WO2007020877A1 - Composés d’anthranilamide, processus de production idoine, et agent antiparasitaire comprenant lesdits composés - Google Patents

Composés d’anthranilamide, processus de production idoine, et agent antiparasitaire comprenant lesdits composés Download PDF

Info

Publication number
WO2007020877A1
WO2007020877A1 PCT/JP2006/315862 JP2006315862W WO2007020877A1 WO 2007020877 A1 WO2007020877 A1 WO 2007020877A1 JP 2006315862 W JP2006315862 W JP 2006315862W WO 2007020877 A1 WO2007020877 A1 WO 2007020877A1
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
optionally substituted
alkyl
halogen
alkoxy
Prior art date
Application number
PCT/JP2006/315862
Other languages
English (en)
Japanese (ja)
Inventor
Terumasa Komyoji
Toru Koyanagi
Hirohiko Kimura
Masayuki Morita
Tetsuo Yoneda
Toyoshi Tanimura
Kazuhisa Kiriyama
Kenichi Nakamoto
Taku Hamamoto
Akihiro Hisamatsu
Original Assignee
Ishihara Sangyo Kaisha, Ltd.
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 Ishihara Sangyo Kaisha, Ltd. filed Critical Ishihara Sangyo Kaisha, Ltd.
Publication of WO2007020877A1 publication Critical patent/WO2007020877A1/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
    • A01N43/48—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • WO01Z70671 discloses anthranilamide compounds having a certain chemical structure. However, no compound having an alkyl substituted with C3-4 cycloalkyl or a carbonyl substituted with D as a substituent corresponding to A in the following formula (I) is described. .
  • WO03Z16284 discloses a compound in which 2-pyridyl or phenyl is substituted at the 1-position of the pyrazole ring
  • WO04Z67528 discloses a compound in which 2-pyridyl is substituted at the 1-position of the pyrazole ring.
  • the chemical structure is different because 3-pyridyl or 4-pyridyl is substituted at the 1-position of the pyrazole ring of the following formula (I).
  • Patent Document 1 International Publication WO01Z70671
  • Patent Document 2 International Publication WO03Z16284
  • Patent Document 3 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):
  • A is alkyl substituted with Y or carbo substituted with D
  • Q may be substituted with R, 3-pyridyl or R 5 ! , 4-pyridyl
  • R 1 is halogen, alkyl optionally substituted with X, alkenyl optionally substituted with X, alkyl optionally substituted with X, hydroxy, substituted with X Alkoxy, formyl, alkyl carbonyl optionally substituted with X, carboxyl, alkoxy carbonyl optionally substituted with X, alkyl sulfonyl optionally substituted with X, substituted with X Alkylsulfuriel, alkylsulfol optionally substituted with X, optionally substituted with X !, alkylsulfuroxy, optionally substituted with X !, alkylsulfieroxy, X Alkylsulfo-luoxy, which may be substituted with Alkylamino, dialkyla
  • a pest control agent comprising a novel anthranilamido compound of the formula (I) as an active ingredient is
  • each substituent may be the same or different.
  • the position of each substituent may be any position.
  • the number of substituents Y in A is preferably 1.
  • the number of substituents R 5 in Q is preferably 1 to 2.
  • the number of substitutions of halogen as a substituent in X, Y or D is 1 or 2 or more. When 2 or more, each halogen may be the same or different. Also, the substitution position of each halogen is! /.
  • the number of substituents of halogen, alkyl or haloalkyl as a substituent may be 1 or 2 or more. When 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.
  • the halogen in R 2 , R 5 , X, Y or D or the halogen as a substituent includes each atom of fluorine, chlorine, bromine or iodine.
  • the alkyl or alkyl moiety in A, R ⁇ R 2 , R 3 , R 4 , R 5 , X or Y may be either linear or branched. Specific examples thereof include methyl, ethyl, propyl, C, such as isopropyl, n-butyl, tert-butyl, pentyl, hexyl and the like.
  • the alkenyl or alkenyl moiety in R 1 or D may be straight or branched! /, And examples include bulle, 1-probe, allyl, iso-probe. 1-Butyl, 1,3-Butagel, and 1C Hexane.
  • the alkyl or alkyl moiety in R 1 or D may be straight-chain or branched! /, And examples thereof include ethynyl, 2-butulyl, 2-pentyl, 3 —C, such as Hekishur.
  • 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.
  • an alkali metal salt such as a sodium salt or a potassium salt is used.
  • 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 anthracamide compound of the formula (I), its N-oxide, or a salt thereof (hereinafter abbreviated as the present compound) is reacted as follows: [A], [B], [C], [D] And [E] can be produced according to the usual production method of N-oxide or salt.
  • A, Q, R 2 , R 3 , R 4 , m and n are as described above, and Z is a chlorine atom, OH or C aranoloxy.
  • 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 [A] can be carried out in the presence of a solvent, if desired, when Z is a chlorine atom.
  • a solvent if desired, when Z is a chlorine atom.
  • 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, Chlorohonore Halogenated hydrocarbons such as benzene, toluene, xylene; pentane, hexane, heptane, octane, cyclohexane
  • Non-polar hydrocarbons such as acetonitrile, propio-tolyl, ⁇ , ⁇ dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane,
  • the reaction [ ⁇ ] can be carried out usually at 20 to + 60 ° C, preferably 0 to 30 ° C when ⁇ is a chlorine atom, and the reaction time is usually about 1 to 24 hours, preferably 2 It can be about ⁇ 12 hours.
  • reaction [A] can usually be carried out in the presence of a dehydration condensing agent and a solvent when Z is —OH.
  • dehydrating condensing agents examples include carbodiimides such as ⁇ , ⁇ '-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride; , —Carbo-Rubis—1H—Imidazole, phosphoric acid diester, Jetylphosphorus Dart 1,3,5 Triaza 1,2,4,6 Triphosphorin 2,2,4,4,6, 6 Hexachloride, cyanuric chloride, black isobutyl formate, chlorosulfol isocyanate, trifluoroacetic anhydride and the like.
  • carbodiimides such as ⁇ , ⁇ '-dicyclohexylcarbodiimide, 1,3 diisopropylcarbodiimide, 1-ethyl 3- (3 dimethylaminopropyl) carbodiimide hydrochloride
