WO2016175017A1 - Nouveau dérivé 4-pyridinecarboxamide et agents agricoles et horticoles le contenant comme principe actif - Google Patents

Nouveau dérivé 4-pyridinecarboxamide et agents agricoles et horticoles le contenant comme principe actif Download PDF

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WO2016175017A1
WO2016175017A1 PCT/JP2016/061708 JP2016061708W WO2016175017A1 WO 2016175017 A1 WO2016175017 A1 WO 2016175017A1 JP 2016061708 W JP2016061708 W JP 2016061708W WO 2016175017 A1 WO2016175017 A1 WO 2016175017A1
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group
compound
haloalkyl
alkyl
formula
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秀一 薄井
一秋 小山
恒一 荒木
麻紀子 牛江
福地　俊樹
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アグロカネショウ株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—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
    • 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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/18—Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a novel 4-pyridinecarboxamide derivative, and an agricultural and horticultural drug containing the derivative as an active ingredient, particularly an agricultural and horticultural insecticide.
  • Patent Document 1 describes that a compound of the following formula is useful as an agricultural and horticultural nematicide.
  • Patent Document 2 discloses a 4-pyridinecarboxamide compound represented by the following formula.
  • Patent Document 3 discloses a 4-pyridinecarboxamide compound represented by the following formula as a pharmaceutical intermediate.
  • Patent Document 4 discloses a 4-pyridinecarboxamide compound represented by the following formula as a pharmaceutical intermediate.
  • Patent Document 5 discloses a 3-pyridinecarboxamide compound of the following formula as an endoparasite control agent, but does not disclose a 4-pyridinecarboxamide compound.
  • Patent Document 6 discloses a 2-pyridinecarboxamide compound of the following formula as an insecticide, but does not disclose a 4-pyridinecarboxamide compound.
  • Non-Patent Document 1 discloses a 4-pyridinecarboxamide compound represented by the following formula as a reaction intermediate.
  • R 1 represents a C 1-6 alkyl group or a C 1-6 haloalkyl group
  • R 2 represents a hydrogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group
  • G 1 , G 2 , G 3 , G 4 and G 5 each independently represent a nitrogen atom or CR 3 (provided that G 1 , G 2 , G 3 , G 4 and G 5 are simultaneously nitrogen atoms
  • at least one of G 1 , G 2 , G 3 , G 4 and G 5 is CR 3
  • R 3 may be the same or different and is a hydrogen atom, a halogen atom, a C 1-12 alkyl group, a C 1-12 haloalkyl group, a C 3-8 cycloalkyl group, a C 1-6 alkoxy group, a C 3-6 Alkenyloxy group, C 3-6 alkynyloxy group, C 1-6 haloalkoxy group, C 3-6 hal
  • R 1 represents a C 1-6 alkyl group, an N-oxide thereof or a salt thereof.
  • R 2 represents a hydrogen atom or a C 1-6 alkyl group.
  • the compounds of the present invention have excellent effects as agricultural and horticultural agents, particularly agricultural and horticultural insecticides. Furthermore, the compounds of the present invention are also effective against pests parasitic on pets such as dogs and cats or livestock such as cows and sheep.
  • R 1 represents a C 1-6 alkyl group or a C 1-6 haloalkyl group
  • R 2 represents a hydrogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group
  • G 1 , G 2 , G 3 , G 4 and G 5 each independently represent a nitrogen atom or CR 3 (provided that G 1 , G 2 , G 3 , G 4 and G 5 are simultaneously nitrogen atoms
  • R 3 may be the same or different and is a hydrogen atom, a halogen atom, a C 1-12 alkyl group, a C 1-12 haloalkyl group, a C 3-8 cycloalkyl group, a C 1-6 alkoxy group, a C 3-6 Alkenyloxy group, C 3-6 al
  • C 1-6 alkyl group of R 1 is, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group.
  • the “C 1-6 haloalkyl group” for R 1 refers to a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different.
  • Examples of the “C 1-6 haloalkyl group” include a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, and a 1-fluoroethyl group.
  • 2-fluoroethyl group 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 1- Fluoroisopropyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, 4-fluorobutyl group, 4-chlorobutyl, nonafluorobutyl group, 5,5,5-trifluoro Pentyl group, 5-chloropentyl group, undecafluoropentyl group, 6,6, A linear or branched chain having 1 to 6 carbon atoms substituted with 1 to 13, preferably 1 to 9, halogen atoms such as 6-trifluorohexyl group, 6-chlorohexyl group and tridecafluorohexyl
  • R 1 is preferably a “C 1-6 alkyl group”, more preferably a “C 1-3 alkyl group”, particularly preferably a methyl group or an ethyl group.
  • the “C 1-6 alkyl group” for R 2 is the same as defined for the “C 1-6 alkyl group” for R 1 .
  • a “C 1-3 alkyl group” is preferable, and a methyl group or an ethyl group is particularly preferable.
  • the “C 1-6 haloalkyl group” for R 2 is the same as that defined for the “C 1-6 haloalkyl group” for R 1 .
  • the “C 1-6 haloalkyl group” for R 2 is preferably a “C 1-3 haloalkyl group”.
  • halogen atom for R 3 refers to a chlorine atom, bromine atom, iodine atom or fluorine atom.
  • the “C 1-12 alkyl group” of R 3 is, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group. Or a linear or branched alkyl group having 1 to 12 carbon atoms.
  • C 1-12 haloalkyl group for R 3 refers to a linear or branched alkyl group having 1 to 12 carbon atoms substituted with one or more halogen atoms which may be the same or different.
  • Examples of the “C 1-6 haloalkyl group” include a trifluoromethyl group and a pentafluoroethyl group.
  • C 3-8 cycloalkyl group refers to a cyclic cycloalkyl group having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
  • the “C 1-6 alkoxy group” for R 3 is, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a cyclopropyloxy group, an n-butoxy group, a sec-butoxy group, or a tert-butoxy group.
  • the “C 3-6 alkenyloxy group” for R 3 is, for example, allyloxy group, isopropenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 1-methyl-2-propenyloxy group, 2-pentenyloxy group.
  • 3-pentenyloxy group 4-pentenyloxy group, 1,1-dimethyl-2-propenyloxy group, 1-ethyl-2-propenyloxy group, 1-methyl-2-butenyloxy group, 1-methyl-3- Butenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1,1-dimethyl-2-butenyloxy group, 1,1-dimethyl-3-butenyloxy group, etc. Or a straight or branched alkenyloxy group having 3 to 6 carbon atoms and having at least one double bond at any position.
  • the “C 3-6 alkynyloxy group” for R 3 is, for example, a 2-propynyloxy group, a 1-methyl-2-propynyloxy group, a 1,1-dimethyl-2-propynyloxy group, a 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1-methyl-2-butynyloxy group, 1-methyl -3-butynyloxy group, 1,1-dimethyl-2-butynyloxy group, 1,1-dimethyl-3-butynyloxy group, 1-methyl-3-pentynyloxy group, 1-methyl-4-pentynyloxy group A linear or branched alkynyloxy group having 3 to 6 carbon atoms and having at least one triple bond at an arbitrary position.
  • the “C 1-6 haloalkoxy group” for R 3 is, for example, fluoromethoxy group, dichloromethoxy group, trichloromethoxy group, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, dichlorofluoro Methoxy group, 1-fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2- Such as trichloroethoxy group, pentafluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group, 1 to 6 carbon atoms linear or substituted with 1 to 9 halogen atoms It includes branched chain alk
  • the “C 3-6 haloalkenyloxy group” for R 3 is, for example, a 3-chloro-2-propenyloxy group, a 3,3-difluoro-2-allyloxy group, a 3,3-dichloro-2-allyloxy group, 4,4,4-trifluoro-2-butenyloxy group, 4,4,4-trifluoro-3-butenyloxy group, 5-chloro-3-pentenyloxy group, 6-fluoro-2-hexenyloxy group, etc.
  • An alkenyloxy group is, for example, a 3-chloro-2-propenyloxy group, a 3,3-difluoro-2-allyloxy group, a 3,3-dichloro-2-allyloxy group, 4,4,4-tri
  • the “C 3-6 haloalkynyloxy group” for R 3 is 4,4,4-trifluoro-2-butynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 1-methyl- 3 carbon atoms having at least one triple bond at an arbitrary position such as 3,3,3-trifluoro-2-butynyloxy group, 1-methyl-5,5,5-trifluoro-2-pentynyloxy group, etc. 6 to 6 linear or branched alkynyloxy groups, which are substituted with 1 to 9, preferably 1 to 6, halogen atoms.
  • the “C 1-6 alkylthio group” for R 3 is, for example, methylthio group, ethylthio group, n-propylthio group, isopropylthio group, cyclopropylthio group, n-butylthio group, sec-butylthio group, tert-butylthio group.
  • the “C 1-6 alkylsulfinyl group” for R 3 is, for example, methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfinyl group, cyclopropylsulfinyl group, n-butylsulfinyl group, sec-butylsulfinyl group.
  • a straight-chain or branched alkylsulfinyl group having 1 to 6 carbon atoms such as a group, tert-butylsulfinyl group, n-pentylsulfinyl group, n-hexylsulfinyl group.
  • the “C 1-6 alkylsulfonyl group” for R 3 is, for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isoprosulfonyl group, cyclopropylsulfonyl group, n-butylsulfonyl group, sec-butylsulfonyl group.
