WO2002049436A1 - Corps moules contenant une oxime de pyrazole pour lutter contre des parasites cutanes sur des animaux - Google Patents

Corps moules contenant une oxime de pyrazole pour lutter contre des parasites cutanes sur des animaux Download PDF

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Publication number
WO2002049436A1
WO2002049436A1 PCT/EP2001/014452 EP0114452W WO0249436A1 WO 2002049436 A1 WO2002049436 A1 WO 2002049436A1 EP 0114452 W EP0114452 W EP 0114452W WO 0249436 A1 WO0249436 A1 WO 0249436A1
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alkyl
halogen
hydrogen
substituted
spp
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PCT/EP2001/014452
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German (de)
English (en)
Inventor
Kirkor Sirinyan
Olaf Hansen
Andreas Turberg
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Bayer Aktiengesellschaft
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Priority to AU2002221946A priority Critical patent/AU2002221946A1/en
Publication of WO2002049436A1 publication Critical patent/WO2002049436A1/fr

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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to pyrazoloxime-containing moldings for dermal
  • solid formulation New, user-friendly and environmentally friendly moldings, called solid formulation in the application, have now been rounded off for the dermal use of pyrazole oximes which are particularly suitable for the dermal control of parasitic arthropods on animals. These solid formulations are particularly effective against the ectoparasites, normally sensitive and resistant species, and against all or some stages of development of the animals mentioned.
  • the invention therefore relates to solid formulations for the dermal control of
  • the invention further relates to the use of the solid formulations according to the invention for the dermal control of parasites on animals.
  • Suitable pyrazole oximes with insecticidal and acaricidal activity are described, for example, in EP-A-0234 045, to which reference is expressly made.
  • R 1 is C r C 4 alkyl or phenyl
  • R 2 is hydrogen, C j -Cs alkyl, or phenyl means
  • R 3 is hydrogen, -CC 4 -alkyl or phenyl
  • R 4 is hydrogen, C 2 -C 4 alkylcarbonyl. Benzoyl, naphthyl or a substituent of the formula
  • X represents hydrogen, halogen
  • R 6 is hydrogen, alkali metal, Cj-CiQ-alkyl, -C-C 5 alkyl substituted with halogen, -CC 4 alkoxy, phenoxy, C 2 -C 4 alkoxycarbonyl or phenoxyphenyl; C 2 -C 7 alkenyl; C 3 -C 7 alkynyl; C 3 -C 8 cycloalkyl; C 3 -C 8 cycloalkyl substituted with C r C 3 alkyl; phenyl; -S n R7R8R9 (which in R 7 , R 8 and R9 are the same or different and or C -Cg-cycloalkyl)) ⁇ ; C 2 -C 6 alkylcarbonyl; C 2 -C 6 alkylcarbonyl substituted with cyano or C 2 -Cg alkoxycarbonyl; Benzoyl optionally substituted with
  • R 14 is hydrogen, C 1 -C alkyl or C 2 -C 6 alkoxyalkyl
  • -C (BR 15 ) (BR 16 ) (R 17 ) in which R 15 and R 16 may be the same or different and stand for C 1 -C 4 -alkyl or together form a C 1 -C 4 alkylene radical, R 17 for Ci -Cs-alkyl, cyano or C2-C6-alkoxycarbonyl and B is oxygen or sulfur
  • -C (OR 18 ) R 1 R 20 in which R 18 is hydrogen or C 2 -C 4 -alkylcarbonyl and R 19 and R 20 are identical or different and are hydrogen or C r C 6 alkyl
  • -SiR 21 R 22 R 23 in which R 21 ,
  • R 22 and R 23 are the same or different and are C 1 -C 4 alkyl); or -O-SiR 24 R 25 R 26 (in which R 24 , R 25 and R 26 are identical or different and represent C 1 -C 4 -alkyl), and
  • n is an integer from 1 to 5, where when n is an integer from 2 to 5, X can be the same or different];
  • Y is hydrogen, C ⁇ -C-alkyl, -C-C -haloalkyl, halogen, hydroxy, C1-C4- haloalkoxy, -C-C 3 -alkylenedioxy, phenoxy, which is optionally substituted with trifluoromethyl, -S (O) q R 27 (in which R 27 is C r C 3 -alkyl and q is 0, 1 or 2), hydroxycarbonyl, C 2 -C 5 -alkoxycarbonyl or -NR 8 R 29 (in which R 28 and R 29 are identical or different and are for Is hydrogen, -CC-alkyl or benzyl, which is optionally substituted with C 2 -C 6 -alkoxycarbonyl);
  • Z * represents oxygen or sulfur
  • Z 2 represents oxygen, sulfur or a single bond
  • Z 3 represents aryl or heteroaryl
  • Q is Ci-Cg-alkylene, Cj-Cg-alkylene substituted with halogen or phenyl, C 3 -C ⁇ 2 alkenylene, C 3 -Ci2-haloalkenylene or C 3 -C6 alkynylene;
  • n represents an integer from 1 to 3, where if m represents an integer 2 or 3, Y can be the same or different.
