WO2017146220A1 - Composé de quinoléine présentant un hétérocycle condensé lié à celui-ci, n-oxyde ou sels correspondants et insecticide agricole et horticole contenant le composé et procédé pour son utilisation - Google Patents

Composé de quinoléine présentant un hétérocycle condensé lié à celui-ci, n-oxyde ou sels correspondants et insecticide agricole et horticole contenant le composé et procédé pour son utilisation Download PDF

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WO2017146220A1
WO2017146220A1 PCT/JP2017/007161 JP2017007161W WO2017146220A1 WO 2017146220 A1 WO2017146220 A1 WO 2017146220A1 JP 2017007161 W JP2017007161 W JP 2017007161W WO 2017146220 A1 WO2017146220 A1 WO 2017146220A1
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group
halo
oxide
atom
general formula
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直登 清水
樹 米村
勇介 佐野
千明 山内
悠司 櫻井
諏訪　明之
隼平 藤江
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Nihon Nohyaku Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to an agricultural and horticultural insecticide containing, as an active ingredient, a quinoline compound, N-oxide or a salt thereof to which a fused heterocycle is bonded, and a method of using the same.
  • Patent Documents 1 to 7 Such documents do not disclose quinoline compounds to which fused heterocycles are bonded.
  • R 2 represents (b1) halogen atom; (b2) cyano group; (b3) nitro group; (b4) (C 1 -C 6 ) alkyl group; (b5) (C 3 -C 6 ) cycloalkyl group; b6) (C 1 -C 6) alkoxy group; (b7) (C 2 -C 6) alkenyloxy group; (b8) (C 2 -C 6) alkynyloxy group; (b9) halo (C 1 -C 6 (B10) halo (C 1 -C 6 ) alkoxy group; (b11) (C 1 -C 6 ) alkylthio group; (b12) (C 1 -C 6 ) alkylsulfinyl group; (b13) (C 1- C 6 ) alkylsulfonyl group; (b14) halo (C 1 -C 6 ) alkylthio group; (b15) halo (C 1 -C 6
  • B 1 , B 2 , B 3 , B 4 , B 5 and B 6 may be the same or different, and C—R 4 (R 4 is (d1) a hydrogen atom; (d2) a halogen atom; (d3) cyano.
  • n 0; 1; or 2; ⁇ , A quinoline compound having a condensed heterocyclic ring attached thereto, N-oxide or a salt thereof, [2]
  • B 1 , B 2 , B 3 , B 4 and B 5 are C—R 4 (R 4 is the same as above), and B 6 is a nitrogen atom.
  • R 4 is (d1) a hydrogen atom; (d2) a halogen atom; (d6) a (C 1 -C 6 ) alkoxy group; (d8) a halo (C 1 -C 6 ) alkyl group; or (d10) A quinoline compound, an N-oxide or a salt thereof, to which the condensed heterocyclic ring according to [3], which is a (C 1 -C 6 ) alkylthio group, [5] R 2 is (b9) a halo (C 1 -C 6 ) alkyl group; (b10) a halo (C 1 -C 6 ) alkoxy group;
  • R 4 is (d1) a hydrogen atom; (d2) a halogen atom; (d6) a (C 1 -C 6 ) alkoxy group; (d8) a halo (C 1 -C 6 ) alkyl group; or (d10)
  • a (C 1 -C 6 ) alkylthio group A 1 is N—R 3 (R 3 is the same as above), A 2 is a nitrogen atom, and A 3 is CH [ 1] or [2], a quinoline compound to which the condensed heterocyclic ring is bound, N-oxide or a salt thereof, [8] B 2 , B 3 , B 4 , B 5 and B 6 are C—R 4 (R 4 is (d1) a hydrogen atom; (d2) a halogen atom; (d6) (C 1 -C 6 ) An alkoxy group; (d8) a halo (C 1 -C 6 ) alkyl group; or (d10) (showing a C 1
  • B 1 , B 2 , B 3 , B 4 , B 5 and B 6 may be the same or different, and C—R 4 (where R 4 is (d1) a hydrogen atom; (d2) a halogen atom; (d3 ) Cyano group; (d4) formyl group; (d5) (C 1 -C 6 ) alkyl group; (d6) (C 1 -C 6 ) alkoxy group; (d7) (C 3 -C 6 ) cycloalkyl group; (d8) halo (C 1 -C 6 ) alkyl group; (d9) halo (C 1 -C 6 ) alkoxy group; (d10) (C 1 -C 6 ) alkylthio group; (d11) (C 1 -C 6 (D12) halo (C 1 -C 6 ) alkylthio group; (d14) halo (C 1 -C 6 ) alkylsulfinyl group; (d15)
  • a quinoline compound to which a condensed heterocyclic ring represented by [13] The condensed complex according to [12], wherein B 1 , B 2 , B 3 , B 4 , and B 5 are C—R 4 (R 4 is the same as above), and B 6 is a nitrogen atom.
  • a quinoline compound having a ring attached thereto, [14] The compound to which the fused heterocycle according to [12] is bonded, wherein B 1 , B 2 , B 3 , B 4 , B 5 and B 6 are CR 4 (R 4 is the same as above).
  • B 1 , B 2 , B 3 , B 4 , B 5 are C—R 4 (R 4 is (d1) a hydrogen atom; (d2) a halogen atom; (d6) (C 1 -C 6 ) alkoxy A group; (d8) a halo (C 1 -C 6 ) alkyl group; or (d10) (C 1 -C 6 ) an alkylthio group; and B 6 is a nitrogen atom, and A 1 is A quinoline compound to which the condensed heterocyclic ring according to [12] is an oxygen atom, and A 2 and A 3 are CH groups, [16] B 1 , B 2 , B 3 , B 4 , B 5 are CR 4 (R 4 is (d1) a hydrogen atom; (d2) a halogen atom; (d6) (C 1 -C 6 ) An alkoxy group; (d8) a halo (C 1 -C 6 ) alkyl group; or (
  • the quinoline compound or salt thereof to which the fused heterocycle of the present invention is bonded not only has an excellent effect as an agricultural and horticultural insecticide, but also parasitizes pets such as dogs and cats other than humans, and domestic animals such as cattle and sheep. Also effective against pests.
  • halo means “halogen atom” and represents chlorine atom, bromine atom, iodine atom or Indicates a fluorine atom.
  • (C 1 -C 6 ) alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group Group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group A linear or branched alkyl group having 1 to 6 carbon atoms such as 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, etc. Show.
