EP1694362A4 - Verbesserte parasitizid-zusammensetzung - Google Patents

Verbesserte parasitizid-zusammensetzung

Info

Publication number
EP1694362A4
EP1694362A4 EP04801110A EP04801110A EP1694362A4 EP 1694362 A4 EP1694362 A4 EP 1694362A4 EP 04801110 A EP04801110 A EP 04801110A EP 04801110 A EP04801110 A EP 04801110A EP 1694362 A4 EP1694362 A4 EP 1694362A4
Authority
EP
European Patent Office
Prior art keywords
composition according
water washable
parasiticide
group
parasiticide composition
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.)
Withdrawn
Application number
EP04801110A
Other languages
English (en)
French (fr)
Other versions
EP1694362A1 (de
Inventor
Kai Kin Lau
Michael Thomas Wilson
Charles Stewart Lowden
Marcus Holdsworth
Brian Desmond Ford
Edward Lionel Bruce Whittem
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.)
Jurox Pty Ltd
Original Assignee
Jurox Pty 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
Priority claimed from AU2003906726A external-priority patent/AU2003906726A0/en
Application filed by Jurox Pty Ltd filed Critical Jurox Pty Ltd
Publication of EP1694362A1 publication Critical patent/EP1694362A1/de
Publication of EP1694362A4 publication Critical patent/EP1694362A4/de
Withdrawn legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0014Skin, i.e. galenical aspects of topical compositions
    • A61K9/0017Non-human animal skin, e.g. pour-on, spot-on
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/34Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/661,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/681,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N49/00Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/16Amides, e.g. hydroxamic acids
    • A61K31/17Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents

Definitions

  • This invention relates to parasiticide compositions, especially water washable liquid compositions for veterinary use.
  • Insecticide and parasiticide compositions are widely used in the veterinary field to deliver active substances in liquid form to animals, particularly farm animals.
  • the insecticide parasiticide compositions may he given to the animal orally (by way of drench) or by application to an external part of the animal. When applied to an external part of the animal the insecticide parasiticide composition is referred to as a "pour-on composition".
  • the desirability of pour-on compositions stems from ease of use, especially when application along with effectiveness is achieved.
  • the essence of a pour-on composition is that it is formulated as a liquid for topical application to the skin, of an animal, such as along the back of the animal.
  • a pour-on composition spreads on the skin so as to deliver effectively th insecticide/parasiticide composition to the animal.
  • Pour-on compositions and compositions used in drenching are applied from an applicator device such as an applicator gun. It is standard practice for farmers to clean the applicator device with water after they have finished administering or applying the insecticide/parasiticide composition to the animal.
  • the active ingredient of the insecticide parasiticide composition is water insoluble and in such a situation die following problem (i) and possibly (ii) occur: (i) the applicator becomes clogged due to crystallisation of the active substance from the insecticide/parasiticide composition; and (ii) a change in the concentration of the active substance administered from the applicator may occur as a result of the active substance crystallising in the applicator and being included in the next dose of insecticide/ parasiticide administered to the animal.
  • Insect growth regulators such as triflumuron, are used to destroy insect larva. Essentially, IGR's prevent the fo ⁇ nation of new chitin during the insects moulting stage.
  • Chitin is the substance that makes up the insects exoskeleton and IGR's act as a chitin synthesis inhibitor by preventing the enzyme necessary to produce chitin from functioning.
  • IGR's are an external parasiticide which prevents the development of immature lice present in the fleece of sheep. Accordingly, IGR's such as trifiumuron are used as active substances in parasiticide compositions but due to the fact that they are water insoluble, the problems noted above are experienced when a parasiticide composition containing IGR's are applied to an animal via an applicator device. More specifically, the applicator becomes clogged due to crystallisation of the IGR from the parasiticide composition.
  • the crystallisation is due to low solubility of IGR in water and limited solvation power of the solvent system in the composition. It would be desirable, therefore, to provide a water washable parasiticide composition containing art IGR. However, given the insolubility of this compound in water, there is a technical difficulty to be met in providing such a composition.
  • Parasiticide compositions containing IGR's are routinely applied to animals whose hide/fur/wool is removed for human use. It is therefore necessary to ensure that the levels of IGR residing, in the hide/fur/wool intended for human contact is at an acceptable level. Additionally, it is particularly desirable that the IGR loading in the waste water from textile scouring plants is also at an acceptable level.
