WO2016068301A1 - Agent de lutte contre les parasites - Google Patents

Agent de lutte contre les parasites Download PDF

Info

Publication number
WO2016068301A1
WO2016068301A1 PCT/JP2015/080774 JP2015080774W WO2016068301A1 WO 2016068301 A1 WO2016068301 A1 WO 2016068301A1 JP 2015080774 W JP2015080774 W JP 2015080774W WO 2016068301 A1 WO2016068301 A1 WO 2016068301A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkylamino
alkenyl
compound
alkynyl
Prior art date
Application number
PCT/JP2015/080774
Other languages
English (en)
Japanese (ja)
Inventor
幸太郎 吉田
直 梅本
達也 可児
Original Assignee
石原産業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 石原産業株式会社 filed Critical 石原産業株式会社
Publication of WO2016068301A1 publication Critical patent/WO2016068301A1/fr

Links

Classifications

    • 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
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached

Definitions

  • the present invention relates to a novel 4- (phenylethenyl) pyridine compound or a salt thereof.
  • Patent Document 1 discloses 3,5-dichloro-4-[(1E) -2- [4- (1,1-dimethylethynyl) phenyl] -1,2-difluoroethenyl] pyridine, 3,5-dichloro It is described that compounds such as -4-[(1E) -2- [4- (1,1-dimethylethynyl) phenyl] -2-fluoroethenyl] pyridine are useful as agricultural and horticultural insecticides. However, compounds having a chloroethenyl moiety are not described.
  • Patent Document 2 describes a phenylethenylpyridine derivative having an insecticidal and acaricidal action and a salt thereof, but does not describe a compound according to the present invention.
  • Non-Patent Document 1 describes (Z) -4- (2-chloro-2-phenylethenyl) pyridine, but this compound is not a compound for agricultural use.
  • the present invention provides a highly active compound against pests, provides a pest control agent using the compound, a method for controlling pests by applying the compound, the compound or a salt thereof
  • An object of the present invention is to provide a production method of the compound and an intermediate for producing the compound.
  • the present inventors have made various studies on pyridine derivatives in order to find better pest control agents. As a result, the present inventors have found that a novel 4- (phenylethenyl) pyridine compound has a very high control effect against pests at a low dose, and completed the present invention.
  • R 1 is a halogen atom, cyano, nitro, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl] , (C 1 -C 6 ) haloalkyl, (C 1 -C 6 ) alkoxy, (C 2 -C 6 ) alkenyloxy, (C 2 -C 6 ) alkynyloxy, (C 3 -C 6 ) cycloalkoxy, ( C 1 -C 6 ) haloalkoxy, (C 1 -C 6 ) alkylthio, (C 2 -C 6 ) alkenylthio, (C 2 -C 6 ) alkynylthio, (C 3 -C 6 ) cycloalkylthio, (C 1- C 6 ) haloalkylthio,
  • R 1 , R 2 and n are as defined above] or a salt thereof.
  • the pest control agent comprising the compound of the formula (I) or a salt thereof as an active ingredient has a very high control effect against pests at a low dose.
  • halogen atom in the formulas (I) and (II) or the halogen as a substituent examples include each atom of fluorine, chlorine, bromine or iodine.
  • the number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
  • alkyl or alkyl moiety in the formulas (I) and (II) examples include methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, isopentyl, neopentyl, and normal hexyl.
  • linear or branched C 1 -C 6 groups such as neohexyl.
  • tertiary may be written as “tert-”.
  • alkenyl or alkenyl moiety in the formulas (I) and (II) examples include vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, 2 -Methyl-2-propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-hexenyl, 2,3 And straight-chain or branched C 2 -C 6 groups such as -dimethyl-2-butenyl.
  • alkynyl or alkynyl moiety in the formulas (I) and (II) examples include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, Linear or branched C 2 ⁇ such as 2-methyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl C 6 group may be mentioned.
  • Examples of the cycloalkyl or cycloalkyl moiety in the formulas (I) and (II) include C 3 -C 6 groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • the salts of the compounds of the formulas (I) and (II) include any salt that is acceptable in the art, for example, ammonium salts such as dimethylammonium salt and triethylammonium salt; hydrochloric acid Inorganic salts such as salts, perchlorates, sulfates, nitrates; organic acid salts such as acetates, trifluoroacetates, oxalates, p-toluenesulfonates, methanesulfonates, etc. It is done.
  • ammonium salts such as dimethylammonium salt and triethylammonium salt
  • hydrochloric acid Inorganic salts such as salts, perchlorates, sulfates, nitrates
  • organic acid salts such as acetates, trifluoroacetates, oxalates, p-toluenesulfonates, methanesulfonates, etc. It is done
  • isomers such as optical isomers
  • present invention includes both isomers and isomer mixtures.
  • isomers are described as a mixture.
  • the present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field.
  • the chemical structure may be different from that of the general formula (I). However, since those skilled in the art can sufficiently recognize that they are related to isomers, Obviously, it is within range.
  • the compound of the above formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following production methods and ordinary salt production methods, but is not limited to these methods. Absent.
  • the compound of the present invention can be produced by reacting the compound of formula (II) or a salt thereof with a chlorinating agent in the presence of a base.
  • This reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; N, N-disubstituted anilines such as dimethylaniline and diethylaniline; 1 type (s) or 2 or more types can be selected and mixed appropriately from the above.