  • (C 3 -C 6 ) cycloalkyl group refers to a cyclic alkyl group having 3 to 6 carbon atoms such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like
  • “(C 1 —C 6 ) alkoxy group ” means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary Lipentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethyl Linear or branched C1-6 alkyl such as prop
  • (C 1 -C 6 ) alkylthio group means, for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group Group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group , 1,1,2-trimethylpropylthio group or the like, which is a linear or branched alkylthio group having 1 to 6 carbon atoms, and “(C 1 -C 6 ) alkylsulfinyl group” means, for example, Methylsulfinyl
  • alkyl sulfinyl group a "(C 1 -C 6) alkylsulfonyl group", for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, nor Rubutylsulfonyl group, secondary butylsulfonyl group, tertiary butylsulfonyl group, normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropyl Linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms such as sulfonyl group, 1-methylbutylsulfon
  • (C 1 -C 6 ) alkylcarbonyl group means, for example, acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, An alkylcarbonyl group having the above (C 1 -C 6 ) alkyl group such as a pivaloyl group, a hexanoyl group, a cyclopropylcarbonyl group, etc., that is, an alkylcarbonyl group having 2 to 7 carbon atoms.
  • the “(C 1 -C 6 ) alkoxycarbonyl group” means, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, An alkoxycarbonyl group having the above-mentioned (C 1 -C 6 ) alkoxy group such as a tertiary butoxycarbonyl group or a pentyloxycarbonyl group, that is, an alkoxycarbonyl group having 2 to 7 carbon atoms.
  • “(C 1 -C 6 ) alkyl group”, “(C 3 -C 6 ) cycloalkyl group”, “(C 1 -C 6 ) alkoxy group”, “(C 2 -C 6 ) alkenyloxy group” , “(C 2 -C 6 ) alkynyloxy group”, “(C 1 -C 6 ) alkylthio group”, “(C 1 -C 6 ) alkylsulfinyl group”, “(C 1 -C 6 ) alkylsulfonyl group” ”,“ (C 1 -C 6 ) alkylcarbonyl group ”or“ (C 1 -C 6 ) alkoxycarbonyl group ” may be substituted with 1 or 2 or more halogen atoms. When two or more halogen atoms are present, the halogen atoms may be the same or different.
  • halogen atom-substituted groups are “halo (C 1 -C 6 ) alkyl group”, “halo (C 3 -C 6 ) cycloalkyl group”, “halo (C 1 -C 6 ) alkoxy group”, respectively.
  • Expressions such as “(C 1 -C 6 )”, “(C 2 -C 6 )”, “(C 3 -C 6 )” indicate the range of the number of carbon atoms of various substituents. Further, the above definition can be given for a group to which the above substituent is linked. For example, in the case of “(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group”, it is linear or branched. It indicates that an alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.
  • Examples of the quinoline compound or N-oxide salt to which the condensed heterocyclic ring represented by the general formula (1) of the present invention is bonded include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, and acetate. , Organic acid salts such as fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, inorganic or organic such as sodium ion, potassium ion, calcium ion, trimethylammonium Examples of such salts with bases.
  • inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, and acetate.
  • Organic acid salts such as fumarate, maleate, oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, inorganic or organic such as
  • the quinoline compound, N-oxide or salt thereof to which the condensed heterocyclic ring represented by the general formula (1) of the present invention is bonded may have one or more asymmetric centers in the structural formula. More than one kind of optical isomers and diastereomers may exist, and the present invention includes all of the optical isomers and a mixture containing them in an arbitrary ratio.
  • the quinoline compound, N-oxide or salt thereof to which the condensed heterocyclic ring represented by the general formula (1) of the present invention is bonded has two geometric isomerisms derived from the carbon-carbon double bond in the structural formula.
  • the present invention may exist, the present invention includes all the geometric isomers and a mixture in which they are contained in an arbitrary ratio.
  • B 1 , B 2 , B 3 , B 4 and B 5 are C— R 4 (R 4 is (d1) a hydrogen atom; (d2) a halogen atom; (d6) (C 1 -C 6 ) alkoxy group; (d8) a halo (C 1 -C 6 ) alkyl group; or (d10) (C 1 -C 6 ) represents an alkylthio group.), B 6 is a nitrogen atom, A 1 is an oxygen atom, and A 2 and A 3 are CH.
  • R 2 is (b9) a halo (C 1 -C 6 ) alkyl group; (b10) a halo (C 1 -C 6 ) alkoxy group; (b14) a halo (C 1 -C 6 ) alkylthio group; (b15) a halo (C 1 -C 6 ) alkylsulfinyl group; or (b16) a halo (C 1 -C 6 ) alkylsulfonyl group, wherein B 1 , B 2 , B 3 , B 4 and B 5 are C -R 4 (R 4 is, (d1) a hydrogen atom; (d2) a halogen atom; (d6) (C 1 -C 6) alkoxy group; (d8) halo (C 1 -C 6) alkyl group; or (d10 ) (C 1 -C 6 ) represents an alkylthio group.), B 6 is a nitrogen atom, A
  • R 2 is (b9) a halo (C 1 -C 6 ) alkyl group; (b10) a halo (C 1 -C 6 ) alkoxy group; (b14) a halo (C 1 -C 6 ) alkylthio group; (b15) a halo (C 1 -C 6 ) alkylsulfinyl group; or (b16) a halo (C 1 -C 6 ) alkylsulfonyl group, wherein B 1 , B 2 , B 3 , B 4 and B 5 are C -R 4 (R 4 is (d1) a hydrogen atom; or (d2) a halogen atom), B 6 is a nitrogen atom, A 1 is an oxygen atom, A 2 and A 3 Is CH.
  • the quinoline compound or N-oxide to which the fused heterocyclic ring of the present invention is bonded can be produced, for example, by the following production method, but the present invention is not limited thereto.
  • the quinoline compound or N-oxide to which the condensed heterocyclic ring represented by the general formula (1-1) of the present invention is bonded can be produced by the following steps [a] to [c].
  • Step [a] A step of producing a compound represented by the general formula (2-a) from the compound represented by the general formula (2) and the compound represented by the general formula (3).
  • Step [b] A step of producing a compound represented by the general formula (1-2) from a compound represented by the general formula (2-a) by an intramolecular cyclization reaction.
  • Step [c] A step of producing a quinoline compound or N-oxide to which a condensed heterocyclic ring represented by the general formula (1-1) is bonded by an oxidation reaction from the compound represented by the general formula (1-2).
  • Step [a] The compound represented by the general formula (2-a) is obtained by combining a compound represented by the general formula (2) and a compound represented by the general formula (3) with a base and an inert solvent. It can be produced by reacting in the presence.
  • Examples of the base that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, potassium hydride and the like.
  • Alkali metal hydrides, alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide, and the like, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene and the like
  • Nitrogen-containing aromatic compounds such as quaternary amines, pyridine, dimethylaminopyridine and the like can be mentioned, and the amount used is usually in the range of 1 mol to 10 mol with respect to the compound represented by the general formula (2). Used in.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Hydrocarbons halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethyl
  • the inert solvent include amides such as acetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, Use alone or in combination of two or more Door can be.
  • the amount used may be appropriately selected from the range of 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (2).
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature can be carried out from room temperature to the boiling point of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be usually in the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • step [b] The quinoline compound to which the condensed heterocyclic ring represented by the general formula (1-2) is bonded is obtained by reacting the compound represented by the general formula (2-a) in the presence of an acid and an inert solvent. , Can be produced by reacting.
