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WO2021112213A1 - 2,4-dioxo-1,4-dihydrothienopyrimidine compound, agricultural or horticultural fungicidal agent, or medical/animal antifungal agent, containing this - Google Patents

2,4-dioxo-1,4-dihydrothienopyrimidine compound, agricultural or horticultural fungicidal agent, or medical/animal antifungal agent, containing this Download PDF

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Publication number
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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French (fr)
Japanese (ja)
Inventor
頼人 ▲桑▼原
岩田　淳
拓真 石原
斎賀　睦幸
貴昭 寺西
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Nippon Soda Co Ltd
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Nippon Soda Co Ltd
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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

The purpose of the present invention is to provide a 2,4-dioxo-1,4-dihydrothienopyrimidine compound that has excellent bactericidal activity and excellent safety and that can be industrially synthesized advantageously, and an agricultural or horticultural fungicidal agent, or medical/animal antifungal agent, containing this as an active component.　This 2,4-dioxo-1,4-dihydrothienopyrimidine compound is a compound represented in formula (I) or a salt thereof.　In formula (I), X1 represents a halogen group, a substituted or unsubstituted C1-6 alkyl group, etc., X2 represents a halogen group, a substituted or unsubstituted C1-6 alkyl group, etc., and X3, X4, X5 and X6 independently represent a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. Q is a group represented by formula (Q-1), etc.　A represents a substituted or unsubstituted C1-6 alkylene group, a substituted or unsubstituted C2-6 alkenylene group, etc., and Y represents a substituted or unsubstituted C6-10 aryl group.

Description

２，４－ジオキソ－１，４－ジヒドロチエノピリミジン化合物、及びそれを含有する農園芸用殺菌剤又は医療用・動物用抗真菌剤2,4-Dioxo-1,4-dihydrothienopyrimidine compound and agricultural and horticultural fungicides containing it or antifungal agents for medical and animal use

　本発明は、２，４－ジオキソ－１，４－ジヒドロチエノピリミジン化合物及びその用途に関する。より詳細に、本発明は、殺菌活性に優れ、安全性に優れ、且つ工業的に有利に合成できる２，４－ジオキソ－１，４－ジヒドロチエノピリミジン化合物、及びこれを有効成分として含有する農園芸用殺菌剤又は医療用・動物用抗真菌剤に関する。
　本願は、２０１９年１２月５日に出願された日本国特許出願第２０１９－２２０５８２号に対し優先権を主張し、その内容をここに援用する。 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.

　農園芸作物の栽培に当り、作物の病害に対して防除活性を有する化合物が種々提案されている。そのような化合物を農園芸用殺菌剤として実用するためには、効力が十分に高いだけでなく、薬剤抵抗性が生じ難いこと、植物に対する薬害や土壌汚染を生じさせないこと、家畜や魚類などに対する毒性が低いことなどが要求される。 In cultivating agricultural and horticultural crops, various compounds having control activity against diseases of crops have been proposed. In order to put such a compound into practical use as a fungicide for agriculture and horticulture, it is not only highly effective, it is unlikely to cause drug resistance, it does not cause phytotoxicity or soil contamination to plants, and it is resistant to livestock and fish. It is required to have low toxicity.

　ところで、特許文献１には、式（Ａ）で表される化合物などが開示されている。

Figure JPOXMLDOC01-appb-C000006
By the way, Patent Document 1 discloses a compound represented by the formula (A) and the like.
Figure JPOXMLDOC01-appb-C000006

　特許文献２には、式（Ｂ）で表される化合物などが開示されている。

Figure JPOXMLDOC01-appb-C000007
Patent Document 2 discloses a compound represented by the formula (B) and the like.
Figure JPOXMLDOC01-appb-C000007

　特許文献３には、式（Ｃ）で表される化合物などが開示されている。

Figure JPOXMLDOC01-appb-C000008
Patent Document 3 discloses a compound represented by the formula (C) and the like.
Figure JPOXMLDOC01-appb-C000008

　特許文献４には、式（Ｄ）で表される化合物などが開示されている。

Figure JPOXMLDOC01-appb-C000009
Patent Document 4 discloses a compound represented by the formula (D) and the like.
Figure JPOXMLDOC01-appb-C000009

　特許文献５には、式（Ｅ）で表される化合物などが開示されている。

Figure JPOXMLDOC01-appb-C000010
Patent Document 5 discloses a compound represented by the formula (E) and the like.
Figure JPOXMLDOC01-appb-C000010

　特許文献６には、式（Ｆ）で表される化合物などが開示されている。また、特許文献７には、式（Ｆ）で表される化合物などの農園芸用殺菌剤用途が開示されている。

Figure JPOXMLDOC01-appb-C000011
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).
Figure JPOXMLDOC01-appb-C000011

特許文献８には、式(Ｇ)で表される化合物などが開示されている。

Figure JPOXMLDOC01-appb-C000012
Patent Document 8 discloses a compound represented by the formula (G) and the like.
Figure JPOXMLDOC01-appb-C000012

特許文献９には、式(Ｈ)で表される化合物などが開示されている。

Figure JPOXMLDOC01-appb-C000013
Patent Document 9 discloses a compound represented by the formula (H) and the like.
Figure JPOXMLDOC01-appb-C000013

ＷＯ　２０１３／０７１１６９　ＡWO 2013/071169 A ＷＯ　２０１５／００７４５１　ＡWO 2015/007451 A ＷＯ　２０１７／０７５０５６　ＡWO 2017/075056 A ＷＯ　２０１７／０９１６００　ＡWO 2017/091600 A ＷＯ　２０１７／０９１６０２　ＡWO 2017/091602 A ＷＯ　２０１７／０９１６１７　ＡWO 2017/091617 A ＷＯ　２０１７／０９１６２７　ＡWO 2017/091627 A ＷＯ　２０１８／１７１６９８　ＡWO 2018/171698 A ＷＯ　２０１８／１７１６９９　ＡWO 2018/171699 A

　本発明の課題は、殺菌活性に優れ、安全性に優れ、且つ工業的に有利に合成できる２，４－ジオキソ－１，４－ジヒドロチエノピリミジン化合物（以下、単に「チエノピリミジン化合物」ということがある。）、及びこれを有効成分として含有する農園芸用殺菌剤又は医療用・動物用抗真菌剤を提供することである。 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.

　本発明者らは、上記課題を解決すべく鋭意検討した結果、以下の形態を包含する本発明を完成するに至った。
　すなわち、本発明は、以下の事項により特定される次のとおりのものである。
（１）
　式（Ｉ）で表される化合物又はその塩。

Figure JPOXMLDOC01-appb-C000014
〔式（Ｉ）中、
Ｘ1は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基、又はＲ１Ｏ－Ｎ＝ＣＲ６－で表される基を示し；
　Ｒ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ２は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ３は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ４は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよく、
　Ｒ５は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒ６は、水素原子、アミノ基、又は置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｘ２は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、又はＲ３Ｒ４Ｎ－ＳＯ２－で表される基を示し；
　Ｒ１～Ｒ５は、Ｘ１におけるそれらと同様の意味を示す。
　Ｘ３ 、Ｘ４ 、Ｘ５ 及びＸ６は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基を示し；
　Ｘ３ とＸ４は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｘ４ とＸ５は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｘ５ とＸ６  は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｑは、式（Ｑ－１）又は式（Ｑ－２）で表される基である。
Figure JPOXMLDOC01-appb-C000015
 　（式（Ｑ－１）及び式（Ｑ－２）中、矢印は結合部位を示し、
　Ｒcは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、Ｃ１～６アルキルアミノ基又は置換若しくは無置換のＣ３～６シクロアルキル基であり、Ｒｄ は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ１～６アルキルカルボニル基である。）
　Ａは、置換若しくは無置換のＣ１～６アルキレン基、置換若しくは無置換のＣ２～６アルケニレン基、置換若しくは無置換のＣ２～６アルキニレン基、又は置換若しくは無置換のＣ３～６シクロアルキレン基を示し；
　Ｙは、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～１０員環のヘテロシクリル基を示す。〕
（２）ＡにおけるＣ１～６アルキレン基又はＣ２～６アルケニレン基上の置換基が、
　ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、メルカプト基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の３～６員環のヘテロシクリル基、置換若しくは無置換の３～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒａ１－ＣＯ－で表される基、カルボキシ基、Ｒｂ１－Ｏ－ＣＯ－で表される基、Ｒｃ１Ｒｄ１Ｎ－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－で表される基、Ｒａ１－ＣＯ－Ｏ－で表される基、Ｒａ１－ＣＯ－ＮＲｅ１－で表される基、Ｒｂ１－Ｏ－ＣＯ－Ｏ－で表される基、Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－Ｏ－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－ＮＲｅ１－で表される基、Ｒｂ１ＳＯ２－ＮＲｅ１－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＳＯ２－で表される基、Ｒａ１Ｏ－Ｎ＝ＣＲｆ１－で表される基、Ｒｇ１Ｒｈ１Ｃ＝Ｎ－Ｏ－で表される基、オキソ基（Ｏ＝）、チオキソ基（Ｓ＝）、Ｒａ１－Ｎ＝で表される二価の基、Ｒａ１Ｏ－Ｎ＝で表される二価の基、Ｒｃ１Ｒｄ１Ｎ－Ｎ＝で表される二価の基、Ｒａ１－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基、Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基、Ｒｂ１ＳＯ２－ＮＲｅ１－Ｎ＝で表される二価の基からなる群より選択される１又は２以上の置換基であって；
　Ｒａ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｂ１は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｃ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｄ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、ここで、Ｒｃ１とＲｄ１は、一緒になって二価の有機基を形成してもよく、
　Ｒｅ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒｆ１は、水素原子、又は置換若しくは無置換のＣ１～６アルキル基を示し、
　Ｒｇ１は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｈ１は、水素原子、又は置換若しくは無置換のＣ１～６アルキル基を示し、ここで、Ｒｇ１とＲｈ１は、一緒になって二価の有機基を形成してもよく； 
　Ｃ１～６アルキレン基又はＣ２～６アルケニレン基上の置換基は２以上ある場合、そのうちの２つが一緒になって二価の有機基を形成してもよいものである；
（１）に記載の化合物又はその塩。
（３）式（Ｉ）が式（II）で表される、（１）又は（２）に記載の化合物又はその塩。
Figure JPOXMLDOC01-appb-C000016
 ［式（II）中、
　Ｘ１’は、置換若しくは無置換のＣ１～６アルコキシカルボニル基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換の５～６員ヘテロアリール基、シアノ基又は式「－ＣＲa’ ＝Ｎ－ＯＲb ’」で表される基である。
　Ｒa’ は、水素原子又はアミノ基であり、Ｒb’ は、水素原子又は置換又は無置換のＣ１～６アルキル基である。
　Ｘ２’は、置換又は無置換のＣ１～６アルキル基である。
　Ｘ３ 、Ｘ４ 、Ｘ５ 及びＸ６は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基である。
　Ｘ３ とＸ４ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｘ４ とＸ５ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｘ５ とＸ６ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｘ７ は、水酸基、置換若しくは無置換のＣ１～６アルコキシ基又は置換若しくは無置換のＣ１～６アルキルカルボニルオキシ基である。
　Ｘ８ は、水素原子である。
　Ｘ７ とＸ８ は、それらが一緒になって、オキソ基、又は置換若しくは無置換のＣ１～６アルコキシイミノ基を形成してもよい。
　Ｘ９ 及びＸ１０ は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基である。
　Ｘ８とＸ１０ は、それらが一緒になって、単結合を形成してもよい。
　Ｘ１１は、ハロゲノ基又は置換若しくは無置換のＣ１～６アルコキシ基である。
　ｎは、０～５のいずれかの整数であり、ｎが２以上のときＸ11は互いに同じでも異なってもよい。
　Ｑは、式（Ｑ－１）又は式（Ｑ－２）で表される基である。
Figure JPOXMLDOC01-appb-C000017
 　（式（Ｑ－１）及び式（Ｑ－２）中、矢印は結合部位を示し、
　Ｒcは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、Ｃ１～６アルキルアミノ基又は置換若しくは無置換のＣ３～６シクロアルキル基である。Ｒｄ は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ１～６アルキルカルボニル基である。）］
（４）（１）～（３）のいずれかに記載の化合物及びその塩からなる群から選ばれる、少なくとも１つを有効成分として含有する農園芸用殺菌剤。
（５）種子処理用である、（４）に記載の農園芸用殺菌剤。
（６）（１）～（３）のいずれかに記載の化合物、及びそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する医療用・動物用抗真菌剤。
（７）式（IV）で表される化合物又はその塩。
Figure JPOXMLDOC01-appb-C000018
 〔式（IV）中、
　Ｘ１は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基、又はＲ１Ｏ－Ｎ＝ＣＲ６－で表される基を示し；
　Ｒ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ２は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ３は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ４は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよく、
　Ｒ５は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒ６は、水素原子、アミノ基、又は置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｘ２は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、又はＲ３Ｒ４Ｎ－ＳＯ２－で表される基を示し；
　Ｒ１～Ｒ５は、Ｘ１におけるそれらと同様の意味を示す。
　Ｘ3 、Ｘ4 、Ｘ5 及びＸ6 は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基を示し；
　Ｘ３ とＸ４ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｘ４ とＸ５ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｘ５ とＸ６ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｑ’は、ＮＨ２又は ＣＨ２ＮＨ２で表される基を示す。　
　Ａは、置換若しくは無置換のＣ１～６アルキレン基、置換若しくは無置換のＣ２～６アルケニレン基、置換若しくは無置換のＣ２～６アルキニレン基、又は置換若しくは無置換のＣ３～６シクロアルキレン基を示し；
　Ｙは、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～１０員環のヘテロシクリル基を示す。〕 As a result of diligent studies to solve the above problems, the present inventors have completed the present invention including the following forms.
That is, the present invention is as follows specified by the following matters.
(1)
A compound represented by the formula (I) or a salt thereof.
Figure JPOXMLDOC01-appb-C000014
 [In formula (I),
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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl group ring, a substituted or unsubstituted 5-6 membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO A group represented by-, a group represented by R 3 R 4 N-, a group represented by R 3 R 4 N-CO-, a group represented by R 1 -CO-O-, a group represented by R 1- CO. -NR 5 - group represented by, R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O Group represented by-, group represented by R 3 R 4 N-CO-NR 5- , group represented by R 2 SO 2- NR 5- , represented by R 3 R 4 N-SO 2- Or a group represented by 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. 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 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.
Here, 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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO-, a group represented by, R 3 R 4 Group represented by N-, group represented by R 3 R 4 N-CO-, group represented by R 1- CO-O-, group represented by R 1- CO-NR 5- , R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O- , a group represented by, R 3 R 4 Indicates a group represented by N-CO-NR 5- , a group represented by R 2 SO 2- NR 5- , or a group represented by R 3 R 4 N-SO 2-;
R 1 to R 5 have the same meanings as those in X 1.
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).
Figure JPOXMLDOC01-appb-C000015
 (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. ]
(2) 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. Alternatively, 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. Substituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3 to 6-membered heterocyclyl group ring, a substituted or unsubstituted 3-6 membered heterocyclyloxy group ring, nitro group, cyano group, a group represented by R a1 -CO-, carboxy group, R b1 -O-CO- a group represented by, R c1 R d1 N- group represented by, R c1 R d1 N-CO-, a group represented by, R a1 -CO-O-, a group represented by, R a1 -CO- Group represented by NR e1- , group represented by R b1- O-CO-O-, group represented by R b1- O-CO-NR e1- , R c1 R d1 N-CO-O- The group represented by R c1 R d1 N-CO-NR e1- , the group represented by R b1 SO 2- NR e1- , and the group represented by R c1 R d1 N-SO 2-. Group, group represented by R a1 ON = CR f1- , group represented by R g1 R h1 C = NO-, oxo group (O =), thioxo group (S =), R a1- A divalent group represented by N =, a divalent group represented by R a1 ON =, a divalent group represented by R c1 R d1 NN =, R a1- CO-NR e1 A divalent group represented by -N =, a divalent group represented by R b1- O-CO-NR e1- N =, a divalent group represented by R b1 SO 2- NR e1- N = One or more substituents selected from the group consisting of groups;
Ra1 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 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. Alternatively, 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;
The compound according to (1) or a salt thereof.
(3) The compound according to (1) or (2) or a salt thereof, wherein formula (I) is represented by formula (II).
Figure JPOXMLDOC01-appb-C000016
 [In equation (II),
X 1 'are members independently selected from substituted or unsubstituted C1 ~ 6 alkoxycarbonyl group, a substituted or unsubstituted C1 ~ 6 alkyl group, a substituted or unsubstituted 5-6 membered heteroaryl group, a cyano group, or the formula "-CR a' = N-OR b' "is a group.
R a'is a hydrogen atom or amino group, and 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).
Figure JPOXMLDOC01-appb-C000017
 (In equations (Q-1) and (Q-2), the arrows indicate the binding sites.
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. )]
(4) An agricultural and horticultural fungicide containing at least one as an active ingredient, selected from the group consisting of the compound according to any one of (1) to (3) and a salt thereof.
(5) The fungicide for agriculture and horticulture according to (4), which is used for seed treatment.
(6) A medical / animal antifungal agent containing at least one selected from the group consisting of the compound according to any one of (1) to (3) and salts thereof as an active ingredient.
(7) A compound represented by the formula (IV) or a salt thereof.
Figure JPOXMLDOC01-appb-C000018
 [In equation (IV),
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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl group ring, a substituted or unsubstituted 5-6 membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO A group represented by-, a group represented by R 3 R 4 N-, a group represented by R 3 R 4 N-CO-, a group represented by R 1 -CO-O-, a group represented by R 1- CO. -NR 5 - group represented by, R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O Group represented by-, group represented by R 3 R 4 N-CO-NR 5- , group represented by R 2 SO 2- NR 5- , represented by R 3 R 4 N-SO 2- Or a group represented by 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. 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 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.
Here, 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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO-, a group represented by, R 3 R 4 Group represented by N-, group represented by R 3 R 4 N-CO-, group represented by R 1- CO-O-, group represented by R 1- CO-NR 5- , R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O- , a group represented by, R 3 R 4 Indicates a group represented by N-CO-NR 5- , a group represented by R 2 SO 2- NR 5- , or a group represented by R 3 R 4 N-SO 2-;
R 1 to R 5 have the same meanings as those in X 1.
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. ]

　本発明のチエノピリミジン化合物は、殺菌活性に優れ、効果が確実で、安全性に優れ、且つ工業的に有利に合成できる。
　本発明のチエノピリミジン化合物を含有する農園芸用殺菌剤は、優れた防除効果を有し、植物体に薬害を生じることがなく、人畜魚類に対する毒性や環境への影響が少ない。また、本発明のチエノピリミジン化合物は、医療用・動物用抗真菌剤としても有用である。 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.

〔チエノピリミジン化合物〕
　本発明のチエノピリミジン化合物は、式（Ｉ）で表される化合物（以下、化合物（Ｉ）と表記することがある。）、又は化合物（Ｉ）の塩である。 [Thienopyrimidine compound]
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).

Figure JPOXMLDOC01-appb-C000019
より好ましくは、式（II）で表される化合物（以下、化合物（II）と表記することがある。）、又は化合物（II）の塩である。
Figure JPOXMLDOC01-appb-C000019
 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).

Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020

　本発明において、用語「無置換（unsubstituted）」は、母核となる基のみであることを意味する。母核となる基の名称のみで記載しているときは、別段の断りがない限り「無置換」の意味である。
　一方、用語「置換(substituted)」は、母核となる基のいずれかの水素原子が、母核と同一又は異なる構造の基で置換されていることを意味する。従って、「置換基」は、母核となる基に結合した他の基である。置換基は１個であってもよいし、２個以上であってもよい。２個以上の置換基は同一であってもよいし、異なるものであってもよい。 In the present invention, the term "unsubstituted" means that there are only parental groups. When only the name of the parent group is described, it means "unsubstituted" unless otherwise specified.
On the other hand, 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.

　「置換基」は化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。
　「置換基」となり得る基の具体例としては、以下の基を挙げることができる。
　フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；
　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；
　ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などのＣ２～６アルケニル基； The "substituent" is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
Specific examples of 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;

　エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などのＣ２～６アルキニル基；
　シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；
　２－シクロプロペニル基、２－シクロペンテニル基、３－シクロヘキセニル基などのＣ３～６シクロアルケニル基；
　フェニル基、ナフチル基などのＣ６～１０アリール基；
　ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；
　ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；
　インドリル基、ベンゾフリル基、ベンゾチエニル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾチアゾリル基、キノリル基、イソキノリル基、キノキサリニル基などの縮合環のヘテロアリール基；
　オキシラニル基、テトラヒドロフリル基、ジオキソラニル基、ジオキサニル基などの環状エーテル基；
　アジリジニル基、ピロリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基などの環状アミノ基； 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 pyrimidinyl group, a pyridadinyl group, and a triazinyl group;
Heteroaryl group of fused ring such as indrill group, benzofuryl group, benzothienyl group, benzoimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group;
Cyclic ether groups such as oxylanyl group, tetrahydrofuryl group, dioxolanyl group, dioxanyl group;
Cyclic amino groups such as aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group;

　水酸基；
　オキソ基；
　メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；
　ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などのＣ２～６アルケニルオキシ基；
　エチニルオキシ基、プロパルギルオキシ基などのＣ２～６アルキニルオキシ基；
　フェノキシ基、ナフトキシ基などのＣ６～１０アリールオキシ基；
　チアゾリルオキシ基、ピリジルオキシ基などの５～６員環のヘテロアリールオキシ基； Hydroxy group;
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;

　カルボキシル基：カルボキシ基；
　ホルミル基；
　アセチル基、プロピオニル基などのＣ１～６アルキルカルボニル基；
　ホルミルオキシ基；
　アセチルオキシ基、プロピオニルオキシ基などのＣ１～６アルキルカルボニルオキシ基；
　メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などのＣ１～６アルコキシカルボニル基； 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;

　クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基、パーフルオロ－ｎ－ペンチル基などのＣ１～６ハロアルキル基；
　２－クロロ－１－プロペニル基、２－フルオロ－１－ブテニル基などのＣ２～６ハロアルケニル基；
　４，４－ジクロロ－１－ブチニル基、４－フルオロ－１－ペンチニル基、５－ブロモ－２－ペンチニル基などのＣ２～６ハロアルキニル基；
３，３－ジフルオロシクロブチル基などのＣ３～６ハロシクロアルキル基；
　２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基、２，２，２－トリフルオロエトキシ基などのＣ１～６ハロアルコキシ基；
　２－クロロプロペニルオキシ基、３－ブロモブテニルオキシ基などのＣ２～６ハロアルケニルオキシ基；
　クロロアセチル基、トリフルオロアセチル基、トリクロロアセチル基などのＣ１～６ハロアルキルカルボニル基； C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group, 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 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl groups, trifluoroacetyl groups, trichloroacetyl groups;

　シアノ基；
　ニトロ基；
　アミノ基；
　メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのＣ１～６アルキルアミノ基；
　アニリノ基、ナフチルアミノ基などのＣ６～１０アリールアミノ基；
　ホルミルアミノ基；
　アセチルアミノ基、プロパノイルアミノ基、ブチリルアミノ基、ｉ－プロピルカルボニルアミノ基などのＣ１～６アルキルカルボニルアミノ基；
　メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、ｎ－プロポキシカルボニルアミノ基、ｉ－プロポキシカルボニルアミノ基などのＣ１～６アルコキシカルボニルアミノ基；
　Ｓ，Ｓ－ジメチルスルホキシイミノ基などのＣ１～６アルキルスルホキシイミノ基； 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;

　アミノカルボニル基；
　メチルアミノカルボニル基、ジメチルアミノカルボニル基、エチルアミノカルボニル基、ｉ－プロピルアミノカルボニル基、などのＣ１～６アルキルアミノカルボニル基；
　イミノメチル基、１－イミノエチル基、１－イミノ－ｎ－プロピル基などのイミノＣ１～６アルキル基；
　ヒドロキシイミノメチル基、１－（ヒドロキシイミノ）エチル基、１－（ヒドロキシイミノ）－ｎ－プロピル基などのヒドロキシイミノＣ１～６アルキル基；
　メトキシイミノメチル基、１－（メトキシイミノ）エチル基などのＣ１～６アルコキシイミノＣ１～６アルキル基； 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;

　メルカプト基；
　メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｉ－プロピルチオ基、ｎ－ブチルチオ基、ｉ－ブチルチオ基、ｓ－ブチルチオ基、ｔ－ブチルチオ基などのＣ１～６アルキルチオ基；
　トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基；
　ビニルチオ基、アリルチオ基などのＣ２～６アルケニルチオ基；
　エチニルチオ基、プロパルギルチオ基などのＣ２～６アルキニルチオ基；
　メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などのＣ１～６アルキルスルフィニル基；
　トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；
　アリルスルフィニル基などのＣ２～６アルケニルスルフィニル基；
　プロパルギルスルフィニル基などのＣ２～６アルキニルスルフィニル基；
　メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などのＣ１～６アルキルスルホニル基；
　トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；
　アリルスルホニル基などのＣ２～６アルケニルスルホニル基；
　プロパルギルスルホニル基などのＣ２～６アルキニルスルホニル基；
　アミノチオカルボニル基； Mercapto 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 trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group;
C2-6 alkenylsulfinyl groups such as allylsulfinyl groups;
C2-6 alkynylsulfinyl groups such as propargylsulfinyl groups;
C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, t-butylsulfonyl groups;
C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups, 2,2,2-trifluoroethylsulfonyl groups;
C2-6 alkenylsulfonyl groups such as allylsulfonyl groups;
C2-6 alkynylsulfonyl groups such as propargylsulfonyl groups;
Amino thiocarbonyl group;

　トリメチルシリル基、トリエチルシリル基、ｔ－ブチルジメチルシリル基などのトリＣ１～６アルキルシリル基；
　トリフェニルシリル基などのトリＣ６～１０アリールシリル基 Tri-C1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
Tri-C6-10 arylsilyl groups such as triphenylsilyl groups

　これらの「置換基」は、当該置換基中のいずれかの水素原子が、異なる構造の基で置換されていてもよい。 In these "substituents", any hydrogen atom in the substituent may be substituted with a group having a different structure.

　「Ｃ１～６」などの用語は、母核となる基の炭素原子数が１～６個などであることを表している。この炭素原子数には、置換基の中に在る炭素原子の数を含まない。例えば、エトキシブチル基は、母核となる基がブチル基であり、置換基がエトキシ基であるので、Ｃ２アルコキシＣ４アルキル基に分類する。 Terms such as "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. For example, 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.

　〔Ｘ１〕
　Ｘ１は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、
Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、
Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、
Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基、又はＲ１Ｏ－Ｎ＝ＣＲ６－で表される基を示す。 [X 1 ]
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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl group ring, a substituted or unsubstituted 5-6 membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO A group represented by-, a group represented by R 3 R 4 N-, a group represented by R 3 R 4 N-CO-, a group represented by R 1 -CO-O-, a group represented by R 1- CO. -NR 5 - group represented by, R 2 -O-CO-O-, a group represented by the
Group represented by R 2- O-CO-NR 5- , group represented by R 3 R 4 N-CO-O-,
Group represented by R 3 R 4 N-CO-NR 5- , group represented by R 2 SO 2- NR 5-
Indicates a group represented by R 3 R 4 N-SO 2- or a group represented by R 1 ON = CR 6-.

　Ｒ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ２は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ３は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ４は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示す。
　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよい。
　Ｒ５は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒ６は、水素原子、アミノ基又は置換若しくは無置換のＣ１～６アルキル基を示す。 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.
Here, 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.

　Ｘ１における「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。 Examples of the "halogeno group" in X 1 include a fluoro group, a chloro group, a bromo group, an iod group and the like.

　Ｘ１における「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。Ｘ１における「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。 The "C1 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.

　Ｘ１における「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などを挙げることができる。 The "C2-6 alkenyl group" in 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.

　Ｘ１における「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などを挙げることができる。 The "C2-6 alkynyl group" in 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. 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 Groups, 1,1-dimethyl-2-butynyl group and the like can be mentioned.

　Ｘ１における「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、ｉ－プロポキシ基、ｉ－ブトキシ基、ｓ－ブトキシ基、ｔ－ブトキシ基、ｉ－ヘキシルオキシ基などを挙げることができる。
　Ｘ１における「Ｃ２～６アルケニルオキシ基」としては、ビニルオキシ基、アリルオキシ基、１－プロペニルオキシ基、ブテニルオキシ基などを挙げることができる。
　Ｘ１における「Ｃ２～６アルキニルオキシ基」としては、エチニルオキシ基、プロパルギルオキシ基などを挙げることができる。 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.

　Ｘ１における「Ｃ１～６アルキルチオ基」としては、メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｎ－ブチルチオ基、ｎ－ペンチルチオ基、ｎ－ヘキシルチオ基、ｉ－プロピルチオ基などを挙げることができる。
　Ｘ１における「Ｃ１～６アルキルスルフィニル基」としては、メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などを挙げることができる。
　Ｘ１における「Ｃ１～６アルキルスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などを挙げることができる。 Examples of the "C1 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.

