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WO1995019351A1 - Derives d'aryl-5-methylene-oxazole - Google Patents

Derives d'aryl-5-methylene-oxazole Download PDF

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Publication number
WO1995019351A1
WO1995019351A1 PCT/EP1995/000019 EP9500019W WO9519351A1 WO 1995019351 A1 WO1995019351 A1 WO 1995019351A1 EP 9500019 W EP9500019 W EP 9500019W WO 9519351 A1 WO9519351 A1 WO 9519351A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
substituted
optionally
formula
Prior art date
Application number
PCT/EP1995/000019
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German (de)
English (en)
Inventor
Udo Kraatz
Ulrike Wachendorff-Neumann
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 EP95905116A priority Critical patent/EP0740662A1/fr
Priority to JP7518804A priority patent/JPH09507491A/ja
Priority to AU13855/95A priority patent/AU1385595A/en
Publication of WO1995019351A1 publication Critical patent/WO1995019351A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Definitions

  • the invention relates to new aryl-5-methylene-oxazole derivatives, a process for their preparation and their use for controlling animal pests.
  • R 1 represents alkyl or optionally substituted alyl
  • R 2 represents alkyl or optionally substituted phenyl, phenylalkyl, phenylalkenyl, phenoxyalkyl and phenylthioalkyl; or
  • R 1 and R 2 together represent doubly linked, optionally substituted or fused alkanediyl, where one or two non-adjacent CH 2 groups are optionally replaced by O and / or S;
  • R 3 represents halogen, alkyl or alkoxy
  • R 4 represents halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio and
  • R, 1, R ⁇ 2, R r> 3, R ⁇ 4 and n have the meaning given above,
  • aryl-5-methylene-oxazole derivatives of the formula (I) are very suitable for controlling animal pests. They are particularly characterized by their high effectiveness against arthropods and nematodes.
  • the aryl-5-methylene-oxazole derivatives of the formula (I) according to the invention show a high activity against animal pests.
  • the compounds according to the invention are generally defined by the formula (I).
  • R 1 is preferably C j -C 8 alkyl or phenyl which is optionally mono- to pentasubstituted by halogen, the same or different,
  • R 2 is preferably C j -C 6 - alkyl, or represents in each case optionally mono- to tetrasubstituted by identical or different substituents, phenyl, benzyl, pheneth-1-yl, pheneth-2-yl, phenoxymethyl,
  • haloalkyl substituted pyridyloxy each through single to triple, the same or different C j -C 12 alkyl, halogen, C ⁇ haloalkyl, CC 8 alkoxy, C ] -C 6 haloalkoxy, CC 8 alkoxy-C j -C ß alkyl, C - C 6 alkoxy -ethyleneoxy, C j -C 6 alkyl thio and / or C 1 -C 6 haloalkylthio substituted phenyl, benzyl, phenoxy, phenylthio, benzyloxy and benzylthio, or
  • R 1 and R 2 together preferably represent double-linked, optionally one to four times, identically or differently substituted 2- to 6-membered, optionally benzanellated alkanediyl, optionally one or two non-adjacent CH 2 groups by O and / or S are replaced, and suitable substituents: C j -C 4 -alkyl, in each case optionally mono- to tetrasubstituted by identical or different substituents, phenyl or a fused-on benzo, wherein each of the substituents mentioned in connection with the definition of R 2 is phenyl as a substituent come into question.
  • R 3 preferably represents fluorine, chlorine, bromine, C j -C 4 alkyl or C j -C 4 alkoxy.
  • R 4 preferably represents fluorine, chlorine, bromine, C j -C 4 alkyl, C j -C 4 alkoxy, C j - C 4 alkylthio, C 1 -C 4 haloalkyl, C ] -C 4 haloalkoxy or C ] -C 4 haloalkylthio.
  • n is preferably a number 0.1, 2, 3 or 4.
  • R 1 particularly preferably represents C ] -C 4 -alkyl or phenyl, which is optionally mono- to pentasubstituted, identically or differently, by F, Cl, Br, C r C 4 -alkyl, C r C 3 -alkoxy , C r C 3 alkylthio which is monosubstituted to pentasubstituted by identical or different F and / or Cl-substituted C j -C-j alkyl, mono- to pentasubstituted by identical or different F and / or Cl substitu ⁇ jewes C r C 4 -alkoxy, SCF 3 or SCHF 2 .
  • R 2 particularly preferably represents C j -C 4 -alkyl or represents in each case optionally mono- to tetrasubstituted by identical or different substituents, phenyl, benzyl, Pheneth- 1-yl, pheneth-2-yl, phenoxymethyl, phenylthiomethyl, phenoxy eth- 1 - yl, phenoxyeth-2-yl or stryryl, each of which may be mentioned as a phenyl substituent F, Cl, Br, C, -C 18 alkyl, C r C 6 alkoxy-C r C 8 alkyl ; mono- to hexasubstituted by identical or different F and / or Cl sub- stitutechnischs C j -C 8 -alkoxy which is monosubstituted to pentasubstituted by identical or different F and / or Cl sub ⁇ stitutechnischs CC 2 alkyl,
  • C j -C jj alkyl F, Cl, Br, CF 3 , CC 4 alkoxy, simple to sixfold, identical or differently substituted by F and / or Cl, C j -C 4 alkoxy, CC 4 - alkoxy-C j -C 4 alkyl, C j -C 4 -alkoxy-ethyleneoxy, C j -C 4 -alkylthio which is monosubstituted to hexasubstituted by identical or different F and / or Cl-substituted C -, - C 4 - alkylthio-substituted phenyl, Benzyl, phenoxy, phenylthio, benzyloxy and
  • R 2 together are particularly preferably double-linked, optionally mono- to tetrasubstituted, identically or differently substituted 2- to 6-membered, optionally benzanellated alkanediyl, optionally one or two non-adjacent CH 2 groups being replaced by O and / or S. and are suitable substituents: C j -C 4 -alkyl and in each case optionally mono- to tetrasubstituted by identical or different substituents, phenyl or a fused benzo group, wherein in each case as substituents in question substituents mentioned for phenyl 2 in connection with the definition of R come .
  • R 3 particularly preferably represents fluorine, chlorine, methyl or methoxy.
  • R 4 particularly preferably represents fluorine, chlorine, C, -C 3 -alkyl, C j -C 3 -alkoxy, CC 3 -alkylthio, mono- to quintuple, identical or different, substituted by fluorine and or chlorine, C 1 -C 3 - Alkyl, single to quintuple, identical or different C j -, - alkoxy, SCF 3 and SCHF 2 substituted by fluorine and / or chlorine.
  • n particularly preferably represents a number 0, 1, 2, 3 or 4.
  • radicals R 4 may be the same or different for n> 1.
  • R 1 represents methyl, ethyl, n-propyl, i-propyl, phenyl or 4-chlorophenyl,
  • R represents methyl, ethyl, n-propyl, i-propyl or phenyl or benzyl, which are substituted by one of the substituents R listed in Table 1 below and
  • R 1 and R 2 together with the carbon atom to which they are attached represent a cyclopentyl or cyclohexyl radical.
  • the compounds of the formula (I) can be in the form of geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates to both the pure isomers and the isomer mixtures.