  • a straight-chain or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a group, tert-butylsulfonyl group, n-pentylsulfonyl group, n-hexylsulfonyl group and the like.
  • the “C 1-6 haloalkylthio group” for R 3 is, for example, a difluoromethylthio group, a trifluoromethylthio group, a monochloromethylthio group, a dichloromethylthio group, a trichloromethylthio group, a monobromomethylthio group, a dibromomethylthio group, a tribromomethylthio group.
  • the “C 1-6 haloalkylsulfinyl group” of R 3 is difluoromethylsulfinyl group, trifluoromethylsulfinyl group, dichloromethylsulfinyl group, trichloromethylsulfinyl group, monobromomethylsulfinyl group, dibromomethylsulfinyl group, tribromomethyl Sulfinyl group, 1-fluoroethylsulfinyl group, 2-fluoroethylsulfinyl group, 2,2-difluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2-chloro-2,2-difluoroethylsulfinyl group 1-chloroethylsulfinyl group, 2-chloroethylsulfinyl group, 2,2-dichloroethylsulfiny
  • the “C 1-6 haloalkylsulfonyl group” of R 3 is a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a dichloromethylsulfonyl group, a trichloromethylsulfsulfonyl group, a monobromomethylsulfonyl group, a dibromomethylsulfonyl group, Tribromomethylsulfonyl group, 1-fluoroethylsulfonyl group, 2-fluoroethylsulfonyl group, 2,2-difluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2-chloro-2,2-difluoro Ethylsulfonyl group, 1-chloroethylsulfonyl group, 2-chloroethylsulfonyl group
  • halogen atom for R 4 and R 5 is the same as that defined for the “halogen atom” for R 3 .
  • the “C 1-6 alkyl group” for R 4 and R 5 is the same as defined for the “C 1-6 alkyl group” for R 1 .
  • the “C 1-6 haloalkyl group” for R 4 and R 5 is the same as defined for the “C 1-6 haloalkyl group” for R 1 .
  • the “C 3-8 cycloalkyl group” for R 4 and R 5 is the same as that defined for the “C 3-8 cycloalkyl group” for R 3 .
  • the “C 1-6 alkoxy group” for R 4 and R 5 is the same as that defined for the “C 1-6 alkoxy group” for R 3 .
  • the “C 1-6 haloalkoxy group” for R 4 and R 5 is the same as that defined for the “C 1-6 haloalkoxy group” for R 3 .
  • the “C 1-6 alkylthio group” for R 4 and R 5 is the same as that defined for the “C 1-6 alkylthio group” for R 3 .
  • C 1-6 alkylsulfinyl group” for R 4 and R 5 is the same as that defined for the “C 1-6 alkylsulfinyl group” for R 3 .
  • C 1-4 alkylsulfonyl group for R 4 and R 5 refers to a linear or branched alkylsulfonyl group having 1 to 4 carbon atoms such as a methanesulfonyl group or an ethanesulfonyl group.
  • C 1-6 haloalkylthio group for R 4 and R 5 is the same as that defined for the “C 1-6 haloalkylthio group” for R 3 .
  • C 1-6 haloalkylsulfinyl group for R 4 and R 5 is the same as that defined for the “C 1-6 haloalkylsulfinyl group” for R 3 .
  • C 1-6 haloalkylsulfonyl group for R 4 and R 5 is the same as that defined for the “C 1-6 haloalkylsulfonyl group” for R 3 .
  • R 3 when two R 3 constitute a ring including G 1 to G 5 and are bonded to each of two adjacent carbon atoms, the two R 3 are bonded to each other; Furthermore, a saturated or unsaturated 5- or 6-membered ring may be formed together with the above-mentioned ring carbon atoms.
  • the ring to be formed include a naphthalene ring and a quinoline ring.
  • halogen atom of X is the same as defined for the “halogen atom” of R 3 .
  • C 1-6 alkyl group of X is the same as defined in the "C 1-6 alkyl group” of R 1.
  • C 1-6 haloalkyl group” for X is the same as that defined for the “C 1-6 haloalkyl group” for R 1 .
  • C 3-8 cycloalkyl group" of X is the same as those defined with “C 3-8 cycloalkyl group” of R 3.
  • C 1-6 alkoxy group of X is the same as defined in the "C 1-6 alkoxy group” of R 3.
  • X is preferably a hydrogen atom.
  • N represents an integer of 0-2.
  • M represents an integer of 0 to 3, preferably 0.
  • the compound of the present invention may be an N-oxide of a 4-pyridinecarboxamide derivative represented by the above formula (I) or a salt thereof.
  • the N-oxide of the 4-pyridinecarboxamide derivative represented by the formula (I) may be pyridine N-oxide.
  • Examples of the salt of the 4-pyridinecarboxamide derivative represented by the formula (I) include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, and sulfate.
  • examples thereof include organic acid salts such as acid salts, methanesulfonate, benzenesulfonate, and p-toluenesulfonate.
  • the 4-pyridinecarboxamide derivative represented by the formula (I) exists as two or more optical isomers and diastereomers derived from one or more asymmetric centers contained in the structure.
  • the present invention includes each optical isomer.
  • the present invention also includes a mixture containing the above-mentioned optical isomers in an arbitrary ratio.
  • the 4-pyridinecarboxamide derivative represented by the formula (I) may exist as two geometric isomers derived from a carbon-carbon double bond contained in the structure,
  • the present invention includes each geometric isomer.
  • the present invention also includes a mixture containing the above-mentioned geometric isomer in an arbitrary ratio.
  • a solvent inert to the reaction can be widely used.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, halogenated solvents such as methylene chloride, 1,2-dichloroethane, chloroform, etc.
  • Hydrocarbon solvents examples include acetic acid such as nitrile solvents such as nitrile, aprotic polar solvents such as N-methylpyrrolidone and N, N′-dimethylimidazolinone. These solvents can be used alone or in combination of two or more as required.
  • Examples of the oxidizing agent used in the oxidation reaction of the compound represented by the formula (1-0) include m-chloroperbenzoic acid, sodium perelementate, and hydrogen peroxide. Such an oxidizing agent can be used in an amount of usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the 4-pyridinecarboxamide derivative represented by the formula (1-0). .
  • the reaction can usually be carried out within a range from ⁇ 78 ° C. to the boiling point of the solvent used, and the reaction is preferably carried out at 0 ° C. to room temperature.
  • the reaction time varies depending on the reaction temperature and cannot be generally specified, but the reaction is usually completed in about 0.5 to 24 hours.
  • the target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, distillation, etc. Further, it can be purified by ordinary purification means.
  • R 6 represents a C 1-6 alkyl group or a C 1-6 haloalkyl group
  • Y represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group or a trifluoromethanesulfonyloxy group.
  • C 1-6 alkyl group” and “C 1-6 haloalkyl group” of R 6 are the same as those defined “C 1-6 alkyl group” and "C 1-6 haloalkyl group” of R 2 It is.
  • solvents used in the reactions shown in Reaction Formulas 2-1 and 2-2 known solvents can be widely used as long as they are inert to the reaction.
  • ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, amide solvents such as N, N-dimethylformamide, solvents such as dimethyl sulfoxide, N-methylpyrrolidone, N, N′-dimethylimidazolinone can be mentioned.
  • solvents can be used alone or in combination of two or more as required.
  • base used in the reaction known inorganic bases and organic bases can be used.
  • alkali metal hydrides such as sodium hydride and potassium hydride
  • alkali metal carbonates such as sodium carbonate and potassium carbonate
  • alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide
  • potassium t- Alkali metal alkoxides such as butoxide, triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4- (N, N-dimethylamino) pyridine, N, N-dimethylaniline, N, N-diethylaniline, 1 , 5-diazabicyclo [4.3.0] non-5-ene, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,8-diazabicyclo [5.4.0] -7-undecene
  • organic bases such as (DBU).
  • the amount of the base used can be an amount that is usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, per 1 mol of the compound represented by the formula (1-3) or (2).
  • the reaction is preferably performed at 0 ° C. to the boiling point of the solvent used, more preferably at 0 ° C. to 80 ° C.
  • the reaction is usually completed in about 0.5 to 24 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. Moreover, it is also possible to use for the next reaction process, without isolating a target object from a reaction system.
  • M represents an alkali metal or hydrogen, and other symbols are as defined above.
  • the compound represented by the formula (1-0) is represented by the 4-pyridinecarboxamide derivative represented by the formula (3), which is a raw material compound for the reaction, and R 1 SM.
  • the thiol compound or thiol salt compound is produced according to the method described in Bioorganic Medicinal Chemistry Letters, 18 (9) 3307-3319 (2010), International Publication No. 2005/85216, or the like.
  • M of R 1 SM is hydrogen
  • a base is required for the reaction.
  • known inorganic bases and organic bases can be used, for example, alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, or alkaline earth metal carbonates.
  • alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide
  • alkali metal alkoxides such as potassium t-butoxide, triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4- ( N, N-dimethylamino) pyridine, N, N-dimethylaniline, N, N-diethylaniline, 1,5-diazabicyclo [4.3.0] non-5-ene, 1,4-diazabicyclo [2.2 .2] Octane (DABCO), 1,8-diazabicyclo [5.
  • DABCO 1,8-diazabicyclo [5.
  • DBU -7-undecene
  • organic bases such like.
  • the amount of the base used may be such that it is usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the compound represented by the formula R 1 SH.
