WO2023106175A1 - ウラシル化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤 - Google Patents

ウラシル化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤 Download PDF

Info

Publication number
WO2023106175A1
WO2023106175A1 PCT/JP2022/044128 JP2022044128W WO2023106175A1 WO 2023106175 A1 WO2023106175 A1 WO 2023106175A1 JP 2022044128 W JP2022044128 W JP 2022044128W WO 2023106175 A1 WO2023106175 A1 WO 2023106175A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
represented
group represented
Prior art date
Application number
PCT/JP2022/044128
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
伸哉 幸堀
貴昭 寺西
載▲ヒョン▼ 金
頼人 ▲桑▼原
達弘 川▲崎▼
睦幸 斎賀
Original Assignee
日本曹達株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日本曹達株式会社 filed Critical 日本曹達株式会社
Priority to JP2023566261A priority Critical patent/JPWO2023106175A1/ja
Publication of WO2023106175A1 publication Critical patent/WO2023106175A1/ja

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms

Definitions

  • the present invention relates to uracil compounds and agricultural and horticultural fungicides. More specifically, the present invention relates to a uracil 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. 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 claims priority to Japanese Patent Application No. 2021-199391 filed on December 8, 2021, the contents of which are incorporated herein.
  • Patent Literature 1 discloses a compound represented by the formula (A) and the like. It is disclosed that this compound has bactericidal activity, antifungal activity, and the like.
  • An object of the present invention is to provide a uracil 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.
  • 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 represents an oxygen atom or a sulfur atom
  • X 1 and X 2 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6
  • a compound represented by formula (II) or a salt thereof [In formula (II), Y represents an oxygen atom or a sulfur atom; X 1 and X 2 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group , hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C
  • the uracil compound of the present invention has excellent 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 uracil compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as 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] Y represents an oxygen atom or a sulfur atom.
  • Y is preferably an oxygen atom.
  • X 1 and X 2 are each independently a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, substituted or unsubstituted C2-6 alkynyloxy group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C
  • 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 iodine group.
  • the “C1-6 alkyl group” for X 1 and X 2 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 and X 2 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 can be mentioned.
  • the "C2-6 alkynyl group" for X 1 and X 2 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 and X 2 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, 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 and X 2 include vinyloxy, allyloxy, propenyloxy, butenyloxy and the like.
  • Examples of the “C2-6 alkynyloxy group” for X 1 and X 2 include an ethynyloxy group and a propargyloxy group.
  • Examples of the "C1-6 alkylthio group" for X 1 and X 2 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. can be done.
  • Examples of the “C1-6 alkylsulfinyl group” for X 1 and X 2 include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.
  • Examples of the “C1-6 alkylsulfonyl group” for X 1 and X 2 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”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group” or “C1-6 alkylsulfonyl group”, fluoro group, chloro group, bromo group, iodo group Halogeno groups such as; hydroxyl group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1 ⁇ 6 haloalkoxy group such as trifluoromethoxy group; 6 alkylideneamino) oxy group; cyclopropyl group, cyclobutyl group, cyclopentyl group, C3-6 cycloalkyl group such as cyclohexyl group; phenyl group, C6-10 aryl group such as naphthyl group;
  • Examples of the “C3-6 cycloalkyl group” for X 1 and X 2 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the “C3-6 cycloalkyloxy group” for X 1 and X 2 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 and X 2 include phenyl group, naphthyl group, indanyl group, indenyl group, tetralinyl group, and the like.
  • Examples of the “C6-10 aryloxy group” for X 1 and X 2 include a phenoxy group and a naphthoxy group.
  • Examples of the “C6-10 arylthio group” for X 1 and X 2 include a phenylthio group and a naphthylthio group.
  • Examples of the “C6-10 arylsulfinyl group” for X 1 and X 2 include a phenylsulfinyl group and a naphthylsulfinyl group.
