WO2000003596A1 - Utilisation de o-alkyle-carbamates substitues pour lutter contre des parasites animaux - Google Patents

Utilisation de o-alkyle-carbamates substitues pour lutter contre des parasites animaux Download PDF

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Publication number
WO2000003596A1
WO2000003596A1 PCT/EP1999/004745 EP9904745W WO0003596A1 WO 2000003596 A1 WO2000003596 A1 WO 2000003596A1 EP 9904745 W EP9904745 W EP 9904745W WO 0003596 A1 WO0003596 A1 WO 0003596A1
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WO
WIPO (PCT)
Prior art keywords
diyl
alkyl
optionally
cyano
methyl
Prior art date
Application number
PCT/EP1999/004745
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German (de)
English (en)
Inventor
Hans-Jochem Riebel
Johannes Rudolf Jansen
Joachim Kluth
Stefan Lehr
Ulrike Wachendorff-Neumann
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU50329/99A priority Critical patent/AU5032999A/en
Publication of WO2000003596A1 publication Critical patent/WO2000003596A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring

Definitions

  • the invention relates to the use of partially known substituted O-alkyl carbamates for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector.
  • R 1 for optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, aryl.
  • R ⁇ represents hydrogen or alkyl, or together with R.1 stands for optionally branched and optionally interrupted by oxygen alkanediyl, and R 3 represents optionally substituted aryl or heteroaryl,
  • insects are very suitable for controlling animal pests, in particular insects, arachnids and nematodes.
  • the compounds of the formula (I) optionally contain one or more centers of chirality and can then be present in various enantiomeric (R- and S-configured) or diastereomeric forms.
  • the invention relates both to the use of the individual possible enantiomeric or diastereomeric forms of
  • Formula (I) provides a general definition of the substituted O-alkylcarbamates which can be used according to the invention.
  • A preferably represents straight-chain or branched Ci-Cg-alkanediyl which is optionally substituted by cyano, halogen or Ci - Czi-alkoxy.
  • Cj-Cg-oxaalkanediyl or Ci-Cg-thiaalkanediyl the oxaalkanediyl and thiaalkanediyl groups in each case being connected to the carbamate oxygen atom via a carbon atom, or for C3-Cg-cycloalkanediyl or C3- which are optionally substituted by halogen C5-CVCI0-alkanediyloxy.
  • R 1 preferably represents optionally by cyano.
  • Benzimidazolyl indazolyl, oxadiazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyridinyl -CC-C4-alkyl, pyrimidinyl, pyrimidinyl -CC-C4-alkyl, pyrazinyl, pyridazinyl, quinolyl. Isoquinolyl, quinoxalinyl. Cinnolinyl or phthalazinyl.
  • R 2 preferably represents hydrogen or C 1 -C 6 -alkyl, or together with R * represents optionally branched and optionally interrupted by C 2 -C 6 -alkanediyl.
  • R 3 preferably represents in each case optionally by nitro, cyano.
  • Cinnolinyl, phthalazinyl Cinnolinyl, phthalazinyl.
  • R 1 particularly preferably represents in each case optionally by cyano, fluorine,
  • Chlorine Methoxy. Ethoxy, n- or i-propoxy substituted methyl. Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally by cyano. Fluorine. Chlorine. Methyl or ethyl substituted cyclopropyl, cyclobutyl,
  • Cyclopentyl Cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclo- pentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n - or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, di-fluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulf
  • R 2 particularly preferably represents hydrogen, methyl. Ethyl, n- or i-propyl. or together with R 1 for butane-1,4-diyl. Pentane-l, 5-diyl or 3-oxapentane-l, 5-diyl.
  • R 3 particularly preferably represents optionally by nitro, cyano.
  • a very particularly preferred group of substituted O-alkyl carbamates which can be used according to the invention are those ⁇ / compounds of the formula (I) in which
  • A represents 4-oxa-butane-2,4-diyl (-CH (CH 3 ) CH 2 O-) or 5-oxapentane-3,5-diyl (-CH (C 2 H 5 ) CH 2 O-) ,
  • R 1 for by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl.
  • Trifluorme hyl methoxy, ethoxy, n- or i-propoxy, Difluorme hoxy. Trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio. Difluoromethylthio. Trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl. Methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl.
  • n- or i-butyroyl methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.
  • Dimethylaminocarbonyl Dimethylaminosulfonyl, cyclopropylcarbonyl, methylenedioxy, difluoromethylenedioxy.
  • Ethylene dioxy trifluoroethylene dioxy or tetrafluoroethylene dioxy, single or double, identical or different substituted phenyl.
  • R 2 represents hydrogen
  • R 3 for by nitro, cyano, fluorine, chlorine. Bromine, methyl, ethyl. n- or i-propyl. n-. i-, s- or t-butyl. Trifluoromethyl, methoxy, ethoxy. n- or i-propoxy.
  • Difluoromethoxy trifluoromethoxy.
  • Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitutions the substituents can be the same or different.
  • hydrocarbon chains are like alkyl.
  • Alkanediyl Alkenyl or alkynyl - also in combination with heteroatoms, such as in alkoxy or alkylthio - in each case straight-chain or branched.
  • Halogen generally represents fluorine, chlorine. Bromine or iodine, preferably for fluorine. Chlorine or bromine, especially for fluorine or chlorine.
  • substituted O-alkylcarbamates of the general formula (I) to be used according to the invention are known and / or can be prepared by processes known per se (see US-A-5099059, US-A-5152827, US-A-5194661, US-A-5399545 / WO-A-9410132, DE-A-19746267).
  • R 1 and R 2 have the meaning given above
  • an acid acceptor e.g. Triethylamine or potassium carbonate.
  • a diluent such as e.g. Methylene chloride or 1,2-dichloroethane. implemented at temperatures between -30 ° C and + 100 ° C (see the manufacturing examples),
  • R 2 in the formula (I) is hydrogen - if one
  • R 1 has the meaning given above
  • reaction auxiliary e.g. Dibutyltin dilaurate
  • a diluent such as e.g. 1,4-Dioxane
