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WO2010032881A1 - Agent de contrôle phytosanitaire - Google Patents

Agent de contrôle phytosanitaire Download PDF

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Publication number
WO2010032881A1
WO2010032881A1 PCT/JP2009/066868 JP2009066868W WO2010032881A1 WO 2010032881 A1 WO2010032881 A1 WO 2010032881A1 JP 2009066868 W JP2009066868 W JP 2009066868W WO 2010032881 A1 WO2010032881 A1 WO 2010032881A1
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Prior art keywords
group
formula
alkyl
cycloalkyl
alkoxy
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Japanese (ja)
Inventor
阪口裕史
久保田真由美
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—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
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2

Definitions

  • the present invention relates to a plant disease control agent.
  • a 1 means a quinolin-6-yl group, a benzothiazol-6-yl group or a [1,5] naphthyridin-2-yl group
  • X 1 is a group represented by the formula —C ( ⁇ O) —NH—, a group represented by the formula —NH—C ( ⁇ O) —, a group represented by the formula —C ( ⁇ S) —NH—.
  • R 12 represents a substituent listed in the following substituent group a-3; [Substituent group a-3] ⁇ Hydrogen atom halogen atom C1-C8 alkyl group, A C2-C9 alkenyl group, A C2-C9 alkynyl group, A C7-C16 aralkyl group, A C7-C16 aralkyloxy group, A C7-C16 phenoxyalkyl group, A C1-C8 alkoxy group, A C3-C9 alkynyloxy group, C3-C9 alkenyloxy group or phenoxy group ⁇ ;
  • R 12 may have one or more groups listed in the following group b-2, and in the case of two or more groups, they may be the same or different; [Substituent group b-2] ⁇ Halogen atom, A C1-C3 alkyl group, A C1-C3 hal
  • a 2 means a quinolin-6-yl group, a benzothiazol-6-yl group or a [1,5] naphthyridin-2-yl group
  • X 2 represents a group represented by the formula —C ( ⁇ O) —NH— or a group represented by the formula —NH—C ( ⁇ O) —
  • R 20, R 21, two or more of R 22 and R 23 means a substituent listed below the substituent group a-5, the remaining R 20, R 21, R 22 and R 23 represents hydrogen Means an atom; [Substituent group a-5] ⁇ Halogen atom, A C1-C3 alkyl group, A C1-C3 haloalkyl group, A C1-C3 alkoxy group, C1-C3 haloalkoxy group and cyano group ⁇ ] (Hereinafter referred to as the present amide compound).
  • a in formula (I) representing this compound is quinolin-6-yl optionally having 1 to 3 substituents listed in the following substituent group a-1 and substituent group a-2
  • the benzothiazol-6-yl group optionally having 1 to 3 substituents listed in the group a-1 and the substituent group a-2, a-1 and the substituent group a-2. It means a [1,5] naphthyridin-2-yl group optionally having 1 to 3 substituents.
  • [Substituent group a-1] ⁇ Halogen atom, hydroxyl group, mercapto group, cyano group, formyl group, carboxyl group, C1-8 alkyl group, C2-9 alkenyl group, C2-9 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5 -10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, C6-10 aryl C2-6 alkenyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C2-9 alkenyloxy group, C2-9 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5-10 member Heterocyclic oxy group, C3-8 cycloalkyl C1-6 alkoxy
  • [Substituent group b-1] ⁇ Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group Group, C1-6 alkoxy group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoromethoxy group, mono- It may have one C1-6 alkylamino group, di-C1-6 alkylamino group, one amino group or one aminosulfonyl group, one mono-C6-10 arylamino group and one amino group Good N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group ⁇ As A, quinolin-6-yl group optionally having 1
  • Y is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • halogen atom examples include a fluorine atom, a chlorine atom and a bromine atom
  • C1-6 alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an iso-butyl group, and an n-pentyl group.
  • C2-6 alkenyl groups are vinyl group, allyl group, 2-butenyl group, 3-butenyl group 2-pentenyl group, 3-pentenyl group, prenyl group, 3-methyl-3-butenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 4-methyl-4-pentenyl group and 4-methyl
  • Examples of C2-6 alkynyl groups include ethynyl, propargyl, 2-butynyl, 3-butynyl, 2-pentynyl, 3-pentynyl, 4-pentenyl
  • Examples of C3-8 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, including tinyl, 2-hexyny
  • Groups and cyclooctyl groups examples of C6-10 aryl groups include phenyl, indenyl and naphthyl groups, examples of 5-10 membered heterocyclic groups include furyl, thienyl, pyridyl, benzofuranyl.
  • C3-8 cycloalkyl C1-6 alkyl groups include cyclopropylmethyl group, cyclopropylethyl group, cyclopropylpropyl group , Cyclopropylbutyl group, cyclopropylpentyl group, Chlopropylhexyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclobutylpropyl group, cyclobutylbutyl group, cyclobutylpentyl group, cyclopentylethyl group, cyclopentylpropyl group, cyclopentylbutyl group, cyclohexylethyl group and cyclohexylpropyl group
  • heterocyclic C1-6 alkyl group examples include a furylmethyl group, a furylethyl group, a furylpropyl group, a furylbutyl group, a furylpentyl group, a furylhexyl group, a thienylethyl group, a thienylmethyl group, a thienylpropyl group, a thienylbutyl group, A thienylpentyl group and a thienylhexyl group, Examples of groups are methoxy, ethoxy, n-propyloxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy,
  • Examples of C2-6 alkenyloxy groups are vinyloxy group, allyloxy group, 1 -Methyl-2-propenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, prenyloxy group, 3-methyl-3-butenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 4-methyl-4-pentenyl group
  • Examples of the C2-6 alkynyloxy group include propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, and 3-pentynyl.
