WO2010026771A1 - Nitrogenated heterocyclic compound and salt thereof, and bactericidal agent for agricultural or horticultural applications - Google Patents

Nitrogenated heterocyclic compound and salt thereof, and bactericidal agent for agricultural or horticultural applications Download PDF

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Publication number
WO2010026771A1
WO2010026771A1 PCT/JP2009/004395 JP2009004395W WO2010026771A1 WO 2010026771 A1 WO2010026771 A1 WO 2010026771A1 JP 2009004395 W JP2009004395 W JP 2009004395W WO 2010026771 A1 WO2010026771 A1 WO 2010026771A1
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group
substituent
optionally substituted
compound
substituted
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PCT/JP2009/004395
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French (fr)
Japanese (ja)
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三谷晃
稲垣準
▲桑▼原頼人
横山雅裕
柴山耕太郎
佐藤元亮
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日本曹達株式会社
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Priority to JP2010527708A priority Critical patent/JP5281647B2/en
Publication of WO2010026771A1 publication Critical patent/WO2010026771A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms

Definitions

  • the present invention relates to a novel nitrogen-containing heterocyclic compound and a salt thereof, and an agricultural and horticultural fungicide containing at least one of these compounds as an active ingredient.
  • control agents are used against crop diseases, but their control efficacy is insufficient, their use is restricted by the emergence of drug-resistant pathogens, and From the viewpoints of causing phytotoxicity and pollution to plants, or toxicity to human and livestock fish and impact on the environment, there are many things that are not necessarily satisfactory control agents. Accordingly, there is a strong demand for the emergence of such a drug that can be safely used with few defects.
  • Patent Documents 1 and 2 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. However, the compounds of the present invention are not described.
  • the present invention relates to a novel nitrogen-containing heterocyclic compound and a salt thereof, which can be an active ingredient of an agricultural and horticultural fungicide that is reliable and can be used safely, and contains at least one of these compounds as an active ingredient. It is an object to provide a disinfectant.
  • the present invention provides a nitrogen-containing heterocyclic compound represented by the following formula (I) or a salt thereof.
  • X is a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, a C2-12 alkynyl group which may have a substituent, a substituted A C3-12 cycloalkyl group which may have a group, a C4-12 cycloalkenyl group which may have a substituent, a C8-12 cycloalkynyl group which may have a substituent, and a substituent.
  • An optionally substituted heterocyclic group an optionally substituted C1-12 acyl group, an optionally substituted (1-imino) C1-12 alkyl group, an optionally substituted hydroxyl group, a substituted
  • An amino group which may have a group, a mercapto group which may have a substituent, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
  • m represents an integer of 0 to 6. When m is 2 or more, Xs may be the same or different from each other. X substituted on adjacent atoms may be taken together to form a 5- to 8-membered ring which may have a substituent.
  • R has a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, a C2-12 alkynyl group which may have a substituent, and a substituent.
  • An optionally substituted C3-12 cycloalkyl group, an optionally substituted C4-12 cycloalkenyl group, an optionally substituted C8-12 cycloalkynyl group, an optionally substituted C6-12 12 represents an aryl group, an optionally substituted heterocyclic group, an optionally substituted C1-12 acyl group, or a substituted sulfonyl group.
  • Q represents a C6-12 aryl group which may have a substituent, or a heterocyclic group which may have a substituent.
  • A independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and n represents an integer of 1 or 2.
  • a solid line and a dotted double line indicate a single bond or a double bond. ) Or a salt thereof.
  • A is a carbon atom, n is 2, and an unsaturated ring is formed through a double bond.
  • a compound or a salt thereof is preferred.
  • a compound of the following formula (III) or a salt thereof in which Q is a benzene ring is more preferable.
  • X ′ is independently a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, or a C2-12 alkynyl group which may have a substituent.
  • s represents an integer of 0 to 5. When s is 2 or more, X ′ may be the same as or different from each other. X ′ substituted on adjacent atoms may be taken together to form a 5- to 8-membered ring which may have a substituent.
  • the present invention also provides an agricultural and horticultural fungicide containing as an active ingredient at least one compound of the present invention or a salt thereof.
  • the nitrogen-containing heterocyclic compounds and salts thereof of the present invention are novel compounds and are useful as active ingredients of agricultural and horticultural fungicides that can be used safely and reliably.
  • the agricultural and horticultural fungicide of the present invention is an agent that has an excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to human and livestock fish and environmental impact.
  • Nitrogen-containing heterocyclic compound represented by the formulas (I) to (III) or a salt thereof The compound of the present invention is a nitrogen-containing heterocyclic compound represented by the formula (I) to (III) or a salt thereof. is there.
  • the compound of the present invention or a salt thereof includes hydrates, various solvates and crystal polymorphs.
  • the compounds of the present invention include stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures thereof.
  • C1-12 alkyl group of “optionally substituted C1-12 alkyl group” for R, X and X ′ means a linear or branched alkyl group having 1 to 12 carbon atoms. To do.
  • C2-12 alkenyl group in the “optionally substituted C2-12 alkenyl group” for R, X and X ′ is a carbon having a carbon-carbon double bond at any one or more positions in the alkyl group. It means a linear or branched alkenyl group having 2 to 12.
  • C2-12 alkynyl group of “optionally substituted C2-12 alkynyl group” for R, X and X ′ is the number of carbon atoms having a carbon-carbon triple bond at any one or more positions of the alkyl group. It means 2 to 12 linear or branched alkynyl groups.
  • C3-12 cycloalkyl group” of “optionally substituted C3-12 cycloalkyl group” for R, X and X ′ means an alkyl group having 3-12 carbon atoms having a cyclic portion.
  • a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like can be given. Of these, C3-6 cycloalkyl groups are preferred.
  • C4-12 cycloalkenyl group of “optionally substituted C4-12 cycloalkenyl group” for R, X and X ′ means an alkenyl group having 4 to 12 carbon atoms having a cyclic portion. Examples thereof 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. Of these, C4-8 cycloalkenyl groups are preferred.
  • C8-12 cycloalkynyl group of “optionally substituted C8-12 cycloalkynyl group” for R, X and X ′ means an alkynyl group having 8-12 carbon atoms having a cyclic portion.
  • 5-cyclooctynyl group, 6-cyclodecynyl group and the like can be mentioned.
  • the “C6-12 aryl group” in the “optionally substituted C6-12 aryl group” for R, Q, and X ′ means a monocyclic or polycyclic aryl group having 6 to 12 carbon atoms. .
  • a partially saturated group is included in addition to the fully unsaturated group. Examples thereof include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group. Of these, a phenyl group is preferred.
  • heterocyclic group of the “optionally substituted heterocyclic group” for R, Q, X and X ′ is selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom as a ring-constituting atom.
  • C1-12 acyl group” of “optionally substituted C1-12 acyl group” for R, X and X ′ is a hydrogen atom, a linear or branched C1-11 alkyl group, linear or Branched C2-11 alkenyl group, straight chain or branched C2-11 alkynyl group, monocyclic or polycyclic C6-10 aryl group, or nitrogen atom other than carbon atoms as atoms constituting the ring And a 5- to 7-membered heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom and a sulfur atom means a group bonded to a carbonyl group.
  • formyl group acetyl group, propionyl group, n-propylcarbonyl group, n-butylcarbonyl group, pentanoyl group, valeryl group, octanoyl group, nonanoyl group, decanoyl group, i-propylcarbonyl group, i-butylcarbonyl group, Alkylcarbonyl groups such as pivaloyl group, isovaleryl group, 3-methylnonanoyl group, 8-methylnonanoyl group, 3-ethyloctanoyl group; alkenylcarbonyl groups such as acryloyl group, methacryloyl group; alkynylcarbonyl groups such as propioroyl group; benzoyl group, Examples thereof include arylcarbonyl groups such as naphthylcarbonyl group, biphenylcarbonyl group and anthranylcarbonyl group; heterocyclic carbonyl groups such
  • the “(1-imino) C1-12 alkyl group” in the “optionally substituted (1-imino) C1-12 alkyl group” of X and X ′ is a linear or branched C1-11
  • An alkyl group means a group bonded to an iminomethyl group.
  • iminomethyl group for example, iminomethyl group, (1-imino) ethyl group, (1-imino) propyl group, (1-imino) butyl group, (1-imino) pentyl group, (1-imino) hexyl group, (1-imino)
  • Examples include heptyl group, (1-imino) octylimino group, (1-imino) isobutyl group, (1-imino) isopentyl group, (1-imino) neopentyl group and the like.
  • (1-imino) C1-6 alkyl groups are preferred.
  • halogeno group examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • C1-12 alkyl group substituted by the “optionally substituted C3-12 cycloalkyl group” in the “optionally substituted C1-12 alkyl group” of R, X and X ′
  • Examples of "" include a cyclopropylmethyl group, a 2-cyclopropylethyl group, a cyclopentylmethyl group, a 2-cyclohexylethyl group, a 2-cyclooctylethyl group, and the like. Of these, C4-10 cycloalkyl C1-6 alkyl groups are preferred.
  • C1-12 alkyl group substituted by the “optionally substituted C4-12 cycloalkenyl group” in the “optionally substituted C1-12 alkyl group” of R, X and X ′
  • C1-12 alkyl group substituted by the “optionally substituted C8-12 cycloalkynyl group” in the “optionally substituted C1-12 alkyl group” of R, X and X ′ "Includes, for example, a 5-cyclooctynylmethyl group and the like. Of these, C8-10 cycloalkynyl C1-6 alkyl groups are preferred.
  • the “C1-12 alkyl group” substituted by the “halogeno group” includes, for example, a fluoromethyl group, a chloromethyl group, and the like.
  • C1-12 alkyl group substituted by “optionally substituted C6-12 aryl group” in “optionally substituted C1-12 alkyl group” for R, X and X ′
  • Examples thereof include benzyl group, phenethyl group, 3-phenylpropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group and the like. Of these, C6-12 aryl C1-6 alkyl groups are preferred.
  • the “C1-12 alkyl group” substituted by the “optionally substituted heterocyclic group” For example, 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-pyrazylmethyl group, 3-pyrazylmethyl group, 2- (2-pyrazyl) ethyl group 2- (3-pyrazyl) ethyl group, 3- (2-pyrazyl) propyl group, 3- (3-pyrazyl) propyl group, 2-pyrimidylmethyl group, 4-pyrimidylmethyl group, 2-pyrimidylmethyl group, 4-pyrimidylmethyl group, 4-pyr
  • the “C1-12 alkyl group” substituted by the “hydroxyl group” means that “having a substituent” A hydroxy C1-12 alkyl group ”, and examples thereof include a hydroxymethyl group, a hydroxyethyl group, and a hydroxypropyl group. Of these, hydroxy C1-6 alkyl groups are preferred.
  • the “hydroxy C1-12 alkyl group” substituted by “C1-12 alkyl group optionally having substituent” includes: For example, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, Examples thereof include a t-butoxyethyl group. Of these, C1-6 alkoxy C1-6 alkyl groups are preferred.
  • the “hydroxy C1-12 alkyl group optionally having substituent” substituted by “C1-12 acyl group optionally having substituent” examples include formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group and the like. Of these, C2-7 acyloxy C1-6 alkyl groups are preferred.
  • C3-12 cycloalkyl substituted by “optionally substituted C1-12 alkyl group” in “optionally substituted C3-12 cycloalkyl group” for R, X and X '
  • groups of the “group” include 2,3,3-trimethylcyclobutyl group, 4,4,6,6-tetramethylcyclohexyl group, 1,3-dibutylcyclohexyl group and the like. Of these, C4-10 cycloalkyl groups in which 1 to 3 C1-6 alkyls are substituted are preferred.
  • C4-12 cycloalkenyl group substituted by “optionally substituted C1-12 alkyl group” in “optionally substituted C4-12 cycloalkenyl group” for R, X and X ′
  • groups of the “group” include 2-methyl-3-cyclohexenyl group, 3,4-dimethyl-3-cyclohexenyl group and the like. Of these, a C5-9 cycloalkenyl group in which 1 to 3 C1-6 alkyl is substituted is preferable.
  • C8-12 cycloalkynyl substituted by “optionally substituted C1-12 alkyl group” in “optionally substituted C8-12 cycloalkynyl group” of R, X and X ′
  • groups of the “group” include 2,3-diethyl-4-cyclodecynyl group. Of these, a C8-10 cycloalkynyl group in which 1 to 3 C1-6 alkyl is substituted is preferable.
  • the “C2-12 alkenyl group” substituted by the “halogeno group” includes, for example, 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 Examples include -2-propenyl group, 3,3-difluoro-2-propenyl group, 2,4,6-trichloro-2-hexenyl group, and the like. Of these, C2-6 alkenyl groups substituted with 1 to 3 halogen atoms are preferred.
  • the “C2-12 alkynyl group” substituted by the “halogeno group” includes, for example, 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, 5, Examples include a 5-dichloro-2-methyl-3-pentynyl group, a 4-chloro-1,1-dimethyl-2-butynyl group, and the like. Of these, C2-6 alkynyl groups substituted with 1 to 3 halogen atoms are preferred.
  • the “hydroxyl group” substituted by the “optionally substituted C1-12 alkyl group” means that C1-12 alkoxy group ”, for example, methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, decyloxy group, i-propoxy group I-butoxy group, s-butoxy group, t-butoxy group, 1-ethylpropoxy group, isohexyloxy 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-dimethylbutoxy group Group, 2,3-dimethylbutoxy group, 1-ethylbutoxy group,
  • alkoxy group substituted by “optionally C6-12 aryl group” examples include cyclopropylmethyloxy group, 2-cyclopentylethyloxy group, benzyloxy group and the like. Of these, C1-7 alkoxy groups are preferred.
  • Examples of the “group” in which the “alkoxy group” is substituted with the “halogeno group” include, for example, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1 -Difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group and the like. Of these, C1-6 alkoxy groups substituted with 1 to 3 halogen atoms are preferred.
  • the “hydroxyl group” substituted by “optionally substituted C2-12 alkenyl group” means that A C2-12 alkenyloxy group which may be, for example, vinyloxy group, 1-propenyloxy group, 2-propenyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group.
  • the “hydroxyl group” substituted by the “optionally substituted C2-12 alkynyl group” means that in the “C2-12 alkynyloxy group”
  • the “hydroxyl group having a substituent” in X and X ′ means the “C3-12 cycloalkoxy group”. Examples thereof include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group, and further, “C1-12 alkyl optionally having substituent (s)”
  • the cycloalkoxy group substituted by “group” include, for example, 2-methylcyclopropyloxy group, 2-ethylcyclopropyloxy group, 2,3,3-trimethylcyclobutyloxy group, 2-methylcyclopentyloxy group 2-ethylcyclohexyloxy group, 2-ethylcyclooctyloxy group, 4 4,6,6-
  • the “hydroxyl group having a substituent” in X and X ′ the “hydroxyl group” substituted by the “optionally substituted C6-12 aryl group”, that is, “may have a substituent” C6-12 aryloxy group ”, for example, phenyloxy group, naphthyloxy group, azulenyloxy group, indenyloxy group, indanyloxy group, tetralinyloxy group and the like. Of these, C6-12 aryloxy groups are preferred.
  • the “hydroxyl group having a substituent” of X and X ′ may have a substituent” C1-12 acyloxy group ", for example, acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, pentanoyloxy Group, pivaloyloxy group and the like. Of these, C1-6 acyloxy groups are preferred.
  • the “C1-12 acyl group” substituted by the “halogeno group” includes, for example, a monofluoroacetyl group, monochloro Acetyl group, monobromoacetyl group, difluoroacetyl group, dichloroacetyl group, dibromoacetyl group, trifluoroacetyl group, trichloroacetyl group, tribromoacetyl group, 3,3,3-trifluoropropionyl group, 3,3,3 -Trichloropropionyl group, 2,2,3,3,3-pentafluoropropionyl group and the like.
  • C1-6 acyl groups substituted with 1 to 3 halogen atoms are preferred.
  • the optionally substituted C1 acyl group is replaced by “the substituted hydroxyl group” "Is a" carboxyl group having a substituent ".
  • examples of the “carboxyl group” substituted by the “optionally substituted C1-12 alkyl group” include, for example, a methoxycarbonyl group, an ethoxycarbonyl group, and n-propoxy group.
  • Examples include a carbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, decyloxycarbonyl group and the like.
  • examples of the “alkyl-substituted carboxyl group” substituted by “optionally substituted C3-12 cycloalkyl group” or “optionally substituted C6-12 aryl group” include, for example, cyclo Examples include propylmethyloxycarbonyl group, 2-cyclopentylethyloxycarbonyl group, benzyloxycarbonyl group and the like. Of these, C1-7 alkoxycarbonyl groups are preferred.
  • the hydrogen atom on the hydroxyl group is substituted with the “optionally substituted C1-12 alkyl group”.
  • the “group” include methoxyiminomethyl group, (1-ethoxyimino) methyl group, (1-ethoxyimino) ethyl group, and the like. Of these, (1- (C1-6 alkoxy) imino) C1-6 alkyl groups are preferred.
  • Examples of the “amino group” substituted by the “optionally substituted C1-12 alkyl group” in the “optionally substituted amino group” of X and X ′ include, for example, a methylamino group , Ethylamino group, dimethylamino group, diethylamino group and the like. Of these, a mono C1-6 alkylamino group or a di C1-6 alkylamino group is preferable.
  • Examples of the “group” in which two hydrogen atoms on the amino group are substituted with the same carbon atom of the “optionally substituted C1-12 alkyl group” include, for example, a methylideneamino group and an ethylideneamino group Etc.
  • mono C1-6 alkylideneamino groups are preferred.
  • monoarylamino groups such as phenylamino group and 4-methylphenylamino group (preferably monoC6-12 arylamino group); diarylamino groups such as di1-naphthylamino group (preferably Are diC6-12 arylamino groups); acylamino groups such as acetylamino group and benzoylamino group (preferably C1-6 acylamino groups).
  • the substituted C1-12 acyl group is replaced by “the substituted amino group” "Is a" carbamoyl group having a substituent ".
  • the substituted amino group having a substituent examples of the “carbamoyl group” substituted by the “optionally substituted C1-12 alkyl group” include, for example, a methylcarbamoyl group, an ethylcarbamoyl group, a dimethylcarbamoyl group And diethylcarbamoyl group.
  • a mono C1-6 alkylcarbamoyl group or a diC1-6 alkylcarbamoyl group is preferable.
  • carbamoyl group for example, carbamoyl group; monoarylcarbamoyl group such as phenylcarbamoyl group and 4-methylphenylcarbamoyl group (preferably mono C6-12 arylcarbamoyl group); acyl such as acetylcarbamoyl group and benzoylcarbamoyl group And a rucarbamoyl group (preferably a C1-6 acylcarbamoyl group).
  • Examples of the “mercapto group” substituted by the “optionally substituted C1-12 alkyl group” in the “optionally substituted mercapto group” for X and X ′ include, for example, a methylthio group, An ethylthio group etc. are mentioned. Of these, C1-6 alkylthio groups are preferred.
  • an arylthio group such as a phenylthio group and a 4-methylphenylthio group (preferably a C6-12 arylthio group), an acylthio group such as an acetylthio group and a benzoylthio group (preferably a C1-6 acylthio group) )
  • an arylthio group such as a phenylthio group and a 4-methylphenylthio group (preferably a C6-12 arylthio group)
  • an acylthio group such as an acetylthio group and a benzoylthio group (preferably
  • Examples of the “sulfonyl group” substituted by the “optionally substituted C1-12 alkyl group” in the “sulfonyl group having a substituent” of R, X and X ′ include, for example, a methylsulfonyl group, ethyl Sulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, s-butylsulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, isopentylsulfonyl group, neopentylsulfonyl group 1-ethylpropylsulfonyl group, n-hexylsulfonyl group, isohexylsulfonyl group and
  • C1-6 alkylsulfonyl groups are preferred.
  • 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 a C6- 12 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 Sulfamoyl groups such as N, N-dimethylsulfamoyl group
  • substituent of “having a substituent” or “may have a substituent”, other than the above, for example, —Si (Me) 3 , —SiPh 3 , -Si (c Pr) 3, -Si (Me) 2 (t Bu) (t Bu represents a tertiary butyl group. hereinafter the same.), such as -Si (R 1) (R 2 ) (R 3) Group represented by these.
  • A independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and n represents an integer of 1 or 2.
  • a solid line and a dotted double line indicate a single bond or a double bond. That is, the ring containing A is a 5-membered or 6-membered ring, and forms a saturated ring, a partially unsaturated ring, or an unsaturated ring.
  • the salt of the compound of the present invention is not particularly limited as long as it is an agriculturally and horologically acceptable salt.
  • 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; iron and copper
  • salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like.
  • the compound represented by the formula (1) is lithiated using an alkyl lithium reagent, and the compound represented by the formula (2) is added to produce the compound represented by the formula (3).
  • the alkyllithium reagent used include methyllithium, n-butyllithium, s-butyllithium, t-butyllithium, lithium diisopropylamide (LDA), and the like.
  • LDA lithium diisopropylamide
  • an anhydrous reaction system can be constructed, and the compound to be used can be used without limitation unless it dissolves the compound and does not react or have any special interaction.
  • Preferred examples include alkanes such as pentane, hexane, heptane, Isopar (registered trademark) E, and Isopar (registered trademark) G, aromatics such as benzene, toluene, and orthoxylene, and ethers such as diethyl ether and THF.
  • alkanes such as pentane, hexane, heptane, Isopar (registered trademark) E, and Isopar (registered trademark) G
  • aromatics such as benzene, toluene, and orthoxylene
  • ethers such as diethyl ether and THF.
  • a solvent and a mixture of these solvents can be used, and ether solvents such as diethyl ether and THF are preferred.
  • ether solvents such as diethyl ether and THF are preferred.
  • it can be made anhydrous in a nitrogen atmosphere or the like and can be prepared at
  • a compound represented by the formula (4) is produced by oxidizing the compound represented by the formula (3).
  • the oxidation reaction can be performed without any particular limitation as long as it is a reaction capable of oxidizing the secondary hydroxyl group. Examples thereof include an oxidation method such as Jones oxidation, ozone oxidation, and Swern oxidation, or a method using an oxidation reagent such as manganese dioxide and Dess-Martin reagent.
  • the compound represented by the formula (III) of the present invention is produced by dehydrating and condensing the compound represented by the formula (4) and the compound represented by the formula (5) to produce an oxime.
  • the formation of the oxime is carried out in a known manner in a solvent such as ethanol by reaction with the compound of formula (5) or its hydrochloride, optionally in a base such as pyridine, sodium acetate or aqueous sodium hydroxide solution.
  • a solvent such as ethanol
  • a base such as pyridine, sodium acetate or aqueous sodium hydroxide solution.
  • the present invention also provides an agricultural and horticultural fungicide containing, as an active ingredient, at least one of the nitrogen-containing heterocyclic compounds represented by the formulas (I) to (III) of the present invention or salts thereof. (Hereafter, it may be called "the present invention bactericide").
  • the fungicide of the present invention contains the compound of the present invention as an active ingredient, and a wide variety of filamentous fungi such as algae (Omycetes), Ascomycetes, Deuteromycetes, basidiomycetes It has excellent bactericidal power against bacteria belonging to (Basidiomycetes).
  • filamentous fungi such as algae (Omycetes), Ascomycetes, Deuteromycetes, basidiomycetes). It has excellent bactericidal power against bacteria belonging to (Basidiomycetes).
  • the fungicide of the present invention can be used by seed treatment, foliage spraying, soil application, water application, etc., for the control of various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf and grass.
  • Sugar beet brown spot (Cercospora beticola) Black root disease (Aphanomyces cochlloides) Peanut brown spot (Mycosphaerella arachidis) Black astringent disease (Mycosphaerella berkeleyi) Cucumber powdery mildew (Sphaerotheca furiginea) Vine Blight (Mycosphaella melonis) Sclerotinia sclerotiorum Gray mold disease (Botrytis cinerea) Black star disease (Cladosporium cucumerinum) Brown spot disease (Corynespora casiccola) Seedling Blight (Phythium debaryanam, Rhizoctonia solani Kuhn) Spotted bacterial disease (Pseudomonas syringae pv.
  • Tomato gray mold (Botrytis cinerea) Leaf mold (Cladosporium fulvum) Eggplant gray mold (Botrytis cinerea) Black blight (Corynespora melogenae) Powdery mildew (Erysiphe cichoracerarum) Susmolder disease (Mycovellosi natrassii) Strawberry Gray mold disease (Botrytis cinerea) Powdery mildew (Sohaerotheca humuli) Anthracnose (Colletotrichum acutatum, Colletotrichum fragariae) Onion gray rot (Botrytis allii) Gray mold disease (Botrytis cinerea) White spotted leaf blight (Botrytis squamosa) Cabbage root-knot disease (Plasmodiophora brassicae) Soft rot (Erwinia carotovora) Kidney bean sclerotia (Sclerotinia sclerotiorum
  • Peach out ash scab (Monilinia fracticola) Grapes Gray mold (Botrytis cinerea) Powdery mildew (Uncinula necator) Late rot (Glomerella cingulata) Pear black scab (Venturia nashicola) Red Star Disease (Gymnosporium asiaticum) Black spot disease (Alternaria kikuchiana) Cha ring spot disease (Pestaloti theae) Colletotrichum theae-sinensis citrus scab (Elsinoe fawceti) Blue mold disease (Penicillium italicum) Green mold (Penicillium digitatum) Gray mold disease (Botrytis cinerea) Black spot disease (Diaporthe citri) Sickness disease (Xanthomonas campestris pv.
