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WO2006080311A1 - Composé de type anthranilamide, méthode de synthèse dudit composé et agent pesticide contenant ledit composé - Google Patents

Composé de type anthranilamide, méthode de synthèse dudit composé et agent pesticide contenant ledit composé Download PDF

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Publication number
WO2006080311A1
WO2006080311A1 PCT/JP2006/301057 JP2006301057W WO2006080311A1 WO 2006080311 A1 WO2006080311 A1 WO 2006080311A1 JP 2006301057 W JP2006301057 W JP 2006301057W WO 2006080311 A1 WO2006080311 A1 WO 2006080311A1
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Prior art keywords
alkyl
compound
optionally substituted
formula
amino
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PCT/JP2006/301057
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English (en)
Japanese (ja)
Inventor
Toru Koyanagi
Tetsuo Yokeda
Koji Higuchi
Kazuhisa Kiriyama
Yohei Taguchi
Taku Hamamoto
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Ishihara Sangyo Kaisha, Ltd.
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Publication of WO2006080311A1 publication Critical patent/WO2006080311A1/fr

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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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/18—One oxygen or sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/38—Nitrogen atoms

Definitions

  • WO01Z70671 discloses anthranilamide compounds having a certain chemical structure. However, as a substituent corresponding to A in the following formula (I), C
  • WO04Z67528 discloses compounds in which pyridyl is substituted at the 1-position of the pyrazole ring.
  • a phenol is substituted at the 1-position of the pyrazole ring of the formula (I) described later, and the chemical structures of the two are different.
  • Patent Document 1 International Publication WO01Z70671
  • Patent Document 2 International Publication WO04Z67528
  • a number of pest control agents have been used for many years, but many have various problems such as insufficient efficacy, pests gaining resistance and limiting their use. Therefore, it is desired to develop a new pest control agent with few disadvantages, for example, a pest control agent capable of controlling various pests that are problematic in the field of agriculture and horticulture, and pests parasitic on animals.
  • the present inventors have made various studies on anthranilamide compounds in order to find better pest control agents. As a result, the present inventors have found that a novel anthra-amide compound has an extremely high control effect against pests at a low dose, and completed the present invention. That is, the present invention provides a compound of formula (I):
  • R 1 is halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, trialkylsilylethynyl, hydroxy, alkoxy, haloanoloxy, honoleminore, anorequinole Canoleboninole, haloanorequinolecanoleboninole, force noreboxinole, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano, nitro, amino, alkylamino, dialkylamino, even substituted A good phenoxy, an optionally substituted pyridyloxy, an optionally substituted phenoxycarbon or an optionally substituted pyridyloxycarbon, and R 2 is a hydrogen atom, halogen, alkyl, haloalkyl, alkenyl
  • the present invention provides an anthracamide compound or a salt thereof, a production method thereof, a pest control agent containing them, and the like.
  • R 1 is halogen, alkyl, haloalkyl, alkyl, trialkylsilylether, hydroxy, formyl, carboxyl, alkoxycarbole, aminocarbol, alkylaminocarbol
  • R 2 is a hydrogen atom, halogen, haloalkyl, haloalkoxy or alkylsulfoxy
  • R 3 is halogen, alkyl, haloalkyl, alkoxy or -tro
  • A is substituted with Y Y is C cycloalkyl optionally substituted with at least one substituent selected from the group consisting of halogen, alkyl and haloalkyl
  • m is 0-4
  • w is 0 to 5, or a salt thereof.
  • R 2 is a hydrogen atom, halogen, haloalkyl or haloalkoxy
  • R 3 is a norogen, alkyl, haloalkyl or -tro.
  • R is a hydrogen atom, halogen, alkyl, haloalkyl, alkyl, haloalkenyl, alkyl, haloalkynyl, hydroxy, alkoxy, nitro-containing amino
  • R 12 and R 14 are R 13 is a hydrogen atom
  • R 13 is a hydrogen atom, halogen, alkyl, haloalkyl, alkyl, trialkylsilyl ether, hydroxy, alkoxy, haloalkoxy, formyl, alkylcarbole, haloalkylcarbole, carboxyl, alkyl Coxoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbol, cyano-substituted nitro, ami-substituted alkylamino, dialkyla-substituted phenoxy, optionally substituted pyridyloxy, substitutedObviously, phenoxy
  • R 11 is a hydrogen atom, halogen, alkyl, hydroxy, nitro or amino
  • R 12 and R 14 are hydrogen atoms
  • R 13 is a hydrogen atom, halogen, alkyl, haloalkyl, alkyl, trialkyl Silylethynyl, hydroxy, formyl, carboxyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbol, cyano or -tro
  • R 2 is a hydrogen atom, halogen, haloalkyl, haloalkoxy or alkylsulfoxy.
  • R 31 is a hydrogen atom, halogen, alkyl, haloalkyl, alkoxy or -tro
  • R 32 and R 34 are hydrogen atoms
  • R 33 is a hydrogen atom or halogen
  • R 35 is a hydrogen atom, halogen or Alkyl
  • A is alkyl substituted with C cycloalkyl
  • R 11 is halogen or alkyl
  • R 12 and R 14 are hydrogen atoms
  • R 13 is a hydrogen atom, halogen, alkyl, haloalkyl, alkyl, carboxyl, alkoxycarbonyl, aminocarbonyl
  • R 2 is a hydrogen atom, halogen or haloalkyl
  • R 31 is a hydrogen atom, halogen, alkyl, haloalkyl or -tro
  • R 32 and R 34 are hydrogen atoms.
  • R 33 is a hydrogen atom or a halogen
  • R 35 is a hydrogen atom, halogen or alkyl, or the compound or salt thereof according to (3) above.
  • the pest control agent comprising the novel anthranilamido compound of formula (I) as an active ingredient has a very high control effect against pests at a low dose.
  • substituents of phenoxycarbol or substituted pyridyloxycarbol include, for example, halogen, alkyl, haloalkyl, hydroxy, alkoxy, haloanalkoxy, anolequinoles norephenol, no, loa Norequinoles Norefuenore, Anolequinores Norefininore, Noroanorequinores Nolefininore, Anolequinores Norehoninore, No, Roanorequinoles Norehoninore, Ciano, Nitro, Ami Alkylamino And dialkylamino.
  • the number of substitutions of these substituents is 1 or 2 or more, and when it is 2 or more, each substituent may be the same or different.
  • the position of each substituent may be any position.
  • the number of substitutions of substituent Y in A is 1 or 2 or more, and when it is 2 or more, each substituent Y may be the same or different. Further, the substitution position of the substituent Y may be any position.
  • the number of substituents Y in A is preferably 1.
  • alkyl or haloalkyl which is a substituent of C cycloalkyl in Y
  • the number of substitutions is 1 or 2 or more. When the number is 2 or more, each substituent may be the same or different. In addition, the substitution position of each substituent may be a shift position.
  • Alkyl is preferably unsubstituted or has 1 to 5 substituents when it has the above-mentioned substituents.
  • halogen in R 2 , R 3 or Y or the halogen as a substituent examples include each atom of fluorine, chlorine, bromine or iodine.
  • the number of halogens as substituents is 1 or 2 or more. When 2 or more, each halogen may be the same or different. Also, the position of halogen substitution may be the position of displacement.
  • the alkyl or alkyl moiety in R ⁇ R 2 , R 3 , A or Y may be linear or branched! /, Specific examples of which are methyl, ethyl, propyl, isopropyl, butyl, Examples include C-types such as tertiary butinore, pentinore, and hexinore.
  • alkenyl or alkenyl moiety in R 1 may be linear or branched.
  • alkellyl or alkenyl moiety include bulle, 1-probe, allyl, iso-probe, 1-tuttle, 1, 3—Butageninore, 1 C such as Hexeninore.
  • the alkyl or alkyl moiety in R 1 may be linear or branched, and specific examples thereof include ethur, 2-butul, 2-pentyl, and 3-hexynyl. And so on.
  • Specific examples of c cycloalkyl or cycloalkyl moiety in Y include cyclopropyl.
