WO2021112213A1 - Composé 2,4-dioxo-1,4-dihydrothiénopyrimidine, agent fongicide agricole ou horticole, ou agent antifongique médical/animal le contenant - Google Patents

Composé 2,4-dioxo-1,4-dihydrothiénopyrimidine, agent fongicide agricole ou horticole, ou agent antifongique médical/animal le contenant Download PDF

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WO2021112213A1
WO2021112213A1 PCT/JP2020/045190 JP2020045190W WO2021112213A1 WO 2021112213 A1 WO2021112213 A1 WO 2021112213A1 JP 2020045190 W JP2020045190 W JP 2020045190W WO 2021112213 A1 WO2021112213 A1 WO 2021112213A1
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group
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PCT/JP2020/045190
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Japanese (ja)
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頼人 ▲桑▼原
岩田　淳
拓真 石原
斎賀　睦幸
貴昭 寺西
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日本曹達株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to 2,4-dioxo-1,4-dihydrothienopyrimidine compounds and their uses. More specifically, the present invention provides a 2,4-dioxo-1,4-dihydrothienopyrimidine compound which is excellent in bactericidal activity, is excellent in safety, and can be synthesized industrially advantageously, and an agriculture containing the compound as an active ingredient. Regarding horticultural fungicides or medical / animal antifungal agents. The present application claims priority to Japanese Patent Application No. 2019-220582 filed on December 5, 2019, the contents of which are incorporated herein by reference.
  • Patent Document 1 discloses a compound represented by the formula (A) and the like.
  • Patent Document 2 discloses a compound represented by the formula (B) and the like.
  • Patent Document 3 discloses a compound represented by the formula (C) and the like.
  • Patent Document 4 discloses a compound represented by the formula (D) and the like.
  • Patent Document 5 discloses a compound represented by the formula (E) and the like.
  • Patent Document 6 discloses a compound represented by the formula (F) and the like. Further, Patent Document 7 discloses the use of a fungicide for agriculture and horticulture such as a compound represented by the formula (F).
  • Patent Document 8 discloses a compound represented by the formula (G) and the like.
  • Patent Document 9 discloses a compound represented by the formula (H) and the like.
  • An object of the present invention is that a 2,4-dioxo-1,4-dihydrothienopyrimidine compound (hereinafter, simply referred to as "thienopyrimidine compound”) has excellent bactericidal activity, is excellent in safety, and can be synthesized industrially advantageously. ), And an agricultural and horticultural fungicide or a medical / animal antifungal agent containing the active ingredient.
  • thienopyrimidine compound 2,4-dioxo-1,4-dihydrothienopyrimidine compound
  • a compound represented by the formula (I) or a salt thereof is as follows specified by the following matters.
  • X 1 is a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1 to 6 Alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, Substituted or unsubstituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group
  • R 1 ON CR 6-;
  • R 1 is independently a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a substituted or unsubstituted C3.
  • R 2 each independently represent 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 Representing an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • R 3 are 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 Representing a ⁇ 6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • 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 be combined to form a divalent organic group.
  • 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 represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
  • X 2 is a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1 to 6 Alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, Substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted
  • X 3 , X 4 , X 5 and X 6 each independently represent a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group; X 3 and X 4 may be combined together to form a C2-6 alkylene group; X 4 and X 5 are, which together may form a C2 ⁇ 6 alkylene group; X 5 and X 6 may be combined together to form a C2-6 alkylene group.
  • Q is a group represented by the formula (Q-1) or the formula (Q-2). (In equations (Q-1) and (Q-2), the arrows indicate the binding sites.
  • R c is a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a C1 to 6 alkylamino group, or a substituted or unsubstituted C3 to 6 cycloalkyl group.
  • R d is a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C1 to 6 alkylcarbonyl group.
  • A represents a substituted or unsubstituted C1 to 6 alkylene group, a substituted or unsubstituted C2 to 6 alkenylene group, a substituted or unsubstituted C2 to 6 alkynylene group, or a substituted or unsubstituted C3 to 6 cycloalkylene group.
  • Y represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered ring heterocyclyl group.
  • the substituent on the C1 to 6 alkylene group or C2 to 6 alkenylene group in A is Halogeno groups, substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted Alternatively, an unsubstituted C2 to 6 alkenyloxy group, a substituted or unsubstituted C2 to 6 alkynyloxy group, a mercapto group, a substituted or unsubstituted C1 to 6 alkylthio group, a substituted or unsubstituted C1 to 6 alkylsulfinyl group, a substituted.
  • an unsubstituted C1 to 6 alkylsulfonyl group a substituted or unsubstituted C3 to 6 cycloalkyl group, a substituted or unsubstituted C3 to 6 cycloalkyloxy group, a substituted or unsubstituted C6 to 10 aryl group, a substituted or unsubstituted C6 to 10 aryl group.
  • R b1 independently contains a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, and a substituted or unsubstituted C3 to 6 cyclo.
  • R c1 is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3.
  • R d1 independently represents a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 10 aryl group, where R c1 and R d1 are combined.
  • Divalent organic groups may be formed, Re1 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, a substituted.
  • an unsubstituted C6 to 10 aryl group or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group is shown.
  • R h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, where R g1 and R h1 may be combined to form a divalent organic group; If there are two or more substituents on the C1-6 alkylene group or C2-6 alkenylene group, the two may be combined to form a divalent organic group;
  • R a' is a hydrogen atom or amino group
  • R b' is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • X 2' is a substituted or unsubstituted C1-6 alkyl group.
  • X 3 , X 4 , X 5 and X 6 are independently hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups, respectively.
  • X 3 and X 4 may be combined together to form a C2-6 alkylene group.
  • X 4 and X 5 may be combined together to form a C2-6 alkylene group.
  • X 5 and X 6 may be combined together to form a C2-6 alkylene group.
  • X 7 is a hydroxyl group, a substituted or unsubstituted C1 to 6 alkoxy group or a substituted or unsubstituted C1 to 6 alkylcarbonyloxy group.
  • X 8 is a hydrogen atom.
  • X 7 and X 8 may be combined together to form an oxo group or a substituted or unsubstituted C1-6 alkoxyimino group.
  • X 9 and X 10 are independently hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups.
  • X 8 and X 10 may be combined together to form a single bond.
  • X 11 is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
  • n is an integer of 0 to 5, and when n is 2 or more, X 11 may be the same or different from each other.
  • Q is a group represented by the formula (Q-1) or the formula (Q-2).
  • R c is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, a C1-6 alkylamino group or a substituted or unsubstituted C3-6 cycloalkyl group.
  • R d is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group.
  • X 1 is a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1 to 6 Alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, Substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted
  • R 1 ON CR 6-;
  • R 1 is independently a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a substituted or unsubstituted C3.
  • R 2 each independently represent 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 Representing an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • R 3 are 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 Representing a ⁇ 6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • 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 be combined to form a divalent organic group.
  • 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 represents a hydrogen atom, an amino group, or a substituted or unsubstituted C1-6 alkyl group.
  • X 2 is a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1 to 6 Alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, Substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted
  • X 3 , X 4 , X 5 and X 6 each independently represent a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group; X 3 and X 4 may be combined together to form a C2-6 alkylene group; X 4 and X 5 are, which together may form a C2 ⁇ 6 alkylene group; X 5 and X 6 may be combined together to form a C2-6 alkylene group; Q'indicates a group represented by NH 2 or CH 2 NH 2.
  • A represents a substituted or unsubstituted C1 to 6 alkylene group, a substituted or unsubstituted C2 to 6 alkenylene group, a substituted or unsubstituted C2 to 6 alkynylene group, or a substituted or unsubstituted C3 to 6 cycloalkylene group.
  • Y represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered ring heterocyclyl group.
  • the thienopyrimidine compound of the present invention has excellent bactericidal activity, reliable effect, excellent safety, and can be synthesized industrially advantageously.
  • the agricultural and horticultural fungicide containing the thienopyrimidine compound of the present invention has an excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to humans, livestock and fish and less influence on the environment.
  • the thienopyrimidine compound of the present invention is also useful as an antifungal agent for medical and animal use.
  • the thienopyrimidine compound of the present invention is a compound represented by the formula (I) (hereinafter, may be referred to as a compound (I)) or a salt of the compound (I).
  • compound (II) More preferably, it is a compound represented by the formula (II) (hereinafter, may be referred to as compound (II)) or a salt of compound (II).
  • the term "unsubstituted” means that there are only parental groups. When only the name of the parent group is described, it means “unsubstituted” unless otherwise specified.
  • the term “substituted” means that any hydrogen atom of the parent group is substituted with a group having the same or different structure as the mother nucleus. Therefore, a “substituent” is another group attached to the parent group.
  • the number of substituents may be one or two or more. The two or more substituents may be the same or different.
  • the "substituent” is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
  • groups that can be “substituents” include the following groups. Halogeno groups such as fluoro group, chloro group, bromo group, iod group; 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, etc.
  • Alkyl group Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group , 2-Pentenyl group, 3-Pentenyl group, 4-Pentenyl group, 1-methyl-2-butenyl group, 2-Methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 -C2-6 alkenyl groups such as hexenyl group, 5-hexenyl group;
  • Ethynyl group 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group , 2-Pentynyl group, 3-Pentynyl group, 4-Pentynyl group, 1-methyl-2-butynyl group, 2-Methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc.
  • C2-6 alkynyl group C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; C3-6 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group; C6-10 aryl groups such as phenyl group and naphthyl group; 5-membered heteroaryl group such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isooxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group; A 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a
  • Oxo group C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; C6-10 aryloxy groups such as phenoxy group, naphthoxy group; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups;
  • Carboxyl group Carboxyl group; Holmil group; C1-6 alkylcarbonyl groups such as acetyl and propionyl groups; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group, propionyloxy group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, 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, 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 group; 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
  • Cyano group Nitro group; Amino group; C1-6 alkylamino groups such as methylamino group, dimethylamino group, diethylamino group; C6-10 arylamino groups such as anilino group and naphthylamino group; Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino groups, ethoxycarbonylamino groups, n-propoxycarbonylamino groups, i-propoxycarbonylamino groups; C1-6 alkyl sulfoxide imino groups such as S, S-dimethyl sulfoxide imino groups;
  • Aminocarbonyl group C1-6 alkylaminocarbonyl groups such as methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group, etc.; Imino C1-6 alkyl groups such as iminomethyl group, 1-iminoethyl group, 1-imino-n-propyl group; Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, 1- (hydroxyimino) ethyl group, 1- (hydroxyimino) -n-propyl group; C1-6 alkoxyimino C1-6 alkyl groups such as methoxyiminomethyl group, 1- (methoxyimino) ethyl group;
  • C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group; C2-6 alkenylthio groups such as vinylthio groups and allylthio groups; C2-6 alkynylthio groups such as ethynylthio group and propargylthio group; C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoro
  • Tri-C1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; Tri-C6-10 arylsilyl groups such as triphenylsilyl groups
  • any hydrogen atom in the substituent may be substituted with a group having a different structure.