  • Citri Wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) Red mold disease (Gibberella zeae) Red rust (Puccinia recondita) Brown snow rot (Pythium iwayamai) Scarlet Snow Rot (Monographella nivalis) Eye disease (Pseudocercosporella herpotriochoides) Leaf blight (Septoria tritici) Blight disease (Leptosphaeria nodorum) Typhula incarnata (Typhula incarnata) Snow rot large mycobacterial disease (Myriosclerotinia borealis) Blight (Gaeumanomyces graminis)
  • Barley leaf spot (Pyrenophora graminea) Rhynchosporium secalis Bare Scab (Ustilago tritici, U. nuda) Rice blast disease (Pyricularia oryzae) Rhizoctonia solani Idiot Seedling (Gibberella fujikuroi) Sesame leaf blight (Cochliobolus niyabeanus) Seedling blight (Pythium gramicolium) Tobacco sclerotia (Sclerotinia sclerotiorum) Powdery mildew (Erysiphe cichoracerarum) Botrytis cinerea Bentgrass Snow rot large sclerotia nuclear disease (Sclerotinia borealis) Red fire disease (Pythium aphanidermatum) Orchardgrass powdery mildew (Erysiphe graminis) Soybean Purpura (Cercospora kiku
  • the bactericidal agent of the present invention has an excellent bactericidal effect not only on pathogenic bacteria sensitive to these drugs but also on resistant bacteria.
  • gray mold fungus (Botrytis cinerea), sugar beet brown fungus (Cercospora beticola), Venturia inaequalis, Venturia inaquali (Venturia inaequalis), Nent black urinaria (Venturia inaequilis)
  • the fungicides of the present invention are also effective against).
  • the fungicides of the present invention are also effective against gray mold fungi (Botrytis cinerea) that are resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione).
  • Favorable diseases that can be applied include brown spot of sugar beet, powdery mildew of wheat, rice blast, rice black spot, gray mold of cucumber, and brown spot of peanut.
  • the fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
  • a form that can be taken by a general pesticide for the purpose of use as an agrochemical, , Wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, granular wettable powders and the like.
  • Additives and carriers that can be added to the agrochemical formulation include vegetable powders such as soybean flour and wheat flour, diatomaceous earth, apatite, gypsum, talc, bentonite, and pyrophyllite for solid dosage forms.
  • Organic and inorganic compounds such as mineral fine powders such as clay, sodium benzoate, urea, and sodium sulfate are used.
  • kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, Water or the like can be used as a solvent.
  • a surfactant may be added as necessary.
  • the surfactant that can be added is not particularly limited.
  • alkylphenyl ether added with polyoxyethylene alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, polyoxyethylene Sorbitan higher fatty acid ester added with polyoxyethylene, nonionic surfactant such as tristyryl phenyl ether added with polyoxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfuric acid of higher alcohol
  • ester salts alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and isobutylene-maleic anhydride copolymers.
  • the wettable powder, emulsion, flowable powder, aqueous solvent, and granular wettable powder thus obtained are diluted with water to a predetermined concentration and sprayed as a solution, suspension, or emulsion. Granules are used as they are sprayed on plants.
  • the amount of the active ingredient in the fungicide of the present invention is usually preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the entire composition (formulation).
  • the application amount of the fungicide of the present invention varies depending on weather conditions, formulation form, application time, application method, application location, disease to be controlled, target crop, etc., but usually 1 to 1,000 g in terms of the amount of the active ingredient compound per hectare. It is preferably 10 to 100 g.
  • the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
  • one or two or more of various fungicides, insecticides / miticides, and synergists can be mixed with the fungicide of the present invention.
  • fungicides insecticides, acaricides, and plant growth regulators that can be used in combination with the compounds of the present invention are shown below.
  • Fungicide Benzimidazoles such as benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl; Dicarboximides such as clozolinate, iprodione, procymidone, vinclozolin; Imazaril, oxpoconazole, pefazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, full Quinconazole, flusilazole, flutriazole, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, prothioconazole, cimeconazole,
  • Phenylamides such as benalaxyl, furaxyl, metalaxyl, metalaxyl-M, oxadixyl, and ophthalase; Amines such as aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; Phosphorothiolate systems such as EDDP, iprobenphos, pyrazophos; Dithiolanes such as isoprothiolane; Carboxamides such as benodanyl, boscalid, carboxin, fenfuran, flutolanil, furametopyr, mepronyl, oxycarboxyl, penthiopyrad, tifluzamide; hydroxy- (2-amino) pyrimidines such as buprimate, dimethylylmol, ethylimyl; AP fungicide (anilinopyrimidine); N-phenylc
  • Insecticides and acaricides Organophosphorus and carbamate insecticides: Fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formothione, marathon, trichlorfone, thiometone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimethone methyl, ethion, salicione, cyanophos, isoxathione, cyanophos, isoxathione Methidathione, Sulprophos, Chlorfenvinphos, Tetrachlorbinphos, Dimethylvinphos, Propafos, Isophenphos, Ethylthiomethone, Profenofos, Piracrofos, Monocrotophos, Adinfosmethyl, Aldicarb, Mesomil, Thiodicarb, Carbofuran, Carbo
  • Pyrethroid insecticides Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, thoramethrin , Silafluophene, brofenprox, aclinasrin, etc.
  • Benzoylurea and other insecticides Diflubenzuron, Chlorfluazuron, Hexaflumuron, Triflumuron, Tetrabenzuron, Flufenoxuron, Flucycloxuron, Buprofezin, Pyriproxyfen, Metoprene, Benzoepine, Diafenthiuron, Acetamiprid, Imidacloprid, Nitenpyram, Fipronil, Cartap Thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.
  • Nematicides Phenamifos, phostiazates, etc.
  • Acaricide Chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexithiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor etc.
  • 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 hydrazide maleate, 1- Naphtylacetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozeate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride.
  • the present invention will be described in more detail by way of examples.
  • the present invention is not limited to the following examples.
  • corresponds to the compound number in the table
  • reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried over magnesium sulfate.
  • reaction solution was poured into water, insolubles were filtered off, extracted with ethyl acetate, and the organic layer was washed with water.
  • Example of this invention disinfectant is shown a few, an additive and an addition ratio should not be limited to these Examples, and can be changed in a wide range. Moreover, the part in a formulation Example shows a weight part.
  • Formulation Example 1 Wetting agent Compound of the present invention 40 parts Clay 48 parts Dioctylsulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts or more are uniformly mixed and finely pulverized, and 40% active ingredient wettable powder Get.
  • Emulsion Compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts or more are mixed and dissolved to obtain an emulsion containing 10% active ingredient.
  • Formulation Example 3 Powder A compound of the present invention 10 parts Clay 90 parts or more are mixed uniformly and finely pulverized to obtain a powder of 10% active ingredient.
  • Formulation Example 4 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part or more is pulverized and mixed well, and after adding water and kneading well, granulation drying As a result, granules containing 5% of the active ingredient are obtained.
  • Formulation Example 5 Suspension 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 or more are mixed and the particle size is 3 microns or less The suspension is wet-pulverized until a suspension of 10% active ingredient is obtained.
  • Granule wettable powder 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 or more uniformly mixed After finely pulverizing, add an appropriate amount of water and knead to make clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.
  • test (Test Example 1) Apple black spot disease control test An emulsion of the compound of the present invention shown below was sprayed at a concentration of 100 ppm active ingredient on apple seedlings (variety “Kokumitsu”, 3-4 leaf stage) cultivated in an unglazed pot. After natural drying at room temperature, conidia spores of Venturia inaequalis were inoculated and kept in a room of 20 ° C. and high humidity for 2 weeks, repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
  • Compound numbers (corresponding to the compound numbers in Tables 1 to 3): A2-1, A2-12, A2-13, A2-14, A2-15, A2-16, A2-20, A2-23, A2-30 A3-1, A3-2, A3-3, A3-5, A3-6, A3-7, A3-8, A3-9, A3-10, A3-12, A3-13, A3-19 (mix ), A3-19 (iso), A3-20, A3-21, A3-22, A3-23, A3-24, A3-26, A3-27, A3-28, A3-29, A3-30, A3 -31, A3-32, A3-33, A3-34, A3-35, A3-36, A3-37 (mix), A3-37 (iso), A3-42, A3-43, A3-44, A3 -45, A3-46, A3-47, A3-49, A3-50
  • Compound numbers (corresponding to the compound numbers in Tables 1 to 3): A2-30, A3-19 (mix), A3-19 (iso), A3-20, A3-21, A3-22, A3-26, A3 -28, A3-32, A3-33, A3-34, A3-35, A3-37 (mix), A3-37 (iso), A3-43, A3-50, A3-59
  • the agricultural and horticultural fungicide comprising the nitrogen-containing heterocyclic compound and / or salt thereof of the present invention as an active ingredient has an excellent control effect, does not cause phytotoxicity to plants, and is toxic to human livestock and to the environment. This is industrially useful.

Abstract

A nitrogenated heterocyclic compound represented by formula (I) [wherein X represents a C1-12 alkyl group which may have a substituent, or the like, and m represents an integer of 0 to 6, provided that, when m represents an integer of 2 or greater, X's may be the same as or different from each other; R represents a C1-12 alkyl group which may have a substituent, or the like; Q represents a C6-12 aryl group which may have a substituent, or the like; A's independently represent a carbon atom or the like; n represents an integer of 1 or 2; and the double line formed by a solid line and a dashed line represents a single bond or a double bond], and a salt thereof.

Description

含窒素ヘテロ環化合物およびその塩並びに農園芸用殺菌剤Nitrogen-containing heterocyclic compounds and salts thereof, and agricultural and horticultural fungicides
　本発明は、新規な含窒素ヘテロ環化合物及びその塩、並びにこれらの化合物の少なくとも１種を有効成分として含有する農園芸用殺菌剤に関する。
　本願は、２００８年９月８日に、日本に出願された特願２００８－２３０２５３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 novel nitrogen-containing heterocyclic compound and a salt thereof, and an agricultural and horticultural fungicide containing at least one of these compounds as an active ingredient.
This application claims priority based on Japanese Patent Application No. 2008-230253 filed in Japan on September 8, 2008, the contents of which are incorporated herein by reference.
　農園芸作物の栽培に当り、作物の病害に対して多数の防除薬剤が使用されているが、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、また植物体に薬害や汚染を生じたり、あるいは人畜魚類に対する毒性や環境への影響の観点から、必ずしも満足すべき防除薬とは言い難いものが少なくない。従って、かかる欠点の少ない安全に使用できる薬剤の出現が強く要請されている。 In the cultivation of agricultural and horticultural crops, many control agents are used against crop diseases, but their control efficacy is insufficient, their use is restricted by the emergence of drug-resistant pathogens, and From the viewpoints of causing phytotoxicity and pollution to plants, or toxicity to human and livestock fish and impact on the environment, there are many things that are not necessarily satisfactory control agents. Accordingly, there is a strong demand for the emergence of such a drug that can be safely used with few defects.
　本発明に関連して、特許文献１、２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、及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。しかしながら、本発明化合物は記載されていない。 In connection with the present invention, Patent Documents 1 and 2 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. However, the compounds of the present invention are not described.
ＷＯ２００５／０７０９１７号パンフレットWO2005 / 0700917 pamphlet ＷＯ２００７／０１１０２２号パンフレットWO2007 / 011022 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の有効成分となりうる、新規含窒素ヘテロ環化合物及びその塩、並びにこれらの化合物の少なくとも１種を有効成分として含有する農園芸用殺菌剤を提供することを課題とする。 The present invention relates to a novel nitrogen-containing heterocyclic compound and a salt thereof, which can be an active ingredient of an agricultural and horticultural fungicide that is reliable and can be used safely, and contains at least one of these compounds as an active ingredient. It is an object to provide a disinfectant.
　上記課題を解決すべく、本発明は下記式（Ｉ）で表される含窒素ヘテロ環化合物又はその塩を提供する。 In order to solve the above problems, the present invention provides a nitrogen-containing heterocyclic compound represented by the following formula (I) or a salt thereof.
式（Ｉ）
Figure JPOXMLDOC01-appb-C000001
 Formula (I)
Figure JPOXMLDOC01-appb-C000001
（式中、Ｘは、置換基を有してもよいＣ１～１２アルキル基、置換基を有してもよいＣ２～１２アルケニル基、置換基を有してもよいＣ２～１２アルキニル基、置換基を有してもよいＣ３～１２シクロアルキル基、置換基を有してもよいＣ４～１２シクロアルケニル基、置換基を有してもよいＣ８～１２シクロアルキニル基、置換基を有してもよいヘテロ環基、置換基を有してもよいＣ１～１２アシル基、置換基を有してもよい（１－イミノ）Ｃ１～１２アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、又はニトロ基を示す。
　ｍは、０～６のいずれかの整数を示す。ｍが２以上のとき、Ｘは互いに同一でも異なっていてもよい。
　隣接する原子上に置換されたＸは、一緒になって、置換基を有してもよい５～８員環を形成してもよい。
　Ｒは、置換基を有してもよいＣ１～１２アルキル基、置換基を有してもよいＣ２～１２アルケニル基、置換基を有してもよいＣ２～１２アルキニル基、置換基を有してもよいＣ３～１２シクロアルキル基、置換基を有してもよいＣ４～１２シクロアルケニル基、置換基を有してもよいＣ８～１２シクロアルキニル基、置換基を有してもよいＣ６～１２アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいＣ１～１２アシル基、又は置換基を有するスルホニル基を示す。
　Ｑは、置換基を有してもよいＣ６～１２アリール基、又は置換基を有してもよいヘテロ環基を示す。
　Ａは、夫々独立して、炭素原子、窒素原子、酸素原子又は硫黄原子を示し、ｎは、１又は２の整数を示す。実線と点線の二重線は単結合又は２重結合を示す。）
で表される含窒素ヘテロ環化合物又はその塩。 Wherein X is a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, a C2-12 alkynyl group which may have a substituent, a substituted A C3-12 cycloalkyl group which may have a group, a C4-12 cycloalkenyl group which may have a substituent, a C8-12 cycloalkynyl group which may have a substituent, and a substituent. An optionally substituted heterocyclic group, an optionally substituted C1-12 acyl group, an optionally substituted (1-imino) C1-12 alkyl group, an optionally substituted hydroxyl group, a substituted An amino group which may have a group, a mercapto group which may have a substituent, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
m represents an integer of 0 to 6. When m is 2 or more, Xs may be the same or different from each other.
X substituted on adjacent atoms may be taken together to form a 5- to 8-membered ring which may have a substituent.
R has a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, a C2-12 alkynyl group which may have a substituent, and a substituent. An optionally substituted C3-12 cycloalkyl group, an optionally substituted C4-12 cycloalkenyl group, an optionally substituted C8-12 cycloalkynyl group, an optionally substituted C6-12 12 represents an aryl group, an optionally substituted heterocyclic group, an optionally substituted C1-12 acyl group, or a substituted sulfonyl group.
Q represents a C6-12 aryl group which may have a substituent, or a heterocyclic group which may have a substituent.
A independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and n represents an integer of 1 or 2. A solid line and a dotted double line indicate a single bond or a double bond. )
Or a salt thereof.
　本発明の含窒素ヘテロ環化合物及びその塩においては、Ａが、炭素原子であり、ｎが２であり、二重結合を介して不飽和の環を形成している、次式（ＩＩ）の化合物又はその塩が好ましい。
Figure JPOXMLDOC01-appb-C000002
 In the nitrogen-containing heterocyclic compound and the salt thereof of the present invention, A is a carbon atom, n is 2, and an unsaturated ring is formed through a double bond. A compound or a salt thereof is preferred.
Figure JPOXMLDOC01-appb-C000002
（式中、Ｘ、ｍ、Ｒ及びＱは、前記と同様の意味を示す。） (Wherein X, m, R and Q have the same meaning as described above.)
　本発明の含窒素ヘテロ環化合物及びその塩においては、さらにＱが、ベンゼン環である次式（ＩＩＩ）の化合物又はその塩がより好ましい。
Figure JPOXMLDOC01-appb-C000003
 In the nitrogen-containing heterocyclic compound and the salt thereof of the present invention, a compound of the following formula (III) or a salt thereof in which Q is a benzene ring is more preferable.
Figure JPOXMLDOC01-appb-C000003
（式中、Ｘ、ｍ及びＲは、前記と同様の意味を示す。
　Ｘ’は、夫々独立して、置換基を有してもよいＣ１～１２アルキル基、置換基を有してもよいＣ２～１２アルケニル基、置換基を有してもよいＣ２～１２アルキニル基、置換基を有してもよいＣ３～１２シクロアルキル基、置換基を有してもよいＣ４～１２シクロアルケニル基、置換基を有してもよいＣ８～１２シクロアルキニル基、置換基を有してもよいＣ６～１２アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいＣ１～１２アシル基、置換基を有してもよい（１－イミノ）Ｃ１～１２アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、又はニトロ基を示す。
　ｓは、０～５のいずれかの整数を示す。ｓが２以上のとき、Ｘ’は互いに同一でも異なっていてもよい。
　隣接する原子上に置換されたＸ’は、一緒になって、置換基を有してもよい５～８員環を形成してもよい。）
　本発明はまた、本発明の化合物又はその塩の少なくとも１種を有効成分として含有する農園芸用殺菌剤を提供する。 (In the formula, X, m and R have the same meaning as described above.
X ′ is independently a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, or a C2-12 alkynyl group which may have a substituent. A C3-12 cycloalkyl group which may have a substituent, a C4-12 cycloalkenyl group which may have a substituent, a C8-12 cycloalkynyl group which may have a substituent, and a substituent. An optionally substituted C6-12 aryl group, an optionally substituted heterocyclic group, an optionally substituted C1-12 acyl group, an optionally substituted (1-imino) C1 ~ 12 alkyl group, hydroxyl group optionally having substituent, amino group optionally having substituent, mercapto group optionally having substituent, sulfonyl group having substituent, halogeno group, cyano group, Or a nitro group is shown.
s represents an integer of 0 to 5. When s is 2 or more, X ′ may be the same as or different from each other.
X ′ substituted on adjacent atoms may be taken together to form a 5- to 8-membered ring which may have a substituent. )
The present invention also provides an agricultural and horticultural fungicide containing as an active ingredient at least one compound of the present invention or a salt thereof.
　本発明の含窒素ヘテロ環化合物及びその塩は新規化合物であり、効果が確実で安全に使用できる農園芸用殺菌剤の有効成分として有用である。
　本発明の農園芸用殺菌剤は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薬剤である。 The nitrogen-containing heterocyclic compounds and salts thereof of the present invention are novel compounds and are useful as active ingredients of agricultural and horticultural fungicides that can be used safely and reliably.
The agricultural and horticultural fungicide of the present invention is an agent that has an excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to human and livestock fish and environmental impact.
　以下、本発明を、１）式（Ｉ）～（ＩＩＩ）で表される含窒素ヘテロ環化合物又はその塩、及び、２）農園芸用殺菌剤に項分けして詳細に説明する。
１）式（Ｉ）～（ＩＩＩ）で表される含窒素ヘテロ環化合物又はその塩
　本発明の化合物は、前記式（Ｉ）～（ＩＩＩ）で表される含窒素ヘテロ環化合物又はその塩である。本発明化合物又はその塩には、水和物、各種溶媒和物や結晶多形等も含まれる。また、本発明化合物は、不斉炭素原子、２重結合などに基づく立体異性体及びそれらの混合物を包含する。 Hereinafter, the present invention will be described in detail by dividing into 1) nitrogen-containing heterocyclic compounds represented by formulas (I) to (III) or salts thereof, and 2) agricultural and horticultural fungicides.
1) Nitrogen-containing heterocyclic compound represented by the formulas (I) to (III) or a salt thereof The compound of the present invention is a nitrogen-containing heterocyclic compound represented by the formula (I) to (III) or a salt thereof. is there. The compound of the present invention or a salt thereof includes hydrates, various solvates and crystal polymorphs. The compounds of the present invention include stereoisomers based on asymmetric carbon atoms, double bonds, and the like, and mixtures thereof.
　式（Ｉ）～（ＩＩＩ）において、
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アルキル基」の「Ｃ１～１２アルキル基」とは、直鎖、又は分岐鎖の炭素数１～１２のアルキル基を意味する。例えば、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、ノニル基、ｎ－デシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、イソペンチル基、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、イソヘキシル基、イソノニル基、２－エチルオクチル基、３－エチルオクチル基、２，３－ジメチルオクチル基等が挙げられる。これらのうち、Ｃ１～６アルキル基が好ましい。 In the formulas (I) to (III),
“C1-12 alkyl group” of “optionally substituted C1-12 alkyl group” for R, X and X ′ means a linear or branched alkyl group having 1 to 12 carbon atoms. To do. For example, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, nonyl group, n-decyl group, i-propyl group I-butyl group, s-butyl group, t-butyl group, isopentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, isohexyl group, isononyl group, 2-ethyloctyl group, 3-ethyl Examples include an octyl group and a 2,3-dimethyloctyl group. Of these, C1-6 alkyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ２～１２アルケニル基」の「Ｃ２～１２アルケニル基」は、アルキル基のいずれか１カ所以上に炭素－炭素二重結合を有する炭素数２～１２の直鎖、又は分岐鎖のアルケニル基を意味する。例えば、ビニル基、１－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－デセニル基、９－デセニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基等が挙げられる。これらのうち、Ｃ２～６アルケニル基が好ましい。 The “C2-12 alkenyl group” in the “optionally substituted C2-12 alkenyl group” for R, X and X ′ is a carbon having a carbon-carbon double bond at any one or more positions in the alkyl group. It means a linear or branched alkenyl group having 2 to 12. For example, vinyl group, 1-propenyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 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-octenyl group, 1-decenyl group, 9- Examples include decenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group and the like. Of these, C2-6 alkenyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ２～１２アルキニル基」の「Ｃ２～１２アルキニル基」は、アルキル基のいずれか１カ所以上に炭素－炭素三重結合を有する炭素数２～１２の直鎖、又は分岐鎖のアルキニル基を意味する。例えば、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－ブチニル基等が挙げられる。これらのうち、Ｃ２～６アルキニル基が好ましい。 “C2-12 alkynyl group” of “optionally substituted C2-12 alkynyl group” for R, X and X ′ is the number of carbon atoms having a carbon-carbon triple bond at any one or more positions of the alkyl group. It means 2 to 12 linear or branched alkynyl groups. For example, ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1- Hexynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1,1-dimethyl-2-butynyl group, etc. Is mentioned. Of these, C2-6 alkynyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ３～１２シクロアルキル基」の「Ｃ３～１２シクロアルキル基」は、環状部分を有する炭素数３～１２のアルキル基を意味する。例えば、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、シクロオクチル基等が挙げられる。これらのうち、Ｃ３～６シクロアルキル基が好ましい。 “C3-12 cycloalkyl group” of “optionally substituted C3-12 cycloalkyl group” for R, X and X ′ means an alkyl group having 3-12 carbon atoms having a cyclic portion. For example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like can be given. Of these, C3-6 cycloalkyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ４～１２シクロアルケニル基」の「Ｃ４～１２シクロアルケニル基」は、環状部分を有する炭素数４～１２のアルケニル基を意味する。例えば、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等が挙げられる。これらのうち、Ｃ４～８シクロアルケニル基が好ましい。 “C4-12 cycloalkenyl group” of “optionally substituted C4-12 cycloalkenyl group” for R, X and X ′ means an alkenyl group having 4 to 12 carbon atoms having a cyclic portion. Examples thereof 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. Of these, C4-8 cycloalkenyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ８～１２シクロアルキニル基」の「Ｃ８～１２シクロアルキニル基」は、環状部分を有する炭素数８～１２のアルキニル基を意味する。例えば、５－シクロオクチニル基、６－シクロデシニル基等が挙げられる。 “C8-12 cycloalkynyl group” of “optionally substituted C8-12 cycloalkynyl group” for R, X and X ′ means an alkynyl group having 8-12 carbon atoms having a cyclic portion. For example, 5-cyclooctynyl group, 6-cyclodecynyl group and the like can be mentioned.
　Ｒ、Ｑ、及びＸ’の「置換基を有してもよいＣ６～１２アリール基」の「Ｃ６～１２アリール基」は、単環又は多環の炭素数６～１２のアリール基を意味する。ここで、多環アリール基の場合は、完全不飽和に加え、部分飽和の基も包含する。例えばフェニル基、ナフチル基、アズレニル基、インデニル基、インダニル基、テトラリニル基等が挙げられる。これらのうち、フェニル基が好ましい。 The “C6-12 aryl group” in the “optionally substituted C6-12 aryl group” for R, Q, and X ′ means a monocyclic or polycyclic aryl group having 6 to 12 carbon atoms. . Here, in the case of a polycyclic aryl group, a partially saturated group is included in addition to the fully unsaturated group. Examples thereof include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group. Of these, a phenyl group is preferred.