  • Examples of the acid used in this reaction include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid and benzoic acid, sulfones such as methanesulfonic acid and trifluoromethanesulfonic acid. Acids, phosphoric acids, etc. can be exemplified, and the amount used can be appropriately selected from the range of 0.01-fold mol to 10-fold mol with respect to the compound represented by the general formula (2-a). good.
  • inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid
  • organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid and benzoic acid
  • sulfones such as methanesulfonic acid and trifluoromethanesulfonic acid.
  • Acids, phosphoric acids, etc. can be exemplified,
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Hydrocarbons halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran (THF), esters such as ethyl acetate, dimethyl
  • inert solvents such as amides such as formamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone.
  • Active solvents may be used alone or in combination of two or more. It can be used. Usually, the amount used may be appropriately selected from the range of 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (2-a).
  • the reaction temperature in this reaction can be carried out usually from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it can be usually in the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • step [c] The quinoline compound or N-oxide to which the condensed heterocyclic ring represented by the general formula (1-1) is bonded is obtained by reacting the compound represented by the general formula (1-2) in an inert solvent. It can be produced by reacting with an oxidizing agent.
  • oxidizing agent used in this reaction examples include peroxides such as hydrogen peroxide, perbenzoic acid, and m-chloroperbenzoic acid. These oxidizing agents can be appropriately selected in the range of usually 1 to 5 moles relative to the compound represented by the general formula (1-2).
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction, and examples thereof include chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane, and aromatic carbonization such as benzene, toluene, and xylene.
  • chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane
  • aromatic carbonization such as benzene, toluene, and xylene.
  • Hydrogens, halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, formic acid, acetic acid, etc.
  • Organic solvents N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone, water and the like, and these inert solvents can be used alone or Two or more kinds can be mixed and used. Usually, the amount used thereof may be appropriately selected from the range of usually 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (1-2).
  • the reaction temperature in this reaction may be appropriately selected from the range of usually from ⁇ 10 ° C. to the reflux temperature of the inert solvent used.
  • the reaction time varies depending on the reaction scale, reaction temperature and the like, and is not constant, but may be appropriately selected in the range of usually several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • R 1 , R 2 , A 2 , A 3 , B 1 , B 2 , B 3 , B 4 , B 5 , B 6 , m and n are the same as described above.
  • Step [a ′] A step of producing a compound represented by the general formula (2-a ′) from the compound represented by the general formula (2 ′) and the compound represented by the general formula (3 ′).
  • Step [b ′] A step of producing a compound represented by the general formula (1-2 ′) from the compound represented by the general formula (2-a ′) by an intramolecular cyclization reaction.
  • Step [c] A step of producing a quinoline compound or N-oxide to which a condensed heterocyclic ring represented by the general formula (1-1 ′) is bonded by an oxidation reaction from the compound represented by the general formula (1-2 ′). .
  • Step [a ′] The compound represented by the general formula (2 ′) and the available compound represented by the general formula (3 ′) are reacted in the presence of a condensing agent, a base and an inert solvent. Thus, the compound represented by the general formula (2-a ′) can be produced.
  • Examples of the condensing agent used in this reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDC), diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3- Examples thereof include dicyclohexylcarbodiimide (DCC), chlorocarbonates, 2-chloro-1-methylpyridinium iodide, and the use amount thereof is usually 1 time that of the compound represented by the general formula (2 ′). It may be appropriately selected from the range of mol to 1.5 times mol.
  • the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, acetates such as sodium acetate, potassium acetate, potassium t-butoxide, sodium methoxy And alkali metal alkoxides such as sodium ethoxide, triethylamine, diisopropylethylamine, tertiary amines such as 1,8-diazabicyclo [5.4.0] undec-7-ene, pyridine, dimethylaminopyridine and the like. Nitrogen aromatic compounds and the like can be mentioned, and the amount used is usually in the range of 1 to 10 moles compared to the compound represented by the general formula (2 ′).
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, methylene chloride, chloroform, carbon tetrachloride, etc.
  • Halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, Examples thereof include amides such as dimethylacetamide, ketones such as acetone and methyl ethyl ketone, inert solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone, and these inert solvents can be used alone or Can be used as a mixture of two or more .
  • the amount used may be appropriately selected from the range of usually 0.1 to 100 L per 1 mol of the compound represented by the general formula (2 ').
  • each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
  • the reaction temperature in this reaction can be carried out from room temperature to the boiling point range of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it can be usually in the range of several minutes to 48 hours. After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Step [b ′] The compound represented by the general formula (1-2 ′) is synthesized from the compound represented by the general formula (2-a ′) in the presence of an inert solvent, Synthesis 1981, 1-28. (Preferably using azodicarboxylic acid diesters and triphenylphosphine).
  • step [c] The quinoline compound or N-oxide to which the condensed heterocyclic ring represented by the general formula (1-1 ′) is bonded is produced from the compound represented by the general formula (1-2 ′). It can be produced by the same method as in step 1 [c].
  • R 1 , R 2 , A 2 , A 3 , B 1 , B 2 , B 3 , B 4 , B 5 , and n are the same as described above, and X represents a halogen atom.
  • the quinoline compound to which the condensed heterocyclic ring represented by the general formula (1-2 ′) of the present invention is bonded can also be produced by the following steps [d] to [e].
  • Step [d] A compound represented by general formula (1-2′-2) by reacting a compound represented by general formula (2-2) with a compound represented by general formula (4) Manufacturing process.
  • Step [e] From the compound represented by the general formula (1-2′-2) and the compound represented by the general formula (5), the compound represented by the general formula (1-2 ′) is obtained by a cross-coupling reaction.
  • step [d] For the compound represented by the general formula (1-2′-2), the compound represented by the general formula (2-2) and the compound represented by the general formula (4) are described in the literature. (Org. Lett. 2015, 17, 1445-1448).
  • the quinoline compound to which the condensed heterocyclic ring represented by the general formula (1-2 ′) is bonded includes the compound represented by the general formula (1-2′-2) and the general formula (5) )
  • the compound represented by the general formula (1-2′-2) and the general formula (5) In accordance with the method described in International Publication No. 2013/018928, by carrying out a cross-coupling reaction in the presence of an inert solvent, in the presence of a base and a catalyst. it can.
  • Catalysts preferably used include palladium (0) / carbon, palladium (II) acetate, palladium (II) chloride, bis (triphenylphosphine) palladium (II) chloride, tris (dibenzylideneacetone) dipalladium (0), tetrakis (Triphenylphosphine) palladium (0) and the like can be mentioned, and the amount used thereof is usually 0.0001 to 1 times mol of the compound represented by the general formula (1-2′-2). What is necessary is just to select suitably from the range.
  • This reaction can also be performed by adding a ligand.
