WO2022224924A1 - Nitrogen-containing heteroaryl compound, agricultural and horticultural anti-bacterial agent, nematicide, and anti-fungal agent for medical and veterinary uses - Google Patents

Nitrogen-containing heteroaryl compound, agricultural and horticultural anti-bacterial agent, nematicide, and anti-fungal agent for medical and veterinary uses Download PDF

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WO2022224924A1
WO2022224924A1 PCT/JP2022/018006 JP2022018006W WO2022224924A1 WO 2022224924 A1 WO2022224924 A1 WO 2022224924A1 JP 2022018006 W JP2022018006 W JP 2022018006W WO 2022224924 A1 WO2022224924 A1 WO 2022224924A1
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unsubstituted
represented
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French (fr)
Japanese (ja)
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貴昭 寺西
頼人 ▲桑▼原
達弘 川崎
拓真 石原
睦幸 斎賀
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日本曹達株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P5/00—Nematocides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • C—CHEMISTRY; METALLURGY
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
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    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to nitrogen-containing heteroaryl compounds and agricultural and horticultural fungicides. More specifically, the present invention relates to a nitrogen-containing heteroaryl compound that has excellent bactericidal and antibacterial activity, is excellent in safety, and can be industrially advantageously synthesized, and an agricultural and horticultural fungicide containing the same as an active ingredient. Furthermore, it relates to a nematicide containing the above compound as an active ingredient. Furthermore, it relates to medical and veterinary antifungal agents containing the above compounds as active ingredients.
  • This application is based on Japanese Patent Application No. 2021-073123 filed on April 23, 2021, Japanese Patent Application No. 2021-131946 filed on August 13, 2021 and on October 6, 2021 A priority is claimed with respect to the Japanese patent application No. 2021-165098 which was filed, and the content is used here.
  • Patent Literature 1 discloses a compound represented by the formula (A) and the like.
  • An object of the present invention is to provide a nitrogen-containing heteroaryl compound that has excellent bactericidal and antibacterial activity, is excellent in safety, and can be industrially advantageously synthesized, and an agricultural and horticultural fungicide containing this as an active ingredient. be.
  • a further object is to provide a nematicide containing the above compound as an active ingredient.
  • a further object of the present invention is to provide medical and veterinary antifungal agents containing the aforementioned compounds as active ingredients.
  • Y 1 represents an oxygen atom or a sulfur atom
  • X 1 , X 2 and X 4 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2- 6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfin
  • a nematicide containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] or [2] and salts thereof.
  • a medical or veterinary antifungal agent containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] or [2] and salts thereof.
  • the nitrogen-containing heteroaryl compound of the present invention is excellent in bactericidal and antibacterial activity, has a reliable effect, is excellent in safety, and can be industrially advantageously synthesized.
  • the agricultural and horticultural fungicide and nematicide of the present invention have an excellent control effect, do not cause phytotoxicity to plants, and are less toxic to humans, livestock and fish, and have less impact on the environment.
  • the medical and veterinary antifungal agents of the present invention have excellent antibacterial effects and are less toxic to humans, animals, and fish.
  • the nitrogen-containing heteroaryl compound of the present invention is a compound represented by formula (I-1), a compound represented by formula (I-2), or a compound represented by formula (I-3) (hereinafter, compound (I)) or a salt of compound (I).
  • the term "unsubstituted” means only scaffolding groups. When only the name of the base group is used, it means “unsubstituted” unless otherwise specified.
  • the term “substituted” means that one of the hydrogen atoms in the scaffold group is replaced with a group having the same or different structure as that of the scaffold.
  • a “substituent” is another group attached to a scaffold group.
  • the number of substituents may be one, or two or more. Two or more substituents may be the same or different.
  • a “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
  • groups that can be “substituents” include the following groups. Halogeno groups such as fluoro, chloro, bromo and iodo groups; C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group alkyl group; vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group , 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group,
  • C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; 2-cyclopropenyl group, 2-cyclopentenyl group, C3-6 cycloalkenyl group such as 3-cyclohexenyl group; C6-10 aryl group such as phenyl group and naphthyl group; C6-10 aryl C1-6 alkyl groups such as benzyl group and phenethyl group; 3- to 6-membered heterocyclyl group; 3- to 6-membered heterocyclyl C1-6 alkyl group;
  • C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy and t-butoxy
  • C2-6 alkenyloxy groups such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group
  • C2-6 alkynyloxy groups such as an ethynyloxy group and a propargyloxy group
  • C6-10 aryloxy groups such as phenoxy group and naphthoxy group
  • C6-10 aryl C1-6 alkoxy groups such as benzyloxy group and phenethyloxy group
  • carboxy group formyl group; C1-6 alkylcarbonyl groups such as acetyl group and propionyl group; formyloxy group; C1-6 alkylcarbonyloxy groups such as an acetyloxy group and a propionyloxy group; Methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, C1-6 alkoxycarbonyl group such as t-butoxycarbonyl group;
  • C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; C3-6 halocycloalkyl groups such as 3,3-difluorocyclobutyl groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group; C2-6 haloalken
  • amino group amino group
  • C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group and diethylamino group
  • C6-10 arylamino groups such as anilino group and naphthylamino group
  • C6-10 aryl C1-6 alkylamino groups such as benzylamino group and phenethylamino group
  • C1-6 alkylcarbonylamino groups such as acetylamino group, propionylamino group, butyrylamino group, i-propylcarbonylamino group
  • C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group
  • unsubstituted or substituted aminocarbonyl group such as carbamoyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N-phenyl-N-methylaminocarbonyl group
  • imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, (1-imino)-n-propyl group; N-hydroxy-iminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)
  • C1-6 alkylthio groups such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio and t-butylthio; C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group; C2-6 alkenylthio groups such as a vinylthio group and an allylthio group; C2-6 alkynylthio groups such as ethynylthio group and propargylthio group; C1-6 alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as a methyl
  • tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group and t-butyldimethylsilyl group; tri-C6-10 aryl-substituted silyl groups such as triphenylsilyl groups; cyano group; nitro group;
  • C1-6 indicates that the number of carbon atoms in the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms in substituent groups.
  • an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the base group is a butyl group and the substituent is an ethoxy group.
  • the above-mentioned "3- to 6-membered heterocyclyl group” contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur atoms as ring-constituting atoms.
  • the "3- to 6-membered heterocyclyl group” includes a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
  • 3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, A dioxolanyl group, a dioxanyl group and the like can be mentioned.
  • Five-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
  • a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, etc. can be mentioned as a 6-membered heteroaryl group.
  • Examples of the 5-membered partially unsaturated heterocyclyl group include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, and isoxazolinyl groups.
  • Examples of the 6-membered partially unsaturated heterocyclyl group include a dihydropyranyl group. Any hydrogen atom in these "substituents" may be substituted with a group having a different structure.
  • Y 1 represents an oxygen atom or a sulfur atom.
  • Y 1 is preferably an oxygen atom.
  • X 1 , X 2 and X 4 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group , a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or
  • R 1 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ⁇ 6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • R 2 is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo It represents an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • R 3 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ⁇ 6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • Each R 4 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
  • R 3 and R 4 may together form a divalent organic group.
  • Each R 5 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
  • R 6 is a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, It represents a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group and an iodo group.
  • the “C1-6 alkyl group” for X 1 , X 2 and X 4 may be linear or branched.
  • the "C1-6 alkyl group” for X 1 includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
  • the "C2-6 alkenyl group" for X 1 , X 2 and X 4 includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl -2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2- butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • the "C2-6 alkynyl group" for X 1 , X 2 and X 4 includes an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl -2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3- Pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like can be mentioned.
  • the "C1-6 alkoxy group" for X 1 , X 2 and X 4 includes methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
  • Examples of the “C2-6 alkenyloxy group” for X 1 , X 2 and X 4 include vinyloxy, allyloxy, propenyloxy, butenyloxy and the like.
  • Examples of the "C2-6 alkynyloxy group” for X 1 , X 2 and X 4 include an ethynyloxy group and a propargyloxy group.
  • the "C1-6 alkylthio group" for X 1 , X 2 and X 4 includes methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, i-propylthio and the like. can be mentioned.
  • Examples of the "C1-6 alkylsulfinyl group” for X 1 , X 2 and X 4 include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
  • Examples of the “C1-6 alkylsulfonyl group” for X 1 , X 2 and X 4 include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.
  • C1-6 alkyl group “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C2-6 alkenyloxy group” for X 1 , X 2 and X 4
  • Substituents on the "C2-6 alkynyloxy group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” or “C1-6 alkylsulfonyl group” include a fluoro group, a chloro group and a bromo group , a halogeno group such as an iodine group; a hydroxyl group; Alkoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1-6 haloalkoxy group such as trifluoromethoxy group; (ethylideneamino)oxy group, propane-2-ylideneamino)oxy group and the like (C1-6 alkylideneamino
  • Examples of the “C3-6 cycloalkyl group” for X 1 , X 2 and X 4 include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.
  • Examples of the "C3-6 cycloalkyloxy group” for X 1 , X 2 and X 4 include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
  • Examples of the “C6-10 aryl group” for X 1 , X 2 and X 4 include phenyl group, naphthyl group, indanyl group, indenyl group, tetralinyl group and the like.
  • Examples of the “C6-10 aryloxy group” for X 1 , X 2 and X 4 include a phenoxy group and a naphthoxy group.
  • Examples of the “C6-10 arylthio group” for X 1 , X 2 and X 4 include a phenylthio group and a naphthylthio group.
  • Examples of the “C6-10 arylsulfinyl group” for X 1 , X 2 and X 4 include a phenylsulfinyl group and a naphthylsulfinyl group.
  • Examples of the “C6-10 arylsulfonyl group” for X 1 , X 2 and X 4 include a phenylsulfonyl group and a naphthylsulfonyl group.
  • the “5- to 6-membered heterocyclyl group” for X 1 , X 2 and X 4 means that 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom are added to the ring. It is a group containing as a constituent atom. When there are two or more heteroatoms, they may be the same or different.
  • Examples of the "5- to 6-membered heterocyclyl group” include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
  • Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
  • Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
  • 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
  • 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.
  • the “5- to 6-membered heterocyclyloxy group” for X 1 , X 2 and X 4 has a structure in which a 5- to 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.
  • R 1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group indicate.
  • the "C1-6 alkyl group” for R 1 includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
  • Examples of the “C2-6 alkenyl group” for R 1 include a vinyl group and a 1-propenyl group.
  • Examples of the “C2-6 alkynyl group” for R 1 include an ethynyl group and a 1-propynyl group.
  • substituents on the "C1-6 alkyl group", “C2-6 alkenyl group", or “C2-6 alkynyl group” in R 1 include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, t-butoxy; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phenyl group,
  • 6-membered ring heteroaryl group C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents 6
  • a membered ring heteroaryl group; or a cyano group is preferred.
  • Examples of the “C3-6 cycloalkyl group” for R 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the “C6-10 aryl group” for R 1 include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.
  • the “5- to 6-membered heterocyclyl group” for R 1 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different.
  • Examples of the "5- to 6-membered heterocyclyl group” include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
  • Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
  • Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
  • 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
  • 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro A 6-membered partially unsaturated heterocyclyl group such as a pyranyl group can be mentioned.
  • Substituents on the "C3-6 cycloalkyl group", “C6-10 aryl group”, or “5- to 6-membered heterocyclyl group” for R 1 include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • R 1 -CO- examples include formyl, acetyl, propionyl, butyryl, i-propylcarbonyl and the like.
  • R 2 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group , a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group show.
  • substituents for R 2 are the same as those exemplified for R 1 .
  • R 2 —O—CO— examples include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group and the like.
  • R 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl
  • R 4 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Specific examples of substituents for R 3 or R 4 are the same as those exemplified for R 1 .
  • R 3 and R 4 may together form a divalent organic group.
  • Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
  • Examples of the "C2-5 alkylene group” include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
  • Examples of the "C1-3 alkyleneoxy C1-3 alkylene group” include a dimethyleneoxydimethylene group and the like.
  • substituents on the "C2-5 alkylene group” or "C1-3 alkyleneoxy C1-3 alkylene group” include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
  • halogeno groups such as fluoro, chloro, bromo, and iodo groups
  • methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group
  • R 3 R 4 N— examples include amino group, methylamino group, dimethylamino group, i-propylamino group and the like.
  • R 3 R 4 N—CO— for X 1 , X 2 and X 4 , R 3 and R 4 are the same as those in the above “group represented by R 3 R 4 N—” have similar meanings.
  • Specific examples of the “group represented by R 3 R 4 N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, an N-(i-propyl )—N-methylaminocarbonyl group and the like.
  • R 1 has the same meaning as the above "group represented by R 1 -CO-".
  • Specific examples of the "group represented by R 1 -CO-O-" include an acetyloxy group and an i-propylcarbonyloxy group.
  • R 1 has the same meaning as in the above "group represented by R 1 -CO-".
  • R 5 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Specific examples of substituents for R 5 are the same as those exemplified for R 1 . Specific examples of the "group represented by R 1 -CO-NR 5 -" include an acetylamino group and an i-propylcarbonylamino group.
  • R 2 is the same as the above “group represented by R 2 —O—CO—” indicate meaning.
  • Specific examples of the “group represented by R 2 —O—CO—O—” include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.
  • R 2 is the same as in the above "group represented by R 2 -O-CO-” indicates the meaning of R 5 has the same meaning as in the above “group represented by R 1 —CO—NR 5 —”.
  • Specific examples of the “group represented by R 2 —O—CO—NR 5 —” include a methoxycarbonylamino group.
  • R 3 R 4 N—CO—O— for X 1 , X 2 and X 4 , R 3 and R 4 are the above “group represented by R 3 R 4 N—” have similar meanings.
  • Specific examples of the “group represented by R 3 R 4 N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.
  • R 3 R 4 N—CO—NR 5 — for X 1 , X 2 and X 4 , R 3 and R 4 are the above “group represented by R 3 R 4 N—” have similar meanings to those in R 5 has the same meaning as in the above “group represented by R 1 —CO—NR 5 —”.
  • Specific examples of the “group represented by R 3 R 4 N—CO—NR 5 —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.
  • R 2 has the same meaning as in the above "group represented by R 2 -O-CO-”. indicates R 5 has the same meaning as in the above “group represented by R 1 —CO—NR 5 —”.
  • Specific examples of the “group represented by R 2 SO 2 —NR 5 —” include a methanesulfonylamino group and the like.
  • R 3 R 4 N—SO 2 — for X 1 , X 2 and X 4 , R 3 and R 4 are those in the above “group represented by R 3 R 4 N—” has the same meaning as Specific examples of the “group represented by R 3 R 4 N—SO 2 —” include an N,N-dimethylaminosulfonyl group.
  • R1 has the same meaning as in the above "group represented by R1 - CO- ".
  • R 6 is a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, It represents a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • substituted or unsubstituted C1-6 alkyl group or “substituted or unsubstituted 5- to 6-membered heterocyclyl group” for R 6 are the same as those exemplified for R 1 .
  • halogeno group for R 6 include a fluoro group, a chloro group, a bromo group and an iodo group.
  • mono C1-6 alkylamino group of the “substituted or unsubstituted mono C1-6 alkylamino group” for R 6 include a methylamino group, an ethylamino group and an i-propylamino group.
  • Examples of the "di-C1-6 alkylamino group" of the "substituted or unsubstituted di-C1-6 alkylamino group” for R 6 include a dimethylamino group, a diethylamino group, an N-methyl-Ni-propylamino group, and the like. can be mentioned.
  • the "C1-6 alkoxy group" of the "substituted or unsubstituted C1-6 alkoxy group” for R 6 includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, n- A hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group and the like can be mentioned.
  • the "C1-6 alkylthio group" of the "substituted or unsubstituted C1-6 alkylthio group” for R 6 includes methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio groups, i-propylthio groups, and the like.
  • Substituents on the "C1-6 alkoxy group”, “mono-C1-6 alkylamino group”, “di - C1-6 alkylamino group” or “C1-6 alkylthio group” for R 6 include " The same substituents as exemplified as substituents on "C1-6 alkyl group” can be mentioned.
  • [Q] Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.
  • C6-10 aryl group examples include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group, and the like.
  • the “5- to 10-membered heterocyclyl group” for Q is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur atoms as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic. Examples of the "5- to 10-membered heterocyclyl group” include a 5- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .
  • Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
  • Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
  • 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc.
  • 10-membered heteroaryl group examples include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl group; 9-membered partially unsaturated ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;
  • substituents on the "C6-10 aryl group” or “5- to 10-membered heterocyclyl group” in Q include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, C1-6 alkyl groups such as n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; vinyl group, etc.
  • halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group
  • a methyl group, an ethyl group, C1-6 alkyl groups such as n-propyl group, i-propyl group, n-butyl group, s-butyl group,
  • R Q1 may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.); A group represented by R Q1 R Q1 N—CO— (in the formula, R Q1 may be the same or different.
  • R Q1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a A methyleneoxydimethylene group may be formed.); a group represented by R Q1 -CO-O-; a group represented by R Q1 -CO-NR Q3 - (wherein R Q3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to
  • R Q1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.); A pentafluorosulfanyl group, a trimethylsilylethynyl group, a nitro group, or a cyano group are preferred. Furthermore, an oxo group is also preferred as a substituent on the "5- to 10-membered heterocyclyl group".
  • X 3 is a hydrogen atom, a halogeno group, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R A group represented by 1 -CO-, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4- to 6-membered heterocyclyl group.
  • Examples of the “linear C1-6 alkyl group” for X 3 include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group.
  • the "linear C2-6 alkenyl group” for X 3 includes a vinyl group, 1-propenyl group, 2-propenyl 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 and 5-hexenyl group can be mentioned.
  • the "straight-chain C2-6 alkynyl group" for X 3 includes an ethynyl group, 1-propynyl group, 2-propynyl 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 and the like can be mentioned.
  • Examples of the “4-membered heterocyclyl group” for X 3 include an azetidinyl group and an oxetanyl group. Specific examples of other substituents for X 3 are the same as those exemplified for X 1 , X 2 and X 4 .
  • preferred X 3 is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted C6-10 aryl group. can.
  • substituents on the aryl group or substituents on the 4- to 6-membered heterocyclyl group include one or more substituents selected from the following group of substituents (hereinafter, this substituent is sometimes represented by the symbol "G"). Moreover, when there are two or more substituents (G), two of them may combine to form a divalent organic group. Substituent groups are shown below.
  • halogeno group substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1 ⁇ 6 alkylsulfonyl group, substituted or unsubstituted C3 ⁇ 6 cycloalkyl group, substituted or unsubstituted C3 ⁇ 6 cycloalkyloxy group, substituted or unsubstituted C6 ⁇ 10 aryl group, substituted or unsubstit
  • each R a is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 10-membered heterocyclyl group.
  • R b each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo It represents an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • Each R c is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ⁇ 6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • R d each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group, R c and R d may together form a divalent organic group.
  • Each R e independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group.
  • R f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
  • Each R g independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
  • Each R h independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group.
  • Each R i independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group, wherein R h and R i together form a divalent An organic group may be formed.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
  • the "C1-6 alkyl group” for G may be linear or branched.
  • the "C1-6 alkyl group” in G includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s- Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
  • the "C2-6 alkenyl group” in G includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group , 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • the "C2-6 alkynyl group" in G includes an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group , 1,1-dimethyl-2-butynyl group, and the like.
  • the "C1-6 alkoxy group” for G includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, Examples include s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
  • Examples of the "C2-6 alkenyloxy group” for G include a vinyloxy group, an allyloxy group, a propenyloxy group and a butenyloxy group.
  • Examples of the "C2-6 alkynyloxy group” for G include an ethynyloxy group and a propargyloxy group.
  • Examples of the "C1-6 alkylthio group” for G include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group and an i-propylthio group.
  • Examples of the "C1-6 alkylsulfinyl group” for G include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
  • Examples of the "C1-6 alkylsulfonyl group” for G include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.
  • C1-6 alkyl group “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C2-6 alkenyloxy group”, “C2-6 alkynyloxy group” in G ”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” or “C1-6 alkylsulfonyl group” include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group.
  • hydroxyl group methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C1-6 alkylthio groups such as methylthio group and ethylthio group; C1- such as methylsulfinyl group and ethylsulfinyl group C1-6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; C6 such as phenyl group and naphthy
  • Examples of the "C3-6 cycloalkyl group” for G include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the "C3-6 cycloalkyloxy group” for G include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
  • Examples of the "C6-10 aryl group” for G include a phenyl group and a naphthyl group.
  • Examples of the “C6-10 aryloxy group” for G include a phenoxy group and a naphthoxy group.
  • Examples of the "C6-10 arylthio group” for G include a phenylthio group and a naphthylthio group.
  • Examples of the “C6-10 arylsulfinyl group” for G include a phenylsulfinyl group and a naphthylsulfinyl group.
  • Examples of the “C6-10 arylsulfonyl group” for G include a phenylsulfonyl group and a naphthylsulfonyl group.
  • the "3- to 10-membered heterocyclyl group” for G is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic. Examples of the "3- to 10-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .
  • 3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, A dioxolanyl group, a dioxanyl group and the like can be mentioned.
  • Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
  • 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc.
  • 10-membered heteroaryl group examples include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl group; 9-membered partially unsaturated ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;
  • the "3- to 10-membered heterocyclyloxy group" in G has a structure in which a 3- to 10-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.
  • C3-6 cycloalkyl group include a fluoro group, a chloro group, halogeno groups such as bromo group and iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group , C1-6 alkyl groups such as n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethy
  • R G1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.); A group represented by R G1 R G1 N—CO— (R G1 in the formula may be the same or different.
  • R G1 together may be a trimethylene group, tetramethylene group, pentamethylene group, or A methyleneoxydimethylene group may be formed.); a group represented by R G1 -CO-O-; a group represented by R G1 -CO-NR G3 - (wherein R G3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered heteroary
  • RG1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.); A pentafluorosulfanyl group, a nitro group, or a cyano group are preferred. Furthermore, as a substituent on the "C3-6 cycloalkyl group”, “C3-6 cycloalkyloxy group”, “3- to 10-membered heterocyclyl group”, or “3- to 10-membered heterocyclyloxy group” , oxo groups are also preferred.
  • R a is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted It represents a C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 10-membered heterocyclyl group.
  • the "C1-6 alkyl group” for R a includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
  • Examples of the “C2-6 alkenyl group” for R a include a vinyl group and a 1-propenyl group.
  • Examples of the “C2-6 alkynyl group” for R a include an ethynyl group and a 1-propynyl group.
  • substituents on the "C1-6 alkyl group", “C2-6 alkenyl group", or “C2-6 alkynyl group” in R a include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C1-6 alkylthio groups such as methylthio group and ethylthio group; C1-6 groups such as methylsulfinyl group
  • Examples of the “C3-6 cycloalkyl group” for R a include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the “C6-10 aryl group” for R a include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.
  • the “3- to 10-membered heterocyclyl group” for R a is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic. Examples of the "3- to 10-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .
  • 3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, Dioxolanyl group, dioxanyl group and the like can be mentioned.
  • Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
  • 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc.
  • 10-membered heteroaryl group examples include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl group; 9-membered partially unsaturated ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;
  • Substituents on the "C3-6 cycloalkyl group", “C6-10 aryl group”, or “3- to 10-membered heterocyclyl group” for R a include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • R q1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.);
  • a group represented by R q1 R q1 N—CO— (R q1 in the formula may be the same or different.
  • R q1 may be a trimethylene group, a tetramethylene group, a A methyleneoxydimethylene group may be formed.); a group represented by R q1 —CO—O—; a group represented by R q1 —CO—NR q3 — (wherein R q3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered
  • R q1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.); A pentafluorosulfanyl group, a nitro group, or a cyano group are preferred. Furthermore, an oxo group is also preferred as a substituent on the "C3-6 cycloalkyl group” or the "3- to 10-membered heterocyclyl group".
  • R a -CO- examples include a formyl group, an acetyl group, an i-propylcarbonyl group and the like.
  • R b is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ⁇ 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • R b is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ⁇ 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • R b -O-CO- examples include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group and a t-butoxycarbonyl group. and the like.
  • R c is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted A C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and R d is , a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group.
  • R c or R d substituents for R c or R d are the same as those exemplified for R a .
  • the "C1-6 alkoxy group" in R d includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, and an i-butoxy group. , s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
  • substituents on the "C1-6 alkoxy group" in R d include halogeno groups such as fluoro, chloro, bromo and iodo groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group , n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, etc.
  • halogeno groups such as fluoro, chloro, bromo and iodo groups
  • hydroxyl group methoxy group, ethoxy group, n-propoxy group, i-propoxy group , n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichloro
  • R c and R d may together form a divalent organic group.
  • divalent organic groups that can be formed include a substituted or unsubstituted C2-5 alkylene group, a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group, a substituted or unsubstituted C1-3 alkylenethio C1-3 Examples include an alkylene group, or a substituted or unsubstituted C1-3 alkyleneimino C1-3 alkylene group. Additionally, mention may be made of silicon-containing divalent hydrocarbon groups such as -CH 2 CH 2 -Si(CH 3 ) 2 -CH 2 CH 2 -.
  • Examples of the "C2-5 alkylene group” include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
  • Examples of the “C1-3 alkyleneoxy C1-3 alkylene group” include a dimethyleneoxydimethylene group and the like.
  • Examples of the “C1-3 alkylenethio C1-3 alkylene group” include a dimethylenethiodimethylene group and the like.
  • Examples of the “C1-3 alkyleneimino C1-3 alkylene group” include a dimethyleneiminodimethylene group and the like.
  • the imino group of "C1-3 alkylenealkyleneimino C1-3 alkylene group” means -NH-.
  • Substituents on "C2-5 alkylene group", “C1-3 alkyleneoxy C1-3 alkylene group”, “C1-3 alkylenethio C1-3 alkylene group” and “C1-3 alkyleneimino C1-3 alkylene group” examples include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodine group; C1-6 alkyl group such as t-butyl group; methylidene group; or C1 such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group ⁇ 6 haloalkyl groups are preferred.
  • R c R d N— examples include amino group, methylamino group, dimethylamino group, i-propylamino group and the like.
  • R c and R d have the same meanings as those in the above “group represented by R c R d N—”.
  • Specific examples of the “group represented by R c R d N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, an N-(i-propyl )—N-methylaminocarbonyl group and the like.
  • R c and R d have the same meanings as those in the above “group represented by R c R d N—” show.
  • Specific examples of the “group represented by R c R d N—NR d —CO—” include a 2,2-dimethylhydrazine-1-carbonyl group.
  • R b SO 2 —NR d —CO— for G, R b has the same meaning as in the above “group represented by R b —O—CO—”; d has the same meaning as in the above “group represented by R c R d N—”.
  • R b SO 2 -NR d -CO- examples include a (methylsulfonyl)carbamoyl group, a (cyclopropylsulfonyl)carbamoyl group, and a ((1-methylcyclopropyl)sulfonyl)carbamoyl group. etc. can be mentioned.
  • R a has the same meaning as in the above "group represented by R a -CO-".
  • Specific examples of the "group represented by R a -CO-O-" include an acetyloxy group.
  • R a has the same meaning as in the above "group represented by R a -CO-".
  • R e represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group. Specific examples of the substituent for R e are the same as those exemplified for R a .
  • R a -CO-NR e - examples include an acetylamino group, a propionylamino group, a butyrylamino group, an i-propylcarbonylamino group and the like.
  • R a has the same meaning as in the above "group represented by R a -CO-”.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Specific examples of the “group represented by R a —CO—CO—NR e —” include an oxopropanamide group.
  • R a has the same meaning as in the above "group represented by R a -CO-”.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Specific examples of the “group represented by R a —CO—NR e —NR e —” include an acetylhydrazinyl group and an i-propylcarbonylhydrazinyl group.
  • R a has the same meaning as in the above "group represented by R a -CO-”.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Specific examples of the "group represented by R a -CO-NR e -NR e -CO-” include 2-acetylhydrazine-1-carbonyl group.
  • R b has the same meaning as in the above “group represented by R b —O—CO—”.
  • Specific examples of the “group represented by R b —O—CO—O—” include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.
  • R b has the same meaning as in the above “group represented by R b —O—CO—”.
  • R e has the same meaning as in the above “group represented by R b —CO—NR e —”.
  • Specific examples of the “group represented by R b —O—CO—NR e —” include a methoxycarbonylamino group.
  • R c and R d have the same meanings as those in the above “group represented by R c R d N—” .
  • Specific examples of the “group represented by R c R d N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.
  • R c and R d have the same meanings as those in the above “group represented by R c R d N—” show.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Specific examples of the “group represented by R c R d N—CO—NR e —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.
  • R c and R d are the same as those in the above “group represented by R c R d N—” indicate meaning.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Specific examples of the "group represented by R c R d N-CO-CO-NR e -" include 2-(methylamino)-2-oxoacetamide group, 2-(t-butylamino)-2- An oxoacetamide group and the like can be mentioned.
  • R a has the same meaning as in the above "group represented by R a -CO-”.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Specific examples of the "group represented by R a -CS-NR e -" include an ethanethioamide group, a propanethioamide group, a 2-methylpropanethioamide group and the like.
  • Rc and Rd have the same meanings as those in the above "group represented by RcRdN- " . show.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Specific examples of the “group represented by R c R d N—CS—NR e —” include a 3,3-dimethylthioureido group.
  • R b SO 2 —NR e — for G, R b has the same meaning as in the above “group represented by R b —O—CO—”.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Specific examples of the “group represented by R b SO 2 —NR e —” include a methanesulfonylamino group.
  • R c and R d have the same meanings as those in the above “group represented by R c R d N—”.
  • Specific examples of the “group represented by R c R d N—SO 2 —” include an N,N-dimethylaminosulfonyl group.
  • R a has the same meaning as in the above "group represented by R a -CO-”.
  • R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
  • Each R g independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group. Specific examples of the substituent for Rg are the same as those exemplified for Ra .
  • R c and R d are the same as those in the above "group represented by R c R d N-" indicate meaning.
  • each R h is independently a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted represents a C6-10 aryl group, and each R i independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group;
  • substituents for R h or R i are the same as those exemplified for R a .
  • R h and R i may together form a divalent organic group.
  • Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
  • Examples of the "C2-5 alkylene group” include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
  • Examples of the "C1-3 alkyleneoxy C1-3 alkylene group” include a dimethyleneoxydimethylene group and the like.
  • substituents on the "C2-5 alkylene group” or "C1-3 alkyleneoxy C1-3 alkylene group” include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
  • halogeno groups such as fluoro, chloro, bromo, and iodo groups
  • methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group
  • Specific examples of the “group represented by R h R j C ⁇ N—O—” include (propan-2-ylideneamino)oxy group and the like.
  • the divalent organic groups that can be formed by two of them together include a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxy C1-4 An alkylene group, a substituted or unsubstituted oxy C2-3 alkyleneoxy group, or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group can be mentioned.
  • Examples of the "C1-5 alkylene group” include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
  • Examples of the "oxy C1-4 alkylene group” include an oxymethylene group and an oxydimethylene group.
  • Examples of the "oxy C2-3 alkyleneoxy group” include an oxydimethylenoxy group.
  • Examples of the “C1-3 alkyleneoxy C1-3 alkylene group” include a dimethyleneoxydimethylene group and the like.
  • Substituents on the "C1-5 alkylene group", “oxy-C1-4 alkylene group”, “oxy-C2-3 alkyleneoxy group” and “C1-3 alkyleneoxy C1-3 alkylene group” include a fluoro group, chloro Halogeno groups such as group, bromo group and iodo group; C1 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group and t-butyl group ⁇ 6 alkyl group; or C1 ⁇ 6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro
  • preferred G is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 3-10 a membered heterocyclyl group, a group represented by R b --O--CO--, a group represented by R c R d N--, a group represented by R c R d N -- CO---, and R a --CO--- A group represented by O—, a group represented by R a —CO—NR e
  • X 3 is a group represented by R N1 O—, a group represented by R N1 —CO—O—, a group represented by R N1 —O—CO—O—, R N1 R N1 N— a group represented by CO--O--, a group represented by R N1 --CS--O--, a group represented by R N1 R N1 N--CS--O--, a group represented by R N1 R N2 N--- , a group represented by R N1 -CO-NR N2 -, a group represented by R N1 -CO-CO-NR N2 -, a group represented by R N1 -O-CO-NR N2 -, R N1 R A group represented by N1 N—CO—NR N2 —, a group represented by R N1 R N1 N—CO—CO—NR N2 —, a group represented by R N1 —CS—NR N
  • R N1 and R N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R N1 and R N1 , or R N1 and R N2 may together form a divalent organic group.
  • Examples of the "linear C1-6 alkyl group” for R N1 and R N2 include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group.
  • the "linear C2-6 alkenyl group” for R N1 and R N2 includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl and 5-hexenyl groups.
  • the "linear C2-6 alkynyl group" for R N1 and R N2 includes an ethynyl group, 1-propynyl group, 2-propynyl 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 and the like.
  • Examples of the "4-membered heterocyclyl group" for R N1 and R N2 include an azetidinyl group and an oxetanyl group. Specific examples of other substituents for R N1 and R N2 are the same as those exemplified for X 1 .
  • [B] B is a single bond, an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR N3 -, where R N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, formyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group.
  • the “C1-6 alkyl group” in R N3 may be linear or branched.
  • the "C1-6 alkyl group” in R N3 includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
  • Examples of the “C1-6 alkylcarbonyl group” for R N3 include an acetyl group, a propionyl group, a butyryl group, an i-propylcarbonyl group and the like.
  • the substituents on the "C1-6 alkyl group” and "C1-6 alkylcarbonyl" in R N3 include a fluoro group, a chloro group, a bromo group, a halogeno group such as an iodo group; a hydroxyl group; a methoxy group, an ethoxy group, C1-6 alkoxy groups such as n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy group, 2,3- C1-6 haloalkoxy groups such as dichlorobutoxy group and trifluoromethoxy group; (C1-6 alkylideneamino)oxy groups such as (ethylideneamino)oxy group and propane-2-ylideneamino)oxy group; cyclopropyl group and cyclobutyl group , cyclopentyl group, C3-6 cycloalky
  • ring heteroaryl group a 5-membered ring substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group heteroaryl group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered heteroaryl group such as triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or A 6-membered heteroaryl group substituted with one or more substituents selected from C1-6 haloalkoxy groups; or a cyano group is preferred.
  • A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group .
  • Examples of the "C1-6 alkylene group” for A include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
  • Examples of the "C2-6 alkynylene group” for A include an ethynylene group (-C ⁇ C-), a propynylene group (-CH 2 -C ⁇ C-, -C ⁇ C-CH 2 -), and the like.
  • Examples of the "C3-6 cycloalkylene group” for A include 1,2-cyclopropylene group, 1,2-cyclobutanediyl group, 1,3-cyclobutanediyl group and the like.
  • A is preferably a substituted or unsubstituted C1-6 alkylene group or a substituted or unsubstituted C2-6 alkenylene group. More preferred examples of A include a substituted or unsubstituted C2 alkylene group (dimethylene group) and a substituted or unsubstituted C2 alkenylene group (vinylene group). Examples of substituents on the C1-6 alkylene group or C2-6 alkenylene group include one or more substituents selected from the following group of substituents (hereinafter, this substituent is denoted by the symbol "Ga" can be expressed as ).
  • substituents when there are two or more substituents (Ga), two of them may combine to form a divalent organic group.
  • Substituent groups are shown below. halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, mercapto group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted Or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubsti
  • each R a1 is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group
  • R b1 each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubsti
  • R e1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
  • R f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group
  • R g1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, substituted or an unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group
  • R h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, wherein R g1 and R h1 may together form
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, an iodine group, and the like.
  • the "C1-6 alkyl group” in Ga may be linear or branched.
  • the "C1-6 alkyl group” in Ga includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s- Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
  • the "C2-6 alkenyl group” in Ga includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group , 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
  • the "C2-6 alkynyl group" in Ga includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group , 1,1-dimethyl-2-butynyl group, and the like.
  • the "C1-6 alkoxy group” for Ga includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, Examples include s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
  • Examples of the "C2-6 alkenyloxy group” for Ga include a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group.
  • Examples of the "C2-6 alkynyloxy group” for Ga include an ethynyloxy group and a propargyloxy group.
  • Examples of the "C1-6 alkylthio group” for Ga include methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, i-propylthio and the like.
  • Examples of the "C1-6 alkylsulfinyl group” in Ga include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
  • Examples of the "C1-6 alkylsulfonyl group” for Ga include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.
  • C1-6 alkyl group include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group.
  • hydroxyl group methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phenyl group, C6-10 aryl group such as naphthyl group; C1-6 alkyl group such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group , a C1-6 alkoxy group, a halogeno group, a C1-6 halo
  • Examples of the "C3-6 cycloalkyl group” for Ga include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
  • Examples of the "C3-6 cycloalkyloxy group” for Ga include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
  • Examples of the "C6-10 aryl group” for Ga include a phenyl group, naphthyl group, indenyl group, indanyl group, tetralinyl group and the like.
  • Examples of the "C6-10 aryloxy group” in Ga include a phenoxy group and a naphthoxy group.
  • Examples of the "C6-10 arylthio group” in Ga include a phenylthio group and a naphthylthio group.
  • Examples of the “C6-10 arylsulfinyl group” for Ga include a phenylsulfinyl group and a naphthylsulfinyl group.
  • Examples of the “C6-10 arylsulfonyl group” for Ga include a phenylsulfonyl group and a naphthylsulfonyl group.
  • the "3- to 6-membered heterocyclyl group” for Ga is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different.
  • the "3- to 6-membered heterocyclyl group” includes a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
  • 3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, Dioxolanyl group, dioxanyl group and the like can be mentioned.
  • Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
  • Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.
  • the "3- to 6-membered heterocyclyloxy group" in Ga has a structure in which a 3- to 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.
  • C3-6 cycloalkyl group include a fluoro group, a chloro group, halogeno groups such as bromo group and iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group , C1-6 alkyl groups such as n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group
  • R a1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted It represents a C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • the "C1-6 alkyl group" for R a1 includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
  • Examples of the “C2-6 alkenyl group” for R a1 include a vinyl group and a 1-propenyl group.
  • Examples of the “C2-6 alkynyl group” for R a1 include an ethynyl group and a 1-propynyl group.
  • substituents on the "C1-6 alkyl group", “C2-6 alkenyl group", or “C2-6 alkynyl group” in R a1 include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, t-butoxy; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phen
  • Examples of the “C3-6 cycloalkyl group” for R a1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the “C6-10 aryl group” for R a1 include a phenyl group and a naphthyl group.
  • the “5- to 6-membered heterocyclyl group” for R a1 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different.
  • Examples of the "5- to 6-membered heterocyclyl group” include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
  • Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
  • Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups.
  • 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
  • 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.
  • substituents on the "C3-6 cycloalkyl group", “C6-10 aryl group”, or “5- to 6-membered heterocyclyl group” for R a1 include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • R a1 -CO- examples include a formyl group and an acetyl group.
  • R b1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ⁇ 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
  • Specific examples of the substituent for R b1 are the same as those exemplified for R a1 .
  • R b1 -O-CO- examples include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group and the like.
  • R c1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted A C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and R d1 is , a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
  • R c1 or R d1 are the same as those exemplified for R a1 .
  • R c1 and R d1 may together form a divalent organic group.
  • Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
  • Examples of the "C2-5 alkylene group” include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
  • Examples of the "C1-3 alkyleneoxy C1-3 alkylene group” include a dimethyleneoxydimethylene group and the like.
  • substituents on the "C2-5 alkylene group” or "C1-3 alkyleneoxy C1-3 alkylene group” include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
  • halogeno groups such as fluoro, chloro, bromo, and iodo groups
  • methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group
  • R c1 R d1 N- examples include an amino group, a methylamino group and a dimethylamino group.
  • R c1 and R d1 have the same meanings as those in the above “group represented by R c1 R d1 N—”.
  • Specific examples of the “group represented by R c1 R d1 N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, and an N-(i-propyl )—N-methylaminocarbonyl group and the like.
  • R a1 has the same meaning as in the above "group represented by R a1 -CO-".
  • Specific examples of the "group represented by R a1 -CO-O-" include an acetyloxy group.
  • R a1 has the same meaning as in the above "group represented by R a1 -CO-".
  • R e1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
  • Specific examples of the substituent for R e1 are the same as those exemplified for R a1 .
  • Specific examples of the "group represented by R a1 -CO-NR e1 -" include an acetylamino group.
  • R b1 has the same meaning as in the above “group represented by R b1 —O—CO—”.
  • Specific examples of the "group represented by R b1 -O-CO-O-" include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.
  • R b1 has the same meaning as in the above “group represented by R b1 —O—CO—”.
  • R e1 has the same meaning as in the above “group represented by R b1 —CO—NR e1 —”.
  • Specific examples of the “group represented by R b1 —O—CO—NR e1 —” include a methoxycarbonylamino group.
  • R c1 and R d1 have the same meanings as those in the above “group represented by R c1 R d1 N—” .
  • Specific examples of the “group represented by R c1 R d1 N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.
  • R c1 and R d1 have the same meanings as those in the above "group represented by R c1 R d1 N-”. show.
  • R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
  • Specific examples of the “group represented by R c1 R d1 N—CO—NR e1 —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.
  • R b1 SO 2 —NR e1 — has the same meaning as in the above “group represented by R b1 —O—CO—”.
  • R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
  • Specific examples of the “group represented by R b1 SO 2 —NR e1 —” include a methanesulfonylamino group and the like.
  • R c1 and R d1 have the same meanings as those in the above “group represented by R c1 R d1 N—”.
  • Specific examples of the “group represented by R c1 R d1 N—SO 2 —” include an N,N-dimethylaminosulfonyl group.
  • R g1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted represents a substituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, R h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • R g1 or R h1 are the same as those exemplified for R a1 .
  • R g1 and R h1 may together form a divalent organic group.
  • Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
  • Examples of the "C2-5 alkylene group” include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
  • Examples of the "C1-3 alkyleneoxy C1-3 alkylene group” include a dimethyleneoxydimethylene group and the like.
  • Substituents on the "C2-5 alkylene group” or "C1-3 alkyleneoxy C1-3 alkylene group” include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl group, ethyl group, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
  • R a1 has the same meaning as in the above "group represented by R a1 -CO-".
  • R a1 ON for Ga
  • R a1 has the same meaning as in the above "group represented by R a1 -CO-”.
  • R c1 and R d1 have the same meanings as those in the above "group represented by R c1 R d1 N-”. show.
  • R a1 has the same meaning as in the above "group represented by R a1 -CO-”.
  • R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
  • R b1 has the same meaning as in the above “group represented by R b1 —O—CO—” indicate.
  • R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
  • R b1 SO 2 —NR e1 —N ” in Ga
  • R b1 has the same meaning as in the above “group represented by R b1 —O—CO—” .
  • R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
  • the divalent organic group that can be formed by two of them together includes a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxy C1-4
  • An alkylene group, a substituted or unsubstituted oxy C2-3 alkyleneoxy group, or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group can be mentioned.
  • Examples of the "C1-5 alkylene group” include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
  • Examples of the "oxy C1-4 alkylene group” include an oxymethylene group and an oxydimethylene group.
  • Examples of the "oxy C2-3 alkyleneoxy group” include an oxydimethylenoxy group.
  • Examples of the “C1-3 alkyleneoxy C1-3 alkylene group” include a dimethyleneoxydimethylene group and the like.
  • Substituents on the "C1-5 alkylene group", “oxy-C1-4 alkylene group”, “oxy-C2-3 alkyleneoxy group” and “C1-3 alkyleneoxy C1-3 alkylene group” include a fluoro group, chloro Halogeno groups such as group, bromo group and iodo group; C1 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group and t-butyl group ⁇ 6 alkyl group; or C1 ⁇ 6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro
  • a preferred substituted or unsubstituted 5- to 6-membered heterocyclyloxy group is a tetrahydro-2H-pyran-4-yl group.
  • Salts of compound (I) are not particularly limited as long as they are agriculturally and horticulturally acceptable salts.
  • 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
  • salts of transition metals salts of organic bases such as triethylamine, tributylamine, pyridine and hydrazine
  • ammonium salts are not particularly limited as long as they are agriculturally and horticulturally acceptable salts.
  • 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
  • salts of transition metals salts of organic bases
  • salts of organic bases
  • the method for producing compound (I) or a salt thereof is not limited.
  • compound (I) or a salt thereof of the present invention can be obtained by known methods such as those described in Examples.
  • a salt of compound (I) can be obtained from compound (I) by a known method.
  • the agricultural and horticultural fungicide of the present invention contains as an active ingredient at least one selected from compound (I) and salts thereof.
  • the amount of compound (I) or a salt thereof contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it exhibits a fungicidal effect.
  • the agricultural and horticultural fungicides of the present invention are suitable for a wide variety of filamentous fungi such as Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, zygotes. It can be used to control plant diseases caused by fungi belonging to Zygomycetes.
  • Examples of plant diseases (pathogens) targeted for control are shown below.
  • Sugar beet brown spot (Cercospora beticola), cochlioides (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), spot Peanuts: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum ), rust (Alternaria alternata), white silk (Sclerotium rolfsii), black stain (Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc.
  • Cucumber powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis) , Mycosphaerella melonis, Fusarium oxysporum, Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum orbiculare, Cladosporium cucumerinum, Brown spot Corynespora cassiicola, Pythium debaryanum, Rhizoctonia solani Kuhn, Phomopsis sp., Pseudomonas syringae pv. Lachrymans, etc.
  • Tomatoes Botrytis cinerea, leaves Mold (Cladosporium fulvum), plague (Phytophthora infestans), wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), ring spot (Alternaria solani), Pseudocercospora fuligena, Ralstonia solanacearum, Sclerotinia sclerotiorum, etc.
  • Eggplant Botrytis cinerea, Corynespora melongenae, Erysiphe cichoracearum), Mycovellosiella nattrassii, Sclerotinia sclerotiorum, Verticillium dahliae, Phomopsis vexans, etc.
  • Pepper Phytophthora capsici, Botrytis cinerea , Sclerotinia sclerotiorum, Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense, Leveillula taurica
  • Botrytis cinerea Sphaerotheca humuli , Colletotrichum acutatum, Colletotrichum fragariae, Phytophthora cactorum, Rhizopus stolonifer, Fusarium oxysporum, Verticillium dahliae, Sclerotinia sclerotiorum, etc.
  • Onions Gray Botrytis allii, Botrytis cinerea, Botrytis squamosa, Peronospora destructor, Phytophthora porri, Ciborinia allii, Small fungi nucleus rot (Botrytis squamosa), dry rot (Fusarium oxysporum), red root rot (Pyrenochaeta terrestris), black rot sclerotium (Sclerotium cepivorum), rust (Puccinia allii), white silk disease (Sclerotium rolfsii), etc.
  • Green onions soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black rot (Sclerotium cepivorum), rust (Puccinia allii), leaf blight (Botrytis squamosa), white silk disease (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc.
  • Cabbage clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv.
  • campestris black spot (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), mildew (Peronospora parasitica), sclerotinia (Sclerotinia sclerotiorum) ), Black soot (Alternaria brassicicola), Gray mold (Botrytis cinerea), Root rot (Phoma lingam), Pythium aphanidermatum, Pythium ultimum, White rust (Albugo macrospora), etc.
