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WO1997019051A1 - Amides d'acide fluorobutenoyloxyacetique - Google Patents

Amides d'acide fluorobutenoyloxyacetique Download PDF

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Publication number
WO1997019051A1
WO1997019051A1 PCT/EP1996/004824 EP9604824W WO9719051A1 WO 1997019051 A1 WO1997019051 A1 WO 1997019051A1 EP 9604824 W EP9604824 W EP 9604824W WO 9719051 A1 WO9719051 A1 WO 9719051A1
Authority
WO
WIPO (PCT)
Prior art keywords
spp
formula
compounds
alkyl
preparation
Prior art date
Application number
PCT/EP1996/004824
Other languages
German (de)
English (en)
Inventor
Udo Kraatz
Wolfram Andersch
Christoph Erdelen
Andreas Turberg
Norbert Mencke
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 AU75653/96A priority Critical patent/AU7565396A/en
Priority to JP9519331A priority patent/JP2000500473A/ja
Priority to EP96938093A priority patent/EP0861227A1/fr
Priority to BR9611733A priority patent/BR9611733A/pt
Publication of WO1997019051A1 publication Critical patent/WO1997019051A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms

Definitions

  • the present invention relates to new fluorobutenoyloxyacetic acid amides, processes for their preparation and their use for combating animal
  • Pests especially insects, arachnids and nematodes, which protect in agriculture, in the forest, in the supply and material and in the hygiene sector
  • R 1 represents hydrogen or halogen
  • R 2 represents hydrogen, alkyl or optionally substituted aryl
  • R 3 and R 4 independently of one another represent hydrogen, alkyl, alkenyl, cycloalkyl, alkoxy or in each case optionally substituted aryi or hetaryl,
  • R J and R 4 together represent alkanediyl or -CH 2 -CH 7 -X-CH 9 -CH 0 -,
  • X represents oxygen, sulfur or NR 5 and
  • R s represents hydrogen, alkyl or optionally substituted aryl
  • the compounds of the formula (I) can exist as geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates to both the pure isomers and the isomer mixtures
  • R 2 , R and R 4 have the meaning given above,
  • R preferably represents hydrogen, fluorine or chlorine
  • R 2 preferably represents hydrogen, C r C 6 alkyl or optionally single to triple, identical or different by halogen, C j -C 6 alkyl! or C ] -C 6 alkoxy substituted phenyl.
  • R 3 and R 4 independently of one another preferably represent hydrogen, C, -C 6 alkyl, C 2 -C ] 0 alkenyl, C 4 -C 8 cycloalkyl, CT-Q-alkoxy, optionally by fluorine, chlorine, bromine , Nitro, cyano, C, -C 6 alkyl, C, -C 6 haloalkyl, C, - C 6 alkoxy, C j -C ⁇ haloalkoxy, C r C 6 alkylthio or C, -C 6 halo alkylthio-substituted phenyl, optionally substituted by fluorine, chlorine or C 1 -C 4 -alkyl, hetaryl with 5 or 6 ring atoms and one or two heteroatoms from the series nitrogen, oxygen and sulfur,
  • R 3 and R 4 stand together for C 4 - C g - AI kandiy 1 or for
  • X represents oxygen, sulfur or NR 5 ,
  • R is preferably hydrogen, C j -C 8 alkyl or optionally substituted by fluorine, chlorine, bromine or C, -C 6 alkyl substituted phenyl
  • R 1 particularly preferably represents hydrogen or fluorine
  • R ⁇ particularly preferably represents hydrogen or C ] -C 4 -alkyl
  • R 'and R 4 independently of one another particularly preferably represent hydrogen, C, -C 4 alkyl, C 3 -C 8 alkenyl, C 3 -C 6 cycloalkyl, C, -C 2 alkoxy, optionally by fluorine , Chlorine, C, -C 4 alkyl or C r C 4 alkoxy substituted phenyl or for pyridyl, furanyl or thienyl,
  • R 3 and R 4 stand together for or for -CH 2 -CH 2 -X-CH 2 -CH 2 -,
  • X represents oxygen, sulfur or NR 5
  • R 5 particularly preferably represents hydrogen, C, -C 4 -alkyl or phenyl which is optionally substituted by fluorine, chlorine, bromine or C r C 4 -alkyl
  • R 1 particularly stands for hydrogen or fluorine
  • R 3 and R 4 independently of one another are particularly emphasized for hydrogen, methyl, ethyl !, propyl, i-propyl, methoxy, ethoxy, allyl, optionally phenyl or substituted by fluorine or chlorine
  • R 3 and R 4 together represent C 5 - or C 6 -alkanedyl
  • CF 2 CF-CH 2 -COCl + HO-CH 2 -CO-N (C 4 H 9 ) 2
  • (I) is characterized in that hydroxy acetic amides of the formula (II) are reacted with acid chlorides of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of a base
  • the process according to the invention is preferably carried out in the presence of a diluent
  • Suitable diluents are, in particular, organic solvents, for example optionally chlorinated aliphatic or aromatic hydrocarbons such as cyelohexane, toluene, xylene, dichloromethane, dichloroethane, chloroform or chlorobenzene, ethers such as diethyl ether, dioxane or tetrahydrofuran or nitriles such as acetonitrile