  • C1 to 6 indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
  • an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the parent group is a butyl group and the substituent is an ethoxy group.
  • X 1 is a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1 to 6 Alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, Substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted
  • R 1 is independently a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a substituted or unsubstituted C3. It represents a ⁇ 6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • R 2 each independently represent 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 It represents an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • R 3 are 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 It represents a ⁇ 6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • R 4 independently represents a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 10 aryl group.
  • R 3 and R 4 may be combined to form a divalent organic group.
  • R 5 independently represents a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 10 aryl group.
  • R 6 represents a hydrogen atom, an amino group or a substituted or unsubstituted C1-6 alkyl group.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, an iod group and the like.
  • the "C1 to 6 alkyl group” in X 1 may be a straight chain or a branched chain.
  • Examples of the "C1 to 6 alkyl group” in X 1 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, and 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 X 1 includes a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and the like.
  • 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 Examples thereof include a group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group and the like.
  • the "C2-6 alkynyl group" in X 1 includes an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, and the like.
  • Examples of the "C1 to 6 alkoxy group" in X 1 include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group and an i-butoxy group. , S-butoxy group, t-butoxy group, i-hexyloxy group and the like.
  • Examples of the "C2 to 6 alkenyloxy group” in X 1 include a vinyloxy group, an allyloxy group, a 1-propenyloxy group, a butenyloxy group and the like.
  • Examples of the "C2 to 6 alkynyloxy group” in X 1 include an ethynyloxy group and a propargyloxy group.
  • Examples of the "C1 to 6 alkylthio group” in X 1 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 to 6 alkylsulfinyl group” in X 1 include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group and the like.
  • Examples of the "C1 to 6 alkylsulfonyl group" in X 1 include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
  • C1 ⁇ 6 alkyl group in X 1, "C2 ⁇ 6 alkenyl group”, “C2 ⁇ 6 alkynyl group”, “C1 ⁇ 6 alkoxy group”, “C2 ⁇ 6 alkenyloxy group”, “C2 ⁇ 6 alkynyloxy
  • a halogeno such as a fluoro group, a chloro group, a bromo group, or an iodo group.
  • Examples of the "C3 to 6 cycloalkyl group” in X 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the "C3 to 6 cycloalkyloxy group” in X 1 include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
  • Examples of the "C6 to 10 aryl group” in X 1 include a phenyl group, a naphthyl group, an indanyl group, an indenyl group, a tetralinyl group and the like.
  • Examples of the "C6 to 10 aryloxy group” in X 1 include a phenoxy group and a naphthoxy group.
  • Examples of the "C6 to 10 arylthio group” in X 1 include a phenylthio group and a naphthylthio group.
  • Examples of the “C6 to 10 arylsulfinyl group” in X 1 include a phenylsulfinyl group and a naphthylsulfinyl group.
  • Examples of the “C6 to 10 arylsulfonyl group” in X 1 include a phenylsulfonyl group and a naphthylsulfonyl group.
  • the "5- to 6-membered heterocyclyl group ring" of X 1, a nitrogen atom, a group containing an oxygen atom and 1, 2, 3 or 4 heteroatoms selected from the group consisting of a sulfur atom as a constituent atom of the ring is there.
  • heteroatoms 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, and a 5- to 6-membered partially unsaturated heterocyclyl group. ..
  • saturated heterocyclyl group having a 5- to 6-membered ring examples include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.
  • Examples of the 5- to 6-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group.
  • a 5-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group and the like
  • the 5- to 6-membered partially unsaturated heterocyclyl group includes a 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group and an oxazolinyl group; an isooxazolinyl group and a dihydro.
  • a 6-membered ring partially unsaturated heterocyclyl group such as a pyranyl group; and the like.
  • 5-6 membered heterocyclyloxy group ring in X 1 is heterocyclyl groups and oxy group having 5 to 6-membered ring having the structure bound. Specific examples include a thiazolyloxy group and a pyridyloxy group.
  • C3 ⁇ 6 cycloalkyl group in X 1, "C3 ⁇ 6 cycloalkyl group”, “C6 ⁇ 10 aryl group”, “C6 ⁇ 10 aryloxy group”, “C6 ⁇ 10 arylthio group”, “C6 ⁇
  • Substituents on the "10 arylsulfinyl group”, “C6-10arylsulfonyl group”, “5-6-membered heterocyclyl group”, or “5-6-membered heterocyclyloxy group” include fluorogroups and chloro groups.
  • Halogeno groups such as bromo group, 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 C1-6 alkyl groups such as groups, n-hexyl groups; C1-6 such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group Haloalkyl group; hydroxyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2- C1-6 haloalkoxy groups such as chloro-n-propoxy group, 2,3-dichlorobut
  • R 1 is a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted group.
  • C1 ⁇ 6 alkyl group in R 1 include methyl group, ethyl group, n- propyl group, n- butyl group, n- pentyl group, n- hexyl, i- propyl, i- butyl, s -Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
  • Examples of the "C2 to 6 alkenyl group” in R 1 include a vinyl group and a 1-propenyl group.
  • Examples of the "C2 to 6 alkynyl group” in R 1 include an ethynyl group and a 1-propynyl group.
  • “C1 ⁇ 6 alkyl group” in R 1 the substituent on the "C2 ⁇ 6 alkenyl” or “C2 ⁇ 6 alkynyl group” refers to fluoro, chloro, bromo group, a halogeno group such as iodo groups; Hydroxyl group; C1-6 alkoxy group such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopen
  • Examples of the "C3 to 6 cycloalkyl group” in R 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the "C6 to 10 aryl group” in R 1 include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.
  • group A "5-6 membered heterocyclyl group ring" in R 1, comprising a nitrogen atom, an oxygen atom and 1, 2, 3 or 4 heteroatoms selected from the group consisting of a sulfur atom as a constituent atom of the ring is there.
  • the "5- to 6-membered heterocyclyl group” include a 5- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group. ..
  • saturated heterocyclyl group having a 5- to 6-membered ring examples include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.
  • Examples of the 5- to 6-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group.
  • a 5-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group and the like
  • the 5- to 6-membered partially unsaturated heterocyclyl group includes a 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group and an oxazolinyl group; an isooxazolinyl group and a dihydro.
  • a 6-membered ring partially unsaturated heterocyclyl group such as a pyranyl group; and the like.
  • Examples of the substituent on the "C3 to 6 cycloalkyl group", “C6 to 10 aryl group", or “5- to 6-membered heterocyclyl group” in R 1 include a fluoro group, a chloro group, a bromo group, and an iodo group. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • C1-6 alkyl groups C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; methoxy group , Ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propoxy group, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group, trifluoromethoxy group; C6-10aryl groups such as phenyl group and naphthyl group; 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-tri A C6-10 aryl group; or a cyano group; substituted with a halogeno group, a C1-6 haloalkyl group, or
  • R 1 -CO- may include formyl group, and acetyl group.
  • R 2 is 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 ring heterocyclyl group.
  • Specific examples of the substituent in R 2 can be the same as those exemplified in R 1.
  • R 2 -O-CO- may include a methoxycarbonyl group and an ethoxycarbonyl group.
  • R 3 is a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or absent.
  • R 4 Indicates a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C6-10 aryl group.
  • R 3 or R 4 can be the same as those exemplified in R 1.
  • R 3 and R 4 may be combined to form a divalent organic group.
  • the divalent organic group that can be formed include substituted or unsubstituted C2 to 5 alkylene groups and substituted or unsubstituted C1 to 3 alkyleneoxy C1 to 3 alkylene groups.
  • Examples of the "C2-5 alkylene group” include a dimethylene group, a trimethylene group, and a tetramethylene group.
  • Examples of the "C1 to 3 alkyleneoxy C1 to 3 alkylene group” include a dimethyleneoxydimethylene group.
  • Examples of the substituent on the "C2-5 alkylene group” or “C1-3 alkyleneoxy C1-3 alkylene group” include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a methyl group, an ethyl group and 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 3 R 4 N- examples include an amino group, a methyl amino group, a dimethyl amino group and the like.
  • R 3 or R 4 has the same meaning as those in the above-mentioned " group represented by R 3 R 4 N-".
  • 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, and an N- (i-propyl) group. ) -N-Methylaminocarbonyl group and the like.
  • R 1 has the same meaning as those in the above " groups represented by R 1-CO-".
  • R 1 -CO-O-a group represented can be mentioned an acetyl group.
  • R 1 has the same meaning as those in the above " groups 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 the substituent in R 5 can be the same as those exemplified in R 1. Specific examples of the "group represented by R 1- CO-NR 5-” include an acetylamino group.
  • R 2 are as defined to those in “group represented by R 2 -O-CO-" above.
  • Specific examples of the “R 2 -O-CO-O- in group represented” may include a methoxycarbonyl group, an ethoxycarbonyl group.
  • R 2 are as defined to those in “group represented by R 2 -O-CO-" above.
  • R 5 has the same meaning as those in the above-mentioned " group represented by R 1- CO-NR 5-".
  • Specific examples of the - "R 2 -O-CO-NR 5 group represented by” may be cited such as methoxycarbonylamino group.
  • R 3 or R 4 has the same meaning as those in the above " group represented by R 3 R 4 N-". Shown. 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 or R 4 has the same meaning as those in the above " group represented by R 3 R 4 N-”. Is shown.
  • R 5 has the same meaning as those in the above-mentioned " 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 SO 2- NR 5- has the same meaning as those in the above " group represented by R 2-O-CO-".
  • R 5 has the same meaning as those in the above-mentioned " 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.
  • R 3 or R 4 has the same meaning as those in the above " group represented by R 3 R 4 N-". .. Specific examples of the "group represented by R 3 R 4 N-SO 2- " include an N, N-dimethylaminosulfonyl group and the like.
  • R 1 is the same meaning as described those in "group represented by R 1 -CO-" above.
  • X 2 is a halogeno group, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1 to 6 Alkoxy groups, substituted or unsubstituted C2-6 alkenyloxy groups, substituted or unsubstituted C2-6 alkynyloxy groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, Substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-6 cycloalkyl groups, substituted or unsubstituted C3-6 cycloalkyloxy groups, substituted or unsubstituted
  • X 3 , X 4 , X 5 , X 6 are independently hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups, respectively.
