WO2013058256A1 - Composé hétérocyclique azoté, et agent bactéricide à visée agricole et horticole - Google Patents

Composé hétérocyclique azoté, et agent bactéricide à visée agricole et horticole Download PDF

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WO2013058256A1
WO2013058256A1 PCT/JP2012/076767 JP2012076767W WO2013058256A1 WO 2013058256 A1 WO2013058256 A1 WO 2013058256A1 JP 2012076767 W JP2012076767 W JP 2012076767W WO 2013058256 A1 WO2013058256 A1 WO 2013058256A1
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勇人 齊木
頼人 ▲桑▼原
準 稲垣
元亮 佐藤
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日本曹達株式会社
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    • 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
    • A01N43/42—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 condensed with carbocyclic 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • 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
    • A01N43/80—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 1,2
    • 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
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a nitrogen-containing heterocyclic compound or a salt thereof or an N-oxide compound. More specifically, the present invention relates to an agricultural and horticultural fungicide that can be used safely and safely, and a nitrogen-containing heterocyclic compound or a salt or N-oxide compound useful as an active ingredient of the agricultural and horticultural fungicide.
  • This application claims priority based on Japanese Patent Application No. 2011-228373 for which it applied to Japan on October 17, 2011, and uses the content here.
  • Patent Documents 1 to 3 disclose a quinoline derivative having a chemical structure similar to that of the compound of the present invention and an agricultural and horticultural fungicide containing it as an active ingredient.
  • An object of the present invention is to provide an agricultural and horticultural fungicide that can be used safely and reliably, and a nitrogen-containing heterocyclic compound or a salt or N-oxide compound useful as an active ingredient of the agricultural and horticultural fungicide. To do.
  • Cy represents an unsubstituted or substituted oxiranyl group or an unsubstituted or substituted 5- to 6-membered heterocyclic group.
  • B represents a nitrogen atom or a carbon atom.
  • D represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
  • X 1 is each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted A 5- to 6-membered heterocyclic group having, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted group Having a carboxyl group, an unsubstituted or substituted carbamoyl group, an unsubstituted or substituted hydroxyl group, an unsubstituted or substituted group An amino group, an un
  • m represents the number of X 1 and is an integer from 0 to 6.
  • E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
  • X 2 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted A 5- to 6-membered heterocyclic group having, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted group Having a carb
  • n represents the number of X 2 and is an integer from 0 to 4.
  • X represents an oxygen atom, a sulfur atom, a group represented by —C ( ⁇ O) — group, or a group represented by —CHOH— group.
  • Cy, X ⁇ 1 >, m, X ⁇ 2 >, n, B, and X show the same meaning as each in said formula (1).
  • a 1 , A 2 , A 3 , and A 4 each independently represent a carbon atom or a nitrogen atom.
  • n1 represents the number of X 2 and is an integer from 0 to 3.
  • a 5 , A 6 , and A 7 each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom. However, oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other.
  • the nitrogen-containing heterocyclic compound of the present invention is a novel compound useful as an active ingredient of agricultural and horticultural fungicides.
  • the agricultural and horticultural fungicide of the present invention is a safe drug that has a reliable and excellent control effect, does not cause phytotoxicity on plants, and has little toxicity to human and livestock and environmental impact.
  • the present inventors have found that the nitrogen-containing heterocyclic compounds of the nitrogen-containing heterocyclic compounds represented by the formulas (1) to (4) have a certain effect and can be used safely as active ingredients of agricultural and horticultural fungicides.
  • the present invention has been completed through further studies based on the findings.
  • Nitrogen-containing heterocyclic compound [compound represented by formula (1)]
  • the nitrogen-containing heterocyclic compound according to the present invention is a compound represented by the formula (1) (hereinafter sometimes referred to as “compound (1)”), a salt thereof or an N-oxide compound.
  • the nitrogen-containing heterocyclic compound according to the present invention includes hydrates, various solvates and crystal polymorphs. Furthermore, the nitrogen-containing heterocyclic compound according to the present invention includes stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures thereof.
  • unsubstituted means only the group that is the mother nucleus.
  • the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure as the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus.
  • the number of substituents may be one, or two or more. Two or more substituents may be the same or different. Terms such as “C1-6” indicate that the group serving as the mother nucleus has 1 to 6 carbon atoms. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
  • substituted is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
  • groups that can be “substituents” include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n-propyl, i-propyl, n-butyl, and s-butyl.
  • a C1-6 alkyl group such as a group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; a C3-6 cycloalkyl group such as a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group C2-6 alkenyl groups such as nyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group
  • C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; vinyloxy group, allyloxy group, propenyl C2-6 alkenyloxy groups such as oxy and butenyloxy groups; C2-6 alkynyloxy groups such as ethynyloxy and propargyloxy groups; C6-10 aryl groups such as phenyl and naphthyl groups; phenoxy groups and 1-naphthoxy groups C7-10 aryloxy group such as benzyl group, phenethyl group, etc .; C7-11 aralkyloxy group such as benzyloxy group, phenethyloxy group; formyl group, acetyl group, propionyl group, benzoyl group, Such as cyclohexylcarbonyl group 1-7
  • oxo group O
  • chloromethyl group chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group, etc.
  • C1-6 haloalkyl group C2-6 haloalkenyl group such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl Groups, C2-6 haloalkynyl groups such as 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group and 2,3-dichlorobutoxy group; 2-chloropropenyloxy group C2-6 haloalkenyloxy groups such as 3-bromobutenyloxy group; 4-chlorophenyl group, 4-fluorophenyl group, 2, -C6-10 haloaryl group such as dichlorophenyl group; C6-10 haloaryloxy group such as 4-fluorophenyloxy group, 4-chloro-1-naphthoxy group; chloroacety
  • C1-7 acylamino group C1-6 alkoxycarbonylamino group such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; carbamoyl group; Substituted carbamoyl groups such as dimethylcarbamoyl group, phenylcarbamoyl group, N-phenyl-N-methylcarbamoyl group; imino C1-6 such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group Alkyl groups; hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group; methoxyiminomethyl group, (1-methoxyimino) ethyl group, etc.