  • Apples powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), monilia (Monilinia mali), black spot (Mycosphaerella pomi), rot (Valsa mali), leaf spot (Alternaria mali), scab (Gymnosporangium) yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena), purple leaf spot (Helicobasidium mompa), White leaf disease (Rosellinia necatrix), Gray mold (Botrytis cinerea), Fire blight (Erwinia amylovora), Silver leaf disease (Chondrostereum purpureum), Root canker
  • Grapes Botrytis cinerea, powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum) acutatum), downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), Snow white (pathogen unidentified), root cancer (Rhizobium radiobacter, Rhizobium vitis), etc.
  • Pear Venturia nashicola, Gymnosporangium asiaticum, Alternaria kikuchiana, Ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown spot (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: Pestalotiops is longiseta, P.
  • Kiwifruit Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava, Pseudomonas syringae, Botrytis cinerea, fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), Pseudocercospora actinidiae, etc.
  • Olive Colletotrichum acutatum, Colletotrichum gloeosporioides, eacock spot (Spilocaea oleaginea), etc.
  • Chestnut Colletotrichum gloeosporioides, etc.
  • Powdery mildew (Blumeria graminis f.sp. tritici), Fusarium head blight (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), Fusarium rust (Puccinia recondita), Yellow rust (Puccinia striiformis), Pythium iwayamai, Monographella nivalis, Pseudocercosporella herpotrichoides, Septoria tritici, Leptosphaeria nodorum, Typhula incarnata), Myriosclerotinia borealis, Gaeumannomyces graminis, Claviceps purpurea, Tilletia caries, Ustilago nuda, Pyricularia grisea ), Damping off (Pythium spp., Fusarium spp., Rhizoc
  • Rice Pyricularia oryzae, Rhizoctonia solani, Gibberella fujikuroi, Cochliobolus miyabeanus, Pythiumg raminicola), Xanthomonas oryzae, Burkholderia plantarii, Acidovorax avenae, Burkholderia glumae, Cercospora oryzae, Rice blight (Ustilaginoidea virens), Brown rice (Alternaria alternata, Curvularia intermedia), Alternaria padwickii, Epicoccum purpurascens, etc.
  • Tobacco Sclerotinia sclerotiorum, Erysiphe cichoracearum, plague ( Phytophthora nicotianae), etc.
  • Tulips Botrytis cinerea, Botrytis tulipae, Rhizoctonia solani, Fusarium oxysporum, Rhizoctonia solani, etc.
  • Rose Black star Diplocarpon rosae, powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc.
  • Peronospora danica Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum, Rhizoctonia solani, Fusarium solani, etc.
  • Gerbera Botrytis cinerea ), powdery mildew (Podosphaera xanthii), etc.
  • Lily leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc.
  • Sunflower downy mildew (Pla smopara halstedii), Sclerotinia sclerotiorum, Botrytis cinerea, etc.
  • Bent grass Sclerotinia borealis, large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), dollar spot ( Sclerotinia homoeocarpa), Pyricularia sp., Pythium aphanidermatum, Colletotrichum graminicola, etc.
  • Orchard grass Powdery mildew (Erysiphe graminis), etc.
  • Soybean Purpura (Cercospora kikuchii), downy mildew Peronospora manshurica, Phytophthora sojae, Phakopsora pachyrhizi, Sclerotinia sclerotiorum, Colletotrichum truncatum, Botrytis cinerea, Elsinoe glycines ), Black spot (Diaporthe phaseolorum var. sojae), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc.
  • Potatoes Phytophthora infestans ), Alternaria solani, Thanatephorus cucumeris, Verticillium albo-atrum, V. dahliae, V. nigrescens, Pectobacterium atrosepticum, Pectobacterium carotovorum, Gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia (Sclerotinia sclerotiorum), etc. sporium dioscoreae, Colletotrichum gloeosporioides, Penicillium sclerotigenum, etc. Sweet potato: Helicobasidium mompa, Fusarium oxysporum, etc.
  • Mango Anthracnose (Colletotrichum) aenigma), canker (Xanthomonas campestris), shaft rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), gray mold (Botrytis cinerea), etc.
  • Rapeseed Sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae), powdery mildew (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), downy mildew (Peronospora parasitica), etc.
  • Coffee rust (Hemileia vastatrix), anthracnose ( Coletotrichum coffeanum), brown eye disease (Cercospora coffeicola), etc.
  • Sugarcane Brown rust (Puccinia melanocephala), etc.
  • Hops Downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold disease (Botrytis cinerea), etc.
  • the nitrogen-containing heteroaryl compound of the present invention also has an excellent control effect against various nematodes that affect plant growth.
  • the nematicide of the present invention contains at least one selected from compound (I) and salts thereof as an active ingredient.
  • the amount of compound (I) or a salt thereof contained in the nematicide of the present invention is not particularly limited as long as it exhibits a nematode control effect.
  • Tylenchida (a) Anguinidae, for example, Anguina spp., Anguina funesta, Anguina tritici; Ditylenchus spp., Imogusare nematode ( Ditylenchus destructor), Namiki Nematode (Ditylenchus dipsaci), Mushroom Nematode (Ditylenchus myceliophagus); (b) Aphelenchoides family (Aphelenchoididae), for example, Aphelenchoides spp., Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi; Bursaphelenchus xylophilus, of the genus Bursaphelenchus spp.; (c) Belonolaimida
  • Globodera spp. Heterodera spp.
  • Heterodera spp. Heterodera avenae, Heterodera cruciferae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii
  • Hoplolimidae for example, Helicotylenchus spp., Helicotylenchus dihystera, Helicotylenchus multicinctus; Columbus (Hoplolaimus columbus), Hoplolaimus galeatus; Others, Rotylenchus robustus, Rotylenchus reniformis
  • Platylenchus brachyurus Pratylenchus coffeae, Pinnematode (Pratylenchus curvitatus) ), Pratylenchus fallax, Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Platylenchus scribneri, Rumi-negative nematode (Pratylenchus vulnus), sorghum nematode (Pratylenchus zeae); others, root-knot nematode (Nacobbus aberrans), banana leaf nematode (Radopholus similis), orange nematode (Tylenchulus semipenetrans), citrus nematode (Radopholus) citrophilus).
  • Dorylaimida (a) Longidoridae, e.g., Longidorus spp., Longidorus elongates; Xiphinema, Xiphinema americanum, Xiphinema brevicole (Xiphinema brevicolle), Grape Nematode (Xiphinema index), Xiphinema diversicaudatum (Xiphinema diversicaudatum).
  • Triplonchida (a) Trichodoridae family (Trichodoridae), for example, Trichodorus monibus (Trichodorus planibus), Nematode nematode (Paratrichodorus minor).
  • the agricultural and horticultural fungicides or nematicides of the present invention are grains; vegetables; root vegetables; potatoes; fruit trees, tea, coffee, trees such as cacao; It is preferably used for
  • the agricultural and horticultural fungicide of the present invention can be applied to various parts of plants, such as leaves, stems, stems, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots and cuttings. .
  • Nematicides can be applied to roots, tubers, root tubers, and the like.
  • improved cultivars/varieties, cultivated cultivars, mutants, hybrids, and genetically modified organisms (GMO) of these plants can also be targeted.
  • the agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. for the control of various diseases occurring in agricultural and horticultural crops including flowers, lawns, and pastures. can be done.
  • Nematicides can be used in seed treatments, soil applications, and the like.
  • the agricultural and horticultural fungicide or nematicide of the present invention may contain components other than the nitrogen-containing heteroaryl compound of the present invention.
  • Other components include known carriers used for formulation. Examples of other components include conventionally known fungicides, insecticides/miticides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds, and the like. be able to. A synergistic effect may be produced by containing such other components.
  • one aspect of the present invention is an agricultural and horticultural fungicide containing one or more additional fungicides.
  • nucleic acid biosynthesis inhibitors (a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl; (b) adenosine deaminase inhibitors: bupirimate, dimethylmol, ethylimol; (c) DNA/RNA synthesis inhibitors: Hymexazole, Octilinone; (d) DNA topoisomerase II inhibitor: oxolinic acid.
  • mitotic inhibitors and cytostatic agents (a) beta-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; diethofencarb; zoxamide; ethaboxam; (b) a cytostatic agent: pencicron; (c) delocalized inhibitors of spectrin-like proteins: fluopicolide, fluopimimide.
  • respiratory inhibitors (a) complex I-NADH oxidoreductase inhibitors: diflumetrim; tolfenpyrad; (b) complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil; isofetamide; fluopyram; fenfuram, flumeciclox; carboxin, oxycarboxin; sado, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid, pydiflumetofen, isoflurcipram, pyraziflumide, inpyrfluxam; (c) complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, comoxistrobin, cumethoxstrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin , pyrametostrobin, triclo
  • amino acid and protein synthesis inhibitors (a) methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil; (b) protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.
  • signaling inhibitor (a) signaling inhibitors: quinoxifene, proquinazide; (b) MAP and histidine kinase inhibitors in osmotic signaling: fenpicronil, fludioxonil; clozolinate, iprodione, procymidone, vinclozolin.
  • Lipid and Cell Membrane Synthesis Inhibitors (a) phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos; isoprothiolane; (b) lipid peroxidants: biphenyl, chloroneb, dichlorane, quintozene, technazene, tolclofos-methyl; etridiazole; (c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb.
  • cell membrane sterol biosynthesis inhibitors (a) C14 Demethylation Inhibitors in Sterol Biosynthesis: Trifolin; Pyrifenox, Pyrisoxazole; Fenarimol, Flurprimidol, Nuarimol; Imazalil, Imazalil Sulfate, Oxpoconazole, Pefurazoate, Prochloraz, Triflumizole , biniconazole; azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, pencon
  • cell wall synthesis inhibitor (a) a trehalase inhibitor: validamycin; (b) chitin synthase inhibitors: polyoxins, polyoxolims; (c) cellulose synthase inhibitors: dimethomorph, flumorph, pirimorph; bentiavaricarb, iprovalicarb, valifenalate; mandipropamide.
  • melanin biosynthesis inhibitors (a) reductase inhibitors of melanin biosynthesis: fthalide; pyroquilone; tricyclazole; (b) dehydratase inhibitors of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl; (c) polyketide synthesis inhibitor of melanin biosynthesis: tolprocarb.
  • Agents of unknown activity cymoxanil, fosetylaluminum, phosphoric acid (phosphate), tecloftalam, triazoxide, fursulfamide, diclomedine, metasulfocarb, cyflufenamide, metrafenone, pyriophenone, dodine, dodine free base, flutianil.
  • agents with multiple sites of action copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; mannkapper, metiram, polycarbamate, propineb, thiram, zineb, ziram; captan, captafol, folpet; chlorothalonil; silates (iminoctadine trialbesilate); anilazine; dithianone; quinomethionate; fluorimide.
  • Biological/biological pesticides with multiple mechanisms of action extract from the cotyledons of lupine plantlets; extract from Swinglea glutinosa; (tea tree) extract from Melaleuca alternifolia (tea tree oil); plant oils (mixtures): eugenol, geraniol, thymol.
  • Trichoderma atroviride strain I-1237 Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1 (Trichoderma atroviride strain SC1), Trichoderma atroviride strain SKT-1 strain (Trichoderma atroviride strain SKT-1), Trichoderma atroviride strain 77B strain (Trichoderma atroviride strain 77B); Trichoderma asperellum strain T34, Trichoderma asperellum strain kd; Trichoderma harzianum T-22 strain (Trichoderma harzianum strain T-22); Trichoderma virens strain G-41; Gliocladium catenulatum J1446 strain (Gliocladium catenulatum strain J1446); Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON/M/91-08; Talaromyces flavus strain SA
  • Acetylcholinesterase (AChE) inhibitor (carbamate): alanicarb, aldicarb, bendiocarb, benfuracarb, butocaboxim, butoxycarboxim, carbaryl, carbofuran, carbosulphan, ethiophenecarb, phenocarb, formethanate, furatiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, Thiophanox, triazamate, trimetacarb, XMC, xylylcarb.
  • AChE Acetylcholinesterase
  • Acetylcholinesterase (AChE) inhibitors organophosphorus: Acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, cassafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, dimethone-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfotone, EPN, Ethion, Etprophos, Fanfur, Fenamiphos, Fenitrothion, Fenthion, Hostthiazate, Heptenophos, Imisiaphos, Isofenphos, Isopropyl O-(methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos
  • GABAergic chloride ion (chloride ion) channel blockers Chlordane, Endosulfan; Ethiprole, Fipronil. Flufiprol.
  • ⁇ -Bifenthrin Chloroprathrin, Heptafluthrin, Meperfluthrin, ⁇ -Metofluthrin, Monfluorothrin, ⁇ -Monfluorothrin, ⁇ -Tefluthrin, Tetramethylfluthrin; Bioethanomethrin.
  • DDTs Sodium channel modulators
  • Nicotinic acetylcholine receptor (nAChR) competitive modulators Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; Nicotine; Sulfoxaflor; Flupyradifuron; Triflumesopyrim. Dichloromesotiaz, flupyrimine.
  • Glutamatergic chloride (chloride) channel (GluCl) allosteric modulators Abamectin, Emamectin, Emamectin Benzoate, Lepimectin, Milbemectin. Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin. (7) juvenile hormone-like agents: Hydroprene, Quinoprene, Methoprene; Fenoxycarb; Pyriproxyfen.
  • Mites growth inhibitor Clofentezine, Diflovidazine, Hexythiazox; Etoxazole.
  • Microorganism-derived insect midgut lining-disrupting agent israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. Bacillus sphaericus.
  • Mitochondrial ATP synthase inhibitor diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide; propargite; tetradifon.
  • Oxidative phosphorylation uncouplers that perturb the proton gradient Chlorfenapyr, DNOC, sulflumide.
  • Nicotinic Acetylcholine Receptor (nAChR) Channel Blockers bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt.
  • Chitin biosynthesis inhibitor, type 0 bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.
  • chitin biosynthesis inhibitor type 1: buprofezin.
  • molting inhibitor Cyromazine.
  • molting hormone (ecdysone) receptor agonists Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.
  • Octopamine receptor agonists Amitraz.
  • mitochondrial electron transport chain complex III inhibitor hydramethylnon; acequinosyl; fluacrypyrim; bifenazate.
  • mitochondrial electron transport chain complex I inhibitor (METI): Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad; Rotenone.
  • voltage-gated sodium channel blockers indoxacarb; metaflumizone.
  • Acetyl-CoA carboxylase inhibitors Spirodiclofen, spiromesifen, spirotetramat. spiropidion.
  • mitochondrial electron transport chain complex IV inhibitor Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine; calcium cyanide, sodium cyanide, potassium cyanide.
  • mitochondrial electron transport chain complex II inhibitor cyenopyrafen, cyflumetofen; piflubumide.
  • ryanodine receptor modulators Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Flubendiamide. Cyhalodiamide, tetrachlorane traniliprole, tetraniliprole.
  • GABAergic chloride ion (chloride) channel allosteric modulators Brofuranilide, Fluxametamide. Isocycloseram; afoxolaner, fluralaner, rotineral, sarolaner. Other insecticides and acaricides: Azadirachtin, benzoximate, bromopropylate, quinomethionate, dicofol, lime-sulfur mixture, mancozeb, pyridalyl, sulfur. Acinonapyr, benzpyrimoxane, flometoquine, fluhexafone, oxazosulfil, ticlopyrazofrole.
  • Anthelmintic (a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimine, thiophanate; thiabendazole, cambendazole; (b) Salicylanilides: Closantel, Oxyclozanide, Rafoxanide, Niclosamide; (c) substituted phenolics: nitroxynil, nitroscanate; (d) pyrimidine series: pyrantel, morantel; (e) imidazothiazoles: levamisole, tetramisole; (f) tetrahydropyrimidines: praziquantel, epsiprantel; (g) Other anthelmintics: cyclodiene, liania, clorsulon, metronidazole, demidi
  • plant regulators that can be mixed or used together with the agricultural and horticultural fungicide or nematicide of the present invention are shown below. Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, horchlorfenurone, thidiazuron, chlorfenurone, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -naphthylacetamide, ethiclozate, cloxyhonac, maleic hydrazide, 2,3,
  • the agricultural and horticultural fungicide or nematicide of the present invention includes the compound (I) of the present invention and a salt thereof, other active ingredients and agricultural and horticulturally acceptable auxiliary ingredients for formulation (for example, , inorganic carriers, organic carriers, surfactants, solvents, etc.) can be added.
  • the agricultural and horticultural fungicide or nematicide of the present invention is not particularly limited by its dosage form.
  • dosage forms such as wettable powders, emulsions, powders, granules, aqueous solutions, suspensions, wettable powders, and tablets can be mentioned.
  • the preparation method for the formulation is not particularly limited, and a known preparation method can be adopted depending on the dosage form.
  • the nitrogen-containing heteroaryl compound of the present invention can be used as a prophylactic or therapeutic agent for controlling harmful pathogens, especially fungi, that infect humans or animals.
  • the medical/veterinary antifungal agent of the present invention contains at least one selected from compound (I) and salts thereof as an active ingredient.
  • the amount of compound (I) or a salt thereof contained in the medical antifungal agent of the present invention is not particularly limited as long as the antifungal effect is exhibited.
  • animal refers to pets, livestock and poultry, animals raised in zoos and aquariums, captured wild animals, and vertebrates such as research and experimental animals (Vertebrates) means r a t a).
  • Examples include the following animals, but specific examples of animals are not limited to these. sheep, goat, pig, horse, cow, buffalo, donkey, mule, camel, llama, alpaca, wild boar, reindeer, deer, mink, elephant, bear, kangaroo, fox, dog, cat, squirrel, rabbit, mouse, rat, Mammals such as guinea pigs, hamsters, monkeys and ferrets.
  • Birds such as pigeons, parakeets, parrots, sparrows, marigolds, canaries, chickens, ducks, turkeys, ducks, pheasants, peacocks, ostriches, swans, sparrows, quail, owls, eagles, hawks, and cormorants.
  • Reptiles such as chameleons, iguanas, lizards, snakes, turtles, crocodiles and geckos.
  • Amphibians such as frogs and newts. Fish such as carp, goldfish, killifish, tropical fish, yellowtail, yellowtail, sea bream, amberjack, salmon, mackerel, sea bass, longtooth grouper, tuna, horse mackerel, flounder, and blowfish.
  • fungi examples are shown below as pathogenic bacteria to which the medical and veterinary antifungal agent of the present invention can be applied.
  • Alternaria genera such as Alternaria alternata; Aspergillus genera such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, Aspergillus parasiticus, Aspergillus terreus; Bipolaris genera; Blastomyces genera such as Blastomyces dermatitidis ; Blumeria genus such as Blumeria graminis; Candida genus such as Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, and Candida tropicalis; Cladosporium genus such as Cladosporium cladosporoides and Cladosporium herbarium; Cryptococcus genera such as Cryptococcus neoformans; Curvul
  • mycoses are shown below as infectious diseases to which the medical and veterinary antifungal agent of the present invention can be applied. However, specific examples are not limited to these.
  • the medical/veterinary antifungal agent of the present invention can be applied to both systemic fungal infections and superficial fungal infections.
  • fungal infections include Aspergillus diseases such as pulmonary aspergillosis, systemic aspergillosis (which is more likely to occur in immunosuppressed patients such as bone marrow recipients or AIDS patients), Candida diseases such as systemic candidiasis ( Candida disease, Cryptococcus meningitis, rhinocerebral mucomycosis, pulmonary mucormycosis, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, robomycosis, Keratomycosis, sporotrichosis, chromoblastomycosis, chromomycosis, pheophyphomycosis, zygomycosis, cryptococcosis, disseminated sporotrichosis, ring worm, tinea capitis, tinea corp
  • the medical/veterinary antifungal agent of the present invention can contain pharmaceutically acceptable additives.
  • Additives are not particularly limited as long as they are used in known medical drugs. They are of course sterile and non-pyrogenic.
  • the additive can be appropriately selected according to the dosage form and administration method of the antifungal agent.
  • the dosage form that the medical/veterinary antifungal agent of the present invention can take is not particularly limited. , emulsions, suspensions, solutions, drops (Pour-on), spot-on, etc.; semi-solid preparations such as ointments, gels, etc.; aerosols, vapors, etc. Gaseous agents; nanoparticle formulations and the like can be mentioned.
  • Administration of the medical antifungal agent of the present invention can be performed by known methods. Examples of administration methods include subcutaneous, intravenous, intramuscular, intrasternal injection (injection); insertion into the anus, vagina, etc.; oral administration such as oral administration; nasal administration such as inhalation.
  • additives that can be used in the medical and veterinary antifungal agents of the present invention include solubilizers such as cyclodextrins or modified cyclodextrins; lactose, dextrose, sucrose, cellulose, cornstarch or Diluents such as potato starch; Lubricants such as silica, talc, stearic acid, magnesium or calcium stearate, polyethylene glycol; Binding agents such as starch, arabic gums, gelatin, methylcellulose, carboxymethylcellulose or polyvinylpyrrolidone.
  • solubilizers such as cyclodextrins or modified cyclodextrins
  • lactose dextrose, sucrose, cellulose, cornstarch or Diluents
  • Lubricants such as silica, talc, stearic acid, magnesium or calcium stearate, polyethylene glycol
  • Binding agents such as starch, arabic gums, gelatin, methylcellulose
  • disaggregating agents such as starch, alginic acid, alginates or sodium starch glycolate; effervescing mixtures; dyes; sweeteners;
  • effervescing mixtures dyes; sweeteners;
  • non-toxic and pharmacologically inactive substances generally used in pharmaceutical formulations can be used.
  • additives can be incorporated into the medical antifungal agent of the present invention by known methods such as mixing, granulation, tableting, sugar coating, or film coating.
  • additives that can be used in the medical and veterinary antifungal agents of the present invention include solubilizers such as cyclodextrins or modified cyclodextrins, saccharose, glycerin, mannitol, sorbitol, natural gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, polyvinyl alcohol, and the like.
  • the additives that can be used in the medical and veterinary antifungal agent of the present invention include sterilized water, olive oil, ethyl oleate, glycols such as propylene glycol, cyclodextrin, and modified cyclodextrins. Dissolution aids such as dextrin can be used. Furthermore, an appropriate amount of lidocaine hydrochloride can be included as necessary.
  • the amount of compound (I) or a salt thereof contained in the medical or veterinary antifungal agent of the present invention is preferably 85% by weight or less, more preferably 50% by weight or less, based on the weight of the antifungal agent. .
  • the dose of the medical/veterinary antifungal agent of the present invention can be appropriately selected according to the administration method, the type of fungi infected, the patient's age, body weight, symptoms, and the like. For example, in the case of oral or parenteral (injection, infusion, etc.) administration to adults, it can be administered at 0.1 to 100 mg/kg-body weight once or several times a day.
  • the medical and veterinary antifungal agents of the present invention can be used in combination with drugs other than compound (I).
  • Step 2 2-(3-bromo-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide Synthesis of 2-(5-bromo-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide (0.80 g) was dissolved in N,N-dimethylformamide (20 ml), and 1-ethynyl-2-methoxybenzene (0 .60 g), triethylamine (12 ml), copper (I) iodide (0.09 g) and bis(triphenylphosphine)palladium (II) dichloride (0.30 g) were added and stirred at 80° C.
  • Step 5 Synthesis of 2-(3-acetyl-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
  • 2-(3-bromo-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide (0.32 g) was dissolved in 1,4-dioxane (5 ml), tributyl(1-ethoxyvinyl)stannane (0.37 g), bis(triphenylphosphine) palladium (II) dichloride (0.06 g) were added, It was heated to reflux for 2 hours.
  • the reaction solution was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate), the obtained product was dissolved in tetrahydrofuran (5 ml), 4N aqueous hydrogen chloride solution (1.5 ml) was added, and the temperature was raised to 50°C. and stirred for 4 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 0.21 g of the desired compound.
  • Step 6 Synthesis of (E)-2-(3-(1-(isopropoxyimino)ethyl)-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
  • 2-(3-acetyl-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide (0.09 g) was dissolved in ethanol (2 ml) and chloroform (2 ml), and pyridine (0.04 g) and 2-(aminooxy)propane hydrochloride (0.05 g) were added and stirred at room temperature for 1 hour.
  • step 2 N-((2S)-1-(5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-((E)-1-isopropoxyimino)ethyl)-2-oxopyridin-1( Synthesis of 2H)-yl)propan-2-yl)isobutyramide (step 1) Synthesis of (E)-1-(5-bromo-2-methoxypyridin-3-yl)ethan-1-one O-isopropyl oxime 1-(5-bromo-2-methoxypyridin-3-yl)ethan-1-one (1.0 g) was dissolved in ethanol (15 ml), 2-(aminooxy) propane hydrochloride (0.55 g) was added, and the mixture was warmed to room temperature.
  • Step 2 Synthesis of (E)-1-(5-fluoro-2-methoxyphenyl)-2-(5-(1-(isopropoxyimino)ethyl)-6-ethoxypyridin-3-yl)ethan-1-one
  • a solution obtained by dissolving 1-(5-fluoro-2-methoxyphenyl)ethan-1-one in 1,4-dioxane (5 ml) was added to a 1.3 M lithium (bistrimethylsilyl)amide tetrahydrofuran solution (15 ml).
  • Step 3 Synthesis of (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-3-(1-(isopropoxyimino)ethyl)pyridin-2(1H)-one
  • E)-1-(5-fluoro-2-methoxyphenyl)-2-(5-(1-(isopropoxyimino)ethyl)-6-methoxypyridin-3-yl)ethan-1-one (1.30 g) , N-dimethylformamide (8 ml), p-toluenesulfonic acid monohydrate (2.50 g) and lithium chloride (0.55 g) were added, and the mixture was stirred at 70°C for 2 hours.
  • Step 4 Synthesis of (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-(1-(isopropoxyimino)ethyl)pyridin-2(1H)-one
  • Step 5 N-((2S)-1-(5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-((E)-1-(isopropoxyimino)ethyl)-2-oxopyridin-1 Synthesis of (2H)-yl)propan-2-yl)isobutyramide (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-(1isopropoxyimino)ethyl)pyridin-2(1H)-one (0.33 g) was added to N,N-dimethyl It was dissolved in formamide (4 ml), cesium carbonate (0.40 g) and (S)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate (0.45 g) were added, and the mixture was stirred at 70°C for 4 hours.
  • the solvent was distilled off under reduced pressure, a saturated aqueous sodium hydrogencarbonate solution was added, the extract was extracted with chloroform, washed with water and saturated brine, and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in N,N-dimethylformamide (50 ml). Stir at °C for 6 hours. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, extracted with chloroform, and dried over anhydrous sodium sulfate.
  • Step 2 Synthesis of 5-bromo-1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime 1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime (6.50 g) was dissolved in methanol (30 ml), tetrahydrofuran ( 30 ml), sodium borohydride (600 mg) was added under ice-cooling, and the mixture was stirred for 10 minutes.
  • a saturated aqueous ammonium chloride solution was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in methylene chloride (80 ml), N-bromosuccinimide (3.30 g) was added, and the mixture was stirred at room temperature for 4 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate.
  • Step 3 Synthesis of methyl2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((isopropoxyimino)methyl)-4-oxo-1,4-dihydropyridin-3-yl)benzoate 5-bromo-1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime (1.0 g) - dioxane (25 ml), dissolved in water (3 ml), dichlorobis[di-t-butyl(4-dimethylaminophenyl)]phosphine]paradylum (II) (0.20 g), potassium carbonate (0.70 g), 2- (Methoxycarbonyl)phenylboronic acid (0.70 g) was added, and the mixture was heated under reflux for
  • Tables 1 and 2 show some of the nitrogen-containing heteroaryl compounds produced in the same manner as in the above Examples.
  • the table also shows the melting point (°C) or physical properties of each compound as physical properties.
  • Table 3 shows the 1 H-NMR data of some of the compounds in the table.
  • Tables 4 and 5 show retention times in liquid chromatography-mass spectrometry (LCMS) for some of the compounds in the table.
  • the concentration of the mobile phase (B) is increased from 30% by mass to 95% by mass with a linear gradient of 1.5 minutes, and (II) is maintained at 95% by mass for 0.5 minutes, (III) Immediately lowered to 30% by weight (B) and (IV) maintained at 30% by weight for 0.50 minutes.
  • Table 6 shows some of the nitrogen-containing heteroaryl compounds.
  • the table also shows the melting point (°C) or physical properties of each compound as physical properties. Some compounds were also shown to be isomeric mixtures.
  • LCMS liquid chromatography mass spectrometry
  • Electrophoresis was performed on ACQUITY UPLC H-Class (Waters) using an ACQUITY UPLC photodiode array (PDA) e ⁇ detector (Waters) and an ACQUITY QDa detector (in positive and negative ion electrospray mode, UV PDA). Detection, manufactured by Waters Co., Ltd.), and Method (A) or Method (B) shown below was used.
  • test emulsion 5 parts by weight of the nitrogen-containing heteroaryl compound of the present invention, 93.5 parts by weight of N,N-dimethylformamide, and 1.5 parts by weight of polyoxyethylene sorbitan monolaurate (TWEEN (registered trademark) 20) were mixed and dissolved. to give an emulsion (I) containing 5% active ingredient.
  • TWEEN polyoxyethylene sorbitan monolaurate
  • the control value was calculated using the following formula.
  • Control value (%) 100- ⁇ lesion area ratio in treated area / lesion area ratio in untreated area ⁇ ⁇ 100
  • A-7, A-8, A-9, A-11, A-16, A-22, A-23, A-28, A-31, A-32, A-33, A-34, a- 3, a-4, and a-11 were subjected to an apple scab control test. All compounds showed a control value of 75% or more.

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Abstract

The present invention addresses the problem of providing: a nitrogen-containing heteroaryl compound which exhibits excellent bactericidal and anti-bacterial activity and excellent safety and which can be synthesized in an industrially advantageous manner; and an agricultural and horticultural anti-bacterial agent containing same as an active ingredient.　This nitrogen-containing heteroaryl compound is a compound represented by formula (I-1), formula (I-2) or formula (I-3), or a salt of these.　In formula (I-1), formula (I-2) and formula (I-3): Y1 denotes an oxygen atom or a sulfur atom; X1, X2 and X4 each independently denote a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or the like; X3 denotes a hydrogen atom, a substituted or unsubstituted straight chain C1-6 alkyl group, a substituted or unsubstituted straight chain C2-6 alkenyl group, or the like; B denotes a single bond, an oxygen atom, or the like; A denotes a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, or the like; and Q denotes a substituted or unsubstituted C6-10 aryl group or a heterocyclyl group of a substituted or unsubstituted 5- to 10-membered ring.

Description

含窒素ヘテロアリール化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤Nitrogen-containing heteroaryl compounds, agricultural and horticultural fungicides, nematicides, and medical and veterinary antifungal agents
　本発明は、含窒素ヘテロアリール化合物および農園芸用殺菌剤に関する。より詳細に、本発明は、殺菌・抗菌活性に優れ、安全性に優れ、且つ工業的に有利に合成できる含窒素ヘテロアリール化合物、並びにこれを有効成分として含有する農園芸用殺菌剤に関する。さらに、前記の化合物を有効成分として含有する殺線虫剤に関する。さらに、前記の化合物を有効成分として含有する医療用・動物用抗真菌剤に関する。
　本願は、２０２１年４月２３日に出願された日本国特許出願第２０２１-０７３１２３号、２０２１年８月１３日に出願された日本国特許出願第２０２１-１３１９４６号及び２０２１年１０月６日に出願された日本国特許出願第２０２１-１６５０９８号に対し優先権を主張し、その内容をここに援用する。 TECHNICAL FIELD The present invention relates to nitrogen-containing heteroaryl compounds and agricultural and horticultural fungicides. More specifically, the present invention relates to a nitrogen-containing heteroaryl compound that has excellent bactericidal and antibacterial activity, is excellent in safety, and can be industrially advantageously synthesized, and an agricultural and horticultural fungicide containing the same as an active ingredient. Furthermore, it relates to a nematicide containing the above compound as an active ingredient. Furthermore, it relates to medical and veterinary antifungal agents containing the above compounds as active ingredients.
This application is based on Japanese Patent Application No. 2021-073123 filed on April 23, 2021, Japanese Patent Application No. 2021-131946 filed on August 13, 2021 and on October 6, 2021 A priority is claimed with respect to the Japanese patent application No. 2021-165098 which was filed, and the content is used here.
　農園芸作物の栽培に当り作物の病害に対して防除活性を有する化合物が種々提案されている。そのような化合物を農園芸用殺菌剤として実用するためには、効力が十分に高いだけでなく、薬剤抵抗性が生じ難いこと、植物に対する薬害や土壌汚染を生じさせないこと、家畜や魚類などに対する毒性が低いことなどが要求される。 Various compounds with control activity against crop diseases have been proposed for the cultivation of agricultural and horticultural crops. In order for such compounds to be practically used as agricultural and horticultural fungicides, they must not only have sufficiently high efficacy, but also must be resistant to drug resistance, not cause chemical damage or soil contamination to plants, and must be effective against livestock and fish. Low toxicity is required.
　ところで、特許文献１には、式（Ａ）で表される化合物などが開示されている。
Figure JPOXMLDOC01-appb-C000002
 By the way, Patent Literature 1 discloses a compound represented by the formula (A) and the like.
Figure JPOXMLDOC01-appb-C000002
ＷＯ　２０１３／０７１１６９　ＡWO 2013/071169A
　本発明の課題は、殺菌・抗菌活性に優れ、安全性に優れ、且つ工業的に有利に合成できる含窒素ヘテロアリール化合物、およびこれ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である。さらには、前記の化合物を有効成分として含有する殺線虫剤を提供することにある。さらには、前記の化合物を有効成分として含有する医療用・動物用抗真菌剤を提供することにある。 An object of the present invention is to provide a nitrogen-containing heteroaryl compound that has excellent bactericidal and antibacterial activity, is excellent in safety, and can be industrially advantageously synthesized, and an agricultural and horticultural fungicide containing this as an active ingredient. be. A further object is to provide a nematicide containing the above compound as an active ingredient. A further object of the present invention is to provide medical and veterinary antifungal agents containing the aforementioned compounds as active ingredients.
　本発明者らは、上記課題を解決すべく鋭意検討した結果、以下の態様を包含する本発明を完成するに至った。 As a result of intensive studies aimed at solving the above problems, the present inventors have completed the present invention including the following aspects.
　〔１〕　式（Ｉ－１）で表される化合物、式（Ｉ－２）で表される化合物、若しくは式（Ｉ－３）で表される化合物またはそれらの塩。
Figure JPOXMLDOC01-appb-C000003
 〔式（Ｉ－１）、式（Ｉ－２）、および式（Ｉ－３）中、
　Ｙ１は、酸素原子または硫黄原子を示し；
　Ｘ１、Ｘ２、およびＸ４は、それぞれ独立に、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基、またはＲ１Ｏ－Ｎ＝ＣＲ６－で表される基を示し；
　Ｒ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ２は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ３は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ４は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示し、
　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよく、
　Ｒ５は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒ６は、水素原子、ハロゲノ基、アミノ基、置換若しくは無置換のモノＣ１～６アルキルアミノ基、置換若しくは無置換のジＣ１～６アルキルアミノ基、置換若しくは無置換のＣ１～６アルキル基、置換もしくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し；
　Ｘ３は、水素原子、ハロゲノ基、置換若しくは無置換の直鎖Ｃ１～６アルキル基、置換若しくは無置換の直鎖Ｃ２～６アルケニル基、置換若しくは無置換の直鎖Ｃ２～６アルキニル基、Ｒ１－ＣＯ－で表される基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換の４～６員環のヘテロシクリル基、ＲＮ１Ｏ－で表される基、ＲＮ１－ＣＯ－Ｏ－で表される基、ＲＮ１－Ｏ－ＣＯ－Ｏ－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－Ｏ－で表される基、ＲＮ１－ＣＳ－Ｏ－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＳ－Ｏ－で表される基、ＲＮ１ＲＮ２Ｎ－で表される基、ＲＮ１－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－ＣＯ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－Ｏ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－ＣＳ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＳ－ＮＲＮ２－で表される基、ＲＮ１ＳＯ２－ＮＲＮ２－で表される基、またはＲＮ１－Ｃ（＝ＮＲＮ１）－ＮＲＮ２－で表される基を示し、
　ＲＮ１、およびＲＮ２は、それぞれ独立に、水素原子、置換若しくは無置換の直鎖Ｃ１～６アルキル基、置換若しくは無置換の直鎖Ｃ２～６アルケニル基、置換若しくは無置換の直鎖Ｃ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の４～６員環のヘテロシクリル基を示し、ここで、ＲＮ１とＲＮ１、またはＲＮ１とＲＮ２は、一緒になって二価の有機基を形成してもよく；
Ｂは、単結合、酸素原子、硫黄原子、スルフィニル基、スルホニル基、または－ＮＲＮ３－で表される基を示し、ＲＮ３は、水素原子、置換若しくは無置換のＣ１～６アルキル基、ホルミル基、または置換若しくは無置換のＣ１～６アルキルカルボニル基を示し；
　Ａは、置換若しくは無置換のＣ１～６アルキレン基、置換若しくは無置換のＣ２～６アルケニレン基、置換若しくは無置換のＣ２～６アルキニレン基、または置換若しくは無置換のＣ３～６シクロアルキレン基を示し；
Ｑは、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～１０員環のヘテロシクリル基を示す。〕
〔２〕Ｘ２が、Ｒ１Ｏ－Ｎ＝ＣＲ６－で表される基である、〔１〕に記載の化合物またはそれらの塩。
〔３〕〔１〕または〔２〕に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する農園芸用殺菌剤。
〔４〕種子処理用である、〔３〕に記載の農園芸用殺菌剤。
〔５〕〔１〕または〔２〕に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する殺線虫剤。
〔６〕〔１〕または〔２〕に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する医療用・動物用抗真菌剤。 [1] A compound represented by formula (I-1), a compound represented by formula (I-2), a compound represented by formula (I-3), or a salt thereof.
Figure JPOXMLDOC01-appb-C000003
 [In formula (I-1), formula (I-2), and formula (I-3),
Y 1 represents an oxygen atom or a sulfur atom;
X 1 , X 2 and X 4 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2- 6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group , substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5- to 6-membered heterocyclyl group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, nitro group, cyano group, R 1 —CO— a carboxy group, a group represented by R 2 —O—CO—, a group represented by R 3 R 4 N—, a group represented by R 3 R 4 N—CO—, R 1 — a group represented by CO—O—, a group represented by R 1 —CO—NR 5 —, a group represented by R 2 —O—CO—O—, and R 2 —O—CO—NR 5 — A group represented by R 3 R 4 N—CO—O— A group represented by R 3 R 4 N—CO—NR 5 — R 2 SO 2 —NR 5 — a group represented by R 3 R 4 N--SO 2 -- or a group represented by R 1 ON=CR 6 --;
R 1 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R 2 is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R 3 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
each R 4 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
wherein R 3 and R 4 may together form a divalent organic group,
each R 5 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R 6 is a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group;
X 3 is a hydrogen atom, a halogeno group, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R a group represented by 1 -CO-, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4- to 6-membered heterocyclyl group, R N1 O A group represented by -, a group represented by R N1 --CO--O--, a group represented by R N1 --O--CO--O--, a group represented by R N1 R N1 N--CO--O-- , a group represented by R N1 -CS-O-, a group represented by R N1 R N1 N-CS-O-, a group represented by R N1 R N2 N-, R N1 -CO-NR N2 - A group represented by R N1 —CO—CO—NR N2 — A group represented by R N1 —O—CO—NR N2 — R N1 R N1 N—CO—NR N2 — A group represented by R N1 R N1 N—CO—CO—NR N2 — A group represented by R N1 —CS-NR N2 — R N1 R N1 N—CS-NR N2 — a group represented by R N1 SO 2 —NR N2 — or a group represented by R N1 —C(=NR N1 )—NR N2 —,
R N1 and R N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R N1 and R N1 , or R N1 and R N2 may together form a divalent organic group;
B is a single bond, an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR N3 -, where R N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, formyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group;
A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group. ;
Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group. ]
[2] The compound or a salt thereof according to [1], wherein X 2 is a group represented by R 1 ON=CR 6 -.
[3] An agricultural and horticultural fungicide containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] or [2] and salts thereof.
[4] The agricultural and horticultural fungicide of [3], which is for seed treatment.
[5] A nematicide containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] or [2] and salts thereof.
[6] A medical or veterinary antifungal agent containing, as an active ingredient, at least one selected from the group consisting of the compounds of [1] or [2] and salts thereof.
　本発明の含窒素ヘテロアリール化合物は、殺菌・抗菌活性に優れ、効果が確実で、安全性に優れ、且つ工業的に有利に合成できる。
　本発明の農園芸用殺菌剤及び殺線虫剤は、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。
　本発明の医療用・動物用抗真菌剤は、優れた抗菌効果を有し、人畜魚類に対する毒性が少ない。 The nitrogen-containing heteroaryl compound of the present invention is excellent in bactericidal and antibacterial activity, has a reliable effect, is excellent in safety, and can be industrially advantageously synthesized.
The agricultural and horticultural fungicide and nematicide of the present invention have an excellent control effect, do not cause phytotoxicity to plants, and are less toxic to humans, livestock and fish, and have less impact on the environment.
The medical and veterinary antifungal agents of the present invention have excellent antibacterial effects and are less toxic to humans, animals, and fish.
〔含窒素ヘテロアリール化合物〕
　本発明の含窒素ヘテロアリール化合物は、式（Ｉ－１）で表される化合物、式（Ｉ－２）で表される化合物、若しくは式（Ｉ－３）で表される化合物（以下、化合物（Ｉ）と表記することがある。）または化合物（Ｉ）の塩である。
Figure JPOXMLDOC01-appb-C000004
 [Nitrogen-containing heteroaryl compound]
The nitrogen-containing heteroaryl compound of the present invention is a compound represented by formula (I-1), a compound represented by formula (I-2), or a compound represented by formula (I-3) (hereinafter, compound (I)) or a salt of compound (I).
Figure JPOXMLDOC01-appb-C000004
　本発明において、用語「無置換（unsubstituted）」は、母核となる基のみであることを意味する。母核となる基の名称のみで記載しているときは、別段の断りがない限り「無置換」の意味である。
　一方、用語「置換(substituted)」は、母核となる基のいずれかの水素原子が、母核と同一または異なる構造の基で置換されていることを意味する。従って、「置換基」は、母核となる基に結合した他の基である。置換基は１個であってもよいし、２個以上であってもよい。２個以上の置換基は同一であってもよいし、異なるものであってもよい。 In the present invention, the term "unsubstituted" means only scaffolding groups. When only the name of the base group is used, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that one of the hydrogen atoms in the scaffold group is replaced with a group having the same or different structure as that of the scaffold. Thus, a "substituent" is another group attached to a scaffold group. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
　「置換基」は化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。
　「置換基」となり得る基の具体例としては、以下の基を挙げることができる。
　フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；
　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；
　ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などのＣ２～６アルケニル基；
　エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などのＣ２～６アルキニル基； A "substituent" is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Specific examples of groups that can be "substituents" include the following groups.
Halogeno groups such as fluoro, chloro, bromo and iodo groups;
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group alkyl group;
vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group , 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 -C2-6 alkenyl groups such as hexenyl group and 5-hexenyl group;
ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group , 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc. C2-6 alkynyl group of;
　シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；
　２－シクロプロペニル基、２－シクロペンテニル基、３－シクロヘキセニル基などのＣ３～６シクロアルケニル基；
　フェニル基、ナフチル基などのＣ６～１０アリール基；
　ベンジル基、フェネチル基などのＣ６～１０アリールＣ１～６アルキル基；
　３～６員環のヘテロシクリル基；
　３～６員環のへテロシクリルＣ１～６アルキル基； C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group;
2-cyclopropenyl group, 2-cyclopentenyl group, C3-6 cycloalkenyl group such as 3-cyclohexenyl group;
C6-10 aryl group such as phenyl group and naphthyl group;
C6-10 aryl C1-6 alkyl groups such as benzyl group and phenethyl group;
3- to 6-membered heterocyclyl group;
3- to 6-membered heterocyclyl C1-6 alkyl group;
　水酸基；
　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；
　ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などのＣ２～６アルケニルオキシ基；
　エチニルオキシ基、プロパルギルオキシ基などのＣ２～６アルキニルオキシ基；
　フェノキシ基、ナフトキシ基などのＣ６～１０アリールオキシ基；
　ベンジルオキシ基、フェネチルオキシ基などのＣ６～１０アリールＣ１～６アルコキシ基； hydroxyl group;
C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy and t-butoxy;
C2-6 alkenyloxy groups such as a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group;
C2-6 alkynyloxy groups such as an ethynyloxy group and a propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
C6-10 aryl C1-6 alkoxy groups such as benzyloxy group and phenethyloxy group;
　カルボキシ基；
　ホルミル基；
　アセチル基、プロピオニル基などのＣ１～６アルキルカルボニル基；
　ホルミルオキシ基；
　アセチルオキシ基、プロピオニルオキシ基などのＣ１～６アルキルカルボニルオキシ基；
　メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などのＣ１～６アルコキシカルボニル基； carboxy group;
formyl group;
C1-6 alkylcarbonyl groups such as acetyl group and propionyl group;
formyloxy group;
C1-6 alkylcarbonyloxy groups such as an acetyloxy group and a propionyloxy group;
Methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, C1-6 alkoxycarbonyl group such as t-butoxycarbonyl group;
　クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基、パーフルオロ－ｎ－ペンチル基などのＣ１～６ハロアルキル基；
　２－クロロ－１－プロペニル基、２－フルオロ－１－ブテニル基などのＣ２～６ハロアルケニル基；
　４，４－ジクロロ－１－ブチニル基、４－フルオロ－１－ペンチニル基、５－ブロモ－２－ペンチニル基などのＣ２～６ハロアルキニル基；
　３，３－ジフルオロシクロブチル基などのＣ３～６ハロシクロアルキル基；
　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基、２，２，２－トリフルオロエトキシ基などのＣ１～６ハロアルコキシ基；
　２－クロロプロペニルオキシ基、３－ブロモブテニルオキシ基などのＣ２～６ハロアルケニルオキシ基；
　クロロアセチル基、トリフルオロアセチル基、トリクロロアセチル基などのＣ１～６ハロアルキルカルボニル基； C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group;
C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
C3-6 halocycloalkyl groups such as 3,3-difluorocyclobutyl groups;
C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group and 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group and trichloroacetyl group;
　アミノ基；
　メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのＣ１～６アルキル置換アミノ基；
　アニリノ基、ナフチルアミノ基などのＣ６～１０アリールアミノ基；
　ベンジルアミノ基、フェネチルアミノ基などのＣ６～１０アリールＣ１～６アルキルアミノ基； amino group;
C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group and diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
C6-10 aryl C1-6 alkylamino groups such as benzylamino group and phenethylamino group;
　ホルミルアミノ基；
　アセチルアミノ基、プロピオニルアミノ基、ブチリルアミノ基、ｉ－プロピルカルボニルアミノ基などのＣ１～６アルキルカルボニルアミノ基；
　メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、ｎ－プロポキシカルボニルアミノ基、ｉ－プロポキシカルボニルアミノ基などのＣ１～６アルコキシカルボニルアミノ基；
　カルバモイル基、ジメチルアミノカルボニル基、フェニルアミノカルボニル基、Ｎ－フェニル－Ｎ－メチルアミノカルボニル基などの無置換若しくは置換基を有するアミノカルボニル基；
　イミノメチル基、（１－イミノ）エチル基、（１－イミノ）－ｎ－プロピル基などのイミノＣ１～６アルキル基；
　Ｎ－ヒドロキシ－イミノメチル基、（１－（Ｎ－ヒドロキシ）－イミノ）エチル基、（１－（Ｎ－ヒドロキシ）－イミノ）プロピル基、Ｎ－メトキシ－イミノメチル基、（１－（Ｎ－メトキシ）－イミノ）エチル基などの置換若しくは無置換のＮ－ヒドロキシイミノＣ１～６アルキル基；
　アミノカルボニルオキシ基；
　エチルアミノカルボニルオキシ基、ジメチルアミノカルボニルオキシ基などのＣ１～６アルキル置換アミノカルボニルオキシ基； formylamino group;
C1-6 alkylcarbonylamino groups such as acetylamino group, propionylamino group, butyrylamino group, i-propylcarbonylamino group;
C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group;
unsubstituted or substituted aminocarbonyl group such as carbamoyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N-phenyl-N-methylaminocarbonyl group;
imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, (1-imino)-n-propyl group;
N-hydroxy-iminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N-methoxy-iminomethyl group, (1-(N-methoxy) -imino) substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as ethyl groups;
aminocarbonyloxy group;
C1-6 alkyl-substituted aminocarbonyloxy groups such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;
　メルカプト基；
　メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｉ－プロピルチオ基、ｎ－ブチルチオ基、ｉ－ブチルチオ基、ｓ－ブチルチオ基、ｔ－ブチルチオ基などのＣ１～６アルキルチオ基；
　トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基；
　ビニルチオ基、アリルチオ基などのＣ２～６アルケニルチオ基；
　エチニルチオ基、プロパルギルチオ基などのＣ２～６アルキニルチオ基；
　メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などのＣ１～６アルキルスルフィニル基；
　トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；
　アリルスルフィニル基などのＣ２～６アルケニルスルフィニル基；
　プロパルギルスルフィニル基などのＣ２～６アルキニルスルフィニル基；
　メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などのＣ１～６アルキルスルホニル基；
　トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；
　アリルスルホニル基などのＣ２～６アルケニルスルホニル基；
　プロパルギルスルホニル基などのＣ２～６アルキニルスルホニル基；
　アミノチオカルボニル基；
　Ｓ，Ｓ－ジメチルスルホキシイミノ基などのＣ１～６アルキルスルホキシイミノ基； mercapto group;
C1-6 alkylthio groups such as methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio and t-butylthio;
C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group;
C2-6 alkenylthio groups such as a vinylthio group and an allylthio group;
C2-6 alkynylthio groups such as ethynylthio group and propargylthio group;
C1-6 alkylsulfinyl groups such as a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group;
C2-6 alkenylsulfinyl groups such as allylsulfinyl groups;
C2-6 alkynylsulfinyl groups such as propargylsulfinyl groups;
C1-6 alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group;
C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group;
C2-6 alkenylsulfonyl groups such as allylsulfonyl groups;
C2-6 alkynylsulfonyl groups such as propargylsulfonyl groups;
aminothiocarbonyl group;
C1-6 alkylsulfoxyimino groups such as S,S-dimethylsulfoxyimino groups;
　トリメチルシリル基、トリエチルシリル基、ｔ－ブチルジメチルシリル基などのトリＣ１～６アルキル置換シリル基；
　トリフェニルシリル基などのトリＣ６～１０アリール置換シリル基；
　シアノ基；
　ニトロ基； tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group and t-butyldimethylsilyl group;
tri-C6-10 aryl-substituted silyl groups such as triphenylsilyl groups;
cyano group;
nitro group;
　「Ｃ１～６」などの用語は、母核となる基の炭素原子数が１～６個などであることを表している。この炭素原子数には、置換基の中に在る炭素原子の数を含まない。例えば、エトキシブチル基は、母核となる基がブチル基であり、置換基がエトキシ基であるので、Ｃ２アルコキシＣ４アルキル基に分類する。 A term such as "C1-6" indicates that the number of carbon atoms in the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms in substituent groups. For example, an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the base group is a butyl group and the substituent is an ethoxy group.