　Ｘ１における「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」、「Ｃ１～６アルコキシ基」、「Ｃ２～６アルケニルオキシ基」、「Ｃ２～６アルキニルオキシ基」、「Ｃ１～６アルキルチオ基」、「Ｃ１～６アルキルスルフィニル基」、又は「Ｃ１～６アルキルスルホニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；　４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基で置換されたＣ６～１０アリール基；又はシアノ基；が好ましい。 "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 As the substituent on the "group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group", a halogeno such as a fluoro group, a chloro group, a bromo group, or an iodo 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; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; phenyl group , C6-10aryl groups such as naphthyl groups; halogeno groups, C1-6 haloalkyl groups, or C1-6 haloalkoxy groups such as 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group. A C6-10 aryl group substituted with; or a cyano group; is preferred.

　Ｘ１における「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｘ１における「Ｃ３～６シクロアルキルオキシ基」としては、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基などを挙げることができる。 Examples of the "C3 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.

　Ｘ１における「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インダニル基、インデニル基、テトラリニル基、などを挙げることができる。
　Ｘ１における「Ｃ６～１０アリールオキシ基」としては、フェノキシ基、ナフトキシ基などを挙げることができる。 Examples of the "C6 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.

　Ｘ１における「Ｃ６～１０アリールチオ基」としては、フェニルチオ基、ナフチルチオ基などを挙げることができる。
　Ｘ１における「Ｃ６～１０アリールスルフィニル基」としては、フェニルスルフィニル基、ナフチルスルフィニル基などを挙げることができる。
　Ｘ１における「Ｃ６～１０アリールスルホニル基」としては、フェニルスルホニル基、ナフチルスルホニル基などを挙げることができる。 Examples of the "C6 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.

　Ｘ１における「５～６員環のヘテロシクリル基」とは、窒素原子、酸素原子及び硫黄原子からなる群から選ばれる１、２、３又は４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。「５～６員環のヘテロシクリル基」としては、５～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。 The "5- to 6-membered heterocyclyl group 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. 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. ..

　５～６員環の飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～６員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；などを挙げることができる。
　５～６員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；イソオキサゾリニル基、ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基；などが挙げられる。 Examples of the saturated heterocyclyl group having a 5- to 6-membered ring 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. And the like; 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.

　Ｘ１における「５～６員環のヘテロシクリルオキシ基」は、５～６員環のヘテロシクリル基とオキシ基が結合した構造を有する。具体例としては、チアゾリルオキシ基、ピリジルオキシ基などを挙げることができる。 "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.

　Ｘ１における「Ｃ３～６シクロアルキル基」、「Ｃ３～６シクロアルキルオキシ基」、「Ｃ６～１０アリール基」、「Ｃ６～１０アリールオキシ基」、「Ｃ６～１０アリールチオ基」、「Ｃ６～１０アリールスルフィニル基」、「Ｃ６～１０アリールスルホニル基」、「５～６員環のヘテロシクリル基」、又は「５～６員環のヘテロシクリルオキシ基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基で置換されたＣ６～１０アリール基；又はシアノ基；が好ましい。 "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-dichlorobutoxy group, trifluoromethoxy group; C6-10 aryl groups such as phenyl group, naphthyl group; 4-chlorophenyl group, 4-trifluoro A C6-10 aryl group; or a cyano group; substituted with a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group, such as a methylphenyl group, a 4-trifluoromethoxyphenyl group, is preferred.

　Ｘ１における「Ｒ１－ＣＯ－で表される基」中、Ｒ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示す。 In the "group represented by R 1- CO-" in X 1 , 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. C2 to 6 alkynyl groups, substituted or unsubstituted C3 to 6 cycloalkyl groups, substituted or unsubstituted C6 to 10 aryl groups, or substituted or unsubstituted 5- to 6-membered ring heterocyclyl groups.

　Ｒ１における「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。
　Ｒ１における「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基などを挙げることができる。
　Ｒ１における「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基などを挙げることができる。
　Ｒ１における「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、又は「Ｃ２～６アルキニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基で置換されたＣ６～１０アリール基；又はシアノ基；が好ましい。 As "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, cyclopentyl group, cyclohexyl group; phenyl group, naphthyl C6-10 aryl group such as group; substituted with halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group such as 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group. The C6-10 aryl group; or cyano group;

　Ｒ１における「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｒ１における「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インデニル基、インダニル基、テトラリニル基などを挙げることができる。 Examples of the "C3 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.

　Ｒ１における「５～６員環のヘテロシクリル基」とは、窒素原子、酸素原子及び硫黄原子からなる群から選ばれる１、２、３又は４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。「５～６員環のヘテロシクリル基」としては、５～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。
　５～６員環の飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。　
　５～６員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；などを挙げることができる。
　５～６員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；イソオキサゾリニル基、ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基；などが挙げられる。 In 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. 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 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. And the like; 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.

　Ｒ１における「Ｃ３～６シクロアルキル基」、「Ｃ６～１０アリール基」、又は「５～６員環のヘテロシクリル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基で置換されたＣ６～１０アリール基；又はシアノ基；が好ましい。 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 a C1-6 haloalkoxy group, such as a fluoromethoxyphenyl group, is preferred.

　「Ｒ１－ＣＯ－で表される基」の具体例としては、ホルミル基、アセチル基などを挙げることができる。 Specific examples of the "group represented by R 1 -CO-" may include formyl group, and acetyl group.

　Ｘ１における「Ｒ２－Ｏ－ＣＯ－で表される基」中、Ｒ２は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒ２における置換基の具体例は、Ｒ１において例示したものと同じものを挙げることができる。 During the "group represented by R 2 -O-CO-" in X 1, 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.

　「Ｒ２－Ｏ－ＣＯ－で表される基」の具体例としては、メトキシカルボニル基、エトキシカルボニル基などを挙げることができる。 Specific examples of the "group represented by R 2 -O-CO-" may include a methoxycarbonyl group and an ethoxycarbonyl group.

　Ｘ１における「Ｒ３Ｒ４Ｎ－で表される基」中、Ｒ３は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、Ｒ４は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒ３又はＲ４における置換基の具体例は、Ｒ１において例示したものと同じものを挙げることができる。 In the "group represented by R 3 R 4 N-" in X 1 , 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. 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 5-6-membered ring heterocyclyl group, R 4 Indicates 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 3 or R 4 can be the same as those exemplified in R 1.

　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよい。
　形成できる二価の有機基としては、置換若しくは無置換のＣ２～５アルキレン基又は置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ２～５アルキレン基」としては、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ２～５アルキレン基」又は「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；又はクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；が好ましい。 Here, R 3 and R 4 may 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.

　「Ｒ３Ｒ４Ｎ－で表される基」の具体例としては、アミノ基、メチルアミノ基、ジメチルアミノ基などを挙げることができる。 Specific examples of the "group represented by R 3 R 4 N-" include an amino group, a methyl amino group, a dimethyl amino group and the like.

　Ｘ１における「Ｒ３Ｒ４Ｎ－ＣＯ－で表される基」中、Ｒ３又はＲ４は上記の「Ｒ３Ｒ４Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ３Ｒ４Ｎ－ＣＯ－で表される基」の具体例としては、カルバモイル基、Ｎ，Ｎ－ジメチルアミノカルボニル基、Ｎ－（ｉ－プロピル）アミノカルボニル基、Ｎ－（ｉ－プロピル）－Ｎ－メチルアミノカルボニル基などを挙げることができる。 In the "group represented by R 3 R 4 N-CO-" in X 1 , 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.

　Ｘ１における「Ｒ１－ＣＯ－Ｏ－で表される基」中、Ｒ１は上記の「Ｒ１－ＣＯ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ１－ＣＯ－Ｏ－で表される基」の具体例としては、アセチルオキシ基などを挙げることができる。 Among the "groups represented by R 1- CO-O-" in X 1 , R 1 has the same meaning as those in the above " groups represented by R 1-CO-".
Specific examples of the "R 1 -CO-O-a group represented" can be mentioned an acetyl group.

　Ｘ１における「Ｒ１－ＣＯ－ＮＲ５－で表される基」中、Ｒ１は上記の「Ｒ１－ＣＯ－で表される基」におけるそれらと同様の意味を示す。
　Ｒ５は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒ５における置換基の具体例は、Ｒ１において例示したものと同じものを挙げることができる。
　「Ｒ１－ＣＯ－ＮＲ５－で表される基」の具体例としては、アセチルアミノ基などを挙げることができる。 Among the "groups represented by R 1- CO-NR 5- " in X 1 , 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.

　Ｘ１における「Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基」中、Ｒ２は上記の「Ｒ２－Ｏ－ＣＯ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基」の具体例としては、メトキシカルボニルオキシ基、エトキシカルボニルオキシ基などを挙げることができる。 During the "R 2 -O-CO-O- in group represented" in X 1, 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.

　Ｘ１における「Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基」中、Ｒ２は上記の「Ｒ２－Ｏ－ＣＯ－で表される基」におけるそれらと同様の意味を示す。Ｒ５は上記の「Ｒ１－ＣＯ－ＮＲ５－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基」の具体例としては、メトキシカルボニルアミノ基などを挙げることができる。 In X 1 - in "R 2 -O-CO-NR 5 group represented by", 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.

　Ｘ１における「Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基」中、Ｒ３又はＲ４は上記の「Ｒ３Ｒ４Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基」の具体例としては、カルバモイルオキシ基、Ｎ，Ｎ－ジメチルアミノカルボニルオキシ基などを挙げることができる。 In the " group represented by R 3 R 4 N-CO-O- " in X 1 , 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.

　Ｘ１における「Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基」中、Ｒ３又はＲ４は上記の「Ｒ３Ｒ４Ｎ－で表される基」におけるそれらと同様の意味を示す。Ｒ５は上記の「Ｒ１－ＣＯ－ＮＲ５－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基」の具体例としては、カルバモイルアミノ基、Ｎ，Ｎ－ジメチルアミノカルボニルアミノ基などを挙げることができる。 In the "group represented by R 3 R 4 N-CO-NR 5- " in X 1 , 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.

　Ｘ１における「Ｒ２ＳＯ２－ＮＲ５－で表される基」中、Ｒ２は上記の「Ｒ２－Ｏ－ＣＯ－で表される基」におけるそれらと同様の意味を示す。Ｒ５は上記の「Ｒ１－ＣＯ－ＮＲ５－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ２ＳＯ２－ＮＲ５－で表される基」の具体例としては、メタンスルホニルアミノ基などを挙げることができる。 Among the "groups represented by R 2 SO 2- NR 5- " in X 1 , R 2 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.

　Ｘ１における「Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基」中、Ｒ３又はＲ４は上記の「Ｒ３Ｒ４Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基」の具体例としては、Ｎ，Ｎ－ジメチルアミノスルホニル基などを挙げることができる。 In the "group represented by R 3 R 4 N-SO 2- " in X 1 , 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.

　Ｘ１における「Ｒ１Ｏ－Ｎ＝ＣＲ６－で表される基」中、Ｒ１は上記の「Ｒ１－ＣＯ－で表される基」におけるそれらと同様の意味を示す。
　Ｒ６は、水素原子、アミノ基又は置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｒ６における置換基の具体例は、Ｒ１において例示したものと同じものを挙げることができる。
　「Ｒ１Ｏ－Ｎ＝ＣＲ６－で表される基」の具体例としては、（ヒドロキシイミノ）メチル基、（エトキシイミノ）メチル基などを挙げることができる。 In X 1 - in "R 1 O-N = CR 6 group represented by", R 1 is the same meaning as described those in "group represented by R 1 -CO-" above.
R 6 represents a hydrogen atom, an amino group or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent in R 6 can be the same as those exemplified in R 1.
Specific examples of the "group represented by R 1 ON = CR 6- " include a (hydroxyimino) methyl group and a (ethoxyimino) methyl group.

　〔Ｘ２〕
　Ｘ２は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、又はＲ３Ｒ４Ｎ－ＳＯ２－で表される基を示す。
　また、Ｒ１～Ｒ５は、Ｘ１におけるそれらと同様の意味を示す。 [X 2 ]
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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO-, a group represented by, R 3 R 4 Group represented by N-, group represented by R 3 R 4 N-CO-, group represented by R 1- CO-O-, group represented by R 1- CO-NR 5- , R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O- , a group represented by, R 3 R 4 Indicates a group represented by N-CO-NR 5- , a group represented by R 2 SO 2- NR 5- , or a group represented by R 3 R 4 N-SO 2-.
Further, R 1 to R 5 have the same meanings as those in X 1.

　Ｘ２における置換基の具体例は、Ｘ１において例示したものと同じものを挙げることができる。 Specific examples of the substituent in X 2 can be the same as those exemplified in X 1.

　〔Ｘ３、Ｘ４、Ｘ５、Ｘ６〕
　式（I）中、Ｘ３ 、Ｘ４ 、Ｘ５ 及びＸ６ は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基である。
　Ｘ３ 、Ｘ４ 、Ｘ５ 及びＸ６ における「置換若しくは無置換のＣ１～６アルキル基」としては、Ｘ１において具体的に例示したそれらと同じものを挙げることができる。 [X 3 , X 4 , X 5 , X 6 ]
In formula (I), X 3 , X 4 , X 5 and 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.

　Ｘ３ とＸ４ は、それらが一緒になってＣ２～６アルキレン基を形成してもよい。
　Ｘ３ とＸ４ が、一緒になって形成する「Ｃ２～６アルキレン基」としては、エチレン基、トリメチレン基、テトラメチレン基、ペンタメチレン基などを挙げることができる。 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.

　Ｘ５ とＸ６ は、それらが一緒になってＣ２～６アルキレン基を形成してもよい。
　Ｘ５ とＸ６が、一緒になって形成する「Ｃ２～６アルキレン基」としては、前記したものと同様のものが挙げられる。 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.

Ｘ４ とＸ５ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｘ４ とＸ５が、一緒になって形成する「Ｃ２～６アルキレン基」としては、前記したものと同様のものが挙げられる。 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〕
　Ａは、置換若しくは無置換のＣ１～６アルキレン基、置換若しくは無置換のＣ２～６アルケニレン基、置換若しくは無置換のＣ２～６アルキニレン基、又は置換若しくは無置換のＣ３～６シクロアルキレン基を示す。 [A]
A represents a substituted or unsubstituted C1 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. ..

　Ａにおける「Ｃ１～６アルキレン基」としては、メチレン基、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　Ａにおける「Ｃ２～６アルケニレン基」としては、ビニレン基（－ＣＨ＝ＣＨ－）、ジビニレン基（－ＣＨ＝ＣＨ－ＣＨ＝ＣＨ－）、プロペニレン基（－ＣＨ＝ＣＨ－ＣＨ２－、－ＣＨ２－ＣＨ＝ＣＨ－）などを挙げることができる。
　Ａにおける「Ｃ２～６アルキニレン基」としては、エチニレン基（－Ｃ≡Ｃ－）、プロピニレン基（－ＣＨ２－Ｃ≡Ｃ－、－Ｃ≡Ｃ－ＣＨ２－）、などを挙げることができる。
　Ａにおける「Ｃ３～６シクロアルキレン基」としては、１，２－シクロプロピレン基、１，２－シクロブタンジイル基、１，３－シクロブタンジイル基などを挙げることができる。 Examples of the "C1 to 6 alkylene group" in A include a methylene group, a dimethylene group, a trimethylene group, and a tetramethylene group.
Examples of the "C2 to 6 alkenylene group" in A include a vinylene group (-CH = CH-), a divinylene group (-CH = CH-CH = CH-), and a propenylene group (-CH = CH-CH 2-, -CH). 2- CH = CH-) and the like can be mentioned.
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.

　本発明において、好ましいＡとしては、置換若しくは無置換のＣ１～６アルキレン基又は置換若しくは無置換のＣ２～６アルケニレン基を挙げることができる。
　Ｃ１～６アルキレン基又はＣ２～６アルケニレン基上の置換基としては、以下の置換基群より選択される１又は２以上の置換基を挙げることができる（以下、この置換基を記号「Ｇａ」で表すことがある。）。
　また、置換基（Ｇａ）は２以上ある場合、そのうちの２つが一緒になって二価の有機基を形成してもよい。以下に置換基群を示す。
　ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、メルカプト基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の３～６員環のヘテロシクリル基、置換若しくは無置換の３～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒａ１－ＣＯ－で表される基、カルボキシ基、Ｒｂ１－Ｏ－ＣＯ－で表される基、Ｒｃ１Ｒｄ１Ｎ－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－で表される基、Ｒａ１－ＣＯ－Ｏ－で表される基、Ｒａ１－ＣＯ－ＮＲｅ１－で表される基、Ｒｂ１－Ｏ－ＣＯ－Ｏ－で表される基、Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－Ｏ－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－ＮＲｅ１－で表される基、Ｒｂ１ＳＯ２－ＮＲｅ１－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＳＯ２－で表される基、Ｒａ１Ｏ－Ｎ＝ＣＲｆ１－で表される基、Ｒｇ１Ｒｈ１Ｃ＝Ｎ－Ｏ－で表される基、オキソ基（Ｏ＝）、チオキソ基（Ｓ＝）、Ｒａ１－Ｎ＝で表される二価の基、Ｒａ１Ｏ－Ｎ＝で表される二価の基、Ｒｃ１Ｒｄ１Ｎ－Ｎ＝で表される二価の基、Ｒａ１－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基、Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基、Ｒｂ１ＳＯ２－ＮＲｅ１－Ｎ＝で表される二価の基。 In the present invention, preferred A includes a substituted or unsubstituted C1 to 6 alkylene group or a substituted or unsubstituted C2 to 6 alkenylene group.
Examples of the 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. Alternatively, 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. Substituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 3 to 6-membered heterocyclyl group ring, a substituted or unsubstituted 3-6 membered heterocyclyloxy group ring, nitro group, cyano group, a group represented by R a1 -CO-, carboxy group, R b1 -O-CO- a group represented by, R c1 R d1 N- group represented by, R c1 R d1 N-CO-, a group represented by, R a1 -CO-O-, a group represented by, R a1 -CO- Group represented by NR e1- , group represented by R b1- O-CO-O-, group represented by R b1- O-CO-NR e1- , R c1 R d1 N-CO-O- The group represented by R c1 R d1 N-CO-NR e1- , the group represented by R b1 SO 2- NR e1- , and the group represented by R c1 R d1 N-SO 2-. Group, group represented by R a1 ON = CR f1- , group represented by R g1 R h1 C = NO-, oxo group (O =), thioxo group (S =), R a1- A divalent group represented by N =, a divalent group represented by R a1 ON =, a divalent group represented by R c1 R d1 NN =, R a1- CO-NR e1 A divalent group represented by -N =, a divalent group represented by R b1- O-CO-NR e1- N =, a divalent group represented by R b1 SO 2- NR e1- N = Group.

　上記の置換基群中、Ｒａ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｂ１は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｃ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｄ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、ここで、Ｒｃ１とＲｄ１は、一緒になって二価の有機基を形成してもよい。
　Ｒｅ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒｆ１は、水素原子、又は置換若しくは無置換のＣ１～６アルキル基を示し、
　Ｒｇ１は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｈ１は、水素原子、又は置換若しくは無置換のＣ１～６アルキル基を示し、ここで、Ｒｇ１とＲｈ１は、一緒になって二価の有機基を形成してもよい。 In the above substituent 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. Alternatively, 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.

　Ｇａにおける「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。 Examples of the "halogeno group" in Ga include a fluoro group, a chloro group, a bromo group, an iod group and the like.

　Ｇａにおける「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。Ｇａにおける「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。 The "C1-6 alkyl group" in Ga may be 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.

　Ｇａにおける「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基、２－プロペニル基、１－ブテニル基、２－ブテニル基、３－ブテニル基、１－メチル－２－プロペニル基、２－メチル－２－プロペニル基、１－ペンテニル基、２－ペンテニル基、３－ペンテニル基、４－ペンテニル基、１－メチル－２－ブテニル基、２－メチル－２－ブテニル基、１－ヘキセニル基、２－ヘキセニル基、３－ヘキセニル基、４－ヘキセニル基、５－ヘキセニル基などを挙げることができる。 The "C2-6 alkenyl group" in Ga includes a vinyl group, 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.

　Ｇａにおける「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基、２－プロピニル基、１－ブチニル基、２－ブチニル基、３－ブチニル基、１－メチル－２－プロピニル基、２－メチル－３－ブチニル基、１－ペンチニル基、２－ペンチニル基、３－ペンチニル基、４－ペンチニル基、１－メチル－２－ブチニル基、２－メチル－３－ペンチニル基、１－ヘキシニル基、１，１－ジメチル－２－ブチニル基などを挙げることができる。 The "C2-6 alkynyl group" in Ga includes 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.

　Ｇａにおける「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｎ－ブトキシ基、ｎ－ペンチルオキシ基、ｎ－ヘキシルオキシ基、ｉ－プロポキシ基、ｉ－ブトキシ基、ｓ－ブトキシ基、ｔ－ブトキシ基、ｉ－ヘキシルオキシ基などを挙げることができる。
　Ｇａにおける「Ｃ２～６アルケニルオキシ基」としては、ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などを挙げることができる。
　Ｇａにおける「Ｃ２～６アルキニルオキシ基」としては、エチニルオキシ基、プロパルギルオキシ基などを挙げることができる。 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.

　Ｇａにおける「Ｃ１～６アルキルチオ基」としては、メチルチオ基、エチルチオ基、ｎ－プロピルチオ基、ｎ－ブチルチオ基、ｎ－ペンチルチオ基、ｎ－ヘキシルチオ基、ｉ－プロピルチオ基などを挙げることができる。
　Ｇａにおける「Ｃ１～６アルキルスルフィニル基」としては、メチルスルフィニル基、エチルスルフィニル基、ｔ－ブチルスルフィニル基などを挙げることができる。
　Ｇａにおける「Ｃ１～６アルキルスルホニル基」としては、メチルスルホニル基、エチルスルホニル基、ｔ－ブチルスルホニル基などを挙げることができる。 Examples of the "C1 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.

　Ｇａにおける「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、「Ｃ２～６アルキニル基」、「Ｃ１～６アルコキシ基」、「Ｃ２～６アルケニルオキシ基」、「Ｃ２～６アルキニルオキシ基」、「Ｃ１～６アルキルチオ基」、「Ｃ１～６アルキルスルフィニル基」、又は「Ｃ１～６アルキルスルホニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；又はシアノ基が好ましい。 "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkynyloxy group" in 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. 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; 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 C6-10aryl group substituted with any one or more substituents of C1-6 haloalkoxy group; or cyano group is preferable.

　Ｇａにおける「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｇａにおける「Ｃ３～６シクロアルキルオキシ基」としては、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基などを挙げることができる。 Examples of the "C3 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.

　Ｇａにおける「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インデニル基、インダニル基、テトラリニル基などを挙げることができる。
　Ｇａにおける「Ｃ６～１０アリールオキシ基」としては、フェノキシ基、ナフトキシ基などを挙げることができる。 Examples of the "C6 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.

　Ｇａにおける「Ｃ６～１０アリールチオ基」としては、フェニルチオ基、ナフチルチオ基などを挙げることができる。
　Ｇａにおける「Ｃ６～１０アリールスルフィニル基」としては、フェニルスルフィニル基、ナフチルスルフィニル基などを挙げることができる。
　Ｇａにおける「Ｃ６～１０アリールスルホニル基」としては、フェニルスルホニル基、ナフチルスルホニル基などを挙げることができる。 Examples of the "C6 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.

　Ｇａにおける「３～６員環のヘテロシクリル基」とは、窒素原子、酸素原子及び硫黄原子からなる群から選ばれる１、２、３又は４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。「３～６員環のヘテロシクリル基」としては、３～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。 The "3- to 6-membered 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. ..

　３～６員環の飽和ヘテロシクリル基としては、アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～６員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基を挙げることができる。
　５～６員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；イソオキサゾリニル基、ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基を挙げることができる。 Examples of 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.

　Ｇａにおける「３～６員環のヘテロシクリルオキシ基」は、３～６員環のヘテロシクリル基とオキシ基が結合した構造を有する。具体例としては、チアゾリルオキシ基、ピリジルオキシ基などを挙げることができる。 The "3- to 6-membered 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.

　Ｇａにおける「Ｃ３～６シクロアルキル基」、「Ｃ３～６シクロアルキルオキシ基」、「Ｃ６～１０アリール基」、「Ｃ６～１０アリールオキシ基」、「Ｃ６～１０アリールチオ基」、「Ｃ６～１０アリールスルフィニル基」、「Ｃ６～１０アリールスルホニル基」、「３～６員環のヘテロシクリル基」、又は「３～６員環のヘテロシクリルオキシ基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；又はシアノ基が好ましい。 "C3-6 cycloalkyl group", "C3-6 cycloalkyloxy group", "C6-10 aryl group", "C6-10 aryloxy group", "C6-10 arylthio group", "C6-10" in 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; 4-methylphenyl group, 4-methoxyphenyl C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1-6, such as groups, 4-chlorophenyl groups, 4-trifluoromethylphenyl groups, 4-trifluoromethoxyphenyl groups, etc. A C6-10 aryl group substituted with any one or more substituents of the haloalkoxy group; or a cyano group is preferred.

　Ｇａにおける「Ｒａ１－ＣＯ－で表される基」中、Ｒａ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示す。 During the "group represented by R a1 -CO-" in Ga, 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.

　Ｒａ１における「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。
　Ｒａ１における「Ｃ２～６アルケニル基」としては、ビニル基、１－プロペニル基などを挙げることができる。
　Ｒａ１における「Ｃ２～６アルキニル基」としては、エチニル基、１－プロピニル基などを挙げることができる。
　Ｒａ１における「Ｃ１～６アルキル基」、「Ｃ２～６アルケニル基」、又は「Ｃ２～６アルキニル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのＣ３～６シクロアルキル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；又はシアノ基が好ましい。 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, cyclopentyl group, cyclohexyl group; phenyl group, naphthyl C6 to 10 aryl groups such as groups; any of halogeno groups, C1 to 6 haloalkyl groups, or C1 to 6 haloalkoxy groups such as 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group. A C6-10 aryl group substituted with one or more substituents; or a cyano group is preferred.

　Ｒａ１における「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｒａ１における「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基などを挙げることができる。 Examples of the "C3 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.

　Ｒａ１における「５～６員環のヘテロシクリル基」とは、窒素原子、酸素原子及び硫黄原子からなる群から選ばれる１、２、３又は４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。「５～６員環のヘテロシクリル基」としては、５～６員環の飽和ヘテロシクリル基、５～６員環のヘテロアリール基、５～６員環の部分不飽和ヘテロシクリル基などを挙げることができる。
　５～６員環の飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。　
　５～６員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基を挙げることができる。
　５～６員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；イソオキサゾリニル基、ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基を挙げることができる。 In 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.

　Ｒａ１における「Ｃ３～６シクロアルキル基」、「Ｃ６～１０アリール基」、又は「５～６員環のヘテロシクリル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；又はシアノ基が好ましい。 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, halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group. A C6-10 aryl group substituted with one or more substituents; or a cyano group is preferred.

　「Ｒａ１－ＣＯ－で表される基」の具体例としては、ホルミル基、アセチル基などを挙げることができる。 Specific examples of the "group represented by R a1 -CO-" may include formyl group, and acetyl group.

　Ｇａにおける「Ｒｂ１－Ｏ－ＣＯ－で表される基」中、Ｒｂ１は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示す。
　Ｒｂ１における置換基の具体例は、Ｒａ１において例示したものと同じものを挙げることができる。 Among the "groups represented by R b1- O-CO-" in Ga , 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.

　「Ｒｂ１－Ｏ－ＣＯ－で表される基」の具体例としては、メトキシカルボニル基、エトキシカルボニル基、ｔ－ブトキシカルボニル基などを挙げることができる。 Specific examples of the "group represented by R b1- O-CO-" include a methoxycarbonyl group, an ethoxycarbonyl group, a t-butoxycarbonyl group and the like.

　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－で表される基」中、Ｒｃ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、Ｒｄ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｃ１又はＲｄ１における置換基の具体例は、Ｒａ１において例示したものと同じものを挙げることができる。
　ここで、Ｒｃ１とＲｄ１は、一緒になって二価の有機基を形成してもよい。
形成できる二価の有機基としては、置換若しくは無置換のＣ２～５アルキレン基又は置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ２～５アルキレン基」としては、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ２～５アルキレン基」又は「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；又はクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。 Among the "groups represented by R c1 R d1 N-" in Ga , 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. C2 to 6 alkynyl groups, substituted or unsubstituted C3 to 6 cycloalkyl groups, substituted or unsubstituted C6 to 10 aryl groups, or substituted or unsubstituted 5- to 6-membered heterocyclyl groups, where R d1 is , Hydrogen atom, substituted or unsubstituted C1-6 alkyl group, or substituted or unsubstituted C6-10 aryl group.
Specific examples of the substituent in R c1 or R d1 can be the same as those exemplified in Ra1.
Here, 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.

　「Ｒｃ１Ｒｄ１Ｎ－で表される基」の具体例としては、アミノ基、メチルアミノ基、ジメチルアミノ基などを挙げることができる。 Specific examples of the "group represented by R c1 R d1 N-" include an amino group, a methylamino group, a dimethylamino group and the like.

　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－で表される基」中、Ｒｃ１及びＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－で表される基」の具体例としては、カルバモイル基、Ｎ，Ｎ－ジメチルアミノカルボニル基、Ｎ－（ｉ－プロピル）アミノカルボニル基、Ｎ－（ｉ－プロピル）－Ｎ－メチルアミノカルボニル基などを挙げることができる。 Among the "groups represented by R c1 R d1 N-CO-" in Ga , 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.

　Ｇａにおける「Ｒａ１－ＣＯ－Ｏ－で表される基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ１－ＣＯ－Ｏ－で表される基」の具体例としては、アセチルオキシ基などを挙げることができる。 During the "R a1 -CO-O- in group represented" in Ga, 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.

