WO2004064522A1 - Repellentmittel - Google Patents
Repellentmittel Download PDFInfo
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- WO2004064522A1 WO2004064522A1 PCT/EP2004/000017 EP2004000017W WO2004064522A1 WO 2004064522 A1 WO2004064522 A1 WO 2004064522A1 EP 2004000017 W EP2004000017 W EP 2004000017W WO 2004064522 A1 WO2004064522 A1 WO 2004064522A1
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- WO
- WIPO (PCT)
- Prior art keywords
- spp
- ticks
- methylpyrrolidone
- citric acid
- bht
- Prior art date
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- 0 CC(C1[C@@]2CC(O[C@@](C)CCC[C@@]([C@]3C)O*)=O)C(*)(*)C(C(*)[C@](C4)O*)[C@@]4C1C=C2C3=O Chemical compound CC(C1[C@@]2CC(O[C@@](C)CCC[C@@]([C@]3C)O*)=O)C(*)(*)C(C(*)[C@](C4)O*)[C@@]4C1C=C2C3=O 0.000 description 1
- OIRKLDAZVOZHMK-AJBSGBCOSA-N CCO[C@@H]([C@H](C)O[C@@H](C)[C@@H]1OC)[C@@H]1OC Chemical compound CCO[C@@H]([C@H](C)O[C@@H](C)[C@@H]1OC)[C@@H]1OC OIRKLDAZVOZHMK-AJBSGBCOSA-N 0.000 description 1
Classifications
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- 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
- A61P33/10—Anthelmintics
-
- 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 an arthropod repelling component of the class of pyrethroids / pyretrirines in combination with an agonist of nicotinic acetylcholine receptors of arthropods for the efficient and long-lasting repellency of arthropods, preferably on animals.
- topical formulations comprising permethrin, (3-phenoxyphenyl) methyl 3- (2,2-dichloroethenyl) -2,2-dimethylcyclopropanecarboxylate, (CAS No [52645-53-1] for controlling parasitic insects on animals is known ( See, for example, WO 95/17090, JP 07 247 203, EP-A-567 368, EP-A-461 962, US-5 236 954 and US-5 074 252).
- Agonists of the mcotinergen acetylcholine receptors of insects are known, e.g. from European Patent Laid-Open Nos. 464,830, 428,941, 425,978, 386,565, 383,091, 375,907, 364,844, 315,826, 259,738, 254,859, 235,725, 212,600, 192,060, 163,855, 154,178 , 136 636, 303 570, 302 833, 306 696, 189 972, 455 000, 135 956, 471 372, 3Q2 389; German Offenlegungsschriften Nos. 3,639,877, 3,712,307; Japanese Patent Laid-Open Nos. 03 220 176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03 279 359, 03 255 072; US Pat.
- Spot-on formulations based on agonists or antagonists of nicotinic acetylcholine receptors generally have very good activity against insects. However, they have the disadvantage that they are practically ineffective against ticks and show no repelling effect.
- WO 02/087338 describes the provision of a skin-friendly and environmentally compatible, user-friendly formulation effective against parasitic insects, in particular against ticks and fleas, for dermal application containing permethrin and agonists or antagonists of the nicotinergic acetylcholine receptors of insects.
- agents containing pyrethroids / pyrethrins group in combination with agents which act agonistically on the arthropod nicotine receptor have very good repelling properties against arthropods, e.g. Ticks, mosquitoes and flies beyond the repellent effect of formulations containing pyrethroid / pyrethrin alone.
- a method of repellating arthropods of warm-blooded animals wherein a pyrethroid or pyrethrin in combination with a nicotinic agonist applied topically to the warm-blooded animals.
- a method for locating arthropods of sites and materials in which they are undesirable comprising applying a pyrethroid or pyrethrin in combination with a nicotinic agonist to the locus or material from which the arthropods are to be kept away.
- the agents according to the invention are preferably liquid and are suitable for dermal application, in particular as so-called pour-on or spot-on formulations. Other forms of application are possible (see above).
- I. type I pyrethroids such as permethrin: 15-75% by weight, preferably 33-55% by weight
- Type-U pyrethroids such as e.g. Cypermethrin: 1 - 20 wt .-%, preferably 5 - 15 wt .-%.
- Non-ester pyrethroids such as e.g. Etofenprox, silafluofen: 15-75% by weight, preferably 40-60% by weight.