  • the reaction temperature is usually 0 ° C. to 180 ° C., preferably 20 ° C. to 120 ° C.
  • the reaction time is usually several minutes to 24 hours.
  • chlorinating agent examples include thionyl chloride, phosphorus pentachloride, phosphorus oxychloride, phosphorus trichloride and the like.
  • the chlorinating agent is used in an amount of usually 1 mol or more, preferably 1 to 3 mol per mol of the compound of formula (II).
  • the base examples include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydride, potassium hydride and lithium hydride. Alkoxides such as sodium methoxide and sodium ethoxide; tertiary amines such as triethylamine, pyridine and diisopropylethylamine, etc., and tertiary amines are used. Is preferred.
  • the base is used in an amount of usually 1 mol or more, preferably 1 to 3 mol per mol of the compound of formula (II).
  • R 1 and n are as defined above, R 3 is (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, and m is 1 or 2]
  • Examples of the oxidizing agent include peroxides of carboxylic acids such as 3-chloroperbenzoic acid; hydrogen peroxide water.
  • Examples of the solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform.
  • the reaction temperature can usually be in the range of about ⁇ 20 ° C. to the boiling point of the solvent used.
  • the reaction time is usually several minutes to 24 hours.
  • the compound of formula (Id) in which R 2 is (C 2 -C 6 ) alkynyl is obtained by combining the compound of formula (Ic) with (C 2 -C 6 ) alkyne. It can also be produced by reacting in the presence of a palladium catalyst, a copper salt and a base.
  • R 1 and n are as defined above, X is a halogen atom, and R 2a is (C 2 -C 6 ) alkynyl]
  • Examples of the palladium catalyst include bistriphenyltriphenylphosphine palladium dichloride, tetrakis (triphenylphosphine) palladium (0), bis (dibenzylideneacetone) palladium (0), tris (dibenzylideneacetone) dipalladium (0), and the like. Is mentioned.
  • Examples of the copper salt include copper (I) iodide.
  • the base may be an organic base or an inorganic base.
  • the organic base include amine bases such as triethylamine and diisopropylamine.
  • the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • the solvent may be any solvent as long as it is inert to the reaction.
  • an amine base such as triethylamine or diisopropylamine
  • an aprotic polar solvent such as N, N-dimethylformamide or acetonitrile
  • 1 type or 2 types or more can be suitably selected from such ethers.
  • the reaction temperature can usually be about 20 ° C. to a temperature at which the reaction mixture is refluxed.
  • the reaction time is usually several minutes to 24 hours.
  • the compound of the above formula (II) can be produced by reacting the compound of the formula (III) with the compound of the formula (IV) in the presence of a base.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • a solvent any solvent may be used as long as it is inert to the reaction.
  • ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, and 1,4-dioxane are appropriately used.
  • the reaction temperature can usually be in the range of about ⁇ 20 ° C. to the boiling point of the solvent used.
  • the reaction time can usually be from several minutes to 48 hours.
  • Examples of the base include alkali metal amides such as lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, and lithium di (isopropyl) amide.
  • alkali metal amides such as lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, potassium bis (trimethylsilyl) amide, and lithium di (isopropyl) amide.
  • R 4 is (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl or (C 1 -C 6 ) haloalkyl]
  • the reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction.
  • a solvent such as acetonitrile and dioxane; water; can do.
  • the reaction temperature can be generally in the range of about room temperature to the temperature at which the reaction mixture is refluxed.
  • the reaction time can usually be from several minutes to 48 hours.
  • Examples of the acid include inorganic acids such as hydrochloric acid and sulfuric acid; and organic acids such as methanesulfonic acid.
  • Examples of the nitrite include isopropyl nitrite and tert-butyl nitrite.
  • Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkoxides such as sodium methoxide and sodium ethoxide And the like.
  • the compound of the formula (III-b) in which R 2 is SR 4 is a diazonium compound obtained by reacting 3-amino-4-methylpyridine with an inorganic nitrite or nitrite. Thereafter, it can be produced by a Sandmeyer reaction in which R 4 SH or (R 4 S) 2 is reacted.
  • inorganic nitrites include sodium nitrite and potassium nitrite.
  • examples of the nitrite include tert-butyl nitrite and isoamyl nitrite.
  • the reaction can be carried out in the presence of a copper catalyst as necessary.
  • a copper catalyst examples include copper (I) oxide and copper (II) sulfate pentahydrate.
  • the reaction can be performed in the presence of an acid, if necessary.
  • the acid include inorganic acids such as hydrochloric acid and sulfuric acid; organic acids such as acetic acid and methanesulfonic acid; and the like.
  • the reaction can be performed in the presence of a base as necessary.
  • a base examples include alkali metal hydrides such as sodium hydride; alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal water such as lithium hydroxide, sodium hydroxide and potassium hydroxide. Oxides; and the like.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • a solvent include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as toluene and xylene; aprotic polarities such as acetonitrile, N, N-dimethylformamide and dimethyl sulfoxide.
  • One type or two or more types can be appropriately selected from a solvent, water, and the like.
  • the reaction temperature can usually be in the range of ⁇ 20 ° C. to 200 ° C.