  • X 3, X 4, the "substituted or unsubstituted C1 ⁇ 6 alkyl group" in X 5 and X 6 may be the same as those that specifically exemplified in the X 1.
  • X 3 and X 4 may be combined to form a C2-6 alkylene group.
  • Examples of the "C2 to 6 alkylene group" formed by X 3 and X 4 together include an ethylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.
  • X 5 and X 6 may be combined to form a C2-6 alkylene group.
  • Examples of the "C2 to 6 alkylene group" formed by X 5 and X 6 together include those similar to those described above.
  • X 4 and X 5 may be combined together to form a C2-6 alkylene group.
  • Examples of the "C2 to 6 alkylene group" formed by X 4 and X 5 together include those similar to those described above.
  • A represents a substituted or unsubstituted C1 to 6 alkylene group, a substituted or unsubstituted C2 to 6 alkenylene group, a substituted or unsubstituted C2 to 6 alkynylene group, or a substituted or unsubstituted C3 to 6 cycloalkylene group. ..
  • Examples of the "C1 to 6 alkylene group” in A include a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group.
  • Examples of the "C2 ⁇ 6 alkynylene group” in A an ethynylene group (-C ⁇ C-), propynylene (-CH 2 -C ⁇ C -, - C ⁇ C -CH 2 -), and the like .
  • Examples of the "C3 to 6 cycloalkylene group” in A include a 1,2-cyclopropylene group, a 1,2-cyclobutanediyl group, and a 1,3-cyclobutanediyl group.
  • preferred A includes a substituted or unsubstituted C1 to 6 alkylene group or a substituted or unsubstituted C2 to 6 alkenylene group.
  • substituent on the C1 to 6 alkylene group or C2 to 6 alkenylene group include one or two or more substituents selected from the following substituent group (hereinafter, this substituent is referred to as the symbol "Ga"). It may be represented by.). When there are two or more substituents (Ga), the two may be combined to form a divalent organic group.
  • the substituent group is shown below.
  • Harogeno groups substituted or unsubstituted C1-6 alkyl groups, substituted or unsubstituted C2-6 alkenyl groups, substituted or unsubstituted C2-6 alkynyl groups, hydroxyl groups, substituted or unsubstituted C1-6 alkoxy groups, substituted Alternatively, an unsubstituted C2-6 alkenyloxy group, a substituted or unsubstituted C2-6 alkynyloxy group, a mercapto group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted.
  • an unsubstituted C1 to 6 alkylsulfonyl group a substituted or unsubstituted C3 to 6 cycloalkyl group, a substituted or unsubstituted C3 to 6 cycloalkyloxy group, a substituted or unsubstituted C6 to 10 aryl group, a substituted or unsubstituted C6 to 10 aryl group.
  • Ra1 is independently a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, and a substituted or unsubstituted C2 to 6 alkynyl. Shows a 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 ring heterocyclyl group.
  • R b1 independently contains a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkynyl group, and a substituted or unsubstituted C3 to 6 cyclo. Representing an alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • R c1 is independently a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a substituted or unsubstituted C3. Representing a ⁇ 6 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered ring heterocyclyl group.
  • R d1 independently represents a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, or a substituted or unsubstituted C6 to 10 aryl group, where R c1 and R d1 are combined. Divalent organic groups may be formed.
  • Re1 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, a substituted.
  • R h1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, where R g1 and R h1 may be combined to form a divalent organic group.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, an iod group and the like.
  • the "C1-6 alkyl group” in Ga may be a straight chain or a branched chain.
  • “C1-6 alkyl groups” in Ga include 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, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, and 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 an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, and 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.
  • Examples of the "C1 to 6 alkoxy group” in Ga include 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. Examples thereof include an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
  • Examples of the "C2 to 6 alkenyloxy group” in Ga include a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group and the like.
  • Examples of the "C2 to 6 alkynyloxy group” in Ga include an ethynyloxy group and a propargyloxy group.
  • Examples of the "C1 to 6 alkylthio group” in Ga include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group and the like.
  • Examples of the "C1 to 6 alkylsulfinyl group” in Ga include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group and the like.
  • Examples of the "C1 to 6 alkylsulfonyl group" in Ga include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
  • 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 Ga , "C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, or “C1-6 alkylsulfonyl group” as a substituent on a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group.
  • C1-6 alkoxy group such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro- C1-6 haloalkoxy groups such as n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; phenyl group, C6-10aryl groups such as naphthyl groups; C1-6 alkyl groups such as 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group. , C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or
  • Examples of the "C3 to 6 cycloalkyl group” in Ga include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the "C3 to 6 cycloalkyloxy group” in Ga include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
  • Examples of the "C6 to 10 aryl group” in Ga include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.
  • Examples of the "C6 to 10 aryloxy group” in Ga include a phenoxy group and a naphthoxy group.
  • Examples of the "C6 to 10 arylthio group” in Ga include a phenylthio group and a naphthylthio group.
  • Examples of the “C6 to 10 arylsulfinyl group” in Ga include a phenylsulfinyl group and a naphthylsulfinyl group.
  • Examples of the “C6 to 10 arylsulfonyl group” in Ga include a phenylsulfonyl group and a naphthylsulfonyl group.
  • the "3- to 6-membered ring heterocyclyl group" in Ga is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent atoms. .. When there are two or more heteroatoms, they may be the same or different.
  • Examples of the "3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group. ..
  • Examples of the saturated heterocyclyl group having a 3- to 6-membered ring include an aziridinyl group, an epoxy group, an azetidinyl group, an oxetanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group and a morpholinyl group. Examples thereof include a dioxolanyl group and a dioxanyl group.
  • the 5- to 6-membered heteroaryl group includes a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group.
  • 5-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group and the like.
  • the 5- to 6-membered partially unsaturated heterocyclyl group includes a 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group and an oxazolinyl group; an isooxazolinyl group and a dihydro.
  • a 6-membered ring partially unsaturated heterocyclyl group such as a pyranyl group can be mentioned.
  • the "3- to 6-membered ring heterocyclyloxy group" in Ga has a structure in which a 3- to 6-membered ring 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”, “C6-10” in Ga
  • Substituents on the "arylsulfinyl group”, “C6-10arylsulfonyl group”, “3-6-membered ring heterocyclyl group”, or “3-6-membered ring heterocyclyloxy group” include fluorogroups, chloro groups, Halogeno groups such as bromo group and iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group.
  • C1-6 alkyl groups such as n-hexyl group
  • C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group Group
  • hydroxyl group C1-6 alkoxy group such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group
  • 2-chloro C1-6 haloalkoxy groups such as -n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group
  • C6-10 aryl groups such as phenyl group and naphthyl group
  • R a1 represents 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 ring heterocyclyl group.
  • Examples of the "C1 to 6 alkyl group” in Ra1 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, and s.
  • -Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
  • Examples of the "C2 to 6 alkenyl group” in Ra1 include a vinyl group and a 1-propenyl group.
  • Examples of the "C2 to 6 alkynyl group” in Ra1 include an ethynyl group and a 1-propynyl group.
  • "C1 ⁇ 6 alkyl group” in R a1 as a substituent on “C2 ⁇ 6 alkenyl” or “C2 ⁇ 6 alkynyl group” refers to fluoro, chloro, bromo group, a halogeno group such as iodo groups; Hydroxyl group; C1-6 alkoxy group such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n -C1-6 haloalkoxy groups such as propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group,
  • Examples of the "C3 to 6 cycloalkyl group” in Ra 1 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • Examples of the "C6 to 10 aryl group” in Ra1 include a phenyl group and a naphthyl group.
  • group A "5-6 membered heterocyclyl group ring" in R a1 containing nitrogen atom, oxygen atom and 1, 2, 3 or 4 heteroatoms selected from the group consisting of a sulfur atom as a constituent atom of the ring is there. 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, and a 5- to 6-membered partially unsaturated heterocyclyl group. ..
  • Examples of the saturated heterocyclyl group having a 5- to 6-membered ring include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.
  • the 5- to 6-membered heteroaryl group includes a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group.
  • 5-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group and the like.
  • the 5- to 6-membered partially unsaturated heterocyclyl group includes a 5-membered partially unsaturated heterocyclyl group such as a pyrrolinyl group, a dihydrofuranyl group, an imidazolinyl group, a pyrazolinyl group and an oxazolinyl group; an isooxazolinyl group and a dihydro.
  • a 6-membered ring partially unsaturated heterocyclyl group such as a pyranyl group can be mentioned.
  • Examples of the substituent on the "C3 to 6 cycloalkyl group", “C6 to 10 aryl group", or “5- to 6-membered heterocyclyl group” in Ra 1 include a fluoro group, a chloro group, a bromo group, and an iodo group. Halogeno group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
  • C1-6 alkyl groups C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; hydroxyl group; methoxy group , Ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propoxy group, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group, trifluoromethoxy group; C6-10aryl groups such as phenyl group and naphthyl group; 4-methylphenyl group, 4-methoxyphenyl group, 4-chlorophenyl group , 4-Trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, C1-6 alkyl group, C1-6 alkoxy group,
  • R a1 -CO- may include formyl group, and acetyl group.
  • R b1 is a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2. It represents a ⁇ 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 ring heterocyclyl group.
  • Specific examples of the substituent in R b1 can be the same as those exemplified in 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 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, a substituted or unsubstituted C2 to 6 alkenyl group.
  • R d1 is , Hydrogen atom, substituted or unsubstituted C1-6 alkyl group, or substituted or unsubstituted C6-10 aryl group.
  • R c1 and R d1 may be combined to form a divalent organic group.
  • Examples of the divalent organic group that can be formed include substituted or unsubstituted C2 to 5 alkylene groups and substituted or unsubstituted C1 to 3 alkyleneoxy C1 to 3 alkylene groups.
  • Examples of the "C2-5 alkylene group” include a dimethylene group, a trimethylene group, and a tetramethylene group.
  • Examples of the "C1 to 3 alkyleneoxy C1 to 3 alkylene group” include a dimethyleneoxydimethylene group.
  • Examples of the substituent on the "C2-5 alkylene group” or “C1-3 alkyleneoxy C1-3 alkylene group” include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a methyl group, an ethyl group and 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 c1 R d1 N- examples include an amino group, a methylamino group, a dimethylamino group and the like.
  • R c1 and R d1 have the same meanings as those in the above-mentioned " 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) group. ) -N-Methylaminocarbonyl group and the like.