  • the said compounds can exist in stereoisomeric forms which either behave like image and mirror image (enantiomers) or do not behave like image and mirror image (diastereomers).
  • the invention relates both to the enantiomers or diastereomers and to their respective mixtures. Like the diastereomers, the racemic forms can be separated into the stereoisomerically uniform constituents in a known manner.
  • the compounds according to the invention can optionally be present both as ice and as trans isomers. Even if only one of the isomers is shown, the ice and trans isomers are always meant according to the invention.
  • alkyl stands for a straight-chain or branched alkyl, alkenyl or alkynyl radical having 1 to 12 carbon atoms.
  • a straight-chain or branched alkyl, alkenyl or alkynyl radical is preferred with 1 to 6, particularly preferably 1 to 4 carbon atoms.
  • alkyl radicals are: methyl, ethyl, n-propyl, isopropyl, t-butyl, n-pentyl and n-hexyl.
  • alkenyl radicals are: vinyl, Allyl, isopropenyl and n- But-2-en-l-yl.
  • alkynyl radicals are: ethynyl, n-prop-2-yn-l-yl and n-but-2-yn-l-yl.
  • haloalkyl stands for an alkyl radical as defined above in which one or more, preferably one, two or three, hydrogen atoms pass through
  • Halogen atoms (same or different) are replaced.
  • Halogen in the context of the invention stands for fluorine, chlorine, bromine and iodine.
  • aryl stands for an aromatic radical having 6 to 14, preferably 6 to 10, carbon atoms. Examples are phenyl and naphthyl, phenyl is particularly preferred.
  • heteroaryl stands for 5- to 10-membered, preferably 5- and 6-membered, aromatic rings containing heteroatoms with up to 4 heteroatoms selected from O, S and N and includes, for example: pyridyl, Furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolicenyl, indolyl, benzo [b] thienyl, benzo [b] furyl, indazolyl, quinolyl, isoquinolyl, naphthyridinyl, quinazolinyl, etc. Particularly preferred is pyridyl ,
  • substituted radicals carry one or more, preferably one, two or three identical or different substituents.
  • Particularly preferred pyrazole oximes are the compounds of the general formula (Ia) wherein
  • R 30 represents straight-chain or branched alkyl having up to 6 carbon atoms and
  • R 31 represents aryl or heteroaryl, which can each be substituted by halogen.
  • the solid formulations according to the invention should advantageously release amounts of active ingredient from 10 to about 300 mg, preferably 20 to 200 mg, particularly preferably 25 to 160 mg per kg of body weight of the animal to be treated in the course of at least three months in order to counteract a good activity To be able to guarantee fleas and ticks.
  • the solid formulations according to the invention are preferably
  • Shaped bodies include collars, pendants for collars (medallions), ear tags, ribbons for attachment to limbs or body parts, adhesive strips and foils, peel-off foils. Collars and medallions deserve special mention.
  • Thermoplastic and flexible or thermosetting plastics as well as elastomers and thermoplastic elastomers are suitable for the production of the shaped bodies.
  • Polyvinyl resins, polyurethanes, polyacrylates, epoxy resins, cellulose, cellulose derivatives, polyamides and polyesters which are sufficiently compatible with the abovementioned active ingredient may be mentioned as such.
  • the polymers must have sufficient strength and flexibility so that they do not crack or become brittle during molding. They must be of sufficient durability to withstand normal wear and tear. In addition, the polymers must allow the active ingredient to migrate sufficiently to the surface of the molding.
  • the polyvinyl resins include polyvinyl halides, such as polyvinyl chloride, polyvinyl chloride vinyl acetate and polyvinyl fluoride; Polyacrylate and polymethacrylate esters, such as polymethyl acrylate and polymethyl methacrylate; and polyvinylbenzenes, such as
  • Polystyrene and polyvinyltoluene Special mention should be made of polyvinyl chloride.
  • plasticizers which are usually used to plasticize solid vinyl resins are suitable for the production of the molded articles based on polyvinyl resin.
  • the plasticizer to be used depends on the resin and its compatibility with the plasticizer.
  • Suitable plasticizers are, for example, esters of phosphoric acid, such as esters of phthalic acid, such as dimethyl phthalate and di-octyl phthalate, and esters of adipic acid, such as diisobutyl adipate.