  • solvents can be widely used. Examples thereof include amide solvents such as N, N-dimethylformamide, solvents such as dimethyl sulfoxide, N-methylpyrrolidone and N, N′-dimethylimidazolinone.
  • the reaction is preferably performed at 0 ° C. to the boiling point of the solvent used, more preferably at 0 ° C. to 100 ° C.
  • the reaction is usually completed in about 0.5 to 24 hours.
  • Z is preferably a fluorine atom or a chlorine atom.
  • the 4-pyridinecarboxamide derivative (3) or (1-0) represented by the above reaction formula 4-1 or the reaction formula 4-2 includes the aromatic amine compound represented by the above formula (4) and 4- It is produced from the pyridinecarboxylic acid derivative (5) or (6) according to the methods described in Bioorganic Medicinal Chemistry Letters, 24 (3) 983-988 (2014), International Publication No. 2012/130780, etc.
  • Examples of the condensing agent used in the reaction represented by Reaction Formula 4-1 or Reaction Formula 4-2 include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, N, N′-dicyclohexylcarbodiimide, N Carbodiimide condensing agents such as N'-diisopropylcarbodiimide, and triazine condensing agents such as 4- (4,6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorpholinium chloride. Can be used.
  • the amount of the condensing agent to be used may be such that it is usually 1 to 6 equivalents, preferably 1 to 2.5 equivalents, relative to the above-mentioned formula 4-pyridinecarboxylic acid derivative (5) or (6).
  • a catalyst can be used as necessary.
  • a catalyst 1-hydroxybenzotriazole, N, N-dimethylaminopyridine, triethylamine and the like can be used.
  • the amount of the catalyst used may be such that it is usually 0.01 to 1.0 equivalent, preferably 0.02 to 0.2 equivalent, relative to the formula 4-pyridinecarboxylic acid derivative (5) or (6).
  • solvents can be widely used as long as they are inert to the reaction.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, halogenated solvents such as methylene chloride, 1,2-dichloroethane, chloroform, etc.
  • Hydrocarbon solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, amide solvents such as N, N-dimethylformamide, N-methylpyrrolidone, N , N′-dimethylimidazolinone, dimethyl sulfoxide, pyridine and the like.
  • ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane
  • ester solvents such as methyl acetate and ethyl acetate
  • amide solvents such as N, N-dimethylformamide, N-methylpyrrolidone, N , N′-dimethylimidazolinone, dimethyl sulfoxide, pyridine and the like.
  • These solvents can be used alone or in combination of two or more as required.
  • the reaction is preferably performed at 0 °
  • the 4-pyridinecarboxamide derivative (3) or (1-0) represented by the above reaction formula 5-1 or reaction formula 5-2 is an aromatic represented by the above formula (4) in the presence of a base.
  • a base From an amine compound and a pyridine-4-carbonyl chloride derivative (7) or (8), according to the method described in Bioorganic Medicinal Chemistry Letters, 24 (13) 6693-6702 (2005), International Publication No. 2003/90912, etc. Manufactured.
  • solvent used in the reaction known solvents can be widely used as long as they are inert to the reaction.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, halogenated solvents such as methylene chloride, 1,2-dichloroethane, chloroform, etc.
  • Hydrocarbon solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amides such as N, N-dimethylformamide And aprotic polar solvents such as N-methylpyrrolidone, N, N′-dimethylimidazolinone, and pyridine. These solvents can be used alone or in combination of two or more as required.
  • known inorganic bases and organic bases can be used as the base used in the reaction.
  • Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrogen such as sodium hydride and potassium hydride. And the like.
  • Examples of the organic base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, and amines such as triethylamine, N, N-diisopropylethylamine, and pyridine. These bases may be used alone or in combination of two or more.
  • Such a base is usually used in an amount of 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the pyridine-4-carbonyl chloride derivative represented by the formula (7) or (8). obtain.
  • the reaction can be carried out usually within a range from ⁇ 78 ° C. to the boiling point of the solvent used, and it is preferable to carry out the reaction at 0 ° C. to 40 ° C.
  • the reaction time varies depending on the reaction temperature and cannot be generally specified, but the reaction is usually completed in about 0.5 to 24 hours.
  • n- represents normal
  • t- represents tertiary
  • i- represents iso
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • Bu represents a butyl group.
  • the compound of the present invention (including 4-pyridinecarboxamide derivative represented by the formula (1) and its N-oxide or a salt thereof, hereinafter the same) is used in agriculture, indoors, forests, livestock, hygiene, etc. It can be used to prevent or control organisms that cause harm in the scene. Therefore, the compound of the present invention can be used as an active ingredient of agricultural and horticultural agents, particularly agricultural and horticultural insecticides. Specific usage scenes, target pests, and usage methods are shown below, but the present invention is not limited to these.
  • the compound of the present invention can be used for agricultural crops such as food crops (rice, barley, wheat, rye, oats and other wheat, potatoes, sweet potatoes, potatoes, potatoes, potatoes, soybeans, red beans, broad beans, peas, etc. , Beans such as beans, peanuts, corn, persimmon, buckwheat, etc.), vegetables (cabbage, Chinese cabbage, radish, persimmon, broccoli, cauliflower, cruciferous crops such as komatsuna, pumpkin, cucumber, watermelon, mackerel, melon, Cucurbitaceae crops such as zucchini, yugao and garlic, eggplants such as eggplants, tomatoes, peppers, eggplants such as red pepper, shrimp, mushrooms such as ladle, red crustacean crops such as spinach and ducks, carrots, mitsuba and parsley Cereals such as celery, udon, asteraceae such as lettuce and burdock, leeks such as garlic, onion, green onion, leek Sparrows, shis
  • Lepidoptera from the arthropoda class eg, Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichodiaia choi)
  • Mamestra brassicae Spodoptera exigua, Spodoptera litura, etc.
  • Plutella xylostella Adakiphyceae apples honmai
  • Midarekamonmonaki Sacips fuscocupreanus
  • Chamonaki Homona magnanima
  • Chanohosoga Caloptilia theivora
  • Nashihimeshinshii Grapholita molesta
  • malinella peach leaf moth (Lyonetia cle) rkella, etc., Phylllocnistis citrella, etc., Hosomidae's Phyllonorycter ringoniella, etc.
  • Stathmopoda becomesssa, etc., Pectinophora gossypiella, etc., Cypridaceae (Carposina niponensis), etc. Monema flavecens), Hiloheria Oiraga (Parasa lepida), Himekuroiraga (Scopelodes contracus), etc.
  • Coleoptera eg, Anomala cuprea
  • bean squirrel Popillia japonica
  • Oxycetonia jucunda Anomala atageniculata, etc.
  • Ancholymaceae (Melanotus fortnumi), etc.
  • Aulacophora femoralis root worm species (Diabrotica spp.), Kiss beetle beetle (Phyllotreta striolata), beetle horn beetle (Cassida nebulosa), radish beetle (Phaedon brassicae), rice beetle moth (Oulema oryzae), pilican beetle Leptinotarsa decemlineata, etc., Rhynchites heros, etc., Cylas Adults, larvae and eggs of weevil (Anthonomus gradis grandis) is, Sphenophrus venatus vestitus, etc., such as Epuraea domina)
  • Heteroptera for example, Eurydema rugosum
  • Eysarcoris lewisi Eysarcoris parvus
  • Nymara viridae Nula Stink bug (Plautia stali)
  • Halymorpha mista etc.
  • Cletus ig punctiger etc.
  • Leptocorisa chinensis etc.
  • Mikame Apolygus spinolai
  • red streaks Kasumi turtle Stenotus rubrovittalus
  • Trigonotylus caelestialium Trigonotylus coelestialium
  • bean bug family circle stink bug Megacopta punctatissimum
  • Homoptera eg, Platypleura kaempferi
  • Arboridia ⁇ apicalis Empoasca onukii
  • eps ticc Empoasca onukii
  • Nephotettix virescens etc.
  • white lice Aleurocanthus spiniferus
  • silver leaf white lice Bemisia argentifolii
  • tobacco white lice Bemisia ⁇ tabaci
  • Grapes Trialeurodes vaporariorum
  • Radish aphids (Brevicoryne brassicae), citrus aphids (Toxopterarantaurantii), citrus aphids (Toxopteratriccitricidus), elder aphids (Aulacorthum magnoliae), nasid aphids (Schizaphis piricola) Aphids (Lipaphis erysimi), peach beetles (Hyalopterus pruni), chrysanthemum aphids (Pleotrichophorus chrysanthemi), chrysanthemum aphids (Macrosiphoniella sanborni), broad beetles (Megou) ra crassicauda), Ibara aphid (Sitobion ibarae), Tulip beetle aphid (Macrosiphum euphorbiae), Dwarf aphid (Myzus varians), Pe
  • Thysanoptera e.g., Thripscipalmi
  • Thrips tabaci Thrips tabaci
  • Thrips osa Yellow thrips Frankliniella occidentalis
  • Croton thrips Heliothrips haemorrhoidalis
  • Hymenoptera eg, Athalia rosae ruficornis
  • Arge pagana etc.
  • Arge mali etc.
  • Dryocsmus kuriphilus etc.
  • Barbet bees Megachile nipponica nipponica
  • other species of the antaceae Forma japonica
  • Giant giant ants Camponotus kiusiuensis
  • Black-headed ants Lasius fuliginosus
  • Fire ant Solenopsis richteri, S. invicta, S. invicta, S. minvicta, S. minvicta, etc.