  • the salt of the anthracamide compound of the formula (I) includes any one that is agriculturally acceptable, and examples thereof include alkali metal salts such as sodium salt and potassium salt.
  • Alkaline earth metal salts such as magnesium salts and calcium salts; ammonium salts such as dimethyl ammonium salts and triethyl ammonium salts; such as hydrochlorides, perchlorates, sulfates and nitrates; Inorganic acid salts; organic acid salts such as acetate and methanesulfonate.
  • the anthranilamide-based compound of the formula (I) may have different isomers such as optical isomers and geometric isomers. In the present invention, both isomers and isomer mixtures are present. Is included.
  • the present invention includes various isomers other than those described above within the scope of common technical knowledge in the technical field. In addition, depending on the type of isomer, there may be a chemical structure different from that of the above formula (I). However, since those skilled in the art can sufficiently recognize that they are related to isomers, Obviously, it is within range.
  • the anthranilamido compound of the formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following reactions [A] to [0] and a usual salt production method. it can.
  • Reaction [A] can usually be carried out in the presence of a base when Z is a chlorine atom.
  • a base examples include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metals such as sodium hydride and potassium hydride.
  • the base can be used in an amount of 1 to 5 times mol, preferably 1 to 2.5 times mol, of the compound of formula (II).
  • the reaction [ ⁇ ] can be carried out in the presence of a solvent if desired when ⁇ is a chlorine atom.
  • a solvent may be used as long as it is inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane, Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, trichloroethane, and dichloroethylene; aromatic hydrocarbons such as benzene, toluene, and xylene; pentane, hexane, heptane, octane, and cyclohexane Aliphatic hydrocarbons such as: acetonitol, propio-tolyl, ⁇ , ⁇ dimethylformamide, dimethylsulfox
  • the reaction [ ⁇ ] can be carried out usually at 20 to + 60 ° C, preferably 0 to 30 ° C, and the reaction time is usually about 1 to 24 hours, Desirably, the time can be about 2 to 12 hours.
  • reaction [A] is usually carried out in the presence of a dehydration condensing agent and a solvent when Z is —OH.
  • Examples of the dehydrating condensing agent include carbodiimides such as ⁇ , ⁇ ′-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, and 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride.
  • carbodiimides such as ⁇ , ⁇ ′-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, and 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride.
  • the solvent may be any solvent inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene , Dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene, etc .
  • aromatic hydrocarbons such as benzene, toluene, xylene; , Propio-tolyl, ⁇ , ⁇ dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, ⁇ -methylpyrrolidone, polar aprotic solvents; methyl acetate, ethyl acetate, acetic acid Esters such as propyl; ketones such as acetone, jetyl ketone,
  • the reaction [ ⁇ ] can usually be carried out at 20 to + 60 ° C, preferably 0 to 30 ° C, when the moth is ⁇ , and the reaction time is usually about 0.5 to 24 hours. Desirably, it can be about 1 to 12 hours.
  • reaction [A] is usually performed in the presence of a base and a solvent when Z is C alkoxy.
  • Bases include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metals such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide Alkoxides; and trimethylamine, triethylamine, triisopropylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, 2,6 dimethylpyridine, 4 pyrrolidinopyridine, N-methylmorpholine, ⁇ , ⁇ Dimethylaniline, ⁇ , ⁇ Jetylaniline, ⁇ Ethyl ⁇ -Methyl lin, 1,8 Diazabicyclo [5.4.0] 1-7 Undecene, 1,4-Diazabicyclo [2.2.2] Octanes like tertiary amines From the above, one or more can be selected as appropriate.
  • the base can be used in an amount of 1 to 5 times
  • the solvent may be any solvent that is inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene
  • Halogenated hydrocarbons such as benzene, toluene, xylene; pentane, hexane, heptane, octane, cyclohexane, halogenated hydrocarbons such as dichloromethane, chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene
  • Aliphatic hydrocarbons such as hexane; acetonitrile, propio-tolyl, ⁇ , ⁇ dimethylformamide, dimethyl sulfoxide, hexame
  • Polar aprotic solvents such as til phosphoric triamide, s
  • reaction [A] is usually 0 to 120 ° C, preferably 5 to 80 ° C when Z is C alkoxy.
  • the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours.
  • R 2 , R 3 , A, m and w are as described above.
  • the reaction] can usually be performed in the presence of a solvent.
  • any solvent may be used as long as it is inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane, Halogenated hydrocarbons such as chlorophenol, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene, xylene; pentane, Aliphatic hydrocarbons such as hexane, heptane, octane, cyclohexane; and acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethyla One or two or more kinds of polar aprotic
  • the reaction] can usually be carried out at 0 to 120 ° C, preferably 20 to 80 ° C, and the reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours.
  • R 2a is a hydrogen atom, a fluorine atom, a chlorine atom, an odor atom, an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, a cyanalkoxy, an alkylsulfonyloxy
  • R 3a is a fluorine atom, a chlorine atom, a bromine atom, an alkyl, a haloalkyl, an alkoxy, a haloalkoxy, a cyanalkoxy, an alkylsulfo-loxy, a cyano-containing nitro
  • an amino X is an bromine atom or an iodine atom.
  • Examples of the metal cyanide in the reaction [C] include cyanogen copper, zinc cyanide, cyanide. One type or two or more types can be appropriately selected from potassium fluoride and the like.
  • the metal cyanide can be used in an amount of 1 to 30 times mol, preferably 1 to 15 times mol for the compound of formula (1-1).
  • the reaction] can usually be carried out in the presence of a solvent.
  • a solvent any solvent inert to the reaction may be used.
  • ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl, ⁇ , ⁇ -Dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, ⁇ -methylpyrrolidone and other polar aprotic solvents, etc. I can do it.
  • the reaction [C] can be carried out in the presence of a palladium catalyst, if desired.
  • a palladium catalyst for example, one or more of tetrakistriphenylphosphine palladium and bistriphenylphosphine palladium dichloride can be appropriately selected.
  • the reaction can be carried out in the presence of a metal iodide if desired.
  • the metal iodide one or more kinds can be appropriately selected from, for example, copper iodide, zinc iodide, potassium iodide and the like.
  • the reaction can be carried out usually at 0 to 150 ° C, preferably 10 to: LOO ° C, and the reaction time can be usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. .
  • R 2a , R 3a , A, m, w and X are as described above.
  • Carbon monoxide in the reaction [D] can be used in an amount of 1 to 200 times mol, preferably 1 to 50 times mol, of the compound of the formula (1-1).
  • the hydrogen donor in the reaction [D] one or two or more kinds can be appropriately selected from, for example, tryptyl tin hydride, poly (methylhydrosiloxane), trioctylsilyl hydride and the like.
  • the hydrogen donor can be used in an amount of 1 to 2 moles, preferably 1 to 1.5 moles relative to the compound of the formula (1-1).
  • Reaction [D] can be normally performed in presence of a palladium catalyst.
  • a palladium catalyst for example, one or two or more kinds can be appropriately selected from those mentioned in the above reaction [C].
  • the reaction [D] can be usually performed in the presence of a solvent.
  • a solvent any solvent inert to the reaction may be used.
  • aromatic hydrocarbons such as benzene, toluene, xylene; pentane, hexane, heptane, octane, cyclohexane, etc.
  • Aliphatic hydrocarbons such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethyl sulfoxide, hexamethyl Phosphoric tri
  • polar aprotic solvents such as amide, sulfolane, dimethylacetamide and N-methylpyrrolidone.
  • Reaction [D] is usually 0 to 150 ° C, preferably 10 to: LOO ° C, and the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. Can do.
  • R 2 , RA, m and w are as described above, R la is halogen, alkyl, haloalkyl, anorekeninore, haloanorekeninore, anorequininore, haloanorequininore, trianolenoquinoline reethinyl, Hydroxy, alkoxy, haloalkoxy, alkylcarbonyl, haloalkyl force carbonyl, carboxyl, alkoxycarbonyl, haloalkoxycarbon, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano, nitro, aminoalkylamino, dialkylamino, An optionally substituted phenoxy, optionally substituted, pyridyloxy, optionally substituted, phenoxycarbon or optionally substituted !, pyridyloxycarbonyl.
