WO2013058256A1 - Nitrogenated heterocyclic compound, and bactericidal agent for agricultural and horticultural purposes - Google Patents

Nitrogenated heterocyclic compound, and bactericidal agent for agricultural and horticultural purposes 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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Priority to JP2013539651A priority Critical patent/JP5729889B2/en
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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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    • 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

Provided are: a nitrogenated heterocyclic compound represented by formula (1) or a salt or N-oxide compound thereof; and a bactericidal agent for agricultural and horticultural purposes, which comprises at least one component selected from the above-mentioned compounds as an active ingredient. In the formula, Cy represents a 5- to 6-membered heterocyclic group or the like; X1 and X2 independently represent a halogeno group or the like; and m and n represent the number of substituted X1's and the number of substituted X2's, respectively.

Description

含窒素ヘテロ環化合物および農園芸用殺菌剤Nitrogen-containing heterocyclic compounds and agricultural and horticultural fungicides
　本発明は、含窒素ヘテロ環化合物またはその塩若しくはＮ－オキサイド化合物に関する。より詳細に、本発明は、効果が確実で安全に使用できる農園芸用殺菌剤、および農園芸用殺菌剤の有効成分として有用な含窒素ヘテロ環化合物またはその塩若しくはＮ－オキサイド化合物に関する。
　本願は、２０１１年１０月１７日に日本に出願された特願２０１１－２２８３７３号に基づき優先権を主張し、その内容をここに援用する。 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.
　農園芸作物の病害に対して多数の防除薬剤が知られている。しかし、従来の防除薬剤の多くは、その防除効力が不十分であったり、薬剤耐性の病原菌の出現によりその使用が制限されたり、植物体に薬害や汚染を生じさせたり、若しくは人畜魚類に対する毒性や環境への影響が大きかったりなどで、十分に満足できるものではなかった。そのため、かかる欠点の少ない薬剤の出現が強く要望されている。 Many control agents are known for diseases of agricultural and horticultural crops. However, many of the conventional control chemicals have insufficient control efficacy, their use is limited by the emergence of drug-resistant pathogens, cause phytotoxicity and pollution to plants, or are toxic to human and livestock fish. And the impact on the environment was not enough. For this reason, there is a strong demand for the appearance of drugs with few such defects.
　特許文献１～３には、本発明化合物と類似の化学構造を有するキノリン誘導体、およびそれを有効成分として含有する農園芸用殺菌剤が開示されている。 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.
ＷＯ２００５／０７０９１７号パンフレットWO2005 / 0700917 pamphlet ＷＯ２００７／０１１０２２号パンフレットWO2007 / 011022 pamphlet ＷＯ２０１１／０８１１７４号パンフレットWO2011 / 081174 pamphlet
　本発明は、効果が確実で安全に使用できる農園芸用殺菌剤、および農園芸用殺菌剤の有効成分として有用な含窒素ヘテロ環化合物またはその塩若しくはＮ－オキサイド化合物を提供することを課題とする。 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.
　本発明は以下の態様を包含するものである。
〔１〕　式（１）で表される含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物。 The present invention includes the following aspects.
[1] A nitrogen-containing heterocyclic compound represented by the formula (1), a salt thereof or an N-oxide compound.
Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005
　上記の式（１）中、Ｃｙは、無置換の若しくは置換基を有するオキシラニル基、または無置換の若しくは置換基を有する５～６員ヘテロ環基を示す。
　Ｂは、窒素原子または炭素原子を示す。
　Ｄは、５～７員炭化水素環または５～７員ヘテロ環を示す。
　Ｘ１は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有する５～６員ヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。ｍは、Ｘ１の個数を示し、０～６のいずれかの整数である。
　Ｅは、５～７員炭化水素環または５～７員ヘテロ環を示す。
　Ｘ２は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有する５～６員ヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。ｎは、Ｘ２の個数を示し、０～４のいずれかの整数である。
　Ｘは、酸素原子、硫黄原子、－Ｃ（＝Ｏ）－基で表される基、または－ＣＨＯＨ－基で表される基を示す。
〔２〕　上記の式（１）が、式（２）で表されることを特徴とする上記〔１〕に記載の含窒素ヘテロ環化合物またはその塩若しくはＮ－オキサイド化合物。 In the above formula (1), 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 unsubstituted or substituted mercapto group, a substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group is shown. 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 carboxyl group, an unsubstituted or substituted carbamoyl group, an unsubstituted or substituted hydroxyl group, an unsubstituted or substituted group An amino group, an unsubstituted or substituted mercapto group, a substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group is shown. 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.
[2] The nitrogen-containing heterocyclic compound, the salt thereof or the N-oxide compound according to [1], wherein the formula (1) is represented by the formula (2).
Figure JPOXMLDOC01-appb-C000006
Figure JPOXMLDOC01-appb-C000006
　上記の式（２）中、Ｃｙ、Ｘ１、ｍ、Ｘ２、ｎ、Ｂ、およびＸは、上記の式（１）中のそれぞれと同じ意味を示す。
　Ａ１、Ａ２、Ａ３、およびＡ４は、それぞれ独立して、炭素原子または窒素原子を示す。
〔３〕　上記の式（１）が、式（３）で表されることを特徴とする上記〔１〕に記載の含窒素ヘテロ環化合物またはその塩若しくはＮ－オキサイド化合物。 In said formula (2), 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.
[3] The nitrogen-containing heterocyclic compound, the salt thereof or the N-oxide compound according to [1], wherein the formula (1) is represented by the formula (3).
Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007
　上記の式（３）中、Ｃｙ、Ｘ１、ｍ、Ｘ２、Ｂ、およびＸは、上記の式（１）中のそれぞれと同じ意味を示す。ｎ１は、Ｘ２の個数を示し、０～３のいずれかの整数である。
　Ａ５、Ａ６、およびＡ７は、それぞれ独立して、炭素原子、窒素原子、酸素原子、または硫黄原子を示す。ただし、酸素原子同士、硫黄原子同士、酸素原子と硫黄原子の組合わせが隣接することはない。
〔４〕　上記の式（１）が、式（４）で表される上記〔１〕に記載の含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物。 In said formula (3), Cy, X < 1 >, m, X < 2 >, B, and X show the same meaning as each in said formula (1). 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.
[4] The nitrogen-containing heterocyclic compound of the above-mentioned [1], wherein the above formula (1) is represented by the formula (4), or a salt or N-oxide compound thereof.
Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008
　上記の式（４）中、Ｃｙ、Ｄ、Ｘ１、ｍ、Ｘ２、およびｎは、上記の式（１）中のそれぞれと同じ意味を示す。 In the above formula (4), Cy, D, X 1, m, X 2, and n have the same meanings as each of the above formulas (1).
〔５〕　式（４）中のＤがベンゼン環である、上記〔４〕に記載の含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物。
〔６〕　Ｃｙが、無置換の若しくは置換基を有するオキシラニル基、無置換の若しくは置換基を有する５員ヘテロアリール基、無置換の若しくは置換基を有する６員へテロアリール基、無置換の若しくは置換基を有する部分不飽和の５員ヘテロ環基、無置換の若しくは置換基を有する部分不飽和の６員へテロ環基、無置換の若しくは置換基を有する飽和５員ヘテロ環基、または無置換の若しくは置換基を有する飽和６員へテロ環基である、上記の〔１〕～〔５〕のいずれかひとつに記載の含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物。
〔７〕　上記の〔１〕～〔６〕のいずれかひとつに記載の含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物から選ばれる少なくとも１種を有効成分として含有する農園芸用殺菌剤。
[5] The nitrogen-containing heterocyclic compound according to [4], or a salt or N-oxide compound thereof, wherein D in the formula (4) is a benzene ring.
[6] Cy is unsubstituted or substituted oxiranyl group, unsubstituted or substituted 5-membered heteroaryl group, unsubstituted or substituted 6-membered heteroaryl group, unsubstituted or substituted A partially unsaturated 5-membered heterocyclic group having a group, an unsubstituted or substituted partially unsaturated 6-membered heterocyclic group, an unsubstituted or substituted saturated 5-membered heterocyclic group, or unsubstituted Or a nitrogen-containing heterocyclic compound or a salt or N-oxide compound thereof according to any one of the above [1] to [5], which is a saturated 6-membered heterocyclic group having a substituent.
[7] An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the nitrogen-containing heterocyclic compound according to any one of [1] to [6] above, a salt thereof, or an N-oxide compound .
　本発明の含窒素ヘテロ環化合物は、農園芸用殺菌剤の有効成分として有用な新規化合物である。本発明の農園芸用殺菌剤は、確実で優れた防除効果を有し、植物体に薬害を生じることがなく、人畜魚類に対する毒性や環境への影響が少ない、安全な薬剤である。 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.
　本発明者らは、式（１）～式（４）で表される含窒素ヘテロ環化合物の含窒素ヘテロ環化合物は農園芸用殺菌剤の有効成分として効果が確実で安全に使用できることを見出し、当該知見に基づきさらに検討を重ね本発明を完成するに至った。 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.
　以下、本発明を、１）含窒素ヘテロ環化合物と、２）農園芸用殺菌剤とに項分けして詳細に説明する。 Hereinafter, the present invention will be described in detail by dividing it into 1) nitrogen-containing heterocyclic compounds and 2) agricultural and horticultural fungicides.
１）含窒素ヘテロ環化合物
〔式（１）で表される化合物〕
　本発明に係る含窒素ヘテロ環化合物は、式（１）で表される化合物（以下、「化合物（１）」と表記することがある。）、またはその塩若しくはＮ－オキサイド化合物である。 1) 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.
Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009
　本発明に係る含窒素ヘテロ環化合物には、水和物、各種溶媒和物や結晶多形などが含まれる。さらに、本発明に係る含窒素ヘテロ環化合物は、不斉炭素原子、二重結合などに基づく立体異性体およびそれらの混合物を包含する。 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.
　まず、式（１）における、「無置換の」および「置換基を有する」の意味を説明する。
　「無置換の」の用語は、母核となる基のみであることを意味する。「置換基を有する」との記載がなく母核となる基の名称のみで記載しているときは、別段の断りがない限り「無置換の」意味である。
　一方、「置換基を有する」の用語は、母核となる基のいずれかの水素原子が、母核と同種または異種の構造の基で置換されていることを意味する。従って、「置換基」は、母核となる基に結合した他の基である。置換基は１つであってもよいし、２つ以上であってもよい。２つ以上の置換基は同一であってもよいし、異なるものであってもよい。
　「Ｃ１～６」などの用語は、母核となる基の炭素原子数が１～６個などであることを表している。この炭素原子数には、置換基の中に在る炭素原子の数を含まない。例えば、置換基としてエトキシ基を有するブチル基は、Ｃ２アルコキシＣ４アルキル基に分類する。 First, the meanings of “unsubstituted” and “having a substituent” in formula (1) will be described.
The term “unsubstituted” means only the group that is the mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
On the other hand, 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.
　「置換基」は化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。
　「置換基」となり得る基としては、　フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；　シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；　ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などのＣ２～６アルケニル基；　２－シクロプロペニル基、２－シクロペンテニル基、３－シクロヘキセニル基などのＣ３～６シクロアルケニル基；　エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などのＣ２～６アルキニル基； The “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Examples of 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; C3-6 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group Ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl Group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group A C2-6 alkynyl group such as;
　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；　ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などのＣ２～６アルケニルオキシ基；　エチニルオキシ基、プロパルギルオキシ基などのＣ２～６アルキニルオキシ基；　フェニル基、ナフチル基などのＣ６～１０アリール基；　フェノキシ基、１－ナフトキシ基などのＣ６～１０アリールオキシ基；　ベンジル基、フェネチル基などのＣ７～１１アラルキル基；　ベンジルオキシ基、フェネチルオキシ基などのＣ７～１１アラルキルオキシ基；　ホルミル基、アセチル基、プロピオニル基、ベンゾイル基、シクロヘキシルカルボニル基などのＣ１～７アシル基；　ホルミルオキシ基、アセチルオキシ基、プロピオニルオキシ基、ベンゾイルオキシ基、シクロヘキシルカルボニルオキシ基などのＣ１～７アシルオキシ基；　メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などのＣ１～６アルコキシカルボニル基；　カルボキシル基； 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 acyl groups; C1-7 acyloxy groups such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i- C1-6 alkoxycarbonyl groups such as propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group; carboxyl group;
　水酸基；　オキソ基（　＝Ｏ）；　クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基、パーフルオロ－ｎ－ペンチル基などのＣ１～６ハロアルキル基；　２－クロロ－１－プロペニル基、２－フルオロ－１－ブテニル基などのＣ２～６ハロアルケニル基；　４，４－ジクロロ－１－ブチニル基、４－フルオロ－１－ペンチニル基、５－ブロモ－２－ペンチニル基などのＣ２～６ハロアルキニル基；　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基などのＣ１～６ハロアルコキシ基；　２－クロロプロペニルオキシ基、３－ブロモブテニルオキシ基などのＣ２～６ハロアルケニルオキシ基；　４－クロロフェニル基、４－フルオロフェニル基、２，４－ジクロロフェニル基などのＣ６～１０ハロアリール基；　４－フルオロフェニルオキシ基、４－クロロ－１－ナフトキシ基などのＣ６～１０ハロアリールオキシ基；　クロロアセチル基、トリフルオロアセチル基、トリクロロアセチル基、４－クロロベンゾイル基などのＣ１～７ハロアシル基； Hydroxyl group; 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; chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4 A C1-7 haloacyl group such as a chlorobenzoyl group;
　シアノ基；　イソシアノ基；　ニトロ基；　イソシアナト基；　シアナト基；　アジド基；　アミノ基；　メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのＣ１～６アルキルアミノ基；　アニリノ基、ナフチルアミノ基などのＣ６～１０アリールアミノ基；　ベンジルアミノ基、フェニルエチルアミノ基などのＣ７～１１アラルキルアミノ基；　ホルミルアミノ基、アセチルアミノ基、プロパノイルアミノ基、ブチリルアミノ基、ｉ－プロピルカルボニルアミノ基、ベンゾイルアミノ基などのＣ１～７アシルアミノ基；　メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、ｎ－プロポキシカルボニルアミノ基、ｉ－プロポキシカルボニルアミノ基などのＣ１～６アルコキシカルボニルアミノ基；　カルバモイル基；　ジメチルカルバモイル基、フェニルカルバモイル基、Ｎ－フェニル－Ｎ－メチルカルバモイル基などの置換カルバモイル基；　イミノメチル基、（１－イミノ）エチル基、（１－イミノ）－ｎ－プロピル基などのイミノＣ１～６アルキル基；　ヒドロキシイミノメチル基、（１－ヒドロキシイミノ）エチル基、（１－ヒドロキシイミノ）プロピル基などのヒドロキシイミノＣ１～６アルキル基；メトキシイミノメチル基、（１－メトキシイミノ）エチル基などのＣ１～６アルコキシイミノＣ１～６アルキル基； Cyano group; isocyano group; nitro group; isocyanato group; cyanato group; azide group; amino group; C1-6 alkylamino group such as methylamino group, dimethylamino group and diethylamino group; C6 ~ such as anilino group and naphthylamino group 10 arylamino group; C7-11 aralkylamino group such as benzylamino group and phenylethylamino group; formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group, etc. 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. A C1-6 alkoxyimino C1-6 alkyl group;
　メルカプト基；　イソチオシアナト基；　チオシアナト基；　メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｉ－プロピルチオ基、ｎ－ブチルチオ基、ｉ－ブチルチオ基、ｓ－ブチルチオ基、ｔ－ブチルチオ基などのＣ１～６アルキルチオ基；　ビニルチオ基、アリルチオ基などのＣ２～６アルケニルチオ基；　エチニルチオ基、プロパルギルチオ基などのＣ２～６アルキニルチオ基；　フェニルチオ基、ナフチルチオ基などのＣ６～１０アリールチオ基；　チアゾリルチオ基、ピリジルチオ基などのヘテロアリールチオ基；　ベンジルチオ基、フェネチルチオ基などのＣ７～１１アラルキルチオ基；　（メチルチオ）カルボニル基、（エチルチオ）カルボニル基、（ｎ－プロピルチオ）カルボニル基、（ｉ－プロピルチオ）カルボニル基、（ｎ－ブチルチオ）カルボニル基、（ｉ－ブチルチオ）カルボニル基、（ｓ－ブチルチオ）カルボニル基、（ｔ－ブチルチオ）カルボニル基などの（Ｃ１～６アルキルチオ）カルボニル基； Mercapto group; isothiocyanato group; thiocyanato group; C1-6 alkylthio such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group Groups: C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio groups and propargylthio groups; C6-10 arylthio groups such as phenylthio groups and naphthylthio groups; thiazolylthio groups and pyridylthio groups Heteroarylthio groups of C7-11 aralkylthio groups such as benzylthio group and phenethylthio group; (methylthio) carbonyl group, (ethylthio) carbonyl group, (n-propylthio) carbonyl group, (i-propylthio) carbo Le group, (n- butylthio) carbonyl group, (i-butylthio) carbonyl group, (s-butylthio) carbonyl group, (t-butylthio) (C1 ~ 6 alkylthio), such as a carbonyl group a carbonyl group;
　メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などのＣ１～６アルキルスルフィニル基；　アリルスルフィニル基などのＣ２～６アルケニルスルフィニル基；　プロパルギルスルフィニル基などのＣ２～６アルキニルスルフィニル基；　フェニルスルフィニル基などのＣ６～１０アリールスルフィニル基；　チアゾリルスルフィニル基、ピリジルスルフィニル基などのヘテロアリールスルフィニル基；　ベンジルスルフィニル基、フェネチルスルフィニル基などのＣ７～１１アラルキルスルフィニル基；　メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などのＣ１～６アルキルスルホニル基；　アリルスルホニル基などのＣ２～６アルケニルスルホニル基；　プロパルギルスルホニル基などのＣ２～６アルキニルスルホニル基；　フェニルスルホニル基などのＣ６～１０アリールスルホニル基；　チアゾリルスルホニル基、ピリジルスルホニル基などのヘテロアリールスルホニル基；　ベンジルスルホニル基、フェネチルスルホニル基などのＣ７～１１アラルキルスルホニル基； 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. C6-10 arylsulfinyl group of the above; heteroarylsulfinyl group such as thiazolylsulfinyl group, pyridylsulfinyl group; C7-11 aralkylsulfinyl group such as benzylsulfinyl group, phenethylsulfinyl group; methylsulfonyl group, ethylsulfonyl group, t- C1-6 alkylsulfonyl groups such as butylsulfonyl group; C2-6 alkenylsulfonyl groups such as allylsulfonyl group; propargylsulfonyl group C2-6 alkynylsulfonyl groups of C6-10 arylsulfonyl groups such as phenylsulfonyl groups; heteroarylsulfonyl groups such as thiazolylsulfonyl groups and pyridylsulfonyl groups; C7-11 aralkylsulfonyl groups such as benzylsulfonyl groups and phenethylsulfonyl groups Group;
　ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員ヘテロアリール基；　ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員ヘテロアリール基；　ピロリジニル基、テトラヒドロフラニル基、ピペリジル基、ピペラジニル基、モルホリニル基などの飽和ヘテロ環基；　トリメチルシリル基、トリエチルシリル基、ｔ－ブチルジメチルシリル基などのトリＣ１～６アルキルシリル基；　トリフェニルシリル基；などを挙げることができる。 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.