  • the reaction time is usually several minutes to 24 hours.
  • Examples of inorganic nitrites and nitrites include those similar to the intermediate production method [3].
  • the halogenating agent include halogens such as chlorine, bromine and iodine; hydrohalic acids such as hydrochloric acid, hydrobromic acid and hydroiodic acid; copper (I) chloride, copper (I) bromide and iodide Examples thereof include copper (I) halides such as copper (I); copper (II) halides such as copper (II) chloride and copper (II) bromide; tetrafluoroboric acid; potassium iodide;
  • the reaction can be carried out in the presence of a copper catalyst as necessary.
  • a copper catalyst include the aforementioned copper (I) halide, copper (II) halide, copper (I) oxide, copper (II) sulfate pentahydrate and the like.
  • the reaction can be performed in the presence of an acid, if necessary.
  • the acid include inorganic acids such as the above-mentioned hydrohalic acids and sulfuric acids; organic acids such as acetic acid, methanesulfonic acid, and p-toluenesulfonic acid.
  • the reaction can be performed in the presence of a solvent, if necessary.
  • a solvent include those similar to the intermediate production method [3], and one or more of these can be appropriately selected and mixed for use.
  • the reaction temperature can usually be in the range of ⁇ 20 ° C. to 200 ° C.
  • the reaction time is usually several minutes to 24 hours.
  • the pest control agent containing the compound of the present invention includes, for example, pests, mites, nematodes or soil pests that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural insecticides, among them insecticides, acaricides, It is useful as a nematode or soil killing pest. It is also useful as an animal parasite control agent, that is, an animal killing parasite agent.
  • the compounds of the present invention are useful as insecticides, acaricides, nematicides or soil pesticides.
  • aphids such as peach aphids, cotton aphids, etc .
  • Agricultural pests such as tree flies, scarab beetles, tamanayaga, kaburayaga, ants, etc .
  • gastropods such as slugs, maimai, etc .
  • sanitary pests such as house dust mites, cockroaches, house flies, mosquitoes, etc .
  • Pests of cereals; clothing such as moths, swordworms, termites, etc., pests such as house pests; Mites; indoor dust mites such as Scarlet mite, Scarlet mite, southern ticks, etc .; such as mites, root-knot nematodes, cyst nematodes, nestle nematodes, rice nesting nematodes, strawberry nematodes, pine wood nematodes, etc. It is effective for the control of soil pests such as nematodes such as plant parasitic nematodes;
  • the insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, it is very useful as an insecticide or acaricide because it shows a further excellent effect in controlling plant parasitic mites and agricultural pests.
  • insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is an organic phosphorus agent, carbamate agent, synthetic pyrethroid agent, neonicotinoid agent and other various resistant insect pests. It is also effective for control.
  • the compound of the present invention has an excellent osmotic transfer property, it can be harmful to soil by treating the soil with an insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention. At the same time as controlling insects, mites, nematodes, gastropods, isopodaes, it is possible to control pests on the foliage.
  • insecticide acaricide, nematicide or soil insecticide containing the compound of the present invention
  • the aforementioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods Insecticides, acaricides, nematicides or soil pesticides that comprehensively control soil pests and the like.
  • Insecticides, acaricides, nematicides or soil pesticides containing the compound of the present invention are usually powders, granules, granule wettable powders by mixing the compound with various agricultural adjuvants, It can be used in various forms such as wettable powder, aqueous suspension, oil suspension, granular aqueous solvent, aqueous solvent, emulsion, liquid, paste, aerosol, microdispersant, etc. As long as it fits the purpose of the present invention, it can be in any formulation form commonly used in the art.
  • adjuvants used in the preparation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, and starch.
  • solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, and starch.
  • a bulking agent for example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction.
  • Various commonly used adjuvants such as agents and antifungal agents can also be used.
  • the blending ratio (weight ratio) of the compound of the present invention and various adjuvants is generally 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10.
  • the application of the insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention is generally based on differences in weather conditions, formulation form, application time, place of application, type of pests and occurrence, etc. Although it cannot be defined, it is generally carried out at an active ingredient concentration of 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm.
  • the application amount per unit area is generally 0.05 to 800 ppm of the compound of the present invention per hectare. 50,000 g, preferably 1 to 30,000 g.
  • the present invention includes a method for controlling pests by such an application method, for example, a method for controlling pests, mites, nematodes or soil pests, particularly plant parasitic mites, agricultural pests, plant parasitic lines. Insect control methods are also included.
  • insecticide, acaricide, nematicide or soil insecticide containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. May show excellent effects and functionality.
  • pesticides include, for example, herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. Is mentioned.