  • Examples of the C3-8 cycloalkoxy group include a cyclopropyloxy group, a cyclobutyloxy group, Group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group and cyclooctyloxy group, examples of C6-10 aryloxy group include phenoxy group and naphthoxy group, and C3-8 cycloalkyl C1-6 alkoxy group Examples of cyclopropylmethoxy group, cyclopropyl Pyrethoxy group, cyclopropylpropoxy group, cyclopropylbutoxy group, cyclopropylpentyloxy group, cyclopropylhexyloxy group, cyclobutylmethoxy group, cyclobutylethoxy group, cyclobutylpropoxy group, cyclobutylbutoxy group, cyclobutylpentyloxy group , Cyclopentylethoxy group, cycl
  • C6-10 aryl C1-6 alkoxy groups include benzyloxy group, phenethyloxy group, phenylpropyloxy group, phenyl Butyloxy group, phenylpentyloxy group, 2-methyl-4-phenylbutyloxy group, 2-methyl-5-phenylpentyloxy group, 3-methyl-5-phenyl
  • Examples of the 5-10 membered heterocyclic C1-6 alkoxy group containing a rupentyloxy group and a (2-naphthyl) ethyloxy group include a furylmethoxy group, a furylethoxy group, a furylpropyloxy group, a furylbutyloxy group, and a furylpentyl group.
  • Examples of -6 alkenylthio groups are vinyl Thio group, allylthio group, 1-methyl-2-propenylthio group, 2-butenylthio group, 3-butenylthio group, 2-pentenylthio group, 3-pentenylthio group, prenylthio group, 3-methyl-3-butenylthio group, 2-hexenylthio group, 3-hexenylthio group, 4-hexenylthio group, 4-methyl-4-pentenylthio group and 4-methyl-3-pentenylthio group, and examples of
  • -6 alkylamino groups are methylamino group, ethyl Amino group, n-propylamino group, n-butylamino group, iso-butylamino group, n-pentylamino group, iso-pentylamino group, n-hexylamino group, 4-methylpentylamino group and 3-methylpentyl
  • mono-C2-6 alkenylamino group include an allylamino group, 2-butenylamino group, 3-butenylamino group
  • Examples of mono-5-10-membered heterocyclic C1-6 alkylamino groups include furylmethylamino group, furylethylamino group, furylpropylamino group, furylbutylamino group, furylpentylamino group, furylhexylamide group, thienyl.
  • examples of di-C1-6 alkylamino groups include dimethylamino group, methylethylamino group Group, diethylamino group, methylpropylamino group and methylbutylamino group
  • examples of N-C2-6 alkenyl-N-C1-6 alkylamino group include N-allyl-N-methylamino group, N- (2 -Butenyl) -N-methylamino group and N- (3-butenyl) -N-methyl
  • Examples of N-C2-6 alkynyl-N-C1-6 alkylamino groups containing a tilamino group include N-methyl-N-propargylamino group, N- (2-butyn
  • C1-6 alkoxycarbonyl groups are , Methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, iso-propoxycarbonyl group, n-butoxycarbonyl group, iso-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentyloxycarbonyl group, iso-pentyl Oxycarbonyl group, sec
  • R 1 , R 2 , R 3 , R 4 And R 5 As a combination of: R 1 And R 3 Are the substituents listed in the following same or different substituent group a-4, and R 2 Are substituents listed in the substituent group a-3-2, and R 4 And R 5 Is a hydrogen atom; R 1 And R 4 Are substituents listed in the same or different substituent group a-4, and R 2 Are substituents listed in the substituent group a-3-2, and R 3 And R 5 Is a hydrogen atom; R 1 And R 5 Are substituents listed in the same or different substituent group a-4, and R 2 Are substituents listed in the substituent group a-3-2, and R 3 And R 4 The case where is a hydrogen atom can be mentioned.
  • [Substituent Group a-3-2] ⁇ Halogen atom A C1-C8 alkyl group, A C2-C9 alkenyl group, A C2-C9 alkynyl group, A C7-C16 aralkyl group, A C7-C16 aralkyloxy group, A C7-C16 phenoxyalkyl group, A C1-C8 alkoxy group, A C3-C9 alkynyloxy group, A C3-C9 alkenyloxy group or Phenoxy group ⁇
  • R 12 May be substituted one or more by the same or different groups listed in the following substituent group b-2.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom
  • examples of the C1-C8 alkyl group include a methyl group, an ethyl group, a propyl group,
  • a pentyl group, a hexyl group, a heptyl group and an octyl group examples include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.
  • Examples of C7-C16 phenoxyalkyl group include phenoxymethyl group, 2-phenoxyethyl group, 3- Phenoxypropyl group, 4-phenoxybutyl group, 5-phenoxypentyl group, 6-phenoxyhexyl group, 7-phenoxyheptyl group, 8-phenoxyoctyl group, 9-phenoxynonyl group and 10-phenoxydecyl group,
  • Examples of the C8 alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group and an octyloxy group
  • examples of the C3-C9 alkenyloxy group include a 2-propenyloxy group, 2 -Butenyloxy group, 3-butenyloxy group, 2- Nthenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 2-hexenyloxy group, 3-hexen
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom
  • examples of the C1-C3 alkyl group include a methyl group, an ethyl group, a 1-methylethyl group and a propyl group.
  • C1-C3 haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl and 2,2,2-trifluoroethyl groups;
  • C3-C4 cycloalkyl Examples include a cyclopropyl group and a cyclobutyl group;
  • examples of a C1-C3 alkoxy group include a methoxy group, an ethoxy group, a 1-methylethoxy group, and a propoxy group;
  • examples of a C1-C3 haloalkoxy group include fluoro Methoxy group, difluoromethoxy group, trifluoromethoxy group, 2-fluoroethoxy group and 2,2,2-trifluoro They include butoxy group;
  • examples of C3-C4 cycloalkyl group include cyclopropyl group and cyclobutyl group.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;
  • examples of the C1-C3 alkyl group include a methyl group, an ethyl group, a 1-methylethyl group, and a propyl group.
  • C1-C3 haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl and 2,2,2-trifluoroethyl groups;
  • C1-C3 alkoxy groups Examples include methoxy, ethoxy, 1-methylethoxy and propoxy groups;
  • examples of C1-C3 haloalkoxy groups include fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy and Contains 2,2,2-trifluoroethoxy group.