　また、これらの「置換基」はそれの中にさらに別の「置換基」を有するものであってもよい。例えば、置換基としてのブチル基に、別の置換基としてエトキシ基を有するもの、すなわち、エトキシブチル基のようなものであってもよい。 These “substituents” may have another “substituent” therein. For example, a butyl group as a substituent and an ethoxy group as another substituent, that is, an ethoxybutyl group may be used.
〔Ｃｙ〕
　Ｃｙは、無置換の若しくは置換基を有するオキシラニル基、または無置換の若しくは置換基を有する５～６員ヘテロ環基を示す。
　「５～６員ヘテロ環基」は、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環の構成原子として含むものである。
　Ｃｙとしては、無置換の若しくは置換基を有するオキシラニル基、無置換の若しくは置換基を有する５員ヘテロアリール基、無置換の若しくは置換基を有する６員へテロアリール基、無置換の若しくは置換基を有する部分不飽和の５員ヘテロ環基、無置換の若しくは置換基を有する部分不飽和の６員へテロ環、基無置換の若しくは置換基を有する飽和５員ヘテロ環基、または無置換の若しくは置換基を有する飽和６員へテロ環基であることが好ましい。 [Cy]
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員ヘテロアリール基としては、　ピロール－１－イル基、ピロール－２－イル基、ピロール－３－イル基などのピロリル基；　フラン－２－イル基、フラン－３－イル基などのフリル基；　チオフェン－２－イル基、チオフェン－３－イル基などのチエニル基；　イミダゾール－１－イル基、イミダゾール－２－イル基、イミダゾール－４－イル基、イミダゾール－５－イル基などのイミダゾリル基；　ピラゾール－１－イル基、ピラゾール－３－イル基、ピラゾール－４－イル基、ピラゾール－５－イル基などのピラゾリル基；オキサゾール－２－イル基、オキサゾール－４－イル基、オキサゾール－５－イル基などのオキサゾリル基；　イソオキサゾール－３－イル基、イソオキサゾール－４－イル基、イソオキサゾール－５－イル基などのイソオキサゾリル基；　チアゾール－２－イル基、チアゾール－４－イル基、チアゾール－５－イル基などのチアゾリル基；　イソチアゾール－３－イル基、イソチアゾール－４－イル基、イソチアゾール－５－イル基などのイソチアゾリル基；　１，２，３－トリアゾール－１－イル基、１，２，３－トリアゾール－４－イル基、１，２，３－トリアゾール－５－イル基、１，２，４－トリアゾール－１－イル基、１，２，４－トリアゾール－３－イル基、１，２，４－トリアゾール－５－イル基などのトリアゾリル基；　１，２，４－オキサジアゾール－３－イル基、１，２，４－オキサジアゾール－５－イル基、１，３，４－オキサジアゾール－２－イル基などのオキサジアゾリル基；　１，２，４－チアジアゾール－３－イル基、１，２，４－チアジアゾール－５－イル基、１，３，４－チアジアゾール－２－イル基などのチアジアゾリル基；　テトラゾール－１－イル基、テトラゾール－２－イル基などのテトラゾリル基；などが挙げられる。 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, isoxazol-5-yl Isoxazolyl groups such as: thiazolyl groups such as thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group; isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5 -An isothiazolyl group such as an yl group; 1,2,3-triazol-1-yl group, 1,2,3-triazol-4-yl group, 1,2,3-triazol-5-yl group, 1,2 , 4-triazol-1-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-yl group and the like; 1,2,4-oxadiazole- Oxadiazolyl groups such as 3-yl group, 1,2,4-oxadiazol-5-yl group, 1,3,4-oxadiazol-2-yl group; Groups, thiadiazolyl groups such as 1,2,4-thiadiazol-5-yl group and 1,3,4-thiadiazol-2-yl group; tetrazolyl groups such as tetrazol-1-yl group and tetrazol-2-yl group; Etc.
　６員ヘテロアリール基としては、　ピリジン－２－イル基、ピリジン－３－イル基、ピリジン－４－イル基などのピリジル基；　ピラジン－２－イル基、ピラジン－３－イル基などのピラジニル基；　ピリミジン－２－イル基、ピリミジン－４－イル基、ピリミジン－５－イル基などのピリミジニル基；　ピリダジン－３－イル基、ピリダジン－４－イル基などのピリダジニル基；トリアジニル基；などが挙げられる。 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.
　部分不飽和の５員ヘテロ環基としては、２－ピロリン－３－イル基などのピロリニル基；　２－イミダゾリン－１－イル基、２－イミダゾリン－２－イル基、２－イミダゾリン－４－イル基、２－イミダゾリン－５－イル基などのイミダゾリニル基（ジヒドロイミダゾリニル基）；３－ピラゾリン－１－イル基、３－ピラゾリン－２－イル基、３－ピラゾリン－３－イル基、３－ピラゾリン－４－イル基、３－ピラゾリン－５－イル基などのピラゾリニル基；　２－オキサゾリン－２－イル基、２－オキサゾリン－４－イル、２－オキサゾリン－５－イルなどのオキサゾリニル基；　２－イソオキサゾリン－３－イル基、２－イソオキサゾリン－４－イル基、２－イソオキサゾリン－５－イル基、イソオキサゾリン－３－イル基などのイソオキサゾリニル；　２－チアゾリン－２－イル基、２－チアゾリン－４－イル基、３－チアゾリン－２－イル基などのチアゾリニル基；などが挙げられる。 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-5-yl group, and isoxazolin-3-yl group; Kisazoriniru; like; 2-thiazoline-2-yl group, 2-thiazoline-4-yl group, 3-thiazoline-2-yl group thiazolinyl such.
　部分不飽和の６員ヘテロ環基としては、２Ｈ－ピラン－３－イル基などのピラニル基；２Ｈ－チオピラン－３－イル基などのチオピラニル基；２Ｈ－ピリジン－１－イル基、４Ｈ－ピリジン－１－イル基；などが挙げられる。 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.
　飽和５員へテロ環基としては、ピロリジン－１－イル基、ピロリジン－２－イル基、ピロリジン－３－イル基などのピロリジニル基；テトラヒドロフラン－２－イル基、テトラヒドロフラン－３－イル基などのテトラヒドロフラニル基；［１，３］ジオキシラン－２－イル基などのジオキソラニル基；などが挙げられる。
　飽和６員へテロ環基としては、ピペリジン－１－イル基、ピペリジン－２－イル基、ピペリジン－３－イル基、ピペリジン－４－イル基などのピペリジニル基；ピペラジン－１－イル基、ピペラジン－２－イル基などのピペラジニル基；モルホリン－２－イル基、モルホリン－３－イル基、モルホリン－４－イル基などのモルホリニル基などが挙げられる。 Examples of 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. A tetrahydrofuranyl group; a dioxolanyl group such as a [1,3] dioxiran-2-yl group; and the like.
Examples of the saturated 6-membered heterocyclic group 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としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、トリアゾリル基、オキサジアゾリル基、ピリジル基、イソオキサゾリニル基、ピロリジニル基、又はジオキソラニル基であることがより好ましい。 Cy includes pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, oxadiazolyl, pyridyl, isoxazolinyl, pyrrolidinyl, or dioxolanyl. More preferably.
　Ｃｙ上の置換基としては、上記の「置換基」として例示したものと同じものが挙げられる。好ましくは、ハロゲノ基、Ｃ１～６アルキル基、Ｃ３～６シクロアルキル基、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ１～６アルコキシ基、Ｃ６～１０アリール基、Ｃ６～１０アリールオキシ基、Ｃ７～１１アラルキル基、Ｃ７～１１アラルキルオキシ基、Ｃ１～７アシル基、Ｃ１～７アシルオキシ基、Ｃ１～６アルコキシカルボニル基、カルボキシル基、水酸基、オキソ基（＝Ｏ）、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、Ｃ１～７ハロアシル基、シアノ基、ニトロ基、アミノ基、Ｃ１～６アルキルアミノ基、Ｃ１～７アシルアミノ基、Ｃ１～６アルコキシカルボニルアミノ基、カルバモイル基、置換カルバモイル基、メルカプト基、Ｃ１～６アルキルチオ基、Ｃ１～６アルキルスルホニル基、Ｃ６～１０アリールスルホニル基、５員ヘテロアリール基、６員ヘテロアリール基、飽和ヘテロ環基、およびトリＣ１～６アルキルシリル基などを挙げることができる。これらの中でも、ハロゲノ基、Ｃ１～６アルキル基、および水酸基の中から選択された置換基が好ましい。 Examples of the substituent on Cy include the same as those exemplified as the “substituent” above. Preferably, a halogeno group, a C1-6 alkyl group, a C3-6 cycloalkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, a C6-10 aryl group, a C6-10 aryloxy group, C7-11 aralkyl group, C7-11 aralkyloxy group, C1-7 acyl group, C1-7 acyloxy group, C1-6 alkoxycarbonyl group, carboxyl group, hydroxyl group, oxo group (═O), C1-6 haloalkyl group, C1-6 haloalkoxy group, C1-7 haloacyl group, cyano group, nitro group, amino group, C1-6 alkylamino group, C1-7 acylamino group, C1-6 alkoxycarbonylamino group, carbamoyl group, substituted carbamoyl group, Mercapto group, C1-6 alkylthio group, C1-6 alkylsulfonyl group, C6-10 aryl Sulfonyl group, 5-membered heteroaryl group, may be mentioned 6-membered heteroaryl group, a saturated heterocyclic group, and tri-C1 ~ 6 alkyl silyl group and the like. Among these, a substituent selected from a halogeno group, a C1-6 alkyl group, and a hydroxyl group is preferable.
　オキソ基（＝Ｏ）を有する５～６員ヘテロ環基としては、２－オキソ－ピロリジン－１－イル、２－オキソ－ピペリジン－１－イル、２－オキソ－２Ｈ－ピリジン－１－イルなどが挙げられる。これらの中でも、２－オキソ－ピロリジン－１－イルが好ましい。 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が５～６員ヘテロ環基である場合、Ｃｙ上の置換基が隣接して存在する場合が、一緒になって、無置換の若しくは置換基を有する５～８員環を形成してもよい。
　一緒になって形成し得る５～８員環としては、ベンゼン環などの芳香族炭化水素環；　シクロペンテン環、シクロペンタジエン環、シクロヘキセン環、シクロヘプテン環、シクロオクテン環などのＣ５～８シクロアルケン環；などが挙げられる。 When 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. Good.
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は、炭素原子または窒素原子を示す。すなわち、「Ｄ」が縮合してなるピリジン環または「Ｄ」が縮合してなるピラジン環を構成する。
　Ｄは、ピリジン環又はピラジン環を構成する環の一部であり、５～７員炭化水素環または５～７員ヘテロ環を示す。
　５～７員炭化水素環としては、ベンゼン環などの芳香族炭化水素環；　シクロペンテン環、シクロヘキセン環、シクロヘプテン環などのシクロアルケン環；　シクロペンタン環、シクロヘキサン環、シクロヘプタン環などのシクロアルカン環などが挙げられる。
　また、５～７員のヘテロ環としては、フラン環、チオフェン環、ピロ－ル環、イミダゾール環、ピラゾール環、チアゾール環、オキサゾール環、イソオキサゾール環、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、アゼピン環、ジアゼピン環；　ジヒドロ－２Ｈ－ピラン環、ジヒドロ－２Ｈ－チオピラン環、テトラヒドロピリジン環；　ヘキサメチレンイミン環、２－ケトヘキサメチレンイミン環、ホモピペラジン環などが挙げられる。
　式（１）中、Ｄとしては、芳香族炭化水素環が好ましく、ベンゼン環がより好ましい。具体的には、化合物（１）は、キノリン環若しくはキノキサリン環を有する化合物であることが好ましい。 [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.
Examples of 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.
In Formula (1), as D, an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable. Specifically, the compound (1) is preferably a compound having a quinoline ring or a quinoxaline ring.
〔Ｘ１〕
　Ｘ１は、Ｄ、および／または、ピリジン環もしくはピラジン環の置換基であり、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有する５～６員ヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。ｍは、Ｘ１の個数を示し、０～６のいずれかの整数（好ましくは０～２の整数）である。 [X 1 ]
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, unsubstituted It represents a substituted or substituted hydroxyl group, an unsubstituted or substituted amino group, an unsubstituted or substituted mercapto group, a substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group. m represents the number of X 1 and is an integer from 0 to 6 (preferably an integer from 0 to 2).
　Ｘ１における、「Ｃ１～８アルキル基」は、炭素原子１～８個で構成される飽和炭化水素基である。Ｃ１～８アルキル基は直鎖であってもよいし、分岐鎖であってもよい。Ｃ１～８アルキル基としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｎ－ヘプチル基、ｎ－オクチル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、２，２－ジメチルプロピル基、ｉ－ヘキシル基などが挙げられる。これらのうち、Ｃ１～６アルキル基が好ましい。 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. Of these, C1-6 alkyl groups are preferred.