  • Diptera e.g., Asphondylia yushimai
  • Rhacochlaena japonica Rhacochlaena japonica
  • Bactrocera cucurbitae etc.
  • Hola rel Drosophila suzukii and other species of the genus Derophila Liriomyza trifolii, tomato winged lily (Liriomyza sativae), Chromatomyia horticola, Agromyza ory, Agromyza ory Adults, larvae and eggs of the fly (Delia platura), the onion fly (Delia antiqua, etc.);
  • Orthoptera for example, locust locust (Locusta migratoria), grasshopper (Ruspolia lineosa), crickets (Teleogryllus emma), trochals (Truljalia hibinonis), gal rit ), Etc., adults, larvae and eggs of grasshoppers such as Oxya yezoensis;
  • Archaenioglossa eg, Pomacea canaliculata
  • Gastropoda eg, Plumonata
  • Achatina fulica slug of the slug family (Meghimatium bilineatum), Elephantaceae (Milax gagates), Leopmannina valentiana, Acusta despecta sieboldiana, etc .
  • Archaenioglossa eg, Pomacea canaliculata
  • Gastropoda eg, Plumonata
  • Achatina fulica slug of the slug family
  • Meghimatium bilineatum eghimatium bilineatum
  • Elephantaceae Meilax gagates
  • Leopmannina valentiana ecusta despecta sieboldiana, etc .
  • Tylenchida for example, Ditylenchus destructor of the family Angiogenidae, Tylenchorhynchus claytoni, for example, Pyllenaceae ), Southern nematode nematode (Pratylenchus coffeae), etc.
  • Nematode Ceronema jaejuense
  • Anguinaceae strawberry mesenchu Nothotylenchus acris
  • Aferenchoides strawberry nematode Aphelecchoides fragarriae, etc.
  • Examples include fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, Actinomycota, and the like.
  • the compound of the present invention works indoors in buildings including ordinary houses, and harms or corrupts wood and its processed wooden furniture, stored food, clothing, books, etc. It can also be used to control paw animals and fungi. Specific pests include:
  • Termites of the Arthropoda class of insects e.g., Coptotermesosaformosanus, Reticulitermes speratus
  • other termites of the genus Reticulitermes e.g., Coptotermesosaformosanus, Reticulitermes speratus
  • Other termites of the genus Reticulitermes e.g., Coptotermesosaformosanus, Reticulitermes speratus
  • Other termites of the genus Reticulitermes Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.
  • American termite Incisitermes minor
  • termite family termites Odontotermes formosanus
  • termite family Hodotermopsis jzponica lepidoptera termite larvae
  • Coleoptera for example, Sitophilus zeamais), Sitophilus zeamais, etc.
  • Physcomitridae Tribolium castaneum
  • Hirataka kunustomododoki Tribolium confusum
  • scallop slatted beetle Oryzaephilus surinamensis
  • scallop squirrel Cryptolestes pusillus
  • rioderma sera Stegobium paniceum
  • Attagenus unicolor japonicus Anthrenus verbasci, Dermestes maculatus, etc.
  • Lepidoptera for example, Cadra cautella
  • Ephestia kuehniella Plodia interpunctella, etc.
  • Sitotroga cerealella, etc. translucens Sitotroga cerealella, etc. translucens
  • adult moths larvae and eggs of the common oyster (Tineola bisselliella);
  • cockroach for example, Blattella germanica), cockroach (Periplaneta fuliginosa), cockroach (Periplaneta japonica, etc.);
  • Examples include adults, larvae and eggs of arthropod spider mites (for example, Tyrophagus putrescentiae, Lardoglyphus konoi, Carpoglyphus lactis, etc.).
  • the compounds of the present invention can also be used to control pests that damage or weaken trees in natural forests, artificial forests and urban green spaces.
  • Specific pests include:
  • Lepidoptera of Arthropoda eg, Calliteara argentata), Chadocuga (Euproctis pseudoconspersa), Orygiafur approximans, Euproctis subflava, Maiproga, Lymantria Species of the family (Malacosoma neustria testacea), Matsukareha (Dendrolimus spectabilis), Dendrolimus ⁇ superans, etc. (Ptycholoma lecheana circumclusana), Cridia kurokoi, Cydia cryptomeriae, etc., Sprigosoma imparilis, Hyphantria cunea, etc. Moth Department of Parasa Lepida (Parasa lepida), Himekuroiraga (Scopelodes contracus), adult Tenguiraga (Microleon longipalpis), etc.), larvae and eggs;
  • Coleoptera for example, Anomala rufocuprea
  • Heptophylla picea etc.
  • Agrilus spinipennis etc.
  • Basilepta pallidula etc. aceris
  • adults, larvae and eggs of the genus Rhizopertha dominica for example, Anomala rufocuprea
  • Heptophylla picea etc.
  • Agrilus spinipennis etc.
  • Basilepta pallidula, etc. aceris etc.
  • adults, larvae and eggs of the genus Rhizopertha dominica for example, Anomala rufocuprea
  • Heptophylla picea etc.
  • Agrilus spinipennis etc.
  • Basilepta pallidula etc. aceris
  • Stink bugs eg, Cinara todocola of Aphididae
  • Adelges japonicus Adelges japonicus
  • ceriferus a Stink bugs (eg, Cinara todocola of Aphididae), Adelges japonicus (Adelges japonicus), etc. ceriferus) etc) adults, larvae and eggs;
  • Flies for example, Tipula aino in the family Ganbo, Strobilomyia laricicola, etc., Contarinia inouyei, Contarinia matsusintome, etc. And eggs;
  • Linear animal genus genus Tylenoptera (for example, Bursaphelenchus xylophilus) Is mentioned.
  • the compounds of the present invention are arthropods that parasitize internally or externally to vertebrates, particularly domestic animals and pets such as cattle, sheep, goats, horses, pigs, poultry, dogs, cats and fish, which are warm-blooded vertebrates. It can also be used to prevent, treat or control animals, nematodes, flukes, tapeworms, and protozoa.
  • target animal species include rodents such as mice, rats, hamsters and squirrels, carnivores such as ferrets, avian pets such as ducks and pigeons, experimental animals, and the like.
  • Specific pests include:
  • Arthropod moths eg, Tabanus rufidens
  • Red-footed squirrel Tibanus chrysurus
  • Musca bezzii Musca domestica
  • Stomoxys calcitrans etc.
  • Gasterophilus intestinalis etc.
  • Hypodermaisbovis, etc. Oestrus ovis, etc.
  • Aldrichina grahami etc.
  • Lice for example, Haematopinidae suis), Boe lice (Daelinia bovis), etc. (Menopon gallinae etc.) adults, larvae and eggs;
  • Arthropod arachnid mites eg, Varroaobsjacobsoni
  • ticks Haemaphysalis longicornis
  • Yamato tick Ixodesophilovatus
  • Boophilus micrombly Takasago Ambula testudinarium
  • Mite family Ornithoyssus sylvialum etc.
  • Dermanyssus gallinae etc.
  • Coleoptera of linear animal gates eg, caterpillars, swine nematodes, swine lungworms, ciliate nematodes, bovine intestinal nodules, etc .; Roundworms (for example, swine roundworm, chicken roundworm, etc.); Phlegm reticulata (eg, Schistosoma japonicum, liver tetsu, deer buccal fluke, Westermann lung fluke, Japanese chicken egg fluke) Cestiidae (for example, foliate, expanded, Beneden, square, striate, and ringworm); Root flagellate (eg, Histomonas), Protoflagellate (eg, Leishmania, Trypanosoma, etc.), Polyflagellate (eg, Giardia, etc.), Trichomonas (eg, Trichomonas) ; Meat quality amoeba (for example, Entamoeba); Piroplasma subclasses
  • the compounds of the present invention can also be used to control pests that cause direct harm or discomfort to the human body, or to maintain public health for pests that carry or carry pathogens.
  • Specific pests include:
  • Lepidoptera of Arthropoda for example, Sphrageidus similis, etc., Kunugia undans, etc., Parasa consocia, etc., Artona martini Etc.) adults, larvae and eggs;
  • Coleoptera for example, Xanthochroa waterhousei, etc.
  • Epicauta gorhani etc.
  • larvae of Paederus fuscipes and adults such as Paederus fuscipes, etc.
  • flies eg, Armygeres subalbatus
  • Cronicoides nipponensis, etc. Chironomus yoshimatsui, etc.
  • Simulium nikkoense etc.
  • Hirosia humilis Musca domestica, etc.
  • Fannia canicularis etc.
  • Phormia regina etc., such as Srinaph Adult larvae, eggs and eggs;
  • cockroach for example, Blattella ⁇ germanica
  • cockroach's American cockroach Periplaneta fuliginosa
  • cockroach Periplaneta japonica
  • Anemone of annelids for example, Haemadipsa zeylanica japonica Is mentioned.
  • the compounds of the present invention are particularly valuable for controlling pests that damage crops, natural forests, artificial forests, urban greenery trees and ornamental plants, such as arthropods, gastropods and nematodes.
  • the compounds of the present invention may be used in other commercially active formulations, such as insecticides, acaricides, nematicides, fungicides, in their commercially useful formulations and use forms prepared by these formulations. It can also be present as a mixture with agents, synergists, plant regulators, baits or herbicides.