- Natural pyrethrins e.g. Pyrethrin I, Jasmolin I, Cinnerin I, Pyrethrin II, Jasmolin JJ, Cinnin JJ: 25-75% by weight, preferably 30-50% by weight.
- agents which can be used according to the invention contain an active ingredient from the class of nicotinic agonists V-VII in the following amounts:
- Neonicotinoids with 1 - 25 wt .-%, preferably 5 - 15 wt .-%. Examples include: imidacloprid, thiacloprid, clothianidin, nitenpyram, dinotefuran,
- VE Spinosyn with 1 - 25 wt .-%, preferably 5 - 15 wt .-%. Examples include: spinosad, butyl-spinosad.
- agents which can be used according to the invention generally contain customary solvents and spreading agents and, if appropriate, customary auxiliaries.
- the percentages by weight are based on the total weight. -
- Type I pyrethroids are e.g. Allethrin, Bioallethrin, Permethrin, Phenothrin, Resmethrin, Tetramethrin.
- Type JJ pyrethroids are e.g. alpha-cypermethrin, cyfluthrin, cyhalofhrin, cypermethrin, deltamethrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate.
- Non-ester pyrethroids are e.g. Etofenprox, Silafluofen.
- Natural pyrethrins include pyrethrin I, pyrethrin JJ, cinerine I, cinerine U, Jasmolin I, Jasmolin ⁇
- the neonicotinoids are preferably named.
- Neonicotinoids are to be understood in particular as meaning compounds of the formula (I):
- R is hydrogen, optionally substituted radicals of the group acyl, alkyl, aryl, aralkyl,
- A is a monofunctional group selected from the group consisting of hydrogen, acyl, alkyl, aryl or is a bifunctional group which is linked to the radical Z;
- E is an electron-withdrawing radical
- Rest Z can be linked
- Z is a monofunctional group from the series alkyl, -O-R, -S-R,
- R is the same or different radicals and has the abovementioned meaning
- Z is a bifunctional group linked to the radical A or the radical X.
- R is hydrogen and optionally substituted radicals from the series acyl
- Acyl radicals which may be mentioned formyl, (C ⁇ -8 alkyl) carbonyl, (C 6 - ⁇ o-aryl) -carbonyl, (C 1-8 - alkyl) sulfonyl, (C 6 . ⁇ 0 aryl) sulfonyl, (. C ⁇ 8 alkyl) - (C 6- ⁇ 0 aryl) -phosphoryl, which may in turn be substituted.
- alkyl may be mentioned C M0 alkyl, in particular C M alkyl, in particular methyl, ethyl, 'i-propyl, se ⁇ - or t-butyl, which in turn may be substituted.
- Aryl is in particular C ⁇ -io-aryl, examples being phenyl, naphthyl, in particular phenyl.
- Aralkyl particular (C 6 ⁇ 0 aryl) - (C ⁇ -4 alkyl), as examples may be mentioned phenylmethyl, phenethyl.
- heteroaryl may be mentioned heteroaryl having up to 10 ring atoms and N, O, S in particular N as heteroatoms.
- thienyl furyl, thiazolyl, imidazolyl, pyridyl, benzthiazolyl.
- Heteroarylalkyl is especially heteroaryl (C 1-4 alkyl) wherein heteroaryl is as defined above. Examples which may be mentioned are heteroarylmethyl, heteroarylethyl having up to 6 ring atoms and N, O, S, in particular N as heteroatoms.
- Heterocyclyl is in particular an unsaturated but not aromatic or saturated heterocycle having up to 6 ring atoms containing up to 3 heteroatoms selected from N, O, S, for example tetrahydrofuryl.
- Heterocyclylalkyl is in particular heterocyclyl-C 2 alkyl, for. B.: Tetrahydrofuranyl methyl and tetrahydrofuranylethyl.
- Haloalkyl having preferably 1 to 4, in particular 1 or 2 carbon atoms and preferably 1 to 5, in particular 1 to 3 halogen atoms, wherein the halogen atoms are identical or different and are halogen atoms, preferably fluorine, chlorine or bromine, especially fluorine, such as trifluoromethyl; hydroxy; Halogen, preferably fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine; cyano; nitro; amino; Monoalkyl and dialkylamino having preferably 1 to 4, in particular
- Alkylamino such as chloropyridylamino and chloropyridylmethylamino.