  • C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C2-6 alkenylsulfinyl groups such as allylsulfinyl group; C2-6 alkynylsulfinyl groups such as propargylsulfinyl group; phenylsulfinyl group, etc.
  • 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, pyrazinyl Group, 6-membered heteroaryl group such as pyrimidinyl group, pyridazinyl group, triazinyl group; saturated heterocyclic group such as pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group; trimethylsilyl group, triethylsilyl group, t-butyl A tri-C1-6 alkylsilyl group such as a dimethylsilyl group; a triphenylsilyl group; and the like.
  • substituteduents may have another “substituent” therein.
  • a butyl group as a substituent and an ethoxy group as another substituent, that is, an ethoxybutyl group may be used.
  • Cy represents an unsubstituted or substituted oxiranyl group or an unsubstituted or substituted 5- to 6-membered heterocyclic group.
  • the “5- to 6-membered heterocyclic group” includes 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring.
  • Cy includes an unsubstituted or substituted oxiranyl group, an unsubstituted or substituted 5-membered heteroaryl group, an unsubstituted or substituted 6-membered heteroaryl group, an unsubstituted or substituted group.
  • a partially unsaturated 5-membered heterocyclic group, an unsubstituted or substituted partially unsaturated 6-membered heterocycle, an unsubstituted or substituted saturated 5-membered heterocyclic group, or unsubstituted or A saturated 6-membered heterocyclic group having a substituent is preferable.
  • 5-membered heteroaryl groups include: pyrrolyl groups such as pyrrol-1-yl, pyrrol-2-yl, and pyrrol-3-yl; furyl groups such as furan-2-yl and furan-3-yl ; Thienyl groups such as thiophen-2-yl group and thiophen-3-yl group; imidazolyl groups such as imidazol-1-yl group, imidazol-2-yl group, imidazol-4-yl group and imidazol-5-yl group ; Pyrazolyl groups such as pyrazol-1-yl group, pyrazol-3-yl group, pyrazol-4-yl group, pyrazol-5-yl group; oxazol-2-yl group, oxazol-4-yl group, oxazole-5 -Oxazolyl groups such as yl groups; isoxazol-3-yl groups, isoxazol-4-yl groups, iso
  • the 6-membered heteroaryl group includes pyridyl groups such as pyridin-2-yl group, pyridin-3-yl group and pyridin-4-yl group; pyrazinyl groups such as pyrazin-2-yl group and pyrazin-3-yl group A pyrimidinyl group such as a pyrimidin-2-yl group, a pyrimidin-4-yl group and a pyrimidin-5-yl group; a pyridazinyl group such as a pyridazin-3-yl group and a pyridazin-4-yl group; a triazinyl group; It is done.
  • Partially unsaturated 5-membered heterocyclic groups include pyrrolinyl groups such as 2-pyrrolin-3-yl group; 2-imidazolin-1-yl group, 2-imidazolin-2-yl group, 2-imidazolin-4-yl Groups, imidazolinyl groups (dihydroimidazolinyl groups) such as 2-imidazolin-5-yl group; 3-pyrazolin-1-yl group, 3-pyrazolin-2-yl group, 3-pyrazolin-3-yl group, 3 -Pyrazolinyl groups such as pyrazolin-4-yl group and 3-pyrazolin-5-yl group; oxazolinyl groups such as 2-oxazolin-2-yl group, 2-oxazolin-4-yl and 2-oxazolin-5-yl; Such as 2-isoxazolin-3-yl group, 2-isoxazolin-4-yl group, 2-isoxazolin
  • the partially unsaturated 6-membered heterocyclic group includes pyranyl group such as 2H-pyran-3-yl group; thiopyranyl group such as 2H-thiopyran-3-yl group; 2H-pyridin-1-yl group, 4H-pyridine -1-yl group; and the like.
  • saturated 5-membered heterocyclic groups include pyrrolidinyl groups such as pyrrolidin-1-yl group, pyrrolidin-2-yl group, and pyrrolidin-3-yl group; tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group and the like.
  • saturated 6-membered heterocyclic group examples include piperidinyl groups such as piperidin-1-yl group, piperidin-2-yl group, piperidin-3-yl group, piperidin-4-yl group; piperazin-1-yl group, piperazine And piperazinyl groups such as -2-yl group; morpholinyl groups such as morpholin-2-yl group, morpholin-3-yl group and morpholin-4-yl group.
  • Cy includes pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, oxadiazolyl, pyridyl, isoxazolinyl, pyrrolidinyl, or dioxolanyl. More preferably.
  • substituent on Cy examples include the same as those exemplified as the “substituent” above.
  • Examples of the 5- to 6-membered heterocyclic group having an oxo group ( ⁇ O) include 2-oxo-pyrrolidin-1-yl, 2-oxo-piperidin-1-yl, 2-oxo-2H-pyridin-1-yl, etc. Is mentioned. Of these, 2-oxo-pyrrolidin-1-yl is preferred.
  • Cy is a 5- to 6-membered heterocyclic group
  • a substituent on Cy may be present adjacent to each other, and together, an unsubstituted or substituted 5- to 8-membered ring may be formed.
  • Examples of 5- to 8-membered rings that can be formed together include aromatic hydrocarbon rings such as benzene rings; C5-8 cycloalkene rings such as cyclopentene rings, cyclopentadiene rings, cyclohexene rings, cycloheptene rings, and cyclooctene rings; Etc.
  • [B, D] B represents a carbon atom or a nitrogen atom. That is, a pyridine ring formed by condensation of “D” or a pyrazine ring formed by condensation of “D” is formed. D is a part of a ring constituting a pyridine ring or a pyrazine ring, and represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocycle.