  • the product can improve the application range, the timing of chemical treatment, the control activity, and the like in a preferable direction.
  • the compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be used separately by mixing them at the time of spraying or by using both together.
  • the present invention includes such an insecticidal composition, an acaricidal composition, a nematicidal composition or a soil-killing insect pest composition.
  • Bacillus ⁇ ⁇ ⁇ thuringiensis aizawai Bacillus ⁇ ⁇ ⁇ thuringiensis kurstaki, Bacillus ⁇ thuringiensis israelensis, Bacillus thuringiensis israelensis, Microbial pesticides such as crystal protein toxins, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents, etc.
  • Bacillus thuringiensis such as Gensis Tenebrionis (Bacillus thuringiensis tenebrionis), Avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin (Ivermectin), lepimectin, DE-175, antibiotics and semi-synthetic antibiotics such as abamectin, emamectin, spinetoram; azadirachtin, rotenone Such natural products; repellents such as deet; etc. can also be mixed and used together.
  • an active ingredient compound for example, mepanipyrim, pyrimethanil, cyprodinil ), Anilinopyrimidine compounds such as ferimzone; Tria such as 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole,
  • pesticides that can be used in combination with or combined with the compounds of the present invention include, for example, active compound compounds of herbicides, particularly those of soil treatment type, as described in The Pesticide Manual (15th edition), etc. There is.
  • the animal-killing parasite agent include harmful ectoparasites parasitic on the body surface of the host animal (eg, back, armpit, lower abdomen, inner thigh, etc.)
  • harmful ectoparasites parasitic on the body surface of the host animal eg, back, armpit, lower abdomen, inner thigh, etc.
  • it is effective for controlling harmful endoparasites parasitic on the stomach, intestinal tract, lungs, heart, liver, blood vessels, subcutaneous, lymphatic tissue, etc., and is particularly effective for controlling ectoparasites.
  • ectoparasites examples include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.
  • animal parasitic ticks include Boophilus microplus, Rhipicephalus sanguineus, Scarlet ticks (Haemaphysalis longicornis), Tick ticks (Haemaphysalis flava), Tick ticks (Haemaphysalis campuls , Mites (Haemaphysalis japonica), mites (Haemaphysalis kitaokai), mites (Haemaphysalis ias), mites (Ixodes ovatus), mites (Ixodes nipponensis), mites (Ixodes nipponensis), mushroom mites (Ixodes nipponensis), mites Ticks such as Haemaphysalis megaspinosa), Dermacentor reticulatus, Dermacentor taiwanesis; Dermanyssus gallinae; Ornithonyssus
  • animal parasitic fleas include ectoparasite worms belonging to the order Flea (Siphonaptera), and more specifically fleas belonging to the family Flea (Pulicidae), Cleaphyllus (Ceratephyllus), and the like.
  • 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 mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus);
  • the animalicidal parasite agent containing the compound of the present invention is effective for controlling fleas belonging to the family flea family, especially dog fleas, cat fleas and the like.
  • ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as cat lice; blood-sucking dipterous pests such as bovine abs, quail sharks, .
  • endoparasites include nematodes such as lungworm, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms; Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke like liver fluke; coccidium, malaria parasite, intestinal granulocyst, toxoplasma, chestnut Protozoa such as Ptosporidium, and the like.
  • nematodes such as lungworm, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms
  • Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms
  • Japanese schistosomiasis fluke like liver fluke
  • Examples of host animals include various pet animals, livestock, and poultry. More specifically, for example, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, nine-birds, wild birds, parakeets, juvenile pine, canary, etc.) Pigs, sheep, ducks, chickens, etc.
  • the animal killing parasite agent containing the compound of the present invention is effective for controlling pests or ticks that are externally parasitic on pet animals or livestock.
  • pet animals or domestic animals it is particularly effective for dogs, cats, cows or horses.
  • the compound of the present invention when used as an animal killing parasite, it may be used as it is, and together with suitable adjuvants, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aqueous suspensions, It can also be formulated and used in various forms such as an oily suspension.
  • suitable adjuvants powders, granules, tablets, powders, capsules, liquid agents, emulsions, aqueous suspensions
  • suitable adjuvants powders, granules, tablets, powders, capsules, liquid agents, emulsions, aqueous suspensions
  • suitable adjuvants powders, granules, tablets, powders, capsules, liquid agents, emulsions, aqueous suspensions
  • It can also be formulated and used in various forms such as an oily suspension.
  • any preparation forms used in the normal field can be used as long as the object of the present invention is met.
  • anionic surfactants and nonionic surfactants exemplified as auxiliary agents for preparation of the above-mentioned insecticides, acaricides, nematicides or soil insecticides
  • a cationic surfactant such as cetyltrimethylammonium bromide; water, acetone, acetonitrile, N-methylacetamide, N, N-dimethylacetamide, N, N-dimethylformamide, 2-pyrrolidone, N-methyl-2 -Pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, Solvents such as ethylene glycol monoethyl ether, diethylene glycol normal butyl ether, di
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention.
