shaped resin formulation around crops, spreading it around crops, or laying it on the soil at the base of the plant.
• the amount of application is the amount of the compound of the present invention per 1 m 2 of the treated area when the surface is treated.
• the amount is 0.01 to 1000 mg
• the amount of the compound of the present invention per 1 m 3 of space to be treated is usually 0.01 to 500 mg.
• the compound of the present invention or composition A is formulated as an emulsion, wettable powder, flowable preparation, etc., it is usually diluted with water so that the concentration of the active ingredient is 0.1 to 10,000 ppm before application. , aerosol agents, fumigants, poison baits, etc. are applied as they are.
• composition A When the compound of the present invention or composition A is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats, chickens, etc., and small animals such as dogs, cats, rats, mice, etc., veterinary known methods are used. Can be used on animals with As a specific method of use, for the purpose of systemic suppression, for example, it is administered by tablet, feed, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and non-systemic suppression is intended.
• systemic suppression for example, it is administered by tablet, feed, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), and non-systemic suppression is intended.
• the amount of the compound of the present invention or composition A when administered to an animal is generally in the range of 0.1-1000 mg per kg body weight of the animal.
• the compound or composition A of the present invention can be used as a pest control agent in agricultural lands such as fields, paddy fields, lawns, and orchards. Examples of plants include the following.
• the plant is not particularly limited as long as it is a variety that is generally cultivated.
• the above plants also include plants that can be produced by natural crossing, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops.
• genetically modified crops include HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, and EPSP (5 - enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or plants that have been made tolerant to herbicides such as dicamba ; Plants capable of synthesizing selective toxins, etc.
• HPPD 4-hydroxyphenylpyruvate dioxygenase
• ALS acetolactate
• RNAi gene silencing
• Me represents a methyl group
• Et represents an ethyl group
• Pr represents a propyl group
• i-Pr represents an isopropyl group
• Bu represents a butyl group
• i-Bu represents an isobutyl group.
• t-Bu represents a tert-butyl group
• Pen represents a pentyl group
• c-Pr represents a cyclopropyl group
• c-Bu represents a cyclobutyl group
• c-Pen represents a cyclopentyl group
• c-Hex represents a cyclohexyl group
• Ph represents a phenyl group.
• LCMS liquid chromatography/mass spectrometry
• MS mass spectrometry
• Reference production example 2 A mixture of 1.0 g of intermediate 1-5, 1.1 g of bis(pinacolato)diboron, 0.24 g of PdCl 2 (dppf), 0.66 g of tripotassium phosphate, and 30 mL of dimethoxyethane was prepared at 80° C. under a nitrogen atmosphere. Stirred for 6 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 1.0 g of Intermediate 2-1 represented by the following formula.
• Reference production example 3 A mixture of 2.0 g of intermediate 1-5, 0.47 g of bis(triphenylphosphine)palladium(II) dichloride, 4.4 mL of tributyl(1-ethoxyvinyl)tin and 20 mL of 1,4-dioxane was added under a nitrogen atmosphere. at 110° C. for 4 hours. 1N Hydrochloric acid was added to the resulting mixture, and the mixture was stirred at room temperature for 1 hour. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
• Reference Production Example 5-1 The compounds produced according to Reference Production Example 5 and their physical properties are shown below.
• Reference Production Example 7-1 The compounds produced according to Reference Production Example 7 and their physical properties are shown below.
• Production Example 1-1 The compounds produced according to Production Example 1 and their physical properties are shown below.
• Formula (1-1) wherein R 1 , R 2a , R 2b , R 3 , R 4 , X and L are any combination described in [Table A4].
• Invention compound 1-4 1 H-NMR (CDCl 3 ) ⁇ : 7.58 (1H, s), 7.33-7.27 (2H, m), 7.25-7.21 (2H, m), 7.13 (1H, s), 7.09 (1H, s), 7.02-6.98 (1H, m), 3.83 (3H, s), 3.71 (3H, s), 2.43 (3H, s), 2.39 (3H, s), 2.18 (3H, s).
• Invention compound 1-8 1 H-NMR (CDCl 3 ) ⁇ : 8.35 (1H, s), 7.56 (1H, s), 7.43-7.40 (2H, m), 7.38-7.30 (4H, m), 7.05 (1H, s), 5.19 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.36 (3H, s), 2.15 (3H, s).
• Production example 2 0.10 g of intermediate 1-5, 0.02 g of PdCl 2 (PPh 3 ) 2 , 0.15 mL of cyclopropylacetylene, 1.0 mL of tetrabutylammonium fluoride (1 mol/L THF solution) under nitrogen atmosphere, and 3 mL of THF was stirred at 80° C. for 6 hours. Aqueous sodium bicarbonate was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure.
• Production example 2-1 The compounds produced according to Production Example 2 and their physical properties are shown below.
• Production example 3 A mixture of 0.18 g of intermediate 4-1, 0.06 mL of butanol, 0.13 g of bis(2-methoxyethyl) azodicarboxylate, 0.13 g of triphenylphosphine, and 4 mL of chloroform was stirred at room temperature for 4 hours. . Aqueous sodium bicarbonate was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
• Production Example 3-1 The compounds produced according to Production Example 3 and their physical properties are shown below.
• Formula (3-1) wherein R 1 , R 2a , R 2b , R 6 , X and L are any combination described in [Table A5].
• Production Example 4-1 The compounds produced according to Production Example 4 and their physical properties are shown below.
• Formula (4-1) wherein R 1 , R 2a , R 2b , R 3a , R 4a , R 5a , R 6a , R 7a , X and L are any combination described in [Table A6].
• Invention compound 4-8 1 H-NMR (CDCl 3 ) ⁇ : 7.35-7.29 (3H, m), 7.23-7.19 (1H, m), 7.17 (1H, s), 6.96 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.26 (3H, s), 2.20 (3H, s).
• Compound 4-9 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.34-7.28 (1H, m), 7.17 (1H, s), 7.00 (1H, s), 6.93-6.86 (3H, m), 4.07 (3H, s), 3.87 (3H, s), 3.82 (3H, s), 2.28 (3H, s), 2.20 (3H, s).
• Invention compound 4-10 1 H-NMR (CDCl 3 ) ⁇ : 7.45-7.39 (1H, m), 7.28-7.25 (1H, m), 7.21-7.17 (3H, m), 6.98 (1H, s) , 4.07 (3H, s), 3.88 (3H, s), 2.27 (3H, s), 2.21 (3H, s).
• Compound 4-11 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.61-7.57 (2H, m), 7.53-7.50 (2H, m), 7.21-7.19 (1H, m), 6.98 (1H, s) , 4.07 (3H, s), 3.88 (3H, s), 2.26 (3H, s), 2.21 (3H, s).
• Compound 4-12 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.41-7.28 (5H, m), 7.16 (1H, s), 6.99 (1H, s), 6.78 (1H, s), 3.97 (3H , s), 2.93 (3H, d), 2.26 (3H, s), 2.20 (3H, s).
• Invention compound 4-13 1 H-NMR (CDCl 3 ) ⁇ : 7.34-7.32 (1H, m), 7.31-7.27 (2H, m), 7.23-7.20 (1H, m), 7.15 (1H, s) , 6.95 (1H, s), 6.79 (1H, br s), 3.98 (3H, s), 2.93 (3H, d), 2.25 (3H, s), 2.19 (3H, s).
• Invention compound 4-15 1 H-NMR (CDCl 3 ) ⁇ : 7.57 (1H, s), 7.31-7.25 (1H , m), 7.17-7.10 (4H, m), 7.00 (1H, s), 3.82 (3H, s), 3.71 (3H, s), 2.38 (3H, s), 2.26 (3H, s), 2.19 ( 3H, s).
• Invention compound 4-18 1 H-NMR (CDCl 3 ) ⁇ : 7.58 (1H, s), 7.37-7.31 (1H, m), 7.16-7.10 (2H, m), 7.08-6.97 (3H, m), 3.84 (3H, s), 3.71 (3H, s), 2.25 (3H, s), 2.20 (3H, s).
• Invention compound 4-25 1 H-NMR (CDCl 3 ) ⁇ : 7.57 (1H, s), 7.47-7.27 (6H, m), 7.13 (1H, s), 7.00 (1H, s), 6.97-6.92 (3H, m), 5.08 (2H, s), 3.82 (3H, s), 3.71 (3H, s), 2.21 (3H, s), 2.19 (3H, s).
• Production example 5 A mixture of 0.18 g of intermediate 2-1,2-bromo-3-fluoropyridine 0.09 mL, PdCl 2 (dppf) 0.02 g, tripotassium phosphate 0.24 g, dimethoxyethane 4 mL and water 1 mL under a nitrogen atmosphere. The mixture was stirred at 80° C. for 8 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
• Production Example 5-1 The compounds produced according to Production Example 5 and their physical properties are shown below.
• Formula (5-1) wherein R 1 , R 2a , R 2b , E b , X and L are any combination described in [Table B2]. ( ⁇ represents the bonding site with the benzene ring.)
• Compound 5-2 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.89 (1H, t), 7.63-7.57 (3H, m), 7.19 (1H, s), 7.17 (1H, s), 3.83 (3H , s), 3.70 (3H, s), 2.40 (3H, s), 2.20 (3H, s).
• Compound 5-3 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.18 (1H, s), 7.13 (1H, d), 7.01 (1H, s), 6.90 (1H, d), 4.07 (3H, s ), 3.87 (3H, s), 2.22 (3H, s), 2.20 (3H, s).
• Compound 5-4 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.18 (1H, s), 7.13 (1H, d), 7.01 (1H, s), 6.90 (1H, d), 4.07 (3H, s ), 3.87 (3H, s), 2.22 (3H, s), 2.20 (3H, s).
