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WO2012029968A1 - Dérivé de benzamide ou son sel, et insecticide, miticide, nématicide ou pesticide du sol contenant celui-ci - Google Patents

Dérivé de benzamide ou son sel, et insecticide, miticide, nématicide ou pesticide du sol contenant celui-ci Download PDF

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Publication number
WO2012029968A1
WO2012029968A1 PCT/JP2011/070090 JP2011070090W WO2012029968A1 WO 2012029968 A1 WO2012029968 A1 WO 2012029968A1 JP 2011070090 W JP2011070090 W JP 2011070090W WO 2012029968 A1 WO2012029968 A1 WO 2012029968A1
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Prior art keywords
salt
benzamide derivative
alkyl
compounds
compound
Prior art date
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Ceased
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PCT/JP2011/070090
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English (en)
Inventor
Tetsuo Yoneda
Kazuhisa Kiriyama
Taku Hamamoto
Tatsuya Kani
Tatsuya Shimada
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Ishihara Sangyo Kaisha Ltd
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Ishihara Sangyo Kaisha Ltd
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Publication of WO2012029968A1 publication Critical patent/WO2012029968A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to a benzamide derivative or its salt, and an insecticide, miticide, nematicide or soil pesticide containing it as an active ingredient.
  • Patent Document 1 discloses that a specific benzamide derivative is useful as a herbicide. However, it does not disclose use of the benzamide derivative as an insecticide, miticide, nematicide or soil pesticide. Further, it does not specifically disclose the benzamide derivative represented by the formula (I) given hereinafter.
  • each of Patent Documents 2 and 3 discloses use of a benzamide derivative having a specific chemical structure as a nematicide. However, such a compound is different from the compound of the present invention in the structure.
  • Patent Document 1 WO 2001/091558
  • Patent Document 2 US Patent No. 4,840,969
  • Patent Document 3 EP 323637 B1 DISCLOSURE OF INVENTION
  • the present inventors have conducted various studies on benzamide derivatives in an effort to find a superior insecticide, miticide, nematicide or soil pesticide. As a result, they have found that the benzamide derivative represented by the formula (I) below has a very high controlling effect particularly against nematodes at a low dose and at the same time has safety to crop plants, natural enemies of insects, etc. or mammals, and have accomplished the present invention.
  • the present invention relates to a benzamide derivative represented by the formula (I) or its salt:
  • R 1 is a hydrogen atom or C1.3 alkyl
  • R 2 is C 2- 8 alkyl or C3-8 cycloalkyl
  • the present invention relates to an insecticide, miticide, nematicide or soil pesticide containing the benzamide derivative of the above formula (I) or its salt as an active ingredient, and a method for controlling insects, mites, nematodes or soil pests, which comprises applying it.
  • An insecticide, miticide, nematicide or soil pesticide containing the benzamide derivative of the above formula (I) or its salt as an active ingredient has a very high controlling effect against insects, mites, nematodes or soil pests at a low dose.
  • the alkyl in the formula (I) may be linear or branched.
  • Ci-e alkyl such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl or octyl may be mentioned.
  • C3-8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl may, for example, be mentioned.
  • the salt of the benzamide derivative of the above formula (I) includes all kinds so long as they are acceptable in this technical field.
  • an ammonium salt such as a dimethylammonium salt or a triethylammonium salt
  • an inorganic acid salt such as a hydrochloride, a perchlorate, a sulfate or a nitrate
  • an organic acid salt such as an acetate or a methanesulfonate
  • the benzamide derivative of the above formula (I) may have isomers, and such isomers and mixtures thereof are both included in the present invention.
  • the isomer of the benzamide derivative of the above formula (I) may, for example, be a
  • stereoisomer such as an enantiomer or a diastereomer, and among them, it is preferably an enantiomer wherein the compound of the formula (I) is a compound having R and R 2 which are different from each other, and represented by the formula
  • R 1 a is d -3 alkyl
  • R 2 a is C 2 -8 alkyl or C 3 -e cycloalkyl
  • R 1 a and R 2 a are different from each other
  • the methine carbon to which R a and R 2 a are bonded is the chiral center.
  • the enantiomer may be the R-enantiomer or the S-enantiomer, and the S-enantiomer is preferred.
  • isomers are in the form of a mixture, unless otherwise specified.
  • various isomers other than those mentioned above may be included within the scope of the common knowledge in this technical field.
  • it may have a chemical structure different from the above formula (I), but for those skilled in the art, it can sufficiently be recognized that it is in an isomeric relationship and falls within the scope of the present invention.