　「置換基を有するＣ１～８アルキル基」としては、シクロプロピルメチル基、２－シクロプロピルエチル基、シクロペンチルメチル基、２－シクロヘキシルエチル基などのシクロアルキルアルキル基、好ましくはＣ３～６シクロアルキルＣ１～６アルキル基；　シクロペンテニルメチル基、３－シクロペンテニルメチル基、３－シクロヘキセニルメチル基、２－（３－シクロヘキセニル）エチル基などのシクロアルケニルアルキル基、好ましくはＣ４～６シクロアルケニルＣ１～６アルキル基；　フルオロメチル基、クロロメチル基、ブロモメチル基、ジフルオロメチル基、ジクロロメチル基、ジブロモメチル基、トリフルオロメチル基、トリクロロメチル基、トリブロモメチル基、２，２，２－トルフルオロエチル基、２，２，２－トリクロロエチル基、ペンタフルオロエチル基、４－フルオロブチル基、４－クロロブチル基、３，３，３－トリフルオロプロピル基、２，２，２－トリフルオロ－１－トリフルオロメチルエチル基、パーフルオロヘキシル基、パークロロヘキシル基、パーフルオロオクチル基、パークロロオクチル基、２，４，６－トリクロロヘキシル基、パーフルオロデシル基、２，２，４，４，６，６－へキサクロロオクチル基などのハロアルキル基、好ましくはＣ１～６ハロアルキル基；　ベンジル基、フェネチル基、３－フェニルプロピル基、１－ナフチルメチル基、２－ナフチルメチル基などのアリールアルキル基（アラルキル基）、好ましくはＣ６～１０アリールＣ１～６アルキル基； 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. ~ 6 alkyl group; 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, perfluorooctyl group, perchlorooctyl group, 2,4,6-trichlorohexyl group, perfluorodecyl group, 2,2,4,4,6,6-hexachlorooctyl group, etc. 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－ピリジルメチル基、３－ピリジルメチル基、４－ピリジルメチル基、２－（２－ピリジル）エチル基、２－（３－ピリジル）エチル基、２－（４－ピリジル）エチル基、３－（２－ピリジル）プロピル基、３－（３－ピリジル）プロピル基、３－（４－ピリジル）プロピル基、２－ピラジニルメチル基、３－ピラジニルメチル基、２－（２－ピラジニル）エチル基、２－（３－ピラジニル）エチル基、３－（２－ピラジニル）プロピル基、３－（３－ピラジニル）プロピル基、２－ピリミジルメチル基、４－ピリミジルメチル基、２－（２－ピリミジル）エチル基、２－（４－ピリミジル）エチル基、３－（２－ピリミジル）プロピル基、３－（４－ピリミジル）プロピル基、２－フリルメチル基、３－フリルメチル基、２－（２－フリル）エチル基、２－（３－フリル）エチル基、３－（２－フリル）プロピル基、３－（３－フリル）プロピル基などのヘテロアリールアルキル基、好ましくは５～６員ヘテロアリールＣ１～６アルキル基；　ヒドロキシメチル基、１－ヒドロキシエチル基、２―ヒドロキシエチル基、１－ヒドロキシプロピル基、３－ヒドロキシプロピル基、１－ヒドロキシ－１－メチルエチル基、２－ヒドロキシ－１，１－ジメチルエチル基、２－ヒドロキシ－１，１－ジメチルプロピル基、２－ヒドロキシ－２－メチルプロピル基などのヒドロキシアルキル基、好ましくはヒドロキシＣ１～６アルキル基； 2-pyridylmethyl group, 3-pyridylmethyl group, 4-pyridylmethyl group, 2- (2-pyridyl) ethyl group, 2- (3-pyridyl) ethyl group, 2- (4-pyridyl) ethyl group, 3- (2-pyridyl) propyl group, 3- (3-pyridyl) propyl group, 3- (4-pyridyl) propyl group, 2-pyrazinylmethyl group, 3-pyrazinylmethyl group, 2- (2-pyrazinyl) ethyl group, 2- (3-pyrazinyl) ethyl group, 3- (2-pyrazinyl) propyl group, 3- (3-pyrazinyl) propyl group, 2-pyrimidylmethyl group, 4-pyrimidylmethyl group, 2- (2-pyrimidyl) ethyl group, 2- (4-pyrimidyl) ethyl group, 3- (2-pyrimidyl) propyl group, 3- (4-pyrimidyl) propyl group, 2-furylmethyl group, 3-furylmethyl group, 2- (2-furyl E) heteroarylalkyl groups such as ethyl, 2- (3-furyl) ethyl, 3- (2-furyl) propyl and 3- (3-furyl) propyl, preferably 5-6 membered heteroaryl C1 ~ 6 alkyl group; hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1,1 A hydroxyalkyl group such as a dimethylethyl group, 2-hydroxy-1,1-dimethylpropyl group, 2-hydroxy-2-methylpropyl group, preferably a hydroxy C1-6 alkyl group;
　メトキシメチル基、エトキシメチル基、２－メトキシエチル基、２－エトキシエチル基、メトキシｎ－プロピル基、ｎ－プロポキシメチル基、ｉ－プロポキシエチル基、ｓ－ブトキシメチル基、ｔ－ブトキシエチル基、２，２－ジメトキシエチル基、２，２－ジメトキシ－１，１－ジメチルエチル基などのアルコキシアルキル基、好ましくはＣ１～６アルコキシＣ１～６アルキル基；　ホルミルオキシメチル基、アセトキシメチル基、２－アセトキシエチル基、プロピオニルオキシメチル基、プロピオニルオキシエチル基などのアシルオキシアルキル基、好ましくはＣ１～７アシルオキシＣ１～６アルキル基；　トリメチルシリルオキシメチル基、ｔ－ブチルジメチルシリルオキシメチル基などのトリアルキルシリルオキシアルキル基、好ましくはトリＣ１～６アルキルシリルオキシＣ１～６アルキル基；　トシルオキシメチル基、２－トシルオキシ－１，１－ジメチルエチル基などのアリールスルホニルオキシアルキル基、好ましくはＣ１～６アルキル置換Ｃ６～１０アリールスルホニルオキシＣ１～６アルキル基；　シアノメチル基、２－シアノエチル基、１－シアノ－１－メチルエチル基などのシアノアルキル基、好ましくはシアノＣ１～６アルキル基；　ホルミルメチル基、２－ホルミルエチル基、３－ホルミルプロピル基、１－ホルミル－１－メチルエチル基、２－ホルミル－１，１－ジメチルエチル基、アセチルメチル基、２－アセチルエチル基、３－アセチルプロピル基、１－アセチル－１－メチルエチル基、２－アセチル－１，１－ジメチルエチル基などのアシルアルキル基、好ましくはＣ１～６アシルＣ１～６アルキル基； Methoxymethyl group, ethoxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, methoxy n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group, Alkoxyalkyl groups such as 2,2-dimethoxyethyl group, 2,2-dimethoxy-1,1-dimethylethyl group, preferably C1-6 alkoxyC1-6 alkyl groups; formyloxymethyl group, acetoxymethyl group, 2- Acyloxyalkyl groups such as acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group, preferably C1-7 acyloxy C1-6 alkyl group; trialkylsilyloxy such as trimethylsilyloxymethyl group, t-butyldimethylsilyloxymethyl group Alkyl group, preferred Or a tri-C1-6 alkylsilyloxy C1-6 alkyl group; an arylsulfonyloxyalkyl group such as a tosyloxymethyl group, 2-tosyloxy-1,1-dimethylethyl group, preferably a C1-6 alkyl substituted C6-10 aryl Sulfonyloxy C1-6 alkyl group; cyanoalkyl group such as cyanomethyl group, 2-cyanoethyl group, 1-cyano-1-methylethyl group, preferably cyanoC1-6 alkyl group; formylmethyl group, 2-formylethyl group, 3-formylpropyl group, 1-formyl-1-methylethyl group, 2-formyl-1,1-dimethylethyl group, acetylmethyl group, 2-acetylethyl group, 3-acetylpropyl group, 1-acetyl-1- Such as methylethyl group, 2-acetyl-1,1-dimethylethyl group Alkyl groups, preferably C1 ~ 6 acyl C1 ~ 6 alkyl group;
　２－ヒドロキシイミノエチル基、２－ヒドロキシイミノ－１－メチルエチル基、２－ヒドロキシ－１，１－ジメチルエチル基、２－ヒドロキシイミノプロピル基などの２－ヒドロキシイミノアルキル基、好ましくは２－ヒドロキシイミノＣ２～６アルキル基；　アセチルメチル基、２－アセチルエチル基、３－アセチルプロピル基、１－アセチル－１－メチルエチル基、２－アセチル－１，１－ジメチルエチル基などのアシルアルキル基、好ましくはホルミルＣ１～６アルキル基；　カルボキシメチル基、２－カルボキシエチル基、３－カルボキシプロピル基、１－カルボキシ－１－メチルエチル基、２－カルボキシ－１，１－ジメチルエチル基などのカルボキシアルキル基、好ましくはカルボキシＣ１～６アルキル基；　メトキシカルボニルメチル基、２－メトキシカルボニルエチル基、３－メトキシカルボニルプロピル基、１－メトキシカルボニル－１－メチルエチル基、２－メトキシカルボニル－１，１－ジメチルエチル基などのアルコキシカルボニルアルキル基、好ましくはＣ１～６アルコキシカルボニルＣ１～６アルキル基；　アジドメチル基、２－アジドエチル基、１－アジド－１－メチルエチル基などのアジドアルキル基、好ましくはアジドＣ１～６アルキル基；などが挙げられる。 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 as a rumethyl group, 2-methoxycarbonylethyl group, 3-methoxycarbonylpropyl group, 1-methoxycarbonyl-1-methylethyl group, 2-methoxycarbonyl-1,1-dimethylethyl group, preferably C1 -6 alkoxycarbonyl C1-6 alkyl group; azidoalkyl groups such as azidomethyl group, 2-azidoethyl group, 1-azido-1-methylethyl group, preferably azido C1-6 alkyl group;
　Ｘ１における、「Ｃ２～８アルケニル基」は、少なくとも１つ炭素－炭素二重結合を有する炭素原子２～８個で構成される不飽和炭化水素基である。Ｃ２～８アルケニル基は直鎖であってもよいし、分岐鎖であってもよい。Ｃ２～８アルケニル基としては、ビニル基、１－プロペニル基、イソプロペニル基、アリル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基、１－ヘプテニル基、６－ヘプテニル基、１－オクテニル基、７－オクテニル基、１－メチル－アリル基、２－メチル－アリル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基などが挙げられる。これらのうち、Ｃ２～６アルケニル基が好ましい。 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 alkenyl groups are preferred.
　「置換基を有するＣ２～８アルケニル基」としては、３－クロロ－２－プロペニル基、４－クロロ－２－ブテニル基、４，４－ジクロロ－３－ブテニル基、４，４－ジフルオロ－３－ブテニル基、３，３－ジクロロ－２－プロペニル基、２，３－ジクロロ－２－プロペニル基、３，３－ジフルオロ－２－プロペニル基、２，４，６－トリクロロ－２－ヘキセニル基などのハロアルケニル基、好ましくはＣ２～６ハロアルケニル基；　３－ヒドロキシ－１－プロペニル基、４－ヒドロキシ－１－ブテニル基、１－ヒドロキシアリル基、１－ヒドロキシ－２－メチルアリル基などのヒドロキシアルケニル基、好ましくはヒドロキシＣ２～６アルケニル基；などが挙げられる。 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.
　Ｘ１における、「Ｃ２～８アルキニル基」は、少なくとも１つ炭素－炭素三重結合を有する炭素原子２～８個で構成される不飽和炭化水素基である。Ｃ２～８アルキニル基は直鎖であってもよいし、分岐鎖であってもよい。Ｃ２～８アルキニル基としては、エチニル基、１－プロピニル基、プロパルギル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－ヘキシニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１，１－ジメチル－２－ブチニル基などが挙げられる。これらのうち、Ｃ２～６アルキニル基が好ましい。 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. Of these, C2-6 alkynyl groups are preferred.
　「置換基を有するＣ２～８アルキニル基」としては、３－クロロ－１－プロピニル基、３－クロロ－１－ブチニル基、３－ブロモ－１－ブチニル基、３－ブロモ－２－プロピニル基、３－ヨード－２－プロピニル基、３－ブロモ－１－ヘキシニル基、４，４，６，６－テトラフルオロ－１－ドデシニル基、５，５－ジクロロ－２－メチル－３－ペンチニル基、４－クロロ－１，１－ジメチル－２－ブチニル基などのハロアルキニル基、好ましくはＣ２～６ハロアルキニル基などが挙げられる。 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.
　Ｘ１における、「Ｃ３～８シクロアルキル基」は、環状部分を有する炭素原子３～８個で構成されるアルキル基である。Ｃ３～８シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基などが挙げられる。これらのうち、Ｃ３～６シクロアルキル基が好ましい。 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.
　「置換基を有するＣ３～８シクロアルキル基」としては、２，３，３－トリメチルシクロブチル基、４，４，６，６－テトラメチルシクロヘキシル基、１，３－ジブチルシクロヘキシル基などのアルキル置換シクロアルキル基、好ましくはＣ１～６アルキル基が１～３個置換したＣ３～６シクロアルキル基などが挙げられる。 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.
　Ｘ１における、「Ｃ４～８シクロアルケニル基」は、環状部分を有する炭素原子４～８個で構成されるアルケニル基である。Ｃ４～８シクロアルケニル基としては、１－シクロブテニル基、１－シクロペンテニル基、３－シクロペンテニル基、１－シクロヘキセニル基、３－シクロヘキセニル基、３－シクロヘプテニル基、４－シクロオクテニル基などが挙げられる。 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.
　「置換基を有するＣ４～８シクロアルケニル基」としては、２－メチル－３－シクロヘキセニル基、３，４－ジメチル－３－シクロヘキセニル基などのアルキル置換シクロアルケニル基、好ましくはＣ１～６アルキル基が１～３個置換したＣ４～６シクロアルケニル基などが挙げられる。 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.
　Ｘ１における、「Ｃ６～１０アリール基」は、単環または多環の炭素数６～１０のアリール基である。なお、多環アリール基は、少なくとも一つの環が芳香環であれば、残りの環が飽和脂環、不飽和脂環または芳香環のいずれであってもよい。Ｃ６～１０アリール基としては、フェニル基、ナフチル基、アズレニル基、インデニル基、インダニル基、テトラリニル基などが挙げられる。これらのうち、フェニル基が好ましい。 The “C6-10 aryl group” in X 1 is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms. In 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. Examples of 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.
　「置換基を有するＣ６～１０アリール基」としては、２－クロロフェニル基、３，５－ジクロロフェニル基、４－フルオロフェニル基、３，５－ジフルオロフェニル基、４－トリフルオロメチルフェニル基、２－メトキシ－１－ナフチル基などの、アルキル置換アリール基、ハロゲノ置換アリール基、アルコキシ置換アリール基、好ましくはＣ１～６アルキル置換Ｃ６～１０アリール基、ハロゲノ置換Ｃ６～１０アリール基、Ｃ１～６アルコキシ置換アリール基が挙げられる。 Examples of the “substituted C6-10 aryl group” 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.
　Ｘ１における、「５～６員ヘテロ環基」は、Ｃｙで例示したものと同じものが挙げられる。 Examples of the “5- to 6-membered heterocyclic group” in X 1 include the same as those exemplified for Cy.
　Ｘ１における、「Ｃ１～８アシル基」は、カルボニル基に、水素原子、Ｃ１～７アルキル基、Ｃ２～７アルケニル基、Ｃ２～７アルキニル基、Ｃ６～７アリール基または５～７員ヘテロ環基が結合した基である。
　Ｃ１～８アシル基としては、ホルミル基；　アセチル基、プロピオニル基、ｎ－プロピルカルボニル基、ｎ－ブチルカルボニル基、ペンタノイル基、バレリル基、オクタノイル基、ｉ－プロピルカルボニル基、ｉ－ブチルカルボニル基、ピバロイル基、イソバレリル基などのアルキルカルボニル基、好ましくはＣ１～６アルキルカルボニル基；　アクリロイル基、メタクリロイル基などのアルケニルカルボニル基、好ましくはＣ２～６アルケニルカルボニル基；　プロピオロイル基などのアルキニルカルボニル基、好ましくはＣ２～６アルキニルカルボニル基；　ベンゾイル基などのアリールカルボニル基；２－ピリジルカルボニル基、チエニルカルボニル基などのヘテロ環カルボニル基などが挙げられる。 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 thienylcarbonyl groups.
　「置換基を有するＣ１～８アシル基」としては、モノフルオロアセチル基、モノクロロアセチル基、モノブロモアセチル基、ジフルオロアセチル基、ジクロロアセチル基、ジブロモアセチル基、トリフルオロアセチル基、トリクロロアセチル基、トリブロモアセチル基、３，３，３－トリフルオロプロピオニル基、３，３，３－トリクロロプロピオニル基、２，２，３，３，３－ペンタフルオロプロピオニル基などのハロアシル基、好ましくはＣ１～７ハロアシル基などが挙げられる。 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.
　Ｘ１における、「（１－イミノ）Ｃ１～８アルキル基」は、イミノメチル基、若しくはイミノメチル基にＣ１～７のアルキル基が結合した基である。（１－イミノ）Ｃ１～８アルキル基としては、イミノメチル基、（１－イミノ）エチル基、（１－イミノ）プロピル基、（１－イミノ）ブチル基、（１－イミノ）ペンチル基、（１－イミノ）ヘキシル基、（１－イミノ）ヘプチル基などが挙げられる。これらのうち、（１－イミノ）Ｃ１～６アルキル基が好ましい。 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.
　「置換基を有する（１－イミノ）アルキル基」としては、ヒドロキシイミノメチル基、（１－ヒドロキシイミノ）エチル基、（１－ヒドロキシイミノ）プロピル基、（１－ヒドロキシイミノ）ブチル基などの（１－ヒドロキシイミノ）Ｃ１～８アルキル基；好ましくは（１－ヒドロキシイミノ）Ｃ１～６アルキル基；　メトキシイミノメチル基、（１－エトキシイミノ）メチル基、（１－メトキシイミノ）エチル基、（１－ｔ－ブトキシイミノ）エチル基、（１－エトキシイミノ）エチル基などの（１－アルコキシイミノ）Ｃ１～８アルキル基、好ましくは（１－（Ｃ１～６アルコキシ）イミノ）Ｃ１～６アルキル基；などが挙げられる。 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.
　Ｘ１における、「置換基を有するカルボキシル基」は、カルボニル基に、Ｃ１～６アルキル基、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ６～１０アリール基、Ｃ６～１０アリールＣ１～６アルキル基または５～６員ヘテロ環基が結合した基である。
　「置換基を有するカルボキシル基」としては、メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｉ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基、ｎ－ペンチルオキシカルボニル基、ｎ－ヘキシルオキシカルボニル基などのアルコキシカルボニル基、好ましくはＣ１～６アルコキシカルボニル基；　ビニルオキシカルボニル基、アリルオキシカルボニル基などのアルケニルオキシカルボニル基、好ましくはＣ２～６アルケニルオキシカルボニル基；　エチニルオキシカルボニル基、プロパルギルオキシカルボニル基などのアルキニルオキシカルボニル基、好ましくはＣ２～６アルキニルオキシカルボニル基；　フェノキシカルボニル基、ナフトキシカルボニル基などのアリールオキシカルボニル基、好ましくはＣ６～１０アリールオキシカルボニル基；　ベンジルオキシカルボニル基などのアラルキルオキシカルボニル基、好ましくはＣ６～１０アリールＣ１～６アルコキシカルボニル基；などが挙げられる。 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 group Aryloxycarbonyl groups such as carbonyl groups, preferably C6 ~ 10 aryloxycarbonyl group; aralkyloxycarbonyl groups such as benzyloxycarbonyl group, preferably C6 ~ 10 aryl C1 ~ 6 alkoxycarbonyl group; and the like.
　Ｘ１における、「置換基を有するカルバモイル基」は、カルバモイル基に、Ｃ１～６アルキル基、Ｃ２～６アルケニル基、Ｃ２～６アルキニル基、Ｃ６～１０アリール基、Ｃ６～１０アリールＣ１～６アルキル基、または５～６員ヘテロ環基が結合した基である。「置換基を有するカルバモイル基」としては、メチルカルバモイル基、エチルカルバモイル基、ジメチルカルバモイル基、ジエチルカルバモイル基などのモノアルキルカルバモイル基またはジアルキルカルバモイル基、好ましくはモノＣ１～６アルキルカルバモイル基またはジＣ１～６アルキルカルバモイル基；　フェニルカルバモイル基、４－メチルフェニルカルバモイル基などのモノアリールカルバモイル基、好ましくはモノＣ６～１０アリールカルバモイル基；などが挙げられる。 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. As the “carbamoyl group having a substituent”, 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.