• Compound 5-5 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.87 (1H, s), 7.84 (1H, s), 7.58 (1H, s), 7.16 (1H, s), 7.07 (1H, s ), 3.84 (3H, s), 3.72 (3H, s), 2.35 (3H, s), 2.18 (3H, s).
• Production example 6 A mixture of 0.10 g of intermediate 1-5, 0.08 g of 1-cyclopentenylboronic acid, 0.02 g of PdCl 2 (dppf), 0.21 g of tripotassium phosphate, 4 mL of dimethoxyethane and 1 mL of water under nitrogen atmosphere. Stir at 80° C. for 6 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
• Production Example 6-1 The compounds produced according to Production Example 6 and their physical properties are shown below.
• Combination A consists of substituent numbers ZA1 to ZA364.
• Substituent numbers ZA1 to ZA364 represent the combination of R 3 and R 4 in compound (1A), and are hereinafter referred to as [substituent numbers; R 3 , R 4 ].
• Substituent Number ZA2 means a combination in which R3 is an ethyl group and R4 is a hydrogen atom.
• X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is an ethyl group, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX2).
• compound group SX2 is a fluorine atom
• R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX3).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a chlorine atom, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX4).
• compound (1A) is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a methoxy group, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX5).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a cyclopropyl group, and R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX6).
• compound (1A) is CH, L is an oxygen atom, R 1 is a fluorine atom, R X22 is a methyl group, and R 3 and R 4 are any combination described in combination A (hereinafter referred to as compound group SX7).
• X is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a fluorine atom, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX8).
• compound (1A) is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a chlorine atom, and R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX9).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a methyl group, and R 3 and R 4 are any combination described in Combination A (hereinafter referred to as compound group SX10).
• compound group SX10 is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a fluorine atom, and R 3 and R 4 are any of combination A
• a compound that is a combination hereeinafter referred to as compound group SX11).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, and R 3 and R 4 are any of the combinations described in combination A.
• a compound that is a combination (hereinafter referred to as compound group SX12).
• compound group SX13 A compound that is a combination
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methyl group
• R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX13).
• compound (1A) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is an ethyl group, and R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX14).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a fluorine atom
• R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX15).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a chlorine atom
• R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX16).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methoxy group
• R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX17).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• R 3 and R 4 are any of combination A
• a compound that is a combination of hereinafter referred to as compound group SX18).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a methyl group
• R 3 and R 4 are any of combination A
• a compound that is a combination hereinafter referred to as compound group SX19.
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX20).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• R 3 and R 4 are any of the combinations A (hereinafter referred to as compound group SX21).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a methyl group
• R 3 and R 4 are any of combination A
• a compound that is a combination hereinafter referred to as compound group SX22).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX23).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R X2 is a chlorine atom
• R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX24).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a methyl group
• R 3 and R 4 are any of combination A A compound that is a combination
• SX25 a compound that is a combination
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is an ethyl group
• R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX26).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R X2 is a fluorine atom
• R 3 and R 4 are any of combination A A compound that is a combination
• SX27 a compound that is a combination
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a chlorine atom
• R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX28).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a methoxy group
• R 3 and R 4 are any of combination A
• a compound that is a combination hereinafter referred to as compound group SX29.
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• R 3 and R 4 are any of combinations A (hereinafter referred to as compound group SX30).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R x2 is a methyl group
• any combination of R 3 and R 4 described in combination A hereinafter referred to as compound group SX31.
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• R 3 and R 4 are any of combination A
• a compound that is a combination hereinafter referred to as compound group SX32).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R X2 is a chlorine atom
• R 3 and R 4 are any of combination A
• a compound that is a combination hereinafter referred to as compound group SX33.
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R x2 is a methyl group
• any combination of R 3 and R 4 described in combination A hereinafter referred to as compound group SX34).
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R X2 is a fluorine atom
• R 3 and R 4 are any of combination A A compound that is a combination
• SX35 a compound that is a combination
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R X2 is a chlorine atom
• R 3 and R 4 are any of combination A A compound that is a combination (hereinafter referred to as compound group SX36).
• Group V Me, Et, Pr, i-Pr, c-Pr, c-Bu, c-Pen, c-Hex, ( CH2 ) 3CH3 , CH2CH ( CH3 ) 2 , CH ( CH3 ) CH2CH3 , t-Bu,CH2c-Pr,( CH2 ) 4CH3 ,( CH2 )2CH ( CH3 ) 2 ,CH ( CH3 ) ( CH2 ) 2CH3 , CH ( CH2CH3 ) CH2CH3 , CH2CH ( CH3 ) CH2CH3 , C ( CH3 ) 2CH2CH3 , CH2t -Bu,CH2c - Bu, CH2c- Pen,( CH2 )2c-Pr,(1-methylcyclopropyl)methyl,( 2 -methylcyclopropyl)methyl,1-cyclopropylethyl,( CH2 ) 3c -Pr, ( CH2 ) 5CH3 ,(
• X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is an ethyl group, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX38).
• compound (1B) X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a fluorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX39).
• X is CH, L is an oxygen atom, R1 is a methyl group, R2 is a chlorine atom, and R5 is any substituent selected from group V.
• compound group SX40 Compound (hereinafter referred to as compound group SX40).
• compound (1B) X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a methoxy group, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX41).
• compound (1B) X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a cyclopropyl group, and R 5 is any substituent selected from group V;
• a certain compound hereinafter referred to as compound group SX42).
• compound (1B) X is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a fluorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX44).
• X is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a chlorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX45).
• compound group SX45 Compound (1B) wherein X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a methyl group, and R 5 is any substituent selected from Group V (hereinafter referred to as compound group SX46).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a fluorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX47).
• compound (1B) X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, and R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX48).
• X is a nitrogen atom, L is an oxygen atom, R1 is a methyl group, R2 is a methyl group, and R5 is any substituent selected from group V ;
• a certain compound hereinafter referred to as compound group SX49).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X2 is an ethyl group, and R 5 is any substituent selected from group V;
• a certain compound hereinafter referred to as compound group SX50).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X2 is a fluorine atom, and R 5 is any substituent selected from group V;