  • the benzamide derivative of the above formula (I) or its salt (hereinafter referred to simply as the compound of the present invention) can be produced by the following Process [1 ] and in accordance with a usual process for producing a salt.
  • Process [1 ] PROCESS [1 ]
  • R 1 and R 2 are as defined above, and Z is hydroxy, alkoxy or halogen.
  • halogen an atom of fluorine, chlorine, bromine or iodine may be mentioned.
  • the salt of the compound of the formula (II) includes all kinds so long as they are acceptable in this technical field, and it may, for example, be an inorganic acid salt such as a hydrochloride or a sulfate ; or an organic acid salt such as an acetate or a methanesulfonate.
  • the reaction of the Process [1] may be carried out usually in the presence of a base and a solvent.
  • a base one or more may suitably be selected from e.g. alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine; and pyridines such as pyridine and 4-dimethylaminopyridine.
  • alkali metals such as sodium and potassium
  • alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide
  • carbonates such as sodium carbonate and potassium carbonate
  • bicarbonates such as
  • the solvent is not particularly limited so long as the reaction thereby proceeds, and one or more may suitably be selected from e.g. aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, dichloroethane, trichloroethane and chlorobenzene; ethers such as dioxane, tetrahydrofuran, diethyl ether and
  • esters such as methyl acetate and ethyl acetate; polar aprotic solvents such as dimethylsulfoxide, sulfolane, dimethylacetamide, dimethylformamide and N-methylpyrrolidone; nitriles such as acetonitrile and propiononitrile; ketones such as acetone and methyl ethyl ketone; and water.
  • polar aprotic solvents such as dimethylsulfoxide, sulfolane, dimethylacetamide, dimethylformamide and N-methylpyrrolidone
  • nitriles such as acetonitrile and propiononitrile
  • ketones such as acetone and methyl ethyl ketone
  • water water.
  • the reaction of the Process [1 ] may be carried out in the presence of a dehydration-condensation agent as the case requires.
  • a dehydration-condensation agent one or more may suitably be selected from e.g. ⁇ , ⁇ '- dicyclohexylcarbodiimide, chlorosulfonyl isocyanate, ⁇ , ⁇ '-carbonyldiimidazole and trifluoroacetic anhydride.
  • the reaction temperature is usually from 0 to 100°C, preferably from 0 to 50°C, and the reaction time is usually from about 0.1 to 48 hours, preferably from about 0.5 to 24 hours.
  • the compound of the formula (II) as a starting material of the above Process [1 ] may be produced, for example, by the following Process [A].
  • R 1 and R 2 are as defined above.
  • the reduction reaction of the Process [A] is a reaction of the compound of the formula (IV) with a reducing agent.
  • the reduction reaction may, for example, be the catalytic hydrogenation reaction or a reduction reaction by a metal hydride described below, and by either of the reactions, it is possible to produce the compound of the formula (II).
  • one or more may suitably be selected from e.g. hydrogen, formic acid and ammonium formate.
  • the catalytic hydrogenation reaction may be carried out usually in the presence of a catalyst and a solvent.
  • a catalyst one or more may suitably be selected from e.g. platinum, platinum oxide, platinum black, Raney nickel, palladium, palladium- carbon, rhodium and rhodium-alumina.
  • the solvent is not particularly limited so long as the reaction thereby proceeds, and one or more may suitably be selected from e.g. aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; esters such as methyl acetate and ethyl acetate; acid amides such as dimethylacetamide, dimethylformamide and N-methylpyrrolidone; alcohols such as methanol, ethanol, propanol and butanol; and water.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclo
  • the reaction temperature of the catalytic hydrogenation reaction is usually from
  • reaction time is usually from about 0.5 to 96 hours, preferably from about 1 to 48 hours.
  • the reducing agent used for the reduction reaction by a metal hydride may, for example, be a metal hydride such as sodium borohydride or lithium aluminium hydride.
  • the reduction reaction by a metal hydride may be carried out in the presence of e.g. titanium tetrachloride or molybdenum oxide, as the case requires.
  • the reduction reaction by a metal hydride may be carried out usually in the presence of a solvent.
  • the solvent is not particularly limited so long as the reaction thereby proceeds, and one or more may suitably be selected from e.g. ethers such as dioxane, tetrahydrofuran, diethyl ether and dimethoxyethane; alcohols such as methanol, ethanol, propanol and butanol; and water.
  • the reaction temperature of the reduction reaction by a metal hydride is usually from -100 to 150°C, preferably from -10 to 100°C, and the reaction time is usually from about 0.5 to 96 hours, preferably from about 1 to 48 hours.
  • [A] may be produced, for example, in accordance with the following Process [B].
  • R 1 and R 2 are as defined above.
