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WO1986007525A1 - Compositions parasiticides a base de pyrethroide - Google Patents

Compositions parasiticides a base de pyrethroide Download PDF

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Publication number
WO1986007525A1
WO1986007525A1 PCT/GB1986/000356 GB8600356W WO8607525A1 WO 1986007525 A1 WO1986007525 A1 WO 1986007525A1 GB 8600356 W GB8600356 W GB 8600356W WO 8607525 A1 WO8607525 A1 WO 8607525A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
water
pyrethroid
levamisole
compositions
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB1986/000356
Other languages
English (en)
Inventor
Andrew Rennie Galbraith
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.)
Robert Young & Co Ltd
Original Assignee
Robert Young & Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Robert Young & Co Ltd filed Critical Robert Young & Co Ltd
Publication of WO1986007525A1 publication Critical patent/WO1986007525A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A01N25/00—Biocides, 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
    • A01N25/02—Biocides, 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 containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles

Definitions

  • Pyrethroid-containing Parasticidal Compositions This invention concerns pyrethroid-containing compositions for controlling ectoparasties such as lice, keds, mites, ticks, fleas and nuisance fly and endoparasites such as helminths including gut and lungworms which may infest non-human animals. More specifically the invention is concerned with aqueous compositions containing at least one synthetic (light-stable) pyrethroid insecticide and at least one anthelmintic agent.
  • compositions may be provided in a form suitable for subsequent pour-on or spot-on application to the skin or fleece of a non-human animal according to well known techniques. They may, most conveniently, comprise solutions of the active ingredients.
  • compositions are provided which can confer dual control, rendering separate treatments for ecto- and endo-parasites unnecessary.
  • Tetramisole, 2,3,5,6 -tetrahydro-6-phenylimidazo (2,1-b) thiazole and its (L-) laevo isomer levamisole are known to be effective anthelmintic agents.
  • Tetramisole is a racemic mixture of the D- and L- isomers and the activity against helminths has been shown to be derived mainly or almost entirely from levamisole. Tetramisole and levamisole are described in GB-A-1 043489.
  • GB-A-1464 552 is concerned with a method of using tetramisole and/or levamisole by application to the skin of an animal.
  • the salts should be avoided due to reduced efficacy and water is stated to be an ineffective carrier for effecting passage of the active ingredient through the skin, a pre-requisite to helmintic control.
  • Anthelmintic compositions based on conventional organic solvents have caused skin irritation or damage in the treated animal.
  • GB-A-2095107 discloses anthelmintic compositions having reduced skin irritation problems.
  • Synthetic pyrethroids as disclosed in GB-A-1413491 are known to be powerful insecticides suitable for ectoparasite control on non- human animals.
  • X 5 is - H or halo; R 1 is H or cyano; and
  • R 2 is halogen-substituted phenyl.
  • a parasiticide! composition suitable for pour-on application to a non-human animal which comprises: (i) at least one salt of tetramisole and/or levamisole,
  • composition may include (v) a minor proportion (less than
  • compositions for controlling endo- and ectoparasites in a non-human animal and methods of controlling such parasites by use of the compositions.
  • the term controlling is used to mean interfering with the development and/or reproduction of the parasite(s).
  • the compositions are solutions and they may be prepared by admixture of the relevant ingredients with (v), when present, being added to (iv) before or after addition of (iii).
  • salt(s) of levamisole such as acid addition salt(s).
  • levamisole hydrochloride levamisole phosphate and levamisole citrate and levamisole oleate may be mentioned.
  • the most preferred salt is levamisole hydrochloride.
  • pyrethroids one or more of permethrin, cypermethrin, cyholothrin or decamethrin may be employed. It is more preferred to use permethrin and most preferred to use permethrin in high-cis form.
  • Permethrin contains cis- and trans-isomers and it has been found that the cis-isomer is the more effective in controlling lice, keds, mites, fleas or the like, but particularly nuisance fly on cattle. Water may be present (by weight per unit volume of solution) in an amount of 5 - 30%, preferably 10 - 25%, more preferably 12 - 20% w/v.