• a certain compound hereinafter referred to as compound group SX51).
• X is a nitrogen atom, L is an oxygen atom, R1 is a methyl group, R2 is a chlorine atom, and R5 is any substituent selected from group V ;
• a certain compound hereinafter referred to as compound group SX52).
• X is a nitrogen atom, L is an oxygen atom, R1 is a methyl group, R2 is a methoxy group, and R5 is any substituent selected from group V ;
• a certain compound hereinafter referred to as compound group SX53).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is a cyclopropyl group, and R 5 is any substituent selected from group V (hereinafter referred to as compound group SX54).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a methyl group
• R 5 is any substituent selected from group V.
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• R 5 is any substituent selected from group V
• a certain compound hereinafter referred to as compound group SX56).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R X2 is a chlorine atom
• R 5 is any substituent selected from group V
• SX57 A certain compound (hereinafter referred to as compound group SX57).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a methyl group
• R 5 is any substituent selected from group V.
• compound hereinafter referred to as compound group SX58).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a fluorine atom, and R 5 is any substituent selected from group V; A certain compound (hereinafter referred to as compound group SX59).
• compound (1B) X is a nitrogen atom, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, and R 5 is any substituent selected from group V
• X is a nitrogen atom, L is NH, R1 is a methyl group, R2 is a methyl group, and R5 is any substituent selected from group V.
• compound (1B) X is a nitrogen atom, L is NH, R1 is a methyl group, R2 is an ethyl group, and R5 is any substituent selected from group V.
• compound group SX62 Compound (hereinafter referred to as compound group SX62).
• compound (1B) X is a nitrogen atom, L is NH, R1 is a methyl group, R2 is a fluorine atom, and R5 is any substituent selected from group V.
• X is a nitrogen atom
• L is NH
• R1 is a methyl group
• R2 is a chlorine atom
• R5 is any substituent selected from group V.
• X is a nitrogen atom
• L is NH
• R1 is a methyl group
• R2 is a methoxy group
• R5 is any substituent selected from group V.
• X is a nitrogen atom
• L is NH
• R1 is a methyl group
• R2 is a cyclopropyl group
• R5 is any substituent selected from group V ;
• a certain compound hereinafter referred to as compound group SX66.
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX68).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R X2 is a chlorine atom
• R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX69).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a chlorine atom, and R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX75).
• compound (2B) X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a methoxy group, and R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX76).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x28 is a methyl group, and R 5 is any substituent selected from group V;
• a certain compound hereinafter referred to as compound group SX77).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X28 is a fluorine atom, and R 5 is any substituent selected from group V;
• a certain compound hereinafter referred to as compound group SX78).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x28 is a chlorine atom
• R 5 is any substituent selected from group V A certain compound (hereinafter referred to as compound group SX79).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a methyl group
• R 5 is any substituent selected from group V Compound (hereinafter referred to as compound group SX80).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a fluorine atom
• R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX81).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a chlorine atom
• R 5 is any substituent selected from group V compound (hereinafter referred to as compound group SX82).
• Group Y Et, Pr, i-Pr, ( CH2 ) 3CH3, CH2CH(CH3)2 , CH ( CH3 ) CH2CH3 , C( CH3 ) 3 , CH2c - Pr ,( CH2 ) 4CH3 ,( CH2 )2CH( CH3 ) 2 , CH ( CH3 ) ( CH2 ) 2CH3 ,CH ( CH2CH3 ) CH2CH3 , CH2CH ( CH3 ) CH2CH3 ,C( CH3 ) 2CH2CH3 ,CH2C(CH3)3 , CH2c - Bu , CH2c - Pen, CH2c - Hex,( CH2 ) 2c - Pr,(1-methylcyclopropyl)methyl,(2-methylcyclopropyl)methyl,1-cyclopropylethyl,( CH2 ) 3c -Pr,( CH2 ) 5CH3 ,( CH2 ) 3CH ( CH3 ) 2
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is an ethyl group, and R 6 is any substituent selected from group Y compound (hereinafter referred to as compound group SX84).
• compound group SX84 is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a fluorine atom, and R 6 is any substituent selected from group Y.
• compound SX85 compound (hereinafter referred to as compound group SX85).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a chlorine atom, and R 6 is any substituent selected from group Y.
• compound group SX86 Compound (hereinafter referred to as compound group SX86).
• compound group SX87 Compound (hereinafter referred to as compound group SX87).
• compound (1C) X is CH, L is an oxygen atom, R 1 is a methyl group, R X2 is a cyclopropyl group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX88).
• X is CH, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a fluorine atom, and R 6 is any substituent selected from group Y compound (hereinafter referred to as compound group SX90).
• compound (1C) is CH, L is an oxygen atom, R 1 is a fluorine atom, R x2 is a chlorine atom, and R 6 is any substituent selected from group Y.
• compound group SX91 Compound (hereinafter referred to as compound group SX91).
• compound group SX92 Compound (1C) wherein X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a methyl group, and R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX92).
• compound (1C) X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a fluorine atom, and R 6 is any substituent selected from group Y.
• compound group SX93 Compound (hereinafter referred to as compound group SX93).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, and R 6 is any substituent selected from group Y.
• compound group SX94 compound (hereinafter referred to as compound group SX94).
• compound (1C) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is a methyl group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX95).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is an ethyl group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX96).
• compound (1C) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X2 is a fluorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX97).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R X2 is a chlorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX98).
• compound (1C) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is a methoxy group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX99).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• R 6 is any substituent selected from group Y (hereinafter referred to as compound group SX100).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a methyl group
• R 6 is any substituent selected from group Y.
• Compound hereinafter referred to as compound group SX101).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a fluorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX102).
• compound (1C) X is a nitrogen atom, L is an oxygen atom, R 1 is a fluorine atom, R X2 is a chlorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX103).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a methyl group
• R 6 is any substituent selected from group Y.
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R X2 is a fluorine atom
• R 6 is any substituent selected from group Y
• a certain compound hereinafter referred to as compound group SX105).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R X2 is a chlorine atom
• R 6 is any substituent selected from group Y
• a certain compound hereinafter referred to as compound group SX106.
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a methyl group
• R 6 is any substituent selected from group Y.
• Compound hereinafter referred to as compound group SX107).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is an ethyl group
• R 6 is any substituent selected from group Y.
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a fluorine atom
• R 6 is any substituent selected from group Y.
• compound group SX109 Compound (hereinafter referred to as compound group SX109).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a chlorine atom
• R 6 is any substituent selected from group Y.