  • the salt of NH 2 OH includes all kinds so long as they are acceptable in this technical field, and for example, an inorganic acid salt such as a hydrochloride or a sulfate; or an organic acid salt such as a methanesulfonate may be mentioned.
  • the reaction of the Process [B] may be carried out in the presence of a base, as the case requires.
  • a base one or more may suitably be selected from e.g. alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine; pyridines such as pyridine and 4-dimethylaminopyridine; and acetates such as sodium acetate and potassium acetate.
  • alkali metals such as sodium and potassium
  • alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide
  • carbonates
  • the reaction of the Process [B] may be carried out in the presence of a catalytic amount of e.g. hydrochloric acid, sulfuric acid or p-toluenesulfonic acid, as the case requires.
  • a catalytic amount of e.g. hydrochloric acid, sulfuric acid or p-toluenesulfonic acid as the case requires.
  • the reaction of the Process [B] may be carried out usually in the presence of a solvent.
  • the solvent is not particularly limited so long as the reaction thereby proceeds, and one or more may suitably be selected from e.g. aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as hexane, heptane, petroleum ether, ligroin and cyclohexane; ethers such as dioxane,
  • esters such as methyl acetate and ethyl acetate
  • polar aprotic solvents such as dimethylsulfoxide, sulfolane
  • amines or pyridines may also be used with the solvent.
  • the reaction temperature of the Process [B] is usually from 20 to 150°C, preferably from 50 to 100°C, and the reaction time is usually from about 0.5 to 96 hours, preferably from about 1 to 48 hours.
  • the insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention is useful, for example, as an agent to control insects, mites, nematodes or soil pests which become problematic in the agricultural and horticultural fields, or as an agent to control insects or mites parasitic on animals.
  • the insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention is useful in the agricultural and horticultural field. Specifically, it is effective to control insects, e.g.
  • aphids such as green peach aphid (Mvzus persicae) and cotton aphid (Aphis qossvpii); agricultural insect pests such as diamondback moth (Plutella xyjostella), cabbage armyworm (Mamestra brassjcae), common cutworm
  • mites e.g. plant parasitic mites such as two-spotted spider mite (Tetranvchus urticae), carmine spider mite (Tetranvchus cinnabarinus).
  • mites e.g. plant parasitic mites such as two-spotted spider mite (Tetranvchus urticae), carmine spider mite (Tetranvchus cinnabarinus).
  • Chelacaropsis moorei; nematodes e.g. plant parasitic nematodes such as root-knot nematodes, cyst nematodes, root-lesion nematodes, white-tip nematode
  • the compound of the present invention has excellent systemic properties, and by the application of the insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention to soil treatment, not only noxious insects, noxious mites, noxious nematodes, noxious gastropods and noxious isopods in soil but also foliage pests can be controlled.
  • Another preferred embodiments of the agricultural and horticultural insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention may be insecticides, miticides, nematicides or soil pesticides which collectively control the above-mentioned plant parasitic mites, agricultural insect pests, plant parasitic nematodes, gastropods and soil pests.
  • the insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention is usually formulated by mixing the compound with various agricultural adjuvants and used in the form of a formulation such as a dust, granules, water-dispersible granules, a wettable powder, a water-based suspension concentrate, an oil-based suspension concentrate, a water soluble powder, an emulsifiable
  • Such agricultural adjuvants include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch; solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethylsulfoxide, ⁇ , ⁇ -dimethylformamide, N,N- dimethylacetamide, N-methyl-2-pyrrolidone, and alcohol; anionic surfactants such as a salt of fatty acid,
  • polycarboxylate a salt of alkylsulfuric acid ester, an alkyi sulfate, an alkylaryl sulfate, an alkyi diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyi sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether
  • a polystyrene sulfonate a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyi ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, and a salt of a condensate of naphthalene sulfonate with formaldehyde; nonionic surfactants such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer,
  • each of the components as such adjuvants may be one or more suitably selected for use, so long as the purpose of the present invention can thereby be accomplished. Further, other than the above-mentioned adjuvants, some among those known in this field may suitably be selected for use. For example, various adjuvants which are commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a phytotoxicity reducing agent, an anti-mold agent, and so on, may also be employed.
  • the weight ratio of the compound of the present invention to the various agricultural adjuvants is usually from 0.001 :99.999 to 95:5, preferably from
  • such a formulation may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders e.g. surfactants, vegetable oils or mineral oils may be added thereto, as the case requires.