  • it can be used by appropriately selecting from those known in the field, and further, selected from various adjuvants used in the above-mentioned agricultural and horticultural fields. You can also
  • the compounding ratio (weight ratio) of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10.
  • a diluent such as water
  • various spreading agents for example, surfactants, vegetable oils, mineral oils, etc.
  • Administration of the compound of the present invention to the host animal is performed orally or parenterally.
  • the oral administration method include a method of administering tablets, liquid agents, capsules, wafers, biscuits, minced meat, and other feeds containing the compound of the present invention.
  • the compound of the present invention is prepared into an appropriate preparation and taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on ) Treatment, pour-on treatment, spray treatment, and the like; and a method of embedding a resin piece containing the compound of the present invention under the skin of a host animal.
  • the dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptom, etc., but is generally 0.01 mg to 100 g, preferably 0.1 mg to 10 g, per 1 kg body weight of the host animal. It is appropriate to administer in proportions.
  • the present invention also includes a method for controlling animal parasites by the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.
  • the present invention by controlling harmful animal parasites as described above, various host animal diseases caused by them may be prevented or treated.
  • the present invention includes a prophylactic or therapeutic agent for parasitic animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasitic animal diseases.
  • the compound of the present invention When the compound of the present invention is used as an animal killing parasite, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, It can be mixed with or used in combination with preservatives. In addition, if necessary, other animal drugs and agricultural chemicals such as anthelmintics, anticoccidials, insecticides, acaricides, fleas, nematicides, fungicides, antibacterials, etc. In this case, a better effect may be exhibited.
  • the present invention includes a composition for controlling animal parasites in which various components as described above are mixed or used together, and a method for controlling animal parasites using the composition, in particular, control of ectoparasites or endoparasites. A method is also included.
  • R 1 and R 2 are as defined above] or a 4- (phenylethenyl) pyridine compound or a salt thereof.
  • R 1 is a halogen atom, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl or (C 1 -C 6 ) haloalkoxy
  • R 2 is a halogen atom, (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) alkylsulfinyl, (1) or (2) which is (C 1 -C 6 ) alkylsulfonyl, (C 1 -C 6 alkoxy) carbonyl, (C 1 -C 6 alkyl) aminocarbonyl or di (C 1 -C 6 alkyl) aminocarbonyl 4- (phenylethenyl) pyridine-based compound or a salt thereof according to (4).
  • R 1 is a halogen atom, (C 1 -C 6 ) alkyl or (C 1 -C 6 ) haloalkoxy.
  • R 2 is a halogen atom, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) alkylsulfinyl or (C 1-
  • R 1 and R 2 are as defined above] or a salt thereof.
  • R 1 is a halogen atom, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) haloalkyl or (C 1 -C 6 ) haloalkoxy
  • R 2 is a halogen atom, (C 1 -C (1) or (2) which is 6 ) alkyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkylthio, (C 1 -C 6 ) alkylsulfinyl or (C 1 -C 6 ) alkylsulfonyl Or a salt thereof.
  • the reaction solution was neutralized with a saturated aqueous sodium hydrogen carbonate solution, and then a saturated aqueous sodium thiosulfate solution (200 mL) was added.
  • the reaction mixture was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. After anhydrous sodium sulfate was removed by filtration, the solvent was distilled off under reduced pressure.
  • Test Example 2 Effect Test on Tobacco Whitefly To a pot-planted cucumber seedling parasitized with 1 to 2 instar larvae, a chemical solution prepared to a concentration of 200 ppm of the compound of the present invention was sprayed using a hand spray. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Ten days after the treatment, the number of old larvae was examined, and the control value was determined by the following formula. As a result, the compound no. I-41, I-64, I-122, I-123, I-124, I-125, I-126, I-127, I-128 and II-41 showed control values of 90 or more.
  • Control value [1 ⁇ (Ta ⁇ Cb) / (Tb ⁇ Ca)] ⁇ 100
  • Ta Number of old larvae after treatment in treated cucumber seedling
  • Tb Number of first to second larvae before treatment in treated cucumber seedling
  • Ca Number of old larvae after treatment in untreated cucumber seedling
  • Cb Before treatment in untreated cucumber seedling Number of larvae 1-2
  • Formulation Example 1 (1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalene sulfonate 2 parts by weight or more To make a wettable powder.
  • Formulation Example 2 (1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.
  • Formulation Example 3 (1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 4 (1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the present compound Mix at a weight ratio of 4: 1 to make a wettable powder.
  • Formulation Example 5 (1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.
  • Formulation Example 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1 ) To (3) are mixed uniformly in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.
  • Formulation Example 7 (1) Compound of the present invention 2.5 parts by weight (2) N, N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to give a trace amount of spray ( ultra low volume formulation).
  • Formulation Example 8 (1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain a liquid agent.