  • Examples of the “C6-10 arylsulfonyl group” for X 1 and X 2 include a phenylsulfonyl group and a naphthylsulfonyl group.
  • the “5- to 6-membered heterocyclyl group” for X 1 and X 2 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 used as ring-constituting atoms. is a group containing 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 and X 2 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.
  • C3-6 cycloalkyl group "C3-6 cycloalkyloxy group”, “C6-10 aryl group”, “C6-10 aryloxy group”, “C6-10 arylthio group” in X 1 and X 2
  • a fluoro group chloro group, bromo group, halogeno group such as iodine group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, C1-6 alkyl groups such as n-pentyl group and n-hexyl group; chloromethyl group, chloroeth
  • R 1 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted Alternatively, it represents an 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.
  • 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 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; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexy
  • 6-membered 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 phenyl group, naphthyl group, indenyl group, indanyl group and tetralinyl group.
  • 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, and isoxazolinyl 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 It represents an 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.
  • 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 group
  • 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 a fluoro group, a chloro group, a bromo group, and an iodo group; 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.
  • halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group
  • R 3 R 4 N— examples include amino group, methylamino group, dimethylamino group, i-propylamino group and the like.
  • R 3 and R 4 have the same meanings as those in the above “group represented by R 3 R 4 N—” indicate.
  • 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 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 has the same meaning as in the above “group represented by R 2 —O—CO—” .
  • Specific examples of the “group represented by R 2 —O—CO—O—” include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.
  • R 2 has the same meaning as in the above "group represented by R 2 -O-CO-”. show.
  • 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 and R 4 are the same as those in the above “group represented by R 3 R 4 N—” indicates the meaning of 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 and R 4 are the same as those in the above “group represented by R 3 R 4 N—” have similar meanings.
  • 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 the above "group represented by R 2 -O -CO-”.
  • 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 and R 4 are the same as those in the above “group represented by R 3 R 4 N—” indicate meaning.
  • Specific examples of the “group represented by R 3 R 4 N—SO 2 —” include an N,N-dimethylaminosulfonyl group.
  • R 1 has the same meaning as the above "group represented by R 1 -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.
  • R 3 and R 4 are the same as those in the above "group represented by R 3 R 4 N-”. have similar meanings.
  • X 1 is preferably a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • X 3 is 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, R 1 -CO A group represented by -, 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 and X 2 .
  • 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 ring heteroaryl group such as; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered ring heteroaryl group such as triazinyl group; indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, 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 R G1 N- R G1 in the formula may be the same or different.
  • R G1 together may be a trimethylene group, a tetramethylene group, a pentamethylene group, or a dimethyleneoxy may form a dimethylene group.
  • a group represented by R G1 R G1 N—CO— R G1 in the formula may be the same or different.
  • R G1 together may be a trimethylene group, tetramethylene group, pentamethylene group, or A methyleneoxydimethylene group may be formed.); a group represented by R G1 -CO-O-; a group represented by R G1 -CO-NR G3 - (wherein R G3 is a hydrogen atom; a C1-6 alkyl group; a halogeno group, a C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, or C1-6 alkyl group substituted with one or more substituents of a 5- to 6-membered heteroaryl group; a C6-10 aryl)C1-6 alkyl group substituted with one or more substituents selected from a 6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or (5- to 6-membered 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, 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 ring heteroaryl group such as; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered ring heteroaryl group such as triazinyl group; indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, 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 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.