  • esters such as the esters of azelaic acid, maleic acid, ricinoleic acid, myristic acid, palmitic acid, oleic acid, sebacic acid, stearic acid and trimellitic acid, as well as complex linear polyesters, polymeric plasticizers and epoxidized soybean oils can also be used.
  • the amount of plasticizer is about 10 to 50%, preferably about 20 to 45% by weight of the total composition.
  • Lubricants, mold release agents, fillers and coloring materials can be included without that this changes the basic properties of the composition.
  • Suitable stabilizers are antioxidants and agents that protect the tapes from ultraviolet radiation and unwanted degradation during processing, such as extrusion.
  • stearates, stearic acid and low molecular weight polyethylenes can be used as lubricants. These ingredients can be used in a concentration up to about 5% by weight of the total composition.
  • the various constituents are mixed by known processes and compression-molded by known extrusion or injection molding processes.
  • the choice of the processing method for the production of the shaped body is basically based on the theological properties of the strip material and the shape of the desired strip.
  • the processing methods can be set according to the processing technology or the type of shaping. In process technology, the processes can be subdivided according to the theological states they run through. Then come for viscous tape materials
  • the shaped bodies according to the invention can be produced by casting, dipping, pressing, injection molding, extruding, calendering, embossing, bending, deep-drawing, etc.
  • polyvinyl resins are known and require no further explanation. In principle, the explanations given above for polyvinyl resins apply to other polymers.
  • the polyurethanes used as the carrier material are produced in a manner known per se by reacting polyisocyanates with higher molecular weight compounds having at least two groups which are reactive toward isocyanates, and optionally with low molecular weight chain extenders and / or monofunctional chain terminators.
  • Suitable starting components in the production of the polyurethanes are aliphatic, cycloaliphatic, araliphatic, aromatic and heterocyclic polyisocyanates, such as those e.g. by W. Siefken in Liebig's Annalen der Chemie, 562, pages 75 to 136. Examples include: ethylene diisocyanate, 1,4-
  • distillation residues obtained in industrial isocyanate production and containing isocyanate groups optionally dissolved in one or more of the aforementioned polyisocyanates. It is also possible to use any mixtures of the aforementioned polyisocyanates.
  • Preferred polyisocyanates are generally the tolylene diisocyanates and the diphenylmethane diisocyanates.
  • Starting components for the production of the polyurethanes are furthermore compounds having at least two isocyanate-reactive hydrogen atoms with a molecular weight of generally 400-10,000.
  • these are preferably polyhydroxyl compounds, in particular two to eight compounds containing hydroxyl groups, especially those with a molecular weight of 800 to 10,000, preferably 1,000 to 6,000, for example at least two, usually 2-8, but preferably 2-4, hydroxyl-containing polyesters, polyethers, polythioethers, polyacetals, polycarbonates and polyesteramides, as described for the production of homogeneous and cellular polyurethanes are known per se.
  • the hydroxyl group-containing polyesters are, for example, reaction products of polybasic, preferably dibasic and optionally additionally trihydric, carboxylic acids.
  • the corresponding polycarboxylic acid anhydrides or corresponding polycarboxylic acid esters of lower alcohols or mixtures thereof can also be used to prepare the polyesters.
  • the polycarboxylic acids can be more aliphatic. be cycloaliphatic, aromatic and / or heterocyclic in nature and optionally substituted, for example by halogen atoms, and / or unsaturated.
  • Examples include: succinic acid, adipic acid, suberic acid,
  • Dimethyl terephthalate and bis-glycol terephthalate Dimethyl terephthalate and bis-glycol terephthalate.
  • polyhydric alcohols are e.g. Ethylene glycol, propylene glycol (1,2) and - (1,3), butylene glycol (1,4) and - (2,3), hexanediol .- (1,6), octanediol- (1,8), neopentygly col, cyclohexanedimethanol (1,4-bis-hydroxy-methylcyclohexane), 2-methyl-1,3-propanediol, glycerol, trimethylolpropane, hexanetriol- (1,2,6), butanetriol- (1,2,4), Trimethylethane, pentaerythritol, quinite, mannitol and sorbitol, methyl glycol, furthermore diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycols, dipropylene glycol, polypropylene glycols, dibutylene glycol and polybutylene glyco