　Ｇａにおける「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　Ｒｅ１は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示す。
　Ｒｅ１における置換基の具体例は、Ｒａ１において例示したものと同じものを挙げることができる。
　「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」の具体例としては、アセチルアミノ基などを挙げることができる。 In "Group represented by R a1- CO-NR e1- " in Ga , 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.

　Ｇａにおける「Ｒｂ１－Ｏ－ＣＯ－Ｏ－で表される基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒｂ１－Ｏ－ＣＯ－Ｏ－で表される基」の具体例としては、メトキシカルボニルオキシ基、エトキシカルボニルオキシ基などを挙げることができる。 In "Group represented by R b1- O-CO-O-" in Ga , 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.

　Ｇａにおける「Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－で表される基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒa１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。
　「Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－で表される基」の具体例としては、メトキシカルボニルアミノ基などを挙げることができる。 In "Group represented by R b1- O-CO-NR e1- " in Ga , 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.

　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－Ｏ－で表される基」中、Ｒｃ１及びＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－Ｏ－で表される基」の具体例としては、カルバモイルオキシ基、Ｎ，Ｎ－ジメチルアミノカルボニルオキシ基などを挙げることができる。 Among the "groups represented by R c1 R d1 N-CO-O-" in Ga , R c1 and R d1 have the same meanings as those in the above " group represented by R c1 R d1 N-". ..
Specific examples of the "group represented by R c1 R d1 N-CO-O-" include a carbamoyloxy group and an N, N-dimethylaminocarbonyloxy group.

　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－ＮＲｅ１－で表される基」中、Ｒｃ１及びＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－ＣＯ－ＮＲｅ１－で表される基」の具体例としては、カルバモイルアミノ基、Ｎ，Ｎ－ジメチルアミノカルボニルアミノ基などを挙げることができる。 In "Groups represented by R c1 R d1 N-CO-NR e1- " in Ga , R c1 and R d1 have the same meanings as those in the above " Group represented by R c1 R d1 N-". Shown. 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.

　Ｇａにおける「Ｒｂ１ＳＯ２－ＮＲｅ１－で表される基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。
　「Ｒｂ１ＳＯ２－ＮＲｅ１－で表される基」の具体例としては、メタンスルホニルアミノ基などを挙げることができる。 In "Group represented by R b1 SO 2- NR e1- " in Ga , 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.

　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－ＳＯ２－で表される基」中、Ｒｃ１及びＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－ＳＯ２－で表される基」の具体例としては、Ｎ，Ｎ－ジメチルアミノスルホニル基などを挙げることができる。 Among the "groups represented by R c1 R d1 N-SO 2- " in Ga , R c1 and R d1 have the same meanings as those in the above " group represented by R c1 R d1 N-".
Specific examples of the "group represented by R c1 R d1 N-SO 2- " include an N, N-dimethylaminosulfonyl group and the like.

　Ｇａにおける「Ｒａ１Ｏ－Ｎ＝ＣＲｆ１－で表される基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　Ｒｆ１は、水素原子、又は置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｒｆ１における置換基の具体例は、Ｒａにおいて例示したものと同じものを挙げることができる。
　「Ｒａ１Ｏ－Ｎ＝ＣＲｆ１－で表される基」の具体例としては、（ヒドロキシイミノ）メチル基、（エトキシイミノ）メチル基などを挙げることができる。 In Ga - in "R a1 O-N = CR f1 represented by group", R a1 represents a similar meaning in "group represented by R a1 -CO-" above.
R f1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
Specific examples of the substituent in R f1 can be the same as those exemplified in Ra.
Specific examples of the "group represented by R a1 ON = CR f1- " include a (hydroxyimino) methyl group and a (ethoxyimino) methyl group.

　Ｇａにおける「Ｒｇ１Ｒｈ１Ｃ＝Ｎ－Ｏ－で表される基」中、Ｒｇ１は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、Ｒｈ１は、水素原子、又は置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｒｇ１又はＲｈ１における置換基の具体例は、Ｒａ１において例示したものと同じものを挙げることができる。
　ここで、Ｒｇ１とＲｈ１は、一緒になって二価の有機基を形成してもよい。
　形成できる二価の有機基としては、置換若しくは無置換のＣ２～５アルキレン基又は置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ２～５アルキレン基」としては、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ２～５アルキレン基」又は「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；　メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；又はクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。
　「Ｒｇ１Ｒｈ１Ｃ＝Ｎ－Ｏ－で表される基」の具体例としては、（プロパン－２－イリデンアミノ）オキシ基などを挙げることができる。 Among the "groups represented by R g1 R h1 C = NO-" in Ga , 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.
Specific examples of the substituent in R g1 or R h1 can be the same as those exemplified in Ra1.
Here, R g1 and R h1 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.
Specific examples of the "group represented by R g1 R h1 C = NO-" include a (propane-2-iridenamino) oxy group.

　Ｇａにおける「Ｒａ１－Ｎ＝で表される二価の基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ１－Ｎ＝で表される二価の基」の具体例としては、イミノ基（ＨＮ＝）、メチルイミノ基などを挙げることができる。 In "a divalent group represented by R a1- N =" in Ga , R a1 has the same meaning as that in the above-mentioned " group represented by R a1-CO-".
Specific examples of the "R a1 divalent group represented by -N =" represents an imino group (HN =), and the like methylimino group.

　Ｇａにおける「Ｒａ１Ｏ－Ｎ＝で表される二価の基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。
　「Ｒａ１Ｏ－Ｎ＝で表される二価の基」の具体例としては、Ｎ－ヒドロキシイミノ基、Ｎ－メトキシイミノ基などを挙げることができる。 During the "divalent group represented by R a1 O-N =" in Ga, R a1 represents a similar meaning in "group represented by R a1 -CO-" above.
Specific examples of the "divalent group represented by Ra1 ON =" include an N-hydroxyimino group and an N-methoxyimino group.

　Ｇａにおける「Ｒｃ１Ｒｄ１Ｎ－Ｎ＝で表される二価の基」中、Ｒｃ１及びＲｄ１は上記の「Ｒｃ１Ｒｄ１Ｎ－で表される基」におけるそれらと同様の意味を示す。
　「Ｒｃ１Ｒｄ１Ｎ－Ｎ＝で表される二価の基」の具体例としては、２，２－ジメチルヒドラジニリデン基などを挙げることができる。 In "a divalent group represented by R c1 R d1 N-N =" in Ga, R c1 and R d1 have the same meanings as those in the above " group represented by R c1 R d1 N-". Shown.
Specific examples of the "divalent group represented by R c1 R d1 NN =" include a 2,2-dimethylhydrazinilidene group.

　Ｇａにおける「Ｒａ１－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基」中、Ｒａ１は上記の「Ｒａ１－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。 In "a divalent group represented by R a1- CO-NR e1- N =" in Ga, 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-".

　Ｇａにおける「Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。 In "a divalent group represented by 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-".

　Ｇａにおける「Ｒｂ１ＳＯ２－ＮＲｅ１－Ｎ＝で表される二価の基」中、Ｒｂ１は上記の「Ｒｂ１－Ｏ－ＣＯ－で表される基」におけるそれと同様の意味を示す。Ｒｅ１は上記の「Ｒａ１－ＣＯ－ＮＲｅ１－で表される基」におけるそれと同様の意味を示す。 In "a divalent group represented by 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-".

　置換基（Ｇａ）が２以上ある場合に、そのうちの２つが一緒になって形成できる二価の有機基としては、置換若しくは無置換のＣ１～５アルキレン基、置換若しくは無置換のオキシＣ１～４アルキレン基、置換若しくは無置換のオキシＣ２～３アルキレンオキシ基、又は置換若しくは無置換のＣ１～３アルキレンオキシＣ１～３アルキレン基を挙げることができる。
　「Ｃ１～５アルキレン基」としては、メチレン基、ジメチレン基、トリメチレン基、テトラメチレン基などを挙げることができる。
　「オキシＣ１～４アルキレン基」としては、オキシメチレン基、オキシジメチレン基などを挙げることができる。
　「オキシＣ２～３アルキレンオキシ基」としては、オキシジメチレンオキシ基などを挙げることができる。
　「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」としては、ジメチレンオキシジメチレン基などを挙げることができる。
　「Ｃ１～５アルキレン基」、「オキシＣ１～４アルキレン基」、「オキシＣ２～３アルキレンオキシ基」、「Ｃ１～３アルキレンオキシＣ１～３アルキレン基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基などのＣ１～６アルキル基；又はクロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基が好ましい。 When there are two or more substituents (Ga), the divalent organic 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.

　本発明において、好ましいＧａとしては、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、Ｒａ１－ＣＯ－Ｏ－で表される基、オキソ基（Ｏ＝）、又はＲａ１Ｏ－Ｎ＝で表される二価の基を挙げることができる。
　この場合、好ましい置換若しくは無置換の５～６員環のヘテロシクリルオキシ基としては、テトラヒドロ－２Ｈ－ピラン－４－イル基を挙げることができる。 In the present invention, preferred Ga 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. of C3 ~ 6 cycloalkyl group, a substituted or unsubstituted C6 ~ 10 aryloxy group, a substituted or unsubstituted 5-6 membered heterocyclyloxy group ring, R a1 -CO-O-group represented by the oxo A divalent group represented by a group (O =) or Ra1 ON = can be mentioned.
In this case, the preferred substituted or unsubstituted 5- to 6-membered ring heterocyclyloxy group may include a tetrahydro-2H-pyran-4-yl group.

　本発明において、さらに好ましいＧａとしては、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、Ｒａ１－ＣＯ－Ｏ－で表される基、オキソ基（Ｏ＝）、又はＲａ１Ｏ－Ｎ＝で表される二価の基を挙げることができる。 In the present invention, more 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 −. CO-O-, a group represented by the oxo group (O =), or can be exemplified divalent group represented by R a1 O-N =.

　〔Ｙ〕
　Ｙは、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～１０員環のヘテロシクリル基を示す。 [Y]
Y represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 10-membered ring heterocyclyl group.

　Ｙにおける「Ｃ６～１０アリール基」としては、フェニル基、ナフチル基、インデニル基、インダニル基、テトラリニル基などを挙げることができる。 Examples of the "C6 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.

　Ｙにおける「５～１０員環のヘテロシクリル基」とは、窒素原子、酸素原子及び硫黄原子からなる群から選ばれる１、２、３又は４個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が２個以上であるとき、それらは同じでもよいし、異なってもよい。単環及び多環のいずれでもよい。
　「５～１０員環のヘテロシクリル基」としては、５～６員環の飽和ヘテロシクリル基、５～１０員環のヘテロアリール基、５～１０員環の部分不飽和ヘテロシクリル基などを挙げることができる。 The "5- to 10-membered 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. ..

　５～６員環の飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
　５～１０員環のヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；インドリル基、イソインドリル基、ベンゾフラニル基、ベンゾチエニル基、インダゾリル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾイソオキサオゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基などの９員ヘテロアリール基；キノリニル基、イソキノリニル基、シンノリニル基、フタラジニル基、キナゾリニル基、キノキサリニル基などの１０員ヘテロアリール基；を挙げることができる。
　５～１０員環の部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基などの５員環の部分不飽和ヘテロシクリル基；イソオキサゾリニル基、ジヒドロピラニル基などの６員環の部分不飽和へテロシクリル基；インドリニル基、イソインドリニル基、２，３－ジヒドロベンゾフラニル基、１，３－ジヒドロベンゾフラニル基などの９員環の部分不飽和ヘテロシクリル基；１，２，３，４－テトラヒドロキノリニル基などの１０員環の部分不飽和ヘテロシクリル基；を挙げることができる。 Examples of 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, pyridadinyl 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. 10-membered heteroaryl group;
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.

　Ｙにおける「Ｃ６～１０アリール基」又は「５～１０員環のへテロシクリル基」上の置換基としては、フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メチル基、エチル基、ｎ－プロピル基、ｉ－プロピル基、ｎ－ブチル基、ｓ－ブチル基、ｉ－ブチル基、ｔ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基などのＣ１～６アルキル基；ビニル基などのＣ２～６アルケニル基；エチニル基などのＣ２～６アルキニル基；クロロメチル基、クロロエチル基、トリフルオロメチル基、１，２－ジクロロ－ｎ－プロピル基、１－フルオロ－ｎ－ブチル基などのＣ１～６ハロアルキル基；メトキシメチル基などのＣ１～６アルコキシＣ１～６アルキル基；水酸基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；ヒドロキシエトキシ基などのヒドロキシＣ１～６アルコキシ基；メトキシメトキシ基、メトキシエトキシ基などのＣ１～６アルコキシアルコキシ基；トリメチルシリルオキシエトキシ基、ｔ－ブチルジメチルシリルオキシエトキシ基などのトリＣ１～６アルキル置換シリルオキシＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；Ｃ３～６シクロアルキルＣ１～６アルコキシ基；Ｃ６～１０アリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルコキシ基；５員環のヘテロアリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環のヘテロアリール）Ｃ１～６アルコキシ基；６員環のヘテロアリールＣ１～６アルコキシ基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール）Ｃ１～６アルコキシ基；メチルチオ基、エチルチオ基などのＣ１～６アルキルチオ基：メチルスルフィニル基、エチルスルフィニル基などのＣ１～６アルキルスルフィニル基；メチルスルホニル基、エチルスルホニル基などのＣ１～６アルキルスルホニル基；トリフルオロメチルチオ基、２，２，２－トリフルオロエチルチオ基などのＣ１～６ハロアルキルチオ基：トリフルオロメチルスルフィニル基、２，２，２－トリフルオロエチルスルフィニル基などのＣ１～６ハロアルキルスルフィニル基；トリフルオロメチルスルホニル基、２，２，２－トリフルオロエチルスルホニル基などのＣ１～６ハロアルキルスルホニル基；シクロプロピル基、シクロブチル基、シクロペンチル基などのＣ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、又はシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；シクロプロぺニル基、シクロブテニル基、シクロペンテニル基などのＣ３～６シクロアルケニル基；フェニル基、ナフチル基などのＣ６～１０アリール基；４－メチルフェニル基、４－メトキシフェニル基、４－クロロフェニル基、４－フルオロフェニル基、４－トリフルオロメチルフェニル基、４－トリフルオロメトキシフェニル基などの、Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；アジリジニル基、エポキシ基、アゼチジニル基、オキセタニル基などの３～４員環の飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された３～４員環の飽和ヘテロシクリル基；ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ－２Ｈ－ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などの５～６員環の飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環の飽和ヘテロシクリル基；ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基など５員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基でのいずれか１以上の置換基で置換された５員環のヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員環のヘテロアリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環のヘテロアリール基；ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基などの５員環の部分不飽和へテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５員環の部分飽和ヘテロシクリル基；イソオキサゾリニル基、ジヒドロピラニル基などの６員環の部分不飽和ヘテロシクリル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、又はＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された６員環の部分飽和ヘテロシクリル基； 
ＲY１－ＣＯ－で表される基　（式中、ＲY１は、水素原子；Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；Ｃ２～６アルケニル基；Ｃ２～６ハロアルケニル基；Ｃ２～６アルキニル基；Ｃ２～６ハロアルキニル基；Ｃ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、若しくはシアノ基のいずれか１以上の置換基で置換されたＣ３～６シクロアルキル基；Ｃ６～１０アリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；５～６員環のヘテロアリール基；又は；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール基；を示す。以下のＲY１においても同じ。）；
カルボキシ基；
ＲY２－Ｏ－ＣＯ－で表される基　（式中、ＲY２は、Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；Ｃ２～６アルケニル基；Ｃ２～６ハロアルケニル基；Ｃ２～６アルキニル基；Ｃ２～６ハロアルキニル基；Ｃ３～６シクロアルキル基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、Ｃ１～６ハロアルコキシ基、若しくはシアノ基で置換されたＣ３～６シクロアルキル基；Ｃ６～１０アリール基；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール基；５～６員環のヘテロアリール基；又は；Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール基；を示す。以下のＲY２においても同じ。）；
ＲY１ＲY１Ｎ－で表される基（式中のＲY１は同一でも異なっていてもよい。ＲY１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、又はジメチレンオキシジメチレン基を形成してもよい。）；
ＲY１ＲY１Ｎ－ＣＯ－で表される基（式中のＲY１は同一でも異なっていてもよい。ＲY１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、又はジメチレンオキシジメチレン基を形成してもよい。）；
ＲY１－ＣＯ－Ｏ－で表される基；ＲY１－ＣＯ－ＮＲY３－で表される基（式中、ＲY３は、水素原子；Ｃ１～６アルキル基；ハロゲノ基、Ｃ１～６アルコキシ基、Ｃ１～６ハロアルコキシ基、Ｃ３～６シクロアルキル基、フェニル基、若しくは５～６員環のヘテロアリール基のいずれか１以上の置換基で置換されたＣ１～６アルキル基；（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換されたＣ６～１０アリール）Ｃ１～６アルキル基；又は（Ｃ１～６アルキル基、Ｃ１～６アルコキシ基、ハロゲノ基、Ｃ１～６ハロアルキル基、若しくはＣ１～６ハロアルコキシ基のいずれか１以上の置換基で置換された５～６員環のヘテロアリール）Ｃ１～６アルキル基；を示す。以下のＲY３においても同じ。）；
ＲY２－Ｏ－ＣＯ－Ｏ－で表される基；ＲY２－Ｏ－ＣＯ－ＮＲY３－で表される基；ＲY１ＲY１Ｎ－ＣＯ－Ｏ－で表される基（式中のＲY１は同一でも異なっていてもよい。ＲY１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、又はジメチレンオキシジメチレン基を形成してもよい。）；
ＲY１ＲY１Ｎ－ＣＯ－ＮＲY３－で表される基（式中のＲY１は同一でも異なっていてもよい。ＲY１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、又はジメチレンオキシジメチレン基を形成してもよい。）；ＲY２ＳＯ２－ＮＲY３－で表される基；ＲY１ＲY１Ｎ－ＳＯ２－で表される基（式中のＲY１は同一でも異なっていてもよい。ＲY１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、又はジメチレンオキシジメチレン基を形成してもよい。）；
ＲY１－Ｏ－Ｎ＝Ｃ（ＲY４）－で表される基（式中、ＲY４は、水素原子又はＣ１～６アルキル基を示す。）；（ＲY１）２Ｃ＝Ｎ－Ｏ－で表される基（式中のＲY１は同一でも異なっていてもよい。ＲY１同士は一緒になって、トリメチレン基、テトラメチレン基、ペンタメチレン基、又はジメチレンオキシジメチレン基を形成してもよい。）；
　ペンタフルオロスルファニル基、トリメチルシリルエチニル基、ニトロ基、又はシアノ基が好ましい。
　さらに、「５～１０員環のヘテロシクリル基」上の置換基としては、オキソ基も好ましい。 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; 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; C6-10aryl C1-6 alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or C1-6 halo C6 to 10 aryl) C1 to 6 alkoxy groups substituted with any one or more of the alkoxy groups; 5-membered ring heteroaryl C1 to 6 alkoxy groups; (C1 to 6 alkyl groups, C1 to 6 alkoxy groups, 5-membered ring heteroaryl substituted with one or more substituents of a halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group) C1-6 alkoxy group; 6-membered ring heteroaryl C1-6 Alkoxy group; (C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, or 6-membered ring heteroaryl substituted with any one or more substituents of C1-6 haloalkoxy group ) C1-6 alkoxy groups; C1-6 alkylthio groups such as methylthio group and ethylthio group: C1-6 alkylsulfy such as methylsulfinyl group and ethylsulfinyl group Nyl group; C1-6 alkylsulfonyl group such as methylsulfonyl group, ethylsulfonyl group; C1-6 haloalkylthio group such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group: trifluoromethylsulfinyl group, C1-6 haloalkylsulfinyl groups such as 2,2,2-trifluoroethylsulfinyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups, 2,2,2-trifluoroethylsulfonyl groups; cyclopropyl groups, C3 to 6 cycloalkyl groups such as cyclobutyl group and cyclopentyl group; any one or more of C1 to 6alkyl groups, C1 to 6 alkoxy groups, halogeno groups, C1 to 6 haloalkyl groups, C1 to 6 haloalkoxy groups, or cyano groups. C3-6 cycloalkyl groups substituted with the substituents of; C3-6 cycloalkenyl groups such as cyclopropenyl group, cyclobutenyl group, cyclopentenyl group; C6-10aryl groups such as phenyl group, naphthyl group; 4-methyl C1-6 alkyl groups, C1-6 alkoxy groups, such as phenyl group, 4-methoxyphenyl group, 4-chlorophenyl group, 4-fluorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc. 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; A saturated heterocyclyl group having a 5- to 6-membered ring substituted with any one or more substituents of a C1 to 6 alkyl group, a C1 to 6 alkoxy group, a halogeno group, a C1 to 6 haloalkyl group, or a C1 to 6 haloalkoxy group; Pyrrolyl group, frill group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isooxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl Heteroaryl group having a 5-membered ring such as a group; substituted with any one or more substituents of a C1 to 6 alkyl group, a C1 to 6 alkoxy group, a halogeno group, a C1 to 6 haloalkyl group, or a C1 to 6 haloalkoxy group. 5-membered heteroaryl 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. 5-membered partially saturated heterocyclyl group; 6-membered partially unsaturated heterocyclyl group such as isooxazolinyl group, dihydropyranyl group; C1-6alkyl group, C1-6alkoxy group, halogeno group, C1-6haloalkyl A partially saturated heterocyclyl group of a 6-membered ring substituted with one or more substituents of a group or a C1 to 6 haloalkoxy group;
Group (wherein represented by R Y1 -CO-, R Y1 is a hydrogen atom; C1 ~ 6 alkyl group; a halogeno group, C1 ~ 6 alkoxy group, C1 ~ 6 haloalkoxy group, C3 ~ 6 cycloalkyl group, C1-6 alkyl groups substituted with any one or more substituents of a phenyl group or a 5- to 6-membered heteroaryl group; (C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 C6 to 10 aryl substituted with any one or more substituents of a haloalkyl group or a C1 to 6 haloalkoxy group) C1 to 6 alkyl groups; (C1 to 6 alkyl groups, C1 to 6 alkoxy groups, halogeno groups, C1 A 5- to 6-membered ring heteroaryl substituted with any one or more substituents of the ~ 6 haloalkyl group or the C1-6 haloalkoxy group) C1-6 alkyl group; C2-6 alkenyl group; C2-6 haloalkenyl Group; C2-6 alkynyl group; C2-6 haloalkynyl group; C3-6 cycloalkyl group; C1-6 alkyl group, C1-6 alkoxy group, halogeno group, C1-6 haloalkyl group, C1-6 haloalkoxy group, Alternatively, a C3 to 6 cycloalkyl group substituted with any one or more substituents of the cyano group; a C6 to 10 aryl group; a C1 to 6 alkyl group, a C1 to 6 alkoxy group, a halogeno group, a C1 to 6 haloalkyl group, or C6-10 aryl group substituted with any one or more substituents of C1-6 haloalkoxy groups; 5-6-membered ring heteroaryl group; or; C1-6 alkyl group, C1-6 alkoxy group, halogeno group , A 5- to 6-membered heteroaryl group substituted with any one or more substituents of the C1 to 6 haloalkyl group or the C1 to 6 haloalkoxy group; the same applies to RY1 below.);
Carboxylic acid group;
Group (wherein represented by R Y2 -O-CO-, R Y2 is, C1 ~ 6 alkyl group; a halogeno group, C1 ~ 6 alkoxy group, C1 ~ 6 haloalkoxy group, C3 ~ 6 cycloalkyl group, phenyl C1-6 alkyl groups substituted with any one or more substituents of groups or 5- to 6-membered heteroaryl groups; (C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyls C6 to 10 aryl substituted with any one or more substituents of the group or C1 to 6 haloalkoxy groups) C1 to 6 alkyl groups; (C1 to 6 alkyl groups, C1 to 6 alkoxy groups, halogeno groups, C1 to C1 to A 5- to 6-membered heteroaryl substituted with any one or more substituents of a 6-haloalkyl group or a C1 to 6 haloalkoxy group) C1 to 6 alkyl groups; C2 to 6 alkenyl groups; C2 to 6 haloalkenyl groups C2-6 alkynyl groups; C2-6 haloalkynyl groups; C3-6 cycloalkyl groups; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, C1-6 haloalkenyl groups, or C3 to 6 cycloalkyl groups substituted with cyano groups; C6 to 10 aryl groups; C1 to 6 alkyl groups, C1 to 6 alkoxy groups, halogeno groups, C1 to 6 haloalkyl groups, or C1 to 6 haloalkoxy groups. C6-10 aryl groups substituted with one or more substituents; 5-6-membered ring heteroaryl groups; or; C1-6 alkyl groups, C1-6 alkoxy groups, halogeno groups, C1-6 haloalkyl groups, or C1 Shows a 5- to 6-membered heteroaryl group substituted with any one or more substituents of the ~ 6 haloalkoxy groups; the same applies to the following RY2);
R Y1 R Y1 R Y1 group (wherein represented by N- good .R Y1 together be the same or different, together, trimethylene group, tetramethylene group, pentamethylene group, or a di-methyleneoxy A dimethylene group may be formed.);
R Y1 good .R Y1 together be the same or different in R Y1 R Y1 N-CO-, a group represented by (wherein together, trimethylene group, tetramethylene group, pentamethylene group, or a di Methyleneoxydimethylene groups may be formed.);
R Y1 -CO-O- in group represented; R Y1 -CO-NR Y3 - group (wherein represented by, R Y3 represents a hydrogen atom; C1 ~ 6 alkyl group; a halogeno group, C1 ~ 6 alkoxy A C1-6 alkyl group substituted with any one or more substituents of a group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group, a phenyl group, or a 5- to 6-membered heteroaryl group; C6 to 10 aryl) C1 to 6 alkyl groups substituted with any one or more substituents of 6 alkyl group, C1 to 6 alkoxy group, halogeno group, C1 to 6 haloalkyl group, or C1 to 6 haloalkoxy group; or (A heteroaryl of a 5- to 6-membered ring substituted with any one or more substituents of a C1 to 6 alkyl group, a C1 to 6 alkoxy group, a halogeno group, a C1 to 6 haloalkyl group, or a C1 to 6 haloalkoxy group) C1 to 6 alkyl groups; are shown. The same applies to RY3 below.);
R Y2 -O-CO-O- in group represented; R Y2 -O-CO-NR Y3 - a group represented by; R Y1 R Y1 N-CO -O- , a group represented by (in the formula R Y1 together good .R Y1 together be the same or different, trimethylene group, tetramethylene group, may form a pentamethylene group, or a di-methyleneoxy dimethylene group).;
R Y1 R Y1 N-CO- NR Y3 - R Y1 good .R Y1 together be the same or different groups (wherein represented by together, trimethylene group, tetramethylene group, pentamethylene group , or may form a dimethylene oxy dimethylene group);. R Y2 SO 2 -NR Y3 - group represented by; R Y1 R Y1 N-SO 2 - group represented by (R in the formula Y1 is good .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) - (. Wherein, R Y4 represents a hydrogen atom or a C1 ~ 6 alkyl group) a group represented by; (R Y1) 2 C = N-O- in the R Y1 group (wherein represented good .R Y1 together be the same or different, together, trimethylene group, tetramethylene group, to form a pentamethylene group, or a di-methyleneoxy dimethylene group May be.);
Pentafluorosulfanil groups, trimethylsilylethynyl groups, nitro groups, or cyano groups are preferred.
Further, as the substituent on the "5- to 10-membered heterocyclyl group", an oxo group is also preferable.

〔Ｑ〕
　式（II）中、Ｑは、式（Ｑ－１）又は式（Ｑ－２）で表される基である。 [Q]
In formula (II), Q is a group represented by formula (Q-1) or formula (Q-2).

Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000021
Figure JPOXMLDOC01-appb-C000022
Figure JPOXMLDOC01-appb-C000022

　式（Ｑ－１）及び式（Ｑ－２）中、矢印は結合部位を示す。
式（Ｑ－１）及び式（Ｑ－２）中、Ｒcは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、Ｃ１～６アルキルアミノ基又は置換若しくは無置換のＣ３～６シクロアルキル基である。Ｒｄ は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ１～６アルキルカルボニル基である。 In formulas (Q-1) and (Q-2), arrows indicate binding sites.
In formulas (Q-1) and (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.

　Ｒc 及びＲd における「置換若しくは無置換のＣ１～６アルキル基」としては、Ｘ１’において具体的に例示したそれらと同じものを挙げることができ、「置換若しくは無置換のＣ１～６アルコキシ基」としては、Ｘ７において具体的に例示したそれらと同じものを挙げることができる。 Examples of the "substituted or unsubstituted C1 to 6 alkyl groups" in R c and R d include the same ones specifically exemplified in X 1' , and "substituted or unsubstituted C1 to 6 alkoxy" can be mentioned. the group "may include the same as those concretely exemplified in the X 7.

　Ｒcにおける「Ｃ１～６アルキルアミノ基」としては、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などを挙げることができる。Ｒcにおける「Ｃ１～６アルキルアミノ基」上の置換基として、好ましくは、Ｃ１～６ アルキル基を挙げることができる。「Ｃ１～６アルキル基」としては、Ｒ1において具体的に例示したそれらと同じものを挙げることができる。 Examples of the "C1 to 6 alkylamino group" in Rc include a methylamino group, a dimethylamino group, a diethylamino group and the like. As 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.