- 'A particularly preferably represents hydrogen and optionally substituted radicals from the series acyl, alkyl, aryl, which preferably have the meanings given for R.
- A is also a bifunctional group. Mention may be optionally substituted alkylene having 1-4, in particular 1-2 C atoms, wherein as substituents mentioned above substituents may be mentioned and wherein the alkylene groups may be interrupted by heteroatoms from the series N, O, S.
- heterocyclic ring may contain another 1 or 2 identical or different heteroatoms and / or hetero groups.
- heteroatoms are preferably oxygen, sulfur or nitrogen and hetero groups N-alkyl, wherein alkyl, N-alkyl group preferably contains 1 to 4, in particular 1 or 2 carbon atoms.
- alkyl methyl, ethyl, n- and i-
- the heterocyclic ring contains 5 to 7, preferably 5 or 6 ring members.
- heterocyclic ring examples include pyrrolidine, piperidine, piperazine, hexamethyleneimine, hexahydro-1,3,5-triazine, morpholine and oxadiazine, which may optionally be substituted by methyl.
- E is an electron-withdrawing radical, in particular NO 2, CN, haloalkylcarbonyl such as halogeno-C 1-4 -alkylcarbonyl having 1 to 9 halogen atoms, in particular COCF 3, and also C 1-4 -alkylsulfonyl and halogeno-C 1-4 -alkylsulfonyl having 1 to 9 halogen atoms, in particular SO 2 CF 3, be mentioned.
- haloalkylcarbonyl such as halogeno-C 1-4 -alkylcarbonyl having 1 to 9 halogen atoms, in particular COCF 3
- Z is optionally substituted radicals alkyl, -OR, -SR, -NRR, where R and the
- heterocyclic ring may contain another 1 or 2 identical or different heteroatoms and / or hetero groups.
- heteroatoms are preferably oxygen,
- N-alkyl Sulfur or nitrogen and as hetero groups N-alkyl, wherein the alkyl or N-alkyl group preferably contains 1 to 4, in particular 1 or 2 carbon atoms.
- alkyl methyl, ethyl, n- and i-propyl and n-, i- and t-butyl may be mentioned.
- the heterocyclic ring contains 5 to 7, preferably 5 or 6 ring members.
- heterocyclic ring examples include pyrrolidine, piperidine, piperazine,
- compounds which can be used according to the invention are compounds of the general formulas (JJ), (HI) and (IV):
- n 1 or 2
- n 0, 1 or 2
- Subst. Represents one of the abovementioned substituents, in particular halogen, especially chlorine,
- nicotinic agonists from the group of neonicotinoids
- other nicotinic agonists can also be used according to the invention.
- spinosyn A examples which may be mentioned here are compounds from the group of spinosyns, in particular spinosyns A and D. * Spinosyn A
- spinosyns here are understood synthetic and semi-synthetic derivatives of natural spinosyns or derivatives derived from genetically modified strains of e.g. Saccharopolyspora species are obtained, as described in WO 02/77004 and WO 02/77005, the documents mentioned are expressly incorporated by reference.
- nicotinic receptor agonist-active compounds which can also be successfully combined with Group 1 compounds are, for example, nicotine or nithiazine
- the repelling effect as well as the short-contact mortality of the combination of active substances from the group of nicotinic agonists used in combination with active substances of the group of pyrethroids / pyrethrins is surprisingly better than expected from the effects of the individual components.
- the application rates of active ingredient can be reduced and the long-term effect can be increased. Their application therefore brings economic and environmental benefits.
- the combinations used in the invention are eminently suitable for use in parasitic defense and to prevent transmission of pathogens transmitted by such parasites.
- the parasites can be directly on humans or animals or in the environment are repulsed.
- the combination of active substances mentioned can also be used in the protection of materials, namely for keeping arthropods away from places and materials where they are undesirable.
- Anoplura e.g. Haematopinus spp., Linognathus spp., Solenopotes spp., Pediculus spp., Pthirus spp .;
- siphonaptera e.g. Ctenocepha Kdes spp., Echidnophaga spp., Ceratophyllus spp., Pulex spp.
- metastigmata e.g. Hyalomma spp., Rhipicephalus spp., Boophilus spp., Amblyomriia spp., Haemaphysalis spp., Dermacentor spp., Ixodes spp., Argas spp., Ornithodoras spp., Otobius spp .;
- mesostigmata e.g. Dermanyssus spp., Omithonyssus spp., Pneumonyssus spp.