  • R a1 represents a similar meaning in “group represented by R a1 -CO-" above.
  • Specific examples of the “R a1 -CO-O- a group represented” can be mentioned an acetyl group.
  • R a1 has the same meaning as that in the above-mentioned " Group represented by R a1-CO-".
  • Re1 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 in R e1 may be the same as those exemplified in Ra1.
  • Specific examples of the "group represented by R a1- CO-NR e1- " include an acetylamino group and the like.
  • R b1 has the same meaning as that in the above-mentioned "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 that in the above-mentioned " Group represented by R b1-O-CO-”.
  • R e1 has the same meaning as that in the above-mentioned " group represented by R a1- 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-".
  • R e1 has the same meaning as that in the above-mentioned " 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, an N, N-dimethylaminocarbonylamino group and the like.
  • R b1 has the same meaning as that in the above-mentioned " Group represented by R b1-O-CO-”.
  • R e1 has the same meaning as that in the above-mentioned " 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.
  • 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 and the like.
  • R a1 represents a similar meaning in "group represented by R a1 -CO-" above.
  • R g1 is a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, substituted or absent. Shows 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. Indicates a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
  • R g1 or R h1 can be the same as those exemplified in Ra1.
  • R g1 and R h1 may be combined to form a divalent organic group.
  • the divalent organic group that can be formed include substituted or unsubstituted C2 to 5 alkylene groups and substituted or unsubstituted C1 to 3 alkyleneoxy C1 to 3 alkylene groups.
  • Examples of the "C2-5 alkylene group” include a dimethylene group, a trimethylene group, and a tetramethylene group.
  • Examples of the "C1 to 3 alkyleneoxy C1 to 3 alkylene group” include a dimethyleneoxydimethylene group.
  • Examples of the substituent on the "C2-5 alkylene group” or “C1-3 alkyleneoxy C1-3 alkylene group” include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a methyl group, an ethyl group and 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 that in the above-mentioned " group represented by R a1-CO-".
  • R a1 represents a similar meaning in “group represented by R a1 -CO-" above.
  • R a1 has the same meaning as that in the above-mentioned " group represented by R a1-CO-”.
  • R e1 has the same meaning as that in the above-mentioned " group represented by R a1- CO-NR e1-”.
  • R b1- O-CO-NR e1- N in Ga
  • R b1 has the same meaning as that in the above " group represented by R b1-O-CO-”. Is shown.
  • R e1 has the same meaning as that in the above-mentioned " group represented by R a1- CO-NR e1-".
  • R b1 SO 2- NR e1- N in Ga
  • R b1 has the same meaning as that in the above " group represented by R b1-O-CO-”.
  • R e1 has the same meaning as that in the above-mentioned " group represented by R a1- CO-NR e1-".
  • the divalent organic groups that can be formed by combining the two are C1 to 5 alkylene groups substituted or unsubstituted, and oxy C1 to 4 substituted or unsubstituted.
  • Examples thereof include an alkylene group, a substituted or unsubstituted oxy C2 to 3 alkylene oxy group, and a substituted or unsubstituted C1 to 3 alkylene oxy C1 to 3 alkylene group.
  • Examples of the "C1-5 alkylene group” include a methylene group, a dimethylene group, a trimethylene group, a 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 to 3 alkyleneoxy group” include an oxydimethyleneoxy group.
  • Examples of the “C1 to 3 alkyleneoxy C1 to 3 alkylene group” include a dimethyleneoxydimethylene group.
  • Substituents on "C1-5 alkylene group”, “oxy C1-4 alkylene group”, “oxy C2-3 alkyleneoxy group”, “C1-3 alkyleneoxy C1-3 alkylene group” include fluorogroup and chloro.
  • Halogeno groups such as groups, bromo groups and iodo groups; C1 such as methyl groups, ethyl groups, n-propyl groups, i-propyl groups, n-butyl groups, s-butyl groups, i-butyl groups and t-butyl groups. ⁇ 6 Alkyl groups; or C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group are preferable.
  • preferred Ga is a hydroxyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a substituted or unsubstituted C2 to 6 alkenyloxy group, a substituted or unsubstituted C2 to 6 alkynyloxy group, a substituted or unsubstituted C1 to 6 alkoxy group.
  • the preferred substituted or unsubstituted 5- to 6-membered ring heterocyclyloxy group may include a tetrahydro-2H-pyran-4-yl group.
  • more preferable Gas include a hydroxyl group, a substituted or unsubstituted C1 to 6 alkoxy group, a substituted or unsubstituted C2 to 6 alkenyloxy group, a substituted or unsubstituted C2 to 6 alkynyloxy group, and Ra1 ⁇ .
  • Y represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered ring heterocyclyl group.
  • Examples of the "C6 to 10 aryl group" in Y include a phenyl group, a naphthyl group, an indenyl group, an indanyl group, a tetralinyl group and the like.
  • the "5- to 10-membered ring heterocyclyl group" in Y is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent 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, and a 5- to 10-membered partially unsaturated heterocyclyl group. ..
  • Examples of the saturated heterocyclyl group having a 5- to 6-membered ring include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.
  • the heteroaryl group having a 5- to 10-membered ring includes a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group.
  • 5-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyrariainyl group, triazinyl group and other 6-membered heteroaryl group; indolyl group, isoindryl group, benzofuranyl group, benzothienyl group, indazolyl group,
  • Nine-membered heteroaryl groups such as benzoimidazolyl group, benzoxazolyl group, benzoisooxaozolic group, benzothiazolyl group, benzoisothiazolyl group; quinolinyl group, isoquinolinyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, etc.
  • the 5- to 10-membered partially unsaturated heterocyclyl group includes a 5-membered partially unsaturated heterocyclyl group such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group and oxazolinyl group; isooxazolinyl group and dihydro.
  • Partially unsaturated 6-membered ring such as pyranyl group Heterocyclyl group; partially unsaturated 9-membered ring such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group Heterocyclyl groups; partially unsaturated heterocyclyl groups with 10-membered rings such as 1,2,3,4-tetrahydroquinolinyl groups; can be mentioned.
  • Substituents on the "C6 to 10 aryl group” or “5 to 10-membered heterocyclyl group” in Y include halogeno groups such as fluoro group, chloro group, bromo group, and iodo group; methyl group, ethyl group, and the like.
  • C1-6 alkyl groups such as n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; vinyl group, etc.
  • C2 to 6 alkoxy groups such as ethynyl groups; chloromethyl groups, chloroethyl groups, trifluoromethyl groups, 1,2-dichloro-n-propyl groups, 1-fluoro-n-butyl groups, etc.
  • C1-6 haloalkyl groups C1-6 alkoxy C1-6 alkyl groups such as methoxymethyl groups; hydroxyl groups; methoxy groups, ethoxy groups, n-propoxy groups, i-propoxy groups, n-butoxy groups, s-butoxy groups, i -C1-6 alkoxy groups such as butoxy group and t-butoxy group; hydroxy C1-6 alkoxy groups such as hydroxyethoxy group; C1-6 alkoxyalkoxy groups such as methoxymethoxy group and methoxyethoxy group; trimethylsilyloxyethoxy group, t -Tri-C1-6 alkyl-substituted silyloxy C1-6 alkoxy groups such as butyldimethylsilyloxyethoxy group; C1-6 haloalkoxy such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group Group; C3-6 cycloalkyl C1-6 alkoxy group; C6-10ary
  • C6-10aryl group substituted with any one or more substituents of a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; 3-4 such as an aziridinyl group, an epoxy group, an azetidineyl group, an oxetanyl group, etc. Saturated heterocyclyl group of member ring; 3-4 substituted with any one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group.
  • Saturated heterocyclyl group of member ring saturated heterocyclyl group of 5-6 member ring such as pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, tetrahydro-2H-pyranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group;
  • 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1- 6-membered ring heteroaryl group substituted with any one or more substituents of 6 haloalkyl group or C1-6 haloalkoxy group; 5 such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group and the like.
  • Partially unsaturated heterocyclyl group of member ring substituted with any one or more substituents of C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group.
  • R Y1 together be the same or different, together, trimethylene group, tetramethylene group, may form a pentamethylene group, or a di-methyleneoxy dimethylene group).
  • R Y1 -O-N C ( R Y4) - (.
  • Q is a group represented by formula (Q-1) or formula (Q-2).
  • R c is a hydrogen atom, a substituted or unsubstituted C1 to 6 alkyl group, a substituted or unsubstituted C1 to 6 alkoxy group, and a C1 to 6 alkylamino group. Alternatively, it is a substituted or unsubstituted C3 to 6 cycloalkyl group.
  • R d is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, or a substituted or unsubstituted C1-6 alkylcarbonyl group.
  • R c and R d examples include the same ones specifically exemplified in X 1' , and "substituted or unsubstituted C1 to 6 alkoxy" can be mentioned.
  • Examples of the "C1 to 6 alkylamino group” in Rc include a methylamino group, a dimethylamino group, a diethylamino group and the like.
  • a substituent on "C1 ⁇ 6 alkylamino group” in R c preferably, mention may be made of C1 ⁇ 6 alkyl group.
  • Examples of the “C1 to 6 alkyl groups” include the same ones specifically exemplified in R 1.
  • Examples of the "C3 to 6 cycloalkyl group" in R c include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • a substituent on "C3 ⁇ 6 cycloalkyl group” in R c preferably fluoro, chloro, bromo group, a halogeno group such as iodo groups; and a cyano group.
  • Examples of the "C1 to 6 alkylcarbonyl group” in R d include an acetyl group, a propionyl group, an isopropylcarbonyl group and the like.
  • a substituent on "C1 ⁇ 6 alkyl group” in R d preferably fluoro, chloro, bromo group, a halogeno group such as iodo groups; and a cyano group.
  • Examples of the “C1 to 6 alkoxycarbonyl group” in X 1 ′ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, a t-butoxycarbonyl group, and the like. Can be done.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be preferably mentioned.
  • C1 ⁇ 6 alkyl group in X 1 ' are members independently selected from methyl, ethyl, n- propyl, n- butyl, n- pentyl, n- hexyl, i- propyl, i- butyl group, Examples thereof include s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group and i-hexyl group.
  • a C1 to 6 alkoxy group such as a hydroxyl group; a methoxy group or an ethoxy group can be mentioned.
  • 6-membered heteroaryl group in X 1 'are members independently selected from a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl 5-membered heteroaryl groups such as groups and tetrazolyl groups; 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group and triazinyl group can be mentioned.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be preferably mentioned.
  • Alkyl groups include 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 and t-butyl group. , I-Pentyl group, Neopentyl group, 2-Methylbutyl group, i-Hexyl group and the like.