  • fluorinating agent in the reaction examples include cetylfluoride trifluoride, [bis (2-methoxyethyl) amino] sulfur trifluoride, xenon fluoride, 2,2-difluoro-1,3 dimethylimidazolidine, tetrafluoride.
  • One or more types can be appropriately selected from sulfur fluoride.
  • Fluorine glaze is 1 to 10 moles, preferably 1 to 4 moles relative to the compound of formula (1-4). Double moles can be used.
  • the reaction [E] can usually be carried out in the presence of a solvent.
  • the solvent may be any solvent inert to the reaction.
  • aliphatic hydrocarbons such as pentane, hexane, heptane, octane, isooctane and cyclohexane; benzene, toluene, Aromatic hydrocarbons such as silene; halogenated hydrocarbons such as black benzene, dichlorobenzene, dichloromethane, black mouth form, carbon tetrachloride, chlorotrichloromethane, dichloroethane, trichloroethane, and dichloroethylene.
  • ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane, 2-methoxyethyl ether, and the like can be appropriately selected.
  • the reaction can be carried out in an inert gas atmosphere if desired.
  • the inert gas include nitrogen, helium, and argon.
  • the reaction can be carried out usually at -78 ° C to 40 ° C, preferably at 40 ° C to 25 ° C, and the reaction time is usually about 2 to 24 hours, preferably about 5 to 15 hours.
  • R 1, R 2, A, m, w and X are as described above, Q is alkyl or trialkylsilyl, L is a chlorine atom, bromine atom or iodine atom, and R A is alkyl.
  • the compound of the formula (1-1), the formula (VI-1), the formula (VI-2) ) Or a compound of formula (VI-3) may be reacted in the presence of a palladium catalyst and a base.
  • the compound of formula (VI-1), the compound of formula (VI-2) or the compound of formula (VI-3) is usually 1.0 to 10 equivalents, preferably 1.0 to Used at a rate of 3.0 equivalents.
  • a solvent can be used in some cases. Any solvent can be used as long as it does not inhibit the progress of this reaction, for example, ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane.
  • ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane
  • black benzene dichlorobenzene, dichloromethane.
  • Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylform
  • Polar aprotic solvents such as amide, dimethyl sulfoxide, dimethylacetamide, N-methylpyrrolidone
  • esters such as methyl acetate, ethyl acetate, propyl acetate; acetone, jetyl ketone, methyl ethyl ketone, methyl isobutyl ketone 1 type or 2 types or more can be appropriately selected from ketones such as: amines such as dimethylamine and triethylamine; and water.
  • Examples of the base used in the reaction [F] include inorganic salts such as sodium carbonate and potassium carbonate; propylamine, butylamine, jetylamine, diisopropylamine, triethylamine, tributylamine, diisopropylethylamine, Examples thereof include organic amines such as pyrrolidine and piperidine, and are usually used in a proportion of 1.0 to 30 equivalents, preferably 1.0 to 15.0 equivalents, relative to the compound of formula (1-1).
  • Examples of the palladium catalyst used in the reaction [F] include tetrakistriphenylphosphine palladium, dichlorobis (triphenylphosphine) palladium, palladium acetate-triphenylphosphine, and the like. Used in a ratio of 0.001 to 0.1 equivalents. When using a palladium catalyst, 0.001 to 0.1 equivalent to the compound of formula (1-1) in which tertiary phosphine such as triphenylphosphine and tri-(.- tolyl) phosphine may coexist. Used at a rate of
  • catalysts that may be used include copper halides such as copper (I) iodide, and ammonium salts such as tetraptylammobromide.
  • copper halides such as copper (I) iodide
  • ammonium salts such as tetraptylammobromide.
  • the compound (1-1) is used in a proportion of 0.001 to 0.3 equivalent.
  • the reaction temperature for reaction (F) is usually 0 ° C to 150 ° C, preferably 10 ° C to 100 ° C, usually about 0.1 to 72 hours, preferably 0.3 to 24 hours. Can be about.
  • R 2 , R 3 , R A , A, m, and w are as defined above, and R lb is halogen, alkyl, haloalkino, anoreke-nore, haloanoreke-nore, anorequino-nore, noroanore-nore , Hydroxy, anolecoxy, haloanorecoxy, honoreminore, anorequinolecanoleboninole, noroanorequinolecanonolenore, force ruboxyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano Nitro, amino, alkylamino, dialkylamino, optionally substituted phenoxy, optionally substituted pyridyloxy, optionally substituted phenoxycarbon or optionally substituted pyridyloxycarbonyl.
  • Examples of the fluorine compound in the reaction [G] include inorganic fluorides such as lithium fluoride, sodium fluoride, potassium fluoride, cesium fluoride, silver fluoride, and tetrabutyl ammonium fluoride. 1 type or 2 types or more can be appropriately selected.
  • the fluorine compound can be used in an amount of 1 to 30 times mol, preferably 1 to 15 times mol for the compound of formula (I-7).
  • a crown ether such as 18-crown 1-ether may be used.
  • the reaction [G] can usually be carried out in the presence of a solvent.
  • a solvent any solvent inert to the reaction may be used.
  • any solvent inert to the reaction may be used.
  • jetyl ether butyl ether.
  • Ethers such as monotel, tetrahydrofuran, dioxane and dimethoxyethane; halogenated hydrocarbons such as black benzene, dichlorobenzene, dichloromethane, black mouth form, carbon tetrachloride, dichloroethane, trichloroethane and dichloroethylene;
  • Aromatic hydrocarbons such as benzene, toluene, xylene; and polar aprotic solvents such as acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethylsulfoxide, dimethylacetamide, ⁇ -methylpyrrolidone, etc. 1 type or 2 types or more can be
  • the reaction can usually be carried out at 10 to 150 ° C, preferably 0 to 100 ° C, and the reaction time is usually about 0.1 to 24 hours, preferably about 0.2 to 12 hours. Can do.
  • R 2 , R 3 , A, R A , m and w are as described above, and R le is halogen, alkyl, haloalquinole, anorekeninore, haloanorekeninore, anorequininore, noroanorequininore, trianorequinoresinole lechur , Hydroxy, alkoxy, haloalkoxy, formyl, alkyl carbonyl, haloalkyl carbonyl, carboxyl, aminocarbonyl, alkylamino carbonyl, dialkylaminocarbonyl, nitro-containing nitro, ami-containing alkylamino, dialkyl-amino They are optionally substituted phenoxy, optionally substituted pyridyloxy, optionally substituted phenoxycarbol or optionally substituted pyridyloxycarbol.
  • Examples of the base in the reaction [H] include potassium trimethylsilanolate, lithium thiomethoxide, sodium phenol selenide and the like, and preferably 1 to 30 times mol, preferably the compound of the formula (1-9) 1 to 5 times mol can be used.
  • the reaction] can usually be carried out in the presence of a solvent.
  • a solvent any solvent inert to the reaction may be used.
  • ethers such as jetyl ether, butyl ether ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; and acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric
  • polar non-protonic solvents such as triamide, dimethylacetamide, and ⁇ ⁇ ⁇ -methylpyrrolidone.
  • the reaction [ ⁇ ] can usually be carried out at 0 to 150 ° C, preferably 10 to 100 ° C, and the reaction time is usually about 0.1 to 72 hours, preferably about 0.5 to 48 hours. can do.
  • R is a fluorine atom, a chlorine atom, an alkyl, a halo anoquinolole, a hydroxy, an alkoxy, a haloalkoxy, a honoreminore, an alkyl carbonyl, a noro anorecanole bonenore , Force noreboxinole, anorecoxicanoleboninole, ro, roanorexoxy decanoyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, amidoalkylamido dialkylamido, optionally substituted phenoxy, substituted V, pyridyloxy, substituted, phenoxycarbol or may be substituted !, pyridyloxycarbon, R 2b is a hydrogen atom, a fluorine atom, a chlorine atom, an alkyl, a halo
  • Reaction [I] is carried out by reacting the compound of formula (1-11) with hydrogen gas in the presence of a catalyst.