  • Amines are preferably used, in particular tertiary amines such as triethylamine, diazabicycloundecene (DBU), diazabicyclonones (DBN), diazabicycloctane (DABCO) or pyridine or alkali metal or alkaline earth metal carbonates, hydrogen carbonates or hydroxides.
  • tertiary amines such as triethylamine, diazabicycloundecene (DBU), diazabicyclonones (DBN), diazabicycloctane (DABCO) or pyridine or alkali metal or alkaline earth metal carbonates, hydrogen carbonates or hydroxides.
  • Examples include sodium carbonate, potassium carbonate, Sodium bicarbonate, sodium hydroxide, potassium hydroxide and calcium hydroxide are called
  • the reaction temperature can be varied within a wide range. In general, temperatures between -20 ° C and 180 ° C, preferably between 0 ° C and 120 ° C
  • the molar ratio of the compound of formula (II) to the compound of formula (III) is generally 3 1 to 1 3, preferably 1.5 1 to 1 1, 5
  • the reaction is generally carried out under normal pressure
  • reaction mixture is hydrolyzed and the product is extracted with an organic solvent such as ethyl acetate, dichloromethane or toluene
  • hydroxyacetic acid amides of the formula (II) required as starting materials are known and / or can be prepared in a simple manner by known methods
  • the active substances are suitable for controlling animal pests, in particular insects, arachnids and nematodes which occur in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are sensitive to normal and resistant species and effective against all or individual development cities
  • the pests mentioned above include
  • Orthoptera e.g. Blatta orientalis, Pe ⁇ planeta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp, Locusta migrato ⁇ a migrato ⁇ oides, Melanoplus differentialis, Schistocerca grega ⁇ a
  • Thysanoptera for example Hercinothrips femorahs, Thrips tabaci
  • Heteroptera e.g. Eurygaster spp, Dysdercus intermedius, Piesma quadrata, Cimex lectulanus, Rhodmus prohxus, Tnatoma spp
  • Hymenoptera From the order of the Hymenoptera, for example Diprion spp, Hoplocampa spp, Lasius spp, Monomo ⁇ um pharaonis, Vespa spp
  • Drosophila melanogaster Musca spp, Fannia spp, Calliphora erythrocephala, Lucilia spp, Chrysomyia spp, Cuterebra spp, Gastrophilus spp, Hyppobosca spp, Stomoxys spp, Oestrus spp, Hypoderma spp, Tabanus spp, Tanniaulppia sppanppella hppiappella, Bibio , Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa
  • the plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus similis, D ⁇ t ⁇ lenchus dipsaci, Tylenchulus semipenetrans Heterodera spp, Globodera spp, Meloidogyne spp, Aphelenchoides spp, Longidorus spp, Xiphinema spp, T ⁇ chodorus spp
  • the compounds of the formula (1) according to the invention are notable in particular for an excellent nematicidal action, for example against Meloidogyne incognita
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, powdered powders, suspensions, powders, dusting agents, pastes, loose powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances
  • formulations are prepared in a known manner, for example 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
  • Aromatic compounds such as xylene, toluene or are essentially suitable as liquid solvents
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyelohexane or paraffins, eg 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 cyelohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water
  • Solid carrier materials that come into question are, for example, ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmole lumps or diatomaceous earth and synthetic rock powders, such as highly disperse silica and alumina Silicates, as solid carriers for granulates are possible: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; come in as emulsifying and / or foaming agents
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite 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, such as cephalins and lecithins and synthetic 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, boron, 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 ingredient according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active ingredients, such as insecticides, attractants, stanlants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active ingredients such as insecticides, attractants, stanlants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, Phos - phosphoric esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Fungicides 2-aminobutane, 2-anilino-4-methyl-6-cyclopropyl-py ⁇ mid ⁇ n, 2 ', 6'-dibromo-2-methyl-4'-t ⁇ fluoromethoxy-4'-trifluoro-methyl-l, 3- th ⁇ azol-5-carboxanilide, 2, 6-di- chloroN- (4-t ⁇ fluoromethylbenzyl) -benzam ⁇ d, (E) -2-methoxy ⁇ m ⁇ no-N-methyl-2- (2-phenoxyphenyl) -acetam ⁇ d, 8-Hydroxyqu ⁇ nohnsulfat, methyl- (E) -2- ⁇ 2- [6- (2-cyano-phenoxy) -py ⁇ m ⁇ d ⁇ n-4-yloxy] -phenyl ⁇ -3-methoxyacrylate, methyl- (E) -methox ⁇ m ⁇ no- [alpha- (o-tolyloxy) -o-to