  • Lactones e.g. ⁇ -caprolactone or hydroxycarboxylic acids, e.g. ⁇ -hydroxycaproic acid can be used.
  • polyethers which have at least two, generally two to eight, preferably two to three, hydroxyl groups. These are known per se and are, for example, by polymerization of epoxides such as Ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin with itself, for example in the presence of BF 3 or by addition of these epoxides, optionally in a mixture or in succession, to starting components with reactive hydrogen atoms such as water, alcohols, ammonia or amines , e.g. ethylene glycol, propylene glycol- (1,3) or - (1,2), trimethylolpropane, 4,4'-
  • epoxides such as Ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin
  • reactive hydrogen atoms such as water, alcohols, ammonia or amine
  • sucrose polyethers e.g. described in DE-ASen 1 176 358 and 1 064 938 come into question. In many cases, those polyethers are preferred which predominantly (up to 90% by weight, based on all the OH groups present in the polyether) have primary OH groups.
  • Polyethers modified by vinyl polymers such as those e.g. by polymerization of styrene and acrylonitrile in the presence of polyethers (US Pat. Nos. 3,383,351, 3,304,273, 3,523,093, 3,110,695, German Patent 1,152,536) are suitable, as are OH-containing polybutadienes.
  • the condensation products on thiodiglycol with themselves and / or with other glycols, dicarboxylic acids, formaldehyde, aminocarboxylic acids or amino alcohols should be mentioned in particular.
  • the products are polythio mixed ethers, polythioether esters or polythioether ester amides.
  • polyacetals e.g. the compounds which can be prepared from glycols, such as diethylene glycol, triethylene glycol, 4,4'-dioxethoxydiphenyldimethylmethane, hexanediol and formaldehyde.
  • glycols such as diethylene glycol, triethylene glycol, 4,4'-dioxethoxydiphenyldimethylmethane, hexanediol and formaldehyde.
  • Polyacetals suitable according to the invention can also be prepared by polymerizing cyclic acetals.
  • Suitable polycarbonates containing hydroxyl groups are those of the type known per se, for example those obtained by reacting diols such as propanediol (1,3), butanediol (1,4) and / or hexanediol (1,6), diethylene glycol, triethylene glycol or tetraethylene glycol with diaryl carbonates, for example diphenyl carbonate, or phosgene can be produced.
  • the polyester amides and polyamides include, for example, the predominantly linear condensates obtained from polyvalent saturated and unsaturated carboxylic acids or their anhydrides and polyvalent saturated and unsaturated amino alcohols, diamines, polyamines and their mixtures.
  • Polyhydroxyl compounds already containing urethane or urea groups and optionally modified natural polyols, such as castor oil, carbohydrates or starch, can also be used.
  • Addition products of alkylene oxides on phenol-formaldehyde resins or also on urea-formaldehyde resins can also be used according to the invention.
  • Compounds with at least two isocyanate-reactive hydrogen atoms with a molecular weight of 32-400 can also be used as starting components which may be used.
  • These compounds generally have 2 to 8 isocyanate-reactive hydrogen atoms, preferably 2 or 3 reactive hydrogen atoms. Examples of such connections are:
  • mixtures of different compounds with at least two isocyanate-reactive hydrogen atoms with a molecular weight of 32-400 can be used.
  • polyhydroxyl compounds can also be used, in which high molecular weight polyadducts or polycondensates are contained in finely dispersed or dissolved form.
  • modified polyhydroxyl compounds are obtained if polyaddition reactions (for example reactions between polyisocyanates and ammofunctional compounds) or polycondensation reactions (for example between formaldehyde and phenols and / or amines) are carried out directly in situ in the above-mentioned compounds containing hydroxyl groups.
  • the finished polyurethane should not be swellable in water.
  • the use of an excess of polyhydroxyl compounds with ethylene oxide units should therefore be avoided.
  • Thermoplastic materials are particularly emphasized for the production of the shaped bodies
  • Elastomers These are materials that contain elastomeric phases in thermoplastically processable polymers either physically mixed in or chemically bound. A distinction is made between polymer blends in which the elastomeric phases are part of the polymer structure. Due to the structure of the thermoplastic elastomers, hard and soft areas are side by side.