  • the concentration of IGR in human-food products derived from the animal is required to be below a Maximum Residue Limit (MRL) as set by the relevant governing authority in each country.
  • MLR Maximum Residue Limit
  • the inventors are aware of a number of pour-on parasiticides compositions currently on the market that are only able to meet the MRL for tissues after a substantial withholding period has been observed, some being excluded from ever being used in milk producing animals, Having regard to this requirement, it would therefore be desirable to provide a parasiticide composition in which the amount of IGR that can be found in human-food products derived from the animal meets the MRL in a period of time that is less than the withholding period specified for currently available parasiticide compositions.
  • the present inventors have now found a means to provide an improved parasiticide composition based on an insect growth regulator (IGR), that is water washable and is effeetive against lice once applied to an animal and has a low level of IGR residing in the hide, fur, wool and/or consumable portions of the animal after application of the parasiticide composition to the animal. Surprisingly, this has been achieved by including into the parasiticide composition specific amounts of one or more emollients together with one or more solvents.
  • the present invention is directed to a water washable parasiticide composition comprising: 0.01 - 30% w/v of one or more insect growth regulators; 0.01 - 20% w/v of one or more emollients; the balance being one or more organic solvents.
  • the water washable parasiticide composition may further include one or more surfactants.
  • the stable insecticide/parasiticide composition includes one or more synthetic pyrethroids, more preferably about 0.01-5% w/v of one or more synthetic pyrelhroids (SP).
  • SP synthetic pyrelhroids
  • the present invention is directed to a method of treating parasites in on an animal, the method comprising a ⁇ LLtministering to the animal an effective amount of the parasiticide composition according to the first aspect of the invention.
  • an "effective amount of the parasiticide composition” means that the amount of the parasiticide composition of the invention that is administered to the animal must be effective in treating, by way of killing or repelling, the parasites on in the animal.
  • an "effective amount of parasiticide composition” may be achieved using a dose volume that is calculated using (i) the weight of the animal or (ii) the surface area of me animal.
  • the preferred "effective amount of the parasiticide composition” is a dosage volume of about 10-100 mL per :5Q kg of bodyweight of animal.
  • one dose volume of the parasiticide composition may be used to cover a wide range of surface areas within the target species population.
  • Calculating a dose volume for application based on the surface area of an animal rather than its body weight has several advantages. Firstly, it allows the product to be tailored to meet its mode of administration and action. Secondly, the dose regime is simplified for the applicator. Thirdly, it permits the manufacturer to select a dose volume suitable for a pour-on for a defined purpose within a simplified dosage regime. Tables 3 and 4 provide preferred dosage volumes based on (i) the weight of the animal (Table 3) and (ii) the surface area of the animal (Table 4) for different compositions according to preferred embodiments of the first aspect of the invention.
  • the present invention is directed to the use of the parasiticide composition according to the first aspect of the invention in the preparation of a medicament for the treatment of parasites in/on an animal.
  • the present invention is directed to a method of cleaning a device containing a water washable parasiticide composition according to the first aspect of the invention, the method comprising washing the device with an aqueous solution in a manner so as to effectively remove substantially all of the composition from the device.
  • water washable means that when water is added to the parasiticide composition, the insect growth regulator (IGR) forms a coarse emulsion which contains fine crystals of insect growth regulator.
  • the insect growth regulator is preferably selected from one or more of the group consisting of triflumuron, cyromazine, diflubenzuro ⁇ , fluazuron and methoprene and mixtures thereof.. More preferably, the IGR is triflumuron.
  • the IGR is included in the composition in a concentration of about 0.01-30% w/v. In one embodiment, the preferred concentration of IGR is in the range of about 0.1-20%w/v, most preferably about 0.1-10% w/v, even more preferably about- 0.1-5% w/v. In another embodiment, the preferred concentration of IGR is about 0.1-30%w/v, more preferably about 2- 30%w/v.
  • emollients may be used in the parasiticide composition of the present application. These include but are not limited to one or more of the following: fatty acid esters such as cetyl acetate, cetyl palmitate, myristic acid isopropyl ester, palmitic acid isopropyl ester, steric acid isopropyl ester, cetyl lactate (e.g. Pelemol CL, Wickenol 507), acetylated lanoline (e.g. Ritacetyl), cetyl palmitate (e.g. Cutina CP), octyl stearate (e.g.