  • the ligand include triphenylphosphine (PPh 3 ), methyldiphenylphosphine (Ph 2 PCH 3 ), trifurylphosphine (P (2-furyl) 3 ), tri (o-tolyl) phosphine (P (O-tol) 3 ), tri (cyclohexyl) phosphine (PCy 3 ), dicyclohexylphenylphosphine (PhPCy 2 ), tri (t-butyl) phosphine (Pt-Bu 3 ), 2,2′-bis (diphenylphosphino) -1, 1'-binaphthyl (BINAP), diphenylphosphinoferrocene (DPPF), 1,1'-bis (di-t-butylphosphino) ferrocene (Dt-BPF), N, N-dimethyl-1- [2- ( Diphen
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate, acetates such as sodium acetate and potassium acetate, potassium t Alkali metal alkoxides such as butoxide, sodium methoxide, sodium ethoxide, tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, pyridine, dimethyl
  • examples thereof include nitrogen-containing aromatic compounds such as aminopyridine, and the amount used is usually in the range of 1 to 10 moles compared to the compound represented by the general formula (1-2′-2). used.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Hydrocarbons halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain ethers such as diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran and 2-methyltetrahydrofuran (2-MeTHF), acetic acid
  • inert solvents such as esters such as ethyl, amides such as dimethylformamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone Can these
  • An inert solvent can be used individually or in mixture of 2 or more types. The amount used may be appropriately selected from the range of usually 0.1 to 100 L with respect to 1 mole of the compound represented by the general formula (1-2'-2).
  • the compound represented by the general formula (1-2′-2) and the compound represented by the general formula (5) may be used in equimolar amounts. It is also possible to use excess reactants.
  • the reaction temperature in this reaction can be carried out usually from 0 ° C. in the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it can be usually in the range of several minutes to 48 hours. .
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • R 1 , B 1 , B 2 , B 3 , B 4 , B 5 , and B 6 are as defined above, R represents a (C 1 -C 3 ) alkyl group, and X represents a halogen Indicates an atom.
  • the intermediate represented by the general formula (2) or (2 ′) can be produced by the following steps [f] to [h].
  • Step [f] A step of producing a compound represented by the general formula (2-1) by performing a Sandmeyer reaction on the compound represented by the general formula (2-2).
  • Step [g] From the compound represented by the general formula (2-1) and the compound represented by the general formula (5), in the same manner as in the step [e] of the production method 3, the general formula (2) The process of manufacturing the intermediate body represented by this.
  • Step [h] A step of producing an intermediate represented by the general formula (2 ′) by hydrolyzing the compound represented by the general formula (2).
  • the compound represented by the general formula (2-1) is, for example, an available aminonaphthalene carboxylic acid ester, or a general produced by a method described in the literature (Tetrahedron, 60, 2004, 2937-2942).
  • the compound represented by the formula (2-2) can be produced by reacting according to the method described in Sandmeyer reaction, that is, Chem. Rev. 1988, 88, 765. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and can be purified by recrystallization, column chromatography or the like, if necessary.
  • step [g] The intermediate represented by the general formula (2) is composed of a halocarboxylic acid ester compound represented by the general formula (2-1) and a compound represented by the general formula (5). It can be produced by the same method as in step [e] of production method 3.
  • the intermediate represented by the general formula (2 ′) can be produced by hydrolyzing the intermediate represented by the general formula (2) using a conventional method used in organic synthesis.
  • the intermediate represented by the general formula (3) can be produced by the following steps [i] to [l].
  • Step [i] A compound represented by the general formula (3-3) is produced from the compound represented by the general formula (3-4) and the compound represented by the general formula (6) by a cross-coupling reaction.
  • Step [j] A compound represented by the general formula (3-2) is produced by reacting the compound represented by the general formula (3-3) with the compound represented by the general formula (7).
  • Step [k] A step of producing a compound represented by the general formula (3-1) by introducing a halogen atom onto the ring of the compound represented by the general formula (3-2).
  • Step [l] A step of producing an intermediate represented by the general formula (3) by converting a halogen atom of the compound represented by the general formula (3-1) into an amine.
  • step [i] From the compound represented by the general formula (3-4) produced by the method described in the literature (Tetrahedron 1999, 55, 15067) and the compound represented by the general formula (6), a metal In the presence of a catalyst, a base, and an inert solvent, a cross-coupling reaction is performed according to a method described in the literature (Journal of Synthetic Organic Chemistry, Vol. 69 No. 7 2011; Chem. Rev. 2011, 4475; WO 2013/018928 pamphlet). Thus, the compound represented by the general formula (3-3) can be produced.
  • catalysts such as zero-valent or divalent palladium metals and salts (including complexes) can be used, and they may be supported on activated carbon or the like.
  • Preferable catalysts include palladium (0) / carbon, palladium (II) acetate, palladium (II) chloride, bis (triphenylphosphine) palladium (II) chloride, tetrakis (triphenylphosphine) palladium (0), and the like.
  • the amount used can be appropriately selected from the range of usually 0.0001-fold mole to 1-fold mole relative to the compound represented by the general formula (3-4).
  • This reaction can also be performed by adding a ligand.
  • the ligand include triphenylphosphine (PPh 3 ), methyldiphenylphosphine (Ph 2 PCH 3 ), trifurylphosphine (P (2-furyl) 3 ), tri (o-tolyl) phosphine (P (o-tol) 3 ), tri (cyclohexyl) phosphine (PCy 3 ), dicyclohexylphenylphosphine (PhPCy 2 ), tri (t-butyl) phosphine (P t Bu 3 ), 2,2′-bis (diphenylphosphino) -1, 1′-binaphthyl (BINAP), diphenylphosphinoferrocene (DPPF), 1,1′-bis (di-tert-butylphosphino) ferrocene (D t BPF), N, N-dimethyl-1- [2- ( Di
  • Examples of the base that can be used in the present invention include hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, cesium carbonate, and the like.
  • Examples thereof include organic bases such as picoline, lutidine, triethylamine, tributylamine and diisopropylethylamine.
  • the amount of the base used may be appropriately selected from the range of usually 1-fold mol to 5.0-fold mol based on the compound represented by the general formula (3-4).
  • the reaction temperature in this reaction may usually be in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but is usually selected appropriately within the range of several minutes to 48 hours. It ’s fine.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Step [j] The compound represented by the general formula (3-2) is obtained by reacting the compound represented by the general formula (3-3) with the compound represented by the general formula (7). Can be manufactured.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogens such as methylene chloride, chloroform and carbon tetrachloride.
  • Hydrocarbons halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethyl
  • the inert solvent include amides such as acetamide, ketones such as acetone and methyl ethyl ketone, dimethyl sulfoxide, and 1,3-dimethyl-2-imidazolidinone.
  • the amount used may be appropriately selected from the range of usually 0.1 to 100 L with respect to 1 mol of the compound represented by formula (3-3).
  • a base may be used as necessary.
  • the base include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and other inorganic bases, sodium acetate, potassium acetate.
  • Acetates such as potassium t-butoxide, sodium methoxide, sodium ethoxide, and other alkali metal alkoxides, triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, etc.
  • Nitrogen-containing aromatic compounds such as quaternary amines, pyridine, dimethylaminopyridine and the like can be mentioned, and the amount used is usually 1 to 10 times the molar amount of the compound represented by the general formula (3-3). Used in the molar range.