  • catalysts that can be used include noradium carbon, platinum oxide, and Raney nickel. It can be selected appropriately.
  • the catalyst can be used in an amount of 0.001 to 1.0 times, preferably 0.01 to 0.3 times the weight of the compound of formula (1-11).
  • Reaction [I] can be normally performed in presence of a solvent.
  • Any solvent may be used as long as it is inert to the reaction.
  • ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane.
  • Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; alcohols such as methanol, ethanol, propanol, normal butanol, tertiary butanol; benzene, toluene, xylene Aromatic hydrocarbons; polar aprotic solvents such as acetonitrile, propiotolyl, ⁇ , ⁇ -dimethylformamide, dimethylacetamide, ⁇ -methylpyrrolidone; such as methyl acetate, ethyl acetate, propyl acetate 1 type or 2 or more types can be suitably selected from such esters; ketones such as acetone, jetyl ketone, methyl ethyl ketone, and methyl isobutyl ketone; acetic acid; and water.
  • Reaction [I] can be usually carried out at 0 to 150 ° C, preferably 10 to: L00 ° C, and the reaction time is usually about 0.1 to 72 hours, preferably about 0.5 to 48 hours. Can do.
  • R ⁇ R 2a, R 3a, A, m, w and X are as defined above, R 4 is hydrogen atom or alkyl.
  • Carbon monoxide in the reaction Ci] can be used in an amount of 1 to 200-fold mol, preferably 1 to 50-fold mol based on the compound of the formula (1-1).
  • R 4 —NH in the reaction (i) examples include ammonia, methylamine, and ethylamine.
  • R 4 —NH is 1 to 50 times mol, preferably 1
  • Reaction ⁇ can usually be carried out in the presence of a palladium catalyst.
  • the palladium catalyst include tetrakistriphenylphosphine palladium, bistriphenylphosphine palladium dichloride, palladium acetate, palladium acetate monotriphosphine, palladium acetate 1,4-bis (diphenylphosphino) butane, palladium chloride, chloride Palladium tritertiary butylphosphine and the like can be mentioned, and one or more can be selected as appropriate. It is used in a proportion of 0.001 to 0.1 equivalents relative to the compound of formula (g 1).
  • tertiary phosphines such as triphenylphosphine and tri- (0-tolyl) phosphine may coexist, and 0.001-0.1 against the compound of formula (1-1) Used in equivalent proportions.
  • Examples of the base used in the reaction ⁇ include inorganic bases such as sodium carbonate and potassium carbonate; organic amines such as triethylamine, tributylamine and diisopropylamine.
  • the amount of the compound of formula (1-1) is usually 1.0 to 30 equivalents, desirably 1.0 to 15 equivalents.
  • the reaction Ci] can usually be performed in the presence of a solvent.
  • the solvent may be any solvent that is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • fats such as hexane, heptane, octane and cyclohexane.
  • Hydrocarbons such as jetinoreethenole, butinoleethinoleethenole, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethylsulfoxide,
  • One or more polar aprotic solvents such as oxamethylphosphoric triamide, sulfolane, dimethylacetamide and ⁇ ⁇ ⁇ -methylpyrrolidone can be appropriately selected.
  • the reaction Ci] can be usually carried out at 0 to 150 ° C, preferably 10 to: LOO ° C, and the reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. it can.
  • RR 2 R 3a A, m, w and X are as described above, and R 5 is alkyl.
  • Carbon monoxide in the reaction [K] can be used in an amount of 1 to 200 times mol, preferably 1 to 50 times mol, of the compound of the formula (1-1).
  • R 5 —OH in the reaction [ ⁇ ] for example, methanol, ethanol, propanol, isopropyl alcohol, butanol and the like can be used.
  • R 5 —OH can be used in an amount of 1 to 50 times mol, preferably 1 to 10 times mol, of the compound.
  • Reaction [K] can be normally performed in presence of a palladium catalyst.
  • the palladium catalyst include tetrakistriphenylphosphine palladium, bistriphenylphosphine, ⁇ radium dichloride, palladium acetate, palladium acetate-triphenylphosphine, palladium acetate-1,4-bis (diphenylphosphino).
  • Butane, palladium chloride, palladium chloride-tritertiary butylphosphine, etc. Can. It is used in a proportion of 0.001 to 0.1 equivalent relative to the compound of formula (ii).
  • a palladium catalyst When a palladium catalyst is used, 0.001 to 0.1 equivalents to the compound of formula (1-1) in which tertiary phosphines such as triphenylphosphine and tri (0-tolyl) phosphine may coexist Used in percentage.
  • tertiary phosphines such as triphenylphosphine and tri (0-tolyl) phosphine may coexist Used in percentage.
  • Examples of the base used in the reaction [ ⁇ ] include inorganic bases such as sodium carbonate and potassium carbonate; organic amines such as triethylamine, tributylamine and diisopropylamine.
  • the amount of the compound of formula (1-1) is usually 1.0 to 30 equivalents, preferably 1.0 to 15 equivalents.
  • the reaction [ii] can usually be carried out in the presence of a solvent.
  • the solvent may be any solvent inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; aliphatics such as hexane, heptane, octane and cyclohexane Hydrocarbons; ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl, ⁇ , ⁇ —dimethylformamide, dimethyl sulfoxide, hexamethylphos
  • polar aprotic solvents such as holic triamide, sulfolane, dimethylacetamide, and ⁇ ⁇ ⁇ -methylpyrrolidone.
  • the reaction [ ⁇ ] is usually 0 to 150 ° C, preferably 10 to: LOO ° C, and the reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. Can do.
  • R is halogen, alkyl, haloalkyl, alkyne nynore, haloanorekeninore, anorequininore, haloanorequininore, trianolenoquinosylinoretininore, hydroxy , Alkoxy, haloalkoxy, formyl, alkylcarbonyl, haloalkylcarbonyl, carboxyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cyano, amino, alkylamino, dialkylamino, substituted R may be a hydrogen atom, a halogen atom, an alkyl, a haloalkyl, an alkoxy, an optionally substituted pyridine, an optionally substituted pyridoxy, an optional
  • the compound of the formula (1-15) is usually catalytically hydrogenated with a metal catalyst in a hydrogen atmosphere at normal pressure to several atmospheres in the presence of a solvent, or in an acidic solvent. Reduction can be achieved by the action of a metal catalyst.
  • the metal catalyst include nodium carbon, acid white, and the like.
  • One or more kinds can be appropriately selected from gold, Raney nickel, iron, salt stannic acid, and the like.
  • [L] Hydrogen in the reaction can be used in an amount of 1 to 200 times mol, preferably 1 to 50 times mol for the compound of formula (1-15).
  • any solvent inert to the reaction may be used, for example, water; acetic acid; ethyl acetate; alcohols such as methanol, ethanol, propanol, normal butanol and tertiary butanol; Ethers such as butyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene and xylene; and pentane, hexane, heptane, octane and cyclohexane.
  • acetic acid such as methanol, ethanol, propanol, normal butanol and tertiary butanol
  • Ethers such as butyl ether, tetrahydrofuran, dioxane and dimethoxyethane
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • the reaction [L] can usually be carried out at ⁇ 10 to 100 ° C., preferably 0 to 80 ° C.
  • the reaction time is usually about 0.5 to 24 hours, preferably about 2 to 12 hours. it can.
  • the compound of formula (II) or formula (III) of the reaction [A] is a known compound, or can be produced according to known materials.
  • the compound of the formula (II) can be produced according to the method described in Synthesis, 1 980, page 505 or a method similar thereto, and the compound of the formula (III) is described in US 5082949, WO03Z24222. It can be produced according to the methods described in Schemes 9 to 22 or in accordance therewith.
  • the compound of formula (III) includes a novel compound.
  • the compound can be produced, for example, according to the following reaction [M].
  • V is halogen
  • the compound of formula (VIII) can be synthesized by allowing an equimolar amount of hydrazine to act on the compound of formula (VII) in the presence of a solvent.