  • a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group is preferable; a methoxy group, an ethoxy group, an n-propoxy group and an i-propoxy group. , N-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group and the like.
  • C1-6 haloalkoxy groups; cyano groups can be mentioned.
  • X 7 is a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group or a substituted or unsubstituted C1-6 alkylcarbonyloxy group.
  • the "C1 ⁇ 6 alkoxy group" in X 7, a methoxy group, an ethoxy group, n- propoxy group, i- propoxy, n- butoxy, s- butoxy group, i- butoxy group, and the like t- butoxy Can be mentioned.
  • a substituent on "C1 ⁇ 6 alkoxy group” and "C1 ⁇ 6 alkyl-carbonyl group” in X 7, preferably fluoro, chloro, bromo group, a halogeno group such as iodo group; methoxy group, an ethoxy group C1 to 6 alkoxy groups; cyano groups can be mentioned.
  • X 8 is a hydrogen atom.
  • X 7 and X 8 may be combined together to form an oxo group or a substituted or unsubstituted C1-6 alkoxyimino group.
  • Examples of the "C1 to 6 alkoxyimino group" formed by X 7 and X 8 together include a methoxyimino group and an ethoxyimino group.
  • Preferred examples of the substituent on the "C1 to 6 alkoxyimino group" formed by X 7 and X 8 together include a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group.
  • X 9 and X 10 are independently hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups.
  • X 8 and X 10 may be combined together to form a single bond.
  • Formula (III) can be mentioned as a compound forming a single bond.
  • the symbols of X 1' , X 2' , X 3 , X 4 , X 5 , X 6 , X 7 , X 9 , X 11 , n, and Q in the formula (III) are the symbols of the formula (II). Means the same as that of.
  • X 11 is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
  • halogeno group examples include a fluoro group, a chloro group, a bromo group, an iod group and the like.
  • substituted or unsubstituted C1 to 6 alkoxy groups examples include the same groups specifically exemplified in X 7.
  • n is an integer of 0 to 5, and when n is 2 or more, X 11 may be the same or different from each other.
  • salts of compound (I) and compound (II) are not particularly limited as long as they are 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
  • iron, copper and the like Transition metal salts
  • salts of organic bases such as triethylamine, tributylamine, pyridine, hydrazine; ammonia and the like.
  • the method for producing the compound (I) and the compound represented by the compound (II) or a salt thereof is not limited.
  • the compound (I) and the compound represented by the compound (II) of the present invention or a salt thereof can be obtained by a known method as described in Examples and the like.
  • the salts of compound (I) and compound (II) can be obtained from compound (I) and compound (II) by a known method.
  • Table 1 shows an example of the production intermediate used for producing the compound (I) and the compound (II) of the present invention.
  • the melting point (m.p.) is also shown as the physical characteristics of each compound.
  • the agricultural and horticultural fungicide of the present invention contains at least one selected from the group consisting of the compound represented by the compound (I) and the compound (II) or a salt thereof as an active ingredient.
  • the amount of the compound (I) and the compound represented by the compound (II) or a salt thereof contained in the bactericidal agent for agriculture and horticulture of the present invention is not particularly limited as long as it exhibits a bactericidal effect.
  • the agricultural and horticultural fungi of the present invention include a wide variety of filamentous fungi, such as algae fungi (Oomycetes), ascomycetes (Ascomycetes), imperfecti fungi (Deuteromycetes), basidiomycetes, and zygomycetes. It can be used to control plant diseases derived from fungi belonging to fungi (Zygomycetes).
  • Cercospora beticola black root disease (Aphanomyces cochlioides), root rot (Thanatephorus cucumeris), leaf rot (Thanatephorus cucumeris), rust (Uromyces betae), powdery mildew (Oidium sp.), Spots Diseases (Ramularia beticola), seedling blight (Aphanomyces cochlioides, Pythium ultimum), etc.
  • Cercospora beetle Alternaria alternata
  • white silk disease Sclerotium rolfsii
  • black astringent disease Mycosphaerella berkeleyi
  • black root rot Calonectria ilicicola
  • Mycosphaerella melonis Fusarium oxysporum, Sclerotis sclerotiorum, Botrytis cinerea, Colletotrichum orbiculare, Cladosporium cucumerinum Diseases (Corynespora cassiicola), seedling blight (Pythium debaryanum, Rhizoctonia solani Kuhn), homopsis sp., Pseudomonas syringae pv. Lachrymans, etc.
  • Tomatoes Botrytis cinerea, leaves Mold disease (Cladosporium fulvum), plague (Phytophthora infestans), half-body wilt disease (Verticillium albo-atrum, Verticillium dahliae), powdery mildew (Oidium neolycopersici), ring stain (Alternaria solani), Botrytis cinerea, Botrytis cinerea, Corynespora melongenae, Erysiphe, etc.
  • Botrytis cinerea Erysiphe cichoracearum
  • Botrytis cinerea Botrytis cinerea (Mycovellosiella nattrassii)
  • Botrytis cinerea Botrytis cinerea (Sclerotinia sclerotiorum)
  • Botrytis cinerea Verticillium dahliae
  • Botrytis cinerea Botrytis cinerea (Phomopsis vexans), etc.
  • Botrytis cinerea Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, etc.
  • Botrytis cinerea Coldhousetrichum acutatum, Colletrichum fragariae
  • plague Phytophthora cactorum
  • soft rot Rhizopus stolonifer
  • cinerea Feusarium oxysporum
  • wilt Verticillium dahliae
  • Botrytis allii Botrytis cinerea, Botrytis cinerea, Peronospora destructor, Phytophthora porri, Ciborinia allii, small fungus Botrytis cinerea, Botrytis oxysporum, Botrytis cinerea, Botrytis cinerea (Pyrenochaeta terrestris) Sclerotium cepivorum, Puccinia allii, Sclerotium rolfsii, etc.
  • Negi Pectobacterium carotovorum, Peronospora destructor, Pleospora allii, Sclerotinia sclerotinia (Pleospora allii) Sclerotinia cepivorum, Puccinia allii, Botrytis cinerea, Sclerotium rolfsii, Pyrenochaeta terrestris, etc.
  • Cabbets cinerea (Plasmodiophora brassicae), soft rot (Plasmodiophora brassicae) Erwinia carotovora), Botrytis cinerea (Xanthomonas campesrtis pv. Campestris), Botrytis cinerea pv.
  • Maculicola P. s. Pv. Alisalensis, Peronospora parasitica, Sclerotiorum , Black sclerotinia (Alternaria brassicicola), Botrytis cinerea, Phoma lingam, Pythium aphanidermatum, Pythium ultimum, etc.
  • Botrytis cinerea (Podosphaera leucotricha), Botrytis cinerea (Venturia inaequalis), Monilinia mali, Mycosphaerella pomi, Botrytis cinerea (Valsa mali), Botrytis cinerea (Alternaria mali), Botrytis cinerea (Gymnosporang) yamadae), Botryosphaeria berengeriana, Botrytis cinerea, Botrytis cinerea, Colletotrichum acutatum, Diplocarpon mali, Zygophiala jamaicensis, Gloeodes pomigena, Botrytis cinerea (Helicobasidium mompa), white crest disease (Rosellinia necatrix), Botrytis cinerea, burn disease (Erwinia amylovora), silver leaf disease (Chondrostereum purpureum), root cancer radiobacter (Rhizobium rhizogenes) Um
  • Pestalotiops is longiseta, P.
  • Kiwi fruit flower rot bacterial disease (Pseudomonas marginalis, Pseudomonas syringae, Pseudomonas viridiflava), scab (Pseudomonas syringae), gray mold (Botryosphaeria dothidea, Diaporthe sp., Lasiodiplodia theobromae), Pseudocercospora actinidiae, etc.
  • Olive Colletotrichum acutatum, Colletotrichum gloeosporioides, Peacock spot (Spilocaea oleaginea), etc.
  • Udonko disease (Blumeria graminis f.sp. Tritici), red mold disease (Gibberella zeae, Fusarium avenaceum, Fusarium culmorum, Fusarium crookwellense, Microdochium nivale), red rust disease (Puccinia recondita), yellow rust (Puccinia recondita), yellow rust (Puccinia recondita) Brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eye print disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow rot small granule nuclear disease (Typhula) incarnata), Myriosclerotinia borealis, Gaeumannomyces graminis, Claviceps purpurea, Tilletia car
  • Botrytis cinerea (Sclerotinia sclerotiorum), Erysiphe cichoracearum Phytophthora nicotianae), etc.
  • Tutu Botrytis cinerea, Botrytis tulipae, Rhizoctonia solani, Fusarium oxysporum, Rhizoctonia solani, etc.
  • Rose Black star Disease (Diplocarpon rosae), Botrytis cinerea (Erysiphe simulans, Podosphaera pannosa), Botrytis cinerea, etc.
  • Kiku Botrytis cinerea, Puccinia horiana, Paraperonospora minor, Peronospora danica, Pythium aphanidermatum, Pythium dissotocum, Pythium helicoides, Pythium oedochilum, Pythium sylvaticum, Rhizoctonia solani, Botrytis cinerea, Botrytis cinerea, etc. ), Botrytis cinerea, etc.
  • Yuri Leaf blight (Botrytis elliptica, Pestalotiopsis sp.), Botrytis cinerea, etc.
  • Sunflower Botrytis cinerea (Pl) asmopara halstedii), sclerotinia sclerotiorum, Botrytis cinerea, etc.
  • Bentgrass Sclerotinia borealis, Rhizoctonia solani, Rhizoctonia solani, dollar spot (Rhizoctonia solani) Sclerotinia homoeocarpa), blast (Pyricularia sp.), Red burning disease (Pythium aphanidermatum), charcoal illness (Colletotrichum graminicola), etc.
  • Orchardgrass Udonko disease (Erysiphe graminis), etc.
  • Ginger Rhizome ultimum, Pythium myriotylum, Phyllosticta zingiberis, etc.
  • Banana Panama disease (Fusarium oxysporum), Black sigatoka disease (Mycosphaerella fijiensis, M. musicola), etc.
  • Mango Charcoal aenigma), Panama disease (Xanthomonas campestris), Axial rot (Diaporthe pseudophoenicicola, Lasiodiplodia theobromae, Lasiodiplodia spp., Neofusicoccum parvum, Neofusicoccum sp.), Gray mold (Botrytis cinerea), etc.
  • Phoma lingam Alternaria brassicae, Udonko disease (Erysiphe cruciferarum, Erysiphe cichoracearum, Oidium matthiolae), Peronospora parasitica, etc.