  • this compound the following are mentioned, for example.
  • A is a quinolin-6-yl group, a benzothiazol-6-yl group or a [1,5] naphthyridin-2-yl group
  • X is a formula —C ( ⁇ O) —NH—
  • R 2 Is a hydrogen atom, halogen atom, C1-C8 alkyl group, C2-C9 alkenyl group, C2-C9 alkynyl group, C7-C16 aralkyl group, C7-C16 aralkyloxy group, C7-C16 phenoxyalkyl group, C1-C8 alkoxy group , A substituent selected from a C3-C9 alkynyloxy group, a C3-C9 alkenyloxy group or a phenoxy group (provided that R 2 Is one group selected from a halogen atom, C1-C3 alkyl group, C1-C3 haloalkyl group, C3-C4 cycloalkyl, C1-C3 alkoxy group, C1-C3 haloalkoxy group C3-C4 cycloalkyloxy and cyano, or Two or more, and in the case of two or more, they may be the same or different), and R
  • R 11 , R 13 , R 14 And R 15 2 or more of these means the substituents listed in the substituent group a-4, and the remaining R 11 , R 13 , R 14 And R 15 Means hydrogen atom
  • An amide compound represented by In formula (II) R 12 Are any substituents listed in the substituent group e below, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 or more when is a hydrogen atom) is the same or different group selected from a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group and a cyano group.
  • R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • Substituent group e One group selected from the group consisting of a halogen atom, a C3-C4 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy group, and a cyano group, or the same or different from each other
  • a C1-C8 alkyl group having two or more,
  • Two or more C2-C9 alkenyl groups One group selected from
  • R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a benzothiazol-6-yl group and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 or more when is a hydrogen atom) is the same or different group selected from a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group and a cyano group.
  • R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a [1,5] naphthyridin-2-yl group and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 or more when is a hydrogen atom) is the same or different group selected from a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group and a cyano group.
  • R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a halogen atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a quinolin-6-yl group and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 or more when is a hydrogen atom) means the same or different halogen atoms, and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a benzothiazol-6-yl group and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 or more when is a hydrogen atom) means the same or different halogen atoms, and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a [1,5] naphthyridin-2-yl group and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 or more when is a hydrogen atom) means the same or different halogen atoms, and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a fluorine atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a quinolin-6-yl group and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a fluorine atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • R 12 3 is a hydrogen atom
  • X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is any substituent listed in the substituent group e
  • R 11 , R 13 , R 14 And R 15 2 or more of these is the same or different group selected from a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group and a cyano group.
  • R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is any substituent listed in the substituent group e
  • R 11 , R 13 , R 14 And R 15 2 or more of these is the same or different group selected from a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group and a cyano group.
  • R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is any substituent listed in the substituent group e
  • R 11 , R 13 , R 14 And R 15 2 or more of these is the same or different group selected from a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group and a cyano group.
  • R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is any substituent listed in the substituent group e
  • R 11 , R 13 , R 14 And R 15 2 or more of these is the same or different group selected from a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group and a cyano group.
  • R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is any substituent listed in the substituent group e
  • R 11 , R 13 , R 14 And R 15 2 or more of these means a halogen atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a halogen atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a halogen atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a halogen atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is any substituent listed in the substituent group e
  • R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a fluorine atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a fluorine atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a fluorine atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 Is a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is any substituent listed in the substituent group e, and R 11 , R 13 , R 14 And R 15 2 or more of these (however, R 12 3 is a hydrogen atom) means a fluorine atom and the remaining R 11 , R 13 , R 14 And R 15 Is an amide compound meaning a hydrogen atom.
  • a 1 An amide compound wherein is a quinolin-6-yl group.
  • a 1 An amide compound in which is a [1,5] naphthyridin-2-yl group.
  • X 1 An amide compound in which is a group represented by the formula —NH—C ( ⁇ O) —.
  • R 11 An amide compound in which is a fluorine atom.
  • R 11 And R 13 Is a fluorine atom and R 4 And R 5 An amide compound in which is a hydrogen atom.
  • R 11 And R 14 Is a fluorine atom and R 3 And R 5 An amide compound in which is a hydrogen atom.
  • R 11 And R 16 Is a fluorine atom and R 3 And R 4 An amide compound in which is a hydrogen atom.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 11 And R 13 Is a fluorine atom and R 14 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 11 And R 13 Is a fluorine atom and R 14 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 11 And R 13 Is a fluorine atom and R 14 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 11 And R 14 Is a fluorine atom and R 13 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 11 And R 16 Is a fluorine atom and R 13 And R 14 An amide compound in which is a hydrogen atom.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 11 And R 16 Is a fluorine atom and R 13 And R 14 An amide compound in which is a hydrogen atom.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 11 And R 16 Is a fluorine atom and R 13 And R 14 An amide compound in which is a hydrogen atom.
  • X is a group represented by the formula —NH—C ( ⁇ O) —
  • R 1 And R 3 Is a fluorine atom and R 4 And R 5
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 11 And R 13 Is a fluorine atom and R 14 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 11 And R 13 Is a fluorine atom and R 14 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 11 And R 14 Is a fluorine atom and R 13 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 11 And R 14 Is a fluorine atom and R 13 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 11 And R 14 Is a fluorine atom and R 13 And R 15 An amide compound in which is a hydrogen atom.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 11 And R 16 Is a fluorine atom and R 13 And R 14 An amide compound in which is a hydrogen atom.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C1-C8 alkyl group optionally having more than one group.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C2-C9 alkenyl group optionally having more than one group.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C2-C9 alkynyl group optionally having more than one group.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C7-C16 aralkyl group optionally having more than one group.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C7-C16 aralkyloxy group optionally having more than one group.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C7-C16 phenoxyalkyl group optionally having more than one group.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C1-C8 alkoxy group optionally having more than one group.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C3-C9 alkynyloxy group optionally having one or more groups.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • An amide compound which is a C3-C9 alkenyloxy group optionally having one or more groups.