  • Any solvent can be used as long as it is inert to the reaction.
  • water acetic acid
  • alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol
  • jetyl ether butyl Ethers such as ethyl ether, tetrahydrofuran, dioxane and dimethoxyethane
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • One or more of aliphatic hydrocarbons can be selected as appropriate.
  • the first step of the reaction [ii] is usually performed in the presence of a base.
  • a base one or more kinds can be appropriately selected from potassium carbonate, sodium carbonate, sodium acetate, sodium hydride, sodium alkoxide, sodium thioalkoxide and the like.
  • the amount used is 0.8 to 4 times mol, preferably 1 to 2 times mol for the compound of formula (VII).
  • the first step of the reaction [ii] can be usually performed at 0 to 140 ° C, preferably 20 to 100 ° C,
  • the reaction time is usually about 0.5 to 24 hours, preferably about 2 to 12 hours.
  • the second step of the reaction [M] can be performed by allowing a base to act on the compound of the formula (VIII) in the presence of a normal solvent.
  • a base for example, one or more kinds can be appropriately selected from potassium carbonate, sodium carbonate, sodium hydride, sodium alkoxide, sodium thioalkoxide and the like.
  • the base is used in an amount of 0.8 to 4 times mol, preferably 1 to 2 times mol for the compound of formula (VIII).
  • ethers such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; and acetonitrile, propio-tolyl, ⁇
  • polar aprotic solvents such as ⁇ -dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, and ⁇ -methylpyrrolidone.
  • the second step of the reaction [v] can be usually carried out at 0 to 150 ° C, preferably 50 to 110 ° C, and the reaction time is usually about 0.5 to 24 hours, preferably 1 to 12 hours. It can be about hours.
  • the third step of the reaction [M] can usually be carried out by oxidizing the compound of the formula (IX) with an oxidizing agent in the presence of a solvent.
  • the oxidizing agent can be appropriately selected from, for example, power permanganate, sodium chlorite and the like.
  • the oxidizing agent can be used in an amount of 1 to 20 times mol, preferably 2 to 10 times mol for the compound of formula (IX).
  • sodium chlorite is used as the oxidizing agent
  • sodium dihydrogen phosphate is used in an amount of 1 to 20 times mol, preferably 2 to 10 times mol, of the compound of formula (IX).
  • the solvent one or more can be appropriately selected from water, acetonitrile, propiotolyl, acetone and the like.
  • the third step of the reaction [M] can usually be carried out at ⁇ 10 to 100 ° C., preferably 0 to 80 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably about 2 to 20 hours. It can be.
  • the compound of the formula (IV) in the reaction [B] is a known compound, or can be produced according to known materials.
  • the compound of formula (IV) is Org. Prep. Proceed. Int., 199 It can be produced according to the method described in 3 years, 25%, page 585, the method described in schemes 8 to 10 in WO03Z24222, or the like.
  • the compound of formula (V) in the reaction [B] includes a novel compound.
  • the compound is Gabrie
  • A is as described above, T is halogen, —OSO G (G is a sulfonic acid ester residue) or
  • T is — OH
  • M is a hydrogen atom.
  • examples of the sulfonate residue may be substituted with C alkyl such as methyl and ethyl, and C alkyl.
  • Examples include ferrules.
  • T is halogen or —OSO G
  • M is sodium or
  • ethers such as diethyl ether, butyl ether, tetrahydrofuran, dioxane and dimethoxyethane
  • aromatics such as benzene, toluene and xylene.
  • Aromatic hydrocarbons such as acetonitrile, propio-tolyl, ⁇ , ⁇ dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, ⁇ ⁇ ⁇ methylpyrrolidone; and
  • One or more kinds can be appropriately selected from alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol.
  • T is halogen or —OSO G
  • M is sodium or
  • reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. it can.
  • the first step of the reaction [N] is usually a force that can be performed according to the Mitsunobu method when T is -OH and M is a hydrogen atom. It can be carried out using luazodicarboxylate and triphenylphosphine.
  • the dialkylazodicarboxylate and triphenylphosphine can be used in an equimolar amount with respect to the compound of formula (X). Examples of the dialkylazodicarboxylate include jetinoreazodicanoloxylate, diisopropinoreazodicanoloxylate, and the like.
  • the solvent may be any solvent that is inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene
  • Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene
  • aromatic hydrocarbons such as benzene, toluene, xylene, etc. It can be selected appropriately.
  • the first step of the reaction [N] can be carried out usually at 0 to 80 ° C., preferably 20 to 60 ° C. when T is —OH and M is a hydrogen atom, and the reaction time is Usually, about 0.5 to 24 hours, preferably about 1 to 16 hours can be used.
  • the second step of the reaction [N] can usually be performed by decomposing the compound of the formula (XII) using hydrazine in the presence of a solvent.
  • the hydrazine can be usually used in an equimolar amount with respect to the compound of the formula (XII).
  • any solvent may be used as long as it is inert to the reaction.
  • ethers such as diethyl ether, butyl ether, tetrahydrofuran, dioxane and dimethoxyethane; aromatics such as benzene, toluene and xylene.
  • One or two or more types can be appropriately selected from group hydrocarbons; alcohols such as methanol, ethanol, propanol, nonolemanolebutanol and tertiary butanol.
  • the second step of the reaction [N] can be usually carried out at 0 to 140 ° C, preferably 30 to 100 ° C, and the reaction time is usually about 0.5 to 24 hours, preferably about 2 to 12 hours. can do.
  • the compound of the formula (V) can also be produced according to the following reaction [0].
  • ⁇ is a hydrogen atom or alkyl
  • J is — ⁇ or — OG 1 (G 1 is an ether residue)
  • n is 1 or 2
  • examples of G 1 include, for example, methyl, ethyl Like C Archi
  • Examples thereof include 1-6 and fur optionally substituted with C alkyl.
  • the first step of the reaction [0] can be usually performed in the presence of a solvent.
  • any solvent may be used as long as it is inert to the reaction.
  • etherols such as diethyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane; black benzene, dichlorobenzene, dichloromethane, Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitryl, propio-tolyl, ⁇ , ⁇ ⁇ ⁇ -dimethylformamide , Dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, dimethylacetamide, polar aprotic solvents such as methyl pyrrolidone; methanol, ethanol, propanol, normal butanol, tertiary rib Alcohol
  • the first step of the reaction [0] can usually be carried out at 0 to 150 ° C, preferably 30 to 110 ° C, and the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. can do.
  • the compound of formula (XV) is usually used in the presence of a solvent using a reducing agent. It can be done more than anything.
  • a reducing agent for example, one or more of lithium aluminum hydride and sodium borohydride can be appropriately selected.
  • any solvent that is inert to the reaction may be used.
  • examples include ethers such as jetinoreethenore, butinoreethinoreethenole, tetrahydrofuran, dioxane, and dimethoxyethane. 1 type or 2 types or more can be appropriately selected.
  • the compound of formula (XV) is usually reduced by catalytic hydrogenation with a metal catalyst in a hydrogen atmosphere at atmospheric pressure to several atmospheres in the presence of a solvent.
  • a metal catalyst one or more kinds can be appropriately selected from, for example, noradium carbon, platinum oxide, Raney nickel and the like.
  • any solvent that is inert to the reaction may be used.
  • water acetic acid
  • ethyl acetate alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol
  • Ethers such as jetyl ether, butyl ether, tetrahydrofuran, dioxane, dimethoxyethane
  • halogenated compounds such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, trichloroethane, dichloroethylene Hydrocarbons
  • 1 or 2 aromatic hydrocarbons such as benzene, toluene, xylene
  • aliphatic hydrocarbons such as pentane, hexane, heptane, otatan, cyclohexane, etc.
  • the second step of the reaction [0] can usually be carried out at ⁇ 10 to 100 ° C., preferably 0 to 80 ° C., and the reaction time is usually about 0.5 to 24 hours, preferably 2 to It can be about 12 hours.
  • the compound of formula (V) can be removed as a salt by adding an acid to the reaction solution in the production process.