  • Coffee rust (Hemileia vastatrix), charcoal disease (Hemileia vastatrix) Colletotrichum coffeanum, brown eye disease (Cercospora coffeicola), etc.
  • the agricultural and horticultural bactericide of the present invention is used for grains; vegetables; root vegetables; potatoes; fruit trees, tea, coffee, cacao and other trees; pastures; turf; cotton and other plants. Is preferable.
  • the agricultural and horticultural bactericide of the present invention can be applied to various parts of plants, for example, leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tubers, shoots, cuttings and the like. ..
  • improved varieties / varieties of these plants, cultivars, mutants, hybrids, and genetically modified organisms (GMOs) can also be targeted.
  • the fungicide for agriculture and horticulture of the present invention shall be used for seed treatment, foliage spraying, soil application, water surface application, etc., which are performed to control various diseases occurring in agricultural and horticultural crops including flowers, turf, and grass. Can be done.
  • the agricultural and horticultural fungicide of the present invention may contain components other than the thienopyrimidine compound of the present invention.
  • other components include known carriers used for formulation.
  • conventionally known fungicides, insecticides / acaricides, nematode insecticides, soil pesticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds and the like can be mentioned. be able to. By containing such other components, a synergistic effect may be produced.
  • Nucleic acid biosynthesis inhibitor (A) RNA polymerase I inhibitor: Benalaxil, Benalaxil-M, Flaluxil, Metalaxil, Metalaxil-M; Oxadixil; Crodiracon, Offrace; (B) Adenosine deaminase inhibitors: bupirimate, dimethyrimole, etilimol; (C) DNA / RNA synthesis inhibitors: himexazole, octinenone; (D) DNA topoisomerase II inhibitor: oxolinic acid.
  • Mitotic and fission inhibitors (A) ⁇ -tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; etaboxam; (B) Cell division inhibitor: pencyclon; (C) Inhibitors for delocalization of spectrin-like proteins: fluoricorid, fluopimomid.
  • Respiratory inhibitor (A) Complex I-NADH Oxidoreductase Inhibitor: Diflumetrim; Torfenpyrad; (B) Complex II-succinate dehydrogenase inhibitors: benodanyl, flutranyl, mepronil; isofetamide; fluopirum; fenfurum, flumecyclox; carboxin, oxycarboxyne; thyfluzamide; benzobindiflupill, bixafene, fluxapiroki Sad, flametopil, isopyrazam, penflufen, penthiopyrado, sedaxan; boscalide, pidiflumethophene, isoflusifram, pyraziflumid, impyrfluxam, pyrapropoyne; (C) Complex III-ubiquinol oxidase Qo inhibitor: azoxystrobin, spideristrobin, kumethoxystrobin, enoxastrobin, fluor
  • Amino acid and protein synthesis inhibitors (A) Methionine biosynthesis inhibitors: andprim, cyprodinyl, mepanipyrim, pyrimethanyl; (B) Protein synthesis inhibitor: Blasticidin-S, casugamycin, casugamycin hydrochloride, streptomycin, oxytetracycline.
  • Signal transduction inhibitor (A) Signal transduction inhibitors: quinoxyphen, proquinazide; (B) MAP / histidine kinase inhibitors in osmotic signal transduction: fenpicronyl, fludioxonyl; clozolinate, iprodion, procymidone, vinclozoline.
  • Lipid and cell membrane synthesis inhibitor (A) Phospholipid biosynthesis, methyltransferase inhibitor: edifenephos, iprobenphos, pyrazophos; isoprothiolane; (B) Lipid peroxidizers: biphenyl, chloroneb, dichlorolane, quintozen, technazen, turquophosmethyl; etridiazole; (C) Agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb hosetylate, prothiocarb; (D) Pathogens Microorganisms that disturb cell membranes: Bacillus subtilis, Bacillus tinbutiris QST713 strain, Bacillus tinbutiris FZB24 strain, Bacillus tinbutiris MBI600 strain, Bacillus tinbutiris D747 strain; (E) Agent that disturbs cell membranes: Extract of Gosei Kay
  • Cell membrane sterol biosynthesis inhibitor (A) Demethylation inhibitor at position C14 in sterol biosynthesis: trifoline; pyriphenox, pyrisoxazole; phenalimol, fluconazole, nuarimol; imazalyl, imazalyl sulfate, oxypoconazole, pefrazoate, prochloraz, fluconazole , Biniconazole; azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, diphenoconazole, diniconazole, diniconazole-M, epoxyconazole, etaconazole, fenbuconazole, fluconazole, fluconazole, fluconazole, fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole
  • Cell wall synthesis inhibitor (A) Trehalase inhibitor: validamycin; (B) Chitin synthase inhibitors: polyoxine, polyoxolim; (C) Cellulose Synthetic Enzyme Inhibitors: Dimethmorph, Fulmorph, Pyrimorph; Bench Avaricarb, Iprovaricarb, Variphenalate; Mandipropamide.
  • Melanin biosynthesis inhibitor (a) Melanin biosynthesis reductase inhibitor: fusalide; pyrokyron; tricyclazole; (B) Dehydrating enzyme inhibitor of melanin biosynthesis: calpropamide; diclosimet; phenoxanyl; (C) Inhibitor of melanin biosynthesis polyketide synthesis: toluprocarb.
  • Host plant resistance inducer (A) Agent acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl; (B) Others: probenazole, thiazinyl, isothianil, diclobenazox, ipfentrifluconazole, laminarin, Reynoutria sachalinensis extract.
  • Agents of unknown activity simoxanyl, Josetylaluminum, phosphate (phosphate), tecrophthalam, triazoxide, flusulfamide, dichromedin, metasulfocarb, ciflufenamide, metrafenone, pyriophenone, dodine, dodine free base, fluthianyl.
  • Agents having multiple points of action copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; Man copper, methylam, polycarbamate, propineb, tiram, dineb, dilam; captan, captahole, folpet; chlorotalonyl; diclofluanide, trillfluanide; guazatin, guazatin acetate, iminoctadine triacetate, iminoctadine albe Iminoctadine trialbesilate; anilazine; dithianone; quinomethionate; fluorimide.
  • insecticides / acaricides, nematodes, soil pesticides, anthelmintics, etc. that can be mixed or used in combination with the agricultural and horticultural fungicides of the present invention are shown below.
  • Acetylcholinesterase (AChE) inhibitor (carbamate type): (1A) Alanicarb, Aldicarb, Bendiocarb, Benfracarb, Butocarboxim, Butoxycarboxym, Carbaryl, Carbofuran, Carbosulfan, Ethiophenacarb, Phenoccarb, Formetanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamil, Pyrimicurve, Propoxil , Thiodicarb, thiofanox, triazamate, trimetacarb, XMC, xylylcarb; MIPC, MPMC, MTMC; aldicarb, alixicalve, aminocarb, butocarboxim, chloroecalve, phenothiocarb, promecarb.
  • AChE Acetylcholinesterase
  • GABAergic chloride ion (chlorine ion) channel blocker acetoprol, chlordane, endosulfan, ethiprol, fipronil, pilafrol, piriprol, campechlor, heptachlor, dienochlor, fulfiprol.
  • ⁇ -Bifentrin biopermethrin, chloropralesrun, dimefluthrin, fenfluthrin, fenpyritrin, flufenprox, heptafluthrin, mepermethrin, ⁇ -methfurthrin, monfluorothrin, ⁇ -monfluorothrin, transpermethrin, profluthrin Protrifenbut, ⁇ -tefluthrin, terraretrin, tetramethylfluthrin; bioetanomethrin.
  • DDTs Sodium channel modulators
  • Nicotinic acetylcholine receptor agonist Competitive modulator :: Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nitenpyram, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyraziflon, triflumesopirim. Dichloromethane, flupyrimin.
  • Nicotinic acetylcholine receptor (nAChR) allosteric modulator spinetram, spinosad.
  • Allosteric modulators abamectin, emamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, dramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadecin.
  • Juvenile hormone analogs hydroprene, quinoprene, methoprene, phenoxycarb, pyriproxyfen; diophenolan, epophenonan, triprene.
  • Non-specific (multisite) inhibitors methyl bromide, alkyl halides; chloropicrin, sodium aluminum fluoride, sulfuryl fluoride; borax, liquor stone; disodium octaborate salt, boric acid Sodium salt, sodium metaborate salt; Dazomet, metam, metam potassium salt, metam sodium salt.
  • String organ TRPV channel modulator Pymetrodin, pyrifluquinazone; Afidopyropen.
  • Tick growth inhibitors clofentezine, difluorovidazine, hexitiazox, etoxazole.
  • Microbial-derived insect midgut endometrial disrupting agents Bt subsp. Israelensis, Bt subsp. Aizawai, Bt subsp. Kurstaki, Bt subsp. Tenebrionis; Proteins contained in Bt crops: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1; Bacillus sphaericus.
  • Mitochondrial ATP synthase inhibitor diafentiurone; azocyclotin, cyhexatin, fenbutatin oxide; propargite; tetradiphon.
  • Oxidative phosphorylation decoupling agent that disturbs the proton gradient chlorfenapyr, sulfuramide, DNOC, binapacryl, dinobutone, dinocup.
  • Nicotinic Acetylcholine Receptor (nAChR) Channel Blocker Bensultap, Cartap Hydrochloride; Nelystoxin; Thiosultap Monosodium Salt, Thiocyclum.
  • Chitin biosynthesis inhibitor Type 0 bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflubenzuron, fluazuron.
  • Chitin biosynthesis inhibitor, type 1 buprofezin
  • Moulting inhibitor cyromazine.
  • Molting hormone (ecdysone) receptor agonists chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
  • Octopamine receptor agonists Amitraz, Chlordimeform.
  • Mitochondrial electron transport chain complex III inhibitor acequinosyl, fluacripirim, hydramethylnon; biphenazate.
  • Mitochondrial electron transport chain complex I inhibitor METI: phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, rotenone.
  • Asinonapill benzpyrimoxane, fromotkin, fullhexafone, oxadiazolefil, cyclamate pyrazoflor. Amidoflumet, disicranyl, phenoxacrim, fentrifanyl, flubenzimine, metoxadiazone, tetrasul, triarasen.
  • Anthelmintic (A) Benzimidazole system: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; fevantel, netobimin, thiophanate; thiabendazole, cambendazole; (B) Salicylanilide system: closantel, oxyclozanide, lafoxanide, niclosamide; (C) Substituted phenolic system: nitroxynyl, nitroscanate; (D) Pyrimidines: Pyrantel, Morantel; (E) Imidazothiazole type: levamisole, tetramisole; (F) Tetrahydropyrimidines: Praziquantel, Epsiprantel; (G) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole,
  • the agricultural and horticultural fungicide of the present invention is not particularly limited depending on the dosage form.