　Ｒcにおける「Ｃ３～６シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
　Ｒcにおける「Ｃ３～６シクロアルキル基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；シアノ基を挙げることができる。 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.
As 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.

　Ｒｄ における「Ｃ１～６アルキルカルボニル基」としては、アセチル基、プロピオニル基、イソプロピルカルボニル基などを挙げることができる。
Ｒｄにおける「Ｃ１～６アルキルカルボニル基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；シアノ基を挙げることができる。 Examples of the "C1 to 6 alkylcarbonyl group" in R d include an acetyl group, a propionyl group, an isopropylcarbonyl group and the like.
As 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.

〔Ｘ１’〕
　式（II）中、Ｘ１’は、置換若しくは無置換のＣ１～６アルコキシカルボニル基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換の５～６員ヘテロアリール基、シアノ基、又は式「－ＣＲa’ ＝Ｎ－ＯＲb’ 」で表される基である。 [X 1' ]
Wherein (II), X 1 'is a substituted or unsubstituted C1 ~ 6 alkoxycarbonyl group, a substituted or unsubstituted C1 ~ 6 alkyl group, a substituted or unsubstituted 5-6 membered heteroaryl group, a cyano group, Alternatively, it is a group represented by the formula "-CR a' = N-OR b'".

　Ｘ１’における「Ｃ１～６アルコキシカルボニル基」としては、メトキシカルボニル基、エトキシカルボニル基、ｎ－プロポキシカルボニル基、ｉ－プロポキシカルボニル基、ｎ－ブトキシカルボニル基、ｔ－ブトキシカルボニル基などを挙げることができる。 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.

　Ｘ１’における「Ｃ１～６アルコキシカルボニル基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基を挙げることができる。 As the substituent on the "C1-6 alkoxycarbonyl group" in X 1', a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be preferably mentioned.

　Ｘ１’における「Ｃ１～６アルキル基」としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。 As "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.

　Ｘ１’における「Ｃ１～６アルキル基」上の置換基として、好ましくは水酸基；メトキシ基、エトキシ基などのＣ１～６アルコキシ基を挙げることができる。 As the substituent on the "C1 to 6 alkyl group" in X 1' , preferably, a C1 to 6 alkoxy group such as a hydroxyl group; a methoxy group or an ethoxy group can be mentioned.

　Ｘ１’における「５～６員ヘテロアリール基」としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などの５員ヘテロアリール基；ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などの６員ヘテロアリール基を挙げることができる。 As "5- to 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.

　Ｘ１’における「５～６員ヘテロアリール基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基を挙げることができる。 As the substituent on the "5- to 6-membered heteroaryl group" in X 1', a halogeno group such as a fluoro group, a chloro group, a bromo group and an iod group can be preferably mentioned.

　Ｘ１’における「式：「－ＣＲa’ ＝Ｎ－ＯＲb’ 」で表される基」中のＲa’ は、水素原子又はアミノ基であり、Ｒb ’は、水素原子又は置換若しくは無置換のＣ１～６アルキル基である。
　Ｒb ’における「Ｃ１～６アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。アルキル基としては、メチル基、エチル基、ｎ－プロピル基、ｎ－ブチル基、ｎ－ペンチル基、ｎ－ヘキシル基、ｉ－プロピル基、ｉ－ブチル基、ｓ－ブチル基、ｔ－ブチル基、ｉ－ペンチル基、ネオペンチル基、２－メチルブチル基、ｉ－ヘキシル基などを挙げることができる。 'In the "formula" - CR a' X 1 'R a of a group represented by "in = N-OR b''is a hydrogen atom or an amino group, R b' is a hydrogen atom or a substituted or It is an unsubstituted C1-6 alkyl group.
The "C1-6 alkyl group" in R b'may be a straight chain or a branched chain. 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.

　Ｘ１’における「式：「－ＣＲa’ ＝Ｎ－ＯＲb’ 」で表される基」としては、メトキシイミノメチル基、エトキシイミノメチル基、ｎ－プロポキシイミノメチル基、イソプロポキシイミノメチル基などを挙げることができる。 'In the "formula" - CR a' X 1 as = N-OR b 'group represented by "" are methoxyiminomethyl group, an ethoxy imino methyl group, n- propoxy alkoximinoalkyl amino methyl, isopropoxycarbonyl alkoximinoalkyl amino methyl And so on.

〔Ｘ２’〕
　式（II）中、Ｘ２’は、置換若しくは無置換のＣ１～６アルキル基である。 [X 2' ]
Wherein (II), X 2 'is a substituted or unsubstituted C1 ~ 6 alkyl group.

　Ｘ２’における「置換若しくは無置換のＣ１～６アルキル基」としては、Ｘ１’において具体的に例示したそれらと同じものを挙げることができる。 'As the "substituted or unsubstituted C1 ~ 6 alkyl group" in, X 1' X 2 can be cited the same as those concretely exemplified in the.

　Ｘ２’における「Ｃ１～６アルキル基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などのＣ１～６アルコキシ基；２－クロロ－ｎ－プロポキシ基、２，３－ジクロロブトキシ基、トリフルオロメトキシ基などのＣ１～６ハロアルコキシ基；シアノ基を挙げることができる。 As the substituent on the "C1-6 alkyl group" in X 2', 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.

　〔Ｘ７〕
　式（II）中、Ｘ７ は、水酸基、置換若しくは無置換のＣ１～６アルコキシ基又は置換若しくは無置換のＣ１～６アルキルカルボニルオキシ基である。
　Ｘ７ における「Ｃ１～６アルコキシ基」としては、メトキシ基、エトキシ基、ｎ－プロポキシ基、ｉ－プロポキシ基、ｎ－ブトキシ基、ｓ－ブトキシ基、ｉ－ブトキシ基、ｔ－ブトキシ基などを挙げることができる。 [X 7 ]
In formula (II), 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.

　Ｘ７ における「Ｃ１～６アルキルカルボニルオキシ基」としては、アセチルオキシ基、プロピオニルオキシ基などを挙げることができる。
　Ｘ７ における「Ｃ１～６アルコキシ基」及び「Ｃ１～６アルキルカルボニルオキシ基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基；メトキシ基、エトキシ基などのＣ１～６アルコキシ基；シアノ基を挙げることができる。 The "C1 ~ 6 alkyl-carbonyl group" in X 7, and the like acetyloxy group, propionyloxy group.
As 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.

〔Ｘ８〕
　式（II）中、Ｘ８ は、水素原子である。
　Ｘ７ とＸ８ は、それらが一緒になって、オキソ基、又は置換若しくは無置換のＣ１～６アルコキシイミノ基を形成してもよい。
　Ｘ７ とＸ８が一緒になって形成する「Ｃ１～６アルコキシイミノ基」としては、メトキシイミノ基、エトキシイミノ基が挙げられる。
　Ｘ７ とＸ８が一緒になって形成する「Ｃ１～６アルコキシイミノ基」上の置換基として、好ましくはフルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基を挙げることができる。 [X 8 ]
In formula (II), 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.

〔Ｘ９〕〔Ｘ１０〕
　Ｘ９ 及びＸ１０ は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基である。 [X 9 ] [X 10 ]
X 9 and X 10 are independently hydrogen atoms or substituted or unsubstituted C1-6 alkyl groups.

　Ｘ８とＸ１０ は、それらが一緒になって、単結合を形成してもよい。
　単結合を形成する化合物として式（III）が挙げられる。

Figure JPOXMLDOC01-appb-C000023
　式（III）におけるＸ１’、Ｘ２’、Ｘ３、Ｘ４、Ｘ５、Ｘ６、Ｘ７、Ｘ９、Ｘ１１、ｎ、Ｑの各記号は、各記号は、式（II）のものと同じものを意味する。 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.
Figure JPOXMLDOC01-appb-C000023
 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.

　〔Ｘ１１〕
　式（II）中、Ｘ１１は、ハロゲノ基又は置換若しくは無置換のＣ１～６アルコキシ基である。
　Ｘ１１における「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。
　Ｘ１１における「置換若しくは無置換のＣ１～６アルコキシ基」としては、Ｘ７において具体的に例示したそれらと同じものを挙げることができる。 [X 11 ]
In formula (II), X 11 is a halogeno group or a substituted or unsubstituted C1-6 alkoxy group.
Examples of the "halogeno group" in X 11 include a fluoro group, a chloro group, a bromo group, an iod group and the like.
Examples of the "substituted or unsubstituted C1 to 6 alkoxy groups" in X 11 include the same groups specifically exemplified in X 7.

　〔ｎ〕
　式（II）中、ｎは、０～５のいずれかの整数であり、ｎが２以上のときＸ１１は互いに同じでも異なってもよい。 [N]
In formula (II), 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.

　〔塩〕
　化合物（Ｉ）及び化合物（II）の塩は、農園芸学的に許容される塩であれば、特に制限されない。例えば、塩酸、硫酸などの無機酸の塩；酢酸、乳酸などの有機酸の塩；リチウム、ナトリウム、カリウムなどのアルカリ金属の塩；カルシウム、マグネシウムなどのアルカリ土類金属の塩；鉄、銅などの遷移金属の塩；トリエチルアミン、トリブチルアミン、ピリジン、ヒドラジンなどの有機塩基の塩；アンモニアなどを挙げることができる。 〔salt〕
The salts of compound (I) and compound (II) are not particularly limited as long as they are horticulturally acceptable salts. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron, copper and the like. Transition metal salts; salts of organic bases such as triethylamine, tributylamine, pyridine, hydrazine; ammonia and the like.

　〔製造方法〕
　化合物（Ｉ）及び化合物（II）で表される化合物又はその塩の製造方法は、限定されない。例えば、本発明の化合物（Ｉ）及び化合物（II）で表される化合物又はその塩は、実施例等に記載したような公知の手法によって得ることができる。また、化合物（Ｉ）及び化合物（II）の塩は、化合物（Ｉ）及び化合物（II）から公知の手法によって得ることができる。 〔Production method〕
The method for producing the compound (I) and the compound represented by the compound (II) or a salt thereof is not limited. For example, 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. Further, the salts of compound (I) and compound (II) can be obtained from compound (I) and compound (II) by a known method.

　〔製造中間体〕
下記式（IV）及び式（V）で表される化合物又はその塩は、式（Ｉ）及び式（II）で表される化合物を製造する際の製造中間体として用いることが可能である。 [Manufacturing intermediate]
The compounds represented by the following formulas (IV) and (V) or salts thereof can be used as production intermediates when producing the compounds represented by the formulas (I) and (II).

Figure JPOXMLDOC01-appb-C000024
式（IV）中、　Ｘ１、Ｘ２、Ｘ３、Ｘ４、Ｘ５、Ｘ６、Ａ、Ｙの各記号は、それぞれ式（I）と同じものを意味する。
　Ｑ’は、ＮＨ２又は ＣＨ２ＮＨ２で表される基である。
Figure JPOXMLDOC01-appb-C000024
 In formula (IV), the symbols X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , A, and Y mean the same as in formula (I), respectively.
Q'is a group represented by NH 2 or CH 2 NH 2.

Figure JPOXMLDOC01-appb-C000025
Figure JPOXMLDOC01-appb-C000025

　　式（V）中、　Ｘ１’、Ｘ２’、Ｘ３、Ｘ４、Ｘ５、Ｘ６、Ｘ７、Ｘ８、Ｘ９、Ｘ１０、Ｘ１１、nの各記号は、それぞれ式（II）と同じものを意味する。
　　Ｑ’は、ＮＨ２又は ＣＨ２ＮＨ２で表される基である。 In formula (V), the symbols of X 1' , X 2' , X 3 , X 4 , X 5 , X 6 , X 7 , X 8 , X 9 , X 10 , X 11 , and n are the formulas (V). It means the same thing as II).
Q'is a group represented by NH 2 or CH 2 NH 2.

　本発明の化合物（Ｉ）及び化合物（II）の製造に用いる製造中間体の一例を以下の表１に示す。表中には、各化合物の物性として融点（m.p.）を併せて示す。 Table 1 below shows an example of the production intermediate used for producing the compound (I) and the compound (II) of the present invention. In the table, the melting point (m.p.) is also shown as the physical characteristics of each compound.

Figure JPOXMLDOC01-appb-T000026
　表１に記載した化合物のうち、非晶又は粘性オイルの性状を有する化合物については、下記にその１Ｈ－ＮＭＲデータを示す。
　化合物１：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）： 7.95 (2H, br s), 7.62-7.61 (1H, m), 7.30-7.26 (1H, m), 7.04-7.01 (1H, m), 5.30 (2H, d, J = 5.4 Hz), 4.32-4.29 (2H, m), 4.18-4.16 (2H, m), 4.03-4.02 (3H, m), 4.02 (2H, m), 3.02-2.99 (2H, m), 2.17 (3H, s), 1.33 (3H, t, J = 7.1 Hz).
Figure JPOXMLDOC01-appb-T000026
 Among the compounds listed in Table 1, the compounds having amorphous or viscous oil properties are shown below in 1 H-NMR data.
Compound 1: 1 1 H-NMR (CDCl 3 , δppm): 7.95 (2H, br s), 7.62-7.61 (1H, m), 7.30-7.26 (1H, m), 7.04-7.01 (1H, m), 5.30 (2H, d, J = 5.4 Hz), 4.32-4.29 (2H, m), 4.18-4.16 (2H, m), 4.03-4.02 (3H, m), 4.02 (2H, m), 3.02-2.99 (2H) , m), 2.17 (3H, s), 1.33 (3H, t, J = 7.1 Hz).

　〔農園芸用殺菌剤〕
　本発明の農園芸用殺菌剤は、化合物（Ｉ）及び化合物（II）で表される化合物又はその塩からなる群から選ばれる少なくとも１つを有効成分として含有するものである。本発明の農園芸用殺菌剤に含まれる化合物（Ｉ）及び化合物（II）で表される化合物又はその塩の量は殺菌効果を示す限りにおいて特に制限されない。 [Agricultural and horticultural fungicides]
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.

　本発明の農園芸用殺菌剤は、広範囲の種類の糸状菌、例えば、藻菌類（Oomycetes）、子のう（嚢）菌類（Ascomycetes）、不完全菌類（Deuteromycetes）、担子菌類（Basidiomycetes）、接合菌類（Zygomycetes）に属する菌に由来する植物病害の防除に使用できる。 The agricultural and horticultural 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).

　防除の対象となる植物病害（病原菌）の例を以下に示す。
　テンサイ：褐斑病（Cercospora beticola）、黒根病（Aphanomyces cochlioides ）、根腐病（Thanatephorus cucumeris）、葉腐病（Thanatephorus cucumeris）、さび病（Uromyces betae）、うどんこ病（Oidium sp.）、斑点病（Ramularia beticola）、苗立枯病（Aphanomyces cochlioides、Pythium ultimum）など
　ラッカセイ：褐斑病（Mycosphaerella arachidis）、汚斑病（Ascochyta sp.）、さび病（Puccinia arachidis）、立枯病（Pythium debaryanum）、さび斑病（Alternaria alternata）、白絹病（Sclerotium rolfsii）黒渋病（Mycosphaerella berkeleyi）、黒根腐病（Calonectria ilicicola）など
　キュウリ：うどんこ病（Sphaerotheca fuliginea）、べと病（Pseudoperonospora cubensis）、つる枯病（Mycosphaerella melonis）、つる割病（Fusarium oxysporum）、菌核病（Sclerotinia sclerotiorum）、灰色かび病（Botrytis cinerea）、炭そ病（Colletotrichum orbiculare）、黒星病（Cladosporium cucumerinum）、褐斑病（Corynespora cassiicola）、苗立枯病（Pythium debaryanum、Rhizoctonia solani Kuhn）、ホモプシス根腐病（Phomopsis sp.）斑点細菌病（Pseudomonas syringae pv. Lachrymans）など
　トマト：灰色かび病（Botrytis cinerea）、葉かび病（Cladosporium fulvum）、疫病（Phytophthora infestans）、半身萎凋病（Verticillium albo-atrum、 Verticillium dahliae）、うどんこ病（Oidium neolycopersici）、輪紋病（Alternaria solani）、すすかび病（Pseudocercospora fuligena）、青枯病（Ralstonia solanacearum）、菌核病（Sclerotinia sclerotiorum）など
　ナス：灰色かび病（Botrytis cinerea）、黒枯病（Corynespora melongenae）、うどんこ病（Erysiphe cichoracearum）、すすかび病（Mycovellosiella nattrassii）、菌核病（Sclerotinia sclerotiorum）、半身萎凋病（Verticillium dahliae）、褐紋病（Phomopsis vexans）など
　トウガラシ：疫病（Phytophthora capsici）、灰色かび病（Botrytis cinerea）、菌核病（Sclerotinia sclerotiorum）、炭疽病（Colletotrichum aenigma、Colletotrichum capsici、Colletotrichum fructicola、 Colletotrichum jiangxiense）、うどんこ病（Leveillula taurica）など
　イチゴ：灰色かび病（Botrytis cinerea）、うどんこ病（Sphaerotheca humuli）、炭そ病（Colletotrichum acutatum、Colletotrichum fragariae）、疫病（Phytophthora cactorum）、軟腐病（Rhizopus stolonifer）、萎黄病（Fusarium oxysporum）、萎凋病（Verticillium dahliae）、菌核病（Sclerotinia sclerotiorum）など
　タマネギ：灰色腐敗病（Botrytis allii）、灰色かび病（Botrytis cinerea）、白斑葉枯病（Botrytis squamosa）、べと病（Peronospora destructor）、白色疫病（Phytophthora porri）、小菌核病（Ciborinia allii）、小菌核腐敗病（Botrytis squamosa）、乾腐病（Fusarium oxysporum）、紅色根腐病（Pyrenochaeta terrestris）、黒腐菌核病（Sclerotium cepivorum）、さび病（Puccinia allii）、白絹病（Sclerotium rolfsii）など
　ネギ：軟腐病（Pectobacterium carotovorum）、べと病（Peronospora destructor）、葉枯病（Pleospora allii）、黒腐菌核病（Sclerotium cepivorum）、さび病（Puccinia allii）、白斑葉枯病（Botrytis squamosa）、白絹病（Sclerotium rolfsii）、紅色根腐病（Pyrenochaeta terrestris）など
　キャベツ：根こぶ病（Plasmodiophora brassicae）、軟腐病（Erwinia carotovora）、黒腐病（Xanthomonas campesrtis pv. campestris）、黒斑細菌病（Pseudomonas syringae pv. maculicola、P. s. pv. alisalensis）、べと病（Peronospora parasitica）、菌核病（Sclerotinia sclerotiorum）、黒すす病（Alternaria brassicicola）、灰色かび病（Botrytis cinerea）、根朽病（Phoma lingam）、ピシウム腐敗病（Pythium aphanidermatum, Pythium ultimum）、白さび病（Albugo macrospora）など
　レタス：腐敗病（Pseudomonas cichorii, Pseudomonas marginalis）、軟腐病（Pectobacterium carotovorum）、べと病（Bremia lactucae）、灰色かび病（Botrytis cinerea）、菌核病（Sclerotinia sclerotiorum）、ビッグベイン病（Mirafiori lettuce big-vein ophiovirus）、根腐病（Fusarium oxysporum）、すそ枯病（Rhizoctonia solani）、うどんこ病（Golovinomyces orontii）など
　インゲン：菌核病（Sclerotinia sclerotiorum）、灰色かび病（Botrytis cinerea）、炭疽病（Colletotrichum lindemuthianum）、角斑病（Phaeoisariopsis griseola）など
　エンドウ：褐紋病（Mycosphaerella blight）、灰色かび病（Botrytis cinerea）、菌核病（Sclerotinia sclerotiorum）、うどんこ病（Erysiphe pisi）など Examples of plant diseases (pathogens) to be controlled are shown below.
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), etc. , 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 (Mycovellosiella nattrassii), Botrytis cinerea (Sclerotinia sclerotiorum), Botrytis cinerea (Verticillium dahliae), 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, etc. , Botrytis cinerea (Colletotrichum acutatum, Colletrichum fragariae), plague (Phytophthora cactorum), soft rot (Rhizopus stolonifer), cinerea (Fusarium oxysporum), wilt (Verticillium dahliae), Botrytis cinerea, etc. 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. Lettuce: Pseudomonas cichorii, Pseudomonas marginalis), soft rot (Pectobacterium carotovorum), cinerea (Bremia lactucae), Botrytis cinerea, sclerotinia sclerotiorum, big-vein ophiovirus, roots Sclerotinia sclerotiorum, Botrytis cinerea, etc. Ingen: Sclerotinia sclerotiorum, Botrytis cinerea, etc. ), Colletotrichum lindemuthianum, Phaeosariopsis griseola, etc. Pea: Brown spot disease (Mycosphaerella blight), Botrytis cinerea, Sclerotinia sclerotiorum, Powdery mildew (Erysiphe pisi) Such

　りんご：うどんこ病（Podosphaera leucotricha）、黒星病（Venturia inaequalis）、モニリア病（Monilinia mali）、黒点病（Mycosphaerella pomi）、腐らん病（Valsa mali）、斑点落葉病（Alternaria mali）、赤星病（Gymnosporangium yamadae）、輪紋病（Botryosphaeria berengeriana）、炭そ病（Glomerella cingulata、Colletotrichum acutatum）、褐斑病（Diplocarpon mali）、すす点病（Zygophiala jamaicensis）、すす斑病（Gloeodes pomigena）、紫紋羽病（Helicobasidium mompa）、白紋羽病（Rosellinia necatrix）、灰色かび病（Botrytis cinerea）、火傷病（Erwinia amylovora）、銀葉病（Chondrostereum purpureum）、根頭がんしゅ病（Rhizobium radiobacter 、 Rhizobium rhizogenes）など
　ウメ：黒星病（Cladosporium carpophilum）、灰色かび病（Botrytis cinerea）、灰星病（Monilinia mumecola）、すす斑病（Peltaster sp.）、ふくろ実病（Taphrina pruni）、褐色せん孔病（Phloeosporella padi）など
　カキ：うどんこ病（Phyllactinia kakicola）、炭そ病（Gloeosporium kaki）、角斑落葉病（Cercospora kaki）、円星落葉病（Mycosphaerella nawae）、灰色かび病（Botrytis cinerea）、すす点病（Zygophiala jamaicensis）など
　モモ：灰星病（Monilinia fructicola、Monilia fructigena）、黒星病（Cladosporium carpophilum）、ホモプシス腐敗病（Phomopsis sp.）、穿孔細菌病（Xanthomonas campestris pv. pruni）、縮葉病（Taphrina deformans）、炭そ病（Colletotrichum gloeosporioides）、褐色せん孔病（Phloeosporella padi）、かわらたけ病（Coriolus versicolor）など
　アーモンド：灰星病（Monilinia laxa）、斑点病（Stigmina carpophila）、黒星病（Cladosporium carpophilum）、葉ぶくれ病（Polystigma rubrum）、斑点落葉病（Alternaria alternata）、炭疽病（Colletotrichum gloeospoides）など
　オウトウ：灰星病（Monilinia fructicola）、炭そ病（Colletotrichum acutatum）、黒斑病（Alternaria sp.）、幼果菌核病（Monilinia kusanoi）、褐色せん孔病（Mycosphaerella cerasella）、うどんこ病（Podosphaera tridactyla）など
　ブドウ：灰色かび病（Botrytis cinerea）、うどんこ病（Uncinula necator）、晩腐病（Glomerella cingulata、Colletotrichum acutatum）、べと病（Plasmopara viticola）、黒とう病（Elsinoe ampelina）、褐斑病（Pseudocercospora vitis）、黒腐病（Guignardia bidwellii）、白腐病（Coniella castaneicola）、さび病（Phakopsora ampelopsidis）、白色綿雪症（病原菌未同定）、根頭がんしゅ病（Rhizobium radiobacter、Rhizobium vitis）など
　ナシ：黒星病（Venturia nashicola）、赤星病（Gymnosporangium asiaticum）、黒斑病（Alternaria kikuchiana）、輪紋病（Botryosphaeria berengeriana）、うどんこ病（Phyllactinia mali）、胴枯病（Phomopsis fukushii）、褐色斑点病（Stemphylium vesicarium）、炭そ病（Glomerella cingulata）など
　チャ：輪斑病（Pestalotiopsis longiseta、 P. theae）、炭そ病（Colletotrichum theae-sinensis）、網もち病（Exobasidium reticulatum）、赤焼病（Pseudomonas syringae）、もち病（Exobasidium vexans）など
　カンキツ：そうか病（Elsinoe fawcettii）、青かび病（Penicillium italicum）、緑かび病（Penicillium digitatum）、灰色かび病（Botrytis cinerea）、黒点病（Diaporthe citri）、かいよう病（Xanthomonas campestris pv.Citri）、うどんこ病（Oidium sp.）、疫病（Phytophthora citrophthora）、炭そ病（Colletotrichum fioriniae）など
　キウイフルーツ：花腐細菌病（Pseudomonas marginalis、Pseudomonas syringae、Pseudomonas viridiflava）、かいよう病（Pseudomonas syringae）、灰色かび病（Botrytis cinerea）、果実軟腐病（Botryosphaeria dothidea、Diaporthe sp.、Lasiodiplodia theobromae）、すす斑病（Pseudocercospora actinidiae）など
　オリーブ：炭疽病（Colletotrichum acutatum, Colletotrichum gloeosporioides）、Peacock spot（Spilocaea oleaginea）など
　クリ：炭疽病（Colletotrichum gloeosporioides）など Apples: 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) Ume: Black spot disease (Cladosporium carpophilum), Botrytis cinerea, Monilinia mumecola, Peltaster sp., Taphrina pruni, Phloeosporella padi Kaki: Udonko disease (Phyllactinia kakicola), charcoal disease (Gloeosporium kaki), keratosespora kaki, Monilinia cinerea, Botrytis cinerea, Zygophiala peaches such as jamaicensis): Botrytis cinerea (Monilinia fructicola, Monilia fructigena), Botrytis cinerea (Cladosporium carpophilum), Phomopsis sp. , Colletotrichum gloeosporioides, Phloeosporella padi, Coriolus versicolor, etc. Almonds: Monilinia laxa, Stigmina carpophila, Cladosporium carpophilum, leaf buds Polystigma rubrum, Alternaria alternata, Colletotrichum gloeospoides, etc. Outou: Monilinia fructicola, Colletotrichum acutatum, Alternaria sp., Juvenile Fruit fungus nucleus disease (Monilinia kusanoi), brown puncture disease (Mycosphaerella cerasella), udonko disease (Podosphaera tridactyla), etc. Grape: gray mold (Botrytis cinerea), udonko disease (Uncinula necator), late rot (Glomerella cingulata, Colletotrichum acutatum, Plasmopara viticola, Elsinoe ampelina, Pseudocercospora vitis, Guignardia bidwellii, Coniella castaneicola, Phakopsora ampelopsidis , White cotton scab (pathogen unidentified), root cancer radiobacter, Rhizobium vitis, etc. Pear: Black spot disease (Venturia nashicola), Gymnosporangium asiaticum, Black spot disease (Alternaria kikuchiana), Ring pattern Diseases (Botryosphaeria berengeriana), Udonko disease (Phyllactinia mali), Body blight (Phomopsis fukushii), Brown spot disease (Stemphylium vesicarium), Charcoal disease (Glomerella cingulata), etc. Cha: Pestalotiops is longiseta, P. theae), charcoal disease (Colletotrichum theae-sinensis), reticular disease (Exobasidium reticulatum), red burning disease (Pseudomonas syringae), blast disease (Exobasidium vexans), etc. , Blue mold (Penicillium italicum), Green mold (Penicillium digitatum), Gray mold (Botrytis cinerea), Black spot disease (Diaporthe citri), Canker disease (Xanthomonas campestris pv.Citri), Udonko disease (Oidium sp.), Epidemic (Phytophthora citrophthora), charcoal disease (Colletotrichum fioriniae), etc. 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.