  • the pest control agent containing the compound of the present invention is, for example, each problematic in the field of agriculture and horticulture. It is particularly useful as a species pest control agent, that is, an agricultural and horticultural pest control agent, or a pest control agent that parasitizes animals, that is, an animal parasite control agent.
  • Pesticides for agricultural and horticultural use include, for example, power useful as insecticides, acaricides, nematicides, and soil-killing insecticides.
  • Namihada, -Senamihada-, Kanzahadada, Mikanhada Plant parasitic mites such as apple hada, chiyanokorida, mandarin orange, mite, etc .; diamondback moth, weevil, lotus root, codling moth, ball worm, cigarette budworm, maiiga, kono noiga, chinokokakumonhamaki , Momoshin Taiga, Nashihime Shinchii, Tamanayaga, Power Braga, Colorado potato beetle, Urihamushi, Ballui bilbil, Aphids, Pruners, leafhoppers, scale insects, stink bugs, whiteflies, thrips, beetles, beetles Such as moss, ants, and clams Agricultural insect pests; plant parasitic mites
  • Stomach pests such as gastropods, isopods such as stag beetle, bark beetle, hygiene pests such as house dust mites, house flies, cayenne powers, cockroaches, etc .; Stored pests such as moss; clothing, house pests such as Iga, Himekatsubushimushi, termites, etc .; effective for the control of indoor dust mites such as Pterodactylidae, Scarlet Mite, Southern Mite .
  • the agricultural and horticultural harmful organism control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like.
  • the agricultural and horticultural pesticide containing the compound of the present invention is also effective for controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents.
  • drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents.
  • the compound of the present invention has excellent osmotic transfer properties, by treating the soil with a pesticide for agricultural and horticultural use containing the compound of the present invention, soil harmful insects, mites, nematodes In addition, it can control pests in the foliage at the same time as the control of gastropods and isopods.
  • the pest control agent containing the compound of the present invention is that the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. And pesticides for agricultural and horticultural use.
  • the agricultural and horticultural pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, oily mixture of the compound and various agricultural adjuvants. Used in various forms such as suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc. It can be in any formulation form.
  • Adjuvants used in the formulation include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, mixture of olinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium nitrate, zeolite, starch, etc.
  • Mold carrier water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, black benzene, cyclohexane, dimethyl sulfoxide, ⁇ , ⁇ -dimethylformamide, dimethylacetamide, ⁇ -methyl-2 —
  • Solvents such as pyrrolidone and alcohol; fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkylsulfate esters, alkylsulfates, alkylaryl sulfates, alkyldiglycols Ether sulfate , Alcohol sulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignite sulfonate, alkyl diphenyl ether
  • 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.
  • auxiliary agents they can be appropriately selected from those known in the art.
  • various commonly used adjuvants such as extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, safeners, and antifungal agents.
  • the compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.9 99 to 95: 5, preferably 0.005: 99.995 to 90:10.
  • a diluent such as water
  • various spreading agents surfactants, vegetable oils, mineral oils, etc.
  • the application of the agricultural and horticultural pesticide containing the compound of the present invention cannot be generally specified due to differences in weather conditions, formulation, application time, application location, pest type and occurrence, etc.
  • the active ingredient concentration is 0.05 to 800,000 ppm, preferably 0.5 to 500,000 ppm.
  • the application amount per unit area is 0.05 to 50 000 g, preferably 1 to 30000 g, of the present compound per hectare.
  • application of the agricultural and horticultural pest control agent which is another preferred embodiment of the pest control agent containing the compound of the present invention, is performed in accordance with the application of the pest control agent.
  • the present invention also includes a method for controlling pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.
  • Various formulations of the agricultural and horticultural pesticide containing the compound of the present invention, or a diluted product thereof, are usually applied by a commonly used application method, ie, spraying (eg spraying, spraying, misting, Atomizing, dusting, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc.
  • spraying eg spraying, spraying, misting, Atomizing, dusting, water surface application, etc.
  • soil application mixtureing, irrigation, etc.
  • surface application application, powder coating, coating, etc.
  • immersion poison bait etc.
  • livestock a mixture of the above-mentioned active ingredients in feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in their excreta.
  • ultra-low volume method In this method, it is possible to contain 100% of the active ingredient.
  • the agricultural and horticultural pesticide containing the compound of the present invention can be used in combination with or combined with other agricultural chemicals, fertilizers, safeners, etc. May show sex.
  • Other pesticides include herbicides, insecticides, acaricides, nematicides, soil pesticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done.
  • a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve.
  • 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 may be used by preparing both together.
  • the present invention also includes such a mixed pest control composition.
  • the mixing ratio of the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be specified unconditionally due to differences in weather conditions, formulation form, application time, application location, pest type and occurrence, etc. Generally, it is 1: 300 to 300: 1, preferably 1: 100 to 100: 1.
  • the appropriate amount to be applied is 0.1 to 50000 g, preferably 1 to 30000 g as the total amount of active ingredient compounds per hectal.
  • the present invention also includes a method for controlling pests by a method for applying such a mixed pest control composition.
  • insecticides as an active ingredient compound (generic name; including some pending applications) of insecticides, acaricides, nematicides or soil insecticides, that is, pest control agents, Profenofos, Cyclonorevos, Dichlorvos, Fenitrothion, EPN, Diazinon, Chlorpyrif os-methyl, Acephate, Prothiofos , Phosthiazate (Fosth iazate), Phosphocarb (Chosphofos), Cadusafos, Disulfoton (Chlorpyrifos), Demeton-S-methyl, Dimethoate, Dimethoate, Methidophos (Metidophos) Organophosphate compounds such as Parathion; Carbaryl, Propoxur, Aldicarb ), Carboforan, Thiodicarb, Methomyl, Oxamyl, Ethiofencarb, Pirimi
  • Organochlorine compounds such as Dicofol, Tetradifon, Endosulfan; Organometallic compounds such as Fenbutatin Oxide; Fenvalerate, Permethrin, Pyrethroid compounds such as Cypermet hrin, Deltamethrin, Cyhalothrin, Tefluthrin, Etofenprox, Fenpropathrin, Bifenthrin; Diflubenzuron, Chlorfluazuron, Teflubenzuron, Flufenoxuron, Lufenuron, Novaluron, Bistrifluron, Noviflumuron Nabenzo Lurea system Juvenile hormone-like compounds such as Methoprene, Pyriproxyfen, Fenoxycarb; Pyridazinone compounds such as Pyridaben; Fenpyroximate, Fipronil, Tebufenpyrad Pyrazole compounds such as Tebufe npyrad, Ethiprole, Tolfenpyrad, Acetoprole,
  • Other compounds include Flonicamid, Buprofezin, Hexythiazox, Amitraz, Chlordimefor m, Silafluofen, Triazamate ), Pymetrozin e, Pyrimidifen, Chlorfenapyr, Ind oxacarb, Acequinocyl, Etoxazole, Cyrom azine, 1,3- (1,3-dichloropropene), Diafenthiur on), Benclothiaz, Flufenerim, Pyridalyl, Spirodiclofen, Bifenazate, Spiromesifen, Propargite, Clofentez, Clofentez Examples of such compounds include Fluacrypyrim, Flubendiamide, Cyflu metofen, Metaflumizone, Amidoflumet, and the like.
  • microbial pesticides such as BT agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents; avermectin, emamectin-benzoate, minolemectin, Antibiotics such as Spinosad, Ivermectin and Lepimectin; natural products such as Azadirachtin and Rotenone can be mixed and used together.
  • BT agents entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents
  • avermectin emamectin-benzoate, minolemectin
  • Antibiotics such as Spinosad, Ivermectin and Lepimectin
  • natural products such as Azadirachtin and Rotenone
  • mepa-pyrim Melpanipyrim
  • pyrimethanil pyrimethanil
  • cyprodil Cy prodinil
  • Pyrimidinamine compounds such as: Triadimefon, Bitertanol, Triflumizole, Etaconazole, Propiconazole, Penconazole, Penoleazole (Flusilazole), Microbutanol (Myclobutanil), Cyproconazole, Cybuconazole, Terbuconazole, Hexaconazole, Furcon azole-cis, Prochloraz, M, Prochloraz, M Epoxyconazo nore (Epoxiconazole), Atofconan nore (Tetraconazole), Yayoshokonazo Azole compounds such as Oxpocona zole and Sipconazole; Quinoxaline compounds such as Quinomethionate; Maneb, Zine
  • Isoprothiolane Tricyclazole, Pyroquilon, Diclomezine, Probenazole, Quinoxyfen, Propamocarbole hydrochloride, and Propamocarb Hydrochloride.