  • the compound of the present invention can be used as it is or in a form generally usable as an agrochemical, such as a wettable powder, a granular wettable powder, a dry flowable powder, an aqueous solvent, an emulsion, a liquid, an oil, an aqueous suspension and an aqueous emulsion. It can be used in dosage forms such as flowables, capsules, powders, granules, fine granules, baits, tablets, sprays, fumes, aerosols and the like. In these preparations, the total amount of the active ingredient compounds is usually 00.1 to 99.9% by mass, preferably 0.2 to 90% by mass.
  • various agricultural chemical adjuvants conventionally used in the technical field of agricultural and horticultural medicine can be appropriately used.
  • Such agrochemical adjuvants can be used for the purpose of, for example, improving the effects, stabilizing, and improving dispersibility of agricultural and horticultural chemicals.
  • the agricultural chemical adjuvant include a carrier (diluent), a spreading agent, an emulsifier, a wetting agent, a dispersing agent, a disintegrating agent, and the like.
  • Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methyl Mention may be made of naphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like.
  • solid carrier clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.
  • ordinary surfactants can be used, for example, higher alcohol sodium sulfate, stearyl trimethyl ammonium chloride, polyoxyethylene alkyl phenyl ether, anionic surfactants such as lauryl betaine, Cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used.
  • spreading agents wetting agents such as dialkyl sulfosuccinate; fixing agents such as carboxymethyl cellulose and polyvinyl alcohol; disintegrating agents such as sodium lignin sulfonate and sodium lauryl sulfate can be used.
  • the compound of this invention can also be mix
  • the content of the compound of the present invention as an active ingredient is, for example, 0.01 to 99.9% by mass, and preferably selected from the range of 0.2 to 90% by mass.
  • an emulsion it can be produced so as to contain an active ingredient of about 1 to 90% by weight, preferably 10 to 40% by weight.
  • the foliage of the plant against the place where damage by these pests or where damage is likely to occur In addition to spraying on the soil, it can be applied to the soil, etc., by mixing it with the soil, etc., soil 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 used after being absorbed. It can also be used by soaking seeds in chemicals, seed dressing, seed treatment such as calper treatment, application to nutrient solution in nutrient solution (hydroponic) cultivation, smoke, or trunk injection.
  • the preparation is not diluted or diluted in water.
  • Method of applying to plant stock or seedling nursery, etc., spraying granules to plant stock or nursery for seedling, powder, wettable powder, granular water before sowing or transplanting A method of spraying Japanese sweets, granules, etc. and mixing with the whole soil, before sowing or planting plants, planting holes, crops etc., powder, wettable powder, granule wettable powder, granules, fine granules, The method of spraying etc. is mentioned.
  • wettable powders For wettable powders, granular wettable powders, aqueous solvents, emulsions, liquids, flowables such as suspensions in water and emulsions in water, capsules, etc., dilute with water and generally apply 5 to 500 liters per 10 ares.
  • powder, granule, fine granule or bait, etc. it should be spread evenly over the entire area to be treated. What is necessary is just to spread on the soil surface. Spraying or irrigation may be around the seeds, crops or trees that you want to protect from harm. Further, the active ingredient can be mechanically dispersed by tilling during or after spraying.
  • the dosage form may differ depending on the time of application such as application at seeding, greening period, application at transplanting, etc., for example, powder, granule wettable powder, granule, fine powder What is necessary is just to apply in dosage forms, such as a granule. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder, granules or fine granules, for example, mixed with floor soil, mixed with soil, mixed into the entire soil, etc. it can. Alternatively, the culture medium and various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, pack agents, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate preparation 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.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted to immerse the seed in a liquid state to attach and permeate the drug, and a solid preparation or liquid preparation is mixed with the seed.
  • a method of dressing and adhering to the surface of the seed examples thereof include a method of dressing and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as a resin and a polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, nutrition for bulbs, tubers, seed buds, buds, baskets, bulbs or cuttings cultivation Mention may be made of plants for breeding.
  • the “soil” or “cultivation carrier” of a plant when applied refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. Any material can be used as long as it can grow, so-called soil, seedling mat, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel material, polymer material, rock Examples include wool, glass wool, wood chips, and bark.
  • the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferable.
  • the compounds of the present invention are also valuable for protecting wood (standing trees, fallen trees, processed wood, storage wood or structural wood) from insulting insects such as termites or cucumbers and fungi.
  • insecticides such as termites or cucumbers and fungi.
  • oils, emulsions, wettable powders, powders, etc. used in this scene are mixed with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists.
  • the total amount of active ingredient compounds is 0.0001 to 95% by mass, preferably 0.005 to 10% by mass for oils, powders and granules, emulsions, wettable powders and sols. May contain 0.01 to 50% by mass.
  • When controlling arthropods or fungi apply 0.01 to 100 g of active ingredient compound per 1 m 2 to the soil or wood surface.
  • the compounds of the present invention can be used when storing products such as cereals, fruits, nuts, spices and tobacco as they are, in a powdered state, or mixed in the product. It can be used to protect against fungal damage.
  • animals skin, hair, wool, feathers, etc.
  • plant products cotton, paper, etc.
  • Lepidoptera, Coleoptera, Spots and Cockroaches It can be protected, and can be protected from attacks by Lepidoptera, Coleoptera, flies and ticks when storing food such as meat and fish.
  • spraying oils, emulsions, wettable powders, powders, etc., installing resin transpiration agents, treating smoke and fumes, installing granules, tablets and poison baits, spraying aerosols, etc. Can be controlled with.
  • These formulations can also be present as a mixture with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, in these formulations. May contain 0.0001 to 95% by mass of the total amount of active ingredient compounds.
  • the compounds of the present invention prevail or mediate diseases of arthropods, humans and livestock that parasitize the body surface of humans and livestock, causing direct harm such as eating or sucking skin. It is valuable for the control or prevention of arthropods, nematodes, flukes, tapeworms, protozoa, and arthropods that cause discomfort to humans.
  • the compound of the present invention is mixed in a small meal or feed, or a suitable pharmaceutical composition that can be taken orally, such as tablets, pills containing pharmaceutically acceptable carriers and coating substances, Capsules, pastes, gels, beverages, medicinal feeds, medicinal drinking water, medicinal supplements, sustained-release large pills, other sustained-release devices designed to be retained in the gastrointestinal tract, sprays, powders, It can be administered transdermally as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like.
  • the active ingredient compound is generally contained in the preparation in an amount of 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass.
  • a device for example, a collar, a medallion, an ear tag, or the like
  • a device for example, a collar, a medallion, an ear tag, or the like
  • the beverage When administered orally as a medicinal beverage, the beverage is usually a suspension, humectant or other excipient such as bentonite, a suitable non-toxic solvent or water solution, suspension or dispersion. .
  • beverages also contain an antifoam agent.
  • Beverage formulations generally contain 0.01 to 1.0% by weight, preferably 0.01 to 0.1% by weight, of the active ingredient compound.
  • capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used.
  • These forms of use are obtained by intimately mixing the active ingredient with suitably finely divided diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. Manufactured.
  • Such unit use formulations can vary widely in the weight and content of the anthelmintic depending on the type of host animal to be treated, the degree of infection and the type of parasite and the body weight of the host.
  • the active ingredient compound When administered by animal feed, the active ingredient compound can be homogeneously dispersed in the feed, used as a top dressing or in the form of pellets.
  • the active ingredient compound is contained in the final feed in an amount of 0.0001 to 0.05% by mass, preferably 0.0005 to 0.01% by mass.
  • Dissolved or dispersed in a liquid carrier vehicle can be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection.
  • the active compounds are preferably mixed with suitable vegetable oils, such as peanut oil, cottonseed oil.
  • suitable vegetable oils such as peanut oil, cottonseed oil.
  • Such a formulation generally contains 0.05 to 50% by mass, preferably 0.1 to 5.0% by mass of the active ingredient compound.
  • the active ingredient compound can be locally administered by mixing with an appropriate carrier such as dimethyl sulfoxide or a hydrocarbon solvent.
  • This formulation is applied directly to the external surface of the animal by spraying or direct injection.
  • the compound of the present invention can be used as an anthelmintic agent for arthropods that cause direct harm, or as an anthelmintic agent for arthropods that are mediators of diseases, as an oil agent against the surrounding environment in which these pests can be latent.
  • Spraying injecting, irrigating and coating of emulsions, wettable powders, spraying of powders, fumigants, mosquito coils, self-combustion smoke chemicals, chemical reaction type aerosols, fogging, etc.
  • methods such as treatment of smoke, ULV, etc., installation of granules, tablets and poisonous bait, or addition of floating powder, granules, etc.
  • the preparations in these use forms can exist as a mixture with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists.
  • the active ingredient compounds are contained in a total amount of 0.0001 to 95% by mass.
  • the compound of the present invention can be present as a mixture with other active compounds.
  • active compounds include the following:
  • Organophosphorus agents eg, acephate, azinphos-methyl, chlorpyrifos, diazinon, dichlorvos, dimeton-S-methyl, dimethoate, Dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monocrotophos (methidathion) monocrotophos, naled, oxydeprophos, oxideprofos, parathion, phenthoate, phostho, pirimiphos-methyl, pyridafenthion, profenofos (pr) ofenofos, prothiofos, propaphos, pyraclofos, salithion, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, bamidothion etc);
  • Carbamate agents eg, alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furothiocarb
  • Organic chlorinating agents for example, aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane, etc.