- astigmata e.g. Acarus spp., Myocoptes spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Neoknemidocoptes spp. Cytodites spp., Laminosioptes spp.
- the agents are used for the repellency of arthropods, preferably ticks, fleas, mosquitoes and flies in animals, in particular in warm-blooded animals.
- Animals are, for example, breeding or livestock: mammals such as cattle, horses, sheep, pigs, goats, camels, water buffalo, donkeys, rabbits, fallow deer, reindeer, fur animals such as mink, chinchilla, raccoon; Birds, such as chickens, geese, turkeys, ducks, and ostriches.
- mice are laboratory and experimental animals, such as Mice, rats, guinea pigs, golden hamsters, dogs and cats.
- hobby animals such as e.g. in dogs and cats.
- the effect of the agents according to the invention may not only occur directly on the animal but also to a corresponding degree in its environment.
- agents used according to the invention may contain, in addition to the abovementioned active ingredients, additional suitable active ingredients.
- growth-inhibiting agents and synergists e.g. Pyriproxyfen ⁇ 2- [l-methyl-2- (4-phenoxyphenoxy) -ethoxy] -pyridines CAS No .: 95737-68-1 ⁇ , methoprene [(E, E) -1-methylethyl-1-methoxy-3, 7,1-l-trimethyl-2,4-dodecadienoate CAS No .: 40596-69-8] and triflumuron ⁇ 2-chloro-N - [[[4- (trifluoromethoxy) phenyl] amino] carbonyl] benzamide CAS No .: 64628-44-0 ⁇ .
- repellent-acting substances such as DEET (diethyltoluamide), Bayrepel® (CAS name: 1-piperidinecarboxylic acid, 2- (2-hydroxyethyl) -, 1-methyl-propyl ester), 2- ( Octylthio) ethanol or 3- (N-acetyl-N-butylamino) propionic acid, ethyl.
- the application to the animal is usually directly or in the form of suitable preparations dermal.
- the repellent mechanism of the pyrethroids / pyrethrins requires contact with the active ingredient, it is advisable to distribute the active ingredients on the entire surface to be protected, for example on all body parts of the treated animals.
- skin penetration of the active ingredients is rather disadvantageous, since the active substances penetrated into the skin are no longer available for the repellent effect.
- the dermal application takes place, for example, in the form of spraying or pouring on and spot-on.
- Suitable preparations are:
- Emulsions and suspensions, semi-solid preparations are Emulsions and suspensions, semi-solid preparations;
- Solid preparations such as powders, premixes or concentrates, granules, pellets, aerosols and active substance-containing shaped bodies.
- Suitable solvents include: Physiologically acceptable solvents such as water, alcohols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methylpyrrolidone, 2-pyrrolidone and mixtures thereof.
- the active compounds can also be dissolved in physiologically tolerated vegetable or synthetic oils.
- Solubilizers which promote the dissolution of the active ingredient in the main solvent or prevent it from precipitating may be mentioned as solubilizers.
- solubilizers examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.
- Preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol.
- Solutions can be applied directly. Concentrates are applied after dilution to the concentration of use.
- Solutions can be applied to the skin, brushed, rubbed, sprayed on or sprayed onto the skin.
- Thickeners are: inorganic thickeners such as bentonites, colloidal silicic acid, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.
- Gels are applied to the skin or brushed or incorporated into body cavities. Gels are made by preparing solutions as described in the injection solutions have been added with so much thickener that a clear mass with ointment-like consistency arises.
- the thickeners used are the thickeners specified above.
- Pour-on formulations are infused or sprayed onto limited areas of the skin, the active ingredient penetrating the skin and acting systemically.
- Pour-on formulations are prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, more. Excipients such as dyes, absorption-promoting substances, antioxidants, light stabilizers, adhesives added.
- a solvent may be mentioned: 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 mono-butyl ether, ketones such as acetone, Methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as n-methylpyrrolidone, n-butyl or n-octylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone
- Dyes are all animal-approved dyes that may be dissolved or suspended.
- Absorption promoting substances are e.g. DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils or their copolymers with polyethers, fatty acid esters, triglycerides, fatty alcohols.
- spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils or their copolymers with polyethers, fatty acid esters, triglycerides, fatty alcohols.
- Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.