　Ｘ１における、「置換基を有する水酸基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、デシルオキシ基、ドデシルオキシ基、ラウリルオキシ基、ｉ－プロポキシ基、ｉ－ブトキシ基、ｓ－ブトキシ基、ｔ－ブトキシ基、１－エチルプロポキシ基、ｉ－ヘキシルオキシ基、４－メチルペントキシ基、３－メチルペントキシ基、２－メチルペントキシ基、１－メチルペントキシ基、３，３－ジメチルブトキシ基、２，２－ジメチルブトキシ基、１，１－ジメチルブトキシ基、１，２－ジメチルブトキシ基、１，３－ジメチルブトキシ基、２，３－ジメチルブトキシ基、１－エチルブトキシ基、２－エチルブトキシ基などのアルコキシ基、好ましくはＣ１～６アルコキシ基； 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. Oxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, 1-ethylpropoxy group, i-hexyloxy group, 4-methylpentoxy group, 3-methylpentoxy group, 2 -Methylpentoxy group, 1-methylpentoxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3-dimethyl Alkoxy groups such as butoxy group, 2,3-dimethylbutoxy group, 1-ethylbutoxy group, 2-ethylbutoxy group, preferably C1-6 alkoxy Si group;
　シクロプロピルメチルオキシ基、２－シクロペンチルエチルオキシ基などのシクロアルキルアルコキシ基、好ましくはＣ３～８シクロアルキルＣ１～６アルコキシ基；　ベンジルオキシ基などのアラルキルオキシ基、好ましくはＣ６～１０アリールＣ１～６アルコキシ基；　クロロメトキシ基、ジクロロメトキシ基、トリクロロメトキシ基、トリフルオロメトキシ基、１－フルオロエトキシ基、１，１－ジフルオロエトキシ基、２，２，２－トリフルオロエトキシ基、ペンタフルオロエトキシ基などのハロアルコキシ基、好ましくはＣ１～６ハロアルコキシ基；　ビニルオキシ基、１－プロペニルオキシ基、アリルオキシ基、１－ブテニルオキシ基、２－ブテニルオキシ基、３－ブテニルオキシ基、１－ペンテニルオキシ基、２－ペンテニルオキシ基、３－ペンテニルオキシ基、４－ペンテニルオキシ基、１－ヘキセニルオキシ基、２－ヘキセニルオキシ基、３－ヘキセニルオキシ基、４－ヘキセニルオキシ基、５－ヘキセニルオキシ基、１－メチル－２－プロペニルオキシ基、２－メチル－２－プロペニルオキシ基、１－メチル－２－ブテニルオキシ基、２－メチル－２－ブテニルオキシ基などのアルケニルオキシ基、好ましくはＣ２～６アルケニルオキシ基； 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;
　エチニルオキシ基、プロピニルオキシ基、プロパルギルオキシ基、１－ブチニルオキシ基、２－ブチニルオキシ基、３－ブチニルオキシ基、１－ペンチニルオキシ基、２－ペンチニルオキシ基、３－ペンチニルオキシ基、４－ペンチニルオキシ基、１－ヘキシニルオキシ基、１－メチル－２－プロピニルオキシ基、２－メチル－３－ブチニルオキシ基、１－メチル－２－ブチニルオキシ基、２－メチル－３－ペンチニルオキシ基、１，１－ジメチル－２－ブチニルオキシ基などのアルキニルオキシ基、好ましくはＣ２～６アルキニルオキシ基；　シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基、シクロヘプチルオキシ基、シクロオクチルオキシ基、２－メチルシクロプロピルオキシ基、２－エチルシクロプロピルオキシ基、２，３，３－トリメチルシクロブチルオキシ基、２－メチルシクロペンチルオキシ基、２－エチルシクロヘキシルオキシ基、２－エチルシクロオクチルオキシ基、４，４，６，６－テトラメチルシクロヘキシルオキシ基、１，３－ジブチルシクロヘキシルオキシ基などのシクロアルキルオキシ基、好ましくはＣ３～６シクロアルキルオキシ基；　フェニルオキシ基、ナフチルオキシ基、アズレニルオキシ基、インデニルオキシ基、インダニルオキシ基、テトラリニルオキシ基などのアリールオキシ基、好ましくはＣ６～１０アリールオキシ基；　ベンジルオキシ基、フェネチルオキシ基、２－ナフチルメチルオキシ基などのアリールアルキルオキシ基（アラルキルオキシ基）、好ましくはＣ６～１０アリールＣ１～６アルキルオキシ基；　アセチルオキシ基、プロピオニルオキシ基、ｎ－プロピルカルボニルオキシ基、ｉ－プロピルカルボニルオキシ基、ｎ－ブチルカルボニルオキシ基、ｉ－ブチルカルボニルオキシ基、ペンタノイルオキシ基、ピバロイルオキシ基などのアシルオキシ基、好ましくはＣ１～７アシルオキシ基；　メトキシカルボニルメチルオキシ基、１－メトキシカルボニル－１－メチルエチルオキシ基などのアルコキシカルボニルアルキルオキシ基、好ましくはＣ１～６アルコキシカルボニルＣ１～６アルコキシ基；　トリメチルシリルオキシ基、ｔ－ブチルジメチルシリルオキシ基などのトリアルキルシリルオキシ基、好ましくはトリＣ１～６アルキルシリルオキシ基；
などが挙げられる。 Ethynyloxy group, propynyloxy group, propargyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4- Pentynyloxy group, 1-hexynyloxy group, 1-methyl-2-propynyloxy group, 2-methyl-3-butynyloxy group, 1-methyl-2-butynyloxy group, 2-methyl-3-pentynyloxy group, 1 , 1-dimethyl-2-butynyloxy group, preferably C2-6 alkynyloxy group; cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group Group, 2-methylcyclopropyloxy group, 2 -Ethylcyclopropyloxy group, 2,3,3-trimethylcyclobutyloxy group, 2-methylcyclopentyloxy group, 2-ethylcyclohexyloxy group, 2-ethylcyclooctyloxy group, 4,4,6,6-tetra A cycloalkyloxy group such as a methylcyclohexyloxy group or a 1,3-dibutylcyclohexyloxy group, preferably a C3-6 cycloalkyloxy group; a phenyloxy group, a naphthyloxy group, an azulenyloxy group, an indenyloxy group, an indanyloxy group; Aryloxy groups such as tetralinyloxy groups, preferably C6-10 aryloxy groups; arylalkyloxy groups (aralkyloxy groups) such as benzyloxy groups, phenethyloxy groups, 2-naphthylmethyloxy groups, preferably C6 ~ 10 aryl 1-6 alkyloxy groups; acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, pentanoyloxy group, pivaloyloxy group An acyloxy group such as, preferably a C1-7 acyloxy group; an alkoxycarbonylalkyloxy group such as a methoxycarbonylmethyloxy group, 1-methoxycarbonyl-1-methylethyloxy group, preferably a C1-6 alkoxycarbonyl C1-6 alkoxy group A trialkylsilyloxy group such as a trimethylsilyloxy group or t-butyldimethylsilyloxy group, preferably a tri-C1-6 alkylsilyloxy group;
Etc.
　「置換基を有するアミノ基」としては、メチルアミノ基、エチルアミノ基、ｎ－プロピルアミノ基、ｎ－ブチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのアルキルアミノ基、好ましくはモノＣ１～６アルキルアミノ基またはジＣ１～６アルキルアミノ基；　メチリデンアミノ基、エチリデンアミノ基などのモノＣ１～６アルキリデンアミノ基；　フェニルアミノ基、４－メチルフェニルアミノ基などのモノアリールアミノ基、好ましくはモノＣ６～１０アリールアミノ基；　ジ１－ナフチルアミノ基などのジアリールアミノ基、好ましくはジＣ６～１０アリールアミノ基；　ベンジルアミノ基などのアラルキルアミノ基、好ましくはＣ６～１０アリールＣ１～６アルキルアミノ基；　アセチルアミノ基、トリフルオロアセチルアミノ基、ベンゾイルアミノ基などのアシルアミノ基、好ましくはＣ１～６アシルアミノ基；　メトキシカルボニルアミノ基、ｔ－ブトキシカルボニルアミノ基などのアルコキシカルボニルアミノ基、好ましくはＣ１～６アルコキシカルボニルアミノ基；などが挙げられる。 As the “amino group having a substituent”, 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; acetylamino Group, trifluoroacetyl An acylamino group such as a mino group or a benzoylamino group, preferably a C1-6 acylamino group; an alkoxycarbonylamino group such as a methoxycarbonylamino group or a t-butoxycarbonylamino group, preferably a C1-6 alkoxycarbonylamino group; It is done.
　Ｘ１における、「置換基を有するメルカプト基」としては、メチルチオ基、エチルチオ基などのアルキルチオ基、好ましくはＣ１～６アルキルチオ基；　フェニルチオ基、４－メチルフェニルチオ基などのアリールチオ基、好ましくはＣ６～１０アリールチオ基；　アセチルチオ基、ベンゾイルチオ基などのアシルチオ基、好ましくはＣ１～６アシルチオ基；などが挙げられる。 As the “mercapto group having a substituent” in X 1 , 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;
　Ｘ１における、「置換基を有するスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｎ－プロピルスルホニル基、ｉ－プロピルスルホニル基、ｎ－ブチルスルホニル基、ｉ－ブチルスルホニル基、ｓ－ブチルスルホニル基、ｔ－ブチルスルホニル基、ｎ－ペンチルスルホニル基、ｉ－ペンチルスルホニル基、ネオペンチルスルホニル基、１－エチルプロピルスルホニル基、ｎ－ヘキシルスルホニル基、ｉ－ヘキシルスルホニル基などのアルキルスルホニル基、好ましくはＣ１～６アルキルスルホニル基；　トリフルオロメチルスルホニル基などのハロアルキルスルホニル基、好ましくはＣ１～６ハロアルキルスルホニル基；　フェニルスルホニル基、４－メチルフェニルスルホニル基などのアリールスルホニル基、好ましくはＣ６～１０アリールスルホニル基；　スルフォ基；メトキシスルホニル基、エトキシスルホニル基などのアルコキシスルホニル基、好ましくはＣ１～６アルコキシスルホニル基；　スルファモイル基；Ｎ－メチルスルファモイル基、Ｎ－エチルスルファモイル基、Ｎ，Ｎ－ジメチルスルファモイル基、Ｎ，Ｎ－ジエチルスルファモイル基などのスルファモイル基、好ましくはモノＣ１～６アルキルスルファモイル基またはジＣ１～６アルキルスルファモイル基；　フェニルスルファモイル基、４－メチルフェニルスルファモイル基などのモノアリールスルファモイル基、好ましくはモノＣ６～１０アリールスルファモイル基；などが挙げられる。 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; sulfo group; alkoxysulfonyl group such as methoxysulfonyl group and ethoxysulfonyl group, preferably C1-6 alkoxysulfonyl group; sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group A sulfamoyl group such as N, N-dimethylsulfamoyl group, N, N-diethylsulfamoyl group, preferably a mono C1-6 alkylsulfamoyl group or a diC1-6 alkylsulfamoyl group; And a monoarylsulfamoyl group such as a moyl group and 4-methylphenylsulfamoyl group, preferably a mono C6-10 arylsulfamoyl group.
　Ｘ１における、「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などが挙げられる。
　これらの中でも、Ｘ１は、ハロゲノ基又はＣ１～Ｃ８アルキル基であることが好ましい。 Examples of the “halogeno group” in X 1 include a fluoro group, a chloro group, a bromo group, and an iodo group.
Among these, X 1 is preferably a halogeno group or a C1-C8 alkyl group.
〔Ｅ〕
　Ｅは、５～７員炭化水素環または５～７員ヘテロ環を示す。
　５～７員炭化水素環としては、ベンゼン環などの芳香族炭化水素環；　シクロペンテン環、シクロヘキセン環、シクロヘプテン環などのＣ５～７シクロアルケン環；　フラン環、チオフェン環、ピロ－ル環、イミダゾール環、ピラゾール環、チアゾール環、オキサゾール環、イソオキサゾール環、イソチアゾール環、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、アゼピン環、ジアゼピン環などの芳香族５～７員ヘテロ環；などが挙げられる。
　これらのうち芳香族炭化水素環又は芳香族５～６員ヘテロ環が好ましく、ベンゼン環又はピリジン環がより好ましく、ベンゼン環がより更に好ましい。 [E]
E represents a 5- to 7-membered hydrocarbon ring or a 5- to 7-membered heterocyclic ring.
As the 5- to 7-membered hydrocarbon 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; .
Of these, an aromatic hydrocarbon ring or an aromatic 5- to 6-membered hetero ring is preferable, a benzene ring or a pyridine ring is more preferable, and a benzene ring is still more preferable.
〔Ｘ２〕
　Ｘ２は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有する５～６員ヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示す。ｎは、Ｘ２の個数を示し、０～４のいずれかの整数、好ましくは０～２のいずれかの整数、より更に好ましくは０または１である。 [X 2 ]
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 group, an unsubstituted or substituted mercapto group, a substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group is shown. n represents the number of X 2 and is an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 0 or 1.
　Ｘ２における、「Ｃ１～８アルキル基」、「Ｃ２～８アルケニル基」、「Ｃ２～８アルキニル基」、「Ｃ３～８シクロアルキル基」、「Ｃ４～８シクロアルケニル基」、「Ｃ６～１０アリール基」、「５～６員ヘテロ環基」、「Ｃ１～８アシル基」、「（１－イミノ）Ｃ１～８アルキル基」、「置換基を有するカルボキシル基」、「置換基を有するカルバモイル基」、「置換基を有する水酸基」、「置換基を有するアミノ基」、「置換基を有するメルカプト基」、「置換基を有するスルホニル基」、「ハロゲノ基」は、Ｘ１で例示したものと同じものが挙げられる。
　これらの中でも、Ｘ２は、ハロゲノ基又はＣ１～８アルキル基であることが好ましい。 “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.
Among these, X 2 is preferably a halogeno group or a C1-8 alkyl group.
〔Ｘ〕
　Ｘは、酸素原子、硫黄原子、－Ｃ（＝Ｏ）－基で表される基、または－ＣＨＯＨ－基で表される基を示す。これらの中でも、Ｘは、酸素原子又は硫黄原子であることが好ましく、酸素原子であることがより好ましい。 [X]
X represents an oxygen atom, a sulfur atom, a group represented by —C (═O) — group, or a group represented by —CHOH— group. Among these, X is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
〔式（２）で表される化合物〕
　前記化合物（１）は、式（２）で表される化合物（以下、「化合物（２）」と表記することがある。）であることが好ましい。 [Compound represented by Formula (2)]
The compound (1) is preferably a compound represented by the formula (2) (hereinafter sometimes referred to as “compound (2)”).
Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010
　ここで、上記の式（２）中、Ｃｙ、Ｘ１、ｍ、Ｘ２、ｎ、Ｂ、およびＸは、上記の式（１）中のそれぞれと同じ意味を示す。 Here, in the above formula (2), Cy, X 1 , m, X 2, n, B, and X are as defined respectively in the above formula (1).
〔Ａ１、Ａ２、Ａ３、Ａ４〕
　Ａ１、Ａ２、Ａ３、およびＡ４は、それぞれ独立して、炭素原子または窒素原子を示す。すなわち、ベンゼン環、ピリジン環、ピリダジン環、ピリミジン環、ピラジン環、またはトリアジン環を構成する。前記ピリジン環としては、Ａ１が窒素原子であるピリジン環が好ましい。これらの中でも、Ａ１、Ａ２、Ａ３、およびＡ４は、ベンゼン環またはピリジン環を構成することが好ましい。 [A 1, A 2, A 3 , A 4 ]
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. As the pyridine ring, a pyridine ring in which A 1 is a nitrogen atom is preferable. Among these, A 1 , A 2 , A 3 , and A 4 preferably constitute a benzene ring or a pyridine ring.
〔式（３）で表される化合物〕
　前記化合物（１）は、式（３）で表される化合物（以下、「化合物（３）」と表記することがある。）であることが好ましい。 [Compound represented by Formula (3)]
The compound (1) is preferably a compound represented by the formula (3) (hereinafter sometimes referred to as “compound (3)”).
Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011
　ここで、式（３）中、Ｃｙ、Ｘ１、ｍ、Ｘ２、Ｂ、およびＸは、上記の式（１）中のそれぞれと同じ意味を示す。ｎ１は、Ｘ２の個数を示し、０～３のいずれかの整数、好ましくは０～２のいずれかの整数である。 Here, in the formula (3), Cy, X 1 , m, X 2 , B, and X have the same meaning as in the above formula (1). n1 represents the number of X 2 and is an integer of 0 to 3, preferably an integer of 0 to 2.
〔Ａ５、Ａ６、Ａ７〕
　Ａ５、Ａ６、およびＡ７は、それぞれ独立して、炭素原子、窒素原子、酸素原子、または硫黄原子を示す。ただし、酸素原子同士、硫黄原子同士、酸素原子と硫黄原子の組合わせが隣接することはない。
　すなわち、Ａ５、Ａ６、およびＡ７を含む環は、フラン環、チオフェン環、ピロ－ル環、イミダゾール環、ピラゾール環、チアゾール環、オキサゾール環、イソオキサゾール環、イソチアゾール環を構成する。この場合、ピラゾール環としては、Ａ６とＡ７が窒素原子であるピラゾール環が好ましい。チオフェン環としては、Ａ７が硫黄原子であるチオフェン環が好ましい。 [A 5, A 6, A 7]
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.
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. In this case, the pyrazole ring is preferably a pyrazole ring in which A 6 and A 7 are nitrogen atoms. As the thiophene ring, a thiophene ring in which A 7 is a sulfur atom is preferable.
〔式（４）で表される化合物〕
　前記化合物（１）は、式（４）で表される化合物（以下、「化合物（４）」と表記することがある。）であることが好ましい。 [Compound represented by Formula (4)]
The compound (1) is preferably a compound represented by the formula (4) (hereinafter sometimes referred to as “compound (4)”).
Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012
　ここで、上記の式（４）中、Ｃｙ、Ｄ、Ｘ１、ｍ、Ｘ２、およびｎは、上記の式（１）中のそれぞれと同じ意味を示す。
　式（４）中、Ｄとしては、芳香族炭化水素環が好ましく、ベンゼン環がより好ましい。具体的には、化合物（４）は、キノリン環を有する化合物であることが好ましい。 Here, in the above formula (4), Cy, D, X 1, m, X 2, and n have the same meanings as each of the above formulas (1).
In formula (4), as D, an aromatic hydrocarbon ring is preferable, and a benzene ring is more preferable. Specifically, the compound (4) is preferably a compound having a quinoline ring.
　本発明に係る含窒素ヘテロ環化合物の塩若しくはＮ－オキサイド化合物は、農園芸学的に許容される塩若しくはＮ－オキサイド化合物であれば、特に制限されない。塩としては、例えば、塩酸、硫酸などの無機酸の塩；酢酸、乳酸などの有機酸の塩；リチウム、ナトリウム、カリウムなどのアルカリ金属の塩；カルシウム、マグネシウムなどのアルカリ土類金属の塩；鉄、銅などの遷移金属の塩；アンモニア、トリエチルアミン、トリブチルアミン、ピリジン、ヒドラジンなどの有機塩基の塩などが挙げられる。 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. Examples of 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.
〔本発明に係る含窒素ヘテロ環化合物の製造方法〕
　本発明に係る含窒素ヘテロ環化合物は、例えば、以下に示す合成方法によって製造することができる。 [Method for producing nitrogen-containing heterocyclic compound according to the present invention]
The nitrogen-containing heterocyclic compound according to the present invention can be produced, for example, by the synthesis method shown below.
（合成方法１）
　式（Ａ）で表される化合物と式（Ｂ）で表される化合物とを公知の方法によって反応させて化合物（２）を製造することができる。
　式中、Ｘ１、ｍ、Ｘ２、ｎ、Ａ１～Ａ４、Ｂ、およびＸは前記と同じ意味を示す。Ｑはハロゲノ基を示す。
　式中、Ｒは、前記のＣｙに挙げるヘテロ環基またはヘテロ環基に誘導可能な官能基を表す。官能基の例としては、オキサゾール－２－イル基の場合は、ホルミル基（イソニトリル類との縮合により誘導できる。）；イソオキサゾリン－３－イル基の場合は、ヒドロキシイミノ基（オレフィン類との２＋３環化反応により誘導できる。）；鈴木・宮浦カップリングを用いる場合は、ハロゲン原子またはホウ素基；などが挙げられる。
　本発明においては、７，８－ジフルオロ－３－ヨード－キノリンが、有用な製造中間体である。 (Synthesis method 1)
The compound represented by formula (A) and the compound represented by formula (B) can be reacted by a known method to produce compound (2).