　Ｒ、Ｑ、Ｘ及びＸ’の「置換基を有してもよいヘテロ環基」の「ヘテロ環基」は、環を構成する原子として炭素原子以外に窒素原子、酸素原子及び硫黄原子から選ばれる１乃至４個の複素原子を含む５乃至７員の芳香族ヘテロ環、飽和ヘテロ環、不飽和ヘテロ環又はこれらのヘテロ環とベンゼン環が縮合した縮合ヘテロ環を意味する。例えば、フラン－２－イル基、フラン－３－イル基、チオフェン－２－イル基、チオフェン－３－イル基、ピロ－ル－１－イル基、ピロ－ル－２－イル基、ピロ－ル－３－イル基、ピリジン－２－イル基、ピリジン－３－イル基、ピリジン－４－イル基、ピラジン－２－イル基、ピラジン－３－イル基、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、ピリダジン－３－イル基、ピリダジン－４－イル基、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、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、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、ピペラジン－１－イル基、ピペラジン－２－イル基、ピペラジン－３－イル基、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、１，３－ベンゾジオキソール－４－イル基、１，３－ベンゾジオキソール－５－イル基、１，４－ベンゾジオキサン－５－イル基、１，４－ベンゾジオキサン－６－イル基、３，４－ジヒドロ－２Ｈ－１，５－ベンゾジオキセピン－６－イル基、３，４－ジヒドロ－２Ｈ－１，５－ベンゾジオキセピン－７－イル基、２，３－ジヒドロベンゾフラン－４－イル基、２，３－ジヒドロベンゾフラン－５－イル基、２，３－ジヒドロベンゾフラン－６－イル基、２，３－ジヒドロベンゾフラン－７－イル基、ベンゾフラン－２－イル基、ベンゾフラン－３－イル基、ベンゾフラン－４－イル基、ベンゾフラン－５－イル基、ベンゾフラン－６－イル基、ベンゾフラン－７－イル基、ベンゾチオフェン－２－イル基、ベンゾチオフェン－３－イル基、ベンゾチオフェン－４－イル基、ベンゾチオフェン－５－イル基、ベンゾチオフェン－６－イル基、ベンゾチオフェン－７－イル基、キノキサリン－２－イル基、キノキサリン－５－イル基、キノキサリン－６－イル基、インドール－１－イル基、インドール－２－イル基、インドール－３－イル基、インドール－４－イル基、インドール－５－イル基、インドール－６－イル基、インドール－７－イル基、イソインドール－１－イル基、イソインドール－２－イル基、イソインドール－４－イル基、イソインドール－５－イル基、イソインドール－６－イル基、イソインドール－７－イル基、イソベンゾフラン－１－イル基、イソベンゾフラン－４－イル基、イソベンゾフラン－５－イル基、イソベンゾフラン－６－イル基、イソベンゾフラン－７－イル基、クロメン－２－イル基、クロメン－３－イル基、クロメン－４－イル基、クロメン－５－イル基、クロメン－６－イル基、クロメン－７－イル基、クロメン－８－イル基、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、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、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、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、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、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、ベンゾイミダゾール－１－イル基、ベンゾイミダゾール－２－イル基、ベンゾイミダゾール－４－イル基、ベンゾイミダゾール－５－イル基、ベンゾチアゾール－２－イル基、ベンゾチアゾール－４－イル基、ベンゾチアゾール－５－イル基、ベンゾオキサゾール－２－イル基、ベンゾオキサゾール－４－イル基、ベンゾオキサゾール－５－イル基、キノリン－２－イル基、キノリン－３－イル基、キノリン－４－イル基、キノリン－５－イル基、キノリン－６－イル基、キノリン－７－イル基、キノリン－８－イル基、イソキノリン－１－イル基、イソキノリン－３－イル基、イソキノリン－４－イル基、イソキノリン－５－イル基、イソキノリン－６－イル基、イソキノリン－７－イル基、イソキノリン－８－イル基、１，３，４－チアジアゾール－２－イル基、１，２，４－チアジアゾール－３－イル基、１，３，４－オキサジアゾール－２－イル基、１，２，４－オキサジアゾール－３－イル基、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、テトラゾール－１－イル基、テトラゾール－２－イル基等が挙げられる。
　これらのうち、５～１０員のヘテロ環基が好ましい。 The “heterocyclic group” of the “optionally substituted heterocyclic group” for R, Q, X and X ′ is selected from a nitrogen atom, an oxygen atom and a sulfur atom in addition to a carbon atom as a ring-constituting atom. Or a 5- to 7-membered aromatic heterocycle containing 1 to 4 heteroatoms, a saturated heterocycle, an unsaturated heterocycle, or a fused heterocycle obtained by condensing these heterocycles with a benzene ring. For example, furan-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-yl group, pyrrol-1-yl group, pyrrol-2-yl group, pyro- Ru-3-yl group, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group, pyrazin-2-yl group, pyrazin-3-yl group, pyrimidin-2-yl group, pyrimidine -4-yl group, pyrimidin-5-yl group, pyridazin-3-yl group, pyridazin-4-yl group, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group, pyrrolidin-1-yl group, pyrrolidin- 2-yl group, pyrrolidin-3-yl group, piperidin-1-yl group, piperidin-2-yl group, piperidin-3-yl group, piperidin-4-yl group, piperazin-1-yl group, piperazine-2 -I Group, piperazin-3-yl group, morpholin-2-yl group, morpholin-3-yl group, morpholin-4-yl group, 1,3-benzodioxol-4-yl group, 1,3-benzodio Xol-5-yl group, 1,4-benzodioxan-5-yl group, 1,4-benzodioxan-6-yl group, 3,4-dihydro-2H-1,5-benzodioxepin-6 -Yl group, 3,4-dihydro-2H-1,5-benzodioxepin-7-yl group, 2,3-dihydrobenzofuran-4-yl group, 2,3-dihydrobenzofuran-5-yl group, 2,3-dihydrobenzofuran-6-yl group, 2,3-dihydrobenzofuran-7-yl group, benzofuran-2-yl group, benzofuran-3-yl group, benzofuran-4-yl group, benzofuran-5-yl group Group, benzof N-6-yl group, benzofuran-7-yl group, benzothiophen-2-yl group, benzothiophen-3-yl group, benzothiophen-4-yl group, benzothiophen-5-yl group, benzothiophen-6 -Yl group, benzothiophen-7-yl group, quinoxalin-2-yl group, quinoxalin-5-yl group, quinoxalin-6-yl group, indol-1-yl group, indol-2-yl group, indole-3 -Yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, isoindol-1-yl, isoindol-2-yl, isoindole -4-yl group, isoindol-5-yl group, isoindol-6-yl group, isoindol-7-yl group, isobenzofuran-1-yl group, Isobenzofuran-4-yl group, isobenzofuran-5-yl group, isobenzofuran-6-yl group, isobenzofuran-7-yl group, chromen-2-yl group, chromen-3-yl group, chromene-4- Yl, chromen-5-yl, chromen-6-yl, chromen-7-yl, chromen-8-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl Group, imidazol-5-yl group, pyrazol-1-yl group, pyrazol-3-yl group, pyrazol-4-yl group, pyrazol-5-yl group, thiazol-2-yl group, thiazol-4-yl group , Thiazol-5-yl group, oxazol-2-yl group, oxazol-4-yl group, oxazol-5-yl group, isothiazol-3-yl group, isothiazole 4-yl group, isothiazol-5-yl group, isoxazol-3-yl group, isoxazol-4-yl group, isoxazol-5-yl group, benzimidazol-1-yl group, benzimidazol-2- Yl group, benzoimidazol-4-yl group, benzimidazol-5-yl group, benzothiazol-2-yl group, benzothiazol-4-yl group, benzothiazol-5-yl group, benzoxazol-2-yl group Benzoxazol-4-yl group, benzoxazol-5-yl group, quinolin-2-yl group, quinolin-3-yl group, quinolin-4-yl group, quinolin-5-yl group, quinolin-6-yl Group, quinolin-7-yl group, quinolin-8-yl group, isoquinolin-1-yl group, isoquinolin-3-yl group, isoquinoline- -Yl group, isoquinolin-5-yl group, isoquinolin-6-yl group, isoquinolin-7-yl group, isoquinolin-8-yl group, 1,3,4-thiadiazol-2-yl group, 1,2,4 -Thiadiazol-3-yl group, 1,3,4-oxadiazol-2-yl group, 1,2,4-oxadiazol-3-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, tetrazol-1-yl group, tetrazol-2-yl group and the like.
Of these, 5- to 10-membered heterocyclic groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してよいＣ１～１２アシル基」の「Ｃ１～１２アシル基」は、水素原子、直鎖若しくは分岐鎖のＣ１～１１のアルキル基、直鎖若しくは分岐鎖のＣ２～１１のアルケニル基、直鎖若しくは分岐鎖のＣ２～１１のアルキニル基、単環又は多環のＣ６～１０のアリール基、又は、環を構成する原子として炭素原子以外に窒素原子、酸素原子及び硫黄原子から選ばれる１乃至４個の複素原子を含む５乃至７員のヘテロ環基が、カルボニル基と結合した基を意味する。
　例えば、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、ノナノイル基、デカノイル基、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、３－メチルノナノイル基、８－メチルノナノイル基、３－エチルオクタノイル基等のアルキルカルボニル基；アクリロイル基、メタクリロイル基等のアルケニルカルボニル基；プロピオロイル基等のアルキニルカルボニル基；ベンゾイル基、ナフチルカルボニル基、ビフェニルカルボニル基、アントラニルカルボニル基等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等のヘテロ環カルボニル基等が挙げられる。これらのうち、Ｃ１～７アシル基が好ましい。 “C1-12 acyl group” of “optionally substituted C1-12 acyl group” for R, X and X ′ is a hydrogen atom, a linear or branched C1-11 alkyl group, linear or Branched C2-11 alkenyl group, straight chain or branched C2-11 alkynyl group, monocyclic or polycyclic C6-10 aryl group, or nitrogen atom other than carbon atoms as atoms constituting the ring And a 5- to 7-membered heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom and a sulfur atom means a group bonded to a carbonyl group.
For example, formyl group, acetyl group, propionyl group, n-propylcarbonyl group, n-butylcarbonyl group, pentanoyl group, valeryl group, octanoyl group, nonanoyl group, decanoyl group, i-propylcarbonyl group, i-butylcarbonyl group, Alkylcarbonyl groups such as pivaloyl group, isovaleryl group, 3-methylnonanoyl group, 8-methylnonanoyl group, 3-ethyloctanoyl group; alkenylcarbonyl groups such as acryloyl group, methacryloyl group; alkynylcarbonyl groups such as propioroyl group; benzoyl group, Examples thereof include arylcarbonyl groups such as naphthylcarbonyl group, biphenylcarbonyl group and anthranylcarbonyl group; heterocyclic carbonyl groups such as 2-pyridylcarbonyl group and thienylcarbonyl group. Of these, C1-7 acyl groups are preferred.
　Ｘ及びＸ’の「置換基を有してもよい（１－イミノ）Ｃ１～１２アルキル基」の「（１－イミノ）Ｃ１～１２アルキル基」は、直鎖又は分岐鎖のＣ１～１１のアルキル基が、イミノメチル基と結合した基を意味する。例えば、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、（１－イミノ）オクチルイミノ基、（１－イミノ）イソブチル基、（１－イミノ）イソペンチル基、（１－イミノ）ネオペンチル基等が挙げられる。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) C1-12 alkyl group” in the “optionally substituted (1-imino) C1-12 alkyl group” of X and X ′ is a linear or branched C1-11 An alkyl group means a group bonded to an iminomethyl group. For example, iminomethyl group, (1-imino) ethyl group, (1-imino) propyl group, (1-imino) butyl group, (1-imino) pentyl group, (1-imino) hexyl group, (1-imino) Examples include heptyl group, (1-imino) octylimino group, (1-imino) isobutyl group, (1-imino) isopentyl group, (1-imino) neopentyl group and the like. Of these, (1-imino) C1-6 alkyl groups are preferred.
　Ｘ及びＸ’の「ハロゲノ基」としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられる。 Examples of the “halogeno group” for X and X ′ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
（「置換基を有する」又は「置換基を有してもよい」の説明）
　本明細書において、「置換基を有する」又は「置換基を有してもよい」とは、上記のそれぞれの「基」のいずれかの水素原子と、「置換基」が置換していること、又は置換していてもよいことをいう。「置換基」としては、例えば上記のそれぞれの「基」を挙げることができるが、それら「置換基」はさらに「別の基」で置換された「置換基」であってもよい。「別の基」としては、例えば上記のそれぞれの「基」を挙げることができる。
　以下に、上記のそれぞれの「基」において、上記のいずれかの「基」により置換された例を示す。 (Description of “having a substituent” or “may have a substituent”)
In the present specification, "having a substituent" or "may have a substituent" means that any hydrogen atom in each of the above "groups" is substituted with the "substituent". Or it may be substituted. Examples of the “substituent” include the above-mentioned “groups”, but the “substituent” may be a “substituent” further substituted with “another group”. Examples of “another group” include the above-mentioned “groups”.
Examples in which each of the above “groups” is substituted with any of the above “groups” are shown below.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アルキル基」において、「置換基を有してもよいＣ３～１２シクロアルキル基」により置換された「Ｃ１～１２アルキル基」としては、例えば、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、２－シクロオクチルエチル基等が挙げられる。これらのうち、Ｃ４～１０シクロアルキルＣ１～６アルキル基が好ましい。 The “C1-12 alkyl group” substituted by the “optionally substituted C3-12 cycloalkyl group” in the “optionally substituted C1-12 alkyl group” of R, X and X ′ Examples of "" include a cyclopropylmethyl group, a 2-cyclopropylethyl group, a cyclopentylmethyl group, a 2-cyclohexylethyl group, a 2-cyclooctylethyl group, and the like. Of these, C4-10 cycloalkyl C1-6 alkyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アルキル基」において、「置換基を有してもよいＣ４～１２シクロアルケニル基」により置換された「Ｃ１～１２アルキル基」としては、例えば、シクロペンテニルメチル基、３－シクロペンタテニルメチル基、３－シクロヘキセニルメチル基、２－（３－シクロヘキセニル）エチル基等が挙げられる。これらのうち、Ｃ４～８シクロアルケニルＣ１～６アルキル基が好ましい。 The “C1-12 alkyl group” substituted by the “optionally substituted C4-12 cycloalkenyl group” in the “optionally substituted C1-12 alkyl group” of R, X and X ′ Examples of “include cyclopentenylmethyl, 3-cyclopentenylmethyl, 3-cyclohexenylmethyl, 2- (3-cyclohexenyl) ethyl and the like. Of these, C4-8 cycloalkenyl C1-6 alkyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アルキル基」において、「置換基を有してもよいＣ８～１２シクロアルキニル基」により置換された「Ｃ１～１２アルキル基」としては、例えば、５－シクロオクチニルメチル基等が挙げられる。これらのうち、Ｃ８～１０シクロアルキニルＣ１～６アルキル基が好ましい。 The “C1-12 alkyl group” substituted by the “optionally substituted C8-12 cycloalkynyl group” in the “optionally substituted C1-12 alkyl group” of R, X and X ′ "Includes, for example, a 5-cyclooctynylmethyl group and the like. Of these, C8-10 cycloalkynyl C1-6 alkyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アルキル基」において、「ハロゲノ基」により置換された「Ｃ１～１２アルキル基」としては、例えば、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、２，２，４，４，６，６－ヘキサクロロ－３－プロピル－オクチル基等が挙げられる。これらのうち、ハロゲン原子が１～３個置換したＣ１～６アルキル基が好ましい。 In the “optionally substituted C1-12 alkyl group” for R, X and X ′, the “C1-12 alkyl group” substituted by the “halogeno group” includes, for example, a fluoromethyl group, a chloromethyl group, and the like. Group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl 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, Ruorodeshiru group, hexa-chloro octyl into 2,2,4,4,6,6, 2,2,4,4,6,6-hexachloro-3-propyl - octyl group. Of these, C1-6 alkyl groups substituted with 1 to 3 halogen atoms are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アルキル基」において、「置換基を有してもよいＣ６～１２アリール基」により置換された「Ｃ１～１２アルキル基」としては、例えば、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－ナフチルメチル基等が挙げられる。これらのうち、Ｃ６～１２アリールＣ１～６アルキル基が好ましい。 “C1-12 alkyl group” substituted by “optionally substituted C6-12 aryl group” in “optionally substituted C1-12 alkyl group” for R, X and X ′ Examples thereof include benzyl group, phenethyl group, 3-phenylpropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group and the like. Of these, C6-12 aryl C1-6 alkyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アルキル基」において、「置換基を有してもよいヘテロ環基」により置換された「Ｃ１～１２アルキル基」としては、例えば、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－ピラジルメチル基、３－ピラジルメチル基、２－（２－ピラジル）エチル基、２－（３－ピラジル）エチル基、３－（２－ピラジル）プロピル基、３－（３－ピラジル）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）プロピル基等が挙げられる。これらのうち、５～１０員ヘテロ環Ｃ１～６アルキル基が好ましい。 In the “optionally substituted C1-12 alkyl group” of R, X and X ′, the “C1-12 alkyl group” substituted by the “optionally substituted heterocyclic group” For example, 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-pyrazylmethyl group, 3-pyrazylmethyl group, 2- (2-pyrazyl) ethyl group 2- (3-pyrazyl) ethyl group, 3- (2-pyrazyl) propyl group, 3- (3-pyrazyl) 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) ethyl group, Examples include 2- (3-furyl) ethyl group, 3- (2-furyl) propyl group, 3- (3-furyl) propyl group and the like. Of these, a 5- to 10-membered heterocyclic C1-6 alkyl group is preferable.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アルキル基」において、「水酸基」により置換された「Ｃ１～１２アルキル基」としては、すなわち、「置換基を有してもよいヒドロキシＣ１～１２アルキル基」であり、例えば、ヒドロキシメチル基、ヒドロキシエチル基、ヒドロキシプロピル基等が挙げられる。これらのうち、ヒドロキシＣ１～６アルキル基が好ましい。 In the “optionally substituted C1-12 alkyl group” for R, X and X ′, the “C1-12 alkyl group” substituted by the “hydroxyl group” means that “having a substituent” A hydroxy C1-12 alkyl group ”, and examples thereof include a hydroxymethyl group, a hydroxyethyl group, and a hydroxypropyl group. Of these, hydroxy C1-6 alkyl groups are preferred.
　さらに、「置換基を有してもよいヒドロキシＣ１～１２アルキル基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「ヒドロキシＣ１～１２アルキル基」としては、例えば、メトキシメチル基、エトキシメチル基、メトキシエチル基、エトキシエチル基、メトキシｎ－プロピル基、エトキシメチル基、エトキシエチル基、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－ブトキシエチル基等が挙げられる。これらのうち、Ｃ１～６アルコキシＣ１～６アルキル基が好ましい。 Furthermore, in the “hydroxy C1-12 alkyl group optionally having substituent”, the “hydroxy C1-12 alkyl group” substituted by “C1-12 alkyl group optionally having substituent” includes: For example, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, Examples thereof include a t-butoxyethyl group. Of these, C1-6 alkoxy C1-6 alkyl groups are preferred.
　また、「置換基を有してもよいヒドロキシＣ１～１２アルキル基」において、「置換基を有してもよいＣ１～１２アシル基」により置換された「ヒドロキシＣ１～１２アルキル基」としては、例えば、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等が挙げられる。これらのうち、Ｃ２～７アシルオキシＣ１～６アルキル基が好ましい。 In addition, in the “hydroxy C1-12 alkyl group optionally having substituent”, the “hydroxy C1-12 alkyl group” substituted by “C1-12 acyl group optionally having substituent” Examples include formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group and the like. Of these, C2-7 acyloxy C1-6 alkyl groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ３～１２シクロアルキル基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「Ｃ３～１２シクロアルキル基」としては、例えば、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等が挙げられる。これらのうち、Ｃ１～６アルキルが１～３個置換したＣ４～１０シクロアルキル基が好ましい。 "C3-12 cycloalkyl" substituted by "optionally substituted C1-12 alkyl group" in "optionally substituted C3-12 cycloalkyl group" for R, X and X ' Examples of the “group” include 2,3,3-trimethylcyclobutyl group, 4,4,6,6-tetramethylcyclohexyl group, 1,3-dibutylcyclohexyl group and the like. Of these, C4-10 cycloalkyl groups in which 1 to 3 C1-6 alkyls are substituted are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ４～１２シクロアルケニル基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「Ｃ４～１２シクロアルケニル基」としては、例えば、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等が挙げられる。これらのうち、Ｃ１～６アルキルが１～３個置換したＣ５～９シクロアルケニル基が好ましい。 “C4-12 cycloalkenyl group” substituted by “optionally substituted C1-12 alkyl group” in “optionally substituted C4-12 cycloalkenyl group” for R, X and X ′ Examples of the “group” include 2-methyl-3-cyclohexenyl group, 3,4-dimethyl-3-cyclohexenyl group and the like. Of these, a C5-9 cycloalkenyl group in which 1 to 3 C1-6 alkyl is substituted is preferable.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ８～１２シクロアルキニル基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「Ｃ８～１２シクロアルキニル基」としては、例えば、２，３－ジエチル－４－シクロデシニル基等が挙げられる。これらのうち、Ｃ１～６アルキルが１～３個置換したＣ８～１０シクロアルキニル基が好ましい。 “C8-12 cycloalkynyl” substituted by “optionally substituted C1-12 alkyl group” in “optionally substituted C8-12 cycloalkynyl group” of R, X and X ′ Examples of the “group” include 2,3-diethyl-4-cyclodecynyl group. Of these, a C8-10 cycloalkynyl group in which 1 to 3 C1-6 alkyl is substituted is preferable.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ２～１２アルケニル基」において、「ハロゲノ基」により置換された「Ｃ２～１２アルケニル基」としては、例えば、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－ヘキセニル基等が挙げられる。これらのうち、ハロゲン原子が１～３個置換したＣ２～６アルケニル基が好ましい。 In the “optionally substituted C2-12 alkenyl group” for R, X and X ′, the “C2-12 alkenyl group” substituted by the “halogeno group” includes, for example, 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 Examples include -2-propenyl group, 3,3-difluoro-2-propenyl group, 2,4,6-trichloro-2-hexenyl group, and the like. Of these, C2-6 alkenyl groups substituted with 1 to 3 halogen atoms are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ２～１２アルキニル基」において、「ハロゲノ基」により置換された「Ｃ２～１２アルキニル基」としては、例えば、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、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－ブチニル基等が挙げられる。これらのうち、ハロゲン原子が１～３個置換したＣ２～６アルキニル基が好ましい。 In the “optionally substituted C2-12 alkynyl group” for R, X and X ′, the “C2-12 alkynyl group” substituted by the “halogeno group” includes, for example, 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, 5, Examples include a 5-dichloro-2-methyl-3-pentynyl group, a 4-chloro-1,1-dimethyl-2-butynyl group, and the like. Of these, C2-6 alkynyl groups substituted with 1 to 3 halogen atoms are preferred.
　Ｘ及びＸ’の「置換基を有してもよい水酸基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「水酸基」としては、すなわち、「置換基を有してもよいＣ１～１２アルコキシ基」であり、例えば、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、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、イソヘキシルオキシ基、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－エチルブトキシ基等が挙げられ、さらに「置換基を有してもよいＣ３～１２シクロアルキル基」又は、「置換基を有してもよいＣ６～１２アリール基」により置換された「アルコキシ基」としては、例えば、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、ベンジルオキシ基等が挙げられる。これらのうち、Ｃ１～７アルコキシ基が好ましい。 In the “hydroxyl group optionally having substituent (s)” of X and X ′, the “hydroxyl group” substituted by the “optionally substituted C1-12 alkyl group” means that C1-12 alkoxy group ”, for example, methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, decyloxy group, i-propoxy group I-butoxy group, s-butoxy group, t-butoxy group, 1-ethylpropoxy group, isohexyloxy 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-dimethylbutoxy group Group, 2,3-dimethylbutoxy group, 1-ethylbutoxy group, 2-ethylbutoxy group and the like, and further, “optionally substituted C3-12 cycloalkyl group” or “having a substituent. Examples of the “alkoxy group” substituted by “optionally C6-12 aryl group” include cyclopropylmethyloxy group, 2-cyclopentylethyloxy group, benzyloxy group and the like. Of these, C1-7 alkoxy groups are preferred.
　また、上記「アルコキシ基」が「ハロゲノ基」により置換された「基」としては、例えば、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等が挙げられる。これらのうち、ハロゲン原子が１～３個置換したＣ１～６アルコキシ基が好ましい。 Examples of the “group” in which the “alkoxy group” is substituted with the “halogeno group” include, for example, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1 -Difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group and the like. Of these, C1-6 alkoxy groups substituted with 1 to 3 halogen atoms are preferred.
　Ｘ及びＸ’の「置換基を有してもよい水酸基」において、「置換基を有してもよいＣ２～１２アルケニル基」により置換された「水酸基」としては、すなわち、「置換基を有してもよいＣ２～１２アルケニルオキシ基」であり、例えば、ビニルオキシ基、１－プロペニルオキシ基、２－プロペニルオキシ基、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－ヘプテニルオキシ基、６－ヘプテニルオキシ基、１－オクテニルオキシ基、７－オクテニルオキシ基、１－デセニルオキシ基、９－デセニルオキシ基、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－ブテニルオキシ基等が挙げられる。これらのうち、Ｃ２～６アルケニルオキシ基が好ましい。 In the “hydroxyl group optionally having substituent (s)” of X and X ′, the “hydroxyl group” substituted by “optionally substituted C2-12 alkenyl group” means that A C2-12 alkenyloxy group which may be, for example, vinyloxy group, 1-propenyloxy group, 2-propenyloxy group, 1-butenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-pentenyloxy group. Group, 2-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1-heptenyloxy group, 6-heptenyloxy group, 1-octenyloxy group, 7-octenyloxy group, 1-decenyl Oxy group, 9-decenyloxy group, 1-methyl-2-propenyloxy group, 2-methyl-2-propenyloxy group, 1-methyl-2-butenyloxy group, 2-methyl-2-butenyloxy group and the like. Of these, C2-6 alkenyloxy groups are preferred.
　Ｘ及びＸ’の「置換基を有する水酸基」において、「置換基を有してもよいＣ２～１２アルキニル基」により置換された「水酸基」としては、すなわち、「Ｃ２～１２アルキニルオキシ基」であり、例えば、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、ドデシニルオキシ基、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、４－エチルヘキサデシニルオキシ基等が挙げられる。これらのうち、Ｃ２～６アルキニルオキシ基が好ましい。 In the “hydroxyl group having a substituent” of X and X ′, the “hydroxyl group” substituted by the “optionally substituted C2-12 alkynyl group” means that in the “C2-12 alkynyloxy group” For example, ethynyloxy group, propynyloxy group, propargyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group Group, 4-pentynyloxy group, 1-hexynyloxy group, dodecynyloxy 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, 4-ethylhexadecynyloxy group And the like. Of these, C2-6 alkynyloxy groups are preferred.