Landscapes

  • 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)

Abstract

　L'objet de la présente invention est de fournir un composé hautement actif contre les parasites. La présente invention concerne des composés 4-(phényléthényl)pyridine représentés par la formule (I) et leurs sels. (Dans la formule : R1 représente un atome d'halogène, un alkyle en (C1-C6), un halogénoalkyle en (C1-C6), un halogénoalcoxy en (C1-C6), etc.; R2 représente un atome d'halogène, un alkyle en (C1-C6), un alcoxy en (C1-C6), un alkylthio en (C1-C6), un alkylsulfinyle en (C1-C6), un alkylsulfonyle en (C1-C6), un (alcoxy en C1-C6)carbonyle, un (alkyle en C1-C6)aminocarbonyle, un di(alkyle en C1-C6)aminocarbonyle, etc.; n représente un nombre entier de 0 à 5, et lorsque n est supérieur ou égal à 2, de multiples motifs R1 peuvent être identiques ou différents).
PCT/JP2015/080774 2014-10-31 2015-10-30 Agent de lutte contre les parasites WO2016068301A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014222136A JP2017222576A (ja) 2014-10-31 2014-10-31 有害生物防除剤
JP2014-222136 2014-10-31

Publications (1)

Publication Number Publication Date
WO2016068301A1 true WO2016068301A1 (fr) 2016-05-06