In the formula, X 1 , m, X 2 , n, A 1 to A 4 , B, and X have the same meaning as described above. Q represents a halogeno group.
In the formula, R represents a heterocyclic group listed in the above Cy or a functional group derivable to the heterocyclic group. Examples of functional groups include formyl groups (which can be derived by condensation with isonitriles) in the case of oxazol-2-yl groups; hydroxyimino groups (with olefins) in the case of isoxazolin-3-yl groups. In the case of using Suzuki-Miyaura coupling, a halogen atom or a boron group can be used.
In the present invention, 7,8-difluoro-3-iodo-quinoline is a useful production intermediate.
Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013
（合成方法２）
　式（Ｃ）で表される化合物と式（Ｄ）で表される化合物とを公知の方法によって反応させて化合物（２）を製造することができる。
　式中、Ｒ、Ｘ１、ｍ、Ｘ２、ｎ、Ａ１～Ａ４、Ｂ、Ｘ、およびＱは前記と同じ意味を示す。
　本発明においては、８－フルオロ－３－ヒドロキシキノリン、７，８－ジフルオロ－３－ヒドロキシキノリン、８－フルオロ－３－ヒドロキシ－２－メチルキノリン、または７，８－ジフルオロ－３－ヒドロキシ－２－メチルキノリンが、有用な製造中間体である。 (Synthesis method 2)
Compound (2) can be produced by reacting the compound represented by formula (C) with the compound represented by formula (D) by a known method.
In the formula, R, X 1 , m, X 2 , n, A 1 to A 4 , B, X, and Q have the same meaning as described above.
In the present invention, 8-fluoro-3-hydroxyquinoline, 7,8-difluoro-3-hydroxyquinoline, 8-fluoro-3-hydroxy-2-methylquinoline, or 7,8-difluoro-3-hydroxy-2 -Methylquinoline is a useful production intermediate.
Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014
（合成方法３）
　式（Ａ）で表される化合物と式（Ｅ）で表される化合物とを公知の方法によって反応させて化合物（３）を製造することができる。
　式中、Ｒ、Ｘ１、ｍ、Ｘ２、ｎ、Ａ５～Ａ７、Ｂ、Ｘ、およびＱは前記と同じ意味を示す。 (Synthesis method 3)
Compound (3) can be produced by reacting the compound represented by formula (A) with the compound represented by formula (E) by a known method.
In the formula, R, X 1 , m, X 2 , n, A 5 to A 7 , B, X, and Q have the same meaning as described above.
Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015
（合成方法４）
　式（Ｃ）で表される化合物と式（Ｆ）で表される化合物とを公知の方法によって反応させて化合物（３）を製造することができる。
　式中、Ｒ、Ｘ１、ｍ、Ｘ２、ｎ、Ａ５～Ａ７、Ｂ、Ｘ、およびＱは前記と同じ意味を示す。 (Synthesis method 4)
Compound (3) can be produced by reacting the compound represented by formula (C) with the compound represented by formula (F) by a known method.
In the formula, R, X 1 , m, X 2 , n, A 5 to A 7 , B, X, and Q have the same meaning as described above.
Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016
（合成方法５）
　式（Ｇ）で表される化合物と式（Ｈ）で表される化合物とを公知の方法によって反応させて化合物（４）を製造することができる。 (Synthesis method 5)
Compound (4) can be produced by reacting the compound represented by formula (G) with the compound represented by formula (H) by a known method.
Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017
　式中、Ｘ１、Ｘ２、Ｄ、ｍ、ｎ、Ｑ、およびＲは前記と同じ意味を表す。 In the formula, X 1 , X 2 , D, m, n, Q, and R represent the same meaning as described above.
（合成方法６）
　式（Ｊ）で表される化合物と式（Ｋ）で表される化合物とを公知の方法によって反応させて化合物（４）を製造することができる。 (Synthesis method 6)
Compound (4) can be produced by reacting the compound represented by formula (J) with the compound represented by formula (K) by a known method.
Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018
　式中、Ｒ、Ｘ１、Ｘ２、Ｄ、Ｑ、ｍ、およびｎは前記と同じ意味を表す。 In the formula, R, X 1 , X 2 , D, Q, m, and n represent the same meaning as described above.
　本発明に係る化合物の塩は、無機酸化合物、有機酸化合物、アルカリ金属化合物、アルカリ土類金属化合物、遷移金属化合物、アンモニウム化合物などを化合物（１）に接触させることによって調製することができる。
　また、本発明に係るＮ－オキサイド化合物は、既知の酸化反応によって調製することができる。例えば、溶媒中または無溶媒において、化合物（１）と、過酸化水素などの過酸化物とを接触させることによって調製することができる。 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.
　いずれの反応においても、反応終了後は、有機合成化学における通常の後処理操作、および、必要に応じて従来公知の分離精製手段を施すことによって、目的物を効率よく単離することができる。 In any reaction, after completion of the reaction, 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.
　目的物の構造は、１Ｈ－ＮＭＲスペクトル、ＩＲスペクトル、マススペクトルの測定や、元素分析などによって、同定・確認することができる。 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.
２）農園芸用殺菌剤
　本発明に係る農園芸用殺菌剤は、本発明に係る含窒素ヘテロ環化合物またはその塩若しくはＮ－オキサイド化合物から選ばれる少なくとも１種を有効成分として含有するものである。 2) Agricultural and horticultural fungicide 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. .
　本発明の農園芸用殺菌剤は、広範囲の種類の糸状菌、例えば、藻菌類（Oomycetes）、子のう（嚢）菌類（Ascomycetes）、不完全菌類（Deuteromycetes）、担子菌類（Basidiomycetes）に属する菌に対し優れた殺菌力を有する。 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.
　本発明の農園芸用殺菌剤は、花卉、芝、牧草を含む農園芸作物の栽培に際し発生する種々の病害の防除のために、種子処理、茎葉散布、土壌施用または水面施用などの方法において使用することができる。 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.
　例えば、
　テンサイ：褐斑病（Cercospora beticola)、黒根病(Aphanomyces cochlloides)、根腐病(Thanatephorus cucumeris)、葉腐病(Thanatephorus cucumeris)；
　ラッカセイ：褐斑病(Mycosphaerella arachidis)、黒渋病(Mycosphaerella berkeleyi)；
　キュウリ：うどんこ病(Sphaerotheca fuliginea)、べと病(Pseudoperonospora cubensis)、つる枯病(Mycosphaerella melonis)、つる割病(Fusarium oxysporum)、菌核病(Sclerotinia sclerotiorum)、灰色かび病(Botrytis cinerea)、炭そ病(Colletotrichum orbiculare)、黒星病(Cladosporium cucumerinum)、褐斑病(Corynespora cassicola)、苗立枯病(Pythium debaryanam、Rhizoctonia solani Kuhn)、斑点細菌病(Pseudomonas syringae pv.Lecrymans)；
　トマト：灰色かび病(Botrytis cinerea)、葉かび病(Cladosporium fulvum)、疫病(Phytophthora infestans)；
　ナス：灰色かび病(Botrytis cinerea)、黒枯病(Corynespora melongenae)、うどんこ病(Erysiphe cichoracearum)、すすかび病(Mycovellosiella nattrassii)； For example,
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 (Pythium debaryanam, Rhizoctonia solani Kuhn), spot bacterial disease (Pseudomonas syringae pv. Lecrymans);
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);
　イチゴ：灰色かび病(Botrytis cinerea)、うどんこ病(Sohaerotheca humuli)、炭そ病(Colletotrichum acutatum、Colletotrichum fragariae)、疫病(Phytophthora cactorum)；
　タマネギ：灰色腐敗病(Botrytis allii)、灰色かび病(Botrytis cinerea)、白斑葉枯病(Botrytis squamosa)、べと病(Peronospora destructor)；
　キャベツ：根こぶ病(Plasmodiophora brassicae)、軟腐病(Erwinia carotovora)、べと病(Peronospora parasitica)；
　インゲン：菌核病(Sclerotinia sclerotiorum)、灰色かび病(Botrytis cinerea)；
　りんご：うどんこ病(Podosphaera leucotricha)、黒星病(Venturia inaequalis)、モニリア病(Monilinia mali)、黒点病(Mycosphaerella pomi)、腐らん病(Valsa mali)、斑点落葉病(Alternaria mali)、赤星病(Gymnosporangium yamadae)、輪紋病(Botryosphaeria berengeriana)、炭そ病(Glomerella cingulata、Colletotrichum acutatum)、褐斑病(Diplocarpon mali)、すす点病(Zygophiala jamaicensis)、すす斑病(Gloeodes pomigena)；
　カキ：うどんこ病(Phyllactinia kakicola)、炭そ病(Gloeosporium kaki)、角斑落葉病(Cercospora kaki)； Strawberry: Gray mold (Botrytis cinerea), powdery mildew (Sohaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae), plague (Phytophthora cactorum);
Onion: gray rot (Botrytis allii), gray mold (Botrytis cinerea), white leaf blight (Botrytis squamosa), downy mildew (Peronospora destructor);
Cabbage: root-knot disease (Plasmodiophora brassicae), soft rot disease (Erwinia carotovora), downy mildew (Peronospora parasitica);
Green beans: Sclerotinia sclerotiorum, gray mold (Botrytis cinerea);
Apple: powdery mildew (Podosphaera leucotricha), black spot disease (Venturia inaequalis), monilinia disease (Monilinia mali), black spot disease (Mycosphaerella pomi), rot disease (Valsa mali), spotted leaf disease (Alternaria mali), red star disease (Gymnosporang) yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena);
Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), deciduous leaf spot (Cercospora kaki);
　モモ：灰星病(Monilinia fructicola)、黒星病(Cladosporium carpophilum)、ホモプシス腐敗病(Phomopsis sp.)；
　オウトウ：灰星病(Monilinia fructicola)；
　ブドウ：灰色かび病(Botrytis cinerea)、うどんこ病(Uncinula necator)、晩腐病(Glomerella cingulata、Colletotrichum acutatum)、べと病(Plasmopara viticola)、黒とう病(Elsinoe ampelina)、褐斑病(Pseudocercospora vitis)、黒腐病(Guignardia bidwellii)；
　ナシ：黒星病(Venturia nashicola)、赤星病(Gymnosporangium asiaticum)、黒斑病(Alternaria kikuchiana)、輪紋病(Botryosphaeria berengeriana)、うどんこ病(Phyllactinia mali)；
　チャ：輪斑病(Pestalotia theae)、炭そ病(Colletotrichum theae-sinensis)；
　カンキツ：そうか病(Elsinoe fawcetti)、青かび病(Penicillium italicum)、緑かび病(Penicillium digitatum)、灰色かび病(Botrytis cinerea)、黒点病(Diaporthe citri)、かいよう病(Xanthomonas campestris pv.Citri)；
　コムギ：うどんこ病(Erysiphe graminis f.sp.tritici)、赤かび病(Gibberella zeae)、赤さび病(Puccinia recondita)、褐色雪腐病(Pythium iwayamai)、紅色雪腐病(Monographella nivalis)、眼紋病(Pseudocercosporella herpotrichoides)、葉枯病(Septoria tritici)、ふ枯病(Leptosphaeria nodorum)、雪腐小粒菌核病(Typhula incarnata)、雪腐大粒菌核病(Myriosclerotinia borealis)、立枯病(Gaeumanomyces graminis)； Peach: Monilinia fructicola, black scab (Cladosporium carpophilum), homopsis sp. (Phomopsis sp.);
Sweet cherry: Monilinia fructicola;
Grapes: gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum), downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), brown spot (Pseudocercospora) vitis), black rot (Guignardia bidwellii);
Pear: Black star disease (Venturia nashicola), Red star disease (Gymnosporangium asiaticum), Black spot disease (Alternaria kikuchiana), Ring rot disease (Botryosphaeria berengeriana), Powdery mildew (Phyllactinia mali);
Cha: Ring spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis);
Citrus: scab (Elsinoe fawcetti), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray mold (Botrytis cinerea), black spot (Diaporthe citri), scab (Xanthomonas campestris pv.Citri);
Wheat: powdery mildew (Erysiphe graminis f.sp.tritici), red mold (Gibberella zeae), red rust (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eyeprint Disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow rot microbe nuclei (Typhula incarnata), snow rot microbacilli (Myriosclerotinia borealis), blight (Gaeumanomyces graminis) );
　オオムギ：斑葉病(Pyrenophora graminea)、雲形病(Rhynchosporium secalis)、裸黒穂病(Ustilago tritici、U.nuda)；
　イネ：いもち病(Pyricularia oryzae)、紋枯病(Rhizoctonia solani)、馬鹿苗病(Gibberella fujikuroi)、ごま葉枯病(Cochliobolus miyabeanus)、苗立枯病(Pythium graminicolum)、白葉枯病(Xanthomonas oryzae)、苗立枯細菌病(Burkholderia plantarii)、褐条病(Acidovorax avenae)、もみ枯細菌病(Burkholderia glumae)；
　タバコ：菌核病(Sclerotinia sclerotiorum)、うどんこ病(Erysiphe cichoracearum)；
　チューリップ：灰色かび病(Botrytis cinerea)；
　ベントグラス：雪腐大粒菌核病(Sclerotinia borealis)、赤焼病(Pythium aphanidermatum)；
　オーチャードグラス：うどんこ病(Erysiphe graminis)；
　ダイズ：紫斑病(Cercospora kikuchii)、べと病(Peronospora Manshurica)、茎疫病(Phytophthora sojae)；
　ジャガイモ・トマト：疫病(Phytophthora infestans)；
などの防除に使用することができる。 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: Sclerotinia borealis, Pythium aphanidermatum;
Orchard grass: powdery mildew (Erysiphe graminis);
Soybean: Purpura (Cercospora kikuchii), downy mildew (Peronospora Manshurica), stem rot (Phytophthora sojae);
Potato tomato: Phytophthora infestans;
It can be used for controlling such as.
　また、本発明の農園芸用殺菌剤は、耐性菌に対しても優れた殺菌効果を有する。耐性菌としては、チオファネートメチル、ベノミル、カルベンダジムなどのベンズイミダゾール系殺菌剤に耐性を示す灰色かび病菌（Botrytis cinerea）やテンサイ褐斑病菌（Cercospora beticola）、リンゴ黒星病菌（Venturia inaequalis）、ナシ黒星病菌（Venturia nashicola）；ジカルボキシイミド系殺菌剤（例えば、ビンクロゾリン、プロシミドン、イプロジオン）に耐性を示す灰色かび病菌（Botrytis cinerea）などが挙げられる。 Also, 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.
　本発明の農園芸用殺菌剤の適用がより好ましい病害としては、リンゴの黒星病、キュウリの灰色かび病、コムギのうどんこ病、トマトの疫病、コムギの赤さび病、水稲のいもち病、キュウリのつる割病などが挙げられる。 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.
　また、本発明の農園芸用殺菌剤は薬害が少なく、魚類や温血動物への毒性が低く、安全性の高い薬剤である。
　本発明の農園芸用殺菌剤は、農薬としてとり得る形態、即ち、水和剤、粒剤、粉剤、乳剤、水溶剤、懸濁剤、顆粒水和剤などの農薬製剤の形態で使用することができる。 In addition, 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.
　固体の製剤に用いられる添加剤および担体としては、大豆粉、小麦粉などの植物性粉末、珪藻土、燐灰石、石こう、タルク、ベントナイト、パイロフィライト、クレーなどの鉱物性微粉末、安息香酸ソーダ、尿素、芒硝などの有機および無機化合物などが挙げられる。 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.
　液体の製剤に用いられる溶剤としては、ケロシン、キシレンおよび石油系の芳香族炭化水素、シクロヘキサン、シクロヘキサノン、ジメチルホルムアミド、ジメチルスルホキシド、アルコール、アセトン、トリクロロエチレン、メチルイソブチルケトン、鉱物油、植物油、水などが挙げられる。 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.
　さらに、これらの製剤において均一かつ安定な形態をとるために、必要に応じて界面活性剤を添加することができる。
　添加することができる界面活性剤は特に限定されない。例えば、ポリオキシエチレンが付加したアルキルフェニルエーテル、ポリオキシエチレンが付加したアルキルエーテル、ポリオキシエチレンが付加した高級脂肪酸エステル、ポリオキシエチレンが付加したソルビタン高級脂肪酸エステル、ポリオキシエチレンが付加したトリスチリルフェニルエーテルなどの非イオン性界面活性剤、ポリオキシエチレンが付加したアルキルフェニルエーテルの硫酸エステル塩、アルキルベンゼンスルホン酸塩、高級アルコールの硫酸エステル塩、アルキルナフタレンスルホン酸塩、ポリカルボン酸塩、リグニンスルホン酸塩、アルキルナフタレンスルホン酸塩のホルムアルデヒド縮合物、イソブチレン－無水マレイン酸共重合体などが挙げられる。 Furthermore, in order to take a uniform and stable form in these preparations, a surfactant can be added as necessary.
The surfactant that can be added is not particularly limited. For example, 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.
　このようにして得られた水和剤、乳剤、フロアブル剤、水溶剤、若しくは顆粒水和剤は、水で所定の濃度に希釈して、溶解液、懸濁液あるいは乳濁液として植物に散布するなどして使用することができる。また、粉剤・粒剤はそのまま植物に散布するなどして使用することができる。 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.
　本発明の農園芸用殺菌剤中における有効成分量は、製剤全体に対して、好ましくは０．０１～９０重量％、より好ましくは０．０５～８５重量％である。 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.
　本発明の農園芸用殺菌剤の施用量は、気象条件、製剤形態、施用時期、施用方法、施用場所、防除対象病害、対象作物などにより異なるが、通常１ヘクタール当たり有効成分化合物量にして１～１，０００ｇ、好ましくは１０～１００ｇである。 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.
　水和剤、乳剤、懸濁剤、水溶剤、顆粒水和剤などを水で希釈して施用する場合、その施用濃度は１～１０００ｐｐｍ、好ましくは１０～２５０ｐｐｍである。 When a wettable powder, emulsion, suspension, aqueous solvent, granular wettable powder or the like is diluted with water and applied, the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
　本発明の農園芸用殺菌剤には、他の殺菌剤や殺虫・殺ダニ剤、共力剤を混合することができる。また、本発明の農園芸用殺菌剤と他の殺菌剤や殺虫・殺ダニ剤、共力剤とを同時にまたは相前後して使用することができる。
　このような態様で使用することができる他の殺菌剤、殺虫剤、殺ダニ剤、植物生長調節剤の代表例を以下に示す。 The agricultural and horticultural fungicide of the present invention may be mixed with other fungicides, insecticides / acaricides, and synergists. In addition, 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.