  • 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 , Dichloromethane, Chlorophenol, Carbon tetrachloride, Dichloroethane, Trichloroethane, Dichloroethylene, Halogenated hydrocarbons; Benzene, Toluene, Xylene, Aromatic hydrocarbons; Acetonitrile, Propio-tolyl, ⁇ , ⁇ Polar aprotic solvents such as dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulfolane, ⁇ , ⁇ dimethylacetamide, ⁇ -methylpyrrolidone; ES such as methyl acetate, ethyl acetate, propyl acetate Tells; Ke
  • Reaction [A] can be carried out usually at 20 to + 60 ° C, preferably 0 to 30 ° C when Z is --OH, and the reaction time is usually about 0.5 to 24 hours, preferably 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 alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; trimethylamine, triethylamine, triisopropyl Amines, diisopropylethylamine, pyridine, 4 dimethylaminopyridine, 2,6 dimethylviridine, 4 pyrrolidinopyridine, N-methylmorpholine, ⁇ , ⁇ dimethylamine, ⁇ , ⁇ jettilin, ⁇ -ethynole ⁇ - It is possible to select one or more as appropriate from tertiary amines such as methenorea-phosphorus, 1,8 diazabicyclo [5.4.0] -7 undecene, 1,4 diazabicyclo [2.2.2] octane, etc. it can.
  • the base can be used in an amount of 1 to 5 times mol, preferably 1 to 2.5 times mol, of the compound
  • 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, hexamethylphosphoric triamide, sulfolane, ⁇ , ⁇ dimethylacet
  • the reaction [ ⁇ ] is usually 0 to 120 ° C, preferably 20 to 80 when ⁇ is C alkoxy.
  • the reaction time can be usually about 0.5 to 24 hours, preferably about 1 to 12 hours.
  • A, Q, R ⁇ R 2, R 4, m and n are as defined above.
  • Reaction [B] can usually be carried out 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, and dichloroethylene; aromatic hydrocarbons such as benzene, toluene, and xylene; pentane, hexane, heptane, octane, and cyclohexane Aliphatic hydrocarbons such as: acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, ⁇ , ⁇ -dimethylacetamide,
  • Reaction [B1 can be carried out in the presence of a base when ⁇ is a carbo substituted with D. it can.
  • a base for example, one or more kinds can be appropriately selected from alkali metal hydrides 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 (V).
  • the reaction [B] 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 3 , R 4 , m and n are as described above, Q 1 is 3 pyridyl which may be substituted with or 4 pyridyl which may be substituted with R 5a , and R la is fluorine Atom, chlorine atom, bromine atom, alkyl optionally substituted with X, alkaryl optionally substituted with X, alkyl optionally substituted with X, hydroxy, alkoxy optionally substituted with X , Formyl, alkyl carbonyl optionally substituted with X, carboxyl, alkoxy carb optionally substituted with X, alkyl sulfonyl optionally substituted with X, optionally substituted with X Alkylsulfifer, alkylsulfole optionally substituted with X, alkylsulfoxyloxy optionally substituted with X, alkylsulfieroxy optionally substituted with X, optionally substituted with X Alkylsulf
  • 5a is a fluorine atom, chlorine atom, bromine atom, alkyl optionally substituted with X, alkoxy optionally substituted with X, alkylsulfuryl optionally substituted with X, and optionally substituted with X Alkylsulfuriel, alkylsulfol optionally substituted with X, substituted with X, alkylsulfuroxy, substituted with X, alkylsulfuroxy, substituted with X Alkylsulfo-oxy, amino-containing alkylamino, dialkylamino, formyl, cyano or -toro (X is as described above), and U is a bromine atom or an iodine atom.
  • the metal cyanide in the reaction [C] one or more can be appropriately selected from, for example, copper cyanide, cyanogen zinc, potassium cyanide 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 (1-2).
  • Reaction [C] can usually be carried out in the presence of a solvent.
  • 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; acetonitryl, propio-tolyl, ⁇ , ⁇ -Dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, ⁇ , ⁇ -dimethylacetamide, ⁇ -methylpyrrolidone and other polar aprotic solvents, etc. can do
  • the reaction [C] can be carried out in the presence of a palladium catalyst, if desired.
  • a palladium catalyst for example, one kind or two or more kinds can be appropriately selected from tetrakistriphenylphosphine palladium, bistriphenylphosphine palladium dichloride, and the like.
  • Reaction [C] can be carried out in the presence of a metal iodide, if desired.
  • the metal iodide for example, one or more kinds can be appropriately selected from copper iodide, zinc iodide, potassium iodide and the like.
  • Reaction [C] is usually 0 to 150 ° C, preferably 10 to: LOO ° C.
  • the reaction time is usually about 0.1 to 24 hours, preferably about 0.5 to 12 hours. Can do.
  • [0026] [Chemical 5]
  • the carbon monoxide in the reaction [D] can be used in an amount of 1 to 200 times mol, preferably 1 to 50 times mol for the compound of the formula (1-2).
  • 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 times, preferably 1 to 1.5 times the amount of the compound of the formula (1-2).
  • Reaction [D] can usually be carried out in the presence of a palladium catalyst.
  • a palladium catalyst for example, one 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 may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene and xylene; like pentane, hexane, heptane, octane and cyclohexane.
  • Aliphatic hydrocarbons jetyl ether, butyl ether, tetrahydrofuran, di Ethers such as dioxane and dimethoxyethane; acetonitrile, propio-tolyl, ⁇ , ⁇ — dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, ⁇ , ⁇ dimethylacetamide, ⁇ -methylpyrrolidone
  • polar aprotic solvents can be appropriately selected.
  • Reaction [D] is usually 0 to 150 ° C, preferably 10 to: LOO ° C.
  • the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 12 hours. Can do.