  • Pyrethroids eg, acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin, deltamethrin) deltamethrin
  • etofenprox fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalinate, furamethrin, halofen Proxrin (halfenprox), imiprothrin permethrin, phenothrin, prallethrin, pyrethrin, resmethrin, silafluo E emissions (silafluofen), tefluthrin (tefluthrin), tralomethrin (tralomethrin), transfluthrin (Transfluthrin), etc.);
  • Neonicotinoid agents for example, acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc.
  • Diamide agents for example, chlorantraniliprore, cyantraniliprore, cyclaniliprore, tetraniliprole, flubenziamid, etc.
  • Insect growth control agents such as benzoyl urea (eg, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron) ), Lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, cyromazine, etc.);
  • Phenylpyrazole agents for example, ethiprole, fipronil, acetoprole, pyrafluoprole, pyriplore, etc.
  • Nereistoxin agents for example, bensultap, cartap, thiocyclam, thiosultap, etc.
  • Diacyl hydrazone agents for example, chromafenozide halofenozide, methoxyfenozide, tebufenozide
  • Juvenile hormone agents eg, diofenolan, phenoxycarb, hydroprene, metoprene, pyriproxyfen, etc.
  • Insecticidal substances produced by microorganisms for example, abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, nikkomycin
  • Polyoxin complex polioxin
  • spinetram spinosad
  • BT agent Bacillus thuringiensis and insecticidal protein product
  • Insecticides derived from natural products for example, anabasine, azadiractin, deguelin, fatty acid glycerides (decanolyoctanoylglycerol), hydroxypropyl starch, soy lecithin, nicotine) ), Nornicotine, oreic acid sodium salt, machine oil (petroleum oil), propylene glycol monolaurate, rape oil, rotenone, sorbitan fatty acid ester ( Sorbitan fatty acid ester), starch, etc .;
  • Other insecticides include, for example, afidopyropen, broflanilide, chlorfenapyr, diafenthiuron, dicfenomezotiaz, dicloromezotiaz, DBEDC (dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt (Flonicamid), flometoquin, flufenerim, fluhexafon
  • Acaricides for example, acequinocyl, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromolate, bromopropylate, Quinomethionat, clofentezine, cyenopyrafen, cyflumetofen, tricyclohexyltin hydroxide, dicofol, dienochlor, diflovidazin, oxa , Fenazaflor, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacriprim (fluac) rypyrim, hexythiazox, pyrimidifen, polynactins, propargite, pyflubumide, pyridaben, spirodiclofen, spiromesifen, spiromesifen (Tebufenpyrad
  • Nematicides eg, aluminum phosphide, benclothiaz, cadusafos, etoprophos, fluensulfone, fluopyram, fosthiazate, furfural
  • Imicyafos levamisol hydrochloride, mesulfenfos, metam-ammonium, methylisocyanate, moranteltartarate, oxamyl, thifluzamide, thifluzamide thioxazafen
  • Poisonous baits eg, chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin, etc.
  • the compound of the present invention can be present as a mixture with other active compounds other than the compound having insecticidal activity, acaricidal activity or nematicidal activity. In order to control diseases and / or weeds that occur at the same time of use, it can be used in combination with a compound having fungicidal activity, herbicidal activity, or plant growth regulating activity, thereby reducing the control effort and reducing the dosage. Synergistic effects can be expected. Moreover, more effective control effects, such as a synergistic effect, can be expected by using a mixture with a repellent or a synergist.
  • active compound examples include the following fungicides:
  • Bactericides that inhibit nucleic acid synthesis eg, benalaxyl, benalaxyl m, belalaxyl, metalaxyl, metalaxyl m, metalaxyl m, oxadixyl, ofurace, buprimate
  • Bopirimate dimethirimol, dimethirimol, ethirimol, hydroxyioxazole, hymexazol, octillinone, oxolinic acid, etc.
  • Bactericides that inhibit respiration eg, diflumetorim, tolfenpyrad, tebufenpyrad, fenazaquin, pyridaben, fenpyroximate, pyrimidifone, rotenidone) benodanil
  • flutolanil mepronil
  • isofetamid fluopyram
  • fenfuram carboxin
  • oxycarboxin thiofluzamide
  • benzobindiflupyr Benzovindiflupyr
  • bixafen fluxapyroxad, furametpyr
  • isopyrazam penflufen, penthiopyrad, sedaxane sedaxane, boscalid
  • pyraziflumide azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin ), Pyraoxystrobin, pyraclostrobin, pyrametostrobin,
  • Bactericides that inhibit amino acid and protein synthesis eg, andoprim, cyprodinil, mepanipyrim, pyrimethanil, blasticidin s, kasugamycin, streptomycin) ), Oxytetracycline, mildiomycin, etc.;
  • Bactericides that inhibit signal transduction eg quinoxyfen, proquinazid, fenpiclonil, fludioxonil, fludioxonil, chlozolinate, iprodione, procymidone, clocloolin, etc.
  • Bactericides that inhibit lipid and cell membrane synthesis eg, edifenphos, iprobenfos, pyrazophos, isoprothiolane, biphenyl, chloroneb, quintozene, technazen, torquelophos Methyl (tolclofos-methyl), echlomezole, iodocarb, propamocarb, prothiocarb, etc.
  • lipid and cell membrane synthesis eg, edifenphos, iprobenfos, pyrazophos, isoprothiolane, biphenyl, chloroneb, quintozene, technazen, torquelophos Methyl (tolclofos-methyl), echlomezole, iodocarb, propamocarb, prothiocarb, etc.
  • Bactericides that inhibit cell membrane sterol biosynthesis eg, triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazalil, oxpoconazole, Pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole , Epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, fluotrimazole, full Conconazole (furconazole), flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole propiconazole), simeconazole, tebuconazole, tetraconazole, triadimef
  • Bactericides that inhibit cell wall biosynthesis eg, validamycin, polyoxin, dimetomorph, flumorph, pyrimorph, benchthiavalicarb, iprovalicarb, valenarate (Valifenalate), mandipropamid, etc.
  • bactericides that inhibit cell wall melanin synthesis for example, fthalide, pyroquilon, tricyclazole, carpropamid, diclocymet, phenoxanil etc);
  • Fungicides that induce host plant resistance eg, probenazole, thiadinil, isothianil, laminarin, extract of from giant-knotweed, acibenzolar-s -methyl
  • Bactericides that inhibit multiple action points eg copper, dbedc (complexcomofbis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid)), cupric hydroxide (copper hydroxide), copper nonylphenol sulfonate (copper) nonylphenol sulfonate, basic copper oxychloride, basic copper sulfate, organic copper (oxine-copper), sulfur, lime sulfur compound (calcium polysulfide), silver (silver), dd (1,3-dichloropropene), dazomet, methyl bromide, methylisothiocyanate, metam-ammonium, mancozeb, maneb, metiram , Propineb, thiram, zinc sulfate (zincinesulfate), zineb, ziram, captan, captafol, folpet ), Chlorothalonil, dichlofluanid, tolyl
  • fungicides eg, cymoxanil, fosetyl, phosphoric acid, phosphite, tecloftalam, triazoxid, flusulfamide, dichromedin ( diclomezine, metasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, flutianil, ferimzone, oxathiapiprolin, oxathiapiprolin, oxathiapiprolin tolprocarb), picarbutrazox, wo2005081174, wo2011811742, machine oil (petroleum oil), organic oil (organic oil), potassium hydrogen carbonate (potassium hydrogen carbonate), sodium hydrogen carbonate (sodium hydrogen carbonate), hypochlorous acid Sodium salt (sodi um hypochlorite, calcium carbonate, benthiazole, diclobutrazol, flumetover, thiadiazin, dichlone, organotin (organo-t
  • Examples of compounds having herbicidal activity include aclonifen, acifluofen n-sodium, alachlor, alloxydim, amicarbazone, amidosulfuron, anilophos ( anilofos, asuram, atrazine, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, Benzofenap, bialaphos, bifenox, bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide, calcium peroxide Rubetamid (carbetamide), cinosulfuron (cinosulfuron), clomeprop (clomeprop), cyclosulfamuron (cyclosulfamuron), cyhalofop-butyl, daimuron (daimuron), desmedipham (desmedipham), diclohop methyl (diclofop)
  • the compound of the present invention is a compound having a plant growth regulating action (for example, 1-naphthylacetic amide acid (1-naphthylacetic acid), 4-CPA (4-CPA), benzylaminopurine, butralin, Calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, Daminozide, decyl alcohol, dichlorjoprop, ethephon, etychlozate, flurprimidol, forclorfenuron, gibberellic acid , Indolebutyric acid, male Potassium hydrazide (maleic hydrazide potassium salt), mefenpyr (mefenpyr), mepiquat chloride, oxine) sulfate, -hydroxyquinoline sulfate, paclobutrazol, paraffin , Prohexadione-calcium, prohydrojas
  • the compounds of the present invention are:
  • Repellents eg capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene
  • Linalool menthol
  • menthone naphthalene
  • thiram etc.
  • Synergists eg, methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl) phthalimide
  • phenyl salioxon piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, valbutin etc
  • It can also be used as a mixture.