- Sunscreen agents are e.g. Novantisol acid.
- Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.
- Emulsions are either water-in-oil type or oil-in-water type. They are prepared by dissolving the active ingredient either in the hydrophobic or in the hydrophilic phase and this with the aid of suitable 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 may be mentioned: paraffin oils, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric acid biglycerid, triglyceride mixture with vegetable fatty acids of chain length Cg. ⁇ Or other ' specially selected natural fatty acids, partial glyceride mixtures saturated or unsaturated fatty acids which may also contain hydroxyl groups, mono- and diglycerides of Cg / C ⁇ Q fatty acids.
- Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length Ci g. ⁇ g, isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohols, the chain length Ci2- ig, isopropyl stearate, oleic acid oleate, oleic acid ethyl ester, ethyl oleate, ethyl lactate, waxy fatty acid esters such as artificial duck flake gland fat, dibutyl phthalate, diisopropyl adipate, the latter related ester mixtures, among others
- Fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.
- Fatty acids e.g. Oleic acid and its mixtures.
- hydrophilic phase may be mentioned:
- Alcohols such as e.g. Propylene glycol, glycerol, sorbitol and their mixtures.
- emulsifiers nonionic surfactants, e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ethers;
- nonionic surfactants e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ethers;
- ampholytic surfactants such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin;
- anionic surfactants such as Na lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;
- cationic surfactants such as cetyltrimethylammonium chloride.
- Other auxiliaries which may be mentioned are: viscosity-increasing and emulsion-stabilizing substances such as carboxymethylcellulose, methylcellulose 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, col - loidal silicic acid or mixtures of the listed substances.
- viscosity-increasing and emulsion-stabilizing substances such as carboxymethylcellulose, methylcellulose 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, col - loidal silicic
- Suspensions are prepared by suspending the active ingredient in a carrier liquid optionally with the addition of further adjuvants such as wetting agents, dyes, absorption-promoting substances, preservatives, antioxidants light stabilizers.
- carrier liquids As carrier liquids, all homogeneous solvents and solvent mixtures may be mentioned.
- Suitable wetting agents are the surfactants specified above.
- Semi-solid preparations differ from the suspensions and emulsions described above only in their higher viscosity.
- the active compound is mixed with suitable excipients, if appropriate with the addition of auxiliaries, and brought into the desired form.
- Suitable carriers are all physiologically compatible solid inert substances.
- inorganic and organic substances are used.
- Inorganic substances are e.g. Common salt, carbonates such as calcium carbonate, bicarbonates, aluminum oxides, titanium oxide, silicas, clays, precipitated or colloidal silica, phosphates.
- Organic substances are e.g. Sugar, cellulose, food and feed such as milk powder, animal meal, cereal flours and meals, starches.
- Excipients are preservatives, antioxidants, dyes, which have already been mentioned above.
- Suitable excipients are lubricants and lubricants such as e.g. Magnesium stearate, stearic acid, talc, bentonites, disintegrants 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 e.g. Magnesium stearate, stearic acid, talc, bentonites, disintegrants 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 compounds may also be present in the preparations in admixture with synergists or with other active ingredients which act against pathogenic endoparasites.
- N-methylpyrrolidone in a proportion of 27.5 to 62.5 wt .-%, preferably 35 to 50 wt .-%, particularly preferably 40 to 45 wt .-%.
- Antioxidants in a proportion of 0 - 0.5 wt .-%, preferably 0.05 - 0.25 wt .-%, particularly preferably 0.05 -0.15 wt .-%.
- antioxidants are ' phenolic antioxidants such as Butylhydr ⁇ xytoluol, Butylhydroxyanisol, tocopherol.
- Organic acid in a proportion of 0 - 0.5 wt .-%, preferably 0.05 - 0.25 wt .-%, particularly preferably 0.05 -0.15 wt .-%.
- Suitable for use are all pharmaceutically acceptable organic acids, especially carboxylic acids, e.g. Citric acid, tartaric acid, lactic acid, succinic acid and malic acid.
- the organic acids are citric acid and malic acid. Most preferred is citric acid.
- Their amount can be varied in particular in the range 0.05 to 0.25 wide. The amounts in the range 0.075-0.15% are again particularly preferred.
- Co-solvent amounts in a proportion of 2.5 to 10 wt .-%, preferably 2.5 to 7.5 wt .-%, particularly preferably 3.5 to 6.0 wt .-%.
