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WO1996041534A1 - Utilisation d'oxazolines pour lutter contre les ectoparasites - Google Patents

Utilisation d'oxazolines pour lutter contre les ectoparasites Download PDF

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Publication number
WO1996041534A1
WO1996041534A1 PCT/EP1996/002284 EP9602284W WO9641534A1 WO 1996041534 A1 WO1996041534 A1 WO 1996041534A1 EP 9602284 W EP9602284 W EP 9602284W WO 9641534 A1 WO9641534 A1 WO 9641534A1
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WO
WIPO (PCT)
Prior art keywords
spp
formula
optionally
alkyl
acid
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP1996/002284
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German (de)
English (en)
Inventor
Norbert Mencke
Andreas Turberg
Udo Kraatz
Wolfgang Krämer
Reinhard Lantzsch
Albrecht Marhold
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Yashima Chemical Industrial Co Ltd
Original Assignee
Bayer AG
Yashima Chemical Industrial Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG, Yashima Chemical Industrial Co Ltd filed Critical Bayer AG
Priority to BR9609252A priority Critical patent/BR9609252A/pt
Priority to EP96916163A priority patent/EP0831704A1/fr
Priority to JP9502549A priority patent/JP2000501695A/ja
Priority to AU59020/96A priority patent/AU5902096A/en
Priority to SK1662-97A priority patent/SK166297A3/sk
Publication of WO1996041534A1 publication Critical patent/WO1996041534A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • 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
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • the present invention relates to the use of oxazolines for controlling ectoparasites and to ectoparasiticidal compositions which contain oxazolines.
  • Oxazolines and their production and use as insecticides and acaricides in crop protection and against certain mites on animals are already known. However, nothing is known about their use against ectoparasites and, above all, against insects and host ticks.
  • the present invention relates to the use of compounds of the formula (I)
  • B represents optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl,
  • A represents aryl, aryloxy, heteroaryl, heteroaryloxy which are optionally substituted and which are optionally bonded to the oxazoline ring via a divalent radical Z,
  • R stands for hydrogen or together with A and the adjacent C atom for a spirocyclic 3- to 6-membered ring which may optionally contain one or more heteroatoms of the group O, S, N and to which another ring may be fused, where the system is optionally substituted,
  • the compounds of the formula (I) are, for example, the subject of the following patent applications: WO 93/21 165, WO 93/24470, JP-OS H4 89 484, JP-OS H6 145 155, JP-OS H6 145 169, JP-OS H6 100 546; JP-OS H6 100 560, JP-OS H6 73 030, EP-OS 345 775, EP-OS 432 661, EP-OS 553 623, WO 93/22 297, WO 93/25 079.
  • Optionally substituted alkyl alone or as part of a radical in the general formulas means straight-chain or branched alkyl having preferably 1 to 20, in particular 1 to 18, carbon atoms. Exemplified and preferred are optionally substituted methyl, ethyl, n- and i-propyl, n-, i- and t-butyl, neopentyl, undecyl, dodecyl, pentadecyl, octadecyl.
  • Optionally substituted alkenyl and the alkenyl portion of a residue such as e.g. optionally substituted alkenyloxy and alkenylthio in general
  • Formulas mean straight-chain or branched alkenyl with preferably 2 to 6, in particular 2 to 4, carbon atoms.
  • exemplary and preferably, optionally substituted ethenyl, propenyl (1), propenyl (2) and butenyl (3) may be mentioned.
  • Optionally substituted alkynyl and the alkynyl portion of a residue such as e.g. optionally substituted alkynyloxy and alkynylthio in the general formulas mean straight-chain or branched alkynyl having preferably 2 to 6, in particular 2 to 4, carbon atoms.
  • Substituted ethynyl, propynyl (1), propynyl (2) and butynyl (3) may be mentioned by way of example and in preference.
  • Optionally substituted cycloalkyl alone or as part of a radical in the general formulas means mono-, bi- and tricyclic cycloalkyl with preferably 3 to 10, in particular 3, 5 or 6 carbon atoms. Examples and preferably, optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl may be mentioned.
  • Optionally substituted alkoxy alone or as part of a radical in the general formulas means straight-chain or branched alkoxy with preferably 1 to 6, in particular 1 to 4, carbon atoms. Exemplified and preferred are optionally substituted methoxy, ethoxy, n- and i-propoxy and n-, o- and t-butoxy.
  • Optionally substituted alkylthio alone or as part of a radical in the general formulas means straight-chain or branched alkylthio with preferably 1 to 6, in particular 1 to 4, carbon atoms.
  • optionally substituted methylthio, ethylthio, n- and i-propylthio, n-, o- and t-butylthio may be mentioned.
  • Optionally substituted carbalkoxy alone or as part of a radical in the general formulas means straight-chain or branched carbalkoxy with preferably 2 to 7, in particular 2 to 5, carbon atoms.
  • optionally substituted carbomethoxy, carboethoxy, carbo-n- and -i-propyloxy and carbo-n-, -i and -t-butyloxy may be mentioned.
  • Haloalkyl alone or as part of a residue such as e.g. Haloalkoxy or haloalkylthio in the general formulas contains 1 to 4, in particular 1 or 2, carbon atoms and preferably 1 to 5, in particular 1 to 3 identical or different halogen atoms, fluorine, chlorine and bromine, in particular fluorine and chlorine, preferably being halogen atoms.
  • Examples include trifluoromethyl, chlorodifluoromethyl, bromomethyl, 2,2,2-trifluoroethyl and pentafluoroethyl.
  • Optionally substituted aryl alone or as part of a residue such as e.g. Aryloxy, arylthio, arylalkyl in the general formulas preferably means optionally substituted phenyl or naphthyl, in particular phenyl.
  • Optionally substituted aralkyl in the general formulas means optionally substituted aralkyl in the aryl part and / or alkyl part with preferably 6 or 10, in particular 6 carbon atoms in the aryl part (preferably phenyl or naphthyl, in particular phenyl) and preferably 1 to 4, in particular 1 or 2 carbon atoms in the alkyl part , wherein the alkyl part can be straight-chain or branched.
  • Substituted benzyl and phenylethyl may be mentioned as examples and preferably.
  • Optionally substituted heteroaryl alone or as part of a radical such as heteroaryloxy, heteroarylthio, heteroaralkyl means in the general formulas 5- to 7-membered rings with preferably 1 to 3, in particular 1 or 2 identical or different heteroatoms which follow the aromatic principle of the Hückel rule .
  • the heteroatoms are oxygen, sulfur or nitrogen.
  • optionally substituted thienyl may be mentioned.
  • the optionally substituted radicals of the general formula (I) can carry one or more, preferably 1 to 3, in particular 1 to 2 identical or different substituents.
  • B is C j -CG-alkyl which is optionally monosubstituted or polysubstituted by identical or different substituents from halogen, cyano, C 1 -C 4 alkoxy such as so ⁇ through each case optionally mono- to trisubstituted by identical or different halogen , C r C 4 alkyl, C ] -C 4 haloalkyl, C 1 -C 4 alkoxy, C r C 4 haloalkoxy, C 1 -C 4 alkylthio and / or C j -C 4 haloalkylthio substituted phenyl , Phenoxy, benzyloxy, phenylthio and benzylthio;
  • C 3 -C 8 cycloalkyl which is optionally mono- or polysubstituted, identically or differently, by halogen, C r C 4 alkyl, C 2 -C 4 alkenyl, C r C 4 haloalkyl or C 2 -C 4 -
  • C 5 -C 7 cycloalkenyl which is optionally mono- or polysubstituted, identical or different, by halogen, C j -C 4 alkyl or C j - ⁇ haloalkyl;
  • substituents being up to tetrasubstituted by identical or different substi ⁇ tu jewes phenyl are halogen, C r C 4 alkyl, C j -C 4 - alkoxy-C -C 4 alkyl, C j -C 4 -haloalkoxy ,
  • A represents phenyl, benzyl, pheneth-1-yl, pheneth-2-yl, phenoxymethyl, which is optionally monosubstituted to tetrasubstituted or substituted differently,
  • 3,4-tetrafluoroethylene dioxo optionally substituted by C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl and / or halogen benzyliminooxymethyl, each optionally substituted by C r C 6 alkyl, CC 6 - alkoxy, cyclohexyl or phenyl cyclohexyl and cyclohexyloxy; if necessary, single or double, identical or different
  • R preferably represents hydrogen
  • B stands for C j -Cg alkyl, which is optionally mono- or polysubstituted by identical or different substituents
  • C 2 -C 6 alkenyl optionally substituted one or more times, identically or differently, by fluorine, chlorine and / or bromine;
  • C 3 -C 8 cycloalkyl which is optionally mono- or polysubstituted, identical or different, by
  • a and R of the general formula (I) can preferably together form the following spirocyclic rings, which in turn can be substituted, for example, by radicals A:
  • R represents hydrogen or one of the substituents specified for A.
  • X represents hydrogen or halogen.
  • alkanediyl radicals E are preferred:
  • -CH 2 -, -CH (CH 3 ) -, -CH 2 CH 2 -, -CH CH-, -CH 2 O-, -CH 2 S-, -CH (CH 3 ) S-, -CH ( CH 3 ) O-, -CH 2 CH 2 O-, -CH 2 S (O) -, -CH 2 -SO 2 -.
  • X represents a leaving group, such as halogen, alkylsulfonyloxy or arylsulfonyloxy,
  • amino alcohols to be used as starting materials in the process (a) for the preparation of the compounds of the formula (I) are known and / or can be prepared by processes known per se by reducing the corresponding amino acids (cf. Heterocycles 9 (1978), 1277 -1285; J. Org. Chem. 43 (1978), 2539-2541; Liebigs Ann. Chem. 1980, 122-139; Tetrahedron Lett. 26 (1985), 4971-4974).
  • carboxylic acids of the formula (III) to be used further as starting materials in process (a) for the preparation of the compounds of the formula (I) are known organic synthesis chemicals or can be obtained in a known manner.
  • Processes (a) and (b) are carried out using a dehydrating agent.
  • the dehydrating agents common in organic chemistry can be used. Sulfuric acid, polyphosphoric acid (PPS), phosphorus (V) oxide, dicyclohexylcarbodiimide (DCC), phosphorus (V) sulfide and the system triphenylphosphine / triethylamine / tetrachloromethane can preferably be used.
  • organic solvents are suitable as diluents for carrying out processes (a) to (c) according to the invention.
  • Aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, can be used; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide and N, N-dimethylacetamide,
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 10 ° C and 100 ° C.
  • Process (a) 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 starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent in the presence of a dehydrating agent, and the reaction mixture is stirred for several hours at the temperature required in each case. The processing takes place according to usual methods.
  • corresponding nitriles can also be used instead of the carboxylic acids of the formula (III), in which case a catalyst, such as e.g. Zinc (II) chloride is used.
  • a catalyst such as e.g. Zinc (II) chloride is used.
  • the amide alcohols to be used as starting materials in process (b) for the preparation of the compounds of the formula (I) are known and / or can be prepared by processes known per se.
  • the amide alcohols of the formula (IV) are obtained, for example, by acid chlorides derived from the carboxylic acids of the formula (III) with amino alcohols of the formula (II) in the presence of an acid binder, such as triethylamine, pyridine, potassium carbonate, sodium hydroxide or potassium t-butoxide , and in the presence of a diluent such as toluene, chlorobenzene, acetone or acetonitrile, at temperatures between 0 ° C and 100 ° C.
  • an acid binder such as triethylamine, pyridine, potassium carbonate, sodium hydroxide or potassium t-butoxide
  • a diluent such as toluene, chlorobenzene, acetone or acetonitrile
  • the acid chlorides derived from the carboxylic acids of the formula (III) are largely known and / or can be prepared by processes known per se, for example by reacting the carboxylic acids of the formula (III) with a halogenating agent such as thionyl chloride, optionally in the presence of a diluent.
  • a halogenating agent such as thionyl chloride
  • ⁇ -fluoro- ⁇ , ⁇ -dichloro-acrylic acid chloride of the formula (VI) can be obtained by hydrolyzing 2-fluoro-1,3,3,3-pentachloropropene, optionally in the presence of a catalyst.
  • the ⁇ -fluoro- ⁇ , ⁇ -dichloro-acrylic acid chloride formed is optionally partially hydrolyzed to the corresponding acrylic acid, which can then be converted back into the acid chloride, for example by reaction with thionyl chloride.
  • reaction temperatures can be varied within a substantial range when carrying out process (b). In general, temperatures between -20 ° C and + 150 ° C, preferably at temperatures between
  • Process (b) 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.
  • process (b) for the preparation of the compounds of the formula (I) 1 to 20 mol, preferably 1 to 5 mol, of dehydrating agent are generally employed per mole of amide alcohol of the formula (IV).
  • the amide alcohol of the formula (IV) is placed in a diluent and the water-removing agent is then metered in.
  • the reaction mixture is stirred at the required temperature until the end of the reaction and then worked up in the customary manner.
  • amide derivatives to be used as starting materials in process (c) for the preparation of the compounds of the formula (I) are known and / or can be prepared by processes known per se.
  • amide derivatives of the formula (V) are obtained if corresponding amide alcohols of the formula (IV) are used with chlorinating agents, e.g. Thionyl chloride or phosphorus (V) chloride, or with sulfonylating agents, e.g. Methanesulfonic acid chloride or p-toluenesulfonic acid chloride in the usual manner, if appropriate in
  • Process (c) is carried out in the presence of a base.
  • a base All customary inorganic or organic bases can be used. Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates,
  • Acetates, carbonates or bicarbonates such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate , Sodium hydrogen carbonate or ammonium carbonate and also tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundec.
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • reaction temperatures can be varied within a substantial range when carrying out process (c). In general, temperatures between -20 ° C and + 150 ° C, preferably at temperatures between 0 ° C and 100 ° C.
  • Process (c) 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 amide derivative of the formula (V) and a base are mixed in a suitable diluent; the mixture is stirred at the required temperature until the reaction has ended and then worked up in the customary manner.
  • the active ingredients are suitable for combating animal pests such as insects and single ticks, which occur in animal husbandry and animal breeding in useful, breeding, zoo, laboratory, experimental and hobby animals with favorable warm-blooded toxicity. They are effective against all or individual stages of development of the pests and against resistant and normally sensitive types of pests.
  • the fight against animal pests is intended to prevent diseases and their transmission, deaths and reduced performance (for example in the production of meat, milk, wool, hides, eggs), so that the use of the active compounds enables more economical and simple animal husbandry or is only possible in certain areas.
  • the pests include:
  • Eomenacanthus spp. Menacanthus spp., Trichodectes spp., Felicola spp.,
  • Damalinea spp. Bobiola spp., Trinoton spp., Werneckiella spp., Lepikeutron spp .; from the order of the Diptera e.g. Chrysops spp., Tabanus spp., Musca spp.,
  • Hydrotaea spp. Muscina spp., Haematobosca spp., Haematobia spp., Stomoxys spp., Fannia spp., Glossina spp., Lucilia spp., Calliphora spp., Auchmeromyia spp.,
  • Siphonaptera e.g. Ctenocephalides spp., Echidnophaga spp., Ceratophyllus spp., Pulex spp ..
  • Hyalomma spp. The following genera and species of the parasitic ticks: Hyalomma spp., Rhipicephalus evertsi, Boophilus spp., Amblyomma spp., Dermacentor spp., Ixodes ricinus, Argas spp., Ornithodorus spp., Otobius spp .; from the order of the Mesastigmata Dermanyssus spp., Pneumonyssus spp ..
  • Domestic and farm animals include mammals such as Cattle, sheep, goats, horses, pigs, dogs, cats, camels, water buffalos, donkeys, rabbits, fallow deer, reindeer, fur animals such as Mink, chinchilla, raccoon, birds such as Chickens, turkeys, pheasants, geese, ducks.
  • Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters, dogs and cats.
  • the pets include dogs and cats.
  • the application can be prophylactic as well as therapeutic.
  • the active ingredients are used directly or in the form of suitable preparations enterally, parenterally, dermally, nasally, by treating the environment or with the aid of shaped articles containing active ingredients, such as, for example, strips, plates, bands, necklaces, ear tags, limb bands, marking devices.
  • the enteral application of the active ingredients takes place, for example, orally in the form of powder, suppositories, tablets, capsules, pastes, drinkers, granules, drenches, boluses, medicated feed or drinking water.
  • the dermal application takes place, for example, in the form of dipping (dipping), spraying (spraying), bathing, washing, pouring on (pour-on and spot-on) and powdering.
  • Parenteral use is for example in the form of injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or by implants.
  • Suitable preparations are:
  • Solutions such as injection solutions, oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, infusion formulations, gels;
  • Emulsions and suspensions for oral or dermal use and for injection Semi-solid preparations
  • Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; Aerosols and inhalants, molded articles containing active ingredients.
  • Solutions for injection are administered intravenously, intramuscularly and subcutaneously.
  • Injection solutions are prepared by dissolving the active ingredient in a suitable solvent and possibly additives such as solubilizers, acids,
  • Bases can be added.
  • the solutions are sterile filtered and filled.
  • solvents physiologically compatible solvents such as water, alcohols such as ethanol, butanol, benzyl alcohol, glycerol, hydrocarbons, propylene glycol, polyethylene glycols, N-methylpyrrolidone, and mixtures thereof.
  • the active compounds can also be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
  • solubilizers solvents which promote the dissolution of the active ingredient in the main solvent or prevent its precipitation. Examples are polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.
  • Preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol.
  • Oral solutions are applied directly. Concentrates are used orally after previous dilution to the application concentration. Oral solutions and concentrates are produced as described above for the injection solutions, whereby sterile work can be dispensed with.
  • Solutions for use on the skin are dripped on, spread on, rubbed in, sprayed on, sprayed on or applied by dipping (dipping, bathing or washing). These solutions are prepared as described above for the injection solutions.
  • Thickeners are: inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.
  • Gels are applied to or spread on the skin or placed in body cavities. Gels are produced by adding enough thickening agent to solutions which have been prepared as described for the injection solutions to produce a clear mass with an ointment-like consistency.
  • the thickeners specified above are used as thickeners.
  • Pour-on formulations are poured or sprayed onto limited areas of the skin, the active ingredient either penetrating the skin and acting systemically or being distributed over the surface of the body.
  • pour-on formulations are prepared by suspending the active ingredient in suitable skin-compatible solvents or solvent mixtures or is emulsified. If necessary, other auxiliaries such as dyes, absorption-promoting substances, antioxidants, light stabilizers and adhesives are added.
  • solvents water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol and glycol monoethyl ether Acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-methylpyrrolidone, 2,2-dimethyl-4-oxy-methylene-l, 3-dioxolane.
  • aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol
  • esters such as ethyl acetate, butyl acetate
  • benzyl benzoate ether
  • Dyes are all dyes approved for use on animals, which can be dissolved or suspended.
  • Absorbing substances are e.g. DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.
  • spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.
  • Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylated hydroxytoluene, butylated hydroxyanisole, tocopherol.
  • Light stabilizers are e.g. Substances from the class of benzophenones or novantisolic acid.
  • Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural
  • Polymers such as alginates, gelatin.
  • Emulsions can be used orally, dermally or as an injection.
  • Emulsions are either water in oil or oil in water.
  • Emulsifiers and optionally other auxiliaries such as dyes, absorption-promoting substances, preservatives, antioxidants, light stabilizers, Viscosity-increasing substances, homogenized with the solvent of the other phase.
  • hydrophobic phase paraffin oils, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric acid biglyceride, triglyceride mixtures with vegetable fatty acids of chain length C 8 _ 12 or other specially selected natural fatty acids, partial - Glyceride mixtures of saturated or unsaturated, possibly also hydroxyl-containing fatty acids, mono- and diglycerides of C 8 / C ] 0 fatty acids.
  • Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, lauric acid hexyl ester, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C 16 -C 18 , isopropyl myristate, isopropyl palmitate, caprylic / capric alcohol esters of the saturated fatty acid Chain length C 12 -C 18 , isopropyl stearate, oleic acid oleyl ester, oleic acid decyl ester, ethyl oleate, lactic acid ethyl ester, waxy fatty acid esters such as artificial duck pancreas fat, dibutyl phthalate, adipic acid diisopropyl ester, the latter related ester mixtures and others
  • Fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.
  • Fatty acids such as Oleic acid and its mixtures.
  • hydrophilic phase The following can be mentioned as the hydrophilic phase:
  • Alcohols such as e.g. Propylene glycol, glycerin, sorbitol and their mixtures.
  • nonionic surfactants e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;
  • ampholytic surfactants such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin;
  • anionic surfactants such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;
  • cationic surfactants such as cetyltrimethylammonium chloride.
  • substances which increase viscosity and stabilize the emulsion such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes , colloidal silica or mixtures of the listed substances.
  • Suspensions can be used orally, dermally or as an injection. They are produced by suspending the active ingredient in a carrier liquid, if appropriate with the addition of other auxiliaries such as wetting agents, dyes, absorption-promoting substances, preservatives, antioxidants and light stabilizers.
  • the surfactants specified above may be mentioned as wetting agents (dispersants).
  • Semi-solid preparations can be administered orally or dermally. They differ from the suspensions and emulsions described above only in their higher viscosity.
  • the active ingredient is mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape.
  • Inorganic substances are e.g. Table salt, carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides, silicas, clays, precipitated or colloidal silicon dioxide, phosphates.
  • Organic substances are, for example, sugar, cellulose, food and feed such as milk powder, animal meal, cereal meal and meal, starches. Excipients are preservatives, antioxidants, dyes, which have already been listed above.
  • auxiliaries are lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decay-promoting substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinylpyrrolidone and dry binders such as microcrystalline cellulose.
  • lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decay-promoting substances such as starch or cross-linked polyvinylpyrrolidone, binders such as e.g. Starch, gelatin or linear polyvinylpyrrolidone and dry binders such as microcrystalline cellulose.
  • the active substances can also be present in the preparations as a mixture with synergists or with other active substances.
  • Ready-to-use preparations contain the active substance in concentrations of
  • Preparations which are diluted before use contain the active ingredient in concentrations of 0.5 to 90% by weight, preferably 5 to 50% by weight.
  • the active compound (1) used in the following examples is the compound of the formula:
  • SC- (suspension concentrate) formulation :
  • Marlon AT 50 a triethanolamine salt of alkylbenzenesulfonic acids from Huls AG 11.1% by weight of Marlon A 350, sodium salt of alkylbenzenesulfonic acids from Huls AG
  • the solvent is then distilled off, the residue is taken up in 100 ml of ethyl acetate and washed three times with 50 ml of water each time.
  • the solvent is stripped off and the residue is purified by chromatography on silica gel column chromatography with toluene / toluene, ethyl acetate 10: 1 as the eluent.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Engineering & Computer Science (AREA)
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  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne l'utilisation de composés de la formule (I) où B représente alkyle, alkényle, cycloalkyle, cycloalkényle, aryle éventuellement substitués; A représente aryle, aryloxy, hétéroaryle, hétéroaryloxy éventuellement substitués et éventuellement liés au composé cyclique oxazoline par un reste Z bivalent; R représente hydrogène ou bien, conjointement avec A et l'atome C adjacent, un composé spirocyclique ayant 3 à 6 chaînons, lequel comprend éventuellement un ou plusieurs hétéroatomes du groupe O, S, N et auquel est éventuellement condensé un autre composé cyclique, le système étant éventuellement substitué, pour lutter contre les insectes et les tiques monoxènes chez l'homme et les animaux.
PCT/EP1996/002284 1995-06-08 1996-05-28 Utilisation d'oxazolines pour lutter contre les ectoparasites Ceased WO1996041534A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BR9609252A BR9609252A (pt) 1995-06-08 1996-05-28 Composições ectoparasiticidas
EP96916163A EP0831704A1 (fr) 1995-06-08 1996-05-28 Utilisation d'oxazolines pour lutter contre les ectoparasites
JP9502549A JP2000501695A (ja) 1995-06-08 1996-05-28 外部寄生虫を防除するためのオキサゾリンの使用
AU59020/96A AU5902096A (en) 1995-06-08 1996-05-28 Use of oxazolines for combatting ectoparasites
SK1662-97A SK166297A3 (en) 1995-06-08 1996-05-28 Use of oxazolines for combatting ectoparasites

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19520936.2 1995-06-08
DE19520936A DE19520936A1 (de) 1995-06-08 1995-06-08 Ektoparasitizide Mittel

Publications (1)

Publication Number Publication Date
WO1996041534A1 true WO1996041534A1 (fr) 1996-12-27

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ID=7763930

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PCT/EP1996/002284 Ceased WO1996041534A1 (fr) 1995-06-08 1996-05-28 Utilisation d'oxazolines pour lutter contre les ectoparasites

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EP (1) EP0831704A1 (fr)
JP (1) JP2000501695A (fr)
KR (1) KR19990022300A (fr)
CN (1) CN1192651A (fr)
AR (1) AR003433A1 (fr)
AU (1) AU5902096A (fr)
BR (1) BR9609252A (fr)
CA (1) CA2223147A1 (fr)
CZ (1) CZ395597A3 (fr)
DE (1) DE19520936A1 (fr)
HU (1) HUP9900369A2 (fr)
PL (1) PL323861A1 (fr)
SK (1) SK166297A3 (fr)
TR (1) TR199701531T1 (fr)
WO (1) WO1996041534A1 (fr)
ZA (1) ZA964831B (fr)

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US6413912B2 (en) 1997-11-04 2002-07-02 Syngenta Crop Protection, Inc. Azoline derivatives
US8110589B2 (en) 2008-06-17 2012-02-07 Kyoyu Agri Co., Ltd. Ectoparasiticide composition and a method for exterminating extoparasites

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US6413912B2 (en) 1997-11-04 2002-07-02 Syngenta Crop Protection, Inc. Azoline derivatives
US8110589B2 (en) 2008-06-17 2012-02-07 Kyoyu Agri Co., Ltd. Ectoparasiticide composition and a method for exterminating extoparasites

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AR003433A1 (es) 1998-08-05
CA2223147A1 (fr) 1996-12-27
MX9709648A (es) 1998-07-31
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JP2000501695A (ja) 2000-02-15
CZ395597A3 (cs) 1998-05-13
HUP9900369A2 (hu) 1999-05-28
KR19990022300A (ko) 1999-03-25
AU5902096A (en) 1997-01-09
DE19520936A1 (de) 1996-12-12
EP0831704A1 (fr) 1998-04-01
BR9609252A (pt) 1999-05-11
TR199701531T1 (xx) 1998-05-21
PL323861A1 (en) 1998-04-27
CN1192651A (zh) 1998-09-09

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