WO2022224924A1 - Composé hétéroarylique contenant de l'azote, agent antibactérien agricole et horticole, nématicide et agent antifongique pour utilisations médicales et vétérinaires - Google Patents

Composé hétéroarylique contenant de l'azote, agent antibactérien agricole et horticole, nématicide et agent antifongique pour utilisations médicales et vétérinaires 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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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
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D213/78—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
    • 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
    • C07D213/89—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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D241/18—Oxygen or sulfur atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—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
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to 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

La présente invention concerne un composé hétéroarylique contenant de l'azote qui présente une excellente activité bactéricide et antibactérienne et une excellente innocuité et qui peut être synthétisé de manière industriellement avantageuse ; et un agent antibactérien agricole et horticole le contenant en tant que principe actif.　Ce composé hétéroarylique contenant de l'azote est un composé représenté par la formule (I-1), la formule (I-2) ou la formule (I-3), ou un sel de ceux-ci.　Dans la formule (I-1), la formule (I-2) et la formule (I-3) : Y1 représente un atome d'oxygène ou un atome de soufre ; X1, X2 et X4 représentent chacun indépendamment un atome d'hydrogène, un groupe halogéno, un groupe alkyle en C1-6 substitué ou non substitué, un groupe alcényle en C2-6 substitué ou non substitué, ou un groupe similaire ; X3 représente un atome d'hydrogène, un groupe alkyle en C1-6 à chaîne linéaire substitué ou non substitué, un groupe alcényle en C2-6 à chaîne linéaire substitué ou non substitué, ou un groupe similaire ; B représente une simple liaison, un atome d'oxygène ou un groupe similaire ; A représente un groupe alkylène en C1-6 substitué ou non substitué, un groupe alcénylène en C2-6 substitué ou non substitué, ou un groupe similaire ; et Q représente un groupe aryle en C6-10 substitué ou non substitué ou un groupe hétérocyclyle d'un cycle à 5 à 10 chaînons substitué ou non substitué.
PCT/JP2022/018006 2021-04-23 2022-04-18 Composé hétéroarylique contenant de l'azote, agent antibactérien agricole et horticole, nématicide et agent antifongique pour utilisations médicales et vétérinaires WO2022224924A1 (fr)

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LUCY LIN, LEWIS D. TURNER, PETER ŠILHÁR, SABINE PELLETT, ERIC A. JOHNSON AND KIM D. JANDA: "Identification of 3-hydroxy-1,2-dimethylpyridine-4(1H)-thione as a metal-binding motif for the inhibition of botulinum neurotoxin A", RSC MEDICINAL CHEMISTRY, vol. 12, no. 1, 1 January 2021 (2021-01-01), pages 137 - 143, XP009540423, DOI: 10.1039/D0MD00320D *

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