  • the hard areas form a crystalline network structure or a continuous phase whose spaces are filled with elastomeric segments. Because of this structure, these materials have rubber-like properties.
  • thermoplastic elastomers There are 5 main groups of thermoplastic elastomers:
  • PEBA polyether block amides
  • TPU thermoplastic polyurethanes
  • TPO thermoplastic polyolefins
  • Suitable copolyesters are composed, for example, of a large number of recurring, short-chain ester units and long-chain ester units which are combined by ester bonds, the short-chain ones Ester units make up about 15-65% by weight of the copolyester and have the formula (Q).
  • R represents a divalent radical of a dicarboxylic acid which has a molecular weight of less than about 350
  • D represents a divalent radical of an organic diol that has a molecular weight below about 250.
  • the long chain ester units make up about 35-85% by weight of the copolyester and have the formula (m)
  • R represents a divalent radical of a dicarboxylic acid which has a molecular weight of less than about 350
  • copolyesters which can be used according to the invention can be prepared by polymerizing together a) one or more dicarboxylic acids, b) one or more linear, long-chain glycols and c) one or more low molecular weight diols.
  • the dicarboxylic acids for the preparation of the copolyester can be aromatic, aliphatic or cycloaliphatic.
  • the preferred dicarboxylic acids are the aromatic acids with 8-16 carbon atoms, especially phenylenedicarboxylic acids, such as phthalic, terephthalic and isophthalic acid.
  • the low molecular weight diols for the reaction to form the short-chain ester units of the copolyesters belong to the classes of the acyclic, alicyclic and aromatic dihydroxy compounds.
  • the preferred diols have 2-15 carbon atoms, such as ethylene, propylene, tetramethylene, isobutylene, pentamethylene, 2,2-dimethyltrimethylene, hexamethylene and decamethylene glycols, dihydroxycyclohexane, cyclohexanedimethanol, resorcinol, hydroquinone and the like
  • Bisphenols for the present purpose include bis (p-hydroxy) diphenyl, bis (p-hydroxyphenyl) methane, bis (p-hydroxyphenyl) ethane and bis (p-hydroxyphenyl) propane.
  • the long chain glycols used to make the soft segments of the copolyesters preferably have molecular weights from about 600 to 3000. They include poly
  • alkylene ether glycols in which the alkylene groups have 2-9 carbon atoms.
  • Glycol esters of poly (alkylene oxide) dicarboxylic acids can also be used as long-chain glycol.
  • Polyester glycols can also be used as long-chain glycol.
  • Long-chain glycols also include polyformals, which are produced by the implementation of
  • Formaldehyde can be obtained with glycols.
  • Polythioether glycols are also suitable.
  • Polybutadiene and polyisoprene glycols, copolymers thereof and saturated Hydrogenation products of these materials are satisfactory long chain polymeric glycols.
  • Suitable copolyesters are available, for example, under the trade names ® Hytrel from Du Pont, ® Pelpren from Toyobo ® , Arnitel from Akzo, ® Ectel from Eastman Kodak and ® Riteflex from Hoechst.
  • Suitable polyether block amides are, for example, those which consist of polymer chains which are composed of repeating units corresponding to the formula (IN).
  • A is the polyamide chain derived from a polyamide with 2 carboxyl end groups by loss of the latter and
  • B is the polyoxyalkylene glycol with terminal OH groups derived from loss of the latter polyoxyalkylene glycol chain and
  • n is the number of units forming the polymer chain.
  • the end groups here are preferably OH groups or residues of compounds which terminate the polymerization.
  • the dicarboxylic acid polyamides with the terminal carboxyl groups are obtained in a known manner, for example by polycondensation of one or more lactams or / and one or more amino acids, furthermore by polycondensation of a dicarboxylic acid with a diamine, in each case in the presence of an excess of an organic dicarboxylic acid, preferably with terminal carboxyl groups , These carboxylic acids become part of the polyamide chain during the polycondensation and attach themselves in particular to the end of the chain, thereby obtaining a polyamide which is ° C- ⁇ -dicarboxylic acid. Furthermore, the dicarboxylic acid acts as a chain terminator, which is why it is also used in excess.