  • 5- to 7-membered hydrocarbon rings include aromatic hydrocarbon rings such as benzene rings; cycloalkene rings such as cyclopentene rings, cyclohexene rings, and cycloheptene rings; cycloalkane rings such as cyclopentane rings, cyclohexane rings, and cycloheptane rings. Is mentioned.
  • the 5- to 7-membered heterocycle includes a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a thiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, and a pyridazine ring.
  • Azepine ring diazepine ring; dihydro-2H-pyran ring, dihydro-2H-thiopyran ring, tetrahydropyridine ring; hexamethyleneimine ring, 2-ketohexamethyleneimine ring, homopiperazine ring and the like.
  • D an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable.
  • the compound (1) is preferably a compound having a quinoline ring or a quinoxaline ring.
  • X 1 is D and / or a substituent of a pyridine ring or a pyrazine ring, each independently an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 An alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, an unsubstituted Or a substituted C6-10 aryl group, an unsubstituted or substituted 5- to 6-membered heterocyclic group, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted group ( 1-imino) C1-8 alkyl group, unsubstituted or substituted carboxyl group, unsubstituted or substituted carbamoyl group, un
  • the “C1-8 alkyl group” in X 1 is a saturated hydrocarbon group composed of 1 to 8 carbon atoms.
  • the C1-8 alkyl group may be linear or branched.
  • Examples of the C1-8 alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, i-propyl group, i -Butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.
  • C1-6 alkyl groups are preferred.
  • Examples of the “substituted C1-8 alkyl group” include cycloalkylalkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, preferably C3-6 cycloalkylC1.
  • cycloalkenylalkyl group such as cyclopentenylmethyl group, 3-cyclopentenylmethyl group, 3-cyclohexenylmethyl group, 2- (3-cyclohexenyl) ethyl group, preferably C4-6 cycloalkenylC1 ⁇ 6 alkyl groups; fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl Group 2,2,2-tri Loroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group, perfluorohexyl Group, perchlorohexyl group,
  • Haloalkyl groups preferably C1-6 haloalkyl groups; arylalkyl groups (aralkyl groups) such as benzyl group, phenethyl group, 3-phenylpropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, preferably C6-10 An aryl C1-6 alkyl group;
  • 2-hydroxyiminoalkyl groups such as 2-hydroxyiminoethyl group, 2-hydroxyimino-1-methylethyl group, 2-hydroxy-1,1-dimethylethyl group, 2-hydroxyiminopropyl group, preferably 2-hydroxy An imino C2-6 alkyl group; an acylalkyl group such as an acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, 1-acetyl-1-methylethyl group, 2-acetyl-1,1-dimethylethyl group; Preferably formyl C1-6 alkyl group; carboxyalkyl such as carboxymethyl group, 2-carboxyethyl group, 3-carboxypropyl group, 1-carboxy-1-methylethyl group, 2-carboxy-1,1-dimethylethyl group Group, preferably a carboxy C1-6 alkyl group; methoxycarbo An alkoxycarbonylalkyl group such
  • the “C2-8 alkenyl group” in X 1 is an unsaturated hydrocarbon group composed of 2 to 8 carbon atoms having at least one carbon-carbon double bond.
  • the C2-8 alkenyl group may be linear or branched.
  • C2-8 alkenyl groups include vinyl, 1-propenyl, isopropenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, 1-heptenyl group, 6-heptenyl group, 1-octenyl group, 7- Examples include octenyl group, 1-methyl-allyl group, 2-methyl-allyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group and the like. Of these, C2-6
  • Examples of the “substituted C2-8 alkenyl group” include 3-chloro-2-propenyl group, 4-chloro-2-butenyl group, 4,4-dichloro-3-butenyl group, 4,4-difluoro-3 -Butenyl group, 3,3-dichloro-2-propenyl group, 2,3-dichloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,4,6-trichloro-2-hexenyl group, etc.
  • Haloalkenyl groups preferably C2-6 haloalkenyl groups; hydroxyalkenyl such as 3-hydroxy-1-propenyl, 4-hydroxy-1-butenyl, 1-hydroxyallyl, 1-hydroxy-2-methylallyl Group, preferably a hydroxy C2-6 alkenyl group; and the like.
  • the “C2-8 alkynyl group” in X 1 is an unsaturated hydrocarbon group composed of 2 to 8 carbon atoms having at least one carbon-carbon triple bond.
  • the C2-8 alkynyl group may be linear or branched.
  • C2-8 alkynyl groups include ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4 -Pentynyl, 1-hexynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 2-methyl-3-pentynyl, 1,1-dimethyl And a -2-butynyl group.
  • C2-6 alkynyl groups are preferred.
  • Examples of the “substituted C2-8 alkynyl group” include 3-chloro-1-propynyl group, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 3-bromo-1-hexynyl group, 4,4,6,6-tetrafluoro-1-dodecynyl group, 5,5-dichloro-2-methyl-3-pentynyl group, 4 A haloalkynyl group such as a -chloro-1,1-dimethyl-2-butynyl group, preferably a C2-6 haloalkynyl group.
  • the “C 3-8 cycloalkyl group” in X 1 is an alkyl group composed of 3 to 8 carbon atoms having a cyclic moiety.
  • Examples of the C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Of these, C3-6 cycloalkyl groups are preferred.
  • Examples of the “substituted C3-8 cycloalkyl group” include alkyl substitution such as 2,3,3-trimethylcyclobutyl group, 4,4,6,6-tetramethylcyclohexyl group, 1,3-dibutylcyclohexyl group, etc. Examples thereof include a cycloalkyl group, preferably a C3-6 cycloalkyl group in which 1 to 3 C1-6 alkyl groups are substituted.
  • the “C4-8 cycloalkenyl group” in X 1 is an alkenyl group composed of 4-8 carbon atoms having a cyclic moiety.
  • Examples of the C4-8 cycloalkenyl group include 1-cyclobutenyl group, 1-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 3-cyclohexenyl group, 3-cycloheptenyl group, 4-cyclooctenyl group and the like. It is done.