　コムギ：うどんこ病（Blumeria graminis f.sp. tritici）、赤かび病（Gibberella zeae、Fusarium avenaceum、Fusarium culmorum、Fusarium crookwellense、Microdochium nivale）、赤さび病（Puccinia recondita）、黄さび病（Puccinia striiformis）、褐色雪腐病（Pythium iwayamai）、紅色雪腐病（Monographella nivalis）、眼紋病（Pseudocercosporella herpotrichoides）、葉枯病（Septoria tritici）、ふ枯病（Leptosphaeria nodorum）、雪腐小粒菌核病（Typhula incarnata）、雪腐大粒菌核病（Myriosclerotinia borealis）、立枯病（Gaeumannomyces graminis）、麦角病（Claviceps purpurea）、なまぐさ黒穂病（Tilletia caries）、裸黒穂病（Ustilago nuda）、いもち病（Pyricularia grisea）、Damping off（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）、Seedling blight（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）など
　オオムギ：斑葉病（Pyrenophora graminea）、網斑病（Pyrenophora teres）、雲形病（Rhynchosporium secalis）、裸黒穂病（Ustilago tritici、U.nuda）、Damping off（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）、Seedling blight（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）など
　イネ：いもち病（Pyricularia oryzae）、紋枯病（Rhizoctonia solani）、馬鹿苗病（Gibberella fujikuroi）、ごま葉枯病（Cochliobolus miyabeanus）、苗立枯病（Pythium graminicola）、白葉枯病（Xanthomonas oryzae）、苗立枯細菌病（Burkholderia plantarii）、褐条病（Acidovorax avenae）、もみ枯細菌病（Burkholderia glumae）、すじ葉枯病（Cercospora oryzae）、稲こうじ病（Ustilaginoidea virens）、褐色米（Alternaria alternata、Curvularia intermedia）、腹黒米（Alternaria padwickii）、紅変米（Epicoccum purpurascens）など
　タバコ：菌核病（Sclerotinia sclerotiorum）、うどんこ病（Erysiphe cichoracearum）、疫病（Phytophthora nicotianae）、など
　チューリップ：灰色かび病（Botrytis cinerea）、褐色斑点病（Botrytis tulipae）、葉腐病（Rhizoctonia solani）、球根腐敗病（Fusarium oxysporum）、皮腐病（Rhizoctonia solani）など
　バラ：黒星病（Diplocarpon rosae）、うどんこ病（Erysiphe simulans、Podosphaera pannosa）、灰色かび病（Botrytis cinerea）など
　キク：灰色かび病（Botrytis cinerea）、白さび病（Puccinia horiana）、べと病（Paraperonospora minor, Peronospora danica）、ピシウム立枯病（Pythium aphanidermatum、Pythium dissotocum、Pythium helicoides、Pythium oedochilum、Pythium sylvaticum）、立枯病（Rhizoctonia solani）、フザリウム立枯病（Fusarium solani）など
　ガーベラ：灰色かび病（Botrytis cinerea）、うどんこ病（Podosphaera xanthii）など
　ユリ：葉枯病（Botrytis elliptica, Pestalotiopsis sp.）、灰色かび病（Botrytis cinerea）など
　ヒマワリ：べと病（Plasmopara halstedii）、菌核病（Sclerotinia sclerotiorum）、灰色かび病（Botrytis cinerea）など
　ベントグラス：雪腐大粒菌核病（Sclerotinia borealis）、ラージパッチ（Rhizoctonia solani）、ブラウンパッチ（Rhizoctonia solani）、ダラースポット（Sclerotinia homoeocarpa）、いもち病（Pyricularia sp.）、赤焼病（Pythium aphanidermatum）、炭そ病(Colletotrichum graminicola)など
　オーチャードグラス：うどんこ病（Erysiphe graminis）など
　ダイズ：紫斑病（Cercospora kikuchii）、べと病（Peronospora manshurica）、茎疫病（Phytophthora sojae）、さび病（Phakopsora pachyrhizi）、菌核病（Sclerotinia sclerotiorum）、炭そ病（Colletotrichum truncatum）、灰色かび病（Botrytis cinerea）、黒とう病（Elsinoe glycines)、黒点病（Diaporthe phaseolorum var. sojae）、Damping off（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）、Seedling blight（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）など
　ジャガイモ：疫病（Phytophthora infestans）、夏疫病（Alternaria solani）、黒あざ病（Thanatephorus cucumeris）、半身萎凋病（Verticillium albo－atrum、V. dahliae、V. nigrescens）、黒あし病（Pectobacterium atrosepticum）、軟腐病（Pectobacterium carotovorum）、灰色かび病（Botrytis cinerea）、そうか病（Streptomyces spp.）、菌核病（Sclerotinia sclerotiorum）など
　ヤマノイモ：葉渋病（Cylindrosporium dioscoreae）、炭疽病（Colletotrichum gloeosporioides）、青かび病（Penicillium sclerotigenum）など
　サツマイモ：紫紋羽病（Helicobasidium mompa）、つる割病（Fusarium oxysporum）など
　サトイモ：疫病（Phytophthora colocasiae）、茎腐病（Rhizoctonia solani）など
　ショウガ：根茎腐敗病（Pythium ultimum、Pythium myriotylum）、白星病（Phyllosticta zingiberis）など
　バナナ：パナマ病（Fusarium oxysporum）、シガトカ病（Mycosphaerella fijiensis、M. musicola）など
　マンゴー：炭そ病（Colletotrichum aenigma）、かいよう病（Xanthomonas campestris）、軸腐病（Diaporthe pseudophoenicicola、Lasiodiplodia theobromae、Lasiodiplodia spp.、Neofusicoccum parvum、Neofusicoccum sp.）、灰色かび病（Botrytis cinerea）など
　ナタネ：菌核病（Sclerotinia sclerotiorum）、根朽病（Phoma lingam）、黒斑病（Alternaria brassicae）、うどんこ病（Erysiphe cruciferarum、Erysiphe cichoracearum、Oidium matthiolae）、べと病（Peronospora parasitica）など
　コーヒー：さび病（Hemileia vastatrix）、炭疽病（Colletotrichum coffeanum）、褐眼病（Cercospora coffeicola）など
　サトウキビ：褐さび病（Puccinia melanocephala）など
　トウモロコシ：ひょう紋病（Gloeocercospora sorghi）、さび病（Puccinia sorghi）、南方さび病（Puccinia polysora）、黒穂病（Ustilago maydis）、ごま葉枯病（Cochliobolus heterostrophus）、すす紋病（Setosphaeria turcica）、Damping off（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）、Seedling blight（Pythium spp.、Fusarium spp.、Rhizoctonia spp.）など
　ワタ：苗立枯病（Pythium sp.）、さび病（Phakopsora　gossypii）、白かび病（Mycosphaerella areola）、炭疽病（Glomerella gossypii）など
　ホップ：べと病（Pseudoperonospora humuli）、うどんこ病（Oidium sp.、Podosphaera macularis）、灰色かび病（Botrytis cinerea）など Wheat: 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 caries, Ustilago nuda, Pyricularia grisea ), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), Etc. ), Cloud-shaped disease (Rhynchosporium secalis), Naked scab (Ustilago tritici, U.nuda), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.) Rice: blast (Pyricularia oryzae), blight (Rhizoctonia solani), idiot seedling disease (Gibberella fujikuroi), sesame leaf blight (Cochliobolus miyabeanus), seedling blight (Pythium) graminicola), Botrytis cinerea (Xanthomonas oryzae), Botrytis cinerea (Burkholderia plantarii), Botrytis cinerea (Acidovorax avenae), Botrytis cinerea (Burkholderia glumae), Botrytis cinerea (Cercospora oryzae), Botrytis cinerea (Ustilaginoidea virens), Brown rice (Alternaria alternata, Curvularia intermedia), Botrytis cinerea (Alternaria padwickii), Botrytis cinerea (Epicoccum purpurascens), etc. Tobacco: 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. Disease (Peronospora manshurica), Stem plague (Phytophthora sojae), Rhizoctonia (Phakopsora pachyrhizi), Sclerotinia sclerotiorum, Collettrichum truncatum, Botrytis cinerea, Botrytis cinerea, Elsinoe ), Black spot disease (Diaporthe phaseolorum var. Sojae), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), Etc. ), Summer plague (Alternaria solani), Botrytis cinerea (Thanatephorus cucumeris), Half-body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens), Botrytis cinerea (Pectobacterium atrosepticum), Soft rot (Pectobacterium carotovorum), Botrytis cinerea, Streptomyces spp., Sclerotinia sclerotiorum, etc. Yamanoimo: Cylindr osporium dioscoreae), coal scab (Colletotrichum gloeosporioides), blue mold (Penicillium sclerotigenum), etc. Solani, 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. Sugar cane: brown sigato (Puccinia melanocephala), etc. Corn: panama disease (Gloeocercospora sorghi), rust (Puccinia sorghi), southern rust (Puccinia polysora), black ear maydis), sesame leaf blight (Cochliobolus heter) ostrophus), soot scab (Setosphaeria turcica), Damping off (Pythium spp., Fusarium spp., Rhizoctonia spp.), Seedling blight (Pythium spp., Fusarium spp., Rhizoctonia spp.), Etc. Pythium sp.), Rhizoctonia (Phakopsora gossypii), White mold (Mycosphaerella areola), Charcoal (Glomerella gossypii), etc. Hop: Sticky disease (Pseudoperonospora humuli), Udonko disease (Oidium sp., Podosphaera macularis), Gray Mold disease (Botrytis cinerea), etc.

〔施用方法・混合剤〕
　本発明の農園芸用殺菌剤は、穀物類；野菜類；根菜類；イモ類；果樹類、茶、コーヒー、カカオなどの樹木類；牧草類；芝類；ワタなどの植物に対して用いることが好ましい。 [Application method / mixture]
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.

　本発明の農園芸用殺菌剤は、植物類の各部位、たとえば、葉、茎、柄、花、蕾、果実、種子、スプラウト、根、塊茎、塊根、苗条、挿し木などに施用することができる。また、これら植物類の改良品種・変種、栽培品種、さらには突然変異体、ハイブリッド体、遺伝子組み換え体（ＧＭＯ）を対象とすることもできる。 The agricultural and horticultural 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. .. In addition, improved varieties / varieties of these plants, cultivars, mutants, hybrids, and genetically modified organisms (GMOs) can also be targeted.

　本発明の農園芸用殺菌剤は、花卉、芝、牧草を含む農園芸作物に発生する種々の病害の防除をするために行われる種子処理、茎葉散布、土壌施用、水面施用などに使用することができる。 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.

　本発明の農園芸用殺菌剤は、本発明のチエノピリミジン化合物以外の成分を含有してもよい。他の成分として、製剤化のために使用する公知の担体などを挙げることができる。また、他の成分として、従来公知の、殺菌剤、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、植物調節剤、共力剤、肥料、土壌改良剤、動物用飼料などを挙げることができる。このような他の成分を含有することによって、相乗効果を奏することがある。 The agricultural and horticultural fungicide of the present invention may contain components other than the thienopyrimidine compound of the present invention. Examples of other components include known carriers used for formulation. In addition, as other components, 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.

　本発明の農園芸用殺菌剤と混用又は併用することができる、殺菌剤の具体例を以下に示す。
（１）核酸生合成阻害剤：
　（ａ）ＲＮＡポリメラーゼＩ阻害剤：ベナラキシル、ベナラキシル－Ｍ、フララキシル、メタラキシル、メタラキシル－Ｍ；オキサジキシル；クロジラコン、オフレース；
　（ｂ）アデノシンデアミナーゼ阻害剤：ブピリメート、ジメチリモール、エチリモール；
　（ｃ）ＤＮＡ／ＲＮＡ合成阻害剤：ヒメキサゾール、オクチリノン；
　（ｄ）ＤＮＡトポイソメラーゼＩＩ阻害剤：オキソリン酸。 Specific examples of the fungicide that can be mixed or used in combination with the agricultural and horticultural fungicide of the present invention are shown below.
(1) 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.

（２）有糸核分裂阻害剤及び細胞分裂阻害剤：
　（ａ）β－チューブリン重合阻害剤：ベノミル、カルベンダジム、クロルフェナゾール、フベリダゾール、チアベンダゾール；チオファネート、チオファネートメチル；ジエトフェンカルブ；ゾキサミド；エタボキサム；
　（ｂ）細胞分裂阻害剤：ペンシクロン；
　（ｃ）スペクトリン様タンパク質の非局在化阻害剤：フルオピコリド、フルオピモミド。 (2) Mitotic and fission inhibitors:
(A) β-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.

（３）呼吸阻害剤：
　（ａ）複合体Ｉ－ＮＡＤＨ酸化還元酵素阻害剤：ジフルメトリム；トルフェンピラド；
　（ｂ）複合体II－コハク酸脱水素酵素阻害剤：ベノダニル、フルトラニル、メプロニル；イソフェタミド；フルオピラム；フェンフラム、フルメシクロックス；カルボキシン、オキシカルボキシン；チフルザミド；ベンゾビンジフルピル、ビキサフェン、フルキサピロキサド、フラメトピル、イソピラザム、ペンフルフェン、ペンチオピラド、セダキサン；ボスカリド、ピジフルメトフェン、イソフルシフラム、ピラジフルミド、インピルフルキサム(inpyrfluxam) 、ピラプロポイン（Pyrapropoyne）；
　（ｃ）複合体III－ユビキノールオキシダーゼＱｏ阻害剤：アゾキシストロビン、クモキシストロビン、クメトキシストロビン、エノキサストロビン、フルフェノキシストロビン、ピコキシストロビン、ピラオキシストロビン；ピラクロストロビン、ピラメトストロビン、トリクロピリカルブ；クレソキシム－メチル、トリフロキシストロビン；ジモキシストロビン、フェナミンストロビン、メトミノストロビン、オリサストロビン；ファモキサドン；フルオキサストロビン；フェンアミドン；ピリベンカルブ；メチルテトラプロール；マンデストロビン；
　（ｄ）複合体III－ユビキノール還元酵素Ｑｉ阻害剤：シアゾファミド；アミスルブロム；フェンピコキサミド
　（ｅ）酸化的リン酸化の脱共役剤：ビナパクリル、メプチルジノカップ、ジノカップ；フルアジナム；フェリムゾン；
　（ｆ）酸化的リン酸化阻害剤（ＡＴＰ合成酵素の阻害剤）：フェンチンアセテート、塩化フェンチン、水酸化フェンチン；
　（ｇ）ＡＴＰ生産阻害剤：シルチオファム；
　（ｈ）複合体III：チトクロームｂｃ１（ユビキノン還元酵素）のＱｘ（未知）阻害剤：アメトクトラジン。 (3) Respiratory 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, fluphenoxystrobin, picoxystrobin, pyraoxystrobin; pyracrostrobin , Pyrametostrobin, triclopyricalve; cresoxime-methyl, trifloxystrobin; dymoxystrobin, phenaminestrobin, metminostrobin, orythastrobin; famoxadon; fluoroxastrobin; fenamiden; pyribenecarb; methyltetraprol; man Destrobin;
(D) Complex III-Ubiquinol Reductase Qi Inhibitor: Siazofamide; Amisulbrom; Fempicoxamide (e) Decoupling agent for oxidative phosphorylation: Binapacryl, Meptyldinocup, Dinocup; Fluazinum; Felimzone;
(F) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(G) ATP production inhibitor: silthiofam;
(H) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): amethoctrazine.

（４）アミノ酸及びタンパク質合成阻害剤：
　（ａ）メチオニン生合成阻害剤：アンドプリム、シプロジニル、メパニピリム、ピリメタニル；
　（ｂ）タンパク質合成阻害剤：ブラストサイジン－Ｓ、カスガマイシン、カスガマイシン塩酸塩、ストレプトマイシン、オキシテトラサイクリン。 (4) Amino acid and protein synthesis inhibitors:
(A) Methionine biosynthesis inhibitors: andprim, cyprodinyl, mepanipyrim, pyrimethanyl;
(B) Protein synthesis inhibitor: Blasticidin-S, casugamycin, casugamycin hydrochloride, streptomycin, oxytetracycline.

（５）シグナル伝達阻害剤：
　（ａ）シグナル伝達阻害剤：　キノキシフェン、プロキナジド；
　（ｂ）浸透圧シグナル伝達におけるＭＡＰ・ヒスチジンキナーゼ阻害剤：フェンピクロニル、フルジオキソニル；クロゾリネート、イプロジオン、プロシミドン、ビンクロゾリン。 (5) Signal transduction inhibitor:
(A) Signal transduction inhibitors: quinoxyphen, proquinazide;
(B) MAP / histidine kinase inhibitors in osmotic signal transduction: fenpicronyl, fludioxonyl; clozolinate, iprodion, procymidone, vinclozoline.

（６）脂質及び細胞膜合成阻害剤：
　（ａ）りん脂質生合成、メチルトランスフェラーゼ阻害剤：エジフェンホス、イプロベンホス、ピラゾホス；イソプロチオラン；
　（ｂ）脂質の過酸化剤：ビフェニル、クロロネブ、ジクロラン、キントゼン、テクナゼン、トルクロホスメチル；エトリジアゾール；
　（ｃ）細胞膜に作用する剤：ヨードカルブ、プロパモカルブ、プロパモカルブ塩酸塩、プロパモカルブホセチレート、プロチオカルブ；
　（ｄ）病原菌細胞膜を撹乱する微生物：バチルスズブチリス菌、バチルスズブチリスＱＳＴ７１３株、バチルスズブチリスＦＺＢ２４株、バチルスズブチリスＭＢＩ６００株、バチルスズブチリスＤ７４７株；
　（ｅ）細胞膜を撹乱する剤：ゴセイカユプテ（ティーツリー）の抽出物。 (6) 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 Kayupte (tea tree).

（７）細胞膜のステロール生合成阻害剤：
　（ａ）ステロール生合成におけるＣ１４位の脱メチル化阻害剤：トリホリン；ピリフェノックス、ピリソキサゾール；フェナリモル、フルルプリミドール、ヌアリモル；イマザリル、イマザリル硫酸塩、オキスポコナゾール、ペフラゾエート、プロクロラズ、トリフルミゾール、ビニコナゾール；アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジクロブトラゾール、ジフェノコナゾール、ジニコナゾール、ジニコナゾール－Ｍ、エポキシコナゾール、エタコナゾール、フェンブコナゾール、フルキンコナゾール、フルシラゾール、フルトリアホール、フルコナゾール、フルコナゾール－シス、ヘキサコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブタニル、ペンコナゾール、プロピコナゾール、シメコナゾール、テブコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール；プロチオコナゾール、ボリコナゾール、メフェントリフルコナゾール；
　（ｂ）ステロール生合成におけるΔ１４還元酵素及びΔ８→Δ７－イソメラーゼの阻害剤：アルジモルフ、ドデモルフ、ドデモルフ酢酸塩、フェンプロピモルフ、トリデモルフ；フェンプロピジン、ピペラリン；スピロキサミン；
　（ｃ）ステロール生合成系のＣ４位脱メチル化における３－ケト還元酵素阻害剤：フェンヘキサミド；フェンピラザミン；
　（ｄ）ステロール生合成系のスクワレンエポキシダーゼ阻害剤：ピリブチカルブ；ナフチフィン、テルビナフィン。 (7) Cell membrane sterol biosynthesis 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, simeconazole, tebuconazole, tetraconazole, triazimefone, triazimenol, triticonazole; prothioconazole, voriconazole, mephen Trifluconazole;
(B) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperarin; spiroxamine;
(C) 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis system: fenhexamide; fenpyrazamine;
(D) Squalene epoxidease inhibitor of sterol biosynthesis system: pyribuchicarb; naftifine, terbinafine.

（８）細胞壁合成阻害剤：
　（ａ）トレハラーゼ阻害剤：バリダマイシン；
　（ｂ）キチン合成酵素阻害剤：ポリオキシン、ポリオクソリム；
　（ｃ）セルロース合成酵素阻害剤：ジメトモルフ、フルモルフ、ピリモルフ；ベンチアバリカルブ、イプロバリカルブ、バリフェナレート；マンジプロパミド。 (8) Cell wall synthesis inhibitor:
(A) Trehalase inhibitor: validamycin;
(B) Chitin synthase inhibitors: polyoxine, polyoxolim;
(C) Cellulose Synthetic Enzyme Inhibitors: Dimethmorph, Fulmorph, Pyrimorph; Bench Avaricarb, Iprovaricarb, Variphenalate; Mandipropamide.

（９）メラニン生合成阻害剤
　（ａ）メラニン生合成の還元酵素阻害剤：フサライド；ピロキロン；トリシクラゾール；
　（ｂ）メラニン生合成の脱水酵素阻害剤：カルプロパミド；ジクロシメット；フェノキサニル；
　（ｃ）メラニン生合成のポリケタイド合成阻害剤：トルプロカルブ。 (9) Melanin biosynthesis 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.

（１０）宿主植物の抵抗性誘導剤：
　（ａ）サリチル酸合成経路に作用する剤：アシベンゾラル－Ｓ－メチル；
　（ｂ）その他：プロベナゾール、チアジニル、イソチアニル、ジクロベンチアゾクス、イプフェントリフルコナゾール、ラミナリン、オオイタドリ抽出液。 (10) Host plant resistance inducer:
(A) Agent acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(B) Others: probenazole, thiazinyl, isothianil, diclobenazox, ipfentrifluconazole, laminarin, Reynoutria sachalinensis extract.

（１１）作用性が不明な剤：シモキサニル、ホセチルアルミニウム、リン酸（リン酸塩）、テクロフタラム、トリアゾキシド、フルスルファミド、ジクロメジン、メタスルホカルブ、シフルフェナミド、メトラフェノン、ピリオフェノン、ドジン、ドジン遊離塩基、フルチアニル。 (11) Agents of unknown activity: simoxanyl, Josetylaluminum, phosphate (phosphate), tecrophthalam, triazoxide, flusulfamide, dichromedin, metasulfocarb, ciflufenamide, metrafenone, pyriophenone, dodine, dodine free base, fluthianyl.

（１２）多作用点を有する剤：銅（銅塩）、ボルドー液、水酸化銅、銅ナフタレート、酸化銅、オキシ塩化銅、硫酸銅、硫黄、硫黄製品、多硫化カルシウム；ファーバム、マンコゼブ、マネブ、マンカッパー、メチラム、ポリカーバメート、プロピネブ、チラム、ジネブ、ジラム；キャプタン、カプタホール、フォルペット；クロロタロニル；ジクロフルアニド、トリルフルアニド；グアザチン、グアザチンアセテート、イミノクタジン酢酸塩（iminoctadine triacetate）、イミノクタジンアルベシル酸塩（iminoctadine trialbesilate）；アニラジン；ジチアノン；キノメチオネート；フルオルイミド。 (12) Agents 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.

（１３）その他の剤：　ＤＢＥＤＣ、フルオロフォルペット、ビス（８－キノリノラト）銅（II）、プロパミジン、クロロピクリン、シプロフラム、アグロバクテリウム、ベトキサジン、ジフェニルアミン、メチルイソチアネート（ＭＩＴＣ）、ミルデオマイシン、カプサイシン、クフラネブ、シプロスルファミド、デバカルブ、ジクロロフェン、ジフェンゾクワット、ジフェンゾクワットメチルスルホネート、フルメトベル、ホセチルカルシウム、ホセチルナトリウム、イルママイシン、ナタマイシン、ニトロタールイソプロピル、オキサモカルブ、ピロールニトリン、テブフロキン、トルニファニド、ザリラミド、アルゴフェーズ（Algophase）、アミカルチアゾール（Amicarthiazol）、オキサチアピプロリン（Oxathiapiprolin）、フルオキサピプロリン（Fluoxapiprolin）、メチラム亜鉛、ベンチアゾール、トリクラミド、ユニコナゾール、オキシフェンチイン（Oxyfenthiin）、ピカルブトラゾクス（Picarbutrazox）、キノフメリン（Quinofumelin）、フロリルピコキサミド（Florylpicoxamid）、フルインダピル（Fluindapyr）、アミノピリフェン（Aminopyrifen）、ピリダクロメチル（Pyridachlomethyl）、イプフルフェノキン（Ipflufenoquin）、ジピメチトロン（Dipymetitrone）。 (13) Other agents: DBEDC, fluorofolpet, bis (8-quinolinolato) copper (II), propamidin, chloropyrrolnitrin, cyprofulum, agrobacterium, betoxazine, diphenylamine, methylisothianate (MITC), mildeomycin , Capsaicin, Kufraneb, Ciprosulfamide, Devacarb, Dichlorophen, Diphenzoquat, Diphenzoquat Methylsulfonate, Flumethbel, Josetylcalcium, Josetilsodium, Irumamycin, Natamicin, Nitrotalisopropyl, Oxamocarb, Pyrrolnitrin, Tebflokin, tornifanide, zariramid, algophase, Amicarthiazol, Oxathiapiprolin, Fluoxapiprolin, methylamzinc, benchazole, tricramide, uniconazole, oxyfenthiin ), Picarbutrazox, Quinofumelin, Florylpicoxamid, Fluindapyr, Aminopyrifen, Pyridachlomethyl, Ipflufenoquin , Dipymetitrone.

　本発明の農園芸用殺菌剤と混用又は併用することができる、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤、駆虫剤などの具体例を以下に示す。 Specific examples of 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.

（１）アセチルコリンエステラーゼ（AChE）阻害剤（カーバメート系）：
　（１Ａ）アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、ブトカルボキシム、ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フェノブカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メチオカルブ、メソミル、メトルカルブ、オキサミル、ピリミカーブ、プロポキスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、ＸＭＣ、キシリルカルブ；ＭＩＰＣ、ＭＰＭＣ、ＭＴＭＣ；アルドキシカルブ、アリキシカルブ、アミノカルブ、ブフェンカルブ、クロエトカルブ、フェノチオカルブ、プロメカルブ。 (1) 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.

　（１Ｂ）アセチルコリンエステラーゼ（AChE）阻害剤（有機リン系）：　アセフェート、アザメチホス、アジンホスエチル、アジンホスメチル、カズサホス、クロレトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホスメチル、クマホス、シアノホス、ジメトン-S-メチル、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジメチルビンホス、ジスルホトン、ＥＰＮ、エチオン、エトプロホス、ファンフル、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イミシアホス、イソフェンホス、イソプロピル=O-(メトキシアミノチオホスホリル)サリチラート、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレッド、オメトエート、オキシジメトンメチル、パラチオン、パラチオンメチル、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホスメチル、プロフェノホス、プロペタムホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリムホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン；ブロモホス・エチル、ＢＲＰ、カルボフェノチオン、シアノフェンホス、ＣＹＡＰ、デメトン－Ｓ－メチルスルホン、ジアリホス、ジクロフェンチオン、ジオキサベンゾホス、エトリムホス、フェンスルホチオン、フルピラゾホス、ホノホス、ホルモチオン、ホスメチラン、イサゾホス、ヨードフェンホス、メタクリホス、ピリミホスエチル、ホスホカルブ、プロパホス、プロトエート、スルプロホス。 (1B) Acetylcholinesterase (AChE) inhibitor (organophosphorus): acephate, azamethifos, azinephosethyl, azinephosmethyl, cassaphos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifosmethyl, bearphos, cyanophos, dimethoate-S-methyl, Diazinone, dichlorpyrifos, dichlorpyrifos, dimethoate, dimethylbinphos, disulfoton, EPN, etion, etoplophos, funful, phenamiphos, fenitrothione, fention, hostiazeto, heptenophos, imiciaphos, isophenphos, isopropyl = O- (methoxyaminothiophosphoryl) salicylate, isoxa , Malathion, Mecarbam, Metamidphos, Metidathione, Mevinphos, Monochrometophos, Nared, Ometoate, Oxydimethoate, Palatin, Palatinmethyl, Fentate, Holate, Hosalon, Hosmet, Phosphamiden, Hoxim, Pyrimiphosmethyl, Profenophos, Propetamphos, Prothiophos , Kinalphos, Sulfotep, Tebupyrimphos, Temefos, Telbuphos, Tetrachlorpyrifos, Thiometon, Triazophos, Trichlorfon, Bamidthione; , Dioxabenzophos, etrimphos, phensulfosone, flupyrazophos, honophos, formotione, phosmethyran, isazophos, iodophenphos, methaphos, pyrimiphosethyl, phosphocarb, propaphos, protoate, sulprophos.

（２）GABA作動性塩化物イオン(塩素イオン)チャネルブロッカー：アセトプロール、クロルデン、エンドスルファン、エチプロール、フィプロニル、ピラフルプロール、ピリプロール、カンフェクロル、ヘプタクロル、ジエノクロル、フルフィプロル。
（３Ａ）ナトリウムチャネルモジュレーター（ピレスロイド系）：アクリナトリン、アレスリン、d-シス-トランス-アレスリン、d-トランス-アレスリン、ビフェントリン、ビオアレスリン、ビオアレスリン-S-シクロペンテニル-異性体、ビオレスメトリン、シクロプロトリン、シフルトリン、β-シフルトリン、シハロトリン、λ-シハロトリン、γ-シハロトリン、シペルメトリン、α-シペルメトリン、β-シペルメトリン、θ-シペルメトリン、ζ-シペルメトリン、シフェノトリン[(1R)-トランス異性体]、デルタメトリン、エンペントリン[(EZ)-(1R)-異性体]、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、τ-フルバリネート、ハルフェンプロックス、イミプロトリン、カデスリン、ペルメトリン、フェノトリン[(1R)-トランス異性体]、プラレトリン、ピレトリン、レスメトリン、シラフルオフェン、テフルトリン、テトラメスリン、テトラメスリン[(1R)-異性体]、トラロメトリン、トランスフルトリン。
　κ-ビフェントリン、ビオペルメトリン、クロロプラレスルン、ジメフルトリン、フェンフルトリン、フェンピリトリン、フルフェンプロックス、ヘプタフルスリン、メペルフルスリン、ε-メトフルトリン、モンフルオロトリン、ε-モンフルオロトリン、トランスペルメトリン、プロフルトリン、プロトリフェンブト、κ-テフルトリン、テラレトリン、テトラメチルフルスリン；ビオエタノメトリン。
（３Ｂ）ナトリウムチャネルモジュレーター（ＤＤＴ類）：
　ＤＤＴ、メトキシクロル。 (2) GABAergic chloride ion (chlorine ion) channel blocker: acetoprol, chlordane, endosulfan, ethiprol, fipronil, pilafrol, piriprol, campechlor, heptachlor, dienochlor, fulfiprol.
(3A) Sodium channel modulator (pyrethroid): acrinathrin, allethrin, d-cyste-trans-allethrin, d-trans-allethrin, bifentrin, bioallethrin, bioallethrin-S-cyclopentenyl-isomer, bioresmethrin, cycloprothrin , Cypermethrin, β-cypermethrin, cypermethrin, λ-cypermethrin, γ-cypermethrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, ciphenotrin [(1R) -trans isomer ], Deltamethrin, Empentrin [(EZ)-(1R) -isomer], esphenvalerate, etofenprox, phenpropatrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halphenprox, imiprothrin, Cadethrin, permethrin, phenotrin [(1R) -trans isomer], prarethrin, pyrethrin, allethrin, cypermethrin, tefluthrin, tetramesrin, tetramesrin [(1R) -isomer], tralomethrin, transfluthrin.
κ-Bifentrin, biopermethrin, chloropralesrun, dimefluthrin, fenfluthrin, fenpyritrin, flufenprox, heptafluthrin, mepermethrin, ε-methfurthrin, monfluorothrin, ε-monfluorothrin, transpermethrin, profluthrin Protrifenbut, κ-tefluthrin, terraretrin, tetramethylfluthrin; bioetanomethrin.
(3B) Sodium channel modulators (DDTs):
DDT, methoxychlor.