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb Fenothiocarb, Fenoxycarb, Fenpropath ⁇ n, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate,
  • Fipronil Fluazinam, Flucycloxuron, Flucyth ⁇ nat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox,
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhaloth ⁇ n, Lufenuron,
  • Tebufenozid Tebufenpyrad, Tebupi ⁇ mphos, Teflubenzuron, Tefluth ⁇ n, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thtofanox, Thio-methon, Thionazin, Thu ⁇ ngiensin, Talomethathonon, Talomethathonon, Talomethathonon XMC, Xylylcarb, YI 5301/5302, Zetameth ⁇ n
  • 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 by which the action of the active compounds 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 application takes place in a customary manner adapted to the application forms
  • the active ingredient When used against hygiene and storage damage, the active ingredient is characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates
  • the active compounds according to the invention act not only against plant, hygiene and supply damage, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks and mites Running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas
  • animal parasites ectoparasites
  • ectoparasites such as tick ticks, leather ticks and mites
  • Anoplu ⁇ da for example Haematopinus spp, Lmognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp
  • Hyalomma spp Hyalomma spp, Rhipicephalus spp, Dermanyssus spp, Railhetia spp, Pneu- monyssus spp, Sternostoma spp, Varroa spp
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are agricultural livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese , Bees, other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • arthropods are agricultural livestock, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese , Bees, other domestic animals such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinks, drenches, granules, pastes, Boh, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the aid of shaped bodies containing active ingredients, such as collars, ear tags, tail tags, ghedma tapes, holsters, marking devices, etc
  • the active compounds of the formula (I) can be formulated (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath
  • CF 2 CF-CH 2 -CO-0-CH 2 -CO-N (nC 4 H 9 ) 2
  • the active ingredient preparation is intimately mixed with soil that is heavily contaminated with the test nematodes.
  • the concentration of the active ingredient in the preparation is practically irrelevant.
  • the treated soil is filled into pots, sat lettuce and the pots are kept at a greenhouse temperature of 25 ° C
  • the lettuce roots are examined for nematode infestation (root galls) and the degree of effectiveness of the active ingredient is determined in%.
  • the degree of effectiveness is 100% if the infestation is avoided completely, it is 0% if the infestation is exactly as high as that of the Control plants in untreated but easily contaminated soil
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochleariae) while the leaves are still moist
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella macuhpennis) while the leaves are still moist
  • Rice seedlings (Oryzae sativa) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist
  • Test animals adult sucked females
  • the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid.
  • the compounds according to Preparation Examples 1, 2, 3, 4, 5 and 6 had an activity of 100% at an exemplary active ingredient concentration of 20 ⁇ g / animal.
  • a suitable formulation three parts by weight of active ingredient are mixed with seven parts of the solvent / emulsifier mixture mentioned above, and the emulsion concentrate thus obtained is diluted with water to the concentration desired in each case.
  • the criterion for the effect is the occurrence of death in the treated larvae after 48 h (larvicidal effect), or the inhibition of Aduit hatching from the pupa or the inhibition of pupa formation.
  • the criterion for the m-vitro effect of a substance is the inhibition of Flea development, or a development standstill before the adult stage. 100% larvicidal activity means that after 48 hours all larvae have died. 100% development-inhibitory effect means that no adult flies have hatched