• compound group SX110 Compound (hereinafter referred to as compound group SX110).
• compound group SX111 Compound (hereinafter referred to as compound group SX111).
• compound (1C) X is a nitrogen atom, L is NH, R1 is a methyl group, R2 is a cyclopropyl group, and R6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX112).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• R 6 is any substituent selected from group Y.
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• R 6 is any substituent selected from group Y.
• compound group SX117 Compound (hereinafter referred to as compound group SX117).
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R x2 is a chlorine atom
• R 6 is any substituent selected from group Y.
• compound group SX118 Compound (hereinafter referred to as compound group SX118).
• Formula (2C) In the compound represented by (hereinafter referred to as compound (2C)), X is CH, L is an oxygen atom, R 1 is a methyl group, R is a methyl group, and m is 2 , R X3 , R X4 , R X5 , R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX119).
• Combination B consists of substituent numbers ZB1 to ZB306.
• Substituent numbers ZB1 to ZB306 are compound (2C), compounds represented by formula (1D), and combinations of R x3 , R x4 , R x5 , R x6 , and R x7 in compounds represented by formula (2D) and is hereinafter referred to as [substituent number; R X3 , R X4 , R X5 , R X6 , R X7 ].
• Substituent Number ZB2 means a combination in which R X3 is a methyl group and R X4 , R X5 , R X6 and R X7 are hydrogen atoms.
• X is CH
• L is an oxygen atom
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• m is 2, R X3 , R X4 , R X5 ,
• R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX120).
• X is CH
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• m is 2, R x3 , R x4 , R x5
• R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX121).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a fluorine atom, m is 2, R x3 , R x4 , R x5 , Compounds in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX122).
• compound group SX122 Compounds in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX122).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, m is 2, R X3 , R X4 , R X5 , A compound in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX123).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methyl group
• m is 3, R x3 , R x4 , R x5
• SX124 A compound in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX124).
• X is CH
• L is an oxygen atom
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• m is 3, R X3 , R X4 , R X5
• R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX125).
• X is CH
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• m is 3, R x3 , R x4 , R x5
• R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX126).
• X is CH
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• m is 3, R x3 , R x4 , R x5
• R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX127).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, m is 3, R X3 , R X4 , R X5 , Compounds in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX128).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a methyl group, m is 4, R x3 , R x4 , R x5 , A compound in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX129).
• X is CH
• L is an oxygen atom
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• m is 4, R X3 , R X4 , R X5 ,
• R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX130).
• X is CH
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• m is 4, R x3 , R x4 , R x5
• R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX131).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a fluorine atom, m is 4, R x3 , R x4 , R x5 , Compounds in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX132).
• compound group SX132 Compounds in which R X6 and R X7 are any combination described in combination B
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R X2 is a chlorine atom, m is 4, R X3 , R X4 , R X5 , A compound in which R X6 and R X7 are any combination described in combination B (hereinafter referred to as compound group SX133).
• Compound hereinafter referred to as compound group SX135).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a chlorine atom, and R 6 is any substituent selected from group Y Compound (hereinafter referred to as compound group SX136).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a methoxy group, and R 6 is any substituent selected from group Y Compound (hereinafter referred to as compound group SX137).
• X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x28 is a methyl group, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX138).
• compound (3C) X is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x28 is a fluorine atom, and R 6 is any substituent selected from group Y; A certain compound (hereinafter referred to as compound group SX139).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x28 is a chlorine atom
• R 6 is any substituent selected from group Y
• SX140 a certain compound
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a methyl group
• R 6 is any substituent selected from group Y
• compound group SX141 Compound
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a fluorine atom
• R 6 is any substituent selected from group Y.
• compound group SX142 Compound (hereinafter referred to as compound group SX142).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a chlorine atom
• R 6 is any substituent selected from group Y.
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is an ethyl group, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX145).
• compound group SX145 is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a fluorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX146).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a chlorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX147).
• compound (1D) is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a methoxy group, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX148).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x2 is a cyclopropyl group, and R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX149).
• compound (1D) is CH, L is an oxygen atom, R 1 is a fluorine atom, R x2 is a methyl group, and R x3 , R x4 , R x5 , R x6 and R x7 are combined A compound that is any combination described in B (hereinafter referred to as compound group SX150).
• X is CH, L is an oxygen atom, R 1 is a fluorine atom, R x2 is a fluorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX151).
• X is CH, L is an oxygen atom, R 1 is a fluorine atom, R x2 is a chlorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX152).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a methyl group, and R x3 , R x4 , R x5 , R x6 and R x7 are combined A compound that is any combination described in B (hereinafter referred to as compound group SX153).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a fluorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX154).
• X is CH, L is an oxygen atom, R 1 is a chlorine atom, R x2 is a chlorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX155).
• compound (1D) is a nitrogen atom, L is an oxygen atom, R 1 is a methyl group, R x2 is a methyl group, and R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX156).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is an ethyl group
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX157).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a fluorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX158).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a chlorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX159).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methoxy group
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX160).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a methyl group
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX162).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a fluorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX163).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX164).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a methyl group
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX165).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX166).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a chlorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX167).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a methyl group
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX168).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is an ethyl group
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX169).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a fluorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX170).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a chlorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX171).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a methoxy group