  • examples thereof include spiroxamine, chloropicrin, dazomet, and metam-sodium.
  • pesticides that can be used in combination with or combined with the compounds of the present invention include, for example, active compounds of herbicides such as those described in the Farm Chemicals Handbook (2002 edition), particularly those treated with soil. There are things.
  • animal parasite control agents include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestinal tract, lung, It is effective for the control of endoparasites parasitic on the heart, liver, blood vessels, subcutaneous, lymphoid tissue, etc., but it is particularly effective for the control of ectoparasites.
  • ectoparasites include animal parasitic mite fleas. These types are very difficult to list, so here are some examples.
  • Animal parasitic mites include, for example, Boophilus microplus, Rnipicephalus sanguineus, Haemaphvsalis longicorni s, and Tematani (Haemaphvsalis flava) campanula ta, chair power (Haemaphvsalis concinna), hamatophvsalis iap onica, sinker "Haemaphvsalis ias, mite (Ixodes ovatus, tick) Ticked ticks (Ixodes persulcatus), Takasago Kiraramagini (Amblvomma testudinarium), gifted Togenamatani (Haemaphvsalis megaspinosa), Aminakakumaguji (Dermacentor r eticulatus); Trisanta-(Ornithonvssus svlviarum, Na Trisantani (Ornith avian mite
  • fleas for example, ectoparasite worms belonging to the order Flea (Siphonaotera), more specifically fleas belonging to the family Flea (Pulicidae), Nagano (CerateDhyllus), etc. .
  • Examples of fleas belonging to the family Fleas include: Fleafish (CtenoceDhalides canis), Nekono (CtenoceDhalides felis), Humanfish (Pulex irritans), Nite trout flea (Echidnoph aga gallinacea), Examples include fleas (Leptopsvl la seenis), yosokuchinonosuno (Nosopsyllus fasciatus), and Yamatonezuno (Monopsvll us ank).
  • the animal parasite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family flea family, especially cynomolgus, cat flea and the like.
  • ectoparasites include, for example, lice such as white lice, white lice, white lice, white lice, head lice; white lice such as white lice; blood sucking such as Usiab, Uinu power, and Thometgebu Diptera pests.
  • endophytic organisms include nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms; Crustacea, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke-like fluke; kokujimu, malaria parasite, intestinal floriformus, toxoplasma Protozoa such as Cryptosporidium.
  • nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms
  • Crustacea multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms
  • Japanese schistosomiasis fluke-like fluke
  • kokujimu malaria parasite, intestinal floriformus, toxoplasma Protozoa such as Cryptosporidium.
  • Examples of host animals include various pets, livestock, poultry, and the like.
  • the animal parasite control agent containing the compound of the present invention is effective for the control of pests parasitic on pet animals or livestock, particularly ectoparasites. It is especially effective for dogs, cats, ushi or horses in pets or livestock.
  • the compound of the present invention When used as an animal parasite control agent, it may be used as it is. Also, powders, granules, tablets, powders, capsules, liquids, emulsions, aqueous suspensions together with appropriate auxiliary agents. In addition, it can be used in various forms such as an oily suspension. In addition to the above-mentioned preparation form, any preparation form that is generally used in this field can be used as long as it is suitable for the purpose of the present invention. Examples of the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the aforementioned preparation adjuvants for agricultural and horticultural pest control agents such as cetyltrimethylammonium bromide.
  • Cationic surfactants water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol , Benzenoreanoleconole, Ethylene glycol, Propylene glycol, Polyethylene glycol, Liquid polyoxyethylene glycol nore, Butinoresin glycol nore, Ethylene glycol nole monomethinoatenore, Ethyleneglycoleno monoethylenoatenore, Diethylene glycol Solvents such as ricinole monoethylenoate, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; butylhydroxyl-sol, butyhydroxytoluene, ascorbic acid, sodium metabisulfite
  • each component of these adjuvants can be used by appropriately selecting one or more types without departing from the object of the present invention.
  • they can be used by appropriately selecting from those known in the field, and moreover, various adjuvants used in the above-mentioned agricultural and horticultural fields as appropriate. You can also select and use.
  • the compounding ratio of the compound of the present invention to various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. It can be used as a supplement.
  • the compound of the present invention is administered to the host animal orally or parenterally.
  • 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.
  • parenteral administration method for example, the compound of the present invention is prepared in an appropriate formulation and then taken into the body by intravenous injection, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on ) Treatment, pour-on treatment, spray treatment, and the like; and a method of embedding a fat slice 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, purpose of administration, disease symptoms, etc., but is generally O.Olmg to: L00g relative to the body weight lKg of the host animal, preferably 0.1 It is appropriate to administer at a rate of mg to 1 Og.
  • the present invention also includes a method for controlling pests by the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.
  • the present invention includes a prophylactic or therapeutic agent for parasite-derived animal diseases comprising the compound of the present invention as an active ingredient, and a method for preventing or treating parasite-derived animal diseases.
  • the compound of the present invention When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretic agents, sedatives, anti-inflammatory agents, bactericides, and coloring agents together with adjuvants. , Fragrances, preservatives and the like can be mixed or used together. If necessary, mix with or use other animal drugs and pesticides such as anthelmintics, anti-coxime, insecticides, acaricides, fleas, nematicides, bactericides, and antibacterials. Can be one in this case The layer may show an excellent effect.
  • the present invention includes a mixed pest control composition in which various components as described above are mixed or used together, and a pest control method using the composition, particularly control of ectoparasites or endoparasites. A method is also included.
  • the aqueous layer was acidified with dilute hydrochloric acid and extracted with ethyl acetate.
  • the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure, and the precipitated crystals were washed with hexane to obtain 0.05 g of the desired product having a melting point of 227 to 232 ° C.
  • reaction mixture was poured into water and extracted with ethyl acetate.
  • organic layer was washed with saturated brine, dried over anhydrous sodium sulfate.
  • the solvent was distilled off under reduced pressure.
  • 0.54 g of triethylamine is gradually added dropwise to a mixture of 0.41 g of 1-cyclopropylethylamine hydrochloride and 5 ml of tetrahydrofuran, and then stirred for 35 minutes at room temperature.
  • Benzoyl chloride prepared in the following way: 3-methyl-2-trobenzoic acid 0.5 g and methylene chloride 6 ml in a mixed solution of 0.7 ml of sodium oxalyl and 2 drops of dimethylformamide at room temperature 1 After stirring for 5 hours, a mixture of 5 ml of tetrahydrofuran and 5 ml of tetrahydrofuran was added dropwise under ice-cooling.
  • the mixed solution was extracted twice with 30 ml of ethyl acetate, and the organic layer was slowly added to a mixed solution of 4 g of sodium disulfite and 50 ml of water at 20 ° C. or lower with stirring.
  • the organic layer was separated, and the aqueous layer was extracted with 30 ml of ethyl acetate.
  • the organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure.
  • the produced crystal was recrystallized from methylene chloride and hexane to obtain 0.67 g of the desired product.
  • A5 represents -CH- [c-Pr (l-Me)]
  • A6 represents -CH (Me)-[c-Bu].
  • e is a methyl group
  • Et is an ethyl group
  • Pr is a propyl group
  • i_Pr is an isopropyl group
  • c-Pr is a cyclopropyl group
  • c-Bu is a cyclobutyl group
  • Ph is a phenyl group
  • Py Each represents a pyridyl group.
  • c-Pr (2-Me) is a cyclopropyl group substituted with a methyl group at the 2-position
  • OPh (4-F) is a phenyl group.