（４）ニコチン性アセチルコリン受容体アゴニスト(nAChR)競合的モジュレーター：：アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、ニチアジン、チアクロプリド、チアメトキサム、スルホキサフロル、ニコチン、フルピラジフロン、トリフルメゾピリム。
ジクロロメゾチアズ、フルピリミン。
（５）ニコチン性アセチルコリン受容体(nAChR)アロステリックモジュレーター：スピネトラム、スピノサド。
（６）グルタミン酸作動性塩化物イオン(塩素イオン)チャネル(GluCl) アロステリックモジュレーター：アバメクチン、エマメクチン、エマメクチン安息香酸塩、レピメクチン、ミルベメクチン；イベルメクチン、セラメクチン、ドラメクチン、エプリノメクチン、モキシデクチン、ミルベマイシン、ミルベマイシンオキシム、ネマデクチン。
（７）幼若ホルモン類似剤：ヒドロプレン、キノプレン、メトプレン、フェノキシカルブ、ピリプロキシフェン；ジオフェノラン、エポフェノナン、トリプレン。
（８）その他の非特異的(マルチサイト)阻害剤：臭化メチル、ハロゲン化アルキル類；クロルピクリン、弗化アルミニウムナトリウム、フッ化スルフリル；ホウ砂、吐酒石；オクタホウ酸ニナトリウム塩、ホウ酸ナトリウム塩、メタホウ酸ナトリウム塩；ダゾメット、メタム、メタムカリウム塩、メタムナトリウム塩。
（９）弦音器官TRPVチャネルモジュレーター：ピメトロジン、ピリフルキナゾン；アフィドピロペン。 (4) Nicotinic acetylcholine receptor agonist (nAChR) Competitive modulator :: Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nitenpyram, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyraziflon, triflumesopirim.
Dichloromethane, flupyrimin.
(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulator: spinetram, spinosad.
(6) Glutamicic acid-operated chloride ion (chlorine ion) channel (GluCl) Allosteric modulators: abamectin, emamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, dramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadecin.
(7) Juvenile hormone analogs: hydroprene, quinoprene, methoprene, phenoxycarb, pyriproxyfen; diophenolan, epophenonan, triprene.
(8) Other 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.
(9) String organ TRPV channel modulator: Pymetrodin, pyrifluquinazone; Afidopyropen.

（１０）ダニ類成長阻害剤：クロフェンテジン、ジフロビダジン、ヘキシチアゾクス、エトキサゾール。
（１１）微生物由来昆虫中腸内膜破壊剤：B.t. subsp. israelensis、B.t. subsp. aizawai、B.t. subsp. kurstaki、B.t. subsp. tenebrionis；B.t.作物に含まれるタンパク質：Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1；Bacillus sphaericus。
（１２）ミトコンドリアＡＴＰ合成酵素阻害剤：ジアフェンチウロン；アゾシクロチン、シヘキサチン、酸化フェンブタスズ；プロパルギット；テトラジホン。
（１３）プロトン勾配を撹乱する酸化的リン酸化脱共役剤：クロルフェナピル、スルフルラミド、ＤＮＯＣ、ビナパクリル、ジノブトン、ジノカップ。
（１４）ニコチン性アセチルコリン受容体(nAChR)チャネルブロッカー：ベンスルタップ、カルタップ塩酸塩；ネライストキシン；チオスルタップ一ナトリウム塩、チオシクラム。
（１５）キチン生合成阻害剤　タイプ０：ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、トリフルムロン、フルアズロン。
（１６）キチン生合成阻害剤、タイプ１：ブプロフェジン、
（１７）脱皮阻害剤：シロマジン。
（１８）脱皮ホルモン(エクダイソン)受容体アゴニスト：クロマフェノジド、ハロフェノジド、メトキシフェノジド、テブフェノジド。
（１９）オクトパミン受容体アゴニスト：アミトラズ、クロルジメホルム。
（２０）ミトコンドリア電子伝達系複合体III阻害剤：アセキノシル、フルアクリピリム、ヒドラメチルノン；ビフェナゼート。
（２１）ミトコンドリア電子伝達系複合体Ｉ阻害剤(METI)：フェナザキン、フェンピロキシメート、ピリミジフェン、ピリダベン、テブフェンピラド、トルフェンピラド、ロテノン。 (10) Tick growth inhibitors: clofentezine, difluorovidazine, hexitiazox, etoxazole.
(11) 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.
(12) Mitochondrial ATP synthase inhibitor: diafentiurone; azocyclotin, cyhexatin, fenbutatin oxide; propargite; tetradiphon.
(13) Oxidative phosphorylation decoupling agent that disturbs the proton gradient: chlorfenapyr, sulfuramide, DNOC, binapacryl, dinobutone, dinocup.
(14) Nicotinic Acetylcholine Receptor (nAChR) Channel Blocker: Bensultap, Cartap Hydrochloride; Nelystoxin; Thiosultap Monosodium Salt, Thiocyclum.
(15) Chitin biosynthesis inhibitor Type 0: bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflubenzuron, fluazuron.
(16) Chitin biosynthesis inhibitor, type 1: buprofezin,
(17) Moulting inhibitor: cyromazine.
(18) Molting hormone (ecdysone) receptor agonists: chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
(19) Octopamine receptor agonists: Amitraz, Chlordimeform.
(20) Mitochondrial electron transport chain complex III inhibitor: acequinosyl, fluacripirim, hydramethylnon; biphenazate.
(21) Mitochondrial electron transport chain complex I inhibitor (METI): phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, rotenone.

（２２）電位依存性ナトリウムチャネルブロッカー：インドキサカルブ；メタフルミゾン。
（２３）アセチルＣｏＡカルボキシラーゼ阻害剤：スピロジクロフェン、スピロメシフェン、スピロテトラマト。
（２４）ミトコンドリア電子伝達系複合体IV阻害剤：リン化アルミニウム、リン化カルシウム、シアン化ナトリウム、シアン化カリウム、シアニド、ホスフィン、リン化亜鉛、。
（２５）ミトコンドリア電子伝達系複合体II阻害剤：シエノピラフェン、シフルメトフェン；ピフルブミド。
（２６）リアノジン受容体モジュレーター：クロラントラニリプロール、シアントラニプロール、フルベンジアミド、シクラニリプロール。
シハロジアミド、テトラクロラントラニリプロール、テトラニリプロール。
（２７）弦音器官モジュレーター 標的部位未特定：
　フロニカミド。
（２８）ＧＡＢＡ作動性塩化物イオン(塩素イオン)チャネルアロステリックモジュレーター：
　ブロフラニリド、フルキサメタミド。
　イソシクロセラム；アフォキソラネル、フルララネル、ロチネラル、サロラネル。
その他の殺虫剤、殺ダニ剤：
ピペロニルブトキシド、アザジラクチン、ベンゾキシメート、ブロモプロピレート、キノメチオネート、ジコホル、石灰硫黄合剤、マンコゼブ、ピリダリル、硫黄。
アシノナピル、ベンズピリモキサン、フロメトキン、フルヘキサホン、オキサゾスルフィル、チクロピラゾフロル。アミドフルメット、ジシクラニル、フェノキサクリム、フェントリファニル、フルベンジミン、メトキサジアゾン、テトラスル、トリアラセン。
ベンクロチアズ、１，３－ジクロロプロペン、ＤＣＩＰ、フェニソブロモレート、ベンゾメート、メタアルデヒド、クロルベンジレート、クロチアゾベン、フルフェナジン、ゴシップルア、ジャポニルア、石油、オレイン酸カリウム、フルエンスルフォン、トラロピリル、メチルネオデカンアミド、５－[５－(３，５－ジクロロフェニル)－５－トリフルオロメチル－４，５－ジヒドロイソオキサゾール－３－イル]－２－(１Ｈ－１，２，４－トリアゾール－１－イル)ベンゾニトリル(CAS:943137-49-3)。　 (22) Voltage-gated sodium channel blocker: indoxacarb; metaflumison.
(23) Acetyl-CoA carboxylase inhibitor: spirodiclophen, spiromesiphen, spirotetramato.
(24) Mitochondrial electron transport chain complex IV inhibitor: aluminum phosphide, calcium phosphide, sodium cyanide, potassium cyanide, cyanide, phosphine, zinc phosphide ,.
(25) Mitochondrial electron transport chain complex II inhibitor: sienopyraphen, siflumethofen; pifrubmid.
(26) Ryanodine receptor modulators: chloranthraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole.
Cyantraniliprole, tetrachlorantraniliprole, tetraniliprole.
(27) String organ modulator Target site unspecified:
Fronikamid.
(28) GABAergic Chloride Ion (Chlorine Ion) Channel Allosteric Modulator:
Brofuranilide, fluxametamid.
Isocycloserum; afoxolanel, full laranel, rotineral, salolanel.
Other insecticides, acaricides:
Piperonyl butoxide, azadirachtin, benzoximate, bromopropirate, quinomethionate, dicofol, lime sulfur, mancozeb, pyridalyl, sulfur.
Asinonapill, benzpyrimoxane, fromotkin, fullhexafone, oxadiazolefil, cyclamate pyrazoflor. Amidoflumet, disicranyl, phenoxacrim, fentrifanyl, flubenzimine, metoxadiazone, tetrasul, triarasen.
Bencrothias, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorbenzylate, clothiazoben, flufenazine, gossiplua, japonilua, petroleum, potassium oleate, fluensulphon, traropyryl, methylneodecanamide, 5 -[5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazole-3-yl] -2- (1H-1,2,4-triazole-1-yl) benzonitrile (CAS: 943137-49-3).

（２９）駆虫剤：
　（ａ）ベンズイミダゾール系：フェンベンダゾール、アルベンダゾール、トリクラベンダゾール、オキシベンダゾール、メベンダゾール、オクスフェンダゾール、パーベンダゾール、フルベンダゾール；フェバンテル、ネトビミン、チオファネート；チアベンダゾール、カンベンダゾール；
　（ｂ）サリチルアニリド系：クロサンテル、オキシクロザニド、ラフォキサニド、ニクロサミド；
　（ｃ）置換フェノール系：ニトロキシニル、ニトロスカネート；
　（ｄ）ピリミジン系：ピランテル、モランテル；
　（ｅ）イミダゾチアゾール系：レバミソール、テトラミソール；
　（ｆ）テトラヒドロピリミジン系：プラジカンテル、エプシプランテル；
　（ｇ）その他の駆虫薬：シクロジエン、リアニア、クロルスロン、メトロニダゾール、デミジトラズ；ピペラジン、ジエチルカルバマジン、ジクロロフェン、モネパンテル、トリベンジミジン、アミダンテル；チアセタルサミド、メラルサミン、アルセナマイド。 (29) 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, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetalsamide, meralsamine, arsenamide.

　本発明の農園芸用殺菌剤と混用又は併用することができる、植物調節剤の具体例を以下に示す。
　アブシジン酸、カイネチン、ベンジルアミノプリン、１，３－ジフェニルウレア、ホルクロルフェヌロン、チジアズロン、クロルフェヌロン、ジヒドロゼアチン、ジベレリンＡ、ジベレリンＡ４、ジベレリンＡ７、ジベレリンＡ３、１－メチルシクロプロパン、Ｎ－アセチルアミノエトキシビニルグリシン(別名：アビグリシン)、アミノオキシ酢酸、硝酸銀、塩化コバルト、ＩＡＡ、４－ＣＰＡ、クロプロップ、２，４－Ｄ、ＭＣＰＢ、インドール－３－酪酸、ジクロルプロップ、フェノチオール、１－ナフチルアセトアミド、エチクロゼート、クロキシホナック、マレイン酸ヒドラジド、２，３，５－トリヨード安息香酸、サリチル酸、サリチル酸メチル、（－）－ジャスモン酸、ジャスモン酸メチル、（＋）－ストリゴール、（＋）－デオキシストリゴール、（＋）－オロバンコール、（＋）－ソルゴラクトン、４－オキソ－４－（２－フェニルエチル）アミノ酪酸；エテホン、クロルメコート、メピコートクロリド、ベンジルアデニン、５－アミノレブリン酸。 Specific examples of plant growth regulators that can be mixed or used in combination with the agricultural and horticultural fungicides of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorphenurone, tidiazulone, chlorphenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abscisic acid), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloxyp, 2,4-D, MCPB, indol-3-butyric acid, gibberellin, phenothiol, 1 -Naphtylacetamide, ethicrozeto, cloxyfonac, hydrazide maleate, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonate, methyl jasmonate, (+)-strigol, (+) -Deoxystrigor, (+)-Orovancol, (+)-Solgolactone, 4-oxo-4- (2-phenylethyl) aminobutyric acid; etephon, cloxyfonac, mepicote chloride, benzyladenin, 5-aminoleverellin.

〔製剤処方〕
　本発明の農園芸用殺菌剤は、剤形によって特に限定されない。たとえば、水和剤、乳剤、粉剤、粒剤、水溶剤、懸濁剤、顆粒水和剤、錠剤などの剤形を挙げることができる。製剤への調製方法は、特に制限されず、剤形に応じて公知の調製方法を採用することができる。 [Pharmaceutical prescription]
The agricultural and horticultural fungicide of the present invention is not particularly limited depending on the dosage form. For example, 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.

　以下に、製剤実施例を若干示す。なお、以下に示す製剤処方は単なる例示であり、本発明の主旨に反しない範囲で修正することができ、本発明は以下の製剤実施例によって何ら制限されるものではない。「部」は特段の断りが無い限り「質量部」を意味する。 The following are some examples of the formulation. It should be noted that the pharmaceutical formulation shown below is merely an example and can be modified without contrary to the gist of the present invention, and the present invention is not limited by the following pharmaceutical examples. "Part" means "part by mass" unless otherwise specified.

　（製剤例１：水和剤）
　本発明のチエノピリミジン化合物４０部、珪藻土５３部、高級アルコール硫酸エステル４部及びアルキルナフタレンスルホン酸塩３部を均一に混合して微細に粉砕して、有効成分４０％の水和剤を得る。 (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.

　（製剤例２：乳剤）
　本発明のチエノピリミジン化合物３０部、キシレン３３部、ジメチルホルムアミド３０部及びポリオキシエチレンアルキルアリルエーテル７部を混合し溶解させて、有効成分３０％の乳剤を得る。 (Formation example 2: emulsion)
30 parts of the thienopyrimidine compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

　（製剤例３：粒剤）
　本発明のチエノピリミジン化合物５部、タルク４０部、クレー３８部、ベントナイト１０部及びアルキル硫酸ソーダ７部を均一に混合し、微細に粉砕し、その後、粒子直径０．５～１．０ｍｍに造粒して有効成分５％の粒剤を得る。 (Pharmaceutical example 3: Granules)
5 parts of the thienopyrimidine compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite and 7 parts of sodium alkyl sulfate are uniformly mixed, finely pulverized, and then formed into a particle diameter of 0.5 to 1.0 mm. Granulate to obtain 5% active ingredient granules.

　（製剤例４：粒剤）
　本発明のチエノピリミジン化合物５部、クレー７３部、ベントナイト２０部、ジオクチルスルホサクシネートナトリウム塩１部及びリン酸カリウム１部を均一に混合し、粉砕した。これに水を加えてよく練り合せ、その後、造粒し、乾燥させて、有効成分５％の粒剤を得る。 (Formation example 4: granules)
5 parts of the thienopyrimidine compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctyl sulfosuccinate and 1 part of potassium phosphate were uniformly mixed and pulverized. Water is added to this and kneaded well, then granulated and dried to obtain granules having 5% of the active ingredient.

　（製剤例５：懸濁剤）
　本発明のチエノピリミジン化合物１０部、ポリオキシエチレンアルキルアリルエーテル４部、ポリカルボン酸ナトリウム塩２部、グリセリン１０部、キサンタンガム０．２部及び水７３．８部を混合し、粒度が３ミクロン以下になるまで湿式粉砕し、有効成分１０％の懸濁剤を得る。 (Formation Example 5: Suspension)
10 parts of thienopyrimidine compound of the present invention, 4 parts of polyoxyethylene alkylallyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum and 73.8 parts of water are mixed, and the particle size is 3 microns or less. Wet grind to obtain a suspension of 10% active ingredient.

　（製剤例６：顆粒水和剤）
　本発明のチエノピリミジン化合物４０部、クレー３６部、塩化カリウム１０部、アルキルベンゼンスルホン酸ナトリウム塩１部、リグニンスルホン酸ナトリウム塩８部及びアルキルベンゼンスルホン酸ナトリウム塩のホルムアルデヒド縮合物５部を均一に混合して微細に粉砕後、適量の水を加えてから練り込んで粘土状にする。粘土状物を造粒し、次いで乾燥させて有効成分４０％の顆粒水和剤を得る。 (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.

〔医療用・動物用（獣医療用）抗真菌剤〕
　本発明のチエノピリミジン化合物は、人又は動物に感染する有害な病原菌、特に真菌を防除対象とした予防薬、治療薬として用いることができる。
　本発明の医療用・動物用抗真菌剤は、化合物（I）及び化合物（II）で表される化合物又はその塩から選ばれる少なくともひとつを有効成分として含有するものである。本発明の医療用抗真菌剤に含まれる化合物（I）及び化合物（II）で表される化合物又はその塩の量は、抗真菌効果を示す限りにおいて特に制限されない。 [Medical / animal (veterinary) antifungal agents]
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.

　本明細書における「動物」とは、愛玩動物や家畜・家禽、動物園や水族館等で飼育される展示動物、捕獲した野生動物、さらには研究・実験動物等の脊椎動物（ V e r t e b r a t a） を意味する。 The term "animal" as used herein refers to 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).

　例えば、以下の動物が挙げられるが、動物の具体例はこれらのみに限定されるものではない。
　ヒツジ、ヤギ、ブタ、ウマ、ウシ、スイギュウ、ロバ、ラバ、ラクダ、ラマ、アルパカ、イノシシ、トナカイ、シカ、ミンク、ゾウ、クマ、カンガルー、キツネ、イヌ、ネコ、リス、ウサギ、マウス、ラット、モルモット、ハムスター、サル、フェレット等の哺乳類。
　ハト、インコ、オウム、ブンチョウ、ジュウシマツ、カナリア、ニワトリ、アヒル、シチメンチョウ、カモ、キジ、クジャク、ダチョウ、ハクチョウ、スズメ、ウズラ、フクロウ、ワシ、タカ、ウミウなどの鳥類。
　カメレオン、イグアナ、トカゲ、ヘビ、カメ、ワニ、ヤモリなどの爬虫類。
　カエル、イモリなどの両生類。
　コイ、キンギョ、メダカ、熱帯魚、ブリ・ハマチ、タイ、カンパチ、サケ、サバ、スズキ、クエ、マグロ、アジ、ヒラメ、フグなどの魚類。 For example, the following 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 ferrets.
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.

　本発明の医療用・動物用抗真菌剤の適用が可能な病原菌として、真菌（カビ）の例を以下に示す。なお、具体例はこれらのみに限定されるものではない。
　例えば、absidia corymbiferaなどのAbsidia属；Acremonium属；Alternaria alternataなどのAlternaria属；Aspergillus flavus、Aspergillus fumigatus、Aspergillus nidulans、Aspergillus niger、Aspergillus parasiticus、Aspergillus terreusなどのAspergillus属；Bipolaris属；Blastomyces dermatitidis などのBlastomyces属；Blumeria graminis などのBlumeria属；Candida albicans、Candida glabrata、Candida krusei、Candida parapsilosis、Candida tropicalis などのCandida属；Cladosporium cladosporoides、Cladosporium herbarium などのCladosporium属；Coccidioides immitis、Coccidioides posadasii などのCoccidioides属；Colletotrichium trifolii などのColletotrichium属；Cryptococcus neoformans などのCryptococcus属；Curvularia lunata などのCurvularia属；Encephalitozoon cuniculiなどのEncephalitozoon属；Epicoccum nigrum などのEpicoccum属；Epidermophyton floccosum などのEpidermophyton属；Exophiala属；　Exserohilum rostratum などのExserohilum属；Fusarium graminarium、Fusarium solani、Fusarium sporotrichoides などのFusarium属；Fonsecaea monophora　などのFonsecaea属；　Histoplasma capsulatumなどのHistoplasma属；Leptosphaeria nodorumなどのLeptosphaeria属；　Malassezia globosa　などのMalassezia 属； Microsporum canis などのMicrosporum属；Mycosphaerella graminicolaなどのMycosphaerella属；Neurospora属；Paecilomyces lilanicus、Paecilomyces varioti などのPaecilomyces属；Penicillium chrysogenumなどのPenicillium属；　Phytophthora capsici、Phytophthora infestansなどのPhytophthora属；Plasmopara viticola などのPlasmopara属；Pneumocystis jiroveciiなどのPneumocystis属；Pyricularia oryzaeなどのPyricularia属；Pythium ultimumなどのPythium属；Puccinia coronata、Puccinia graminis などのPuccinia属；Rhizoctonia solaniなどのRhizoctonia属；Rhizomucor属；Fusarium apiospermum、Scedosporium prolificansなどのScedosporium属；Scopulariopsis brevicaulisなどのScopulariopsis属； Sporothrix schenckii　などのSporothrix 属；　Talaromyces marneffeiなどのTalaromyces属、Trichophyton mentagrophytes、Trichophyton interdigitale、Trichophyton rubrum、Trichophyton tonsurans、Trichophyton verrucosumなどのTrichophyton属；Trichosporon asahii、Trichosporon beigeliiなどのTrichosporon属；Ustilago属など。
　これらの中、本発明の抗真菌剤は、Aspergillus属、Trichophyton属又はCandida属に対して好適であり、Aspergillus fumigatus又はTrichophyton tonsuransに対して特に好適である。 An example of a fungus (mold) 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.
For example, 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. Aspergillus genus; Cryptococcus genus such as Cryptococcus neoformans; Curvularia genus such as Curvularia lunata; Encephalitozoon genus such as Encephalitozoon cuniculi; Epicocum genus such as Epicoccum nigrum; Fusarium genus such as graminarium, Fusarium solani, Fusarium sporotrichoides; Fonsecaea genus such as Fonsecaea monophora; Histoplasma genus such as Histoplasma capsulatum; Leptos such as Leptosphaeria nodorum phaeria; Malassezia genus such as Malassezia globosa; Microsporum genus such as Microsporum canis; Mycosphaerella genus such as Mycosphaerella graminicola; Neurospora genus; Paecilomyces genus such as Paecilomyces lilanicus, Paecilomyces varioti; Phytophthora genus; Plasmopara genus such as Plasmopara viticola; Pneumocystis genus such as Pneumocystis jirovecii; Pyricularia genus such as Pyricularia oryzae; Pythium genus such as Pythium ultimum; Puccinia coronata, Puccinia graminis etc. Genus; Genus Scedosporium such as Fusarium apiospermum, Scedosporium prolificans; Genus Scopulariopsis such as Scopulariopsis brevicaulis; Genus Sporothrix such as Sporothrix schenckii; Genus; Trichosporon genus such as Trichosporon asahii, Trichosporon beigelii; Ustilago genus, etc.
Among these, 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.

　本発明の医療用・動物用抗真菌剤の適用が可能な感染症として、真菌症の例を以下に示す。なお、具体例はこれらのみに限定されるものではない。 An example of 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.

　本発明の医療用・動物用抗真菌剤は、全身性真菌感染症、表在性真菌感染症などのいずれにも適用できる。真菌感染症の具体例としては、肺アスペルギルス症、全身性アスペルギルス症（骨髄受容者又はAIDS患者などの免疫抑制患者において発症しやすい）などのアスペルギルス（Aspergillus）症、全身性カンジダ症などのカンジダ（Candida）症、クリプトコッカス（Cryptococcus）髄膜炎、鼻脳型ムコール症（rhinocerebral mucomycosis）、肺ムコール症、ブラストミセス症、ヒストプラスマ症、コクシジオイデス症（coccidiomycosis）、パラコクシジオイデス症（paracoccidiomycosis）、ロボ真菌症、角膜真菌症、スポロトリクム症、クロモブラストミコーシス、クロモミコーシス、フェオフィホ真菌症、接合菌症、クリプトコッカス症、播種性スポロトリクム症、白癬（ring worm）、頭部白癬（しらくも）、体部白癬（たむし）、股部白癬（いんきん）、足白癬（水虫）、爪白癬（爪水虫）、皮膚、口、又は膣のカンジダ症、マラセチア症、慢性粘膜皮膚カンジダ症、ニューモシスチス肺炎、マルネフェイ型ペニシリウム症等が挙げられる。
　また、本発明の抗真菌剤は、真菌によって引き起こされるアレルギー疾患、例えば、アレルギー性気管支肺喘息（allergic bronchopulmonary asthma）（ABPA）；喘息、鼻副鼻腔炎、又は副鼻腔炎等にも適用可能である。 The medical / animal antifungal agent of the present invention can be applied to any of systemic fungal infections, superficial fungal infections and the like. Specific examples of 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 allergic bronchopulmonary asthma (ABPA); asthma, nasal sinusitis, sinusitis and the like. is there.

　本発明の医療用・動物用抗真菌剤は、薬学的に許容される添加剤を含むことができる。添加剤は、公知の医療用薬剤において、使用されているものであれば特に制限されない。これらは、当然ながら、無菌であり、発熱性がない。また、添加剤は、抗真菌剤の剤型や投与方法などに応じて、適宜、選択することができる。 The medical / 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. In addition, the additive can be appropriately selected depending on the dosage form of the antifungal agent, the administration method, and the like.

　本発明の医療用・動物用抗真菌剤が採り得る剤型は、特に限定されず、例えば、錠剤、粉剤、粒剤、顆粒剤、カプセル剤、トローチ（飴）、ペレットなどの固体剤；シロップ、乳濁剤、懸濁剤、溶液、滴下（Pour-on)剤、点下(Spot-on)剤、などの液体剤；軟膏剤、ゲルなどの半固体調製物など；エアロゾル、蒸気などの気体剤；ナノ粒子製剤などを挙げることができる。
　本発明の医療用抗真菌剤の投与は、公知の方法で行うことができる。投与方法としては、例えば、皮下、静脈内、筋肉内、胸骨内（intrasternally）等への注入（注射）；肛門、膣などへの挿入、皮膚表面への塗布や散布、滴下などの経皮投与；口から服用などの経口投与；吸気などによる経鼻投与などを挙げることができる。 The dosage form that the medical / 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.

　経口投与用の固体剤の場合、本発明の医療用・動物用抗真菌剤に使用できる添加剤としては、シクロデキストリン又は修飾シクロデキストリン等の溶解補助剤；ラクトース、デキストロース、サッカロース、セルロース、コーンスターチ又はジャガイモデンプン等の希釈剤；シリカ、タルク、ステアリン酸、ステアリン酸マグネシウムもしくはステアリン酸カルシウム、ポリエチレングリコール等の滑沢剤；デンプン、アラビアゴム（arabic gums）、ゼラチン、メチルセルロース、カルボキシメチルセルロース又はポリビニルピロリドン等の結合剤；デンプン、アルギン酸、アルギン酸塩又はグリコール酸デンプンナトリウム等の脱凝集剤（disaggregating agents）；発泡性混合物（effervescing mixtures）；色素；甘味剤；レシチン、ポリソルベート、ラウリル硫酸（laurylsulphates）等の湿潤剤；又は一般に医薬製剤に用いられる非毒性で薬理学的に不活性な物質等を挙げることができる。これら添加剤は、混合、造粒、打錠、糖衣、又はフィルムコーティング等の公知の方法により本発明の医療用抗真菌剤に含有させることができる。 In the case of solid preparations for oral administration, 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. 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. These 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.

　経口投与用の液体剤の場合、本発明の医療用・動物用抗真菌剤に使用できる添加剤としては、シクロデキストリン又は修飾シクロデキストリン等の溶解補助剤、サッカロースを、グリセリン、マンニトール、ソルビトール、天然ガム、寒天、アルギン酸ナトリウム、ペクチン、メチルセルロース、カルボキシメチルセルロース、又はポリビニルアルコール等を挙げることができる。 In the case of a liquid agent for oral administration, as an additive that can be used in the medical / animal antifungal agent of the present invention, 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.

　筋肉内注射用の液体剤の場合、本発明の医療用・動物用抗真菌剤に使用できる添加剤としては、滅菌水、オリーブ油、オレイン酸エチル、プロピレングリコール等のグリコール類、シクロデキストリン、修飾シクロデキストリン等の溶解補助剤等を挙げることができる。さらに必要に応じて適切な量のリドカイン塩酸塩を含ませることもできる。 In the case of liquid agents for intramuscular injection, 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.

　静脈注射用の液体剤の場合、本発明の医療用・動物用抗真菌剤に使用できる添加剤としては、滅菌水等の担体；シクロデキストリン、修飾シクロデキストリン等の溶解補助剤等を挙げることができる。これらは滅菌した等張生理食塩水溶液の形態で含ませることもできる。 In the case of a liquid agent for intravenous injection, 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.