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX172).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX173).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R x2 is a methyl group
• R x3 , R x4 , R x5 , R x6 and R x7 are combined A compound that is any combination described in B (hereinafter referred to as compound group SX174).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R x2 is a fluorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX175).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX176).
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R x2 is a methyl group
• R x3 , R x4 , R x5 , R x6 and R x7 are combined A compound that is any combination described in B (hereinafter referred to as compound group SX177).
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX178).
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R x2 is a chlorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX179).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a fluorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX181).
• compound group SX182 is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a chlorine atom, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX182).
• X is CH, L is an oxygen atom, R 1 is a methyl group, R x28 is a methoxy group, and R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX183).
• compound group SX183 A compound that is any combination described in combination B
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x28 is a methyl group
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX184).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x28 is a fluorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX185).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x28 is a chlorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 is any combination described in combination B (hereinafter referred to as compound group SX186).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a methyl group
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX187).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a fluorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX188).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x28 is a chlorine atom
• R x3 , R x4 , R x5 , R x6 and R x7 are A compound that is any combination described in combination B (hereinafter referred to as compound group SX189).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R is a methyl group
• the structure of G and G wherein the substituents R x8 , R x9 , R x10 and R x11 corresponding to the structure of are any combination described in combination C (hereinafter referred to as compound group SX190 ).
• Combination C consists of substituent numbers ZC1-ZC1459.
• the substituent numbers ZC1 to ZC1459 represent the structure of G in the compound (1E) and the compound represented by the formula (2E) and the combination of the substituents R x8 , R x9 , R x10 and R x11 corresponding to the structure of G. hereinafter referred to as [substituent numbers; G, R X8 , R X9 , R X10 , R X11 ].
• Substituent Number ZC2 means a combination in which G is G1, R X8 is a methyl group, and R X9 , R X10 and R X11 are hydrogen atoms.
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is an ethyl group
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX191).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX192).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX193).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methoxy group
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX194).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX195).
• X is CH
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a methyl group
• the structure of G and the substituents R x8 and R corresponding to the structure of G Compounds in which X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX196).
• X is CH
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a methyl group
• the structure of G and the substituents R x8 and R corresponding to the structure of G Compounds in which X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX199).
• X is CH
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX200).
• X is CH
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX201).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methyl group
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX202).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is an ethyl group
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX203).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX204).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX205).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methoxy group
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX206).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R is a cyclopropyl group
• the structure of G and the substituent R corresponding to the structure of G Compounds in which X8 , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX207).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a methyl group
• the structure of G and the substituent R x8 corresponding to the structure of G, Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX208).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX209).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX210).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a methyl group
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX211).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX212).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a chlorine atom
• R is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX213).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a methyl group
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX214).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is an ethyl group
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX215).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G, Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX216).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX217).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a methoxy group
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX218).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX219).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R x2 is a methyl group
• the structure of G and the substituents R x8 and R corresponding to the structure of G Compounds in which X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX220).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G
• Compounds in which R X9 , R X10 and R X11 are any combination described in combination C hereinafter referred to as compound group SX221).
• X is a nitrogen atom
• L is NH
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G
• Compounds in which R X9 , R X10 and R X11 are any combination described in combination C hereinafter referred to as compound group SX222).
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R is a methyl group
• the structure of G and the substituents R x8 and R corresponding to the structure of G Compounds in which X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX223).
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G
• Compounds in which R X9 , R X10 and R X11 are any combination described in combination C hereinafter referred to as compound group SX224).
• X is a nitrogen atom
• L is NH
• R 1 is a chlorine atom
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX225).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R is a methyl group
• the structure of G and G wherein the substituents R x8 , R x9 , R x10 and R x11 corresponding to the structure of are any combination described in combination C (hereinafter referred to as compound group SX226 ).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX227).
• X is CH
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methoxy group
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX229).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a methyl group
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX230).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX231).
• X is a nitrogen atom
• L is an oxygen atom
• R 1 is a methyl group
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G , R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX232).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a methyl group
• the structure of G and the substituent R x8 corresponding to the structure of G Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX233).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a fluorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G, Compounds in which R X9 , R X10 and R X11 are any combination described in combination C (hereinafter referred to as compound group SX234).