　Ｘ及びＸ’の「置換基を有する水酸基」において、「置換基を有してもよいＣ３～１２シクロアルキル基」により置換された「水酸基」としては、すなわち、「Ｃ３～１２シクロアルコキシ基」であり、例えば、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が挙げられ、さらに「置換基を有してもよいＣ１～１２アルキル基」により置換されたシクロアルコキシ基の例としては、例えば、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等が挙げられる。これらのうち、Ｃ３～６シクロアルコキシ基が好ましい。 In the “hydroxyl group having a substituent” in X and X ′, the “hydroxyl group” substituted by the “optionally substituted C3-12 cycloalkyl group” means the “C3-12 cycloalkoxy group”. Examples thereof include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group, and further, “C1-12 alkyl optionally having substituent (s)” Examples of the cycloalkoxy group substituted by “group” include, for example, 2-methylcyclopropyloxy group, 2-ethylcyclopropyloxy group, 2,3,3-trimethylcyclobutyloxy group, 2-methylcyclopentyloxy group 2-ethylcyclohexyloxy group, 2-ethylcyclooctyloxy group, 4 4,6,6-tetramethyl-cyclohexyl group, 1,3-butylcyclohexyl group, and the like. Of these, C3-6 cycloalkoxy groups are preferred.
　Ｘ及びＸ’の「置換基を有する水酸基」において、「置換基を有してもよいＣ６～１２アリール基」により置換された「水酸基」としては、すなわち、「置換基を有してもよいＣ６～１２アリールオキシ基」であり、例えば、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等が挙げられる。これらのうち、Ｃ６～１２アリールオキシ基が好ましい。 In the “hydroxyl group having a substituent” in X and X ′, the “hydroxyl group” substituted by the “optionally substituted C6-12 aryl group”, that is, “may have a substituent” C6-12 aryloxy group ”, for example, phenyloxy group, naphthyloxy group, azulenyloxy group, indenyloxy group, indanyloxy group, tetralinyloxy group and the like. Of these, C6-12 aryloxy groups are preferred.
　Ｘ及びＸ’の「置換基を有する水酸基」において、「置換基を有してもよいＣ１～１２アシル基」により置換された「水酸基」としては、すなわち、「置換基を有してもよいＣ１～１２アシルオキシ基」であり、例えば、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等が挙げられる。これらのうち、Ｃ１～６アシルオキシ基が好ましい。 In the “hydroxyl group having a substituent” of X and X ′, the “hydroxyl group” substituted by the “optionally substituted C1-12 acyl group”, that is, “may have a substituent” C1-12 acyloxy group ", for example, acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group, n-butylcarbonyloxy group, i-butylcarbonyloxy group, pentanoyloxy Group, pivaloyloxy group and the like. Of these, C1-6 acyloxy groups are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アシル基」において、「ハロゲノ基」により置換された「Ｃ１～１２アシル基」としては、例えば、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等が挙げられる。これらのうち、ハロゲン原子が１～３個置換したＣ１～６アシル基が好ましい。 In the “optionally substituted C1-12 acyl group” for R, X and X ′, the “C1-12 acyl group” substituted by the “halogeno group” includes, for example, a monofluoroacetyl group, monochloro Acetyl group, monobromoacetyl group, difluoroacetyl group, dichloroacetyl group, dibromoacetyl group, trifluoroacetyl group, trichloroacetyl group, tribromoacetyl group, 3,3,3-trifluoropropionyl group, 3,3,3 -Trichloropropionyl group, 2,2,3,3,3-pentafluoropropionyl group and the like. Of these, C1-6 acyl groups substituted with 1 to 3 halogen atoms are preferred.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アシル基」において、「置換基を有してもよいＣ２～１２アルケニル基」、「置換基を有してもよいＣ２～１２アルキニル基」、「置換基を有してもよいＣ６～１２アリール基」又は「置換基を有してもよいヘテロ環基」により置換された「Ｃ１～１２アシル基」としては、例えば、３－アリル－フェニルカルボニル基、３－エチニル－フェニルカルボニル基、ベンジルカルボニル基、フェネチルカルボニル基、２－ピリジルメチルカルボニル基等が挙げられる。 In the “optionally substituted C1-12 acyl group” of R, X and X ′, “optionally substituted C2-12 alkenyl group”, “optionally substituted C2 Examples of the “C1-12 acyl group” substituted by “˜12 alkynyl group”, “optionally substituted C6-12 aryl group” or “optionally substituted heterocyclic group” include: , 3-allyl-phenylcarbonyl group, 3-ethynyl-phenylcarbonyl group, benzylcarbonyl group, phenethylcarbonyl group, 2-pyridylmethylcarbonyl group and the like.
　Ｒ、Ｘ及びＸ’の「置換基を有してもよいＣ１～１２アシル基」において、「置換基を有してもよいＣ１アシル基」が「水酸基」により置換された「基」としては、すなわち、「カルボキシル基」である。 In the “optionally substituted C1-12 acyl group” for R, X and X ′, “the C1 acyl group optionally having substituent (s)” is replaced by “hydroxyl group”. That is, it is a “carboxyl group”.
　Ｒ、Ｘ及びＸ’の「置換基を有してよいＣ１～１２アシル基」において、「置換基を有してもよいＣ１アシル基」が「置換基を有する水酸基」により置換された「基」としては、すなわち、「置換基を有するカルボキシル基」である。この「置換基を有するカルボキシル基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「カルボキシル基」としては、例えば、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、デシルオキシカルボニル基等が挙げられる。さらに「置換基を有してもよいＣ３～１２シクロアルキル基」又は、「置換基を有してもよいＣ６～１２アリール基」により置換された「アルキル置換カルボキシル基」としては、例えば、シクロプロピルメチルオキシカルボニル基、２－シクロペンチルエチルオキシカルボニル基、ベンジルオキシカルボニル基等が、挙げられる。これらのうち、Ｃ１～７アルコキシカルボニル基が好ましい。 In the “optionally substituted C1-12 acyl group” of R, X and X ′, “the optionally substituted C1 acyl group” is replaced by “the substituted hydroxyl group” "Is a" carboxyl group having a substituent ". In this “carboxyl group having a substituent”, examples of the “carboxyl group” substituted by the “optionally substituted C1-12 alkyl group” include, for example, a methoxycarbonyl group, an ethoxycarbonyl group, and n-propoxy group. Examples include a carbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, decyloxycarbonyl group and the like. Furthermore, examples of the “alkyl-substituted carboxyl group” substituted by “optionally substituted C3-12 cycloalkyl group” or “optionally substituted C6-12 aryl group” include, for example, cyclo Examples include propylmethyloxycarbonyl group, 2-cyclopentylethyloxycarbonyl group, benzyloxycarbonyl group and the like. Of these, C1-7 alkoxycarbonyl groups are preferred.
　Ｘ及びＸ’の「置換基を有してもよい（１－イミノ）Ｃ１～１２アルキル基」において、イミノメチル基の窒素原子上の水素原子が、「水酸基」により置換された「基」としては、すなわち、「置換基を有してもよい（１－ヒドロキシイミノ）Ｃ１～１２アルキル基」である。例えば、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）ブチル基等が挙げられる。これらのうち、（１－ヒドロキシイミノ）Ｃ１～６アルキル基が好ましい。
　また、「置換基を有してもよい（１－ヒドロキシイミノ）Ｃ１～１２アルキル基」において、水酸基上の水素原子が、「置換基を有してもよいＣ１～１２アルキル基」により置換された「基」としては、例えば、メトキシイミノメチル基、（１－エトキシイミノ）メチル基、（１－エトキシイミノ）エチル基等が挙げられる。これらのうち、（１－（Ｃ１～６アルコキシ）イミノ）Ｃ１～６アルキル基が好ましい。 As the “group” in which the hydrogen atom on the nitrogen atom of the iminomethyl group in the “optionally substituted (1-imino) C1-12 alkyl group” of X and X ′ is replaced by “hydroxyl group”, That is, “an optionally substituted (1-hydroxyimino) C1-12 alkyl group”. Examples thereof include a hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group, (1-hydroxyimino) butyl group and the like. Of these, (1-hydroxyimino) C1-6 alkyl groups are preferred.
In the “optionally substituted (1-hydroxyimino) C1-12 alkyl group”, the hydrogen atom on the hydroxyl group is substituted with the “optionally substituted C1-12 alkyl group”. Examples of the “group” include methoxyiminomethyl group, (1-ethoxyimino) methyl group, (1-ethoxyimino) ethyl group, and the like. Of these, (1- (C1-6 alkoxy) imino) C1-6 alkyl groups are preferred.
　Ｘ及びＸ’の「置換基を有してもよいアミノ基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「アミノ基」としては、例えば、メチルアミノ基、エチルアミノ基、ジメチルアミノ基、ジエチルアミノ基等が挙げられる。これらのうち、モノＣ１～６アルキルアミノ基又はジＣ１～６アルキルアミノ基が好ましい。
　また、アミノ基上の２つの水素原子が、「置換基を有してもよいＣ１～１２アルキル基」の同一の炭素原子で置換された「基」としては、例えば、メチリデンアミノ基、エチリデンアミノ基等が挙げられる。これらのうち、モノＣ１～６アルキリデンアミノ基が好ましい。
　また、上記以外にも、例えば、フェニルアミノ基、４－メチルフェニルアミノ基等のモノアリールアミノ基（好ましくはモノＣ６～１２アリールアミノ基）；ジ１－ナフチルアミノ基等のジアリールアミノ基（好ましくはジＣ６～１２アリールアミノ基）；アセチルアミノ基、ベンゾイルアミノ基等のアシルアミノ基（好ましくはＣ１～６アシルアミノ基）等が挙げられる。 Examples of the “amino group” substituted by the “optionally substituted C1-12 alkyl group” in the “optionally substituted amino group” of X and X ′ include, for example, a methylamino group , Ethylamino group, dimethylamino group, diethylamino group and the like. Of these, a mono C1-6 alkylamino group or a di C1-6 alkylamino group is preferable.
Examples of the “group” in which two hydrogen atoms on the amino group are substituted with the same carbon atom of the “optionally substituted C1-12 alkyl group” include, for example, a methylideneamino group and an ethylideneamino group Etc. Of these, mono C1-6 alkylideneamino groups are preferred.
In addition to the above, for example, monoarylamino groups such as phenylamino group and 4-methylphenylamino group (preferably monoC6-12 arylamino group); diarylamino groups such as di1-naphthylamino group (preferably Are diC6-12 arylamino groups); acylamino groups such as acetylamino group and benzoylamino group (preferably C1-6 acylamino groups).
　Ｒ、Ｘ及びＸ’の「置換基を有してよいＣ１～１２アシル基」において、「置換基を有してよいＣ１アシル基」が「置換基を有するアミノ基」により置換された「基」としては、すなわち、「置換基を有するカルバモイル基」である。この「置換基を有するカルバモイル基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「カルバモイル基」としては、例えば、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等が挙げられる。これらのうち、モノＣ１～６アルキルカルバモイル基又はジＣ１～６アルキルカルバモイル基が好ましい。
　また、上記以外にも、例えば、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等のモノアリールカルバモイル基（好ましくはモノＣ６～１２アリールカルバモイル基）；アセチルカルバモイル基、ベンゾイルカルバモイル基等のアシルカルバモイル基（好ましくはＣ１～６アシルカルバモイル基）等が挙げられる。 In the “optionally substituted C1-12 acyl group” of R, X and X ′, “the substituted C1 acyl group” is replaced by “the substituted amino group” "Is a" carbamoyl group having a substituent ". In this “carbamoyl group having a substituent”, examples of the “carbamoyl group” substituted by the “optionally substituted C1-12 alkyl group” include, for example, a methylcarbamoyl group, an ethylcarbamoyl group, a dimethylcarbamoyl group And diethylcarbamoyl group. Of these, a mono C1-6 alkylcarbamoyl group or a diC1-6 alkylcarbamoyl group is preferable.
In addition to the above, for example, carbamoyl group; monoarylcarbamoyl group such as phenylcarbamoyl group and 4-methylphenylcarbamoyl group (preferably mono C6-12 arylcarbamoyl group); acyl such as acetylcarbamoyl group and benzoylcarbamoyl group And a rucarbamoyl group (preferably a C1-6 acylcarbamoyl group).
　Ｘ及びＸ’の「置換基を有しても良いメルカプト基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「メルカプト基」としては、例えば、メチルチオ基、エチルチオ基等が挙げられる。これらのうち、Ｃ１～６アルキルチオ基が好ましい。また、上記以外にも、例えば、フェニルチオ基、４－メチルフェニルチオ基等のアリールチオ基（好ましくはＣ６～１２アリールチオ基）、アセチルチオ基、ベンゾイルチオ基等のアシルチオ基（好ましくはＣ１～６アシルチオ基）等が挙げられる。 Examples of the “mercapto group” substituted by the “optionally substituted C1-12 alkyl group” in the “optionally substituted mercapto group” for X and X ′ include, for example, a methylthio group, An ethylthio group etc. are mentioned. Of these, C1-6 alkylthio groups are preferred. In addition to the above, for example, an arylthio group such as a phenylthio group and a 4-methylphenylthio group (preferably a C6-12 arylthio group), an acylthio group such as an acetylthio group and a benzoylthio group (preferably a C1-6 acylthio group) ) And the like.
　Ｒ、Ｘ及びＸ’の「置換基を有するスルホニル基」において、「置換基を有してもよいＣ１～１２アルキル基」により置換された「スルホニル基」としては、例えば、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、イソプロピルスルホニル基、ｎ－ブチルスルホニル基、イソ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、イソ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、イソヘキシルスルホニル基等が挙げられる。これらのうち、Ｃ１～６アルキルスルホニル基が好ましい。
　また、上記以外にも、例えば、トリフルオロメチルスルホニル基等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等のアリールスルホニル基（好ましくはＣ６～１２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等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等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又はジ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等のモノアリールスルファモイル基（好ましくはモノＣ６～１２アリールスルファモイル基）等が挙げられる。 Examples of the “sulfonyl group” substituted by the “optionally substituted C1-12 alkyl group” in the “sulfonyl group having a substituent” of R, X and X ′ include, for example, a methylsulfonyl group, ethyl Sulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, s-butylsulfonyl group, t-butylsulfonyl group, n-pentylsulfonyl group, isopentylsulfonyl group, neopentylsulfonyl group 1-ethylpropylsulfonyl group, n-hexylsulfonyl group, isohexylsulfonyl group and the like. Of these, C1-6 alkylsulfonyl groups are preferred.
In addition to the above, for example, 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 a C6- 12 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 Sulfamoyl groups such as N, N-dimethylsulfamoyl group, N, N-diethylsulfamoyl group (preferably mono-C1-6 alkylsulfamoyl group or di-C1-6 alkylsulfamoyl group); phenyl Sulfamoyl group, 4-methyl Naphthoylmethyl acylsulfamoyl monoaryl sulfamoyl group such as (preferably mono C6 ~ 12 aryl sulfamoyl group).
　Ｒ、Ｘ及びＸ’において、「置換基を有する」、「置換基を有してもよい」の「置換基としては」、上記以外にも、例えば、－Ｓｉ（Ｍｅ）３、－ＳｉＰｈ３、－Ｓｉ（ｃＰｒ）３、－Ｓｉ(Ｍｅ)２（ｔＢｕ）（ｔＢｕはターシャリーブチル基を表す。以下同じ。）等の－Ｓｉ（Ｒ１）（Ｒ２）（Ｒ３）で表される基等が挙げられる。 In R, X and X ′, “as the substituent” of “having a substituent” or “may have a substituent”, other than the above, for example, —Si (Me) 3 , —SiPh 3 , -Si (c Pr) 3, -Si (Me) 2 (t Bu) (t Bu represents a tertiary butyl group. hereinafter the same.), such as -Si (R 1) (R 2 ) (R 3) Group represented by these.
　式（Ｉ）において、Ａは夫々独立して、炭素原子、窒素原子、酸素原子又は硫黄原子を示し、ｎは１又は２の整数を示す。実線と点線の二重線は単結合又は２重結合を示す。すなわちＡを含む環は５員又は６員環であり、飽和環、部分不飽和環又は不飽和環を形成する。
　具体的には、式（Ｉ）中の In the formula (I), A independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and n represents an integer of 1 or 2. A solid line and a dotted double line indicate a single bond or a double bond. That is, the ring containing A is a 5-membered or 6-membered ring, and forms a saturated ring, a partially unsaturated ring, or an unsaturated ring.
Specifically, in the formula (I)
Figure JPOXMLDOC01-appb-C000004
Figure JPOXMLDOC01-appb-C000004
としては、 as,
Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005
等が挙げられる。 Etc.
　本発明化合物の塩としては、農園芸学的に許容される塩であれば、特に制限されない。例えば、塩酸、硫酸等の無機酸の塩；酢酸、乳酸等の有機酸の塩；リチウム、ナトリウム、カリウム等のアルカリ金属の塩；カルシウム、マグネシウム等のアルカリ土類金属の塩；鉄、銅等の遷移金属の塩；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、ヒドラジン等の有機塩基の塩等が挙げられる。 The salt of the compound of the present invention is not particularly limited as long as it is an agriculturally and horologically acceptable salt. For example, 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; iron and copper And salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like.
　式（Ｉ）～（ＩＩＩ）で表される化合物として具体的には例えば、表１～表３の化合物が例示できる。なお、表中、Ｍｅはメチル、Ｅｔはエチル、ｉＰｒはｉ－プロピル、ｎＰｒはｎ－プロピル、ｃＰｒはｃ－プロピル、ｔＢｕはｔ－ブチル、Ａｃはアセチル、Ｂｎはベンジル、Ｐｈはフェニル、Ｐｙはピリジルを表す。 Specific examples of the compounds represented by formulas (I) to (III) include the compounds in Tables 1 to 3. In the table, Me is methyl, Et is ethyl, i Pr is i-propyl, n Pr is n-propyl, c Pr is c-propyl, t Bu is t-butyl, Ac is acetyl, Bn is benzyl, Ph Represents phenyl and Py represents pyridyl.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-I000001
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-I000001
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-I000002
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-I000002
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-I000003
Figure JPOXMLDOC01-appb-I000004
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-I000003
Figure JPOXMLDOC01-appb-I000004
（製造法）
　本発明の化合物は、例えば、公知の方法により製造することができるが、たとえば、下記のようにして製造することができる。 (Production method)
Although the compound of this invention can be manufactured by a well-known method, for example, it can manufacture as follows, for example.
Figure JPOXMLDOC01-appb-C000006
 （式中、Ｘ、Ｘ’、ｍ及びｓは前記と同じ意味を表す。）
式（１）で表される化合物を、アルキルリチウム試薬を用いてリチオ化し、式（２）で表される化合物を添加して、式（３）で表される化合物を製造する。この場合、用いるアルキルリチウム試薬としては、メチルリチウム、ｎ－ブチルリチウム、ｓ－ブチルリチウム、ｔ－ブチルリチウム、リチウムジイソプロピルアミド（ＬＤＡ）等が挙げられる。溶媒としては、無水の反応系を構成でき、用いる化合物を溶解し、反応あるいは何らかの特段の相互作用をしなければ制限無く用いることが出来る。好適な例としては、ペンタン、ヘキサン、ヘプタン、アイソパー（登録商標）Ｅ、アイソパー（登録商標）Ｇ等のアルカン系、ベンゼン、トルエン、オルトキシレン等の芳香族系、ジエチルエーテル、ＴＨＦ等のエーテル系溶媒、およびこれらの溶媒を混合して用いることができ、ジエチルエーテル、ＴＨＦ等のエーテル系溶媒が好ましい。反応時は窒素雰囲気下等で無水系とし、－１０℃～－７８℃の温度において調製することができる。
Figure JPOXMLDOC01-appb-C000006
 (Wherein X, X ′, m and s represent the same meaning as described above.)
The compound represented by the formula (1) is lithiated using an alkyl lithium reagent, and the compound represented by the formula (2) is added to produce the compound represented by the formula (3). In this case, examples of the alkyllithium reagent used include methyllithium, n-butyllithium, s-butyllithium, t-butyllithium, lithium diisopropylamide (LDA), and the like. As the solvent, an anhydrous reaction system can be constructed, and the compound to be used can be used without limitation unless it dissolves the compound and does not react or have any special interaction. Preferred examples include alkanes such as pentane, hexane, heptane, Isopar (registered trademark) E, and Isopar (registered trademark) G, aromatics such as benzene, toluene, and orthoxylene, and ethers such as diethyl ether and THF. A solvent and a mixture of these solvents can be used, and ether solvents such as diethyl ether and THF are preferred. During the reaction, it can be made anhydrous in a nitrogen atmosphere or the like and can be prepared at a temperature of −10 ° C. to −78 ° C.
Figure JPOXMLDOC01-appb-C000007
 （式中、Ｘ、Ｘ’、ｍ及びｓは前記と同じ意味を表す。）
式（３）で表される化合物を、酸化反応により、式（４）で表される化合物を製造する。酸化反応は、２級水酸基を酸化できる反応であれば、特に限定することなく行うことができる。例えば、Jones酸化、オゾン酸化、Swern酸化等の酸化法、又は二酸化マンガン、デス・マーチン試薬等の酸化試薬を用いる方法が挙げられる。
Figure JPOXMLDOC01-appb-C000007
 (Wherein X, X ′, m and s represent the same meaning as described above.)
A compound represented by the formula (4) is produced by oxidizing the compound represented by the formula (3). The oxidation reaction can be performed without any particular limitation as long as it is a reaction capable of oxidizing the secondary hydroxyl group. Examples thereof include an oxidation method such as Jones oxidation, ozone oxidation, and Swern oxidation, or a method using an oxidation reagent such as manganese dioxide and Dess-Martin reagent.
Figure JPOXMLDOC01-appb-C000008
 （式中、Ｒ、Ｘ、Ｘ’、ｍ及びｓは前記と同じ意味を表す。）
式（４）で表される化合物と、式（５）で表される化合物を、脱水縮合し、オキシムを生成することで、本発明の式（ＩＩＩ）で表される化合物を製造する。オキシムの生成は、既知の方法において、式（５）の化合物もしくはその塩酸塩との反応によりエタノールのような溶媒中で、必要に応じて塩基、例えば、ピリジン、酢酸ナトリウム又は水性水酸化ナトリウム溶液を添加して、溶媒の沸点までの温度において調製することができる。
Figure JPOXMLDOC01-appb-C000008
 (Wherein R, X, X ′, m and s have the same meaning as described above.)
The compound represented by the formula (III) of the present invention is produced by dehydrating and condensing the compound represented by the formula (4) and the compound represented by the formula (5) to produce an oxime. The formation of the oxime is carried out in a known manner in a solvent such as ethanol by reaction with the compound of formula (5) or its hydrochloride, optionally in a base such as pyridine, sodium acetate or aqueous sodium hydroxide solution. Can be prepared at temperatures up to the boiling point of the solvent.
２）農園芸用殺菌剤
　本発明はまた、本発明の式（Ｉ）～（ＩＩＩ）で表される含窒素ヘテロ環化合物又はその塩の少なくとも１種を有効成分として含有する農園芸用殺菌剤（以下、「本発明殺菌剤」ということがある。）である。 2) Agricultural and horticultural fungicide The present invention also provides an agricultural and horticultural fungicide containing, as an active ingredient, at least one of the nitrogen-containing heterocyclic compounds represented by the formulas (I) to (III) of the present invention or salts thereof. (Hereafter, it may be called "the present invention bactericide").
　本発明殺菌剤は本発明化合物を有効成分として含有し、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 fungicide of the present invention contains the compound of the present invention as an active ingredient, and a wide variety of filamentous fungi such as algae (Omycetes), Ascomycetes, Deuteromycetes, basidiomycetes It has excellent bactericidal power against bacteria belonging to (Basidiomycetes).
　本発明殺菌剤は、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に、種子処理、茎葉散布、土壌施用又は水面施用等により使用することができる。 The fungicide of the present invention can be used by seed treatment, foliage spraying, soil application, water application, etc., for the control of various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf and grass.