  • dosage forms such as wettable powders, emulsions, powders, granules, aqueous solvents, suspensions, granule wettable powders, and tablets can be mentioned.
  • the preparation method for the preparation is not particularly limited, and a known preparation method can be adopted depending on the dosage form.
  • (Formation example 1: wettable powder) 40 parts of the thienopyrimidine compound of the present invention, 53 parts of diatomaceous soil, 4 parts of higher alcohol sulfate ester and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder having 40% of the active ingredient.
  • (Formation example 6: Granule wettable powder) 40 parts of thienopyrimidine compound of the present invention, 36 parts of clay, 10 parts of potassium chloride, 1 part of sodium alkylbenzene sulfonic acid salt, 8 parts of sodium lignin sulfonic acid salt and 5 parts of formaldehyde condensate of sodium alkylbenzene sulfonic acid salt are uniformly mixed. After finely crushing, add an appropriate amount of water and knead to make it clay-like. The clay-like material is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.
  • the thienopyrimidine compound of the present invention can be used as a prophylactic or therapeutic agent for controlling harmful pathogens, particularly fungi, which infect humans or animals.
  • the medical / animal antifungal agent of the present invention contains at least one selected from the compound (I) and the compound represented by the compound (II) or a salt thereof as an active ingredient.
  • the amount of the compound (I) and the compound represented by the compound (II) or a salt thereof contained in the medical antifungal agent of the present invention is not particularly limited as long as it exhibits an antifungal effect.
  • animal refers to pet animals, livestock and poultry, exhibited animals bred in zoos and aquariums, captured wild animals, and vertebrates such as research and experimental animals (Ve r t e b). It means r a t a).
  • mice can be mentioned, but specific examples of animals are not limited to these. Lambs, goats, pigs, horses, cows, squirrels, donkeys, mules, camels, llamas, alpaca, wild boars, reindeer, deer, mink, elephants, bears, kangaroos, foxes, dogs, cats, squirrels, rabbits, mice, rats, Mammals such as guinea pigs, hamsters, monkeys and ferrets.
  • animals can be mentioned, but specific examples of animals are not limited to these. Lambs, goats, pigs, horses, cows, squirrels, donkeys, mules, camels, llamas, alpaca, wild boars, reindeer, deer, mink, elephants, bears, kangaroos, foxes, dogs, cats, squirrels, rabbits, mice, rats, Mammals such as guinea pigs, hamsters, monkeys and ferret
  • Birds such as pigeons, parakeets, parrots, Java sparrows, Bengalese finch, canaries, chickens, ducks, squirrels, ducks, whales, sparrows, ostriches, sparrows, sparrows, quails, 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, medaka, tropical fish, yellowtail, yellowtail, Thailand, amberjack, salmon, mackerel, sea bass, que, tuna, horse mackerel, horse mackerel, blowfish.
  • fungus as a pathogenic bacterium to which the medical / animal antifungal agent of the present invention can be applied is shown below.
  • the 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 flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, the genus Aspergillus parasiticus, the genus Aspergillus; Blumeria genus such as Blumeria graminis; Candida genus such as Candida albicans, Candida glabrata, Candida krusei, Candida parapsilosis, Candida tropicalis; Cladosporium genus Cladosporium cladosporoides, Cladosporium herbarium, etc.
  • the antifungal agent of the present invention is suitable for the genus Aspergillus, Trichophyton or Candida, and particularly suitable for Aspergillus fumigatus or Trichophyton tonsurans.
  • mycosis is shown below as an infectious disease to which the medical / animal antifungal agent of the present invention can be applied.
  • the specific examples are not limited to these.
  • the medical / animal antifungal agent of the present invention can be applied to any of systemic fungal infections, superficial fungal infections and the like.
  • fungal infections include pulmonary aspergillosis, aspergillus disease such as systemic aspergillosis (prone to develop in immunosuppressed patients such as bone marrow recipients or AIDS patients), and candida (systemic candidiosis).
  • Candida disease Cryptococcus meningitis, rhinocerebral mucomycosis, pulmonary mucor disease, blastomycosis, histoplasmosis, coccidiomycosis, paracoccidiomycosis, paracoccidiomycosis Corneal mycosis, sporotricum disease, chromoblastomicosis, chromomicosis, pheofihomycosis, zygomycosis, cryptococcidioidomycosis, disseminated sporotricum disease, ringworm, ringworm, ringworm, ringworm , Crotch tinea (ringworm), tinea pedis (waterworm), tinea pedis (ringworm), tinea pedis (ringworm), skin, mouth, or vaginal candidiasis, malacetia, chronic mucocutaneous tinea Be done.
  • the antifungal agent of the present invention can also be applied to allergic diseases caused by fungi, such as
  • the medical / animal antifungal agent of the present invention can contain pharmaceutically acceptable additives.
  • the additive is not particularly limited as long as it is used in a known medical drug. These are, of course, sterile and non-heat-generating.
  • the additive can be appropriately selected depending on the dosage form of the antifungal agent, the administration method, and the like.
  • the dosage form that the medical / animal antifungal agent of the present invention can take is not particularly limited, and for example, a solid agent such as a tablet, a powder, a granule, a granule, a capsule, a troche (candy), or a pellet; a syrup.
  • Liquid agents such as emulsions, suspensions, solutions, Pour-on agents, Spot-on agents, etc .; semi-solid preparations such as ointments, gels, etc .; aerosols, steam, etc. Gas agents; nanoparticle preparations and the like can be mentioned.
  • the medical antifungal agent of the present invention can be administered by a known method.
  • the administration method includes, for example, subcutaneous, intravenous, intramuscular, intrathoracic (intrasternally) injection (injection); insertion into the anus, vagina, etc., application to the skin surface, spraying, dripping, etc.
  • Oral administration such as oral administration; nasal administration such as inhalation.
  • the additives that can be used in the medical and animal antifungal agents of the present invention include solubilizers such as cyclodextrin or modified cyclodextrin; lactose, dextrose, saccharose, cellulose, corn starch or Diluting agents such as potato starch; lubricants such as silica, talc, stearic acid, magnesium stearate or calcium stearate, polyethylene glycol; binding of starch, arabic gums, gelatin, methyl cellulose, carboxymethyl cellulose or polyvinylpyrrolidone, etc.
  • solubilizers such as cyclodextrin or modified cyclodextrin
  • lactose dextrose, saccharose, cellulose, corn starch or Diluting agents
  • lubricants such as silica, talc, stearic acid, magnesium stearate or calcium stearate, polyethylene glycol
  • binding of starch arabic gums, gelatin, methyl
  • Agents disaggregating agents such as starch, alginic acid, alginate or sodium starch glycolate; effervescing mixtures; pigments; sweeteners; wetting agents such as lecithin, polysorbate, laurylsulphates; Alternatively, non-toxic and pharmacologically inactive substances generally used in pharmaceutical preparations can be mentioned.
  • additives can be contained in the medical antifungal agent of the present invention by a known method such as mixing, granulation, tableting, sugar coating, or film coating.
  • a solubilizing agent such as cyclodextrin or modified cyclodextrin, saccharose, glycerin, mannitol, sorbitol, natural Gum, agar, sodium alginate, pectin, methyl cellulose, carboxymethyl cellulose, polyvinyl alcohol and the like can be mentioned.
  • the additives that can be used in the medical and animal antifungal agents of the present invention include sterile water, olive oil, glycols such as ethyl oleate and propylene glycol, cyclodextrin, and modified cyclo. Examples thereof include solubilizing agents such as dextrin. Further, if necessary, an appropriate amount of lidocaine hydrochloride can be added.
  • examples of the additive that can be used for the medical / animal antifungal agent of the present invention include carriers such as sterile water; solubilizers such as cyclodextrin and modified cyclodextrin. it can. These can also be included in the form of a sterilized isotonic saline solution.
  • the amount of the compound (I) and the compound represented by the compound (II) or a salt thereof contained in the medical / animal antifungal agent of the present invention is preferably 85% by weight or less with respect to the weight of the antifungal agent. , More preferably 50% by weight or less.
  • the dose of the medical / animal antifungal agent of the present invention can be appropriately selected according to the administration method, the type of infected fungus, the age, weight, symptoms and the like of the patient. For example, for adults, in the case of oral or parenteral (injection, infusion, etc.) administration, it can be administered once or several times a day at a dose of 0.1 to 100 mg / kg-body weight.
  • the medical / animal antifungal agent of the present invention can be used in combination with an agent other than the compound represented by the compound (I) and the compound (II) or a salt thereof.
  • the solvent was distilled off under reduced pressure, and the obtained residue was washed with diethyl ether to obtain the target compound (11.34 g). Yield 86%
  • the obtained NMR data of the target product is as follows. 1 1 H-NMR (CDCl 3 ) ⁇ : 11.00 (1H, s), 5.94-5.85 (1H, m), 5.28 (1H, d), 5.19 (1H, dd), 5.03 (1H, s), 4.36 (2H) , q), 4.28 (2H, q), 3.97-3.94 (2H, m), 2.74 (3H, s), 1.42 (3H, t), 1.35 (3H, t).
  • Step 2 Ethyl 3-allyl-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate [ethyl 3-allyl-5-methyl-2, Synthesis of 4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate]
  • Step 3 Ethyl 3-allyl-1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3] -D] Pyrimidine-6-carboxylate [ethyl 3-allyl-1-(2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-1,2,3 , 4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate] synthesis
  • the reaction mixture was concentrated under reduced pressure, and the obtained residue was washed with chloroform to obtain the target compound (5.68 g). Yield 80%
  • the obtained NMR data of the target product is as follows. 1 1 H-NMR (DMSO-D 6 ) ⁇ : 7.63-7.53 (1H, m), 7.53-7.48 (1H, m), 7.37-7.31 (1H, m), 5.32 (2H, s), 4.23 (2H, q), 3.99 (3H, s), 2.75 (3H, s), 1.24 (3H, t).
  • Ethyl 1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine -6-carboxylate (530 mg) is dissolved in N, N-dimethylformamide (12.6 mL), tert-butyl N- (2-bromoethyl) carbamate (338 mg) and potassium carbonate (347 mg) are added, and 80 ° C. Was stirred for 4 hours.
  • a saturated aqueous ammonium chloride solution was added to the reaction solution, the mixture was extracted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the obtained residue was dissolved in a mixed solution of tetrahydrofuran (1.7 mL) and methanol (1.7 mL).