　また、上記の「３～６員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１～４個のヘテロ原子を環の構成原子として含む。「３～６員環のヘテロシクリル基」としては、３～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。 In addition, the above-mentioned "3- to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur atoms as ring-constituting atoms. The "3- to 6-membered heterocyclyl group" includes a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
　３～６員環の飽和ヘテロシクリル基としては、アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。 3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, A dioxolanyl group, a dioxanyl group and the like can be mentioned.
　５員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などを挙げることができる。
　６員環のヘテロアリール基としては、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などを挙げることができる。
　５員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などを挙げることができる。
　６員環の部分不飽和ヘテロシクリル基としては、ジヒドロピラニル基などを挙げることができる。
　これらの「置換基」は、当該置換基中のいずれかの水素原子が、異なる構造の基で置換されていてもよい。 Five-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. can be mentioned.
A pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, etc. can be mentioned as a 6-membered heteroaryl group.
Examples of the 5-membered partially unsaturated heterocyclyl group include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, and isoxazolinyl groups.
Examples of the 6-membered partially unsaturated heterocyclyl group include a dihydropyranyl group.
Any hydrogen atom in these "substituents" may be substituted with a group having a different structure.
〔Ｙ１〕
　Ｙ１は、酸素原子または硫黄原子を示す。
　本発明においては、好ましいＹ１は酸素原子である。 [ Y1 ]
Y 1 represents an oxygen atom or a sulfur atom.
In the present invention, Y 1 is preferably an oxygen atom.
〔Ｘ１、Ｘ２およびＸ４〕
　Ｘ１、Ｘ２およびＸ４は、それぞれ独立に、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基、またはＲ１Ｏ－Ｎ＝ＣＲ６－で表される基を示す。 [X 1 , X 2 and X 4 ]
X 1 , X 2 and X 4 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group , a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted A C6-10 arylsulfonyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyl group, a substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a nitro group, a cyano group, represented by R 1 -CO- , a carboxy group, a group represented by R 2 —O—CO—, a group represented by R 3 R 4 N—, a group represented by R 3 R 4 N—CO—, R 1 —CO a group represented by -O-, a group represented by R 1 -CO-NR 5 -, a group represented by R 2 -O-CO-O-, a group represented by R 2 -O-CO-NR 5 - a group represented by R 3 R 4 N—CO—O—, a group represented by R 3 R 4 N—CO—NR 5 —, a group represented by R 2 SO 2 —NR 5 — , a group represented by R 3 R 4 N--SO 2 --, or a group represented by R 1 ON=CR 6 --.
　Ｒ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ２は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ３は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ４は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよい。
　Ｒ５は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒ６は、水素原子、ハロゲノ基、アミノ基、置換若しくは無置換のモノＣ１～６アルキルアミノ基、置換若しくは無置換のジＣ１～６アルキルアミノ基、置換若しくは無置換のＣ１～６アルキル基、置換もしくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。 R 1 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
R 2 is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo It represents an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
R 3 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Each R 4 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Here, R 3 and R 4 may together form a divalent organic group.
Each R 5 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
R 6 is a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, It represents a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
　Ｘ１、Ｘ２およびＸ４における「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。 Examples of the “halogeno group” for X 1 , X 2 and X 4 include a fluoro group, a chloro group, a bromo group and an iodo group.
　Ｘ１、Ｘ２およびＸ４における「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。Ｘ１における「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。 The “C1-6 alkyl group” for X 1 , X 2 and X 4 may be linear or branched. The "C1-6 alkyl group" for X 1 includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などを挙げることができる。 The "C2-6 alkenyl group" for X 1 , X 2 and X 4 includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl -2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2- butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などを挙げることができる。 The "C2-6 alkynyl group" for X 1 , X 2 and X 4 includes an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl -2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3- Pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like can be mentioned.
　Ｘ１、Ｘ２およびＸ４における「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、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、ｉ－ヘキシルオキシ基などを挙げることができる。
　Ｘ１、Ｘ２およびＸ４における「Ｃ２～６アルケニルオキシ基」としては、ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などを挙げることができる。
　Ｘ１、Ｘ２およびＸ４における「Ｃ２～６アルキニルオキシ基」としては、エチニルオキシ基、プロパルギルオキシ基などを挙げることができる。 The "C1-6 alkoxy group" for X 1 , X 2 and X 4 includes methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of the “C2-6 alkenyloxy group” for X 1 , X 2 and X 4 include vinyloxy, allyloxy, propenyloxy, butenyloxy and the like.
Examples of the "C2-6 alkynyloxy group" for X 1 , X 2 and X 4 include an ethynyloxy group and a propargyloxy group.
　Ｘ１、Ｘ２およびＸ４における「Ｃ１～６アルキルチオ基」としては、メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｎ－ブチルチオ基、ｎ－ペンチルチオ基、ｎ－ヘキシルチオ基、ｉ－プロピルチオ基などを挙げることができる。
　Ｘ１、Ｘ２およびＸ４における「Ｃ１～６アルキルスルフィニル基」としては、メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などを挙げることができる。
　Ｘ１、Ｘ２およびＸ４における「Ｃ１～６アルキルスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などを挙げることができる。 The "C1-6 alkylthio group" for X 1 , X 2 and X 4 includes methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, i-propylthio and the like. can be mentioned.
Examples of the "C1-6 alkylsulfinyl group" for X 1 , X 2 and X 4 include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
Examples of the “C1-6 alkylsulfonyl group” for X 1 , X 2 and X 4 include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」、「Ｃ１～６アルコキシ基」、「Ｃ２～６アルケニルオキシ基」、「Ｃ２～６アルキニルオキシ基」、「Ｃ１～６アルキルチオ基」、「Ｃ１～６アルキルスルフィニル基」、または「Ｃ１～６アルキルスルホニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；（エチリデンアミノ）オキシ基、プロパン－２－イリデンアミノ）オキシ基などの（Ｃ１～６アルキリデンアミノ）オキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；またはシアノ基が好ましい。 "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group" for X 1 , X 2 and X 4 , Substituents on the "C2-6 alkynyloxy group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group" or "C1-6 alkylsulfonyl group" include a fluoro group, a chloro group and a bromo group , a halogeno group such as an iodine group; a hydroxyl group; Alkoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1-6 haloalkoxy group such as trifluoromethoxy group; (ethylideneamino)oxy group, propane-2-ylideneamino)oxy group and the like (C1-6 alkylideneamino) oxy group; cyclopropyl group, cyclobutyl group, cyclopentyl group, C3-6 cycloalkyl group such as cyclohexyl group; phenyl group, C6-10 aryl group such as naphthyl group; 4-methylphenyl group, C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups such as 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, or a C6-10 aryl group substituted with one or more substituents of any one of C1-6 haloalkoxy groups; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl 5-membered ring heteroaryl group such as group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group A 5-membered heteroaryl group substituted with one or more substituents; a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a 6-membered heteroaryl group such as a triazinyl group; a C1-6 alkyl group, A 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a cyano group is preferred.
　Ｘ１、Ｘ２およびＸ４における「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｘ１、Ｘ２およびＸ４における「Ｃ３～６シクロアルキルオキシ基」としては、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などを挙げることができる。 Examples of the “C3-6 cycloalkyl group” for X 1 , X 2 and X 4 include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.
Examples of the "C3-6 cycloalkyloxy group" for X 1 , X 2 and X 4 include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インダニル基、インデニル基、テトラリニル基、などを挙げることができる。
　Ｘ１、Ｘ２およびＸ４における「Ｃ６～１０アリールオキシ基」としては、フェノキシ基、ナフトキシ基などを挙げることができる。 Examples of the “C6-10 aryl group” for X 1 , X 2 and X 4 include phenyl group, naphthyl group, indanyl group, indenyl group, tetralinyl group and the like.
Examples of the “C6-10 aryloxy group” for X 1 , X 2 and X 4 include a phenoxy group and a naphthoxy group.
　Ｘ１、Ｘ２およびＸ４における「Ｃ６～１０アリールチオ基」としては、フェニルチオ基、ナフチルチオ基などを挙げることができる。
　Ｘ１、Ｘ２およびＸ４における「Ｃ６～１０アリールスルフィニル基」としては、フェニルスルフィニル基、ナフチルスルフィニル基などを挙げることができる。
　Ｘ１、Ｘ２およびＸ４における「Ｃ６～１０アリールスルホニル基」としては、フェニルスルホニル基、ナフチルスルホニル基などを挙げることができる。 Examples of the “C6-10 arylthio group” for X 1 , X 2 and X 4 include a phenylthio group and a naphthylthio group.
Examples of the “C6-10 arylsulfinyl group” for X 1 , X 2 and X 4 include a phenylsulfinyl group and a naphthylsulfinyl group.
Examples of the “C6-10 arylsulfonyl group” for X 1 , X 2 and X 4 include a phenylsulfonyl group and a naphthylsulfonyl group.
　Ｘ１、Ｘ２およびＸ４における「５～６員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１、２、３または４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。「５～６員環のヘテロシクリル基」としては、５～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。 The “5- to 6-membered heterocyclyl group” for X 1 , X 2 and X 4 means that 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom are added to the ring. It is a group containing as a constituent atom. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- to 6-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
　５～６員環の飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～６員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基を挙げることができる。
　５～６員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基を挙げることができる。 Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.
　Ｘ１、Ｘ２およびＸ４における「５～６員環のヘテロシクリルオキシ基」は、５～６員環のヘテロシクリル基とオキシ基が結合した構造を有する。具体例としては、チアゾリルオキシ基、ピリジルオキシ基などを挙げることができる。 The “5- to 6-membered heterocyclyloxy group” for X 1 , X 2 and X 4 has a structure in which a 5- to 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.
　Ｘ１、Ｘ２およびＸ４における「Ｃ３～６シクロアルキル基」、「Ｃ３～６シクロアルキルオキシ基」、「Ｃ６～１０アリール基」、「Ｃ６～１０アリールオキシ基」、「Ｃ６～１０アリールチオ基」、「Ｃ６～１０アリールスルフィニル基」、「Ｃ６～１０アリールスルホニル基」、「５～６員環のヘテロシクリル基」、または「５～６員環のヘテロシクリルオキシ基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；またはシアノ基が好ましい。
　さらに、「Ｃ３～６シクロアルキル基」、「Ｃ３～６シクロアルキルオキシ基」、「５～６員環のヘテロシクリル基」、または「５～６員環のヘテロシクリルオキシ基」上の置換基としては、オキソ基も好ましい。 “C3-6 cycloalkyl group”, “C3-6 cycloalkyloxy group”, “C6-10 aryl group”, “C6-10 aryloxy group”, “C6-10 arylthio” for X 1 , X 2 and X 4 group", "C6-10 arylsulfinyl group", "C6-10 arylsulfonyl group", "5- to 6-membered heterocyclyl group", or "5- to 6-membered heterocyclyloxy group" as substituents on , fluoro group, chloro group, bromo group, halogeno group such as iodine group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t- C1-6 alkyl groups such as butyl group, n-pentyl group, n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl C1 ~ 6 haloalkyl groups such as groups; hydroxyl group; C1 ~ 6 alkoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1-6 haloalkoxy group such as trifluoromethoxy group; phenyl group, C6-10 aryl group such as naphthyl group; 4-methyl phenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc., C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl group substituted with one or more substituents selected from haloalkyl group or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl 5-membered ring heteroaryl group such as group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 5-membered heteroaryl group substituted with any one or more substituents of haloalkoxy group; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; C1-6 substituted with one or more substituents selected from an alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group a 6-membered heteroaryl group; or a cyano group.
Furthermore, as a substituent on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "5- to 6-membered heterocyclyl group", or "5- to 6-membered heterocyclyloxy group" , oxo groups are also preferred.
　Ｘ１、Ｘ２およびＸ４における「Ｒ１－ＣＯ－で表される基」中、Ｒ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。 In the “group represented by R 1 —CO—” for X 1 , X 2 and X 4 , R 1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group indicate.
　Ｒ１における「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。
　Ｒ１における「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基などを挙げることができる。
　Ｒ１における「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基などを挙げることができる。
　Ｒ１における「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、または「Ｃ２～６アルキニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；またはシアノ基が好ましい。 The "C1-6 alkyl group" for R 1 includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Examples of the “C2-6 alkenyl group” for R 1 include a vinyl group and a 1-propenyl group.
Examples of the “C2-6 alkynyl group” for R 1 include an ethynyl group and a 1-propynyl group.
Examples of substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in R 1 include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, t-butoxy; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phenyl group, naphthyl C6-10 aryl groups such as groups; C1-6 alkyl groups such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, C6-10 aryl group substituted with one or more substituents selected from C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl 5-membered ring heteroaryl groups such as groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, tetrazolyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno 5-membered heteroaryl group substituted with one or more substituents selected from group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. 6-membered ring heteroaryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents 6 A membered ring heteroaryl group; or a cyano group is preferred.
　Ｒ１における「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｒ１における「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インデニル基、インダニル基、テトラリニル基などを挙げることができる。 Examples of the “C3-6 cycloalkyl group” for R 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the “C6-10 aryl group” for R 1 include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.
　Ｒ１における「５～６員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１、２、３または４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。「５～６員環のヘテロシクリル基」としては、５～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。
　５～６員環の飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～６員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基を挙げることができる。
　５～６員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基が挙げられる。 The “5- to 6-membered heterocyclyl group” for R 1 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- to 6-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro A 6-membered partially unsaturated heterocyclyl group such as a pyranyl group can be mentioned.
　Ｒ１における「Ｃ３～６シクロアルキル基」、「Ｃ６～１０アリール基」、または「５～６員環のヘテロシクリル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；またはシアノ基が好ましい。
　さらに、「Ｃ３～６シクロアルキル基」、または「５～６員環のヘテロシクリル基」上の置換基としては、オキソ基も好ましい。 Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- to 6-membered heterocyclyl group" for R 1 include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. C1 ~ 6 alkyl group of; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, C1 ~ 6 haloalkyl group such as 1-fluoro-n-butyl group; hydroxyl group; methoxy group , ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy groups such as t-butoxy group; 2-chloro-n-propoxy group, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group and 4-chlorophenyl group , 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc., a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group C6-10 aryl group substituted with one or more substituents; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group , a 5-membered heteroaryl group such as a tetrazolyl group; substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group 5-membered heteroaryl group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered heteroaryl group such as triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 A 6-membered heteroaryl group substituted with one or more substituents selected from ∼6 haloalkyl groups or C1-6 haloalkoxy groups; or a cyano group is preferable.
Furthermore, an oxo group is also preferred as a substituent on the "C3-6 cycloalkyl group" or the "5- to 6-membered heterocyclyl group".
　「Ｒ１－ＣＯ－で表される基」の具体例としては、ホルミル基、アセチル基、プロピオニル基、ブチリル基、ｉ－プロピルカルボニル基などを挙げることができる。 Specific examples of the "group represented by R 1 -CO-" include formyl, acetyl, propionyl, butyryl, i-propylcarbonyl and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｒ２－Ｏ－ＣＯ－で表される基」中、Ｒ２は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ２における置換基の具体例は、Ｒ１において例示したものと同じものを挙げることができる。 In the "group represented by R -O - CO-" for X 1 , X 2 and X 4 , R 2 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group , a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group show.
Specific examples of substituents for R 2 are the same as those exemplified for R 1 .
　「Ｒ２－Ｏ－ＣＯ－で表される基」の具体例としては、メトキシカルボニル基、エトキシカルボニル基、ｔ－ブトキシカルボニル基などを挙げることができる。 Specific examples of the “group represented by R 2 —O—CO—” include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｒ３Ｒ４Ｎ－で表される基」中、Ｒ３は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、Ｒ４は、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒ３またはＲ４における置換基の具体例は、Ｒ１において例示したものと同じものを挙げることができる。 In the "group represented by R 3 R 4 N-" for X 1 , X 2 and X 4 , R 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl R 4 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of substituents for R 3 or R 4 are the same as those exemplified for R 1 .
　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよい。
　形成できる二価の有機基としては、置換若しくは無置換のＣ２～５アルキレン基または置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ２～５アルキレン基」としては、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ２～５アルキレン基」または「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；またはクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。 Here, R 3 and R 4 may together form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
　「Ｒ３Ｒ４Ｎ－で表される基」の具体例としては、アミノ基、メチルアミノ基、ジメチルアミノ基、ｉ－プロピルアミノ基などを挙げることができる。 Specific examples of the “group represented by R 3 R 4 N—” include amino group, methylamino group, dimethylamino group, i-propylamino group and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｒ３Ｒ４Ｎ－ＣＯ－で表される基」中、Ｒ３およびＲ４は上記の「Ｒ３Ｒ４Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ３Ｒ４Ｎ－ＣＯ－で表される基」の具体例としては、カルバモイル基、Ｎ，Ｎ－ジメチルアミノカルボニル基、Ｎ－（ｉ－プロピル）アミノカルボニル基、Ｎ－（ｉ－プロピル）－Ｎ－メチルアミノカルボニル基などを挙げることができる。 In the “group represented by R 3 R 4 N—CO—” for X 1 , X 2 and X 4 , R 3 and R 4 are the same as those in the above “group represented by R 3 R 4 N—” have similar meanings.
Specific examples of the “group represented by R 3 R 4 N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, an N-(i-propyl )—N-methylaminocarbonyl group and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｒ１－ＣＯ－Ｏ－で表される基」中、Ｒ１は上記の「Ｒ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒ１－ＣＯ－Ｏ－で表される基」の具体例としては、アセチルオキシ基、ｉ－プロピルカルボニルオキシ基などを挙げることができる。 In the "group represented by R 1 -CO-O-" for X 1 , X 2 and X 4 , R 1 has the same meaning as the above "group represented by R 1 -CO-".
Specific examples of the "group represented by R 1 -CO-O-" include an acetyloxy group and an i-propylcarbonyloxy group.
　Ｘ１、Ｘ２およびＸ４における「Ｒ１－ＣＯ－ＮＲ５－で表される基」中、Ｒ１は上記の「Ｒ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　Ｒ５は、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒ５における置換基の具体例は、Ｒ１において例示したものと同じものを挙げることができる。
　「Ｒ１－ＣＯ－ＮＲ５－で表される基」の具体例としては、アセチルアミノ基、ｉ－プロピルカルボニルアミノ基などを挙げることができる。 In the "group represented by R 1 -CO-NR 5 -" for X 1 , X 2 and X 4 , R 1 has the same meaning as in the above "group represented by R 1 -CO-". .
R 5 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of substituents for R 5 are the same as those exemplified for R 1 .
Specific examples of the "group represented by R 1 -CO-NR 5 -" include an acetylamino group and an i-propylcarbonylamino group.
　Ｘ１、Ｘ２およびＸ４における「Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基」中、Ｒ２は上記の「Ｒ２－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基」の具体例としては、メトキシカルボニルオキシ基、エトキシカルボニルオキシ基などを挙げることができる。 In the “group represented by R 2 —O—CO—O—” for X 1 , X 2 and X 4 , R 2 is the same as the above “group represented by R 2 —O—CO—” indicate meaning.
Specific examples of the “group represented by R 2 —O—CO—O—” include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.
　Ｘ１、Ｘ２およびＸ４における「Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基」中、Ｒ２は上記の「Ｒ２－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒ５は上記の「Ｒ１－ＣＯ－ＮＲ５－で表される基」におけるそれと同様の意味を示す。
　「Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基」の具体例としては、メトキシカルボニルアミノ基などを挙げることができる。 In the "group represented by R 2 -O-CO-NR 5 -" for X 1 , X 2 and X 4 , R 2 is the same as in the above "group represented by R 2 -O-CO-" indicates the meaning of R 5 has the same meaning as in the above “group represented by R 1 —CO—NR 5 —”.
Specific examples of the “group represented by R 2 —O—CO—NR 5 —” include a methoxycarbonylamino group.
　Ｘ１、Ｘ２およびＸ４における「Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基」中、Ｒ３およびＲ４は上記の「Ｒ３Ｒ４Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基」の具体例としては、カルバモイルオキシ基、Ｎ，Ｎ－ジメチルアミノカルボニルオキシ基などを挙げることができる。 In the “group represented by R 3 R 4 N—CO—O—” for X 1 , X 2 and X 4 , R 3 and R 4 are the above “group represented by R 3 R 4 N—” have similar meanings.
Specific examples of the “group represented by R 3 R 4 N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.
　Ｘ１、Ｘ２およびＸ４における「Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基」中、Ｒ３およびＲ４は上記の「Ｒ３Ｒ４Ｎ－で表される基」におけるそれらと同様の意味を示す。Ｒ５は上記の「Ｒ１－ＣＯ－ＮＲ５－で表される基」におけるそれと同様の意味を示す。
　「Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基」の具体例としては、カルバモイルアミノ基、Ｎ，Ｎ－ジメチルアミノカルボニルアミノ基などを挙げることができる。 In the “group represented by R 3 R 4 N—CO—NR 5 —” for X 1 , X 2 and X 4 , R 3 and R 4 are the above “group represented by R 3 R 4 N—” have similar meanings to those in R 5 has the same meaning as in the above “group represented by R 1 —CO—NR 5 —”.
Specific examples of the “group represented by R 3 R 4 N—CO—NR 5 —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.
　Ｘ１、Ｘ２およびＸ４における「Ｒ２ＳＯ２－ＮＲ５－で表される基」中、Ｒ２は上記の「Ｒ２－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒ５は上記の「Ｒ１－ＣＯ－ＮＲ５－で表される基」におけるそれと同様の意味を示す。
　「Ｒ２ＳＯ２－ＮＲ５－で表される基」の具体例としては、メタンスルホニルアミノ基などを挙げることができる。 In the "group represented by R 2 SO 2 -NR 5 -" for X 1 , X 2 and X 4 , R 2 has the same meaning as in the above "group represented by R 2 -O-CO-". indicates R 5 has the same meaning as in the above “group represented by R 1 —CO—NR 5 —”.
Specific examples of the “group represented by R 2 SO 2 —NR 5 —” include a methanesulfonylamino group and the like.
　Ｘ１、Ｘ２およびＸ４における「Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基」中、Ｒ３およびＲ４は上記の「Ｒ３Ｒ４Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基」の具体例としては、Ｎ，Ｎ－ジメチルアミノスルホニル基などを挙げることができる。 In the “group represented by R 3 R 4 N—SO 2 —” for X 1 , X 2 and X 4 , R 3 and R 4 are those in the above “group represented by R 3 R 4 N—” has the same meaning as
Specific examples of the “group represented by R 3 R 4 N—SO 2 —” include an N,N-dimethylaminosulfonyl group.
　Ｘ１、Ｘ２およびＸ４における「Ｒ１Ｏ－Ｎ＝ＣＲ６－で表される基」中、Ｒ１は上記の「Ｒ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　Ｒ６は、水素原子、ハロゲノ基、アミノ基、置換若しくは無置換のモノＣ１～６アルキルアミノ基、置換若しくは無置換のジＣ１～６アルキルアミノ基、置換若しくは無置換のＣ１～６アルキル基、置換もしくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ６における「置換若しくは無置換のＣ１～６アルキル基」または「置換若しくは無置換の５～６員環のヘテロシクリル基」の具体例は、Ｒ１において例示したものと同じものを挙げることができる。
　Ｒ６における「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。
　Ｒ６における「置換若しくは無置換のモノＣ１～６アルキルアミノ基」の「モノＣ１～６アルキルアミノ基」としては、メチルアミノ基、エチルアミノ基、ｉ－プロピルアミノ基などを挙げることができる。
　Ｒ６における「置換若しくは無置換のジＣ１～６アルキルアミノ基」の「ジＣ１～６アルキルアミノ基」としては、ジメチルアミノ基、ジエチルアミノ基、Ｎ－メチル－Ｎ－ｉ－プロピルアミノ基などを挙げることができる。
　Ｒ６における「置換もしくは無置換のＣ１～６アルコキシ基」の「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、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、ｉ－ヘキシルオキシ基などを挙げることができる。
　Ｒ６における「置換若しくは無置換のＣ１～６アルキルチオ基」の「Ｃ１～６アルキルチオ基」としては、メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｎ－ブチルチオ基、ｎ－ペンチルチオ基、ｎ－ヘキシルチオ基、ｉ－プロピルチオ基などを挙げることができる。
　Ｒ６における「Ｃ１～６アルコキシ基」、「モノＣ１～６アルキルアミノ基」、「ジＣ１～６アルキルアミノ基」、または「Ｃ１～６アルキルチオ基」上の置換基としては、Ｒ１において「Ｃ１～６アルキル基」上の置換基として例示した置換基と同じものを挙げることができる。
　「Ｒ１Ｏ－Ｎ＝ＣＲ６－で表される基」の具体例としては、（ヒドロキシイミノ）メチル基、（エトキシイミノ）メチル基、１－（ｉ－プロポキシイミノ）エチル基などを挙げることができる。 In the "group represented by R1ON = CR6- " for X1, X2 and X4, R1 has the same meaning as in the above "group represented by R1 - CO- ". show.
R 6 is a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, It represents a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Specific examples of the "substituted or unsubstituted C1-6 alkyl group" or "substituted or unsubstituted 5- to 6-membered heterocyclyl group" for R 6 are the same as those exemplified for R 1 . .
Examples of the “halogeno group” for R 6 include a fluoro group, a chloro group, a bromo group and an iodo group.
Examples of the “mono C1-6 alkylamino group” of the “substituted or unsubstituted mono C1-6 alkylamino group” for R 6 include a methylamino group, an ethylamino group and an i-propylamino group.
Examples of the "di-C1-6 alkylamino group" of the "substituted or unsubstituted di-C1-6 alkylamino group" for R 6 include a dimethylamino group, a diethylamino group, an N-methyl-Ni-propylamino group, and the like. can be mentioned.
The "C1-6 alkoxy group" of the "substituted or unsubstituted C1-6 alkoxy group" for R 6 includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, n- A hexyloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group and the like can be mentioned.
The "C1-6 alkylthio group" of the "substituted or unsubstituted C1-6 alkylthio group" for R 6 includes methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio groups, i-propylthio groups, and the like.
Substituents on the "C1-6 alkoxy group", "mono-C1-6 alkylamino group", "di - C1-6 alkylamino group" or "C1-6 alkylthio group" for R 6 include " The same substituents as exemplified as substituents on "C1-6 alkyl group" can be mentioned.
Specific examples of the “group represented by R 1 ON=CR 6 —” include (hydroxyimino)methyl group, (ethoxyimino)methyl group, 1-(i-propoxyimino)ethyl group, and the like. can be done.
　本発明においては、好ましいＸ１、およびＸ４としては、水素原子または置換若しくは無置換のＣ１～６アルキル基を挙げることができる。Ｘ１、およびＸ４としては、水素原子がさらに好ましい。
　本発明においては、好ましいＸ２としては、「Ｒ１Ｏ－Ｎ＝ＣＲ６－で表される基」を挙げることができる。 In the present invention, preferred X 1 and X 4 are a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. X 1 and X 4 are more preferably hydrogen atoms.
In the present invention, X 2 is preferably "a group represented by R 1 ON=CR 6 -".
　〔Ｑ〕
　Ｑは、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～１０員環のヘテロシクリル基を示す。 [Q]
Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group.
　Ｑにおける「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インデニル基、インダニル基、テトラリニル基などを挙げることができる。 Examples of the "C6-10 aryl group" for Q include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group, and the like.
　Ｑにおける「５～１０員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１、２、３または４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。単環および多環のいずれでもよい。
　「５～１０員環のヘテロシクリル基」としては、５～６員環の飽和ヘテロシクリル基、５～１０員環のヘテロアリール基、５～１０員環の部分不飽和ヘテロシクリル基などを挙げることができる。 The “5- to 10-membered heterocyclyl group” for Q is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur atoms as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic.
Examples of the "5- to 10-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .
　５～６員環の飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～１０員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；インドリル基、イソインドリル基、ベンゾフラニル基、ベンゾチエニル基、インダゾリル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾイソオキサオゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基などの９員ヘテロアリール基；キノリニル基、イソキノリニル基、シンノリニル基、フタラジニル基、キナゾリニル基、キノキサリニル基などの１０員ヘテロアリール基；を挙げることができる。
　５～１０員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基；インドリニル基、イソインドリニル基、２，３－ジヒドロベンゾフラニル基、１，３－ジヒドロベンゾフラニル基などの９員環の部分不飽和ヘテロシクリル基；１，２，３，４－テトラヒドロキノリニル基などの１０員環の部分不飽和ヘテロシクリル基；を挙げることができる。 Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc. 10-membered heteroaryl group;
Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl group; 9-membered partially unsaturated ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;
　Ｑにおける「Ｃ６～１０アリール基」または「５～１０員環のへテロシクリル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；ビニル基などのＣ２～６アルケニル基；エチニル基などのＣ２～６アルキニル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；メトキシメチル基などのＣ１～６アルコキシＣ１～６アルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；ヒドロキシエトキシ基などのヒドロキシＣ１～６アルコキシ基；メトキシメトキシ基、メトキシエトキシ基などのＣ１～６アルコキシアルコキシ基；トリメチルシリルオキシエトキシ基、ｔ－ブチルジメチルシリルオキシエトキシ基などのトリＣ１～６アルキル置換シリルオキシＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；Ｃ３～６シクロアルキルＣ１～６アルコキシ基；Ｃ６～１０アリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルコキシ基；５員環のヘテロアリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール）Ｃ１～６アルコキシ基；６員環のヘテロアリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール）Ｃ１～６アルコキシ基；メチルチオ基、エチルチオ基などのＣ１～６アルキルチオ基：メチルスルフィニル基、エチルスルフィニル基などのＣ１～６アルキルスルフィニル基；メチルスルホニル基、エチルスルホニル基などのＣ１～６アルキルスルホニル基；トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基：トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；シクロプロピル基、シクロブチル基、シクロペンチル基などのＣ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、またはシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；シクロプロぺニル基、シクロブテニル基、シクロペンテニル基などのＣ３～６シクロアルケニル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－フルオロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基などの３～４員環の飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された３～４員環の飽和ヘテロシクリル基；ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などの５～６員環の飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環の飽和ヘテロシクリル基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基でのいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和へテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環の部分飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環の部分飽和ヘテロシクリル基； 
ＲＱ１－ＣＯ－で表される基　（式中、ＲＱ１は、水素原子；Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；Ｃ２～６アルケニル基；Ｃ２～６ハロアルケニル基；Ｃ２～６アルキニル基；Ｃ２～６ハロアルキニル基；Ｃ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、若しくはシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；Ｃ６～１０アリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；５～６員環のヘテロアリール基；または；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール基；を示す。以下のＲＱ１においても同じ。）；
カルボキシ基；
ＲＱ２－Ｏ－ＣＯ－で表される基　（式中、ＲＱ２は、Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；Ｃ２～６アルケニル基；Ｃ２～６ハロアルケニル基；Ｃ２～６アルキニル基；Ｃ２～６ハロアルキニル基；Ｃ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、若しくはシアノ基で置換されたＣ３～６シクロアルキル基；Ｃ６～１０アリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；５～６員環のヘテロアリール基；または；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール基；を示す。以下のＲＱ２においても同じ。）；
ＲＱ１ＲＱ１Ｎ－で表される基（式中のＲＱ１は同一でも異なっていてもよい。ＲＱ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ＲＱ１ＲＱ１Ｎ－ＣＯ－で表される基（式中のＲＱ１は同一でも異なっていてもよい。ＲＱ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ＲＱ１－ＣＯ－Ｏ－で表される基；ＲＱ１－ＣＯ－ＮＲＱ３－で表される基（式中、ＲＱ３は、水素原子；Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；または（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；を示す。以下のＲＱ３においても同じ。）；
ＲＱ２－Ｏ－ＣＯ－Ｏ－で表される基；ＲＱ２－Ｏ－ＣＯ－ＮＲＱ３－で表される基；ＲＱ１ＲＱ１Ｎ－ＣＯ－Ｏ－で表される基（式中のＲＱ１は同一でも異なっていてもよい。ＲＱ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ＲＱ１ＲＱ１Ｎ－ＣＯ－ＮＲＱ３－で表される基（式中のＲＱ１は同一でも異なっていてもよい。ＲＱ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；ＲＱ２ＳＯ２－ＮＲＱ３－で表される基；ＲＱ１ＲＱ１Ｎ－ＳＯ２－で表される基（式中のＲＱ１は同一でも異なっていてもよい。ＲＱ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ＲＱ１－Ｏ－Ｎ＝Ｃ（ＲＱ４）－で表される基（式中、ＲＱ４は、水素原子またはＣ１～６アルキル基を示す。）；（ＲＱ１）２Ｃ＝Ｎ－Ｏ－で表される基（式中のＲＱ１は同一でも異なっていてもよい。ＲＱ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
　ペンタフルオロスルファニル基、トリメチルシリルエチニル基、ニトロ基、またはシアノ基が好ましい。
　さらに、「５～１０員環のヘテロシクリル基」上の置換基としては、オキソ基も好ましい。 Examples of substituents on the "C6-10 aryl group" or "5- to 10-membered heterocyclyl group" in Q include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; a methyl group, an ethyl group, C1-6 alkyl groups such as n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; vinyl group, etc. C2-6 alkenyl group of; C2-6 alkynyl group such as ethynyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group and the like C1-6 haloalkyl group; C1-6 alkoxy C1-6 alkyl group such as methoxymethyl group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i C1-6 alkoxy groups such as -butoxy group and t-butoxy group; hydroxy C1-6 alkoxy groups such as hydroxyethoxy group; C1-6 alkoxyalkoxy groups such as methoxymethoxy group and methoxyethoxy group; trimethylsilyloxyethoxy group, t -Tri-C1-6 alkyl-substituted silyloxy C1-6 alkoxy groups such as butyldimethylsilyloxyethoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10 aryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 halo C6-10 aryl substituted with any one or more substituents of an alkoxy group)C1-6 alkoxy group; 5-membered ring heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, 5-membered heteroaryl)C1-6 alkoxy group; 6-membered heteroaryl C1-6 substituted with one or more substituents selected from a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group Alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) 6-membered heteroaryl substituted with one or more substituents ) C1-6 alkoxy group; C1-6 alkylthio group such as methylthio group and ethylthio group; C1-6 alkyl group such as methylsulfinyl group and ethylsulfinyl group sulfinyl group; methylsulfonyl group, C1-6 alkylsulfonyl group such as ethylsulfonyl group; trifluoromethylthio group, C1-6 haloalkylthio group such as 2,2,2-trifluoroethylthio group: trifluoromethylsulfinyl group, C1-6 haloalkylsulfinyl groups such as 2,2,2-trifluoroethylsulfinyl group; trifluoromethylsulfonyl group, C1-6 haloalkylsulfonyl groups such as 2,2,2-trifluoroethylsulfonyl group; cyclopropyl group, C3-6 cycloalkyl group such as cyclobutyl group and cyclopentyl group; any one or more of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or cyano group C3 ~ 6 cycloalkyl group substituted with a substituent of; cyclopropenyl group, cyclobutenyl group, C3 ~ 6 cycloalkenyl group such as cyclopentenyl group; phenyl group, C6 ~ 10 aryl group such as naphthyl group; 4-methyl C1-6 alkyl groups, C1-6 alkoxy groups such as phenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, C6-10 aryl group substituted with one or more substituents selected from halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; 3-4 groups such as aziridinyl group, epoxy group, azetidinyl group and oxetanyl group saturated membered heterocyclyl group; 3-4 substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5- to 6-membered saturated heterocyclyl groups such as a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group; A 5- to 6-membered saturated heterocyclyl group substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl 5-membered ring heteroaryl group such as group, tetrazolyl group; any one or more substituents in C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5-membered heteroaryl group substituted with; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered heteroaryl group such as triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a C1-6 haloalkyl group, or a 6-membered heteroaryl group substituted with one or more substituents of a C1-6 haloalkoxy group; pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group , 5-membered partially unsaturated heterocyclyl group such as isoxazolinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5-membered partially saturated heterocyclyl group substituted with one or more substituents; 6-membered partially unsaturated heterocyclyl group such as dihydropyranyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 ~6 haloalkyl group, or a 6-membered partially saturated heterocyclyl group substituted with one or more substituents of a C1~6 haloalkoxy group;
A group represented by R Q1 —CO— (wherein R Q1 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, C1-6 alkyl group substituted with one or more substituents of a phenyl group or a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a haloalkyl group or a C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from ∼6 haloalkyl group or C1-6 haloalkoxy group)C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or a C3-6 cycloalkyl group substituted with one or more substituents of a cyano group; a C6-10 aryl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or C6-10 aryl group substituted with one or more substituents of any one of C1-6 haloalkoxy groups; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, a 5- to 6-membered heteroaryl group substituted with one or more substituents; The same applies to R Q1 below.);
carboxy group;
A group represented by R Q2 —O—CO— (wherein R Q2 is a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl or a C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl C6-10 aryl)C1-6 alkyl group substituted with one or more substituents, or C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from a 6-haloalkyl group or a C1-6 haloalkoxy group) C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl group C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or C3-6 cycloalkyl group substituted with cyano group; C6-10 aryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group a C6-10 aryl group substituted with one or more substituents; a 5- to 6-membered heteroaryl group; or; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1 A 5- to 6-membered heteroaryl group substituted with one or more substituents selected from ∼6 haloalkoxy groups;
A group represented by R Q1 R Q1 N— (R Q1 in the formula may be the same or different. Together, R Q1 may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.);
A group represented by R Q1 R Q1 N—CO— (in the formula, R Q1 may be the same or different. R Q1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a A methyleneoxydimethylene group may be formed.);
a group represented by R Q1 -CO-O-; a group represented by R Q1 -CO-NR Q3 - (wherein R Q3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; The same applies to R Q3 below.);
a group represented by R Q2 -O-CO-O-; a group represented by R Q2 -O-CO-NR Q3 -; a group represented by R Q1 R Q1 N-CO-O- (in the formula R Q1 may be the same or different, and R Q1 may together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.);
A group represented by R Q1 R Q1 N—CO—NR Q3 — (R Q1 in the formula may be the same or different. Together, R Q1 may be a trimethylene group, a tetramethylene group, a pentamethylene group, , or may form a dimethyleneoxydimethylene group); a group represented by R Q2 SO 2 —NR Q3 —; a group represented by R Q1 R Q1 N—SO 2 — (in the formula, R Q1 may be the same or different, and R Q1 may together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.);
a group represented by R Q1 -ON=C(R Q4 )- (wherein R Q4 represents a hydrogen atom or a C1-6 alkyl group); (R Q1 ) 2 C=N-O- (R Q1 in the formula may be the same or different. R Q1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.);
A pentafluorosulfanyl group, a trimethylsilylethynyl group, a nitro group, or a cyano group are preferred.
Furthermore, an oxo group is also preferred as a substituent on the "5- to 10-membered heterocyclyl group".
　〔Ｘ３〕
　Ｘ３は、水素原子、ハロゲノ基、置換若しくは無置換の直鎖Ｃ１～６アルキル基、置換若しくは無置換の直鎖Ｃ２～６アルケニル基、置換若しくは無置換の直鎖Ｃ２～６アルキニル基、Ｒ１－ＣＯ－で表される基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の４～６員環のヘテロシクリル基を示す。 [ X3 ]
X 3 is a hydrogen atom, a halogeno group, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R A group represented by 1 -CO-, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 4- to 6-membered heterocyclyl group.
　Ｘ３における「直鎖Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基を挙げることができる。
　Ｘ３における「直鎖Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－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－ヘキセニル基を挙げることができる。
　Ｘ３における「直鎖Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－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－ヘキシニル基などを挙げることができる。
　Ｘ３における「４員環のヘテロシクリル基」しては、アゼチジニル基、オキセタニル基を挙げることができる。
　Ｘ３におけるその他の置換基の具体例は、Ｘ１、Ｘ２およびＸ４において例示したものと同じものを挙げることができる。 Examples of the “linear C1-6 alkyl group” for X 3 include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group.
The "linear C2-6 alkenyl group" for X 3 includes a vinyl group, 1-propenyl group, 2-propenyl 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 and 5-hexenyl group can be mentioned.
The "straight-chain C2-6 alkynyl group" for X 3 includes an ethynyl group, 1-propynyl group, 2-propynyl 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 and the like can be mentioned.
Examples of the “4-membered heterocyclyl group” for X 3 include an azetidinyl group and an oxetanyl group.
Specific examples of other substituents for X 3 are the same as those exemplified for X 1 , X 2 and X 4 .
　本発明において、好ましいＸ３としては、置換若しくは無置換の直鎖Ｃ１～６アルキル基、置換若しくは無置換のＣ３～６シクロアルキル基、または置換若しくは無置換のＣ６～１０アリール基を挙げることができる。 In the present invention, preferred X 3 is a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, or a substituted or unsubstituted C6-10 aryl group. can.
　直鎖Ｃ１～６アルキル基上の置換基、直鎖Ｃ２～６アルケニル基上の置換基、直鎖Ｃ２～６アルキニル基上の置換基、Ｃ３～６シクロアルキル基上の置換基、Ｃ６～１０アリール基上の置換基、または４～６員環のヘテロシクリル基上の置換基としては、以下の置換基群より選択される１または２以上の置換基を挙げることができる（以下、この置換基を記号「Ｇ」で表すことがある。）。
　また、置換基（Ｇ）は２以上ある場合、そのうちの２つが一緒になって二価の有機基を形成してもよい。以下に置換基群を示す。
　ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の３～１０員環のヘテロシクリル基、置換若しくは無置換の３～１０員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒａ－ＣＯ－で表される基、カルボキシ基、Ｒｂ－Ｏ－ＣＯ－で表される基、ＲｃＲｄＮ－で表される基、ＲｃＲｄＮ－ＣＯ－で表される基、ＲｃＲｄＮ－ＮＲｄ-ＣＯ－で表される基、ＲｂＳＯ２－ＮＲｄ-ＣＯ－で表される基、Ｒａ－ＣＯ－Ｏ－で表される基、Ｒａ－ＣＯ－ＮＲｅ－で表される基、Ｒａ－ＣＯ－ＣＯ－ＮＲｅ－で表される基、Ｒａ－ＣＯ－ＮＲｅ－ＮＲｅ－で表される基、Ｒａ－ＣＯ－ＮＲｅ－ＮＲｅ－ＣＯ－で表される基、Ｒｂ－Ｏ－ＣＯ－Ｏ－で表される基、Ｒｂ－Ｏ－ＣＯ－ＮＲｅ－で表される基、ＲｃＲｄＮ－ＣＯ－Ｏ－で表される基、ＲｃＲｄＮ－ＣＯ－ＮＲｅ－で表される基、ＲｃＲｄＮ－ＣＯ－ＣＯ－ＮＲｅ－で表される基、Ｒａ－ＣＳ－ＮＲｅ－で表される基、ＲｃＲｄＮ－ＣＳ－ＮＲｅ－で表される基、ＲｂＳＯ２－ＮＲｅ－で表される基、ＲｃＲｄＮ－ＳＯ２－で表される基、ＲａＯ－Ｎ＝ＣＲｆ－で表される基、ＲｈＲｊＣ＝Ｎ－Ｏ－で表される基、Ｒａ－Ｃ（＝ＮＲｇ）－ＮＲｅ－で表される基、ＲｃＲｄＮ－Ｃ（＝ＮＲｇ）－で表される基、ＲｈＲｉＳ（＝Ｏ）＝Ｎ－ＣＯ－で表される基、ＲｈＲｉＳ＝Ｎ－ＣＯ－で表される基。 Substituents on Linear C1-6 Alkyl Groups, Substituents on Linear C2-6 Alkenyl Groups, Substituents on Linear C2-6 Alkynyl Groups, Substituents on C3-6 Cycloalkyl Groups, C6-10 Examples of substituents on the aryl group or substituents on the 4- to 6-membered heterocyclyl group include one or more substituents selected from the following group of substituents (hereinafter, this substituent is sometimes represented by the symbol "G").