• X is a nitrogen atom
• L is NH
• R 1 is a methyl group
• R x2 is a chlorine atom
• the structure of G and the substituent R x8 corresponding to the structure of G
• Compounds in which R X9 , R X10 and R X11 are any combination described in combination C hereinafter referred to as compound group SX235).
• R 1 is a methyl group
• R x2 is a methyl group
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 Compounds in which R X18 , R X19 and R X20 are any combination described in combination D (hereinafter referred to as compound group SX236).
• Combination D consists of substituent numbers ZD1 to ZD30.
• Substituent numbers ZD1 to ZD30 represent a combination of R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 in compound (1F).
• the substituent number ZD2 means a combination in which R x12 is a methyl group and R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are hydrogen atoms. .
• R 1 is a methyl group
• R x2 is an ethyl group
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX237).
• R 1 is a methyl group
• R x2 is a fluorine atom
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX238).
• R 1 is a methyl group
• R x2 is a chlorine atom
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX239).
• R 1 is a methyl group
• R x2 is a methoxy group
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX240).
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 is any combination described in combination D (hereinafter referred to as compound group SX241).
• R 1 is a fluorine atom
• R x2 is a methyl group
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are combined
• a compound that is any combination described in D hereinafter referred to as compound group SX242.
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 , R X19 and R X20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX243).
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX244).
• R 1 is a chlorine atom
• R X2 is a methyl group
• R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 , R X19 and R X20 are combined
• a compound that is any combination described in D hereinafter referred to as compound group SX245).
• R 1 is a chlorine atom
• R x2 is a fluorine atom
• R x12 , R x13 , R x14 , R x15 , R x16 , R x17 , R x18 , R x19 and R x20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX246).
• R 1 is a chlorine atom
• R X2 is a chlorine atom
• R X12 , R X13 , R X14 , R X15 , R X16 , R X17 , R X18 , R X19 and R X20 are A compound that is any combination described in combination D (hereinafter referred to as compound group SX247).
• R 1 is a methyl group
• R x2 is a methyl group
• Combination E consists of substituent numbers ZE1 to ZE20.
• Substituent numbers ZE1 to ZE20 represent a combination of R x21 , R x22 , R x23 , R x24 , R x25 , R x26 and R x27 in compound (2F), and hereinafter, [substituent number; R X21 , R X22 , R X23 , R X24 , R X25 , R X26 , R X27 ].
• the substituent number ZE2 means a combination in which R x21 is a methyl group and R x22 , R x23 , R x24 , R x25 , R x26 and R x27 are hydrogen atoms.
• R 1 is a methyl group
• R x2 is an ethyl group
• R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E
• a compound that is a combination of (hereinafter referred to as compound group SX249).
• R 1 is a methyl group
• R x2 is a fluorine atom
• R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of combination E
• a compound that is a combination of hereinafter referred to as compound group SX250).
• R 1 is a methyl group
• R x2 is a chlorine atom
• R x21 , R x22 , R x23 , R x24 , R x25 , R x26 and R x27 are any of those described in combination E
• compound group SX251 compound that is a combination of
• R 1 is a methyl group
• R x2 is a methoxy group
• R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E
• a compound that is a combination of (hereinafter referred to as compound group SX252).
• R 1 is a methyl group
• R x2 is a cyclopropyl group
• R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are according to combination E Any combination of compounds (hereinafter referred to as compound group SX253).
• R 1 is a fluorine atom
• R x2 is a methyl group
• R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E (hereinafter referred to as compound group SX254).
• R 1 is a fluorine atom
• R X2 is a fluorine atom
• R X21 , R X22 , R X23 , R X24 , R X25 , R X26 , and R X27 are any of those described in combination E
• a compound that is a combination of (hereinafter referred to as compound group SX255).
• R 1 is a fluorine atom
• R x2 is a chlorine atom
• R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E
• a compound that is a combination of (hereinafter referred to as compound group SX256).
• R 1 is a chlorine atom
• R x2 is a methyl group
• R x21 , R x22 , R x23 , R x24 , R x25 , R x26 , and R x27 are any of those described in combination E (hereinafter referred to as compound group SX257).
• R 1 is a chlorine atom
• R X2 is a fluorine atom
• R X21 , R X22 , R X23 , R X24 , R X25 , R X26 , and R X27 are any of those described in combination E
• a compound that is a combination of (hereinafter referred to as compound group SX258).
• R 1 is a chlorine atom
• R X2 is a chlorine atom
• R X21 , R X22 , R X23 , R X24 , R X25 , R X26 and R X27 are any of those described in combination E
• a compound that is a combination of (hereinafter referred to as compound group SX259).
• Compound S of the present invention represents compounds described in compound groups SX1 to SX259.
• Formulation example 1 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts of any one of the compounds S of the present invention, and 55 parts of water are mixed and finely pulverized by a wet pulverization method. By doing so, a formulation is obtained.
• Formulation example 2 A formulation is obtained by pulverizing and mixing 50 parts of any one compound S of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica.
• Formulation example 3 5 parts of any one of the compounds S of the present invention, 9 parts of polyoxyethylene styryl phenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide additions: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are mixed. By doing so, a formulation is obtained.
• Formulation example 4 2 parts of any one of the compound S of the present invention, 1 part of silica, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are pulverized and mixed, kneaded with an appropriate amount of water, and granulated. After granulating with, the formulation is obtained by drying.
• Formulation example 5 10 parts of any one of the compounds S of the present invention are mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, to which 6.3 parts of GERONOL® TE250, Ethylan® NS-500LQ2 are added. Add .7 parts and 54 parts solvent naphtha and mix to obtain a formulation.
• Formulation example 6 0.1 part of any one of the compound S of the present invention and 39.9 parts of kerosene are mixed and dissolved, placed in an aerosol container, and liquefied petroleum gas (propane, butane and isobutane mixture; saturated vapor pressure: 0.47 MPa (25 C))) to obtain a formulation by filling 60 parts.
• liquefied petroleum gas propane, butane and isobutane mixture; saturated vapor pressure: 0.47 MPa (25 C)
• Formulation example 7 0.2 parts of any one of the compounds S of the present invention, 50 parts of pyrethrum extract lees powder, 30 parts of tab powder and 19.8 parts of wood powder are mixed, kneaded by adding an appropriate amount of water, and extruded into a plate shape.
• the formulation is obtained by sheeting and coiling with a punch.
• Test Examples 1 to 8 is a test section performed under the same conditions as described in each Test Example except that DMSO is dispensed instead of the DMSO diluted solution containing the compound of the present invention. represents Further, "no treatment" in Test Examples 9 to 19 means that the water-diluted formulation containing the compound of the present invention was not sprayed.
• the untreated section in Test Examples 20 and 23 means a section in which the same operation as the treated section is performed except that no test compound is used.
• Test Example 1 Control test against wheat leaf blight fungus (Septoria tritici) Compounds of the present invention 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 2-1, 3-1, 3 -2, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 5-1, 6-1, 1-7, 1-8, 1-9, 2-2 , 2-3, 3-3, 3-4, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4 -16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28 , 4-29, 4-30, 5-2, 5-3, 5-4, 5-5, or 6-2 is diluted with DMSO to contain 150 ppm, and 1 ⁇ L is dispensed to a titer plate (96 wells) After that, 150 ⁇ L of YBG medium previously inoculated with spores of wheat leaf