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • R 11 An amide compound in which is a C1-C8 alkyl group.
  • R 11 An amide compound in which is a C2-C9 alkenyl group.
  • R 11 An amide compound in which is a C2-C9 alkynyl group.
  • R 11 An amide compound in which is a C7-C16 aralkyl group.
  • R 11 An amide compound in which is a C7-C16 aralkyloxy group.
  • R 11 An amide compound wherein is a C7-C16 phenoxyalkyl group.
  • R 11 An amide compound in which is a C1-C8 alkoxy group.
  • R 11 An amide compound in which is a C3-C9 alkynyloxy group.
  • R 11 Is an amide compound having a C7-C16 aralkyloxy group.
  • R 11 An amide compound wherein is a C3-C9 alkenyloxy group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 2 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 2 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • A is a quinolin-6-yl group
  • X is a group represented by the formula —C ( ⁇ O) —NH—
  • R 2 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —C ( ⁇ O) —NH—, and R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 2 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a quinolin-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Is a benzothiazol-6-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —
  • R 2 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a 1 Has a [1,5] naphthyridin-2-yl group and X 1 Is a group represented by the formula —NH—C ( ⁇ O) —, R 12 Is selected from the group consisting of a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl, a C1-C3 alkoxy group, a C1-C3 haloalkoxy group, a C3-C4 cycloalkyloxy, and a cyano group.
  • a phenoxy group optionally having more than one group, and R 11 And R 16 Is a fluorine atom and R 13 And R 14 An amide compound in which is a hydrogen atom.
  • the structural formula of a compound may represent a certain isomer for convenience, but in the present invention, all active geometric isomers, optical isomers, stereoisomers, It includes isomers such as mutants and isomer mixtures, and is not limited to the description of the formula for convenience, and either isomer or mixture may be used. Accordingly, there may be an optically active substance and a racemate having an asymmetric carbon atom in the molecule. However, the present invention is not particularly limited and includes any case. The production method of this compound will be described.
  • This compound can be produced, for example, by the following (Production Method 1), (Production Method 2), (Production Method 3) or (Production Method 4).
  • (Production method 1) the compound (I-1) in which Y in the formula (I) is an oxygen atom includes the compound (IV) and the compound (V) or a salt thereof (for example, hydrochloride and hydrobromide).
  • a dehydrating condensing agent for example, hydrochloride and hydrobromide.
  • ethers such as tetrahydrofuran (hereinafter sometimes referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether (hereinafter sometimes referred to as MTBE), hexane, heptane, and the like.
  • Aliphatic hydrocarbons such as octane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, N, N- Examples include acid amides such as dimethylformamide (hereinafter sometimes referred to as DMF), sulfoxides such as dimethyl sulfoxide (hereinafter sometimes referred to as DMSO), and nitrogen-containing aromatic compounds such as pyridine. Each of these may be used alone or mixed with one or more other It may be used Te.
  • DMF dimethylformamide
  • DMSO dimethyl sulfoxide
  • pyridine nitrogen-containing aromatic compounds
  • Examples of the dehydrating condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC), carbodiimides such as 1,3-dicyclohexylcarbodiimide, (benzotriazole) -1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (hereinafter sometimes referred to as BOP reagent) and the like.
  • WSC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride
  • carbodiimides such as 1,3-dicyclohexylcarbodiimide, (benzotriazole) -1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (hereinafter sometimes referred to as BOP reagent) and the like.
  • the reaction temperature is usually ⁇ 20 ° C. to 140 ° C., and the reaction time is usually 1 to 24 hours.
  • the compound (I-1) can be isolated by filtration. If no solid is precipitated, the reaction mixture is dissolved in an organic solvent.
  • the compound (I-1) can be isolated by performing post-treatment operations such as extraction with, and drying and concentration of the organic layer.
  • the isolated compound (I-1) can be further purified by chromatography, recrystallization and the like.
  • Y in formula (I) is an oxygen atom (I-1) includes compound (VI) and compound (V) or a salt thereof (for example, hydrochloride and hydrobromide).
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogenation such as chlorobenzene.
  • Examples include hydrocarbons, esters such as butyl acetate and ethyl acetate, and nitriles such as acetonitrile, each of which may be used alone or in combination with one or more other. Also good.
  • Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. .
  • the amount of compound (V) used is usually 0.5-1 mol and the amount of base used is usually 1-5 mol with respect to 1 mol of compound (VI).
  • the reaction temperature is usually ⁇ 20 to 100 ° C., and the reaction time is usually 0.1 to 24 hours.
  • the compound (I-1) can be isolated by filtration. If no solid is precipitated, the reaction mixture is dissolved in an organic solvent.
  • the present amide compound can be isolated by performing post-treatment operations such as extraction with, and drying and concentration of the organic layer.
  • the isolated compound (I-1) can be further purified by chromatography, recrystallization and the like.
  • the compound (I-2) in which Y in the formula (I) is a sulfur atom is the same as the compound (I-1) in which Y in the formula (I) is an oxygen atom and 2,4- It can be produced by reacting bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetane-2,4-disulfide (a compound generally known as Lawesson's reagent). [In the formula, A, R 1 , R 2 , R 3 , R 4 And R 5 Represents the same meaning as described above. ] The reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction examples include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether, aliphatic hydrocarbons such as hexane, heptane, and octane, and aromatics such as toluene and xylene.
  • ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and tert-butyl methyl ether
  • aliphatic hydrocarbons such as hexane, heptane, and octane
  • aromatics such as toluene and xylene.
  • Group hydrocarbons, halogenated hydrocarbons such as chlorobenzene, nitriles such as acetonitrile and butyronitrile, and sulfoxides such as dimethyl sulfoxide, each of which may
  • the amount of Lawesson's reagent to be used is generally 1 to 10 mol per 1 mol of compound (I-1).
  • the reaction temperature is usually 50 to 150 ° C., and the reaction time is usually 0.5 to 24 hours.