  • hydrocarbon radicals mentioned above in the definition of the compounds according to the invention are in each case straight-chain or branched as far as possible, even in conjunction with heteroatoms, such as alkoxy.
  • Formula (II) provides a general definition of the benzamides to be used as starting materials in process a) for the preparation of the compounds of the formula (I).
  • R 1 , R 2, R 3 , R 4 and n preferably or particularly preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as were particularly preferably indicated for R 1 , R 2, R 3 , R 4 and n.
  • R 1 represents alkyl or optionally substituted aryl
  • R represents alkyl or optionally substituted phenyl, phenylalkyl
  • R 3 represents halogen, alkyl or alkoxy
  • R 4 represents halogen, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or
  • n stands for a number 0, 1, 2, 3 or 4
  • R 3 , R 4 and n have the meaning given above,
  • the benzoyl chlorides of the formula (III) and the propargylamines of the formula (IV) are generally known compounds and / or can be prepared in a simple manner by known methods.
  • the process according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a diluent.
  • Suitable diluents for carrying out the process according to the invention are all customary inert organic solvents.
  • Aliphatic, alicyclic or aromatic hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, petroleum ether, hexane, ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethyl englykoldimethyl or - di ethyl ether; Amides such as N, N-dimethylformamide and N, N-dimethylacetamide, N-
  • Methyl pyrrolidone or hexamethyl phosphoric acid triamide Methyl pyrrolidone or hexamethyl phosphoric acid triamide.
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 20 ° C and 120 ° C, preferably at temperatures between 40 ° C and 100 ° C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the process according to the invention is preferably carried out in the presence of a base. All common inorganic or organic bases come in here
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, are preferably usable.
  • DABCO Diazabicyclooctane
  • DBN diazabicyclonones
  • DBN diazabicycloundecene
  • the benzamides of the formula (II) required in each case are reacted with 0.1 to 80 mol%, preferably 1-50 mol% and in particular 1-20 mol% of the base.
  • 0.1 to 80 mol% preferably 1-50 mol% and in particular 1-20 mol% of the base.
  • the active substances are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • animal pests preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura for example Lepisma saccharina.
  • Collembola for example Onychiurus armatus.
  • Orthoptera e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Cheimatobia brumata Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplocapsa n.
  • Conoderus spp. Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium 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., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
  • Plant-parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp ..
  • the substances of the formula (I) according to the invention also have a fungicidal activity.
  • the active ingredients can be converted into the usual formulations, such as
  • Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances and in coating compositions for seeds, furthermore in formulations with Fuel sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and Wa ⁇ nnebel formulations.
  • formulations are produced known manner in b e, for example by mixing the active compounds with extenders, that is liquid solvents and / or solid carriers, optionally with the use of surfactants, that is emulsifiers and / or dispersants and / or foam-forming 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 or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • 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 dimethylformamide and dimethyl sulfoxide, and water; with liquefied gaseous extenders or carriers are such
  • Liquids are meant which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide;
  • Possible solid carriers are: for example 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;
  • Solid carriers for granules are possible: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco sticks;
  • Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also 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 are used.
  • 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 are used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from the formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Demeton M Demeton-S-methyl, Demeton S, Diazinon, Dichlorvos, Dicliphos, Dichlorfenthion, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxathion, Disulfoton, Edifenphos, Ethion, Etrimphos, Fenitrothion, Fenthion, Fonophos, Isothophophos, Hepthosphate, Hepten Isoxathion, Phorate, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Methacrifos, Methamidophos, Naled, Omethoate, Oxydemeton M, Oxydeprofos, Parathion A, Parathion M, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Moxim, Pirimhiphiphiphiros Prothiophos
  • 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 connections through which the
  • 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 compounds according to the invention act not only against plant, hygiene and stored product pests, but also in the veterinary sector against animal parasites (ectoparasites and endoparasites) such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings, fleas and endoparasitic worms.
  • animal parasites ectoparasites and endoparasites
  • tick ticks such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings, fleas and endoparasitic worms.
  • tick ticks such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings, fleas and endoparasitic worms
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Hamsters, guinea pigs, rats and
  • 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, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • 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.
  • 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 cabbage cockroach (Plutella maculipennis) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • 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.
  • Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with larvae of the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
  • the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • compound 2 of the preparation examples with an exemplary active compound concentration of 0.1%, causes a degree of killing of 100% after 6 days.
  • Emulsifier 35 parts by weight of nonylphenol polyglycol ether