- Suitable co-solvents are organic solvents having a boiling point> 80 ° C. and a flame point> 75 ° C.
- the co-solvents have a spreading effect.
- attention is drawn to higher-boiling aliphatic and aromatic alcohols, aliphatic polyethers, aliphatic and / or aromatic esters, cyclic and / or acyclic carbonates.
- Co-solvents are preferably aliphatic acyclic or cyclic ethers or polyethers and fatty acid esters, in particular triglycerides used.
- Examples include ether or polyether, for example from the series diethylene glycol monoethylther, dipropylene glycol monomethyl ether, tetrahydrofurfuryl alcohol and. Tetrahydrofurfuryl ethoxylate, the latter two being particularly preferred; Fatty acid esters and triglycerides, for example isopropyl myristate, Miglyol 810, Miglyol 812, Miglyol 818, Miglyol 829, Miglyol 840 and Miglyol 8810 (for the definition of the Miglyols, see, for example, HP Fiedler Lexikon der Hilfsstoffe für Pharmazie, Kosmetik und Nachbaring withe, pages 1008-1009, Vol 2, Edito Cantor Verlag Aulendorf (1996)).
- the agents modified with the mentioned cosolvents are distinguished by their very good skin and eye compatibility, excellent biological activity and by their favorable low-temperature behavior in the usual single-dose application tubes.
- compositions of the invention may contain other conventional pharmaceutically acceptable excipients. Examples which may be mentioned as such are: spreading agents and surfactants.
- Spreading agents are, for example, spreading oils such as adipic di-2-ethylhexyl ester, isopropyl myristate, dipropylene glycol pelargonate, cyclic and acyclic silicone oils such as dimetikone and also their copolymers and terpolymers with ethylene oxide, propylene oxide and formalin, fatty acid esters, triglycerides, fatty alcohols.
- spreading oils such as adipic di-2-ethylhexyl ester, isopropyl myristate, dipropylene glycol pelargonate, cyclic and acyclic silicone oils such as dimetikone and also their copolymers and terpolymers with ethylene oxide, propylene oxide and formalin, fatty acid esters, triglycerides, fatty alcohols.
- nonionic surfactants e.g. polyoxyethylated castor oil, polyoxyethylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ethers;
- ampholytic surfactants such as di-Na-N-lauryl-.beta.-imidodipropionate or lecithin;
- anionic surfactants such as Na lauryl sulfate, fatty alcohol ether sulfates, mono / dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;
- cationic surfactants such as cetyltrimethylammonium chloride.
- the agents used according to the invention can be prepared by customary processes, for example by mixing the active ingredients with stirring with the other constituents and preparing a solution. This can optionally be filtered.
- plastic tubes are suitable for filling.
- the preferred application volumes for the formulations described in WO 02/087338 are 0.075-0.25 ml / 1.0 kg [body weight of the animal to be treated], preferably 0.1-0.15 ml / 1.0 kg [body weight of the animal to be treated].
- a homogeneous spot-on solution consisting of
- Example 6 A homogeneous spot on solution consisting of
- Example 11 A homogeneous spot-on solution consisting of
- Example 14 A homogeneous spot on solution consisting of
- Example 19 A homogeneous spot on solution consisting of
- Example 23 A homogeneous spot on solution consisting of
- Example 26 A homogeneous spot on solution consisting of
- Example 31 A homogeneous spot-on solution consisting of
- Example 34 A homogeneous spot on solution consisting of
- Diacloden (thiamethoxam) from Syngenta AG 39.8 g N-methylpyrrolidone 0.1 g citric acid 0.1 g BHT 5.0 g tefrahydrofurfuryl ethoxylate
- Example 40 A homogeneous spot on solution consisting of
- Each test value is carried out with 30 ticks. All ticks are tested one after the other in the same apparatus. For each test series, a pure solvent test without repellent is performed to test the basal activity of the ticks. As a limit activity for the performance of a test, the change of at least 70% of the ticks on the drum is considered. For each test product a separate test drum is used. After each test series, all equipment used is thoroughly cleaned.
- a standard drum and attachment surface was used (Dautel et al., 1999).
- the attachment area was 1-3 mm above the drum surface.
- the distance between the glass rod of 2 mm diameter and the attachment surface was between 1 and a maximum of 1.5 mm.