• the absorbance at 550 nm of each well of the titer plate was measured, and the value was defined as the growth rate of the wheat leaf blight fungus.
• the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
• Test Example 2 Control test against Phytophthora capsici Compounds of the present invention 1-2, 1-7, 1-8, 1-9, 2-3, 4-7, 4-9, 4-13, Dilute 4-14, 4-15, 4-16, 4-18, 4-19, or 4-20 with DMSO to contain 150 ppm, dispense 1 ⁇ L into a titer plate (96 wells), and then add cucumber in advance. 150 ⁇ L of a potato decoction liquid medium (PDB medium) inoculated with spores of Gray-like Phytophthora was dispensed. This plate was cultured at 27° C.
• PDB medium potato decoction liquid medium
• the absorbance at 550 nm of each well of the titer plate was measured to determine the growth rate of Cucurbitaceae Botrytis.
• the growth rate in the section treated with the compound of the present invention was 50% or less of the growth rate in the untreated section.
• Test Example 3 Control test against seedling blight (Pythium ultimum) Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-3, 1 -5, 1-6, 1-7, 1-8, 1-9, 2-3, 3-1, 3-2, 3-4, 4-7, 4-8, 4-9, 4-12 , 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-23, 4-24, 4-25, 4-26, 4 -27, 4-28, 4-29, 5-1, or 5-2 diluted with DMSO to contain 150 ppm, dispensed 1 ⁇ L into a titer plate (96 wells), and then spores of seedling blight in advance 150 ⁇ L of the Czapek medium inoculated with .
• the absorbance at 550 nm of each well of the titer plate was measured, and the value was defined as the growth rate of the damping-off fungus.
• the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
• Test Example 4 Control test against corn smut (Ustilago maydis) Compounds of the present invention 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-5, 1-7, 1- 8, 1-9, 2-3, 4-1, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-19, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-4, or 6 -2 was diluted with DMSO to contain 150 ppm, 1 ⁇ L was dispensed into a titer plate (96 wells), and then 150 ⁇ L of potato decoction liquid medium (PDB medium) previously inoculated with corn smut spores was dispensed.
• PDB medium potato decoction liquid medium
• This plate was cultured at 18° C. for 4 days to grow the corn smut fungus, and then the absorbance at 550 nm of each well of the titer plate was measured to determine the growth rate of the corn smut fungus.
• the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
• Test Example 5 Control test against Rhynchosporium secalis Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1- 3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4- 17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 was diluted with DMSO to contain 150 ppm, and 1 ⁇ L was dispensed into a titer plate (96 wells).
• Test Example 6 Control test against cucumber gray mold (Botrytis cinerea) Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1 -3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4 , 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4 -17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29 , 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 is diluted with DMSO to contain 150 ppm, and 1 ⁇ L is dispensed to a titer plate (96 well) After that, 150 ⁇ L of a complete medium previously inoculated with spores of Botrytis botrytis was
• the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the cucumber botrytis.
• the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
• Test Example 7 Control test against peach scab (Cladosporium carpophilum) Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1- 3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4- 17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 was diluted with DMSO to contain 150 ppm, and 1 ⁇ L was dispensed into a titer plate (96 wells).
• Test Example 8 Control test against rice sesame leaf blight fungus (Cochliobolus miyabeanus) Compounds of the present invention 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3- 4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-24, 4-25, 4-26, 4-27, 4-29, 4-30, 5- 1, 5-2, 5-3, 5-4, or 5-5 is diluted with DMSO to contain 150 ppm, and 1 ⁇ L is dispensed into a titer plate (96 wells), and then spores of rice sesame leaf blight fungus are added in advance.
• DMSO DMSO
• the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the rice and sesame leaf blight fungus.
• the growth rates in the plots treated with the compounds of the present invention were all 50% or less of the growth rate in the untreated plots.
• Test Example 9 Prevention test against soybean rust (Phakopsora pachyrhizi) A leaf disc having a diameter of 1 cm was cut out from a true leaf of soybean (variety: Kurosengoku). After 1 mL of agar medium (agar concentration: 1.2%) was dispensed into each well of a 24-well microplate, one leaf disk was placed on each well of the agar medium. To a mixture of 0.5 ⁇ L of Sorpol® 1200KX, 4.5 ⁇ L of DMSO and 5 ⁇ L of xylene, 20 ⁇ L of DMSO solution containing 10000 ppm of the test compound was added and mixed.
• the obtained mixture was diluted with ion-exchanged water to prepare a mixture containing the test compound at a predetermined concentration. 10 ⁇ L of the resulting mixture was spread on each leaf disc.
• an aqueous spore suspension (1.0 ⁇ 10 5 /mL) of Phakopsora pachyrhizi having an amino acid substitution of F129L in the mitochondrial cytochrome b protein was spray-inoculated onto the leaf discs. After inoculation, the plants were placed in an artificial climate chamber (6 hours light, 18 hours light off, temperature 23°C, humidity 60%). After one day, the leaf disc was air-dried until no water droplets were left on the surface, and placed again in the climate chamber for 12 days.
• the lesion area of soybean rust was investigated.
• the predetermined concentration was set to 50 ppm
• Leaf disc lesion area treated with any one of 4-27, 4-28, 4-29, 5-1, 5-2, 5-3, 5-4, 5-5, and 6-2 was 30% or less of the lesion area of untreated leaf discs.
• the resulting mixture was foliarly sprayed so as to sufficiently adhere to the foliage of the barley.
• the barley was air-dried, and one day later, an aqueous suspension of spores of barley net spot fungus was inoculated by spraying.
• the barley was placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 3 days, then cultivated in the greenhouse for 7 days, and then the lesion area was examined.
• the lesion area in barley treated with each compound of the present invention was 30% or less of the lesion area in untreated barley.
• Test Example 11 Prevention test against wheat rust (Puccinia recondita) A plastic pot was filled with soil, wheat (cultivar: Shirogane) was sown therein, and cultivated in a greenhouse for 9 days.
• the lesion area in the wheat treated with each compound of the present invention was 30% or less of the lesion area in the untreated wheat.
• Test Example 12 Control Test against Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, and wheat (variety: Apogee) was sown therein and cultivated in a greenhouse for 10 days.
• the wheat After spraying, the wheat was air-dried, and four days later, an aqueous suspension containing spores of the wheat leaf blight fungus was inoculated by spraying. After inoculation, the wheat was placed under high humidity at 18°C for 3 days, then cultivated under lighting for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the wheat treated with each compound of the present invention was 30% or less of the lesion area in the untreated wheat.
• Test Example 13 Control test against wheat leaf blight (Septoria tritici) Plastic pots were filled with soil, wheat (cultivar: Apogee) was sown there, cultivated in a greenhouse for 10 days, and wheat leaf blight spores were suspended in water. The liquid was spray inoculated. After inoculation, the wheat was placed under high humidity at 18° C. for 3 days, and then compounds 1-2, 2-1, 3-1, 4-2, and 4- of the present invention were formulated according to the method described in Formulation Example 1.
• Test Example 14 Prevention test against tomato late blight (Phytophthora infestans) Plastic pots were filled with soil, tomatoes (variety: patio) were seeded therein, and cultivated in a greenhouse for 20 days.
• the tomatoes After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying an aqueous suspension containing spores of Tomato Phytophthora. After inoculation, the tomatoes were placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 1 day, then cultivated in the greenhouse for 4 days, and then the lesion area was examined. As a result, the lesion area on tomatoes treated with the compounds of the present invention was 30% or less of the lesion area on untreated tomatoes.