  • a diluent such as water
  • various spreaders e.g. surfactants, vegetable oils or mineral oils
  • the application of the insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention cannot generally be defined, as it varies depending upon the weather conditions, the type of the formulation, the application season, the application site or the types or degree of outbreak of the pest insects.
  • the present invention includes such a method for controlling insects, mites, nematodes or soil pests, particularly for controlling plant parasitic mites, agricultural insect pests or plant parasitic nematodes by such applications.
  • compositions of the insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention or their diluted compositions may be applied by conventional methods for application which are commonly employed, such as spraying (e.g. jetting, misting, atomizing, powder or grain scattering or dispersing in water), soil application (e.g. mixing or drenching), surface application (e.g. coating, powdering or covering) or impregnation to obtain poisonous feed. Further, it is possible to feed domestic animals with a food containing the above active ingredient and to control the outbreak or growth of pests, particularly insect pests, with their excrements. Furthermore, the active ingredient may also be applied by a so-called ultra low-volume application method. In this method, the composition may be composed of 100% of the active ingredient.
  • insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention may be mixed with or may be used in combination with other agricultural chemicals, fertilizers or phytotoxicity-reducing agents, whereby synergistic effects or activities may sometimes be obtained.
  • other agricultural chemicals include, for example, a herbicide, an insecticide, a miticide, a nematicide, a soil pesticide, a fungicide, an antivirus agent, an attractant, an antibiotic, a plant hormone, a plant growth regulating agent, and so on.
  • an insecticidal, miticidal, nematicidal or soil pesticidal composition having a compound of the present invention mixed with or used in combination with one or more active compounds of other agricultural chemicals the application range, the application time, the pesticidal activities, etc. may be improved to preferred directions.
  • the compound of the present invention and the active compounds of other agricultural chemicals may separately be formulated so that they may be mixed for use at the time of application, or they may be formulated together.
  • the present invention includes such an insecticidal, miticidal, nematicidal or soil pesticidal composition.
  • the mixing ratio of the compound of the present invention to the active compounds of other agricultural chemicals can not generally be defined, since it varies depending upon the weather conditions, the types of formulations, the application time, the application site, the types or degree of outbreak of insect pests, etc., but it is usually within a range of from 1 :300 to 300:1 , preferably from 1 :100 to 100:1 , by weight. Further, the dose for the application is such that the total amount of the active
  • the present invention includes a method for controlling insects, mites, nematodes or soil pests by an application of such an insecticidal, miticidal, nematicidal or soil pesticidal composition.
  • the active ingredient compounds of an insect pest control agents such as the insecticide, the miticide, the nematicide or the soil insect pesticide in the above- mentioned other agricultural chemicals, include, for example, (by common names, some of them are still in an application stage, or test codes of Japan Plant Protection Association):
  • organic phosphate compounds such as profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulprofos, thiometon, vamidothion, pyraclofos,
  • pyridaphenthion pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos, phosphamidon, phosmet and phorate;
  • carbamate compounds such as carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC and fenothiocarb;
  • nereistoxin derivatives such as cartap, thiocyclam, bensultap and thiosultap- sodium;
  • organic chlorine compounds such as dicofol, tetradifon, endosulfan, dienochlor and dieldrin
  • organic metal compounds such as fenbutatin oxide and cyhexatin
  • pyrethroid compounds such as fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, ethofenprox, flufenprox, cyfluthrin, fenpropathrin, flucythrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethrin, allethrin,
  • benzoylurea compounds such as diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron, hexaflumuron, bistrifluron,
  • juvenile hormone-like compounds such as methoprene, pyriproxyfen, fenoxycarb and diofenolan;
  • pyridazinone compounds such as pridaben
  • pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, ethiprole, tolfenpyrad, acetoprole, pyrafluprole and pyriprole;
  • neonicotinoids such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, nidinotefuran, dinotefuran and nithiazine;
  • hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide and halofenozide;
  • pyridine compounds such as pyridalyl and flonicamid
  • cyclic keto-enol compounds such as spirodiclofen, spiromesifen and
  • strobilurin compounds such as fluacrypyrim
  • pyrimidinamine compounds such as flufenerim
  • microbial agricultural chemicals such as insecticidal crystal proteins produced by Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or Bacillus thuringiensis, insect viruses, etomopathogenic fungi, and nematophagous fungi; antibiotics or semisynthetic antibiotics, such as avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE- 175, abamectin, emamectin and spinetoram; natural products, such as azadirachtin and rotenone; and repellents, such as deet.