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouveaux amides d'acide fluorobuténoyloxyacétique de la formule (I) où R?1, R2, R3 et R4¿ ont la signification donnée dans la description. L'invention concerne également leur procédé de production et leur utilisation dans la lutte contre les animaux parasites.
PCT/EP1996/004824 1995-11-17 1996-11-05 Amides d'acide fluorobutenoyloxyacetique WO1997019051A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU75653/96A AU7565396A (en) 1995-11-17 1996-11-05 Fluorobutenoyloxyacetamides
JP9519331A JP2000500473A (ja) 1995-11-17 1996-11-05 フルオロブテノイルオキシアセトアミド
EP96938093A EP0861227A1 (fr) 1995-11-17 1996-11-05 Amides d'acide fluorobutenoyloxyacetique
BR9611733A BR9611733A (pt) 1995-11-17 1996-11-05 Fluorobutenoiloxiacetamidas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19542935.4 1995-11-17
DE1995142935 DE19542935A1 (de) 1995-11-17 1995-11-17 Fluorbutenoyloxyessigsäureamide

Publications (1)

Publication Number Publication Date
WO1997019051A1 true WO1997019051A1 (fr) 1997-05-29

Family

ID=7777742

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1996/004824 WO1997019051A1 (fr) 1995-11-17 1996-11-05 Amides d'acide fluorobutenoyloxyacetique

Country Status (6)

Country Link
EP (1) EP0861227A1 (fr)
JP (1) JP2000500473A (fr)
AU (1) AU7565396A (fr)
BR (1) BR9611733A (fr)
DE (1) DE19542935A1 (fr)
WO (1) WO1997019051A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000071500A1 (fr) * 1999-05-19 2000-11-30 Bayer Aktiengesellschaft Composes halogene

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102014224491A1 (de) 2014-12-01 2016-06-02 Continental Reifen Deutschland Gmbh Mittel zum provisorischen Abdichten von aufblasbaren oder aufpumpbaren Gegenständen und Verfahren zum provisorischen Abdichten von aufblasbaren oder aufpumpbaren Gegenständen
DE102019219082A1 (de) 2019-12-06 2021-06-10 Continental Reifen Deutschland Gmbh Verfahren zum Recycling von Fahrzeugluftreifen mit Dichtmittellage

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4950666A (en) * 1989-03-30 1990-08-21 Fmc Corporation Difluoroalkane and difluoroalkenylalkane pesticides
EP0432861A1 (fr) * 1989-12-15 1991-06-19 Schering Aktiengesellschaft Oléfines halogénées, procédé pour leur préparation et leur utilisation comme pesticides
WO1992015555A2 (fr) * 1991-03-01 1992-09-17 Monsanto Company Composes fluoroalcenyles et utilisation de ces composes comme insecticides
EP0577555A1 (fr) * 1992-06-30 1994-01-05 Ciba-Geigy Ag Dérivés d'acides carboxyliques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4950666A (en) * 1989-03-30 1990-08-21 Fmc Corporation Difluoroalkane and difluoroalkenylalkane pesticides
EP0432861A1 (fr) * 1989-12-15 1991-06-19 Schering Aktiengesellschaft Oléfines halogénées, procédé pour leur préparation et leur utilisation comme pesticides
WO1992015555A2 (fr) * 1991-03-01 1992-09-17 Monsanto Company Composes fluoroalcenyles et utilisation de ces composes comme insecticides
EP0577555A1 (fr) * 1992-06-30 1994-01-05 Ciba-Geigy Ag Dérivés d'acides carboxyliques

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000071500A1 (fr) * 1999-05-19 2000-11-30 Bayer Aktiengesellschaft Composes halogene

Also Published As

Publication number Publication date
JP2000500473A (ja) 2000-01-18
EP0861227A1 (fr) 1998-09-02
BR9611733A (pt) 1999-02-23
AU7565396A (en) 1997-06-11
DE19542935A1 (de) 1997-05-22

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