  • fatty acid esters such as cetyl acetate, cetyl palmitate, myristic acid isopropyl ester, palmitic acid isopropyl ester, steric acid isopropyl ester, cetyl lactate (e.g. Pelemol CL, Wickenol 507), acetylated lanoline (
  • Cetiol 868 isooctyl stearate, lauric acid hexyl ester (e.g. Cetiol A), butyl adipate, dibutyl adipate (e.g. Cetiol B), octyl palmitate and myrtistyl myristate (e.g. Cegesoft C and Cetiol MM), myristyl lactate (e.g. Cetiol 868), glycol isostearate, caprylic acid ester and capric acid ester; a mixture of glycol distearate, laureth-4 and cocamidopropyl betaine (e.g.
  • Euperian PK 3000 a mixture of sodium laureth sulfate, glycol distearate and cocamide MEA (e.g. Euperian PK 771); a mixture of glycol distearate, sodium laureth sulfate, cocamide MEA and Laureth-9 (e.g. Euperian PK 810); a mixture of triethylene glycol distearate and sodium laurcth sulfate (e.g Euperian PK 900); long chain fatty alcohols such as n-octyl dodecanol (e.g. Eutanol G), cetyl alcohol, cetyl steryl alcohol, oleyl alcohol; lanolin oil and derivatives (e.g.
  • Lantrol HP, Ritalan Lantrol HP, Ritalan
  • triglycerides such as captylic capric triglyceride (e.g. Myritol 318) and glycol isostearate
  • sterols such as beta-sitosterol, campesterol. stigmasterol (e.g Avocardin); distilled wool wax alcohols (e.g. Super Bartoian) and rnixtures thereof.
  • the fatty acid esters have an alcohol component with a chain length of CI - C2 or C4-C18 and/or an acid component with a chain length of C4 - C13 or C15 - C30.
  • the fatty acid esters have an alcohol component with a chain length of C4-C18, such as cetyl acetate, cetyl palmitate, lanoline acetate; and/or an acid component with a chain length of CS - C13 or C15 - C24, such as palmitic acid isopropyl ester, stoic acid isopropyl ester, lauric acid hexyl ester (e.g. Cetiol A), caprylic acid ester and capric acid ester.
  • C4-C18 such as cetyl acetate, cetyl palmitate, lanoline acetate
  • an acid component with a chain length of CS - C13 or C15 - C24 such as palmitic acid isopropyl ester, stoic acid isopropyl ester, lauric acid hexyl ester (e.g. Cetiol A), caprylic acid ester and capric acid ester.
  • the fatty alcohols have a chain length of C8 - C18, such as cetyl alcohol, cetyl steryl alcohol, oleyl alcohol, octyl dodecanol.
  • the triglycerides have a vegetable fatty acid component with a chain length of C8-C12, such as caprylic/capric triglyceride (e.g. Myritol 318) and glycol isostearate.
  • the emollient is selected from one or more of the following: fatty acid esters having an alcohol component with a chain length of CI - C2 or C4-C18; fatty acid esters having an acid component with a chain length of C4 - C13 or C15 - C30; a mixture of glycol distearate, laureth-4 and cocamidopropyl bctaine; a mixture of sodium laureth sulfate, glycol distearate and cocamide MEA; a mixture of glycol distearate, sodium laureth sulfate, cocamide MEA and Laureth-9; a mixture of triethylene glycol distearate and sodium laureth sulfate; long chain fatty alcohols; lanolin oil; triglycerides; sterols; 5 distilled wool wax alcohols and mixtures thereof
  • the one or more emollients is selected from fatty acid esters having an alcohol component with a chain length of CI - C2
  • a mixture of triethylene glycol distearate and sodium lauretli sulfate e.g Euperian PK 900
  • long chain fatty alcohols of chain length C8 - C18 such as cetyl alcohol, cetyl steryl alcohol, oleyl alcohol; octyl dodecanol; lanolin oil and derivatives thereof (e.g. Lantrol HP, Ritalan); triglycerides having a vegetable fatty acid component with a chain length of C8-C12 such as caprylic/capric triglyceride (e.g, Myritol 318) and
  • the one or more emollients are selected from the group consisting of lanolin acetate, cetyl acetate, lauric acid hexyl ester; caprylic capric triglyceride, palmitic acid isopropyl ester, cetyl alcohol and mixtures 5 thereof.
  • the one or more emollients may be combined with one or more surfactants (e.g. Solulan 98) .
  • the one or more emollients will be used in a concentration of about 0.01-20 %w/v.
  • the preferred concentration of emollient is about 0.02 - 10%w/v, more preferably about 0.05-5%w/v.