  • R 3, R 4, m and n are as defined above, Q 2 is 4-pyridyl which may be substituted with may be 3-pyridyl or R 5b is substituted with R 5b, R lb Is a fluorine atom, a chlorine atom, a bromine atom, an alkyl which may be substituted with X, an alkyl which may be substituted with X, an alkyl which may be substituted with X, a hydroxy, which may be substituted with X Good alkoxy, alkyl carbo optionally substituted with X, carboxyl, alkoxy carbo optionally substituted with X, alkyl sulf optionally substituted with X, alkyl sulf optionally substituted with X -Alkyl, alkylsulfol optionally substituted with X, alkylsulfuroxy optionally substituted with X, alkylsulferoxy optionally substituted with X, alkyls
  • fluorine-containing agent in the reaction [E] for example, cetylaminosulfur trifluoride, [bis (2-methoxyethyl) monoamino] sulfur trifluoride, xenon fluoride, 2,2-difluoro-1, 3
  • the fluorine-containing agent can be used in an amount of 1 to 10 times mol, preferably 1 to 4 times mol for the compound of formula (1-5).
  • 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, xylene Aromatic hydrocarbons such as: Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, halogenated trichloromethane, dichloroethane, trichloroethane, dichloroethylene; halogenated hydrocarbons;
  • one or more kinds can be appropriately selected from ethers such as butyl ether, tetrahydrofuran, dioxane and dimethoxyethane.
  • the reaction [E] can be carried out under an inert gas atmosphere if desired.
  • the inert gas include nitrogen, helium, and argon.
  • Reaction [E] can usually be carried out at ⁇ 78 to 40 ° C., preferably ⁇ 40 to 25 ° C.
  • the reaction time is usually about 2 to 24 hours, preferably about 5 to 15 hours. Can do.
  • the compound of the formula (II) is a known compound, or can be produced according to known materials.
  • the compound of the formula (II) can be produced, for example, according to the method described in Synthesis, 1980, p.
  • QR 2 and n are as described above, and B is halogen.
  • Halogen includes fluorine, chlorine, bromine and iodine atoms.
  • the compound of formula (VI) is a known compound.
  • the first step of reaction [F] can usually be carried out in the presence of a base and a solvent.
  • the base 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 solvent may be any solvent inert to the reaction.
  • polar aprotic solvents such as sulfolane, ⁇ , ⁇ -dimethylacetamide, and ⁇ -methylbicycloidone can be appropriately selected.
  • the first step of the reaction [F] can be carried out under an inert gas atmosphere if desired.
  • inert gases include nitrogen, helium, and argon.
  • the first step of the reaction [F] can usually be carried out at 0 to 160 ° C, preferably 10 to 130 ° C, and the reaction time is usually about 1 to 72 hours, preferably about 2 to 60 hours. can do.
  • the oxidizing agent in the second step of the reaction [F] includes, for example, alkali metal salts of nitrous acid such as sodium chlorite, strong chlorite, sodium bromate; permanganic acid
  • alkali metal salts or ammonium salts of permanganate such as potassium, barium permanganate, and ammonium permanganate can be appropriately selected.
  • the oxidizing agent can be used in an amount of 1 to 10 times mol, preferably 2 to 8 times mol, of the compound of formula (VII).
  • the second step of the reaction [F] can be usually performed in the presence of a solvent.
  • a solvent Any solvent may be used as long as it is inert to the reaction.
  • halogenated hydrocarbons such as form and dichloroethylene; water and the like can be appropriately selected.
  • the second step of reaction [F] can be carried out in the presence of a pH adjusting agent if desired.
  • a pH adjusting agent examples include sodium acetate and sodium dihydrogen phosphate dihydrate.
  • the second step of reaction [F] can usually be carried out at ⁇ 20 to 130 ° C., preferably ⁇ 5 to 110 ° C., and the reaction time is usually about 1 to 24 hours, preferably 2 to 15 It can be about hours.
  • the compound of the above formula (IV) can be produced according to a known compound or a known document.
  • the compound of the formula (IV) can be prepared by the method described in Org. Prep. Proceed. Int., 1993, 25, page 589, the method described in schemes 8 to 10 in WO03Z24222, or the like. Can be manufactured.
  • the compound of the formula (V) includes a novel compound.
  • the compound can be produced by the Gabriel method, but those in which R 4 is a hydrogen atom can be produced, for example, according to the following reaction [G].
  • 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.
  • the sulfonate residue include C alkyl such as methyl and ethyl;
  • T is halogen or —OSO G
  • M is sodium or
  • Any solvent may be used as long as it is inert to the reaction.
  • jet ether butyl ether, tetrahydrofuran, dioxane, dimethoxy ester.
  • Ethers such as tan; aromatic hydrocarbons such as benzene, toluene, xylene; acetonitrile, propio-tolyl, ⁇ , ⁇ -dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric triamide, sulfolane, ⁇ , Polar aprotic solvents such as ⁇ -dimethylacetamide and ⁇ -methylpyrrolidone; one or more selected from alcohols such as methanol, ethanol, propanol, normal butanol, and tertiary butanol can do.
  • ⁇ 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 [G] is a force that can usually be performed according to the Mitsunobu method when T is —OH and M is a hydrogen atom.
  • a dialkylazo It can be carried out using dicarboxylate and triphenylphosphine.
  • the dialkylazodicarboxylate and triphenylphosphine can be used in an equimolar amount with respect to the compound of formula (VIII).
  • the dialkylazodicarboxylate is a force that can usually be performed according to the Mitsunobu method when T is —OH and M is a hydrogen atom.
  • Examples thereof include jetylazodicarboxylate and diisopropylazodicarboxylate.
  • 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, dichloroethane, trichloroethane, and dichloroethylene
  • aromatic hydrocarbons such as benzene, toluene, and xylene can be appropriately selected.
  • the first step of the reaction [G] 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.
  • the reaction time is usually about 0.5 to 24 hours, preferably about 1 to 16 hours.
  • the second step of the reaction [G] can be usually performed by decomposing the compound of the formula (X) with hydrazine in the presence of a solvent.
