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WO2010026771A1 - Composé hétérocyclique azoté et son sel, et agent bactéricide pour des applications en agriculture ou horticulture - Google Patents

Composé hétérocyclique azoté et son sel, et agent bactéricide pour des applications en agriculture ou horticulture 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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English (en)
Japanese (ja)
Inventor
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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Nippon Soda Co Ltd
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Nippon Soda Co Ltd
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Priority to JP2010527708A priority Critical patent/JP5281647B2/ja
Publication of WO2010026771A1 publication Critical patent/WO2010026771A1/fr
Anticipated expiration legal-status Critical
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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.

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Abstract

L'invention concerne un composé hétérocyclique azoté représenté par la formule (I) [dans laquelle X représente un groupe alkyle en C1-12 qui peut avoir un substituant, ou autre, et m représente un entier de 0 à 6, à condition que, lorsque m représente un entier supérieur ou égal à 2, les X puissent être les mêmes ou différents les uns des autres ; R représente un groupe alkyle en C1-12 qui peut avoir un substituant, ou autre ; Q représente un groupe aryle en C6-12 qui peut avoir un substituant, ou autre ; les A représentent indépendamment un atome de carbone ou autre ; n représente un entier de 1 ou 2, et la double ligne formée par une ligne continue et une ligne en tirets représente une liaison simple ou une double liaison], et un sel de celui-ci.
PCT/JP2009/004395 2008-09-08 2009-09-04 Composé hétérocyclique azoté et son sel, et agent bactéricide pour des applications en agriculture ou horticulture Ceased WO2010026771A1 (fr)

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CN112912374A (zh) * 2018-10-20 2021-06-04 拜耳公司 氧杂环丁基苯氧基喹啉及类似物
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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
US11820747B2 (en) 2021-11-02 2023-11-21 Flare Therapeutics Inc. PPARG inverse agonists and uses thereof
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
US12084430B2 (en) 2022-03-17 2024-09-10 Incyte Corporation Tricyclic urea compounds as JAK2 V617F inhibitors

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