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention a pour objet de nouveaux dérivés d'aryl-5-méthylène-oxazole de formule (I), dans laquelle R1 désigne un alkyle ou un aryle éventuellement substitué, R2 désigne un alkyle, ou un phényle, phénylalkyle, phénylalkényle, phénoxyalkyle et phénylthioalkyle, chacun de ces groupes étant éventuellement substitué, R1 et R2 désignent ensemble un alcane-diyle lié deux fois, éventuellement substitué ou annelé, où éventuellement un ou deux groupes CH¿2? non voisins sont remplacés par O et/ou S, et R?3¿ désigne un halogène, un alkyle ou un alkoxy, R4 désigne un halogène, un alkyle, alkoxy, alkylthio, halogénure d'alkyle, halogénure d'alkoxy ou halogénure d'alkylthio, et n est un nombre égal à 0, 1, 2, 3 ou 4, un procédé pour leur fabrication, de nouveaux produits intermédiaires de formule (II), ainsi que l'utilisation des composés de formule (I) comme parasiticides.
PCT/EP1995/000019 1994-01-17 1995-01-04 Derives d'aryl-5-methylene-oxazole WO1995019351A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP95905116A EP0740662A1 (fr) 1994-01-17 1995-01-04 Derives d'aryl-5-methylene-oxazole
JP7518804A JPH09507491A (ja) 1994-01-17 1995-01-04 アリール−５−メチレン−オキサゾール誘導体
AU13855/95A AU1385595A (en) 1994-01-17 1995-01-04 Aryl-5-methylene-oxazole derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944401100 DE4401100A1 (de) 1994-01-17 1994-01-17 Aryl-5-methylen-oxazol-Derivate
DEP4401100.8 1994-01-17