  • the active compounds of the general formula (I) are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are used in agriculture, in forests, in stock and
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Symphyla for example, Scutigerella immaculata.
  • Thysanura for example Lepisma saccharina.
  • Collembola for example Onychiurus armatus.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp ..
  • Rhipicephalus spp. Amblyomma spp. Hyalomma spp., Ixodes spp., Psoroptes spp.,
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp .. Tetranychus spp ..
  • the plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus spp., Ditylenchus spp., Tylenchulus spp., Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., ., Tylenchus spp., Helicotylenchus spp., Rotylenchus spp., Tylenchulus spp ...
  • the compounds of the general formula (I) which can be used according to the invention are notable in particular for their strong insecticidal activity.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes.
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as
  • Chlorobenzenes Chlorethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters. Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylene formamide and dimethyl sulfoxide, and water.
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
  • alcohols such as butanol or glycol
  • Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylene formamide and dimethyl sulfoxide, and water.
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules Question: eg broken and fractionated natural rocks such as calcite.
  • Ether e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide. Ferrocyan blue and organic dyes such as alizarin. Azo and metal phthalocyanine dyes and trace nutrients such as salts of iron. Manganese. Bor.Copper. Cobalt. Molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active ingredients can be found in commercially available formulations and in the use forms prepared from these formulations in a mixture with other active ingredients, such as insecticides. Attractants, sterilants, bactericides, acaricides. Nematicides. Fungicides, growth regulators or herbicides are present. Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • Aldimorph Ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin. Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl.
  • Bialaphos Binapacryl, Biphenyl, Bitertanol. Blasticidin-S. Bromuconazole, bupirimate.
  • Buthiobate Calcium polysulfide, capsimycin, captafol, captan. Carbendazim. Carboxin,
  • Chloropicrin Chlorothalonil, chlozolinate, clozylacon, cufraneb. Cymoxanil, Cyproconazol, Cyprodinil, Cyprofuram, Debacarb, dichlorophen. Diclobutrazole.
  • Diclofluanide Diclomezin, Dicloran, Diethofencarb, Difenoconazol, Dimethirimol.
  • Dimethomo h diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione.
  • Etacazazole Ethirimol. Etridiazole, Famoxadone.
  • Fenapanil fenarimol, fenbuconazole.
  • Fenfuram Fenitropan.
  • Fenpiclonil fenpropidin, fenpropimorph, fentin acetate.
  • Fentin hydroxide Ferbam, Ferimzon. Fluazinam, flumetover, fluoromide,
  • Fluquinconazole Fluquinconazole, flurprimidol, flusilazole. Flusulfamide, flutolanil, flutriafol. Folpet.
  • Fosetvl-Alminium Fosetyl sodium. Fthalid. Fuberidazole. Furalaxyl, furametpyr.
  • Furcarbonil Furconazole, furconazole-cis. Furmecyclox. Guazatin, hexachlorobenzene. Hexaconazole. Hymexazole. Imazalil. Imibenconazole. Iminoctadine.
  • Iminoctadineal besilate Iminoctadine triacetate. Iodocarb, ipconazole. Iprobefos (IBP).
  • Copper preparations such as: copper hydroxide. Copper naphthenate, copper oxychloride.
  • Copper sulfate Copper oxide. Oxin-copper and Bordeaux mixture, Mancopper, Mancozeb. Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazole.
  • Validamycin A Vinclozolin. Viniconazole, zarilamide, zineb, ziram and Dagger G. OK-8705, OK-8801, ⁇ - (l, l-dimethylethyl) -ß- (2-phenoxyethyl) -lH-l, 2,4-triazole-l-ethanol , ⁇ - (2,4-Dichlo ⁇ henyl) -ß-fluoro-b-propyl-1 H-1, 2,4-triazole-1-ethanol, - (2,4-dichlo ⁇ henyl) -ß-methoxy-a-methyl - 1 H- 1, 2, 4-triazol-1-ethanol, - (5-methyl-1,3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] - 1 H-1, 2,4-triazole-1-ethanol,
  • N-Formyl-N-hydroxy-DL-alanine sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethyl phosphoramidothioate.
  • Buprofezin Butocarboxime, butylpyridaben. Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlo ⁇ yrifos. Chlo ⁇ yrifos M, cis-resmethrin, clocythrin, clofentezin, cyanophos, cycloprothrin.
  • Fenpropathrin Fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam. Flucycloxuron. Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion. Fosthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron. Hexythiazox, Imidacloprid, Iprobefos. Isazophos, Isofenphos, Isoprocarb. Isoxathione. Ivermectin, lambda cyhalothrin.
  • Mecarbam Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos. Methidathione.
  • Methiocarb Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram, Omethoat. Oxamyl, Oxydemethon M. Oxydepro fos. Parathion A, Parathion M, Permethrin. Phenthoat, Phorat, Phosalon. Phosmet, phosphamidon. Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos,
  • Promecarb Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos. Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, RH 5992, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebuffenozid, Tebufenpyrad, Tebupirimiphos, Teflubenzurin, Teflifarbutox, Teflifarbuthron, Teflutobhron, Teflutarbhrox , Thiofanox, Thiometone, Thionazine, Thuringiensin, Tralomethrin, Triarathen, Triazophos, Triazuron,
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.
  • Emulsifier 1900 parts by weight of methanol
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • a specified amount of active compound preparation of the desired concentration is pipetted onto a standardized amount of synthetic feed. After the methanol has evaporated, approx. 200-300 cabbage cockroach eggs (Plutella xylostella) are added to the feed.
  • the death of the eggs or larvae is determined in%. 100% means. that all animals were killed: 0% means that no animals were killed.