  • the reaction temperature in this reaction may be appropriately selected within the range of ⁇ 10 ° C. to the reflux temperature of the inert solvent used.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant but may be appropriately selected within the range of several minutes to 48 hours.
  • the compound represented by the general formula (7) can be appropriately selected in the range of 1 to 5 moles compared to the compound represented by the general formula (3-3).
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • the compound represented by the general formula (3-1) can be produced by halogenating the compound represented by the general formula (3-2) with a halogenating agent.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction.
  • examples thereof include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol, and chains such as diethyl ether, tetrahydrofuran, and dioxane.
  • cyclic ethers aromatic hydrocarbons such as benzene, toluene and xylene, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolide
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolide
  • Nonpolar, water, acetic acid and other polar solvents can be mentioned, and these inert solvents can be used alone or in admixture of two or more.
  • the amount used may be appropriately selected from the range of usually 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (3-2).
  • halogenating agent used in the reaction examples include chlorine, bromine and iodine halogen molecules, halogenated succinimides such as NCS and NBS, halogenated hydantoins such as DIH, and thionyl chloride.
  • the reaction temperature in this reaction may be appropriately selected within the range of the reflux temperature of the inert solvent usually used from -30 ° C.
  • the reaction time varies depending on the reaction scale, reaction temperature and the like, and is not constant, but may be appropriately selected in the range of usually several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • the intermediate represented by the general formula (3) can be produced by reacting the compound represented by the general formula (3-1) with ammonia in the presence of a copper catalyst and a solvent. it can.
  • the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • alcohols such as methanol, ethanol, propanol, butanol and 2-propanol
  • aromatics such as benzene, toluene and xylene are used.
  • Group hydrocarbons halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, chain ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, dimethylformamide, dimethylacetamide, N-methylpyrrolidone ( NMP) amides, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and other inert solvents can be exemplified, and these inert solvents are used alone or in combination of two or more. be able to.
  • chain ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, dimethylformamide, dimethylacetamide, N-methylpyrrolidone ( NMP) amides, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone and other inert solvents
  • the copper catalyst used in this reaction may be copper oxide, copper bromide, copper chloride or the like.
  • the amount of the copper catalyst used can be appropriately selected in the range of usually 1 to 5 moles compared to the halopyridazine compound represented by the general formula (3-1).
  • the amount of the solvent used may be appropriately selected from the range of usually 0.1 to 100 L with respect to 1 mol of the compound represented by the general formula (3-1).
  • the reaction temperature in this reaction may be appropriately selected from the range of usually from ⁇ 10 ° C. to the reflux temperature of the inert solvent used.
  • the reaction time varies depending on the reaction scale, reaction temperature, and the like, and is not constant, but may be appropriately selected in the range of usually several minutes to 48 hours.
  • Ammonia can be appropriately selected within a range of 1 to 5 moles relative to the compound represented by the general formula (3-1).
  • an autoclave can be used.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Me represents a methyl group
  • Et represents an ethyl group
  • c-Pr represents a cyclopropyl group
  • Ac represents an acetyl group
  • the Ph group represents a phenyl group.
  • the physical properties indicate melting point (° C.) or 1 H-NMR.
  • the agricultural and horticultural insecticide containing a quinoline compound, N-oxide or a salt thereof to which a fused heterocyclic ring represented by the general formula (1) of the present invention is bonded as an active ingredient is rice, fruit trees, vegetables, other crops and flowers. It is suitable for pest control such as various forests, horticulture, cereal storage, sanitary pests or nematodes that damage plants.
  • Examples of the pests or nematodes include the following. Lepidoptera (Lepidoptera) pests such as Parasa consocia, Redwood (Anomis mesogona), Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, African exotic empti (Spod) (Hyphantria cunea), Awanoiga (Ostrinia furnacalis), Ayayoto (Pseudaletia separata), iga (Tinea translucens), rush saint moth (Bactra furfurana), Ichinomosei (Parnara guttata), Inaitei inferens), Brachmia triannulella, Monema flavescens, Iraqusinu Waiba (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Males flamingo (
  • Hemiptera pests, for example, Nezara antennata, red beetle (Stenotus rubrovittatus), red beetle (Graphosoma rubrolineatum), red beetle (Trigonotylus coelestialium), Aeschynteles maculatus), red beetle (Creontiades pallidifer), red beetle bug (Dysdercus cingulatus), red beetle (Chrysomphalus ficus), red beetle (Aonidiella aurantii), red crab beetle (Graptops) Scale insects (Icerya purchasi), Japanese beetle (Piezodorus hybneri), Japanese beetle (Lagynotomus elongatus), Japanese white-winged beetle (Thaia subrufa), Japanese black beetle (Scotinophara luridaito
  • Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aobaarie-hane-kakushi (Paederus fuscipes), Ahanamuri (Eucetonia roelofsi), Azuki beetle (Callosobruchus chinensis), Arimodosium (Hypera postica), rice weevil (Echinocnemus squameus), rice beetle (Oulema oryzae), rice weevil (Donacia provosti), rice weevil (Lissorhoptrus oryzophilus), Weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), weevil weevil (Involvulus cupreus), weevil (Aulacophora femoralis), pea weevil (Bruchus pisorum) Epilachna viginti
  • Culex pipiens pallens red flies fly (Pegomya hyoscyami), red spider fly (Liriomyza huidobrensis), house fly (Musca domestica), rice flies Flies Fruit flies (Rhacochlaena japonica), fruit flies (Muscina stabulans), fruit flies such as fruit flies (Megaselia spiracularis), giant butterflies (Clogmia albipunctata), mushroom moth (Tipula aino), hormone moth (Pipula) rhynchus), Anopheles sinensis, Japanese flies (Hylemya brassicae), Soybean fly (Asphondylia sp.), Panax fly (Delia platura), Onion fly (Delia antiqua) RRen ), Ceratitis capitata, Bradysia agrestis, sugar beetle fly (P
  • Hymenoptera Pristomyrmex ponnes
  • Arbatidae Monomelium pharaonis
  • Pheidole noda Athalia rosae
  • Cristoforma Kuriphilus
  • Hornets black bee (Athalia infumata infumata), horned bee (Arge g pagana), Japanese bee (Athalia ⁇ japonica), cricket (Acromyrmex spp.), Fire ant (Solenopsis spp.), Apple honey bee (Arlen ali) (Ochetellus glaber) and the like.
  • insects of the order Diptera Hortocoryphus lineosus
  • Kera Gryllotalpa sp.
  • Coago Oxya hyla intricata
  • Cobainago Oxya yezoensis
  • Tosama locust Locusta migrago
  • Oneya Homorocoryphus jezoensis
  • emma cricket Teogryllus emma
  • Thrips examples of thrips of the order Thrips (Selenothrips rubrocinctus), thrips (Stenchaetothrips biformis), Thrips thrips (Haplothrips , Lithrips floridensis, Thrips simplex, Thrips nigropilosus, Helothripes Leeuwenia pasanii), Shiritaku Thrips pasaniae, Citrus Srips citri, Hypothrips chinensis, Soybean Thrips (Mycterothrips glycines), Da Thrips setosus, Thripsrtsaw Thrips hawaiiensis, Haplothrips kurdjumovi, Thrips coloratus , Lilyripa vaneeckei, and the like.