  • the compound (I-2) can be isolated by performing post-treatment operations such as pouring water into the reaction mixture to extract it with an organic solvent, and drying and concentrating the organic layer.
  • the isolated compound (I-2) can be further purified by operations such as chromatography and recrystallization.
  • R in formula (I) 2 Compound (I-3) in which is a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C3-C10 cycloalkyl group, a C7-C16 aralkyl group, etc. ) In the presence of a base.
  • R 6 Represents a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a C3-C10 cycloalkyl group, a C7-C16 aralkyl group, etc.
  • L is a bromine atom, an iodine atom, a methanesulfonyloxy group, trifluoromethane A sulfonyloxy group or a p-toluenesulfonyloxy group is represented.
  • the reaction is usually performed in the presence of a solvent.
  • Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, nitriles such as acetonitrile, and DMF.
  • ethers such as THF, ethylene glycol dimethyl ether, and MTBE
  • aromatic hydrocarbons such as toluene and xylene
  • halogenated hydrocarbons such as chlorobenzene
  • nitriles such as acetonitrile
  • DMF DMF
  • Examples include acid amides, sulfoxides such as dimethyl sulfoxide, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, and water, each of which may be used alone or mixed with one or more other types. May be used.
  • Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydroxides such as sodium hydroxide, alkali metal hydrides such as sodium hydride, and the like.
  • the amount of compound (VIII) used is usually 1 to 10 moles and the amount of base used is usually 1 to 5 moles relative to 1 mole of compound (VII).
  • the reaction temperature is usually ⁇ 20 to 100 ° C., and the reaction time is usually 0.1 to 24 hours. After completion of the reaction, when solid is precipitated after adding water, the compound (I-3) can be isolated by filtration, and when no solid is precipitated, the reaction mixture is dissolved in an organic solvent.
  • the compound (I-3) can be isolated by performing post-treatment operations such as extraction with, and drying and concentration of the organic layer.
  • the isolated compound (I-3) can be further purified by chromatography, recrystallization and the like.
  • the present amide compound can be produced, for example, by the following (Synthesis Method 1) or (Synthesis Method 2).
  • Synthesis method 1 Among the amide compounds, X in the formula (III) 1 Is a group represented by the formula —C ( ⁇ O) —NH—, compound (IX) and compound (X) or a salt thereof (for example, hydrochloride and hydrobromide are Can be reacted in the presence of a dehydration condensing agent.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogenation such as chlorobenzene.
  • Examples include hydrocarbons, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as DMF, sulfoxides such as DMSO, and nitrogen-containing aromatic compounds such as pyridine. Each of these may be used alone or in combination with one or more other.
  • Examples of the dehydrating condensing agent used in the reaction include WSC and carbodiimides such as 1,3-dicyclohexylcarbodiimide, BOP reagent and the like.
  • the amount of compound (X) used is usually 0.5-3 mol and the amount of dehydrating condensing agent used is usually 1-5 mol with respect to 1 mol of compound (X).
  • the reaction temperature is usually ⁇ 20 ° C. to 140 ° C., and the reaction time is usually 1 to 24 hours.
  • the compound (III-1) can be isolated by filtration, and when the solid does not precipitate, the reaction mixture is dissolved in an organic solvent.
  • the compound (III-1) can be isolated by performing post-treatment operations such as extraction with, and drying and concentration of the organic layer.
  • the isolated compound (III-1) can be further purified by chromatography, recrystallization and the like.
  • Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogenation such as chlorobenzene.
  • ethers such as THF, ethylene glycol dimethyl ether, and MTBE
  • aliphatic hydrocarbons such as hexane, heptane, and octane
  • aromatic hydrocarbons such as toluene and xylene
  • halogenation such as chlorobenzene
  • Examples include hydrocarbons, esters such as butyl acetate and ethyl acetate, and nitriles such as acetonitrile, each of which may be used alone or in combination with one or more other. Also good.
  • Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. It is done.
  • the amount of compound (X) used is usually 0.5-1 mol and the amount of base used is usually 1-5 mol with respect to 1 mol of compound (XI).
  • the reaction temperature is usually ⁇ 20 to 100 ° C., and the reaction time is usually 0.1 to 24 hours.
  • the compound (III-1) can be isolated by filtration, and when the solid does not precipitate, the reaction mixture is dissolved in an organic solvent.
  • the compound (III-1) can be isolated by performing post-treatment operations such as extraction with, and drying and concentration of the organic layer.
  • the isolated compound (III-1) can be further purified by chromatography, recrystallization and the like. Specific examples of the compound include the following compounds.
  • the control agent of the present invention is prepared by mixing the present compound with a solid carrier, liquid carrier, gas carrier, surfactant, etc., and optionally adding adjuvants for preparation such as a fixing agent, a dispersing agent, a stabilizer, etc.
  • the solid carrier examples include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon
  • the liquid carrier examples include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like.
  • Hydrogens eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene
  • aliphatic hydrocarbons eg, n-hexane, cyclohexanone, kerosene
  • esters eg, ethyl acetate, butyl acetate
  • nitriles eg, , Acetonitrile, isobutylnitrile
  • ethers eg , Dioxane, diisopropyl ether
  • acid amides e.g., dimethylformamide, dimethylacetamide
  • halogenated hydrocarbons e.g., dichloroethane, trichlorethylene, and carbon tetrachloride
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.
  • formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.
  • fixing agents and dispersants specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for
  • control agent of the present invention is not particularly limited as long as the control agent of the present invention can be applied substantially, but for example, treatment to plant bodies such as foliage spraying, plant such as soil treatment, etc. And the like, and the treatment of seeds such as seed disinfection.
  • present control agent may be used simultaneously with or without mixing with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers or soil conditioners. You can also.
  • Such other fungicides include, for example, propiconazole, prothioconazole, triazimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumi Azole fungicides such as sol, tetraconazole, microbutanyl, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, vitertanol, imazalyl, flutriahol; fenpropimorph, tridemorph, fenpropidin, etc.