  • organic water-miscible cosolvent examples include one or more of the following, separately or as a mixture of two or more thereof: alkanols, alkoxyalkanols, alkoxy-alkoxyalkanols, dipolar aprotic solvents such as dimethylsulphoxide (DMSO) or dimethylformamide (BMP) and the like. It is preferred to use one or more alcohols of the formula ( V ) :
  • ethanol also known as diethylene glycol monobutyl ether (DGBE), which we have found well tolerated by animal skins or hides.
  • Component (iv) may comprise at least 50% by weight, preferably 80% or more of DGBE.
  • the said solvent may itself be a mixture of solvents such as the commercial Solvent comprised almost entirely of aromatic hydrocarbon fractions b.p.186-205oC sold as Shellsol AB. This commercial solvent is preferred and comprises 35% C 9 -fraction, 49%C 10 -fraction, 9% C 11 -fraction and 7% napthalene and methylnaphalene.
  • the inclusion of water-immiscible solvent, such as C 9 - or higher aromatic hydrocarbon(s) may enhance skin penetration of the salt(s) (i) whilst retaining the components in solution, avoiding precipitation.
  • Component (v), when present, may be in a proportion of (by weight per unit volume of composition) 1 - 30%, preferably 5 - 30%, more preferably in the range 10 - 25% w/v of the carrier system.
  • compositions contain levamisole hydrochloride (and/or phosphate) high-cis permethrin, 2-(2-butoxyethoxy) ethanol, water with or without aromatic hydrocarbons.
  • compositions containing anthelmintically effective amount of (i) and insecticidally effective amount of (ii) according to the invention may retain the salt(s) in solution, and improve penetration of the anthelmintic salt into the animal's circulatory system through the skin barrier.
  • the carrier system may be at least as acceptable as use of DGBE alone in the sense that skin irritation in the present compositions may be no worse than and possibly better than pure DGBE solvent.
  • the following parasiticidal pour-on composition (solution) was prepared: levamisole hydrochloride 11.8 g high-cis permethrin 4.0 g water 15.0 g
  • Example 4 The following parasiticidal composition (solution) was prepared and effectively used to control helminths and sheep lice : levamisole hydrochloride 8.0 g cypermethrin 4.0 g
  • compositions were prepared and used as a pour-on for cattle : (A) (B) levamisole hydrochloride 11.8 g 23.6 g water 20. g 25. g
  • the pour-on compositions of examples 1 to 3 inclusive were found effective in controlling cattle nuisance fly and helminths.
  • the pour-on composition of Example 4 was found effective in controlling helminths in and lice on sheep.
  • the pour-on compositions of comparative Examples 5 (A) and 5 (B) were not found effective in controlling helminths in cattle despite the presence of a levamisole salt. In the absence of a pyrethroid the effect against ectoparasites was not monitored. In all of the tests no significant skin irritation or damage to the animal skin, fleece or hide was observed.
  • Example 1 to 3 showed significant improvement in anthelmintic activity whilst Example 4 was not compared.
  • the levamisole salt component penetrates cattle skin, in in vitro testing equipment, at a rate comparable to a commercial levamisole free base product consisting of 20% levamisole base in solvent DGBE.
  • Comparative formulations of Example 5 (A) and 5 (B) demonstrated little, if any, anthelmintic activity.
  • the pyrethroid component thus appears to synergise the activity and/or penetration of the levamisole salt.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Chemical & Material Sciences (AREA)
  • Plant Pathology (AREA)
  • Toxicology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Les compositions à appliquer localement pour lutter simultanément contre les ecto- et endo-parasites sur p. e. les ovins et les bovins, comprennent: (i) du sel de lévamisole et/ou de tétramisole, (ii) au moins un pyrétroïde, dans un système véhicule comprenant (iii) de l'eau, (iv) au moins un co-solvant organique miscible dans l'eau et éventuellement (v) au moins un solvant organique non miscible dans l'eau. La présence de (ii) semble améliorer de manière synergique l'action de (i) et la sélection de (iv) et de (v) permet de réduire au minimum les lésions ou les irritations thermiques. (i) doit être présent dans une quantité efficace sur le plan anthelmintique et (ii) dans une quantité efficace sur le plan insecticide.
PCT/GB1986/000356 1985-06-19 1986-06-19 Compositions parasiticides a base de pyrethroide Ceased WO1986007525A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB858515459A GB8515459D0 (en) 1985-06-19 1985-06-19 Parasitical compositions
GB8515459 1985-06-19