  • mite moths (Leptotrombidium akamushi), Ashinowa spider mite (Tetranychus ludeni), American dock ticks (Dermacentor variabilis), Ichinami spider mite (Tetranychus truncatus), house dust mite (Ornithonyssus bacoti), mite Tetranychus viennensis), ticks (Tetranychus kanzawai), ticks (Rhipicephalus sanguineus) and other ticks (Cheyletus acc malaccensis), stag beetle tick (Tyrophagus putrescent moth) Tick (Dermacentor taiwanicus), Chinese cabbage mite (Acaphylla theavagrans), Chinese dust mite (Polyphagotarsonemus latus), Tomato mite (Aculops lycopersici), Trichoid mite (Ornithonyssus sylvairum), Nami spider mite (
  • Amite termites (Reticulitermes miyatakei), American termites (Incisitermes minor), Termites (Coptotermes formosanus), Termites (Hodotermopsis japonica), Common termites (Reticulitermes termm ants) , Glyptotermes , Nakajima termite (Glyptotermes nakajimai), Nitobe termite (Pericapritermes nitobei), Yamato termite (Reticulitermes speratus) and the like.
  • cockroach Periplaneta fuliginosa
  • German cockroach Blattella germanica
  • Great cockroach Blatta orientalis
  • Greater cockroach Periplaneta brunnea
  • Greater cockroach Blattella lituriplanet (Periplaneta americana) and the like.
  • fleas examples include human fleas (Pulex irritans), cat fleas (Ctenocephalides felis), and fleas (Ceratophyllus gallinae).
  • Nematodes for example, strawberry nematode (Nothotylenchus acris), rice scallop nematode (Aphelenchoides besseyi), red-footed nematode (Pratylenchus penetrans), red-knot nematode (Meloidogyne hapla), sweet potato nematode (Meloidogyne rostochiensis), Javaloid nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern nematode nematode (Pratylenchus coffeae), and pterolenchus nematode (Pratylenchus neglectus)
  • mollusks examples include Pomacea canaliculata, Achatina fulica, slug (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Acusta despecta Is mentioned.
  • the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against tomato kibaga (Tuta absoluta) as other pests.
  • animal parasite ticks Boophilus microplus
  • black tick ticks Raicephalus sanguineus
  • yellow tick ticks Haemaphysalis longicornis
  • yellow ticks Haemaphysalis flava
  • tsurigane tick ticks Haemaphysata tick
  • Tick Haemaphysalis concinna
  • tick Haemaphysalis japonica
  • tuna Haemaphysalis kitaokai
  • tick Haemaphysalis ias
  • tick Ixodes ovatus
  • tick desmite Ticks Dermanyssus, ticks such as Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis gallinae
  • avian mite Ornithonyssus sylviarum
  • fleas to be controlled include, for example, ectoparasite worms belonging to the order Flea (Siphonaptera), more specifically fleas belonging to the family Flea (Pulicidae), Cleaphyllus (Ceratephyllus), etc. .
  • Fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), elephant fleas (Echidnophaga gallinacea), keops mouse fleas (Xenopsylla cheopis), Leptopsylla segnis), European rat minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).
  • ectoparasites to be controlled include, for example, bovine lice (Haematopinus eurysternus), foal lice (Haematopinus asini), sheep lice (Dalmalinia ovis), bovine lice (Linognathus vituli), pig lice (Haematopinus suis), hirke us lice And lice like head lice (Pediculus capitis), and lice like dog lice (Trichodectes canis); Examples include pests.
  • endoparasites include nematodes such as pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, manson cleft worms, broad-headed crest worms, berries Tapeworms such as tapeworms, multi-headed tapeworms, single-banded tapeworms, and multi-banded tapeworms, flukes such as Schistosoma japonicum, and liver fluke, and coccidium, malaria parasites, intestinal granulocysts, toxoplasma And protozoa such as Cryptosporidium.
  • the administration of the quinoline compound, N-oxide or a salt thereof to which the condensed heterocyclic ring represented by the general formula (1) of the present invention is bonded may be in vivo or in vitro.
  • Agricultural and horticultural insecticides containing quinoline compounds, N-oxides or salts thereof to which a fused heterocycle represented by the general formula (1) of the present invention is bound as active ingredients are paddy field crops, field crops, fruit trees, vegetables, etc. Since it has a remarkable control effect against the above-mentioned pests that damage crops and florets, seedling facilities, paddy fields before the occurrence of the pests or when the occurrence of the pests is confirmed, according to the time when the occurrence of the pests is predicted , Fields, fruit trees, vegetables, other crops, seeds such as flower buds, paddy water, foliage or soil, etc., and the desired effect of the agricultural and horticultural insecticide of the present invention can be achieved. It is.
  • Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited, and examples thereof include cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans (soybean, Red beans, broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, peaches, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomatoes, spinach, broccoli, lettuce, onions, green onions (satsuki, parsley), peppers, eggplants, strawberries, peppers, ladle, leek, etc.
  • cereals eg, rice, barley, wheat, rye, oats, corn, etc.
  • beans soybean, Red beans, broad beans, green beans, green beans, peanuts, etc.
  • fruit trees and fruits apples, citrus fruits, pears, peaches, pe
  • the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors such as glyphosate
  • glutamine synthase inhibitors such as glufosinate, cetoxydim and the like.
  • plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as
  • Plants to which tolerance to an acetyl-CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990).
  • a mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005).
  • Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation into the plant or introducing a mutation associated with imparting resistance into the plant acetyl-CoA carboxylase, and further, chimeric plastic technology (Gura T. et al. 1999.
  • toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus or Bacillus popirie; ⁇ - such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc.
  • ⁇ - such as Cry1Ab, Cry1Ac, Cry1F,
  • Bosome 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 plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, Cry35Ab and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A etc.
  • insecticidal protein hybrid toxins partially defective toxins, and modified toxins.
  • 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.
  • Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes.
  • the agricultural and horticultural insecticides of the present invention can be used in combination or systematized with these techniques.
  • the insecticide for agricultural and horticultural use according to the present invention is used as it is to control various pests, or appropriately diluted with water or the like, or suspended in an amount effective for controlling the pests or nematodes.
  • pests and nematodes that occur in fruit trees, cereals, vegetables, etc.
  • seed immersion in seeds, seed dressing, calper treatment Etc seed treatment, soil all layer mixing, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc. It can also be absorbed and used.
  • it can be used for nutrient solution in nutrient solution (hydroponics) cultivation, smoke, or trunk injection.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, appropriately diluted with water or the like or suspended in an amount effective for pest control in a place where the occurrence of the pest is predicted.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, appropriately diluted with water or the like or suspended in an amount effective for pest control in a place where the occurrence of the pest is predicted.
  • they can also be used as application to house building materials, smoke, bait and the like.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at the initial stage of cultivation used for the propagation of plants, for example, for seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings. Mention may be made of plants for vegetative propagation.