  • the polyamide can be obtained starting from lactams and / or amino acids with a hydrocarbon chain consisting of 4-14 C atoms, e.g. of caprolactam, oenantholactam, dodecalactam, undekanolactam, decanolactam, 11-amino-undecanoic or 12-aminododecanoic acid.
  • polyamides such as those formed by polycondensation of a dicarboxylic acid with a diamine
  • condensation products of hexamethylenediamine with adipic, azelaic, sebacic and 1,12-dodecanedioic acid are the condensation products of nonamethylene diamine and adipic acid.
  • those with 4-20 C atoms are suitable, in particular alkanedioic acids, such as amber, adipic, cork -, Azelaic, sebacic, undecanedioic or dodecanedioic acid, furthermore cycloaliphatic or aromatic dicarboxylic acid, such as terephthalic or isphthalic or cyclohexane-l, 4-dicarboxylic acid.
  • the polyoxyalkylene glycols containing terminal OH groups are unbranched or branched and have an alkylene radical with at least 2 carbon atoms.
  • these are polyoxyethylene, polyoxypropylene and polyoxytetramethylene glycol, as well as copolymers thereof.
  • the average molecular weight of these OH-Grappen-terminated polyoxyalkylene glycols can be in a wide range, advantageously between 100 and 6000, in particular between 200 and 3000.
  • the proportion by weight of the polyoxyalkylene glycol, based on the total weight of the polyoxyalkylene glycol and dicarboxylic acid polyamide used to produce the PEBA polymer, is 5-85%, preferably 10-50%.
  • PEBA polymers which, in contrast to those previously described, have a statistical structure are particularly suitable. A is used to produce these polymers
  • polyamide-forming compounds from the group of ⁇ -aminocarboxylic acids or lactams with at least 10 carbon atoms
  • PEBA polymers are e.g. in DE-OS 2 712 987.
  • PEBA polymers are available, for example, under the trade names ® PEBAX from Atoche, ® Vestamid from Hüls AG, ® Grilamid from EMS-Chemie and ® Kellaflex from DSM.
  • the solid formulations according to the invention are suitable for combating parasites which occur in animal husbandry and animal breeding in domestic and farm animals, as well as zoo, laboratory, experimental and hobby animals, with favorable warm-blood toxicity. They are effective against normally sensitive and resistant species and against all or individual stages of development of the animals mentioned.
  • Parasites are particularly arthropods, preferably insects and arachnids.
  • the solid formulations according to the invention are preferably used to control ectoparasites.
  • ectoparasites include: tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • tick ticks include: tick ticks, leather ticks, mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings and fleas.
  • Nematocerina and Brachycerina for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.
  • Atylotus spp. Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
  • Amblyomma spp. Boophilus spp., Dermacentor spp., Haemophysahs spp., Hyalomma spp., Rhipicephafus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp ..
  • Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
  • the livestock and breeding animals include mammals such as cattle, horses, sheep, pigs, goats, camels, water buffalo, donkeys, rabbits, fallow deer, reindeer; Fur animals such as B. mink, chinchilla, raccoon; such as chickens, geese, turkeys, ducks.
  • Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters, dogs and cats.
  • the pets include dogs and cats.
  • the agents according to the invention are particularly suitable for the treatment of cattle, dogs and cats, preferably for controlling ticks and / or fleas.
  • the application can be prophylactic as well as therapeutic.
  • the moldings contain active compound in concentrations of 1 to 30% by weight, preferably 5 to 20% by weight, particularly preferably 7.5 to 12.5% by weight, based on the total mass of the solid formulation.
  • the concentration of the active substances is preferably 1 to 15%; in the case of medallions, pendants and ear tags preferably 5 to 20%, in the case of foils, adhesive strips preferably 0.1 to 5%.
  • the new solid formulations can also contain other active ingredients, such as
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • co-active substances are, for example, the following: Insecticides / acaricides / nematicides:
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron,
  • Chlormephos Chlorpyrifos, Chlorpyrifos M, Chlovaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermazine, Cypermethrin
  • Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim
  • Fenoxycarb fenpropathrin, fenpyrad, fenpyrithrin, fenvalerate, fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, Flufenoxuron, Flumethrin, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Metolcarb Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos, Moxidectin,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifene,
  • oxalate hydrogen Taufluvalinate, tebufenozide, tebufenpyrad, Tebupirimiphos, teflubenzuron, tefluthrin, temephos, Temivinphos, terbufos, tetrachlorvinphos, Thetacypermethrin, thiamethoxam, Thiapronil, Thiatriphos, thiocyclam, thiodicarb, thiofanox, thuringiensin, Tralocythrin, tralomethrin, triarathene, Triazamate, triazophos, triazuron, Trichlophenidines, trichlorfon, triflumuron, trimethacarb,
  • Diethofencarb difenoconazole, dimethirimol, dimethomorph, diniconazole, Diniconazol-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxolon,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, Tolclofosmethyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
  • N-formyl-N-hydroxy-DL-alanine sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
  • Urea in particular benzoylureas and synergists such as PBO (piperenyl butoxide) may be mentioned as further co-active ingredients.
  • PBO piperenyl butoxide
  • Benzoylureas include compounds of the formula (V):
  • R 1 represents halogen
  • R 2 represents hydrogen or halogen
  • R 3 represents hydrogen, halogen or C.-4-al yl
  • R 4 for halogen, 1-5-halogeno-C-alkyl, C -alkoxy, l-5-halo-C ⁇ - 4 -alkoxy, C -alkylthio, 1-5-halo-C -alkylthio, phenoxy or pyridyloxy which, if appropriate can be substituted by halogen, C - alkyl, 1-5- Halogen-d- 4 -alkyl, C- 4 -alkoxy, 1-5-halogen-C M -alkoxy, C ⁇ - 4 -alkylthio, 1-5-halo-d -C -alkylthio.
  • the solid formulations according to the invention which can be applied dermally, are outstandingly suitable for carrying out dermal treatments on dogs and cats.
  • Composition Fenpyroximate 10.00 g
  • Epoxidized soybean oil 2.30 g
  • Composition Fenpyroximate 10.00 g
  • Epoxidized soybean oil 2.30 g
  • Composition Fenpyroximate 20.00 g
  • Epoxidized soybean oil 2.30 g
  • Composition Fenpyroximate 10.00 g
  • Epoxidized soybean oil 2.30 g
  • the mixture of triacetin and epoxidiei is applied in a mixer to the homogeneous mixture of PVC and imidacloprid. Heating promotes, e.g. due to an increase in the number of revolutions of the mixer, the drawing of the plasticizer into the PVC. After the stearic acid has been homogeneously mixed in, the mixture is extruded in an extruder to form plates from which medallions ( ⁇ pendants for collars) are punched out.
  • Composition Fenpyroximate 5.00 g
  • Polyether block amide (Pebax ® ) 84.50 g
  • Composition Fenpyroximate 10.00 g
  • Polyether block amide (Pebax ® ) 64.50 g
  • Medium-chain triglycerides are applied in a mixer to the homogeneous mixture of imidacloprid and polyether block amide. Heating promotes the pulling in of the medium-chain triglycerides into the polyether block amide.
  • Composition Fenpyroximate 10.00 g styrene-butylene block copolymer
  • Composition Fenpyroximate 5.00 g
  • Copolyester (Hytrel ® ) 90.00 g diphenyl urea 5.00 g
  • Composition Fenpyroximate 10.00 g
  • Example A Efficacy against fleas (Ctenocephalides felis) in dogs
  • the animals are treated.
  • the dogs in the control group are not treated.
  • the medicinal products to be tested are administered to the animals as collars or medallions. Collars and medallions remain on the animal until the end of the experiment on day 170. Only 1 collar or 1 medallion is applied to each animal. Only clinically healthy animals are used.
  • Example B Efficacy against ticks (Ixodes ricinus) in dogs
  • the animals are treated.
  • the dogs in the control group are not treated.
  • the medicinal products to be tested are administered to the animals as collars or medallions. Collars and medallions remain on the animal until the end of the experiment on day 170. Only 1 collar or 1 medallion is applied to each animal. Only clinically healthy animals are used.
  • Ixodes ricinus ($ 25, $ 25) reinfested per dog.
  • One and two days after reinfestation all dogs are checked for live and dead sucked ticks. The results are logged in the raw data. On the second day after reinfestation, all living and dead ticks are removed from the dog.
  • a modified Abbott formula is used to calculate the effectiveness:
  • Effectiveness% ZIZ-Z ---- ZZZ - Z ---- ZZ X 100