  • the hydrazine is usually against the compound of formula (X).
  • 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 [G] 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 pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents parasitic on animals, that is, animals. It is particularly useful as a parasite control agent.
  • Pesticides for agricultural and horticultural use include, for example, power useful as insecticides, acaricides, nematicides, and soil-killing insecticides.
  • Plant parasitic mites such as apple hada, chiyanokorida, mandarin orange, mite, etc .
  • 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 .; Bataga, Azuki beetle, Kokunosutomodoki, Goomushimodashi Stored pests such as moss; clothing, house pests such as Iga, Himekatsubushimushi, termites, etc .; It is effective for controlling ticks; Among them, the agricultural and horticultural pest 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 pest control agent containing the compound of the present invention is also effective in controlling various pests resistant to 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, it is possible to treat soil harmful insects, ticks, and the like by treating the soil with an agricultural and horticultural pesticide containing the compound of the present invention.
  • it can also control pests on the foliage.
  • Another desirable aspect of the pest control agent containing the compound of the present invention is that the 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 obtained by mixing the compound and various agricultural adjuvants. , Oily suspension, water solvent, emulsion, liquid, paste, aerosol, microspray, etc. Any formulation used in the field can be used.
  • 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-pyrrolidone, alcohol and other solvents; fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, Alkyl diglycol ether Sulfates, alcohol sulfates, alkyl sulfonates, alkyl aryl sulfonates, aryl sulfonates, lignite sulfonates, alkyl diphen
  • 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.
  • they can be appropriately selected from those known in the art, for example, extenders, thickeners, anti-settling agents, antifreeze agents, dispersion stabilizers, phytotoxicity reductions.
  • Various commonly used adjuvants such as agents and fungicides can also be used.
  • the compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10.
  • the application of agricultural and horticultural pesticides containing the compounds of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation, application time, application location, pest type and occurrence, etc.
  • the active ingredient concentration is ⁇ 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.
  • the pest control agent containing this invention compound The application of the pest control agent for agricultural and horticultural use, which is another desirable embodiment of the above, 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.
  • the agricultural and horticultural pesticide containing the compound of the present invention can be mixed or used in combination 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 between the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be defined 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, for example, profenofos ( Profenofos, Cyclonorevos, Dichlorvos, Fenamithion, Fenitrothion, EPN, Diazinon, Chlorpyrif os-methyl, Acephate, Prothiofos, Phostiazate Fosth iazate), Phosphocarb, Cadusafos, Dislfoton, Chlorpyrifos, Demeton-S-methyl, Dimethoate, Methamidophos, AKD- Organophosphate compounds such as Parathion;
  • profenofos Profenofos, Cyclonorevos, Dichlorvos, Fenamithion, Fenitrothion, EPN, Diazinon, Chlorpyrif os-methyl, Acephate, Prothiof
  • Nereistoxin derivatives such as Cartap, Thiocyclam, Bensultap;
  • Organochlorine compounds such as Dicofol, Tetradifon, Endosulfan;
  • Organometallic compounds such as Fenbutatin Oxide
  • Fenvalerate Penoremethrin (Permethrin), Cypermethrin (Cypermethr in), Deltamethrin, Deltahalothrin (Cyhalothrin), Tefluthrin, Etofenprox, Fenpropathrin, Fenpropathrin Pyrethroid compounds such as (Bifenthrin);
  • Pyridazinone compounds such as Pyridaben
  • Fenpyroximate Fipronil, Tebu fenpyrad, Ethiprole, Tolfenpyrad, Acetoprole, Pyrafluprole, Pyriprozole, Pyriprole
  • Neo-cotinoids such as Imidacloprid, Nitenpyram, Acetamiprid, Thiacloprid, Thiamethoxam, Clothia nidin, Dinoteforan;
  • Hydrazine compounds such as Tebufenozide, Methoxyfenozide, Chromafenozide, and Halofenozide;
  • Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazine compounds, and other compounds include Flonicamid, Buprofezin, Hexythiazox, Amitraz ( Amitraz), Chlordimeform (Ch lordimeform), Silafrofen (Silafluofen), Triazamate, Pymetrozine, Pyrimidifen, Chlorfenapyr, Indquinocolyl, Indoxaoc Etoxazole), cyromazine, 1,3-dichloropropene, 1,3-dichloropropene, diafenthiuron, Benclothiaz, Flufenerim, pyridylyl, spirodiclo Firo (Spirodiclofen), Bifenazate (Bifenazate) Spiromesifen, Spirotetramat, Propargite, Clofentezine, Fluacrypyrim, Flubendiamide, DPX-E
  • microbial agents such as BT agents, entomopathogenic virus agents, entomopathogenic fungi agents, nematode pathogenic fungi agents, etc .; Avenoremectin (Avermectin), Emamectin- Benzoate, Milbemectin ( Milbemectin), Spinosad, Ivermectin, Antibiotics such as pimectin (Lepimectin) or semi-synthetic substances thereof; natural products such as azadirachtin and rotenone can also be mixed and used together.
  • Dithiocarbamate compounds such as Maneb, Zineb, Mancozeb, Polycarba mate, Propineb;
  • Organochlorine compounds such as Fthalide, Chlorothalonil, Quintozene;
  • Imidazole compounds such as Benomyl, Thiophanate-Methyl, Carbendazim, Cyazofamid;
  • Cyanoacetamide compounds such as Cymoxanil
  • Phenolic compounds such as Metalaxyl, Oxadixyl, Offorace, Benalaxyl, Furalaxyl, Cyproforam;
  • Sulfenic acid compounds such as dichlofluanid