殺菌剤：
（１）ベンゾイミダゾール系：ベノミル、カルベンダジム、フベリダゾール、チアベンダゾール、チオファネート メチル、クロルフェナゾール；
（２）ジカルボキシイミド系：クロゾリネート、イプロジオン、プロシミドン、ビンクロゾリン；
（３）ＤＭＩ－殺菌剤系：イマザリル、オキスポコナゾール、ペフラゾエート、プロクロラズ、トリフルミゾール、トリホリン、ピリフェノックス、フェナリモル、ヌアリモル、アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジフェノコナゾール、ジニコナゾール、エポキシコナゾール、フェンブコナゾール、フルキンコナゾール、フルシラゾール、フルトリアホル、ヘキサコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブタニル、ペンコナゾール、プロピコナゾール、プロチオコナゾール、シメコナゾール、テブコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール、エタコナゾール、ファーコナゾールシス；ジクロブトラゾール、ジニコナゾール－Ｍ、ドデモルフ・アセテート、フルコナゾール、イマザリル・サルフェート、ナフチフェン、ユニコナゾールＰ、ビニコナゾール、ボリコナゾール； 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, prothioconazole, cimeconazole, tebuconazole, tetraconazole, triazimephone, Triadimenol, Triticonazole, Etaconazole, Farconazole cis; Diclobutrazol, Diniconazo Le -M, dodemorph acetate, fluconazole, imazalil-sulphate, Nafuchifen, uniconazole P, Binikonazoru, voriconazole;
（４）フェニルアミド系：ベナラキシル、ベナラキシル－Ｍ、クロジラコン、フララキシル、メタラキシル、メタラキシル－Ｍ、オキサジキシル、オフラセ；
（５）アミン系：アルジモルフ、ドデモルフ、フェンプロピモルフ、トリデモルフ、フェンプロピジン、ピペラリン、スピロキサミン；
（６）ホスホロチオレート系：ＥＤＤＰ、イプロベンホス、ピラゾホス；
（７）ジチオラン系：イソプロチオラン；
（８）カルボキサミド：ベノダニル、ボスカリド、カルボキシン、フェンフラン、フルトラニル、フラメトピル、メプロニル、オキシカルボキシン、ペンチオピラド、チフルザミド、ビキサフェン、イソピラザム、ペンフルフェン、フルキサピロキサド、セダキサン；
（９）ヒドロキシ－（２－アミノ）ピリミジン系：ブピリメート、ジメチリモル、エチリモル； (4) 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) pyrimidine series: bupilimate, dimethylolmol, ethylmol;
（１０）ＡＰ殺菌剤（アニリノピリミジン）系：シプロジニル、メパニピリム、ピリメタニル、アンドプリム；
（１１）Ｎ－フェニルカーバメート系：ジエトフェンカルブ；
（１２）ＱｏＩ－殺菌剤（Ｑｏ阻害剤）系：アゾキシストロビン、ピコキシストロビン、ピラクロストロビン、クレソキシム-メチル、トリフロキシストロビン、ジモキシストロビン、メトミノストロビン、オリザストロビン、ファモキサドン、フルオキサストロビン、フェンアミドン、メトミノフェン；アメトクトラジン、ピラメトストロビン、ピラオキシストロビン、ピリベンカルブ；クメトキシストロビン、クモキシストロビン、エネストロブリン、フェノキシストロビン、トリクロピリカルブ；
（１３）ＰＰ殺菌剤（フェニルピロール）系：フェンピコニル、フルジオキソニル；
（１４）キノリン系：キノキシフェン； (10) AP fungicide (anilinopyrimidine) type: cyprodinil, mepanipyrim, pyrimethanyl, and prim;
(11) N-phenylcarbamate system: Dietophenecarb;
(12) 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: quinoxyphene;
（１５）ＡＨ殺菌剤（芳香族炭化水素）系：ビフェニル、クロロネブ、ジクロラン、キントゼン、テクナゼン、トルクトフォス-メチル；
（１６）ＭＢＩ－Ｒ系：フサライド、ピロキロン、トリシクラゾール；
（１７）ＭＢＩ－Ｄ系：カルプロパミド、ジクロシメット、フェノキサニル；
（１８）ＳＢＩ剤：フェンヘキサミド、ピリブチカルブ、タービナフィン；
（１９）フェニルウレア：ペンシクロン；
（２０）ＱｉＩ－殺菌剤（Ｑｉ阻害剤）：シアゾファミド、アミスルブロム、フルメシクロックス；
（２１）ベンズアミド系：ゾキサミド；
（２２）エノピランウロン系：ブラストサイジン、ミルディオマイシン；
（２３）へキソピラノシル系：カスガマイシン、カスガマイシン塩酸塩；
（２４）グルコピラノシル系：ストレプトマイシン、バリダマイシン、バリダマイシンＡ；
（２５）シアノアセトアミド系：シモキサニル；
（２６）カーバメート系：ヨードカルブ、プロパモカルブ、プロチオカルブ、ポリカーバメート；
（２７）脱共役剤：ビナパクリル、ジノカップ、フェリムゾン、フルアジナム、メプチルジノカップ；
（２８）有機スズ化合物：酢酸トリフェニルスズ、塩化トリフェニルスズ、水酸化トリフェニルスズ； (15) 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: Simoxanyl;
(26) Carbamate series: iodocarb, propamocarb, prothiocarb, polycarbamate;
(27) Uncoupler: Vinapacryl, dinocup, ferrimzone, fluazinam, meptyldinocup;
(28) Organotin compounds: triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide;
（２９）リン酸エステル：亜リン酸、トルクロホスメチル、ホセチル、トルクトフォスメチル；
（３０）フタルアミド酸系：テクロフタラム；
（３１）ベンゾトリアジン系：トリアゾキシド；
（３２）ベンゼンスルフォナミド系：フルスルファミド；
（３３）ピリダジノン：ジクロメジン；
（３４）ＣＡＡ殺菌剤（カルボン酸アミド）系：ジメトモルフ、フルモルフ、ベンチアバリカルブ－イソプロピル、イプロバリカルブ、マンジプロパミド、バリフェナレート；
（３５）テトラサイクリン：オキシテトラサイクリン；
（３６）チオカーバメート系：メタスルホカルブ；
（３７）抵抗性誘導剤：アシベンゾラルＳメチル、プロベナゾール、チアジニル、イソチアニル；
（３８）その他の化合物：エトリジアゾール、ポリオキシン、ポリオクソリム、オキソリニック酸、ヒドロキシイソキサゾール、オクチリノン、シルチオファム、ジフルメトリム、エタボキサム、シフルフェナミド、プロキナジド、メトラフェノン、フルオピコリド、ボルドー液、銅ナフタレート、酸化銅、オキシ塩化銅、硫酸銅、マンコッパー、ビス（８－キノリノラト）銅（ＩＩ）、水酸化第二銅、有機銅、硫黄、多硫化カルシウム、ファーバム、マンゼブ、マンネブ、メチラム、プロピネブ、チウラム、ジネブ、ジラム、キャプタン、カプタホール、フォルペット、クロロタロニル、ジクロフルアニド、トリルフルアニド、ドジン、グアザチン、イミノクタジン、イミノクタジン酢酸塩、イミノクタジンドデシルベンゼンスルホン酸塩、アニラジン、ジチアノン、クロロピクリン、ダゾメット、キノメチオネート、シプロフラム、アグロバクテリウム、フルオルイミド；イソフェタミド、トルプロカルブ、フェンピラザミン、ピリオフェノン、テブフロキン、フルオピラム、ザリラミド；フルオロフォルペット、プロパミジン、エジフェンホス；ベンチアゾール、ベトキサジン、カプサイシン、カルボン、クフラネブ、マンコゼブ、シプロスルファミド、デバカルブ、ジクロロフェン、ジフェンゾクワット、ジフェンゾクワット・メチルスルホネート、ジフェニルアミン、フルメトベル、フルオロイミド、フルチアニル、ホセチル・アルミニウム、ホセチル・カルシウム、ホセチル・ナトリウム、イルママイシン、メチルイソチアネート（ＭＩＴＣ）、ミルデオマイシン、ナタマイシン、ニトロタールイソプロピル、オキサモカルブ、オキシフェンチイン、プロパモカルブ・ホセチレート、プロパモシン・ナトリウム、ピリモルフ、ピロールニトリン、トルニファニド、トリクラミド； (29) Phosphate ester: phosphorous acid, torquelophosmethyl, fosetyl, torquetophosmethyl;
(30) Phthalamic acid type: Teclophthalam;
(31) Benzotriazine type: triazoxide;
(32) benzenesulfonamide series: fursulfamide;
(33) Pyridazinone: Dichromedin;
(34) CAA fungicide (carboxylic acid amide) system: dimethomorph, furmorph, benavalicarb-isopropyl, iprovaricarb, mandipropamide, variphenate;
(35) Tetracycline: oxytetracycline;
(36) Thiocarbamate system: metasulfocarb;
(37) Resistance inducer: acibenzoral S methyl, probenazole, thiazinyl, isothianyl;
(38) Other compounds: etridiazole, polyoxin, polyoxorim, oxolinic acid, hydroxyisoxazole, octirinone, silthiofam, diflumetrim, ethaboxam, cyflufenamide, proquinazide, metolaphenone, fluopicolide, Bordeaux solution, copper naphthalate, copper oxide, copper oxychloride, sulfuric acid Copper, Mancopper, Bis (8-quinolinolato) copper (II), Cupric hydroxide, Organic copper, Sulfur, Calcium polysulfide, Farbum, Manzeb, Mannebu, Methylam, Propineb, Thiuram, Zineb, Zillam, Captan, Captohol , Folpet, chlorothalonil, dichlorfluanide, tolylfluanid, dodine, guazatine, iminoctadine, iminoctadine acetate, iminoctadine dodecylbenzenesulfonate Anilazine, dithianone, chloropicrin, dazomet, quinomethionate, ciprofuram, Agrobacterium, fluorimide; isophetamide, tolprocarb, fenpyrazamine, piophenone, tebufloquine, fluopyram, zaliramide; fluorophorpet, propamidine, edifenphos; Cufraneb, mancozeb, cyprosulfamide, devacarb, dichlorophen, diphenzoquat, diphenzoquat methylsulfonate, diphenylamine, flumethoverl, fluoroimide, flutianil, fosetyl aluminum, fosetyl calcium, fosetyl sodium, ilumamycin , Methyl isothiocyanate (MITC), mildeomycin, na Mycin, nitro tar isopropyl, Okisamokarubu, oxyphencyclimine Ji in, propamocarb-fosetylate, Puropamoshin sodium, Pirimorufu, Pyrrolnitrin, Torunifanido, trichlamide;
殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、駆虫剤：
（１）有機（チオ）ホスフェート系：アセフェート、アザメチホス、アジンホス・メチル、アジンホス・エチル、ブロモホス・エチル、ブロムフェンビンホス、ＢＲＰ、クロルピリホス、クロルピリホス・メチル、クロルピリホス・エチル、クロルフェンビンホス、カズサホス、カルボフェノチオン、クロルエトキシホス、クロルメホス、クマホス、シアノフェンホス、シアノホス、ＣＹＡＰ、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジスルホトン、ジメトン-Ｓ-メチル、ジメチルビンホス、ジメトン－Ｓ－メチルスルホン、ジアリホス、ダイアジノン、ジクロフェンチオン、ジオキサベンゾホス、ジスルホトン、エチオン、エトプロホス、エトリムホス、ＥＰＮ、フェナミホス、フェニトロチオン、フェンチオン、フェンスルホチオン、フルピラゾホス、ホノホス、ホルモチオン、ホスメチラン、ヘプテノホス、イサゾホス、ヨードフェンホス、イソフェンホス、イソキサチオン、イプロベンホス、マラチオン、メビンホス、メタミドホス、メチダチオン、モノクロトホス、メカルバム、メタクリホス、ナレッド、オメトエート、オキシジメトン・メチル、パラオクソン、パラチオン、パラチオン・メチル、フェントエート、ホサロン、ホスメット、ホスファミドン、ホレート、ホキシム、ピリミホス・メチル、ピリミホス・エチル、プロフェノホス、プロチオホス、ホスチアゼート、ホスホカルブ、プロパホス、プロペタムホス、プロトエート、ピリダフェンチオン、ピラクロホス、キナルホス、サリチオン、スルプロホス、スルホテップ、テトラクロルビンホス、テルブホス、トリアゾホス、トリクロルホン、テブピリムホス、テメホス、チオメトン、バミドチオン； Insecticides, acaricides, nematicides, soil insecticides, anthelmintics:
(1) Organic (thio) phosphates: acephate, azamethiphos, azinephos methyl, azinephos ethyl, bromophos ethyl, bromfenbinphos, BRP, chlorpyrifos, chlorpyrifos methyl, chlorpyrifos ethyl, chlorfenvinphos, kazusafos, Carbophenothione, chloroethoxyphos, chlormefos, coumaphos, cyanophenphos, cyanophos, CYAP, diazinon, dichlorvos, dicrotophos, dimethoate, disulfotone, dimeton-S-methyl, dimethylvinphos, dimethone-S-methylsulfone, diariphos, diazinon , Diclofenthion, dioxabenzophos, disulfoton, ethione, etoprophos, etrimfos, EPN, phenamifos, fenitrothion, fenthion, fu Sulfothione, flupyrazophos, phonophos, formothione, phosmethylan, heptenophos, isazophos, iodofenphos, isofenphos, isoxathion, iprobenphos, malathion, mevinphos, methamidophos, methidathion, monocrotophos, mecarbam, methalyphos, nared, ometoate, paramethicone, oxydimethone methyl Parathion, parathion methyl, phentoate, hosalon, phosmet, phosphamidone, folate, phoxime, pyrimifos methyl, pyrimifos ethyl, propenofos, prothiophos, hosthiazate, phosphocarb, propaphos, propetamphos, protoate, pyridafenthione, pyraclophos, quinalphos, phosphatione, sulthione Sulfotep, Tetrachlorbi Nphos, terbufos, triazophos, trichlorfone, tebupyrimfos, temefos, thiometone, bamidithione;
（２）カルバメート系：アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、カルバリル、カルボフラン、カルボスルファン、フェノキシカルブ、フェノチオカルブ、メチオカルブ、メソミル、オキサミル、ピリミカーブ、プロポキスル、チオジカルブ、トリアザメート、エチオフェンカルブ、フェノブカルブ、ＭＩＰＣ、ＭＰＭＣ、ＭＴＭＣ、フラチオカルブ、ＸＭＣ、アルドキシカルブ、アリキシカルブ、アミノカルブ、ブフェンカルブ、ブタカルブ、ブトカルボキシム、ブトキシカルボキシム、クロエトカルブ、ジメチラン、ホルメタネート、イソプロカルブ、メタム・ナトリウム、メトルカルブ、プロメカルブ、チオファノックス、トリメタカルブ、キシリルカルブ； (2) Carbamate series: alanic carb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, phenoxycarb, phenothiocarb, methiocarb, mesomil, oxamyl, pirimicurve, propoxyl, thiodicarb, triazamate, etiofencarb, MPC, MC , MTMC, furthiocarb, XMC, aldoxicarb, alixicarb, aminocarb, bufencarb, butacarb, butcarboxyme, butoxycarboxyme, cloetocarb, dimethylane, formethanate, isoprocarb, metam sodium, metocarb, promecarb, thiophanox, trimetacarb, xylylcarb ;
（３）ピレトロイド系：アレトリン、ビフェントリン、シフルトリン、ベータ・シフルトリン、シハロトリン、ラムダ・シハロトリン、シフェノトリン、シペルメトリン、アルファ・シペルメトリン、ベータ・シペルメトリン、ゼタ・シペルメトリン、デルタメトリン、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、イミプロトリン、ペルメトリン、プラレトリン、ピレトリン、ピレトリンＩ、ピレトリンＩＩ、レスメトリン、シラフルオフェン、フルバリネート、テフルトリン、テトラメトリン、トラロメトリン、トランスフルトリン、プロフルトリン、ジメフルトリン、アクリナトリン、シクロプロトリン、ハルフェンプロックス、フルシトリネート、ビオアレスリン、ビオエタノメトリン、ビオペルメトリン、ビオレスメトリン、トランスペルメトリン、エンペントリン、フェンフルトリン、フェンピリトリン、フルブロシトリネート、フルフェンプロックス、フルメトリン、メトフルトリン、フェノトリン、プロトリフェンブト、ピレスメトリン、テラレトリン； (3) Pyrethroids: alletrin, bifenthrin, cyfluthrin, beta cyfluthrin, cyhalothrin, lambda cyhalothrin, ciphenothrin, cypermethrin, alpha cypermethrin, beta cypermethrin, zeta cypermethrin, deltamethrin, esfenvalerate, eth Fenprox, fenpropatoline, fenvalerate, imiprothrin, permethrin, praretrin, pyrethrin, pyrethrin I, pyrethrin II, resmethrin, silafluophene, fulvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, promethrin , Halfenprox, flucitrinate, bioareslin, bioethanomethrin, Oh permethrin, bioresmethrin, trans permethrin, empenthrin, fenfluthrin Trinh, Fen pyridinium Trinh, full Bro shea tri sulphonate, full Fen flufenprox, flumethrin, metofluthrin, phenothrin, protrifenbute, pyresmethrin, terallethrin;
（４）成長調節物質：
（ａ）キチン合成阻害剤：クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、テフルベンズロン、トリフルムロン、ビストリフルロン、ノビフルムロン、ブプロフェジン、ヘキシチアゾクス、エトキサゾール、クロフェンテジン、フルアズロン、ペンフルロン；
（ｂ）エクジソンアンタゴニスト：ハロフェノジド、メトキシフェノジド、テブフェノジド、クロマフェノジド、アザジラクチン；
（ｃ）幼若ホルモン様物質： ピリプロキシフェン、メトプレン、ジオフェノラン、エポフェノナン、ハイドロプレン、キノプレン、トリプレン；
（ｄ）脂質生合成阻害剤：スピロジクロフェン、スピロメシフェン、スピロテトラマト、フロニカミド； (4) Growth regulator:
(A) Chitin synthesis inhibitor: chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, nobarulone, teflubenzuron, triflumuron, bistrifluron, nobiflumuron, buprofezin, hexithiazox, etoxazole, clofente Gin, fluazuron, penfluron;
(B) ecdysone antagonists: halofenozide, methoxyphenozide, tebufenozide, chromafenozide, azadirachtin;
(C) juvenile hormone-like substances: pyriproxyfen, metoprene, geophenolan, epofenanane, hydroprene, quinoprene, triprene;
(D) Lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramat, flonicamid;
（５）ニコチン受容体アゴニスト／アンタゴニスト化合物：アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム、ニチアジン、ニコチン、ベンスルタップ、カルタップ、フルピラジフロン；
（６）ＧＡＢＡアンタゴニスト化合物：
（ａ）アセトプロール、エチプロール、フィプロニル、バニリプロール、ピラフルプロール、ピリプロール；
（ｂ）有機塩素系：カンフェクロル、クロルデン、エンドスルファン、ＨＣＨ、γ－ＨＣＨ、ヘプタクロル、メトキシクロル；
（７）大環状ラクトン殺虫剤：アバメクチン、エマメクチン安息香酸塩、ミルベメクチン、レピメクチン、スピノサド、イベルメクチン、セラメクチン、ドラメクチン、エピノメクチン、モキシデクチン、ミルベマイシン、ミルベマイシンオキシム；