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WO1995019351A1 true WO1995019351A1 (fr) 1995-07-20

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JP (1) JPH09507491A (fr)
AU (1) AU1385595A (fr)
DE (1) DE4401100A1 (fr)
WO (1) WO1995019351A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0879819A1 (fr) * 1997-05-21 1998-11-25 Rohm And Haas Company Procédé pour la préparation de 5-méthylène-oxazolines
US5859254A (en) * 1997-04-15 1999-01-12 Rohm And Haas Company Process to chloroketones using oxazolines
EP0952143A1 (fr) * 1998-04-21 1999-10-27 Rohm And Haas Company Procédé de préparation d'oxazolines catalysé par un sel métallique et préparation ultérieure de chlorocétones

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3745168A (en) * 1971-12-03 1973-07-10 Rohm & Haas 5-alkoxy-5-chloromethloxazolines
EP0553623A1 (fr) * 1992-01-28 1993-08-04 Sumitomo Chemical Company, Limited Dérivés d'oxazoline, leur production et leur utilisation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3745168A (en) * 1971-12-03 1973-07-10 Rohm & Haas 5-alkoxy-5-chloromethloxazolines
EP0553623A1 (fr) * 1992-01-28 1993-08-04 Sumitomo Chemical Company, Limited Dérivés d'oxazoline, leur production et leur utilisation

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* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 74, no. 21, 24 May 1971, Columbus, Ohio, US; abstract no. 110686p, YIH, R.; SWITHENBANK, C.: "Identification of metabolites of N-(1,1-dimethyl-propynyl)-3,5-dichlorobenzamide in soil and alfalfa" page 299; *
J. AGR. FOOD CHEM., vol. 19, no. 2, 1971, pages 319 - 324 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5859254A (en) * 1997-04-15 1999-01-12 Rohm And Haas Company Process to chloroketones using oxazolines
US5936096A (en) * 1997-04-15 1999-08-10 Rohm And Haas Company Process to chloroketones using oxazolines
EP0872474A3 (fr) * 1997-04-15 2002-01-02 Rohm And Haas Company Procédé pour la préparation de chloro-cétones à partir d'oxazolines
EP0879819A1 (fr) * 1997-05-21 1998-11-25 Rohm And Haas Company Procédé pour la préparation de 5-méthylène-oxazolines
US6147220A (en) * 1997-05-21 2000-11-14 Rohm And Haas Company Process to 5-methyleneoxazolines
EP0952143A1 (fr) * 1998-04-21 1999-10-27 Rohm And Haas Company Procédé de préparation d'oxazolines catalysé par un sel métallique et préparation ultérieure de chlorocétones
US6057477A (en) * 1998-04-21 2000-05-02 Rohm And Haas Company Metal salt catalyzed process to oxazolines and subsequent formation of chloroketones

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DE4401100A1 (de) 1995-07-20
JPH09507491A (ja) 1997-07-29
AU1385595A (en) 1995-08-01

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