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des corps moulés contenant une oxime de pyrazole pour lutter contre des parasites cutanés sur des animaux. Ces corps moulés comprennent des colliers, des médaillons pour colliers, des marques auriculaires, des rubans à fixer sur des membres ou des parties du corps, des rubans et des films adhésifs, des films pelables. On utilise de préférence des oximes de pyrazole de formule générale (I), notamment du fenpyroximate.
PCT/EP2001/014452 2000-12-21 2001-12-10 Corps moules contenant une oxime de pyrazole pour lutter contre des parasites cutanes sur des animaux WO2002049436A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002221946A AU2002221946A1 (en) 2000-12-21 2001-12-10 Moulded bodies containing pyrazole oxime for controlling skin parasites on animals

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2000163864 DE10063864A1 (de) 2000-12-21 2000-12-21 Pyrazoloximhaltige Formkörper zur dermalen Bekämpfung von Parasiten an Tieren
DE10063864.3 2000-12-21

Publications (1)

Publication Number Publication Date
WO2002049436A1 true WO2002049436A1 (fr) 2002-06-27

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Country Status (3)

Country Link
AU (1) AU2002221946A1 (fr)
DE (1) DE10063864A1 (fr)
WO (1) WO2002049436A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006000335A1 (fr) * 2004-06-29 2006-01-05 Bayer Healthcare Ag Corps façonnes solides contenant des principes actifs, a usage externe, servant a lutter contre les parasites chez les animaux
AU2005251570B2 (en) * 2004-05-12 2011-03-31 Nano Cutting Edge Technologies Pvt. Ltd. Anti-microbial activity of biologically stabilized silver nano particles
EP2347653A3 (fr) * 2009-12-28 2014-02-26 Sumitomo Chemical Company, Limited Composition pour la lutte contre les ectoparasites d'animaux

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0234045A2 (fr) * 1985-12-27 1987-09-02 Nihon Nohyaku Co., Ltd. Dérivé de pyrazole oxime et procédé de préparation et application
EP0341048A1 (fr) * 1988-05-06 1989-11-08 Sumitomo Chemical Company, Limited Composé de pyrazole sa préparation et son utilisation
EP0361827A1 (fr) * 1988-09-29 1990-04-04 Sumitomo Chemical Company, Limited Composés de pyrazole, procédé de leur préparation, leur utilisation et intermédiaires pour leur fabrication
EP0390498A1 (fr) * 1989-03-31 1990-10-03 Sumitomo Chemical Company, Limited Composé hétérocyclique, sa préparation et son utilisation
EP0391685A1 (fr) * 1989-04-07 1990-10-10 Ube Industries, Ltd. Dérivés de pyrazole oxime et insecticides, acaricides et fongicides
DE4200742A1 (de) * 1991-01-17 1992-07-23 Ciba Geigy Ag Iminomethylpyrazole
FR2746585A1 (fr) * 1996-03-29 1997-10-03 Rhone Merieux Collier anti-puces et anti-tiques pour chien et chat, a base de n-phenylpyrazole

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0234045A2 (fr) * 1985-12-27 1987-09-02 Nihon Nohyaku Co., Ltd. Dérivé de pyrazole oxime et procédé de préparation et application
EP0341048A1 (fr) * 1988-05-06 1989-11-08 Sumitomo Chemical Company, Limited Composé de pyrazole sa préparation et son utilisation
EP0361827A1 (fr) * 1988-09-29 1990-04-04 Sumitomo Chemical Company, Limited Composés de pyrazole, procédé de leur préparation, leur utilisation et intermédiaires pour leur fabrication
EP0390498A1 (fr) * 1989-03-31 1990-10-03 Sumitomo Chemical Company, Limited Composé hétérocyclique, sa préparation et son utilisation
EP0391685A1 (fr) * 1989-04-07 1990-10-10 Ube Industries, Ltd. Dérivés de pyrazole oxime et insecticides, acaricides et fongicides
DE4200742A1 (de) * 1991-01-17 1992-07-23 Ciba Geigy Ag Iminomethylpyrazole
FR2746585A1 (fr) * 1996-03-29 1997-10-03 Rhone Merieux Collier anti-puces et anti-tiques pour chien et chat, a base de n-phenylpyrazole

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2005251570B2 (en) * 2004-05-12 2011-03-31 Nano Cutting Edge Technologies Pvt. Ltd. Anti-microbial activity of biologically stabilized silver nano particles
WO2006000335A1 (fr) * 2004-06-29 2006-01-05 Bayer Healthcare Ag Corps façonnes solides contenant des principes actifs, a usage externe, servant a lutter contre les parasites chez les animaux
US7910122B2 (en) 2004-06-29 2011-03-22 Bayer Animal Health Gmbh Active compound-containing solid moulded bodies for external use against parasites on animals
AU2005256406B2 (en) * 2004-06-29 2012-01-19 Elanco Animal Health Gmbh Active substance-containing solid shaped bodies for external use against parasites in animals
EP2347653A3 (fr) * 2009-12-28 2014-02-26 Sumitomo Chemical Company, Limited Composition pour la lutte contre les ectoparasites d'animaux

Also Published As

Publication number Publication date
DE10063864A1 (de) 2002-06-27
AU2002221946A1 (en) 2002-07-01

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