  • Copper-based compounds such as cupric hydroxide and organic copper (Oxine Copper); Isoxazole compounds such as hydroxyisoxazole; Fosety ⁇ Al, Torclofos-Methyl, S-Benzyl ⁇ , ⁇ -diisopropylphosphorothioate, O-Ethyl S, S—Organic phosphorus compounds such as diphenylphosphlodithioate and aluminium hydrogen phosphonate;
  • N-halogenoalkyl compounds such as Captan, Captafol, Folpet;
  • Dicarboximide compounds such as procymidone, Iprodione, Vinclozolin;
  • Benth anilide compounds such as Flutol (Flut 0 lanil), Meprol (Mepronil), Zoxamide;
  • Piperazine compounds such as Triforine
  • Pyridine compounds such as Pyrifenox
  • Carbinol compounds such as Fenarimol and Flutriafol Piperidine compounds such as Fenpropidine;
  • Morpholine compounds such as Fenpropimorph
  • Organotin compounds such as Fentin Hydroxide and Fentin Acetate
  • Urea-based compounds such as Pencycuron
  • Synamic acid compounds such as Dimethomorph
  • Fercarbamate compounds such as Dietophencarb
  • Cyanpyrrole compounds such as Fludioxonil and Fenpiclonil
  • Oxazolidinone compounds such as Azoxystrobin, Kresoxim-Methyl, Metominofen, Trifloxystrobin, Picoxystrobin (Picoxys Famoxadone); Thiazole carboxamide compounds such as ethaboxam; silylamide compounds such as silthiopham;
  • Aminoacid amide carbamate compounds such as Iprovalicarb; Imidazolidine compounds such as Fenamidone;
  • Hydoxyxanilide compounds such as fenhexamid
  • Benzenesulfonamide compounds such as Flusulfamide; Atolaquinone compounds; Crotonic acid compounds; Antibiotics and other compounds such as I so prothiolane, Tricyclazole, Pyroquilon, Dichromemidine ( Diclomezine), Purobe mystery one / LES (Probenazole), quinoxyfen (Quinoxyf en), Puropamokanorebu hydrochloride (Propamocarb hydrochloride), spiroxamine (Spiroxami n e), chloropicrin (chloropicrin), dazomet (dazomet), meta beam sodium salt ( Metam- sodi um);
  • pesticides that can be mixed or used in combination with the compounds of the present invention include, for example, active ingredients of herbicides such as those described in the Farm Chemicals Handbook (2002 edition), particularly those of soil treatment type. 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 that parasitize the heart, liver, blood vessels, subcutaneous, lymphatic thread, and the like, and 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, Rhipicephalus sanguineus, Phytophthora, eu (Haemaphvsalis longicorni s), Kitani tick (Haemaphvsalis flava), burdock mite ph , Chair power zima, 'e (Haemaphvsalis concinna), yamato chimata-(Haemaphvsalis ja ⁇ onica), Haemaphvsalis kitaokai, Haemaphvsalis ias, tick (Ixodes ovatus) Ixodes nipponensis), sur zuemata, ii (Ixodes persulcatus), Takasago Kiramata (Amblvomma testudinarium) Ticks, such as the genius Tematani (Haemaphvsalis megaspinosa), Acarid tick (
  • fleas examples include ectoparasite worms belonging to the order Flea (Siphonaotera), and more specifically fleas belonging to the family Flea (Pulicidae), Nagano (CerateDhyllus), etc. .
  • Examples of fleas belonging to the family Fleas include: Flea (Ctenoce Dhalides canis), Cono (Ctenocephalides felis), Human flea (Pulex irritans), -Echidnoph aga gallinacea, Xenopsvlla cheopis, Examples include fleas (Leptopsvl la segnis), yosoku tsuno ⁇ nozuno (Nosopsyllus fasciatus), yamanoshino (Monopsvll us mik), etc.
  • animal parasite control agents containing the compounds of the present invention include: It is effective for controlling fleas belonging to the family Flea family, especially cynos and cat fleas.
  • 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 Thmetgebu Diptera pests.
  • endophytic organisms include nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms; , Persimmon tapeworm, multi-headed tapeworm, single Tapeworms, tapeworms such as polychaete, Japanese schistosomiasis, fluke such as liver cirrhosis; protozoa such as coccidium, malaria parasite, intestinal granulocyst, toxoplasma, cryptosporidium Etc.
  • nematodes such as lungworms, bench beetles, tuberous worms, gastric parasites, roundworms, and filamentous worms
  • Persimmon tapeworm multi-headed tapeworm, single Tapeworms, tapeworms such as polychaete, Japanese schistosomiasis, fluke such as liver cirrhosis
  • protozoa such as coccidium, malaria parasite, intestinal granulocyst, to
  • Examples of host animals include various pet animals, livestock, poultry, and the like, and more specifically, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (for example, , Pigeons, omme, nine-birds, wild birds, parakeets, pine pine, canary, etc.), sushi, horses, butter, hidge, ducks, etc.
  • 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, liquid agents, emulsions, aquatic compounds with appropriate adjuvants. It can also be formulated and used in various forms such as a suspension and 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, ⁇ -methyl-2-pyrrolidone, kerosene, triacetin, Methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol nore, butinoresin glycol nore, ethylene glycol nole monomethylenoatenore, ethylene glycolenolemonochinenoatenoate, Diethylene Solvents such as ricono-remonomethino-reinotenole, diethyleneglycolenorenoremanolebutenoreatenore, dipropyleneglycololemonomethinoreate, dipropyleneglycolnormalbutylether; butylhydroxyl-sol, butylhydroxyto
  • one or more kinds can be appropriately selected and used.
  • auxiliary agents they can be appropriately selected from those known in the field, and further, the various auxiliary agents used in the above-mentioned agricultural and horticultural fields are appropriately selected. Can also be used.
  • the compounding ratio of the compound of the present invention and 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.
  • 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 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 usually O.Olmg to: L00g 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 by controlling animal parasitic pests as described above, it may be possible to prevent or treat various diseases of host animals caused by them.
  • the present invention also includes a prophylactic or therapeutic agent for parasite-derived animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasite-derived animal diseases. included.