  • the preferred concentration of emollient is about 0.02 - 10%w/v, more preferably about 0.05-5%w/v.
  • emollient concentration is about 0.1-20%w/v, more preferably 0.5- 20%w/v. It has surprisingly been found that the addition of an emollient into the IGR containing parasiticide composition of the present invention provides both a low residue and water washable IGR composition. In a preferred embodiment of the
  • the inventors have found that the emollient reduces the crystal size of the triflumuron during washing with water in such a way that the applicator device will not clog and can be reused again.
  • One or more organic solvents are included in the composition of the invention.
  • the one or more organic solvents are selected from the group consisting of alcohols such as aliphatic and aromatic alcohols; glycols; aliphatic and/or aromatic aldehydes; ketones; aliphatic and/or aromatic hydrocarbons; polyols; glycol ethers; glycol ether acetate; CI - C8 alkyl pyrrolidones; aliphatic and/or aromatic esters and mixtures thereof.
  • alcohols such as aliphatic and aromatic alcohols
  • glycols include but are not limited to methanol, butanol and isopropyl alcohol.
  • aromatic alcohols include but are not limited to benzyl alcohol.
  • glycols include but are not limited to polyethylene glycols and polypropylene glycols.
  • Examples of aliphatic hydrocarbons include but are not limited to octane.
  • Examples of aromatic hydrocarbons include but are not limited to toluene, xylene and blends such as ⁇ Solvesso 150 and Solvesso 200.
  • Examples of ketones include but are not limitation to acetone, 3-buten-2-one, butanonc and cyclohexanone.
  • Examples of glycol ethers include but are not limited to dipropyleneglycol monomethyl ether, butyl icinol and butyl di-icinol. Examples of C ⁇ -
  • C a alkyl pyrrolidones include but are not limited to N-methyl pyrrolidone, l-octyl-2- pyrrolidinone and lauryl pyrrolidone.
  • aromatic esters include but are not limited to benzyl benzoate.
  • aliphatic esters include but are not Umited to methyl acetate, ethyl acetate.
  • the organic solvent is selected from one or more of the group consisting of dipropyleneglycol monomethyl ether, N-methyl pyrrolidone, benzyl alcohol, toluene, xylene, benzyl benzoate, cyclohexanone, butyl di-icinol and ethyl acetate and mixtures thereof.
  • the organic solvent forms the balance of the composition.
  • the total concentration of the solvent may be in the range of 10-99.9% w/v.
  • the concentration used is in the range of 20-99.5% most preferably 30-99.5% w/v.
  • a preferred solvent is a mixture of dipropyleneglycol monomethyl ether and N-methyl pyrrolidone.
  • the solvent is benzyl alcohol, Solvesso 150 or Solvesso 200.
  • the primary solvent is preferably selected from N- methyl pyrrolidone (NMP), Solvesso 150 and Solvesso 200; and the secondary solvent is selected from benzyl benzoate, cyclohexanone, butyl di-icinol, dipropyleneglycol monomethyl ether ( PM) and ethyl acetate.
  • the parasiticide composition optionally includes one or more surfactants.
  • the one or more surfactants may be selected from non-ionic, anionic, cationic or amphoteric surfactants and mixtures thereof. Preferably, one or more non-ionic and/or one or more anionic surfactants are used.
  • the surfactant may also function as a spreading agent.
  • One or more non-ionic surfactants maybe selected from the group consisting of C8-C10 alkylphenol ethoxylates, such as ethoxylated nonylphenol; C9-C17 alcohol ethoxylates; C8-C20 alkyl amine ethoxylates; castor oil ethoxylates; lanolin alcohol ethoxylates; sorbitan fatty acid ester ethoxylates; sorbitan fatty acid esters; alkyl aryl sulphonates and mixtures thereof.
  • the C8-C10 alkylphenol ethoxylates preferably contain from 2 to 100 moles of ethylene oxide and may be selected from but not limited to the commercially available Teric N Series products, such as those identified as Teric N9, Teric N20 and Teric N100.
  • the C9-C17 alcohol ethoxylates preferably contain from 2 to 25 moles of ethylene oxide and may be selected from but not limited to the commercially available products identified as Teric 9A2 and Teric 16A16.
  • the C8-C20 alkyl amine ethoxylates preferably contain from 5 to 20 moles of ethylene oxide and may be selected from but not limited to the commercially available products identified as Teric 13M15 and Teric 18M20.