  • Examples of the “substituted C4-8 cycloalkenyl group” include alkyl-substituted cycloalkenyl groups such as 2-methyl-3-cyclohexenyl group and 3,4-dimethyl-3-cyclohexenyl group, preferably C1-6 alkyl And C4-6 cycloalkenyl groups substituted with 1 to 3 groups.
  • the “C6-10 aryl group” in X 1 is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • the polycyclic aryl group as long as at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
  • the C6-10 aryl group include phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like. Of these, a phenyl group is preferred.
  • substituted C6-10 aryl group examples include 2-chlorophenyl group, 3,5-dichlorophenyl group, 4-fluorophenyl group, 3,5-difluorophenyl group, 4-trifluoromethylphenyl group, 2- Alkyl-substituted aryl group, halogeno-substituted aryl group, alkoxy-substituted aryl group such as methoxy-1-naphthyl group, preferably C1-6 alkyl-substituted C6-10 aryl group, halogeno-substituted C6-10 aryl group, C1-6 alkoxy-substituted An aryl group is mentioned.
  • Examples of the “5- to 6-membered heterocyclic group” in X 1 include the same as those exemplified for Cy.
  • the “C1-8 acyl group” in X 1 is a carbonyl group having a hydrogen atom, a C1-7 alkyl group, a C2-7 alkenyl group, a C2-7 alkynyl group, a C6-7 aryl group, or a 5-7 membered heterocyclic ring. A group to which a group is bonded.
  • C1-8 acyl group includes formyl group; acetyl group, propionyl group, n-propylcarbonyl group, n-butylcarbonyl group, pentanoyl group, valeryl group, octanoyl group, i-propylcarbonyl group, i-butylcarbonyl group, An alkylcarbonyl group such as a pivaloyl group and an isovaleryl group, preferably a C1-6 alkylcarbonyl group; an alkenylcarbonyl group such as an acryloyl group and a methacryloyl group, preferably a C2-6 alkenylcarbonyl group; an alkynylcarbonyl group such as a propioroyl group, preferably C2-6 alkynylcarbonyl groups; arylcarbonyl groups such as benzoyl groups; heterocyclic carbonyl groups such as 2-pyridylcarbonyl groups and thienyl
  • Examples of the “substituted C1-8 acyl group” include a monofluoroacetyl group, a monochloroacetyl group, a monobromoacetyl group, a difluoroacetyl group, a dichloroacetyl group, a dibromoacetyl group, a trifluoroacetyl group, a trichloroacetyl group, a trichloroacetyl group, Haloacyl groups such as bromoacetyl group, 3,3,3-trifluoropropionyl group, 3,3,3-trichloropropionyl group, 2,2,3,3,3-pentafluoropropionyl group, preferably C1-7 haloacyl Groups and the like.
  • the “(1-imino) C1-8 alkyl group” in X 1 is an iminomethyl group or a group in which a C1-7 alkyl group is bonded to an iminomethyl group.
  • the (1-imino) C1-8 alkyl group includes an iminomethyl group, a (1-imino) ethyl group, a (1-imino) propyl group, a (1-imino) butyl group, a (1-imino) pentyl group, (1 -Imino) hexyl group, (1-imino) heptyl group and the like. Of these, (1-imino) C1-6 alkyl groups are preferred.
  • Examples of the “(1-imino) alkyl group having a substituent” include (hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group, (1-hydroxyimino) butyl group, etc.) 1-hydroxyimino) C1-8 alkyl group; preferably (1-hydroxyimino) C1-6 alkyl group; methoxyiminomethyl group, (1-ethoxyimino) methyl group, (1-methoxyimino) ethyl group, (1 A (1-alkoxyimino) C1-8 alkyl group such as a -t-butoxyimino) ethyl group or a (1-ethoxyimino) ethyl group, preferably a (1- (C1-6alkoxy) imino) C1-6 alkyl group; Etc.
  • the “carboxyl group having a substituent” in X 1 is a carbonyl group having a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C6-10 aryl group, a C6-10 aryl C1-6 alkyl. Or a group to which a 5- or 6-membered heterocyclic group is bonded.
  • Examples of the “substituted carboxyl group” include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, n
  • An alkoxycarbonyl group such as a pentyloxycarbonyl group or an n-hexyloxycarbonyl group, preferably a C1-6 alkoxycarbonyl group; an alkenyloxycarbonyl group such as a vinyloxycarbonyl group or an allyloxycarbonyl group, preferably a C2-6 alkenyloxy
  • An alkynyloxycarbonyl group such as an ethynyloxycarbonyl group or a propargyloxycarbonyl group, preferably a C2-6 alkynyloxycarbonyl group; a phenoxycarbonyl group, a naphthoxy
  • the “carbamoyl group having a substituent” in X 1 means that the carbamoyl group is a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C6-10 aryl group, a C6-10 aryl C1-6 alkyl. Or a group to which a 5- to 6-membered heterocyclic group is bonded.
  • a monoalkylcarbamoyl group such as a methylcarbamoyl group, an ethylcarbamoyl group, a dimethylcarbamoyl group, a diethylcarbamoyl group or a dialkylcarbamoyl group, preferably a monoC1-6 alkylcarbamoyl group or a diC1 ⁇ 6 alkylcarbamoyl group; monoarylcarbamoyl group such as phenylcarbamoyl group and 4-methylphenylcarbamoyl group, preferably monoC6-10 arylcarbamoyl group.
  • the “hydroxyl group having a substituent” in X 1 includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, a decyloxy group, a dodecyloxy group, and lauryl.
  • a cycloalkylalkoxy group such as a cyclopropylmethyloxy group and a 2-cyclopentylethyloxy group, preferably a C3-8 cycloalkyl C1-6 alkoxy group; an aralkyloxy group such as a benzyloxy group, preferably a C6-10 aryl C1-6 Alkoxy group; chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, etc.