  • the 4-phenyoxy group is substituted with a fluorine atom at the 4-position
  • 2-OPy (5-Cl) is a 2-pyridyloxy group substituted with a chlorine atom at the 5-position of the pyridyl group. The description also applies to this.
  • Test example 1 Effectiveness test for Lotus monto
  • Cabbage leaf pieces were immersed for about 10 seconds in a chemical solution prepared so that the concentration of the compound of the present invention was 50 ppm, and air-dried. Place a damp filter paper on a petri dish with a diameter of 9 cm and air-dry it on it. Placed cabbage leaf pieces. To that end, we released 10 larvae of 2 to 3 years old, and capped them and left them in a constant temperature room at 25 ° C. On the 5th day after the release, the mortality was determined and the mortality rate was calculated by the following formula. Abnormal insects were also considered dead.
  • Test Example 2 Effect test on silver leaf whitefly
  • Control value (%) (l-((Ta X Cb) / (Tb X Ca))) X 100
  • Ta Number of old larvae after treatment in the treatment area + number of pupae
  • Tb Number of hatching larvae before treatment in the treated area
  • the leaves of green beans that have been uniformly laid with the eggplant sprouts are soaked in a chemical solution prepared so that the concentration of the compound of the present invention is 50 ppm, and air-dried. Place a damp filter paper on a plastic cup 9 cm in diameter and 4 cm in height, and place an air-dried leaf bean leaf on it. Then, close the lid and leave it in a constant temperature room at 25 ° C. After 6 to 8 days of treatment, the number of old larvae and the number of pupae is investigated, and the control value is obtained by the following formula.
  • the compound of the present invention exhibits a high control effect.
  • Control value (%) (1 ((Number of old larvae in treated area + number of pupae) Z (Number of old larvae in untreated area + ⁇ ))) X 100
  • the above is uniformly mixed to form a powder.
  • the mixture of the above components and the compound of the present invention are mixed at a weight ratio of 4: 1 to obtain a wettable powder.
  • the above ingredients are mixed uniformly to form a solution.
  • novel anthranilamide-based compound of the present invention has a low dosage and has a very high control effect against pests, and can be used as an agricultural and horticultural pest control agent and animal parasite control agent.
  • the entire contents of the specification, claims, and abstract of Japanese Patent Application 2005-017358 filed on January 25, 2005 are hereby incorporated by reference. It is something that is incorporated.

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Abstract

La présente invention décrit un nouvel agent pesticide. La présente invention décrit notamment un composé de type anthranilamide de formule (I) ci-dessous, ou un sel dudit composé. (I) (Dans la formule, R1 représente un atome d'halogène, un groupement alkyle ou un groupement similaire ; R2 représente un atome d'hydrogène ou d'halogène, un groupement alkyle ou un groupement similaire ; R3 représente un atome d'halogène, un groupement alkyle ou un groupement similaire ; A représente un groupement alkyle substitué par Y ; Y représente un groupement cycloalkyle en C3-C4 éventuellement substitué par au moins un substituant sélectionné au sein du groupe constitué par les atomes d'halogène, les groupements alkyle et les groupements halogénoalkyle ; m représente un nombre compris entre 0 et 4 inclus ; et w représente un nombre compris entre 0 et 5 inclus.)
PCT/JP2006/301057 2005-01-25 2006-01-24 Composé de type anthranilamide, méthode de synthèse dudit composé et agent pesticide contenant ledit composé WO2006080311A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009113712A2 (fr) * 2008-03-13 2009-09-17 Ishihara Sangyo Kaisha, Ltd. Compositions pesticides
WO2010010958A2 (fr) * 2008-07-24 2010-01-28 Ishihara Sangyo Kaisha, Ltd. Composition pesticide
CN102060770A (zh) * 2010-12-27 2011-05-18 浙江工业大学 一种邻甲酰胺基苯甲酰胺类化合物及中间体的制备与应用
CN102617551A (zh) * 2012-03-08 2012-08-01 华东理工大学 含二氟(亚)甲基邻甲酰胺基苯甲酰胺类化合物
WO2015184229A1 (fr) * 2014-05-29 2015-12-03 E. I. Du Pont De Nemours And Company Procede pour la preparation de l'acide 3-methyl-2-nitrobenzoïque par l'oxydation a l'air
KR101811897B1 (ko) * 2010-04-27 2017-12-22 스미또모 가가꾸 가부시키가이샤 유해 생물 방제 조성물 및 그의 용도

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004067528A1 (fr) * 2003-01-28 2004-08-12 E.I. Du Pont De Nemours And Company Insecticides a base de cyano-anthranilamide
JP2004538327A (ja) * 2001-08-13 2004-12-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー アントラニルアミド化合物を被着させることにより特定の害虫を防除する方法
JP2004538328A (ja) * 2001-08-13 2004-12-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 殺節足動物性アントラニルアミド
WO2005077934A1 (fr) * 2004-02-18 2005-08-25 Ishihara Sangyo Kaisha, Ltd. Anthranilamides, procédé pour la production de ceux-ci et agents antiparasitaires contenant ceux-ci
WO2005085234A2 (fr) * 2004-03-03 2005-09-15 Syngenta Participations Ag Nouveaux insecticides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004538327A (ja) * 2001-08-13 2004-12-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー アントラニルアミド化合物を被着させることにより特定の害虫を防除する方法
JP2004538328A (ja) * 2001-08-13 2004-12-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 殺節足動物性アントラニルアミド
WO2004067528A1 (fr) * 2003-01-28 2004-08-12 E.I. Du Pont De Nemours And Company Insecticides a base de cyano-anthranilamide
WO2005077934A1 (fr) * 2004-02-18 2005-08-25 Ishihara Sangyo Kaisha, Ltd. Anthranilamides, procédé pour la production de ceux-ci et agents antiparasitaires contenant ceux-ci
WO2005085234A2 (fr) * 2004-03-03 2005-09-15 Syngenta Participations Ag Nouveaux insecticides

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2482677C2 (ru) * 2008-03-13 2013-05-27 Исихара Сангио Кайся, Лтд. Композиции пестицидов
AU2009224263B2 (en) * 2008-03-13 2014-02-27 Ishihara Sangyo Kaisha, Ltd. Pesticidal compositions
WO2009113712A3 (fr) * 2008-03-13 2010-08-12 Ishihara Sangyo Kaisha, Ltd. Compositions pesticides
WO2009113712A2 (fr) * 2008-03-13 2009-09-17 Ishihara Sangyo Kaisha, Ltd. Compositions pesticides
CN101969775A (zh) * 2008-03-13 2011-02-09 石原产业株式会社 杀虫组合物
US8529926B2 (en) 2008-03-13 2013-09-10 Ishihara Sangyo Kaisha, Ltd. Pesticidal compositions
WO2010010958A3 (fr) * 2008-07-24 2010-09-30 Ishihara Sangyo Kaisha, Ltd. Composition pesticide
WO2010010958A2 (fr) * 2008-07-24 2010-01-28 Ishihara Sangyo Kaisha, Ltd. Composition pesticide
KR101811897B1 (ko) * 2010-04-27 2017-12-22 스미또모 가가꾸 가부시키가이샤 유해 생물 방제 조성물 및 그의 용도
CN102060770A (zh) * 2010-12-27 2011-05-18 浙江工业大学 一种邻甲酰胺基苯甲酰胺类化合物及中间体的制备与应用
CN102617551A (zh) * 2012-03-08 2012-08-01 华东理工大学 含二氟(亚)甲基邻甲酰胺基苯甲酰胺类化合物
WO2015184229A1 (fr) * 2014-05-29 2015-12-03 E. I. Du Pont De Nemours And Company Procede pour la preparation de l'acide 3-methyl-2-nitrobenzoïque par l'oxydation a l'air
JP2017516808A (ja) * 2014-05-29 2017-06-22 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ 空気酸化による３−メチル−２−ニトロ安息香酸の調製プロセス
RU2689126C2 (ru) * 2014-05-29 2019-05-24 ЭфЭмСи Корпорейшн Способ получения 3-метил-2-нитробензойной кислоты посредством окисления воздухом

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