  • the compound of the present invention when used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, antiphlogistics, 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. In this case, the effect may be even better.
  • 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 organic layer was gradually added dropwise to a mixed solution of 32 g of sodium bisulfite and 400 ml of water at 20 ° C or lower. After stirring for 15 minutes at the same temperature, the organic layer was extracted. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 1— (3,5 dichloro-4-pyridyl) 3 (trifluoromethyl) 1H pyrazol-5-carboxylic acid with a melting point of 1 27.9 ° C. 4.7g was obtained.
  • 0.3 ml of methanesulfuryl chloride was gradually added dropwise to a mixed solution of 1.0 g of 5-strong rubonic acid, 0.42 ml of pyridine and 20 ml of acetonitrile in a nitrogen stream at 0 ° C. After completion of the dropwise addition, stirring was continued for 15 minutes at the same temperature, to which 0.57 g of 2 amino-5 black mouth 3-methylbenzoic acid was added, and then 0.87 ml of pyridine was added. After stirring at 0 ° C for 15 minutes, 0.3 ml of methanesulfonyl chloride was added, and the mixture was allowed to react while gradually returning the solution temperature to room temperature.
  • the filtrate was washed with saturated aqueous sodium hydrogen carbonate solution and saturated Japanese brine, dried over anhydrous magnesium sulfate.
  • the organic layer was gradually added dropwise to a mixed solution of 30 g of sodium bisulfite and 200 ml of water at 20 ° C or lower. After stirring for 15 minutes at the same temperature, the organic layer was extracted. After drying over sodium sulfate, the solvent is distilled off under reduced pressure, melting point 130—135 ° C 1 — (4 Kuroguchi 1-3 pyridyl) 3 (trifluoromethyl) -1H-pyrazole 5 carboxylic acid 1.5 g Got.
  • the NMR spectrum data of this product are as follows.
  • Table 1 representative examples of the compounds of the present invention represented by the formula (I) are shown in Table 1, and their physical properties are shown in Table 2. These compounds can be synthesized based on the above synthesis examples or various production methods of the above-described compounds of the present invention.
  • No. indicates the compound No., and the position indicates the position at which pyrazole is bonded to the carbocycle.
  • A1 is -CH- [c-Pr]
  • A2 is -CH (Me)-[c-Pr]
  • A3 is -C
  • F and A15 each represent —CO—CH ⁇ CH.
  • Me is methyl group
  • c-Pr is
  • a chloropropyl group, c-Bu represents a cyclobutyl group, and Py represents a pyridyl group.
  • c-Pr (2-Me) is a cyclopropyl group substituted with a methyl group at the 2-position
  • 4-Py (3-Cl, 5-Cl) is A 4-pyridyl group substituted with a chlorine atom at the 3-position and 5-position of the pyridyl group is shown, and other similar descriptions also apply 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.
  • a wet filter paper was laid on a petri dish with a diameter of 9 cm, and an air-dried piece of cabbage was placed on top of it.
  • the mortality was determined and the mortality rate was calculated by the following formula. Abnormal insects were also considered dead.
  • Compound Nos Compound Nos.
  • Death rate (%) (Number of dead insects Z Number of dead insects) X loo
  • Test Example 2 Effect test on silver leaf whitefly
  • Silver leaf whitefly adults were allowed to lay eggs for about 8 to 24 hours in a pot-planted cucumber with one leaf left and the other leaves removed. After that, it was left in a constant temperature room at 25 ° C for 7-10 days. After investigating the number of hatched larvae, the chemical solution prepared so that the concentration of the compound of the present invention was 50 ppm was sprayed at a ratio of about 3 ml Z strain and air-dried. After the treatment, the sample was left in a constant temperature room at 25 ° C for 10 to 14 days. Then, the number of old larvae and the number of pupae was examined, and the control value was calculated by the following formula. Compound No. 1, 9, 12, 13, 22, 34, 40, 121, 133, 136, 142, and 144 were determined to have a control value of 50 ppm. High control effect was shown.
  • Control value (%) (1— ((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
  • a filter paper was placed in a glass petri dish having a diameter of 9 cm, and treated with 1 ml of a chemical solution prepared so that the concentration of the compound of the present invention was 500 ppm. After that, we released 10 termite worker ants and 1 soldier ant, covered them, and left them in a constant temperature room at 25 ° C. Six days after the treatment, the number of ant mortality was investigated, and the death rate was calculated using the following formula. Abnormal insects were also considered dead. When the mortality was determined for the compounds No. 1, 6 and 8, all the compounds showed a high control effect of 80% or more.
  • 0.5 ml of an acetone solution of the compound of the present invention prepared at 5.3 ppm is dropped into a glass tube (inner diameter 2.6 cm, bottom area 5.3 cm 2 , height 12 cm) having a smooth bottom surface.
  • Acetone is evaporated at room temperature to form a dry film containing the compound of the present invention on the bottom surface.
  • the above is uniformly mixed to form a powder.
  • a 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 is uniformly mixed and pulverized to obtain an aqueous suspension.
  • the above ingredients are mixed uniformly to form a solution.
  • the novel anthranilamide compound of the present invention has a very low control amount and has a very high control effect against pests. For example, it controls various pests that are problematic in the field of agriculture and horticulture and pests that are parasitic on animals It can be widely used as a pest control agent. It should be noted that the entire contents of the specification, claims, drawings and abstract of Japanese Patent Application No. 2005-234214 filed on August 12, 2005 are cited here as disclosure of the specification of the present invention. Incorporate.