Family

ID=55857634

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2015/080774 WO2016068301A1 (fr) 2014-10-31 2015-10-30 Agent de lutte contre les parasites

Country Status (2)

Country Link
JP (1) JP2017222576A (fr)
WO (1) WO2016068301A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017159618A1 (fr) * 2016-03-18 2017-09-21 石原産業株式会社 Agent de lutte contre les animaux nuisibles
JP2019531299A (ja) * 2016-09-30 2019-10-31 オシェラ インコーポレイテッドＯｚｃｈｅｌａ Ｉｎｃ． スチルベン誘導体及びその製造方法
JPWO2018169045A1 (ja) * 2017-03-17 2020-01-16 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 中気門亜目ダニ類の防除剤

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2427286A (en) * 1943-04-28 1947-09-09 Gen Chemical Corp Insecticide and method of using
US2512180A (en) * 1947-01-31 1950-06-20 American Cyanamid Co 1-(p-chlorophenyl)-2-pyridylacetylenes and 1-(p-chlorophenyl)-2-quinolylacetylenes
JPH01316359A (ja) * 1988-03-23 1989-12-21 Idemitsu Kosan Co Ltd ピリジン誘導体および該誘導体を有効成分とする殺虫・殺ダニ剤
JPH02306964A (ja) * 1989-05-19 1990-12-20 Idemitsu Kosan Co Ltd ピリジン誘導体および該誘導体を有効成分とする殺虫・殺ダニ剤
WO1994002465A1 (fr) * 1992-07-28 1994-02-03 Rhone-Poulenc Rorer Limited Inhibiteurs de phosphodiesterase d'amp cyclique et du facteur de necrose tumorale
US5837719A (en) * 1995-08-10 1998-11-17 Merck & Co., Inc. 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use
US20020115669A1 (en) * 2000-08-31 2002-08-22 Wiedeman Paul E. Oxazolidinone chemotherapeutic agents
WO2006113704A2 (fr) * 2005-04-18 2006-10-26 Neurogen Corporation Antagonistes cb1 heteroaryle substitue
WO2012085721A1 (fr) * 2010-12-20 2012-06-28 Pfizer Inc. Nouveaux composés fusionnés de pyridine en tant qu'inhibiteurs de la caséine kinase
WO2013158422A1 (fr) * 2012-04-17 2013-10-24 E. I. Du Pont De Nemours And Company Composés hétérocycliques pour la lutte contre des animaux nuisibles invertébrés

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2427286A (en) * 1943-04-28 1947-09-09 Gen Chemical Corp Insecticide and method of using
US2512180A (en) * 1947-01-31 1950-06-20 American Cyanamid Co 1-(p-chlorophenyl)-2-pyridylacetylenes and 1-(p-chlorophenyl)-2-quinolylacetylenes
JPH01316359A (ja) * 1988-03-23 1989-12-21 Idemitsu Kosan Co Ltd ピリジン誘導体および該誘導体を有効成分とする殺虫・殺ダニ剤
JPH02306964A (ja) * 1989-05-19 1990-12-20 Idemitsu Kosan Co Ltd ピリジン誘導体および該誘導体を有効成分とする殺虫・殺ダニ剤
WO1994002465A1 (fr) * 1992-07-28 1994-02-03 Rhone-Poulenc Rorer Limited Inhibiteurs de phosphodiesterase d'amp cyclique et du facteur de necrose tumorale
US5837719A (en) * 1995-08-10 1998-11-17 Merck & Co., Inc. 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use
US20020115669A1 (en) * 2000-08-31 2002-08-22 Wiedeman Paul E. Oxazolidinone chemotherapeutic agents
WO2006113704A2 (fr) * 2005-04-18 2006-10-26 Neurogen Corporation Antagonistes cb1 heteroaryle substitue
WO2012085721A1 (fr) * 2010-12-20 2012-06-28 Pfizer Inc. Nouveaux composés fusionnés de pyridine en tant qu'inhibiteurs de la caséine kinase
WO2013158422A1 (fr) * 2012-04-17 2013-10-24 E. I. Du Pont De Nemours And Company Composés hétérocycliques pour la lutte contre des animaux nuisibles invertébrés

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
CHEN, C-Y. ET AL., J.ORG.CHEM., vol. 70, 2005, pages 6964 - 6967 *
COMINS,D.L. ET AL., TETRAHEDRON LETTERS, vol. 25, no. 31, 1984, pages 3297 - 3300 *
DATABASE REGISTRY 2 December 2013 (2013-12-02), retrieved from STN Database accession no. 1485354-05-9 *
DATABASE REGISTRY 28 October 2013 (2013-10-28), retrieved from STN Database accession no. 1465180-81-7 *
DATABASE REGISTRY 4 December 2013 (2013-12-04), retrieved from STN Database accession no. 1486679-95-1 *
DATABASE REGISTRY 9 December 2013 (2013-12-09), retrieved from STN Database accession no. 1490728-96-5 *
NISHIKAWA,S. ET AL., J.AGRIC.FOOD CHEM., vol. 44, 1996, pages 1337 - 1342 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017159618A1 (fr) * 2016-03-18 2017-09-21 石原産業株式会社 Agent de lutte contre les animaux nuisibles
JP2019531299A (ja) * 2016-09-30 2019-10-31 オシェラ インコーポレイテッドＯｚｃｈｅｌａ Ｉｎｃ． スチルベン誘導体及びその製造方法
JPWO2018169045A1 (ja) * 2017-03-17 2020-01-16 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 中気門亜目ダニ類の防除剤
JP7090071B2 (ja) 2017-03-17 2022-06-23 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 中気門亜目ダニ類の防除剤
US12108761B2 (en) 2017-03-17 2024-10-08 Meiji Seika Pharma Co., Ltd. Mesostigmata mite control agent

Also Published As

Publication number Publication date
JP2017222576A (ja) 2017-12-21

Similar Documents

Publication Publication Date Title
JP2013028588A (ja) 有害生物防除剤
JP5231829B2 (ja) ピリジル−トリアゾロピリミジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法
WO2010018868A1 (fr) Agent antiparasitaire contenant un dérivé triazolopyrimidine ou un sel de celui-ci
JP2012087116A (ja) ベンズアミド誘導体又はその塩、それらを含有する殺虫剤、殺ダニ剤、殺線虫剤又は殺土壌害虫剤
JP2010138166A (ja) 新規ピリジン誘導体又はその塩、それらを含有する有害生物防除剤並びにそれらの製造方法
WO2018199175A1 (fr) Composé n-(4-pyridyl) nicotinamide ou sel de celui-ci
JP2011168582A (ja) トリアゾロピリジン誘導体又はその塩、それらの製造方法及びそれらを含有する有害生物防除剤
JP2011144169A (ja) イミダゾピリミジン誘導体又はその塩、並びにそれらを含有する有害生物防除剤
WO2016068301A1 (fr) Agent de lutte contre les parasites
WO2017222037A1 (fr) Composé de n-(4-pyridyl) benzamide ou son sel, et agent antiparasitaire contenant ledit composé ou son sel en tant qu'ingrédient actif
JP2011105700A (ja) ジアリールトリアゾール誘導体又はその塩、それらを含有する殺虫剤、殺ダニ剤、殺線虫剤又は殺土壌害虫剤、並びにそれらの製造方法
JP2016020335A (ja) 有害生物防除剤
JP2016050201A (ja) 有害生物防除剤
JP2010195771A (ja) トリアゾロピリミジン誘導体又はその塩、それらの製造方法及びそれらを含有する有害生物防除剤
JP2016204325A (ja) 有害生物防除剤
JP6303250B2 (ja) 有害生物防除剤
WO2017159618A1 (fr) Agent de lutte contre les animaux nuisibles
JP2018145187A (ja) 置換ピリジン系化合物又はその塩を有効成分として含有する有害生物防除剤
JP2017008029A (ja) Ｎ−（４−ピリジル）ピコリンアミド化合物又はその塩を有効成分として含有する有害生物防除剤
WO2010018853A1 (fr) Dérivé pyridyle-triazolopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nocifs le comprenant
WO2017200100A1 (fr) Composé de n-(4-pyridyl) benzamide ou son sel, et agent antiparasitaire contenant ledit composé ou son sel en tant qu'ingrédient actif
JP2008019222A (ja) アントラニルアミド系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
JP2006131608A (ja) アントラニルアミド系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
JP2016014016A (ja) 有害生物防除剤
WO2019163921A1 (fr) Composé de pyridine substitué et sel de celui-ci

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 15854328

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: JP

122 Ep: pct application non-entry in european phase

Ref document number: 15854328

Country of ref document: EP

Kind code of ref document: A1