　例えば、
テンサイ　　褐斑病（Ｃｅｒｃｏｓｐｏｒａ　ｂｅｔｉｃｏｌａ）
　　　　　　黒根病（Ａｐｈａｎｏｍｙｃｅｓ　ｃｏｃｈｌｌｏｉｄｅｓ）
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）
　　　　　　つる枯病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｍｅｌｏｎｉｓ）
　　　　　　菌核病（Ｓｃｌｅｒｏｔｉｎｉａ　ｓｃｌｅｒｏｔｉｏｒｕｍ）
　　　　　　灰色かび病（Ｂｏｔｒｙｔｉｓ　ｃｉｎｅｒｅａ）
　　　　　　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）
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）
イチゴ　　　灰色かび病（Ｂｏｔｒｙｔｉｓ　ｃｉｎｅｒｅａ）
　　　　　　うどんこ病（Ｓｏｈａｅｒｏｔｈｅｃａ　ｈｕｍｕｌｉ）
　　　　　　炭そ病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ａｃｕｔａｔｕｍ、Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｆｒａｇａｒｉａｅ）
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）
キャベツ　　根こぶ病（Ｐｌａｓｍｏｄｉｏｐｈｏｒａ　ｂｒａｓｓｉｃａｅ）
　　　　　　軟腐病（Ｅｒｗｉｎｉａ　ｃａｒｏｔｏｖｏｒａ）
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）
　　　　　　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（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｇｌｏｅｏｓｐｒｉｏｉｄｅｓ）
　　　　　　褐斑病（Ｄｉｐｌｏｃａｒｐｏｎ　ｍａｌｉ）
カキ　　　　うどんこ病（Ｐｈｙｌｌａｃｔｉｎｉａ　ｋａｋｉｃｏｌａ）
　　　　　　炭そ病（Ｇｌｏｅｏｓｐｏｒｉｕｍ　ｋａｋｉ）
　　　　　　角斑落葉病（Ｃｅｒｃｏｓｐｏｒａ　ｋａｋｉ） For example,
Sugar beet brown spot (Cercospora beticola)
Black root disease (Aphanomyces cochlloides)
Peanut brown spot (Mycosphaerella arachidis)
Black astringent disease (Mycosphaerella berkeleyi)
Cucumber powdery mildew (Sphaerotheca furiginea)
Vine Blight (Mycosphaella melonis)
Sclerotinia sclerotiorum
Gray mold disease (Botrytis cinerea)
Black star disease (Cladosporium cucumerinum)
Brown spot disease (Corynespora casiccola)
Seedling Blight (Phythium debaryanam, Rhizoctonia solani Kuhn)
Spotted bacterial disease (Pseudomonas syringae pv. Lecrymans)
Tomato gray mold (Botrytis cinerea)
Leaf mold (Cladosporium fulvum)
Eggplant gray mold (Botrytis cinerea)
Black blight (Corynespora melogenae)
Powdery mildew (Erysiphe cichoracerarum)
Susmolder disease (Mycovellosi natrassii)
Strawberry Gray mold disease (Botrytis cinerea)
Powdery mildew (Sohaerotheca humuli)
Anthracnose (Colletotrichum acutatum, Colletotrichum fragariae)
Onion gray rot (Botrytis allii)
Gray mold disease (Botrytis cinerea)
White spotted leaf blight (Botrytis squamosa)
Cabbage root-knot disease (Plasmodiophora brassicae)
Soft rot (Erwinia carotovora)
Kidney bean sclerotia (Sclerotinia sclerotiorum)
Gray mold disease (Botrytis cinerea)
Apple powdery mildew (Podosphaera leukotrica)
Venturia inaequalis
Moniria disease
Rot rot (Valsa mali)
Spotted leaf fall (Alternaria mary)
Red Star Disease (Gymnosporium yamadae)
Ring-shaped disease (Botryosphaeria berengeriana)
Anthracnose (Colletotrichum gloeosprioides)
Brown spot disease (Diplocarpon mary)
Oyster powdery mildew (Phyllactinia kakicola)
Anthracnose (Gloeosporium kaki)
Spotted leaf disease (Cercospora kaki)
モモ・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）
ナシ　　　　黒星病（Ｖｅｎｔｕｒｉａ　ｎａｓｈｉｃｏｌａ）
　　　　　　赤星病（Ｇｙｍｎｏｓｐｏｒａｎｇｉｕｍ　ａｓｉａｔｉｃｕｍ）
　　　　　　黒斑病（Ａｌｔｅｒｎａｒｉａ　ｋｉｋｕｃｈｉａｎａ）
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 out ash scab (Monilinia fracticola)
Grapes Gray mold (Botrytis cinerea)
Powdery mildew (Uncinula necator)
Late rot (Glomerella cingulata)
Pear black scab (Venturia nashicola)
Red Star Disease (Gymnosporium asiaticum)
Black spot disease (Alternaria kikuchiana)
Cha ring spot disease (Pestaloti theae)
Colletotrichum theae-sinensis citrus scab (Elsinoe fawceti)
Blue mold disease (Penicillium italicum)
Green mold (Penicillium digitatum)
Gray mold disease (Botrytis cinerea)
Black spot disease (Diaporthe citri)
Sickness disease (Xanthomonas campestris pv. Citri)
Wheat powdery mildew (Erysiphe graminis f. Sp. Tritici)
Red mold disease (Gibberella zeae)
Red rust (Puccinia recondita)
Brown snow rot (Pythium iwayamai)
Scarlet Snow Rot (Monographella nivalis)
Eye disease (Pseudocercosporella herpotriochoides)
Leaf blight (Septoria tritici)
Blight disease (Leptosphaeria nodorum)
Typhula incarnata (Typhula incarnata)
Snow rot large mycobacterial disease (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　ｎｉｙａｂｅａｎｕｓ）
　　　　　　苗立枯病（Ｐｙｔｈｉｕｍ　ｇｒａｍｉｎｉｃｏｌｕｍ）
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）
キュウリ　　べと病（Ｐｓｅｕｄｏｐｅｒｏｎｏｓｐｏｒａ　ｃｕｂｅｎｓｉｓ）
ブドウ　　　べと病（Ｐｌａｓｍｏｐａｒａ　ｖｉｔｉｃｏｌａ）
等の防除に使用することができる。 Barley leaf spot (Pyrenophora graminea)
Rhynchosporium secalis
Bare Scab (Ustilago tritici, U. nuda)
Rice blast disease (Pyricularia oryzae)
Rhizoctonia solani
Idiot Seedling (Gibberella fujikuroi)
Sesame leaf blight (Cochliobolus niyabeanus)
Seedling blight (Pythium gramicolium)
Tobacco sclerotia (Sclerotinia sclerotiorum)
Powdery mildew (Erysiphe cichoracerarum)
Botrytis cinerea
Bentgrass Snow rot large sclerotia nuclear disease (Sclerotinia borealis)
Red fire disease (Pythium aphanidermatum)
Orchardgrass powdery mildew (Erysiphe graminis)
Soybean Purpura (Cercospora kikuchii)
Downy mildew (Peronospora Manshurica)
Phytophthora sojae
Potato and tomato plague (Phytophthora infestans)
Cucumber downy mildew (Pseudoperonospora cubensis)
Grape downy mildew (Plasmopara viticola)
It can be used for the control of etc.
　また、近年種々の病原菌においてベンズイミダゾール系殺菌剤やジカルボキシイミド系殺菌剤等に対する耐性が発達し、それらの薬剤の効力不足を生じており、耐性菌にも有効な薬剤が望まれている。本発明殺菌剤は、それら薬剤に対し感受性の病原菌のみならず、耐性菌にも優れた殺菌効果を有する。 In recent years, resistance to benzimidazole fungicides and dicarboximide fungicides has been developed in various pathogenic bacteria, resulting in insufficient efficacy of these drugs, and drugs effective against resistant bacteria are desired. The bactericidal agent of the present invention has an excellent bactericidal effect not only on pathogenic bacteria sensitive to these drugs but also on resistant bacteria.
　例えば、チオファネートメチル、ベノミル、カルベンダジム等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）に対しても感受性菌と同様に、本発明殺菌剤は有効である。 For example, gray mold fungus (Botrytis cinerea), sugar beet brown fungus (Cercospora beticola), Venturia inaequalis, Venturia inaquali (Venturia inaequalis), Nent black urinaria (Venturia inaequilis) The fungicides of the present invention are also effective against).
　さらに、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）に対しても感受性菌と同様に、本発明殺菌剤は有効である。 Furthermore, the fungicides of the present invention are also effective against gray mold fungi (Botrytis cinerea) that are resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione).
　適用がより好ましい病害としては、テンサイの褐斑病、コムギのうどんこ病、イネのいもち病、リンゴ黒星病、キュウリの灰色かび病、ラッカセイの褐斑病等が挙げられる。 Favorable diseases that can be applied include brown spot of sugar beet, powdery mildew of wheat, rice blast, rice black spot, gray mold of cucumber, and brown spot of peanut.
　また、本発明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。
　本発明殺菌剤を実際に施用する際には、本発明化合物を他成分を加えることなく純粋な形で使用するものであっても、農薬として使用する目的で一般の農薬のとり得る形態、即ち、水和剤、粒剤、粉剤、乳剤、水溶剤、懸濁剤、顆粒水和剤等の農薬製剤の形態で使用するものであってもよい。 The fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
When the fungicide of the present invention is actually applied, even if the compound of the present invention is used in a pure form without adding other components, a form that can be taken by a general pesticide for the purpose of use as an agrochemical, , Wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, granular wettable powders and the like.
　農薬製剤中に添加することのできる添加剤及び担体としては、固体の剤型を目的とする場合は、大豆粉、小麦粉等の植物性粉末、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、クレー等の鉱物性微粉末、安息香酸ソーダ、尿素、芒硝等の有機及び無機化合物が使用される。 Additives and carriers that can be added to the agrochemical formulation include vegetable powders such as soybean flour and wheat flour, diatomaceous earth, apatite, gypsum, talc, bentonite, and pyrophyllite for solid dosage forms. Organic and inorganic compounds such as mineral fine powders such as clay, sodium benzoate, urea, and sodium sulfate are used.
　また、液体の剤型を目的とする場合は、ケロシン、キシレン及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、水等を溶剤として使用することができる。 For liquid dosage forms, kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, Water or the like can be used as a solvent.
　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、必要に応じ界面活性剤を添加することもできる。
　添加することができる界面活性剤としては特に限定はないが、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等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等が挙げられる。 Furthermore, in order to take a uniform and stable form in these preparations, a surfactant may be added as necessary.
The surfactant that can be added is not particularly limited. For example, alkylphenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, polyoxyethylene Sorbitan higher fatty acid ester added with polyoxyethylene, nonionic surfactant such as tristyryl phenyl ether added with polyoxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfuric acid of higher alcohol Examples thereof include ester salts, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and isobutylene-maleic anhydride copolymers.
　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、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散布し、粉剤・粒剤はそのまま植物に散布する方法で使用される。 The wettable powder, emulsion, flowable powder, aqueous solvent, and granular wettable powder thus obtained are diluted with water to a predetermined concentration and sprayed as a solution, suspension, or emulsion. Granules are used as they are sprayed on plants.
　本発明殺菌剤中における有効成分量は、通常、組成物（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 fungicide of the present invention is usually preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the entire composition (formulation).
　本発明殺菌剤の施用量は、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、対象作物等により異なるが、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 fungicide of the present invention varies depending on weather conditions, formulation form, application time, application method, application location, disease to be controlled, target crop, etc., but usually 1 to 1,000 g in terms of the amount of the active ingredient compound per hectare. It is preferably 10 to 100 g.
　水和剤、乳剤、懸濁剤、水溶剤、顆粒水和剤等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, etc. are diluted with water and applied, the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
　本発明殺菌剤には、本発明化合物のほかに、各種の殺菌剤や殺虫・殺ダニ剤、共力剤の１種又は２種以上を混合することもできる。 In addition to the compounds of the present invention, one or two or more of various fungicides, insecticides / miticides, and synergists can be mixed with the fungicide of the present invention.
　本発明化合物と混合して使用できる殺菌剤、殺虫剤、殺ダニ剤、植物生長調節剤の代表例を以下に示す。 Representative examples of fungicides, insecticides, acaricides, and plant growth regulators that can be used in combination with the compounds of the present invention are shown below.
殺菌剤：
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 メチル等のベンゾイミダゾール系；
クロゾリネート、イプロジオン、プロシミドン、ビンクロゾリン等のジカルボキシイミド系；
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、イプコナゾール、イミベンコナゾール、等のＤＭＩ－殺菌剤；
ベナラキシル、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、オフラセ等のフェニルアミド系；
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、スピロキサミン等のアミン系；
ＥＤＤＰ、イプロベンホス、ピラゾホス等のホスホロチオレート系；
イソプロチオラン等のジチオラン系；
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、チフルザミド等のカルボキサミド；ブピリメート、ジメチリモル、エチリモル等のヒドロキシ－（２－アミノ）ピリミジン；シプロジニル、メパニピリム、ピリメタニル等のＡＰ殺菌剤 (アニリノピリミジン) ；
ジエトフェンカルブ等のＮ－フェニルカーバメート；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、メトミノフェン等のQＱｏＩ－殺菌剤 (Ｑｏ阻害剤)；
フェンピコニル、フルジオキソニル等のＰＰ殺菌剤 (フェニルピロール) ；
キノキシフェン等のキノリン系 ；
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－メチル等のＡＨ殺菌剤 (芳香族炭化水素）；
フサライド、ピロキロン、トリシクラゾール等のＭＢＩ－Ｒ；
カルプロパミド、ジクロシメット、フェノキサニル等のＭＢＩ－Ｄ；
フェンヘキサミド、ピリブチカルブ、タービナフィン等のＳＢＩ剤；
ペンシクロン等のフェニルウレア；
シアゾファミド等のＱｉＩ－殺菌剤（Ｑｉ阻害剤）；
ゾキサミド等のベンズアミド；
ブラストサイジン、ミルディオマイシン等のエノピランウロン；
カスガマイシン等のへキソピラノシル；
ストレプトマイシン、バリダマイシン等のグルコピラノシル；
シモキサニル等のシアノアセトアミド；
プロパモカルブ、プロチオカルブ、ポリカーバメート等のカーバメート；
ビナパクリル、ジノカップ、フェリムゾン、フルアジナム等の脱共役剤；
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等の有機スズ化合物；
亜リン酸、トルクロホスメチル、ホセチル等のリン酸エステル；
テクロフタラム等のフタルアミド酸；
トリアゾキシド等のベンゾトリアジン；
フルスルファミド等のベンゼンスルフォナミド；
ジクロメジン等のピリダジノン；
ジメトモルフ、フルモルフ、ベンチアバリカルブ、イプロバリカルブ、マンジプロパミド等のＣＡＡ殺菌剤 (カルボン酸アミド)；
オキシテトラサイクリン等のテトラサイクリン；
メタスルホカルブ等のチオカーバメート；
エトリジアゾール、ポリオキシン、オキソリニック酸、ヒドロキシイソキサゾール、オクチノリン、シルチオファム、ジフルメトリム、アシベンゾラルＳメチル、プロベナゾール、チアジニル、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、水酸化第二銅、有機銅、硫黄、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、メタムナトリウム塩、キノメチオネート、シプロフラム、シルチオファム、アグロバクテリウム、フルオルイミド等のその他の化合物。 Fungicide:
Benzimidazoles such as benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl;
Dicarboximides such as clozolinate, iprodione, procymidone, vinclozolin;
Imazaril, oxpoconazole, pefazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, full Quinconazole, flusilazole, flutriazole, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, prothioconazole, cimeconazole, tebuconazole, tetraconazole, triadimethone, triazimenol, triticonazole, ethaconazole DMI-bactericides such as urconazole cis, ipconazole, imibenconazole, etc.
Phenylamides such as benalaxyl, furaxyl, metalaxyl, metalaxyl-M, oxadixyl, and ophthalase;
Amines such as aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
Phosphorothiolate systems such as EDDP, iprobenphos, pyrazophos;
Dithiolanes such as isoprothiolane;
Carboxamides such as benodanyl, boscalid, carboxin, fenfuran, flutolanil, furametopyr, mepronyl, oxycarboxyl, penthiopyrad, tifluzamide; hydroxy- (2-amino) pyrimidines such as buprimate, dimethylylmol, ethylimyl; AP fungicide (anilinopyrimidine);
N-phenylcarbamate such as dietofencarb; azoxystrobin, picoxystrobin, pyraclostrobin, cresoxime-methyl, trifloxystrobin, dimoxystrobin, metminostrobin, orizastrobin, famoxadone, floxastrobin QQoI-bactericides (Qo inhibitors) such as phenamidon, metminophen;
PP fungicides (phenylpyrrole) such as fenpiconyl, fludioxonil;
Quinoline series such as quinoxyphene;
AH fungicides (aromatic hydrocarbons) such as biphenyl, chloronebu, dichlorane, kintozen, technazen, tortofos-methyl;
MBI-R such as fusalide, pyrokilone, tricyclazole;
MBI-D such as carpropamide, diclocimet, phenoxanyl;
SBI agents such as fenhexamide, pyributycarb, terbinafine;
Phenyl urea such as pencyclon;
QiI-bactericides (Qi inhibitors) such as cyazofamid;
Benzamides such as zoxamide;
Enopyran urones such as blasticidin, mildiomycin;
Hexopyranosyl such as kasugamycin;
Glucopyranosyl such as streptomycin, validamycin;
Cyanoacetamide such as simoxanyl;
Carbamates such as propamocarb, prothiocarb, and polycarbamate;
Uncoupling agents such as vinapacryl, zinocup, ferrimzone, fluazinam;
Organotin compounds such as triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide;
Phosphoric acid esters such as phosphorous acid, tolcrofosmethyl, fosetyl
Phthalamic acid such as teclophthalam;
Benzotriazines such as triazoxide;
Benzenesulfonamide such as fursulfamide;
Pyridazinones such as dichromedin;
CAA fungicides (carboxylic amides) such as dimethomorph, flumorph, bench avaricarb, iprovaricarb, mandipropamide;
Tetracyclines such as oxytetracycline;
Thiocarbamates such as metasulfocarb;
Etridiazole, polyoxin, oxolinic acid, hydroxyisoxazole, octinoline, sylthiophane, diflumetrim, acibenzoral S methyl, probenazole, thiazinyl, ethaboxam, cyflufenamide, proquinazide, metolaphenone, fluopicolide, cupric hydroxide, organic copper, sulfur, farbum, manzeb , Mannebu, metyram, propineb, thiuram, dineb, ziram, captan, captahol, phorpet, chlorothalonil, diclofluuride, tolylfluanid, dodine, guazatine, iminotadine acetate, iminotadine dodecylbenzenesulfonate, anilazine, dithianone, chloro Picrine, Dazomet, Metam sodium salt, Quinomethionate, Ciprofram, Silthiofam, Agrova Agrobacterium, other compounds, such as Furuoruimido.
殺虫・殺ダニ剤：
有機燐及びカーバメート系殺虫剤：
　フェンチオン、フェニトロチオン、ダイアジノン、クロルピリホス、ＥＳＰ、バミドチオン、フェントエート、ジメトエート、ホルモチオン、マラソン、トリクロルホン、チオメトン、ホスメット、ジクロルボス、アセフェート、ＥＰＢＰ、メチルパラチオン、オキシジメトンメチル、エチオン、サリチオン、シアノホス、イソキサチオン、ピリダフェンチオン、ホサロン、メチダチオン、スルプロホス、クロルフェンビンホス、テトラクロルビンホス、ジメチルビンホス、プロパホス、イソフェンホス、エチルチオメトン、プロフェノホス、ピラクロホス、モノクロトホス、アジンホスメチル、アルディカルブ、メソミル、チオジカルブ、カルボフラン、カルボスルファン、ベンフラカルブ、フラチオカルブ、プロポキスル、ＢＰＭＣ、ＭＴＭＣ、ＭＩＰＣ、カルバリル、ピリミカーブ、エチオフェンカルブ、フェノキシカルブ、ＥＤＤＰ等。
ピレスロイド系殺虫剤：
　ペルメトリン、シペルメトリン、デルタメスリン、フェンバレレート、フェンプロパトリン、ピレトリン、アレスリン、テトラメスリン、レスメトリン、ジメスリン、プロパスリン、フェノトリン、プロトリン、フルバリネート、シフルトリン、シハロトリン、フルシトリネート、エトフェンプロクス、シクロプロトリン、トロラメトリン、シラフルオフェン、ブロフェンプロクス、アクリナスリン等。
ベンゾイルウレア系その他の殺虫剤：
　ジフルベンズロン、クロルフルアズロン、ヘキサフルムロン、トリフルムロン、テトラベンズロン、フルフェノクスロン、フルシクロクスロン、ブプロフェジン、ピリプロキシフェン、メトプレン、ベンゾエピン、ジアフェンチウロン、アセタミプリド、イミダクロプリド、ニテンピラム、フィプロニル、カルタップ、チオシクラム、ベンスルタップ、硫酸ニコチン、ロテノン、メタアルデヒド、機械油、ＢＴや昆虫病原ウイルス等の微生物農薬等。 Insecticides and acaricides:
Organophosphorus and carbamate insecticides:
Fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formothione, marathon, trichlorfone, thiometone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimethone methyl, ethion, salicione, cyanophos, isoxathione, cyanophos, isoxathione Methidathione, Sulprophos, Chlorfenvinphos, Tetrachlorbinphos, Dimethylvinphos, Propafos, Isophenphos, Ethylthiomethone, Profenofos, Piracrofos, Monocrotophos, Adinfosmethyl, Aldicarb, Mesomil, Thiodicarb, Carbofuran, Carbosulfan, Benhracarb, Furatiocarb Propoxur, BPMC, M MC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, EDDP, and the like.
Pyrethroid insecticides:
Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, thoramethrin , Silafluophene, brofenprox, aclinasrin, etc.
Benzoylurea and other insecticides:
Diflubenzuron, Chlorfluazuron, Hexaflumuron, Triflumuron, Tetrabenzuron, Flufenoxuron, Flucycloxuron, Buprofezin, Pyriproxyfen, Metoprene, Benzoepine, Diafenthiuron, Acetamiprid, Imidacloprid, Nitenpyram, Fipronil, Cartap Thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.
殺線虫剤：
　フェナミホス、ホスチアゼート等。
殺ダニ剤：
　クロルベンジレート、フェニソブロモレート、ジコホル、アミトラズ、ＢＰＰＳ、ベンゾメート、ヘキシチアゾクス、酸化フェンブタスズ、ポリナクチン、キノメチオネート、ＣＰＣＢＳ、テトラジホン、アベルメクチン、ミルベメクチン、クロフェンテジン、シヘキサチン、ピリダベン、フェンピロキシメート、テブフェンピラド、ピリミジフェン、フェノチオカルブ、ジエノクロル等。
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。 Nematicides:
Phenamifos, phostiazates, etc.
Acaricide:
Chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexithiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor etc.
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 hydrazide maleate, 1- Naphtylacetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozeate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride.
　以下実施例によっ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。なお、実施例の化合物番号は、前記化合物の例示の表中の化合物番号に対応している。 Hereinafter, the present invention will be described in more detail by way of examples. However, the present invention is not limited to the following examples. In addition, the compound number of an Example respond | corresponds to the compound number in the table | surface of the illustration of the said compound.
（化合物の合成）
[実施例１]
(2-Bromophenyl)-3-quinolinyl-methanone O-methyloximeの製造（化合物番号Ａ３－６）（工程１）
　３－ブロモキノリン４．３８ｇ（２１．０ｍｍｏｌ）を６０ｍＬの脱水したジエチルエーテルに溶解し、－７８℃に冷却後ｔ-BuLi（１．７Ｍ　ｎ－ペンタン溶液）１３ｍＬを加えた。反応液を－７８℃で１．５時間撹拌した後、２－ブロモベンズアルデヒド４．０９ｇ（２２．１ｍｍｏｌ）を３０ｍＬの脱水ジエチルエーテルに溶解した溶液を－７８℃下で加え、さらに２時間、同温度で撹拌した。この反応混合液に－７８℃下で飽和塩化アンモニウム水１５０ｍＬを加えた後、水３００ｍＬと酢酸エチル３００ｍＬを加え分液した。有機層を水洗後硫酸マグネシウムで乾燥を行い、減圧下溶媒を留去し、得られた粗結晶をジエチルエーテルで洗浄し、α－（２－ブロモフェニル）－３－キノリンメタノール３．３ｇを得た。
（工程２）
　α－（２－ブロモフェニル）－３－キノリンメタノール４．２６ｇ（１３．５６ｍｍｏｌ）を１，４－ジオキサン６０ｍＬに溶解し、二酸化マンガン（８８％）８．３１ｇを加え、室温で一晩撹拌した。不溶物をセライト濾過で除去し、濾液を減圧下濃縮した。得られた粗結晶をｎ－ヘキサンとジエチルエーテルの混合液で洗浄することにより、（２－ブロモフェニル）－３－キノリニルメタノン３．９６ｇを得た。
（工程３）
　（２－ブロモフェニル）－３－キノリニルメタノン３．９６ｇ（１２．６９ｍｍｏｌ）を５０ｍＬのメタノールに溶解し、メトキシアミン塩酸塩１．２ｇ（１４．３６ｍｍｏｌ）を加えて２２時間加熱還流を行った。反応液にさらに０．２２ｇのメトキシアミン塩酸塩を加え、３時間加熱還流を行った後、減圧下濃縮し炭酸水素ナトリウム飽和溶液５０ｍＬを加え、酢酸エチルで抽出した。有機層を水洗後、硫酸マグネシウムで乾燥し、濃縮後残渣をシリカゲルカラムクロマトグラフィー（展開溶媒；ｎ－ヘキサン：酢酸エチル＝９：１）で精製し目的物３．７９ｇを得た。
　得られた目的物は、Ｅ体とＺ体比が１：２．４の混合物であった。
物性：amorphous
1H NMR (300 MHz, CDCl3)　δ 4.06 (s, 3H(2.4/3.4)), 4.09 (s, 3H(1/3.4)), 7.2-8.2 (m, 9H), 9.14(d, 1H(1/3.4), J= 2.4 Hz), 9.34 (d, 1H(2.4/3.4), J = 2.4 Hz) (Synthesis of compounds)
[Example 1]
Production of (2-Bromophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-6) (Step 1)
3.38 g (21.0 mmol) of 3-bromoquinoline was dissolved in 60 mL of dehydrated diethyl ether, cooled to −78 ° C., and 13 mL of t-BuLi (1.7 M n-pentane solution) was added. After stirring the reaction solution at −78 ° C. for 1.5 hours, a solution of 4.09 g (22.1 mmol) of 2-bromobenzaldehyde dissolved in 30 mL of dehydrated diethyl ether was added at −78 ° C., and the reaction solution was further added for 2 hours. Stir at temperature. To this reaction mixture, 150 mL of saturated aqueous ammonium chloride was added at −78 ° C., and then 300 mL of water and 300 mL of ethyl acetate were added to separate the layers. The organic layer was washed with water and dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting crude crystals were washed with diethyl ether to obtain 3.3 g of α- (2-bromophenyl) -3-quinolinemethanol. It was.
(Process 2)
4.26 g (13.56 mmol) of α- (2-bromophenyl) -3-quinolinemethanol was dissolved in 60 mL of 1,4-dioxane, 8.31 g of manganese dioxide (88%) was added, and the mixture was stirred overnight at room temperature. . Insoluble matter was removed by Celite filtration, and the filtrate was concentrated under reduced pressure. The obtained crude crystals were washed with a mixed solution of n-hexane and diethyl ether to obtain 3.96 g of (2-bromophenyl) -3-quinolinylmethanone.
(Process 3)
Dissolve 3.96 g (12.69 mmol) of (2-bromophenyl) -3-quinolinylmethanone in 50 mL of methanol, add 1.2 g (14.36 mmol) of methoxyamine hydrochloride, and heat to reflux for 22 hours. went. 0.22 g of methoxyamine hydrochloride was further added to the reaction solution, and the mixture was heated under reflux for 3 hours, then concentrated under reduced pressure, added with 50 mL of a saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. After concentration, the residue was purified by silica gel column chromatography (developing solvent; n-hexane: ethyl acetate = 9: 1) to obtain 3.79 g of the desired product.