  • Cyclic amine bactericidal compounds benzimidazole bactericidal compounds such as carbendazim, benomyl, thiabendazole, thiophanate methyl; procymidone; ciprodini Pyrimethanyl; Dietofencarb; Thiuram; Fluazinam; Mancozeb; Iprodione; Vinclozoline; Chlorotalonyl; Captan; Mepanipyrim; Fenpiclonyl; Fludioxonil; Xylostrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyphene; fenhexamide; famoxadone; fenamidone; zoxamide; ethaboxam; Metolaphenone; fluopyran; bixafen; cyflufenamide and Kinajido and the like.
  • the application amount of the control agent of the present invention varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc.
  • the amount is 1 to 500 g, preferably 2 to 200 g.
  • Emulsions, wettable powders, suspending agents and the like are usually diluted with water and applied.
  • the concentration of the compound after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to 1% by weight.
  • the powder, granules and the like are usually applied as they are without dilution.
  • the amount of the present compound in the control agent of the present invention is usually 0.001 to 100 g, preferably 0.01 to 50 g per 1 kg seed.
  • the control agent of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards.
  • the control agent of the present invention can control diseases of the farmland in the farmland where the following “crop” and the like are cultivated.
  • Agricultural crops corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplants, tomatoes, peppers, peppers, potatoes) Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae (burdock, Shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, red pepper, etc.), red crustacean vegetables (spinach, chard, etc.) (Perilla, mint, basil ), Strawberry, sweet potato, yam, taro, etc., Bridegroom, Foliage plant, Fruit trees;
  • Trees other than fruit trees Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.
  • Biofuel plants Jatropha curcas, safflower, Amanas, switchgrass, Miss Kansas, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors glutamine synthase inhibitors
  • herbicides such as bromoxynil
  • imidazoline non-herbicide-resistant Clearfield canola
  • imazetapir imidazoline non-herbicide-resistant Clearfield
  • sulfonylurea-type ALS-inhibiting herbicide-resistant such as thifensulfuron methyl
  • STS soybeans Examples of “crop” to which tolerance has been imparted by genetic recombination technology include glyphosate and glufosinate-resistant corn varieties, which are already sold under trade names such as RoundupReady (registered trademark) and LibertyLink (registered trademark). Has been.
  • the “crop” includes, for example, a crop that can synthesize selective toxins known in the genus Bacillus by using genetic recombination technology.
  • Toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popirie; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Insecticidal proteins such as ⁇ -endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plants Lectin; agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; ly
  • Ribosome inactivating protein RIP
  • steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-COA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
  • toxins expressed in such genetically modified crops hybrids of insecticidal proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, and the like, ⁇ -endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A Toxins, partially defective toxins, modified toxins are also included.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073, and the like.
  • the toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.
  • genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known and some are commercially available.
  • transgenic plants examples include YieldGard® (a corn variety that expresses Cry1Ab toxin), YieldGuard Rootworm® (a corn variety that expresses Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1) Corn varieties expressing toxin), Herculex I® (corn varieties expressing phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties that express), Bollgard I (registered trademark) (cotton varieties that express Cry1Ac toxin), Bollgard II (registered trademark) (Cry1Ac and cotton varieties expressing ry2Ab toxin), VIPCOT® (cotton varieties expressing VIP toxin), NewLeaf® (potato varieties expressing Cry3A toxin), NatureGard® Agriure® Examples include GT Advantage (GA
  • the above “crop” includes those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
  • PR proteins and the like are known as examples of anti-pathogenic substances (PRPs, EP-A-0 392 225).
  • anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191 and the like.
  • anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.).
  • Ion channel inhibitors Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; PR protein; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes, WO 03/000906)) and the like, and the like, and the like, and the like, which are produced by microorganisms.
  • plant diseases that can be controlled by the present invention include filamentous fungi and the like, and more specifically, the following diseases can be mentioned, but are not limited thereto.
  • this invention control method is performed by using this invention control agent by the method of applying this invention control agent mentioned above.
  • Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuri); Wheat powdery mildew (Erysiphe graminis), red mold (Fusarium graminearum, F. avenacerum, F. culmorum, Microchium nivare), rust (Puccinia striformis, P. ra. Rot disease (Typhula sp., Microlectriella nivalis), Bare smut (Ustilago tritici, U.
  • Apple monilia disease Valsa ceratosperma
  • powdery mildew Podosphaera leucotrica
  • spotted leaf disease Alternaria alternata apple disease
  • black spot disease Alternaria alternata apple disease
  • Pear black spot Venturia nashicola, V.
  • Green Bean Anthracnose (Colletotrichum lindemthianum) Peanut black astringency (Cercospora personata), brown spot (Cercospora arachidicola), white silkworm (Sclerotium rolfsii); Pea powdery mildew (Erysiphe pisi); Potato summer plague (Alternaria solani), plague (Phytophthora infestans), half body wilt (Verticillium albo-atrum, V. dahlliae, V.
  • Production Example 17 A mixture of 0.20 g of N- (2,4-difluoro-3-hydroxyphenyl) methyl-quinoline-6-carboxylic acid amide, 0.21 g of 4-ethoxybutyl-p-toluenesulfonate and 3 ml of DMF was added with 0.31 g of cesium carbonate. And stirred at room temperature for 10 hours.
  • Synthesis example 1 Quinoline-6-carboxylic acid 9.7 g, 2,4-difluoro-3-hydroxybenzylamine hydrochloride 7.1 g, WSC 9.5 g, pyridine 13 ml and DMF 150 ml were mixed and stirred at room temperature for 6 hours. Thereafter, water was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Water and ethyl acetate were added to the obtained residue, the solid was filtered off, washed with hexane, dried under reduced pressure, and N- (2,4-difluoro-3-hydroxyphenyl) methyl-quinoline-6-carboxylic acid.
  • Synthesis example 2 0.65 g of WSC was added to a mixture of 0.51 g of 6-quinolinecarboxylic acid, 0.72 g of 2,5-difluoro-3-hydroxybenzylamine hydrobromide and 10 ml of pyridine, and the mixture was stirred at room temperature for 12 hours. Thereafter, water was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with ethyl acetate.