  • a haloalkoxy group preferably a C1-6 haloalkoxy group; vinyloxy group, 1-propenyloxy group, allyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group, 2-pentenyl group Oxy group, 3-pentenyloxy group, 4-pentenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1-methyl-2 An alkenyloxy group such as a propenyloxy group, a 2-methyl-2-propenyloxy group, a 1-methyl-2-butenyloxy group, or a 2-methyl-2-butenyloxy group, preferably a C2-6 alkenyloxy group;
  • an alkylamino group such as a methylamino group, an ethylamino group, an n-propylamino group, an n-butylamino group, a dimethylamino group or a diethylamino group, preferably a mono-C1-6 alkyl Amino group or di-C1-6 alkylamino group; mono-C1-6 alkylideneamino group such as methylideneamino group, ethylideneamino group; monoarylamino group such as phenylamino group, 4-methylphenylamino group, preferably monoC6-10 Arylamino group; diarylamino group such as di1-naphthylamino group, preferably diC6-10 arylamino group; aralkylamino group such as benzylamino group, preferably C6-10 arylC1-6 alkylamino group; ace
  • an alkylthio group such as a methylthio group and an ethylthio group, preferably a C1-6 alkylthio group
  • an arylthio group such as a phenylthio group and a 4-methylphenylthio group, preferably C6 To 10 arylthio groups
  • acylthio groups such as acetylthio group and benzoylthio group, preferably C1-6 acylthio groups
  • Examples of the “sulfonyl group having a substituent” in X 1 include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, an i-propylsulfonyl group, an n-butylsulfonyl group, an i-butylsulfonyl group, and an s-butyl group.
  • Alkylsulfonyl groups such as sulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, i-pentylsulfonyl group, neopentylsulfonyl group, 1-ethylpropylsulfonyl group, n-hexylsulfonyl group, i-hexylsulfonyl group, Preferably a C1-6 alkylsulfonyl group; a haloalkylsulfonyl group such as a trifluoromethylsulfonyl group, preferably a C1-6 haloalkylsulfonyl group; an arylsulfonyl group such as a phenylsulfonyl group, a 4-methylphenylsulfonyl group, preferably C6-10 arylsulfonyl group;
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • X 1 is preferably a halogeno group or a C1-C8 alkyl group.
  • E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
  • an aromatic hydrocarbon ring such as a benzene ring; a C5-7 cycloalkene ring such as a cyclopentene ring, cyclohexene ring, and cycloheptene ring; a furan ring, a thiophene ring, a pyrrole ring, and an imidazole ring , Pyrazole ring, thiazole ring, oxazole ring, isoxazole ring, isothiazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, azepine ring, diazepine ring and other aromatic 5- to 7-membered heterocycles; .
  • an aromatic hydrocarbon ring such as a benzene ring; a C5-7
  • X 2 each independently represents an unsubstituted or substituted C1-8 alkyl group, an unsubstituted or substituted C2-8 alkenyl group, an unsubstituted or substituted C2-8 alkynyl group, Unsubstituted or substituted C3-8 cycloalkyl group, unsubstituted or substituted C4-8 cycloalkenyl group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted A 5- to 6-membered heterocyclic group having, an unsubstituted or substituted C1-8 acyl group, an unsubstituted or substituted (1-imino) C1-8 alkyl group, an unsubstituted or substituted group Having a carboxyl group, an unsubstituted or substituted carbamoyl group, an unsubstituted or substituted hydroxyl group, an unsubstituted or substituted group An amino
  • C1-8 alkyl group “C2-8 alkenyl group”, “C2-8 alkynyl group”, “C3-8 cycloalkyl group”, “C4-8 cycloalkenyl group”, “C6-10” in X 2
  • Aryl group “5- to 6-membered heterocyclic group”
  • C1-8 acyl group “(1-imino) C1-8 alkyl group”, “carboxyl group having substituent”, “carbamoyl having substituent” “Group”, “hydroxyl group having substituent”, “amino group having substituent”, “mercapto group having substituent”, “sulfonyl group having substituent”, “halogeno group” are those exemplified for X 1 The same thing is mentioned.
  • X 2 is preferably a halogeno group or a C1-8 alkyl group.
  • X represents an oxygen atom, a sulfur atom, a group represented by —C ( ⁇ O) — group, or a group represented by —CHOH— group.
  • X is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • the compound (1) is preferably a compound represented by the formula (2) (hereinafter sometimes referred to as “compound (2)”).
  • a 1 , A 2 , A 3 , and A 4 each independently represent a carbon atom or a nitrogen atom. That is, it forms a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, or a triazine ring.
  • a pyridine ring a pyridine ring in which A 1 is a nitrogen atom is preferable.
  • a 1 , A 2 , A 3 , and A 4 preferably constitute a benzene ring or a pyridine ring.
  • the compound (1) is preferably a compound represented by the formula (3) (hereinafter sometimes referred to as “compound (3)”).
  • n1 represents the number of X 2 and is an integer of 0 to 3, preferably an integer of 0 to 2.
  • a 5 , A 6 , and A 7 each independently represent a carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom.
  • oxygen atoms, sulfur atoms, or a combination of oxygen atoms and sulfur atoms are not adjacent to each other. That is, the ring containing A 5 , A 6 , and A 7 constitutes a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a thiazole ring, an oxazole ring, an isoxazole ring, and an isothiazole ring.
  • the pyrazole ring is preferably a pyrazole ring in which A 6 and A 7 are nitrogen atoms.
  • the thiophene ring a thiophene ring in which A 7 is a sulfur atom is preferable.
  • the compound (1) is preferably a compound represented by the formula (4) (hereinafter sometimes referred to as “compound (4)”).
  • Cy, D, X 1, m, X 2, and n have the same meanings as each of the above formulas (1).
  • D an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable.
  • the compound (4) is preferably a compound having a quinoline ring.