  • the “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, high It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.
  • a spraying method for crop foliage stored grain pests, house pests, hygiene pests, forest pests, etc., dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water as appropriate.
  • Examples of the application method to the soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc.
  • a method of spraying to a nursery, etc. a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body
  • Examples thereof include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
  • the dosage form may vary depending on the time of application such as application during sowing, greening period, application during transplantation, etc., but agents such as powder, granule wettable powder, granules, etc. Apply by mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and the various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate formulation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
  • the plant source of the plant being cultivated In field crops, it can be treated to seeds or a cultivation carrier close to the plant body from sowing to raising seedling.
  • treatment on the plant source of the plant being cultivated is suitable.
  • a spray treatment using a granule or a irrigation treatment in a liquid of a drug diluted or not diluted with water can be performed. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
  • the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferred.
  • a granule is treated in a planting hole at the time of planting or is mixed with a cultivation carrier in the vicinity of the transplantation site.
  • the agricultural and horticultural insecticide of the present invention is generally used in a form convenient for use according to a conventional method for agricultural chemical preparations. That is, the quinoline compound, N-oxide or salt thereof to which the condensed heterocyclic ring represented by the general formula (1) of the present invention is bonded is suitable for use as a suitable inert carrier or, if necessary, with an auxiliary agent.
  • the composition of the present invention can contain, in addition to the active ingredient, additive components usually used in agricultural chemical formulations or animal parasite control agents as required.
  • additive components include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed. These additive components may be used alone or in combination of two or more.
  • the solid support examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Alcohols such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • Ethers normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons
  • Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.
  • Esters lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
  • surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxye Lenalkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene dio
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
  • Polyethylene glycol polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (eg, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinyl pyrrolidone, maleic acid and styrene Polymers, (meth) acrylic acid copolymers, half-esters of polyhydric alcohol polymers and dicarboxylic acid anhydrides, polystyrene sulfonic acid water-soluble salts, Emissions, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
  • phospholipid eg, cephalin, lecithin, etc.
  • cellulose powder dextrin
  • polyaminocarboxylic acid chelate compound cross-linked polyviny
  • thickener examples include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica and white carbon.
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.
  • antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinylpyrrolidone, fumed silica (fumed silica), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.
  • the decomposition inhibitor examples include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • desiccants such as zeolite, quicklime and magnesium oxide
  • antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds
  • ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
  • functional aids such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention.
  • 0.01 to 50 parts by weight 0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide
  • the amount of the agricultural and horticultural insecticide of the present invention depends on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc. Although it varies, the active ingredient compound may be suitably selected from the range of 0.001 g to 10 kg per 10 ares, preferably 0.01 g to 1 kg depending on the purpose.
  • Agricultural and horticultural insecticides of the present invention are pests to be controlled, other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, for the purpose of expanding the appropriate period of control or reducing the dose. It can also be used by mixing with biological pesticides, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the usage situation.
  • Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, acibenzolar-S-methyl. ), Azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isothianyl (Isotianil), isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, eclomeole, echlomez Edifenphos, etaconazole, ethaboxam, e
  • herbicides for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, aslam, acetochlor, Atrazine, atraton, anisuron, anilofos, abiglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino Cyclopyrachlor (aminocyclopyrachlor), aminopyralid (aminopyralid), Amibu Gin (amibuzin), amiprophos-methyl,
  • biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopoxivirus, EPV) ) Virus preparations, Monocrosporium ⁇ ⁇ phymatophagum, Steinernema ⁇ carpocapsae, Steinernema kushidai, Pasturia ⁇ pene insecticides, and Pasturia pene insecticides Sterilization of microbial pesticides, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc.
  • microbial pesticide to be used by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.
  • examples of biological pesticides include Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusahysrica persimilis), natural enemies such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) ) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, 14-methyl-1 - May also be used in combination with pheromone agents such as octadecene It is a function.
  • pheromone agents such as octadecene It is a function.
  • the target product (10 mg) was obtained by silica gel column chromatography. Physical properties: 1 H-NMR (400 MHz, CDCl 3 ) ⁇ 9.11 (s, 1H), 8.29 (d, 1H), 8.23 (s, 1H), 8.17 (d, 1H), 8 .07 (t, 1H), 7.90 (t, 1H), 4.13 (s, 3H), 3.85 (q, 2H), 1.40 (t, 3H)
  • Formulation Example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Equal weight mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above is uniformly mixed and dissolved to prepare an emulsion.
  • Formulation Example 2 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.
  • Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
  • Formulation Example 4 Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above mixture is uniformly mixed and ground to obtain a wettable powder.
  • Test Example 1 Control value test against peach aphid (Myzus persicae) Chinese cabbage was planted in a plastic pot having a diameter of 8 cm and a height of 8 cm to breed a peach aphid, and the number of parasites in each pot was investigated.
  • the quinoline compound, N-oxide or a salt thereof to which the condensed heterocyclic ring represented by the general formula (1) of the present invention is bonded is dispersed in water and diluted to a chemical solution of 500 ppm, and the chemical solution is sprayed on the stems and leaves of potted Chinese cabbage.
  • Ta Number of parasites before spraying in the treated area
  • Ca Number of parasites before spraying in the untreated area
  • C Number of parasites after spraying in the untreated area
  • the compounds of the present invention 1-1, 1-3, 1-10, 1-11, 1-24, 1-29, 1-30, 1-32, 1-33, 1-36, 1-37 , 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 2-1, 2 -3, 3-1, 3-3, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-17, 3-27, 3-37, 3-38 , 3-39, 3-40, 3-41, 3-42, 4-1, 4-2, 3-3, 4-4, 4-5, 4-6, 4-7, 4-8, 4 -9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21 4-22, 4-23, 4-24, 4-25, 5-1 and 6-1 are A Showed activity.
  • Test Example 2 Insecticidal test for Laodelphax striatella
  • a quinoline compound, N-oxide or a salt thereof to which a condensed heterocyclic ring represented by the general formula (1) of the present invention is bonded is dispersed in water and diluted to a chemical solution of 500 ppm.
  • Rice seedlings (variety: Nipponbare) were soaked for 30 seconds, air-dried, placed in a glass test tube, inoculated with 10 each of the three Japanese beetles, and then plugged, and the number of live and dead insects was investigated 8 days after inoculation.
  • the corrected death rate was calculated from the following formula, and the determination was made according to the following criteria.
  • the compounds of the present invention 1-1, 1-3, 1-10, 1-11, 1-24, 1-29, 1-30, 1-32, 1-33, 1-36, 1-37 , 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 2-1, 2 -3, 3-1, 3-3, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-17, 3-27, 3-37, 3-38 , 3-39, 3-40, 3-41, 3-42, 4-1, 4-2, 3-3, 4-4, 4-5, 4-6, 4-7, 4-8, 4 -9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21 4-22, 4-23, 4-24, 4-25, 5-1 and 6-1 are A Showed activity.