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Public Health (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention a trait à un nouvel agent antiparasitaire. L’invention concerne aussi : un composé d’anthranilamide représenté par la formule (I) : (I) (selon laquelle A est un alkyle à substitution Y ou un carbonyle à substitution D ; Q est 3-pyridyle facultativement substitué par R5 ou 4-pyridyle facultativement substitué par R5 ; R1 est halogéno, alkyle facultativement substitué par X, etc. ; R2 et R5 sont chacun halogéno, alkyle facultativement substitué par X etc. ; R3 et R4 sont chacun un hydrogène ou un alkyle ; X est halogéno, alkoxy halogéné facultativement, etc. ; Y est cycloalkyle C3-4 etc. ; D est alcényle, etc. ; m est un entier compris entre 0 et 4 ; et n est égal à 1 ou 2) ; un N-oxyde du composé ; et un sel du composé.
PCT/JP2006/315862 2005-08-12 2006-08-10 Composés d’anthranilamide, processus de production idoine, et agent antiparasitaire comprenant lesdits composés WO2007020877A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005234214 2005-08-12
JP2005-234214 2005-08-12

Publications (1)

Publication Number Publication Date
WO2007020877A1 true WO2007020877A1 (fr) 2007-02-22

Family

ID=37757539

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2006/315862 WO2007020877A1 (fr) 2005-08-12 2006-08-10 Composés d’anthranilamide, processus de production idoine, et agent antiparasitaire comprenant lesdits composés

Country Status (1)

Country Link
WO (1) WO2007020877A1 (fr)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007144100A1 (fr) 2006-06-13 2007-12-21 Bayer Cropscience Ag Dérivé de diamide d'acide anthranilique avec substituants hétéroaromatiques et hétérocycliques
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
WO2011098408A2 (fr) 2010-02-09 2011-08-18 Bayer Cropscience Ag Dérivés d'acide anthranilique à substitution hydrazine
WO2011128329A1 (fr) 2010-04-16 2011-10-20 Bayer Cropscience Ag Amides d'acide anthranilique substitués par des triazoles utilisables comme pesticides
WO2011157653A1 (fr) 2010-06-15 2011-12-22 Bayer Cropscience Ag Dérivés d'acide anthranilique
WO2011157654A1 (fr) 2010-06-15 2011-12-22 Bayer Cropscience Ag Dérivés de diamide d'acide anthranilique
WO2011157663A1 (fr) 2010-06-15 2011-12-22 Bayer Cropscience Ag Nouveaux dérivés arylamide ortho-substitués
WO2011157651A1 (fr) 2010-06-15 2011-12-22 Bayer Cropscience Ag Dérivés de diamide d'acide anthranilique à chaînes latérales cycliques
WO2012004208A1 (fr) 2010-07-09 2012-01-12 Bayer Cropscience Ag Dérivés de diamide d'acide anthranilique utilisés comme pesticides
EP2484676A2 (fr) 2008-12-18 2012-08-08 Bayer CropScience AG Amides d'acide anthranilique substitués au tétrazole en tant que pesticides
WO2013024005A1 (fr) * 2011-08-12 2013-02-21 Basf Se Composés anthranilamides et leur utilisation comme pesticides
EP2606732A1 (fr) 2011-12-19 2013-06-26 Bayer CropScience AG Utilisation de dérivés de diamide anthranilique avec des substituants hétéro-aromatiques et hétérocycliques en combinaison avec un agent de contrôle biologique
WO2013092519A1 (fr) 2011-12-19 2013-06-27 Bayer Cropscience Ag Utilisation de dérivés de diamide d'acide anthranilique pour lutter contre les organismes nuisibles dans des cultures transgéniques
CN103889955A (zh) * 2011-08-12 2014-06-25 巴斯夫欧洲公司 N-硫代邻氨基苯甲酰胺化合物及其作为农药的用途
WO2014135588A1 (fr) * 2013-03-06 2014-09-12 Bayer Cropscience Ag Diamides d'acide anthranilique substitués par alcoximino, servant de pesticides
US8932613B2 (en) 2007-07-30 2015-01-13 E I Du Pont De Nemours And Company Ectoparasite control method
WO2019123195A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Pyrazolopyridine-diamides, leur utilisation en tant qu'insecticide et leurs procédés de préparation
WO2019123194A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation
WO2019150220A1 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation
US12024510B2 (en) 2017-12-20 2024-07-02 Pi Industries Ltd. Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003528070A (ja) * 2000-03-22 2003-09-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 殺虫性アントラニルアミド類
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
JP2005502716A (ja) * 2001-09-21 2005-01-27 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節足動物殺滅剤処理
JP2005503384A (ja) * 2001-08-16 2005-02-03 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 無脊椎有害生物の防除用の置換アントラニルアミド

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003528070A (ja) * 2000-03-22 2003-09-24 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 殺虫性アントラニルアミド類
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
JP2005503384A (ja) * 2001-08-16 2005-02-03 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 無脊椎有害生物の防除用の置換アントラニルアミド
JP2005502716A (ja) * 2001-09-21 2005-01-27 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節足動物殺滅剤処理
WO2004067528A1 (fr) * 2003-01-28 2004-08-12 E.I. Du Pont De Nemours And Company Insecticides a base de cyano-anthranilamide

Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8101550B2 (en) 2006-06-13 2012-01-24 Bayer Cropscience Ag Anthranilic acid diamide derivative with hetero-aromatic and hetero-cyclic substituents
US8946236B2 (en) 2006-06-13 2015-02-03 Bayer Cropscience Ag Anthranilic acid diamide derivative with hetero-aromatic and hetero-cyclic substituents
US8536092B2 (en) 2006-06-13 2013-09-17 Bayer Cropscience Ag Anthranilic acid diamide derivative with hetero-aromatic and hetero-cyclic substituents
WO2007144100A1 (fr) 2006-06-13 2007-12-21 Bayer Cropscience Ag Dérivé de diamide d'acide anthranilique avec substituants hétéroaromatiques et hétérocycliques
US8932613B2 (en) 2007-07-30 2015-01-13 E I Du Pont De Nemours And Company Ectoparasite control method
US8529926B2 (en) 2008-03-13 2013-09-10 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
WO2010010958A2 (fr) * 2008-07-24 2010-01-28 Ishihara Sangyo Kaisha, Ltd. Composition pesticide
WO2010010958A3 (fr) * 2008-07-24 2010-09-30 Ishihara Sangyo Kaisha, Ltd. Composition pesticide
US8324390B2 (en) 2008-12-18 2012-12-04 Bayer Cropscience Ag Tetrazole-substituted anthranilamides as pesticides
EP2484676A2 (fr) 2008-12-18 2012-08-08 Bayer CropScience AG Amides d'acide anthranilique substitués au tétrazole en tant que pesticides
US8410106B2 (en) 2010-02-09 2013-04-02 Bayer Cropscience Ag Hydrazine-substituted anthranilic acid derivatives
WO2011098408A2 (fr) 2010-02-09 2011-08-18 Bayer Cropscience Ag Dérivés d'acide anthranilique à substitution hydrazine
US8536202B2 (en) 2010-04-16 2013-09-17 Bayer Cropscience Ag Triazole-substituted anthranilamides as pesticides
TWI486124B (zh) * 2010-04-16 2015-06-01 Bayer Cropscience Ag 作為除害劑之經三唑－取代的鄰胺基苯甲醯胺類
WO2011128329A1 (fr) 2010-04-16 2011-10-20 Bayer Cropscience Ag Amides d'acide anthranilique substitués par des triazoles utilisables comme pesticides
US8980886B2 (en) 2010-06-15 2015-03-17 Bayer Cropscience Ag Anthranilic acid derivatives
WO2011157651A1 (fr) 2010-06-15 2011-12-22 Bayer Cropscience Ag Dérivés de diamide d'acide anthranilique à chaînes latérales cycliques
WO2011157663A1 (fr) 2010-06-15 2011-12-22 Bayer Cropscience Ag Nouveaux dérivés arylamide ortho-substitués
US8791143B2 (en) 2010-06-15 2014-07-29 Bayer Cropscience Ag Anthranilic diamide derivatives having cyclic side-chains
WO2011157654A1 (fr) 2010-06-15 2011-12-22 Bayer Cropscience Ag Dérivés de diamide d'acide anthranilique
US8658800B2 (en) 2010-06-15 2014-02-25 Bayer Cropscience Ag Ortho-substituted arylamide derivatives
WO2011157653A1 (fr) 2010-06-15 2011-12-22 Bayer Cropscience Ag Dérivés d'acide anthranilique
US8791139B2 (en) 2010-06-15 2014-07-29 Bayer Cropscience Ag Anthranilic diamide derivatives
US9790202B2 (en) 2010-07-09 2017-10-17 Bayer Intellectual Property Gmbh Anthranilamide derivatives as pesticides
WO2012004208A1 (fr) 2010-07-09 2012-01-12 Bayer Cropscience Ag Dérivés de diamide d'acide anthranilique utilisés comme pesticides
CN103842342A (zh) * 2011-08-12 2014-06-04 巴斯夫欧洲公司 邻氨基苯甲酰胺化合物及其作为农药的用途
WO2013024005A1 (fr) * 2011-08-12 2013-02-21 Basf Se Composés anthranilamides et leur utilisation comme pesticides
CN103889955A (zh) * 2011-08-12 2014-06-25 巴斯夫欧洲公司 N-硫代邻氨基苯甲酰胺化合物及其作为农药的用途
WO2013092516A1 (fr) 2011-12-19 2013-06-27 Bayer Intellectual Property Gmbh Utilisation de dérivés de diamide anthranilique avec des substituants hétéroaromatiques et hétérocycliques en combinaison avec un agent de contrôle biologique
EP2606732A1 (fr) 2011-12-19 2013-06-26 Bayer CropScience AG Utilisation de dérivés de diamide anthranilique avec des substituants hétéro-aromatiques et hétérocycliques en combinaison avec un agent de contrôle biologique
US9414595B2 (en) 2011-12-19 2016-08-16 Bayer Cropscience Ag Use of anthranilic acid diamide derivatives for pest control in transgenic crops
US9572342B2 (en) 2011-12-19 2017-02-21 Bayer Intellectual Property Gmbh Use of an anthranilic diamide derivatives with heteroaromatic and heterocyclic substituents in combination with a biologicalcontrol agent
WO2013092519A1 (fr) 2011-12-19 2013-06-27 Bayer Cropscience Ag Utilisation de dérivés de diamide d'acide anthranilique pour lutter contre les organismes nuisibles dans des cultures transgéniques
US9854802B2 (en) 2011-12-19 2018-01-02 Bayer Intellectual Property Gmbh Use of an anthranilic diamide derivatives with heteroaromatic and heterocyclic substituents in combination with a biological control agent
WO2014135588A1 (fr) * 2013-03-06 2014-09-12 Bayer Cropscience Ag Diamides d'acide anthranilique substitués par alcoximino, servant de pesticides
JP2016512192A (ja) * 2013-03-06 2016-04-25 バイエル・クロップサイエンス・アクチェンゲゼルシャフト 殺害虫剤としてのアルコキシイミノ置換アントラニル酸ジアミド類
US9609868B2 (en) 2013-03-06 2017-04-04 Bayer Cropscience Ag Alkoximino-substituted anthranilic acid diamides as pesticides
WO2019123195A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Pyrazolopyridine-diamides, leur utilisation en tant qu'insecticide et leurs procédés de préparation
WO2019123194A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation
US12024510B2 (en) 2017-12-20 2024-07-02 Pi Industries Ltd. Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same
WO2019150220A1 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation

Similar Documents

Publication Publication Date Title
WO2007020877A1 (fr) Composés d’anthranilamide, processus de production idoine, et agent antiparasitaire comprenant lesdits composés
JP4848391B2 (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
JP4150379B2 (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
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
US20100179172A1 (en) N-phenyl-methanamine derivative and pesticide containing it
JP2003176258A (ja) 酸アミド誘導体、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
WO2006080311A1 (fr) Composé de type anthranilamide, méthode de synthèse dudit composé et agent pesticide contenant ledit composé
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
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
WO2016068301A1 (fr) Agent de lutte contre les parasites
WO2011074677A1 (fr) Dérivé d'imidazopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nuisibles le comprenant
JP2007070346A (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
WO2015025960A1 (fr) Agent de lutte contre les organismes nocifs
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
JP2006001914A (ja) ピリミジン系化合物、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
JP2006232814A (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
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
WO2006118267A1 (fr) Composé de type anthranylamide, méthode de synthèse dudit composé et agent pesticide contenant ledit composé
WO2010018853A1 (fr) Dérivé pyridyle-triazolopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nocifs le comprenant
TWI597267B (zh) 害蟲防治劑
WO2017159618A1 (fr) Agent de lutte contre les animaux nuisibles
JP2007277206A (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
JP2005097228A (ja) ハロアルケン系化合物、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

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06782648

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP