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EP1207851A1 - Formulations ectoparasiticides topiques organiques - Google Patents

Formulations ectoparasiticides topiques organiques

Info

Publication number
EP1207851A1
EP1207851A1 EP00948749A EP00948749A EP1207851A1 EP 1207851 A1 EP1207851 A1 EP 1207851A1 EP 00948749 A EP00948749 A EP 00948749A EP 00948749 A EP00948749 A EP 00948749A EP 1207851 A1 EP1207851 A1 EP 1207851A1
Authority
EP
European Patent Office
Prior art keywords
formulation
formulations
weight percent
spinosad
animal
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Withdrawn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
EP00948749A
Other languages
German (de)
English (en)
Inventor
James Web Kassebaum
Paul Thomas Pugh
William Webster Thompson
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of EP1207851A1 publication Critical patent/EP1207851A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A61K9/0017—Non-human animal skin, e.g. pour-on, spot-on
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • This invention relates to topical organic ectoparasiticidal formulations.
  • Ectoparasites such as fleas, blowflies, lice, ticks and mites can seriously affect productivity in the domesticated animal industries. Further, such parasites cause disease and discomfort for pets and other companion animals.
  • Ectoparasites are often controlled by topically applying an insecticide or mixture of insecticides onto the animal.
  • Topical ectoparasite control agents are usually applied in liquid formulations. The formulations can be applied by spot-on application, plunge or spray dipping, jetting with a hand held spray or in a race, or as a back- line spray or pour-on.
  • a particular problem with topical formulations is poor migration from the site of application.
  • treatment for ectoparasites is commonly carried out in the early season within 24 hours after shearing, or, less frequently, later in the season when the wool is longer.
  • the topical formulation is applied along the dorsal midline or back- line of the animal, the insecticide component of currently available commercial formulations migrates very poorly from the application site. Typically less than 10% of the applied insecticide diffuses away from the application site within the first 10 days. Thus, extensive areas of the animal's skin and/or hair may receive sublethal concentrations of the insecticide. These areas remain susceptible to damaging invasion by ectoparasites.
  • Solvent-based formulations have received attention in recent times in the search for greater insecticide mobility that would allow the same insecticidal effect to be achieved with less insecticide in the formulations. Up to the present, there has been little success in identifying a solvent that materially enhances the spread of insecticides that are applied using a spot-on or pour-on method.
  • This invention provides insecticidal formulations that can be applied topically to animals and that have the advantage of permitting the active ingredient to spread over the surface of the skin and/or hair of the treated animal, thereby providing more extensive coverage of the insecticide. These formulations, therefore, provide greater inhibition or eradication of ectoparasites with smaller amounts of insecticide.
  • the topical ectoparasiticidal formulations of this invention comprise an ectoparasiticide, a spreading agent and optionally a miscibilizing agent. More specifically, the invention relates to a topical ectoparasiticidal formulation comprising from about 0.1 to about 25 weight percent of an ectoparasiticide, from about 25 to about 99.9 weight percent of a (C 3 -C 6 ) branched alkyl (C 10 -C 20 ) alkanoate spreading agent, and optionally up to about 70 weight percent of a miscibilizing agent compatible with organic solvent systems.
  • An exemplary topical ectoparasiticidal formulation of this invention is one wherein the ectoparasiticide is a spinosyn, or a physiologically acceptable derivative or salt thereof.
  • This invention also encompasses a method of controlling an ectoparasite infestation on a small ruminant or companion animal, comprising topically applying to the hair and/or skin of the animal a formulation comprising from about 0.1 to about 25 weight percent of a spinosyn, or a physiologically acceptable derivative or salt thereof, from about 25 to 99.9 weight percent isopropyl myristate, and from 0 to about 70 weight percent of a miscibilizing agent compatible with organic solvent systems.
  • the invention also relates to an article of manufacture, comprising packaging material and a topical formulation for controlling an ectoparasite infestation on a small ruminant or companion animal contained within said packaging material, wherein said formulation comprises a topical unit dose of a formulation comprising 0.1 to about 25 weight percent of an ectoparasiticide, from about 25 to about 99.9 weight percent of a (C 3 -C 6 ) branched alkyl (C 10 -C 20 ) alkanoate spreading agent, and optionally up to about 70 weight percent of a miscibilizing agent compatible with organic solvent systems; and, wherein said packaging material comprises a label or package insert with instructions for topically administering the dose to the animal.
  • This article of manufacture or kit is particularly appropriate when the companion animal is a dog or a cat.
  • the timing of administering the doses will generally be every 30 days.
  • Each kit typically contains a sufficient number of doses to control the ectoparasite infestation for a period of several months.
  • This invention further provides a topical formulation for controlling an ectoparasite infestation on a small ruminant or companion animal comprising a spinosyn, or a derivative or salt thereof, and a spreading agent substantially as hereinbefore described with references to any one of the Examples.
  • small ruminant animals are a sheep, a goat or a camellid.
  • controlling refers to either ameliorating or eliminating a current infestation or preventing an infestation in a susceptible host.
  • insecticidal agents are useful in the formulations of this invention. Indeed, any ectoparasiticidal compound that is soluble in a (C 3 -C 6 ) branched alkyl (C 10 -C 20 ) alkanoate vehicle and is useful for topical application can be incorporated as the insecticidal component of these formulations.
  • the insecticidal agent is active against a broad spectrum of pest species, including acaricides, antiparasitic agents, insect growth regulators and compounds that inhibit or kill flies, flying pests and other "temporary" pests that only alight momentarily on domesticated animals.
  • TEPP tetraethyl pyrophosphate
  • mevinphos disulfoton
  • azinphosmethyl parathion
  • methylparathion chlorfenvinphos
  • cichlorvos diazinon, dimethoate, trichlorfon, chlorothion, malathion, ronnel, abate, baygon, carbaryl, mobam, temik, zectran, methoxychlor, aldrin, dieldrin, endrin, heptachlor, chlordane, lindane, mirex, nicotine, rotenoids, pyrethrums, spinosyns and synthetic pyrethroids, including cypermethrin.
  • Preferred insecticides useful in these formulations are spinosyns or a pyrethroid such as cypermethrin.
  • Spinosyns are especially preferred.
  • the spinosyns also known as A83453 factors
  • the spinosyns were also known to have some ectoparasiticidal activity, i.e., they had in vitro activity against mosquito larvae, black blowfly larvae and adult stable flies, which are members of the insect order Diptera, and transient systemic activity against larval blowfly and adult stable fly in guinea pigs and sheep.
  • the spinosyns were administered in aqueous polyvinylpyrrolidone or in polyethylene glycol (see U.S. Patent No. 5,571,901, col. 26-32).
  • the spinosyns are naturally-derived macrolides produced by fermentation of Saccharopolyspora spinosa.
  • spinosyn A and spinosyn D are the two spinosyns that are most active as insecticides.
  • An agricultural product comprised mainly of these two spinosyns is available commercially under the name "spinosad”.
  • Spinosyn A was the first spinosyn isolated and identified from the fermentation broth of Saccharopolyspora spinosa. Subsequent examination of the fermentation broth revealed that S. spinosa produced a number of spinosyns that have been called spinosyns A to H and J. Additional spinosyns, denominated K to W, have been identified from various strains of S. spinosa.
  • the various spinosyns are characterized by differences in the substitution patterns on the amino group of the forosamine, at selected sites on the tetracyclic ring system and on the 2N,3N,4N-(tri- O-methyl)rhamnose group.
  • Boeck et al. described spinosyns A-H and J (which they called A83543 factors A, B, C, D, E, F, G, H and J), and salts thereof, in U.S. Patent Nos. 5,362,634 (issued Nov. 8, 1994); 5,496,932 (issued March 5, 1996); and 5,571,901 (issued Nov. 5, 1996).
  • Mynderse et al. described spinosyns L-N (which they called A83543 factors L, M and N), their N-dimethyl derivatives, and salts thereof, in U.S. Patent No. 5,202,242 (issued Apr. 13, 1993); and Turner et al.
  • spinosyns Q-T which they called A83543 factors Q, R, S and T
  • their N-dimethyl derivatives and salts thereof
  • U.S. Patent Nos. 5,591,606 issued January 7, 1997) and 5,631,155 (issued May 29, 1997).
  • Spinosyns K, O, P, U, V, W and Y are described, for example, by Carl V. DeAmicis, James E. Dripps, Chris J. Hatton and Laura I. Karr in American Chemical Society's Symposium Series: Phytochemicals for Pest Control, Chapter 11, "Physical and Biological Properties of Spinosyns: Novel Macrolide Pest- Control Agents from Fermentation", pages 146-154 (1997).
  • the spinosyns can be isolated in the form of salts that are also useful in the formulations of this invention.
  • the salts are prepared using standard procedures for salt preparation. For example, spinosyn A can be neutralized with an appropriate acid to form an acid addition salt.
  • Suitable acid addition salts include salts formed by reaction with either an organic or inorganic acid, for example, sulfuric, hydrochloric, phosphoric, acetic, succinic, citric, lactic, maleic, fumaric, cholic, pamoic, mucic, glutamic, camphoric, glutaric, glycolic, phthalic, tartaric, formic, lauric, stearic, salicylic, methanesulfonic, benzenesulfonic, sorbic, picric, benzoic, cinnamic and like acids.
  • an organic or inorganic acid for example, sulfuric, hydrochloric, phosphoric, acetic, succinic, citric, lactic, maleic, fumaric, cholic, pamoic, mucic, glutamic, camphoric, glutaric, glycolic, phthalic, tartaric, formic, lauric, stearic, salicylic, methanesulfonic, benzenes
  • a “spinosyn or a derivative thereof as used herein refers to an individual spinosyn factor (spinosyn A, B, C, D, E, F, G, H, J, K, L, M, N, O, P, Q, R, S, T, U, V, W or Y), an N-dimethyl derivative of one or more spinosyn factor, or a combination thereof.
  • the term “spinosyn component” as used means an individual spinosyn or a physiologically acceptable derivative or salt thereof, or a combination thereof.
  • spinosad refers to a mixture of spinosyns comprised mainly of spinosyns A and D.
  • spinosyns are known to have excellent human and animal safety and toxicological profiles. Because of their low toxicity to animals and humans, spinosyns are considered to be environment-friendly, "green” insecticides. It is desirable to formulate spinosyns to maintain this "green” profile. Spinosyns have recently been found to be useful in the eradication or control of ectoparasites on sheep and companion animals. Thus, formulations of spinosyns with low toxicity and increased stability are potentially valuable in combating ectoparasites and the diseases such pests often carry.
  • the present formulations further comprise a (C 3 -C 6 ) branched alkyl (C 10 -C 20 ) alkanoate.
  • This component is an organic solvent that acts as a spreading agent. Spreading agents increase the spreading of, and aid in substantially equalizing the distribution of, the active ingredient over the hair and/or skin surface area of the animal over time.
  • the spreading agent solvent system should be safe, non-toxic, environment-friendly and non-flammable.
  • the branched alkyl portion of the (C 3 -C 6 ) branched alkyl (C 10 -C 20 ) alkanoate includes all branched chain isomers of C 3 -C 6 alkyl groups. Examples are isopropyl, isobutyl, isopentyl, and isohexyl.
  • the (C ⁇ n -C 20 ) alkanoate moiety includes all C ⁇ o-C 2 o fatty alkanoate groups, including but not limited to, decanoate (C 10 ), hendecanoate (C u ), dodecanoate (C I2 ), tridecanoate (C 13 ), tetradecanoate (C 14 ), pentadecanoate (C ⁇ 5 ), hexadecarioate (C 16 ), heptadecanoate (C 17 ), octadecanoate (C 18 ), and eicosanoate (C 20 ).
  • decanoate C 10
  • hendecanoate C u
  • dodecanoate C I2
  • tridecanoate C 13
  • tetradecanoate C 14
  • pentadecanoate C ⁇ 5
  • hexadecarioate C 16
  • heptadecanoate C 17
  • the spreading agent is a (C 3 -C 6 ) branched alkyl (C 12 -C 16 ) alkanoate. Of these solvents, C 3 - branched alkyl-C 14 alkanoates are especially useful.
  • a preferred spreading agent is isopropyl myristate (IPM).
  • the formulations can optionally contain a miscibilizing agent.
  • the miscibilizing agent aids in solubilizing the active ingredient and must be compatible with organic solvent systems.
  • compatible with organic solvent systems means that the miscibilizing agent does not form more than one phase when mixed with the (C 3 -C 6 ) branched alkyl (C 10 -C 2 o) alkanoate component.
  • Suitable miscibilizing agents for use in these formulations generally are (C ! -C 30 ) organic acids.
  • organic acids are straight-chain saturated fatty acids, but they can also be low molecular weight organic acids such as formic acid, acetic acid, propionic acid and benzoic acid.
  • miscibilizing agent will vary depending on the insecticide in the formulation.
  • suitable miscibilizing agents are formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, benzoic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, oleic, arachidic acid, behenic acid, lignoceric acid, cerotic acid, montanic acid, triacontanoic acid, psyllic acid, and ceroplastic acid.
  • Other useful miscibilizing agents are (C,-C 30 ) alkyl sulfuric acids, (C ⁇ -C 3 o) alkyl phosphoric acids, and (C,-C 30 ) alkyl sulfonic acid, and ceroplastic acid.
  • oleic acid is a particularly useful miscibilizing agent because it aids in solubilizing the spinosyn (thus allowing for the formation of solvent solutions containing relatively high concentrations of active ingredient), and it is compatible with the isopropyl myristate component.
  • miscibilizing agents in the formulations of this invention.
  • a miscibilizing compound useful for these formulations 1) is compatible with the selected organic solvent component, and 2) solubilizes the active ingredient without substantially altering the spreading properties of the formulation.
  • VvTien insecticide is a spinosyn and the spinosyn component is spinosyn D or spinosad (i.e., a mixture of spinosyns A and D), it is especially important that the miscibilizing agent is able to solubilize the spinosyn D sufficiently.
  • factor D is generally the factor that causes solubility problems when preparing spinosad-containing formulations.
  • the present formulations can also contain other optional ingredients, such as: antioxidants, UN-absorbing compounds or photostabilizers, viscosity- modifying agents, antimicrobial agents, dyes, perfumes, deodorants and physiologically or dermatologically acceptable carriers, diluents, excipients or adjuvants. Such agents are known in the art.
  • one or more antioxidants can be added to the formulations in an amount effective to retard oxidation of the formulation components and the ensuing degradative effects.
  • Potentially useful antioxidants include primary antioxidants that are radical scavengers, such as hindered phenolics and secondary amines, and secondary antioxidants, such as phosphites and thioesters that function as peroxide decomposers.
  • Preferred antioxidants for use in these formulations are blends of primary and secondary antioxidants, including particularly blends of phenolic and phosphite antioxidant compositions.
  • antioxidants products designed for polymer stabilization including antioxidant formulations comprising synergistic combinations of primary and secondary antioxidants.
  • examples of commercially available antioxidants useful in the formulations of this invention include the Irganox® antioxidants available from Ciba Geigy, Vanox® antioxidants from R.T. Vanderbilt, and the Naugard® antioxidants available from Uniroyal Chemicals.
  • the formulations of this invention can be prepared by blending the components with adequate mixing or stirring.
  • a useful spinosad formulation is one having a final concentration of 2 mg of spinosad per mL.
  • One such formulation is prepared to contain 99.1 weight percent IPM, 0.6 weight percent oleic acid, and 0.3 weight percent spinosad technical (89% active ingredient).
  • This formulation is made by adding the appropriate amount of spinosad to the IPM solvent with mixing or stirring, blending the oleic acid into the IPM/spinosad mixture, and continuing the mixing or stirring until the spinosad has completely solubilized to form the final formulation product.
  • An optional additional step is to filter the final formulation to remove any impurities or extraneous materials.
  • the formulations of this invention are applied to the animal topically.
  • Topical control protocols include spot-on or pour-on treatments wherein the formulation is placed directly onto a discreet skin and/or hair surface area of the animal and allowed to spread over the remainder of the animal's skin or hair surface area.
  • spot-on or pour-on protocols involve initially placing the formulation on the dorsal midline (i.e., the head, neck, shoulders or back) of the animal.
  • Placement typically occurs on a dorsal midline surface area that constitutes less than 10% of the animal's entire surface area.
  • a typical pour-on treatment protocol involves applying about 4 to about 50 mL of a liquid ectoparasiticidal formulation in a narrow strip along the backline of an animal, from the withers to the tail or rump.
  • the ectoparasiticidal active ingredient For spot-on or pour-on treatment to control ectoparasites, such as lice, which are present over the whole surface of an animal, the ectoparasiticidal active ingredient must spread from the narrow strip at the backline to cover the entire surface of the animal.
  • the present formulations have this advantageous spreading effect. Of course, they can be applied to areas of skin that constitute greater than 10% of the surface area of the animal, but such applications limit the advantage offered by these formulations. Another advantage of these formulations is that they offer extended ectoparasiticidal coverage and need not be applied more than weekly or biweekly at most.
  • solvent systems that are capable of solubilizing at least 1% spinosad by weight percent were screened for hair wetting by applying about 1 mL of the solvent system (solvents were screened without active ingredient), dropwise, to a tanned rabbit pelt that was at an angle of about 45 ° . Solvent systems that wet the rabbit hair and did not run off before wetting the hair were considered to pass the screen. Table I describes the ability of selected organic solvents to wet the rabbit hair.
  • isopropyl myristate gave the greatest spread of zeta-cypermethrin and the wool grease fraction FI provided the least spreading.
  • the vehicle was the FI wool grease fraction, only the 2-cm meridian showed increased concentration of zeta-cypermethrin over time after initial application.
  • the quantity of zeta- cypermethrin measured at all meridians increased with time following administration.
  • Octyl stearate and glyceryl tricaprylate/caprate gave modest spread, but not as great as the spread provided by the IPM formulations. Tissue residues were similar amongst formulations except the glyceryl tricaprylate/caprate formulation appeared to cause the highest residue levels.
  • FI was a comparatively poor spreading agent
  • octyl stearate and glyceryl tricaprylate/caprate provided better spreading properties
  • isopropyl myristate gave the best spread of zeta- cypermethrin.
  • IPM Formulation 99.12 % IPM 0.61 % oleic acid 0.27 % spinosad technical (89% active)
  • OP/IPM Formulation 79.78% octyl palmitate (OP) 19.95% IPM
  • TPM tripropylene glycol methyl ether
  • LWG liquid wool grease
  • Example 5 Spinosad IPM/acetic acid Formulation 5.65%o spinosad (88.5% active) 3% acetic acid 91.35% IPM
  • Example 6 Spinosad IPM/octanoic acid Formulation 5.65%o spinosad (88.5% active) 7.5%o octanoic acid
  • the formulations of Examples 5-10 can be prepared by weighing the spinosad into a suitable container, adding the IPM and stirring to create a slurry, and then adding the final component and stirring until a clear solution is achieved.
  • the zeta-cypermethrin is an oily liquid that equires gentle heating (approximately 4 ⁇ -50°C) to allow for proper mixing into the organic solvent phase. No separation of phases is evident upon cooling.

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  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Zoology (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

La présente invention concerne des formulations ectoparasiticides topiques comprenant un ectoparasiticide, de préférence une pyréthroïde ou une spinosyne, un agent d'étalement qui est un alkanoate (C10-C20) alkyle ramifié (C3-C6), de préférence un isopropyl myristate, et éventuellement un agent de miscibilité compatible avec des systèmes de solvant organique. Cette invention concerne également des procédés permettant de contrôler l'infestation ectoparasitaire chez certains animaux, comprenant l'application topique desdites formulations sur l'animal.
EP00948749A 1999-08-12 2000-07-26 Formulations ectoparasiticides topiques organiques Withdrawn EP1207851A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US14850899P 1999-08-12 1999-08-12
US148508P 1999-08-12
PCT/US2000/019549 WO2001012156A1 (fr) 1999-08-12 2000-07-26 Formulations ectoparasiticides topiques organiques

Publications (1)

Publication Number Publication Date
EP1207851A1 true EP1207851A1 (fr) 2002-05-29

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ID=22526069

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00948749A Withdrawn EP1207851A1 (fr) 1999-08-12 2000-07-26 Formulations ectoparasiticides topiques organiques

Country Status (17)

Country Link
EP (1) EP1207851A1 (fr)
JP (1) JP2003520779A (fr)
AR (1) AR025234A1 (fr)
AU (1) AU770542B2 (fr)
BR (1) BR0013245A (fr)
CA (1) CA2380643A1 (fr)
CO (1) CO5221105A1 (fr)
HU (1) HUP0202823A2 (fr)
IL (2) IL147829A0 (fr)
MX (1) MXPA02001502A (fr)
MY (1) MY128816A (fr)
NO (1) NO20020685L (fr)
NZ (1) NZ516781A (fr)
PE (1) PE20010359A1 (fr)
SV (1) SV2002000143A (fr)
TW (1) TWI236376B (fr)
WO (1) WO2001012156A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6927210B1 (en) 1999-08-12 2005-08-09 Eli Lilly And Company Ectoparasiticidal aqueous suspension formulations of spinosyns
HUP0202825A2 (en) 1999-08-12 2003-03-28 Lilly Co Eli Oral treatment of companion animals with ectoparasiticidal spinosyns
US6933318B1 (en) 1999-08-12 2005-08-23 Eli Lilly And Company Topical organic ectoparasiticidal formulations
AUPQ441699A0 (en) * 1999-12-02 2000-01-06 Eli Lilly And Company Pour-on formulations
US6727228B2 (en) 2001-04-25 2004-04-27 Johnson & Johnson Consumer Companies, Inc. Pediculicidal and ovacidal treatment compositions and methods for killing head lice and their eggs
DK2347654T3 (en) 2001-09-17 2019-04-23 Elanco Us Inc Formulation for the control of lice or ticks in cattle
US6663876B2 (en) * 2002-04-29 2003-12-16 Piedmont Pharmaceuticals, Llc Methods and compositions for treating ectoparasite infestation
US8007820B2 (en) * 2005-09-16 2011-08-30 W. Neudorff Gmbh Kg Wide spectrum insecticide and miticide composition
AR061123A1 (es) 2006-05-25 2008-08-06 Dow Agrosciences Llc Fumigantes de espinosina
WO2007144786A2 (en) * 2006-05-26 2007-12-21 Entarco Sa The vapor-phase application of spinosyn for the control of pests, and formulations and products utilizing the same
EP2248422A1 (fr) * 2009-05-08 2010-11-10 Novartis AG Compositions pour lutter contre les ectoparasites
TWI510189B (zh) * 2009-06-19 2015-12-01 Lilly Co Eli 殺外寄生蟲之方法及調配物
WO2010150100A1 (fr) * 2009-06-24 2010-12-29 Entarco Sa Utilisation de spinosynes et de compositions à base de spinosyne pour lutter contre des affections provoquées par des protozoaires, contes des infections virales et contre le cancer
US8921327B2 (en) 2012-11-14 2014-12-30 Eli Lilly And Company Ectoparasiticidal methods and formulations
AU2019348204B2 (en) * 2018-09-27 2025-06-26 0903608 B.C. Ltd. Synergistic pesticidal compositions and methods for delivery of insecticidal active ingredients
EP3855910A4 (fr) * 2018-09-27 2022-06-29 0903608 B.C. Ltd. Compositions pesticides synergiques et procédés d'apport d'agents actifs

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DE3125897A1 (de) * 1981-07-01 1983-02-10 Bayer Ag, 5090 Leverkusen Ektoparasitizide sprueh-formulierungen
DE3317823A1 (de) * 1983-05-17 1984-11-22 Bayer Ag, 5090 Leverkusen Schaedlingsbekaempfungsmittel
CO5210925A1 (es) * 1998-11-17 2002-10-30 Novartis Ag Derivados de diamino nitroguanidina tetrasustituidos

Non-Patent Citations (2)

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Also Published As

Publication number Publication date
AR025234A1 (es) 2002-11-13
PE20010359A1 (es) 2001-04-03
CO5221105A1 (es) 2002-11-28
BR0013245A (pt) 2002-04-16
SV2002000143A (es) 2002-02-05
NZ516781A (en) 2003-03-28
JP2003520779A (ja) 2003-07-08
IL147829A0 (en) 2002-08-14
CA2380643A1 (fr) 2001-02-22
HUP0202823A2 (en) 2003-03-28
IL147829A (en) 2006-08-20
WO2001012156A1 (fr) 2001-02-22
MXPA02001502A (es) 2002-07-02
AU6220600A (en) 2001-03-13
NO20020685D0 (no) 2002-02-11
AU770542B2 (en) 2004-02-26
TWI236376B (en) 2005-07-21
MY128816A (en) 2007-02-28
NO20020685L (no) 2002-04-09

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