  • Reference production example 1 2.8 g of 2,6-difluoroanisole, 3.7 g of N, N, N ′, N ′′, N ′′ -pentamethyldiethylenetriamine and 50 ml of THF were mixed, and 1.6 mol / liter of n-butyllithium at ⁇ 70 ° C. 12 ml of hexane solution was mixed and stirred at ⁇ 70 ° C. for 1 hour. After mixing dry ice with the mixture, the temperature was gradually raised to room temperature.
  • the obtained residue (acid chloride) was mixed with THF, added to a mixture of 28% aqueous ammonia 5 ml and THF 50 ml, and stirred at room temperature for 15 minutes.
  • the reaction mixture was concentrated under reduced pressure, water was added, and this was extracted with ethyl acetate.
  • the organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to obtain a solid. Drying under reduced pressure gave 2.4 g of 2,4-difluoro-3-methoxybenzamide.
  • Reference production example 4 27 g of 2,6-difluorophenol, 38 g of 2-iodopropane, 150 ml of DMF, 300 ml of acetonitrile and 42 g of potassium carbonate were stirred at room temperature for 6 hours. Ethyl acetate was added to the reaction mixture, the precipitated solid was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was mixed with MTBE, washed successively with 5% hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give 2,6-difluoro- 36 g of 2-isopropoxybenzene was obtained.
  • the obtained residue (acid chloride) was mixed with toluene, added to a mixture of 28% aqueous ammonia 87 ml and THF 500 ml, and stirred at room temperature for 15 minutes.
  • the reaction mixture was concentrated under reduced pressure, water was added, and this was extracted with ethyl acetate.
  • the obtained organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure.
  • the obtained solid was dried under reduced pressure to obtain 30 g of 2,4-difluoro-3-isopropoxybenzamide.
  • the obtained organic layer was washed with saturated brine, dried over potassium carbonate, and concentrated under reduced pressure to obtain 29 g of 2,4-difluoro-3-isopropoxybenzylamine.
  • the obtained 2,4-difluoro-3-isopropoxybenzylamine (28 g) and 36% hydrochloric acid (59 ml) were mixed and stirred at 100 ° C. for 5 hours.
  • the reaction mixture allowed to cool to near room temperature was concentrated under reduced pressure, hexane was added, and the solid was filtered off.
  • the obtained solid was washed with acetonitrile and hexane, and then dried under reduced pressure to obtain 23 g of 2,4-difluoro-3-hydroxybenzylamine hydrochloride.
  • Reference production example 8 A mixture of 1.39 g of sodium borohydride and 30 ml of tetrahydrofuran was cooled to 0 ° C., and 4.21 g of trifluoroacetic acid was added dropwise. Next, a mixture of 1.5 g of the 2,5-difluoro-3-methoxybenzaldehyde-O-methyl-oxime isomer mixture obtained in Reference Production Example 7 and 3 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at 0 ° C. for 10 minutes. Heated to reflux for 30 minutes. Water was added to the reaction mixture which had been allowed to cool to near room temperature, and this was extracted with tert-butyl methyl ether.
  • Reference production example 10 13 g of 2,4-difluoro-3-methoxybenzene and 200 ml of THF were mixed, 80 ml of a mixed solution of about 2 mol / liter of lithium diisopropylamide in THF, ethylbenzene and heptane was added at -70 ° C, and the mixture was stirred at -70 ° C for 30 minutes. The mixture was mixed with 35 ml DMF and stirred at -70 ° C for 30 minutes and then at room temperature for 1 hour. Saturated aqueous ammonium chloride was added to the reaction mixture, and this was extracted with ethyl acetate.
  • the obtained organic layer was washed successively with 5% hydrochloric acid, water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to obtain a crude product of 2,4-difluoro-3-methoxybenzaldehyde.
  • a mixture of crude 2,4-difluoro-3-methoxybenzaldehyde, 200 ml of methanol and 3.1 g of sodium borohydride was stirred at room temperature for 1 hour. Water and 5% hydrochloric acid were added to the reaction mixture, and the mixture was concentrated under reduced pressure and extracted with ethyl acetate.
  • the obtained organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure.
  • the reaction mixture was concentrated under reduced pressure to obtain a crude product of 1-chloromethyl-2,4-difluoro-3-methoxybenzene.
  • the obtained crude product of 1-chloromethyl-2,4-difluoro-3-methoxybenzene, 0.91 g of sodium cyanide and 15 ml of DMSO were mixed and stirred at room temperature for 6 hours.
  • Water was added to the reaction mixture, which was extracted 3 times with MTBE.
  • the obtained organic layer was washed successively with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure.
  • the obtained residue was subjected to silica gel column chromatography to obtain 2.4 g of 2,4-difluoro-3-methoxyphenylethanenitrile.
  • Formulation Example 1 50 parts of each of the present compounds (1) to (36), 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide are thoroughly pulverized and mixed to obtain a wettable powder.
  • Formulation Example 2 After 20 parts of each of the present compounds (1) to (36) and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and pulverized by a wet pulverization method.
  • Formulation Example 3 By thoroughly pulverizing and mixing 2 parts of each of the present compounds (1) to (36), 88 parts of kaolin clay and 10 parts of talc, a powder is obtained.
  • Formulation Example 4 Emulsions are obtained by thoroughly mixing 5 parts of each of the present compounds (1) to (36), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
  • Formulation Example 5 2 parts of each of the present compounds (1) to (36), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, and then kneaded well with water, Granules are obtained by granulating and drying.
  • Formulation Example 6 This compound (1) to (36) is mixed with 10 parts of each, 35 parts of white carbon containing 50 parts of a polyoxyethylene alkyl ether sulfate ammonium salt and 55 parts of water, and finely pulverized by a wet pulverization method to obtain a flowable preparation. obtain.
  • test examples show that the control agent of the present invention is useful for controlling plant diseases.