  • the compound of the present invention is a biological pesticide, for example, cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopox virus, EPV), granulosis virus (Granulosis virus, GV), nuclear polyhedrosis virus (Nuclear) virus preparations such as polyhedrosisVvirus ⁇ (NPV), Beauveria bassiana, Beauveria brongniartii, Monocrosporium phymatophagum, Paeciloosepas , Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc.
  • CPV cytoplasmic polyhedrosis virus
  • Entomopox virus Entomopox virus
  • EPV granulosis virus
  • GV nuclear polyhedrosis virus
  • Nuclear virus preparations such as polyhedrosisVvirus ⁇ (NP
  • Microbial pesticides used as insecticides or nematocides Agrobacterium radiobactor, Bacillus subtilis, nonpathogenic Erwinia carotovora, nonpathogenic Fusarium oxysporum ), Pseudomonas CAB-02 (Pseudomonas fluorescens), Talaromyces ⁇ ⁇ , Trichoderma atroviride, Trichoderma lignolan Similar effects can be expected when used in combination with microbial pesticides, biopesticides used as herbicides such as Xanthomonas campestris.
  • biological pesticides for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes adi, Aphidoletes adi Chrysoperia carnea), Dacnusa sibirica, Diglyphus isaea, Oncarsia formosa, Eretmocerus eremicus, Hen rid Crested bee (Hemiptarsenus varicornis), Scarlet winged bee (Neochrysocharis formosa), Scarlet beetle (Orius sauteri), Scarlet beetle (Orius strigicollis), Phytosei mite (Phytosei natural enemies such as ulus persimilis, black leopard turtle (Pilophorus typicus), piocoris varius, etc., codlelure, cuelure, geraniol
  • Example 1-1 Synthesis of 3-fluoro-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: B-1) 3-Fluoro-pyridine-4-carboxylic acid (0.50 g), 2- To a solution of amino-5-trifluoromethylpyridine (0.60 g) and 1-hydroxybenzotriazole monohydrate (54 mg) in pyridine (8 ml), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride ( 0.95 g) was added at room temperature, and the mixture was stirred at room temperature for 3 hours.
  • Example 1-2 Synthesis of 3-ethylsulfanyl-N- (5-trifluoromethylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-3) 3-Fluoro-N- (5-trifluoromethylpyridine-2- Yl) -4-pyridinecarboxamide (0.57 g) in N, N-dimethylformamide (4 ml) was added sodium ethanethiolate (0.26 g) at room temperature and stirred at room temperature for 2 hours. Ethyl acetate and water were added to the reaction solution, the organic layer was separated, and the organic layer was further washed with water.
  • Example 4 3-ethylsulfonyl-N-ethyl-N- (5-trifluoromethanesulfonylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-155) and 3-ethylsulfonyl-N-ethyl-N- (5 Synthesis of -trifluoromethanesulfinylpyridin-2-yl) -4-pyridinecarboxamide (Compound No .: A-156) 3-Ethylsulfonyl-N-ethyl-N- (5-trifluoromethylthiopyridin-2-yl) -4 -To a solution of pyridinecarboxamide (0.70 g) in acetonitrile (7 ml), sodium tungsten (IV) dihydrate (30 mg) was added at room temperature.
  • aqueous hydrogen peroxide 14 ml was added to the reaction mixture at room temperature, and the mixture was stirred at 65 ° C. for 3 hr. Ethyl acetate, water and sodium sulfite were added to the reaction mixture and stirred. After separating the organic layer, the organic layer was further washed with water. The organic layer was dried over anhydrous magnesium sulfate, and then the organic solvent was distilled off under reduced pressure.
  • Emulsion Compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts) and Solpol 3005X (mixture of nonionic surfactant and anionic surfactant, Toho Chemical Industry Co., Ltd. (trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 2 Hydrating Agent-1 Compound of the present invention (20 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (10 parts), Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (60 parts) Sun extract P-252 (sodium lignin sulfonate, Nippon Paper Chemical Co., Ltd., trade name) (5 parts) and Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Co., Ltd., trade name) (5 parts) was uniformly mixed and ground with an air mill to obtain a wettable powder.
  • Nipseal NS-K white carbon, Tosoh Silica Co., Ltd., trade name
  • Kaolin clay Kaolin clay
  • Sun extract P-252 sodium lignin sulfonate, Nippon Paper Chemical Co., Ltd., trade name
  • Lunox P-65L alkyl allyl sulfonate, To
  • Formulation example 3 wettable powder-2 Compound of the present invention (20 parts), Nipsil NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (20 parts), Kaolin clay (50 parts), LUNOX 1000C (naphthalene sulfonate condensate, Toho Chemical) Kogyo Co., Ltd. (trade name) (5 parts) and Solpol 5276 (nonionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts) were uniformly mixed and pulverized in an air mill to obtain a wettable powder. Obtained.
  • Formulation Example 4 Aqueous solvent-1 Compound (20 parts) of the present invention, Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (3 parts), water-soluble carrier (potassium chloride) (77 parts) are uniformly mixed and pulverized Thus, an aqueous solvent was obtained.
  • Lunox P-65L alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name
  • water-soluble carrier potassium chloride
  • Formulation Example 5 Aqueous solvent-2 Uniformly mix the compound of the present invention (50 parts), Newkalgen BX-C (Na alkylnaphthalene sulfonate, Takemoto Yushi, trade name) (5 parts), silicon dioxide (2 parts) and water-soluble carrier (43 parts) The mixture was pulverized to obtain an aqueous solvent.
  • Newkalgen BX-C Na alkylnaphthalene sulfonate, Takemoto Yushi, trade name
  • silicon dioxide 2 parts
  • water-soluble carrier 43 parts
  • Formulation Example 6 Flowable Agent-1 Premixed propylene glycol (5 parts), Solpol 7933 (anionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts) and water (50 parts) to the compound of the present invention (20 parts) ) was dispersed into a slurry mixture, and this slurry mixture was wet pulverized with Dynomill (Shinmaru Enterprises Co., Ltd.), and then xanthan gum (0.2 parts) was mixed and dispersed well in water (19.8 parts) in advance. Things were added to obtain a flowable agent.
  • Formulation Example 7 Flowable agent-2 Compound of the present invention (20 parts), Newkalgen FS-26 (mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), propylene glycol (8 parts) and Water (50 parts) was mixed in advance, and this slurry-like mixture was wet-pulverized with a Dynomill (Shinmaru Enterprises). Next, xanthan gum (0.2 parts) was thoroughly mixed and dispersed in water (16.8 parts) to prepare a gel-like material, which was thoroughly mixed with the pulverized slurry to obtain a flowable agent.
  • Newkalgen FS-26 mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name
  • propylene glycol 8 parts
  • Water 50 parts
  • xanthan gum 0.2
  • Formulation Example 8 Emulsion formulation-1 Mixing and homogenizing the compound of the present invention (20 parts) with Solpol CA-42 (nonionic activator, Toho Chemical Co., Ltd., trade name) (15 parts) and preservative Proxel GX-L (0.1 parts) Then, water (59.6 parts) was gradually added with stirring to obtain a dispersion. Antifoam anti-home E-20 (emulsion type modified silicone, Kao Corporation, trade name) (0.1 part) was added to the resulting dispersion, and xanthan gum dispersed in propylene glycol (5.0 parts) (0.2 parts) was added to obtain an emulsion formulation (phase inversion emulsification method).
  • Solpol CA-42 nonionic activator, Toho Chemical Co., Ltd., trade name
  • preservative Proxel GX-L 0.1 parts
  • Emulsion formulation-2 The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with the surfactant Rheidol 430V (polyoxyethylene sorbite tetraoleate, Kao Corporation, trade name) (24 parts). In water (50.6 parts), the resulting liquid, antifoam anti-home E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part) and preservative Proxel GX-L ( 0.1 part) was added and dispersed using a homogenizer, and xanthan gum (0.2 part) dispersed in propylene glycol (5.0 parts) was added to obtain an emulsion formulation (mechanical emulsification method) .
  • Rheidol 430V polyoxyethylene sorbite tetraoleate, Kao Corporation, trade name
  • Microemulsion-1 The compound of the present invention (0.01 part) and Solpol CA-42 (nonionic activator, Toho Chemical Co., Ltd., trade name) (0.1 part) were mixed and homogenized, and then gradually mixed with stirring. (99.79 parts) was added. Preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.
  • Formulation Example 12 ME agent-3
  • the compound of the present invention (0.01 part) was mixed with solvent Solvesso 200 (0.08 part), Neukalgen ST-30 (polyoxyethylene arylphenyl ether formaldehyde condensate, polyoxyalkylene arylphenyl ether, alkylbenzene sulfonate, and xylene.
  • solvent Solvesso 200 (0.08 part)
  • Neukalgen ST-30 polyoxyethylene arylphenyl ether formaldehyde condensate, polyoxyalkylene arylphenyl ether, alkylbenzene sulfonate, and xylene.
  • the mixture Takemoto Yushi Co., Ltd., trade name
  • the mixture was mixed with a surfactant, homogenized, and water (99.69 parts) was gradually added while stirring.
  • Preservative Proxel GX-L (0.1 part) was added to the dispersion to obtain a microemulsion.
  • Formulation Example 13 Granule-1
  • the compound of the present invention (5 parts), bentonite (30 parts), clay (60 parts) and sodium lignin sulfonate (5 parts) were uniformly pulverized and mixed, mixed well with water, extruded and granulated, Granules were obtained by dry sizing.