  • microbial agricultural chemicals such as insecticidal crystal proteins produced by
  • the active ingredient compounds of the fungicide in the above-mentioned other agricultural chemicals include, for example, (by common names, some of them are still in an application stage, or test codes of Japan Plant Protection Association):
  • anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, and cyprodinil
  • triazoropyrimidine compounds such as 5-chloro-7-(4-methylpiperidin-1-yl)-6-
  • pyridinamine compounds such as fluazinam
  • azole compounds such as triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, myclobutanil, cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole,
  • tetraconazole oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole, fluquinconazole, fenbuconazole, bromuconazole,
  • quinoxaline compounds such as quinomethionate
  • dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb and thiram;
  • organic chlorine compounds such as fthalide, chlorothalonil and quintozene
  • imidazole compounds such as benomyl, cyazofamid, thiophanate-methyl, carbendazim, thiabendazole and fuberiazole;
  • cyanoacetamide compounds such as cymoxanil
  • anilide compounds such as metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, ofurace, benalaxyl, benalaxyl-M (another name: kiralaxyl, chiralaxyl), furalaxyl, cyprofuram, carboxin, oxycarboxin, thifluzamide, boscalid, bixafen, isotianil, tiadinil and sedaxane;
  • sulfamide compounds such as dichlofluanid
  • copper compounds such as cupric hydroxide and oxine copper
  • isoxazole compounds such as hymexazol
  • organophosphorus compounds such as fosetyl-AI, tolclofos-methyl, S-benzyl 0,0-diisopropylphosphorothioate, O-ethyl S,S-diphenylphosphorodithioate, aluminum ethylhydrogen phosphonate, edifenphos, and iprobenfos;
  • phthalimide compounds such as captan, captafol and folpet;
  • dicarboximide compounds such as procymidone, iprodione and vinclozolin; benzanilide compounds, such as flutolanil and mepronil;
  • amide compounds such as penthiopyrad, mixture of 3-(difluoromethyl)-1-methyl- N-[(1 RS,4SR,9RS)-1 ,2,3,4-tetrahydro-9-isopropyl-1 ,4-methanonaphthalen-5- yl]pyrazole-4-carboxamide and 3-(difluoromethyl)-1-methyl-N-[(1 RS,4SR,9SR)-1 ,2,3,4- tetrahydro-9-isopropyl-1 ,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide
  • benzamide compounds such as fluopyram and zoxamide
  • piperazine compounds such as triforine
  • pyridine compounds such as pyrifenox
  • carbinol compounds such as fenarimol
  • piperidine compounds such as fenpropidin
  • morpholine compounds such as fenpropimorph and tridemorph
  • organotin compounds such as fentin hydroxide and fentin acetate
  • urea compounds such as pencycuron
  • cinnamic acid compounds such as dimethomorph and flumorph
  • phenylcarbamate compounds such as diethofencarb
  • cyanopyrrole compounds such as fludioxonil and fenpiclonil
  • strobilurin compounds such as azoxystrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin, pyraclostrobin, and fluoxastrobin; oxazolidinone compounds, such as famoxadone;
  • thiazolecarboxamide compounds such as ethaboxam
  • valinamide compounds such as iprovalicarb and benthiavalicarb-isopropyl
  • acylamino acid compounds such as methyl N-(isopropoxycarbonyl)-L-valyl- (3RS)-3-(4-chlorophenyl)- -alaninate (valiphenalate);
  • imidazolinone compounds such as fenamidone
  • hydroxyanilide compounds such as fenhexamid
  • benzenesulfonamide compounds such as flusulfamide
  • oxime ether compounds such as cyflufenamid
  • antibiotics such as validamycin, kasugamycin and polyoxins
  • guanidine compounds such as iminoctadine and dodine
  • quinoline compounds such as 6-tert-butyl-8-fluoro-2,3-dimethylquinolin- 4-yl acetate (tebufloquin);
  • thiazolidine compounds such as (Z)-2-(2-fluoro-5-(trifluromethyl)phenylthio)-2-(3- (2-methoxyphenyl)thiazolidin-2-yliden)acetonitrile (flutianil);
  • agricultural chemicals which may be used in admixture with or in combination with the compounds of the present invention, may, for example, be the active ingredient compounds in the herbicides as disclosed in The Pesticide Manual (15th edition), particularly those of soil treatment type.
  • the insecticide, miticide, nematicide or soil pesticide containing the compound of the present invention is useful as an agent to control insects or mites parasitic on animals. Specifically, it is effective for controlling e.g. harmful external parasites which are parasitic on the body surface of host animals (such as the back, the axilla, the lower abdomen or inside of the thigh) or harmful internal parasites which are parasitic in the body of host animals (such as the stomach, the intestinal tract, the lung, the heart, the liver, the blood vessels, the subcutis or lymphatic tissues), but they are particularly effective for controlling the external parasites.