（８）ＭＥＴＩ Ｉ化合物：フェナザキン、ピリダベン、テブフェンピラド、トルフェンピラド、フルフェネリム、ヒドラメチルノン、フェンピロキシメート、ピリミジフェン、ジコホル；
（９）ＭＥＴＩ ＩＩおよびＩＩＩ化合物：アセキノシル、フルアクリピリム、ロテノン；
（１０）脱共役剤化合物：クロルフェナピル、ビナパクリル、ジノブトン、ジノカップ、ＤＮＯＣ； (5) Nicotine receptor agonist / antagonist compounds: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nithiazine, nicotine, bensultap, cartap, flupiradiflon;
(6) GABA antagonist compound:
(A) acetoprole, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole;
(B) Organochlorine: camfechlor, chlordane, endosulfan, HCH, γ-HCH, heptachlor, methoxychlor;
(7) Macrocyclic lactone insecticide: abamectin, emamectin benzoate, milbemectin, lepimectin, spinosad, ivermectin, selamectin, doramectin, epinomectin, moxidectin, milbemycin, milbemycin oxime;
(8) METI I compounds: phenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, hydramethylnon, fenpyroximate, pyrimidifen, dicophor;
(9) METI II and III compounds: acequinosyl, fluacrylpyrim, rotenone;
(10) Uncoupler compounds: chlorfenapyr, binapacryl, dinobutone, dinocup, DNOC;
（１１）酸化的リン酸化阻害剤化合物：シヘキサチン、ジアフェンチウロン、フェンブタチン・オキシド、プロパルギット、アゾシクロチン；
（１２）脱皮かく乱化合物：シロマジン；
（１３）混合機能オキシダーゼ阻害剤化合物：ピペロニルブトキシド；
（１４）ナトリウムチャネル遮断剤化合物：インドキサカルブ、メタフルミゾン；
（１５）微生物農薬：ＢＴ剤、昆虫病原ウイルス剤、昆虫病原糸状菌剤、線虫病原糸状菌剤；バチルス属種、白きょう病菌、黒きょう病菌、ペキロマイセス属種、チューリンギエンシン、バーティシリウム属種；
（１６）ラトロフィリン受容体作用薬：デプシペプチド、環状デプシペプチド、２４員環状デプシペプチド、エモデプシド；
（１７）オクトパミン性作用薬：アミトラズ；
（１８）リアノジン誘導体作用薬：フルベンジアミド、クロラントラニリプロール、シアントラリニプロール；
（１９）マグネシウム刺激性ＡＴＰアーゼの阻害薬：チオシクラム、チオスルタップ、ネライストキシン；
（２０）摂食阻害薬：ピメトロジン；
（２１）ダニ成長阻害薬：クロフェンテジン、エトキサゾール；
（２２）その他の化合物：ベンクロチアズ、ビフェナゼート、ピリダリル、硫黄、シエノピラフェン、シフルメトフェン、アミドフルメット、テトラジホン、クロルジメホルム、１，３－ジクロロプロペン、ＤＣＩＰ、フェニソブロモレート、ベンゾメート、メタアルデヒド、スピネトラム、ピリフルキナゾン、ベンゾキシメート、ブロモプロピレート、キノメチオネート、クロルベンジレート、クロルピクリン、クロチアゾベン、ジシクラニル、フェノキサクリム、フェントリファニル、フルベンジミン、フルフェンジン、ゴシップルア、ジャポニルア、メトキサジアゾン、石油、オレイン酸カリウム、スルフルラミド、テトラスル、トリアラセン；アフィドピロペン（afidopyropen）、ピフルブミド（pyflubumide）、フロメトキン、フルフィプロル（flufiprole）、フルエンスルフォン、メペルフルスリン、テトラメチルフルスリン、スルホキサフロール、イミシアホス、トラロピリル、ジフロビダジン、ジメフルスリン、メチルネオデカンアミド；
（２３）駆虫剤：
（ａ）ベンズイミダゾール系：フェンベンダゾール、アルベンダゾール、トリクラベンダゾール、オキシベンダゾール；
（ｂ）サリチルアニリド系：クロサンテル、オキシクロザニド；
（ｃ）置換フェノール系：ニトロキシニル；
（ｄ）ピリミジン系：ピランテル；
（ｅ）イミダゾチアゾール系：レバミソール；
（ｆ）テトラヒドロピリミジン：プラジカンテル；
（ｇ）その他の駆虫薬：シクロジエン、リアニア、クロルスロン、メトロニダゾール； (11) 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: Amitraz;
(18) Ryanodine derivative agonist: fulbenzamide, chlorantraniliprole, cyantraliniprol;
(19) Inhibitors of magnesium-stimulated ATPase: thiocyclam, thiosultap, nereistoxin;
(20) antifeedant: pymetrozine;
(21) Tick growth inhibitor: clofentezin, etoxazole;
(22) Other compounds: Benclothiaz, Bifenazate, Pyridalyl, Sulfur, Sienopyraphene, Ciflumethofene, Amidoflumet, Tetradiphone, Chlordimeform, 1,3-Dichloropropene, DCIP, Phenisobromolate, Benzate, Metaaldehyde, Spinetram, Pyrifluquinazone, Benzene Axipodene (Afidopyropen), piflubumide, furometokin, fulphip Le (flufiprole), full-ene sulfone, Meperufurusurin, tetramethyl full Surin, sulfo hexa Flore, Imishiahosu, Toraropiriru, Jifurobidajin, Jimefurusurin, methyl neo decanoic amide;
(23) Anthelmintic:
(A) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole;
(B) Salicylanilide series: closantel, oxyclozanide;
(C) substituted phenolic: nitroxinyl;
(D) pyrimidine series: pyrantel;
(E) imidazothiazole series: levamisole;
(F) tetrahydropyrimidine: praziquantel;
(G) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole;
植物生長調節剤：
　アブシジン酸、インドール酪酸、ウニコナゾール、エチクロゼート、エテホン、クロキシホナック、クロルメコート、クロレラ抽出液、過酸化カルシウム、シアナミド、ジクロルプロップ、ジベレリン、ダミノジッド、デシルアルコール、トリネキサパックエチル、メピコートクロリド、パクロブトラゾール、パラフィンワックス、ピペロニルブトキシド、ピラフルフェンエチル、フルルプリミドール、プロヒドロジャスモン、プロヘキサジオンカルシウム塩、ベンジルアミノプリン、ペンディメタリン、ホルクロルフェニュロン、マレイン酸ヒドラジドカリウム、１－ナフチルアセトアミド、４－ＣＰＡ、ＭＣＰＢ、コリン、硫酸オキシキノリン、エチクロゼート、ブトルアリン、1-メチルシクロプロペン、アビグリシン塩酸塩； 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;
　次に、実施例を挙げて本発明を更に詳細に説明するが、本発明は以下の実施例により何ら限定されるものではない。 Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples.
実施例１
　８－フルオロ－３－（３－フルオロ－２－イソオキサゾール－３－イルフェノキシ）－キノリンの製造方法
〔工程１〕 Example 1
Process for producing 8-fluoro-3- (3-fluoro-2-isoxazol-3-ylphenoxy) -quinoline [Step 1]
Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019
　２－フルオロ－６－（８－フルオロキノリン－３－イルオキシ）ベンズアルデヒド　オキシム０．４２ｇをＮ，Ｎ－ジメチルホルムアミド４ｍＬに溶解させた。該溶液を５０℃に加温し、これにＮ－クロロコハク酸イミド０．１９ｇを加えて２．５時間反応させた。次いで、この反応溶液に、エチニルトリメチルシラン０．１８ｇを加えて、０℃に冷却した。次いで、この反応溶液に、トリエチルアミン０．１８ｇをＮ，Ｎ－ジメチルホルムアミド１．４ｍＬに溶解させた溶液を滴下し、滴下終了後室温に戻し、そのまま５時間反応させた。その後、反応溶液を酢酸エチルと水で分液し、有機相を水洗し、硫酸マグネシウムで乾燥させた。これをろ過し、濃縮した。その後、シリカゲルカラムクロマトグラフィーで精製して、８－フルオロ－３－［３－フルオロ－２－（５－トリメチルシリルイソオキサゾール－３－イル）フェノキシ］－キノリン０．４７ｇを得た。
〔工程２〕 0.42 g of 2-fluoro-6- (8-fluoroquinolin-3-yloxy) benzaldehyde oxime was dissolved in 4 mL of N, N-dimethylformamide. The solution was warmed to 50 ° C., and 0.19 g of N-chlorosuccinimide was added thereto and reacted for 2.5 hours. Next, 0.18 g of ethynyltrimethylsilane was added to the reaction solution and cooled to 0 ° C. Next, a solution prepared by dissolving 0.18 g of triethylamine in 1.4 mL of N, N-dimethylformamide was added dropwise to the reaction solution. After completion of the dropwise addition, the solution was returned to room temperature and allowed to react for 5 hours. Thereafter, the reaction solution was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. This was filtered and concentrated. Thereafter, the residue was purified by silica gel column chromatography to obtain 0.47 g of 8-fluoro-3- [3-fluoro-2- (5-trimethylsilylisoxazol-3-yl) phenoxy] -quinoline.
[Step 2]
Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020
　８－フルオロ－３－［３－フルオロ－２－（５－トリメチルシリルイソオキサゾール－３－イル）フェノキシ］－キノリン０．３０ｇをアセトニトリル４．５ｍＬおよびエタノール１．５ｍＬの混合溶媒に溶解させた。この溶液にフッ化セシウム０．１６ｇを加えて、室温で１時間撹拌した。その後、反応溶液に飽和塩化アンモニウム水溶液を加えて、反応を停止させた。この溶液を酢酸エチルと水で分液し、有機相を水洗し、硫酸マグネシウムで乾燥させた。これをろ過し、濃縮した。その後、シリカゲルカラムクロマトグラフィーで精製して、８－フルオロ－３－（３－フルオロ－２－イソオキサゾール－３－イルフェノキシ）－キノリン０．１２ｇを得た。 8-fluoro-3- [3-fluoro-2- (5-trimethylsilylisoxazol-3-yl) phenoxy] -quinoline (0.30 g) was dissolved in a mixed solvent of 4.5 mL of acetonitrile and 1.5 mL of ethanol. Cesium fluoride 0.16g was added to this solution, and it stirred at room temperature for 1 hour. Then, saturated ammonium chloride aqueous solution was added to the reaction solution, and reaction was stopped. This solution was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. This was filtered and concentrated. Thereafter, the resultant was purified by silica gel column chromatography to obtain 0.12 g of 8-fluoro-3- (3-fluoro-2-isoxazol-3-ylphenoxy) -quinoline.
実施例２
　８－フルオロ－３－（３－フルオロ－２－オキサゾール－５－イルフェノキシ）－２－メチルキノリンの製造方法 Example 2
Process for producing 8-fluoro-3- (3-fluoro-2-oxazol-5-ylphenoxy) -2-methylquinoline
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
　２－フルオロ－６－（８－フルオロ－２－メチルキノリン－３－イルオキシ）ベンズアルデヒド０．３２ｇ、およびｐ－トルエンスルホニルメチルイソシアニド０．２１ｇをメタノール３．２ｍＬに溶解させた。この溶液に炭酸カリウム０．１５ｇを室温で加え、次いで、撹拌しながら４．５時間加熱還流した。その後、反応溶液を室温に戻し、溶媒を留去した。得られた残渣を酢酸エチルと水で分液し、有機相を水洗し、硫酸マグネシウムで乾燥させた。これをろ過し、濃縮した。その後、シリカゲルカラムクロマトグラフィーで精製して、８－フルオロ－３－（３－フルオロ－２－オキサゾール－５－イルフェノキシ）－２－メチルキノリン０．２７ｇを得た。 2-Fluoro-6- (8-fluoro-2-methylquinolin-3-yloxy) benzaldehyde (0.32 g) and p-toluenesulfonylmethyl isocyanide (0.21 g) were dissolved in methanol (3.2 mL). To this solution, 0.15 g of potassium carbonate was added at room temperature, and then heated to reflux with stirring for 4.5 hours. Then, the reaction solution was returned to room temperature and the solvent was distilled off. The obtained residue was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. This was filtered and concentrated. Thereafter, the residue was purified by silica gel column chromatography to obtain 0.27 g of 8-fluoro-3- (3-fluoro-2-oxazol-5-ylphenoxy) -2-methylquinoline.
実施例３
　８－フルオロ－３－（３－フルオロ－２－フラン－３－イルフェノキシ）－キノリンの製造方法 Example 3
Process for producing 8-fluoro-3- (3-fluoro-2-furan-3-ylphenoxy) -quinoline
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022
　８－フルオロ－３－（３－フルオロ－２－ヨードフェノキシ）－キノリン０．５０ｇ、フラン－３－ボロン酸ピナコールエステル０．２５ｇ、［１，１’－ビス（ジフェニルホスフィノ）フェロセン］パラジウム（ＩＩ）ジクロリド０．１１ｇおよびリン酸カリウム０．５５ｇを、１，４－ジオキサン１０ｍＬおよび水２ｍＬの混合溶媒に溶解させた。この溶液を撹拌しながら５時間加熱還流した。その後、反応溶液を酢酸エチルと水で分液し、有機相を水洗し、硫酸マグネシウムで乾燥させた。これをろ過し、濃縮した。その後、シリカゲルカラムクロマトグラフィーで精製して、８－フルオロ－３－（３－フルオロ－２－フラン－３－イルフェノキシ）－キノリン０．２７ｇを得た。 8-fluoro-3- (3-fluoro-2-iodophenoxy) -quinoline 0.50 g, furan-3-boronic acid pinacol ester 0.25 g, [1,1′-bis (diphenylphosphino) ferrocene] palladium ( II) 0.11 g of dichloride and 0.55 g of potassium phosphate were dissolved in a mixed solvent of 10 mL of 1,4-dioxane and 2 mL of water. The solution was heated to reflux with stirring for 5 hours. Thereafter, the reaction solution was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over magnesium sulfate. This was filtered and concentrated. Thereafter, the residue was purified by silica gel column chromatography to obtain 0.27 g of 8-fluoro-3- (3-fluoro-2-furan-3-ylphenoxy) -quinoline.
　上記の実施例で得られた含窒素ヘテロ環化合物、および上記の実施例のいずれかと同様の手法によって合成することができる含窒素ヘテロ環化合物を、第１表～第４表に示す。表中の記号は式（５）～式（８）で表される化合物の置換基である。Ｐｙはピリジンを意味する。物性の欄には、融点（℃）、屈折率（ｎＤ）、性状（Amr.はアモルファス、Oilは常温で油状であることを意味する。）をそれぞれ示す。 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. In the column of physical properties, melting point (° C.), refractive index (nD), and properties (Amr. Means amorphous and Oil means oil at normal temperature) are shown.
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000031
　上記の表に示した化合物について1Ｈ－ＮＭＲ(CDCl3, δppm)を測定した。測定結果の一部を以下に示す。
　化合物１－１　：　6.94 (d, 1H, J = 8.4 Hz), 7.12 (m, 1H), 7.28-7.32 (m, 2H), 7.38-7.46 (m, 4H), 7.79 (m, 1H), 8.54 (m, 1H), 8.69 (d, 1H, J = 2.8 Hz), 8.72 (s, 1H).
　化合物１－５　：　6.89 (d, 1H, J = 8.4 Hz), 7.11 (m, 1H), 7.32-7.53 (m, 7H), 8.41 (d, 1H, 5.2 Hz), 8.72 (d, 1H, J = 2.8 Hz).
　化合物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)
　化合物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)
　化合物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).
　化合物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).
　化合物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).
　化合物１－２１　：　2.38 (s, 3H), 2.70 (s, 3H), 6.18 (s, 1H), 6.82 (d, 1H), 7.07 (t, 1H), 7.22-7.44 (m, 5H)
　化合物２－１　：　4.09-4.15 (m, 1H), 4.34 (t, 1H), 5.70 (t, 1H), 6.69 (d, 1H), 6.94 (t, 1H), 7.24-7.36 (m, 2H), 7.48-7.50 (m, 2H), 7.64 (s, 1H), 8.84 (d, 1H)
　化合物２－８　：　6.48 (d, 1H), 6.99-7.03 (m, 1H), 7.26-7.34 (m, 1H), 7.37-7.44 (m, 5H), 8.44 (d, 1H), 8.71 (d, 1H)
　化合物２－９　：　0.28 (s, 9H), 6.49 (s, 1H), 7.04 (t, 1H), 7.26-7.28 (m, 1H), 7.39-7.47 (m, 5H), 8.69 (d, 1H)
　化合物２－１１　：　7.03 (d, 1H), 7.29-7.48 (m, 7H), 7.91 (s, 1H), 8.76 (d, 1H)
　化合物２－１２　：　6.96 (d, 1H), 7.14 (dd, 1H), 7.25-7.46 (m, 5H), 8.09 (d, 1H), 8.85 (d, 1H)
　化合物２－１３　：　4.02 (s, 3H), 6.89 (d, 1H), 7.10 (t, 1H), 7.32-7.38 (m, 1H), 7.47-7.54 (m, 4H), 7.74 (s, 1H), 8.67 (d, 1H)
　化合物２－２４　：　2.62(s, 3H), 6.86 (dd, 1H), 7.25-7.35 (m, 5H), 7.57-7.61 (m, 2H), 7.92 (s, 1H)
　化合物２－２６　：　2.01 (s, 3H), 6.93 (d, 1H), 7.12 (t, 1H), 7.28-7.33 (m, 1H), 7.45-7.52 (m, 4H), 8.24 (d, 1H), 8.74 (d, 1H)
　化合物２－４５　：　2.00 (m, 1H), 2.14-2.30 (m, 2H), 2.46 (m, 1H), 3.70-3.75(m, 2H), 6.89 (d, J = 8.4 Hz, 1H), 7.07 (m, 1H), 7.30-7.36 (m, 2H), 7.43-7.50 (m, 2H), 7.61 (m, 1H), 8.87 (d, J = 2.8 Hz, 1H) 1 H-NMR (CDCl 3 , δ ppm) of the compounds shown in the above table was measured. Some of the measurement results are shown below.