Moreover, when there are two or more substituents (G), two of them may combine to form a divalent organic group. Substituent groups are shown below.
halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1 ~ 6 alkylsulfonyl group, substituted or unsubstituted C3 ~ 6 cycloalkyl group, substituted or unsubstituted C3 ~ 6 cycloalkyloxy group, substituted or unsubstituted C6 ~ 10 aryl group, substituted or unsubstituted C6 ~10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3-10 membered ring heterocyclyl group, substituted or unsubstituted 3- to 10-membered heterocyclyloxy group, nitro group, cyano group, group represented by R a —CO—, carboxy group, R b —O—CO— a group represented by R c R d N—, a group represented by R c R d N—CO—, a group represented by R c R d N—NR d —CO—, R b SO 2 a group represented by -NR d -CO-, a group represented by R a -CO-O-, a group represented by R a -CO-NR e -, a group represented by R a -CO-CO-NR e - a group represented by R a -CO-NR e -NR e -, a group represented by R a -CO-NR e -NR e -CO-, R b -O-CO-O- A group represented by R b —O—CO—NR e — A group represented by R c R d N—CO—O— R c R d N—CO—NR e — A group represented by R c R d N—CO—CO—NR e — A group represented by R a —CS-NR e — R c R d N—CS-NR e — a group represented by R b SO 2 —NR e —, a group represented by R c R d N—SO 2 —, a group represented by R a ON=CR f —, R h R j A group represented by C=NO-, a group represented by R a -C(=NR g )-NR e -, a group represented by R c R d NC(=NR g )- a group represented by R h R i S(=O)=N--CO--, a group represented by R h R i S=N--CO--.
　上記の置換基群中、Ｒａは、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の３～１０員環のヘテロシクリル基を示す。
　Ｒｂは、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒｃは、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒｄは、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、または置換若しくは無置換のＣ６～１０アリール基を示し、ここで、ＲｃとＲｄは、一緒になって二価の有機基を形成してもよい。
　Ｒｅは、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｆは、水素原子、アミノ基、または置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｒｇは、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｈは、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｉは、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示し、ここで、ＲｈとＲｉは、一緒になって二価の有機基を形成してもよい。 In the above substituent groups, each R a is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 10-membered heterocyclyl group.
R b each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo It represents an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Each R c is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
R d each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group, R c and R d may together form a divalent organic group.
Each R e independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group.
R f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
Each R g independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Each R h independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group.
Each R i independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group, wherein R h and R i together form a divalent An organic group may be formed.
　Ｇにおける「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。 Examples of the "halogeno group" in G include a fluoro group, a chloro group, a bromo group, and an iodo group.
　Ｇにおける「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。
　Ｇにおける「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。 The "C1-6 alkyl group" for G may be linear or branched.
The "C1-6 alkyl group" in G includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s- Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
　Ｇにおける「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などを挙げることができる。 The "C2-6 alkenyl group" in G includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group , 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
　Ｇにおける「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などを挙げることができる。 The "C2-6 alkynyl group" in G includes an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group , 1,1-dimethyl-2-butynyl group, and the like.
　Ｇにおける「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、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、ｉ－ヘキシルオキシ基などを挙げることができる。
　Ｇにおける「Ｃ２～６アルケニルオキシ基」としては、ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などを挙げることができる。
　Ｇにおける「Ｃ２～６アルキニルオキシ基」としては、エチニルオキシ基、プロパルギルオキシ基などを挙げることができる。 The "C1-6 alkoxy group" for G includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, Examples include s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of the "C2-6 alkenyloxy group" for G include a vinyloxy group, an allyloxy group, a propenyloxy group and a butenyloxy group.
Examples of the "C2-6 alkynyloxy group" for G include an ethynyloxy group and a propargyloxy group.
　Ｇにおける「Ｃ１～６アルキルチオ基」としては、メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｎ－ブチルチオ基、ｎ－ペンチルチオ基、ｎ－ヘキシルチオ基、ｉ－プロピルチオ基などを挙げることができる。
　Ｇにおける「Ｃ１～６アルキルスルフィニル基」としては、メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などを挙げることができる。
　Ｇにおける「Ｃ１～６アルキルスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などを挙げることができる。 Examples of the "C1-6 alkylthio group" for G include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group and an i-propylthio group.
Examples of the "C1-6 alkylsulfinyl group" for G include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
Examples of the "C1-6 alkylsulfonyl group" for G include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.
　Ｇにおける「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」、「Ｃ１～６アルコキシ基」、「Ｃ２～６アルケニルオキシ基」、「Ｃ２～６アルキニルオキシ基」、「Ｃ１～６アルキルチオ基」、「Ｃ１～６アルキルスルフィニル基」、または「Ｃ１～６アルキルスルホニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；メチルチオ基、エチルチオ基などのＣ１～６アルキルチオ基：メチルスルフィニル基、エチルスルフィニル基などのＣ１～６アルキルスルフィニル基；メチルスルホニル基、エチルスルホニル基などのＣ１～６アルキルスルホニル基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；またはシアノ基が好ましい。 "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkynyloxy group" in G ”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” or “C1-6 alkylsulfonyl group” include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group. hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C1-6 alkylthio groups such as methylthio group and ethylthio group; C1- such as methylsulfinyl group and ethylsulfinyl group C1-6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; C6 such as phenyl group and naphthyl group ~10 aryl group; C1-6 alkyl group, C1-6 alkoxy such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group C6-10 aryl group substituted with one or more substituents selected from group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group , oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, 5-membered heteroaryl group such as tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 5-membered heteroaryl group substituted with one or more substituents selected from 6 haloalkyl groups or C1-6 haloalkoxy groups; 6-membered rings such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group 6-membered heteroaryl group substituted with any one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group Aryl groups; or cyano groups are preferred.
　Ｇにおける「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｇにおける「Ｃ３～６シクロアルキルオキシ基」としては、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などを挙げることができる。 Examples of the "C3-6 cycloalkyl group" for G include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the "C3-6 cycloalkyloxy group" for G include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
　Ｇにおける「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基などを挙げることができる。
　Ｇにおける「Ｃ６～１０アリールオキシ基」としては、フェノキシ基、ナフトキシ基などを挙げることができる。 Examples of the "C6-10 aryl group" for G include a phenyl group and a naphthyl group.
Examples of the "C6-10 aryloxy group" for G include a phenoxy group and a naphthoxy group.
　Ｇにおける「Ｃ６～１０アリールチオ基」としては、フェニルチオ基、ナフチルチオ基などを挙げることができる。
　Ｇにおける「Ｃ６～１０アリールスルフィニル基」としては、フェニルスルフィニル基、ナフチルスルフィニル基などを挙げることができる。
　Ｇにおける「Ｃ６～１０アリールスルホニル基」としては、フェニルスルホニル基、ナフチルスルホニル基などを挙げることができる。 Examples of the "C6-10 arylthio group" for G include a phenylthio group and a naphthylthio group.
Examples of the "C6-10 arylsulfinyl group" for G include a phenylsulfinyl group and a naphthylsulfinyl group.
Examples of the "C6-10 arylsulfonyl group" for G include a phenylsulfonyl group and a naphthylsulfonyl group.
　Ｇにおける「３～１０員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１、２、３または４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。単環および多環のいずれでもよい。
　「３～１０員環のヘテロシクリル基」としては、３～６員環の飽和ヘテロシクリル基、５～１０員環のヘテロアリール基、５～１０員環の部分不飽和ヘテロシクリル基などを挙げることができる。 The "3- to 10-membered heterocyclyl group" for G is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic.
Examples of the "3- to 10-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .
　３～６員環の飽和ヘテロシクリル基としては、アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～１０員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；インドリル基、イソインドリル基、ベンゾフラニル基、ベンゾチエニル基、インダゾリル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾイソオキサオゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基などの９員ヘテロアリール基；キノリニル基、イソキノリニル基、シンノリニル基、フタラジニル基、キナゾリニル基、キノキサリニル基などの１０員ヘテロアリール基；を挙げることができる。
　５～１０員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基；インドリニル基、イソインドリニル基、２，３－ジヒドロベンゾフラニル基、１，３－ジヒドロベンゾフラニル基などの９員環の部分不飽和ヘテロシクリル基；１，２，３，４－テトラヒドロキノリニル基などの１０員環の部分不飽和ヘテロシクリル基；を挙げることができる。 3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, A dioxolanyl group, a dioxanyl group and the like can be mentioned.
Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc. 10-membered heteroaryl group;
Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl group; 9-membered partially unsaturated ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;
　Ｇにおける「３～１０員環のヘテロシクリルオキシ基」は、３～１０員環のヘテロシクリル基とオキシ基が結合した構造を有する。具体例としては、チアゾリルオキシ基、ピリジルオキシ基などを挙げることができる。 The "3- to 10-membered heterocyclyloxy group" in G has a structure in which a 3- to 10-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.
　Ｇにおける「Ｃ３～６シクロアルキル基」、「Ｃ３～６シクロアルキルオキシ基」、「Ｃ６～１０アリール基」、「Ｃ６～１０アリールオキシ基」、「Ｃ６～１０アリールチオ基」、「Ｃ６～１０アリールスルフィニル基」、「Ｃ６～１０アリールスルホニル基」、「３～１０員環のヘテロシクリル基」、または「３～１０員環のヘテロシクリルオキシ基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；Ｃ３～６シクロアルキルＣ１～６アルコキシ基；Ｃ６～１０アリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルコキシ基；５員環のヘテロアリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール）Ｃ１～６アルコキシ基；６員環のヘテロアリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール）Ｃ１～６アルコキシ基；メチルチオ基、エチルチオ基などのＣ１～６アルキルチオ基：メチルスルフィニル基、エチルスルフィニル基などのＣ１～６アルキルスルフィニル基；メチルスルホニル基、エチルスルホニル基などのＣ１～６アルキルスルホニル基；トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基：トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；シクロプロピル基、シクロブチル基などのＣ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、またはシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；Ｃ３～６シクロアルケニル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基などの３～４員環の飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された３～４員環の飽和ヘテロシクリル基；ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などの５～６員環の飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環の飽和ヘテロシクリル基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和へテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環の部分飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環の部分飽和ヘテロシクリル基；
ＲＧ１－ＣＯ－で表される基　（式中、ＲＧ１は、水素原子；Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；Ｃ２～６アルケニル基；Ｃ２～６ハロアルケニル基；Ｃ２～６アルキニル基；Ｃ２～６ハロアルキニル基；Ｃ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、若しくはシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；Ｃ６～１０アリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；５～６員環のヘテロアリール基；または；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール基；を示す。以下のＲＧ１においても同じ。）；
カルボキシ基；
ＲＧ２－Ｏ－ＣＯ－で表される基　（式中、ＲＧ２は、Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；Ｃ２～６アルケニル基；Ｃ２～６ハロアルケニル基；Ｃ２～６アルキニル基；Ｃ２～６ハロアルキニル基；Ｃ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、若しくはシアノ基で置換されたＣ３～６シクロアルキル基；Ｃ６～１０アリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；５～６員環のヘテロアリール基；または；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール基；を示す。以下のＲＧ２においても同じ。）；
ＲＧ１ＲＧ１Ｎ－で表される基（式中のＲＧ１は同一でも異なっていてもよい。ＲＧ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ＲＧ１ＲＧ１Ｎ－ＣＯ－で表される基（式中のＲＧ１は同一でも異なっていてもよい。ＲＧ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ＲＧ１－ＣＯ－Ｏ－で表される基；ＲＧ１－ＣＯ－ＮＲＧ３－で表される基（式中、ＲＧ３は、水素原子；Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；または（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；を示す。以下のＲＧ３においても同じ。）；
ＲＧ２－Ｏ－ＣＯ－Ｏ－で表される基；ＲＧ２－Ｏ－ＣＯ－ＮＲＧ３－で表される基；ＲＧ１ＲＧ１Ｎ－ＣＯ－Ｏ－で表される基（式中のＲＧ１は同一でも異なっていてもよい。ＲＧ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ＲＧ１ＲＧ１Ｎ－ＣＯ－ＮＲＧ３－で表される基（式中のＲＧ１は同一でも異なっていてもよい。ＲＧ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；ＲＧ２ＳＯ２－ＮＲＧ３－で表される基；ＲＧ１ＲＧ１Ｎ－ＳＯ２－で表される基（式中のＲＧ１は同一でも異なっていてもよい。ＲＧ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ＲＧ１－Ｏ－Ｎ＝Ｃ（ＲＧ４）－で表される基（式中、ＲＧ４は、水素原子またはＣ１～６アルキル基を示す。）；（ＲＧ１）２Ｃ＝Ｎ－Ｏ－で表される基（式中のＲＧ１は同一でも異なっていてもよい。ＲＧ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ペンタフルオロスルファニル基、ニトロ基、またはシアノ基が好ましい。
さらに、「Ｃ３～６シクロアルキル基」、「Ｃ３～６シクロアルキルオキシ基」、「３～１０員環のヘテロシクリル基」、または「３～１０員環のヘテロシクリルオキシ基」上の置換基としては、オキソ基も好ましい。 "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10" in G Arylsulfinyl group", "C6-10 arylsulfonyl group", "3- to 10-membered heterocyclyl group" or "3- to 10-membered heterocyclyloxy group" include a fluoro group, a chloro group, halogeno groups such as bromo group and iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group , C1-6 alkyl groups such as n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro - n-propoxy group, 2,3-dichlorobutoxy group, C1 ~ 6 haloalkoxy group such as trifluoromethoxy group; C3 ~ 6 cycloalkyl C1 ~ 6 alkoxy group; C6 ~ 10 aryl C1 ~ 6 alkoxy group; (C1 ~6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents C6-10 aryl)C1-6 alkoxy group; 5-membered heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group with one or more substituents substituted 5-membered heteroaryl) C1-6 alkoxy group; 6-membered heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or 6-membered ring heteroaryl substituted with one or more substituents of any C1-6 haloalkoxy group) C1-6 alkoxy group; methylthio group, C1-6 alkylthio group such as ethylthio group: methylsulfinyl group, ethyl C1-6 alkylsulfinyl group such as sulfinyl group; C1-6 alkylsulfonyl group such as methylsulfonyl group and ethylsulfonyl group; C such as trifluoromethylthio group and 2,2,2-trifluoroethylthio group 1-6 haloalkylthio group: C1-6 haloalkylsulfinyl group such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group C1-6 haloalkylsulfonyl group such as; C3-6 cycloalkyl group such as cyclopropyl group and cyclobutyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy a C3-6 cycloalkyl group substituted with one or more substituents, or a cyano group; a C3-6 cycloalkenyl group; a phenyl group, a C6-10 aryl group such as a naphthyl group; a 4-methylphenyl group, C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups such as 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, or a C6-10 aryl group substituted with any one or more substituents of a C1-6 haloalkoxy group; an aziridinyl group, an epoxy group, an azetidinyl group, a 3- to 4-membered saturated heterocyclyl group such as an oxetanyl group; 3- to 4-membered saturated heterocyclyl group substituted with one or more substituents selected from a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; pyrrolidinyl group , tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, 5- to 6-membered saturated heterocyclyl group such as dioxanyl group; C1-6 alkyl group, C1-6 5- to 6-membered saturated heterocyclyl group substituted with one or more substituents selected from an alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a pyrrolyl group, a furyl group, a thienyl group, 5-membered ring heteroaryl groups such as imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, 5-membered heteroaryl group substituted with one or more substituents selected from a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; 6-membered heteroaryl group such as dazinyl group and triazinyl group; substitution of any one or more of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 6-membered heteroaryl group substituted with a group; pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, 5-membered partially unsaturated heterocyclyl group such as isoxazolinyl group; 5-membered ring partially saturated heterocyclyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; dihydropyranyl 6-membered ring partially unsaturated heterocyclyl group such as group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group with one or more substituents a substituted 6-membered partially saturated heterocyclyl group;
a group represented by R G1 —CO— (wherein R G1 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, C1-6 alkyl group substituted with one or more substituents of a phenyl group or a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a haloalkyl group or a C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from ∼6 haloalkyl group or C1-6 haloalkoxy group)C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or a C3-6 cycloalkyl group substituted with one or more substituents of a cyano group; a C6-10 aryl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or C6-10 aryl group substituted with one or more substituents of any one of C1-6 haloalkoxy groups; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, a 5- to 6-membered heteroaryl group substituted with one or more substituents; The same applies to R G1 below.);
carboxy group;
A group represented by R G2 —O—CO— (wherein R G2 is a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl or a C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl C6-10 aryl)C1-6 alkyl group substituted with one or more substituents, or C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from a 6-haloalkyl group or a C1-6 haloalkoxy group) C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl group C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or C3-6 cycloalkyl group substituted with cyano group; C6-10 aryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group a C6-10 aryl group substituted with one or more substituents; a 5- to 6-membered heteroaryl group; or; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1 A 5- to 6-membered heteroaryl group substituted with one or more substituents selected from any one of up to 6 haloalkoxy groups; The same applies to R G2 below.);
A group represented by R G1 R G1 N- (R G1 in the formula may be the same or different. R G1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.);
A group represented by R G1 R G1 N—CO— (R G1 in the formula may be the same or different. R G1 together may be a trimethylene group, tetramethylene group, pentamethylene group, or A methyleneoxydimethylene group may be formed.);
a group represented by R G1 -CO-O-; a group represented by R G1 -CO-NR G3 - (wherein R G3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; The same applies to R G3 below.);
A group represented by R G2 -O-CO-O-; a group represented by R G2 -O-CO-NR G3 -; a group represented by R G1 R G1 N-CO-O- (in the formula R G1 may be the same or different, and R G1 may together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
A group represented by R G1 R G1 N—CO—NR G3 — (in the formula, R G1 may be the same or different; R G1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, , or may form a dimethyleneoxydimethylene group); a group represented by R G2 SO 2 —NR G3 —; a group represented by R G1 R G1 N—SO 2 — (in the formula, R G1 may be the same or different, and R G1 together may form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group);
a group represented by R G1 -ON=C(R G4 )- (wherein R G4 represents a hydrogen atom or a C1-6 alkyl group); (R G1 ) 2 C=N-O- A group represented by (R 1 G1 in the formula may be the same or different. RG1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.);
A pentafluorosulfanyl group, a nitro group, or a cyano group are preferred.
Furthermore, as a substituent on the "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "3- to 10-membered heterocyclyl group", or "3- to 10-membered heterocyclyloxy group" , oxo groups are also preferred.
　Ｇにおける「Ｒａ－ＣＯ－で表される基」中、Ｒａは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の３～１０員環のヘテロシクリル基を示す。 In the "group represented by R a -CO-" for G, R a is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted It represents a C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 10-membered heterocyclyl group.
　Ｒａにおける「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。
　Ｒａにおける「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基などを挙げることができる。
　Ｒａにおける「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基などを挙げることができる。
　Ｒａにおける「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、または「Ｃ２～６アルキニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；メチルチオ基、エチルチオ基などのＣ１～６アルキルチオ基：メチルスルフィニル基、エチルスルフィニル基などのＣ１～６アルキルスルフィニル基；メチルスルホニル基、エチルスルホニル基などのＣ１～６アルキルスルホニル基；カルボキシ基；メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などのＣ１～６アルコキシカルボニル基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；またはシアノ基が好ましい。 The "C1-6 alkyl group" for R a includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Examples of the “C2-6 alkenyl group” for R a include a vinyl group and a 1-propenyl group.
Examples of the “C2-6 alkynyl group” for R a include an ethynyl group and a 1-propynyl group.
Examples of substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in R a include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C1-6 alkylthio groups such as methylthio group and ethylthio group; C1-6 groups such as methylsulfinyl group and ethylsulfinyl group alkylsulfinyl group; methylsulfonyl group, C1-6 alkylsulfonyl group such as ethylsulfonyl group; carboxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t -C1 ~ 6 alkoxycarbonyl group such as butoxycarbonyl group; C3 ~ 6 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; C6 ~ 10 aryl group such as phenyl group and naphthyl group; 4-methyl phenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc., C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl group substituted with one or more substituents selected from haloalkyl group or C1-6 haloalkoxy group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl 5-membered ring heteroaryl group such as group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 5-membered heteroaryl group substituted with any one or more substituents of haloalkoxy group; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group; C1-6 a 6-membered heteroaryl group substituted with one or more substituents selected from an alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or cyano groups are preferred.
　Ｒａにおける「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｒａにおける「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インデニル基、インダニル基、テトラリニル基などを挙げることができる。 Examples of the “C3-6 cycloalkyl group” for R a include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the “C6-10 aryl group” for R a include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.
　Ｒａにおける「３～１０員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１、２、３または４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。単環および多環のいずれでもよい。
　「３～１０員環のヘテロシクリル基」としては、３～６員環の飽和ヘテロシクリル基、５～１０員環のヘテロアリール基、５～１０員環の部分不飽和ヘテロシクリル基などを挙げることができる。
　３～６員環の飽和ヘテロシクリル基としては、アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～１０員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；インドリル基、イソインドリル基、ベンゾフラニル基、ベンゾチエニル基、インダゾリル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾイソオキサオゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基などの９員ヘテロアリール基；キノリニル基、イソキノリニル基、シンノリニル基、フタラジニル基、キナゾリニル基、キノキサリニル基などの１０員ヘテロアリール基；を挙げることができる。
　５～１０員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基；インドリニル基、イソインドリニル基、２，３－ジヒドロベンゾフラニル基、１，３－ジヒドロベンゾフラニル基などの９員環の部分不飽和ヘテロシクリル基；１，２，３，４－テトラヒドロキノリニル基などの１０員環の部分不飽和ヘテロシクリル基；を挙げることができる。 The “3- to 10-membered heterocyclyl group” for R a is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different. It may be monocyclic or polycyclic.
Examples of the "3- to 10-membered heterocyclyl group" include a 3- to 6-membered saturated heterocyclyl group, a 5- to 10-membered heteroaryl group, a 5- to 10-membered partially unsaturated heterocyclyl group, and the like. .
3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, Dioxolanyl group, dioxanyl group and the like can be mentioned.
Examples of 5- to 10-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. 5-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl 6-membered heteroaryl groups; indolyl, isoindolyl, benzofuranyl, benzothienyl, indazolyl, 9-membered heteroaryl groups such as benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, and benzisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc. 10-membered heteroaryl group;
Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro 6-membered partially unsaturated heterocyclyl group such as pyranyl group; 9-membered partially unsaturated ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group heterocyclyl group; 10-membered ring partially unsaturated heterocyclyl group such as 1,2,3,4-tetrahydroquinolinyl group;
　Ｒａにおける「Ｃ３～６シクロアルキル基」、「Ｃ６～１０アリール基」、または「３～１０員環のヘテロシクリル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；Ｃ３～６シクロアルキルＣ１～６アルコキシ基；Ｃ６～１０アリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルコキシ基；５員環のヘテロアリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール）Ｃ１～６アルコキシ基；６員環のヘテロアリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール）Ｃ１～６アルコキシ基；メチルチオ基、エチルチオ基などのＣ１～６アルキルチオ基：メチルスルフィニル基、エチルスルフィニル基などのＣ１～６アルキルスルフィニル基；メチルスルホニル基、エチルスルホニル基などのＣ１～６アルキルスルホニル基；トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基：トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；シクロプロピル基、シクロブチル基、シクロペンチル基などのＣ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、またはシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；Ｃ３～６シクロアルケニル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基などの３～４員環の飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された３～４員環の飽和ヘテロシクリル基；ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などの５～６員環の飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環の飽和ヘテロシクリル基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和へテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環の部分飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環の部分飽和ヘテロシクリル基； 
Ｒｑ１－ＣＯ－で表される基　（式中、Ｒｑ１は、水素原子；Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；Ｃ２～６アルケニル基；Ｃ２～６ハロアルケニル基；Ｃ２～６アルキニル基；Ｃ２～６ハロアルキニル基；Ｃ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、若しくはシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；Ｃ６～１０アリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；５～６員環のヘテロアリール基；または；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール基；を示す。以下のＲｑ１においても同じ。）；
カルボキシ基；
Ｒｑ２－Ｏ－ＣＯ－で表される基　（式中、Ｒｑ２は、Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；Ｃ２～６アルケニル基；Ｃ２～６ハロアルケニル基；Ｃ２～６アルキニル基；Ｃ２～６ハロアルキニル基；Ｃ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、若しくはシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；Ｃ６～１０アリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；５～６員環のヘテロアリール基；または；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール基；を示す。以下のＲｑ２において同じ。）；
Ｒｑ１Ｒｑ１Ｎ－で表される基（式中のＲｑ１は同一でも異なっていてもよい。Ｒｑ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
Ｒｑ１Ｒｑ１Ｎ－ＣＯ－で表される基（式中のＲｑ１は同一でも異なっていてもよい。Ｒｑ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
Ｒｑ１－ＣＯ－Ｏ－で表される基；Ｒｑ１－ＣＯ－ＮＲｑ３－で表される基（式中、Ｒｑ３は、水素原子；Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；または（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；を示す。以下のＲｑ３において同じ。）；
Ｒｑ２－Ｏ－ＣＯ－Ｏ－で表される基；Ｒｑ２－Ｏ－ＣＯ－ＮＲｑ３－で表される基；Ｒｑ１Ｒｑ１Ｎ－ＣＯ－Ｏ－で表される基（式中のＲｑ１は同一でも異なっていてもよい。Ｒｑ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
Ｒｑ１Ｒｑ１Ｎ－ＣＯ－ＮＲｑ３－で表される基（式中のＲｑ１は同一でも異なっていてもよい。Ｒｑ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；Ｒｑ２ＳＯ２－ＮＲｑ３－で表される基；Ｒｑ１Ｒｑ１Ｎ－ＳＯ２－で表される基（式中のＲｑ１は同一でも異なっていてもよい。Ｒｑ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
Ｒｑ１－Ｏ－Ｎ＝Ｃ（Ｒｑ４）－で表される基（式中、Ｒｑ４は、水素原子またはＣ１～６アルキル基を示す。）；（Ｒｑ１）２Ｃ＝Ｎ－Ｏ－で表される基（式中のＲｑ１は同一でも異なっていてもよい。Ｒｑ１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、またはジメチレンオキシジメチレン基を形成してもよい。）；
ペンタフルオロスルファニル基、ニトロ基、またはシアノ基が好ましい。
　さらに、「Ｃ３～６シクロアルキル基」、または「３～１０員環のヘテロシクリル基」上の置換基としては、オキソ基も好ましい。 Substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "3- to 10-membered heterocyclyl group" for R a include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. C1 ~ 6 alkyl group of; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, C1 ~ 6 haloalkyl group such as 1-fluoro-n-butyl group; hydroxyl group; methoxy group , ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy groups such as t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1-6 haloalkoxy group such as trifluoromethoxy group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10 aryl C1-6 alkoxy group; (C1-6 alkyl group, C1 ~6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents C6-10 aryl)C1-6 alkoxy group; 5-membered ring heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group 5-membered ring substituted with one or more substituents heteroaryl) C1-6 alkoxy group; 6-membered heteroaryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy 6-membered ring heteroaryl substituted with one or more substituents) C1-6 alkoxy group; C1-6 alkylthio group such as methylthio group and ethylthio group; C1- such as methylsulfinyl group and ethylsulfinyl group 6 alkylsulfinyl group; methylsulfonyl group, C1-6 alkylsulfonyl group such as ethylsulfonyl group; trifluoromethylthio group, C1-6 haloalkylthio group such as 2,2,2-trifluoroethylthio group: trifluoromethylsulfinyl a C1-6 haloalkylsulfinyl group such as a 2,2,2-trifluoroethylsulfinyl group; a trifluoromethylsulfonyl group; a 2,2,2-trifluoroethyls C1-6 haloalkylsulfonyl group such as sulphonyl group; C3-6 cycloalkyl group such as cyclopropyl group, cyclobutyl group and cyclopentyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, a C1-6 haloalkoxy group, or a C3-6 cycloalkyl group substituted with one or more substituents of a cyano group; a C3-6 cycloalkenyl group; a phenyl group, a C6-10 aryl group such as a naphthyl group; -C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 such as methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group C6-10 aryl group substituted with one or more substituents selected from ∼6 haloalkyl groups or C1-6 haloalkoxy groups; saturated 3- to 4-membered rings such as aziridinyl groups, epoxy groups, azetidinyl groups and oxetanyl groups; Heterocyclyl group; saturated 3- to 4-membered ring substituted with one or more substituents selected from C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group heterocyclyl group; pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and other 5- to 6-membered saturated heterocyclyl groups; C1-6 alkyl a 5- to 6-membered saturated heterocyclyl group substituted with one or more substituents selected from a group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; pyrrolyl group, furyl five-membered ring heteroaryl groups such as groups, thienyl groups, imidazolyl groups, pyrazolyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, triazolyl groups, oxadiazolyl groups, thiadiazolyl groups, tetrazolyl groups; C1-6 alkyl groups, C1 ~6 alkoxy group, halogeno group, C1-6 haloalkyl group, or 5-membered heteroaryl group substituted with one or more substituents of C1-6 haloalkoxy group; pyridyl group, pyrazinyl group, pyrimidinyl group, 6-membered heteroaryl group such as pyridazinyl group and triazinyl group; substitution of one or more of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group at base Substituted 6-membered heteroaryl group; 5-membered partially unsaturated heterocyclyl group such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group; C1-6 alkyl a 5-membered ring partially saturated heterocyclyl group substituted with one or more substituents selected from a group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a dihydropyranyl group, etc. 6-membered partially unsaturated heterocyclyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group substituted with one or more substituents a six-membered ring partially saturated heterocyclyl group;
a group represented by R q1 —CO— (wherein R q1 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, C1-6 alkyl group substituted with one or more substituents of a phenyl group or a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a haloalkyl group or a C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from ∼6 haloalkyl group or C1-6 haloalkoxy group)C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or a C3-6 cycloalkyl group substituted with one or more substituents of a cyano group; a C6-10 aryl group; a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or C6-10 aryl group substituted with one or more substituents of any one of C1-6 haloalkoxy groups; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , a 5- to 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 haloalkyl group or a C1-6 haloalkoxy group; The same applies to R q1 below.);
carboxy group;
A group represented by R q2 —O—CO— (wherein R q2 is a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl or a C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl C6-10 aryl)C1-6 alkyl group substituted with one or more substituents, or C1-6 haloalkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 5- to 6-membered ring heteroaryl substituted with one or more substituents selected from a 6-haloalkyl group or a C1-6 haloalkoxy group) C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl group C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, or C3-6 cycloalkyl group substituted with any one or more substituents of cyano group; C6-10 aryl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1 C6-10 aryl group substituted with any one or more substituents of ~6 haloalkoxy group; 5- to 6-membered heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, a 5- to 6-membered heteroaryl group substituted with one or more substituents selected from a C1-6 haloalkyl group or a C1-6 haloalkoxy group; the same applies to R q2 below.);
A group represented by R q1 R q1 N- (R q1 in the formula may be the same or different. R q1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.);
A group represented by R q1 R q1 N—CO— (R q1 in the formula may be the same or different. Together, R q1 may be a trimethylene group, a tetramethylene group, a A methyleneoxydimethylene group may be formed.);
a group represented by R q1 —CO—O—; a group represented by R q1 —CO—NR q3 — (wherein R q3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered heteroaryl substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group) C1-6 alkyl group; The same applies to R q3 below.);
A group represented by R q2 —O—CO—O—; a group represented by R q2 —O—CO—NR q3 —; a group represented by R q1 R q1 N—CO—O— (in the formula R q1 may be the same or different, and R q1 may be combined to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.);
A group represented by R q1 R q1 N—CO—NR q3 — (in the formula, R q1 may be the same or different. R q1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, , or may form a dimethyleneoxydimethylene group); a group represented by R q2 SO 2 —NR q3 —; a group represented by R q1 R q1 N—SO 2 — (in the formula, R q1 may be the same or different, and R q1 may be combined to form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group.);
a group represented by R q1 -ON=C(R q4 )- (wherein R q4 represents a hydrogen atom or a C1-6 alkyl group); (R q1 ) 2 C=N-O- (R q1 in the formula may be the same or different. R q1 together form a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxydimethylene group. may be used.);
A pentafluorosulfanyl group, a nitro group, or a cyano group are preferred.
Furthermore, an oxo group is also preferred as a substituent on the "C3-6 cycloalkyl group" or the "3- to 10-membered heterocyclyl group".
　「Ｒａ－ＣＯ－で表される基」の具体例としては、ホルミル基、アセチル基、ｉ－プロピルカルボニル基などを挙げることができる。 Specific examples of the "group represented by R a -CO-" include a formyl group, an acetyl group, an i-propylcarbonyl group and the like.
　Ｇにおける「Ｒｂ－Ｏ－ＣＯ－で表される基」中、Ｒｂは、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒｂにおける置換基の具体例は、Ｒａにおいて例示したものと同じものを挙げることができる。 In the "group represented by R b -O-CO-" for G, R b is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ~6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Specific examples of the substituent for R b are the same as those exemplified for R a .
　「Ｒｂ－Ｏ－ＣＯ－で表される基」の具体例としては、メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などを挙げることができる。 Specific examples of the "group represented by R b -O-CO-" include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group and a t-butoxycarbonyl group. and the like.
　Ｇにおける「ＲｃＲｄＮ－で表される基」中、Ｒｃは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、Ｒｄは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　ＲｃまたはＲｄにおける置換基の具体例は、Ｒａにおいて例示したものと同じものを挙げることができる。
　Ｒｄにおける「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、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、ｉ－ヘキシルオキシ基などを挙げることができる。
　Ｒｄにおける「Ｃ１～６アルコキシ基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；またはシアノ基が好ましい。 In the "group represented by R c R d N-" for G, R c is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted A C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and R d is , a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of substituents for R c or R d are the same as those exemplified for R a .
The "C1-6 alkoxy group" in R d includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, and an i-butoxy group. , s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of substituents on the "C1-6 alkoxy group" in R d include halogeno groups such as fluoro, chloro, bromo and iodo groups; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group , n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, etc. C1 ~ 6 haloalkoxy group of; cyclopropyl group, cyclobutyl group, cyclopentyl group, C3 ~ 6 cycloalkyl group such as cyclohexyl group; phenyl group, C6 ~ 10 aryl group such as naphthyl group; 4-methylphenyl group, 4- C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1 such as methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group A C6-10 aryl group substituted with any one or more substituents of up to 6 haloalkoxy groups; or a cyano group is preferred.
　ここで、ＲｃとＲｄは、一緒になって二価の有機基を形成してもよい。
　形成できる二価の有機基としては、置換若しくは無置換のＣ２～５アルキレン基、置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基、置換若しくは無置換のＣ１～３アルキレンチオＣ１～３アルキレン基、または置換若しくは無置換のＣ１～３アルキレンイミノＣ１～３アルキレン基などを挙げることができる。
　さらに、－ＣＨ２ＣＨ２－Ｓｉ（ＣＨ３）２－ＣＨ２ＣＨ２－などのケイ素含有の２価炭化水素基を挙げることができる。
　「Ｃ２～５アルキレン基」としては、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンチオＣ１～３アルキレン基」としては、ジメチレンチオジメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンイミノＣ１～３アルキレン基」としては、ジメチレンイミノジメチレン基、などを挙げることができる。
　ここで、「Ｃ１～３アルキレンアルキレンイミノＣ１～３アルキレン基」のイミノ基とは、－ＮＨ－を意味する。
　「Ｃ２～５アルキレン基」、「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」、「Ｃ１～３アルキレンチオＣ１～３アルキレン基」及び「Ｃ１～３アルキレンイミノＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；メチリデン基；またはクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。 Here, R c and R d may together form a divalent organic group.
Examples of divalent organic groups that can be formed include a substituted or unsubstituted C2-5 alkylene group, a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group, a substituted or unsubstituted C1-3 alkylenethio C1-3 Examples include an alkylene group, or a substituted or unsubstituted C1-3 alkyleneimino C1-3 alkylene group.
Additionally, mention may be made of silicon-containing divalent hydrocarbon groups such as -CH 2 CH 2 -Si(CH 3 ) 2 -CH 2 CH 2 -.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of the "C1-3 alkylenethio C1-3 alkylene group" include a dimethylenethiodimethylene group and the like.
Examples of the "C1-3 alkyleneimino C1-3 alkylene group" include a dimethyleneiminodimethylene group and the like.
Here, the imino group of "C1-3 alkylenealkyleneimino C1-3 alkylene group" means -NH-.
Substituents on "C2-5 alkylene group", "C1-3 alkyleneoxy C1-3 alkylene group", "C1-3 alkylenethio C1-3 alkylene group" and "C1-3 alkyleneimino C1-3 alkylene group" Examples include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodine group; C1-6 alkyl group such as t-butyl group; methylidene group; or C1 such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group ~6 haloalkyl groups are preferred.
　「ＲｃＲｄＮ－で表される基」の具体例としては、アミノ基、メチルアミノ基、ジメチルアミノ基、ｉ－プロピルアミノ基などを挙げることができる。 Specific examples of the “group represented by R c R d N—” include amino group, methylamino group, dimethylamino group, i-propylamino group and the like.
　Ｇにおける「ＲｃＲｄＮ－ＣＯ－で表される基」中、ＲｃおよびＲｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。
　「ＲｃＲｄＮ－ＣＯ－で表される基」の具体例としては、カルバモイル基、Ｎ，Ｎ－ジメチルアミノカルボニル基、Ｎ－（ｉ－プロピル）アミノカルボニル基、Ｎ－（ｉ－プロピル）－Ｎ－メチルアミノカルボニル基などを挙げることができる。 In the “group represented by R c R d N—CO—” for G, R c and R d have the same meanings as those in the above “group represented by R c R d N—”.
Specific examples of the “group represented by R c R d N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, an N-(i-propyl )—N-methylaminocarbonyl group and the like.
　Ｇにおける「ＲｃＲｄＮ－ＮＲｄ－ＣＯ－で表される基」中、ＲｃおよびＲｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。
　「ＲｃＲｄＮ－ＮＲｄ－ＣＯ－で表される基」の具体例としては、２，２－ジメチルヒドラジン－１－カルボニル基などを挙げることができる。
　Ｇにおける「ＲｂＳＯ２－ＮＲｄ-ＣＯ－で表される基」中、Ｒｂは上記の「Ｒｂ－Ｏ－ＣＯ－で表される基」におけるそれらと同様の意味を示し、Ｒｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。
　「ＲｂＳＯ２－ＮＲｄ-ＣＯ－で表される基」の具体例としては、（メチルスルホニル）カルバモイル基、（シクロプロピルスルホニル）カルバモイル基、（（１－メチルシクロプロピル）スルホニル）カルバモイル基などを挙げることができる。 In the “group represented by R c R d N—NR d —CO—” for G, R c and R d have the same meanings as those in the above “group represented by R c R d N—” show.
Specific examples of the “group represented by R c R d N—NR d —CO—” include a 2,2-dimethylhydrazine-1-carbonyl group.
In the “group represented by R b SO 2 —NR d —CO—” for G, R b has the same meaning as in the above “group represented by R b —O—CO—”; d has the same meaning as in the above “group represented by R c R d N—”.
Specific examples of the "group represented by R b SO 2 -NR d -CO-" include a (methylsulfonyl)carbamoyl group, a (cyclopropylsulfonyl)carbamoyl group, and a ((1-methylcyclopropyl)sulfonyl)carbamoyl group. etc. can be mentioned.
　Ｇにおける「Ｒａ－ＣＯ－Ｏ－で表される基」中、Ｒａは上記の「Ｒａ－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ－ＣＯ－Ｏ－で表される基」の具体例としては、アセチルオキシ基などを挙げることができる。 In the "group represented by R a -CO-O-" for G, R a has the same meaning as in the above "group represented by R a -CO-".
Specific examples of the "group represented by R a -CO-O-" include an acetyloxy group.
　Ｇにおける「Ｒａ－ＣＯ－ＮＲｅ－で表される基」中、Ｒａは上記の「Ｒａ－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　Ｒｅは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｅにおける置換基の具体例は、Ｒａにおいて例示したものと同じものを挙げることができる。
　「Ｒａ－ＣＯ－ＮＲｅ－で表される基」の具体例としては、アセチルアミノ基、プロピオニルアミノ基、ブチリルアミノ基、ｉ－プロピルカルボニルアミノ基などを挙げることができる。 In the "group represented by R a -CO-NR e -" for G, R a has the same meaning as in the above "group represented by R a -CO-".
R e represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent for R e are the same as those exemplified for R a .
Specific examples of the "group represented by R a -CO-NR e -" include an acetylamino group, a propionylamino group, a butyrylamino group, an i-propylcarbonylamino group and the like.
　Ｇにおける「Ｒａ－ＣＯ－ＣＯ－ＮＲｅ－で表される基」中、Ｒａは上記の「Ｒａ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅは、上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ－ＣＯ－ＣＯ－ＮＲｅ－で表される基」の具体例としては、オキソプロパンアミド基などを挙げることができる。 In the "group represented by R a -CO-CO-NR e -" for G, R a has the same meaning as in the above "group represented by R a -CO-". R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Specific examples of the “group represented by R a —CO—CO—NR e —” include an oxopropanamide group.
　Ｇにおける「Ｒａ－ＣＯ－ＮＲｅ－ＮＲｅ－で表される基」中、Ｒａは上記の「Ｒａ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅは、上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ－ＣＯ－ＮＲｅ－ＮＲｅ－で表される基」の具体例としては、アセチルヒドラジニル基、ｉ－プロピルカルボニルヒドラジニル基などを挙げることができる。 In the "group represented by R a -CO-NR e -NR e -" for G, R a has the same meaning as in the above "group represented by R a -CO-". R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Specific examples of the “group represented by R a —CO—NR e —NR e —” include an acetylhydrazinyl group and an i-propylcarbonylhydrazinyl group.
　Ｇにおける「Ｒａ－ＣＯ－ＮＲｅ－ＮＲｅ－ＣＯ－で表される基」中、Ｒａは上記の「Ｒａ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅは、上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ－ＣＯ－ＮＲｅ－ＮＲｅ－ＣＯ－で表される基」の具体例としては、２－アセチルヒドラジン－１－カルボニル基などを挙げることができる。 In the "group represented by R a -CO-NR e -NR e -CO-" for G, R a has the same meaning as in the above "group represented by R a -CO-". R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Specific examples of the "group represented by R a -CO-NR e -NR e -CO-" include 2-acetylhydrazine-1-carbonyl group.
　Ｇにおける「Ｒｂ－Ｏ－ＣＯ－Ｏ－で表される基」中、Ｒｂは上記の「Ｒｂ－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒｂ－Ｏ－ＣＯ－Ｏ－で表される基」の具体例としては、メトキシカルボニルオキシ基、エトキシカルボニルオキシ基などを挙げることができる。 In the “group represented by R b —O—CO—O—” for G, R b has the same meaning as in the above “group represented by R b —O—CO—”.
Specific examples of the “group represented by R b —O—CO—O—” include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.
　Ｇにおける「Ｒｂ－Ｏ－ＣＯ－ＮＲｅ－で表される基」中、Ｒｂは上記の「Ｒｂ－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅは上記の「Ｒｂ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「Ｒｂ－Ｏ－ＣＯ－ＮＲｅ－で表される基」の具体例としては、メトキシカルボニルアミノ基などを挙げることができる。 In the “group represented by R b —O—CO—NR e —” for G, R b has the same meaning as in the above “group represented by R b —O—CO—”. R e has the same meaning as in the above “group represented by R b —CO—NR e —”.
Specific examples of the “group represented by R b —O—CO—NR e —” include a methoxycarbonylamino group.
　Ｇにおける「ＲｃＲｄＮ－ＣＯ－Ｏ－で表される基」中、ＲｃおよびＲｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。
　「ＲｃＲｄＮ－ＣＯ－Ｏ－で表される基」の具体例としては、カルバモイルオキシ基、Ｎ，Ｎ－ジメチルアミノカルボニルオキシ基などを挙げることができる。 In the “group represented by R c R d N—CO—O—” for G, R c and R d have the same meanings as those in the above “group represented by R c R d N—” .
Specific examples of the “group represented by R c R d N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.
　Ｇにおける「ＲｃＲｄＮ－ＣＯ－ＮＲｅ－で表される基」中、ＲｃおよびＲｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。Ｒｅは上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「ＲｃＲｄＮ－ＣＯ－ＮＲｅ－で表される基」の具体例としては、カルバモイルアミノ基、Ｎ，Ｎ－ジメチルアミノカルボニルアミノ基などを挙げることができる。 In the “group represented by R c R d N—CO—NR e —” for G, R c and R d have the same meanings as those in the above “group represented by R c R d N—” show. R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Specific examples of the “group represented by R c R d N—CO—NR e —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.
　Ｇにおける「ＲｃＲｄＮ－ＣＯ－ＣＯ－ＮＲｅ－で表される基」中、ＲｃおよびＲｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。Ｒｅは上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「ＲｃＲｄＮ－ＣＯ－ＣＯ－ＮＲｅ－で表される基」の具体例としては、２－（メチルアミノ）－２－オキソアセトアミド基、２－（ｔ－ブチルアミノ）－２－オキソアセトアミド基などを挙げることができる。 In the “group represented by R c R d N—CO—CO—NR e —” for G, R c and R d are the same as those in the above “group represented by R c R d N—” indicate meaning. R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Specific examples of the "group represented by R c R d N-CO-CO-NR e -" include 2-(methylamino)-2-oxoacetamide group, 2-(t-butylamino)-2- An oxoacetamide group and the like can be mentioned.
　Ｇにおける「Ｒａ－ＣＳ－ＮＲｅ－で表される基」中、Ｒａは上記の「Ｒａ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅは、上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ－ＣＳ－ＮＲｅ－で表される基」の具体例としては、エタンチオアミド基、プロパンチオアミド基、２－メチルプロパンチオアミド基などを挙げることができる。 In the "group represented by R a -CS-NR e -" for G, R a has the same meaning as in the above "group represented by R a -CO-". R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Specific examples of the "group represented by R a -CS-NR e -" include an ethanethioamide group, a propanethioamide group, a 2-methylpropanethioamide group and the like.
　Ｇにおける「ＲｃＲｄＮ－ＣＳ－ＮＲｅ－で表される基」中、ＲｃおよびＲｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。Ｒｅは上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「ＲｃＲｄＮ－ＣＳ－ＮＲｅ－で表される基」の具体例としては、３，３－ジメチルチオウレイド基などを挙げることができる。 In the "group represented by RcRdN -CS- NRe- " for G, Rc and Rd have the same meanings as those in the above "group represented by RcRdN- " . show. R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Specific examples of the “group represented by R c R d N—CS—NR e —” include a 3,3-dimethylthioureido group.