　本発明の医療用・動物用抗真菌剤に含有する化合物（I）及び化合物（II）で表される化合物又はその塩の量は、抗真菌剤の重量に対して、好ましくは８５重量％以下、より好ましくは５０重量％以下である。
　本発明の医療用・動物用抗真菌剤の用量は、投与方法、感染した真菌の種類、患者の年齢、体重、症状等に応じて適宜選択することができる。例えば、成人に対しては、経口又は非経口（注射、点滴等）的投与の場合、１日に１又は数回、０．１～１００ｍｇ／ｋｇ-体重にて投与することができる。
　また、本発明の医療用・動物用抗真菌剤は、化合物（I）及び化合物（II）で表される化合物又はその塩以外の他の薬剤と組み合わせで使用することができる。
The amount of 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.
In addition, 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.

　次に、合成実施例を示し、本発明をより具体的に説明する。ただし、本発明は以下の合成実施例によって何ら制限されるものではない。 Next, a synthetic example will be shown, and the present invention will be described more specifically. However, the present invention is not limited by the following synthetic examples.

〔実施例１〕
エチル　１－（２－（５－フルオロ－２－メトキシフェニル）－２－ヒドロキシエチル）－３－（２－イソブチルアミドエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート〔ethyl 1-(2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl)-3-(2-isobutyramidoethyl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate〕の合成
（工程１）
ジエチル　５－（３－アリルウレイド）－３－メチルチオフェン－２，４－ジカルボキシレート〔diethyl 5-(3-allylureido)-3-methylthiophene-2,4-dicarboxylate〕の合成 [Example 1]
Ethyl 1- (2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -3- (2-isobutyramide ethyl) -5-methyl-2,4-dioxo-1,2,3,4 -Tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate [ethyl 1-(2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -3- (2-isobutyramidoethyl) -5-methyl- Synthesis of 2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate] (Step 1)
Synthesis of diethyl 5- (3-allylureido) -3-methylthiophene-2,4-dicarboxylate [diethyl 5- (3-allylureido) -3-methylthiophene-2,4-dicarboxylate]

Figure JPOXMLDOC01-appb-C000027
Figure JPOXMLDOC01-appb-C000027

　ジエチル　５－アミノ－３－メチルチオフェン－２，４－ジカルボキシレート（１０ｇ）を塩化メチレン（２００ｍＬ）に溶解させ、氷冷下、トリホスゲン（４．６２ｇ）を加え、続けてトリエチルアミン（２０．８ｍＬ）を滴下したのち１．５時間室温で撹拌した。
　氷冷下、反応溶液にアリルアミン（３．６ｍＬ）を加え、室温にて一晩撹拌した。
　氷冷下、反応溶液に飽和塩化アンモニウム水溶液を加え、クロロホルムで抽出、水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥した。溶媒を減圧留去し、得られた残渣をジエチルエーテルで洗浄し目的化合物（１１．３４ｇ）を得た。収率８６％
　得られた目的物のＮＭＲデータは以下のとおり。
1H-NMR (CDCl3) δ: 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).
（工程２）
　エチル　３－アリル－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート〔ethyl 3-allyl-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate〕の合成 Dissolve diethyl 5-amino-3-methylthiophene-2,4-dicarboxylate (10 g) in methylene chloride (200 mL), add triphosgene (4.62 g) under ice cooling, followed by triethylamine (20.8 mL). ) Was added dropwise, and the mixture was stirred at room temperature for 1.5 hours.
Allylamine (3.6 mL) was added to the reaction solution under ice-cooling, and the mixture was stirred overnight at room temperature.
Under ice-cooling, a saturated aqueous solution of ammonium chloride was added to the reaction solution, extracted with chloroform, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. 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 ) δ: 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]

Figure JPOXMLDOC01-appb-C000028
Figure JPOXMLDOC01-appb-C000028

　ジエチル　５－（３－アリルウレイド）－３－メチルチオフェン－２，４－ジカルボキシレート（１１．３４ｇ）を１，４－ジオキサン（４１６ｍＬ）に溶解させ、氷冷下、ｔｅｒｔ－ブトキシカリウム（１１．２ｇ）を加え、１時間氷冷下撹拌した。
　氷冷下、反応溶液に酢酸（５．７ｍＬ）を加え、酢酸エチルで抽出、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し目的化合物（７．９６ｇ）を得た。収率８１％ 
　得られた目的物のＮＭＲデータは以下のとおり。
1H-NMR (CDCl3) δ: 5.92 (1H, dd), 5.31 (1H, dd), 5.23 (1H, d), 4.60 (2H, d), 4.35 (2H, q), 2.87 (3H, s), 1.37 (2H, t).
（工程３）
　エチル　３－アリル－１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート〔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〕の合成 Diethyl 5- (3-allyl ureide) -3-methylthiophene-2,4-dicarboxylate (11.34 g) was dissolved in 1,4-dioxane (416 mL) and tert-butoxypotassium (11) under ice-cooling. .2 g) was added, and the mixture was stirred under ice-cooling for 1 hour.
Under ice-cooling, acetic acid (5.7 mL) 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 to obtain the target compound (7.96 g). Yield 81%
The obtained NMR data of the target product is as follows.
1 1 H-NMR (CDCl 3 ) δ: 5.92 (1H, dd), 5.31 (1H, dd), 5.23 (1H, d), 4.60 (2H, d), 4.35 (2H, q), 2.87 (3H, s) ), 1.37 (2H, t).
(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

Figure JPOXMLDOC01-appb-C000029
Figure JPOXMLDOC01-appb-C000029

　エチル　３－アリル－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート（７．９６ｇ）をＮ，Ｎ－ジメチルホルムアミド（２７０ｍＬ）に溶解させ、氷冷下、２－ブロモ－１－（５－フルオロ－２－メトキシフェニル）エタン－１－オン（８．０ｇ）と炭酸カリウム（７．４５ｇ）を加え、２時間室温で撹拌した。
　氷冷下、反応溶液に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：ｎ－ヘキサン／酢酸エチル）で精製し、目的化合物（９．４２ｇ）を得た。収率７６％
　得られた目的物のＮＭＲデータは以下のとおり。
1H-NMR (CDCl3) δ: 7.65 (1H, dd), 7.30 (1H, m), 7.03 (1H, dd), 5.97-5.87 (1H, m), 5.36-5.30 (1H, m), 5.32 (2H, s), 5.21 (1H, dd), 4.63 (2H, d), 4.31 (2H, q), 4.02 (3H, s), 2.89 (3H, s), 1.34 (3H, t).
（工程４）
　エチル　１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート〔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〕の合成 Ethyl 3-allyl-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate (7.96 g) in N, N-dimethylformamide Dissolve in (270 mL), add 2-bromo-1- (5-fluoro-2-methoxyphenyl) ethane-1-one (8.0 g) and potassium carbonate (7.45 g) under ice-cooling for 2 hours. Stirred at room temperature.
Under ice-cooling, 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 (9.42 g). Yield 76%
The obtained NMR data of the target product is as follows.
1 1 H-NMR (CDCl 3 ) δ: 7.65 (1H, dd), 7.30 (1H, m), 7.03 (1H, dd), 5.97-5.87 (1H, m), 5.36-5.30 (1H, m), 5.32 (2H, s), 5.21 (1H, dd), 4.63 (2H, d), 4.31 (2H, q), 4.02 (3H, s), 2.89 (3H, s), 1.34 (3H, t).
(Step 4)
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 [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] synthesis

Figure JPOXMLDOC01-appb-C000030
Figure JPOXMLDOC01-appb-C000030

　エチル　３－アリル－１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート（７．７５ｇ）を１，４－ジオキサン（２４ｍＬ）に溶解させ、Ｎ，Ｎ－ジイソプロピルエチルアミン（１１．６ｍＬ）と蟻酸（２．５５ ｍＬ）を加えた。アルゴン雰囲気下、テトラキストリフェニルホスフィンパラジウム（０） （１．９４g）を加え、９０ ℃で二日間攪拌した。
　反応液を減圧濃縮し、得られた残渣をクロロホルムで洗浄し、目的化合物（５．６８ ｇ）を得た。収率８０％
　得られた目的物のＮＭＲデータは以下のとおり。
1H-NMR (DMSO-D6) δ: 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).
（工程５）
　エチル　３－（２－（（ｔｅｒｔ－ブトキシカルボニル）アミノ）エチル）－１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート〔ethyl 3-(2-((tert-butoxycarbonyl)amino)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〕の合成 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 (7.75 g) was dissolved in 1,4-dioxane (24 mL), and N, N-diisopropylethylamine (11.6 mL) and formic acid (2.55 mL) were added. Tetrakistriphenylphosphine palladium (0) (1.94 g) was added under an argon atmosphere, and the mixture was stirred at 90 ° C. for 2 days.
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 ) δ: 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).
(Step 5)
Ethyl 3-(2-((tert-butoxycarbonyl) amino) ethyl) -1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-1 , 2,3,4-Tetrahydrothieno [2,3-d] pyrimidin-6-carboxylate [ethyl 3-(2-((tert-butoxycarbonyl) amino) 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] synthesis

Figure JPOXMLDOC01-appb-C000031
Figure JPOXMLDOC01-appb-C000031

　エチル　１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート（５３０ｍｇ）をＮ，Ｎ－ジメチルホルムアミド（１２．６ｍＬ）に溶解させ、ｔｅｒｔ－ブチル　Ｎ－（２－ブロモエチル）カルバメート（３３８ ｍｇ）と炭酸カリウム（３４７ｍｇ）を加え、８０ ℃で４時間撹拌した。
　氷冷下、反応溶液に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：ｎ－ヘキサン／酢酸エチル）で精製し、目的化合物（５５０ｍｇ）を得た。収率７７％　得られた目的物のＮＭＲデータは以下のとおり。
1H-NMR (CDCl3) δ: 7.64 (1H, dd), 7.33-7.29 (1H, m), 7.05-7.00 (1H, m), 5.32 (2H, s), 4.31 (2H, q), 4.19 (2H, t), 4.03 (3H, s), 3.45 (2H, m), 2.89 (3H, s), 1.37(9H, s), 1.34 (3H, t).
（工程６）
　エチル　３－（２－アミノエチル）－１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート〔ethyl 3-(2-aminoethyl)-1-(2-(5-fluoro-2-methoxyphenyl)-2-oxoethyl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylate〕の合成 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.
Under ice-cooling, 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 (550 mg). Yield 77% The NMR data of the obtained target product is as follows.
1 1 H-NMR (CDCl 3 ) δ: 7.64 (1H, dd), 7.33-7.29 (1H, m), 7.05-7.00 (1H, m), 5.32 (2H, s), 4.31 (2H, q), 4.19 (2H, t), 4.03 (3H, s), 3.45 (2H, m), 2.89 (3H, s), 1.37 (9H, s), 1.34 (3H, t).
(Step 6)
Ethyl 3- (2-aminoethyl) -1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-1,2,3,4-tetrahydro Thieno [2,3-d] pyrimidine-6-carboxylate [ethyl 3- (2-aminoethyl) -1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2, Synthesis of 4-dioxo-1,2,3,4-tetrahydrothieno [2,3-d] pyrimidine-6-carboxylate]

Figure JPOXMLDOC01-appb-C000032
Figure JPOXMLDOC01-appb-C000032

　エチル　３－（２－（（ｔｅｒｔ－ブトキシカルボニル）アミノ）エチル）－１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート（４３０ ｍｇ）を、塩化メチレン（１３ ｍＬ）とトリフルオロ酢酸（１．３ ｍＬ）の混合液に溶解させ、室温で３時間撹拌した。
　溶媒を減圧留去し、目的化合物（３５０ ｍｇ）を得た。収率９９％
　得られた目的物のＮＭＲデータは以下のとおり。
1H-NMR (CDCl3) δ: 7.60 (1H, dd), 7.30-7.17 (1H, m), 7.01 (1H, dd), 5.28 (2H, s), 4.32 (2H, br s), 4.29 (2H, q), 3.99 (3H, s), 3.33 (2H, br s), 2.79 (3H, s), 1.32 (3H, t).
（工程７）
　エチル　１－（２－（５－フルオロ－２－メトキシフェニル）－２－ヒドロキシエチル）－３－（２－イソブチルアミドエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレートの合成 Ethyl 3-(2-((tert-butoxycarbonyl) amino) ethyl) -1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-1 , 2,3,4-Tetrahydrothieno [2,3-d] pyrimidin-6-carboxylate (430 mg) was dissolved in a mixture of methylene chloride (13 mL) and trifluoroacetic acid (1.3 mL). , Stirred at room temperature for 3 hours.
The solvent was distilled off under reduced pressure to obtain the target compound (350 mg). Yield 99%
The obtained NMR data of the target product is as follows.
1 1 H-NMR (CDCl 3 ) δ: 7.60 (1H, dd), 7.30-7.17 (1H, m), 7.01 (1H, dd), 5.28 (2H, s), 4.32 (2H, br s), 4.29 ( 2H, q), 3.99 (3H, s), 3.33 (2H, br s), 2.79 (3H, s), 1.32 (3H, t).
(Step 7)
Ethyl 1- (2- (5-fluoro-2-methoxyphenyl) -2-hydroxyethyl) -3- (2-isobutyramide ethyl) -5-methyl-2,4-dioxo-1,2,3,4 -Synthesis of tetrahydrothieno [2,3-d] pyrimidin-6-carboxylate

Figure JPOXMLDOC01-appb-C000033
Figure JPOXMLDOC01-appb-C000033

　エチル　３－（２－アミノエチル）－１－（２－（５－フルオロ－２－メトキシフェニル）－２－オキソエチル）－５－メチル－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－カルボキシレート（１７０ ｍｇ）を塩化メチレン（ ３．７ ｍＬ）に溶解させ、氷冷下トリエチルアミン（１０３ μＬ）とイソブチリルクロライド（５８μＬ）を加え、室温で２時間攪拌した。
　反応溶液に飽和塩化アンモニウム水溶液を加え、クロロホルムで抽出、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し、得られた残渣をテトラヒドロフラン（１．７ｍＬ）とメタノール（１．７ｍＬ）の混合液に溶解させた。氷冷下、水素化ホウ素ナトリウム（２２ｍｇ）を加え、室温で３０分撹拌した。
　反応溶液に飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出、飽和食塩水で洗浄した後、無水硫酸ナトリウムで乾燥した。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：ｎ－ヘキサン／酢酸エチル）で精製し、目的化合物（８０ ｍｇ）を得た。収率４１％
　得られた目的物のＮＭＲデータは以下のとおり。
1H-NMR (CDCl3) δ: 7.43 (1H, dd), 6.97 (1H, m), 6.83 (1H, dd), 5.88 (1H, br s), 5.64-5.59 (1H, m), 5.14 (1H, d), 4.38-4.34 (2H, m), 4.38-4.34 (2H, m), 3.96-3.90(2H, m), 3.93 (3H, s), 3.50-3.43 (1H, m), 2.83 (3H, s), 2.20 (1H, m), 1.42 (3H,q), 0.91 (6H, dd). Ethyl 3- (2-aminoethyl) -1- (2- (5-fluoro-2-methoxyphenyl) -2-oxoethyl) -5-methyl-2,4-dioxo-1,2,3,4-tetrahydro Thieno [2,3-d] pyrimidin-6-carboxylate (170 mg) was dissolved in methylene chloride (3.7 mL), and triethylamine (103 μL) and isobutyryl chloride (58 μL) were added under ice-cooling. The mixture was stirred at room temperature for 2 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.
1 1 H-NMR (CDCl 3 ) δ: 7.43 (1H, dd), 6.97 (1H, m), 6.83 (1H, dd), 5.88 (1H, br s), 5.64-5.59 (1H, m), 5.14 ( 1H, d), 4.38-4.34 (2H, m), 4.38-4.34 (2H, m), 3.96-3.90 (2H, m), 3.93 (3H, s), 3.50-3.43 (1H, m), 2.83 ( 3H, s), 2.20 (1H, m), 1.42 (3H, q), 0.91 (6H, dd).

　前記の実施例と同様の方法で製造した本発明化合物の一部を表２～表４に示す。表中には、各化合物の物性として、性状、又は融点（m.p.）を併せて示す。
　表２～表４中の、最初の段に記載されたＸ１、Ｘ７等の記号は、下記式における置換基を示す。表２及び表３中の「＝Ｏ」との記載は、Ｘ７とＸ８が一緒になって、オキソ基を形成していることを示す。表２～表４中、Ｍｅはメチル基を、Ｅｔはエチル基を、矢印は結合部位を示す。
　また、Ａ－１とＡ－２、Ａ－３とＡ－４、Ａ－５とＡ－６、Ａ－２９とＡ－３０、Ａ－３１とＡ－３２、Ａ－３３とＡ－３４、Ａ－３８とＡ－３９、Ａ－４０とＡ－４１、Ａ－４２とＡ－４４、Ａ－４３とＡ－４５、Ａ－４６とＡ－４７、Ａ－４８とＡ－４９、Ａ－５０とＡ－５１、Ａ－５３とＡ－５４、Ａ－５６とＡ－５７、Ａ－５８とＡ－５９及びＡ－６２とＡ－６３は、それぞれ立体異性の関係にある。
Ａ－４２とＡ－４４中のＸ１’における「ＣＨ＝ＮＯＥｔ」は、Ｚ体のオキシムである。
Ａ－４３とＡ－４５中のＸ１’における「ＣＨ＝ＮＯＥｔ」は、Ｅ体のオキシムである。 Tables 2 to 4 show some of the compounds of the present invention produced by the same method as in the above Examples. In the table, the physical characteristics or melting point (mp) of each compound are also shown.
Symbols such as X 1 and X 7 shown in the first column in Tables 2 to 4 indicate substituents in the following formulas. The description of "= O" in Tables 2 and 3 indicates that X 7 and X 8 are combined to form an oxo group. In Tables 2 to 4, Me indicates a methyl group, Et indicates an ethyl group, and an arrow indicates a binding site.
In addition, 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.
"CH = NOET" in X 1 'in A-42 and A-44 is the oxime of the Z-form.
"CH = NOET" in X 1 'in A-43 and A-45 is the oxime of the E-isomer.

Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-I000036
Figure JPOXMLDOC01-appb-I000037
Figure JPOXMLDOC01-appb-I000038
Figure JPOXMLDOC01-appb-C000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-I000036
Figure JPOXMLDOC01-appb-I000037
Figure JPOXMLDOC01-appb-I000038

Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-I000041
Figure JPOXMLDOC01-appb-I000042
Figure JPOXMLDOC01-appb-I000043
Figure JPOXMLDOC01-appb-I000044
Figure JPOXMLDOC01-appb-I000045
Figure JPOXMLDOC01-appb-C000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-I000041
Figure JPOXMLDOC01-appb-I000042
Figure JPOXMLDOC01-appb-I000043
Figure JPOXMLDOC01-appb-I000044
Figure JPOXMLDOC01-appb-I000045

Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-C000046
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000047

　表２～表４に示した化合物のうち、粘性オイル又はアモルファスの物性化合物については、１Ｈ－ＮＭＲデータを以下に示す。
化合物番号Ａ－１：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：0.87-1.24(m,9H), 2.45(s,3H), 3.79-4.78(m,9H), 5.39-5.44(m,1H), 6.48(s,1H), 6.76-6.99(m,2H), 7.44-7.49(m,1H), 7.64(s,1H), 7.73(s,1H)．
化合物番号Ａ－２：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：0.87-1.26(m,9H), 2.42(s,3H), 3.75-4.77(m,9H), 5.61-5.67(m,1H), 6.45(s,1H), 6.78-6.99(m,2H), 7.31-7.35(m,1H), 7.59(s,1H), 7.71(s,1H)．
化合物番号Ａ－１０：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：1.02-1.26(m,9H), 2.22-2.29(m,1H), 2.46(s,3H), 3.97-4.45(m,8H), 5.00-5.53(m,2H), 6.43(s,1H), 6.97-7.30(m,2H), 7.59-7.66(m,3H)．
化合物番号Ａ－１２：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：1.05-1.47(m,15H), 2.18-2.26(m,1H), 2.86(s,3H), 4.03(s,3H), 4.13(brs,2H), 5.30(s,2H), 6.99-7.65(m,3H)．
化合物番号Ａ－１４：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：1.05-1.47(m,15H), 2.18-2.26(m,1H), 2.45-2.50(m,2H), 2.86(s,3H), 3.72-4.41(m,11H), 5.26-5.31(m,1H), 6.79-7.04(m,2H), 7.33-7.38(m,1H)．
化合物番号Ａ－１６：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：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)．
化合物番号Ａ－２２：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：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)．
化合物番号Ａ－３７：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：0.72-1.20(m,12H), 2.11-2.18(m,1H), 2.57-2.59(m,3H), 3.32-3.40(m,1H), 3.76-3.89(m,5H), 4.10-4.65(m,5H), 4.79-4.89(m,2H), 5.35-5.44(m,1H), 5.59-5.65(m,1H), 5.95-6.03(m,1H), 6.70-6.78(m,1H), 6.83-6.92(m,1H), 7.26-7.43(m,1H)．
化合物番号Ａ－４３：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：0.75-0.94(m,6H), 1.21-1.34(m,6H), 2.09-2.18(m,1H), 2.49(s,3H), 3.78-3.90(m,2H), 3.95(s,3H), 4.10-4.34(m,3H), 4.54-4.72(m,2H), 5.21-5.74(m,2H), 6.79-6.83(m,1H), 6.91-6.98(m,1H), 7.48-7.52(m,1H), 8.27(s,1H)．
化合物番号Ａ－４４：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：0.73-0.94(m,6H), 1.24-1.41(m,6H), 2.09-2.18(m,1H), 2.62(s,3H), 3.51-3.87(m,2H), 3.89(s,3H), 4.27-4.35(m,3H), 4.61-4.77(m,2H), 5.32-5.74(m,3H), 6.79-6.83(m,1H), 6.92-6.98(m,1H), 7.40-7.43(m,1H), 7.67(s,1H)．
化合物番号Ａ－５０：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：1.02-1.06(m,6H), 1.38(t,3H), 1.72-2.62(m,9H), 2.84(s,3H), 3.45-4.36(m,11H), 4.83-5.58(m,2H), 6.79-6.82(m,1H), 6.95-7.02(m,1H), 7.24-7.27(m,1H)．
化合物番号Ａ－５７：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：0.8(t,3H), 1.25-1.45(m,4H), 1.98-2.10(m,2H), 2.42(s,3H), 2.61-2.67(m,2H), 3.75-3.93(m,5H), 4.32-5.72(m,8H), 6.48(s,1H), 6.82-7.75(m,5H)．
化合物番号Ａ－５８：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：1.25-1.45(m,5H), 1.98-2.10(m,2H), 2.42(s,3H), 2.61-2.67(m,2H), 3.75-3.93(m,5H), 4.32-5.72(m,8H), 6.48(s,1H), 6.82-7.75(m,5H)．
化合物番号Ａ－５９：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：1.25-1.45(m,5H), 1.98-2.10(m,2H), 2.42(s,3H), 2.61-2.67(m,2H), 3.75-3.93(m,5H), 4.32-5.72(m,8H), 6.48(s,1H), 6.82-7.75(m,5H)．
化合物番号Ａ－６０：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：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)．
化合物番号Ａ－６２：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：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)．
化合物番号Ａ－６３：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：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)．
化合物番号Ａ－６５：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：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)．
化合物番号Ａ－６６：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：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)．
化合物番号Ａ－６７：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：0.89(t,3H), 1.24-1.46(m,2H), 1.89-2.14(m,2H), 2.41-2.44(m,3H),  3.86-4.75(m,5H), 5.42-5.69(m,1H), 6.45-7.73(m,6H)．
化合物番号Ａ－７８：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：1.15-1.42(m,15H), 2.87(s,3H), 3.68-4.38(m,10H), 5.95(s,1H), 6.87-7.22(m,3H)．
化合物番号Ａ－８０：１Ｈ－ＮＭＲ（ＣＤＣｌ３，δｐｐｍ）：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)． Among the compounds shown in Tables 2 to 4, 1 H-NMR data are shown below for viscous oil or amorphous physical properties compounds.
Compound No. A-1: 1 1 H-NMR (CDCl 3 , δppm): 0.87-1.24 (m, 9H), 2.45 (s, 3H), 3.79-4.78 (m, 9H), 5.39-5.44 (m, 1H) , 6.48 (s, 1H), 6.76-6.99 (m, 2H), 7.44-7.49 (m, 1H), 7.64 (s, 1H), 7.73 (s, 1H).
Compound No. A-2: 1 1 H-NMR (CDCl 3 , δppm): 0.87-1.26 (m, 9H), 2.42 (s, 3H), 3.75-4.77 (m, 9H), 5.61-5.67 (m, 1H) , 6.45 (s, 1H), 6.78-6.99 (m, 2H), 7.31-7.35 (m, 1H), 7.59 (s, 1H), 7.71 (s, 1H).
Compound No. A-10: 1 1 H-NMR (CDCl 3 , δppm): 1.02-1.26 (m, 9H), 2.22-2.29 (m, 1H), 2.46 (s, 3H), 3.97-4.45 (m, 8H) , 5.00-5.53 (m, 2H), 6.43 (s, 1H), 6.97-7.30 (m, 2H), 7.59-7.66 (m, 3H).
Compound No. A-12: 1 1 H-NMR (CDCl 3 , δppm): 1.05-1.47 (m, 15H), 2.18-2.26 (m, 1H), 2.86 (s, 3H), 4.03 (s, 3H), 4.13 (brs, 2H), 5.30 (s, 2H), 6.99-7.65 (m, 3H).
Compound No. A-14: 1 1 H-NMR (CDCl 3 , δppm): 1.05-1.47 (m, 15H), 2.18-2.26 (m, 1H), 2.45-2.50 (m, 2H), 2.86 (s, 3H) , 3.72-4.41 (m, 11H), 5.26-5.31 (m, 1H), 6.79-7.04 (m, 2H), 7.33-7.38 (m, 1H).
Compound No. A-16: 1 1 H-NMR (CDCl 3 , δppm): 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 , δppm): 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).
Compound No. A-37: 1 1 H-NMR (CDCl 3 , δppm): 0.72-1.20 (m, 12H), 2.11-2.18 (m, 1H), 2.57-2.59 (m, 3H), 3.32-3.40 (m, 1H), 3.76-3.89 (m, 5H), 4.10-4.65 (m, 5H), 4.79-4.89 (m, 2H), 5.35-5.44 (m, 1H), 5.59-5.65 (m, 1H), 5.95- 6.03 (m, 1H), 6.70-6.78 (m, 1H), 6.83-6.92 (m, 1H), 7.26-7.43 (m, 1H).
Compound No. A-43: 1 1 H-NMR (CDCl 3 , δppm): 0.75-0.94 (m, 6H), 1.21-1.34 (m, 6H), 2.09-2.18 (m, 1H), 2.49 (s, 3H) , 3.78-3.90 (m, 2H), 3.95 (s, 3H), 4.10-4.34 (m, 3H), 4.54-4.72 (m, 2H), 5.21-5.74 (m, 2H), 6.79-6.83 (m, 1H), 6.91-6.98 (m, 1H), 7.48-7.52 (m, 1H), 8.27 (s, 1H).
Compound No. A-44: 1 1 H-NMR (CDCl 3 , δppm): 0.73-0.94 (m, 6H), 1.24-1.41 (m, 6H), 2.09-2.18 (m, 1H), 2.62 (s, 3H) , 3.51-3.87 (m, 2H), 3.89 (s, 3H), 4.27-4.35 (m, 3H), 4.61-4.77 (m, 2H), 5.32-5.74 (m, 3H), 6.79-6.83 (m, 1H), 6.92-6.98 (m, 1H), 7.40-7.43 (m, 1H), 7.67 (s, 1H).
Compound No. A-50: 1 1 H-NMR (CDCl 3 , δppm): 1.02-1.06 (m, 6H), 1.38 (t, 3H), 1.72-2.62 (m, 9H), 2.84 (s, 3H), 3.45 -4.36 (m, 11H), 4.83-5.58 (m, 2H), 6.79-6.82 (m, 1H), 6.95-7.02 (m, 1H), 7.24-7.27 (m, 1H).
Compound No. A-57: 1 1 H-NMR (CDCl 3 , δppm): 0.8 (t, 3H), 1.25-1.45 (m, 4H), 1.98-2.10 (m, 2H), 2.42 (s, 3H), 2.61 -2.67 (m, 2H), 3.75-3.93 (m, 5H), 4.32-5.72 (m, 8H), 6.48 (s, 1H), 6.82-7.75 (m, 5H).
Compound No. A-58: 1 1 H-NMR (CDCl 3 , δppm): 1.25-1.45 (m, 5H), 1.98-2.10 (m, 2H), 2.42 (s, 3H), 2.61-2.67 (m, 2H) , 3.75-3.93 (m, 5H), 4.32-5.72 (m, 8H), 6.48 (s, 1H), 6.82-7.75 (m, 5H).
Compound No. A-59: 1 1 H-NMR (CDCl 3 , δppm): 1.25-1.45 (m, 5H), 1.98-2.10 (m, 2H), 2.42 (s, 3H), 2.61-2.67 (m, 2H) , 3.75-3.93 (m, 5H), 4.32-5.72 (m, 8H), 6.48 (s, 1H), 6.82-7.75 (m, 5H).
Compound No. A-60: 1 1 H-NMR (CDCl 3 , δppm): 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. A-62: 1 1 H-NMR (CDCl 3 , δppm): 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 , δppm): 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).
Compound No. A-65: 1 1 H-NMR (CDCl 3 , δppm): 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 , δppm): 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).
Compound No. A-67: 1 1 H-NMR (CDCl 3 , δppm): 0.89 (t, 3H), 1.24-1.46 (m, 2H), 1.89-2.14 (m, 2H), 2.41-2.44 (m, 3H) , 3.86-4.75 (m, 5H), 5.42-5.69 (m, 1H), 6.45-7.73 (m, 6H).
Compound No. A-78: 1 1 H-NMR (CDCl 3 , δppm): 1.15-1.42 (m, 15H), 2.87 (s, 3H), 3.68-4.38 (m, 10H), 5.95 (s, 1H), 6.87 -7.22 (m, 3H).
Compound No. A-80: 1 1 H-NMR (CDCl 3 , δppm): 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).