  • the castor oil ethoxylates preferably contain from 5 to 60 moles of ethylene oxide and may be selected from but not limited to the commercially available products identified as Cremophor EL, Acconon CA-5 and Teric 380.
  • LThe lanolin alcohol ethoxylates preferably contain from 5 to 40 moles of ethylene oxide and may be selected from but not limited to the commercially available products identified as Polycol 5 and Polycol 40.
  • the sorbitan fatty acid ester ethoxylates preferably contain 4 to 20 moles of ethylene oxide and may be selected from but not limited to Polysorbate 20, Polysorbate 60 and Polysorbate 80.
  • the sorbitan fatty acid esters preferably have a chain length of C18-C60 and more preferably have an HLB of 2-9 and may be selected from but not limited to sorbitan monoisostearate, sorbitan monostearate, Hodag SML and Span 25.
  • the nonionic surfactant is one or more sorbitan fatty acid ester ethoxylates (e.g. Polysorbate 80)
  • Anionic surfactants may be selected from the group consisting of C9 - C13 alkyl benzene sulphonates such as sodium dodecylbenzenesulphonate and C9 - C13 alkyl sulphates such as sodium lauryl sulphate and mixtures thereof.
  • the surfactant is present in the parasiticide composition in a concentration of about 0.005 - 30%w/v.
  • the concentration of surfactant is preferably in the range of about 0.01 - 20% w/v, more preferably about 0.02-10% and most preferably about 0.05-5% w/v.
  • the concentration of surfactant is preferably about 0.1-30%w/v, more preferably about 0.5- 30%w/v.
  • SP synthetic pyrethroids
  • the synthetic pyrethroid is preferably selected from one or more of the group consisting of alphacypermetbrin, cypermethrin, deltamethrin, permethrin, bifenthrin and cyflutiirin and mixtures thereof
  • the SP may be included in the composition in a concentration of about 0.01-5.0% w/v, more preferably about 0.075-5%w/v. From preliminary results, the present inventors believe that the inclusion of one or more SP's in the composition of the present invention will also result in a low level of SP residing in the hide, fur, wool and/or consumable portions of the animal after application of the parasiticide composition to the animal.
  • the composition according to the invention may further include one or more fragrances.
  • Fragrances may be in the form of essential oils including but not limited to eucalyptus oil, tea tree oil, orange oil, garlic oil and clove oil or terpenes such as d- limonene, ⁇ -pinene, ⁇ -pin ⁇ ne, ⁇ -myrcene and terpinolene and mixtures thereof.
  • fragrances are present in a range of about 1 - 5% more preferably, about 0:5 - 5%
  • the availability of insect growth regulators, emollients, solvents, surfactants, synthetic pyrethroids and fragrances is shown in Tables 11-16,
  • the composition may further include additives which are commonly used in insecticide/parasiticide compositions including but not limited to dyes and oils such as hydrocarbon oils, mineral oils, vegetable oils and mixtures thereof,
  • the compositions of the invention may be produced by dissolving one or more
  • compositions of the invention may be produced by varying the order in which the ingredients are combined.
  • the composition according to the first aspect of the invention may be in the form of an emulsifiable concentrate which may be further diluted with water before use.
  • a composition includes one or more IGR's in an amount of about
  • composition of the invention in the form of an emulsifiable concentrate includes one or more surfactants in an amount of about 0.1- 30%w/v, preferably 0.5-30%w/v.
  • the composition according to the present invention before or after dilution with water, may be given externally to the animal as a pour-on, spray-on or dip preparation.
  • compositions made according to the invention will find the greatest application in sheep, they are also useful in treating cattle, deer, buffalo, cats, horses, dogs and goats. It will be appreciated that the parasiticide composition may be used to treat a variety of parasites which include but are not limited to lice parasites. In particular, the parasiticide composition is used to treat the lice parasite in the fleece of sheep.
  • a water washable parasiticide composition comprising: 0.2 - 10% w/v triflumuron; 0.05 - 5% w/v one or more emollients selected from the group consisting of lanolin acetate, cetyl acetate, lauric acid hexyl ester, caprylic/capric triglyceride, palmitic acid isopropyl ester, cetyl alcohol and mixtures thereof; 0.05 - 5% w/v one or more surfactants selected from the group consisting of C8- C10 alkylphenol ethoxylates, C9-C17 alcohol ethoxylates, C8-C20 alkyl amine ethoxylates, castor oil ethoxylates, lanolin alcohol ethoxylates, sorbitan fatty acid ester ethoxylates, sorbitan fatty acid esters and mixtures thereof; and 0.075- 5% 5% w/v one or more emollients selected
  • the parasiticide composition according to the firs aspect of the invention may be referred to as a "low residue composition", a “composition that has a low residue level”, a composition that results in a "low level of IGR and optionally SP residue” or a composition that will “reduce the residue loading”.