　Ｇにおける「ＲｂＳＯ２－ＮＲｅ－で表される基」中、Ｒｂは上記の「Ｒｂ－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅは上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　「ＲｂＳＯ２－ＮＲｅ－で表される基」の具体例としては、メタンスルホニルアミノ基などを挙げることができる。 In the “group represented by R b SO 2 —NR e —” for G, R b has the same meaning as in the above “group represented by R b —O—CO—”. R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Specific examples of the “group represented by R b SO 2 —NR e —” include a methanesulfonylamino group.
　Ｇにおける「ＲｃＲｄＮ－ＳＯ２－で表される基」中、ＲｃおよびＲｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。
　「ＲｃＲｄＮ－ＳＯ２－で表される基」の具体例としては、Ｎ，Ｎ－ジメチルアミノスルホニル基などを挙げることができる。 In the “group represented by R c R d N—SO 2 —” for G, R c and R d have the same meanings as those in the above “group represented by R c R d N—”.
Specific examples of the “group represented by R c R d N—SO 2 —” include an N,N-dimethylaminosulfonyl group.
　Ｇにおける「ＲａＯ－Ｎ＝ＣＲｆ－で表される基」中、Ｒａは上記の「Ｒａ－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　Ｒｆは、水素原子、アミノ基、または置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｒｆにおける置換基の具体例は、Ｒａにおいて例示したものと同じものを挙げることができる。
　「ＲａＯ－Ｎ＝ＣＲｆ－で表される基」の具体例としては、（ヒドロキシイミノ）メチル基、（エトキシイミノ）メチル基などを挙げることができる。 In the "group represented by R a ON=CR f -" for G, R a has the same meaning as in the above "group represented by R a -CO-".
R f represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent for R f are the same as those exemplified for Ra .
Specific examples of the "group represented by R a ON=CR f -" include (hydroxyimino)methyl group and (ethoxyimino)methyl group.
　Ｇにおける「Ｒａ－Ｃ（＝ＮＲｇ）－ＮＲｅ－で表される基」中、Ｒａは上記の「Ｒａ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅは上記の「Ｒａ－ＣＯ－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。
　Ｒｇは、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｇにおける置換基の具体例は、Ｒａにおいて例示したものと同じものを挙げることができる。 In the "group represented by R a -C(=NR g )-NR e -" for G, R a has the same meaning as in the above "group represented by R a -CO-". R e has the same meaning as in the above “group represented by R a —CO—NR e —”.
Each R g independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent for Rg are the same as those exemplified for Ra .
　Ｇにおける「ＲｃＲｄＮ－Ｃ（＝ＮＲｇ）－で表される基」中、ＲｃおよびＲｄは上記の「ＲｃＲｄＮ－で表される基」におけるそれらと同様の意味を示す。Ｒｇは上記の「Ｒａ－Ｃ（＝ＮＲｇ）－ＮＲｅ－で表される基」におけるそれと同様の意味を示す。 In the "group represented by R c R d NC(=NR g )-" for G, R c and R d are the same as those in the above "group represented by R c R d N-" indicate meaning. R g has the same meaning as in the above "group represented by R a -C(=NR g )-NR e -".
　Ｇにおける「ＲｈＲｉＳ（＝Ｏ）＝Ｎ－ＣＯ－で表される基」中、Ｒｈは、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示し、Ｒｉは、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　ＲｈまたはＲｉにおける置換基の具体例は、Ｒａにおいて例示したものと同じものを挙げることができる。 In the "group represented by R h R i S(=O)=N-CO-" for G, each R h is independently a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted represents a C6-10 aryl group, and each R i independently represents a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C6-10 aryl group;
Specific examples of substituents for R h or R i are the same as those exemplified for R a .
　ここで、ＲｈとＲｉは、一緒になって二価の有機基を形成してもよい。
　形成できる二価の有機基としては、置換若しくは無置換のＣ２～５アルキレン基または置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ２～５アルキレン基」としては、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ２～５アルキレン基」または「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；またはクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。 Here, R h and R i may together form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
　Ｇにおける「ＲｈＲｉＳ＝Ｎ－ＣＯ－で表される基」中、ＲｈまたはＲｉは上記の「ＲｈＲｉＳ（＝Ｏ）＝Ｎ－ＣＯ－で表される基」におけるそれらと同様の意味を示す。 In the "group represented by R h R i S=N--CO-" in G, R h or R i is the above "group represented by R h R i S(=O)=N--CO--" have similar meanings to those in
　Ｇにおける「ＲｈＲｊＣ＝Ｎ－Ｏ－で表される基」中、ＲｈおよびＲｊは上記の「ＲｈＲｊＳ＝Ｎ－Ｏ－で表される基」におけるそれと同様の意味を示す。
「ＲｈＲｊＣ＝Ｎ－Ｏ－で表される基」の具体例としては、（プロパン－２－イリデンアミノ）オキシ基などを挙げることができる。 In the "group represented by R h R j C=NO-" for G, R h and R j are the same as in the above "group represented by R h R j S=NO-" indicate meaning.
Specific examples of the “group represented by R h R j C═N—O—” include (propan-2-ylideneamino)oxy group and the like.
　置換基（Ｇ）が２以上ある場合に、そのうちの２つが一緒になって形成できる二価の有機基としては、置換若しくは無置換のＣ１～５アルキレン基、置換若しくは無置換のオキシＣ１～４アルキレン基、置換若しくは無置換のオキシＣ２～３アルキレンオキシ基、または置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ１～５アルキレン基」としては、メチレン基、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「オキシＣ１～４アルキレン基」としては、オキシメチレン基、オキシジメチレン基などを挙げることができる。
　「オキシＣ２～３アルキレンオキシ基」としては、オキシジメチレンオキシ基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ１～５アルキレン基」、「オキシＣ１～４アルキレン基」、「オキシＣ２～３アルキレンオキシ基」、「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；またはクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。 When there are two or more substituents (G), the divalent organic groups that can be formed by two of them together include a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxy C1-4 An alkylene group, a substituted or unsubstituted oxy C2-3 alkyleneoxy group, or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group can be mentioned.
Examples of the "C1-5 alkylene group" include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
Examples of the "oxy C1-4 alkylene group" include an oxymethylene group and an oxydimethylene group.
Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethylenoxy group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on the "C1-5 alkylene group", "oxy-C1-4 alkylene group", "oxy-C2-3 alkyleneoxy group" and "C1-3 alkyleneoxy C1-3 alkylene group" include a fluoro group, chloro Halogeno groups such as group, bromo group and iodo group; C1 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group and t-butyl group ~6 alkyl group; or C1~6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group and 1-fluoro-n-butyl group are preferred.
　本発明において、好ましいＧとしては、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換の３～１０員環のヘテロシクリル基、Ｒｂ－Ｏ－ＣＯ－で表される基、ＲｃＲｄＮ－で表される基、ＲｃＲｄＮ－ＣＯ－で表される基、Ｒａ－ＣＯ－Ｏ－で表される基、Ｒａ－ＣＯ－ＮＲｅ－で表される基、Ｒｂ－Ｏ－ＣＯ－ＮＲｅ－で表される基、ＲｃＲｄＮ－ＣＯ－Ｏ－で表される基、ＲｃＲｄＮ－ＣＯ－ＮＲｅ－で表される基、ＲｃＲｄＮ－ＣＳ－ＮＲｅ－で表される基、ＲｂＳＯ２－ＮＲｅ－で表される基、ＲａＯ－Ｎ＝ＣＲｆ－で表される基、またはＲｈＲｉＣ＝Ｎ－Ｏ－で表される基が挙げることができる。 In the present invention, preferred G is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted 3-10 a membered heterocyclyl group, a group represented by R b --O--CO--, a group represented by R c R d N--, a group represented by R c R d N -- CO--, and R a --CO-- A group represented by O—, a group represented by R a —CO—NR e —, a group represented by R b —O—CO—NR e —, a group represented by R c R d N—CO—O— a group represented by R c R d N—CO—NR e —, a group represented by R c R d N—CS—NR e —, a group represented by R b SO 2 —NR e — group, a group represented by R a ON=CR f -, or a group represented by R h R i C=NO-.
〔上記Ｘ３以外のＸ３及びＲＮ１、ＲＮ２〕
　さらに、Ｘ３は、ＲＮ１Ｏ－で表される基、ＲＮ１－ＣＯ－Ｏ－で表される基、ＲＮ１－Ｏ－ＣＯ－Ｏ－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－Ｏ－で表される基、ＲＮ１－ＣＳ－Ｏ－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＳ－Ｏ－で表される基、ＲＮ１ＲＮ２Ｎ－で表される基、ＲＮ１－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－ＣＯ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－Ｏ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－ＣＳ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＳ－ＮＲＮ２－で表される基、ＲＮ１ＳＯ２－ＮＲＮ２－で表される基、またはＲＮ１－Ｃ（＝ＮＲＮ１）－ＮＲＮ２－で表される基を示す。 [X 3 and R N1 and R N2 other than X 3 above]
Furthermore, X 3 is a group represented by R N1 O—, a group represented by R N1 —CO—O—, a group represented by R N1 —O—CO—O—, R N1 R N1 N— a group represented by CO--O--, a group represented by R N1 --CS--O--, a group represented by R N1 R N1 N--CS--O--, a group represented by R N1 R N2 N-- , a group represented by R N1 -CO-NR N2 -, a group represented by R N1 -CO-CO-NR N2 -, a group represented by R N1 -O-CO-NR N2 -, R N1 R A group represented by N1 N—CO—NR N2 —, a group represented by R N1 R N1 N—CO—CO—NR N2 —, a group represented by R N1 —CS—NR N2 —, R N1 R A group represented by N1 N--CS--NR N2 --, a group represented by R N1 SO 2 --NR N2 --, or a group represented by R N1 --C(=NR N1 )--NR N2 --.
　ＲＮ１、およびＲＮ２は、それぞれ独立に、水素原子、置換若しくは無置換の直鎖Ｃ１～６アルキル基、置換若しくは無置換の直鎖Ｃ２～６アルケニル基、置換若しくは無置換の直鎖Ｃ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の４～６員環のヘテロシクリル基を示し、ここで、ＲＮ１とＲＮ１、またはＲＮ１とＲＮ２は、一緒になって二価の有機基を形成してもよい。 R N1 and R N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R N1 and R N1 , or R N1 and R N2 may together form a divalent organic group.
　ＲＮ１、およびＲＮ２における「直鎖Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基を挙げることができる。
　ＲＮ１、およびＲＮ２における「直鎖Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－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－ヘキセニル基を挙げることができる。
　ＲＮ１、およびＲＮ２における「直鎖Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－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－ヘキシニル基などを挙げることができる。
　ＲＮ１、およびＲＮ２における「４員環のヘテロシクリル基」しては、アゼチジニル基、オキセタニル基を挙げることができる。
　ＲＮ１、およびＲＮ２におけるその他の置換基の具体例は、Ｘ１において例示したものと同じものを挙げることができる。 Examples of the "linear C1-6 alkyl group" for R N1 and R N2 include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group and n-hexyl group.
The "linear C2-6 alkenyl group" for R N1 and R N2 includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl and 5-hexenyl groups.
The "linear C2-6 alkynyl group" for R N1 and R N2 includes an ethynyl group, 1-propynyl group, 2-propynyl 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 and the like.
Examples of the "4-membered heterocyclyl group" for R N1 and R N2 include an azetidinyl group and an oxetanyl group.
Specific examples of other substituents for R N1 and R N2 are the same as those exemplified for X 1 .
　〔Ｂ〕
　Ｂは、単結合、酸素原子、硫黄原子、スルフィニル基、スルホニル基、または－ＮＲＮ３－で表される基を示し、ＲＮ３は、水素原子、置換若しくは無置換のＣ１～６アルキル基、ホルミル基、または置換若しくは無置換のＣ１～６アルキルカルボニル基を示す。 [B]
B is a single bond, an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR N3 -, where R N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, formyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group.
　ＲＮ３における「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。ＲＮ３における「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。
　ＲＮ３における「Ｃ１～６アルキルカルボニル基」としては、アセチル基、プロピオニル基、ブチリル基、ｉ－プロピルカルボニル基などを挙げることができる。 The “C1-6 alkyl group” in R N3 may be linear or branched. The "C1-6 alkyl group" in R N3 includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Examples of the “C1-6 alkylcarbonyl group” for R N3 include an acetyl group, a propionyl group, a butyryl group, an i-propylcarbonyl group and the like.
　ＲＮ３における「Ｃ１～６アルキル基」、および「Ｃ１～６アルキルカルボニル」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；（エチリデンアミノ）オキシ基、プロパン－２－イリデンアミノ）オキシ基などの（Ｃ１～６アルキリデンアミノ）オキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；またはシアノ基が好ましい。 The substituents on the "C1-6 alkyl group" and "C1-6 alkylcarbonyl" in R N3 include a fluoro group, a chloro group, a bromo group, a halogeno group such as an iodo group; a hydroxyl group; a methoxy group, an ethoxy group, C1-6 alkoxy groups such as n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy group, 2,3- C1-6 haloalkoxy groups such as dichlorobutoxy group and trifluoromethoxy group; (C1-6 alkylideneamino)oxy groups such as (ethylideneamino)oxy group and propane-2-ylideneamino)oxy group; cyclopropyl group and cyclobutyl group , cyclopentyl group, C3-6 cycloalkyl group such as cyclohexyl group; phenyl group, C6-10 aryl group such as naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethyl any one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group such as a phenyl group and a 4-trifluoromethoxyphenyl group; 5-membered substituted C6-10 aryl group; pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. ring heteroaryl group; a 5-membered ring substituted with one or more substituents selected from a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group heteroaryl group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered heteroaryl group such as triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or A 6-membered heteroaryl group substituted with one or more substituents selected from C1-6 haloalkoxy groups; or a cyano group is preferred.
　〔Ａ〕
　Ａは、置換若しくは無置換のＣ１～６アルキレン基、置換若しくは無置換のＣ２～６アルケニレン基、置換若しくは無置換のＣ２～６アルキニレン基、または置換若しくは無置換のＣ３～６シクロアルキレン基を示す。 [A]
A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group .
　Ａにおける「Ｃ１～６アルキレン基」としては、メチレン基、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　Ａにおける「Ｃ２～６アルケニレン基」としては、ビニレン基（－ＣＨ＝ＣＨ－）、ジビニレン基（－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－）、プロペニレン基（－ＣＨ＝ＣＨ－ＣＨ２－、－ＣＨ２－ＣＨ＝ＣＨ－）などを挙げることができる。
　Ａにおける「Ｃ２～６アルキニレン基」としては、エチニレン基（－Ｃ≡Ｃ－）、プロピニレン基（－ＣＨ２－Ｃ≡Ｃ－、－Ｃ≡Ｃ－ＣＨ２－）、などを挙げることができる。
　Ａにおける「Ｃ３～６シクロアルキレン基」としては、１，２－シクロプロピレン基、１，２－シクロブタンジイル基、１，３－シクロブタンジイル基などを挙げることができる。 Examples of the "C1-6 alkylene group" for A include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
The "C2-6 alkenylene group" in A includes a vinylene group (-CH=CH-), a divinylene group (-CH=CH-CH=CH-), a propenylene group (-CH=CH-CH 2 -, -CH 2 -CH=CH-) and the like.
Examples of the "C2-6 alkynylene group" for A include an ethynylene group (-C≡C-), a propynylene group (-CH 2 -C≡C-, -C≡C-CH 2 -), and the like. .
Examples of the "C3-6 cycloalkylene group" for A include 1,2-cyclopropylene group, 1,2-cyclobutanediyl group, 1,3-cyclobutanediyl group and the like.
　本発明において、好ましいＡとしては、置換若しくは無置換のＣ１～６アルキレン基または置換若しくは無置換のＣ２～６アルケニレン基を挙げることができる。
さらに好ましいＡとしては、置換若しくは無置換のＣ２アルキレン基（ジメチレン基）または置換若しくは無置換のＣ２アルケニレン基（ビニレン基）を挙げることができる。
　Ｃ１～６アルキレン基またはＣ２～６アルケニレン基上の置換基としては、以下の置換基群より選択される１または２以上の置換基を挙げることができる（以下、この置換基を記号「Ｇａ」で表すことがある。）。
　また、置換基（Ｇａ）は２以上ある場合、そのうちの２つが一緒になって二価の有機基を形成してもよい。以下に置換基群を示す。
　ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、メルカプト基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の３～６員環のヘテロシクリル基、置換若しくは無置換の３～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒａ１－ＣＯ－で表される基、カルボキシ基、Ｒｂ１－Ｏ－ＣＯ－で表される基、Ｒｃ１Ｒｄ１Ｎ－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－で表される基、Ｒａ１－ＣＯ－Ｏ－で表される基、Ｒａ１－ＣＯ－ＮＲｅ１－で表される基、Ｒｂ１－Ｏ－ＣＯ－Ｏ－で表される基、Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－Ｏ－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－ＮＲｅ１－で表される基、Ｒｂ１ＳＯ２－ＮＲｅ１－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＳＯ２－で表される基、Ｒａ１Ｏ－Ｎ＝ＣＲｆ１－で表される基、Ｒｇ１Ｒｈ１Ｃ＝Ｎ－Ｏ－で表される基、オキソ基（Ｏ＝）、チオキソ基（Ｓ＝）、Ｒａ１－Ｎ＝で表される二価の基、Ｒａ１Ｏ－Ｎ＝で表される二価の基、Ｒｃ１Ｒｄ１Ｎ－Ｎ＝で表される二価の基、Ｒａ１－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基、Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基、Ｒｂ１ＳＯ２－ＮＲｅ１－Ｎ＝で表される二価の基。 In the present invention, A is preferably a substituted or unsubstituted C1-6 alkylene group or a substituted or unsubstituted C2-6 alkenylene group.
More preferred examples of A include a substituted or unsubstituted C2 alkylene group (dimethylene group) and a substituted or unsubstituted C2 alkenylene group (vinylene group).
Examples of substituents on the C1-6 alkylene group or C2-6 alkenylene group include one or more substituents selected from the following group of substituents (hereinafter, this substituent is denoted by the symbol "Ga" can be expressed as ).
Moreover, when there are two or more substituents (Ga), two of them may combine to form a divalent organic group. Substituent groups are shown below.
halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, mercapto group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted Or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3 to 6-membered heterocyclyl group, substituted or unsubstituted 3- to 6-membered heterocyclyloxy group, nitro group, cyano group, group represented by R a1 —CO—, carboxy group, R b1 —O—CO— a group represented by R c1 R d1 N—, a group represented by R c1 R d1 N—CO—, a group represented by R a1 —CO—O—, R a1 —CO— a group represented by NR e1 —, a group represented by R b1 —O—CO—O—, a group represented by R b1 —O—CO—NR e1 —, R c1 R d1 N—CO—O— a group represented by R c1 R d1 N—CO—NR e1 — a group represented by R b1 SO 2 —NR e1 — a group represented by R c1 R d1 N—SO 2 — group, R a1 ON =CR f1 - group, R g1 R h1 C=NO- group, oxo group (O=), thioxo group (S=), R a1 - a divalent group represented by N=, a divalent group represented by R a1 ON =, a divalent group represented by R c1 R d1 NN=, R a1 -CO-NR e1 -N=, a divalent group represented by R b1 -O-CO-NR e1 -N=, a divalent group represented by R b1 SO 2 -NR e1 -N= Base.
　上記の置換基群中、Ｒａ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｂ１は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｃ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｄ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示し、ここで、Ｒｃ１とＲｄ１は、一緒になって二価の有機基を形成してもよい。
　Ｒｅ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒｆ１は、水素原子、または置換若しくは無置換のＣ１～６アルキル基を示し、
　Ｒｇ１は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｈ１は、水素原子、または置換若しくは無置換のＣ１～６アルキル基を示し、ここで、Ｒｇ１とＲｈ１は、一緒になって二価の有機基を形成してもよい。 In the above substituent groups, each R a1 is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R b1 each independently represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
Each R c1 is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
Each R d1 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group, wherein R c1 and R d1 are together A divalent organic group may be formed.
R e1 each independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
R f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
R g1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, substituted or an unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
R h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, wherein R g1 and R h1 may together form a divalent organic group.
　Ｇａにおける「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。 Examples of the "halogeno group" in Ga include a fluoro group, a chloro group, a bromo group, an iodine group, and the like.
　Ｇａにおける「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。Ｇａにおける「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。 The "C1-6 alkyl group" in Ga may be linear or branched. The "C1-6 alkyl group" in Ga includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s- Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
　Ｇａにおける「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などを挙げることができる。 The "C2-6 alkenyl group" in Ga includes a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group , 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
　Ｇａにおける「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などを挙げることができる。 The "C2-6 alkynyl group" in Ga includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group , 1,1-dimethyl-2-butynyl group, and the like.
　Ｇａにおける「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、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、ｉ－ヘキシルオキシ基などを挙げることができる。
　Ｇａにおける「Ｃ２～６アルケニルオキシ基」としては、ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などを挙げることができる。
　Ｇａにおける「Ｃ２～６アルキニルオキシ基」としては、エチニルオキシ基、プロパルギルオキシ基などを挙げることができる。 The "C1-6 alkoxy group" for Ga includes a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group, Examples include s-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of the "C2-6 alkenyloxy group" for Ga include a vinyloxy group, an allyloxy group, a propenyloxy group, and a butenyloxy group.
Examples of the "C2-6 alkynyloxy group" for Ga include an ethynyloxy group and a propargyloxy group.
　Ｇａにおける「Ｃ１～６アルキルチオ基」としては、メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｎ－ブチルチオ基、ｎ－ペンチルチオ基、ｎ－ヘキシルチオ基、ｉ－プロピルチオ基などを挙げることができる。
　Ｇａにおける「Ｃ１～６アルキルスルフィニル基」としては、メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などを挙げることができる。
　Ｇａにおける「Ｃ１～６アルキルスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などを挙げることができる。 Examples of the "C1-6 alkylthio group" for Ga include methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, i-propylthio and the like.
Examples of the "C1-6 alkylsulfinyl group" in Ga include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
Examples of the "C1-6 alkylsulfonyl group" for Ga include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.
　Ｇａにおける「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」、「Ｃ１～６アルコキシ基」、「Ｃ２～６アルケニルオキシ基」、「Ｃ２～６アルキニルオキシ基」、「Ｃ１～６アルキルチオ基」、「Ｃ１～６アルキルスルフィニル基」、または「Ｃ１～６アルキルスルホニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；またはシアノ基が好ましい。 Ga "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkynyloxy group ”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” or “C1-6 alkylsulfonyl group” include halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group. hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phenyl group, C6-10 aryl group such as naphthyl group; C1-6 alkyl group such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group , a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, a C6-10 aryl group substituted with one or more substituents; or a cyano group.
　Ｇａにおける「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｇａにおける「Ｃ３～６シクロアルキルオキシ基」としては、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などを挙げることができる。 Examples of the "C3-6 cycloalkyl group" for Ga include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
Examples of the "C3-6 cycloalkyloxy group" for Ga include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
　Ｇａにおける「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インデニル基、インダニル基、テトラリニル基などを挙げることができる。
　Ｇａにおける「Ｃ６～１０アリールオキシ基」としては、フェノキシ基、ナフトキシ基などを挙げることができる。 Examples of the "C6-10 aryl group" for Ga include a phenyl group, naphthyl group, indenyl group, indanyl group, tetralinyl group and the like.
Examples of the "C6-10 aryloxy group" in Ga include a phenoxy group and a naphthoxy group.
　Ｇａにおける「Ｃ６～１０アリールチオ基」としては、フェニルチオ基、ナフチルチオ基などを挙げることができる。
　Ｇａにおける「Ｃ６～１０アリールスルフィニル基」としては、フェニルスルフィニル基、ナフチルスルフィニル基などを挙げることができる。
　Ｇａにおける「Ｃ６～１０アリールスルホニル基」としては、フェニルスルホニル基、ナフチルスルホニル基などを挙げることができる。 Examples of the "C6-10 arylthio group" in Ga include a phenylthio group and a naphthylthio group.
Examples of the "C6-10 arylsulfinyl group" for Ga include a phenylsulfinyl group and a naphthylsulfinyl group.
Examples of the “C6-10 arylsulfonyl group” for Ga include a phenylsulfonyl group and a naphthylsulfonyl group.
　Ｇａにおける「３～６員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１、２、３または４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。「３～６員環のヘテロシクリル基」としては、３～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。 The "3- to 6-membered heterocyclyl group" for Ga is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. . When there are two or more heteroatoms, they may be the same or different. The "3- to 6-membered heterocyclyl group" includes a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
　３～６員環の飽和ヘテロシクリル基としては、アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～６員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基を挙げることができる。
　５～６員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基を挙げることができる。 3- to 6-membered saturated heterocyclyl groups include aziridinyl, epoxy, azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, Dioxolanyl group, dioxanyl group and the like can be mentioned.
Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.
　Ｇａにおける「３～６員環のヘテロシクリルオキシ基」は、３～６員環のヘテロシクリル基とオキシ基が結合した構造を有する。具体例としては、チアゾリルオキシ基、ピリジルオキシ基などを挙げることができる。 The "3- to 6-membered heterocyclyloxy group" in Ga has a structure in which a 3- to 6-membered heterocyclyl group and an oxy group are bonded. Specific examples include a thiazolyloxy group and a pyridyloxy group.
　Ｇａにおける「Ｃ３～６シクロアルキル基」、「Ｃ３～６シクロアルキルオキシ基」、「Ｃ６～１０アリール基」、「Ｃ６～１０アリールオキシ基」、「Ｃ６～１０アリールチオ基」、「Ｃ６～１０アリールスルフィニル基」、「Ｃ６～１０アリールスルホニル基」、「３～６員環のヘテロシクリル基」、または「３～６員環のヘテロシクリルオキシ基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；またはシアノ基が好ましい。 Ga "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10 Arylsulfinyl group", "C6-10 arylsulfonyl group", "3- to 6-membered heterocyclyl group" or "3- to 6-membered heterocyclyloxy group" include a fluoro group, a chloro group, halogeno groups such as bromo group and iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group , C1-6 alkyl groups such as n-hexyl group; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy group such as t-butoxy group; 2-chloro -C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group and 4-methoxyphenyl a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 A C6-10 aryl group substituted with any one or more substituents of a haloalkoxy group; or a cyano group is preferred.
　Ｇａにおける「Ｒａ１－ＣＯ－で表される基」中、Ｒａ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。 In the "group represented by R a1 -CO-" for Ga, R a1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted It represents a C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group.
　Ｒａ１における「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。
　Ｒａ１における「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基などを挙げることができる。
　Ｒａ１における「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基などを挙げることができる。
　Ｒａ１における「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、または「Ｃ２～６アルキニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；またはシアノ基が好ましい。 The "C1-6 alkyl group" for R a1 includes a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s -butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like.
Examples of the “C2-6 alkenyl group” for R a1 include a vinyl group and a 1-propenyl group.
Examples of the “C2-6 alkynyl group” for R a1 include an ethynyl group and a 1-propynyl group.
Examples of substituents on the "C1-6 alkyl group", "C2-6 alkenyl group", or "C2-6 alkynyl group" in R a1 include halogeno groups such as fluoro, chloro, bromo, and iodo groups; hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, t-butoxy; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group; phenyl group, naphthyl a C6-10 aryl group such as a group; a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group such as a 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group; or a C6-10 aryl group substituted with one or more substituents; or a cyano group.
　Ｒａ１における「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｒａ１における「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基などを挙げることができる。 Examples of the “C3-6 cycloalkyl group” for R a1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
Examples of the “C6-10 aryl group” for R a1 include a phenyl group and a naphthyl group.
　Ｒａ１における「５～６員環のヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる１、２、３または４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。「５～６員環のヘテロシクリル基」としては、５～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。
　５～６員環の飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～６員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基を挙げることができる。
　５～６員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基を挙げることができる。 The “5- to 6-membered heterocyclyl group” for R a1 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. be. When there are two or more heteroatoms, they may be the same or different. Examples of the "5- to 6-membered heterocyclyl group" include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .
Examples of 5- to 6-membered saturated heterocyclyl groups include pyrrolidinyl, tetrahydrofuranyl, thiazolidinyl, tetrahydro-2H-pyranyl, piperidyl, piperazinyl, morpholinyl, dioxolanyl and dioxanyl groups.
Examples of 5- to 6-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. and 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group.
Examples of 5- to 6-membered partially unsaturated heterocyclyl groups include pyrrolinyl, dihydrofuranyl, imidazolinyl, pyrazolinyl, oxazolinyl, isoxazolinyl, and other 5-membered partially unsaturated heterocyclyl groups; dihydro Six-membered partially unsaturated heterocyclyl groups such as pyranyl groups can be mentioned.
　Ｒａ１における「Ｃ３～６シクロアルキル基」、「Ｃ６～１０アリール基」、または「５～６員環のヘテロシクリル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、またはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；またはシアノ基が好ましい。 Examples of substituents on the "C3-6 cycloalkyl group", "C6-10 aryl group", or "5- to 6-membered heterocyclyl group" for R a1 include a fluoro group, a chloro group, a bromo group, an iodo group, and the like. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. C1 ~ 6 alkyl group of; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, C1 ~ 6 haloalkyl group such as 1-fluoro-n-butyl group; hydroxyl group; methoxy group , ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, C1-6 alkoxy groups such as t-butoxy group; 2-chloro-n-propoxy group, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group and trifluoromethoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group and 4-chlorophenyl group , 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc., a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group C6-10 aryl groups substituted with one or more substituents; or cyano groups are preferred.
　「Ｒａ１－ＣＯ－で表される基」の具体例としては、ホルミル基、アセチル基などを挙げることができる。 Specific examples of the "group represented by R a1 -CO-" include a formyl group and an acetyl group.
　Ｇａにおける「Ｒｂ１－Ｏ－ＣＯ－で表される基」中、Ｒｂ１は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒｂ１における置換基の具体例は、Ｒａ１において例示したものと同じものを挙げることができる。 In the "group represented by R b1 -O-CO-" for Ga, R b1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ~6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group.
Specific examples of the substituent for R b1 are the same as those exemplified for R a1 .
　「Ｒｂ１－Ｏ－ＣＯ－で表される基」の具体例としては、メトキシカルボニル基、エトキシカルボニル基、ｔ－ブトキシカルボニル基などを挙げることができる。 Specific examples of the "group represented by R b1 -O-CO-" include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group and the like.
　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－で表される基」中、Ｒｃ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、Ｒｄ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｃ１またはＲｄ１における置換基の具体例は、Ｒａ１において例示したものと同じものを挙げることができる。
　ここで、Ｒｃ１とＲｄ１は、一緒になって二価の有機基を形成してもよい。
形成できる二価の有機基としては、置換若しくは無置換のＣ２～５アルキレン基または置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ２～５アルキレン基」としては、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ２～５アルキレン基」または「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；またはクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。 In the "group represented by R c1 R d1 N-" for Ga, R c1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted A C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, and R d1 is , a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent for R c1 or R d1 are the same as those exemplified for R a1 .
Here, R c1 and R d1 may together form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Examples of substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl, ethyl, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
　「Ｒｃ１Ｒｄ１Ｎ－で表される基」の具体例としては、アミノ基、メチルアミノ基、ジメチルアミノ基などを挙げることができる。 Specific examples of the "group represented by R c1 R d1 N-" include an amino group, a methylamino group and a dimethylamino group.
　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－で表される基」中、Ｒｃ１およびＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－で表される基」の具体例としては、カルバモイル基、Ｎ，Ｎ－ジメチルアミノカルボニル基、Ｎ－（ｉ－プロピル）アミノカルボニル基、Ｎ－（ｉ－プロピル）－Ｎ－メチルアミノカルボニル基などを挙げることができる。 In the “group represented by R c1 R d1 N—CO—” for Ga, R c1 and R d1 have the same meanings as those in the above “group represented by R c1 R d1 N—”.
Specific examples of the “group represented by R c1 R d1 N—CO—” include a carbamoyl group, an N,N-dimethylaminocarbonyl group, an N-(i-propyl)aminocarbonyl group, and an N-(i-propyl )—N-methylaminocarbonyl group and the like.
　Ｇａにおける「Ｒａ１－ＣＯ－Ｏ－で表される基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ１－ＣＯ－Ｏ－で表される基」の具体例としては、アセチルオキシ基などを挙げることができる。 In the "group represented by R a1 -CO-O-" for Ga, R a1 has the same meaning as in the above "group represented by R a1 -CO-".
Specific examples of the "group represented by R a1 -CO-O-" include an acetyloxy group.
　Ｇａにおける「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　Ｒｅ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｅ１における置換基の具体例は、Ｒａ１において例示したものと同じものを挙げることができる。
　「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」の具体例としては、アセチルアミノ基などを挙げることができる。 In the "group represented by R a1 -CO-NR e1 -" for Ga, R a1 has the same meaning as in the above "group represented by R a1 -CO-".
R e1 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent for R e1 are the same as those exemplified for R a1 .
Specific examples of the "group represented by R a1 -CO-NR e1 -" include an acetylamino group.
　Ｇａにおける「Ｒｂ１－Ｏ－ＣＯ－Ｏ－で表される基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒｂ１－Ｏ－ＣＯ－Ｏ－で表される基」の具体例としては、メトキシカルボニルオキシ基、エトキシカルボニルオキシ基などを挙げることができる。 In the “group represented by R b1 —O—CO—O—” for Ga, R b1 has the same meaning as in the above “group represented by R b1 —O—CO—”.
Specific examples of the "group represented by R b1 -O-CO-O-" include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.
　Ｇａにおける「Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－で表される基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒｂ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。
　「Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－で表される基」の具体例としては、メトキシカルボニルアミノ基などを挙げることができる。 In the “group represented by R b1 —O—CO—NR e1 —” for Ga, R b1 has the same meaning as in the above “group represented by R b1 —O—CO—”. R e1 has the same meaning as in the above “group represented by R b1 —CO—NR e1 —”.
Specific examples of the “group represented by R b1 —O—CO—NR e1 —” include a methoxycarbonylamino group.
　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－Ｏ－で表される基」中、Ｒｃ１およびＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－Ｏ－で表される基」の具体例としては、カルバモイルオキシ基、Ｎ，Ｎ－ジメチルアミノカルボニルオキシ基などを挙げることができる。 In the “group represented by R c1 R d1 N—CO—O—” for Ga, R c1 and R d1 have the same meanings as those in the above “group represented by R c1 R d1 N—” .
Specific examples of the “group represented by R c1 R d1 N—CO—O—” include a carbamoyloxy group and an N,N-dimethylaminocarbonyloxy group.
　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－ＮＲｅ１－で表される基」中、Ｒｃ１およびＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－ＮＲｅ１－で表される基」の具体例としては、カルバモイルアミノ基、Ｎ，Ｎ－ジメチルアミノカルボニルアミノ基などを挙げることができる。 In the "group represented by R c1 R d1 N-CO-NR e1 -" for Ga, R c1 and R d1 have the same meanings as those in the above "group represented by R c1 R d1 N-". show. R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
Specific examples of the “group represented by R c1 R d1 N—CO—NR e1 —” include a carbamoylamino group and an N,N-dimethylaminocarbonylamino group.
　Ｇａにおける「Ｒｂ１ＳＯ２－ＮＲｅ１－で表される基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。
　「Ｒｂ１ＳＯ２－ＮＲｅ１－で表される基」の具体例としては、メタンスルホニルアミノ基などを挙げることができる。 In the “group represented by R b1 SO 2 —NR e1 —” for Ga, R b1 has the same meaning as in the above “group represented by R b1 —O—CO—”. R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
Specific examples of the “group represented by R b1 SO 2 —NR e1 —” include a methanesulfonylamino group and the like.
　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－ＳＯ２－で表される基」中、Ｒｃ１およびＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－ＳＯ２－で表される基」の具体例としては、Ｎ，Ｎ－ジメチルアミノスルホニル基などを挙げることができる。 In the “group represented by R c1 R d1 N—SO 2 —” for Ga, R c1 and R d1 have the same meanings as those in the above “group represented by R c1 R d1 N—”.
Specific examples of the “group represented by R c1 R d1 N—SO 2 —” include an N,N-dimethylaminosulfonyl group.
　Ｇａにおける「Ｒａ１Ｏ－Ｎ＝ＣＲｆ１－で表される基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　Ｒｆ１は、水素原子、または置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｒｆ１における置換基の具体例は、Ｒａにおいて例示したものと同じものを挙げることができる。
　「Ｒａ１Ｏ－Ｎ＝ＣＲｆ１－で表される基」の具体例としては、（ヒドロキシイミノ）メチル基、（エトキシイミノ）メチル基などを挙げることができる。 In the "group represented by R a1 ON=CR f1 -" for Ga, R a1 has the same meaning as in the above "group represented by R a1 -CO-".
R f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent for R f1 are the same as those exemplified for Ra .
Specific examples of the "group represented by R a1 ON =CR f1 -" include (hydroxyimino)methyl group and (ethoxyimino)methyl group.
　Ｇａにおける「Ｒｇ１Ｒｈ１Ｃ＝Ｎ－Ｏ－で表される基」中、Ｒｇ１は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、Ｒｈ１は、水素原子、または置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｒｇ１またはＲｈ１における置換基の具体例は、Ｒａ１において例示したものと同じものを挙げることができる。
　ここで、Ｒｇ１とＲｈ１は、一緒になって二価の有機基を形成してもよい。
　形成できる二価の有機基としては、置換若しくは無置換のＣ２～５アルキレン基または置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ２～５アルキレン基」としては、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ２～５アルキレン基」または「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；またはクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。
　「Ｒｇ１Ｒｈ１Ｃ＝Ｎ－Ｏ－で表される基」の具体例としては、（プロパン－２－イリデンアミノ）オキシ基などを挙げることができる。 In the "group represented by R g1 R h1 C=NO-" for Ga, R g1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted represents a substituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group, R h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent for R g1 or R h1 are the same as those exemplified for R a1 .
Here, R g1 and R h1 may together form a divalent organic group.
Divalent organic groups that can be formed include substituted or unsubstituted C2-5 alkylene groups or substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene groups.
Examples of the "C2-5 alkylene group" include a dimethylene group, a trimethylene group, a tetramethylene group and the like.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on the "C2-5 alkylene group" or "C1-3 alkyleneoxy C1-3 alkylene group" include halogeno groups such as fluoro, chloro, bromo, and iodo groups; methyl group, ethyl group, n - C1-6 alkyl groups such as propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group; or chloromethyl group, chloroethyl group, trifluoromethyl group, 1 , 2-dichloro-n-propyl group, 1-fluoro-n-butyl group and other C1-6 haloalkyl groups are preferred.
Specific examples of the "group represented by R g1 R h1 C=NO-" include a (propan-2-ylideneamino)oxy group.
　Ｇａにおける「Ｒａ１－Ｎ＝で表される二価の基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ１－Ｎ＝で表される二価の基」の具体例としては、イミノ基（ＨＮ＝）、メチルイミノ基などを挙げることができる。 In the "divalent group represented by R a1 -N=" for Ga, R a1 has the same meaning as in the above "group represented by R a1 -CO-".
Specific examples of the "divalent group represented by R a1 -N=" include an imino group (HN=) and a methylimino group.
　Ｇａにおける「Ｒａ１Ｏ－Ｎ＝で表される二価の基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ１Ｏ－Ｎ＝で表される二価の基」の具体例としては、Ｎ－ヒドロキシイミノ基、Ｎ－メトキシイミノ基などを挙げることができる。 In the "divalent group represented by R a1 ON=" for Ga, R a1 has the same meaning as in the above "group represented by R a1 -CO-".
Specific examples of the "divalent group represented by R a1 ON =" include an N-hydroxyimino group and an N-methoxyimino group.
　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－Ｎ＝で表される二価の基」中、Ｒｃ１およびＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－Ｎ＝で表される二価の基」の具体例としては、２，２－ジメチルヒドラジニリデン基などを挙げることができる。 In the "divalent group represented by R c1 R d1 NN=" for Ga, R c1 and R d1 have the same meanings as those in the above "group represented by R c1 R d1 N-". show.
Specific examples of the “divalent group represented by R c1 R d1 N—N=” include a 2,2-dimethylhydrazinylidene group.
　Ｇａにおける「Ｒａ１－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。 In the "divalent group represented by R a1 -CO-NR e1 -N=" in Ga, R a1 has the same meaning as in the above "group represented by R a1 -CO-". R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
　Ｇａにおける「Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。 In the “divalent group represented by R b1 —O—CO—NR e1 —N=” in Ga, R b1 has the same meaning as in the above “group represented by R b1 —O—CO—” indicate. R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
　Ｇａにおける「Ｒｂ１ＳＯ２－ＮＲｅ１－Ｎ＝で表される二価の基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。 In the “divalent group represented by R b1 SO 2 —NR e1 —N=” in Ga, R b1 has the same meaning as in the above “group represented by R b1 —O—CO—” . R e1 has the same meaning as in the above “group represented by R a1 —CO—NR e1 —”.
　置換基（Ｇａ）が２以上ある場合に、そのうちの２つが一緒になって形成できる二価の有機基としては、置換若しくは無置換のＣ１～５アルキレン基、置換若しくは無置換のオキシＣ１～４アルキレン基、置換若しくは無置換のオキシＣ２～３アルキレンオキシ基、または置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ１～５アルキレン基」としては、メチレン基、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「オキシＣ１～４アルキレン基」としては、オキシメチレン基、オキシジメチレン基などを挙げることができる。
　「オキシＣ２～３アルキレンオキシ基」としては、オキシジメチレンオキシ基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ１～５アルキレン基」、「オキシＣ１～４アルキレン基」、「オキシＣ２～３アルキレンオキシ基」、「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；またはクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。 When there are two or more substituents (Ga), the divalent organic group that can be formed by two of them together includes a substituted or unsubstituted C1-5 alkylene group, a substituted or unsubstituted oxy C1-4 An alkylene group, a substituted or unsubstituted oxy C2-3 alkyleneoxy group, or a substituted or unsubstituted C1-3 alkyleneoxy C1-3 alkylene group can be mentioned.
Examples of the "C1-5 alkylene group" include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
Examples of the "oxy C1-4 alkylene group" include an oxymethylene group and an oxydimethylene group.
Examples of the "oxy C2-3 alkyleneoxy group" include an oxydimethylenoxy group.
Examples of the "C1-3 alkyleneoxy C1-3 alkylene group" include a dimethyleneoxydimethylene group and the like.
Substituents on the "C1-5 alkylene group", "oxy-C1-4 alkylene group", "oxy-C2-3 alkyleneoxy group" and "C1-3 alkyleneoxy C1-3 alkylene group" include a fluoro group, chloro Halogeno groups such as group, bromo group and iodo group; C1 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group and t-butyl group ~6 alkyl group; or C1~6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group and 1-fluoro-n-butyl group are preferred.
　本発明において、好ましいＧａとしては、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、Ｒａ１－ＣＯ－Ｏ－で表される基、オキソ基（Ｏ＝）、またはＲａ１Ｏ－Ｎ＝で表される二価の基を挙げることができる。
　この場合、好ましい置換若しくは無置換の５～６員環のヘテロシクリルオキシ基としては、テトラヒドロ－２Ｈ－ピラン－４－イル基を挙げることができる。 In the present invention, preferred Ga includes a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a substituted or unsubstituted C3 ~ 6 cycloalkyloxy group, substituted or unsubstituted C6 ~ 10 aryloxy group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, a group represented by R a1 -CO-O-, oxo A group (O=) or a divalent group represented by R a1 ON = can be mentioned.
In this case, a preferred substituted or unsubstituted 5- to 6-membered heterocyclyloxy group is a tetrahydro-2H-pyran-4-yl group.
　本発明において、さらに好ましいＧａとしては、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、Ｒａ１－ＣＯ－Ｏ－で表される基、オキソ基（Ｏ＝）、またはＲａ１Ｏ－Ｎ＝で表される二価の基を挙げることができる。 In the present invention, more preferred Ga includes a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, R a1 - A group represented by CO—O—, an oxo group (O=), or a divalent group represented by R a1 ON = can be mentioned.
〔塩〕
　化合物（Ｉ）の塩は、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、硫酸などの無機酸の塩；酢酸、乳酸などの有機酸の塩；リチウム、ナトリウム、カリウムなどのアルカリ金属の塩；カルシウム、マグネシウムなどのアルカリ土類金属の塩；鉄、銅などの遷移金属の塩；トリエチルアミン、トリブチルアミン、ピリジン、ヒドラジンなどの有機塩基の塩；アンモニウム塩などを挙げることができる。 〔salt〕
Salts of compound (I) are not particularly limited as long as they are agriculturally and horticulturally acceptable salts. 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; salts of transition metals; salts of organic bases such as triethylamine, tributylamine, pyridine and hydrazine; and ammonium salts.
〔製造方法〕
　化合物（Ｉ）またはその塩の製造方法は、限定されない。例えば、本発明の化合物（Ｉ）またはその塩は、実施例などに記載したような公知の手法によって得ることができる。また、化合物（Ｉ）の塩は、化合物（Ｉ）から公知の手法によって得ることができる。 〔Production method〕
The method for producing compound (I) or a salt thereof is not limited. For example, compound (I) or a salt thereof of the present invention can be obtained by known methods such as those described in Examples. Also, a salt of compound (I) can be obtained from compound (I) by a known method.
〔農園芸用殺菌剤〕
　本発明の農園芸用殺菌剤は、化合物（Ｉ）およびその塩から選ばれる少なくともひとつを有効成分として含有するものである。本発明の農園芸用殺菌剤に含まれる化合物（Ｉ）またはその塩の量は、殺菌効果を示す限りにおいて特に制限されない。 [Fungicide for agriculture and horticulture]
The agricultural and horticultural fungicide of the present invention contains as an active ingredient at least one selected from compound (I) and salts thereof. The amount of compound (I) or a salt thereof contained in the agricultural and horticultural fungicide of the present invention is not particularly limited as long as it exhibits a fungicidal effect.
　本発明の農園芸用殺菌剤は、広範囲の種類の糸状菌、例えば、藻菌類（Oomycetes）、子のう（嚢）菌類（Ascomycetes）、不完全菌類（Deuteromycetes）、担子菌類（Basidiomycetes）、接合菌類（Zygomycetes）に属する菌に由来する植物病害の防除に使用できる。 The agricultural and horticultural fungicides of the present invention are suitable for a wide variety of filamentous fungi such as Oomycetes, Ascomycetes, Deuteromycetes, Basidiomycetes, zygotes. It can be used to control plant diseases caused by fungi belonging to Zygomycetes.