- the rotation time of the drum was between 3.9 and 4.1 s / rev corresponding to 7.66 - 8.05 cm / s relative to the tick.
- the surface temperature at the adherend surface was between 34.6 and 35.5 ° C.
- Room temperature and ambient humidity were between 19.1 - 22.3 ° C and 43.4 - 78.1% rh R. sanguineus:
- the rotation time of the drum was between 5.6 and 6.0 s / rev corresponding to 5.23 - 5.61 cm / s relative to the tick.
- the surface temperature at the adherend surface was between 35 and 36 ° C.
- Room temperature and ambient humidity were between 19.4 - 23.5 ° C and 59.1 - 79.5% r.h.
- Acetone was used as solvent and for the dilutions in all experiments.
- the application was carried out 1-2 hours before the start of the experiment to allow enough time for evaporation of the solvent.
- the active ingredients were applied to the filter papers with a disposable pipette. An even distribution on the larger surface of the molton cloth was achieved by means of a spray apparatus under nitrogen pressure. The exact applied volume was determined by back weighing.
- ticks Only those ticks were used in the test that actively climbed to the top in a glass tube and swiftly switched to a badger hair brush (0 or 1) used to transfer the ticks. These ticks were placed head to drum on the glass rod at a distance of 1.5 cm (I. ricinus) or 2.5-4 cm (R. sanguineus) to the tip of the glass rod. The trial period started as soon as a tick crossed the 1 cm (I. ricinus) or the 2 cm (R. sanguineus) mark on the glass rod. Ticks that fell off the brush or dropped off the glass rod before marking were not counted. The following time periods were recorded by stopwatch:
- a total repelling effect relative to the control was calculated by adding together all the ticks that did not go towards the drum, which did not change to the drum and dropped from the attachment surface. All of these ticks were considered repelled.
- the repellent effect is calculated as follows:
- R is the repellent effect
- pt is the percentage of non-repelled ticks
- pc is the percentage of non-repelled control ticks.
- the first value refers to the amount of imidacloprid, the second to the amount of permethri ⁇
- Example 1 surprisingly shows a significantly stronger repellent effect than the standard (Exspot® contains permethrin as the sole active ingredient). Ticks on the standard (Exspot® contains permethrin as the sole active ingredient).
- the first value refers to the amount of imidacloprid, the second to the amount of permethrin
- Example 1 Another sign of the improved repellent effect is the delayed passage from the glass rod to the drum. Again, ticks in Example 1 compared to the standard by an average of a factor of 3 extended time interval. The standard is in the area of a control.
- Example 1 Compared to the respective control, the formulation of Example 1 according to the invention shows a 100% repellent effect in the relevant dose range for a topically uniformly distributed formulation after spot-on application. Surprisingly, the known commercial product is not able to repel all ticks under the same conditions. Results from Repellent Tests with Ixodes ricinus Ticks - Comparison with the Prior Art (Exspot®, Schering-Plow Co.)
- the example according to the invention surprisingly shows a significantly improved repellent effect.
- the example of the invention shows repellency in the same range as in the higher dosages, while the curve of the repellent effect in the prior art has already decreased by 6 times.
- Formulations according to the invention thus show, at the same application rate, a significantly improved repellent effect against ticks over the prior art in the important parameters of transference sensitivity to the surface, duration of residence on the surface and in effectiveness at lower dosages.
- Ticks that were able to coordinate movement were considered alive.
- Ticks that made only small movements with the tarsen or mouthparts or were unable to walk were considered moribund.
- Ticks that remained immobile after C02 stimulus or high-light pulse were considered dead.
- the first value refers to the amount of imidacloprid, the second to the amount of permethrin
- the formulations according to the invention additionally protect the fact that repelled ticks are already killed even after short contact times of considerably less than 1 minute, and thus further hosts can no longer be attacked by repelled ticks.