  • harmful external parasites which are parasitic on the body surface of host animals (such as the back, the axilla, the lower abdomen or inside of the thigh)
  • harmful internal parasites which are parasitic in the body of host animals (such as the stomach, the intestinal tract, the lung, the heart, the liver, the blood vessels, the subcutis or lymphatic tissues), but they are particularly effective for controlling the external parasite
  • the external parasites may, for example, be animal parasitic acarus or fleas. Their species are so many that it is difficult to list all of them, and therefore, their typical examples will be given.
  • the animal parasitic acarus may, for example, be ticks such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphvsalis lonqicornis, Haemaphvsalis flava, Haemaphvsalis campanulata, Haemaphvsalis concinna, Haemaphvsalis iaponica, Haemaphvsalis kitaokai, Haemaphvsalis ias, Ixodes ovatus, Ixodes
  • sarcoptic mange mites such as Psoroptes cuniculi, Chorioptes bovis, Otodectes cvnotis, Sarcoptes scabiei. and Notoedres cati
  • Demodicidae such as Demodex canis.
  • it is particularly effective for the control of ticks.
  • the animal parasitic fleas may, for example, be externally parasitic wingless insects belonging to Siphonaptera, more specifically, fleas belonging to Pulicidae,
  • Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Echidnophaqa qallinacea, Xenopsylla cheopis, Leptopsylla seqnis, Nosopsyllus fasciatus, and Monopsyllus anisus.
  • the agent to control insects or mites parasitic on animals, containing the compounds of the present invention, is particularly effective for the control of fleas belonging to Pulicidae, particularly Ctenocephalides canis and Ctenocephalides felis, among them.
  • Other external parasites may, for example, be sucking lice (Anoplura) such as shortnosed cattle louse (Haematopinus eurvsternus), horse sucking louse (Haematopinus asini), sheep louse, longnosed cattle louse (Linognathus vituli), and head louse (Pediculus capitis); biting lice such as dog biting louse (Trichodectes canis); and blood-sucking dipterous insects such as horsefly (Tabanus trigonus), biting midges (Culicoides schultzei), and blackfly (Simulium ornatum).
  • the internal parasites may, for example, be nematodes such as lung worms, whipworms (Trichuris), tuberous worms, gastric parasites, ascaris, and filarioidea; cestoda such as Spirometra erinacei, Diphyllobothrium latum, Dipylidium caninum, Taenia multiceps, Echinococcus granulosus, and Echinococcus multilocularis; trematoda such as Schistosoma iaponicum and Fasciola hepatica; and protozoa such as coccidia, malaria parasites (Plasmodium malariae), intestinal sarcocyst, toxoplasma, and Cryptosporidium.
  • nematodes such as lung worms, whipworms (Trichuris), tuberous worms, gastric parasites, ascaris, and filarioidea
  • cestoda such as Spirometra erinacei, Di
  • the host animals may, for example, be pet animals, domestic animals, and poultry, such as dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (such as pigeons, parrots, hill mynas, Java sparrows, honey parrots, lovebirds and canaries), cows, horses, pigs, sheep, ducks and chickens.
  • the agent to control insects or mites parasitic on animals, containing the compounds of the present invention is particularly effective for the control of pests parasitic on pet animals or domestic animals, especially for the control of external parasites, among them.
  • the compound of the present invention when used as an agent to control insects or mites parasitic on animals, it may be used as it is or may be used together with suitable adjuvants, as formulated into various formulations such as a dust, granules, tablets, a powder, capsules, a soluble concentrate, an emulsifiable
  • compositions may be formulated into any type of formulation which is commonly used in this field, so long as it is suitable for the purpose of the present invention.
  • the adjuvants to be used for formulations may, for example, be anionic surfactants or nonionic surfactants exemplified above as
  • a cationic surfactant such as cetyl trimethylammonium bromide
  • a solvent such as water, acetone, acetonitrile, N-methylacetamide, N,N- dimethylacetamide, ⁇ , ⁇ -dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol n-butyl ether, dipropylene glycol monomethyl ether, or dipropylene glycol n-butyl ether; an antioxidant such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid
  • one or more of the respective components of these adjuvants may be suitably selected for use, so long as such will not depart from the purpose of the present invention. Further, other than the above-mentioned adjuvants, some among those known in this field may suitably be selected for use, and still further, some among the above-mentioned various adjuvants to be used in the agricultural and horticultural field may suitably be selected for use.
  • the blend ratio of the compound of the present invention to various adjuvants is usually from 0.1 :99.9 to 90:10, by weight. In the actual use of such a formulation, it may be used as it is, or may be diluted to a predetermined concentration with a diluent such as water, and various spreaders (e.g. surfactants, vegetable oils or mineral oils) may be added thereto, as the case requires.