　防除の対象となる植物病害（病原菌）の例を以下に示す。
　テンサイ：褐斑病（Cercospora beticola）、黒根病（Aphanomyces cochlioides ）、根腐病（Thanatephorus cucumeris）、葉腐病（Thanatephorus cucumeris）、さび病（Uromyces betae）、うどんこ病（Oidium sp.）、斑点病（Ramularia beticola）、苗立枯病（Aphanomyces cochlioides、Pythium ultimum）など
　ラッカセイ：褐斑病（Mycosphaerella arachidis）、汚斑病（Ascochyta sp.）、さび病（Puccinia arachidis）、立枯病（Pythium debaryanum）、さび斑病（Alternaria alternata）、白絹病（Sclerotium rolfsii）黒渋病（Mycosphaerella berkeleyi）、黒根腐病（Calonectria ilicicola）など
　キュウリ：うどんこ病（Sphaerotheca fuliginea）、べと病（Pseudoperonospora cubensis）、つる枯病（Mycosphaerella melonis）、つる割病（Fusarium oxysporum）、菌核病（Sclerotinia sclerotiorum）、灰色かび病（Botrytis cinerea）、炭そ病（Colletotrichum orbiculare）、黒星病（Cladosporium cucumerinum）、褐斑病（Corynespora cassiicola）、苗立枯病（Pythium debaryanum、Rhizoctonia solani Kuhn）、ホモプシス根腐病（Phomopsis sp.）斑点細菌病（Pseudomonas syringae pv. Lachrymans）など
　トマト：灰色かび病（Botrytis cinerea）、葉かび病（Cladosporium fulvum）、疫病（Phytophthora infestans）、半身萎凋病（Verticillium albo-atrum、 Verticillium dahliae）、うどんこ病（Oidium neolycopersici）、輪紋病（Alternaria solani）、すすかび病（Pseudocercospora fuligena）、青枯病（Ralstonia solanacearum）、菌核病（Sclerotinia sclerotiorum）など
　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）、菌核病（Sclerotinia sclerotiorum）、半身萎凋病（Verticillium dahliae）、褐紋病（Phomopsis vexans）など
　トウガラシ：疫病（Phytophthora capsici）、灰色かび病（Botrytis cinerea）、菌核病（Sclerotinia sclerotiorum）、炭疽病（Colletotrichum aenigma、Colletotrichum capsici、 Colletotrichum fructicola、 Colletotrichum jiangxiense）、うどんこ病（Leveillula taurica）など
　イチゴ：灰色かび病（Botrytis cinerea）、うどんこ病（Sphaerotheca humuli）、炭そ病（Colletotrichum acutatum、Colletotrichum fragariae）、疫病（Phytophthora cactorum）、軟腐病（Rhizopus stolonifer）、萎黄病（Fusarium oxysporum）、萎凋病（Verticillium dahliae）、菌核病（Sclerotinia sclerotiorum）など
　タマネギ：灰色腐敗病（Botrytis allii）、灰色かび病（Botrytis cinerea）、白斑葉枯病（Botrytis squamosa）、べと病（Peronospora destructor）、白色疫病（Phytophthora porri）、小菌核病（Ciborinia allii）、小菌核腐敗病（Botrytis squamosa）、乾腐病（Fusarium oxysporum）、紅色根腐病（Pyrenochaeta terrestris）、黒腐菌核病（Sclerotium cepivorum）、さび病（Puccinia allii）、白絹病（Sclerotium rolfsii）など
　ネギ：軟腐病（Pectobacterium carotovorum）、べと病（Peronospora destructor）、葉枯病（Pleospora allii）、黒腐菌核病（Sclerotium cepivorum）、さび病（Puccinia allii）、白斑葉枯病（Botrytis squamosa）、白絹病（Sclerotium rolfsii）、紅色根腐病（Pyrenochaeta terrestris）など
　キャベツ：根こぶ病（Plasmodiophora brassicae）、軟腐病（Erwinia carotovora）、黒腐病（Xanthomonas campesrtis pv. campestris）、黒斑細菌病（Pseudomonas syringae pv. maculicola、P. s. pv. alisalensis）、べと病（Peronospora parasitica）、菌核病（Sclerotinia sclerotiorum）、黒すす病（Alternaria brassicicola）、灰色かび病（Botrytis cinerea）、根朽病（Phoma lingam）、ピシウム腐敗病（Pythium aphanidermatum, Pythium ultimum）、白さび病（Albugo macrospora）など
　レタス：腐敗病（Pseudomonas cichorii, Pseudomonas marginalis）、軟腐病（Pectobacterium carotovorum）、べと病（Bremia lactucae）、灰色かび病（Botrytis cinerea）、菌核病（Sclerotinia sclerotiorum）、ビッグベイン病（Mirafiori lettuce big-vein ophiovirus）、根腐病（Fusarium oxysporum）、すそ枯病（Rhizoctonia solani）、うどんこ病（Golovinomyces orontii）など
　インゲン：菌核病（Sclerotinia sclerotiorum）、灰色かび病（Botrytis cinerea）、炭疽病（Colletotrichum lindemuthianum）、角斑病（Phaeoisariopsis griseola）など
　エンドウ：褐紋病（Mycosphaerella blight）、灰色かび病（Botrytis cinerea）、菌核病（Sclerotinia sclerotiorum）、うどんこ病（Erysiphe pisi）など Examples of plant diseases (pathogens) targeted for control are shown below.
Sugar beet: brown spot (Cercospora beticola), cochlioides (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), spot Peanuts: Mycosphaerella arachidis, Ascochyta sp., Puccinia arachidis, Pythium debaryanum ), rust (Alternaria alternata), white silk (Sclerotium rolfsii), black stain (Mycosphaerella berkeleyi), black root rot (Calonectria ilicicola), etc. Cucumber: powdery mildew (Sphaerotheca fuliginea), downy mildew (Pseudoperonospora cubensis) , Mycosphaerella melonis, Fusarium oxysporum, Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum orbiculare, Cladosporium cucumerinum, Brown spot Corynespora cassiicola, Pythium debaryanum, Rhizoctonia solani Kuhn, Phomopsis sp., Pseudomonas syringae pv. Lachrymans, etc. Tomatoes: Botrytis cinerea, leaves Mold (Cladosporium fulvum), plague (Phytophthora infestans), wilt (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), ring spot (Alternaria solani), Pseudocercospora fuligena, Ralstonia solanacearum, Sclerotinia sclerotiorum, etc. Eggplant: Botrytis cinerea, Corynespora melongenae, Erysiphe cichoracearum), Mycovellosiella nattrassii, Sclerotinia sclerotiorum, Verticillium dahliae, Phomopsis vexans, etc. Pepper: Phytophthora capsici, Botrytis cinerea , Sclerotinia sclerotiorum, Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense, Leveillula taurica Strawberry: Botrytis cinerea, Sphaerotheca humuli , Colletotrichum acutatum, Colletotrichum fragariae, Phytophthora cactorum, Rhizopus stolonifer, Fusarium oxysporum, Verticillium dahliae, Sclerotinia sclerotiorum, etc. Onions: Gray Botrytis allii, Botrytis cinerea, Botrytis squamosa, Peronospora destructor, Phytophthora porri, Ciborinia allii, Small fungi nucleus rot (Botrytis squamosa), dry rot (Fusarium oxysporum), red root rot (Pyrenochaeta terrestris), black rot sclerotium (Sclerotium cepivorum), rust (Puccinia allii), white silk disease (Sclerotium rolfsii), etc. Green onions: soft rot (Pectobacterium carotovorum), downy mildew (Peronospora destructor), leaf blight (Pleospora allii), black rot (Sclerotium cepivorum), rust (Puccinia allii), leaf blight (Botrytis squamosa), white silk disease (Sclerotium rolfsii), red root rot (Pyrenochaeta terrestris), etc. Cabbage: clubroot (Plasmodiophora brassicae), soft rot (Erwinia carotovora), black rot (Xanthomonas campesrtis pv. campestris), black spot (Pseudomonas syringae pv. maculicola, P. s. pv. alisalensis), mildew (Peronospora parasitica), sclerotinia (Sclerotinia sclerotiorum) ), Black soot (Alternaria brassicicola), Gray mold (Botrytis cinerea), Root rot (Phoma lingam), Pythium aphanidermatum, Pythium ultimum, White rust (Albugo macrospora), etc. Lettuce: rot ( Pseudomonas cichorii, Pseudomonas marginalis, Pectobacterium carotovorum, Bremia lactucae, Botrytis cinerea, Sclerotinia sclerotiorum, Mirafiori lettuce big-vein ophiovirus, Fusarium oxysporum, Rhizoctonia solani, Golovinomyces orontii, etc. Green beans: Sclerotinia sclerotiorum, Botrytis cinere a), Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc. Peas: Mycosphaerella blight, Botrytis cinerea, Sclerotinia sclerotiorum, Erysiphe pisi )Such
　りんご：うどんこ病（Podosphaera leucotricha）、黒星病（Venturia inaequalis）、モニリア病（Monilinia mali）、黒点病（Mycosphaerella pomi）、腐らん病（Valsa mali）、斑点落葉病（Alternaria mali）、赤星病（Gymnosporangium yamadae）、輪紋病（Botryosphaeria berengeriana）、炭そ病（Glomerella cingulata、Colletotrichum acutatum）、褐斑病（Diplocarpon mali）、すす点病（Zygophiala jamaicensis）、すす斑病（Gloeodes pomigena）、紫紋羽病（Helicobasidium mompa）、白紋羽病（Rosellinia necatrix）、灰色かび病（Botrytis cinerea）、火傷病（Erwinia amylovora）、銀葉病（Chondrostereum purpureum）、根頭がんしゅ病（Rhizobium radiobacter 、 Rhizobium rhizogenes）など
　ウメ：黒星病（Cladosporium carpophilum）、灰色かび病（Botrytis cinerea）、灰星病（Monilinia mumecola）、すす斑病（Peltaster sp.）、ふくろ実病（Taphrina pruni）、褐色せん孔病（Phloeosporella padi）など
　カキ：うどんこ病（Phyllactinia kakicola）、炭そ病（Gloeosporium kaki）、角斑落葉病（Cercospora kaki）、円星落葉病（Mycosphaerella nawae）、灰色かび病（Botrytis cinerea）、すす点病（Zygophiala jamaicensis）など
　モモ：灰星病（Monilinia fructicola、Monilia fructigena）、黒星病（Cladosporiumcarpophilum）、ホモプシス腐敗病（Phomopsis sp.）、穿孔細菌病（Xanthomonas campestris pv. pruni）、縮葉病（Taphrina deformans）、炭そ病（Colletotrichum gloeosporioides）、褐色せん孔病（Phloeosporella padi）、かわらたけ病（Coriolus versicolor）など
　アーモンド：灰星病（Monilinia laxa）、斑点病（Stigmina carpophila）、黒星病（Cladosporium carpophilum）、葉ぶくれ病（Polystigma rubrum）、斑点落葉病（Alternaria alternata）、炭疽病（Colletotrichum gloeospoides）など
　オウトウ：灰星病（Monilinia fructicola）、炭そ病（Colletotrichum acutatum）、黒斑病（Alternaria sp.）、幼果菌核病（Monilinia kusanoi）、褐色せん孔病（Mycosphaerella cerasella）、うどんこ病（Podosphaera tridactyla）など
　ブドウ：灰色かび病（Botrytis cinerea）、うどんこ病（Uncinula necator）、晩腐病（Glomerella cingulata、Colletotrichum acutatum）、べと病（Plasmopara viticola）、黒とう病（Elsinoe ampelina）、褐斑病（Pseudocercospora vitis）、黒腐病（Guignardia bidwellii）、白腐病（Coniella castaneicola）、さび病（Phakopsora ampelopsidis）、白色綿雪症（病原菌未同定）、根頭がんしゅ病（Rhizobium radiobacter、 Rhizobium vitis）など
　ナシ：黒星病（Venturia nashicola）、赤星病（Gymnosporangium asiaticum）、黒斑病（Alternaria kikuchiana）、輪紋病（Botryosphaeria berengeriana）、うどんこ病（Phyllactinia mali）、胴枯病（Phomopsis fukushii）、褐色斑点病（Stemphylium vesicarium）、炭そ病（Glomerella cingulata）など
　チャ：輪斑病（Pestalotiopsis longiseta、 P. theae）、炭そ病（Colletotrichum theae-sinensis）、網もち病（Exobasidium reticulatum）、赤焼病（Pseudomonas syringae）、もち病（Exobasidium vexans）など
　カンキツ：そうか病（Elsinoe fawcettii）、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）、うどんこ病（Oidium sp.）、疫病（Phytophthora citrophthora）、炭そ病（Colletotrichum fioriniae）など
　キウイフルーツ：花腐細菌病（Pseudomonas marginalis、Pseudomonas syringae、Pseudomonas viridiflava）、かいよう病（Pseudomonas syringae）、灰色かび病（Botrytis cinerea）、果実軟腐病（Botryosphaeria dothidea、Diaporthe sp.、Lasiodiplodia theobromae）、すす斑病（Pseudocercospora actinidiae）など
　オリーブ：炭疽病（Colletotrichum acutatum, Colletotrichum gloeosporioides）、eacock spot（Spilocaea oleaginea）など
　クリ：炭疽病（Colletotrichum gloeosporioides）など Apples: powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), monilia (Monilinia mali), black spot (Mycosphaerella pomi), rot (Valsa mali), leaf spot (Alternaria mali), scab (Gymnosporangium) yamadae), ring spot (Botryosphaeria berengeriana), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), soot spot (Zygophiala jamaicensis), soot spot (Gloeodes pomigena), purple leaf spot (Helicobasidium mompa), White leaf disease (Rosellinia necatrix), Gray mold (Botrytis cinerea), Fire blight (Erwinia amylovora), Silver leaf disease (Chondrostereum purpureum), Root canker (Rhizobium radiobacter, Rhizobium rhizogenes) Plum: Cladosporium carpophilum, Botrytis cinerea, Monilinia mumecola, Peltaster sp., Taphrina pruni, Phloeosporella padi Oysters: powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), horn spot (Cercospora kaki), leaf spot (Mycosphaerella nawae), gray mold (Botrytis cinerea), soot spot (Zygophiala) jamaicensis), etc. Peach: Monilinia fructicola, Monilia fructigena, Cladosporiumcarpophilum, Phomopsis sp., Xanthomonas campestris pv. pruni, Taphrina deformans, charcoal Colletotrichum gloeosporioides, Phloeosporella padi, Coriolus versicolor, etc. Almonds: Monilinia laxa, Stigmina carpophila, Cladosporium carpophilum, leaf blisters Polystigma rubrum, Alternaria alternata, Colletotrichum gloeospoides, etc. Cherry: Monilinia fructicola, Colletotrichum acutatum, Alternaria sp., young fruit Sclerotinia (Monilinia kusanoi), brown pit (Mycosphaerella cerasella), powdery mildew (Podosphaera tridactyla), etc. Grapes: Botrytis cinerea, powdery mildew (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum) acutatum), downy mildew (Plasmopara viticola), black rot (Elsinoe ampelina), brown spot (Pseudocercospora vitis), black rot (Guignardia bidwellii), white rot (Coniella castaneicola), rust (Phakopsora ampelopsidis), Snow white (pathogen unidentified), root cancer (Rhizobium radiobacter, Rhizobium vitis), etc. Pear: Venturia nashicola, Gymnosporangium asiaticum, Alternaria kikuchiana, Ring spot (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown spot (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: Pestalotiops is longiseta, P. theae), anthracnose (Colletotrichum theae-sinensis), net blister (Exobasidium reticulatum), red scorch (Pseudomonas syringae), blast (Exobasidium vexans), etc. Citrus: scab (Elsinoe fawcettii) , Penicillium italicum, Penicillium digitatum, Botrytis cinerea, Diaporthe citri, Xanthomonas campestris pv. Citri, Powdery mildew (Oidium sp.), Late blight (Phytophthora citrophthora), anthracnose (Colletotrichum fioriniae), etc. Kiwifruit: Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava, Pseudomonas syringae, Botrytis cinerea, fruit soft rot (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), Pseudocercospora actinidiae, etc. Olive: Colletotrichum acutatum, Colletotrichum gloeosporioides, eacock spot (Spilocaea oleaginea), etc. Chestnut: Colletotrichum gloeosporioides, etc.
　コムギ：うどんこ病（Blumeria graminis f.sp. tritici）、赤かび病（Gibberella zeae、Fusarium avenaceum、Fusarium culmorum、Fusarium crookwellense、Microdochium nivale）、赤さび病（Puccinia recondita）、黄さび病（Puccinia striiformis）、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（Gaeumannomyces graminis）、麦角病（Claviceps purpurea）、なまぐさ黒穂病（Tilletia caries）、裸黒穂病（Ustilago nuda）、いもち病（Pyricularia grisea）、Damping off（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）、Seedling blight（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）など
　オオムギ：斑葉病（Pyrenophora graminea）、網斑病（Pyrenophora teres）、雲形病（Rhynchosporium secalis）、裸黒穂病（Ustilago tritici、U.nuda）、Damping off（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）、Seedling blight（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）など
　イネ：いもち病（Pyricularia oryzae）、紋枯病（Rhizoctonia solani）、馬鹿苗病（Gibberella fujikuroi）、ごま葉枯病（Cochliobolus miyabeanus）、苗立枯病（Pythiumgraminicola）、白葉枯病（Xanthomonas oryzae）、苗立枯細菌病（Burkholderia plantarii）、褐条病（Acidovorax avenae）、もみ枯細菌病（Burkholderia glumae）、すじ葉枯病（Cercospora oryzae）、稲こうじ病（Ustilaginoidea virens）、褐色米（Alternaria alternata、Curvularia intermedia）、腹黒米（Alternaria padwickii）、紅変米（Epicoccum purpurascens）など
　タバコ：菌核病（Sclerotinia sclerotiorum）、うどんこ病（Erysiphe cichoracearum）、疫病（Phytophthora nicotianae）、など
　チューリップ：灰色かび病（Botrytis cinerea）、褐色斑点病（Botrytis tulipae）、葉腐病（Rhizoctonia solani）、球根腐敗病（Fusarium oxysporum）、皮腐病（Rhizoctonia solani）など
　バラ：黒星病（Diplocarpon rosae）、うどんこ病（Erysiphe simulans、Podosphaera pannosa）、灰色かび病（Botrytis cinerea）など
　キク：灰色かび病（Botrytis cinerea）、白さび病（Puccinia horiana）、べと病（Paraperonospora minor, Peronospora danica）、ピシウム立枯病（Pythium aphanidermatum、Pythium dissotocum、Pythium helicoides、Pythium oedochilum、Pythium sylvaticum）、立枯病（Rhizoctonia solani）、フザリウム立枯病（Fusarium solani）など
　ガーベラ：灰色かび病（Botrytis cinerea）、うどんこ病（Podosphaera xanthii）など
　ユリ：葉枯病（Botrytis elliptica, Pestalotiopsis sp.）、灰色かび病（Botrytis cinerea）など
　ヒマワリ：べと病（Plasmopara halstedii）、菌核病（Sclerotinia sclerotiorum）、灰色かび病（Botrytis cinerea）など
　ベントグラス：雪腐大粒菌核病（Sclerotinia borealis）、ラージパッチ（Rhizoctonia solani）、ブラウンパッチ（Rhizoctonia solani）、ダラースポット（Sclerotinia homoeocarpa）、いもち病（Pyricularia sp.）、赤焼病（Pythium aphanidermatum）、炭そ病(Colletotrichum graminicola)など
　オーチャードグラス：うどんこ病（Erysiphe graminis）など
　ダイズ：紫斑病（Cercospora kikuchii）、べと病（Peronospora manshurica）、茎疫病（Phytophthora sojae）、さび病（Phakopsora pachyrhizi）、菌核病（Sclerotinia sclerotiorum）、炭そ病（Colletotrichum truncatum）、灰色かび病（Botrytis cinerea）、黒とう病（Elsinoe glycines)、黒点病（Diaporthe phaseolorum var. sojae）、Damping off（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）、Seedling blight（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）など
　ジャガイモ：疫病（Phytophthora infestans）、夏疫病（Alternaria solani）、黒あざ病（Thanatephorus cucumeris）、半身萎凋病（Verticillium albo－atrum、V. dahliae、V. nigrescens）、黒あし病（Pectobacterium atrosepticum）、軟腐病（Pectobacterium carotovorum）、灰色かび病（Botrytis cinerea）、そうか病（Streptomyces spp.）、菌核病（Sclerotinia sclerotiorum）など
　ヤマノイモ：葉渋病（Cylindrosporium dioscoreae）、炭疽病（Colletotrichum gloeosporioides）、青かび病（Penicillium sclerotigenum）など
　サツマイモ：紫紋羽病（Helicobasidium mompa）、つる割病（Fusarium oxysporum）など
　サトイモ：疫病（Phytophthora colocasiae）、茎腐病（Rhizoctonia solani）など
　ショウガ：根茎腐敗病（Pythium ultimum、Pythium myriotylum）、白星病（Phyllosticta zingiberis）など
　バナナ：パナマ病（Fusarium oxysporum）、シガトカ病（Mycosphaerella fijiensis、M. musicola）など
　マンゴー：炭そ病（Colletotrichum aenigma）、かいよう病（Xanthomonas campestris）、軸腐病（Diaporthe pseudophoenicicola、Lasiodiplodia theobromae、Lasiodiplodia spp.、Neofusicoccum parvum、Neofusicoccum sp.）、灰色かび病（Botrytis cinerea）など
　ナタネ：菌核病（Sclerotinia sclerotiorum）、根朽病（Phoma lingam）、黒斑病（Alternaria brassicae）、うどんこ病（Erysiphe cruciferarum、Erysiphe cichoracearum、Oidium matthiolae）、べと病（Peronospora parasitica）など
　コーヒー：さび病（Hemileia vastatrix）、炭疽病（Colletotrichum coffeanum）、褐眼病（Cercospora coffeicola）など
　サトウキビ：褐さび病（Puccinia melanocephala）など
　トウモロコシ：ひょう紋病（Gloeocercospora sorghi）、さび病（Puccinia sorghi）、南方さび病（Puccinia polysora）、黒穂病（Ustilago maydis）、ごま葉枯病（Cochliobolus heterostrophus）、すす紋病（Setosphaeria turcica）、Damping off（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）、Seedling blight（Pythium spp.、Fusariumspp.、Rhizoctonia spp.）など
　ワタ：苗立枯病（Pythium sp.）、さび病（Phakopsora　gossypii）、白かび病（Mycosphaerella areola）、炭疽病（Glomerella gossypii）など
　ホップ：べと病（Pseudoperonospora humuli）、うどんこ病（Oidium sp.、Podosphaera macularis）、灰色かび病（Botrytis cinerea）など Wheat: Powdery mildew (Blumeria graminis f.sp. tritici), Fusarium head blight (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), Fusarium rust (Puccinia recondita), Yellow rust (Puccinia striiformis), Pythium iwayamai, Monographella nivalis, Pseudocercosporella herpotrichoides, Septoria tritici, Leptosphaeria nodorum, Typhula incarnata), Myriosclerotinia borealis, Gaeumannomyces graminis, Claviceps purpurea, Tilletia caries, Ustilago nuda, Pyricularia grisea ), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Barley: Pyrenophora graminea, Pyrenophora teres ), Rhynchosporium secalis, Naked smut (Ustilago tritici, U.nuda), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp. Rice: Pyricularia oryzae, Rhizoctonia solani, Gibberella fujikuroi, Cochliobolus miyabeanus, Pythiumg raminicola), Xanthomonas oryzae, Burkholderia plantarii, Acidovorax avenae, Burkholderia glumae, Cercospora oryzae, Rice blight (Ustilaginoidea virens), Brown rice (Alternaria alternata, Curvularia intermedia), Alternaria padwickii, Epicoccum purpurascens, etc. Tobacco: Sclerotinia sclerotiorum, Erysiphe cichoracearum, plague ( Phytophthora nicotianae), etc. Tulips: Botrytis cinerea, Botrytis tulipae, Rhizoctonia solani, Fusarium oxysporum, Rhizoctonia solani, etc. Rose: Black star Diplocarpon rosae, powdery mildew (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc. Peronospora danica), Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum, Rhizoctonia solani, Fusarium solani, etc. Gerbera: Botrytis cinerea ), powdery mildew (Podosphaera xanthii), etc. Lily: leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc. Sunflower: downy mildew (Pla smopara halstedii), Sclerotinia sclerotiorum, Botrytis cinerea, etc. Bent grass: Sclerotinia borealis, large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), dollar spot ( Sclerotinia homoeocarpa), Pyricularia sp., Pythium aphanidermatum, Colletotrichum graminicola, etc. Orchard grass: Powdery mildew (Erysiphe graminis), etc. Soybean: Purpura (Cercospora kikuchii), downy mildew Peronospora manshurica, Phytophthora sojae, Phakopsora pachyrhizi, Sclerotinia sclerotiorum, Colletotrichum truncatum, Botrytis cinerea, Elsinoe glycines ), Black spot (Diaporthe phaseolorum var. sojae), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. Potatoes: Phytophthora infestans ), Alternaria solani, Thanatephorus cucumeris, Verticillium albo-atrum, V. dahliae, V. nigrescens, Pectobacterium atrosepticum, Pectobacterium carotovorum, Gray mold (Botrytis cinerea), scab (Streptomyces spp.), sclerotinia (Sclerotinia sclerotiorum), etc. sporium dioscoreae, Colletotrichum gloeosporioides, Penicillium sclerotigenum, etc. Sweet potato: Helicobasidium mompa, Fusarium oxysporum, etc. Taro: Phytophthora colocasiae, Rhizoctonia solani), etc. Ginger: Root rot (Pythium ultimum, Pythium myriotylum), White star disease (Phyllosticta zingiberis), etc. Banana: Panama disease (Fusarium oxysporum), Sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc. Mango: Anthracnose (Colletotrichum) aenigma), canker (Xanthomonas campestris), shaft rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), gray mold (Botrytis cinerea), etc. Rapeseed: Sclerotinia sclerotiorum, root rot (Phoma lingam), black spot (Alternaria brassicae), powdery mildew (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), downy mildew (Peronospora parasitica), etc. Coffee: rust (Hemileia vastatrix), anthracnose ( Coletotrichum coffeanum), brown eye disease (Cercospora coffeicola), etc. Sugarcane: Brown rust (Puccinia melanocephala), etc. Corn: Gloeocercospora sorghi, rust (Puccinia sorghi), southern rust (Puccinia polysora), smut (Ustilago) maydis), sesame leaf blight (Cochliobolus hetero strophus), Setosphaeria turcica, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc. sp.), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc. Hops: Downy mildew (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold disease (Botrytis cinerea), etc.
〔殺線虫剤〕
　本発明の含窒素ヘテロアリール化合物は、植物の生育に影響する各種の線虫類の防除効果にも優れている。
　本発明の殺線虫剤は、化合物（Ｉ）およびその塩から選ばれる少なくともひとつを有効成分として含有するものである。本発明の殺線虫剤に含まれる化合物（Ｉ）またはその塩の量は、線虫の防除効果を示す限りにおいて特に制限されない。 [Nematicide]
The nitrogen-containing heteroaryl compound of the present invention also has an excellent control effect against various nematodes that affect plant growth.
The nematicide of the present invention contains at least one selected from compound (I) and salts thereof as an active ingredient. The amount of compound (I) or a salt thereof contained in the nematicide of the present invention is not particularly limited as long as it exhibits a nematode control effect.
　本発明の殺線虫剤によって防除可能な各種の植物寄生性線虫類の具体例を以下に示す。（１）クキセンチュウ目（Tylenchida）
（a）アングイナ科（Anguinidae）の、例えば、アングイナ属種（Anguina spp.）の、アングイナ・フネスタ（Anguina funesta）、コムギツブセンチュウ　（Anguina tritici）；ジチレンクス属種（Ditylenchus spp.）の、イモグサレセンチュウ　（Ditylenchus destructor）、ナミクキセンチュウ（Ditylenchus dipsaci）、キノコセンチュウ　（Ditylenchus myceliophagus）；
（b）アフェレンコイデス科（Aphelenchoididae）の、例えば、アフェレンコイデス属種（Aphelenchoides spp.）の、イネシンガレセンチュウ　（Aphelenchoides besseyi）、イチゴセンチュウ　（Aphelenchoides fragariae）、ハガレセンチュウ　（Aphelenchoides ritzemabosi）；ブルサフェレンクス属種（Bursaphelenchus spp.）の、マツノザイセンチュウ（Bursaphelenchus xylophilus）；
（c）ベロノライムス科（Belonolaimidae）の、例えば、ベロノライムス属種（Belonolaimus spp.）の、ベロノライムス・ロンギカウダツス（Belonolaimus longicaudatus）；チレンコリンクス属種（Tylenchorhynchus spp.）の、ナミイシュクセンチュウ　（Tylenchorhynchus claytoni）、チレンコリンクス・ズビウス（Tylenchorhynchus dubius）；
（d）クリコネマ科（Criconematidae）の、例えば、クリコネマ・ムタビル（Criconema mutabile);
（e）ドリコドルス科（Dolichodoridae）の、例えば、ドリコドルス・メディテラネウス（Dolichodorus mediterraneus）；
（f）エクフャドフォラ科（Ecphyadophoridae）の、例えば、エクフャドフォラ・テヌイシマ（Ecphyadophora tenuissima）
（g）ヘミシクリオフォラ科（Hemicycliophoridae）の、例えば、ローフィア・チエネマニ（Loofia thienemanni）；
（h）ヘテロデラ科（Heteroderidae）の、例えば、グロボデラ属種（Globodera spp.）の、ジャガイモシストセンチュウ　（Globodera rostochiensis）、ジャガイモシロシストセンチュウ　（Globodera pallida）、タバコシストセンチュウ　（Globodera tabacum）；ヘテロデア属種（Heterodera spp.）の、ムギシストセンチュウ　（Heterodera avenae）、ヘテロデア・フルシフェラ（Heterodera cruciferae）、ダイズシストセンチュウ　（Heterodera glycines）、テンサイシストセンチュウ　（Heterodera schachtii）、ク
ローバシストセンチュウ　（Heterodera trifolii）；
（i）ホプロライムス科（Hoplolaimidae）の、例えば、ヘリコチレンクス属種（Helicotylenchus spp.）の、ナミラセンセンチュウ　（Helicotylenchus dihystera）、ヘリコチレンクス・ムルチシンクツス（Helicotylenchus multicinctus）；ホプロライムス属種（Hoplolaimus spp.）の、ホプロライムス・コロンブス（Hoplolaimus columbus）、ホプロライムス・ガレアツス（Hoplolaimus galeatus）；その他の、ロチレンカス・ロブスタス（Rotylenchus robustus）、ロチレンクルス・レニホルミス（Rotylenchulus reniformis）；
（j）メロイドギネ科（Meloidogynidae）の、例えば、メロイドギネ属種の（Meloidogynespp.）、アレナリアネコブセンチュウ　（Meloidogyne arenaria）、コロンビアネコブセンチュウ　（Meloidogyne chitwoodi）、キタネコブセンチュウ　（Meloidogyne hapla）、サツマイモネコブセンチュウ　（Meloidogyne incognita）、ジャワネコブセンチュウ（Meloidogyne javanica）、テムズネコブセンチュウ（Meloidogyne thamesi）；
（k）ノスティレンクス科（Nothotylenchidae）の、例えば、イチゴメセンチュウ（Nothotylenchus acris）；
（l）パラティレンクス科（Paratylenchidae）の、例えば、パラティレンクス属種（Paratylenchus spp.）の、チャピンセンチュウ（Paratylenchus curvitatus）、ヒメピンセンチュウ（Paratylenchus elachistus）；
（m）プラティレンクス科（Pratylenchidae）の、例えば、プラティレンクス属（Pratylenchus spp.）種の、プラティレンクスネグサレセンチュウ（Pratylenchus brachyurus）、ミナミネグサレセンチュウ（Pratylenchus coffeae）、ピンセンチュウ（Pratylenchus curvitatus）、キクネグサレセンチュウ（Pratylenchus fallax）、プラティレンクス・ゴーデイ（Pratylenchus goodeyi）、プラティレンクス・ネグレクツス（Pratylencus neglectus）、キタネグサレセンチュウ（Pratylenchus penetrans）、プラティレンクス・スクリブネリ（Pratylenchus scribneri）、クルミネグサレセンチュウ（Pratylenchus vulnus）、モロコシネグサレセンチュウ　（Pratylenchus zeae）；その他の、ニセネコブセンチュウ（Nacobbus aberrans）、バナナネモグリセンチュウ　（Radopholus similis）、ミカンネセンチュウ　（Tylenchulus semipenetrans）、カンキツネモグリセンチュウ（Radopholus citrophilus）。 Specific examples of various plant parasitic nematodes that can be controlled by the nematicide of the present invention are shown below. (1) Tylenchida
(a) Anguinidae, for example, Anguina spp., Anguina funesta, Anguina tritici; Ditylenchus spp., Imogusare nematode ( Ditylenchus destructor), Namiki Nematode (Ditylenchus dipsaci), Mushroom Nematode (Ditylenchus myceliophagus);
(b) Aphelenchoides family (Aphelenchoididae), for example, Aphelenchoides spp., Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi; Bursaphelenchus xylophilus, of the genus Bursaphelenchus spp.;
(c) Belonolaimidae, e.g., Belonolaimus spp., Belonolaimus longicaudatus; Tylenchorhynchus spp., Tylenchorhynchus claytoni , Tylenchorhynchus dubius;
(d) of the family Criconematidae, such as Criconema mutabile;
(e) of the family Dolichoodoridae, such as Dolichoodorus mediterraneus;
(f) Ecphyadophoridae, for example, Ecphyadophora tenuissima
(g) Hemicycliophoridae, such as Loofia thienemanni;
(h) Globodera rostochiensis, Globodera pallida, Globodera tabacum of the family Heteroderidae, e.g. Globodera spp.; (Heterodera spp.), Heterodera avenae, Heterodera cruciferae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii;
(i) of the family Hoplolimidae, for example, Helicotylenchus spp., Helicotylenchus dihystera, Helicotylenchus multicinctus; Columbus (Hoplolaimus columbus), Hoplolaimus galeatus; Others, Rotylenchus robustus, Rotylenchus reniformis;
(j) Meloidogyne family (Meloidogynidae), for example, Meloidogyne spp. Meloidogyne javanica, Meloidogyne thamesi;
(k) of the family Nothotylenchidae, such as Nothotylenchus acris;
(l) Paratylenchidae, for example, Paratylenchus spp., Paratylenchus curvitatus, Paratylenchus elachistus;
(m) Pratylenchus family (Pratylenchidae), for example, Platylenchus spp. species, Platylenchus brachyurus, Pratylenchus coffeae, Pinnematode (Pratylenchus curvitatus) ), Pratylenchus fallax, Pratylenchus goodeyi, Pratylencus neglectus, Pratylenchus penetrans, Platylenchus scribneri, Rumi-negative nematode (Pratylenchus vulnus), sorghum nematode (Pratylenchus zeae); others, root-knot nematode (Nacobbus aberrans), banana leaf nematode (Radopholus similis), orange nematode (Tylenchulus semipenetrans), citrus nematode (Radopholus) citrophilus).
（２）ドリライムス目（Dorylaimida）
（a）ロンギドルス科（Longidoridae）の、例えば、ロンギドルス属種（Longidorus spp.）の、ロンギドルス・エロンガテス（Longidorus elongates）；キシフィネマ属種（Xiphinema）の、アメリカオオハリセンチュウ　（Xiphinema americanum）、キシフィネマ・ブレビコーレ（Xiphinema brevicolle）、ブドウオオハリセンチュウ　（Xiphinema index）、キシフィネマ・ディバーシカウダツム（Xiphinema diversicaudatum）。 (2) Dorylaimida
(a) Longidoridae, e.g., Longidorus spp., Longidorus elongates; Xiphinema, Xiphinema americanum, Xiphinema brevicole (Xiphinema brevicolle), Grape Nematode (Xiphinema index), Xiphinema diversicaudatum (Xiphinema diversicaudatum).
（３）トリプロンキダ目（Triplonchida）
（a）トリコドルス科（Trichodoridae）の、例えば、トリコドルス・プリミチブス（Trichodorus primitivus）、ヒメユミハリセンチュウ（Paratrichodorus minor）。 (3) Triplonchida
(a) Trichodoridae family (Trichodoridae), for example, Trichodorus primitibus (Trichodorus primitibus), Nematode nematode (Paratrichodorus minor).
〔施用方法・混合剤〕
　本発明の農園芸用殺菌剤または殺線虫剤は、穀物類；野菜類；根菜類；イモ類；果樹類、茶、コーヒー、カカオなどの樹木類；牧草類；芝類；ワタなどの植物に対して用いることが好ましい。 [Method of application/mixture]
The agricultural and horticultural fungicides or nematicides of the present invention are grains; vegetables; root vegetables; potatoes; fruit trees, tea, coffee, trees such as cacao; It is preferably used for
　本発明の農園芸用殺菌剤は、植物類の各部位、たとえば、葉、茎、柄、花、蕾、果実、種子、スプラウト、根、塊茎、塊根、苗条、挿し木などに施用することができる。殺線虫剤は、根、塊茎、塊根などに施用することができる。また、これら植物類の改良品種・変種、栽培品種、さらには突然変異体、ハイブリッド体、遺伝子組み換え体（ＧＭＯ）を対象とすることもできる。 The agricultural and horticultural fungicide of the present invention can be applied to various parts of plants, such as leaves, stems, stems, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots and cuttings. . Nematicides can be applied to roots, tubers, root tubers, and the like. In addition, improved cultivars/varieties, cultivated cultivars, mutants, hybrids, and genetically modified organisms (GMO) of these plants can also be targeted.
　本発明の農園芸用殺菌剤は、花卉、芝、牧草を含む農園芸作物に発生する種々の病害の防除をするために行われる種子処理、茎葉散布、土壌施用、水面施用などに使用することができる。殺線虫剤は、種子処理、土壌施用などに使用することができる。 The agricultural and horticultural fungicide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. for the control of various diseases occurring in agricultural and horticultural crops including flowers, lawns, and pastures. can be done. Nematicides can be used in seed treatments, soil applications, and the like.
　本発明の農園芸用殺菌剤または殺線虫剤は、本発明の含窒素ヘテロアリール化合物以外の成分を含有してもよい。他の成分として、製剤化のために使用する公知の担体などを挙げることができる。また、他の成分として、従来公知の、殺菌剤、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、植物調節剤、共力剤、肥料、土壌改良剤、動物用飼料などを挙げることができる。このような他の成分を含有することによって、相乗効果を奏することがある。
　すなわち、本発明の態様のひとつとしては、１つ以上のさらなる殺菌剤を含む農園芸用殺菌剤を挙げることができる。 The agricultural and horticultural fungicide or nematicide of the present invention may contain components other than the nitrogen-containing heteroaryl compound of the present invention. Other components include known carriers used for formulation. Examples of other components include conventionally known fungicides, insecticides/miticides, nematicides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds, and the like. be able to. A synergistic effect may be produced by containing such other components.
Thus, one aspect of the present invention is an agricultural and horticultural fungicide containing one or more additional fungicides.
　本発明の農園芸用殺菌剤または殺線虫剤と混用または併用することができる、殺菌剤の具体例を以下に示す。
（１）核酸生合成阻害剤：
　（ａ）ＲＮＡポリメラーゼＩ阻害剤：ベナラキシル、ベナラキシル－Ｍ、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；クロジラコン、オフレース；
　（ｂ）アデノシンデアミナーゼ阻害剤：ブピリメート、ジメチリモール、エチリモール；
　（ｃ）ＤＮＡ／ＲＮＡ合成阻害剤：ヒメキサゾール、オクチリノン；
　（ｄ）ＤＮＡトポイソメラーゼII阻害剤：オキソリン酸。 Specific examples of fungicides that can be mixed or used together with the agricultural and horticultural fungicide or nematicide of the present invention are shown below.
(1) nucleic acid biosynthesis inhibitors:
(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl;
(b) adenosine deaminase inhibitors: bupirimate, dimethylmol, ethylimol;
(c) DNA/RNA synthesis inhibitors: Hymexazole, Octilinone;
(d) DNA topoisomerase II inhibitor: oxolinic acid.
（２）有糸核分裂阻害剤および細胞分裂阻害剤：
　（ａ）β－チューブリン重合阻害剤：ベノミル、カルベンダジム、クロルフェナゾール、フベリダゾール、チアベンダゾール；チオファネート、チオファネートメチル；ジエトフェンカルブ；ゾキサミド；エタボキサム；
　（ｂ）細胞分裂阻害剤：ペンシクロン；
　（ｃ）スペクトリン様タンパク質の非局在化阻害剤：フルオピコリド、フルオピモミド。 (2) mitotic inhibitors and cytostatic agents:
(a) beta-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; diethofencarb; zoxamide; ethaboxam;
(b) a cytostatic agent: pencicron;
(c) delocalized inhibitors of spectrin-like proteins: fluopicolide, fluopimimide.
（３）呼吸阻害剤：
　（ａ）複合体Ｉ－ＮＡＤＨ酸化還元酵素阻害剤：ジフルメトリム；トルフェンピラド；
　（ｂ）複合体II－コハク酸脱水素酵素阻害剤：ベノダニル、フルトラニル、メプロニル；イソフェタミド；フルオピラム；フェンフラム、フルメシクロックス；カルボキシン、オキシカルボキシン；チフルザミド；ベンゾビンジフルピル、ビキサフェン、フルキサピロキサド、フラメトピル、イソピラザム、ペンフルフェン、ペンチオピラド、セダキサン；ボスカリド、ピジフルメトフェン、イソフルシプラム、ピラジフルミド、インピルフルキサム(inpyrfluxam)；
　（ｃ）複合体III－ユビキノールオキシダーゼＱｏ阻害剤：アゾキシストロビン、クモキシストロビン、クメトキシストロビン、エノキサストロビン、フルフェノキシストロビン、ピコキシストロビン、ピラオキシストロビン；ピラクロストロビン、ピラメトストロビン、トリクロピリカルブ；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、フェナミンストロビン、メトミノストロビン、オリサストロビン；ファモキサドン；フルオキサストロビン；フェンアミドン；ピリベンカルブ；メチルテトラプロール；マンデストロビン；
　（ｄ）複合体III－ユビキノール還元酵素Ｑｉ阻害剤：シアゾファミド；アミスルブロ
ム；フェンピコキサミド；
　（ｅ）酸化的リン酸化の脱共役剤：ビナパクリル、メプチルジノカップ、ジノカップ；フルアジナム；フェリムゾン；
　（ｆ）酸化的リン酸化阻害剤（ＡＴＰ合成酵素の阻害剤）：フェンチンアセテート、塩化フェンチン、水酸化フェンチン；
　（ｇ）ＡＴＰ生産阻害剤：シルチオファム；
　（ｈ）複合体III：チトクロームｂｃ１（ユビキノン還元酵素）のＱｘ（未知）阻害剤
：アメトクトラジン。 (3) respiratory inhibitors:
(a) complex I-NADH oxidoreductase inhibitors: diflumetrim; tolfenpyrad;
(b) complex II-succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil; isofetamide; fluopyram; fenfuram, flumeciclox; carboxin, oxycarboxin; sado, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid, pydiflumetofen, isoflurcipram, pyraziflumide, inpyrfluxam;
(c) complex III-ubiquinol oxidase Qo inhibitors: azoxystrobin, comoxistrobin, cumethoxstrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraoxystrobin; pyraclostrobin , pyrametostrobin, triclopiricarb; cresoxime-methyl, trifloxystrobin; dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin; famoxadone; fluoxastrobin; Destrobin;
(d) complex III-ubiquinol reductase Qi inhibitors: cyazofamid; amisulbrom; fenpicoxamide;
(e) uncouplers of oxidative phosphorylation: binapacryl, meptyldinocap, dinocap; fluazinam; ferimzone;
(f) oxidative phosphorylation inhibitors (inhibitors of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(g) ATP production inhibitor: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): amethoctrazine.
（４）アミノ酸およびタンパク質合成阻害剤：
　（ａ）メチオニン生合成阻害剤：アンドプリム、シプロジニル、メパニピリム、ピリメタニル；
　（ｂ）タンパク質合成阻害剤：ブラストサイジン－Ｓ、カスガマイシン、カスガマイシン塩酸塩、ストレプトマイシン、オキシテトラサイクリン。 (4) amino acid and protein synthesis inhibitors:
(a) methionine biosynthesis inhibitors: andoprim, cyprodinil, mepanipyrim, pyrimethanil;
(b) protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.
（５）シグナル伝達阻害剤：
　（ａ）シグナル伝達阻害剤：キノキシフェン、プロキナジド；
　（ｂ）浸透圧シグナル伝達におけるＭＡＰ・ヒスチジンキナーゼ阻害剤：フェンピクロニル、フルジオキソニル；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。 (5) signaling inhibitor:
(a) signaling inhibitors: quinoxifene, proquinazide;
(b) MAP and histidine kinase inhibitors in osmotic signaling: fenpicronil, fludioxonil; clozolinate, iprodione, procymidone, vinclozolin.
（６）脂質および細胞膜合成阻害剤：
　（ａ）リン脂質生合成、メチルトランスフェラーゼ阻害剤：エジフェンホス、イプロベンホス、ピラゾホス；イソプロチオラン；
　（ｂ）脂質の過酸化剤：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、トルクロホスメチル；エトリジアゾール；
　（ｃ）細胞膜に作用する剤：ヨードカルブ、プロパモカルブ、プロパモカルブ塩酸塩、プロパモカルブホセチレート、プロチオカルブ。 (6) Lipid and Cell Membrane Synthesis Inhibitors:
(a) phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenfos, pyrazophos; isoprothiolane;
(b) lipid peroxidants: biphenyl, chloroneb, dichlorane, quintozene, technazene, tolclofos-methyl; etridiazole;
(c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb.
（７）細胞膜のステロール生合成阻害剤：
　（ａ）ステロール生合成におけるＣ１４位の脱メチル化阻害剤：トリホリン；ピリフェノックス、ピリソキサゾール；フェナリモル、フルルプリミドール、ヌアリモル；イマザリル、イマザリル硫酸塩、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、ビニコナゾール；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、ジクロブトラゾール、ジフェノコナゾール、ジニコナゾール、ジニコナゾール－Ｍ、エポキシコナゾール、エタコナゾール、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、フルトリアホール、フルコナゾール、フルコナゾール－シス、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、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；プロチオコナゾール、ボリコナゾール、メフェントリフルコナゾール；
　（ｂ）ステロール生合成におけるΔ１４還元酵素およびΔ８→Δ７－イソメラーゼの阻害剤：アルジモルフ、ドデモルフ、ドデモルフ酢酸塩、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；
　（ｃ）ステロール生合成系のＣ４位脱メチル化における３－ケト還元酵素阻害剤：フェンヘキサミド；フェンピラザミン；
　（ｄ）ステロール生合成系のスクワレンエポキシダーゼ阻害剤：ピリブチカルブ；ナフチフィン、テルビナフィン。 (7) cell membrane sterol biosynthesis inhibitors:
(a) C14 Demethylation Inhibitors in Sterol Biosynthesis: Trifolin; Pyrifenox, Pyrisoxazole; Fenarimol, Flurprimidol, Nuarimol; Imazalil, Imazalil Sulfate, Oxpoconazole, Pefurazoate, Prochloraz, Triflumizole , biniconazole; azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole, mefen trifluconazole;
(b) inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperaline; spiroxamine;
(c) 3-ketoreductase inhibitors in C4 demethylation of sterol biosynthesis: fenhexamide; fenpyrazamine;
(d) Squalene epoxidase inhibitors of the sterol biosynthesis system: piributicarb; naftifine, terbinafine.
（８）細胞壁合成阻害剤：
　（ａ）トレハラーゼ阻害剤：バリダマイシン；
　（ｂ）キチン合成酵素阻害剤：ポリオキシン、ポリオクソリム；
　（ｃ）セルロース合成酵素阻害剤：ジメトモルフ、フルモルフ、ピリモルフ；ベンチアバリカルブ、イプロバリカルブ、バリフェナレート；マンジプロパミド。 (8) cell wall synthesis inhibitor:
(a) a trehalase inhibitor: validamycin;
(b) chitin synthase inhibitors: polyoxins, polyoxolims;
(c) cellulose synthase inhibitors: dimethomorph, flumorph, pirimorph; bentiavaricarb, iprovalicarb, valifenalate; mandipropamide.