  • the salt or N-oxide compound of the nitrogen-containing heterocyclic compound according to the present invention is not particularly limited as long as it is an agricultural and horticulturally acceptable salt or N-oxide compound.
  • the salt include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; Examples include salts of transition metals such as iron and copper; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, and hydrazine.
  • the nitrogen-containing heterocyclic compound according to the present invention can be produced, for example, by the synthesis method shown below.
  • X 1 , X 2 , D, m, n, Q, and R represent the same meaning as described above.
  • R, X 1 , X 2 , D, Q, m, and n represent the same meaning as described above.
  • the salt of the compound according to the present invention can be prepared by bringing an inorganic acid compound, an organic acid compound, an alkali metal compound, an alkaline earth metal compound, a transition metal compound, an ammonium compound or the like into contact with the compound (1).
  • the N-oxide compound according to the present invention can be prepared by a known oxidation reaction. For example, it can be prepared by bringing compound (1) into contact with a peroxide such as hydrogen peroxide in a solvent or without a solvent.
  • the target product can be efficiently isolated by subjecting it to conventional post-treatment operations in synthetic organic chemistry and, if necessary, conventionally known separation and purification means.
  • the structure of the target product can be identified and confirmed by measurement of 1 H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis, or the like.
  • the agricultural and horticultural fungicide according to the present invention contains at least one selected from the nitrogen-containing heterocyclic compound or its salt or N-oxide compound according to the present invention as an active ingredient. .
  • the agricultural and horticultural fungicides of the present invention belong to a wide variety of filamentous fungi, for example, algae fungi (Oomycetes), Ascomycetes, Deuteromycetes, and Basidiomycetes Has excellent bactericidal power against bacteria.
  • algae fungi Oomycetes
  • Ascomycetes Ascomycetes
  • Deuteromycetes Deuteromycetes
  • Basidiomycetes Has excellent bactericidal power against bacteria.
  • the agricultural and horticultural fungicide of the present invention is used in methods such as seed treatment, foliage application, soil application, and water surface application for the control of various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf, and grass. can do.
  • Sugar beet brown spot (Cercospora beticola), black root (Aphanomyces cochlloides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris);
  • Peanut brown spot (Mycosphaerella arachidis), black astringency (Mycosphaerella berkeleyi);
  • Cucumber powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), mycorrhizal disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea) Anthracnose (Colletotrichum orbiculare), black spot (Cladosporium cucumerinum), brown spot (Corynespora cassicola), seedling blight (Pyth
  • Tomato gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans); Eggplant: gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew (Erysiphe cichoracearum), subtle mold (Mycovellosiella nattrassii);
  • Barley leafy leaf disease (Pyrenophora graminea), cloud shape disease (Rhynchosporium secalis), naked smut (Ustilago tritici, U.nuda); Rice: Rice Blast (Pyricularia oryzae), Rhizoctonia solani, Idiot Seedling (Gibberella fujikuroi), Sesame Leaf Blight (Cochliobolus miyabeanus), Seedling Blight (Pythium graminicolum), White Leaf Blight (Xanthomonas oryzae) Bacterial disease (Burkholderia plantarii), Brown disease (Acidovorax avenae), Bacterial disease (Burkholderia glumae); Tobacco: Sclerotinia sclerotiorum, powdery mildew (Erysiphe cichoracearum); Tulip: Gray mold disease (Botrytis cinerea); Bentgrass: Scle
  • the agricultural and horticultural fungicide of the present invention has an excellent bactericidal effect against resistant bacteria.
  • the resistant bacteria include gray mold fungus (Botrytis cinerea), sugar beet brown fungus (Cercospora beticola), apple black rot fungus (Venturia inaequalis), pear black scab (Venturia nashicola); a gray mold fungus (Botrytis cinerea) resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione) and the like.
  • dicarboximide fungicides for example, vinclozolin, procymidone, iprodione
  • More preferable diseases to which the agricultural and horticultural fungicide of the present invention is applied include black scab of apple, gray mold of cucumber, powdery mildew of wheat, plague of tomato, leaf rust of wheat, rice blast of rice, cucumber Examples include vine split disease.
  • the agricultural and horticultural fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
  • the agricultural and horticultural fungicide of the present invention should be used in the form that can be taken as an agrochemical, that is, in the form of an agrochemical formulation such as a wettable powder, a granule, a powder, an emulsion, an aqueous solvent, a suspension, or a granular wettable powder. Can do.
  • Additives and carriers used in solid formulations include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, clay, sodium benzoate, urea And organic and inorganic compounds such as mirabilite.
  • Solvents used in liquid formulations include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water, etc. Can be mentioned.
  • a surfactant can be added as necessary.
  • the surfactant that can be added is not particularly limited.
  • alkyl phenyl ether added with polyoxyethylene alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, sorbitan higher fatty acid ester added with polyoxyethylene, tristyryl added with polyoxyethylene
  • Nonionic surfactants such as phenyl ether, sulfates of alkylphenyl ethers added with polyoxyethylene, alkylbenzene sulfonates, sulfates of higher alcohols, alkylnaphthalene sulfonates, polycarboxylates, lignin sulfones Acid salt, formaldehyde condensate of alkyl naphthalene sulfonate, and isobutylene-maleic anhydride copolymer.
  • the wettable powder, emulsion, flowable powder, aqueous solvent, or granular wettable powder thus obtained is diluted with water to a predetermined concentration and sprayed on plants as a solution, suspension or emulsion. Can be used. In addition, powders and granules can be used by spraying them on plants as they are.
  • the amount of the active ingredient in the agricultural and horticultural fungicide of the present invention is preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.
  • the application amount of the agricultural and horticultural fungicide of the present invention varies depending on weather conditions, formulation form, application time, application method, application place, disease to be controlled, target crop, etc., but it is usually 1 in terms of the amount of active ingredient compound per hectare. ⁇ 1,000 g, preferably 10 to 100 g.
  • the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
  • the agricultural and horticultural fungicide of the present invention may be mixed with other fungicides, insecticides / acaricides, and synergists.