The obtained target product was a mixture having an E-form ratio and a Z-form ratio of 1: 2.4.
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ 4.06 (s, 3H (2.4 / 3.4)), 4.09 (s, 3H (1 / 3.4)), 7.2-8.2 (m, 9H), 9.14 (d, 1H ( 1 / 3.4), J = 2.4 Hz), 9.34 (d, 1H (2.4 / 3.4), J = 2.4 Hz)
　同様にして以下の化合物を製造した。
［実施例２］
(2-Chlorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号Ａ３－２）
１：２．１ mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ4.07 (s, 3H(2.1/3.1)), 4.09 (s, 3H(1/3.1)), 7.2-7.9 (m, 9H), 9.12(d, 1H(1/3.1), J= 2.1 Hz), 9.35 (d, 1H(2.1/3.1), J = 2.1 Hz) In the same manner, the following compounds were produced.
[Example 2]
(2-Chlorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-2)
1: 2.1 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ4.07 (s, 3H (2.1 / 3.1)), 4.09 (s, 3H (1 / 3.1)), 7.2-7.9 (m, 9H), 9.12 (d, 1H (1 / 3.1), J = 2.1 Hz), 9.35 (d, 1H (2.1 / 3.1), J = 2.1 Hz)
［実施例３］
(3-Chlorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号Ａ３－３）
物性：amorphous
1H NMR (300 MHz, CDCl3) δ4.06 (s, 3H), 7.2-7.8 (m, 7H), 7.95 (d, 1H, J = 2.1 Hz), 8.12 (d, 1H, J = 8.6 Hz), 9.25 (d, 1H, J = 2.1 Hz) [Example 3]
(3-Chlorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-3)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ4.06 (s, 3H), 7.2-7.8 (m, 7H), 7.95 (d, 1H, J = 2.1 Hz), 8.12 (d, 1H, J = 8.6 Hz ), 9.25 (d, 1H, J = 2.1 Hz)
［実施例４］
(4-Chlorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号Ａ３－４）
1:2.5 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ4.01 (s, 3H(2.5/3.5)), 4.06 (s, 3H(1/3.5)), 7.2-8.2 (m, 9H), 8.90(d, 1H(2.5/3.5), J= 2.1 Hz), 9.24 (d, 1H(1/3.5), J = 2.1 Hz) [Example 4]
(4-Chlorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-4)
1: 2.5 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ4.01 (s, 3H (2.5 / 3.5)), 4.06 (s, 3H (1 / 3.5)), 7.2-8.2 (m, 9H), 8.90 (d, 1H (2.5 / 3.5), J = 2.1 Hz), 9.24 (d, 1H (1 / 3.5), J = 2.1 Hz)
［実施例５］
phenyl-3-quinolinyl-methanone O-methyloxime（化合物番号Ａ３－１）
1:1.3 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ4.02 (s, 3H(1.3/2.3)), 4.05 (s, 3H(1/2.3)), 7.33-7.60 (m, 6H), 7.68-7.83 (m, 2H), 7.96 (d, 1H(1/2.3), J = 2.1 Hz), 8.10-8.16 (m, 1H+1H(1.3/2.3)), 8.93 (d, 1H(1.3/2.3), J = 2.1 Hz), 9.26 (d, 1H(1/2.3), J = 2.1 Hz); MS (APCI, m/z) 263 ([M+1]+). [Example 5]
phenyl-3-quinolinyl-methanone O-methyloxime (Compound No. A3-1)
1: 1.3 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ4.02 (s, 3H (1.3 / 2.3)), 4.05 (s, 3H (1 / 2.3)), 7.33-7.60 (m, 6H), 7.68-7.83 (m , 2H), 7.96 (d, 1H (1 / 2.3), J = 2.1 Hz), 8.10-8.16 (m, 1H + 1H (1.3 / 2.3)), 8.93 (d, 1H (1.3 / 2.3), J = 2.1 Hz), 9.26 (d, 1H (1 / 2.3), J = 2.1 Hz); MS (APCI, m / z) 263 ([M + 1] + ).
［実施例６］
(3-fluorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号Ａ３－７）
1:1.5 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ4.02 (s, 3H(1.5/2.5)), 4.06 (s, 3H(1/2.5)), 7.0-8.2 (m, 9H), 8.91 (d, 1H(1.5/2.5), J= 1.8 Hz), 9.24 (d, 1H(1/2.5), J = 2.1 Hz); MS (APCI, m/z) 281 ([M+1]+). [Example 6]
(3-fluorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-7)
1: 1.5 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ4.02 (s, 3H (1.5 / 2.5)), 4.06 (s, 3H (1 / 2.5)), 7.0-8.2 (m, 9H), 8.91 (d, 1H (1.5 / 2.5), J = 1.8 Hz), 9.24 (d, 1H (1 / 2.5), J = 2.1 Hz); MS (APCI, m / z) 281 ([M + 1] + ).
［実施例７］
(3-fluorophenyl)-3-quinolinyl-methanone O-ethyloxime（化合物番号Ａ３－８）
1:1.3 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ1.29-1.38 (m, 3H), 4.26-4.36 (m, 2H), 7.0-8.2 (m, 9H), 8.95 (d, 1H(1.3/2.3), J = 2.4 Hz), 9.25 ( d, 1H(1/2.3), J = 2.1 Hz); MS (APCI,m/z) 295 ([M+1]+). [Example 7]
(3-fluorophenyl) -3-quinolinyl-methanone O-ethyloxime (Compound No. A3-8)
1: 1.3 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ1.29-1.38 (m, 3H), 4.26-4.36 (m, 2H), 7.0-8.2 (m, 9H), 8.95 (d, 1H (1.3 / 2.3), J = 2.4 Hz), 9.25 (d, 1H (1 / 2.3), J = 2.1 Hz); MS (APCI, m / z) 295 ([M + 1] + ).
［実施例８］ 
(3-fluorophenyl)-3-quinolinyl-methanone O-t-butyloxime（化合物番号Ａ３－９）
1:1.3 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ1.36 (s, 9H(1.3/2.3), 1.39 (s, 9H(1/2.3)), 7.0-8.2 (m, 9H), 8.99 (d, 1H(1.3/2.3), J = 2.4 Hz), 9.25 (d, 1H(1/2.3), J = 2.4 Hz); MS (APCI, m/z) 323 ([M+1]+). [Example 8]
(3-fluorophenyl) -3-quinolinyl-methanone Ot-butyloxime (Compound No. A3-9)
1: 1.3 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ1.36 (s, 9H (1.3 / 2.3), 1.39 (s, 9H (1 / 2.3)), 7.0-8.2 (m, 9H), 8.99 (d, 1H ( 1.3 / 2.3), J = 2.4 Hz), 9.25 (d, 1H (1 / 2.3), J = 2.4 Hz); MS (APCI, m / z) 323 ([M + 1] + ).
［実施例９］
(3-fluorophenyl)-3-quinolinyl-methanone O-benzyloxime（化合物番号Ａ３－１０）
1:1.7 mixtures (E, Z)
物性：nD 20.7=1.6415
1H NMR (300 MHz, CDCl3) δ5.26 (s, 2H(1.7/2.7)), 5.29 (s, 2H(1/2.7)), 7.0-8.2 (m, 9H), 8.92 (d, 1H(1.7/2.7), J= 2.1 Hz), 9.24 (m, d, 1H(1/2.7), J = 2.1 Hz); MS(APCI, m/z) 357 ([M+1]+). [Example 9]
(3-fluorophenyl) -3-quinolinyl-methanone O-benzyloxime (Compound No. A3-10)
1: 1.7 mixtures (E, Z)
Physical property: n D 20.7 = 1.6415
1 H NMR (300 MHz, CDCl 3 ) δ5.26 (s, 2H (1.7 / 2.7)), 5.29 (s, 2H (1 / 2.7)), 7.0-8.2 (m, 9H), 8.92 (d, 1H (1.7 / 2.7), J = 2.1 Hz), 9.24 (m, d, 1H (1 / 2.7), J = 2.1 Hz); MS (APCI, m / z) 357 ([M + 1] + ).
［実施例１０］
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号Ａ３－５）
1:2.5 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ4.06 (s, 3H(2.5/3.5)), 4.09 (s, 3H(1/3.5)), 7.2-8.2 (m, 8H), 9.11(d, 1H(1/3.5), J= 2.1 Hz), 9.34 (d, 1H(2.5/3.5), J = 2.1 Hz) [Example 10]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-5)
1: 2.5 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ4.06 (s, 3H (2.5 / 3.5)), 4.09 (s, 3H (1 / 3.5)), 7.2-8.2 (m, 8H), 9.11 (d, 1H (1 / 3.5), J = 2.1 Hz), 9.34 (d, 1H (2.5 / 3.5), J = 2.1 Hz)
［実施例１１］
(2-Isopropylphenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号Ａ３－１２）1:4.6 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ1.06 (d, 6H(1/5.6), J = 6.9 Hz), 1.24 (d, 6H(4.6/5.6),J = 6.9 Hz), 2.78 (hep, 1H(4.6/5.6), J = 6.9 Hz), 3.05 (hep, 1H(1/5.6), J = 6.9Hz), 4.02 (s, 3H(4.6/5.6)), 4.07(s, 3H(1/5.6)), 7.2-8.2 (m, 9H), 9.16(d, 1H(1/5.6), J = 2.4 Hz), 9.39 (d, 1H(4.6/5.6), J = 2.4 Hz) [Example 11]
(2-Isopropylphenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-12) 1: 4.6 combination (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ1.06 (d, 6H (1 / 5.6), J = 6.9 Hz), 1.24 (d, 6H (4.6 / 5.6), J = 6.9 Hz), 2.78 (hep, 1H (4.6 / 5.6), J = 6.9 Hz), 3.05 (hep, 1H (1 / 5.6), J = 6.9Hz), 4.02 (s, 3H (4.6 / 5.6)), 4.07 (s, 3H (1 / 5.6)), 7.2-8.2 (m, 9H), 9.16 (d, 1H (1 / 5.6), J = 2.4 Hz), 9.39 (d, 1H (4.6 / 5.6), J = 2.4 Hz)
［実施例１２］
(1,1'-biphenyl)-2-yl-3-quinolinyl-methanone O-methyloximeの製造（化合物番号Ａ３－１７）
　０．５ｇ（１．４７ｍｍｏｌ）の化合物１をＴＨＦ－水混合溶液（１：１）２０ｍＬに溶解し、窒素雰囲気下にPd(PPh3)4を０．１７ｇ（０．１４７ｍｍｏｌ）、フェニルボロン酸を０．２７ｇ（２．２１ｍｍｏｌ）、炭酸カリウムを０．３ｇ（２．２１ｍｍｏｌ）加え、一晩加熱還流を行った。反応液を水に注ぎ、酢酸エチルで抽出し、水洗後硫酸マグネシウムで乾燥した。溶媒を減圧下留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒;ｎ－ヘキサン:酢酸エチル＝９：１）で精製し目的物０．２４ｇを得た。
1:2.2 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ3.88 (s, 3H(2.2/3.2)), 4.00 (s, 3H(1/3.2)), 7.0-8.1 (m, 14H), 8.58 (d, 1H(1/3.2), J= 2.1 Hz), 9.10 (d, 1H(2.2/3.2), J = 2.1 Hz) [Example 12]
Production of (1,1'-biphenyl) -2-yl-3-quinolinyl-methanone O-methyloxime (Compound No. A3-17)
0.5 g (1.47 mmol) of Compound 1 is dissolved in 20 mL of a THF-water mixed solution (1: 1), 0.17 g (0.147 mmol) of Pd (PPh 3 ) 4 and phenylboronic acid are added under a nitrogen atmosphere. 0.27 g (2.21 mmol) and potassium carbonate 0.3 g (2.21 mmol) were added, and the mixture was heated to reflux overnight. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent; n-hexane: ethyl acetate = 9: 1) to obtain 0.24 g of the desired product.
1: 2.2 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ3.88 (s, 3H (2.2 / 3.2)), 4.00 (s, 3H (1 / 3.2)), 7.0-8.1 (m, 14H), 8.58 (d, 1H (1 / 3.2), J = 2.1 Hz), 9.10 (d, 1H (2.2 / 3.2), J = 2.1 Hz)
同様にして以下の化合物を製造した。
［実施例１３］
[2-（2-Propenyl）phenyl]-3-quinolinyl-methanone O-methyloxime（化合物番号Ａ３－１３）
1:2.6 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ1.60 (s, 3H(1/3.6)), 1.88 (s, 3H(2.6/3.6)), 4.03 (s, 3H(2.6/3.6)), 4.04 (s, 3H(1/3.6)), 4.8-5.0 (m, 2H), 7.2-8.2 (m, 9H), 9.02(d, 1H(1/3.6), J = 2.1 Hz), 9.27 (d, 1H(2.6/3.6), J = 2.1 Hz) In the same manner, the following compounds were produced.
[Example 13]
[2- (2-Propenyl) phenyl] -3-quinolinyl-methanone O-methyloxime (Compound No. A3-13)
1: 2.6 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ1.60 (s, 3H (1 / 3.6)), 1.88 (s, 3H (2.6 / 3.6)), 4.03 (s, 3H (2.6 / 3.6)), 4.04 ( s, 3H (1 / 3.6)), 4.8-5.0 (m, 2H), 7.2-8.2 (m, 9H), 9.02 (d, 1H (1 / 3.6), J = 2.1 Hz), 9.27 (d, 1H (2.6 / 3.6), J = 2.1 Hz)
［実施例１４］
(2-Methoxyphenyl)-3-quinolinyl-methanone O-methyloximeの製造（化合物番号Ａ３－１４）
　０．２ｇ（０．７６ｍｍｏｌ）の(2-Methoxyphenyl)-3-quinolinyl-methanoneを２０ｍＬのエタノールに溶解し、ヒドロキシルアミン塩酸塩０．１１ｇ（１．５８ｍｍｏｌ）とピリジン０．１２ｇ（１．５ｍｍｏｌ）を加え、７時間加熱還流を行った。反応液を減圧下濃縮し、冷水を加え、飽和炭酸水素ナトリウム溶液で中和した後、酢酸エチルで抽出した。有機層を水洗し、硫酸マグネシウムで乾燥後、溶媒を減圧下留去し、(2-Methoxyphenyl)-3-quinolinyl-methanone oximeの粗結晶０．３１ｇを得た。
　得られた粗結晶０．３１ｇを５ｍＬのＤＭＦに溶解し、氷冷下水素化ナトリウム（６０％oil　dispersion)を加え、１５分間撹拌した後、氷冷下にヨウ化メチル０．１１ｇ（０．７７ｍｍｏｌ）を加え室温で３時間撹拌した。反応液を氷水に注ぎ、酢酸エチルで抽出し、水洗後硫酸マグネシウムで乾燥した。溶媒を減圧下で留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒;ｎ－ヘキサン:酢酸エチル＝９：１）で精製し目的物０．１５ｇを得た。
1:2 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ3.51 (s, 3H(2/3)), 3.72 (s, 3H(1/3)), 4.04 (s, 3H), 6.8-8.2 (m, 7H), 9.06 (d, 1H(2/3), J= 2.4 Hz) , 9.29 (d, 1H(1/3), J = 2.4 Hz) [Example 14]
Production of (2-Methoxyphenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-14)
0.2 g (0.76 mmol) of (2-Methoxyphenyl) -3-quinolinyl-methanone was dissolved in 20 mL of ethanol, 0.11 g (1.58 mmol) of hydroxylamine hydrochloride and 0.12 g (1.5 mmol) of pyridine. And heated under reflux for 7 hours. The reaction mixture was concentrated under reduced pressure, cold water was added, and the mixture was neutralized with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.31 g of crude crystals of (2-Methoxyphenyl) -3-quinolinyl-methanone oxime.
0.31 g of the obtained crude crystals were dissolved in 5 mL of DMF, sodium hydride (60% oil dispersion) was added under ice cooling, stirred for 15 minutes, and then 0.11 g (0. 77 mmol) was added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was poured into ice water, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent; n-hexane: ethyl acetate = 9: 1) to obtain 0.15 g of the desired product.
1: 2 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ3.51 (s, 3H (2/3)), 3.72 (s, 3H (1/3)), 4.04 (s, 3H), 6.8-8.2 (m, 7H ), 9.06 (d, 1H (2/3), J = 2.4 Hz), 9.29 (d, 1H (1/3), J = 2.4 Hz)
［実施例１５］
[2-(3,3-Dimethyl-1-butynyl)phenyl]-3-quinolinyl-methanone O-methyloximeの製造（化合物番号Ａ３－１５）
　（２－ブロモフェニル）－３－キノリニルメタノン０．５ｇ（１．４６ｍｍｏｌ）を１０ｍＬのトリエチルアミンに溶解し、３，３－ジメチル－１－ブチン０．３６ｇ（４．３８ｍｍｏｌ）、PdCl2(PPh3)2 ０．０５ｇ（０．０７ｍｍｏｌ）及びヨウ化銅０．０３ｇ（０．１６ｍｍｏｌ）を加え２日間加熱還流を行った。反応溶液を水に注ぎ、不溶物を濾別した後、酢酸エチルで抽出し、有機層を水洗した。有機層を硫酸マグネシウムで乾燥した後、溶媒を減圧下で留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒;ｎ－ヘキサン:酢酸エチル＝９：１）で精製し目的物０．０５ｇを得た。
1:1.8 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ0.87 (s, 9H(1.8/2.8)), 0.96 (s, 9H(1/2.8)), 4.05 (s, 3H(1/2.8)), 4.08 (s, 3H(1.8/2.8)), 7.2-8.2 (m, 9H), 9.15 (d, 1H(1.8/2.8), J = 2.1Hz) , 9.34 (d, 1H(1/2.8), J = 2.1 Hz) [Example 15]
Production of [2- (3,3-Dimethyl-1-butynyl) phenyl] -3-quinolinyl-methanone O-methyloxime (Compound No. A3-15)
0.5 g (1.46 mmol) of (2-bromophenyl) -3-quinolinylmethanone was dissolved in 10 mL of triethylamine, 0.36 g (4.38 mmol) of 3,3-dimethyl-1-butyne, PdCl 2 0.05 g (0.07 mmol) of (PPh 3 ) 2 and 0.03 g (0.16 mmol) of copper iodide were added and heated under reflux for 2 days. The reaction solution was poured into water, insolubles were filtered off, extracted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent; n-hexane: ethyl acetate = 9: 1) to obtain the desired product 0. 05 g was obtained.
1: 1.8 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ0.87 (s, 9H (1.8 / 2.8)), 0.96 (s, 9H (1 / 2.8)), 4.05 (s, 3H (1 / 2.8)), 4.08 ( s, 3H (1.8 / 2.8)), 7.2-8.2 (m, 9H), 9.15 (d, 1H (1.8 / 2.8), J = 2.1Hz), 9.34 (d, 1H (1 / 2.8), J = 2.1 Hz)
［実施例１６］
(2-Cyanophenyl)-3-quinolinyl-methanone O-benzyloximeの製造（化合物番号Ａ３－１６）
　（２－ブロモフェニル）－３－キノリニルメタノン０．５ｇ（１．４６ｍｍｏｌ）を５ｍＬのＤＭＦに溶解し、Pd(PPh3)4０．１７ｇ（０．１５ｍｍｏｌ）及びシアン化亜鉛０．１７ｇ（１．４６ｍｍｏｌ）を加え８０℃で一晩撹拌した。反応溶液を水に注ぎ、不溶物を濾別した後、酢酸エチルで抽出し、有機層を水洗した。有機層を硫酸マグネシウムで乾燥した後、溶媒を減圧下で留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒;ｎ－ヘキサン:酢酸エチル＝９：１）で精製し目的物０．１ｇを得た。
1:2 mixtures (E, Z)
物性：amorphous
1H NMR (300 MHz, CDCl3) δ4.10 (s, 3H(1/3)), 4.13 (s, 3H(2/3)), 7.3-8.3 (m, 9H),8.97(d, 1H(2/3), J = 2.1 Hz), 9.28 (d, 1H(1/3), J = 2.1 Hz) [Example 16]
Production of (2-Cyanophenyl) -3-quinolinyl-methanone O-benzyloxime (Compound No. A3-16)
0.5 g (1.46 mmol) of (2-bromophenyl) -3-quinolinylmethanone was dissolved in 5 mL of DMF, 0.17 g (0.15 mmol) of Pd (PPh 3 ) 4 and 0.10 g of zinc cyanide. 17 g (1.46 mmol) was added and stirred at 80 ° C. overnight. The reaction solution was poured into water, insolubles were filtered off, extracted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent; n-hexane: ethyl acetate = 9: 1) to obtain the desired product 0. 1 g was obtained.
1: 2 mixtures (E, Z)
Physical property: amorphous
1 H NMR (300 MHz, CDCl 3 ) δ4.10 (s, 3H (1/3)), 4.13 (s, 3H (2/3)), 7.3-8.3 (m, 9H), 8.97 (d, 1H (2/3), J = 2.1 Hz), 9.28 (d, 1H (1/3), J = 2.1 Hz)
　実施例１７～７６の化合物において、(iso)の表示があるもの以外は、E体/Z体のmixtureである。
[実施例１７]
 (2,3-Dichlorophenyl)-(6,7-dihydro-5H-cyclopenta[b]-pyridin-3-yl)-methanone O-methyloxime（化合物番号A1－22）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 4.07 (s, 3H (1.0/3.0)), 4.08 (s, 3H (2.0/3.0)), 7.28-7.94 (m, 6H), 8.03 (d, 1H (1.0/3.0), J = 2.1 Hz), 8.09-8.15 (m, 1H), 8.26 (d, 1H (2.0/3.0), J = 2.1 Hz), 8.58 (m, 1H(2.0/3.0)), 8.77 (d, 1H (1.0/3.0), J = 5.1 Hz), 8.92 (d, 1H (2.0/3.0) J = 2.4 Hz), 9.22 (d, 1H (1.0/3.0), J = 2.1 Hz). In the compounds of Examples 17 to 76, except for those indicated by (iso), they are E / Z mixture.
[Example 17]
(2,3-Dichlorophenyl)-(6,7-dihydro-5H-cyclopenta [b] -pyridin-3-yl) -methanone O-methyloxime (Compound No. A1-22)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 4.07 (s, 3H (1.0 / 3.0)), 4.08 (s, 3H (2.0 / 3.0)), 7.28-7.94 (m, 6H), 8.03 (d, 1H (1.0 / 3.0), J = 2.1 Hz), 8.09-8.15 (m, 1H), 8.26 (d, 1H (2.0 / 3.0), J = 2.1 Hz), 8.58 (m, 1H (2.0 / 3.0)), 8.77 (d, 1H (1.0 / 3.0), J = 5.1 Hz), 8.92 (d, 1H (2.0 / 3.0) J = 2.4 Hz), 9.22 (d, 1H (1.0 / 3.0), J = 2.1 Hz).
[実施例１８]
(2-Bromo-3-chlorophenyl)-(thieno[2,3-b]pyridin-5-yl)-methanone O-methyloxime（化合物番号A1－23）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 2.05-2.20 (m, 2H), 2.90-3.05 (m, 4H), 3.98 (s, 3H (3.0/4.0)), 4.04 (s, 3H (1.0/4.0)), 7.07-7.68 (m, 4H), 8.28-8.30 (m, 1H (3.0/4.0)), 8.41-8.43 (m, 1H (1.0/4.0)). [Example 18]
(2-Bromo-3-chlorophenyl)-(thieno [2,3-b] pyridin-5-yl) -methanone O-methyloxime (Compound No. A1-23)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 2.05-2.20 (m, 2H), 2.90-3.05 (m, 4H), 3.98 (s, 3H (3.0 / 4.0)), 4.04 (s, 3H (1.0 / 4.0)), 7.07-7.68 (m, 4H), 8.28-8.30 (m, 1H (3.0 / 4.0)), 8.41-8.43 (m, 1H (1.0 / 4.0)).
[実施例１９]
(2-Pyridinyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－1）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 4.07 (s, 3H (1.0/3.0)), 4.08 (s, 3H (2.0/3.0)), 7.28-7.94 (m, 6H), 8.03 (d, 1H (1.0/3.0), J = 2.1 Hz), 8.09-8.15 (m, 1H), 8.26 (d, 1H (2.0/3.0), J = 2.1 Hz), 8.58 (m, 1H(2.0/3.0)), 8.77 (d, 1H (1.0/3.0), J = 5.1 Hz), 8.92 (d, 1H (2.0/3.0) J = 2.4 Hz), 9.22 (d, 1H (1.0/3.0), J = 2.1 Hz). [Example 19]
(2-Pyridinyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-1)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 4.07 (s, 3H (1.0 / 3.0)), 4.08 (s, 3H (2.0 / 3.0)), 7.28-7.94 (m, 6H), 8.03 (d, 1H (1.0 / 3.0), J = 2.1 Hz), 8.09-8.15 (m, 1H), 8.26 (d, 1H (2.0 / 3.0), J = 2.1 Hz), 8.58 (m, 1H (2.0 / 3.0)), 8.77 (d, 1H (1.0 / 3.0), J = 5.1 Hz), 8.92 (d, 1H (2.0 / 3.0) J = 2.4 Hz), 9.22 (d, 1H (1.0 / 3.0), J = 2.1 Hz).