Compound 1-1: 6.94 (d, 1H, J = 8.4 Hz), 7.12 (m, 1H), 7.28-7.32 (m, 2H), 7.38-7.46 (m, 4H), 7.79 (m, 1H), 8.54 (m, 1H), 8.69 (d, 1H, J = 2.8 Hz), 8.72 (s, 1H).
Compound 1-5: 6.89 (d, 1H, J = 8.4 Hz), 7.11 (m, 1H), 7.32-7.53 (m, 7H), 8.41 (d, 1H, 5.2 Hz), 8.72 (d, 1H, J = 2.8 Hz).
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).
Compound 1-21: 2.38 (s, 3H), 2.70 (s, 3H), 6.18 (s, 1H), 6.82 (d, 1H), 7.07 (t, 1H), 7.22-7.44 (m, 5H)
Compound 2-1: 4.09-4.15 (m, 1H), 4.34 (t, 1H), 5.70 (t, 1H), 6.69 (d, 1H), 6.94 (t, 1H), 7.24-7.36 (m, 2H) , 7.48-7.50 (m, 2H), 7.64 (s, 1H), 8.84 (d, 1H)
Compound 2-8: 6.48 (d, 1H), 6.99-7.03 (m, 1H), 7.26-7.34 (m, 1H), 7.37-7.44 (m, 5H), 8.44 (d, 1H), 8.71 (d, 1H)
Compound 2-9: 0.28 (s, 9H), 6.49 (s, 1H), 7.04 (t, 1H), 7.26-7.28 (m, 1H), 7.39-7.47 (m, 5H), 8.69 (d, 1H)
Compound 2-11: 7.03 (d, 1H), 7.29-7.48 (m, 7H), 7.91 (s, 1H), 8.76 (d, 1H)
Compound 2-12: 6.96 (d, 1H), 7.14 (dd, 1H), 7.25-7.46 (m, 5H), 8.09 (d, 1H), 8.85 (d, 1H)
Compound 2-13: 4.02 (s, 3H), 6.89 (d, 1H), 7.10 (t, 1H), 7.32-7.38 (m, 1H), 7.47-7.54 (m, 4H), 7.74 (s, 1H) , 8.67 (d, 1H)
Compound 2-24: 2.62 (s, 3H), 6.86 (dd, 1H), 7.25-7.35 (m, 5H), 7.57-7.61 (m, 2H), 7.92 (s, 1H)
Compound 2-26: 2.01 (s, 3H), 6.93 (d, 1H), 7.12 (t, 1H), 7.28-7.33 (m, 1H), 7.45-7.52 (m, 4H), 8.24 (d, 1H) , 8.74 (d, 1H)
Compound 2-45: 2.00 (m, 1H), 2.14-2.30 (m, 2H), 2.46 (m, 1H), 3.70-3.75 (m, 2H), 6.89 (d, J = 8.4 Hz, 1H), 7.07 (m, 1H), 7.30-7.36 (m, 2H), 7.43-7.50 (m, 2H), 7.61 (m, 1H), 8.87 (d, J = 2.8 Hz, 1H)
（製剤）
　次に、本発明に係る農園芸用殺菌剤の実施例を若干示すが、添加物および添加割合は、これら実施例に限定されるべきものではなく、広範囲に変化させることが可能である。また、製剤実施例中の部は重量部を示す。 (Formulation)
Next, some examples of the agricultural and horticultural fungicide according to the present invention are shown. However, the additive and the addition ratio are not limited to these examples, and can be changed in a wide range. Moreover, the part in a formulation Example shows a weight part.
製剤実施例１　　　　水和剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　４０部
　　クレー　　　　　　　　　　　　　　　　　　　　４８部
　　ジオクチルスルホサクシネートナトリウム塩　　　　４部
　　リグニンスルホン酸ナトリウム塩　　　　　　　　　８部
　以上を均一に混合して微細に粉砕し、有効成分４０％の水和剤を得る。 Formulation Example 1 Wetting agent Nitrogen-containing heterocyclic compound of the present invention 40 parts Clay 48 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts The above ingredients are uniformly mixed and finely pulverized, and the active ingredient 40 % Wettable powder is obtained.
製剤実施例２　　　　乳剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　１０部
　　ソルベッソ２００　　　　　　　　　　　　　　　５３部
　　シクロヘキサノン　　　　　　　　　　　　　　　２６部
　　ドデシルベンゼンスルホン酸カルシウム塩　　　　　１部
　　ポリオキシエチレンアルキルアリルエーテル　　　１０部
　以上を混合溶解し、有効成分１０％の乳剤を得る。 Formulation Example 2 Emulsion Nitrogen-containing heterocyclic compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts An emulsion containing 10% active ingredient by mixing and dissolving the above. Get.
製剤実施例３　　　　粉剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　１０部
　　クレー　　　　　　　　　　　　　　　　　　　　９０部
　以上を均一に混合して微細に粉砕し、有効成分１０％の粉剤を得る。 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.
製剤実施例４　　　　粒剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　　５部
　　クレー　　　　　　　　　　　　　　　　　　　　７３部
　　ベントナイト　　　　　　　　　　　　　　　　　２０部
　　ジオクチルスルホサクシネートナトリウム塩　　　　１部
　　リン酸カリウム　　　　　　　　　　　　　　　　　１部
　以上をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分５％の粒剤を得る。 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.
製剤実施例５　　　　懸濁剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　１０部
　　ポリオキシエチレンアルキルアリルエーテル　　　　４部
　　ポリカルボン酸ナトリウム塩　　　　　　　　　　　２部
　　グリセリン　　　　　　　　　　　　　　　　　　１０部
　　キサンタンガム　　　　　　　　　　　　　　　０．２部
　　水　　　　　　　　　　　　　　　　　　　　７３．８部
　以上を混合し、粒度が３ミクロン以下になるまで湿式粉砕し、有効成分１０％の懸濁剤を得る。 Formulation Example 5 Suspending agent 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.
製剤実施例６　　　　顆粒水和剤
　　本発明の含窒素ヘテロ環化合物　　　　　　　　　４０部
　　クレー　　　　　　　　　　　　　　　　　　　　３６部
　　塩化カリウム　　　　　　　　　　　　　　　　　１０部
　　アルキルベンゼンスルホン酸ナトリウム塩　　　　　１部
　　リグニンスルホン酸ナトリウム塩　　　　　　　　　８部
　　アルキルベンゼンスルホン酸ナトリウム塩のホルムアルデヒド縮合物
　　　　　　　　　　　　　　　　　　　　　　　　　　５部
　以上を均一に混合して微細に粉砕後、適量の水を加えてから練り込んで粘土状にする。粘土状物を造粒した後乾燥し、有効成分４０％の顆粒水和剤を得る。 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.
（生物試験例１）リンゴ黒星病防除試験
　製剤実施例２において得られた乳剤を有効成分１００ｐｐｍの濃度に希釈した。素焼きポットで栽培したリンゴ幼苗（品種「国光」、３～４葉期）に前記希釈液を散布し、室温で自然乾燥した。その後、リンゴ黒星病菌（Venturia inaequalis）の分生胞子を接種し、明暗を１２時間毎に繰り返す２０℃、高湿度の室内に２週間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を求めた。
　化合物番号１－１、１－４、１－５、１－６、１－７、１－９、１－１１、１－１２、１－１６、１－１８、１－１９、２－１、２－２、２－７、２－８、２－１０、２－１１、２－１６、２－１７、２－２０、２－２１、２－２２、２－２３、２－２４、２－２６、２－３０、２－３５、２－３７、２－３８、２－３９、２－４１、２－４２、２－４４、２－４５、および３－１の化合物についてリンゴ黒星病防除試験を行った結果、いずれの化合物も７５％以上の防除価を示した。 (Biological Test Example 1) Apple scab control test The emulsion obtained in Formulation Example 2 was diluted to a concentration of 100 ppm active ingredient. The diluted solution was sprayed on apple seedlings (variety “Kunimitsu”, 3-4 leaf stage) cultivated in an unglazed pot and allowed to air dry at room temperature. Then, conidia of apple scab (Venturia inaequalis) were inoculated, and the light and darkness was repeated every 12 hours and kept in a room at 20 ° C. and high humidity for 2 weeks. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
Compound Nos. 1-1, 1-4, 1-5, 1-6, 1-7, 1-9, 1-11, 1-12, 1-16, 1-18, 1-19, 2-1, 2-2, 2-7, 2-8, 2-10, 2-11, 2-16, 2-17, 2-20, 2-21, 2-22, 2-23, 2-24, 2- 26, 2-30, 2-35, 2-37, 2-38, 2-39, 2-41, 2-42, 2-44, 2-45, and 3-1 compounds for apple scab control As a result, all the compounds showed a control value of 75% or more.
（生物試験例２）キュウリ灰色かび病防除試験
　製剤実施例２において得られた乳剤を有効成分１００ｐｐｍの濃度に希釈した。素焼きポットで栽培したキュウリ幼苗（品種「相模半白」、子葉期）に前記希釈液を散布し、室温で自然乾燥した。その後、キュウリ灰色かび病菌（Botrytis cinerea）の分生胞子懸濁液を滴下接種し、２０℃、高湿度の暗室内に４日間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を求めた。
　化合物番号１－９、１－１０、１－１４、１－２０、１－２２、１－２２、２－２、２－８、２－１０、２－１１、２－２１、２－２２、２－２３、２－２４、２－２６、２－２９、２－３０、２－３４、２－３５、２－３６、２－３７、２－３８、２－３９、２－４１、２－４２、２－４４、および３－１の化合物についてキュウリ灰色かび病防除試験を行った結果、いずれの化合物も７５％以上の防除価を示した。 (Biological Test Example 2) Cucumber Gray Mold Control Test The emulsion obtained in Formulation Example 2 was diluted to a concentration of 100 ppm active ingredient. The diluted solution was sprayed on cucumber seedlings grown in an unglazed pot (variety “Sagamihanjiro”, cotyledon stage) and air-dried at room temperature. Thereafter, a conidial spore suspension of Botrytis cinerea was inoculated dropwise and kept in a dark room at 20 ° C. and high humidity for 4 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
Compound Nos. 1-9, 1-10, 1-14, 1-20, 1-22, 1-22, 2-2, 2-8, 2-10, 2-11, 2-21, 2-22, 2-23, 2-24, 2-26, 2-29, 2-30, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-41, 2- As a result of performing a cucumber gray mold control test on the compounds 42, 2-44, and 3-1, all the compounds showed a control value of 75% or more.
　これらの結果から、本発明の含窒素ヘテロ環化合物は、殺菌性能を示し、農園芸用殺菌剤の有効成分として有用であることがわかる。 These results show that the nitrogen-containing heterocyclic compound of the present invention exhibits bactericidal performance and is useful as an active ingredient of agricultural and horticultural fungicides.

Claims (7)

  1. 　式（１）：
    Figure JPOXMLDOC01-appb-C000001
    式（１）中、
    　Ｃｙは、無置換の若しくは置換基を有するオキシラニル基、または無置換の若しくは置換基を有する５～６員ヘテロ環基を示し；
    　Ｂは、窒素原子または炭素原子を示し；
    　Ｄは、５～７員炭化水素環または５～７員ヘテロ環を示し；
    　Ｘ１は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有する５～６員ヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示し；
    　ｍは、Ｘ１の個数を示し、０～６のいずれかの整数であり；
    　Ｅは、５～７員炭化水素環または５～７員ヘテロ環を示し；
    　Ｘ２は、それぞれ独立に、無置換の若しくは置換基を有するＣ１～８アルキル基、無置換の若しくは置換基を有するＣ２～８アルケニル基、無置換の若しくは置換基を有するＣ２～８アルキニル基、無置換の若しくは置換基を有するＣ３～８シクロアルキル基、無置換の若しくは置換基を有するＣ４～８シクロアルケニル基、無置換の若しくは置換基を有するＣ６～１０アリール基、無置換の若しくは置換基を有する５～６員ヘテロ環基、無置換の若しくは置換基を有するＣ１～８アシル基、無置換の若しくは置換基を有する（１－イミノ）Ｃ１～８アルキル基、無置換の若しくは置換基を有するカルボキシル基、無置換の若しくは置換基を有するカルバモイル基、無置換の若しくは置換基を有する水酸基、無置換の若しくは置換基を有するアミノ基、無置換の若しくは置換基を有するメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、またはニトロ基を示し；
    　ｎは、Ｘ２の個数を示し、０～４のいずれかの整数であり；
    　Ｘは、酸素原子、硫黄原子、－Ｃ（＝Ｏ）－基で表される基、または－ＣＨＯＨ－基で表される基を示す、
    で表される含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物。     Formula (1):
    Figure JPOXMLDOC01-appb-C000001
    In formula (1),
    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 heterocycle;
    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 unsubstituted or substituted mercapto group, a substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group;
    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 heterocycle;
    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 group, an unsubstituted or substituted mercapto group, a substituted sulfonyl group, a halogeno group, a cyano group, or a nitro group;
    n represents the number of X 2 and is an integer of 0 to 4;
    X represents an oxygen atom, a sulfur atom, a group represented by a —C (═O) — group, or a group represented by a —CHOH— group.
    Or a salt or N-oxide compound thereof.
  2. 　前記式（１）が、式（２）：
    Figure JPOXMLDOC01-appb-C000002
    式（２）中、
    　Ｃｙ、Ｘ１、ｍ、Ｘ２、ｎ、Ｂ、およびＸは、前記式（１）中のそれぞれと同じ意味を示し；
    　Ａ１、Ａ２、Ａ３、およびＡ４は、それぞれ独立して、炭素原子または窒素原子を示す、
    で表されることを特徴とする請求項１に記載の含窒素ヘテロ環化合物またはその塩若しくはＮ－オキサイド化合物。     Formula (1) is converted to Formula (2):
    Figure JPOXMLDOC01-appb-C000002
    In formula (2),
    Cy, X 1 , m, X 2 , n, B, and X have the same meaning as in formula (1);
    A 1 , A 2 , A 3 , and A 4 each independently represent a carbon atom or a nitrogen atom,
    The nitrogen-containing heterocyclic compound or a salt thereof or an N-oxide compound thereof according to claim 1, wherein
  3. 　前記式（１）が、式（３）：
    Figure JPOXMLDOC01-appb-C000003
    式（３）中、
    　Ｃｙ、Ｘ１、ｍ、Ｘ２、Ｂ、およびＸは、前記式（１）中のそれぞれと同じ意味を示し；
    　ｎ１は、Ｘ２の個数を示し、０～３のいずれかの整数であり；
    　Ａ５、Ａ６、およびＡ７は、それぞれ独立して、炭素原子、窒素原子、酸素原子、または硫黄原子を示すが、酸素原子同士、硫黄原子同士、酸素原子と硫黄原子の組合わせが隣接することはない、
    で表されることを特徴とする請求項１に記載の含窒素ヘテロ環化合物またはその塩若しくはＮ－オキサイド化合物。     Formula (1) is converted to Formula (3):
    Figure JPOXMLDOC01-appb-C000003
    In formula (3),
    Cy, X 1 , m, X 2 , B and X have the same meaning as in formula (1);
    n1 represents the number of X 2 and is an integer of 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, but oxygen atoms, sulfur atoms, or a combination of oxygen and sulfur atoms are adjacent to each other Never do,
    The nitrogen-containing heterocyclic compound or a salt thereof or an N-oxide compound thereof according to claim 1, wherein
  4. 　前記式（１）が、式（４）：
    Figure JPOXMLDOC01-appb-C000004
    　式（４）中、Ｃｙ、Ｘ１、ｍ、Ｘ２、ｎ、およびＤは、前記式（１）中のそれぞれと同じ意味を示す、
    で表される請求項１に記載の含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物。     Formula (1) is converted to Formula (4):
    Figure JPOXMLDOC01-appb-C000004
    In the formula (4), Cy, X 1 , m, X 2 , n, and D have the same meaning as in the formula (1).
    The nitrogen-containing heterocyclic compound according to claim 1, represented by the formula: or a salt or N-oxide compound thereof.
  5. 　式（４）中のＤがベンゼン環である、請求項４に記載の含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物。 The nitrogen-containing heterocyclic compound according to claim 4, or a salt or N-oxide compound thereof, wherein D in the formula (4) is a benzene ring.
  6. 　Ｃｙが、無置換の若しくは置換基を有するオキシラニル基、無置換の若しくは置換基を有する５員ヘテロアリール基、無置換の若しくは置換基を有する６員へテロアリール基、無置換の若しくは置換基を有する部分不飽和の５員ヘテロ環基、無置換の若しくは置換基を有する部分不飽和の６員へテロ環、基無置換の若しくは置換基を有する飽和５員ヘテロ環基、または無置換の若しくは置換基を有する飽和６員へテロ環基である、請求項１～５のいずれか１項に記載の含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物。 Cy has 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 Partially unsaturated 5-membered heterocyclic group, unsubstituted or substituted partially unsaturated 6-membered heterocycle, group unsubstituted or substituted saturated 5-membered heterocyclic group, or unsubstituted or substituted The nitrogen-containing heterocyclic compound according to any one of claims 1 to 5, which is a saturated 6-membered heterocyclic group having a group, or a salt or N-oxide compound thereof.
  7. 　請求項１～６のいずれか１項に記載の含窒素ヘテロ環化合物、またはその塩若しくはＮ－オキサイド化合物から選ばれる少なくとも１種を有効成分として含有する農園芸用殺菌剤。 An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the nitrogen-containing heterocyclic compound according to any one of claims 1 to 6, or a salt thereof, or an N-oxide compound.
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