  • the control effect is to visually observe the area of the lesion on the test plant at the time of the survey, and to compare the area of the lesion on the plant treated with the present control agent and the area of the lesion on the untreated plant. It was evaluated by.
  • Test example 1 Cucumber gray mold prevention effect test (Botrytis cinerea) A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days.
  • Each of the present compounds (1), (3), (4), (13), (15) to (18), (20), (23) to (29), (31) and (33) is a formulation example. After making a flowable formulation according to No.
  • the lesion area in the treated plant was 10% or less of the lesion area in the untreated plant.
  • Test example 2 Cucumber nuclear disease prevention effect test (Sclerotinia sclerotiorum) A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. Each of the present compounds (1) to (33) and (34) was made into a flowable preparation according to Preparation Example 6 and then diluted with water to a predetermined concentration (500 ppm), so that the foliage was sufficiently adhered to the cucumber leaf surface. Scattered. After spraying, the plants were air-dried, and a mycelia-containing PDA medium containing mycorrhizal fungi was placed on the cucumber leaf surface. After the inoculation, the lesion area was examined after being placed at 18 ° C.
  • Test example 4 Test for prevention of kidney bean nuclear disease (Sclerotinia sclerotiorum) A plastic pot was stuffed with sand loam, seeded with green beans (variety; Nagatake peas) and grown in a greenhouse for 8 days.
  • the compound (36) was made into a flowable formulation according to Formulation Example 6, then diluted with water to a predetermined concentration (500 ppm), and sprayed on the foliage so as to adhere well to the kidney beans. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of kidney bean sclerotia was placed on the bean leaf surface. After the inoculation, all kidney beans were left under high humidity only at night, and the lesion area was examined 5 days after the inoculation. As a result, the lesion area in the plant treated with the compound (36) was 30% or less of the lesion area in the untreated plant.
  • Test Example 5 Barley net spot disease prevention effect test (Pyrenophora teres) A plastic pot was filled with sand loam, sown with barley (variety: Nishinohoshi), and grown in a greenhouse for 10 days. Compounds (35) and (36) were made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed on the foliage so as to adhere well to the leaves of the barley. After spraying, the plants were air-dried, and after 2 days, sprayed with a water suspension of barley reticular fungus spores. After inoculation, it was placed at 20-23 ° C. and high humidity for 3 days and then placed in a greenhouse for 7 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compounds (35) and (36) was 30% or less of the lesion area in the untreated plant.
  • the plant disease can be controlled with the control agent of the present invention.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Quinoline Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Cette invention concerne un agent de contrôle phytosanitaire contenant un composé de formule (I) pour principe actif et doté d'une excellente activité de lutte contre les maladies des plantes. (Dans la formule, A représente un groupe quinolin-6-yle, un groupe benzothiazol-6-yle ou un groupe [1,5]naphthyridin-2-yle ; X représente un groupe exprimé par -C(=Y)-NH- ou un groupe exprimé par -NH-C(=Y)- ; Y représente un atome d'oxygène, un atome de soufre ou NRY (RY représentant un groupe alcoxy en C1-6 ou un groupe cyano) ; et R1, R2, R3, R4 et R5 sont tels que définis dans la description.)
PCT/JP2009/066868 2008-09-19 2009-09-18 Agent de contrôle phytosanitaire Ceased WO2010032881A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2008-240758 2008-09-19
JP2008240758 2008-09-19

Publications (1)

Publication Number Publication Date
WO2010032881A1 true WO2010032881A1 (fr) 2010-03-25

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2009/066868 Ceased WO2010032881A1 (fr) 2008-09-19 2009-09-18 Agent de contrôle phytosanitaire

Country Status (2)

Country Link
JP (1) JP2010095520A (fr)
WO (1) WO2010032881A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102464612A (zh) * 2010-11-19 2012-05-23 中国中化股份有限公司 含哌嗪氨基甲酸酯的二卤丙烯醚类化合物与应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005033079A1 (fr) * 2003-09-30 2005-04-14 Eisai Co., Ltd. Agent antifongique a compose heterocyclique
WO2008050199A2 (fr) * 2006-10-23 2008-05-02 Pfizer Japan Inc. Composés de phénylméthyl bicyclocarboxyamide substitués
WO2009009637A1 (fr) * 2007-07-12 2009-01-15 Buckman Laboratories International, Inc. Compositions de fabrication de papier et procédés utilisant une particule de protéine, un pigment colloïdal et des combinaisons de polymère de latex
JP2009108021A (ja) * 2007-03-22 2009-05-21 Sumitomo Chemical Co Ltd 植物病原菌による植物病害を防除又は予防するための農業用組成物
JP2009120587A (ja) * 2007-10-23 2009-06-04 Sumitomo Chemical Co Ltd アミド化合物及びその用途

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005033079A1 (fr) * 2003-09-30 2005-04-14 Eisai Co., Ltd. Agent antifongique a compose heterocyclique
WO2008050199A2 (fr) * 2006-10-23 2008-05-02 Pfizer Japan Inc. Composés de phénylméthyl bicyclocarboxyamide substitués
JP2009108021A (ja) * 2007-03-22 2009-05-21 Sumitomo Chemical Co Ltd 植物病原菌による植物病害を防除又は予防するための農業用組成物
WO2009009637A1 (fr) * 2007-07-12 2009-01-15 Buckman Laboratories International, Inc. Compositions de fabrication de papier et procédés utilisant une particule de protéine, un pigment colloïdal et des combinaisons de polymère de latex
JP2009120587A (ja) * 2007-10-23 2009-06-04 Sumitomo Chemical Co Ltd アミド化合物及びその用途

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102464612A (zh) * 2010-11-19 2012-05-23 中国中化股份有限公司 含哌嗪氨基甲酸酯的二卤丙烯醚类化合物与应用
CN102464612B (zh) * 2010-11-19 2014-12-24 中国中化股份有限公司 含哌嗪氨基甲酸酯的二卤丙烯醚类化合物与应用

Also Published As

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