  • Test Example 3 Insecticidal test for Plutella xylostella Sponge seedlings are allowed to lay eggs and lay eggs, and two days after release, Chinese cabbage seedlings with spawning eggs are condensed into a complex of the general formula (1) of the present invention.
  • a drug containing a ring-bound quinoline compound, N-oxide or a salt thereof as an active ingredient was immersed in a chemical solution diluted to 500 ppm with water for about 30 seconds, air-dried, and then allowed to stand in a thermostatic chamber at 25 ° C.
  • Six days after immersion in the chemical solution the number of hatching insects was investigated, the death rate was calculated by the following formula, and the determination was made according to the criteria of Test Example 2. 1 ward, 10 heads, 3 systems.
  • the compounds of the present invention 1-1, 1-3, 1-10, 1-11, 1-24, 1-29, 1-30, 1-32, 1-33, 1-36, 1-37 , 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 2-1, 2 -3, 3-1, 3-3, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-17, 3-27, 3-37, 3-38 , 3-39, 3-40, 3-41, 3-42, 4-1, 4-2, 3-3, 4-4, 4-5, 4-6, 4-7, 4-8, 4 -9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21 4-22, 4-23, 4-24, 4-25, 5-1 and 6-1 are A Showed activity.
  • the compounds according to the present invention have an excellent control effect against a wide range of agricultural and horticultural pests and are useful.

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  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Le problème à la base de la présente invention concerne la mise au point et l'utilisation d'un nouvel insecticide agricole et horticole, en raison de facteurs tels que la dévastation existante au niveau de la production de cultures dans l'agriculture, l'horticulture, etc. provoquée par des insectes nuisibles, etc., l'apparition d'insectes nuisibles qui sont résistants aux produits pharmaceutiques existants, etc. La présente invention concerne : un composé de quinoléine présentant un hétérocycle condensé lié à celui-ci, qui est représenté par la formule générale (1) {dans la formule : R1 représente un groupe éthyle ; R2 représente un groupe halogénoalkyle ou un groupe halogénoalkylthio ; A1 représente un groupe N-méthyle ou un atome d'oxygène ; A2 et A3 représentent chacun un atome d'azote ou CH ; B1, B2, B3, B4 et B5 représentent chacun un groupe CH ; et B6 représente un atome d'azote ; m représente 2 ; et n représente 1} ; un N-oxyde ou des sels correspondants ; un insecticide agricole et horticole contenant, comme principe actif, le composé de quinoléine ou le N-oxyde ou un sel correspondant ; et un procédé d'utilisation de l'insecticide agricole et horticole.
PCT/JP2017/007161 2016-02-26 2017-02-24 Composé de quinoléine présentant un hétérocycle condensé lié à celui-ci, n-oxyde ou sels correspondants et insecticide agricole et horticole contenant le composé et procédé pour son utilisation Ceased WO2017146220A1 (fr)

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WO2018084142A1 (fr) * 2016-11-01 2018-05-11 日本農薬株式会社 Composé de quinoléine ayant un groupe oxime, n-oxyde ou sel de celui-ci, insecticide agricole et horticole le comprenant et son procédé d'utilisation
WO2019008072A1 (fr) 2017-07-05 2019-01-10 Syngenta Participations Ag Dérivés hétérocycliques à activité pesticide comportant des substituants contenant du soufre
WO2019009387A1 (fr) * 2017-07-07 2019-01-10 日本農薬株式会社 Procédé de production d'un composé heterocyclique condensé
US10544163B2 (en) 2016-03-10 2020-01-28 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
WO2020173861A1 (fr) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
US10947253B2 (en) 2019-08-05 2021-03-16 Ankh Life Sciences Limited Fused polycyclic dimers
CN113710669A (zh) * 2019-02-26 2021-11-26 拜耳公司 作为农药的稠合双环杂环衍生物
WO2024189139A1 (fr) 2023-03-14 2024-09-19 Syngenta Crop Protection Ag Lutte contre des nuisibles résistants aux insecticides
US12129265B2 (en) 2020-07-21 2024-10-29 Ankh Life Sciences Limited Therapeutic agents and uses thereof

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US10544163B2 (en) 2016-03-10 2020-01-28 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10640518B2 (en) 2016-03-10 2020-05-05 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
US10759815B2 (en) 2016-03-10 2020-09-01 Nissan Chemical Corporation Condensed heterocyclic compounds and pesticides
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JPWO2018070503A1 (ja) * 2016-10-13 2019-07-25 日本農薬株式会社 １ｈ‐ピロロピリジン化合物、若しくはそのｎ‐オキシド、又はその塩類及び該化合物を含有する農園芸用殺虫剤並びにその使用方法
WO2018070503A1 (fr) * 2016-10-13 2018-04-19 日本農薬株式会社 Composé 1h-pyrrolopyridine ou n-oxyde ou sel de celui-ci, insecticide agricole et horticole contenant ledit composé, et procédé d'utilisation dudit insecticide
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AU2017354298B2 (en) * 2016-11-01 2020-11-12 Nihon Nohyaku Co., Ltd. Oxime group-containing quinoline compound, N-oxide thereof or salt thereof, agricultural and horticultural insecticide comprising the compound, and method for using the insecticide
WO2019008072A1 (fr) 2017-07-05 2019-01-10 Syngenta Participations Ag Dérivés hétérocycliques à activité pesticide comportant des substituants contenant du soufre
WO2019009387A1 (fr) * 2017-07-07 2019-01-10 日本農薬株式会社 Procédé de production d'un composé heterocyclique condensé
WO2020173861A1 (fr) 2019-02-26 2020-09-03 Bayer Aktiengesellschaft Dérivés hétérocycliques bicycliques condensés utilisés comme pesticides
CN113710669A (zh) * 2019-02-26 2021-11-26 拜耳公司 作为农药的稠合双环杂环衍生物
JP2022521438A (ja) * 2019-02-26 2022-04-07 バイエル・アクチエンゲゼルシヤフト 有害生物防除剤としての縮合二環式複素環式誘導体
JP2022521439A (ja) * 2019-02-26 2022-04-07 バイエル・アクチエンゲゼルシヤフト 有害生物防除剤としての縮合二環式複素環式誘導体
JP7535532B2 (ja) 2019-02-26 2024-08-16 バイエル・アクチエンゲゼルシヤフト 有害生物防除剤としての縮合二環式複素環式誘導体
JP7664166B2 (ja) 2019-02-26 2025-04-17 バイエル・アクチエンゲゼルシヤフト 有害生物防除剤としての縮合二環式複素環式誘導体
US12297196B2 (en) 2019-02-26 2025-05-13 Bayer Aktiengesellschaft Condensed bicyclic heterocyclic derivatives as pest control agents
US10947253B2 (en) 2019-08-05 2021-03-16 Ankh Life Sciences Limited Fused polycyclic dimers
US12129265B2 (en) 2020-07-21 2024-10-29 Ankh Life Sciences Limited Therapeutic agents and uses thereof
WO2024189139A1 (fr) 2023-03-14 2024-09-19 Syngenta Crop Protection Ag Lutte contre des nuisibles résistants aux insecticides

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