  • the agricultural and horticultural fungicide of the present invention and other fungicides, insecticides / acaricides, and synergists can be used simultaneously or in succession. Representative examples of other fungicides, insecticides, acaricides, and plant growth regulators that can be used in this manner are shown below.
  • Fungicide (1) benzimidazole series: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl, chlorphenazole; (2) Dicarboximide type: Clozolinate, iprodione, procymidone, vinclozolin; (3) DMI-bactericidal system: imazalyl, oxpoconazole, pefazoate, prochloraz, triflumizole, trifolin, pyrifenox, phenarimol, nuarimol, azaconazole, viteltanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, Epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafor, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole
  • Phenylamide Benalaxyl, Benalaxyl-M, Cloziracone, Furaraxyl, Metalaxyl, Metalaxyl-M, Oxadixyl, Offrase; (5) Amine-based: aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; (6) phosphorothiolate type: EDDP, iprobenphos, pyrazophos; (7) Dithiolane type: isopropylthiolane; (8) Carboxamides: benodanyl, boscalid, carboxin, fenfuran, flutolanil, furamethpyr, mepronil, oxycarboxin, pentiopyrad, tifluzamide, bixaphene, isopyrazam, penflufen, floxapyroxide, sedaxane; (9) Hydroxy- (2-amino
  • AP fungicide (anilinopyrimidine) type cyprodinil, mepanipyrim, pyrimethanyl, and prim;
  • N-phenylcarbamate system Dietophenecarb;
  • QoI-bactericidal (Qo inhibitor) system azoxystrobin, picoxystrobin, pyraclostrobin, cresoxime-methyl, trifloxystrobin, dimoxystrobin, metminostrobin, orizastrobin, Famoxadone, fluoxastrobin, fenamidone, metminophen; amethoctrazine, pyramethostrobin, pyroxystrobin, pyribencarb; cumethoxystrobin, cumoxystrobin, enestrobrin, phenoxystrobin, triclopyricarb; (13) PP fungicide (phenylpyrrole) system: fenpiconyl, fludioxonil; (14) Quinoline series
  • AH fungicide (aromatic hydrocarbon) type biphenyl, chloronebu, dichlorane, kintozen, technazen, tortofos-methyl; (16) MBI-R system: fusaride, pyroxylone, tricyclazole; (17) MBI-D system: carpropamide, diclocimet, phenoxanyl; (18) SBI agent: fenhexamide, pyributicalbu, turbinafine; (19) Phenylurea: Pencyclone; (20) QiI-fungicide (Qi inhibitor): cyazofamide, amisulbrom, flumeciclox; (21) Benzamide series: Zoxamide; (22) Enopyranuron series: blastcidin, mildiomycin; (23) Hexopyranosyl system: Kasugamycin, Kasugamycin hydrochloride; (24) Glucopyranosyl system: streptomycin, validamycin, validamycin A; (25) Cyanoacetamide series
  • Phosphate ester phosphorous acid, torquelophosmethyl, fosetyl, torquetophosmethyl;
  • Phthalamic acid type Teclophthalam;
  • Benzotriazine type triazoxide;
  • benzenesulfonamide series fursulfamide;
  • Pyridazinone Dichromedin;
  • CAA fungicide (carboxylic acid amide) system dimethomorph, furmorph, benavalicarb-isopropyl, iprovaricarb, mandipropamide, variphenate;
  • Tetracycline oxytetracycline;
  • (36) Thiocarbamate system metasulfocarb;
  • Resistance inducer acibenzoral S methyl, probenazole, thiazinyl, isothianyl;
  • Other compounds etridiazole, polyoxin, polyoxorim, oxolinic acid, hydroxyisoxazole, octirin
  • Nicotine receptor agonist / antagonist compounds acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nithiazine, nicotine, bensultap, cartap, flupiradiflon;
  • GABA antagonist compound (A) acetoprole, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole; (B) Organochlorine: camfechlor, chlordane, endosulfan, HCH, ⁇ -HCH, heptachlor, methoxychlor; (7) Macrocyclic lactone insecticide: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomectin,
  • Oxidative phosphorylation inhibitor compounds cyhexatin, diafenthiuron, phenbutatin oxide, propargite, azocyclotin; (12) molting disrupting compound: cyromazine; (13) Mixed function oxidase inhibitor compound: piperonyl butoxide; (14) Sodium channel blocker compounds: indoxacarb, metaflumizone; (15) Microbial pesticides: BT agent, entomopathogenic virus agent, entomopathogenic fungus agent, nematode pathogenic fungus agent; Bacillus spp., White scab fungus, black scab fungus, Pekirmyces spp., Thuringiensins, Vertici Lilium species; (16) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside; (17) Octopaminergic agent:
  • Plant growth regulator Abscisic acid, indole butyric acid, uniconazole, etiquelozate, etephone, cloxiphonac, chlormecote, chlorella extract, calcium peroxide, cyanamide, dichlorprop, gibberellin, daminozide, decyl alcohol, trinexapac ethyl, mepicoat chloride, pack Lobutrazole, paraffin wax, piperonyl butoxide, pyraflufenethyl, flurprimidol, prohydrojasmon, prohexadione calcium salt, benzylaminopurine, pendimethalin, forchlorphenuron, potassium maleate hydrazide, 1-naphthyl Acetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride;
  • Tables 1 to 4 show the nitrogen-containing heterocyclic compounds obtained in the above Examples and the nitrogen-containing heterocyclic compounds that can be synthesized by the same method as in any of the above Examples.
  • the symbols in the table are substituents of the compounds represented by formulas (5) to (8).
  • Py means pyridine.
  • melting point (° C.) melting point (° C.)