[実施例２０]
(3-Pyridinyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－6）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 4.05 (s, 3H (1.0/2.3)), 4.07 (s, 3H (1.3/2.3)), 7.31 (m, 1H (1.0/2.3)), 7.44 (m, 1H (1.3/2.3)), 7.52-7.86 (m, 4H), 7.44 (d, 1H (1.3/2.3), J = 1.8 Hz), 8.11-8.18 (m, 1H+1H (1.0/2.3)), 8.64-8.77 (m, 2H), 8.95 (d, 1H (1.0/2.3), J = 2.1 Hz), 9.28 (d, 1H (1.3/2.3), J = 2.1 Hz). [Example 20]
(3-Pyridinyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-6)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 4.05 (s, 3H (1.0 / 2.3)), 4.07 (s, 3H (1.3 / 2.3)), 7.31 (m, 1H (1.0 / 2.3)), 7.44 ( m, 1H (1.3 / 2.3)), 7.52-7.86 (m, 4H), 7.44 (d, 1H (1.3 / 2.3), J = 1.8 Hz), 8.11-8.18 (m, 1H + 1H (1.0 / 2.3) ), 8.64-8.77 (m, 2H), 8.95 (d, 1H (1.0 / 2.3), J = 2.1 Hz), 9.28 (d, 1H (1.3 / 2.3), J = 2.1 Hz).
[実施例２１]
(4-Pyridinyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－9）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 4.06 (s, 3H), 7.30 (m, 2H (1.0/2.0)), 7.43 (m, 2H (1.0/2.0)), 7.52-7.89 (m, 3H+1H (1.0/2.0)), 8.11-8.18 (m, 1H+1H (1.0/2.0)), 8.63 (dd, 2H (1.0/2.0), J = 1.5, 4.8 Hz), 8.78 (dd, 2H (1.0/2.0), J = 1.5, 4.5 Hz), 8.90 (d, 1H (1.0/2.0), J = 2.1 Hz), 9.27 (d, 1H (1.0/2.0), J = 2.1 Hz). [Example 21]
(4-Pyridinyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-9)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 4.06 (s, 3H), 7.30 (m, 2H (1.0 / 2.0)), 7.43 (m, 2H (1.0 / 2.0)), 7.52-7.89 (m, 3H + 1H (1.0 / 2.0)), 8.11-8.18 (m, 1H + 1H (1.0 / 2.0)), 8.63 (dd, 2H (1.0 / 2.0), J = 1.5, 4.8 Hz), 8.78 (dd, 2H ( 1.0 / 2.0), J = 1.5, 4.5 Hz), 8.90 (d, 1H (1.0 / 2.0), J = 2.1 Hz), 9.27 (d, 1H (1.0 / 2.0), J = 2.1 Hz).
[実施例２２]
(3-Quinolinyl)-2-thiophenyl-methanone O-methyloxime（化合物番号A2－12）
物性：viscous oil
1H-NMR (300 MHz, CDCl3) δ 4.06 (s, 3H), 7.30 (m, 1H (1/2)), 7.43 (m, 1H (1/2), 7.52-7.88 (m, 6H), 8.15-8.21 (m, 1H+1H (1.0/2.2)), 8.33 (d, 1H (1.2/2.2), J = 2.1 Hz), 8.96 (d, 1H (1.0/2.2), J = 2.1 Hz), 9.07 (d, 1H (1.2/2.2), J = 2.1 Hz). [Example 22]
(3-Quinolinyl) -2-thiophenyl-methanone O-methyloxime (Compound No. A2-12)
Physical properties: viscoous oil
1 H-NMR (300 MHz, CDCl 3 ) δ 4.06 (s, 3H), 7.30 (m, 1H (1/2)), 7.43 (m, 1H (1/2), 7.52-7.88 (m, 6H) , 8.15-8.21 (m, 1H + 1H (1.0 / 2.2)), 8.33 (d, 1H (1.2 / 2.2), J = 2.1 Hz), 8.96 (d, 1H (1.0 / 2.2), J = 2.1 Hz) , 9.07 (d, 1H (1.2 / 2.2), J = 2.1 Hz).
[実施例２３]
(3-Quinolinyl)-3-thiophenyl-methanone O-methyloxime（化合物番号A2－13）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ3.97 (s, 3H 3/5), 4.12 (s, 3H 2/5), 7.15-7.87 (m, 6H), 8.14-8.20 (m, 2H), 8.95 (d, 1H 3/5), 9.14 (d, 1H 2/5). [Example 23]
(3-Quinolinyl) -3-thiophenyl-methanone O-methyloxime (Compound No. A2-13)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ3.97 (s, 3H 3/5), 4.12 (s, 3H 2/5), 7.15-7.87 (m, 6H), 8.14-8.20 (m, 2H) , 8.95 (d, 1H 3/5), 9.14 (d, 1H 2/5).
[実施例２４]
(2-Furanyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－14）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ4.02 (s, 3H 1/2), 4.19 (s, 3H 1/2), 6.45 (m, 1H 1/2), 6.62 (m, 1H 1/2), 7.47-7.89 (m, 5H), 8.15 (s, 1H 1/2), 8.17 (s, 1H 1/2), 8.23 (s, 1H 1/2), 8.39 (s, 1H 1/2), 8.97 (br, 1H 1/2), 9.11(br, 1H 1/2) [Example 24]
(2-Furanyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-14)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ4.02 (s, 3H 1/2), 4.19 (s, 3H 1/2), 6.45 (m, 1H 1/2), 6.62 (m, 1H 1 / 2), 7.47-7.89 (m, 5H), 8.15 (s, 1H 1/2), 8.17 (s, 1H 1/2), 8.23 (s, 1H 1/2), 8.39 (s, 1H 1/2) ), 8.97 (br, 1H 1/2), 9.11 (br, 1H 1/2)
[実施例２５]
(3-Furanyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－15）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 3.96 (s, 3H 1/2), 4.15 (s, 3H, 1/2), 6.56 (m, 1H 1/2), 6.82 (m, 1H, 1/2), 7.27-8.16 (m, 6H), 8.20 (d, 1H 1/2), 8.29 (d, 1H, 1/2), 8.96 (br, 1H 1/2), 9.10 (br, 1H, 1/2). [Example 25]
(3-Furanyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-15)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 3.96 (s, 3H 1/2), 4.15 (s, 3H, 1/2), 6.56 (m, 1H 1/2), 6.82 (m, 1H, 1 / 2), 7.27-8.16 (m, 6H), 8.20 (d, 1H 1/2), 8.29 (d, 1H, 1/2), 8.96 (br, 1H 1/2), 9.10 (br, 1H, 1/2).
[実施例２６]
(3-Quinolinyl)-2-thiazolyl-methanone O-methyloxime（化合物番号A2－16）
物性：m. p. 88-93 ℃ [Example 26]
(3-Quinolinyl) -2-thiazolyl-methanone O-methyloxime (Compound No. A2-16)
Physical properties: m. P. 88-93 ℃
[実施例２７]
(1-Imidazolyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－17）
物性：m. p. 95-98 ℃ [Example 27]
(1-Imidazolyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-17)
Physical properties: m. P. 95-98 ℃
[実施例２８]
(4,5-Dichloroimidazol-1-yl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－18）
物性：m. p. 225-227 ℃ [Example 28]
(4,5-Dichloroimidazol-1-yl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-18)
Physical properties: m. P. 225-227 ℃
[実施例２９]
(2-Isopropylimidazol-1-yl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－19）
物性：m. p. 155-157 ℃ [Example 29]
(2-Isopropylimidazol-1-yl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-19)
Physical properties: m. P. 155-157 ℃
[実施例３０]
(1-Pyrazolyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－20）
物性：m. p. 105-107 ℃ [Example 30]
(1-Pyrazolyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-20)
Physical properties: m. P. 105-107 ℃
[実施例３１]
(2-Methyl-2H-pyrazol-3-yl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－21）
物性：m. p. 140-151 ℃ [Example 31]
(2-Methyl-2H-pyrazol-3-yl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-21)
Physical properties: m. P. 140-151 ℃
[実施例３２]
(1-Pyrrolidinyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－22）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 1.82-1.94 (m, 4H), 3.18-3.22 (m, 4H), 3.66 (s, 3H), 7.55 (t, 3H), 7.74 (t, 1H), 7.85 (d, 1H), 8.12 (d, 1H), 8.13 (s, 1H), 8.85 (s, 1H). [Example 32]
(1-Pyrrolidinyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-22)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 1.82-1.94 (m, 4H), 3.18-3.22 (m, 4H), 3.66 (s, 3H), 7.55 (t, 3H), 7.74 (t, 1H) , 7.85 (d, 1H), 8.12 (d, 1H), 8.13 (s, 1H), 8.85 (s, 1H).
[実施例３３]
(1-Piperidinyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－23）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ1.60-1.64 (br, 6H), 3.08 (br, 4H), 3.70 (s, 3H), 7.58 (t, 1H), 7.75 (t, 1H), 7.85 (d, 1H), 8.12 (d, 1H), 8.18 (s, 1H), 8.89 (s, 1H). [Example 33]
(1-Piperidinyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-23)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ1.60-1.64 (br, 6H), 3.08 (br, 4H), 3.70 (s, 3H), 7.58 (t, 1H), 7.75 (t, 1H), 7.85 (d, 1H), 8.12 (d, 1H), 8.18 (s, 1H), 8.89 (s, 1H).
[実施例３４]
 (1-Piperidinyl)-3-quinolinyl-methanone O-ethyloxime（化合物番号A2－24）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ1.16 (t, 3H), 1.59 (br, 6H), 3.07 (br, 4H), 3.98 (q, 2H), 7.56 (t, 1H), 7.75 (t, 1H), 7.86 (d, 1H), 8.12 (d, 1H), 8.19 (s, 1H), 8.92 (s, 1H). [Example 34]
(1-Piperidinyl) -3-quinolinyl-methanone O-ethyloxime (Compound No. A2-24)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ1.16 (t, 3H), 1.59 (br, 6H), 3.07 (br, 4H), 3.98 (q, 2H), 7.56 (t, 1H), 7.75 ( t, 1H), 7.86 (d, 1H), 8.12 (d, 1H), 8.19 (s, 1H), 8.92 (s, 1H).
[実施例３５]
(1-Piperidinyl)-3-quinolinyl-methanone O-isopropyloxime（化合物番号A2－25）
物性：m. p. 51-53 ℃ [Example 35]
(1-Piperidinyl) -3-quinolinyl-methanone O-isopropyloxime (Compound No. A2-25)
Physical properties: m. P. 51-53 ℃
[実施例３６]
(1-Piperidinyl)-3-quinolinyl-methanone O-sec-butyloxime（化合物番号A2－26）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 0.82 (t, 3H), 1.14 (d, 3H), 1.31 (m, 2H), 1.60 (br, 6H), 3.06 (br, 4H), 3.97 (m, 1H), 7.56 (t, 1H), 7.74 (t, 1H), 7.84 (d, 1H), 8.12 (d, 1H), 8.21 (s, 1H), 8.96 (s, 1H). [Example 36]
(1-Piperidinyl) -3-quinolinyl-methanone O-sec-butyloxime (Compound No. A2-26)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 0.82 (t, 3H), 1.14 (d, 3H), 1.31 (m, 2H), 1.60 (br, 6H), 3.06 (br, 4H), 3.97 (m , 1H), 7.56 (t, 1H), 7.74 (t, 1H), 7.84 (d, 1H), 8.12 (d, 1H), 8.21 (s, 1H), 8.96 (s, 1H).
[実施例３７]
(1-Piperidinyl)-3-quinolinyl-methanone O-benzyloxime（化合物番号A2－27）
物性：m. p. 93-95 ℃ [Example 37]
(1-Piperidinyl) -3-quinolinyl-methanone O-benzyloxime (Compound No. A2-27)
Physical properties: m. P. 93-95 ℃
[実施例３８]
(1-Piperidinyl)-3-quinolinyl-methanone O-acetyloxime（化合物番号A2－28）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ1.64 (br, 6H), 1.84 (s, 3H), 3.30 (br, 4H), 7.64 (t, 1H), 7.82 (t, 1H), 7.88 (d, 1H), 8.12 (d, 1H), 8.16 (d, 1H), 8.82 (d, 1H). [Example 38]
(1-Piperidinyl) -3-quinolinyl-methanone O-acetyloxime (Compound No. A2-28)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ1.64 (br, 6H), 1.84 (s, 3H), 3.30 (br, 4H), 7.64 (t, 1H), 7.82 (t, 1H), 7.88 ( d, 1H), 8.12 (d, 1H), 8.16 (d, 1H), 8.82 (d, 1H).
[実施例３９]
(1-Piperidinyl)-3-quinolinyl-methanone O-benzoyloxime（化合物番号A2－29）
物性：m. p. 169-171 ℃ [Example 39]
(1-Piperidinyl) -3-quinolinyl-methanone O-benzoyloxime (Compound No. A2-29)
Physical properties: m. P. 169-171 ℃
[実施例４０]
(1-Naphthalenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－30）
物性：m. p. 154-168 ℃ [Example 40]
(1-Naphthalenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-30)
Physical properties: m. P. 154-168 ℃
[実施例４１]
(8-Quinolinyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A2－31）
物性：m. p. 154-168 ℃ [Example 41]
(8-Quinolinyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A2-31)
Physical properties: m. P. 154-168 ℃
[実施例４２]
(3,5-Dichlorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－18）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 4.03 (s, 3H (1/2)), 4.06 (s, 3H, (1/2)), 7.26-7.93 (m, 6H+1H(1/2)), 8.11-8.18 (m, 1H+1H(1/2)), 8.87 (d, 1H (1/2), J = 1.8 Hz), 9.23 (d, 1H (1/2), J = 2.1 Hz). [Example 42]
(3,5-Dichlorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-18)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 4.03 (s, 3H (1/2)), 4.06 (s, 3H, (1/2)), 7.26-7.93 (m, 6H + 1H (1/2 )), 8.11-8.18 (m, 1H + 1H (1/2)), 8.87 (d, 1H (1/2), J = 1.8 Hz), 9.23 (d, 1H (1/2), J = 2.1 Hz).
[実施例４３]
(2-Bromo-3-chlorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－19(mix)）
物性：m. p. 146-148 ℃ [Example 43]
(2-Bromo-3-chlorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-19 (mix))
Physical properties: m. P. 146-148 ℃
[実施例４４]
(2-Bromo-3-chlorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－19(iso)）
物性：m. p. 169-171 ℃ [Example 44]
(2-Bromo-3-chlorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-19 (iso))
Physical properties: m. P. 169-171 ℃
[実施例４５]
(3-Chloro-2-isopropenylphenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－20）
物性：m. p. 150-152 ℃ [Example 45]
(3-Chloro-2-isopropenylphenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-20)
Physical properties: m. P. 150-152 ℃
[実施例４６]
 (3-Chloro-2-cyanophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－21）
物性：m. p. 138-140 ℃ [Example 46]
(3-Chloro-2-cyanophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-21)
Physical properties: m. P. 138-140 ℃
[実施例４７]
(3-Chloro-2-methylphenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－22）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 2.22 (s, 3H (1/2)), 2.23 (s, 3H (1/2)), 4.02 (s, 3H (1/2)), 4.08 (s, 3H, (1/2)), 7.04 (d, 1H (1/2), J = 7.5 Hz), 7.19-7.79 (m, 6H), 8.09-8.20 (m, 1H+1H(1/2)), 9.13 (d, 1H (1/2), J = 2.4 Hz), 9.37 (d, 1H (1/2), J = 2.1 Hz). [Example 47]
(3-Chloro-2-methylphenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-22)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 2.22 (s, 3H (1/2)), 2.23 (s, 3H (1/2)), 4.02 (s, 3H (1/2)), 4.08 ( s, 3H, (1/2)), 7.04 (d, 1H (1/2), J = 7.5 Hz), 7.19-7.79 (m, 6H), 8.09-8.20 (m, 1H + 1H (1/2 )), 9.13 (d, 1H (1/2), J = 2.4 Hz), 9.37 (d, 1H (1/2), J = 2.1 Hz).
[実施例４８]
(3-Chloro-2-methylphenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－23）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 3.78 (s, 3H (1/2)), 3.90 (s, 3H (1/2)), 6.40 (d, 1H (1/2), J = 7.8 Hz), 6.67 (d, 1H (1/2), J = 7.8 Hz), 6.77-6.93 (m, 1H), 7.02-7.16 (m, 2H), 7.29-7.73 (m, 6H), 7.82-7.88 (m, 1H), 8.03-8.10 (m, 1H), 8.78 (d, 1H (1/2), J = 2.1 Hz), 9.12 (d, 1H (1/2), J = 2.1 Hz). [Example 48]
(3-Chloro-2-methylphenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-23)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 3.78 (s, 3H (1/2)), 3.90 (s, 3H (1/2)), 6.40 (d, 1H (1/2), J = 7.8 Hz), 6.67 (d, 1H (1/2), J = 7.8 Hz), 6.77-6.93 (m, 1H), 7.02-7.16 (m, 2H), 7.29-7.73 (m, 6H), 7.82-7.88 (m, 1H), 8.03-8.10 (m, 1H), 8.78 (d, 1H (1/2), J = 2.1 Hz), 9.12 (d, 1H (1/2), J = 2.1 Hz).
[実施例４９]
(2-Benzyl-3-chlorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－24）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 3.86 (s, 3H), 3.96-4.14 (m, 2H), 6.87 (m, 1H), 6.97-7.70 (m, 11H) 8.05 (dd, 1H, J = 0.9, 8.4 Hz), 9.22 (d, 1H, J = 2.1 Hz). [Example 49]
(2-Benzyl-3-chlorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-24)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 3.86 (s, 3H), 3.96-4.14 (m, 2H), 6.87 (m, 1H), 6.97-7.70 (m, 11H) 8.05 (dd, 1H, J = 0.9, 8.4 Hz), 9.22 (d, 1H, J = 2.1 Hz).
[実施例５０]
[2-(3,4-Dichlorobenzyloxy)-phenyl]-3-quinolinyl-methanone O-methyloxime（化合物番号A3－25）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ4.05 (s, 3H 2/5), 4.06 (s, 3H, 3/5), 4.71 (s, 2H 2/5), 4.96 (s, 2H, 3/5), 6.41 (dd, 1H 2/5), 6.84 (dd, 1H, 3/5), 6.87-7.77 (m, 9H), 7.95 (d, 1H 3/5), 8.05-8.12 (m, 1H), 8.21 (d, 1H 2/5), 8.91 (d, 1H 2/5), 9.25 (d, 1H 3/5). [Example 50]
[2- (3,4-Dichlorobenzyloxy) -phenyl] -3-quinolinyl-methanone O-methyloxime (Compound No. A3-25)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ4.05 (s, 3H 2/5), 4.06 (s, 3H, 3/5), 4.71 (s, 2H 2/5), 4.96 (s, 2H, 3/5), 6.41 (dd, 1H 2/5), 6.84 (dd, 1H, 3/5), 6.87-7.77 (m, 9H), 7.95 (d, 1H 3/5), 8.05-8.12 (m , 1H), 8.21 (d, 1H 2/5), 8.91 (d, 1H 2/5), 9.25 (d, 1H 3/5).
[実施例５１]
(2,3-Dichlorophenyl)-(8-fluoroquinolin-3-yl)-methanone O-methyloxime（化合物番号A3－26）
物性：m. p. 147-149 ℃ [Example 51]
(2,3-Dichlorophenyl)-(8-fluoroquinolin-3-yl) -methanone O-methyloxime (Compound No. A3-26)
Physical properties: m. P. 147-149 ℃
[実施例５２]
(3-Fluorophenyl)-3-quinolinyl-methanone O-acethyloxime（化合物番号A3－27）
物性：m. p. 108-112 ℃ [Example 52]
(3-Fluorophenyl) -3-quinolinyl-methanone O-acethyloxime (Compound No. A3-27)
Physical properties: m. P. 108-112 ℃
[実施例５３]
(3-Fluorophenyl)-(8-fluoroquinolin-3-yl)-methanone O-acethyloxime（化合物番号A3－28）
物性：m. p. 124-126 ℃ [Example 53]
(3-Fluorophenyl)-(8-fluoroquinolin-3-yl) -methanone O-acethyloxime (Compound No. A3-28)
Physical properties: m. P. 124-126 ℃
[実施例５４]
(3-Fluorophenyl)-3-quinolinyl-methanone O-benzoyloxime（化合物番号A3－29）
物性：m. p. 155-158 ℃ [Example 54]
(3-Fluorophenyl) -3-quinolinyl-methanone O-benzoyloxime (Compound No. A3-29)
Physical properties: m. P. 155-158 ℃
[実施例５５]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-benzyloxime（化合物番号A3－30）
物性：m. p. 125-127 ℃ [Example 55]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-benzyloxime (Compound No. A3-30)
Physical properties: m. P. 125-127 ℃
[実施例５６]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-(4-chlorobenzyl)-oxime（化合物番号A3－31）
物性：m. p. 153-155 ℃ [Example 56]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O- (4-chlorobenzyl) -oxime (Compound No. A3-31)
Physical properties: m. P. 153-155 ℃
[実施例５７]
(2-Bromo-3-chlorophenyl)-3-quinolinyl-methanone O-(2-methylallyl)-oxime（化合物番号A3－32）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 1.76 (s, 3H (5/6)), 1.82 (s, 3H, (1/6)), 4.67 (s, 2H (5/6)), 4.72 (s, 2H, (1/6)), 4.98 (m, 2H), 7.14 (m, 1H), 7.38-7.81 (m, 6H), 8.11 (d, 1H (5/6), J = 7.8 Hz), 8.17 (d, 1H (1/6), J = 2.4 Hz), 9.23 (d, 1H, (1/6), J = 2.1 Hz), 9.35 (d, 1H (5/6), J = 2.4 Hz). [Example 57]
(2-Bromo-3-chlorophenyl) -3-quinolinyl-methanone O- (2-methylallyl) -oxime (Compound No. A3-32)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 1.76 (s, 3H (5/6)), 1.82 (s, 3H, (1/6)), 4.67 (s, 2H (5/6)), 4.72 (s, 2H, (1/6)), 4.98 (m, 2H), 7.14 (m, 1H), 7.38-7.81 (m, 6H), 8.11 (d, 1H (5/6), J = 7.8 Hz ), 8.17 (d, 1H (1/6), J = 2.4 Hz), 9.23 (d, 1H, (1/6), J = 2.1 Hz), 9.35 (d, 1H (5/6), J = 2.4 Hz).
[実施例５８]
(2-Bromo-3-chlorophenyl)-(8-fluoroquinolin-3-yl)-methanone O-methyloxime（化合物番号A3－33）
物性：m. p. 138-140 ℃ [Example 58]
(2-Bromo-3-chlorophenyl)-(8-fluoroquinolin-3-yl) -methanone O-methyloxime (Compound No. A3-33)
Physical properties: m. P. 138-140 ℃
[実施例５９]
[3-Chloro-2-(2-methylpropenyl)phenyl]-(8-fluoroquinolin-3-yl)-methanone O-methyloxime（化合物番号A3－34）
物性：m. p. 104-106 ℃ [Example 59]
[3-Chloro-2- (2-methylpropenyl) phenyl]-(8-fluoroquinolin-3-yl) -methanone O-methyloxime (Compound No. A3-34)
Physical properties: m. P. 104-106 ℃
[実施例６０]
(3-Chloro-2-cyanophenyl)-(8-fluoroquinolin-3-yl)-methanone O-methyloxime（化合物番号A3－35）
物性：m. p. 158-160 ℃ [Example 60]
(3-Chloro-2-cyanophenyl)-(8-fluoroquinolin-3-yl) -methanone O-methyloxime (Compound No. A3-35)
Physical properties: m. P. 158-160 ℃
[実施例６１]
(2,3-Dicyanophenyl)-(8-fluoroquinolin-3-yl)-methanone O-methyloxime（化合物番号A3－36）
物性：m. p. 172-174 ℃ [Example 61]
(2,3-Dicyanophenyl)-(8-fluoroquinolin-3-yl) -methanone O-methyloxime (Compound No. A3-36)
Physical properties: m. P. 172-174 ℃
[実施例６２]
[3-Chloro-2-(2-methylpropenyl)phenyl]-(8-fluoroquinolin-3-yl)-methanone O-methyloxime（化合物番号A3－37(mix)）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 1.30-1.62 (m, 6H), 4.02 (s, 3H (3.0/4.0)), 4.30 (s, 3H, (1/4.0)), 7.2-7.6 (m, 6H), 7.80 (t, 1H (3.0/4.0), J = 1.8 Hz), 7.89(d, 1H (1.0/4.0), J = 1.8 Hz), 8.95 (d, 1H (1.0/4.0), J = 1.8 Hz), 9.21 (d, 1H (3.0/4.0), J = 1.8 Hz). [Example 62]
[3-Chloro-2- (2-methylpropenyl) phenyl]-(8-fluoroquinolin-3-yl) -methanone O-methyloxime (Compound No. A3-37 (mix))
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 1.30-1.62 (m, 6H), 4.02 (s, 3H (3.0 / 4.0)), 4.30 (s, 3H, (1 / 4.0)), 7.2-7.6 ( m, 6H), 7.80 (t, 1H (3.0 / 4.0), J = 1.8 Hz), 7.89 (d, 1H (1.0 / 4.0), J = 1.8 Hz), 8.95 (d, 1H (1.0 / 4.0), J = 1.8 Hz), 9.21 (d, 1H (3.0 / 4.0), J = 1.8 Hz).
[実施例６３]
[3-Chloro-2-(2-methylpropenyl)phenyl]-(8-fluoroquinolin-3-yl)-methanone O-methyloxime（化合物番号A3－37(iso)）
物性：m. p. 104-106 ℃ [Example 63]
[3-Chloro-2- (2-methylpropenyl) phenyl]-(8-fluoroquinolin-3-yl) -methanone O-methyloxime (Compound No. A3-37 (iso))
Physical properties: m. P. 104-106 ℃
[実施例６４]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-(2-chlorobenzyl)oxime（化合物番号A3－40）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 5.40 (s, 2H (4.6/5.6)), 5.45 (s, 2H, (1/5.6)), 7.17-7.81 (m, 11H), 8.10 (d, 1H (4.6/5.6), J = 8.4 Hz), 8.22(d, 1H (1/5.6), J = 1.8 Hz), 9.19 (d, 1H (1/5.6), J = 2.1 Hz), 9.32 (d, 1H (4.6/5.6), J = 2.1 Hz). [Example 64]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O- (2-chlorobenzyl) oxime (Compound No. A3-40)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 5.40 (s, 2H (4.6 / 5.6)), 5.45 (s, 2H, (1 / 5.6)), 7.17-7.81 (m, 11H), 8.10 (d, 1H (4.6 / 5.6), J = 8.4 Hz), 8.22 (d, 1H (1 / 5.6), J = 1.8 Hz), 9.19 (d, 1H (1 / 5.6), J = 2.1 Hz), 9.32 (d , 1H (4.6 / 5.6), J = 2.1 Hz).