  • “low residue”, “low level of IGR and optionally SP residue” and “reduce the residue loading” is referring to the level of IGR and optionally SP, residing in the hide, fur, wool and/or consumable portions (e.g. meat, fat and/or milk) of the animal to which the parasiticide composition has been applied.
  • low residue means that the level of insect growth regulator (IGR) and optionally synthetic pyrethroid (SP) present in the hide, fur, wool or consumable portions of the animal, is in a concentration that is ⁇ ecognised as acceptable for human contact and/or consumption within a time period that is less than the withholding period for currently available IGR containing products as specified by the relevant authorities in each country, that is there is no need to treat the hide, fur, wool, and or consumable portions to reduce the levels of IGR or SP.
  • IGR insect growth regulator
  • SP optionally synthetic pyrethroid
  • the inventors have surprisingly found that when triflumuron is used as the IGR in a preferred embodiment of the first aspect of the invention, the level of triflumuron is below the Maximum Residue Level set by the Australian Pesticides and Veterinary Medicines Authority of 2mg kg in a period of time that is less than the 14 day withholding period currently set for available parasiticides containing triflumuron.
  • MRL Maximum Residue Limit
  • MRL values for some IGR's published by the Australian Pesticides and Veterinary Medicines Authority are given in Table 1 below.
  • the withholding period for milk is the minimum period of time that must elapse between the last treatment of an animal with a veterinary medicine and the next milking from which milk from that animal can be used for human consumption or supplied for processing.
  • the withholding period for meat is the minimum period of time that must elapse between the last treatment of an animal with a veterinary medicine and its slaughter for human consumption. In Australia and most other countries throughout the world, all veterinary medicines and chemicals intended for treatment of food-producing animals are required to have a withholding period stated on the label.
  • MRL Maximum Residue Limits
  • IGR's particularly IGR's selected from the group consisting of triflumuron, cyromazine, diflubenzuron, fluazuron and methoprene and mixtures thereof.
  • Residue and Safety Trials were carried out using the parasiticide composition according to a preferred embodiment of the first aspect of the invention as a pour-on composition.
  • This result is surprising given that the current parasiticide products on the market containing comparable amounts of triflumuron (ZAPP® Bayer) and (Epic® Jurox) specify that a 14 day withholding period is required before the treated animals can be slaughtered for human consumption, indicating that the residue level of triflumuron is well above the MRL one (1) day after application of the composition to the animal.
  • the level of IGR will advantageously meet the MRL almost immediately after application to the animal and accordingly will not be subject to the Meat Withholding Period required for livestock treated with the triflumuron parasiticide compositions known to the present inventors that are currently on the market.
  • preliminary results revealed that lice counts conducted 21 days after application of the composition of the invention according to Example 5 and Example 1 resulted in an average lice drop of 99.4% and 97.6 % respectively (see Table 9).
  • compositions of the invention containing lower concentrations of IGR are as effective as compositions containing higher concentrations of IGR in controlling lice on sheep.
  • the inventors have found that compositions containing 1.0 g/L Triflumuron (0.1% w/v) and 0.4 g L alpha-oypermethrin (0.04% w/v) (e.g see Example 7) control the lice counts over a 140 day period as effectively as compositions containing 25 gL Triflumuron (2.5% w/v) (e.g see Example 1).
  • the level of Triflumuron in the wool of a sheep was found to be 5.5 - 6.0 fold less (based on comparison of averages from each sample group) than the level of insecticide from a composition containing Triflumuron (2.5% w/v) according to Example 1. Accordingly, using a lower concentration of triflumuron in the composition of the invention i$ as effective as a composition of the invention containing higher concentrations of triflumuron and has resulted in reduced loading of IGR in the waste water from the effluent of a textile scouring plant.
  • the parasiticide composition of the present invention provides a composition that is efficacious against lice at low levels of active, is rainfast and reduces the residue loading in.the wool of a sheep being treated with such a composition.
  • rainfast will be understood to mean that the IGR has a higher tolerance to water when the dosed animal is exposed to rain or the animal is wet upon application, The IGR and SP are fully solubilised in the parasiticide composition of the present application and improves the tolerance of the IGR to water.