  • refractive index (nD) refractive index (nD)
  • Amr. Means amorphous and Oil means oil at normal temperature
  • Compound 1-11 1.37 (s, 6H), 3.07 (s, 2H), 6.87 (d, 1H), 7.06 (t, 1H), 7.27-7.51 (m, 5H), 8.83 (d, 1H)
  • Compound 1-13 0.31 (s, 9H), 2.69 (s, 3H), 6.64 (s, 1H), 6.88 (d, 1H), 7.11 (t, 1H), 7.25-7.46 (m, 5H)
  • Compound 1-15 3.95 (t, 2H), 4.28 (t, 2H), 6.88 (d, 1H), 7.05 (t, 1H), 7.29-7.53 (m, 5H), 8.87 (d, 1H).
  • Compound 1-17 4.65 (dd, 1H), 4.83 (dd, 1H), 6.21 (t, 1H), 6.74 (d, 1H), 6.99 (t, 1H), 7.37-7.53 (m, 4H), 7.69 (d, 1H), 8.83 (d, 1H).
  • Compound 1-20 2.73 (s, 3H), 6.61 (t, 1H), 6.86 (d, 1H), 7.12 (t, 1H), 7.25-7.49 (m, 5H), 8.45 d, 1H).
  • Formulation Example 3 Dust The nitrogen-containing heterocyclic compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.
  • Formulation Example 4 Granules Nitrogen-containing heterocyclic compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part The above was pulverized and mixed well, and water was added and kneaded well. Thereafter, granulation and drying are performed to obtain a granule containing 5% of the active ingredient.
  • Nitrogen-containing heterocyclic compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts Wet mill until the particle size is 3 microns or less to obtain a 10% active ingredient suspension.
  • Formulation Example 6 Granule wettable powder Nitrogen-containing heterocyclic compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Ligninsulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts After the above is uniformly mixed and finely pulverized, an appropriate amount of water is added and then kneaded to form a clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.

Abstract

Cette invention concerne : un composé hétérocyclique azoté représenté par la formule (1) ou un sel ou un composé de N-oxyde de celui-ci ; et un agent bactéricide à visée agricole et horticole, qui comprend au moins un composant choisi parmi les composés précités à titre de principe actif. Dans la formule, Cy représente un groupe hétérocyclique ayant de 5 à 6 chaînons ou autre ; X1 et X2 représentent indépendamment un groupe halogéno ou autre ; et m et n représentent le nombre de X1 substitués et le nombre de X2 substitués, respectivement.
PCT/JP2012/076767 2011-10-17 2012-10-17 Composé hétérocyclique azoté, et agent bactéricide à visée agricole et horticole WO2013058256A1 (fr)

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WO2018197692A1 (fr) 2017-04-27 2018-11-01 Bayer Aktiengesellschaft Hétéroarylphénylaminoquinoléines et analogues
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WO2020079173A1 (fr) 2018-10-18 2020-04-23 Bayer Aktiengesellschaft Pyridylphénylaminoquinolines et analogues
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WO2021083936A1 (fr) * 2019-11-01 2021-05-06 Syngenta Crop Protection Ag Composés hétéroaromatiques bicycliques fusionnés à action pesticide
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US10647675B2 (en) 2015-09-18 2020-05-12 Kaken Pharmaceutical Co., Ltd. Biaryl derivative and medicine containing same
WO2017072283A1 (fr) 2015-10-29 2017-05-04 Bayer Cropscience Aktiengesellschaft Hétérocycles silylphénoxy trisubstitués et analogues
KR102554993B1 (ko) 2017-04-27 2023-07-12 바이엘 악티엔게젤샤프트 헤테로아릴페닐아미노퀴놀린 및 유사체
CN110603253A (zh) * 2017-04-27 2019-12-20 拜耳公司 杂芳基苯基氨基喹啉及类似物
KR20190141734A (ko) * 2017-04-27 2019-12-24 바이엘 악티엔게젤샤프트 헤테로아릴페닐아미노퀴놀린 및 유사체
US11457629B2 (en) 2017-04-27 2022-10-04 Bayer Aktiengesellschaft Heteroarylphenylaminoquinolines and analogues
CN110603253B (zh) * 2017-04-27 2023-01-20 拜耳公司 杂芳基苯基氨基喹啉及类似物
WO2018197692A1 (fr) 2017-04-27 2018-11-01 Bayer Aktiengesellschaft Hétéroarylphénylaminoquinoléines et analogues
JP2020517685A (ja) * 2017-04-27 2020-06-18 バイエル・アクチエンゲゼルシヤフト ヘテロアリールフェニルアミノキノリン類及び類似体
TWI782983B (zh) * 2017-04-27 2022-11-11 德商拜耳廠股份有限公司 雜芳基苯基胺基喹啉及類似物
JP7157077B2 (ja) 2017-04-27 2022-10-19 バイエル・アクチエンゲゼルシヤフト ヘテロアリールフェニルアミノキノリン類及び類似体
WO2018202706A1 (fr) 2017-05-03 2018-11-08 Bayer Aktiengesellschaft Silylhétéroaryloxyquinoléines trisubstituées et analogues
WO2019065516A1 (fr) * 2017-09-26 2019-04-04 日本曹達株式会社 Composé quinoléine, et agent bactéricide pour application agricole et horticole
WO2020079167A1 (fr) 2018-10-18 2020-04-23 Bayer Aktiengesellschaft Hétéroarylaminoquinolines et analogues
WO2020079173A1 (fr) 2018-10-18 2020-04-23 Bayer Aktiengesellschaft Pyridylphénylaminoquinolines et analogues
WO2020079232A1 (fr) 2018-10-20 2020-04-23 Bayer Aktiengesellschaft Oxétanylphénoxyquinolines et analogues
WO2021083936A1 (fr) * 2019-11-01 2021-05-06 Syngenta Crop Protection Ag Composés hétéroaromatiques bicycliques fusionnés à action pesticide
WO2021209490A1 (fr) 2020-04-16 2021-10-21 Bayer Aktiengesellschaft Cyclaminephénylaminoquinoléines utiles en tant que fongicides

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