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- Tropical Medicine & Parasitology (AREA)
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Abstract
Description
Claims
Priority Applications (17)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
UAA200508125A UA83817C2 (ru) | 2003-01-17 | 2004-01-05 | Репеллент, содержащий комбинацию пиретроида/пиретрина и никотинового агониста |
JP2006500515A JP2006516970A (ja) | 2003-01-17 | 2004-01-05 | 駆除剤 |
SI200431185T SI1587368T1 (sl) | 2003-01-17 | 2004-01-05 | Repelent |
AU2004206720A AU2004206720B2 (en) | 2003-01-17 | 2004-01-05 | Repellent |
EP04700127A EP1587368B1 (de) | 2003-01-17 | 2004-01-05 | Repellentmittel |
US10/541,087 US20060211655A1 (en) | 2003-01-17 | 2004-01-05 | Repellent |
AT04700127T ATE432008T1 (de) | 2003-01-17 | 2004-01-05 | Repellentmittel |
CA2513269A CA2513269C (en) | 2003-01-17 | 2004-01-05 | Repellent |
DE502004009524T DE502004009524D1 (de) | 2003-01-17 | 2004-01-05 | Repellentmittel |
DK04700127T DK1587368T3 (da) | 2003-01-17 | 2004-01-05 | Repellentmiddel |
BR0406788-6A BRPI0406788A (pt) | 2003-01-17 | 2004-01-05 | Agente repelente |
NZ541280A NZ541280A (en) | 2003-01-17 | 2004-01-05 | Use of a pyrethroid or pyrethrin in combination with a nicotinic agonist to repel insects |
MXPA05007246A MXPA05007246A (es) | 2003-01-17 | 2004-01-05 | Agente repelente. |
IL169515A IL169515A (en) | 2003-01-17 | 2005-07-04 | Use of a pyrethroid or pyrethrin in combination with a nicotinic agonist for repelling arthropods |
NO20053811A NO332114B1 (no) | 2003-01-17 | 2005-08-12 | Anvendelse av et pyretroid eller pyretrin samt fremgangsmate for frastotning av artropoder fra varmblodige species. |
HRP20050716AA HRP20050716B1 (hr) | 2003-01-17 | 2005-08-16 | Sredstvo za odbijanje kukaca |
HK06109109.3A HK1088790A1 (en) | 2003-01-17 | 2006-08-16 | Repellent |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10301906A DE10301906A1 (de) | 2003-01-17 | 2003-01-17 | Repellentmittel |
DE10301906.5 | 2003-01-17 |
Publications (1)
Publication Number | Publication Date |
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WO2004064522A1 true WO2004064522A1 (de) | 2004-08-05 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2004/000017 WO2004064522A1 (de) | 2003-01-17 | 2004-01-05 | Repellentmittel |
Country Status (33)
Country | Link |
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US (1) | US20060211655A1 (de) |
EP (1) | EP1587368B1 (de) |
JP (5) | JP2006516970A (de) |
KR (1) | KR20050094435A (de) |
CN (1) | CN100591209C (de) |
AR (1) | AR042898A1 (de) |
AT (1) | ATE432008T1 (de) |
AU (1) | AU2004206720B2 (de) |
BR (1) | BRPI0406788A (de) |
CA (1) | CA2513269C (de) |
CO (1) | CO5640058A2 (de) |
CR (1) | CR7898A (de) |
DE (2) | DE10301906A1 (de) |
DK (1) | DK1587368T3 (de) |
ES (1) | ES2325504T3 (de) |
GT (1) | GT200400005A (de) |
HK (1) | HK1088790A1 (de) |
HR (1) | HRP20050716B1 (de) |
IL (1) | IL169515A (de) |
MX (1) | MXPA05007246A (de) |
MY (1) | MY148978A (de) |
NO (1) | NO332114B1 (de) |
NZ (1) | NZ541280A (de) |
PE (1) | PE20040890A1 (de) |
PL (1) | PL218068B1 (de) |
PT (1) | PT1587368E (de) |
RU (1) | RU2350079C2 (de) |
SI (1) | SI1587368T1 (de) |
TW (1) | TWI358991B (de) |
UA (1) | UA83817C2 (de) |
UY (1) | UY28165A1 (de) |
WO (1) | WO2004064522A1 (de) |
ZA (1) | ZA200505575B (de) |
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-
2003
- 2003-01-17 DE DE10301906A patent/DE10301906A1/de not_active Withdrawn
-
2004
- 2004-01-05 DK DK04700127T patent/DK1587368T3/da active
- 2004-01-05 NZ NZ541280A patent/NZ541280A/en not_active IP Right Cessation
- 2004-01-05 CA CA2513269A patent/CA2513269C/en not_active Expired - Lifetime
- 2004-01-05 DE DE502004009524T patent/DE502004009524D1/de not_active Expired - Lifetime
- 2004-01-05 JP JP2006500515A patent/JP2006516970A/ja active Pending
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