  • the inventors believe that this water tolerance reduces the amount of precipitated IGR around the point of application and allows the active to spread further around the body thereby improving it's efficacy. This improved efficacy allows the active concentration to be reduced, which in turn reduces the amount of residue on the animal.
  • the emollient plays a vital role in the parasiticide composition of the present invention by aiding solubilisation of the IGR and optionally SP and helping the IGR or IGR/SP combination to stay close to the skin a$ well as along the length of the wool staple.
  • the improvement in the solubility of the IGR or IGR SP combination has allowed for a prolonged release of the IGR or IGR/SP combination, thus allowing die amount of active required to be effective to be reduced.
  • the formulation of the present invention is lipophilic and accordmgly, the composition of the present invention has a tendency to solubilise well with the wool wax. Without being bound by theory, the present inventors believe that the composition of the present invention, being lipophilic, has a high tolerance to water and accordingly allows the active to move freely throughout an aqueous environment..
  • Example 1 The composition in Example 1 was prepared by dissolving the triflumuron in N- methylpyrrolidone and dipropyleneglycol monomethyl ether, followed by the addition of cetyl acetate, lanolin acetate and Polysorbate 80.
  • Example 2 The composition in Example 2 was prepared by dissolving the triflumuron in N- methylpyrrolidonc and dipropyleneglycol monomethyl ether, followed by the addition of Cetiol A and Myritol 318.
  • Example 3 The composition in Example 3 was prepared by dissolving the cyromazine in dipropyleneglycol monomethyl ether, followed by the addition of the emollient and fragrance. Dipropyleneglycol monoethyl ether was added to make up to volume
  • Example 4 The composition in Example 4 was prepared by dissolving the Diflubenzuron Glycol ether, followed by the addition of the emollient.
  • Example 5 The composition in Example 5 was prepared by dissolving the triflumuron and alpha-cypermethrin in glycol ether and part of the aromatic hydrocarbon, followed by the addition of the emollient, fragrance and the remainder of the solvent.
  • Example 6 The composition in Example 6 was prepared by dissolving the triflumuron and alphacypermethri ⁇ in N-methylpyrrolidonc and dipropyleneglycol monomethyl ether, followed by the addition of cetyl acetate, lanolin acetate and Polysorbate 80.
  • Example 7 The composition in Example 7 was prepared by dissolving the triflumuron and alphacypctmethrin in N-methylpyrrolidone and dipropyleneglycol monomethyl ether, followed by the addition of cetyl acetate, lanolin acetate and Polysorbate 80.
  • Example 8 The composition in Example 8 was prepared by dissolving the triflumuron in N- methylpyjTolidonc and dipropyleneglycol monomethyl ether, followed by the addition of cetyl acetate, lanolin acetate and Polysorbate 80.
  • an "effective amount of parasiticide composition” may be achieved using a dose volume that is calculated using (i) the weight of the animal or (ii) the surface area of the animal.
  • Table 3 provides dose volumes calculated on (i) the weight of the animal for a composition according to Example 1. It can be seen that for an animal weighing 10 kg and up to 95 kg, seven different dose volumes are required to effectively administer the composition to each ariimal.
  • the following dose volumes as shown in Table 4 are for a composition of the invention according to Example 5 and have been calculated based on the surface area of the animal rather than the body weight. For convenience of the end user, the surface area calculations were converted back to a weight range in kg. It can be seen that for an animal weighing ⁇ 20 kg and up to 104 kg, only four different dose volumes are required to effectively administer the composition to each animal. Based on the above, calculating the dose volume based on (ii) the surface area provides a more convenient dosage regime for the end user when the composition is required to be administered to a number of animals of varying weight. Table 4:
  • the residue level of triflumuron in the perirenal fat of the sheep was found to be approximately 0.2 mg kg, one (1) day after application of the composition to the sheep. This is about 8 times less than the MRL set by the Australian Pesticides and Veterinary Medicines Authority (A.PN.M.A.)
  • the maximum residue found was 0.454 which is approximately 4.5 times less that the MRL set by the A.PN.M.A.
  • Table 5 and 6 show the data from 0 -10 days and 10 - 66 days respectively. Table 5.
  • Contents of Triflumuron in Kidney, muscle, peri-renal and backfat from sheep treated with a composition according to Example 1 (2.5%w/v Triflumuron) 0 - 10 Days Slaughter.