  • a diluent such as water
  • various spreaders e.g. surfactants, vegetable oils or mineral oils
  • Administration of the compound of the present invention to a host animal is carried out orally or parenterally.
  • an oral administration method a method of administering a tablet, a liquid agent, a capsule, a wafer, a biscuit, a minced meat or other feed, containing the compound of the present invention, may be mentioned.
  • a parenteral administration method there may, for example, be mentioned a method wherein the compound of the present invention is formulated into a suitable formulation and then taken into the body by e.g.
  • intravenous administration intramuscular administration, intradermal administration, hypodermic administration, etc.
  • a method of embedding a resin fragment or the like containing the compound of the present invention under the skin of the host animal
  • the dose of the compound of the present invention to a host animal varies depending upon the administration method, the purpose of administration, the
  • deceased symptom, etc. but it is usually administered in a proportion of from 0.01 mg to 100 g, preferably from 0.1 mg to 10 g, per 1 kg of the body weight of the host animal.
  • the present invention also includes a method for controlling an insects or mites parasitic on animals by the above-mentioned administration method or by the above- mentioned dose, particularly a method for controlling external parasites or internal parasites.
  • the present invention by controlling pests parasitic on animals as described above, it is possible to prevent or cure various diseases of the host animal thereby caused in some cases.
  • the present invention also includes a
  • preventive or therapeutic agent for an animal disease caused by parasites containing the compound of the present invention as an active ingredient, and a method for preventing or curing an animal disease caused by parasites.
  • the compound of the present invention When the compound of the present invention is used as an agent to control insects or mites parasitic on animals, various vitamins, minerals, amino acids, nutrients, enzymes, antipyretics, sedatives, antiphlogistics, fungicides, colorants, aromatic substances, preservatives, etc., may be used in admixture with or in combination with the adjuvants. Further, as the case requires, other animal drugs or agricultural chemicals, such as vermicides, anti-coccidium agents, insecticides, miticides, pulicides, nematicides, bactericides or antibacterial agents, may be mixed or combined for use, whereby improved effects may sometimes be obtained.
  • the present invention includes such a mixed pesticidal composition having the above-mentioned various components mixed or combined for use, and further a method for controlling a pest by using it, particularly a method for controlling external parasites or internal parasites.
  • R 1 a is Ci -3 alkyl
  • R 2 a is C 2- 8 alkyl or C 3-8 cycloalkyl
  • R 1 a and R a are different from each other
  • the methine carbon to which R 1 a and R 2 a are bonded is the chiral center.
  • Typical examples of the compound of the above formula (I) will be given in Table 1. These compounds can be prepared based on the above-described Preparation Examples 1 and 2 or the above-described various production processes.
  • Table 1 No. represents the Compound No., Me methyl, Et ethyl, n-Pr normal-propyl, i-Pr isopropyl, c-Pr cyclopropyl, c-Bu cyclobutyl, t-Bu tertiary-butyl, n-Pentyl normal-pentyl and c-Hexyl cyclohexyl, and the temperature shown as the physical properties is the melting point.
  • R/S represents the type of the enantiomer.
  • TEST EXAMPLE 1 Test on southern root-knot nematode (Meloidqyne incognita) To 400 ml of the soil contaminated by southern root-knot nematode, 7 ml of a chemical solution having the concentration of the compound of the present invention adjusted to be 400 ppm, was poured, followed by mixing so that the compound was uniformly dispersed. The treated soil was put into a pot (diameter: 9 cm, height: 8 cm), and then a tomato seedling in 2-leaf stage was transplanted and placed in a greenhouse. After three to four weeks from the transplantation of the tomato, the root knot index was determined based on the standards shown in Table 2. The compound Nos. 1 , 2, 4, 7 and 19 were at a level of a root knot index of not more than 1. TABLE 2
  • a gelatin capsule containing the compound of the present invention at a dose of 10 mg/kg weight is applied to a dog (Beagle, 8 months old), and immediately after the application, about 50 young mites of Haemaphvsalis longicornis are released on the auricle of the dog and artificially parasitized. After the treatment, observation is carried out to inspect the parasitic number, the fallen number and the mortality of the fallen Haemaphvsalis lonqicornis. As a result, the compound of the present invention is effective to have the parasitized Haemaphvsalis longicornis fallen or dead.