〔生物試験〕
　本発明のチエノピリミジン化合物が、農園芸用殺菌剤の有効成分として有用であることを以下の試験例で示す。 [Biological test]
The following test examples show that the thienopyrimidine compound of the present invention is useful as an active ingredient of a fungicide for agriculture and horticulture.

（試験用乳剤の調製）
　本発明のチエノピリミジン化合物５重量部、N、N－ジメチルホルムアミド９３．５重量部、及びポリオキシエチレンソルビタンモノラウレート（ＴＷＥＥＮ（登録商標）２０）１．５重量部を混合し、溶解させて、有効成分５％の乳剤（Ｉ）を得た。 (Preparation of test emulsion)
5 parts by weight of the thienopyrimidine compound of the present invention, 93.5 parts by weight of N, N-dimethylformamide, and 1.5 parts by weight of polyoxyethylene sorbitan monolaurate (TWEEN® 20) are mixed and dissolved. , An emulsion (I) of 5% active ingredient was obtained.

　防除価は、下記の式により計算した。 The control price was calculated by the following formula.

［数１］
防除価（％）＝１００－{処理区における病斑面積率／無処理区における病斑面積率}×１００ [Number 1]
Control value (%) = 100- {Ratio of lesion area in treated plot / Ratio of lesion area in untreated plot} × 100

　（試験例１）リンゴ黒星病防除試験
　乳剤（Ｉ）にチエノピリミジン化合物濃度が１２５ｐｐｍになるように水を加え、溶解させて薬剤溶液を得た。続いて育苗用ポットで栽培したリンゴ幼苗（品種「王林」、３～４葉期）に、前記薬剤溶液を散布した。風乾後、リンゴ黒星病菌（Venturia inaequalis）の分生胞子を接種した（処理区）。対照として、薬剤溶液を散布しなかったリンゴ幼苗に同様に接種した（無処理区）。それらを、明暗を１２時間毎に繰り返す２０℃の湿室に静置した。
　接種から２週間経過した日にリンゴ幼苗の葉を目視観察して、病斑面積率を求め、防除価を算出した。 (Test Example 1) Apple scab control test Water was added to the emulsion (I) so that the concentration of the thienopyrimidine compound was 125 ppm, and the mixture was dissolved to obtain a drug solution. Subsequently, the chemical solution was sprayed on apple seedlings (cultivar "Orin", 3-4 leaf stage) cultivated in a seedling raising pot. After air drying, conidia of apple scab (Venturia inaequalis) were inoculated (treatment plot). As a control, apple seedlings that were not sprayed with the drug solution were similarly inoculated (untreated plot). They were allowed to stand in a wet room at 20 ° C., which repeats light and dark every 12 hours.
On the day 2 weeks after inoculation, the leaves of apple seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

　表５に記載のチエノピリミジン化合物について、リンゴ黒星病防除試験を行った。いずれの化合物も７５％以上の防除価を示した。 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.

Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000048

（試験例２）キュウリ灰色かび病防除試験
　乳剤（Ｉ）にチエノピリミジン化合物濃度が１２５ｐｐｍになるように水を加え、溶解させて薬剤溶液を得た。続いて育苗用ポットで栽培したキュウリ幼苗（品種「地這」系、子葉期）に、前記薬剤溶液を散布した。風乾後、キュウリ灰色かび病菌（Botrytis cinerea）の分生胞子懸濁液を滴下接種した（処理区）。対照として、薬剤溶液を散布しなかったキュウリ幼苗に上記と同じ方法で滴下接種した（無処理区）。それらを２０℃の湿室に静置した。
　接種から４日間経過した日にキュウリ幼苗の葉を目視観察して、病斑面積率を求め、防除価を算出した。 (Test Example 2) Cucumber Botrytis cinerea 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 drug solution was sprayed on cucumber seedlings (cultivar "Crawling" type, cotyledon stage) cultivated in a seedling raising pot. After air-drying, a suspension of conidia of Botrytis cinerea was inoculated dropwise (treatment group). As a control, cucumber seedlings not sprayed with the drug solution were inoculated by dropping in the same manner as above (untreated plot). They were allowed to stand in a wet room at 20 ° C.
On the day 4 days after inoculation, the leaves of the cucumber seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

　表６に記載のチエノピリミジン化合物について、キュウリ灰色かび病防除試験を行った。いずれの化合物も７５％以上の防除価を示した。 A 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.

Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000049

（試験例３）コムギうどんこ病防除試験
　乳剤（Ｉ）にチエノピリミジン化合物濃度が１２５ｐｐｍになるように水を加え、溶解させて薬剤溶液を得た。続いて育苗用ポットで栽培したコムギ幼苗（品種「チホク」、１～２葉期）に前記薬剤溶液を散布した。風乾後、コムギうどんこ病菌（Erysiphe graminis f.sp.tritici）の分生胞子を振りかけて接種した（処理区）。対照として、薬剤溶液を散布しなかったコムギ幼苗に上記と同じ方法で接種した（無処理区）。それらを２０℃の温室に静置した。
　接種から６日間経過した日にコムギ幼苗の葉を目視観察して、病斑面積率を求め、防除価を算出した。 (Test Example 3) Wheat powdery mildew 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 "Chihoku", 1-2 leaf stage) cultivated in a seedling raising pot. After air-drying, conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were sprinkled and inoculated (treatment plot). As a control, 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 6 days after inoculation, the leaves of wheat seedlings were visually observed to determine the lesion area ratio, and the control value was calculated.

　表７に記載のチエノピリミジン化合物について、コムギうどんこ病防除試験を行った。いずれの化合物も７５％以上の防除価を示した。 A wheat powdery mildew control test was conducted on the thienopyrimidine compounds listed in Table 7. Both compounds showed a control value of 75% or more.

Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000050

（試験例４）コムギ赤さび病防除試験
　乳剤（Ｉ）にチエノピリミジン化合物濃度が１２５ｐｐｍになるように水を加え、溶解させて薬剤溶液を得た。続いて育苗用ポットで栽培したコムギ幼苗（品種「農林６１号」、１～２葉期）に前記薬剤溶液を散布した。風乾後、薬剤溶液を散布したコムギ幼苗にコムギ赤さび病菌（Puccinia recondita）の夏胞子をふり掛けて接種した（処理区）。対照として、薬剤溶液を散布しなかったコムギ幼苗に上記と同様にして接種した（無処理区）。それらを２０℃の温室に静置した。
　接種から１２日間経過した日にコムギ苗の葉を目視観察して、病斑面積率を求め、防除価を算出した。 (Test Example 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). As a control, 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.

　表８に記載のチエノピリミジン化合物について、コムギ赤さび病防除試験を行った。いずれの化合物も７５％以上の防除価を示した。 A wheat red rust control test was conducted on the thienopyrimidine compounds shown in Table 8. Both compounds showed a control value of 75% or more.

Figure JPOXMLDOC01-appb-T000051
（試験例５）コムギうどんこ病種子処理試験
　コムギ種子（品種「チホク」）に対して、（チエノピリミジン化合物の重量）／（種子の重量）が１００ｇ／１００ｋｇとなるように乳剤（Ｉ）を種子処理した。これら種子をポットに播種し、８～１０日後にコムギうどんこ病菌（Ｅｒｙｓｉｐｈｅ　ｇｒａｍｉｎｉｓ　ｆ．ｓｐ．ｔｒｉｔｉｃｉ）の分生胞子を振りかけて接種した（処理区）。対照として、薬剤を処理しなかったコムギ幼苗に上記と同じ方法で接種した（無処理区）。それらを２０℃の温室に静置した。
　接種から７日間経過した日にコムギ幼苗の葉を目視観察して、病斑面積率を求め、防除価を算出した。
Figure JPOXMLDOC01-appb-T000051
 (Test Example 5) 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.

　表９に記載のチエノピリミジン化合物について、コムギうどんこ病種子処理試験を行った。いずれの化合物も７５％以上の防除価を示した。 A wheat powdery mildew seed treatment test was conducted on the thienopyrimidine compounds shown in Table 9. Both compounds showed a control value of 75% or more.

Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000052

（試験例６）コムギうどんこ病土壌潅注処理試験
　コムギ種子（品種「チホク」）を播種したポット（５．５ｃｍ×５．５ｃｍ）に、乳剤（Ｉ）に水を加えてチエノピリミジン化合物の濃度を１００ｐｐｍにした薬剤溶液を１０ｍＬ潅注し、８～１０日後にコムギうどんこ病菌（Ｅｒｙｓｉｐｈｅ　ｇｒａｍｉｎｉｓ　ｆ．ｓｐ．ｔｒｉｔｉｃｉ）の分生胞子を振りかけて接種した（処理区）。対照として、薬剤を処理しなかったコムギ幼苗に上記と同じ方法で接種した（無処理区）。それらを２０℃の温室に静置した。
　接種から７日間経過した日にコムギ幼苗の葉を目視観察して、病斑面積率を求め、防除価を算出した。 (Test Example 6) 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.

　表１０に記載のチエノピリミジン化合物について、コムギうどんこ病土壌潅注処理試験を行った。いずれの化合物も７５％以上の防除価を示した。 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.

Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000053

　本発明のチエノピリミジン化合物が、医療用・動物用抗真菌剤の有効成分として有用であることを以下の試験例で示す。
（試験例７）Ｆｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍに対する抗菌試験
　乳剤（Ｉ）にチエノピリミジン化合物の濃度が１２５ｐｐｍになるように水を加え、溶解させて薬剤溶液を得た。
　ジャガイモショ糖酵母エキス培地にＦｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍの胞子を添加して分散させ、さらに上記の薬剤溶液を、チエノピリミジン化合物の培養液中の濃度が１５．６ｐｐｍとなるように添加混合し、これらを９６穴マイクロプレート上に分注し、暗所、２０℃で４日間培養した。
　培養後、マイクロプレートリーダーで波長４０５ｎｍにおける濁度を測定し、無処理の場合と比較してＦｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍの生育阻害率（％）を求めた。 The following 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. It was dispensed on a microplate and cultured in a dark place at 20 ° C. for 4 days.
After culturing, the turbidity at a wavelength of 405 nm was measured with a microplate reader, and the growth inhibition rate (%) of Fusarium graminearum was determined as compared with the case of no treatment.

　表１１に記載のチエノピリミジン化合物について、Ｆｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍに対する抗菌試験を行った。いずれの化合物も５０％以上の優れた生育阻害率を示した。 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.

Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054

（試験例８）Ａｓｐｅｒｇｉｌｌｕｓ　ｎｉｇｅｒに対する抗菌試験
　Ｖｏｇｅｌ培地にＡｓｐｅｒｇｉｌｌｕｓ　ｎｉｇｅｒの胞子を添加して分散させ、さらにジメチルスルホキシドに溶解したチエノピリミジン化合物を２５ｐｐｍとなるように添加混合し、これらを９６穴マイクロプレート上に分注し、暗所、２５℃で４日間培養した。
　培養後、マイクロプレートリーダーで波長４０５ｎｍにおける濁度を測定し、無処理の場合と比較してＡｓｐｅｒｇｉｌｌｕｓ　ｎｉｇｅｒの生育阻害率（％）を求めた。 (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. Was dispensed and cultured in a dark place at 25 ° C. for 4 days.
After culturing, the turbidity at a wavelength of 405 nm was measured with a microplate reader, and the growth inhibition rate (%) of Aspergillus niger was determined as compared with the case of no treatment.

　表１２に記載のチエノピリミジン化合物について、Ａｓｐｅｒｇｉｌｌｕｓ　ｎｉｇｅｒに対する抗菌試験を行った。いずれの化合物も５０％以上の優れた生育阻害率を示した。 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.

Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055

　本発明のチエノピリミジン化合物の中から無作為に選択したものが、上記のような効果を奏することから、本発明のチエノピリミジン化合物は、例示しきれなかった化合物を含め、殺菌効果を有し、植物体に薬害を生じることがなく、人畜魚類に対する毒性や環境への影響が少ない化合物であり、農薬及び医療用・動物用抗真菌剤として有用である。 Since randomly selected thienopyrimidine compounds of the present invention exert the above-mentioned effects, 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.

Claims (7)

　式（Ｉ）で表される化合物又はその塩。
Figure JPOXMLDOC01-appb-C000001
 〔式（Ｉ）中、
　Ｘ1は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基、又はＲ１Ｏ－Ｎ＝ＣＲ６－で表される基を示し；
　Ｒ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ２は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ３は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ４は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよく、
　Ｒ５は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒ６は、水素原子、アミノ基、又は置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｘ２は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、又はＲ３Ｒ４Ｎ－ＳＯ２－で表される基を示し；
　Ｒ１～Ｒ５は、Ｘ１におけるそれらと同様の意味を示す。
　Ｘ３ 、Ｘ４ 、Ｘ５ 及びＸ６は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基を示し；
　Ｘ３ とＸ４は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｘ４ とＸ５ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｘ５ とＸ６  は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｑは、式（Ｑ－１）又は式（Ｑ－２）で表される基である。
Figure JPOXMLDOC01-appb-C000002
 　（式（Ｑ－１）及び式（Ｑ－２）中、矢印は結合部位を示し、
　Ｒcは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、Ｃ１～６アルキルアミノ基又は置換若しくは無置換のＣ３～６シクロアルキル基であり、Ｒｄ は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ１～６アルキルカルボニル基である。）
　Ａは、置換若しくは無置換のＣ１～６アルキレン基、置換若しくは無置換のＣ２～６アルケニレン基、置換若しくは無置換のＣ２～６アルキニレン基、又は置換若しくは無置換のＣ３～６シクロアルキレン基を示し；
　Ｙは、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～１０員環のヘテロシクリル基を示す。〕 A compound represented by the formula (I) or a salt thereof.
Figure JPOXMLDOC01-appb-C000001
 [In formula (I),
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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl group ring, a substituted or unsubstituted 5-6 membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO A group represented by-, a group represented by R 3 R 4 N-, a group represented by R 3 R 4 N-CO-, a group represented by R 1 -CO-O-, a group represented by R 1- CO. -NR 5 - group represented by, R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O Group represented by-, group represented by R 3 R 4 N-CO-NR 5- , group represented by R 2 SO 2- NR 5- , represented by R 3 R 4 N-SO 2- Or a group represented by 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. 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 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.
Here, 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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO-, a group represented by, R 3 R 4 Group represented by N-, group represented by R 3 R 4 N-CO-, group represented by R 1- CO-O-, group represented by R 1- CO-NR 5- , R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O- , a group represented by, R 3 R 4 Indicates a group represented by N-CO-NR 5- , a group represented by R 2 SO 2- NR 5- , or a group represented by R 3 R 4 N-SO 2-;
R 1 to R 5 have the same meanings as those in X 1.
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).
Figure JPOXMLDOC01-appb-C000002
 (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. ] 　ＡにおけるＣ１～６アルキレン基又はＣ２～６アルケニレン基上の置換基が、
　ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、メルカプト基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の３～６員環のヘテロシクリル基、置換若しくは無置換の３～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒａ１－ＣＯ－で表される基、カルボキシ基、Ｒｂ１－Ｏ－ＣＯ－で表される基、Ｒｃ１Ｒｄ１Ｎ－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－で表される基、Ｒａ１－ＣＯ－Ｏ－で表される基、Ｒａ１－ＣＯ－ＮＲｅ１－で表される基、Ｒｂ１－Ｏ－ＣＯ－Ｏ－で表される基、Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－Ｏ－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＣＯ－ＮＲｅ１－で表される基、Ｒｂ１ＳＯ２－ＮＲｅ１－で表される基、Ｒｃ１Ｒｄ１Ｎ－ＳＯ２－で表される基、Ｒａ１Ｏ－Ｎ＝ＣＲｆ１－で表される基、Ｒｇ１Ｒｈ１Ｃ＝Ｎ－Ｏ－で表される基、オキソ基（Ｏ＝）、チオキソ基（Ｓ＝）、Ｒａ１－Ｎ＝で表される二価の基、Ｒａ１Ｏ－Ｎ＝で表される二価の基、Ｒｃ１Ｒｄ１Ｎ－Ｎ＝で表される二価の基、Ｒａ１－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基、Ｒｂ１－Ｏ－ＣＯ－ＮＲｅ１－Ｎ＝で表される二価の基、Ｒｂ１ＳＯ２－ＮＲｅ１－Ｎ＝で表される二価の基からなる群より選択される１又は２以上の置換基であって；
　Ｒａ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｂ１は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｃ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｄ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、ここで、Ｒｃ１とＲｄ１は、一緒になって二価の有機基を形成してもよく、
　Ｒｅ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒｆ１は、水素原子、又は置換若しくは無置換のＣ１～６アルキル基を示し、
　Ｒｇ１は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒｈ１は、水素原子、又は置換若しくは無置換のＣ１～６アルキル基を示し、ここで、Ｒｇ１とＲｈ１は、一緒になって二価の有機基を形成してもよく； 
　Ｃ１～６アルキレン基又はＣ２～６アルケニレン基上の置換基は２以上ある場合、そのうちの２つが一緒になって二価の有機基を形成してもよいものである；
請求項１に記載の化合物又はその塩。 Substituents on the C1-6 alkylene group or C2-6 alkenylene group in A
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. Alternatively, 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. Substituted C6-10 aryloxy group, substituted or unsubstituted C6-10 arylthio group, substituted or unsubstituted C6-10 arylsulfinyl group, substituted or unsubstituted C6-10 arylsulfonyl group, substituted or unsubstituted 3 to 6-membered heterocyclyl group ring, a substituted or unsubstituted 3-6 membered heterocyclyloxy group ring, nitro group, cyano group, a group represented by R a1 -CO-, carboxy group, R b1 -O-CO- a group represented by, R c1 R d1 N- group represented by, R c1 R d1 N-CO-, a group represented by, R a1 -CO-O-, a group represented by, R a1 -CO- Group represented by NR e1- , group represented by R b1- O-CO-O-, group represented by R b1- O-CO-NR e1- , R c1 R d1 N-CO-O- The group represented by R c1 R d1 N-CO-NR e1- , the group represented by R b1 SO 2- NR e1- , and the group represented by R c1 R d1 N-SO 2-. Group, group represented by R a1 ON = CR f1- , group represented by R g1 R h1 C = NO-, oxo group (O =), thioxo group (S =), R a1- A divalent group represented by N =, a divalent group represented by R a1 ON =, a divalent group represented by R c1 R d1 NN =, R a1- CO-NR e1 A divalent group represented by -N =, a divalent group represented by R b1- O-CO-NR e1- N =, a divalent group represented by R b1 SO 2- NR e1- N = One or more substituents selected from the group consisting of groups;
Ra1 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 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. Alternatively, 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;
The compound according to claim 1 or a salt thereof. 　式（Ｉ）が式（II）で表される、請求項１又は２に記載の化合物又はその塩。
Figure JPOXMLDOC01-appb-C000003
 ［式（II）中、
　Ｘ１’は、置換若しくは無置換のＣ１～６アルコキシカルボニル基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換の５～６員ヘテロアリール基、シアノ基又は式「－ＣＲa’ ＝Ｎ－ＯＲb ’」で表される基である。
　Ｒa’ は、水素原子又はアミノ基であり、Ｒb’ は、水素原子又は置換又は無置換のＣ１～６アルキル基である。
　Ｘ２’は、置換又は無置換のＣ１～６アルキル基である。
　Ｘ３ 、Ｘ４ 、Ｘ５ 及びＸ６は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基である。
　Ｘ３ とＸ４ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｘ４ とＸ５ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｘ５ とＸ６ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよい。
　Ｘ７ は、水酸基、置換若しくは無置換のＣ１～６アルコキシ基又は置換若しくは無置換のＣ１～６アルキルカルボニルオキシ基である。
　Ｘ８ は、水素原子である。
　Ｘ７ とＸ８ は、それらが一緒になって、オキソ基、又は置換若しくは無置換のＣ１～６アルコキシイミノ基を形成してもよい。
　Ｘ９ 及びＸ１０ は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基である。
　Ｘ８とＸ１０ は、それらが一緒になって、単結合を形成してもよい。
　Ｘ１１は、ハロゲノ基又は置換若しくは無置換のＣ１～６アルコキシ基である。
　ｎは、０～５のいずれかの整数であり、ｎが２以上のときＸ11は互いに同じでも異なってもよい。
　Ｑは、式（Ｑ－１）又は式（Ｑ－２）で表される基である。
Figure JPOXMLDOC01-appb-C000004
 　（式（Ｑ－１）及び式（Ｑ－２）中、矢印は結合部位を示し、
　Ｒcは、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、Ｃ１～６アルキルアミノ基又は置換若しくは無置換のＣ３～６シクロアルキル基である。Ｒｄ は、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ１～６アルキルカルボニル基である。）］ The compound according to claim 1 or 2, or a salt thereof, wherein formula (I) is represented by formula (II).
Figure JPOXMLDOC01-appb-C000003
 [In equation (II),
X 1 'are members independently selected from substituted or unsubstituted C1 ~ 6 alkoxycarbonyl group, a substituted or unsubstituted C1 ~ 6 alkyl group, a substituted or unsubstituted 5-6 membered heteroaryl group, a cyano group, or the formula "-CR a' = N-OR b' "is a group.
R a'is a hydrogen atom or amino group, and 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).
Figure JPOXMLDOC01-appb-C000004
 (In equations (Q-1) and (Q-2), the arrows indicate the binding sites.
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. )] 　請求項１～３のいずれかに記載の化合物及びその塩からなる群から選ばれる、少なくとも１つを有効成分として含有する農園芸用殺菌剤。 An agricultural and horticultural fungicide containing at least one as an active ingredient, selected from the group consisting of the compound according to any one of claims 1 to 3 and a salt thereof. 　種子処理用である、請求項４に記載の農園芸用殺菌剤。 The agricultural and horticultural fungicide according to claim 4, which is used for seed processing. 　請求項１～３のいずれかに記載の化合物、及びそれらの塩からなる群から選ばれる少なくとも１つを有効成分として含有する医療用・動物用抗真菌剤。 A medical / animal antifungal agent containing at least one selected from the group consisting of the compound according to any one of claims 1 to 3 and a salt thereof as an active ingredient. 　式（IV）で表される化合物又はその塩。
Figure JPOXMLDOC01-appb-C000005
 〔式（IV）中、
　Ｘ１は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールチオ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＳＯ２－で表される基、又はＲ１Ｏ－Ｎ＝ＣＲ６－で表される基を示し；
　Ｒ１は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ２は、それぞれ独立に、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ３は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～６員環のヘテロシクリル基を示し、
　Ｒ４は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　ここで、Ｒ３とＲ４は、一緒になって二価の有機基を形成してもよく、
　Ｒ５は、それぞれ独立に、水素原子、置換若しくは無置換のＣ１～６アルキル基、又は置換若しくは無置換のＣ６～１０アリール基を示し、
　Ｒ６は、水素原子、アミノ基、又は置換若しくは無置換のＣ１～６アルキル基を示す。
　Ｘ２は、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ２～６アルケニル基、置換若しくは無置換のＣ２～６アルキニル基、水酸基、置換若しくは無置換のＣ１～６アルコキシ基、置換若しくは無置換のＣ２～６アルケニルオキシ基、置換若しくは無置換のＣ２～６アルキニルオキシ基、置換若しくは無置換のＣ１～６アルキルチオ基、置換若しくは無置換のＣ１～６アルキルスルフィニル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、置換若しくは無置換のＣ３～６シクロアルキル基、置換若しくは無置換のＣ３～６シクロアルキルオキシ基、置換若しくは無置換のＣ６～１０アリール基、置換若しくは無置換のＣ６～１０アリールオキシ基、置換若しくは無置換のＣ６～１０アリールスルフィニル基、置換若しくは無置換のＣ６～１０アリールスルホニル基、置換若しくは無置換の５～６員環のヘテロシクリル基、置換若しくは無置換の５～６員環のヘテロシクリルオキシ基、ニトロ基、シアノ基、Ｒ１－ＣＯ－で表される基、カルボキシ基、Ｒ２－Ｏ－ＣＯ－で表される基、Ｒ３Ｒ４Ｎ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－で表される基、Ｒ１－ＣＯ－Ｏ－で表される基、Ｒ１－ＣＯ－ＮＲ５－で表される基、Ｒ２－Ｏ－ＣＯ－Ｏ－で表される基、Ｒ２－Ｏ－ＣＯ－ＮＲ５－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－Ｏ－で表される基、Ｒ３Ｒ４Ｎ－ＣＯ－ＮＲ５－で表される基、Ｒ２ＳＯ２－ＮＲ５－で表される基、又はＲ３Ｒ４Ｎ－ＳＯ２－で表される基を示し；
　Ｒ１～Ｒ５は、Ｘ１におけるそれらと同様の意味を示す。
　Ｘ3 、Ｘ4 、Ｘ5 及びＸ6 は、それぞれ独立して、水素原子又は置換若しくは無置換のＣ１～６アルキル基を示し；
　Ｘ３ とＸ４ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｘ４ とＸ５ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｘ５ とＸ６ は、それらが一緒になって、Ｃ２～６アルキレン基を形成してもよく；
　Ｑ’は、ＮＨ２又は ＣＨ２ＮＨ２で表される基を示す。
　Ａは、置換若しくは無置換のＣ１～６アルキレン基、置換若しくは無置換のＣ２～６アルケニレン基、置換若しくは無置換のＣ２～６アルキニレン基、又は置換若しくは無置換のＣ３～６シクロアルキレン基を示し；
　Ｙは、置換若しくは無置換のＣ６～１０アリール基、又は置換若しくは無置換の５～１０員環のヘテロシクリル基を示す。〕
  A compound represented by the formula (IV) or a salt thereof.
Figure JPOXMLDOC01-appb-C000005
 [In equation (IV),
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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylthio groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl group ring, a substituted or unsubstituted 5-6 membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO A group represented by-, a group represented by R 3 R 4 N-, a group represented by R 3 R 4 N-CO-, a group represented by R 1 -CO-O-, a group represented by R 1- CO. -NR 5 - group represented by, R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O Group represented by-, group represented by R 3 R 4 N-CO-NR 5- , group represented by R 2 SO 2- NR 5- , represented by R 3 R 4 N-SO 2- Or a group represented by 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. 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 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.
Here, 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 C6-10 aryl groups, substituted or Unsubstituted C6-10 aryloxy groups, substituted or unsubstituted C6-10 arylsulfinyl groups, substituted or unsubstituted C6-10 arylsulfonyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyl groups, substituted or unsubstituted 5- to 6-membered heterocyclyloxy group ring, nitro group, cyano group, the group represented by R 1 -CO-, carboxy group, R 2 -O-CO-, a group represented by, R 3 R 4 Group represented by N-, group represented by R 3 R 4 N-CO-, group represented by R 1- CO-O-, group represented by R 1- CO-NR 5- , R 2 -O-CO-O-, a group represented by, R 2 -O-CO-NR 5 - , a group represented by, R 3 R 4 N-CO -O- , a group represented by, R 3 R 4 Indicates a group represented by N-CO-NR 5- , a group represented by R 2 SO 2- NR 5- , or a group represented by R 3 R 4 N-SO 2-;
R 1 to R 5 have the same meanings as those in X 1.
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. ]
PCT/JP2020/045190 2019-12-05 2020-12-04 2,4-dioxo-1,4-dihydrothienopyrimidine compound, agricultural or horticultural fungicidal agent, or medical/animal antifungal agent, containing this Ceased WO2021112213A1 (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008143262A1 (en) * 2007-05-21 2008-11-27 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof
JP2014533281A (en) * 2011-11-11 2014-12-11 ニンバス アポロ， インコーポレイテッド ACC inhibitors and uses thereof
JP2016520064A (en) * 2013-05-10 2016-07-11 ニンバス アポロ，インコーポレーテッド ACC inhibitors and uses thereof
JP2018538246A (en) * 2015-10-26 2018-12-27 ギリアド アポロ， エルエルシー ACC inhibitors and uses thereof
WO2019020041A1 (en) * 2017-07-26 2019-01-31 南京圣和药业股份有限公司 Compound as acc inhibitor and use thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008143262A1 (en) * 2007-05-21 2008-11-27 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof
JP2014533281A (en) * 2011-11-11 2014-12-11 ニンバス アポロ， インコーポレイテッド ACC inhibitors and uses thereof
JP2016520064A (en) * 2013-05-10 2016-07-11 ニンバス アポロ，インコーポレーテッド ACC inhibitors and uses thereof
JP2018538246A (en) * 2015-10-26 2018-12-27 ギリアド アポロ， エルエルシー ACC inhibitors and uses thereof
WO2019020041A1 (en) * 2017-07-26 2019-01-31 南京圣和药业股份有限公司 Compound as acc inhibitor and use thereof

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