[実施例６５]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-(3-chlorobenzyl)oxime（化合物番号A3－41）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 5.24 (s, 2H (4/5)), 5.29 (s, 2H, (1/5)), 7.13-7.79 (m, 11H), 8.09-8.15 (s, 1H), 9.15 (d, 1H (1/5), J = 2.4 Hz), 9.31 (d, 1H (4/5), J = 2.1Hz). [Example 65]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O- (3-chlorobenzyl) oxime (Compound No. A3-41)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 5.24 (s, 2H (4/5)), 5.29 (s, 2H, (1/5)), 7.13-7.79 (m, 11H), 8.09-8.15 ( s, 1H), 9.15 (d, 1H (1/5), J = 2.4 Hz), 9.31 (d, 1H (4/5), J = 2.1 Hz).
[実施例６６]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-allyloxime（化合物番号A3－42）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 4.75-4.81 (m, 2H), 5.20-5.34 (m, 2H), 5.98-6.07 (m, 1H), 7.18 (dd, 1H (3.8/4.8), J = 1.5, 7.8 Hz), 7.34-7.82 (m, 6H), 8.09-8.13 (m, 1H+1H (1.0/4.8)), 9.34 (d, 1H (3.8/4.8), J = 2.4 Hz). [Example 66]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-allyloxime (Compound No. A3-42)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 4.75-4.81 (m, 2H), 5.20-5.34 (m, 2H), 5.98-6.07 (m, 1H), 7.18 (dd, 1H (3.8 / 4.8), J = 1.5, 7.8 Hz), 7.34-7.82 (m, 6H), 8.09-8.13 (m, 1H + 1H (1.0 / 4.8)), 9.34 (d, 1H (3.8 / 4.8), J = 2.4 Hz).
[実施例６７]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-(2-propynyl)oxime（化合物番号A3－43）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 2.50 (t, 1H (4.2/5.2), J = 2.4 Hz), 2.54 (t, 1H (1.0/5.2), J = 2.4 Hz), 4.84 (d, 1H (4.2/5.2), J = 2.4 Hz), 4.88(d, 1H (4.2/5.2), J = 2.4 Hz), 7.18-7.87 (m, 6H+1H (4.2/5.2), 8.10-8.18 (m, 1H+1H (1.0/5.2)), 9.13 (d, 1H (1.0/5.2), J = 2.1 Hz), 9.34 (d, 1H (4.2/5.2), J = 2.1 Hz). [Example 67]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O- (2-propynyl) oxime (Compound No. A3-43)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 2.50 (t, 1H (4.2 / 5.2), J = 2.4 Hz), 2.54 (t, 1H (1.0 / 5.2), J = 2.4 Hz), 4.84 (d, 1H (4.2 / 5.2), J = 2.4 Hz), 4.88 (d, 1H (4.2 / 5.2), J = 2.4 Hz), 7.18-7.87 (m, 6H + 1H (4.2 / 5.2), 8.10-8.18 (m , 1H + 1H (1.0 / 5.2)), 9.13 (d, 1H (1.0 / 5.2), J = 2.1 Hz), 9.34 (d, 1H (4.2 / 5.2), J = 2.1 Hz).
[実施例６８]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-ethyloxime（化合物番号A3－44）
物性：m. p. 110-112 ℃ [Example 68]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-ethyloxime (Compound No. A3-44)
Physical properties: m. P. 110-112 ℃
[実施例６９]
 (2,3-Dichlorophenyl)-3-quinolinyl-methanone O-isobutyloxime（化合物番号A3－45）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 0.90 (d, 3H (1/2), J = 6.6 Hz), 0.99 (d, 1H (1/2), J = 6.6 Hz), 1.99-2.16 (m, 1H), 4.04(d, 2H (1/2), J = 6.9 Hz), 4.08 (d, 2H, J = 6.9 Hz), 7.17 (dd, 1H (1/2), J= 1.8, 7.8 Hz), 7.32-7.81 (m, 6H+1H (1/2)), 8.10-8.16 (m, 1H+1H (1/2)), 9.20 (d, 1H (1/2), J = 2.1 Hz), 9.34 (d, 1H (1/2), J = 2.1 Hz). [Example 69]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-isobutyloxime (Compound No. A3-45)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 0.90 (d, 3H (1/2), J = 6.6 Hz), 0.99 (d, 1H (1/2), J = 6.6 Hz), 1.99-2.16 ( m, 1H), 4.04 (d, 2H (1/2), J = 6.9 Hz), 4.08 (d, 2H, J = 6.9 Hz), 7.17 (dd, 1H (1/2), J = 1.8, 7.8 Hz), 7.32-7.81 (m, 6H + 1H (1/2)), 8.10-8.16 (m, 1H + 1H (1/2)), 9.20 (d, 1H (1/2), J = 2.1 Hz ), 9.34 (d, 1H (1/2), J = 2.1 Hz).
[実施例７０]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-isopropyloxime（化合物番号A3－46）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 1.29 (d, 3H (5.2/6.2), J = 6.3 Hz), 1.36 (d, 1H (1.0/6.2), J = 6.3 Hz), 4.53-4.61 (m, 1H), 7.13-7.78 (m, 6H+1H (5.2/6.2)), 8.09-8.12 (m, 1H+1H (1.0/6.2)), 9.25 (d, 1H (1.0/6.2), J = 2.4 Hz), 9.37 (d, 1H (5.2/6.2), J = 2.4 Hz). [Example 70]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-isopropyloxime (Compound No. A3-46)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 1.29 (d, 3H (5.2 / 6.2), J = 6.3 Hz), 1.36 (d, 1H (1.0 / 6.2), J = 6.3 Hz), 4.53-4.61 ( m, 1H), 7.13-7.78 (m, 6H + 1H (5.2 / 6.2)), 8.09-8.12 (m, 1H + 1H (1.0 / 6.2)), 9.25 (d, 1H (1.0 / 6.2), J = 2.4 Hz), 9.37 (d, 1H (5.2 / 6.2), J = 2.4 Hz).
[実施例７１]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-cyclopropylmethyloxime（化合物番号A3－47）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 0.31-0.37 (m, 2H), 0.53-0.62 (m, 2H), 1.21-1.26 (m, 1H), 4.07-4.14 (m, 2H), 7.18 (dd, 1H (2/3), J = 1.5, 7.5 Hz), 7.33-7.79 (m, 6H), 8.10-8.14 (m, 1H+1H (1/3)), 9.25 (d, 1H (1/3), J = 2.1 Hz), 9.37 (d, 1H (2/3), J = 2.1 Hz). [Example 71]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-cyclopropylmethyloxime (Compound No. A3-47)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 0.31-0.37 (m, 2H), 0.53-0.62 (m, 2H), 1.21-1.26 (m, 1H), 4.07-4.14 (m, 2H), 7.18 ( dd, 1H (2/3), J = 1.5, 7.5 Hz), 7.33-7.79 (m, 6H), 8.10-8.14 (m, 1H + 1H (1/3)), 9.25 (d, 1H (1 / 3), J = 2.1 Hz), 9.37 (d, 1H (2/3), J = 2.1 Hz).
[実施例７２]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-(2-methylallyl)oxime（化合物番号A3－49）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 1.78 (s, 3H (1.1/2.1)), 1.81 (s, 3H (1/2.1)), 4.68 (s, 2H (1.1/2.1)), 4.72 (s, 2H (1/2.1)), 4.92-4.97 (m, 2H), 7.18-7.81 (m, 6H+1H (1.1/2.1)), 8.09-8.18 (m, 1H+1H (1/2.1) ), 9.19 (d, 1H (1/2.1), J = 2.4 Hz), 9.34 (d, 1H (1/2.1), J = 2.4 Hz). [Example 72]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O- (2-methylallyl) oxime (Compound No. A3-49)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 1.78 (s, 3H (1.1 / 2.1)), 1.81 (s, 3H (1 / 2.1)), 4.68 (s, 2H (1.1 / 2.1)), 4.72 ( s, 2H (1 / 2.1)), 4.92-4.97 (m, 2H), 7.18-7.81 (m, 6H + 1H (1.1 / 2.1)), 8.09-8.18 (m, 1H + 1H (1 / 2.1)) , 9.19 (d, 1H (1 / 2.1), J = 2.4 Hz), 9.34 (d, 1H (1 / 2.1), J = 2.4 Hz).
[実施例７３]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-cyanomethyloxime（化合物番号A3－50）
物性：m. p. 114-116 ℃ [Example 73]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-cyanomethyloxime (Compound No. A3-50)
Physical properties: m. P. 114-116 ℃
[実施例７４]
(2,3-Dichlorophenyl)-(6-methoxyquinolin-3-yl)-methanone O-methyloxime（化合物番号A3－55）
物性：m. p. 43-45 ℃ [Example 74]
(2,3-Dichlorophenyl)-(6-methoxyquinolin-3-yl) -methanone O-methyloxime (Compound No. A3-55)
Physical properties: m. P. 43-45 ℃
[実施例７５]
(2,3-Dichlorophenyl)-3-quinolinyl-methanone O-phenyloxime（化合物番号A3－57）
物性：amorphous
1H-NMR (300 MHz, CDCl3) δ 7.05-7.11 (m, 1H), 7.22-7.44 (m, 6H), 7.54-7.83(m, 4H), 7.96 (d, 1H, J = 2.1 Hz), 8.15 (d 1H, J = 8.4 Hz), 9.46 (d, 1H, J = 2.1 Hz). [Example 75]
(2,3-Dichlorophenyl) -3-quinolinyl-methanone O-phenyloxime (Compound No. A3-57)
Physical property: amorphous
1 H-NMR (300 MHz, CDCl 3 ) δ 7.05-7.11 (m, 1H), 7.22-7.44 (m, 6H), 7.54-7.83 (m, 4H), 7.96 (d, 1H, J = 2.1 Hz) , 8.15 (d 1H, J = 8.4 Hz), 9.46 (d, 1H, J = 2.1 Hz).
[実施例７６]
(2,6-Difluorophenyl)-3-quinolinyl-methanone O-methyloxime（化合物番号A3－59）
物性：m. p. 72-74 ℃ [Example 76]
(2,6-Difluorophenyl) -3-quinolinyl-methanone O-methyloxime (Compound No. A3-59)
Physical properties: m. P. 72-74 ℃
（製剤）
　次に、本発明殺菌剤の実施例を若干示すが、添加物及び添加割合は、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, although the Example of this invention disinfectant is shown a few, an additive and an addition ratio should not be 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 Compound of the present invention 40 parts Clay 48 parts Dioctylsulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts or more are uniformly mixed and finely pulverized, and 40% active ingredient wettable powder Get.
製剤実施例２　　　　乳剤
　　本発明化合物　　　　　　　　　　　　　　　　　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 Compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts or more are mixed and dissolved to obtain an emulsion containing 10% active ingredient.
製剤実施例３　　　　粉剤
　　本発明化合物　　　　　　　　　　　　　　　　　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 Powder A compound of the present invention 10 parts Clay 90 parts or more are mixed uniformly and finely pulverized to obtain a powder of 10% active ingredient.
製剤実施例４　　　　粒剤
　　本発明化合物　　　　　　　　　　　　　　　　　　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 Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part or more is pulverized and mixed well, and after adding water and kneading well, granulation drying As a result, granules containing 5% of the active ingredient are obtained.
製剤実施例５　　　　懸濁剤
　　本発明化合物　　　　　　　　　　　　　　　　　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 Suspension 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 or more are mixed and the particle size is 3 microns or less The suspension is wet-pulverized until a suspension of 10% active ingredient is obtained.
製剤実施例６　　　　顆粒水和剤
　　本発明化合物　　　　　　　　　　　　　　　　　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 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 or more uniformly mixed After finely pulverizing, add an appropriate amount of water and knead to make clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.
(試験)
（試験例１）リンゴ黒星病防除試験
　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、下記に示す本発明化合物の乳剤を有効成分１００ｐｐｍの濃度で散布した。室温で自然乾燥した後、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。 (test)
(Test Example 1) Apple black spot disease control test An emulsion of the compound of the present invention shown below was sprayed at a concentration of 100 ppm active ingredient on apple seedlings (variety “Kokumitsu”, 3-4 leaf stage) cultivated in an unglazed pot. After natural drying at room temperature, conidia spores of Venturia inaequalis were inoculated and kept in a room of 20 ° C. and high humidity for 2 weeks, repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
　その結果、下記の化合物は、７５％以上の優れた防除価を示した。
化合物番号（表１～表３の化合物番号に対応）：Ａ２－１、Ａ２－１２、Ａ２－１３、Ａ２－１４、Ａ２－１５、Ａ２－１６、Ａ２－２０、Ａ２－２３、Ａ２－３０、Ａ３－１、Ａ３－２、Ａ３－３、Ａ３－５、Ａ３－６、Ａ３－７、Ａ３－８、Ａ３－９、Ａ３－１０、Ａ３－１２、Ａ３－１３、Ａ３－１９（ｍｉｘ）、Ａ３－１９（ｉｓｏ）、Ａ３－２０、Ａ３－２１、Ａ３－２２、Ａ３－２３、Ａ３－２４、Ａ３－２６、Ａ３－２７、Ａ３－２８、Ａ３－２９、Ａ３－３０、Ａ３－３１、Ａ３－３２、Ａ３－３３、Ａ３－３４、Ａ３－３５、Ａ３－３６、Ａ３－３７（ｍｉｘ）、Ａ３－３７（ｉｓｏ）、Ａ３－４２、Ａ３－４３、Ａ３－４４、Ａ３－４５、Ａ３－４６、Ａ３－４７、Ａ３－４９、Ａ３－５０ As a result, the following compounds showed an excellent control value of 75% or more.
Compound numbers (corresponding to the compound numbers in Tables 1 to 3): A2-1, A2-12, A2-13, A2-14, A2-15, A2-16, A2-20, A2-23, A2-30 A3-1, A3-2, A3-3, A3-5, A3-6, A3-7, A3-8, A3-9, A3-10, A3-12, A3-13, A3-19 (mix ), A3-19 (iso), A3-20, A3-21, A3-22, A3-23, A3-24, A3-26, A3-27, A3-28, A3-29, A3-30, A3 -31, A3-32, A3-33, A3-34, A3-35, A3-36, A3-37 (mix), A3-37 (iso), A3-42, A3-43, A3-44, A3 -45, A3-46, A3-47, A3-49, A3-50
（試験例２）キュウリ灰色かび病防除試験
　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、下記に示す本発明化合物の乳剤を有効成分１００ｐｐｍの濃度で散布した。室温で自然乾燥した後、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、暗所、２０℃、高湿度の室内に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。 (Test Example 2) Cucumber Gray Mold Control Test A cucumber seedling (cultivar “Sagamihanjiro”, cotyledon stage) cultivated in an unglazed pot was sprayed with the following emulsion of the present compound at a concentration of 100 ppm active ingredient. After natural drying at room temperature, a conidial spore suspension of cucumber gray mold fungus (Botrytis cinerea) was inoculated dropwise and kept in a dark place at 20 ° C. in a high humidity room for 4 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
　その結果、下記の化合物は、７５％以上の優れた防除価を示した。
 化合物番号（表１～表３の化合物番号に対応）：Ａ２－３０、Ａ３－１９（ｍｉｘ）、Ａ３－１９（ｉｓｏ）、Ａ３－２０、Ａ３－２１、Ａ３－２２、Ａ３－２６、Ａ３－２８、Ａ３－３２、Ａ３－３３、Ａ３－３４、Ａ３－３５、Ａ３－３７（ｍｉｘ）、Ａ３－３７（ｉｓｏ）、Ａ３－４３、Ａ３－５０、Ａ３－５９ As a result, the following compounds showed an excellent control value of 75% or more.
Compound numbers (corresponding to the compound numbers in Tables 1 to 3): A2-30, A3-19 (mix), A3-19 (iso), A3-20, A3-21, A3-22, A3-26, A3 -28, A3-32, A3-33, A3-34, A3-35, A3-37 (mix), A3-37 (iso), A3-43, A3-50, A3-59
　本発明の含窒素ヘテロ環化合物及び／又はその塩を有効成分とする農園芸用殺菌剤は、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ので、産業上有用である。 The agricultural and horticultural fungicide comprising the nitrogen-containing heterocyclic compound and / or salt thereof of the present invention as an active ingredient has an excellent control effect, does not cause phytotoxicity to plants, and is toxic to human livestock and to the environment. This is industrially useful.

Claims (4)

  1. 式（Ｉ）
    Figure JPOXMLDOC01-appb-C000009
     （式中、Ｘは、置換基を有してもよいＣ１～１２アルキル基、置換基を有してもよいＣ２～１２アルケニル基、置換基を有してもよいＣ２～１２アルキニル基、置換基を有してもよいＣ３～１２シクロアルキル基、置換基を有してもよいＣ４～１２シクロアルケニル基、置換基を有してもよいＣ８～１２シクロアルキニル基、置換基を有してもよいヘテロ環基、置換基を有してもよいＣ１～１２アシル基、置換基を有してもよい（１－イミノ）Ｃ１～１２アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、又はニトロ基を示す。
    　ｍは、０～６のいずれかの整数を示す。ｍが２以上のとき、Ｘは互いに同一でも異なっていてもよい。
    　隣接する原子上に置換されたＸは、一緒になって、置換基を有してもよい５～８員環を形成してもよい。
    　Ｒは、置換基を有してもよいＣ１～１２アルキル基、置換基を有してもよいＣ２～１２アルケニル基、置換基を有してもよいＣ２～１２アルキニル基、置換基を有してもよいＣ３～１２シクロアルキル基、置換基を有してもよいＣ４～１２シクロアルケニル基、置換基を有してもよいＣ８～１２シクロアルキニル基、置換基を有してもよいＣ６～１２アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいＣ１～１２アシル基、又は、置換基を有するスルホニル基を示す。
    　Ｑは、置換基を有してもよいＣ６～１２アリール基、又は置換基を有してもよいヘテロ環基を示す。
    　Ａは、夫々独立して、炭素原子、窒素原子、酸素原子又は硫黄原子を示し、ｎは、１又は２の整数を示す。実線と点線の二重線は単結合又は２重結合を示す。）
    で表される含窒素ヘテロ環化合物又はその塩。     Formula (I)
    Figure JPOXMLDOC01-appb-C000009
     Wherein X is a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, a C2-12 alkynyl group which may have a substituent, a substituted A C3-12 cycloalkyl group which may have a group, a C4-12 cycloalkenyl group which may have a substituent, a C8-12 cycloalkynyl group which may have a substituent, and a substituent. An optionally substituted heterocyclic group, an optionally substituted C1-12 acyl group, an optionally substituted (1-imino) C1-12 alkyl group, an optionally substituted hydroxyl group, a substituted An amino group which may have a group, a mercapto group which may have a substituent, a sulfonyl group having a substituent, a halogeno group, a cyano group or a nitro group.
    m represents an integer of 0 to 6. When m is 2 or more, Xs may be the same or different from each other.
    X substituted on adjacent atoms may be taken together to form a 5- to 8-membered ring which may have a substituent.
    R has a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, a C2-12 alkynyl group which may have a substituent, and a substituent. An optionally substituted C3-12 cycloalkyl group, an optionally substituted C4-12 cycloalkenyl group, an optionally substituted C8-12 cycloalkynyl group, an optionally substituted C6-12 12 represents an aryl group, an optionally substituted heterocyclic group, an optionally substituted C1-12 acyl group, or a substituted sulfonyl group.
    Q represents a C6-12 aryl group which may have a substituent, or a heterocyclic group which may have a substituent.
    A independently represents a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and n represents an integer of 1 or 2. A solid line and a dotted double line indicate a single bond or a double bond. )
    Or a salt thereof.
  2. 式（ＩＩ）
    Figure JPOXMLDOC01-appb-C000010
     （式中、Ｘ、ｍ、Ｒ及びＱは、前記と同様の意味を示す。）で表される請求項１記載の含窒素ヘテロ環化合物又はその塩。     Formula (II)
    Figure JPOXMLDOC01-appb-C000010
     (Wherein, X, m, R and Q have the same meanings as described above).
  3. 式（ＩＩＩ）
    Figure JPOXMLDOC01-appb-C000011
     （式中、Ｘ、ｍ及びＲは、前記と同様の意味を示す。
    　Ｘ’は、夫々独立して、置換基を有してもよいＣ１～１２アルキル基、置換基を有してもよいＣ２～１２アルケニル基、置換基を有してもよいＣ２～１２アルキニル基、置換基を有してもよいＣ３～１２シクロアルキル基、置換基を有してもよいＣ４～１２シクロアルケニル基、置換基を有してもよいＣ８～１２シクロアルキニル基、置換基を有してもよいＣ６～１２アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいＣ１～１２アシル基、置換基を有してもよい（１－イミノ）Ｃ１～１２アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、又はニトロ基を示す。
    　ｓは、０～５のいずれかの整数を示す。ｓが２以上のとき、Ｘ’は互いに同一でも異なっていてもよい。
    　隣接する原子上に置換されたＸ’は、一緒になって、置換基を有してもよい５～８員環を形成してもよい。）
    で表される請求項１記載の含窒素ヘテロ環化合物又はその塩。     Formula (III)
    Figure JPOXMLDOC01-appb-C000011
     (In the formula, X, m and R have the same meaning as described above.
    X ′ is independently a C1-12 alkyl group which may have a substituent, a C2-12 alkenyl group which may have a substituent, or a C2-12 alkynyl group which may have a substituent. A C3-12 cycloalkyl group which may have a substituent, a C4-12 cycloalkenyl group which may have a substituent, a C8-12 cycloalkynyl group which may have a substituent, and a substituent. An optionally substituted C6-12 aryl group, an optionally substituted heterocyclic group, an optionally substituted C1-12 acyl group, an optionally substituted (1-imino) C1 ~ 12 alkyl group, hydroxyl group optionally having substituent, amino group optionally having substituent, mercapto group optionally having substituent, sulfonyl group having substituent, halogeno group, cyano group, Or a nitro group is shown.
    s represents an integer of 0 to 5. When s is 2 or more, X ′ may be the same as or different from each other.
    X ′ substituted on adjacent atoms may be taken together to form a 5- to 8-membered ring which may have a substituent. )
    The nitrogen-containing heterocyclic compound of Claim 1 represented by these, or its salt.
  4. 　請求項１～３のいずれに記載の含窒素へテロ環化合物又はその塩の少なくとも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 of the nitrogen-containing heterocyclic compounds or salts thereof according to any one of claims 1 to 3.
PCT/JP2009/004395 2008-09-08 2009-09-04 Nitrogenated heterocyclic compound and salt thereof, and bactericidal agent for agricultural or horticultural applications WO2010026771A1 (en)

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CN112912374A (en) * 2018-10-20 2021-06-04 拜耳公司 Oxocyclobutylphenoxyquinolines and analogs
US11661422B2 (en) 2020-08-27 2023-05-30 Incyte Corporation Tricyclic urea compounds as JAK2 V617F inhibitors
US11691971B2 (en) 2020-06-19 2023-07-04 Incyte Corporation Naphthyridinone compounds as JAK2 V617F inhibitors
US11753413B2 (en) 2020-06-19 2023-09-12 Incyte Corporation Substituted pyrrolo[2,1-f][1,2,4]triazine compounds as JAK2 V617F inhibitors
US11767323B2 (en) 2020-07-02 2023-09-26 Incyte Corporation Tricyclic pyridone compounds as JAK2 V617F inhibitors
US11780840B2 (en) 2020-07-02 2023-10-10 Incyte Corporation Tricyclic urea compounds as JAK2 V617F inhibitors
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US11919908B2 (en) 2020-12-21 2024-03-05 Incyte Corporation Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors
US11958861B2 (en) 2021-02-25 2024-04-16 Incyte Corporation Spirocyclic lactams as JAK2 V617F inhibitors

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WO2011081174A1 (en) * 2010-01-04 2011-07-07 日本曹達株式会社 Nitrogen-containing heterocyclic compound and agricultural/horticultural germicide
US8772200B2 (en) 2010-01-04 2014-07-08 Nippon Soda Co., Ltd. Nitrogen-containing heterocyclic compound and agricultural fungicide
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WO2018053587A1 (en) * 2016-09-21 2018-03-29 Vectus Biosystems Limited Compositions for the treatment of hypertension and/or fibrosis
CN112912374A (en) * 2018-10-20 2021-06-04 拜耳公司 Oxocyclobutylphenoxyquinolines and analogs
US11691971B2 (en) 2020-06-19 2023-07-04 Incyte Corporation Naphthyridinone compounds as JAK2 V617F inhibitors
US11753413B2 (en) 2020-06-19 2023-09-12 Incyte Corporation Substituted pyrrolo[2,1-f][1,2,4]triazine compounds as JAK2 V617F inhibitors
US11767323B2 (en) 2020-07-02 2023-09-26 Incyte Corporation Tricyclic pyridone compounds as JAK2 V617F inhibitors
US11780840B2 (en) 2020-07-02 2023-10-10 Incyte Corporation Tricyclic urea compounds as JAK2 V617F inhibitors
US11661422B2 (en) 2020-08-27 2023-05-30 Incyte Corporation Tricyclic urea compounds as JAK2 V617F inhibitors
US11919908B2 (en) 2020-12-21 2024-03-05 Incyte Corporation Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors
US11958861B2 (en) 2021-02-25 2024-04-16 Incyte Corporation Spirocyclic lactams as JAK2 V617F inhibitors
US11820747B2 (en) 2021-11-02 2023-11-21 Flare Therapeutics Inc. PPARG inverse agonists and uses thereof

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