Abstract

L'invention concerne l'utilisation de O-alkyle-carbamates de la formule générale (I) dans laquelle A, R?1, R2 et R3¿ ont les significations mentionnées dans la description, pour lutter contre des parasites animaux, notamment des insectes, des arachnides et des nématodes, qui se présentent dans le domaine agricole, dans le domaine forestier, dans celui de la protection des matériaux et des produits stockés, ainsi que dans le secteur de l'hygiène.
PCT/EP1999/004745 1998-07-18 1999-07-07 Utilisation de o-alkyle-carbamates substitues pour lutter contre des parasites animaux WO2000003596A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU50329/99A AU5032999A (en) 1998-07-18 1999-07-07 Utilization of substituted o-alkyl-carbamates for combating animal pests

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19832444.8 1998-07-18
DE1998132444 DE19832444A1 (de) 1998-07-18 1998-07-18 Verwendung von substituierten O-Alkyl-carbamaten zur Bekämpfung tierischer Schädlinge

Publications (1)

Publication Number Publication Date
WO2000003596A1 true WO2000003596A1 (fr) 2000-01-27

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PCT/EP1999/004745 WO2000003596A1 (fr) 1998-07-18 1999-07-07 Utilisation de o-alkyle-carbamates substitues pour lutter contre des parasites animaux

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AU (1) AU5032999A (fr)
DE (1) DE19832444A1 (fr)
WO (1) WO2000003596A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111153832A (zh) * 2020-01-20 2020-05-15 广州九植医药科技有限公司 一种西那卡塞杂质的制备方法

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Publication number Priority date Publication date Assignee Title
DE2637395A1 (de) * 1975-08-22 1977-02-24 Ciba Geigy Ag Neue carbamate
EP0072475A2 (fr) * 1981-08-17 1983-02-23 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Carbamates, procédé de préparation, compositions pesticides et utilisation, à usage pesticide, de ces composés
EP0169169A2 (fr) * 1984-07-18 1986-01-22 Sandoz Ag Composés aromatiques
JPH03258743A (ja) * 1990-03-07 1991-11-19 Nippon Soda Co Ltd エーテル結合を有する化合物、その製造方法及び殺虫剤
EP0584046A1 (fr) * 1992-08-20 1994-02-23 Ciba-Geigy Ag Dérivés d'amide carbamique et leur application comme pesticides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2637395A1 (de) * 1975-08-22 1977-02-24 Ciba Geigy Ag Neue carbamate
EP0072475A2 (fr) * 1981-08-17 1983-02-23 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Carbamates, procédé de préparation, compositions pesticides et utilisation, à usage pesticide, de ces composés
EP0169169A2 (fr) * 1984-07-18 1986-01-22 Sandoz Ag Composés aromatiques
JPH03258743A (ja) * 1990-03-07 1991-11-19 Nippon Soda Co Ltd エーテル結合を有する化合物、その製造方法及び殺虫剤
EP0584046A1 (fr) * 1992-08-20 1994-02-23 Ciba-Geigy Ag Dérivés d'amide carbamique et leur application comme pesticides

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* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 199201, Derwent World Patents Index; Class C03, AN 1992-004464, XP002119855 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111153832A (zh) * 2020-01-20 2020-05-15 广州九植医药科技有限公司 一种西那卡塞杂质的制备方法
CN111153832B (zh) * 2020-01-20 2022-02-25 广州九植医药科技有限公司 一种西那卡塞杂质的制备方法

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DE19832444A1 (de) 2000-01-20

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