  • Sodium borohydride 22 mg was added under ice-cooling, and the mixture was stirred at room temperature for 30 minutes.
  • a saturated aqueous solution of ammonium chloride was added to the reaction solution, the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain the target compound (80 mg). Yield 41%
  • the obtained NMR data of the target product is as follows.
  • A-1 and A-2, A-3 and A-4, A-5 and A-6, A-29 and A-30, A-31 and A-32, A-33 and A-34, A-38 and A-39, A-40 and A-41, A-42 and A-44, A-43 and A-45, A-46 and A-47, A-48 and A-49, A- 50 and A-51, A-53 and A-54, A-56 and A-57, A-58 and A-59, and A-62 and A-63 are in a stereosexual relationship, respectively.
  • A-16 1 1 H-NMR (CDCl 3 , ⁇ ppm): 1.09-1.46 (m, 18H), 2.85 (s, 3H), 2.91-2.95 (m, 2H), 4.00-4.53 (m, 9H) , 5.18-5.36 (m, 2H), 6.99-7.62 (m, 3H).
  • Compound No. A-22 1 1 H-NMR (CDCl 3 , ⁇ ppm): 0.73-1.41 (m, 12H), 2.06-2.18 (m, 1H), 2.81-2.84 (m, 3H), 3.79-4.75 (m, 9H), 5.41-5.52 (m, 1H), 6.79-6.99 (m, 2H), 7.39-7.53 (m, 1H).
  • A-60 1 1 H-NMR (CDCl 3 , ⁇ ppm): 0.51-0.85 (m, 4H), 1.24-1.28 (m, 3H), 2.04-2.11 (m, 1H), 2.41-2.65 (m, 5H), 3.75-3.93 (m, 5H), 4.22-5.72 (m, 8H), 6.46 (s, 1H), 6.78-7.73 (m, 5H).
  • Compound No. 0.51-0.85 (m, 4H), 1.24-1.28 (m, 3H), 2.04-2.11 (m, 1H), 2.41-2.65 (m, 5H), 3.75-3.93 (m, 5H), 4.22-5.72 (m, 8H), 6.46 (s, 1H), 6.78-7.73 (m, 5H).
  • A-62 1 1 H-NMR (CDCl 3 , ⁇ ppm): 1.24-1.30 (m, 3H), 2.43 (s, 3H), 3.36 (s, 3H), 3.56-4.80 (m, 7H), 5.40 -5.43 (m, 1H), 6.48 (s, 1H), 6.64-7.73 (m, 5H).
  • Compound No. A-63 1 1 H-NMR (CDCl 3 , ⁇ ppm): 1.24-1.31 (m, 3H), 2.43 (s, 3H), 3.36 (s, 3H), 3.56-4.82 (m, 7H), 5.53 -5.59 (m, 1H), 6.46 (s, 1H), 6.64-7.72 (m, 5H).
  • A-65 1 1 H-NMR (CDCl 3 , ⁇ ppm): 0.51-0.89 (m, 4H), 1.24-1.28 (m, 4H), 2.39-2.47 (m, 3H), 3.88-4.75 (m, 5H), 5.64-5.82 (m, 1H), 6.47-7.76 (m, 6H).
  • Compound No. A-66 1 1 H-NMR (CDCl 3 , ⁇ ppm): 0.77 (t, 3H), 1.24-1.46 (m, 4H), 1.89-2.14 (m, 2H), 2.37-2.43 (m, 3H) , 3.86-4.75 (m, 5H), 5.42-5.69 (m, 1H), 6.45-7.73 (m, 6H).
  • A-80 1 1 H-NMR (CDCl 3 , ⁇ ppm): 1.05-1.26 (m, 15H), 2.20-2.30 (m, 1H), 2.58-2.66 (m, 1H), 2.68 (s, 3H) , 3.89 (s, 3H), 3.96-4.45 (m, 3H), 6.86-7.11 (m, 4H), 7.80 (s, 2H).
  • the control price was calculated by the following formula.
  • Control value (%) 100- ⁇ Ratio of lesion area in treated plot / Ratio of lesion area in untreated plot ⁇ ⁇ 100
  • the apple scab control test was conducted on the thienopyrimidine compounds shown in Table 5. Both compounds showed a control value of 75% or more.
  • a cucumber Botrytis cinerea control test was conducted on the thienopyrimidine compounds shown in Table 6. Both compounds showed a control value of 75% or more.
  • Test Example 4 Wheat Red Rust Control Test Water was added to the emulsion (I) so that the concentration of the thienopyrimidine compound was 125 ppm, and the mixture was dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on wheat seedlings (cultivar "Norin 61", 1st and 2nd leaf stages) cultivated in a seedling raising pot. After air-drying, the wheat seedlings sprayed with the chemical solution were inoculated by sprinkling summer spores of wheat leaf rust (Puccinia recondita) (treatment plot).
  • wheat seedlings not sprayed with the drug solution were inoculated in the same manner as above (untreated plot). They were allowed to stand in a greenhouse at 20 ° C. On the day 12 days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.
  • Wheat powdery mildew seed treatment test Emulsion (I) was applied to wheat seeds (variety "Chihoku") so that (weight of thienopyrimidine compound) / (weight of seeds) was 100 g / 100 kg. Seed processed. These seeds were sown in pots, and 8 to 10 days later, they were inoculated by sprinkling conidia of wheat powdery mildew (Erysiphe granis f.sp.tritici) (treatment plot). As a control, untreated wheat seedlings were inoculated in the same manner as above (untreated plot). They were allowed to stand in a greenhouse at 20 ° C. On the day 7 days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.
  • Wheat powdery mildew soil irrigation test Concentration of thienopyrimidine compound by adding water to emulsion (I) to a pot (5.5 cm x 5.5 cm) in which wheat seeds (variety "Chihoku") were sown. 10 mL of a drug solution having a concentration of 100 ppm was irrigated, and 8 to 10 days later, conidia of wheat powdery mildew (Erysiphy powdery mildew) were sprinkled and inoculated (treatment group). As a control, untreated wheat seedlings were inoculated in the same manner as above (untreated plot). They were allowed to stand in a greenhouse at 20 ° C. On the day 7 days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.
  • the wheat powdery mildew soil irrigation treatment test was conducted on the thienopyrimidine compounds shown in Table 10. Both compounds showed a control value of 75% or more.
  • Test examples show that the thienopyrimidine compound of the present invention is useful as an active ingredient of an antifungal agent for medical use and animals.
  • Test Example 7 Antibacterial test against Fusarium graminearm Water was added to the emulsion (I) so that the concentration of the thienopyrimidine compound was 125 ppm, and the mixture was dissolved to obtain a drug solution. Spores of Fusarium graminearm were added and dispersed in a potato sucrose yeast extract medium, and the above drug solution was further added and mixed so that the concentration of the thienopyrimidine compound in the culture medium was 15.6 ppm, and these were added and mixed in 96 holes.
  • the thienopyrimidine compounds shown in Table 11 were subjected to an antibacterial test against Fusarium graninearum. Both compounds showed an excellent growth inhibition rate of 50% or more.
  • Test Example 8 Antibacterial test against Aspergillus niger Spores of Aspergillus niger were added and dispersed in Vogel medium, and a thienopyrimidine compound dissolved in dimethyl sulfoxide was added and mixed so as to be 25 ppm, and these were added and mixed on a 96-well microplate.
  • the thienopyrimidine compounds shown in Table 12 were subjected to an antibacterial test against Aspergillus niger. Both compounds showed an excellent growth inhibition rate of 50% or more.
  • the thienopyrimidine compounds of the present invention have a bactericidal effect, including compounds that could not be exemplified. It is a compound that does not cause phytotoxicity to plants and has little toxicity to humans, livestock and fish and has little impact on the environment, and is useful as a pesticide and an antifungal agent for medical and animal use.

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Abstract

Le but de la présente invention est de fournir un composé 2,4-dioxo-1,4-dihydrothiénopyrimidine qui présente une excellente activité bactéricide et une excellente innocuité et qui peut être synthétisé de manière avantageuse sur le plan industriel, et un agent fongicide agricole ou horticole, ou un agent antifongique médical/animal le contenant en tant que composant actif.　Le composé 2,4-dioxo-1,4-dihydrothiénopyrimidine selon l'invention est un composé représenté par la formule (I) ou un sel de celui-ci.　Dans la formule (I), X1 représente un groupe halogène, un groupe alkyle en C1-6 substitué ou non substitué, etc, X2 représente un groupe halogène, un groupe alkyle en C1-6 substitué ou non substitué, etc, et X3, X4, X5 et X6 représentent indépendamment un atome d'hydrogène ou un groupe alkyle en C1-6 substitué ou non substitué. Q est un groupe représenté par la formule (Q-1), etc, A représente un groupe alkylène en C1-6 substitué ou non substitué, un groupe alcénylène en C2-6 substitué ou non substitué, etc, et Y représente un groupe aryle en C6-10 substitué ou non substitué.
PCT/JP2020/045190 2019-12-05 2020-12-04 Composé 2,4-dioxo-1,4-dihydrothiénopyrimidine, agent fongicide agricole ou horticole, ou agent antifongique médical/animal le contenant WO2021112213A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008143262A1 (fr) * 2007-05-21 2008-11-27 Takeda Pharmaceutical Company Limited Composé hétérocyclique et son utilisation
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
JP2016520064A (ja) * 2013-05-10 2016-07-11 ニンバス アポロ，インコーポレーテッド Ａｃｃ阻害剤及びその使用
JP2018538246A (ja) * 2015-10-26 2018-12-27 ギリアド アポロ， エルエルシー Ａｃｃ阻害剤およびその使用
WO2019020041A1 (fr) * 2017-07-26 2019-01-31 南京圣和药业股份有限公司 Composé utilisé en tant qu'inhibiteur d'acc et utilisation associée

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008143262A1 (fr) * 2007-05-21 2008-11-27 Takeda Pharmaceutical Company Limited Composé hétérocyclique et son utilisation
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
JP2016520064A (ja) * 2013-05-10 2016-07-11 ニンバス アポロ，インコーポレーテッド Ａｃｃ阻害剤及びその使用
JP2018538246A (ja) * 2015-10-26 2018-12-27 ギリアド アポロ， エルエルシー Ａｃｃ阻害剤およびその使用
WO2019020041A1 (fr) * 2017-07-26 2019-01-31 南京圣和药业股份有限公司 Composé utilisé en tant qu'inhibiteur d'acc et utilisation associée

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