  • 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—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 a fluoro group, a chloro group, a bromo group, and an iodo group; 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.
  • halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo 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 .
  • Each Q independently 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 ring heteroaryl group such as; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, 6-membered ring heteroaryl group such as triazinyl group; indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, 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".
  • a 1 is 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 show.
  • Examples of the “C1-6 alkylene group” for A 1 include methylene group, dimethylene group, trimethylene group, tetramethylene group and the like.
  • Examples of the “C2-6 alkynylene group” for A 1 include an ethynylene group (-C ⁇ C-), a propynylene group (-CH 2 -C ⁇ C-, -C ⁇ C-CH 2 -), and the like. can.
  • Examples of the “C3-6 cycloalkylene group” for A 1 include 1,2-cyclopropylene group, 1,2-cyclobutanediyl group, 1,3-cyclobutanediyl group and the like.
  • preferred A 1 is a substituted or unsubstituted C1-6 alkylene group or a substituted or unsubstituted C2-6 alkenylene group.
  • 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 ).
  • this substituent is denoted by the symbol "Ga" can be expressed as ).
  • 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 unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted substituted or
  • 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, a naphthyl group, an indenyl group, an indanyl group and a tetralinyl group.
  • 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, and isoxazolinyl 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 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-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,
  • 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 a fluoro group, a chloro group, a bromo group, and an iodo group; 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.
  • halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo 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 a fluoro group, a chloro group, a bromo group, and an iodo group; 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 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.
  • [B] B represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by -NR N3 -.
  • R N3 independently represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a 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 2 is a single bond, 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 cyclo represents an alkylene group.
  • a 2 of a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, a substituted or unsubstituted C2-6 alkynylene group, and a substituted or unsubstituted C3-6 cycloalkylene group Specific examples are the same as those exemplified in A1 .
  • R A2 is 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, a substituted or unsubstituted is a C3-6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 3- to 6-membered heterocyclyl group.
  • R A2 is 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, a substituted or unsubstituted C3-
  • Specific examples of the 6-cycloalkyl group, the substituted or unsubstituted C6-10 aryl group, and the substituted or unsubstituted 3- to 6-membered heterocyclyl group are the same as those exemplified for Ga.
  • Y in formula (I) is preferably an oxygen atom;
  • X 1 is preferably a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C1-6 alkoxy group;
  • R 1 in X 2 is preferably a substituted or unsubstituted C1-6 alkyl group, R 6 in X 2 is preferably a substituted or unsubstituted C1-6 alkyl group;
  • X 3 is preferably a substituted linear C1-6 alkyl group;
  • substituent (G) on the straight-chain C1-6 alkyl group in the substituted straight-chain C1-6 alkyl group for X 3 the following substituent groups are preferred. halogeno group, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted 3- to 10-membered heterocyclyl group, cyano group, group represented by R a —CO—, carboxy group, R b —O— A group represented by CO—, a group represented by R c R d N—, a group represented by R c R d N—CO—, a group represented by R c R d N—NR d —CO— , a group represented by R a —CO—O—, a group represented by R a —CO—NR e —, a group represented by R a —CO—CO—NR e —, R a —CO—NR a group represented by e -NR e -, a group represented by