（９）メラニン生合成阻害剤
　（ａ）メラニン生合成の還元酵素阻害剤：フサライド；ピロキロン；トリシクラゾール；
　（ｂ）メラニン生合成の脱水酵素阻害剤：カルプロパミド；ジクロシメット；フェノキサニル；
　（ｃ）メラニン生合成のポリケタイド合成阻害剤：トルプロカルブ。 (9) melanin biosynthesis inhibitors (a) reductase inhibitors of melanin biosynthesis: fthalide; pyroquilone; tricyclazole;
(b) dehydratase inhibitors of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl;
(c) polyketide synthesis inhibitor of melanin biosynthesis: tolprocarb.
（１０）宿主植物の抵抗性誘導剤：
　（ａ）サリチル酸合成経路に作用する剤：アシベンゾラル－Ｓ－メチル；
　（ｂ）その他：プロベナゾール、チアジニル、イソチアニル、ジクロベンチアゾクス、イプフェントリフルコナゾール、ラミナリン、オオイタドリ抽出液。 (10) host plant resistance inducer:
(a) an agent acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: Probenazole, tiazinyl, isotianil, diclobentiazox, ipfentrifluconazole, laminarin, Oitadori extract.
（１１）作用性が不明な剤：シモキサニル、ホセチルアルミニウム、リン酸（リン酸塩）、テクロフタラム、トリアゾキシド、フルスルファミド、ジクロメジン、メタスルホカルブ、シフルフェナミド、メトラフェノン、ピリオフェノン、ドジン、ドジン遊離塩基、フルチアニル。 (11) Agents of unknown activity: cymoxanil, fosetylaluminum, phosphoric acid (phosphate), tecloftalam, triazoxide, fursulfamide, diclomedine, metasulfocarb, cyflufenamide, metrafenone, pyriophenone, dodine, dodine free base, flutianil.
（１２）多作用点を有する剤：銅（銅塩）、ボルドー液、水酸化銅、銅ナフタレート、酸化銅、オキシ塩化銅、硫酸銅、硫黄、硫黄製品、多硫化カルシウム；ファーバム、マンコゼブ、マネブ、マンカッパー、メチラム、ポリカーバメート、プロピネブ、チラム、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；グアザチン、グアザチンアセテート、イミノクタジン酢酸塩（iminoctadine triacetate）、イミノクタジンアルベシル酸塩（iminoctadine trialbesilate）；アニラジン；ジチアノン；キノメチオネート；フルオルイミド。 (12) agents with multiple sites of action: copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; mannkapper, metiram, polycarbamate, propineb, thiram, zineb, ziram; captan, captafol, folpet; chlorothalonil; silates (iminoctadine trialbesilate); anilazine; dithianone; quinomethionate; fluorimide.
（１３）その他の剤：ＤＢＥＤＣ、フルオロフォルペット、ビス（８－キノリノラト）銅（II）、プロパミジン、クロロピクリン、シプロフラム、アグロバクテリウム、ベトキサジン、ジフェニルアミン、メチルイソチアネート（ＭＩＴＣ）、ミルデオマイシン、カプサイシン、クフラネブ、シプロスルファミド、ダゾメット、デバカルブ、ジクロロフェン、ジフェンゾクワット、ジフェンゾクワットメチルスルホネート、フルメトベル、ホセチルカルシウム、ホセチルナトリウム、イルママイシン、ナタマイシン、ニトロタールイソプロピル、オキサモカルブ、ピロールニトリン、テブフロキン、トルニファニド、ザリラミド、アルゴフェーズ（Algophase）、アミカルチアゾール（Amicarthiazol）、オキサチアピプロリン（Oxathiapiprolin）、フルオキサピプロリン（fluoxapiprolin）、メチラム亜鉛、ベンチアゾール、トリクラミド、ユニコナゾール、オキシフェンチイン（Oxyfenthiin）、ピカルブトラゾクス（Picarbutrazox）、キノフメリン（Quinofumelin）、フロリルピコキサミド（Florylpicoxamid）、ピラプロポイン（Pyrapropoyne）、フルインダピル（Fluindapyr）、アミノピリフェン（Aminopyrifen）、ピリダクロメチル（pyridachlomethyl）、イプフルフェノキン（ipflufenoquin）、ジピメチトロン。 (13) Other agents: DBEDC, fluorofolpet, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, ciproflam, agrobacterium, betoxazine, diphenylamine, methylisocyanate (MITC), mildeomycin , capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methylsulfonate, flumetovel, fosetyl calcium, fosetyl sodium, irmamycin, natamycin, nitrothal isopropyl, oxamocarb, pyrrole nitri Tebufloquine, Tolnifanide, Zariramide, Algophase, Amicarthiazol, Oxathiapiprolin, Fluoxapiprolin, Zinc Methiram, Benthazole, Triclamide, Uniconazole, Oxyfenthin (Oxyfenthiin), Picarbutrazox, Quinofumelin, Florylpicoxamid, Pyrapropoyne, Fluindapyr, Aminopyrifen, Pyridachlomethyl, ipflufenoquin, dipimethitron.
（１４）複数の作用機構を有する生物農薬／生物由来の農薬：ハウチワマメ苗木の子葉からの抽出物（extract from the cotyledons of lupine plantlets）；Swinglea glutinosa からの抽出物 (extract from Swinglea glutinosa)；ゴセイカユプテ（ティーツリー）の抽出物(extract from Melaleuca alternifolia　(tea tree oil))；植物油類（混合物）（plant oils (mixtures)）:オイゲノール（eugenol）、ゲラニオール（geraniol）、チモール（thymol）。 (14) Biological/biological pesticides with multiple mechanisms of action: extract from the cotyledons of lupine plantlets; extract from Swinglea glutinosa; (tea tree) extract from Melaleuca alternifolia (tea tree oil); plant oils (mixtures): eugenol, geraniol, thymol.
（１５）複数の作用機構を有する生物農薬／生物由来の農薬：トリコデルマ・アトロビリデ I-1237株（Trichoderma atroviride strain I-1237）、トリコデルマ・アトロビリデ LU132株（Trichoderma atroviride strain LU132）、トリコデルマ・アトロビリデ SC1株（Trichoderma atroviride strain SC1）、トリコデルマ・アトロビリデ SKT-1株（Trichoderma atroviride strain SKT-1）、トリコデルマ・アトロビリデ 77B株（Trichoderma atroviride strain 77B）；
トリコデルマ・アスペレルム T34 株(Trichoderma asperellum strain T34)、トリコデルマ・アスペレルムkd株（Trichoderma asperellum strain kd）；
トリコデルマ・ハルチアナム　T-22 株(Trichoderma harzianum strain T-22)；
トリコデルマ・ ビレンスG-41株（Trichoderma virens　strain G-41）；
グリオクラディウム・カテナラタム J1446 株(Gliocladium catenulatum strain J1446)；
クロノスタキス・ロゼアCR-7株（Clonostachys rosea strain CR-7）；
コニオチリウム・ミニタンスCON/M/91-08株（Coniothyrium minitans strain CON/M/91-08）；
タラロマイセス・ フラバス SAY-Y-94-01 株(Talaromyces flavus strain SAY-Y-94-01)；
サッカロマイセス・セレビシエLAS02株(Saccharomyces cerevisae strain LAS02)；
バチルス・アミロリクエファシエンスQST713 株（Bacillus amyloliquefaciens strain QST713）、バチルス・アミロリクエファシエンスFZB24 株（Bacillus amyloliquefaciens strain FZB24）、バチルス・アミロリクエファシエンスMBI600 株（Bacillus amyloliquefaciens strain MBI600）、バチルス・アミロリクエファシエンスD747 株（Bacillus amyloliquefaciens strain D747）、バチルス・アミロリクエファシエンスF727 株（Bacillus amyloliquefaciens strain F727）、バチルス・アミロリクエファシエンスAT-332 株（Bacillus amyloliquefaciens strain AT-332）；
バチルス・ズブチリスAFS032321 株(Bacillus subtilis strain AFS032321) 、バチルス・ズブチリスY1336 株(Bacillus subtilis strain Y1336)、バチルス・ズブチリスHAI-0404 株(Bacillus subtilis strain HAI-0404)；
シュードモナス・クロロファフィスＡＦＳ 009 株（Pseudomonas chlororaphis　strain AFS009）；
ストレプトミセス・グリセオビリデス K61 株(Streptomyces griseovirides strain K61)；
ストレプトミセス・リディクス ＷＹＥＣ 108株（Streptomyces lydicus strain WYEC108）。 (15) Biological pesticides/biological pesticides with multiple mechanisms of action: Trichoderma atroviride strain I-1237, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1 (Trichoderma atroviride strain SC1), Trichoderma atroviride strain SKT-1 strain (Trichoderma atroviride strain SKT-1), Trichoderma atroviride strain 77B strain (Trichoderma atroviride strain 77B);
Trichoderma asperellum strain T34, Trichoderma asperellum strain kd;
Trichoderma harzianum T-22 strain (Trichoderma harzianum strain T-22);
Trichoderma virens strain G-41;
Gliocladium catenulatum J1446 strain (Gliocladium catenulatum strain J1446);
Clonostachys rosea strain CR-7;
Coniothyrium minitans strain CON/M/91-08;
Talaromyces flavus strain SAY-Y-94-01 (Talaromyces flavus strain SAY-Y-94-01);
Saccharomyces cerevisiae LAS02 strain (Saccharomyces cerevisae strain LAS02);
Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain MBI600 Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332 (Bacillus amyloliquefaciens strain AT-332);
Bacillus subtilis strain AFS032321 strain (Bacillus subtilis strain AFS032321), Bacillus subtilis strain Y1336 strain (Bacillus subtilis strain Y1336), Bacillus subtilis strain HAI-0404 strain (Bacillus subtilis strain HAI-0404);
Pseudomonas chlororaphis AFS 009 strain (Pseudomonas chlororaphis strain AFS009);
Streptomyces griseovirides K61 strain (Streptomyces griseovirides strain K61);
Streptomyces lydicus strain WYEC 108 (Streptomyces lydicus strain WYEC108).
　本発明の農園芸用殺菌剤または殺線虫剤と混用または併用することができる、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、駆虫剤などの具体例を以下に示す。
（１Ａ）アセチルコリンエステラーゼ（AChE）阻害剤（カーバメート系）：
　アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、ブトカルボキシム、ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フェノブカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メチオカルブ、メソミル、メトルカルブ、オキサミル、ピリミカーブ、プロポキスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、ＸＭＣ、キシリルカルブ。 Specific examples of insecticides/miticides, nematicides, soil pesticides, anthelmintics, etc. that can be mixed or used together with the agricultural and horticultural fungicide or nematicide of the present invention are shown below.
(1A) Acetylcholinesterase (AChE) inhibitor (carbamate):
alanicarb, aldicarb, bendiocarb, benfuracarb, butocaboxim, butoxycarboxim, carbaryl, carbofuran, carbosulphan, ethiophenecarb, phenocarb, formethanate, furatiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, Thiophanox, triazamate, trimetacarb, XMC, xylylcarb.
（１Ｂ）アセチルコリンエステラーゼ（AChE）阻害剤（有機リン系）：
　アセフェート、アザメチホス、アジンホスエチル、アジンホスメチル、カズサホス、クロレトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホスメチル、クマホス、シアノホス、ジメトン-S-メチル、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジメチルビンホス、ジスルホトン、ＥＰＮ、エチオン、エトプロホス、ファンフル、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イミシアホス、イソフェンホス、イソプロピル=O-(メトキシアミノチオホスホリル)サリチラート、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレッド、オメトエート、オキシジメトンメチル、パラチオン、パラチオンメチル、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホスメチル、プロフェノホス、プロペタムホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリムホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン。 (1B) Acetylcholinesterase (AChE) inhibitors (organophosphorus):
Acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, cassafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, dimethone-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfotone, EPN, Ethion, Etprophos, Fanfur, Fenamiphos, Fenitrothion, Fenthion, Hostthiazate, Heptenophos, Imisiaphos, Isofenphos, Isopropyl O-(methoxyaminothiophosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Nared, Omethoate, oxydimethone methyl, parathion, parathion methyl, phenthoate, folate, fosalone, phosmet, phosphamidone, phoxime, pirimiphos methyl, propenophos, propetamphos, prothiophos, pyraclofos, pyridafenthion, quinarphos, sulfotep, tebpyrimphos, temefos, terbufos, tetrachlorbinphos, Thiometone, triazophos, trichlorfon, vamidothione.
（２）GABA作動性塩化物イオン(塩素イオン)チャネルブロッカー：
　クロルデン、エンドスルファン；エチプロール、フィプロニル。
　フルフィプロル。
（３Ａ）ナトリウムチャネルモジュレーター（ピレスロイド系）：
　アクリナトリン、アレスリン、d-シス-トランス-アレスリン、d-トランス-アレスリン、ビフェントリン、ビオアレスリン、ビオアレスリン-S-シクロペンテニル-異性体、ビオレスメトリン、シクロプロトリン、シフルトリン、β-シフルトリン、シハロトリン、λ-シハロトリン、γ-シハロトリン、シペルメトリン、α-シペルメトリン、β-シペルメトリン、θ-シペルメトリン、ζ-シペルメトリン、シフェノトリン[(1R)-トランス異性体]、デルタメトリン、エンペントリン[(EZ)-(1R)-異性体]、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、τ-フルバリネート、ハルフェンプロックス、イミプリトリン、カデスリン、ペルメトリン、フェノトリン[(1R)-トランス異性体]、プラレトリン、ピレトリン、レスメトリン、シラフルオフェン、テフルトリン、テトラメスリン、テトラメスリン[(1R)-異性体]、トラロメトリン、トランスフルトリン。
　κ-ビフェントリン、クロロプラレスリン、ヘプタフルスリン、メペルフルスリン、ε-メトフルトリン、モンフルオロトリン、ε-モンフルオロトリン、κ-テフルトリン、テトラメチルフルスリン；ビオエタノメトリン。
（３Ｂ）ナトリウムチャネルモジュレーター（ＤＤＴ類）：
　ＤＤＴ、メトキシクロル。 (2) GABAergic chloride ion (chloride ion) channel blockers:
Chlordane, Endosulfan; Ethiprole, Fipronil.
Flufiprol.
(3A) Sodium channel modulators (pyrethroids):
Acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empentrin [(EZ)-( 1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprithrin, cadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrin, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin.
κ-Bifenthrin, Chloroprathrin, Heptafluthrin, Meperfluthrin, ε-Metofluthrin, Monfluorothrin, ε-Monfluorothrin, κ-Tefluthrin, Tetramethylfluthrin; Bioethanomethrin.
(3B) Sodium channel modulators (DDTs):
DDT, methoxychlor;
（４）ニコチン性アセチルコリン受容体(nAChR)競合的モジュレーター：
　アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム；ニコチン；スルホキサフロル；フルピラジフロン；トリフルメゾピリム。
　ジクロロメゾチアズ、フルピリミン。
（５）ニコチン性アセチルコリン受容体(nAChR)アロステリックモジュレーター：
　スピネトラム、スピノサド。
（６）グルタミン酸作動性塩化物イオン(塩素イオン)チャネル(GluCl) アロステリックモジュレーター：
　アバメクチン、エマメクチン、エマメクチン安息香酸塩、レピメクチン、ミルベメクチン。
　ドラメクチン、エプリノメクチン、イベルメクチン、モキシデクチン、セラメクチン。
（７）幼若ホルモン類似剤：
　ヒドロプレン、キノプレン、メトプレン；フェノキシカルブ；ピリプロキシフェン。
（８）その他の非特異的(マルチサイト)阻害剤：
　臭化メチル、ハロゲン化アルキル類；クロルピクリン；弗化アルミニウムナトリウム、フッ化スルフリル；ホウ砂、ホウ酸、オクタホウ酸ニナトリウム塩、ホウ酸ナトリウム塩、メタホウ酸ナトリウム塩；吐酒石；ダゾメット、メタム、メタムカリウム塩、メタムナトリウム塩。
（９）弦音器官TRPVチャネルモジュレーター：
　ピメトロジン、ピリフルキナゾン；アフィドピロペン。 (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators:
Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; Nicotine; Sulfoxaflor; Flupyradifuron; Triflumesopyrim.
Dichloromesotiaz, flupyrimine.
(5) Nicotinic Acetylcholine Receptor (nAChR) Allosteric Modulators:
spinetoram, spinosad.
(6) Glutamatergic chloride (chloride) channel (GluCl) allosteric modulators:
Abamectin, Emamectin, Emamectin Benzoate, Lepimectin, Milbemectin.
Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.
(7) juvenile hormone-like agents:
Hydroprene, Quinoprene, Methoprene; Fenoxycarb; Pyriproxyfen.
(8) Other non-specific (multi-site) inhibitors:
Methyl bromide, alkyl halides; chloropicrin; sodium aluminum fluoride, sulfuryl fluoride; borax, boric acid, disodium octaborate, sodium borate, sodium metaborate; tartar emetic; dazomet, metam, Metam potassium salt, metam sodium salt.
(9) String tone organ TRPV channel modulators:
pymetrozine, pyrifluquinazone; aphidopyropene.
（１０）ダニ類成長阻害剤：
　クロフェンテジン、ジフロビダジン、ヘキシチアゾクス；エトキサゾール。
（１１）微生物由来昆虫中腸内膜破壊剤：
　B.t. subsp. israelensis、B.t. subsp. aizawai、B.t. subsp. kurstaki、B.t. subsp. tenebrionis；B.t.作物に含まれるタンパク質：Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1；Bacillus sphaericus。
（１２）ミトコンドリアATP合成酵素阻害剤：
　ジアフェンチウロン；アゾシクロチン、シヘキサチン、酸化フェンブタスズ；プロパルギット；テトラジホン。
（１３）プロトン勾配を撹乱する酸化的リン酸化脱共役剤：
　クロルフェナピル、ＤＮＯＣ、スルフルミド。
（１４）ニコチン性アセチルコリン受容体(nAChR)チャネルブロッカー：
　ベンスルタップ、カルタップ塩酸塩、チオシクラム、チオスルタップ－ナトリウム塩。
（１５）キチン生合成阻害剤、タイプ０：
　ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、トリフルムロン。
（１６）キチン生合成阻害剤、タイプ１：
　ブプロフェジン。
（１７）脱皮阻害剤：
　シロマジン。
（１８）脱皮ホルモン(エクダイソン)受容体アゴニスト：
　クロマフェノジド、ハロフェノジド、メトキシフェノジド、テブフェノジド。
（１９）オクトパミン受容体アゴニスト：
　アミトラズ。 (10) Mites growth inhibitor:
Clofentezine, Diflovidazine, Hexythiazox; Etoxazole.
(11) Microorganism-derived insect midgut lining-disrupting agent:
israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. Bacillus sphaericus.
(12) Mitochondrial ATP synthase inhibitor:
diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide; propargite; tetradifon.
(13) Oxidative phosphorylation uncouplers that perturb the proton gradient:
Chlorfenapyr, DNOC, sulflumide.
(14) Nicotinic Acetylcholine Receptor (nAChR) Channel Blockers:
bensultap, cartap hydrochloride, thiocyclam, thiosultap-sodium salt.
(15) Chitin biosynthesis inhibitor, type 0:
bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron.
(16) chitin biosynthesis inhibitor, type 1:
buprofezin.
(17) molting inhibitor:
Cyromazine.
(18) molting hormone (ecdysone) receptor agonists:
Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.
(19) Octopamine receptor agonists:
Amitraz.
（２０）ミトコンドリア電子伝達系複合体III阻害剤：
　ヒドラメチルノン；アセキノシル；フルアクリピリム；ビフェナゼート。
（２１）ミトコンドリア電子伝達系複合体Ｉ阻害剤(METI)：
　フェナザキン、フェンピロキシメート、ピリダベン、ピリミジフェン、テブフェンピラド、トルフェンピラド；ロテノン。
（２２）電位依存性ナトリウムチャネルブロッカー：
　インドキサカルブ；メタフルミゾン。
（２３）アセチルCoAカルボキシラーゼ阻害剤：
　スピロジクロフェン、スピロメシフェン、スピロテトラマト。
　スピロピジオン。
（２４）ミトコンドリア電子伝達系複合体IV阻害剤：
　リン化アルミニウム、リン化カルシウム、リン化亜鉛、ホスフィン；シアン化カルシウム、シアン化ナトリウム、シアン化カリウム。
（２５）ミトコンドリア電子伝達系複合体II阻害剤：
　シエノピラフェン、シフルメトフェン；ピフルブミド。
（２８）リアノジン受容体モジュレーター：
　クロラントラニリプロール、シアントラニリプロール、シクラニリプロール、フルベンジアミド。
　シハロジアミド、テトラクロラントラニリプロール、テトラニリプロール。
（２９）弦音器官モジュレーター 標的部位未特定：
　フロニカミド。
（３０）ＧＡＢＡ作動性塩化物イオン(塩素イオン)チャネルアロステリックモジュレーター：
　ブロフラニリド、フルキサメタミド。
　イソシクロセラム；アフォキソラネル、フルララネル、ロチネラル、サロラネル。
その他の殺虫剤、殺ダニ剤：
　アザジラクチン、ベンゾキシメート、ブロモプロピレート、キノメチオナート、ジコホル、石灰硫黄合剤、マンコゼブ、ピリダリル、硫黄。
　アシノナピル、ベンズピリモキサン、フロメトキン、フルヘキサホン、オキサゾスルフィル、チクロピラゾフロル。 (20) mitochondrial electron transport chain complex III inhibitor:
hydramethylnon; acequinosyl; fluacrypyrim; bifenazate.
(21) mitochondrial electron transport chain complex I inhibitor (METI):
Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad; Rotenone.
(22) voltage-gated sodium channel blockers:
indoxacarb; metaflumizone.
(23) Acetyl-CoA carboxylase inhibitors:
Spirodiclofen, spiromesifen, spirotetramat.
spiropidion.
(24) mitochondrial electron transport chain complex IV inhibitor:
Aluminum phosphide, calcium phosphide, zinc phosphide, phosphine; calcium cyanide, sodium cyanide, potassium cyanide.
(25) mitochondrial electron transport chain complex II inhibitor:
cyenopyrafen, cyflumetofen; piflubumide.
(28) ryanodine receptor modulators:
Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Flubendiamide.
Cyhalodiamide, tetrachlorane traniliprole, tetraniliprole.
(29) Chordotome modulator Target site unspecified:
flonicamid.
(30) GABAergic chloride ion (chloride) channel allosteric modulators:
Brofuranilide, Fluxametamide.
Isocycloseram; afoxolaner, fluralaner, rotineral, sarolaner.
Other insecticides and acaricides:
Azadirachtin, benzoximate, bromopropylate, quinomethionate, dicofol, lime-sulfur mixture, mancozeb, pyridalyl, sulfur.
Acinonapyr, benzpyrimoxane, flometoquine, fluhexafone, oxazosulfil, ticlopyrazofrole.
　駆虫剤：
　（ａ）ベンズイミダゾール系：フェンベンダゾール、アルベンダゾール、トリクラベンダゾール、オキシベンダゾール、メベンダゾール、オクスフェンダゾール、パーベンダゾール、フルベンダゾール；フェバンテル、ネトビミン、チオファネート；チアベンダゾール、カンベンダゾール；
　（ｂ）サリチルアニリド系：クロサンテル、オキシクロザニド、ラフォキサニド、ニクロサミド；
　（ｃ）置換フェノール系：ニトロキシニル、ニトロスカネート；
　（ｄ）ピリミジン系：ピランテル、モランテル；
　（ｅ）イミダゾチアゾール系：レバミソール、テトラミソール；
　（ｆ）テトラヒドロピリミジン系：プラジカンテル、エプシプランテル；
　（ｇ）その他の駆虫薬：シクロジエン、リアニア、クロルスロン、メトロニダゾール、デミジトラズ；ピペラジン、ジエチルカルバマジン、ジクロロフェン、モネパンテル、トリベンジミジン、アミダンテル；チアセタルサミド、メラルソミン、アルセナマイド。 Anthelmintic:
(a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimine, thiophanate; thiabendazole, cambendazole;
(b) Salicylanilides: Closantel, Oxyclozanide, Rafoxanide, Niclosamide;
(c) substituted phenolics: nitroxynil, nitroscanate;
(d) pyrimidine series: pyrantel, morantel;
(e) imidazothiazoles: levamisole, tetramisole;
(f) tetrahydropyrimidines: praziquantel, epsiprantel;
(g) Other anthelmintics: cyclodiene, liania, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel; thiacetarsamide, melarsomine, arsenamide.
　本発明の農園芸用殺菌剤または殺線虫剤と混用または併用することができる、植物調節剤の具体例を以下に示す。
　アブシジン酸、カイネチン、ベンジルアミノプリン、１，３－ジフェニルウレア、ホルクロルフェヌロン、チジアズロン、クロルフェヌロン、ジヒドロゼアチン、ジベレリンＡ、ジベレリンＡ４、ジベレリンＡ７、ジベレリンＡ３、１－メチルシクロプロパン、Ｎ－アセチルアミノエトキシビニルグリシン(別名：アビグリシン)、アミノオキシ酢酸、硝酸銀、塩化コバルト、ＩＡＡ、４－ＣＰＡ、クロプロップ、２，４－Ｄ、ＭＣＰＢ、インドール－３－酪酸、ジクロルプロップ、フェノチオール、１－ナフチルアセトアミド、エチクロゼート、クロキシホナック、マレイン酸ヒドラジド、２，３，５－トリヨード安息香酸、サリチル酸、サリチル酸メチル、(-)－ジャスモン酸、ジャスモン酸メチル、(+)－ストリゴール、(+)－デオキシストリゴール、(+)－オロバンコール、(+)－ソルゴラクトン、４－オキソ－４－(２－フェニルエチル)アミノ酪酸；エテホン、クロルメコート、メピコートクロリド、ベンジルアデニン、５－アミノレブリン酸。 Specific examples of plant regulators that can be mixed or used together with the agricultural and horticultural fungicide or nematicide of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, horchlorfenurone, thidiazuron, chlorfenurone, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -naphthylacetamide, ethiclozate, cloxyhonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+) -deoxystrigol, (+)-olobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid; ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid.
〔製剤処方〕
　本発明の農園芸用殺菌剤または殺線虫剤は、本発明の化合物（Ｉ）やその塩のほか、他の有効成分や農園芸学的に許容される製剤化のための補助成分（たとえば、無機担体、有機担体、界面活性剤、溶媒など）を添加することができる。
　本発明の農園芸用殺菌剤または殺線虫剤は、剤形によって特に限定されない。たとえば、水和剤、乳剤、粉剤、粒剤、水溶剤、懸濁剤、顆粒水和剤、錠剤などの剤形を挙げることができる。製剤への調製方法は、特に制限されず、剤形に応じて公知の調製方法を採用することができる。
　以下に、製剤実施例を若干示す。なお、以下に示す製剤処方は単なる例示であり、本発明の主旨に反しない範囲で修正することができ、本発明は以下の製剤実施例によって何ら制限されるものではない。「部」は特段の断りが無い限り「重量部」を意味する。 [Formulation formulation]
The agricultural and horticultural fungicide or nematicide of the present invention includes the compound (I) of the present invention and a salt thereof, other active ingredients and agricultural and horticulturally acceptable auxiliary ingredients for formulation (for example, , inorganic carriers, organic carriers, surfactants, solvents, etc.) can be added.
The agricultural and horticultural fungicide or nematicide of the present invention is not particularly limited by its dosage form. For example, dosage forms such as wettable powders, emulsions, powders, granules, aqueous solutions, suspensions, wettable powders, and tablets can be mentioned. The preparation method for the formulation is not particularly limited, and a known preparation method can be adopted depending on the dosage form.
Some formulation examples are shown below. The formulation shown below is merely an example, and can be modified within the scope of the present invention, and the present invention is not limited by the following formulation examples. "Parts" means "parts by weight" unless otherwise specified.
（製剤例１：水和剤）
　本発明の含窒素ヘテロアリール化合物４０部、珪藻土５３部、高級アルコール硫酸エステル４部およびアルキルナフタレンスルホン酸塩３部を均一に混合して微細に粉砕して、有効成分４０％の水和剤を得る。
（製剤例２：乳剤）
　本発明の含窒素ヘテロアリール化合物３０部、キシレン３３部、ジメチルホルムアミド３０部およびポリオキシエチレンアルキルアリルエーテル７部を混合し溶解させて、有効成分３０％の乳剤を得る。
（製剤例３：粒剤）
　本発明の含窒素ヘテロアリール化合物５部、タルク４０部、クレー３８部、ベントナイト１０部およびアルキル硫酸ソーダ７部を均一に混合し、微細に粉砕し、その後、粒子直径０．５～１．０ｍｍに造粒して有効成分５％の粒剤を得る。
（製剤例４：粒剤）
　本発明の含窒素ヘテロアリール化合物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部およびリン酸カリウム１部を均一に混合し、粉砕した。これに水を加えてよく練り合せ、その後、造粒し、乾燥させて、有効成分５％の粒剤を得る。
（製剤例５：懸濁剤）
　本発明の含窒素ヘテロアリール化合物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部および水７３．８部を混合し、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。
（製剤例６：顆粒水和剤）
　本発明の含窒素ヘテロアリール化合物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部および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、次いで乾燥させて有効成分４０％の顆粒水和剤を得る。 (Formulation Example 1: wettable powder)
40 parts of the nitrogen-containing heteroaryl compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder containing 40% of the active ingredient. obtain.
(Formulation Example 2: Emulsion)
30 parts of the nitrogen-containing heteroaryl compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide and 7 parts of polyoxyethylene alkylallyl ether are mixed and dissolved to obtain an emulsion containing 30% active ingredient.
(Formulation Example 3: Granules)
5 parts of the nitrogen-containing heteroaryl compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then the particle diameter is 0.5 to 1.0 mm. to obtain granules containing 5% of the active ingredient.
(Formulation Example 4: Granules)
5 parts of the nitrogen-containing heteroaryl compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt and 1 part of potassium phosphate were uniformly mixed and ground. Water is added to this and the mixture is thoroughly kneaded, then granulated and dried to obtain granules containing 5% of the active ingredient.
(Formulation Example 5: Suspension agent)
10 parts of the nitrogen-containing heteroaryl compound of the present invention, 4 parts of polyoxyethylene alkylallyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water are mixed and the particle size is 3. Wet mill to submicron size to obtain a suspension of 10% active ingredient.
(Formulation Example 6: Granule wettable powder)
40 parts of the nitrogen-containing heteroaryl compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzenesulfonate, 8 parts of sodium ligninsulfonate and 5 parts of formaldehyde condensate of sodium alkylbenzenesulfonate are uniformly mixed. After mixing and pulverizing finely, an appropriate amount of water is added and kneaded to form clay. The clay is granulated and then dried to obtain water dispersible granules containing 40% active ingredient.
〔医療用・動物用（獣医療用）抗真菌剤〕
　本発明の含窒素ヘテロアリール化合物は、人または動物に感染する有害な病原菌、特に真菌を防除対象とした予防薬、治療薬として用いることができる。
　本発明の医療用・動物用抗真菌剤は、化合物（Ｉ）およびその塩から選ばれる少なくともひとつを有効成分として含有するものである。本発明の医療用抗真菌剤に含まれる化合物（Ｉ）またはその塩の量は、抗真菌効果を示す限りにおいて特に制限されない。 [Medical and veterinary (veterinary) antifungal agents]
The nitrogen-containing heteroaryl compound of the present invention can be used as a prophylactic or therapeutic agent for controlling harmful pathogens, especially fungi, that infect humans or animals.
The medical/veterinary antifungal agent of the present invention contains at least one selected from compound (I) and salts thereof as an active ingredient. The amount of compound (I) or a salt thereof contained in the medical antifungal agent of the present invention is not particularly limited as long as the antifungal effect is exhibited.
　本明細書における「動物」とは、愛玩動物や家畜・家禽、動物園や水族館等で飼育される展示動物、捕獲した野生動物、さらには研究・実験動物等の脊椎動物（V e r t e b r a t a）を意味する。 The term "animal" as used herein refers to pets, livestock and poultry, animals raised in zoos and aquariums, captured wild animals, and vertebrates such as research and experimental animals (Vertebrates) means r a t a).
　例えば、以下の動物が挙げられるが、動物の具体例はこれらのみに限定されるものではない。
　ヒツジ、ヤギ、ブタ、ウマ、ウシ、スイギュウ、ロバ、ラバ、ラクダ、ラマ、アルパカ、イノシシ、トナカイ、シカ、ミンク、ゾウ、クマ、カンガルー、キツネ、イヌ、ネコ、リス、ウサギ、マウス、ラット、モルモット、ハムスター、サル、フェレット等の哺乳類。
　ハト、インコ、オウム、ブンチョウ、ジュウシマツ、カナリア、ニワトリ、アヒル、シチメンチョウ、カモ、キジ、クジャク、ダチョウ、ハクチョウ、スズメ、ウズラ、フクロウ、ワシ、タカ、ウミウなどの鳥類。
　カメレオン、イグアナ、トカゲ、ヘビ、カメ、ワニ、ヤモリなどの爬虫類。
　カエル、イモリなどの両生類。
　コイ、キンギョ、メダカ、熱帯魚、ブリ・ハマチ、タイ、カンパチ、サケ、サバ、スズキ、クエ、マグロ、アジ、ヒラメ、フグなどの魚類。 Examples include the following animals, but specific examples of animals are not limited to these.
sheep, goat, pig, horse, cow, buffalo, donkey, mule, camel, llama, alpaca, wild boar, reindeer, deer, mink, elephant, bear, kangaroo, fox, dog, cat, squirrel, rabbit, mouse, rat, Mammals such as guinea pigs, hamsters, monkeys and ferrets.
Birds such as pigeons, parakeets, parrots, sparrows, marigolds, canaries, chickens, ducks, turkeys, ducks, pheasants, peacocks, ostriches, swans, sparrows, quail, owls, eagles, hawks, and cormorants.
Reptiles such as chameleons, iguanas, lizards, snakes, turtles, crocodiles and geckos.
Amphibians such as frogs and newts.
Fish such as carp, goldfish, killifish, tropical fish, yellowtail, yellowtail, sea bream, amberjack, salmon, mackerel, sea bass, longtooth grouper, tuna, horse mackerel, flounder, and blowfish.
　本発明の医療用・動物用抗真菌剤の適用が可能な病原菌として、真菌（カビ）の例を以下に示す。なお、具体例はこれらのみに限定されるものではない。
　例えば、absidia corymbiferaなどのAbsidia属；Acremonium属；Alternaria alternataなどのAlternaria属；Aspergillus flavus、Aspergillus fumigatus、Aspergillus nidulans、Aspergillus niger、Aspergillus parasiticus、Aspergillus terreusなどのAspergillus属；Bipolaris属；Blastomyces dermatitidisなどのBlastomyces属；Blumeria graminisなどのBlumeria属；Candida albicans、Candida glabrata、Candida krusei、Candida parapsilosis、Candida tropicalisなどのCandida属；Cladosporium cladosporoides、Cladosporium herbariumなどのCladosporium属；Coccidioides immitis、Coccidioides posadasiiなどのCoccidioides属；Colletotrichium trifoliiなどのColletotrichium属；Cryptococcus neoformansなどのCryptococcus属；Curvularia lunataなどのCurvularia属；Encephalitozoon cuniculiなどのEncephalitozoon属；Epicoccum nigrumなどのEpicoccum属；Epidermophyton floccosumなどのEpidermophyton属；Exophiala属；　Exserohilum rostratumなどのExserohilum属；Fusarium graminarium、Fusarium solani、Fusarium sporotrichoidesなどのFusarium属；Fonsecaea monophoraなどのFonsecaea属；　Histoplasma capsulatumなどのHistoplasma属；Leptosphaeria nodorumなどのLeptosphaeria属；　Malassezia globosaなどのMalassezia 属； Microsporum canisなどのMicrosporum属；Mycosphaerella graminicolaなどのMycosphaerella属；Neurospora属；Paecilomyces lilanicus、Paecilomyces variotiなどのPaecilomyces属；PenicilliumchrysogenumなどのPenicillium属；　Phytophthora capsici、Phytophthora infestansなどのPhytophthora属；Plasmopara viticolaなどのPlasmopara属；Pneumocystis jiroveciiなどのPneumocystis属；Pyricularia oryzaeなどのPyricularia属；Pythium ultimumなどのPythium属；Puccinia coronata、Puccinia graminisなどのPuccinia属；Rhizoctonia solaniなどのRhizoctonia属；Rhizomucor属；Fusarium apiospermum、Scedosporium prolificansなどのScedosporium属；Scopulariopsis brevicaulisなどのScopulariopsis属； Sporothrix schenckiiなどのSporothrix 属；　Talaromyces marneffeiなどのTalaromyces属、Trichophyton mentagrophytes、Trichophyton interdigitale、Trichophyton rubrum、Trichophyton tonsurans、Trichophyton verrucosumなどのTrichophyton属；Trichosporon asahii、Trichosporon beigeliiなどのTrichosporon属；Ustilago属など。
　これらの中、本発明の抗真菌剤は、Aspergillus属、Trichophyton属またはCandida属に対して好適であり、Aspergillus fumigatusまたはTrichophyton tonsuransに対して特に好適である。 Examples of fungi (molds) are shown below as pathogenic bacteria to which the medical and veterinary antifungal agent of the present invention can be applied. However, specific examples are not limited to these.
Alternaria genera such as Alternaria alternata; Aspergillus genera such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, Aspergillus parasiticus, Aspergillus terreus; Bipolaris genera; Blastomyces genera such as Blastomyces dermatitidis ; Blumeria genus such as Blumeria graminis; Candida genus such as Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, and Candida tropicalis; Cladosporium genus such as Cladosporium cladosporoides and Cladosporium herbarium; Cryptococcus genera such as Cryptococcus neoformans; Curvularia genera such as Curvularia lunata; Encephalitozoon genera such as Encephalitozoon cuniculi; Epicoccum genera such as Epicoccum nigrum; Fusarium genera, such as graminarium, Fusarium solani, Fusarium sporotrichoides; Fonsecaea genera, such as Fonsecaea monophora; Histoplasma genera, such as Histoplasma capsulatum; Leptosphaeria genera, such as Leptosphaeria nodorum; Mal Genus Malassezia such as assezia globosa; Genus Microsporum such as Microsporum canis; Genus Mycosphaerella such as Mycosphaerella graminicola; Genus Neurospora; Genus Plasmopara such as Plasmopara viticola; Genus Pneumocystis such as Pneumocystis jirovecii; Genus Pyricularia such as Pyricularia oryzae; Genus Pythium such as Pythium ultimum; Genus Puccinia such as Puccinia coronata and Puccinia graminis; Scedosporium genera such as Scedosporium prolificans; Scopulariopsis genera such as Scopulariopsis brevicaulis; Sporothrix genera such as Sporothrix schenckii; Talaromyces genera such as Talaromyces marneffei; , Trichosporon beigelii, etc.;
Among these, the antifungal agent of the present invention is suitable for Aspergillus, Trichophyton or Candida, and particularly suitable for Aspergillus fumigatus or Trichophyton tonsurans.
　本発明の医療用・動物用抗真菌剤の適用が可能な感染症として、真菌症の例を以下に示す。なお、具体例はこれらのみに限定されるものではない。 Examples of mycoses are shown below as infectious diseases to which the medical and veterinary antifungal agent of the present invention can be applied. However, specific examples are not limited to these.
　本発明の医療用・動物用抗真菌剤は、全身性真菌感染症、表在性真菌感染症などのいずれにも適用できる。真菌感染症の具体例としては、肺アスペルギルス症、全身性アスペルギルス症（骨髄受容者またはAIDS患者などの免疫抑制患者において発症しやすい）などのアスペルギルス（Aspergillus）症、全身性カンジダ症などのカンジダ（Candida）症、クリプトコッカス（Cryptococcus）髄膜炎、鼻脳型ムコール症（rhinocerebral mucomycosis）、肺ムコール症、ブラストミセス症、ヒストプラスマ症、コクシジオイデス症（coccidiomycosis）、パラコクシジオイデス症（paracoccidiomycosis）、ロボ真菌症、角膜真菌症、スポロトリクム症、クロモブラストミコーシス、クロモミコーシス、フェオフィホ真菌症、接合菌症、クリプトコッカス症、播種性スポロトリクム症、白癬（ring worm）、頭部白癬（しらくも）、体部白癬（たむし）、股部白癬（いんきん）、足白癬（水虫）、爪白癬（爪水虫）、皮膚、口、または膣のカンジダ症、マラセチア症、慢性粘膜皮膚カンジダ症、ニューモシスチス肺炎、マルネフェイ型ペニシリウム症等が挙げられる。
　また、本発明の抗真菌剤は、真菌によって引き起こされるアレルギー疾患、例えば、アレルギー性気管支肺喘息（allergic bronchopulmonary asthma）（ABPA）；喘息、鼻副鼻腔炎、または副鼻腔炎等にも適用可能である。 The medical/veterinary antifungal agent of the present invention can be applied to both systemic fungal infections and superficial fungal infections. Specific examples of fungal infections include Aspergillus diseases such as pulmonary aspergillosis, systemic aspergillosis (which is more likely to occur in immunosuppressed patients such as bone marrow recipients or AIDS patients), Candida diseases such as systemic candidiasis ( Candida disease, Cryptococcus meningitis, rhinocerebral mucomycosis, pulmonary mucormycosis, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, robomycosis, Keratomycosis, sporotrichosis, chromoblastomycosis, chromomycosis, pheophyphomycosis, zygomycosis, cryptococcosis, disseminated sporotrichosis, ring worm, tinea capitis, tinea corporis , tinea pedis (athlete's foot), tinea pedis (athlete's foot), tinea unguium (athlete's foot), candidiasis of the skin, mouth, or vagina, malassechiosis, chronic mucocutaneous candidiasis, Pneumocystis pneumoniae, and penicilliosis of the Marnefei type. be done.
In addition, the antifungal agent of the present invention can also be applied to allergic diseases caused by fungi, such as allergic bronchopulmonary asthma (ABPA); asthma, rhinosinusitis, or sinusitis. be.
　本発明の医療用・動物用抗真菌剤は、薬学的に許容される添加剤を含むことができる。添加剤は、公知の医療用薬剤において、使用されているものであれば特に制限されない。これらは、当然ながら、無菌であり、発熱性がない。また、添加剤は、抗真菌剤の剤型や投与方法などに応じて、適宜、選択することができる。 The medical/veterinary antifungal agent of the present invention can contain pharmaceutically acceptable additives. Additives are not particularly limited as long as they are used in known medical drugs. They are of course sterile and non-pyrogenic. In addition, the additive can be appropriately selected according to the dosage form and administration method of the antifungal agent.
　本発明の医療用・動物用抗真菌剤が採り得る剤型は、特に限定されず、例えば、錠剤、粉剤、粒剤、顆粒剤、カプセル剤、トローチ（飴）、ペレットなどの固体剤；シロップ、乳濁剤、懸濁剤、溶液、滴下（Pour-on)剤、点下(Spot-on)剤、などの液体剤；軟膏剤、ゲルなどの半固体調製物など；エアロゾル、蒸気などの気体剤；ナノ粒子製剤などを挙げることができる。
　本発明の医療用抗真菌剤の投与は、公知の方法で行うことができる。投与方法としては、例えば、皮下、静脈内、筋肉内、胸骨内（intrasternally）等への注入（注射）；肛門、膣などへの挿入、皮膚表面への塗布や散布、滴下などの経皮投与；口から服用などの経口投与；吸気などによる経鼻投与などを挙げることができる。 The dosage form that the medical/veterinary antifungal agent of the present invention can take is not particularly limited. , emulsions, suspensions, solutions, drops (Pour-on), spot-on, etc.; semi-solid preparations such as ointments, gels, etc.; aerosols, vapors, etc. Gaseous agents; nanoparticle formulations and the like can be mentioned.
Administration of the medical antifungal agent of the present invention can be performed by known methods. Examples of administration methods include subcutaneous, intravenous, intramuscular, intrasternal injection (injection); insertion into the anus, vagina, etc.; oral administration such as oral administration; nasal administration such as inhalation.
　経口投与用の固体剤の場合、本発明の医療用・動物用抗真菌剤に使用できる添加剤としては、シクロデキストリンまたは修飾シクロデキストリン等の溶解補助剤；ラクトース、デキストロース、サッカロース、セルロース、コーンスターチまたはジャガイモデンプン等の希釈剤；シリカ、タルク、ステアリン酸、ステアリン酸マグネシウムもしくはステアリン酸カルシウム、ポリエチレングリコール等の滑沢剤；デンプン、アラビアゴム（arabic gums）、ゼラチン、メチルセルロース、カルボキシメチルセルロースまたはポリビニルピロリドン等の結合剤；デンプン、アルギン酸、アルギン酸塩またはグリコール酸デンプンナトリウム等の脱凝集剤（disaggregating agents）；発泡性混合物（effervescing mixtures）；色素；甘味剤；レシチン、ポリソルベート、ラウリル硫酸（laurylsulphates）等の湿潤剤；または一般に医薬製剤に用いられる非毒性で薬理学的に不活性な物質等を挙げることができる。これら添加剤は、混合、造粒、打錠、糖衣、またはフィルムコーティング等の公知の方法により本発明の医療用抗真菌剤に含有させることができる。 In the case of oral solid formulations, additives that can be used in the medical and veterinary antifungal agents of the present invention include solubilizers such as cyclodextrins or modified cyclodextrins; lactose, dextrose, sucrose, cellulose, cornstarch or Diluents such as potato starch; Lubricants such as silica, talc, stearic acid, magnesium or calcium stearate, polyethylene glycol; Binding agents such as starch, arabic gums, gelatin, methylcellulose, carboxymethylcellulose or polyvinylpyrrolidone. agents; disaggregating agents such as starch, alginic acid, alginates or sodium starch glycolate; effervescing mixtures; dyes; sweeteners; Alternatively, non-toxic and pharmacologically inactive substances generally used in pharmaceutical formulations can be used. These additives can be incorporated into the medical antifungal agent of the present invention by known methods such as mixing, granulation, tableting, sugar coating, or film coating.
　経口投与用の液体剤の場合、本発明の医療用・動物用抗真菌剤に使用できる添加剤としては、シクロデキストリンまたは修飾シクロデキストリン等の溶解補助剤、サッカロースを、グリセリン、マンニトール、ソルビトール、天然ガム、寒天、アルギン酸ナトリウム、ペクチン、メチルセルロース、カルボキシメチルセルロース、またはポリビニルアルコール等を挙げることができる。 In the case of liquid formulations for oral administration, additives that can be used in the medical and veterinary antifungal agents of the present invention include solubilizers such as cyclodextrins or modified cyclodextrins, saccharose, glycerin, mannitol, sorbitol, natural gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, polyvinyl alcohol, and the like.