Publications (1)

Publication Number Publication Date
WO1986007525A1 true WO1986007525A1 (fr) 1986-12-31

Family

ID=10580948

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1986/000356 Ceased WO1986007525A1 (fr) 1985-06-19 1986-06-19 Compositions parasiticides a base de pyrethroide

Country Status (3)

Country Link
EP (1) EP0259340A1 (fr)
GB (2) GB8515459D0 (fr)
WO (1) WO1986007525A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0354761A3 (fr) * 1988-08-09 1991-05-08 CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. Compositions vétérinaires pour emploi contre les endoparasites et leur procédé de préparation
WO1992003047A1 (fr) * 1988-03-02 1992-03-05 Roussel-Uclaf Formulations pesticides
US5194264A (en) * 1989-03-13 1993-03-16 Scientific Chemicals (Proprietary) Limited Pesticidal formulation
EP0537447A1 (fr) * 1991-10-09 1993-04-21 DESOWAG GmbH Agent aqueux pour la protection du bois
EP0665011A1 (fr) * 1993-12-27 1995-08-02 Mitsui Toatsu Chemicals, Incorporated Parasiticide contre des endoparasites contenant un composé de type pyréthroide
WO2000047048A1 (fr) * 1999-02-08 2000-08-17 Virbac (Australia) Pty. Limited Traitement a pesticides
EP1182931A4 (fr) * 1999-06-04 2003-01-29 Nufarm Ltd Compositions biocides stables
EP1414304A1 (fr) 2001-07-25 2004-05-06 Syngenta Limited Melange insecticide contenant de la gamma-cyhalothrine
CN102771499A (zh) * 2012-07-09 2012-11-14 启东市中勇机电工具有限公司 无毒灭蝇剂

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2861076B2 (ja) * 1988-08-05 1999-02-24 住友化学工業株式会社 殺虫性水性液剤

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB640549A (en) * 1942-05-30 1950-07-19 Stanco Inc Method of preparing highly efficient insecticides for direct application to the skin of man and animals
GB2109236A (en) * 1981-10-19 1983-06-02 Wellcome Australia Aqueous pour-on formulation
GB2117638A (en) * 1982-03-16 1983-10-19 Wellcome Australia Pour-on formulation
WO1984000095A1 (fr) * 1982-07-02 1984-01-19 Young Robert Co Ltd Formules parasiticides
US4439439A (en) * 1981-03-24 1984-03-27 Janssen Pharmaceutica N.V. Non-irritating tetramisole- or levamisole pour-on conpositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB640549A (en) * 1942-05-30 1950-07-19 Stanco Inc Method of preparing highly efficient insecticides for direct application to the skin of man and animals
US4439439A (en) * 1981-03-24 1984-03-27 Janssen Pharmaceutica N.V. Non-irritating tetramisole- or levamisole pour-on conpositions
GB2109236A (en) * 1981-10-19 1983-06-02 Wellcome Australia Aqueous pour-on formulation
GB2117638A (en) * 1982-03-16 1983-10-19 Wellcome Australia Pour-on formulation
WO1984000095A1 (fr) * 1982-07-02 1984-01-19 Young Robert Co Ltd Formules parasiticides

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992003047A1 (fr) * 1988-03-02 1992-03-05 Roussel-Uclaf Formulations pesticides
EP0354761A3 (fr) * 1988-08-09 1991-05-08 CHINOIN Gyogyszer és Vegyészeti Termékek Gyára RT. Compositions vétérinaires pour emploi contre les endoparasites et leur procédé de préparation
AU629560B2 (en) * 1988-08-09 1992-10-08 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Veterinary composition against endoparasites and process for the preparation thereof
US5194264A (en) * 1989-03-13 1993-03-16 Scientific Chemicals (Proprietary) Limited Pesticidal formulation
EP0537447A1 (fr) * 1991-10-09 1993-04-21 DESOWAG GmbH Agent aqueux pour la protection du bois
US5506269A (en) * 1993-12-27 1996-04-09 Mitsui Toatsu Chemicals, Inc. Parasiticide employing pyrethroid type compounds
EP0665011A1 (fr) * 1993-12-27 1995-08-02 Mitsui Toatsu Chemicals, Incorporated Parasiticide contre des endoparasites contenant un composé de type pyréthroide
WO2000047048A1 (fr) * 1999-02-08 2000-08-17 Virbac (Australia) Pty. Limited Traitement a pesticides
EP1182931A4 (fr) * 1999-06-04 2003-01-29 Nufarm Ltd Compositions biocides stables
EP1414304A1 (fr) 2001-07-25 2004-05-06 Syngenta Limited Melange insecticide contenant de la gamma-cyhalothrine
EP2087791A3 (fr) * 2001-07-25 2009-09-16 Syngenta Limited Mélange insecticide contenant un gamma-cyhalothrine
US7906127B2 (en) 2001-07-25 2011-03-15 Syngenta Limited Insecticidal mixture containing gamma-cyhalothrin
US8852618B2 (en) 2001-07-25 2014-10-07 Syngenta Limited Insecticidal mixture containing gamma-cyhalothrin
EP2260708A3 (fr) * 2001-07-25 2015-04-15 Syngenta Limited Mélange insecticide contenant un gamma-cyhalothrine
CN102771499A (zh) * 2012-07-09 2012-11-14 启东市中勇机电工具有限公司 无毒灭蝇剂

Also Published As

Publication number Publication date
GB8614989D0 (en) 1986-07-23
AU595225B2 (en) 1990-03-29
AU6126386A (en) 1987-01-13
GB8515459D0 (en) 1985-07-24
GB2176706A (en) 1987-01-07
GB2176706B (en) 1989-07-19
EP0259340A1 (fr) 1988-03-16

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