• Test Example 15 Prevention test against soybean rust (Phakopsora pachyrhizi) Plastic pots were filled with soil, soybeans (cultivar: Kurosengoku) were sown therein, and grown in a greenhouse for 10 to 14 days.
• the soybeans After spraying, the soybeans were air-dried, and 2 to 5 days later, an aqueous suspension of soybean rust spores was inoculated by spraying. After inoculation, the soybeans were placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 1 to 2 days, then cultivated in the greenhouse for 12 days, and then the lesion area was examined. As a result, the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
• Test Example 16 Control test against soybean rust (Phakopsora pachyrhizi) Plastic pots were filled with soil, soybeans (cultivar: Kurosengoku) were sown there, grown in a greenhouse for 10 days, and water suspensions containing spores of soybean rust fungi were obtained. The suspension was spray inoculated. After inoculation, the soybeans were placed in a greenhouse at 23°C during the day and 20°C at night under high humidity for 1 day, and then cultivated in the greenhouse for 2 days.
• Test Example 17 Prevention test against soybean spot disease (Cercospora sojina) A plastic pot was filled with soil, soybeans (cultivar: Tachinagaha) were sown therein and grown in a greenhouse for 13 days. Compounds 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 4-4, 4-5 and 6 of the present invention formulated according to the method described in Formulation Example 1 -1, 1-7, 1-8, 1-9, 3-1, 3-2, 4-14, 4-16, 4-17, 4-19, 4-20, 4-21, 4-22 , 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-4, 5-5, 6-2, or 2-3 with a concentration of 200 ppm The resulting mixture was foliarly sprayed so that it adhered sufficiently to the leaves of the soybean.
• the soybeans After spraying, the soybeans were air-dried, and one day later, they were inoculated by spraying an aqueous suspension of spores of the soybean leaf spot fungus. After inoculation, the soybeans were placed in a greenhouse at 23° C. during the day and 20° C. at night under high humidity for 3 days, then cultivated in the greenhouse for 16 days, and then the lesion area was examined. As a result, the lesion area in the soybeans treated with each compound of the present invention was 30% or less of the lesion area in the untreated soybeans.
• Test Example 18 Prevention test against tomato ring spot (Alternaria solani) Plastic pots were filled with soil, tomatoes (variety: Patio) were sown therein, and grown in a greenhouse for 20 days.
• the tomatoes After spraying, the tomatoes were air-dried, and one day later, they were inoculated by spraying an aqueous suspension of spores of tomato ring-blight fungus. After the inoculation, the tomato was placed at 18° C. and high humidity for 6 days, and then the lesion area was examined. As a result, the lesion area on tomatoes treated with the compounds of the present invention was 30% or less of the lesion area on untreated tomatoes.
• Test Example 19 Control test against bean sclerotinia (Sclerotinia sclerotiorum) Plastic pots were filled with soil, and bean beans (variety: long quail bean) were sown and grown in a greenhouse for 8 days.
• the green beans After spraying, the green beans were air-dried, and a PDA medium containing mycelia of Sclerotinia vulgaris was placed on the leaves of the green beans. After inoculation, all green beans were placed under high humidity only at night, and the area of lesions was examined 4 days after inoculation. As a result, the lesion area in the green beans treated with each compound of the present invention was 30% or less of the lesion area in the untreated green beans.
• Test method 20 Test against Aphis gossypii
• a test compound is prepared according to the method described in Formulation Example 1, water containing 0.03% by volume of a spreading agent is added, and a diluted solution containing a predetermined concentration of the test compound is added. to prepare.
• a cucumber (Cucumis sativus) seedling (second true leaf development stage) planted in a container is inoculated with about 30 Aphis gossypii (all stages). After 1 day, the seedlings are sprayed with the diluted solution at a rate of 10 mL/seedling. After another 5 days, the number of surviving insects is investigated, and the control value is determined by the following formula.
• Control value (%) ⁇ 1-(Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
• Cb Number of test insects in untreated area
• Cai Number of surviving insects in untreated area during survey
• Tb Number of test insects in treated area Tai: Surviving number of insects in treated area during survey
• Test example 20 As a result of testing according to Test Method 20 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, all of the compounds of the present invention exhibited a control value of 90% or more.
• Compounds of the present invention 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 6-1, 1-1, 1-6, 1-7, 1-9, 4- 1, 4-7, 4-9, 4-10, 4-11, 4-12, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-23, 4-24, 4-25, 4-29, 5-1, 6-2
• Test example 21 As a result of testing according to Test Method 21 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, all of the compounds of the present invention showed a mortality rate of 90% or more.
• Compounds of the present invention 1-2, 2-1, 3-1, 3-2, 6-1, 1-6, 1-7, 1-9, 2-2, 3-3, 4-7, 4- 14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-29, 6-2
• Test example 22 As a result of testing according to Test Method 22 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, all of the compounds of the present invention showed a mortality rate of 80% or more.
• Compounds of the present invention 3-1, 3-2, 4-2, 6-1, 4-7, 4-15, 4-18, 4-13, 1-7, 1-8, 1-9, 4- 14, 4-17, 4-29, 4-22, 4-23, 4-24, 4-25
• Test method 23 Test against two-spotted spider mite
• the test compound is prepared according to the method described in Formulation Example 1, and water containing 0.03% by volume of Syndyne (registered trademark) is added to dilute the test compound to a predetermined concentration. Prepare the liquid. Approximately 40 two-spotted spider mite female adults are released on kidney bean (Phaseolus vulgaris) seedlings (first true leaf development stage) planted in a container. After one day, the seedlings are sprayed with the diluted solution at a rate of 10 mL/seedling. After 13 days, the number of surviving insects is investigated, and the control value is calculated according to the following formula.
• Control value (%) ⁇ 1-(Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
• Cb Number of test insects in untreated area
• Cai Number of surviving insects in untreated area during survey
• Tb Number of test insects in treated area Tai: Surviving number of insects in treated area during survey
• Test example 23 As a result of testing according to Test Method 23 using the following compounds of the present invention as test compounds at a predetermined concentration of 500 ppm, all of the compounds of the present invention exhibited a control value of 90% or more.
• Compounds of the present invention 1-2, 2-1, 3-1, 3-2, 4-2, 6-1, 1-3, 1-6, 2-2, 2-3, 3-3, 4- 7, 4-9, 4-10, 4-11, 4-15, 4-16, 4-17, 4-18, 4-19, 4-21, 4-22, 4-24, 4-25, 4-27, 4-29, 5-5
• the compound of the present invention has a controlling effect on pests and can be used for controlling pests.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Zoology (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Environmental Sciences (AREA)
• Wood Science & Technology (AREA)
• Animal Behavior & Ethology (AREA)
• Pharmacology & Pharmacy (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• Epidemiology (AREA)
• Medicinal Chemistry (AREA)
• Agronomy & Crop Science (AREA)
• Dentistry (AREA)
• General Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Insects & Arthropods (AREA)
• Mycology (AREA)
• Microbiology (AREA)
• Emergency Medicine (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Plural Heterocyclic Compounds (AREA)
• Pyridine Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

Priority Applications (5)

Applications Claiming Priority (4)

Publications (1)

Family

ID=83047575

Family Applications (1)

Country Status (7)

Cited By (2)

Citations (11)

Family Cites Families (5)

• 2022
  • 2022-02-25 WO PCT/JP2022/008031 patent/WO2022181793A1/ja not_active Ceased
  • 2022-02-25 UY UY0001039647A patent/UY39647A/es unknown
  • 2022-02-25 EP EP22759827.3A patent/EP4299557A4/en active Pending
  • 2022-02-25 BR BR112023017023A patent/BR112023017023A2/pt unknown
  • 2022-02-25 US US18/546,735 patent/US20240190805A1/en active Pending
  • 2022-02-25 JP JP2023502557A patent/JP7787870B2/ja active Active
  • 2022-02-25 PY PY202202212961A patent/PY2212961A/es unknown

Patent Citations (11)

Non-Patent Citations (2)

Also Published As

Similar Documents