  • Pesticidal test against cat flea employing a dog
  • a gelatin capsule containing the compound of the present invention at a dose of 10 mg/kg weight is applied to a dog (Beagle, 8 months old), and immediately after the application, about 100 non-bloodsucked adults of cat flea are released on the dorsal fur of the dog and artificially parasitized. After the treatment, the cat flea is recovered by means of a flea catching comb, and the parasitized number is counted. As a result, the compound of the present invention is effective to control the parasitizing of cat flea.
  • the above components are uniformly mixed to obtain a wettable powder.
  • the above components are uniformly mixed to obtain a dust.
  • the mixture of the above components is mixed with compound of the present invention in a weight ratio of 4:1 to obtain a wettable powder.
  • the above components are uniformly mixed and pulverized to obtain a base liquid, and
  • the above components (1) to (3) are preliminarily uniformly mixed and diluted with a proper amount of acetone, and then the mixture is sprayed onto the component (4), and acetone is removed to obtain granules.
  • the above components are uniformly mixed and dissolved to obtain an ultra low volume formulation.
  • the above components are uniformly mixed and pulverized to obtain a water- based suspension concentrate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Depuis de nombreuses années, de nombreux insecticides, miticides, nématicides ou pesticides du sol ont été utilisés, mais un grand nombre d'entre eux ont différents problèmes de sorte que les effets soient insuffisants, leur utilisation est restreinte étant donné que des insectes, etc., ont acquis une résistance, etc. En conséquence, il est souhaité de développer un nouvel insecticide, miticide, nématicide ou pesticide du sol sensiblement exempt de tels problèmes. Par conséquent, la présente invention concerne un nouvel insecticide, miticide, nématicide ou pesticide du sol ayant un effet de lutte très élevé contre les insectes, les mites, les nématodes ou les organismes nuisibles du sol à une dose faible. La présente invention concerne un insecticide, miticide, nématicide ou pesticide du sol contenant un dérivé de benzamide représenté par la formule (I) ou son sel, en tant que substance active : dans lequel R1 est un atome d'hydrogène ou un alkyle en C1-3, et R2 est un alkyle en C2-8 ou un cycloalkyle en C3-8.
PCT/JP2011/070090 2010-09-01 2011-08-30 Dérivé de benzamide ou son sel, et insecticide, miticide, nématicide ou pesticide du sol contenant celui-ci Ceased WO2012029968A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0243668A2 (fr) * 1986-04-04 1987-11-04 Bayer Ag Benzamides N-substitués
EP0323637A1 (fr) * 1988-01-07 1989-07-12 Bayer Ag L(-) N-(1,1,1-trifluoro-2-propyl)-2,6-difluorobenzamide
WO2001091558A1 (fr) 2000-05-31 2001-12-06 Bayer Aktiengesellschaft Agents herbicides a base d'amides d'acide carboxylique substitues
JP2010195397A (ja) 2002-11-26 2010-09-09 Valeo Wischersysteme Gmbh ワイパブレードの組立品およびワイパの組立品
JP2010202545A (ja) * 2009-03-02 2010-09-16 Ishihara Sangyo Kaisha Ltd Ｎ−（１−シクロプロピルエチル）−２，６−ジフルオロベンズアミド又はその塩及びそれらを含有する有害生物防除剤

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0243668A2 (fr) * 1986-04-04 1987-11-04 Bayer Ag Benzamides N-substitués
US4840969A (en) 1986-04-04 1989-06-20 Bayer Aktiengesellschaft N-substituted benzamides
EP0323637A1 (fr) * 1988-01-07 1989-07-12 Bayer Ag L(-) N-(1,1,1-trifluoro-2-propyl)-2,6-difluorobenzamide
EP0323637B1 (fr) 1988-01-07 1992-12-16 Bayer Ag L(-) N-(1,1,1-trifluoro-2-propyl)-2,6-difluorobenzamide
WO2001091558A1 (fr) 2000-05-31 2001-12-06 Bayer Aktiengesellschaft Agents herbicides a base d'amides d'acide carboxylique substitues
JP2010195397A (ja) 2002-11-26 2010-09-09 Valeo Wischersysteme Gmbh ワイパブレードの組立品およびワイパの組立品
JP2010202545A (ja) * 2009-03-02 2010-09-16 Ishihara Sangyo Kaisha Ltd Ｎ−（１−シクロプロピルエチル）−２，６−ジフルオロベンズアミド又はその塩及びそれらを含有する有害生物防除剤

Non-Patent Citations (2)

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Title
DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 18 March 2002 (2002-03-18), XP002662564, retrieved from STN Database accession no. 401587-35-7 *
DATABASE REGISTRY [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 30 August 2006 (2006-08-30), XP002662565, retrieved from STN Database accession no. 905416-49-1 *

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