  • 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 of compound (I) is not limited.
  • compound (I) or a salt of compound (I) 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.
  • Y represents an oxygen atom or a sulfur atom
  • X 1 and X 2 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 alkylsul
  • salt of production intermediate and production method Examples of the salt of the production intermediate represented by formula (II) are the same as the salt of the compound represented by formula (I). Moreover, the production method of the production intermediate represented by formula (II) is not limited. For example, it can be obtained by a known method as described in Examples. Also, a salt of a production intermediate can be obtained from compound (II) 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 useful 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), sooty mildew (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, Anthracnose (Colletotrichum aenigma, Colletotrichum capsici, Colletotrichum fructicola, Colletotrichum jiangxiense), powdery mildew (Leveillula taurica), etc.
  • Strawberries Botrytis cinerea, powdery mildew (Sphaerotheca humuli), anthracnose (Colletotrichum acutatum, Colletotrichum fragariae) , Phytophthora cactorum, Rhizopus stolonifer, Fusarium oxysporum, Verticillium dahliae, Sclerotinia sclerotiorum, etc.
  • Gray rot Botrytis allii
  • Gray mold Botrytis cinerea, Botrytis squamosa, Peronospora destructor, Phytophthora porri, Ciborinia allii, Botrytis squamosa, dry rot (Fusarium oxysporum), red root rot (Pyrenochaeta terrestris), black rot (Sclerotium cepivorum), rust (Puccinia allii), white silk disease (Sclerotium rolfsii), etc.
  • Leek soft rot (Pectobacterium carotovorum), downy mildew Peronospora destructor, Pleospora allii, Sclerotium cepivorum, Puccinia allii, Botrytis squamosa, 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 Peronospora parasitica, Sclerotinia sclerotiorum, Alternaria brassicicola, Botrytis cinerea, Phoma lingam, Pythium rot aphanidermatum, Pythium ultimum), white rust (Albugo macrospora), etc.
  • Lettuce rot (Pseudomonas cichorii, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), downy mildew (Bremia lactucae), gray mold (Botrytis cinerea), fungi Sclerotinia sclerotiorum, Mirafiori lettuce big-vein ophiovirus, Fusarium oxysporum, Rhizoctonia solani, Golovinomyces orontii, etc.
  • Green beans Sclerotinia sclerotiorum), Botrytis cinerea, Colletotrichum lindemuthianum, Phaeoisariopsis griseola, etc.
  • Peas Mycosphaerella blight, Botrytis cinerea, Sclerotinia sclerotiorum ), powdery mildew (Erysiphe pisi), 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, Uncinula necator, 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) , White cotton disease (unidentified pathogen), Rhizobium radiobacter, Rhizobium vitis, etc.
  • Pears Venturia nashicola, Gymnosporangium asiaticum, Alternaria kikuchiana, Ring spots (Botryosphaeria berengeriana), powdery mildew (Phyllactinia mali), blight (Phomopsis fukushii), brown spot (Stemphylium vesicarium), anthracnose (Glomerella cingulata), etc. Tea: Pestalotiopsis longiseta, P.
  • Kiwifruit Flower rot (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), canker (Pseudomonas syringae), gray mold (Botrytis cinerea), fruit soft rot (Botryosphaeria dothidea, Diaporthe sp.) ., Lasiodiplodia theobromae), soot spot (Pseudocercospora actinidiae), etc.
  • Olive Anthrax (Colletotrichum acutatum, Colletotrichum gloeosporioides), Peacock spot (Spilocaea oleaginea), etc.
  • Chestnut Anthracnose (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, Pythiumgraminicola, Xanthomonas oryzae), bacterial seedling blight (Burkholderia plantarii), brown streak (Acidovorax avenae), bacterial blight (Burkholderia glumae), leaf blight (Cercospora oryzae), rice blight (Ustilaginoidea virens), brown rice ( Alternaria alternata, Curvularia intermedia), Alternaria padwickii, Epicoccum purpurascens, etc.
  • Tobacco Sclerotinia sclerotiorum, Erysiphe cichoracearum, Phytophthora nicotianae, etc.
  • Tulip Gray Mold (Botrytis cinerea), brown spot (Botrytis tulipae), leaf rot (Rhizoctonia solani), bulb rot (Fusarium oxysporum), skin rot (Rhizoctonia solani), etc.
  • Roses scab (Diplocarpon rosae), powdery mildew Diseases (Erysiphe simulans, Podosphaera pannosa), gray mold (Botrytis cinerea), etc.
  • Chrysanthemum gray mold (Botrytis cinerea), white rust (Puccinia horiana), downy mildew (Paraperonospora minor, Peronospora danica), Pythium wilt (Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum), Rhizoctonia solani, Fusarium solani, etc.
  • Gerbera Botrytis cinerea, Podosphaera xanthii ), etc.
  • Lily leaf blight (Botrytis elliptica, Pestalotiopsis sp.), gray mold (Botrytis cinerea), etc.
  • Sunflower downy mildew (Plasmopara halstedii), sclerotinia (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea), etc.
  • Bentgrass snow rot (Sclerotinia borealis), large patch (Rhizoctonia solani), brown patch (Rhizoctonia solani), dollar spot (Sclerotinia homoeocarpa), blast (Pyricularia sp.), red scorch (Pythium aphanidermatum), Anthracnose (Colletotrichum graminicola), etc.
  • Orchard grass Powdery mildew (Erysiphe graminis), etc.
  • Soybean Purpura (Cercospora kikuchii), Downy mildew (Peronospora manshurica), Stem plague (Phytophthora sojae), Rust (Phakopsora pachyrhizi), Sclerotinia sclerotiorum, Colletotrichum truncatum, Botrytis cinerea, Elsinoe glycines, Diaporthe phaseolorum var. sojae, Damping off (Pythium spp., Fusarium) spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), etc.
  • Ginger rhizome rot (Pythium ultimum, Pythium myriotylum), white star disease (Phyllosticta zingiberis), etc.
  • Banana Panama disease (Fusarium oxysporum), sigatoka disease (Mycosphaerella fijiensis, M Mango: Colletotrichum aenigma, Xanthomonas campestris, Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp., Botrytis cinerea Rapeseed: Sclerotinia sclerotiorum, Phoma lingam, Alternaria brassicae, Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae, Peronospora parasitica, etc.
  • Coffee Hemileia vastatrix, Colletotrichum coffeanum, Cercospora coffeicola, etc.
  • Sugar cane Puccinia melanocephala, etc.
  • Maize Gloeocercospora sorghi, Puccinia sorghi, Southern Puccinia polysora, Ustilago maydis, Cochliobolus heterostrophus, Setosphaeria turcica, Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight ( Pythium spp., Fusarium spp., Rhizoctonia spp.), etc.
  • Cotton seedling wilt (Pythium sp.), rust (Phakopsora gossypii), white mold (Mycosphaerella areola), anthracnose (Glomerella gossypii), etc.
  • Hops downy mildew disease (Pseudoperonospora humuli), powdery mildew (Oidium sp., Podosphaera macularis), gray mold (Botrytis cinerea), etc.
  • the uracil 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. Specific examples of various plant parasitic nematodes that can be controlled by the nematicide of the present invention are shown below.
  • Tylenchida (a) Anguinidae, for example, Anguina spp., Anguina funesta, Anguina tritici; Ditylenchus spp., Imogusare nematode ( Ditylenchus destructor), Ditylenchus dipsaci, Ditylenchus myceliophagus; (b) Aphelenchoides family (Aphelenchoididae), for example, Aphelenchoides spp., Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi; Bursa Bursaphelenchus xylophilus, of the genus Bursaphelenchus spp.; (c) Belonolaimidae, e.g., Belonolaimus spp., Belonolaimus longicaudatus; Tylenchorhynchus s
  • 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 Species, Platylenchus brachyurus, Pratylenchus coffeae, Pinnematode (Pratylenchus curvitatus) , Pratylenchus fallax, Pratylenchus goodeyi, Pratylenchus neglectus, Pratylenchus penetrans, Platylenchus scribneri, Walnut Pratylenchus vulnus, Pratylenchus zeae; others, Nacobbus aberrans, Radopholus similis, Tylenchulus semipenetrans, 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, 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 uracil 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, ethylimole; (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 salts), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; mannkappa, 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; 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 77B strain (Trichoderma atroviride strain 77B); Trichoderma asperellum strain T34, Trichoderma asperellum strain kd; Trichoderma harzianum T-22 strain (Trichoderma harzianum strain T-22); Trichoderma virens strain G-41; Gliocladium catenulatum J1446 strain (Gliocladium catenulatum strain J1446); Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON/M/91-08; Talaromyces flavus strain SAY-Y-94-01 (Talaromyces
  • Acetylcholinesterase (AChE) inhibitor (carbamate): alanicarb, aldicarb, bendiocarb, benfuracarb, butocaboxim, butoxycarboxim, carbaryl, carbofuran, carbosulphan, ethiophenecarb, phenocarb, formethanate, furatiocarb, isoprocarb, methiocarb, methomil, 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) 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 contains, in addition to the uracil compound of the present invention, other active ingredients and agricultural and horticulturally acceptable auxiliary ingredients for formulation (e.g., 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 uracil compound of the present invention can be used as a prophylactic or therapeutic agent for controlling harmful pathogens that infect humans or animals, especially fungi.
  • 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 ( means ra 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.
  • specific examples are not limited to these.
  • the genus Absidia such as absidia corymbifera; the genus Acremonium; the genus Alternaria, such as Alternaria alternata; the genus Aspergillus, such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, Aspergillus parasiticus, and Aspergillus terreus
  • Genus Blumeria such as Blumeria graminis
  • Genus Candida such as Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, Candida tropicalis
  • Genus Cladosporium such as Cladosporium cladosporoides and Cladosporium herbarium; richium trifolii, etc.
  • Cryptococcus genera such as Cryptococcus neoformans; Curvularia genera such as Curvularia lunata; Encephalitozoon genera such as Encephalitozoon cuniculi; Epicoccum genera such as Epicoccum nigrum; Genus lum; Fusarium Fusarium genera, such as graminarium, Fusarium solani, and Fusarium sporotrichoides; Fonsecaea genera, such as Fonsecaea monophora; Histoplasma genera, such as Histoplasma capsulatum; Leptosphaeria genera, such as Leptosphaeria nodorum; Malassezia genera, such as Malassezia globosa; icola etc.
  • Penicillium such as Penicillium chrysogenum
  • Phytophthora such as Phytophthora capsici and Phytophthora infestans
  • Plasmopara such as Plasmopara viticola
  • Mocystis genus Pyricularia oryzae, etc.
  • the antifungal agent of the present invention is suitable for Aspergillus, Trichophyton or Candida, and particularly suitable for Aspergillus fumigatus or Trichophyton tonsurans.
  • 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.; semisolid 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 or vagina; ; oral administration such as ingestion through the mouth; 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, for adults, in the case of oral or parenteral (injection, infusion, etc.) administration, 0.1 to 100 mg/kg-body weight can be administered 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 uracil compounds.
  • Table 1 shows some of the uracil compounds of the present invention 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 2 shows some of the production intermediates of the uracil compound of the present invention produced in the same manner as in the above Examples. The table also shows the physical properties of each compound.
  • 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), using the method shown below.
  • the concentration of the mobile phase (B) was maintained at 30% by weight for 0.15 minutes, then increased linearly from 30% by weight to 95% by weight for 1.35 minutes, and (II) maintained at 95% by weight for 0.5 minutes.
  • (III) immediately lowered to 30% by weight (B) and (IV) maintained at 30% by weight for 0.50 minutes.
  • test emulsion 5 parts by weight of the uracil 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) are mixed and dissolved, An emulsion (I) with 5% active ingredient was obtained.
  • 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
  • Test Example 2 Wheat powdery mildew control test Water was added to the emulsion (I) so that the concentration of the uracil compound was 125 ppm, and dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on wheat seedlings (variety “Chihoku”, 1-2 leaf stage) cultivated in nursery pots. After air-drying, conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were sprinkled and inoculated (treated area). As a control, wheat seedlings not sprayed with the drug solution were inoculated in the same manner as above (untreated group). They were placed in a greenhouse at 20°C.
  • Antibacterial test against Fusarium graminearum Spores of Fusarium graminearum were added to Minimal SD Base medium to which glucose was added and dispersed. The cells were dispensed onto well microplates and incubated in the dark at 25°C for 3 days. After culturing, the turbidity at a wavelength of 405 nm was measured using a microplate reader, and the growth inhibition rate (%) of Fusarium graminearum was determined in comparison with the untreated case. As a result, the following compounds showed an excellent growth inhibition rate of 50% or more. Compound numbers: A-2, A-3, A-8.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Agronomy & Crop Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Dentistry (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
PCT/JP2022/044128 2021-12-08 2022-11-30 ウラシル化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤 WO2023106175A1 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2023566261A JPWO2023106175A1 (enrdf_load_stackoverflow) 2021-12-08 2022-11-30

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021-199391 2021-12-08
JP2021199391 2021-12-08

Publications (1)

Publication Number Publication Date
WO2023106175A1 true WO2023106175A1 (ja) 2023-06-15

Family

ID=86730278

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2022/044128 WO2023106175A1 (ja) 2021-12-08 2022-11-30 ウラシル化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤

Country Status (2)

Country Link
JP (1) JPWO2023106175A1 (enrdf_load_stackoverflow)
WO (1) WO2023106175A1 (enrdf_load_stackoverflow)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0474170A (ja) * 1990-07-13 1992-03-09 Yamasa Shoyu Co Ltd １―アミノウラシル誘導体
JPH09502178A (ja) * 1993-09-02 1997-03-04 ビーエーエスエフ アクチェンゲゼルシャフト 除草効果を持つ置換１−アミノ−３−フェニルウラシル
JPH11509531A (ja) * 1995-06-29 1999-08-24 ビーエーエスエフ アクチェンゲゼルシャフト 新規な１−アミノ−３−ベンジルウラシル
JP2012053193A (ja) * 2010-08-31 2012-03-15 Nissan Chem Ind Ltd 光配向性の新規な液晶配向剤、及び新規なジアミン化合物
JP2014533281A (ja) * 2011-11-11 2014-12-11 ニンバス アポロ， インコーポレイテッド Ａｃｃ阻害剤およびその使用
CN106967120A (zh) * 2017-04-24 2017-07-21 贵州大学 含生物碱的磷酸酯类化合物及其制备方法及应用
JP2019503338A (ja) * 2015-11-25 2019-02-07 ギリアド アポロ， エルエルシー ２，４−ジオキソ−１，４−ジヒドロチエノ［２，３−ｄ］ピリミジンの誘導体を含む殺真菌組成物
WO2021085389A1 (ja) * 2019-10-28 2021-05-06 日本曹達株式会社 ２，６－ジオキソ－３，６－ジヒドロピリミジン化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0474170A (ja) * 1990-07-13 1992-03-09 Yamasa Shoyu Co Ltd １―アミノウラシル誘導体
JPH09502178A (ja) * 1993-09-02 1997-03-04 ビーエーエスエフ アクチェンゲゼルシャフト 除草効果を持つ置換１−アミノ−３−フェニルウラシル
JPH11509531A (ja) * 1995-06-29 1999-08-24 ビーエーエスエフ アクチェンゲゼルシャフト 新規な１−アミノ−３−ベンジルウラシル
JP2012053193A (ja) * 2010-08-31 2012-03-15 Nissan Chem Ind Ltd 光配向性の新規な液晶配向剤、及び新規なジアミン化合物
JP2014533281A (ja) * 2011-11-11 2014-12-11 ニンバス アポロ， インコーポレイテッド Ａｃｃ阻害剤およびその使用
JP2019503338A (ja) * 2015-11-25 2019-02-07 ギリアド アポロ， エルエルシー ２，４−ジオキソ−１，４−ジヒドロチエノ［２，３−ｄ］ピリミジンの誘導体を含む殺真菌組成物
CN106967120A (zh) * 2017-04-24 2017-07-21 贵州大学 含生物碱的磷酸酯类化合物及其制备方法及应用
WO2021085389A1 (ja) * 2019-10-28 2021-05-06 日本曹達株式会社 ２，６－ジオキソ－３，６－ジヒドロピリミジン化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BUA SILVIA; OSMAN SAMEH M.; ALOTHMAN ZEID; SUPURAN CLAUDIU T.; NOCENTINI ALESSIO: "Benzenesulfonamides incorporating nitrogenous bases show effective inhibition of β-carbonic anhydrases from the pathogenic fungiCryptococcus neoformans,Candida glabrataandMalassezia globosa", BIOORGANIC CHEMISTRY, ACADEMIC PRESS INC., NEW YORK, NY., US, vol. 86, 1 January 1900 (1900-01-01), US , pages 39 - 43, XP085657585, ISSN: 0045-2068, DOI: 10.1016/j.bioorg.2019.01.030 *
NOVIKOV MIKHAIL S.; VALUEV-ELLISTON VLADIMIR T.; BABKOV DENIS A.; PARAMONOVA MARIA P.; IVANOV ALEXANDER V.; GAVRYUSHOV SERGEY A; K: "N1,N3-disubstituted uracils as nonnucleoside inhibitors of HIV-1 reverse transcriptase", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 21, no. 5, 3 January 2013 (2013-01-03), AMSTERDAM, NL, pages 1150 - 1158, XP028977142, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2012.12.027 *
VYACHESLAV E. SEMENOV; ANATOLY S. MIKHAILOV; ALEXANDRA D. VOLOSHINA; NATALIA V. KULIK; ALEXANDRA D. NIKITASHINA; VLADIMIR V. ZOBOV: "Antimicrobial activity of pyrimidinophanes with thiocytosine and uracil moieties", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 46, no. 9, 13 May 2011 (2011-05-13), AMSTERDAM, NL , pages 4715 - 4724, XP028278379, ISSN: 0223-5234, DOI: 10.1016/j.ejmech.2011.05.034 *

Also Published As

Publication number Publication date
JPWO2023106175A1 (enrdf_load_stackoverflow) 2023-06-15

Similar Documents

Publication Publication Date Title
JP7651464B2 (ja) ２，６－ジオキソ－３，６－ジヒドロピリミジン化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤
KR101994007B1 (ko) 옥심 치환 아미드 화합물 및 유해 생물 방제제
KR20090117639A (ko) 살균제 조성물
JP6508540B2 (ja) ピリジン化合物およびその用途
JP2021008403A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物および農園芸用殺菌剤
JP2021028298A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物および農園芸用殺菌剤
WO2023276813A1 (ja) ピリダジノン化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤
WO2017155052A1 (ja) ピリジン化合物およびその用途
JP2017039722A (ja) アルキニルピリジン置換ピラゾールアミド化合物及び有害生物防除剤
WO2023017699A1 (ja) ３－置換ウラシル化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤
WO2023106175A1 (ja) ウラシル化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤
WO2022224924A1 (ja) 含窒素ヘテロアリール化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤
JP7738656B2 (ja) ピリダジノン化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤
JP2022167333A (ja) ２，６－ジオキソ－３，６－ジヒドロピリミジン化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤
WO2023204124A1 (ja) ピリダジノン化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤
JP2020097575A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物および農園芸用殺菌剤
WO2021054393A1 (ja) ２，３－ジヒドロチエノピリミジン－４（ｈ）－オン化合物および農園芸用殺菌剤
RU2837454C1 (ru) 2,6-диоксо-3,6-дигидропиримидин, сельскохозяйственный и садоводческий бактерицид, нематоцид и медицинское и ветеринарное фунгицидное средство
JP2020147544A (ja) キノリン化合物および農園芸用殺菌剤
JP2019163223A (ja) １，３，５，６−テトラ置換チエノ［２，３−ｄ］ピリミジン−２，４（１Ｈ，３Ｈ）ジオン化合物および農園芸用殺菌剤
JP2023078623A (ja) ３－置換チエノピリミジンジオン化合物を含有する農園芸用殺菌剤
WO2021112213A1 (ja) ２，４－ジオキソ－１，４－ジヒドロチエノピリミジン化合物、及びそれを含有する農園芸用殺菌剤又は医療用・動物用抗真菌剤
JP2021066672A (ja) ピロール化合物を有効成分として含有する農園芸用殺菌剤または医用抗真菌剤
JP2022035834A (ja) ２，４－ジオキソ－１，４－ジヒドロチエノピリミジン化合物及び農園芸用殺菌剤
WO2024143336A1 (ja) ヒドラジド化合物および農園芸用殺菌剤

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 22904106

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2023566261

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 22904106

Country of ref document: EP

Kind code of ref document: A1