  • Formulation Example 14 Granule-2 After putting silica sand (90 parts) in a rolling granulator and containing water, the compound of the present invention (5 parts), sodium lignin sulfonate (4 parts), polyvinyl alcohol (PVA) (PVA) ( 0.5 parts) and white carbon (0.5 parts) were added and coated, and then dried and sized to obtain granules.
  • the compound of the present invention 5 parts
  • sodium lignin sulfonate 4 parts
  • PVA polyvinyl alcohol
  • white carbon 0.5 parts
  • Formulation Example 15 Granule-3 Ishikawa Light (89 parts) was placed in a rolling granulator and water-containing, and then the compound of the present invention (5 parts), sodium lignin sulfonate (3 parts), and dioctyl sulfosuccinate sodium previously pulverized and mixed. (0.5 parts), POE styryl phenyl ether (2 parts) and polyvinyl alcohol (PVA) (0.5 parts) were added, coated, and then dried to obtain granules.
  • the compound of the present invention 5 parts
  • sodium lignin sulfonate 3 parts
  • dioctyl sulfosuccinate sodium previously pulverized and mixed 0.5 parts
  • POE styryl phenyl ether (2 parts) and polyvinyl alcohol (PVA) 0.5 parts
  • Formulation Example 16 Fine granule-1
  • the compound of the present invention (2 parts) was diluted with a solvent, and mixed with pumice (98 parts) as an extender while spraying the diluent.
  • the obtained granular composition was dried and sieved to obtain a fine granule.
  • Formulation Example 17 Fine granule-2
  • the compound of the present invention (5 parts) was subjected to air mill grinding or mechanochemical grinding as required.
  • the powdery base and silica sand (85 parts) as an extender were uniformly mixed, and then mixed with spraying the binder Toxanone GR-31A (10 parts) diluted with a solvent, and the resulting granular composition was dried. Thereafter, it was sieved to obtain a fine granule.
  • Formulation Example 18 Powder A compound of the present invention (5 parts), white carbon (5 parts), and clay (trade name, Nippon Talc Co., Ltd.) (90 parts) were uniformly mixed and ground to obtain a powder.
  • Formulation Example 19 DL powder A compound (5 parts) of the present invention, propylene glycol (0.5 part) and DL clay (94.5 parts) were uniformly mixed and ground to obtain a powder.
  • Formulation Example 20 Seed coating powder Compound (10 parts) of the present invention, sodium lignin sulfonate (6 parts), polyvinyl alcohol (PVA) (1 part) and clay (Nippon Talc Co., Ltd. trade name) (83 parts) A powder prepared by uniformly mixing and pulverizing was mixed with seeds previously wetted, and air-dried to obtain coated seeds.
  • Example 4 Next, the action effect and usefulness of the compound of the present invention will be described with specific test results.
  • the compound used for comparison (Comparative Example A) was described in Example 17 of JP-A-5-32631 and was a compound having the following structure.
  • Test Example 1 Insecticidal effect test by spraying treatment on cucumber cotton aphid (Aphis gosiipii Glover) Leaf pieces infested with 50 to 80 aphid adult larvae were inoculated into the leaves of pot-planted cucumber seedlings grown for 2 weeks after sowing. . On the day after the inoculation, the chemical solution adjusted to 500 ppm was sprayed onto the leaf stems of cucumber seedlings infested with aphids using an air brush. Seven days after the treatment, the number of parasitic aphids was examined, and the control rate was calculated according to the following formula. The test was conducted using 1 seedling in each group.
  • Control rate (%) (1 ⁇ A / B ⁇ D / C) ⁇ 100
  • A Number of aphid adult larvae before spraying in the untreated area per seedling
  • B Number of adult aphids before spraying in the treated area per seedling
  • C Number of adult aphids 7 days after spraying in the untreated area per seedling
  • D Per seedling Aphid adult larvae 7 days after spraying in the treatment area
  • Test Example 2 Insecticidal effect test by irrigation treatment on cucumber cotton aphid (Aphis gosiipii Glover) Inoculated 50 to 80 leaves of aphid adult larvae onto the leaves of potted cucumber seedlings grown for 2 weeks after sowing . On the day after the inoculation, the chemical solution prepared to 500 ppm was irrigated to the stock of the cucumber seedlings infested with aphids. Seven days after the treatment, the number of parasitic aphids was examined, and the control rate was calculated according to the following formula. The test was conducted using 1 seedling in each group.
  • Control rate (%) (1 ⁇ A / B ⁇ D / C) ⁇ 100
  • A Number of aphid adult larvae before spraying in the untreated area per seedling
  • B Number of adult aphids before spraying in the treated area per seedling
  • C Number of adult aphids 7 days after spraying in the untreated area per seedling
  • D Per seedling Aphid adult larvae 7 days after spraying in the treatment area
  • Test Example 3 Test of egg-killing effect on beetle tobacco whitefly (Bemisia tabaci Gennaius) Spawned. A leaf disc was made from the spawned primary bean leaves and placed on a moistened absorbent cotton so that the leaf back (spawning surface) was on top. The chemical solution prepared to a predetermined concentration was sprayed on the leaf disk using an air brush.
  • Each of the 152, A-153, A-154, A-155, A-156, A-175, A-178, A-180 and A-185 compounds showed a control rate of 90% or more.
  • the control rate of the compound of Comparative Agent A was 0%.
  • the present invention can be used in the field of agriculture and horticulture.

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

Abstract

La présente invention concerne un composé qui est excellent en tant que principe actif pour des agents agricoles et horticoles. Plus précisément, la présente invention concerne le dérivé 4-pyridinecarboxamide représenté par la formule (1) [dans la formule, R1 représente un groupe alkyle en C1-6 ou un groupe halogénoalkyle en C1-6 ; R2 représente un atome d'hydrogène, un groupe alkyle en C1-6 ou un groupe halogénoalkyle en C1-6 ; G1, G2, G3, G4 et G5 représentent chacun indépendamment un atome d'azote ou C-R3 (G1, G2, G3, G4 et G5 n'étant pas simultanément des atomes d'azote ; et au moins l'un de G1, G2, G3, G4 et G5 étant C-R3), R3 peut être identique ou différent et représente, un atome d'hydrogène, un atome d'halogène, un groupe alkyle en C1-12, un groupe halogénoalkyle en C1-12, un groupe cycloalkyle en C3-8, un groupe alcoxy en C1-6, un groupe alcényloxy en C3-6, un groupe alcynyloxy en C3-6, un groupe halogénoalcoxy en C1-6, un groupe halogénoalcényloxy en C3-6, un groupe halogénoalcynyloxy en C3-6, un groupe alkylthio en C1-6, un groupe alkylsulfinyle en C1-6, un groupe alkylsulfonyle en C1-6, un groupe halogénoalkylthio en C1-6, un groupe halogénoalkylsulfinyle en C1-6, un groupe halogénoalkylsulfonyle en C1-6, un groupe nitro, un groupe cyano, SF5, un groupe phényle éventuellement substitué par 1 à 4 de R4, ou un groupe phénoxy éventuellement substitué par 1 à 4 de R5 ; ou deux R3 forment un cycle comprenant G1 à G5, et si les deux R3 sont respectivement liés à deux atomes de carbone adjacents, les deux R3 peuvent être liés l'un à l'autre, et peuvent en outre former un cycle de 5 ou 6 chaînons saturé ou insaturé conjointement avec les atomes de carbone constitutifs du cycle ; R4 et R5 représentent chacun indépendamment un atome d'halogène, un groupe alkyle en C1-6, un groupe halogénoalkyle en C1-6, un groupe cycloalkyle en C3-8, un groupe alcoxy en C1-6, un groupe halogénoalcoxy en C1-6, un groupe alkylthio en C1-6, un groupe alkylsulfinyle en C1-6, un groupe alkylsulfonyle en C1-4, un groupe halogénoalkylthio en C1-6, un groupe halogénoalkylsulfinyle en C1-6 ou un groupe halogénoalkylsulfonyle en C1-6 ; X, qui peut être identique ou différent, représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle en C1-6, un groupe halogénoalkyle en C1-6, un groupe cycloalkyle en C3-8, un groupe alcoxy en C1-6, un groupe nitro ou un groupe cyano ; n représente un nombre entier de 0 à 2 et m représente un nombre entier de 0 à 3], un N-oxyde de celui-ci ou un sel de celui-ci.
PCT/JP2016/061708 2015-04-28 2016-04-11 Nouveau dérivé 4-pyridinecarboxamide et agents agricoles et horticoles le contenant comme principe actif WO2016175017A1 (fr)

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WO2018199175A1 (fr) * 2017-04-27 2018-11-01 石原産業株式会社 Composé n-(4-pyridyl) nicotinamide ou sel de celui-ci
WO2020254530A1 (fr) 2019-06-18 2020-12-24 Syngenta Crop Protection Ag Dérivés de 7-sulfonyl-n-(1,3,4-thiadiazol-2-yl)-quinoxaline-6-carboxamide et dérivés respectifs de -benzimidazole-5-, -imidazo[4,5-b]pyridine-5-, -3h-furo[3,2b]pyridine-5-, -quinoléine-2- et -naphtalène-2-carboxamide utilisés en tant que pesticides
RU2785399C2 (ru) * 2017-04-27 2022-12-07 Исихара Сангио Кайся, Лтд. Соединение n-(4-пиридил)никотинамид или его соль

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