　筋肉内注射用の液体剤の場合、本発明の医療用・動物用抗真菌剤に使用できる添加剤としては、滅菌水、オリーブ油、オレイン酸エチル、プロピレングリコール等のグリコール類、シクロデキストリン、修飾シクロデキストリン等の溶解補助剤等を挙げることができる。さらに必要に応じて適切な量のリドカイン塩酸塩を含ませることもできる。 In the case of a liquid preparation for intramuscular injection, the additives that can be used in the medical and veterinary antifungal agent of the present invention include sterilized water, olive oil, ethyl oleate, glycols such as propylene glycol, cyclodextrin, and modified cyclodextrins. Dissolution aids such as dextrin can be used. Furthermore, an appropriate amount of lidocaine hydrochloride can be included as necessary.
　静脈注射用の液体剤の場合、本発明の医療用・動物用抗真菌剤に使用できる添加剤としては、滅菌水等の担体；シクロデキストリン、修飾シクロデキストリン等の溶解補助剤等を挙げることができる。これらは滅菌した等張生理食塩水溶液の形態で含ませることもできる。 In the case of a liquid preparation for intravenous injection, examples of additives that can be used in the medical or veterinary antifungal agent of the present invention include carriers such as sterile water; solubilizers such as cyclodextrins and modified cyclodextrins. can. They can also be included in the form of sterile isotonic saline solutions.
　本発明の医療用・動物用抗真菌剤に含有する化合物（Ｉ）またはその塩の量は、抗真菌剤の重量に対して、好ましくは８５重量％以下、より好ましくは５０重量％以下である。
　本発明の医療用・動物用抗真菌剤の用量は、投与方法、感染した真菌の種類、患者の年齢、体重、症状等に応じて適宜選択することができる。例えば、成人に対しては、経口または非経口（注射、点滴等）的投与の場合、１日に１または数回、０．１～１００ｍｇ／ｋｇ-体重にて投与することができる。
　また、本発明の医療用・動物用抗真菌剤は、化合物（Ｉ）以外の他の薬剤と組み合わせで使用することができる。 The amount of compound (I) or a salt thereof contained in the medical or veterinary antifungal agent of the present invention is preferably 85% by weight or less, more preferably 50% by weight or less, based on the weight of the antifungal agent. .
The dose of the medical/veterinary antifungal agent of the present invention can be appropriately selected according to the administration method, the type of fungi infected, the patient's age, body weight, symptoms, and the like. For example, in the case of oral or parenteral (injection, infusion, etc.) administration to adults, it can be administered at 0.1 to 100 mg/kg-body weight once or several times a day.
In addition, the medical and veterinary antifungal agents of the present invention can be used in combination with drugs other than compound (I).
　以下に合成実施例を示し、本発明をより具体的に説明する。ただし、本発明は以下の合成実施例によって何ら制限されるものではない。
〔実施例１〕
(E)-2-(3-(1-(isopropoxyimino)ethyl)-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamideの合成
（工程１）
2-(5-bromo-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamideの合成
Figure JPOXMLDOC01-appb-C000005
 5-bromopyridin-2-ol（２.０ｇ）をＮ，Ｎ－ジメチルホルムアミド（４０ｍｌ）に溶解させ、炭酸カリウム（２．６０ｇ）、2-bromo-N-isopropylpropanamide（２．９０ｇ）を加え、室温にて３時間撹拌した。反応液に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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：クロロホルム／酢酸エチル）で精製し、目的化合物３．２０ｇを得た。収率９６％。目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 7.64 (1H, s), 7.38 (1H, d, J = 9.6 Hz), 6.50 (1H, d, J = 9.6 Hz), 6.32-3.94 (3H, m ), 1.57-1.07(9H, m) Synthesis examples are shown below to describe the present invention more specifically. However, the present invention is in no way limited by the following synthesis examples.
[Example 1]
Synthesis of (E)-2-(3-(1-(isopropoxyimino)ethyl)-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide (Step 1)
Synthesis of 2-(5-bromo-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
Figure JPOXMLDOC01-appb-C000005
 5-bromopyridin-2-ol (2.0 g) was dissolved in N,N-dimethylformamide (40 ml), potassium carbonate (2.60 g) and 2-bromo-N-isopropylpropanamide (2.90 g) were added, and the mixture was stirred at room temperature. and stirred for 3 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: chloroform/ethyl acetate) to obtain 3.20 g of the desired compound. Yield 96%. 1 H-NMR of the desired product is shown below.
1 H-NMR (CDCl 3 ) δ: 7.64 (1H, s), 7.38 (1H, d, J = 9.6 Hz), 6.50 (1H, d, J = 9.6 Hz), 6.32-3.94 (3H, m ), 1.57-1.07(9H,m)
（工程２）
2-(3-bromo-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
の合成
Figure JPOXMLDOC01-appb-C000006
 2-(5-bromo-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide（０．８０ｇ）をＮ，Ｎ－ジメチルホルムアミド（２０ｍｌ）に溶解させ、1-ethynyl-2-methoxybenzene（０．６０ｇ）、トリエチルアミン（１２ｍｌ）ヨウ化銅（I）（０．０９ｇ）、ビス（トリフェニルホスフィン）パラジウム（ＩＩ）ジクロリド（０．３０ｇ）を加え、８０ °Cにて７時間撹拌した。反応液に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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：ヘキサン／酢酸エチル）で精製し、得られたものをメタノール（１２ｍｌ）に溶解させ、１０％パラジウム炭素（０．３ｇ）を加え、水素雰囲気下、室温で３時間攪拌した。反応液を濾過し、溶媒を減圧留去し得たものを塩化メチレン（７ｍｌ）に溶解させ、Ｎ－ブロモスクシンイミド（０．２３ｇ）を加え、室温にて６時間撹拌した。反応液に水を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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：ヘキサン／酢酸エチル）で精製し、目的化合物０．４２ｇを得た。収率３６％。目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 7.64-6.82 (6H, m), 6.30-2.61(7H, m), 3.79 (3H, s), 1.44-1.02(9H, m) (Step 2)
2-(3-bromo-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
Synthesis of
Figure JPOXMLDOC01-appb-C000006
 2-(5-bromo-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide (0.80 g) was dissolved in N,N-dimethylformamide (20 ml), and 1-ethynyl-2-methoxybenzene (0 .60 g), triethylamine (12 ml), copper (I) iodide (0.09 g) and bis(triphenylphosphine)palladium (II) dichloride (0.30 g) were added and stirred at 80° C. for 7 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate). was added, and the mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered, the solvent was distilled off under reduced pressure, and the residue was dissolved in methylene chloride (7 ml), N-bromosuccinimide (0.23 g) was added, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 0.42 g of the target compound. Yield 36%. 1 H-NMR of the desired product is shown below.
1 H-NMR (CDCl 3 ) δ: 7.64-6.82 (6H, m), 6.30-2.61 (7H, m), 3.79 (3H, s), 1.44-1.02 (9H, m)
(工程５)
2-(3-acetyl-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamideの合成
Figure JPOXMLDOC01-appb-C000007
 2-(3-bromo-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
（０．３２ｇ）を１，４-ジオキサン（５ｍｌ）に溶解させ、tributyl(1-ethoxyvinyl)stannane（０．３７ｇ）、ビス（トリフェニルホスフィン）パラジウム（ＩＩ）ジクロリド（０．０６ｇ）を加え、２時間加熱還流した。反応液をシリカゲルカラムクロマトグラフィー（展開溶媒：ヘキサン／酢酸エチル）で精製し、得られたものをテトラヒドロフラン（５ｍｌ）に溶解させ、４規定塩化水素水溶液（１．５ｍｌ）を加え、５０ °Cにて４時間攪拌した。反応液に水を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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：ヘキサン／酢酸エチル）で精製し、目的化合物０．２１ｇを得た。収率７１％。目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 8.06-6.82 (6H, m), 6.25-2.63(7H, m), 3.81 (3H, s), 2.67 (3H, s), 1.44-1.04(9H, m) (Step 5)
Synthesis of 2-(3-acetyl-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
Figure JPOXMLDOC01-appb-C000007
 2-(3-bromo-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
(0.32 g) was dissolved in 1,4-dioxane (5 ml), tributyl(1-ethoxyvinyl)stannane (0.37 g), bis(triphenylphosphine) palladium (II) dichloride (0.06 g) were added, It was heated to reflux for 2 hours. The reaction solution was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate), the obtained product was dissolved in tetrahydrofuran (5 ml), 4N aqueous hydrogen chloride solution (1.5 ml) was added, and the temperature was raised to 50°C. and stirred for 4 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 0.21 g of the desired compound. Yield 71%. 1 H-NMR of the desired product is shown below.
1 H-NMR (CDCl 3 ) δ: 8.06-6.82 (6H, m), 6.25-2.63(7H, m), 3.81 (3H, s), 2.67 (3H, s), 1.44-1.04(9H, m)
(工程６)
(E)-2-(3-(1-(isopropoxyimino)ethyl)-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamideの合成
Figure JPOXMLDOC01-appb-C000008
 2-(3-acetyl-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide（０．０９ｇ）をエタノール（２ｍｌ）、クロロホルム（２ｍｌ）に溶解させ、ピリジン（０．０４ｇ）、2-(aminooxy)propane hydrochloride(０．０５ｇ)を加え、室温にて１時間攪拌した。溶媒を減圧留去し、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：ヘキサン／酢酸エチル）で精製し、目的化合物０．０９ｇを得た。収率９０％得られた目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 7.40-6.82 (6H, m), 6.28-2.63(8H, m), 3.79 (3H, s), 2.18 (3H, s), 1.44-1.00(15H, m) (Step 6)
Synthesis of (E)-2-(3-(1-(isopropoxyimino)ethyl)-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide
Figure JPOXMLDOC01-appb-C000008
 2-(3-acetyl-5-(2-methoxyphenethyl)-2-oxopyridin-1(2H)-yl)-N-isopropylpropanamide (0.09 g) was dissolved in ethanol (2 ml) and chloroform (2 ml), and pyridine (0.04 g) and 2-(aminooxy)propane hydrochloride (0.05 g) were added and stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 0.09 g of the desired compound. 1 H-NMR of the desired product obtained with a yield of 90% is shown below.
1 H-NMR (CDCl 3 ) δ: 7.40-6.82 (6H, m), 6.28-2.63(8H, m), 3.79 (3H, s), 2.18 (3H, s), 1.44-1.00(15H, m)
〔実施例２〕
N-((2S)-1-(5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-((E)-1-isopropoxyimino)ethyl)-2-oxopyridin-1(2H)-yl)propan-2-yl)isobutyramideの合成
（工程１）
(E)-1-(5-bromo-2-methoxypyridin-3-yl)ethan-1-one O-isopropyl oximeの合成
Figure JPOXMLDOC01-appb-C000009
 1-(5-bromo-2-methoxypyridin-3-yl)ethan-1-one（１．０ｇ）をエタノール（１５ｍｌ）に溶解させ、2-(aminooxy)propane hydrochloride(０．５５ｇ)を加え、室温にて一晩攪拌した。溶媒を減圧留去し、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：ヘキサン／酢酸エチル）で精製し、目的化合物１．２０ｇを得た。収率９７％得られた目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 8.18-4.40 (3H, m), 3.94 (3H, s), 2.14 (3H, s), 1.27(6H, m) [Example 2]
N-((2S)-1-(5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-((E)-1-isopropoxyimino)ethyl)-2-oxopyridin-1( Synthesis of 2H)-yl)propan-2-yl)isobutyramide (step 1)
Synthesis of (E)-1-(5-bromo-2-methoxypyridin-3-yl)ethan-1-one O-isopropyl oxime
Figure JPOXMLDOC01-appb-C000009
 1-(5-bromo-2-methoxypyridin-3-yl)ethan-1-one (1.0 g) was dissolved in ethanol (15 ml), 2-(aminooxy) propane hydrochloride (0.55 g) was added, and the mixture was warmed to room temperature. and stirred overnight. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 1.20 g of the target compound. 1 H-NMR of the desired product obtained with a yield of 97% is shown below.
1 H-NMR (CDCl 3 ) δ: 8.18-4.40 (3H, m), 3.94 (3H, s), 2.14 (3H, s), 1.27(6H, m)
（工程２）
(E)-1-(5-fluoro-2-methoxyphenyl)-2-(5-(1-(isopropoxyimino)ethyl)-6-ethoxypyridin-3-yl)ethan-1-oneの合成
Figure JPOXMLDOC01-appb-C000010
 １．３Ｍリチウム（ビストリメチルシリル）アミド　テトラヒドロフラン溶液（１５ｍｌ）に１，４-ジオキサン（５ｍｌ）に1-(5-fluoro-2-methoxyphenyl)ethan-1-oneを溶解させたものを加えた。その後、トリ-t-ブチルホスフィン（０．２ｇ）とトリス（ジベンジリデンアセトン）ジパラジウム（０）（０．３５ｇ）を１，４-ジキオサン（１５ｍｌ）に溶かしたものを加え、更に(E)-1-(5-bromo-2-methoxypyridin-3-yl)ethan-1-one O-isopropyl oxime（１．８０ｇ）を１，４-ジキオサン（５ｍｌ）に溶かしたものを加え、90°Cにて２時間撹拌した。反応液に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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：ヘキサン／酢酸エチル）で精製し、目的化合物１．７５ｇを得た。収率７４％。目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 7.99-4.37 (6H, m), 4.22 (2H, s), 3.94 (3H, s), 3.93 (3H, s), 2.16 (3H, s),1.27(6H, m) (Step 2)
Synthesis of (E)-1-(5-fluoro-2-methoxyphenyl)-2-(5-(1-(isopropoxyimino)ethyl)-6-ethoxypyridin-3-yl)ethan-1-one
Figure JPOXMLDOC01-appb-C000010
 A solution obtained by dissolving 1-(5-fluoro-2-methoxyphenyl)ethan-1-one in 1,4-dioxane (5 ml) was added to a 1.3 M lithium (bistrimethylsilyl)amide tetrahydrofuran solution (15 ml). After that, a solution of tri-t-butylphosphine (0.2 g) and tris(dibenzylideneacetone) dipalladium (0) (0.35 g) dissolved in 1,4-diquiosane (15 ml) was added, and (E) A solution of -1-(5-bromo-2-methoxypyridin-3-yl)ethan-1-one O-isopropyl oxime (1.80 g) dissolved in 1,4-diquiosane (5 ml) was added, and the mixture was heated to 90°C. and stirred for 2 hours. A saturated aqueous ammonium chloride solution was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 1.75 g of the target compound. Yield 74%. 1 H-NMR of the desired product is shown below.
1 H-NMR (CDCl 3 ) δ: 7.99-4.37 (6H, m), 4.22 (2H, s), 3.94 (3H, s), 3.93 (3H, s), 2.16 (3H, s), 1.27(6H , m)
（工程３）
(E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-3-(1-(isopropoxyimino)ethyl)pyridin-2(1H)-oneの合成
Figure JPOXMLDOC01-appb-C000011
 (E)-1-(5-fluoro-2-methoxyphenyl)-2-(5-(1-(isopropoxyimino)ethyl)-6-methoxypyridin-3-yl)ethan-1-one（１．３０ｇ）をＮ，Ｎ－ジメチルホルムアミド（８ｍｌ）に溶解させ、ｐ－トルエンスルホン酸一水和物（２．５０ｇ）、塩化リチウム（０．５５ｇ）を加え、70°Cにて２時間撹拌した。反応液に水を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し得られた残渣をジエチルエーテルで洗浄し、目的化合物０．８６ｇを得た。収率６９％。目的物の1H-NMRを以下に示す。1H-NMR (DMSO-d6) δ: 7.45-4.27 (6H, m), 4.08 (2H, s), 3.90 (3H, s), 2.06 (3H, s),1.22(6H, m) (Step 3)
Synthesis of (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-3-(1-(isopropoxyimino)ethyl)pyridin-2(1H)-one
Figure JPOXMLDOC01-appb-C000011
 (E)-1-(5-fluoro-2-methoxyphenyl)-2-(5-(1-(isopropoxyimino)ethyl)-6-methoxypyridin-3-yl)ethan-1-one (1.30 g) , N-dimethylformamide (8 ml), p-toluenesulfonic acid monohydrate (2.50 g) and lithium chloride (0.55 g) were added, and the mixture was stirred at 70°C for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was washed with diethyl ether to obtain 0.86 g of the target compound. Yield 69%. 1 H-NMR of the desired product is shown below. 1H - NMR (DMSO-d6) δ: 7.45-4.27 (6H, m), 4.08 (2H, s), 3.90 (3H, s), 2.06 (3H, s), 1.22(6H, m)
（工程４）
(E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-(1-(isopropoxyimino)ethyl)pyridin-2(1H)-oneの合成
Figure JPOXMLDOC01-appb-C000012
 (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-3-(1-(isopropoxyimino)ethyl)pyridin-2(1H)-one（０．２ｇ）をメタノール（２ｍｌ）、テトラヒドロフラン（２ｍｌ）に溶解させ、氷冷下、水素化ホウ素ナトリウム（２０ｍｇ）を加え３０分撹拌した。反応液に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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）で精製し、目的化合物 ０．１５ｇを得た。収率７５％。
1H-NMR (CDCl3) δ: 7.52-2.73 (10H, m), 3.81 (3H, s), 2.22 (3H, s),1.27(6H, m) (Step 4)
Synthesis of (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-(1-(isopropoxyimino)ethyl)pyridin-2(1H)-one
Figure JPOXMLDOC01-appb-C000012
 (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-3-(1-(isopropoxyimino)ethyl)pyridin-2(1H)-one (0.2 g) in methanol ( 2 ml) was dissolved in tetrahydrofuran (2 ml), sodium borohydride (20 mg) was added under ice-cooling, and the mixture was stirred for 30 minutes. A saturated aqueous ammonium chloride solution was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.15 g of the desired compound. Yield 75%.
1 H-NMR (CDCl 3 ) δ: 7.52-2.73 (10H, m), 3.81 (3H, s), 2.22 (3H, s), 1.27(6H, m)
（工程５）
N-((2S)-1-(5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-((E)-1-(isopropoxyimino)ethyl)-2-oxopyridin-1(2H)-yl)propan-2-yl)isobutyramideの合成
Figure JPOXMLDOC01-appb-C000013
 (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-(1isopropoxyimino)ethyl)pyridin-2(1H)-one（０．３３ｇ）をＮ，Ｎ－ジメチルホルムアミド（４ｍｌ）に溶解させ、炭酸セシウム（０．４０ｇ）、(S)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate（０．４５ｇ）を加え、70°Cにて４時間撹拌した。反応液に水を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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：ヘキサン／酢酸エチル）で精製し、得られたもの１，４－ジオキサン（２ｍｌ）に溶解させ、４規定塩化水素/１，４－ジオキサン溶液（２ｍｌ）を加え、室温にて４時間撹拌した。反応液を濃縮し、得られた残渣を塩化メチレン（４ｍｌ）に溶解させ、氷冷下、トリエチルアミン（０．２ｍｌ）、isobutanoyl chloride（０．０４ｍｌ）を加え３０分撹拌した。反応液を減圧濃縮し、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：クロロホルム／酢酸エチル）で精製し、目的化合物（upper） ０．０３５ｇと (lower) ０．０３５ｇを得た。収率はそれぞれ８％得られた目的物の1H-NMRを以下に示す。
(upper) 1H-NMR (CDCl3). 7.43-2.11 (15H, m), 3.84 (3H, s), 2.14 (3H, s),1.28-0.92(15H, m).(lower) 1H-NMR (CDCl3) δ: 7.20-2.19 (15H, m), 3.84 (3H, s), 2.13 (3H, s),1.28-0.92(15H, m). (Step 5)
N-((2S)-1-(5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-((E)-1-(isopropoxyimino)ethyl)-2-oxopyridin-1 Synthesis of (2H)-yl)propan-2-yl)isobutyramide
Figure JPOXMLDOC01-appb-C000013
 (E)-5-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-(1isopropoxyimino)ethyl)pyridin-2(1H)-one (0.33 g) was added to N,N-dimethyl It was dissolved in formamide (4 ml), cesium carbonate (0.40 g) and (S)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonate (0.45 g) were added, and the mixture was stirred at 70°C for 4 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate). ,4-dioxane solution (2 ml) was added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated, the resulting residue was dissolved in methylene chloride (4 ml), triethylamine (0.2 ml) and isobutanoyl chloride (0.04 ml) were added under ice-cooling, and the mixture was stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: chloroform/ethyl acetate) to obtain 0.035 g of the target compound (upper) and 0.035 g (lower). The 1 H-NMR of the desired product obtained with a yield of 8% is shown below.
(upper) 1 H-NMR (CDCl 3 ). 7.43-2.11 (15H, m), 3.84 (3H, s), 2.14 (3H, s), 1.28-0.92(15H, m).(lower) 1 H- NMR (CDCl 3 ) δ: 7.20-2.19 (15H, m), 3.84 (3H, s), 2.13 (3H, s), 1.28-0.92(15H, m).
〔実施例３〕
Methyl2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((isopropoxyimino)methyl)-4-oxo-1,4-dihydropyridin-3-yl)benzoateの合成
（工程１）
1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oximeの合成
Figure JPOXMLDOC01-appb-C000014
 4-methoxynicotinaldehyde（３．０ｇ）をエタノール（３０ｍｌ）、クロロホルム（３０ｍｌ）に溶解させ、ピリジン（２．０ｇ）、2-(aminooxy)propane hydrochloride(２．８０ｇ)を加え、室温にて１時間攪拌した。
　溶媒を減圧留去し、飽和炭酸水素ナトリウム水溶液を加え、クロロホルムで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し得られた残渣をＮ，Ｎ－ジメチルホルムアミド（５０ｍｌ）に溶解させ、ｐ－トルエンスルホン酸一水和物（１０．５ｇ）、塩化リチウム（２．３０ｇ）を加え、80°Cにて６時間撹拌した。
　反応液に飽和炭酸水素ナトリウム水溶液を加え、クロロホルムで抽出、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し得られた残渣をＮ，Ｎ－ジメチルホルムアミド（５０ｍｌ）に溶解させ、氷冷下、炭酸カリウム（３．０ｇ）、２－ブロモ－５’－フルオロ－２’－メトキシアセトフェノン（５．５０ｇ）を加え、室温にて３時間撹拌した。
　反応液に水を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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：クロロホルム／メタノール）で精製し、目的化合物６．５０ｇを得た。収率８５％。
　得られた目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 8.74-6.43(7H, m), 5.18 (1.6H, s), 5.12(0.4H, s), 4.44-4.30(1H, m), 4.01(3H, s), 1.28-1.23(6H, m). [Example 3]
Synthesis of Methyl2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((isopropoxyimino)methyl)-4-oxo-1,4-dihydropyridin-3-yl)benzoate ( process 1)
Synthesis of 1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime
Figure JPOXMLDOC01-appb-C000014
 Dissolve 4-methoxynicotinaldehyde (3.0 g) in ethanol (30 ml) and chloroform (30 ml), add pyridine (2.0 g) and 2-(aminooxy)propane hydrochloride (2.80 g), and stir at room temperature for 1 hour. did.
The solvent was distilled off under reduced pressure, a saturated aqueous sodium hydrogencarbonate solution was added, the extract was extracted with chloroform, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was dissolved in N,N-dimethylformamide (50 ml). Stir at °C for 6 hours.
A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, extracted with chloroform, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was dissolved in N,N-dimethylformamide (50 ml) and treated with potassium carbonate (3.0 g) and 2-bromo-5'-fluoro-2'-methoxyacetophenone under ice-cooling. (5.50 g) was added and stirred at room temperature for 3 hours.
Water was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: chloroform/methanol) to obtain 6.50 g of the desired compound. Yield 85%.
1 H-NMR of the obtained desired product is shown below.
1 H-NMR (CDCl 3 ) δ: 8.74-6.43(7H, m), 5.18 (1.6H, s), 5.12(0.4H, s), 4.44-4.30(1H, m), 4.01(3H, s) , 1.28-1.23(6H, m).
（工程２）
5-bromo-1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oximeの合成
Figure JPOXMLDOC01-appb-C000015
 1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime(６．５０ｇ）をメタノール（３０ｍｌ）、テトラヒドロフラン（３０ｍｌ）に溶解させ、氷冷下、水素化ホウ素ナトリウム（６００ｍｇ）を加え１０分撹拌した。
　反応液に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し得られた残渣を塩化メチレン（８０ｍｌ）に溶解させ、Ｎ－ブロモスクシンイミド（３．３０ｇ）を加え、室温にて４時間撹拌した。
　反応液に水を加え、酢酸エチルで抽出、水、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧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：ヘキサン／酢酸エチル）で精製し、目的化合物６．９０ｇを得た。収率８７％。
　得られた目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 9.02-6.82 (6H, m), 5.86-3.48(5H, m), 3.91 (2.3H, s), 3.89 (0.7H, s), 1.40-1.28(6H, m). (Step 2)
Synthesis of 5-bromo-1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime
Figure JPOXMLDOC01-appb-C000015
 1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime (6.50 g) was dissolved in methanol (30 ml), tetrahydrofuran ( 30 ml), sodium borohydride (600 mg) was added under ice-cooling, and the mixture was stirred for 10 minutes.
A saturated aqueous ammonium chloride solution was added to the reaction solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was dissolved in methylene chloride (80 ml), N-bromosuccinimide (3.30 g) was added, and the mixture was stirred at room temperature for 4 hours.
Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 6.90 g of the desired compound. Yield 87%.
1 H-NMR of the obtained desired product is shown below.
1 H-NMR (CDCl 3 ) δ: 9.02-6.82 (6H, m), 5.86-3.48(5H, m), 3.91 (2.3H, s), 3.89 (0.7H, s), 1.40-1.28(6H, m).
（工程３）
methyl2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((isopropoxyimino)methyl)-4-oxo-1,4-dihydropyridin-3-yl)benzoateの合成
Figure JPOXMLDOC01-appb-C000016
 5-bromo-1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime（１．０ｇ）を１，４－ジオキサン（２５ｍｌ）、水（３ｍｌ）に溶解させ、ジクロロビス[ジーｔ－ブチル（４－ジメチルアミノフェニル）]ホスフィン]パラジルム（ＩＩ）（０．２０ｇ）、炭酸カリウム（０．７０ｇ）、２－（メトキシカルボニル）フェニルボロン酸（０．７０ｇ）を加え、５時間加熱還流した。
　溶媒を減圧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：ヘキサン／酢酸エチル）で精製し、目的化合物０．５０ｇを得た。収率４４％。
　得られた目的物の1H-NMRを以下に示す。
1H-NMR (CDCl3) δ: 8.93-6.80 (10H, m), 5.23-3.10(11H, m), 1.34-1.24(6H, m). (Step 3)
Synthesis of methyl2-(1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-5-((isopropoxyimino)methyl)-4-oxo-1,4-dihydropyridin-3-yl)benzoate
Figure JPOXMLDOC01-appb-C000016
 5-bromo-1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-4-oxo-1,4-dihydropyridine-3-carbaldehyde O-isopropyl oxime (1.0 g) - dioxane (25 ml), dissolved in water (3 ml), dichlorobis[di-t-butyl(4-dimethylaminophenyl)]phosphine]paradylum (II) (0.20 g), potassium carbonate (0.70 g), 2- (Methoxycarbonyl)phenylboronic acid (0.70 g) was added, and the mixture was heated under reflux for 5 hours.
The residue obtained by distilling off the solvent under reduced pressure was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 0.50 g of the desired compound. Yield 44%.
1 H-NMR of the obtained desired product is shown below.
1 H-NMR (CDCl 3 ) δ: 8.93-6.80 (10H, m), 5.23-3.10(11H, m), 1.34-1.24(6H, m).
　前記の実施例と同様の方法で製造した含窒素ヘテロアリール化合物の一部を表１および表２に示す。表中には、各化合物の物性として融点（℃）または物性を併せて示す。 Tables 1 and 2 show some of the nitrogen-containing heteroaryl compounds produced in the same manner as in the above Examples. The table also shows the melting point (°C) or physical properties of each compound as physical properties.
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-I000018
Figure JPOXMLDOC01-appb-I000019
Figure JPOXMLDOC01-appb-I000020
Figure JPOXMLDOC01-appb-I000021
Figure JPOXMLDOC01-appb-I000022
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-I000018
Figure JPOXMLDOC01-appb-I000019
Figure JPOXMLDOC01-appb-I000020
Figure JPOXMLDOC01-appb-I000021
Figure JPOXMLDOC01-appb-I000022
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-I000024
Figure JPOXMLDOC01-appb-I000025
Figure JPOXMLDOC01-appb-I000026
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-I000024
Figure JPOXMLDOC01-appb-I000025
Figure JPOXMLDOC01-appb-I000026
　表中の化合物の一部については、その１Ｈ－ＮＭＲデータを表３に示す。
Figure JPOXMLDOC01-appb-T000027
 Table 3 shows the 1 H-NMR data of some of the compounds in the table.
Figure JPOXMLDOC01-appb-T000027
　表中の化合物の一部については、液体クロマトグラフィー質量分析法(ＬＣＭＳ)における保持時間を表４及び表５に示す。
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
 Tables 4 and 5 show retention times in liquid chromatography-mass spectrometry (LCMS) for some of the compounds in the table.
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
　分析条件は以下に示す。
　Ｗａｔｅｒｓ ＣＯＲＴＥＣＳ ＵＰＬＣ Ｃ１８カラム（ウォーターズ社製、２．１×５０mm、１．６μm）を、温度４０℃および流量０．６mL/分、２μL注入、移動相(Ａ)０．１%ギ酸を含む水、移動相(Ｂ)アセトニトリルで使用し、保持時間を分単位（分間）で表した。　 (I)泳動はＡＣＱＵＩＴＹ ＵＰＬＣ Ｈ-Ｃｌａｓｓ（ウォーターズ社製）にてＡＣＱＵＩＴＹ ＵＰＬＣフォトダイオードアレイ（ＰＤＡ）eλ検出器（ウォーターズ社製）及びＡＣＱＵＩＴＹ ＱＤａ 検出器(正及び負イオンエレクトロスプレーモードで、ＵＶ ＰＤＡ検出、ウォーターズ社製)で行い、移動相(Ｂ)の濃度を、１．５分の直線勾配で３０質量％から９５質量%に上げ、(II)０．５分間９５質量%で維持し、(III)直ちに３０質量%(Ｂ)に下げ、(IV)０．５０分間３０質量%で維持した。 Analysis conditions are shown below.
Waters CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 µm), temperature 40°C and flow rate 0.6 mL/min, 2 µL injection, mobile phase (A) water containing 0.1% formic acid, Mobile phase (B) was used with acetonitrile and retention times are expressed in minutes (minutes). (I) Electrophoresis was performed with ACQUITY UPLC H-Class (Waters) using an ACQUITY UPLC photodiode array (PDA) eλ detector (Waters) and an ACQUITY QDa detector (in positive and negative ion electrospray mode, UV PDA). Detection, manufactured by Waters), the concentration of the mobile phase (B) is increased from 30% by mass to 95% by mass with a linear gradient of 1.5 minutes, and (II) is maintained at 95% by mass for 0.5 minutes, (III) Immediately lowered to 30% by weight (B) and (IV) maintained at 30% by weight for 0.50 minutes.
　さらに、含窒素ヘテロアリール化合物の一部を表６に示す。表中には、各化合物の物性として融点（℃）または物性を併せて示す。いくつかの化合物については、異性体混合物であることも示した。 Furthermore, Table 6 shows some of the nitrogen-containing heteroaryl compounds. The table also shows the melting point (°C) or physical properties of each compound as physical properties. Some compounds were also shown to be isomeric mixtures.
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-I000031
Figure JPOXMLDOC01-appb-I000032
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-I000031
Figure JPOXMLDOC01-appb-I000032
　表中の化合物の一部については、液体クロマトグラフィー質量分析法(ＬＣＭＳ)における保持時間を示す。
　液体クロマトグラフィー質量分析法(ＬＣＭＳ)の分析条件は以下に示す。
　Ｗａｔｅｒｓ ＣＯＲＴＥＣＳ ＵＰＬＣ Ｃ１８カラム（ウォーターズ社製、２．１×５０mm、１．６μm）を、温度４０℃および流量０．６mL/分、２μL注入、移動相(Ａ)０．１%ギ酸を含む水、移動相(Ｂ)アセトニトリルで使用し、保持時間を分単位（分間）で表した。
　(I)泳動はＡＣＱＵＩＴＹ ＵＰＬＣ Ｈ-Ｃｌａｓｓ（ウォーターズ社製）にてＡＣＱＵＩＴＹ ＵＰＬＣフォトダイオードアレイ（ＰＤＡ）eλ検出器（ウォーターズ社製）及びＡＣＱＵＩＴＹ ＱＤａ 検出器(正及び負イオンエレクトロスプレーモードで、ＵＶ ＰＤＡ検出、ウォーターズ社製)で行い、以下に示すMethod (A)またはMethod (B)の方法を用いた。
Method (A)：
移動相(Ｂ)の濃度を３０質量％で０．１５分維持し、その後１．３５分の直線勾配で３０質量％から９５質量%に上げ、(II)０．５分間９５質量%で維持し、(III)直ちに３０質量%(Ｂ)に下げ、(IV)０．５０分間３０質量%で維持した。
Method (B): 
移動相(Ｂ)の濃度を３０質量％で０．１５分維持し、その後0．8５分の直線勾配で３０質量％から９５質量%に上げ、(II)１.０分間９５質量%で維持し、(III)直ちに３０質量%(Ｂ)に下げ、(IV)０．５０分間３０質量%で維持した。 Retention times in liquid chromatography mass spectrometry (LCMS) are given for some of the compounds in the table.
Analysis conditions for liquid chromatography mass spectrometry (LCMS) are shown below.
Waters CORTECS UPLC C18 column (manufactured by Waters, 2.1 x 50 mm, 1.6 µm), temperature 40°C and flow rate 0.6 mL/min, 2 µL injection, mobile phase (A) water containing 0.1% formic acid, Mobile phase (B) was used with acetonitrile and retention times are expressed in minutes (minutes).
(I) Electrophoresis was performed on ACQUITY UPLC H-Class (Waters) using an ACQUITY UPLC photodiode array (PDA) eλ detector (Waters) and an ACQUITY QDa detector (in positive and negative ion electrospray mode, UV PDA). Detection, manufactured by Waters Co., Ltd.), and Method (A) or Method (B) shown below was used.
Method (A):
The concentration of the mobile phase (B) was maintained at 30 wt% for 0.15 min, then increased linearly from 30 wt% to 95 wt% for 1.35 min, and (II) maintained at 95 wt% for 0.5 min. (III) immediately lowered to 30% by weight (B) and (IV) maintained at 30% by weight for 0.50 minutes.
Method (B):
The concentration of the mobile phase (B) was maintained at 30 wt% for 0.15 min, then increased linearly from 30 wt% to 95 wt% in 0.85 min, and (II) maintained at 95 wt% for 1.0 min. (III) immediately lowered to 30% by weight (B) and (IV) maintained at 30% by weight for 0.50 minutes.
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
　〔生物試験〕
　本発明の含窒素ヘテロアリール化合物が、農園芸用殺菌剤の有効成分として有用であることを以下の試験例で示す。
（試験用乳剤の調製）
　本発明の含窒素ヘテロアリール化合物５重量部、Ｎ，Ｎ－ジメチルホルムアミド９３．５重量部、およびポリオキシエチレンソルビタンモノラウレート（ＴＷＥＥＮ（登録商標）２０）１．５重量部を混合し、溶解させて、有効成分５％の乳剤(Ｉ)を得た。 [Biological test]
The following test examples demonstrate that the nitrogen-containing heteroaryl compound of the present invention is useful as an active ingredient of agricultural and horticultural fungicides.
(Preparation of test emulsion)
5 parts by weight of the nitrogen-containing heteroaryl compound of the present invention, 93.5 parts by weight of N,N-dimethylformamide, and 1.5 parts by weight of polyoxyethylene sorbitan monolaurate (TWEEN (registered trademark) 20) were mixed and dissolved. to give an emulsion (I) containing 5% active ingredient.
　防除価は、下記の式により計算した。 The control value was calculated using the following formula.
　［数１］
防除価（％）＝１００－{処理区における病斑面積率／無処理区における病斑面積率}×１００ [Number 1]
Control value (%) = 100-{lesion area ratio in treated area / lesion area ratio in untreated area} × 100
（試験例１）リンゴ黒星病防除試験
　乳剤（Ｉ）に含窒素ヘテロアリール化合物の濃度が１２５ｐｐｍになるように水を加え、溶解させて薬剤溶液を得た。続いて育苗用ポットで栽培したリンゴ幼苗（品種「王林」、３～４葉期）に、前記薬剤溶液を散布した。風乾後、リンゴ黒星病菌（Venturia inaequalis）の分生胞子を接種した（処理区）。対照として、薬剤溶液を散布しなかったリンゴ幼苗に同様に接種した（無処理区）。それらを、明暗を１２時間毎に繰り返す２０℃の湿室に静置した。
　接種から２週間経過した日にリンゴ幼苗の葉を目視観察して、病斑面積率を求め、防除価を算出した。 (Test Example 1) Apple scab control test Water was added to the emulsion (I) so that the concentration of the nitrogen-containing heteroaryl compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on apple seedlings (variety “Orin”, 3-4 leaf stage) cultivated in pots for raising seedlings. After air-drying, conidia of Venturia inaequalis were inoculated (treated area). As a control, apple seedlings not sprayed with the drug solution were similarly inoculated (untreated group). They were placed in a moist chamber at 20°C with alternating light and dark cycles every 12 hours.
Two weeks after the inoculation, the leaves of the young apple seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.
　Ａ-７、Ａ-８、Ａ-９、Ａ-１１、Ａ-１６、Ａ-２２、Ａ-２３、Ａ－２８、Ａ－３１、Ａ－３２、Ａ－３３、Ａ－３４、ａ－３、ａ－４、及びａ－１１の化合物ついて、リンゴ黒星病防除試験を行った。いずれの化合物も７５％以上の防除価を示した。 A-7, A-8, A-9, A-11, A-16, A-22, A-23, A-28, A-31, A-32, A-33, A-34, a- 3, a-4, and a-11 were subjected to an apple scab control test. All compounds showed a control value of 75% or more.
（試験例）Ｆｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍに対する抗菌試験
　グルコースを添加したＭｉｎｉｍａｌ　ＳＤ　Ｂａｓｅ培地にＦｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍの胞子を添加して分散させ、さらにジメチルスルホキシドに溶解した含窒素ヘテロアリール化合物を２５ｐｐｍとなるように添加混合し、これらを９６穴マイクロプレート上に分注し、暗所、２５℃で３～４日間培養した。培養後、マイクロプレートリーダーで波長４０５ｎｍにおける濁度を測定し、無処理の場合と比較してＦｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍの生育阻害率（％）を求めた。
その結果、下記の化合物が５０％以上の優れた生育阻害率を示した。
化合物番号：Ａ－２、Ａ－１１、Ａ－２２、Ａ－２３、Ａ－２８、Ａ－２９、Ａ－３０、Ａ－３１、Ａ－３２、Ａ－３３、Ａ－３４、Ａ－３５、Ａ－３６、Ａ－３７。
  (Test example) Antibacterial test against Fusarium graminearum Spores of Fusarium graminearum were added to Minimal SD Base medium containing glucose and dispersed, and then a nitrogen-containing heteroaryl compound dissolved in dimethyl sulfoxide was added and mixed to a concentration of 25 ppm, These were dispensed onto 96-well microplates and incubated in the dark at 25°C for 3-4 days. After culturing, the turbidity at a wavelength of 405 nm was measured using a microplate reader, and the growth inhibition rate (%) of Fusarium graminearum was determined in comparison with the untreated case.
As a result, the following compounds showed an excellent growth inhibition rate of 50% or more.
Compound numbers: A-2, A-11, A-22, A-23, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35 , A-36, A-37.

Claims (6)

  1. 　式（Ｉ－１）で表される化合物、式（Ｉ－２）で表される化合物、若しくは式（Ｉ－３）で表される化合物またはそれらの塩。
    Figure JPOXMLDOC01-appb-C000001
     〔式（Ｉ－１）、式（Ｉ－２）、および式（Ｉ－３）中、
    　Ｙ１は、酸素原子または硫黄原子を示し；
    　Ｘ１、Ｘ２、およびＸ４は、それぞれ独立に、水素原子、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基、またはＲ１Ｏ－Ｎ＝ＣＲ６－で表される基を示し；
    　Ｒ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
    　Ｒ２は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
    　Ｒ３は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
    　Ｒ４は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示し、
    　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよく、
    　Ｒ５は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、または置換若しくは無置換のＣ６～１０アリール基を示し、
    　Ｒ６は、水素原子、ハロゲノ基、アミノ基、置換若しくは無置換のモノＣ１～６アルキルアミノ基、置換若しくは無置換のジＣ１～６アルキルアミノ基、置換若しくは無置換のＣ１～６アルキル基、置換もしくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、または置換若しくは無置換の５～６員環のヘテロシクリル基を示し；
    　Ｘ３は、水素原子、ハロゲノ基、置換若しくは無置換の直鎖Ｃ１～６アルキル基、置換若しくは無置換の直鎖Ｃ２～６アルケニル基、置換若しくは無置換の直鎖Ｃ２～６アルキニル基、Ｒ１－ＣＯ－で表される基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換の４～６員環のヘテロシクリル基、ＲＮ１Ｏ－で表される基、ＲＮ１－ＣＯ－Ｏ－で表される基、ＲＮ１－Ｏ－ＣＯ－Ｏ－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－Ｏ－で表される基、ＲＮ１－ＣＳ－Ｏ－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＳ－Ｏ－で表される基、ＲＮ１ＲＮ２Ｎ－で表される基、ＲＮ１－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－ＣＯ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－Ｏ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＯ－ＣＯ－ＮＲＮ２－で表される基、ＲＮ１－ＣＳ－ＮＲＮ２－で表される基、ＲＮ１ＲＮ１Ｎ－ＣＳ－ＮＲＮ２－で表される基、ＲＮ１ＳＯ２－ＮＲＮ２－で表される基、またはＲＮ１－Ｃ（＝ＮＲＮ１）－ＮＲＮ２－で表される基を示し、
    　ＲＮ１、およびＲＮ２は、それぞれ独立に、水素原子、置換若しくは無置換の直鎖Ｃ１～６アルキル基、置換若しくは無置換の直鎖Ｃ２～６アルケニル基、置換若しくは無置換の直鎖Ｃ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の４～６員環のヘテロシクリル基を示し、ここで、ＲＮ１とＲＮ１、またはＲＮ１とＲＮ２は、一緒になって二価の有機基を形成してもよく；
    　Ｂは、単結合、酸素原子、硫黄原子、スルフィニル基、スルホニル基、または－ＮＲＮ３－表される基を示し、ＲＮ３は、水素原子、置換若しくは無置換のＣ１～６アルキル基、ホルミル基、または置換若しくは無置換のＣ１～６アルキルカルボニル基を示し；
    　Ａは、置換若しくは無置換のＣ１～６アルキレン基、置換若しくは無置換のＣ２～６アルケニレン基、置換若しくは無置換のＣ２～６アルキニレン基、または置換若しくは無置換のＣ３～６シクロアルキレン基を示し；
    　Ｑは、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～１０員環のヘテロシクリル基を示す。〕     A compound represented by formula (I-1), a compound represented by formula (I-2), a compound represented by formula (I-3), or a salt thereof.
    Figure JPOXMLDOC01-appb-C000001
     [In formula (I-1), formula (I-2), and formula (I-3),
    Y 1 represents an oxygen atom or a sulfur atom;
    X 1 , X 2 and X 4 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2- 6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group , substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 5- to 6-membered heterocyclyl group, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group, nitro group, cyano group, R 1 —CO— a carboxy group, a group represented by R 2 —O—CO—, a group represented by R 3 R 4 N—, a group represented by R 3 R 4 N—CO—, R 1 — a group represented by CO—O—, a group represented by R 1 —CO—NR 5 —, a group represented by R 2 —O—CO—O—, and R 2 —O—CO—NR 5 — A group represented by R 3 R 4 N—CO—O— A group represented by R 3 R 4 N—CO—NR 5 — R 2 SO 2 —NR 5 — a group represented by R 3 R 4 N--SO 2 -- or a group represented by R 1 ON=CR 6 --;
    R 1 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
    R 2 is each independently a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3-6 cyclo an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group,
    R 3 is each independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3 ~6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 5- to 6-membered heterocyclyl group,
    each R 4 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
    wherein R 3 and R 4 may together form a divalent organic group,
    each R 5 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group;
    R 6 is a hydrogen atom, a halogeno group, an amino group, a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted di-C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, or a substituted or unsubstituted 5- to 6-membered heterocyclyl group;
    X 3 is a hydrogen atom, a halogeno group, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2-6 alkynyl group, R a group represented by 1 -CO-, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 4- to 6-membered heterocyclyl group, R N1 O A group represented by -, a group represented by R N1 --CO--O--, a group represented by R N1 --O--CO--O--, a group represented by R N1 R N1 N--CO--O-- , a group represented by R N1 -CS-O-, a group represented by R N1 R N1 N-CS-O-, a group represented by R N1 R N2 N-, R N1 -CO-NR N2 - A group represented by R N1 —CO—CO—NR N2 — A group represented by R N1 —O—CO—NR N2 — R N1 R N1 N—CO—NR N2 — A group represented by R N1 R N1 N—CO—CO—NR N2 — A group represented by R N1 —CS-NR N2 — R N1 R N1 N—CS-NR N2 — a group represented by R N1 SO 2 —NR N2 — or a group represented by R N1 —C(=NR N1 )—NR N2 —,
    R N1 and R N2 are each independently a hydrogen atom, a substituted or unsubstituted linear C1-6 alkyl group, a substituted or unsubstituted linear C2-6 alkenyl group, a substituted or unsubstituted linear C2- 6 alkynyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C6-10 aryl group, or substituted or unsubstituted 4- to 6-membered heterocyclyl group, wherein R N1 and R N1 , or R N1 and R N2 may together form a divalent organic group;
    B is a single bond, an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR N3 -, where R N3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a formyl group , or a substituted or unsubstituted C1-6 alkylcarbonyl group;
    A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, or a substituted or unsubstituted C3-6 cycloalkylene group. ;
    Q represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered heterocyclyl group. ]
  2. 　Ｘ２が、Ｒ１Ｏ－Ｎ＝ＣＲ６－で表される基である、請求項１に記載の化合物またはそれらの塩。 The compound or a salt thereof according to claim 1, wherein X 2 is a group represented by R 1 ON=CR 6 -.
  3. 　請求項１または２に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する農園芸用殺菌剤。 An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 or 2 and salts thereof.
  4. 　種子処理用である、請求項３に記載の農園芸用殺菌剤。 The agricultural and horticultural fungicide according to claim 3, which is for seed treatment.
  5. 　請求項１または２に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する殺線虫剤。 A nematicide containing at least one selected from the group consisting of the compound according to claim 1 or 2 and salts thereof as an active ingredient.
  6. 　請求項１または２に記載の化合物、およびそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する医療用・動物用抗真菌剤。 A medical/veterinary antifungal agent containing, as an active ingredient, at least one selected from the group consisting of the compounds according to claim 1 or 2 and salts thereof.
PCT/JP2022/018006 2021-04-23 2022-04-18 Nitrogen-containing heteroaryl compound, agricultural and horticultural anti-bacterial agent, nematicide, and anti-fungal agent for medical and veterinary uses WO2022224924A1 (en)

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