  • compositions containing 1.0g/L Triflumuron (0.1% w/v) (according to Example 8), 1.0 g/L Triflumuron (0.1% w/v) and 0.4 g/L alpha-cypem ethrin (0.04% w/v) (according to Example 7) control the lice counts over a 140 day period as effectively as compositions according to the invention with higher concentrations of triflumuron, specifically, 25 g L triflumuron (2.5% w/v) according to Example 1 and 25 g/L Triflumuron (2.5% w/v) and 10 g/L (1.0% w/v). (according to Example 6).
  • the results shown below indicate that a 10 fold reduction in the amount of active dosed to the sheep is as effective in reducing the lice to a level of control over a period of 140 days.
  • Table 8 The results are shown in Table 8.
  • Table 9 shows the result on lice count 21 days after applying the composition of the invention according to Example 5 and Example 1 to horses. These preliminary results reveal that lice counts conducted 21 days after application resulted in an average lice drop of 99.4% and 97.6 % respectively. Table 9:

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EP04801110A 2003-12-04 2004-12-02 Verbesserte parasitizid-zusammensetzung Withdrawn EP1694362A4 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2003906726A AU2003906726A0 (en) 2003-12-04 Improved parasiticide composition
PCT/AU2004/001688 WO2005053746A1 (en) 2003-12-04 2004-12-02 Improved parasiticide composition

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EP1694362A4 true EP1694362A4 (de) 2008-09-03

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EP1924327A2 (de) * 2005-04-15 2008-05-28 Biomac Privatinstitut für medizinische und Zahnmedizinische Forschung, Entwicklung und Diagnostik GmbH Substanzen und pharmazeutische zusammensetzungen zur hemmung von glyoxalasen und ihre verwendung bei der bekämpfung von krebs
AU2006100580C4 (en) * 2006-07-12 2008-08-14 Jurox Pty Ltd Pesticide composition
NZ552096A (en) * 2006-12-15 2009-06-26 Merial Ltd Veterinary formulation
GB0804619D0 (en) * 2008-03-12 2008-04-16 Norbrook Lab Ltd A topical ectoparasiticide composition
GB2464449B (en) * 2008-09-05 2011-10-12 Norbrook Lab Ltd A topical ectoparasticide composition
BRPI1002174A2 (pt) * 2010-06-17 2012-03-13 Rotam Agrochem International Company Ltd Composição agroquímica, uso de um éter c2-c4 dialquileno glicol di-/mono-c1-c4 aquil, método para reduzir irritação ocular de formulações inseticidas líquidas, método de tratamento de praga em loco e uso da composição
BRPI1002288A2 (pt) * 2010-06-17 2012-03-13 Rotam Agrochem International Company Ltd Composição agroquímica, uso de um éter alquila di/mono c1-c4 dialquileno glicol c2-c4, método de preparação de uma formulação agroquímica de emulsão ew, método de tratamento de pragas em loco e uso da composição
CN105211091B (zh) * 2015-11-09 2017-11-21 山东省农业科学院植物保护研究所 一种防治二点委夜蛾的复配农药及方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082437A2 (de) * 1981-12-23 1983-06-29 A. Nattermann & Cie. GmbH Neue Pflanzenschutzmittelsuspensionskonzentrate
EP0331474A1 (de) * 1988-03-02 1989-09-06 The Wellcome Foundation Limited Sprühformulierungen
AU2002100152A4 (en) * 2002-02-28 2002-04-11 Jurox Pty Ltd Parasiticide composition
WO2002094221A1 (en) * 2001-05-18 2002-11-28 Jupitar Pty Ltd Emulsion and dispersion formulations and method
AU2003100144B4 (en) * 2003-02-28 2004-03-04 Jurox Pty Ltd Lousicide composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082437A2 (de) * 1981-12-23 1983-06-29 A. Nattermann & Cie. GmbH Neue Pflanzenschutzmittelsuspensionskonzentrate
EP0331474A1 (de) * 1988-03-02 1989-09-06 The Wellcome Foundation Limited Sprühformulierungen
WO2002094221A1 (en) * 2001-05-18 2002-11-28 Jupitar Pty Ltd Emulsion and dispersion formulations and method
AU2002100152A4 (en) * 2002-02-28 2002-04-11 Jurox Pty Ltd Parasiticide composition
AU2003100144B4 (en) * 2003-02-28 2004-03-04 Jurox Pty Ltd Lousicide composition

Non-Patent Citations (1)

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Title
See also references of WO2005053746A1 *

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